TW201204807A - 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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TW201204807A
TW201204807A TW100106624A TW100106624A TW201204807A TW 201204807 A TW201204807 A TW 201204807A TW 100106624 A TW100106624 A TW 100106624A TW 100106624 A TW100106624 A TW 100106624A TW 201204807 A TW201204807 A TW 201204807A
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Sung-Jin Eum
Hyuck-Joo Kwon
Bong-Ok Kim
Sung-Min Kim
Seung-Soo Yoon
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Rohm & Haas Elect Mat
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Abstract

Provided are novel organic electroluminescent compounds, and organic electroluminescent devices comprising the same. Since the organic electroluminescent compounds exhibit high luminous efficiency in blue color, and excellent life property of the material, they may be used to manufacture OLEDs having very good operation life.

Description

201204807 六、發明說明： 【發明所屬之技術領域】 本發明係相關於-種新賴有機電場發光化合物，及使 合物之有機電場發光裝置，更特別的是，相關於-辦為電場發储料之新穎有機電場發光化合物，以及使 用°亥化合物作為摻雜劑之有機電場發光裝置， 【先前技術】 在顯示器裝置中201204807 VI. Description of the Invention: [Technical Field] The present invention relates to an organic electric field illuminating device, and an organic electric field illuminating device, and more particularly, related to electric field storage a novel organic electroluminescent compound, and an organic electric field illuminating device using a compound as a dopant, [Prior Art] in a display device

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—·電琢發光（electroluminescent, EI 裝置作為自發光顯示器裝置之優點為可提供廣視角、良好 ^ Ϊ ’以及快速的應答速度。在198 7年，Eastman Kodak =展出❹低分子量之料二胺與狀錯合物作為形 成電场發光層之物質之有舰裝置[細伽· ^ 913， 1987]。 在有機EL裝置中，決定其表現（包括發光效率與操作 』）之最重残素為電場發域料。對於電場發光材料之某 些要求包括在固態時之高縣量子產率、高電子與電洞移 動性、在真空沈積時之抗分解性、可形成均勻薄膜之能力， 以及穩定性。 有機電場發光材料一般可分類為高分子量材料與低 分子量材料。就分子結構觀點而言，該低分子量材料包括 金屬錯合物’以及不含金屬之完全有機的電場發光材料。 此類電場發光材料包括嵌合式錯合物，如三（8_經基喧琳） 紹錯合物、香豆素（e(3umarin)衍生物、四苯基了二稀衍生 物、雙（苯乙烯基伸芳基）（bis(styrylary丨ene))衍生物， 95143 3 201204807 以及噚二唑衍生物。已報導這些材料可發出由藍光至紅光 之可見光範圍光線，因此預期可獲得全彩顯示裝置。 同時’就傳統藍光材料而言，自從Idemitsu-Kosan 發展出二苯基乙烯基—聯苯（DPVBi)(化合物a)以來，已有 夕種材料被發展出且已商業化。除了 Idemi tsu-Kosan之藍 光材料系統外，Kodac之二萘基蒽（DNA)(化合物〇、四（第 二丁基）茈（化合物c)系統或其類似物亦為已知。然而，這 些材料目前仍需要大量的研究與發展。— Electroluminescence (electroluminescent, EI device as a self-luminous display device has the advantage of providing a wide viewing angle, good ^ Ϊ ' and fast response speed. In 198, Eastman Kodak = exhibiting low molecular weight diamine A complex device as a material for forming an electric field luminescent layer [Ji Ga· ^ 913, 1987]. In an organic EL device, the most important residue for determining its performance (including luminous efficiency and operation) is Electric field emission materials. Some requirements for electric field luminescent materials include high county quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form a uniform film, and stability Organic electroluminescent materials are generally classified into high molecular weight materials and low molecular weight materials. From a molecular structural point of view, the low molecular weight materials include metal complexes and metal-free fully organic electroluminescent materials. Luminescent materials include chimeric complexes such as tris(8-)-based conjugates, coumarins (e(3umarin) derivatives, tetraphenyl-diuretic derivatives) , bis(styrylary 丨ene) derivatives, 95143 3 201204807 and oxadiazole derivatives. These materials have been reported to emit light in the visible range from blue to red, so it is expected to be available. Full color display device. Meanwhile, in the case of conventional blue light materials, since Idemitsu-Kosan developed diphenylvinyl-biphenyl (DPVBi) (compound a), materials have been developed and commercialized. In addition to the blue light material system of Idemi tsu-Kosan, Kodap's dinaphthyl quinone (DNA) (compound oxime, tetra(t-butyl) hydrazine (compound c) system or analogs thereof are also known. However, these materials A lot of research and development is still needed.

Idemitsu-Kosan的桂皮基（distryl)化合物系統（已 知為目前具有最高效率者）具有6 lm/w之功率效率（ρ〇· efficiency)，以及大於3〇, 〇〇〇小時之有用裝置壽命。然 而’當其應用於全彩_科，壽命僅有數千小時，這是 因為其色彩純度會隨著操作時間而降低。 就藍光電場發光而言，若電場發光波長向更長波長 微位移-些，此現象卻變成發光效率上之優點，而， 佳’仍不易將該材料應用至高品質之顯 .上。此外’由於色彩純度、效率與熱穩定性之問題， 前此類材料之研究與發展相當急切。Idemitsu-Kosan's distryl compound system (known as the current highest efficiency) has a power efficiency of 6 lm/w and a useful device life of more than 3 〇. However, when it is applied to the full color, the lifespan is only a few thousand hours, because its color purity will decrease with the operation time. In the case of blue-field electric field illumination, if the electric field emission wavelength is slightly displaced to a longer wavelength, this phenomenon becomes an advantage in luminous efficiency, and it is still difficult to apply the material to high-quality display. In addition, due to the problems of color purity, efficiency and thermal stability, the research and development of such materials is quite urgent.

95143 4 201204807 L發明内容】 技術問題 在努力纽上述賴技狀叫後，本㈣人發展出 斤穎之電場發光化合物，其實現具有 大幅增進之壽命性質之有機電場發光駿置、’效率’與 摻雜= 化合物，其與傳統 好色座標之Μ，^ 餘置壽命及良 妒署 ’、克服上述問題，並提供有機電場發光 具有高發光效率與增進之壽命性f。 九 技術解決方案 係提供新穎之有機電場發光化合物，以及包含該化合 化人二场發光裝置。具體地，本發明之有機電場發光 具有古化予式1或2表示。由於該有機電場發光化合物 π»發光效率與絕佳之材料壽命性質，因此可用於製 、非常良好操作期之0LED。 化學式1 (Rl)a95143 4 201204807 LSummary of the Invention] Technical Issues After the hard work of the above-mentioned technology, the (4) people developed the electric field luminescent compound of Jinying, which realizes the organic electric field illuminating, 'efficiency' with greatly improved life properties. Doping = compound, which is consistent with traditional chromatic coordinates, ^ Remaining lifetime and good work, overcomes the above problems, and provides organic luminescence with high luminous efficiency and improved lifetime f. Nine technical solutions provide novel organic electroluminescent compounds, as well as including the chemical human two-field illumination device. Specifically, the organic electric field luminescence of the present invention is represented by the formula 1 or 2. Due to the π» luminescence efficiency of the organic electroluminescent compound and excellent material lifetime properties, it can be used for OLEDs with very good operation period. Chemical formula 1 (Rl)a

5 95143 201204807 其中5 95143 201204807 where

Ri至R5獨立地表示氫、（a-C60)烷基、（C3-C60)環烷 基、（C6-C60)芳基、含有一個或多個雜原子之（C2-C60)雜 芳基（該雜原子選自N、0、S、P、Si與Se)、（(n-C60)烷 氧基、（C1-C60)烷基硫基、（C6-C60)芳基氧基、（C6-C60) 芳基硫基、（C6-C30)芳基（C1-C30)烷基胺基、三（C1-C30) 烷基矽基（tri(Cl-C30)alkylsilyl))、二（C1-C30)烷基 (C6-C30)芳基矽基、或三（C6-C30)芳基矽基； X 表示化學鍵、-(CReR?%-、-N(Re)-、-Si(R9)(Ri。）-、 -0-、-S-、-Se-、或-(DCsWRi〗)-; 仏至R1Z獨立地表示氫、（C1-C60)烷基、（C3-C60)環烷 基、（C6-C60)芳基、含有一個或多個雜原子之（C2-C60)雜 芳基（該雜原子選自N、0、S、Si與Se)、（C1-C60)烧氧基、 (n-C60)烷基硫基、（C6-C60)芳基氧基、（C6-C60)芳基硫 基、單-或二-(C1-C60)烷基胺基、單-或二-(C6-C60)芳基 胺基、（C6-C30)芳基（C1-C30)烷基胺基、三（C1-C30)烷基 矽基、二（C1-C30)烷基（C6-C30)芳基矽基、或三（C6-C30) 芳基石夕基；或Re與R?、R9與Ri〇及Rn與Ri2經由具有或不具 稠合環之（C3-C60)伸烷基或（C3-C60)伸烯基聯結以形成脂 肪環、或單環或多環之芳香環； Y表示（C6-C60)伸芳基、伸金剛烧基、含有一個或多 個雜原子之（C3-C60)雜伸芳基（該雜原子選自n、〇、S、P、Ri to R5 independently represent hydrogen, (a-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl, (C2-C60)heteroaryl containing one or more heteroatoms ( The hetero atom is selected from the group consisting of N, 0, S, P, Si and Se), ((n-C60) alkoxy, (C1-C60)alkylthio, (C6-C60) aryloxy, (C6 -C60) arylthio group, (C6-C30) aryl (C1-C30) alkylamino group, tri(C1-C30)alkyl fluorenyl (tri(Cl-C30)alkylsilyl)), di(C1- C30) alkyl (C6-C30) aryl fluorenyl, or tri(C6-C30) aryl fluorenyl; X represents a chemical bond, -(CReR?%-, -N(Re)-, -Si(R9)( Ri.)-, -0-, -S-, -Se-, or -(DCsWRi)-; 仏 to R1Z independently represent hydrogen, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60) aryl, (C2-C60)heteroaryl containing one or more heteroatoms (selected from N, 0, S, Si and Se), (C1-C60) alkoxy, (n-C60)alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, mono- or di-(C1-C60)alkylamino, mono- or di- (C6-C60) arylamino group, (C6-C30) aryl (C1-C30) alkylamino group, tri(C1-C30)alkyldecyl group, di(C1-C30) alkane (C6-C30) aryl fluorenyl, or tris(C6-C30) aryl sylylene; or Re and R?, R9 and Ri 〇 and Rn and Ri2 via (C3-C60) with or without a fused ring An alkyl group or a (C3-C60)alkylene group is bonded to form an aliphatic ring, or a monocyclic or polycyclic aromatic ring; Y represents a (C6-C60) extended aryl group, an exo-alkali group, and contains one or more heteroatoms. (C3-C60) heteroaryl (this hetero atom is selected from n, 〇, S, P,

Si 與 Se)、 6 95143 201204807 芳基（該 Υι表示含有一個或多個雜原子之（C2-60)雜伸 雜原子選自^1、0、8、？、8]1與36); 2!與冗2係獨立地表示化學鍵、-(CR13R14)n〜、、N(Ri5)_、 -Si(Ri6)(Ri7)-、-〇-、-S-、-Se-或_(Ri8)C=C(R19)、，限制 條件為冗1與Z2非同時為化學鍵；Si and Se), 6 95143 201204807 aryl (the ι denotes a (C2-60) hetero-hetero atom containing one or more heteroatoms selected from ^1, 0, 8, ?, 8] 1 and 36); ! Indicates a chemical bond independently of the redundant 2, -(CR13R14)n~, N(Ri5)_, -Si(Ri6)(Ri7)-, -〇-, -S-, -Se-, or _(Ri8) C=C(R19), the constraint is that the redundant 1 and Z2 are not chemical bonds at the same time;

