JP2017204492A - Organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element which is excellent in luminous efficiency, drive voltage and life.SOLUTION: Provided is an organic EL element in which a hole transport layer contains a compound represented by a formula (1) and a luminous layer contains an amine derivative having a condensed ring structure of a particular structure.SELECTED DRAWING: None

Description

The present invention relates to an organic electroluminescence element which is a self-luminous element suitable for various display devices. Specifically, the present invention relates to a specific arylamine compound and the compound (and a compound having a pyrimidine ring structure having a specific structure). The present invention relates to an organic electroluminescent element (hereinafter, abbreviated as an organic EL element) using the above.

  Since organic EL elements are self-luminous elements, they have been actively researched because they are brighter and have better visibility than liquid crystal elements and can display clearly.

In 1987, Eastman Kodak's C.I. W. Tang et al. Have made a practical organic EL device using an organic material by developing a laminated structure device in which various roles are assigned to each material. They laminate a phosphor capable of transporting electrons and an organic substance capable of transporting holes, and inject both charges into the phosphor layer to emit light. High luminance of 1000 cd / m ² or more can be obtained (for example, see Patent Document 1 and Patent Document 2).

  Up to now, many improvements have been made for practical use of organic EL devices, and the various roles of the laminated structure have been further subdivided, and sequentially on the substrate, anode, hole injection layer, hole transport layer, light emitting layer High efficiency and durability have been achieved by electroluminescent devices provided with an electron transport layer, an electron injection layer, and a cathode (see, for example, Non-Patent Document 1).

Further, the use of triplet excitons has been attempted for the purpose of further improving the light emission efficiency, and the use of phosphorescent compounds has been studied (see, for example, Non-Patent Document 2).
An element utilizing light emission by thermally activated delayed fluorescence (TADF) has also been developed. In 2011, Adachi et al. Of Kyushu University realized an external quantum efficiency of 5.3% with a device using a thermally activated delayed fluorescent material. (For example, see Non-Patent Document 3)

The light emitting layer can also be manufactured by doping a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence. As described in the non-patent document, selection of an organic material in an organic EL element greatly affects various characteristics such as efficiency and durability of the element. (For example, see Non-Patent Document 2)

In the organic EL element, the light injected from both electrodes is recombined in the light emitting layer to obtain light emission, but it is important how efficiently both holes and electrons are transferred to the light emitting layer. It is necessary to make the device excellent in carrier balance. In addition, the probability of recombination of holes and electrons is improved by improving the hole injection property and blocking the electron injected from the cathode, and further excitons generated in the light emitting layer. By confining, high luminous efficiency can be obtained. Therefore, the role of the hole transport material is important, and there is a demand for a hole transport material that has high hole injectability, high hole mobility, high electron blocking properties, and high durability against electrons. ing.

In addition, the heat resistance and amorphousness of the material are also important for the lifetime of the element. In a material having low heat resistance, thermal decomposition occurs even at a low temperature due to heat generated when the element is driven, and the material is deteriorated. In the case of a material having low amorphous property, the thin film is crystallized even in a short time, and the element is deteriorated. For this reason, the material used is required to have high heat resistance and good amorphous properties.

N, N′-diphenyl-N, N′-di (α-naphthyl) benzidine (NPD) and various aromatic amine derivatives are known as hole transport materials that have been used in organic EL devices. (For example, see Patent Document 1 and Patent Document 2). NPD has a good hole transport capability, but its glass transition point (Tg), which is an index of heat resistance, is as low as 96 ° C., and device characteristics are degraded due to crystallization under high temperature conditions (for example, Non-patent document 4). Further, among the aromatic amine derivatives described in the above-mentioned patent documents, compounds having excellent mobility such as hole mobility of 5 ⁻³ cm ² / Vs or more are known (for example, patent documents) 1 and Patent Document 2), since the electron blocking property is insufficient, a part of the electrons pass through the light emitting layer, and the improvement of the light emission efficiency cannot be expected. Therefore, there has been a demand for a material having high heat resistance, a more stable thin film, and high heat resistance. Further, although there is a report of a highly durable aromatic amine derivative (see, for example, Patent Document 3), it was used as a charge transport material used in an electrophotographic photoreceptor, and there was no example used as an organic EL device. .

Although arylamine compounds having a substituted carbazole structure have been proposed as compounds with improved characteristics such as heat resistance and hole injection properties (see, for example, Patent Document 4 and Patent Document 5), these compounds are injected with holes. Although the elements used for the layer or the hole transport layer have been improved in heat resistance, luminous efficiency, etc., they are still not sufficient, and further lower driving voltage and higher luminous efficiency are required. .

By combining materials with excellent hole and electron injection / transport performance, thin film stability and durability, in order to improve the device characteristics of organic EL devices and improve the yield of device fabrication, the number of holes and electrons can be increased. There is a need for an element that can recombine efficiently, has high luminous efficiency, low driving voltage, and long life.

In addition, in order to improve the device characteristics of organic EL devices, high efficiency and low drive with a balanced carrier are achieved by combining materials with excellent hole and electron injection / transport performance, thin film stability and durability. There is a need for a device that has a voltage and a long lifetime.

JP-A-8-048656 Japanese Patent No. 3194657 Japanese Patent No. 4943840 JP 2006-151979 A International Publication No. 2008/62636 International Publication No. 2005/115970 International Publication No. 2013/054764 International Publication No. 2014/009310

Proceedings of the 9th meeting of the Japan Society of Applied Physics 55-61 pages (2001) Proceedings of the 9th Workshop of the Japan Society of Applied Physics 23-31 pages (2001) Appl. Phys. Let. 98,083302 (2011) Proceedings of the 3rd Regular Meeting of the Organic EL Discussion Group, 13-14 pages (2006)

The object of the present invention is as a material for an organic EL device having high efficiency and high durability, and for an organic EL device excellent in hole injection / transport performance, electron blocking capability, stability in a thin film state, and durability. In addition, the materials and various materials for organic EL elements having excellent hole and electron injection / transport performance, electron blocking ability, stability in a thin film state, and durability, It is an object of the present invention to provide an organic EL element with high efficiency, low driving voltage, and long life by combining them so that the characteristics of these materials can be effectively expressed.

The physical properties that the organic compound to be provided by the present invention should have include (1) good hole injection properties, (2) high hole mobility, and (3) a thin film state. It can be mentioned that it is stable and (4) it has excellent heat resistance. Further, the physical characteristics to be provided by the organic EL element to be provided by the present invention are (1) high luminous efficiency and power efficiency, (2) low emission start voltage, and (3) practical driving. Low voltage and (4) long life can be mentioned.

Therefore, in order to achieve the above object, the inventors of the present invention are that the arylamine-based material has excellent hole injection and transport capability, thin film stability and durability, and luminous efficiency of the amine derivative having a condensed ring structure. In order to efficiently inject and transport holes to the light-emitting layer by selecting a specific arylamine compound and an amine derivative having a condensed ring structure having a specific structure. Various organic EL elements in which a transport material and a light-emitting material are combined were produced, and the characteristics of the elements were earnestly evaluated. In addition, paying attention to the fact that a compound having a pyrimidine ring structure is excellent in electron injection and transport capability, and stability and durability of a thin film, a compound having a specific pyrimidine ring structure is selected, and electrons in the light-emitting layer are selected. Various organic EL devices that combine hole transport materials, light-emitting materials, and electron-transport materials are manufactured so as to improve injection / transport efficiency and achieve a carrier balance that matches the properties of the light-emitting materials. I did it. Furthermore, the hole transport layer has a two-layer structure of a first hole transport layer and a second hole transport layer, and two specific types of arylamine compounds are selected to inject holes more efficiently into the light emitting layer. Select a material for the first hole transport layer so that it can be transported, select a material with excellent electron blocking properties as the material for the second hole transport layer, and combine the carrier balance with the characteristics of the light emitting material. Various refined organic EL elements were produced and the characteristics of the elements were earnestly evaluated. As a result, the present invention has been completed.

That is, according to the present invention, the following organic EL elements are provided.

1) In an organic electroluminescence device having at least an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole transport layer contains an arylamine compound represented by the following general formula (1). And the said light emitting layer contains the amine derivative which has a condensed ring structure represented by following General formula (2), The organic EL element characterized by the above-mentioned.

（１）

(1)

(In the formula, Ar _{1 to} Ar ₄ may be the same as or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic ring. R ₁ represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent. A cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a substituent. A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, substituted or unsubstituted Aromatic hydrocarbon group, A substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, r ₁ represents an integer of ₁ to 4, and r ₁ is 2. In the case where it is an integer of ˜4, a plurality of R ₁ bonded to the same benzene ring may be the same or different from each other, and bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. Where Ar ₁ and Ar ₂ , Ar ₃ and Ar ₄ may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom, or sulfur atom. A ring may be formed.)

(In the formula, A ₁ is a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, Or represents a single bond, and Ar ₅ and Ar ₆ may be the same or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted condensed groups A polycyclic aromatic group which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring, and R _{2 to} R ₅ may be the same as each other. May be different, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, Optionally substituted 5 carbon atoms Or a cycloalkyl group having 10 carbon atoms, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a straight chain having 1 to 6 carbon atoms which may have a substituent. A linear or branched alkyloxy group, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic complex; Substituted with a group selected from a cyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, each group may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring, R ₂ to In the benzene ring to which R ₅ is bonded, any one group of R _{2 to} R ₅ is removed, and the removed part and other groups of R _{2 to} R ₅ are substituted or unsubstituted methylene groups, oxygen A ring may be bonded to each other via an atom, a sulfur atom, or a monosubstituted amino group, and R _{6 to} R ₈ may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, A chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyl group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a linear chain having 1 to 6 carbon atoms which may have a substituent Or branched alkyloxy group, substituted A cycloalkyloxy group having 5 to 10 carbon atoms which may have a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycycle An aromatic group, or a substituted or unsubstituted aryloxy group, each group being bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring Alternatively, in the benzene ring to which R _{6 to} R ₈ are bonded, any one group of R _{6 to} R ₈ is removed, and the removed part and the other group of R _{6 to} R ₈ are substituted or unsubstituted. It may be bonded to each other via a substituted methylene group, oxygen atom, sulfur atom, or monosubstituted amino group to form a ring. R ₉ and R ₁₀ may be the same or different from each other, and may have a substituent, a linear or branched alkyl group having 1 to 6 carbon atoms, or a substituent. A cycloalkyl group having 5 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, substituted or An unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, each group being a single bond, a substituted or unsubstituted methylene group, A ring may be formed by bonding to each other via an oxygen atom, a sulfur atom, or a monosubstituted amino group. )

2) The electron transport layer contains a compound having a pyrimidine ring structure represented by the following general formula (3) or a compound having a benzotriazole ring structure represented by the following general formula (4). The organic EL device according to 1) above.

(In the formula, Ar ₇ represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group, and Ar ₈ and Ar ₉ may be the same or different, and each represents a hydrogen atom. Represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group, Ar ₁₀ represents a substituted or unsubstituted aromatic heterocyclic group, and R _{11 to} R ₁₄ represent , Which may be the same or different, hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, trifluoromethyl group, linear or branched alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted An aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein Ar ₈ and Ar ₉ are not hydrogen atoms at the same time Toss )

（４）

(4)

(In the formula, Ar ₁₁ represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, Ar ₁₂ represents a hydrogen atom, A deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and A ₂ represents a substituted or unsubstituted aromatic Represents a divalent group of an aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and A ₃ represents a substituted or unsubstituted group Represents a condensed polycyclic aromatic divalent group or a single bond, and B ₁ represents a substituted or unsubstituted aromatic heterocyclic group.)

3) In an organic electroluminescence device having at least an anode, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole transport layer is an arylamine represented by the general formula (1) The organic EL device according to 1) or 2) above, which contains a compound and the electron blocking layer contains an arylamine compound represented by the following general formula (5) or (6).

（５）

(5)

(In the formula, Ar _{13 to} Ar ₁₆ may be the same as or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted condensed polycyclic rings. Represents an aromatic group.)

（６）

(6)

(Wherein, Ar ₁₇ to Ar ₂₀ may be the same or different, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic, Represents an aromatic group, and n1 represents an integer of 2 to 4.)

