TW201113238A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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TW201113238A
TW201113238A TW099125878A TW99125878A TW201113238A TW 201113238 A TW201113238 A TW 201113238A TW 099125878 A TW099125878 A TW 099125878A TW 99125878 A TW99125878 A TW 99125878A TW 201113238 A TW201113238 A TW 201113238A
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aryl
alkyl
compound
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TW099125878A
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Chi-Sik Kim
Young-Jun Cho
Hyuck-Joo Kwon
Bong-Ok Kim
Sung-Min Kim
Seung-Soo Yoon
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Gracel Display Inc
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Abstract

Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound disclosed herein exhibits good luminescent efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

Description

201113238 Λ 六、發明說明： 【發明所屬之技術領域】 I發明係關於新穎有機電場發光（eleetrQlum鹏⑽t， EL)化合物及使用該化合物之有機電場發光裝置。本發明之 有機電場發光化合物係如化學式1所表示： 化學式1201113238 Λ VI. Description of the invention: [Technical field to which the invention pertains] The invention relates to a novel organic electric field luminescence (eleetrQlumpeng (10)t, EL) compound and an organic electric field illuminating device using the same. The organic electroluminescent compound of the present invention is represented by Chemical Formula 1: Chemical Formula 1

【先前技術】 =有機EL裝置中’決定其包括發光效率、操 專^的最重要的因素係電場發光材料。對電場發p 之一些要求包括於固態之高螢光量子產 ，、於真空沈積過程中的抗分解之抵抗,== 句勻薄臈的能力及安定性。 y成 (ΗαΓ/ΓΓ有機EL裝置一般具有陽極/電洞注入居 電洞傳輸層（HTL)/發储·(ΕΜυ/電子傳輪^ 電子注入層（EIL)/陰極之構型。取決 ’日 2料層陶可創造發藍色、綠色或紅==成發 先裴置。 有機電場發 材粗電場發光材料就功能方面可分為主體材料及換心 傾。通常，咸知藉由將摻雜劑摻雜主 ^ 有優異的EL特性。最近，開笋 1備之釭層具 置成為迫在眉睫的挑戰。尤其 之有機 3 9^96〇 201113238 咐EL性崎科，軸_為，開 發遇優越於傳統電場發光材料之材料。 對於綠色螢光材料而言，參（8—經基 係作為主體材料而棄一本/ I)(Alq)[Prior Art] = The most important factor in determining the luminous efficiency and the operation of the organic EL device is the electric field luminescent material. Some requirements for the electric field to emit p include high-fluorescence quantum production in the solid state, resistance to decomposition during vacuum deposition, and the ability and stability of the sentence. y into (ΗαΓ/ΓΓ organic EL device generally has an anode/hole injection into the hole transport layer (HTL) / storage · (ΕΜυ / electron transfer ^ electron injection layer (EIL) / cathode configuration. Depends on 'day 2 material layer pottery can create blue, green or red == into the hair first set. Organic electric field hair material rough electric field luminescent material can be divided into main material and change heart function. Usually, salty knows by blending The impurity doping main ^ has excellent EL characteristics. Recently, the opening of the bamboo shoots has become an imminent challenge. Especially the organic 3 9^96〇201113238 咐EL Sakiko, the axis _, the development is superior For materials of traditional electric field luminescent materials. For green fluorescent materials, the reference (8-base system as a host material and a copy of / I) (Alq)

蓉作；^ 财物、切晴生物、DPT 專作為摻雜劑，摻雜濃度為百分之幾至百 =場發光材料具有可商業化之初始發光效率，二 料間=降低。由於壽命問題，該等電場發光材 科難以用於尚性能、大尺寸面板中。 壽广二:要，可提供令人滿意之0⑽裝置之操作 奇命、更優異之蚊性及優越的性能之主體材料。 【發明内容】 技術問題 據此’本發明之-目的係提供比傳統材料更優異之發 及裝置操作壽命且具有帶適當色坐標之優異骨架之 有機電場發光化合物，以解決上述問題。本發明之另一目 的係提供使用該有機電場發光化合物作為電場發光材料之 有機電場發光裝置。 技術解決方案 一大體方面，本發明提供化學式1所表示之有機電場 發光化合物及使⑽化合物之有機電場發光裝置。由於本 發明之有機電場發光化合物具有優異發光效率及優里壽命 特性’因此其可祕製造具有非常_操作壽命之獅。 94960 4 201113238Rong Zuo; ^ Property, Chess, and DPT are used as dopants, and the doping concentration is several hundred to one hundred. The field luminescent material has a commercial initial luminous efficiency, and the ratio between the two materials is reduced. Due to the longevity problem, these electric field luminescent materials are difficult to use in panels of high performance and large size. Shouguang 2: To provide a satisfactory material for the operation of the 0(10) device, the superiority of the mosquito, and the superior performance of the material. DISCLOSURE OF THE INVENTION Technical Problem According to the present invention, an object of the present invention is to provide an organic electroluminescent compound having an excellent performance and device operating life superior to conventional materials and having an excellent skeleton with appropriate color coordinates to solve the above problems. Another object of the present invention is to provide an organic electric field light-emitting device using the organic electroluminescent compound as an electric field luminescent material. Technical Solution In a broad aspect, the present invention provides an organic electric field luminescent compound represented by Chemical Formula 1 and an organic electric field illuminating device using the compound (10). Since the organic electroluminescent compound of the present invention has excellent luminous efficiency and excellent life characteristics, it is possible to manufacture a lion having a very long operational life. 94960 4 201113238

A 化學式1A chemical formula 1

其中URu獨立表示氫U素、具有或不 取代基之（CK3G)烧基、具有或不具有取代基之（c6_ 芳基、與—個或多個具有或不具有取代基之（C3-C30)環燒 基稠合之經取代或未經取代2(C6_C3〇)芳基、具有或不^ 有取，基之（C3-C3G)雜芳基、具有或不具有取代基之5員 至7員雜環烷基、與一個或多個具有或不具有取代基之芳 香環稠合之5員至7員雜環烷基、具有或不具有取代基2 (C3-C30)環烷基、與一個或多個具有或不具有取代基之芳 香環稠合之（C3-C30)環燒基、氰基、胺基、具有或不具有 取代基之（C1-C30)烷基胺基、具有或不具有取代基之 (C6-C30)芳基胺基、NR2iR22、BR23R24、PR25R26、p(=〇)r27R28、 RaRbReSi_、RdY-、ReC(=0)-、1^(=0)0-、具有或不具有取 代基之（C6-C30)芳基（C1-C30)烧基、具有或不具有取代基 之（C2-C30)烯基、具有或不具有取代基之（C2-C30)炔基、 具有或不具有取代基之（C6-C30)芳氧基羰基、具有或不具 有取代基之（C1-C30)烷氧基羰氧基、具有或不具有取代基 之（C1-C30)烷基羰氧基、具有或不具有取代基之（C6-C30) 芳基羰氧基、具有或不具有取代基之（C6-C30)芳氧基羰氧 5 94960 201113238 基、羧基、硝基、 ReiWherein URu independently represents hydrogen U, a (CK3G) group with or without a substituent, (c6_aryl, and one or more (C3-C30) with or without a substituent) a substituted or unsubstituted 2(C6_C3〇)aryl group with or without a cycloalkyl group, a (C3-C3G)heteroaryl group, 5 to 7 members with or without a substituent a heterocycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings having or without a substituent, with or without a substituent 2 (C3-C30) cycloalkyl group, and Or (C3-C30)cycloalkyl, cyano, amine, (C1-C30)alkylamino group with or without a substituent fused with or without a substituent, with or without (C6-C30) arylamino group having a substituent, NR2iR22, BR23R24, PR25R26, p(=〇)r27R28, RaRbReSi_, RdY-, ReC(=0)-, 1^(=0)0-, with or a (C6-C30) aryl (C1-C30) alkyl group having no substituent, a (C2-C30) alkenyl group having or not having a substituent, a (C2-C30) alkynyl group having or not having a substituent, With or without substituents (C6-C30 An aryloxycarbonyl group, a (C1-C30) alkoxycarbonyloxy group with or without a substituent, a (C1-C30)alkylcarbonyloxy group with or without a substituent, with or without a substituent (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy with or without a substituent 5 94960 201113238 base, carboxyl group, nitro group, Rei

或經基，或 者汜至Ru可各自經由具有或不具有稠合環之（C3_C3〇)伸 烷基或（C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或 單環或多環之芳香環； X、Y 及 W 獨立表示-(CR5lRs2)f、_(R51)C=C(R52)_、 、-ο-、-Si(R54)(R55)_、_P(R56)_、 P(-0)(^57)-、_C(=〇)-或 _B(R58)_ ;Or a trans group, or a ruthenium to Ru, each may be bonded to an adjacent substituent via a (C3_C3〇)alkyl group or a (C3-C30)alkyl group with or without a fused ring to form an alicyclic ring, or a single ring. Or a polycyclic aromatic ring; X, Y and W independently represent -(CR5lRs2)f, _(R51)C=C(R52)_, , -ο-, -Si(R54)(R55)_, _P(R56 )_, P(-0)(^57)-, _C(=〇)- or _B(R58)_ ;

Rs]至R58及R6!至R63係如L至Rl4所定義； 該雜環烷基或雜芳基可含有一個或多個選自B、N、〇、 s、P(=0)、Si及P之雜原子；以及 心至R28獨立表示具有或不具有取代基之（c卜C3〇)烷 基、具有或不具有取代基之（C6_C30)芳基或具有或不具有 取代基之（C3-C30)雜芳基；Rs] to R58 and R6! to R63 are as defined in L to Rl4; the heterocycloalkyl or heteroaryl group may contain one or more selected from the group consisting of B, N, 〇, s, P(=0), Si and a hetero atom of P; and a core to R28 independently representing a (c-C3〇)alkyl group with or without a substituent, a (C6_C30) aryl group with or without a substituent, or with or without a substituent (C3- C30) heteroaryl;

Ra、Rb、Re & Rd獨立表示具有或不具有取代基之（cn_c30；) 烧基或具有或不具有取代基之（C6_C3〇)芳基； Y表示S或0 ;Ra, Rb, Re & Rd independently represent (cn_c30;) alkyl group with or without a substituent (C6_C3〇) aryl group with or without a substituent; Y represents S or 0;

