TW201432022A - Novel organic electroluminescent compounds and organic electroluminescent device containing the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device containing the same Download PDF

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TW201432022A
TW201432022A TW102135967A TW102135967A TW201432022A TW 201432022 A TW201432022 A TW 201432022A TW 102135967 A TW102135967 A TW 102135967A TW 102135967 A TW102135967 A TW 102135967A TW 201432022 A TW201432022 A TW 201432022A
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安熙春
梁正恩
李泰珍
朴笑美
李暻周
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 electroluminescent compound and an organic electroluminescent device containing the same. Using the organic electroluminescent compound according to the present invention, an organic electroluminescent device can have high luminescent efficiency, a long lifespan, and high current efficiency.

Description

新穎有機電場發光化合物及含該化合物之有機電場發光裝置 Novel organic electroluminescent compound and organic electric field illuminating device containing the same

本發明係關於新穎有機電場發光化合物及含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 comprising the same.

電場發光(EL)裝置係自發光裝置，其在提供更寬廣之視角、更高之對比度及更快之反應時間上具有優勢。伊士曼柯達(Eastman Kodak)首先藉由使用芳香族二胺小分子以及鋁錯合物作為形成發光層之材料研發有機EL裝置[Appl.Phys.Lett.51,913,1987]。 Electric field illuminating (EL) devices are self-illuminating devices that have advantages in providing a wider viewing angle, higher contrast, and faster reaction times. Eastman Kodak first developed an organic EL device by using an aromatic diamine small molecule and an aluminum complex as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

決定有機EL裝置中發光效率之最重要因素係發光材料。迄今為止，螢光材料業已廣泛用作為發光材料。惟，有鑑於電場發光機制，由於磷光材料理論上比螢光材料提升四(4)倍之發光效率，故磷光發光材料之研發被廣泛研究。銥(III)錯合物已廣為人知為磷光材料，包括分別作為紅色、綠色及藍色發光材料之雙(2-(2’-苯并噻吩基)-吡啶-N,C3’)銥(乙醯基丙酮)((acac)Ir(btp)2)、參(2-苯基吡啶) 銥(Ir(ppy)3)及雙(4,6-二氟苯基吡啶-N,C2)吡啶甲酸銥(Firpic)。 The most important factor determining the luminous efficiency in an organic EL device is a luminescent material. Fluorescent materials have been widely used as luminescent materials to date. However, in view of the electric field illuminating mechanism, since the phosphorescent material is theoretically improved by four (4) times the luminous efficiency of the fluorescent material, the research and development of the phosphorescent luminescent material has been extensively studied. The ruthenium (III) complex has been widely known as a phosphorescent material, including bis(2-(2'-benzothienyl)-pyridine-N,C3') oxime (acetonitrile) as red, green and blue luminescent materials, respectively. (acetone) ((acac) Ir(btp) 2 ), ginseng (2-phenylpyridine) ruthenium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridine-N,C2) pyridine formate (Firpic).

發光材料可採主體材料及摻雜劑材料之組合而使用，以改善顏色純度、發光效率及安定性。當使用主體材料/摻雜劑系統作為發光材料時，主體材料大大地影響EL裝置之效率及效能，因此，其選擇相當重要。目前，4,4’-N,N’-二咔唑-聯苯(CBP)係最廣為人知之用於磷光材料的主體材料。近來，日本先鋒公司(Pioneer)等研發了使用浴銅靈(bathocuproine,BCP)及雙(2-甲基-8-羥基喹啉)(4-苯基苯酚)鋁(III)(BAlq)等作為主體材料之高效能有機EL裝置，該等材料係作為電洞阻擋材料而為人所知。 The luminescent material can be used in combination with a host material and a dopant material to improve color purity, luminous efficiency, and stability. When a host material/dopant system is used as the luminescent material, the host material greatly affects the efficiency and performance of the EL device, and therefore, its selection is quite important. Currently, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer et al. developed the use of bathocuproine (BCP) and bis(2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq). High-performance organic EL devices for host materials, which are known as hole blocking materials.

儘管此等磷光主體材料提供良好之發光特性，他們仍具有下述缺點：(1)由於其低玻璃轉化溫度且不良熱安定性，他們可能於真空高溫沉積製程中出現降解。(2)有機EL裝置之功率效率係藉由[(Π/電壓)×電流效率]而給出，且功率效率係與電壓成反比。儘管包含磷光主體材料之有機EL裝置提供高於包含螢光材料者之電流效率(燭光(cd)/安培(A))，仍需要極高之驅動電壓。因此，於功率效率(流明(lm)/瓦(W))方面無優勢。(3)再者，該有機EL裝置之操作壽命短，且發光效率仍需改善。 Although these phosphorescent host materials provide good luminescent properties, they have the following disadvantages: (1) They may degrade in a vacuum high temperature deposition process due to their low glass transition temperature and poor thermal stability. (2) The power efficiency of the organic EL device is given by [(Π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage. Although an organic EL device including a phosphorescent host material provides higher current efficiency (candle light (cd) / amperage (A)) than those containing a fluorescent material, an extremely high driving voltage is required. Therefore, there is no advantage in terms of power efficiency (lumens (lm) / watt (W)). (3) Furthermore, the organic EL device has a short operational life and the luminous efficiency still needs to be improved.

同時，銅酞菁(CuPc)、4,4’-雙[N-(1-萘基)-N-苯基胺基]聯苯(NPB)、N,N’-二苯基-N,N’-雙(3-甲基苯基)-(1,1’-聯苯)-4,4’-二胺(TPD)、4,4’,4”-參(3-甲基苯基苯基胺基)三苯基胺(MTDATA)等係用作為電洞注入及傳輸材 料。惟，使用此等材料之有機EL裝置於量子效率及操作壽命方面存在問題。此係因為，當於高電流下驅動該有機EL裝置時，於陽極與電洞注入層之間產生熱應力。熱應力顯著降低該裝置之操作壽命。再者，由於在該電洞注入層中使用之有機材料具有非常高之電洞遷移性，可能破壞電洞-電子之電荷平衡且可能減少量子產率(cd/A)。 Meanwhile, copper phthalocyanine (CuPc), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-diphenyl-N,N '-Bis(3-methylphenyl)-(1,1'-biphenyl)-4,4'-diamine (TPD), 4,4',4"-para (3-methylphenylbenzene) Aminoamino)triphenylamine (MTDATA) is used as a hole injection and transmission material. material. However, organic EL devices using such materials have problems in terms of quantum efficiency and operational life. This is because when the organic EL device is driven at a high current, thermal stress is generated between the anode and the hole injection layer. Thermal stress significantly reduces the operational life of the device. Furthermore, since the organic material used in the hole injection layer has a very high hole mobility, the charge-electron charge balance may be destroyed and the quantum yield (cd/A) may be reduced.

韓國專利申請案公開第20110129766號揭露了用於有機EL裝置之化合物，於該等化合物中，芳基或雜芳基部份係鍵結至多環化合物之碳原子，該多環化合物係具有與雜芳基部份如苯并呋喃及苯并噻吩稠合之咔唑部份。惟，上述參考文獻未能成功地具體揭露下述化合物：於該等化合物中，含氮之雜芳基部份、連結氮之雜芳基部份(含氮或不含氮)或連結氮之芳基部份係鍵結至多環骨架之咔唑部份的氮原子。 Korean Patent Application Publication No. 20110129766 discloses a compound for use in an organic EL device in which an aryl or heteroaryl moiety is bonded to a carbon atom of a polycyclic compound having a heterocyclic The aryl moiety is a carbazole moiety fused with benzofuran and benzothiophene. However, the above references have not succeeded in specifically disclosing the following compounds: among these compounds, a nitrogen-containing heteroaryl moiety, a nitrogen-containing heteroaryl moiety (nitrogen-containing or nitrogen-free) or a nitrogen-bonded The aryl moiety is bonded to the nitrogen atom of the oxazole moiety of the polycyclic backbone.

本發明之目標係提供有機電場發光化合物，其具有比傳統材料更高之發光效率及更長之壽命，以及使用該化合物且具有高效率及長壽命之有機電場發光裝置。 The object of the present invention is to provide an organic electroluminescent compound having higher luminous efficiency and longer life than conventional materials, and an organic electric field illuminating device using the compound and having high efficiency and long life.

