TWI461509B - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

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

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TWI461509B
TWI461509B TW099120052A TW99120052A TWI461509B TW I461509 B TWI461509 B TW I461509B TW 099120052 A TW099120052 A TW 099120052A TW 99120052 A TW99120052 A TW 99120052A TW I461509 B TWI461509 B TW I461509B
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Taiwan
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substituted
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aryl
alkyl
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TW099120052A
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TW201114880A (en
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Chi Sik Kim
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Dow Advanced Display Material Ltd
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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

本發明係關於一種新穎有機電場發光化合物及包含該化合物之有機電場發光裝置。根據本發明之有機電場發光化合物係如化學式(1)所示：The present invention relates to a novel organic electroluminescent compound and an organic electric field illuminating device comprising the same. The organic electroluminescent compound according to the present invention is as shown in the chemical formula (1):

在眾多顯示裝置之中，電場發光裝置(electroluminescent,EL)作為自體發光裝置的優點在於它們提供了寬廣的視角、優越的對比與高回應速率。1987年時，Eastman Kodak首先開發出一種有機EL裝置，其係使用低分子量芳香族二胺與鋁錯化物作為形成電場發光層之物質[App1 .Phys .Lett . 51,913,1987]。Among many display devices, the advantage of electroluminescent (EL) as a self-illuminating device is that they provide a wide viewing angle, superior contrast and high response rate. In 1987, Eastman Kodak first developed an organic EL device using low molecular weight aromatic diamines and aluminum complexes as materials for forming an electroluminescent layer [App1 .Phys .Lett . 51, 913, 1987].

在有機EL裝置中，當施加電荷至有機層(形成於電子注入電極(陰極)與電洞注入電極(陽極)之間)時，電子與電洞會配成對，並在電子-電洞對消耗後發射出光。有機EL裝置的優點在於：其可形成於撓性透明基材上(例如塑膠)；相較於電漿顯示器面板或無機EL顯示器，其用相對低的電壓(10或更低)即可操作；消耗較低的功率；以及提供優質的顏色。此外，因能呈現綠、藍及紅色，有機EL裝置受矚目成為下一代、全色彩顯示裝置。In an organic EL device, when charges are applied to an organic layer (formed between an electron injecting electrode (cathode) and a hole injecting electrode (anode)), electrons and holes are paired and in an electron-hole pair After the consumption, the light is emitted. An advantage of the organic EL device is that it can be formed on a flexible transparent substrate (for example, plastic); it can be operated with a relatively low voltage (10 or lower) compared to a plasma display panel or an inorganic EL display; Consumes lower power; and provides superior color. In addition, organic EL devices have attracted attention as next-generation, full-color display devices because of their ability to display green, blue, and red.

在有機EL裝置中，決定其效能(包括發光效率與操作壽命)的最重要因素為電場發光材料。電場發光材料的一些要件包括於固態之高電場發光量子產率(quantum yield)、高電子及電洞遷移率、真空沉積期間的高分解抗性、形成均勻薄膜的能力以及穩定性。In an organic EL device, the most important factor determining its performance, including luminous efficiency and operational lifetime, is an electric field luminescent material. Some of the requirements for electroluminescent materials include solid state high electric field luminescence quantum yield, high electron and hole mobility, high decomposition resistance during vacuum deposition, ability to form a uniform film, and stability.

一般而言，有機EL裝置通常具有陽極/電洞注入層(HIL)/電洞傳輸層(HTL)/發光材料層(EML)/電子傳輸層(ETL)/電子注入層(EIL)/陰極之組構。有機電場發光裝置發射藍、綠或紅光者，其可依據如何形成發光材料層而製造。In general, organic EL devices generally have an anode/hole injection layer (HIL)/hole transport layer (HTL)/luminescent material layer (EML)/electron transport layer (ETL)/electron injection layer (EIL)/cathode Fabrication. The organic electric field illuminating device emits blue, green or red light, which can be manufactured depending on how the luminescent material layer is formed.

在功能性方面，電場發光材料可切分為主體材料與摻雜劑材料。一般而言，已知電場發光層藉由摻雜摻雜劑於主體中而製造者能提供優越的EL特性。近來，開發具高效率與長操作壽命之有機EL正成為迫在眉急的要務。尤其是，考慮到中至大尺寸(OLED)面板需要之EL效能程度，開發明顯優於現存電場發光材料之材料有迫切的需求。In terms of functionality, the electroluminescent material can be divided into a host material and a dopant material. In general, it is known that an electroluminescent layer can provide superior EL characteristics by doping a dopant into a host. Recently, the development of organic EL with high efficiency and long operating life is becoming an urgent task. In particular, there is an urgent need to develop materials that are significantly superior to existing electroluminescent materials in view of the degree of EL performance required for medium to large size (OLED) panels.

就藍光電場發光材料而言，許多材料已接著Idemitsu Kosan的DPVBi之後商品化了。除了Idemitsu Kosan的藍光材料系統以外，Kodak的二萘基蒽(dinaphthylanthracene)及四(第三丁基)苝(tetra(t-butyl)perylene)已為眾知，但仍需要進一步的研究與開發。迄今為止，已知Idemitsu Kosan的二苯乙烯化合物具有最佳的發光效率。其呈現6流明/瓦(lm/w)的功率以及30,000小時或更長的操作壽命。然而，其天空藍(sky-blue)顏色並不適合於全彩色顯示器。一般而言，如果電場發光波長稍往較長波長偏移，藍光電場發光在發光效率方面就變得有利。但是，如此並不適用於高品質顯示器，因為無法達到純藍的顏色。因此，改善色純度(color purity)、效率以及熱穩定性的研究及開發有著高度的需求。As far as the blue electric field luminescent material is concerned, many materials have been commercialized after the DPVBi of Idemitsu Kosan. In addition to the blue light material system of Idemitsu Kosan, Kodak's dinaphthylanthracene and tetra(t-butyl)perylene are well known, but further research and development are still needed. To date, Idemitsu Kosan's stilbene compound has been known to have an optimum luminous efficiency. It exhibits 6 lumens per watt (lm/w) of power and an operational life of 30,000 hours or more. However, its sky-blue color is not suitable for full color displays. In general, if the electric field emission wavelength is slightly shifted by a longer wavelength, the blue electric field illumination becomes advantageous in terms of luminous efficiency. However, this does not apply to high-quality displays because pure blue colors cannot be achieved. Therefore, there is a high demand for research and development to improve color purity, efficiency, and thermal stability.

為了提供具高效率與長壽命的主體材料，已有各種具不同骨幹結構的EL化合物被揭露，包括二螺-茀-蒽(dispiro-fluorene-anthracene)(TBSA)、三-螺茀(ter-spirofluorene)(TSF)、雙聯伸三苯(bitriphenylene)(BTP)等。然而，它們都無法在色純度或發光效率方面提供令人滿意的結果。In order to provide a host material having high efficiency and long life, various EL compounds having different backbone structures have been disclosed, including dispiro-fluorene-anthracene (TBSA) and tri-spiro (ter- Spirofluorene) (TSF), bitriphenylene (BTP), and the like. However, none of them can provide satisfactory results in terms of color purity or luminous efficiency.

TBSA係由Gyeongsang University及Samsung SDI[Kwon,S. K. et al.,Advanced Materials,2001,13,1690；日本專利早期公開案JP 2002121547]所發表者，其於7.7伏特(V)下表現出3燭光/安培(cd/A)之發光效率，以及相對較好的色坐標(color corrdinate)(0.15,0.11)，但是其為單層之材料，且不適合商業用途。TBSA is published by Gyeongsang University and Samsung SDI [Kwon, SK et al., Advanced Materials, 2001, 13, 1690; Japanese Patent Laid-Open Publication No. JP 2002121547], which exhibits 3 candelas at 7.7 volts (V) / The luminescence efficiency of ampere (cd/A), and relatively good color corrdinate (0.15, 0.11), but it is a single layer of material and is not suitable for commercial use.

