TW201710263A - Organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Organic electroluminescent compounds and organic electroluminescent device comprising the same Download PDF

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TW201710263A
TW201710263A TW105122501A TW105122501A TW201710263A TW 201710263 A TW201710263 A TW 201710263A TW 105122501 A TW105122501 A TW 105122501A TW 105122501 A TW105122501 A TW 105122501A TW 201710263 A TW201710263 A TW 201710263A
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金榮光
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羅門哈斯電子材料韓國公司
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Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure is effective in preparing an organic electroluminescent device having a remarkably improved lifespan.

Description

有機電致發光化合物及包括其的有機電致發光裝置 Organic electroluminescent compound and organic electroluminescent device therewith

本發明是有關於一種有機電致發光化合物及一種包括其的有機電致發光裝置。 The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.

電致發光(EL)裝置為自身發光裝置，其優點在於其提供較寬視角、較高對比度及較快反應時間。有機EL裝置最初由Eastman Kodak藉由使用小芳族二胺分子及鋁錯合物作為用於形成發光層之材料而開發[Appl.Phys.Lett.51,913,1987]。 Electroluminescent (EL) devices are self-illuminating devices that have the advantage of providing a wider viewing angle, higher contrast, and faster response times. The organic EL device was originally developed by Eastman Kodak by using a small aromatic diamine molecule and an aluminum complex as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

當將電力施加至有機發光材料時有機EL裝置(OLED)將電能轉化成光。一般而言，有機EL裝置具有包括陽極、陰極及安置於陽極與陰極之間的有機層之結構。有機EL裝置之有機層包括電洞注入層、電洞傳輸層、電子阻擋層、發光層(包括主體材料及摻雜材料)、電子緩衝層、電洞阻擋層、電子傳輸層、電子注入層等。視其功能而定，用於形成有機層之材料可分類為電洞注入材料、電洞傳輸材料、電子阻擋材料、發光材料、電子緩衝材料、電洞阻擋材料、電子傳輸材料、電子注入材料等。當將電壓施加至有機EL裝置 時，電洞及電子分別自陽極及陰極注入至發光層。具有較高能量之激子藉由電洞與電子之間的重組形成，能量使有機發光化合物處於激發態，且激發態之衰減引起能量位準弛豫至基態，伴隨光發射。 An organic EL device (OLED) converts electrical energy into light when electric power is applied to the organic light emitting material. In general, an organic EL device has a structure including an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer of the organic EL device includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer (including a host material and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. . Depending on its function, the materials used to form the organic layer can be classified into hole injection materials, hole transmission materials, electron blocking materials, luminescent materials, electronic buffer materials, hole blocking materials, electron transport materials, electron injecting materials, and the like. . When a voltage is applied to the organic EL device At the time, the holes and electrons are injected from the anode and the cathode to the light-emitting layer, respectively. Excitons with higher energy are formed by recombination between the holes and the electrons, the energy causes the organic luminescent compound to be in an excited state, and the attenuation of the excited state causes the energy level to relax to the ground state, accompanied by light emission.

決定有機EL裝置的發光效率的最重要因素為發光材料。發光材料需要具有較高量子效率、較高電子遷移率及較高電洞遷移率。此外，由發光材料形成之發光層需要為均勻且穩定的。視藉由光發射觀測之顏色而定，發光材料可歸類為發射藍光、發射綠光或發射紅光之材料，且可另外包含發射黃光或發射橙光之材料。此外，發光材料可根據其功能歸類為主體材料及摻雜材料。近來，迫切需要開發提供高效及長久壽命之OLED。特定言之，考慮到EL需要中等或大型尺寸之OLED面板，必須迫切開發與習知材料相比顯示較好效能的材料。為了達成開發，以固態形式起溶劑作用且轉移能量之主體材料應具有較高純度及適當分子量以便在真空中沈積。另外，主體材料應具有較高玻璃轉化溫度及較高熱分解溫度以確保熱穩定性；較高電化學穩定性以具有長久壽命；易於製備非晶形薄膜；及對鄰近層材料之良好黏著性。此外，主體材料不應移動至鄰近層。 The most important factor determining the luminous efficiency of an organic EL device is a luminescent material. Luminescent materials are required to have higher quantum efficiency, higher electron mobility, and higher hole mobility. Further, the light-emitting layer formed of the luminescent material needs to be uniform and stable. Depending on the color observed by light emission, the luminescent material may be classified as a material that emits blue light, emits green light, or emits red light, and may additionally contain a material that emits yellow light or emits orange light. In addition, the luminescent material can be classified into a host material and a dopant material according to its function. Recently, there is an urgent need to develop an OLED that provides high efficiency and long life. In particular, considering that ELs require medium or large-sized OLED panels, materials that exhibit better performance than conventional materials must be urgently developed. In order to achieve development, the host material which acts as a solvent in a solid form and transfers energy should have a higher purity and a suitable molecular weight for deposition in a vacuum. In addition, the host material should have a higher glass transition temperature and a higher thermal decomposition temperature to ensure thermal stability; higher electrochemical stability to have a long life; easy to prepare an amorphous film; and good adhesion to adjacent layer materials. In addition, the host material should not be moved to adjacent layers.

韓國專利特許公開申請案第10-2015-0021861號揭示具有稠環結構之作為發光層材料之芳族衍生物。然而，需要在改良有機電致發光裝置之光發射效率及熱穩定性方面有效的新穎有機電致發光化合物。 Korean Patent Application Laid-Open No. 10-2015-0021861 discloses an aromatic derivative having a fused ring structure as a material of a light-emitting layer. However, there is a need for novel organic electroluminescent compounds that are effective in improving the light emission efficiency and thermal stability of organic electroluminescent devices.

由於發現與習知有機發光化合物相比可提供具有優良效能之有機電致發光裝置的新穎化合物的研究，本發 明人發現本發明之化合物可提供具有改良之壽命的有機電致發光裝置。 The present invention has been found to provide a novel compound capable of providing an organic electroluminescent device having excellent performance as compared with a conventional organic light-emitting compound. The compounds of the present invention have been found to provide an organic electroluminescent device having an improved lifetime.

本發明之目標為提供一種有機電致發光化合物，其在製備具有顯著改良之壽命的有機電致發光裝置方面有效。 It is an object of the present invention to provide an organic electroluminescent compound which is effective in the preparation of an organic electroluminescent device having a significantly improved lifetime.

由於解決上文所描述的問題之認真研究，本發明人發現以上目標可藉由由下式1表示之有機電致發光化合物實現且開始完成本發明。 The present inventors have found that the above object can be attained by the organic electroluminescent compound represented by the following formula 1 and the completion of the present invention, as a result of careful study of the problems described above.

其中X表示-O-、-S-或-NR9-；La表示單鍵、經取代或未經取代之(C6-C30)芳基或經取代或未經取代之(3至30員)雜芳基；Ma表示經取代或未經取代之(C6-C30)芳基或經取代或未經取代之(3至30員)雜芳基；A及B各獨立地表示經取代或未經取代之苯基或經取代或未經取代之萘基；R1至R9各獨立地表示氫、氘、鹵素、氰基、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(3至30員)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(C1-C30)烷氧基、經取代或未經取代之三(C1-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(C1-C30)烷基二(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單-或二-(C1-C30)烷基胺基、經取代或未經取代之單-或二-(C6-C30)芳基胺基或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基；或可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C30)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自氮、氧及硫之雜原子置換；及所述雜芳基含有至少一個選自B、N、O、S、Si及P之雜原子。 Wherein X represents -O-, -S- or -NR 9 -; La represents a single bond, a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3 to 30 member) Aryl; Ma represents substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3 to 30 membered) heteroaryl; A and B each independently represent substituted or unsubstituted a phenyl group or a substituted or unsubstituted naphthyl group; R 1 to R 9 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or Unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted Substituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkyldecane, substituted or unsubstituted bis(C1-C30)alkyl (C6-C30) aryl Alkyl, substituted or unsubstituted (C1-C30)alkyl di(C6-C30)aryldecyl, substituted or unsubstituted tris(C6-C30)aryldecyl, substituted or substituted Unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamine a substituted or unsubstituted (C1-C30)alkyl (C6-C30) arylamino group; or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C30), monocyclic ring. Or a polycyclic, alicyclic or aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; and the heteroaryl group containing at least one selected from the group consisting of B, N, O, S , Si and P heteroatoms.

當其在發光層中使用時，本發明之有機電致發光化合物可與習知有機發光化合物相比，提供顯著改良之有機電致發光裝置壽命。 When used in a light-emitting layer, the organic electroluminescent compound of the present invention provides a significantly improved lifetime of an organic electroluminescent device as compared to conventional organic light-emitting compounds.

本發明的實施例Embodiment of the present invention

在下文中，將詳細描述本發明。然而，以下描述打算解釋本發明，且不意謂以任何方式限制本發明之範疇。 Hereinafter, the present invention will be described in detail. However, the following description is intended to be illustrative of the invention and is not intended to limit the scope of the invention in any way.

