CN107957656B - Negative photosensitive resin composition and use thereof - Google Patents
Negative photosensitive resin composition and use thereof Download PDFInfo
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- CN107957656B CN107957656B CN201610986426.8A CN201610986426A CN107957656B CN 107957656 B CN107957656 B CN 107957656B CN 201610986426 A CN201610986426 A CN 201610986426A CN 107957656 B CN107957656 B CN 107957656B
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- 239000011342 resin composition Substances 0.000 title claims abstract description 49
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- -1 polysiloxane Polymers 0.000 claims abstract description 20
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims abstract description 11
- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 125000000129 anionic group Chemical group 0.000 claims abstract description 3
- 239000000178 monomer Substances 0.000 claims description 32
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 8
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 7
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000005530 etching Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910001868 water Inorganic materials 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 102100027370 Parathymosin Human genes 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QZPSXPBJTPJTSZ-UHFFFAOYSA-N aqua regia Chemical compound Cl.O[N+]([O-])=O QZPSXPBJTPJTSZ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- LFFZNVNUDKIELA-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound C(C(C)C)[Si](OC)(OC)OC.C(C(C)C)[Si](OC)(OC)OC LFFZNVNUDKIELA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0752—Silicon-containing compounds in non photosensitive layers or as additives, e.g. for dry lithography
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Silicon Polymers (AREA)
Abstract
A negative photosensitive resin composition comprising: (A)10 to 50 weight percent of a polysiloxane compound; (B)0.1 to 30 weight percent silicate oligomer; (C)0.1 to 10 weight percent of a photoacid generator, wherein the anionic portion of the photoacid generator is comprised of pentafluorophenyl borate; and (D) the balance solvent. And a use of the negative photosensitive resin composition.
Description
Technical Field
The present invention relates to a negative photosensitive resin composition, and more particularly, to a negative photosensitive resin composition suitable for a low temperature process.
Background
In the manufacturing process of display panels and touch panels, various photosensitive resin compositions, such as positive type or negative type, are conventionally used as materials, and the photosensitive properties of the photosensitive resin compositions are utilized to pattern and cure the photosensitive resin compositions to form members, such as passivation layers, protective layers, or insulating layers.
Transparent conductive layers (such as Indium Tin Oxide (ITO)) used as panel members are required to achieve high transparency and high conductivity; and unlike the On-Cell touch panel, the lighter and thinner in-Cell touch technology (On-Cell) requires operation at lower baking and curing temperatures (e.g., 120 ℃). However, it is known that the hardness of the photosensitive resin composition mainly composed of acrylic resin is less than or equal to 1H and the reliability is remarkably reduced to 0B after baking at 120 ℃; therefore, the conditions of the acrylic resin material such as hardness, etching resistance and the like after low-temperature process do not meet the current requirements.
In view of the above, there is a need for a novel negative photosensitive resin composition that can be fully cured at low temperature and can form a film with excellent properties such as high transparency, high chemical resistance and high hardness, so as to be applied to a semiconductor process with high transparency and high conductivity, such as an in-cell touch panel process.
Disclosure of Invention
The main object of the present invention is to provide a negative photosensitive resin composition which is particularly suitable for low-temperature baking curing and which forms a film having chemical resistance and high hardness.
The negative photosensitive resin composition of the present invention may include: (A)10 to 50 weight percent of a polysiloxane compound polymerized from a plurality of monomers, wherein the monomers comprise siloxane monomers represented by the following formulas (a-1) and (a-2);
wherein R is1Are each independently C1-6An alkyl group; r2 is C6-20Cycloalkyl or C6-20An aryl group; and R3Are each independently selected from the group consisting of C1-6Alkoxy, and aryloxy groups;
(B)0.1 to 30 weight percent silicate oligomer (silicate oligomer);
(C)0.1 to 10 weight percent of a photoacid generator, wherein the anionic portion of the photoacid generator is comprised of pentafluorophenyl borate; and
(D) the balance being solvent.