Ri3至Rig獨立地表示氩、（C1-C60)烧基、（C3—C60)環 燒基、（C6-C60)芳基、含有一個或多個雜原子之（c2_c6〇) 雜芳基（該雜原子選自N、0、S、Si與Se)、（C1-C60)烧氧 基、（C1-C60)烷基硫基、（C6-C60)芳基氧基、（C6_C6〇)芳 基硫基、單-或二-(C1-C60)烷基胺基、單-或二-(C6_C6〇；) 芳基胺基、（C6-C30)芳基（C1-C30)烷基胺基、三（cl_C3〇；) 烷基矽基、二（C1-C30)烷基（C6-C30)芳基矽基、或三 (C6-C30)芳基矽基；或心與Ri4、Ri6與Rn，以及Ri8與心 經由具有或不具稠合環之（C3-C60)伸烷基或（C3-C60)烯基 聯結以形成脂肪環、或單環或多環之芳香環； a、b與c獨立地表示1至4之整數； d表示1至3之整數；以及 m與η獨立地表示1至4之整數。 【實施方式】 、在本發明中烷基"、"烷氧基"與其他包括"烷基"部 刀之取代基，包括直鏈或分支鏈兩種。本文所述術語"芳 基係心自芳香經去掉—個氫原子而衍生之有機基。每一環 包括單環或铜合環系統，包括4至7，較佳5至6個環原 子°芳基之具體範例包括苯基、萘基、聯苯基、蒽基、茚 7 95143 201204807 基、苐基、菲基、聯伸三苯基（triphenylenyl)、芘基、花 基、蒯基（chrysenyl)、稠四苯基（naphthacenyl)與丙二歸 合苐基（fluoranthenyl)，但不受限於此。 本文所述術語"雜芳基"係指包括有為芳香環骨架原 子之1至4個選自N、0、S、P、Si與Se之雜原子，以及 作為剩餘芳香環骨架原子之碳原子之芳基。該雜芳基可為 5-或6-元單環雜芳基或與一個或多個苯環稠合之多環雜 芳基，且可部分飽和。 該雜芳基可包括二價芳基，其上之雜原子經氧化或四 級化，形成N-氧化物、四級鹽類或類似物。雜芳基之具體 犯例包括单環雜方基’如e夫喃基、嗟吩基、π比P各基、0米唾 基、吡唑基、噻唑基、噻二唑基、異噻唑基、異噚唑基、 曙唑基、噚二唑基、三哄基、四畊基、三唑基、四唑基、 呋吖基、吡啶基、吡哄基、嘧啶基、嗒畊基；多環雜芳基 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、苯并異噚唑基、苯并噚唑基、 異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異 琳基、噌琳基（cinnolinyl)、哇唾琳基、嗤畊基、啥曙 琳基、°卡°坐、啡π定基與苯并二曙呃基（benzodioxolyl);以 及相應之N-氧化物（如π比咬N-氧化物、喧琳N-氧化物）， 以及其四級鹽類；但不受限於此。 本文所述之包含"（C1-C60)烷基"部分之取代基，可包 含1至60個碳原子、1至20個碳原子’或1至1〇個碳原 子。包含"（C6-C60)芳基"部分之取代基，可包含6至6〇 8 95143 201204807 個炭原子、6至20個碳原子，或6至Μ個碳原子。包含 (C3-C6G)雜芳基，，部分之取代基，可包含3至60個碳原 =、4至20個碳原子’或4至12個碳原子。包含，'（C3_C60) 環，基"部分之取代基，可包含3至⑽個韻子、3至2〇 =碳原子，或3至7個碳原子。包含"（C2_⑽清基或快基 ”部分之取代基，可包含2至6〇個碳原子、2至2〇個碳原 子’或2至1〇個碳原子。 /表示1，2-伸苯基、l 3_伸苯基、u 4_伸苯基、^ 2_ 伸萘基、1，3-伸萘基、1>4一伸萘基、仏伸蔡基、16^申 萘基、1，7-伸萘基、！，8_伸萘基、2, 3_伸萘基、& 6_伸萘 基、2, 7-伸萘基、u 2_伸蒽基、i，3_伸葱基、*一伸葱基、、 1’ 伸蒽基、1，6-伸蒽基、I 7—伸蒽基、u 8_伸蒽基:二 伸蒽基、丨，10一伸蒽基、2, 3-伸蒽基、2, 6-伸蒽基、2厂 伸葱基、2, 9-伸蒽基、2, 1 〇-伸蒽基、9, j 伸| & 伸聯苯基、4, 3，-伸聯苯基、4, 4，-伸聯苯基、！將— -贫苴η。 丨，t伸聯伸 二本丞U，2-tnhenylenyl)、1，3-伸聯伸 聯伸三聯伸三笨基、…伸聯二：’二 伸聯伸二本基、U0—伸聯伸三笨基、u卜伸聯伸三 1 ’ 12-伸聯伸三苯基、2, 3_伸聯伸三笨基、2，^ 基、2, 7-伸聯伸三苯基、2,丨卜伸聯伸三苯基、1 二笨 婦合第基（1，2-fluoranthenylene)、1，3-伸丙一祕丙一 基、1，4-伸兩二烯合祕、1>5-伸丙二稀合第基、、，第 丙二稀合IS基、1，7-伸丙二烯合g基、U8 ^ ’6〜伸 基、1，9-伸两二烯合葬基、uh申丙二稀合第歸合第 2, 3- 95143 9 201204807 201204807 '稀合 2, 9- •歸合 3, 9- 稀合 ::一 2烯二!基、2’4'伸丙二烯合g基、2,5_伸丙 稀合第基、2,8-伸丙二綱基 第基一 3 =基、2，1〇一伸丙二稀合第基、3,4-伸丙 ^基、3, 7-伸丙二烯合第基、3,8—伸丙二稀合第基 伸丙二稀合苐基、3，1M申丙 ## 7 η ^ ’ 口弗 U，8-伸丙二烯 < 二稀合$基、Μ，丙二稀合第基、“_ 伸丙:她、U韻、U部^ 伸蒯/基、1,6~伸·、1,7一伸刷基、1,8—伸謝基、1 9- . 2,9^^2 ίο^ΙΤ 伸㈣。 ，11_伸荆基、2，J2- 刎基、3, 4-伸蒯基、3, 5一伸蒯基、3, 6_伸·、3， ,j基、3, UM淺基、3, u—伸测基、3, 12-伸荆基、4, 5— 伸蒯基、4, 6-伸劍基、4, u—伸荆基、4, 12-伸刷基、5,6_ 伸«基'5, 1卜伸《基、5, 12-伸劍基、6, 12一伸蒯基、4 4"卞 伸聯二苯基（4, 4"-p_terphenylene)、丨，丨，_伸聯蔡基、 9,9’-伸聯蒽基、1，2_伸菲基、1，3_伸菲基、1，4_伸菲基、 1，5~伸菲基、1，6~伸菲基、1，7-伸菲基、1，8-伸菲基、 伸菲基、1，10_伸菲基、2, 3-伸菲基、2, 4-伸菲基、2,卜 伸菲基、2,6-伸菲基、2,7_伸菲基、2,9_伸菲基、21〇_ 伸菲基、3, 4一伸菲基、3, 5_伸菲基、3, 6_伸菲基、3, 9、伸 菲基、3, 10-伸菲基、4, 5-伸菲基、4, 9-伸菲基、4, 1〇__伸 菲基、9, 10-伸菲基、l 2_伸$基、u 3_伸花基、i，扣伸祐 基、1’ 5-伸芘基、丨，6_伸芘基、丨，7_伸芘基、丨，8〜伸芘基、 95143 10 201204807 1，9-伸芘基、1，1 〇-伸芘基、2, 4_伸芘基、2, 5_伸芘基、2, 7一 伸芘基、4, 5-伸芘基、4, 9-伸芘基、4, 10-伸芘基、1，2-伸花基、1，3-伸茈基、1,4-伸茈基、1，5_伸茈基、1，6-伸 茈基、1，7-伸茈基、1，8-伸茈基、1，9-伸茈基、1, 10-伸茈 基、Ml-伸茈基、1,12-伸茈基、2, 3-伸茈基、2, 4-伸茈 基、2, 5-伸茈基、2, 8-伸茈基、2, 9-伸茈基、2, 10-伸茈基、 2, 1卜伸茈基、3, 4-伸茈基、3, 9_伸茈基、3, 1〇_伸茈基、 2, 2-伸金剛烷基、2, 4-伸比啶基、3, 4-伸吼啶基、3, 5-伸 °比啶基、2, 6-伸吼啶基、2, 5-伸吼啶基、2, 3-伸°比啶基、 2, 3-伸《比畊基、2, 5-伸吼畊基、2, 6-伸吼畊基、2, 4-伸三 畊基、2, 3-伸呋喃基、2, 4-伸呋喃基、2, 5-伸呋喃基、3, 4-伸11夫味基、2, 3-伸β塞吩基（2, 3-thiophenylene)、2, 4-伸0塞 吩基、2, 5-伸嗟吩基、3, 4-伸喔吩基、2, 3-伸栖吩基 (2, 3-selenophenylene)、2, 4-伸硒吩基、2, 5-伸硒吩基、 3, 4-伸砸吩基、2, 5-伸（1，3, 4-噚二唑）基、2, 5-伸（1, 3, 4-噻二唑）基、2, 5-伸（1，3, 4-硒二唑）基、2, 3-伸喹啉基、2, 4-伸喹啉基、2, 5-伸喹啉基、2, 6-伸喹琳基、2, 7-伸喹啉基、 2, 8-伸喹琳基、3, 4-伸喹琳基、3, 5-伸喹琳基、3, 6-伸喹 啉基、3, 7-伸喹啉基、3, 8-伸喹啉基、4, 5-伸喹啉基、4, 6-伸喹琳基、4, 7-伸喹琳基、4, 8-伸喹淋基、5, 6-伸喹啉基、 5, 7-伸喹啉基、5, 8-伸喹啉基、6, 7-伸喹啉基、6, 8-伸喹 啉基、7, 8-伸喹啉基、2, 3-伸喹噚啉基、2, 5-伸喹噚啉基、 2, 6-伸喹噚啉基、2, 7-伸喹噚啉基、2, 8-伸喹噚啉基、5, 6_ 伸喹噚啉基、5, 7-伸喹噚啉基、5, 8-伸喹曙啉基、6, 7-伸 11 95143 201204807 ㈣琳基、2, 3-物吩并[3, 4娘啡）基、2, 5_物吩 并[3, 并）基、2, 7-伸（嗟吩并[3, 4_b]n比啡）基、& 伸（嗟吩并[3,4-b]吼哄)基、2,3—伸（石西吩并[以姊比啡） 基、2, 5-伸（砸吩并[3, 4#比0井）基、2, 7一伸（砸吩并心一^ 謂）基、5,7-伸（砸吩并[3,4_b]轉）基、2,7_伸（苯并 噻唾）基、2, 6-伸（苯并[d]D塞唾）基、2, 5_伸（苯并⑷售哇） 基、2, 4-伸（苯并⑷嗟唾）基、4, 7_伸（苯并[仆塞唾）基、 5, , 6,7Ht(^*[d]^^)A . 5,6- 伸（苯并[d]°塞唾）基、4, 6-伸（苯并[d]嗟嗤）基、4, 5一伸（苯 并[d]嗟唾）基、 基、2, 5-伸（1，1〇-。非琳）基、2, 6_伸〇, 1〇_啡琳）基、2, 了一 伸（1，10-啡琳）基、2, 8_伸（1，1〇—啡琳）基、2, 9_伸（1，’ι〇_ 啡琳）基3, 4-伸（1，ι〇_啡琳;)基、3, 5_伸（1，1〇_啡琳）基、 3’ 6-伸（1，10-啡琳）基、3, 7__伸（1，1〇一啡琳）基、& 8_伸 (1，10-啡琳）基、4, 5-伸（1，10-啡琳）基、4, η申（1，1〇一啡 琳）基、4,7-伸啡琳）基、5,6^(1，1(Μμ)^99_ 二甲基-1，2-伸第基、9, 9一二甲基义3_伸第基、9, 9二曱 基-1，4-伸第基、9, 9_二曱基5_伸第基、9, 9二甲基 •1，6-伸第基、9, 9-二甲基-1，7-伸第基、9, 9_二曱基_f，8_ 伸第基、9, 9-二甲基—2, 3一伸第基、9, 9_二甲基' 4_伸第 基、9, 9-二曱基一2, 5_伸苐基、9, 9_二甲基_2, 6_伸第基、 9, 9-二曱基-2’ 7-伸第基、9, 9—二曱基_3, 4_伸g基、9,卜 二曱基-3, 5-伸第基、9, 9一二曱基一3, 6一伸隸、9 9二 基-4’ 5-伸第基、9’ 9_二乙基' 2_伸g基、9, 9_丄乙基 95143 12 201204807 _1，3-伸第基、9，9_二乙基_1，4-伸第基、9，9_二乙基-1，5_ 伸苐基、9，9_二乙基_1，6 -伸苐基、9，9-二乙基-1，7 -伸苐 基、9, 9-二乙基-1，8-伸苐基、9, 9-二乙基-2, 3-伸»基、 9，9_二乙基_2，4_伸苐基、9，9-二乙基_2，5_伸苐基、9，9_ 二乙基_2，6_伸第基、9，9_二乙基_2，7_伸第基、9，9_二乙 基_3，4_伸苐基、9，9_二乙基_3，5_伸苐基、9，9_二乙基 _3，6_伸苐基、9，9_二乙基_4，5_伸苐基、9，9_二苯基_1，2_ 伸荞基、9, 9-二苯基-1，3-伸苐基、9, 9-二苯基-1,4-伸苐 基、9，9-二苯基-1，5_伸苐基、9，9_二苯基-1，6_伸第基、 9, 9-二苯基-1，7-伸苐基、9, 9-二苯基-1，8-伸苐基、9, 9-二苯基-2, 3-伸第基、9, 9-二苯基-2, 4-伸苐基、9, 9-二苯 基-2, 5-伸苐基、9, 9-二苯基-2, 6-伸第基、9, 9-二苯基 -2，7-伸苐基、9，9-二苯基_3，4-伸苐基、9，9_二苯基_3，5_ 伸苐基、9, 9-二苯基-3, 6-伸苐基、9, 9-二苯基-4, 5-伸苐 基、9, 9-二環己基-1, 2-伸第基、9, 9-二環己基-1, 3-伸苐 基、9，9-二環己基-1,4-伸苐基、9, 9-二環己基-1,5-伸第 基、9, 9-二環己基-1，6-伸苐基、9, 9-二環己基-1,7-伸荞 基、9, 9-二環己基-1，8-伸苐基、9, 9-二環己基-2, 3-伸苐 基、9，9-二環己基-2, 4_伸苐基、9，9_二環己基_2，5-伸苐 基、9, 9-二環己基-2, 6-伸苐基、9, 9-二環己基-2, 7-伸荞 基、9, 9-二環己基-3, 4-伸苐基、9, 9-二環己基-3, 5-伸荞 基、9, 9-二環己基-3, 6-伸苐基、9, 9-二環己基-4, 5-伸葬 基，或，選自下列結構之二價基團，但不限於此： 13 95143 201204807Ri3 to Rig independently represent argon, (C1-C60) alkyl, (C3-C60) cycloalkyl, (C6-C60) aryl, (c2_c6〇) heteroaryl containing one or more heteroatoms (this The hetero atom is selected from the group consisting of N, 0, S, Si and Se), (C1-C60) alkoxy, (C1-C60)alkylthio, (C6-C60)aryloxy, (C6_C6〇)aryl a thio group, a mono- or di-(C1-C60)alkylamino group, a mono- or di-(C6_C6〇;) arylamino group, a (C6-C30) aryl (C1-C30) alkylamino group, Tris (cl_C3〇;) alkyl fluorenyl, di(C1-C30)alkyl (C6-C30) aryl fluorenyl, or tris(C6-C30)aryl fluorenyl; or heart with Ri4, Ri6 and Rn, And Ri8 is bonded to the heart via a (C3-C60)alkyl or (C3-C60) alkenyl group with or without a fused ring to form an aliphatic ring, or a monocyclic or polycyclic aromatic ring; a, b and c are independent The ground represents an integer from 1 to 4; d represents an integer from 1 to 3; and m and η independently represent an integer from 1 to 4. [Embodiment] In the present invention, an alkyl group, a "alkoxy" and other substituents including "alkyl" knives include straight chain or branched chain. The term "aryl" as used herein, is derived from an aromatic group by the removal of an organic radical derived from a hydrogen atom. Each ring includes a monocyclic or copper ring system, including 4 to 7, preferably 5 to 6 ring atoms. Specific examples of aryl groups include phenyl, naphthyl, biphenyl, anthracenyl, fluorene 7 95143 201204807, Indenyl, phenanthryl, triphenylenyl, fluorenyl, aryl, chrysenyl, naphthacenyl and fluoranthenyl, but not limited thereto . The term "heteroaryl" as used herein refers to a hetero atom selected from the group consisting of N, 0, S, P, Si and Se which is an aromatic ring skeleton atom, and as a residual aromatic ring skeleton atom. An aryl group of a carbon atom. The heteroaryl group may be a 5- or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group fused to one or more benzene rings, and may be partially saturated. The heteroaryl group may include a divalent aryl group on which a hetero atom is oxidized or quaternized to form an N-oxide, a quaternary salt or the like. Specific examples of heteroaryl groups include monocyclic heteroaryl groups such as e-furanyl, porphinyl, π-pyryinyl, 0-saltyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl , isoxazolyl, oxazolyl, oxadiazolyl, tridecyl, tetra-negative, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl, pyrimidinyl, hydrazine; Cycloheteroaryl such as benzofuranyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, Isoindolyl, fluorenyl, carbazolyl, benzothiadiazolyl, quinolyl, isolinyl, cinnolinyl, wow salicyl, hydrazine, 啥曙琳基, ° Cardinal, morphine and benzodioxolyl; and corresponding N-oxides (such as π than N-oxide, 喧 N-oxide), and its quaternary salts; But it is not limited to this. The substituents described herein containing "(C1-C60)alkyl" moieties may contain from 1 to 60 carbon atoms, from 1 to 20 carbon atoms' or from 1 to 1 carbon atoms. A substituent comprising a "(C6-C60) aryl" moiety may comprise from 6 to 6 〇 8 95143 201204807 carbon atoms, from 6 to 20 carbon atoms, or from 6 to one carbon atom. The (C3-C6G)heteroaryl group, a part of the substituent, may contain 3 to 60 carbon atoms = 4 to 20 carbon atoms' or 4 to 12 carbon atoms. Included, the substituent of the '(C3_C60) ring, group" moiety may contain 3 to (10) rhymes, 3 to 2 〇 = carbon atoms, or 3 to 7 carbon atoms. A substituent comprising a "(C2_(10) group or fast radical" moiety may comprise from 2 to 6 carbon atoms, from 2 to 2 carbon atoms 'or from 2 to 1 carbon atoms. / represents 1,2-extension Phenyl, l 3 —phenyl, u 4 —phenyl, ^ 2 — anthranyl, 1,3-naphthyl, 1>4-naphthyl, anthracene, phenyl, 16^, naphthyl, 1,7 -Naphthyl, !,8_Naphthyl, 2,3_Streptyl, & 6_Anthranyl, 2,7-Extenylene, u 2_Extenient, i,3_ Base, * an onion base, 1' extension base, 1,6-extension base, I 7 - extension base, u 8_ extension base: two extension base, 丨, 10 one extension base, 2, 3-extension base, 2, 6-extension base, 2 plant onion base, 2, 9-extension base, 2, 1 〇-extension base, 9, j extension | & , 3,-Extenobiphenyl, 4, 4,-Extended biphenyl, ! will be - lean η. 丨, t extension and extension 丞 U, 2-tnhenylenyl), 1,3-extension Stretching three joints and stretching three stupid bases,... Stretching two: 'Two extensions and two bases, U0-extension and extension three stupid bases, u Bu extensions and extensions three 1 '12-extension joints triphenyl, 2, 3_ extensions and extensions Base, 2, ^ base, 2, 7-extension, triphenyl, 2, 丨 伸 联 联 三 三 、 1, 1, 2 fluor 妇 第 ( ( 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 5-extended propylene disulfide group, propylene diacetate IS group, 1,7-extended alkadiene g group, U8 ^ '6~Extension group, 1,9-extension two diene burial group , uh 申丙二二合合合合2, 3- 95143 9 201204807 201204807 'Sparse 2, 9- • 归合3, 9- 稀合合::2二烯二!基,2'4'伸丙Diene g group, 2,5-extended propylene diradical, 2,8-extended propylidene group 1-3, 2,1 〇1 propylene, diazide, 3,4-丙丙基,3,7-Extended alkadienediyl, 3,8-extension-propylene dibasic-based propylene-dithiocarbamate, 3,1M Shen-Pro## 7 η ^ ' 口弗U, 8-Extended adiene < 二稀合$基,Μ,丙二稀合基基,"_伸丙:She, U韵,U部^伸蒯/基,1,6~伸·,1, 7 one stretch brush base, 1, 8 - stretch Xie Ji, 1 9- . 2, 9 ^ ^ 2 ίο ^ ΙΤ stretch (four). , 11_ stretching, 2, J2-mercapto, 3, 4-extension, 3, 5, exfoliation, 3, 6_extension, 3, j, 3, UM shallow, 3, U—extension base, 3, 12-extension base, 4, 5—extension base, 4, 6-extension base, 4, u-extension base, 4, 12-stretch base, 5,6_ extension «基'5, 1 卜伸 "基,5,12-伸剑基,6,12一伸蒯基,4 4"卞伸联二苯(4, 4"-p_terphenylene), 丨, 丨, _联蔡基, 9,9'-Extension 蒽基,1,2_伸菲基,1,3_伸菲基,1,4_伸菲基, 1,5~伸菲基,1,6~ Phenanthrene, 1,7-exphenanthrene, 1,8-exetylene, phenanthrene, 1,10- phenanthrenyl, 2, 3-defending phenanthryl, 2, 4-defending phenanthryl, 2,卜伸菲基,2,6-延菲基,2,7_伸菲基,2,9_伸菲基,21〇_ 延菲基,3,4一伸菲基,3,5_伸菲基, 3, 6_ phenanthrene, 3, 9, phenanthrenyl, 3, 10-extended phenanthryl, 4, 5-exetylene, 4, 9-ephthyl, 4, 1〇__ , 9, 10 - phenanthrene, l 2_ stretch $ base, u 3_ stretch flower base, i, buckle stretch base, 1' 5-extension base, 丨, 6_伸芘 base, 丨, 7_ stretch芘基,丨,8~伸芘基,95143 10 201204807 1 9-extension base, 1,1 〇-extension base, 2, 4_extension base, 2, 5_extension base, 2, 7-extension base, 4, 5-extension base, 4, 9- Extensible base, 4, 10-extension base, 1,2-extension base, 1,3-extension base, 1,4-extension base, 1,5_extension base, 1,6-extension Base, 1,7-extension base, 1,8-extension base, 1,9-extension base, 1, 10-extension base, Ml-extension base, 1,12-extension base, 2, 3-extension base, 2, 4-extension base, 2, 5-extension base, 2, 8-extension base, 2, 9-extension base, 2, 10-extension base, 2, 1 b Stretching base, 3, 4-extension base, 3, 9_extension base, 3, 1〇_extension base, 2, 2-extended adamantyl, 2, 4-extended pyridyl, 3, 4 - anthranilyl, 3, 5-extended pyridine, 2,6-exetidinyl, 2,5-exetidinyl, 2,3-extended ratio pyridine, 2, 3-extended Specific tillage, 2, 5-extension, 2, 6-extension, 2, 4-extension, 2, 3-furan, 2, 4-furfuryl, 2, 5- a furanyl group, a 3,4-extended 11-glycosyl group, a 2,3-thiophenylene group, a 2,4-extended 0-thiophene group, a 2, 5-anthracene group, 3, 4-extended phenyl, 2, 3-selenophenylene, 2, 4-strenyl 2, 5-extension seleno, 3, 4-extended phenyl, 2, 5-extended (1,3, 4-oxadiazole), 2, 5-extended (1, 3, 4-thiadi Azyl), 2, 5-extended (1,3,4-selenodiazole), 2,3-extended quinolinyl, 2,4-extended quinolinyl, 2,5-quinolinolyl, 2 , 6-extended quinolinyl, 2,7-extended quinolinyl, 2, 8-quinazolinyl, 3, 4-quinolinyl, 3, 5-quinazolinyl, 3,6-quinoquine Lolinyl, 3,7-extended quinolyl, 3,8-extended quinolinyl, 4,5-extended quinolinyl, 4,6-extended quinolinyl, 4,7-extended quinalyl, 4, 8-retinolinyl, 5,6-extended quinolinyl, 5,7-extended quinolinyl, 5, 8-extended quinolinyl, 6,7-extended quinolinyl, 6, 8-extended quinoline , 7, 8-extended quinolinyl, 2, 3-quinoxalinyl, 2, 5-quinoxalinyl, 2,6-extended quinoxalinyl, 2,7-extended quinoxaline , 2, 8-extended quinoxalinyl, 5, 6-extended quinoxalinyl, 5,7-extended quinoxalinyl, 5, 8-quinoquinolinyl, 6, 7-extension 11 95143 201204807 (d) Base, 2, 3-mero[3,4-female), 2,5-e-[3,-), 2,7-extension (嗟,[3,4_b]n than morphine) Base, & extension (嗟, [3,4-b]吼哄), 2,3 - extension (Shishen [[姊比啡]) 2, 5-extension (砸, [3, 4# is 0 well) base, 2, 7 one extension (砸 并 一 ^ ^ )) base, 5, 7- extension (砸, [3, 4_b] turn ), 2,7-extended (benzothiasinyl), 2,6-extended (benzo[d]D-sodium), 2,5-extended (benzo(4) for sale), 2, 4 -extension (benzo(4)pyrene), 4,7_extension (benzo[,], 5, 6,6Ht(^*[d]^^)A. 5,6-extension (benzene And [d] ° 塞 ) base, 4, 6-extension (benzo[d] fluorene), 4, 5-extension (benzo[d] 嗟 )), base, 2, 5-extension (1 , 1〇-. Non-琳) base, 2, 6_ stretch, 1〇_啡琳) base, 2, a stretch (1,10-morphine) base, 2, 8_ stretch (1,1〇-morphine) base, 2, 9_Extension (1, 'ι〇_ 琳琳) base 3, 4-extension (1, ι〇_啡琳;) base, 3, 5_ extension (1,1〇_啡琳) base, 3 '6-extension (1,10-morphine) base, 3, 7__extension (1,1 〇 啡 啡 )) base, & 8_extension (1,10- morphine) base, 4, 5-extension (1,10-morphine) group, 4, η申(1,1〇一啡琳), 4,7-extension, base, 5,6^(1,1(Μμ)^99_ dimethyl Base-1,2-extension base, 9,9-dimethylene-3_extension, 9,9-didecyl-1,4-extension, 9,9-didecyl 5-_ 1,9,9-dimethyl-1,6-extension, 9,9-dimethyl-1,7-extension, 9,9-didecyl-f,8_extension, 9, 9-Dimethyl- 2,3-extension, 9,9-dimethyl '4-extension, 9,9-diindenyl-2, 5-extension, 9,9-dimethyl _2, 6_Extension, 9, 9-dimercapto-2' 7-extension, 9, 9-diyl _3, 4_extension g, 9, bisindyl-3, 5-extension base, 9, 9-two-mercapto- 3, 6-extension, 9 9-diyl-4' 5-extension, 9' 9-diethyl' 2_ 9,9_丄ethyl 95143 12 201204807 _1,3-extension, 9,9_diethyl-1,4-extension, 9,9-diethyl-1,5_ 9,9-diethyl_1,6-extended fluorenyl, 9,9-diethyl-1,7-extended fluorenyl, 9,9-diethyl-1,8-extension, 9, 9-Diethyl-2,3-extension», 9,9-diethyl-2,4_extension, 9,9-diethyl-2,5-extension, 9,9_ Ethyl 2,6-extension, 9,9-diethyl-2,7-extension, 9,9-diethyl_3,4_extension, 9,9-diethyl _3,5_extension base, 9,9_diethyl_3,6_extension base, 9,9_diethyl_4,5_extension base, 9,9_diphenyl_1 , 2_ hydrazino, 9, 9-diphenyl-1,3-decyl, 9,9-diphenyl-1,4-anthracene, 9,9-diphenyl-1,5_ Retinoic acid, 9,9-diphenyl-1,6-extension, 9,9-diphenyl-1,7-extension, 9,9-diphenyl-1,8-extension , 9,9-diphenyl-2,3-extended, 9,9-diphenyl-2,4-extended, 9,9-diphenyl-2, 5-decyl, 9, 9-diphenyl-2,6-extension, 9,9-diphenyl-2,7-extension, 9,9-diphenyl-3,4-decyl, 9, 9_diphenyl_3,5_ 9,9-diphenyl-3,6-extended fluorenyl, 9,9-diphenyl-4, 5-extended fluorenyl, 9,9-dicyclohexyl-1, 2-extension, 9 , 9-dicyclohexyl-1,3-extended fluorenyl, 9,9-dicyclohexyl-1,4-anthracenyl, 9,9-dicyclohexyl-1,5-extension, 9,9 -dicyclohexyl-1,6-extension, 9,9-dicyclohexyl-1,7-extension, 9,9-dicyclohexyl-1,8-extension, 9,9-di Cyclohexyl-2,3-extended fluorenyl, 9,9-dicyclohexyl-2,4_extension, 9,9-dicyclohexyl-2,5-extenylene, 9,9-dicyclohexyl -2,6-extended, 9,9-dicyclohexyl-2,7-extension, 9,9-dicyclohexyl-3,4-extended, 9,9-dicyclohexyl-3 , 5-extended fluorenyl, 9,9-dicyclohexyl-3,6-extended fluorenyl, 9,9-dicyclohexyl-4, 5-carving group, or a divalent group selected from the following structures , but not limited to: 13 95143 201204807

更具體地，γ為選自下列結構之二價基團。 TAR1More specifically, γ is a divalent group selected from the following structures. TAR1

TAR4 14 95143 201204807TAR4 14 95143 201204807

TAR8 TAR9 JAR10 TAR11 ·1· ·% ·<^>·孤· ：0 f TAR13 \J TAR« TAR1# TAR18TAR8 TAR9 JAR10 TAR11 ·1· ·% ·<^>·孤·:0 f TAR13 \J TAR« TAR1# TAR18

TARU ^λ3"* TAD1 THAI THA2 THA3 THM THA6 TAR19 TAR20 、办H m W W1 THA9 THA10 THA11 ΤΗΑβ THAT 〜▲· 冬 THA12 THA13 THA14 I I I ·容·姆·册，· * ** THA18 THA20 ^21 ΤΗΑ1β ΤΗΑ16 ΤΗΑ17 ΤΗΑ18 J[Hr^ 讎細酬 娜 讎 —- ΤΥ1 7X2 15 95143 201204807TARU ^λ3"* TAD1 THAI THA2 THA3 THM THA6 TAR19 TAR20, H m W W1 THA9 THA10 THA11 ΤΗΑβ THAT ~▲· Winter THA12 THA13 THA14 III · Rong·M······ ** THA18 THA20 ^21 ΤΗΑ1β ΤΗΑ16 ΤΗΑ17 ΤΗΑ18 J[Hr^ 雠 fine reward 雠 雠 - 1 7X2 15 95143 201204807

(Ri).(Ri).

係選自下列結構，但不限 於此： 16 95143 201204807It is selected from the following structures, but is not limited to: 16 95143 201204807

結構structure

17 95143 20120480717 95143 201204807

本發明之有機電場發光化合物可依據流程圖1至4製 備。 流程圖1The organic electroluminescent compound of the present invention can be prepared according to the schemes 1 to 4. Flow chart 1

18 95143 201204807 流程圖218 95143 201204807 Flowchart 2

其中 尺1至85、乂、丫、3、13、（：與（1之定義與化學式1與2 之定義相同。 係提供一種有機電場發光裝置，其包含第一電極；第 二電極；以及一層或多層置於該第一電極與第二電極之間 之有機層，其中該有機層包含一種或多種由化學式1或2 表示之有機電場發光化合物。 該有機層包含電場發光層，其包括一種或多種主體， 並使用一種或多種化學式1或2之有機電場發光化合物作 為摻雜劑。 用於本發明有機電場發光裝置之主體並無特別限制， 但可選自由化學式3或4表示之化合物。 19 95143 201204807 [化學式3] (An)e-Li-(Ar2)f [化學式4] (Ar3)g*~L2_( Ar4)h 其中Wherein the scales 1 to 85, 乂, 丫, 3, 13, (: and (1 are the same as defined in Chemical Formulas 1 and 2) provide an organic electric field illuminating device comprising a first electrode; a second electrode; and a layer Or an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compounds represented by Chemical Formula 1 or 2. The organic layer comprises an electric field luminescent layer comprising one or A plurality of hosts are used, and one or more organic electroluminescent compounds of the chemical formula 1 or 2 are used as a dopant. The main body of the organic electroluminescence device of the present invention is not particularly limited, but a compound represented by Chemical Formula 3 or 4 may be selected. 95143 201204807 [An)e-Li-(Ar2)f [Chemical Formula 4] (Ar3)g*~L2_(Ar4)h

Li表示（C6-C60)伸芳基或（C4-C60)雜伸芳基； L2表示伸蒽基；Li represents (C6-C60) an aryl group or a (C4-C60) heteroaryl group; L2 represents a thiol group;

An至Ar4獨立地選自氫、氘、（C1-C60)烷基、（C卜C6〇) 烷氧基、齒素、（C4-C60)雜芳基、（C5-C60)環烷基，以及 (C6-C60)芳基，且An至An之該環烷基、芳基或雜芳基可 進一步經一個或多個選自下列所組成群組之取代基取代： 具有或不具一個或多個選自經或未經鹵素取代之 烷基、（C1-C60)烷氧基、（C3-C60)環烷基、鹵素、氰基、 三（C1-C60)烷基矽基、二（C1-C60)烷基（C6-C60)芳基石夕 基，與三（C6-C60)芳基矽基之取代基的（C6-C60)芳基或 (C4-C60)雜芳基；經或未經_素取代之（c卜C60)烷基； (C1-C60)烷氧基；（C3-C60)環烷基；鹵素；氰基；三（C1_C6(〇 烷基矽基；二（C1-C60)烷基（C6-C60)芳基矽基；以及三 (C6-C60)芳基矽基；以及 e、f、g與h獨立地表示〇至4之整數。 化學式3與4表示之主體可以下列化學式5至7化合 物作為範例。 20 95143 201204807 化學式5An to Ar4 are independently selected from the group consisting of hydrogen, hydrazine, (C1-C60) alkyl, (C-C6〇) alkoxy, dentate, (C4-C60)heteroaryl, (C5-C60)cycloalkyl, And (C6-C60) aryl, and the cycloalkyl, aryl or heteroaryl group of An to An may be further substituted with one or more substituents selected from the group consisting of: with or without one or more One selected from alkyl substituted with or without halogen, (C1-C60) alkoxy, (C3-C60)cycloalkyl, halogen, cyano, tri(C1-C60)alkyldecyl, di(C1 -C60) alkyl (C6-C60) aryl fluorenyl, (C6-C60) aryl or (C4-C60) heteroaryl with a substituent of a tris(C6-C60) aryl fluorenyl group; Substituted (c-C60)alkyl; (C1-C60)alkoxy; (C3-C60)cycloalkyl; halogen; cyano; tri(C1_C6(decylalkyl); C60) an alkyl (C6-C60) aryl fluorenyl group; and a tri(C6-C60) aryl fluorenyl group; and e, f, g and h independently represent an integer of 〇 to 4. The main formulas represented by Chemical Formulas 3 and 4 The following compounds of the chemical formulas 5 to 7 can be exemplified. 20 95143 201204807 Chemical Formula 5