本發明之發明人發現可藉由下式(1)表示之化合物達成上述目的： The inventors of the present invention have found that the above object can be attained by the compound represented by the following formula (1):

其中，X表示-O-、-S-、-CR1R2-或-NR3-；L1表示經取代或未經取代之5員至30員伸雜芳基、或經取代或未經取代之(C6-C30)伸芳基；Ar1至Ar4各自獨立表示經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C6-C30)伸芳基、經取代或未經取代之5員至30員雜芳基、或經取代或未經取代之5員至30員伸雜芳基；Ar1與Ar2、Ar3與L1、或Ar3與Ar4可與於其上鍵結之氮原子連接在一起以形成含氮之5員或30員雜芳基或含氮之5員或30員伸雜芳基；表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、或經取代或未經取代之5員至30員雜芳基，或R1至R3各自獨立連接至一個或多個相鄰取代基以形成單環或多環之3員至30員脂環或芳香環；R4與R5各自獨立表示氫、氘、鹵素、氰基、羧基、硝基、羥基、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(C1-C30)烷氧基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之3員至7員雜環烷基、經取代或未經取代之(C6-C30)芳基、經取代 或未經取代之5員至30員雜芳基、-NR11R12、-SiR13R14R15、-SR16、-OR17、-COR18、或-B(OR19)(OR20)；表示氫、氘、鹵素、氰基、羧基、硝基、羥基、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(C1-C30)烷氧基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C3-C30)環烯基、經取代或未經取代之3員至7員雜環烷基、經取代或未經取代之(C6-C30)芳基、或R11至R20各自獨立經取代或未經取代之5員至30員雜芳基，或連接至一個或多個相鄰取代基以形成環中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之單環或多環之3至30員脂環或芳香環；m與n各自獨立表示1至4之整數；若m或n為2或更大之整數，則各R4或各R5可係相同或不同；以及該(伸)雜芳基含有選自B、N、O、S、P(=O)、Si及P之至少一個雜原子。 Wherein X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -; L 1 represents a substituted or unsubstituted 5 to 30 membered heteroaryl group, or substituted or unsubstituted Substituted (C6-C30) extended aryl; Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (C6-C30) extended aryl group, Substituted or unsubstituted 5 to 30 membered heteroaryl, or substituted or unsubstituted 5 to 30 membered heteroaryl; Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 Ar 4 may be bonded to the nitrogen atom to which it is bonded to form a nitrogen-containing 5 or 30 membered heteroaryl or nitrogen-containing 5 member or 30 membered heteroaryl; meaning substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted 5 to 30 membered heteroaryl, or R 1 to R 3 are each independently attached to One or more adjacent substituents to form a monocyclic or polycyclic 3- to 30-membered alicyclic or aromatic ring; R 4 and R 5 each independently represent hydrogen, deuterium, halogen, cyano, carboxy, nitro, hydroxy Substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkene , substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted Or unsubstituted 3 to 7 membered heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5 to 30 membered heteroaryl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , -COR 18 , or -B(OR 19 )(OR 20 ); represent hydrogen, hydrazine, halogen, cyano, carboxyl, nitro, hydroxy , substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or not Substituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted 3 to 7 membered heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or R 11 to R 20 each independently substituted or unsubstituted 5 to 30 membered heteroaryl, Or attached to one or more adjacent substituents to form one or more carbon atoms in the ring may be selected from at least one a 3 to 30 membered alicyclic or aromatic ring of a monocyclic or polycyclic ring in which a hetero atom of nitrogen, oxygen and sulfur is substituted; m and n each independently represent an integer of 1 to 4; if m or n is an integer of 2 or more, Then, each R 4 or each R 5 may be the same or different; and the (extended) heteroaryl group contains at least one hetero atom selected from the group consisting of B, N, O, S, P(=O), Si, and P.

根據本發明之化合物顯示高發光效率及長壽命。使用根據本發明之化合物，有機電場發光裝置展現優異之發光特性及電流效率。 The compounds according to the invention exhibit high luminous efficiency and long life. With the compound according to the present invention, the organic electric field light-emitting device exhibits excellent light-emitting characteristics and current efficiency.

後文中，將詳細揭示本發明。惟，下述說明書係意欲解釋本發明，而非意指以任何方式限制本發明之範疇。 Hereinafter, the present invention will be disclosed in detail. 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.

本發明提供上式(1)之有機電場發光化合物，包含該化合物之有機電場發光材料，以及包含該材料之有機電場發光裝置。 The present invention provides an organic electroluminescent compound of the above formula (1), an organic electroluminescent material comprising the compound, and an organic electroluminescent device comprising the material.

具體來說，本發明之式(1)之化合物係如下述者。 Specifically, the compound of the formula (1) of the present invention is as follows.

於上式(1)中，較佳地，X表示-O-、-S-、-CR1R2-或-NR3-；L1表示經取代或未經取代之(C6-C30)伸芳基；Ar1至Ar4各自獨立表示經取代或未經取代之(C6-C15)芳基、經取代或未經取代之(C6-C15)伸芳基、經取代或未經取代之5員至15員雜芳基、或經取代或未經取代之5員至15員伸雜芳基；Ar1與Ar2、Ar3與L1、或Ar3與Ar4可與鍵結其上之氮原子連接在一起以形成含氮之5員或15員雜芳基或含氮之5員或15員伸雜芳基；R1至R3各自獨立表示經取代或未經取代之(C1-C15)烷基、經取代或未經取代之(C6-C15)芳基、或經取代或未經取代之5員至15員雜芳基；R4與R5各自獨立表示氫、鹵素、經取代或未經取代之(C1-C10)烷基、經取代或未經取代之(C6-C15)芳基、經取代或未經取代之5員至15員雜芳基、或-SiR13R14R15；R13至R15各自獨立表示經取代或未經取代之(C1-C10)烷基。 In the above formula (1), preferably, X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -; and L 1 represents a substituted or unsubstituted (C6-C30) stretching. Aryl; Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C15) aryl group, a substituted or unsubstituted (C6-C15) extended aryl group, substituted or unsubstituted 5 To 15 members of heteroaryl, or substituted or unsubstituted 5 to 15 members of heteroaryl; Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 and Ar 4 may be bonded thereto The nitrogen atoms are joined together to form a nitrogen-containing 5 member or 15 membered heteroaryl group or a nitrogen-containing 5 member or a 15 membered heteroaryl group; and R 1 to R 3 each independently represent a substituted or unsubstituted group (C1) -C15) alkyl, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted 5 to 15 membered heteroaryl; R 4 and R 5 each independently represent hydrogen, halogen, Substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C15) aryl, substituted or unsubstituted 5 to 15 membered heteroaryl, or -SiR 13 R 14 R 15 ; R 13 to R 15 each independently represent a substituted or unsubstituted (C1-C10) alkyl group.

於上式(1)中，更佳地，X表示-O-、-S-、-CR1R2-或-NR3-；L1表示未經取代之(C6-C15)伸芳基；Ar1至Ar4各自獨立表 示經取代或未經取代之(C6-C15)芳基、經取代或未經取代之(C6-C15)伸芳基、經取代或未經取代之5員至15員雜芳基、或經取代或未經取代之5員至15員伸雜芳基；Ar1與Ar2、Ar3與L1、或Ar3與Ar4可與鍵結其上之氮原子連接在一起以形成含氮之5員或15員雜芳基或含氮之5員或15員伸雜芳基；R1與R2各自獨立表示經取代或未經取代之(C1-C10)烷基、或經取代或未經取代之(C6-C15)芳基；R3表示經取代或未經取代之(C6-C15)芳基；R4與R5各自獨立表示氫、未經取代之(C1-C10)烷基、或-SiR13R14R15；R13至R15各自獨立表示經取代或未經取代之(C1-C10)烷基。 In the above formula (1), more preferably, X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -; L 1 represents an unsubstituted (C6-C15) extended aryl group; Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C15) aryl group, a substituted or unsubstituted (C6-C15) extended aryl group, substituted or unsubstituted 5 to 15 a heteroaryl group, or a substituted or unsubstituted 5 to 15 member heteroaryl; Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 and Ar 4 may bond to a nitrogen atom thereon Linked together to form a nitrogen-containing 5 or 15 membered heteroaryl or nitrogen-containing 5 member or 15 membered heteroaryl; R 1 and R 2 each independently represent substituted or unsubstituted (C1-C10) An alkyl group, or a substituted or unsubstituted (C6-C15) aryl group; R 3 represents a substituted or unsubstituted (C6-C15) aryl group; and R 4 and R 5 each independently represent hydrogen, unsubstituted (C1-C10)alkyl, or -SiR 13 R 14 R 15 ; R 13 to R 15 each independently represent a substituted or unsubstituted (C1-C10) alkyl group.

