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TW201307335A - Novel organic electroluminescence compounds and organic electroluminescence device using the same - Google Patents

Novel organic electroluminescence compounds and organic electroluminescence device using the same Download PDF

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TW201307335A
TW201307335A TW101126210A TW101126210A TW201307335A TW 201307335 A TW201307335 A TW 201307335A TW 101126210 A TW101126210 A TW 101126210A TW 101126210 A TW101126210 A TW 101126210A TW 201307335 A TW201307335 A TW 201307335A
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金侈植
金希淑
李孝姃
金慧美
文斗鉉
黃守振
李仙優
梁綬晉
李琇炫
李暻周
慎孝壬
朴景秦
趙英俊
權赫柱
金奉玉
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羅門哈斯電子材料韓國公司
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Abstract

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device containing the same. The compounds according to the present invention have high luminous efficiency and long operation lifetime. Therefore, they can produce an organic electroluminescent device having an improved power consumption.

Description

新穎有機電場發光化合物及使用該化合物之有機電場發光裝置 Novel organic electroluminescent compound and organic electric field illuminating device using the same

本發明係有關於新穎有機電場發光化合物及使用該化合物之有機電場發光裝置。 The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices using the same.

電場發光(electroluminescent，EL)裝置係自發光裝置，其具有提供寬廣視角、較高的對比以及快速的反應速率之優於其他類型顯示器裝置之優點。伊斯門-柯達(Eastman Kodak)首先研發出藉由使用小分子為芳香族二胺和鋁錯合物，作為形成電場發光層之材料之有機EL裝置[Appl.Phys.Lett.51,913,1987]。 An electroluminescent (EL) device is a self-illuminating device that has the advantage of providing a wide viewing angle, a higher contrast, and a faster reaction rate than other types of display devices. Eastman Kodak first developed an organic EL device using a small molecule as an aromatic diamine and an aluminum complex as a material for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987] .

決定有機EL裝置之發光效率的最重要因素係發光材料。至今，螢光材料已廣泛地用作為發光材料。然而，從電場發光機制的觀點來看，開發磷光材料是理論上提高四倍發光效率之最好方法之一。銥(III)錯合物係已廣為人知之磷光材料，其包含雙(2-(2’-苯并噻吩基)-吡啶-N,C3’)銥(乙醯丙酮)[(acac)Ir(btp)2]、參(2-苯基吡啶)銥[Ir(ppy)3]以及雙(4,6-二氟苯基吡啶-N,C2)甲吡啶銥(Firpic)，係分別作為紅光、綠光以及藍光材料。 The most important factor determining the luminous efficiency of an organic EL device is a luminescent material. Fluorescent materials have been widely used as luminescent materials to date. However, from the standpoint of the electric field luminescence mechanism, the development of phosphorescent materials is one of the best ways to theoretically increase the luminous efficiency by four times. A ruthenium (III) complex is a well-known phosphorescent material comprising bis(2-(2'-benzothienyl)-pyridine-N,C3') oxime (acetamidine) [(acac)Ir(btp) 2 ], ginseng (2-phenylpyridinium) oxime [Ir(ppy) 3 ] and bis(4,6-difluorophenylpyridine-N,C2)pyridinium (Firpic), respectively, as red light, Green light and blue light materials.

為了改善色純度、發光效率以及安定性，發光材料可以使用藉由將摻雜劑(dopant)與主體(host)材料混合而製備者。在該主體材料/摻雜劑系統中，由於該主體材料在EL裝置之效率與效能上具有相當大的影響，因而其之選擇格外重要。4,4’-N,N’-二咔唑-聯苯(CBP)係最廣為人知之 用於磷光物質之主體材料。再者，日本先鋒公司(Pioneer)等發展了高效能之有機EL裝置，該有機EL裝置使用浴銅靈(bathocuproine，BCP)作為主體材料，以及雙(2-甲基-8-羥基喹啉)(4-苯基酚)鋁(III)(BAlq)作為電洞阻擋層之材料。 In order to improve color purity, luminous efficiency, and stability, a luminescent material can be prepared by mixing a dopant with a host material. In the host material/dopant system, since the host material has a considerable influence on the efficiency and performance of the EL device, its selection is particularly important. 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known. A host material for a phosphorescent substance. Furthermore, Pioneer et al. developed a high-performance organic EL device using bathocuproine (BCP) as a host material and bis(2-methyl-8-hydroxyquinoline). (4-Phenylphenol) Aluminum (III) (BAlq) is used as a material for the hole barrier layer.

儘管這些磷光主體材料提供良好的發光特性，其仍具有下列缺點：(1)因為其有低玻璃轉化溫度以及熱安定性差，在真空高溫沉積製程期間可能會發生降解。(2)該有機EL裝置之功率效率係由下列公式所定義：[(Π/電壓)×電流效率]，且該功率效率係與電壓呈反比，因此需要高功率效率以減少功率消耗。雖然包括磷光材料之有機EL裝置相較於包括螢光材料者提供較高之電流效率(燭光/安培，cd/A)，該有機EL裝置具有明顯較高的驅動電壓。因此，使用傳統磷光材料之EL裝置就功率效率(流明/瓦，lm/W)來說並無優勢。(3)再者，該有機EL裝置之操作壽命短，且仍需改善發光效率。 Although these phosphorescent host materials provide good luminescent properties, they still have the following disadvantages: (1) Degradation may occur during the vacuum high temperature deposition process because of its low glass transition temperature and poor thermal stability. (2) The power efficiency of the organic EL device is defined by the following formula: [(Π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage, so high power efficiency is required to reduce power consumption. Although an organic EL device including a phosphorescent material provides higher current efficiency (candle/amperage, cd/A) than a person including a fluorescent material, the organic EL device has a significantly higher driving voltage. Therefore, an EL device using a conventional phosphorescent material has no advantage in terms of power efficiency (lumens/watt, lm/W). (3) Furthermore, the organic EL device has a short operational life and still needs to improve luminous efficiency.

韓國專利第0948700號揭露作為用於有機EL裝置之化合物之芳基咔唑化合物，其經包括氮原子之雜芳基取代之。然而，其未揭露在咔唑之第3位置經雜環烷基或與芳香環稠合之環烷基取代，且其直接或間接連接至經取代或未經取代之雜芳基之咔唑化合物。 Korean Patent No. 0948700 discloses an aryl carbazole compound as a compound for an organic EL device, which is substituted with a heteroaryl group including a nitrogen atom. However, it does not disclose a carbazole compound which is substituted at the 3rd position of the carbazole by a heterocycloalkyl group or a cycloalkyl group fused to an aromatic ring, and which is directly or indirectly bonded to a substituted or unsubstituted heteroaryl group. .

本發明之目的係提供一種有機電場發光化合物，其賦 予裝置高發光效率以及長操作壽命，以及具有適宜色座標；以及一種使用該化合物作為發光材料之有機電場發光裝置，其具有高效率以及長操作壽命。 The object of the present invention is to provide an organic electric field luminescent compound, which The device has high luminous efficiency and long operating life, and has suitable color coordinates; and an organic electric field illuminating device using the compound as a luminescent material, which has high efficiency and long operating life.

本發明之發明人發現上揭目的可以藉由下列式(1)表示之化合物達成： The inventors of the present invention have found that the above object can be achieved by the compound represented by the following formula (1):

其中，L1及L2各獨立表示單鍵、經取代或未經取代之3至30員伸雜芳基、經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之(C6-C30)伸環烷基；X1及X2各獨立表示CR’或N；Y表示-O-、-S-、-CR5R6-或-NR7-；Ar1、Ar2及R’各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、或經取代或未經取代之3至30員雜芳基；R1至R4各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之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5至7員雜環烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰基、硝基、或羥基；或其鍵結至相鄰之一個或多個取代基以形成單環或多環之(C5-C30)脂環或芳香環，且該環上之一個或多個碳原子可經至少一個選自氮、氧及硫之雜原子置換；R5至R7及R11至R17各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3至30員雜芳基、經取代或未經取代之5至7員雜環烷基、或經取代或未經取代之(C3-C30)環烷基；或其鍵結至相鄰之一個或多個取代基以形成單環或多環之(C5-C30)脂環或芳香環，且該環上之一個或多個碳原子可經至少一個選自氮、氧及硫之雜原子置換；a及c各獨立表示1至4之整數；當a或c係2或更多之整數時，每一個R1或每一個R3係相同或相異；b及d各獨立表示1至3之整數；當b或d係2或更多之整數時，每一個R2或每一個R4係相同或相異；以及該伸雜芳基、該雜環烷基及該雜芳基含有至少一個選自B、N、O、S、P(=O)、Si及P之雜原子。 Wherein, L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted 3 to 30 membered heteroaryl group, a substituted or unsubstituted (C6-C30) extended aryl group, or a substituted or unsubstituted group. Substituted (C6-C30)cycloalkylene; X 1 and X 2 each independently represent CR' or N; Y represents -O-, -S-, -CR 5 R 6 - or -NR 7 -; Ar 1 And Ar 2 and R′ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or not Substituted 3 to 30 membered heteroaryl; R 1 to R 4 each independently represent hydrogen, deuterium, halogen, 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 5 to 7 membered heterocycloalkane (C6-C30) aryl (C1-C30) alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitrate Or a hydroxyl group; or a bond to one or more adjacent substituents to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and on the ring One or more carbon atoms may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; R 5 to R 7 and R 11 to R 17 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted. (C1-C30)alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted 5 to 7 member a cycloalkyl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group; or a bond to one or more adjacent substituents to form a monocyclic or polycyclic (C5-C30) alicyclic ring Or an aromatic ring, and one or more carbon atoms of the ring may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; a and c each independently represent an integer from 1 to 4; when a or c is 2 or In more integers, each R 1 or each R 3 is the same or different; b and d each independently represent an integer from 1 to 3; when b or d is an integer of 2 or more, each R 2 Or each R 4 is the same or different; and the heteroaryl, the heterocycloalkyl and the heteroaryl contain at least one member selected from the group consisting of B, N, O, S, P(=O), Si, and P Hetero atom.

本發明之有機電場發光化合物可製造具有高發光效率及長操作壽命之有機電場發光裝置。 The organic electroluminescent compound of the present invention can produce an organic electric field light-emitting device having high luminous efficiency and long operational life.

此外，由於本發明之化合物具有高電子傳輸效率，當 製造裝置時可防止結晶。此外，該化合物具有良好的成層性及改善該裝置之電流特徵。因此，其可製造具有降低之驅動電壓及提升之功率效率的有機電場發光裝置。 In addition, since the compound of the present invention has high electron transport efficiency, when Crystallization is prevented when the device is manufactured. In addition, the compound has good layering properties and improves the current characteristics of the device. Therefore, it is possible to manufacture an organic electric field light-emitting device having a reduced driving voltage and improved power efficiency.

後文中將詳細描述本發明。然而，下文描述係意於解釋本發明，且不意欲以任何方式侷限本發明之範疇。 The invention will be described in detail hereinafter. 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.

本發明係關於上揭式(1)表示之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。 The present invention relates to an organic electroluminescent compound represented by the above formula (1), and an organic electric field light-emitting device comprising the same.