Re& Rf表示具有或不具有取代基之（C1-C30)烷基、具 有或不具有取代基之（C1-C30)烷氧基、具有或不具有取代 基之（C6-C30)芳基或具有或不具有取代基之（C6_C3〇)芳氧 基；以及 m表示整數1或2。 【實施方式】 6 94960 2〇lll3238 於本發明中，‘提基， 其， —、‘烷氧基，及其他含有‘卜 "部分之取代基包括直鏈及分支鏈基團兩種。 疋 ‘環烧基’包括具有或不具有取代基之产，明 有或不具有取代基之（叫3〇)雙環絲_。基及具 於本發明中，芳基，表示自芳香族烴 :所獲得之有機基且可包括4員至7員，特別是卓以 員，之早環或稠合環，包括藉由單鍵鍵聯之複數個芳基。 具體實例包括’但不限於苯基、萘基、聯苯基、葱基:節 基、第基、菲基、聯伸三笨基（triphenylenyl)、$基、^ 基、制基、稍四苯基（naphthacenyl)、丙二烯合第基 (fluoranthenyl)等。該萘基包括卜萘基及2-萘基，該； 基包括1-蒽基、2-蒽基及9-蒽基，該第基包括Ι-g基、 2-薙基、3 -苐基、4-苐基及9 -第基。於本發明中，‘雜芳 基’意指含有作爲芳香環骨架原子之1個至4個選自b、 N、0、S、P(=〇)、Si及p之雜原子以及為碳原子之其他剩 餘芳香環骨架原子之芳基。該雜芳基可為5員或6員單環 雜芳基或為與一個苯環縮合所得之多環雜芳基，並可為部 分飽和。此外，該雜芳基包括藉由單鍵鍵聯之多於—個之 雜芳基。該雜芳基包括二價芳基，其中於環上之雜原子可 經氧化或四級化以形成諸如N-氧化物或四級鹽。具體實例 包括’但不限於單環雜芳基，諸如呋喃基、噻吩基、吡哈 基、咪唑基、°比唑基、噻唑基、噻二唑基、異噻唑基、異 噚唑基、噚唑基、噚二唑基、三哄基、四畊基、三唑基、 四唑基、呋吖基、吡啶基、吡畊基、嘧啶基、嗒畊基等； 7 94960 201113238 多裱雜芳基，諸如苯并呋喃基、苯并噻吩基、異苯并呋喃 基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異卩等 唑基、苯并噚唑基、異吲哚基、、吲哚基、吲唑基、笨并噻 二唑基 '喹啉基、異喹啉基、噌啉基、喹唑啉基、喹卩等啉 基味坐基、啡α疋基及苯并二卩琴呢基（benz〇d i 〇χ〇 1 y 1 )等、 其相應的N-氧化物（例如吡啶基N_氧化物、喹啉基N_氧化 物等），其四級鹽，等。 於本發明中，“（C1-C30)烷基”可包括（C1-C20)烷基 或（ci-cio)烷基，“（C6_C30)芳基”包括（C6_C2〇)芳基或 (C6-C12)芳基。“（C3-C30)雜芳基，，包括（C3-C20)雜芳基 或（C3-C12)雜芳基，而“（C3—C3〇)環烷基，，包括（C3_C2〇) 環烷基或（C3-C7)環烷基。“（C2-C30)烯基或炔基”包括 (C2-C20)烯基或炔基、（C2_cl〇)烯基或炔基。 於具有或不具有取代基’ ’該取代基進一步經一個 或多個選自下列所組成群組之取代基取代：氘、函素、具 有或不具有_素取代基之（C1-C30)烷基、（C6-C30)芳基、 具有或不具有（C6-C30)芳基取代基之（C3-C30)雜芳基、含 有一個或多個選自B、N、0、S、P(=0)、Si及P之雜原子 之5員至7員雜環烷基、與一個或多個芳香環稠合之5員 至7貝雜環烧基、（C3-C30)環烧基、與一補或多個芳香環 稠合之（C3*~C30)環烷基、三（C1-C30)烷基矽烷基、二 (C1_C30)烷基（C6-C30)芳基矽烷基、三（C6-C30)芳基矽燒 基、（C2-C30)烯基、（C2-C30)炔基、氰基、咔唑基、NR31R32、 BR33R34、pb5R36、P(=〇)R37R38、（C6-C30)芳基（C1-C30)烷基、 δ 94960 201113238 (C1-C30)烷基（C6—C30)芳基、（cl_C3〇)烷氧基、（cl_C3〇) 烷硫基、（C6-C30)芳氧基、（C6-C30)芳硫基、（C1—C30)烷 氧基羰基、（C1-C30)烷基羰基、（C6-C30)芳基羰基、（C6-C30) 芳氧基羰基、（C1-C30)烷氧基羰氧基、（C1—C3〇)烷基羰氧 基、（C6-C30)芳基羰氧基、（C6-C30)芳氡基羰氧基、羧基、 硝基及赵基，或者該取代基鍵聯至相鄰取代基以形成環； 以及Re& Rf represents (C1-C30)alkyl with or without a substituent, (C1-C30) alkoxy group with or without a substituent, (C6-C30) aryl group with or without a substituent or (C6_C3〇) aryloxy group with or without a substituent; and m represents an integer of 1 or 2. [Embodiment] 6 94960 2〇lll3238 In the present invention, 'tackyl, its, —, 'alkoxy, and other substituents containing a 'bu" moiety include both straight-chain and branched-chain groups. ‘ 'Cycloalkyl group' includes the production of a double-ring yarn with or without a substituent, with or without a substituent. And in the present invention, an aryl group, represented by an aromatic hydrocarbon: an organic group obtained and which may include from 4 to 7 members, especially an expert, an early or fused ring, including by a single bond A plurality of aryl groups bonded together. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, onion: nodal group, benzyl, phenanthryl, triphenylenyl, benzyl, base, slightly tetraphenyl (naphthacenyl), fluoranthenyl, and the like. The naphthyl group includes a naphthyl group and a 2-naphthyl group, and the group includes a 1-fluorenyl group, a 2-fluorenyl group and a 9-fluorenyl group, and the group includes a fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, and 4 - 苐 base and 9 - base. In the present invention, 'heteroaryl' means one to four hetero atoms selected from the group consisting of b, N, 0, S, P (=〇), Si and p as an aromatic ring skeleton atom and are carbon atoms. The aryl group of the remaining remaining aromatic ring skeleton atoms. The heteroaryl group may be a 5- or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group obtained by condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl group includes more than one heteroaryl group bonded by a single bond. The heteroaryl group includes a divalent aryl group in which a hetero atom on the ring can be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include, but are not limited to, monocyclic heteroaryl groups such as furyl, thienyl, pyrhadyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, anthracene Azolyl, oxadiazolyl, tridecyl, tetra-negative, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridinyl, pyrimidinyl, hydrazine, etc.; 7 94960 201113238 Base, such as benzofuranyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoindole, etc., benzoxazolyl, iso Sulfhydryl, fluorenyl, carbazolyl, benzothiazolyl 'quinolinyl, isoquinolinyl, porphyrinyl, quinazolinyl, quinoxaline, etc. a benzodiazepine group (benz〇di 〇χ〇1 y 1 ), etc., corresponding N-oxides (eg, pyridyl N_oxide, quinolyl N-oxide, etc.), Grade salt, etc. In the present invention, "(C1-C30)alkyl" may include (C1-C20)alkyl or (ci-cio)alkyl, and "(C6_C30)aryl" includes (C6_C2〇)aryl or (C6- C12) aryl. "(C3-C30)heteroaryl, including (C3-C20)heteroaryl or (C3-C12)heteroaryl, and "(C3-C3〇)cycloalkyl, including (C3_C2〇)cycloalkane Or a (C3-C7) cycloalkyl group. "(C2-C30)alkenyl or alkynyl" includes (C2-C20)alkenyl or alkynyl, (C2_cl〇)alkenyl or alkynyl. The substituent is further substituted with one or more substituents selected from the group consisting of ruthenium, a cyclin, a (C1-C30) alkane having or without a _-substituent substituent, with or without a substituent. a (C6-C30) aryl group, a (C3-C30)heteroaryl group having or without a (C6-C30) aryl substituent, containing one or more selected from the group consisting of B, N, 0, S, P ( =0), a 5-member to 7-membered heterocycloalkyl group of a hetero atom of Si and P, a 5- to 7-membered heterocyclic group fused to one or more aromatic rings, (C3-C30) cycloalkyl, (C3*~C30)cycloalkyl, tri(C1-C30)alkyldecane, di(C1_C30)alkyl(C6-C30)aryldecyl, fused to one or more aromatic rings. C6-C30) arylsulfonyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, pb5R36, P(=〇)R37R38, (C6-C30 Aryl (C1-C30)alkyl, δ 94960 201113238 (C1-C30)alkyl (C6-C30) aryl, (cl_C3〇)alkoxy, (cl_C3〇)alkylthio, (C6-C30) Aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30) arylcarbonyl (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C3〇)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30 An arylcarbonylcarbonyl group, a carboxyl group, a nitro group, and a zeoliyl group, or the substituent is bonded to an adjacent substituent to form a ring;

Rsi至R38獨立表示（C1-C30)烷基、（C6-C30)芳基或 (C3-C30)雜芳基。Rsi to R38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.

Rl至Rl4、R21至R28、R51至R58及Rei至R63獨立選自，但 不限於：氫；氣；鹵素；烧基’如曱基、乙基、丙基、丁 基、戊基、己基、乙基己基、庚基、辛基等；芳基，如苯 基、奈基、苐基、聯苯基、菲基、聯三笨基（terphenyl)、 芘基、茈基、螺雙苐基（8口丨1'〇1^£1110『61^1)、丙二烯合苐 基、蒯基、聯伸三苯基等；與一個或多個環烷基稠合之芳 基，如 1,2-二苊基（1，2-dihydroacenaphthyl);雜芳基， 如二苯并噻吩基、二苯并呋喃基、咔唑基、吡啶基、呋喃 基、σ塞吩基、啥喊基、三哄基、σ密咬基、σ答哄基、啥曙琳 基、啡啉基等；與一個或多個芳香環稠合之雜環烷基，如 ^苯并°比洛咬基(^6112〇971'1'〇11(1丨]1〇)、[苯并六氫°比咬基 (benzopiperidino)、Ν-二笨并嗎琳基 (dibenzomorpholino)、N-二苯并氮呼（dibenzoazepino) 等；經芳基（如苯基、萘基、苐基、聯苯基、菲基、聯三苯 基、芘基、茈基、螺雙苐基、丙二烯合苐基、蒯基、聯伸 9 94960 201113238 三苯基等）或雜芳基（如二苯并β塞吩基、二苯并1*夫喃基、吟 〇坐基、°比咬基、吱喃基、°塞吩基、喧琳基、三哄基、°密〇定 基、嗒哄基、喹噚啉基、啡啉基等）取代之胺基；芳氧基， 如聯苯基氧基（biphenyloxy)等；芳硫基，如聯苯基硫基 (biphenylthio)等；芳烧基，如聯苯基曱基 (biphenylmethyl)、三苯基甲基（triphenylmethyl)等；R1 to R14, R21 to R28, R51 to R58 and Rei to R63 are independently selected from, but not limited to: hydrogen; gas; halogen; alkyl group such as mercapto, ethyl, propyl, butyl, pentyl, hexyl, Ethylhexyl, heptyl, octyl, etc.; aryl, such as phenyl, naphthyl, anthryl, biphenyl, phenanthryl, terphenyl, fluorenyl, fluorenyl, spirobiguanyl ( 8-port 丨1'〇1^£1110『61^1), propadienyl fluorenyl, fluorenyl, extended triphenyl, etc.; aryl group fused to one or more cycloalkyl groups, such as 1, 2 -1,2-dihydroacenaphthyl; heteroaryl, such as dibenzothiophenyl, dibenzofuranyl, oxazolyl, pyridyl, furyl, σ-sequenyl, sulphonyl, triterpene a heterocyclic alkyl group fused to one or more aromatic rings, such as a benzophene thiol base (^6112〇), a σ, a thiol group, a cylinyl group, a phenanthrenyl group, or the like. 971'1'〇11(1丨]1〇), [benzopiperidino, benzo-dibenzomorpholino, dibenzoazepino, etc. ; aryl group (such as phenyl, naphthyl, anthracenyl, biphenyl, phenanthryl, hydrazine Base, fluorenyl, fluorenyl, spirobiindyl, propadienyl fluorenyl, fluorenyl, co-extension 9 94960 201113238 triphenyl, etc.) or heteroaryl (eg dibenzo-β-thiophene, dibenzo 1*, 喃 基, 吟〇, °, 咬, 吱, 塞, 塞, 喧, 哄, 哄, 〇, 噚 、, quinolinyl, morpholinyl Equivalent to an amine group; an aryloxy group such as biphenyloxy; an arylthio group such as biphenylthio; and an aryl group such as biphenylmethyl , triphenylmethyl (triphenylmethyl), etc.;

—sc - -，且彼等基團可如化學式1所述 般進一步被取代。 更具體地，Rl至可藉由下列結構例示之，但不限於 此： 10 94960 201113238—sc — — and these groups can be further substituted as described in Chemical Formula 1. More specifically, R1 can be exemplified by the following structure, but is not limited to this: 10 94960 201113238

至Rl32獨立表示氫、氘、鹵素、（C卜C30)烷基、 (C6-C30)芳基、與一個或多個（C3-C30)環烷基稠合之 (C6-C30)芳基、（C3-C30)雜芳基、5員至7員雜環烷基、 與一個或多個芳香環稠合之5員至7員雜環烷基、（C3-C30) 環烷基、與一個或多個芳香環稠合之（C3-C30)環烷基、氰 基、胺基、（C1-C30)烷基胺基、（C6-C30)芳基胺基、NR41R42、 BR—44、PR45R46、P(=〇)R47R48、三（n-C30)烷基矽烷基、二 (C1-C30)烷基（C6-C30)芳基矽烷基、三（C6-C30)芳基矽院 基、（C6-C30)芳基（a-C30)烷基、（C1-C30)烷氧基、（C1-C30) 烷硫基' (C6-C30)芳氧基、（C6-C30)芳硫基、（C1-C30)院 11 94960 201113238 氧基k基、（C1-C30)烧基数基、（C6-C30)芳基艘基、（C2-C30) 烯基、（C2-C30)炔基、（C6-C30)芳氧基羰基、（cl_C3〇)烧 氧基幾氧基、（C1-C30)烧基毅氧基、（C6-C30)芳基裁氧基、 (C6-C30)芳氧基羰氧基、羧基、硝基或羥基；或者R?i至 Rm可經由具有或不具有稠合環之（C3_C3〇)伸烷基或 (C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環或單環或多 環之芳香環；以及 心至R48獨立表示（C1-C30)烷基、（C6-C30)芳基或 (C3-C30)雜芳基。To Rl32 independently represent hydrogen, deuterium, halogen, (C-C30) alkyl, (C6-C30) aryl, (C6-C30) aryl fused to one or more (C3-C30) cycloalkyl groups, (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused to one or more aromatic rings, (C3-C30)cycloalkyl, and Or a plurality of aromatic ring fused (C3-C30) cycloalkyl, cyano, amine, (C1-C30)alkylamino, (C6-C30) arylamine, NR41R42, BR-44, PR45R46 , P(=〇)R47R48, tris(n-C30)alkyldecylalkyl, di(C1-C30)alkyl(C6-C30)aryldecylalkyl, tris(C6-C30)arylfluorene, ( C6-C30) aryl (a-C30) alkyl, (C1-C30) alkoxy, (C1-C30) alkylthio '(C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) Institute 11 94960 201113238 Oxyk group, (C1-C30) alkyl group, (C6-C30) aryl, (C2-C30) alkenyl, (C2-C30) alkynyl, C6-C30) aryloxycarbonyl, (cl_C3〇)alkoxyoxy, (C1-C30)alkyloxy, (C6-C30)aryloxy, (C6-C30) aryloxy a carbonyloxy group, a carboxyl group, a nitro group or a hydroxyl group; or R?i to Rm may be bonded to an adjacent substituent via a (C3_C3〇)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form an alicyclic or monocyclic or polycyclic aromatic ring; To R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.