In the negative photosensitive resin composition provided by the present invention, the polysiloxane compound (a) is used as a main component of the resin composition, and monomers used for polymerizing the polysiloxane compound (a) must include at least monomers represented by the formulae (a-1) and (a-2). In particular, the polysiloxane compound does not include siloxane monomers containing anhydride groups. Wherein, the monomer shown in the formula (a-1) comprises four alkoxy groups connected with silicon atoms, which can provide cross-linking points for condensation polymerization with each other, thereby improving the film-forming hardness and chemical resistance; the monomer shown in the formula (a-2) can be crosslinked with the monomer shown in the formula (a-1), and can further improve the transparency of a formed film. In addition, by exposing (C) the acid generated from the photoacid generator to light, the polysiloxane compound (a) can be further subjected to a condensation reaction to increase the crosslinking density of the resin composition, thereby improving the problem of poor film reliability. Furthermore, in order to increase the resistance of the negative photosensitive resin composition of the present invention (e.g., the resistance to etching by an ITO etchant), the present invention provides (B) the silicate oligomer as a crosslinking agent in the resin composition, and further crosslinks (a) the polysiloxane compound by (C) an acid generated upon exposure to a photoacid generator, to achieve a greater crosslinking density.
In the negative photosensitive resin composition of the present invention, R is R in the siloxane monomer represented by the formula (a-1)1May each independently be C1-6And R is alkyl of1Preferably each independently is C1-3Alkyl group of (1). In one embodiment of the present invention, the siloxane monomer represented by formula (a-1) is tetraethoxysilane.
In the negative photosensitive resin composition of the present invention, in the siloxane monomer represented by the formula (a-2), R2 may be C6-20Cycloalkyl or C6-20Aryl of (2), preferably C6-12Cycloalkyl or C6-12Further preferred is a cyclohexane group or a phenyl group, and most preferred is a phenyl group. Furthermore, R3Can be independently selected from C1-6Alkoxy and C6-20Preferably each independently selected from the group consisting of C1-3Alkoxy and C6-12And more preferably are each independently C1-3Alkoxy group of (2). In one embodiment of the present invention, the siloxane monomer of formula (a-2) is phenyltrimethoxysilane.
In the negative photosensitive resin composition of the present invention, (a) the polysiloxane compound is polymerized from siloxane monomers represented by the formulae (a-1) and (a-2). Wherein the proportion of the siloxane monomer represented by the formulae (a-1) and (a-2) is not particularly limited. For example, the siloxane monomer represented by formula (a-1) may be 30 to 70%, and the siloxane monomer represented by formula (a-2) may be 30 to 70%, based on the total weight ratio of the monomers to the polysiloxane compound (a); preferably, the siloxane monomer represented by the formula (a-1) accounts for 40 to 60%, and the siloxane monomer represented by the formula (a-2) accounts for 40 to 60%.
Further, in the negative photosensitive resin composition of the present invention, the molecular weight of the polysiloxane compound (a) may be 1000 to 8000 g/mol, preferably 1000 to 6000 g/mol, and more preferably 1500 to 4500 g/mol.
In the negative photosensitive resin composition of the present invention, (B) the kind of the silicate oligomer is not particularly limited, and may be represented by the following formula (B-1):
wherein R is4Each independently is C1-6Alkyl groups of (a); and n is an integer of 2 to 10.
In one embodiment of the present invention, the silicate oligomer represented by the formula (b-1) is methyl silicate, which is represented by the following formula:
further, in the negative photosensitive resin composition of the present invention, (C) the kind of the photoacid generator is not particularly limited as long as it is a pentafluorophenyl borate anion moiety containing a strong acid; for example, it may be a pentafluorophenyl borate as shown in any one of formulas (c-1) to (c-2):
in the negative photosensitive resin composition of the present invention, the content of the solvent is the residual amount of other components in the negative photosensitive resin composition, and the residual amount is the residual amount obtained by subtracting the content of other components from the total amount of the negative photosensitive resin composition.