在此「(C1-C30)(伸)烷基」意指具有1至30個碳原子之直鏈或分支鏈(伸)烷基，其中，該碳原子之數量係較佳為1至20，更佳為1至10，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」意指具有2至30個碳原子之直鏈或分支鏈烯基，其中，該碳原子之數量係較佳為2至20，更佳為2至10，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」係具有2至30個碳原子之直鏈或分支鏈炔基，其中，該碳原子之數量係較佳為2至20，更佳為2至10，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；「(C3-C30)環烷基」係具有3至30個碳原子之單或多環烴，其中，該碳原子之數量係較佳為3至20，更佳為3至7，且包含環丙基、環丁基、環戊基、環己基等；「(C6-C30)伸環烷基」係藉由自環烷基上移除一個氫而形成者，其中該環烷基具有6至30個，較佳為6至20個， 更佳為6至12個碳原子；「3至7員雜環烷基」係具有至少一個選自B、N、O、S、P(=O)、Si及P之雜原子(較佳為O、S及N)以及3至7環主鏈原子之環烷基，且包含四氫呋喃、吡咯啶、四氫噻吩(thiolan)、四氫哌喃等；「(C6-C30)(伸)芳基」係衍生自具有6至30個碳原子之芳香烴類之單環或稠合環，其中，該碳原子數較佳為6至20、更佳為6至15，且包含苯基、聯苯基、聯三苯基、萘基、茀基、菲基、蒽基、茚基、聯伸三苯基(triphenylenyl)、芘基、并四苯基(tetracenyl)、苝基、蒯基(chrysenyl)、稠四苯基(naphthacenyl)、丙二烯合茀基(fluoranthenyl)等；「3至30員(伸)雜芳基」係具有至少一個(較佳為1至4個)雜原子以及3至30個環主鏈原子之芳基，其中該雜原子係選自B、N、O、S、P(=O)、Si以及P所組成之群組；係單環或與至少一個苯環縮合之稠合環；具有較佳為5至20個，更佳為5至15個環主鏈原子；可為部份飽合；可為藉由將至少一個雜芳基或芳基透過一個或多個單鍵鍵結至雜芳基而形成者；且包含單環類型雜芳基，包含呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、異噻唑基、異唑基、唑基、二唑基、三基、四基、三唑基、四唑基、呋吖基、吡啶基、吡基、嘧啶基、嗒基等，以及稠合環類型雜芳基，包含苯并呋喃基、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、苯并異唑基、苯并唑基、異吲哚基、吲哚基、吲唑基、苯并噻二唑基、 喹啉基、異喹啉基、噌啉基、喹唑啉基、喹啉基、咔唑基、啡基、啡啶基、苯并二呃基(benzodioxolyl)等。此外，「鹵素」包含F、Cl、Br及I。 Here, "(C1-C30)alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms, wherein the number of the carbon atoms is preferably from 1 to 20. More preferably 1 to 10, and it contains methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, etc.; "(C2-C30)alkenyl" means having 2 a linear or branched alkenyl group of up to 30 carbon atoms, wherein the number of carbon atoms is preferably from 2 to 20, more preferably from 2 to 10, and includes a vinyl group, a 1-propenyl group, and a 2-propenyl group. , 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.; "(C2-C30)alkynyl" has a straightness of 2 to 30 carbon atoms a chain or branched alkynyl group, wherein the number of carbon atoms is preferably from 2 to 20, more preferably from 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butyne , 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.; "(C3-C30)cycloalkyl" is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms Wherein the number of the carbon atoms is preferably from 3 to 20, more preferably from 3 to 7, and comprises a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc.; "(C6-C30) stretching a cycloalkyl group is formed by removing a hydrogen from a cycloalkyl group, wherein the cycloalkyl group has 6 to 30, preferably 6 to 20, more preferably 6 to 12 carbon atoms; The 3- to 7-membered heterocycloalkyl group has at least one hetero atom selected from B, N, O, S, P(=O), Si, and P (preferably O, S, and N) and a 3 to 7 ring. a cycloalkyl group of a main chain atom, and comprising tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.; "(C6-C30) (extended) aryl" is derived from having 6 to 30 carbon atoms a monocyclic or fused ring of an aromatic hydrocarbon, wherein the number of carbon atoms is preferably from 6 to 20, more preferably from 6 to 15, and comprises a phenyl group, a biphenyl group, a triphenylene group, a naphthyl group, and a fluorene group. , phenanthryl, fluorenyl, fluorenyl, triphenylenyl, fluorenyl, tetracenyl, fluorenyl, chrysenyl, naphthacenyl, propadiene Fluoranthenyl or the like; "3 to 30 member(extended)heteroaryl" is an aryl group having at least one (preferably 1 to 4) hetero atom and 3 to 30 ring main chain atoms, wherein The hetero atom is selected from the group consisting of B, N, O, S, P(=O), Si, and P. a single ring or a fused ring condensed with at least one benzene ring; preferably having 5 to 20, more preferably 5 to 15 ring backbone atoms; may be partially saturated; a heteroaryl or aryl group formed by one or more single bonds bonded to a heteroaryl group; and comprising a monocyclic type heteroaryl group, including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, Thiazolyl, thiadiazolyl, isothiazolyl, iso Azolyl, Azolyl, Diazolyl, three Base, four Base, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl Base, pyrimidinyl, oxime Base, and fused ring type heteroaryl, including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl Benzoisothiazolyl, benzopyrene Azolyl, benzo Azyl, isodecyl, decyl, oxazolyl, benzothiadiazolyl, quinolinyl, isoquinolyl, porphyrinyl, quinazolinyl, quin Orolinyl, carbazolyl, brown Peptidyl, benzodiyl Benzodioxolyl and the like. Further, "halogen" includes F, Cl, Br, and I.

本說明書中，在「經取代或未經取代」的表達中的「經取代」意為在特定官能基的氫原子經其他原子或基團(亦即，取代基)置換。在L1、L2、R’、Ar1、Ar2、R1至R4、R5至R7及R11至R17基團中之經取代之烷基、經取代之(伸)芳基、經取代之(伸)雜芳基、經取代之(伸)環烷基、經取代之雜環烷基、及經取代之芳烷基之取代基係各獨立為選自下列所組成群組之至少一者：氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C6-C30)芳基取代或未經取代之3至30員雜芳基、(C3-C30)環烷基、5至7員雜環烷基、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、(C2-C30)烯基、(C2-C30)炔基、氰基、N-咔唑基、二(C1-C30)烷基胺基、二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基；以及羥基。 In the present specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom of a specific functional group is substituted with another atom or a group (that is, a substituent). a substituted alkyl group in the group of L 1 , L 2 , R′, Ar 1 , Ar 2 , R 1 to R 4 , R 5 to R 7 and R 11 to R 17 , substituted (extended) The substituents of the substituted (extended) heteroaryl group, the substituted (extended) cycloalkyl group, the substituted heterocycloalkyl group, and the substituted aralkyl group are each independently selected from the group consisting of the following At least one of the group: anthracene, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, substituted by (C6-C30) aryl or unsubstituted 3 to 30-membered heteroaryl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, tri(C1-C30)alkyldecyl, tris(C6-C30)aryldecyl,di(C1- C30) alkyl (C6-C30) aryldecyl, (C1-C30)alkylbis(C6-C30)aryldecyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano , N-carbazolyl, di(C1-C30)alkylamino, di(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, di(C6- C30) aryl boron carbonyl, di(C1-C30)alkyl boroncarbonyl, (C1-C30)alkyl (C6-C30) aryl boroncarbonyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carboxyl, nitro; and hydroxy.

在上揭式(1)中，L1及L2各獨立表示單鍵、3至30員伸雜芳基、或(C6-C30)伸芳基；X1及X2各獨立表示CR’或N；Y表示-O-、-S-、-CR5R6-或-NR7-；Ar1、Ar2及R’各獨立表示氫、(C1-C30)烷基、(C6-C30)芳基、或3至30員雜芳基； R1至R4各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、3至30員雜芳基、-NR11R12、或-SiR13R14R15；或R3鍵結至相鄰之一個或多個取代基以形成單環或多環之(C5-C30)脂環或芳香環，且該環上之一個或多個碳原子可經至少一個選自氮、氧及硫之雜原子置換；R5至R7及R11至R17各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、或3至30員雜芳基；以及在L1及L2中之伸芳基及伸雜芳基及在Ar1、Ar2、R’、R1至R4、R5至R7及R11至R17中之烷基、芳基、及雜芳基各獨立可經選自下列所組成群組之至少一者取代：氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C6-C30)芳基取代或未經取代之3至30員雜芳基、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、N-咔唑基、二(C1-C30)烷基胺基、二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基；以及(C1-C30)烷基(C6-C30)芳基。 In the above formula (1), L 1 and L 2 each independently represent a single bond, a 3 to 30 membered heteroaryl group, or a (C6-C30) extended aryl group; and X 1 and X 2 each independently represent CR' or N; Y represents -O-, -S-, -CR 5 R 6 - or -NR 7 -; Ar 1 , Ar 2 and R' each independently represent hydrogen, (C1-C30)alkyl, (C6-C30) Aryl, or 3 to 30 membered heteroaryl; R 1 to R 4 each independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30)aryl, 3 to 30 membered heteroaryl, -NR 11 R 12 , or -SiR 13 R 14 R 15 ; or R 3 bonded to one or more adjacent substituents to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and One or more carbon atoms on the ring may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; R 5 to R 7 and R 11 to R 17 each independently represent hydrogen, deuterium, halogen, (C1-C30) An alkyl group, a (C6-C30) aryl group, or a 3 to 30 membered heteroaryl group; and an extended aryl group and a heteroaryl group in L 1 and L 2 and in Ar 1 , Ar 2 , R', R The alkyl group, the aryl group, and the heteroaryl group in each of 1 to R 4 , R 5 to R 7 and R 11 to R 17 may be independently substituted with at least one selected from the group consisting of hydrazine, halogen, and Halogen substituted or unsubstituted (C1-C 30) alkyl, (C6-C30) aryl, 3 to 30 membered heteroaryl substituted by (C6-C30) aryl, tri(C1-C30)alkyldecane, tris(C6- C30) aryl decyl, di(C1-C30)alkyl(C6-C30)aryldecyl, (C1-C30)alkylbis(C6-C30)aryldecyl, N-carbazolyl, (C1-C30)alkylamino, bis(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamine; and (C1-C30)alkyl (C6-C30) )Aryl.

在上揭式(1)中，較佳L1及L2各獨立表示單鍵、3至20員伸雜芳基、或(C6-C20)伸芳基，其中，該伸芳基可進一步經(C1-C10)烷基或(C6-C20)芳基取代。X1及X2各獨立表示CR’或N，其中，R’係較佳為(C6-C20)芳基，其中，該芳基可進一步經(C6-C20)芳基取代。Y表示-O-、-S-、-CR5R6-或-NR7-，其中，R5及R6較佳各獨立為(C1-C10)烷基、及R7係較佳為(C6-C20)芳基。Ar1及Ar2各獨立表示氫、或(C6-C20)芳基，其中，該芳基可進一步經氘、鹵素、(C1-C10) 烷基、(C6-C20)芳基、經(C6-C20)芳基取代或未經取代之3至20員雜芳基、三(C1-C10)烷基矽烷基、三(C6-C20)芳基矽烷基、二(C1-C10)烷基(C6-C20)芳基矽烷基、(C1-C10)烷基二(C6-C20)芳基矽烷基、或二(C6-C30)芳基胺基取代。R1至R4各獨立表示氫、鹵素、(C6-C20)芳基、-NR11R12、或-SiR13R14R15；或R3鍵結至相鄰之一個或多個取代基以形成單環或多環之(C5-C30)脂環或芳香環，且該環上之一個或多個碳原子可經至少一個選自氮、氧及硫之雜原子置換。R11至R17各獨立較佳為(C6-C20)芳基。 In the above formula (1), preferred L 1 and L 2 each independently represent a single bond, a 3 to 20 member heteroaryl group, or a (C6-C20) extended aryl group, wherein the extended aryl group may further (C1-C10)alkyl or (C6-C20)aryl substituted. X 1 and X 2 each independently represent CR' or N, wherein R' is preferably a (C6-C20) aryl group, wherein the aryl group may be further substituted with a (C6-C20) aryl group. Y represents -O-, -S-, -CR 5 R 6 - or -NR 7 -, wherein R 5 and R 6 are each independently (C1-C10)alkyl, and R 7 is preferably ( C6-C20) aryl. Ar 1 and Ar 2 each independently represent hydrogen or a (C6-C20) aryl group, wherein the aryl group may further be fluorene, halogen, (C1-C10) alkyl, (C6-C20) aryl, via (C6 -C20) aryl substituted or unsubstituted 3 to 20 membered heteroaryl, tri(C1-C10)alkyldecyl, tris(C6-C20)aryldecyl, di(C1-C10)alkyl ( C6-C20) aryldecyl, (C1-C10)alkylbis(C6-C20)aryldecyl, or di(C6-C30)arylamino substituted. R 1 to R 4 each independently represent hydrogen, halogen, (C6-C20) aryl, -NR 11 R 12 , or -SiR 13 R 14 R 15 ; or R 3 is bonded to one or more adjacent substituents. To form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and one or more carbon atoms of the ring may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur. R 11 to R 17 are each independently preferably a (C6-C20) aryl group.

