TW201114880A - 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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TW201114880A
TW201114880A TW099120052A TW99120052A TW201114880A TW 201114880 A TW201114880 A TW 201114880A TW 099120052 A TW099120052 A TW 099120052A TW 99120052 A TW99120052 A TW 99120052A TW 201114880 A TW201114880 A TW 201114880A
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group
aryl
alkyl
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TW099120052A
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TWI461509B (en
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Chi-Sik Kim
Young-Jun Cho
Hyuck-Joo Kwon
Bong-Ok Kim
Sung-Min Kim
Seung-Soo Yoon
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Dow Advanced Display Material Ltd
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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Abstract

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

Description

201114880 '六、發明說明： ，【發明所属之技術領域】 .本發明係關於一種新穎有機電場發光化合物及包含 該化合物之有機電場發光裝置。根據本發明之有機電場發 光化合物係如化學式（1)所示：201114880 'VI. Description of the invention: [Technical field to which the invention pertains] The present invention relates to a novel organic electroluminescent compound and an organic electric field illuminating device comprising the same. The organic electric field emitting compound according to the present invention is as shown in the chemical formula (1):

(1) 【先前技術】 在眾多顯示裝置之中，電場發光裝置 (electroluminescent, EL)作為自體發光裝置的優點在於 它們提供了寬廣的視角、優越的對比與高回應速率。1987 年時，Eastman Kodak首先開發出一種有機EL裝置，其係 使用低分子量芳香族二胺與鋁錯化物作為形成電場發光層 之物質[办/?人户紅又Zeii· 51，913，1987]。(1) [Prior Art] Among a plurality of display devices, an electroluminescent device (EL) as an autoluminescent device has an advantage in that it provides a wide viewing angle, superior contrast, and high response rate. In 1987, Eastman Kodak first developed an organic EL device using low molecular weight aromatic diamines and aluminum complexes as materials for forming an electric field luminescent layer. [Office/? .

在有機EL裝置中，當施加電荷至有機層（形成於電子 注入電極（陰極）與電洞注入電極（陽極）之間）時，電子與電 洞會配成對，並在電子-電洞對消耗後發射出光。有機EL 裝置的優點在於：其可形成於撓性透明基材上（例如塑 膠）；相較於電漿顯示器面板或無機EL顯示器，其用相對 低的電壓（10或更低）即可操作；消耗較低的功率；以及提 供優質的顏色。此外，因能呈現綠、藍及紅色，有機EL 3 94915 201114880 裝置受矚目成為下一代、全色彩顯示裝置。 ^在有機EL裝置中，決定其效能（包括發光效率與操作 壽命）的最重要因素為電場發光材料。電場發光材料的一些 要件包括於固態之南電場發光量子產率（叫抓_、 向電子及電洞遷移率、真空沉積期間的高分解抗性、形成 均勻薄膜的能力以及穩定性。 一般而言，有機EL·裝置通常具有陽極/電洞注入層 (HIL)/電洞傳輸層（HTL)/發光材料層（EML)/電子傳輸層 (ETL)/電子主入層（eil)/陰極之組構。有機電場發光裝置 發射藍、綠或紅光者，其可依據如何形成發光材料層而製 造。 在功犯性方面，電場發光材料可切分為主體材料與摻 雜劑材料。一般而言，已知電場發光層藉由摻雜摻雜劑於 主體中而製造者能提供優越的EL特性。近來，開發具高效 率與長操作壽命之有機EL正成為迫在眉急的要務。尤其 是，考慮到中至大尺寸（0LED)面板需要之EL效能程度，開 發明顯優於現存電場發光材料之材料有迫切的需求。 就藍光電場發光材料而言，許多材料已接著Idemitsu Kosan的DPVBi之後商品化了。除了 Idemitsu Kosan的藍 光材料系統以外，Kodak的二萘基蒽 (dinaphthylanthracene)及四（第三丁基）花 (tetra(t-butyl)perylene)已為眾知，但仍需要進一步的 研究與開發。迄今為止，已知Idemitsu Kosan的二苯乙烯 化合物具有最佳的發光效率。其呈現6流明/瓦（lm/w)的功 4 94915 201114880 '' ，〇〇小時或更長的操作壽命。然而，其天空藍 ^lue)顏色並不適合於全彩色顯示器。一般而言，如 二琢發光波長稍往較長波長偏移，藍光電場發光在發光 ，率方面就變得有利。但是，如此並不適用於高品質顯示 益’因為無法達到純藍的顏色。因此，改善色純度（c〇l〇rIn an organic EL device, when charges are applied to an organic layer (formed between an electron injecting electrode (cathode) and a hole injecting electrode (anode)), electrons and holes are paired and in an electron-hole pair After the consumption, the light is emitted. An advantage of the organic EL device is that it can be formed on a flexible transparent substrate (such as plastic); it can be operated with a relatively low voltage (10 or lower) compared to a plasma display panel or an inorganic EL display; Consumes lower power; and provides superior color. In addition, the organic EL 3 94915 201114880 device has attracted attention as a next-generation, full-color display device due to its ability to display green, blue and red. ^ In an organic EL device, the most important factor determining its performance (including luminous efficiency and operational lifetime) is an electric field luminescent material. Some elements of the electric field luminescent material include the quantum yield of the south electric field luminescence in the solid state (called scratching, electron and hole mobility, high decomposition resistance during vacuum deposition, ability to form a uniform film, and stability. Organic EL devices typically have an anode/hole injection layer (HIL)/hole transport layer (HTL)/luminescent material layer (EML)/electron transport layer (ETL)/electron master entry layer (eil)/cathode group The organic electric field illuminating device emits blue, green or red light, which can be manufactured according to how to form a luminescent material layer. In terms of dysfunction, the electric field luminescent material can be divided into a host material and a dopant material. It is known that an electric field luminescent layer can provide superior EL characteristics by doping a dopant into a host. Recently, developing an organic EL with high efficiency and long operating life is becoming an urgent task. Considering the degree of EL performance required for medium to large size (0LED) panels, there is an urgent need to develop materials that are significantly better than existing electroluminescent materials. In the case of blue light field luminescent materials, many materials have followed Idemitsu. Kosan's DPVBi was later commercialized. In addition to Idemitsu Kosan's blue light material system, Kodak's dinaphthylanthracene and tetra(t-butyl)perylene are well known, but Further research and development is still needed. To date, Idemitsu Kosan's stilbene compound has been known to have the best luminous efficiency. It exhibits 6 lumens per watt (lm/w) of work 4 94915 201114880 '', 〇〇 hours or Longer operating life. However, its sky blue ^lue) color is not suitable for full color displays. In general, if the wavelength of the second illuminating light is shifted by a relatively long wavelength, the blue light electric field illuminates in terms of luminescence, and the rate becomes favorable. However, this does not apply to high-quality display benefits because it is impossible to achieve a pure blue color. Therefore, improving color purity (c〇l〇r

Purity)、效率以及熱敎性的研究及開發有著高度 求。 為了提供具高效率與長壽命的主體材料，已有各種具 不同骨幹結構的EL化合物被揭露，包括二螺_苐_蒽 (dispiro-fluorene_anthracene)(TBSA)、三一螺苐 (ter-spirofluorene)(TSF)、雙聯伸三苯（bitriphenylene) (BTP)等。然而，它們都無法在色純度或發光效率方面提供 令人滿意的結果。Purity, efficiency and enthusiasm for research and development are highly desirable. In order to provide a host material having high efficiency and long life, various EL compounds having different backbone structures have been disclosed, including dispiro-fluorene_anthracene (TBSA) and ter-spirofluorene. (TSF), double-stranded phenylene (BTP), etc. However, none of them can provide satisfactory results in terms of color purity or luminous efficiency.

TBSA 係由 Gyeongsang University 及 Samsung SDITBSA is from Gyeongsang University and Samsung SDI

[Kwon，S. K. et al.，Advanced Materials, 2001，13, 1690 ; 曰本專利早期公開案JP 2002121547]所發表者，其於7. 7 伏特（V)下表現出3燭光/安培（cd/A)之發光效率，以及相 對較好的色坐標（color corrdinate)(〇. 15, 〇. 11)，但是其 為單層之材料，且不適合商業用途。 TSF 係由國立臺灣大學（Wu，C. C. et a 1.，Advanced Materials，2004, 16, 61 ;美國專利公開案 US 2005040392) 所發表者’其表現出相對較好的外部量子效率（5.3%)，但 對實際應用仍不足。此外，BTP係由國立臺灣清華大學 (Cheng，C. -H. etal.，Advanced 5 94915 201114880[Kwon, SK et al., Advanced Materials, 2001, 13, 1690; pp. JP 2002121547], which exhibits 3 candelas/amperes (cd/A) at 7. 7 volts (V). The luminous efficiency, as well as relatively good color corrminate (〇. 15, 〇. 11), but it is a single layer of material and is not suitable for commercial use. The TSF is published by National Taiwan University (Wu, CC et al 1., Advanced Materials, 2004, 16, 61; US Patent Publication US 2005040392), which exhibits relatively good external quantum efficiency (5.3%). However, the actual application is still insufficient. In addition, the BTP system is from National Taiwan Tsinghua University (Cheng, C. -H. et al., Advanced 5 94915 201114880)

Materials，2002, 14, 1409 ;美國專利公開案第此 2004076852號）所發表者，其表現出2· 76 cd/A的發光欵 率以及相對較好的色坐標（0.丨6, 〇. 14)’但對實際應用仍然 不足。如上所述，現存的單層讨科未使用主體-摻雜劑薄祺 層，就色純度及效率來說，被認為難以達到商業化。再者， 它們缺乏關於操作壽命方面的町靠數據。 根據Mitsui Chemical之專利（美國專利公開案第 了，166, 240號），下列所示之化舍物具有390至430奈米（ηιη) 之吸收光譜，並表現出4. 6 Cd/A的發光效率。然而，因具 有上述吸收波長，藍綠色（bluish green color)之發光為 可預期的。實際上，該專利所陳述的是藍綠色。因所揭露 的是對稱結構，所以不可能獲彳导純藍色。此等材料無法發 射純藍顏色，並不適用於全彩色顯示器。Published by Materials, 2002, 14, 1409; U.S. Patent Publication No. 2004076852, which exhibits a luminescence efficiency of 2.76 cd/A and relatively good color coordinates (0. 丨 6, 〇. 14 ) 'But it is still insufficient for practical applications. As described above, the existing single layer discussion does not use a host-dopant thin layer, which is considered to be difficult to commercialize in terms of color purity and efficiency. Moreover, they lack the data on the operation of the town. According to the patent of Mitsui Chemical (U.S. Patent Publication No. 166,240), the following exhibits have an absorption spectrum of 390 to 430 nm (ηιη) and exhibit a luminescence of 4.6 Cd/A. effectiveness. However, due to the above absorption wavelength, the bluish green color luminescence is expected. In fact, the patent states that it is blue-green. Because it reveals a symmetrical structure, it is impossible to obtain a pure blue color. These materials do not emit pure blue colors and are not suitable for full color displays.

關於、I彔色螢光材料，參（8-羥基喧淋）1呂（IIO(Alq)用 田 而將香豆素衍生物（coumarin derivative) 大 T)嗤0丫酮衍生物（qUinacrid〇ne derivative)、DPT 等=來當摻雜劑’摻m為百分之幾至幾十。雖然現存 電π發光材料表現出可商業化之初始發光效率，此效率卻 6 94915 201114880 _隨時間決連衰減。因為壽命問題，它們難以應用於高效能、 " 大尺寸面板。 因此，有必要開發能提供〇LED裝置滿意的操作壽命、 較佳穩定性以及優質的效能之主體材料。 【發明内容] 技術難題 因此’本發明之-目的在於提供有一種機電場發光化 。物’、具有優於現存材料之發級率及裝錢作壽命， 當的色坐標之較佳骨幹及以解決先前問題。 用_電場有機電場發繼’其使 先化“勿作為有機電場發光材料。 【貫施方式】 技術方案 在一通常態樣中，本發明楹徂组上 電埸人 ’、化予式（1)所示之有機 電场發先化合物，以及含此化合物之 因具有較佳的發光效率及優良 九 ΪΓ合物可収製造具有極優操料命之獅裝About, I 彔 萤 萤 萤 参 参 8 8 8 ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( Derivative), DPT, etc. = when the dopant is doped with a few hundred to several tens of percent. Although the existing π luminescent materials exhibit a commercially viable initial luminescence efficiency, this efficiency is 6 94915 201114880 _ decays with time. Because of life issues, they are difficult to apply to high-performance, large-size panels. Therefore, it is necessary to develop a host material that can provide a satisfactory operational life, better stability, and superior performance of the 〇LED device. SUMMARY OF THE INVENTION Technical Problem It is therefore an object of the present invention to provide an electric field illuminating. The object 'has a better backbone than the existing material and the life of the money, and the best color coordinates are used to solve the previous problem. Using the electric field of the electric field to generate the 'pre-supplement' is not used as an organic electric field luminescent material. [Comprehensive application method] Technical solution In a normal aspect, the present invention is powered by a group of people, and the formula is (1) The organic electric field precursor compound shown, and the compound containing the compound have better luminous efficiency and excellent ninth chelating compound, and can be manufactured with excellent performance.