In addition, the invention further provides an application of the negative photosensitive resin composition in a low-temperature baking curing process, wherein the low temperature is below 150 ℃. Preferably, the temperature is 60-150 ℃; more preferably, the temperature is 80-150 ℃.
The known acrylic resin has a problem of poor hardness and reliability due to insufficient reaction after low-temperature baking curing reaction. Therefore, the present invention provides a negative photosensitive resin composition, which can be used as a new generation of insulation layer transparent photoresist, and is particularly suitable for low temperature process; in particular, after the negative photosensitive resin composition of the present invention is cured by baking at a low temperature, the formed film has a high crosslinking density, and the formed film has excellent transparency, good chemical resistance and UV resistance, and high hardness, and can be applied to a semiconductor process having high transparency and high conductivity. For example, when applied to a touch panel, a film formed by the negative photosensitive resin composition of the invention has good chemical resistance and is stable in reliability to chemical agents such as ITO etching solution; and can be used on a transparent insulating layer for a touch panel because the formed film has excellent transparency.
Detailed Description
The following description of the embodiments of the present invention is provided by way of specific examples, and other advantages and effects of the present invention will be readily apparent to those skilled in the art from the disclosure of the present invention. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Synthesis example-polysiloxane Compound
In the present synthesis example, silicone compounds of A-1 to A-5 were prepared in accordance with the composition formulations shown in Table 1 below. The preparation method is roughly described below.
Siloxane monomer and Propylene Glycol Monomethyl Ether Acetate (PGMEA) were stirred at room temperature and 54 g (0.216 g H) of phosphoric acid aqueous solution was slowly added dropwise3PO4Dissolved in 54 g of water), and heated to 110 ℃ to carry out a condensation polymerization reaction for 2 hours. After the reaction is completed, the alcohol and water are removed by distillation. The synthesized weight average Molecular Weight (MW) and polydispersity index (PDI) are shown in table 1.
TABLE 1
TEOS: tetraethoxysilane (tetraethoxysilane), C8H20O4Si, CAS number: 78-10-4
PTMS: phenyltrimethoxysilane (Phenyltrimethoxysilane), C9H14O3Si, CAS number: 2996-92-1
MTMS: methyltrimethoxysilane (Methyltrimethoxysilane), C4H12O3Si, CAS number: 1185-55-3
IBTMS: isobutyltrimethoxysilane (isobutyl (trimethoxy) silane), C7H18O3Si, CAS number: 18395-30-7
STES: dihydro-3- [3- (triethoxysilyl) propyl group]Furan-2, 5-dione ((3-triethoxysilpyl) succinic anhydride), C13H24O6Si, CAS number: 93642-68-3
Examples and comparative examples-negative photosensitive resin composition
In the examples and comparative examples of the present invention, the negative photosensitive resin compositions of examples 1 to 4 and comparative examples 1 to 5 were prepared according to the composition formulas shown in the following table 2. The preparation method is roughly described below.