Ri至Ru係藉由下列結構例示，但不限於此。 HSC-| F-| H,^| h3C^0-| 0_| NC-0-| F-〇_| (—&丨&丨8·1 0^1扠丨OH汾丨Ri to Ru are exemplified by the following structures, but are not limited thereto. HSC-| F-| H,^| h3C^0-| 0_| NC-0-| F-〇_| (—&丨&丨8·1 0^1 fork丨OH汾丨

體例示，但不限於此。 94960 12 201113238The example is, but is not limited to. 94960 12 201113238

13 94960 £；' 20111323813 94960 £;' 201113238

本發明之有機電場發光化合物可如下列反應方案1所 示般製備。 反應方案1The organic electroluminescent compound of the present invention can be prepared as shown in the following Reaction Scheme 1. Reaction scheme 1

其中，匕至R"、X及Y係如化學式1所定義。 14 94960 201113238 本發明提供一種有機電場發光裝置，其包含第一電 極；第二電極；以及一層或多層插置於該第一電極與該第 二電極間之有機層，其中，該有機層包括一種或多種化學 式1所表示之有機電場發光化合物。該有機電場發光化合 物係作為電場發光層之主體材料。 此外，該有機層可包括電場發光層，該電場發光層除 了包括一種或多種化學式1所表示之有機電場發光化合物 之外，還可進一步包括一種或多種摻雜劑。對於施加至本 發明之有機電場發光裝置之摻雜劑沒有特別限制。 較佳地，用於本發明之有機電場發光裝置之摻雜劑選 自化學式2及化學式3 : 化學式2Among them, 匕 to R", X and Y are as defined in Chemical Formula 1. 14 94960 201113238 The present invention provides an organic electric field light-emitting device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises a Or a plurality of organic electroluminescent compounds represented by Chemical Formula 1. The organic electric field luminescent compound serves as a host material of the electric field luminescent layer. Further, the organic layer may include an electric field luminescent layer which may further include one or more dopants in addition to one or more organic electroluminescent compounds represented by Chemical Formula 1. There is no particular limitation on the dopant applied to the organic electric field light-emitting device of the present invention. Preferably, the dopant used in the organic electroluminescent device of the present invention is selected from Chemical Formula 2 and Chemical Formula 3: Chemical Formula 2

化學式3Chemical formula 3

其中，Arn及An2獨立表示具有或不具有取代基之 (C1--C30)烷基、具有或不具有取代基之（C6-C30)芳基、具 有或不具有取代基之（C4-C30)雜芳基、具有或不具有取代 基之（C6-C30)芳基胺基、（C1-C30)烷基胺基、具有或不具 有取代基之5員至7員雜環烷基、與一個或多個具有或不 具有取代基之芳香環稠合之5員至7員雜環烷基、具有或 15 94960 201113238 不具有取代基之（C3-C30)環烷基或與一個或多個具有或不 具有取代基之芳香環稠合之（C3-C30)環烷基，或者Arn與 Am可經由具有或不具有稠合環之（C3-C30)伸烷基或 (C3-C30)伸烯基相鍵聯以形成脂環、或單環或多環之芳香 環； 當c為1時，Αη3表示具有或不具有取代基之（C6-C30) 芳基、具有或不具有取代基之（C4-C30)雜芳基或選自下列 結構之取代基；Wherein, Arn and An2 independently represent (C1--C30)alkyl group having or without a substituent, (C6-C30) aryl group having or without a substituent, and having or not having a substituent (C4-C30) Heteroaryl, (C6-C30)arylamino group with or without a substituent, (C1-C30)alkylamino group, 5- to 7-membered heterocycloalkyl group with or without a substituent, and one Or a 5- to 7-membered heterocycloalkyl group fused with an aromatic ring having or without a substituent, having or having a substituent of (C3-C30) cycloalkyl or having one or more of 94 94960 201113238 Or an aromatic ring fused (C3-C30) cycloalkyl group having no substituent, or Arn and Am may be via (C3-C30) alkyl or (C3-C30) alkylene with or without a fused ring The base phase is bonded to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when c is 1, Αη3 represents a (C6-C30) aryl group with or without a substituent, with or without a substituent ( a C4-C30)heteroaryl group or a substituent selected from the following structures;

當c為2時，Αη3表示具有或不具有取代基之（C6-C30) 伸芳基、具有或不具有取代基之（C4-C30)伸雜芳基或選自 下列結構之取代基；When c is 2, Αη3 represents a (C6-C30) extended aryl group having a substituent or a (C4-C30) heteroaryl group having or not having a substituent or a substituent selected from the following structures;

Aru及Αη5表示具有或不具有取代基之（C6-C30)伸芳 基或具有或不具有取代基之（C4-C30)伸雜芳基； R201至R2G3獨立表示氫、氣、具有或不具有取代基之 (C1-C30)烷基或具有或不具有取代基之（C6-C30)芳基； d表示1至4之整數；以及 e表示整數0或1。 電場發光層可為單層，作為其中發光之層，或可為其 16 94960 201113238 中兩層或更多層層積之多層。於本發明之構型中，當主體-摻雜劑係呈混合物使用時，確定由本發明之電場發光主體 可獲得顯著提升的發光效率。其可以0. 5至10重量％之摻 雜濃度配置。與其他主體材料相比，本發明之電場發光主 體具有關於電洞及電子的優異傳導性以及優異之材料安定 性，藉此顯現顯著提高之壽命及改善之發光效率之特徵。 化學式3之摻雜劑化合物可藉由第10-2009-0023442 號韓國專利申請案所揭示之化合物例示之。更佳地，該等 摻雜劑化合物選自下列結構，但不限於此。Aru and Αη5 represent a (C6-C30) extended aryl group with or without a substituent or a (C4-C30) heteroaryl group with or without a substituent; R201 to R2G3 independently represent hydrogen, gas, with or without a (C1-C30)alkyl group of a substituent or a (C6-C30) aryl group having or without a substituent; d represents an integer of 1 to 4; and e represents an integer of 0 or 1. The electroluminescent layer may be a single layer, as a layer in which light is emitted, or may be a multilayer of two or more layers thereof in 16 94960 201113238. In the configuration of the present invention, when the host-dopant is used in a mixture, it is determined that a significantly improved luminous efficiency can be obtained by the electroluminescent body of the present invention. It may be disposed at a doping concentration of 0.5 to 10% by weight. Compared with other host materials, the electroluminescent body of the present invention has excellent conductivity with respect to holes and electrons and excellent material stability, thereby exhibiting characteristics of significantly improved life and improved luminous efficiency. The dopant compound of Chemical Formula 3 can be exemplified by the compound disclosed in Korean Patent Application No. 10-2009-0023442. More preferably, the dopant compounds are selected from the following structures, but are not limited thereto.

201113238201113238

於本發明之有機電子裝置中，該有機層除了包括化學 式1所表示之有機電場發光化合物，還可同時進一步包含 一種或多種選自芳基胺化合物及苯乙烯基芳基胺化合物所 18 94960 201113238 a 組成群組之化合物。§亥專方基胺化合物或苯乙稀基芳基胺 化合物係例示於第10-2008-0123276號、第 10-2008-0107606 號或第 10-2008-0118428 號韓國專利申 請案，但不限於此。 此外，於本發明之有機電場發光裝置中，該有機層除 了包括化學式1所表不之有機電場發光化合物之外，還可 進一步包括一種或多種選自下列所組成群組之金屬：第1 族之有機金屬、第2族、第4周期與第5周期過渡金屬、 鋼系金屬及d-過渡元素；或錯合物化合物。該有機層可包 括電場發光層及電荷產生層。 此外’該有機層除了包括化學式1所表示之有機電場 發光化合物之外，還可同時包括一層或多層發出藍光、綠 光及紅光之有機電場發光層以實現發出白光之有機電場發 光裝置。發出藍光、綠光或紅光之化合物係揭示於第 10-2008-0123276 號、第 10-2008-0107606 號或第 10-2008-0118428號韓國專利申請案中，但不限於此。 於本發明之有機電場發光裝置中，可將一層（後文中 稱為「表面層」）選自硫屬化合物（chalcogenide)層、金屬 鹵化物層及金屬氧化物層之層體設置於該電極對之一個或 二個電極的内表面上。更具體而言，可將矽與鋁之金屬硫 屬化合物（包括氧化物）層設置於該電場發光介質層之陽極 表面上，以及將金屬鹵化物層或金屬氧化物層設置於該電 場發光介質層之陰極表面上。藉此，可得到操作安定性。 硫屬化合物可為，例如Si0x(lSx$2)、 19 94960 201113238 A10x(lSx$l. 5)、SiON、SiAlON 等。金屬鹵化物可為， 例如LiF、MgF2、CaFz、稀土金屬之氟化物等。金屬氧化物 之貫例可為 Cs2〇、Li2〇、MgO、SrO、BaO、CaO 等。 於本發明之有機電場發光裝置中，亦較佳將電子傳輸 化合物與還原性摻雜劑之混合區域或電洞傳輸化合物與氧 化性換雜劑之混合區域設置於如是製造之電極對的至少一 表面上。這樣的話，由於電子傳輸化合物被還原成陰離子 因而使電子更㈣地自混合區域注入及傳輸至電場發光介 質。此外，由於電洞傳輸化合物被氧化而形成陽離子，因 此使電洞更輕易地自混合區蛣、'* & 匕 硃/主入及傳輸至電場發光介 質。較佳的氧化性摻雜劑包括各 物（acceptor c⑽pound)。較佳的、，易士&及接受體化合 屬、驗金屬化合物、驗土金屬、^性摻雜劑包括驗金 此外，具有兩層或更多層電場金屬及其展合物。 有稱為發出白光之情形）電場發光光層之白色（本文中 雜劑層用來作為電荷產生層^造可藉由將還原性摻 有利效果 合物具有良好發光效 柃製造具有非常良好操 由於本發明之有機電場發光化 率及優異的壽命特性，因此其可用 作哥命之0LED。 最佳模式 94960 20 201113238 以任何形式限制本發明之範圍。 [製備例1 ]化合物4之製備In the organic electronic device of the present invention, the organic layer may further comprise one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds, in addition to the organic electroluminescent compound represented by Chemical Formula 1. 18 94960 201113238 a Compounds that make up the group. The invention is exemplified in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 10-2008-0118428, but is not limited thereto. this. Further, in the organic electric field light-emitting device of the present invention, the organic layer may further include one or more metals selected from the group consisting of: in addition to the organic electroluminescent compound represented by Chemical Formula 1: The organometallic, Group 2, 4th and 5th cycle transition metals, steel based metals and d-transition elements; or complex compounds. The organic layer may include an electric field luminescent layer and a charge generating layer. Further, the organic layer may include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more layers of an organic electroluminescent layer emitting blue, green, and red light to realize an organic electric field emitting device that emits white light. A compound which emits blue light, green light or red light is disclosed in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 10-2008-0118428, but is not limited thereto. In the organic electric field light-emitting device of the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be provided on the electrode pair. On the inner surface of one or both of the electrodes. More specifically, a metal chalcogenide (including oxide) layer of bismuth and aluminum may be disposed on the anode surface of the electric field luminescent medium layer, and a metal halide layer or a metal oxide layer may be disposed on the electric field luminescent medium. On the cathode surface of the layer. Thereby, operational stability can be obtained. The chalcogen compound may be, for example, Si0x (lSx$2), 19 94960 201113238 A10x (lSx$1.5), SiON, SiAlON, or the like. The metal halide may be, for example, LiF, MgF2, CaFz, a fluoride of a rare earth metal, or the like. A specific example of the metal oxide may be Cs2〇, Li2〇, MgO, SrO, BaO, CaO or the like. In the organic electric field light-emitting device of the present invention, it is also preferred to provide a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant in at least one of the electrode pairs to be manufactured. On the surface. In this case, since the electron transporting compound is reduced to an anion, the electrons are more (4) injected and transported from the mixed region to the electric field illuminating medium. In addition, since the hole transporting compound is oxidized to form a cation, the hole is more easily self-mixed, ', '* & 匕 / 主 主 主 主 主 主 主 主 主 主 主 主 主 主 主 主 主 主 主 主 主 主Preferred oxidizing dopants include the individual (acceptor c (10) pound). Preferably, the Lewis & and the acceptor compound, the metal compound, the soil metal, the dopant include a gold test. In addition, there are two or more layers of electric field metal and its exhibit. There is a white light called an electric field illuminating light layer (referred to as the case where white light is emitted) (the impurity layer used herein as a charge generating layer can be manufactured by using a reductive doping advantageous effect compound with good luminescent effect. The organic electric field luminescence rate and excellent life characteristics of the present invention can be used as the OLED of the genius. The best mode 94960 20 201113238 limits the scope of the invention in any form. [Preparation Example 1] Preparation of Compound 4

