TW201109420A - 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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TW201109420A
TW201109420A TW099120051A TW99120051A TW201109420A TW 201109420 A TW201109420 A TW 201109420A TW 099120051 A TW099120051 A TW 099120051A TW 99120051 A TW99120051 A TW 99120051A TW 201109420 A TW201109420 A TW 201109420A
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aryl
alkyl
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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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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

201109420 六、發明說明： 【發明所屬之技術領域】 本發明係有關-種新穎有機電場發光化合物及包括該 化合物之有機電場發光裝置。依據本發明之有機電場發光 化合物係以化學式（1)表示之： r2201109420 VI. 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 comprising the same. The organic electroluminescent compound according to the present invention is represented by the chemical formula (1): r2

【先前技術】 ，，貝示褽置中，電場發光（electroluminescent, EL)裝 置的優點在於其作為自發光顯示裝置係提供廣視角，優越 對比及快速響應速率。於1987年，伊士曼柯達公司首先發 ^出一種使用低分子量芳錢二胺及⑽合物作為形成電 暴發光層之物貝之有機EL裝置[細?/. /¾% Zeii. 51，913 “在有機EL裝置中，當對形成於電子注入電極（陰極 與電洞注入電極（陽極）間之有機層施加電荷時，使電子/ 電洞配對，而於電子-電洞對熄滅時發出光。與電漿颟示— 面板或無機EL顯示器相較下，有機El裝置的優點在於、 可在撓性透明基板如塑膠上形成，故可以相對較低的電j (10伏特（V)或更低）操作之，消耗較低的電能，且提供^ 201109420 異的顏色。此外，有機EL裝置由於可呈現綠色 色而以作為下一代全彩顯示裝置受到注目。 _ 及红 在有機EL裝置中’決定其性能包含發 命之最重要因素為電場發光材料1場發料:壽 求包含固態時之高電場發光量子產率，高電子:要 ^真空沉積期間之抗分解性’形成均勻膜之能力 -般而言，有機EL襄置通常具有陽極/電 ⑽)/電洞傳送層狐)/發光材料層（亂)/電子= (ETLV電子注人層（EIL)/陰極之組構。可生產發出^ =紅色光之有機電場發吻，視如何形成發;材料 = = = =分為主體材料與摻雜 場發光層會提供優_ EL製傷電 長工作壽命之有機EL裝置來，發展具有高效率及 思及中至大尺寸獅^戶^為刻不容緩的任務。尤其， 發展比时的電場發光材料優越度’迫切需要 對綠色螢光材料而言，係使 線f㈣物（綱d =)π) 喹吖啶酮（化合物e)，DPlY>a_ A t545T), 濃度為數個%至數十%。雖;等作為摻雜劑’摻雜 業化的初始發光效率，電場發光材料具備可商 於哥命問題，使其難以使用於高解由 94916 4 201109420[Prior Art] In the present invention, an electroluminescent (EL) device has an advantage in that it provides a wide viewing angle, superior contrast, and fast response rate as a self-luminous display device. In 1987, Eastman Kodak Company first developed an organic EL device using a low molecular weight aromatic diamine and a (10) compound as an electron beam luminescent layer [fine?/. /3⁄4% Zeii. 51, 913 "In an organic EL device, when an electric charge is applied to an organic layer formed between an electron injecting electrode (cathode and a hole injecting electrode (anode)), electrons/holes are paired, and when the electron-hole pair is extinguished Light. Compared with plasma display - panel or inorganic EL display, the advantages of the organic EL device are that it can be formed on a flexible transparent substrate such as plastic, so it can be relatively low power (10 volts (V) or Lower) operation consumes lower power and provides different colors for the 201109420. In addition, the organic EL device attracts attention as a next-generation full-color display device because it can be green. _ and red in the organic EL device 'The most important factor determining the performance of the life is the field emission of the electric field luminescent material: the high electric field luminescence quantum yield when the solid state is contained, and the high electron: the anti-decomposition during vacuum deposition to form a uniform film Ability - in general The organic EL device usually has an anode/electric (10)/hole transport layer fox)/luminescent material layer (chaotic)/electron=(ETLV electronic injection layer (EIL)/cathode structure. It can produce ^=red light The organic electric field kisses, depending on how the hair is formed; the material = = = = is divided into the main material and the doped field luminescent layer will provide an excellent EL EL working life of the organic EL device, the development of high efficiency and thinking The medium to large size lion ^ household ^ is an urgent task. In particular, the development of the ratio of the electric field luminescent material superiority 'emergency need for the green fluorescent material, the line f (four) thing (class d =) π) quinacridine Ketone (Compound e), DPlY>a_ A t545T), the concentration is several % to tens of %. Although; as the initial luminous efficiency of the dopant 'doping industry', the electric field luminescent material has a problem of sinister life, Make it difficult to use in high solutions by 94916 4 201109420

因此，需要發展能夠提供令人滿意之工作壽命的0LED裝 置、較佳安定性及優異性能的主體材料。 【發明内容】 技術問題 因此本發明之目的係提供一種具有較既有材料更加改 良之發光效率，裝置工作壽命且具備具有適當色座標之優 越骨架的有機電場發光化合物，以解決前述問題。本發明 之另一目的係提供一種使用此有機電場發光化合物作為電 場發光材料之有機電場發光裝置。 技術解決方案 就總態樣而言，本發明係提供一種化學式（1)所示之有 機電場發光化合物及包含該化合物之有機電場發光裝置。 因具備優越的發光效率及優異的壽命性質，使得依據本發 明之有機電場發光化合物可用於製造具有非常優越工作壽 命的0LED裝置。Therefore, there is a need to develop a host material which is capable of providing a satisfactory operational life of an OLED device, better stability, and superior performance. Disclosure of Invention Technical Problem Therefore, an object of the present invention is to provide an organic electroluminescent compound having an improved luminous efficiency, a working life of a device, and an excellent skeleton having an appropriate color coordinate to solve the aforementioned problems. Another object of the present invention is to provide an organic electric field light-emitting device using the organic electroluminescent compound as an electric field luminescent material. Technical Solution In its entirety, the present invention provides an organic electroluminescent compound of the formula (1) and an organic electric field illuminating device comprising the same. The organic electroluminescent compound according to the present invention can be used to manufacture an OLED device having a very superior working life due to its superior luminous efficiency and excellent lifetime properties.

5 94916 201109420 式中 1至_立表示氫U素、經取代或未經取代之 (C卜C3m基、錄代絲經取代之（G6_G3Q)芳基、與一 個或多個錄代或未經取代之（G3_⑽）敎㈣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_員雜環烷 基、與一個或多個經取代或未經取代之芳香環稠合之5一至 7-員雜垓烷基、經取代或未經取代之（C3_C3〇)環烷基、與 一個或多個經取代或未經取代之芳香環稠合之（C3_C3〇)環 烷基、氰基、NRhR12、BR13R14、PR15R16、P(=〇)Ri7Ri8[式中 Rn 至Ru獨立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（C3—C3 〇) 雜芳基]、RaRbReSi-[式中Ra、鲈及rc獨立表示經取代或未 經取代之（C1-C30)烧基或者經取代或未經取代之（c6_c3〇) 芳基]、經取代或未經取代之（C6-C30)芳基（C卜C3〇)烷基、 RdY-[式中Y表示S或0，及Rd表示經取代或未經取代之 (C卜C30)烷基或者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、經取代或未經取代之 CC2-C30)炔基、 R235 94916 201109420 wherein 1 to _ stand for hydrogen U, substituted or unsubstituted (C a C3m group, substituted silk substituted (G6_G3Q) aryl, with one or more recorded or unsubstituted (C3_(10)) 敎(d) substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30)heteroaryl' substituted or unsubstituted 5_ to 7 a heterocycloalkyl group, a 5- to 7-membered heteroalkyl group fused to one or more substituted or unsubstituted aromatic rings, a substituted or unsubstituted (C3_C3 fluorene) cycloalkyl group, and One or more substituted or unsubstituted aromatic rings fused (C3_C3〇)cycloalkyl, cyano, NRhR12, BR13R14, PR15R16, P(=〇)Ri7Ri8 [wherein Rn to Ru independently represent substituted or Unsubstituted (C1_C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C3 〇) heteroaryl], RaRbReSi- [in the formula, Ra,鲈 and rc independently represent a substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (c6_c3〇) aryl], substituted or unsubstituted (C6-C30) aryl ( C卜C3〇 Alkyl, RdY-[wherein Y represents S or 0, and Rd represents substituted or unsubstituted (C-C30) alkyl or substituted or unsubstituted (C6_C3〇) aryl], substituted Or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted CC2-C30) alkynyl, R23

R22 ^ ^21R22 ^ ^21

，但排除R4及 R5同時為氫或氣的情形； W，X ’ Y 及 Z 獨立表示-(CR31R32)n-、-(R31)C=(XR32)_、 一N(R33)-、-S- ' -0-、-Si(R34)(R35)-、-P(R36)_、 94916 6 201109420 -P(=0)(R37)-、_C(=0)-或-B(R38)-; R21至R23及R31至R38係與Ri至R3相同，其中R31至R38 各可經由具有或不具有稠合環之（C3-C30)伸烷基或 (C3-C30)伸烯基連結至相鄰取代基以形成脂環或單環或多 環之芳香環； 該雜環烷基及雜芳基可含有選自B、N、0、S、P(=0)、, except that R4 and R5 are both hydrogen or gas; W, X ' Y and Z independently represent -(CR31R32)n-, -(R31)C=(XR32)_, one N(R33)-, -S - ' -0-, -Si(R34)(R35)-, -P(R36)_, 94916 6 201109420 -P(=0)(R37)-, _C(=0)- or -B(R38)- R21 to R23 and R31 to R38 are the same as Ri to R3, wherein each of R31 to R38 may be bonded to the phase via a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring. An ortho substituent to form an alicyclic or monocyclic or polycyclic aromatic ring; the heterocycloalkyl and heteroaryl may contain a group selected from B, N, 0, S, P (=0),