The photosensitive resin compositions of examples 1 to 4 and comparative examples 1 to 5 were prepared by formulating a polysiloxane compound, a silicate oligomer, a photoacid generator, and a solvent according to the composition formulas shown in table 2, wherein the polysiloxane compound used was the polysiloxane compounds a-1 to a-5 prepared by the above synthesis examples. The silicate oligomer used was methylsilicate 53A (B-1). The photoacid generators used were Irgacure290(C-1), TR-PAG-21608(C-2), Omnicat432(C-3) and Irgacure PAG 121 (C-4). Wherein, the chemical formula of methyl silicate 53A and the used photoacid generator is shown as follows:
methylsilicate 53A (MS-53A): c10H30O13Si4And CAS number: 12002-26-5;
photoacid generator Irgacure 290: CAS number: 1203809-92-0;
a photoacid generator TR-PAG-21608;
photoacid generator Omnicat 432: CAS number: 104558-95-4;
a photoacid generator Irgacure PAG 121;
test example
First, a substrate is prepared, and the surface of the substrate is cleaned by deionized water and acetone. Then, the negative photosensitive resin compositions prepared in examples 1 to 4 and comparative examples 1 to 5 were uniformly coated on the substrate by spin coating, respectively. Next, the negative photosensitive resin composition coated on the surface of the substrate was subjected to soft baking at 90 ℃ for 5 minutes, and directly exposed to light using an ultra-high pressure mercury lamp (exposure energy: 230mJ/cm2) using a mask. Subsequently, development was performed with 2.38% TMAH developer for 60 seconds. Hard baking was carried out at 120 ℃ for 30 minutes. Finally, the substrate and the photoresist layer were washed with secondary water at 25 ℃ to obtain a desired sample with a thickness of 1.5 μm.
< hardness >
The pencil hardness of the sample obtained in the above test example was measured in accordance with 8.4.1 pencil mark hardness test of JIS K-5400-1990. The hardness was measured in pencil hardness, and the results are shown in table 2.
< Corrosion resistance test >
The sample prepared in the above test example was immersed in aqua regia at 40 ℃ for 160 seconds; then, the resultant was immersed in stripping solution N-300 (Ethanolamine 30% + Diethylene glycol monobutylether 70%) at 60 ℃ for 135 seconds. The evaluation results of the etching resistance test are shown in table 2. Wherein the evaluation of the etch resistance test is: excellent X, good o, and poor X.
TABLE 2 (Unit: gram)
As shown in the results of examples 1 to 4 and comparative examples 4 to 5, when the negative photosensitive resin composition (examples 1 to 4) was formulated using the polysiloxane compound containing TEOS and PTMS, the formed film had both better hardness and etching resistance characteristics. In addition, as shown by the results of examples 1 to 4 and comparative examples 1 to 3, when a photoacid generator whose anion portion was composed of pentafluorophenyl borate was used (examples 1 to 4), the formed film simultaneously had better etching resistance characteristics.
From the above test results, it is clearly understood that when the negative photosensitive resin composition of the present invention is prepared using a polysiloxane compound formed from a specific siloxane monomer and a photoacid generator composed of a pentafluorophenyl borate, a film formed not only has transparency but also has high hardness and high chemical resistance when cured by baking at a low temperature (150 ℃ or lower). Therefore, the negative photosensitive resin composition provided by the invention can be used as a new generation of insulation layer transparent photoresist, for example, can be applied to an insulation layer (OC1) and a protective layer (OC2) of a touch panel, and the product has the characteristics of good substrate adhesion, easy development, moisture resistance, etching resistance and the like.
The above-described embodiments are merely exemplary for convenience of description, and the claimed invention should not be limited to the above-described embodiments, but should be limited only by the scope of the appended claims.
Claims (11)
1. A negative photosensitive resin composition comprising:
(A)10 to 50 weight percent of a polysiloxane compound polymerized from siloxane monomers represented by the following formulas (a-1) and (a-2);
wherein R is1Each independently is C1-6Alkyl groups of (a);
R2is C6-20Cycloalkyl or C6-20Aryl of (a); and
R3each independently selected from C1-6Alkoxy and aryloxy groups of (a);
(B)0.1 to 30 weight percent silicate oligomer;
(C)0.1 to 10 weight percent of a photoacid generator, wherein the anionic portion of the photoacid generator is comprised of pentafluorophenyl borate; and
(D) the balance being solvent.
2. The resin composition according to claim 1, wherein (B) the silicate oligomer is represented by the following formula (B-1):
wherein R is4Each independently is C1-6Alkyl groups of (a); and
n is an integer of 2 to 10.