更具體而言，L1及L2各獨立表示單鍵、伸苯基、伸聯苯基、伸聯三苯基、伸茚基、伸茀基、伸聯伸三苯基、伸芘基、伸苝基、伸蒯基(chrysenylene)、伸稠四苯基、伸丙二烯合茀基、伸噻吩基、伸吡咯基、伸吡唑基、伸噻唑基、伸唑基、伸二唑基、伸三基、伸四基、伸三唑基、伸呋吖基、伸吡啶基、伸苯并呋喃基、伸苯并噻吩基、伸吲哚基、伸苯并咪唑基、伸苯并噻唑基、伸苯并異噻唑基、伸苯并異唑基、伸苯并唑基、伸苯并噻二唑基、伸二苯并呋喃基、或伸二苯并噻吩基；Ar1、Ar2及R’各獨立表示氫、甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、異戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二基、十六基、三氟基甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、聯苯基、茀基、丙二烯合茀基(fluoranthcnyl)、聯三苯基、芘基、蒯基、稠四苯基(naphthacenyl)、苝基、 吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、喹啉基、三基、苯并呋喃基、二苯并呋喃基、苯并噻吩基、二苯并噻吩基、吡唑基、吲哚基、咔唑基、噻唑基、唑基、苯并噻唑基、苯并唑基、啡啉基、喹啉基、或N-咔唑基；R1至R4各獨立表示氫、氘、氯基、氟基、甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、異戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二基、十六基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、萘基、蒽基(anthryl)、聯苯基、茀基、丙二烯合茀基、聯伸三苯基、芘基、蒯基、稠四苯基、苝基、吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、茚基、吡基、嘧啶基、嗒基、喹啉基、三基、苯并呋喃基、二苯并呋喃基、苯并噻吩基、二苯并噻吩基、吡唑基、吲哚基、咔唑基、噻唑基、唑基、苯并噻唑基、苯并唑基、啡啉基、N-咔唑基、二甲基胺基、二乙基胺基、甲基苯基胺基、二苯基胺基、三甲基矽烷基、三乙基矽烷基、三丙基矽烷基、三(第三丁基)矽烷基、第三丁基二甲基矽烷基、二甲基苯基矽烷基、或三苯基矽烷基；a至d各獨立表示1或2，更佳為1；在Ar1、Ar2、R’、及R1至R4中之該取代基各獨立可經至少一個選自下列所組成群組者取代：氘、氯基、氟基、甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、異戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二基、十六基、三氟甲基、 全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、萘基、聯苯基、9,9-二甲基茀基、9,9-二苯基茀基、丙二烯合茀基、聯三伸苯基、芘基、蒯基、稠四苯基、苝基、吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、吡基、嘧啶基、嗒基、喹啉基、三基、苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并噻吩基、吡唑基、吲哚基、咔唑基、N-咔唑基、噻唑基、唑基、苯并噻唑基、苯并唑基、啡啉基、二甲基胺基、二乙基胺基、甲基苯基胺基、二苯基胺基、三甲基矽烷基、三乙基矽烷基、三丙基矽烷基、三(第三丁基)矽烷基、第三丁基二甲基矽烷基、二甲基苯基矽烷基、甲基二苯基矽烷基、三苯基矽烷基、及N-苯基咔唑基。 More specifically, L 1 and L 2 each independently represent a single bond, a phenylene group, a stretched phenyl group, a stretched triphenyl group, a fluorene group, a fluorene group, a stretched triphenyl group, a fluorene group, and a stretch. Sulfhydryl, chrysenylene, tetraphenyl, styrene, thiophene, pyrrolyl, pyrazolyl, thiazolyl, Azolyl Diazolyl, stretched three Base, stretch four , triazole, exofuran, pyridyl, benzofuranyl, benzothiophene, decyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl Benzene Azolyl An azolyl, benzothiadiazolyl, dibenzofuranyl or dibenzothiophenyl group; Ar 1 , Ar 2 and R′ each independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl , n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, fluorenyl, dodecyl, Hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, fluorenyl, fluoranthcnyl, Triphenyl, fluorenyl, fluorenyl, naphthacenyl, fluorenyl, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, benzimidazolyl, quinolyl, tri Base, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, pyrazolyl, fluorenyl, oxazolyl, thiazolyl, Azolyl, benzothiazolyl, benzo Azyl, morpholinyl, quin a phenyl group, or an N-carbazolyl group; each of R 1 to R 4 independently represents hydrogen, deuterium, chloro, fluoro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, Tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecanyl, trifluoromethyl, Perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, anthryl, biphenyl, anthracenyl, allyldienyl, orthotriphenyl , mercapto, fluorenyl, fused tetraphenyl, fluorenyl, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, benzimidazolyl, fluorenyl, pyridyl Base, pyrimidinyl, oxime Base, quinolyl, three Base, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, pyrazolyl, fluorenyl, oxazolyl, thiazolyl, Azolyl, benzothiazolyl, benzo Azyl, morpholinyl, N-carbazolyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethyldecyl, triethyldecyl, Tripropyldecylalkyl, tri(t-butyl)decylalkyl, tert-butyldimethylmethylalkyl, dimethylphenyldecyl, or triphenylsulfanyl; a to d each independently represent 1 or 2 More preferably, the substituents in Ar 1 , Ar 2 , R′, and R 1 to R 4 are each independently substituted by at least one group selected from the group consisting of hydrazine, chloro, and fluoro. ,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-B Hexyl, n-decyl, decyl, dodecyl, hexadecanyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, hydrazine Phenyl, 9,9-dimethylindenyl, 9,9-diphenylindenyl, allyldienyl, triphenylene, anthracenyl, fluorenyl, fused tetraphenyl, fluorenyl, Pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, benzimidazolyl, pyridyl Base, pyrimidinyl, oxime Base, quinolyl, three , benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothienyl, pyrazolyl, fluorenyl, oxazolyl, N-carbazolyl, thiazolyl, Azolyl, benzothiazolyl, benzo Azyl, morpholinyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethyldecyl, triethyldecyl, tripropyldecyl, Tris(t-butyl)decylalkyl, tert-butyldimethylmethylalkyl, dimethylphenyldecyl, methyldiphenyldecyl, triphenyldecyl, and N-phenylcarbazolyl .

本發明之有機電場發光化合物包含下列化合物： The organic electroluminescent compound of the present invention comprises the following compounds:

根據本發明之有機電場發光化合物可依據下列反應方案製備。 The organic electroluminescent compound according to the present invention can be prepared according to the following reaction scheme.

其中，Ar1、Ar2、L1、L2、Y、X1、X2、R1至R4、a、b、c及d係如同上述式(1)般定義，及Hal表示鹵素。 Here, Ar 1 , Ar 2 , L 1 , L 2 , Y, X 1 , X 2 , R 1 to R 4 , a, b, c and d are as defined in the above formula (1), and Hal represents a halogen.

此外，本發明提供包括該式(1)之化合物之有機電場發 光裝置。該有機電場發光裝置包括第一電極、第二電極、以及至少一層插置於該第一電極以及第二電極間的有機層。該有機層包括至少一種依據本發明之式(1)之化合物。再者，該有機層包括至少一種根據本發明式(1)之化合物。 Further, the present invention provides an organic electric field comprising the compound of the formula (1) Optical device. The organic electric field light-emitting device includes a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode. The organic layer comprises at least one compound of the formula (1) according to the invention. Furthermore, the organic layer comprises at least one compound of the formula (1) according to the invention.

該第一電極及該第二電極中之一者係陽極，而另一者係陰極。該有機層包括發光層，及可復包括選自電洞注入層、電洞傳輸層、電子傳輸層、電子注入層、中介層及電洞阻擋層之至少一層。 One of the first electrode and the second electrode is an anode, and the other is a cathode. The organic layer includes 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 injection layer, an interposer layer, and a hole blocking layer.

該式(1)之化合物係包括在該發光層及該電洞傳輸層之至少一者中。於電洞傳輸層中，該式(1)之化合物可作為電洞傳輸材料被包含在內。較佳為，該發光層可復包括至少一種摻雜劑；若有需要，除了包括該式(1)之化合物之外，該發光層可復包括第二種主體材料。 The compound of the formula (1) is included in at least one of the light-emitting layer and the hole transport layer. In the hole transport layer, the compound of the formula (1) can be included as a hole transport material. Preferably, the luminescent layer may further comprise at least one dopant; if desired, the luminescent layer may comprise a second host material in addition to the compound of formula (1).

作為摻雜劑而言，較佳為至少一種磷光摻雜劑。可包括在本發明之有機電場發光裝置中之磷光摻雜劑不特別限於但較佳為選自銥(Ir)、鋨(Os)、銅(Cu)及鉑(Pt)之金屬原子之複合物，更佳為選自Ir、Os、Cu及Pt金屬原子之鄰位金屬化複合物(ortho-metalated complex compound)，及尤佳為鄰位金屬化銥複合物。 As the dopant, at least one phosphorescent dopant is preferred. The phosphorescent dopant which may be included in the organic electroluminescence device of the present invention is not particularly limited, but is preferably a composite of metal atoms selected from the group consisting of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). More preferably, it is an ortho-metalated complex compound selected from the group consisting of Ir, Os, Cu, and Pt metal atoms, and particularly preferably an ortho-metalated ruthenium complex.

磷光摻雜劑係較佳為選自下列式(2)至(4)表示之化合物。 The phosphorescent dopant is preferably a compound selected from the following formulas (2) to (4).

在上揭式(2)至(4)中，L係選自下列結構： In the above formulas (2) to (4), the L system is selected from the following structures:

其中，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R127各獨立氫、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、氰基或經取代或未經取代之(C1-C30)烷氧基；R201至R211各獨立氫、氘、鹵素、未經取代或經鹵素取代之(C1-C30)烷基、或經取代或未經取代之(C3-C30)環烷基；f及g各獨立1至3之整數，及h表示1或2之整數，f至h，其中當每一個f至h係2或更多之整數時，每一個R100係相異或相同；以及n係1至3之整數。 Wherein 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 127 Each of independently hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, cyano or substituted or unsubstituted (C1-C30) alkoxy; R 201 to R 211 each independently hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30) alkyl, or substituted or unsubstituted (C3-C30 a cycloalkyl group; f and g are each an integer from 1 to 3, and h represents an integer of 1 or 2, f to h, wherein each of the R 100 systems is each of f to h when an integer of 2 or more is used. Different or identical; and n is an integer from 1 to 3.

磷光摻雜劑材料包含下列者： Phosphorescent dopant materials include the following:

此外，該有機電場發光裝置包括第一電極、第二電極、以及至少一層插置於該第一電極以及第二電極間的有機層。該有機層包括著包括至少一種依據本發明之用於有機電場發光裝置之組成物及磷光摻雜劑材料之發光層。該用於有機電場發光裝置之組成物係用作為主體材料。 Further, the organic electric field light-emitting device includes a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode. The organic layer includes a light-emitting layer comprising at least one composition for an organic electric field light-emitting device and a phosphorescent dopant material in accordance with the present invention. The composition for an organic electric field light-emitting device is used as a host material.

依據本發明之有機電場發光裝置，除了包括式(1)表示之化合物外，可復包括至少一種選自芳基胺系化合物以及苯乙烯基芳基胺系所組成之化合物。 The organic electroluminescence device according to the present invention may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine system, in addition to the compound represented by the formula (1).

在依據本發明之有機電場發光裝置中，該有機層可復包括選自週期表上第1族之金屬、第2族之金屬、第4週期之過渡金屬、第5週期之過渡金屬、鑭系金屬以及d族過鍍元素之有機金屬所組成群組之至少一種金屬，或包括 至少一種該金屬之錯合物。該有機層可包括發光層以及電荷產生層(charge generating layer)。 In the organic electroluminescence device according to the present invention, the organic layer may further comprise a metal selected from Group 1 of the periodic table, a metal of Group 2, a transition metal of the fourth cycle, a transition metal of the fifth cycle, and a lanthanide system. At least one metal of the group consisting of metal and a group D organic plating metal, or At least one complex of the metal. The organic layer may include a light emitting layer and a charge generating layer.