4) In an organic electroluminescence device having at least an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole injection layer is represented by the general formula (1). An arylamine compound and an electron acceptor, wherein the electron acceptor is trisbromophenylamine hexachloroantimony, tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1, 4. The organic EL device according to any one of 1) to 3) above, which is an electron acceptor selected from 4-benzoquinone dimethane (F4TCNQ) and a radialene derivative.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by Ar _{1 to} Ar ₄ in the general formula (1), or “substituted or unsubstituted condensed hydrocarbon group” As the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “ring aromatic group”, specifically, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group Group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group Group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group Quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, and the like acridinyl group, and carbolinyl group.
Here, Ar ₁ and Ar ₂ , Ar ₃ and Ar ₄ may be bonded to each other via a single bond or a substituted or unsubstituted methylene group, oxygen atom, or sulfur atom to form a ring.

As the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar _{1 to} Ar ₄ in the general formula (1), Specifically, deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group, ethyloxy group, propyl Straight or branched alkyloxy groups having 1 to 6 carbon atoms such as oxy groups; alkenyl groups such as vinyl groups and allyl groups; phenyloxy groups, tolyloxy groups, etc. Aryloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoran Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as tenenyl group and triphenylenyl group; pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group , Indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group, etc. An aryl vinyl group such as a styryl group or a naphthyl vinyl group; a group such as an acyl group such as an acetyl group or a benzoyl group. These substituents may be substituted by the above-described substituents. good. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

“A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent” represented by R ₁ in the general formula (1), “may have a substituent “C1-C6 straight chain or branched alkenyl group having 2 to 6 carbon atoms which may be substituted” or “C1-C6 straight chain”. Specific examples of the “chain or branched alkyl group”, “cycloalkyl group having 5 to 10 carbon atoms” or “linear or branched alkenyl group having 2 to 6 carbon atoms” specifically include a methyl group , Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, cyclopentyl group, cyclohexyl Group, 1-adamantyl group, 2-adamantyl group, vinyl group, allyl group, isopropenyl group, 2-butenyl group and the like. When r ₁ is an integer of 2 to 4, a plurality of R ₁ bonded to the same benzene ring may be the same or different from each other, and may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be bonded to each other through a benzene ring to which R ₁ and R ₁ are directly bonded, such as a substituted or unsubstituted methylene group, oxygen atom, sulfur atom, monosubstituted amino group, etc. A ring may be formed by bonding to each other via a linking group.

“A linear or branched alkyl group having 1 to 6 carbon atoms having a substituent” represented by R ₁ in the general formula (1), “cycloalkyl having 5 to 10 carbon atoms having a substituent” Specific examples of the “substituent” in the “group” or “straight-chain or branched alkenyl group having 2 to 6 carbon atoms having a substituent” include deuterium atom, cyano group, nitro group; fluorine atom, Halogen atoms such as chlorine, bromine and iodine atoms; linear or branched alkyloxy groups having 1 to 6 carbon atoms such as methyloxy, ethyloxy and propyloxy groups; vinyl and allyl groups Alkenyl groups; aryloxy groups such as phenyloxy groups and tolyloxy groups; arylalkyloxy groups such as benzyloxy groups and phenethyloxy groups; Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as phenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; pyridyl Group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyrrolyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group Aromatic heterocyclic groups such as pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group; disubstituted by aromatic hydrocarbon group such as diphenylamino group, dinaphthylamino group or condensed polycyclic aromatic group A substituted amino group; a disubstituted amino group substituted with an aromatic heterocyclic group such as a dipyridylamino group or a dithienylamino group; selected from an aromatic hydrocarbon group, a condensed polycyclic aromatic group or an aromatic heterocyclic group Examples thereof include a group such as a di-substituted amino group substituted with a substituent, and these substituents may be further substituted with the above-exemplified substituents. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

“A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent” represented by R ₁ in the general formula (1) or “having a substituent. The term “a linear or branched alkyloxy group having 1 to 6 carbon atoms” or “cycloalkyloxy group having 5 to 10 carbon atoms” in “a cycloalkyloxy group having 5 to 10 carbon atoms”. Specifically, methyloxy group, ethyloxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group, cyclohexyloxy Group, cycloheptyloxy group, cyclooctyloxy group, 1-adamantyloxy group, 2-adamantyloxy group, etc. I can make it. When r ₁ is an integer of 2 to 4, a plurality of R ₁ bonded to the same benzene ring may be the same or different from each other, and may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be bonded to each other through a benzene ring to which R ₁ and R ₁ are directly bonded, such as a substituted or unsubstituted methylene group, oxygen atom, sulfur atom, monosubstituted amino group, etc. A ring may be formed by bonding to each other via a linking group.
In addition, R ₁ may have a substituent, and the substituent is represented by R ₁ in the general formula (1), which is “linear or branched having 1 to 6 carbon atoms having a substituent. The “substituent” in the “alkyl group”, “cycloalkyl group having 5 to 10 carbon atoms having substituent” or “linear or branched alkenyl group having 2 to 6 carbon atoms having substituent”. The same thing as what was shown can be mention | raise | lifted and the aspect which can be taken can also mention the same thing.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R ₁ in the general formula (1) or “substituted or unsubstituted condensed polycyclic aromatic” As the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “group”, specifically, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl Group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyridyl group, pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzo Thienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxaly Nyl group, benzimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthyridinyl group, phenanthrolinyl group, acridinyl group, carbolinyl group and the like can be mentioned. When r ₁ is an integer of 2 to 4, a plurality of R ₁ bonded to the same benzene ring may be the same or different from each other, and may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be bonded to each other through a benzene ring to which R ₁ and R ₁ are directly bonded, such as a substituted or unsubstituted methylene group, oxygen atom, sulfur atom, monosubstituted amino group, etc. A ring may be formed by bonding to each other via a linking group.
In addition, R ₁ may have a substituent, and the substituent is represented by R ₁ in the general formula (1), which is “linear or branched having 1 to 6 carbon atoms having a substituent. The “substituent” in the “alkyl group”, “cycloalkyl group having 5 to 10 carbon atoms having substituent” or “linear or branched alkenyl group having 2 to 6 carbon atoms having substituent”. The same thing as what was shown can be mention | raise | lifted and the aspect which can be taken can also mention the same thing.

Specific examples of the “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R ₁ in the general formula (1) include a phenyloxy group, a biphenylyloxy group, and a terphenylyloxy group. Naphthyloxy group, anthracenyloxy group, phenanthrenyloxy group, fluorenyloxy group, indenyloxy group, pyrenyloxy group, perylenyloxy group, and the like. When r ₁ is an integer of 2 to 4, a plurality of R ₁ bonded to the same benzene ring may be the same or different from each other, and may be a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be bonded to each other through a benzene ring to which R ₁ and R ₁ are directly bonded, such as a substituted or unsubstituted methylene group, oxygen atom, sulfur atom, monosubstituted amino group, etc. A ring may be formed by bonding to each other via a linking group.
In addition, these groups may have a substituent, and the substituent is represented by R ₁ in the general formula (1), which is a linear or branched group having 1 to 6 carbon atoms having a substituent. "Substituent" in "Cyclic alkyl group having 5 to 10 carbon atoms having substituent" or "Linear or branched alkenyl group having 2 to 6 carbon atoms having substituent" The thing similar to what was shown regarding can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

The “divalent group of a substituted or unsubstituted aromatic hydrocarbon”, “divalent group of a substituted or unsubstituted aromatic heterocycle” represented by A ₁ in the general formula (2) or “substituted or unsubstituted “Substituted or unsubstituted aromatic hydrocarbon”, “substituted or unsubstituted aromatic heterocycle” or “substituted or unsubstituted condensed polycyclic aromatic” in “substituted condensed polycyclic aromatic divalent group” Specific examples of the “aromatic hydrocarbon”, “aromatic heterocycle” or “fused polycyclic aromatic” include benzene, biphenyl, terphenyl, tetrakisphenyl, styrene, naphthalene, anthracene, acenaphthalene, fluorene, phenanthrene. , Indane, pyrene, triphenylene, pyridine, pyrimidine, triazine, pyrrole, furan, thiophene, quinoline, isoquinoline, benzofuran, benzothi Examples include offene, indoline, carbazole, carboline, benzoxazole, benzothiazole, quinoxaline, benzimidazole, pyrazole, dibenzofuran, dibenzothiophene, naphthyridine, phenanthroline, acridinine, and the like.
In addition, “a divalent group of a substituted or unsubstituted aromatic hydrocarbon”, “a divalent group of a substituted or unsubstituted aromatic heterocycle” represented by A ₁ in the general formula (2), or “substituted or The “unsubstituted fused polycyclic aromatic divalent group” is a divalent group formed by removing two hydrogen atoms from the above “aromatic hydrocarbon”, “aromatic heterocycle” or “fused polycyclic aromatic”. Represent.
In addition, these divalent groups may have a substituent. Specific examples of the substituent include a deuterium atom, a cyano group, and a nitro group; a halogen such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Atom: 1 carbon atom such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group A linear or branched alkyl group having 6 to 6 carbon atoms; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethyloxy group, or a propyloxy group; an alkenyl group such as an allyl group; Aryloxy groups such as phenyloxy group and tolyloxy group; arylalkyloxy groups such as benzyloxy group and phenethyloxy group; phenyl Aromatic hydrocarbon groups or condensed polycyclic aromatic groups such as biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group; Pyridyl, pyrimidinyl, triazinyl, thienyl, furyl, pyrrolyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl Group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group and other aromatic heterocyclic groups; styryl group, naphthylvinyl group and other aryl vinyl groups; acetyl group, benzoyl group and other acyl groups; Trimethylsilyl group, can be mentioned groups such as silyl groups such as triphenylsilyl group, these substituents may further the exemplified substituents may be substituted. These substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by Ar ₅ or Ar ₆ in the general formula (2), or “substituted or unsubstituted condensed poly group” The “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “ring aromatic group” is represented by Ar _{1 to} Ar ₄ in the general formula (1). “Aromatic hydrocarbon group”, “aromatic” in “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” And the same as those shown for the “aromatic heterocyclic group” or “fused polycyclic aromatic group”, and Ar ₅ and Ar ₆ are a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. May be linked to each other via a ring to form a ring. .
In addition, these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group” or a “substituted aromatic complex” represented by Ar _{1 to} Ar ₄ in the general formula (1). The same thing as what was shown regarding the "substituent" in a "ring group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

“A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent” represented by R _{2 to} R ₈ in the general formula (2), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “straight or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”. The “6 linear or branched alkyl group”, “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group” includes the above general formula (1) The “optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ , “optionally substituted carbon” A cycloalkyl group having 5 to 10 atoms "or" substitution The “straight or branched alkyl group having 1 to 6 carbon atoms” in the “linear or branched alkenyl group having 2 to 6 carbon atoms which may have a group”, “5 carbon atoms”. Examples thereof are the same as those shown for “C10 to C10 cycloalkyl group” or “C2-C6 linear or branched alkenyl group”.
In addition, these groups may have a substituent, and as the substituent, “a linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). ”,“ C 5 -C 10 cycloalkyl group ”or“ C 2 -C 6 linear or branched alkenyl group ”, the same as those described for“ Substituent ”. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

“A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent” represented by R _{2 to} R ₈ in the general formula (2) or “having a substituent. Or a "C1-C6 linear or branched alkyloxy group" or "C5-C10 cycloalkyloxy group" in the "optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms". "Is a" linear or branched alkyloxy group having 1 to 6 carbon atoms which may have a substituent "represented by R ₁ in the general formula (1) or" substituent A “linear or branched alkyloxy group having 1 to 6 carbon atoms” or “cycloalkyl having 5 to 10 carbon atoms” in the “cycloalkyloxy group having 5 to 10 carbon atoms” which may have Oh The thing similar to what was shown regarding "xy group" can be mention | raise | lifted.
In addition, these groups may have a substituent, and as the substituent, “a linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). ”,“ C 5 -C 10 cycloalkyl group ”or“ C 2 -C 6 linear or branched alkenyl group ”, the same as those described for“ Substituent ”. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R _{2 to} R ₈ in the general formula (2) or “substituted or unsubstituted condensed hydrocarbon group” The “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “ring aromatic group” is the “substituted or represented by R ₁ in the general formula (1)”. “Aromatic hydrocarbon group”, “aromatic heterocycle” in “unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” Group "or" condensed polycyclic aromatic group "can be mentioned, and these groups can be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. These groups may be bonded to form a ring (R _{2 to} R ₈ ) and a benzene ring to which these groups (R _{2 to} R ₈ ) are directly bonded, and a linking group such as a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, and a monosubstituted amino group. And may be bonded to each other to form a ring.
In addition, these groups may have a substituent, and as the substituent, “a linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). ”,“ C 5 -C 10 cycloalkyl group ”or“ C 2 -C 6 linear or branched alkenyl group ”, the same as those described for“ Substituent ”. These groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring, and these groups (R _{2 to} R ₈ ) and these And a benzene ring to which the groups (R _{2 to} R ₈ ) are directly bonded, and bonded to each other via a linking group such as a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monosubstituted amino group. May be formed.