化合物1-1之製備 將 6, 6, 12, 12-四乙基-6, 12-二氫茚并[1，2-b] S (10 公克（g)，27. 28 毫莫耳（mm〇i))及 A1C13(7. 27 g)添加至二 氣甲烷（MC)(500毫升（mL))之後，添加鄰笨二曱酸酐（6. 〇6 g，40.92 mmol)，於40°C回流攪拌該混合物12小時。緩 慢添加蒸餾水及鹽酸之後，以MC萃取產物並使用硫酸鎂去 除剩餘水分。乾燥’再經管柱分離而獲得化合物g， 23. 31 mmol, 85. 47%)。 化合物1-2之製備 將化合物1-1(12 g，23. 31 mmol)及乙酸（6〇 mL)添加 至硫酸（60 mL)之後’於12(TC回流攪拌該混合物8小時。 冷卻至室溫’添加蒸餾水並以NaOH水溶液中和，以MC萃 取產物並使用硫酸鎂去除剩餘水分。乾燥，再經管柱分離 而獲得化合物 1-2(3. 5 g，7.04 nrniol，30.23%)。 21 94960 201113238 化合物1-3之製備 將 2-溴萘（3. 94 g，19. 02 mmol)溶於 THFC100 mL)， 於-78°C 添加 n-buLi(7.8mL, 19.73mmol, 2.5M 於己烷 中）。1小時後，添加化合物1-2(3.5 g, 7.04 mmol)。緩 慢加熱該混合物，並於室溫回流攪拌12小時。添加蒸餾水 並以乙酸乙酯（EA)萃取之後，使用硫酸鎂去除剩餘水分。 乾燥’再經管柱分離而獲得呈混合物態之化合物1 - 3 (7 g )。 化合物4之製備 將化合物1-3(7 g，混合物）、碘化鉀（KI)(4. 4 g，26. 56 mmol)、NaH2P〇3H2〇(5.6 g，53. 12 mmol)及乙酸（60 mL)混 合並回流擾拌。12小時後，將混合物冷卻至室溫》添加蒸 餾水，於減壓下過濾所產生的固體並以NaOH水溶液洗膝該 固體，經由管柱分離獲得化合物4(3. 2 g，4. 45 mmol)。 [製備例2]化合物28之製備Preparation of Compound 1-1 6,6,12,12-tetraethyl-6,12-dihydroindeno[1,2-b] S (10 g (g), 27.28 mmol (mm) After 〇i)) and A1C13 (7. 27 g) were added to di-methane (MC) (500 ml (mL)), o-paraic acid anhydride (6. 〇6 g, 40.92 mmol) was added at 40 ° C. The mixture was stirred at reflux for 12 hours. After slowly adding distilled water and hydrochloric acid, the product was extracted with MC and magnesium sulfate was used to remove residual water. Drying was followed by column separation to give compound g, 23. 31 mmol, 85.47%. Preparation of Compound 1-2 After adding compound 1-1 (12 g, 23.31 mmol) and acetic acid (6 mL) to sulfuric acid (60 mL), the mixture was stirred at reflux for 8 hours at TC. Cooling to room Distilled water was added and neutralized with aqueous NaOH, and the product was extracted with MC and the residual water was removed using magnesium sulfate, dried, and then separated by column to obtain compound 1-2 (3.5 g, 7.04 nrniol, 30.23%). 201113238 Preparation of compound 1-3 2-bromonaphthalene (3.94 g, 19.2 mmol) was dissolved in THF (100 mL), n-buLi (7.8 mL, 19.73 mmol, 2.5 M in hexanes) in). After 1 hour, compound 1-2 (3.5 g, 7.04 mmol) was added. The mixture was slowly heated and stirred under reflux at room temperature for 12 hours. After adding distilled water and extracting with ethyl acetate (EA), residual water was removed using magnesium sulfate. Drying was further separated by a column to obtain Compound 1 - 3 (7 g) in a mixture. Preparation of Compound 4 Compound 1-3 (7 g, mixture), potassium iodide (KI) (4.4 g, 26.56 mmol), NaH2P〇3H2 (5.6 g, 53.12 mmol) and acetic acid (60 mL) Mix and reflux to disturb. After 12 hours, the mixture was cooled to room temperature. Distilled water was added, the resulting solid was filtered under reduced pressure and the solid was washed with NaOH aqueous solution, and the compound 4 was obtained by column separation (3.2 g, 4.45 mmol) . [Preparation Example 2] Preparation of Compound 28

94960 201113238 « 化合物2-1之製備 將 2-溴-9, 9-二甲基第（20 g，73. 21 mmol)、A1C13 (19. 5 g, 146. 4 mmol)及 MC(500 mL)混合，添加化合物 A 並於40°C回流攪拌。12小時後，添加蒸餾水及1M HC1水 溶液。以MC萃取、於減壓下蒸餾後進行管柱分離而獲得化 合物 2-1(30 g，71.21 mmol, 97.21%)。 化合物2-2之製備 將化合物 2-1(30 g，71. 21 mmol)、硫酸（100 mL)及 乙酸（100 mL)混合並於120°C回流攪拌。10小時後，將混 合物冷卻至室溫並添加蒸餾水。於減壓下過濾所產生的固 體後，以曱醇及EA再結晶而獲得化合物2-2(4 g，9. 91 mmol, 13. 95%)。 化合物2-3之製備 將化合物2-2(4. 2 g, 10. 37 mmol)、2-硝基苯硼酸（2 g，12· 49 mmol)、Pd(PPh3)4(0. 59 g, 0. 51 mmol)、3M K2CO3 水溶液（10 mL)、甲苯（70 mL)及乙醇（30 mL)混合並回流攪 拌。12小時後，將化合物冷卻至室溫。添加蒸餾水並以EA 萃取之後，使用硫酸鎂去除剩餘水分。乾燥，再經管柱分 離而獲得化合物 2-3(3. 7 g, 8.30 mmol，80.05%)。 化合物2-4之製備 將化合物2-3(3. 7 g，8. 30 mmol)與三乙基膦（50 mL) 混合並於回流下攪拌該混合物。10小時後將該混合物冷卻 至室溫。蒸餾，再經管柱分離而獲得化合物2-4(2, 5 g, 6. 04 mmol, 72.84%)。 23 94960 201113238 化合物2-5之製備 將化合物 2-4(2. 5 g，6. 04 mmol)、碘苯（2.46 g，12. 〇9 mmol)、CuI(1.72g，9.06mmol)、K2C03(2.50 g，18. 13mmol) 及1，2-二氣苯（50 mL)混合並於19(TC加熱。24小時後， 將混合物冷卻至室溫並於減壓下蒸餾有機溶劑。添加蒸餾 水並以EA萃取後，於減壓下蒸餾，再經管柱分離而獲得化 合物 2-5(2. 7 g，5.51 mmol, 91.31%)。 化合物2-6之製備 以製備化合物卜3之相同方法藉由於製備例i中使用 化合物2-5而獲得化合物2-6。 化合物28之製備 1中使用化 53%)。 以製備化合物4之相同方法藉由於製備例 合物2-6而獲得化合物28(2. 1 g 9 cm »5 mmol, [製備例3]化合物30之製備94960 201113238 « Preparation of compound 2-1 2-bromo-9,9-dimethyl (20 g, 73.21 mmol), A1C13 (19.5 g, 144.6 mmol) and MC (500 mL) After mixing, Compound A was added and stirred under reflux at 40 °C. After 12 hours, distilled water and 1 M HCl aqueous solution were added. The mixture was extracted with MC, distilled under reduced pressure, and then subjected to column separation to obtain Compound 2-1 (30 g, 71.21 mmol, 97.21%). Preparation of Compound 2-2 Compound 2-1 (30 g, 71.21 mmol), sulfuric acid (100 mL), and acetic acid (100 mL) were mixed and stirred under reflux at 120 °C. After 10 hours, the mixture was cooled to room temperature and distilled water was added. After the resulting solid was filtered under reduced pressure, compound 2-2 (4 g, 9.91 mmol, 13. 95%) was obtained by recrystallization from methanol and EA. Preparation of compound 2-3 Compound 2-2 (4.2 g, 10.37 mmol), 2-nitrophenylboronic acid (2 g, 12.49 mmol), Pd(PPh3)4 (0. 59 g, 0. 51 mmol), 3M K2CO3 aqueous solution (10 mL), toluene (70 mL) and ethanol (30 mL). After 12 hours, the compound was cooled to room temperature. After adding distilled water and extracting with EA, magnesium sulfate was used to remove residual water. Drying, and separation by column to give compound 2-3 (3.7 g, 8.30 mmol, 80.05%). Preparation of Compound 2-4 Compound 2-3 (3.7 g, 8.30 mmol) was mixed with triethylphosphine (50 mL) and the mixture was stirred under reflux. After 10 hours, the mixture was cooled to room temperature. Distillation and separation by column to give compound 2-4 (2, 5 g, 6.04 mmol, 72.84%). 23 94960 201113238 Preparation of compound 2-5 Compound 2-4 (2.5 g, 6.04 mmol), iodobenzene (2.46 g, 12. 〇9 mmol), CuI (1.72 g, 9.06 mmol), K2C03 ( 2.50 g, 18.13 mmol) and 1,2-dibenzene (50 mL) were mixed and heated at 19 (TC). After 24 hours, the mixture was cooled to room temperature and the organic solvent was distilled under reduced pressure. After extraction with EA, it was distilled under reduced pressure, and then separated by column to give compound 2-5 (2.7 g, 5.51 mmol, 91.31%). Preparation of compound 2-6 was prepared by the same method as in the preparation of compound 3 Compound 2-6 was used in Example i to give compound 2-6. Compound 28 was used in Preparation 1 (53%). In the same manner as in the preparation of the compound 4, Compound 28 was obtained by the preparation of the compound 2-6 (2. 1 g 9 cm of 5 mmol, Preparation of Compound 30 of [Preparation Example 3]

