TW200936567A - Compound having carbazolyl group and use thereof - Google Patents

Compound having carbazolyl group and use thereof Download PDF

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Publication number
TW200936567A
TW200936567A TW098103806A TW98103806A TW200936567A TW 200936567 A TW200936567 A TW 200936567A TW 098103806 A TW098103806 A TW 098103806A TW 98103806 A TW98103806 A TW 98103806A TW 200936567 A TW200936567 A TW 200936567A
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group
substituted
compound
unsubstituted
organic
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TW098103806A
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Chinese (zh)
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Michiko Tamano
Yasumasa Toba
Yoshitake Oryu
Junpei Hayakawa
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Toyo Ink Mfg Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Indole Compounds (AREA)

Abstract

The present invention provides a compound, which is useful in a material for organic EL elements, can be used to manufacture films by evaporation and coating and exhibits high Tg, and provides a compound, which is suitable for use in the organic EL elements emitting blue light. Furthermore, the present invention can provide an organic EL element, which exhibits excellent properties of low-voltage driving, long lifetime, thermal resistance and the like, by using the compound. The present invention provides a compound having carbazolyl that is shown in the following formula [1]: (wherein A represents carbazolyl shown in the following formula [2]; and R1 to R9 each represents a hydrogen atom or a substituent) (wherein Ar1 represents a substituted or unsubstituted monovalent aromatic hydrocarbon group with or a substituted or unsubstitued monovalent aromatic heterocyclic group; and R10 to R16 each independently represents a hydrogen or a substituent).

Description

200936567 • * - ·· ： •六、發明說明： .. ' . ...... ... ..... : ::[祖關申請案::广：」 :乂。本徒 本發明之内容旅關於2008年2月8日所申請；日麟 願.2008-028251及2008年9月:26日所申請之曰奈特系 2〇〇8-247〇2〇 >所包含之主題，並將:此等說明書f ,揭《: '七貧目明確具完整地援用於丰說明書肀乂:: .【發明所雇之技術領域.】 ‘-… _ ·；'· . ..... 本發明係有關二该具有咔唑棊（carbazolyl)之你 .·· ... ....... ... 交‘及使用讀作合物之有機電激，發光元件 久:【先前技術1 . 近年來’在有機:EL元件方面’正尋求延長私 • * . .- . . . . - - :命。對元件之壽命造成影響之厚爾可能有各輕因素ί參 - . .... —.. . ...... ： ' · ：· 專利:文獻:1)。.廣劈之一 ’可能是構成，元衅$材料么 爲: fg 4對it件，壽命造成大幅影拿者。換；¥之v已指:出有声:1?， 件乏使眉環境:滅觸動诗之發熱，使元并之蕰i超遍辧乘威 . . · · ;· ·. · . .... · .· . . . · · ·. . .. . ·, 之#.料之Tg則•造成材料趣畢化而裏生稱為蜻無(darlc 绅〇t) g蜉之現象:此，:K寒赳‘，堯侖發顯呆 .較高:的Tg乏材料。：0 ., ..... ·. . · · · · · ·· · · . - · · · .· · . *· · ··.. . '·：-.·· ·. ；; . . ...... /. V. _ ,然::而.’至今己有將味季衍生豕應用莖各種機能材料、 :電子#料之砵究。咔也骨秦桃‘有電洞輸适性，,具:真看命 熱悻高的構造利用此釋性，已.有例知應標至電子照相咸 光:¾乏電荷輸籩材料或有機EL元件甩¥科等之;^尧。具代’ 表性者可;舉例如：·聚乙烯基咔唑（PVK)和:n,F-二卞$ -4, 4’:-聯笨（CBP)、正廣泛研究释此等做為有機EL元件.用、 321016 200936567 • · . · .. . ·' . · . . · —200936567 • * - ·· : • Six, invention description: .. ' . . . . . . . : :: [Zu Guan application:: Guang:": 乂. The contents of the present invention are related to the application of February 8, 2008; Japanese Lin Yuan. 2008-028251 and September 2008: 26th application of the Naite Department 2〇〇8-247〇2〇> The subject matter included, and: These instructions f, reveals: "The seven slums are clearly and fully applied to the Feng 肀乂 manual:: . [Technical field employed by the invention.] '-... _ ·;'· . . . The present invention relates to the organic galvanism of the carbazolyl, which is used by the carbazolyl, and the use of the reading composition. Light-emitting elements for a long time: [Prior Art 1. In recent years, 'in the organic: EL components' is seeking to extend the private * * . . . . . . - - : life. There may be some light factors affecting the life of the component. -....... . . . : : · ·· Patent: Literature: 1). One of the vast ’ may be the composition, the Yuan 衅 $ material is: fg 4 on the it piece, the life expectancy is a large shadow. Change; ¥ v has been said: out of the sound: 1?, the lack of the eyebrows environment: the touch of the poetry of the fever, so that the yuan and the 蕰i super 辧 辧 辧 . . . . . . . . . . . 超 超 超 超 超 超 超 超 超 超 超 超 超. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . : K 赳 赳 ', 尧 发 显 显 显. Higher: Tg lack of materials. :0 ., ..... ·················································. ...... /. V. _, then:: and. 'To date, there have been a variety of functional materials derived from the season, and the use of electronic materials.咔也骨秦桃' has a hole-transfer adaptability, and it has a structure that uses high heat and high enthusiasm to utilize this release. It has been known to be labeled to electrophotographic salt light: 3⁄4 lack of charge transport material or organic EL component 甩¥科等; ^尧. For example,: polyvinyl carbazole (PVK) and: n, F-dioxin $ -4, 4': - LBP (CBP), is widely studied to interpret this as Organic EL components. Used, 321016 200936567 • · · · .. . · ' . · . . · —

材料(參照非專利文獻:2、.3)。知pVK和咖 .Tg ^ r% V 膜之安定性低.、和元件之壽命極短之問題點。 牝外’低分子之具有味啥棊之辨生物，已有經2價連 結基連辞爾成之噻吩(谢如h咖)衍生物轉 :孕物之報告(參戚專利文獻:】)。然而，使用此等衍^ 點 成冬有機EL元件係具有養光壽命短且色純產不良之問題 Π»» ... ❹ 十外，已有包舍具有峥唾基之化舍物與兰重態發.光化Materials (refer to non-patent literature: 2., 3). Know the pVK and coffee .Tg ^ r% V film stability is low, and the life of the component is extremely short.牝外' low-molecules have the characteristics of miso, and there has been a derivative of the thiophene (Xie Ruh) converted by the two-valent link: the report of the pregnancy (see Patent Document:). However, the use of such a derivative point into a winter organic EL component has a problem of short matte life and poor color purity. »»» ❹ 外 , , , 已有 已有 已有 已有 已有 已有 已有 已有 已有 已有 已有Heavy state

: _ . · * ' , " ... 坐骨架之化合物、矣東G 稀棊衍生物、花_ry_e)街生物、♦豆素把生 :j料$發赛特料的聲光元件$報告(參瑪專利文獻2至3 > 声一方$，低分丰冬具之衍生物，已有經V ?價绛錶备^绛而成今黃衍:篆物冬報告_ 0 ,之參告(_專，文獻:5:5 7〕。:此等化合物虫於皆在與 蒽，之間真亨.4結棊，故相較於袁接:鍵結，可觀察到^g年: ..隹$姨$ p結果丨在高溫下之環境測第中，真有發先壽命 ..P ：/ _ ,;； ..... .. - -.. . .. -> . ' . . .; :#4利文聲l·::畴任靜士^安達千波矢^村田:英幸共 w編者;有機EL處$ $ ; Ohm舍司，.2004年發行,139 ；!: 非專利.文獻 2 : Applied Pl^sics Letters, .2001 年發 行:，78 ^ .279-281 I · .非專利文獻.3' Journal of the American Chemical 321016 200936567: _ . · * ' , " ... The compound of the skeleton, the G G G 棊 、 、 、 、 、 街 街 街 街 街 街 街 街 街 : : : : : : : : : : : : : : : : : : : 声 声Report (Shenma Patent Literature 2 to 3 > Sound One Party, a derivative of low-grade winter ware, has been prepared by V-price 绛 绛 绛 今 今 今 衍 衍 衍 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆 篆(_Special, essay: 5:5 7).: These compounds are all in between and 蒽, between Zhenheng. 4 knots, so compared with Yuan: bond, can observe ^g years: ..隹$姨$ p The result is in the environmental test at high temperature, there is a real life..P :/ _ ,;; ..... .. - -.. . .. -> . ' . . . ; : #4利文声 l·:: domain Ren Jingshi ^ Anda thousand wave vector ^ Murata: Ying Xing a total of w editor; organic EL at $; Ohm She, 2004 issued, 139;!: Non-patent Document 2: Applied Pl^sics Letters, . 2001 Issued: 78 ^ .279-281 I · Non-Patent Literature. 3' Journal of the American Chemical 321016 200936567

Society, 2001 年，123 卷，4304 頁 1利爻獻.1 :日本#開2004-217557被公報 專利文獻2 :日本特開2加3-133075 .號公報 • - - · · ..... .... ...... · . 專，利文獻.3 :日本特開20(17-194241 ¾公報 ... . · _ -.； 專利文獻4 : 1132003-0215667號説明書. ...... " • . · ... .... ..... 專利:文獻5 : ¥02005/113531號小冊 ... ''' . ❹ 專利文獻6 :日本特開2007-63501號公報 專利文獻7 :日本#開2007-1317:22號公報 :【發明:何容】 - .'V ' . .. ： ； ' . ' ·· '. ·；. ' (鼙明欲解決的錁題):::r _ ::. : \本發明之—實施態樣之課題在於提供對有機’虹 :用材料為有用可進抒蒸鍍及塗佈，且顯示高的Tg;之具 · ； -：：' ： ' - ：·· - - ； ^ 有咔唑基之化合物。此外，提供特別適合做為發出藍光之 ::有機H:件使用::之具有基之化善物。:並且，:可提供因:: . . .使用此化合物而顯示低電壓驅動、長壽I、对熱性等優良 ❾.之.無性C有:機.3EL·元:件.： ' :(解決課題:的.手段):: .· *' .; - ' *· .· · . - · :本發明人等為了解決愈述各間題雨致力研究後之結 I..V ' ；：· . ' ' '果’遂完成本發明。. 換言i，本發明之一者i態樣係關於一種姜 .之化合物’:係如下述通式[T]所示:： 通式 321016 200936567Society, 2001, Vol. 123, 4304, 1 爻 爻.1: Japan #开2004-217557 is published in the Gazette Patent Document 2: Japanese Special Open 2 Plus 3-133075. Bulletin • - - · · ..... .... ...... · . Specialized, Lee Literature. 3: Japanese Special Open 20 (17-194241 3⁄4 Gazette... . _ -.; Patent Document 4: 1132003-0215667. ..... " • . . . . . . . . Patent: Document 5: ¥02005/113531 Booklet... ''' . 专利 Patent Document 6: Japan Special Open 2007 -63501 Patent Document 7: Japan #开2007-1317:22 Bulletin: [Invention: He Rong] - .'V ' . . : ; ' . ' ·· '. ·;. ' (鼙明Solved problem):::r _::: : The present invention - the object of the implementation is to provide organic Thong: the material is useful for vapor deposition and coating, and shows a high Tg; ;:::' : ' - :·· - - ; ^ Compounds with carbazolyl. In addition, they are especially suitable for emitting blue light:: Organic H: Parts use:: Object: and,: can provide the cause:: . . . using this compound to show low voltage drive, longevity I, heat and so on. Sex C: machine. 3EL·yuan: piece.: ' : (solving the problem: means.):: .· *' . . - ' *· .. · - - : The inventor of the present invention I..V ' ;:· ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' As shown in the following general formula [T]:: General Formula 3216 200936567

....- ..... * · . . (式中，Α表示下述埠式:[2 ]所示之咔唑基R1:至f分別獨 Ο 立地表未氫原子、鹵素肩子、取代或来取代乏1價脂肪. 匕脂肪族雜環基、取鱗未取贼!償芳香族雜環基、 IΛ > ^ ^ ^ .V ^ 通式 K] : ::. Λ....- ..... * · . . (wherein Α represents the following formula: [2] carbazole group R1: to f, respectively, the surface of the surface is not hydrogen atom, halogen shoulder , substituting or replacing the lack of monovalent fat. 匕 aliphatic heterocyclic group, scaly not taken thief! compensation aromatic heterocyclic group, I Λ > ^ ^ ^ .V ^ general K]: ::. Λ

货’Ar麵_或未取代之1償芳香纏基:'、或是 .:':或冬取:代之1價芳章族减環基沈。至别 卜你子、虑素原卞、取代或紗代之1:價^ :S未取代之」價:_ 讀％基、取代麻取_ 1價芳香族祕i、氰基、烧 .’ t 方:^本、烷硫棊、芳硫基、取代胺基、醯棊、烧氧 ...基.'芳氧n基、裨磺酿基、.或芳磺醯基）。.广 .:此外’本發明之一實施態樣係關於如上述之具有咔唑 土之化合物’其中:? R5係下述通式[3]所示之取代或未取代 ·. - ' · ' 321016 200936567 \ 之苯基者The goods 'Ar face _ or unsubstituted 1 compensation aromatic entanglement: ', or .: ': or winter take: instead of the 1 price of the Fang Zhang family reduce the base sink. To the other, your child, the original element, the substitution, or the yarn of the 1: price ^ : S is not replaced by the price: _ read the % base, replace the hemp _ 1 price aromatic secret i, cyano, burning. Formula: ^, alkylthiophene, arylthio, substituted amine, hydrazine, oxygenated .... 'aryloxynyl, sulfonyl aryl, or arylsulfonyl).广广: In addition, an embodiment of the present invention relates to a compound having oxazoline as described above, wherein: R5 is a substituted or unsubstituted type represented by the following formula [3]. 321016 200936567 \Phenyl

.或未取代之:1價脂肪族炉某“氨原子、齒素原子、取 。絲、取代絲取叙=脂3:未取狀讀:芳4 之I鮮香族轉基、Λ基、貌魏代矣未取代 •基、取代胺基 基、或芳磺醯基，R17至俨可於夂他芳氧_基、烷續醯 ::其.此外，本發明之-實_祿_ 之化S物’其中:，:紅係取代或未取代之蜂歡6至18之1 :價芳香赛烴棊、或是取代或表取代之碳數2至is之1價芳 •香族雜環基者':· .. , ；. . . 此外’本發明之一實施態樣係關於如上述之弄有味峻. • |>- ' · . *' ，之化合物，其中，Ar:1係下述通式[4]所示之取代.或未乘 代之笨基者 . . . -.·. . .通式[4]Or unsubstituted: a monovalent aliphatic furnace "ammonia atom, dentate atom, take. silk, substituted silk extract = fat 3: not taken reading: fang 4 I fresh fragrant base, sulfhydryl,魏 魏 魏 矣 矣 矣 、 、 、 、 、 、 、 、 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 魏 , , , , , , , , s S of which::: red substituted or unsubstituted bee venom 6 to 18 of 1: valence aromatic hydrocarbon oxime, or substituted or substituted carbon number 2 to is 1 valent aromatic fragrant heterocyclic Basics ':·.., ;. . . In addition, one embodiment of the present invention relates to a compound as described above. • |>- '. . . . , a compound, wherein, Ar:1 It is a substitution shown in the following general formula [4] or a non-substituted stupid base. . . -.·. . . .

321016 200936567 - *·(式中，R22至R26分別獨立地表示氫原子、鹵素原子、取代 '或朱取代之1價脂肪族烴基、取代或未取代之1價芳香族 -· -· ,. '. 烴基、取代或未取代之l·價脂肪族雜環基、取代或未取代 之1價芳香族雜環基、氰盖、燒氧基、芳氧基、烷硫基、. ... · .. ... ... ' · - . - ' 芳硫基、取代胺基·、.醯基、烧氧幾基、芳氧裁基、燒續酉藍 ..... ... :· . ·. 八基、或芳磺醯基Ϊ :: * t ....· : .. - . : · * 此外，未發明之一實施態瑗係關於如上遂之真有咔唑 基之化合物，其中，至E16係氳原子者。5 ® 此外，本發明之一貪施態樣係關於一種有機電激發光: . · . · . . · . ·. ' . . 元件S材料，.係含有上述之任一種真有Κ基之化合物而 ::此外，本發明之一實施態樣係關於一種有機;電激發光 元件，係梦一對電叙間形成複教層有機膚而戒有無電激 . -. ... .. . · . - . .發光元#，:其中‘，:前述有滅層乏，至少一層係含:有.土述之有 ::機:電激發光元_件用蜂料雨成。 β 此外..，本發朋之一實施態樣係關於一_輕宥ά電檄發光' 元件，係於一對電間形成:發:先層或包含發先養之複叙層 ... · ... .. ...... - :有機層而成之有機電.激發光元件，其中' :前述發光層係含 . .- · ...... 有i述之肴機電激發光元件用材料而:成。. ； ..... ：；-_.·. . -· ；· ' .::v此外>.本發明之一實施態樣係:關於如上述:之有機電激: . · - · : * ' —發光元件，其中:，I光層係復含有硪先發光材料雨义者。 ..... · - · . .' . *- · . · ; - 此外:，本發明之一實施態樣係關於如上述之有機電激： … ... ... ·; . . . · 發光元件，其中，發光層係藉由塗佈而成膜所成者。 ; .-. - ; ' .、 ... · 广 (發明的敢果： 321016 200936567 v .根據本發明乏一實施態樣，將具有咔唑基之化合物做 -... · - ·.· .... ..... 為有機EL元件.甩#料使用之有機EL元件V儀以低電壓驅 • · · · '· . . ...... . · . .. · ·' 動，且壽命長。因此，適合做為壁掛式電視等平面顯示:器 ；： ..... 或平面發光體使用。此外，:可應用至影印拽或印表機等之 .· ·· ： · · . - · - .... 光源、液晶顯示器或計量儀器類等之光源、顯示板、標示 ……燈等 / :【實施方式.】乂 V:::: Ϊ》 . . - . · ... - · . · ... :: 以下，詳細說明未發明。'.: 本發明之一實:施態樣係關:於—種具有咔唑基之;化合 • · ’ - · . .物，係如卞述通式[1]所示。：.，321016 200936567 - *· (wherein R22 to R26 each independently represent a hydrogen atom, a halogen atom, a substituted 'or a substituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic---., '. a hydrocarbyl group, a substituted or unsubstituted l. valent aliphatic heterocyclic group, a substituted or unsubstituted monovalent aromatic heterocyclic group, a cyanide cap, an alkoxy group, an aryloxy group, an alkylthio group, ... .. ... ' ' - - - - 'Arylthio group, substituted amine group, fluorenyl group, alkoxy group, aryl oxygen group, burning indigo..... ······························································· Among them, to the E16 system atom. 5 ® In addition, one of the inventions is related to an organic electroluminescence: . . . . . . . . . . . . . . . . Any of the above-mentioned compounds having a sulfhydryl group: In addition, one embodiment of the present invention relates to an organic electro-optic element, which is a pair of electricians that form a resurrection layer of organic skin with or without electrical stimulation. -. ... .. . . . - . . . #,:中的,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, The pattern is about a _ 宥ά 宥ά 宥ά ' ' ' element, is formed in a pair of electricity: hair: the first layer or contains the first resurrection layer ... ... ..... ..... - : Organic light made of organic layer. Excitation light element, where ': The above-mentioned light-emitting layer contains . . . . --...... The material used for electromechanical excitation of optical elements is: ..... :; -_.·. . -· ;· ' .::v Further >. An embodiment of the present invention: regarding the organic electromagnet as described above: . · - · : * '-Light-emitting element, wherein: I-light layer contains a luminescent material of the first luminescent material. ..... · - · . . . . . - - - - - - In addition: one embodiment of the present invention The invention relates to an organic electro-excitation as described above: a light-emitting element in which a light-emitting layer is formed by coating a film. . . . , ... · Guang (Invented Dare: 321016 200936567 v. According to the invention, there is a combination of carbazole groups Do-... · - ··· .... ..... for the organic EL device. 甩# material used in the organic EL device V instrument with low voltage drive · · · · '· . . . .. . . . . . · · ' Moving, and long life. Therefore, it is suitable for use as a flat display such as a wall-mounted television: ..... or a flat illuminator. In addition, it can be applied to photocopies or printers, etc. · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · : [Embodiment.] 乂V:::: Ϊ》 . . . . . . . . . . . . '.: One of the inventions is as follows: the traits of the genus: the oxazolyl group; the compounding · · ‘ - · . . . , as shown in the general formula [1]. :.,

