TW201204809A - 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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TW201204809A
TW201204809A TW100114601A TW100114601A TW201204809A TW 201204809 A TW201204809 A TW 201204809A TW 100114601 A TW100114601 A TW 100114601A TW 100114601 A TW100114601 A TW 100114601A TW 201204809 A TW201204809 A TW 201204809A
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Taiwan
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group
aryl
alkyl
heteroaryl
cycloalkyl
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TW100114601A
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Chinese (zh)
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Hyo-Jung Lee
Young-Jun Cho
Hyuck-Joo Kwon
Bong-Ok Kim
Sung-Min Kim
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Rohm & Haas Elect Mat
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Publication of TW201204809A publication Critical patent/TW201204809A/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
    • C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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Abstract

Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound exhibits good luminous efficiency in blue color and excellent life property of the material, it may be used to manufacture OLED devices having very superior operation life.

Description

201204809 . 六、發明說明： 【發明所屬之技術領域】 • 本發明係關於新穎有機電場發光化合物及使用該化合 . 物之有機電場發光裝置，更具體而言，本發明係關於作為 - 藍色電場發光材料使用之新穎有機電場發光化合物及使用 該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，電場發光（electroluminescent, EL) 裝置作為自體發射顯示器裝置具有下列優點：其提供寬廣 之視角、較高之對比度及快速的反應速率。於1987年，伊 斯門''柯達（Eastman Kodak)率先研發出一種有機EL裝置， 其係使用低分子量芳香族二胺及鋁之錯合物作為形成電場 發光層之物質[jpp人比51，913，1987]。 於有機EL裝置中’決定其包含發光效率及操作壽命之 效能的最重要因素係電場發光材料。對於該電場發光材料 的某些要求包含在固態之高電場發光量子產率、高電子及 電洞遷移性、於真空沈積過程對分解之抗性、以及形成均 勻薄膜之能力及安定性。 有機電場發光材料一般可分為高分子材料及低分子材 料。就分子結構層面來看，該低分子材料包含金屬錯合物 及不含金屬之完全有機電場發光材料。此等電場發光材料 包含螯合劑錯合物諸如參（8-羥基喹啉基）鋁錯合物〇^5 (8-qUin〇linolato)aiuminum c〇mplex)、香豆素衍生物、 四苯基丁二烯衍生物、雙（苯乙婦基伸芳基）衍生物及曙二 95221 3 201204809 唑衍生物。已有報導指出可由彼等材料獲得從藍色至紅色 的可見光區域之發光，且該等材料預期可實現全彩顯示器 裝置。 同時，對於傳統的藍色材料而言，自日本出光興產株 式會社（Idemitsu-Kosan)研發二苯基乙烯基_聯苯（DpvBi) (化合物a)以來，許多材料已被研發及商品化。除了 Idemitsu-Kosan的藍色材料系統外，亦已知柯達（K〇dac) 的二萘基蒽（DNA)(化合物b)、肆（第三丁基）茈（化合物c) 糸統專。然而，關於這些材料仍應進行多方面的研究及研 發0 目刖以最南效率聞名的Idemitsu-Kosan之桂皮基 (distryl)化合物系統具有6流明/瓦（lm/w)的功率效率以 及超過30, 000小時的有用裝置壽命。然:而，當將該系統應 用於全彩顯不器時，由於在操作時間期間之色 降’壽命僅為幾千小時。在藍色電場發光 又 場發光波長往較長波長方㈣許移動，從右電 更為有利。然而，因為藍色色純度不足，^ ^之觀點 應用於高品質之顯示器。此外，由於色纯片不易將該材料 定性等問題，因此亟需研究及開發該等材^、效率及熱安 95221 4 201204809201204809. 6. Description of the Invention: [Technical Field of the Invention] The present invention relates to a novel organic electroluminescent compound and an organic electric field illuminating device using the same, and more particularly, the present invention relates to a blue electric field A novel organic electroluminescent compound for use in a luminescent material and an organic electric field illuminating device using the compound as a dopant. [Prior Art] In a display device, an electroluminescent (EL) device as a self-emissive display device has the advantages of providing a wide viewing angle, a high contrast ratio, and a fast reaction rate. In 1987, Eastman Kodak pioneered the development of an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a substance for forming an electroluminescent layer [jpp ratio 51, 913, 1987]. The most important factor in determining the efficacy of luminescent efficiency and operational lifetime in an organic EL device is an electroluminescent material. Some of the requirements for the electroluminescent material include high field luminescence quantum yield in the solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, and the ability to form a uniform film and stability. Organic electroluminescent materials are generally classified into polymer materials and low molecular materials. In terms of molecular structure, the low molecular material comprises a metal complex and a metal-free fully organic electroluminescent material. These electroluminescent materials comprise a chelating agent complex such as quinone (8-hydroxyquinolinyl)aluminum complex 8^5 (8-qUin〇linolato)aiuminum c〇mplex), coumarin derivative, tetraphenyl Butadiene derivatives, bis(phenethyl aryl) derivatives and oxime II 95221 3 201204809 azole derivatives. It has been reported that illuminating from the blue to red visible regions can be obtained from their materials, and that such materials are expected to achieve full color display devices. At the same time, many materials have been developed and commercialized since the development of diphenylvinyl-biphenyl (DpvBi) (Compound a) by Idemitsu-Kosan, a traditional blue material. In addition to the blue material system of Idemitsu-Kosan, dinaphthyl quinone (DNA) (compound b) and hydrazine (t-butyl) hydrazine (compound c) of K〇dac are also known. However, there is still a wide range of research and development on these materials. 0 The Idemitsu-Kosan distryl compound system, known for its most southern efficiency, has a power efficiency of 6 lumens per watt (lm/w) and over 30. , 000 hours of useful device life. However, when the system is applied to a full color display, the color loss during the operating time is only a few thousand hours. In the blue electric field, the field emission wavelength is shifted to the longer wavelength side (four), and it is more advantageous from the right. However, because the purity of the blue color is insufficient, the viewpoint of ^ ^ is applied to a high-quality display. In addition, since it is difficult to characterize the material, it is urgent to research and develop the materials, efficiency and heat. 95221 4 201204809

【發明内容】 技術問題 為了克服上述傳統技術的問題而密集努 者發明-簡财機電場發光化合物， 案發明 tt 光效率及顯著改善操作壽命性質的有機電場】=異發 發明之目的係提供—種有機電場發光化合、本 具有帶適當的色座標之骨架以提供與雜2化合物 更好的發光效率及裝置壽命，同時克 紹吏用該有機電場發光化合物之高效率且2二it 場發光裝置。 焚可命的有機， 技術解決方案 人仏考x月提么、種新穎有機電場發光化合物及使用該化 之有機電發光裝置。該有機電場發光化合物為化學 斤丁之化合物。由於本發明之有機電場發光化合物具 交同的發光效率及優異的壽命性f，因此其可用於製造 具有極高操作壽命之0LED裝置。 化學式1 5 95221 201204809SUMMARY OF THE INVENTION Technical Problem In order to overcome the problems of the above-mentioned conventional techniques, an intensive invention has been invented - an electric field illuminating compound, and an organic electric field which significantly improves the life of the operating life. An organic electric field illuminating compound, having a skeleton with an appropriate color coordinate to provide better luminous efficiency and device lifetime with the hybrid compound, and a high efficiency and 2 nd field illuminating device using the organic electroluminescent compound . Increasingly combustible organic, technical solutions. A new type of organic electroluminescent compound and an organic electroluminescent device using the same. The organic electroluminescent compound is a chemical compound. Since the organic electroluminescent compound of the present invention has the same luminous efficiency and excellent lifetime f, it can be used to manufacture an OLED device having an extremely high operational life. Chemical formula 1 5 95221 201204809

二？: ？广蜀立表示氫、(㈣^ %院基、…員雜環统基、(C6， 芳基、-_[其中HRf係獨立 ^ ⑽谓芳基]、RWSi-[其中^㈣獨立表; (C卜C30)烧基或（C6-C30)芳基]、RV[其中，γ表禾〇或s 且R表示（C1-C30)烧基或（C6-C30)芳基]咬 R*I2 但排除Ri、R4、R7及R1d中之兩者為氫之情況； r2、r3、r5、r6、匕及r9係獨立表示氫、（c卜c3〇)烷基、 (C3-C3G)職基、5至7 S雜環絲、⑽_G3G)芳基、 (C2-C30)雜芳基、_Nim其中，Rm系獨立表示（C1_C30) 烷基或（C6-C30)芳基]、RaRbRcSi-[其中，R、Rb& RC係獨立 表示（C1-C30)烷基或（C6-C30)芳基]或RdY_[其中，γ表示〇 或S，且Rd表示（C1-C30)烷基或（C6-C30)芳基]; L·表示單鍵、（C6-C30)伸芳基或（C2-C30)伸雜芳基； L2表示（C6-C30)伸芳基、（C2-C30)伸雜芳基或two? : ?广蜀立 stands for hydrogen, ((4)^% of the base, ... heterocyclic ring, (C6, aryl, -_[where HRf is independent ^ (10) is aryl], RWSi-[where ^ (four) independent table; C (C30) alkyl or (C6-C30) aryl], RV [wherein γ or s and R represents (C1-C30) alkyl or (C6-C30) aryl] biting R*I2 but Excluding the case where two of Ri, R4, R7 and R1d are hydrogen; r2, r3, r5, r6, 匕 and r9 independently represent hydrogen, (ccc3〇)alkyl, (C3-C3G), 5 to 7 S heterocyclic, (10)-G3G) aryl, (C2-C30)heteroaryl, _Nim wherein Rm independently represents (C1_C30) alkyl or (C6-C30) aryl], RaRbRcSi-[where R Rb&RC is independently represented by (C1-C30)alkyl or (C6-C30)aryl] or RdY_[wherein γ represents 〇 or S, and Rd represents (C1-C30)alkyl or (C6-C30) Aryl]; L· represents a single bond, (C6-C30) extended aryl or (C2-C30) extended heteroaryl; L2 represents (C6-C30) extended aryl, (C2-C30) heteroaryl or

心及Rlz係獨立表示（C3-C30)環烷基、5至7員雜環院 6 95221 201204809Heart and Rlz are independent representations of (C3-C30) cycloalkyl, 5 to 7 member heterocyclic hospitals. 6 95221 201204809

基、（C6-C30)芳基、（C2-C30)雜芳基或•，或者Base, (C6-C30) aryl, (C2-C30)heteroaryl or •, or

Ru及R。可經由具有或不具有稠合環之（C3_C3〇)伸烷基或 (C3-C30)伸烯基相鏈結以形成稠合環，且該伸烷基的碳原 子可經NR21、0、或S取代，其中r21表示氫、（C1-C30)烷 基、鹵（C1-C30)烷基、（C1_C3〇)烷氧基、N_嗎啉基 (morpholino)、N_硫代嗎啉基(thi〇m〇rph〇lin〇)、N -哌啶 基、5至7員雜環烷基、（C3_C3〇)環烷基、函素、氰基、 (C6-C30)芳基、（C2-C30)雜芳基或 RaRbRcsi-[其中，Ra、Rb 及R係獨立表示（C1-C30)烷基或（C6-C30)芳基]; Z!及 Z2 係獨立表示 _(；CR3iR32\_、_(R3i)c=c(R32)_、 -N(R33)-、-s-、-〇—、_Se_或_Si(R34)(R35); 心至R35係獨立表示氫、（C1-C30)烷基、（C3-C30)環烷 基、^至7員雜環烷基、（C6-C30)芳基、（C2-C30)雜芳基、 NR R [其中，Ri Rf係獨立表示（cl_C3〇)烷基或（C6_c3〇) 芳基]、或mw-[其中，“ RC係獨立表示（cl_C3〇) 烧基或（C6-C3〇)芳基];或者R3i至R35可各自經由具有或不 具有稠合環之伸絲或（G3_⑽）伸縣鏈結至相 鄰取代基以形成脂環族環、或單環或多環之芳香環；Ru and R. The fused ring may be formed via a (C3_C3〇)alkyl or (C3-C30) extended alkenyl phase chain with or without a fused ring, and the carbon atom of the alkyl group may be NR21, 0, or Substituting S, wherein r21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1_C3〇)alkoxy, N-morpholino, N-thiomorpholinyl ( Thi〇m〇rph〇lin〇), N-piperidinyl, 5- to 7-membered heterocycloalkyl, (C3_C3〇)cycloalkyl, cyclin, cyano, (C6-C30) aryl, (C2- C30) Heteroaryl or RaRbRcsi- [wherein, Ra, Rb and R are independently represented by (C1-C30) alkyl or (C6-C30) aryl]; Z! and Z2 are independently represented by _(; CR3iR32\_, _(R3i)c=c(R32)_, -N(R33)-, -s-, -〇-, _Se_ or _Si(R34)(R35); Heart to R35 are independent of hydrogen, (C1- C30) alkyl, (C3-C30)cycloalkyl, ^ to 7-membered heterocycloalkyl, (C6-C30) aryl, (C2-C30)heteroaryl, NR R [wherein Ri Rf is independently represented (cl_C3〇)alkyl or (C6_c3〇)aryl], or mw-[wherein, "RC is independently represented by (cl_C3〇)alkyl or (C6-C3〇)aryl]; or R3i to R35 are each via With or without a fused ring Filaments or (G3_⑽) extending adjacent to County link substituent group to form an alicyclic ring, or the monocyclic or polycyclic aromatic ring;

Ri至Rn及r31至r35之該燒基、環烧基、雜環烧基、芳 j雜芳基；Ll及L2之該伸芳基或伸雜芳基；Rn及R12之 2燒基、雜環縣、芳基或雜芳基；以及經由將R11及R12 鏈：所形成之該稠合環’係可進一步經一個或多個選自 抓Cl C30)燒基、（C6_C30)芳基、（c卜_烧氧基、氛 95221 7 201204809 基、（C1-C30)烷基矽烷基、（C6-C30)芳基矽烷基、鹵（C1-C30) 院基、（C3-C30)雜芳基、（C3_C3〇)環烷基、硝基及羥基之 取代基所取代； 該雜環烷基或雜芳基可含有一個或多個選自b、n、o、 S ' P(=0)、Si及P之雜原子；以及 m表示整數0、1或2。 【實施方式】 在本發明中，「（C1-C30)烷基、三（C1-C30)烷基矽烷 基、二（C1-C30)烷基（C6-C30)芳基矽烷基、（C6-C30)芳基 (C1-C30)烷基、（C1-C30)烷氧基、（C1-C30)烷硫基」等的 烷基部份可具有1至20個碳原子，更具體而言，可具有1 至 10 個碳原子。「（C6-C30)芳基、二（n-C30)烷基（C6-C30) 芳基矽烷基、三（C6-C30)芳基矽烷基、（C6-C30)芳基 (C1-C30)烷基、（C6-C30)芳氧基、（C6-C30)芳硫基」等的 芳基部份可具有6至20個碳原子，更具體而言，可具有6 至12個碳原子。「（C3-C30)雜芳基」的雜芳基部份可具有 4至20個碳原子，更具體而言，可具有4至12個碳原子。 「（C3-C30)環氧基」的環氧基部份可具有3至2〇個碳原 子，更具體而言，可具有3至7個碳原子。「（C2-C30)烯基 或炔基」的稀基或炔基部份可具有2至20個碳原子，更具 體而言，可具有2至1〇個碳原子。 在本發明中，「烷基」係包含只含有碳原子及氫原子之 直鏈或分支鍵之飽和單價烴基，或其組合物。在本發明中， 「環烷基」係包含多環烴環諸如金剛烷基或雙環烷基，以 95221 201204809 „ 及單環。 在本發明中，「芳基」係意指自芳香烴去除一個氫原子 後所得之有機基團，且可包含4至7員（特別是指5員或6 • 員）之單環或稠合環，包含複數個含有於其間之單鍵之芳 ； 基。具體實例包括：苯基、萘基、聯苯基、蒽基、茚基、 苐基、菲基、聯伸三苯基（tripenylenyl)、芘基、茈基、 蒯基（chrysenyl)、稍四苯基（naphthacenyl)、丙二烯合第 基（fluoranthenyl)等，但並不限於此。該萘基包括1-萘 基及2-萘基。該蒽基包括卜蒽基、2-蒽基及9-蒽基，且 該第基包括1-第基、2-第基、3-第基、4-苐基以及9-第基。 在本發明中，「雜芳基」係意指含有作爲芳香環骨架原子之 選自B、N、0、S、P(=0)、Si及P之1至4個雜原子，以 及作為其它剩餘芳香環骨架原子之碳原子之芳基。該雜芳 基可為5員或6員單環雜芳基或為與苯環縮合所得之多環 雜芳基，且可呈部分飽和。該雜芳基也包含具有於其間之 單鍵之雜芳基。 該雜芳基包括二價芳基’其中，該環中的雜原子可經 氧化或四級化以形成，諸如：N-氧化物或四級鹽。具體實 例包括：單環雜芳基，諸如呋喃基、噻吩基、吡咯基、咪 唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異噚唑基、 噚唑基、卩等二唑基、三畊基、四ti井基、三唑基、四唑基、 呋咕基（furazanyl)、吡啶基、吡卩井基、嘧啶基、嗒畊基等； 多環雜芳基，諸如苯并呋喃基、笨并噻吩基、異苯并呋喃 基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異口等 9 95221 201204809 峻基、笨并噚唑基、異吲哚基、吲哚基、吲唑基、苯并噻 二唑基、喹啉基、異喹啉基、噌啉基、喹唑啉基、喹噚啉 基、味α坐基、啡咬基及苯并二曙呃基（benz〇di〇x〇lyl)等， 其N-氧化物（諸如：D比咬基N-氧化物及嗤琳基N-氧化物） 其四級鹽；等’但並不限於此。 此外，本發明之有機電場發光化合物係包含下列化學 式2或3所示之化合物： 化學式2Ri to Rn and r31 to r35 of the alkyl group, cycloalkyl group, heterocyclic alkyl group, aryl j heteroaryl group; L1 and L2 of the aryl or heteroaryl group; Rn and R12 of 2 alkyl, hetero Ring, aryl or heteroaryl; and via the R11 and R12 chains: the fused ring' formed may be further passed through one or more selected from the group consisting of CCl(30), (C6_C30) aryl, c Bu-Oxygen, atmosphere 95221 7 201204809 base, (C1-C30) alkyl decyl, (C6-C30) aryl decyl, halogen (C1-C30), (C3-C30) heteroaryl Substituting (C3_C3〇) a substituent of a cycloalkyl group, a nitro group and a hydroxyl group; the heterocycloalkyl group or heteroaryl group may contain one or more selected from the group consisting of b, n, o, S ' P (=0), a hetero atom of Si and P; and m represents an integer of 0, 1, or 2. In the present invention, "(C1-C30)alkyl, tri(C1-C30)alkyldecane, di(C1- C30) an alkyl (C6-C30) aryl decyl group, (C6-C30) aryl (C1-C30) alkyl group, (C1-C30) alkoxy group, (C1-C30) alkylthio group, etc. The base moiety may have from 1 to 20 carbon atoms, and more specifically, may have from 1 to 10 carbon atoms. "(C6-C30) aryl, two (n-C30)alkyl (C6-C30) aryldecyl, tris(C6-C30)aryldecyl, (C6-C30)aryl(C1-C30)alkyl, (C6-C30) aryloxy The aryl moiety of the group, (C6-C30) arylthio" or the like may have 6 to 20 carbon atoms, and more specifically, may have 6 to 12 carbon atoms. "(C3-C30) Heteroaryl" The heteroaryl moiety may have 4 to 20 carbon atoms, and more specifically, may have 4 to 12 carbon atoms. The epoxy moiety of "(C3-C30) epoxy group may have 3 to 2 One carbon atom, more specifically, may have from 3 to 7 carbon atoms. The dilute or alkynyl moiety of "(C2-C30)alkenyl or alkynyl" may have from 2 to 20 carbon atoms, more specifically In the present invention, the "alkyl group" is a saturated monovalent hydrocarbon group containing a linear or branched bond containing only a carbon atom and a hydrogen atom, or a combination thereof. The "cycloalkyl group" includes a polycyclic hydrocarbon ring such as an adamantyl group or a bicycloalkyl group as 95221 201204809 „ and a monocyclic ring. In the present invention, the term “aryl group” means after removing a hydrogen atom from an aromatic hydrocarbon. The resulting organic group, and A monocyclic or fused ring comprising 4 to 7 members (especially 5 members or 6 members), comprising a plurality of aromatic groups containing a single bond therebetween; specific examples include: phenyl, naphthyl, biphenyl Base, fluorenyl, fluorenyl, fluorenyl, phenanthryl, trienylylene, fluorenyl, fluorenyl, chrysenyl, naphthacenyl, fluoranthenyl ), etc., but not limited to this. The naphthyl group includes 1-naphthyl and 2-naphthyl. The fluorenyl group includes a decyl group, a 2-fluorenyl group and a 9-fluorenyl group, and the group includes a 1-position group, a 2-position group, a 3-position group, a 4-anthrace group and a 9-position group. In the present invention, "heteroaryl" means one to four hetero atoms selected from B, N, 0, S, P (=0), Si and P as an aromatic ring skeleton atom, and as other The aryl group of the carbon atom of the remaining aromatic ring skeleton atom. The heteroaryl group may be a 5- or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group obtained by condensation with a benzene ring, and may be partially saturated. The heteroaryl group also contains a heteroaryl group having a single bond therebetween. The heteroaryl group includes a divalent aryl group wherein the hetero atom in the ring may be oxidized or quaternized to form, such as an N-oxide or a quaternary salt. Specific examples include: a monocyclic heteroaryl group such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, anthracene, etc. Diazolyl, tri-nurgical, tetra-ti, triazolyl, tetrazolyl, furazanyl, pyridyl, pyridinium, pyrimidinyl, hydrazine, etc.; polycyclic heteroaryl, Such as benzofuranyl, benzothiophene, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzo isomer, etc. 9 95221 201204809 Junji, stupid and carbazolyl, Isoindolyl, fluorenyl, carbazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, porphyrinyl, quinazolinyl, quinoxalinyl, s-alpha, morphine And benzodiazepine (benz〇di〇x〇lyl), etc., its N-oxide (such as: D than bite-based N-oxide and sulfinyl N-oxide) its quaternary salt; 'But it is not limited to this. Further, the organic electroluminescent compound of the present invention contains a compound represented by the following Chemical Formula 2 or 3: Chemical Formula 2