94960 201113238 化合物3-1之製備 將 1，4-二曱基-2, 5-二溴苯（10 g，37. 88 mmol)、2-(曱 氧基羰基）苯硼酸（17 g, 94. 71 mmol)、Pd(PPh〇4(2. 18 g， 1· 89 mmol)、2M K2CO3 水溶液（60 mL)、曱苯（200 mL)及乙 醇（100 mL)混合並回流攪拌。6小時後，將化合物冷卻至 室溫。添加蒸餾水並以EA萃取之後，使用硫酸鎂去除剩餘 水分。乾燥，再經管柱分離而獲得化合物3-1(11 g，29. 37 mmol, 77. 55%)。 化合物3-2之製備 將化合物 3-1(11 g，29.37 mmol)溶於 THF(400 mL) 並缓慢添加甲基溴化鎂（48.96 mL，146.88 mmol, 3.0M於 二乙醚中）。於60°C回流攪拌該混合物12小時並冷卻至室 溫。緩慢添加蒸餾水並以EA萃取之後，使用硫酸鎂去除剩 餘水分。乾燥，再經管柱分離而獲得化合物3-2(9 g，24. 03 mmol， 81.82%)。 化合物3-3之製備 將化合物3-2(9 g，24. 03 mmol)與乙酸（100 mL)及 H3P〇4(100 mL)混合並於120°C加熱該混合物。10小時後， 將混合物冷卻至室溫並添加蒸餾水。於減壓下過濾所產生 的固體並以NaOH水溶液及甲醇洗滌而獲得化合物3-3(6 g， 17· 72 mmol, 73. 76%)。 化合物3-4之製備 以製備化合物1-1之相同方法藉由於製備例1中使用 化合物3-3而獲得化合物3-4(6.3叾，12.95 111111〇1，73.1°/0)。 25 94960 201113238 化合物3-5之製備· 以製備化合物1-2之相同方法藉由於製備例1中使用 化合物 3-4 而獲得化合物 3-5(4. 3 g，9. 18 mmol, 70. 1%)。 化合物3-6之製備 以製備化合物1-3之相同方法藉由於製備例1中使用 化合物3-5而獲得化合物3-6。 化合物30之製備 以製備化合物4之相同方法藉由於製備例1中使用化 合物3-6而獲得化合物30(2 3 g，3 33顏〇1，37%)。 以製備例1之相同製程製備有機電場發光化合物1至 35 ’表1為所製備電場發光化合物之ιΗ腿1?及MS/FAB數 據。 表1 化合物 NMR(CDC13, 200 MHz) M 5/FAB 1 ^)Γ 7：35*7H38!k 1^ΓίΓ_2.64(6Η,. 7.76{1H, s), 7 77(1M f .7·^5<1Η» » 8.07(1H, s), (h, ) S), 7-87<lH, m), δ = 1.48(18H,~~ϋ ---- m), 7.35~7 38(3l/ 6 , S>, 1,78<6H, s) 7 8.07 (1H, s), (H, ) f 7-87UH, m), s), 7.28(1H, 7.69(1H, s), 7·98(2Η, in), 438.60 其伹 438.23 2 s), 7.28(1H, 7.69(1H, s), 7.98(2H, m), 522.76 522.33 3 δ 〇·9 (12h, m), 1 91(Rh «、 7.38-7.41(5«, m), V.51：7 55 (9H 7.76(1H, s), 7 77ΠΗ \ ·,5(9Η» » s), (H, ) 7-77<^ s)f 7.87~7.91(3H, 7.28(1H, m), 7-69(lH, s), ml , 8.07(1H, 618.85 618.33 4 7.38-7.39 (3H, m), ； 7 m)； 7.73(2H, m), 7.76(1H> s) 7 m，； n〇, 8(4H, m), 8.07(1H. ](1 ’ S)r 7.28(1H, m), 7.69(1H, s), 7.87~7.92(5H, 718.96 718.36 26 94960 201113238 5 δ = 0.9(12Η, m) , 1·91(8Η, πι) , 2.34 (2Η, s), 7.28 〜7·39(12Η, m), 7·55(1Η, π〇, ·7.69(1Η, s), 7·76(1Η, S), 7.77(1Η, s), 7.87-7.9K3H, m) r 8.07(1Η, s) , (Η,) 646.90 646.36 6 δ = 0.9(12Η, m) , 1.91(8Η, πι) , 2.34 (12Η, s), 7.28〜7_31(3Η, m), 7.38〜7·39(3Η, m), 7.55〜7·6(5Η, m), 7.69(1H, s), 7·76(1Η, s), 7·77(1Η, s), 7.87〜7.91(3H, m), 8.07(1H, s), (H,) 674.95 674.39 7 δ = 0.9C12H, m), 1.91 (8H, m) , 7.28(1H, m), 7.38-7.39(3H, m) , m), 7.69(1H, s), 7.76(1H, s), 7.77(1H, s), 7.82-7.9K11H, m) f 8.07(1H, s), (H,) 668.87 668.32 θ δ - 0.9(12H, m) , 1.9K8H, m), 7 · 28 〜7 · 3 (5H, m) r 7.38-7.39(7H, m) , 7.55(1H, m) f 7.69(1H, s) , 7.76(1H, s), 7.77(1H, s), 7.87-7.9K3H, m), 8.07(1H, s) f (H,) 654.83 654.31 9 δ - 0.25(18H, s), 0.9(12H, in), 1.91(8H, m) , 7.28(1H, m), 7.38~7.39(3H, m) , 7.46(4H, m), 7.55(1H, m), 7.69(1H, s), 7.76(1H, s), 7.77(5H, s), 7.77(0H, m), 7·87〜7,91(3H, m), 8·07(1Η, s), (H,) 763.21 762.41 10 δ = 0.9{12Hf m), 1.6(4H/ m) f 1.91(12H, m) f 2.85(4H, m), 4.13(2H, m) , 6·92(8Η, m), 7.28(1H, m), 7.35-7.38{3H, m) , 7.55(1H, m), 7.69(1H, s) , 7.76(1¾. s), 7.77(1H, s), 7.87(1H, m) , 7.98{2H, m) , 8.07(1H, s), (H,) 727.03 726.42 ：L1 δ = 0.9(12H, m) , X.72(8H, m), 1.9K8H, m) , 2.74(8H, m)r 6.88(2H/ m) f 6.98{2H, m), 7.15(2Hf m) , 7.28(1H, m) r 7.38-7.39(3H, m) , 7.55(1H, m) , 7.69(1H, s), 7.76(lHf s)t 7.77(1H, s)( 7.87~7.91(3H, m) , 8.07(XH, S), (H,) 727.03 726.42 12 δ = 0.9(12H, m) , 1.71 (8Hf m), 1.9K8H, m), 2·01〜2.02(22H, m), 7.28(1H, m), 7.35^7.38(3H, m), 7.55(1H, m), 7.69(1H, s), 7.76(1H, s), 7.77(1H, s), 7·8*7(1Η, m), 7.98(2H, m), 8.07(1H, s), (H,) 735.09 734.49 13 δ = 0.9(12H, m), 1.9K8H, m) , 6.63(8H, m) , 6.81(4Hf m), 7.2(8H, m), 7_28(1H, m) , 7.38〜7·39(3H, m), 7.55(1H, m), 7.69(2H, s), 7.77(1H, s), 7.87-7.91(3Hf m), 8(1H, s)r (H,) 801.07 800.41 14 δ « 0.9(12H, m), 1.91{8H, m) , 2.34(36H, s), 6.91(8H, m), 7.28(1H, m) , 7_38〜7·39(3H, m) , 7.55(1H, m), 7.69(1H, s), 7.76(1H, s) , 7.77(1H, s), 7.79-7.81(8H, m), 7.87-7.91(3H, m), 8.07{1H, s)f {H,) 1115.19 1114.68 1!5 δ 0.9(12H, m), 1.91(8H, m) , 7.28(1H, m), 7.35-7.39(5H, in) , 7.55-7.6(3H, m) , . 7.69(1H, s), 7.76{1H, s), 7.77(1H, s) r 7.78(2H, m) , 7.87-7.91(3H, m), 7.98{2H, πι) , 8.06(2H, m) # 8.07(1H, s) , 8.1(2H, m) 720.94 720.35 1朽 δ = 0,9(12H, m) , 1.91(8H, m), 7.25^7.28(9H, m), 7.38〜7.41(5H, m) , 7.51-7.55(9H, m), 7.69(1H, s), 7.76{1H, s), 7.77(1H, s), 7.87-7.91{3H, m), 8.07(1H, s), (Hf ) 771.04 770.39 17 δ - 0.9(12H, m) , 1.91(8H, m), 7.19-7.28(7H, m), 7.38-7.41(7H, m), 7.55(1H, m) , 7.69(1H, s), 7.76(1H, s), 7.77(1H# s)r 7.87-7.9K3H, m) , 8.07{1H, s), (H,) 682.98 682.27 27 94960 201113238 18 δ = 0.9(12Η, m), 1·91(8Η, m), 7.25-7.39{7Η, m), 7.45-7.63(14Η, m) , 7.69(2Η, s), 7.69(0Η, m), 7.76(1Η, s) , 7.77(2Η, s), 7.77(OH, m), 7.87-7.94(5Hr m), 8·07(1Η, s), 8.1~8.12(2Η, m), 8·49(1Η, m), 8.55{1Η, m) 949.23 948.44 19 δ = 0.9(12Η, m), 1.9K8H, m) f 6.63{6Η, in), 6.8K4H, m), 6.89(2H, m), 6.99-7.05(8H, m), 7.2-7.31(9H, m), 7.38-7.39(3Η, m), 7.55(1H/ m), 7.69(1H, s), 7.76(1H, s), 7.77(1H, s), 7.87-7.9K3H, m) , 8.07{1H; s), (H,) 1001.30 1000.48 20 δ = 0·9(12Η, m), 1.91(8H, m), 7.25-7.28(2H, m), 7.38*7.55(14H, m), 7.69(1H, s), 7.72*7.75(2H, m), 7.76(1H, s), 7.77(5H, s), 7.77(0H, m), 7.83-7.95(10H, m), 8.07(1H, s), (H,) 1015.16 1014.38 21 δ = 0.9(12H, m), 1.91{8H, m), 7.25-7.4(10Hr m), 7.5-7.55(3H, m) , 7;63(2H, m), 7.69(1H, s), 7.77(1H, s), 7.8(1H, s), 7.87-7.94(5H, m), 8.1(1H, s), 8.12(2H, m), 8.55(2H, m) 797.04 796.38 22 δ = 0·9(12Η, m), 1.91-1.96(X2H, m), 2.76 (4H, m), 3.06(4H, m), 6.55(2H, m), 6.72{2H, m) , 7.05-7.07{4H, m) , 7.28(1H, ml, 7.38-7.39(3H, m) , 7.55(1H, m), 7.69(2H, s), 7.77(1H, s), 7.87-7.91(3H, m), 8(1H, s), (H,) 729.00 728.41 23 δ « 0.9(12H/ m), 1.91{8H, m) , 7·28(1Η, m), 7·38〜7·41(4H, m), 7.51-7.59(8H, m) r 7.69(1H, s), 7.73(lHf m), 7.76(1H, s), 7.77(1H, s), 7.87-7.92(4H, m), 8(2H, m), 8.07(1H, s), (H,) 668.91 668.34 24 δ = 0.9(12H, m) f 1·72(6Η, s), 1-91 (8H, m), 7.25-7.28(6H, m), 7.38-7.41(5Hf m) , 7.51-7.55(6H, m), 7·63(1Η, m), 7_69(1H, s), 7_76(1H, s), 7.77(2H, s), 7.77{0H, m), 7.87-7.93(5H, m), 8.07I1H, s)f (H,) 811.10 810.42 25 δ ·= 0.9(12H, m), 1.91(8H, m), 7.28(1H, m), 7.38〜7.41(2H, m), 7.51〜7·61(12H, m), 7.69(1H, s), 7.73(2H, m), 7.76(1H, s), 7.77(1H, s), 7.87-8(8H, m), 8.07(1H, s), 8.13(1H, m> 795.06 794.39 26 δ = 0.9(12H, m), 1.91(8H, m), 7.28(1H, m), 7.38(1H, m), 7.55-7.6K11H, m) , 7.69(1H, s), 7·73(3Η, m), 7.76(1H, s), 7.77(1H, s), 7·87〜8(11H, m), 8·07(1Η, s), 8.13(1H, m) 845.12 844.41 27 δ = 0.9(12H, m), 1.72(6H, s), 1.91(8H, m), 7·28(2Η, m), 7.38{2H, in), 7.55-7.63 (10H, m), 7·69(1Η, s), 7.73(2H, m), 7.76(1H, s), 7.77(2H, s) , 7.77(0H, m), 7.87-8(10H, m), 8.07(1H, s)f 8.13(1H, m) 911.22 910.45 28 δ = 1_78(6H, s), 7.29(1H, m) , 7.39(2H, m), 7.45-7.5(4H, m), 7.54 (1H, s) , 7.58-7.63(9H, m), 7.73(2Hf m)/ 7.76(lHr s) f 7.91-7.92(4H, m) , 8(4H, m), 8.07(1H, s), 8.12I1H, m) , 8.85(1H, s), (H,) 711.89 711.29 29 δ = 1.78(6H, s), 7.29(1H, m), 7_41~7.52(9H, m), 7.54(1H, s), 7.58-7.63(10H, ra), 7.73<2H, m), 7.76(1H, s), 7.92~8(7H, m), 8.07(1H, s), 8.12-8.13(2H, m), 8.85(1H, s), (H,). 787.98 787.32 30 δ = 1.72(6H, s), 1.78(6H, s), 2.69(6H, s), 7.28(1H, m), 7.38~7.39(3H, m), 7.55~7.59(7H, m) , 7.73(2H, m), 7.76(1H, s), 7.87~7.92(5H, ra), 8(4H, in), 8.07(1H, s), 690.91 690.33 28 94960 201113238 (Η, , ------ 31 丨一一 s>, νϋΠ’θ 以’丄、·78，’ 2.45(3H，s>，2.69(6Η, 7 7~7 7·38(1Ηί 7.55~7.59(7Η, ιη), π·)'，8：〇7ίΐΗ： ：!： ,7η·76,(1Η，Sh 7·85~7·92(4Η, m)/ 6(4Η, 704.94 704.34 32 7 38-7 . S)； 7.28<1Η, m), 7 76 (Ϊη if' 7 〇7；55~7·59(7Η- 7·73(2Η, m), (H^s),7,87~7.92{5H,m),8(4H,ir〇,8.07(lH,S), 698.84 698.28 33 m)T 772|5(ϊΐΗ Π>>ό7·3?( = ο, m)' ?·4(1Η« 7.45~7.5(7Η, 7.91 UH 5ifH/*7 οι \ 7·58"*7-^3(11Η, m), 7·73(2Η, m), • / S), 7.91-7.92(2Η, m), 8(4Η/ m), 8.12(1Η, m) 760.92 760.29 34 1 7.58~7 63<9Η、、，如，7·45、7.5(悦 m), s) 7 7·73(2Η^ «Ο» 7.78(1Η, s), 7.86(1Η, „) . 14Ά, S), 7·91~7·92(2Η, m), 8(4Η, m), 8.12(1Η, r -------- 701.87 701.22 35 11 7 /〇!t>H， S), 7.32-v7.39(4H, m), 7.42(1H, s)" 7 7，fi,f2， 7·58~7·59(6Η» m), 7.66(1H, m), 7.73(2H， !),' (H ) 1H，S>，7·89~7·92(5η^ m)/ 8(4H, m), 8.07(1«! 636.78 636.25 [實施例1]使用本發明之有機電場發光化合物之〇LED裝 置之製造 使用本發明之有機電場發光化合物製造〇LED裝置。 首先使用超音波依序以二氯乙稀、丙綱、乙醇及蒸 餾水清洗由0LED用玻璃（Samsung Corning製造）所得之透 明電極ΙΤ0薄膜（15Ω/Ι：])，並儲存於異丙醇中備用。 然後，將ΙΤ0基板裝配於真空氣相沈積裒置之基板失 中。將4,4,，4” -參（N，N-(2-萘基）-苯基胺基）三苯"胺 (2-TNATA)置於該真空氣相沈積裝置之一小室中，接著將該 腔室通風達ΙΟ—托（t〇rr)真空。對該小室施加電流以= 2-TNATA，從而在該IT0基板上形成厚度為6〇奈米（咖')2 小室中，對， 接著，將Ν，Ν’ -雙U-萘基）-Ν，Ν’ -胺（ΝΡΒ)置於該真空氣相沈積裝置之另 94960 29 201113238 室施加電”11·以⑨發NPB，從而於該電洞注人層上形成厚度 為20 nm之電洞傳輸層。 又 形成電場發光層。 小室中作為主體， 形成電/同'主入層及電洞傳輸層之後，於電洞傳輸層上 。將化合物4置於真空氣相沈積裝置之一 ’並將化合物Ε置於另一小室中作爲摻雜 劑。以不同速度蒸發該兩種材料，從而以2至5重量％(以 主體材料為基準計）於電洞傳輸層上氣相沈積厚度為30 nm 之電場發光層。94960 201113238 Preparation of compound 3-1 1,4-didecyl-2,5-dibromobenzene (10 g, 37.88 mmol), 2-(decyloxycarbonyl)benzeneboronic acid (17 g, 94. 71 mmol), Pd (PPh〇4 (2. 18 g, 1.89 mmol), 2M K2CO3 aqueous solution (60 mL), benzene (200 mL) and ethanol (100 mL) were mixed and stirred under reflux. After 6 hours, The compound was cooled to room temperature. After adding distilled water and extracting with EA, the residual water was removed using magnesium sulfate, dried, and then separated by column to give compound 3-1 (11 g, 29.37 mmol, 77. 55%). Preparation of 3-2 Compound 3-1 (11 g, 29.37 mmol) was dissolved in THF (400 mL) and methyl magnesium bromide (48.96 mL, 146.88 mmol, 3.0 M in diethyl ether) was added slowly. C. The mixture was stirred under reflux for 12 hours and cooled to room temperature. After adding distilled water and extracting with EA, the residual water was removed using magnesium sulfate, dried, and then separated by column to obtain compound 3-2 (9 g, 24.03 mmol, 81.82%) Preparation of Compound 3-3 Compound 3-2 (9 g, 24.03 mmol) was mixed with acetic acid (100 mL) and H3P 〇4 (100 mL) and the mixture was heated at 120 ° C. After the time, the mixture was cooled to room temperature and distilled water was added, and the resulting solid was filtered under reduced pressure and washed with aqueous NaOH and methanol to give compound 3-3 (6 g, 17.72 mmol, 73.76%). Preparation of Compound 3-4 In the same manner as in the preparation of Compound 1-1, Compound 3-4 (6.3 叾, 12.95 111111 〇 1, 73.1 ° / 0) was obtained by using Compound 3-3 in Preparation Example 1. 