TWI507505B - Organic electroluminescent device using 2-methylanthracene compound - Google Patents

Organic electroluminescent device using 2-methylanthracene compound Download PDF

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TWI507505B
TWI507505B TW097141747A TW97141747A TWI507505B TW I507505 B TWI507505 B TW I507505B TW 097141747 A TW097141747 A TW 097141747A TW 97141747 A TW97141747 A TW 97141747A TW I507505 B TWI507505 B TW I507505B
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organic electroluminescent
electroluminescent device
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organic
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TW201016823A (en
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Shih Wen Wen
Hung Ming Guo
Kun Feng Chiang
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E Ray Optoelectronics Tech Co
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使用2-甲基蒽化合物之有機電激發光裝置Organic electroluminescent device using 2-methylindole compound

本案係有關於一種有機發光二極體及製造方法,更明確言之,係特別有關綠光有機發光二極體其具有優良的發光效率,亮度和色度。The present invention relates to an organic light-emitting diode and a manufacturing method thereof. More specifically, it relates to a green light-emitting organic light-emitting diode which has excellent luminous efficiency, brightness and chromaticity.

自從美國科達公司的鄧青雲博士報導了低驅動電壓的有機電激發光裝置之後(C.W.Tang,Applied Physics Letters,51,913,1987),就引起了有機化合物應用在有機電激發光裝置的研究熱潮,有機電激發光裝置係經由有機介質(medium)夾置在兩電極間(陽極和陰極),形成之三明治結構,其中,陽極為具高功函數之金屬或導電化合物,例如:ITO、IZO、SnO2、ZnO等類似之透明金屬氧化物,或可為poly-Si、a-Si等之TFT基材;而陰極為具低功函數之金屬或導電化合物,例如:Au、Al、In、Mg、Ca或類似之金屬、合金等;而兩電極中至少有一為透明或半透明的,以使發射光能有效率穿透。有機介質依情況不同可由數層組成,其中各層之厚度不被嚴格限制,通常在5 nm到5μm間,而代表性的為在兩電極間夾入三層有機分子層,此三層包括一個電子傳輸層,一個發光層及一個電洞傳輸層。通常為降低驅動電壓會另外加入電洞或電子注入層,或改善發光效率而增加電洞或電子阻絕層,而成為四到六個有機分子層所組成之有機電激發光裝置;其中電子注入層通常可由鹼金屬鹵化物或含氮、氧之鹼金屬螯合物,例如: LiF、8-quinolinolato lithium(Liq)等;而電洞注入層通常可由金屬苯二甲藍(Metal Phthalocyanine)衍生物、星狀polyamine衍生物、polyaniline衍生物(Y.Yang et al,Syn.Met.,1997,87,171)、全氟化物、SiO2(Z.B.Deng et al,Appl.Phys.Lett.,1997,74,2227)或電洞傳輸材料摻雜氧化物等,例如:CuPc(S.A.Vanslyke et al,Appl.Phys.Lett.,1996,69,2160)、MTDATA(Y.Shirota et al,Appl.Phys.Lett.,1994,65,807)、TPD+SbCl6-(A.Yamamori et al,Appl.Phys.Lett.,1998,72,2147)、PEDOT-PSS(A.Elschner et al,Syn.Met.,2000,111,139)等;電子傳輸層可由含氮、氧之金屬螯合物(T.Sano et al,J.Mater.Chem.,2000,10,157)、oxadiazole衍生物、全氟化多芳香環衍生物、芳香環或雜環取代之silole衍生物、oligothiophene衍生物或benzimidazole衍生物所組成,例如:tris(8-quinolinolato)aluminum(Alq3)、PBD(N.Johansson et al,Adv.Mater.,1998,10,1136)、PyPySiPyPy(M.Uchida et al,Chem.Mater.,2001,13,2680)、BMB-3T(T.Noda et al,Ady.Mater.,1999,11,283)、PF-6P(Y.Sakamoto et al,J.Amer.Chem.Soc.,2000,122,1832)、TPBI(Y.T.Tao et al,Appl.Phys.Lett.,2000,77,933)等;電洞傳輸層通常為用在有機光導材料中之對電洞的電荷傳輸材料所組成,此電荷傳輸材料可由triazole衍生物、oxadiazole衍生物、imidazole衍生物、phenylenediamine衍生物、星狀多胺類衍生物、spiro-linked分子衍生物或arylamine衍生物所組成,例如:NPB或其衍生物(Y.Sato et al,Syn.Met.,2000,111,25)、PTDATA (Y.Shirota et al,Syn.Met.,2000,111,387)、spiro-mTTB(U.Bach et al,Adv.Mater.,2000,12,1060)等。由於OLED具有低驅動電壓的特性並已驗證可應用到全彩平面顯示器上,故有機電激發光裝置與材料的研究已引起全世界的注意與投入。Since Dr. Deng Qingyun from Keda Company of the United States reported on low-voltage organic electroluminescent devices (CWTang, Applied Physics Letters, 51, 913, 1987), it has caused a research boom in the application of organic compounds to organic electroluminescent devices. The organic electroluminescent device is sandwiched between two electrodes (anode and cathode) via an organic medium to form a sandwich structure in which the anode is a metal having a high work function or a conductive compound such as ITO, IZO, SnO2 a transparent metal oxide such as ZnO or the like, or a TFT substrate such as poly-Si or a-Si; and the cathode is a metal or a conductive compound having a low work function, for example, Au, Al, In, Mg, Ca Or a similar metal, alloy, etc.; and at least one of the two electrodes is transparent or translucent so that the emitted light can penetrate efficiently. The organic medium may be composed of several layers depending on the case, wherein the thickness of each layer is not strictly limited, and is usually between 5 nm and 5 μm, and representatively, three layers of organic molecules are sandwiched between the two electrodes, and the three layers include one electron. Transport layer, a light-emitting layer and a hole transport layer. Usually, in order to reduce the driving voltage, a hole or an electron injecting layer is additionally added, or a light hole or an electron blocking layer is added to improve the luminous efficiency, and an organic electroluminescent device composed of four to six organic molecular layers is formed; wherein the electron injecting layer is formed. It is usually possible to use an alkali metal halide or a nitrogen-containing, oxygen-containing alkali metal chelate compound, for example: LiF, 8-quinolinolato lithium (Liq), etc.; and the hole injection layer can usually be derived from metal Phthalocyanine derivatives, star-shaped polyamine derivatives, polyaniline derivatives (Y.Yang et al, Syn.Met. , 1997, 87, 171), perfluorinated, SiO2 (ZBDeng et al, Appl. Phys. Lett., 1997, 74, 2227) or hole transport material doped oxides, etc., for example: CuPc (SAVanslyke et al, Appl. Phys. Lett., 1996, 69, 2160), MTDATA (Y. Shirota et al, Appl. Phys. Lett., 1994, 65, 807), TPD + SbCl6- (A. Yamamori et al, Appl. Phys. Lett., 1998, 72, 2147), PEDOT-PSS (A. Elschner et al, Syn. Met., 2000, 111, 139), etc.; the electron transport layer may be a metal chelate containing nitrogen and oxygen (T. Sano et al, J. Mater.Chem., 2000, 10, 157), an oxadiazole derivative, a perfluorinated polyaromatic ring derivative, an aromatic or heterocyclic substituted silole derivative, an oligothiophene derivative or a benzimidazole derivative, for example: tris (8- Quinolinolato)aluminum (Alq3), PBD (N. Johansson et al, Adv. Mater., 1998, 10, 1136), PyPySiPyPy (M. Uchida et al, Chem. Mater., 2001, 13, 2680), BMB-3T (T.Noda et al, Ady.Mater., 1999, 1 1,283), PF-6P (Y. Sakamoto et al, J. Amer. Chem. Soc., 2000, 122, 1832), TPBI (YTTao et al, Appl. Phys. Lett., 2000, 77, 933), etc.; The hole transport layer is usually composed of a charge transport material for a hole in an organic photoconductive material, which may be a triazole derivative, an oxadiazole derivative, an imidazole derivative, a phenylenediamine derivative, or a stellate polyamine derivative. , consisting of a spiro-linked molecular derivative or an arylamine derivative, for example, NPB or a derivative thereof (Y. Sato et al, Syn. Met., 2000, 111, 25), PTDATA (Y. Shirota et al, Syn. Met., 2000, 111, 387), spiro-mTTB (U. Bach et al, Adv. Mater., 2000, 12, 1060) and the like. Since OLEDs have low driving voltage characteristics and have been verified to be applicable to full color flat panel displays, research on organic electroluminescent devices and materials has attracted worldwide attention and investment.