化學式3Chemical formula 3

n4 R5R6 HrN4 R5R6 Hr

其中，among them,

Ln及U係獨立表示（C6-C30)伸芳基、（C2-C30)伸雜芳Ln and U are independent representations (C6-C30) aryl, (C2-C30)

基或 ； L21及L”係獨立表示（C6-C30)伸芳基或（C2-C30)伸雜 芳基； 10 95221 201204809 R2、R3、R5、R6、匕及匕係獨立表示氫、（n-C30)烷基、 (C3-C30)環烷基、5至7員雜環烷基、（C6-C30)芳基或（C2-C30)雜芳基； 尺“至R44係獨立表示（C3-C30)環烷基、5至7員雜環烷L21 and L" independently represent (C6-C30) aryl or (C2-C30) heteroaryl; 10 95221 201204809 R2, R3, R5, R6, fluorene and fluorene independently represent hydrogen, (n -C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-C30)aryl or (C2-C30)heteroaryl; scale "to R44" independent (C3 -C30) cycloalkyl, 5 to 7 membered heterocycloalkane

基、（C6-C30)芳基、（C2-C30)雜芳基或 -*，或者 L至R“可經由具有或不具有稠合環之（C3-C30)伸烷基或 (C3-C30)伸烯基相鏈結以形成稠合環’且該伸烷基的碳原 子可經眺！、0、或S取代，其中R21表示氫、（C1-C30)烷 基、_(C1-C30)烷基、（C卜C30)烷氧基、N-嗎啉基、N-硫 代嗎啉基、N-哌啶基、5至7員雜環烷基、（C3-C30)環烷 基、鹵素、氰基、（C6-C30)芳基、（C2-C30)雜芳基或RaRbResi- [其中，Ra、Rb及Rc係獨立表示（C1-C30)烷基或（C6-C30)芳 基]; Ζι 及 Z2 係獨立表示、-(r31)c=c(r32)_、 -N(R33)-、-S-、-0-、-se-或-Si(R34)(R35); R31至R35係獨立表示氫、（C1-C30)烧基、（C3-C30)環燒 基、5至7員雜環烷基、（C6_C30)芳基、（C2_C3〇)雜芳基、 -NReRf[其中’ Re及係獨立表示（C1_C30)烷基或（C6—c3〇) 芳基]或RaRbReSi-[其中，Ra、Rb及係獨立表示（Cl_C3〇) 烷基或（C6-C30)芳基];或者心至R35可各自經由具有或不 具有稠合環之（C3-C30)伸烷基或（C3-C30)伸烯基鏈結至相 鄰取代基以形成脂環族環、或單環或多環之芳香環； R〗、R4、R7及R1D係獨立表示氫、（C1_C30)烷基、（C3—c別） 95221 11 201204809 環烷基、5至7員雜環烷基、（C6_C3〇)芳基、（C2_C3〇)雜 芳基、_NReRf[其中，γ及Rf係獨立表示卜烷基或 (C6-C30)芳基]、RaRbRcsi-[其中，γ、Rb及RC係獨立表示 (C1-C30)烷基或（C6-C30)芳基]或RdY-[其中，γ表示〇或 S，且Rd表示（C1-C30)烷基或（C6-C30)芳基]；, (C6-C30) aryl, (C2-C30)heteroaryl or -*, or L to R" may be via (C3-C30)alkyl or (C3-C30) with or without a fused ring An alkenyl phase chain to form a fused ring' and the carbon atom of the alkyl group may be substituted with hydrazone, 0, or S, wherein R21 represents hydrogen, (C1-C30) alkyl, _(C1-C30 Alkyl, (C-C30) alkoxy, N-morpholinyl, N-thiomorpholinyl, N-piperidinyl, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl , halogen, cyano, (C6-C30) aryl, (C2-C30)heteroaryl or RaRbResi- [wherein, Ra, Rb and Rc independently represent (C1-C30) alkyl or (C6-C30) aryl ]ι and Z2 are independent representations, -(r31)c=c(r32)_, -N(R33)-, -S-, -0-, -se- or -Si(R34)(R35); R31 to R35 are independently represented by hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6_C30)aryl, (C2_C3〇)heteroaryl, -NReRf [wherein 'Re and independently represent (C1_C30) alkyl or (C6-c3〇) aryl) or RaRbReSi-[wherein, Ra, Rb and independently represent (Cl_C3〇) alkyl or (C6-C30) aryl ]; or heart to R35 can be via each with or without a (C3-C30)alkylene group having a fused ring or a (C3-C30)alkylene chain to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; R, R4 , R7 and R1D are independently represented by hydrogen, (C1_C30)alkyl, (C3-c) 95221 11 201204809 cycloalkyl, 5 to 7 membered heterocycloalkyl, (C6_C3〇) aryl, (C2_C3〇) heteroaryl , _NReRf [wherein γ and Rf independently represent alkyl or (C6-C30) aryl], RaRbRcsi-[wherein γ, Rb and RC are independently represented by (C1-C30) alkyl or (C6-C30) Or an aryl] or RdY-[wherein γ represents 〇 or S, and Rd represents (C1-C30)alkyl or (C6-C30) aryl];

Ri至Ri。之該烷基、環烷基、雜環烷基'芳基或雜芳基； 以及L"、Lk、Lu及L22之該伸芳基或伸雜芳基可進一步經 一個或多個選自氘、（C1-C30)烷基、（C6-30)芳基、（C1-C30) 烷氧基、氰基、（C1-C30)烷基矽烷基、（C6-C30)芳基矽烷 基、齒（C1-C30)烷基、（C3-C30)雜芳基、（C3-C30)環烷基、 硝基及羥基之取代基所取代；以及 m表示整數〇、1或2。 該L"及L12係獨立表示伸苯基、伸萘基、伸聯苯基、 伸菲基、伸°比畊基、伸三畊基、伸喹啉基、伸啡啉基、伸 嘆吩基、伸17夫喃基、伸叾西苯基（selenophenylene)、伸嗟二 °坐基、伸卩等二唾基、伸碰二β坐基（selenadiazolylene)或伸 喹噚啉基，或者為選自下列結構之二價基團：Ri to Ri. The alkyl, cycloalkyl, heterocycloalkyl 'aryl or heteroaryl group; and the aryl or heteroaryl group of L", Lk, Lu and L22 may further be selected from one or more selected from the group consisting of hydrazine (C1-C30)alkyl, (C6-30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkyldecyl, (C6-C30)aryldecyl,dentate Substituted by a substituent of (C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxy; and m represents an integer 〇, 1 or 2. The L" and L12 series independently represent a phenylene group, a naphthyl group, a phenylene group, a phenanthrene group, a stretching ratio, a cultivating base, a stretching quinculin, a quinolinyl group, a phenanthroline group, an exoskele group, Stretching sulphate, selenophenylene, sputum, sputum, sputum, etc., selenadiazolylene or quinoxaline, or selected from the following Structure of the divalent group:

1^至R35係獨立表示氫、甲基、乙基、正丙基、異丙基、 正丁基、異丁基、第三丁基、戊基、戊烷基（amyl)、己基、 庚基、辛基、壬基、癸基、三氟曱基、苯基、萘基、聯苯 12 95221 201204809 基、苐基或菲基，或者1^至R35可各自經由具有或不具有 稠合環之（C3-C30)伸烷基或（C3-C30)伸烯基鏈結至相鄰取 代基以形成脂環族環、或單環或多環之芳香環； L21及L22係獨立表示伸苯基、伸萘基、伸蒽基、伸苐基、 伸菲基、伸聯苯基、伸三苯基（triphenylene)、伸丙二烯 合第基（丨1110『&111±611716116)、伸蒯基、伸芘基、伸茈基、 伸°比°定基、伸吱喃基、伸嘆吩基、伸磁苯基、伸η比哄基、 伸嗒啡基、伸喹啉基或伸喹噚啉基；1^ to R35 independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, amyl, hexyl, heptyl , octyl, decyl, decyl, trifluoromethyl, phenyl, naphthyl, biphenyl 12 95221 201204809, fluorenyl or phenanthryl, or 1^ to R35, each via or without a fused ring (C3-C30) alkyl or (C3-C30) an alkenyl chain to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; L21 and L22 independently represent a phenyl group , anthranyl, anthracenyl, anthracenyl, phenanthrene, phenyl, triphenylene, and adiene (丨1110&111±611716116) , stretching base, stretching base, stretching ratio, fixing base, stretching thiol, stretching thiophene, stretching phenyl, stretching η than sulfhydryl, stretching quinone, quinolinyl or quinoxaline base;

尺2、R3、Rs、Re、Re及R9係獨立表示氳、甲基、乙基、 正丙基、異丙基、正丁基、異丁基、第三丁基、戊基、戊 烧基、己基、庚基、辛基、壬基、癸基、三氟甲基、環丙 基、環丁基、環戊基、環己基、環庚基、環辛基、苯基、 萘基、聯苯基、第基、菲基、t»比咬基、吱喃基、嘆吩基、 啥啉基、異喹啉基、啡啉基、咔唑基、三畊基或嘧啶基； 心至R44係獨立表示環丙基、環丁基、環戊基、環己基.、 環庚基、環辛基、苯基、萘基、聯苯基、茚基、茱基、苯 并苐基、螺二第基（3卩1]：〇1^1110犷61^1)、蒽基、祐基、菲 基聯伸二本基、丙一稀合第基、α比唆基、咬喃基、π塞吩 基、喹啉基、異喹啉基、啡啉基、咔唑基、笨并呋喃基、 苯并噻吩基、苯并噻唑基、苯并噚唑基、三啡基、嘧啶基Ruler 2, R3, Rs, Re, Re and R9 independently represent hydrazine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, pentyl , hexyl, heptyl, octyl, decyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, hydrazine Phenyl, phenyl, phenanthryl, t» than dimethyl, fluorenyl, stilbene, porphyrin, isoquinolyl, morpholinyl, oxazolyl, tri-pound or pyrimidinyl; heart to R44 Independently means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl., cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, anthracenyl, fluorenyl, benzofluorenyl, snail The first group (3卩1): 〇1^1110犷61^1), fluorenyl, ketone, phenanthrenyl-based two-base, propylene-divalent group, α-indenyl group, thiol group, π-septyl group , quinolyl, isoquinolyl, morpholinyl, oxazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, trimorphinyl, pyrimidinyl

Ri、R4、1^7及R1Q係獨立表示氫、曱基、乙基、正丙基、 95221 13 201204809 異丙基、正丁基、異丁基、第三丁基、戊基、戊烷基、己 基、庚基、辛基、壬基、癸基、三氟甲基、環丙基、環丁 基、環戊基、環己基、環庚基、環辛基、苯基、萘基、聯 苯基、苐基、菲基、吡啶基、呋喃基、噻吩基、喹琳基、 異喹啉基、啡啉基、咔唑基、三哄基或嘧啶基；以及 L"、L12、L21、L22、匕至R,。及r41至r44可進一步經一個 或多個選自氘、（C1-C30)烷基、（C6-C30)芳基、（C1-C30) 烷氧基、氰基、（C1-C30)烷基矽烷基、（C6-C30)芳基矽烷 基'齒（C1-C30)烷基、（C3-C30)雜芳基、（C3-C30)環烷基、 硝基及經基之取代基所取代，但並不限於此。 R41s 只43、 绿 ,Ν-» „ Ν-* Λ^{ 及R44〆可獨立為選自下列結構者，但並不 限於此：Ri, R4, 1^7 and R1Q are independently represented by hydrogen, mercapto, ethyl, n-propyl, 95221 13 201204809 isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, pentyl , hexyl, heptyl, octyl, decyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, hydrazine Phenyl, fluorenyl, phenanthryl, pyridyl, furyl, thienyl, quinolinyl, isoquinolinyl, morpholinyl, oxazolyl, tridecyl or pyrimidinyl; and L", L12, L21, L22, 匕 to R,. And r41 to r44 may further be one or more selected from the group consisting of hydrazine, (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkoxy, cyano, (C1-C30) alkyl矽alkyl, (C6-C30) aryl decyl 'dentate (C1-C30) alkyl, (C3-C30) heteroaryl, (C3-C30) cycloalkyl, nitro and trans-substituent substituted , but not limited to this. R41s only 43, green, Ν-» „ Ν-* Λ^{ and R44〆 can be independently selected from the following structures, but are not limited to this:

其中，among them,

Ru至R35係獨立表示（C1_C30)烷基或⑽_C3〇)芳基或 者心至R35可各自經由具有或不具有稠合環之（C3_C3〇)伸 燒基或（C3-C3G)伸稀基鏈結至相鄰取代基以形成脂環族 環、或單環或多環之芳香環。 更具體而言，本發明之有機電場發光化合物可藉由下 95221 14 201204809Ru to R35 are independently represented by (C1_C30)alkyl or (10)-C3〇)aryl or the core to R35 may each be via a (C3_C3〇)alkyl or (C3-C3G) stretching chain with or without a fused ring. Adjacent substituents form an alicyclic ring, or a monocyclic or polycyclic aromatic ring. More specifically, the organic electroluminescent compound of the present invention can be used by the following 95221 14 201204809

15 95221 20120480915 95221 201204809

16 95221 20120480916 95221 201204809

17 95221 20120480917 95221 201204809

18 95221 20120480918 95221 201204809

19 95221 20120480919 95221 201204809

20 95221 20120480920 95221 201204809

21 95221 20120480921 95221 201204809

22 95221 20120480922 95221 201204809

23 95221 20120480923 95221 201204809

本發明之有機電場發光化合物可參照下列方案1及2 而製備，但其並不限於此。 [方案1]The organic electroluminescent compound of the present invention can be produced by referring to the following Schemes 1 and 2, but it is not limited thereto. [plan 1]

其中，among them,

Ri至R!。、Li、L2、^及Rl2之定義係與化學式1之定義 相同。 本發明提供〆種有機電場發光裝置’其包括第一電 95221 24 201204809 極；第二電極；以及—層或多層插置於該第1極與該第 二電極間之有機層’其中1有機衫括—種或多種化學 式1所示之有機電場發光化合物。 於本發明之有機電場發光裝置中，該有機層可包含電 場發光層’且料場發光層除了包括一種或多種化學式i 所不之有機電場發光化合物作為電場發光軸劑之外，可 進-步包含-種或多種續。應用於本發明切機電場發 光裝置的主體並無特別限制，但可為選自下q 式4或 5者： [化學式4] (AriOl)a-Ll01-(An〇2)b [化學式5] (Ari〇3)c-Li〇2-(An〇4)d 其中，Ri to R!. The definitions of Li, L2, ^ and Rl2 are the same as those defined in Chemical Formula 1. The present invention provides an organic electric field light-emitting device that includes a first electrode 95221 24 201204809 pole; a second electrode; and a layer or layers of organic layers interposed between the first pole and the second electrode, wherein the organic shirt One or more organic electroluminescent compounds of the chemical formula 1 are included. In the organic electric field light-emitting device of the present invention, the organic layer may include an electric field light-emitting layer 'and the material field light-emitting layer may further include, in addition to one or more organic electric field light-emitting compounds of the formula i, as an electric field light-emitting axis. Contains - or more. The body to which the electric field light-emitting device of the cutting machine of the present invention is applied is not particularly limited, but may be selected from the following formula 4 or 5: [Chemical Formula 4] (AriOl) a-Ll01-(An〇2)b [Chemical Formula 5] (Ari〇3)c-Li〇2-(An〇4)d where

Lm表示（C6-C30)伸芳基或（C4_C3〇)伸雜芳基；Lm represents (C6-C30) extended aryl or (C4_C3〇) heteroaryl;

Ll02表示伸蒽基；Ll02 represents a stretching base;

Arm至Arm係獨立表示氫、氘、（cl_C3〇)烷基、（cl_C3〇) 烧氧基、齒素、（C4-C30)雜芳基、（C5-C30)環烧基或（C6-C30) 芳基，且Αη〇ι至An。4之戎環貌基、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所取代：具有 或不具有一個或多個選自具有或不具有鹵素取代基之（C1_ C30)烷基、（C1-C30)烷氧基、（C3-C30)環烷基、鹵素、氰 基、三（C1-C30)烷基矽烷基、二（cl_C3〇)烷基（c6_C3〇)芳 基石夕烧基及二（C6-C30)芳基梦烷基所組成群組之取代基之 95221 25 201204809 (C6-C30)芳基或（C4_C3〇)雜芳 基；具有或不具有齒素取代 基之（C1-C30)烷基；（C1-C30)烷氧基；（C3-C30)環烷基； 齒素；氮基、三（C1-C30)烷基矽烷基；二（C1-C30)烷基 (C6-C30)芳基矽烷基及三（C6_C3〇)芳基矽烷基；以及 a b、c及d係獨立表示〇至4之整數。 電場發光層係指發生電場發光之層，且該層可為單層 或多層’該多層係由兩層或更多層積疊（laminate)而成。 當依據本發明之組成而使用主體-摻雜劑之混合物時，證實 可顯著改善電場發光主體的發光效率。此可藉由使用0.5 至10重量％之摻雜濃度而達成。相較於現存之其它主體材 料’本發明之電場發光主體係提供優異的電洞及電子傳導 性’以及極高的安定性及顯著改善的發光效率及操作壽 命。據此’當選擇化學式4或5所示之化合物作為電場發 光主體時’該化合物可相當程度地彌補本發明之化學式1 所示之化合物的電子缺陷。 有機電場發光裝置可包含化學式1所示之有機電場發 光化合物，也可包含一種或多種選自芳基胺化合物或笨乙 烯基胺化合物所組成群組之化合物。該芳基胺化合物或苯 乙烯基胺化合物之具體實例係提供於韓國專利申請案第 10-2008-0060393號的第&lt;212〉至&lt;224〉段，但其並不限於 此。 於本發明之有機電子裝置中，該有機層除了包含化學 式1所不之有機電場發光化合物外，同時還可進一步包含 -種或多簡自芳基胺化合物及苯乙縣芳基胺化合物二 95221 26 201204809 . 組成群組之化合物。該芳基胺化合物或苯乙烯基芳基胺化 合物係例示於韓國專利申請案第10_2〇〇8_〇123276號第 10-2008-0107606 號或第 10_2008_0118428 號，但其並不 • 限於此。 / 再者，於本發明之有機電場發光裝置中，該有機層除 了包含化學式1所示之有機電場發光化合物外，還可進一 步包含一種或多種選自第1族之有機金屬、第2族、第4 周期與第5周期之過渡金屬、鑭系金屬及d__過渡元素所組 成群組之金屬或錯合物化合物。該有機層可包含電場發光 層及電荷產生層。 可實現具有獨立發光模式的像素結構之有機電場發光 裝置，其中，該有機電場發光裝置係包含本發明之化學式 1所示之有機電場光化合物作為次像素（subpixel)，以及 一種或多種包含選自錶（Ir)、始（Pt)、|£(pd)、姥（Rh)、 銶（Re)、锇（Os)、鉈（ΤΙ)、鉛（Pb)、鉍（Bi)、銦（in)、錫 (Sn)、録（Sb)、碲（Te)、金（Au)及銀（Ag)所組成群組之一 種或多種金屬化合物之次像素（係同時經平行圖案化）。 此外’該有機層除了包含化學式1所示之有機電場發 光化合物外’還可同時包含一層或多層發射藍光、綠光或 紅光的有機電場發光層，以實現發射白光的有機電場發光 裝置。 於本發明之有機電場發光裝置中，可將一層（後文中稱 為「表面層」）選自硫屬化合物（chalcogenide)層、金屬鹵 化物層及金屬氧化物層之層體設置於該電極對的一個或兩 27 95221 201204809 個電極的内表面上。更具體而言’可將矽或鋁之金屬硫屬 化合物（包含氧化物）層設置於該電場發光介質層之陽極表 面上，以及將金屬鹵化物層或金屬氧化物層設置於該電場 發光介質層之陰極表面上。藉此可得到操作安定性。Arm to Arm is independently represented by hydrogen, hydrazine, (cl_C3 〇) alkyl, (cl_C3 〇) alkoxy, dentate, (C4-C30) heteroaryl, (C5-C30) cycloalkyl or (C6-C30) ) aryl, and Αη〇ι to An. The ring, aryl or heteroaryl group may be further substituted with one or more substituents selected from the group consisting of: having or not having one or more substituents selected from the group consisting of having or not having a halogen substituent (C1_C30)alkyl, (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkyldecyl, bis(cl_C3〇)alkyl ( a substituent of the group consisting of an aryl group and a bis(C6-C30) arylcycloalkyl group. 95221 25 201204809 (C6-C30) aryl or (C4_C3〇)heteroaryl; with or without (C1-C30)alkyl having a dentate substituent; (C1-C30) alkoxy; (C3-C30)cycloalkyl; dentate; nitrogen, tri(C1-C30)alkyldecyl; (C1-C30)alkyl (C6-C30) arylalkylene and tris(C6_C3〇)aryldecylalkyl; and ab, c and d are independently represented by an integer of 〇4. The electric field luminescent layer refers to a layer in which electric field luminescence occurs, and the layer may be a single layer or a plurality of layers. The multilayer layer is formed by laminating two or more layers. When a mixture of host-dopant is used in accordance with the composition of the present invention, it is confirmed that the luminous efficiency of the electroluminescent body can be remarkably improved. This can be achieved by using a doping concentration of 0.5 to 10% by weight. Compared to other existing host materials, the electroluminescent main system of the present invention provides excellent hole and electron conductivity&apos; and extremely high stability and significantly improved luminous efficiency and operational life. According to this, when the compound represented by Chemical Formula 4 or 5 is selected as the main body of the electric field, the compound can considerably compensate for the electronic defects of the compound of Chemical Formula 1 of the present invention. The organic electric field light-emitting device may comprise an organic electric field light-emitting compound represented by Chemical Formula 1, and may also contain one or more compounds selected from the group consisting of arylamine compounds or stupidylamine compounds. A specific example of the arylamine compound or the phenylvinylamine compound is provided in paragraphs <212> to <224> of Korean Patent Application No. 10-2008-0060393, but it is not limited thereto. In the organic electronic device of the present invention, the organic layer may further comprise, in addition to the organic electroluminescent compound of the formula 1, and may further comprise one or more simple arylamine compounds and phenylethylamine arylamine compound 2952221 26 201204809 . Compounds that make up the group. The arylamine compound or the styrylarylamine compound is exemplified in Korean Patent Application No. 10-2〇〇8_〇123276, No. 10-2008-0107606 or No. 10_2008_0118428, but it is not limited thereto. Further, in the organic electric field light-emitting device of the present invention, the organic layer may further comprise one or more organic metals selected from the group 1, the second group, in addition to the organic electroluminescent compound of the formula 1. A metal or complex compound of the group consisting of transition metals, lanthanide metals, and d__ transition elements in cycles 4 and 5. The organic layer may include an electric field luminescent layer and a charge generating layer. An organic electric field light-emitting device capable of realizing a pixel structure having an independent light-emitting mode, wherein the organic electric field light-emitting device comprises the organic electric field light compound of Chemical Formula 1 of the present invention as a subpixel, and one or more components selected from the group consisting of Table (Ir), initial (Pt), |£(pd), 姥(Rh), 銶(Re), 锇(Os), 铊(ΤΙ), lead (Pb), bismuth (Bi), indium (in) Sub-pixels of one or more metal compounds of the group consisting of tin (Sn), sb (Sb), strontium (Te), gold (Au), and silver (Ag) (both simultaneously parallel patterned). Further, the organic layer may include one or more organic light-emitting layers emitting blue light, green light or red light in addition to the organic electric field light-emitting compound represented by Chemical Formula 1 to realize an organic electric field light-emitting device that emits white light. In the organic electric field light-emitting device of the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be provided on the electrode pair. One or two of the 27 95221 201204809 electrodes on the inner surface. More specifically, a layer of a metal chalcogenide (including oxide) of ruthenium or aluminum may be disposed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer may be disposed on the field luminescent medium. On the cathode surface of the layer. Thereby, operational stability can be obtained.