本文中，「(C1-C30)烷基」表示具有1個至30個，較佳1個至10個碳原子之直鏈或分支鏈烷基，且包括甲基、乙基、正丙基、異丙基、正丁基、異丁基、第三丁基等。「(C2-C30)烯基」表示具有2個至30個，較佳2個至20個，更佳2個至10個碳原子之直鏈或分支鏈烯基，且包括乙烯基、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」表示具有2個至30個，較佳2個至20個，更佳2個至10個碳原子之直鏈或分支鏈炔基，且包括乙炔基、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」表示具有3個至30個，較佳3個至20個，更佳3個至7個碳原子之單環或多環烴，且包括環丙基、環丁基、環戊基、環己基等。「3員至7員雜環烷基」表示具有包括選自B、N、O、S、P(=O)、Si及P，較佳O、 S及N之至少一個雜原子的3個至7個環骨架原子之環烷基，且包括四氫呋喃、吡咯啶、噻喃(thiolan)、四氫吡喃等。再者，「(C6-C30)(伸)芳基」表示衍生自芳香族烴且具有6個至30個、較佳6個至15個骨架碳原子的單環或稠合環，且包括苯基、聯苯基、聯三苯基(terphenyl)、萘基、茀基、菲基、蒽基、茚基、聯伸三苯基(triphenylenyl)、芘基、稠四苯基(tetracenyl)、茈基(perylenyl)、蒯基(chrysenyl)、萘并萘基(naphthacenyl)、丙二烯合茀基(fluoranthenyl)等。「5員至30員(伸)雜芳基」表示具有包括至少一個，較佳1個至4個選自由B、N、O、S、P(=O)、Si及P所組成群組之雜原子之5個至30個，較佳5個至15個環骨架原子的芳基；其可係單環或與至少一個苯環縮合之稠合環；可係部份飽和；可係藉由將至少一個雜芳基或芳基經由一個或多個單鍵與雜芳基連接而形成者；且包括單環型雜芳基，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、異唑基、唑基、二唑基、三基、四基、三唑基、四唑基、呋呫基、吡啶基、吡基、嘧啶基、嗒基等，以及稠合環型雜芳基，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(cinnolinyl)、喹唑啉基、喹啉基、咔唑基、啡基、啡啶基、苯并二呃基(benzodioxolyl)等。再者，「鹵 素」包括F、Cl、Br及I。 Herein, "(C1-C30)alkyl" means a straight or branched alkyl group having 1 to 30, preferably 1 to 10 carbon atoms, and includes methyl, ethyl, 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, more preferably 2 to 10 carbon atoms, and includes vinyl, 1- Propylene group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methylbut-2-enyl group and the like. "(C2-C30)alkynyl" means a straight-chain or branched alkynyl group having 2 to 30, preferably 2 to 20, more preferably 2 to 10 carbon atoms, and includes ethynyl group, 1- Propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. "(C3-C30)cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, more preferably 3 to 7 carbon atoms, and includes a cyclopropyl group and a ring. Butyl, cyclopentyl, cyclohexyl and the like. "3 to 7 membered heterocycloalkyl" means having 3 to include at least one hetero atom selected from the group consisting of B, N, O, S, P(=O), Si and P, preferably O, S and N. A cycloalkyl group of 7 ring skeleton atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, and the like. Further, "(C6-C30) (extended) aryl" means a monocyclic or fused ring derived from an aromatic hydrocarbon and having 6 to 30, preferably 6 to 15 skeleton carbon atoms, and includes benzene Base, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, fluorenyl, triphenylenyl, fluorenyl, tetracenyl, fluorenyl (perylenyl), chrysenyl, naphthacenyl, fluoranthenyl, and the like. "5 to 30 members (extended) heteroaryl" means having at least one, preferably one to four, selected from the group consisting of B, N, O, S, P(=O), Si, and P. An aryl group of 5 to 30, preferably 5 to 15 ring-chain atoms of a hetero atom; which may be a single ring or a fused ring condensed with at least one benzene ring; may be partially saturated; Forming at least one heteroaryl or aryl group via a one or more single bonds to a heteroaryl group; and including a monocyclic heteroaryl group such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl , thiazolyl, thiadiazolyl, isothiazolyl, iso Azolyl, Azolyl, Diazolyl, three Base, four Base, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl Base, pyrimidinyl, oxime And the like, and fused ring-type heteroaryl such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl Benzoisothiazolyl, benzopyrene Azolyl, benzo Azyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, quinolinyl, isoquinolyl, cinnolinyl, quinazolinyl, quin Orolinyl, carbazolyl, brown Peptidyl, benzodiyl Benzodioxolyl and the like. Further, "halogen" includes F, Cl, Br, and I.

本文中，在表達方式「經取代或未經取代」中之「經取代」意指，在特定官能基之氫原子經另一種原子或基團(亦即，取代基)置換。於上式(1)中，該經取代之烷基、經取代之烯基基、經取代之炔基、經取代之烷氧基、經取代之環烷基、經取代之環烯基、經取代之雜環烷基、經取代之(伸)芳基、及經取代之(伸)雜芳基的取代基較佳各自獨立為選自下列所組成群組之至少一者：氘、鹵素、氰基、羧基、硝基、羥基、(C1-C30)烷基、鹵(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員至7員雜環烷基、(C6-C30)芳氧基、(C6-C30)芳硫基、未經取代或經(C6-C30)芳基取代之5員至30員雜芳基、未經取代或經5員至30員雜芳基取代之(C6-C30)芳基、三(C1-C30)烷基矽基、三(C6-C30)芳基矽基、二(C1-C30)烷基(C6-C30)芳基矽基、(C1-C30)烷基二(C6-C30)芳基矽基、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、(C6-C30)芳基(5員至30員)雜芳基胺基、(C1-C30)烷基羰基、(C1-C30)烷氧基羰基、(C6-C30)芳基羰基、二(C6-C30)芳基硼基(arylboronyl)、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；更佳地，選自下列所組成群組之至少一者：(C1-C6)烷基、未經取代之(C6-C30)芳基、未經取代之5員至30員雜芳基、三(C1-C30) 烷基矽基、(C6-C30)芳基(C1-C30)烷基、及(C1-C30)烷基(C6-C30)芳基；且甚至更佳地，選自下列所組成群組之至少一者：(C1-C30)烷基、未經取代之(C6-C30)芳基、(C6-C30)芳基(C1-C10)烷基、及(C1-C10)烷基(C6-C30)芳基。 As used herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom of a particular functional group is replaced by another atom or group (ie, a substituent). In the above formula (1), the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group, the substituted alkoxy group, the substituted cycloalkyl group, the substituted cycloalkenyl group, The substituted heterocycloalkyl group, the substituted (extended) aryl group, and the substituted (extended) heteroaryl group are preferably 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, unsubstituted or substituted by (C6-C30) aryl, 5 to 30 membered heteroaryl, unsubstituted or substituted with 5 to 30 membered heteroaryl (C6-C30) Aryl, tri(C1-C30)alkylindenyl, tris(C6-C30)aryldecyl, di(C1-C30)alkyl(C6-C30)arylindenyl,(C1-C30)alkyl Di(C6-C30)arylalkyl, amine, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, (C1-C30)alkyl (C6- C30) arylamine, (C6-C30) aryl (5 to 30 members) heteroarylamine (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, bis(C6-C30)arylboronyl,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 More preferably, at least one selected from the group consisting of: (C1-C6)alkyl, unsubstituted (C6-C30) aryl, unsubstituted 5 to 30 membered heteroaryl , three (C1-C30) An alkyl fluorenyl group, a (C6-C30) aryl (C1-C30) alkyl group, and a (C1-C30) alkyl (C6-C30) aryl group; and even more preferably, selected from the group consisting of At least one: (C1-C30) alkyl, unsubstituted (C6-C30) aryl, (C6-C30) aryl (C1-C10) alkyl, and (C1-C10) alkyl (C6- C30) aryl.

本發明之有機電場發光化合物包括下列者，但並不限於此： The organic electroluminescent compound of the present invention includes the following, but is not limited thereto:

本發明之化合物可藉由技術領域中具有通常知識者所習知之合成方法製備之。舉例而言，該等化合物可根據下述反應方案1製備。 The compounds of the present invention can be prepared by synthetic methods well known to those of ordinary skill in the art. For example, such compounds can be prepared according to Reaction Scheme 1 below.

再者，本發明提供包含式(1)之有機電場發光化合物的有機電場發光材料，以及包含該材料之有機電場發光裝置。該有機電場發光材料可由式(1)之有機電場發光化合物所組成。另外，該有機電場發光材料除了式(1)之有機電場發光化合物外，可復包含一種或多種傳統化合物。該有機電場發光裝置可包含第一電極、第二電極、以及至少一層位於該第一電極與第二電極間的有機層。該有機層可包含至少一種式(1)之化合物。 Furthermore, the present invention provides an organic electroluminescent material comprising an organic electroluminescent compound of the formula (1), and an organic electric field emitting device comprising the same. The organic electroluminescent material can be composed of an organic electroluminescent compound of the formula (1). Further, the organic electroluminescent material may comprise one or more conventional compounds in addition to the organic electroluminescent compound of the formula (1). The organic electric field light emitting device may include a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. The organic layer may comprise at least one compound of formula (1).

該第一電極與第二電極之一者可係陽極，且另一者可係陰極。該有機層可包含發光層，且可復包含選自電洞注入層、電洞傳輸層、電子傳輸層、電子注入層、中介層、電洞阻擋層及電子阻擋層之至少一層。 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 comprise 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, a hole barrier layer, and an electron blocking layer.

式(1)之化合物可被包含於發光層及電洞傳 輸層之至少一者中。當用於電洞傳輸層中時，式(1)之化合物可作為電洞傳輸材料而被包含。當用於發光層中時，式(1)之化合物可作為主體材料而被包含；較佳地，該發光層可復包含至少一種摻雜劑，以及，若需要，可額外包含不同於式(1)之化合物的化合物作為第二主體材料。 The compound of formula (1) can be included in the luminescent layer and the hole transmission At least one of the transport layers. When used in a hole transport layer, the compound of formula (1) can be included as a hole transport material. When used in the light-emitting layer, the compound of the formula (1) may be contained as a host material; preferably, the light-emitting layer may further comprise at least one dopant, and if necessary, may additionally comprise a different formula ( The compound of the compound of 1) is used as the second host material.

該第二主體化合物可來自任何習知磷光主體材料。具體來說，有鑑於發光效率，選自下式(2)至(4)之化合物的磷光主體材料係較佳者。 The second host compound can be from any conventional phosphorescent host material. Specifically, in view of luminous efficiency, a phosphorescent host material selected from the compounds of the following formulas (2) to (4) is preferred.