本發明提供以上式1之有機電致發光化合物、包括其之有機電致發光材料及包括所述材料之有機電致發光裝置。 The present invention provides an organic electroluminescent compound of the above formula 1, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the same.

本發明之式1化合物可由下式2表示： The compound of the formula 1 of the present invention can be represented by the following formula 2:

其中X、La、Ma及R1至R9如在以上式1中所定義；R10至R15各獨立地表示氫、氘、鹵素、氰基、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(3至30員)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(C1-C30)烷氧基、經取代或未經取代之三(C1-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(C1-C30)烷基二(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單-或二-(C1-C30)烷基胺基、經取代或未經取代之單-或二-(C6-C30)芳基胺基或經取代或未經取代之(C1-C30)烷基(C6-C30)芳基胺基；或可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C30)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自氮、氧及硫之雜原子置換；及所述雜芳基含有至少一個選自B、N、O、S、Si及P之雜原子。 Wherein X, La, Ma and R 1 to R 9 are as defined in the above formula 1; R 10 to R 15 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30). Alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C3-C30) naphthenic (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkyldecane, substituted or unsubstituted bis(C1-C30)alkane, substituted or unsubstituted (C6-C30) aryl decyl, substituted or unsubstituted (C1-C30) alkyl bis(C6-C30) aryl decyl, substituted or unsubstituted tris(C6-C30) aryl Alkyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino or substituted Or unsubstituted (C1-C30)alkyl (C6-C30) arylamine; or may be bonded to adjacent substituents to form substituted or unsubstituted (C3-C30), monocyclic or polycyclic, An alicyclic ring or an aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; and the heteroaryl group Having at least one hetero atom selected from B, N, O, S, Si and P of.

在式1中，La可較佳表示單鍵、經取代或未經取代之(C6-C20)芳基或經取代或未經取代之(3至20員)雜芳 基；且更佳表示單鍵、未經取代之(C6-C12)芳基或未經取代之三嗪基或吡啶基。 In Formula 1, La may preferably represent a single bond, a substituted or unsubstituted (C6-C20) aryl group or a substituted or unsubstituted (3 to 20 member) heteroaryl group. More preferably, it represents a single bond, an unsubstituted (C6-C12) aryl group or an unsubstituted triazinyl group or a pyridyl group.

在式1中，Ma可較佳表示經取代或未經取代之(C6-C20)芳基或經取代或未經取代之(3至20員)雜芳基；且更佳表示經取代或未經取代之(C6-C12)芳基或未經取代或經(C6-C20)芳基取代之苯基、聯三苯、三嗪基、吡啶基、喹啉基、喹唑啉基、嘧啶基或喹喏啉基。 In Formula 1, Ma may preferably represent a substituted or unsubstituted (C6-C20) aryl group or a substituted or unsubstituted (3 to 20 membered) heteroaryl group; and more preferably substituted or not Substituted (C6-C12) aryl or unsubstituted or substituted by (C6-C20) aryl, phenyl, terphenyl, triazinyl, pyridyl, quinolinyl, quinazolinyl, pyrimidinyl Or quinoxalinyl.

在式1中，R1至R9各獨立地可較佳表示氫、氘、經取代或未經取代之(C1-C20)烷基、經取代或未經取代之(C6-C20)芳基、經取代或未經取代之(3至20員)雜芳基、經取代或未經取代之(C3-C20)環烷基、經取代或未經取代之(C1-C20)烷氧基、經取代或未經取代之三(C1-C20)烷基矽烷基、經取代或未經取代之二(C1-C20)烷基(C6-C20)芳基矽烷基、經取代或未經取代之(C1-C20)烷基二(C6-C20)芳基矽烷基、經取代或未經取代之三(C6-C20)芳基矽烷基、經取代或未經取代之單-或二-(C1-C20)烷基胺基、經取代或未經取代之單-或二-(C6-C20)芳基胺基或經取代或未經取代之(C1-C20)烷基(C6-C20)芳基胺基；或可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C20)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自氮、氧及硫之雜原子置換；所述雜芳基含有至少一個選自B、N、O、S、Si及P之雜原子。 In Formula 1, R 1 to R 9 each independently preferably represent hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C20) aryl. Substituted or unsubstituted (3 to 20 membered) heteroaryl, substituted or unsubstituted (C3-C20)cycloalkyl, substituted or unsubstituted (C1-C20) alkoxy, Substituted or unsubstituted tri(C1-C20)alkyldecane, substituted or unsubstituted bis(C1-C20)alkyl(C6-C20)aryldecyl, substituted or unsubstituted (C1-C20)alkyl di(C6-C20)aryldecyl, substituted or unsubstituted tris(C6-C20)aryldecyl, substituted or unsubstituted mono- or di-(C1 -C20) alkylamino, substituted or unsubstituted mono- or di-(C6-C20) arylamino group or substituted or unsubstituted (C1-C20) alkyl (C6-C20) aryl Or an alkyl group; or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C20), monocyclic or polycyclic, alicyclic or aromatic ring, the carbon atom of which may be selected from at least one Heteroatoms of nitrogen, oxygen and sulfur; the heteroaryl group contains at least one hetero atom selected from the group consisting of B, N, O, S, Si and P.

本文中，「(C1-C30)烷基」指示具有1至30，較佳1至20，且更佳1至10個碳原子之直鏈或分支鏈烷基，且包含甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基等。「(C2-C30)烯基」指示具有2至30，較佳2至20，且 更佳2至10個碳原子之直鏈或分支鏈烯基，且包含乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等。「(C2-C30)炔基」指示具有2至30，較佳2至20，且更佳2至10個碳原子之直鏈或分支鏈炔基，且包含乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等。本文中，「(C1-C30)烷氧基」指示具有1至30，較佳1至20，且更佳1至10個碳原子之直鏈或分支鏈烷氧基，且包含甲氧基、乙氧基、丙氧基、異丙氧基、1-乙基丙氧基等。本文中，「(C3-C30)環烷基」指示具有3至30，較佳3至20，更佳3至7個環主鏈碳原子之單環或多環烴。環烷基包含環丙基、環丁基、環戊基、環己基等。本文中，「(3至7員)雜環烷基」指示具有3至7個環主鏈原子，包含至少一個選自B、N、O、S、Si及P，較佳O、S及N之雜原子之環烷基，且包含吡咯啶、硫、四氫哌喃等。本文中，「(C6-C30)(伸)芳基」指示衍生自芳族烴之具有6至30，較佳6至20，更佳6至15個環主鏈碳原子的單環類型或稠環類型的基團。芳基包含苯基、聯苯、聯三苯、萘基、茀基、菲基、蒽基、茚基、聯伸三苯基、芘基、并四苯基、苝基、艸快基、稠四苯基、茀蒽基等。本文中，「(3至30員)(伸)雜芳基」指示具有3至30，較佳3至20，更佳3至15個環主鏈原子，包含至少一個，較佳1至4個選自由B、N、O、S、Si及P組成之群的雜原子的芳基；可為單環，或與至少一個苯環縮合之稠環；可為部分飽和；可為藉由經由單鍵將至少一個雜芳基或芳基鍵聯至雜芳基形成之基團；及包含單環類型的雜芳基，諸如呋喃基、噻吩基、吡咯基、咪唑基、吡唑 基、噻唑基、噻二唑基、異噻唑基、異噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、三唑基、四唑基、呋呫基、吡啶基、吡嗪基、嘧啶基、噠嗪基等；及稠環類型的雜芳基，諸如苯并呋喃基、苯并噻吩基、異苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并異噻唑基、苯并異噁唑基、苯并噁唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異喹啉基、啉基、喹唑啉基、喹喏啉基、咔唑基、啡噁嗪基、啡啶基、苯并間二氧雜環戊烯基等。此外，「鹵素」包含F、Cl、Br及I。 Herein, "(C1-C30)alkyl" means a straight or branched alkyl group having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes a methyl group, an ethyl group, N-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. "(C2-C30)alkenyl" means a straight or branched alkenyl group having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, and includes a vinyl group, a 1-propenyl group, and 2 a propylene group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 2-methylbut-2-enyl group, or the like. "(C2-C30)alkynyl" means a straight-chain or branched alkynyl group having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, and includes an ethynyl group, a 1-propynyl group, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. Herein, "(C1-C30) alkoxy" means a straight-chain or branched alkoxy group having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes a methoxy group, Ethoxy, propoxy, isopropoxy, 1-ethylpropoxy and the like. Herein, "(C3-C30)cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, more preferably 3 to 7 ring main chain carbon atoms. The cycloalkyl group includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like. Herein, the "(3 to 7 membered) heterocycloalkyl group" has 3 to 7 ring main chain atoms, and at least one member selected from the group consisting of B, N, O, S, Si and P, preferably O, S and N a heteroatom cycloalkyl group, and includes pyrrolidine, sulfur , tetrahydropyran and the like. Herein, "(C6-C30) (extended) aryl" means a monocyclic type or a thick group derived from an aromatic hydrocarbon having 6 to 30, preferably 6 to 20, more preferably 6 to 15 ring main chain carbon atoms. A ring type group. The aryl group includes phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, anthryl, fluorenyl, terphenyl, fluorenyl, tetraphenyl, fluorenyl, fluorenyl, condensed Phenyl, fluorenyl and the like. As used herein, "(3 to 30 member) (extended) heteroaryl"" has from 3 to 30, preferably from 3 to 20, more preferably from 3 to 15 ring backbone atoms, and includes at least one, preferably from 1 to 4 An aryl group selected from the group consisting of B, N, O, S, Si, and P; may be a single ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; a bond linking at least one heteroaryl or aryl group to a heteroaryl group; and a heteroaryl group containing a monocyclic type such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl , thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazolyl, pyridyl, pyrazinyl , pyrimidinyl, pyridazinyl, etc.; and fused ring type heteroaryl, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazole , benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, quinolyl, Isoquinolinyl, A phenyl group, a quinazolinyl group, a quinoxalinyl group, a carbazolyl group, a phenoxazinyl group, a phenanthryl group, a benzodioxolyl group, and the like. Further, "halogen" includes F, Cl, Br, and I.