(1) 94915 7 201114880 匕至R1S獨立地表示氫、氘、鹵素、經取代或未經取代 之（C1-C30)烷基' 經取代或未經取代之（C6_C3〇)芳基、與 -個或多健取代絲經取代之（仏⑽）環縣稠合之經 取代或未經取代之（C6_C30)芳基、經取代或未經取代之 (C3-C3G)雜芳基、經取代或未經取代之5至7元雜環院基、 與-個或多個經取代或未經取代之芳環稍合之5至7元雜 環烧基、經取代或未經取代之（C3_C3〇)環烧基、與一個或 多個經取代或未經取代之芳環稠合之（C3_C3〇)環烧基、氰 基、NR21R22、BR23R24、PR25R26、p(=〇)R27R28[其中，R21 至 R28 獨立地表示經取代或未經取代之（C1〜C30)院基、經取代或 未經取代之（C6-C3G)芳基’或録代或未經取狀（C3_C3〇) 雜方基]、RRbRcSi-[其中，Ra、R»、RC獨立地表示經取代或 ^經取代之（GK3G)絲，或錄代或未經取狀（C6_C3〇) 1基]、經取代或未經取代之（C6_⑽）芳祕卜⑽）烧基、 [其中，Y表示S或〇, aRd表示經取代或未經取代之 (C卜C30)烷基或經取代或未經取代之（C6_c3〇)芳基]、經取 代或未經取代之（C2_C3〇)稀基、經取代或未經取代之 (C2-C30)炔基、Rec(=〇)_[其中，Re表示經取代或未經取 代之（ci-⑽絲、絲代或未絲狀（G卜⑽）燒氧 基、經取代或未經取代之（C6_C3〇)芳基，或經取代或未經 取代之⑽-⑽芳氧基]、κΐ(=〇)(Η其中，Ri表示經取 代或未經取代之（cl_C3〇)燒基、經取代或未經取代之 (Cl C30)烧氧基、經取代或未經取代之⑽一c3〇)芳基，或 經取代或未經取代之（C6_C3〇)芳氧基]、竣基、硝基1 94915 8 201114880 飞52(1) 94915 7 201114880 匕 to R1S independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl 'substituted or unsubstituted (C6_C3〇) aryl, with - Substituted or substituted (C6-C30) aryl, substituted or unsubstituted (C3-C3G)heteroaryl, substituted or unsubstituted (仏(10)) cyclized substituted (C6-C30) aryl Substituted 5- to 7-membered heterocyclic, 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3_C3〇) slightly substituted with one or more substituted or unsubstituted aromatic rings a cycloalkyl group, a (C3_C3〇)cycloalkyl group fused to one or more substituted or unsubstituted aromatic rings, a cyano group, NR21R22, BR23R24, PR25R26, p(=〇)R27R28 [wherein, R21 to R28 Independently represented by a substituted or unsubstituted (C1 to C30), substituted or unsubstituted (C6-C3G) aryl 'or substituted or unsubstituted (C3_C3〇) heteroaryl group, RRbRcSi-[wherein, Ra, R», RC independently represent a substituted or substituted (GK3G) filament, or a substituted or unsubstituted (C6_C3〇) 1 group], substituted or unsubstituted ( C6_(10)) Fang (10)) an alkyl group, [wherein Y represents S or hydrazine, aRd represents a substituted or unsubstituted (C a C30) alkyl group or a substituted or unsubstituted (C6_c3 fluorene) aryl group], substituted or Unsubstituted (C2_C3〇) dilute, substituted or unsubstituted (C2-C30) alkynyl, Rec(=〇)_[where Re represents substituted or unsubstituted (ci-(10) silk, Silky or unfilamentous (GBu(10)) alkoxy, substituted or unsubstituted (C6_C3〇) aryl, or substituted or unsubstituted (10)-(10) aryloxy], κΐ (=〇) (wherein Ri represents a substituted or unsubstituted (cl_C3〇) alkyl group, a substituted or unsubstituted (Cl C30) alkoxy group, a substituted or unsubstituted (10)-c3〇) aryl group, Or substituted or unsubstituted (C6_C3〇) aryloxy], fluorenyl, nitro 1 94915 8 201114880 fly 52

/W-V r61^=/ ^ 或羥基，或者，它們可藉由具有 或不具有稠合環之（C3-C30)伸烷基或（C3-C30)伸烯基鍵聯 至相鄰取代基以形成脂環、或單環或多環之芳環； -N(Rs3)-、-S-、-0-、-Si(R54)(R55)_、-P(R56)-、 -P(=0)(Rs7)-、-C(=0)-或-B(R58)__，其中，r51 至 r58 及 r6i 至 R63與Rl至Rl8相同； 該雜環烷基及雜芳基可含一個或多個選自B、N、〇、s、 P(=0)、Si及P之雜原子；以及 m表示1或2之整數。 在本發明中，“烷基”、“烷氧基，，及其他含“烷 基”部份（moiety)之取代基包括直鏈與分支鏈種類兩者， 而且“環烷基”包括單環烴以及多環烴（例如經取代或未 經取代之金剛烷基或經取代或未經取代之(；C7_C30)雙環烷 基）。在本發明中’“芳基”表示經由除去一個氫原子而自 芳香知烴衍生的有機基，而且可包括含有4至7元，較佳 為5或6元單環或稠合環，包括數個藉由單鍵鍵聯之芳基。 芳基的具體實例包括苯基、萘基、聯苯基、蒽基、茚基、 苐基、并基、聯伸三苯基（triphenylenyl)、芘基、茈基 (perylenyl)、蒯基（chrySenyl)、稍四苯基 (naphthacenyl)、丙二烯合第基（flu〇ranthenyl)等，但不 限於此。1¾萘基包含卜萘基及2一萘基，該蒽基包含卜蒽 9 94915 201114880 基、2-蒽基及9-蒽基，且該苐基包含ι_苐基、2_第基、3 苐基、4-薙基及9-苐基。 在本發明中，術語“雜芳基”表示含有1至4個選自 B、N、0、S、P(=0)、Si及P之雜原子作為芳香族環狀骨 幹原子’及碳原子作為其他剩餘的芳香族環狀骨幹原子之 芳基。其可為5或6元單環雜芳基或由與苯環縮合而成的 多環雜芳基，而且可為部分飽合。再者，此雜芳基包括多 於一個藉由單鍵鍵結的雜芳基。雜芳基可包含二價芳義 其中’環中的雜原子可經氧化或四級化（quaternize)而开^ 成，例如，N-氧化物或四級鹽。雜芳基的具體實例包括單 環雜芳基’例如，吱喃基、嘆吩基、η比洛基、咪哇基、η 唑基、噻唑基、噻二唑基、異噻唑基、異噚唑基、卩萼。坐義 口等二唾基、三卩井基、四D井基、三嗤基、四嗤基、。夫。丫基、 吡σ定基 '吡啡基、嘧啶基、嗒D井基等；以及多環之雜芳義， 例如’苯并呋喃基、苯并噻吩基、異笨并呋喃基、苯并味 唑基、苯并噻唑基、苯并異噻唑基、笨并異噚唑基、笨并 噚唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、嗜 啭基、異0έ琳基、嗜琳基（cinnolinyl)、喧β坐嘴義 (quinazolinyl)、喹噚啉基、咔唑基、啡啶基、苯并二哼 苊基（benzodioxolyl)等、其N-氧化物（例如，吡啶基 氧化物，喹啉基N-氧化物）、其四級鹽類等，但不限於此。 在本發明中，“（C1-C30)烷基”包括（C1-C20)烷基或 (C1-C10)烷基’且“（C6-C30)芳基”包括（C6-C20)芳基或 (C6-C12)芳基。“（C3-C30)雜芳基”包括（C3-C20)雜芳基 10 94915 201114880 或（C3-C12)雜芳基，以及“（C3_C30)環烷基，，包括（C3_C2〇) '環烷基或（C3-C7)環烷基。“（C2-C30)烯基或炔基”包括 (C2-C20)晞基或炔基，或（C2-C10)烯基或炔基。 而且，在本發明中，術語“經取代或未經取代，，或 具有或不具有取代基”表示取代基可經一個或多個選自 下列所組成群組之取代基取代：氫、氘、鹵素、具有或不 具鹵素取代基之（C1-C30)烷基、（C6-C30)芳基、具有或不 具（C6-C30)芳基取代基之（C3-C30)雜芳基、5至7元雜環 烧基、與一個或多個芳環稠合之5至7元雜環烷基、（C3-C30) 環烷基、與一個或多個芳環稠合之（C3-C30)環烷基、三 (a-C30)烷基矽烷基、二（C1-C30)烷基（C6-C30)芳基矽烷 基、三（C6-C30)芳基矽烷基、（C2-C30)烯基、（C2-C30)炔 基、氰基、咔唑基、NR31R32、BR33R34、PR35R36、P(=〇)r37r38 [其 中，Rsi至R38獨立地表示（Cl-C30)烷基、（C6-C30)芳基或 (C3-C30)雜芳基]、（C6-C30)芳基（C1-C30)烧基、（C1-C30) 烷基（C6-C30)芳基、（C卜C30)烷氧基、（C1-C30)烷基硫基、 (C6-C30)芳氧基、（C6-C30)芳硫基、（C1-C30)烷氧基羰基、 (C1-C30)烷基羰基、（C6-C30)芳基羰基、（C6-C30)芳氧基 羰基、（C1-C30)烷氧基羰氧基、（C][_C3())烷基羰氧基、 (C6-C30)芳基羰氧基、（C6-C30)芳氧基羰氧基、羧基、硝 基以及羥基；或者，可鍵聯至相鄰取代基以形成環。 匕至R18H R28、R51至r58及Rsi至Re3獨立地選自氫、 氘、鹵素，烷基（例如甲基、乙基、丙基、丁基、戊基、己 基、乙基己基、庚基、辛基等）、芳基（例如苯基、萘基、 11 94915 201114880 薙基、聯苯基、菲基、聯三苯基（terphenyl)、芘基、茈基、 螺雙S基（spirobifluorenyl)、丙二烯合苐基、蒯基、聯 伸三苯基等）、與一個或多個環烷基稠合之芳基（例如丨，2一 二氫苊基（1，2-dihydroacenaphthyl)等）、雜芳基（例如二 笨并°塞吩基（(1化61^〇1：11丨(^1161^1)、二苯并呋喃基 (dibenzofuranyl)、咔唑基（carbazolyl)、吡啶、咬喃、 噻吩基（thienyl)、喹啉基（quinolyl)、三卩井基 (triazinyl)、嘧啶基（pyrimidinyl)、嗒啡基 (pyridazinyl)、喹噚啉基（quinoxalinyl)、啡啉基 (phenanthrolinyl)等）、與一個或多個芳環稠合之雜環烧 基（例如1^-苯并°比11各°定基(^61^(^71：1'〇1丨(1丨11〇)、卜苯并〇底 啶基（benzopiperidino)、N-二苯并嗎啉基 (dibenzomorpholino)、N-二苯并氮呼基（dibenzoazepino) 等）、經芳基（例如苯基、萘基、苐基、聯苯基、菲基、聯 三笨基（terphenyl)、芘基、茈基、螺雙薙基、丙二烯合 第基、蒯基、聯伸三苯基等）取代之胺基、經雜芳基（例如 二苯并°塞吩基、二苯并咬喘基、π卡嗤基、D比咬、吱喊、。塞 吩基、喹啉基、三哄基、嘧啶基、嗒哄基、喹噚啉基、啡 啉基等）取代之胺基、芳氧基（例如聯苯基氧基 (biphenyloxy)等）、芳硫基（聯苯基硫基（biphenylthi〇) 專）、芳烧基（例如聯笨甲基、三笨基曱基等）、/WV r61^=/ ^ or a hydroxyl group, or they may be bonded to an adjacent substituent by a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form An alicyclic ring, or a monocyclic or polycyclic aromatic ring; -N(Rs3)-, -S-, -0-, -Si(R54)(R55)_, -P(R56)-, -P(=0 (Rs7)-, -C(=0)- or -B(R58)__, wherein r51 to r58 and r6i to R63 are the same as R1 to Rl8; the heterocycloalkyl and heteroaryl may contain one or more a hetero atom selected from B, N, 〇, s, P(=0), Si, and P; and m represents an integer of 1 or 2. In the present invention, "alkyl", "alkoxy", and other substituents containing "alkyl" moieties include both straight-chain and branched-chain species, and "cycloalkyl" includes monocyclic a hydrocarbon and a polycyclic hydrocarbon (for example, a substituted or unsubstituted adamantyl group or a substituted or unsubstituted (; C7_C30) bicycloalkyl group). In the present invention, '"aryl group" means by removing one hydrogen atom. An organic group derived from an aromatic hydrocarbon, and may include a 4- or 7-membered, preferably 5- or 6-membered monocyclic or fused ring, including a plurality of aryl groups bonded by a single bond. Specific examples of the aryl group Including phenyl, naphthyl, biphenyl, anthracenyl, fluorenyl, fluorenyl, aryl, triphenylenyl, fluorenyl, perylenyl, chrySenyl, slightly tetraphenyl (naphthacenyl), flu〇ranthenyl, etc., but is not limited thereto. The 13⁄4 naphthyl group includes a naphthyl group and a 2-naphthyl group, and the fluorenyl group includes a dip 9 94915 201114880 base, a 2-mercapto group and a 9 a mercapto group, and the mercapto group includes a ι_mercapto group, a 2_diyl group, a 3 fluorenyl group, a 4-fluorenyl group, and a 9-fluorenyl group. In the present invention, "Heteroaryl" means 1 to 4 heteroatoms selected from B, N, 0, S, P (=0), Si and P as aromatic cyclic backbone atoms 'and carbon atoms as other remaining aromatics An aryl group of a cyclic backbone atom which may be a 5 or 6 membered monocyclic heteroaryl group or a polycyclic heteroaryl group formed by condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl group includes More than one heteroaryl group bonded by a single bond. The heteroaryl group may contain a divalent aromatic meaning in which the hetero atom in the 'ring may be oxidized or quaternized, for example, N-oxidation. Or a quaternary salt. Specific examples of heteroaryl groups include monocyclic heteroaryl 'e.g., fluorenyl, stilbene, η-l- yl, ibu- yl, η oxazolyl, thiazolyl, thiadiazolyl, Isothiazolyl, isoxazolyl, anthracene, di-salt, triterpenoid, tetra-D well, triterpene, tetradecyl, fluorenyl, pyridino-pyridyl a pyrimidine group, a fluorene D group, etc.; and a heterocyclic ring of a polycyclic ring, such as 'benzofuranyl, benzothienyl, iso-p-furanyl, benzoxazolyl, benzothiazolyl, benzo Isothiate Base, stupid and isoxazolyl, stupid and carbazolyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, eosinophilic, isoindolyl, cinnolinyl喧β quinazolinyl, quinoxalinyl, oxazolyl, phenanthryl, benzodioxolyl, etc., N-oxides thereof (eg, pyridyl oxide, quinolyl) N-oxide, its quaternary salt, and the like, but is not limited thereto. In the present invention, "(C1-C30)alkyl" includes (C1-C20)alkyl or (C1-C10)alkyl' and "(C6-C30)aryl" includes (C6-C20) aryl or (C6-C12) aryl. "(C3-C30)heteroaryl" includes (C3-C20)heteroaryl 10 94915 201114880 or (C3-C12)heteroaryl, and "(C3_C30)cycloalkyl, including (C3_C2〇) 'cycloalkane Or (C3-C7)cycloalkyl. "(C2-C30)alkenyl or alkynyl" includes (C2-C20)nonyl or alkynyl, or (C2-C10)alkenyl or alkynyl. In the present invention, the term "substituted or unsubstituted, with or without a substituent" means that the substituent may be substituted with one or more substituents selected from the group consisting of hydrogen, hydrazine, halogen, and having Or a (C1-C30)alkyl group having no halogen substituent, a (C6-C30) aryl group, a (C3-C30) heteroaryl group having or not having a (C6-C30) aryl substituent, a 5- to 7-membered heterocyclic ring a pyridyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings, a (C3-C30) cycloalkyl group, a (C3-C30) cycloalkyl group fused to one or more aromatic rings, Tris(a-C30)alkyldecanealkyl, di(C1-C30)alkyl(C6-C30)aryldecylalkyl, tris(C6-C30)aryldecylalkyl, (C2-C30)alkenyl, (C2 -C30) alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=〇)r37r38 [its Rsi to R38 independently represent (Cl-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl], (C6-C30)aryl (C1-C30)alkyl, (C1 -C30) alkyl (C6-C30) aryl, (C-C30) alkoxy, (C1-C30)alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C) [_C3()) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxy, nitro and hydroxy; or, may be bonded to Adjacent substituents form a ring. 匕 to R18H R28, R51 to r58 and Rsi to Re3 are independently selected from hydrogen, hydrazine, halogen, alkyl (eg methyl, ethyl, propyl, butyl, pentyl, hexyl) , ethylhexyl, heptyl, octyl, etc.), aryl (eg phenyl, naphthyl, 11 94915 201114880 fluorenyl, biphenyl, phenanthryl, terphenyl, fluorenyl, fluorenyl, Spirofluorenyl, propadienyl, fluorenyl, triphenyl, etc., fused to one or more cycloalkyl (e.g., hydrazine, 1,2-dihydroacenaphthyl, etc.), heteroaryl (e.g., diphtho-pyranyl ((1, 61^〇1:11丨(^1161^1), Dibenzofuranyl, carbazolyl, pyridine, gnashing, thienyl, quinolyl, triazinyl, pyrimidinyl, morphine Pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., a heterocyclic alkyl group fused to one or more aromatic rings (eg, 1^-benzoxine ratio of 11 ° ° ^61^(^71:1'〇1丨(1丨11〇), benzopiperidino, N-dibenzomorpholino, N-dibenzoxazinyl (dibenzoazepino), etc., aryl (e.g., phenyl, naphthyl, anthracenyl, biphenyl, phenanthryl, terphenyl, fluorenyl, fluorenyl, spirobiindyl, alkadiene) Substituted amino group, heteroaryl group (for example, dibenzo-thenyl, dibenzo-thenazoyl, π-carbyl, D-bit, scream, . a substituted amino group, an aryloxy group (e.g., biphenyloxy), etc., a thiophenyl group, a quinolyl group, a tridecyl group, a pyrimidinyl group, a fluorenyl group, a quinoxaline group, a porphyrin group, or the like, An arylthio group (biphenylthi〇), an aryl group (eg, a benzyl group, a trisyl group, etc.),