Si及P之一個或多個雜原子；以及 m表示0，1或2之整數。 【實施方式】 本發明中，”烷基π，π烷氧基π及含有π烷基π部份之其 他取代基係包含直鏈或分支鏈物種兩者。本發明中，"環烷 基”包含單環烴以及多環烴如金剛烷基或雙環烷基。 本發明中，”芳基”係指藉由移除一個氫原子而衍生自 芳香族烴之有機基，且可包含4-至7-員，特別是5-或6-員，之單環或稠合環，包含由單鍵所連結之複數個芳基。 具體實例包含笨基、萘基、聯苯、蒽基、茚基、»基、菲 基、聯伸三苯基、祐基、茈基、蒯基、稠四苯基 (naphthacehyl)、丙二稀合苐基（f luoranthenyl)等，但不 限於此。萘基包含1-萘基及2-萘基，蒽基包含1-蒽基、 2-蒽基及9-蒽基，第基包含1-苐基、2-»基、3-苐基、4-苐基及9-苐基。本發明中，π雜芳基'1係指含有選自B、N、 0、S、P(=0)、Si及Ρ之1至4個雜原子作為芳香環骨架 原子，其餘之芳香環骨架原子為碳之芳基。其可為5-或6-員單環雜芳基或為與苯環縮合所形成之多環雜芳基，且可[s] 7 94916 201109420 為部份飽和者H雜芳基包含由單鍵所連結之超過一 個的雜芳基。雜芳基包含其中環中的雜原子可被氧化或四 級化以形成，例如，N-氧化物或四級鹽之二價芳基。具體 實例包含單環雜芳基如呋喃基、噻吩、吡咯基、咪唑某、_ 吡唑基、噻唑基、噻二唑基、異噻唑基、異卩琴唑基、^唑 基、唁一唾基、三哄基、四哄基、三唾基、四唾基、α夫咕 基、吡啶基、吡[[井基、嘧啶基、嗒哄基等，多環雜芳基如 本并α夫喃基、苯并嗟吩基、異苯并咬喃基、苯并_唾基、 笨并嗟唾基、苯并異噻唑基、苯并異卩琴唑基、笨并卩萼唑基、 異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹琳基、異 喹啉基、噌啉基、喹唑啉基、喹噚啉基、咔唑基、啡啶基、 苯并二噚苊基（benzodioxolyl)等，其Ν-氧化物（例如，吡 咬基N-氧化物’喹啉基N-氧化物）’其四級鹽等，但不限 於此。 本發明中’（C1-C30)烷基、三（C1-C30)烷基矽烷基、 二（a-C30)烷基（C6-C30)芳基矽烷基、（C6-C30)芳基 (C1-C30)烷基、（n-C30)烷氧基、（C1-C30)烷基硫基等之 院基部份可具有1 20個碳原子，更明確地為1至1〇個碳 原子。（C6-C30)芳基、二（C1-C30)烷基（C6-C30)芳基矽烷 基、三（C6-C30)芳基矽烷基、（C6-C30)芳基（C1-C30)烷基、 (C6-C30)芳氧基、（C6-C30)芳基硫基等之芳基部分可具有 6至20個碳原子，更明確地為6至12個碳原子。"（C3-C30) 雜芳基"之雜芳基可具有4至20個碳原子，更明確地為4 至12個碳原子。"（C3-C30)環烷基"之環烷基可具有3至 8 94916 201109420 20個碳原子，更明確地為3至7個碳原子。”（C2_C3〇)烯 基或快基之婦基或块基可具有2至20個碳原子，更明確 地為2至10個碳原子。 而且，本發明中’"經取代或未經取代"或者"具有或不 具有取代基"一詞係指Ri至R5及Ru至Ru的取代基可獨立 經選自氖、幽素、具有或不具有鹵素取代基之（c卜C3〇)烷 基、（C6_C30)芳基、具有或不具有（C6-C30)芳基取代基之 (C3-C30)雜芳基、5-至7-員雜環烷基、與一個或多個芳香 環稠合之5-至7-員雜環烷基、（C3-C30)環烷基、與一個或 多個芳香環稠合之（C6-C30)環烷基、三（C1-C30)烷基矽烷 基、二（(U-C30)烷基（C6-C30)芳基矽烷基、三（C6-C30)芳 基矽烷基、金剛烷基、（C7_C3〇)雙環烷基、（C2_C3〇)烯基、 (C2-C30)炔基、氰基、咔唑基、nr41R42、BR43R44、PR45R46、 P〇0)R4?R48[式中Ru至R48獨立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)芳基或者經 取代或未經取代之（C3-C30)雜芳基]、（C6-C30)芳基 (C1-C30)烷基、（C1-C30)烷基（C6-C30)芳基、（C1-C30)院 氧基' (C1-C30)烷基硫基、（C6-C30)芳氧基、（C6-C30)芳 基硫基、（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)芳 氧基戴氧基、緩基、硝基及經基所組成族群之一個或多個 取代基取代；或可連結至相鄰取代基以形成環。One or more heteroatoms of Si and P; and m represents an integer of 0, 1 or 2. [Embodiment] In the present invention, "alkyl π, π alkoxy π and other substituents containing a π alkyl π moiety include both linear or branched chain species. In the present invention, " cycloalkyl "contains monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or bicycloalkyl. In the present invention, "aryl" means an organic group derived from an aromatic hydrocarbon by removing one hydrogen atom, and may include a 4- to 7-member, especially a 5- or 6-member, a monocyclic ring or A fused ring comprising a plurality of aryl groups linked by a single bond. Specific examples include stupid, naphthyl, biphenyl, anthryl, fluorenyl, benzyl, phenanthryl, tert-triphenyl, ketone, fluorenyl, fluorenyl, naphthacehyl, propylene Base (f luoranthenyl), etc., but is not limited thereto. The naphthyl group includes 1-naphthyl group and 2-naphthyl group, and the fluorenyl group includes 1-fluorenyl group, 2-fluorenyl group and 9-fluorenyl group, and the first group includes 1-fluorenyl group, 2-» group, 3-mercapto group, and 4 - sulfhydryl and 9-mercapto. In the present invention, πheteroaryl '1 means one or four hetero atoms selected from the group consisting of B, N, 0, S, P (=0), Si and fluorene as an aromatic ring skeleton atom, and the remaining aromatic ring skeleton The atom is an aryl group of carbon. It 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 [s] 7 94916 201109420 is a partially saturated H heteroaryl group consisting of a single bond More than one heteroaryl group attached. The heteroaryl group includes a divalent aryl group in which a hetero atom in the ring can be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include monocyclic heteroaryl groups such as furyl, thiophene, pyrrolyl, imidazolyl, _pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoindazolyl, oxazolyl, oxime Base, triterpene, tetradecyl, trisal, tetras-s, alpha-frylidene, pyridyl, pyridyl [[well, pyrimidinyl, fluorenyl, etc., polycyclic heteroaryls such as Benzyl, benzoxenyl, isobenzotrienyl, benzo-saltyl, stupidinyl, benzisothiazolyl, benzisoxazozolyl, stupid carbazolyl, iso Indenyl, fluorenyl, carbazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, porphyrinyl, quinazolinyl, quinoxalinyl, oxazolyl, phenanthryl, Benzodioxolyl or the like, a quinone-oxide (for example, a pyridyl N-oxide 'quinolinyl N-oxide)' quaternary salt or the like, but is not limited thereto. In the present invention, '(C1-C30)alkyl, tri(C1-C30)alkyldecane, bis(a-C30)alkyl(C6-C30)aryldecyl, (C6-C30)aryl (C1) The -C30) an alkyl group, an (n-C30) alkoxy group, a (C1-C30)alkylthio group or the like may have 1 20 carbon atoms, more specifically 1 to 1 carbon atom. (C6-C30) aryl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl,(C6-C30)aryl(C1-C30)alkane The aryl moiety of the (C6-C30) aryloxy group, (C6-C30) arylthio group or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The "(C3-C30)heteroaryl" heteroaryl group can have from 4 to 20 carbon atoms, more specifically from 4 to 12 carbon atoms. The "(C3-C30)cycloalkyl" cycloalkyl group may have 3 to 8 94916 201109420 20 carbon atoms, more specifically 3 to 7 carbon atoms. The (C2_C3〇)alkenyl or fast-radical group or block group may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms. Moreover, in the present invention, '" substituted or unsubstituted "Or " with or without a substituent" means that the substituents of Ri to R5 and Ru to Ru are independently selected from the group consisting of ruthenium, ruthenium, with or without a halogen substituent (c An alkyl group, a (C6_C30) aryl group, a (C3-C30) heteroaryl group having or not having a (C6-C30) aryl substituent, a 5- to 7-membered heterocycloalkyl group, and one or more aromatic groups Ring-fused 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, (C6-C30)cycloalkyl, tri(C1-C30) alkane fused to one or more aromatic rings Base alkyl, bis((U-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl,adamantyl,(C7_C3〇)bicycloalkyl, (C2_C3〇) Alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, nr41R42, BR43R44, PR45R46, P〇0)R4?R48 [wherein Ru to R48 independently represent substituted or unsubstituted (C1-C30) An alkyl group, a substituted or unsubstituted (C6-C30) aryl group or substituted Unsubstituted (C3-C30)heteroaryl], (C6-C30)aryl (C1-C30)alkyl, (C1-C30)alkyl (C6-C30) aryl, (C1-C30) Oxy '(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) aryl A carbonyloxy group, a (C6-C30) aryloxymethoxy group, a buffer group, a nitro group, and one or more substituents of a group consisting of a group; or may be bonded to an adjacent substituent to form a ring.

Ri至R3可獨立表示氫、氘、鹵素、經取代或未經取代【 9 94916 201109420 之（C1-C30)烷基、經取代或未經取代之（C6_c3〇)芳其、疏 取代或未經取代之（C3-C30)雜芳基、經取代或未經二: (C3-C3G)觀基、魄钱未餘代之金㈣基、服+ [式中心及R1Z獨立表示經取代或未經取代之加）烷 基' 經取代或未經取代之（C6—C3〇)芳基、或者經取代或°未 經取代之（C3-C30 )雜芳基]或RVRcsi _ [式中Ra、Rb及rc獨 立表示經取代或未經取代之（C1 一⑽烧基或者經取代或未 經取代之（C6-C30)芳基];且匕及R5可獨立表示經取代或 未經取代之（C1-C30)烷基、經取代或未經取代之（C6_C3〇) 芳基、與一個或多個經取代或未經取代之（C3_C3〇)環烷基 稠合之經取代或未經取代之（C6_C3〇)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_員雜 環烷基、與一個或多個經取代或未經取代之芳香環稍合之 5至7員雜環烧基、經取代或未經取代之（c3_c3〇)環炫 基、或者與一個或多個經取代或未經取代之芳香環稠合之 CC3-C30)環烷基。Ri to R3 may independently represent hydrogen, deuterium, halogen, substituted or unsubstituted [(C1-C30)alkyl group of 9 94916 201109420, substituted or unsubstituted (C6_c3〇) aryl, sparsely substituted or unsubstituted Substituted (C3-C30)heteroaryl, substituted or unsubstituted: (C3-C3G) base, gold (4) base, service + [Formula and R1Z independently represent substituted or not Substituted) alkyl 'substituted or unsubstituted (C6-C3〇) aryl, or substituted or unsubstituted (C3-C30)heteroaryl] or RVRcsi _ [in the formula, Ra, Rb And rc independently represent substituted or unsubstituted (C1-(10) alkyl or substituted or unsubstituted (C6-C30) aryl]; and hydrazine and R5 independently represent substituted or unsubstituted (C1 -C30)alkyl, substituted or unsubstituted (C6_C3〇) aryl, substituted or unsubstituted with one or more substituted or unsubstituted (C3_C3〇)cycloalkyl ( C6_C3〇) aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted 5-7 to 7-membered heterocycloalkyl, with one or more substituted or unsubstituted Substitute Fang a 5- to 7-membered heterocycloalkyl, a substituted or unsubstituted (c3_c3〇)cyclodeptyl group, or a CC3-C30 fused to one or more substituted or unsubstituted aromatic rings) Cycloalkyl.