此外，本文中，表述「經取代或未經取代」中之「經取代」意謂特定官能基中之氫原子經另一原子或基團(即取代基)置換。在式1及式2中，經取代之(C1-C30)烷基、經取代之(C1-C30)烷氧基、經取代之(C3-C30)環烷基、經取代之(C6-C30)芳基、經取代之(3至30員)雜芳基及經取代之(C3-C30)單環或多環脂環族環或芳族環之取代基各獨立地為選自由以下組成之群的至少一者：氘、鹵素、氰基、羧基、硝基、羥基、(C1-C30)烷基、鹵基(C1-C30)烷基、(C2-C30)烯基、(C2-C30)炔基、(C1-C30)烷氧基、(C1-C30)烷硫基、(C3-C30)環烷基、(C3-C30)環烯基、(3至7員)雜環烷基、(C6-C30)芳氧基、(C6-C30)芳基硫基、經(C6-C30)芳基取代或未經取代之(5至30員)雜芳基、經(5至30員)雜芳基取代或未經取代之(C6-C30)芳基、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、(C1-C30)烷基二(C6-C30)芳基矽烷基、胺基、單-或二-(C1-C30)烷基胺基、單-或二-(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30) 芳基胺基、(C1-C30)烷基羰基、(C1-C30)烷氧羰基、(C6-C30)芳基羰基、二(C6-C30)芳基硼基、二(C1-C30)烷基硼基、(C1-C30)烷基(C6-C30)芳基硼基、(C6-C30)芳基(C1-C30)烷基及(C1-C30)烷基(C6-C30)芳基。 Further, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is substituted with another atom or a group (i.e., a substituent). In Formula 1 and Formula 2, substituted (C1-C30) alkyl, substituted (C1-C30) alkoxy, substituted (C3-C30) cycloalkyl, substituted (C6-C30) The aryl, substituted (3 to 30 membered) heteroaryl and substituted (C3-C30) monocyclic or polycyclic alicyclic or aromatic ring substituents are each independently selected from the group consisting of At least one of the group: hydrazine, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30) alkyl, halo (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30 Alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3 to 7 membered)heterocycloalkyl , (C6-C30) aryloxy, (C6-C30) arylthio, substituted or unsubstituted (5 to 30 membered) heteroaryl, (5 to 30 members) (heteroaryl substituted or unsubstituted (C6-C30) aryl, tri(C1-C30)alkyldecyl, tris(C6-C30)aryldecyl, di(C1-C30)alkyl (C6) -C30) aryl decyl, (C1-C30)alkylbis(C6-C30)aryldecyl, amine, mono- or di-(C1-C30)alkylamino, mono- or di-( C6-C30) arylamine, (C1-C30)alkyl (C6-C30) Arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, bis(C6-C30)arylboryl,di(C1-C30)alkane Boronyl, (C1-C30)alkyl (C6-C30) aryl boron, (C6-C30) aryl (C1-C30) alkyl and (C1-C30) alkyl (C6-C30) aryl .

更確切而言，本發明之式1有機電致發光化合物包含以下，但不限於此： More specifically, the organic electroluminescent compound of the formula 1 of the present invention comprises the following, but is not limited thereto:

本發明之有機電致發光化合物可藉由熟習此項技術者已知之合成方法製備。 The organic electroluminescent compounds of the present invention can be prepared by synthetic methods known to those skilled in the art.

此外，本發明提供包括式1之有機電致發光化合物的有機電致發光材料，及包括所述材料之有機電致發光裝置。 Further, the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of Formula 1, and an organic electroluminescent device comprising the same.

材料可僅由本發明之有機電致發光化合物組成。或者，除本發明之化合物以外，材料可進一步包括已包括在有機電致發光材料中的習知化合物。 The material may consist solely of the organic electroluminescent compound of the invention. Alternatively, in addition to the compound of the present invention, the material may further include a conventional compound which has been included in the organic electroluminescent material.

本發明之有機電致發光裝置可包括第一電極、第二電極及至少一個安置於第一電極與第二電極之間的有機層。有機層可包括至少一種式1有機電致發光化合物。 The organic electroluminescent device of the present invention may include a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode. The organic layer may include at least one organic electroluminescent compound of Formula 1.

第一電極及第二電極中之一者可為陽極，且另一者可為陰極。有機層可包括發光層，且可進一步包括至少一個選自以下之層：電洞注入層、電洞傳輸層、電子傳輸層、電子緩衝層、電子注入層、夾層、電洞阻擋層及電子阻擋層。 One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer may include a light emitting layer, and may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole barrier layer, and an electron blocking layer. Floor.

本發明之式1之有機電致發光化合物可包括於發光層中作為主體材料。較佳地，發光層可進一步包括至少一種摻雜劑，且若需要，可另外包括除本發明之式1之有機電 致發光化合物以外的化合物作為第二主體材料。 The organic electroluminescent compound of the formula 1 of the present invention may be included in the light-emitting layer as a host material. Preferably, the light emitting layer may further include at least one dopant, and if necessary, may additionally include the organic electric device of the formula 1 of the present invention. A compound other than the photoluminescent compound is used as the second host material.

根據本發明之另一態樣，提供用於製備有機電致發光裝置的材料。材料包括第一主體材料及第二主體材料，其中第一主體材料包括本發明之有機電致發光化合物。第一主體材料與第二主體材料之間的重量比在1：99至99：1範圍內。 According to another aspect of the invention, a material for preparing an organic electroluminescent device is provided. The material includes a first host material and a second host material, wherein the first host material comprises the organic electroluminescent compound of the present invention. The weight ratio between the first body material and the second body material is in the range of 1:99 to 99:1.

第二主體材料可來自已知磷光主體材料中的任一者。較佳地，第二主體材料可選自由以下式3至6之磷光主體組成之群。 The second host material can be from any of the known phosphorescent host materials. Preferably, the second host material is selected from the group consisting of phosphorescent bodies of the following formulas 3 to 6.

其中A1及A2各獨立地表示經取代或未經取代之(C6-C30)芳基；較佳各獨立地表示經取代或未經取代之(C6-C18)芳基；更佳各獨立地表示經氰基、(C1-C6)烷基、(C6-C12)芳基或三(C6-C12)芳基矽烷基取代或未經取代之(C6-C18)芳基；及再更佳各獨立地表示苯基、聯苯、聯三苯、萘基、茀基、菲基、蒽基、茚基、聯伸三苯基、芘基、并四苯基、苝基、艸快基 或茀蒽基。 Wherein A 1 and A 2 each independently represent a substituted or unsubstituted (C6-C30) aryl group; preferably each independently represents a substituted or unsubstituted (C6-C18) aryl group; more preferably each independently (C6-C18) aryl substituted or unsubstituted with cyano, (C1-C6)alkyl, (C6-C12) aryl or tri(C6-C12)arylalkylalkyl; and more preferably Each independently represents phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, fluorenyl, —triphenyl, fluorenyl, tetraphenyl, fluorenyl, fluorenyl or hydrazine蒽基.

X1至X16各獨立地表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C6-C60)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之三(C1-C30)烷基矽烷基、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二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基或經取代或未經取代之單-或二-(C6-C30)芳基胺基；可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C30)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自氮、氧及硫之雜原子置換；較佳各獨立地表示氫、氰基、經取代或未經取代之(C6-C20)芳基、經取代或未經取代之(5至20員)雜芳基或經取代或未經取代之三(C6-C12)芳基矽烷基；更佳各獨立地表示氫、氰基、經氰基取代或未經取代之(C6-C20)芳基、未經取代之(5至20員)雜芳基或未經取代之三(C6-C12)芳基矽烷基。 X 1 to X 16 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted Or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30)alkyldecyl, substituted or unsubstituted tris(C6-C30)aryldecyl, substituted or Unsubstituted bis(C1-C30)alkyl(C6-C30)aryldecyl, substituted or unsubstituted (C1-C30)alkylbis(C6-C30)aryldecyl or substituted or Unsubstituted mono- or di-(C6-C30)arylamino group; may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C30), monocyclic or polycyclic, alicyclic ring Or an aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; preferably each independently represents hydrogen, cyano, substituted or unsubstituted (C6-C20) aryl, Substituted or unsubstituted (5 to 20 membered) heteroaryl or substituted or unsubstituted tris (C6-C 12) arylalkylalkyl; more preferably each independently represents hydrogen, cyano, cyano substituted or unsubstituted (C6-C20) aryl, unsubstituted (5 to 20 membered) heteroaryl or not Substituted tris(C6-C12) aryldecylalkyl.