25 94960 201113238 Preparation of Compound 3-5. In the same manner as in the preparation of Compound 1-2, Compound 3-5 (4.3 g, 9.18 mmol, 70.1%) was obtained by using Compound 3-4 in Preparation Example 1. Preparation of Compound 3-6 In the same manner as in the preparation of Compound 1-3, Compound 3-6 was obtained by using Compound 3-5 in Preparation Example 1. Preparation of Compound 30 was carried out in the same manner as in the preparation of Compound 4 in Preparation Example 1. Compound 30 was obtained using Compound 3-6 (2 3 g, 3 33 〇1, 37%). The organic electroluminescent compound 1 to 35 was prepared in the same manner as in Preparation Example 1. Table 1 is the SiO of the prepared electroluminescent compound. Leg 1? and MS/FAB data. Table 1 Compound NMR (CDC13, 200 MHz) M 5/FAB 1 ^) Γ 7:35*7H38!k 1^ΓίΓ_2.64(6Η,. 7.76{1H, s), 7 77(1M f .7·^5<1Η» » 8.07(1H, s), (h, ) S), 7-87<lH, m), δ = 1.48(18H,~~ϋ- m), 7.35~7 38(3l/ 6 , S>, 1,78<6H, s) 7 8.07 (1H, s), (H, f 7-87UH, m), s), 7.28 (1H, 7.69(1H, s), 7·98(2Η, in), 438.60 伹 438.23 2 s), 7.28(1H, 7.69(1H, s) , 7.98(2H, m), 522.76 522.33 3 δ 〇·9 (12h, m), 1 91 (Rh «, 7.38-7.41(5«, m), V.51:7 55 (9H 7.76(1H, s ), 7 77ΠΗ \ ·,5(9Η» » s), (H, ) 7-77<^ s)f 7.87~7.91(3H, 7.28(1H, m), 7-69(lH, s), ml , 8.07(1H, 618.85 618.33 4 7.38-7.39 (3H, m), ; 7 m); 7.73(2H, m), 7.76(1H> s) 7 m,; n〇, 8(4H, m), 8.07 (1H. ](1 ' S)r 7.28(1H, m), 7.69(1H, s), 7.87~7.92(5H, 718.96 718.36 26 94960 201113238 5 δ = 0.9(12Η, m) , 1·91(8Η , πι) , 2.34 (2Η, s), 7.28 〜7·39(12Η, m), 7·55(1Η, π〇, ·7.69(1Η, s), 7·76(1Η, S), 7.77( 1Η, s), 7.87-7.9K3H, m) r 8.07(1Η, s) , (Η,) 646.90 646.36 6 δ = 0.9(12Η, m) , 1.91(8Η, πι) , 2.34 (12Η, s), 7.28~7_31(3Η, m), 7.38~7·39 (3Η, m), 7.55~7·6(5Η, m), 7.69(1H, s), 7·76(1Η, s), 7·77(1Η, s), 7.87~7.91(3H, m), 8.07( 1H, s), (H,) 674.95 674.39 7 δ = 0.9C12H, m), 1.91 (8H, m), 7.28(1H, m), 7.38-7.39(3H, m) , m), 7.69(1H, s), 7.76(1H, s), 7.77(1H, s), 7.82-7.9K11H, m) f 8.07(1H, s), (H,) 668.87 668.32 θ δ - 0.9(12H, m) , 1.9K8H , m), 7 · 28 〜7 · 3 (5H, m) r 7.38-7.39(7H, m) , 7.55(1H, m) f 7.69(1H, s) , 7.76(1H, s), 7.77(1H , s), 7.87-7.9K3H, m), 8.07(1H, s) f (H,) 654.83 654.31 9 δ - 0.25(18H, s), 0.9(12H, in), 1.91(8H, m) , 7.28 (1H, m), 7.38~7.39(3H, m), 7.46(4H, m), 7.55(1H, m), 7.69(1H, s), 7.76(1H, s), 7.77(5H, s), 7.77(0H, m), 7·87~7,91(3H, m), 8·07(1Η, s), (H,) 763.21 762.41 10 δ = 0.9{12Hf m), 1.6(4H/ m) f 1.91(12H, m) f 2.85(4H, m), 4.13(2H, m) , 6.92(8Η, m), 7.28(1H, m), 7.35-7.38{3H, m) , 7.55(1H , m), 7.69(1H, s), 7.76(13⁄4. s), 7.77(1H, s), 7.87(1H, m) , 7.98{2H, m) , 8.07(1H, s), (H,) 727.03 726.42 : L1 δ = 0.9(12H, m) , X.72(8H, m), 1.9K8H, m) , 2.74(8H, m)r 6.88(2H/ m) f 6.98{2H, m), 7.15(2Hf m) , 7.28(1H, m) r 7.38-7.39(3H, m) , 7.55(1H, m) , 7.69(1H, s), 7.76(lHf s)t 7.77 (1H, s) ( 7.87~7.91(3H, m) , 8.07(XH, S), (H,) 727.03 726.42 12 δ = 0.9(12H, m) , 1.71 (8Hf m), 1.9K8H, m), 2·01~2.02(22H, m), 7.28(1H, m), 7.35^7.38(3H, m), 7.55(1H, m), 7.69(1H, s), 7.76(1H, s), 7.77( 1H, s), 7·8*7(1Η, m), 7.98(2H, m), 8.07(1H, s), (H,) 735.09 734.49 13 δ = 0.9(12H, m), 1.9K8H, m ), 6.63(8H, m), 6.81(4Hf m), 7.2(8H, m), 7_28(1H, m) , 7.38~7·39(3H, m), 7.55(1H, m), 7.69(2H , s), 7.77(1H, s), 7.87-7.91(3Hf m), 8(1H, s)r (H,) 801.07 800.41 14 δ « 0.9(12H, m), 1.91{8H, m) , 2.34 (36H, s), 6.91(8H, m), 7.28(1H, m) , 7_38~7·39(3H, m) , 7.55(1H, m), 7.69(1H, s), 7.76(1H, s ), 7.77(1H, s), 7.79-7.81(8H, m), 7.87-7.91(3H, m), 8.07{1H, s)f {H,) 1115.19 1114.68 1!5 δ 0.9(12H, m) , 1.91(8H, m) , 7.28(1H, m), 7.35-7.39(5H, in) , 7.55-7.6(3H, m) , . 7.69(1H, s), 7.76{1H, s), 7.77( 1H, s) r 7.78(2H, m) , 7.87-7.91(3H, m), 7.98{2H, πι) , 8.06(2H, m) # 8.07(1H, s) , 8.1(2H, m) 720.94 720.35 1 decay δ = 0,9(12H, m) , 1.91(8H, m), 7.25^7.28(9H, m), 7.38~7.41(5H, m) , 7.51-7.55 (9H, m), 7.69(1H, s), 7.76{1H, s), 7.77(1H, s), 7.87-7.91{3H, m), 8.07(1H, s), (Hf ) 771.04 770.39 17 δ - 0.9(12H, m) , 1.91(8H, m), 7.19-7.28(7H, m), 7.38-7.41(7H, m), 7.55(1H, m) , 7.69(1H, s), 7.76(1H , s), 7.77(1H# s)r 7.87-7.9K3H, m) , 8.07{1H, s), (H,) 682.98 682.27 27 94960 201113238 18 δ = 0.9(12Η, m), 1·91(8Η , m), 7.25-7.39{7Η, m), 7.45-7.63(14Η, m), 7.69(2Η, s), 7.69(0Η, m), 7.76(1Η, s) , 7.77(2Η, s), 7.77(OH, m), 7.87-7.94(5Hr m), 8·07(1Η, s), 8.1~8.12(2Η, m), 8·49(1Η, m), 8.55{1Η, m) 949.23 948.44 19 δ = 0.9(12Η, m), 1.9K8H, m) f 6.63{6Η, in), 6.8K4H, m), 6.89(2H, m), 6.99-7.05(8H, m), 7.2-7.31(9H , m), 7.38-7.39(3Η, m), 7.55(1H/m), 7.69(1H, s), 7.76(1H, s), 7.77(1H, s), 7.87-7.9K3H, m) , 8.07 {1H; s), (H,) 1001.30 1000.48 20 δ = 0·9(12Η, m), 1.91(8H, m), 7.25-7.28(2H, m), 7.38*7.55(14H, m), 7.69 (1H, s), 7.72*7.75(2H, m), 7.76(1H, s), 7. 77(5H, s), 7.77(0H, m), 7.83-7.95(10H, m), 8.07(1H, s), (H,) 1015.16 1014.38 21 δ = 0.9(12H, m), 1.91{8H, m), 7.25-7.4(10Hr m), 7.5-7.55(3H, m), 7;63(2H, m), 7.69(1H, s), 7.77(1H, s), 7.8(1H, s), 7.87-7.94(5H, m), 8.1(1H, s), 8.12(2H, m), 8.55(2H, m) 797.04 796.38 22 δ = 0·9(12Η, m), 1.91-1.96(X2H, m ), 2.76 (4H, m), 3.06 (4H, m), 6.55 (2H, m), 6.72{2H, m), 7.05-7.07{4H, m), 7.28 (1H, ml, 7.38-7.39 (3H) , m) , 7.55(1H, m), 7.69(2H, s), 7.77(1H, s), 7.87-7.91(3H, m), 8(1H, s), (H,) 729.00 728.41 23 δ « 0.9(12H/ m), 1.91{8H, m) , 7·28(1Η, m), 7·38~7·41(4H, m), 7.51-7.59(8H, m) r 7.69(1H, s ), 7.73(lHf m), 7.76(1H, s), 7.77(1H, s), 7.87-7.92(4H, m), 8(2H, m), 8.07(1H, s), (H,) 668.91 668.34 24 δ = 0.9(12H, m) f 1·72(6Η, s), 1-91 (8H, m), 7.25-7.28(6H, m), 7.38-7.41(5Hf m) , 7.51-7.55( 6H, m), 7·63(1Η, m), 7_69(1H, s), 7_76(1H, s), 7.77(2H, s), 7.77{0H, m), 7.87-7.93(5H, m) , 8.07I1H, s)f (H,) 811.10 810.42 25 δ ·= 0.9(12H, m), 1.91(8H, m), 7.28(1H, m), 7.38~7.41(2H, m), 7.51~7·61(12H, m), 7.69(1H, s), 7.73(2H, m), 7.76(1H, s), 7.77(1H, s), 7.87-8(8H, m), 8.07( 1H, s), 8.13(1H, m> 795.06 794.39 26 δ = 0.9(12H, m), 1.91(8H, m), 7.28(1H, m), 7.38(1H, m), 7.55-7.6K11H, m ), 7.69(1H, s), 7.73(3Η, m), 7.76(1H, s), 7.77(1H, s), 7·87~8(11H, m), 8·07(1Η, s ), 8.13(1H, m) 845.12 844.41 27 δ = 0.9(12H, m), 1.72(6H, s), 1.91(8H, m), 7·28(2Η, m), 7.38{2H, in), 7.55-7.63 (10H, m), 7·69(1Η, s), 7.73(2H, m), 7.76(1H, s), 7.77(2H, s) , 7.77(0H, m), 7.87-8( 10H, m), 8.07(1H, s)f 8.13(1H, m) 911.22 910.45 28 δ = 1_78(6H, s), 7.29(1H, m) , 7.39(2H, m), 7.45-7.5(4H, m), 7.54 (1H, s), 7.58-7.63(9H, m), 7.73(2Hf m)/ 7.76(lHr s) f 7.91-7.92(4H, m) , 8(4H, m), 8.07(1H , s), 8.12I1H, m), 8.85(1H, s), (H,) 711.89 711.29 29 δ = 1.78(6H, s), 7.29(1H, m), 7_41~7.52(9H, m), 7.54 (1H, s), 7.58-7.63(10H, ra), 7.73<2H, m), 7.76(1H, s), 7.92~8(7H, m), 8.07(1H, s), 8.12-8.13( 2H, m), 8.85(1H, s), (H,). 787.98 787.32 30 δ = 1.72(6H, s), 1.78(6H, s), 2.69(6H, s) , 7.28(1H, m), 7.38~7.39(3H, m), 7.55~7.59(7H, m), 7.73(2H, m), 7.76(1H, s), 7.87~7.92(5H, ra), 8 (4H, in), 8.07(1H, s), 690.91 690.33 28 94960 201113238 (Η, , ------ 31 丨 s>, νϋΠ'θ to '丄, ·78,' 2.45(3H, s>, 2.69 (6Η, 7 7~7 7·38(1Ηί 7.55~7.59(7Η, ιη), π·)',8:〇7ίΐΗ: :!: ,7η·76,(1Η,Sh 7·85 ~7·92(4Η, m)/ 6(4Η, 704.94 704.34 32 7 38-7 . S); 7.28<1Η, m), 7 76 (Ϊη if' 7 〇7; 55~7·59(7Η - 7·73(2Η, m), (H^s), 7, 87~7.92{5H,m),8(4H,ir〇,8.07(lH,S), 698.84 698.28 33 m)T 772|5 (ϊΐΗ Π>>ό7·3?( = ο, m)' ?·4(1Η« 7.45~7.5(7Η, 7.91 UH 5ifH/*7 οι \ 7·58"*7-^3(11Η, m ), 7·73(2Η, m), • / S), 7.91-7.92(2Η, m), 8(4Η/ m), 8.12(1Η, m) 760.92 760.29 34 1 7.58~7 63<9Η,, , for example, 7.45, 7.5 (yet m), s) 7 7·73 (2Η^ «Ο» 7.78 (1Η, s), 7.86 (1Η, „) . 14Ά, S), 7·91~7· 92(2Η, m), 8(4Η, m), 8.12(1Η, r -------- 701.87 701.22 35 11 7 /〇!t>H, S), 7.32-v7.39(4H, m), 7.42(1H, s)" 7 7,fi,f2, 7·58~7·59(6Η» m), 7.66(1H, m), 7.73(2H, !),' (H ) 1H,S>,7·89~7·92 (5η^m) / 8(4H, m), 8.07 (1«! 636.78 636.25 [Example 1] Production of 〇LED device using organic electroluminescent compound of the present invention Manufacture of 〇LED using the organic electroluminescent compound of the present invention Device. First, the transparent electrode ΙΤ0 film (15 Ω / Ι:) obtained from OLED glass (manufactured by Samsung Corning) was washed with a mixture of chloroform, propylene, ethanol, and distilled water in the order of ultrasonic waves, and stored in isopropyl alcohol. . Then, the ΙΤ0 substrate was mounted on the substrate of the vacuum vapor deposition apparatus. 4,4,,4"-parade (N,N-(2-naphthyl)-phenylamino)triphenyl "amine (2-TNATA) is placed in a chamber of the vacuum vapor deposition apparatus, The chamber is then ventilated to a vacuum of tΙΟrr (t〇rr), and a current is applied to the chamber to =2-TNATA, thereby forming a chamber having a thickness of 6 〇 nanometer (coffee') on the IT0 substrate, Next, Ν,Ν'-double U-naphthyl)-oxime, Ν'-amine (ΝΡΒ) is placed in another vacuum chamber of the vacuum vapor deposition apparatus, and the electricity is applied to the chamber 94106 29 201113238, and 9 NPB is A hole transport layer having a thickness of 20 nm is formed on the hole injection layer. An electric field luminescent layer is also formed. As a main body, the chamber is formed on the hole transport layer after forming the electric/same main inlet layer and the hole transport layer. Compound 4 was placed in one of the vacuum vapor deposition apparatus' and the compound was placed in another chamber as a dopant. The two materials were evaporated at different speeds to vapor-deposit an electric field luminescent layer having a thickness of 30 nm on the hole transport layer in an amount of 2 to 5% by weight based on the host material.