The “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R _{2 to} R ₈ in the general formula (2) is represented by R ₁ in the general formula (1). The same thing as what was shown regarding "aryloxy group" in "substituted or unsubstituted aryloxy group" can be mention | raise | lifted, and these groups are a single bond, a substituted or unsubstituted methylene group, an oxygen atom, or a sulfur atom. May be bonded to each other through a ring, and these groups (R _{2 to} R ₈ ) and a benzene ring to which these groups (R _{2 to} R ₈ ) are directly bonded may be substituted or unsubstituted. A ring may be formed by bonding to each other via a linking group such as a substituted methylene group, an oxygen atom, a sulfur atom, or a monosubstituted amino group.
In addition, these groups may have a substituent, and as the substituent, “a linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). ”,“ C 5 -C 10 cycloalkyl group ”or“ C 2 -C 6 linear or branched alkenyl group ”, the same as those described for“ Substituent ”. These groups may be bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.

“Disubstituted amino group substituted by a group selected from aromatic hydrocarbon group, aromatic heterocyclic group or condensed polycyclic aromatic group” represented by R _{2 to} R ₅ in general formula (2) Examples of the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” include “substituted or unsubstituted aromatic” represented by Ar _{1 to} Ar ₄ in the general formula (1). "Aromatic hydrocarbon group", "substituted or unsubstituted aromatic heterocyclic group" or "substituted or unsubstituted condensed polycyclic aromatic group" in "aromatic hydrocarbon group", "aromatic heterocyclic group" or " The thing similar to what was shown regarding "the condensed polycyclic aromatic group" can be mention | raise | lifted.
In addition, these groups may have a substituent, and as the substituent, “a linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). ”,“ C 5 -C 10 cycloalkyl group ”or“ C 2 -C 6 linear or branched alkenyl group ”, the same as those described for“ Substituent ”. A possible embodiment can also be given.
The “disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group” represented by R _{2 to} R ₅ in the general formula (2) is: these groups _(R 2 ~R ₅₎ to each other, these groups _(R 2 ~R ₅₎ has the "aromatic hydrocarbon group", the "aromatic heterocyclic group" or "condensed polycyclic aromatic group" _May be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring, and these groups (R _{2 to} R ₅ ) and these groups (R ₂ to R ₅₎ is in the benzene ring bonded directly, these groups _(R 2 ~R ₅₎ has the "aromatic hydrocarbon group", "aromatic heterocyclic group" or "condensed polycyclic aromatic A substituted or unsubstituted methylene group, oxygen atom, sulfur atom, monosubstituted amino It may be bonded to each other to form a ring through a linking group such as.

“A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent” represented by R ₉ or R ₁₀ in the general formula (2), “having a substituent In the “cycloalkyl group having 5 to 10 carbon atoms” or “straight or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”. The “6 linear or branched alkyl group”, “C 5 -C 10 cycloalkyl group” or “C 2 -C 6 linear or branched alkenyl group” includes the above general formula (1) The “optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ , “optionally substituted carbon” A cycloalkyl group having 5 to 10 atoms "or" position “Linear or branched alkyl group having 1 to 6 carbon atoms” in “linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”, “number of carbon atoms” Examples thereof include those similar to those shown for “5 to 10 cycloalkyl group” or “linear or branched alkenyl group having 2 to 6 carbon atoms”, and these groups are single-bonded or substituted. Alternatively, they may be bonded to each other via a linking group such as an unsubstituted methylene group, an oxygen atom, a sulfur atom, or a monosubstituted amino group to form a ring.
In addition, these groups may have a substituent, and as the substituent, “a linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). , "The same as those shown for the" substituent "in the" cycloalkyl group having 5 to 10 carbon atoms "or" the linear or branched alkenyl group having 2 to 6 carbon atoms ". The possible modes are the same.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by R ₉ or R ₁₀ in the general formula (2), or “substituted or unsubstituted condensed poly group” The “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “ring aromatic group” is the “substituted or represented by R ₁ in the general formula (1)”. “Aromatic hydrocarbon group”, “aromatic heterocycle” in “unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” Examples thereof include those similar to those shown for the “group” or “fused polycyclic aromatic group”, and these groups are a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, a monosubstituted amino group. Bond to each other via a linking group such as a group to form a ring May be.
In addition, these groups may have a substituent, and as the substituent, “a linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). ”,“ C 5 -C 10 cycloalkyl group ”or“ C 2 -C 6 linear or branched alkenyl group ”, the same as those described for“ Substituent ”. A possible embodiment can also be given.

The “aryloxy group” in the “substituted or unsubstituted aryloxy group” represented by R ₉ and R ₁₀ in the general formula (2) is represented by R ₁ in the general formula (1). The same thing as what was shown regarding "aryloxy group" in "substituted or unsubstituted aryloxy group" can be mention | raise | lifted, and these groups are a single bond, a substituted or unsubstituted methylene group, an oxygen atom, and a sulfur atom. And may be bonded to each other via a linking group such as a monosubstituted amino group to form a ring.
In addition, these groups may have a substituent, and as the substituent, “a linear or branched alkyl group having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). ”,“ C 5 -C 10 cycloalkyl group ”or“ C 2 -C 6 linear or branched alkenyl group ”, the same as those described for“ Substituent ”. A possible embodiment can also be given.

The “substituent” in the linking group “monosubstituted amino group” in the general formula (2) is “linear or branched having 1 to 6 carbon atoms” represented by R ₁ in the general formula (1). The same as those described for the “substituent” in the “alkyl group”, “cycloalkyl group having 5 to 10 carbon atoms” or “straight or branched alkenyl group having 2 to 6 carbon atoms” Examples of possible modes are the same.

“Aromatics” in the “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted condensed polycyclic aromatic group” represented by Ar ₇ , Ar ₈ , Ar ₉ in the general formula (3) Specific examples of the `` hydrocarbon group '' or `` fused polycyclic aromatic group '' include phenyl group, biphenylyl group, terphenylyl group, quarterphenyl group, styryl group, naphthyl group, anthracenyl group, acenaphthenyl group, phenanthrenyl group, and fluorenyl group. And groups such as indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, and triphenylenyl group.
In addition, these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group” or a “substituted aromatic complex” represented by Ar _{1 to} Ar ₄ in the general formula (1). The same thing as what was shown regarding the "substituent" in a "ring group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

As the “aromatic heterocyclic group” in the “substituted or unsubstituted aromatic heterocyclic group” represented by Ar ₁₀ in the general formula (3), specifically, a triazinyl group, a pyridyl group, a pyrimidinyl group, Furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group And a group such as a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl group, an acridinyl group, and a carbolinyl group.
In addition, these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group” or a “substituted aromatic complex” represented by Ar _{1 to} Ar ₄ in the general formula (1). The same thing as what was shown regarding the "substituent" in a "ring group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

Specific examples of the “linear or branched alkyl group having 1 to 6 carbon atoms” represented by R _{11 to} R ₁₄ in the general formula (3) include a methyl group, an ethyl group, n- Propyl group, i-propyl group, n-butyl group, 2-methylpropyl group, t-butyl group, n-pentyl group, 3-methylbutyl group, tert-pentyl group, n-hexyl group, iso-hexyl group and tert -A hexyl group can be mentioned.

The “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensation” represented by R _{11 to} R ₁₄ in the general formula (3) As the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “polycyclic aromatic group”, specifically, phenyl group, biphenylyl group, terphenylyl group, quarterphenyl group , Styryl group, naphthyl group, anthracenyl group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, triazinyl group, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group , Thienyl, quinolyl, isoquinolyl, benzofuranyl, benzothienyl, indolyl, Examples include groups such as bazolyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzimidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, naphthyridinyl, phenanthrolinyl, acridinyl, and carbolinyl. be able to.
In addition, these groups may have a substituent, and as the substituent, in the general formula (1), a “substituted aromatic hydrocarbon group” represented by Ar _{1 to} Ar ₄ , “substituted aromatic complex” The same thing as what was shown regarding the "substituent" in a "ring group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by Ar ₁₁ or Ar ₁₂ in the general formula (4), or “substituted or unsubstituted condensed poly group” The “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “ring aromatic group” is represented by Ar _{1 to} Ar ₄ in the general formula (1). “Aromatic hydrocarbon group”, “aromatic” in “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” The same as those shown for the “aromatic heterocyclic group” or “fused polycyclic aromatic group”, and Ar ₁₁ and Ar ₁₂ are a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. Bond to each other via It may be.
In addition, these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group” or a “substituted aromatic complex” represented by Ar _{1 to} Ar ₄ in the general formula (1). The same thing as what was shown regarding the "substituent" in a "ring group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

Represented by A ₂ in the general formula (4), “a divalent group of a substituted or unsubstituted aromatic hydrocarbon”, “a divalent group of a substituted or unsubstituted aromatic heterocycle” or “substituted or unsubstituted “Substituted or unsubstituted aromatic hydrocarbon”, “substituted or unsubstituted aromatic heterocycle” or “substituted or unsubstituted condensed polycyclic aromatic” in “substituted condensed polycyclic aromatic divalent group” As the “aromatic hydrocarbon”, “aromatic heterocycle” or “fused polycyclic aromatic”, “substituted or unsubstituted aromatic hydrocarbon 2” represented by A ₁ in the general formula (2) is used. "Substituted or unsubstituted aromatic hydrocarbon" in "valent group", "divalent group of substituted or unsubstituted aromatic heterocyclic ring" or "substituted or unsubstituted condensed polycyclic aromatic divalent group", " Substituted or unsubstituted aromatic heterocycle "or" substituted or unsubstituted The same thing as what was shown regarding "aromatic hydrocarbon", "aromatic heterocyclic ring", or "condensed polycyclic aromatic" of "combined polycyclic aromatic" can be mention | raise | lifted, These groups are single bonds, A ring may be formed by bonding to each other via a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom.
These divalent groups may have a substituent, and examples of the substituent include “aromatic hydrocarbon”, “aromatic heterocycle” represented by A ₁ in the general formula (2), or The same thing as what was shown regarding the "substituent" in "condensed polycyclic aromatic" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

“Condensed polycyclic aromatic” of “substituted or unsubstituted condensed polycyclic aromatic” in “substituted or unsubstituted condensed polycyclic aromatic divalent group” represented by A ₃ in formula (4) "Is a" condensation "of" substituted or unsubstituted condensed polycyclic aromatic "in" substituted or unsubstituted divalent polycyclic aromatic group "represented by A ₁ in general formula (2) Examples of the "polycyclic aromatic" include those similar to those shown above, and these groups are bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. May be.
These divalent groups may have a substituent, and examples of the substituent include “aromatic hydrocarbon”, “aromatic heterocycle” represented by A ₁ in the general formula (2), or The same thing as what was shown regarding the "substituent" in "condensed polycyclic aromatic" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

Specific examples of the “aromatic heterocyclic group” in the “substituted or unsubstituted aromatic heterocyclic group” represented by B ₁ in the general formula (4) include a pyridyl group, a bipyridyl group, a triazinyl group, Pyrimidinyl, pyrrolyl, quinolyl, isoquinolyl, indolyl, carbazolyl, carbolinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, benzoimidazolyl, pyrazolyl, naphthyridinyl, phenanthrolinyl, acridinyl Etc.
In addition, these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group” represented by Ar _{1 to} Ar ₄ in the general formula (1), “substituted aromatic” The thing similar to what was shown regarding the "substituent" in a "heterocyclic group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

The “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by Ar _{13 to} Ar ₁₆ in the general formula (5), or “substituted or unsubstituted condensed poly group” The “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “ring aromatic group” is represented by Ar _{1 to} Ar ₄ in the general formula (1). “Aromatic hydrocarbon group”, “aromatic” in “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” And the same as those shown for the “heterocyclic group” or “condensed polycyclic aromatic group”, and these groups can form a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. To form a ring There.
In addition, these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group” represented by Ar _{1 to} Ar ₄ in the general formula (1), “substituted aromatic” The thing similar to what was shown regarding the "substituent" in a "heterocyclic group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” represented by Ar _{17 to} Ar ₂₀ in the general formula (6), or “substituted or unsubstituted condensed poly group” The “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group” in the “ring aromatic group” is represented by Ar _{1 to} Ar ₄ in the general formula (1). “Aromatic hydrocarbon group”, “aromatic” in “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” And the same as those shown for the “heterocyclic group” or “condensed polycyclic aromatic group”, and these groups can form a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. To form a ring There.
In addition, these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group” represented by Ar _{1 to} Ar ₄ in the general formula (1), “substituted aromatic” The thing similar to what was shown regarding the "substituent" in a "heterocyclic group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

As Ar _{1 to} Ar ₄ in the general formula (1), “substituted or unsubstituted aromatic hydrocarbon group” is preferable, and phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group. A fluorenyl group is more preferable.
As R ₁ in the general formula (1), a “substituted or unsubstituted aromatic hydrocarbon group” is preferable, and a phenyl group, a biphenylyl group, a naphthyl group, and a fluorenyl group are more preferable.
In the general formula (1), r ₁ represents an integer of ₁ to 4, but 1 or 2 is preferable.