該硫屬化合物可為，諸如Si0x(l^X€2^)、AKW1S xS1.5)、Si0N、SiA10N等。該金屬鹵化物可為，諸如[if、The chalcogen compound may be, for example, Si0x (1^X€2^), AKW1S xS1.5), SiON, SiA10N, or the like. The metal halide can be, for example, [if,

MgF2、CaF2、稀土金屬氟化物等。該金屬氧化物可為，諸如MgF2, CaF2, rare earth metal fluoride, and the like. The metal oxide can be, for example

Cs2〇、Li2〇、MgO、SrO、BaO、CaO 等。 於本發明之有機電場發光裝置中，較佳亦可將電子傳 輸化合物與還原性摻雜劑之混合區域、或電洞傳輸化合物 與氧化性推雜劑之混合區域設置於前述所製造之電極對的 至少一表面上。在此實例中，由於電子傳輸化合物被還原 成陰離子，因而使電子變得更容易自混合區域注入及傳輸 至電場發光介質。另外，由於電洞傳輸化合物被氧化成陽 離子，因而使電洞變得更容易自混合區域注入及傳輸至電 場發光介質。較佳的氧化性摻雜劑包含各種路易士酸及受 體化合物（acceptor compound)。較佳的還原性摻雜劑包含 鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬，及其混合 物。再者，可藉由使用還原性摻雜劑層作為電荷產生層來 製造具有兩層或更多層電場發光層之發射白光的電場發光 裝置。 有利效果 由於本發明之有機電場發光化合物展現良好的藍色發 光效率及優異的壽命性質，因此其可用於製造具有極高操 28 95221 201204809 作壽命之0LED裝置。 發明模式 本發明係進一步說明關於本發明之有機電場發光化合 物、該化合物之製備方法、以及使用該化合物之裝置的發 光性質。然而，下列實施例僅提供用於例示性說明用，而 非意欲限制本發明之範圍。 [實施例] [製備例1]化合物2之製備Cs2〇, Li2〇, MgO, SrO, BaO, CaO, and the like. In the organic electroluminescence device of the present invention, it is preferable that 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 the electrode pair manufactured as described above. At least one surface. In this example, since the electron transporting compound is reduced to an anion, it becomes easier for 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 positive ion, the hole becomes more easily 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. Further, an electric field light-emitting device that emits white light having two or more layers of an electroluminescent layer can be fabricated by using a reducing dopant layer as a charge generating layer. Advantageous Effects Since the organic electroluminescent compound of the present invention exhibits good blue light-emitting efficiency and excellent lifetime properties, it can be used for the manufacture of an OLED device having a very high operating life of 28,052,221,0440,809. Mode for Invention The present invention further describes the organic electroluminescent compound of the present invention, a process for preparing the compound, and a light-emitting property of a device using the compound. However, the following examples are provided for illustrative purposes only and are not intended to limit the scope of the invention. [Examples] [Preparation Example 1] Preparation of Compound 2

化合物F之製備 將化合物D( 10公克（g)，16. 99毫莫耳（mmol))溶解於 THFC100毫升（ml))，並在-78°C於其内緩慢加入n-BuLi (50. 99ml，20. 39mmol，2. 5莫耳濃度（Μ)於己烷中）。攪拌 該混合物1小時後，於其内加入DMF(3. 2ml，54. 39mmol)。 缓慢提高溫度後，於室溫下攪拌該混合物12小時。將蒸餾 水加入該混合物並以MC萃取該混合物。以硫酸鎂乾燥並在 減壓下蒸餾後，再經由管柱分離獲得化合物F(4. 7，9.65 mmol, 56· 85%)。 29 95221 201204809 化合物Η之製備 將化合物 G(26g，95. 12mmol)及 NaBH4(5.39g，142.68 mmol)與THF(300ml)混合。於0°C將曱醇缓慢加入該混合 物。2小時後，該混合物以EA萃取及以蒸餾水清洗。以硫 酸鎂乾燥後，再經由管柱分離獲得化合物H(26g，94.42 mmol, 99. 27%)。 化合物I之製備 將化合物H(26g，94.42mmol)溶解於亞磷酸三乙酯 (triethylphosphite)(100ml)中及將破（23. 96g，94. 42 mmo 1)溶解於亞碟酸三乙醋（5Om 1)中。將此兩種溶液緩慢地 混合，並於100°C攪拌。12小時後，使該混合物冷卻至室 溫並在減壓下蒸餾。混合物以MC萃取並以蒸餾水清洗。以 硫酸鎂乾燥及在減壓下蒸餾後，再經由管柱分離獲得化合 物 I(32g，80.92mmol，86.09%) 化合物2之製備 將化合物 F(4. 7g, 9.65mmol)及化合物 1(7. 63g，19. 3 mmol)溶解於THF(50ml)，並於0°C將第三丁醇鉀（24ml， 24. 12mmol, 1. 0M於THF中）加入該混合物中。2小時後， 加入蒸餾水並以MC萃取該混合物。以硫酸鎂乾燥及在減壓 下蒸餾後，再經由管柱分離獲得化合物2(4. 3g，4. 43mmol， 45. 97°/〇) ° [製備例2]化合物101之製備 30 95221 201204809Preparation of Compound F Compound D (10 g (g), 16.99 mmol (mmol)) was dissolved in 100 ml (ml) of THF, and n-BuLi was slowly added thereto at -78 ° C (50. 99 ml, 20.39 mmol, 2.5 mol concentration (Μ) in hexane). After stirring the mixture for 1 hour, DMF (3.2 ml, 54.39 mmol) was added. After slowly increasing the temperature, the mixture was stirred at room temperature for 12 hours. Distilled water was added to the mixture and the mixture was extracted with MC. After drying over magnesium sulfate and distillation under reduced pressure, the compound F (4. 7, 9.65 mmol, 56. 85%) was obtained. 29 95221 201204809 Preparation of the compound hydrazine Compound G (26 g, 95.12 mmol) and NaBH4 (5.39 g, 142.68 mmol) were combined with THF (300 ml). The sterol was slowly added to the mixture at 0 °C. After 2 hours, the mixture was extracted with EA and washed with distilled water. After drying over magnesium sulfate, Compound H (26 g, 94.42 mmol, 99.27%) was obtained. Preparation of Compound I Compound H (26 g, 94.42 mmol) was dissolved in triethylphosphite (100 ml) and the broken (23.96 g, 94.42 mmo 1) was dissolved in triethyl sulphate. 5Om 1). The two solutions were slowly mixed and stirred at 100 °C. After 12 hours, the mixture was cooled to room temperature and distilled under reduced pressure. The mixture was extracted with MC and washed with distilled water. After drying over magnesium sulfate and distillation under reduced pressure, the compound I (32 g, 80.92 mmol, 86.09%) was obtained by the column column. Preparation of Compound 2 Compound F (4.7 g, 9.65 mmol) and Compound 1 (7. 63 g, 19.3 mmol) was dissolved in THF (50 mL) and EtOAc (EtOAc m. After 2 hours, distilled water was added and the mixture was extracted with MC. After drying over magnesium sulfate and distillation under reduced pressure, Compound 2 (4.3 g, 4.43 mmol, 45.97 ° / 〇) was obtained by column separation [Preparation 2] Preparation of Compound 101 30 95221 201204809

化合物L之製備 將二苯胺（20g，118. 2mmol)、化合物 K(24.04g，130.02 mmol)、Pd(0AcM1.3g，5. 91mmol)、碳酸絶（96. 2g，295.50 mmol)及甲苯（500ml)混合後，將三-第三丁基膦（5.8ml， 11.82mmol，於50%二甲苯中）加入並於120°C攪拌。10小 時後，使該混合物冷卻至室溫。將蒸餾水加入混合物，並 以EA萃取該混合物。以硫酸鎂乾燥及在減壓下蒸餾後，再 經由管柱分離獲得化合物L(14. 7g，53.58mmol，45.41%)。 化合物101之製備 以與製備例1之相同方法，使用化合物L作為中間產 物，獲得化合物101(3g，32%)。 [製備例3]化合物106之製備 31 95221 201204809Preparation of Compound L Diphenylamine (20 g, 118. 2 mmol), Compound K (24.04 g, 130.02 mmol), Pd (0 AcM 1.3 g, 5.91 mmol), Carbonic acid (96. 2 g, 295.50 mmol) and toluene (500 ml) After mixing, tri-tert-butylphosphine (5.8 ml, 11.82 mmol in 50% xylene) was added and stirred at 120 °C. After 10 hours, the mixture was allowed to cool to room temperature. Distilled water was added to the mixture, and the mixture was extracted with EA. After drying over magnesium sulfate and distillation under reduced pressure, Compound L (14.7 g, 53.58 mmol, 45.41%) was obtained. Preparation of Compound 101 Compound 101 (3 g, 32%) was obtained in the same manner as in Preparation 1 using Compound L as an intermediate product. [Preparation Example 3] Preparation of Compound 106 31 95221 201204809