Ri至R3可獨立選自氫、氘、鹵素、炫基（如甲基、乙 基、丙基、丁基、戊基、己基、乙基己基、庚基、辛基等）、 芳基（如笨基、萘基、第基、聯苯基、聯三笨基、芘基、茈 基、螺雙f (spirobifluorenyl)基、丙二烯合苐基、蒯基、 聯伸二苯基等）、雜芳基（如二苯并噻吩基、二苯并呋喃基、 咔唑基、吡啶基、呋喃基、噻吩基、喹淋基、三哄基、嘧 啶基、嗒卩井基、喹噚啉基、啡啉基等）、環烷基（如環丙基、 % 丁基、環戊基、環己基等）、金剛烷基、胺基（如單-或二 94916 10 201109420 -苯絲基胺基、單—或二— •三綠喊基（如三甲基料基、三乙基傾基、二甲Γ乙 燒基等)、二烧基芳基_如二甲 等)、或三芳基傾基(如三苯基残基、三 般經取代或未經取代此。它們可如化學式⑴所定義 ML可獨立選自燒基如甲基、乙 戊基、己基、乙基己基、庚基、辛美耸.#甘土 丁基 基、第基、聯笨基、菲基、聯：笨絲苯基、萘 第基、丙二坤合第基、劍基、聯伸三苯基等；與一個或多 基稠合之芳基如u-二氫危基等，·雜芳基如二苯并 苯并咬喃基、十坐基L夫喃基、嘆吩 二1基、二哄基、•定基、塔啡基、轉琳基、啡啉 基荨，雜環烷基如嗎啉基、硫代嗎琳 Ν-嗎啉基、哌啶A、w⑽a盆哲^ 馬琳基、硫代 土辰^基、^辰咬基等；與-個或多個芳香環稠 ° a至7-貝雜環烧基如N_苯并娘咬基、n_苯并鱗 基等^環院基如環丙基、環丁基、環戊基、環己基、環庚 ，、環辛基等；與-個或多個芳香環稠合之環絲如苯并 裱己基等’·金剛垸基或雙環烧基如雙環[2‘ 2. 1]庚基等，但 不限於此。它們可如化學式⑴所定義般經取代或未― 代。 依據本發明之有機電場發光化合物可藉由下述化合物 予以示例，但不限於此。 。物 94916 11 201109420Ri to R3 may be independently selected from the group consisting of hydrogen, deuterium, halogen, thio (such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc.), aryl (such as Stupid, naphthyl, yl, biphenyl, triphenyl, fluorenyl, fluorenyl, spirobifluorenyl, propadienyl, fluorenyl, extended diphenyl, etc. Aryl (such as dibenzothiophenyl, dibenzofuranyl, oxazolyl, pyridyl, furyl, thienyl, quinolyl, tridecyl, pyrimidinyl, fluorenyl, quinoxalinyl, Phenanyl, etc.), cycloalkyl (such as cyclopropyl, % butyl, cyclopentyl, cyclohexyl, etc.), adamantyl, amine (eg, mono- or di-94916 10 201109420 - phenyl-based amine, Single- or two--three green bases (such as trimethyl base, triethyldecyl, dimethylhydrazine, etc.), dialkyl aryl (such as dimethyl), or triaryl (such as triphenyl residues, triple substituted or unsubstituted. They may be independently selected from the group consisting of alkyl, ethyl pentyl, hexyl, ethylhexyl, heptyl, octyl as defined in formula (1). Beautiful shrub. #甘土a base group, a base group, a phenyl group, a phenanthryl group, a phenyl group, a naphthyl group, a propylene group, a sword group, a triphenyl group, etc.; an aryl group fused to one or more groups Such as u-dihydrogen group, etc., heteroaryl such as dibenzobenzopyrene, decyl L-fyl, succinyl diphenyl, dimercapto, de-based, taphthyl, trans-lin , morpholinyl hydrazine, heterocycloalkyl group such as morpholinyl, thiomorphine Ν-morpholinyl, piperidine A, w (10) a pot philanthropy ^ Ma Linji, thio-terenyl group, ^ Chen bite base, etc.; Condensed with one or more aromatic rings, a to 7-beta heterocycloalkyl, such as N-benzoin, n-benzo fluorenyl, etc., such as cyclopropyl, cyclobutyl, cyclopentyl a ring, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.; a ring filament fused to one or more aromatic rings, such as a benzoxanyl group, etc., or a bicyclic alkyl group such as a bicyclo[2' 2. 1 Heptyl and the like, but are not limited thereto. They may be substituted or not as defined by the chemical formula (1). The organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but is not limited thereto. 11 201109420

12 94916 20110942012 94916 201109420

依據本發明之有機電場發光化合物可藉由方案 之，不限於此： 衣 [方案1]The organic electroluminescent compound according to the present invention can be used by a solution, and is not limited thereto: [Scheme 1]

置，本發明係提供一種有機電場發光裝 多種化學式Π)所+ > 、丁另例：曰匕3種或 -心Γ 有機電場發光化合物。有機層可包八 一種或多種化學式⑴所示之有機電場發光化合物作為電3 94916 13 201109420 場發光主體且可包含一種或多種摻雜劑 機電場發光裝置之摻雜劑並無特別限制 (2)或化學式（3)所示之化合物： 。使用於本發明有 ，但可選自化學式The present invention provides an organic electric field luminescent device, a plurality of chemical formulas, >, and another example: 曰匕3 species or - Γ Γ organic electroluminescent compounds. The organic layer may comprise eight or more organic electroluminescent compounds of the formula (1) as a dopant for the field emission device and may include one or more dopants. The dopant of the electric field illuminating device is not particularly limited (2) Or a compound represented by the chemical formula (3): . Used in the present invention, but may be selected from the chemical formula

Ar. 13* -N. (2) M2 式中 Arn及Am獨立表示經取代或未經取代t(a_c3〇)烷 基、經取代或未經取代2(C6_C3〇)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)烧基胺基' 經取代或未經取代之5_至 員雜環烷基、與一個或多個經取代或未經取代之芳香環稠 5之5-至7-員雜環烧基、經取代或未經取代之 環院基、或與一個或多個經取代或未經取代之芳 (C3-C30)環院基，或Am與Ari2經由具有或不具有祠入 環之（C3-C30)伸烷基或（C3-C30)伸烯基連結以形成腊學二 單環或多環之芳香環； <Ar. 13* -N. (2) M2 where Arn and Am independently represent substituted or unsubstituted t(a_c3〇)alkyl, substituted or unsubstituted 2(C6_C3〇)aryl, substituted or not Substituted (C4-C30)heteroaryl, substituted or unsubstituted (C6_c3〇)arylamino, (C1-C30)alkylamino' substituted or unsubstituted 5_ to hetero a cycloalkyl group, a 5- to 7-membered heterocycloalkyl group bonded to one or more substituted or unsubstituted aromatic rings, a substituted or unsubstituted ring-based group, or with one or more Substituted or unsubstituted aryl (C3-C30) ring, or Am and Ari2 linked via a (C3-C30) alkyl or (C3-C30) alkyl group with or without an indole ring to form a wax Learn two monocyclic or polycyclic aromatic rings; <

Ans表示經取代或未經取代之（C6-C30)芳基、羥取代 或未經取代之（C4-C30)雜芳基或選自下述結構之取代及 (當c為1時）： 土 201109420Ans represents a substituted or unsubstituted (C6-C30) aryl, hydroxy-substituted or unsubstituted (C4-C30)heteroaryl group or a substituent selected from the following structures and (when c is 1): 201109420

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)伸雜芳基或選自下述結構之取代 基（當c為2時）： R 1Π2 R t〇3An3 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 structure (when c is 2) : R 1Π2 R t〇3

Ar14及Ar15獨立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；Ar14 and Ar15 independently represent a substituted or unsubstituted (C6-C30) extended aryl, substituted or unsubstituted (C4-C30) heteroaryl group;

Run至Ri〇3獨立表示氫、氘、經取代或未經取代之 (a-C30)烷基或者經取代或未經取代之（C6-C30)芳基； d表示1至4之整數；以及 e表示0或1之整數。Run to Ri〇3 independently represents hydrogen, deuterium, substituted or unsubstituted (a-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.

I 化學式（2)或（3)所示之摻雜劑化合物可藉由下述化合 物予以示例，但不限於此： 15 94916 201109420The dopant compound represented by the formula (2) or (3) can be exemplified by the following compounds, but is not limited thereto: 15 94916 201109420

16 94916 20110942016 94916 201109420

本發明之有機電子裝置中，除了化學式⑴所示之有機 電場發光化合物外，有機層可同時進一步包含選自芳基胺 化合物及苯乙烯基芳基胺化合物所紐成群族之一種或^種 化合物。芳基胺化合物或苯乙烯基芳基胺化合物示例於韓 國專利申請案第 10-2008-0123276，10-2008-0107606 或 10-2008-0118428號，但不限於此。 再者，本發明之有機電場發光裝置中，除了化學式G) 所示之有機電場發光化合物外，有機層可進一步包含選自 第1族之有機金屬’第2族，第4周期和第5周期過渡金 屬，鑭系金屬及d-過渡元素所組成群族之一種或多種 屬。有機層可包含電場發光層及電荷產生層。 “ 再者’除了有機電場發光化合物外，有機層可 -步包含發出k光’綠光或紅光之—層或多層有機電場= 17 94916 201109420 光層，以體現發白光之有機電場發光裝置。發出藍光，& 光或紅光之化合物可以見述於韓國專利申請案第 10-2008-0123276 ’ 10-2008-0107606 或 10—2008-0118428 號之化合物示例之，但不限於此。 個 本發明之有機電場發光裝置中，可在電極對中之 或兩個電極的内表面上設置選自硫屬元素化物 (chalcogenide)層’金屬鹵化物層及金屬氧化物層之；（支 文稱為"表面層"）。更明確地說，矽或鋁之硫屬元素化物（勹 含氧化物）層可設置在電場發光介質層的陽極表面上，而^ 屬鹵化物層或金屬氧化物層可設置在電場發光介質層的降 極表面上。可由此獲致工作安定性。硫屬元素化物可為 例如，Si0x(l$x$2) ’ A10x(lsxs 1. 5)，Si〇N，SiAi_ 等。金屬鹵化物可為，例如’ LiF，MgF2，CaFz，稀土金 氟化物等。金屬氧化物可為，例如，CszO，LhO，Mg〇，§!>〇 BaO ， CaO 等。 依據本發明之有機電場發光裝置中，較佳係亦在由 所製造之電極對之至少一表面上配置電子傳送化合物與還 原性摻雜劑的混合區域，或電洞傳送化合物與氧化性捧雜 劑的混合區域。在此種情形下，由於電子傳送化合物被還 原成陰離子，促進電子自混合區域注入且傳送至電場發光 介質。此外，由於電洞傳送化合物被氧化成陽離子，促進 電洞自混合區域注入且傳送至電場發光介質。較佳之氧化 性摻雜劑包含各種路易士酸及接受體化合物。較佳之還原 性摻雜劑包含驗金屬，鹼金屬化合物，驗土金屬，稀土金 94916 18 201109420 屬’及其混合物。再者，可藉由使用還原性摻雜劑層作為 電荷產生層而製造具有兩層或更多層電場發光層之發白 電場發光裝置。 優越功效 由於依據本發明之有機電場發光化合物具有良好的發 光效率及優異的壽命性質，故其可使用於製造具有非常^ 越工作壽命的0LED裝置。 發明模式 參知、依據本發明之有機電場發光化合物，其製備方 法，及使用該化合物之裝置的發光性質進一步說明本發 明。然而，下述實施例係僅供說明之目的而其非用於限制 本發明的範圍。 [製備例1]化合物3之製備In the organic electronic device of the present invention, in addition to the organic electroluminescent compound represented by the chemical formula (1), the organic layer may further contain one or a group selected from the group consisting of an arylamine compound and a styrylarylamine compound. Compound. The arylamine compound or the styrylarylamine compound is exemplified in 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 represented by the chemical formula G), the organic layer may further comprise an organometallic selected from the group 1 'Group 2, the 4th cycle and the 5th cycle. One or more genera of a group of transition metals, lanthanide metals, and d-transition elements. The organic layer may include an electric field luminescent layer and a charge generating layer. In addition to the organic electric field luminescent compound, the organic layer may comprise a layer of light or green light or a layer of organic light = 17 94916 201109420 to reflect the organic light-emitting device that emits white light. The compound which emits blue light, & light or red light can be exemplified by the compound example of Korean Patent Application No. 10-2008-0123276 ' 10-2008-0107606 or 10-2008-0118428, but is not limited thereto. In the organic electric field light-emitting device of the invention, a metal halide layer and a metal oxide layer selected from a chalcogenide layer may be disposed on the inner surface of the electrode pair or the two electrodes; "Surface layer"). More specifically, the chalcogenide or tantalum chalcogenide (勹-oxide) layer may be disposed on the anode surface of the electric field luminescent medium layer, and the halide layer or metal oxide The layer may be disposed on the lowering surface of the electroluminescent luminescent medium layer, thereby achieving operational stability. The chalcogenide may be, for example, Si0x(l$x$2) ' A10x(lsxs 1. 5), Si〇N, SiAi_ Etc. Metal halides can For example, 'LiF, MgF2, CaFz, rare earth gold fluoride, etc. The metal oxide may be, for example, CszO, LhO, Mg〇, §!> 〇BaO, CaO, etc. In the organic electric field light-emitting device according to the present invention Preferably, a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant is disposed on at least one surface of the electrode pair to be fabricated. Next, since the electron transporting compound is reduced to an anion, electrons are injected from the mixing region and transported to the electric field illuminating medium. Further, since the hole transporting compound is oxidized to a cation, the hole is facilitated from the mixed region and transported to the electric field illuminating medium. Preferably, the oxidizing dopant comprises various Lewis acids and acceptor compounds. Preferably, the reducing dopant comprises a metal, an alkali metal compound, a soil metal, a rare earth gold 94916 18 201109420 genus and mixtures thereof. A white-like electric field luminescence having two or more layers of an electroluminescent layer can be produced by using a reducing dopant layer as a charge generating layer Device. Advantageous Efficacy Since the organic electroluminescent compound according to the present invention has good luminous efficiency and excellent lifetime properties, it can be used for manufacturing an OLED device having a very long working life. The invention is further illustrated by the electroluminescent compound, the process for its preparation, and the luminescent properties of the device using the compound. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the invention. [Preparation Example 1] Preparation of compound 3