12 94915 201114880 如化學式1所定義般經取代。 根據本發明之有機電場發光化合物可以下列化合物 例示之，但不限於此：12 94915 201114880 Replaced as defined in Chemical Formula 1. The organic electroluminescent compound according to the present invention can be exemplified by the following compounds, but is not limited thereto:

13 94915 20111488013 94915 201114880

14 94915 20111488014 94915 201114880

15 94915 20111488015 94915 201114880

16 94915 20111488016 94915 201114880

17 94915 201114880 根據本發明之有機電場發光化合物可由流程圖1製 備，但不限於此。 流程圖117 94915 201114880 An organic electroluminescent compound according to the present invention can be prepared by the flow chart 1, but is not limited thereto. Flow chart 1

其中Ri至Rie、A及B與化學式1中的定義相同。 在另一通常態樣中，本發明提供一種有機電場發光裝 置’包括：第-電極；第二電極；以及—層或多層有機層， 係》又於第一電極以及第二電極之間，其中，有機層包括一 ，或多個化學式⑴所示之有機電場發光化合物。此有機電 昜發光化合物係用來作為電場發光層中的主體材料。 有機層可包括電場發光層，該場發光層除了包含一個 或多個化學式⑴所示的錢電場發光化合物以外，還包含 個或多個摻雜劑。本發明之有機電場發錄置中使用的 94915 18 201114880 摻雜劑並無特別限制。 較佳者，本發明之有機電場發光U中使㈣接 - 可選自化學式（2)至（4)表示之化合物： 月Wherein Ri to Rie, A and B are the same as defined in Chemical Formula 1. In another general aspect, the present invention provides an organic electric field light-emitting device 'comprising: a first electrode; a second electrode; and - a layer or layers of organic layers, between the first electrode and the second electrode, wherein The organic layer includes one or more organic electroluminescent compounds represented by the chemical formula (1). This organic electroluminescent compound is used as a host material in an electroluminescent layer. The organic layer may include an electric field luminescent layer containing one or more dopants in addition to one or more of the money electric field luminescent compounds represented by the chemical formula (1). The 94915 18 201114880 dopant used in the organic electric field recording apparatus of the present invention is not particularly limited. Preferably, the organic electric field illuminating U of the present invention is (4)-selectable from the compounds represented by the chemical formulas (2) to (4):

Αγ13—Ν^ΑΓ11 其中，Αγ13—Ν^ΑΓ11 where,

Arn及Au獨立地表示經取代或未經取代之（c卜C3〇) 烷基、經取代或未經取代之（C6-C30)芳基、經取代或未經 取代之（C4-C30)雜芳基、經取代或未經取代之（C6_C3〇)芳 基胺基、（C1-C30)烷基胺基、經取代或未經取代之5至7 元雜環烷基、與一個或多個經取代或未經取代之芳環稠合 之5至7元雜環烷基、經取代或未經取代之（C3_C3〇)環烷 基，或與一個或多個經取代或未經取代之芳環稠:: (C3-C3G)環烧基，或者，―及Ari2藉由具有或不具^ 環之（C3-C30)伸烷基或（C3-C30)伸烯基鍵聯以形成脂環、 或單環或多環之芳環； g &、 於c為1時，Aru表示經取代或未經取代之 芳基、經取代或未經取代2(C4_C30)雜芳基或選自 構之取代基： ％ 19 94915 201114880Arn and Au independently represent a substituted or unsubstituted (c-C3〇) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (C4-C30) hetero An aryl group, a substituted or unsubstituted (C6_C3 fluorene) arylamino group, a (C1-C30)alkylamino group, a substituted or unsubstituted 5 to 7 membered heterocycloalkyl group, and one or more a substituted or unsubstituted aromatic ring fused 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3_C3 fluorene) cycloalkyl, or substituted with one or more substituted or unsubstituted aromatic Ring thick:: (C3-C3G) cycloalkyl, or, and - and Ari2 are bonded to each other by a (C3-C30)alkylene group or a (C3-C30)alkylene group to form an alicyclic ring, Or a monocyclic or polycyclic aromatic ring; g &, when c is 1, Aru represents substituted or unsubstituted aryl, substituted or unsubstituted 2(C4_C30)heteroaryl or selected from Substituent: % 19 94915 201114880

於C為2時，An3表示經取代或未經取代之（C6_C3〇) 伸方基、經取代或未經取代之（C4_C3〇)伸雜芳基或選自下 列結構之取代基：When C is 2, An3 represents a substituted or unsubstituted (C6_C3〇) stretch group, a substituted or unsubstituted (C4_C3〇) heteroaryl group or a substituent selected from the following structures:

Aru及Ans獨立地表示經取代或未經取代之別） 伸芳基或經取代或未經取代之（C4-C30)伸雜芳基； 至R2。3獨立地表示氫、氘、經取代或未經取代之 (Cl C30)烷基，或經取代或未經取代之（C6—c加）芳基； d表不從1至4之整數； e表示0或1之整數；以及Aru and Ans independently represent substituted or unsubstituted aryl or substituted or unsubstituted (C4-C30) heteroaryl; to R2. 3 independently represents hydrogen, deuterium, substituted or Unsubstituted (Cl C30) alkyl, or substituted or unsubstituted (C6-c plus) aryl; d is not an integer from 1 to 4; e represents an integer of 0 or 1;

其中， (4) 、“至r214獨立地表示氫m經取代或未經取 代之（C1-G30)烧基、經取代或未經取代之⑽―芳基、 經取代或未經取代之（C；3_⑽）雜芳基、經取代或未經取代 =至7元雜環絲、與—個或多個經取代或未經取代之 方％稠合之5至7元雜環烧基、經取代或未經取代之 (C3-C3G)環絲、與—個或多侧取代或未經取代之芳環 94915 20 201114880 • 稠合之（C3-C30)環烷基、氰基、NR3。丨R3〇2、BR3〇3R3(h、PR3〇5R3〇6、 • P(=0)R3〇7R3()8 [其中，R3D1至R3〇8獨立地表示經取代或未經取 • 代之（C1-C30)烷基、經取代或未經取代之（C6-C30)芳基’ 或經取代或未經取代之（C3-C30)雜芳基]、經取代或未經取 代之三（C卜C30)烷基矽烷基 '經取代或未經取代之二 (C1-C30)烷基（C6-C30)芳基矽烷基、經取代或未經取代之 三（C6-C30)芳基矽烷基、經取代或未經取代之（C6_C3〇)芳 基（C1-C30)烷基、經取代或未經取代之（C1-C30)烷氧基、 經取代或未經取代之（C1-C30)烷基硫基、經取代或未經取 代之（C6-C30)芳氧基、經取代或未經取代之（C6-C30)芳硫 基、經取代或未經取代之（C1-C30)烷氧基羰基、經取代或 未經取代之（C1-C30)烷基羰基、經取代或未經取代之 (C6-C30)芳基叛基、經取代或未經取代之（C2-C30)稀基、 經取代或未經取代之（C2-C30)炔基、經取代或未經取代之 (C6-C30)芳氧基羰基、經取代或未經取代之（C1-C30)烷氧 基羰氧基、經取代或未經取代之（C1-C30)烷基羰氧基、經 取代或未經取代之（C6-C30)芳基羰氧基、經取代或未經取 代之（C6-C30)芳氧基羰氧基、羧基、硝基或羥基，或者， 它們各自可藉由具有或不具有稠合環之（C3-C30)伸烷基或 (C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或 多環之芳環。 電％發光層為產生電場發光處，而且可由單層或雙層 成更多層形成。當使用如本發明之主體-摻雜劑系統時，如 本發明之電場發光主體對發光效率提供了顯著的提升。捧 94915 21 201114880 雜濃度可為〇. 5至1 〇 Wt%。與其他現存主體材料相比時， 如本發明之電場發光主體提供了優異的電洞及電子傳導 率，以及極優越的穩定性與顯著提升的發光效率和操作壽 命。 化學式（3)或化學式（4)表示之摻雜劑化合物可由第 10-細，23442號韓國專财請案中揭露之化合物例示 之。更佳者’其可選自下列結構，但不限Wherein, (4), "to r214" independently represent (C1-G30)alkyl, substituted or unsubstituted (10)-aryl, substituted or unsubstituted (C). ; 3—(10))heteroaryl, substituted or unsubstituted=to 7-membered heterocyclic filament, 5 to 7-membered heterocyclic alkyl group fused with one or more substituted or unsubstituted squares, substituted Or unsubstituted (C3-C3G) cyclofilament, with one or more side substituted or unsubstituted aromatic rings 94915 20 201114880 • fused (C3-C30) cycloalkyl, cyano, NR3. 丨R3 〇2, BR3〇3R3 (h, PR3〇5R3〇6, • P(=0)R3〇7R3()8 [where R3D1 to R3〇8 independently represent substituted or unsubstituted (C1- C30) alkyl, substituted or unsubstituted (C6-C30) aryl ' or substituted or unsubstituted (C3-C30)heteroaryl], substituted or unsubstituted three (C Bu C30) Alkylalkylalkyl 'substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)aryldecyl, substituted or unsubstituted tris(C6-C30)aryldecyl, by Substituted or unsubstituted (C6_C3〇) aryl (C1-C30) alkyl, substituted Or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C1-C30)alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or Unsubstituted (C6-C30) arylthio, substituted or unsubstituted (C1-C30) alkoxycarbonyl, substituted or unsubstituted (C1-C30) alkylcarbonyl, substituted or not Substituted (C6-C30) aryl thiol, substituted or unsubstituted (C2-C30), substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (C1-C30) alkoxycarbonyloxy, substituted or unsubstituted (C1-C30)alkylcarbonyloxy, substituted or Unsubstituted (C6-C30) arylcarbonyloxy, substituted or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxy, nitro or hydroxy, or they may each have or A (C3-C30)alkylene group having no fused ring or a (C3-C30)alkylene group bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring. Produce an electric field, and can be single or double The formation of more layers. When using the host-dopant system of the present invention, the electroluminescent body of the present invention provides a significant improvement in luminous efficiency. The holding density of 94915 21 201114880 can be 〇. 5 to 1 〇 Wt%. When compared to other existing host materials, the electroluminescent body of the present invention provides excellent hole and electron conductivity, as well as excellent stability and significantly improved luminous efficiency and operational life. The dopant compound represented by the chemical formula (3) or the chemical formula (4) can be exemplified by the compound disclosed in the Japanese Patent Application No. 10-43, No. 23442. More preferably, it may be selected from the following structures, but is not limited