H-(Cz-L4)h-M-----------(2) H-(Cz-L 4 ) h -M-----------(2)

H-(Cz)i-L4-M-----------(3) H-(Cz) i -L 4 -M-----------(3)

其中，Cz表示下述結構： Among them, Cz represents the following structure:

R21至R24各自獨立表示氫、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5員至30員雜芳基、或R25R26R27Si-；R25至R27各自獨立表示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；L4表示單鍵、經取代或未經取代之(C6-C30)伸芳基、或經取代或未經取代之5員至30員伸雜芳基；M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5員至30員雜芳 基；Y1與Y2表示-O-、-S-、-N(R31)-、或-C(R32)(R33)-，但須滿足，Y1與Y2並不同時存在；R31至R33各自獨立表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、或經取代或未經取代之5員至30員雜芳基，且R32與R33可係相同或不同；h與i各自獨立表示1至3之整數；j、k、l及m各自獨立表示0至4之整數，且若h、i、j、k、l或m為2或更大之整數時，各(Cz-L4)、各(Cz)、各R21、各R22、各R23、或各R24可係相同或不同。 R 21 to R 24 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5 to 30 membered heteroaryl, or R 25 R 26 R 27 Si-; R 25 to R 27 each independently represent substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; L 4 represents a single bond, a substituted or unsubstituted (C6-C30) extended aryl group, or a substituted or unsubstituted 5 to 30 membered heteroaryl; M Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted 5 to 30 membered heteroaryl; Y 1 and Y 2 represent -O-, -S-, -N ( R 31 )-, or -C(R 32 )(R 33 )-, but it is satisfied that Y 1 and Y 2 are not present at the same time; R 31 to R 33 each independently represent substituted or unsubstituted (C1- C30) an alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted 5 to 30 membered heteroaryl group, and R 32 and R 33 may be the same or different; And i each independently represent an integer from 1 to 3; j, k, l and m each independently represent an integer from 0 to 4, and if h, i, j, k, l or m is 2 or The large integer, each of the (Cz-L 4), each (HCz), each of R 21, each R 22, each R 23, R 24, or each line may be the same or different.

具體言之，該第二主體材料包括下列者： Specifically, the second body material includes the following:

用於本發明之有機電場發光裝置的摻雜劑較佳係至少一種磷光摻雜劑。用於本發明之有機電場發光裝置的磷光摻雜劑並無限制，但較佳可選自銥(Ir)、鋨(Os)、銅(Cu)及鉑(Pt)之金屬化錯合化合物，更佳係選自銥(Ir)、鋨(Os)、銅(Cu)及鉑(Pt)之鄰位金屬化錯合化合物，且甚至更佳係鄰位金屬化之銥錯合化合物。 The dopant used in the organic electric field light-emitting device of the present invention is preferably at least one phosphorescent dopant. The phosphorescent dopant used in the organic electroluminescence device of the present invention is not limited, but is preferably selected from the group consisting of metal complexed compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt). More preferably, it is selected from the ortho-metallization complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metalated ruthenium complex compound.

該等磷光摻雜劑較佳可係選自下式(5)至(7)表示之化合物。 These phosphorescent dopants are preferably selected from the compounds represented by the following formulas (5) to (7).

其中，L係選自下列者： Among them, L is selected from the following:

R100表示氫、或經取代或未經取代之(C1-C30)烷基；R101至R109及R111至R123各自獨立表示氫、氘、鹵素、未經取代或經一個或多個鹵素取代之(C1-C30)烷基、氰基、或經取代或未經取代之(C1-C30)烷氧基；R120至R123可與一個或多個相鄰取代基連接以形成稠合環，如喹啉；R124至R127各自獨立表示氫、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；若R124至R127為芳基，該等可與一個或多個相鄰取代基連接以形成稠合環，如茀；R201至R211各自獨立表示氫、氘、鹵素、或未經取代或經一個或多個鹵素取代之(C1-C30)烷基；f與g各自獨立表示1至3之整數，若f或g係2或更大之整數，則各R100可係相同或不同，以及，n係1至3之整數。 R 100 represents hydrogen, or substituted or unsubstituted (C1-C30)alkyl; R 101 to R 109 and R 111 to R 123 each independently represent hydrogen, deuterium, halogen, unsubstituted or via one or more a halogen-substituted (C1-C30)alkyl group, a cyano group, or a substituted or unsubstituted (C1-C30) alkoxy group; R 120 to R 123 may be bonded to one or more adjacent substituents to form a thick a ring, such as a quinoline; R 124 to R 127 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aromatic If R 124 to R 127 are aryl, these may be bonded to one or more adjacent substituents to form a fused ring such as hydrazine; and R 201 to R 211 each independently represent hydrogen, deuterium, halogen, or un. (C1-C30)alkyl substituted or substituted with one or more halogens; f and g each independently represent an integer from 1 to 3, and if f or g is an integer of 2 or greater, each R 100 may be the same Or different, and, n is an integer from 1 to 3.

具體言之，該等磷光摻雜劑材料包括下列者： In particular, the phosphorescent dopant materials include the following:

再者，本發明提供用於製備有機電場發光裝置之材料。該材料包含本發明之有機電場發光化合物作為主體材料或電洞傳輸材料。當本發明之化合物作為主體材料而被包含時，該用於製備有機電場發光裝置之材料可復包含第二主體材料，其中，第一主體材料與第二主體材料之比可係1：99至99：1之範圍。 Further, the present invention provides a material for preparing an organic electric field light-emitting device. This material contains the organic electroluminescent compound of the present invention as a host material or a hole transporting material. When the compound of the present invention is included as a host material, the material for preparing the organic electroluminescent device may further comprise a second host material, wherein the ratio of the first host material to the second host material may be 1:99 to The range of 99:1.

此外，本發明之有機電場發光裝置包含第一電極、第二電極、以及置於該第一電極與第二電極間的至少一層有機層。該有機層包含用於製備本發明之有機電場發光裝置的材料。 Further, the organic electric field light-emitting device of the present invention comprises 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 a material for preparing the organic electric field illuminating device of the present invention.

本發明之有機電場發光裝置的有幾層除了包含式(1)之化合物外，可復包含至少一種選自芳基胺系化 合物及苯乙烯基芳基胺系化合物所組成群組的化合物。 The organic electroluminescent device of the present invention may have several layers in addition to the compound of the formula (1), and may further comprise at least one selected from the group consisting of arylamines. A compound of the group consisting of a compound and a styryl arylamine compound.

於本發明之有機電場發光裝置中，該有機層除了包含式(1)之化合物外，可復包含至少一種選自週期表第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、鑭系元素、及d-過渡元素之有機金屬所組成群組之金屬，或包含該金屬的至少一種錯合化合物。該有機層可包含發光層及電荷產生層。 In the organic electric field light-emitting device of the present invention, the organic layer may comprise at least one metal selected from the group 1 of the periodic table, the metal of the second group, and the transition metal of the fourth cycle, in addition to the compound of the formula (1). a metal of the group consisting of transition metals of the fifth cycle, lanthanides, and organometallics of the d-transition element, or at least one compound of the compound comprising the metal. The organic layer may include a light emitting layer and a charge generating layer.

此外，本發明之有機電場發光裝置可藉由復包含至少一層發光層而發白光，該發光層除了包含本發明之化合物外，亦包含該領域中習知之藍色電場發光化合物、紅色電場發光化合物或綠色電場發光化合物。又，若需要，該裝置中可包含黃色或橘色發光層。 In addition, the organic electroluminescent device of the present invention can emit white light by further comprising at least one luminescent layer. In addition to the compound of the present invention, the luminescent layer also includes a blue electric field luminescent compound and a red electric field luminescent compound which are well known in the art. Or a green electric field luminescent compound. Also, if desired, the device may comprise a yellow or orange luminescent layer.

根據本發明，可將至少一層選自硫屬元素化合物層、金屬鹵化物層及金屬氧化物層的層(後文中稱為「表面層」)置於一個或兩個電極之一個或多個內表面上。詳言之，較佳係將矽或鋁之硫屬元素化合物(包括氧化物)層置於電場發光介質層之陽極表面上，並將金屬鹵化物層或金屬氧化物層置於電場發光介質層之陰極表面上。此表面層對該有機電場發光裝置提供操作安定性。較佳地，該硫屬元素化合物包括SiOX(1X2)、AlOX(1X1.5)、SiON、SiAlON等；該金屬鹵化物包括LiF、MgF2、CaF2、稀土金屬氟化物等；且該金屬氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。 According to the present invention, at least one layer selected from the group consisting of a chalcogen compound layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") may be placed in one or more of one or two electrodes. On the surface. In particular, it is preferred to place 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 place the metal halide layer or the metal oxide layer on the electric field luminescent medium layer. On the surface of the cathode. This surface layer provides operational stability to the organic electric field illuminating device. Preferably, the chalcogen compound comprises SiO X (1 X 2), AlO X (1 X 1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF 2 , CaF 2 , rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, and the like.

於本發明之有機電場發光裝置中，可將電 子傳輸化合物與還原性摻雜劑之混合區域或電洞傳輸化合物與氧化性摻雜劑之混合區域置於成對電極之至少一表面上。於此情況，該電子傳輸化合物還原為陰離子，因此其變得更容易自該混合區域注射並傳輸電子至電場發光介質。再者，該電洞傳輸化合物氧化為陽離子，因此其變得更容易自該混合區域注射並傳輸電洞至該電場發光介質。較佳地，該氧化性摻雜劑包括多種路易士酸(Lewis acid)以及受體(acceptor)化合物；以及，該還原性摻雜劑包括鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬、及其混合物。還原性摻雜劑層可用作為電荷產生層以製備具有兩層或更多層電場發光層並發白光(或稱白色)之電場發光裝置。 In the organic electric field light-emitting device of the present invention, electricity can be used A mixed region of the sub-transport compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant is placed on at least one surface of the pair of electrodes. In this case, the electron transporting compound is reduced to an anion, so that it becomes easier to inject and transport electrons from the mixed region to the electric field illuminating medium. Furthermore, the hole transport compound is oxidized to a cation, so that it becomes easier to inject and transport holes from the mixed region to the electric field illuminating medium. Preferably, the oxidizing dopant comprises a plurality of Lewis acid and an acceptor compound; and the reducing dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, a rare earth metal, and Its mixture. A reducing dopant layer can be used as the charge generating layer to prepare an electric field illuminating device having two or more layers of an electroluminescent layer and emitting white light (or white).