TSF係由國立臺灣大學(Wu,C. C. et al.,Advanced Materials,2004,16,61；美國專利公開案US 2005040392)所發表者，其表現出相對較好的外部量子效率(5.3%)，但對實際應用仍不足。此外，BTP係由國立臺灣清華大學(Cheng,C. -H. et al.,Advanced Materials,2002,14,1409；美國專利公開案第US 2004076852號)所發表者，其表現出2.76 cd/A的發光效率以及相對較好的色坐標(0.16,0.14)，但對實際應用仍然不足。如上所述，現存的單層材料未使用主體-摻雜劑薄膜層，就色純度及效率來說，被認為難以達到商業化。再者，它們缺乏關於操作壽命方面的可靠數據。TSF is published by National Taiwan University (Wu, CC et al., Advanced Materials, 2004, 16, 61; US Patent Publication US 2005040392), which exhibits relatively good external quantum efficiency (5.3%), but The actual application is still insufficient. In addition, the BTP is published by the National Taiwan Tsinghua University (Cheng, C.-H. et al., Advanced Materials, 2002, 14, 1409; US Patent Publication No. US 2004076852), which exhibits 2.76 cd/A. The luminous efficiency and relatively good color coordinates (0.16, 0.14), but still not enough for practical applications. As described above, the existing single-layer material does not use a host-dopant film layer, and it is considered to be difficult to commercialize in terms of color purity and efficiency. Furthermore, they lack reliable data on operational life.

根據Mitsui Chemical之專利(美國專利公開案第7,166,240號)，下列所示之化合物具有390至430奈米(nm)之吸收光譜，並表現出4.6 cd/A的發光效率。然而，因具有上述吸收波長，藍綠色(bluish green color)之發光為可預期的。實際上，該專利所陳述的是藍綠色。因所揭露的是對稱結構，所以不可能獲得純藍色。此等材料無法發射純藍顏色，並不適用於全彩色顯示器。According to the patent of Mitsui Chemical (U.S. Patent No. 7,166,240), the compound shown below has an absorption spectrum of 390 to 430 nanometers (nm) and exhibits a luminous efficiency of 4.6 cd/A. However, due to the above absorption wavelength, the luminescence of bluish green color is expected. In fact, the patent states that it is blue-green. Because of the symmetrical structure revealed, it is impossible to obtain pure blue. These materials do not emit pure blue colors and are not suitable for full color displays.

關於綠色螢光材料，參(8-羥基喹啉)鋁(III)(Alq)用來當主體，而將香豆素衍生物(coumarin derivative)(C545T)、喹吖酮衍生物(quinacridone derivative)、DPT等用來當摻雜劑，摻雜濃度為百分之幾至幾十。雖然現存電場發光材料表現出可商業化之初始發光效率，此效率卻隨時間快速衰減。因為壽命問題，它們難以應用於高效能、大尺寸面板。Regarding the green fluorescent material, ginseng (8-hydroxyquinoline) aluminum (III) (Alq) is used as a host, and a coumarin derivative (C545T), a quinacridone derivative. DPT or the like is used as a dopant, and the doping concentration is several to several tens of percent. While existing electric field luminescent materials exhibit commercially viable initial luminous efficiencies, this efficiency decays rapidly over time. They are difficult to apply to high-performance, large-sized panels because of life issues.

因此，有必要開發能提供OLED裝置滿意的操作壽命、較佳穩定性以及優質的效能之主體材料。Therefore, it is necessary to develop a host material that can provide a satisfactory operational life, better stability, and superior performance of an OLED device.

技術難題technical challenge

因此，本發明之一目的在於提供有一種機電場發光化合物，其具有優於現存材料之發光效率及裝置操作壽命，且具備帶有適當的色坐標之較佳骨幹及以解決先前問題。本發明之另一目的在於提供一種有機電場發光裝置，其使用該有機電場發光化合物作為有機電場發光材料。Accordingly, it is an object of the present invention to provide an electro-optic luminescent compound having superior luminous efficacy and device operational life over existing materials, and having a preferred backbone with appropriate color coordinates to solve the previous problems. Another object of the present invention is to provide an organic electric field light-emitting device using the organic electroluminescent compound as an organic electroluminescent material.

技術方案Technical solutions

在一通常態樣中，本發明提供化學式(1)所示之有機電場發光化合物，以及含此化合物之有機電場發光裝置。因具有較佳的發光效率及優良的壽命特性，本發明之有機電場發光化合物可用於製造具有極優操作壽命之OLED裝置。In a general aspect, the present invention provides an organic electroluminescent compound of the formula (1), and an organic electric field light-emitting device comprising the same. The organic electroluminescent compound of the present invention can be used to manufacture an OLED device having an excellent operational life because of its excellent luminous efficiency and excellent life characteristics.

其中，R1 至R18 獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、與一個或多個經取代或未經取代之(C3-C30)環烷基稠合之經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C3-C30)雜芳基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基、與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基、氰基、NR21 R22 、BR23 R24 、PR25 R26 、P(=O)R27 R28 [其中，R21 至R28 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C3-C30)雜芳基]、Ra Rb Rc Si-[其中，Ra 、Rb 、Rc 獨立地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]、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、Rd Y-[其中，Y表示S或O，且Rd 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]、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、Re C(=O)-[其中，Re 表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C6-C30)芳氧基]、Rf C(=O)O-[其中，Rf 表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C6-C30)芳氧基]、羧基、硝基、或羥基，或者，它們可藉由具有或不具有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或多環之芳環；A、B以及W獨立地表示-(CR51 R52 )m -、-(R51 )C=C(R52 )-、-N(R53 )-、-S-、-O-、-Si(R54 )(R55 )-、-P(R56 )-、-P(=O)(R57 )-、-C(=O)-或-B(R58 )-，其中，R51 至R58 及R61 至R63 與R1 至R18 相同；該雜環烷基及雜芳基可含一個或多個選自B、N、O、S、P(=O)、Si及P之雜原子；以及m表示1或2之整數。Wherein R 1 to R 18 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, and one or more Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted 5 to 7 membered heterocycloalkyl group, a 5 to 7 membered heterocycloalkyl group fused to one or more substituted or unsubstituted aromatic rings, substituted or unsubstituted ( C3-C30) cycloalkyl, (C3-C30)cycloalkyl fused to one or more substituted or unsubstituted aromatic rings, cyano, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P(=O)R 27 R 28 [wherein, R 21 to R 28 independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group. Or a substituted or unsubstituted (C3-C30)heteroaryl], R a R b R c Si-[wherein, R a , R b , R c independently represent substituted or unsubstituted ( C1-C30)alkyl, or substituted or unsubstituted (C6-C30) aryl], substituted or unsubstituted (C6-C30) aryl (C1- C30) alkyl, R d Y- [wherein Y represents S or O, and R d represents a substituted or unsubstituted (C1-C30) alkyl group or a substituted or unsubstituted (C6-C30) aryl group. (C2-C30)alkenyl, substituted or unsubstituted (C2-C30)alkynyl, R e C(=O)-[wherein R e represents substituted or Unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C6-C30) aryloxy], R f C(=O)O-[wherein, R f represents a substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C1 -C30) alkoxy, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C6-C30) aryloxy], carboxyl, nitro, Or a hydroxy group, or they may be bonded to an adjacent substituent by a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form an alicyclic ring, or a monocyclic ring or Polycyclic aromatic rings; A, B and W independently represent -(CR 51 R 52 ) m -, -(R 51 )C=C(R 52 )-, -N(R 53 )-, -S-, -O-, -Si(R 54 )(R 55 )-, -P(R 56 )-, -P(=O)(R 57 )-, -C(=O)- or -B(R 58 ) Wherein R 51 to R 58 and R 61 to R 63 are the same as R 1 to R 18 ; the heterocycloalkyl and heteroaryl group may contain one or more selected from the group consisting of B, N, O, S, P ( =O), heteroatoms of Si and P; and m represents an integer of 1 or 2.

在本發明中，“烷基”、“烷氧基”及其他含“烷基”部份(moiety)之取代基包括直鏈與分支鏈種類兩者，而且“環烷基”包括單環烴以及多環烴(例如經取代或未經取代之金剛烷基或經取代或未經取代之(C7-C30)雙環烷基)。在本發明中，“芳基”表示經由除去一個氫原子而自芳香族烴衍生的有機基，而且可包括含有4至7元，較佳為5或6元單環或稠合環，包括數個藉由單鍵鍵聯之芳基。芳基的具體實例包括苯基、萘基、聯苯基、蒽基、茚基、茀基、菲基、聯伸三苯基(triphenylenyl)、芘基、苝基(perylenyl)、蒯基(chrysenyl)、稠四苯基(naphthacenyl)、丙二烯合茀基(fluoranthenyl)等，但不限於此。該萘基包含1-萘基及2-萘基，該蒽基包含1-蒽基、2-蒽基及9-蒽基，且該茀基包含1-茀基、2-茀基、3-茀基、4-茀基及9-茀基。In the present invention, "alkyl", "alkoxy" and other substituents containing "alkyl" moieties include both straight-chain and branched-chain species, and "cycloalkyl" includes monocyclic hydrocarbons. And polycyclic hydrocarbons such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl. In the present invention, "aryl" means an organic group derived from an aromatic hydrocarbon by removing one hydrogen atom, and may include a 4- or 7-membered, preferably 5 or 6-membered monocyclic or fused ring, including An aryl group linked by a single bond. Specific examples of the aryl group include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, a fluorenyl group, a fluorenyl group, a phenanthryl group, a triphenylenyl group, a fluorenyl group, a perylenyl group, and a chrysenyl group. , but not limited to, naphthacenyl, fluoranthenyl, and the like. The naphthyl group includes a 1-naphthyl group and a 2-naphthyl group, and the fluorenyl group includes a 1-fluorenyl group, a 2-fluorenyl group, and a 9-fluorenyl group, and the fluorenyl group includes a 1-fluorenyl group, a 2-fluorenyl group, and 3- Sulfhydryl, 4-mercapto and 9-fluorenyl.