接著，氣相沈積厚度為20 nm之具下列結構之參（8_ 羥基喹啉）鋁（II I)(Alq)作為電子傳輸層。然後再沈積厚度 為1 run至2 nm之具下列結構之8-羥基喹啉鋰（Lithium qui no late, Li q)作為電子注入層’再使用另真空氣相沈 積裝置形成厚度為150 nm之鋁陰極而製造出〇LED。 用於0LED之各化合物皆於使用前於1〇-6 torr藉由真 空昇華而純化者。 [比較例1]使用傳統電場發光材料0LED之製造 ......广上> & η u制诸0LED裝置，除了於Next, ginseng (8-hydroxyquinoline)aluminum (II I) (Alq) having the following structure was deposited at a thickness of 20 nm as an electron transport layer. Then, Lithium qui no late (Li q) having the following structure and having a thickness of 1 run to 2 nm is deposited as an electron injecting layer', and another vacuum vapor deposition apparatus is used to form aluminum having a thickness of 150 nm. A cathode is fabricated to produce a germanium LED. Each compound used for OLED was purified by vacuum sublimation at 1 〇 to 6 torr before use. [Comparative Example 1] Fabrication using a conventional electroluminescent material OLED [...] 广广>& η u OLED devices, except

94960 201113238 於5, 000燭光（cd)/平方米（m2)測定實施例1及比較例 1所製造之包括本發明有機電場發光化合物之OLED裝置及 傳統電場發光化合物之OLED裝置之發光效率。結果如表2 所示。 表2 編號 主體 摻雜劑 摻雜濃度 (重量％) 發光效率 (cd/安培(A)) 顏色 驅動 電壓 實施例1 4 化合物E 3 18.5 綠色 6.4 實施例1 7 化合物E 3 18.0 綠色 6.8 實施例1 11 化合物E 3 18.1 綠色 6.5 實施例1 16 化合物E 3 18.4 綠色 6.5 實施例1 23 化合物E 3 18.3 綠色 6.7 實施例1 25 化合物E 3 18.1 綠色 6.4 實施例1 29 化合物E 3 18.0 綠色 6.8 實施例1 30 化合物E 3 18.3 綠色 6.5 實施例1 33 化合物E 3 13.1 綠色 7.0 實施例1 35 化合物E 3 18.2 綠色 6.9 比較例1 DNA 化合物E 3 16.3 綠色 7.2 由表2可以看出，將本發明之材料應用於綠色發光裝 置之結果顯示，與比較例1之結果相比，驅動電壓降低及 發光效率改進且同時保持相同或較高的色純度。 【圖式簡單說明】 無 【主要元件符號說明】 無 31 9496094960 201113238 The luminous efficiency of the OLED device comprising the organic electroluminescent compound of the present invention and the OLED device of the conventional electroluminescent compound produced in Example 1 and Comparative Example 1 was measured at 5,000 candelas (cd) per square meter (m2). The results are shown in Table 2. Table 2 No. Main body dopant doping concentration (% by weight) Luminous efficiency (cd/ampere (A)) Color driving voltage Example 1 4 Compound E 3 18.5 Green 6.4 Example 1 7 Compound E 3 18.0 Green 6.8 Example 1 11 Compound E 3 18.1 Green 6.5 Example 1 16 Compound E 3 18.4 Green 6.5 Example 1 23 Compound E 3 18.3 Green 6.7 Example 1 25 Compound E 3 18.1 Green 6.4 Example 1 29 Compound E 3 18.0 Green 6.8 Example 1 30 Compound E 3 18.3 Green 6.5 Example 1 33 Compound E 3 13.1 Green 7.0 Example 1 35 Compound E 3 18.2 Green 6.9 Comparative Example 1 DNA Compound E 3 16.3 Green 7.2 As can be seen from Table 2, the material of the present invention was applied. As a result of the green light-emitting device, it was revealed that the driving voltage was lowered and the luminous efficiency was improved as compared with the result of Comparative Example 1 while maintaining the same or higher color purity. [Simple description of the diagram] None [Key component symbol description] None 31 94960

Claims (1)