化合物1-1的製備 將2-(曱氧基羰基）苯基硼酸（10公克（g)，55. 55毫莫 耳（mmol))，1，3, 5-三漠笨（19. 2g，61. 12 mmol) ’ Pd(PPh3)4 19 94916 201109420 (1. 9g，0. 03mmol) ’ 2M K2C〇3水溶液（80 毫升（mL))，曱笨 (200mL)及乙醇（50mL)混合，再於迴流下攪拌之。5小時之 後，冷卻至室溫後，添加蒸餾水。以EA萃取且以無水MgS〇4 乾燥後’在減壓下蒸餾，接著管柱分離，產出化合物1-1 (13. 5g，36. 38mmol，65. 73%)。 化合物1-2的製備 將化合物卜 1(13. 5g ’ 36. 38mmol)溶解在 THF(300mL) 中。緩慢地添加溴化曱基鎂（36.48mL，l〇9.44mmol，3. OM， 在二乙醚中）後，於60°C攪拌此混合物。ι〇小時之後，冷 卻至室溫後’缓慢地添加蒸館水。以EA萃取且以無水MgS〇4 乾燥後’在減壓下蒸德，接著管柱分離，產出化合物1一2 (12g，32. 42mmol，90. 07%)。 化合物1-3的製備 將化合物 l-2(12g ’ 32.42mmol)與错酸（2〇〇mL)及 H3P〇4(300mL)混合，然後於12(TC攪拌之。12小時之後， 冷卻至室溫後’添加蒸餾水。以EA萃取且以無水MgS〇4乾 燥後，在減壓下蒸餾，接著管柱分離，產出化合物卜吖％， 25.56mmol ’ 78.85%)。 化合物1-4的製備 將化合物1-3溶解在MC(lOOmL)中。添加a1C13 (5. !lg， 38· 34mm〇l)及酞酸酐（3. 7g，25. 56咖〇1)後，使混合物於4〇t： 擾拌12小時。冷卻至室溫後’添加蒸館水。以mc萃取，以 HC1水溶液沖洗且以無水MgS〇4乾燥後，在減壓下蒸餾，接 著管柱分離’產出化合物’ 23. 99_，93,_)。 94916 20 201109420 化合物1~5的製備 將化合物1·_4 (12g，23. 99mm〇1)與醋酸（5〇mL)及硫酸 (50mL)混合，然後於1〇(rc攪拌之。5小時之後，冷卻至^ ’皿後添加条餾水。以NaOH水溶液中和，以MC萃取且以 無水MgSCU乾燥後，在減壓下蒸餾，接著管柱分離，產出 化合物 1-5 (3. 6g，7. 46mmol，31. 12%)。 化合物1—6的製備 將2 (甲氡基羰基）苯基硼酸（3. 35g，18. 66mmol),化 合物卜5(3· 6g，7. 46mmol)，Pd(PPh3)4(0. 43g，0· 37mm〇i)， 2M K2C〇3水溶液（UmL)，甲苯（50mL)及乙醇（25mL)混合再 在迴流下_之。1M、時之後，冷卻至室溫後，添加蒸儉 水以EA萃取且以無水MgS〇4乾燥後，在減壓下蒸餾，接 者笞柱刀離，產出化合物1 一6(知，& 74mm〇i，9〇. 47%)。 化合物1-7的製備 將化合物 l-6(4g ’ 6· 74 romol)溶解在 THF(lOOmL)中。 缓慢地添加溴化甲基鎂（13 49乩，4〇 49mm〇1，3 〇M，在二 乙醚中）後，於6(TC攪拌此混合物。10小時之後，冷卻至 至溫後，緩慢地添加蒸餾水。以EA萃取且以無水MgS〇4乾 燥後，在減壓下蒸餾，接著管柱分離，產出化合物卜7 (3. 2g，5. 39mmol，80. 11%)。 化合物1-8的製備 將化合物 1-7(3. 2g ’ 5. 39mmol)與醋酸（50inL)& H3P〇4 (50mL)混合，然後於120^攪拌之。12小時之後，冷卻至 室溫後，添加蒸餾水。以EA萃取且以無水MgS〇4乾燥後，[ 21 94916 201109420 產出化合物1—8(2. 3g，4 在減壓下蒸餾’接著營柱分離， mmol ， 76.65%)。 化合物1 - 9的製備 將溴笨（1. 75g，π. i5mm〇i)添加至 THF(4〇mL)，然後 於-78°C 緩慢地添加 n_BuLi(4· 6ml，u. 56醜〇1，2 5M，在 己院中）。H、時後，加入化合物卜8(2 3g，413随〇1)。 緩慢地加熱至室溫後，；l〇小時之後，添加蒸餾水。以Ea 萃取且以無水MgS〇4乾燥後，在減壓下進行蒸餾。所得之 產物在沒有進一步純化下使用於下一步驟。 化合物3的製備 將粗製化合物 l-9(3.2g)與 KI(2.45g’ 14. 81mmol)， NaH2P〇2H2〇(3. 13g，29. 62mmol)及醋酸（50mL)混合，然後加 熱至12 0 C。14小時之後，冷卻至室溫後，添加蒸館水。 在減壓下過濾由此所製得之固體再以NaOH水溶液沖洗 之。管柱分離，產出化合物3 (1. 6g ’ 2. 35mmol，63. 52%)。 [製備例2]化合物24的製備Preparation of Compound 1-1 2-(decyloxycarbonyl)phenylboronic acid (10 g (g), 55.55 mmol (mmol)), 1,3, 5-trim (19. 2 g, 61. 12 mmol) ' Pd(PPh3)4 19 94916 201109420 (1. 9g, 0. 03mmol) ' 2M K2C〇3 aqueous solution (80 ml (mL)), mixed with stupid (200mL) and ethanol (50mL), then Stir under reflux. After 5 hours, after cooling to room temperature, distilled water was added. After extraction with EA and dried over anhydrous MgSO4, <RTI ID=0.0>>> Preparation of Compound 1-2 Compound 1 (13.5 g "36.38 mmol) was dissolved in THF (300 mL). After the addition of bismuth bromide magnesium (36.48 mL, 1.94 mmol, 3.OM in diethyl ether), the mixture was stirred at 60 °C. After 〇 〇 hours, cool to room temperature and then slowly add steamed water. After extraction with EA and dried over anhydrous MgSO.sub.4, evaporated under reduced pressure, and then the column was separated to yield compound 1-2 (12 g, 32.42 mmol, 90.07%). Preparation of Compound 1-3 Compound l-2 (12 g '32.42 mmol) was mixed with the wrong acid (2 mL) and H3P〇4 (300 mL), then stirred at 12 (TC). After 12 hours, cooled to room After heating, distilled water was added. After extraction with EA and drying with anhydrous MgS 4 , the mixture was distilled under reduced pressure, and then separated by a column to yield compound bromide, 25.56 mmol ' 78.85%. Preparation of Compound 1-4 Compound 1-3 was dissolved in MC (100 mL). After adding a1C13 (5. !lg, 38·34 mm〇l) and phthalic anhydride (3.7 g, 25.56 curry 1), the mixture was stirred at 4 Torr for 12 hours. After cooling to room temperature, add steamed water. It was extracted with mc, washed with an aqueous solution of HC1 and dried over anhydrous MgS?, and then distilled under reduced pressure to separate the 'produced compound' 23.99_, 93, _). 94916 20 201109420 Preparation of Compounds 1 to 5 Compound 1·_4 (12 g, 23.99 mm 〇1) was mixed with acetic acid (5 〇mL) and sulfuric acid (50 mL), and then stirred at 1 Torr (5 hours later, After cooling to a dish, the mixture was added to a solution of 1-5 (3.6 g, 7). 46 mmol, 31. 12%) Preparation of Compound 1-6 2 (Methylcarbonylcarbonyl)phenylboronic acid (3.35 g, 18.66 mmol), Compound 5 (3·6 g, 7.46 mmol), Pd (PPh3) 4 (0. 43g, 0·37mm〇i), 2M K2C〇3 aqueous solution (UmL), toluene (50mL) and ethanol (25mL) were mixed and refluxed. 1M, then cooled to room After the temperature, the distilled water was added and extracted with EA and dried with anhydrous MgS〇4, and then distilled under reduced pressure, and then the column was separated, and the compound 1-6 was obtained (know, & 74 mm〇i, 9〇. 47%) Preparation of Compound 1-7 Compound l-6 (4 g '6·74 romol) was dissolved in THF (100 mL). Methylmagnesium bromide (13 49 乩, 4 〇 49 mm 〇1) was slowly added. 3 〇M, in diethyl ether), at 6 (TC The mixture was mixed. After 10 hours, after cooling to the temperature, distilled water was slowly added, extracted with EA and dried over anhydrous MgS 4 , then distilled under reduced pressure, and then separated by column to yield compound b. 2g, 5. 39mmol, 80. 11%) Preparation of compound 1-8 Compound 1-7 (3.2 g '5.39 mmol) was mixed with acetic acid (50 inL) & H3P〇4 (50 mL), then at 120 After stirring for 12 hours, after cooling to room temperature, distilled water was added. After extraction with EA and drying with anhydrous MgS 4 , [ 21 94916 201109420 yielded compound 1-8 (2.3 g, 4 distillation under reduced pressure) 'Next camp separation, mmol, 76.65%.) Preparation of compound 1 - 9 Bromo bromide ( 1. 75 g, π. i5 mm〇i) was added to THF (4 〇 mL) and then slowly added at -78 ° C n_BuLi (4·6ml, u. 56 ugly 1, 2 5M, in the hospital). H, after the time, add compound b 8 (2 3g, 413 followed by 1). Slowly heated to room temperature; After 1 hour, distilled water was added, extracted with Ea and dried over anhydrous MgS 4 and then distilled under reduced pressure. The obtained product was used in the next step without further purification. . Preparation of compound 3 Crude compound l-9 (3.2 g) was mixed with KI (2.45 g ' 14.81 mmol), NaH2P〇2H2 oxime (3.13 g, 29.62 mmol) and acetic acid (50 mL), then heated to 12 0 C. After 14 hours, after cooling to room temperature, steamed water was added. The solid thus obtained was filtered under reduced pressure and washed with an aqueous NaOH solution. The column was separated and the compound 3 was obtained (1. 6 g ' 2. 35 mmol, 63. 52%). [Preparation Example 2] Preparation of Compound 24