為了改善有機電激發光裝置的發光顏色、發光效率、發光穩定性、元件壽命與元件製作方式等,這些改良成果可參閱已頒予之美國專利案第4,356,429號、第4,539,507號、第4,720,432號、第4,885,211號、第5,151,629號、第5,150,006號、第5,141,671號、第5,073,446號、第5,061,569號、第5,059,862號、第5,059,861號、第5,047,687號、第4,950,950號、第4,769,292號、第5,104,740號、第5,227,252號、第5,256,945號、第5,069,975號、第5,122,711號、第5,366,811號、第5,126,214號、第5,142,343號、第5,389,444號、第5,458,977號等。In order to improve the illuminating color, illuminating efficiency, illuminating stability, component life, and component manufacturing method of the organic electroluminescent device, the improvement results can be referred to the issued U.S. Patent Nos. 4,356,429, 4,539,507, 4,720,432. Nos. 4,885,211, 5,151,629, 5,150,006, 5,141,671, 5,073,446, 5,061,569, 5,059,862, 5,059,861, 5,047,687, 4,950,950, 4,769,292, 5,104,740, 5,227,252 No. 5,256,945, 5,069,975, 5,122,711, 5,366,811, 5,126,214, 5,142,343, 5,389,444, 5,458,977, and the like.

在綠色螢光摻雜物方面,鄧青雲等人對10-(1,3-benzothiazol-2-tl)-1,1,7,7-tetramethyl-2.3.6.7-tetrahydro-1H,5H,11H-pyrano-[2,3-f]pyrido[3,2,1-ij]quinolinllone(簡稱C545T)研究,發現此化合物微量(0.5%~1.0%之體積比)摻雜再主發光體中所製成的綠光元件,可以達到符合商業需求的良好性能,現在已有Kodak、Pioneer、Sanyo等公司將此化合物應用在有機發光二極體上。雖然降C545T摻雜在主發光體中所製成的綠光元件具有良好特性,但此種發光元件仍有一些缺點;特別是其最佳發光效率出現在C545T摻雜濃度約0.5%~1.0%之間,一旦過了此最佳濃度 之後,元件的發光效率便隨摻雜濃度的增加而大幅下降,這樣的特性使得元件製作時必須要十分精準控制C545T摻雜濃度。如此窄的濃度摻雜最佳化操作條件,對元件製造產生相當困難與不便。因為C545T的分子結構中,含氧雜環中3號與4號碳之間的雙鍵,是有可能經由光化學進行[2+2]環化反應,進而形成雙體,破壞了原本的發色團共振結構,造成了螢光的驟熄,才使得上述現象發生。In terms of green fluorescent dopants, Deng Qingyun et al. for 10-(1,3-benzothiazol-2-tl)-1,1,7,7-tetramethyl-2.3.6.7-tetrahydro-1H, 5H, 11H- Pyrano-[2,3-f]pyrido[3,2,1-ij]quinolinllone (C545T for short) was found to be a trace amount (0.5%~1.0% by volume) of the compound doped in the main illuminant. The green light components can achieve good performance in line with commercial requirements. Now Kodak, Pioneer, Sanyo and other companies have applied this compound to organic light-emitting diodes. Although the green light-emitting element made by the C545T doping in the main illuminant has good characteristics, such a light-emitting element still has some disadvantages; in particular, its optimum luminous efficiency occurs at a C545T doping concentration of about 0.5% to 1.0%. Between this, once this optimum concentration has passed After that, the luminous efficiency of the component is greatly reduced as the doping concentration increases. This characteristic makes it necessary to precisely control the C545T doping concentration when the component is fabricated. Such narrow concentration doping optimization operation conditions are quite difficult and inconvenient for component fabrication. Because of the molecular structure of C545T, the double bond between No. 3 and No. 4 carbon in the oxygen-containing heterocyclic ring is likely to undergo a [2+2] cyclization reaction via photochemistry, thereby forming a dimer, destroying the original chromophore. The resonance structure causes the quenching of the fluorescent light to cause the above phenomenon to occur.

為改善先前所發表的綠光摻雜物材料的缺點,本發明提出一綠光有機化合物,如式I所示,其中Y1 、Y2 、Y3 和Y4 各代表6至20個碳原子所組成取代或非取代之芳香族基團。To improve the disadvantages of previously published green light dopant materials, the present invention provides a green organic compound, as shown in Formula I, wherein Y 1 , Y 2 , Y 3 and Y 4 each represent 6 to 20 carbon atoms. A substituted or unsubstituted aromatic group is formed.

本發明另一個宗旨在於提供一具有高發光效率、飽和色純度和長元件操作穩定性之綠光有機電激發光元件裝置。此有機電激發光元件裝置其至少由一對電極所組成,介於兩電極間包含一陽極、一陰極和有機化合物所組成之單層或多層結構,而其中至少一有機層含有上述式I化合物。Another object of the present invention is to provide a green organic electroluminescent device device having high luminous efficiency, saturated color purity, and long device operational stability. The organic electroluminescent device is composed of at least one pair of electrodes, and comprises a single layer or a multi-layer structure composed of an anode, a cathode and an organic compound between the electrodes, wherein at least one organic layer contains the compound of the above formula I .

