TWI287408B - Oligoarylene derivatives and organic electroluminescent devices made by using the same - Google Patents

Oligoarylene derivatives and organic electroluminescent devices made by using the same Download PDF

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TWI287408B
TWI287408B TW092122023A TW92122023A TWI287408B TW I287408 B TWI287408 B TW I287408B TW 092122023 A TW092122023 A TW 092122023A TW 92122023 A TW92122023 A TW 92122023A TW I287408 B TWI287408 B TW I287408B
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TW200407047A (en
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Hidetsugu Ikeda
Masahide Matsuura
Hisayuki Kawamura
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Idemitsu Kosan Co
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Description

1287408 (1) 玖、發明說明 【發明所屬之技術領域】 本發明爲關於低聚伸芳基衍生物及利用其之有機電致 發光元件，更詳言之，爲關於發光效率高且可發出藍光的 低聚伸芳基衍生物及利用其之有機電致發光元件。 【先前技術】 有機電致發光元件（以下將有機電致發光元件簡述爲 EL )爲利用經由外加電場，並且藉由陽極所注入之空穴 和陰極所注入之電子的再結合能量令螢光性物質發光原理 的自發光元件。由Eastman Coduct 公司之C.W.Tang等人 之層合型元件的低電壓驅動有機EL元件的報告（C.W. Tang ，S.A.Vanslyke，Applied Physics Letters，51 卷，913 頁 ，1987年等）以來，乃盛行關於有機材料做爲構成材料之 有機EL元件的硏究。Tang等人爲於發光層使用三（8-羥基 喹啉鋁），於空穴輸送層使用三苯基二胺衍生物。層合構 造之優點可列舉提高空穴對於發光層的注入效率，將陰極 所注入之電子予以阻擋並且經由再結合提高所生成之激發 子的生成效率，令發光層內生成的激發子封入等。此例之 有機EL元件的元件構造已熟知有空穴輸送（注入）層，電 子輸送發光層之二層型，或空穴輸送（注入）層’發光層 ，電子輸送（注入）層之三層型等。此類層合型構造元件 爲了提高所注入之空穴與電子的再結合效率’乃對元件構 造和形成方法下功夫。 1287408 (3) 之低聚伸芳基衍生物。
Ar 1 -Ch~Ar2 ( 1) (式中，Ch爲具有至少一個經取代或未取代之核碳數μ〜2〇 個的縮合芳香族環之基。
Ar1及Ar2分別爲經取代或未取代之核原子數5〜30個之 伸芳基，可爲相同或相異。）
Ch1 ~L~Ch2 (2) (式中，L爲連結基。Ch1及Ch2分別爲具有至少一個經取代 或未取代之核原子數14〜20個的縮合芳香族環之基，可爲 相同或相異）
Ar3— (L1)a —Ch3— (L2)b—Ar4 (3) (式中，Ch3爲經取代或未取代之核碳數14〜20個的伸芳基 )° L1及L2分別爲連結基，可爲相同或相異。a及b分別爲 〇〜1之整數。