(ce-cL^r立地表示H (ei'e6G)錄、齒素、 土、（C4~C60)雜芳基、含有一個或多個雜原子 元雜環燒基（該雜原子選自心〇與幻、或（c3_c6〇) 環烧基以及该R21與R22之該芳基或雜芳基可進一步經一 個或夕個選自下列所組成群組之取代基取代：（n-C60)烧 基、函（C1-C60)烷基、（C1-C60)烷氧基、（C3-C60)環烷基、 (C6-C60)芳基、（C4-C6〇)雜芳基、齒素、氰基、三（C1_C60) 烧基石夕基、二（C1-C60)烷基（C6-C60)芳基矽基，以及三 (C6-C60)芳基石夕基； R23至R26獨立地表示氫、氘、（C1_C60)烷基、（C1_C60) 烷氧基、齒素、（C4-C60)雜芳基、（C5-C60)環烷基或（C6-C60) 21 95143 201204807 d MitlU至r1D6之該雜絲、環烧基或絲可進一 步、’生個或多個選自下列所組成群組之取代基取代 :經或 t素取代之（C卜⑽）燒基、（._烧氧基、（C3 -C60) 二甘'^'自素、氰基、三（C卜C60)烧基石夕基、二（C1-C60) 芳基_基’與三（C6-C6G)芳基石夕基；(ce-cL^r stands for H (ei'e6G), dentate, earth, (C4~C60) heteroaryl, containing one or more heteroatoms heterocyclic alkyl groups (the hetero atom is selected from the group of palpitations) And the aryl or (c3_c6〇) cycloalkyl group and the aryl or heteroaryl group of the R21 and R22 may be further substituted with one or a substituent selected from the group consisting of: (n-C60) alkyl , (C1-C60)alkyl, (C1-C60)alkoxy, (C3-C60)cycloalkyl, (C6-C60)aryl, (C4-C6〇)heteroaryl, dentate, cyanide a base, a tris(C1_C60) alkyl group, a bis(C1-C60)alkyl (C6-C60) aryl fluorenyl group, and a tris(C6-C60) aryl fluorenyl group; R23 to R26 independently represent hydrogen and hydrazine; , (C1_C60)alkyl, (C1_C60) alkoxy, dentate, (C4-C60)heteroaryl, (C5-C60)cycloalkyl or (C6-C60) 21 95143 201204807 d MitlU to r1D6 The silk, cycloalkyl or silk may be further substituted with one or more substituents selected from the group consisting of: (C (10)) alkyl, (. C3 -C60) Di Gan '^' self-sugar, cyano, tri-(C-C60)-based basestone, di(C1-C60) aryl-based 'and three (C6-C6G) aryl stone base;

Ln與L13獨立地表示化學鍵、或具有或不具—個或多 、、自（Cl C60)燒基、（cl_C6〇)烧氧基、（C6 c⑹芳基、 C4 C6〇)雜芳基與南素之（C6-C60)伸芳基。 (C4-C6G)雜芳基f立地表不選自1"列結構之芳基、或表示Ln and L13 independently represent a chemical bond, or with or without - or more, from (Cl C60) alkyl, (cl_C6〇) alkoxy, (C6 c(6) aryl, C4 C6〇) heteroaryl and sulfa (C6-C60) extended aryl. (C4-C6G) Heteroaryl f is not selected from the aryl group of 1"column structure, or

Arn與ArI2之該芳基或雜芳基可進一步經一個或多個 選自（C1⑽）絲、（(：1~⑽）烧氧基、（C6-C6G)芳基與 (C4-C60)雜芳基之取代基取代；The aryl or heteroaryl group of Arn and ArI2 may further be selected from one or more selected from the group consisting of (C1(10)) silk, ((:1~(10)) alkoxy, (C6-C6G) aryl and (C4-C60) Substituent substitution of an aryl group;

Ll2表不（C6-C60)伸芳基、（C4-C60)雜伸芳基、或 ^3βνχ^3βLl2 indicates not (C6-C60) aryl, (C4-C60) heteroaryl, or ^3βνχ^3β

以及U之該伸芳基或雜伸芳基可更進一 步經一個或多個選自（…⑽）絲、（C1-⑽）烧氧基、 (C6-C6G)芳基、（(：4___基與㈣之取代基取代，· 95143 22 201204807 心至R34獨立地表示氫、氘、（cl_C6〇)烷基或（C6_C6〇) 芳基，或1^至R34可經由具有或不具稠合環之（C3_C6〇)伸 烧基或（C3-C60)伸埽基與相鄰之取代基聯結，以形成脂肪 環、或單環或多環之芳香環；以及 r35至r38獨立地表示氫、氘、（cn_c60)烷基、（cl_C6〇) 烷氧基、（C6-C60)芳基、（C4-C6O)雜芳基或_素，或R35 至R38可經由具有或不具稠合環之（C3_C6〇)伸烷基或 (C3-C60)伸烯基與相鄰之取代基聯結，以形成脂肪環、或 單環或多環之芳香環。 該電場發光層係指產生電場發光之層，可為單層或由 二層或多層層合之多層。當主體_摻_混合物依據本發明 組成使用時，已確認該電場發光主體對於發光效率有大幅 增進。 推雜濃度可為〇· 5至l〇wt%。當與現今其他主體材料 比較時，本發明之電場發光主體可提供絕佳之電洞與電子 導，度’以及非常良好之穩定性’與顯著增進之發光效率 與才呆作命。 發光當選用由化學式3至7表示之化合物作為電場 體時，可明顯補償本發明由化學式1或2表示之有 機電場發光化合物之電性缺點。f 該有機電場發光裝置可包含化學式丨或 :ί:合物，且可包含-種或多種選自芳基胺二 化二物或苯乙縣胺（styrylamine)化合物所組成群組之 " 孩芳基胺或笨乙烯基合物之範例包括具下列 95143 23 201204807 化學式8之化合物，但不受限於此。 化學式8And the extended aryl or heteroaryl group of U may be further passed through one or more selected from (...(10)) silk, (C1-(10)) alkoxy, (C6-C6G) aryl, ((:4___ Substituted with a substituent of (d), · 95143 22 201204807 Heart to R34 independently represents hydrogen, deuterium, (cl_C6〇)alkyl or (C6_C6〇)aryl, or 1^ to R34 may be via or without a fused ring (C3_C6〇) a stretching group or a (C3-C60) stretching group is bonded to an adjacent substituent to form an aliphatic ring, or a monocyclic or polycyclic aromatic ring; and r35 to r38 independently represent hydrogen, deuterium, (cn_c60)alkyl, (cl_C6〇)alkoxy, (C6-C60)aryl, (C4-C6O)heteroaryl or _, or R35 to R38 via or without a fused ring (C3_C6〇 An alkyl group or a (C3-C60) extended alkenyl group is bonded to an adjacent substituent to form an aliphatic ring, or a monocyclic or polycyclic aromatic ring. The electric field luminescent layer refers to a layer that generates an electric field luminescence, which may be A single layer or a plurality of layers laminated by two or more layers. When the host-doped mixture is used in accordance with the composition of the present invention, it has been confirmed that the electric field illuminating body has a large increase in luminous efficiency. The concentration can be from 至·5 to 〇wt%. The electroluminescent body of the present invention provides excellent hole and electron conductivity, degree 'and very good stability' and significant enhancement when compared with other host materials today. The luminous efficiency is in agreement with the luminescence. When the compound represented by Chemical Formulas 3 to 7 is selected as the electric field body, the electrical disadvantage of the organic electroluminescent compound represented by Chemical Formula 1 or 2 of the present invention can be significantly compensated. The illuminating device may comprise a chemical formula or a: ε: and may comprise one or more selected from the group consisting of an arylamine dimer or a styrylamine compound. Examples of the stupid vinyl compound include the following compounds of the formula 95143 23 201204807, but are not limited thereto.

其中among them

Ar31與Ar32獨立地表示（C1_C60)烷基、（C6_C6〇)芳基、 (C4-C6〇)雜芳基、（C6-C60)芳基胺基、（C1-C60)烷基胺基、 含一個或多個雜原子之5-至6-元雜環烧基（該雜原子選自 N、0與S)、或（C3-C60)環烧基，且Αηι與Ar32可經由具有 或不具稍合環之（C3-C60)伸烧基或（C3-C60)伸烯基與相鄰 取代基聯結，以形成脂肪環、或單環或多環之芳香環； 當k為1時，Ar33表示（C6-C60)芳基或（C4-C60)雜芳 基，或At*33為具有下列結構之取代基； R—Ar“ R92 R93 當k為2時，Ar”表示（C6-C60)伸芳基或（C4-C60)雜 伸芳基，或Ana為具有下列結構之取代基； R93 A1·34與Ar*35獨立地表示（C6-C60)伸芳基或（C4-C60)雜 伸芳基； !^至R93獨立地表示氫、（C1-C60)烷基或（C6-C60)芳 24 95143 201204807 基； P表示1至4之整數，q表示整數〇或1，Ar31 and Ar32 independently represent (C1_C60)alkyl, (C6_C6〇)aryl, (C4-C6〇)heteroaryl, (C6-C60)arylamino, (C1-C60)alkylamino, including a 5- to 6-membered heterocyclic group of one or more heteroatoms (the hetero atom is selected from N, 0 and S), or a (C3-C60) cycloalkyl group, and Αηι and Ar32 may be via or without The cyclo(C3-C60) extended alkyl group or (C3-C60) extended alkenyl group is bonded to an adjacent substituent to form an aliphatic ring, or a monocyclic or polycyclic aromatic ring; when k is 1, Ar33 represents (C6-C60) aryl or (C4-C60)heteroaryl, or At*33 is a substituent having the following structure; R-Ar" R92 R93 When k is 2, Ar" means (C6-C60) Aryl or (C4-C60) heteroaryl, or Ana is a substituent having the following structure; R93 A1·34 and Ar*35 independently represent (C6-C60) extended aryl or (C4-C60) heterosexual Aryl; !^ to R93 independently represent hydrogen, (C1-C60)alkyl or (C6-C60)aryl 24 95143 201204807; P represents an integer from 1 to 4, and q represents an integer 〇 or 1,

Ar3i與An2之該烷基、芳基、雜芳基、芳基胺基、烷 基胺基、環燒基或雜環烷基，或Ar33之該芳基、雜芳基、 伸芳基或雜伸芳基，或Ar34與Ans之該伸芳基與雜伸芳 基’或R⑼至Rm之該烷基或芳基，可更進一步經一個或多 個選自下列所組成群組之取代基取代：鹵素、（C1-C60)烷 基、（C6-C60)芳基、（C4-C60)雜芳基、含一個或多個雜原 子之5-至6-元雜環烷基（該雜原子選自卜〇與s)、（C3_C6〇) 環烷基、三（C1-C60)烷基矽基、二（C1_C60)烷基（C6_C6〇) 务基石夕基、二（C6-C60)芳基石夕基、金剛烧基、（C7—C60)雙 環烷基、（C2-C60)烯基、（C2-C60)炔基、氰基、（cl_C6〇) 烷基胺基、（C6-C60)芳基胺基、（C6-C60)芳（C1-C60)烷基、 (C6 C60)芳基氧基、（C1-C60)烧基氧基、（C6_C60)芳基辟 基、（C1-C60)烷基硫基、（C1-C60)烷氧基羰基、（C1—^ 烷基羰基、（C6-C60)芳基羰基、羧基、硝基與經基。 更具體地’該芳基胺化合物或苯乙烯基芳基胺 (styrylarylamine)化合物係以下列化合物作為示範作 受限於下列化合物。 95143 25 201204807The alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl group of Ar3i and An2, or the aryl, heteroaryl, aryl or heteroaryl group of Ar33 The aryl group, or the alkyl or aryl group of the aryl group and the heteroaryl group ' or R(9) to Rm of Ar34 and Ans, may be further substituted by one or more substituents selected from the group consisting of : halogen, (C1-C60)alkyl, (C6-C60)aryl, (C4-C60)heteroaryl, 5- to 6-membered heterocycloalkyl containing one or more heteroatoms (the hetero atom Selected from diterpenes and s), (C3_C6〇) cycloalkyl, tri(C1-C60)alkyldecyl, di(C1_C60)alkyl (C6_C6〇), fluorenyl, di(C6-C60) aryl夕基,Adamantyl, (C7-C60)bicycloalkyl, (C2-C60)alkenyl, (C2-C60)alkynyl, cyano, (cl_C6〇)alkylamino, (C6-C60) aryl Amino group, (C6-C60) aryl (C1-C60) alkyl, (C6 C60) aryloxy, (C1-C60) alkyloxy, (C6_C60) aryl, (C1-C60) Alkylthio, (C1-C60) alkoxycarbonyl, (C1-alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and thiol More specifically, the arylamine compound or the styryl arylamine compound is exemplified by the following compounds: 95143 25 201204807

26 95143 20120480726 95143 201204807

1族、第2族、第4週期與第5週期過渡金屬、鑭系金屬 與d-過渡金屬所組成群組之金屬。該有機層可包含電場發 光層與電荷產生層。 本發明係實現一種具有獨立發光模組之像素結構之 有機電場發光裝置，其包括一種有機電場發光裝置，其含 有化學式1或2之有機電場發光化合物作為次像素，以及 一種或多種包含一種或多種金屬化合物（選自Ir、Pt、Pd、 Rh、Re、〇s、Tl、Pb、Bi、In、Sn、Sb、Te、Au 與 Ag 所 組成群組）之次晝素（同時經平行圖樣化）。 此外，該有機層可形成發出白光之電場發光裝置，其 中該有機層同時復包含一層或多層發出藍光、紅光或綠光 之有機電場發光層。 在本發明之有機電場發光裝置+，可將選自硫族化合 物（chalcogenide)層、金屬鹵化物層與金屬氧化層之一層 (後文中稱之為"表面層"）設置於該電極對之一個或二個電 極之内表面上。更具體地，可將矽或鋁之金屬硫族化合物 27 95143 201204807 (包括氧化物）層設置於該電場發齡f層之陽極表面上， 而將金屬自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。可由此得到操作穩定性。該硫族化合物 可為如 ’ Si〇x(l^xs2)、Α1〇χ(1 各 5)、Si〇N、SiA剛 等。該金屬函化物可為如LiF、MgF2、CaF2、稀土金屬之氣 化物等。該金屬氧化物可為如Cs20、Li20、Mg0、Sr0、Ba0、 CaO 等。 在本發明之有機電場發光裝置中，較佳係將電子傳輸 化合物與還原性摻雜劑之混合區域，或電洞傳輸化合物與 氧化性摻雜劑之混合區域設於如是製造之電極對之至少一 表面上。在該情況下’由於電子傳輸化合物會被還原成陰 離子’便會幫助電子由混合區域注入與傳輸至電場發光介 質。此外，由於電洞傳輸化合物會被氧化成陽離子，便會 幫助電洞由混合區域注入與傳輸至電場發光介質。較佳之 氧化性摻雜劑包括各種路易士酸與接受者化合物 (acceptor compound)。較佳之還原性摻雜劑包括鹼金屬、 鹼金屬化合物、鹼土金屬、稀土金屬與其混合物。 有益效果 由於本發明之有機電場發光化合物具有良好之藍光 發光效率，以及絕佳之壽命性質，其可用於製造具有非常 良好之操作壽命之0LED裝置。 發明模式 本發明係就本發明之有機電場發光化合物、其製造流 程，以及使用該化合物之裝置之發光性質方面，作更清楚 28 95143 201204807 之描述。然而，下列範例僅用於說明，並非用於限制本發 明範疇。 「製備例1」化合物91之製備Metals of the group consisting of transition metals, lanthanide metals and d-transition metals of Group 1, Group 2, Period 4 and Period 5. The organic layer may comprise an electric field luminescent layer and a charge generating layer. The present invention is an organic electric field illuminating device having a pixel structure of an independent illuminating module, comprising an organic electric field illuminating device comprising an organic electroluminescent compound of Chemical Formula 1 or 2 as a sub-pixel, and one or more comprising one or more a metal compound (selected from the group consisting of Ir, Pt, Pd, Rh, Re, 〇s, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag) as a secondary protein (simultaneously parallelized) ). Further, the organic layer may form an electric field light-emitting device that emits white light, wherein the organic layer simultaneously includes one or more layers of an organic electric field light-emitting layer that emits blue light, red light, or green light. In the organic electric field light-emitting device of the present invention, a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as "surface layer") may be disposed on the electrode pair On the inner surface of one or both of the electrodes. More specifically, a layer of a metal chalcogenide 27 95143 201204807 (including an oxide) of ruthenium or aluminum may be disposed on the anode surface of the electric field age f layer, and a metal crystallization layer or a metal oxide layer may be disposed thereon. The electric field illuminates the cathode layer on the surface of the dielectric layer. Operational stability can thus be obtained. The chalcogenide may be, for example, 'Si〇x(l^xs2), Α1〇χ(1 each 5), Si〇N, SiA just, and the like. The metal complex may be a gas such as LiF, MgF2, CaF2, a rare earth metal or the like. The metal oxide may be, for example, Cs20, Li20, Mg0, Sr0, Ba0, CaO or the like. In the organic electric field light-emitting device of the present invention, preferably, 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 is provided in at least the electrode pair to be manufactured. On the surface. In this case, 'the electron transport compound will be reduced to an anion' will help the electrons to be injected and transported from the mixed region to the electric field illuminating medium. In addition, since the hole transporting compound is oxidized to a cation, the hole is injected and transported from the mixed region to the electric field illuminating medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. [Advantageous Effects] Since the organic electroluminescent compound of the present invention has good blue light-emitting efficiency and excellent life properties, it can be used to manufacture an OLED device having a very good operational life. Mode for Invention The present invention is described more clearly in terms of the organic electroluminescent compound of the present invention, the process for its production, and the luminescent properties of a device using the compound. 28 95143 201204807. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the invention. Preparation of Compound 91 of Preparation Example 1