在有機電激發光元件裝置之發光層中,當本發明之綠 光有機化合物,如式I所示,以客發光體材料形式摻雜於一主發光體材料中,其可經由主客發光體材料間能量轉移或電子/電洞直接於客發光體中再結合的機制,減少非放光機制的產生而增高元件發光效率與操作穩定性,並且得到飽和色度高之綠光元件。客發光體材料之摻雜濃度對於主發光體可為0.01%至50%重量比之間,而較佳的摻雜濃度為0.5%至20%重量比。In the light-emitting layer of the organic electroluminescent device, when the green of the present invention a photoorganic compound, as shown in Formula I, is doped in a host illuminant material in the form of a guest illuminant material, which can be recombined directly into the guest illuminant via energy transfer between the host and guest illuminant materials or electron/holes. The mechanism reduces the generation of the non-light-emitting mechanism and increases the luminous efficiency and operational stability of the element, and obtains a green light element with high saturation chromaticity. The doping concentration of the guest illuminant material may be between 0.01% and 50% by weight for the main illuminant, and a preferred doping concentration is 0.5% to 20% by weight.

本發明之綠光有機化合物如式I所示,其主要可應用於有機電激發光元件裝置所需要的有機材料,當期作為發光材料時可得到一具有高發光效率、飽和色純度和長元件操作穩定性之綠光元件。The green organic compound of the present invention is as shown in Formula I, and is mainly applicable to an organic material required for an organic electroluminescent device, and a high luminous efficiency, saturated color purity, and long component can be obtained as a luminescent material in the current period. Green light component for operational stability.

本發明之綠光有機化合物,其取代與非取代之芳香族例子如:苯基、2-甲苯基、3-甲苯基、4-甲苯基、3,4-二甲苯基、萘基、和蒽基,但不僅限於此範疇。以下所列之化合物是本發明之綠光有機化合物較具代表性之例子,任何可以想到之相關衍生物將涵蓋於本發明的精神範圍。The green-light organic compound of the present invention, which is substituted and unsubstituted aromatic examples such as phenyl, 2-tolyl, 3-tolyl, 4-tolyl, 3,4-dimethylphenyl, naphthyl, and anthracene Base, but not limited to this category. The compounds listed below are representative of the green-light organic compounds of the present invention, and any concomitant related derivatives will be encompassed within the spirit of the present invention.

本發明可應用於數種不同的有激電機發光裝置中,而其中必要的組成是陰極、陽極以及其間之有機層,該有機層可以包含有電洞注入層、電洞傳輸層、發光層以及電子傳輸層;而如第一圖為最典型的結構,其中包括基板11,陽極12,非必須之電洞注入層13,電洞傳輸層14,發光層15,電子傳輸層16,電子注入層17,金屬陰極18及電源19,當施加電壓於兩電極之間時,陽極所產生之電洞以及陰極所產生之電子,會注入有機層中進而結合成激子(excitons),而當激子降至基態時便會散射出光。The invention can be applied to several different excitation motor light-emitting devices, wherein the necessary composition is a cathode, an anode and an organic layer therebetween, and the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, and The electron transport layer; as shown in the first figure, is the most typical structure, including the substrate 11, the anode 12, the unnecessary hole injection layer 13, the hole transport layer 14, the light-emitting layer 15, the electron transport layer 16, and the electron injection layer. 17, the metal cathode 18 and the power source 19, when a voltage is applied between the two electrodes, the holes generated by the anode and the electrons generated by the cathode are injected into the organic layer to be combined into excitons, and when excitons Light is scattered when it is lowered to the ground state.

而以下仔細描述這數層所使用之材料。首先必須注意的是,基板可選擇性的置於陰極旁邊,或基板可當成陽極或陰極,再者,所有有機層的總厚度最好小於500 nm。The materials used in these layers are described carefully below. It must first be noted that the substrate can be selectively placed next to the cathode, or the substrate can be an anode or a cathode, and further, the total thickness of all organic layers is preferably less than 500 nm.

須注意者,所屬領域中具有通常知識者可依習知之技藝或本發明說明書中所述之先前技術或現有之方法利用本發明所請之化合物製得有機電激發光元件或裝置。以下說明本發明有機電激發光元件或裝置中電洞注入層以外之各元件結構的適用材料。It is to be noted that those skilled in the art can make organic electroluminescent devices or devices using the compounds of the present invention in accordance with conventional techniques or prior art or prior art methods described in the present specification. Hereinafter, suitable materials for the structure of each element other than the hole injection layer in the organic electroluminescent device or device of the present invention will be described.

基板Substrate

基板可依據光所放射的方向為透光性或是不透明的,如果欲使EL發射由基板處觀察,則基板必須具有光穿透性,在這種情況下,一般都是使用玻璃或有機材料;而如果EL發射是欲透過上電極觀察的話,則下層支撐物的通光與否將變得無關緊要,因此可為光穿透、光吸收或光反射,此時,基板的材料可使用但不限制為玻璃、塑膠、 半導體材料、陶瓷和電路板材料,當然此種元件結構必須提供可透光的上電極。The substrate may be translucent or opaque depending on the direction in which the light is emitted. If the EL emission is to be observed from the substrate, the substrate must have light penetrability. In this case, glass or organic materials are generally used. And if the EL emission is to be observed through the upper electrode, the light passage of the lower support will become irrelevant, so it can be light penetration, light absorption or light reflection. At this time, the material of the substrate can be used but Not limited to glass, plastic, Semiconductor materials, ceramics, and circuit board materials, of course, such component structures must provide a light transmissive upper electrode.

陽極anode

導電陽極層通常製作於基板上,而當EL放射是透過陽極觀測的話,則陽極必須是透明的或大體上對於某些放射是可穿透的;使用於本發明的為一般常見的透明陽極-銦錫氧化物(indium tin oxide,ITO),但其他金屬氧化物仍是可使用的,包括但不限制於鋁或銦摻雜的鋅氧化物(indium doped zinc oxide,IZO)、鎂-銦氧化物(magnesium-indium oxide)和鎳-鎢氧化物(nickel-tungsten oxide),除了這些氧化物外,金屬氮化物,例如氮化鎵(gallium nitride),和金屬硒化物,例如硒化鋅(zinc selenide),和金屬硫化物,例如硫化鋅(zinc sulfide)都可使用於該層。對於EL放射是透過上電極而被觀測的應用中,該層的透光性不再重要,而可使用任何可導電的材料,透明的、不透明的、或反射的材料皆可,此應用下可使用的材料包括但不限制於金、銥、鉬、鈀和鉑。一般陽極材料,無論透明與否,其功函率通常大於或等於4.1 eV,所需要的陽極材料通常以適當的方式沈積,例如蒸鍍、濺鍍、化學氣相沈積、或電化學方法等,而陽極可用熟知的微影曝光方式(photolithography)蝕刻圖案化。The conductive anode layer is typically fabricated on a substrate, and when EL radiation is observed through the anode, the anode must be transparent or substantially transparent to certain radiation; a generally common transparent anode for use in the present invention - Indium tin oxide (ITO), but other metal oxides can still be used, including but not limited to aluminum or indium doped zinc oxide (IZO), magnesium-indium oxide Magnesium-indium oxide and nickel-tungsten oxide, in addition to these oxides, metal nitrides such as gallium nitride, and metal selenides such as zinc selenide (zinc) Selenide), and metal sulfides such as zinc sulfide can be used for this layer. In applications where EL radiation is observed through the upper electrode, the light transmission of the layer is no longer important, and any electrically conductive material, transparent, opaque, or reflective material can be used. Materials used include, but are not limited to, gold, ruthenium, molybdenum, palladium, and platinum. Generally, the anode material, whether transparent or not, has a work function of usually greater than or equal to 4.1 eV, and the required anode material is usually deposited in an appropriate manner, such as evaporation, sputtering, chemical vapor deposition, or electrochemical methods. The anode can be patterned by well-known photolithography etching.