為了形成本發明之有機電場發光裝置之各層，可使用乾式薄膜形成法(例如：真空蒸發、濺鍍、電漿法及離子鍍覆方法)，或濕式薄膜形成法(例如：旋塗、浸塗、及流動塗佈方法)。 In order to form the layers of the organic electroluminescent device of the present invention, dry film formation methods (for example, vacuum evaporation, sputtering, plasma plating, and ion plating methods) or wet film formation methods (for example, spin coating, dipping) may be used. Coating, and flow coating methods).

後文中，將參照下列實施例詳細解釋該化合物、該化合物之製備方法、以及該裝置的發光特性。 Hereinafter, the compound, the preparation method of the compound, and the luminescent properties of the device will be explained in detail with reference to the following examples.

[實施例] [Examples] 實施例1：化合物C-2之製備 Example 1: Preparation of Compound C-2

化合物1-1之製備 Preparation of Compound 1-1

將蒸餾水(H2O)(200毫升(mL))加入2-溴硝基苯(30公克(g),148毫莫耳(mmol))、4-二苯并噻吩硼酸(41g,178mmol)、肆(三苯基膦)鈀(0)[Pd(PPh3)4](6.5g,5.9mmol)、Na2CO3(39g,370mmol)、甲苯(600ml)及乙醇(EtOH)(200mL)之混合物中後，將該混合物於120℃攪拌2小時。反應完成後，以蒸餾水洗滌該混合物，以乙酸乙酯(EA)萃取，以MgSO4乾燥有機層。隨後，以旋轉蒸發器移除溶劑，將剩餘產物以管柱色層分析法純化以獲得化合物1-1(39g,86%)。 Distilled water (H 2 O) (200 mL (mL)) was added to 2-bromonitrobenzene (30 g (g), 148 mmol (mmol)), 4-dibenzothiophene boronic acid (41 g, 178 mmol),肆(triphenylphosphine)palladium(0)[Pd(PPh 3 ) 4 ](6.5g, 5.9mmol), Na 2 CO 3 (39g, 370mmol), toluene (600ml) and ethanol (EtOH) (200mL) After the mixture, the mixture was stirred at 120 ° C for 2 hours. After completion of the reaction, the mixture was distilled organic layer was dried over MgSO 4 and washed with ethyl acetate (EA) extracted. Subsequently, the solvent was removed with a rotary evaporator, and the residue was purified by column chromatography to yield Compound 1-1 (39 g, 86%).

化合物1-2之製備 Preparation of Compound 1-2

於150℃，於圓底燒瓶(RBF)中，將2-(二苯并噻吩-4-基)-硝基苯(39g,128mmol)、亞磷酸三乙酯[P(OEt)3](300mL)及1,2-二氯苯(300mL)之混合物攪拌8小時。藉由在真空下蒸餾移除溶劑後，以管柱色層分析法純化所得之粗產物以獲得化合物1-2(21g,61%)。 2-(Dibenzothiophen-4-yl)-nitrobenzene (39 g, 128 mmol), triethyl phosphite [P(OEt) 3 ] (300 mL) at 150 ° C in a round bottom flask (RBF) A mixture of 1,2-dichlorobenzene (300 mL) was stirred for 8 hours. After removing the solvent by distillation under vacuum, the obtained crude product was purified by column chromatography to afford compound 1-2 (21 g, 61%).

化合物2-1之製備 Preparation of Compound 2-1

將H2O(90mL)加入4-溴-2-氟硝基苯(15g,68mmol)、苯基硼酸(9.1g,75mmol)、Pd(PPh3)4(3.5g,4.6mmol)、Na2CO3(18g,170mmol)、甲苯(270mL)及EtOH(90mL)之混合物中後，將該混合物於120℃迴流下攪拌2小時。反應完成之後，以蒸餾水洗滌該混合物，以EA萃取，以MgSO4乾燥有機層。隨後，使用旋轉蒸發器移除溶劑，以管柱色層分析法純化剩餘產物以獲得化合物2-1(9.2g,62%)。 Add H 2 O (90 mL) to 4-bromo-2-fluoronitrobenzene (15 g, 68 mmol), phenylboronic acid (9.1 g, 75 mmol), Pd(PPh 3 ) 4 (3.5 g, 4.6 mmol), Na 2 After a mixture of CO 3 (18 g, 170 mmol), toluene (270 mL) and EtOH (90 mL), the mixture was stirred at 120 ° C for 2 hr. After completion of the reaction, the mixture was distilled organic layer was dried over MgSO 4 washed, extracted with EA. Subsequently, the solvent was removed using a rotary evaporator, and the remaining product was purified by column chromatography to give Compound 2-1 (9.2 g, 62%).

化合物2-2之製備 Preparation of Compound 2-2

將5H-[1]苯并噻吩并[3,2-c]咔唑(8.8g,40.5mmol)溶解於二甲基甲醯胺(DMF)(180mL)中後，將NaH(1.9g,60%礦物油溶液，48.6mmol)緩慢加入該溶液中。攪拌15分鐘後，將溶解於DMF(20mL)中之4-氟-2-苯基硝基苯(8.8g,40.5mmol)緩慢逐滴加入該溶液中。將該反應溶液於室溫攪拌4小時，隨後藉由加入甲醇淬滅之。以EA/H2O處理該所得物之後，以管柱色層分析法純化粗產物以獲得化合物2-2(19g,100%)。 After 5H-[1]benzothieno[3,2-c]carbazole (8.8 g, 40.5 mmol) was dissolved in dimethylformamide (DMF) (180 mL), NaH (1.9 g, 60) % mineral oil solution, 48.6 mmol) was slowly added to the solution. After stirring for 15 minutes, 4-fluoro-2-phenylnitrobenzene (8.8 g, 40.5 mmol) dissolved in DMF (20 mL) was slowly added dropwise to the solution. The reaction solution was stirred at room temperature for 4 hours and then quenched by the addition of methanol. After the resultant was treated with EA/H 2 O, the crude product was purified by column chromatography to afford compound 2-2 (19 g, 100%).

化合物2-3之製備 Preparation of Compound 2-3

於150℃，於RBF中，將2-苯基-4-(苯并噻吩并[3,2-c]咔唑基)-硝基苯(19g,40.3mmol)、P(OEt)3(80mL)及1,2-二氯苯(120mL)之混合物攪拌8小時。藉由在真空下蒸餾移除溶劑之後，以管柱色層分析法純化所得粗產物以獲得化合物2-3(12g,68%)。 2-Phenyl-4-(benzothieno[3,2-c]oxazolyl)-nitrobenzene (19 g, 40.3 mmol), P(OEt) 3 (80 mL) in RBF at 150 °C A mixture of 1,2-dichlorobenzene (120 mL) was stirred for 8 hours. After removing the solvent by distillation under vacuum, the obtained crude product was purified by column chromatography to afford compound 2-3 (12 g, 68%).

化合物C-2之製備 Preparation of Compound C-2

將3-(苯并噻吩并[3,2-c]咔唑基)-咔唑(10g,22.8mmol)、9-苯基-3-溴咔唑(8g,25mmol)、CuI(2g,11.4mmol)、乙二胺(1.5mL,22.8mmol)、磷酸鉀(12g,57mmol)及甲苯(200mL)之混合物於RBF中迴流8小時。冷卻至室溫後，過濾該反應混合物，以二氯甲烷(MC)洗滌。於減壓下蒸餾濾液，以管柱色層分析法純化以獲得化合物C-2(11g,71%)。 3-(Benzothieno[3,2-c]oxazolyl)-oxazole (10 g, 22.8 mmol), 9-phenyl-3-bromocarbazole (8 g, 25 mmol), CuI (2 g, 11.4) A mixture of mmol), ethylenediamine (1.5 mL, 22.8 mmol), potassium phosphate (12 g, 57 mmol) and toluene (200 mL) was refluxed for 8 hours in RBF. After cooling to room temperature, the reaction mixture was filtered and washed with dichloromethane (EtOAc). The filtrate was distilled under reduced pressure and purified by column chromatography to yield Compound C-2 (11 g, 71%).

UV=308nm，PL=383nm，mp=241℃。MS/EIMS計算值為679.21，實測值為679.83。 UV = 308 nm, PL = 383 nm, mp = 241 °C. MS/EIMS calculated 679.21, found 679.83.

實施例2：化合物C-6之製備 Example 2: Preparation of Compound C-6

以與實施例1之化合物2-3相同之方式製備化合物2-4。於120℃，將化合物2-3(5.9g,14mmol)、3-溴-N,N-二苯基苯胺(5g,15mmol)、CuI(1.3g,6.9mmol)、K3PO4(8.9g,42mmol)、乙二胺(1.9mL,28mmol)及甲苯(70mL)之混合物於250mL RBF中攪拌過夜。以EA/H2O處理該反應混合物之後，以MgSO4乾燥，並於減壓下蒸餾。以使用MC/己烷(Hx)之管柱色層分析法純化粗產物以獲得化合物C-6(白色固體，6.9g,74%)。 Compound 2-4 was prepared in the same manner as Compound 2-3 of Example 1. Compound 2-3 (5.9 g, 14 mmol), 3-bromo-N,N-diphenylaniline (5 g, 15 mmol), CuI (1.3 g, 6.9 mmol), K 3 PO 4 (8.9 g) A mixture of ethylenediamine (1.9 mL, 28 mmol) and toluene (70 mL) was stirred in 250 mL of RBF overnight. After the reaction mixture was treated with EA / H 2 O, dried over MgSO 4 and evaporated. The crude product was purified by column chromatography using EtOAc / EtOAc (EtOAc)

UV=314nm，PL=381nm，mp=236℃，MS/EIMS計算值為665.25；實測值為665.78。 UV = 314 nm, PL = 381 nm, mp = 236 ° C, MS/EIMS calculated 665.25; found 665.78.