此外，除了本發明之化合物外，本發明之有機電場發光裝置可藉由復包括至少一層包括藍光電場發光化合物、紅光電場發光化合物或綠光電場發光化合物之發光層而發出白光。此外，於偶發之要求下，該有機電場發光裝置可包括黃光或橘光發光層。 Further, in addition to the compound of the present invention, the organic electroluminescence device of the present invention can emit white light by further including at least one luminescent layer comprising a blue electric field luminescent compound, a red electric field luminescent compound or a green electric field luminescent compound. In addition, the organic electric field light-emitting device may include a yellow or orange light emitting layer at the request of the sporadic.

較佳地，在依據本發明之有機電場發光裝置中，可將至少一層選自硫屬化合物(chalcogenide)層、金屬鹵化物層以及金屬氧化物層之層體(後文中表示「表面層」)放置在單一或兩個電極之一個或多個內表面上。具體而言，較佳為將矽或鋁之硫屬化合物(包含氧化物)層設置於電場發光介質層之陽極表面上，以及將金屬鹵化物層或金屬氧化物層設置於電場發光介質層之陰極表面上。該等表面層提供該有機電場發光裝置之操作安定性。較佳地，該硫屬化合物包含SiOX(1≦X≦2)、AIOX(1≦X≦1.5)、SiON、SiAlON等；該金屬鹵化物包含LiF、MgF2、CaF2、稀土金屬氟化物等；以及該金屬氧化物包含CS2O、Li2O、MgO、SrO、BaO、CaO等。 Preferably, in the organic electric field light-emitting device according to the present invention, at least one layer selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") may be used. Placed on one or more inner surfaces of a single or two electrodes. Specifically, it is preferable to provide a layer of a chalcogen compound (including an oxide) of bismuth or aluminum on the anode surface of the electric field luminescent medium layer, and to provide a metal halide layer or a metal oxide layer on the luminescent medium layer. On the surface of the cathode. The surface layers provide operational stability of the organic electric field illuminating device. Preferably, the chalcogen compound comprises SiO X (1≦X≦2), AIO X (1≦X≦1.5), SiON, SiAlON, etc.; the metal halide comprises LiF, MgF 2 , CaF 2 , rare earth metal fluoride And a metal oxide comprising CS 2 O, Li 2 O, MgO, SrO, BaO, CaO, or the like.

較佳地，在本發明之有機電場發光裝置中，可在電極對之至少一個表面上設置電子傳輸化合物以及還原摻雜劑之混合區，或電洞傳輸化合物以及氧化摻雜劑之混合區。在此例中，將該電子傳輸化合物還原成陰離子，而使得易於自該混合區注入以及傳輸電子至電場發光介質。再者， 將該電洞傳輸化合物氧化成陽離子，而使得易於自該混合區注入以及傳輸電洞至該電場發光介質。較佳地，該氧化性摻雜劑包含多種路易士酸以及接受體化合物；以及該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。可使用還原性摻雜層作為電荷產生層，以製備具有二層或更多層電場發光層且發射白光之電場發光裝置。 Preferably, in the organic electric field light-emitting 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 disposed on at least one surface of the electrode pair. In this case, the electron transporting compound is reduced to an anion, making it easy to inject and transport electrons from the mixing zone to the electric field illuminating medium. Furthermore, The hole transport compound is oxidized to a cation such that it is easy to inject and transport holes from the mixing zone to the electric field luminescent medium. Preferably, the oxidizing dopant comprises a plurality of Lewis acids and a acceptor compound; and the reducing dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, a rare earth metal, and a mixture thereof. A reductive doping layer may be used as the charge generating layer to prepare an electric field light-emitting device having two or more layers of an electroluminescent layer and emitting white light.

後文，將參考下列實施例詳細描述本發明之用於有機電場發光化合物、該化合物之製備方法，以及包括該化合物之裝置的發光特性： Hereinafter, the organic electroluminescent compound, the preparation method of the compound, and the luminescent properties of the device including the compound of the present invention will be described in detail with reference to the following examples:

實施例1：化合物C-52之製備 Example 1: Preparation of Compound C-52

化合物1-1之製備 Preparation of Compound 1-1

將二苯并[b,d]噻吩-4-基硼酸(14克(g)，61毫莫耳(mmol))、3-溴-9H-咔唑(10克，41毫莫耳)及K2CO3(19.1克，138毫莫耳)溶解在混合之甲苯(200毫升)/EtOH(100毫升)/蒸餾水(100毫升)溶液中後，添加Pd(PPh3)4(2.3克，2毫莫耳)。在120℃攪拌該反應混合物5小時，冷卻至室溫，及以EA萃取(800毫升)。以蒸餾水清洗該所得之 有機層(200毫升)，及減壓蒸餾以移除有機溶劑。以甲醇清洗該所得之固體，過濾，乾燥，及以矽膠管柱層析術及再結晶分離以得到化合物1-1(10克，71%)。 Dibenzo[b,d]thiophen-4-ylboronic acid (14 g (g), 61 mmol (mmol)), 3-bromo-9H-carbazole (10 g, 41 mmol) and K 2 CO 3 (19.1 g, 138 mmol) dissolved in a solution of mixed toluene (200 ml) / EtOH (100 ml) / distilled water (100 ml), then added Pd(PPh 3 ) 4 (2.3 g, 2 m Moore). The reaction mixture was stirred at 120 <0>C for 5 h, cooled to rt and EtOAc (EtOAc) The obtained organic layer (200 ml) was washed with distilled water and distilled under reduced pressure to remove organic solvent. The obtained solid was washed with methanol, filtered, dried, and then purified by silica gel column chromatography and recrystallization to afford Compound 1-1 (10 g, 71%).

化合物1-2之製備 Preparation of Compound 1-2

將聯苯-4-基硼酸(50克，250毫莫耳)、1,3-二溴苯(46毫升，380毫莫耳)及Na2CO3(66克，630毫莫耳)溶解在混合之甲苯(700毫升)/EtOH(320毫升)/蒸餾水(320毫升)溶液中後，添加Pd(PPh3)2Cl2(5.6克，8毫莫耳)。在120℃攪拌該反應混合物5小時，冷卻至室溫，及以EA萃取(1.5公升)。以蒸餾水清洗(400毫升)該所得之有機層，及減壓蒸餾以移除有機溶劑。以甲醇清洗該所得之固體，過濾，乾燥，及以矽膠管柱層析術及再結晶分離以得到化合物1-2(28克，56%)。 Dissolve biphenyl-4-ylboronic acid (50 g, 250 mmol), 1,3-dibromobenzene (46 mL, 380 mmol) and Na 2 CO 3 (66 g, 630 mmol) After mixing a solution of toluene (700 ml) / EtOH (320 ml) / distilled water (320 ml), Pd(PPh 3 ) 2 Cl 2 (5.6 g, 8 mmol) was added. The reaction mixture was stirred at 120 ° C for 5 hours, cooled to room temperature and extracted with EA (1.5 liters). The obtained organic layer was washed with distilled water (400 ml), and distilled under reduced pressure to remove organic solvent. The obtained solid was washed with methanol, filtered, dried, and then purified by silica gel column chromatography and recrystallization to afford Compound 1-2 (28 g, 56%).

化合物1-3之製備 Preparation of Compound 1-3

將化合物1-2(20克，65毫莫耳)溶解於THF(350毫升)，及在-78℃添加n-BuLi(2.5M己烷溶液39毫升，97毫莫耳)至該反應混合物後，攪拌該反應混合物1小時。攪拌該反應混合物2小時，伴隨緩慢添加B(OMe)3(11毫升，97毫莫耳)至該反應混合物。以氯化銨水溶液(50毫升)終止該反應後，以EA(1公升)萃取該反應混合物。該所得之有機層以蒸餾水清洗(200毫升)。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除該溶劑。以再結晶分離該所得之固體以得到化合物1-3(14克，79%)。 Compound 1-2 (20 g, 65 mmol) was dissolved in THF (350 mL), and n-BuLi (2.5 M hexanes (39 mL, 97 mM) was added to the reaction mixture at -78 ° C. The reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 h with B (OMe) 3 (11 mL, &lt After quenching the reaction with aqueous ammonium chloride (50 mL), the reaction mixture was extracted with EA (1 liter). The resulting organic layer was washed with distilled water (200 mL). The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture and distilled under reduced pressure to remove the solvent. The obtained solid was separated by recrystallization to give Compound 1-3 (14 g, 79%).

化合物1-4之製備 Preparation of compound 1-4

將化合物1-3(14克，51毫莫耳)、2,4-二氯嘧啶(11克，77毫莫耳)及Na2CO3(13.5克，128毫莫耳)溶解在混合之甲苯(130毫升)/EtOH(65毫升)/蒸餾水(65毫升)溶液中後，添加Pd(PPh3)4(3克，2.6毫莫耳)。在120℃攪拌該反應混合物5小時，冷卻至室溫，及以EA(300毫升)萃取。以蒸餾水(100毫升)清洗該所得之有機層，及減壓蒸餾以移除有機溶劑。以甲醇清洗該所得之固體，過濾，乾燥，及以矽膠管柱層析術及再結晶分離以得到化合物1-4(8克，46%)。 Compound 1-3 (14 g, 51 mmol), 2,4-dichloropyrimidine (11 g, 77 mmol) and Na 2 CO 3 (13.5 g, 128 mmol) were dissolved in mixed toluene After (130 ml) / EtOH (65 ml) / distilled water (65 ml), Pd(PPh 3 ) 4 (3 g, 2.6 mmol) was added. The reaction mixture was stirred at 120 <0>C for 5 h, cooled to rt and EtOAc (EtOAc) The obtained organic layer was washed with distilled water (100 ml), and distilled under reduced pressure to remove organic solvent. The obtained solid was washed with methanol, filtered, dried, and then purified by silica gel column chromatography and recrystallization to afford compound 1-4 (8 g, 46%).

化合物C-52之製備 Preparation of Compound C-52

將化合物1-1(5克，14毫莫耳)溶解於DMF(100毫升)後，伴隨緩慢添加NaH(0.9克，22毫莫耳)攪拌該反應混合物，攪拌30分鐘。將化合物1-4(5.4克，16毫莫耳)溶解於DMF(50毫升)後，將該溶液添加至該反應混合物及攪拌4小時。將該反應混合物添加至蒸餾水(300毫升)伴隨攪拌30分鐘。以再結晶分離該所得之固體以得到化合物C-52(2.4克，26%)。 After dissolving Compound 1-1 (5 g, 14 mmol) in DMF (100 mL), the reaction mixture was stirred with slowly NaH (0.9 g, 22 mmol) and stirred for 30 min. After dissolving Compound 1-4 (5.4 g, 16 mmol) in DMF (50 mL), this solution was added to the reaction mixture and stirred for 4 hr. The reaction mixture was added to distilled water (300 mL) with stirring for 30 min. The obtained solid was separated by recrystallization to give Compound C-52 (2.4 g, 26%).

實施例2：化合物C-54之製備 Example 2: Preparation of Compound C-54

化合物2-1之製備 Preparation of Compound 2-1

將咔唑(25克，149.5毫莫耳)、1,3-二溴苯(57毫升，448.5毫莫耳)、CuI(14.2克，74.7毫莫耳)、伸乙二胺(5毫升，74.7毫莫耳)及K3PO4(95克，448.5毫莫耳)溶解於甲苯(450毫升)後，在120℃回流下攪拌該反應混合物24小時。終止該反應後，以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到化合物2-1(42克，85%)。 Carbazole (25 g, 149.5 mmol), 1,3-dibromobenzene (57 ml, 448.5 mmol), CuI (14.2 g, 74.7 mmol), ethylenediamine (5 ml, 74.7) after mmol) and K 3 PO 4 (95 g, 448.5 mmol) was dissolved in toluene (450 ml), and the reaction mixture was stirred for 24 hours at reflux 120 ℃. After the reaction was terminated, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to give Compound 2-1 (42 g, 85%).