L1表示經取代或未經取代之(C6-C30)伸芳基，較佳經取代或未經取代之(C6-C15)伸芳基，且更佳經氰基、(C1-C6)烷基或三(C6-C12)芳基矽烷基取代或未經取代之(C6-C15)伸芳基。 L 1 represents a substituted or unsubstituted (C6-C30) extended aryl group, preferably a substituted or unsubstituted (C6-C15) extended aryl group, and more preferably a cyano group, (C1-C6) alkane. A (C6-C12) arylalkyl group substituted or unsubstituted (C6-C15) extended aryl group.

此外，L1可由下式7至19中之任一者表示。 Further, L 1 may be represented by any one of the following formulas 7 to 19.

其中Xi至Xp各獨立地表示氫、氘、鹵素、氰基、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C6-C60)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之三(C1-C30)烷基矽烷基、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二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基或經取代或未經取代之單-或二-(C6-C30)芳基胺基；或可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C30)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自由氮、氧及硫組成之群的雜原子置換；及 表示鍵結位點。 Wherein Xi to Xp each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or Unsubstituted (C2-C30)alkynyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3 to 30 members) heteroaryl, substituted or unsubstituted tri(C1-C30)alkyldecyl, substituted or unsubstituted tris(C6-C30)aryldecyl, substituted or not Substituted bis(C1-C30)alkyl(C6-C30)aryldecyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)aryldecyl or substituted or not Substituted mono- or di-(C6-C30)arylamino group; or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C30), monocyclic or polycyclic, alicyclic ring Or an aromatic ring, the carbon atom of which may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; Indicates the bonding site.

特定言之，第二主體材料較佳包含以下： In particular, the second host material preferably comprises the following:

根據本發明之一個實施例，本發明之有機電致發光裝置包括陽極、陰極及至少一個安置於陽極與陰極之間的發光層，其中發光層包括主體材料及磷光摻雜劑材料；主體材料由兩種或兩種以上主體化合物組成；且兩種或兩種以上主體化合物中之第一主體化合物為由式1表示之化合物且第二主體化合物為由式3至6中的任一者表示之化合物。 According to an embodiment of the present invention, an organic electroluminescent device of the present invention comprises an anode, a cathode and at least one luminescent layer disposed between the anode and the cathode, wherein the luminescent layer comprises a host material and a phosphorescent dopant material; One or two or more kinds of host compounds; and the first host compound of the two or more host compounds is a compound represented by Formula 1, and the second host compound is represented by any one of Formulas 3 to 6. Compound.

發光層指示發射光之層，其可為單層；且亦可為由兩個或兩個以上層堆疊之多層。摻雜化合物之摻雜量以主體化合物及摻雜化合物之總量計較佳小於20重量%。 The luminescent layer indicates a layer that emits light, which may be a single layer; and may also be a plurality of layers stacked by two or more layers. The doping amount of the doping compound is preferably less than 20% by weight based on the total of the host compound and the dopant compound.

本發明之有機電致發光裝置中包括之摻雜劑較佳為至少一種磷光摻雜劑。用於本發明之有機電致發光裝置的磷光摻雜劑材料不受限制，但可較佳選自銥(Ir)、鋨(Os)、銅(Cu)或鉑(Pt)之金屬化錯合化合物，更佳選自銥(Ir)、鋨(Os)、銅(Cu)或鉑(Pt)之鄰位金屬化錯合化合物，且甚至更佳為鄰位金屬化銥錯合化合物。 The dopant included in the organic electroluminescent device of the present invention is preferably at least one phosphorescent dopant. The phosphorescent dopant material used in the organic electroluminescent device of the present invention is not limited, but may preferably be selected from metallization of Ir (Ir), O(Os), Copper (Cu) or Platinum (Pt). The compound, more preferably an ortho-metalated compound selected from the group consisting of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably an ortho-metallated ruthenium complex compound.

由下式101至103表示之化合物可用作本發明之有機電致發光裝置中將包括之摻雜劑。 The compound represented by the following formulas 101 to 103 can be used as a dopant which will be included in the organic electroluminescence device of the present invention.

其中L選自以下結構： Where L is selected from the following structures:

R100表示氫、經取代或未經取代之(C1-C30)烷基或經取代或未經取代之(C3-C30)環烷基；R101至R109及R111至R123各獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、氰基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基或經取代或未經取代之(C3-C30)環烷基；R106至R109可鍵聯至鄰近取代基形成經取代或未經取代之稠環，例如未經取代或經烷基取代之茀、未經取代或經烷基取代之二苯并噻吩或未經取代或經烷基取代之二苯并呋喃；R120至R123可鍵聯至鄰近取代基形成經取代或未經取代之稠環，例如未經取代或經烷基或芳基取代之喹啉；R124至R127各獨立地表示氫、氘、鹵素、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；R124至R127可鍵聯至鄰近取代基形成經取代或未經取代之稠環， 例如未經取代或經烷基取代之茀、未經取代或經烷基取代之二苯并噻吩或未經取代或經烷基取代之二苯并呋喃；R201至R211各獨立地表示氫、氘、鹵素、未經取代或經鹵素取代之(C1-C30)烷基、經取代或未經取代之(C3-C30)環烷基或經取代或未經取代之(C6-C30)芳基；R208至R211可鍵聯至鄰近取代基形成經取代或未經取代之稠環，例如未經取代或經烷基取代之茀、未經取代或經烷基取代之二苯并噻吩或未經取代或經烷基取代之二苯并呋喃；r及s各獨立地表示1至3之整數；當r或s為2或2以上之整數時，R100中之每一者可相同或不同；及e表示1至3之整數。 R 100 represents hydrogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C3-C30) cycloalkyl; R 101 to R 109 and R 111 to R 123 are each independently Represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, cyano, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6 -C30) aryl or substituted or unsubstituted (C3-C30)cycloalkyl; R 106 to R 109 may be bonded to adjacent substituents to form a substituted or unsubstituted fused ring, such as unsubstituted or Alkyl-substituted fluorene, unsubstituted or alkyl-substituted dibenzothiophene or unsubstituted or alkyl-substituted dibenzofuran; R 120 to R 123 may be bonded to adjacent substituents to form substituted Or an unsubstituted fused ring, such as an unsubstituted or substituted alkyl or aryl group; R 124 to R 127 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) An alkyl group or a substituted or unsubstituted (C6-C30) aryl group; R 124 to R 127 may be bonded to an adjacent substituent to form a substituted or unsubstituted fused ring, such as unsubstituted or alkyl Replace it Unsubstituted or alkyl-substituted dibenzothiophene or unsubstituted or alkyl-substituted dibenzofuran; R 201 to R 211 each independently represent hydrogen, deuterium, halogen, unsubstituted or halogenated Substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl or substituted or unsubstituted (C6-C30) aryl; R 208 to R 211 can be bonded to Adjacent substituents form a substituted or unsubstituted fused ring, such as unsubstituted or alkyl substituted fluorene, unsubstituted or alkyl substituted dibenzothiophene or unsubstituted or alkyl substituted Benzofuran; r and s each independently represent an integer from 1 to 3; when r or s is an integer of 2 or more, each of R 100 may be the same or different; and e represents an integer from 1 to 3. .

特定言之，磷光摻雜劑包含以下： In particular, phosphorescent dopants include the following:

本發明之有機電致發光裝置包括式1之有機電致發光化合物，且可進一步包括至少一種選自由芳基胺類化合物及苯乙烯基芳基胺類化合物組成之群的化合物。 The organic electroluminescent device of the present invention comprises the organic electroluminescent compound of Formula 1, and may further comprise at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds.

在本發明之有機電致發光裝置中，除式1化合物以外，有機層可進一步包括至少一種選自由以下組成之群的金屬：週期表之第1族金屬、第2族金屬、第4週期過渡金屬、第5週期過渡金屬、鑭系元素及d-過渡元素之有機金屬，或至少一種包括所述金屬之錯合化合物。有機層可進一步包括發光層及電荷產生層。 In the organic electroluminescent device of the present invention, in addition to the compound of the formula 1, the organic layer may further comprise at least one metal selected from the group consisting of: Group 1 metal of the periodic table, Group 2 metal, transition of the 4th cycle The metal, the fifth periodic transition metal, the organometallic of the lanthanide and the d-transition element, or at least one compound comprising the metal. The organic layer may further include a light emitting layer and a charge generating layer.