實施例3：化合物C-62之製備 Example 3: Preparation of Compound C-62

化合物5-1之製備 Preparation of Compound 5-1

於120℃，將二苯基胺(20g,118mmol)、4-溴-4’-碘苯基 (63.6g,177mmol)、參(二亞苄基丙酮)二鈀(0)[Pd2(dba)3](3.2g,3.5mmol)、三(鄰甲苯基)膦[P(o-tol)3](2.9g,9.4mmol)、第三丁醇鈉(NaOtBu)(22.7g,236mmol)及甲苯(1000mL)之混合物於2L大小之RBF中攪拌1小時。以EA/H2O處理該反應混合物之後，以MgSO4乾燥，並於減壓下蒸餾。以使用MC：Hx之管柱色層分析法純化粗產物以獲得化合物5-1(13.4g,28%)。 Diphenylamine (20 g, 118 mmol), 4-bromo-4'-iodophenyl (63.6 g, 177 mmol), gin (dibenzylideneacetone) dipalladium (0) [Pd 2 (dba) at 120 °C 3 ] (3.2 g, 3.5 mmol), tris(o-tolyl)phosphine [P(o-tol) 3 ] (2.9 g, 9.4 mmol), sodium butoxide (NaO t Bu) (22.7 g, 236 mmol) A mixture of toluene (1000 mL) was stirred in 2 L of RBF for 1 hour. After the reaction mixture was treated with EA / H 2 O, dried over MgSO 4 and evaporated. The crude product was purified by column chromatography chromatography using MC:Hx to afford compound 5-1 (13.4 g, 28%).

化合物C-62之製備 Preparation of Compound C-62

於120℃，將化合物2-4(6.3g,15mmol)、化合物5-1(6.6g,16.5mmol)、CuI(1.4g,7.5mmol)、K3PO4(9.5g,45mmol)、乙二胺(2mL,30mmol)及甲苯(75mL)於250Ml大小之RBF中攪拌8小時。以EA/H2O處理該反應混合物，以MgSO4乾燥，並於減壓下蒸餾。以使用MC：Hx之管柱色層分析法純化粗產物以獲得化合物C-62(白色固體，7.6g,68%)。 Compound 2-4 (6.3 g, 15 mmol), compound 5-1 (6.6 g, 16.5 mmol), CuI (1.4 g, 7.5 mmol), K 3 PO 4 (9.5 g, 45 mmol), Ethylene at 120 ° C Amine (2 mL, 30 mmol) and toluene (75 mL) were stirred in <RTIgt; In EA / H 2 O The reaction mixture was treated, dried MgSO 4, and distilled under reduced pressure. The crude product was purified by column chromatography using EtOAc: EtOAc (EtOAc)

UV=344nm，PL=397nm，mp=173℃。MS/EIMS計算值為741.28；實測值為741.88。 UV = 344 nm, PL = 397 nm, mp = 173 °C. MS/EIMS calculated 741.28; found 741.88.

實施例4：化合物C-71之製備 Example 4: Preparation of Compound C-71

化合物3-1之製備 Preparation of Compound 3-1

將化合物1-2(20g,73mmol)、3-溴碘苯(41g,146mmol)、CuI(7g,36.5mmol)、乙二胺(9mL,146mmol)、碳酸銫(45g,146mmol)及甲苯(400mL)之混合物於RBF中迴流3小時。將該反應混合物冷卻至室溫。隨後，過濾並以MC洗滌。濾液於減壓下蒸餾，並以管柱色層分析法純化以獲得化合物3-1(23g,54%)。 Compound 1-2 (20 g, 73 mmol), 3-bromoiodobenzene (41 g, 146 mmol), CuI (7 g, 36.5 mmol), ethylenediamine (9 mL, 146 mmol), cesium carbonate (45 g, 146 mmol) and toluene (400 mL) The mixture was refluxed for 3 hours in RBF. The reaction mixture was cooled to room temperature. Subsequently, it was filtered and washed with MC. The filtrate was distilled under reduced pressure and purified by column chromatography to yield Compound 3-1 (23 g, 54%).

化合物4-2之製備 Preparation of Compound 4-2

將化合物4-1(25g,77mmol)、苯胺(14g,154mmol)、醋酸鈀(II)[Pd(OAc)2](0.35g,1.54mmol)、三-第三丁基膦[P(tBu)3](3mL,7.7mmol)、碳酸銫(50g,154mmol)及二甲苯(400mL)之混合物於RBF中迴流8小時。將該反應混合物冷卻至室溫。隨後，過濾並以MC洗滌。濾液於減壓下蒸餾，並以管柱色層分析法純化以獲得化合物4-2(20g,77%)。 Compound 4-1 (25 g, 77 mmol), aniline (14 g, 154 mmol), palladium (II) acetate [Pd(OAc) 2 ] (0.35 g, 1.54 mmol), tri-tert-butylphosphine [P(tBu) A mixture of 3 ] (3 mL, 7.7 mmol), cesium carbonate (50 g, 154 mmol) and xylene (400 mL) was refluxed in RBF for 8 hours. The reaction mixture was cooled to room temperature. Subsequently, it was filtered and washed with MC. The filtrate was distilled under reduced pressure and purified by column chromatography to afford compound 4-2 (20 g, 77%).

化合物C-71之製備 Preparation of Compound C-71

將化合物3-1(10g,23.3mmol)、化合物4-2(7.9g,23.3mmol)、Pd2(dba)3(0.43g,0.47mmol)、P(tBu)3(1mL,2.4mmol)、第三丁醇鈉(3.5g,35mmol)及二甲苯(120mL)之混合物於RBF中迴流8小時。將該反應混合物冷卻至室溫。隨後，過濾並以MC洗滌。濾液於減壓下蒸餾，並以管柱色層分析法純化以獲得化合物C-71(10.2g,64%)。 Compound 3-1 (10 g, 23.3 mmol), compound 4-2 (7.9 g, 23.3 mmol), Pd 2 (dba) 3 (0.43 g, 0.47 mmol), P(tBu) 3 (1 mL, 2.4 mmol), A mixture of sodium butoxide (3.5 g, 35 mmol) and xylene (120 mL) was refluxed in RBF for 8 h. The reaction mixture was cooled to room temperature. Subsequently, it was filtered and washed with MC. The filtrate was distilled under reduced pressure and purified by column chromatography to yield Compound C-71 (10.2 g, 64%).

UV=310nm，PL=383nm，mp=205℃。MS/EIMS計算值為683.24；實測值為683.86。 UV = 310 nm, PL = 383 nm, mp = 205 °C. MS/EIMS calculated 683.24; found 683.86.

裝置實施例1：使用本發明之化合物之 OLED裝置 Apparatus Example 1: Use of the compound of the present invention OLED device

使用根據本發明之材料製造OLED裝置。使用超音波依序以三氯乙烯、丙酮、乙醇及蒸餾水洗滌有機發光二極體(OLED)裝置用玻璃基板(Samsung Corning，大韓民國)上之透明電極氧化銦錫(ITO)薄膜(15Ω/sq)，隨後儲存於異丙醇中。隨後，將該ITO基板裝配於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一小室(cell)中，隨後控制該裝置之壓力為10-6托耳(torr)。之後，將電流施加至該小室以蒸發上述導入之材料，從而於該ITO基板上形成厚度為60nm之電洞注入層。隨後，將有機電場發光化合物C-2導入該真空氣相沉積裝置之另一小室中，藉由將電流施加至該小室而使之蒸發，從而於該電洞注入層上形成厚度為20nm之電洞傳輸層。之後，將5-(4-([1,1’：4’,1”-聯三苯]-3-基)嘧啶-2-基)-5H-苯并[4,5]噻吩并[3,2-c]咔唑導入該真空氣相沉積裝置之一小室中作為主體材料，將化合物D-1導入另一小室中作為摻雜劑。以不同速率蒸發兩種材料，並以該主體材料與摻雜劑之總量為基準，以15wt%的摻雜量沉積，以於該電洞傳輸層上形成厚度為30nm之發光層。隨後，將2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑導入一小室中，並將8-羥基喹啉鋰(lithium quinolate,Liq)導入另一小室中。以相同速率蒸發該兩種材料並分別以50wt%之摻雜量沉積，以於該發光層上形成厚度為30nm之電子傳輸層。隨 後，於該電子傳輸層上沉積厚度為2nm之8-羥基喹啉鋰作為電子注入層之後，藉由另一真空氣相沉積裝置於該電子注入層上沉積厚度為150nm之鋁(Al)陰極。因而，製得OLED裝置。所有用於製造該OLED裝置之材料係於使用前藉由在10-6托真空昇華而予以純化。所製得之OLED裝置顯示具有亮度為5350燭光(cd)/平方公尺(m2)且電流密度為13.1毫安培(mA)/平方公分(cm2)之綠光。 An OLED device is fabricated using the material according to the invention. Transparent electrode indium tin oxide (ITO) film (15 Ω/sq) on a glass substrate for organic light-emitting diode (OLED) devices (Samsung Corning, Republic of Korea) was washed with ultrasonic waves using trichloroethylene, acetone, ethanol and distilled water. And then stored in isopropanol. Subsequently, 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 one of the cells of the vacuum vapor deposition apparatus, and then the pressure of the apparatus is controlled to be 10 -6 torr. Thereafter, a current was applied to the cell to evaporate the introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Subsequently, the organic electroluminescent compound C-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and is evaporated by applying a current to the chamber to form a thickness of 20 nm on the hole injection layer. Hole transport layer. Thereafter, 5-(4-([1,1':4',1"-bitriphenyl]-3-yl)pyrimidin-2-yl)-5H-benzo[4,5]thieno[3] , 2-c] oxazole is introduced into a chamber of the vacuum vapor deposition apparatus as a host material, and compound D-1 is introduced into another chamber as a dopant. The two materials are evaporated at different rates and the host material is used. On the basis of the total amount of the dopant, it is 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. Subsequently, 2-(4-(9,10-two) Naphthalen-2-yl)indol-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole is introduced into a small chamber, and lithium quinolate (Liq) is introduced into another In a small chamber, the two materials are evaporated at the same rate and deposited at a doping amount of 50 wt%, respectively, to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Subsequently, a thickness of 2 nm is deposited on the electron transport layer. After lithium 8-hydroxyquinolate is used as an electron injecting layer, an aluminum (Al) cathode having a thickness of 150 nm is deposited on the electron injecting layer by another vacuum vapor deposition apparatus. Thus, an OLED device is produced. The material of the OLED device is borrowed before use. 10-6 Torr and be purified by vacuum sublimation. The OLED device prepared with a display luminance of 5350 candles (cd) / square meter (m 2) and a current density of 13.1 milliamperes (mA) / square centimeter (cm 2 ) the green light.