入通式[1] 通式f 1 ]中乏Έ1.至於分別獨立地表示氫原子、鹵:素原. 子、取代或未取代之1:價脂肪族烴基、取代或米取代之1 • · . ·· - · . ........ 價芳香族烴基、取代或未琅代之1:價脂.妨族擁環基、取代. 或未取代之ί .價芳香族雜環基、氰基、:烷氧墓:、关氧基' - ' ' · ·. · . ' · · 烧硫基、芳硫基、取代胺基、醯基、烷氧羰基、芳氡幾基、 • ... ' ； , ·· , .... · . 烷磺龜基、:或芳磺酶基。: ' ' * - ·. · · ' . ' · : . · ..... 在此，鹵素原手可舉例如:氟原手、氯原!子.、.漠原子、 .... . · 碘原子。 在此，1儂脂肪族烴基以碳數；I至18之1價脂肪族.烴 10 321016 200936567 • ： . · · , • . . . . . . . · . . · · . +·-.. - \ · . ' · ' 基為佳。如此之1價腊肪族烴基不限定於以下之例子，可 . . . . - · -. - ' . ' . . . 舉例如:烷塞、烯基（炔基:環烷基。:： , ,- - ·'.·..·· ·-···..· 此外，烷基可舉例如::甲基、乙基、丙基、異丙基、 - ·. .. -. 丁基、異丁基、二級丁基、三級丁基 '戊基、異戊基.、己) 基、庚基、辛基、癸基、十土燒基、十五娱•基、+八燒基. 之襖數1至18之烷基。：’ ，此外，烯墓可舉例如：乙烯基、1-丙烯塞、2-丙烯基、 異丙稀基丁稀基、+:.2-丁_婦基-.V.3.-丁.稀基、.1-辛.稀基 • · · · 微：1-癸烯盖、F十入烯基碳數2至18之烯蠢。 .... ..... . ' .… …：\ .. ：·'.. 此外，炔基可奉例如:乙块基、1-丙炔基、2-两炔基、Γ .. ............ .·>.·· . ： . ·. · · 1-丁炔盖r 2-丁块基、3,丁炔基、1-辛块基、1-癸炔基、 ： · - · :1-十八炔基之礙數2至18之炔基。 ·.· .·. . . · . ·.···. . . · . · ·........ 此外，環燒基以破數3至18之環烷基為崔。如此:之環 . · . · ... . 蜣基不限定於以下之例子:，可舉例如環芮墓、壤丁基:、二: .赛戊基、環己基、:瓖庚基:、環辛基:、瓖十八基。::::::..，丨^ .；'· ； - v , . ； ' ；·：.. - : -.."；： ' - . ... . ；;： :::❹::：::產％ U:.價芳.香綠烴基寸奉树如::1:價單參、稠環^ :集合烴基：..二、 6：^. 18^1¾^¾ ： '..··· ...... . : ... .·. ........... ... : ..... ···.'..· ... .·. ... - - 芳香族烴基為佳。如此之1:價單環芳香族煙基不限定於以v : .:下4游子，:可舉例如::苯基、鄭甲苯基、.間甲苯.基、對甲: ' . ' - · · ； . · ... : / 苯基、2, 4-二::曱笨基·、對異丙苯基、三甲苯基·。/丨:: '-· .···+. ' . .····._. . 此外，、1價稠環烴基以破數ία至18之1價稠環烴基 .為隹ώ如此之Γ價稠環烴基不限定於.以下之例子，可舉购 如：1-萘基、.2-萘基、卜蒽基、2-蒽基、5-蒽基、:1-菲基、 ... - · ·- 11 321016 200936567 9-菲基、1-苊基（acenaphthyl)、2_奠基（azulenyl)、卜 絲（pyrenyl)、2-聯伸三苯基（2〜triphenylenyl)。 此外，1價環集合烴基以碳數12至18之丨價環集合 烴基為佳。如此之1價環集合烴基不限定於以下之例子， 可舉例如：鄰聯苯基、間聯苯基、對聯苯基^ 此外，1價脂肪族雜環基以噥數3至18之i價脂肪族 雜環基為佳。如此之1價脂肪族雜環基不限定於以下之例 ❾子，可舉例如：2-吡唑基、1-哌啶基、N_嗎啉基、2_嗎啉 基。 此外，1價芳香族雜環基以碳數2至18之丨價芳香族 雜環基為佳。如此之1價芳香族雜環基不限定於以下之例 子，可舉例如·二α坐基、3-曙二哇基（〇xadiaZ〇lyl)、2-°夫喃基、3-σ夫喃基、2-嗔吩基、3-嘆吩基、1-°比洛基、2- r 吡咯基、3-吡咯基、2-吡啶基、3-吡啶基、4-吡啶基、2-井基、2-嗜唑基（oxazolyl)、3-異鳄唑基、2-噻唾基 ❿ （thiazolyl)、3-異噻唑基、2-咪唑基、3-吡唑基、2-喹琳 基、3-啥琳基、4-啥淋基、5-哇琳基、6-啥琳基、7-喧琳 基、8-喧淋基、1-異啥琳基、2-喧曙嘴基（quinoxalinyl)、 2-苯并吱喃基、2-苯并嗟吩基、N-吲11 朵基（indolyl)、N-°卡咬基、N-W咬基（acridinyl)、2-M苯基、3-疏苯基、聯 咕1*定基、哪琳基（phenanthrolyl)。 此外，烷氧基以碳數1至8之烷氧基為佳。如此之烷 氧基不限定於以下之例子，可舉例如：曱氧基、乙氧基、 丙氧基、丁氧基、三級丁氧基、辛氧基、三級辛氧基。 12 321016 200936567 ., ... - 此外，芳氧基以碳數6至14之芳氧基為佳。如此之芳 ·' . ...... r .氧基不限.定於以下之例子，可舉例如：:苯氧基、4-三銀丁 墓苯氧基、1-萘氧基、.2-萘氧基、9-蒽氧基。 . -· · • · .... · - · . 此外，烷硫基以碳數1至8之烷硫基為佳。如此之烷 ；' . . . .硫基不限定於以下之例年，可舉例如::甲硫基、乙硫基:、 ... · ' 三級丁硫基·'己:硫基、辛硫基。广: ...... .,. - 此外，芳丨硫基以碳數6至14之芳硫基為^：。如此之芳 ... ...... ...... .... . 硫基不限定於以下之例手:，％舉例如::苯硫基、2-甲墓苯 分硫基、4-三級丁塞苯硫基。:: 此外，取代胺基以碳數2至26之取代胺基為佳。如此 之取代胺基不限定於以卞之例子，可舉例茹:甲基胺基/、 ..... .. .. . ' -； . J-乙基胺基、Ν，Ν-二乙基胺基、Ν，Ν-二異丙基胺基、:N:，- · :胺基、N-寒甲基胺基、Ί^Ν-丄(:苯甲基）按基:、沿装:乂 (基胺基、Ν-苯基甲基涵墓vN，:N-二:苯基胺:基、Ν，:Ν-雙 - * ^ ^ . ;八甲苯基）胺基:、:N.，.N“雙(對:曱苯基）胺基:、N，:N-趣(條装基 .(0胺基 '雙(4-甲.基）聯苯基」胺塞:、1-«-萘基-]^苯基胺::: . .... ..... ·.·；. . . ： .r : . · /'； :基、Ν-:汊-萘基-Ν-苯基胺基。：:·' 此外，醯基以碳數.2至14之醯基為佳。如此之醯基不 • · · . ....... ... , .. · . · 限定於:以下之例子，可舉例如：:乙醯基、丙「醯基、新戊醯.: , ' .. ::基、環己墓羰基、苯甲醯墓、甲苯曱醯基、曱氧苯甲醢基、:: .'.·, ; 丨.. . . 苯丙烯醯基。：…： 此外，烷氧羰基以碳數2至14之燒氧羰基為佳。如此 之烷氧羰基不限定於以下之例子，可舉例如：甲氧獄基、 • . ..... ; 乙氧羰.基、苯曱氧羰基。 * . - · · 13 321016. 200936567 此外，芳氧羰姜以碳數,2至14之芳氧幾基為佳。如此 之芳氧羰基木:限定於以下之例子、，:可舉例如:：苯氧無基、 .萘氧羰基。：，:v; 此外，烷磺醯墓以碳數.2至14之烷確醯基為佳。如此 - · · 之烷續醯基不限定於以下之例子，可舉例如：f磺醯基、 ' .’. .... .. 乙磺醯基、丙磺醯基ό 二此外，芳磺醯基以破數2至14之芳磺|1基為佳。如此: . ·· Ο 之芳磺醯基不限定於以下之例子，可舉例如：苯磺醯基、 .... . . .： . 對甲苯磺醯基。 · ...... ' · · ' · ''.*· * - · * . * - . , . * . * . * *. * 1等R1至R9中之1價腊肪族烴基、芳香族烴基、脂肪 . ;- · .· .· , .... … ·. ...' ... ,· .族雜環基、芳香族雜環基也可再經其他取代基氧代:。如此 之取代基可舉例如：鹵幸原子:、:氰基::、嬈氧基…芳氧基、: 烷硫;&、芳硫基、束代胺基、醯塞、.烷氧羰基芳氧無基、: '烷磺政基、:或芳磺:醯基#。此等取戎基之例子::可 ^ ： . ' V ：· .述者： ❹:厂迷式:t 11 中:之上In the general formula [1], the general formula f 1 ] is deficient in 1. As for the hydrogen atom, halogen: protope, substituent, substituted or unsubstituted 1: valency aliphatic hydrocarbon group, substitution or m substitution 1 • . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . , cyano group, alkoxy tomb:, oxy group '-' ' · · · · · · · · Sulfur-based, arylthio, substituted amine, fluorenyl, alkoxycarbonyl, aryl fluorenyl, ... ' ; , ·· , .... · . Alkanesulfonate, or arylsulfonyl. : ' ' * - ·· · · ' . ' . . . . . . . Here, the original halogen can be, for example, a fluorine precursor, a chlorine source, a child, a desert atom, .... · Iodine atom. Here, 1 侬 aliphatic hydrocarbon group is in carbon number; 1 to 18 valence aliphatic. Hydrocarbon 10 321016 200936567 • : . . . , . . . . . . . . . . . . . . . . . . . . . . - \ · . ' · ' The base is good. Such a monovalent waxy aliphatic hydrocarbon group is not limited to the following examples, and may be, for example, an alkyl stopper or an alkenyl group (alkynyl group: cycloalkyl group::: , Further, the alkyl group may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, or a butyl group. , isobutyl, secondary butyl, tert-butyl 'pentyl, isopentyl., hexyl), heptyl, octyl, decyl, decyl, ketone, kiln An alkyl group having a number of from 1 to 18. : ' In addition, the olefin tomb can be, for example, vinyl, 1-propene plug, 2-propenyl, isopropyl butyl, +: 2-butyl-.V.3.-butyl. Dilute base, .1-octyl. dilute base · · · · Micro: 1-decene cap, F-decene alkenyl carbon number 2 to 18 olefin stupid. .... ..... . ' .... ...:\ .. :·'.. In addition, the alkynyl group can be, for example, an ethyl group, a 1-propynyl group, a 2-alkynyl group, a fluorene group. .............·>.·· . . . . . . . . 1-butyne cover r 2-butyl, 3, butynyl, 1-octyl, 1-decynyl, : - - : 1-octynyl group is an alkynyl group having 2 to 18 hindrance. ··· .·················································· Such a ring: · · · · · 蜣 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 不 芮 芮 芮 芮 芮 芮 芮 芮Cyclooctyl: 瓖 18 base. ::::::..,丨^ .;'· ; - v , . ; ' ;·:.. - : -..";: ' - . . . ;;: :::❹ :::::Production % U:. Price fragrant. Fragrant green hydrocarbon base 奉 树 如 :: 1: price singly, fused ring ^: collection of hydrocarbon groups: .. 2, 6: ^. 18^13⁄4^3⁄4 : ' ..··· ...... . : . . . . . . . . . . : ..... ···.'..· ... ..... - - Aromatic hydrocarbon group is preferred. Such a 1: valence ring aromatic cigarette group is not limited to v: .: lower 4 wander, for example: phenyl, Zheng tolyl, m-toluene, base, pair: '. ' - · ; · · : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : /丨:: '-· .····.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . The indene fused ring hydrocarbon group is not limited to the following examples, and may be, for example, 1-naphthyl, .2-naphthyl, indolyl, 2-indenyl, 5-indenyl, 1-phenanthryl, ... - · · - 11 321016 200936567 9-phenanthryl, acenaphthyl, 2_azulenyl, pyrenyl, 2-triphenylenyl. Further, the monovalent ring-collecting hydrocarbon group is preferably a hydrocarbon group having a carbon number of 12 to 18 in the valence ring. Such a monovalent ring-collecting hydrocarbon group is not limited to the following examples, and examples thereof include an o-biphenyl group, a m-biphenyl group, and a p-biphenyl group. Further, the monovalent aliphatic heterocyclic group has a valence of from 3 to 18%. An aliphatic heterocyclic group is preferred. Such a monovalent aliphatic heterocyclic group is not limited to the following examples, and examples thereof include a 2-pyrazolyl group, a 1-piperidinyl group, an N-morpholinyl group and a 2-morpholinyl group. Further, the monovalent aromatic heterocyclic group is preferably a fluorene aromatic heterocyclic group having 2 to 18 carbon atoms. Such a monovalent aromatic heterocyclic group is not limited to the following examples, and examples thereof include a bis(a)-based group, a 3-indenyl group (〇xadiaZ〇lyl), a 2-°-folly-based group, and a 3-sigma-based group. Base, 2-nonyl, 3-thinyl, 1-°-l-loryl, 2-rpyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-well Base, 2-oxazolyl, 3-isoxazolyl, 2-thiasallyl, 3-isothiazolyl, 2-imidazolyl, 3-pyrazolyl, 2-quinolinyl , 3-啥琳基, 4-啥淋基, 5-wow Linky, 6-啥琳基, 7-喧琳基, 8-喧lin, 1-isoline, 2-purine (quinoxalinyl), 2-benzopyranyl, 2-benzononenyl, N-indolyl, indolyl, N-° octagonal, NW acridinyl, 2-M phenyl, 3-phenylene, hydrazine 1*, and phenanthrolyl. Further, the alkoxy group is preferably an alkoxy group having 1 to 8 carbon atoms. The alkoxy group is not limited to the following examples, and examples thereof include a decyloxy group, an ethoxy group, a propoxy group, a butoxy group, a tertiary butoxy group, an octyloxy group, and a tertiary octyloxy group. 12 321016 200936567 . . . In addition, the aryloxy group is preferably an aryloxy group having 6 to 14 carbon atoms. Such a fang·' . . . r. oxy group is not limited. The following examples are given, for example: phenoxy, 4-tri-silt-butyl phenoxy, 1-naphthyloxy, .2-Naphthyloxy, 9-decyloxy. In addition, the alkylthio group is preferably an alkylthio group having 1 to 8 carbon atoms. Such alkane; ' . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Sulfur based. Wide: ...... .. - In addition, the arylthio group is an arylthio group having 6 to 14 carbon atoms. Such a fragrance........................... The sulfur group is not limited to the following examples: %, for example: phenylthio, 2-toxin benzene sulfur Base, 4-tertiary butyl phenylthio group. Further, the substituted amine group is preferably a substituted amino group having 2 to 26 carbon atoms. Such a substituted amine group is not limited to the example of ruthenium, and may be exemplified by: methylamino group /, ..... . . . . . -; . J-ethylamino group, hydrazine, hydrazine-diethyl Amino group, hydrazine, hydrazine-diisopropylamino group, :N:, - · : amine group, N-cold methylamino group, Ί^Ν-丄(:benzyl group) by base: : 乂 (ylamino, Ν-phenylmethyl culvert vN, :N-di: phenylamine: amide, hydrazine, Ν-bis-* ^ ^ . ; octyl) amino group:,: N ., .N "Double (p.: phenyl) amine group:, N,: N- interesting (striped base. (0 amino-bis(4-methyl) phenyl) amine plug:, 1 -«-naphthyl-]^phenylamine::: . . . ..... ·.·;. . . : .r : . · /'; : base, Ν-:汊-naphthyl -Ν-phenylamino group.::·' In addition, the fluorenyl group is preferably a ruthenium group having a carbon number of from 2 to 14. Such a ruthenium group does not have a · · · . . . . · · · · Limited to: The following examples can be exemplified by: Ethyl ketone, C 醯 醯 、, 新 醯 醯.: , ' .. :: base, Cyclohexane carbonyl, Benzamidine tomb, Toluene 曱Sulfhydryl, oxime benzoyl,::.'.·, ; 丨.. . . Benzene fluorenyl.:...: In addition, the alkoxycarbonyl group is preferably a calcined carbonyl group having 2 to 14 carbon atoms. The alkoxycarbonyl group is not limited to the following examples, and examples thereof include a methoxy group, an ethoxycarbonyl group, and a benzophenoxycarbonyl group. * . - · · 13 321016. 200936567 The aryloxycarbonyl ginger is preferably a carbon number and an aryloxy group of 2 to 14. Such an aryloxycarbonyl wood is limited to the following examples, and examples thereof include a phenoxy group and a naphthyloxycarbonyl group. Further, the alkane sulfonium tomb is preferably a ruthenium group having a carbon number of from 2 to 14. The alkane sulfhydryl group is not limited to the following examples, and examples thereof include: f sulfonyl group , ' .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . The arylsulfonyl group is not limited to the following examples, and examples thereof include a benzenesulfonyl group, .... . . : p-toluenesulfonyl group. · ... ' · · ' · ''. *· * - · * . * - . , . * . * . * *. * 1 such as 1 to 1 in the range of R1 to R9, alkane hydrocarbon group, aromatic hydrocarbon group, fat. ;- · .. . . , .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . For example: Halogen atom:,: cyano group::, oxime oxy group, aryloxy group, alkyl sulfide; & arylthio group, conjugated amine group, oxime, alkoxycarbonyl aryloxy group, 'Alkane sulfhydryl,: or aromatic sulfonate: 醯基#. Examples of such radix:: ^ ^ . ' V :· . Descriptor: ❹: Factory fan: t 11 Medium: above

..通式.[..23 :…八卜 11. ： 〇12 R16 R15 通式[2]中之纪°至:R16分別獨立地表示氫原子、鹵素原 . .... . . .: : :::. 子、取代或未取代之1價脂肪族烴基、取代或未取代之1:. 價芳香族烴基、取代或未取代之1價脂肪族雜環基、取代 14 321016 200936567 .或未取代之1價芳香族雜ϋ客较 :燒績醯基、或芳嗜遞武t、酿基、號轉基、芳氧祕^ . 通式[幻中之:. .Ar!.▲-、..."r :價芳香槔烴基、或：i價芳香_ ¥雜環基。:_ ::_代或未取我之| .... . .. · · ..... General formula. [..23:...八卜11. : 〇12 R16 R15 Formula [2] to: R16 independently represents a hydrogen atom, a halogen atom, .... . . . ::::. Substituted, substituted or unsubstituted monovalent aliphatic hydrocarbon group, substituted or unsubstituted 1: valent aromatic hydrocarbon group, substituted or unsubstituted monovalent aliphatic heterocyclic group, substituted 14 321016 200936567 . or Unsubstituted 1 valent aromatic scorpion compared to: calcined sulfhydryl, or aromatic philanthropic t, broth, cyclyl, aryloxy. ^ General formula [幻中之:. .Ar!.▲- ,..."r: a valence aromatic hydrocarbon group, or: i-valent aromatic _ ¥ heterocyclic group. :_ ::_ Generation or not taking me | .... . . . · · ...

::子、或1價有被:殘皂ϋ獨表不鸟原子、函素廣 .¾ Γ 此外 ；"·： - 'ΑΓ1 ^ >7 Λ ：., 之r俨朴承乂者可舉㈣♦:丨取玟或未取1代之殘蛛6 ^1θ 、二衣土’更佳者可舉例如：取代或未取代之碳數: 321016 15 200936567 10至18之1價芳香轉烴基 示之取代或未取代之苯基。 通式Μ ν : . - - · -· - · ρ24 再更佳者Μ…通式_·::Child, or 1 price has been: Residual saponin alone, not a bird atom, a wide range of elements. 3⁄4 Γ In addition; "·: - 'ΑΓ1 ^ >7 Λ :., r俨 Park Cheng can be cited (4) ♦: 丨 未 未 未 未 ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ 6 ^ ^ 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 Substituted or unsubstituted phenyl. General formula ν ν : . - - · -· - · ρ24 More preferably Μ...generic _·

'.*' ** ； -； ....... 在此所謂承：我戚未取代之碳'數:6至18:υ _ *:::: Ο 基、及取代或从代之碳數2至4之」價芳』=香族煙 .子、_或未取代之1償脂肪族煙基、取代或未淑、:痛 應_1麵___: :取泰譬奉、烷氧幾基、芳 ^ _醯__:麵^^^^'.*' ** ; -; ....... Here is the so-called: I don't replace the carbon 'number: 6 to 18: υ _ *:::: Ο 、, and replace or replace it Carbon number 2 to 4 "price 芳" = incense smoke. Zi, _ or unsubstituted 1 paying for aliphatic cigarette base, substitution or not,: pain should be _1 ___: take 譬 譬 、, alkane Oxygen group, aryl ^ _醯__: face ^^^^

/.遂式:[2]中之#至俨之較佳去才 ，脂肪族煙基、i :價芳香族如基:.：；]却：炱原f U :以上..’說明關於逋式⑴所示乏夏古上甘'.. f:當以此等具有^ 叙蒸錢製作有機也:元件時，_:EL_/. 遂: [2] in the #至俨's preferred to go, aliphatic cigarette base, i: valence aromatic such as: ::;] However: 炱原 f U : above.. 'Description about 逋The formula (1) shows the lack of summer ancient Gan '.. f: When using this to have the steam to make organic: component, _: EL_

下為“13QQ以下敕佳、更佳、以薦I • . . · · ..--· ' .. - 321016 16 200936567 則依蒸锻法會.有難以製 • ··· ·, · ...... ' ..- •:下特佳。其理由為，若分子量大 作元件之憂。 ... .-.··· . . : 主然而’當依塗稀海製作有機肌元件時，則不受此服。 此時’比起分子量:’更童要的是對於所使用之溶_ 、々鈕 性與塗佈膜之#晶形性。為了容“^ 齊】之洛解 ；：：；^ .會不::’但it不受此代表例所限定。' 〇 321016 17 200936567 :[表 1]: 〇 〇The following is "13QQ or less, better, recommended I. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .... ' ..- •: The next best. The reason is that if the molecular weight is too big for the component. ... .. . . . . . . . . It is not subject to this service. At this time, 'than the molecular weight:' is more about the use of the solution _, the button property and the coating film #晶形. In order to accommodate the "^ Qi" solution; :;^ . Will not::' but it is not limited by this representative example. ' 〇 321016 17 200936567 : [Table 1]: 〇 〇