化合物Μ之製備 將4-溴曱苯（6.8ml，55.2mmol)加入圓底燒瓶並真空 乾燥後，使該燒瓶充滿氮氣。藉由將THF(200ml)加入該圓 底燒瓶中而將化合物溶解，並冷卻至_78。(：。將正丁基鋰 (22ml，55. 2mmol)緩慢加入該圓底燒瓶後，維持低溫同時 授拌該混合物1小時。1小時後，於_78°c加入菲酿（5g， 24mmol)，並加熱至室溫同時攪拌該混合物3小時。反應完 成後，混合物以乙醚萃取並藉由以硫酸鎂移除剩餘水分而 乾燥。所得材料進行管柱分離，獲得化合物M(5 9g， 14.8ramol, 63%)。 化合物N之製備 將化合物M(5g，12.6mmol)溶解於圓底燒瓶中的Ac〇h (100ml)並於回韻拌1辞（Zn)粉（4g, 63_q1)加入該混 合物》將HCia 5ml)溶解於Ac幫12ml)之溶液加入該圓^ 燒瓶中。30分鐘後，將HC1(2. 5m)溶解於辞粉（ ⑷ 及謂⑽1)之溶液加人該混合物1拌 ） 95221 32 201204809 層色層分析（TLC)無任何反應。混合物以MC、蒸顧水、碳 酸虱鈉溶液及NaC 1溶液萃取，並藉由以硫酸鎂移除剩餘水 分而乾燥。所得物質進行管柱分離，獲得化合物N(4. 3g， 11.9mmol, 97%)。 化合物0之製備 將化合物 N(5.8g，16. lmmol)、NBS(6.6g, 37mmol)及 過氧化苯甲醯（391mg，1. 61mmol)加入圓底燒瓶並真空乾 燥後，使該燒瓶充滿氮氣。待該混合物藉由將cCl4(193ml) 加入該圓底燒瓶而溶解後，於回流攪拌該混合物4小時。 反應完成後，該混合物以MC萃取並藉由以硫酸鎂移除剩餘 水分而乾燥，以繼續下一個反應。 化合物P之製備 將化合物0(llg，21.3mmol)加入圓底燒瓶並真空乾燥 後，使該燒瓶充滿氮氣。待該混合物藉由將亞磷酸三乙酯 (40ml)加入該圓底燒瓶而溶解後，於回流攪拌該混合物7 小時。反應完成後，以蒸餾裝置移除亞磷酸三乙酯。經由 管柱分離而獲得化合物p(l2 2g，19.3匪〇1，91%)。 化合物106之製備 將化合物P(3g，4.75咖〇1)及4-(二苯基胺基）苯曱醛 (3. 1^，11.4mmol)加入圓底燒瓶並真空乾燥後，使該燒瓶 充滿氮氣。待該混合物藉由將THF(2GGml)加人該圓底燒瓶 而/合解並冷部至〇°c後，緩慢加入第三丁醇鉀（57ml, 57mmol)並攪拌1〇分鐘。加熱至室溫後，授摔該混合物（ λ!時反應π成後，該混合物以萃取並藉由以硫酸鎂移 33 95221 201204809 除剩餘水分而乾燥。所得材料進行管柱分離而獲得化合物 106(2g，2.3mmol，50%)。 根據製備例1至3之製程製備有機電場發光化合物1 至111。所製備之有機電場發光化合物之1H NMR及MS/FAB 數據係顯示於表1。 34 95221 201204809 表1 化合物 NMR(CDC13, 200 MHz) MS/FAB 實測值 計算值 X 5 = 6.63 (12Hf m) , 6.81 (4H, m) , 6.95 (4H, m) , 7.2 (8H, m), 7.41(2H, m), 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2H/ m), 8.12(2H, m), 9.09(2H, m) 869.10 868.38 2 δ = 6.63(12H, m), 6.81(4H, m) , 6.95(4H, m), 7.2{8H, m), 7.58-7.59 (6H, m) , 7 · 73~7.7*7 ( 6H, m) , 7.92 (2H, m), 7.98-8(6H, m)r 8.12(2H, m), 9.09(2H, m) 969.22 968.41 3 δ = 6.63 (12H, m) , 6.81(4H, m) , 6.95 (4H, m) f 7.2(8H, m&gt;, 7.55(4H/ m), 7.61(2H, m)f 7.77(4H, m) , 7.98-8.12(8H, m), 8·42(2Η, m), 8.55(2H, m}, 9.09(2H, m) 969.22 968.41 4 δ = 6.63(12Η, m), 6.81 (4H, m), 6.95 (4H, in), 7.2-7.25 (16H, m)f 7.41(2H, m), 7.51-7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H/ m), 9.09(2Hr m) 1021.29 1020.44 5 δ = 6.63(12Η, m), 6.81(4H, m&gt;, 6.95(4H, m), 7.2〜7.25(16H, m), 7.58-7.59(6H, m), 7.73-7.77(6H, m)f 7.92(2Η, m), 7.98-8(6H, m), 8.12(2H, m), 9.09(2H, m) 1121.41 1120.48 6 δ = 2.34(6H, s), 6.63(12H, m) f 6.8K4H, m), 6.95(4H, rt〇, 7.2&lt;8H, rr〇, 7.29~7.33(8H, m), 7.77(4H, m), 7.98&lt;2H, m), 8.12(2H, m), 9.09(2H, m) 897.15 896.41 7 δ = 6.63 (12H, m), 6,81 (4H, m) , 6.95 (4Hf m), 7.2 (8H, m), 7.3(4H/ m), 7.39(4H, m), 7.77(4H, m) , 7.98(2H, m), 8.12(2H, m), 9.09(2Hf m) 905.08 904.36 β δ = 3.83(6H, s), 6·63(12Η, in), 6.81(4H, 6.95(4H, m), 7.05(4H, m), 7.2(8H, m) , 7.68(4H, m) , 7.77(4H, m) f 7.98(2H, m), 8.12(2H, m)f 9.09(2H, m) 929.15 928.40 9 δ = 6.63(12H, m) , 6.81(4H, m) , 6.95(4H, m), 7.2(8H, ra), 7.77(4H, m), 7.98'7.99(6Hf m), 8.12(2H/ m), 8.75(4Hr m), 9.09(2H, m) 871.08 870.37 10 δ = 6.63(12Η, m), 6.81 (4H, m), 6.95{4Hf m), 7.17-7.2 (10H, m), 7.4(2H, m), 7.69(2H, m), 7.77(4H, m), 7.98(2H, ra), 8.12(2H, m), 9.09(2Hf m) 881.16 880.29 11 δ = 6.63(8Hf m), 6.81(4H, m) # 6.95~6- 98 (6H, m), 7.2(8H, 7·41(2Η, m), 7.51~7_54(12H, m), 7·73(2Η, m), 7.87(2H, m), 7.98(2H, m) , 8.07-8.12(4H, m), 9.09(2H, m) 969.22 968.41 12 δ = 6.63(8H, m), 6.81(4Hf m) , 6.95(4H, m) f 7.2(8H, m), 7.41 (2H, m) , 7.49-7.57(14H, m) , 7.74(2H, m), 7.83~7.84(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 969.22 968.41 13 δ = 6.63( 8H, m), 6,69(4H, in), 6.81(4Hr m), 6.95 (4H, m), 7.2(8H, m) , 7.4K2H, ra) f 7.51-7.56 {16H, m), 7.64(4H, m)f 7.98(2H, m)f 8.12(2H/ m), 9.09(2H, m) 1021.29 1020.44 14 δ = 0.9(12H, m), 1.91(8H, m), 6.58-6.63 (10H, m) f 6.75-6.81(6H, m), 6.95(4H, m) , 7.2(8H, m) , 7.41(2H, m) f 7·51~7.54(10Η, m), 7·62(2Η, m), 7·71(2Η, m), 7.87(2H, m), 7_98(2H, m), 8·12(2Η, m), 9·09(2Η, m&gt; 1157.53 1156.57 15 δ = 1.51(8H, m)r 2.09(8Hf m) f 6.58-6.63 (10Hf m), 6.75-6.8K6H, m), 6.95(4H, πι) , 1.2(QH, m) , 7.41(2H, m) f 7.51'7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, 1153.49 1152.54 35 95221 201204809 τι), 7.98(2Η, m), 8.12(2Η, m) , 9.09(2Η, m) 16 δ = 1.48(12Hf m)# 2.02(8Η, m) , 6.58-6.63 (1〇Η, m), 6.75-6.8K6H, m), 6.95(4Η, m) , 7.2(8Η, ra), 7.4K2H, m), 7.51-7.54(10Η, m), 7.62(2Η, m)# 7.71(2Η, m) , 7.87(2Η, m), 7.98(2Η, m), 8.12(2Η, m), 9.09(2Η, m) 1181.55 1180.57 17 δ = 3.49(8Η, s), 6.58'6.63(10Η# rn), 6.75~6.81 (6Η, m), 6.95(4Η, m), 7.2(16Η, m) , 7.41(2Η, m), 7.51-7.54(10Η, m&gt;, 7.62(2Η, m) , 7.71(2Η, m) , 7.87(2Η, m), 7.98(2Η, m), 8·12(2Η, π〇, 9.09(2Η, m) 1249.58 1248.54 18 δ= 6.63(8Η, m) , 6.75-6.81(8Η, m), 6.95(4Η, m), 7.08(2Η, m) , 7·2(8Η, ιη), 7 · 38~7 · 52 (18Η, m) , 7.58 (4Η, m), 7·94~7·98(4Η, m), 8.12(2Η, π〇, 8·59(2Η, m), 9·09(2Η, m) 1199.48 1198.50 19 δ = 0·66(12Η, s), 6·63(8Η, m), 6·69&lt;2Η, m), 6.81(4Η, τι), 6.95-6.99(6Η, m), 7.2(8Η, m) , 7.27(2Η, m), 7.4K2H, ί\), 7.51~7.56(12Hf m) , 7.98(2Η/ m), 8.12^8.17 (4Η, m), 9.09{2Η, ιη) 1133.57 1132.46 20 δ = 6.63(8Η, ιτι), 6.79-6.81 (8Η, m) , 6.95(4Hf m) , 7.2(8Η/ m), 7.37-7.55(30Η, m), 7.64-7.66(4Η, m) , 7.76(2Η, m), 7.Θ9(2Η, m), 7.98(2Η, m), 8.12(2Η, m), 9.09(2Η, π\) 1381.85 1380.52 21 δ = 1.3(8Η, m), 1.45(8Η, m) , 6.63 (8Η, m), 6.79-6.81(8Η, m), 6.95(4Η, m), 7·2(8Η, m), 7.41(2Η, m), 7.5卜7·52(8Η, m), 7.64-7.66(4Η, m) , 7.76(2Hf m), 7.89 (2Η, m), 7.98(2Η/ m), 8·12(2Η, m), 9·09(2Η, m) 1185.64 1184.49 22 δ = 6.63(8Η, m) , 6.81(4Η, m&gt;, 6.95(4Η, π〇 , 7·08(2Η, m), 7.2(8Η, m), 7.32{2Η, m) , 7.41{2Η, m), 7.5卜7.52(8Η, m), 7.71(4Hf m), 7.98-8.04(4Η, m), 8.12(2Η, m), 8.28(2Η, m), 8.68(2Η, in), 8.93(2Hf in), 9.09(2Η, m) 1069.34 1068.44 23 δ = 6.63(8Η, m), 6.81(4Hf m), 6.91-6.95 (6H, m) , 7.2(8Hf τι), 7.41(2H, m), 7.51-7.52 (8H, m) , 7.82'7.88 (4H, m), 7·98(4Η, m), 8.12(6H, m), 8.93&lt;2H, m), 9·09(4Η, m&gt; 1069.34 1068.44 24 δ = 6.63(8H, m) , 6.81(4H, m) , 6.96(2H, 7.2(10H, m), 7.41-7.56 (14H, rn), 7.69(2^, m), 7.86(2H, m), 8.07(2H, τ〇, 8·97(2Η, m) 871.08 870.37 25 δ = 6.63(8H, m), 6.7(2H, m), 6.81(4H, m) # 6.95(4Η, m), 7.2(8H, m), 7.41-7.52(12H, m), 7.86~7.88(4H, m), 8·07(2Η, m), 8·97(2Η, m) 871.08 870.37 26 δ-6.63(8Η, m), 6.81(4H, m), 6.95-6.99 (4Hf m) , 7.2{8H, m) , 7.4K2H, m), 7.51-7.52 (8H, m), 7.86(2H/ m), 8.07(2H, n) f 8.36(2H# s), 8.61(2H, s), 8.97(2H, m) 873.05 872.36 27 δ = 6.63(8H, m), 6.81(4H, m), 6.95-6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51-7.52(8H, m), 7.86(2Hf m), 8.07(2H, m), 8.33(2H, s) , 8.97(2H, m) 875.03 874.35 36 95221 201204809 28 δ = 6.63(8Η, m), 6.81(4Η, m) f 6.95(4Η, m) f 7.2(8H, m), 7.41〜7.43(4H, m), 7.5卜7.56(10H, m}, 7·98(2Η, m), 8.12(2H, m), 8.32(2H, m), 8.68(2H, m) , 8.82(2H, m), 9.09(2H, m) 971.19 970.40 29 δ = 6.63(8Hf m), 6.81(4H, m) , 6.95(4H, m), 7.2(8H/ in), 7.33 (2H, m) , 7.41(2H# m), 7.51~7.52(8H, m), 7.86-7.9(4H, m), 8·07(2Η, m), 8·38(2Η, m), 8.71(2H, m), 8.88(2H, m), 8.97(2H, m) 971.19 970.40 30 δ = 6.63(8H, m), 6·81(4Η, n〇 , 6.95&lt;4H, m&gt;, 7.12(2H, m), 7.2(8Hf m), 7.41(2H, m) , 7.51-7.52(8H, m) , 7.72(2Hf m), 7.83〜7.86(4H,m&gt;,8.07(2H,m&gt;,8.25(2H,m&gt;,8.5(2H,m), 8.97(4H, m) 1073.29 1072.43 31 δ = 6.63(8Hr m), 6.8-6.81(6H, m) , 7.2(10H, m), 7.28(2H, m), 7.41(2Hf m) , 7.51-7.58(12H, m) f 7.86(2H, m), 8.01(2H, m), 8·07(2Η, m), 8·38(2Η, m), 8.83(2H, m), 8.97(2H, m) 1073.29 1072.43 32 δ = 6.3(2H, m), 6.63(8H, m) f 6.81{4H, m) , 6.9-6.99{6Hf m), 7.2(8H, m), 7.41(2H, m) , 7.51-7.52(8Hf m) , 7.86(2H, m) , 8.07(2Η, m), 8.97(2Η, m) 881.16 880.29 33 δ = 6.54(2H, m), 6.63(8H, m), 6.81(4H, m) , 6.95-7(6H, m) , 7.2 (8H, m&gt;, 7.41(2H, m), 7.5卜7·52(8H, m) , 7.86(2H, m)f 8.07(2H, m), 8.97(2H, m) 849.02 848.34 34 δ = 6.29(8H, m), 6.59(2H, s), 6.81-6.85(8H, m) , 7.14(2H, s), 7.2(8H, m), 7.41{2H, m) , 7.51-7.52 (8H, m) , 7.86(2H, m), 8.07(2H, m), 8.97(2H/ m) 974.95 976.18 35 δ = 6.63(8Hf m), 6.81(4H, m) , 6.95-6.99(4H, m) , 7.2(8H, m) , 7.41(2H, m) , 7.51-7.52(8H, m) , 7.86(2H, m) , 8.07(2H, m), 8.97(2H, m) 885.11 884.28 36 δ = 6.63(8Η, m), 6.81{4H, m) , 6.95-6.99 (4H, m), 7.2(8H, m) , 7.41(2H, m), 7.51-7.52(8H, m), 7.86(2Hf m) , 8.07(2H, ίπ), 8.97(2H, m) 852.98 852.32 37 δ = 5.67(2H, m), 6.29 (8H, m) , 6·79〜6.81(6H, m&gt;, 7.2&lt;8H, m), 7.41(2H, m), 7.51-7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 978.90 980.16 38 δ = 6.63(8Hf m) , 6.81(4H, m) , 6.88(2H, m), 6.95(4H, m), 7.2(8H/ m), 7.41(2H, m) , 7.51-7.52(8H, m), 7.59{2H, m), 7·98(2Η, m), 8.12(2H, m), 8.74(4H, m), 9.09(2Hr m) 973.17 972.39 39 δ = 1.72(12H, s), 3.2(6H, s) , 5.66(2H, m) , 5.87(2H, m), 6.45(2H, m), 6.63(8H, m), 6.81-6.83(6H, m), 6.95(4H, m), 7.07-7.08 (4H, m), 7.2(8H, m), 7·41(2Η, m), 7-51〜7·52(8Η, m), 7·98(2Η, m), 8.12(2H, m), 9·09(2Η, m) 1159.50 1158.56 40 δ = 3.2(6H, s), 5.7(2H, m) , 5.9K2H, m) , 6.49(2H, m), 6.63-6.6 7(10H, m), 6.81(4H, m) , 6.92~6.95(6H, m), 7.13(2H, m), 7.2(8H, m) , 7.41(2H, m) , 7.51-7.52(8H, m), 1107.34 1106.46 37 95221 201204809 7·98(2Η, m), 8·12(2Η, m), 9.09(2H, m) 41 5 = 3.2(6Hf s), 5.74(2Η, m), 5.95(2H# m) , 6.53{2Hf in), 6·63(8Η, m&gt;, 6·81~682(6H, m), 6.95'6·97(6H, m), 7·2〜7·22(10Η,π〇, 7.41(2H, m) , 7·51~7·52(8H, n〇 , 7.98{2H, m), 8.12(2H/ m), 9.09(2H, m) 1233.26 1234.30 42 δ = 3.2(6Η, s) , 5.88(2H, m) , 6.47(2H, m) , 6.63(8H, m), 6.81-6.84(6H, m) , 6.91^6.95(8H, m) , 7.16^7.2(10H, m), 7.4K2H, m), 7.51-7.52 (8H, m), 7.98{2H, m), 8.12(2H, m)f 9.09(2H, m) 1139.47 1138.41 43 δ = 2.88(8H, m), 3.2(6H, s) f 5.69(2H, m), 5.9(2H, m), 6.48(2H, m), 6.63(8H, m), 6.81-6.82(6H, m), 6.95(4H, m), 7.07-7.1 (4H, m) , 7.2(8H, m) , 7.41 (2H, m), 7.51-7,52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1131.45 1130.53 44 δ = 3.2(6H, s), 5.74(2H/ m), 5.95(2H, m), 6.53(2H, m), 6·63(8Η,π〇,6.81〜6.82(6Η,π〇,6.95〜7.03(10Η,π〇, 7.2(8Hr m), 7.28(2H/ m) , 7.41(2Hf m) , 7.51-7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1127.42 1126.50 45 δ = 3.2(6H, s) , 5.8(2H, m), 6.01(2H, m), 6.59-6.63(10H, m), 6.81(4H, m), 6.88(2H, m) , 6.95(4H, m) # 7.2(8H, m)# 7.32(2H, n〇, *7.41 〜7·57&lt;16Η, π〇, 7.85MH, m), 7.98(2H, Ή), 8_12(2H, m), 9_09(2H, m) 1227.54 1226.53 46 δ = 1.16(8H, m), 1.48&lt;4H, m), 1·58&lt;8Η, 2.57(2H, m), 6.6(4Hf m), 6.77(2H, m), 6.95(4H, m), 7.23(4H, m), 7.33(4H, m), 7.41(2H, m), 7.51-7.52(8H, m) , 7.8(4H, m), 7.98(2H, m), 8.12(2Hf m), 9.09(2H, m) 881.20 880.48 47 δ = 1·16(16Η, m), 1.48(8H, m), 1.58(16H, m), 2.57(4H, m), 6.76(4Hf m), 6.95(4H, m), 7.41(2H, m), 7.51-7.52(8H, m), 7·84(4Η, m&gt;, 7.98(2H, m), 8·12(2Η, m)r 9.09(2H, m) 893,29 892.57 48 δ = 1.76 (40H, m) , 1·87(8Η, m), 2.1(8H, m), 2.89(4H, m), 6.76(4H, m), 6.95(4H, m) , 7.41(2H, ra) , 7.51-7.52(8H, m), 7·84(4Η, m), 7·98(2Η, m), 8·12(2Η, m), 9.09&lt;2H, n〇 1101.59 1100.69 49 δ = 6·63(4Η, m), 6.95(4H, m) , 7.36-7.41(6H, m), 7.49-7.52(16H, m) , 7.74-7.77(12H, m) , 7.84-7.88 (8H, m), 7.98(2H, m), 8.12(2H, m)f 9.09(2H/ m) 1069.34 1068.44 50 δ = 6.63(8H, m), 6.8K2H, m) , 6.95(4H, m), 7.2 (4H, m), 7.36^7.41(4H, m), 7.49~7.52 (12H, m), 7.74-7.77(8H, m) f 7.84~7.88(4H, m&gt;, 7.98&lt;2H, 8·12(2Η, m), 9·09(2Η, m) 969.22 968.41 51 δ = 6.63(4H, m), 6.95-6.98(8H, m), 7.38-7.41(6H, m), 7·51~*7·57(20Η, m), 7·77(4Η, m), 7.98 〜8.12(12H, m), 9.09(2Η, m) 1069.34 1068.44 38 95221 201204809 52 δ = 6.63(8Η, m), 6.81(2Η, m&gt;, 6.95-6.98(6Η, m) f 7.2(4Η, m), 7.38-7.4K4H, m) , 7.51^7.57 (14H, m) , 7.77(4H, m), 7.98-8.12(8Hr m), 9.09(2Η, m) 969.22 968.41 53 δ = 6.63(4H, m), 6.69(8H, m) r 6.95(4H, m) f 7.41(6H, m), 7.51-7.54(32H, m) , 7.77(4H, m)f 7.98(2H, m), 8.12(2Η, m), 9.09(2H, m) 1173.48 1172.51 54 δ = 6.63(8Hr m), 6.81(2H, m) , 6.95(4H, m)f 7.2(4H, m), 7.38-7.4K10H, m), 7.51-7.52 (8H, m), 7.77-7.8(6H, m) f 7.88-7.9(8H, m) f 7.98(2Η, m) f 8.12(2H, m), 9.09(2H, m) 1069.34 1068.44 55 δ = 6.63(8Hf m), 6.81(2Hf m), 6.95(4Hf m) , 7.08(2Hf m), 7.2(4H, m), 7.32(2H, m) , 7.41(2H, m) , 7.51-7.52(8H# m), 7.71-7.88(12H, m), 7.98(2H, m), 8.12(4H, m) , 8.68(2H, m), 8.93(2H, m)r 9.09(2H, m) 1069.34 1068.44 56 δ = 6.63(4H, m) , 6.95(4Hf m)f 7.08(4Hf m), 7.32(4H, m), 7.41(2H, m), 7.51-7.52(8Hf m) , 7.71-7.88(20H, m), 7.98(2H, m), 8.12(6H, m), 8.68(4H, m), 8.93(4H, m), 9.09(2H, m) 1269.57 1268.51 57 δ = 6.63 (8Hr m), 6.81 (2H, in), 6.91-6.95 (6H, m) f 7.2 (4H, m)f 7.41(2H, m), 7.51〜7·52(8H, m) , 7.77-7.88(12H, m), 7.98(2Hf m), 8.12(6H, m), 8.93(4H/ m), 9.09(2H, m) 1069.34 1068.44 58 δ = 6.63{8H, m) , 6.81(2H, m), 6.95(4H/ m) , 7.02(2H, m), 7.2(4H, m), 7.41(2H, m), 7.51-7.52(8H, m), 7.71-7.88(14H, m) , 7.98(2H, m) , 8.12-8.13(6Hf m), 8.93(2H, m), 9.09(2H/ m) 1069.34 1068.44 59 δ = 6.63 (8H, m), 6.81 (2H, m), 6.91〜6.95(6H, m) , 7.2(4H, m), 7.4K2H, m), 7.51-7.52 ( 8H, m) , 7.71-7.88 (16H, m), 7.98(2H, m), 8.12(6H, m), 9.09&lt;2H, in) 1117.38 1116.44 60 δ = 6.63(8H, m), 6·81(2Η, m), 6·95(4Η, m&gt;, 7·2(8Η, rr〇, 7.41(2H, m), 7.51-7.52(8H, m) , 7.71~7.82(14H, m), 7.98-8{6H, m), 8.12(2H, m) , 9.09(2Hf m) 1117.38 1116.44 61 δ = 6.63( 4H, m), 6 ·95( 4H, n〇, 7.02( 4H, π〇, 7·41( 2H, 7-51〜7.52(8H, m), 7.77〜7·88&lt;24Η, m), 7·98&lt;2Η, n〇, 8.12-8.13 (14H, m), 8.93(8H, m), 9.09(2H, m) 1469.80 1468.57 €2 δ = 6.63 (8H, m) , 6.81(4H, m) , 6.95(4H, m) f 7.2(4H, m), 7.41(2Hf m), 7.51-7.57(10H, m), 7.73-7.78(8H, m), 7.88(2H, m&gt;, 7.98(2H, rr〇, 8.卜8.12(6H, m&gt;, 8.42(4H, m), 9.09(2H, m) 1X17.38 1116.44 63 δ = 6.63(4Hf m), 6.95(4H, m), 7.12(2H, m) , 7.41(2H, m), 7.51-7.58(16H, m), 7.72-7.77(6H, m), 7.83(2H, m), 7·94~7·98(4Η, m), 8.12(2H, m), 8.22-8.25 (4Hf m), 8.38(4H/ m), 8.83(4H, m) , 9.09{2H, m) 1277.47 1276.47 €4 δ = 0.9(24H, m) , 1.91(16Hf m), 6.58-6.63(8H, m) , 6.75(4Hf m), 6.95{4H, m) , 7·28(4Η, m), 7.38〜7·41 (6H, m), 7.51-7.55(12H, m)r 7.62(4H, m), 7.77(4H/ m), 7.87(4H, ί\), 7.98(2Η, m), 8.12(2H/ m) , 9.09(2H, m) 1445.95 1444.76 39 95221 201204809 65 δ = 0·9(12Η, m), 1_91(8Η, π〇, 6·58 〜6.63U0H, π〇, 6.75〜6.81(4Η, ιτ〇, 6·95(4Η, m), 7·2(4Η, m), 7.28(2H, n〇, 7.38-7.4Κ4Η, m) , 7.51^7.55 {10Η, m), 7.62(2Η, m), 7·77(4Η, π〇, 7·87(2Η, m), 7·98(2Η, π〇, 8.12(2Η, m), 9·09(2Η, m) 1157.53 1156.57 66 δ = 0.9 (12Η, m), 1.91(8Η, m) , 6.47(2Η, s), 6.63 (8Η, m), 6.81{2Η, m), 6.95 (4Η, m)r 7·2〜7·24(6Η, m), 7.41-7.52(16Η, m) , 7.6K2H, m) , 7.77(4Η, τη) , 7.98(2Η, m), 8·08~8·12(6Η, m), 8·46(2Η, π〇, 9·09(2Η, π〇 1257.64 1256.60 67 δ = 0.9 (24Η, τη) , 1.91-1.93 (16Η, m) , 6.63 (4Η, m) , 6.77 (3Η, m), 6.95(4Η, m) , 7.18(3Hf m) , 7·24~7·29(5Η, m), 7.41-7.52(15Hf m) Γ 7.61(4Η, m) , 7.71-7.77(11Η, m) # 7.85(1Η, m), 7.98-8.02(5Η, m) , 8·09〜8·16(7Η, m), 9.09(2Η, m) 1646.19 1644.82 68 δ = 6.58'6.63(10Hf m), 6.75-6.81(4Η, m), 6.95(4Η, m), 7.11 (8Η, m) , 7.2-7.41 (22Η, m) , 7.51-7.55 (10Η, ιη), 7_62(2Η, π〇, 7·77&lt;4Η, m), 7·87(2Η, m), 7.98(2Η, m), 8.12(2Η, m), 9.09(2Η, m) 1349.70 1348.57 69 δ = 6.39 (2Η# m) , 6.55(2Η, ιτι) , 6 · 63 (8Η, m&gt;, 6 · 81 (2Η, ιτ〇 , 6.95(4Η, m) , 7.16-7.2 (8Η, m), 7.28(4Η, m) , 7.35~7.41(8Η, m), 7.5-7.55(14Hf m), 7.75-7.77(6Η, m), 7.87(4Η, m), 7.98(2Η, m), 8.12{2Η, m), 9.09(2Η/ m) 1345.67 1344.54 70 δ = 5·19(4Η, s), 6.39(2Η, τη), 6.5K2H, m) , 6.63(8Η, m), 6.81(2Η, m), 6.95(4Η, m) f 7.03-7.06(10Η, m&gt;, 7.15'7.2(12H, m), 7.4K2H, m) , 7.51-7.52 ( 8H, m), 7,77(4H, m), 7·98(2Η, m), 8·12(2Η, π〇, 9·09(2Η, m&gt; 1221.53 1220.51 71 δ = 5.19( 4H, s), 6.39( 2H, m&gt;, 6.51( 2H, m), 6.63( 8H, n〇, 6.81(2H, m) , 6.95(4H, m), 7·03〜7·06(10H, m), 7.15-7.2(12H, m), 7.41(2H, m) , 7.51-7.52(8H, m), 7.77(4H, π〇, 7·98&lt;2Η, m&gt;, 8·12(2Η, π〇, 9.09(2H, ir〇 1221.53 1220.51 72 δ = 6.62〜6.63(8H, m) , 6.7(4H, π〇 , 6.95{4H, m) , 7.41(2H, m) , 7.51-7.55(12H, m) , 7.77(4H, m), 7.98(2H, m), 8.07~8.12(6H, m), 9.09(2H, m) 873.05 872.36 73 δ = 6·62~6·63(6H, m), 6.95(4H, m) , 7.19(2H, m), 7.37-7.41(8Hf m) , 7.51-7.57(10H, m) , 7.69-7.8(10H, m), 7.94-7.98(4H, m), 8.12(2H/ m), 8.22(2Η, m), 8.75(2H/ m), 9.09(2H, m) 1073.29 1072.43 74 δ = 6.95(4H, m), 7.25'7.33(6H, m), 7.41(2H, m), 7.5-7.52 (14H, m), 7.62-7.63(6H, m), 7.94-7.98 (4H, m)t 8.12(4H, m), 8.55(2H, m), 9.09(2H, m) 865.07 864.35 75 δ = 1.72(12H, s), 6.55(4H/ m) , 6.63(4H, m) , 6.73(4H, m)t 6.95(4H, m) f 7.02-7.05{8H, m) r 1.4H2H, m) t 7.51〜7.52(8H, m), 7·77(4Η, m), 7.98(2H, n〇, 8·12(2Η, m), 9.09(2H, m) 949.23 948.44 40 95221 201204809 76 δ = 6·38(8Η, π〇, 6.56(8Η, π〇, 6·63(8Η, m), 6,81(2Η, π〇, 6.95(4Η, m), 7.2(4Η, m) , 7.41(2Η, τη), 7.51-7.52 (8Η, m), 7·77(4Η, π〇, 7·98(2Η, m), 8.12(2Η, m), 9·09(2Η, m&gt; 