電洞傳輸層(hole-transporting layer,HTL)Hole-transporting layer (HTL)

有機EL元件的電洞傳輸層至少包含一個電洞傳導化 合物,例如芳香三級胺,現今所推斷的是此種化合物至少要含有一個只鍵結在碳原子上的三價的氮原子,而此碳原子至少要有一個是芳香環的其中一員;這些芳香族三級胺的其中一種形式可以是芳基胺,例如單芳烴基胺、雙芳烴基胺、三芳烴基胺或是高分子的芳烴基胺基團;單分子型三芳烴基胺的典範由Klupfel等人描述於U.S.Pat.No.3,180,730;而其他適合的三芳烴基胺是由Brantley等人揭露於U.S.Pat.Nos.3,567,450和3,658,520,有關於一個或多個乙烯基自由基和/或包含至少一個容納有活性氫的基團取代的三芳烴基胺。The hole transport layer of the organic EL element includes at least one hole conduction Compounds, such as aromatic tertiary amines, it is inferred today that such compounds contain at least one trivalent nitrogen atom bonded only to a carbon atom, and at least one of the carbon atoms is one of the aromatic rings; One of these aromatic tertiary amines may be an arylamine such as a monoarylamine, a bisarylamine, a triarylamine or a high molecular aromatic amine group; a monomeric triarylamine A model is described by Klupfel et al. in US Pat. No. 3,180,730; and other suitable triarylamines are disclosed by Brantley et al. in US Pat. Nos. 3,567,450 and 3,658,520, relating to one or more vinyl radicals and/or Or a triarylalkylamine substituted with at least one group containing an active hydrogen.

最為人所使用的一種芳香族三級胺是由U.S.Pat.Nos.4,720,432和5,061,569所描述的:包含至少兩個芳香族三級胺基團的芳香族三級胺,以下列出的為有用的芳香族三級胺的例證:1,1-雙(4-二-對-甲苯基胺基苯基)環己烷,1,1-雙(4-二-對-甲苯基胺基苯基)-4-苯基-環己烷,4,4’-雙(二苯基胺基)四苯,雙(4-二甲基胺基-2-甲基苯基)-苯基甲烷,N,N,N-三(對-甲苯基)胺,4-(二-對-甲苯基胺基)-4’-[4(二-對-甲苯基胺基)-苯乙烯基]茋,N,N,N’,N’-四-對-甲苯基-4,4’-二胺基聯苯,N,N,N’,N’-四苯基-4,4’-二胺基聯苯,N,N,N’,N’-四-1-萘基-4,4’-二胺基聯苯,N,N,N’,N’-四-2-萘基-4,4’-二胺基聯苯, N-苯基咔唑,4,4’-雙[N-(1-萘基)-N-苯基胺基]聯苯,4,4’-雙[N-(1-萘基)-N-(2-萘基)胺基]聯苯,4,4’-雙[N-(1-萘基)-N-苯基胺基]對-聯三苯,4,4’-雙[N-(2-萘基)-N-苯基胺基]聯苯,1,5-雙[N-(1-萘基)-N-苯基胺基]萘,4,4’-雙[N-(9-蒽基)-N-苯基胺基]聯苯,4,4’-雙[N-(1-蒽基)-N-苯基胺基]對-聯三苯,4,4’-雙[N-(2-菲基)-N-苯基胺基]聯苯,4,4’-雙[N-(8-氟蒽烯基)-N-苯基胺基]聯苯,4,4’-雙[N-(2-pyrenyl)-N-苯基胺基]聯苯,4,4’-雙[N-(2-naphthacenyl)-N-苯基胺基]聯苯,4,4’-雙[N-(2-perylenyl)-N-苯基胺基]聯苯,4,4’-雙[N-(2-苛基)-N-苯基胺基]聯苯,2,6-雙(二-對-甲苯基胺基)萘,2,6-雙(二-(1-萘基)胺基)萘,2,6-雙[N-(1-萘基)-N-(2-萘基)胺基]萘,N,N,N’,N’-四(2-萘基)-4,4”-二胺基-對-聯三苯,4,4’-雙{N-苯基-N-[4-(1-萘基)-苯基]胺基}聯苯,4,4’-雙[N-苯基-N-(2-pyrenyl)胺基]聯苯,2,6-雙[N,N-二(2-萘基)胺基]茀,或1,5-雙[N-(1-萘基)-N-苯基胺基]萘。One of the most useful aromatic tertiary amines is described in US Pat. Nos. 4,720,432 and 5,061,569: aromatic tertiary amines containing at least two aromatic tertiary amine groups, the following are useful An example of an aromatic tertiary amine: 1,1-bis(4-di-p-tolylamidophenyl)cyclohexane, 1,1-bis(4-di-p-tolylaminophenyl) 4-phenyl-cyclohexane, 4,4'-bis(diphenylamino)tetraphenyl, bis(4-dimethylamino-2-methylphenyl)-phenylmethane, N, N,N-tris(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4(di-p-tolylamino)-styryl]indole, N, N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl ,N,N,N',N'-tetra-1-naphthyl-4,4'-diaminobiphenyl, N,N,N',N'-tetra-2-naphthyl-4,4' -diaminobiphenyl, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl, 4,4'-bis[N-(1-naphthyl)-N -(2-naphthyl)amino]biphenyl, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]p-terphenyl, 4,4'-double [N -(2-naphthyl)-N-phenylamino]biphenyl, 1,5-bis[N-(1-naphthyl)-N-phenylamino]naphthalene, 4,4'-double [N -(9-fluorenyl)-N-phenylamino]biphenyl, 4,4'-bis[N-(1-indenyl)-N-phenylamino]p-terphenyl, 4,4 '-Bis[N-(2-phenanthryl)-N-phenylamino]biphenyl, 4,4'-bis[N-(8-fluorodecenyl)-N-phenylamino]biphenyl ,4,4'-bis[N-(2-pyrenyl)-N-phenylamino]biphenyl, 4,4'-bis[N-(2-naphthacenyl)-N-phenylamino]biphenyl , 4,4'-bis[N-(2-perylenyl)-N-phenylamino]biphenyl, 4,4'-bis[N-(2-arginyl)-N-phenylamino] Benzene, 2,6-bis(di-p-tolylamino)naphthalene, 2,6-bis(di-(1-naphthyl)amino)naphthalene, 2,6-bis[N-(1-naphthalene) -N-(2-naphthyl)amino]naphthalene, N,N,N',N'-tetrakis(2-naphthyl)-4,4"-diamine -p-terphenylene, 4,4'-bis{N-phenyl-N-[4-(1-naphthyl)-phenyl]amino}biphenyl, 4,4'-bis[N-benzene Benzyl-N-(2-pyrenyl)amino]biphenyl, 2,6-bis[N,N-bis(2-naphthyl)amino]indole, or 1,5-bis[N-(1-naphthalene) Base) -N-phenylamino]naphthalene.