另外，本發明之有機電致發光裝置可藉由進一步包括至少一個發光層來發射白光，所述發光層除本發明之化 合物以外，包括此項技術中已知之藍色電致發光化合物、紅色電致發光化合物或綠色電致發光化合物。視需要，其可進一步包括橙光發射層或黃光發射層。 In addition, the organic electroluminescent device of the present invention can emit white light by further including at least one light emitting layer, which is in addition to the present invention. In addition to the compounds, blue electroluminescent compounds, red electroluminescent compounds or green electroluminescent compounds known in the art are included. It may further include an orange light emitting layer or a yellow light emitting layer as needed.

在本發明之有機電致發光裝置中，較佳地，至少一個層(在下文中「表層」)可置放在一個或兩個電極之內表面上，所述層選自硫屬化物層、金屬鹵化物層及金屬氧化層。特定言之，具有矽或鋁之硫屬化物(包含氧化物)層較佳置於電致發光中間層之陽極表面上，且金屬鹵化物層或金屬氧化物層較佳置於電致發光中間層之陰極表面上。此類表層為有機電致發光裝置提供操作穩定性。較佳地，所述硫屬化物包含SiOX(1X2)、AlOX(1X1.5)、SiON、SiAlON等；所述金屬鹵化物包含LiF、MgF2、CaF2、稀土金屬氟化物等；且所述金屬氧化物包含Cs2O、Li2O、MgO、SrO、BaO、CaO等。 In the organic electroluminescent device of the present invention, preferably, at least one layer (hereinafter "surface layer") may be placed on the inner surface of one or both electrodes selected from a chalcogenide layer and a metal. a halide layer and a metal oxide layer. In particular, a chalcogenide (including oxide) layer having ruthenium or aluminum is preferably disposed on the anode surface of the electroluminescent intermediate layer, and the metal halide layer or metal oxide layer is preferably placed in the middle of electroluminescence. On the cathode surface of the layer. Such skin layers provide operational stability to organic electroluminescent devices. Preferably, the chalcogenide comprises SiO X (1 X 2), AlO X (1 X 1.5), SiON, SiAlON, etc.; the metal halide comprises LiF, MgF 2 , CaF 2 , rare earth metal fluoride, etc.; and the metal oxide comprises Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO Wait.

在本發明之有機電致發光裝置中，電子傳輸化合物及還原性摻雜劑之混合區、或電洞傳輸化合物及氧化性摻雜劑之混合區可置放在一對電極之至少一個表面上。在此情況下，電子傳輸化合物還原成陰離子，且因此變得更容易自混合區注入及傳輸電子至電致發光介質。另外，電洞傳輸化合物氧化成陽離子，且因此變得更容易自混合區注入及傳輸電洞至電致發光介質。較佳地，氧化性摻雜劑包含各種路易斯酸(Lewis acid)及受體化合物；且還原性摻雜劑包含鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬以及其混合物。還原性摻雜劑層可用作電荷產生層以製備具有兩個或兩個以上發光層且發射白光之電致發光裝置。 In the organic electroluminescent device of the present invention, 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 may be placed on at least one surface of the pair of electrodes . In this case, the electron transporting compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixing zone to the electroluminescent medium. In addition, the hole transport compound oxidizes to a cation, and thus it becomes easier to inject and transport holes from the mixing zone to the electroluminescent medium. Preferably, the oxidizing dopant comprises various Lewis acids and acceptor compounds; and the reducing dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, a rare earth metal, and a mixture thereof. The reducing dopant layer can be used as a charge generating layer to prepare an electroluminescent device having two or more light emitting layers and emitting white light.

為了形成本發明之有機電致發光裝置的各層，可使用乾式成膜方法，諸如真空蒸發、濺射、電漿及離子電鍍方法；或濕式成膜方法，諸如旋塗、浸塗及流塗方法。 In order to form the layers of the organic electroluminescent device of the present invention, dry film forming methods such as vacuum evaporation, sputtering, plasma, and ion plating methods; or wet film forming methods such as spin coating, dip coating, and flow coating may be used. method.

當使用濕式成膜方法時，薄膜可藉由將形成各層之材料溶解或擴散至任何適合溶劑中來形成，所述溶劑諸如乙醇、氯仿、四氫呋喃、二噁烷等。溶劑可為形成各層之材料可溶解或擴散於其中且不存在成膜能力問題的任何溶劑。 When a wet film forming method is used, the film can be formed by dissolving or diffusing a material forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like. The solvent may be any solvent in which the material forming the layers is soluble or diffusible and there is no problem of film forming ability.

實例1：製備化合物A-1 Example 1: Preparation of Compound A -1

1)製備化合物1-11) Preparation of compound 1-1

在將化合物B-1(50g，267mmol)、雙(頻哪醇根基)二硼(88g，347mmol)、二氯化雙(三苯基膦)鈀(II)(Pd(PPh3)Cl2)(9g，13.35mmol)、KOAc(65g，667mmol)及1,4-二噁烷(1.3L)添加及溶解至燒瓶中之後，使混合物在130℃下反應。在完成反應之後，用乙酸乙酯萃取有機層。用硫酸鎂自獲得之有機層移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物1-1(38g，產率：61%)。 In the compound B-1 (50 g, 267 mmol), bis(pinacolyl)diboron (88 g, 347 mmol), bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh 3 )Cl 2 ) After (9 g, 13.35 mmol), KOAc (65 g, 667 mmol) and 1,4-dioxane (1.3 L) were added and dissolved in a flask, the mixture was allowed to react at 130 °C. After completion of the reaction, the organic layer was extracted with ethyl acetate. The remaining water was removed from the obtained organic layer with magnesium sulfate. Subsequently, the organic layer was dried. The remaining product was subjected to column chromatography to give Compound 1-1 (38 g, yield: 61%).

2)製備化合物1-22) Preparation of compound 1-2

在將化合物B-2(100g，423mmol)、(2-氯苯基)酸(73g，466mmol)、肆(三苯基膦)鈀(0)(Pd(PPh3)4)(24 g，21mmol)、Na2CO3(89g，846mmol)、水(423mL)及甲苯(1.6L)添加及溶解至燒瓶中之後，使混合物處於回流下120℃下4小時。在完成反應之後，用乙酸乙酯萃取有機層，且用硫酸鎂移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物1-2(74.6g，產率：66%)。 In the compound B-2 (100 g, 423 mmol), (2-chlorophenyl) Acid (73 g, 466 mmol), hydrazine (triphenylphosphine) palladium (0) (Pd(PPh 3 ) 4 ) (24 g, 21 mmol), Na 2 CO 3 (89 g, 846 mmol), water (423 mL) and toluene ( After 1.6 L) was added and dissolved in the flask, the mixture was brought to reflux at 120 ° C for 4 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried. The remaining product was subjected to column chromatography to give Compound 1-2 (74.6 g, yield: 66%).

3)製備化合物1-33) Preparation of compounds 1-3

在將化合物1-1(38g，162mmol)、化合物1-2(43g，162mmol)、肆(三苯基膦)鈀(0)(Pd(PPh3)4)(9.4g，8mmol)、2M K2CO3水溶液(202mL)、甲苯(810mL)及EtOH(202mL)添加及溶解至燒瓶中之後，使混合物處於回流下120℃下2小時。在完成反應之後，用乙酸乙酯萃取有機層，且用硫酸鎂移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物1-3(25g，產率：52%)。 Compound 1-1 (38 g, 162 mmol), compound 1-2 (43 g, 162 mmol), hydrazine (triphenylphosphine) palladium (0) (Pd(PPh 3 ) 4 ) (9.4 g, 8 mmol), 2M K After 2 CO 3 aqueous solution (202 mL), toluene (810 mL) and EtOH (202 mL) were added and dissolved in the flask, the mixture was refluxed at 120 ° C for 2 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried. The remaining product was subjected to column chromatography to give Compound 1-3 (25 g, yield: 52%).

4)製備化合物1-44) Preparation of compounds 1-4

在將化合物1-3(25g，85mmol)及二氯甲烷(DCM)(848mL)添加至燒瓶中之後，冷卻混合物至0℃。在添加三溴硼烷(BBr3)(12mL，127mmol)之後，使混合物反應13小時。在完成反應之後，用乙酸乙酯萃取有機層，且用硫酸鎂移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物1-4(24g，產率：100%)。 After compound 1-3 (25 g, 85 mmol) and dichloromethane (DCM) (848 mL) were added to the flask, the mixture was cooled to 0 °C. After the addition of tribromoborane (BBr 3 ) (12 mL, 127 mmol), the mixture was reacted for 13 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried. The remaining product was subjected to column chromatography to give Compound 1-4 (24 g, yield: 100%).