裝置實施例2：使用本發明之有機電場發光化合物之OLED裝置 Device Example 2: OLED device using the organic electroluminescent compound of the present invention

以與裝置實施例1之相同方式製造OLED裝置，除了使用化合物C-71以形成厚度為20nm之電洞傳輸層，且於該真空氣相沉積裝置之一小室中作為主體材料之9-(4-([1,1’：3’,1”-聯三苯]-4-基)嘧啶-2-基)-3-(二苯并[b,d]噻吩-4-基)-9H-咔唑與另一小室中作為摻雜劑之化合物D-25兩者以不同速率蒸發，且以該主體及摻雜劑之總量為基準計，15wt%之摻雜量沉積，以於該電洞傳輸層上形成厚度為30nm之發光層。所製得之OLED裝置顯示具有亮度為11000cd/m2且電流密度為24.1mA/cm2之綠光。 The OLED device was fabricated in the same manner as in Device Example 1, except that the compound C-71 was used to form a hole transport layer having a thickness of 20 nm, and 9-(4) as a host material in one of the chambers of the vacuum vapor deposition device. -([1,1':3',1"-bitriphenyl]-4-yl)pyrimidin-2-yl)-3-(dibenzo[b,d]thiophen-4-yl)-9H- The carbazole and the compound D-25 as a dopant in another chamber are evaporated at different rates, and 15 wt% of the doping amount is deposited based on the total amount of the host and the dopant, so that the electricity A light-emitting layer having a thickness of 30 nm was formed on the hole transport layer. The obtained OLED device showed green light having a luminance of 11,000 cd/m 2 and a current density of 24.1 mA/cm 2 .

裝置實施例3：使用本發明之有機電場發光化合物之OLED裝置 Device Example 3: OLED device using the organic electroluminescent compound of the present invention

以與裝置實施例1之相同方式製造OLED裝置，除了使用化合物C-6以形成厚度為20nm之電洞傳輸層，且於該真空氣相沉積裝置之一小室中作為主體材料之9-(4-([1,1’-聯苯]-4-基)喹唑啉-2-基)-9’-苯基-9H,9’H-3,3’-聯咔 唑與另一小室中作為摻雜劑之化合物D-78兩者以不同速率蒸發，且以該主體及摻雜劑之總量為基準計，3wt%之摻雜量沉積，以於該電洞傳輸層上形成厚度為30nm之發光層。所製得之OLED裝置顯示具有亮度為7000cd/m2且電流密度為50.4mA/cm2之紅光。 An OLED device was fabricated in the same manner as in Device Example 1, except that Compound C-6 was used to form a hole transport layer having a thickness of 20 nm, and 9-(4) as a host material in one of the chambers of the vacuum vapor deposition apparatus. -([1,1'-biphenyl]-4-yl)quinazolin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole with another chamber The compound D-78 as a dopant is evaporated at different rates, and a doping amount of 3 wt% is deposited on the basis of the total amount of the host and the dopant to form a thickness on the hole transport layer. 30 nm luminescent layer. The prepared OLED device showed red light having a luminance of 7000 cd/m 2 and a current density of 50.4 mA/cm 2 .

裝置實施例4：使用本發明之有機電場發光化合物之OLED裝置 Device Example 4: OLED device using the organic electroluminescent compound of the present invention

以與裝置實施例1之相同方式製造OLED裝置，除了使用化合物C-62以形成厚度為20nm之電洞傳輸層。所製得之OLED裝置顯示具有亮度為3000cd/m2且電流密度為7.1mA/cm2之綠光。 The OLED device was fabricated in the same manner as in Device Example 1, except that the compound C-62 was used to form a hole transport layer having a thickness of 20 nm. The prepared OLED device showed green light having a luminance of 3000 cd/m 2 and a current density of 7.1 mA/cm 2 .

比較裝置實施例1：使用傳統材料之OLED裝置 Comparison device Example 1: OLED device using conventional materials

以與裝置實施例1之相同方式製造OLED裝置，除了使用N,N’-二(4-聯苯)-N,N’-二(4-聯苯)-4,4’-二胺基聯苯以形成厚度為20nm之電洞傳輸層；使用4,4’-N,N’-二咔唑-聯苯作為主體材料且使用Ir(ppy)3(D-15)作為摻雜劑於該電洞傳輸層上形成厚度為30nm之發光層；且使用雙(2-甲基-8-羥基喹啉)-4-苯基苯酚鋁(III)以形成厚度為10nm之電洞阻擋層。所製得之OLED裝置顯示具有亮度為2750cd/m2且電流密度為8.30mA/cm2之綠光。 An OLED device was fabricated in the same manner as in Device Example 1, except that N,N'-bis(4-biphenyl)-N,N'-bis(4-biphenyl)-4,4'-diamine linkage was used. Benzene to form a hole transport layer having a thickness of 20 nm; using 4,4'-N,N'-dicarbazole-biphenyl as a host material and using Ir(ppy) 3 (D-15) as a dopant A light-emitting layer having a thickness of 30 nm was formed on the hole transport layer; and bis(2-methyl-8-hydroxyquinoline)-4-phenylphenol aluminum (III) was used to form a hole barrier layer having a thickness of 10 nm. The prepared OLED device showed green light having a luminance of 2750 cd/m 2 and a current density of 8.30 mA/cm 2 .

比較裝置實施例2：使用傳統材料之OLED裝置 Comparison device embodiment 2: OLED device using conventional materials

以與裝置實施例1之相同方式製造OLED裝置，除了 使用N,N’-二(4-聯苯)-N,N’-二(4-聯苯)-4,4’-二胺基聯苯以形成厚度為20nm之電洞傳輸層；使用CBP作為主體材料且使用D-80作為摻雜劑於該電洞傳輸層上形成厚度為30nm之發光層；且使用雙(2-甲基-8-羥基喹啉)-4-苯基苯酚鋁(III)以形成厚度為10nm之電洞阻擋層。所製得之OLED裝置顯示具有亮度為1700cd/m2且電流密度為32.1mA/cm2之紅光。 An OLED device was fabricated in the same manner as in Device Example 1, except that N,N'-bis(4-biphenyl)-N,N'-bis(4-biphenyl)-4,4'-diamine linkage was used. Benzene to form a hole transport layer having a thickness of 20 nm; forming a light-emitting layer having a thickness of 30 nm on the hole transport layer using CBP as a host material and using D-80 as a dopant; and using bis(2-methyl-) 8-Hydroxyquinolinate-4-phenylphenol aluminum (III) to form a hole barrier layer having a thickness of 10 nm. The prepared OLED device showed red light having a luminance of 1700 cd/m 2 and a current density of 32.1 mA/cm 2 .

如上所述，本發明之有機電場發光化合物具有優於傳統材料之特性，故，使用本發明之有機電場發光化合物的裝置展現傑出之發光特性及電流效率。 As described above, the organic electroluminescent compound of the present invention has characteristics superior to those of conventional materials, and therefore, the apparatus using the organic electroluminescent compound of the present invention exhibits excellent luminescent characteristics and current efficiency.