在本發明中，術語“雜芳基”表示含有1至4個選自B、N、O、S、P(=O)、Si及P之雜原子作為芳香族環狀骨幹原子，及碳原子作為其他剩餘的芳香族環狀骨幹原子之芳基。其可為5或6元單環雜芳基或由與苯環縮合而成的多環雜芳基，而且可為部分飽合。再者，此雜芳基包括多於一個藉由單鍵鍵結的雜芳基。雜芳基可包含二價芳基，其中，環中的雜原子可經氧化或四級化(quaternize)而形成，例如，N-氧化物或四級鹽。雜芳基的具體實例包括單環雜芳基，例如，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；以及多環之雜芳基，例如，苯并呋喃基、苯并噻吩基、異苯并呋喃基、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(quinazolinyl)、喹啉基、咔唑基、啡啶基、苯并二苊基(benzodioxolyl)等、其N-氧化物(例如，吡啶基N-氧化物，喹啉基N-氧化物)、其四級鹽類等，但不限於此。In the present invention, the term "heteroaryl" means a hetero atom containing from 1 to 4 selected from the group consisting of B, N, O, S, P(=O), Si and P as an aromatic cyclic backbone atom, and a carbon atom. As an aryl group of other remaining aromatic cyclic backbone atoms. It may be a 5 or 6 membered monocyclic heteroaryl group or a polycyclic heteroaryl group formed by condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl group includes more than one heteroaryl group bonded by a single bond. The heteroaryl group may comprise a divalent aryl group, wherein the hetero atom in the ring may be formed by oxidation or quaternization, for example, an N-oxide or a quaternary salt. Specific examples of the heteroaryl group include a monocyclic heteroaryl group, for example, a furyl group, a thienyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, a thiadiazolyl group, an isothiazolyl group, and a different Azolyl, Azolyl, Diazolyl, three Base, four Base, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl Base, pyrimidinyl, oxime And other heteroaryl groups, for example, benzofuranyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benziso Azolyl, benzo Azyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, quinolyl, isoquinolinyl, cinnolinyl, quinazolinyl, quin Orolinyl, oxazolyl, phenanthryl, benzodiazepine A benzodioxolyl or the like, an N-oxide thereof (for example, a pyridyl N-oxide, a quinolinyl N-oxide), a quaternary salt thereof, or the like, but is not limited thereto.

在本發明中，“(C1-C30)烷基”包括(C1-C20)烷基或(C1-C10)烷基，且“(C6-C30)芳基”包括(C6-C20)芳基或(C6-C12)芳基。“(C3-C30)雜芳基”包括(C3-C20)雜芳基或(C3-C12)雜芳基，以及“(C3-C30)環烷基”包括(C3-C20)環烷基或(C3-C7)環烷基。“(C2-C30)烯基或炔基”包括(C2-C20)烯基或炔基，或(C2-C10)烯基或炔基。In the present invention, "(C1-C30)alkyl" includes (C1-C20)alkyl or (C1-C10)alkyl, and "(C6-C30)aryl" includes (C6-C20)aryl or (C6-C12) aryl. "(C3-C30)heteroaryl" includes (C3-C20)heteroaryl or (C3-C12)heteroaryl, and "(C3-C30)cycloalkyl" includes (C3-C20)cycloalkyl or (C3-C7) cycloalkyl. "(C2-C30)alkenyl or alkynyl" includes (C2-C20)alkenyl or alkynyl, or (C2-C10)alkenyl or alkynyl.

而且，在本發明中，術語“經取代或未經取代”或“具有或不具有取代基”表示取代基可經一個或多個選自下列所組成群組之取代基取代：氫、氘、鹵素、具有或不具鹵素取代基之(C1-C30)烷基、(C6-C30)芳基、具有或不具(C6-C30)芳基取代基之(C3-C30)雜芳基、5至7元雜環烷基、與一個或多個芳環稠合之5至7元雜環烷基、(C3-C30)環烷基、與一個或多個芳環稠合之(C3-C30)環烷基、三(C1-C30)烷基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、三(C6-C30)芳基矽烷基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、NR31 R32 、BR33 R34 、PR35 R36 、P(=O)R37 R38 [其中，R31 至R38 獨立地表示(C1-C30)烷基、(C6-C30)芳基或(C3-C30)雜芳基]、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、(C1-C30)烷氧基、(C1-C30)烷基硫基、(C6-C30)芳氧基、(C6-C30)芳硫基、(C1-C30)烷氧基羰基、(C1-C30)烷基羰基、(C6-C30)芳基羰基、(C6-C30)芳氧基羰基、(C1-C30)烷氧基羰氧基、(C1-C30)烷基羰氧基、(C6-C30)芳基羰氧基、(C6-C30)芳氧基羰氧基、羧基、硝基以及羥基；或者，可鍵聯至相鄰取代基以形成環。Moreover, in the present invention, the term "substituted or unsubstituted" or "with or without a substituent" means that the substituent may be substituted with one or more substituents selected from the group consisting of hydrogen, hydrazine, Halogen, (C1-C30)alkyl with or without a halogen substituent, (C6-C30) aryl, (C3-C30)heteroaryl with or without (C6-C30) aryl substituent, 5 to 7 a heterocycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings, a (C3-C30)cycloalkyl group, a (C3-C30) ring fused to one or more aromatic rings Alkyl, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl,tri(C6-C30)aryldecyl,(C2-C30)alkenyl (C2-C30)alkynyl, cyano, oxazolyl, NR 31 R 32 , BR 33 R 34 , PR 35 R 36 , P(=O)R 37 R 38 [wherein R 31 to R 38 independently Represents (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl], (C6-C30)aryl(C1-C30)alkyl, (C1-C30)alkyl ( C6-C30) aryl, (C1-C30) alkoxy, (C1-C30)alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkane Oxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30) arylcarbonyl (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) An aryloxycarbonyloxy group, a carboxyl group, a nitro group, and a hydroxyl group; or, may be bonded to an adjacent substituent to form a ring.