1047.29 1046.43 77 δ = 6.63(4Hf m)f 6.95-6.97(8Η, m), 7.16-7.21(12Η, m), 7.41(2Hf m), 7.51-7.52(8Hf m)f 7.77(4H, m), 7.98(2H, τ〇, 8·12(2Η, m》，9_09(2H, m) 929.20 928.29 78 δ = 6.59-6.63(8Hf m), 6.77(4Hf m)r 6.89-6.95(12H, m), 7.4K2H, m), 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2Hf m), 8.12(2H, m), 9.09(2H, m) 897.07 896.34 79 δ = 6·63 (4H, m) , 6.73(8H, m), 6.95(4H/ m) , 7.2K4H, m), 7.3(4H, m), 7.37-7.55(30H, m), 7.77(4H, m), 7.98(2H, ί\) , 8.12(2H, m), 9.09(2Hf m) 1229.66 1228.46 80 δ = 1.3(8H, m), 1.45(8Η, m), 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(4H, m), 7·3(4Η, m), 7·41(2Η, m), 7.5卜7·52(8Η, ro), 7.77(4H, 7·98(2Η, ir〇, 8·12(2Η, τι), 9.09(2H, m) 1033.45 1032.43 81 δ = 2.71(8H, s), 6.63(4H, m), 6.73(8H, m) , 6.95(4H, m), 7·1卜7.14(8H, m), 7.21&lt;4H, m), 7.3(4H, π〇, 7·41(2Η, m), 7.51-7.52(8H, m), 7.77(4H, m)f 7.98(2H, m), 8.12{2H, m), 9.09(2H, m) 1129.54 1128.43 82 δ = 2.88(8Η, m&gt;, 6.58〜6.63(8H, m&gt;, 6.76(4H, m), 6.95(4H, τι), 7.02-7.04(8Hr m) , 7.41{2Hf m) , 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 921.18 920.41 83 δ = 6.63 (8H, m), 6.81 (4H, m&gt;, 6.95〜7 ·05( 12H, m), *7.25 (4H, m) , 7.41 (2H, , 7·5卜7 · 52 (8H, m) , 7.77 HH, m) , 7.98 (2H, r 8.12(2Hf m), 9.09(2Hf m) 917.14 916.38 84 δ = 6.63(4H, m) , 6.69(4H, m), 6.87(4H, m), 6.95(4H, m), 7.16(4Η, m), 7.41-7.54{18H, m), 7.77(4Hf m), 7.85(4H, m), 7·98(2Η, m), 8·12(2Η, m), 9·09(2Η, m) 1017.26 1016.41 85 δ = 1.53(12Η, m), 3.63 (4H, m), 5.99-6.05 (8H, m), 6.95(4H, 7.22〜7_33(16H, m), 7·41(2Η, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1077.40 1076.51 86 δ = 6.63(4Η, m), 6.95&lt;4H, m), 7.14(4H, m), 7.32-7.41(10H, m), 7·51〜7·52(8Η, m&gt;, 7·66(4Η, m), 7·77(4Η, m), 7.89(4H, m), 7.98(2H, m), 8.12{2H, m)f 9.09(2Hf m) 1029.18 1028.36 87 δ = 6.63{8Hf m) , 6.81(2H, ro), 6.95(4H/ m) f 7.14(2H, m), 7.2(4H, m) f 7.32-7.41(6H, m) , 7.51-7.52(8H, m) , 7,66(2H, m), 7.77(4H, m), 7.89(2H, m), 7·98(2Η, m), 8·12(2Η, m), 9.09(2H# m) 949.14 948.37 88 δ = 6.34(4Hr m), 6.63(4H, m) r 6.95(4H, m) , 7.41(2H, m) r 7.5-7.52(16H, m), 7.77~7.79(8H, m)f 7.98(6H, m), 8.12(2H, m), 9.09(2Hf m) 1093.45 1092.27 89 δ = 6·63(8Η, ir〇, 6.81(2H, m&gt;, 6·95(4ΗΓ m), 7.2(4H, m), 7.4K2H, m), 7.51^7.53 (12H, m), 7.77(4Η, m), 7.98-8.01(4H, m), 8.12(2H, m), 8.18{2H, m)f 9.09(2H, 983.25 982.32 41 95221 201204809 m) 90 δ = 6.63(4H, m), 6.95(4H, m), 7.39-7.41(10H, m), 7·51〜7.52(8H, m)r 7·74~7·77(12Η, m), 7·98(2Η, m), 8.12(2H, m), 9.09(2H, m) 1033.14 1032.34 91 δ = 1.35{36H, si, 6.55 (8Hf m), 6.63 (4H, m), 6.95-7.0K12H, m), 7.41(2H, m), 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m) , 9.09(2H, m) 1093.53 1092.63 92 δ =* 0.25 (36H, s), 6.61 〜6.63U2H, m), 6.95(4H, m), 7.15{8Hf m), 7.4K2H, m) , 7.51-7.52 (8H, m) , 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1157.83 1156.54 93 δ = 6.63 (4H, m), 6.73 (8H, m) , 6.95 (4Hf in), 7.21 (8H, m), 7.37-7.55 (70H, m), 7.77(4Hf m) , 7.98(2H, m) , 8.12(2H, m), 9.09(2H, m) 1902.66 1900.73 94 δ = 6.61~6·63(12Η, 6.95-6.99(12H, m) , 7·41(2Η, m&gt;, 7.51-7.52(8H, m) , 7.77(4H, m) , 7.98(2H, m), 8.12(2H, τι), 9·09(2Η, m&gt; 941.06 940.34 95 δ = 6·56(8Η, m), 6.63( 4H, m), 6.95( 4H, m), 7.37~7_41&lt;l〇H, rr〇, 7:51~7·52(8Η, m), 7.77(4H, m), 7·98(2Η, m), 8_12(2H, m), 9.09(2H, m) 1141.09 1140.33 96 δ = 6.63(4Η, m), 6.81(8H, m), 6.95(4H, m)f 7.39-7.41 (10H, m) , 7.51-7.52 (8H, m) , 7.77(4H, m) , 7.98(2H, m) , 8.12(2H, m), 9.09(2H, m) 969.14 968.36 97 δ = 3·83(12Η, s), 6.52(8H, 6·63(4Η, m), 6.74(8H, m),6.95(4H,m),7.41(2H,m),*7.51〜7.52(8H,ir〇,7.77(4H, m), 7·98(2Η, m), 8·12(2Η, m), 9.09(2H, m) 989.20 988.42 98 δ = 6.63(8H, m), 6.69{4Η, m) , 6.81(2H, m&gt;, 6.95(4Hf m), 7.2(4H, m), 7.41(4Hf m), 7.51-7.54 (20H, m), 7.77(4H, m), 7.98(2H, m)# 8.12(2Hr m), 9.09(2H, m) 1021.29 1020.44 99 δ = 6.62-6.63 (8H, m) , 6.7(4Hf m), 6.95(4H, m) , 7.41(2H# m), 7.51-7.55(12H, m), 7.77(4H, m), 7.98(2H, m), 8.07'8.12{6H# m), 9.09(2H, m) 873.05 872.36 100 δ = 6.63(4H, m), 6.95(4H, m), 7.27{4H, m) f 7.36*7.41(6Hf m), 7.51'7.52(8H, m) , 7.77{4H, m)f 7.98~8.12(12H, m), 9.09(2H, m) 873.05 872.36 101 δ = 6.63(8H, m), 6.7(2Hf m) , 6.81(4H, m) , 6.95(4H, m), 7.2(8H, ro), 7·46(2Η, π〇, 7·58~7.59(6Η, m), 7'73&lt;2H, m), 7.86-7.92 (6H, m), 8(4H, m), 8.07(2H, m), 8.91(2Hf m) 971.19 970.40 102 δ = 6.63 (8H, m), 6.81 (2H, m), 6.95(4Hf m) , 7.2(4H/ m) f 7.4K2H, m), 7.51-7.52 (8H, m) , 7.77(4H, m) , 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 879.16 878.44 103 δ = 3.05(4H, m), 4.14(4H, m) , 6.55-6.6(6H, m), 6.72(2H, m), 6·95(4Η, m), 7·05〜7.07(4H, ra) , 7·41(2Η, m), 7.51-7.52(8H, m), 7.8(4H, m) , 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 768.98 768.35 42 95221 201204809 104 7.41(2«, m)；7'5lT；2^H (47H«m&gt;，7*〇5'7-〇7(4H， 8.12(2H, m)&gt; 9.〇9(2h, m；，，7-8&lt;4H&gt;mK7-98&lt;2^ 825,09 824.41 105 U('25h2 .41(2H, rn), 7.5~7.52(12H, m), 7.6~7.62(6H mi 7.93~7.98(6H, ra), 8.i2(2H, m), 9.09(2H. ’ 764.95 764.32 106 7 &quot;；H1(4H，m)，6-95&lt;^〇7TTr8H, m)； 7.56(4H, m), 7.64(4H, m), 7.77~7.88(8H, m) 8 12(?H m), 8.93(2H, m) ,叫，8.12(2H, 869.10 858.38 107 7. -7.= = ^ 7.56〜7.59(6H, &lt; 7.69(2H, m&gt;, l·— «-93(2«, m) 871.08 870.37 108 1 H, m)i ^.ϋ1!4Η, in), 6.96(2H, π〇 &quot;T2iS» mi 7.45~7.49(4H, 7 ，7.2 (8H, m), 8 12f2H 〇 ' 7'69(2H^ m)^ 7-81~7.88(1〇h, m), 8.：12J2H, m)t 8-85(2H, m), 8.93f2H. 873.05 872.36 109 7 41(2H Ί b.al(4H,和，6·95(4Η，m)，7.2&lt;8H, &quot;»&gt;, I) 8 U2H V 7,56(12H，7·64(4^ 7.77(4H, &gt;f 8·1(2Η» 8.34(2H, m), 8.99(2Hr 1021.29 1020.44 110 δ — 6.63( 12HP m) c PlfiltT m\ r~~nT--- 7.4K2H, m), 7.51~7.56{12H, m), 7.64(4H, m) 7 77,4« …8:叫2H, m), 8·18(2η, ( q 7.77HH， 1021.29 1020-44 111 5;~7 8· ~ · Τ、7·64&lt;4Η,叫，7·77〜7·88 咖⑴， B.U/ o.i^(6H, m), 8.93(2H, m) 873.05 872.36 [實施例1至11]使用本發明之有機電場發光化合物 之0LED裝置的製造 使用本發明之有機電場發光材料製造〇LED裝置。首 先，使用超音波依序以三氯乙烯、丙酮、乙醇及蒸餾水洗 滌取自0LED(Samsung Corning製造）用玻璃之透明電極ιτο 薄膜（15 Ω /□)，並儲存於異丙醇中備用。然後，將【το基 板裝配於真空氣相沈積裝置之基板夾中，並將4,4，，4，，_ 參（N，N-(2-萘基）-苯基胺基）三苯胺（2-TNATA)置於該真空 氣相沈積裝置之一小室（cell)中，並將該小室通風達1〇-6 托（torr)真空。接著，對該小室施加電流以蒸發2-TNATA， 從而在該ΙΤ0基板上形成厚度為60奈米（nm)之電洞注入 層0 95221 43 201204809 接著，將Ν，Ν’-雙（α-萘基）-Ν，Ν’-二苯基-4, 4’-二胺 (ΝΡΒ)置於該真空氣相沈積裝置之另一小室中，對該小室施 加電流以蒸發ΝΡΒ，從而於該電洞注入層上形成厚度為20 nm之電洞傳輸層。 形成電洞注入層及電洞傳輸之後，以下列方式於其上 形成電場發光層。將MA(實施例1至3)置於真空氣相沈積 裝置之一小室中作為主體，並將本發明之化合物置於另一 小室中作爲摻雜劑。以100 : 3之速率氣相沈積此兩種材 料，從而於該電洞傳輸層上形成厚度為30 nm之電場發光 層0Preparation of the compound hydrazine After adding 4-bromoindolebenzene (6.8 ml, 55.2 mmol) to a round bottom flask and vacuum drying, the flask was filled with nitrogen. The compound was dissolved by adding THF (200 ml) to the round bottom flask and cooled to _78. (: After n-butyllithium (22 ml, 55.2 mmol) was slowly added to the round bottom flask, the mixture was stirred for 1 hour while maintaining a low temperature. After 1 hour, phenanthrene (5 g, 24 mmol) was added at _78 ° C. The mixture was stirred for 3 hours while heating to room temperature. After the reaction was completed, the mixture was extracted with diethyl ether and dried by removing residual water with magnesium sulfate. The obtained material was subjected to column separation to obtain compound M (5 9 g, 14.8 ramol , 63%). Preparation of Compound N Compound M (5 g, 12.6 mmol) was dissolved in Ac〇h (100 ml) in a round bottom flask and added to the mixture in a mixture of Zn powder (4 g, 63_q1). A solution of HCia 5 ml) dissolved in Ac (12 ml) was added to the round flask. After 30 minutes, a solution of HC1 (2.5 m) dissolved in the powder ((4) and (10) 1) was added. The mixture was mixed 1) 95221 32 201204809 No color reaction (TLC). The mixture was extracted with MC, steamed water, sodium bismuth carbonate solution and NaC 1 solution, and dried by removing the remaining water with magnesium sulfate. The obtained material was subjected to column chromatography to obtain Compound N (4.3 g, 11.9 mmol, 97%). Preparation of Compound 0 Compound N (5.8 g, 16.1 mmol), NBS (6.6 g, 37 mmol) and benzamidine peroxide (391 mg, 1.61 mmol) were placed in a round bottom flask and dried in vacuo. . After the mixture was dissolved by adding cCl 4 (193 ml) to the round bottom flask, the mixture was stirred under reflux for 4 hours. After the reaction was completed, the mixture was extracted with MC and dried by removing residual water with magnesium sulfate to continue the next reaction. Preparation of Compound P After compound 0 (llg, 21.3 mmol) was placed in a round bottom flask and dried under vacuum, the flask was filled with nitrogen. After the mixture was dissolved by adding triethyl phosphite (40 ml) to the round bottom flask, the mixture was stirred at reflux for 7 hours. After the reaction was completed, triethyl phosphite was removed by a distillation apparatus. Compound p (12 g, 19.3 匪〇 1, 91%) was obtained by column separation. Preparation of Compound 106 Compound P (3 g, 4.75 Curry 1) and 4-(diphenylamino)benzofural (3.11, 11.4 mmol) were added to a round bottom flask and dried under vacuum to fill the flask. Nitrogen. After the mixture was added to the round bottom flask by THF (2 GGml) and then cooled to &lt;RTI ID=0.0&gt;&gt;&gt; After heating to room temperature, the mixture was dropped (when λ!, the reaction was π, the mixture was extracted and dried by removing the remaining moisture with magnesium sulfate 33 95221 201204809. The obtained material was subjected to column separation to obtain compound 106 ( 2 g, 2.3 mmol, 50%). Organic electroluminescent compounds 1 to 111 were prepared according to the procedures of Preparation Examples 1 to 3. The 1H NMR and MS/FAB data of the prepared organic electroluminescent compound are shown in Table 1. 34 95221 201204809 Table 1 Compound NMR (CDC13, 200 MHz) MS/FAB calc. calculated value X 5 = 6.63 (12Hf m) , 6.81 (4H, m) , 6.95 (4H, m) , 7.2 (8H, m), 7.41 (2H , m), 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2H/ m), 8.12(2H, m), 9.09(2H, m) 869.10 868.38 2 δ = 6.63(12H, m ), 6.81(4H, m), 6.95(4H, m), 7.2{8H, m), 7.58-7.59 (6H, m) , 7 · 73~7.7*7 ( 6H, m) , 7.92 (2H, m ), 7.98-8(6H, m)r 8.12(2H, m), 9.09(2H, m) 969.22 968.41 3 δ = 6.63 (12H, m) , 6.81(4H, m) , 6.95 (4H, m) f 7.2(8H, m&gt;, 7.55(4H/m), 7.61(2H, m)f 7.77(4H, m) , 7.98-8.12(8H, m), 8·42(2Η, m), 8.55(2H, m}, 9.09(2H, m) 969.22 968.41 4 δ = 6. 63(12Η, m), 6.81 (4H, m), 6.95 (4H, in), 7.2-7.25 (16H, m)f 7.41(2H, m), 7.51-7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H/m), 9.09(2Hr m) 1021.29 1020.44 5 δ = 6.63(12Η, m), 6.81(4H, m&gt;, 6.95(4H, m), 7.2~ 7.25(16H, m), 7.58-7.59(6H, m), 7.73-7.77(6H, m)f 7.92(2Η, m), 7.98-8(6H, m), 8.12(2H, m), 9.09( 2H, m) 1121.41 1120.48 6 δ = 2.34(6H, s), 6.63(12H, m) f 6.8K4H, m), 6.95(4H, rt〇, 7.2&lt;8H, rr〇, 7.29~7.33(8H, m), 7.77(4H, m), 7.98&lt;2H, m), 8.12(2H, m), 9.09(2H, m) 897.15 896.41 7 δ = 6.63 (12H, m), 6,81 (4H, m ), 6.95 (4Hf m), 7.2 (8H, m), 7.3 (4H/m), 7.39(4H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2Hf m) 905.08 904.36 β δ = 3.83(6H, s), 6·63(12Η, in), 6.81(4H, 6.95(4H, m), 7.05(4H, m), 7.2(8H, m) , 7.68(4H, m) , 7.77(4H, m) f 7.98(2H, m), 8.12(2H, m)f 9.09(2H, m) 929.15 928.40 9 δ = 6.63(12H, m) , 6.81(4H , m), 6.95(4H, m), 7.2(8H, ra), 7.77(4H, m), 7.98'7.99(6Hf m), 8.12(2H/m), 8.75(4Hr m), 9.09(2H, m) 871.08 870.37 10 δ = 6.63 (12Η, m), 6. 81 (4H, m), 6.95{4Hf m), 7.17-7.2 (10H, m), 7.4(2H, m), 7.69(2H, m), 7.77(4H, m), 7.98(2H, ra), 8.12(2H, m), 9.09(2Hf m) 881.16 880.29 11 δ = 6.63(8Hf m), 6.81(4H, m) # 6.95~6- 98 (6H, m), 7.2(8H, 7·41(2Η , m), 7.51~7_54(12H, m), 7.73(2Η, m), 7.87(2H, m), 7.98(2H, m) , 8.07-8.12(4H, m), 9.09(2H, m 969.22 968.41 12 δ = 6.63(8H, m), 6.81(4Hf m) , 6.95(4H, m) f 7.2(8H, m), 7.41 (2H, m) , 7.49-7.57(14H, m) , 7.74 (2H, m), 7.83~7.84(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 969.22 968.41 13 δ = 6.63( 8H, m), 6,69 (4H, in), 6.81(4Hr m), 6.95 (4H, m), 7.2(8H, m) , 7.4K2H, ra) f 7.51-7.56 {16H, m), 7.64(4H, m)f 7.98( 2H, m)f 8.12(2H/m), 9.09(2H, m) 1021.29 1020.44 14 δ = 0.9(12H, m), 1.91(8H, m), 6.58-6.63 (10H, m) f 6.75-6.81 ( 6H, m), 6.95(4H, m) , 7.2(8H, m) , 7.41(2H, m) f 7·51~7.54(10Η, m), 7·62(2Η, m), 7·71( 2Η, m), 7.87(2H, m), 7_98(2H, m), 8·12(2Η, m), 9·09(2Η, m&gt; 1157.53 1156.57 15 δ = 1.51(8H, m)r 2.09( 8Hf m) f 6.58-6.63 (10Hf m), 6.75-6.8K6H, m), 6.95 (4H, ι) , 1.2(QH, m) , 7.41(2H, m) f 7.51'7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, 1153.49 1152.54 35 95221 201204809 τι ), 7.98(2Η, m), 8.12(2Η, m) , 9.09(2Η, m) 16 δ = 1.48(12Hf m)# 2.02(8Η, m) , 6.58-6.63 (1〇Η, m), 6.75 -6.8K6H, m), 6.95(4Η, m) , 7.2(8Η, ra), 7.4K2H, m), 7.51-7.54(10Η, m), 7.62(2Η, m)# 7.71(2Η, m) , 7.87(2Η, m), 7.98(2Η, m), 8.12(2Η, m), 9.09(2Η, m) 1181.55 1180.57 17 δ = 3.49(8Η, s), 6.58'6.63(10Η# rn), 6.75~ 6.81 (6Η, m), 6.95(4Η, m), 7.2(16Η, m), 7.41(2Η, m), 7.51-7.54(10Η, m&gt;, 7.62(2Η, m) , 7.71(2Η, m) , 7.87(2Η, m), 7.98(2Η, m), 8·12(2Η, π〇, 9.09(2Η, m) 1249.58 1248.54 18 δ= 6.63(8Η, m) , 6.75-6.81(8Η, m) , 6.95(4Η, m), 7.08(2Η, m) , 7·2(8Η, ιη), 7 · 38~7 · 52 (18Η, m) , 7.58 (4Η, m), 7·94~7· 98(4Η, m), 8.12(2Η, π〇, 8·59(2Η, m), 9·09(2Η, m) 1199.48 1198.50 19 δ = 0·66(12Η, s), 6·63(8Η , m), 6·69 &lt;2Η, m), 6.81(4Η, τι), 6.95-6.99(6Η, m), 7.2(8Η, m) , 7.27(2Η, m), 7.4K2H, ί\), 7. 51~7.56(12Hf m) , 7.98(2Η/ m), 8.12^8.17 (4Η, m), 9.09{2Η, ιη) 1133.57 1132.46 20 δ = 6.63(8Η, ιτι), 6.79-6.81 (8Η, m) , 6.95(4Hf m) , 7.2(8Η/ m), 7.37-7.55(30Η, m), 7.64-7.66(4Η, m) , 7.76(2Η, m), 7.Θ9(2Η, m), 7.98( 2Η, m), 8.12(2Η, m), 9.09(2Η, π\) 1381.85 1380.52 21 δ = 1.3(8Η, m), 1.45(8Η, m) , 6.63 (8Η, m), 6.79-6.81 (8Η , m), 6.95(4Η, m), 7·2(8Η, m), 7.41(2Η, m), 7.5 Bu 7·52(8Η, m), 7.64-7.66(4Η, m) , 7.76(2Hf m), 7.89 (2Η, m), 7.98(2Η/ m), 8·12(2Η, m), 9·09(2Η, m) 1185.64 1184.49 22 δ = 6.63(8Η, m) , 6.81(4Η, m&gt;, 6.95 (4Η, π〇, 7·08(2Η, m), 7.2(8Η, m), 7.32{2Η, m), 7.41{2Η, m), 7.5.7.52(8Η, m), 7.71 (4Hf m), 7.98-8.04(4Η, m), 8.12(2Η, m), 8.28(2Η, m), 8.68(2Η, in), 8.93(2Hf in), 9.09(2Η, m) 1069.34 1068.44 23 δ = 6.63(8Η, m), 6.81(4Hf m), 6.91-6.95 (6H, m) , 7.2(8Hf τι), 7.41(2H, m), 7.51-7.52 (8H, m) , 7.82'7.88 ( 4H, m), 7·98(4Η, m), 8.12(6H, m), 8.93&lt;2H, m), 9·09(4Η, m&gt; 1069.34 1068.44 24 δ = 6.63(8H, m) , 6.81(4H, m) , 6.96(2H, 7.2(10H, m), 7.41-7.56 (14H, rn), 7.69(2^, m), 7.86(2H, m), 8.07(2H, τ 〇, 8·97(2Η, m) 871.08 870.37 25 δ = 6.63(8H, m), 6.7(2H, m), 6.81(4H, m) # 6.95(4Η, m), 7.2(8H, m), 7.41-7.52(12H, m), 7.86~7.88(4H, m), 8·07(2Η, m), 8·97(2Η, m) 871.08 870.37 26 δ-6.63(8Η, m), 6.81(4H , m), 6.95-6.99 (4Hf m) , 7.2{8H, m) , 7.4K2H, m), 7.51-7.52 (8H, m), 7.86(2H/ m), 8.07(2H, n) f 8.36( 2H# s), 8.61(2H, s), 8.97(2H, m) 873.05 872.36 27 δ = 6.63(8H, m), 6.81(4H, m), 6.95-6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51-7.52(8H, m), 7.86(2Hf m), 8.07(2H, m), 8.33(2H, s) , 8.97(2H, m) 875.03 874.35 36 95221 201204809 28 δ = 6.63(8Η, m), 6.81(4Η, m) f 6.95(4Η, m) f 7.2(8H, m), 7.41~7.43(4H, m), 7.5 b 7.56(10H, m}, 7 · 98 (2Η, m), 8.12(2H, m), 8.32(2H, m), 8.68(2H, m) , 8.82(2H, m), 9.09(2H, m) 971.19 970.40 29 δ = 6.63(8Hf m), 6.81(4H, m), 6.95(4H, m), 7.2(8H/in), 7.33 (2H, m), 7.41(2H# m), 7.51~7.52(8H, m), 7.86-7.9 (4H, m), 8·07(2Η, m), 8·38(2Η, m), 8. 