A ₁ in the general formula (2) is preferably a “divalent group of a substituted or unsubstituted aromatic hydrocarbon” or a single bond, which is formed by removing two hydrogen atoms from benzene, biphenyl, or naphthalene. A valent group or a single bond is more preferable, and a single bond is particularly preferable.
Ar ₅ and Ar ₆ in the general formula (2) are preferably a phenyl group, a biphenylyl group, a naphthyl group, a fluorenyl group, an indenyl group, a pyridyl group, a dibenzofuranyl group, and a pyridobenzofuranyl group.
Ar ₅ and Ar ₆ in the general formula (2) are bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom, directly or through a substituent of the group. A ring may be formed.
In R _{2 to} R ₅ in the general formula (2), at least one is “a disubstituted amino group substituted by a group selected from an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group”. In this case, the “aromatic hydrocarbon group”, “aromatic heterocyclic group”, and “condensed polycyclic aromatic group” include a phenyl group, a biphenylyl group, a naphthyl group, a fluorenyl group, and an indenyl group. , A pyridyl group, a dibenzofuranyl group, and a pyridobenzofuranyl group are preferable.

In the general formula (2), two adjacent R _{2 to} R ₅ or all are vinyl groups, and the two adjacent vinyl groups are bonded to each other through a single bond to form a condensed ring, A mode in which a naphthalene ring or a phenanthrene ring is formed together with a benzene ring to which R _{2 to} R ₅ are bonded is also preferable.
In the general formula (2), any one of R _{2 to} R ₅ is an “aromatic hydrocarbon group”, a benzene ring to which R _{2 to} R ₅ are bonded, a substituted or unsubstituted methylene group, An embodiment in which a ring is bonded to each other via an oxygen atom or a sulfur atom is preferable. In this case, the “aromatic hydrocarbon group” is a phenyl group, and the benzene ring to which R _{2 to} R ₅ are bonded to each other via an oxygen atom or a sulfur atom to form a ring, The embodiment in which a dibenzofuran ring or a dibenzothiophene ring is formed together with the benzene ring to which R _{2 to} R ₅ are bonded is particularly preferred.
In the general formula (2), any one of R _{6 to} R ₈ is an “aromatic hydrocarbon group”, a benzene ring to which R _{6 to} R ₈ are bonded, a substituted or unsubstituted methylene group, An embodiment in which a ring is bonded to each other via an oxygen atom or a sulfur atom is preferable. In this case, the “aromatic hydrocarbon group” is a phenyl group, and the benzene ring to which R _{6 to} R ₈ are bonded is bonded to each other via an oxygen atom or a sulfur atom to form a ring, An embodiment in which a dibenzofuran ring or a dibenzothiophene ring is formed with a benzene ring to which R _{6 to} R ₈ are bonded is particularly preferable.
As described above, in the amine derivative having a condensed ring structure represented by the general formula (2), an aspect in which R _{2 to} R ₈ are bonded to each other to form a ring, or R ₂ As an embodiment in which ˜R ₈ and a benzene ring to which R _{2 to} R ₈ are bonded to each other form a ring, the following general formulas (2a-a), (2a-b), (2b-a), An embodiment represented by (2b-b), (2b-c), (2b-d), (2c-a) or (2c-b) is preferably used.

(In the formula, X and Y may be the same or different and each represents an oxygen atom or a sulfur atom, and A ₁ , Ar ₅ , Ar ₆ , R _{2 to} R ₅ , R _{8 to} R ₁₀ are each represented by the above general formula ( The meaning is as shown in 2).

R ₉ and R ₁₀ in the general formula (2) are “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted oxygen-containing aromatic heterocyclic group” or “substituted or unsubstituted condensed group”. A “polycyclic aromatic group” is preferable, and a phenyl group, a naphthyl group, a phenanthrenyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, and a dibenzofuranyl group are more preferable, and a phenyl group is particularly preferable.
An embodiment in which R ₉ and R ₁₀ are bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, a monosubstituted amino group or the like to form a ring is preferable. An embodiment in which a ring is bonded to each other through a bond is particularly preferable.
As described above, among the amine derivatives having a condensed ring structure represented by the general formula (2), as an embodiment in which R ₉ and R ₁₀ are bonded to each other to form a ring, the following general formula (2a-a1) , (2a-b1), (2b-a1), (2b-b1), (2b-c1), (2b-d1), (2c-a1) or (2c-b1) is preferably used. It is done.

(In the formula, X and Y may be the same or different and each represents an oxygen atom or a sulfur atom, and A ₁ , Ar ₅ , Ar ₆ , R _{2 to} R ₅ , R ₈ are represented by the general formula (2). Represents the meaning as shown.)

Ar ₇ in the general formula (3) includes a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, an acenaphthenyl group, a phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl group, and a triphenylenyl group. A phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are more preferable. Here, the phenyl group preferably has a substituted or unsubstituted condensed polycyclic aromatic group as a substituent, and is selected from a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluoranthenyl group, and triphenylenyl group. It is more preferable to have a substituent.
Ar ₈ in the general formula (3) is preferably a phenyl group having a substituent. In this case, examples of the substituent include an aromatic hydrocarbon group such as a phenyl group, a biphenylyl group, and a terphenyl group, a naphthyl group, and an anthracenyl group. Group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group and other condensed polycyclic aromatic groups are preferable, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, A pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are more preferable.
Ar ₉ in the general formula (3) is preferably a phenyl group having a substituent. In this case, examples of the substituent include aromatic hydrocarbon groups such as a phenyl group, a biphenylyl group, and a terphenyl group, a naphthyl group, and an anthracenyl group. Group, acenaphthenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group and other condensed polycyclic aromatic groups are preferable, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, A pyrenyl group, a fluoranthenyl group, and a triphenylenyl group are more preferable.
In the general formula (3), it is preferable from the viewpoint of thin film stability that Ar ₇ and Ar ₈ are not the same. Here, the case where Ar ₇ and Ar ₈ are not the same may be different substituents or different substitution positions.
In the general formula (3), Ar ₈ and Ar ₉ may be the same group, but may be easily crystallized by improving the symmetry of the whole molecule. From the viewpoint of thin film stability, Ar ₈ And Ar ₉ are preferably different groups, and Ar ₈ and Ar ₉ are not simultaneously hydrogen atoms.
In the general formula (3), it is preferable that one of Ar ₈ and Ar ₉ is a hydrogen atom.

Ar ₁₀ in the general formula (3) is preferably a triazinyl group, a pyridyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, an indolyl group, a quinoxalinyl group, a benzoimidazolyl group, a naphthyridinyl group, a phenanthrolinyl group, or an acridinyl group. A pyridyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, an indolyl group, a quinoxalinyl group, a benzimidazolyl group, a phenanthrolinyl group, and an acridinyl group are more preferable.
In the general formula (3), it is preferable from the viewpoint of the stability of the thin film that the bond position of Ar ₁₀ in the benzene ring is the meta position with respect to the bond position with the pyrimidine ring.

Examples of the compound having a pyrimidine ring structure represented by the general formula (3) include compounds having a pyrimidine ring structure represented by the following general formulas (3a) and (3b), which have different substituent bonding modes. .

(In formula, Ar < ₇ > -Ar < ₁₀ >, R < ₁₁ > -R < ₁₄ > represents the meaning as having shown in the said General formula (3).)

(In formula, Ar < ₇ > -Ar < ₁₀ >, R < ₁₁ > -R < ₁₄ > represents the meaning as having shown in the said General formula (3).)

Ar ₁₁ and Ar ₁₂ in the general formula (4) are phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthracenyl group, fluorenyl group, indenyl group, pyrenyl group, pyridyl group, carbazolyl group. Dibenzofuranyl group is preferable, and phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthracenyl group, and fluorenyl group are more preferable.
Examples of the substituent that they may have include a phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl group, a phenanthracenyl group, a fluorenyl group, a pyrenyl group, a pyridyl group, a triazinyl group, a pyrimidinyl group, and a quinolyl group. , Isoquinolyl group, indolyl group, carbazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, phenanthrolinyl group, acridinyl group are preferable, and phenyl group, naphthyl group, anthracenyl group, pyridyl group, quinolyl group, isoquinolyl group are more preferable. .

A ₂ in the general formula (4) is preferably a divalent group derived from benzene, biphenyl, naphthalene, anthracene, fluorene, phenanthrene, pyrene or pyridine, and a divalent group derived from benzene, naphthalene or pyridine. Groups are more preferred.

A ₃ in the general formula (4) is preferably a single bond or a divalent group derived from naphthalene, anthracene, fluorene, phenanthrene or pyrene, and a single bond or a divalent group derived from naphthalene or anthracene. More preferred.

B ₁ in the general formula (4) is preferably a pyridyl group, a bipyridyl group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group, an indolyl group, a carbolinyl group, a quinoxalinyl group, a benzimidazolyl group, a naphthyridinyl group, or a phenanthrolinyl group. A pyridyl group, a quinolyl group, and an isoquinolyl group are more preferable.

In General Formula (5), Ar ₁₃ is preferably a “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted condensed polycyclic aromatic group”, and includes a phenyl group, a biphenylyl group, a terphenylyl group, A naphthyl group, a phenanthracenyl group, an anthracenyl group, a fluorenyl group, a carbazolyl group, an indolyl group, a dibenzofuranyl group, and a dibenzothienyl group are more preferable.
In the general formula (5), Ar ₁₄ is preferably a “substituted or unsubstituted aromatic hydrocarbon group” or “substituted or unsubstituted condensed polycyclic aromatic group”, and includes a phenyl group, a biphenylyl group, a terphenylyl group, A naphthyl group, a phenanthracenyl group, an anthracenyl group, and a fluorenyl group are more preferable, and among them, a phenyl group, particularly an unsubstituted phenyl group is preferable.
As the arylamine compound represented by the general formula (5), an arylamine compound represented by the following general formula (5a) or the general formula (5b) is more preferably used.

（５ａ）

(5a)

(In the formula, Ar _{13 to} Ar ₁₅ represent the meanings as shown in the general formula (5), and Ar ₂₁ and Ar ₂₂ may be the same or different from each other, and are substituted or unsubstituted aromatic hydrocarbons. Represents a group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.)

（５ｂ）

(5b)

(In the formula, Ar ₁₃ and Ar ₁₄ represent the same meaning as shown in the general formula (5), and Ar _{21 to} Ar ₂₄ may be the same as or different from each other, and are substituted or unsubstituted aromatic hydrocarbons. Represents a group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.)

“Substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted” represented by Ar _{21 to} Ar ₂₄ in formula (5a) and formula (5b) Alternatively, the “aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “unsubstituted fused polycyclic aromatic group” may be Ar _1- in the general formula (1). “Aromatic carbonization” in “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” represented by Ar ₄ Examples thereof include those similar to those shown for “hydrogen group”, “aromatic heterocyclic group” or “fused polycyclic aromatic group”.
In addition, these groups may have a substituent, and as the substituent, a “substituted aromatic hydrocarbon group” represented by Ar _{1 to} Ar ₄ in the general formula (1), “substituted aromatic” The thing similar to what was shown regarding the "substituent" in a "heterocyclic group" or a "substituted condensed polycyclic aromatic group" can be mention | raise | lifted, and the aspect which can be taken can also mention the same thing.

In the general formula (5a), it is preferable that Ar ₁₃ and Ar ₂₁ are the same group, and Ar ₁₄ and Ar ₂₂ are the same group. In the general formula (5b), Ar ₁₃ , Ar ₂₁ and Ar ₂₃ are preferably the same group, and Ar ₁₄ , Ar ₂₂ and Ar ₂₄ are preferably the same group.

In the general formula (5), as the “substituent” in the “substituted aromatic hydrocarbon group”, “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar _{13 to} Ar ₁₆ , A deuterium atom, an optionally substituted linear or branched alkyl group having 1 to 6 carbon atoms, an optionally substituted linear group having 2 to 6 carbon atoms Or, a branched alkenyl group, a “substituted or unsubstituted aromatic hydrocarbon group” or a “substituted or unsubstituted condensed polycyclic aromatic group” is preferable, and a deuterium atom, phenyl group, biphenylyl group, naphthyl group, vinyl Groups are more preferred. It is also preferred that these groups are bonded to each other through a single bond to form a condensed aromatic ring.

Ar _{17 to} Ar ₂₀ in the general formula (6) are “substituted or unsubstituted aromatic hydrocarbon group”, “substituted or unsubstituted oxygen-containing aromatic heterocyclic group” or “substituted or unsubstituted condensation”. A “polycyclic aromatic group” is preferable, and a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthrenyl group, a fluorenyl group, and a dibenzofuranyl group are more preferable.
In the general formula (6), Ar ₁₇ and Ar ₁₈ or Ar ₁₉ and Ar ₂₀ are preferably different groups, and Ar ₁₇ and Ar ₁₈ and Ar ₁₉ and Ar ₂₀ are more preferably different groups.
In general formula (6), n1 is preferably 2 or 3.
As the bonding mode of the phenylene group in the general formula (6), all bonds are not 1,4-bonds but 1,2-bonds or 1,3-bonds from the viewpoint of the stability of the thin film that affects the device lifetime. It is preferable that a bond is mixed, and as a result, aryldiamine derivatives in which four (when n is 2), five (when n is 3) or six (when n is 4) phenylene groups are linked. 1,1 ′: 3 ′, 1 ″: 3 ″, 1 ′ ″-quarterphenyldiamine, 1,1 ′: 3 ′, 1 ″: 2 ″, 1 ′ ″: 3 ''',1''''-kinkphenyldiamine,1,1': 3 ', 1'':3'',1''': 3 ''',1''''-kinkphenyldiamine, 1,1 ′: 2 ′, 1 ″: 2 ″, 1 ′ ″-quarterphenyldiamine, 1,1 ′: 3 ′, 1 ″: 3 ″, 1 ′ ″-quarterphenyldiamine, 1, 1 ': 4', 1 ": 2", 1 ''' 4 ″ ′, 1 ″ ″-kinkphenyldiamine, 1,1 ′: 2 ′, 1 ″: 3 ″, 1 ′ ″: 2 ″ ′, 1 ″ ″-kinkphenyldiamine 1,1 ′: 4 ′, 1 ″: 3 ″, 1 ′ ″: 4 ′ ″, 1 ″ ″-kinkphenyldiamine, 1,1 ′: 2 ′, 1 ″: 2 '', 1 ''':2''', 1 ''''-kinkphenyldiamine and the like which are not linearly connected are preferable.

  The arylamine compound represented by the general formula (1), which is preferably used in the organic EL device of the present invention, is used as a constituent material of a hole injection layer, an electron blocking layer or a hole transport layer of the organic EL device. be able to. It is excellent in luminous efficiency and durability as compared with conventional materials, and is more preferably used as a material for a hole injection layer or a hole transport layer.

The amine derivative having a condensed ring structure represented by the general formula (2), which is preferably used in the organic EL device of the present invention, can be used as a constituent material of the light emitting layer of the organic EL device. It is excellent in luminous efficiency as compared with conventional materials and is a preferred compound as a dopant material for the light emitting layer.

The compound having a pyrimidine ring structure represented by the general formula (3) or the compound having a benzotriazole ring structure represented by the general formula (4), which is preferably used in the organic EL device of the present invention, is an organic EL. It can be used as a constituent material of the electron transport layer of the device.
The compound having a pyrimidine ring structure represented by the general formula (3) or the compound having a benzotriazole ring structure represented by the general formula (4) is excellent in electron injection and transport capability, and further has a stable thin film. It is a compound that is excellent in properties and durability and is preferred as a material for the electron transport layer.

  The arylamine compound represented by the general formula (5) or the general formula (6) that is preferably used in the organic EL device of the present invention can be used as a constituent material of the electron blocking layer of the organic EL device. It has a high electron blocking performance and is a preferred compound as a material for a layer adjacent to the anode side of the light emitting layer.

The organic EL device of the present invention is a material for an organic EL device excellent in hole and electron injection / transport performance, thin film stability and durability, and matches the characteristics of the material of the light emitting layer having a specific structure. Compared to conventional organic EL devices, the hole transport efficiency from the hole transport layer to the light-emitting layer is improved, and the electron transport efficiency from the electron transport layer to the light-emitting layer is also improved. As a result, the light emission efficiency is improved and the driving voltage is lowered, so that the durability of the organic EL element can be improved.
It has become possible to realize a long-life organic EL element with high luminous efficiency.

The organic EL device of the present invention is excellent in hole and electron injection / transport performance, thin film stability and durability, and has an arylamine compound having a specific structure capable of effectively expressing the role of hole injection / transport By selecting, holes can be efficiently injected and transported to the light emitting layer, and an organic EL element with high efficiency, low drive voltage, and long life can be realized. In addition, an arylamine compound having a specific structure is selected and combined with a specific electron transport material so as to achieve a carrier balance that matches the characteristics of the material of the light-emitting layer having the specific structure. In particular, a long-life organic EL element can be realized.
According to the present invention, the luminous efficiency and durability of a conventional organic EL device can be improved.

It is the figure which showed the organic EL element structure of Examples 9-13 and Comparative Examples 1-2.

Specific examples of preferable compounds among the arylamine compounds represented by the general formula (1) that are preferably used in the organic EL device of the present invention are shown below, but are not limited to these compounds. .

  Specific examples of preferable compounds among the amine derivatives having a condensed ring structure represented by the general formula (2), which are preferably used in the organic EL device of the present invention, are shown below, but are limited to these compounds. It is not something.

  In addition, the amine derivative which has the condensed ring structure mentioned above is compoundable according to a well-known method per se (for example, refer patent document 6).

Specific examples of preferable compounds among the compounds having a pyrimidine ring structure represented by the general formula (3), which are preferably used in the organic EL device of the present invention, are shown below. It is not limited to.

In addition, the compound which has the pyrimidine ring structure mentioned above is compoundable according to a method known per se (for example, refer to patent documents 6).

  Specific examples of preferable compounds among the compounds having a benzotriazole ring structure represented by the general formula (4), which are preferably used in the organic EL device of the present invention, are shown below. It is not limited to compounds.

（４−１）

(4-1)

（４−２）

(4-2)

（４−３）

(4-3)

（４−４）

(4-4)

（４−５）

(4-5)

（４−６）

(4-6)

（４−７）

(4-7)

（４−８）

(4-8)

（４−９）

(4-9)

（４−１０）

(4-10)

（４−１１）

(4-11)

（４−１２）

(4-12)

（４−１３）

(4-13)

（４−１４）

(4-14)

（４−１５）

(4-15)

（４−１６）

(4-16)

（４−１７）

(4-17)

（４−１８）

(4-18)

（４−１９）

(4-19)

（４−２０）

(4-20)

（４−２１）

(4-21)

（４−２２）

(4-22)

（４−２３）

(4-23)

（４−２４）

(4-24)

（４−２５）

(4-25)

（４−２６）

(4-26)

（４−２７）

(4-27)

（４−２８）

(4-28)

（４−２９）

(4-29)

（４−３０）

(4-30)

（４−３１）

(4-31)

（４−３２）

(4-32)

（４−３３）

(4-33)

（４−３４）

(4-34)

（４−３５）

(4-35)

（４−３６）

(4-36)

（４−３７）

(4-37)

（４−３８）

(4-38)

（４−３９）

(4-39)

（４−４０）

(4-40)

（４−４１）

(4-41)

（４−４２）

(4-42)

（４−４３）

(4-43)

（４−４４）

(4-44)

（４−４５）

(4-45)

（４−４６）

(4-46)

（４−４７）

(4-47)

（４−４８）

(4-48)

（４−４９）

(4-49)

（４−５０）

(4-50)

（４−５１）

(4-51)

（４−５２）

(4-52)

（４−５３）

(4-53)

（４−５４）

(4-54)

（４−５５）

(4-55)

（４−５６）

(4-56)

（４−５７）

(4-57)

（４−５８）

(4-58)

（４−５９）

(4-59)

（４−６０）

(4-60)

（４−６１）

(4-61)

（４−６２）

(4-62)

（４−６３）

(4-63)

（４−６４）

(4-64)

（４−６５）

(4-65)

（４−６６）

(4-66)

（４−６７）

(4-67)

（４−６８）

(4-68)

（４−６９）

(4-69)

（４−７０）

(4-70)

（４−７１）

(4-71)

（４−７２）

(4-72)

（４−７３）

(4-73)

（４−７４）

(4-74)

（４−７５）

(4-75)

（４−７６）

(4-76)

（４−７７）

(4-77)

（４−７８）

(4-78)

（４−７９）

(4-79)

（４−８０）

(4-80)

（４−８１）

(4-81)

（４−８２）

(4-82)

（４−８３）

(4-83)

（４−８４）

(4-84)

（４−８５）

(4-85)

（４−８６）

(4-86)

（４−８７）

(4-87)

（４−８８）

(4-88)

（４−８９）

(4-89)

（４−９０）

(4-90)

（４−９１）

(4-91)

（４−９２）

(4-92)

（４−９３）

(4-93)

（４−９４）

(4-94)

（４−９５）

(4-95)

（４−９６）

(4-96)

（４−９７）

(4-97)

（４−９８）

(4-98)

（４−９９）

(4-99)

（４−１００）

(4-100)

（４−１０１）

(4-101)

（４−１０２）

(4-102)

（４−１０３）

(4-103)

（４−１０４）

(4-104)

（４−１０５）

(4-105)

（４−１０６）

(4-106)

（４−１０７）

(4-107)

（４−１０８）

(4-108)

（４−１０９）

(4-109)

（４−１１０）

(4-110)

（４−１１１）

(4-111)

（４−１１２）

(4-112)

（４−１１３）

(4-113)

（４−１１４）

(4-114)

（４−１１５）

(4-115)

（４−１１６）

(4-116)

（４−１１７）

(4-117)

（４−１１８）

(4-118)

（４−１１９）

(4-119)

（４−１２０）

(4-120)

（４−１２１）

(4-121)

（４−１２２）

(4-122)

（４−１２３）

(4-123)

（４−１２４）

(4-124)

（４−１２５）

(4-125)

（４−１２６）

(4-126)

（４−１２７）

(4-127)

（４−１２８）

(4-128)

（４−１２９）

(4-129)

（４−１３０）

(4-130)

（４−１３１）

(4-131)

（４−１３２）

(4-132)

（４−１３３）

(4-133)

（４−１３４）

(4-134)

（４−１３５）

(4-135)

（４−１３６）

(4-136)

（４−１３７）

(4-137)

（４−１３８）

(4-138)

（４−１３９）

(4-139)

（４−１４０）

(4-140)

（４−１４１）

(4-141)

（４−１４２）

(4-142)

（４−１４３）

(4-143)

（４−１４４）

(4-144)

（４−１４５）

(4-145)

（４−１４６）

(4-146)

（４−１４７）

(4-147)

（４−１４８）

(4-148)

（４−１４９）

(4-149)

（４−１５０）

(4-150)

（４−１５１）

(4-151)

（４−１５２）

(4-152)

（４−１５３）

(4-153)

（４−１５４）

(4-154)

（４−１５５）

(4-155)

（４−１５６）

(4-156)

（４−１５７）

(4-157)

（４−１５８）

(4-158)

（４−１５９）

(4-159)

（４−１６０）

(4-160)

（４−１６１）

(4-161)

（４−１６２）

(4-162)

（４−１６３）

(4-163)

（４−１６４）

(4-164)

（４−１６５）

(4-165)

（４−１６６）

(4-166)

（４−１６７）

(4-167)

（４−１６８）

(4-168)

（４−１６９）

(4-169)

（４−１７０）

(4-170)

（４−１７１）

(4-171)

（４−１７２）

(4-172)

（４−１７３）

(4-173)

（４−１７４）

(4-174)

In addition, the compound which has the benzotriazole ring structure mentioned above is compoundable according to a method known per se (for example, refer to patent documents 7).