化合杨 ... .. 化學構造 :: 化《合物 化學構造_ (1) . · . - - .· . (6) _ ... . + ... (2) .·. ..., ..... :.... (7) . '..·· H3^CH3 (3) • .· .·· . • -. ·'.... .... 讓 :顧 '· ··； · • ,* ·-, ..... · (9) :.·. ·· '- (5) (10) Q 18 321016 200936567 Ο ❹ .化合物 化學構造 . - : ... ·.: _化合物 化學構造 • . · . · - .· . • · . . · · ... · . (11) (16) (12) :(Π) m^：\ -昏.· · (13) 丨 ·....· · (18) · ' -； ;：'Λ.； ... . (14) ....... .·. ::，r • - .·- .......- :B9&gt; * . • · · · - . • . ·' .· --. . ...-.. .... -:-,... ·-···.： · ....；, (15) . · · · . _ (20) V ...-· · .·. ·. _ • .. 19 321016 200936567 Ο 化合物 化學構造、 化合物 ,.·....... 化學構造 (21) -. . · .... · ..· - · ... ·. ....... (26) .:: ； :Q (.22) - · .. • .... · . , . . .. · • · _.. ... .. ...... ..... (27) a (23) (28) _PHj g-t^' C24) (财: .- .... . • - ..... -. ：. ； · ' .- .- Λ..…; (25) ···-·. - · (30) ·； . · . ·. - NfEth 20 321016 200936567 ❹ 0 化合物 化學構造 -· 化备物 化學構造 (31) .. ： . · - · · Η3〇ΛΗ3 (36) (32); 麵: ：-&lt; - ；.· · · ·. (37) -· · (33) .-,· .·',·· . · . Η3(Τ\__ (38) ' ' · . • · (34) (•39) • · . . - · . · (# • · · · v ·... HsV：hs . - -； 剌 21 321016 200936567 化合物 化學構造 • · . - ·- .- . 化合物 化學構造 (41) . - . (46) .. (42) ...... . . . ' . · · .. . . . - &quot; . · · .... (47) « ηΛλη, V .. (48) (44) ... ' . .· - · . · . .- (49) j ....... ,· -· :(45) ::辱 (50) Q v 〇 ... .. . .· .^):本發明之具有咔唑基之化合物可使用於各種用ιέ。例 • ..... , .. ... ··. .·..···.·. 如：可傲為顯現增感k果、發熱效果、顯色效桌、褪色效 果、蓄光效果、相變化效果、光電轉換效果、磁光效果、 光觸媒效果、光調變效来、光記錄效果、自由基產生效果 ；. . 22 321016 200936567 . . · * .,.- •等機能之材:料;或相反地做為接受此等效果而具有發光機 能之甘料使甩。果具體也可舉例如：杳光材料、光電轉換 材料、光記錄材料'影旅形成材料、先致變色(ph〇 t 〇chr〇mi c) 材料、有機EL ##、光:電等材料、二色婊材料、自由基產 .生f料、鰊產生材料:、:驗產圭材料、蓄先材料、.非鍊形光 學材料、二攻諸波產生封料、三次諧波^生材料、感光材 料:、光吸收材料、泌紅外光殊收材料、·b學燒淘 〇 (photochemical hole, b §己材科、.光^ ^ :轉ϋ紀錄材料.、声為耙鱗材科、光動力療法用色素筝t 此等上赛所屬之卷多用考中，:以做為#機EL材料(貪 ::感EL甩材料、有機EL元件用材料耽 :::當做辱#機苺元家用献料像再等誇，替別妾来#料豸 '精翼—再結♦勢'每沉殿法〔、區帶參化(z〇ne 中尤以依#結晶法為备V在具有昇華性之也舍心乏楱形 J1 :以較目禪化合舞之昇華溫度更低溢維持昇華皿ι而預先去 除所破昇華之不純鉍之方法^此外，期望對採集昇華物之: 部分施予溫度榉库养昇華妹分散在不純物與目標物之方巧 進行。如上述之昇華精製係如將不純物分離之精製，而爲 可使用於本煢明者。此外，經由進行昇.華精製，而有助於 預測材料之蒸鍍性之難易度《» , · 23 321016 200936567 β , : :- 在此，詳細說明關於可使用本發明之具有咔唑基之化 物所製作之有機EL:元#: ^ 有機EL·元件俦由在腸植與陰極間形咸一展或声層有 痛層之元件所樽成〜在此::，所謂二層型有機虹元件，係指 在陽極與陰銲間僅由杳今層紅成之元件。另一方面，所謂 J層型有爽呌元件，係指除了弩光層以外，為了使電洞或: :電予容易注八至發光層、:歲使在發光層内:乏電洞與電子之 〇再結合順碌進行之目的ν而積層有電洞注入層、電洞輪送 層、電洞阻播層、電子注八:層等者。因」心 ::、元件之$斤表性:之元 :::元羡構成:CO ^ ^ 極〆電巧洋入層；/電洞輸送層/發光身^/陰極^乂幻嗓族/ 释光層電黃輪送雇/陰柽，(；4)考極:/電洞 ::年士層土零悬命送層光等/畲子注乂聲4*極、爾 .陽Μ /意柯咸入層;/聲光'層^/電巧血喪層y電芋注入層 .,:阻律層〆電手注入層/琀極、(7)暢:拯/發光層/電洞阻撐 :層/電于:注入層/陰極、(8)暢極/發光層2電子注入層〆 陰極等-:。二:::: .... .. · - ..· ,. · .· . -. . · .-· -,.·.. 此外’上域之各;有機層可务.別由兩層以上之層構成戶斤 形成’也可;重複屬積數層^如此，之例孚，近年來，為了择 :兩光取出致率’雨有將上述之多層型有機EL元件之一部分: 冬層夕層化&lt;稱為「多光子發射（multi photon emission)」 之元件構成之择案。此係在例如由玻璃基板/陽極/電洞 - ' . . ' ^ 321016 200936567 •輸送層/電子輸送性發光層/電子注入層/電抒產生^ :構成之有機虹元件“ .產生層與發光單元之部分。..〈设歡層&amp;了 本發明之具有料墓有機虹:元件甩材料) 卜’本叙明之有機EL#件用材料當然可使用單一外厶私 ::就亦轉行混合、錄 〇:詹'響 效果1且_成與陽極界翁性而 ；；;：^ ^γ1像用夤材料稱為電洞注入料七給m,: 、乏有機£[元輊爾: '杜電输送材科 。材電调輸送:: 调遷·α〇Ιβ議气材料峡洞鶴材必· ::V、 ，且游離_常為5 也^ ::之低游離能:。:如此之電洞注入層以可以敕低的番七 :::_輸:送至發光層之‘佳、電^ 佳。可▲太絡日曰+ 士 k ’乂爲 cm /y:·秒者為 1篇5魏__辨_其_: 之電荷輪送材料所慣用者方面做為電洞 茶Λ和有機£Ltg件之電洞注入層中 200936567 . .. ,· -所使用之習知物中遂擇柱意者使用。 做為如弗之電洞注入材料和電洞輪遂材料不限定於以 下之:例子’可舉例如：:；唑衍生物（參照美國專利311219了 號說明書等)、嗓二唑衍矣物(美國專利3189447號說明書 :等)、味唾衍生物(#照日本特公昭:37、16()96號公報等〉^ •:聚芳基燒街生物（參照美國專剥36154〇2號說明書，美國專 利382_號說明書，美風專利3 〇錢昭45-555號鱗轉^ ^ ^ 51-9a224 ，a ^ 55-17105 , ::報，林贿㈣ J本特開、昭55_8δ〇64號公破)，: 似 ::W，自太i ng 办?|讀本特_49 一 _ 輕41號兮報’日本特殊賠57_45 ς丄 :瞧卿Τ號公報，日:本特_ 公昭51-101仍號公報，日本特公胪^: Λ个竹 胜八η&gt; σ 46〜3712號公報，汨^ :特公昭47-2533:6號公報，日本^pw :v厂 ^ R 士姓Μ π„ 厂 尽特開埤54一53435號公報， 曰本特開昭54-110536號公報，日…' 公報尊）、芳基胺衍生物_專昭5_概^ 美國專利第318〇m號說明查，美茂67450號說明書， 母美國專利第3240597號說 321016 26 200936567 明書，美國專利第3658520號說明書，美國專利第4232103 號說明書，美國.專利第.4175961號說明書，美國專利第 - · - . . . - - ； ... 4012376號說明書，日本特公昭49-3570.2號公報，a本特 -· . - . ' ·. . .... . · . - · 公昭39-27577號公報，.日本特開昭55-144250號公報，日 ' · · - . . · · - · . - · · · 本特開昭56-119132號公報，日本特開昭56-22437號公 報，西德專利第1U0518號説明書等）、胺基取代查酮 • · . . . .' - ... 〇 (chalcone)衍生物（參照美國專利第352650.1號說明書 等）:、Π§唑衍座物&lt;美國專利第3257203號說明書等中所揭 示者）、.笨乙烯墓落衍生物(參照日本特開昭56-46234號会 報等）、苐酮街生物（參照日本特開昭54-110837號公報 :等:)、腙（hydraz0ne)衍生物(參照美観專利第3Τ17462號說 • . - ’ _. ... - · · . · · . -· . · :明書，日本特開昭M-59143號公報，丑本特開昭55-52063 • - . · . - ·-..·· . · - ； · · ... · - - · .··' ';' -. &quot; 號公報，日:本特開昭55-52064號公教，日本特開昭55- ‘ :46760號公翁V?日本特開昭55-85495號公報，日:糸特開昭 57-11350號公報，日本特開昭57-148749號公報，日本特 ❹開平2-311591號公報等)、二苯么烯衍生物(參照:日本#開:: 昭61-210363號公敎，:日本特開昭61-228451號公報，::日） .· . . 本特開昭61-14642號公報’ S本特開昭61-72255號公報，. .. · . . ........ . ........ ... .. ... · · . . 日本特開昭62-47646號公報，日本特開昭62-36674號公: 報，Η本特開昭62-10652號公報，日本特開昭62-30255 ...... ·. ·. . · · · 號公報，日本特開昭60-93455號公韻：;日本特開昭60- • ... · · .... .· , 94462號公報，日本特開昭60-174749號公報，日本特騎 昭60-175052號公報等)、矽氮烧衍生物(美國專利第 - ... 49509:50號說明書)、聚矽烷系（日本特開平2-204996號公 27 321016 200936567 • - 二報）、苯胺系共聚物（日本特開乎2__2δ2263號公報)、日本 :特開平:1 -21 i399號公報中所银n導電性高分子寡聚物 (特別是嘍吩寡聚物）等: * . _ · — ‘ . 並且，:電洞注入材料和電_送材料可舉例如：卟琳: (porphyrin)化合物（B本特開昭63一29咖 香族三級胺化舍物及苯乙稀胺化合·(參照美國專=Chemical Yang... Chemical structure:: Chemical composition _ (1) . · . - - . . . (6) _ ... . + ... (2) ..... , ..... :.... (7) . '..·· H3^CH3 (3) • .· .·· . • -. ·'.... .... Let: Gu · ··; · • , * ·-, ..... · (9) :.·. ·· '- (5) (10) Q 18 321016 200936567 Ο ❹ .Chemical construction of compounds. - : ... ·.: _Chemical Structure of Compounds · · · · · ··································································· 13) 丨·....· · (18) · ' -; ;:'Λ.; ... . (14) ....... .. ::,r • - .·- . ......- :B9&gt; * . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .: · ....;, (15) . · · · . _ (20) V ...-· · ··· ·. _ • .. 19 321016 200936567 化合物 Chemical composition of compounds, compounds, .. ... Chemical Structure (21) -. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . - · .. • .... · . , . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ^' C24) (财: .- .... . • - .. ... -. :. ; · ' .- .- Λ.....; (25) ···-·. - · (30) ·; · · · · · - NfEth 20 321016 200936567 ❹ 0 Compound chemical structure -· Chemical composition of chemical preparations (31) .. : . · · · · Η3〇ΛΗ3 (36) (32); Face: :-&lt;-;.· · · ·. (37) -· · (33 ) .-,· .·',··· . . . Η3(Τ\__ (38) ' ' · . • · (34) (•39) • · . . - · · · · (# • · · · v ·... HsV:hs . - -; 剌21 321016 200936567 Chemical Structure of Compounds · · - - - .- . Chemical Structure of Compounds (41) . - . (46) .. (42) ...... . . . ' . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . - (49) j ....... , · -· : (45) ::Insult (50) Q v 〇... . . . . . . . . . Can be used in a variety of uses. Example • ..... , .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 如 可 可 可 可 可 可 可 增 增 增 增 增 增 增 增 增 增 k k k k k k k k k k k , phase change effect, photoelectric conversion effect, magneto-optical effect, photocatalytic effect, light modulation effect, optical recording effect, free radical generation effect; . . 22 321016 200936567 . . . * .,.- • Other functional materials: Material; or conversely, as a result of receiving such effects, it has the function of luminescence. Specifically, for example, a calendering material, a photoelectric conversion material, an optical recording material, a film forming material, a first color change (ph〇t 〇chr〇mi c) material, an organic EL ##, a light: electricity, and the like, Bicolor enamel material, free radical production, raw material f, bismuth production material:,: inspection of raw materials, storage materials, non-chain optical materials, two-wave generation of sealing materials, third harmonics, raw materials, Photosensitive materials: light absorbing materials, secreted infrared light-receiving materials, b-lighting and polishing (photochemical hole, b § 己材科, .光^ ^: change of record materials., sound for 耙 材 科, light Color therapy for the use of coloring kite t This is a multi-purpose test of the volume of the game, as: #机EL material (greed:: EL 甩 materials, materials for organic EL components :::: as a shame #机莓元家用The content of the offering is like a boast, and it is not necessary for the 豸 豸 豸 精 精 精 精 精 精 精 精 精 精 精 精 精 精 精 精 精 精 每 每 每 每 每 每 每 每 每 每 每 每 每 每 每 每 每 每 每 每 每 每Sexuality is also lacking in shape J1: the method of lowering the temperature of the sublimation of the meditation and dancing, maintaining the sublimation of the dish and pre-removing the impureness of the sublimation The Chinese material: Partially applied to the temperature, the literacy of the sublimation is dispersed in the impure object and the target. The sublimation refining system as described above is refined for the separation of the impurities, and can be used for the present invention. Carrying out the refining and refining, and helping to predict the evaporability of the material. "» , · 23 321016 200936567 β , : :- Here, the details are made regarding the carbazole-based compound which can be used in the present invention. Organic EL: Yuan#: ^ Organic EL·Component 樽 is made up of components that form a salty joint between the intestine and the cathode or a painful layer of the sound layer~ Here::, the so-called two-layer organic rainbow element, Refers to the element that is only red in the anode and the cathode between the anode and the cathode. On the other hand, the so-called J layer type has a refreshing element, which means that in addition to the calendering layer, in order to make the hole or: To the luminescent layer, the age is in the luminescent layer: the lack of holes and the electrons are combined with the purpose of smoothing. The layer has a hole injection layer, a hole transport layer, a hole blocking layer, and an electron note eight. : Layers, etc. Because of "heart::, the weight of the component: the yuan::: yuan 羡 composition: CO ^ ^ Ocean into the layer; / hole transport layer / luminous body ^ / cathode ^ 乂 嗓 / / luminescence layer electric yellow wheel to send hire / haze, (; 4) test pole: / hole:: 士士层土零Suspension of the layer of light, etc. / 畲 乂 4 4 4 4 4 4 4 4 4 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意 意〆Electric hand injection layer / bungee, (7) smooth: Zheng / luminescent layer / hole resistance support: layer / electricity in: injection layer / cathode, (8) smooth / luminescent layer 2 electron injection layer 〆 cathode - :. 2:::: .... .. · - ..· ,. · .. . -. . · .-· -,..... In addition to the 'upper domain; organic layer can be. It is possible to form a layer of two or more layers. It is also possible to repeat the number of layers. In recent years, in order to select: two light extraction rates, the rain has a part of the above-mentioned multilayer organic EL element. : Winter layering &lt; The choice of components called "multi photon emission". This is for example produced by a glass substrate / anode / hole - ' . . ' ^ 321016 200936567 • transport layer / electron transporting light-emitting layer / electron injection layer / electricity generation ^: composed of organic rainbow elements ". Generate layer and light Part of the unit.. <Setting layer &amp; the material of the tomb of the present invention: the element 甩 material) The material of the organic EL# piece of the present description can of course use a single outer smuggling:: Recording: Zhan's sound effect 1 and _ into the anode and the end of the line;;;: ^ ^ γ1 like the use of enamel material called hole injection material seven to m,:, lack of organic £ [Yuan Muer: ' Duo Electric Transport Materials. Material Electric Transfer:: Transfer · α〇Ιβ Discussion Material Xiadong Crane Material · ::V, and free _ often 5 also ^ :: low free energy: .: So The hole injection layer can be reduced to the lower seven:::_: the 'good, electric ^ good to the luminescent layer. ▲ 络 络 曰 + 士 k '乂 is cm / y: · second is 1 5 Wei __ _ _ _: The charge of the material of the wheel is used as a hole in the hole injection layer of the electric hole tea and the organic £Ltg piece 200936567 . . . , · - the used things Use it in the middle of the column. The hole injection material and the hole rim material are not limited to the following examples: Examples include: azole derivatives (refer to US Patent No. 311219, etc.), oxadiazole derivatives (US Patent 3,189,447) No. specification: etc., taste saliva derivative (# according to Japanese special public Zhao: 37, 16 () 96, etc. ^): Polyaryl burning street creatures (refer to the US special stripping 36154〇2 manual, US patent 382 _# manual, US style patent 3 〇钱昭45-555 scales turn ^ ^ ^ 51-9a224, a ^ 55-17105, :: newspaper, bribe (four) J Bent open, Zhao 55_8 δ 〇 64, broken) : Like::W, from too i ng to do?|Read Bent _49 a _ light 41 兮 report 'Japan special compensation 57_45 ς丄: 瞧 Τ Τ 公报, day: Bent _ Gong Zhao 51-101 still bulletin , Japanese special public 胪 ^: Λ a bamboo wins eight η &gt; σ 46~3712 bulletin, 汨 ^: special public Zhao 47-2533: No. 6 bulletin, Japan ^pw: v factory ^ R 士姓Μ π„ Factory end Kaikai No. 54-53435, 曰本特开昭54-110536, Japanese... 'Zhong Zun Zun', arylamine derivatives _ special 5 _ ^ ^ US Patent No. 318 〇 m number description, Mei Mao Manual No. 67450, Mother Beauty U.S. Patent No. 3,240, 597, issued to the United States Patent No. 3, 025, </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; Japanese Patent Publication No. 4012376, Japanese Patent Publication No. 49-3570.2, a Bent-·. - . ' . . . . . . . . . . . . . . . . . . .公告, ' · 56 56 56-119132, Japanese Patent Laid-Open No. 56-22437, West German Patent No. 1U0518, etc., amine Substituted ketones · · . . . - - 〇 (chalcone) derivatives (refer to the specification of U.S. Patent No. 352650.1, etc.): Π § azole flavonoids &lt; US Patent No. 3257203, etc. The revealer), the stupid vinyl tomb derivative (refer to Japanese Unexamined Patent Publication No. 56-46234, etc.), the ketone street creature (refer to Japanese Patent Laid-Open No. 54-110837: et al.), 腙(hydraz0ne) derivative (refer to the US Patent No. 3, No. 17462). - ' _. ... - · · · · · · -· · · : Mingshu, Japan Bulletin No. M-59143, Ugly, JP-A-55-52063 • -. · ······················· ' ' ; Bulletin, Japanese: Benedictine No. 55-52064, Japan, JP-A-55-': 46760, V. V. Japan, JP-A-55-85495, Japan: 糸特开昭 57-11350 Japanese Patent Publication No. Sho 57-148749, JP-A-2-311591, etc., and dibenzomene derivatives (Reference: Japan #开:: Show No. 61-210363, Japan: Special Open Japanese Patent Publication No. Sho 61-228451, :: Japanese) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Japanese Gazette No. 10652, Japanese Special Report No. 62-30255 ...... · · · · · · · Bulletin, Japanese Special Open No. 60-93455 Gong Yun:; Japan Special Open 60- • ... - 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 No. 50 Specification), polydecane system (Japanese Patent Laid-Open No. 2-204996, No. 27 321016 200936567 • - Second Report), aniline copolymer (Japanese Patent Publication No. 2__2δ2263), Japan: Special Kaiping: 1-21, No. Silver n-conductive polymer oligomer (especially porphin oligomer): *. _ · - ' . Also, the hole injection material and the electricity-feeding material may be, for example, 卟 :: (porphyrin) Compound (B) special open Zhao 63-29 coffee fragrant three-stage amination and styrene amine combination (refer to the United States =

4127412^^^^, a ^ 03 53^27033 , Q 各開昭54-58445號公報，日.本貧_ :日本特開昭㈣機 公報，日本特開咕61—2955耶號公報Γ曰太姓: ^4127412^^^^, a ^ 03 53^27033 , Q Kaikai No. 54-58445, Japanese. This poor _: Japanese special open (four) machine bulletin, Japan special open 咕 61-2955 yeah Γ曰 too Last name: ^

^ V 1日本特開昭61-9835V 么報，日本.特.開昭63-:號公報等 办:? ·日本麵平4-3_8.號雜，所記棄之三藉坡 3 職:_(starb_i成，· 舉絲基)三苯轉等。欺，:魏^ ::無_麵基議 . ...·... * . ·.. . ·.·.....-: · - , · · ... -·.·.. ' - ：；；^ nτ^, 二4 4， 'N，N —二革基'N，r~(3、甲基苯基H，r-聯苯 ，—鞍：N，N，N’，r-(4—甲基苯基）一 lu 321016 28 200936567 • . . ..- . • · - ,.- . :二胺、N，.N，N’，N’ -(4-甲基苯基)-1, Γ-聯苯-4, 4’ -二胺、 . ... . ... .… · ·. :Ν, Ν’ -二苯基-Ν，Ν’ -二萘基-1，1’ -聯苯-4, 4’ -二胺、 N，N，-(甲基苯基)-N:，N，-(4-正丁基苯基）-菲-9, 10-二胺、 N，N-雙（4-二-4-甲苯基胺基苯基&gt;-4-苯基-環己健&lt;、Ν，Ν’ - • ' - . , . - ... 雙（4’ -二苯基胺基-4-聯苯基)-Ν，Ν’ -二苯基聯苯胺、Ν，Ν’ - . ' . ... '： ..；.· · .雙(4’ -二苯基胺基-4-苯基)-Ν，Ν’-二苯基聯苯胺、:Ν，Ν’ , .· .... · 雙（4,-二苯基胺基-4-苯基)-Ν，Ν’ -二(1-萘基）聯苯胺:.、 Ν，Ν’ -雙（4’ -苯基(1-萘基）胺基-4-苯基)-N, IT-二苯基聯 . . - 苯胺、Ν，Ν’ -雙（4,一苯基(1-萘基）胺基-4-苯ί)-,Ν，Ν’ -二 . . .... ..... ·'.·'·· ···-.. ... (1-萘基）聯笨胺參。此等可使用於電洞注入材料、電洞輪 . . .... . . ：. . · ·· · ·'.&quot;· .· ... '; “ ... ·· · - · ' ·' · · ..... - ·、. :送材料任一者:。.:一: :電洞注入材料之特隹例如表2所示。 〇 29 321016 200936567 Ο ❹ 化合物 化學構造.,:.. 化合物 化學構造 &gt;λΡ R-o Ο-P S^〇 HI Ml ' ' : BIM6 ΗI M2 o-v&quot; V • . HIM7 〇·^ξ : : ΗI M3 HIM8 HIM4 ,. . ·：.... HIM9 ... . * .....· .. ::p f 5 O . . .... . ·· .·. , ..... ·.. . - • · - ·· • · · .- · · ...... .··. · ' . HIM5 -. . - .... .. -· .. . . · . ... .- 此外，可與本發明之化合物(有機EL元件用材料)一起 - &quot; ·. · . . · .·... ·· ... ..‘ · · .· · -.- . . - 使用之電洞輪送材料也可舉例如下述表示3所示之化合 '- ； ; ..... : 1 -.' - · ' · ' ' ... ... : . •LL· ' · m ° 30 321016 200936567 -[表 3] 化合物 .· . -. :: 化學構造 化舍物 &amp;學構造… HTM1 ::警_ ΗΤΜ5 _ Ρ- Q _ ::感 ύΎλύ HT.M2 ::' ΗΤΜ6 • ... ... :麵：: 心：:^ HTM3 ΗΤΜ7 ： Ο Q HTM4 :七石:: ... '，. ΗΤΜ8 :霸 Ο ο :在形威以上所說明之電洞注入層時，係將上述之&amp;合 . · · ·. - · ··.' 物fe例如真空蒸鍍法、旋轉塗佈法、洗鑄法、LB(Langmuir- . ··.·.·. · - ·. · · · ·^ V 1 Japan Special Open 61-9835V 报报, Japan. Special. Kai Zhao 63-: Bulletin, etc.: · · Japanese noodle 4-3_8. No. Miscellaneous, the three abandoned by the three slopes: _ (starb_i into, · lift silk base) triphenyl to turn. Bullying, Wei: :: No _ surface basis. .......... * . ·.. . ·......-: · -, · · ... -·... ' - :;;^ nτ^, 二 4 4, 'N,N —二革基'N,r~(3,methylphenyl H,r-biphenyl,-saddle: N,N,N', R-(4-methylphenyl)-lu 321016 28 200936567 • . . . . . . . . . . , . . . . : Diamine, N,.N,N',N' -(4-methylbenzene -1, Γ-biphenyl-4,4'-diamine, . . . . . . . . . . : : : : : , , , , , , , , , , , , , , , , 1,1'-biphenyl-4,4'-diamine, N,N,-(methylphenyl)-N:,N,-(4-n-butylphenyl)-phenanthrene-9, 10- Diamine, N,N-bis(4-di-4-methylaminophenyl)&gt;-4-phenyl-cyclohexene&lt;,Ν,Ν' - • '- . , . - ... Bis(4'-diphenylamino-4-biphenyl)-indole, Ν'-diphenylbenzidine, anthracene, Ν' - . ' . . '::..;.· · . (4'-Diphenylamino-4-phenyl)-indole, Ν'-diphenylbenzidine, Ν, Ν', .. .... · bis(4,-diphenylamino) -4-phenyl)-indole, Ν'-bis(1-naphthyl)benzidine: ., Ν, Ν'-bis(4'-phenyl(1-naphthyl)amino-4-phenyl) -N, I T-diphenyl-linked. - Aniline, anthracene, Ν'-bis(4,1-phenyl(1-naphthyl)amino-4-phenyl)-, Ν, Ν'-II. ..... ·'.·'·····-.. ... (1-naphthyl)-linked sulfhydryl ginseng. These can be used for hole injection materials, electric wheel wheels. . . . .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Either: ..: one: : The characteristics of the hole injection material are shown in Table 2. 〇29 321016 200936567 Ο ❹ Chemical structure of the compound.,:.. Chemical structure of the compound>λΡ Ro Ο-PS^〇HI Ml ' ' : BIM6 ΗI M2 o-v&quot; V • . HIM7 〇·^ξ : : ΗI M3 HIM8 HIM4 ,. . ·:.... HIM9 ... . * .....· .. :: Pf 5 O . . . . . ················································ HIM5 -. . - .... .. -· . . . . . . . . - In addition, together with the compound of the present invention (material for organic EL elements) - &quot; · · · · · .····· . . . . . . . . . . . . . . . . - - - - - - - - - - - - - - - - - - - - - - - - - - - - - ; ; ..... : 1 -.' - · ' · ' ' ... : : • LL· ' · m ° 30 321016 200936567 - [Table 3] Compounds.· . -. :: Chemistry Structured &amp; Structure... HTM1 :: Police _ ΗΤΜ5 _ Ρ- Q _ :: ύΎλύΎ HT.M2 ::' ΗΤΜ6 • ... : : : :: Heart::^ HTM3 ΗΤΜ7 : Ο Q HTM4 : Seven Stones:: ... ',. ΗΤΜ8: Hegemony ο : When the hole injection layer described above is used, the above will be combined with the above. · · ·. - · ··.' For example, vacuum evaporation method, spin coating method, washing method, LB (Langmuir-. . . . . . . . . . .