Ar3及A〆分別爲經取代或未取代之核原子數5〜30個的 芳基，可爲相同或相異。 -7- (4) 1287408 但，Ch3爲經取代或未取代之芘殘基時，Ar3和/或八〆 爲經取代或未取代之Θ -萘基衍生物）
Ar5 —Ch4— (Ar7)n—L3— (Ar8)m —Ch5 —Ar6 (4) (式中，L3爲連結基。Ch4及Ch5分別爲經取代或未取代之 核原子數14〜20個的伸芳基，可爲相同或相異。 聲
Ar5及Ar6分別爲經取代或未取代之核原子數5〜30個的 伸芳基，可爲相同或相異。
Ar 7及Ar 8分別爲經取代或未取代之核原子數5〜30個的 伸芳基，可爲相同或相異。h及m分別爲0〜1之整數）。 又’本發明爲提供於陰極和陽極間將至少一層或多層 含有發光層所構成的有機薄膜層夾住之有機EL元件中， 該有機薄膜層之至少一層爲含有前述一般式（1)〜（4)任 一者所示之低聚伸芳基衍生物做爲單獨或混合物成分的有 ® 機EL元件。 【實施方式】 用以實施發明之最佳形態 本發明之低聚伸芳基衍生物爲下述一般式（1 )或（2 ) 所示者。
Ar1 — Ch- Ar -8- 1287408 (5)
Ch爲具有至少一個經取代或未取代之核碳數14〜20個 的縮合芳香族環之基。
Ch所示之縮合芳香族環可列舉菲，芘，窟，三鄰伸苯 或菲等，且以ΪΕ或窟爲佳。
Ar1及Ar2分別爲經取代或未取代之核原子數5〜30個的 芳基，可爲相同或相異。
Ar1及Ai:2所示之經取代或未取代之核原子數5〜3〇個的 方基例可列舉本基，1 一蔡基，2 -蔡基，1 一葱基，2-蒽 基，9 —蒽基，1一菲基，2 —菲基，3-菲基，4 一菲基，9 非基’ 1 一蔡並蔡基’ 2—蔡並蔡基’ 9 一蔡並蔡基，1 一拓 基，2-芘基，4一班基，2—聯苯基，3 —聯苯基，4一聯 苯基，對一第三苯基—4 一基，對一第三苯基一 3_基，對 —第三苯基一 2—基，間一第三苯基一 4 —基，間一第三苯 基一 3—基，間一第三苯基一 2 —基，鄰一甲苯基，間一甲 苯基，對一甲苯基，對一第三丁基苯基，對一（2 一苯基丙 基）苯基，3 -甲基一 2 —萘基，4一甲基一1一蔡基，4一 甲基一 1—蒽基，4’一甲基聯苯基，4’’一第三丁基一對— 弟二苯基一 4 一基，苟基等。
Ch1 —L — Ch2 (2) 單鍵，亞甲基，伸 內酯環，胜肽基等 L爲連結基。此連結基可列舉例如 乙基，二甲基亞甲基，二苯基亞甲基， -9- (6) 1287408 構造者，特別，以單鍵爲佳。此些基亦可被取代。 ch1及ch2之縮合芳香族環之例可列舉同前述Ch所示之 縮合芳香族環。 前述一般式（1)爲以上述一般式（3)所示者爲丨圭。
Ch3爲經取代或未取代之核碳數14〜20個的伸。止匕 伸芳基之例可列舉菲，芘，窟，三鄰伸苯或驼等之二價殘 基，且以芘或窟之二價殘基爲佳。 L及L·分別爲連結基，可爲相问或相異。此連結基之 例可列舉同前述L所示之連結基。此些基亦可經取代。&及 b分別爲0〜1之整數。
Ar3及Ar4分別爲經取代或未取代之核原子數5〜3〇個的 芳基，可爲相同或相異。此芳基之例可列舉同前述Ar1及 Ar2所示之芳基。 但’ Ch3爲經取代或未取代之芘殘基時，Ar3和/Ar4爲 經取代或未取代之/3 -萘基衍生物。 前述一般式（2)爲以上述一般式（4)所示者爲佳。 L3爲連結基。此連結基之例可列舉同前述L所示之連 結基。此基亦可經取代。
Ch4及Ch5分別爲經取代或未取代之核原子數14〜20個 的伸芳基，可爲相同或相異。此伸芳基之例可列舉伸菲基 ，伸芘基，伸窟基，伸三鄰伸苯基或伸菲基等，且以伸芘 基或伸窟基爲佳。
Ar5及Ar6分別爲經取代或未取代之核原子數5〜30個的 芳基，可爲相同或相異。此芳基之例可列舉同前述Ar1及 -10- (7) 1287408 A r 2所示之芳基。