化合物2-2之製備 Preparation of Compound 2-2

將化合物2-1(42克，130.3毫莫耳)溶解於THF(500毫升)後，將該反應混合物冷卻至-78℃。10分鐘後，緩慢添加n-BuLi(67毫升，169.4毫莫耳，2.5M己烷溶液)，及攪拌該反應混合物1小時。然後，緩慢添加B(OMe)3(23毫升，208.5毫莫耳)，及攪拌該反應混合物24小時。終止該反應後，添加1M之HCl，及以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及以MC/己烷再結晶以得到化合物2-2(25克，67%)。 After compound 2-1 (42 g, 130.3 mmol) was dissolved in THF (500 mL), the reaction mixture was cooled to -78. After 10 minutes, n-BuLi (67 mL, 169.4 mmol, 2.5 M hexanes) was slowly added and the mixture was stirred for one hour. Then, B(OMe) 3 (23 ml, 208.5 mmol) was slowly added, and the reaction mixture was stirred for 24 hours. After the reaction was terminated, 1 M HCl was added and the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and recrystallized from MC/hexane to give compound 2-2 (25 g, 67%).

化合物2-3之製備 Preparation of Compound 2-3

將化合物2-2(8.9克，30.9毫莫耳)、2,4-二氯嘧啶(6.9克，46.6毫莫耳)、Pd(PPh3)4(1.8克，1.5毫莫耳)及Na2CO3(8.2克，77毫莫耳)溶解在混合之甲苯(120毫升)/EtOH(40毫升)溶液中後，在120℃攪拌該反應混合物24小時。然後，緩慢添加蒸餾水以終止該反應後，以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘 餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到化合物2-3(7克，63.6%)。 Compound 2-2 (8.9 g, 30.9 mmol), 2,4-dichloropyrimidine (6.9 g, 46.6 mmol), Pd(PPh 3 ) 4 (1.8 g, 1.5 mmol) and Na 2 After dissolving CO 3 (8.2 g, 77 mmol) in a mixture of toluene (120 ml) / EtOH (40 ml), the mixture was stirred at 120 ° C for 24 hours. Then, after the distilled water was slowly added to terminate the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to give Compound 2-3 (7 g, 63.6%).

化合物C-54之製備 Preparation of Compound C-54

將NaH(674毫克，16.8莫耳)溶解於DMF後，攪拌該溶液。將化合物1-1(4.7克，13.5毫莫耳)溶解於DMF後，將該溶液添加至該NaH溶液，及攪拌1小時。將化合物2-3(4克，11.2毫莫耳)溶解於DMF後，攪拌該溶液。然後，將化合物1-1之混合溶液添加至化合物2-3之混合溶液，及在室溫攪拌24小時。終止該反應後，過濾該所得之固體，以EA清洗及透過管柱過濾以得到化合物C-54(4克，44%)。 After dissolving NaH (674 mg, 16.8 mol) in DMF, the solution was stirred. After dissolving Compound 1-1 (4.7 g, 13.5 mmol) in DMF, the solution was added to the NaH solution and stirred for 1 hour. After compound 2-3 (4 g, 11.2 mmol) was dissolved in DMF, the solution was stirred. Then, a mixed solution of the compound 1-1 was added to the mixed solution of the compound 2-3, and stirred at room temperature for 24 hours. After the reaction was quenched, the obtained solid was filtered, washed with EtOAc and filtered to afford compound C-54 (4 g, 44%).

實施例3：化合物C-56之製備 Example 3: Preparation of Compound C-56

化合物3-1之製備 Preparation of Compound 3-1

混合2,4,6-三氯嘧啶(10克，54.51毫莫耳)、苯基硼酸(16.6克，136.29毫莫耳)、Pd(PPh3)4(3.15克，2.72毫莫耳)、2M K2CO3(50毫升)、甲苯(100毫升)及EtOH(30毫升)後，在回流下攪拌該反應混合物。4小時後，將該反應混合物冷卻至室溫，及添加蒸餾水。以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到化合物3-1(7克，48%)。 Mix 2,4,6-trichloropyrimidine (10 g, 54.51 mmol), phenylboronic acid (16.6 g, 136.29 mmol), Pd(PPh 3 ) 4 (3.15 g, 2.72 mmol), 2M After K 2 CO 3 (50 ml), toluene (100 ml) and EtOH (30 ml), the reaction mixture was stirred under reflux. After 4 hours, the reaction mixture was cooled to room temperature and distilled water was added. The reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to give Compound 3-1 (7 g, 48%).

化合物C-56之製備 Preparation of Compound C-56

將NaH(875毫克，21.8毫莫耳)溶解於DMF後，攪拌該溶液。將化合物1-1(5.1克，14.5毫莫耳)溶解於DMF後，將該溶液添加至該NaH溶液，及攪拌1小時。將化合物3-1(4.7克，17.5毫莫耳)溶解於DMF後，攪拌該溶液。然後，將化合物1-1之混合溶液添加至化合物3-1之混合溶液，及在室溫攪拌24小時。終止該反應後，過濾該所得之固體，以EA清洗及透過管柱過濾以得到化合物C-56(4.5克，53%)。 After dissolving NaH (875 mg, 21.8 mmol) in DMF, the solution was stirred. After dissolving Compound 1-1 (5.1 g, 14.5 mmol) in DMF, the solution was added to the NaH solution, and stirred for 1 hour. After dissolving Compound 3-1 (4.7 g, 17.5 mmol) in DMF, the solution was stirred. Then, a mixed solution of the compound 1-1 was added to the mixed solution of the compound 3-1, and stirred at room temperature for 24 hours. After the reaction was quenched, the obtained solid was filtered, washed with EtOAc and filtered to afford compound C-56 (4.5 g, 53%).

實施例4：化合物C-63之製備 Example 4: Preparation of Compound C-63

化合物4-1之製備 Preparation of Compound 4-1

混合化合物1-1(20克，57毫莫耳)、1,3-二溴苯(54克，226毫莫耳)、CuI(5克，28毫莫耳)、K3PO4(36克，169毫莫耳)及甲苯(280毫升)後，在80℃攪拌該反應混合物10分鐘。添加伸乙二胺(3.5毫升，51毫莫耳)後，在140℃攪拌該反應混合物12小時。終止該反應後，以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到 白色固體，化合物4-1(13克，45%)。 Mixed compound 1-1 (20 g, 57 mmol), 1,3-dibromobenzene (54 g, 226 mmol), CuI (5 g, 28 mmol), K 3 PO 4 (36 g) After 169 mmol and toluene (280 mL), the reaction mixture was stirred at 80 ° C for 10 min. After the addition of ethylenediamine (3.5 ml, 51 mmol), the reaction mixture was stirred at 140 ° C for 12 hours. After the reaction was terminated, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, evaporated to remove solvent, and filtered through a column to give a white solid, Compound 4-1 (13 g, 45%).

化合物4-2之製備 Preparation of Compound 4-2

將化合物4-1(13克，25毫莫耳)溶解於THF(125毫升)後，在氮氣氛圍下緩慢添加n-BuLi(13毫升，2.25M己烷溶液)並攪拌該反應混合物。在相同溫度攪拌該反應混合物1小時。然後，在相同溫度緩慢添加B(OMe)3(4.8毫升，42毫莫耳)。加熱該反應混合物至室溫，及攪拌12小時。終止該反應後，以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及再結晶以得到白色固體，化合物4-2(9克，77%)。 After dissolving Compound 4-1 (13 g, 25 mmol) in THF (125 mL), n-BuLi (13 mL, 2.25 M hexanes) was slowly added under a nitrogen atmosphere and the mixture was stirred. The reaction mixture was stirred at the same temperature for 1 hour. Then, B(OMe) 3 (4.8 ml, 42 mmol) was slowly added at the same temperature. The reaction mixture was heated to room temperature and stirred for 12 hours. After the reaction was terminated, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and recrystallized to give a white solid, Compound 4-2 (9 g, 77%).

化合物4-3之製備 Preparation of compound 4-3

混合2,4,6-三氯-1,3,5-三(10.1克，54.51毫莫耳)、苯基硼酸(16.6克，136.29毫莫耳)、Pd(PPh3)4(3.15克，2.72毫莫耳)、2M K2CO3(50毫升)、甲苯(100毫升)及EtOH(30毫升)後，在回流下攪拌該反應混合物。4小時後，將該反應混合物冷卻至室溫，及添加蒸餾水。以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到化合物4-3(7克，48%)。 Mix 2,4,6-trichloro-1,3,5-three (10.1 g, 54.51 mmol), phenylboronic acid (16.6 g, 136.29 mmol), Pd(PPh 3 ) 4 (3.15 g, 2.72 mmol), 2M K 2 CO 3 (50 mL), toluene After (100 ml) and EtOH (30 ml), the reaction mixture was stirred under reflux. After 4 hours, the reaction mixture was cooled to room temperature and distilled water was added. The reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to give compound 4-3 (7 g, 48%).

化合物C-63之製備 Preparation of Compound C-63

混合化合物4-3(4克，15.1毫莫耳)、化合物4-2(8.5克，18.11毫莫耳)、Pd(PPh3)4(872毫克，0.755毫莫耳)、Na2CO3(4.8克，45毫莫耳)、甲苯(76毫升)、EtOH(20毫升)及蒸餾水(20毫升)後，在120℃攪拌該反應混合物12小 時。終止該反應後，以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到化合物C-63(9克，90%)。 Compound 4-3 (4 g, 15.1 mmol), compound 4-2 (8.5 g, 18.11 mmol), Pd(PPh 3 ) 4 (872 mg, 0.755 mmol), Na 2 CO 3 ( After 4.8 g, 45 mmol, toluene (76 ml), EtOH (20 ml) and distilled water (20 ml), the reaction mixture was stirred at 120 ° C for 12 hours. After the reaction was terminated, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to give Compound C-63 (9 g, 90%).

實施例5：化合物C-81之製備 Example 5: Preparation of Compound C-81

化合物5-1之製備 Preparation of Compound 5-1

將1,3-二溴苯(58克，246毫莫耳)、苯基硼酸(20克，164毫莫耳)、Pd(PPh3)4(5.6克，4.8毫莫耳)及Na2CO3(52克，492毫莫耳)溶解在混合之甲苯(1公升)/EtOH(250毫升)溶液中後，在90℃攪拌該反應混合物3小時。然後，緩慢添加蒸餾水以終止該反應後，以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到化合物5-1(26克，70%)。 1,3-Dibromobenzene (58 g, 246 mmol), phenylboronic acid (20 g, 164 mmol), Pd(PPh 3 ) 4 (5.6 g, 4.8 mmol) and Na 2 CO After 3 (52 g, 492 mmol) was dissolved in a mixture of toluene (1 liter) / EtOH (250 ml), the mixture was stirred at 90 ° C for 3 hours. Then, after the distilled water was slowly added to terminate the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to give Compound 5-1 (26 g, 70%).

化合物5-2之製備 Preparation of compound 5-2

將化合物5-1(26克，111毫莫耳)溶解於THF(500毫升)後，將該反應混合物冷卻至-78℃。10分鐘後，緩慢添加n-BuLi(66.6毫升，166.5毫莫耳，2.5M己烷溶液)，及攪拌該反應混合物1小時。然後，緩慢添加B(OMe)3(24.7毫升，222毫莫耳)，及攪拌該反應混合物24小時。終止該反應後，添加1M HCl，及以EA萃取該反應混合物。以 無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及以MC/己烷再結晶以得到化合物5-2(14.3克，65%)。 After compound 5-1 (26 g, 111 mmol) was dissolved in THF (500 mL), the reaction mixture was cooled to -78. After 10 minutes, n-BuLi (66.6 mL, 166.5 mmol, 2.5 M hexanes) was slowly added and the mixture was stirred for 1 hour. Then, B(OMe) 3 (24.7 ml, 222 mmol) was slowly added, and the reaction mixture was stirred for 24 hours. After the reaction was terminated, 1 M HCl was added and the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and recrystallized from MC/hexane to give compound 5-2 (14.3 g, 65%).

化合物5-3之製備 Preparation of compound 5-3

將化合物5-2(14.3克，72毫莫耳)、1-碘-4-溴苯(30.6克，108.3毫莫耳)、Pd(PPh3)4(3.3克，2.9毫莫耳)及Na2CO3(22.9克，216毫莫耳)溶解在混合之甲苯(500毫升)/EtOH(120毫升)溶液中後，在120℃攪拌該反應混合物24小時。然後，緩慢添加蒸餾水以終止該反應後，以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到化合物5-3(20克，90%)。 Compound 5-2 (14.3 g, 72 mmol), 1-iodo-4-bromobenzene (30.6 g, 108.3 mmol), Pd(PPh 3 ) 4 (3.3 g, 2.9 mmol) and Na After 2 CO 3 (22.9 g, 216 mmol) was dissolved in a mixture of toluene (500 ml) / EtOH (120 ml), the mixture was stirred at 120 ° C for 24 hours. Then, after the distilled water was slowly added to terminate the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to give compound 5-3 (20 g, 90%).