Modgett)法等習知方法而形成薄膜。電洞注入層之膜厚無 特別限制，通常為5nm至5 //111。 另一方面，在電子注入層中，係使用對於發光層顳示 .广: . - 優良之電子注入效果，且可形成與陰極界面之密著性與薄 . · · - '·. ·. ·- .. . .. ..· . · -• . ... . , ... - '31 321016 200936567 - 令 + . + 昏· _ , . -膜形成性優良尤電子注入層之電子注入材料。如此之電子 注入材料不限定於以下之例子，可舉例如：金屬錯合物、 含氮五員環衍生物、苐酮衍生物、蕙酿二甲烧衍生物、聯 . · ; · 苯醌衍生物、嗟鳴(iMopyran)二氧化物衍生物、花四甲酸 ... ' ;· ........ ' . ... . . :衍生物、亞第基ΐ烷衍生扁、蒽酮衍生物、矽雜環戊二婦 . · ,·· · · · :(si 1 〇1 e)衍生物、三芳基膦氧化物街差物、乙.醯乙酸舞、 ... - _ ' 乙酸鈉彳此外’也可奉例如::將銘等金屬摻雜至二.苯基啡 • .· · ... /·. .... ❹琳（bathophenairthroline)中而成之無機/有翁複合材料 (高分子學會預锖稿集，第50卷，4號;，660頁，, 2001年 . · .· ... ^ . 二:::黄行)、或:「 :稿集，N0· 3, !4〇2、頁，2卿年杳行」中搿乾载之 )薄膜-’並轉夂來自陰赛之電子，且寸輸送電手之材料，則: :.ϊ.不受:此孝特別被:定: . . ·· ·. . . ·. .·,：·；.·. ^ ·.- ··-.··.·. ：. · -·-：·. :舞物、含氮革員環衍 氧化物衍生物。： 舞的余屬舞合物▼舉例如I—舉基啥琳或其衍生鲮 广之余屬錯合物。8-羥基喳啉或其:衍差物之全屬錯合物之具 ::體钶不限定於以下之例手，可譽例如:參Ο—幾基喳啉)鋁^ 4(2-甲基本齡轉)銘、參 參（5-甲基-8-經基輕）紹、參(5_笨基—8_羥基喹•麵、： 雙(8-幾基喳啉&gt;(1—萘酚)銘、雙（8_羥基喹啉）(2_萘酚） 鋁、雙 - -. ·..··. . • . . · . . . · . - · 321016 32 - 200936567 萘酚)鋁、雙（4-甲基-8-羥基嘻琳）（1-萘酚）鋁、雙（5-甲基 * . -8-裡基唆琳）（2-萘盼.)铭、雙_(5-苯基-.8~幾基ϋ奎來）（苯齡)_ 銘、雙（.5-氰基—8-幾.基啥琳）（4-氨基-1-萘驗）紹、雙.(8- • ... . ....... · ... · ; · · 羥基喹啉）氯鋁、雙（8-羥基喹啉）（鄰甲輪）鋁等鋁錯合物; . ： . ... . ..... 參（8-巍基喧琳）鎵、參（2-曱基-8-幾基嗟琳)鎵、參(4-甲 • , - ； . - . .... · . © 基-8-經基嗟琳）鎵、參（5-甲基-8-經基啥咏）鎵、參（2-甲 基-5-苯基-8-羥基喹啉)鎵、雙（2-甲基-8-羥基喹啉）（1-萘酚)鎵、雙(2-甲基-8-羥基喳咻）（2-萘餘)鎵、雙（2-甲基 -8-羥基喹啉&gt;(苯酿)鎵、雙(2-曱基-8-羥基喹啉）（4-氰基 • ' · ' -1-萘酚）鎵、雙（2,4-二甲基-8-羥基喹啉)(1-萘輪)鎵、雙 ...... ........ (2, 5,二曱基-8-羥基喹啉)(2-萘酚)鎵、雙(2-甲墓-5-苯基 -8-羥基喹琳）(苯酚）鎵、雙(.2-甲基-5-氰基-8-經基喹啉) (4-氰基-1 -萘餘)嫁、雙（2 -甲基-8~輕基σ奎妹)氯森、雙（2-甲基-8-翹基喹(鄰甲酚)鎵等鎵錯合物:；:除腐 有8-輕基啥淋鐘、雙(8-羥基喧淋）銅、雙(8-羧基邊琳)猛、 .. . .. ; .. . ... 〇雙(ία-羥基苯并:[h]喹琳)鈹、雙(8,羥基*啉)鋅:、Κιο- ’· * - · ' . * * . - 雇基苯并[h]喹啉）錚: _ . .· · · . * ..... ： . · · ....- 較隹的含氮五員環衍生物不良定於以下之例子，可舉 , ··.'·. · ...... - · - ·, ·.. ·-.*. .... .. · . · ·； 例如：曙tr坐衍生物、赛4衍生物、卩酵二峻衍生物、嗟二f坐 ：· ' , · . . · · . ' . · . . 衍生物、***衍生物β具體而言可舉例如:2，5 -雙(1 -苯基）: -1，3, 4-噚唑、2, 5-雙(1-笨基）-1，3, 4-噻嗤、2, 5-雙（1， •. --- 苯基）-1，3, 4-卩§二唑、2-(4’ -三級丁基苯基）-5-(4’ ’ -聯苯) -1.，3, 4-嗜二竣、2，5-雙（1_蔡基）-1，3, 4-曙二σ坐、.1，雙 [2-(5-苯基噚二唑基）]苯、l.，4-雙[2-(5-苯基噚二唾基） 33 321016 200936567 --4-三級丁基苯]、2-(4’-三級丁基苯基）-5-(4’聯苯） :-1，3, 4-噻二唑、2, 5-雙（1-萘基)：1，3, 4-噻二唑、.1，4-雙 [2-(5-苯基噻二唑基)]苯、2-(4’ -三級丁基苯基)-5-(4&quot;- . · . ... . . · · - . . . .... · 聯苯）-1，3, 4-三哇.、+2.，5-雙（1-萘基）-'1，3，.: 4—三〇坐·、1，4- . . . . · · . . · ·...· . ..... 雙[2-(5-笨基***基）]苯等。 ...... ·. ... . . .' . 特佳的噚二唑衍生物之具體例如表4所示。: . - · ' - · - .A film is formed by a conventional method such as the Modgett method. The film thickness of the hole injection layer is not particularly limited and is usually 5 nm to 5 //111. On the other hand, in the electron injecting layer, it is used for the light emitting layer. Wide: - excellent electron injecting effect, and can form adhesion and thinness with the cathode interface. · · - '·. ·. - .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Such an electron injecting material is not limited to the following examples, and examples thereof include a metal complex, a nitrogen-containing five-membered ring derivative, an anthrone derivative, a glycerin derivative, and a benzoquinone derivative. , iMopyran dioxide derivative, flower tetracarboxylic acid... ' ;· ........ ' . . . . : derivative, adipyrane derived flat, 蒽Ketone derivatives, fluorene heterocyclopentanol. · , · · · · · :(si 1 〇1 e) derivatives, triarylphosphine oxide street products, B. acetic acid dance, ... - _ ' Sodium acetate 彳In addition, it can also be used as follows:: Doping the metal such as Ming to the second phenyl morphine. . . . . . . . . . . . bat ( (bhophen airthroline) made of inorganic / have Weng Composite Materials (Polymer Society Preview, Vol. 50, No. 4;, 660 pages, 2001. · .. ... ^ . 2::: Huang Xing), or: " : Manuscript, N0 · 3, !4〇2, pp., 2 卿 杳 」 」 」 」 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜 薄膜: This filial piety is specially: set: . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . : Dance was leather membered ring nitrogen-oxide derivatives derivatives. : The surviving dance of the dance ▼, for example, I- 啥 基啥琳 or its derivative 广 之 属 属 。 。 。 。 。 8-hydroxyporphyrin or its derivative of the derivative is: The body is not limited to the following examples, such as: ginseng-several porphyrin) aluminum ^ 4 (2-A Basic age transfer) Ming, Shenshen (5-methyl-8-radio-based light), ginseng (5-stupyl-8-hydroxyquino-face,: bis(8-methyl porphyrin)&gt; Naphthol), bis(8-hydroxyquinoline) (2-naphthol) aluminum, double--....... Aluminum, bis(4-methyl-8-hydroxyindole) (1-naphthol) aluminum, bis(5-methyl*. -8-Ricyl 唆琳) (2-naphthalene.) Ming, double _ (5-phenyl-.8~-singly-based quinone) (benzene age) _ Ming, bis (.5-cyano-8-s. 啥 啥 )) (4-amino-1-naphthalene) Double. (8- • ... . . . . . ; ; · · · · hydroxyquinoline) aluminum chloride, bis (8-hydroxyquinoline) (o-aluminum) aluminum and other aluminum misfit ;; : . . . ..... 参 (8-巍基喧琳) gallium, ginseng (2-mercapto-8-single-base) gallium, ginseng (4-A•, -; . - . . . · . © -8-8-based 镓 )) gallium, ginseng (5-methyl-8-pyridyl) gallium, ginseng (2-methyl-5-phenyl-8 -hydroxyquinoline) gallium, double (2- (8-hydroxyquinoline) (1-naphthol) gallium, bis(2-methyl-8-hydroxyindole) (2-naphthyl) gallium, bis(2-methyl-8-hydroxyquinoline) (Benzene) gallium, bis(2-mercapto-8-hydroxyquinoline) (4-cyano• ' · '-1-naphthol) gallium, bis(2,4-dimethyl-8-hydroxyl Quinoline) (1-naphthalene) gallium, double... (2, 5, dimercapto-8-hydroxyquinoline) (2-naphthol) gallium, double (2-methyl tomb-5-phenyl-8-hydroxyquinoline) (phenol) gallium, bis(.2-methyl-5-cyano-8-pyridylquinoline) (4-cyano-1) Naphthyl), bis(2-methyl-8~light σ 奎 )) chlorosen, bis(2-methyl-8-fluorenyl quinol (o-cresol) gallium and other gallium complexes; Corrosion has 8-light base 啥 钟, bis (8-hydroxy 喧 )) copper, bis (8-carboxy lin lin) fierce, .. . . . . . . . . 〇 ( (ία-hydroxybenzo :[h]Quinline) bismuth, bis(8, hydroxy* porphyrin) zinc:, Κιο- '· * - · ' . * * . - Benzyl benzo[h]quinoline) 铮: _ . . . · . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . - · - ·, ·.. ·-.*. .... .. · · · ·; For example: 曙tr sitting derivative, match 4 derivative卩 二 峻 衍生物 衍生物 衍生物 衍生物 衍生物 衍生物 衍生物 · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · f Phenyl): -1,3,4-carbazole, 2,5-bis(1-styl)-1,3,4-thiazide, 2, 5-bis(1, •. ---phenyl )-1,3,4-卩§ diazole, 2-(4'-tris-butylphenyl)-5-(4' '-biphenyl)-1,3,4-dioxin,2 ,5-double (1_Caiji)-1,3,4-曙2σ sit, .1, bis[2-(5-phenyloxadiazolyl)]benzene, l.,4-double [2 -(5-phenylindoledisal) 33 321016 200936567 --4-tertiary butylbenzene], 2-(4'-tris-butylphenyl)-5-(4'biphenyl) :-1 , 3, 4-thiadiazole, 2, 5-bis(1-naphthyl): 1,3,4-thiadiazole, .1,4-bis[2-(5-phenylthiadiazolyl) Benzene, 2-(4'-tris-butylphenyl)-5-(4&quot;- . . . . . . . . . . . . . . . . 4-三哇.,+2.,5-bis(1-naphthyl)-'1,3,.:4—three-squatting, 1,4-. . . . . . . . .· . . . . Bis[2-(5-phenyltriazolyl)]benzene. .............................. The specific oxadiazole derivatives are shown in Table 4. : . - · ' - · - .

[表4] 化合物 -.-· ' ' \&quot; .. · :::化學構造' 化合物 化學構造 .· . · .· · . EX1 ... ... EI6 ..-..··. • . ：M2：： ： . · :資::¾:八 .-- . ,· ；EX7 -.· · ........· · ··· ·....- . EX3 &gt;c=/ N-N N\ ΈΧ8- • . - . · · _ · EX4 . Q : 0 .EX 9 EX5 Q p x=/ N-N ^ . - · EX 10 34 •321016 200936567 特隹的三嗓衍生物之具體例如表5所示。表5中+',Ph 表示苯基- ' . . ... . &quot;, ' ' * . [表 5} 化合物 化學構造:^ ·. · -· ... ' . ··. · ... .化合物 : 化學構造 '· · · ' ET1 . ： '.... .. · ... • · .. · Ph - .... ·. · • .+....,. . . -. ·-. . . ' ΕΤ6 d : ET2 . .· '. : ..... ΕΤ7 轉。h P . -* - · :ET3 ch3 ...... ΕΤ8 ... - - · . ET4 _謙: N-N 7 ΕΤ9 X=/ N-N ^ - · - • ET5. ' · . ·- ·. · _ · _ - .. ； ΕΤ10 ； •-.- Ph Q V==/ n-n 特佳的矽雑環戊二烯衍生物之具體例如表6&quot;所示。 35 321016 200936567 :[表 6] 化合物 . ··. ... ... :/ 化學構造, 4匕合物 化學構造 ESI ：.. · . Π3^ 1&gt;Π3 ES6 • . . · · .. Q Ο h3c&amp;丨 ch3 ES2 ： .. .... . • ·'-.. ES7 op ES3 .· υ·2Π5 U2n5 ' * .· . * . ES8. .+-.- QQ PP ES4 .· . · ·. rlgU Unj ES9 0 D : .... . . ES5 QQ P0 Tlgw wrlg .... .... ···... - , ES10 ； :分p:匕 :cftfe : 00丨 ::並且，在電;?同阻擔層中，係使用防止通.過發光層之電 . ..: · ' . ;； ... ·.；. . ' . ： 洞到達電子注入層，且可形成薄膜形成性優良之層之電洞 .V -' - ...... . ·' 阻擋材料。如此.之電洞'阻擋材料不限定於以下之例子.，可 舉例如：雙(8-羥基喹啉）（4-苯基苯酚）鋁等铭錯合物、和 雙（2-曱基-8-羥基喹啉）（4-苯基苯鹼）鎵等鎵錯合物、2:，9- 36 321016 200936567 .... -·' . ' .. .. 本發明之有機EL元件之發光層以兼具下述之機能為 • ♦. . ... • ; ， 二甲基-4, 7-二苯基HO-哪啉(BCP)等含焉稠合芳香族化 合物 佳 . · . ' . · . . . ... 注八機熊：在施加電場哼可從陽極或電洞注乂層注人電 .極或電子注入層连入電子之機能 零場之力使所注入之電荷（電子輿電淘）移動 • ' ....... - ....· + . -.. ' ·.. ...... 洞，且可從陰極或電子注入層注.入電子之機能 輸送機能:以…* ‘· 〇 之機能 1 * &lt; ···- ...... ........ 發光機能::提供電子與電洞再結合之場所，f將其與發光 :二連結之機能：. . : · · · . · . ·' · ; ? · - · ' :::::惟，電‘之注入容易i與電子之注乂袁易发可 '.早電洞與電无之移動度所示4輪送能可有大小Λ: : Λ :丨本杳明之化合物適會每:為發光層使用'。特別是適合做 :為製作藍色發1元件之軲耗使甩，:此外，也寸將^發明^ 化舂％旱獨或與其他化:合务鱗合两形戒發先層、:套爽&amp;也 ❹犯合翁缸合時，，本聲明之化合物可為主材料、摻雜劑材辨 或輔助摻雜劑材料之.任―材科。:爲光層由主材磁 '劑材料所形成時.:，重量财主材料:娜 定，59·99至5仏 ^了得到可見祕域(特祕藍色至綠色）之發光、Μ =錄、苯并味峻系'、苯并㈣系等榮光增白劑 化類氧(灿。id^ ： 53-194393 昌不之化合物。並且’其他有用的化合物係列舉於 321016 37 200936567 :Chemistry 〇f S^thetic ])yes(1971)628 至 63Τ 金屬鉗合化類氧化合物可使用例如'日本特賄昭63_ 295695號公報中所揭示之化合物。其代表例可奉例如炎(容― 羥基喹啉)鋁等1羥基喹琳系金屬錯合.物、和二趣表巧哚 ο 此外’前述苯乙烯基苯系化舍物可使用例如：歐洲專 利第0319881號說明書和歐洲專利第〇373¥ ^，a 2-252793 本㈣㈣輕物也可做為發光層之制使:用。'除: 此之科:歐㈣利第。3877成^ 化會物也可傲為發光層之封料使甩。 :二 ;： © 警年))3 驻衍生•㈣特開作 子相關聯合演講會中由以等示謂二讀座 92'220394 _675號公報）、姆并鱗衍 生物（日本特開平2一2卿號公報）、苯乙婦基贿 200936567 (Appl._ Hiys· Lett.，第 56 卷，L799C1990 年））、香豆素 系化合物（日本轉開平2-191694號公報)、如國際專利公報 WO90/13148 :和 Appl·· Phys. Lett.，vol58，18，P1982 (19 91) t所記載之高分子化合物、9，9 ’，1 〇，10 ’ -四笨基 · .冊 - . '.' .. -- · ... - · -2, 2’ -襄蒽、PPV(聚對伸苯基伸乙缚基)衍生物、聚苐衍生 物或此等共杳物。並i，發光層中所使用之具體的化i物 可舉例如具有下述通式]：5]至通式[7]之構造者: Ο 通式[卟靡:^[Table 4] Compound-.-· ' ' \&quot; .. · :::Chemical Structure 'Chemical Structure of Compounds ······ . EX1 ... EI6 ..-..·. • . :M2:: : . · ::::3⁄4:8.-- . ,· ;EX7 -.· · ........· ··· ·....- . EX3 &gt ;c=/ NN N\ ΈΧ8- • . - . · · _ · EX4 . Q : 0 .EX 9 EX5 Q px=/ NN ^ . - · EX 10 34 •321016 200936567 Special three-dimensional derivative specific For example, Table 5 shows. In Table 5, +', Ph represents phenyl-' . . . . . &quot;, ' ' * . [Table 5} Chemical structure of the compound: ^ ·. · -· ... ' . ··· · .. . . compound: chemical structure '· · · ' ET1 . : '.... .. · ... • · .. · Ph - .... ·. · • .+....,. . . -. ·-. . . ' ΕΤ6 d : ET2 . .. '. : ..... ΕΤ7 转. h P . -* - · :ET3 ch3 ...... ΕΤ8 ... - - · . ET4 _ Qian: NN 7 ΕΤ9 X=/ NN ^ - · - • ET5. ' · . ·- ·. · _ · _ - .. ; ΕΤ10 ; •-.- Ph QV==/ nn The specific details of the fluorene cyclopentadiene derivative are shown in Table 6&quot;. 35 321016 200936567 : [Table 6] Compounds · ·· ... ... : / Chemical structure, 4 chemical composition ESI :.. · . Π3^ 1&gt;Π3 ES6 • . . · · .. Q Ο h3c&amp;丨ch3 ES2 : .. .... . • ·'-.. ES7 op ES3 .· υ·2Π5 U2n5 ' * .· . * . ES8. .+-.- QQ PP ES4 .· . · rlgU Unj ES9 0 D : .... . . ES5 QQ P0 Tlgw wrlg .... .... ···... - , ES10 ; : points p:匕:cftfe : 00丨::and In the same resistance layer, the electricity used to prevent the pass-through layer is used. ..: · ' . ;; ... ·.;. . . . : The hole reaches the electron injection layer and can be formed A hole in a layer with excellent film formability. V -' - ... . . . 'Blocking material. The hole-blocking material is not limited to the following examples, and examples thereof include bis(8-hydroxyquinoline)(4-phenylphenol)aluminum and the like, and bis(2-indenyl)- Gallium complex such as 8-hydroxyquinoline) (4-phenylphenyl base) gallium, 2:, 9-36 321016 200936567 .... -·' . ' . . . . . . The layer has the following functions: ♦. . . ; ; , dimethyl-, 4-diphenyl HO-morpholine (BCP) and other fused aromatic compounds are preferred. . . . . . Note: Eight-bear bear: After applying an electric field, it can be injected from the anode or the hole injection layer. The pole or electron injection layer is connected to the function of the zero field of the electron to make the injected charge ( Electronic 舆 淘) Mobile • ' ....... - ....· + . -.. ' ·.. ...... Hole, and can be injected from the cathode or electron injection layer The function of the function of transportation: to ** '· 机 function 1 * &lt; ···- ...... ........ illuminating function:: providing a place where electrons and holes are combined, f The function of connecting it with the light: two:: . . . Yuan may be prone qe 'early mobility of holes with electrically non-transmission of FIG 4 can be the size of Λ:: Λ: Yao Ming Shu present each compound will be adapted: the light emitting layer is used'. Especially suitable for: the production of blue hair 1 component is awkward, in addition, it will also be invented ^ 舂 舂% dry or other: squad squad two-shaped ring first layer, set Shuang &amp; also ❹ 合 合 缸 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , : When the light layer is formed by the main material magnetic material::, the weight of the main material: Nading, 59.99 to 5 仏 ^ to get the visible secret domain (special blue to green), Μ = recorded Benzene-flavored, benzo (4) and other glory brightening agents such as oxygen (can. id^: 53-194393 Chang Buzhi compounds. And 'other useful compounds series cited in 3211037 200936567 :Chemistry 〇f S^thetic])yes (1971) 628 to 63 Τ The metal compounded oxygen-containing compound can be, for example, a compound disclosed in Japanese Patent Publication No. Sho 63-295695. A representative example thereof may be a 1-hydroxyquinoline metal complex such as inflammatory (hydroxy-quinoline) aluminum, and a succinct metal. In addition, the aforementioned styryl benzene compound can be used, for example, in Europe. Patent No. 0319881 and European Patent No. 〇 373 ¥ ^, a 2-252793 (4) (4) Light goods can also be used as a light-emitting layer: use. 'Except: This section: Europe (four) Lidi. 3877 into the chemical can also be proud of the luminescent layer of the seal to make 甩. :二;: © police year)) 3 in the derivative • (4) special open-ended related joint lectures by the equivalent of the second reading seat 92'220394 _675 bulletin), m and scale derivatives (Japan special Kaiping 2 2Qing Pao), Benzene Beneficial Bribery 200936567 (Appl._ Hiys· Lett., Vol. 56, L799C1990), coumarin compounds (Japanese Unexamined Patent Publication No. 2-191694), such as the International Patent Gazette WO90/13148: and polymer compound, 9,9 ', 1 〇, 10 '-four stylyl. . . . -- -- ... - · -2, 2' - 襄蒽, PPV (poly(p-phenylene)) derivatives, polyfluorene derivatives or such conjugates. And i, the specific chemical substance used in the light-emitting layer may, for example, be a structure having the following general formula: 5] to [7]: Ο General formula [卟靡: ^

(式中，R及R分別獨其地表示1償脂肪族煙‘，处表示 3 :至iQQ.之整數) , · ..... · ..... .. ·--. ·. . . . . ·. · - .... ,(In the formula, R and R respectively represent 1 for aliphatic cigarettes, where 3: to the integer of iQQ.), · ..... · ..... .. ·--. ·. . . . .. · - ....