5)製備化合物1-55) Preparation of compounds 1-5

在將化合物1-4(24g，85mmol)、參(二苯亞甲基丙酮)二鈀(0)(Pd2(dba3)(4g，4.2mmol)、s-Phos(3.5g，8.5mmol)、NaOt-Bu(21g，214mmol)及鄰二甲苯(570mL)添加及溶解至燒瓶中之後，使混合物處於回流下160℃下14 小時。在完成反應之後，用乙酸乙酯萃取有機層，且用硫酸鎂移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物1-5(16.6g，產率：80%)。 In the compound 1-4 (24 g, 85 mmol), bis(dibenzylideneacetone) dipalladium (0) (Pd 2 (dba 3 ) (4 g, 4.2 mmol), s-Phos (3.5 g, 8.5 mmol) After NaOt-Bu (21 g, 214 mmol) and o-xylene (570 mL) were added and dissolved in the flask, the mixture was refluxed at 160 ° C for 14 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate and used The residual moisture was removed by magnesium sulfate. Subsequently, the organic layer was dried. The residue was subjected to column chromatography to give compound 1-5 (16.6 g, yield: 80%).

6)製備化合物1-66) Preparation of compounds 1-6

在將化合物1-5(25.6g，105mmol)溶解於THF(525mL)中之後，冷卻混合物至-78℃。在添加之後，添加2.5M正丁基鋰(54mL，136mmol)且攪拌混合物3小時。隨後，添加1,2-二溴乙烷(13.6mL，157.5mmol)，且使混合物反應。在完成反應之後，用二氯甲烷萃取有機層，且用硫酸鎂移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物1-6(27g，產率：80%)。 After dissolving compound 1-5 (25.6 g, 105 mmol) in THF (525 mL), the mixture was cooled to -78 °C. After the addition, 2.5 M n-butyllithium (54 mL, 136 mmol) was added and the mixture was stirred for 3 hr. Subsequently, 1,2-dibromoethane (13.6 mL, 157.5 mmol) was added, and the mixture was allowed to react. After completion of the reaction, the organic layer was extracted with dichloromethane, and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried. The remaining product was subjected to column chromatography to give Compound 1-6 (27 g, yield: 80%).

7)製備化合物1-77) Preparation of compounds 1-7

在將化合物1-6(27g，84mmol)、2-氯苯胺(13mL，125mmol)、乙酸鈀(II)(Pd(OAc)2)(754mg，3.36mmol)、三-第三丁基膦(P(t-Bu)3)(1.7ml，6.72mmol)、NaOtBu(20g，210mmol)及鄰二甲苯(840mL)添加至燒瓶中之後，使混合物處於回流下3小時。在完成反應之後，用乙酸乙酯萃取有機層，且用硫酸鎂移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物1-7(1.1g，產率：35%)。 Compound 1-6 (27 g, 84 mmol), 2-chloroaniline (13 mL, 125 mmol), palladium(II) acetate (Pd(OAc) 2 ) (754 mg, 3.36 mmol), tri-tert-butylphosphine (P) After (t-Bu) 3 ) (1.7 ml, 6.72 mmol), NaOtBu (20 g, 210 mmol) and o-xylene (840 mL) were added to the flask, the mixture was refluxed for 3 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried. The residual product was subjected to column chromatography to give compound 1-7 (1.1g, yield: 35%).

8)製備化合物1-88) Preparation of compounds 1-8

在將化合物1-7(10g，27mmol)、乙酸鈀(II)(Pd(OAc)2)(607mg，2.7mmol)、三環己基膦四氟硼酸鹽(PCy3HBF4)(2g，5.4mmol)、碳酸銫(18g，54mmol)及鄰二甲苯(270mL)添加至燒瓶中之後，使混合物處於回流下16小時。在完成反應之後，用乙酸乙酯萃取有機層，且用 硫酸鎂移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物1-8(7.9g，產率：88%)。 Compound 1-7 (10 g, 27 mmol), palladium(II) acetate (Pd(OAc) 2 ) (607 mg, 2.7 mmol), tricyclohexylphosphine tetrafluoroborate (PCy 3 HBF 4 ) (2 g, 5.4 mmol) After cesium carbonate (18 g, 54 mmol) and o-xylene (270 mL) were added to the flask, the mixture was refluxed for 16 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried. The remaining product was subjected to column chromatography to give Compound 1-8 (7.9 g, yield: 88%).

9)製備化合物A-19) Preparation of Compound A-1

在將化合物1-8(3g，9mmol)、化合物B-3(4.5g，12mmol)、乙酸鈀(II)(Pd(OAc)2)(101mg，0.45mmol)、s-Phos(369mg，0.9mmol)、NaOt-Bu(2.2g，22.5mmol)及鄰二甲苯(45mL)添加至燒瓶中之後，使混合物處於回流下2小時。在完成反應之後，用乙酸乙酯萃取有機層，且用硫酸鎂移除剩餘水分。隨後，乾燥有機層。使剩餘產物經受管柱層析，獲得化合物A-1(3.6g，產率：62%)。 Compound 1-8 (3 g, 9 mmol), Compound B-3 (4.5 g, 12 mmol), palladium(II) acetate (Pd(OAc) 2 ) (101 mg, 0.45 mmol), s-Phos (369 mg, 0.9 mmol) After adding NaOt-Bu (2.2 g, 22.5 mmol) and o-xylene (45 mL) to the flask, the mixture was refluxed for 2 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate, and the remaining water was removed with magnesium sulfate. Subsequently, the organic layer was dried. The remaining product was subjected to column chromatography to give Compound A-1 (3.6 g, yield: 62%).

化合物：A-1，白色固體，Mp 288℃，1H NMR(CDCl3,TMS)δ 6.01-6.02(dd,1H),7.02-7.05(t,1H),7.07-7.10(t,1H),7.34-7.36(t,1H),7.45-7.49(m,3H),7.51-7.58(m,4H),7.58-7.61(m,4H),7.62-7.65(m,2H),7.75-7.76(d,1H),7.95(m,2H),8.02-8.03(d,1H),8.14-8.16(d,1H),8.81-8.83(dd,4H),9.08(m,2H),13C NMR(CDCl3,TMS)δ 110.3,117.0,119.9,120.4,120.8,122.1,123.6,125.4,126.5,126.6,127.7,128.1,128.7,128.9,129.0,129.3,129.4,130.2,130.9,131.3,132.6,133.4,135.0,136.2,136.5,137.7,141.9,142.8,146.1,160.1,170.9,171.8 Compound: A-1, white solid, Mp 288 ° C, 1 H NMR (CDCl 3 , TMS) δ 6.01-6.02 (dd, 1H), 7.02-7.05 (t, 1H), 7.07-7.10 (t, 1H), 7.34-7.36(t,1H), 7.45-7.49(m,3H),7.51-7.58(m,4H),7.58-7.61(m,4H),7.62-7.65(m,2H),7.75-7.76(d , 1H), 7.95 (m, 2H), 8.02-8.03 (d, 1H), 8.14-8.16 (d, 1H), 8.81-8.83 (dd, 4H), 9.08 (m, 2H), 13 C NMR (CDCl) 3 , TMS) δ 110.3, 117.0, 119.9, 120.4, 120.8, 122.1, 123.6, 125.4, 126.5, 126.6, 127.7, 128.1, 128.7, 128.9, 129.0, 129.3, 129.4, 130.2, 130.9, 131.3, 132.6, 133.4, 135.0 , 136.2, 136.5, 137.7, 141.9, 142.8, 146.1, 160.1, 170.9, 171.8

[裝置實例1-1]藉由作為主體之本發明之第一主體化合物及第二主體化合物之共蒸發產生的OLED裝置[Device Example 1-1] OLED device produced by co-evaporation of the first host compound and the second host compound of the present invention as a host