94915 22 20111488094915 22 201114880

除了化學式（1)所示之有機電場發光化合物之外，本 發明之有機電場發光裝置可同時更進一步包括一種或多種 選自芳基胺化合物以及苯乙烯基芳基胺（styrylarylamine) 23 94915 201114880 化合物組成之群組之化合物。芳基胺化合物或苯乙烯基芳 基胺化合物可以第 10-2008-0123276、10-2008-0107606 或10-2008-01 18428號韓國專利申請案中揭露者例示之， 但不限於此。 再者，在本發明之有機電場發光裝置中，除了化學式 (1)所示之有機電場發光化合物之外，有機層可更進一步包 括一種或多種選自第1族之有機金屬、第2族、第4週期 與第5週期之過渡金屬、鑭系金屬與d_過渡元素 (d-transition elements)組成之群組之金屬。 再者，除了該有機電場發光化合物之外，該有機層可 包括一層或多層有機電場發光層，該有機電場發光層同時 發射藍、綠或紅光’以達成發白光之有機電場發光裝置。 該發射藍、綠或紅光之化合物可以第1〇_2〇〇8-0123276、 10-2008-0107606 或 10-2008-0118428 號韓國專利申請案 中所揭露者例示，但不限於此。 在本發明之有機電場發光裝置中，可將選自硫屬元素 化合物層（chalcogenide layer)、金屬鹵化物層以及金屬 氧化物層的層體（後文後稱為“表面層”）設置於電極對中 的一個或二個電極之内表面。更明確地說，矽或鋁之硫屬 元素化合物（包括氧化物）層可設置於電場發光介質層的陽 極表面，且金屬函化物層或金屬氧化物層可設置於該電場 發光介質層的陰極表面。可由此得到操作穩定性。 硫屬元素化合物可為’例如，Si 〇x(1 < 2 )、A1 Ox (Η 1. 5)、SiON、SiAlON等。金屬鹵化物可為，例如， 94915 24 201114880 iIn addition to the organic electroluminescent compound of the formula (1), the organic electroluminescent device of the present invention may further comprise one or more compounds selected from the group consisting of arylamine compounds and styryl arylamine 23 94915 201114880 compounds. a group of compounds. The arylamine compound or the styrylarylamine compound can be exemplified by the Korean Patent Application No. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto. Furthermore, in the organic electroluminescence device of the present invention, in addition to the organic electroluminescent compound of the formula (1), the organic layer may further comprise one or more organometallics selected from the group 1, the second group, A metal of a group consisting of transition metals, lanthanide metals, and d-transition elements of the fourth and fifth cycles. Furthermore, in addition to the organic electroluminescent compound, the organic layer may comprise one or more layers of an organic electroluminescent layer that simultaneously emits blue, green or red light to achieve an organic light-emitting device that emits white light. The compound which emits blue, green or red light can be exemplified by the Korean Patent Application No. Hei. No. Hei. No. Hei. Hei. No. Hei. Hei. In the organic electric field light-emitting device of the present invention, a layer body selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") may be provided on the electrode. The inner surface of one or both of the electrodes. More specifically, a chalcogen compound (including oxide) layer of bismuth or aluminum may be disposed on the anode surface of the electric field luminescent medium layer, and a metal functional layer or a metal oxide layer may be disposed at the cathode of the electric field luminescent medium layer. surface. Operational stability can thus be obtained. The chalcogen compound may be, for example, Si 〇 x (1 < 2 ), A1 Ox (Η 1.5), SiON, SiAlON or the like. The metal halide can be, for example, 94915 24 201114880 i

LiF、MgFz、CaF2、稀土金屬氟化物等。金屬氧化物可為例 -如，Cs2〇、Li2〇、MgO、SrO、BaO、CaO 等。 在根據本發明之有機電場發光裝置中，較佳者亦可於 電極對之至少-表面安置如是所製造之電子傳輸化合物與 還原摻雜劑之混合區，或電洞傳輸化合物與氧化捧雜劑之 混合區。在此種情形時，由於電子傳輸化合物還原成陰離 子，加速電子從混合區注入與傳輸至電場發光介質。此外， 由於電洞傳輸化合物氧化成陽離子，加速電洞從混合區注 入與傳輸至電場發紐質。較佳的氧化摻_包括各種路 易士酸（Lewis acid)及接受體化合物 compound)。較佳的還原摻雜劑包括驗金屬、驗金屬化合 物、鹼土金屬、稀土金屬，及其混合物。 .再者’具有二層或更多層之電場發光層之發白光之有 機電場發光裝置，可藉由佶用请 製造之。 猎由❹_摻雜層作電荷產生層而 有利效果 由於根據本發明之有機 發光效率與優質的操作壽命 操作壽命之0LED裴置。 發明模式 電場發光化合物具有良好的 其可使用於製造具非常優異 本發明係藉由參照本發明 製備方法，以及使用該化合I:讓光化合物、其 步加以說明。然而，接下來的·、#電场發光特性進-的，並無限制本發明範圍之意^例储供作為說明之目 94915 25 201114880 [製備例1]化合物1的製備LiF, MgFz, CaF2, rare earth metal fluoride, and the like. The metal oxide may be exemplified by, for example, Cs2〇, Li2〇, MgO, SrO, BaO, CaO, or the like. In the organic electric field light-emitting device according to the present invention, it is preferable that at least the surface of the electrode pair be such that a mixed region of the electron transport compound and the reducing dopant produced, or a hole transport compound and an oxidation dopant are disposed. Mixed area. In this case, since the electron transporting compound is reduced to an anion, accelerated electrons are injected and transported from the mixed region to the electric field illuminating medium. In addition, due to the oxidation of the hole transporting compound to the cation, the accelerating hole is injected and transported from the mixing zone to the electric field. Preferred oxidative dopings include various Lewis acids and acceptor compounds. Preferred reducing dopants include metal detectors, metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Further, an organic electric field illuminating device which emits white light having two or more layers of an electric field illuminating layer can be manufactured by using it. Hunting from the ❹-doped layer as the charge generating layer is advantageous because of the organic light-emitting efficiency according to the present invention and the excellent operating life of the OLED. Mode of the Invention The electroluminescent compound is excellent in that it can be used in the production of the present invention. The present invention is made by referring to the preparation method of the present invention, and the use of the compound I: the photocompound is explained. However, the following electric field luminescence characteristics are not limited to the scope of the present invention. The storage is provided for illustrative purposes. 94915 25 201114880 [Preparation 1] Preparation of Compound 1