Ar7及Ar8分別爲經取佧— n 乂未取代之核原子數5〜30個的 伸芳基，可爲相同或相輿。f[f _ -、 此伸方基之例可列舉將前述
Ar1及Ar2所示之芳基作成〜僧其 人〜1貝基者。m分別爲04之整 數。 前述 Ch，Ch1 〜Ch5，Ari Ar86F； —甘山 _
Ar〜Ar所不基中之取代基可列舉 鹵原子，.羥基，硝基，氰基，烷基，芳基，環烷基，烷氧 基，芳香族雜環基，芳烷基，芳氧基，芳硫基，烷氧羰基 ，或羧基等。 又，前述L ’ L 1〜L3所示之取代基亦可列舉此些基。 以下示出本發明一般式（1 )〜（4 )所示之低聚伸芳基 衍生物的具體例，但並非限定於此些例示化合物。 -11 - (8)1287408
-12- 1287408
-13- (10)1287408
-14- (11)1287408
-15- (12)1287408
-16- (13)1287408
17- (14) 1287408 C-H32
本發明之低聚伸芳基衍生物使用做爲有機EL元件用 發光材料及空穴輸送材料爲佳。 本發明之有機EL元件爲於陰極和陽極間將至少含有 一層或多層發光層所構成之有機薄膜層夾住的有機EL元 -18- * 1287408 件中，該有機薄膜層之至少一層爲含有前述一般式（1) 〜（4 )任一者所示之低聚伸芳基衍生物做爲單獨或混合物 的成分。 該發光層爲含有一般式（1 )〜（4 )任一者所示之低聚 伸芳基衍生物爲佳，且特別以發光層爲含有主成分爲佳。 又，本發明之有機EL元件爲以該發光層爲再含有芳 基胺化合物和/或苯乙烯基胺化合物爲佳。 苯乙烯基胺化合物以下述一般式（A )所示者爲佳。
(式中，Ar9爲由苯基，聯苯基，聯三苯基，芪基，二苯乙 烯基芳基中選出之基，Ar10及Αι·11分別爲氫原子或碳數爲 6〜20個的芳香族基，Ar9，Ar1G及Ar11亦可經取代。（：爲1〜4 之整數。更佳爲αΛ或Ar7之至少一者爲經苯乙烯基所取代 ° ) 此處，碳數爲6〜20個的芳香族基可列舉苯基，萘基， 蒽基，菲基，聯三苯基等。 芳基胺化合物以下述一般式（B )所示者爲隹。 -19- 1287408 (16)
(B) (式中，Ar12〜Ar14爲經取代或未取代之核碳數5〜40個的芳 基。d爲1〜4之整數）。 此處，核碳數爲5〜40個之芳基可列舉例如苯基，萘基 ，蒽基，菲基，芘基，暈苯基，聯苯基，聯三苯基，吡咯 基，呋喃基，噻吩基，苯並噻吩基，鸣二唑基，二苯基蒽 ，吲哚基，咔唑基，吡啶基，苯並喹啉基，螢蒽基，苊並 螢蒽基，：g基等。還有，此芳基之較佳的取代基可列舉碳 數1〜6個之烷基（乙基，甲基，異丙基，正丙基，第二丁基 ，第三丁基，戊基，己基，環戊基，環己基等），碳數 1〜6個之烷氧基（乙氧基，甲氧基，異丙氧基，正丙氧基， 第二丁氧基，第三丁氧基，戊氧基，己氧基，環戊氧基， 環己氧基等），核原子數5〜4 0個之芳基，經核原子數5〜40 個之芳基所取代的胺基，具有核原子數5〜40個芳基的酯基 ’具有碳數1〜6個烷基的酯基，氰基，硝基，鹵原子等。 前述有機薄膜層爲具有空穴輸送層，且該空穴輸送層 爲含有一般式（1 )〜（4 )任一者所示之低聚伸烷基衍生物 做爲單獨或混合物成分亦可，且特別含有做爲主成分爲佳 〇 以下，說明本發明之有機EL元件的元件構成。 本發明之有機EL元件之代表性元件構造可列舉 -20- ♦ (17) 1287408 (l )陽極/發光層/陰極 (2) 陽極/空穴注入層/發光層/陰極 (3) 陽極/發光層/電子注入層/陰極 (4) 陽極/空穴注入層/發光層/電子注入層/陰極 (5) 陽極/有機半導體層/發光層/陰極 (6) 陽極/有機半導體層/電子障壁層/發光層/陰極 (7) 陽極/有機半導體層/發光層/改善附著層/陰極 (8) 陽極/空穴注入層/空穴輸送層/發光層/電子注入層/陰 極 (9) 陽極/絕緣層/發光層/絕緣層/陰極 (10) 陽極/無機半導體層/絕緣層/發光層/絕緣層/陰極 (11) 陽極/有機半導體層/絕緣層/發光層/絕緣層/陰極 (12 )陽極/絕緣層/穴穴注入層/空穴輸送層/發光層/絕緣 層/陰極 (13)陽極/絕緣層/空穴注入層/空穴輸送層/發光層/電子 注入層/陰極 等之構造。 