化合物A之製備 將4-、;臭聯苯（30g，0. 12mol)加入單頸燒瓶中，於真空 下建立氬氣環境。加入四氫呋喃（THF)(500ml)，混合物於 -78°C攪拌1〇分鐘。加入n-BuLi(2. 5M溶於己烷中）（77ml， 0. 19mol)，將混合物於-78°C攪拌1小時又30分鐘。之後， 於-78°C加入三曱基硼酸酯（21. 9ml，0. 19mol)。混合物於 -78°C攪拌30分鐘後’再於室溫下攪拌4小時。待反應完 成後’使用蒸餾水與乙酸乙酯（EA)進行萃取。有機層係以 MgS〇4乾燥’並使用旋轉蒸發器移除溶劑。經管柱層析法， 使用己烷與EA作為沖提液，分離出純化合物A(21g, 84%)。 化合物B之製備 將卜溴-4-碘化苯（29g, 〇. l〇m〇l)、化合物A(21g，0. 10 29 95143 201204807 mol)與四（二苯基膦）纪（tetrakis(triphenylphosphine) Palladium)(5· 9g, 5. lmmol)加至二頸（二頸）燒瓶中。於加 入曱苯同時攪拌混合物後，加入2M K2C〇3(265ml, 0. 5mol) 與乙醇（265ml)。於l〇(Tc回流5小時後，當反應完成時， 將混合物冷卻至室溫。之後以蒸餾水與EA進行萃取，有機 層以MgS〇4乾燥，並使用旋轉蒸發器移除溶劑。經管柱層 析法’使用己烷與EA作為沖提液，分離出純化合物B(23g， 74%)。 化合物C之製備 將化合物B(2g，0. 074mol)加至單頸燒瓶中，建立氮 氣環境。加入THF後’混合物於-78°C攪拌10分鐘。滴加 入正-丁基鋰（2· 5M於己烷中）（44. 6ml, 0. llmol)，混合物 於-78°C 攪拌 1 小時。之後’加入 DMF(8. lml，〇. llmmol)， 攪拌10分鐘，混合物於室溫下攪拌4小時。待反應完成後， 加入HC1(2· 5ml)，於室溫下使用蒸餾水與EA進行萃取。 有機層以MgS〇4乾燥，並使用旋轉蒸發器移除溶劑。經管 柱層析法，使用己烷與EA作為沖提液，分離出純化合物 C(19g, 89%)。 化合物D之製備 將9H-苐（60g, 0. 36mol)加至單頸燒瓶中，並於真空 下建立氬氣環境。加入碳酸丙婦酯（5〇〇ml)後，於60°C攪 拌至9H-苐溶解。加入NBS(64g，〇. 36mol)，混合物於6〇°C 授拌1小時。待反應完成後，經蒸顧水過濾所得之固體， 溶於EA中，混合物經蒸顧水萃取。有機層以MgS〇4乾燥， 30 95143 201204807 並使用旋轉蒸發器移除溶劑。使用乙醇進行再結晶，得純 化合物 D(64g，73%)。 化合物E之製備 將化合物 D(40g，〇.16mol)、破（16.9g, 0.066mol)、 碘酸（6. 89g, 0. 039mol) ’加至二頸燒瓶中。加入蒸餾水（30 ml)、醋酸（600ml)與硫酸（14. 4ml)後，混合物於85°C攪拌 4小時。反應完成後，混合物完全冷卻至室溫，並以醋酸 與蒸餾水清洗。經過濾得純化合物E(49g，82%)。 化合物F之製備 將化合物 E(49g，0.13mol)、K0H(33g，0.60mol)與 KI(2.2g, 0.013mol)加至單頸燒瓶中，並於真空下建立氬 氣環境。加入DMSO(無水）（500ml)後，混合物於0°C攪拌 10分鐘。滴加入漠化乙烧（23ml，0. 30mol)，混合物於_1 〇 C 攪拌30分鐘，之後於室溫下攪拌9小時。待反應完成後’ 加入過量蒸餾水產生固體，將固體過濾出，所得固體經二 氯甲烷（MC)萃取。有機層以MgS〇4乾燥，並使用旋轉蒸發 器移除溶劑。經管柱層析法，使用己烷作為沖提液，分離 出純化合物F(37g, 66%)。 化合物G之製備 將化合物 F(30g, 0. 07mol)、°卡°坐（15. 2g, 0. 09mol)、 鋼（2. 5g, 0_ 03mol)、18-冠醚-6(1.4g，0· 005mol)，與 K2C〇3(38.8g，0.28mol)加至二頸燒瓶中，於真空下建立氬 氣環境。加入1，2-二氣苯（250ml)’混合物於180°C回流擾 拌6小時。待反應完成後，使用矽藻土過濾器移除銅，反 31 95143 201204807 應混合物溶於MC中。移除溶劑後，經管柱層析法，使用二 氣甲烷與己烷作為沖提液，分離出純化合物G(23g, 76%)。 化合物Η之製備 將化合物G(20g, 0· 042mol)加至單頸燒瓶中，建立氮 氣環境。加入THF後，混合物於~78。(：攪拌10分鐘。滴加 入正-丁基鋰（2. 5M於己烷中）（40ml, 〇. 〇63mol)，混合物 於-78°C 攪拌 1 小時。之後’加入 DMF(4. 8ml, 0. 063mmol)， 混合物攪拌10分鐘，之後於室溫下攪拌4小時。待反應完 成後’加入HC1(2. 5ml)，冷卻至室溫。使用蒸餾水與ea 萃取。有機層以MgS〇4乾燥，並使用旋轉蒸發器移除溶劑。 經管柱層析法’使用己烷與EA作為沖提液，分離出純化合 物 H(13g，72%)。 化合物I之製備 將化合物H(13g，0. 031mol)與三乙基亞膦酸酯（1〇ml， 0· 062mol)加至單頸燒瓶中。於〇°c加入碘（7. 9g，〇. 〇31 mol)後，混合物攪拌30分鐘，之後於室溫攪拌12小時。 待反應完成後’使用真空昇華器移除亞膦酸酯，並使用蒸 餾水與EA進行萃取。有機層以MgS〇4乾燥，並使用旋轉蒸 發器移除溶劑。經管柱層析法，使用己烷與EA作為沖提 液，分離出純化合物I(16g, 87%)。 化合物91之製備 將化合物 I(16g, 0.029mol)與化合物 C(7.6g, Q.029 mol)加至單頸燒瓶中，於真空下建立氬氣環境。加入thf (600ml)後’混合物於0°C攪拌10分鐘，緩慢加入第三丁 95143 32 201204807 醇鉀（35.7!111’0.035 111〇1)。混合物於〇它攪拌1〇分鐘後， 混合物繼續於室溫攪拌3小時，並以蒸餾水與ea萃取。有 機層以MgS〇4乾燥，並使用旋轉蒸發器移除溶劑。經管柱 層析法，使用己烷與EA作為沖提液，分離出純化合物 91(17g， 89%) 。 σ *HNMR(CDCl3, 200 MHz)： (5=0. 9(6H,m), 1.91(4H,m), 6.95 (2H，m), 7.17(lH，m)，7.25〜7.34(9H，m), 7.41(1Hm) 7. 5〜7. 56(8H, m)，7. 63〜7. 64(3H，m)，7. 87(2H, m) 7 94 (lH，m), 8. 12(lH，m), 8. 55(lH，m)。 MS/FAB : 641. 84(實測值），641. 34(計算值） [製備例2]化合物92之製備Preparation of Compound A 4-, odorous biphenyl (30 g, 0.12 mol) was placed in a one-necked flask to establish an argon atmosphere under vacuum. Tetrahydrofuran (THF) (500 ml) was added, and the mixture was stirred at -78 ° C for 1 hr. n-BuLi (2.5 M in hexane) (77 ml, 0.19 mol) was added, and the mixture was stirred at -78 ° C for 1 hour and 30 minutes. Thereafter, tridecyl borate (21. 9 ml, 0.19 mol) was added at -78 °C. The mixture was stirred at -78 ° C for 30 minutes and then stirred at room temperature for 4 hours. After the reaction was completed, extraction was carried out using distilled water and ethyl acetate (EA). The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. By column chromatography, pure compound A (21 g, 84%) was isolated using hexane and EA as a solvent. Preparation of Compound B bromo-4-iodobenzene (29 g, 〇.l〇m〇l), Compound A (21 g, 0. 10 29 95143 201204807 mol) and tetrakis (diphenylphosphine) (tetrakis ( Triphenylphosphine) Palladium) (5·9 g, 5. lmmol) was added to a two neck (two neck) flask. After the mixture was stirred while adding toluene, 2M K2C 3 (265 ml, 0.5 mol) and ethanol (265 ml) were added. After 10 hours of Tc reflux, when the reaction was completed, the mixture was cooled to room temperature. After that, extraction was carried out with distilled water and EA, the organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. Analytical procedure using pure hexanes and EA as the extract, pure compound B (23 g, 74%) was isolated. Preparation of Compound C Compound B (2 g, 0.074 mol) was added to a one-neck flask to establish a nitrogen atmosphere. After the addition of THF, the mixture was stirred at -78 ° C for 10 minutes. n-butyllithium (2.5 M in hexanes) (44.6 ml, 0.11 mol) was added dropwise, and the mixture was stirred at -78 ° C for 1 hour. Then, 'DMF (8. lml, 〇. llmmol) was added, stirred for 10 minutes, and the mixture was stirred at room temperature for 4 hours. After the reaction was completed, HC1 (2.5 ml) was added, and extraction with EA was carried out at room temperature using distilled water. The organic layer was dried over MgS 4 and the solvent was removed using a rotary evaporator. Purified by column chromatography using hexanes and EA as a solvent to afford pure compound C (19 g, 89%). 9H-indole (60 g, 0.36 mol) was added to a one-necked flask and an argon atmosphere was established under vacuum. After propylene carbonate (5 〇〇ml), it was stirred at 90 ° C until 9H-苐 dissolved. NBS (64 g, 〇. 36 mol) was added, and the mixture was stirred at 6 ° C for 1 hour. The solid obtained by filtration of water was filtered, dissolved in EA, and the mixture was extracted with water. The organic layer was dried over MgS 〇 4, 30 95 143 201204807 and the solvent was removed using a rotary evaporator. Recrystallization was carried out using ethanol to obtain pure compound D. (64 g, 73%) Preparation of Compound E Compound D (40 g, 〇. 16 mol), broken (16.9 g, 0.066 mol), iodic acid (6.99 g, 039 mol) was added to a two-necked flask. After adding distilled water (30 ml), acetic acid (600 ml) and sulfuric acid (14.4 ml), the mixture was stirred at 85 ° C for 4 hours. After the reaction was completed, the mixture was completely cooled to room temperature and washed with acetic acid and distilled water. Pure Compound E (49 g, 82%). Preparation of Compound F Compound E (49 g, 0.13 mol), K0H (33 g, 0.60 mol) and KI (2.2 g, 0.013 mol) were added to a one-neck flask and vacuum An argon atmosphere was set up. After adding DMSO (anhydrous) (500 ml), the mixture was stirred at 0 ° C for 10 minutes. 0. 30mol), the mixture was stirred at _1 〇C for 30 minutes, then stirred at room temperature for 9 hours. After the reaction was completed, 'excess distilled water was added to give a solid, and the solid was filtered, and the obtained solid was extracted with dichloromethane (MC). . The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. Pure compound F (37 g, 66%) was isolated by column chromatography using hexane as a solvent. Preparation of Compound G, Compound F (30 g, 0.07 mol), ° ° ° (15. 2g, 0.09 mol), steel (2.5 g, 0_03 mol), 18-crown-6 (1.4 g, 0) · 005 mol), and K2C〇3 (38.8 g, 0.28 mol) was added to a two-necked flask to establish an argon atmosphere under vacuum. A mixture of 1,2-di-benzene (250 ml) was added and refluxed at 180 ° C for 6 hours. After the reaction is completed, the copper is removed using a diatomaceous earth filter, and the mixture is dissolved in the MC. After removing the solvent, pure compound G (23 g, 76%) was isolated by column chromatography using di-methane and hexanes as a solvent. Preparation of the compound hydrazine Compound G (20 g, 0·042 mol) was added to a one-necked flask to establish a nitrogen atmosphere. After the addition of THF, the mixture was at ~78. (: stirring for 10 minutes. Add n-butyllithium (2.5 M in hexane) (40 ml, 〇. 〇 63 mol), and the mixture was stirred at -78 ° C for 1 hour, then added 'DMF (4.8 ml, 0. 063 mmol), the mixture was stirred for 10 minutes, then stirred at room temperature for 4 hours. After the reaction was completed, 'HC1 (2.5 ml) was added, and cooled to room temperature. Extracted with distilled water and ea. The organic layer was dried with MgS? And use a rotary evaporator to remove the solvent. By column chromatography 'using hexane and EA as the extract, the pure compound H (13 g, 72%) was isolated. Compound I was prepared as compound H (13 g, 0. 031 mol) and triethylphosphonite (1 〇ml, 0·062 mol) were added to a one-necked flask. After adding iodine (7.9 g, 〇. 31 mol) at 〇 °c, the mixture was stirred for 30 minutes. After stirring for 12 hours at room temperature. After the reaction was completed, the phosphinate was removed using a vacuum sublimator and extracted with EA using distilled water. The organic layer was dried over MgS 4 and the solvent was removed using a rotary evaporator. Column chromatography, using hexane and EA as the extract, separated the pure compound I (16 g, 87%). Compound I (16 g, 0.029 mol) and compound C (7.6 g, Q.029 mol) were added to a one-necked flask, and an argon atmosphere was established under vacuum. After adding thf (600 ml), the mixture was stirred at 0 ° C. Minutes, slowly add the third butyl 95143 32 201204807 potassium alkoxide (35.7! 111'0.035 111 〇 1). After stirring the mixture for 1 〇, the mixture was stirred at room temperature for 3 hours and extracted with distilled water and ea. The layer was dried over MgS(R) 4 and solvent was removed using a rotary evaporator. hexanes and EA were used as a solvent, and pure compound 91 (17 g, 89%) was isolated. σ *HNMR (CDCl3, 200 MHz): (5=0. 9(6H,m), 1.91(4H,m), 6.95 (2H,m), 7.17(lH,m), 7.25~7.34(9H,m), 7.41(1Hm) 7. 5~7. 56(8H, m), 7. 63~7. 64(3H,m), 7. 87(2H, m) 7 94 (lH,m), 8. 12(lH,m) , 8. 55 (lH, m) MS/FAB: 641. 84 (found), 641. 34 (calc.) [Preparation 2] Preparation of Compound 92

化合物A之製備 將4-演代聯苯（3〇g，〇12m〇1)加入單頸錐形瓶中於 真空下建立氩氣環境。加入THF(500ml)後，於-78t：授拌 10分鐘。滴加入n-BuLi(2. 5M溶於己烷中）（77ml，〇. 19 mo1)。混合物於-78t：攪拌1小時30分鐘’並於-78ΐ加入 33 95143 201204807 三曱基刪酸醋（21.91111，〇.19111〇1)。混合物於_78°〇授摔30 分鐘後’於室溫下攪拌4小時。待反應完成後，混合物使 用蒸餾水與EA進行萃取。有機層係以MgS〇4乾燥，並使用 旋轉蒸發器移除溶劑。經管柱層析法，使用己烷與EA作為 沖提液，分離出純化合物A(21g，84%)。 化合物B之製備 將 1-溴-4-碘化苯（29g，0. lOmol)、化合物 A(21g， 0. lOmol)與四（三苯基膦）鈀（5· 9g，5· lmmol)加至二頸燒 瓶中。於加入曱苯同時攪拌混合物。加入2MK2C03(265ml， 0. 5mol)與乙醇（265ml)後，混合物於l〇〇°c回流授拌5小 時後，反應完成時，混合物冷卻至室溫，並以蒸餘水與EA 進行萃取，有機層以MgSCh乾燥，並使用旋轉蒸發器移除 溶劑。經管柱層析法，使用己烧與EA作為沖提液，分離出 純化合物B(23g，74%)。 化合物C之製備 將化合物B(2g, 0. 074mol)加至單頸燒瓶中，建立氮 氣環境。加入THF後，混合物於-78°C，!互溫下擾拌1〇分鐘。 滴加入正-丁基裡（2· 5M於己院中）（44. 6ml，〇. Hm〇i)，混 合物於-78°C攪拌1小時。加入DMF(8. lml，〇. iimm〇i)後， 混合物攪拌10分鐘，之後於室溫下攪拌4小時。待反應完 成後，加入HC1 (2. 5ml)。混合物冷卻至室溫，使用蒸顧水 與EA進行萃取。有機層以MgS〇4乾燥’並使用旋轉蒸發器 移除溶劑。經管柱層析法’使用己烷與EA作為沖提液，分 離出純化合物C(19g, 89%)。 95143 34 201204807 化合物J之製備 將化合物C(20g，0.077mol)加至單頸燒瓶中，建立氮 氣環境。加入乙醇（300ml)後，混合物於0°C之恆溫下攪拌 10分鐘。加入硼氫化鈉（3. 2g, 0· 085mol)後，混合物於室 溫下攪拌6小時。待反應完成後，加入HC1 (5ml)，混合物 以蒸餾水與EA萃取。有機層以MgSCh乾燥，並使用旋轉蒸 發器移除溶劑。經管柱層析法，使用己烷與EA作為沖提 液，分離出純化合物J(17. 4g，86%)。 化合物K之製備 將化合物1(158，0.057111〇1)與三乙基亞膦酸酯（19.4 ml, 0. 12mol)加至單頸燒瓶中。於〇°C加入碘（14. 5g， 〇· 〇57m〇l)後，混合物攪拌30分鐘，之後於室溫攪拌12 小時。待反應完成後，使用真空昇華器移除亞膦酸酯，並 使用蒸餾水與EA進行萃取。有機層以MgS〇4乾燥，並使用 旋轉蒸發器移除溶劑。經管柱層析法，使用己烷與EA作為 沖提液，分離出純化合物K(16g, 72%)。 化合物L之製備 將1-胺基-4-溴化萘（60g, 0.27mol)加至單頸燒瓶中， 於真空下建立氬氣環境。加入乙腈（500ml)後，混合物於 授拌至ι_胺基-4-漠化萘溶解。亞硝酸第三丁酯（|2g， 48ml，〇.4im〇i)與溴化銅（73g，〇.32mol)於室溫下授拌3 小時。待反應完成後，加入IN HC1水溶液（600ml)並授掉。 待所知固體過遽出後’該固體以蒸镏水與醚類清洗。經管 化得純化合物L(76g，85%)。 35 95143 201204807 化合物Μ之製備 將化合物 L(40g，0.12mol)、咔唑（24. lg, 〇. i4m〇l)、 銅（3· 3g，〇· 05mol)、18-冠醚-6(2. 3g, 0. 009mol)，與 K2CO3 (66.3g，〇.48mol)加至二頸燒瓶中，於真空下建立氬氣環 境。加入1，2-二氯苯（250ml)，混合物於180°C回流6小時。 待反應完成後’使用梦藤土過濾、器移除銅，反應滿合 物溶於MC中。移除溶劑後，經管柱層析法，使用二氯甲烷 與己烷作為沖提液，分離出純化合物M(36g，81%)。 化合物N之製備 將化合物M(20g，〇· 〇54mol)加至單頸燒瓶中，建立氮 氣環境。加入THF後，混合物於-78°C攪拌10分鐘。滴加 入正-丁基鋰（2. 5M於己烷中）（32ml，〇. 〇81mol)，混合物 於-78°C攪拌1小時。加入DMF(6.3ml，0.081mol)後，混 合物攪拌10分鐘，之後於室溫下攪拌4小時。待反應完成 後’加入HC1 (3ml)。混合物冷卻至室溫，並以蒸餾水與EA 清洗。有機層以MgS〇4乾燥，並使用旋轉蒸發器移除溶劑。 經管柱層析法，使用己烷與E A作為沖提液，分離出純化合 物 N(12.4g， 71%)。 化合物92之製備Preparation of Compound A 4-Derivative biphenyl (3 〇g, 〇12m〇1) was placed in a single-necked Erlenmeyer flask to establish an argon atmosphere under vacuum. After adding THF (500 ml), it was mixed at -78 t: for 10 minutes. n-BuLi (2.5 M dissolved in hexane) (77 ml, 〇. 19 mo1) was added dropwise. The mixture was stirred at -78 t for 1 hour and 30 minutes' and added at -78 Torr to 33 95143 201204807 tridecyl vinegar (21.91111, 〇.19111〇1). The mixture was stirred at _78 ° for 30 minutes and then stirred at room temperature for 4 hours. After the reaction was completed, the mixture was extracted with distilled water using EA. The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. By column chromatography, pure compound A (21 g, 84%) was isolated using hexane and EA as a solvent. Preparation of Compound B 1-Bromo-4-iodobenzene (29 g, 0.1 mol), Compound A (21 g, 0.1 mol) and tetrakis(triphenylphosphine)palladium (5·9 g, 5·lmmol) In a two-necked flask. The mixture was stirred while adding toluene. After adding 2MK2C03 (265 ml, 0.5 mol) and ethanol (265 ml), the mixture was refluxed for 5 hours at 10 ° C. After the reaction was completed, the mixture was cooled to room temperature, and extracted with distilled water and EA. The organic layer was dried with MgSCh and the solvent was removed using a rotary evaporator. By column chromatography, pure compound B (23 g, 74%) was isolated using hexane and EA as a solvent. Preparation of Compound C Compound B (2 g, 0. 074 mol) was added to a one-necked flask to establish a nitrogen atmosphere. After the addition of THF, the mixture was stirred at -78 ° C for 1 Torr at room temperature. Add n-butyl hexane (2.5 M in a hospital) (44.6 ml, 〇. Hm〇i), and the mixture was stirred at -78 ° C for 1 hour. After adding DMF (8.1 ml, 〇. iimm〇i), the mixture was stirred for 10 minutes and then stirred at room temperature for 4 hours. After the reaction was completed, HC1 (2.5 ml) was added. The mixture was cooled to room temperature and extracted with EA using steam. The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. Pure compound C (19 g, 89%) was isolated by column chromatography eluting with hexane and EA. 95143 34 201204807 Preparation of Compound J Compound C (20 g, 0.077 mol) was added to a one-necked flask to establish a nitrogen atmosphere. After adding ethanol (300 ml), the mixture was stirred at a constant temperature of 0 ° C for 10 minutes. After sodium borohydride (3.2 g, 0·085 mol) was added, the mixture was stirred at room temperature for 6 hours. After the reaction was completed, HCl (5 ml) was added, and the mixture was extracted with distilled water and EA. The organic layer was dried with MgSCh and the solvent was removed using a rotary evaporator. Pure compound J (17.4 g, 86%) was isolated by column chromatography using hexanes and EA. Preparation of Compound K Compound 1 (158, 0.057111〇1) and triethylphosphonite (19.4 ml, 0.12 mol) were added to a one-necked flask. After adding iodine (14.5 g, 〇·〇 57m〇l) at 〇 ° C, the mixture was stirred for 30 minutes and then stirred at room temperature for 12 hours. After the reaction was completed, the phosphinate was removed using a vacuum sublimator and extracted with distilled water using EA. The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. By column chromatography, pure compound K (16 g, 72%) was isolated using hexane and EA as a solvent. Preparation of Compound L 1-Amino-4-brominated naphthalene (60 g, 0.27 mol) was added to a one-necked flask to establish an argon atmosphere under vacuum. After the addition of acetonitrile (500 ml), the mixture was stirred and dissolved in m-amino-4-ylidene naphthalene. Tert-butyl nitrite (|2g, 48ml, 〇.4im〇i) and copper bromide (73g, 〇.32mol) were mixed for 3 hours at room temperature. After the reaction was completed, an aqueous solution of IN HCl (600 ml) was added and then transferred. After the solid is overdrawn, the solid is washed with distilled water and ether. Pure compound L (76 g, 85%) was obtained by chromatography. 35 95143 201204807 Preparation of compound hydrazine Compound L (40 g, 0.12 mol), carbazole (24. lg, 〇. i4m〇l), copper (3.3 g, 〇· 05 mol), 18-crown-6 3g, 0. 009mol), and K2CO3 (66.3 g, 〇.48 mol) were added to a two-necked flask to establish an argon atmosphere under vacuum. 1,2-Dichlorobenzene (250 ml) was added, and the mixture was refluxed at 180 ° C for 6 hours. After the reaction is completed, the copper is removed using a Mengteng filter, and the reaction mixture is dissolved in the MC. After removing the solvent, pure compound M (36 g, 81%) was isolated by column chromatography using dichloromethane and hexane as solvent. Preparation of Compound N Compound M (20 g, 〇·〇 54 mol) was added to a one-necked flask to establish a nitrogen atmosphere. After the addition of THF, the mixture was stirred at -78 ° C for 10 min. n-Butyllithium (2.5 M in hexane) (32 ml, 〇. mol 81 mol) was added dropwise, and the mixture was stirred at -78 ° C for 1 hour. After adding DMF (6.3 ml, 0.081 mol), the mixture was stirred for 10 minutes and then stirred at room temperature for 4 hours. After the reaction was completed, HCl (3 ml) was added. The mixture was cooled to room temperature and washed with distilled water and EA. The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. Purified compound N (12.4 g, 71%) was isolated by column chromatography using hexanes and EtOAc. Preparation of Compound 92

將化合物 K(10g，〇.〇26mol)與化合物 N(8 4g，0.026 mol)加至單頸燒瓶中，於真空下建立氬氣環境。加入THF (600ml)後，於〇t攪拌10分鐘，緩慢加入第三丁醇_(1.〇M 於THF中）（31ml，〇· 〇31mol)。混合物於攪拌1〇分鐘， 之後繼續於室溫下攪拌混合物3小時，並以蒸餾水與£八 36 95143 201204807 萃取。有機層以MgS〇4乾燥，並使用旋轉蒸發器移除溶劑。 經管柱層析法，使用己院與EA作為沖提液，分離出純化合 物 92(12g， 84%)。 泔丽吖00(：13，200 ^!1^):(5=6.95(211，111)，7.25〜7.33 (7H,m), 7.41(lH,m), 7. 5~7. 55(13H, m), 7. 9~7. 94(3H, m), 8. 08〜8. 12(2H，m)，8. 55(lH，m)。 MS/FAB : 547. 69(實測值），547. 23(計算值）。 化合物1至90係依據製備例1與2之流程製備。如 此製備之有機電場發光化合物之1H NMR與MS/FAB數據列Compound K (10 g, 〇. 〇 26 mol) and compound N (8 4 g, 0.026 mol) were added to a one-necked flask to establish an argon atmosphere under vacuum. After adding THF (600 ml), it was stirred for 10 minutes at 〇t, and the third butanol _ (1. 〇M in THF) (31 ml, 〇·〇 31 mol) was slowly added. The mixture was stirred for 1 minute, then the mixture was further stirred at room temperature for 3 hours and extracted with distilled water and £8,966,0,0,0,0,0,028 The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. The purified compound 92 (12 g, 84%) was isolated by column chromatography using hexanes and EA as a solvent.泔丽吖00(:13,200 ^!1^):(5=6.95(211,111), 7.25~7.33 (7H,m), 7.41(lH,m), 7. 5~7. 55(13H , m), 7. 9~7. 94(3H, m), 8. 08~8. 12(2H,m), 8. 55(lH,m) MS/FAB : 547. 69 (measured value) 547. 23 (calculated value) Compounds 1 to 90 were prepared according to the procedures of Preparation Examples 1 and 2. 1H NMR and MS/FAB data columns of the thus prepared organic electroluminescent compound