化合物1 -1的製備 將 2, 7-二>臭基萘（2, 7-dibromonaphthalene)(20 公克 (g) ’ 128. 02 毫莫耳（mmol))溶解於 〇MF(200 毫升（mL))中。 接著’在室溫下緩慢地加入NBS(50.1g，281.65 mmol)。 室溫下攪拌24小時後’在減壓下蒸餾此有機溶劑。加入蒸 餾水後，用EA萃取獲得化合物卜1(36 g，114. 64 mmol， 89. 56 %)。 化合物1-2的製備 將化合物1-1(36 g，114.64 mmol)、苯基硼酸 (phenylboronic acid)(41. 9 g，343. 92 mmol)、肆（三苯 基膦）Ιε (tetrakis(triphenylphosphine)palladium) (Pd(PPh〇4，6. 6 g，5. 73 mmol)、3 M K2C〇3 (115 mL)、 甲苯（500 mL)與乙醇（200 mL)混合，接著在回流下攪拌。 經6小時反應接著冷卻至室溫後，加入蒸餾水。用EA萃取 並用MgSCU乾燥後，在減壓下蒸餾，接著以管柱分離法獲 得化合物 1-2 (29 g，94. 02 mmol，82. 48 %)。 化合物1-3的製備 將 KMn〇4(74. 2 g，470.13 mmol)與蒸顧水（70 mL)混 26 94915 201114880 合，然後將°比°定（400 mL)與化合物1-2(29 g)加入其中。 加熱至130 2C後，將KMn〇4(20 g)與蒸餾水（60 mL)間隔 ， 30分鐘加入4次。5小時之後，加入400 mL蒸德水，並在 回流下攪拌此混合物12小時。趁熱在減壓下過濾此反應混 合物，接著用蒸餾水清洗之。用EA萃取並用MgSCU乾燥後， 在減壓下蒸餾，接著以管柱分離法獲得化合物1-3 (16 g， 43. 43 mmol ’ 46.20 %)。 化合物1-4的製備 將化合物1-3 (16 g，43. 43 mmol)溶解於曱醇（300 mL) 中，然後在室溫下緩慢地加入S0C12。在回流下攪拌12小 時後，加入蒸镏水。用EA萃取並用MgSCh乾燥後，在減壓 下蒸餾，接著以管柱分離法獲得化合物1-4(9 g，22.70 mmol ， 52.79 %)。 化合物1-5的製備 將化合物卜4(9 g，22. 70 mmol)溶解於 THF(400 mL) 中，然後在室溫下缓慢地加入溴化曱鎂（53 mL，158. 91 _〇1，3. 0 Μ於二***中）。在60SC下攪拌12小時後，緩 慢地加入蒸餾水。用EA萃取並用MgS〇4乾燥後，在減壓下 蒸餾，接著以管柱分離法獲得化合物1-5(5. 6 g，14. 12 mmol ， 62.21 %)。 化合物1-6的製備 將化合物 1-5(5.6 g，14. 12 mmol)、乙酸（100 mL) 及H3P〇4(200 mL)混合，然後在回流下攪拌。經過10小時， 冷卻至室溫後，加入蒸顧水。用NaOH水溶液中和之後， 27 94915 201114880 用EA萃取並用MgS04乾燥後，在減壓下蒸餾，接著以管柱 層析法獲得化合物 1-6(2. 5 g，6. 93 mmol，49. 11 %)。 化合物1-7的製備 將化合物 1-6(2. 5 g ’ 6. 93 mmol)溶解於 THF(50 mL) 中，然後加入NBS (1· 35 g，7. 62 mmol)。經過12小時搜 拌後’令此有機溶劑在減壓下蒸餾。以管柱分離法獲得化 合物 1-7(2. 7 g，6. 14 mmol，88. 67 %)。 化合物1的製備 將化合物 1-7(2. 7 g ’ 6. 14 mmol)、9-苯基-10-蒽硼 酸（2. 19 g’ 7· 37mmol)、肆（三苯基膦）鈀（Pd(PPh3)4，〇. 35 g，0. 30 mmol)、3 M K2CO3水溶液（6 mL)、曱苯（40 mL)以 及乙醇（15 mL)混合，然後在回流下攪拌。經過8小時反應 及冷卻至室溫後，加入蒸餾水。用EA萃取並用MgS〇4乾燥 後，在減壓下蒸餾，接著以管柱分離法獲得化合物丨（2 4 g，3. 91 mmol，63.78 %)。 化合物1至102係按照製備例i的步驟製備而成。藉 此製成的有機電場發光化合物之卞_R& MS/FAB數據列 示於表1之中。 94915 28 201114880 丨表1 化合 物 Ή NMR (CDCls, 200 MHz) MS/FAB 實測值 計算值 1 (5 = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 44(7H, m), 7. 51-7. 52(4H, m), 7. 61(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m), 8. 09C2H, m) 612.80 612.28 2 ά = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 44(6H, m), 7. 55(2H, m), 7.6K3H, m), 7.9K4H, m), 7.95C1H, s), 7.99-8.09(5H, m), 8.42(1H, m), 8.55(1H, m) 662.86 662. 30 4 (5 = 1.78C12H, s), 2.34C3H, s), 7.1(1H, m), 7.24-7.44C12H, m), 7.61C2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m) 626. 83 626. 30 6 ^ = 1.78C12H, s), 7.1(1H, ra), 7. 24-7. 25(6H, n), 7.39-7.44(7H, m), 7. 51-7. 52(4H, m), 7.61(2H, in), 7.9K4H, m), 7.95(1H, s), 7. 99(1H, in), 8. 09(2H, m) 688. 90 688. 31 10 5 = 1.78(12H, s), 7(1H, m), 7.1(1H, m), 7. 24-7. 26(3H, m), 7. 39-7. 44(6H, m), 7. 51(1H, m), 7.6K2H, in), 7.91(4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m), 8.5(1H, m) 613.79 613.28 16 (5 = 1.78(12H, s), 7.1(1H, m), 7.24-7.3(4H, m), 7.39-7.44(8H, m), 7.61(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, in), 8.09(2H, m) 630. 79 630. 27 21 (5 = 1.78C12H, s), 7. 1(1H, in), 7.24(2H, in), 7.39-7.44(8H, m), 7.51(4H, m), 7.6K2H, m), 7.91(4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m), 8.28(4H, m) 767. 96 767. 33 25 5 = 1.78(12H, s), 7.1(1H, m), 7. 24-7. 25(3H, m), 7.33-7.5C10H, m), 7.58-7.61(4H, m), 7. 69(1H, m), 7. 77(1H, m), 7. 87-7. 94(6H, m), 7.95C1H, s), 7.99(1H, m), 8.09(2H, in), 8.55C1H, m) 777. 99 777. 34 31 δ = 1.78C12H, s), 7.1(1H, m), 7.24(2H, in), 7.39-7.44(6H, m), 7.58-7.6K3H, m), 7.79-7.8C2H, m), 7.9-7.9K5H, m), 7.95(1H, s), 7.96-7. 99(2H, m), 8.09-8. 1(4H, m), 736. 94 736.31 29 94915 201114880 8. 42(2H, m) 32 <5 = 1.78(12H, s), 7. 1(1H, m), 7. 24-7. 33(5H, m), 7.4-7.5C7H, m), 7.61-7.63(3H, m), 7.9-7.94C5H, m), 7.95(1H, s), 7.99(1H, m), 8. 09-8.12(3H, m), 8. 55(1H, m) 701.89 701.31 33 (5 = 1.78C12H, s), 7.1(1H, m), 7. 24-7. 25(6H, m), 7.39-7.52(13H, m), 7.61(2H, m), 7. 85(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m), 8. 09(2H, m) 764. 99 764. 34 36 5 = 1.78(18H, s), 7.1-7.14C2H, m), 7. 24(2H, m), 7.39-7.44(6H, m), 7.51-7.54(2H, m), 7.61(2H, m), 7.69(1H, m), 7.83(1H, m), 7. 91(4H, m), 7.95C1H, s), 7. 98-7. 99(2H, m), 8.09(3H, m), 8.15(1H, m), 8.52(1H, m) 779. 02 778. 36 40 5 = 1.78C12H, s), 7.1(1H, m), 7. 24-7. 5(12H, m), 7.61-7.68(5H, m), 7.79(2H, m), 7.91-7.94C5H, m), 7.95(1H, s), 7.99(1H, m), 8. 09-8.12(3H, m), 8. 55(1H, m) 777. 99 777. 34 41 (5 = 1.72C12H, s), 1.78(12Η, s), 7.1(1H, m), 7. 24(3H, m), 7. 39-7. 44(7H, m), 7. 61-7. 63(4H, m), 7.69C1H, s), 7.77(2H, s), 7.77(0H, m), 7.91-7.93C5H, m), 7.95(1H, s), 7.99(1H, m), 8. 09(3H, m) 845.12 844. 41 45 5 = 1.72C6H, s), 1.78C12H, s), 7.1(1H, m), 7. 24(2H, m), 7. 33-7. 44(9H, m), 7. 61(2H, m), 7.71C1H, m), 7.9K4H, m), 7.95(1H, s)， 7.97(1H, s), 7.99(1H, m), 8.09(2H, m), 8.78(1H, s), (H,) 729. 95 729. 34 47 5 = 1.78(12H, s), 6.97(2H, m), 7.1(1H, m), 7.16-7.24C8H, m), 7. 38(4H, m), 7. 44(2H, m), 7.61(2H, m), 7.88-7.9(4H, m), 7.95C1H, s), 7. 99(1H, m), 8. 09(2H, m) 733. 96 733. 28 54 5 = 1.72C6H, s), 1.78C12H, s), 6.55C1H, m), 6.61-6.63C3H, m), 6. 73(1H, m), 6.81(1H, m), 7.02-7.1(3H, m), 7.2-7.24(4H, m), 7.36-7.44(7H, m), 7.6K3H, m), 7.91(4H, m), 7.95(1H, s), 7.99C1H, m), 8.09(2H, m) 820. 07 819.39 30 94915 201114880 55 δ = 1.78C12H, s), 7.1(1Η, m), 7. 24-7. 25(6H, m), 7. 39-7. 44(6H, m), 7. 55(2H, m), 7. 61(3H, m), 7. 91(4H, m), 7. 95(1H, s), 7. 99-8. 09(5H, m), 8.42C1H, m), 8.55(1H, m) 738. 95 738. 33 56 5 = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 48(8H, m), 7. 57-7. 61 (6H, m), 7.7-7.73C2H, m), 7.91-7.92(5H, m), 7.95(1H, s), 7.99-8C3H, m), 8.09(2H, m) 738. 95 738. 33 57 5 = 1.72(6H, s), 1.78C12H, s), 7. 1(1H, m), 7. 24-7. 28(3H, m), 7. 38-7. 47(9H, m), 7. 55(1H, in), 7.61-7.63(3H, m), 7.77(1H, m), 7. 85-7. 93(8H, m), 7.95C1H, s), 7. 99(1H, m), 8. 09(2H, m) 805. 06 804. 38 59 5 = 1.78(12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7.44(11H, m), 7.51-7. 52(4H, m), 7.61 (2H, m), 7.91(8H, m), 7.95(1H, s), 7.99C1H, m), 8.09(2H, m) 789.01 788. 34 60 <5 = 1.78(12H, s), 7.1(1H, m), 7. 24-7. 25(6H, in), 7.39-7.44C11H, m), 7.51-7.52(4H, m), 7.61(2H, m), 7.9K8H, m), 7.95(1H, s), 7. 99(1H, in), 8. 09(2H, m) 865.11 864. 38 62 5 = 1.78C12H, s), 7. 1(1H, m), 7.24(2H, m), 7.39-7.44(7H, m), 7.5K2H, in), 7.61(4H, m), 7.79(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99C1H, m), 8.09(2H, m), 8.42(2H, m), 8.5K2H, in) 738. 95 738. 33 63 <5 = 1.78(12H, s), 6. 63(4H, m), 6. 69(2H, m), 6.81C2H, m), 7.1(1H, m), 7.2-7.24(6H, m), 7.39-7.44(6H, m), 7.54(2H, m), 7.61(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m), 8. 09(2H, m) 780.01 799. 36 64 δ = 1.78(12H, s), 7. 1-7.11 (7H, m), 7.24-7.44(21H, m), 7.61(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m) 855.11 855.39 65 5 = 1.78(12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 44C6H, m), 7. 55(2H, m), 7. 61-7. 64(3H, ii), 7.74-7.84(6H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m) 716.91 716.31 31 94915 201114880 70 (5 = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 44C6H, m), 7. 61(2H, m), 7.91C4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m) 617.83 617.31 75 5 = 1.78(12H, s), 2.34(3H, s), 7. 1(1H, m), 7. 24(2H, m), 7. 39-7. 44(7H, m), 7.51-7. 52(4H, m), 7.6K1H, m), 7.9K4H, m), 7.95(1H, s), 7. 97-7. 99(2H, m), 8. 09(1H, m) 626. 83 626.30 77 5 = 1.78C12H, s), 2.34C6H, s), 7. 1(1H, m), 7. 24(2H, m), 7. 39-7. 41 (7H, m), 7. 51-7. 52(4H, m), 7.9K4H, m), 7.95(1H, s), 7. 97-7. 99(3H, m) 640. 85 640.31 80 5 = 1.78(12H, s), 7. 1(1H, m), 7.24(1H, m), 7. 39-7. 44(6H, m), 7. 51-7. 52(4H, m), 7.6K1H, m), 7.69(1H, m), 7.86-7.91(5H, m), 7.95(1H, s), 7.99(1H, m), 8.09(1H, m), 8.27(1H, m) 637.81 637. 28 82 δ = 1.78C12H, s), 7.1(1H, m), 7. 39-7. 41(7H, m), 7. 51-7.52(12H, m), 7. 69(2H, m), 7. 83(2H, m), 7.91(4H, m), 7.95(1H, s), 7.99(1H, m), 8.15C2H, m) 764. 99 764. 34 83 δ = 1.78C12H, s), 7. 1(1H, m), 7.24(2H, m), 7. 39-7. 44(6H, m), 7. 51-7. 52(8H, m), 7.61C3H, m), 7.9K2H, m), 7.95(1H, s), 7.97-7.99(2H, m), 8.09-8.13(3H, m) 688. 90 688.31 86 (5 = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7.41-7.44(5H, m), 7.51-7.52(12H, m), 7.6K4H, m), 7.95C1H, s), 7.97-7.99(3H, m), 8.09-8.13(4H, m) 764. 99 764. 34 87 5 = 7.39-7.41 (5H, m), 7. 5-7. 52(8H, m), 7.58(1H, m), 7.8(1H, m), 7.9K4H, m), 7.98C2H, m), 8.08(1H, s), 8.45(2H, m) 592. 77 592.13 93 5 = 7.32-7.4K7H, m), 7.5-7.52(6H, m), 7. 59(1H, m), 7. 66(2H, m), 7. 89-7. 91(5H, tn), 7.98C1H, m), 8.08(1H, s), 8.45(1H, m) 576. 70 576.15 98 5 = 1.78(12H, s), 2.45(6H, s), 7. 1(1H, m), 7. 24-7. 25(4H, m), 7.41-7.44(3H, m), 7. 51-7. 52(4H, m), 7. 61(2H, m), 7. 7(2H, m), 7.85C2H, m), 7.95(1H, s), 7.99C1H, m), 8.09C2H, m) 640. 85 640. 31 32 94915 201114880 99 5 = 0.9(12H, m), 1.9K8H, m), 7.1(1H, m), 7. 24(2H, m), 7. 39-7. 44(7H, m), 7. 51-7. 52(4H, m), 7.61(2H, m), 7.91(4H, m), 7.95(1H, s), 7. 99(1H, m), 8. 09(2H, m) 668.91 668. 34 100 δ = 1.84C12H, s), 7.1(1H, m), 7. 39-7. 41(5H, m), 7.51-7.58C10H, m), 7. 91(4H, m), 7. 95(1H, s), 7.97-8.01(5H, m), 8.28(2H, m) 712.92 712.31 101 5 = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7.39-7.44C6H, m), 7. 51-7. 52(4H, m), 7. 61(2H, m), 7.82-7.91(5H, m), 7.95(1H, s), 7.99(1H, b), 8. 09-8.12(3H, m), 8. 93(1H, m) 662. 86 662. 30 102 5 = 1.78C24H, s), 7.1(2H, m), 7.24(4H, m), 7.39-7.44C8H, m), 7.61(4H, m), 7.9K4H, m), 7. 95C2H, s), 7.99C2H, m), 8.09(4H, m) 895.18 894. 42 [實施例1]使用本發明之有機電場發光化合物之0LED裝 置之製造 用根據本發明之有機電場發光化合物製造了 0LED裝 置。 首先，對獲得自0LED用玻璃（Samsung Corning製造） 之透明電極ΙΤ0薄膜，依序用三氯乙烯、丙酮、乙醇及蒸 餾水施以超音波清洗，並存放於異丙醇中備用。 接著，將ΙΤ0基材安置於真空氣相沉積設備的基材夾 中，並將4,4’，4”-參（N，N-(2-萘基）-苯基胺基）三苯基胺 (2-TNATA)置於真空氣相沉積設備之一小室（cell)中，接著 換氣至腔室内真空至1(Γ6托（torr)。然後，施加電流至小 室以蒸發2-TNATA，藉以在ΙΤ0基材上形成具有60 nm厚 度之電洞注入層。 接著，在真空氣相沉積設備之另一個小室中放入 33 94915 201114880 N，N’ -雙萘基）-N，n，一二笨基_4,4, _二胺（_)，並 且施加電流至小室以蒸發NPB，藉以在電洞注入層上形成 具有20 nm厚度之電洞傳輸層。 在形成電洞注入層和電洞傳輸層之後，如下所述於其 上形成電場發光層。將化合物83置入真空氣相沉積設備;乍 為主體，並將化合物Ε置入另一個小室作為擦雜劑。將此 兩種材料以不同速率蒸發，以使具有3〇nm厚度之電場發光 層（以主體為基礎計摻雜2至5wt%)氣相沉積於電洞傳輸層 上。Preparation of Compound 1 -1 2,7-dibromonaphthalene (20 g (g) '128.02 mmol (mmol)) was dissolved in 〇MF (200 ml (mL) ))in. Then, NBS (50.1 g, 281.65 mmol) was slowly added at room temperature. After stirring at room temperature for 24 hours, the organic solvent was distilled under reduced pressure. After adding distilled water, the mixture was extracted with EA to give Compound 1 (36 g, 114.64 mmol, 89.56 %). Preparation of Compound 1-2 Compound 1-1 (36 g, 114.64 mmol), phenylboronic acid (41. 9 g, 343.92 mmol), hydrazine (triphenylphosphine) Ι ε (tetrakis (triphenylphosphine) (Palladium) (Pd (PPh 〇 4, 6. 6 g, 5. 73 mmol), 3 M K2C 〇 3 (115 mL), toluene (500 mL), and ethanol (200 mL), and then stirred under reflux. After 6 hours of reaction and then cooled to room temperature, distilled water was added. After extraction with EA and drying with MgSCU, distillation under reduced pressure, followed by column separation to obtain compound 1-2 (29 g, 94.02 mmol, 82. 48%) Preparation of compound 1-3 KMn〇4 (74. 2 g, 470.13 mmol) was mixed with steamed water (70 mL) and mixed with 26 94915 201114880, then the ratio of ° was determined (400 mL) with compound 1 -2 (29 g) was added thereto. After heating to 130 2 C, KMn〇4 (20 g) was separated from distilled water (60 mL) and added 4 times for 30 minutes. After 5 hours, 400 mL of distilled water was added and The mixture was stirred under reflux for 12 hours. The reaction mixture was filtered while stirring under reduced pressure, then washed with distilled water, extracted with EA and dried over MgSCU, and then distilled under reduced pressure. Compound 1-3 (16 g, 43.43 mmol '46.20%) was obtained by column chromatography. Preparation of Compound 1-4 Compound 1-3 (16 g, 43.43 mmol) was dissolved in methanol (300 mL) Then, SOC12 was slowly added at room temperature. After stirring for 12 hours under reflux, distilled water was added, extracted with EA and dried with MgSCh, and then distilled under reduced pressure, followed by column separation to obtain compound 1- 4 (9 g, 22.70 mmol, 52.99%). Preparation of compound 1-5 Compound 4 (9 g, 22.70 mmol) was dissolved in THF (400 mL) and then brominated slowly at room temperature Magnesium hydride (53 mL, 158.91 _ 〇1, 3.0 Μ in diethyl ether). After stirring for 12 hours at 60 SC, distilled water was slowly added, extracted with EA and dried with MgS 4 and then evaporated. Distillation, followed by column separation to obtain compound 1-5 (5.6 g, 14.12 mmol, 62.21%). Preparation of compound 1-6 Compound 1-5 (5.6 g, 14.12 mmol), acetic acid (100 mL) and H3P〇4 (200 mL) were mixed and then stirred under reflux. After 10 hours, after cooling to room temperature, steaming water was added. After neutralizing with aqueous NaOH, 27 94915 201114880 was extracted with EA and dried with MgSO 4 , and then evaporated under reduced pressure, and then obtained by column chromatography to obtain compound 1-6 (2.5 g, 6.93 mmol, 49.11 %). Preparation of Compound 1-7 Compound 1-6 (2.5 g ' 6.93 mmol) was dissolved in THF (50 mL), then NBS (1·35 g, 7.62 mmol). After 12 hours of searching, the organic solvent was distilled under reduced pressure. The compound 1-7 (2.7 g, 6.14 mmol, 88.67%) was obtained by column chromatography. Preparation of Compound 1 Compound 1-7 (2.7 g ' 6. 14 mmol), 9-phenyl-10-indole boronic acid (2.19 g '7.33 mmol), hydrazine (triphenylphosphine) palladium ( Pd(PPh3)4, 〇. 35 g, 0. 30 mmol), 3 M aqueous K 2 CO 3 (6 mL), benzene (40 mL) and ethanol (15 mL) were mixed and then stirred under reflux. After 8 hours of reaction and cooling to room temperature, distilled water was added. After extracting with EA and drying with MgS 〇 4, it was distilled under reduced pressure, and then the compound hydrazine (2 4 g, 3.91 mmol, 63.78%) was obtained by column separation. Compounds 1 to 102 were prepared according to the procedure of Preparation Example i. The enthalpy_R&MS/FAB data of the organic electroluminescent compound thus produced are shown in Table 1. 94915 28 201114880 丨 Table 1 Compound Ή NMR (CDCls, 200 MHz) MS/FAB Measured value 1 (5 = 1.78 C12H, s), 7.1 (1H, m), 7.24 (2H, m), 7. 39- 7. 44(7H, m), 7. 51-7. 52(4H, m), 7. 61(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m) , 8. 09C2H, m) 612.80 612.28 2 ά = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 44(6H, m), 7. 55(2H , m), 7.6K3H, m), 7.9K4H, m), 7.95C1H, s), 7.99-8.09(5H, m), 8.42(1H, m), 8.55(1H, m) 662.86 662. 30 4 ( 5 = 1.78C12H, s), 2.34C3H, s), 7.1(1H, m), 7.24-7.44C12H, m), 7.61C2H, m), 7.9K4H, m), 7.95(1H, s), 7.99( 1H, m), 8.09(2H, m) 626. 83 626. 30 6 ^ = 1.78C12H, s), 7.1(1H, ra), 7. 24-7. 25(6H, n), 7.39-7.44( 7H, m), 7. 51-7. 52(4H, m), 7.61(2H, in), 7.9K4H, m), 7.95(1H, s), 7. 99(1H, in), 8. 09 (2H, m) 688. 90 688. 31 10 5 = 1.78(12H, s), 7(1H, m), 7.1(1H, m), 7. 24-7. 26(3H, m), 7. 39-7. 44(6H, m), 7. 51(1H, m), 7.6K2H, in), 7.91(4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H , m), 8.5(1H, m) 613.79 613.28 16 (5 = 1.78(12H, s), 7.1(1H, m), 7.24-7.3(4H, m), 7.39-7.4 4(8H, m), 7.61(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, in), 8.09(2H, m) 630. 79 630. 27 21 (5 = 1.78C12H, s), 7. 1(1H, in), 7.24(2H, in), 7.39-7.44(8H, m), 7.51(4H, m), 7.6K2H, m), 7.91(4H, m) , 7.95(1H, s), 7.99(1H, m), 8.09(2H, m), 8.28(4H, m) 767. 96 767. 33 25 5 = 1.78(12H, s), 7.1(1H, m) , 7. 24-7. 25(3H, m), 7.33-7.5C10H, m), 7.58-7.61(4H, m), 7. 69(1H, m), 7. 77(1H, m), 7 87-7. 94(6H, m), 7.95C1H, s), 7.99(1H, m), 8.09(2H, in), 8.55C1H, m) 777. 99 777. 34 31 δ = 1.78C12H, s ), 7.1(1H, m), 7.24(2H, in), 7.39-7.44(6H, m), 7.58-7.6K3H, m), 7.79-7.8C2H, m), 7.9-7.9K5H, m), 7.95 (1H, s), 7.96-7. 99(2H, m), 8.09-8. 1(4H, m), 736. 94 736.31 29 94915 201114880 8. 42(2H, m) 32 <5 = 1.78( 12H, s), 7. 1(1H, m), 7. 24-7. 33(5H, m), 7.4-7.5C7H, m), 7.61-7.63(3H, m), 7.9-7.94C5H, m ), 7.95(1H, s), 7.99(1H, m), 8. 09-8.12(3H, m), 8. 55(1H, m) 701.89 701.31 33 (5 = 1.78C12H, s), 7.1(1H , m), 7. 24-7. 25(6H, m), 7.39-7.52(13H, m), 7.61(2H, m), 7. 85(2H, m), 7.9K4H, m), 7.95( 1H, s), 7.99 (1 H, m), 8. 09(2H, m) 764. 99 764. 34 36 5 = 1.78(18H, s), 7.1-7.14C2H, m), 7. 24(2H, m), 7.39-7.44( 6H, m), 7.51-7.54(2H, m), 7.61(2H, m), 7.69(1H, m), 7.83(1H, m), 7. 91(4H, m), 7.95C1H, s), 7. 98-7. 99(2H, m), 8.09(3H, m), 8.15(1H, m), 8.52(1H, m) 779. 02 778. 36 40 5 = 1.78C12H, s), 7.1( 1H, m), 7. 24-7. 5(12H, m), 7.61-7.68(5H, m), 7.79(2H, m), 7.91-7.94C5H, m), 7.95(1H, s), 7.99 (1H, m), 8. 09-8.12(3H, m), 8. 55(1H, m) 777. 99 777. 34 41 (5 = 1.72C12H, s), 1.78(12Η, s), 7.1( 1H, m), 7. 24(3H, m), 7. 39-7. 44(7H, m), 7. 61-7. 63(4H, m), 7.69C1H, s), 7.77(2H, s), 7.77(0H, m), 7.91-7.93C5H, m), 7.95(1H, s), 7.99(1H, m), 8. 09(3H, m) 845.12 844. 41 45 5 = 1.72C6H, s), 1.78C12H, s), 7.1(1H, m), 7. 24(2H, m), 7. 33-7. 44(9H, m), 7. 61(2H, m), 7.71C1H, m), 7.9K4H, m), 7.95(1H, s), 7.97(1H, s), 7.99(1H, m), 8.09(2H, m), 8.78(1H, s), (H,) 729. 95 729. 34 47 5 = 1.78(12H, s), 6.97(2H, m), 7.1(1H, m), 7.16-7.24C8H, m), 7. 38(4H, m), 7. 44(2H , m), 7.61(2H, m), 7.88-7.9(4H, m), 7.95C1H, s), 7. 99(1H, m), 8. 09(2H, m) 733. 96 733. 28 54 5 = 1.72C6H, s), 1.78C12H, s), 6.55C1H, m), 6.61-6.63C3H, m ), 6. 73(1H, m), 6.81(1H, m), 7.02-7.1(3H, m), 7.2-7.24(4H, m), 7.36-7.44(7H, m), 7.6K3H, m) , 7.91(4H, m), 7.95(1H, s), 7.99C1H, m), 8.09(2H, m) 820. 07 819.39 30 94915 201114880 55 δ = 1.78C12H, s), 7.1(1Η, m), 7. 24-7. 25(6H, m), 7. 39-7. 44(6H, m), 7. 55(2H, m), 7. 61(3H, m), 7. 91(4H, m), 7. 95(1H, s), 7. 99-8. 09(5H, m), 8.42C1H, m), 8.55(1H, m) 738. 95 738. 33 56 5 = 1.78C12H, s ), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 48(8H, m), 7. 57-7. 61 (6H, m), 7.7-7.73C2H, m), 7.91-7.92(5H, m), 7.95(1H, s), 7.99-8C3H, m), 8.09(2H, m) 738. 95 738. 33 57 5 = 1.72(6H, s), 1.78C12H, s) , 7. 1(1H, m), 7. 24-7. 28(3H, m), 7. 38-7. 47(9H, m), 7. 55(1H, in), 7.61-7.63 (3H , m), 7.77(1H, m), 7. 85-7. 93(8H, m), 7.95C1H, s), 7. 99(1H, m), 8. 09(2H, m) 805. 06 804. 38 59 5 = 1.78(12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7.44(11H, m), 7.51-7. 52(4H, m), 7.61 (2H, m), 7.91(8H, m), 7.95(1H, s), 7.99C1H , m), 8.09(2H, m) 789.01 788. 34 60 <5 = 1.78(12H, s), 7.1(1H, m), 7. 24-7. 25(6H, in), 7.39-7.44C11H , m), 7.51-7.52(4H, m), 7.61(2H, m), 7.9K8H, m), 7.95(1H, s), 7. 99(1H, in), 8. 09(2H, m) 865.11 864. 38 62 5 = 1.78C12H, s), 7. 1(1H, m), 7.24(2H, m), 7.39-7.44(7H, m), 7.5K2H, in), 7.61(4H, m) , 7.79(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99C1H, m), 8.09(2H, m), 8.42(2H, m), 8.5K2H, in) 738. 95 738 33 63 <5 = 1.78(12H, s), 6. 63(4H, m), 6. 69(2H, m), 6.81C2H, m), 7.1(1H, m), 7.2-7.24(6H , m), 7.39-7.44(6H, m), 7.54(2H, m), 7.61(2H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m), 8. 09 (2H, m) 780.01 799. 36 64 δ = 1.78(12H, s), 7. 1-7.11 (7H, m), 7.24-7.44(21H, m), 7.61(2H, m), 7.9K4H, m ), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m) 855.11 855.39 65 5 = 1.78(12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 44C6H, m), 7. 55(2H, m), 7. 61-7. 64(3H, ii), 7.74-7.84(6H, m), 7.9K4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m) 716.91 716.31 31 94915 201114880 70 (5 = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7. 39-7. 44C6H, m), 7. 61(2H, m), 7.91C4H, m), 7.95(1H, s), 7.99(1H, m), 8.09(2H, m) 617.83 617.31 75 5 = 1.78(12H, s), 2.34(3H, s), 7. 1(1H, m), 7. 24(2H, m), 7. 39-7. 44(7H, m), 7.51-7. 52(4H, m), 7.6K1H, m), 7.9K4H, m), 7.95(1H, s), 7. 97-7. 99(2H, m), 8. 09(1H, m) 626.83 626.30 77 5 = 1.78C12H, s), 2.34C6H, s), 7. 1(1H, m), 7. 24(2H, m), 7. 39-7. 41 (7H, m), 7. 51 -7. 52(4H, m), 7.9K4H, m), 7.95(1H, s), 7. 97-7. 99(3H, m) 640. 85 640.31 80 5 = 1.78(12H, s), 7 .1(1H, m), 7.24(1H, m), 7. 39-7. 44(6H, m), 7. 51-7. 52(4H, m), 7.6K1H, m), 7.69(1H , m), 7.86-7.91(5H, m), 7.95(1H, s), 7.99(1H, m), 8.09(1H, m), 8.27(1H, m) 637.81 637. 28 82 δ = 1.78C12H, s), 7.1(1H, m), 7. 39-7. 41(7H, m), 7. 51-7.52(12H, m), 7. 69(2H, m), 7. 83(2H, m ), 7.91(4H, m), 7.95(1H, s), 7.99(1H, m), 8.15C2H, m) 764. 99 764. 34 83 δ = 1.78C12H, s), 7. 1(1H, m ), 7.24(2H, m), 7. 39-7. 44(6H, m), 7. 51-7. 52(8H, m), 7.61C3H, m), 7.9K2H, m), 7.95(1H , s), 7.97-7.99(2H, m), 8.09-8.13(3H, m) 688. 90 688.31 86 (5 = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7.41-7.44(5H, m), 7.51-7.52(12H, m), 7.6K4H, m), 7.95C1H, s), 7.97-7.99(3H, m), 8.09-8.13(4H, m) 764. 99 764. 34 87 5 = 7.39-7.41 (5H, m), 7. 5-7. 52(8H, m), 7.58( 1H, m), 7.8(1H, m), 7.9K4H, m), 7.98C2H, m), 8.08(1H, s), 8.45(2H, m) 592. 77 592.13 93 5 = 7.32-7.4K7H, m ), 7.5-7.52(6H, m), 7. 59(1H, m), 7. 66(2H, m), 7. 89-7. 91(5H, tn), 7.98C1H, m), 8.08( 1H, s), 8.45(1H, m) 576. 70 576.15 98 5 = 1.78(12H, s), 2.45(6H, s), 7. 1(1H, m), 7. 24-7. 25(4H , m), 7.41-7.44(3H, m), 7. 51-7. 52(4H, m), 7. 61(2H, m), 7. 7(2H, m), 7.85C2H, m), 7.95(1H, s), 7.99C1H, m), 8.09C2H, m) 640. 85 640. 31 32 94915 201114880 99 5 = 0.9(12H, m), 1.9K8H, m), 7.1(1H, m), 7. 24(2H, m), 7. 39-7. 44(7H, m), 7. 51-7. 52(4H, m), 7.61(2H, m), 7.91(4H, m), 7.95 (1H, s), 7. 99(1H, m), 8. 09(2H, m) 668.91 668. 34 100 δ = 1.84C12H, s), 7.1(1H, m), 7. 39-7. 41 (5H, m), 7.51-7.58C10H, m), 7. 91(4H, m), 7. 95(1H, s), 7.97-8.01(5H, m), 8.28(2H, m) 712.92 712.31 101 5 = 1.78C12H, s), 7.1(1H, m), 7.24(2H, m), 7.39-7.44C6H, m), 7. 51-7. 52(4H, m), 7. 61(2H, m), 7.82-7.91 (5H, m), 7.95(1H, s), 7.99(1H, b), 8. 09-8.12(3H, m), 8. 93(1H, m) 662. 86 662. 30 102 5 = 1.78C24H, s) , 7.1(2H, m), 7.24(4H, m), 7.39-7.44C8H, m), 7.61(4H, m), 7.9K4H, m), 7. 95C2H, s), 7.99C2H, m), 8.09 (4H, m) 895.18 894. 42 [Example 1] Manufacture of an OLED device using the organic electroluminescent compound of the present invention An OLED device was produced using the organic electroluminescent compound according to the present invention. First, a transparent electrode ΙΤ0 film obtained from OLED glass (manufactured by Samsung Corning) was subjected to ultrasonic cleaning with trichloroethylene, acetone, ethanol, and distilled water in that order, and stored in isopropyl alcohol for use. Next, the ΙΤ0 substrate is placed in a substrate holder of a vacuum vapor deposition apparatus, and 4,4',4"-parameter (N,N-(2-naphthyl)-phenylamino)triphenyl The amine (2-TNATA) is placed in one of the cells of the vacuum vapor deposition apparatus, and then ventilated to a vacuum in the chamber to 1 (ΓrTorr). Then, a current is applied to the chamber to evaporate 2-TNATA. A hole injection layer having a thickness of 60 nm is formed on the ΙΤ0 substrate. Next, in another chamber of the vacuum vapor deposition apparatus, 33 94915 201114880 N, N'-bisnaphthyl)-N, n, one or two is placed. Stinking _4,4, _diamine (_), and applying a current to the chamber to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Forming a hole injection layer and a hole After transporting the layer, an electroluminescent layer is formed thereon as follows. Compound 83 is placed in a vacuum vapor deposition apparatus; ruthenium is the main body, and the compound ruthenium is placed in another chamber as a rubbing agent. Evaporation at different rates to vapor-deposit an electroluminescent layer (2 to 5 wt% doped on a bulk basis) with a thickness of 3 〇 nm Hole transport layer.