Claims (6)

一種下式(1)表示之有機電場發光化合物， 其中，X表示-O-、-S-、-CR1R2-或-NR3-；L1表示經取代或未經取代之5員至30員伸雜芳基、或經取代或未經取代之(C6-C30)伸芳基；Ar1至Ar4各自獨立表示經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C6-C30)伸芳基、經取代或未經取代之5員至30員雜芳基、或經取代或未經取代之5員至30員伸雜芳基；Ar1與Ar2、Ar3與L1、或Ar3與Ar4可與鍵結其上之氮原子連接在一起以形成含氮之5員或30員雜芳基或含氮之5員或30員伸雜芳基；表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、或經取代或未經取代之5員至30員雜芳基，或R1至R3各自獨立與一個或多個相鄰取代基連接以形成單環或多環之3員至30員脂環或芳香環；R4與R5各自獨立表示氫、氘、鹵素、氰基、羧基、硝基、羥基、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(C1-C30)烷氧基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之3員至7員雜環烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之5員至30員雜芳基、-NR11R12、-SiR13R14R15、-SR16、-OR17、-COR18、或-B(OR19)(OR20)；表示氫、氘、鹵素、氰基、羧基、硝基、羥基、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(C1-C30)烷氧基、經取代或未經取代之(C3-C30)環烷基、經取代或未經取代之(C3-C30)環烯基、經取代或未經取代之3員至7員雜環烷基、經取代或未經取代之(C6-C30)芳基、或經取代或未經取代之5員至30員雜芳基，或R11至R20各自獨立連接至一個或多個相鄰取代基以形成環中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之單環或多環之3至30員脂環或芳香環；m與n各自獨立表示1至4之整數；若m或n為2或更大之整數，則各R4或各R5可係相同或不同；以及該(伸)雜芳基含有至少一個選自B、N、O、S、P(=O)、Si及P之雜原子。 An organic electric field luminescent compound represented by the following formula (1), Wherein X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -; L 1 represents a substituted or unsubstituted 5 to 30 membered heteroaryl group, or substituted or unsubstituted Substituted (C6-C30) extended aryl; Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (C6-C30) extended aryl group, Substituted or unsubstituted 5 to 30 membered heteroaryl, or substituted or unsubstituted 5 to 30 membered heteroaryl; Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 Ar 4 may be bonded to a nitrogen atom bonded thereto to form a nitrogen-containing 5 member or 30 membered heteroaryl group or a nitrogen-containing 5 member or 30 membered heteroaryl group; meaning substituted or unsubstituted ( a C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted 5 to 30 membered heteroaryl group, or R 1 to R 3 each independently and one or a plurality of adjacent substituents are joined to form a monocyclic or polycyclic 3 to 30 member alicyclic or aromatic ring; R 4 and R 5 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, Substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl Substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or substituted Unsubstituted 3- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 5 to 30 membered heteroaryl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , -COR 18 , or -B(OR 19 )(OR 20 ); represent hydrogen, hydrazine, halogen, cyano, carboxyl, nitro, hydroxy, Substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted Substituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted 3 to 7 membered heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted 5 to 30 membered heteroaryl, or R 11 to R 20 are each independently Attaching to one or more adjacent substituents to form one or more carbon atoms in the ring may be at least one selected from the group consisting of nitrogen a monocyclic or polycyclic 3 to 30 membered alicyclic or aromatic ring of a hetero atom or a heterocyclic ring of oxygen; m and n each independently represent an integer of 1 to 4; and if m or n is an integer of 2 or more, Each R 4 or each R 5 may be the same or different; and the (extended) heteroaryl group contains at least one hetero atom selected from the group consisting of B, N, O, S, P(=O), Si, and P. 如申請專利範圍第1項所述之有機電場發光化合物，其中，X表示-O-、-S-、-CR1R2-或-NR3-；L1表示經取代或未經取代之(C6-C30)伸芳基； Ar1至Ar4各自獨立表示經取代或未經取代之(C6-C15)芳基、經取代或未經取代之(C6-C15)伸芳基、經取代或未經取代之5員至15員雜芳基、或經取代或未經取代之5員至15員伸雜芳基；Ar1與Ar2、Ar3與L1、或Ar3與Ar4可與鍵結其上之氮原子連接在一起以形成含氮之5員或15員雜芳基或含氮之5員或15員伸雜芳基；R1至R3各自獨立表示經取代或未經取代之(C1-C15)烷基、經取代或未經取代之(C6-C15)芳基、或經取代或未經取代之5員至15員雜芳基；R4與R5各自獨立表示氫、鹵素、經取代或未經取代之(C1-C10)烷基、經取代或未經取代之(C6-C15)芳基、經取代或未經取代之5員至15員雜芳基、或-SiR13R14R15；R13至R15各自獨立表示經取代或未經取代之(C1-C10)烷基。 The organic electroluminescent compound according to claim 1, wherein X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -; and L 1 represents substituted or unsubstituted ( C6-C30) an aryl group; Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C15) aryl group, a substituted or unsubstituted (C6-C15) extended aryl group, substituted or Unsubstituted 5 to 15 membered heteroaryl, or substituted or unsubstituted 5 to 15 membered heteroaryl; Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 and Ar 4 may Attached to the nitrogen atom bonded to the nitrogen atom to form a nitrogen-containing 5 member or 15 member heteroaryl group or a nitrogen-containing 5 member or 15 member heteroaryl group; R 1 to R 3 each independently represent substituted or unsubstituted Substituted (C1-C15) alkyl, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted 5 to 15 membered heteroaryl; R 4 and R 5 are each independently Represents hydrogen, halogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C15) aryl, substituted or unsubstituted 5 to 15 membered heteroaryl Or -SiR 13 R 14 R 15 ; R 13 to R 15 each independently represent substituted or unsubstituted (C1-C10)alkyl. 如申請專利範圍第1項所述之有機電場發光化合物，其中，X表示-O-、-S-、-CR1R2-或-NR3-；L1表示未經取代之(C6-C15)伸芳基；Ar1至Ar4各自獨立表示經取代或未經取代之(C6-C15)芳基、經取代或未經取代之(C6-C15)伸芳基、經取代或未經取代之5員至15員雜芳基、或經取代或未經取代之5員至15員伸雜芳基；Ar1與Ar2、Ar3與L1、或Ar3與Ar4可與鍵結其上之 氮原子連接在一起以形成含氮之5員或15員雜芳基或含氮之5員或15員伸雜芳基；R1與R2各自獨立表示經取代或未經取代之(C1-C10)烷基、或經取代或未經取代之(C6-C15)芳基；R3表示經取代或未經取代之(C6-C15)芳基；R4與R5各自獨立表示氫、未經取代之(C1-C10)烷基、或-SiR13R14R15；R13至R15各自獨立表示經取代或未經取代之(C1-C10)烷基。 The organic electroluminescent compound according to claim 1, wherein X represents -O-, -S-, -CR 1 R 2 - or -NR 3 -; and L 1 represents unsubstituted (C6-C15) Arylene; Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C15) aryl group, a substituted or unsubstituted (C6-C15) extended aryl group, substituted or unsubstituted 5 to 15 membered heteroaryl, or substituted or unsubstituted 5 to 15 membered heteroaryl; Ar 1 and Ar 2 , Ar 3 and L 1 , or Ar 3 and Ar 4 may be bonded The nitrogen atoms thereon are joined together to form a nitrogen-containing 5 or 15 membered heteroaryl or a nitrogen-containing 5 member or a 15 membered heteroaryl group; R 1 and R 2 each independently represent substituted or unsubstituted (C1-C10)alkyl, or substituted or unsubstituted (C6-C15) aryl; R 3 represents substituted or unsubstituted (C6-C15) aryl; R 4 and R 5 are each independently represented Hydrogen, unsubstituted (C1-C10)alkyl, or -SiR 13 R 14 R 15 ; R 13 to R 15 each independently represent a substituted or unsubstituted (C1-C10)alkyl group. 如申請專利範圍第1項所述之有機電場發光化合物，其中，於L1、Ar1至Ar4、R1至R5、及R11至R20中，該經取代之烷基、經取代之烯基、經取代之炔基、經取代之烷氧基、經取代之環烷基、經取代之環烯基、經取代之雜環烷基、經取代之(伸)芳基、經取代之(伸)雜芳基的取代基各自獨立為選自下列所組成之群組的至少一者：氘、鹵素、氰基、羧基、硝基、羥基、(C1-C30)烷基、鹵(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員至7員雜環烷基、(C6-C30)芳氧基、(C6-C30)芳硫基、未經取代或經(C6-C30)芳基取代之5員至30員雜芳基、未經取代或經5員至30員雜芳基取代之(C6-C30)芳基、三(C1-C30)烷基矽基、三(C6-C30)芳基矽基、二(C1-C30)烷基(C6-C30)芳基矽基、(C1-C30)烷基二(C6-C30)芳基矽基、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、(C6-C30)芳基(5員至30員)雜芳基胺基、(C1-C30)烷基羰基、(C1-C30)烷氧基羰基、(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 the substituted alkyl group is substituted in L 1 , Ar 1 to Ar 4 , R 1 to R 5 , and R 11 to R 20 Alkenyl, substituted alkynyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted (extended) aryl, substituted The substituents of the (hetero)heteroaryl group are each independently at least one selected from the group consisting of hydrazine, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halogen ( 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, unsubstituted or substituted by (C6-C30) aryl 5 to 30 membered heteroaryl, unsubstituted or substituted by 5 to 30 membered heteroaryl (C6-C30) aryl, tri(C1-C30)alkyl fluorenyl, tris(C6-C30) Aryl fluorenyl, bis(C1-C30)alkyl (C6-C30) aryl fluorenyl, (C1-C30)alkyl bis(C6-C30) aryl fluorenyl, amine, mono or di (C1- C30) alkylamine group, single Or a di(C6-C30)arylamino group, a (C1-C30)alkyl (C6-C30) arylamino group, a (C6-C30) aryl group (5 to 30 members) heteroarylamine group, C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboryl, di(C1-C30)alkylboryl, C1-C30) alkyl (C6-C30) aryl boron group, (C6-C30) aryl (C1-C30) alkyl group, and (C1-C30) alkyl (C6-C30) aryl group. 如申請專利範圍第1項所述之有機電場發光化合物，其中，式(1)表示之該化合物係選自下列所組成之群組： The organic electroluminescent 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，係包含如申請專利範圍第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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Publication number Priority date Publication date Assignee Title
CN108922975A (en) * 2018-06-26 2018-11-30 长春海谱润斯科技有限公司 A kind of organic electroluminescent device

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