71(2H, m), 8.88(2H, m), 8.97(2H, m) 971.19 970.40 30 δ = 6.63(8H, m), 6.81(4Η, n〇, 6.95&lt;4H, m&gt;, 7.12 (2H, m), 7.2 (8Hf m), 7.41 (2H, m), 7.51-7.52 (8H, m), 7.72 (2Hf m), 7.83~7.86 (4H, m&gt;, 8.07 (2H, m&gt;, 8.25(2H,m&gt;,8.5(2H,m), 8.97(4H, m) 1073.29 1072.43 31 δ = 6.63(8Hr m), 6.8-6.81(6H, m) , 7.2(10H, m), 7.28(2H , m), 7.41(2Hf m) , 7.51-7.58(12H, m) f 7.86(2H, m), 8.01(2H, m), 8·07(2Η, m), 8·38(2Η, m) , 8.83(2H, m), 8.97(2H, m) 1073.29 1072.43 32 δ = 6.3(2H, m), 6.63(8H, m) f 6.81{4H, m) , 6.9-6.99{6Hf m), 7.2( 8H, m), 7.41(2H, m) , 7.51-7.52(8Hf m) , 7.86(2H, m) , 8.07(2Η, m), 8.97(2Η, m) 881.16 880.29 33 δ = 6.54(2H, m ), 6.63(8H, m), 6.81(4H, m), 6.95-7(6H, m), 7.2 (8H, m&gt;, 7.41(2H, m), 7.5 b 7·52(8H, m) , 7.86(2H, m)f 8.07(2H, m), 8.97(2H, m) 849.02 848.34 34 δ = 6.29(8H, m), 6.59(2H, s), 6.81-6.85(8H, m) , 7.14( 2H, s), 7.2(8H, m), 7.41{2H, m), 7.51-7.52 (8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H/ m) 974.95 976.18 35 δ = 6.63(8Hf m), 6.81(4H, m) , 6 .95-6.99(4H, m) , 7.2(8H, m) , 7.41(2H, m) , 7.51-7.52(8H, m) , 7.86(2H, m) , 8.07(2H, m), 8.97(2H , m) 885.11 884.28 36 δ = 6.63(8Η, m), 6.81{4H, m) , 6.95-6.99 (4H, m), 7.2(8H, m) , 7.41(2H, m), 7.51-7.52(8H , m), 7.86(2Hf m) , 8.07(2H, ίπ), 8.97(2H, m) 852.98 852.32 37 δ = 5.67(2H, m), 6.29 (8H, m) , 6.79~6.81 (6H, m&gt;, 7.2 &lt;8H, m), 7.41(2H, m), 7.51-7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 978.90 980.16 38 δ = 6.63(8Hf m) , 6.81(4H, m) , 6.88(2H, m), 6.95(4H, m), 7.2(8H/ m), 7.41(2H, m) , 7.51-7.52(8H, m ), 7.59{2H, m), 7·98(2Η, m), 8.12(2H, m), 8.74(4H, m), 9.09(2Hr m) 973.17 972.39 39 δ = 1.72(12H, s), 3.2 (6H, s), 5.66(2H, m), 5.87(2H, m), 6.45(2H, m), 6.63(8H, m), 6.81-6.83(6H, m), 6.95(4H, m), 7.07-7.08 (4H, m), 7.2(8H, m), 7·41(2Η, m), 7-51~7·52(8Η, m), 7·98(2Η, m), 8.12(2H , m), 9·09(2Η, m) 1159.50 1158.56 40 δ = 3.2(6H, s), 5.7(2H, m) , 5.9K2H, m) , 6.49(2H, m), 6.63-6.6 7(10H , m), 6.81(4H, m) , 6.92~6.95(6H, m), 7.13(2H, m), 7.2(8H, m) , 7.41(2H, m) , 7.51-7.52(8H, m), 1107.34 1106.46 37 95221 201204809 7·98(2Η, m), 8·12(2Η, m), 9.09(2H, m) 41 5 = 3.2 (6Hf s), 5.74(2Η, m), 5.95(2H# m) , 6.53{2Hf in), 6·63(8Η, m&gt;, 6.81~682(6H, m), 6.95'6·97 (6H, m), 7·2~7·22 (10Η, π〇, 7.41(2H, m), 7·51~7·52(8H, n〇, 7.98{2H, m), 8.12(2H/ m), 9.09(2H, m) 1233.26 1234.30 42 δ = 3.2(6Η, s) , 5.88(2H, m) , 6.47(2H, m) , 6.63(8H, m), 6.81-6.84(6H, m) , 6.91^6.95(8H, m) , 7.16^7.2(10H, m), 7.4K2H, m), 7.51-7.52 (8H, m), 7.98{2H, m), 8.12(2H, m)f 9.09( 2H, m) 1139.47 1138.41 43 δ = 2.88(8H, m), 3.2(6H, s) f 5.69(2H, m), 5.9(2H, m), 6.48(2H, m), 6.63(8H, m) , 6.81-6.82(6H, m), 6.95(4H, m), 7.07-7.1 (4H, m) , 7.2(8H, m) , 7.41 (2H, m), 7.51-7,52(8H, m) , 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1131.45 1130.53 44 δ = 3.2(6H, s), 5.74(2H/ m), 5.95(2H, m), 6.53(2H , m), 6·63 (8Η, π〇, 6.81~6.82 (6Η, π〇, 6.95~7.03 (10Η, π〇, 7.2(8Hr m), 7.28(2H/ m), 7.41(2Hf m) , 7.51-7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H , m) 1127.42 1126.50 45 δ = 3.2(6H, s) , 5.8(2H, m), 6.01(2H, m), 6.59-6.63(10H, m), 6.81(4H, m), 6.88(2H, m ), 6.95(4H, m) # 7.2(8H, m)# 7.32(2H, n〇, *7.41 ~7·57&lt;16Η, π〇, 7.85MH, m), 7.98(2H, Ή), 8_12( 2H, m), 9_09(2H, m) 1227.54 1226.53 46 δ = 1.16(8H, m), 1.48&lt;4H, m), 1·58&lt;8Η, 2.57(2H, m), 6.6(4Hf m), 6.77(2H, m), 6.95(4H, m), 7.23(4H, m), 7.33(4H, m), 7.41(2H, m), 7.51-7.52(8H, m) , 7.8(4H, m) , 7.98(2H, m), 8.12(2Hf m), 9.09(2H, m) 881.20 880.48 47 δ = 1·16(16Η, m), 1.48(8H, m), 1.58(16H, m), 2.57( 4H, m), 6.76(4Hf m), 6.95(4H, m), 7.41(2H, m), 7.51-7.52(8H, m), 7·84(4Η, m&gt;, 7.98(2H, m), 8·12(2Η, m)r 9.09(2H, m) 893,29 892.57 48 δ = 1.76 (40H, m) , 1·87(8Η, m), 2.1(8H, m), 2.89(4H, m ), 6.76(4H, m), 6.95(4H, m), 7.41(2H, ra) , 7.51-7.52(8H, m), 7·84(4Η, m), 7·98(2Η, m), 8·12(2Η, m), 9.09&lt;2H, n〇1101.59 1100.69 49 δ = 6·63(4Η, m), 6.95(4H, m) , 7.36-7.41(6H, m), 7.49-7.52( 16H, m) , 7.74-7.77(12H, m) , 7.84-7.88 (8H, m), 7.98(2H, m ), 8.12(2H, m)f 9.09(2H/ m) 1069.34 1068.44 50 δ = 6.63(8H, m), 6.8K2H, m) , 6.95(4H, m), 7.2 (4H, m), 7.36^7.41 (4H, m), 7.49~7.52 (12H, m), 7.74-7.77(8H, m) f 7.84~7.88(4H, m&gt;, 7.98&lt;2H, 8·12(2Η, m), 9·09 (2Η, m) 969.22 968.41 51 δ = 6.63(4H, m), 6.95-6.98(8H, m), 7.38-7.41(6H, m), 7·51~*7·57(20Η, m), 7 · 77(4Η, m), 7.98~8.12(12H, m), 9.09(2Η, m) 1069.34 1068.44 38 95221 201204809 52 δ = 6.63(8Η, m), 6.81(2Η, m&gt;, 6.95-6.98(6Η m) f 7.2(4Η, m), 7.38-7.4K4H, m) , 7.51^7.57 (14H, m) , 7.77(4H, m), 7.98-8.12(8Hr m), 9.09(2Η, m) 969.22 968.41 53 δ = 6.63(4H, m), 6.69(8H, m) r 6.95(4H, m) f 7.41(6H, m), 7.51-7.54(32H, m) , 7.77(4H, m)f 7.98( 2H, m), 8.12(2Η, m), 9.09(2H, m) 1173.48 1172.51 54 δ = 6.63(8Hr m), 6.81(2H, m) , 6.95(4H, m)f 7.2(4H, m), 7.38-7.4K10H, m), 7.51-7.52 (8H, m), 7.77-7.8(6H, m) f 7.88-7.9(8H, m) f 7.98(2Η, m) f 8.12(2H, m), 9.09 (2H, m) 1069.34 1068.44 55 δ = 6.63(8Hf m), 6.81(2Hf m), 6.95(4Hf m) , 7.08(2Hf m), 7.2(4H, m), 7.32(2H, m) , 7.41(2H, m) , 7.51-7.52(8H# m), 7.71-7.88(12H, m), 7.98(2H, m), 8.12(4H, m) , 8.68(2H, m), 8.93(2H m)r 9.09(2H, m) 1069.34 1068.44 56 δ = 6.63(4H, m) , 6.95(4Hf m)f 7.08(4Hf m), 7.32(4H, m), 7.41(2H, m), 7.51- 7.52(8Hf m) , 7.71-7.88(20H, m), 7.98(2H, m), 8.12(6H, m), 8.68(4H, m), 8.93(4H, m), 9.09(2H, m) 1269.57 1268.51 57 δ = 6.63 (8Hr m), 6.81 (2H, in), 6.91-6.95 (6H, m) f 7.2 (4H, m)f 7.41(2H, m), 7.51~7·52(8H, m) , 7.77-7.88(12H, m), 7.98(2Hf m), 8.12(6H, m), 8.93(4H/ m), 9.09(2H, m) 1069.34 1068.44 58 δ = 6.63{8H, m) , 6.81( 2H, m), 6.95(4H/m), 7.02(2H, m), 7.2(4H, m), 7.41(2H, m), 7.51-7.52(8H, m), 7.71-7.88(14H, m) , 7.98(2H, m) , 8.12-8.13(6Hf m), 8.93(2H, m), 9.09(2H/ m) 1069.34 1068.44 59 δ = 6.63 (8H, m), 6.81 (2H, m), 6.91~ 6.95(6H, m) , 7.2(4H, m), 7.4K2H, m), 7.51-7.52 ( 8H, m) , 7.71-7.88 (16H, m), 7.98(2H, m), 8.12(6H, m ), 9.09 &lt;2H, in) 1117.38 1116.44 60 δ = 6.63(8H, m), 6·81(2Η, m), 6·95(4Η, m&gt;, 7·2(8Η, rr〇, 7.41( 2H, m), 7.51-7.52 (8H, m) , 7.71~7.82(14H, m), 7.98-8{6H, m), 8.12(2H, m) , 9.09(2Hf m) 1117.38 1116.44 61 δ = 6.63( 4H, m), 6 ·95( 4H, n 〇, 7.02( 4H, π〇, 7·41( 2H, 7-51~7.52(8H, m), 7.77~7·88&lt;24Η, m), 7·98&lt;2Η, n〇, 8.12-8.13 ( 14H, m), 8.93(8H, m), 9.09(2H, m) 1469.80 1468.57 €2 δ = 6.63 (8H, m) , 6.81(4H, m) , 6.95(4H, m) f 7.2(4H, m ), 7.41(2Hf m), 7.51-7.57(10H, m), 7.73-7.78(8H, m), 7.88(2H, m&gt;, 7.98(2H, rr〇, 8.b 8.12(6H, m&gt;, 8.42(4H, m), 9.09(2H, m) 1X17.38 1116.44 63 δ = 6.63(4Hf m), 6.95(4H, m), 7.12(2H, m) , 7.41(2H, m), 7.51-7.58 (16H, m), 7.72-7.77(6H, m), 7.83(2H, m), 7.94~7.98(4Η, m), 8.12(2H, m), 8.22-8.25 (4Hf m), 8.38(4H/m), 8.83(4H, m) , 9.09{2H, m) 1277.47 1276.47 €4 δ = 0.9(24H, m) , 1.91(16Hf m), 6.58-6.63(8H, m) , 6.75( 4Hf m), 6.95{4H, m) , 7·28(4Η, m), 7.38~7·41 (6H, m), 7.51-7.55(12H, m)r 7.62(4H, m), 7.77(4H / m), 7.87(4H, ί\), 7.98(2Η, m), 8.12(2H/ m) , 9.09(2H, m) 1445.95 1444.76 39 95221 201204809 65 δ = 0·9(12Η, m), 1_91 (8Η, π〇 , 6·58 ～6.63U0H, π〇, 6.75~6.81 (4Η, ιτ〇, 6·95(4Η, m), 7·2(4Η, m), 7.28(2H, n〇, 7.38-7.4Κ4Η, m) , 7.51^7.55 {10Η, m), 7.62(2Η, m), 7·77(4Η, π〇, 7·87(2Η, m), 7·98(2Η, π〇, 8.12(2Η, m), 9·09(2Η, m) 1157.53 1156.57 66 δ = 0.9 (12Η, m), 1.91(8Η, m) , 6.47(2Η, s), 6.63 (8Η, m), 6.81{2Η, m) , 6.95 (4Η, m)r 7·2~7·24(6Η, m), 7.41-7.52(16Η, m) , 7.6K2H, m) , 7.77(4Η, τη) , 7.98(2Η, m), 8·08~8·12(6Η, m), 8·46(2Η, π〇, 9·09(2Η, π〇1257.64 1256.60 67 δ = 0.9 (24Η, τη) , 1.91-1.93 (16Η, m) , 6.63 (4Η, m), 6.77 (3Η, m), 6.95(4Η, m), 7.18(3Hf m) , 7·24~7·29(5Η, m), 7.41-7.52(15Hf m) Γ 7.61 (4Η, m) , 7.71-7.77(11Η, m) # 7.85(1Η, m), 7.98-8.02(5Η, m) , 8·09~8·16(7Η, m), 9.09(2Η, m) 1646.19 1644.82 68 δ = 6.58'6.63(10Hf m), 6.75-6.81(4Η, m), 6.95(4Η, m), 7.11 (8Η, m), 7.2-7.41 (22Η, m), 7.51-7.55 (10Η , ιη), 7_62(2Η, π〇, 7·77&lt;4Η, m), 7·87(2Η, m), 7.98(2Η, m), 8.12(2Η, m), 9.09(2Η, m) 1349.70 1 348.57 69 δ = 6.39 (2Η# m) , 6.55(2Η, ιτι) , 6 · 63 (8Η, m&gt;, 6 · 81 (2Η, ιτ〇, 6.95(4Η, m) , 7.16-7.2 (8Η, m ), 7.28(4Η, m), 7.35~7.41(8Η, m), 7.5-7.55(14Hf m), 7.75-7.77(6Η, m), 7.87(4Η, m), 7.98(2Η, m), 8.12 {2Η, m), 9.09(2Η/ m) 1345.67 1344.54 70 δ = 5·19(4Η, s), 6.39(2Η, τη), 6.5K2H, m) , 6.63(8Η, m), 6.81(2Η, m), 6.95(4Η, m) f 7.03-7.06(10Η, m&gt;, 7.15'7.2(12H, m), 7.4K2H, m) , 7.51-7.52 ( 8H, m), 7,77(4H, m ), 7·98(2Η, m), 8·12(2Η, π〇, 9·09(2Η, m&gt; 1221.53 1220.51 71 δ = 5.19( 4H, s), 6.39( 2H, m&gt;, 6.51( 2H , m), 6.63( 8H, n〇, 6.81(2H, m) , 6.95(4H, m), 7·03~7·06(10H, m), 7.15-7.2(12H, m), 7.41(2H , m) , 7.51-7.52(8H, m), 7.77(4H, π〇, 7·98&lt;2Η, m&gt;, 8·12(2Η, π〇, 9.09(2H, ir〇1221.53 1220.51 72 δ = 6.62 ~6.63(8H, m) , 6.7(4H, π〇, 6.95{4H, m) , 7.41(2H, m) , 7.51-7.55(12H, m) , 7.77(4H, m), 7.98(2H, m ), 8.07~8.12(6H, m), 9.09(2H, m) 873.05 872.36 73 δ = 6·62~6·63(6H, m), 6.95(4H, m) , 7.19(2H, m), 7 .37-7.41(8Hf m) , 7.51-7.57(10H, m), 7.69-7.8(10H, m), 7.94-7.98(4H, m), 8.12(2H/m), 8.22(2Η, m), 8.75(2H/m), 9.09(2H, m) 1073.29 1072.43 74 δ = 6.95(4H, m), 7.25'7.33(6H, m), 7.41(2H, m), 7.5-7.52 (14H, m), 7.62-7.63(6H, m), 7.94-7.98 (4H, m)t 8.12(4H, m), 8.55(2H, m), 9.09(2H, m) 865.07 864.35 75 δ = 1.72(12H, s), 6.55(4H/ m) , 6.63(4H, m) , 6.73(4H, m)t 6.95(4H, m) f 7.02-7.05{8H, m) r 1.4H2H, m) t 7.51~7.52(8H, m ), 7·77(4Η, m), 7.98(2H, n〇, 8·12(2Η, m), 9.09(2H, m) 949.23 948.44 40 95221 201204809 76 δ = 6·38(8Η, π〇, 6.56 (8Η, π〇, 6·63(8Η, m), 6,81(2Η, π〇, 6.95(4Η, m), 7.2(4Η, m), 7.41(2Η, τη), 7.51-7.52 ( 8Η, m), 7·77(4Η, π〇, 7·98(2Η, m), 8.12(2Η, m), 9·09(2Η, m&gt; 1047.29 1046.43 77 δ = 6.63(4Hf m)f 6.95 -6.97(8Η, m), 7.16-7.21(12Η, m), 7.41(2Hf m), 7.51-7.52(8Hf m)f 7.77(4H, m), 7.98(2H, τ〇, 8·12(2Η , m",9_09(2H, m) 929.20 928.29 78 δ = 6.59-6.63(8Hf m), 6.77(4Hf m)r 6.89-6.95(12H, m), 7.4K2H, m), 7.51-7.52 (8H, m), 7. 77(4H, m), 7.98(2Hf m), 8.12(2H, m), 9.09(2H, m) 897.07 896.34 79 δ = 6·63 (4H, m) , 6.73(8H, m), 6.95(4H / m) , 7.2K4H, m), 7.3(4H, m), 7.37-7.55(30H, m), 7.77(4H, m), 7.98(2H, ί\) , 8.12(2H, m), 9.09( 2Hf m) 1229.66 1228.46 80 δ = 1.3(8H, m), 1.45(8Η, m), 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(4H, m), 7·3(4Η, m), 7·41(2Η, m), 7.5 Bu 7·52(8Η, ro), 7.77(4H, 7·98(2Η, ir〇, 8·12(2Η, τι) , 9.09(2H, m) 1033.45 1032.43 81 δ = 2.71(8H, s), 6.63(4H, m), 6.73(8H, m) , 6.95(4H, m), 7·1 b 7.14(8H, m) , 7.21 &lt;4H, m), 7.3(4H, π〇, 7·41(2Η, m), 7.51-7.52(8H, m), 7.77(4H, m)f 7.98(2H, m), 8.12{ 2H, m), 9.09(2H, m) 1129.54 1128.43 82 δ = 2.88(8Η, m&gt;, 6.58~6.63(8H, m&gt;, 6.76(4H, m), 6.95(4H, τι), 7.02-7.04( 8Hr m) , 7.41{2Hf m) , 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 921.18 920.41 83 δ = 6.63 (8H, m), 6.81 (4H, m&gt;, 6.95~7 · 05( 12H, m), *7.25 (4H, m) , 7.41 (2H, , 7·5 b 7 · 52 (8H, m ), 7.77 HH, m) , 7.98 (2H, r 8.12 (2Hf m ), 9.09(2Hf m) 917.14 916.38 84 δ = 6.63(4H, m) , 6.69(4H, m), 6.87(4H, m), 6.95(4H, m), 7.16(4Η, m), 7.41-7.54 {18H, m), 7.77(4Hf m), 7.85(4H, m), 7·98(2Η, m), 8·12(2Η, m), 9·09(2Η, m) 1017.26 1016.41 85 δ = 1.53(12Η, m), 3.63 (4H, m), 5.99-6.05 (8H, m), 6.95(4H, 7.22~7_33(16H, m), 7·41(2Η, m), 7.51~7.52(8H , m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1077.40 1076.51 86 δ = 6.63(4Η, m), 6.95&lt;4H, m) , 7.14(4H, m), 7.32-7.41(10H, m), 7·51~7·52(8Η, m&gt;, 7·66(4Η, m), 7·77(4Η, m), 7.89( 4H, m), 7.98(2H, m), 8.12{2H, m)f 9.09(2Hf m) 1029.18 1028.36 87 δ = 6.63{8Hf m) , 6.81(2H, ro), 6.95(4H/ m) f 7.14 (2H, m), 7.2(4H, m) f 7.32-7.41(6H, m) , 7.51-7.52(8H, m) , 7,66(2H, m), 7.77(4H, m), 7.89(2H , m), 7·98(2Η, m), 8·12(2Η, m), 9.09(2H# m) 949.14 948.37 88 δ = 6.34(4Hr m), 6.63(4H, m) r 6.95(4H, m) , 7.41(2H, m) r 7.5-7.52(16H, m), 7.77~7.79(8H, m)f 7.98(6H, m), 8.12(2H, m), 9.09(2Hf m) 1093.45 1092.27 89 δ = 6·63 (8Η, ir〇, 6.81(2H, m&gt;, 6 95(4ΗΓ m), 7.2(4H, m), 7.4K2H, m), 7.51^7.53 (12H, m), 7.77(4Η, m), 7.98-8.01(4H, m), 8.12(2H, m) , 8.18{2H, m)f 9.09(2H, 983.25 982.32 41 95221 201204809 m) 90 δ = 6.63(4H, m), 6.95(4H, m), 7.39-7.41(10H, m), 7·51~7.52 (8H, m)r 7·74~7·77(12Η, m), 7·98(2Η, m), 8.12(2H, m), 9.09(2H, m) 1033.14 1032.34 91 δ = 1.35{36H, Si, 6.55 (8Hf m), 6.63 (4H, m), 6.95-7.0K12H, m), 7.41(2H, m), 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m) , 9.09(2H, m) 1093.53 1092.63 92 δ =* 0.25 (36H, s), 6.61 to 6.63U2H, m), 6.95(4H, m), 7.15{8Hf m), 7.4K2H, m), 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1157.83 1156.54 93 δ = 6.63 (4H , m), 6.73 (8H, m), 6.95 (4Hf in), 7.21 (8H, m), 7.37-7.55 (70H, m), 7.77(4Hf m) , 7.98(2H, m) , 8.12(2H, m), 9.09(2H, m) 1902.66 1900.73 94 δ = 6.61~6·63(12Η, 6.95-6.99(12H, m) , 7·41(2Η, m&gt;, 7.51-7.52(8H, m) , 7.77 (4H, m), 7.98(2H, m), 8.12(2H, τι), 9·09(2Η, m&gt; 941.06 940.34 95 δ = 6·56(8Η, m), 6.63( 4H, m), 6.95( 4H, m), 7.37~7_41&lt;l〇H, rr〇, 7:51~7·52(8Η, m), 7.77(4H, m), 7·98(2Η, m ), 8_12(2H, m), 9.09(2H, m) 1141.09 1140.33 96 δ = 6.63(4Η, m), 6.81(8H, m), 6.95(4H, m)f 7.39-7.41 (10H, m) , 7.51-7.52 (8H, m) , 7.77(4H, m) , 7.98(2H, m) , 8.12(2H, m), 9.09(2H, m) 969.14 968.36 97 δ = 3·83(12Η, s), 6.52(8H, 6·63(4Η, m), 6.74(8H, m), 6.95(4H,m), 7.41(2H,m),*7.51~7.52(8H,ir〇,7.77(4H, m) , 7·98(2Η, m), 8·12(2Η, m), 9.09(2H, m) 989.20 988.42 98 δ = 6.63(8H, m), 6.69{4Η, m) , 6.81(2H, m&gt; , 6.95(4Hf m), 7.2(4H, m), 7.41(4Hf m), 7.51-7.54 (20H, m), 7.77(4H, m), 7.98(2H, m)# 8.12(2Hr m), 9.09 (2H, m) 1021.29 1020.44 99 δ = 6.62-6.63 (8H, m) , 6.7(4Hf m), 6.95(4H, m) , 7.41(2H# m), 7.51-7.55(12H, m), 7.77( 4H, m), 7.98(2H, m), 8.07'8.12{6H# m), 9.09(2H, m) 873.05 872.36 100 δ = 6.63(4H, m), 6.95(4H, m), 7.27{4H, m) f 7.36*7.41(6Hf m), 7.51'7.52(8H, m) , 7.77{4H, m)f 7.98~8.12(12H, m), 9.09(2H, m) 873.05 872.36 101 δ = 6.63(8H , m), 6.7(2Hf m) , 6.81(4H, m) , 6 .95(4H, m), 7.2(8H, ro), 7·46(2Η, π〇, 7·58~7.59(6Η, m), 7'73&lt;2H, m), 7.86-7.92 (6H, m), 8(4H, m), 8.07(2H, m), 8.91(2Hf m) 971.19 970.40 102 δ = 6.63 (8H, m), 6.81 (2H, m), 6.95(4Hf m) , 7.2(4H / m) f 7.4K2H, m), 7.51-7.52 (8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 879.16 878.44 103 δ = 3.05(4H, m), 4.14(4H, m) , 6.55-6.6(6H, m), 6.72(2H, m), 6.95(4Η, m), 7·05~7.07(4H, ra) , 7·41(2Η, m), 7.51-7.52(8H, m), 7.8(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 768.98 768.35 42 95221 201204809 104 7.41(2«, m); 7'5lT; 2^H (47H«m&gt;, 7*〇5'7-〇7(4H, 8.12(2H, m)&gt; 9.〇9(2h, m;,,7-8&lt;4H&gt;mK7-98&lt;2^ 825,09 824.41 105 U('25h2 .41(2H, rn), 7.5~7.52(12H, m), 7.6~7.62(6H mi 7.93~ 7.98(6H, ra), 8.i2(2H, m), 9.09(2H. ' 764.95 764.32 106 7 &quot;;H1(4H,m),6-95&lt;^〇7TTr8H, m); 7.56(4H, m), 7.64(4H, m), 7.77~7.88(8H, m) 8 12(?H m), 8.93(2H, m), called, 8.12(2H, 869.10 858.38 107 7. -7.= = ^ 7.56~7.59(6H, &lt; 7.69(2H, m&gt;, l·— «-93(2«, m) 871.08 870.37 108 1 H, m)i ^.ϋ1!4Η, in), 6.96(2H, π〇&quot;T2iS» mi 7.45~7.49(4H, 7 ,7.2 (8H, m), 8 12f2H 〇' 7'69(2H^ m)^ 7-81~7.88(1〇h, m), 8.:12J2H, m)t 8-85(2H, m), 8.93 f2H. 873.05 872.36 109 7 41(2H Ί b.al(4H, and, 6.95(4Η,m), 7.2&lt;8H, &quot;»&gt;, I) 8 U2H V 7,56(12H,7 · 64(4^ 7.77(4H, &gt;f 8·1(2Η» 8.34(2H, m), 8.99(2Hr 1021.29 1020.44 110 δ — 6.63( 12HP m) c PlfiltT m\ r~~nT--- 7.4 K2H, m), 7.51~7.56{12H, m), 7.64(4H, m) 7 77,4« ...8: called 2H, m), 8·18(2η, ( q 7.77HH, 1021.29 1020-44 111 5;~7 8· ~ · Τ,7·64&lt;4Η,叫,7·77~7·88 Coffee (1), BU/ oi^(6H, m), 8.93(2H, m) 873.05 872.36 [Example 1 11] Fabrication of an OLED device using the organic electroluminescent compound of the present invention A germanium LED device is fabricated using the organic electroluminescent material of the present invention. First, a transparent electrode ιτο film (15 Ω / □) obtained from 0 LED (manufactured by Samsung Corning) was washed with trichloroethylene, acetone, ethanol, and distilled water in that order, and stored in isopropyl alcohol for use. Then, the [το substrate was assembled in a substrate holder of a vacuum vapor deposition apparatus, and 4, 4, 4,, _ gin (N, N-(2-naphthyl)-phenylamino) triphenylamine ( 2-TNATA) was placed in one of the cells of the vacuum vapor deposition apparatus, and the chamber was ventilated to a vacuum of 1 Torr to Torr. Next, a current is applied to the chamber to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm (nm) on the ΙΤ0 substrate. 0 95221 43 201204809 Next, Ν, Ν'-bis (α-naphthalene) a hydrazine, Ν'-diphenyl-4,4'-diamine (ΝΡΒ) is placed in another chamber of the vacuum vapor deposition apparatus, and an electric current is applied to the chamber to evaporate enthalpy, thereby forming the hole A hole transport layer having a thickness of 20 nm is formed on the injection layer. After the hole injection layer and the hole are formed, an electric field light-emitting layer is formed thereon in the following manner. The MA (Examples 1 to 3) was placed in a chamber of one of the vacuum vapor deposition apparatuses as a main body, and the compound of the present invention was placed in another chamber as a dopant. The two materials were vapor deposited at a rate of 100:3 to form an electric field luminescent layer having a thickness of 30 nm on the hole transport layer.