於表卜在下表1中，，'L"表示《Rz)tIn Table 1 below, 'L" means "Rz)t

37 95143 201204807 表1 化合物 L Y Ή NMR(CDCb, 200 MHz) MS/FAB 實測值 計算值 1 TL1 TAR1 δ « 6.95(2Ht m), 7.25-7.33(7Ht m), 7.41 (1H, m)( 7·5-7·5β(9Η, m), 7.62~7·64(5Η· m), 7.94(1 H, m), 8.12(1H( m)t 8.55(1H, m) 497.6 497.2 2 TL1 TAR6 δ = 6.95(2H, m), 7.25-7.33(7H, m), 7.41 (1H, m), 7.5-7.56(9H, m), 7.63-7.68(7H, m), 7.79(2H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m) 5737 573.2 3 TL1 TAR11 δ = 6.95(2H, m), 7.25-7.41 (12H, m), 7.5~7.56(11H. m), 7.63~7.66(4H, m), 7.91-7.96(9H, m), 8.08-8.12(2H. m). 8.55(3H, m) 850.1 849.3 4 TL1 TAR16 δ = 6.95(2Ht m), 7.25-7.41 (13H, m), 7.5~7.56(8H, m), 7.63~7.64(3H, m), 7·^>7.94{5Η· m). 8.12(1H, m), 8.55(1 H. m) 671.8 671.3 5 TL1 TAR20 δ = 6.95(2H, m), 7.25-7.33(7H. m), 7.41(1H, m), 7.5-7.56(7Hf m), 7.63~7.64(3H, m), 7.7-7J1(4H, m), 7.8(1H, m)f 7.9-8(3H, m>, 8.1-8.12(2Hf m), 8.55(1H, m) 621.8 621.2 6 TL1 THAI δ = 6.95(2H, m), 7.25-7.33(7H, m). 7.41-7.52(8H, m), 7.59-7.63(3H, m), 7.77(1 H, m), 7.9-7.94(2H, m), 8.12(1H, m), 8.36(1 H, m), 8.55(1 H, m) 498.6 498.2 7 TL1 THA10 δ = 6.95-€.99(2H, m), 7.25-7.35(9H, m), 7.41~7.52(8H, m), 7.59-7.63(3H, m), 7.94(1 H, m), 8.12(1H,m), 8.55(1H, m) 503,7 503.2 8 TL1 THA7 δ = 6.95(2H. m), 7.25-7.33(8H, m). 7.41 (1H. m). 7.5~7.56(7H. m), 7.63-7.64(3H, m), 7.83(1 H, m). 7.94(1 H, m), 8.12(1 H, m), 8.55(1 H. m), 8.7(2H, m) 549.7 549.2 9 TL1 TY2 δ = 6.95(2H, m), 7.25~7.33(7rt, m), 7.41 (1H, m), 7.5~7.5β(9Η, m), 7.63-7.79(11H. m), 7.94(1H, m), 8.12(1H,m), 855{1H,m) 655.8 655.2 10 TL1 THA26 δ = 6.54(1 H. m), 6.82(1 H, m), 6.95~B.99(2H, m), 7.07(4H, m), 7.25-7.33(7H, m), 7.41~7.52(8H, m), 7.59-7.63(3H, m), 7.94(1 H, m), 8.12(1 H, m), 6197 619.2 38 95143 201204807 8.55(1 H, m) 11 TL1 TY7 δ = 6.95(2Ht m), 7.25(7H( s), 7.25-7.33(2H, m), 7.41(1H, m), 7·5-7.56<9Η, m), 7,63~7.68(5H，m)， 7·79(4Η· m), 7_94(1H, 8.12(1H, m>· 8_55(1H. m) 711.9 711.2 12 TL1 THA21 δ = 6.95-6.99(2H, m), 7^5(5H, m), 7.26{2H, s), 7.29~7.33(2H, m), 7.41~7.52(8H, m), 7.59-7.63(3H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m) 579.6 579.2 13 TL1 TF5 δ « 1.48(6H, m), 2.02(4Ht m). 6.95(2H, m), 7.17(1H, m), 7.25-7.34(9H, m). 7.41(1H, m), 7.5-7.56(8H, m), 7.63-7.64(3H, m), 7.87(2H, m), 7.94(1Ht m). 8.12(1H, m), 8.55(1^ m) 653.9 653.3 14 TL1 TF17 δ = 2.26(6H, s), 5{1H, s), 6.95(2H, m), 7.17(1 H, m), 7.25-7.34(9H, m), 7.41(1 H, m), 7.5~7.56(8H, m), 7.63-7.64(3H, m), 7.87(2H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H,m) 628.8 628.3 15 TL1 7F10 δ = 3.2(3H, s), 3.81(2H, s), 6.41(1H, m), 6.49(1 H, m), 6.56(1 H, m)； 6.95-7.03(5H, m), 7.25-7.33{7H, m), 7.41(1 H, m), 7.5-7.56(7H, m). 7.63-7·64(3Η. m), 7.94(1 H, m), 8.12(1 H. m), 8.55(1 H, m) 614.8 614.3 16 TL1 TF15 δ = 3.2(3H, s), 6.61 (1H, m), 6.86(1 H. m), 6.94~6.99(4H, m), 7.25-7.34(13H, m), 7.41 (1H, m), 7.5~7.52(5H, m). 7.63(^, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m) 600.7 600.3 17 TL2 TAR4 δ = 3.81(2H, s), 6.51(2H, m), 6.69(2H, m), 6.9&-7.01(6H, m). 7.25(4H, m), 7.38-7.41 (5H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.88-7.9(4H, m) 611.8 611.3 18 TL2 TAR9 δ = 3.81 (2H, s), 6.51 (2H, m), 6.69(2H, m), 6.95~7.01(6H, m). 7.25(4H, m), 7.38-7.41 (9H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.88-7.91 (8H, m) 788.0 787.3 19 TL4 TAR14 δ = 6.59(2H, m), 6.77(2H, m), 6.89(2H, m), 6.91 (1H, s), 6.92-6.95(^, m), 7.25(4H, m), 7.41 (1H. m), 7.51-7.56(6H. m), 7.64(2H, m), 7.82-7.88(4H. m), 8.12(2H, m), 8.93(2H, m), 9.09(1H, s) 663.8 663.3 39 95143 201204807 20 TL4 TAR18 δ = 6.59(2Η, m), 6.77(2Η, m), β.89-6.95(7Η, m), 7·25(4Η, m), 7.41(1Η, m), 7.51-7.56(6Η, m). 7.64(2Η, m), 7.82-7.88(2Η, m), 7.98(1 Η, m), 8.12(2Η, m). 8·93(1Η, m), 9.09(1Η, m) 613.7 613.2 21 TL5 THA29 δ = 6；95~6.97(4Η, m), 7.12-7.25(11 Η. m). 7.4W.44(3H, m). 7.51 ~7.52(4Η. m), 7.59(2Η, m), 7.72(1 Η, m), 7.83(1 Η, m), 8.25(1 Η, m), 8.5(1 Η, m), 8.97(1Η, m) 631.8 631.2 22 TL5 THM δ 甲 6.95~6.99(4Η, m), 7.16-7.25(10Η. m), 7.41~7.44(3Η, m), 7.51-7.52(4Η, m), 7.59(2Η, m), 8.25(1 Η, s) 532.7 532.2 23 TL6 THA13 δ = 2.88(4Ht m)f 6.58(2Ht m), 6.76(2H( m), 6.95-7.04(6Ht m), 7.25{4H, m). 7.41-7.44(3H, m). 7.51-7.52(4H( m), 7.59(2H, m) 533.7 533.2 24 TL6 THA18 δ 〇 2.88(4H, m). 6.58(2H, m), 6.73-6.76(3Ht m), 6.95(2H, m), 7.02-7.04(4H, m), 7.11(1H, m), 7·25(4Η, m), 7.41(1H, m}. 7.51-7.56(6H, m), 7.64(2H, m), 9.23(1 H, S) Λ 582.8 582.2 25 TL6 THA25 δ = 2.88(4H, m), 6.3(1 H, m), 6.58(2H, m), 6.76(2H, m). 6.95-7.04(6H, m), 7.25-7.28(5H, m), 7.35(1 H, m), 7.41-7.44(3H, m), 7.51-7.52(4H, m), 7.59(2H, m), 7.73(3H, m) 696.0 695.2 26 TL7 TY4 δ * 6.63(2H, m), 6.69(2H, m), 6.81 (2H, m), 6.95-7!〇5(6H, m). 7.25(6H. m), 7.41(1 H. m), 7.51~7.56(10H, m), 7.64(2H, m), 7.79(2H, m) 667.8 667.3 27 TL7 TF1 δ = 6.58-6.63(3H, m), β.75-6.81(3Η, m), 6.95-7.05(6H. m), 7.11(4H, m), 7.25~7.26(8H, m), 7.33(4H, m), 7.41(1 H, m), 7.51-7.56(7H, m), 7.62-7.64(3H, m), 7.71 (1H, m), 7.87(1 H, m) 764.0 1 763.3 28 TL7 TF6 δ * 1.51(4H, m), 2.09(4H, m),-6.58-6.63(3H, m), 6.75-6.81 (3H, m), 6.95-7.05(6H. m), 7.25(6H, m). 7.41(1H, m), 7.51-7.56(7H, m). 7.62-7.64(3H, m), 7.71(1H,m), 7.87(1H, m) 665.9 665.3 29 TL7 TF18 δ = 5(1 H, s), 6.58~6.63(3H, m), 6.75-6.81 (5H, m), 6.95-7.05(6H, m), 7.23-7.25(1 OH, m). 7.33{4H, m), 779.0 778.3 40 95143 201204807 7.41(1Η· m)· 7·51-7·56(7Η, m), 7·62-7.64(3Η· m), 7.71(1Η, m),7.87(1Hlm) 30 TL7 TF11 δ = 3.2(3Η, s), 5.7(1 Η, m), 5.91(1 Η, m), 6.49(1 Η. m), 6.63-6.67(3Η, m), 6.81(2Η, m), 6.92~7.05(7Η, m), 7.13(1 Η, m), 7.25(6Η, m), 7.41(1 Η, m), 7.51-7.56(6^ m), 7.64(2Η, m) 642·β 642.3 31 TL8 THA27 δ = 6·59(1Η· s), 6·69(2Η· m)· 6·81-6.87(4Η· m). 7.1^, s)t 7.16(2Η· m), 7·25(4Η, m), 7.41-7.59(13Η, m), 7.85(2Η, m) 884.7 887.0 32 TL8 TY5 δ = 6.69(4Η, m), 6.87(2Η, m), 6.95(2Η, m), 7.16(2Η, m), 7.25(4Η, m), 7.41-7.56(13Η, m), 7.64(2Η, m), 7.76~7.85(6Η. m) 733-9 733.3 33 TL8 TF2 δ = 6.58(1Η, m), 6.69~6.75(3H, m). 6.87(2Η, m), 6.95(2Ηι m), 7.16-7.25(10Η_ m), 7.35(2Η, m), 7.41-7.56(12Η, m), 7.62~7.64(3Η, m), 7.71-7J5(3H, m), 7.85-7.87(3Η, m) 812.0 811.3 34 TL8 TF7 δ = 3.49(4Η, s), 6.58(1Η, m), 6·69~6.75(3Η, m>, 6.87(2Η, m), 6.95(2Η, m), 7.16-7.25(10Η, m), 7.41~7.56(12Η, m), 7.62-7.64(3Η, m), 7.71(1Η, m). 7.85-7.87(3Ht m) 764.0 763.3 35 TL8 TF13 δ = 3.2(3Η, m), 5.88(1 Η, m), 6.47(1 Η, m), 6.69(2Η, m), 6.87-6.97(5Η, m), 7.16-7.25(11 Η, m), 7.41~7.54{9Η, m), 7.85(2Η, m) 682.9 682.2 36 TL8 TF16 δ = 3.2(3Η, m), 5.8(1Η, m), 6.01(1Η, m), 6.57(1Η, m), 6.69(2Η, m)t 6.87~β.92(3Η, rr〇, 7·16(2Η, m), 7^5(8Η, m), 7.32(1Η, m), 7.41-7.54(11 Η, m). 7.63(1 Η, m), 7.85(4Η, m) 726.9 726.3 37 TL9 TAR7 δ = 3.82(3Η, s), 6.95(2Η, m), 7.25(12Η, m), 7.41~7.42(3Η. m). 7.51~7.64(14Η, m), 7.79(1Η, m), 8.17-8.18(2Η, m) 663.85 663.29 38 TL9 TAR17 δ = 3.82{3Η, s). 6.95(2Η, m), 7i5(4H, m), 7.41~7.42(3Η, m). 7.51~7.64(10Η, m), 7.71 (2Η, m), 7·79{1Η· m), 7·98-8·04(2Η, m), 8.12-8·18(4Η, m), 9.09(1 Η, m), 9.15(1 Η, m) 611.77 611.26 41 95143 201204807 39 TL9 THA2 δ = 3.82(3Η, s), 7.2~7.25(5Η, m), 7.41(1Η, m). 7.42-7.51 (14Η, m), 7.79-7.83(2Η, m). 8.17-8.18(2Η, m), 8.85(1 Η, m) 512-64 512.23 40 TL9 THA15 δ = 3·82(3Η, s>, 6·95-6·99(2Η· 7·25(4Η, m)· 7.41-7.44(5Η, m). 7.51-7.52(4Η, m), 7.59-7.62(4Η, m), 7.79(1Η, m), 8.17-8.18(2H, m), 8.63(2Η, m) 569.72 569.19 41 TL9 THA25 δ = 3.82(3Η, 6), 6.95~6.99(2Η, m), 7.25{4Η, m), 7.35(1Η, m), 7.41-7.44(5Η, m), 7.51-7.52(4Η, m), 7.59-7.62(4Η, m). 7.73~7.79(6Η, m), 8.17~8.18(2Η, m) 681.93 681.16 42 TL9 TF1 δ =. 3.82(3Η, s), 6.95(2Η, m), 7.11(4Η, m). 7.25~7.26(6Η, m), 7.33(4Η, m), 7.41-7.42(3Η. m), 7.51-7.56(12Η, m), 7.71-7.79(3Η, m). 7.87~7.93(2Η, m), 8.17-8.18(2Η, m) 751.95 751.32 43 TL9 TF1B /，、· δ = 3.82(3Η, 3), 5(1 Η, s)( 6J7(2H, m)( 6.95(2Η, τη), 7.23-7.25(8Η, τη), 7.33(4Η, m), 7.41-7.42(3Η, m), 7.51-7.56(12Η, m), 7·71-7·79(3Η, m), 7.87~7.93(2Ht m)( 8.17-8.18(2Η, m) 766.97 766.33 44 TL9 TF16 δ = 3·2(3Η, s), 3·82(3Η, s). 6,57-6.59(2Η, m〉, 6·88^6·95(4Η, m), 7·25(4Η, m)· 7.41(1 Η· m)· 7.42(2Η, m), 7.47(2Η( m), 7.51-7.57(12Η, m), 7·79-7·85(3Η· m), 8·17-8·18(2Η· m) 690.87 690.30 45 TL10 TAR10 δ = 1.72(6Η, s), 3.2(3Η, s), 6.52(1 Η, m), β.69(2Η, m), 6.78(1Η, m), 6.95(2Η, m), 7.05-7.14{3Η. m), 7.25(8Η, m), 7.39~7.41(5Η, m). 7.51-7.56(8Η, m), 7.64(4Η, m), 7.91 (4Η, m) 806.04 805.37 46 TL10 TAR19 δ = 1.72(6Η, s), 3.2(3Η, s), 6.52(1Η, m), 6.69ί2Η, m), 6.78〇H, m), 6.95{2Η, m), 7.05-7.14(3Η, m), 7.25(4Η, m), 7.41(1Η, m), 7.51-7.56(6Η, m), 7.64(2Η, m), 7.71(2Η, m), 7·β2-7.88(3Η, m), 8.04(1Η, m), 8.12(1Η, m), 8.18(1Η, m) 677.87 677.31 47 TL10 THA9 δ = 1.72(6Η, s), 3.2(3Η, s), 6.52(1 Η, m), 6.69(1 Η, m), 6.78-6.82(2Η, m), 6.95~7.14(7Η, m), 7.25(4Η, m), 7.41~7.44(3Η, m), 7.51-7.52(4Η, m), 7.59(2Η. m) 543.70 543.26 42 95143 201204807 48 TL10 TY1 δ = 1.72(6H, s), 3·2(3Η, s), 6·52《1Η, m), 6·69(2Η, m)f 6.78(1H( m), 6.95{2H, m), 7.05-7.14(5H, m), 7.25(6H, m)· 7.41(1H· m>, 7.5W.56(8H. m), 7·64(2Η· m>, 7·85(2Η，m), 7·95(2Η, m) 695.89 695.32 49 TL10 THA28 δ = 0.14(6H, s), 1.72(6H, s), 3.2(3H, s), 6.52(1 H, m), 6.69(1 H. m), 6.78(1 H, m), 6.95-7.03(3H, m). 7.04(2H, S), 7.05-7.14(4H, m), 7.25(4H, m). 7.35(2H, m), 7.41-7.44(3H, m), 7.51-7.52(4H, m), 7.59(2H,m), 7.89(1 H,m) 750.10 749.26 50 TL10 TF4 δ = 1.72(6Η, s), 32(3H, s)( 6.52(1H# m)( 6.69(2H, m)· 6·78^.81(3Η· m), 6·95(2Η·.πι), 7·05-7·14《3Η· m), 7,25(4H, m). 7·41(1Η, m), 7,48~7·56<9Η, m), 7.63-7.64(3^ m), 7 J1-7.77(2H, m), 7.87-7.93{2H( m), 8·51(2Η. m) 793.99 793,35 51 *；· TL10 TF9 δ = 0.66(6H, s), 1.72(6H, s), 3.2(3H, s), 6.52(1 H, m), 6.69(2H, m), 6.78(1 H, m), 6.95(2H, m), 7.05-7.1^, m), 7.25(4H, m), 7.35(1H, m), 7.41 (1H, m), 7.51-7.56(6H, m), 7.64~7.66{3HP m), 7.76(1 H, m), 7.82(1 H, m), 7.89(1 H, m), 7.95(1 H, m) 685.97 685.32 52 TL12 TAR3 δ = 3.2(3H, s), 6.56(1 H, m), 6.73(1 H, m), 6.82(1 H, m). 6.92-6.98(5H, m), 7.07(1 H, m), 7.25(4H, m). 7.41 (1H, m), 7.51-7.64(10H, m), 7.73(1 H, m), 7.8(1 H, m). 7.92-7.95(2H, m) 577.71 577.24 53 TL12 TAR13 δ = 3.2(3H, s), 6.56(1H, m), 6.73{1H, m). 6.82(1H, m), 6.92-6.98(5H, m), 7.07(1 H. m). 7.25(4H, m), 7.41(1 H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.82-7.88(2H, m), 7.98-8.04(2H, m), 8.12(2H, m), 8.18(1H, m), 8.93(1H, m), 9.09(1H, m), 9.15(1H, m) 677.83 677.27 54 TL12 THA6 δ = 3^(3H, s), 6.56(1 H, m), 6.73(1 H, m), 6.82(1 H, m). 6.92-6.98(5H. m), 7.07(1 H, m), 7.25(4H· m), 7.41-7.44(3H, m), 7.51~7.52(4H, m), 7.59(2H, m), 8.03(1 H, m). 8.12(1 H, m). 8.27(1H, m), 8.5(^, m), 8.97(1 H.m) 578.70 578.24 55 TL12 THA12 δ = 3.2(3H, s), 6.56(1H, m), 6.73(1H. m). 6.82(1H, m). 6.92-6.99(5H, m), 7.25(4H, m), 7.41~7.44(4H, m), 7.51-7.52(4H, m), 7.59(2H, m) 519.59 519.19 43 95143 201204807 56 TL12 ΤΗΑ22 δ = 3.2(3Η, s), 6.56(1 Η, m), 6.73(1 Η, m). 6.82(1 Η, m), 6.92-6.99(5Η, m), 7.07(1 Η, m), 7.25(4Η, m), 7.35(1Η, m). 7.41-7.44(3Η, m), 7.51-7.52(4Η, m), 7.59(2Η, m), 7.73(3Η, m) 615.81 615.17 57 TL12 ΤΥ5 δ = 3.2(3H, s), 6.56(1Η, m), 6·73(1Η, m)· 6.82(1Η, m)( 6.92-6.98(5Η, m), 7.07(1Η, m), 7.25(6Η, m), 7.41(1Η, m)( 7.51-7.56(8Η, m), 7.64(2Η. m), 7.79-7.85(4Η, m) 687.85 687.23 58 TL12 TF7 δ = 3·2(3Η· s), 3.49(4Η· s), 6.56(1Η, m)· 6,73(1Η· m), 6·82<1Η, m). 6·92-β·98(5Η· m>, 7.07《1Η, m>· 7.2-7.25(8Η, m), 7.41(1Η, m), 7.51-7.56(7Η, m), 7.63-7.64(3Η, ητ〇· 7·71-7·77(2Η, m), 7.87-7·93(2Η, m) 717.89 717.30 59 TL12 TF12 δ = 3.2(6Η, s), 6.53-β.5β(2Η, m), 6.73(1 Η, m), 6.82~6.98(8Η, mj, 7.07-7.11(2Η, m), 7.22-7.28(6Η, m), 7.41(1 Η, m), 7.51-7.56(6Η, m), 7.64(2Η, m) 709.73 710.18 60 TL13 TAR6 δ =* 3,2(3Η, 8), 6.9~6.97{5Η, m), 7.1β-7.25(12Η, m), 7.41(1 Η, m), 7.51-7.56(8Η, m), 7.64(4Η, m) 619.82 619.23 61 TL13 TAR16 δ = 3.2(3Η, s), 6.9~6.97(5Η. m), 7.16-7.25(8Η, m), 7.39-7.41 (5Η, m), 7.51-7.64(1 OH, m), 7.91-7.97(4H. m) 717.92 717,25 62 TL13 THAI 6 = 35(3H, s), 6.95-6.97(3H, m). 7.16-7.25(8H, m), 7.41-7.52(1 OH, m), 7.59(2H, m), 7.97(1 H, m), 8.33(1 H, m) 544.71 544.20 63 TL13 ΤΗΑ7 δ = 3.2(3H, s), 6.9-6.97(5H, m), 7.16-7.25(8H, m), 7.41 (1H, m), 7.51~7.56(6H, m), 7.64(2HP m), 7.9(2H, m), 8.74(2H, m) 595.75 595.21 64 TL13 ΤΗΑ26 δ 3.2(3H, s), 6.82(1H, m), 6.9-6.99(5H, m), 7.07(5H, m), 7.16~7.25(8H, m), 7.41~7.44(3H, m), 7.51~7.52(4H, m), 7.59(2H, m) · 665.80 665.20 65 TL13 ΤΗΑ21 δ = 3.2(3H, s), m). 7.16~7.25(8H, m), 7.26(2H, s), 7.41-7.44(3H, m), 7.51-7.52(4H. m), 7.59(2H, m) 625.74 625.18 6β TL13 TF17 δ = 2.26(6H, 3). 3.2(3H, s), 5(1H, 8), 6.9~€.97(5H, m), 7.16~7.25(8H, m), 7.41(1H, m), 7.51~7.56(7H, 674.89 674.28 44 95143 201204807 m), 7·63~7·64(3Η, m), 7.71-7J7(2H, m)· 7.87-7.93(2H, m) 67 TL13 TF15 δ = 3.2(6H, s), 6.53(1H, m), 6.82-6.99(1 OH, m), 7.16~7.34(10H, m), 7.41(1H, m). 7.51~7.56(6H, m). 7.64(2H, m) 672.88 672.26 68 TL14 TAR9 δ « 2.B8(4Hf m). 3.2(3H, s), 6.55(1H( m), 6.72(2H, m), 6.81(1H, m). 6.95(2H, m), 7.05~7.13(3H, m), 7.25(4H, m), 7.39-7.41 (9H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.91(8H, m) 816.04 815.36 69 TL14 TAR18 δ = 2.88(4H, m), 3.2(3H, s). 6.55(1 H, m). 6.72(2H, m). 6.81 (1H, m), 6.95(2H, m), 7.05-7.13(3H, m), 7.25(4H, m). 7.41(1H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.82~7.98{4H, m), 8.12(2H, m), 8.93(1 H.m). 9.09(1 H, m) 639.82 639.29 70 TL14 THA4 δ β 2·88(4Η, m), 3·2(3Η· s), 6·55(1Η· m), 6·72(1Η, m), 6.81(1H, m), 6.95-7.13{5H, m), 7.25(4H, m), 7.41-7.44(3H, m), 7.51-7.52(4H( m), 7.59(2H, m), 7.91(1H,m)f 8.7(1H,s) 542.67 542.25 71 TL14 THA18 δ = 2·88(4Η, m>· 3.2(3H· s>, 6.55(1H, m), 6·72(2Η· m), 6.81(1H, m), 6.95(2H, m), 7.05-7.13(3H, m), 7.25(4H, m), 7.41-7.42(2H, m), 7.51-7.56(6H, m), 7.64{2H( m), 7J7(1H, m), 9.23(1H, s) 596.78 596.23 72 TL14 THA19 δ = 2.88(4H, m). 3.2(3H, s), 6.55(1 H, m), 6.72(1 H, m), 6.81 (1H, m), 6.95~7.13(6H, m), 7^5(5H, s), 7.25(0H, m), 7.41-7.44(3H, m), 7.47(1 H, s), 7.51~7.52(4H, m), 7.59(2H, m) 601.82 601.19 73 TL14 TF3 δ = 1.4(8HP m), 1.48(12H, m), 2.19(2H, m), 2.88(4H, m), 3.2(3H, s), 6.55(1 H, m), 6.72(2H, m), 6.81(1H, m), 6.95(2H, m), 7.05-7.13(3H, m), 725(4H, m). 7.41(1 H, m), λ51~7.56(7Η, m), 7·63~7.64(3Η· m), 7.71-7·77(2Η, m), 7.87~7.93(2H· m) 792.10 791.45 45 95143 201204807 74 TL14 TF19 δ = 0·21(9Η· s), 2·88(4Η· m). 3.2(3H· s), 3·9(1Η· s), 6·55(1Η，m), 6·72(2Η· m), 6·81(1Η· m>, 6·95(2Η, m), 7·05-7·13(3Η· m), 7.25(4Η, m)· 7·41(1Η· m), 7.51-7·56(7Η, m), 7.63-7·64(3Η, m). 7·71-7·77(2Η, m), 7.87-7.93(2Η, m) 700.00 699.33 75 TL15 TAR2 δ = 3.2(3Η, s), 6.6(1 Η, m), 6.77(1 Η, m), 6.86(1 Η, m), 6.95-β.99(5Η, m), 7.08(1 Η, m), 7.25-7.34(6Η, m), 7.41(1 Η, m). 7.51~7.56(8Η, m), 7.64(2Η, m), 7.93-7.96(3Η, m), 8.55(1 Η, m) 587.75 587.26 7$ TL15 TAR12 δ = 3.2(3Η· s), 6.6(1Η· m)· 6·77(1Η, m), 6·86(1Η· m)f 6.95-6.99(5Η, m), 7.08(1Η, m), 7.19-7,34(7Η( m), 7.41(1Η, m), 7.48-7.64(11 Η, m), 7.74-7.79(2Η# m), 7·9(2Η, m) 661.83 661.28 77 TL15 THA5 δ = 3.2(3Η, s)· 6.6(1Η· m), 6·77(1Η，m)· 6·86(1Η· m)· 6·95-6·99(5Η· m), 7·0Β(1Η, m), 7,25-7·34(6Η· m)· 7·41(1ΗΙ· m), 7·51-7.66(10Η· m), Β.21(1Η, m)· 8.38(1 Η, m), 8.83(1 Η, m) 588.74 588.26 78 TL15 THA11 δ = 3.2(3hj, s>, 6·41(1Η· m), 6.6(1Η，m)· 6·7(1Η· m). β.77-6.85(3Ηρ m), 6.99(2Η, m), 7.08(1 Η, m)t 7·14(1Η_ s>_ 7,23-7·28(6Η· m). 7.4W.44(3H, m), 7.48(1H, s), 7.51-7.52(4Ht m), 7.59(2H, m) 590.61 591.15 79 TL15 TY3 δ = 3.2(3H, s), 6.6(1H, m), 6.77(1H, m), 6.86(1H, m), 6.95-6.99(5H, m), 7.08(1H, m), 7.25-7.45(13H, m), 7.48(2H, s), 7.51-7.64(1 OH, m) 742.81 743.21 BO TL15 TY4 δ = 3.2(3H, s), 6.6(1 H, m), 6.77(1 H, m), 6.86(1 H, m), 6.95~6.99{5H, m). 7.08(1 H, m), 7.25-7.34(8H, m), 7.41(1H, m). 7·51-7·56(8Η, m), 7.64<2H· m), 7.79-7.85(4Ht m) 681.82 681.28 81 TL15 TF6 δ = 1.51(4H, m), 2.09(4H, m), 3.2(3H, s), 6.6(1H, m), 6.77(1H, m), 6.86(1H, m),· 6.95-6.99(5H, m), 7.08(1 H, m), 7.25-7.34(6H, m), 7.41 (1H, m), 7.51-7.56(7H, m), 7.63^-7.β4(3Η, m), 7.71-7.77(2H, m), 7.87-7.93(2H, m) 679.89 679.32 82 TL1S TF11 δ = 3^(6H, 3), 6.49(1 H, m), 6.6(1 H, m). 6.77-6.92(1 OH. m), 7.07-7.13(3H, m), 7.25~7.34(6H, m), 7.41(1H, m), 7.51-7.56(6H, m), 656.81 656.28 46 95143 201204807 7·64(2Η· m) 83 TL16 TARS δ = 32(3Η, s), 6.57(1 Η, m), 6.66(1 Η, m), 6.83(1 Η, m), 6.92-6.95(3Η, m), 7_19~7.25<5Η, m), 7.41(1Η_ m), 7.47(2Η. m), 7.51-7.56(12Η, m), 7.85{2Η, m), 7.91-7.97(2Η, m), 8.07(1Η, m), 8.13(1Η, m), 8.31 (2Η, m) 687.87 687.29 β4 TL16 TAR15 δ =» 32(3Κ, S), 6.57(1 Η, m), 6.66(1 Η. m), 6.83(1 Η. m). 6.92-6.95(3Η, m), 7.19-7.25(5Η, m), 7.41-7.52(13Η, m). 7.71 (2Η, m), 7.85-7.88(3Η, m), 8.04(1Η, m), 8.1(1ΗΡ m). 8.28(1Η, m), 8.34(1Η, m), 8.93(2Η, m), 8.99(1 Η, m) 737.93 737.31 85 TL16 THA8 δ = 3.2(3Η, 3). 6.57(1 Η, m), 6.66(1 Η, m), 6.83(1 Η. m), 6.92(1Η, m), 7.19~7.25(6Η, m). 7.37(1Η, m), 7.41(1 Η, m), 7.44(2Η, m), 7.47-7.56(12Η, m), 7.85~7.9(3Η, m), 8.24(1 Η, m), 8.38(1 Η, m), 8.83(1 Η, m) 689.84 689.28 86 TL16 THA14 δ = 3.2(3Η, s), 5.67(1Η, m), 6.66(1 Η, m), 6.79-β.83(2Η, m). 7.06(1 Η, m), 7.19-7.25(6Η, m), 7.41~7.51(13Η, m), 7.85(2Η, m) 642.65 643.15 87 TL16 THA24 δ = 3.2(3Η, β), 6.47(1 Η, m), 6.66(1 Η. m), 6.7fr-6.85(4H, m). 7.14(3Η, s), 7.19-7.25(5Η, m), 7.41~7.47(5Η, m), 7.48(1Η, s), 7.51~7.59(8Η, m), 7.85(2Η, m) 769.69 771.09 的 TL16 THA20 δ = 3·2(3Η· s), 6·66(1Η, m), 6·83(1Η. m). 6.92-6.99(3Η, m), 7.17~7.25(6Η, m). 7.26(2Η, s), 7.41~7.51(13Η, m), 7.85(2Η, m) 669.77 669.24 89 TL16 TFM δ = 3.2(3Η, $), 3.82(3Η, s), 6.57(1Η, m), 6.66(1Η, m), 6.83(1Η, m), 6.92~6.95(3Η, m), 7.17~7.25(6Η, m), 7.33(1Η, m), 7.41(1 Η, m), 7-47-7.56(13Η, m), 7.79-7.85{3H, m), 8.05(1H, m), 8.18(1H, m) 690.87 690.30 90 TL16 TF14 δ = 2.88(4H, m), 3.2(6H, s), 6.48(1H, m), 6.57(1 H, m), 6.6&-6.72(2H, m), 6.81-€.83(2H, m), 6.92-6.95(3H, m), 7.07-7.13(3H, m), 7.19-7.25(5H, m). 7.41~7.52(13H, m), 7.85(2H, m) 718.92 718.33 [實施例1-11]使用本發明之有機電場發光化合物之OLED 裝置之製造 使用本發明之有機電場發光化合物製造了 0LED裝置。 47 95143 201204807 首先，由用於0LED之玻璃（由Samsung Corning製造）取得 之透明電極ΙΤ0薄膜（15Ω/ΙΙΙ)進行超音波清洗（依序使用 三氯乙烯、丙酮、乙醇與蒸餾水清洗），並在使用前儲存於 異丙醇中。之後，將ΙΤ0基板裝設於真空氣相沈積裝置之 基板夾中，將4,4’，4”-三（N，N-(2-萘基）-苯基胺基）三苯 基胺（2-TNATA)置於真空氣相沈積裝置之一槽（cell)中，抽 真空至腔室真空度為1(Γ6托（torr)。之後，施加電流至該 槽中，以蒸發2-TNATA，因而於ΙΤ0基板上形成厚度60nm 之電洞注入層。 之後，將N，Ν’-雙（α-萘基）-Ν，Ν’-二苯基-4, 4’-二胺 (ΝΡΒ)置於真空氣相沈積裝置之另一槽中，施加電流至該槽 中，以蒸發ΝΡΒ ’因而於電洞注入層上形成厚度20 nm之 電洞傳輸層。 形成電洞注入層與電洞傳輸層之後，依下列步驟將電 場發光層形成於其上。將DNA(實施例1至4)、H-36(實施 例8至11)或H-38(範例5至7)置於真空氣相沈積裝置之 一槽中作為主體’而本發明之有機電場發光化合物則置於 另一槽中，作為摻雜劑。該二材料係以1〇〇:1之比例進行 氣相沈積，於電洞傳輸層上形成厚度30 nm之電場發光層。 48 95143 20120480737 95143 201204807 Table 1 Compound LY Ή NMR (CDCb, 200 MHz) MS/FAB Measured value 1 TL1 TAR1 δ « 6.95(2Ht m), 7.25-7.33(7Ht m), 7.41 (1H, m)( 7· 5-7·5β(9Η, m), 7.62~7·64(5Η·m), 7.94(1 H, m), 8.12(1H( m)t 8.55(1H, m) 497.6 497.2 2 TL1 TAR6 δ = 6.95(2H, m), 7.25-7.33(7H, m), 7.41 (1H, m), 7.5-7.56(9H, m), 7.63-7.68(7H, m), 7.79(2H, m), 7.94( 1H, m), 8.12(1H, m), 8.55(1H, m) 5737 573.2 3 TL1 TAR11 δ = 6.95(2H, m), 7.25-7.41 (12H, m), 7.5~7.56(11H.m), 7.63~7.66(4H, m), 7.91-7.96(9H, m), 8.08-8.12(2H.m). 