如下藉由使用本發明之有機電致發光化合物產 生OLED裝置。使用於有機發光二極體(OLED)之玻璃基板上之透明電極氧化銦錫(ITO)薄膜(10Ω/□)(Samsung Corning)經受依序用三氯乙烯、丙酮、乙醇及蒸餾水的超音波洗滌，且隨後儲存於異丙醇中。接著，將ITO基板安裝於真空氣相沈積設備之基板固持器上。將1,4,5,8,9,12-六氮雜聯伸三苯-六甲腈(化合物HI-1)引入至所述真空氣相沈積設備之單元中，且接著將所述設備之腔室中的壓力控制為10-6托。此後，向所述單元施加電流以使上述引入之材料蒸發，由此在ITO基板上形成厚度為5nm之第一電洞注入層。隨後向所述真空氣相沈積設備之另一單元引入N,N'-雙(萘-1-基)-N,N'-雙(苯基)-聯苯胺(化合物HI-2)，且藉由向所述單元施加電流來蒸發，從而在第一電洞注入層上形成厚度為95nm之第二電洞注入層。隨後向所述真空氣相沈積設備之另一單元引入N-([1,1'-聯苯]-4-基)-9,9-二甲基-N-(4-(9-苯基-9H-咔唑-3-基)苯基)-9H-茀-2-胺(化合物HT-1)，且藉由向所述單元施加電流來蒸發，藉此在第二電洞注入層上形成厚度為20nm之電洞傳輸層。在形成電洞注入層及電洞傳輸層之後，如下在其上形成發光層。將作為主體材料之化合物A-1及H1-1分別引入真空氣相沈積設備之兩個單元中，且將作為摻雜化合物之化合物D-74引入另一單元中。兩種主體化合物隨後以1：1之相同比率蒸發，而摻雜劑以與主體化合物不同之比率蒸發，使得摻雜劑以按主體及摻雜劑之總量計12重量%之摻雜量沈積，以在電洞傳輸層上形成厚度為30nm之發光層。隨後向所述真空氣相沈積設備之另一單元引入2,4,6-參(9,9-二甲基-9H-茀-2-基)-1,3,5-三嗪(化合物ET-1)，且蒸發，藉此在發 光層上形成厚度為35nm之電子傳輸層。在沈積厚度為2nm之作為電子注入層之喹啉鋰(EI-1)後，隨後藉由另一真空氣相沈積設備在電子注入層上沈積厚度為80nm之Al陰極以製備OLED裝置。 An OLED device is produced by using the organic electroluminescent compound of the present invention as follows. Transparent electrode indium tin oxide (ITO) film (10 Ω / □) (Samsung Corning) used on a glass substrate of an organic light-emitting diode (OLED) was subjected to ultrasonic cleaning in sequence with trichloroethylene, acetone, ethanol and distilled water. And then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Introducing 1,4,5,8,9,12-hexazazatriphenyl-hexacarbonitrile (compound HI-1) into the unit of the vacuum vapor deposition apparatus, and then chamber of the apparatus The pressure in the control is 10 -6 Torr. Thereafter, a current was applied to the cell to evaporate the introduced material, thereby forming a first hole injecting layer having a thickness of 5 nm on the ITO substrate. Subsequently introducing N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine (compound HI-2) to another unit of the vacuum vapor deposition apparatus, and borrowing A second hole injection layer having a thickness of 95 nm is formed on the first hole injection layer by applying a current to the cell to evaporate. Subsequent introduction of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl) to another unit of the vacuum vapor deposition apparatus -9H-carbazol-3-yl)phenyl)-9H-indol-2-amine (compound HT-1), and is evaporated by applying a current to the unit, thereby being implanted on the second hole injection layer A hole transport layer having a thickness of 20 nm was formed. After the hole injection layer and the hole transport layer are formed, a light-emitting layer is formed thereon as follows. Compounds A-1 and H1-1 as host materials were respectively introduced into two units of a vacuum vapor deposition apparatus, and a compound D-74 as a doping compound was introduced into another unit. The two host compounds are then evaporated in the same ratio of 1:1, and the dopant is evaporated in a different ratio than the host compound such that the dopant is deposited in a doping amount of 12% by weight based on the total of the host and the dopant. To form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Subsequent introduction of 2,4,6-paran (9,9-dimethyl-9H-indol-2-yl)-1,3,5-triazine (compound ET) to another unit of the vacuum vapor deposition apparatus -1), and evaporated, whereby an electron transport layer having a thickness of 35 nm was formed on the light-emitting layer. After depositing lithium quinolate ( EI-1 ) as an electron injecting layer having a thickness of 2 nm, an Al cathode having a thickness of 80 nm was then deposited on the electron injecting layer by another vacuum vapor deposition apparatus to prepare an OLED device.

[裝置實例1-2]藉由蒸發作為唯一主體化合物之化合物A-1產生的OLED裝置[Device Example 1-2] OLED device produced by evaporating Compound A-1 as the sole host compound

除了使用化合物A-1作為發光層之唯一主體以外，以與裝置實例1-1中相同之方式產生OLED。 An OLED was produced in the same manner as in the device example 1-1, except that the compound A-1 was used as the sole host of the light-emitting layer.

[比較裝置實例1-1]藉由蒸發作為第一主體化合物之B-1產生的OLED裝置[Comparative Device Example 1-1] An OLED device produced by evaporating B-1 as a first host compound

除了使用化合物B-1作為發光層之主體以外，以與裝置實例1-1中相同之方式產生OLED。 An OLED was produced in the same manner as in the device example 1-1, except that the compound B-1 was used as the host of the light-emitting layer.

[比較裝置實例1-2]藉由蒸發作為唯一主體之B-1產生的OLED裝置[Comparative Device Example 1-2] OLED device produced by evaporating B-1 as the sole body

除了使用化合物B-1作為發光層之唯一主體以外，以與裝置實例1-2中相同之方式產生OLED。 An OLED was produced in the same manner as in the device example 1-2, except that the compound B-1 was used as the sole host of the light-emitting layer.

裝置實例1-1及1-2及比較實例1-1及1-2中產 生之有機電致發光裝置之在10mA/cm2電流密度下之驅動電壓及10,000尼特下之亮度自100%降低至95%所花費的時間(T95壽命)顯示在以下表1中。 The driving voltage at a current density of 10 mA/cm 2 and the luminance at 10,000 nits of the organic electroluminescent device produced in the device examples 1-1 and 1-2 and the comparative examples 1-1 and 1-2 were reduced from 100%. The time taken to 95% (T95 life) is shown in Table 1 below.

與習知有機電致發光裝置相比，本發明之有機電致發光裝置顯示藉由使用特定主體之極好壽命。 The organic electroluminescent device of the present invention exhibits an excellent lifetime by using a specific subject as compared with a conventional organic electroluminescent device.

Claims (9)