另一種有用的電洞傳輸材料為EP 1 009 041所描述的多環性芳香族化合物,此外,高分子型電洞傳輸材料也能被使用,如聚(N-乙烯基咔唑)(PVK)、聚噻吩、聚咇咯、聚 苯胺和共聚高分子,如聚(3,4-伸乙基二氧噻吩)/聚(4-苯乙烯-磺酸鹽)也被稱為PEDOT/PSS。Another useful hole transport material is the polycyclic aromatic compound described in EP 1 009 041. In addition, polymeric hole transport materials can also be used, such as poly(N-vinylcarbazole) (PVK). , polythiophene, polypyrrole, poly Aniline and copolymerized polymers such as poly(3,4-extended ethyldioxythiophene)/poly(4-styrene-sulfonate) are also known as PEDOT/PSS.

電子傳輸層(Elctron-transporting layer,ETL)Electron transport layer (ETL)

在此發明中,較合適之有機EL元件的電子傳輸層的薄膜材料為金屬螯合8-羥基喹啉類(oxinoid)化合物,包含8-羥基喹啉(oxine)螯合基(一般涉及如8-喹醇或8-羥基喹啉);此類的化合物可幫助電子的注入和傳輸及產生高效率和易於製作的薄膜型態;較為重要的8-羥基喹啉類化合物為符合上述之分子結構式(E)的化合物。In the invention, the film material of the electron transport layer of a suitable organic EL element is a metal chelate 8-oxoquinoline (oxinoid) compound comprising an 8-oxoquine chelating group (generally related to 8 - quinolol or 8-hydroxyquinoline); such compounds can aid in the injection and transport of electrons and produce a film pattern of high efficiency and ease of fabrication; the more important 8-hydroxyquinoline compound is in accordance with the above molecular structure a compound of formula (E).

其他可作為電子傳輸材料包含U.S.Pat.No.4,356,429所揭露之各種丁二烯衍生物及U.S.Pat.No.4,539,507所描述之各種雜環光學明亮劑(heterocyclic optical brighteners),而符合分子結構式(G)的苯并氮雜茂類也可作為可用的電子傳輸材料。Other various butadiene derivatives disclosed in US Pat. No. 4,356,429 and the various heterocyclic optical brighteners described in US Pat. No. 4,539,507, which are incorporated herein by reference. The benzazepines of G) are also useful as electron transport materials.

在某些例子中,發光層和電子傳輸層可選擇性的合併成單一層,亦即可同時兼顧發光和電子傳輸。In some instances, the luminescent layer and the electron transport layer can be selectively combined into a single layer, which can simultaneously accommodate both luminescence and electron transport.

陰極(Cathode)Cathode

如果設計為電激發光由陽極透出,則在此發明中幾乎任何可導電的材料皆可組成陰極,其中較為需求的材料特性為成膜性佳,此可確保陰極和底下的有機層有良好的接觸,進而提昇電子在低電壓時的注入,且要有好的穩定性;有用的陰極材料通常為低功函數的金屬(<4.0 eV)或金屬合金;U.S.Pat.No.4,885,221中所描述的鎂銀合金(Mg:Ag)為合適的陰極材料之一,其中銀的比率為1到20%;另一 種合適的陰極材料為包含一厚導電金屬層覆蓋一低功函數金屬薄層或金屬鹽之雙層式結構,U.S.Pat.No.5,677,572中所描述的此種陰極由一LiF薄層和一Al厚層所組成;其他有用的陰極材料包含但不限制於U.S.Pat.Nos.5,059,861、5,059,862和6,140,763中所被揭露的材料。If the electroluminescent light is designed to be permeable from the anode, almost any electrically conductive material in the invention can form a cathode, wherein the more desirable material property is good film formation, which ensures that the cathode and the underlying organic layer are good. Contact, which in turn enhances the injection of electrons at low voltages, and has good stability; useful cathode materials are typically low work function metals (<4.0 eV) or metal alloys; described in US Pat. No. 4,885,221 Magnesium-silver alloy (Mg: Ag) is one of the suitable cathode materials, wherein the ratio of silver is 1 to 20%; A suitable cathode material is a two-layer structure comprising a thick conductive metal layer covering a low work function metal thin layer or a metal salt. The cathode described in US Pat. No. 5,677,572 is a thin layer of LiF and an Al. Other useful cathode materials include, but are not limited to, the materials disclosed in US Pat. Nos. 5,059,861, 5,059,862 and 6,140,763.

而當元件設計為電激發光是透過陰極發出的話,則陰極必須為透明或接近於透明,在這種情況下,金屬必須很薄或必須使用透明的導電氧化物,或這些材料的組合;U.S.Pat.No.5,776,623中有關於光學透明陰極的詳細描述;沈積陰極材料的方法可為蒸鍍(evaporation)、濺鍍(sputtering)或化學氣相沈積(chemical vapor deposition),而必要時,陰極可被圖案化(patterning),經由許多熟知的方式,包含,但不限制於:經由遮罩沈積(through-mask deposition)、如U.S.Pat.No.5,276,380和EP 0 732 868所描述的整體蔭罩技術(integral shadow masking)、雷射燒蝕(laser ablation)和選擇性化學氣相沈積。When the component is designed to emit light through the cathode, the cathode must be transparent or nearly transparent. In this case, the metal must be thin or a transparent conductive oxide must be used, or a combination of these materials; US A detailed description of an optically transparent cathode is provided in Pat. No. 5,776,623; the method of depositing the cathode material may be evaporation, sputtering, or chemical vapor deposition, and if necessary, the cathode may be Patterning, in many well known ways, including, but not limited to, through-mask deposition, integral mask technology as described in US Pat. No. 5,276,380 and EP 0 732 868. (integral shadow masking), laser ablation and selective chemical vapor deposition.

此外,為了改善有機電激發光裝置的發光顏色、發光效率、發光穩定性、元件壽命與元件製作方式等,可參閱已頒予之美國專利案第4,356,429號、第4,539,507號、第4,720,432號、第4,885,211號、第5,151,629號、第5,150,006號、第5,141,671號、第5,073,446號、第5,061,569號、第5,059,862號、第5,059,861號、第5,047,687號、第4,950,950號、第4,769,292號、第5,104,740號、第5,227,252號、第5,256,945號、第5,069,975號、第5,122,711號、第5,366,811號、第5,126,214號、第5,142,343號、第5,389,444號、第 5,458,977號等。In addition, in order to improve the illuminating color, illuminating efficiency, illuminating stability, component life, and component manufacturing method of the organic electroluminescent device, reference is made to the issued U.S. Patent Nos. 4,356,429, 4,539,507, 4,720,432, 4,885,211, 5,151,629, 5,150,006, 5,141,671, 5,073,446, 5,061,569, 5,059,862, 5,059,861, 5,047,687, 4,950,950, 4,769,292, 5,104,740, 5,227,252 , 5, 256, 945, 5, 069, 975, 5, 122, 711, 5, 366, 811, 5, 126, 214, 5, 142, 343, 5, 389, 444, 5,458,977 and so on.