隨後，氣相沈積厚度為20nm之參（8-經基啥琳）紹（III) (Alq)作為電子傳輸層，及氣相沈積厚度為1至2nm之8-經基嗤琳链（lithium quinolate，Liq)作為電子注入層。 然後，使用另一真空氣相沉積裝置來形成厚度為150nm之 鋁（A1)陰極，以製造出0LED。 用於該0LED之各個化合物皆是已藉由在10_6 torr真 空昇華而純化者。 44 95221 201204809 尺（cd/m2)測量含有本發明之有 以1，000濁光/平方公 機電場發光化合物（實施你J J 發光效率。結果係顯示於表 至3所製造者）的OLED裝置之 2 ° 表2Subsequently, a vapor-deposited 20 nm-thick ginseng (8-by-base) (III) (Alq) was used as the electron transport layer, and a vapor-deposited thickness of 1 to 2 nm was obtained by a lithium quinolate. , Liq) as an electron injection layer. Then, another vacuum vapor deposition apparatus was used to form an aluminum (A1) cathode having a thickness of 150 nm to fabricate an OLED. Each of the compounds used in the OLED has been purified by sublimation at 10-6 torr. 44 95221 201204809 Ruler (cd/m2) Measure the OLED device containing the illuminating compound of the present invention with an emission field of 1,000 ton/mm square (implementing your JJ luminescence efficiency. The results are shown in Tables 3 to 3) 2 ° Table 2