化合物83 化合物E 之後，氣相沉積具有20 nm厚度之參（8_羥基喹啉）鋁 (III)(Alq)作為電子傳輸層。接下來，氣相沉積具有j至 2 nm厚度之8-羥基喹啉鋰quin〇iate，LiQ)作 為電子注入層。使用另一個真空氣相沉積設備形成具有 150 nm厚度之鋁（A1)陰極以製造〇LED。 OLED中所使用的各化合物係在} 〇-6t〇rr下藉由真空昇 華純化者。 [實施例2]使用本發明之有機電場發光化合物之〇LED裝 置之製造 根據實施例1的步驟製造了 〇LED裝置，不同的是用 34 94915 201114880 化合物3及化合物A取代電場發光層中的化合物83及化合 物E 〇After compound 83 compound E, ginseng (8-hydroxyquinoline)aluminum (III) (Alq) having a thickness of 20 nm was vapor-deposited as an electron transport layer. Next, lithium 8-hydroxyquinolate quin〇iate (LiQ) having a thickness of j to 2 nm was deposited as an electron injecting layer. An aluminum (A1) cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to fabricate a ruthenium LED. Each compound used in the OLED was purified by vacuum sublimation under 〇-6t〇rr. [Example 2] Production of a ruthenium LED device using the organic electroluminescent compound of the present invention A ruthenium LED device was produced according to the procedure of Example 1, except that the compound in the electroluminescent layer was replaced by Compound 34 and Compound A of 34 94915 201114880 83 and compound E 〇