化合物2-1的製備 以與製備例1之化合物1-6相同之製備方式’但使用 94916 22 201109420 化合物 l-5(5g ’ 10.37mmol)及 2、、， 25· 92mmol)，製備了化合物2~1(4肖基苯基爾（4. %， 化合物 2-2 的製備 ’ 7g’ δ. 29賴01，79. 96%)。 曰將化合物2-K4.7g，8為㈣與亞碟酸 混合’然後在迴流下攪拌之。乙‘（5〇mL、 小時之德，；么 > 在減壓下蒸鶴後，管柱分離，產 v卩至室溫且 mmol > 60. 〇〇%) 〇 化口物 2 2(2. 5g ’（ 97 化合物2-3的製備 將化合物 2-2(2.5g，4.97mmnl、 1101)，碘苯（2 21 咖〇1)，Cul(1.89g，9.94mmol)，'、 mi，19. 89 K2C〇3(2. 75g，iq δη 及 1，2-二氯苯（50mL)混合，然德 ^ iy-«9niin〇i) ^ κ 後知熱至190°C。24 t + 後，冷卻至室溫後，在減壓下蒸 小時之 且以EA萃取後，在減壓下蒸餾，雉著其柱八 > 加瘵餾水 物 2-3(2. 7g，4. 12mmol，82, 97%) 產出化合 化合物2-4的製備 以與製備例1之化合物1〜9知鬥 相同之製備方式， 化合物2-3 (2. 7g，4. 13mmol)，制 但使用 + 製備化合物2〜4。邮1 產物在沒有進一步純化下使用於下一步驟。 所件之 化合物24的製備 以與製備例1之化合物.3相同之製備方式，但 製化合物2-4(3. 2g)，製備化合物24(1. 6g，2 〇5mm用杈 49. 98%)。 咖〇卜 依據製備例1至4之程序製備化合物1至31。士 l 由此所f 攝之有機電場發光化合物的jNMR及MS/FAB數據示於f 、 9491(5 23 201109420 表1 化合物 ΧΗ NMR (CDC13, 200 MHz) MS/FAB 實測 計算 1 δ = 1.72 <12H, s) , 1.78 <6H, s) r 2.64(6Hr s> , 7.24-7.28(2H, m> , 7.35-7.38(3H, m> , 7.44(1H, m) , 7.55(1H, m) , 7.6K1H, m) , 7.76(1H, s) f 7·87(1Η,π〇 , 7.98<2H,m> , 8.07UH, s) , 8·09(1Η, m> 554.76 554.30 2 δ = 1.48(18H, s) f 1.72(12H, s) , 1.78(6H, s), 7.24-7.28(2H/ m) , 7.35-7.38(3H, m) , 7.44(1H, o〇 , 7·55(1Η, m> , 7 · 61 (1H, n〇 , 7 · 76 (1H, s> , 7.87 (lH,m) , 7.98 (2H,m) , Β·07(1Η, s) , B.09(1H, m) 638.92 638.39 3 δ = 1.72(12H, s) , 1.78(6Hf s) , 7.24-7.28(2H, m), 7.38-7.44(6H, m>, 7.51-7.S5(9H, m>, 7.61(lHf m>, 7.76(1Η, s) , 7·87-7.91(3H, m), 8.07(lHf s), 8.09(lHf m) 678.90 678.33 4 5 = 1.72(12H, s) , 1.78(6H, s> f 7.24-7.28(2H, m) , 7.38-7.44(4H, m) , 7.55 (5H, m) , 7.61(3日, n) , 7-76(lH, s> , 7.Θ7-7.9Κ3Η, m) , 8.04(2H, m) f 8.07(1H, s) r 8.08-8.09(3H, m> , 8.42 (2H, m) , 8.55(2H, m> 779.02 779.36 5 δ = 1.72<12H, s) , 1.78(6H, s> , 7.24-7.28(2H, m> , 7.38-7.44(4Hf m) , 7.55-7.61(8H, m), 7,73<2H, m)r 7.76(lHf s) r 7.87-7.92(5Hf m), 8(4H, m>, 8.07(1H, s), 8.09(1H, m) 779.02 779.36 6 δ = 1.72(12H, s) , 1.78(6H, s) , 2.34(6H, s), 7.24-7.44(14H, m> , 7.55(1H, m) , 7.61(1H, m), 7.76(1H, s) , 7.87-7.9K3H, m) , 8.07(1H, s), 8.09(1H, m) 706.95 706.36 7 δ = 1.72(12H, s) , 1.78(6H, s), 2.34(6H, s), 7.19-7.44(12H, m) , 7.55(1H, a) , 7.61(1H, m), 7.76(1H, s), 7.79(2H, m), 7.87-7.91(3H, m), B.07(1H, s), 8.09(1H, m) 706.95 706.36 8 5= 1.72<12H, s) , 1.78(6H, s), 2.32{6H, s), 7.24-7.44(12H, m) , 7.55(1H, m) , 7.61-7.67(3H, a), 7.76(1H, s), 7.87-7.91(3H, m), 8.07(1H, 706.95 706.36 24 94916 201109420 s>, 8·09(1Η, m) 9 5= 1.72(12H, s) , 1.78(6H, s) , 2.34(12H, s), 7.24-7.31(4H, m), 7.38-7.44(4H, m), 7.55-7.61(6H, m) , 7.76(1H, s) , 7.87-7.91(3H, m), 8.07(1H, s), 8.09(1H, m) 735.01 734.39 10 δ = 1.72(12H, s> , 1.78(6H, s> , 2.34(6H, s), 2.59(6H, s) , 7.1(2日，m) , 7.16(2H, m) f 7.24-7.28<2H, m) , 7.38-7.44(4H, m) , 7·55(3Η, m) , 7.61(1H, m) , 7.76(1H, s> , 7.87-7.91(3H, m), 8·07(1Η, s), 8.09<1H, m) 735.01 734.39 11 δ = 1·72(12Η, s) , 1.78 (6H, s) , 7·24-7·3(6Η, 7.38-7·44(8ΗΓ 7·55(1Η, m), 7·61(1Η, tn> , 7.76(1H, s) , 7.87-7.91 (3H, m> , 8.07(1H7 s), 8.09(1H, m) 714.88 714.31 12 δ == 1.72 (12H, s) , 1.78 (6H, s> , 7.24-7.28 (2H, 7.3S-7.44<4H, m), 7.55(1H, 7.61<1H, m> , 7.76(1H, s) , 7·82-7·91(11Η, m> , 8.07(1H, s>, 8.09<1H, m) 728.92 728.32 13 δ = 1.35(18H, s> , 1.72(12H, s) , 1·78(6Η, s), 7.24-7.28(2H,, 7.37-7.44(12H, m> , 7.55<1H, m) , 7.61(1H, m>, 7.76(1H, s> , 7.87_7.91 (3H, cn) , 8.07(1H, s) , 8.09(1H, m) 791.11 791.45 14 δ = 1·72(20Η, m) , 1.72 (OH, s> , 1.78 (6H, s), 2.74<8H,n〇 , 6.88(2H,m> , 6.98(2H,ta) f 7.15<2H, n>, 7.24-7.28(2H, m>, 7.38-7.44(4H, m) / 7.55(1H, m)f 7.61(lHf m)r 7.76(1H, s>, 7.87-7.91(3H, m)f 8.07(1H, s), 8.09(1H, m) 787.08 786.42 j 15 · • 5 = 1,72(12H, s)f 1,78(6H, s> , 7·1(2Η, n〇 , 7.24-7.28(2H, m}, 7.38-7.55(9Hf m), 7.61-7.63(3Hf m) , 7.76(1H, s) , 7.87-7.92(5Hf 780.99 780.35 25 94916 201109420 m) , 8.07(1H, s) , 8.09(1H, m) , 8.42(2H, m) 16 δ = 1·72(12Η, s) , 1.78(6H, s> , 3·83(6Η, s> , 7·05(4Η, m> , 7·24-7·28(2Η, , 7·3Β-7·44(4Η, Da), 7.55(lHf m) , 7.61(1H, m) f 7.68(4H, m), 7·76(1Η, s> , 7.87-7.91 (3H, m) , 8.07(1H, s> , 8.09(1H, m) 738.95 738.35 17 δ = 1.72(12H, s) , 1.78(6H, s) , 7.24-7.28 (2H , bl) , 7.38-7.44(8H/ m) , 7.55(1H, m>, 7.61<lH, 7·68(4Η, m), 7·76<1Η, s>, 7.87-7,91(3H, m) , 8.07(1R, s) , 8.09(1H, m) 814.90 814.30 18 5 = 0.25(18H, s> , 1.72(12H, s> , 1·78(6Η, s> , 7.24-7.28(2H, m) f 7,38-7.46(8H, m) , 7.55(1H, 7·61(1Η, 7·76(1Η, s>, 7·77(4Η, m>, 7.S7-7.91(3H, m) , 8.07(lHf s) , 8.09(lHf m) 823.26 822.41 19 δ = 1.72(12Hf s) f 1.78(6Hf s) f 7.24-7.28(2Hf m} , 7.37-7.55(39H, m> , 7.61<1H, m> , 7.76(1H, s) , 7.87-7.91(7H, m> , 8·07(1Η, s) , 8.09(1H, 1195.6 8 1194.50 20 δ = 1·72(12Η, s) , 1.78(6H, s) , 1 · 96 (4Hr m), 2.76(4H,m) f 3.06(4H,m) , 6.55 (2H,m) , 6,72(2H, m), 7·05-7·07(4Η, m>, 7.24-7.28(2H, m), 7.38-7.44(4H, m), 7.55(1H, 7.61(1H, m>, 7.69(1H, s), 7·87·7·91(3Η, m>, 8(1H, s>, 8.09(1Η, m) 789.06 788.41 21 δ = 1.71(12H, m) , 1.72(12H, s) , 1.78(6H, s), 2.01-2.02(18H, m), 7.24-7.28(2H, m), 7.35-7.38(3H, xn) , 7.44(1H, m) , 7.55(1H, m), 7.61(lH,m) , 7.76(1H, s) , 7.87(lH,m) , 7.98(2H, n) , 8.07(1H, s), 8.09(1H, m) 795.14 794.49 22 5 = 0.66(18H, s) , 7.33-7.4K6H, m), 727.12 726.26 26 94916 201109420 7·51-7.52(10H, m) Λ 7·SI(2H, m) , 7.89-7.91<4H, m>, 8-23(lH, s), 8,25(1H, s) 23 δ = 7·39-7.41(4Η, 7.5-7·52(12Η, m), 7·91(4Η, s> , 7·91(ΟΗ,π〇 , 7.98(2H,m) , 8·45(2Η, m> 648.86 648.10 24 δ = 7.25(2H, m) , 7.33-7.52(23H, m> , 7.58(6H, m) , 7.91(4H, s) r 7 · 91-7.94 (2H, m> , 8.55(2H/ tn) 825.99 825.31 25 δ = 1·72(12Η, s) , 1.78(6H, s> , 2·45(3Η, s), 7.24·7·28(3Η, m) , 7·38-7·44(4H, m), 7.51-7,55(9H, m} , 7,61(1H, m>, 7.7(1H, m>, 7.76(1H, s) , 7.85-7.87(2H, m) , 8*07(1H, s> , 8.09(1H, m) 692.93 692.34 26 δ = 1·72<12Η, s) , 1.78<6H, s> , 7·24-7.28(2ΗΓ , 7·38-7·44(3Η, m>, 7·51-7·61(13Η, m), 7·73(2Η, m), 7·76(1Η, s), 7·87_8(8Η, 8.07(1H, s), 8·09-8·13(2Η, m) 855.00 854.39 27 δ = 1.72 (12Hf s) , 1.78(6H, s> , 2.34(6H, s), 7.18(1H, m) , 7.24(1H, m) , 7.35-7.41 (6H, m), 7.51-7.52 (8H, m) f 7.75(lHf m) , 7.76(1H, s) r 7.91-7.97(3H, m> , 8.07(1H, s> 706.95 706.36 28 δ = 1.72(12H, s> , 1.78(6H, s) , 2.34(6Hr s> , 2.45(3H, s> , 7.18(1H, m) , 7.24-7.25 (2H, m), 7.35 (1H, m) , 7.41(3H, m>, 7.51-7.52 (8H, m), 7.7-7.75(2H, m) , 7.76(1H, s) , 7.85(1H, m), 7·97(1Η, m) Γ 8·07(1Η, s> 720.98 720.38 29 [ • 5 = 1.72 (12H, s) , 1.78 (6H, s) r 7.41 (5H, m), 7.51-7.52(20H, m> , 7.61-7.63(2H, m) , 7.69(1H, n) f 7.76(1H, s), 7.77(lHf m) f 7.83(lHf m), 7.93-7.97 (2H, m> , 8.07<1H, s) , 8·13·8.15(2H, 907.19 906.42 27 94916 201109420 m) 30 31 δ= S)/ l.VBtSH, — 7.2SUH, n〇 , 7.41(4H, tt> , 7.S1、7 S2(ieH 的， 7.63(1H, m), 7.69-7.7(2H, »), 7.76(1H/ s), 7.77UH,d83-7.S5<2H, m), 7 93(ih,( 8.07(1H, s), 8.15(1H, m) 5= 1.72(12H/ s), l.78(6Hf 6.81-6.83(3H, m,, 7.03(1H, m), 7.2.728(6h, a), 7.38-7.44(4H, m) , 7.51-7.55(9h 7.61(lH,m> , 7.75(lH,m> , 7·76<1Η, s) , 7 87(1H, m) , 8.07(1H, s), 8.09(1H, m) ' ' 845.12 846.11 844.41 845.30 [實施例1]使用依據本發明之有機電場發光化合物之〇咖 裝置的製造 使用依據本發明之有機電場發光化合物製造了 〇LED 裝置。 首先’使用二氯乙稀，丙乙醇及蒸德水對由〇咖 之玻璃（Samsung Corning出品）所獲得之透明電極IT〇薄 膜（15Ω/ϋ)施加超音波清洗’接著，在使用之前貯存在異 丙醇中。 然後，將ΙΤ0基板裝配在真空蒸氣沉積設備的基板夾 中，再將4,4’，4”-叁（Ν，Ν-(2-萘基）__苯基胺基）三笨基胺 (2-ΤΝΑΤΑ)放置在真空蒸氣沉積設備的單元（cell)中，然後 抽氣直至室中真空度為10 6托。然後對該單元施加電流以 使2-TNATA蒸發，由而在no基板上形成厚度為6〇nm之電 洞注入層。然後，將n，n’_雙（α_萘基）_N，N，_二苯基 -4,4 _二胺（NPB)放置在真空蒸氣沉積設備的另一單元中， 對該單元施加電流以使NPB蒸發，由而在電洞注入層上形 94916 28 201109420 成厚度為2〇nm之電洞傳 =電洞注人層及電、;轉°送層後，以如下方式在其上 單光層。將化合物5放置在真空蒸氣沉積設備的 _ 化合物e放置在另-單元中作為換 以不同速率使兩種材料蒸發而以主體材料計之2至 =比率蒸氣沉積厚度為30nm之電場發光層於電洞傳送Preparation of Compound 2-1 Compound 2 was prepared in the same manner as in Preparation 1-6 of Preparation Example 1 but using 94916 22 201109420 Compound 1-5 (5 g ' 10.37 mmol) and 2, 25, 92 mmol). ~1 (4 schwylyl phenyl (4. %, preparation of compound 2-2 '7g' δ. 29 赖 01,79. 96%). 曰 will compound 2-K4.7g, 8 for (four) and sub-disc Acid mixture 'then and then stirred under reflux. B' (5 〇 mL, hour of de,; ??? > After steaming the crane under reduced pressure, the column is separated, producing v 卩 to room temperature and mmol > 60. 〇%) 〇化口物 2 2 (2. 5g '(97 Preparation of compound 2-3 will be compound 2-2 (2.5g, 4.97mmnl, 1101), iodobenzene (2 21 curry 1), Cul (1.89 g, 9.94mmol), ', mi, 19. 89 K2C〇3 (2. 