〇 (式中’ R .^R分別彳5立地表示1價脂妨族烴基，㈣及抑 分別獨立地表示3至100.之整數） 通式: . , - ； · . · · ... ·· -；···. . ρΧ5 ρΧβ〇 (wherein R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R R · -;···. . ρΧ5 ρΧβ

(式中，:RX5及RX6分別獨立地表示1價脂肪族煃基，η4及η5 321016 39 200936567 « • - ... .- · · : 分別獨立地表示3至100之整數;Ph奉示苯基)。 此外’也可舉例如：日麥時開平5—258862號公報等中 所記載之通式（Rs-Q)2-A1-0-L3(式中，:L3為令有苯基部分: 而成之碳原亍數&amp;至24個&lt;烴;0~L3爲苯酚配位基；Q表 示取代8-羥基喹淋配位基；Rs表示巧在立體結構上妨礙取 代8-經基嘆淋配位基4秦原子上轉結超過2個之方式選出 之8~羥基喹咩環玫减基）所示之化命物。具體雨言可舉例 ^如：雙（2-甲基-8-氣基奮嚇)(對苯暴苯驗)銘⑴工）、雙(2… ❹曱基-8-羥盖喹琳ΚΙ-萘酚)鋁（III)等。::. · . ·'..·. ' _ ： ....... 得到白色發光時之聲光層無特別限f彳，可使用卞述考:: :,·銳定有激EL積層構造體之各；層之能量辛位:，「利用道造注 入使其發光者（歐洲專利第0390551號公報) ·. · · · · .... · . - . _ · &quot; ... ·· · ::·在同樣利用 &amp;道注十 :實施例者（日未特闕平3_2P邱4號公報丨 : · ^ Μ 2-220390 Μ ^ · 0:報及Ή 本:特開平 2一216790 號公報）:… ...' . -._ ... '' ' : ' . -: : . &quot; .·_ / *' ，將發光展分割成複數層並分别由杳光波1不同乏材科所 ::構成者（日本特後平如5U9l·號公報):y :::.二 * * · * * - . . 令 * . , * * * * , •積層藍色發光雜（螢光波峰380至48〇nm)與綠色發光體 ·.-... ： · · , · . · · - (48〇至58〇·)，再使其含有紅色螢考體而或之構成者〈曰 本特開平6-2071祖號公報)。 •具有藍色發光廣含有藍色螢光色素且綠色發光層含有紅 色螢光色素之區威?再含有綠色螢光體之構成者（a本特開 平7-142169號公報 321016 40 200936567 此等之中 特# i .. ,，以曰本待開平7-142169號公報中所記载者 此外，在本發明之有機EL元件中，可使用磷光發光材 料。此時，本發明之化会物壤合做為發光層中之主材料使 ’係意指在從激發三重態在遷 至基底艇態時發f之彳b舍物。可使用於本發明之有機電激 發光元养4構光發光材料可舉彳列如有機金屬錯合物。有機 © 金屬錯合物:之金屬原子通常為過渡金屬，且較隹的週期為 -· · . . · · 第5遇期或第6週II、:與為β族直族，'更佳為&amp;族至 10族之元章,。具聲两&quot;ί為細或鉑等丨。此外，配位基肴2二 .... , .... ' .... . ... 苯基吼淀或2~&lt;27 -苯并噻吩基)吡唆等'，矣特徵為此等配 位基上之碳厚子與金展:i.接鍵結。另一例可奉例如σ卜你或 ； ： ； ：； '： ： - - ' ^ ； ' &quot; . 四氮雜外^瓖錯合#等’中心金屬可舉例如如等。.例如: ' '： ' - .· ；,.； ： ·.·' ： ·；；：'ν'：· ' . ' -· :下:述所系之習知也合勢遠舍做為麟先番光材料:像(椎，:?h -. 'v ：- ; '： ·；ν ·: ； ' . / - ' ^ ：，' ; '： - . .. Λ ν·ν ' ' ' .,.- 表示.皋墓:)，:飞^ 0 321016 200936567(wherein: RX5 and RX6 independently represent a monovalent aliphatic fluorenyl group, η4 and η5 321016 39 200936567 « • - ... .- · · : respectively represent an integer from 3 to 100; Ph is a benzene base). In addition, the general formula (Rs-Q)2-A1-0-L3 described in Japanese Patent Publication No. Hei 5-258862, etc. (in the formula: L3 is a phenyl moiety: The number of carbon atoms &amp; to 24 &lt;hydrocarbon; 0~L3 is a phenol ligand; Q represents a substituted 8-hydroxyquinone ligand; Rs represents a steric structure that hinders the substitution of 8-thiopyran The chemical substance shown by the 8~hydroxyquinoline ring minus the base selected by the ligand 4 on the Qin atom. Specific rain words can be exemplified ^ such as: bis (2-methyl-8-gas-based intimidation) (for benzene benzene benzene test) Ming (1) work), double (2... ❹曱--8-hydroxy valquinin ΚΙ - Naphthol) aluminum (III) and the like. ::. · . · '..·. ' _ : ....... When the white light is emitted, the sound and light layer is not limited to f彳, and can be used in the following:: :,· Ruiding has an EL layer structure Each of the layers; the energy of the layer: "The use of the road to inject it to make it shine (European Patent No. 0390551) · · · · · .... · . - . _ · &quot; ... ·· · ::· In the same use &amp; Note 10: The example of the person (Japanese Unspecialized Ping 3_2P Qiu 4 Bulletin: · ^ Μ 2-220390 Μ ^ · 0: Report and Ή Ben: Special Kaiping 2 216790 Bulletin):....' . -._ ... '' ' : ' . -: : . &quot; .·_ / *' , splits the luminescence into multiple layers and is different by 杳光波1 Materials Division:: Constructor (Japan's special post as 5U9l· bulletin): y :::. 2 * * · * * - . . . * * , * * * * , • Layered blue glow (Firefly Light peaks 380 to 48 〇 nm) and green illuminators ·.-... : · · · · · · - (48〇 to 58〇·), and then contain the red test body or the composition of <曰本特开平6-2071祖号公告). • Blue light emitting blue fluorescent pigment and green light emitting layer containing red fluorescent pigment District Wei?, which also contains the composition of green phosphors (a, Japanese Patent Laid-Open No. 7-142169, No. 321016 40 200936567, etc.), which is described in the publication of 7-14. Further, in the organic EL device of the present invention, a phosphorescent luminescent material can be used. In this case, the phosphatizing material of the present invention is used as a main material in the luminescent layer, so that the term "system" means moving from the excited triplet state to In the basal state, the organic electroluminescent photoreceptor 4 photoluminescent material can be used as an organic metal complex. Organic © metal complex: metal atom Usually a transition metal, and the period of the helium is -· · · · · · 5th or 6th week II,: and the family of the β family, the 'better is the chapter of the family to the 10th,声声两&quot;ί is fine or platinum, etc. In addition, the coordination base 2 2...., .... ' .... . . phenyl hydrazine or 2~&lt;27 -Benzothiophene)pyridinium, etc., the characteristics of the carbon thickeners on the ligands and gold exhibits: i. bonding. Another example can be, for example, σ卜你或; : ; :; ': : - - ' ^ ; ' &quot; . Four nitrogen For example, ' ': ' - .. ;,.; : ···' : :;;:: 'ν':· ' . ' -· : 下: The familiar knowledge of the system is also a potential material for the Lin Xianfan material: like (Vertebra::?h -. 'v :- ; ': ·; ν ·: ; ' . / - ' ^ : , ' ; ': - . .. Λ ν·ν ' ' ' .,.- Representation. 皋Tomm:),:Fly ^ 0 321016 200936567

42 321016 20093656742 321016 200936567

質以功函數大的（4eV .以上)金屬、合金、導電性化合物或 -......... ....... 上等之混合物為佳。&gt; 此之電:極物質之具鍾例寸舉例如::A mixture of a metal having a large work function (4 eV or more) of a metal, an alloy, a conductive compound or -.......... is preferred. &gt; This electricity: the extremes of the matter, such as:

Au等金屬；CuV、ΙΤ0、Sn〇2、Ζηα等導電性材料。此*陽極 - _ . ' - . . .· · .. 可經由將此等電極物質依蒸鍍&amp;或濺鍍法等方法形成薄膜 • · · . .. - 而得到乂當從陽極取出東自上述發光層之發冕時.，:以令對 ·' ； · .'· _ - -- · · · ··. ... · . .. . ,s. 陽極發光之穿透率大於1鄕為佳。此外，暢極之薄片電阻 以數百Ω /m2以卞著為隹。且，暢極之膜厚雖因材料而 ^ .... ' . :異，但逍常為lOnm至1 // m，且以10至200nm之範圍為隹。 ' ·' . . , ' · -· · . · . 此外，本發明之肴機EL元件之陰極中所使用之電極物 . ' . . . · . · · . . ···.·.· 質以功函數小的（4eV以下）金屬、合金、導電性化合物及 此等之混合物為佳。:. . .... . . ' - 如此之電極物質之具體例可舉例如:細、納•鉀合金、 . .. · -.'·· . · - . · . ..... .· 鎮、鍾、鎮·銀合金、铭/氧化is、is ·鐘合金.、銦、稀土 類金屬等。此陰極可經由將此等電極物質依蒸鏟或濺鍍等 方法形成薄膜而製得。在此，當從陰極取出來自發光層之 43 321016 200936567 零 . * :發光時’以令對陰極發光之穿透率大於10% u以， ' 1極之薄片電阻以备百n 手大於⑽ 4以下者為隹A metal such as Au; a conductive material such as CuV, ΙΤ0, Sn〇2, or Ζηα. This *anode- _ . ' - . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . From the above-mentioned luminescent layer, the radiance of the anode illuminance is greater than 1 It is better. In addition, the smooth sheet resistance is entangled in hundreds of Ω / m2. Moreover, although the film thickness of the smooth film is due to the material, ^.. '. : is different, but the 逍 is often lOnm to 1 // m, and the range of 10 to 200 nm is 隹. ' · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · Metals, alloys, conductive compounds, and mixtures thereof having a small work function (4 eV or less) are preferred. : . . . . . . ' - Specific examples of such an electrode material include, for example, fine, nano-potassium alloys, . . . . . . . . . . . . . . . . . . . . . . . . . . . . . · Town, bell, town · silver alloy, Ming / oxidation is, is · bell alloy., indium, rare earth metals. The cathode can be produced by forming the electrode material by a method such as steaming or sputtering. Here, when the light-emitting layer is taken out from the cathode, 43 321016 200936567 is zero. * : When the light is emitted, the transmittance of the cathode is greater than 10% u, and the sheet resistance of the first pole is greater than (10) 4 The following are 隹

Wm ’且.以50至細nm為佳、： : ^ 、，形成陽極、發光層、依禽要 节主人 '及電子㈣最後形成陰略 、至陽極、與前述相反之順序__ ο 性某ί it】L 70件係在具有透*性之基板上叙作。此埤光 s tnn...:'' '.#;有機'EL:兀件之基.板:，'.:關於其透‘心 :8上），:举。棊板以平滑為隹V，Wm 'and. It is better to use 50 to fine nm, : : ^, to form the anode, the luminescent layer, the main part of the fascia, and the electron (4) to form the yin, to the anode, in the opposite order to the above __ ο ί it] L 70 pieces are described on a substrate with transparency. This twilight s tnn...:'' '.#; organic 'EL: the basis of the piece. Board:, '.: about its transparent 'heart: 8 on the line',: lift. The seesaw is smoothed to 隹V,

；：：：:^ -I :::•删 ©鋇玻蹲:、:石， :::以下之料「轉， 本f；明之有機el元件.之各層之形成方法可使用真空 .蒸鍍'電子束照射、城 或__佈m法、流錄等_成膜法之任-方法。 :此外’也可使用日本特表:2〇〇2-534782或s. T, Lee et al .Proc的dings of SID’02, ρ· 784(2002)中所記載之 UT; 乂La· Induced Thermal Imaging’ 雷知熱轉印)法、^ 321016 44 200936567 .... · · -:::刷（膠版印刷、柔性印刷、凹版㈣ 方法。：… ^ 〉 ”質遷等 .有機層以分子祿積膜特佳。在此，所謂分子堆稽 .係指由氣相狀態之材料化合物沉積而形成之薄膜、或^ . 液狀態賴相狀態之材料化合物固化而形成之膜，又泛馨' 積膜可依乾式成膜法、旋轉塗俾、浸潰、ττ =子續 九形成之薄臈（分子累積膜)，因凝輯造Ή構造之去所 〇或起咖之__—。編^藉^ ::揭示，在使樹脂等結著劑與材料化合物叙於溶劑中雨製作 :成溶液後Λ依旋轉塗_筝魏 :各層之膜厚卑##件限定，但若膜厚過厚V則為丁得到一 :ν定之本輸出' ’乘奮 ::相反地若寧厚齊琴， :0 ΐ難以得_先分的發光亮度，西此,冬層之政岸:只:i_ 1/z m為佳、以l〇nm至〇. 2// m較隹。 - ''' ..... .. ...'. :·: .: .. .. ... :本案中新謂藉由塗佈两製膜.，:係表示旋轉塗稀、浸潰、 • - ·-, · · . .. . ... . - ’...·· · · 流塗、喷墨.、噴霧法等濕式成膜法之任一者。 此外，為了提高有機EL·元件對於溫度、濕度、環境等 .... ... · - ·' · .之安定性，，也可於元择之表面設置保護層，或藉由樹脂等 將整個元件施予被覆或密封。特別是在被覆或密封整個元 .· ... ... 件時，宜使用會藉由光而硬化.之先硬化性樹脂。 對有機EL元件施加之電流通常為直流，也可使用脈衝 45 3.21016 200936567 ： 盡董以小的電能使其效率良好地發光為佳。; 有機EL το件之驅動方法不只有被動钜陣法，也可依主 動矩陣..法進行驅動。此外，從本發明之有機此元样取出光 之〒法’:不只有從陽極側取出光之所舞底部發光(“細 :emission^方蜂’也可使用從陰择側$出先之所謂復部發 ❾光（top emission)之方法。此等方法和技術係記載於城戶 淳二著，「有機EL之全鄭」:，:日本實業出版社(2〇〇3年發乂 • . . .... · . · · ： ..... - · ...·:·. · ·.·.·.，.♦. ··. .'' - ' - ·. . . . . -..：· ； * ·： ·&quot; ·· :- 」 有機EL元件之彩色也方支尤主妻克式#▲例如..:3 g 分塗方式、色轉換方式、濾色器方式。3色分塗方式可舉 例如：使用陰影遮罩（shadowrmask)之蒸鐘法 ' 和f墨法或 :印刷誇々此外，也可使用曰本特表2002-53478H S· T. £ee : et ,ai：^ Proceedings of :Sm 0之雷.射熱轉却法(Laser In如ced】er邮1 Imaging」'^ 為LITI法)，。色轉換方·式係使用發出皇光之香先；f，使先: · . ... ... .... ·， . · ... · · :通過將螢光色素分散而成之色轉換0XM)層:，轉政成波長較 • · * · · * *·. · · * -* « 藍色長之綠&amp;與紅色孓方法。濾色器方式係:使用發出白祀： :之有機五1&gt;元件，使光通適液晶用濾色器而取出3原色是光 ' . . ...... . ' .； ........ - 乏方法，除了此等3原色，也脖一部分白光直接枣出後利 . ..'-: ... ... - . , . 甩於發光，即可提高整個元件之發光效率。 .. .. . ... * ' 並且，本發明之有機EL元件也可採用微空腔：. ..(nii.crocavity)構.造。此為一種技術’係有機EL元件為在 46 321016 200936567 陽擇與陰極之間夹持有發光層之構造，所發出之光會在陽 極與陰極之間發生多重干擾，但經由邊當遽擇陽極及陰極 · - 之反射率、穿透率等光學特性、與經此等所央持之有機層 之膜厚’兩積極利用多重干擾政果，以控制自元件取出之 發光波長。藉此，也可改善發光色度。關於此多重干擾效 _ ... . ; . . V .. 果之機制，係記载於由J. Yamada等所發表之AM-LCD Digest • ... . .... ' _·;::::^ -I :::• Delete ©钡玻璃蹲:,:石, ::: The following materials "Transfer, this f; Ming's organic el components. The formation of each layer can be vacuum. Evaporation 'Electron beam irradiation, city or __ cloth m method, flow recording, etc. _ film formation method - method. In addition, you can also use the Japanese special table: 2〇〇2-534782 or s. T, Lee et al. Proc dings of SID'02, UT·784 (2002) UT; 乂La· Induced Thermal Imaging', _321016 44 200936567 .... · · -::: Brush (Offset printing, flexographic printing, gravure (4) Method.:... ^ 〉 ”Quality and so on. The organic layer is particularly excellent with molecular fused film. Here, the so-called molecular stacking refers to the deposition of material compounds in the gas phase. The film, or the film formed by solidification of the material compound in the liquid phase state, and the film of the film can be formed by a dry film forming method, a spin coating method, a dipping, and a ττ = sub-continuation of the thin film ( Molecular accumulation film), due to the condensed structure of the sputum structure or the __-. Editing ^ borrowing ::: revealing, in the resin and other materials and materials in the solvent in the rain production: into a solution After the rotation of the coating _ _ Wei: the film thickness of each layer is limited to ##, but if the film thickness is too thick V is Ding get one: ν定之本的出' '乘奋:: Conversely if the thickening of the Qinqin, :0 ΐ It is difficult to get _ the first illuminating brightness, west, the political layer of the winter layer: only: i_ 1/zm is better, l〇nm to 〇. 2// m is more 隹. - ''' .. ... .. ...'. :·: .: .. .. ... : In this case, the new method is to apply two films. The :: indicates that the spin coating is thin, impregnated, • - · - , · · . . . . . . . - '...·· · · Any of the wet film formation methods such as flow coating, inkjet, and spray. In addition, in order to improve the temperature of the organic EL component , humidity, environment, etc.. ... - - · · · . . . , can also be placed on the surface of the element of the protective layer, or the entire component can be coated or sealed by resin, etc. When covering or sealing the entire element, it is preferable to use a first hardening resin which is hardened by light. The current applied to the organic EL element is usually DC, and pulse 45 531010 200936567 can also be used. : It is better to use Dong’s small electric energy to make it shine efficiently.; Organic EL το The method is not only passive array method, but also driven by the active matrix method. In addition, the method of extracting light from the organic sample of the present invention is as follows: not only the bottom light emitted from the anode side is taken out (" Fine: The emission ^fang bee' can also use the so-called top emission method from the negative selection side. These methods and techniques are recorded in the city of Osato, "The Organic EL is all Zheng":,: Japan Industrial Press (2〇〇3 years of development • . . . . . . . .. - · ...·:········.,.♦. ··. .'' - ' - ·. . . . -..:· ; * ·: ·&quot; · :- ” The color of the organic EL element is also limited to the main wife. #▲ For example: 3 g sub-coating method, color conversion method, color filter method. For example, the three-color dispensing method can be used. The steamer method of the shadowrmask and the f-method or: printing exaggeration. In addition, you can also use the 曰本特表2002-53478H S· T. £ee : et , ai:^ Proceedings of :Sm 0. Radiation inversion method (Laser In as ced] er mail 1 Imaging" '^ for LITI method), color conversion method, the use of the scent of the emperor; f, first: · . . . . . . . , . . . . : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : : « Blue Long Green &amp; with red 孓 method. The color filter method is: using the organic 11:: organic five 1&gt; component, so that the light-passing liquid crystal filter is used to take out the three primary colors is light '. . . . . . . ..... - Lack of methods, in addition to these 3 primary colors, also a part of the white light directly after the neck. .. '-: ... - . , . Luminous efficiency. . . . . . . . * ' Also, the organic EL element of the present invention can also be fabricated using a microcavity: . . . (nii.crocavity) structure. This is a technique in which the organic EL element has a structure in which a light-emitting layer is sandwiched between the anode and the cathode at 46 321016 200936567, and the emitted light causes multiple interference between the anode and the cathode, but the anode is selected via the side. And the optical characteristics of the cathode, the reflectance, the transmittance, and the film thickness of the organic layer that is maintained by these two actively use multiple interference effects to control the wavelength of light emitted from the element. Thereby, the chromaticity of the luminescence can also be improved. Regarding this multi-interference effect _ ... . . . . V. The mechanism of the effect is described in the AM-LCD Digest published by J. Yamada et al. • ... . . .

Technical Papers，〇D-2，p:77 至 80(2〇02)。 ....' ·. . .... . .. _ Ο 如上所述，使用本發明之具有味禮基之化合物而得之 . . . · 有機EiL元并，可以低驅動電壓得到長時間之籃色發光。因 ...... - 乂， Λ ； . ' ..... - ·* ... 此，本有機EL元4可做為壁掛電視等平板顯雨器或各種乎: ·· ..... · -；.·.·.·.· - - · ... . ·· · . . · ... · ·. . . . 面發光襄也用，進一步可應用至影印機或印表機等之光 • . · . · ·· · ·.. ·· . ·..·· :源、液晶顯示器或計量儀器類等之光源v顯禾板、標示燈 ： / . .； ； ' -· . .. v. .:- .....匕-Λ. : .- .為才貪明本發明，两在i述引用各種刊物，惟將刊物 .. · , '·..* - - .- - ·_ ； .... :::中所轉乎式項:自ΐ確且鳥整地挨用誇本說明嘗中；二 办.（食施例.) :丫^ 以下:，翁由:貪施例說明本發明，但本發斑並不袁此等 實施:何任何.限定 ..· . · . · ·-:[具有咔唑基之化合物之舍:成]: (實施例1) .化合物(1)之舍▲方法 按照反應1至反應4合成化合物（1)。 47 321016 200936567 反應1Technical Papers, 〇D-2, p: 77 to 80 (2〇02). ....'.......................... _ Ο As described above, using the compound of the present invention having a taste base, the organic EiL element can be obtained with a low driving voltage for a long time. The basket color shines. Because... - 乂, Λ ; . ' ..... - ·* ... This organic EL element 4 can be used as a flat panel display such as a wall-mounted TV or a variety of: ··.. ... · -;.·.·.·.· - - · ... · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · Lights such as the watch machine. · · · · · · · · · · · · · · · : Source, liquid crystal display or measuring instruments, etc. light source, display board, indicator light: / . .; ; ' -· . . . v. .:- .....匕-Λ. : .- . For the invention of the invention, the two cited various publications, but the publications.. , , '·..* - - .- - ·_ ; .... ::: In the formula: from the confirmation of the bird and the whole land, use the exaggeration to illustrate the taste; the second to do. (Food application.) : 丫 ^ The following: , Weng: The greedy example illustrates the invention, but this spot does not limit the implementation of this: what any. Qualifications..·. · · · -: [The compound with carbazolyl: into]: ( Example 1). Compound (1) ▲ Method Compound (1) was synthesized according to Reaction 1 to Reaction 4. 47 321016 200936567 Reaction 1

(I) (II) . .···.'- 1下，.一面參照反應1 一面說明合成方法。在氮氣環 .... .&quot;. .... 境中，在-780在四氫呋喃(lOOmL)中使3-溴-9-苯基味 0 ' . 嗤(1)9. 63g(0. 03mol)、與正丁政(1. 5.2M 己烷溶液）33mL 反 :應，而將3-溴-9-苯基咔唑之3位鋰化。攪拌2小時後， ' . ...... -.... .'.圓. ... . ' ； ... 在-7 8 °C缓緩滴入棚酸三曱醋10. 3 9 g ( 0. 1 mo 1 )，並在同溫 :度進行攪拌2小時，再在室溫進行攪拌3小時。之後，在 反應生成物中加入 1%鹽酸水溶政20〇mL ϋ液禅30分鐘 .；： ；. · / V ' ' . ... . . /.；.； Λ .後，以.1%氫氧化細水溶液中和，並以醚.萃取後乾燥，藉 由蒸發器造存濃縮，而得到：8. 65g之9-苯基咔'嗤-3-硼酸 〇αΐ) ° 反應2.(I) (II) . . . . . . . . . . . . . . . . . . In the nitrogen ring ..... &quot;.., in the -780 in tetrahydrofuran (100 mL) in the 3-bromo-9-phenyl taste 0 '. 嗤 (1) 9. 63g (0. 03mol), and Zheng Dingzheng (1. 5.2M hexane solution) 33mL Reverse: should be, and the 3-position of 3-bromo-9-phenylcarbazole is lithiated. After stirring for 2 hours, ' . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9 g (0.11 mol), and stirred at the same temperature: degree for 2 hours, and then stirred at room temperature for 3 hours. After that, the reaction product was added with 1% hydrochloric acid water to dissolve 20 〇 mL ϋ liquid for 30 minutes.;: ;. · / V ' ' . . . . . . . . . . The aqueous solution of hydrogen hydroxide is neutralized, and extracted with ether, dried, and concentrated by an evaporator to obtain: 8.65 g of 9-phenylindole-3-indole-3-borate 〇αΐ) ° reaction 2.