3. The resin composition according to claim 1, wherein (a) the silicone compound is polymerized from silicone monomers represented by formulas (a-1) and (a-2), wherein the silicone monomer represented by formula (a-1) accounts for 30 to 70% and the silicone monomer represented by formula (a-2) accounts for 30 to 70% based on the total weight of the monomers in (a) the silicone compound.
4. The resin composition according to claim 1, wherein the siloxane monomer represented by formula (a-1) is 40 to 60% and the siloxane monomer represented by formula (a-2) is 40 to 60% based on the total weight ratio of the monomers to the polysiloxane compound (a).
5. The resin composition according to claim 1, wherein the siloxane monomer represented by formula (a-1) in the polysiloxane compound (A) is tetraethoxysilane.
6. The resin composition according to claim 1, wherein the siloxane monomer represented by formula (a-2) in the polysiloxane compound (A) is phenyltrimethoxysilane.
7. The resin composition according to claim 2, wherein the silicate oligomer represented by the formula (b-1) is represented by the following formula:
8. the resin composition according to claim 1, wherein (C) the photoacid generator is a pentafluorophenyl borate represented by any one of formulae (C-1) to (C-2):
9. the resin composition according to claim 1, wherein (A) the polysiloxane compound has a molecular weight of 1000 to 8000 g/mol.
10. Use of the negative photosensitive resin composition according to any one of claims 1 to 9 for a low-temperature bake curing process, wherein low temperature means 150 ℃ or less.
11. Use according to claim 10, wherein the temperature is 80-150 ℃.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW105133600A TWI606302B (en) | 2016-10-18 | 2016-10-18 | Negative-type Photosensitive Resin Composition and Use thereof |
| TW105133600 | 2016-10-18 |
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| CN107957656B true CN107957656B (en) | 2020-09-04 |
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| TWI711654B (en) * | 2018-11-12 | 2020-12-01 | 臺灣永光化學工業股份有限公司 | Negative photoresist composition and use thereof |
| CN111443573B (en) * | 2019-01-16 | 2023-06-06 | 台湾永光化学工业股份有限公司 | Negative photosensitive resin composition and use thereof |
| TWI719388B (en) * | 2019-01-16 | 2021-02-21 | 臺灣永光化學工業股份有限公司 | Negative-type photosensitive resin composition and use thereof |
| CN113448164A (en) * | 2020-03-26 | 2021-09-28 | 台湾永光化学工业股份有限公司 | Negative photosensitive resin composition and use thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006018249A (en) * | 2004-06-02 | 2006-01-19 | Toray Ind Inc | Photosensitive resin composition |
| CN102918460A (en) * | 2010-06-09 | 2013-02-06 | 东丽株式会社 | Photosensitive siloxane composition, cured film formed form same, and element having cured film |
| TWI539237B (en) * | 2015-04-17 | 2016-06-21 | 臺灣永光化學工業股份有限公司 | Negative-type Photosensitive Polysiloxane Composition |
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| JP5473239B2 (en) * | 2008-03-25 | 2014-04-16 | 富士フイルム株式会社 | Metal phthalocyanine dye mixture, curable composition, color filter, and method for producing color filter |
| JP5393092B2 (en) * | 2008-09-30 | 2014-01-22 | 富士フイルム株式会社 | Dye-containing negative curable composition, color filter using the same, method for producing the same, and solid-state imaging device |
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- 2016-10-18 TW TW105133600A patent/TWI606302B/en active
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006018249A (en) * | 2004-06-02 | 2006-01-19 | Toray Ind Inc | Photosensitive resin composition |
| CN102918460A (en) * | 2010-06-09 | 2013-02-06 | 东丽株式会社 | Photosensitive siloxane composition, cured film formed form same, and element having cured film |
| TWI539237B (en) * | 2015-04-17 | 2016-06-21 | 臺灣永光化學工業股份有限公司 | Negative-type Photosensitive Polysiloxane Composition |
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| TW201816516A (en) | 2018-05-01 |
| CN107957656A (en) | 2018-04-24 |
| TWI606302B (en) | 2017-11-21 |
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