R1 至R18 、R21 至R28 、R51 至R58 及R61 至R63 獨立地選自氫、氘、鹵素，烷基(例如甲基、乙基、丙基、丁基、戊基、己基、乙基己基、庚基、辛基等)、芳基(例如苯基、萘基、茀基、聯苯基、菲基、聯三苯基(terphenyl)、芘基、苝基、螺雙茀基(spirobifluorenyl)、丙二烯合茀基、蒯基、聯伸三苯基等)、與一個或多個環烷基稠合之芳基(例如1,2-二氫苊基(1,2-dihydroacenaphthyl)等)、雜芳基(例如二苯并噻吩基(dibenzothiophenyl)、二苯并呋喃基(dibenzofuranyl)、咔唑基(carbazolyl)、吡啶、呋喃、噻吩基(thienyl)、喹啉基(quinolyl)、三基(triazinyl)、嘧啶基(pyrimidinyl)、嗒基(pyridazinyl)、喹啉基(quinoxalinyl)、啡啉基(phenanthrolinyl)等)、與一個或多個芳環稠合之雜環烷基(例如N-苯并吡咯啶基(benzopyrrolidino)、N-苯并哌啶基(benzopiperidino)、N-二苯并嗎啉基(dibenzomorpholino)、N-二苯并氮呯基(dibenzoazepino)等)、經芳基(例如苯基、萘基、茀基、聯苯基、菲基、聯三苯基(terphenyl)、芘基、苝基、螺雙茀基、丙二烯合茀基、蒯基、聯伸三苯基等)取代之胺基、經雜芳基(例如二苯并噻吩基、二苯并呋喃基、咔唑基、吡啶、呋喃、噻吩基、喹啉基、三基、嘧啶基、嗒基、喹啉基、啡啉基等)取代之胺基、芳氧基(例如聯苯基氧基(biphenyloxy)等)、芳硫基(聯苯基硫基(biphenylthio)等)、芳烷基(例如聯苯甲基、三苯基甲基等)、以及，但不限於此。它們可進一步如化學式1所定義般經取代。R 1 to R 18 , R 21 to R 28 , R 51 to R 58 and R 61 to R 63 are independently selected from hydrogen, hydrazine, halogen, alkyl (for example, methyl, ethyl, propyl, butyl, pentyl) Base, hexyl, ethylhexyl, heptyl, octyl, etc.), aryl (eg phenyl, naphthyl, anthracenyl, biphenyl, phenanthryl, terphenyl, fluorenyl, fluorenyl, An aryl group fused to one or more cycloalkyl groups (for example, 1,2-dihydroindenyl (1), spirobifluorenyl, propadienyl, fluorenyl, triphenyl, etc. , 2-dihydroacenaphthyl), etc., heteroaryl (such as dibenzothiophenyl, dibenzofuranyl, carbazolyl, pyridine, furan, thienyl, quinoline Quinolyl, three Triazinyl, pyrimidinyl, anthraquinone Pyridazinyl, quinine a quinoxalinyl, phenanthrolinyl, etc., heterocycloalkyl fused to one or more aromatic rings (eg, N-benzopyrrolidino, N-benzopiperidinyl ( Benzopiperidino), N-dibenzomorpholino, dibenzoazepino, etc., aryl (eg phenyl, naphthyl, anthryl, biphenyl, phenanthryl, An amine group substituted with a terphenyl group, a fluorenyl group, a fluorenyl group, a spirobiguanyl group, a propadienyl fluorenyl group, a fluorenyl group, a co-triphenyl group, or the like, and a heteroaryl group (for example, dibenzothiophene) Base, dibenzofuranyl, carbazolyl, pyridine, furan, thienyl, quinolyl, tri Base, pyrimidinyl, oxime Base Alkyl group, aryloxy group (e.g., biphenyloxy group, etc.), arylthio group (biphenylthio, etc.), aralkyl group (e.g., phenyl group, phenanthyl group, etc.) Benzyl, triphenylmethyl, etc.), as well as , but not limited to this. They can be further substituted as defined in Chemical Formula 1.

根據本發明之有機電場發光化合物可以下列化合物例示之，但不限於此：The organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but is not limited thereto:

根據本發明之有機電場發光化合物可由流程圖1製備，但不限於此。The organic electroluminescent compound according to the present invention can be prepared by the scheme 1, but is not limited thereto.

其中R1 至R18 、A及B與化學式1中的定義相同。Wherein R 1 to R 18 , A and B are the same as defined in Chemical Formula 1.

在另一通常態樣中，本發明提供一種有機電場發光裝置，包括：第一電極；第二電極；以及一層或多層有機層，係設於第一電極以及第二電極之間，其中，有機層包括一個或多個化學式(1)所示之有機電場發光化合物。此有機電場發光化合物係用來作為電場發光層中的主體材料。In another general aspect, the present invention provides an organic electric field light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein The layer includes one or more organic electroluminescent compounds of the formula (1). This organic electroluminescent compound is used as a host material in an electroluminescent layer.

有機層可包括電場發光層，該場發光層除了包含一個或多個化學式(1)所示的有機電場發光化合物以外，還包含一個或多個摻雜劑。本發明之有機電場發光裝置中使用的摻雜劑並無特別限制。The organic layer may include an electric field luminescent layer containing one or more dopants in addition to one or more organic electroluminescent compounds of the formula (1). The dopant used in the organic electric field light-emitting device of the present invention is not particularly limited.

較佳者，本發明之有機電場發光裝置中使用的摻雜劑可選自化學式(2)至(4)表示之化合物：Preferably, the dopant used in the organic electric field light-emitting device of the present invention may be selected from the compounds represented by the chemical formulas (2) to (4):

其中，Ar11 及Ar12 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C4-C30)雜芳基、經取代或未經取代之(C6-C30)芳基胺基、(C1-C30)烷基胺基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基，或與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基，或者，Ar11 及Ar12 藉由具有或不具稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯以形成脂環、或單環或多環之芳環；於c為1時，Ar13 表示經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C4-C30)雜芳基或選自下列結構之取代基：Wherein Ar 11 and Ar 12 independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (C4- C30) a heteroaryl group, a substituted or unsubstituted (C6-C30) arylamino group, a (C1-C30)alkylamino group, a substituted or unsubstituted 5 to 7 membered heterocycloalkyl group, and One or more substituted or unsubstituted aromatic rings fused 5 to 7 membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted with one or more Unsubstituted aromatic ring fused (C3-C30) cycloalkyl, or Ar 11 and Ar 12 by (C3-C30) alkyl or (C3-C30) alkyl with or without a fused ring a base linkage to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when c is 1, Ar 13 represents a substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted ( C4-C30) a heteroaryl group or a substituent selected from the following structures:

於c為2時，Ar13 表示經取代或未經取代之(C6-C30)伸芳基、經取代或未經取代之(C4-C30)伸雜芳基或選自下列結構之取代基：When c is 2, Ar 13 represents a substituted or unsubstituted (C6-C30) extended aryl group, a substituted or unsubstituted (C4-C30) heteroaryl group or a substituent selected from the following structures:

Ar14 及Ar15 獨立地表示經取代或未經取代之(C6-C30)伸芳基或經取代或未經取代之(C4-C30)伸雜芳基；R201 至R203 獨立地表示氫、氘、經取代或未經取代之(C1-C30)烷基，或經取代或未經取代之(C6-C30)芳基；d表示從1至4之整數；e表示0或1之整數；以及Ar 14 and Ar 15 independently represent a substituted or unsubstituted (C6-C30) extended aryl group or a substituted or unsubstituted (C4-C30) heteroaryl group; R 201 to R 203 independently represent hydrogen , hydrazine, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; d represents an integer from 1 to 4; e represents an integer of 0 or 1. ;as well as

其中，R211 至R214 獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C3-C30)雜芳基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基、與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基、氰基、NR301 R302 、BR303 R304 、PR305 R306 、P(=O)R307 R308 [其中，R301 至R308 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C3-C30)雜芳基]、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C1-C30)烷基硫基、經取代或未經取代之(C6-C30)芳氧基、經取代或未經取代之(C6-C30)芳硫基、經取代或未經取代之(C1-C30)烷氧基羰基、經取代或未經取代之(C1-C30)烷基羰基、經取代或未經取代之(C6-C30)芳基羰基、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(C6-C30)芳氧基羰基、經取代或未經取代之(C1-C30)烷氧基羰氧基、經取代或未經取代之(C1-C30)烷基羰氧基、經取代或未經取代之(C6-C30)芳基羰氧基、經取代或未經取代之(C6-C30)芳氧基羰氧基、羧基、硝基或羥基，或者，它們各自可藉由具有或不具有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或多環之芳環。Wherein R 211 to R 214 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted Substituted (C3-C30)heteroaryl, substituted or unsubstituted 5 to 7 membered heterocycloalkyl, 5 to 7 membered with one or more substituted or unsubstituted aromatic rings Cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkyl, (C3-C30)cycloalkyl, cyano, NR fused to one or more substituted or unsubstituted aromatic rings 301 R 302 , BR 303 R 304 , PR 305 R 306 , P(=O)R 307 R 308 [wherein R 301 to R 308 independently represent a substituted or unsubstituted (C1-C30) alkyl group, Substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30)heteroaryl], substituted or unsubstituted tri(C1-C30)alkyldecane, Substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)aryldecyl, substituted or unsubstituted tris(C6-C30)aryldecyl, substituted or unsubstituted (C6-C30) aryl(C1-C30)alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted Or unsubstituted (C1-C30)alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6-C30) arylthio, substituted or Unsubstituted (C1-C30) alkoxycarbonyl, substituted or unsubstituted (C1-C30) alkylcarbonyl, substituted or unsubstituted (C6-C30) arylcarbonyl, substituted or not Substituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (C1-C30) alkoxycarbonyloxy, substituted or unsubstituted (C1-C30)alkylcarbonyloxy, substituted or unsubstituted (C6-C30) arylcarbonyloxy, substituted Or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxy, nitro or hydroxy, or each of which may be (C3-C30) alkyl or (C3) with or without a fused ring -C30) an alkenyl group bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring.