201113238 七、申請專利範圍： I. -種化學式1所表示之有機電場發光化合物·· 化學式1201113238 VII. Patent application scope: I. - Organic electric field luminescent compound represented by chemical formula 1 · Chemical formula 1 ”中1至Rh獨立表不氫、氛、虐素、具有或不具有 取代基之（C1-C30)貌基、具有或不具有取代基之 (C6-C3G)芳基、與—個衫個具有或不具有取代基之 (C3-C3G)環絲料之經取代絲經取代（G6_c3〇)芳 基、具有或不具有取代基之雜芳基、具有或不 二有取代基之5員至7員雜環院基、與一個或多個具有 或不具有取代基之芳香環龄之5員至7員雜環院基、 具有或不具有取代基之（C3_C3〇)環烷基、與一個或多個 具有或不具有取代基之芳香環稠合之（C3_C3〇)環烷 基、氰基、胺基、具有或不具有取代基之（cl_C3〇)烷基 胺基、具有或不具有取代基之（C6_C3〇)芳基胺基、 NR21R22 ' BR23R24' PR25R26 ' P(=〇)R27R28 &gt; RaRbRcSi- &gt; RdY- ' ReC(=0)-、RfC(=0)0-、具有或不具有取代基之(；C6_C3〇) 芳基（C1-C30)烷基、具有或不具有取代基之（C2-C30) 烯基、具有或不具有取代基之（C2-C30)炔基、具有或不 具有取代基之（C6-C30)芳氧基羰基、具有或不具有取代 基之（C1-C30)烧氧基魏氧基、具有或不具有取代基之 (C1-C30)烷基羰氧基、具有或不具有取代基之（C6-C30) 32 94960 201113238 fjk 芳基羰氧基'具有或不具有取代基之（C6_c3〇)芳氧基 氣基、則基，你?2、减 或羥基， 或者1^至Rh可各自經由具有或不具有稠合環之 (C3-C30)伸院基或（C3_C30)伸稀基鍵聯至相鄰 以形成脂環、或單環或多環之芳香環； ^ X、Y 及 w 獨立表示_(CR5lR52)m_、—（Rs 姻……ο-、佩)(R55^^^ 、ρ(=〇)(Μ-、-c(=0)-或-B(R58)- ; 56 Rsi至R58及1^至R63係如匕至Ru所定義； ~雜環烧基或雜芳基可含有一個或多個選自B、 S、P(=0)、Si及p之雜原子 ;以及 :至R28獨立表示具有或不具有取代基之(C卜C聊 =具有或不具有取代基之⑽·)芳基或 : 有取代基之（C3-C30)雜芳基； 次不，、 R、Kb、r及Rd獨立表示具有或不具有取代基之（ 义基或具有或不具有取代基之（C6_C30)芳基； Y表示S或0; Re f R表不具有或不具有取代基之（C1〜C3 2不具有取代基之（(：1.)烧氧基、具有^二有取 芳芳基或具有或不具有取代基之(c6翁 m表示整數1或2。 94960 33 201113238 2.如申請專利範圍第1項所述之有機電場發光化合物，其 中，於‘具有或不具有取代基，中，Ri至Rh、R21至r28、 R”至R58及hi至R63之取代基係進一步經一個或多個選 自下列所組成群組之取代基取代：氘、函素、具有或不 具有鹵素取代基之（C1-C30)烷基、（C6-C30)芳基、具有 或不具有（C6-C30)芳基取代基之（C3-C30)雜芳基、5員 至7員雜環烷基、與一個或多個芳香環稠合之5員至7 員雜環烧基、（C3-C30)環烧基、與一個或多個芳香環稠 合之（C3-C30)環烷基、三（C1-C30)烷基矽烷基、二 (C1-C30)烷基（C6-C30)芳基矽烷基、三（C6-C30)芳基石夕 烧基、（C2-C30)稀基、（C2-C30)快基、氮基、n卡β坐基、 NR31R32、BR33R34、PR35R36、p(=〇)R37R38、（C6-C30)芳基 (C1-C30)烷基、（C1-C30)烷基（C6-C30)芳基、（C1-C30) 烧氧基、（C1-C30)院硫基、（C6-C30)芳氧基、（C6-C30) 芳硫基、（C1-C30)烧氧基幾基、（C1-C30)烧基幾基、 (C6-C30)芳基羰基、（C6_C30)芳氧基羰基、（c卜C3〇) 烷氧基羰氧基、（C1-C30)烷基羰氧基、（C6_C3〇)芳基羰 氧基、（C6-C30)芳氧基羰氧基、羧基、硝基及羥基；或 者該取代基係鍵聯至相鄰取代基以形成環；以及 r31至^獨立表示（C1_C30)烷基、（C6_C30)芳基或 (C3-C30)雜芳基。 3·.如申請專利範圍第丨項所述之有機電場發光化合物，其 中’ Ri至Ru係選自下列結構： 34 94960 201113238 ^丨》"S1 to Rh independently represent hydrogen (C1-C30) phenanthrene, (C6-C3G) aryl group with or without a substituent, and a shirt Substituted filaments of (C3-C3G) cyclofilaments with or without substituents substituted with (G6_c3〇)aryl, heteroaryl with or without substituents, 5 members with or without substituents a 7-membered heterocyclic compound, a 5- to 7-membered heterocyclic compound having one or more aromatic ring ages with or without a substituent, a (C3_C3〇)cycloalkyl group with or without a substituent, and one Or a (C3_C3〇)cycloalkyl group fused with an aromatic ring having or without a substituent, a cyano group, an amine group, a (cl_C3〇)alkylamino group with or without a substituent, with or without a substitution (C6_C3〇) arylamine group, NR21R22 'BR23R24' PR25R26 'P(=〇)R27R28 &gt; RaRbRcSi- &gt; RdY- ' ReC(=0)-, RfC(=0)0-, with or without a (C1-C30)alkyl group having a substituent (C6-C3〇), a (C2-C30) alkenyl group having or not having a substituent, a (C2-C30) alkynyl group having or not having a substituent, having or not a (C6-C30) aryloxycarbonyl group having a substituent, a (C1-C30) alkoxyoxy group having or not having a substituent, and a (C1-C30) alkylcarbonyloxy group having or not having a substituent With or without a substituent (C6-C30) 32 94960 201113238 fjk arylcarbonyloxy '(C6_c3〇) aryloxy gas group with or without a substituent, a group, a ?2, a minus or a hydroxy group , or 1^ to Rh may each be bonded to adjacent via a (C3-C30) stretching group or a (C3_C30) stretching group with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic Ring; ^ X, Y, and w independently represent _(CR5lR52)m_, -(Rs marriage... ο-, 佩)(R55^^^, ρ(=〇)(Μ-, -c(=0)- or -B(R58)-; 56 Rsi to R58 and 1^ to R63 are as defined for Ru to Ru; ~Heterocyclic alkyl or heteroaryl may contain one or more selected from B, S, P (=0) , Si and p heteroatoms; and: to R28 independently represent with or without a substituent (CBu C chat = (10)· with or without a substituent) aryl or: substituted (C3-C30) Heteroaryl; sub-, R, Kb, r and Rd independently represent with or without a substituent (Y-based or (C6_C30) aryl group with or without a substituent; Y represents S or 0; Re f R has no or no substituent (C1 to C3 2 does not have a substituent ((:1. An alkoxy group having a aryl group or having a substituent (c6) m represents an integer of 1 or 2. 2. The organic electroluminescent compound according to claim 1, wherein, in the presence or absence of a substituent, Ri to Rh, R21 to r28, R" to R58 and hi to R63 The substituent system is further substituted with one or more substituents selected from the group consisting of ruthenium, a fluorene, a (C1-C30)alkyl group having or without a halogen substituent, a (C6-C30) aryl group, (C3-C30)heteroaryl group with or without (C6-C30) aryl substituent, 5- to 7-membered heterocycloalkyl group, 5- to 7-membered heterocyclic ring fused to one or more aromatic rings An alkyl group, a (C3-C30) cycloalkyl group, a (C3-C30) cycloalkyl group fused to one or more aromatic rings, a tri(C1-C30)alkyldecane group, a di(C1-C30)alkyl group. (C6-C30) aryl decyl, tris(C6-C30) aryl sulphate, (C2-C30), (C2-C30) fast group, nitrogen group, n-card β-sitting group, NR31R32, BR33R34 , PR35R36, p(=〇)R37R38, (C6-C30) aryl (C1-C30) alkyl, (C1-C30)alkyl (C6-C30) aryl, (C1-C30) alkoxy, ( C1-C30) Institute of sulfur, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) Alkoxy group, (C1-C30) alkyl group, (C6-C30) arylcarbonyl group, (C6_C30) aryloxycarbonyl group, (c-C3〇) alkoxycarbonyloxy group, (C1-C30 An alkylcarbonyloxy group, (C6_C3〇)arylcarbonyloxy group, (C6-C30)aryloxycarbonyloxy group, a carboxyl group, a nitro group and a hydroxyl group; or the substituent is bonded to an adjacent substituent to form And R31 to ^ independently represent (C1_C30)alkyl, (C6_C30) aryl or (C3-C30)heteroaryl. 3. The organic electroluminescent compound according to claim </ RTI> wherein ' Ri To Ru is selected from the following structures: 34 94960 201113238 ^丨 其中， 至R132獨立表示氫、氘、鹵素、（Cl-C30)烷基、（C6-C30) 芳基、與一個或多個（C3-C30)環烷基稠合之（C6-C30) 芳基、（C3-C30)雜芳基、5員至7員雜環烷基、與一個 或多個芳香環稠合之5員至7員雜環烷基、（C3-C30) 環烷基、與一個或多個芳香環稠合之（C3-C30)環烷基、 氰基、胺基、（C1-C30)烷基胺基、（C6-C30)芳基胺基、 NR41R42、BR43R44、PR45R46、P(=0)R47R48、三（C1-C30)烧基 砂烷基、二（C1-C30)烷基（C6-C30)芳基矽烷基、三 (C6-C30)芳基矽烷基、（C6-C30)芳基（(n_C30)烧基、 (C1-C30)烧氧基、（C1-C30)烧硫基、（C6-C30)芳氧基、 94960 35 201113238 (C6-C30)芳硫基、（C1-C30)烷氧基羰基、（cl—C3〇)燒義 羰基、（C6-C30)芳基羰基、（C2-C30)烯基、 炔基、（C6-C30)芳氧基羰基、（C1-C30)烷氧基羰氧基、 (C1-C30)烷基羰氧基、（C6-C30)芳基羰氧基、（(：6〜^叼 芳氧基裁氧基、羧基、硝基或羥基；或者^至Κι”可 經由具有或不具有稠合環之（C3-C30)伸烧基或（C3~C3〇；) 伸烯基鍵聯至相鄰取代基以形成脂環或單環或多環之 芳香環；以及 心至r48獨立表示（C1_C30)烷基、（C6_C3〇)芳基或 (C3-C30)雜芳基。 4.如申請專利範圍第3項所述之有機電場發光化合物，其 中’ L至Rh係選自下列結構： H3C-I &quot;I o-l H3C^Q-| H3C0h| nch〇k| phS^i &amp;l &amp;丨 0^1 办丨 0-|汾1Wherein, to R132 independently represents hydrogen, hydrazine, halogen, (Cl-C30) alkyl, (C6-C30) aryl, fused to one or more (C3-C30) cycloalkyl (C6-C30) aryl a (C3-C30)heteroaryl group, a 5- to 7-membered heterocycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings, (C3-C30)cycloalkyl, (C3-C30)cycloalkyl, cyano, amine, (C1-C30)alkylamino, (C6-C30) arylamino, NR41R42, BR43R44, PR45R46 fused to one or more aromatic rings , P(=0)R47R48, tris(C1-C30)alkylalkyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl, C6-C30) aryl ((n_C30) alkyl, (C1-C30) alkoxy, (C1-C30) sulfur-burning, (C6-C30) aryloxy, 94960 35 201113238 (C6-C30) aromatic sulfur (C1-C30) alkoxycarbonyl, (cl-C3〇)-sintered carbonyl, (C6-C30) arylcarbonyl, (C2-C30)alkenyl, alkynyl, (C6-C30) aryloxy Carbonyl group, (C1-C30) alkoxycarbonyloxy group, (C1-C30) alkylcarbonyloxy group, (C6-C30) arylcarbonyloxy group, ((:6~^叼 aryloxy alkoxy group, Carboxyl, nitro or a group; or ^ to Κι" may be bonded to an adjacent substituent via an (Alkenyl) group having or without a fused ring (C3-C30) or (C3~C3〇;) to form an alicyclic or monocyclic ring. Or a polycyclic aromatic ring; and a heart to r48 independently represents a (C1_C30) alkyl group, a (C6_C3〇) aryl group or a (C3-C30) heteroaryl group. 4. The organic electric field luminescence as described in claim 3 a compound wherein 'L to Rh is selected from the following structures: H3C-I &quot;I ol H3C^Q-| H3C0h| nch〇k| phS^i &amp;l &amp;丨0^1 丨0-|汾1 5.如申請專利範圍第1項所述之有機電場發光化合物，其 係選自下列結構： 36 94960 2011132385. The organic electroluminescent compound according to claim 1, which is selected from the following structures: 36 94960 201113238 s 37 94960 201113238s 37 94960 201113238 6. —種包括如申請專利範圍第1項至第5項中任一項所3 之有機電場發光化合物之有機電場發光裝置。 7. 如申請專利範圍第6項所述之有機電場發光裝置，其( 各第電極，第二電極；以及一層或多層插置於該第_ 電極與該第二電極間之有機層；其中，該有機層包括一 種或多種如申請專利範圍第1項至第5項中任一項則 發光化合物以及一種或多種化學式2或社 学式3所表示之摻雜劑·· 94960 38 (2)201113238An organic electric field light-emitting device comprising an organic electroluminescent compound according to any one of claims 1 to 5. 7. The organic electroluminescent device of claim 6, wherein each of the first electrode and the second electrode; and one or more layers are interposed between the first electrode and the second electrode; wherein The organic layer includes one or more luminescent compounds as disclosed in any one of claims 1 to 5 and one or more dopants represented by Chemical Formula 2 or Social Formula 3·· 94960 38 (2) 201113238 (3) 其中，Arn及An2獨立表示具有或不具有取代基之 (C1-C30)烷基、具有或不具有取代基之（C6-C30)芳基、 具有或不具有取代基之（C4-C30)雜芳基、具有或不具有 取代基之（C6-C30)芳基胺基、（C1-C30)烷基胺基、具有 或不具有取代基之5員至7員雜環烷基、與一個或多個 具有或不具有取代基之芳香環稠合之5員至7員雜環烷 基、具有或不具有取代基之（C3-C30)環烷基或與一個或 多個具有或不具有取代基之芳香環稠合之（C3-C30)環 烷基，或者Arn與An2可經由具有或不具有稠合環之 (C3-C30)伸烷基或（C3-C30)伸烯基相鍵聯以形成脂 環、或單環或多環之芳香環； 當c為1時，An3表示具有或不具有取代基之（C6-C30) 芳基、具有或不具有取代基之（C4-C30)雜芳基或選自下 列結構之取代基； ^201(3) wherein, Arn and An2 independently represent (C1-C30)alkyl group having or without a substituent, (C6-C30) aryl group having or without a substituent, with or without a substituent (C4- C30) a heteroaryl group, a (C6-C30) arylamino group having or not having a substituent, a (C1-C30)alkylamino group, a 5- to 7-membered heterocycloalkyl group having or not having a substituent, 5- to 7-membered heterocycloalkyl fused to one or more aromatic rings with or without a substituent, (C3-C30) cycloalkyl with or without a substituent or with one or more An aromatic ring fused (C3-C30) cycloalkyl group having no substituent, or Arn and An2 may be extended to a (C3-C30) alkyl group or (C3-C30) with or without a fused ring Phase-bonded to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when c is 1, An3 represents a (C6-C30) aryl group with or without a substituent, with or without a substituent (C4 -C30) a heteroaryl group or a substituent selected from the following structures; ^201 Ar七! 只2〇1 一=-Ar 1 s 當c為2時，An3表示具有或不具有取代基之（C6-C30) 伸芳基、具有或不具有取代基之（C4-C30)伸雜芳基或選 39 94960 201113238 自下列結構之取代基；Ar seven! Only 2〇1 ==Ar 1 s When c is 2, An3 represents (C6-C30) extended aryl group with or without a substituent (C4-C30) with or without a substituent Heteroaryl or Y. 39 94960 201113238 Substituents from the following structures; Ari4及Ari5表示具有或不具有取代基之（C6-C30)伸芳基 或具有或不具有取代基之（C4-C30)伸雜芳基； R2〇1至R2G3獨立表示氫、氘、具有或不具有取代基之 (C1-C30)烷基或具有或不具有取代基之（C6-C30)芳基； d表示1至4之整數；以及 e表示整數0或1。 8. 如申請專利範圍第7項所述之有機電場發光裝置，其 中，該有機層進一步包括一種或多種選自芳基胺化合物 及苯乙烯基芳基胺化合物所組成群組之胺化合物，或一 種或多種選自第1族之有機金屬、第2族、第4周期與 第5周期之過渡金屬、鑭系金屬及d-過渡元素所組成 群組之金屬或錯合物化合物。 9. 如申請專利範圍第7項所述之有機電場發光裝置，其 中，該有機層包括電場發光層及電荷產生層。 10. 如申請專利範圍第7項所述之有機電場發光裝置，其為 白色發光有機電場發光裝置，其中，該有機層包括一層 或多層同時發出藍光、紅光或綠光之有機電場發光層。 40 94960 201113238 四、 指定代表圖：本案無圖式 (一) 本案指定代表圖為：第（）圖。 (二) 本代表圖之元件符號簡單說明： 五、 本案若有化學式時，請揭示最能顯示發明特徵的化學式： 化學式1Ari4 and Ari5 represent a (C6-C30) extended aryl group with or without a substituent or a (C4-C30) heteroaryl group with or without a substituent; R2〇1 to R2G3 independently represent hydrogen, deuterium, or (C1-C30)alkyl group having no substituent or (C6-C30) aryl group having or without a substituent; d represents an integer of 1 to 4; and e represents an integer of 0 or 1. 8. The organic electroluminescent device of claim 7, wherein the organic layer further comprises one or more amine compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds, or One or more metals or complex compounds selected from the group consisting of organometallics of Group 1, Group 2, transition metals of the fourth and fifth cycles, lanthanide metals, and d-transition elements. 9. The organic electroluminescent device of claim 7, wherein the organic layer comprises an electric field luminescent layer and a charge generating layer. 10. The organic electroluminescent device of claim 7, which is a white light-emitting organic electric field light-emitting device, wherein the organic layer comprises one or more layers of an organic electric field light-emitting layer that simultaneously emits blue light, red light or green light. 40 94960 201113238 IV. Designation of representative map: There is no schema in this case (1) The representative representative figure of this case is: (). (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: Chemical Formula 1 2 949602 94960
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