由表2可知’本發明之有機電場光化合物係提供深藍 色有CIE 之程度之藍色為在有機電場發光顯 不器中實現該顏色接近NTSC標準所需者時，本發明之有機 電場發光化合物係㈣。由於諸生物具有高玻璃轉移溫 度，因此可得到較高的熱安定性。如上述，使用本發明之 有機電場發光化合物係作為具有高純度之發射藍光材料使 用。 【圖式簡單說明】 無。 【主要元件符號說明】 無0 95221 45It can be seen from Table 2 that the organic electric field light-emitting compound of the present invention provides a dark blue color to the extent of CIE, and is an organic electroluminescent compound of the present invention when it is required to achieve the color close to the NTSC standard in an organic electric field luminescence display. Department (four). Since the organisms have a high glass transition temperature, higher thermal stability can be obtained. As described above, the organic electroluminescent compound of the present invention is used as a blue-emitting material having high purity. [Simple description of the diagram] None. [Main component symbol description] None 0 95221 45

Claims (1)

201204809 七、申請專利範圍： 1. 一種化學式1表示之有機電場發光化合物： [化學式1]201204809 VII. Patent application scope: 1. An organic electric field luminescent compound represented by Chemical Formula 1: [Chemical Formula 1] 其中， Ri、R4、R?及Rid係獨立表示氫、（C1-C30)烧基、 (C3-C30)環烷基、5至7員雜環烷基、（C6-C30)芳基、 (C2-C30)雜芳基、-NReRf[其中，Re及Rf係獨立表示 (CU-C30)烷基或（C6-C30)芳基]、RaRbRcSi-[其中，Ra、 Rb及Re係獨立表示（C1-C30)烧基或（C6-C30)芳基]、RdY-[其中，Y表示0或呂，且Rd表示（C1-C30)烧基或（C6-C30) 芳基]或但排除R,、R4、R7及R,。中之兩 者為氫之情況； R2、R3、R5、R6、R8及R9係獨立表示氩、（C卜C30) 烷基、（C3-C30)環烷基、5至7員雜環烷基、（C6-C30) 芳基、（C2_C3〇)雜芳基、-NReRf[其中，Re&amp; Rf係獨立 表示（C1-C30)烷基或（C6-C30)芳基]、RaRbRcSi-[其中， Ra、Rb及Re係獨立表示（C1-C30)烷基或（C6-C30)芳基] 或RdY-[其中，Y表示0或S，且Rd表示（C1-C30)烷基 或（C6-C30)芳基]; L!表示單鍵、（C6-C30)伸芳基或（C2-C30)伸雜芳 1 95221 201204809 V 基ϊWherein, Ri, R4, R? and Rid independently represent hydrogen, (C1-C30) alkyl, (C3-C30) cycloalkyl, 5 to 7 membered heterocycloalkyl, (C6-C30) aryl, ( C2-C30)heteroaryl, -NReRf [wherein Re and Rf independently represent (CU-C30)alkyl or (C6-C30)aryl], RaRbRcSi-[wherein Ra, Rb and Re are independently represented ( C1-C30) alkyl or (C6-C30) aryl], RdY-[wherein Y represents 0 or len, and Rd represents (C1-C30)alkyl or (C6-C30) aryl] or excludes R ,, R4, R7 and R,. The two are hydrogen; R2, R3, R5, R6, R8 and R9 independently represent argon, (C-C30) alkyl, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl (C6-C30) aryl, (C2_C3〇)heteroaryl, -NReRf [wherein Re&amp; Rf is independently represented by (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi-[where Ra, Rb and Re independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY-[wherein Y represents 0 or S, and Rd represents (C1-C30)alkyl or (C6- C30) aryl]; L! represents a single bond, (C6-C30) extended aryl or (C2-C30) extended heteroaryl 1 95221 201204809 V ϊ L:表示（C6-C30)伸芳基、（C2-C30)伸雜芳基或 心及Ru係獨立表示（C3-C30)環烷基、5至7員雜L: represents (C6-C30) aryl, (C2-C30) heteroaryl or heart and Ru is independently represented by (C3-C30) cycloalkyl, 5 to 7 member 環烷基、（C6-C30)芳基、（C2-C30)雜芳基或 ，或者Rii及Rn可經由具有或不具有稠合環之 伸烷基或（C3-C30)伸烯基相鏈結以形成稠合環，且該伸 烧基的碳原子可經NR2〖、〇、或s取代，其中心表示氣、 (C1-C30)烷基、i ((n-C30)烷基、（C1-C30)烷氧基、卜 嗎啉基、N-硫代嗎啉基、N-哌啶基、5至7員雜環烷美、 (C3-C30)環烷基、i 素、氰基、（C6_C3〇)芳基、（C2_C3〇) 雜芳基或RaRbRcS i -[其中，P、Rb及RC係獨立表示（c i 3 烷基或（C6-C30)芳基]; Z2 係獨立表示-(CR3lR32)m---(R3,)C=C(r32)_ n ~N(R33)_、_S_、~0_、-Se-或-Si(R34)(R35); 心至R35係獨立表示氫、（C1-C30)烷基、（C3_C3〇) 環烷基、5至Y員雜環烷基、（C6_C3〇)芳基、㈡ 、Rb 及 Rc 或者R31 雜芳基、一NReRf[其中’ Re及Rf係獨立表示（Cl-C30)r 基或（C6-C30)芳基]、或 RaRbRcSi_[其中，Ra、 二 係獨立表示（C1-C30)烷基或（C6_C3〇)芳基] 、、 /々孤」、或者r31 至R35可各自經由具有或不具有稠合環之（C3-C30)伸尸 基或（C3-C3G)㈣基鏈結至相鄰取代基以形成脂環= 95221 2 201204809 環、或單環或多環之芳香環； Rl至R!。及R”至R35之該烷基、環烷基、雜環烷基、 芳基或雜芳基；Li及L2之該伸芳基或伸雜芳基；|^及 Rl2之該環烷基、雜環烷基、芳基或雜芳基；以及經由 將R&quot;及心鏈結所形成之該稠合環，係可進一步經一個 或多個選自氘、（Cl-C30)烷基、（C6-C30)芳基、（C1 _C3〇) 烷氧基、氰基、（C1-C30)烷基矽烷基、（C6_C3〇)芳基矽 烷基、^(Cl-C30)烷基、（C3-C30)雜芳基、（C3 土 環烷基、硝基及經基之取代基所取代； ㈧ 該雜環貌基或雜芳基可含有一個或多個選自Cycloalkyl, (C6-C30) aryl, (C2-C30)heteroaryl or, or Rii and Rn via an alkyl or (C3-C30) extending alkenyl chain with or without a fused ring To form a fused ring, and the carbon atom of the alkyl group can be substituted by NR2, 〇, or s, the center of which represents gas, (C1-C30) alkyl, i ((n-C30) alkyl, ( C1-C30) alkoxy, bumorpholinyl, N-thiomorpholinyl, N-piperidinyl, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, i-, cyano , (C6_C3〇) aryl, (C2_C3〇)heteroaryl or RaRbRcS i - [wherein P, Rb and RC are independently represented (ci 3 alkyl or (C6-C30) aryl]; Z2 is independently represented - (CR3lR32)m---(R3,)C=C(r32)_ n ~N(R33)_, _S_,~0_, -Se- or -Si(R34)(R35); Heart to R35 are independent representation Hydrogen, (C1-C30)alkyl, (C3_C3〇)cycloalkyl, 5- to Y-membered heterocycloalkyl, (C6_C3〇)aryl, (ii), Rb and Rc or R31 heteroaryl, a NReRf [where ' Re and Rf are independently represented by (Cl-C30)r group or (C6-C30)aryl group, or RaRbRcSi_[wherein, Ra, the second system independently represents (C1-C30) alkyl group or (C6_C3〇) aryl group], , /々孤" Or r31 to R35 may each form an alicyclic ring via a (C3-C30) cadaveric group or a (C3-C3G)(tetra)-based chain with or without a fused ring to form an alicyclic ring = 95221 2 201204809 ring, or single a cyclic or polycyclic aromatic ring; R1 to R! and R' to R35 of the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; Li and L2 of the aryl or hetero The cycloalkyl, heterocycloalkyl, aryl or heteroaryl group of the aryl group; and R1; and the fused ring formed by the R&quot; and the cardiac linkage may further pass through one or more Selected from hydrazine, (Cl-C30) alkyl, (C6-C30) aryl, (C1 _C3 fluorene) alkoxy, cyano, (C1-C30) alkyl fluorenyl, (C6_C3 fluorene) aryl decyl , (Cl-C30) alkyl, (C3-C30)heteroaryl, (C3 ring alkyl, nitro and substituted by a substituent; (VIII) the heterocyclic or heteroaryl group may contain a Or multiple selected from 係化學式2或3所示者： [化學式2]Those shown in Chemical Formula 2 or 3: [Chemical Formula 2] [化學式3] 95221 3 201204809[Chemical Formula 3] 95221 3 201204809 其中， Lu及L12係獨立表示（C6-C30)伸芳基、（C2-C30)伸 雜芳基或Wherein, Lu and L12 are independently represented by (C6-C30) aryl, (C2-C30) heteroaryl or Lu及Lu係獨立表示（C6-C30)伸芳基或（C2-C30)伸 雜芳基； R2、R3、Rs、R6、R8 及 Rg 係獨立表示氫、（C1-C30) 烷基、（C3-C30)環烷基、5至7員雜環烷基、（C6-C30) 芳基或（C2-C30)雜芳基； R41至R44係獨立表示（C3-C30)環燒基、5至7員雜Lu and Lu are independently represented by (C6-C30) aryl or (C2-C30) heteroaryl; R2, R3, Rs, R6, R8 and Rg are independently represented by hydrogen, (C1-C30) alkyl, ( C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-C30) aryl or (C2-C30)heteroaryl; R41 to R44 are independently represented by (C3-C30)cycloalkyl, 5 To 7 members 環烷基、（C6-C30)芳基、（C2-C30)雜芳基或 ’或者經由具有或不具料合環之（C3_C3〇) 伸烧基或（G3-G3G)料基相鏈結以形成稠合環，且該伸 燒基的碳原子可經NR21、〇、或S取代，其中&amp;表示氣、 (a-c3〇)絲、i (c卜⑽）絲、.⑽烧氧基、n— 嗎啉基、N-硫代嗎啉基、N—哌啶基、5至7員雜 (C3-C30)環烧基、齒素、氰基、（C6_C3{))芳基) 雜芳基或RaRbResi-[其中，RUr係獨立表示（c卜⑽ 95221 4 201204809 烷基或（C6-C30)芳基]; Zl及Z2係獨立表示―⑽心)》-、-(R31)OC(R32)、、 -N(R33)- &gt; -s- ' -o Se-或〜Si(R34)(R35); 心至R35係獨立表示氫、（cl_c3〇)烷基、 環烧基、5至7員雜環烧基、（C6_C3〇)芳基、⑽ 雜芳基、-Nim其中，Re*Ri係獨立表示（… ） 基或（C6-C30)芳基]、或 RaRbRCsi 一[其中，y^ 及二 係獨立表不（C1-C30)烷基或（C6_C3〇)芳基];或者只 至r35可各自經由具有或不具有稠合環之（C3_C3 基或（C3-C3G)伸稀基鍵結至相鄰取代基以形成 : 環、或單環或多環之芳香環； &lt; ' 1^、^7及Rl。係獨立表示氫、（cl_C3〇)烷基 (C3-C30)雜基、5至7員雜環絲、⑽_⑽）芳基 (C2-⑽雜芳基、-Nm其+ n Rf係獨立^示 (C1-C30)烧基或（C6-C30)芳基]、RaRbRcgi [其中，P、、 Rb及Re係獨立表示（C1-C30)烷基或（C6_C3〇)芳基]戋 RdY-[其中，Y表示0或S，且Rd表示（cl_C3〇)烷基^ (C6-C30)芳基]; 一 R!至Ri。之該烷基、環烷基、雜環烷基、芳基或雜 芳基，以及Lu、Li2、bi及L22之該伸芳基或伸雜芳基可 進一步經一個或多個選自氘、（C1-C30)烧基、（C6-C30) 芳基、（C1-C30)烷氧基、氰基、（C1-C30)烷基矽烷基、 (C6-C30)芳基矽烷基、齒（C1-C30)烷基、（C3-C30)雜芳 基、（C3-C30)環烷基、硝基及羥基之取代基所取代；以 5 95221 201204809 ， 及 m表示整數0、1或2。 3.如申請專利範圍第2項所述之有機電場發光化合物，其 中，Lu及Lu係獨立表示伸苯基、伸萘基、伸聯苯基、 伸菲基、伸吼哄基、伸三哄基、伸喹啉基、伸啡啉基、 伸噻吩基、伸呋喃基、伸硒苯基、伸噻二唑基、伸卩萼二 吐基、伸ί西二唑基或伸喹曙琳基’或者為選自下列結構 之二價基團：Cycloalkyl, (C6-C30) aryl, (C2-C30)heteroaryl or 'either via a (C3_C3〇) extender or (G3-G3G) base phase chain with or without a ring of Forming a fused ring, and the carbon atom of the extended alkyl group may be substituted by NR21, hydrazine, or S, wherein & represents gas, (a-c3〇) wire, i (cb (10)) wire, (10) alkoxy group , n-morpholinyl, N-thiomorpholinyl, N-piperidinyl, 5 to 7 membered hetero (C3-C30) cycloalkyl, dentate, cyano, (C6_C3{)) aryl) Aryl or RaRbResi-[wherein, RUr is independently represented (c) (10) 95221 4 201204809 alkyl or (C6-C30) aryl]; Z1 and Z2 independently represent "(10) heart)"-, -(R31)OC ( R32), -N(R33)- &gt; -s- '-o Se- or ~Si(R34)(R35); Heart to R35 are independently hydrogen, (cl_c3〇)alkyl, cycloalkyl, 5 Up to 7 membered heterocycloalkyl, (C6_C3〇) aryl, (10) heteroaryl, -Nim wherein Re*Ri is independently represented by (...) group or (C6-C30) aryl], or RaRbRCsi-[where y^ and the second series independently represent (C1-C30)alkyl or (C6_C3〇)aryl]; or only r35 may be via each with or without a fused ring (C3_C3) The base or (C3-C3G) stretching group is bonded to an adjacent substituent to form: a ring, or a monocyclic or polycyclic aromatic ring; &lt; '1^, ^7 and Rl. independently represent hydrogen, (cl_C3) 〇) alkyl (C3-C30) hetero, 5- to 7-membered heterocyclic, (10)-(10)) aryl (C2-(10) heteroaryl, -Nm, + n Rf, independently (C1-C30) alkyl or (C6-C30) aryl], RaRbRcgi [wherein P, Rb and Re independently represent (C1-C30) alkyl or (C6_C3〇) aryl] 戋 RdY- [where Y represents 0 or S, and Rd represents (cl_C3〇)alkyl^(C6-C30)aryl]; a R! to Ri. of the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl, and Lu, Li2 The aryl or heteroaryl group of bi and L22 may be further selected from one or more selected from the group consisting of hydrazine, (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkoxy, cyanide , (C1-C30)alkyldecylalkyl, (C6-C30)aryldecylalkyl, dentate (C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitrate Substituted by a substituent of a hydroxy group; 5, 025, 201204809, and m represents an integer of 0, 1 or 2. 3. Organic field luminescence as described in claim 2 a compound in which Lu and Lu independently represent a phenylene group, a naphthyl group, a phenylene group, a phenanthrenyl group, a fluorenyl group, a decyl group, a quinolinyl group, a phenanthroline group, and a thienyl group. , a furanyl group, a selenophenylene group, a thiadiazole group, a stilbene group, a oxadiazolidine group or a quinoxaline group or a divalent group selected from the following structures: Rm至R35係獨立表示氫、曱基、乙基、正丙基、異 丙基、正丁基、異丁基、第三丁基、戊基、戊烷基、己 基、庚基、辛基、壬基、癸基、三氟曱基、苯基、萘基、 聯笨基、苐基或菲基，或者RS1至R35可各自經由具有或 不具有稠合環之（C3-C30)伸烷基或（C3_C3〇)伸烯.基鏈 結至相鄰取代基以形成脂環族環、或單環或多環之芳香 環； Ln及L22係獨立表示伸笨基、伸萘基、伸苜美 第基、伸菲基、伸聯苯基、伸三苯基、伸丙 伸蒯基、伸芘基、伸茈基、伸啦啶基、伸呋喃基 '伸噻 吩基、伸砸苯基、伸吼畊基、伸嗒畊基、伸喹啉基或 喹噚啉基； 95221 6 201204809 R2、R3' r5、r6、r8及r9係獨立表示氫、甲基、乙 基、正丙基、異丙基、正丁基、異丁基、第三丁基、戊 基、戊烷基、己基、庚基、辛基、壬基、癸基、三氟甲 基、環丙基、環丁基、環戊基、環己基、環庚基、環辛 基、笨基、萘基、聯笨基、第基、菲基、吼啶基、呋喃 基、噻吩基、喹啉基、異喹啉基、啡啉基、咔唑基、三 哄基或啦。定基； 心至R44係獨立表示環丙基、環丁基、環戊基、環 己基、環庚基、環辛基、苯基、萘基、聯笨基、茚基、 苐基、苯并苐基、螺二苐基、蒽基、芘基、菲基、聯伸 二苯基、丙二烯合第基、吡啶基、呋喃基、噻吩基、喹 啉基、異喹啉基、啡啉基、咔唑基、苯并呋喃基、苯并 噻吩基、苯并噻唑基、苯并噚唑基、三哄基、嘧啶基或Rm to R35 independently represent hydrogen, mercapto, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, pentyl, hexyl, heptyl, octyl, Anthracenyl, fluorenyl, trifluoromethyl, phenyl, naphthyl, phenyl, fluorenyl or phenanthryl, or RS1 to R35, each via a (C3-C30) alkyl group with or without a fused ring Or (C3_C3〇) an extended alkyl group to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; Ln and L22 independently represent a stupid base, a naphthyl group, and a beautiful The first group, the phenanthrene group, the extended biphenyl group, the exotriphenyl group, the extensor-extended thiol group, the exfoliating group, the exfoliating group, the exo-pyridine group, the furanyl group, the thiophene group, the phenyl group, the hydrazine Ploughing, stretching, quinolinyl or quinoxalinyl; 95221 6 201204809 R2, R3' r5, r6, r8 and r9 are independently hydrogen, methyl, ethyl, n-propyl, isopropyl , n-butyl, isobutyl, tert-butyl, pentyl, pentyl, hexyl, heptyl, octyl, decyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl Base, cyclohexyl, ring Base, cyclooctyl, stupid, naphthyl, phenyl, decyl, phenanthryl, acridinyl, furyl, thienyl, quinolyl, isoquinolinyl, morpholinyl, oxazolyl, tri哄基或啦. The base to R44 is independently represented by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, phenyl, fluorenyl, fluorenyl, benzopyrene , spirobifluorenyl, fluorenyl, fluorenyl, phenanthryl, co-diphenyl, propadienyl, pyridyl, furyl, thienyl, quinolinyl, isoquinolinyl, morpholinyl, Carbazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzoxazolyl, tridecyl, pyrimidinyl or Ri、R4、R?及Rio係獨立表示氫、甲基、乙基、正丙 基、異丙基、正丁基、異丁基、第三丁基、戊基、戊烷 基、己基、庚基、辛基、壬基、癸基、三氟甲基、環丙 基、環丁基、環戊基、環己基、環庚基、環辛基、苯基、 萘基、聯苯基、第基、菲基、吼啶基、呋喃基、噻吩基、 喹啉基、異喹啉基、啡啉基、咔唑基、三畊基或嘧啶基； 以及 Ln、Li2、1^及L22、匕至R1Q及r41至R44可進一步經 95221 7 201204809 一個或多個選自氘、（C1-C30)烷基、（C6-C30)芳基、 (C1-C3G)錄基、氰基、（e卜咖德基⑦絲、（C6_C3〇) 方基矽烷基、li (C1-C30)烷基、（C3_C3〇)雜芳基、 (C3-C3G)^烷基、硝基及羥基之取代基所取代。 如中，專利第3項所述之有機電場發光化合物，盆 〇41、 R43n 八 tb , .N-* τι -Ν- * R42 及R4/ 係獨立選自下列結構：Ri, R4, R? and Rio are independently represented by hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, pentyl, hexyl, g. Base, octyl, decyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, , phenanthryl, acridinyl, furyl, thienyl, quinolyl, isoquinolyl, morpholinyl, oxazolyl, tri-n- or pyrimidinyl; and Ln, Li2, 1^ and L22, 匕To R1Q and r41 to R44 may be further subjected to 95221 7 201204809 one or more selected from the group consisting of hydrazine, (C1-C30) alkyl, (C6-C30) aryl, (C1-C3G), cyano, (e) Substituted by a substituent of cadmium, (C6_C3〇), arylalkyl, li(C1-C30)alkyl, (C3_C3〇)heteroaryl, (C3-C3G)^alkyl, nitro and hydroxy For example, the organic electroluminescent compound described in Patent No. 3, Potassium 41, R43n 八tb, .N-* τι -Ν-* R42 and R4/ are independently selected from the following structures: 5.5. &amp;至R35係獨立表示（C1_C30)烷基或（C6_C3〇)芳 基，或者R3m可各自經由具有或不具有稠合環之 (C3-C30)伸絲或⑽韻）伸烯基鏈結至相鄰取代基 以形成脂環族環、或單環或多環之芳香環。 土 一種有機電場發光裝置，係包括如ΐ請專利範圍第！ 至4項中任-項所述之有機電場發光化合物。 如甲晴專利範圍第 w丨4〜力饵电嘮發光裝置，其 〇括第-電極，第二電極；以及—層或多層插置於今 二電極與該第二電極間之有機層；其t，該有機声包' 一種或多種如申請專利範圍第1至4射任1所述· 有機電場發光化合物，以及—種或多種選自化學式 或5表示之化合物之主體： 工 95221 8 201204809 [化學式4] (Ari01)a-Ll01_(Ari02)b [化學式5] (Ari03)c-Ll02_( Ari04)d 其中 Lm表示（C6-C30)伸芳基或（C4-C30)伸雜芳基； Ll02表示伸蒽基； Arm至An〇4係獨立表示氫、氘、（cl_C3〇)烷基、 (C1-C30)烷氧基、函素、（C4_C3〇)雜芳基、（C5_C3〇) 環烷基或（C6-C30)芳基，且紅1()1至An〇4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 群組之取代基所取代：具有或不具有一個或多個選自具 有或不具有_素取代基之（C1-C30)烷基、（a-C30)烷氧 基、（C3-C30)環烷基、函素、氰基、三（cl_C3〇)烷基矽 烷基、二（C1-C30)烷基（C6-C30)芳基矽烷基及三 (C6-C30)芳基矽基所組成群組之取代基之（C6 C3〇)芳 基或（C4-C30)雜芳基；具有或不具有齒素取代基之 (C卜C30)烧基；（C1-C30)燒氧基；（C3_C3〇)環烧基；自 素、氰基、二（C1-C30)烷基矽烷基、二（cl_C3〇)烷基 (C6-C30)芳基矽烷基及三（C6_C3〇)芳基矽烷基 ;以及 a、b、c及d係獨立表示0至4之整數。 7·如申請專利範圍第6項所述之有機電場發光裝置，其 中:該有機層進一步包括一種或多種選自芳基胺化合物 及苯乙婦基芳基胺化合物所組成群組之胺化合物。 95221 9 201204809 8. 如申請專利範圍第6項所述之有機電場發光裝置，其 中，該有機層進一步包括一種或多種選自下列組成群組 之金屬：第1族之有機金屬、第2族、第4周期與第5 周期之過渡金屬、鑭系金屬及d-過渡元素。 9. 如申請專利範圍第6項所述之有機電場發光裝置，其 中，該有機層包括電場發光層及電荷產生層。 10. 如申請專利範圍第6項所述之有機電場發光裝置，其為 發射白光之有機電場發光裝置，其中，該有機層進一步 包括一層或多層發射藍光、紅光或綠光之有機電場發光 層。 10 95221 201204809 四、指定代表圖： (一) 本案指定代表圖為：本案無圖式。 (二) 本代表圖之元件符號簡單說明：無。 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1]&amp; R35 is independently represented by (C1_C30)alkyl or (C6_C3〇)aryl, or R3m may each independently extend to the alkenyl chain via (C3-C30) or (10) rhyme with or without a fused ring Adjacent substituents form an alicyclic ring, or a monocyclic or polycyclic aromatic ring. Earth An organic electric field illuminating device, including the scope of patents such as ΐ! The organic electroluminescent compound of any one of the above-mentioned items. For example, the patent scope of the patent is in the range of w丨4~force bait electroluminescent device, which comprises a first electrode, a second electrode, and a layer or layers interposed between the organic electrodes of the present electrode and the second electrode; , the organic sound package 'one or more as claimed in the patent scopes 1 to 4 of the first embodiment of the organic electroluminescent compound, and one or more selected from the chemical formula or the compound represented by 5: 95221 8 201204809 [Chemical formula 4] (Ari01)a-Ll01_(Ari02)b [Chemical Formula 5] (Ari03)c-Ll02_(Ari04)d wherein Lm represents (C6-C30) extended aryl or (C4-C30) heteroaryl; Ll02 represents The Arm to An〇4 series independently represents hydrogen, hydrazine, (cl_C3〇)alkyl, (C1-C30) alkoxy, a functional, (C4_C3〇)heteroaryl, (C5_C3〇)cycloalkyl Or (C6-C30) aryl, and the cycloalkyl, aryl or heteroaryl group of red 1 () 1 to An 〇 4 may be further substituted by one or more substituents selected from the group consisting of : with or without one or more (C1-C30) alkyl groups, (a-C30) alkoxy groups, (C3-C30) cycloalkyl groups, and functional groups selected from the group consisting of having or without a substituent. a substituent consisting of a group consisting of a tris(cl_C3〇)alkyldecanealkyl group, a di(C1-C30)alkyl group (C6-C30)aryldecylalkyl group and a tris(C6-C30)arylfluorenyl group (C6) C3〇) aryl or (C4-C30)heteroaryl; (CBuC30)alkyl having or without a dentate substituent; (C1-C30) alkoxy; (C3_C3〇)cycloalkyl; a cyano group, a cyano group, a bis(C1-C30)alkyl fluorenyl group, a bis(cl_C3 fluorene)alkyl group (C6-C30) aryl decyl group and a tris(C6_C3 fluorene) aryl decyl group; and a, b, c and d is an integer representing 0 to 4 independently. 7. The organic electroluminescent device of claim 6, wherein the organic layer further comprises one or more amine compounds selected from the group consisting of arylamine compounds and phenethyl arylamine compounds. The organic electroluminescent device of claim 6, wherein the organic layer further comprises one or more metals selected from the group consisting of: organometallics of Group 1, Group 2, Transition metals, lanthanide metals and d-transition elements in the 4th and 5th cycles. 9. The organic electroluminescent device of claim 6, wherein the organic layer comprises an electric field luminescent layer and a charge generating layer. 10. The organic electric field light-emitting device according to claim 6, wherein the organic light-emitting device emits white light, wherein the organic layer further comprises one or more organic light-emitting layers emitting blue, red or green light. . 10 95221 201204809 IV. Designated representative map: (1) The representative representative of the case is: There is no schema in this case. (2) A brief description of the symbol of the representative figure: None. 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] R4 Ri 尸1〇 R2 &gt;=( I 2 95221R4 Ri corpse 1〇 R2 &gt;=( I 2 95221
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