8.55(3H, m) 850.1 849.3 4 TL1 TAR16 δ = 6.95(2Ht m), 7.25-7.41 ( 13H, m), 7.5~7.56(8H, m), 7.63~7.64(3H, m), 7·^>7.94{5Η· m). 8.12(1H, m), 8.55(1 H. m) 671.8 671.3 5 TL1 TAR20 δ = 6.95(2H, m), 7.25-7.33(7H.m), 7.41(1H, m), 7.5-7.56(7Hf m), 7.63~7.64(3H, m), 7.7-7J1( 4H, m), 7.8(1H, m)f 7.9-8(3H, m>, 8.1-8.12(2Hf m), 8.55(1H, m) 621.8 621.2 6 TL1 THAI δ = 6.95(2H, m), 7.25 -7.33(7H, m). 7.41-7.52(8H, m), 7.59-7.63(3H, m), 7.77(1 H, m), 7.9-7.94(2H, m), 8.12( 1H, m), 8.36(1 H, m), 8.55(1 H, m) 498.6 498.2 7 TL1 THA10 δ = 6.95-€.99(2H, m), 7.25-7.35(9H, m), 7.41~7.52 (8H, m), 7.59-7.63(3H, m), 7.94(1 H, m), 8.12(1H,m), 8.55(1H, m) 503,7 503.2 8 TL1 THA7 δ = 6.95(2H. m ), 7.25-7.33(8H, m). 7.41 (1H.m). 7.5~7.56(7H.m), 7.63-7.64(3H, m), 7.83(1 H, m). 7.94(1 H, m ), 8.12(1 H, m), 8.55(1 H. m), 8.7(2H, m) 549.7 549.2 9 TL1 TY2 δ = 6.95(2H, m), 7.25~7.33(7rt, m), 7.41 (1H , m), 7.5~7.5β(9Η, m), 7.63-7.79(11H.m), 7.94(1H, m), 8.12(1H,m), 855{1H,m) 655.8 655.2 10 TL1 THA26 δ = 6.54(1 H. m), 6.82(1 H, m), 6.95~B.99(2H, m), 7.07(4H, m), 7.25-7.33(7H, m), 7.41~7.52(8H, m ), 7.59-7.63(3H, m), 7.94(1 H, m), 8.12(1 H, m), 6197 619.2 38 95143 201204807 8.55(1 H, m) 11 TL1 TY7 δ = 6.95(2Ht m), 7.25(7H( s), 7.25-7.33(2H, m), 7.41(1H, m), 7·5-7.56<9Η, m), 7,63~7.68(5H,m), 7·79( 4Η· m), 7_94(1H, 8.12(1H, m>· 8_55(1H. m) 711.9 711.2 12 TL1 THA21 δ = 6.95-6.99(2H, m), 7^5(5H, m), 7.26{2H , s), 7.29~7.33(2H, m), 7.41~7.52(8H, m), 7. 59-7.63(3H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m) 579.6 579.2 13 TL1 TF5 δ « 1.48(6H, m), 2.02(4Ht m). 6.95 (2H, m), 7.17(1H, m), 7.25-7.34(9H, m). 7.41(1H, m), 7.5-7.56(8H, m), 7.63-7.64(3H, m), 7.87(2H , m), 7.94(1Ht m). 8.12(1H, m), 8.55(1^ m) 653.9 653.3 14 TL1 TF17 δ = 2.26(6H, s), 5{1H, s), 6.95(2H, m) , 7.17(1 H, m), 7.25-7.34(9H, m), 7.41(1 H, m), 7.5~7.56(8H, m), 7.63-7.64(3H, m), 7.87(2H, m) , 7.94(1H, m), 8.12(1H, m), 8.55(1H,m) 628.8 628.3 15 TL1 7F10 δ = 3.2(3H, s), 3.81(2H, s), 6.41(1H, m), 6.49 (1 H, m), 6.56(1 H, m); 6.95-7.03(5H, m), 7.25-7.33{7H, m), 7.41(1 H, m), 7.5-7.56(7H, m). 7.63-7·64(3Η.m), 7.94(1 H, m), 8.12(1 H. m), 8.55(1 H, m) 614.8 614.3 16 TL1 TF15 δ = 3.2(3H, s), 6.61 ( 1H, m), 6.86(1 H. m), 6.94~6.99(4H, m), 7.25-7.34(13H, m), 7.41 (1H, m), 7.5~7.52(5H, m). 7.63(^ , m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m) 600.7 600.3 17 TL2 TAR4 δ = 3.81(2H, s), 6.51(2H, m), 6.69(2H, m ), 6.9 &-7.01(6H, m). 7.25(4H, m), 7.38-7.41 (5H, m), 7.51-7.56 (6H, m), 7.64(2H, m), 7.88-7.9(4H, m) 611.8 611.3 18 TL2 TAR9 δ = 3.81 (2H, s), 6.51 (2H, m), 6.69(2H, m), 6.95~7.01 ( 6H, m). 7.25(4H, m), 7.38-7.41 (9H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.88-7.91 (8H, m) 788.0 787.3 19 TL4 TAR14 δ = 6.59(2H, m), 6.77(2H, m), 6.89(2H, m), 6.91 (1H, s), 6.92-6.95(^, m), 7.25(4H, m), 7.41 (1H. m), 7.51-7.56(6H.m), 7.64(2H, m), 7.82-7.88(4H.m), 8.12(2H, m), 8.93(2H, m), 9.09(1H, s) 663.8 663.3 39 95143 201204807 20 TL4 TAR18 δ = 6.59(2Η, m), 6.77(2Η, m), β.89-6.95(7Η, m), 7·25(4Η, m), 7.41(1Η, m), 7.51 - 7.56(6Η, m). 7.64(2Η, m), 7.82-7.88(2Η, m), 7.98(1 Η, m), 8.12(2Η, m). 8·93(1Η, m), 9.09( 1Η, m) 613.7 613.2 21 TL5 THA29 δ = 6; 95~6.97(4Η, m), 7.12-7.25(11 Η. m). 7.4W.44(3H, m). 7.51 ~7.52(4Η. m) , 7.59(2Η, m), 7.72(1 Η, m), 7.83(1 Η, m), 8.25(1 Η, m), 8.5(1 Η, m), 8.97(1Η, m) 631.8 631.2 22 TL5 THM δ A 6.95~6.99 (4Η, m), 7.16-7.25(10Η. m), 7.41~7.44(3Η, m), 7.51-7.52(4Η, m), 7.59(2Η, m), 8.25(1 Η , s) 532.7 532.2 23 TL6 THA13 δ = 2.88(4Ht m)f 6.58(2Ht m), 6.76(2H(m), 6.95-7.04(6Ht m), 7.25{4H, m). 7.41-7.44(3H, m). 7.51-7.52 (4H(m), 7.59(2H, m) 533.7 533.2 24 TL6 THA18 δ 〇2.88(4H, m). 6.58(2H, m), 6.73-6.76(3Ht m), 6.95(2H, m), 7.02- 7.04(4H, m), 7.11(1H, m), 7·25(4Η, m), 7.41(1H, m}. 7.51-7.56(6H, m), 7.64(2H, m), 9.23(1 H , S) Λ 582.8 582.2 25 TL6 THA25 δ = 2.88(4H, m), 6.3(1 H, m), 6.58(2H, m), 6.76(2H, m). 6.95-7.04(6H, m), 7.25 -7.28(5H, m), 7.35(1 H, m), 7.41-7.44(3H, m), 7.51-7.52(4H, m), 7.59(2H, m), 7.73(3H, m) 696.0 695.2 26 TL7 TY4 δ * 6.63(2H, m), 6.69(2H, m), 6.81 (2H, m), 6.95-7!〇5(6H, m). 7.25(6H. m), 7.41(1 H. m ), 7.51~7.56(10H, m), 7.64(2H, m), 7.79(2H, m) 667.8 667.3 27 TL7 TF1 δ = 6.58-6.63(3H, m), β.75-6.81(3Η, m) , 6.95-7.05(6H.m), 7.11(4H, m), 7.25~7.26(8H, m), 7.33(4H, m), 7.41(1 H, m), 7.51-7.56(7H, m), 7.62-7.64(3H, m), 7.71 (1H, m), 7.87(1 H, m) 764.0 1 763.3 28 TL7 TF6 δ * 1.51(4H, m), 2.09(4H, m), -6.58-6.63 ( 3H, m), 6.75-6.81 (3H, m), 6.95-7.05 (6H. m), 7.25(6H, m). 7.41(1H, m), 7.51-7.56(7H, m). 7.62-7.64(3H, m), 7.71(1H,m), 7.87(1H, m) 665.9 665.3 29 TL7 TF18 δ = 5(1 H, s), 6.58~6.63(3H, m), 6.75-6.81 (5H, m), 6.95-7.05(6H, m), 7.23-7.25(1 OH, m). 7.33{4H , m), 779.0 778.3 40 95143 201204807 7.41(1Η· m)· 7·51-7·56(7Η, m), 7·62-7.64(3Η· m), 7.71(1Η, m), 7.87(1Hlm 30 TL7 TF11 δ = 3.2(3Η, s), 5.7(1 Η, m), 5.91(1 Η, m), 6.49(1 Η.m), 6.63-6.67(3Η, m), 6.81(2Η, m), 6.92~7.05(7Η, m), 7.13(1 Η, m), 7.25(6Η, m), 7.41(1 Η, m), 7.51-7.56(6^ m), 7.64(2Η, m) 642·β 642.3 31 TL8 THA27 δ = 6·59(1Η· s), 6·69(2Η· m)· 6·81-6.87(4Η· m). 7.1^, s)t 7.16(2Η· m) , 7·25(4Η, m), 7.41-7.59(13Η, m), 7.85(2Η, m) 884.7 887.0 32 TL8 TY5 δ = 6.69(4Η, m), 6.87(2Η, m), 6.95(2Η, m), 7.16(2Η, m), 7.25(4Η, m), 7.41-7.56(13Η, m), 7.64(2Η, m), 7.76~7.85(6Η. m) 733-9 733.3 33 TL8 TF2 δ = 6.58(1Η, m), 6.69~6.75(3H, m). 6.87(2Η, m), 6.95(2Ηι m), 7.16-7.25(10Η_ m), 7.35(2Η, m), 7.41-7.56(12Η, m), 7.62~7.64 (3Η , m), 7.71-7J5(3H, m), 7.85-7.87(3Η, m) 812.0 811.3 34 TL8 TF7 δ = 3.49(4Η, s), 6.58(1Η, m), 6·69~6.75(3Η, m>, 6.87(2Η, m), 6.95(2Η, m), 7.16-7.25(10Η, m), 7.41~7.56(12Η, m), 7.62-7.64(3Η, m), 7.71(1Η, m) 7.85-7.87(3Ht m) 764.0 763.3 35 TL8 TF13 δ = 3.2(3Η, m), 5.88(1 Η, m), 6.47(1 Η, m), 6.69(2Η, m), 6.87-6.97(5Η , m), 7.16-7.25(11 Η, m), 7.41~7.54{9Η, m), 7.85(2Η, m) 682.9 682.2 36 TL8 TF16 δ = 3.2(3Η, m), 5.8(1Η, m), 6.01(1Η, m), 6.57(1Η, m), 6.69(2Η, m)t 6.87~β.92(3Η, rr〇, 7·16(2Η, m), 7^5(8Η, m), 7.32(1Η, m), 7.41-7.54(11 Η, m). 7.63(1 Η, m), 7.85(4Η, m) 726.9 726.3 37 TL9 TAR7 δ = 3.82(3Η, s), 6.95(2Η, m ), 7.25(12Η, m), 7.41~7.42(3Η.m). 7.51~7.64(14Η, m), 7.79(1Η, m), 8.17-8.18(2Η, m) 663.85 663.29 38 TL9 TAR17 δ = 3.82 {3Η, s). 6.95(2Η, m), 7i5(4H, m), 7.41~7.42(3Η, m). 7.51~7.64(10Η, m), 7.71 (2Η, m), 7·79{1Η · m), 7·98-8·04(2Η, m), 8.12-8·18(4Η, m), 9.09(1 Η, m), 9.15(1 Η, m) 611.77 611.26 41 95143 201204807 39 TL9 THA2 δ = 3.82 (3Η, s), 7.2~7.25(5Η, m), 7.41(1Η, m). 7.42-7.51 (14Η, m), 7.79-7.83(2Η, m). 8.17-8.18( 2Η, m), 8.85(1 Η, m) 512-64 512.23 40 TL9 THA15 δ = 3·82(3Η, s>, 6·95-6·99(2Η· 7·25(4Η, m)· 7.41 -7.44(5Η, m). 7.51-7.52(4Η, m), 7.59-7.62(4Η, m), 7.79(1Η, m), 8.17-8.18(2H, m), 8.63(2Η, m) 569.72 569.19 41 TL9 THA25 δ = 3.82 (3Η, 6), 6.95~6.99(2Η, m), 7.25{4Η, m), 7.35(1Η, m), 7.41-7.44(5Η, m), 7.51-7.52(4Η, m), 7.59-7.62(4Η, m). 7.73~7.79(6Η, m), 8.17~8.18(2Η, m) 681.93 681.16 42 TL9 TF1 δ =. 3.82(3Η, s), 6.95(2Η, m) , 7.11(4Η, m). 7.25~7.26(6Η, m), 7.33(4Η, m), 7.41-7.42(3Η. m), 7.51-7.56(12Η, m), 7.71-7.79(3Η, m) 7.87~7.93(2Η, m), 8.17-8.18(2Η, m) 751.95 751.32 43 TL9 TF1B /,·· δ = 3.82(3Η, 3), 5(1 Η, s)( 6J7(2H, m) ( 6.95(2Η, τη), 7.23-7.25(8Η, τη), 7.33(4Η, m), 7.41-7.42(3Η, m), 7.51-7.56(12Η, m), 7·71-7·79( 3Η, m), 7.87~7.93(2Ht m)( 8.17-8.18(2Η, m) 766.97 766.33 44 TL9 TF16 δ = 3·2(3Η, s), 3·82(3Η, s ). 6,57-6.59(2Η, m〉, 6·88^6·95(4Η, m), 7·25(4Η, m)· 7.41(1 Η· m)· 7.42(2Η, m), 7.47 (2Η(m), 7.51-7.57(12Η, m), 7·79-7·85(3Η·m), 8·17-8·18(2Η· m) 690.87 690.30 45 TL10 TAR10 δ = 1.72( 6Η, s), 3.2(3Η, s), 6.52(1 Η, m), β.69(2Η, m), 6.78(1Η, m), 6.95(2Η, m), 7.05-7.14{3Η. m ), 7.25(8Η, m), 7.39~7.41(5Η, m). 7.51-7.56(8Η, m), 7.64(4Η, m), 7.91 (4Η, m) 806.04 805.37 46 TL10 TAR19 δ = 1.72(6Η , s), 3.2(3Η, s), 6.52(1Η, m), 6.69ί2Η, m), 6.78〇H, m), 6.95{2Η, m), 7.05-7.14(3Η, m), 7.25(4Η , m), 7.41(1Η, m), 7.51-7.56(6Η, m), 7.64(2Η, m), 7.71(2Η, m), 7·β2-7.88(3Η, m), 8.04(1Η, m ), 8.12(1Η, m), 8.18(1Η, m) 677.87 677.31 47 TL10 THA9 δ = 1.72(6Η, s), 3.2(3Η, s), 6.52(1 Η, m), 6.69(1 Η, m ), 6.78-6.82 (2Η, m), 6.95~7.14(7Η, m), 7.25(4Η, m), 7.41~7.44(3Η, m), 7.51-7.52(4Η, m), 7.59(2Η. m) ) 543.70 543.26 42 95143 201204807 48 TL10 TY1 δ = 1.72(6H, s), 3·2(3Η, s), 6·52“1Η, m), 6·69(2Η, m)f 6.78(1H( m ), 6.95{2H, m), 7.05-7.14 (5 H, m), 7.25(6H, m)· 7.41(1H·m>, 7.5W.56(8H.m), 7·64(2Η·m>, 7·85(2Η,m), 7.95 (2Η, m) 695.89 695.32 49 TL10 THA28 δ = 0.14(6H, s), 1.72(6H, s), 3.2(3H, s), 6.52(1 H, m), 6.69(1 H. m), 6.78 (1 H, m), 6.95-7.03 (3H, m). 7.04(2H, S), 7.05-7.14(4H, m), 7.25(4H, m). 7.35(2H, m), 7.41-7.44 ( 3H, m), 7.51-7.52(4H, m), 7.59(2H,m), 7.89(1 H,m) 750.10 749.26 50 TL10 TF4 δ = 1.72(6Η, s), 32(3H, s)( 6.52 (1H# m)( 6.69(2H, m)· 6·78^.81(3Η· m), 6·95(2Η·.πι), 7·05-7·14 “3Η· m), 7, 25(4H, m). 7·41(1Η, m), 7,48~7·56<9Η, m), 7.63-7.64(3^m), 7 J1-7.77(2H, m), 7.87- 7.93{2H(m), 8·51(2Η.m) 793.99 793,35 51 *;· TL10 TF9 δ = 0.66(6H, s), 1.72(6H, s), 3.2(3H, s), 6.52( 1 H, m), 6.69 (2H, m), 6.78 (1 H, m), 6.95 (2H, m), 7.05-7.1^, m), 7.25 (4H, m), 7.35 (1H, m), 7.41 (1H, m), 7.51-7.56(6H, m), 7.64~7.66{3HP m), 7.76(1 H, m), 7.82(1 H, m), 7.89(1 H, m), 7.95( 1 H, m) 685.97 685.32 52 TL12 TAR3 δ = 3.2(3H, s), 6.56(1 H, m), 6.73(1 H, m), 6.82(1 H, m). 6.92-6.98(5H, m ), 7 .07(1 H, m), 7.25(4H, m). 7.41 (1H, m), 7.51-7.64(10H, m), 7.73(1 H, m), 7.8(1 H, m). 7.92- 7.95(2H, m) 577.71 577.24 53 TL12 TAR13 δ = 3.2(3H, s), 6.56(1H, m), 6.73{1H, m). 6.82(1H, m), 6.92-6.98(5H, m), 7.7(1 H. m). 7.25(4H, m), 7.41(1 H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.82-7.88(2H, m), 7.98- 8.04(2H, m), 8.12(2H, m), 8.18(1H, m), 8.93(1H, m), 9.09(1H, m), 9.15(1H, m) 677.83 677.27 54 TL12 THA6 δ = 3^ (3H, s), 6.56(1 H, m), 6.73(1 H, m), 6.82(1 H, m). 6.92-6.98(5H.m), 7.07(1 H, m), 7.25(4H · m), 7.41-7.44(3H, m), 7.51~7.52(4H, m), 7.59(2H, m), 8.03(1 H, m). 8.12(1 H, m). 8.27(1H, m ), 8.5(^, m), 8.97(1 Hm) 578.70 578.24 55 TL12 THA12 δ = 3.2(3H, s), 6.56(1H, m), 6.73(1H. m). 6.82(1H, m). 6.92 -6.99(5H, m), 7.25(4H, m), 7.41~7.44(4H, m), 7.51-7.52(4H, m), 7.59(2H, m) 519.59 519.19 43 95143 201204807 56 TL12 ΤΗΑ22 δ = 3.2 (3Η, s), 6.56(1 Η, m), 6.73(1 Η, m). 6.82(1 Η, m), 6.92-6.99(5Η, m), 7.07(1 Η, m), 7.25(4Η , m), 7.35(1Η, m). 7.41-7.44(3Η, m), 7.51-7.52(4Η, m), 7.59(2Η, m), 7.73(3Η, m) 615.81 615.17 57 TL12 ΤΥ5 δ = 3.2(3H, s), 6.56(1Η, m), 6.73(1Η, m)· 6.82(1Η, m)( 6.92-6.98(5Η, m), 7.07(1Η, m), 7.25(6Η, m), 7.41(1Η, m)( 7.51-7.56(8Η, m), 7.64(2Η. m), 7.79-7.85( 4Η, m) 687.85 687.23 58 TL12 TF7 δ = 3·2(3Η· s), 3.49(4Η· s), 6.56(1Η, m)· 6,73(1Η· m), 6·82<1Η, m 6·92-β·98(5Η·m>, 7.07 “1Η, m>· 7.2-7.25(8Η, m), 7.41(1Η, m), 7.51-7.56(7Η, m), 7.63-7.64 (3Η, ητ〇· 7·71-7·77(2Η, m), 7.87-7·93(2Η, m) 717.89 717.30 59 TL12 TF12 δ = 3.2(6Η, s), 6.53-β.5β(2Η , m), 6.73(1 Η, m), 6.82~6.98(8Η, mj, 7.07-7.11(2Η, m), 7.22-7.28(6Η, m), 7.41(1 Η, m), 7.51-7.56( 6Η, m), 7.64(2Η, m) 709.73 710.18 60 TL13 TAR6 δ =* 3,2(3Η, 8), 6.9~6.97{5Η, m), 7.1β-7.25(12Η, m), 7.41(1 Η, m), 7.51-7.56(8Η, m), 7.64(4Η, m) 619.82 619.23 61 TL13 TAR16 δ = 3.2(3Η, s), 6.9~6.97(5Η. m), 7.16-7.25(8Η, m ), 7.39-7.41 (5Η, m), 7.51-7.64(1 OH, m), 7.91-7.97(4H.m) 717.92 717,25 62 TL13 THAI 6 = 35(3H, s), 6.95-6.97(3H, m). 7.16-7.25(8H, m), 7.41-7.52(1 OH, m), 7.59(2H, m), 7.97(1 H, m), 8.33(1 H , m) 544.71 544.20 63 TL13 ΤΗΑ7 δ = 3.2(3H, s), 6.9-6.97(5H, m), 7.16-7.25(8H, m), 7.41 (1H, m), 7.51~7.56(6H, m) , 7.64(2HP m), 7.9(2H, m), 8.74(2H, m) 595.75 595.21 64 TL13 ΤΗΑ26 δ 3.2(3H, s), 6.82(1H, m), 6.9-6.99(5H, m), 7.07 (5H, m), 7.16~7.25(8H, m), 7.41~7.44(3H, m), 7.51~7.52(4H, m), 7.59(2H, m) · 665.80 665.20 65 TL13 ΤΗΑ21 δ = 3.2(3H , s), m). 7.16~7.25(8H, m), 7.26(2H, s), 7.41-7.44(3H, m), 7.51-7.52(4H.m), 7.59(2H, m) 625.74 625.18 6β TL13 TF17 δ = 2.26(6H, 3). 3.2(3H, s), 5(1H, 8), 6.9~€.97(5H, m), 7.16~7.25(8H, m), 7.41(1H, m ), 7.51~7.56(7H, 674.89 674.28 44 95143 201204807 m), 7·63~7·64(3Η, m), 7.71-7J7(2H, m)· 7.87-7.93(2H, m) 67 TL13 TF15 δ = 3.2(6H, s), 6.53(1H, m), 6.82-6.99(1 OH, m), 7.16~7.34(10H, m), 7.41(1H, m). 7.51~7.56(6H, m). 7.64(2H, m) 672.88 672.26 68 TL14 TAR9 δ « 2.B8(4Hf m). 3.2(3H, s), 6.55(1H( m), 6.72(2H, m), 6.81(1H, m). 6.95 (2H, m), 7.05~7.13(3H, m), 7.25(4H, m), 7.39-7.41 (9H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.91(8H , m) 816.04 815.36 69 TL14 TAR18 δ = 2.88(4H, m), 3.2(3H, s). 6.55(1 H, m). 6.72(2H, m). 6.81 (1H, m), 6.95(2H, m), 7.05-7.13(3H, m), 7.25(4H, m). 7.41(1H, m), 7.51-7.56(6H, m), 7.64(2H, m), 7.82~7.98{4H, m) , 8.12(2H, m), 8.93(1 Hm). 9.09(1 H, m) 639.82 639.29 70 TL14 THA4 δ β 2·88(4Η, m), 3·2(3Η· s), 6·55( 1Η· m), 6·72(1Η, m), 6.81(1H, m), 6.95-7.13{5H, m), 7.25(4H, m), 7.41-7.44(3H, m), 7.51-7.52( 4H(m), 7.59(2H, m), 7.91(1H,m)f 8.7(1H,s) 542.67 542.25 71 TL14 THA18 δ = 2·88(4Η, m>· 3.2(3H· s>, 6.55( 1H, m), 6·72(2Η·m), 6.81(1H, m), 6.95(2H, m), 7.05-7.13(3H, m), 7.25(4H, m), 7.41-7.42(2H, m), 7.51-7.56(6H, m), 7.64{2H(m), 7J7(1H, m), 9.23(1H, s) 596.78 596.23 72 TL14 THA19 δ = 2.88(4H, m). 3.2(3H, s), 6.55(1 H, m), 6.72(1 H, m), 6.81 (1H, m), 6.95~7.13(6H, m), 7^5(5H, s), 7.25(0H, m) , 7.41-7.44(3H, m), 7.47(1 H, s), 7.51~7.52(4H, m), 7.59(2H, m) 601.82 60 1.19 73 TL14 TF3 δ = 1.4(8HP m), 1.48(12H, m), 2.19(2H, m), 2.88(4H, m), 3.2(3H, s), 6.55(1 H, m), 6.72( 2H, m), 6.81(1H, m), 6.95(2H, m), 7.05-7.13(3H, m), 725(4H, m). 7.41(1 H, m), λ51~7.56(7Η, m ), 7·63~7.64(3Η· m), 7.71-7·77(2Η, m), 7.87~7.93(2H· m) 792.10 791.45 45 95143 201204807 74 TL14 TF19 δ = 0·21(9Η· s) , 2·88(4Η· m). 3.2(3H· s), 3·9(1Η· s), 6·55(1Η,m), 6·72(2Η· m), 6·81(1Η·· m>, 6·95(2Η, m), 7·05-7·13(3Η·m), 7.25(4Η, m)· 7·41(1Η· m), 7.51-7·56(7Η, m ), 7.63-7·64(3Η, m). 7·71-7·77(2Η, m), 7.87-7.93(2Η, m) 700.00 699.33 75 TL15 TAR2 δ = 3.2(3Η, s), 6.6( 1 Η, m), 6.77(1 Η, m), 6.86(1 Η, m), 6.95-β.99(5Η, m), 7.08(1 Η, m), 7.25-7.34(6Η, m), 7.41(1 Η, m). 7.51~7.56(8Η, m), 7.64(2Η, m), 7.93-7.96(3Η, m), 8.55(1 Η, m) 587.75 587.26 7$ TL15 TAR12 δ = 3.2( 3Η· s), 6.6(1Η· m)· 6·77(1Η, m), 6·86(1Η·m)f 6.95-6.99(5Η, m), 7.08(1Η, m), 7.19-7, 34(7Η(m), 7.41(1Η, m), 7.48-7.64(11 Η, m), 7.74-7.79(2Η# m), 7·9 (2Η, m) 661.83 661.28 77 TL15 THA5 δ = 3.2(3Η, s)· 6.6(1Η· m), 6·77(1Η,m)· 6·86(1Η· m)· 6·95-6· 99(5Η· m), 7·0Β(1Η, m), 7,25-7·34(6Η· m)· 7·41(1ΗΙ· m), 7·51-7.66(10Η· m), Β .21(1Η, m)· 8.38(1 Η, m), 8.83(1 Η, m) 588.74 588.26 78 TL15 THA11 δ = 3.2(3hj, s>, 6·41(1Η· m), 6.6(1Η, m)· 6·7(1Η· m). β.77-6.85(3Ηρ m), 6.99(2Η, m), 7.08(1 Η, m)t 7·14(1Η_ s>_ 7,23-7 ·28(6Η· m). 7.4W.44(3H, m), 7.48(1H, s), 7.51-7.52(4Ht m), 7.59(2H, m) 590.61 591.15 79 TL15 TY3 δ = 3.2(3H, s), 6.6(1H, m), 6.77(1H, m), 6.86(1H, m), 6.95-6.99(5H, m), 7.08(1H, m), 7.25-7.45(13H, m), 7.48 (2H, s), 7.51-7.64(1 OH, m) 742.81 743.21 BO TL15 TY4 δ = 3.2(3H, s), 6.6(1 H, m), 6.77(1 H, m), 6.86(1 H, m), 6.95~6.99{5H, m). 7.08(1 H, m), 7.25-7.34(8H, m), 7.41(1H, m). 7·51-7·56(8Η, m), 7.64 <2H·m), 7.79-7.85(4Ht m) 681.82 681.28 81 TL15 TF6 δ = 1.51(4H, m), 2.09(4H, m), 3.2(3H, s), 6.6(1H, m), 6.77 (1H, m), 6.86(1H, m), · 6.95-6.99(5H, m), 7.08(1 H, m) , 7.25-7.34(6H, m), 7.41 (1H, m), 7.51-7.56(7H, m), 7.63^-7.β4(3Η, m), 7.71-7.77(2H, m), 7.87-7.93 (2H, m) 679.89 679.32 82 TL1S TF11 δ = 3^(6H, 3), 6.49(1 H, m), 6.6(1 H, m). 6.77-6.92(1 OH. m), 7.07-7.13( 3H, m), 7.25~7.34(6H, m), 7.41(1H, m), 7.51-7.56(6H, m), 656.81 656.28 46 95143 201204807 7·64(2Η· m) 83 TL16 TARS δ = 32( 3Η, s), 6.57(1 Η, m), 6.66(1 Η, m), 6.83(1 Η, m), 6.92-6.95(3Η, m), 7_19~7.25<5Η, m), 7.41( 1Η_ m), 7.47(2Η. m), 7.51-7.56(12Η, m), 7.85{2Η, m), 7.91-7.97(2Η, m), 8.07(1Η, m), 8.13(1Η, m), 8.31 (2Η, m) 687.87 687.29 β4 TL16 TAR15 δ =» 32(3Κ, S), 6.57(1 Η, m), 6.66(1 Η. m), 6.83(1 Η. m). 6.92-6.95(3Η , m), 7.19-7.25(5Η, m), 7.41-7.52(13Η, m). 7.71 (2Η, m), 7.85-7.88(3Η, m), 8.04(1Η, m), 8.1(1ΗΡ m) 8.28(1Η, m), 8.34(1Η, m), 8.93(2Η, m), 8.99(1 Η, m) 737.93 737.31 85 TL16 THA8 δ = 3.2(3Η, 3). 6.57(1 Η, m) , 6.66(1 Η, m), 6.83(1 Η. m), 6.92(1Η, m), 7.19~7.25(6Η, m). 7.37(1Η, m), 7.41(1 Η, m), 7.44( 2Η, m), 7.47-7. 56(12Η, m), 7.85~7.9(3Η, m), 8.24(1 Η, m), 8.38(1 Η, m), 8.83(1 Η, m) 689.84 689.28 86 TL16 THA14 δ = 3.2(3Η, s), 5.67(1Η, m), 6.66(1 Η, m), 6.79-β.83(2Η, m). 7.06(1 Η, m), 7.19-7.25(6Η, m), 7.41~7.51( 13Η, m), 7.85(2Η, m) 642.65 643.15 87 TL16 THA24 δ = 3.2(3Η, β), 6.47(1 Η, m), 6.66(1 Η. m), 6.7fr-6.85(4H, m) 7.14(3Η, s), 7.19-7.25(5Η, m), 7.41~7.47(5Η, m), 7.48(1Η, s), 7.51~7.59(8Η, m), 7.85(2Η, m) 769.69 771.09 TL16 THA20 δ = 3·2(3Η· s), 6.66(1Η, m), 6·83(1Η. m). 6.92-6.99(3Η, m), 7.17~7.25(6Η, m). 7.26(2Η, s), 7.41~7.51(13Η, m), 7.85(2Η, m) 669.77 669.24 89 TL16 TFM δ = 3.2(3Η, $), 3.82(3Η, s), 6.57(1Η, m), 6.66(1Η, m), 6.83(1Η, m), 6.92~6.95(3Η, m), 7.17~7.25(6Η, m), 7.33(1Η, m), 7.41(1 Η, m), 7-47 -7.56(13Η, m), 7.79-7.85{3H, m), 8.05(1H, m), 8.18(1H, m) 690.87 690.30 90 TL16 TF14 δ = 2.88(4H, m), 3.2(6H, s) , 6.48(1H, m), 6.57(1 H, m), 6.6&-6.72(2H, m), 6.81-€.83(2H, m), 6.92-6.95(3H, m), 7.07-7.13 (3H, m), 7.19-7.2 5(5H, m). 7.41~7.52(13H, m), 7.85(2H, m) 718.92 718.33 [Example 1-11] Manufacture of an OLED device using the organic electroluminescent compound of the present invention using the organic electric field of the present invention The luminescent compound produced an OLED device. 47 95143 201204807 First, the transparent electrode ΙΤ0 film (15 Ω / ΙΙΙ) obtained from the glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned (sequentially washed with trichloroethylene, acetone, ethanol and distilled water), and Store in isopropanol before use. Thereafter, the ΙΤ0 substrate is mounted in a substrate holder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 2-TNATA) is placed in a cell of a vacuum vapor deposition apparatus, and evacuated to a chamber vacuum of 1 (Γ6 torr). Thereafter, a current is applied to the tank to evaporate 2-TNATA. Thus, a hole injecting layer having a thickness of 60 nm is formed on the substrate of ΙΤ0. Thereafter, N, Ν'-bis(α-naphthyl)-fluorene, Ν'-diphenyl-4,4'-diamine (ΝΡΒ) is placed. In another tank of the vacuum vapor deposition apparatus, a current is applied to the tank to evaporate ΝΡΒ', thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Forming a hole injection layer and a hole transport layer Thereafter, an electroluminescent layer is formed thereon by the following steps: DNA (Examples 1 to 4), H-36 (Examples 8 to 11) or H-38 (Examples 5 to 7) are placed in vacuum vapor deposition The organic electroluminescent compound of the present invention is placed in another tank as a dopant. The two materials are vapor deposited at a ratio of 1〇〇:1. The thickness of the electroluminescent layer 30 nm is formed on the transport layer. 4,895,143,201,204,807