(Ill) (IV) (V) .以下，一面參照反應.2 —面說明合成方法。在氮氣環 境中，在四 口燒瓶中加入（III)10.38g(0.04nio：l)、（IV) 48 321016 200936567 10. 〇g(0_ 05mol)、肆（三苯基膦）鈀〇· 3g、碳酸鉀(2M永溶 ' 、 . . ' · ... . ... ... 液）50g、四氫呋喃5〇g後，加熱回流5小時。之後，將反 • ' ·. · · 應液注入曱醇400mL中後:，過滤所析出之固體，並進行熱 真空乾爆，而得到粗生成物0) 1，.再將所得之粗生成物 依石夕膠管拄層:析法精製。 反應.3. : …Ά Ο(Ill) (IV) (V). Hereinafter, the synthesis method will be described with reference to the reaction. In a nitrogen atmosphere, (III) 10.38 g (0.04 nio:l), (IV) 48 321016 200936567 10. 〇g (0_ 05 mol), hydrazine (triphenylphosphine) palladium rhodium · 3 g, After 50 g of potassium carbonate (2M insoluble solution, . . . , ...), and 5 〇g of tetrahydrofuran, the mixture was heated under reflux for 5 hours. Thereafter, after injecting the liquid into the sterol 400 mL, the precipitated solid is filtered and subjected to hot vacuum dry explosion to obtain a crude product 0) 1, and the resulting crude product is obtained. According to the Shixi rubber hose layer: analytical purification. Reaction.3. : ...Ά Ο

Br2 CCI4Br2 CCI4

(VI) -* _ . - , · - ·. . . 以下面參照友應3 一南說明合成方法β在氮氣環 · · ..二..；'·-- .. ·： 境中，:在三口燒瓶申加入(V)l 〇g(Q, 〇33mol h /ISOmL笨’使用滴液漏斗諼缓滴入漬5. 8它作.033111〇1)、四 -- 分.:滴入結東後，i r溫迤行姝拌1:小時後，:以磕代^麄: 納水溶液:結束反4。之後，將有機層中和，，並進行水洗後， · .. - · . · . ... . · ... 以蒸發器去每溶劑。將為得之黃色粉末以曱本進行再結 321016 49 200936567 • 反應4(VI) -* _ . - , · - ·. . . The following is a description of the synthesis method β in the nitrogen ring · · .. two..;'·-- .. ·: in the context of: In the three-necked flask, add (V) l 〇g (Q, 〇33mol h /ISOmL stupid 'use the dropping funnel to gently drip into the stain 5. 8 it is made. 033111 〇 1), four --- points.: drip into the knot After the east, ir 迤 迤 姝 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 After that, the organic layer is neutralized, and after washing with water, ·.. - · · · · · · · · · Evaporator to remove each solvent. The yellow powder obtained will be re-knotted with transcripts 321016 49 200936567 • Reaction 4

以Τ，一面參照反應4—面說明合成方法。在氮氣環 ©The synthesis method will be described with reference to the reaction 4-face. In the nitrogen ring ©

境中&gt; 在四口燒蜂中和人(γι)4· 09g(0· 01mol) ^ . · · - · (0.:012mol)、辞(三苯基膦）免〇. 3g、:碳酸鉀（2M水溶液）: ....... -..... ..... - . ... · . - 5〇g、四JL呋嘀5〇g後’加熱回流:5小時。之後；，.將反應液 v注入甲醉4〇〇此:中後，遍滅所希出之固體，並進行熱真空v: :々聲燥’ ffe得到粗矣成物(化合物(1))3 」_成物依砍膠實柱厚析绛糈製:、，，苒离疗昇華:精製.〇籍由質譜 (Bruker DaJtoMcs 公司製::，Autof 1 ex C13-NMR(日本電夺製:，财-4〇〇?)鑑定化合物(1)。化合物阳 Ήν光譜、煢考(PJL)光譜分別知第1阖及第2圖所示。再 者？ uv光譜傣藉由日立分光（股)製光度計（υ_35〇〇)進行韌 .定’:螢光(PL)光譜係:藉由曰:立分光(股：)製螢光分光光度許 (FP-6500)進行測定。:：：：心」 :再者，合成化♦物(1)時所使用之卜溴_9_苯基咔唑⑴ 係使用按照W02007/43484中所記载之方法而合成者。4__ 321016 50 200936567 .聯苯硼酸（II)、9-溴蒽（in)係使用市售之試劑。 根據第1圖之從光譜，峰頂為378皿、.398皿 • . _ 之’得知為可見类區域不具有吸收之化合物。根據第2圖 1螢光光譜，峰頂為436. 5nm。換言之，得知為在藍色發 ... ... .· 光區域（470nm以下）有.榮光。由於螢光光譜與EL光譜（發 :光光譜)大約一致，故接測製作成EL·元件後之發光:色為藍 ......色.二 ... - .. · · ..... ..... (實施例2至50) 0' ；.&quot;： ' 合成方法係從上述之反應式友下‘所示之反應5至反 應11:申組合，而合成表X中之化舍物(2)至(5:0)。湖於各 .... . . ... . # · · .·；：·'. . _ . ' · .- 丨反應式之組合;，如表7所示。： :..V.反應’5. ΟIn the environment&gt; in the four-burning bee neutralized human (γι) 4· 09g (0· 01mol) ^ . · · - · (0.:012mol), the words (triphenylphosphine) free. 3g,: carbonic acid Potassium (2M aqueous solution): ....... -..... ..... - . . . - - 5〇g, four JL furan 5嘀g, 'heated reflux: 5 hours . After that;, the reaction solution v is injected into the drunken 4 〇〇 this: after the middle, the solids are annihilated and subjected to a hot vacuum v: : 々 燥 dry ' ffe to obtain a crude mash (compound (1)) 3 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ , Finance-4〇〇?) Identification of compound (1). Compound Yangshuo ν spectrum, PKL spectrum (PJL) spectrum is shown in Figure 1 and Figure 2. Again? uv spectrum 傣 by Hitachi spectrometry The photometer (υ_35〇〇) is toughened. ': Fluorescent (PL) spectroscopy system: It is measured by 曰: 立分光(股:), the spectrophotometric luminescence (FP-6500).:::: Further, the bromine- 9-phenylcarbazole (1) used in the synthesis of the object (1) is synthesized by the method described in WO2007/43484. 4__ 321016 50 200936567 . Boric acid (II) and 9-bromoindole (in) are commercially available reagents. According to the spectrum of Figure 1, the peak top is 378 dishes, .398 dishes•. _ 'is known as visible areas without absorption Compound. According to Figure 2, the fluorescent light The peak is 436. 5 nm. In other words, it is known that it is in the blue light... The light region (below 470 nm) has glory. Since the fluorescence spectrum is approximately the same as the EL spectrum (hair: light spectrum) Therefore, the light after the EL component is measured: the color is blue... color. two... - .. · · ..... ..... (Examples 2 to 50) 0';.&quot;: 'Synthesis method is from the reaction 5 shown in the above reaction formula to the reaction 11: combination, and the compounds (2) to (5:0) in Table X are synthesized. Lake in each .... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . '5. Ο

G ·ΟΜ_G ·ΟΜ_

R1 Μ (VJ I) ' 广 (VXI I) R1(1至R16、及R22至R2?分別獨立地表示氫原夺、函素原 » - . . ' . .. . . . . ； . ·'' 子、.1價有:機残基。合成方法係依一般方法，:在氮氣氣流 下，在-78π，使正丁娌(n-JBuLi)與3-溴-9-苯基咔唑祷生 ... · . . · ·. ... . · · .· 物(V11)反應而進行鋰化後，使B ( OMe)3與所生成之丄i衍生 物反應，而合成目標之删酸衍生物（VI11)(參照反應5 )。 51 321016 200936567 反應6R1 Μ (VJ I) '广XI (VXI I) R1 (1 to R16, and R22 to R2? independently represent hydrogenogen, elementogen» - . . . . . . . . . . 'Sub, .1 price has: machine residue. The synthesis method is based on the general method: under the nitrogen gas flow, at -78π, the n-JBuLi and 3-bromo-9-phenylindole Raw... · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · · Acid derivative (VI11) (refer to Reaction 5). 51 321016 200936567 Reaction 6

(IX) . (V】1 i) ... ... . ..… . -·；'(χ) R1至:R9分別獨立地表示氫原羊、;滷素原子、:1價有機 殘基。合成歹法係’除了使用9_漢篇衍生物(IX)〇·: Olmol 來代(VI)，;及使用咔唑衍生物(VIIΓ) 0. 012mo 1取代（11)， • . · - 並使兩者反應.以外，其餘與實施例1之反應4進行同樣操 '·: · . ：/ ； ' .... ... -.. 作，'而得到目標化合物〇〇(參照反應β)。&quot; ： ：; 反應7 厂(IX) . (V)1 i) ... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Synthetic oxime method 'except for the use of 9_Han derivative (IX) 〇: Olmol (VI); and oxime derivative (VIIΓ) 0. 012mo 1 substituted (11), • . Except for the reaction of the two, the rest of the reaction with the reaction of Example 1 was carried out '.: . : : ; ' . . . . . . . . . . . ). &quot; : :; Reaction 7 Factory

(X) (XI) . ... ........... ... · . · · 除了將（V)變更為（X)0. 033mol以外，其餘與實施例1 52 321016 200936567 :之反應3同樣將00漠化，而得到（XI)(參照反應7)。 反應8(X) (XI) . ....................... In addition to (V) changed to (X) 0. 033mol, the rest and the embodiment 1 52 321016 200936567: Reaction 3 also desertified 00 to obtain (XI) (refer to Reaction 7). Reaction 8

(XIII) (xv&gt; .. ·- . ......... -· · - -. - · E1至R9及飞17至R21分別獨立地表示氫原子、氣素原子、 黟1價有機殘合成方基係，除了使用9_漠蒽衍生物:(xm): :0. 04m0l取杈（ΙΠ)，及使用苯衍生物(11乃〇. 〇5111〇1取代: :Civ)，並使海養反;t以夕F，其嫌與實綠例1乏反應2進行: • ： . · · ·....· .... -· - - - - · ·.： · · - . .. .... ·. 同檬搡作…而得到目標化合物（XV)(參照反應8)。.:(XIII) (xv&gt; .. ·- . . . -· · - - - - E1 to R9 and 17 to R21 independently represent a hydrogen atom, a gas atom, and a valence The organic residue is synthesized in addition to the 9_ desert derivative: (xm): :0. 04m0l is taken from 杈 (ΙΠ), and the benzene derivative (11 is 〇. 〇5111〇1 is substituted: :Civ), And make the sea raise the opposite; t is the evening F, and it is suspected to react with the real green case 1 2: • : · · ·....· .... -· - - - - · ·.: · · - . . . .... ·. With the lemon ...... and the target compound (XV) is obtained (refer to Reaction 8).:

合成方法祿/除了使用蒽街生狄(XIX)O. OWmol取代 . · &quot; ' . ' · (V)以外，其餘與實施例1之反應3同樣進行溴化，而得到 . -· · · · - . ...·.- · . . .·——.· ·. (XX)(參照反應9)。溴化可彳吏用溴或_NBS(N-缜玻拍醯亞 - · · 胺）’並依一般方法進行。 53 321016 200936567 反應ίοThe synthesis method is in addition to the use of 蒽 生 生 (XIX) O. OWmol replaced. · &quot; ' . ' (V), the same as the reaction of Example 3 bromination, to obtain. -· · · · - . . . . . . . . . . . . . . . . . . . . Bromination can be carried out by a conventional method using bromine or _NBS (N-indole). 53 321016 200936567 Reaction ίο

- .(XXII)；,；· 合成方法係，除了使用9-漠:蒽衍生物（XX)0. Olmol取 代(Vl·):，及使用叶ΐ衍生物(ΗΠ )0· 01知〇1本我(.11 y厂 - ·. . . - . . . · ... ·. ..... :像兩考反應以外，秦餘與貪施例1名反應4準行同樣操作， ^得到目標化合物αχιι)(參照犮應ίο)。 . .- ：. ... -· ' . ·-- (XXII);,;· Synthetic method, except for the use of 9-molyst: anthracene derivative (XX) 0. Olmol substitution (Vl·):, and the use of spider mites derivatives (ΗΠ) 0· 01 knowledge 1 Ben (.11 y factory - ·. . . - . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . The target compound αχιι) is obtained (refer to 犮应ίο). . .- :. ... -· ' . ·-

(χι) (χιν) (XXI I) 合成方法係，徐了使用(XI)〇. 〇4mol:取代（111)，及使 用（XIV)O. 〇5mol取代（IV)以外，其餘與實施例1之反應2 • · - 54 321016 200936567 進行同樣操作，藉此得到目標化合物（χχπ)(參照反應11)。 [表 7]-. 實施例 .化合物 所使用之反應” 取代位置u . 取代基之種類*3 1 (1) 1, 2, 3, 4 R18 苯基 2 (2). 5, 2, 3, 10 :R1B .R24 苯基、_ 曱基. 3 (3) 5, 2, 3, 10 · . - R19,. ： R2i : 苯基、 三級丁基 4: (4) 5，2，3，10 :R19 ’ R24 '苯基 5, (5) ：5, 2, 3, 10 ； R19 r25、r26 苯基、 形成苯.環 6' (6) &lt; - ... ·. 5，: 2，3，10 R19 :R25、R26 苯基' :形咸苯環 .7. (7). 1, 8,； 9, 10 .R2 三級丁基：. 8 (8) 1, 8, 9, 10 R2 苯基 9 (9) 5., 8，9，10 R17、R19、 厂R21、R2&lt; - ::.曱基、: 苯基：' 、10 (10) V •‘ · · ·.. 5, 8, a, 10 • . · · · : . R19' '三奴丁基:、… .甲基 Π V :(11)::: 1，8/ 9, 10 :d 〃形成苯環） \ 1:2 (12&gt; •· ' - '· ·. · .' .... - · . • · ·. ... : · - ::R2 .、.:: :Rie、:R1B、： ::R24 ./ 苯基、: 形成笨環、 、..m _v • · . ··' 13 (13) ;h 8, 9, 10 RZ-R7-： J R18 、 R19 「苯基、丨 形成苯環 14 (14). • · . ·. · 1, 8, 9, ίο： - ·. - ' E2' E8 V :R18、Eie : 苯基、 .形成苯環. 1.5:.. (15). 1:, 8，9，10 R2、R7、 R18 ' R1B 甲基、. 形成苯環 16 (16) 5，:8，V 10、 R18.、R19、 R24、R25 形成苯環、 #成苯環 17 (17) 5，8.，9，10 Ei8 &gt; R19' R22、R23 形成東環、 形成苯環 18 08) 1，8，9，10 R17、R18、 R2。、R21 形成苯環、 形成苯環' 55 321016 200936567 Ο 〇 19: (19) 1, 8, 9, 10 .i?17、R18、 R2。、R21、 R19 形成苯環、 形成苯環、 苯基 20 (20) ；1； 8, 9, 10 R17、R18 形成苯環 .21 (21) 1, 8, 9, 10 Ε1Β . Λ 聯苯基 22 (22) 5, 8, . 9, 1〇 RI8、lT、 R22、R23 形成含有苯基 之苯環、 形成苯環 23 (23) 5, 8, 9，1〇 ·, · ：：R19 ' R22、R23、 :R25、R2S : 二苯基胺基、 形成苯環、:: 形成苯環 ：.24 (24) 1, 8, 9, 10 R19 苯并噻吩基 25 (25) 1, 8, 9, 10； ,R19 ： 苯并呋喃基 .26 (26) 5, 6，7，Ιί , R3、 R18、R19、 R24 苯氧基V 形成笨環、 :甲氧基 27 ： '(27) -- :. - .5，V 7，: 11 .... r、:r8、： R17、R18、' 噻吩基、': ..形成苯環、. ..氟. ·, . -28 ·.·.··.. .... . · (28)： .... ·· '· · .. . ... . · 5，6, 7.，11. ...I* · . · ... • ... . ' ··- --' R?、R8、: R17 ' .. . R24 乙基:、：. 形成苯環、 :硫甲基、 .甲羰基、^ : ；29 .. .... ..'.· .(29) 5y 6，:7，:11 :: 'Ύ、.' ' V . R24' :: :苯基緩基、. .甲基羧基:1 30，. ：(30)； 1, 8, 9, 10 • · .·. E2、R7、: :入 Rie ' V .二乙基胺基 ::苯磺祕基./ 31 ,.(31；)： 1, 8, 9, 10 .R18 ' R18 ' 三級丁基、 形成苯環 32 (32) 1，8，9，10 :—R?8、Rie、 R2。、R21 . 形成苯環、 形成苯環. 33 (33) 1, 8， 9， 10 :V R2、 R18、R19、 R2。、R21:: 三級丁基、 形成苯環、 '形成苯環 34 (34) 1，8，9，10 ’ i2、. R18、R19、 R2°、R2丨 ..苯基' : 形成苯環、 形成苯瓖 35 (35) 1，8，9, 10 R2、 R18、R18、 R19、R2。 三級丁基、 形成苯環、·. 形成苯環 1 56 321016 200936567 (36) 1, 8，9，10 R18、R18、 R19、R2。 形成苯環、 形成苯環 37 (37) 1，8，9，10 R19、R2。、 R20 ' R21 形成苯環、 形成苯環 (38) 1, 8, 9, 10(χι) (χιν) (XXI I) Synthetic method, using (XI) 〇. 〇 4mol: substituted (111), and using (XIV) O. 〇 5mol instead of (IV), the rest and Example 1 Reaction 2 • · - 54 321016 200936567 The same operation was carried out, whereby the target compound (χχπ) was obtained (refer to Reaction 11). [Table 7]-. Example. Reaction used for the compound" Substitution position u. Type of substituent *3 1 (1) 1, 2, 3, 4 R18 Phenyl 2 (2). 5, 2, 3, 10 : R1B .R24 phenyl, _ fluorenyl. 3 (3) 5, 2, 3, 10 · . - R19,. : R2i : phenyl, tert-butyl 4: (4) 5,2,3, 10: R19 ' R24 'phenyl 5, (5) : 5, 2, 3, 10 ; R19 r25, r26 phenyl, benzene. Ring 6' (6) &lt; - ... ·. 5,: 2 , 3,10 R19 : R25, R26 phenyl ' : salty benzene ring. 7. (7). 1, 8,; 9, 10 .R2 tert-butyl: 8 (8) 1, 8, 9, 10 R2 Phenyl 9 (9) 5., 8,9,10 R17, R19, Plant R21, R2 &lt; - ::. Mercapto, Phenyl: ', 10 (10) V • ' · · ·.. 5, 8, a, 10 • . · · · : . R19' '三奴butyl:,... .methylΠ V :(11)::: 1,8/ 9, 10 :d 〃 forms a benzene ring) \ 1:2 (12&gt; •· ' - '· ·. · .' .... - · . • · ·. ... : · - ::R2 .,.:: :Rie, :R1B, : ::R24 ./Phenyl, : Forming a stupid ring, , ..m _v • · · ··· 13 (13) ;h 8, 9, 10 RZ-R7-: J R18 , R19 "Phenyl, hydrazine formation Benzene ring 14 (14). • · . ·. · 1, 8, 9, ο: - ·. - ' E2' E8 V : R18, Eie : phenyl, . Forms a benzene ring. 1.5:.. (15). 1:, 8,9,10 R2, R7, R18 ' R1B methyl, Forming benzene ring 16 (16) 5,:8, V 10, R18., R19, R24, R25 forming a benzene ring, #成苯环17 (17) 5,8.,9,10 Ei8 &gt; R19' R22 R23 forms the east ring, forms the benzene ring 18 08) 1,8,9,10 R17, R18, R2., R21 forms a benzene ring, forming a benzene ring' 55 321016 200936567 Ο 〇19: (19) 1, 8, 9 , 10 .i?17, R18, R2. , R21, R19 form a benzene ring, form a benzene ring, phenyl 20 (20); 1; 8, 9, 10 R17, R18 form a benzene ring. 21 (21) 1, 8, 9, 10 Ε 1 Β . 联 biphenyl 22 (22) 5, 8, . 9, 1 〇 RI8, lT, R22, R23 form a phenyl ring containing a phenyl group, forming a benzene ring 23 (23) 5, 8, 9, 1 〇 ·, · ::R19 ' R22, R23, :R25, R2S : Diphenylamino group, benzene ring formation, :: Formation of benzene ring: .24 (24) 1,8, 10 10 R19 benzothienyl 25 (25) 1, 8, 9, 10; , R19 : benzofuranyl. 26 (26) 5, 6,7, Ιί , R3, R18, R19, R24 phenoxy V form a stupid ring: methoxy 27: '(27) - - :. - .5,V 7,: 11 .... r, :r8,: R17, R18, 'thienyl, ': .. form a benzene ring, . . . fluorine. ·, . -28 ·. ····.. .... . · (28): .... ·· '· · .. . . . · 5,6, 7.,11. ...I* · . ... • ... . ' ··- --' R?, R8,: R17 ' .. . R24 Ethyl:,:. Forms a benzene ring, : thiomethyl, .methylcarbonyl, ^ : ;29 .. .. ..'.· .(29) 5y 6,:7,:11 :: 'Ύ,.' ' V . R24' :: :Phenyl slow-base, . .methylcarboxy:1 30,. :(30); 1, 8, 9, 10 • · .·. E2, R7, : : into Rie ' V . Diethylamino :: benzenesulfonyl. / 31 ,. (31;): 1, 8, 9, 10 .R18 ' R18 'tertiary butyl, forming benzene ring 32 (32) 1,8,9,10 :-R?8, Rie, R2. , R21 . Form a benzene ring to form a benzene ring. 33 (33) 1, 8, 9, 10 : V R2, R18, R19, R2. , R21:: tertiary butyl, forming a benzene ring, 'forming a benzene ring 34 (34) 1,8,9,10 ' i2, R18, R19, R2°, R2丨..phenyl' : forming a benzene ring Forming phenylhydrazine 35 (35) 1,8,9, 10 R2, R18, R18, R19, R2. Tertiary butyl, forming benzene ring, forming benzene ring 1 56 321016 200936567 (36) 1, 8,9,10 R18, R18, R19, R2. A benzene ring is formed to form a benzene ring 37 (37) 1,8,9,10 R19, R2. , R20 ' R21 forms a benzene ring and forms a benzene ring (38) 1, 8, 9, 10

Rz v Rie ' R2。、 R20 ' R21 三級丁基、 形成苯環、 形成苯環 39 (39) 1, 8, 9, 10. R2、 Rie、R2。、 R2。、.R21 三級丁基、 形成環、 形成苯環 40 (40) 1, 8, 9, 10 R18、R2。、 :R2°、R21 形成環、 形成苯環 〇 41 (41) 1, 8, 9, 10Rz v Rie ' R2. , R20 ' R21 Tert-butyl, forming a benzene ring, forming a benzene ring 39 (39) 1, 8, 9, 10. R2, Rie, R2. , R2. , R21 tertiary butyl, forming a ring, forming a benzene ring 40 (40) 1, 8, 9, 10 R18, R2. , :R2°, R21 form a ring, forming a benzene ring 〇 41 (41) 1, 8, 9, 10

R2 R19、R 20 三级丁基 形成環 42 (42) 1, 8, 9, 10R2 R19, R 20 tertiary butyl forming ring 42 (42) 1, 8, 9, 10

Rie、R 20 形成環 43 (43) 1. 8, . 9, 10 R2、 R19、R2。、 R20 &gt; R2· 三級丁基、 形成環、 形成苯環 44 (44) 1, 8, 9, 10： R19、R2。、 R20' R21 形成環、 形成苯環 45 (45): :: 1，8, .9，10 E2、. R18、R18, Rlfl、R2。， :浐。、R21 三級丁基、 形咸苯琅、 形成苯瓖、 形成苯環Rie, R 20 form a ring 43 (43) 1. 8, . 9, 10 R2, R19, R2. , R20 &gt; R2 · Tert-butyl, forming a ring, forming a benzene ring 44 (44) 1, 8, 9, 10: R19, R2. R20' R21 forms a ring and forms a benzene ring 45 (45): :: 1,8, .9,10 E2, R18, R18, Rlfl, R2. , :浐. , R21 tertiary butyl, salty benzoquinone, benzoquinone, benzene ring

G 46 ： (m 8, 9, 10 R1 &gt; R19 ' R18 ' R20 &gt; .R2。、R21 形威苯環、 形成苯 形成苯環 47 (47) 8, 9, 10 R2、: R.1S、R2。 三級丁基、 形成苯環 48 (48) 1, 8, 9, 10G 46 : (m 8, 9, 10 R1 &gt; R19 ' R18 ' R20 &gt; .R2., R21 Form benzene ring, form benzene to form benzene ring 47 (47) 8, 9, 10 R2:: R.1S , R2. Tert-butyl, forming benzene ring 48 (48) 1, 8, 9, 10