其中通常以（8 )之構造爲較佳使用，但當然並非被限 定於此。 此有機EL元件通常爲於透光性之基板上製作。此透 光性基板爲支撐有機EL元件的基板，其透光性期望於 400〜700nm之可見光區域之光穿透率爲50%以上，更且使 用平滑的基板爲佳。 此類透光性基板例如以玻璃板，合成樹脂板爲適於使 -21- (19) 1287408 數百Ω /□以下爲佳，更且，膜厚通常爲l〇nm〜Ιμιη，較佳 爲 50〜200nm。 ' 於本發明之有機EL元件中，於如此處理所製作之一 對電極的至少一個表面，配置硫屬化物層，鹵化金屬層或 金屬氧化物層（以下，將其稱爲表面層）爲佳。具體而言 ，於發光層側之陽極表面配置矽和鋁等金屬之硫屬化物（ 包含氧化物）層，又，於發光層側之陰極表面配置鹵化金 屬層或金屬氧化物層爲佳。藉此，可令驅動安定化。 上述之硫屬化物較佳可列舉例如SiOx(lSXS2 )， Α10χ(ΚΧ51·5) ，SiON，SiAlON等，鹵化金屬較佳可列 舉例如LiF，MgF2，CaF2，氟化稀土金屬等，金屬氧化物 較佳可列舉例如 Cs20，Li20，MgO，SrO，BaO，CaO等。 更且，本發明之有機EL元件爲於如此處理所製作之 一對電.極的至少一者表面，配置電子傳遞化合物和還原性 摻混劑的混合區域或空穴傳遞化合物和氧化性摻混劑的混 合區域亦佳。若如此處理，則電子傳遞化合物爲被還原， 且做爲陰離子之混合區域爲更易將電子注入’傳遞至發光 層。又，空空傳遞化合物爲被氧化，且做爲陽離子之混合 區域爲更易將空穴注入，傳遞至發光層。較佳的氧化性摻 混劑爲各種路易士酸和受體化合物。較佳的還原性摻混劑 爲鹼金屬，鹼金屬化合物，鹼土金屬，稀土金屬及其化合 物。 本發明之有機EL元件中，發光層爲具有 ①注入機能；外加電場時可由陽極或空穴注入層注入 -23- (24) 1287408 實施例1 (2，6 —雙（2-萘基）芘（CHI )的合成）
Ar環境氣體下，將2，6 —二溴基芘3克，2 -萘硼酸 3.6克（東京化成公司製）及四（三苯膦）鈀（〇 ) 〇·3 6克（廣 島和光公司製）溶解於甲苯100毫升中，並於其中加入碳 酸鈉5克於24毫升水中溶解的溶液，且迴流10小時後，放 置一晚。 將反應混合物過濾，並以水，甲醇，丙酮洗淨取得 2.9克的淡黃色固體。 測定此化合物之FD - MS (場解吸質量分析）時，對於 C36H22 = 45 4，取得m/z = 454，故鑑定此化合物爲2，6 —雙 (2—萘基）芘（CH1)(產率77%)。 實施例2 (6，12 —雙（1 -萘基）一甘油（CH2 )之合成）
Ar環境氣體下，將6，12—二溴基甘油3克，1 一萘硼 酸4克（東京化成公司製）及四（三苯膦）鈀（〇 ) 〇·3 6克（廣 島和光公司製）溶解於甲苯1 〇〇毫升中，並於其中加入碳 酸鈉5克於2 4毫升水中溶解的溶液，且迴流1 〇小時後，放 置一晚。 將反應混合物過濾，並以水’甲醇，丙酮洗淨取得 3.2克的淡黃色固體。 測定此化合物之FD - MS時，對於C38H24 = 4 8 0，取得 m/z = 480，故鑑定此化合物爲6，12—雙（1 一萘基）—甘油 (CH2 )(產率 85% )。 (25) 1287408 實施例3 (6，12 —雙（9 一菲基，）—甘油（CH3)之合成）