電場發光層為產生電場發光處，而且可由單層或雙層或更多層形成。當使用如本發明之主體-摻雜劑系統時，如本發明之電場發光主體對發光效率提供了顯著的提升。摻雜濃度可為0.5至10 wt%。與其他現存主體材料相比時，如本發明之電場發光主體提供了優異的電洞及電子傳導率，以及極優越的穩定性與顯著提升的發光效率和操作壽命。The electric field luminescent layer is for generating an electric field illuminating portion, and may be formed of a single layer or two or more layers. When a host-dopant system as in the present invention is used, the electroluminescent body of the present invention provides a significant improvement in luminous efficiency. The doping concentration may be from 0.5 to 10 wt%. When compared to other existing host materials, the electroluminescent body of the present invention provides excellent hole and electron conductivity, as well as excellent stability and significantly improved luminous efficiency and operational life.

化學式(3)或化學式(4)表示之摻雜劑化合物可由第10-2009-0023442號韓國專利申請案中揭露之化合物例示之。更佳者，其可選自下列結構，但不限於此：The dopant compound represented by the chemical formula (3) or the chemical formula (4) can be exemplified by the compound disclosed in Korean Patent Application No. 10-2009-0023442. More preferably, it may be selected from the following structures, but is not limited thereto:

除了化學式(1)所示之有機電場發光化合物之外，本發明之有機電場發光裝置可同時更進一步包括一種或多種選自芳基胺化合物以及苯乙烯基芳基胺(styrylarylamine)化合物組成之群組之化合物。芳基胺化合物或苯乙烯基芳基胺化合物可以第10-2008-0123276、10-2008-0107606或10-2008-0118428號韓國專利申請案中揭露者例示之，但不限於此。In addition to the organic electroluminescent compound of the formula (1), the organic electroluminescent device of the present invention may further comprise one or more groups selected from the group consisting of arylamine compounds and styryl arylamine compounds. Group of compounds. The arylamine compound or the styrylarylamine compound can be exemplified by the Korean Patent Application No. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.

再者，在本發明之有機電場發光裝置中，除了化學式(1)所示之有機電場發光化合物之外，有機層可更進一步包括一種或多種選自第1族之有機金屬、第2族、第4週期與第5週期之過渡金屬、鑭系金屬與d-過渡元素(d-transition elements)組成之群組之金屬。Furthermore, in the organic electroluminescence device of the present invention, in addition to the organic electroluminescent compound of the formula (1), the organic layer may further comprise one or more organometallics selected from the group 1, the second group, A metal of a group consisting of transition metals, lanthanide metals, and d-transition elements of the fourth and fifth cycles.

再者，除了該有機電場發光化合物之外，該有機層可包括一層或多層有機電場發光層，該有機電場發光層同時發射藍、綠或紅光，以達成發白光之有機電場發光裝置。該發射藍、綠或紅光之化合物可以第10-2008-0123276、10-2008-0107606或10-2008-0118428號韓國專利申請案中所揭露者例示，但不限於此。Furthermore, in addition to the organic electroluminescent compound, the organic layer may comprise one or more layers of an organic electroluminescent layer that simultaneously emits blue, green or red light to achieve an organic light-emitting device that emits white light. The compound which emits blue, green or red light can be exemplified by the Korean Patent Application No. 10-2008-0123276, 10-2008-0107606, or 10-2008-0118428, but is not limited thereto.

在本發明之有機電場發光裝置中，可將選自硫屬元素化合物層(chalcogenide layer)、金屬鹵化物層以及金屬氧化物層的層體(後文後稱為“表面層”)設置於電極對中的一個或二個電極之內表面。更明確地說，矽或鋁之硫屬元素化合物(包括氧化物)層可設置於電場發光介質層的陽極表面，且金屬鹵化物層或金屬氧化物層可設置於該電場發光介質層的陰極表面。可由此得到操作穩定性。In the organic electric field light-emitting device of the present invention, a layer body selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") may be provided on the electrode. The inner surface of one or both of the electrodes. More specifically, a chalcogen compound (including oxide) layer of bismuth or aluminum may be disposed on the anode surface of the electric field luminescent medium layer, and a metal halide layer or a metal oxide layer may be disposed on the cathode of the electric field luminescent medium layer. surface. Operational stability can thus be obtained.

硫屬元素化合物可為，例如，SiOx (1x2)、AlOx (1x1.5)、SiON、SiAlON等。金屬鹵化物可為，例如，LiF、MgF2 、CaF2 、稀土金屬氟化物等。金屬氧化物可為例如，Cs2 O、Li2 O、MgO、SrO、BaO、CaO等。The chalcogen compound can be, for example, SiO x (1 x 2), AlO x (1 x 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride or the like. The metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO or the like.

在根據本發明之有機電場發光裝置中，較佳者亦可於電極對之至少一表面安置如是所製造之電子傳輸化合物與還原摻雜劑之混合區，或電洞傳輸化合物與氧化摻雜劑之混合區。在此種情形時，由於電子傳輸化合物還原成陰離子，加速電子從混合區注入與傳輸至電場發光介質。此外，由於電洞傳輸化合物氧化成陽離子，加速電洞從混合區注入與傳輸至電場發光介質。較佳的氧化摻雜劑包括各種路易士酸(Lewis acid)及接受體化合物(acceptor compound)。較佳的還原摻雜劑包括鹼金屬、鹼金屬化合物、鹼土金屬、稀土金屬，及其混合物。In the organic electric field light-emitting device according to the present invention, it is preferable that a mixed region of the electron transporting compound and the reducing dopant, or a hole transporting compound and an oxidizing dopant, may be disposed on at least one surface of the electrode pair. Mixed area. In this case, as the electron transporting compound is reduced to an anion, electrons are injected and transported from the mixing zone to the electric field illuminating medium. In addition, since the hole transport compound is oxidized to a cation, the accelerating hole is injected and transported from the mixing zone to the electric field illuminating medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof.

再者，具有二層或更多層之電場發光層之發白光之有機電場發光裝置，可藉由使用還原摻雜層作電荷產生層而製造之。Further, an organic electric field light-emitting device which emits white light having two or more layers of an electric field light-emitting layer can be manufactured by using a reduced doping layer as a charge generating layer.

有利效果Favorable effect

由於根據本發明之有機電場發光化合物具有良好的發光效率與優質的操作壽命，其可使用於製造具非常優異操作壽命之OLED裝置。Since the organic electroluminescent compound according to the present invention has good luminous efficiency and excellent operational life, it can be used for manufacturing an OLED device having a very excellent operational life.

發明模式Invention mode

本發明係藉由參照本發明之有機電場發光化合物、其製備方法，以及使用該化合物之裝置的電場發光特性進一步加以說明。然而，接下來的實施例係提供作為說明之目的，並無限制本發明範圍之意圖。The present invention is further illustrated by reference to the organic electroluminescent compound of the present invention, a method for producing the same, and an electric field luminescence property of a device using the compound. However, the following examples are provided for illustrative purposes and are not intended to limit the scope of the invention.

[製備例1]化合物1的製備[Preparation Example 1] Preparation of Compound 1

化合物1-1的製備Preparation of Compound 1-1

將2,7-二溴基萘(2,7-dibromonaphthalene)(20公克(g)，128.02毫莫耳(mmol))溶解於DMF(200毫升(mL))中。接著，在室溫下緩慢地加入NBS(50.1 g,281.65 mmol)。室溫下攪拌24小時後，在減壓下蒸餾此有機溶劑。加入蒸餾水後，用EA萃取獲得化合物1-1(36 g，114.64 mmol，89.56%)。2,7-dibromonaphthalene (20 g (g), 128.02 mmol (mmol)) was dissolved in DMF (200 mL (mL)). Next, NBS (50.1 g, 281.65 mmol) was slowly added at room temperature. After stirring at room temperature for 24 hours, the organic solvent was distilled under reduced pressure. After adding distilled water, extraction with EA gave Compound 1-1 (36 g, 114.64 mmol, 89.56%).

化合物1-2的製備Preparation of Compound 1-2

將化合物1-1(36 g，114.64 mmol)、苯基硼酸(phenylboronic acid)(41.9 g，343.92 mmol)、肆(三苯基膦)鈀(tetrakis(triphenylphosphine)palladium)(Pd(PPh3 )4 ，6.6 g，5.73 mmol)、3 M K2 CO3 (115 mL)、甲苯(500 mL)與乙醇(200 mL)混合，接著在回流下攪拌。經6小時反應接著冷卻至室溫後，加入蒸餾水。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1-2(29 g，94.02 mmol，82.48%)。Compound 1-1 (36 g, 114.64 mmol), phenylboronic acid (41.9 g, 343.92 mmol), tetrakis (triphenylphosphine) palladium (Pd(PPh 3 ) 4 , 6.6 g, 5.73 mmol), 3 MK 2 CO 3 (115 mL), toluene (500 mL) and ethanol (200 mL), and then stirred under reflux. After 6 hours of reaction and then cooled to room temperature, distilled water was added. After extracting with EA and drying over MgSO 4 , and then evaporated under reduced pressure, then Compound 1-2 (29 g, 94.02 mmol, 82.48%).