Rie、R2。 形成苯環 49 (49) . 1，8，9，10 R7:、： RI7、.R18、 R19、R2。 三級丁基、 形成笨環、 形成苯環 50 (50) 1, 8, .9； 10 R2 、 R7 、 R17、.E18、 R19、R20 苯基、 .形成苯環、 形成苯環 57 321016 200936567 ♦ - . -對於將以上之反應 1至反應11組舍而得之本發明之化 σ物之才冓造’以質譜（Bruker Daitonics公司製，Autoflex JI)鑑定。結果如表8所示。再者，化合物編號與表1相同。 此外’做為具作表性之化合物之化合物（11)、(20)、（32) .. .. . · . . . .. . .. 之UV光谱、螢光（PL)光譜分別如第3 .圖至第8圖所示。 ❹ :根據第3圖之uv光譜，峰頂為378冊、:3&amp;8nm。換言 之’传知化合物(11)在可見光區域不具有吸收。根據第4 辱之榮光*譜’峰頂為435nm。換言之，在藍色發光區域 .....: * 。由於螯光光譜與EL光譜(發光光譜) 大約”致’故推測使用作合物(11)製作成EL元件後之發光 色 +為:藍表: 濟據第5圍之IJV光譜，峰頂為377而、卿.5nm。換 p之:·知也合物伽〉在苛見先區域不真有吸收。叔據第 .Μ7— *下)有魏’_ 办啤之發光έ為藍色 ,Η - ^ 378nm &gt; 398/5n ί知化合物(32)在可見光區球不具有吸收。根據第: δ ® ^ f ^Λ：：43〇. 5ηΐη ；〇； ^ M ^^ 下姆光，韻使㈣ :件後之發光色為藍色。 :: V? - · . · · . . ·-·...· 321016 58 200936567 ][表 8] Ο 〇 實施例 化合物 質譜實測值 理論值 1 :.⑴ 571. 83 571.. 70 2 ⑵ 575. 39 575. 73 3 (3) 527.52 . 527, 81 '4 .(4) 647. 49 647. 80 5 (5) - 621.50 621.76 6 (6) 621.60 621. 76 7·： :⑺丨 \ 551.38 551.72 : 8 (8) 571.45 - .- .. . 571.71 ' 9 Λ⑻: 613.55 613. 79： 人 10 :: (10) 565.38 .'565. 74： . 11:: (11) .545.61 1 :545. 67 1.2 ::(12): .646. 46 646. 78 - - &quot; -.V .:13 、(13) • .... · 698,02 ,697. 86 .V:: 1:4.: V .::: ? :(1:4) 698. 12 697.86 . ....··' . ·· - · | ' ' .1:5'. 乂 .(15):: 573；98 57:3: 72 16 * ’ - - * * - * ' (16): ；595. 50 ；： ' 595. 73 ' | ；：17 ；/ ；(17)/ :: 595. 45:::. ： 595. 73 V. 18 ^ 595/56 595. 73 :19 (19)： 671.67 671, 83 Ί 20 (20) 545. 88- 545.67 .·· 21 Λ (21) ； 647.92 &gt; 647. 80 22 (22)广 - 645..57 / 645.79； ： 23 (23). ；763. 04 762. 94 .; 24 (24) 628. 08 627.79 I， .25 (25) 688.14 687. 82 59 321016 200936567 26 (26) • 745. 65 745. 88 27 (27) 779. 71 ； 779. 98 .28 (28) 786.8.2 787. 06 29 (29) 673. 54 673.75 30 (30); 778.35 . 778.01 31 . (31) 601.56 601. 78 32 (32)： 595.63 595. 73 , 33 (33) 651.56 651. 84 :34 (34)： 671. 96 671. 83 .35 .(35) 675. 63 675. 86 36 ;(36) 619.52 . 619.75 : 37 .(37)： 619. .91.:: :619. 75. ' ：38 (38). ,675.66 ；675. 86 ； 39 ： (39)：/ ： .'675.95 / 675.. 86 · 40 , (40)； 619.45 ；' 619. 75 .41:: (41) 701.42.' 701. 89 、.(42)' : ； 645. 95; 645.79 .； 43 ::、 \ (43) ' 725.57 ； ^ 725； 92 ： .44 . ·： · .. 669.65 ' :6 6 9:. 81 45 '； ' ；；(45) V . 675. 59 : 675. 86 46 V , (46); 619.98 619. 75 47 ； ' (47) . 651.78 651.84 48 (48) 595.59 595- 73 49 . ：(49) 651: 63 ；651.84 50 - · - -- (50) 747. 80 .747.92Rie, R2. Formation of benzene ring 49 (49) . 1,8,9,10 R7:,: RI7, .R18, R19, R2. Tertiary butyl, forming a stupid ring, forming a benzene ring 50 (50) 1, 8, .9; 10 R2, R7, R17, .E18, R19, R20 phenyl, forming a benzene ring, forming a benzene ring 57 321016 200936567 ♦ - - - The sigma of the present invention obtained by the above reaction 1 to the reaction 11 was identified by mass spectrometry (Autoflex JI, manufactured by Bruker Daitonics Co., Ltd.). The results are shown in Table 8. Further, the compound numbers are the same as in Table 1. In addition, the UV spectrum and the fluorescence (PL) spectrum of the compounds (11), (20), (32), . . . . . . . . . . . . . . 3. Figure to Figure 8. ❹ : According to the uv spectrum of Fig. 3, the peak top is 378 volumes, 3: 8 nm. In other words, the compound (11) is known to have no absorption in the visible light region. According to the 4th glory of the glory* spectrum, the peak is 435nm. In other words, in the blue light-emitting area .....: *. Since the chelation spectrum and the EL spectrum (luminescence spectrum) are approximately "caused", it is presumed that the luminescent color after the EL element is produced using the composition (11) is: blue table: the IJV spectrum of the fifth circumference, the peak is 377, qing. 5nm. For p: · know the compound gamma > does not really absorb in the harsh first area. Uncle according to the first. Μ 7 - * below) there is Wei '_ the light of the beer is blue, Η - ^ 378nm &gt; 398/5n 知 know that compound (32) does not absorb in the visible light sphere. According to the first: δ ® ^ f ^Λ::43〇. 5ηΐη;〇; ^ M ^^ 下姆光,韵使(四) : The illuminating color after the part is blue. :: V? - · · · · · · ····· 321016 58 200936567 ][Table 8] Ο 〇 Example compound mass spectrometry measured value 1 :. (1) 571. 83 571.. 70 2 (2) 575. 39 575. 73 3 (3) 527.52 . 527, 81 '4 .(4) 647. 49 647. 80 5 (5) - 621.50 621.76 6 (6) 621.60 621. 76 7·: :(7)丨\ 551.38 551.72 : 8 (8) 571.45 - .- .. . 571.71 ' 9 Λ(8): 613.55 613. 79: Person 10 :: (10) 565.38 .'565. 74: . 11:: (11) .545.61 1 :545. 67 1.2 ::(12): .646. 46 646. 78 - - &quot; -.V .:13 , (13) • .. .. · 698,02 ,697. 86 .V:: 1:4.: V .::: ? :(1:4) 698. 12 697.86 . ....··' . ·· - · | ' ' .1:5'. 乂.(15):: 573;98 57:3: 72 16 * ' - - * * - * ' (16): ;595. 50 ;: ' 595. 73 ' | ;: 17 ;/ ;(17)/ :: 595. 45:::. : 595. 73 V. 18 ^ 595/56 595. 73 :19 (19): 671.67 671, 83 Ί 20 (20) 545. 88- 545.67 ..· 21 Λ (21) ; 647.92 &gt; 647. 80 22 (22) wide - 645..57 / 645.79; : 23 (23). ;763. 04 762. 94 .; 24 (24) 628. 08 627.79 I, .25 (25) 688.14 687. 82 59 321016 200936567 26 (26) • 745. 65 745. 88 27 (27) 779. 71 ; 779. 98 .28 (28) 786.8.2 787. 06 29 (29) 673. 54 673.75 30 (30); 778.35 . 778.01 31 . (31) 601.56 601. 78 32 (32): 595.63 595. 73 , 33 (33) 651.56 651. 84 :34 (34): 671. 96 671. 83 .35 .(35) 675. 63 675. 86 36 ;(36) 619.52 . 619.75 : 37 .(37): 619. .91.:: :619. 75. ' :38 (38). , 675.66; 675. 86 ; 39 : (39): / : .'675.95 / 675.. 86 · 40 , (40); 619.45 ; ' 619. 75 .41:: (41) 701.42.' 701. 89 .(4 2)' : ; 645. 95; 645.79 .; 43 ::, \ (43) ' 725.57 ; ^ 725; 92 : .44 . ·: · .. 669.65 ' :6 6 9:. 81 45 '; (45) V . 675. 59 : 675. 86 46 V , (46); 619.98 619. 75 47 ; ' (47) . 651.78 651.84 48 (48) 595.59 595- 73 49 . :(49) 651: 63 ;651.84 50 - · - -- (50) 747. 80 .747.92

[有機EL元件之製作]. 以下，藉由下述實施例說明將本發明之化合物做為有 60 321016 200936567 * 機EL元件用#料使用而得之有機EL元件之製作例，但本 發明並不受下述之實施例所限定°在實施例中，只要未特 別說明，混合比即表示所有重量比。蒸鍍（真空蒸鍍）係在 10_6Torr之真空中’在不進行基板加熱、.冷卻等溫度控制 之條件下進行。此外’在評估元件之發光特性時，係測定 發光面積2ππηχ2ιηπι之有機EL元件之特性。 (實施例51) 在經洗淨之附有1T0電極之玻璃板上，將表3之HTM8 ❾真空蒸鍍而得到膜厚6〇nm之電洞注入層。接著.，:將本發明. 之表1中之化合物（1)真空蒸鍍而得到膜厚50nm之發光 層。並且，將參（8_羥基啥啉）鋁錯合物（Alq3)真空蒸鍍而 製作成膜厚2 〇加I之電子注入層]並在其上首先蒸鍍氟化鋰 1ι?·ΐη，接著蒸艘铭（Al)200nm而形成電極，而得到有機肛 .... v · ·-. ·. . · · 元件。此元件係在顯示發光亮度11000(cd/m2)之藍色發 其色度孫1=0.16，尸0‘ 05。測定以發光亮度500(cd/ni2) 〇.在室温將此元件進行定電流驅動後之亮度半表壽命。此. 外，測定以電流密度10mA/cm2驅動後之初期亮度、及在 80 c之環境連續驅動100小時後之亮度。結.果如表9所示.。 (實施例52多80) 除了使用表1所示之化合物（2)至化合物(46)取代化 今物（1)製作成發光層以外’其餘與實施例51同樣製作成 =件。測定以發光亮度500(cd/m2)在室溫將此等元件進行 二電，驅動後之亮度半衰壽命。此外，測定以電流密度i〇mA •咖驅動後之初期亮度、及在8(rc之環境連續驅動⑽ 321016 61 200936567 .小時後之亮度。結果如表9所示。 (比較例1) 除了使用下述所示之化合物（A)製作成發光層以外，其 餘與實施例51同樣.製作成元件。此元件係顯示藍色發光。 測定以發光亮度5 〇0 (cd/m2)在室溫將此元件進行定電流驅 動後之焭度半哀哥命。此外，測定以電流密度1 〇mA/ cm2 驅動後之初期贵度、及在80°c之環境連續驅動loo小時後 之免度。結果如表9所示。[Production of Organic EL Element] Hereinafter, an example of the production of the organic EL element obtained by using the compound of the present invention as a material for the EL element of 60 321016 200936567* will be described by way of the following examples. It is not limited to the following examples. In the examples, the mixing ratio means all the weight ratios unless otherwise specified. The vapor deposition (vacuum evaporation) was carried out in a vacuum of 10-6 Torr under the conditions of no temperature control such as substrate heating or cooling. Further, in evaluating the light-emitting characteristics of the element, the characteristics of the organic EL element having the light-emitting area of 2ππηχ2ιηπι were measured. (Example 51) On a glass plate with a 1T0 electrode attached thereto, HTM8 of Table 3 was vacuum-deposited to obtain a hole injection layer having a film thickness of 6 Å. Next, the compound (1) in Table 1 of the present invention was vacuum-deposited to obtain a light-emitting layer having a film thickness of 50 nm. Further, the ginseng (8-hydroxyporphyrin) aluminum complex (Alq3) was vacuum-deposited to prepare an electron injecting layer having a thickness of 2 Å and I was deposited thereon, and first, lithium fluoride 1 ?··ΐ was deposited thereon. Then steamed the Ming (Al) 200nm to form an electrode, and obtained an organic anus.. v · ·-. ·. · · · Components. This component is in the blue color of the display luminance of 11000 (cd/m2). Its color is 1+1.16, and the body is 0'05. The luminance half life of the device was measured by a constant current driving at room temperature of 500 (cd/ni2) 室温. In addition, the initial luminance after driving at a current density of 10 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 80 c were measured. The results are shown in Table 9. (Example 52: 80) A compound was produced in the same manner as in Example 51 except that the compound (2) to the compound (46) shown in Table 1 were used instead of the luminescent layer (1). These elements were subjected to two-electrode emission at a luminance of 500 (cd/m2) at room temperature, and the luminance half-life after driving was measured. In addition, the initial brightness after the current density i 〇 mA • coffee was driven, and the brightness after continuous driving (10) 321016 61 200936567. hours in 8 (rc environment). The results are shown in Table 9. (Comparative Example 1) Except for use The compound (A) shown below was produced in the same manner as in Example 51 except that the compound (A) was prepared in the same manner as in Example 51. This device showed blue light emission. The measurement was carried out at a luminance of 5 〇0 (cd/m2) at room temperature. The temperature of the component is driven by constant current driving. In addition, the initial gratification after driving at a current density of 1 〇 mA/cm 2 and the degree of exemption after continuously driving loo hours in an environment of 80 ° C are measured. As shown in Table 9.

(比較例2至3) • . · · 除了使用下述所示夂化合物(Β)及（C)製作成發光層以 .外，其餘與實施销51同樣製作成元件。測定以發光亮度 ❹5 0 0 (cd/m2)在室溫將此等元件進行定.電流驅動後之亮度半 衰壽命6此外，測定以電流密度lOmA/cm2驅動後之初期亮 .度、及在80°C之環境連續驅動10 0小時後之亮度《«結杲如 表9所示。(Comparative Examples 2 to 3) The components were produced in the same manner as the pin 51 except that the ruthenium compound (Β) and (C) shown below were used to form the light-emitting layer. The measurement was performed at room temperature with a luminance of ❹500 (cd/m2). The luminance half-life of the current was driven. 6. In addition, the initial luminance after driving at a current density of 10 mA/cm 2 was measured. In the environment of 80 ° C, the brightness after continuous driving for 10 hours is shown in Table 9.

62 321016 200936567 [表9] Ο ❹62 321016 200936567 [Table 9] Ο ❹

亮度半衰壽命 (hr) 電流密度10mA/cm2 實施例 化合物 初期亮度 (cd/m2) 80°C、100時間後之亮遵 (cd/m2) 51 (1) &gt;1000 350 310 52 (2) &gt;1000 380 360 53 (3) &gt;1000 310 270 54 (4) &gt;1000 .400 370 55 (5) &gt;1000 350 300 56 (6) &gt;1000 410 370 57 (7) &gt;1000 370 340 58 (8) &gt;1000 380 340 59 (9) &gt;1000 360 330 60 (10) &gt;1000 380 350 61 (11). &gt;1000 350 270 62 (12) &gt;1000 420 380 63 (13) &gt;1000 360 290 64 (14) &gt;1000 410 360 65 〇5). &gt;1000 360 300 66 (16)、 &gt;1000 300 270 67 (17) &gt;1000 360 320 . 68 (18) &gt;1000 430 380 69 (19) &gt;1000 360 340 70 (20). &gt;1000 .380 360 71 (21) &gt;1000 370 300 72 (22) &gt;1000 360 310 73 (23). &gt;1000 400 310 74 (24) &gt;1000 390 310 75 (25) &gt;1000 360 320 76 (32) &gt;1000 400 360 77 (36) &gt;1000 430 390 78 (40) &gt;1000 450 400 79 (42) &gt;1000 420 360 80 (46) &gt;1000 430 370 比較例1 (Α) 180 90. 30 1 比較例2 ⑻ 160 50 〇 比較例3 (C) 350 110 50 I 63 321016 200936567 •. 由表9得知’本發明之化合物’任一者皆較使用比較 例之化合物（A)至（C)製作成之元件，壽命長且可得到高亮 度。 (實施例81) 在附有ΙΤ0電極之玻璃板上，將表2之ΗίΜ4真空蒸艘 而得到膜厚60nra之電洞注入層。接著，將表丨之化合物 與化合物（D)以100 : 5之紐成比進行共蒸鍍而形成膜厚 45nm之發光層。再蒸鍍化合物（Ε)而形成膜厚2〇nm之電子 ❹注入層。在其上’經由蒸鐘氧化鐘（L.i2〇)lnm，再蒸鐘Ai 10 Onm而形成陰極’而得到有機EL元件。此元件係在直流 電壓10V之外部量子效率顯示3.4%。此外，測定以發光 亮度500(cd/m2)進行定電流驅動後之亮度半衰壽命。此 外，測定以電流密度10mA/cm2驅動後之初期亮度、及在 8 0 °C之環境連續驅動1〇〇小時後之亮度。結果如表10所示。 . . - · · 'Luminance half-life (hr) Current density 10 mA/cm2 Initial luminance of the example compound (cd/m2) 80 °C, after 100 hours of light compliance (cd/m2) 51 (1) &gt;1000 350 310 52 (2) &gt;1000 380 360 53 (3) &gt;1000 310 270 54 (4) &gt;1000 .400 370 55 (5) &gt;1000 350 300 56 (6) &gt;1000 410 370 57 (7) &gt;1000 370 340 58 (8) &gt;1000 380 340 59 (9) &gt;1000 360 330 60 (10) &gt;1000 380 350 61 (11). &gt;1000 350 270 62 (12) &gt;1000 420 380 63 (13 ) &gt;1000 360 290 64 (14) &gt;1000 410 360 65 〇5). &gt;1000 360 300 66 (16), &gt;1000 300 270 67 (17) &gt;1000 360 320 . 68 (18) &gt ;1000 430 380 69 (19) &gt;1000 360 340 70 (20). &gt;1000 .380 360 71 (21) &gt;1000 370 300 72 (22) &gt;1000 360 310 73 (23). &gt;1000 400 310 74 (24) &gt;1000 390 310 75 (25) &gt;1000 360 320 76 (32) &gt;1000 400 360 77 (36) &gt;1000 430 390 78 (40) &gt;1000 450 400 79 (42 &gt;1000 420 360 80 (46) &gt;1000 430 370 Comparative Example 1 (Α) 180 90. 30 1 Comparative Example 2 (8) 160 50 〇Comparative Example 3 (C) 350 110 50 I 63 32 1016 200936567 • It is known from Table 9 that any of the "compounds of the present invention" is produced by using the components (A) to (C) of the comparative examples, and has a long life and high brightness. (Example 81) On a glass plate with a ΙΤ0 electrode, a vacuum injection vessel of a thickness of 60 nra was obtained by vacuum-steaming the steel of Table 2. Next, the compound of the watch and the compound (D) were co-deposited at a ratio of 100:5 to form a light-emitting layer having a thickness of 45 nm. Further, the compound (Ε) was vapor-deposited to form an electron-injecting layer having a film thickness of 2 〇 nm. On top of this, an organic EL device was obtained by forming a cathode by a steaming clock (L.i2) lnm and then a clock Ai 10 Onm. This component exhibits an external quantum efficiency of 3.4% at a DC voltage of 10V. Further, the luminance half life after driving with a constant current of 500 (cd/m2) was measured. Further, the initial luminance after driving at a current density of 10 mA/cm 2 and the luminance after continuous driving for one hour in an environment of 80 ° C were measured. The results are shown in Table 10. . . - · · '

化合物&lt;D&gt; ⑻ (實施例82至100) 除了傈用表1中之化合物取代化合物(1)以外，其餘與 實施例81同樣製作成元.件。此等元件在直流電壓10V之外 部量子效率任一者皆顯示3%以上。此外，測定以發光亮 度500(cd/m2)進行定電流驅動後之亮度半衰壽命。此外， 321016 64 200936567 測定以電流密度10mA/cm2驅動後之初期亮度、及在80°C 之環境連續驅動100小時後之亮度。結果如表10所示。. (比較例4至6) 除了使用化合物（A)至（C)取代化合物（1)以外，其餘與 實施例81同樣製作成元件。測定以發光亮度500(cd/m2) 在室溫將此等元件進行定電流驅動後之亮度半衰壽命。此 外，測定以電流密度lOmA/cm2驅動後之初期亮度、及在 80°C之環境連續騍動100小時後之亮度。結果如表10所示。Compound &lt;D&gt; (8) (Examples 82 to 100) An element was produced in the same manner as in Example 81 except that the compound of Table 1 was used instead of the compound (1). These components exhibit 3% or more of any quantum efficiency outside the DC voltage of 10V. Further, the luminance half life after driving with a constant current of 500 (cd/m2) was measured. Further, 321016 64 200936567 The initial luminance after driving at a current density of 10 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 80 ° C were measured. The results are shown in Table 10. (Comparative Examples 4 to 6) An element was produced in the same manner as in Example 81 except that the compound (A) to (C) were used instead of the compound (1). The luminance half life of the elements was measured by a constant current of 500 (cd/m2) at room temperature. Further, the initial luminance after driving at a current density of 10 mA/cm 2 and the luminance after continuous shaking for 100 hours in an environment of 80 ° C were measured. The results are shown in Table 10.

65 321016 200936567 -[表 ίο]65 321016 200936567 -[Table ίο]

實施例 化合爲 亮度半衰壽命 (hr) 電流密度10mA/cm2 初期亮度 (cd/m2) -80°C、Ϊ00時間後之亮度 (cd/m2) 81 (1) &gt;1000 360 320 82 (2) &gt;1000 330 290 83 (3) &gt;1000 390 320 84 (4) &gt;1000 400 320 85 (6) &gt;1000 410 350 86 (8) &gt;1000 320 260 87 (12) &gt;1000 400 350 88 (15) ：&gt;1000 360 320 89 (16) &gt;1000 380 310 90 (17) &gt;1000 400 340 91 (18) &gt;1000 • 360 300 92 (19). &gt;1000 . 320 310 93 (21) &gt;1000 320 280 94 (22) &gt;1000 350 300 95 .(24) &gt;1000 380 320 96 (33) &gt;1000 360 300 97 (38) &gt;1000 390 310 98 (41) &gt;1000 400 340 99 (45) &gt;1000 ; 420 400 100 (49) &gt;1000 . 390 360 比較合】4 (A) 250 120 90 比較例'5 (B) 160 80 0 比較例6 (G) 200 110 50 由表10得知，本發明之化合物，任一者皆較使用比較 例之化合物(A)至（C)製作成之元件，壽命長且可得到高亮 度。..: (實施例101) 在附有ITO電極之玻璃板上，將表2之HIM9真空蒸鍍 66 321016 200936567 * · .而得到膜厚60nm之電洞注入層。接著，將化合物（F)與表 1之化合物⑴以100 : 3之重量組成比進行共蒸鍍而形成: 膜厚45nm之發光層。再蒸鍍化合物（G)而形成膜厚別咖之 電子年入層。在其上，經由蒸鍍Li们nm，再蒸鍵A1進⑽ 而形成陰極，而得到有機EL元件。此元件係在直流電壓 10V之外部量子效率顯示3.:5%。此外，測定以發光亮度 500(Cd/m2)進行定電流驅動後之亮度半衰壽命。此外，$ ❹定以電流密度l〇mA/cm2驅動後之初期亮度、及在8〇。〇之 環境連續驅動100小時後之亮度。結果如表1丨所示。Example combination is luminance half life (hr) current density 10 mA/cm2 initial luminance (cd/m2) -80 °C, luminance after 00 00 (cd/m2) 81 (1) &gt;1000 360 320 82 (2 &gt;1000 330 290 83 (3) &gt;1000 390 320 84 (4) &gt;1000 400 320 85 (6) &gt;1000 410 350 86 (8) &gt;1000 320 260 87 (12) &gt;1000 400 350 88 (15) :&gt;1000 360 320 89 (16) &gt;1000 380 310 90 (17) &gt;1000 400 340 91 (18) &gt;1000 • 360 300 92 (19). &gt;1000 . 320 310 93 (21) &gt;1000 320 280 94 (22) &gt;1000 350 300 95 .(24) &gt;1000 380 320 96 (33) &gt;1000 360 300 97 (38) &gt;1000 390 310 98 (41) &gt;1000 400 340 99 (45) &gt;1000 ; 420 400 100 (49) &gt;1000 . 390 360 Comparison 4 (A) 250 120 90 Comparative Example '5 (B) 160 80 0 Comparative Example 6 (G 200 110 50 It is known from Table 10 that any of the compounds of the present invention is produced by using the compounds (A) to (C) of the comparative examples, and has a long life and high brightness. ..: (Example 101) On a glass plate with an ITO electrode, a hole injection layer having a film thickness of 60 nm was obtained by vacuum-depositing HIM9 of Table 2 by 66 321016 200936567*. Next, the compound (F) and the compound (1) of Table 1 were co-deposited at a weight ratio of 100:3 to form a light-emitting layer having a film thickness of 45 nm. Further, the compound (G) is vapor-deposited to form an electron-in-situ layer of a film thickness. On top of this, an organic EL element was obtained by vapor-depositing Li and re-steaming the bond A1 into (10) to form a cathode. This component exhibits an external quantum efficiency of 3.5% at a DC voltage of 10V. Further, the luminance half life after driving with a constant current of 500 (Cd/m2) was measured. In addition, the initial brightness after driving at a current density of l 〇 mA/cm 2 is set at 8 〇. The environment is continuously driven for 100 hours. The results are shown in Table 1.