75g, iq δη and 1,2-dichlorobenzene (50mL) mixed, Rande ^ iy-«9niin〇i) ^ κ Heat to 190 ° C. After 24 t +, cool to room temperature, steam under reduced pressure and extract with EA, then distill under reduced pressure, licking its column VIII and adding hydrazine 2- 3 (2.7 g, 4.12 mmol, 82, 97%) The preparation of the compound compound 2-4 was prepared in the same manner as in Preparation Example 1. The compound was prepared in the same manner as the compound 2-3 (2.7 g, 4.13 mmol), but the compound was used to prepare the compound 2 to 4. The product was used in the next step without further purification. The compound 24 was prepared in the same manner as in the preparation of the compound of Example 1, except that the compound 2-4 (3.2 g) was used to prepare the compound 24 (1. 6 g, 2 〇 5 mm 杈 49. 98%). The compounds 1 to 31 were prepared according to the procedures of Preparation Examples 1 to 4. The j NMR and MS/FAB data of the organic electroluminescent compound thus obtained are shown in f, 9491 (5 23 201109420 Table 1 Compound ΧΗ NMR (CDC13, 200 MHz) MS/FAB measured 1 δ = 1.72 <12H, s) , 1.78 <6H, s) r 2.64(6Hr s> , 7.24-7.28(2H, m> , 7.35-7.38(3H , m> , 7.44(1H, m) , 7.55(1H, m) , 7.6K1H, m) , 7.76(1H, s) f 7·87(1Η,π〇, 7.98<2H,m> , 8.07UH , s) , 8·09(1Η, m> 554.76 554.30 2 δ = 1.48(18H, s) f 1.72(12H, s) , 1.78(6H, s), 7.24-7.28(2H/ m) , 7.35-7.38 (3H, m), 7.44(1H, o〇, 7·55(1Η, m> , 7 · 61 (1H, n〇, 7 · 76 (1H, s> , 7.87 (lH,m), 7.98 ( 2H,m) , Β·07(1Η, s) , B.09(1H, m) 638.92 638.39 3 δ = 1.72(12H, s) , 1.78(6Hf s) , 7.24-7.28(2H, m), 7.38 -7.44(6H, m>, 7.51-7.S5(9H, m>, 7.61(lHf m>, 7.76(1Η, s), 7.87-7.91(3H, m), 8.07(lHf s), 8.09 (lHf m) 678.90 678.33 4 5 = 1.72(12H, s) , 1.78(6H, s> f 7.24-7.28(2H, m) , 7.38-7.44(4H, m) , 7.55 (5H, m) , 7.61( 3rd, n), 7-76(lH, s>, 7.Θ7-7.9Κ3Η, m) , 8.04(2H, m) f 8.07(1H, s) r 8.08-8.09(3H, m> , 8.42 ( 2H, m), 8.55(2H, m> 779.02 779.36 5 δ = 1.72 <12H, s) , 1.78(6H, s> , 7.24-7.28(2H, m> , 7.38-7.44(4Hf m) , 7.55- 7.61(8H, m), 7,73<2H, m)r 7.76(lHf s) r 7.87-7.92(5Hf m), 8(4H, m>, 8.07(1H, s), 8.09(1H, m) 779.02 779.36 6 δ = 1.72(12H, s) , 1.78(6H, s) , 2.34(6H, s), 7.24-7.44(14H, m> , 7.55(1H, m) , 7.61(1H, m), 7.76 (1H, s), 7.87-7.9K3H, m), 8.07(1H, s), 8.09(1H, m) 706.95 706.36 7 δ = 1.72(12H, s) , 1.78(6H, s), 2.34(6H, s), 7.19-7.44(12H, m), 7.55(1H, a), 7.61(1H, m), 7.76(1H, s), 7.79(2H, m), 7.87-7.91(3H, m), B .07(1H, s ), 8.09(1H, m) 706.95 706.36 8 5= 1.72<12H, s) , 1.78(6H, s), 2.32{6H, s), 7.24-7.44(12H, m) , 7.55(1H, m) , 7.61-7.67(3H, a), 7.76(1H, s), 7.87-7.91(3H, m), 8.07(1H, 706.95 706.36 24 94916 201109420 s>, 8·09(1Η, m) 9 5= 1.72 (12H, s), 1.78(6H, s), 2.34(12H, s), 7.24-7.31(4H, m), 7.38-7.44(4H, m), 7.55-7.61(6H, m) , 7.76(1H , s) , 7.87-7.91(3H, m), 8.07(1H, s), 8.09(1H, m) 735.01 734.39 10 δ = 1.72(12H, s> , 1.78(6H, s> , 2.34(6H, s ), 2.59(6H, s) , 7.1 (2nd, m), 7.16(2H, m) f 7.24-7.28<2H, m) , 7.38-7.44(4H, m) , 7·55(3Η, m ), 7.61(1H, m), 7.76(1H, s>, 7.87-7.91(3H, m), 8·07(1Η, s), 8.09<1H, m) 735.01 734.39 11 δ = 1·72( 12Η, s), 1.78 (6H, s), 7·24-7·3 (6Η, 7.38-7·44(8ΗΓ 7·55(1Η, m), 7·61(1Η, tn> , 7.76(1H , s) , 7.87-7.91 (3H, m> , 8.07(1H7 s), 8.09(1H, m) 714.88 714.31 12 δ == 1.72 (12H, s) , 1.78 (6H, s> , 7.24-7.28 (2H , 7.3S-7.44 <4H, m), 7.55(1H, 7.61<1H, m>, 7.76(1H, s), 7·82-7·91(11Η, m> , 8.07(1H, s&gt ;, 8.09<1H, m) 728.92 728.32 13 δ = 1.35(18H, s> , 1.72(12H, s) , 1·78(6Η, s), 7.24-7.28(2H,, 7.37-7.44(12H, m> , 7.55 <1H, m) , 7.61(1H, m>, 7.76(1H, s> , 7.87_7.91 (3H, cn) , 8.07(1H, s) , 8.09(1H, m) 791.11 791.45 14 δ = 1·72(20Η, m) , 1.72 (OH, s> , 1.78 (6H, s), 2.74 <8H, n〇, 6.88(2H,m> , 6.98(2H,ta) f 7.15&lt ;2H, n>, 7.24-7.28(2H, m>, 7.38-7.44(4H, m) / 7.55(1H, m)f 7.61(lHf m)r 7.76(1H, s>, 7.87-7.91(3H, m)f 8.07(1H, s), 8.09(1H, m) 787.08 786.42 j 15 · • 5 = 1,72(12H, s)f 1,78(6H, s> , 7·1(2Η, n〇 , 7.24-7.28(2H, m}, 7.38-7.55(9Hf m), 7.61-7.63(3Hf m) , 7.76(1H, s) , 7.87-7.92(5Hf 780.99 780.35 25 94916 201109420 m) , 8.07(1H, s) , 8.09(1H, m) , 8.42(2H, m) 16 δ = 1·72(12Η, s) , 1.78(6H, s> , 3·83(6Η, s> , 7·05(4Η, m> , 7·24-7·28(2Η, , 7·3Β-7·44(4Η, Da), 7.55(lHf m) , 7.61(1H, m) f 7.68(4H, m), 7·76 (1Η, s> , 7.87-7.91 (3H, m) , 8.07(1H, s> , 8.09(1H, m) 738.95 738.35 17 δ = 1.72(12H, s) , 1.78(6H, s) , 7.24-7.28 (2H , bl) , 7.38-7.44(8H/ m) , 7.55(1H, m>, 7.61<lH, 7·68(4Η, m), 7·76< 1Η, s>, 7.87-7,91(3H, m) , 8.07(1R, s) , 8.09(1H, m) 814.90 814.30 18 5 = 0.25(18H, s> , 1.72(12H, s> , 1· 78(6Η, s> , 7.24-7.28(2H, m) f 7,38-7.46(8H, m) , 7.55(1H, 7·61(1Η, 7·76(1Η, s>, 7·77( 4Η, m>, 7.S7-7.91(3H, m) , 8.07(lHf s) , 8.09(lHf m) 823.26 822.41 19 δ = 1.72(12Hf s) f 1.78(6Hf s) f 7.24-7.28(2Hf m } , 7.37-7.55(39H, m> , 7.61<1H, m> , 7.76(1H, s) , 7.87-7.91(7H, m> , 8·07(1Η, s) , 8.09(1H, 1195.6 8 1194.50 20 δ = 1·72(12Η, s) , 1.78(6H, s) , 1 · 96 (4Hr m), 2.76(4H,m) f 3.06(4H,m) , 6.55 (2H,m) , 6 , 72(2H, m), 7·05-7·07(4Η, m>, 7.24-7.28(2H, m), 7.38-7.44(4H, m), 7.55(1H, 7.61(1H, m>, 7.69(1H, s), 7·87·7·91(3Η, m>, 8(1H, s>, 8.09(1Η, m) 789.06 788.41 21 δ = 1.71(12H, m) , 1.72(12H, s ), 1.78(6H, s), 2.01-2.02(18H, m), 7.24-7.28(2H, m), 7.35-7.38(3H, xn) , 7.44(1H, m) , 7.55(1H, m), 7.61 (lH, m), 7.76 (1 H, s) , 7.87(lH,m) , 7.98(2H, n) , 8.07(1H, s), 8.09(1H, m) 795.14 794.49 22 5 = 0.66(18H, s) , 7.33-7.4K6H, m ), 727.12 726.26 26 94916 201109420 7·51-7.52(10H, m) Λ 7·SI(2H, m) , 7.89-7.91<4H, m>, 8-23(lH, s), 8,25( 1H, s) 23 δ = 7·39-7.41 (4Η, 7.5-7·52(12Η, m), 7·91(4Η, s> , 7·91(ΟΗ,π〇, 7.98(2H,m) , 8·45(2Η, m> 648.86 648.10 24 δ = 7.25(2H, m) , 7.33-7.52(23H, m> , 7.58(6H, m) , 7.91(4H, s) r 7 · 91-7.94 ( 2H, m> , 8.55(2H/ tn) 825.99 825.31 25 δ = 1·72(12Η, s) , 1.78(6H, s> , 2·45(3Η, s), 7.24·7·28(3Η, m ), 7·38-7·44(4H, m), 7.51-7,55(9H, m}, 7,61(1H, m>, 7.7(1H, m>, 7.76(1H, s), 7.85 -7.87(2H, m) , 8*07(1H, s> , 8.09(1H, m) 692.93 692.34 26 δ = 1·72<12Η, s) , 1.78<6H, s> , 7·24-7.28 (2ΗΓ , 7·38-7·44(3Η, m>, 7·51-7·61(13Η, m), 7·73(2Η, m), 7·76(1Η, s), 7·87_8 (8Η, 8.07(1H, s), 8·09-8·13(2Η, m) 855.00 854.39 27 δ = 1.72 (12Hf s) , 1.78(6H, s> , 2.34(6H, s), 7.18(1H , m) , 7.24(1H, m) , 7.35-7.41 (6H, m), 7.51-7.52 (8H, m) f 7.75(lHf m) , 7.76(1H, s) r 7.91-7.97(3H, m> , 8.07(1H, s> 706.95 706.36 28 δ = 1.72(12H, s> , 1.78(6H, s) , 2.34(6Hr s> , 2.45(3H, s> , 7.18(1H, m) , 7.24-7.25 (2H, m), 7.35 (1H, m ), 7.41(3H, m>, 7.51-7.52 (8H, m), 7.7-7.75(2H, m), 7.76(1H, s), 7.85(1H, m), 7·97(1Η, m) Γ 8·07(1Η, s> 720.98 720.38 29 [ • 5 = 1.72 (12H, s) , 1.78 (6H, s) r 7.41 (5H, m), 7.51-7.52 (20H, m> , 7.61-7.63 (2H , m) , 7.69(1H, n) f 7.76(1H, s), 7.77(lHf m) f 7.83(lHf m), 7.93-7.97 (2H, m> , 8.07<1H, s) , 8·13 · 8.15(2H, 907.19 906.42 27 94916 201109420 m) 30 31 δ= S)/ l.VBtSH, — 7.2SUH, n〇, 7.41(4H, tt> , 7.S1, 7 S2(ieH, 7.63(1H) , m), 7.69-7.7(2H, »), 7.76(1H/s), 7.77UH, d83-7.S5<2H, m), 7 93(ih,( 8.07(1H, s), 8.15(1H m) 5= 1.72(12H/ s), l.78(6Hf 6.81-6.83(3H, m,, 7.03(1H, m), 7.2.728(6h, a), 7.38-7.44(4H, m) , 7.51-7.55 (9h 7.61 (lH, m>, 7.75 (lH, m>, 7·76<1Η, s), 7 87(1H, m), 8.07(1H, s), 8.09(1H, m '' 845.12 846.11 844.41 845.30 [Example 1] Manufacture of a coffee-making apparatus using an organic electroluminescent compound according to the present invention A 〇LED device was produced using the organic electroluminescent compound according to the present invention. First, 'Ultrasonic cleaning is applied to the transparent electrode IT(R) film (15 Ω/ϋ) obtained from the glass of the coffee shop (Samsung Corning) using dichloroethylene, propylene glycol and steamed water. Then, it is stored before use. In isopropyl alcohol. Then, the ΙΤ0 substrate was assembled in a substrate holder of a vacuum vapor deposition apparatus, and then 4,4',4"-叁(Ν,Ν-(2-naphthyl)__phenylamino)trimylamine ( 2-ΤΝΑΤΑ) placed in a cell of a vacuum vapor deposition apparatus, and then evacuated until the chamber has a vacuum of 106 Torr. Then, a current is applied to the unit to evaporate 2-TNATA, thereby forming on the no substrate. a hole injection layer having a thickness of 6 〇 nm. Then, n, n'_bis(α_naphthyl)_N,N,_diphenyl-4,4-diamine (NPB) is placed in a vacuum vapor deposition apparatus. In another unit, an electric current is applied to the unit to evaporate the NPB, and a hole of a thickness of 2 〇 nm is formed on the hole injection layer to form a hole of 2 〇 nm. After the layer is applied, the mono-optic layer is placed thereon in the following manner. The compound 5 is placed in the vacuum vapor deposition apparatus. The compound e is placed in the other unit as a different rate to evaporate the two materials in terms of the host material. To the ratio = vapor deposition thickness of 30nm electric field luminescent layer in the hole transmission