Ar環境氣體下，將6，12 —二溴基甘油3克，9 一菲硼 酸5克（東京化成公司製）及四（三苯膦）鈀（Ο) 〇·36克（廣 島和光公司製）溶於甲苯1 0 0毫升中，並於其中加入碳酸 鈉5克於2 4毫升水中溶解的溶液，且迴流1 〇小時後，放置 將反應混合物過濾，並以水，甲醇，丙酮洗淨取得 4·2克的淡黃色固體。 測定此化合物之FD — MS時，對於C46H2 8 = 5 8 0，取得 m/z = 5 8 0，故鑑定此化合物爲6，12—雙（9 —菲基）-甘油 (C Η 3 )(產率 9 3 % )。 實施例4 (6，12—雙（2-聯三苯基）一甘油（CH4 )之合成 )
Ar環境氣體下，將6，12—二溴基甘油3克，2-聯三 苯基硼酸5克及四（三苯膦）鈀（Ο) 〇·36克（廣島和光公司 製）溶於甲苯100毫升中，並於其中加入碳酸鈉5克於24毫 升水中溶解的溶液，且迴流1 0小時後，放置一晚。 將反應混合物過濾，並以水，甲醇，丙酮洗淨取得 4.2克的淡黃色固體。 測定此化合物之FD — MS時，對於C54H3 6 = 6 8 4，取得 m/z = 6 84，故鑑定此化合物爲6，12-雙（2-聯三苯基）甘 油（CH4 )(產率 79% )。 (27)1287408 TPD232
實施例6(有機EL元件的製造） 於實施例5中，除了使用下述芳香族胺D2代替具有苯 乙烯基之胺化合物D 1做爲摻混劑以外，同樣處理製造有 機EL元件，且同樣測定發光效率。其結果示於表1。 -31 - 1287408 (28) 表l 、------ 一__---- 發光層 發光效率 發光色 宿主材料 摻混劑 (cd/A ) 實施例5 ---- CH1 ------ D 1 11.1 藍 實施例6 —.— CH1 ---—---—； D2 11.5 藍 實施例7 CH2 D1 10.5 藍 實施例8 ---- CH2 D2 10.7 藍 實施例9 CH3 D1 10.2 藍 實施例1 〇 CH3 D2 10.4 藍 實施例1 1 CH4 D1 10.3 藍 實施例1 2 CH4 D2 10.6 藍 比較例1 anl D1 9.0 藍 比較例2 an 1 D2 9.3 藍 實施例7〜12 (有機EL元件的製造） 於實施例5中，除了使用表1所示者做爲宿主材料及慘 混劑以外’同樣處理’製造有機&元件’且且樣測定發 光效率。其結果不於表1。 比較例1 (有機EL元件的製造） 於實施例5中，除了使用下述化合物anl代替CH1做爲 宿主材料以外，同樣處理，製造有機EL元件，且同樣測 定發光效率。其結果示於表1。 -32- (29) 1287408
D2 • 比較例2(有機EL元件的製造） 於比較例1中，除了使用芳香族胺D2代替具有苯乙烯 基之胺化合物D 1做爲摻混劑以外，同樣處理，製造有機 EL元件，且同樣測定發光效率。其結果示於表1。
anl 如表1所示般，實施例5〜12之有機EL元件爲相對於比 較例1及2，取得發光效率高的藍色發光。 產業上之可利用性 -33- (30) 1287408 以上，如詳細說明般，利用本發明之低聚伸芳基衍生 物的有機SL元件，取得高發光效率的藍色發光。因此可 用於做爲全色彩用之有機EL元件。
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Claims (1)

1287408 96. TO· 月日修(更)正本 拾、申請專利範圍 第92 1 22023號專利申請案 中文申請專利範圍修正本 民國96年4月20日修正 I —種如下述一般式（1)或（2)所示之低聚伸芳基 衍生物， Ar 1 -Ch—Ar2 ( 1 ) (式中，Ch爲具有至少一個經取代或未取代之核碳數〗4〜20 個的縮合芳香族環之基， Ar1及Ar2分別爲經取代或未取代之核原子數5〜3〇個的 芳基，可爲相同或相異） Ch1 -L — Ch2 (2) (式中，L爲連結基，Ch1及Ch2分別具有至少一個經取代或 未取代之核碳數I4〜2〇個的縮合芳香族環之基，可爲相同 或相異）。 