化合物1-3的製備Preparation of Compound 1-3

將KMnO4 (74.2 g，470.13 mmol)與蒸餾水(70 mL)混合，然後將吡啶(400 mL)與化合物1-2(29 g)加入其中。加熱至130 O C後，將KMnO4 (20 g)與蒸餾水(60 mL)間隔30分鐘加入4次。5小時之後，加入400 mL蒸餾水，並在回流下攪拌此混合物12小時。趁熱在減壓下過濾此反應混合物，接著用蒸餾水清洗之。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1-3(16 g，43.43 mmol，46.20%)。KMnO 4 (74.2 g, 470.13 mmol) was mixed with distilled water (70 mL), then pyridine (400 mL) and compound 1-2 (29 g) were added. After heating to 130 O C, KMnO 4 (20 g) was added 4 times with distilled water (60 mL) for 30 minutes. After 5 hours, 400 mL of distilled water was added, and the mixture was stirred under reflux for 12 hours. The reaction mixture was filtered under reduced pressure while hot, and then washed with distilled water. After extracting with EA and drying over MgSO 4 , EtOAc EtOAc m.

化合物1-4的製備Preparation of Compound 1-4

將化合物1-3(16 g，43.43 mmol)溶解於甲醇(300 mL)中，然後在室溫下緩慢地加入SOCl2 。在回流下攪拌12小時後，加入蒸餾水。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1-4(9 g，22.70 mmol，52.79%)。Compound 1-3 (16 g, 43.43 mmol) was dissolved in methanol (300 mL) then SOCI 2 was slowly added at room temperature. After stirring under reflux for 12 hours, distilled water was added. After extracting with EA and drying over MgSO 4 , EtOAc was evaporated.

化合物1-5的製備Preparation of Compound 1-5

將化合物1-4(9 g，22.70 mmol)溶解於THF(400 mL)中，然後在室溫下緩慢地加入溴化甲鎂(53 mL，158.91 mmol，3.0 M於二乙醚中)。在60 O C下攪拌12小時後，緩慢地加入蒸餾水。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1-5(5.6 g，14.12 mmol，62.21%)。Compound 1-4 (9 g, 22.70 mmol) was dissolved in THF (400 mL) then EtOAc (EtOAc, EtOAc, After stirring at 60 O C 12 hours, and distilled water was added slowly. After extracting with EA and drying over MgSO 4 , EtOAc EtOAc (EtOAc)

化合物1-6的製備Preparation of Compound 1-6

將化合物1-5(5.6 g,14.12 mmol)、乙酸(100 mL)及H3 PO4 (200 mL)混合，然後在回流下攪拌。經過10小時，冷卻至室溫後，加入蒸餾水。用NaOH水溶液中和之後，用EA萃取並用MgSO4乾燥後，在減壓下蒸餾，接著以管柱層析法獲得化合物1-6(2.5 g，6.93 mmol，49.11%)。Compound 1-5 (5.6 g, 14.12 mmol) , acetic acid (100 mL) and the mixture H 3 PO 4 (200 mL), followed by stirring under reflux. After 10 hours, after cooling to room temperature, distilled water was added. After neutralizing with an aqueous NaOH solution, the mixture was extracted with EtOAc and dried over MgSO 4 and evaporated.

化合物1-7的製備Preparation of Compound 1-7

將化合物1-6(2.5 g，6.93 mmol)溶解於THF(50 mL)中，然後加入NBS(1.35 g，7.62 mmol)。經過12小時攪拌後，令此有機溶劑在減壓下蒸餾。以管柱分離法獲得化合物1-7(2.7 g，6.14 mmol，88.67%)。Compound 1-6 (2.5 g, 6.93 mmol) was dissolved in THF (50 mL) then NBS (l. After stirring for 12 hours, the organic solvent was distilled under reduced pressure. Compound 1-7 (2.7 g, 6.14 mmol, 88.67%) was obtained by column chromatography.

化合物1的製備Preparation of Compound 1

將化合物1-7(2.7 g，6.14 mmol)、9-苯基-10-蒽硼酸(2.19 g，7.37 mmol)、肆(三苯基膦)鈀(Pd(PPh3 )4 ，0.35 g，0.30 mmol)、3 M K2 CO3 水溶液(6 mL)、甲苯(40 mL)以及乙醇(15 mL)混合，然後在回流下攪拌。經過8小時反應及冷卻至室溫後，加入蒸餾水。用EA萃取並用MgSO4 乾燥後，在減壓下蒸餾，接著以管柱分離法獲得化合物1(2.4 g，3.91 mmol，63.78%)。Compound 1-7 (2.7 g, 6.14 mmol), 9-phenyl-10-indoleboronic acid (2.19 g, 7.37 mmol), hydrazine (triphenylphosphine) palladium (Pd(PPh 3 ) 4 , 0.35 g, 0.30 Methyl), 3 MK 2 CO 3 aqueous solution (6 mL), toluene (40 mL), and ethanol (15 mL) were mixed and then stirred under reflux. After 8 hours of reaction and cooling to room temperature, distilled water was added. After extracting with EA and drying over MgSO 4 , and then evaporated under reduced pressure, then Compound 1 (2.4 g, 3.91 mmol, 63.78%).

化合物1至102係按照製備例1的步驟製備而成。藉此製成的有機電場發光化合物之1 H NMR及MS/FAB數據列示於表1之中。Compounds 1 to 102 were prepared in accordance with the procedure of Preparation 1. The 1 H NMR and MS/FAB data of the organic electroluminescent compound thus produced are shown in Table 1.

[實施例1]　使用本發明之有機電場發光化合物之OLED裝置之製造[Example 1] Manufacture of an OLED device using the organic electroluminescent compound of the present invention

用根據本發明之有機電場發光化合物製造了OLED裝置。An OLED device is fabricated using an organic electroluminescent compound according to the present invention.

首先，對獲得自OLED用玻璃(Samsung Corning製造)之透明電極ITO薄膜，依序用三氯乙烯、丙酮、乙醇及蒸餾水施以超音波清洗，並存放於異丙醇中備用。First, a transparent electrode ITO film obtained from OLED glass (manufactured by Samsung Corning) was subjected to ultrasonic cleaning with trichloroethylene, acetone, ethanol, and distilled water in that order, and stored in isopropyl alcohol for use.

接著，將ITO基材安置於真空氣相沉積設備的基材夾中，並將4,4’,4"-參(N,N-(2-萘基)-苯基胺基)三苯基胺(2-TNATA)置於真空氣相沉積設備之一小室(cell)中，接著換氣至腔室內真空至10-6 托(torr)。然後，施加電流至小室以蒸發2-TNATA，藉以在ITO基材上形成具有60 nm厚度之電洞注入層。Next, the ITO substrate is placed in a substrate holder of a vacuum vapor deposition apparatus, and 4,4',4"-parameter (N,N-(2-naphthyl)-phenylamino)triphenyl The amine (2-TNATA) is placed in a cell of a vacuum vapor deposition apparatus, and then ventilated to a vacuum in the chamber to 10 -6 torr. Then, a current is applied to the chamber to evaporate 2-TNATA. A hole injection layer having a thickness of 60 nm was formed on the ITO substrate.

接著，在真空氣相沉積設備之另一個小室中放入N,N’-雙(α-萘基)-N,N’-二苯基-4,4’-二胺(NPB)，並且施加電流至小室以蒸發NPB，藉以在電洞注入層上形成具有20 nm厚度之電洞傳輸層。Next, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another chamber of the vacuum vapor deposition apparatus, and applied. A current is passed to the chamber to evaporate the NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.

在形成電洞注入層和電洞傳輸層之後，如下所述於其上形成電場發光層。將化合物83置入真空氣相沉積設備作為主體，並將化合物E置入另一個小室作為摻雜劑。將此兩種材料以不同速率蒸發，以使具有30nm厚度之電場發光層(以主體為基礎計摻雜2至5wt%)氣相沉積於電洞傳輸層上。After the hole injection layer and the hole transport layer are formed, an electric field light-emitting layer is formed thereon as described below. Compound 83 was placed in a vacuum vapor deposition apparatus as a main body, and Compound E was placed in another chamber as a dopant. The two materials were evaporated at different rates to vapor-deposit an electroluminescent layer (2 to 5 wt% doped on a bulk basis) having a thickness of 30 nm on the hole transport layer.