化合物5-4之製備 Preparation of compound 5-4

將化合物5-3(25克，80.8毫莫耳)溶解於THF(610毫升)後，將該反應混合物冷卻至-78℃。10分鐘後，緩慢添加n-BuLi(48.5毫升，121.2毫莫耳，2.5M己烷溶液)，及攪拌該反應混合物1小時。然後，緩慢添加B(OMe)3(18毫升，161.7毫莫耳)，及攪拌該反應混合物24小時。終止該反應後，添加1M HCl，及以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及以MC/己烷再結晶以得到化合物5-4(16克，73%)。 After dissolving compound 5-3 (25 g, 80.8 mmol) in THF (610 mL), the reaction mixture was cooled to -78. After 10 minutes, n-BuLi (48.5 mL, 121.2 mmol, 2.5 M hexanes) was slowly added and the mixture was stirred for one hour. Then, B(OMe) 3 (18 ml, 161.7 mmol) was added slowly, and the reaction mixture was stirred for 24 hours. After the reaction was terminated, 1 M HCl was added and the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and recrystallized from MC/hexane to give compound 5-4 (16 g, 73%).

化合物5-5之製備 Preparation of compound 5-5

將化合物5-4(16克，58.3毫莫耳)、2,4-二氯嘧啶 (11.3克，75.8毫莫耳)、Pd(PPh3)4(3.4克，2.91毫莫耳)及Na2CO3(15.4克，146毫莫耳)溶解在混合之甲苯(300毫升)/EtOH(70毫升)溶液中後，在120℃攪拌該反應混合物24小時。然後，緩慢添加蒸餾水以終止該反應後，以EA萃取該反應混合物。以無水MgSO4乾燥該所得之有機層以移除該殘餘濕氣，減壓蒸餾以移除溶劑，及透過管柱過濾以得到化合物5-5(10克，50%)。 Compound 5-4 (16 g, 58.3 mmol), 2,4-dichloropyrimidine (11.3 g, 75.8 mmol), Pd(PPh 3 ) 4 (3.4 g, 2.91 mmol) and Na 2 After dissolving CO 3 (15.4 g, 146 mmol) in a mixture of toluene (300 ml) / EtOH (70 ml), the mixture was stirred at 120 ° C for 24 hours. Then, after the distilled water was slowly added to terminate the reaction, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO 4 to remove the residual moisture, distilled under reduced pressure to remove solvent, and filtered through a column to give compound 5-5 (10 g, 50%).

化合物C-81之製備 Preparation of Compound C-81

將NaH(875毫克，21.8毫莫耳)溶解於DMF後，攪拌該溶液。將化合物1-1(5克，14.5毫莫耳)溶解於DMF後，將該溶液添加至該NaH溶液，及攪拌1小時。將化合物5-5(6.11克，17.5毫莫耳)溶解於DMF後，攪拌該溶液。然後，將化合物1-1之混合溶液添加至化合物5-5之混合溶液，及攪拌24小時。終止該反應後，過濾該所得之固體，以EA清洗，及透過管柱過濾以得到化合物C-81(5克，53%)。 After dissolving NaH (875 mg, 21.8 mmol) in DMF, the solution was stirred. After dissolving Compound 1-1 (5 g, 14.5 mmol) in DMF, the solution was added to the NaH solution and stirred for 1 hour. After compound 5-5 (6.11 g, 17.5 mmol) was dissolved in DMF, the solution was stirred. Then, a mixed solution of the compound 1-1 was added to the mixed solution of the compound 5-5, and stirred for 24 hours. After the reaction was terminated, the obtained solid was filtered, washed with EA, and filtered through a column to give Compound C-81 (5 g, 53%).

實施例6：化合物C-104之製備 Example 6: Preparation of Compound C-104

化合物6-1之製備 Preparation of Compound 6-1

將二苯并[b,d]噻吩-4-基硼酸(30克，130毫莫耳)、3-溴碘苯(34毫升，260毫莫耳)、Na2CO3(41克，390毫莫 耳)及Pd(PPh3)4(7.5克，6.5毫莫耳)溶解在混合之甲苯(300毫升)/EtOH(100毫升)/純水(100毫升)溶液中後，在100℃攪拌該反應混合物3小時。終止該反應後，將該反應混合物冷卻至室溫，及靜置以移除該水層。濃縮該油層，將之與MC研磨，及過濾以得到化合物6-1(33克，74%)。 Dibenzo[b,d]thiophen-4-ylboronic acid (30 g, 130 mmol), 3-bromoiodobenzene (34 ml, 260 mmol), Na 2 CO 3 (41 g, 390 m) Mol) and Pd(PPh 3 ) 4 (7.5 g, 6.5 mmol) dissolved in a solution of mixed toluene (300 ml) / EtOH (100 ml) / purified water (100 ml), then stirred at 100 ° C The reaction mixture was held for 3 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature and allowed to stand to remove the aqueous layer. The oil layer was concentrated, triturated with MC and filtered to give compound 6-1 (33 g, 74%).

化合物6-2之製備 Preparation of compound 6-2

將化合物6-1(33克，96毫莫耳)溶解於THF(650毫升)，及在-78℃添加n-BuLi(2.5M己烷溶液50毫升，125毫莫耳)至該反應混合物後，攪拌該反應混合物1小時。攪拌該反應混合物2小時，伴隨緩慢添加B(Oi-Pr)3(35毫升，154毫莫耳)至該反應混合物。伴隨添加2M HCl停止反應後，以蒸餾水及EA萃取該反應混合物，及以MC及己烷再結晶以得到化合物6-2(22克，76%)。 Compound 6-1 (33 g, 96 mmol) was dissolved in THF (650 mL) and n-BuLi (2.5M hexanes 50 mL, 125 mM) was added to the reaction mixture at -78 °C. The reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with the slow addition of B(Oi-Pr) 3 (35 mL, 154 mmol) to the reaction mixture. After the reaction was stopped with the addition of 2M HCl, the reaction mixture was extracted with distilled water and EA, and recrystallized from MC and hexane to afford compound 6-2 (22 g, 76%).

化合物6-3之製備 Preparation of Compound 6-3

將化合物6-2(17克，55毫莫耳)、3-溴咔唑(13毫升，55毫莫耳)、K2CO3(23克，163毫莫耳)及Pd(PPh3)4(3克，2.7毫莫耳)溶解在混合之甲苯(300毫升)/EtOH(100毫升)/純水(100毫升)溶液中後，在100℃攪拌該反應混合物3小時。終止該反應後，將該反應混合物冷卻至室溫，及靜置以移除該水層。濃縮該油層，將之與MC研磨，及過濾以得到化合物6-3(14克，62%)。 Compound 6-2 (17 g, 55 mmol), 3-bromocarbazole (13 ml, 55 mmol), K 2 CO 3 (23 g, 163 mmol) and Pd(PPh 3 ) 4 (3 g, 2.7 mmol) After dissolving in a mixture of toluene (300 ml) / EtOH (100 ml) / purified water (100 ml), the reaction mixture was stirred at 100 ° C for 3 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature and allowed to stand to remove the aqueous layer. The oil layer was concentrated, triturated with MC, and filtered to give compound 6-3 (14 g, 62%).

化合物C-104之製備 Preparation of Compound C-104

將化合物6-3(5克，12毫莫耳)及2-氯基-4,6-二苯基-1,3,5-三(3.2克，12毫莫耳)分散於DMF(57毫升)後， 在室溫添加60% NaH(684毫克，17.1毫莫耳)，及攪拌該反應混合物12小時。添加純水(1公升)後，減壓下過濾該反應混合物。將該所得之固體與MeOH/EA研磨，以MC溶解，透過氣化矽過濾，及將之與MC/正己烷研磨以得到化合物104(1.7克，22%)。 Compound 6-3 (5 g, 12 mmol) and 2-chloro-4,6-diphenyl-1,3,5-three (3.2 g, 12 mmol) After dispersing in DMF (57 mL), 60% NaH (684 mg, 17.1 mmol) was added at room temperature and the mixture was stirred for 12 hours. After adding pure water (1 liter), the reaction mixture was filtered under reduced pressure. The resulting solid was triturated with MeOH / EtOAc, EtOAc (EtOAc) EtOAc (EtOAc)

其他可依據上揭實施例1至6輕易製備之化合物數據係列於表1。 Other compound data series which can be easily prepared according to the above-mentioned Examples 1 to 6 are shown in Table 1.

試驗例1：使用本發明之化合物之OLED裝置之製備 Test Example 1: Preparation of an OLED device using the compound of the present invention

使用本發明之化合物製備OLED裝置。使用超音波依序以三氯乙烯、丙酮、乙醇以及蒸餾水清洗用於有機發光二極體(OLED)裝置(Samsung Corning，大韓民國)之玻璃基材上的透明電極銦錫氧化物(ITO)薄膜(15 Ω/sq)，然後儲存在異丙醇中。之後，將該ITO基材裝設在真空氣相沉積裝置之基板夾持器上。將N1,N1’-([1,1’-聯苯]-4,4’-二基)雙(N1-(萘-1-基)-N4,N4-二苯基苯-1,4-二胺)導入該真空氣相沉積裝置之小室(cell)中，然後控制該裝置之腔室之壓力達10-6托耳(torr)。之後，對該小室施加電流以蒸發該導入之材料，藉以在該ITO基材上形成具有60nm厚度之電洞注入層。之後，將N,N’-二(4-聯苯基)-N,N’-二(4-聯苯基)-4,4’-二胺基聯苯導入該真空氣相沉積裝置之另一個小室，以及藉由對該小室施加電流使之蒸發，藉以在該電洞注入層上形成具有20nm厚度之電洞傳輸層。之後，將化合物C-42導入該真空氣相沉積裝置之一個小室中作為主體材料，以及將化合物D-48導入另一個小室作為摻雜劑。將該兩種材料以不同速率蒸發而以15wt%之摻雜量沉積，以在該電洞傳輸層上形成具有30nm厚度之發光層。之後，將2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑導入一個小室以及將8-羥基喹啉鋰(lithium quinolate)導入另一個小室中。將該兩種材料以相同速率蒸發而以50wt%之摻雜量沉積，以在該發光層上形成具有30nm厚度之電子傳輸層。之後，在沉積具有2nm 厚度之8-羥基喹啉鋰作為該電子傳輸層上的電子注入層後，藉由另一個真空氣相沉積裝置將具有150nm厚度之Al陰極沉積在該電子注入層上。因而製得OLED裝置。用於製造該OLED裝置之所有材料皆已於使用前藉由10-6torr之真空昇華而純化。 An OLED device is prepared using the compounds of the invention. A transparent electrode indium tin oxide (ITO) film for use on a glass substrate of an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was washed with a mixture of trichloroethylene, acetone, ethanol, and distilled water using ultrasonic waves ( 15 Ω/sq) and then stored in isopropanol. Thereafter, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. N 1 ,N 1 ' -([1,1'-biphenyl]-4,4'-diyl) bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene -1,4-Diamine) is introduced into the cell of the vacuum vapor deposition apparatus, and then the pressure of the chamber of the apparatus is controlled to 10 -6 torr. Thereafter, a current was applied to the chamber to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Thereafter, N,N'-bis(4-biphenyl)-N,N'-bis(4-biphenyl)-4,4'-diaminobiphenyl is introduced into the vacuum vapor deposition apparatus. A cell, and by applying a current to the cell to evaporate, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, the compound C-42 was introduced into one chamber of the vacuum vapor deposition apparatus as a host material, and the compound D-48 was introduced into another chamber as a dopant. The two materials were evaporated at different rates and deposited at a doping amount of 15% by weight to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Thereafter, 2-(4-(9,10-di(naphthalen-2-yl)indol-2-yl)phenyl)-1-phenyl-1H-benzo[ d ]imidazole is introduced into a chamber and 8 Lithium quinolate is introduced into another chamber. The two materials were evaporated at the same rate and deposited at a doping amount of 50% by weight to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Thereafter, after depositing lithium hydroxyquinolate having a thickness of 2 nm as an electron injecting layer on the electron transporting layer, an Al cathode having a thickness of 150 nm was deposited on the electron injecting layer by another vacuum vapor deposition apparatus. Thus an OLED device is produced. All materials used to make the OLED device were purified by vacuum sublimation of 10 -6 torr prior to use.