(實施例T02至115) 除了使用表1中之化合物取代化合物（1)以外，其餘與 實施例101同樣製作成元件。此等元件在直流電壓ιόν之 外部量子效率任一者皆顯示3V以上，此外，測定以發光 亮度5 00 (cd/ m2)進行定1：流驅動後之亮度半衰壽命。此 ... · 外，測定以電流密度10mA/cm2驅動後之初期亮度、及在 80°C之環境連續驅動100小時後之亮度。結果如表π所示。 (比较例7至9) 除了使用化合物（A)至（C)取代化合物（1)以外，其餘與 67 321016 200936567 ' 實施例101同樣製作成元件。測定以發光亮度500(cd/m2) 在室溫將此等元件進行定電流驅動後之亮度半衰壽命。.此 外，測定以電流密度lOmA/cm2驅動後之初期亮度、及在 80°C之環境連讀驅動1〇〇小時後之亮度。結果如表11所示。 [表 11 ] ❹ ❹ 實施例 化合物 亮度半衰壽命 (hr) '.電流密度10mA/cm2 初期亮度 (cd/m2) 80°C、100時間後之亮度 (cd/m2) 101 (1) &gt;1000 420 310 102 (2) &gt;1000 360 320 103 ⑷ &gt;1000 350 .. 290 104 (8) &gt;1000 410 350 105 (9) .&gt;1000 : 380 320 106 (1.2) &gt;1000 360 ' 300 107 (14) &gt;1000 370 290. 108 (17). &gt;1000 350 320 109 (19) &gt;1000 390 320 110 ； (23). &gt;1000 410 . 370 111 (34) &gt;1000 400 ： 360 112 (37) -&gt;1000 420 370 113 (40) &gt;1000 390 340 114 (47) &gt;1000 360 330 . 115 (50) &gt;1000 400 380 比較例7 CA) 250 70 0 比較例8 (B) 100 60 0 比較例9 (C) 180 .90 30 由表11得知，本發明之化合物，任一者皆較使用比車交 例之化合物（A)至（C)製作成之元件，壽命長且可得到高亮 度。 (實施例116) 68 321016 200936567 . 在經洗淨之附有ΙΤ0電極之玻璃板上，將表3之HTM8 真空蒸鍍而得到膜厚6〇ηπι之電洞注入層。接著，將本發明 之表1中之化合物（1)真空蒸鍍而得到膜厚60nm之電子輸 送性發光層。在其上首先蒸鍍氟化鋰lnm，接著蒸鍵A1 200nm而形成電極，得到有機EL元件。此元件係在8V顯 示發光亮度600(cd/m2)之藍色發光。 .(實施例117) ..... -. . · ,(Examples T02 to 115) An element was produced in the same manner as in Example 101 except that the compound (Table 1) was used instead of the compound (1). These elements exhibit 3V or more in the external quantum efficiency of the DC voltage ιόν, and the luminance half life of the current after the flow-driving is determined by the light-emitting luminance of 500 cd (cd/m2). In addition, the initial luminance after driving at a current density of 10 mA/cm 2 and the luminance after continuous driving for 100 hours in an environment of 80 ° C were measured. The results are shown in Table π. (Comparative Examples 7 to 9) An element was produced in the same manner as in Example 101, except that the compound (A) to (C) were used instead of the compound (1). The luminance half life of the elements was measured by a constant current of 500 (cd/m2) at room temperature. Further, the initial luminance after driving at a current density of 10 mA/cm 2 and the luminance after driving for 1 hour in an environment of 80 ° C were measured. The results are shown in Table 11. [Table 11] ❹ 实施 Example compound brightness half life (hr) '. Current density 10 mA/cm2 Initial brightness (cd/m2) 80 ° C, brightness after 100 hours (cd/m2) 101 (1) &gt; 1000 420 310 102 (2) &gt;1000 360 320 103 (4) &gt;1000 350 .. 290 104 (8) &gt;1000 410 350 105 (9) .&gt;1000 : 380 320 106 (1.2) &gt;1000 360 ' 300 107 (14) &gt;1000 370 290. 108 (17). &gt;1000 350 320 109 (19) &gt;1000 390 320 110 ; (23). &gt;1000 410 . 370 111 (34) &gt;1000 400 : 360 112 (37) -&gt;1000 420 370 113 (40) &gt;1000 390 340 114 (47) &gt;1000 360 330 . 115 (50) &gt;1000 400 380 Comparative Example 7 CA) 250 70 0 Comparative Example 8 (B) 100 60 0 Comparative Example 9 (C) 180 .90 30 It is known from Table 11 that any of the compounds of the present invention is prepared using compounds (A) to (C) which are more specific than those of the car. The component has a long life and high brightness. (Example 116) 68 321016 200936567. On the washed glass plate with the ΙΤ0 electrode, HTM8 of Table 3 was vacuum-deposited to obtain a hole injection layer having a film thickness of 6 〇ηπ. Then, the compound (1) in Table 1 of the present invention was vacuum-deposited to obtain an electron-transporting light-emitting layer having a film thickness of 60 nm. On this, an electrode of lithium fluoride was first vapor-deposited, and then an electrode was formed by vapor-bonding A1 to 200 nm to obtain an organic EL device. This component emits blue light at an 8V display luminance of 600 (cd/m2). (Example 117) ..... -. .

在經洗淨之附有IT0電極之玻璃板上，將PED0T/PSS 〇 (聚（3, 4-伸乙基二氧）”2, 5-σ塞吩/聚苯乙稀績酸）依旋轉 .塗佈法製成60nm厚度之膜。並且，使表〗之化合物（7)與 化合物（H)以98 : 2之組成比溶於甲苯溶劑中並以旋轉塗佈 法塗佈，而製作成膜厚50nm之發光層。於此塗佈基板上再 依真空祭鍵法瘵錄（G)而形成膜厚2〇nm之電子注入層。在 其上’經由蒸鑛LhO inm ’再蒸鍍人11〇〇11111而形成陰極， : · ........ 得到有機EL元件。此元件係在8V顯示發光亮度乃晰以、2) ❹之藍邑發光，其色度係x=：() 16,y=0, Q5。以發光亮度500 : (cd/ m2)在室溫將此元件進行定電流驅動後之亮度半衰壽 命為1000小時以上。 • · - . · . ·PED0T/PSS 〇(poly(3,4-extended ethyldioxy) 2,5 σ phenophene/polystyrene) is rotated on a washed glass plate with an ITO electrode A film having a thickness of 60 nm was formed by a coating method, and a compound (7) of the above formula and a compound (H) were dissolved in a toluene solvent at a composition ratio of 98:2 and coated by a spin coating method to prepare a film. An illuminating layer having a film thickness of 50 nm. On the coated substrate, an electron injecting layer having a thickness of 2 〇 nm was formed by a vacuum bonding method (G), on which a person was re-evaporated via a vaporized LhO inm ' 11〇〇11111 to form a cathode, : ·........ Obtain an organic EL element. This element is shown in 8V to show the brightness of the light, and 2) the blue light of the ,, its color is x=: () 16, y = 0, Q5. With a luminance of 500: (cd/m2), the luminance half-life of the device after constant current driving at room temperature is 1000 hours or more. • · - .

(實施例118) 321016 69 200936567 ♦ * 除了使用表1中之化合物（9)取代化合物（7)以外，其 餘與實施例82同樣製作成元件。以發光亮度500(cd/m2) 在至溫將此_元件進行定電.旅驅動後之亮度半衰壽命皆為 1000小時以上。 - -. ' ...... (實施例119) - .. · ... - ... ι 在經洗淨之附有ITO電極之玻璃板上，蒸鍍銅酞菁素 而形成膜厚25nm之電洞注入層。揍著’將表1之化合物（7) 與化合物（I)以100 : 3之組成比進行共蒸鍍而形成膜厚 45mn之發光層：再蒸鍍(G)雨形成膜厚2〇咖之電洞阻擋 層》在其上，再將Alq3真空蒸鍍而製作成膜厚J〇nm之電 子注人型發光層，並在其上首先蒸鐘氟化鋰，接著蒸 .鍍A1 200nm兩形成電極’得到有機虹元件。以發光亮度： 50G(cd/m2)在室溫將此元件進行定電流驅彰後之亮度半 衰壽命為1000小時以上。(Example 118) 321016 69 200936567 ♦ * An element was produced in the same manner as in Example 82 except that the compound (9) in Table 1 was used instead of the compound (7). The _ component is set at a temperature of 500 (cd/m2) to the temperature. The half life of the luminance after driving is 1000 hours or more. - -. ' (Example 119) - .. · ... - ... ι On the glass plate with the ITO electrode washed, vapor-deposited copper phthalocyanine to form a film A 25 nm thick hole injection layer. Next, 'the compound (7) of Table 1 and the compound (I) were co-deposited at a composition ratio of 100:3 to form a light-emitting layer having a film thickness of 45 nm: re-evaporation (G) rain to form a film thickness of 2 The hole blocking layer is formed thereon, and then Alq3 is vacuum-deposited to form an electron-injecting type light-emitting layer having a film thickness of J〇nm, and firstly, lithium fluoride is vaporized thereon, followed by evaporation, and plating of A1 200 nm is formed. The electrode 'obtains an organic rainbow element. Luminance: 50G (cd/m2) The brightness half-life of the device after constant current driving at room temperature is 1000 hours or more.

(實施例120) 在經洗淨之附有ITO電極之玻璃板上，蒸鍍表2之化 合物（HIM2)而形成膜厚3〇nm之電洞注入層。接著，蒸⑮表 1之化合物（6)而形成膜厚20nm之電洞輸送層，再蒸鏡化 合物（F)而形成膜厚30nm之發光層。在其上，再將化二物 321016 200936567 « ，（G)真空蒸鍍而製作成膜厚30nm之電子注入層，並在其上 首先蒸鍍氟.化鋰lnm ’接著蒸鍍A1 200nm而形成電極，得 到有機EL元件。以發光亮度500(cd/m2)在室溫將此元件 進行定電流驅動後之亮度半衰壽命為1000小時以上。 (實施例121) . . · . ； · 在附有ITO電極之玻璃板上，將表2之HIM3真空蒸鐘 而得到膜厚60nm之電洞注入層。接著，將表1之化合物⑴ ❹與化合物（H)以100 : 5之紐成比進行共蒸鍍而形成膜厚 40nm之發光層。再蒸鍍化合物（G)而形成膜厚20nm之電子 注入層。香其上’經由蒸鍍氟化鐘5nm ’再蒸錄lOOnm 而形成陰極，得到有機EL元件。此元件係在8V顯示發光 亮度7000(Cd/m2)之藍色發光，其色度係〇. le，y = 0. 05。測定使此元件以發光亮度丨卯^^^發光後之艇 動電壓、與在80°C之環境連續驅動100小時後之亮度。結 果如表12.所示。 .. * ； . * © (實施例122至.132) 除了使用表1中之化合物取代化合物（1)以外，其餘與 實施例121同樣製作成元件。此等元件係在㈣顯示藍色發 光，其色度係x=0.16，y=0.〇5。測定使此等元件以發光 亮度l〇〇〇(cd/in2)發光後之魏動電壓、與在8〇。匸之環境連 續驅動100小時後之亮度。結果如表12.所示。 (比較例10至12) 除了使用化合物（A)至（C)取代化合物〇)以外，其餘與 實施例121同樣製作成元件。測定使此等元件以發光亮度 321016 71 200936567 1000(.cd/m2)發光後之軀動電壓、與在.。 ' 動1〇〇小時後之亮度。結果如表12听^800之環境連續驅 [表 12](Example 120) On the washed glass plate with the ITO electrode, the compound of Table 2 (HIM2) was vapor-deposited to form a hole injection layer having a film thickness of 3 〇 nm. Subsequently, the compound (6) of Table 1 was evaporated to form a hole transport layer having a film thickness of 20 nm, and the mirror compound (F) was further evaporated to form a light-emitting layer having a film thickness of 30 nm. On the other hand, the second material 3210016 200936567 « , (G) was vacuum-deposited to form an electron injecting layer having a film thickness of 30 nm, and firstly, vapor-deposited lithium lithium oxide 1 nm was formed thereon, followed by vapor deposition of A1 200 nm. Electrode to obtain an organic EL element. The luminance half life of the device after constant current driving at a room temperature of 500 (cd/m2) was 1000 hours or more. (Example 121) On the glass plate with the ITO electrode, the HIM3 of Table 2 was vacuum-steamed to obtain a hole injection layer having a film thickness of 60 nm. Next, the compound (1) of Table 1 and the compound (H) were co-deposited at a ratio of 100:5 to form a light-emitting layer having a film thickness of 40 nm. Further, the compound (G) was evaporated to form an electron injecting layer having a film thickness of 20 nm. On the scent, a cathode was formed by re-steaming 100 nm through a vapor deposition fluorination clock 5 nm to obtain an organic EL device. This component is a blue light emitting light having an illuminance of 7000 (Cd/m2) at 8V, and its chromaticity system is le. le, y = 0.05. The boat voltage after the light-emitting luminance of the element was measured and the brightness was continuously driven for 100 hours in an environment of 80 ° C. The results are shown in Table 12. .. *; . * © (Examples 122 to 132) An element was produced in the same manner as in Example 121 except that the compound (Table 1) was used instead of the compound (1). These elements are shown in (4) as blue light with a chromaticity of x=0.16 and y=0.〇5. The Wei dynamic voltage after the light emission of these elements was measured by the light-emitting luminance l 〇〇〇 (cd/in 2 ) was measured at 8 〇. The environment is continuously driven for 100 hours. The results are shown in Table 12. (Comparative Examples 10 to 12) An element was produced in the same manner as in Example 121 except that the compound (A) to (C) was used instead of the compound 〇). The body voltage of these elements was measured by the light-emitting luminance of 321016 71 200936567 1000 (.cd/m2). 'The brightness after 1 hour. The results are shown in Table 12, listening to the environmental continuous drive of [800] [Table 12]

化合物，即可製作成高性能之EL元件。且明顯地相對於比 較化合物發揮更高的性能，而可達成有機EL元件之低驅動 電壓化、長壽命化、色純度高的藍色發光。 【圖式簡單說明】. 第1圖係化合物（1)之爪光譜。（甲苯溶劑中） 321016 72 Ο 200936567 第2圖係化合物（1)之PL光譜。 第3圖係化合物（11)之UV光譜《 第4圖係化合物（11)之PL光譜&lt;= 第5圖係化合物（20)之UV光譜。 第6圖係化合物（20)之PL光譜。 第7圖係化合物（32)之UV光譜。 第8圖係化合物（32)之PL光譜。 【主要元件符號說明】 : 無0 〇 (甲苯溶劑中） (甲苯溶劑中） (甲苯溶劑中) (甲苯溶劑中） (甲苯溶劑中） (甲苯溶劑中） (甲苯溶劑中） 321016 73The compound can be made into a high-performance EL element. Further, it is possible to achieve higher performance with respect to the comparative compound, and it is possible to achieve blue light emission with low driving voltage, long life, and high color purity of the organic EL element. [Simplified description of the drawing]. Fig. 1 shows the claw spectrum of the compound (1). (in toluene solvent) 321016 72 Ο 200936567 Fig. 2 is a PL spectrum of the compound (1). Fig. 3 is a UV spectrum of the compound (11) "Fig. 4 is a PL spectrum of the compound (11) &lt;= Fig. 5 is a UV spectrum of the compound (20). Figure 6 is a PL spectrum of the compound (20). Figure 7 is a UV spectrum of the compound (32). Figure 8 is a PL spectrum of the compound (32). [Explanation of main component symbols] : None 0 〇 (in toluene solvent) (in toluene solvent) (in toluene solvent) (in toluene solvent) (in toluene solvent) (in toluene solvent) (in toluene solvent) 321016 73

Claims (1)

200936567 七、申請專利範圍： 1. 一種具有咔唑基之化合物，係如下逑通式[幻所示·· 通式[1]200936567 VII. Scope of application for patents: 1. A compound having a carbazolyl group, which is represented by the following formula: [Magic shown] Formula [1] R2 R3 . · . . . · • · · .· . (式中..，·Α表.示_下述通式..[2]所示之味嗓基.· . ❹ R1至R9分別獨立地表示氳原子、鹵素原子、取代或未取 代之1價蟑肪族烴基、取代或未取代之1價芳香族烴 基、取代或未取代之1價脂肪族雜環基、取代或未取代 之1價芳香族雜環基、氰基、烧氧基、芳氧基、烷硫基、 芳硫基、取代胺基、醯基、羰義、芳氧裁基、烧確 醯基、或芳磺醯基） . . .... . ▲ ·R2 R3 . · . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Is a halogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aliphatic heterocyclic group, a substituted or unsubstituted 1 Aromatic heterocyclic group, cyano group, alkoxy group, aryloxy group, alkylthio group, arylthio group, substituted amine group, fluorenyl group, carbonyl group, aryloxy group, decyl group, or aryl sulfonate Base) . . . . . ▲ · (式中，Ar表示取代或未取代之償族基、 取代或，取代之.Γ價芳香族_^^ R1。至R /分別獨立地表示氫原子、齒素原子、取代或未 取代之1價騎錢基、取代或未取代之丨價芳香族趣 基、取代或未取代之1價腊肪埃雜環基、取代或未取代 . · - 321〇16 200936567 芳香族雜環基、氰基、燒氧基、芳氧基、燒峻Λ =基、取代胺基、_、絲躲、芳輪基、^ 醯基、或芳確醯基）。 ' . 只 2. 1申睛專利範圍第工項之具有味唾基之化合物，其中， R係下述通式[3]所示之取代或未取代之苯基者^ ’ • ’通式[3.](wherein, Ar represents a substituted or unsubstituted fultyl group, substituted or substituted, valence aromatic _^^ R1. To R / independently represents a hydrogen atom, a dentate atom, a substituted or unsubstituted 1 A valence, substituted or unsubstituted fluorene, a substituted or unsubstituted monovalent, heterocyclic, substituted or unsubstituted. · - 321〇16 200936567 Aromatic heterocyclic, cyano , alkoxy, aryloxy, burnt Λ = base, substituted amine, _, silk, aromatic, sulfhydryl, or aryl. '. A compound having a taste of a saliva group according to the work item of the second paragraph of the patent application, wherein R is a substituted or unsubstituted phenyl group represented by the following general formula [3] ^ ' 3.] © (式令R至R分別獨立地表示氫原子、齒棄原 取代或未取代之1償脂肪族煙基、取代或未取代之% :谭芳香族烴基、取代或未取代之.】償脂肪族雜環基、取 :.代或未取代冬十價芳香族雜環基、氰基、烷氧基、芳氧 棊、炫硫蓦、芳硫基、取代胺基、醯基、院氧羰基、芳 h :氧羰基丨碑磺醯基’或芳磺醯基’^至以可於各個相 〇 .鄰之取代基間形成環）。: 3·七:申請專利範圍拿1項或第2項之具有咔唑墓之化合 物’其中，Ar1係取代或未取蚱之碳數6至Ϊ8之1價芳 香族烴基、或是取代或未取代之碳數2莖18之1價芳 :香族雜環基者。.’ ' 4.如申請專利範圍第.1項至第3項中任一項之具有咩唑基· 之化合物，其中，Ar1係下述通式[4]所示之取代或未取 代之笨基者：： 321016 75 200936567 0 ^ 通式[4]© (Formula R to R independently represent a hydrogen atom, agglomerated or unsubstituted 1 aliquot of an aliphatic group, substituted or unsubstituted %: tan aromatic hydrocarbon group, substituted or unsubstituted.) a heterocyclic group of: a substituted or unsubstituted winter ten-valent aromatic heterocyclic group, a cyano group, an alkoxy group, an aryloxy sulfonium group, a thiol sulfonium group, an arylthio group, a substituted amine group, a fluorenyl group, a oxycarbonyl group , aryl h: oxycarbonyl oxime sulfonyl ' or aryl sulfonyl '^ to form a ring between the substituents of each phase. : 3·7: The scope of the patent application is 1 or 2 of the compounds with oxazolium tombs. Among them, Ar1 is substituted or unreacted with a carbon number of 6 to 8 of a monovalent aromatic hydrocarbon group, or substituted or not. Substituted carbon number 2 Stem 18 of 1 valence: Fragrant heterocyclic group. The compound having a carbazolyl group according to any one of the items 1 to 3, wherein Ar1 is a substituted or unsubstituted stupid represented by the following formula [4] Base:: 321016 75 200936567 0 ^ General Formula [4] (式中，R22至R26分別獨立地表示氫原子、鹵素原子、 取代或未取代之1價脂肪族烴基、取代或未取代之1 價芳香族烴基、取代或未取代之1價脂肪族雜環基、取 代或未取代之1價芳香族雜環基、氰基、烷氧基、芳氧 基、烷硫基、芳硫基、取代胺基、醯基、烷氧羰基、芳 氧羰基、烷磺醯基、或芳磺醯基）。 5. 如申請專利範圍第1項至第4項中任一項之具有咔唑基 之化合物，其中，R1(l至R16係氫原子者。 6. —種有機電激發光元件甩材料，係含有申請專利範圍第 1項至第5項中任一項之具有咔唑基之化合物而成。 7. —種有機電激發光元件，係於一對電極間形成複數層有 • · 〇 機層而成之有機電激發光元件，其中，前述有機層之至 少一層係含有申請專利範圍第6項之有機電激發光元 件用材料而成。： 8. —種有機電激發光元件，係於一對電極間形成發光層或 包含發光層之複數層有機層而成之有機電激發米元 件，其中，前述發光層係含有申請專利範圍第6項之有 機電激發光元件用材料而成。. 9.如申請專利範圍第8項之有機電激發光元件，其中，在 76 321016 200936567 - 發光層中復含有磷光發光材料而成者。 10.如申請專利範圍第8項或第9項之有機電激發光元件， 其中，.發光層係藉由塗佈而成膜所成者。 〇 77 321016(wherein R22 to R26 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted monovalent aliphatic hydrocarbon group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, a substituted or unsubstituted monovalent aliphatic heterocyclic ring 1, substituted or unsubstituted monovalent aromatic heterocyclic group, cyano group, alkoxy group, aryloxy group, alkylthio group, arylthio group, substituted amine group, mercapto group, alkoxycarbonyl group, aryloxycarbonyl group, alkane Sulfonyl, or arylsulfonyl). 5. A compound having a carbazolyl group according to any one of claims 1 to 4, wherein R1 (1 to R16 is a hydrogen atom). 6. Organic electroluminescent device 甩 material, A compound having a carbazolyl group according to any one of claims 1 to 5. 7. An organic electroluminescent device which is formed by forming a plurality of layers between a pair of electrodes. The organic electroluminescent device is characterized in that at least one layer of the organic layer is made of a material for an organic electroluminescence device of claim 6: 8. An organic electroluminescence device is used in one An organic electroluminescence element comprising a light-emitting layer or a plurality of organic layers including a light-emitting layer, wherein the light-emitting layer comprises a material for an organic electroluminescence device according to claim 6 of the patent application. 9 An organic electroluminescent device according to claim 8 of the patent application, wherein the phosphorescent luminescent material is further contained in the luminescent layer of 76 321016 200936567. 10. The organic electric device according to claim 8 or 9 Excitation light element , Wherein the light emitting layer by coating a film formation system to those. Square 77321016
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