化合物3 化合物ACompound 3 Compound A

[比較例1]使用現存的電場發光材料之0LED裝置之製造 根據實施例1的步驟製造了 0LED裝置，不同的是將 二萘基蒽（DM)放入真空氣相沉積設備中作為主體材料取 代本發明之化合物。 [比較例2]使用現存的電場發光材料之0LED裝置之製造。 根據實施例2的步驟製造了 0LED裝置，不同的是將 DNA放入真空氣相沉積設備中作為主體材料取代本發明之 化合物。 於1，000燭光/平方米（cd/m2)測量實施例1與2以及 比較例1與2中製造之OLED裝置的功率效率。其結果列於 表2之中。 35 94915 201114880 表2[Comparative Example 1] Manufacture of an OLED device using an existing electric field luminescent material An OLED device was fabricated according to the procedure of Example 1, except that dinaphthyl fluorene (DM) was placed in a vacuum vapor deposition apparatus as a host material. A compound of the invention. [Comparative Example 2] Production of an OLED device using an existing electric field luminescent material. An OLED device was fabricated according to the procedure of Example 2, except that the DNA was placed in a vacuum vapor deposition apparatus as a host material in place of the compound of the present invention. The power efficiencies of the OLED devices manufactured in Examples 1 and 2 and Comparative Examples 1 and 2 were measured at 1,000 candelas per square meter (cd/m2). The results are shown in Table 2. 35 94915 201114880 Table 2

從表2可見’當使用於綠色或 φπ± ± 1 ^ 次藍色發射電場發光裝置 中時’相較於比較例1與2，本 + 明之有機電場發来化人 物提供經改善功率效率，同時也维 ° 色純度。 維持了可相比擬或較佳的 【圖式簡單說明】 〇*、 【主要元件符號說明】 益 * »»> 94915 36It can be seen from Table 2 that 'when used in green or φπ± ± 1 ^ times blue emission electric field illuminating device' compared to Comparative Examples 1 and 2, the organic electric field of the present invention provides improved power efficiency while Also the color purity. Maintain comparable or better [Simplified illustration] 〇*, [Key component symbol description] Benefit * »»> 94915 36

Claims (1)