DNADNA

之後’將三（8-羥基喹啉）-鋁（III) 雷媼路本爲tL_ V/UQ)氣相沈積於 電％發先層上，作為厚度2〇11111之電子傳 ';^Hr2lithium quinolate, 作為厚度1至2nm之電子注人層，之後使用另一個真空氣 相沈積裝置，形成厚度15〇 nm之A1陰極而製造出〇LED。 用於0LED中之每一種化合物皆於1〇-6 t〇rr下，經真 空昇華器純化。 [比較例1]使用現今電場發光材料之〇LED裝爹之製造 以如同實施例1之相同方法形成電洞注入廣與電洞傳 輸層之後，發出藍光之])^係置於真空氣相沈積裝置之一 槽中作為主體，而化合物A置於另一槽中。該>材料係以 100 : 1之比例進行氣相沈積，於電洞傳輸層上#成厚度 30nm之電場發光層。After that, the tris(8-hydroxyquinoline)-aluminum(III) Thunder Road is tL_V/UQ) was vapor deposited on the electric pre-existing layer as an electron transfer with a thickness of 2〇11111; ^Hr2lithium quinolate As an electron-injecting layer having a thickness of 1 to 2 nm, an A1 cathode having a thickness of 15 〇 nm was formed using another vacuum vapor deposition apparatus to fabricate a ruthenium LED. Each of the compounds used in the OLED was purified by a vacuum sublimator at 1 〇 -6 t rrrr. [Comparative Example 1] Fabrication of a 爹LED device using a current electric field luminescent material After forming a hole injection wide and a hole transport layer in the same manner as in Example 1, a blue light was emitted] One of the devices is in the tank as the main body, and the compound A is placed in the other tank. The material was vapor-deposited at a ratio of 100:1, and an electric field light-emitting layer having a thickness of 30 nm was formed on the hole transport layer.