  Specific examples of preferable compounds among the arylamine compounds represented by the general formula (5) that are preferably used in the organic EL device of the present invention are shown below, but are not limited to these compounds. .

（５−１）

(5-1)

（５−２）

(5-2)

（５−３）

(5-3)

（５−４）

(5-4)

（５−５）

(5-5)

（５−６）

(5-6)

（５−７）

(5-7)

（５−８）

(5-8)

（５−９）

(5-9)

（５−１０）

(5-10)

（５−１１）

(5-11)

（５−１２）

(5-12)

（５−１３）

(5-13)

（５−１４）

(5-14)

（５−１５）

(5-15)

（５−１６）

(5-16)

（５−１７）

(5-17)

（５−１８）

(5-18)

（５−１９）

(5-19)

（５−２０）

(5-20)

（５−２１）

(5-21)

（５−２２）

(5-22)

（５−２３）

(5-23)

（５−２４）

(5-24)

（５−２５）

(5-25)

（５−２６）

(5-26)

（５−２７）

(5-27)

（５−２８）

(5-28)

（５−２９）

(5-29)

（５−３０）

(5-30)

（５−３１）

(5-31)

（５−３２）

(5-32)

（５−３３）

(5-33)

（５−３４）

(5-34)

（５−３５）

(5-35)

（５−３６）

(5-36)

（５−３７）

(5-37)

（５−３８）

(5-38)

（５−３９）

(5-39)

（５−４０）

(5-40)

（５−４１）

(5-41)

（５−４２）

(5-42)

（５−４３）

(5-43)

（５−４４）

(5-44)

（５−４５）

(5-45)

（５−４６）

(5-46)

（５−４７）

(5-47)

（５−４８）

(5-48)

（５−４９）

(5-49)

（５−５０）

(5-50)

（５−５１）

(5-51)

（５−５２）

(5-52)

（５−５３）

(5-53)

（５−５４）

(5-54)

（５−５５）

(5-55)

（５−５６）

(5-56)

（５−５７）

(5-57)

（５−５８）

(5-58)

（５−５９）

(5-59)

（５−６０）

(5-60)

（５−６１）

(5-61)

（５−６２）

(5-62)

（５−６３）

(5-63)

（５−６４）

(5-64)

（５−６５）

(5-65)

（５−６６）

(5-66)

（５−６７）

(5-67)

（５−６８）

(5-68)

（５−６９）

(5-69)

（５−７０）

(5-70)

（５−７１）

(5-71)

（５−７２）

(5-72)

（５−７３）

(5-73)

（５−７４）

(5-74)

（５−７５）

(5-75)

（５−７６）

(5-76)

（５−７７）

(5-77)

（５−７８）

(5-78)

（５−７９）

(5-79)

（５−８０）

(5-80)

（５−８１）

(5-81)

（５−８２）

(5-82)

（５−８３）

(5-83)

（５−８４）

(5-84)

（５−８５）

(5-85)

（５−８６）

(5-86)

（５−８７）

(5-87)

（５−８８）

(5-88)

（５−８９）

(5-89)

（５−９０）

(5-90)

（５−９１）

(5-91)

（５−９２）

(5-92)

（５−９３）

(5-93)

（５−９４）

(5-94)

（５−９５）

(5-95)

（５−９６）

(5-96)

（５−９７）

(5-97)

（５−９８）

(5-98)

（５−９９）

(5-99)

（５−１００）

(5-100)

（５−１０１）

(5-101)

（５−１０２）

(5-102)

（５−１０３）

(5-103)

（５−１０４）

(5-104)

（５−１０５）

(5-105)

（５−１０６）

(5-106)

（５−１０７）

(5-107)

（５−１０８）

(5-108)

（５−１０９）

(5-109)

（５−１１０）

(5-110)

（５−１１１）

(5-111)

（５−１１２）

(5-112)

（５−１１３）

(5-113)

（５−１１４）

(5-114)

（５−１１５）

(5-115)

（５−１１６）

(5-116)

（５−１１７）

(5-117)

（５−１１８）

(5-118)

（５−１１９）

(5-119)

（５−１２０）

(5-120)

（５−１２１）

(5-121)

（５−１２２）

(5-122)

（５−１２３）

(5-123)

（５−１２４）

(5-124)

（５−１２５）

(5-125)

（５−１２６）

(5-126)

（５−１２７）

(5-127)

（５−１２８）

(5-128)

（５−１２９）

(5-129)

（５−１３０）

(5-130)

（５−１３１）

(5-131)

（５−１３２）

(5-132)

（５−１３３）

(5-133)

（５−１３４）

(5-134)

（５−１３５）

(5-135)

（５−１３６）

(5-136)

（５−１３７）

(5-137)

（５−１３８）

(5-138)

（５−１３９）

(5-139)

（５−１４０）

(5-140)

（５−１４１）

(5-141)

（５−１４２）

(5-142)

（５−１４３）

(5-143)

（５−１４４）

(5-144)

（５−１４５）

(5-145)

（５−１４６）

(5-146)

（５−１４７）

(5-147)

（５−１４８）

(5-148)

（５−１４９）

(5-149)

（５−１５０）

(5-150)

（５−１５１）

(5-151)

（５−１５２）

(5-152)

（５−１５３）

(5-153)

（５−１５４）

(5-154)

（５−１５５）

(5-155)

（５−１５６）

(5-156)

（５−１５７）

(5-157)

（５−１５８）

(5-158)

（５−１５９）

(5-159)

（５−１６０）

(5-160)

（５−１６１）

(5-161)

（５−１６２）

(5-162)

（５−１６３）

(5-163)

（５−１６４）

(5-164)

（５−１６５）

(5-165)

（５−１６６）

(5-166)

（５−１６７）

(5-167)

（５−１６８）

(5-168)

（５−１６９）

(5-169)

（５−１７０）

(5-170)

（５−１７１）

(5-171)

（５−１７２）

(5-172)

（５−１７３）

(5-173)

（５−１７４）

(5-174)

（５−１７５）

(5-175)

（５−１７６）

(5-176)

（５−１７７）

(5-177)

（５−１７８）

(5-178)

（５−１７９）

(5-179)

（５−１８０）

(5-180)

（５−１８１）

(5-181)

（５−１８２）

(5-182)

（５−１８３）

(5-183)

（５−１８４）

(5-184)

（５−１８５）

(5-185)

（５−１８６）

(5-186)

（５−１８７）

(5-187)

（５−１８８）

(5-188)

（５−１８９）

(5-189)

（５−１９０）

(5-190)

（５−１９１）

(5-191)

（５−１９２）

(5-192)

（５−１９３）

(5-193)

（５−１９４）

(5-194)

（５−１９５）

(5-195)

（５−１９６）

(5-196)

（５−１９７）

(5-197)

（５−１９８）

(5-198)

（５−１９９）

(5-199)

（５−２００）

(5-200)

（５−２０１）

(5-201)

（５−２０２）

(5-202)

（５−２０３）

(5-203)

（５−２０４）

(5-204)

（５−２０５）

(5-205)

（５−２０６）

(5-206)

（５−２０７）

(5-207)

（５−２０８）

(5-208)

（５−２０９）

(5-209)

（５−２１０）

(5-210)

（５−２１１）

(5-211)

（５−２１２）

(5-212)

（５−２１３）

(5-213)

（５−２１４）

(5-214)

（５−２１５）

(5-215)

（５−２１６）

(5-216)

（５−２１７）

(5-217)

  Specific examples of preferable compounds among the arylamine compounds represented by the general formula (6) that are preferably used in the organic EL device of the present invention are shown below, but are not limited to these compounds. .

（６−１）

(6-1)

（６−２）

(6-2)

（６−３）

(6-3)

（６−４）

(6-4)

（６−５）

(6-5)

（６−６）

(6-6)

（６−７）

(6-7)

（６−８）

(6-8)

（６−９）

(6-9)

（６−１０）

(6-10)

（６−１１）

(6-11)

（６−１２）

(6-12)

（６−１３）

(6-13)

（６−１４）

(6-14)

（６−１５）

(6-15)

（６−１６）

(6-16)

（６−１７）

(6-17)

（６−１８）

(6-18)

（６−１９）

(6-19)

（６−２０）

(6-20)

（６−２１）

(6-21)

（６−２２）

(6-22)

（６−２３）

(6-23)

（６−２４）

(6-24)

（６−２５）

(6-25)

（６−２６）

(6-26)

（６−２７）

(6-27)

（６−２８）

(6-28)

（６−２９）

(6-29)

（６−３０）

(6-30)

（６−３１）

(6-31)

（６−３２）

(6-32)

（６−３３）

(6-33)

（６−３４）

(6-34)

（６−３５）

(6-35)

（６−３６）

(6-36)

（６−３７）

(6-37)

（６−３８）

(6-38)

The arylamine compound represented by the general formula (1) was purified by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization or crystallization using a solvent, sublimation purification, and the like. The compound was identified by NMR analysis. As physical property values, melting point, glass transition point (Tg) and work function were measured. The melting point is an index of vapor deposition, the glass transition point (Tg) is an index of stability in a thin film state, and the work function is an index of hole transportability and hole blocking property.
In addition, the compound used in the organic EL device of the present invention is purified by column chromatography, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization using a solvent, crystallization method, sublimation purification method, etc. Finally, the product purified by the sublimation purification method was used.

  Melting | fusing point and glass transition point (Tg) were measured with the highly sensitive differential scanning calorimeter (The Bruker AXS make, DSC3100SA) using powder.

The work function was determined using an ionization potential measuring apparatus (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) after forming a 100 nm thin film on the ITO substrate.

As the structure of the organic EL device of the present invention, the substrate is composed of an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode sequentially on the substrate, and the hole transport layer and the light emitting layer. And those having a hole blocking layer between the light emitting layer and the electron transport layer, and those having an electron injection layer between the electron transport layer and the cathode. In these multilayer structures, it is possible to omit or double several organic layers. For example, a structure that serves as a hole injection layer and a hole transport layer, and a structure that serves as an electron injection layer and an electron transport layer. And so on. In addition, it is possible to have a structure in which two or more organic layers having the same function are stacked, a structure in which two hole transport layers are stacked, a structure in which two light emitting layers are stacked, and two electron transport layers. A stacked configuration is also possible. As the structure of the organic EL device of the present invention, a structure having an electron blocking layer between the hole transport layer and the light emitting layer is preferable.

As the hole injection layer of the organic EL device of the present invention, a material obtained by P-doping an electron acceptor with respect to the arylamine compound represented by the general formula (1) is preferably used. Examples of the electron acceptor include trisbromophenylamine hexachloroantimony, tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4TCNQ), and a radicalene derivative (for example, Patent Document 8) is preferable, and a radiolene derivative is more preferable. Further, as the hole injection layer of the organic EL device of the present invention, in addition to the arylamine compound represented by the general formula (1), a starburst type triphenylamine derivative, various triphenylamine tetramers, and the like Materials: Porphyrin compounds typified by copper phthalocyanine; acceptor heterocyclic compounds such as hexacyanoazatriphenylene, coating-type polymer materials, and the like can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.