於本發明之具體實施例中,該有機電激發光裝置係一顯示器。一般而言,該顯示器可用於電視、行動電話、電腦顯示器、監視器、各式個人、家庭、辦公室及/或交通工具所使用之裝置及/或電器用品或其他可使用顯示器之裝置及/或電器用品。In a specific embodiment of the invention, the organic electroluminescent device is a display. In general, the display can be used in televisions, mobile phones, computer monitors, monitors, devices and/or electrical appliances or other devices that can use displays and/or devices used in various individuals, homes, offices, and/or vehicles. Electrical appliances.

以下為本發明實施方法:氧化銦錫(ITO)/電洞注入層(HIL)/電洞傳輸層(HTL)/綠光發光層(EML)/電子傳輸層(ETL)/電子注入層(EIL)/鋁(Al)(單位:奈米nm)。請參照第一圖之裝置截面圖。The following is a method for carrying out the invention: indium tin oxide (ITO) / hole injection layer (HIL) / hole transport layer (HTL) / green light emitting layer (EML) / electron transport layer (ETL) / electron injection layer (EIL) ) / aluminum (Al) (unit: nano nm). Please refer to the sectional view of the device in the first figure.

真空薄膜蒸鍍機(coater)係以TRC之18吋旋轉式蒸鍍機,其可放置9個擋板、8個電熱坩堝、5個震盪感應器、IC-5膜厚控制儀及擴散式幫浦。The vacuum film evaporator (coater) is a TRC 18-inch rotary evaporator, which can hold 9 baffles, 8 electric enthalpy, 5 oscillating sensors, IC-5 film thickness controller and diffusion gang Pu.

分光光度計(colorimeter)係使用PhotoResearch PR-650儀器進行量測。A spectrophotometer (colorimeter) was measured using a PhotoResearch PR-650 instrument.

電源供應器(programmable power supply)係使用KEITHLEY 2400儀器供給電流。A programmable power supply supplies current using a KEITHLEY 2400 instrument.

其製作程序如下:首先,依序使用去離子水,異丙醇超音波清洗(ultrasonic washing)透明電極氧化銦錫(ITO),然後再經紫外線(產生臭氧)照射10分鐘。將被清潔後的玻璃基板移進真空氣相沉積設備。當真空氣相沉積設備的真空度達到10-6 托耳(TORR)時開始操作。The production procedure was as follows: First, deionized water, ultrasonic washing, transparent electrode, indium tin oxide (ITO), and then ultraviolet (oxygen) irradiation for 10 minutes were used. The cleaned glass substrate is moved into a vacuum vapor deposition apparatus. The operation begins when the vacuum of the vacuum vapor deposition apparatus reaches 10 -6 Torr (TORR).

在有透明電極的表面上,形成一層薄膜S707具有厚度為100 nm,使形成的薄膜蓋透明電極。S707所形成的薄膜作為第一電洞注入層(電洞傳輸層)。然後在S707上形成20 nm的N,N’-雙(a-萘基)-N,N’-聯苯-4,4’-聯氨(NPB)。所形成的薄膜為第二個電洞注入層(電洞傳輸層)。On the surface having the transparent electrode, a film S707 was formed to have a thickness of 100 nm, so that the formed film cover was transparent. The film formed by S707 serves as a first hole injection layer (hole transport layer). Then, 20 nm of N,N'-bis(a-naphthyl)-N,N'-biphenyl-4,4'- hydrazine (NPB) was formed on S707. The formed film is a second hole injection layer (hole transport layer).

將式I化合物和MADN混合真空氣相沉積,形成厚度30 nm的發光層。The compound of formula I and MADN were mixed by vacuum vapor deposition to form a luminescent layer having a thickness of 30 nm.

再以8-羥基喹啉鋁(Alq)形成一厚度為10 nm薄膜作為電子注入層。之後,將氟化鋰(LiF)沉積在Alq上,作為電子注入層(陰極)。最後將金屬鋁以氣相沉積形成金屬陰極,以構成一綠光有機發光二極體。Further, a film having a thickness of 10 nm was formed as an electron injecting layer by 8-hydroxyquinoline aluminum (Alq). Thereafter, lithium fluoride (LiF) was deposited on Alq as an electron injection layer (cathode). Finally, the metal aluminum is vapor deposited to form a metal cathode to form a green organic light emitting diode.

實施例一:Embodiment 1:

(a)ITO(銦錫氧化物)玻璃基板40 mm x 40 mm厚1.1 mm,在甲醇中經由超音波清洗12分鐘,然後再經紫外線(產生臭氧)照射10分鐘。將被清潔後的玻璃基板移進真空氣相沉積設備。(a) ITO (Indium Tin Oxide) glass substrate 40 mm x 40 mm thick 1.1 mm, ultrasonically cleaned in methanol for 12 minutes, and then irradiated with ultraviolet rays (to produce ozone) for 10 minutes. The cleaned glass substrate is moved into a vacuum vapor deposition apparatus.

(b)在有透明電極的表面上,形成一層薄膜S707具有厚度為75 nm,使形成的薄膜蓋透明電極。所形成的薄膜S707作為第一電洞注入層(電洞傳輸層)。(b) On the surface having the transparent electrode, a film S707 was formed to have a thickness of 75 nm, so that the formed film cover was transparent. The formed thin film S707 serves as a first hole injection layer (hole transport layer).

(c)然後在S707上形成15 nm的NPB。所形成的薄膜為第二個電洞注入層(電洞傳輸層)。(c) A 15 nm NPB was then formed on S707. The formed film is a second hole injection layer (hole transport layer).

(d)將化合物E502和MADN混合真空氣相沉積,形成厚度30 nm的MADN和含7%的E502,作為發光層。(d) Compound E502 and MADN were mixed by vacuum vapor deposition to form MADN having a thickness of 30 nm and E502 containing 7% as a light-emitting layer.

(e)再以Alq形成一厚度為25 nm薄膜作為電子注入層。(e) A film having a thickness of 25 nm was formed as an electron injecting layer by Alq.

(f)將氟化鋰(LiF)沉積在Alq上,作為電子注入層(陰極)。(f) Lithium fluoride (LiF) was deposited on Alq as an electron injecting layer (cathode).

(g)最後將金屬鋁以氣相沉積形成金屬陰極,製成有機電激發光二極體。(g) Finally, metal aluminum is vapor-deposited to form a metal cathode to form an organic electroluminescent diode.