95143 49 201204807 之後，以如實施例1相同之方式形成電子傳輸層與電 子注入層’之後使用另一個真空氣相沈積裝氣相沉積厚度 150 nm之A1陰極，而製造出0LED。 實施例1至11與比較例1所製造之0LED裝置之發光效 率，係於1，000燭光/平方公尺（cd/m2)測量。結果列於表2。 表295143 49 201204807 Thereafter, an electron transport layer and an electron injection layer ' were formed in the same manner as in Example 1 and then another vacuum vapor deposition was used to vapor-deposit the A1 cathode having a thickness of 150 nm to fabricate an OLED. The luminous efficiencies of the OLED devices manufactured in Examples 1 to 11 and Comparative Example 1 were measured at 1,000 candelas per square meter (cd/m2). The results are shown in Table 2. Table 2

如表2所示，與現有之電場發光化合物相較 之有機電場發光化合物可提供純藍色。去 吸乃 田吊要藍光I至I丨磕 約CIE y=0. 1，以實現接近有機電場發光顯示器之 準時，本發明之有機電場發光化合物可為有 不 述，本發明之有機f場發光化合物可使用 :=所 度之發出藍光材料" 马具有商純 【圖式簡單說明】無 【主要元件符號說明】無 95143 50As shown in Table 2, the organic electroluminescent compound is comparable to the conventional electroluminescent compound to provide a pure blue color. The organic electroluminescent compound of the present invention may be omitted, and the organic f-field luminescent compound of the present invention may be omitted. Can use: = the degree of blue light material " Ma has a commercial pure [schematic description] no [main symbol description] no 95143 50

Claims (1)

201204807 七、申請專利範圍： 1. 一種由化學式1或2表示之有機電場發光化合物： 化學式1201204807 VII. Patent application scope: 1. An organic electric field luminescent compound represented by Chemical Formula 1 or 2: Chemical Formula 1 其中 Ri至Rs獨立地表示氫、（C1-C60)烷基、（C3-C60) 環烷基、（C6-C60)芳基、含有一個或多個雜原子之 (C2-C60)雜芳基（該雜原子選自N、〇、s、p、Si與se)、 (C1-C60)院氧基、（C1-C60)烧基硫基、（C6—C60)芳基氧 基、（C6-C60)芳基硫基、（C6-C30)芳基（C1_C30)烷基胺 基、三（C1-C30)烷基矽基、二（C1-C30)烷基（C6-C30) 芳基矽基、或三（C6-C30)芳基矽基 X 表不化學KCM7L8)、、_Si(R9)(Rl。)-、 、_s—、_Se-、或-(Rn)C=C(R12)〜； r6至r12獨立地表示氫、⑻，）烧基、（c3_c6〇) 環烧基、⑽-⑽芳基、含有一個或多個雜原子之 (C2—C6G)雜方基（該雜原子選自N、〇、s、Si與Se)、 95143 1 201204807 (C1-C60)烷氧基、（C1-C60)烷基硫基、（C6-C60)芳基氧 基、（C6-C60)芳基硫基、單-或二_(cl_C6〇)烷基胺基、 單-或二-(C6-C60)芳基胺基、（C6-C30)芳基（C1-C30) 烷基胺基、三（C1-C30)烷基矽基、二（ci_c3〇)烷基 (C6-C30)芳基矽基、或三（C6_C3〇)芳基矽基；或者Re 與R7、R9與Ri。、及心與&係經由具有或不具稠合環 之（C3-C60)伸烷基或（C3-C60)伸烯基聯結以形成脂肪 環、或單環或多環之芳香環； Y表示（C6-C60)伸芳基、伸金剛烷基、含有一或個 多個雜原子之（C3-C60)雜伸芳基（該雜原子選自n、〇、 s、p、Si 與 Se)、心❽或 Υι表示含有一個或多個雜原子之（C2-60)雜伸芳基 (該雜原子選自^|、0、5、？、5丨與86); Zi與Z2係獨立地表示化學鍵、_(CRl3Ri4)n_、_N(Ri5)一、 、si(Ri6)(R17)---〇-、-S-、-Se-或-(R18)c=C(R19)-，限 制條件為Zi與Z2非同時為化學鍵； Ri3至R19獨立地表示氫、（C1-C60)烷基、（C3-C60) 環烷基、（C6-C60)芳基、含有一個或多個雜原子之 (C2-C60)雜芳基（該雜原子選自N、〇、s、Si與Se)、 (C1-C60)烷氧基、（C1-C60)烷基硫基、（C6-C60)芳基氧 基、（C6-C60)芳基硫基、單-或二-(C1-C60)烷基胺基、 單〜或二-(C6-C60)芳基胺基、（C6-C30)芳基（C1-C30) 燒基胺基、三（C1-C30)烷基矽基、二（C1-C30)烷基 2 95143 201204807 (C6-C30)芳基矽基、或三（C6_C3〇)芳基矽基；或Ri3與 Rh、Rie與Rn ’以及R1S與Rig係經由具有或不具稠合環 之（C3-C60)伸烷基或（C3-C60)伸烯基聯結以形成脂肪 環、或單環或多環之芳香環； a、b與c獨立地表示1至4之整數； d表示1至3之整數；以及 m與η獨立地表示1至4之整數。 .如申請專利範圍第1項所述之有機電場發光化合物，該Wherein Ri to Rs independently represent hydrogen, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl, (C2-C60)heteroaryl containing one or more heteroatoms (The hetero atom is selected from N, 〇, s, p, Si and se), (C1-C60) alkoxy, (C1-C60)alkylthio, (C6-C60) aryloxy, (C6 -C60) arylthio, (C6-C30) aryl (C1_C30) alkylamino, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30) arylhydrazine Base, or tris(C6-C30)aryl fluorenyl X represents chemical KCM7L8), _Si(R9)(Rl.)-, _s-, _Se-, or -(Rn)C=C(R12)~ ; r6 to r12 independently represent hydrogen, (8), pyridyl, (c3_c6〇) cycloalkyl, (10)-(10) aryl, (C2-C6G) heteroaryl containing one or more heteroatoms (the heteroatoms selected From N, 〇, s, Si and Se), 95143 1 201204807 (C1-C60) alkoxy, (C1-C60)alkylthio, (C6-C60) aryloxy, (C6-C60) aryl a thiol group, a mono- or di-(cl_C6 fluorene)alkylamino group, a mono- or di-(C6-C60) arylamino group, a (C6-C30) aryl (C1-C30) alkylamino group, Tris(C1-C30)alkylindenyl, di(ci_c3〇)alkane (C6-C30) aryl group of silicon-based, or tri (C6_C3〇) aryl silicon based; or Re and R7, R9 and Ri. And the heart and & are linked via a (C3-C60)alkylene group or (C3-C60)alkylene group with or without a fused ring to form an aliphatic ring, or a monocyclic or polycyclic aromatic ring; Y represents (C6-C60) an aryl group, an adamantyl group, a (C3-C60) heteroaryl group containing one or more heteroatoms (the hetero atom is selected from the group consisting of n, 〇, s, p, Si, and Se) , ❽ or Υι denotes a (C2-60) heteroaryl group containing one or more heteroatoms (the hetero atom is selected from ^|, 0, 5, ?, 5丨 and 86); Zi and Z2 are independently Represents a chemical bond, _(CRl3Ri4)n_, _N(Ri5)-, s(Ri6)(R17)---〇-, -S-, -Se- or -(R18)c=C(R19)-, limiting The conditions are that Zi and Z2 are not simultaneously chemical bonds; Ri3 to R19 independently represent hydrogen, (C1-C60) alkyl, (C3-C60) cycloalkyl, (C6-C60) aryl, containing one or more heteroatoms (C2-C60)heteroaryl (this hetero atom is selected from N, 〇, s, Si and Se), (C1-C60) alkoxy, (C1-C60)alkylthio, (C6-C60) Aryloxy, (C6-C60) arylthio, mono- or di-(C1-C60)alkylamino, mono- or di-(C6-C60)arylamino, (C6-C30) Aryl (C1-C30) Amino, tri(C1-C30)alkylindenyl, di(C1-C30)alkyl 2 95143 201204807 (C6-C30) aryl fluorenyl, or tris(C6_C3 fluorene) aryl fluorenyl; or Ri3 and Rh, Rie and Rn ' and R1S and Rig are linked via (C3-C60)alkyl or (C3-C60)exetylene with or without a fused ring to form an aliphatic ring, or a monocyclic or polycyclic aromatic a; b, c independently represent an integer from 1 to 4; d represents an integer from 1 to 3; and m and η independently represent an integer from 1 to 4. An organic electroluminescent compound according to claim 1, wherein (R3) 或 (r^係選自下列結構(R3) or (r^ is selected from the following structures 項中任一項所述之有機電場發光化合物。 95143 3 201204807 4·如申請專利範圍第3所述項之有機電場發光敦置，其包 含第一電極；第二電極；以及至少一層置於該第一電極 與該第二電極之間之有機層，其中該有機層包含一種或 多種該有機電場發光化合物，以及一種或多種選自由化 學式3或化學式4表示之化合物之主體： [化學式3] (An)e-Li-(Ar〇f [化學式4] (Ar3)g-L2-(Ar4)h 其中 Li表示（C6-C60)伸芳基或（C4-C60)雜伸芳基； L2表示伸蒽基； An至Ar4獨立地選自氫、氘、（C1-C60)烷基、 (C1-C60)烷氧基、函素、（C4-C60)雜芳基、（C5-C60) 環烧基，以及（C6-C60)芳基，且An至An之該環烧基、 芳基或雜芳基可進一步經一個或多個選自下列所組成 群組之取代基取代·具有或不具一個或多個選自經或未 經鹵素取代之（C1-C60)烷基、（C1-C60)烷氧基、（C3-C60) 環烷基、齒素、氰基、三（C1-C60)烷基矽基、二（C1-C60) 院基（C6-C60)方基石夕基’與三（C6-C60)芳基石夕基之取代 基之（C6-C60)芳基或（C4-C60)雜芳基；經或未經_素取 代之（C1-C60)燒基；（C1-C60)烧氧基；（C3-C60)環烧 基；函素；氰基；三（C1-C60)烷基矽基；二（C卜C6〇) 烷基（C6-C60)芳基矽基；以及三（C6_C6〇)芳基矽基；以 4 95143 201204807 及 e、f、g與h獨立地表示0至4之整數。 5. 如申請專利範圍第4項所述之有機電場發光裝置，其中 該有機層包含一種或多種選自芳基胺化合物與苯乙烯 基芳基胺化合物所組成群組之化合物。 6. 如申請專利範圍第4項所述之有機電場發光裝置，其中 該有機層更包含一種或多種選自第1族、第2族、第4 週期與第5週期之過渡金屬、鑭系金屬與d過渡金屬所 組成群組之金屬。 7. 如申請專利範圍第4項所述之有機電場發光裝置，其為 發出白光之電場發光裝置，其中該有機層更包含一層或 多層發出藍光、紅光或綠光之有機電場發光層。 8. 如申請專利範圍第4項所述之有機電場發光裝置，其中 該有機層包含電場發光層與電荷產生層。 9. 如申請專利範圍第4項所述之有機電場發光裝置，其 中，於該電極對之一個或二個電極之内表面上，係設置 還原性摻雜劑與有機物質之混合區域、或氧化性摻雜劑 與有機物質之混合區域。 5 95143 201204807 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1The organic electroluminescent compound according to any one of the preceding claims. 95143 3 201204807 4. The organic electric field illumination according to claim 3, comprising: a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode Wherein the organic layer comprises one or more of the organic electroluminescent compound, and one or more selected from the group consisting of the compound represented by Chemical Formula 3 or Chemical Formula 4: [Chemical Formula 3] (An)e-Li-(Ar〇f [Chemical Formula 4] (Ar3)g-L2-(Ar4)h wherein Li represents (C6-C60) an aryl group or a (C4-C60) heteroaryl group; L2 represents a fluorenyl group; and An to Ar4 are independently selected from hydrogen, hydrazine , (C1-C60)alkyl, (C1-C60) alkoxy, a functional, (C4-C60)heteroaryl, (C5-C60)cycloalkyl, and (C6-C60)aryl, and An The cycloalkyl, aryl or heteroaryl group to An may be further substituted with one or more substituents selected from the group consisting of: with or without one or more selected from or substituted with halogen ( C1-C60)alkyl, (C1-C60)alkoxy, (C3-C60)cycloalkyl, dentate, cyano, tri(C1-C60)alkyldecyl, di(C1-C60) (C6-C60) a (C6-C60) aryl or (C4-C60)heteroaryl group substituted with a substituent of a sulphate and a tris(C6-C60) aryl fluorenyl group; (C1-C60) substituted with or without _ (C1-C60) alkoxy; (C3-C60) cycloalkyl; cyclin; cyano; tri(C1-C60)alkyl fluorenyl; di(C 卜 C6 〇) alkyl (C6- C60) aryl fluorenyl; and tri(C6_C6 fluorene) aryl fluorenyl; independently representing an integer from 0 to 4 as 4 95143 201204807 and e, f, g and h. 5. as described in claim 4 An organic electric field illuminating device, wherein the organic layer comprises one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds. 6. Organic electric field luminescence as described in claim 4 The device, wherein the organic layer further comprises one or more metals selected from the group consisting of transition metals of Group 1, Group 2, Cycles 4 and 5, and groups of lanthanide metals and d transition metals. The organic electric field illuminating device of claim 4, which is an electric field illuminating device that emits white light, wherein the organic layer further comprises one or more layers of blue light. An organic electric field light-emitting layer according to the invention of claim 4, wherein the organic layer comprises an electric field light-emitting layer and a charge generating layer. The organic electric field light-emitting device according to the invention, wherein a mixed region of a reducing dopant and an organic substance, or an oxidizing dopant and an organic substance is disposed on an inner surface of one or both electrodes of the electrode pair. Mixed area. 5 95143 201204807 IV. Designated representative map: There is no schema in this case (1) The representative representative map 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 化學式2Chemical formula 2 2 95143 201204807 化學式52 95143 201204807 Chemical Formula 5 ❹ (C6CR:Rr立地表示氫、氛、㈣_基、函素、 方基、(C4_⑽)雜芳基、含有一個或多個雜原子 ，其，、凡雜每烧基（該雜原子選自N、0與S)、或（C3-C60) 衣、元土以及該r21與R22之該芳基或雜芳基可進一步經一 個或多個選自下列所組成群組之取代基取代：（C1C60)烧 基齒（Cl C60)烧基、（C1—C60)烧氧基、⑽_C6〇)j^烧基、 (C6 C60)芳基、（C4—⑽）雜芳基、鹵素、氰基、三⑹_C6〇) 烧基石夕基、燒基（C6__芳基妙基，以及三 (C6-C60)芳基;ε夕基； R23至R26獨立地表示氫、氘、（cl_C6〇)烷基、（U_C6〇) 烧氧基、自素、（(：4_⑽）㈣基、（G5_⑽）環絲或⑽-⑽ 21 95143 201204807 第100106624號專利申請H * 100年5月25日修正替換^ 芳基，以及該rZ3至r26之該雜芳基、環烷基或芳基可進— 步經一個或多個選自下列所組成群組之取代基取代：經或 未經i素取代之（Cl-C60)烷基、（C1-C60)烷氧基、（C3-C60) 環烧基、鹵素、氰基、三（C1-C60)烧基石夕基、二（C1-C60) 烷基（C6-C60)芳基矽基，與三（C6-C60)芳基矽基； Lu與Lu獨立地表示化學鍵、或具有或不具一個或多 個選自（C1-C60)烷基、（C1-C60)烷氧基、（C6-C60)芳基、 (C4-C60)雜芳基與鹵素之（C6—C60)伸芳基。 Aru與Arlz獨立地表示選自下列結構之芳基、或表示 卜 (C4-C60)雜芳基；❹ (C6CR: Rr stands for hydrogen, aryl, (d)-yl, cyclin, aryl, (C4_(10))heteroaryl, contains one or more heteroatoms, which are hetero-alkyl groups (the heteroatoms are selected from The N, 0 and S), or (C3-C60) coat, the terbate, and the aryl or heteroaryl group of the r21 and R22 may be further substituted with one or more substituents selected from the group consisting of: ( C1C60) calcined base (Cl C60) alkyl, (C1-C60) alkoxy, (10)_C6〇)j^alkyl, (C6 C60) aryl, (C4—(10))heteroaryl, halogen, cyano, Tris(6)_C6〇) pyridyl group, alkyl group (C6__arylmethylene, and tris(C6-C60) aryl; oxime; R23 to R26 independently represent hydrogen, deuterium, (cl_C6〇) alkyl, (U_C6〇) Alkoxy, self-pyrogenic, ((: 4_(10)))), (G5_(10)), or (10)-(10) 21 95143 201204807 Patent No. 100106624, H*, May 25, 1995, amending aryl, And the heteroaryl, cycloalkyl or aryl group of the rZ3 to r26 may be further substituted with one or more substituents selected from the group consisting of: substituted with or without i (Cl-C60) )alkyl, (C1-C60) alkoxy Base, (C3-C60) cycloalkyl, halogen, cyano, tri(C1-C60) alkyl fluorenyl, di(C1-C60) alkyl (C6-C60) aryl fluorenyl, and tris(C6- C60) aryl fluorenyl; Lu and Lu independently represent a chemical bond, or with or without one or more selected from (C1-C60)alkyl, (C1-C60)alkoxy, (C6-C60)aryl, (C4-C60) Heteroaryl and halogen (C6-C60) extended aryl. Aru and Arlz independently represent an aryl group selected from the following structures, or represents a (C4-C60) heteroaryl group; 其中， 、 ” ΑΓΐ2之5亥芳基或雜芳基可進一步經一個或多個Wherein, ”2 of 5 aryl or heteroaryl may be further passed through one or more 選自（C1⑽）絲、（Π''⑽）院氧基、（C6-C6G)芳基與 (C4-C60)雜芳基之取代基取代； Ll2表示⑽―⑽）伸芳基、（C4-⑽）雜伸芳基、或Substituted from (C1(10)) silk, (Π''(10)) alkoxy, (C6-C6G) aryl and (C4-C60)heteroaryl substituent; Ll2 represents (10)-(10)) aryl, (C4 -(10)) heteroaryl, or 步經一個或多個選自（C1〜 (C6-C60)芳基、（C4_C6〇) 之該伸芳基或雜伸芳基可更進一 C60)烷基、（C1—C6〇)烷氧基、 雜芳基與函素之取代基取代； 95143修正頁 22 第100106624號專利申請案 100年5月25日修正替換頁 201204807 並使用旋轉蒸發器移除溶劑。使用乙醇進行再結晶，得純 化合物 D(64g，73%)。 化合物E之製備 將化合物 D(40g，0. 16mol)、碘（16.9g，0.066mol)、 碘酸（6. 89g，0. 039mol)，加至二頸燒瓶中。加入蒸餾水（30 ml)、醋酸（600ml)與硫酸（14. 4ml)後，混合物於85°C攪拌 4小時。反應完成後，混合物完全冷卻至室溫，並以醋酸 與蒸餾水清洗。經過濾得純化合物E(49g，82%)。 〇 化合物F之製備 將化合物 E(49g，0.13mol)、KOH(33g，0.60mol)與 KI(2.2g, 0.013mol)加至單頸燒瓶中，並於真空下建立氬 氣環境。加入DMS0(無水）（500ml)後，混合物於0°C攪拌 10分鐘。滴加入溴化乙烷（23ml，0. 30mol)，混合物於-10°C 攪拌30分鐘，之後於室溫下攪拌9小時。待反應完成後， 加入過量蒸餾水產生固體，將固體過濾出，所得固體經二 〇 氯甲烷（MC)萃取。有機層以MgS〇4乾燥，並使用旋轉蒸發 器移除溶劑。經管柱層析法，使用己烷作為沖提液，分離 出純化合物F(37g，66%)。 化合物G之製備 將化合物 F(30g，0. 07mol)、咔唑（15. 2g，0. 09mol)、 銅（3.3g，0.05mol)、18-冠醚-6(1.4g，0.005mol)，與 K2C〇3(38.8g, 0.28mol)加至二頸燒瓶中，於真空下建立氬 氣環境。加入1，2-二氯苯（250ml) ’混合物於180°C回流攪 拌6小時。待反應完成後，使用矽藻土過濾器移除銅，反 31 95143修正頁 201204807 應混合物溶於MC中。移除溶劑後，經管柱層析法，使用二 氯曱烧與己烷作為沖提液，分離出純化合物G(23g，76%)。 化合物Η之製備 將化合物G(20g，〇. 〇42mol)加至單頸燒瓶中，建立氮 氣環境。加入THF後，混合物於-78°C攪拌10分鐘。滴加 入正-丁基鐘（2. 5M於己烷中）（40ml，〇.〇63mol)，混合物 於-78 C 攪拌 1 小時。之後，加入 dmf(4. 8ml，0. 063mmol)， 混合物攪拌10分鐘’之後於室溫下攪拌4小時。待反應完 成後’加入HC1(2. 5ml)，冷卻至室溫。使用蒸餾水與EA 萃取。有機層以MgS〇4乾燥’並使用旋轉蒸發器移除溶劑。 經管柱層析法’使用己烷與EA作為沖提液，分離出純化合 物 H(13g， 72%)。 化合物I之製備 將化合物H(13g，〇. 〇31mol)與三乙基亞膦酸酯（l〇mi， 0. 062mol)加至單頸燒瓶中。於〇。〇加入碘（7. 9g，0. 〇31 mol)後’混合物攪拌30分鐘，之後於室溫攪拌12小時。 待反應完成後，使用真空昇華器移除亞膦酸酯，並使用蒸 顧水與EA進行萃取。有機層以MgS〇4乾燥，並使用旋轉蒸 發器移除溶劑。經管柱層析法，使用己烷與EA作為沖提 液，分離出純化合物I(16g，87%)。 化合物91之製備 將化合物 I(16g，0. 029mol)與化合物 C(7.6g，0.029 mo 1)加至單頸燒瓶中，於真空下建立氬氣環境。加入THF (600ml)後，混合物於0°C攪拌1〇分鐘，緩慢加入第三丁 32 95143The one or more of the aryl or heteroaryl groups selected from (C1~(C6-C60) aryl, (C4_C6〇) may further be a C60) alkyl group, a (C1-C6〇) alkoxy group. Substituent substitution of a heteroaryl group and a hydroxyl group; 95143 Amendment Page 22 Patent Application No. 100106624, May 25, 100, revised replacement page 201204807 and using a rotary evaporator to remove the solvent. Recrystallization from ethanol gave pure compound D (64 g, 73%). Preparation of Compound E Compound D (40 g, 0.16 mol), iodine (16.9 g, 0.066 mol), iodic acid (6.99 g, 0.039 mol) was added to a two-necked flask. After adding distilled water (30 ml), acetic acid (600 ml) and sulfuric acid (14.4 ml), the mixture was stirred at 85 ° C for 4 hours. After the reaction was completed, the mixture was completely cooled to room temperature and washed with acetic acid and distilled water. Pure compound E (49 g, 82%) was obtained by filtration.之 Preparation of Compound F Compound E (49 g, 0.13 mol), KOH (33 g, 0.60 mol) and KI (2.2 g, 0.013 mol) were placed in a one-necked flask and an argon atmosphere was established under vacuum. After adding DMS0 (anhydrous) (500 ml), the mixture was stirred at 0 ° C for 10 min. Ethyl bromide (23 ml, 0.30 mol) was added dropwise, and the mixture was stirred at -10 ° C for 30 min, then stirred at room temperature for 9 hr. After the reaction was completed, excess distilled water was added to give a solid, the solid was filtered, and the obtained solid was extracted with dichloromethane. The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. Pure compound F (37 g, 66%) was isolated by column chromatography using hexane as a solvent. Preparation of Compound G, Compound F (30 g, 0.07 mol), carbazole (1. 2 g, 0.09 mol), copper (3.3 g, 0.05 mol), 18-crown-6 (1.4 g, 0.005 mol), K2C 3 (38.8 g, 0.28 mol) was added to a two-necked flask to establish an argon atmosphere under vacuum. A mixture of 1,2-dichlorobenzene (250 ml) was added and the mixture was refluxed at 180 ° C for 6 hours. After the reaction is completed, remove the copper using a diatomaceous earth filter. Reverse 31 95143 Amendment Page 201204807 The mixture should be dissolved in MC. After removing the solvent, pure compound G (23 g, 76%) was isolated by column chromatography using chlorobenzene and hexane as a solvent. Preparation of the compound hydrazine Compound G (20 g, 〇. 〇 42 mol) was added to a one-necked flask to establish a nitrogen atmosphere. After the addition of THF, the mixture was stirred at -78 ° C for 10 min. It was added dropwise to a n-butyl oxime (2.5 M in hexane) (40 ml, EtOAc, EtOAc), and the mixture was stirred at -78 C for one hour. Thereafter, dmf (4.8 ml, 0.063 mmol) was added, and the mixture was stirred for 10 minutes' and then stirred at room temperature for 4 hours. After the reaction was completed, HCl (2.5 ml) was added and cooled to room temperature. Extract with distilled water and EA. The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. The purified compound H (13 g, 72%) was isolated by column chromatography using hexane and EA as solvent. Preparation of Compound I Compound H (13 g, 〇. 〇 31 mol) and triethylphosphonite (1 〇 mi, 0. 062 mol) were added to a one-necked flask. Yu Yu. After adding iodine (7.9 g, 0.13 mol), the mixture was stirred for 30 minutes and then stirred at room temperature for 12 hours. After the reaction was completed, the phosphinate was removed using a vacuum sublimator and extracted with steamed water and EA. The organic layer was dried with MgS 4 and the solvent was removed using a rotary evaporator. By column chromatography, pure compound I (16 g, 87%) was isolated using hexane and EA as a solvent. Preparation of Compound 91 Compound I (16 g, 029 mol) and Compound C (7.6 g, 0.029 mol) were placed in a one-necked flask to establish an argon atmosphere under vacuum. After adding THF (600 ml), the mixture was stirred at 0 ° C for 1 Torr, and slowly added to the third butyl 32 95143
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