As the hole transport layer of the organic EL device of the present invention, the arylamine compound represented by the general formula (1) is used. These may be formed alone, or may be used as a single layer formed by mixing with other hole transport materials, or the layers formed independently may be mixed to form a film. Alternatively, a layered structure of layers formed by mixing with each other or a layer formed by mixing alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
As a hole transporting material that can be mixed or used simultaneously with the arylamine compound represented by the general formula (1), N, N′-diphenyl-N, N′-di (m-tolyl) benzidine (TPD) is used. ), N, N′-diphenyl-N, N′-di (α-naphthyl) benzidine (NPD), benzidine derivatives such as N, N, N ′, N′-tetrabiphenylylbenzidine, 1,1-bis [ 4- (di-4-tolylamino) phenyl] cyclohexane (TAPC), a triphenylamine derivative having two triphenylamine skeletons as a whole molecule, a triphenylamine skeleton having four triphenylamine skeletons as a whole molecule Examples thereof include a phenylamine derivative and a triphenylamine derivative having three triphenylamine skeletons as a whole molecule.

As an electron blocking layer of the organic EL device of the present invention, in addition to the arylamine compound represented by the general formula (5) or (6), 4,4 ′, 4 ″ -tri (N-carbazolyl) triphenylamine (TCTA), 9,9-bis [4- (carbazol-9-yl) phenyl] fluorene, 1,3-bis (carbazol-9-yl) benzene (mCP), 2,2-bis (4-carbazole- Represented by carbazole derivatives such as 9-ylphenyl) adamantane (Ad-Cz), 9- [4- (carbazol-9-yl) phenyl] -9- [4- (triphenylsilyl) phenyl] -9H-fluorene A compound having an electron blocking action such as a compound having a triphenylsilyl group and a triarylamine structure can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to the vapor deposition method.

As the light emitting layer of the organic EL device of the present invention, an amine derivative having a condensed ring structure represented by the general formula (2) is used. As the light emitting material that can be mixed or used together with the amine derivative represented by the general formula (2), various metal complexes such as metal complexes of quinolinol derivatives including Alq ₃ , anthracene derivatives, bisstyrylbenzene derivatives, Examples thereof include oxazole derivatives and polyparaphenylene vinylene derivatives.
In addition, the light-emitting layer may be composed of a host material and a dopant material, and in addition to the light-emitting material, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or the like can be used as the host material. As the dopant material, an amine derivative having a condensed ring structure represented by the general formula (2) is used, and as a material that can be mixed or used simultaneously, quinacridone, coumarin, rubrene, perylene, and derivatives thereof, benzopyran Derivatives, indenophenanthrene derivatives, rhodamine derivatives, aminostyryl derivatives and the like can be mentioned. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
As the light emitting layer of the organic EL device of the present invention, an amine derivative having a condensed ring structure represented by the general formula (2) is preferably used as a dopant material.

It is also possible to use a phosphorescent emitter as the light emitting material. As the phosphorescent emitter, a phosphorescent emitter of a metal complex such as iridium or platinum can be used. Green phosphorescent emitters such as Ir (ppy) ₃ , blue phosphorescent emitters such as FIrpic and FIr6, red phosphorescent emitters such as Btp ₂ Ir (acac), and the like are used as host materials. As the hole injecting / transporting host material, carbazole derivatives such as 4,4′-di (N-carbazolyl) biphenyl (CBP), TCTA, and mCP can be used. As an electron transporting host material, p-bis (triphenylsilyl) benzene (UGH2) or 2,2 ′, 2 ″-(1,3,4-phenylene) -tris (1-phenyl-1H-benzimidazole) ) (TPBI) or the like, and a high-performance organic EL element can be manufactured.

In order to avoid concentration quenching, the host material of the phosphorescent light emitting material is preferably doped by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light emitting layer.

In addition, a material that emits delayed fluorescence such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN can be used as the light-emitting material. (For example, see Non-Patent Document 3)

These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.

As a hole blocking layer of the organic EL device of the present invention, a phenanthroline derivative such as bathocuproine (BCP) or aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter abbreviated as BAlq). In addition to metal complexes of quinolinol derivatives such as), compounds having a hole blocking action such as various rare earth complexes, triazole derivatives, triazine derivatives, and oxadiazole derivatives can be used. These materials may also serve as the material for the electron transport layer. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.

As the electron transport layer of the organic EL device of the present invention, a compound having a pyrimidine ring structure represented by the general formula (3) or a compound having a benzotriazole ring structure represented by the following general formula (4) is preferably used. . These may be formed alone, or may be used as a single layer formed by mixing with other electron transporting materials, or the layers formed independently may be mixed to form a film. A layered structure of layers formed by mixing layers with each other or a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
As an electron transporting material that can be mixed or used simultaneously with the compound having a pyrimidine ring structure represented by the general formula (3) or the compound having a benzotriazole ring structure represented by the following general formula (4), Metal complexes of quinolinol derivatives such as Alq ₃ and BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benzimidazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives And pyridoindole derivatives, phenanthroline derivatives, silole derivatives and the like.

As the electron injection layer of the organic EL device of the present invention, an alkali metal salt such as lithium fluoride and cesium fluoride, an alkaline earth metal salt such as magnesium fluoride, and a metal oxide such as aluminum oxide can be used. In the preferred selection of the electron transport layer and the cathode, this can be omitted.

As the cathode of the organic EL device of the present invention, an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.

Embodiments of the present invention will be specifically described below with reference to examples. However, the present invention is not limited to the following examples.

<Synthesis of N, N, N ′, N′-tetrakis-biphenyl-4-yl- (2-phenyl) -benzene-1,4-diamine (Compound 1-1)>
Under nitrogen atmosphere, bis-biphenyl-4-yl- (6-bromobiphenyl-3-yl) -amine: 10.0 g, bis-biphenyl-4-yl-amine: 7.0 g, t-butoxy sodium: 2. 6 g of toluene: 100 ml was added to the reaction vessel, followed by addition of toluene solution of t-butylphosphine (50 wt%): 0.9 g, palladium (II): 0.2 g and heating, followed by heating under reflux. Stir for hours. Silica gel: 28.0 g was added to the reaction solution and subjected to adsorption purification, followed by filtration and concentration under reduced pressure to obtain a crude product. The crude product is purified by crystallization with a toluene / n-heptane solvent, whereby N, N, N ′, N′-tetrakis-biphenyl-4-yl- (2-phenyl) -benzene-1,4-diamine ( 10.4 g (yield: 72.5%) of a white powder of compound 1-1) was obtained.

The structure of the obtained white powder was identified using NMR.
^The following 44 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ).
δ (ppm) = 7.67 (8H), 7.54 (4H), 7.50-7.39 (12H), 7.36-7.22 (9H), 7.20-7.07 (7H) ), 6.95 (4H).

<Synthesis of N, N, N'-Tris-biphenyl-4-yl-N'-phenyl- (3-phenyl) -benzene-1,4-diamine (Compound 1-7)>
Under nitrogen atmosphere, bis-biphenyl-4-yl- (6-bromobiphenyl-3-yl) -amine: 12.0 g, biphenyl-4-yl-phenyl-amine: 6.4 g, t-butoxy sodium: 3. 1 g of toluene: 120 ml was added to the reaction vessel, followed by the addition of toluene solution of t-butylphosphine (50 wt%): 1.0 g and palladium (II) acetate: 0.2 g and heating. Stir for hours. The reaction solution was filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified using column chromatography (carrier: silica gel, eluent: toluene / n-heptane), and then subjected to crystallization purification using a mixed solvent of toluene / methanol, so that N, N, N ′ -Tris-biphenyl-4-yl-N'-phenyl- (2-phenyl) -benzene-1,4-diamine (compound 1-7) white powder: 12.5 g (yield: 80.3%) Got.

The structure of the obtained white powder was identified using NMR.
^The following 40 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ).
δ (ppm) = 7.68 (4H), 7.65 (4H), 7.57 (2H), 7.49-7.38 (8H), 7.35-7.10 (16H), 7. 05 (1H), 6.93-6.83 (5H).

<N, N-bis-biphenyl-4-yl-N ′-(9,9-dimethyl-9H-fluoren-2-yl) -N′-phenyl- (3-phenyl) -benzene-1,4-diamine Synthesis of (Compound 1-9)>
Under a nitrogen atmosphere, bis-biphenyl-4-yl- (6-bromobiphenyl-3-yl) -amine: 12.0 g, 9,9-dimethyl-9H-fluoren-2-yl-phenyl-amine: 7.4 g , T-butoxy sodium: 3.1 g, toluene: 120 ml were added to the reaction vessel, followed by addition of t-butylphosphine in toluene solution (50 wt%): 1.0 g, palladium acetate (II): 0.2 g. Heat and stir at reflux for 16 hours. The reaction solution was filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified using column chromatography (carrier: silica gel, eluent: toluene / n-heptane), and then subjected to crystallization purification using a mixed solvent of toluene / methanol, whereby N, N-bis- Of biphenyl-4-yl-N ′-(9,9-dimethyl-9H-fluoren-2-yl) -N′-phenyl- (3-phenyl) -benzene-1,4-diamine (compound 1-9) White powder: 14.2 g (yield: 86.4%) was obtained.

The structure of the obtained white powder was identified using NMR.
^The following 44 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ).
δ (ppm) = 7.68 (4H), 7.66 (4H), 7.62 (1H), 7.54-7.42 (6H), 7.36-7.03 (18H), 6. 96-6.83 (4H), 6.73 (1H), 1.25 (6H).

<N, N′-bis-biphenyl-4-yl-N- (9,9-dimethyl-9H-fluoren-2-yl) -N′-phenyl- (3-phenyl) -benzene-1,4-diamine Synthesis of (Compound 1-12)>
Under a nitrogen atmosphere, biphenyl-4-yl- (6-bromobiphenyl-3-yl)-(9,9-dimethyl-9H-fluoren-2-yl) -amine: 12.0 g, biphenyl-4-yl-phenyl -Amine: 6.0 g, t-butoxy sodium: 2.9 g, toluene: 120 ml were added to the reaction vessel, followed by t-butylphosphine in toluene (50 wt%): 1.0 g, palladium (II) acetate: 0.2g was added and it heated, and it stirred under recirculation | reflux for 3 hours. The reaction solution was filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified using column chromatography (carrier: silica gel, eluent: toluene / n-heptane), followed by crystallization purification using a mixed solvent of tetrahydrofuran / methanol to obtain N, N′-bis. -Biphenyl-4-yl-N- (9,9-dimethyl-9H-fluoren-2-yl) -N'-phenyl- (3-phenyl) -benzene-1,4-diamine (compound 1-12) A pale yellow powder: 10.9 g (yield: 71.1%) was obtained.

The structure of the obtained pale yellow powder was identified using NMR.
^The following 44 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ).
δ (ppm) = 7.80 (1H), 7.75 (1H), 7.66 (4H), 7.59-7.38 (10H), 7.35-7.23 (7H), 7. 17-7.09 (9H), 7.02 (1H), 6.92 (2H), 6.87-6.82 (3H), 1.40 (6H).

<N-biphenyl-4-yl-N, N′-bis (9,9-dimethyl-9H-fluoren-2-yl) -N′-phenyl- (3-phenyl) -benzene-1,4-diamine ( Synthesis of Compound 1-13)>
Under a nitrogen atmosphere, biphenyl-4-yl- (6-bromobiphenyl-3-yl)-(9,9-dimethyl-9H-fluoren-2-yl) -amine: 12.0 g, 9,9-dimethyl-9H -Fluoren-2-yl-phenyl-amine: 6.9 g, t-butoxy sodium: 2.9 g, toluene: 120 ml are added to the reaction vessel, followed by t-butylphosphine in toluene (50 wt%): 1. 0 g and palladium (II) acetate: 0.2 g were added and heated, followed by stirring for 9 hours under reflux. The reaction solution was filtered and concentrated under reduced pressure to obtain a crude product. The crude product was purified using column chromatography (carrier: silica gel, eluent: toluene / n-heptane), and then subjected to crystallization purification using a mixed solvent of tetrahydrofuran / methanol, whereby N-biphenyl-4- White of yl-N, N′-bis (9,9-dimethyl-9H-fluoren-2-yl) -N′-phenyl- (3-phenyl) -benzene-1,4-diamine (Compound 1-13) 11.3 g (yield: 70.0%) of powder was obtained.

The structure of the obtained white powder was identified using NMR.
^The following 48 hydrogen signals were detected by ¹ H-NMR (DMSO-d ₆ ).
δ (ppm) = 7.79 (1H), 7.75 (1H), 7.69-7.61 (5H), 7.54-7.41 (6H), 7.35-6.95 (20H) ), 6.88 (1H), 6.82 (1H), 6.74 (1H), 1.41 (6H), 1.26 (6H).