化合物5 後，祕沉積厚度為2Gnm之秦（8_絲啥琳）_結 為電子傳送層。然後，在蒸氣沉積厚度為） f 2mn之8-縣㈣錄iq)作為電子注人純，使用另 —真空蒸氣沉積設備形成厚度為15〇咖之A1陰極以 0LED。 & [比較例1]使用既有電場發光材料之〇LED裝置的製造 依據實施例1之程序製造0LED裝置，但在真空蒸 積設備之單元中放置DNA取代本發明之化合物作為主體^ 料0 94916 29 201109420After compound 5, the secret deposition of 2Gnm of Qin (8 _ 啥 啥 Lin) _ knot electron transport layer. Then, in the vapor deposition thickness of f 2mn, 8-county (four) recorded iq) as an electron injection pure, using another vacuum vapor deposition apparatus to form a thickness of 15 A A1 cathode to 0 LED. & [Comparative Example 1] Manufacture of an OLED device using an existing electric field luminescent material According to the procedure of Example 1, an OLED device was fabricated, but a DNA was placed in a unit of a vacuum evaporation device to replace the compound of the present invention as a host material. 94916 29 201109420

以1，000 cd/m2測量實施例1及比較例1所製造之OLED 裝置的電力效率（power efficiency)。結果示於表2。 表2 編號 主體 摻雜劑 摻雜濃度 (wt%) 電力效率 (lra/W) 色彩 1 化合物5 化合物E 3 8.2 綠色 2 化合物15 化合物E 3 8. 1 綠色 3 化合物23 化合物E 3 8. 1 綠色 4 化合物26 化合物E 3 8.0 綠色 比較例1 DNA 化合物E 3 7. 1 綠色 如表2所示，當使用於發綠光之電場發光裝置時，本 發明之有機電場發光化合物比比較例1提供更加改良之電 力效率，而維持可媲美或較佳之色純度。 【圖式簡單說明】 無 【主要元件符號說明】 益 30 94916The power efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1 was measured at 1,000 cd/m2. The results are shown in Table 2. Table 2 No. Main body dopant doping concentration (wt%) Power efficiency (lra/W) Color 1 Compound 5 Compound E 3 8.2 Green 2 Compound 15 Compound E 3 8. 1 Green 3 Compound 23 Compound E 3 8. 1 Green 4 Compound 26 Compound E 3 8.0 Green Comparative Example 1 DNA Compound E 3 7. 1 Green As shown in Table 2, when used in a green light-emitting electric field light-emitting device, the organic electroluminescent compound of the present invention is more provided than Comparative Example 1. Improved power efficiency while maintaining comparable or better color purity. [Simple description of the diagram] None [Key component symbol description] Benefit 30 94916

Claims (1)