(h)將以上製成的元件經過電流並利用光色計量測其亮度(luminance)和發光效率(luminance efficiency)。(h) The element fabricated above is subjected to a current and its luminance and luminance efficiency are measured by light color.

在電流密度20mA/cm2 驅動有機電激發光二極體時,驅動電壓為5.69 V,發出綠光、CIE(0.289,0.644)發光亮度為4026.28 cd/m2 ,發光效率20.13 cd/A。When the organic electroluminescence photodiode was driven at a current density of 20 mA/cm 2 , the driving voltage was 5.69 V, and green light was emitted, and the luminance of CIE (0.289, 0.644) was 4026.26 cd/m 2 , and the luminous efficiency was 20.13 cd/A.

實施例二:Embodiment 2:

有機電激發光二極體製作,依照實施例一的程序,以厚度30 nm的MADN和含3%的E505,作為發光層。The organic electroluminescent diode was fabricated, and according to the procedure of Example 1, MADN having a thickness of 30 nm and E505 containing 3% were used as the light-emitting layer.

以電流密度20mA/cm2 驅動有機電激發光二極體時,驅動電壓為6.95 V,發出綠光、CIE(0.306,0.634)發光亮度為2802.27 cd/m2 ,發光效率14.01 cd/A。When the organic electroluminescence diode was driven at a current density of 20 mA/cm 2 , the driving voltage was 6.95 V, and green light was emitted, and the luminance of CIE (0.306, 0.634) was 2802.27 cd/m 2 , and the luminous efficiency was 14.01 cd/A.

實施例三:Embodiment 3:

有機電激發光二極體製作,依照實施例一的程序,以厚度30 nm的MADN和含5%的E506,作為發光層。The organic electroluminescent diode was fabricated, and according to the procedure of Example 1, MADN having a thickness of 30 nm and E506 containing 5% were used as the light-emitting layer.

以電流密度20mA/cm2 驅動有機電激發光二極體時, 驅動電壓為6.05 V,發出綠光、CIE(0.314,0.633)發光亮度為4533.58 cd/m2 ,發光效率22.66 cd/A。When the organic electroluminescent diode was driven at a current density of 20 mA/cm 2 , the driving voltage was 6.05 V, and green light was emitted, and the luminance of CIE (0.314, 0.633) was 4533.58 cd/m 2 , and the luminous efficiency was 22.66 cd/A.

實施例四:Embodiment 4:

有機電激發光二極體製作,依照實施例二的程序,以厚度37.5 nm的MADN和含12%的E507,作為發光層。The organic electroluminescent diode was fabricated. According to the procedure of the second embodiment, MADN having a thickness of 37.5 nm and E507 having a thickness of 12% were used as the light-emitting layer.

以電流密度20mA/cm2 驅動有機電激發光二極體時,驅動電壓為8.02 V,發出藍綠光、CIE(0.344,0.613)發光亮度為3337.96 cd/m2 ,發光效率16.69 cd/A。When the organic electroluminescence diode was driven at a current density of 20 mA/cm 2 , the driving voltage was 8.02 V, and blue-green light, CIE (0.344, 0.613) luminance was 3337.96 cd/m 2 , and the luminous efficiency was 16.69 cd/A.

實施例五:Embodiment 5:

有機電激發光二極體製作,依照實施例一的程序,以厚度30 nm的MADN和含3%的E512,作為發光層。The organic electroluminescent diode was fabricated. According to the procedure of Example 1, MADN having a thickness of 30 nm and E512 containing 3% were used as the light-emitting layer.

以電流密度20mA/cm2 驅動有機電激發光二極體時,驅動電壓為6.58 V,發出綠光、CIE(0.353,0.620)發光亮度為4567.88 cd/m2 ,發光效率22.83 cd/A。When the organic electroluminescence diode was driven at a current density of 20 mA/cm 2 , the driving voltage was 6.58 V, and green light was emitted. The luminance of CIE (0.353, 0.620) was 4567.78 cd/m 2 and the luminous efficiency was 22.83 cd/A.

比較例:Comparative example:

ITO(銦錫氧化物)玻璃基板40 mm x 40 mm厚1.1 mm,在甲醇中經由超音波清洗12分鐘,然後再經紫外線(產生臭氧)照射10分鐘。將被清潔後的玻璃基板移進真空氣 相沉積設備。在有透明電極的表面上,形成一層薄膜S707具有厚度為100 nm,使形成的薄膜蓋透明電極。所形成的薄膜S707作為第一電洞注入層(電洞傳輸層)。然後在S707上形成20 nm的NPB。所形成的薄膜為第二個電洞注入層(電洞傳輸層)。將化合物C545T和MADN混合真空氣相沉積,形成厚度30 nm的MADN和含1%的C545T,作為發光層。再以Alq形成一厚度為15 nm薄膜作為電子注入層。之後,將氟化鋰(LiF)沉積在Alq上,作為電子注入層(陰極)。最後將金屬鋁以氣相沉積形成金屬陰極,就做好了有機電激發光二極體。The ITO (Indium Tin Oxide) glass substrate was 40 mm x 40 mm thick and 1.1 mm thick, ultrasonically cleaned in methanol for 12 minutes, and then irradiated with ultraviolet rays (to produce ozone) for 10 minutes. Move the cleaned glass substrate into the vacuum gas Phase deposition equipment. On the surface having the transparent electrode, a film S707 was formed to have a thickness of 100 nm, so that the formed film cover was transparent. The formed thin film S707 serves as a first hole injection layer (hole transport layer). A 20 nm NPB was then formed on S707. The formed film is a second hole injection layer (hole transport layer). Compound C545T and MADN were mixed by vacuum vapor deposition to form MADN having a thickness of 30 nm and C545T containing 1% as a light-emitting layer. A film having a thickness of 15 nm was formed as an electron injecting layer by Alq. Thereafter, lithium fluoride (LiF) was deposited on Alq as an electron injection layer (cathode). Finally, the metal aluminum is vapor deposited to form a metal cathode, and the organic electroluminescent diode is prepared.

以電流密度20mA/cm2 驅動有機電激發光二極體時,驅動電壓為8.28 V,發出藍綠光、CIE(0.254,0.613)發光亮度為2885.40 cd/m2 ,發光效率14.42 cd/A。When the organic electroluminescence diode was driven at a current density of 20 mA/cm 2 , the driving voltage was 8.28 V, and blue-green light, CIE (0.254, 0.613) luminance of 2885.40 cd/m 2 , and luminous efficiency of 14.42 cd/A were emitted.