2· —種如下述一般式（3 )或（4 )所示之低聚伸芳_ 衍生物， Ar3- (L1)a —Ch3— (L2)b—Ar4 (3) 1287408 (式中，CP爲經取代或未取代之核碳數i4〜20個的伸芳基 L及L分別爲連結基，可爲相同或相異，&及b分別爲 0〜1之整數， Ar及AI*分別爲經取代或未取代之核原子數5〜3〇個的 芳基，可爲相同或相異， 但’ Ch3爲經取代或未取代之芘殘基時，Αγ3或/或八〆 爲經取代或未取代之p 一萘基衍生物） Ar5-Ch4- (Ar7)n-L3一（Ar8)m — Ch5一A「6 (4) (式中’ L3爲連結基。Ch4及Ch5分別爲經取代或未取代之 核原子數14〜20個的伸芳基，可爲相同或相異，
Ar5及Ar6分別爲經取代或未取代之核原子數5〜3〇個的 芳基，可爲相同或相異， Ar7及Ar8分別爲經取代或未取代之核原子數5〜3 〇個的 伸芳基，可爲相同或相異。11及m分別爲〇〜；!之整數）。 3 ·如申請專利範圍第1項之低聚伸芳基衍生物，其中 一般式（1)及（2)中’各個縮合芳香族環爲由菲，芘，窟， 三鄰伸苯，茈中選出。 (如申請專利範圍第2項之低聚伸芳基衍生物，其中一 般式（3 )中之Ch3的伸芳基爲由菲，芘，窟，三鄰伸苯及茈 -2- 1287408 中選出的二價殘基，一般式（4)中之Ch4及Ch5的伸芳基爲分 別由伸菲基，伸芘基，伸窟基，伸三鄰伸苯基及伸茈基中選 出之基。 5 ·如申請專利範圍第1〜4項中任一項之低聚伸芳基衍生 物，其中該低聚伸芳基衍生物爲有機電致發光元件用發光材 6 .如申請專利範圍第1〜4項中任一項之低聚伸芳基衍生 物，其中該低聚伸芳基衍生物爲有機電致發光元件用空穴輸 送材料。 7· —種有機電致發光元件，其特徵爲於陰極與陽極間 將至少含有一層或多層發光層所構成之有機薄膜層夾住的有 機電致發光元件中，該有機薄膜層之至少一層爲含有如申請 專利範圍第1〜4項中任一項之低聚伸芳基衍生物做爲單獨或 混合物的成分。 8·如申請專利範圍第7項之有機電致發光元件，其中該 發光層爲含有如申請專利範圍第1〜4項中任一項之低聚伸芳 基衍生物。 9.如申請專利範圍第7項之有機電致發光元件，其中該 發光層爲含有如申請專利範圍第1〜4項中任一項之低聚伸芳 基衍生物做爲主成分。 10·如申請專利範圍第7項之有機電致發光元件，其中 該發光層爲再含有芳基胺化合物。 1 1 ·如申請專利範圍第7項之有機電致發光元件，其中 該發光層爲再含有苯乙烯基胺化合物。 1287408 12.如申請專利範圍第7項之有機電致發光元件，其中 該有機薄膜層爲具有空穴輸送層，且該空穴輸送層爲含有如 申請專利範圔第1〜4項中任一項之低聚伸芳基衍生物做爲單 獨或混合物的成分。 1 3 ·如申請專利範圍第1 2項之有機電致發光元件，其中 該空穴輸送層爲含有如申請專利範圍第1〜4項中任一項之低 聚伸芳基衍生物做爲主成分。
I4·如申請專利範圍第7項之有機電致發光元件，其中 該發光元件爲發出藍光。
-4 -
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US20090009074A1 (en) 2009-01-08
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US7429425B2 (en) 2008-09-30
CN1675149A (zh) 2005-09-28
US20090009073A1 (en) 2009-01-08
JP2004075567A (ja) 2004-03-11
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EP1533290A1 (en) 2005-05-25
EP1533290A4 (en) 2007-07-04

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