之後，氣相沉積具有20 nm厚度之參(8-羥基喹啉)鋁(III)(Alq)作為電子傳輸層。接下來，氣相沉積具有1至2 nm厚度之8-羥基喹啉鋰(lithium quinolate，Liq)作為電子注入層。使用另一個真空氣相沉積設備形成具有150 nm厚度之鋁(Al)陰極以製造OLED。Thereafter, ginseng (8-hydroxyquinoline)aluminum (III) (Alq) having a thickness of 20 nm was vapor-deposited as an electron transport layer. Next, lithium quinolate (Liq) having a thickness of 1 to 2 nm was vapor-deposited as an electron injecting layer. An aluminum (Al) cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to fabricate an OLED.

OLED中所使用的各化合物係在10-6 torr下藉由真空昇華純化者。Each compound used in the OLED was purified by vacuum sublimation at 10 -6 torr.

[實施例2]使用本發明之有機電場發光化合物之OLED裝置之製造[Example 2] Manufacture of an OLED device using the organic electroluminescent compound of the present invention

根據實施例1的步驟製造了OLED裝置，不同的是用化合物3及化合物A取代電場發光層中的化合物83及化合物E。An OLED device was fabricated according to the procedure of Example 1, except that Compound 83 and Compound A were substituted for Compound 83 and Compound E in the electroluminescent layer.

[比較例1]使用現存的電場發光材料之OLED裝置之製造[Comparative Example 1] Manufacture of an OLED device using an existing electric field luminescent material

根據實施例1的步驟製造了OLED裝置，不同的是將二萘基蒽(DNA)放入真空氣相沉積設備中作為主體材料取代本發明之化合物。An OLED device was fabricated according to the procedure of Example 1, except that dinaphthyl fluorene (DNA) was placed in a vacuum vapor deposition apparatus as a host material in place of the compound of the present invention.

[比較例2]使用現存的電場發光材料之OLED裝置之製造。[Comparative Example 2] Production of an OLED device using an existing electroluminescent material.

根據實施例2的步驟製造了OLED裝置，不同的是將DNA放入真空氣相沉積設備中作為主體材料取代本發明之化合物。An OLED device was fabricated according to the procedure of Example 2, except that the DNA was placed in a vacuum vapor deposition apparatus as a host material in place of the compound of the present invention.

於1,000燭光/平方米(cd/m2 )測量實施例1與2以及比較例1與2中製造之OLED裝置的功率效率。其結果列於表2之中。The power efficiencies of the OLED devices fabricated in Examples 1 and 2 and Comparative Examples 1 and 2 were measured at 1,000 candelas per square meter (cd/m 2 ). The results are shown in Table 2.

從表2可見，當使用於綠色或藍色發射電場發光裝置中時，相較於比較例1與2，本發明之有機電場發光化合物提供經改善功率效率，同時也維持了可相比擬或較佳的色純度。As can be seen from Table 2, when used in a green or blue emission electric field illuminating device, the organic electroluminescent compound of the present invention provides improved power efficiency compared to Comparative Examples 1 and 2, while maintaining comparable or comparable Good color purity.

Claims (8)