About the arylamine compound represented by General formula (1), melting | fusing point and glass transition point were measured with the highly sensitive differential scanning calorimeter (The product made by Bruker AXS, DSC3100SA).
Melting point Glass transition point
Compound of Example 1 Not observed 120 ° C.
Compound of Example 2 Not observed 104 ° C.
Compound of Example 3 248 ° C. 116 ° C.
Compound of Example 4 not observed 115 ° C.
Compound of Example 5 Not observed 122 ° C

The arylamine compound represented by the general formula (1) has a glass transition point of 100 ° C. or higher, which indicates that the thin film state is stable.

Using the arylamine compound represented by the general formula (1), a vapor deposition film having a film thickness of 100 nm is prepared on the ITO substrate, and an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) is used. The work function was measured.
Work Function Compound of Example 1 5.53 eV
Compound of Example 2 5.55 eV
Compound of Example 3 5.50 eV
Compound of Example 4 5.49 eV
Compound of Example 5 5.45 eV

The arylamine compound represented by the general formula (1) exhibits a suitable energy level as compared with a work function of 5.4 eV possessed by a general hole transport material such as NPD or TPD. It can be seen that it has a hole transport capability.

As shown in FIG. 1, the organic EL element has a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2. 6, an electron transport layer 7, an electron injection layer 8, and a cathode (aluminum electrode) 9 were deposited in this order.

Specifically, the glass substrate 1 formed with ITO having a thickness of 150 nm was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 200 ° C. for 10 minutes. Then, after performing UV ozone treatment for 15 minutes, this glass substrate with ITO was attached in a vacuum evaporation machine, and pressure was reduced to 0.001 Pa or less. Subsequently, as a hole injection layer 3 so as to cover the transparent anode 2, an electron acceptor (Acceptor-1) having the following structural formula and the compound (1-1) of Example 1 were deposited at an evaporation rate ratio of Acceptor-1: Compound. Binary vapor deposition was performed at a vapor deposition rate of (1-1) = 3: 97 to form a film thickness of 5 nm. On the hole injection layer 3, the compound (1-1) of Example 1 was formed as a hole transport layer 4 so as to have a film thickness of 40 nm. On the hole transport layer 4, a compound (6-11) having the following structural formula was formed as the electron blocking layer 5 so as to have a film thickness of 10 nm. On this electron blocking layer 5, as the light emitting layer 6, a compound (2-1) having the following structural formula and a compound EMH-1 having the following structural formula are deposited with an evaporation rate ratio of EMD-1: EMH-1 = 5: 95. Binary vapor deposition was performed at a vapor deposition rate of 20 nm. On this light emitting layer 6, as the electron transport layer 7, the compound (3-125) of the following structural formula and the compound (ETM-1) of the following structural formula are deposited at a deposition rate ratio of 3-125: ETM-1 = 50: Binary vapor deposition was performed at a vapor deposition rate of 50 to form a film thickness of 30 nm. On the electron transport layer 7, lithium fluoride was formed as the electron injection layer 8 to a thickness of 1 nm. Finally, aluminum was deposited to 100 nm to form the cathode 9. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.

In Example 9, the same conditions except that the compound (1-7) of Example 2 was used instead of the compound (1-1) of Example 1 as the material of the hole injection layer 3 and the hole transport layer 4 Thus, an organic EL element was produced. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.

In Example 9, the same conditions except that the compound (1-9) of Example 3 was used in place of the compound (1-1) of Example 1 as the material of the hole injection layer 3 and the hole transport layer 4 Thus, an organic EL element was produced. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.

In Example 9, the same conditions except that the compound (1-12) of Example 4 was used in place of the compound (1-1) of Example 1 as the material of the hole injection layer 3 and the hole transport layer 4. Thus, an organic EL element was produced. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.

In Example 9, the same conditions except that the compound (1-13) of Example 5 was used instead of the compound (1-1) of Example 1 as the material of the hole injection layer 3 and the hole transport layer 4. Thus, an organic EL element was produced. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.

[Comparative Example 1]
For comparison, in Example 9, except that HTM-1 having the following structural formula was used instead of the compound (1-1) of Example 1 as the material of the hole injection layer 3 and the hole transport layer 4. The organic EL element was produced under the conditions described above. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.

[Comparative Example 2]
For comparison, in Example 9, except that HTM-2 having the following structural formula was used instead of the compound (1-1) of Example 1 as the material of the hole injection layer 3 and the hole transport layer 4. The organic EL element was produced under the conditions described above. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air | atmosphere. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage was applied to the produced organic EL element.

The results of measuring the element lifetime using the organic EL elements prepared in Examples 9 to 13 and Comparative Examples 1 and 2 are summarized in Table 1. The element lifetime corresponds to 95% of the emission brightness of 1900 cd / m ² (when the initial brightness is 100%) when the constant current drive is performed with the emission brightness (initial brightness) at the start of light emission being 2000 cd / m ² : It was measured as the time to decay to 95% decay.

As shown in Table 1, the luminous efficiency when a current density of 10 mA / cm ² was passed was 8-9 to 8.27 cd / A of the organic EL elements of Comparative Examples 1 and 2, and Examples 9 to In the 13 organic EL elements, the efficiency was as high as 8.99 to 9.11 cd / A. In addition, in terms of power efficiency, the organic EL elements of Examples 9 to 13 are as high as 7.15 to 7.26 lm / W, compared to 6.64 to 6.72 lm / W of the organic EL elements of Comparative Examples 1 and 2. It was efficiency. Furthermore, in the element lifetime (95% attenuation), the organic EL elements of Examples 9 to 13 have a longer lifetime of 271 to 297 hours compared to 147 to 254 hours of the organic EL elements of Comparative Examples 1 and 2. I understand.

The organic EL device of the present invention has a carrier balance inside the organic EL device by combining an arylamine compound having a specific structure and an amine derivative having a specific condensed ring structure (and a compound having a specific pyrimidine ring structure). Improved and combined with a carrier balance that matches the characteristics of the light-emitting material, it is possible to realize an organic EL element with higher luminous efficiency and longer life than conventional organic EL elements. all right.

  The organic EL device of the present invention, which combines an arylamine compound having a specific structure and an amine derivative having a specific condensed ring structure (and a compound having a specific pyrimidine ring structure), has improved luminous efficiency and organic EL. The durability of the element can be improved. For example, it can be applied to household appliances and lighting applications.

DESCRIPTION OF SYMBOLS 1 Glass substrate 2 Transparent anode 3 Hole injection layer 4 Hole transport layer 5 Electron blocking layer 6 Light emitting layer 7 Electron transport layer 8 Electron injection layer 9 Cathode

Claims (4)

In the organic electroluminescence device having at least an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole transport layer contains an arylamine compound represented by the following general formula (1), and The said light emitting layer contains the amine derivative which has a condensed ring structure represented by following General formula (2), The organic electroluminescent element characterized by the above-mentioned.

(1)
(In the formula, Ar _{1 to} Ar ₄ may be the same as or different from each other, and are a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic ring. R ₁ represents a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent. A cycloalkyl group having 5 to 10 carbon atoms which may have a substituent, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a substituent. A linear or branched alkyloxy group having 1 to 6 carbon atoms which may have, a cycloalkyloxy group having 5 to 10 carbon atoms which may have a substituent, substituted or unsubstituted Aromatic hydrocarbon group, A substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, r ₁ represents an integer of ₁ to 4, and r ₁ is 2. In the case where it is an integer of ˜4, a plurality of R ₁ bonded to the same benzene ring may be the same or different from each other, and bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. Where Ar ₁ and Ar ₂ , Ar ₃ and Ar ₄ may be bonded to each other through a single bond or a substituted or unsubstituted methylene group, oxygen atom, or sulfur atom. A ring may be formed.)

(In the formula, A ₁ is a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, Or represents a single bond, and Ar ₅ and Ar ₆ may be the same or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted condensed groups A polycyclic aromatic group which may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring, and R _{2 to} R ₅ may be the same as each other. May be different, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, Optionally substituted 5 carbon atoms Or a cycloalkyl group having 10 carbon atoms, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a straight chain having 1 to 6 carbon atoms which may have a substituent. A linear or branched alkyloxy group, an optionally substituted cycloalkyloxy group having 5 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic complex; Substituted with a group selected from a cyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, a substituted or unsubstituted aryloxy group, an aromatic hydrocarbon group, an aromatic heterocyclic group or a condensed polycyclic aromatic group A di-substituted amino group, each group may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring, R ₂ to In the benzene ring to which R ₅ is bonded, any one group of R _{2 to} R ₅ is removed, and the removed part and other groups of R _{2 to} R ₅ are substituted or unsubstituted methylene groups, oxygen A ring may be bonded to each other via an atom, a sulfur atom, or a monosubstituted amino group, and R _{6 to} R ₈ may be the same or different from each other, and may be a hydrogen atom, a deuterium atom, a fluorine atom, A chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, and a carbon atom having 5 to 10 carbon atoms which may have a substituent A cycloalkyl group, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, and a linear chain having 1 to 6 carbon atoms which may have a substituent Or branched alkyloxy group, substituted A cycloalkyloxy group having 5 to 10 carbon atoms which may have a group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycycle An aromatic group, or a substituted or unsubstituted aryloxy group, each group being bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring Alternatively, in the benzene ring to which R _{6 to} R ₈ are bonded, any one group of R _{6 to} R ₈ is removed, and the removed part and the other group of R _{6 to} R ₈ are substituted or unsubstituted. It may be bonded to each other via a substituted methylene group, oxygen atom, sulfur atom, or monosubstituted amino group to form a ring. R ₉ and R ₁₀ may be the same or different from each other, and may have a substituent, a linear or branched alkyl group having 1 to 6 carbon atoms, or a substituent. A cycloalkyl group having 5 to 10 carbon atoms, a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, substituted or An unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryloxy group, each group being a single bond, a substituted or unsubstituted methylene group, A ring may be formed by bonding to each other via an oxygen atom, a sulfur atom, or a monosubstituted amino group. ) The electron transport layer contains a compound having a pyrimidine ring structure represented by the following general formula (3) or a compound having a benzotriazole ring structure represented by the following general formula (4): Item 2. The organic electroluminescence device according to Item 1.

(In the formula, Ar ₇ represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group, and Ar ₈ and Ar ₉ may be the same or different, and each represents a hydrogen atom. Represents a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted condensed polycyclic aromatic group, Ar ₁₀ represents a substituted or unsubstituted aromatic heterocyclic group, and R _{11 to} R ₁₄ represent , Which may be the same or different, hydrogen atom, deuterium atom, fluorine atom, chlorine atom, cyano group, trifluoromethyl group, linear or branched alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted An aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, wherein Ar ₈ and Ar ₉ are not hydrogen atoms at the same time Toss )

(4)
(In the formula, Ar ₁₁ represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, Ar ₁₂ represents a hydrogen atom, A deuterium atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and A ₂ represents a substituted or unsubstituted aromatic Represents a divalent group of an aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, a substituted or unsubstituted condensed polycyclic aromatic divalent group, or a single bond, and A ₃ represents a substituted or unsubstituted group Represents a condensed polycyclic aromatic divalent group or a single bond, and B ₁ represents a substituted or unsubstituted aromatic heterocyclic group.) In an organic electroluminescence device having at least an anode, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole transport layer comprises an arylamine compound represented by the general formula (1). 3. The organic electroluminescent device according to claim 1, wherein the organic electroluminescence device comprises an electron-blocking layer containing an arylamine compound represented by the following general formula (5) or (6).

(5)
(In the formula, Ar _{13 to} Ar ₁₆ may be the same as or different from each other, and are substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, or substituted or unsubstituted condensed polycyclic rings. Represents an aromatic group.)

(6)
(Wherein, Ar ₁₇ to Ar ₂₀ may be the same or different, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic, Represents an aromatic group, and n1 represents an integer of 2 to 4.) In an organic electroluminescence device having at least an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode in this order, the hole injection layer contains an arylamine compound and an electron acceptor. And the electron acceptor is trisbromophenylamine hexachloroantimony, tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4TCNQ), and a radialene derivative. The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device is a selected electron acceptor.

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