該製得之OLED裝置在驅動電壓4.4 V顯示具有發光度為1000 cd/m2及電流密度為2.17 mA/cm2之綠光發光。 The obtained OLED device showed green light emission having a luminance of 1000 cd/m 2 and a current density of 2.17 mA/cm 2 at a driving voltage of 4.4 V.

試驗例2：使用本發明之化合物之OLED裝置之製備 Test Example 2: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-44作為主體材料，及化合物D-1作為摻雜劑。該製得之OLED裝置在驅動電壓3.1 V顯示具有發光度為2030 cd/m2及電流密度為4.39 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-44 was used as a host material, and the compound D-1 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 2030 cd/m 2 and a current density of 4.39 mA/cm 2 at a driving voltage of 3.1 V.

試驗例3：使用本發明之化合物之OLED裝置之製備 Test Example 3: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-52作為主體材料，及化合物D-9作為摻雜劑。該製得之OLED裝置在驅動電壓3.5 V顯示具有發光度為1000 cd/m2及電流密度為2.35 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-52 was used as a host material, and the compound D-9 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 1000 cd/m 2 and a current density of 2.35 mA/cm 2 at a driving voltage of 3.5 V.

試驗例4：使用本發明之化合物之OLED裝置之製備 Test Example 4: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-54作為主體材料，及化合物D-1作為摻雜劑。該製得之OLED裝置在驅動電壓3.8 V顯示具有發光度為1050 cd/m2及電流密度為2.21 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-54 was used as a host material, and the compound D-1 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 1050 cd/m 2 and a current density of 2.21 mA/cm 2 at a driving voltage of 3.8 V.

試驗例5：使用本發明之化合物之OLED裝置之製備 Test Example 5: Preparation of OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用 化合物C-56作為主體材料，及化合物D-1作為摻雜劑。該製得之OLED裝置在驅動電壓2.7 V顯示具有發光度為1510 cd/m2及電流密度為3.41 mA/cm2之橘光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-56 was used as a host material, and the compound D-1 was used as a dopant. The obtained OLED device showed orange light emission having a luminance of 1510 cd/m 2 and a current density of 3.41 mA/cm 2 at a driving voltage of 2.7 V.

試驗例6：使用本發明之化合物之OLED裝置之製備 Test Example 6: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-57作為主體材料，及化合物D-48作為摻雜劑。該製得之OLED裝置在驅動電壓4.1 V顯示具有發光度為2160 cd/m2及電流密度為5.65 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that Compound C-57 was used as a host material, and Compound D-48 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 2160 cd/m 2 and a current density of 5.65 mA/cm 2 at a driving voltage of 4.1 V.

試驗例7：使用本發明之化合物之OLED裝置之製備 Test Example 7: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-59作為主體材料，及化合物D-48作為摻雜劑。該製得之OLED裝置在驅動電壓3.8 V顯示具有發光度為1470 cd/m2及電流密度為3.56 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that Compound C-59 was used as a host material, and Compound D-48 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 1470 cd/m 2 and a current density of 3.56 mA/cm 2 at a driving voltage of 3.8 V.

試驗例8：使用本發明之化合物之OLED裝置之製備 Test Example 8: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-61作為主體材料，及化合物D-9作為摻雜劑。該製得之OLED裝置在驅動電壓2.7 V顯示具有發光度為1130 cd/m2及電流密度為2.69 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-61 was used as a host material, and the compound D-9 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 1130 cd/m 2 and a current density of 2.69 mA/cm 2 at a driving voltage of 2.7 V.

試驗例9：使用本發明之化合物之OLED裝置之製備 Test Example 9: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-62作為主體材料，及化合物D-1作為摻雜劑。該製得之OLED裝置在驅動電壓2.6 V顯示具有發光度為890 cd/m2及電流密度為2.51 mA/cm2之橘光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-62 was used as a host material, and the compound D-1 was used as a dopant. The obtained OLED device showed orange light emission having a luminance of 890 cd/m 2 and a current density of 2.51 mA/cm 2 at a driving voltage of 2.6 V.

試驗例10：使用本發明之化合物之OLED裝置之製備 Test Example 10: Preparation of OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-68作為主體材料，及化合物D-48作為摻雜劑。該製得之OLED裝置在驅動電壓2.6 V顯示具有發光度為1100 cd/m2及電流密度為3.98 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that Compound C-68 was used as a host material, and Compound D-48 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 1100 cd/m 2 and a current density of 3.98 mA/cm 2 at a driving voltage of 2.6 V.

試驗例11：使用本發明之化合物之OLED裝置之製備 Test Example 11: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-81作為主體材料，及化合物D-1作為摻雜劑。該製得之OLED裝置在驅動電壓3.0 V顯示具有發光度為1070 cd/m2及電流密度為2.60 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-81 was used as a host material, and the compound D-1 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 1070 cd/m 2 and a current density of 2.60 mA/cm 2 at a driving voltage of 3.0 V.

試驗例12：使用本發明之化合物之OLED裝置之製備 Test Example 12: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-100作為主體材料，及化合物D-48作為摻雜劑。該製得之OLED裝置在驅動電壓4.9 V顯示具有發光度為4210 cd/m2及電流密度為9.29 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-100 was used as a host material, and the compound D-48 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 4210 cd/m 2 and a current density of 9.29 mA/cm 2 at a driving voltage of 4.9 V.

試驗例13：使用本發明之化合物之OLED裝置之製備 Test Example 13: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-101作為主體材料，及化合物D-1作為摻雜劑。該製得之OLED裝置在驅動電壓4.0 V顯示具有發光度為3630 cd/m2及電流密度為9.75 mA/cm2之橘光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-101 was used as a host material, and the compound D-1 was used as a dopant. The obtained OLED device showed orange light emission having a luminance of 3,630 cd/m 2 and a current density of 9.75 mA/cm 2 at a driving voltage of 4.0 V.

試驗例14：使用本發明之化合物之OLED裝置之製備 Test Example 14: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-102作為主體材料，及化合物D-1作為摻雜劑。該製得之OLED裝置在驅動電壓3.7 V顯示具有發光度為1870 cd/m2及電流密度為4.00 mA/cm2之綠光發光。 An OLED device was prepared in the same manner as in Example 1, except that Compound C-102 was used as a host material, and Compound D-1 was used as a dopant. The obtained OLED device showed green light emission having a luminance of 1870 cd/m 2 and a current density of 4.00 mA/cm 2 at a driving voltage of 3.7 V.

試驗例15：使用本發明之化合物之OLED裝置之製備 Test Example 15: Preparation of an OLED device using the compound of the present invention

使用與實施例1相同之方式製備OLED裝置，除了使用化合物C-104作為主體材料，及化合物D-9作為摻雜劑。該製得之OLED裝置在驅動電壓2.6 V顯示具有發光度為1010 cd/m2及電流密度為2.42 mA/cm2之橘光發光。 An OLED device was prepared in the same manner as in Example 1, except that the compound C-104 was used as a host material, and the compound D-9 was used as a dopant. The obtained OLED device showed orange light emission having a luminance of 1010 cd/m 2 and a current density of 2.42 mA/cm 2 at a driving voltage of 2.6 V.

比較例1：使用傳統電場發光化合物之OLED裝置之製備 Comparative Example 1: Preparation of an OLED device using a conventional electroluminescent compound

使用與實施例1相同之方式製備OLED裝置，除了沉積在該電洞傳輸層具有30nm厚度之發光層改成使用4,4’-N,N’-二咔唑-聯苯(CBP)作為主體材料以及Ir(ppy)3作為摻雜劑以及藉由使用雙(2-甲基-8-羥基喹啉)-4-苯基酚鋁(III)沉積具有10nm厚度之電洞阻擋層。 An OLED device was prepared in the same manner as in Example 1, except that a light-emitting layer having a thickness of 30 nm deposited on the hole transport layer was changed to use 4,4'-N,N'-dicarbazole-biphenyl (CBP) as a main body. The material and Ir(ppy) 3 were used as dopants and a hole blocking layer having a thickness of 10 nm was deposited by using bis(2-methyl-8-hydroxyquinoline)-4-phenylphenol aluminum (III).

該製得之OLED裝置在驅動電壓4.8 V顯示具有發光度為1000 cd/m2及電流密度為2.89 mA/cm2之綠光發光。 The obtained OLED device showed green light emission having a luminance of 1000 cd/m 2 and a current density of 2.89 mA/cm 2 at a driving voltage of 4.8 V.

本發明之化合物相較於傳統材料具有優越之發光特性。此外，使用本發明之化合物作為綠光或橘光發光之主體材料之裝置不僅具有優越之發光特性，亦藉由減低驅動電壓而得到增加之功率效率。 The compounds of the present invention have superior luminescent properties compared to conventional materials. Further, the apparatus using the compound of the present invention as a host material for green light or orange light emission not only has superior light-emitting characteristics, but also has increased power efficiency by reducing the driving voltage.

Claims (6)