一種有機電致發光化合物，其由下式1表示： 其中X表示-O-、-S-或-NR9-；La表示單鍵、經取代或未經取代之(C6-C30)芳基或經取代或未經取代之(3至30員)雜芳基；Ma表示經取代或未經取代之(C6-C30)芳基或經取代或未經取代之(3至30員)雜芳基；A及B各獨立地表示經取代或未經取代之苯基或經取代或未經取代之萘基；R1至R9各獨立地表示氫、氘、鹵素、氰基、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(3至30員)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(C1-C30)烷氧基、經取代或未經取代之三(C1-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(C1-C30)烷基二(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單-或二-(C1-C30)烷基胺基、經取代或未經取代之單-或二-(C6-C30)芳基胺基或經取代或未經取代之 (C1-C30)烷基(C6-C30)芳基胺基；或可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C30)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自氮、氧及硫之雜原子置換；及所述雜芳基含有至少一個選自B、N、O、S、Si及P之雜原子。 An organic electroluminescent compound represented by the following formula 1: Wherein X represents -O-, -S- or -NR 9 -; La represents a single bond, a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3 to 30 member) Aryl; Ma represents substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3 to 30 membered) heteroaryl; A and B each independently represent substituted or unsubstituted a phenyl group or a substituted or unsubstituted naphthyl group; R 1 to R 9 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or Unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted Substituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkyldecane, substituted or unsubstituted bis(C1-C30)alkyl (C6-C30) aryl Alkyl, substituted or unsubstituted (C1-C30)alkyl di(C6-C30)aryldecyl, substituted or unsubstituted tris(C6-C30)aryldecyl, substituted or substituted Unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamine a substituted or unsubstituted (C1-C30)alkyl (C6-C30) arylamino group; or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C30), monocyclic ring. Or a polycyclic, alicyclic or aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; and the heteroaryl group containing at least one selected from the group consisting of B, N, O, S , Si and P heteroatoms. 如申請專利範圍第1項所述之有機電致發光化合物，其中所述式1化合物由下式2表示： 其中X、La、Ma及R1至R9如申請專利範圍第1項中所定義；R10至R15各獨立地表示氫、氘、鹵素、氰基、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(3至30員)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(C1-C30)烷氧基、經取代或未經取代之三(C1-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(C1-C30)烷基二(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單-或二-(C1-C30)烷基胺基、經取代或未經取代之單-或二-(C6-C30)芳基胺基或經取代或未經 取代之(C1-C30)烷基(C6-C30)芳基胺基；或可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C30)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自氮、氧及硫之雜原子置換；及所述雜芳基含有至少一個選自B、N、O、S、Si及P之雜原子。 The organic electroluminescent compound according to claim 1, wherein the compound of the formula 1 is represented by the following formula 2: Wherein X, La, Ma and R 1 to R 9 are as defined in claim 1; R 10 to R 15 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1 -C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted (C3-C30) Cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30)alkyldecyl, substituted or unsubstituted bis (C1-C30) Alkyl (C6-C30) arylalkyl, substituted or unsubstituted (C1-C30) alkyl di(C6-C30) arylalkyl, substituted or unsubstituted III (C6-C30 An arylalkylalkyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30) arylamino group or Substituted or unsubstituted (C1-C30)alkyl (C6-C30) arylamine; or may be bonded to adjacent substituents to form substituted or unsubstituted (C3-C30), monocyclic or poly a ring, an alicyclic ring or an aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; Heteroaryl group containing at least one heteroatom selected from B, N, O, S, Si and P of. 如申請專利範圍第1項所述之有機電致發光化合物，其中在式1中，La表示單鍵、經取代或未經取代之(C6-C20)芳基或經取代或未經取代之(3至20員)雜芳基，且Ma表示經取代或未經取代之(C6-C20)芳基或經取代或未經取代之(3至20員)雜芳基。 The organic electroluminescent compound according to claim 1, wherein in Formula 1, La represents a single bond, a substituted or unsubstituted (C6-C20) aryl group or a substituted or unsubstituted ( 3 to 20 members) heteroaryl, and Ma represents a substituted or unsubstituted (C6-C20) aryl group or a substituted or unsubstituted (3 to 20 membered) heteroaryl group. 如申請專利範圍第1項所述之有機電致發光化合物，其中在式1中，La表示單鍵、未經取代之(C6-C12)芳基或未經取代之三嗪基或吡啶基，且Ma表示經取代或未經取代之(C6-C12)芳基，或未經取代或經(C6-C20)芳基取代之苯基、聯三苯、三嗪基、吡啶基、喹啉基、喹唑啉基、嘧啶基或喹喏啉基。 The organic electroluminescent compound according to claim 1, wherein in Formula 1, La represents a single bond, an unsubstituted (C6-C12) aryl group or an unsubstituted triazinyl group or a pyridyl group, And Ma represents a substituted or unsubstituted (C6-C12) aryl group, or an unsubstituted or substituted (C6-C20) aryl group, phenyl, terphenyl, triazinyl, pyridyl, quinolyl , quinazolinyl, pyrimidinyl or quinoxalinyl. 如申請專利範圍第1項所述之有機電致發光化合物，其中在式1中，R1至R9各獨立地表示氫、氘、經取代或未經取代之(C1-C20)烷基、經取代或未經取代之(C6-C20)芳基、經取代或未經取代之(3至20員)雜芳基、經取代或未經取代之(C3-C20)環烷基、經取代或未經取代之(C1-C20)烷氧基、經取代或未經取代之三(C1-C20)烷基矽烷基、經取代或未經取代之二(C1-C20)烷基(C6-C20)芳基矽烷基、經取代或未經取代之(C1-C20)烷基二(C6-C20)芳基矽烷 基、經取代或未經取代之三(C6-C20)芳基矽烷基、經取代或未經取代之單-或二-(C1-C20)烷基胺基、經取代或未經取代之單-或二-(C6-C20)芳基胺基或經取代或未經取代之(C1-C20)烷基(C6-C20)芳基胺基；或可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C20)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自氮、氧及硫之雜原子置換；且所述雜芳基含有至少一個選自B、N、O、S、Si及P之雜原子。 The organic electroluminescent compound according to claim 1, wherein in Formula 1, R 1 to R 9 each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, Substituted or unsubstituted (C6-C20) aryl, substituted or unsubstituted (3 to 20 membered) heteroaryl, substituted or unsubstituted (C3-C20) cycloalkyl, substituted Or unsubstituted (C1-C20) alkoxy, substituted or unsubstituted tri(C1-C20)alkyldecane, substituted or unsubstituted bis(C1-C20)alkyl (C6- C20) aryl decyl, substituted or unsubstituted (C1-C20) alkyl di(C6-C20) arylalkyl, substituted or unsubstituted tri(C6-C20) arylalkyl, Substituted or unsubstituted mono- or di-(C1-C20)alkylamino, substituted or unsubstituted mono- or di-(C6-C20) arylamino group or substituted or unsubstituted a (C1-C20)alkyl (C6-C20) arylamine group; or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C20), monocyclic or polycyclic, alicyclic ring Or an aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; Group containing at least one hetero atom selected from B, N, O, S, Si and P of. 如申請專利範圍第1項所述之有機電致發光化合物，其中在式1中，所述經取代之(C1-C30)烷基、所述經取代之(C1-C30)烷氧基、所述經取代之(C3-C30)環烷基、所述經取代之(C6-C30)芳基、所述經取代之(3至30員)雜芳基及所述經取代之(C3-C30)單環或多環脂環族環或芳族環之所述取代基各獨立地為選自由以下組成之群的至少一者：氘、鹵素、氰基、羧基、硝基、羥基、(C1-C30)烷基、鹵基(C1-C30)烷基、(C2-C30)烯基、(C2-C30)炔基、(C1-C30)烷氧基、(C1-C30)烷硫基、(C3-C30)環烷基、(C3-C30)環烯基、(3至7員)雜環烷基、(C6-C30)芳氧基、(C6-C30)芳基硫基、經(C6-C30)芳基取代或未經取代之(5至30員)雜芳基、經(5至30員)雜芳基取代或未經取代之(C6-C30)芳基、三(C1-C30)烷基矽烷基、三(C6-C30)芳基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、(C1-C30)烷基二(C6-C30)芳基矽烷基、胺基、單-或二-(C1-C30)烷基胺基、單-或二-(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、(C1-C30)烷基羰基、(C1-C30)烷氧羰基、(C6-C30)芳 基羰基、二(C6-C30)芳基硼基、二(C1-C30)烷基硼基、(C1-C30)烷基(C6-C30)芳基硼基、(C6-C30)芳基(C1-C30)烷基及(C1-C30)烷基(C6-C30)芳基。 The organic electroluminescent compound according to claim 1, wherein in the formula 1, the substituted (C1-C30) alkyl group, the substituted (C1-C30) alkoxy group, Substituted (C3-C30)cycloalkyl, the substituted (C6-C30) aryl, the substituted (3 to 30 membered) heteroaryl, and the substituted (C3-C30) The substituents of the monocyclic or polycyclic alicyclic ring or the aromatic ring are each independently at least one selected from the group consisting of hydrazine, halogen, cyano, carboxyl, nitro, hydroxy, (C1) -C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3 to 7 membered)heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, C6-C30) aryl substituted or unsubstituted (5 to 30 membered) heteroaryl, substituted (5 to 30 membered) heteroaryl substituted or unsubstituted (C6-C30) aryl, tri(C1- C30) alkyl nonyl, tris(C6-C30)aryldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl, (C1-C30)alkyldi(C6-C30)aryl Base alkyl, amine, mono- or di-(C1-C30) alkylamine , mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl , (C6-C30) Fang Carbonyl group, di(C6-C30) aryl boron group, di(C1-C30)alkylboron group, (C1-C30)alkyl (C6-C30) aryl boron group, (C6-C30) aryl group ( C1-C30)alkyl and (C1-C30)alkyl (C6-C30) aryl. 如申請專利範圍第1項所述之有機電致發光化合物，其中所述由式1表示的化合物選自由以下組成之群： The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of: 一種有機電致發光裝置，其包括如申請專利範圍第1項所述之有機電致發光化合物。 An organic electroluminescence device comprising the organic electroluminescent compound according to claim 1 of the patent application. 一種有機電致發光裝置，其包括陽極、陰極及至少一個安置於所述陽極與陰極之間的發光層，其中所述發光層包括主體材料及磷光摻雜劑材料；所述主體材料由兩種或兩種以上主體化合物組成；且所述兩種或兩種以上主體化合物中之第一主體化合物為由如申請專利範圍第1項所述之式1表示之化合物且第二主體化合物為由式3至6中的任一者表示之化合物， 其中A1及A2各獨立地表示經取代或未經取代之(C6-C30)芳基；X1至X16各獨立地表示氫、氘、鹵素、氰基、經取代或未 經取代之(C1-C30)烷基、經取代或未經取代之(C2-C30)烯基、經取代或未經取代之(C2-C30)炔基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C6-C60)芳基、經取代或未經取代之(3至30員)雜芳基、經取代或未經取代之三(C1-C30)烷基矽烷基、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二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之(C1-C30)烷基二(C6-C30)芳基矽烷基或經取代或未經取代之單-或二-(C6-C30)芳基胺基；或可鍵聯至鄰近取代基形成經取代或未經取代之(C3-C30)、單環或多環、脂環族環或芳族環，其碳原子可經至少一個選自氮、氧及硫之雜原子置換；及L1表示經取代或未經取代之(C6-C30)伸芳基。 An organic electroluminescent device comprising an anode, a cathode and at least one luminescent layer disposed between the anode and the cathode, wherein the luminescent layer comprises a host material and a phosphorescent dopant material; Or a compound of two or more kinds of host compounds; and the first host compound of the two or more host compounds is a compound represented by Formula 1 as described in claim 1 and the second host compound is a formula a compound represented by any one of 3 to 6, Wherein A 1 and A 2 each independently represent a substituted or unsubstituted (C6-C30) aryl group; and X 1 to X 16 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted. (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C2-C30)alkynyl, substituted or unsubstituted (C3-C30) Cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted (3 to 30 membered) heteroaryl, substituted or unsubstituted tri(C1-C30) alkane Alkyl, substituted or unsubstituted tri(C6-C30)aryldecyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)aryldecyl, substituted or substituted Unsubstituted (C1-C30)alkyldi(C6-C30)aryldecylalkyl or substituted or unsubstituted mono- or di-(C6-C30)arylamine; or may be bonded to adjacent a substituent forming a substituted or unsubstituted (C3-C30), monocyclic or polycyclic, alicyclic or aromatic ring, the carbon atom of which may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; And L 1 represents a substituted or unsubstituted (C6-C30) extended aryl group.
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