從表一、表二及表三中,此系列化合物與C545T製作成元件後,與C545T比較,E502可降低驅動電壓2.59V,並增加約40%的發光效率;E506可降低驅動電壓2.23V,並增加約57%的發光效率;E507可降低驅動電壓0.26V,並增加約16%的發光效率;E512可降低驅動電壓1.7V,並增加約58%的發光效率。在操作穩定性方面,C545T在發光亮度4000cd/m2 下定電流驅動,元件壽命(t1/2 )為1770小時;E506在相同條件下操作,元件壽命(t1/2 )增加4.46倍達7900小時。明顯發現以本發明之綠光有機化合物摻雜於 一適當主體發光材料中,其有機電激發光元件裝置可得到一具有高發光效率,飽和色純度和長操作穩定性之綠光元件。本發明以詳述具體實例,任何可想到之相關衍生物將會涵蓋於本發明的精神與範圍。From Table 1, Table 2 and Table 3, after the series of compounds and C545T are fabricated into components, compared with C545T, E502 can reduce the driving voltage by 2.59V and increase the luminous efficiency by about 40%; E506 can reduce the driving voltage by 2.23V. And increase the luminous efficiency by about 57%; E507 can reduce the driving voltage by 0.26V and increase the luminous efficiency by about 16%; E512 can reduce the driving voltage by 1.7V and increase the luminous efficiency by about 58%. In terms of operational stability, the C545T is driven at a constant current of 4000 cd/m 2 with a component lifetime (t 1/2 ) of 1770 hours; the E506 operates under the same conditions, and the component lifetime (t 1/2 ) increases by 4.46 times to 7900. hour. It is apparent that the green organic compound of the present invention is doped into a suitable host luminescent material, and the organic electroluminescent device thereof can obtain a green light element having high luminous efficiency, saturated color purity and long operational stability. The present invention is intended to be illustrative of specific examples, and any conceivable related derivatives are intended to cover the spirit and scope of the invention.

10‧‧‧有機電激發光裝置10‧‧‧Organic electroluminescent device

11‧‧‧玻璃基板11‧‧‧ glass substrate

12‧‧‧陽極12‧‧‧Anode

13‧‧‧電洞注入層13‧‧‧ hole injection layer

14‧‧‧電洞傳輸層14‧‧‧ hole transport layer

15‧‧‧發光層15‧‧‧Lighting layer

16‧‧‧電子傳輸層16‧‧‧Electronic transport layer

17‧‧‧電子注入層17‧‧‧Electronic injection layer

18‧‧‧金屬陰極18‧‧‧Metal cathode

19‧‧‧電源19‧‧‧Power supply

第一圖為一般有機電激發光裝置之結構示意圖。The first figure is a schematic structural view of a general organic electroluminescent device.

10‧‧‧有機電激發光裝置10‧‧‧Organic electroluminescent device

11‧‧‧玻璃基板11‧‧‧ glass substrate

12‧‧‧陽極12‧‧‧Anode

13‧‧‧電洞注入層13‧‧‧ hole injection layer

14‧‧‧電洞傳輸層14‧‧‧ hole transport layer

15‧‧‧發光層15‧‧‧Lighting layer

16‧‧‧電子傳輸層16‧‧‧Electronic transport layer

17‧‧‧電子注入層17‧‧‧Electronic injection layer

18‧‧‧金屬陰極18‧‧‧Metal cathode

19‧‧‧電源19‧‧‧Power supply

Claims (8)

一種使用2-甲基蒽化合物之有機電激發光裝置,至少包含有:陰極、陽極以及其間之有機層,其中該有機層包括有一電洞注入層、一電洞傳輸層、一發光層、一電子傳輸層、一電子注入層,其中至少一層發光層含有主發光體材料以及客發光體材料,該主發光體材料係為蒽類化合物及其衍生物,而該客發光體材料為0.01至小於50%重量比之下式I化合物: 其中,Y1 ,Y2 ,Y3 和Y4 係代表相同或不同之選擇性經C1 -C6 烴基取代之C6 ~C20 芳基基團。An organic electroluminescent device using a 2-methylindole compound, comprising at least a cathode, an anode and an organic layer therebetween, wherein the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, and a An electron transport layer, an electron injection layer, wherein at least one of the light-emitting layers comprises a main illuminant material and a guest illuminant material, wherein the main illuminant material is a quinone compound and a derivative thereof, and the guest illuminant material is 0.01 to less than 50% by weight of the compound of formula I: Wherein Y 1 , Y 2 , Y 3 and Y 4 represent the same or different C 6 -C 20 aryl groups optionally substituted by a C 1 -C 6 hydrocarbon group. 如申請專利範圍第1項所述之使用2-甲基蒽化合物之有機電激發光裝置,其中,該主發光體材料係選自於MADN及其衍生物 An organic electroluminescent device using a 2-methylindole compound according to claim 1, wherein the main emitter material is selected from the group consisting of MADN and its derivatives. 如申請專利範圍第1或2項所述之使用2-甲基蒽化合物之有機電激發光裝置,其中該客發光體材料為0.5至20%重量比之式I化合物。 An organic electroluminescent device using a 2-methylindole compound as described in claim 1 or 2, wherein the guest emitter material is from 0.5 to 20% by weight of the compound of formula I. 如申請專利範圍第1或2項所述之使用2-甲基蒽化合物之有機電激發光裝置,其中,該有機電激發光裝置放射出綠色的光。 An organic electroluminescent device using a 2-methylindole compound according to claim 1 or 2, wherein the organic electroluminescent device emits green light. 如申請專利範圍第1或2項所述之使用2-甲基蒽化合物之有機電激發光裝置,其中,各有機層的總厚度小於500nm。 An organic electroluminescent device using a 2-methylindole compound according to claim 1 or 2, wherein the total thickness of each organic layer is less than 500 nm. 如申請專利範圍第1或2項所述之使用2-甲基蒽化合物之有機電激發光裝置,該經C1 -C6 烴基取代與非取代之芳香族為苯基、2-甲苯基、3-甲苯基、4-甲苯基、3,4-二甲苯基、萘基或蒽基。An organic electroluminescent device using a 2-methylindole compound according to claim 1 or 2, wherein the C 1 -C 6 hydrocarbon group-substituted and unsubstituted aromatic group is a phenyl group, a 2-tolyl group, 3-tolyl, 4-tolyl, 3,4-dimethylphenyl, naphthyl or anthracenyl. 如申請專利範圍第1或2項所述之使用2-甲基蒽化合物之有機電激發光裝置,該客發光體材料可選自下列化合物:,或,或,或,或,或,或,或,或,或,或,或,或 An organic electroluminescent device using a 2-methylindole compound as described in claim 1 or 2, the guest emitter material may be selected from the following compounds: ,or ,or ,or ,or ,or ,or ,or ,or ,or ,or ,or ,or 如專利申請範圍第1或2項所述之使用2-甲基蒽化合物之有機電激發光裝置,其中該式I化合物係選自於由 所構成的群組中,以及其中該發光主體係選自於 An organic electroluminescent device using a 2-methylindole compound as described in claim 1 or 2, wherein the compound of formula I is selected from the group consisting of In the group formed, and wherein the main system of illumination is selected from
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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1146034A1 (en) * 1995-09-25 2001-10-17 Toyo Ink Manufacturing Co., Ltd. Light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1146034A1 (en) * 1995-09-25 2001-10-17 Toyo Ink Manufacturing Co., Ltd. Light-emitting material for organic electroluminescence device, and organic electroluminescence device for which the light-emitting material is adapted

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