一種化合物，其以下式(1)表示： 其中，L1及L2各獨立表示單鍵、經取代或未經取代之3至30員伸雜芳基、經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之(C6-C30)伸環烷基；X1及X2各獨立表示CR’或N；Y表示-O-、-S-、-CR5R6-或-NR7-；Ar1、Ar2及R’各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、或經取代或未經取代之3至30員雜芳基；R1至R4各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3至30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5至7員雜環烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰 基、硝基、或羥基；或該R1至R4鍵結至相鄰之一個或多個取代基以形成單環或多環之(C5-C30)脂環或芳香環，且該環上之一個或多個碳原子可經至少一個選自氮、氧及硫之雜原子置換；R5至R7及R11至R17各獨立表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之3至30員雜芳基、經取代或未經取代之5至7員雜環烷基、或經取代或未經取代之(C3-C30)環烷基；或該R5至R7及R11至R17鍵結至相鄰之一個或多個取代基以形成單環或多環之(C5-C30)脂環或芳香環，且該環上之一個或多個碳原子可經至少一個選自氮、氧及硫之雜原子置換；a及c各獨立表示1至4之整數；當其中a或c係2或更多之整數時，每一個R1或每一個R3係相同或相異；b及d各獨立表示1至3之整數；當其中b或d係2或更多之整數時，每一個R2或每一個R4係相同或相異；以及該伸雜芳基、該雜環烷基及該雜芳基含有至少一個選自B、N、O、S、P(=O)、Si及P之雜原子。 A compound represented by the following formula (1): Wherein, L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted 3 to 30 membered heteroaryl group, a substituted or unsubstituted (C6-C30) extended aryl group, or a substituted or unsubstituted group. Substituted (C6-C30)cycloalkylene; X 1 and X 2 each independently represent CR' or N; Y represents -O-, -S-, -CR 5 R 6 - or -NR 7 -; Ar 1 And Ar 2 and R′ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or not Substituted 3 to 30 membered heteroaryl; R 1 to R 4 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6- C30) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted (C3-C20)cycloalkyl, substituted or unsubstituted 5 to 7 membered heterocycloalkane (C6-C30) aryl (C1-C30) alkyl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , cyano, nitrate Or a hydroxyl group; or the R 1 to R 4 are bonded to one or more adjacent substituents to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and One or more carbon atoms of the ring may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; R 5 to R 7 and R 11 to R 17 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted Substituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted 5 to a 7-membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group; or the R 5 to R 7 and R 11 to R 17 bonded to one or more adjacent substituents Forming a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and one or more carbon atoms of the ring may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; An integer representing from 1 to 4; when a or c is an integer of 2 or more, each R 1 or each R 3 is the same or different; b and d each independently represent an integer from 1 to 3; When b or d is an integer of 2 or more, each R 2 or each R 4 is the same or different; and the heteroaryl group, the heterocycloalkyl group and the heteroaryl group contain at least one selected from the group consisting of B , N, O, S, P (= O), Si and P heteroatoms. 如申請專利範圍第1項所述之化合物，其中，L1、L2、R’、Ar1、Ar2、R1至R4、R5至R7及R11至R17基團中之該經取代之烷基、經取代之(伸)芳基、經取代之(伸)雜芳基、經取代之(伸)環烷基、經取代之雜環烷基、及經取代之芳烷基之取代基各獨立選自下列所組成群組之至 少一者：氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C6-C30)芳基取代或未經取代之3至30員雜芳基、(C3-C30)環烷基、5至7員雜環烷基、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、(C2-C30)烯基、(C2-C30)炔基、氰基、N-咔唑基、二(C1-C30)烷基胺基、二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基、二(C6-C30)芳基硼羰基、二(C1-C30)烷基硼羰基、(C1-C30)烷基(C6-C30)芳基硼羰基、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、羧基、硝基、以及羥基。 The compound according to claim 1, wherein L 1 , L 2 , R′, Ar 1 , Ar 2 , R 1 to R 4 , R 5 to R 7 and R 11 to R 17 are the same. Substituted alkyl, substituted (extended) aryl, substituted (extended) heteroaryl, substituted (extended) cycloalkyl, substituted heterocycloalkyl, and substituted aralkyl The substituents are each independently selected from at least one of the group consisting of hydrazine, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, via (C6- C30) aryl substituted or unsubstituted 3 to 30 membered heteroaryl, (C3-C30)cycloalkyl, 5 to 7 membered heterocycloalkyl, tris(C1-C30)alkyldecane, tris(C6) -C30) arylalkyl, di(C1-C30)alkyl(C6-C30)aryldecyl, (C1-C30)alkylbis(C6-C30)aryldecyl,(C2-C30)ene , (C2-C30)alkynyl, cyano, N-carbazolyl, bis(C1-C30)alkylamino, bis(C6-C30)arylamino, (C1-C30)alkyl (C6 -C30) arylamino group, di(C6-C30) aryl boroncarbonyl group, di(C1-C30)alkyl boroncarbonyl group, (C1-C30)alkyl (C6-C30) aryl boroncarbonyl group, (C6- C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl , carboxyl, nitro, and hydroxyl. 如申請專利範圍第1項所述之化合物，其中，L1及L2各獨立表示單鍵、3至30員伸雜芳基、或(C6-C30)伸芳基；X1及X2各獨立表示CR’或N；Y表示-O-、-S-、-CR5R6-或-NR7-；Ar1、Ar2及R’各獨立表示氫、(C1-C30)烷基、(C6-C30)芳基、或3至30員雜芳基；R1至R4各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、3至30員雜芳基、-NR11R12，或-SiR13R14R15；或R3鍵結至相鄰之一個或多個取代基以形成單環或多環之(C5-C30)脂環或芳香環，且該環上之一個或多個碳原子可經至少一個選自氮、氧及硫之雜原子置換； R5至R7及R11至R17各獨立表示氫、氘、鹵素、(C1-C30)烷基、(C6-C30)芳基、或3至30員雜芳基；以及L1及L2之該伸芳基及伸雜芳基，及Ar1、Ar2、R’、R1至R4、R5至R7及R11至R17該中之該烷基、芳基、及雜芳基各獨立可經至少一個選自下列所組成群組者之取代：氘、鹵素、經鹵素取代或未經取代之(C1-C30)烷基、(C6-C30)芳基、經(C6-C30)芳基取代或未經取代之3至30員雜芳基、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、N-咔唑基、二(C1-C30)烷基胺基、二(C6-C30)芳基胺基、(C1-C30)烷基(C6-C30)芳基胺基；以及(C1-C30)烷基(C6-C30)芳基。 The compound according to claim 1, wherein each of L 1 and L 2 independently represents a single bond, a 3 to 30 member heteroaryl group, or a (C6-C30) extended aryl group; each of X 1 and X 2 Independently denotes CR' or N; Y represents -O-, -S-, -CR 5 R 6 - or -NR 7 -; Ar 1 , Ar 2 and R' each independently represent hydrogen, (C1-C30) alkyl, (C6-C30) aryl, or 3 to 30 membered heteroaryl; R 1 to R 4 each independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30)aryl, 3 to 30 a heteroaryl group, -NR 11 R 12 , or -SiR 13 R 14 R 15 ; or R 3 bonded to one or more adjacent substituents to form a monocyclic or polycyclic (C5-C30) alicyclic ring Or an aromatic ring, and one or more carbon atoms of the ring may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; R 5 to R 7 and R 11 to R 17 each independently represent hydrogen, deuterium, halogen , (C1-C30)alkyl, (C6-C30)aryl, or 3 to 30 membered heteroaryl; and the aryl and heteroaryl of L 1 and L 2 , and Ar 1 , Ar 2 , R', R 1 to R 4 , R 5 to R 7 and R 11 to R 17 wherein the alkyl group, the aryl group and the heteroaryl group are each independently substituted by at least one selected from the group consisting of : 氘, halogen a halogen-substituted or unsubstituted (C1-C30) alkyl group, a (C6-C30) aryl group, a (C6-C30) aryl group substituted or unsubstituted 3 to 30 membered heteroaryl group, three (C1) -C30)alkylalkylalkyl, tris(C6-C30)aryldecylalkyl, di(C1-C30)alkyl(C6-C30)aryldecylalkyl,(C1-C30)alkyldi(C6-C30) Arylalkylene, N-carbazolyl, bis(C1-C30)alkylamino, bis(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamine; And (C1-C30)alkyl (C6-C30) aryl. 如申請專利範圍第1項所述之化合物，其中，L1及L2各獨立表示單鍵、伸苯基、伸聯苯基、伸聯三苯基、伸茚基、伸茀基、伸聯伸三苯基、伸芘基、伸苝基、伸蒯基、伸稠四苯基、伸丙二烯合茀基、伸噻吩基、伸吡咯基、伸吡唑基、伸噻唑基、伸唑基、伸二唑基、伸三基、伸四基、伸三唑基、伸呋吖基、伸吡啶基、伸苯并呋喃基、伸苯并噻吩基、伸吲哚基、伸苯并咪唑基、伸苯并噻唑基、伸苯并異噻唑基、伸苯并異唑基、伸苯并唑基、伸苯并噻二唑基、伸二苯并呋喃基、或伸二苯并噻吩基；Ar1、Ar2及R’各獨立表示氫、甲基、乙基、正丙基、 異丙基、正丁基、異丁基、第三丁基、正戊基、異戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二基、十六基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、聯苯基、茀基、丙二烯合茀基、聯三苯基、芘基、蒯基、稠四苯基、苝基、吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、喹啉基、三基、苯并呋喃基、二苯并呋喃基、苯并噻吩基、二苯并噻吩基、吡唑基、吲哚基、咔唑基、噻唑基、唑基、苯并噻唑基、苯并唑基、啡啉基、喹啉基、或N-咔唑基；R1至R4各獨立表示氫、氘、氯基、氟基、甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、異戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二基、十六基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、萘基、蒽基、聯苯基、茀基、丙二烯合茀基、聯伸三苯基、芘基、蒯基、稠四苯基、苝基、吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、茚基、吡基、嘧啶基、嗒基、喹啉基、三基、苯并呋喃基、二苯并呋喃基、苯并噻吩基、二苯并噻吩基、吡唑基、吲哚基、咔唑基、噻唑基、唑基、苯并噻唑基、苯并唑基、啡啉基、N-咔唑基、二甲基胺基、二乙基胺基、甲基苯基胺基、二苯基胺基、三甲基矽烷基、三乙基矽烷基、三丙基矽烷基、三(第三丁基)矽烷基、第三丁基二甲基矽烷基、 二甲基苯基矽烷基、或三苯基矽烷基；a至d各獨立表示1或2；Ar1、Ar2、R’及R1至R4中之該取代基各獨立可經至少一個選自下列所組成群組者取代：氘、氯基、氟基、甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基、正戊基、異戊基、正己基、正庚基、正辛基、2-乙基己基、正壬基、癸基、十二基、十六基、三氟甲基、全氟乙基、三氟乙基、全氟丙基、全氟丁基、苯基、萘基、聯苯基、9,9-二甲基茀基、9,9-二苯基茀基、丙二烯合茀基、聯伸三苯基、芘基、蒯基、稠四苯基、苝基、吡啶基、吡咯基、呋喃基、噻吩基、咪唑基、苯并咪唑基、吡基、嘧啶基、嗒基、喹啉基、三基、苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并噻吩基、吡唑基、吲哚基、咔唑基、N-咔唑基、噻唑基、唑基、苯并噻唑基、苯并唑基、啡啉基、二甲基胺基、二乙基胺基、甲基苯基胺基、二苯基胺基、三甲基矽烷基、三乙基矽烷基、三丙基矽烷基、三(第三丁基)矽烷基、第三丁基二甲基矽烷基、二甲基苯基矽烷基、甲基二苯基矽烷基、三苯基矽烷基、及N-苯基咔唑基。 The compound according to claim 1, wherein each of L 1 and L 2 independently represents a single bond, a phenyl group, a phenyl group, a ternary triphenyl group, a fluorene group, a hydrazine group, and a hydrazine group. Stretching triphenyl, hydrazine, hydrazine, hydrazine, tetraphenyl, styrene, thiophene, thiazole, pyrazolyl, thiazolyl, Azolyl Diazolyl, stretched three Base, stretch four , triazole, exofuran, pyridyl, benzofuranyl, benzothiophene, decyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl Benzene Azolyl An azolyl, benzothiadiazolyl, a dibenzofuranyl or a dibenzothiophenyl group; Ar 1 , Ar 2 and R′ each independently represent hydrogen, methyl, ethyl, n-propyl or isopropyl. , n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, fluorenyl, dodecyl, Hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, anthracenyl, allyldienyl, triphenyl , mercapto, fluorenyl, fused tetraphenyl, fluorenyl, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, benzimidazolyl, quinolyl, tri Base, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, pyrazolyl, fluorenyl, oxazolyl, thiazolyl, Azolyl, benzothiazolyl, benzo Azyl, morpholinyl, quin a phenyl group, or an N-carbazolyl group; each of R 1 to R 4 independently represents hydrogen, deuterium, chloro, fluoro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, Tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecanyl, trifluoromethyl, Perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, anthracenyl, biphenyl, anthracenyl, alkadienyl, a triphenyl, a fluorenyl group , fluorenyl, fused tetraphenyl, fluorenyl, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, benzimidazolyl, fluorenyl, pyridyl Base, pyrimidinyl, oxime Base, quinolyl, three Base, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, pyrazolyl, fluorenyl, oxazolyl, thiazolyl, Azolyl, benzothiazolyl, benzo Azyl, morpholinyl, N-carbazolyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethyldecyl, triethyldecyl, Tripropyldecylalkyl, tri(t-butyl)decylalkyl, tert-butyldimethylmethylalkyl, dimethylphenyldecylalkyl, or triphenylsulfonyl; each of a to d independently represents 1 or 2 The substituents of Ar 1 , Ar 2 , R′ and R 1 to R 4 may each be independently substituted by at least one group selected from the group consisting of hydrazine, chloro, fluoro, methyl, ethyl, N-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, Sulfhydryl, dodecyl, hexadecanyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, 9,9- Dimethyl fluorenyl, 9,9-diphenylfluorenyl, allyldienyl, tert-triphenyl, fluorenyl, fluorenyl, fused tetraphenyl, fluorenyl, pyridyl, pyrrolyl, furyl , thienyl, imidazolyl, benzimidazolyl, pyridyl Base, pyrimidinyl, oxime Base, quinolyl, three , benzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzothienyl, pyrazolyl, fluorenyl, oxazolyl, N-carbazolyl, thiazolyl, Azolyl, benzothiazolyl, benzo Azyl, morpholinyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethyldecyl, triethyldecyl, tripropyldecyl, Tris(t-butyl)decylalkyl, tert-butyldimethylmethylalkyl, dimethylphenyldecyl, methyldiphenyldecyl, triphenyldecyl, and N-phenylcarbazolyl . 如申請專利範圍第1項所述之化合物，其中，該式(1)表示之化合物係選自下列所組成群組： The compound according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of: 一種有機電場發光裝置，包括如申請專利範圍第1項所述之化合物。 An organic electric field illuminating device comprising the compound according to claim 1 of the patent application.
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