201109420 ‘七、申請專利範圍： > 1.一種化學式（1)所示之有機電場發光化合物： r2201109420 ‘7. Patent application scope: > 1. An organic electroluminescent compound of the formula (1): r2 式中 匕至R5獨立表示氫、氘、i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、與一個或多個經取代或未經取代之（C3-C30)環烷基 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-員雜環烷基、與一個或多個經取代或未經取代之芳香 環稠合之5-至7-員雜環烷基、經取代或未經取代之 (C3-C30)環烷基、與一個或多個經取代或未經取代之芳 香環稠合之（C3-C30)環烷基、氰基、NRuRu、BR〗3Ri4、 PR15R16、P(=〇)RnRi8[式中Ru至Ru獨立表示經取代或未 經取代之（Cl -C30)烧基、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]、 RaRbReSi-[式中Ra、Rb及Re獨立表示經取代或未經取代 之（C1-C30)烷基或者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（C1-C30)烷 基、RdY-[式中Y表示S或〇，及Rd表示經取代或未經 31 94916 201109420 取代之（C1-C30)烷基或者經取代或未經取代之（C6_C3〇) 方基]、經取代或未經取代之（C2〜C30)烯基、經取代或Wherein 匕 to R5 independently represent hydrogen, deuterium, i, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, and one or more Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl fused, substituted Or unsubstituted 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused to one or more substituted or unsubstituted aromatic rings, substituted or unsubstituted (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused to one or more substituted or unsubstituted aromatic rings, cyano, NRuRu, BR 3Ri4, PR15R16, P(= 〇)RnRi8 [wherein Ru to Ru independently represents a substituted or unsubstituted (Cl-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (C3 -C30)heteroaryl], RaRbReSi-[wherein Ra, Rb and Re independently represent a substituted or unsubstituted (C1-C30) alkyl group or a substituted or unsubstituted (C6-C30) aryl group] Substituted or unsubstituted (C6-C30) aryl (C1- C30) alkyl, RdY-[wherein Y represents S or hydrazine, and Rd represents (C1-C30)alkyl or substituted or unsubstituted (C6_C3〇) aryl group substituted or not substituted by 31 94916 201109420 Substituted or unsubstituted (C2~C30) alkenyl, substituted or 未經取代之（C2-C30)炔基、 ^21Unsubstituted (C2-C30) alkynyl group, ^21 ，但排除R4及Rs同時為氫或氘的情形； 、-(R31 )C = C(R32)_、 、-P(R36)-、 W’X’Y 及 Z 獨立表示-(CR31R32)m--N(R33)---s---〇---Si(R34)(R35)、 - P(=0)(R37)---c(=0)-或-B(R38)〜； R21至R23及Rsi至R38係與Ri至R3相同，其中r31至 R38各可經由具有或不具有稠合環之（C3_C3〇)伸烷基或 (C3-C30)伸烯基連結至相鄰取代基以形成脂環或單環 或多環之芳香環； 該雜環烷基及雜芳基可含有選自B、N、〇、s、 P(=〇)、Si及p之一個或多個雜原子；以及 m表示〇，1或2之整數。 2.如申請專利範圍第1項所述之有機電場發光化合物，其 中Ri至R3獨立表示氫、氘、鹵素、經取代或未經取代 之（C卜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、經取代或未經取 代之（C3-C30)環烷基、經取代或未經取代之金剛烷基、 NKnRK [式中Rn及R12獨立表示經取代或未經取代之 32 94916 201109420 (C1-C30)烧基、經取代或未經取代之（C6-C30)芳基、或 者經取代或未經取代之（C3-C30)雜芳基]或 R R R S i [式中pa、及rc獨立表示經取代或未經取代 之（C1-C30)烷基或者經取代或未經取代之（C6_C3〇)芳 基]，且匕及^可獨立表示經取代或未經取代之（C卜C30) 烷基、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-C3Q)環烷基稠合之經取代 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_員雜環 烷基、與一個或多個經取代或未經取代之芳香環稠合之 5至7、員雜裱烷基、經取代或未經取代之（C3_c3〇)環 烷基、或者與一個或多個經取代或未經取代之芳香環稠 合之（C3-C30)環烧基。 •如申明專利圍第1或2項所述之有機電場發光化合 物’其中及心至^的取代基可進一步經一個 或多個選自亂、鹵素、具有或不具有鹵素取代基之 .C30)絲、⑽-⑽）芳基、具有或不具有⑽―_ 芳基取代基之⑽―G3G)⑽基、5-至Η雜環烧基、 個芳香至卜員雜環烧基、 (C3-C30)環炫基、與一個或客 ro # 夕個方香環稠合之（C6-C30) 每炫基、三（Cl-C30)烷基矽 ^ 、 從基、二（C1-C30)烷基 (C6-C30)芳基石夕烧基、三 其雄里，6〜C3〇)芳基矽烷基、金剛烷 基、（C7-C30)雙ί哀炫基、（〇 ^ ^ ^ ^ NID D C30)烯基、（C2-C30)炔基、 fl基、味°坐基、NR41R42、邱4 u 3 44、PR45R46、P(=〇)r47r48[式[s 94916 33 201109420 中〜至R48獨立表示經取代或未經取代之（Ci_c3〇)烧 基、經取代或未經取代之（C6-C30)芳基或者經取代或未 經取代之（C3-C30)雜芳基]、（C6-C30)芳基（ci-C3〇)炫 基、（C1-C30)烧基（C6-C30)芳基、（C1-C30)烧氧基、 (C1-C30)烧基硫基、（C6-C30)芳氧基、（C6_C3〇)芳硫 基、（C1-C30)烧氧基羰基、（C1-C30)院基羰基、（C6-C30) 芳基羰基、（C6-C30)芳氧基羰基、（ci—C30)烷氧基羰氧 基、（C1-C30)烷基羰氧基、（C6-C30)芳基羰氧基、 (C6-C30)芳氧基羰氧基、羧基、硝基及羥基所組成族群 之取代基取代；或連結至相鄰取代基以形成環。 4.如申請專利範圍第3項所述之有機電場發光化合物，其 係選自下述化合物： 94916 34 201109420, except that R4 and Rs are both hydrogen or helium; , -(R31)C = C(R32)_, , -P(R36)-, W'X'Y and Z are independently represented -(CR31R32)m- -N(R33)---s---〇---Si(R34)(R35), -P(=0)(R37)---c(=0)- or -B(R38)~; R21 to R23 and Rsi to R38 are the same as Ri to R3, wherein each of r31 to R38 may be bonded to an adjacent substituent via a (C3_C3〇)alkylene group or a (C3-C30)alkylene group with or without a fused ring. a group to form an alicyclic or monocyclic or polycyclic aromatic ring; the heterocycloalkyl and heteroaryl group may contain one or more selected from the group consisting of B, N, hydrazine, s, P (= 〇), Si, and p a hetero atom; and m represents an integer of 〇, 1 or 2. 2. The organic electroluminescent compound according to claim 1, wherein Ri to R3 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C, C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted adamantane , NKnRK [wherein Rn and R12 independently represent substituted or unsubstituted 32 94916 201109420 (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted Substituted (C3-C30)heteroaryl] or RRRS i [wherein, pa and rc independently represent substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6_C3〇) aryl And / and independently represent a substituted or unsubstituted (C, C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, and one or more substituted or unsubstituted Substituted (C3-C3Q)cycloalkyl fused substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl, taken Or unsubstituted 5_ to 7-membered heterocycloalkyl, 5 to 7, fused to a substituted or unsubstituted aromatic ring, substituted or unsubstituted (C3_c3〇)cycloalkyl or a (C3-C30)cycloalkyl group fused to one or more substituted or unsubstituted aromatic rings. • The substituent of the organic electroluminescent compound 'incorporating the core to the above, as defined in claim 1 or 2, may further be substituted by one or more substituents selected from chaotic, halogen, with or without a halogen substituent. C30) Silk, (10)-(10)) aryl, (10)-G3G) (10) group with or without (10)--aryl substituent, 5- to fluorene heterocyclic group, aromatic to heterocyclic alkyl group, (C3- C30) cyclodextrin, fused to one or the guest ro # 夕方香 (C6-C30) per leuco, tri(Cl-C30)alkyl 矽^, benzyl, bis(C1-C30)alkyl ( C6-C30) aryl stone sulphur base, Sanqixiong, 6~C3 〇) aryl decyl, adamantyl, (C7-C30) shuangqing, (〇^ ^ ^ ^ NID D C30) Alkenyl group, (C2-C30) alkynyl group, fl group, taste group, NR41R42, Qiu 4 u 3 44, PR45R46, P(=〇)r47r48 [Formula [s 94916 33 201109420]~ to R48 independently represent substituted Or unsubstituted (Ci_c3〇)alkyl, substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (C3-C30)heteroaryl], (C6-C30) aryl Base (ci-C3〇) dazzle, (C1-C30) alkyl (C 6-C30) aryl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6_C3〇) arylthio, (C1-C30) oxygenated Carbonyl group, (C1-C30) carbonyl group, (C6-C30) arylcarbonyl group, (C6-C30) aryloxycarbonyl group, (ci-C30) alkoxycarbonyloxy group, (C1-C30) alkyl group Substituting a substituent of a group consisting of a carbonyloxy group, a (C6-C30) arylcarbonyloxy group, a (C6-C30) aryloxycarbonyloxy group, a carboxyl group, a nitro group, and a hydroxyl group; or linking to an adjacent substituent to form ring. 4. The organic electroluminescent compound according to claim 3, which is selected from the group consisting of the following compounds: 94916 34 201109420 35 94916 20110942035 94916 201109420 5. —種有機電場發光裝置，包括如申請專利範圍第1至4 項中任一項所述之有機電場發光化合物。 6. 如申請專利範圍第5項所述之有機電場發光裝置，其包 括第電極，第二電極；以及插置在該第一電極與該第 一電極間之一層或多層有機層，其中有機層包括如申請 f利範圍第1至4中項任—項所述之-種或多種有機電 場發光化合物及選自化學式（2)或（3)所示之化合物之 一種或多種摻雜劑： 94916 36 2011094205. An organic electric field illuminating device comprising the organic electroluminescent compound according to any one of claims 1 to 4. 6. The organic electric field light-emitting device according to claim 5, comprising: a first electrode, a second electrode; and one or more organic layers interposed between the first electrode and the first electrode, wherein the organic layer And the one or more organic electroluminescent compounds and the one or more dopants selected from the compounds represented by the chemical formula (2) or (3), as described in the claims 1 to 4: 94916 36 201109420 式中 Arn及Am獨立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-C30)芳基胺基、（cl_C3〇)烷基胺基、經取代或未經 取代之5-至7-員雜環烷基、與一個或多個經取代或未 經取代之芳香環祠合之5-至7-員雜環烷基、經取代或 未經取代之（C3-C30)環烷基、或與一個或多個經取代或 未經取代之芳香環铜合之（C3_C3〇)環烷基；或人^與 An2經由具有或不具有稠合環之（C3-C30)伸烷基或 (C3-C30)伸埽基連結以形成脂環或單環或多環之芳香 孩， Ari3表示經取代或未經取代之（C6-C30)芳基、經取 代或未經取代之（C4〜C30)雜芳基或選自下述結構之取 代基（當c為1時）：Wherein Arn and Am independently represent substituted or unsubstituted (C-C3〇) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C4-C30) a heteroaryl group, a substituted or unsubstituted (C6-C30) arylamino group, a (cl_C3〇)alkylamino group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, and a Or a substituted or unsubstituted aromatic ring of a 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or substituted with one or more Or an unsubstituted aromatic ring copper (C3_C3〇)cycloalkyl; or human and An2 linked via a (C3-C30) alkyl or (C3-C30) thiol group with or without a fused ring To form an alicyclic or monocyclic or polycyclic aromatic child, Ari3 represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (C4 to C30) heteroaryl group or selected from the group consisting of Substituents for the structure (when c is 1): .Am‘七翁 Rin2Rffl3.Am ‘七翁 Rin2Rffl3 94916 37 201109420 Am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)伸雜芳基或選自下述結構 之取代基（當c為2時）：94916 37 201109420 Am represents substituted or unsubstituted (C6-C30) extended aryl, substituted or unsubstituted (C4-C30) heteroaryl or a substituent selected from the following structure (when c is 2 o'clock): Aru及Aris獨立表示經取代或未經取代之（C6-C3〇；) 伸芳基、經取代或未經取代之（C4-C30)伸雜芳基； Run至Ri。3獨立表示氫、氘、經取代或未經取代之 (C1-C30)烧基或者經取代或未經取代之（C6-C30)芳基. d表示1至4之整數；以及 e表示0或1之整數。 7.如申請專利範圍第6項所述之有機電場發光骏置，其中 亥有機層包括選自由芳基胺化合物及苯乙烯基芳基胺 s物所組成群族之—種或多種化合物。 =申π專利範圍第6項所述之有機電場發光裝置，其中 t機層進步包括選自第1族之有機金屬，第2族， 素所Γ期和第5周期過渡金屬，鋼系金屬及k過渡元 9·如申種金屬或錯合物化合物。 -:6項所述之有機電場發光袭置，其係 包括發出置，其中該有機層進一步 層。 光之一層或多層有機電場發光 94916 38 201109420 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：Aru and Aris independently represent substituted or unsubstituted (C6-C3〇;) aryl, substituted or unsubstituted (C4-C30) heteroaryl; Run to Ri. 3 independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl. d represents an integer from 1 to 4; and e represents 0 or An integer of 1. 7. The organic electric field illuminating device according to claim 6, wherein the organic layer comprises one or more compounds selected from the group consisting of arylamine compounds and styrylarylamines. The organic electric field illuminating device of the sixth aspect of the invention, wherein the t-layer progress comprises an organometallic selected from the group 1, the second group, the transition period of the prime period and the fifth period transition metal, the steel metal and k transition element 9 such as the application of metal or complex compounds. -: The organic electric field illuminating according to item 6, which comprises emitting a layer, wherein the organic layer is further layered. Light one layer or multiple layers of organic electric field illumination 94916 38 201109420 IV. Designated representative map: There is no pattern in this case (1) The representative representative figure of this case is: (). (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 2 949162 94916
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