一種有機電場發光化合物，係由化學式(1)所示： 其中，R1 至R18 獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、與一個或多個經取代或未經取代之(C3-C30)環烷基稠合之經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C3-C30)雜芳基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基、與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基、氰基、NR21 R22 、BR23 R24 、PR25 R26 、P(=O)R27 R28 [其中，R21 至R28 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C3-C30)雜芳基]、Ra Rb Rc Si-[其中，Ra 、Rb 、Rc 獨立地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]、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、Rd Y-[其中，Y表示S或O，且Rd 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]、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、Re C(=O)-[其中，Re 表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C6-C30)芳氧基]、Rf C(=O)O-[其中，Rf 表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C6-C30)芳氧基]、羧基、硝基、 或羥基，或者，它們可藉由具有或不具有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或多環之芳環；A、B以及W獨立地表示-(CR51 R52 )m -、-(R51 )C=C(R52 )-、-N(R53 )-、-S-、-O-、-Si(R54 )(R55 )-、-P(R56 )-、-P(=O)(R57 )-、-C(=O)-或-B(R58 )-，其中，R51 至R58 及R61 至R63 相同於R1 至R18 ；該雜環烷基及雜芳基可含一個或多個選自B、N、O、S、P(=O)、Si及P之雜原子；以及m表示1或2之整數。An organic electroluminescent compound is represented by the chemical formula (1): Wherein R 1 to R 18 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, and one or more Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, a substituted or unsubstituted 5 to 7 membered heterocycloalkyl group, a 5 to 7 membered heterocycloalkyl group fused to one or more substituted or unsubstituted aromatic rings, substituted or unsubstituted ( C3-C30) cycloalkyl, (C3-C30)cycloalkyl fused to one or more substituted or unsubstituted aromatic rings, cyano, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P(=O)R 27 R 28 [wherein, R 21 to R 28 independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group. Or a substituted or unsubstituted (C3-C30)heteroaryl], R a R b R c Si-[wherein, R a , R b , R c independently represent substituted or unsubstituted ( C1-C30)alkyl, or substituted or unsubstituted (C6-C30) aryl], substituted or unsubstituted (C6-C30) aryl (C1- C30) alkyl, R d Y- [wherein Y represents S or O, and R d represents a substituted or unsubstituted (C1-C30) alkyl group or a substituted or unsubstituted (C6-C30) aryl group. (C2-C30)alkenyl, substituted or unsubstituted (C2-C30)alkynyl, R e C(=O)-[wherein R e represents substituted or Unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C6-C30) aryloxy], R f C(=O)O-[wherein, R f represents a substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C1 -C30) alkoxy, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C6-C30) aryloxy], carboxyl, nitro, Or a hydroxy group, or they may be bonded to an adjacent substituent by a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form an alicyclic ring, or a monocyclic ring or Polycyclic aromatic rings; A, B and W independently represent -(CR 51 R 52 ) m -, -(R 51 )C=C(R 52 )-, -N(R 53 )-, -S-, -O-, -Si(R 54 )(R 55 )-, -P(R 56 )-, -P(=O)(R 57 )-, -C(=O)- or -B(R 58 ) - wherein R 51 to R 58 and R 61 to R 63 are the same as R 1 to R 18 ; the heterocycloalkyl and heteroaryl group may contain one or more selected from the group consisting of B, N, O, S, P ( =O), heteroatoms of Si and P; and m represents an integer of 1 or 2. 如申請專利範圍第1項所述之有機電場發光化合物，其中，R1 至R18 、R21 至R28 、R51 至R58 及R61 至R63 定義中的“經取代或未經取代”之取代基係獨立地更進一步經一個或多個選自氫、氘、鹵素、具有或不具鹵素取代基之(C1-C30)烷基、(C6-C30)芳基、具有或不具(C6-C30)芳基取代基之(C3-C30)雜芳基、5至7元雜環烷基、與一個或多個芳環稠合之5至7元雜環烷基、(C3-C30)環烷基、與一個或多個芳環稠合之(C3-C30)環烷基、三(C1-C30)烷基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷基、三(C6-C30)芳基矽烷基、(C2-C30)烯基、(C2-C30)炔基、氰基、咔唑基、NR31 R32 、BR33 R34 、PR35 R36 、P(=O)R37 R38 [其中，R31 至R38 獨立地表示(C1-C30)烷基、(C6-C30)芳基或(C3-C30)雜芳基]、(C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳基、(C1-C30)烷氧基、(C1-C30)烷基硫基、(C6-C30)芳氧基、(C6-C30)芳硫基、(C1-C30)烷氧基羰基、(C1-C30)烷基羰基、(C6-C30)芳基羰基、(C6-C30)芳氧基羰基、(C1-C30)烷氧基羰氧基、(C1-C30)烷基羰氧基、(C6-C30)芳基羰氧基、(C6-C30)芳氧基羰氧基、羧基、硝基以及羥基組成之群組之取代基取代；或者，其係鍵聯至相鄰取代基以形成環。The organic electroluminescent compound according to claim 1, wherein the substituted or unsubstituted R 1 to R 18 , R 21 to R 28 , R 51 to R 58 and R 61 to R 63 are defined. The substituents are independently further passed through one or more (C1-C30)alkyl groups, (C6-C30) aryl groups selected from hydrogen, deuterium, halogen, with or without a halogen substituent, with or without (C6) -C30) (C3-C30)heteroaryl group of a aryl substituent, 5- to 7-membered heterocycloalkyl group, 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings, (C3-C30) a cycloalkyl group, a (C3-C30) cycloalkyl group fused to one or more aromatic rings, a tri(C1-C30)alkyldecane group, a di(C1-C30)alkyl (C6-C30) aryl decane Base, tris(C6-C30)aryldecyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, oxazolyl, NR 31 R 32 , BR 33 R 34 , PR 35 R 36 , P(=O)R 37 R 38 [wherein, R 31 to R 38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl], (C6- C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C6-C30 Aryloxy, (C6-C30) arylthio, (C1-C30) alkoxy (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyl Substituted by a substituent of the group consisting of an oxy group, a (C6-C30) arylcarbonyloxy group, a (C6-C30) aryloxycarbonyloxy group, a carboxyl group, a nitro group, and a hydroxyl group; or, it is bonded to an adjacent group Substituents to form a ring. 一種有機電場發光裝置，包含如申請專利範圍第1或2項所述之有機電場發光化合物。An organic electric field light-emitting device comprising the organic electroluminescent compound according to claim 1 or 2. 如申請專利範圍第3項所述之有機電場發光裝置，其包含第一電極；第二電極；以及一層或多層有機層，該有機層係設於該第一電極以及該第二電極之間，其中，該有機層包含一個或多個如申請專利範圍第1或2項所述之有機電場發光化合物及一個或多個由化學式(2)至(4)所示之摻雜劑： 其中，Ar11 及Ar12 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C4-C30)雜芳基、經取代或未經取代之(C6-C30)芳基胺基、(C1-C30)烷基胺基、經取代或未經取代之5至7元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基，或與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基，或者，Ar11 及Ar12 藉由具有或不具稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯以形成脂環、或單環或多環之芳環；於c為1時，Ar13 表示經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C4-C30)雜芳基或選自下列結構之取代基： 於c為2時，Ar13 表示經取代或未經取代之(C6-C30)伸芳基、經取代或未經取代之(C4-C30)伸雜芳基或選自下列結構之取代基： Ar14 及Ar15 獨立地表示經取代或未經取代之(C6-C30)伸芳基或經取代或未經取代之(C4-C30)伸雜芳基；R201 至R203 獨立地表示氫、氘、經取代或未經取代之(C1-C30)烷基，或經取代或未經取代之(C6-C30)芳基；d表示從1至4之整數；e表示0或1之整數；以及 其中，R211 至R214 獨立地表示氫、氘、鹵素、經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基、經取代或未經取代之(C3-C30)雜芳基、經取代或未經取代之5至7-元雜環烷基、與一個或多個經取代或未經取代之芳環稠合之5至7元雜環烷基、經取代或未經取代之(C3-C30)環烷基、與一個或多個經取代或未經取代之芳環稠合之(C3-C30)環烷基、氰基、NR301 R302 、BR303 R304 、PR305 R306 、P(=O)R307 R308 [其中，R301 至R308 獨立地表示經取代或未經取代之(C1-C30)烷基、經取代或未經取代之(C6-C30)芳基，或經取代或未經取代之(C3-C30)雜芳基]、經取代或未經取代之三(C1-C30)烷基矽烷基、經取代或未經取代之二(C1-C30)烷基(C6-C30)芳基矽烷基、經取代或未經取代之三(C6-C30)芳基矽烷基、經取代或未經取代之(C6-C30)芳基(C1-C30)烷基、經取代或未經取代之(C1-C30)烷氧基、經取代或未經取代之(C1-C30)烷基硫基、經取代或未經取代之(C6-C30)芳氧基、經取代或未經取代之(C6-C30)芳硫基、經取代或未經取代之(C1-C30)烷氧基羰基、經取代或未經取代之(C1-C30)烷基羰基、經取代或未經取代之(C6-C30)芳基羰基、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(C6-C30)芳氧基羰基、經取代或未經取代之(C1-C30)烷氧基羰氧基、經取代或未經取代之(C1-C30)烷基羰氧基、經取代或未經取代之(C6-C30)芳基羰氧基、經取代或未經取代之(C6-C30)芳氧基羰氧基、羧基、硝基或羥基；或者，它們各自可藉由具有或不具有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基鍵聯至相鄰取代基以形成脂環、或單環或多環之芳環。The organic electroluminescent device of claim 3, comprising: a first electrode; a second electrode; and one or more organic layers disposed between the first electrode and the second electrode, Wherein, the organic layer comprises one or more organic electroluminescent compounds according to claim 1 or 2 and one or more dopants represented by the chemical formulas (2) to (4): Wherein Ar 11 and Ar 12 independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted (C4- C30) a heteroaryl group, a substituted or unsubstituted (C6-C30) arylamino group, a (C1-C30)alkylamino group, a substituted or unsubstituted 5 to 7 membered heterocycloalkyl group, and One or more substituted or unsubstituted aromatic rings fused 5 to 7 membered heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted with one or more Unsubstituted aromatic ring fused (C3-C30) cycloalkyl, or Ar 11 and Ar 12 by (C3-C30) alkyl or (C3-C30) alkyl with or without a fused ring a base linkage to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; when c is 1, Ar 13 represents a substituted or unsubstituted (C6-C30) aryl group, substituted or unsubstituted ( C4-C30) a heteroaryl group or a substituent selected from the following structures: When c is 2, Ar 13 represents a substituted or unsubstituted (C6-C30) extended aryl group, a substituted or unsubstituted (C4-C30) heteroaryl group or a substituent selected from the following structures: Ar 14 and Ar 15 independently represent a substituted or unsubstituted (C6-C30) extended aryl group or a substituted or unsubstituted (C4-C30) heteroaryl group; R 201 to R 203 independently represent hydrogen , hydrazine, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; d represents an integer from 1 to 4; e represents an integer of 0 or 1. ;as well as Wherein R 211 to R 214 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted Substituted (C3-C30)heteroaryl, substituted or unsubstituted 5 to 7-membered heterocycloalkyl, 5 to 7 fused to one or more substituted or unsubstituted aromatic rings a heterocycloalkyl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a (C3-C30) cycloalkyl group fused to one or more substituted or unsubstituted aromatic rings, a cyano group, NR 301 R 302 , BR 303 R 304 , PR 305 R 306 , P(=O)R 307 R 308 [wherein R 301 to R 308 independently represent a substituted or unsubstituted (C1-C30) alkyl group, Substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30)heteroaryl], substituted or unsubstituted tri(C1-C30)alkyldecane , substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)aryldecyl, substituted or unsubstituted tris(C6-C30)aryldecyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, taken Or unsubstituted (C1-C30)alkylthio, substituted or unsubstituted (C6-C30) aryloxy, substituted or unsubstituted (C6-C30) arylthio, substituted or Unsubstituted (C1-C30) alkoxycarbonyl, substituted or unsubstituted (C1-C30) alkylcarbonyl, substituted or unsubstituted (C6-C30) arylcarbonyl, substituted or not Substituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C6-C30) aryloxycarbonyl, substituted or unsubstituted (C1-C30) alkoxycarbonyloxy, substituted or unsubstituted (C1-C30)alkylcarbonyloxy, substituted or unsubstituted (C6-C30) arylcarbonyloxy, substituted Or unsubstituted (C6-C30) aryloxycarbonyloxy, carboxy, nitro or hydroxy; or, each of which may be (C3-C30) alkyl or (C3) with or without a fused ring -C30) an alkenyl group bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring. 如申請專利範圍第4項所述之有機電場發光裝置，其中，該有機層包含一種或多種選自芳基胺化合物以及苯乙烯基芳基胺化合物組成之群組之化合物。The organic electroluminescent device of claim 4, wherein the organic layer comprises one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds. 如申請專利範圍第4項所述之有機電場發光裝置，其中，該有機層更進一步包括一種或多種選自第1族之有機金屬、第2族、第4週期與第5週期之過渡金屬、鑭系金屬與d-過渡元素組成之群組之金屬或錯化物。The organic electroluminescent device of claim 4, wherein the organic layer further comprises one or more organometallics selected from Group 1, Group 2, transition metals of Cycles 4 and 5, a metal or a compound of a group consisting of a lanthanide metal and a d-transition element. 如申請專利範圍第4項所述之有機電場發光裝置，其中，該有機層包含電場發光層以及電荷產生層。The organic electroluminescence device of claim 4, wherein the organic layer comprises an electric field luminescent layer and a charge generating layer. 如申請專利範圍第4項所述之有機電場發光裝置，其發白光有機電場發光裝置，其中，該有機層包含一層或多層同時發射紅、綠或藍光之有機電場發光層。An organic electric field light-emitting device according to claim 4, wherein the organic layer comprises one or more organic light-emitting layers that simultaneously emit red, green or blue light.
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