201114880 七、申請專利範圍： • 丨.一種有機電場發光化合物，係由化學式（1)所示：201114880 VII. Patent application scope: • 丨 An organic electroluminescent compound, represented by chemical formula (1): 至Ris獨立地表示1、氛、鹵素、經取代或未經 取代之（C1-C30)院基、經取代或未經取代之（C6-C30) 芳基、與一個或多個經取代或未經取代之（C3-C30)環院 基稠合之經取代或未經取代之（C6_C30)芳基、經取代或 未經取代之（C3-C30)雜芳基、經取代或未經取代之5 至7元雜環烧基、與一個或多個經取代或未經取代之芳 玉衣稠s之5至7元雜壤烧基、經取代或未經取代之 (C3-C3 0)環烧基、與一個或多個經取代或未經取代之芳 環稠合之（C3-C30)環烷基、氰基、NR21R22、BR23R24、 PR25R26、P(=〇)R27R28[其中’心至R28獨立地表示經取代 或未經取代之（Cl-C3〇)烷基、經取代或未經取代之 (C6-C30)芳基’或經取代或未經取代之（C3_C3〇)雜芳 基]、RaRbRcSi-[其中，Ra、Rb、獨立地表示經取代或 未經取代之（C1-C30)炫基，或經取代或未經取代之 (C6_C30)芳基]、經取代或未經取代之（C6-C30)芳基 (C卜C30)烷基、RdY一[其中’ γ表示s或〇,且Rd表示經 94915 37 201114880 取代或未絲代之（G卜C3G)絲或經取代或未經取代 之（C6_C3〇)芳基]、經取代或未經取代之（C2-C30)烯 基、經取代或未經取代2(C2-C3〇)炔基、Rec(=〇)_[其 中’ 表示經取代或未經取代之（C1_⑽）絲、經取代 或未經取代之（C1-C30)烧氧基、經取代或未經取代之 (C6-C30)芳基’或經取代或未經取代之（C6C3〇)芳氧 基]、R (：(=0)〇-[其巾，Rf表示經取代或未經取代之 (C1-C30)烷基、經取代或未經取代之（cl_C3〇)烷氧基、 經取代絲轉代之⑽_G3G)綠，或録代或未經取To Ris independently denotes 1, aryl, halogen, substituted or unsubstituted (C1-C30), substituted or unsubstituted (C6-C30) aryl, with one or more substituted or not Substituted (C3-C30) ring-substituted fused or unsubstituted (C6_C30) aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted 5 to 7 membered heterocycloalkyl, 5 to 7 membered heterobasin, substituted or unsubstituted (C3-C3 0) ring with one or more substituted or unsubstituted aromatic sap An alkyl group fused to one or more substituted or unsubstituted aromatic rings (C3-C30) cycloalkyl, cyano, NR21R22, BR23R24, PR25R26, P(=〇)R27R28 [wherein heart to R28 Independently represented by a substituted or unsubstituted (Cl-C3〇)alkyl group, a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (C3_C3〇)heteroaryl group] , RaRbRcSi-[wherein, Ra, Rb, independently represent a substituted or unsubstituted (C1-C30) leukoyl group, or a substituted or unsubstituted (C6_C30) aryl group], substituted or unsubstituted (C6-C30) aryl (C C30) alkyl, RdY-[wherein γ represents s or fluorene, and Rd represents a substituted or unsubstituted (Gb C3G) filament or a substituted or unsubstituted (C6_C3〇) aryl group by 94915 37 201114880] , substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted 2(C2-C3〇)alkynyl, Rec(=〇)_[where ' represents 'substituted or unsubstituted ( C1_(10)) silk, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) aryl ' or substituted or unsubstituted (C6C3 fluorene) aryloxy ], R (:(=0)〇-[其巾, Rf represents substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (cl_C3〇) alkoxy, substituted silk (10)_G3G) is replaced by green, or recorded or not taken 或羥基，或者，它們可藉由具有或不具有稠 合環之（C3-C30)伸烷基或（C3—C30)伸烯基鍵聯至相鄰 取代基以形成脂環、或單環或多環之芳環； A、β以及W獨立地表示_(CR51R52)m-、 ~(R5i)C=C(R52)- > -N(R53)- ^ -p(r56)-、一p(=0)(R57)_、h Rsi 至 Rm » k e u ' -S-' -0-> -Si(R54)(R55)_ , -C(=0)-或-B(R58)-，其中， 至R58及Rei至Reg相同於％至r18 ; 該雜環院基及雜芳基可含一個或多個選自b、n、 s、P(=0)、Si及P之雜原子；以及 m表示1或2之整數。 94915 38 201114880 t .2.如中請專補㈣1項所述之有機電場發光化合物，立 中：匕至R18、R21至R28、r51至R58及Rei至R63定義中的 經取代或未經取代，，之取代基係獨立地更進一步經 —個❹個選自m素、具有或不具鹵素取代基 = (Π-_烧基、⑽-⑽）芳基、具有或不具（c6、c3〇) 方基取代基之⑹-⑽）雜芳基、5至7元雜環烧基、斑 :個或多個芳環稠合之5至7it雜魏基、⑹_咖、 %烧基、與-個或多個芳環_合之⑽—⑽）環院基、三 (C1-C30)院基石夕烧基、二（C1_C3())燒基（c6c3〇)芳基石夕 燒基、二（C6-C30)芳基石浅基、⑽_C3〇)稀基、（C2—C3〇) 炔基、氰基、咔唑基、nr31r32、br33r34、PR35R36、p(=0)R37R38 [其中，心至R38獨立地表示（C1—C30)烷基、（C6-C30) 芳基或（C3-C30)雜芳基]、（C6-C30)芳基（C1-C30)烷 基、（C1-C30)烷基（C6-C30)芳基、（C1-C30)烷氧基、 (C1-C30)烷基硫基、（C6-C30)芳氧基、（C6-C30)芳硫 基、（C1-C30)烷氧基羰基、（C1-C30)烷基羰基、（C6-C30) 芳基羰基、（C6-C30)芳氧基羰基、（C1-C30)烷氧基羰氧 基、（C1-C30)烷基羰氧基、（C6-C30)芳基羰氧基、 (C6-C30)方氧基幾氧基、緩基、硝基以及經基組成之群 組之取代基取代；或者，其係鍵聯至相鄰取代基以形成 壤。 3·—種有機電場發光裝置，包含如申請專利範圍第1或2 項所述之有機電場發光化合物。 4·如申請專利範圍第3項所述之有機電場發光裝置，其包 39 94915 201114880 含第一電極；第二電極；以及一層或多層有機層，該有 機層係設於該第一電極以及該第二電極之間，其中，該 有機層包含一個或多個如申請專利範圍第丨或2項所述 之有機電場發光化合物及一個或多個由化學式（2)至（4) 所示之摻雜劑：Or a hydroxy group, or they may be bonded to an adjacent substituent by a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form an alicyclic ring, or a monocyclic ring or Polycyclic aromatic ring; A, β and W independently represent _(CR51R52)m-, ~(R5i)C=C(R52)- > -N(R53)- ^ -p(r56)-, a p (=0)(R57)_, h Rsi to Rm » keu ' -S-' -0-> -Si(R54)(R55)_ , -C(=0)- or -B(R58)-, Wherein, to R58 and Rei to Reg are the same as % to r18; the heterocyclic and heteroaryl groups may contain one or more heteroatoms selected from the group consisting of b, n, s, P(=0), Si and P; And m represents an integer of 1 or 2. 94915 38 201114880 t .2. If the organic electroluminescent compound described in (4) (1) is used, the intermediate: 匕 to R18, R21 to R28, r51 to R58 and the substituted or unsubstituted in the definition of Rei to R63, The substituents are independently further selected from the group consisting of m, with or without a halogen substituent = (Π-_alkyl, (10)-(10)) aryl, with or without (c6, c3〇) a (6)-(10))heteroaryl group of a substituent, a 5- to 7-membered heterocycloalkyl group, a plaque: one or more aromatic rings fused by 5 to 7 is a hetero- Wei group, (6)-coffee, a % alkyl group, and a Or a plurality of aromatic rings _ (10) - (10) ring ring base, three (C1-C30) yard base stone base, two (C1_C3 ()) base (c6c3 〇) aryl rock smelting base, two (C6- C30) aryl fluoride, (10) _C3 〇), (C2-C3 〇) alkynyl, cyano, carbazolyl, nr31r32, br33r34, PR35R36, p(=0)R37R38 [wherein, heart to R38 are independently represented (C1-C30)alkyl, (C6-C30) aryl or (C3-C30)heteroaryl], (C6-C30)aryl(C1-C30)alkyl, (C1-C30)alkyl (C6 -C30) aryl, (C1-C30) alkoxy, (C1-C30)alkylthio, (C6-C30) aryloxy, C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl, (C1-C30 Alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)oxyloxy, sulfhydryl, nitro and thiol Substituents of the constituent groups are substituted; or, they are bonded to adjacent substituents to form a soil. An organic electric field illuminating device comprising the organic electroluminescent compound according to claim 1 or 2. 4. The organic electric field light-emitting device according to claim 3, wherein the package 39 94915 201114880 comprises a first electrode; a second electrode; and one or more organic layers, the organic layer being disposed on the first electrode and the Between the second electrodes, wherein the organic layer comprises one or more organic electroluminescent compounds as described in claim 2 or 2 and one or more of the blends represented by the chemical formulas (2) to (4) Miscellaneous: (2) (3) Aril及An2獨立地表示經取代或未經取代之 (C1-C30)烷基、經取代或未經取代之（C6-C30)芳基、經 取代或未經取代之（C4-C30)雜芳基、經取代或未經取代 之（C6-C30)芳基胺基、（C1-C30)烧基胺基、經取代或未 經取代之5至7元雜環烷基、與一個或多個經取代或未 經取代之芳環稠合之5至7元雜環烷基、經取代或未經 取代之（C3-C30)環烧基’或與一個或多個經取代或未經 取代之芳環稠合之（C3-C30)環烷基，或者，Aril及Ari2 藉由具有或不具稠合環之（C3-C30)伸烷基或（C3-C30) 伸烯基鍵聯以形成脂環、或單環或多環之芳環； 於c為1時’ Aru表示經取代或未經取代之 芳基、經取代或未經取代2(C4_C3〇)雜芳基或選自下列 94915 40 201114880 結構之取代基：(2) (3) Aril and An2 independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted ( C4-C30)heteroaryl, substituted or unsubstituted (C6-C30)arylamino, (C1-C30)alkylamino, substituted or unsubstituted 5 to 7-membered heterocycloalkyl a 5 to 7 membered heterocycloalkyl group substituted with one or more substituted or unsubstituted aromatic rings, substituted or unsubstituted (C3-C30)cycloalkyl group' or with one or more a substituted or unsubstituted aromatic ring fused (C3-C30) cycloalkyl, or Aril and Ari2 (C3-C30) alkyl or (C3-C30) alkylene with or without a fused ring The group is bonded to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when c is 1, 'Aru represents a substituted or unsubstituted aryl group, a substituted or unsubstituted 2(C4_C3〇)heteroaryl group. Or a substituent selected from the following 94915 40 201114880 structure: 於c為2時，An3表示經取代或未經取代之（C6-C30) 伸芳基、經取代或未經取代之（C4-C30)伸雜芳基或選自 下列結構之取代基：When c is 2, An3 represents a substituted or unsubstituted (C6-C30) extended aryl group, a substituted or unsubstituted (C4-C30) heteroaryl group or a substituent selected from the following structures: Aru及Aris獨立地表示經取代或未經取代之 (C6-C30)伸芳基或經取代或未經取代之（C4-C30)伸雜 芳基； R2〇i至R2。3獨立地表示氫、氘、經取代或未經取代 之（C1-C30)烷基，或經取代或未經取代之（C6-C30)芳 基； d表示從1至4之整數； e表示0或1之整數；以及Aru and Aris independently represent substituted or unsubstituted (C6-C30) extended aryl or substituted or unsubstituted (C4-C30) heteroaryl; R2〇i to R2. 3 independently represent hydrogen , hydrazine, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; d represents an integer from 1 to 4; e represents an integer of 0 or 1. ;as well as (4) 其中， Rm至Rm獨立地表示氫、氘、鹵素、經取代或未 經取代之（C1-C30)烷基、經取代或未經取代之（C6-C30) 芳基、經取代或未經取代之（C3-C30)雜芳基、經取代或 41 94915 201114880 未經取代之5至7-元雜環烷基、與一個或多個經取代 或未經取代之芳環稠合之5至7元雜環烷基、經取代或 未經取代之（C3-C30)環烧基、與一個或多個經取代或未 經取代之芳環稠合之（C3-C30)環烷基、氰基、NR3QIR3()2、 BR3〇3R3〇4、PRmfU、P(=〇)r307r3()8 [其中，r301 至 R_獨立 地表示經取代或未經取代之（C1—C30)烷基、經取代或未 經取代之（C6-C30)芳基’或經取代或未經取代之 (C3-C30)雜芳基]、經取代或未經取代之三（cl_C3〇)烷 基矽烷基、經取代或未經取代之二（q_C3〇)烷基 (C6-C30)芳基矽烷基'經取代或未經取代之三（C6C3〇) 芳基矽烷基、經取代或未經取代之（C6_C3〇)芳基 (C1-C30)烷基、經取代或未經取代之（cl_C3〇)烷氧基、 經取代或未經取代之（C1-C30)烷基硫基、經取代或未經 取代之（C6-C30)芳氧基、經取代或未經取代之（C6_C3〇) 芳硫基、經取代或未經取代之（n_C3〇)烷氧基羰基、經 取代或未經取代之（C1-C30)烷基羰基、經取代或未經取 代之（C6-C30)芳基羰基、經取代或未經取代之（C2_c3〇) 烯基、經取代或未經取代2(C2_C3〇)炔基、經取代或未 經取代之（C6-C30)芳氧基縣、經取代或未經取代之 (Π-G⑹絲絲氧基、錄代或未絲代之⑹-㈣ 院基幾氧基、經取代或未經取代之（C6_C3〇)芳基幾氧 基、經取代或未經取代之（C6_C3〇)芳氧基幾氧基、缓 基、石肖基或經基；或者，它們各自可藉由具有或不具有 稠合環之（C3-C30)伸烧基或⑽―⑽伸婦基鍵聯至相 94915 42 201114880 t 鄰取代基以形成脂環、或單環或多環之芳環。 ' 5.如申請專利範圍第4項所述之有機電場發光裝置，其 ' 中，該有機層包含一種或多種選自芳基胺化合物以及苯 乙烯基芳基胺化合物組成之群組之化合物。 6. 如申請專利範圍第4項所述之有機電場發光裝置，其 中，該有機層更進一步包括一種或多種選自第1族之有 機金屬、第2族、第4週期與第5週期之過渡金屬、鑭 系金屬與d-過渡元素組成之群組之金屬或錯化物。 7. 如申請專利範圍第4項所述之有機電場發光裝置，其 中，該有機層包含電場發光層以及電荷產生層。 8. 如申請專利範圍第4項所述之有機電場發光裝置，其發 白光有機電場發光裝置，其中，該有機層包含一層或多 層同時發射紅、綠或藍光之有機電場發光層。 43 94915 201114880 四、 指定代表圖：本案無圖式 (一) 本案指定代表圖為：第（）圖。 (二) 本代表圖之元件符號簡單說明： 五、 本案若有化學式時，請揭示最能顯示發明特徵的化學式：(4) wherein Rm to Rm independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or Unsubstituted (C3-C30)heteroaryl, substituted or 41 94915 201114880 unsubstituted 5 to 7-membered heterocycloalkyl, fused to one or more substituted or unsubstituted aromatic rings 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, (C3-C30) cycloalkyl fused to one or more substituted or unsubstituted aromatic rings , cyano, NR3QIR3()2, BR3〇3R3〇4, PRmfU, P(=〇)r307r3()8 [wherein, r301 to R_ independently represent a substituted or unsubstituted (C1-C30) alkyl group. , substituted or unsubstituted (C6-C30) aryl ' or substituted or unsubstituted (C3-C30)heteroaryl], substituted or unsubstituted tris(cl_C3〇)alkyl fluorenyl , substituted or unsubstituted bis(q_C3〇)alkyl (C6-C30) arylalkylalkyl' substituted or unsubstituted tris(C6C3〇)arylalkyl, substituted or unsubstituted ( C6_C3〇) aryl (C1-C30) alkyl, Substituted or unsubstituted (cl_C3〇)alkoxy, substituted or unsubstituted (C1-C30)alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or substituted Unsubstituted (C6_C3〇) arylthio, substituted or unsubstituted (n-C3〇)alkoxycarbonyl, substituted or unsubstituted (C1-C30)alkylcarbonyl, substituted or unsubstituted (C6-C30) arylcarbonyl, substituted or unsubstituted (C2_c3〇) alkenyl, substituted or unsubstituted 2(C2_C3〇)alkynyl, substituted or unsubstituted (C6-C30) Aryloxy, substituted or unsubstituted (Π-G(6) silky, substituted or unsubstituted (6)-(tetra) benzyloxy, substituted or unsubstituted (C6_C3〇) aryl a oxy group, a substituted or unsubstituted (C6_C3 fluorene) aryloxy oxyoxy group, a slow group, a schlossyl group or a thiol group; or, each of them may be (C3-C30) with or without a fused ring. Stretching base or (10) - (10) stretching base to phase 94915 42 201114880 t ortho substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring. ' 5. As described in claim 4 An organic electric field light-emitting device, wherein the organic layer comprises one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds. 6. Organic as described in claim 4 An electric field illuminating device, wherein the organic layer further comprises one or more groups selected from the group consisting of organometallics of Group 1, Group 2, transition metals of Period 4 and Cycle 5, groups of lanthanide metals and d-transition elements Group of metals or complexes. 7. The organic electroluminescent device of claim 4, wherein the organic layer comprises an electric field luminescent layer and a charge generating layer. 8. The organic electroluminescent device of claim 4, wherein the organic layer comprises one or more organic light-emitting layers that simultaneously emit red, green or blue light. 43 94915 201114880 IV. Designated representative map: There is no schema in this case (1) The representative representative map of this case is: (). (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 2 949152 94915
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