CN1674746A - 有机电致发光器件 - Google Patents
有机电致发光器件 Download PDFInfo
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- CN1674746A CN1674746A CNA2005100557533A CN200510055753A CN1674746A CN 1674746 A CN1674746 A CN 1674746A CN A2005100557533 A CNA2005100557533 A CN A2005100557533A CN 200510055753 A CN200510055753 A CN 200510055753A CN 1674746 A CN1674746 A CN 1674746A
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 23
- 238000002347 injection Methods 0.000 claims abstract description 19
- 239000007924 injection Substances 0.000 claims abstract description 19
- -1 heterocyclic radical Chemical class 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 5
- 230000004888 barrier function Effects 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000005540 biological transmission Effects 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 239000010405 anode material Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- AFXPGBCYVXWKDB-UHFFFAOYSA-N O[BrH](=O)(=O)C1=CC=CC=C1 Chemical compound O[BrH](=O)(=O)C1=CC=CC=C1 AFXPGBCYVXWKDB-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000004456 color vision Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03B—INSTALLATIONS OR METHODS FOR OBTAINING, COLLECTING, OR DISTRIBUTING WATER
- E03B5/00—Use of pumping plants or installations; Layouts thereof
- E03B5/04—Use of pumping plants or installations; Layouts thereof arranged in wells
- E03B5/06—Special equipment, e.g. well seals and connections for well casings or the like
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- E—FIXED CONSTRUCTIONS
- E03—WATER SUPPLY; SEWERAGE
- E03B—INSTALLATIONS OR METHODS FOR OBTAINING, COLLECTING, OR DISTRIBUTING WATER
- E03B3/00—Methods or installations for obtaining or collecting drinking water or tap water
- E03B3/06—Methods or installations for obtaining or collecting drinking water or tap water from underground
- E03B3/08—Obtaining and confining water by means of wells
- E03B3/15—Keeping wells in good condition, e.g. by cleaning, repairing, regenerating; Maintaining or enlarging the capacity of wells or water-bearing layers
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- E03—WATER SUPPLY; SEWERAGE
- E03B—INSTALLATIONS OR METHODS FOR OBTAINING, COLLECTING, OR DISTRIBUTING WATER
- E03B3/00—Methods or installations for obtaining or collecting drinking water or tap water
- E03B3/06—Methods or installations for obtaining or collecting drinking water or tap water from underground
- E03B3/08—Obtaining and confining water by means of wells
- E03B3/16—Component parts of wells
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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Abstract
本发明提供了一种有机电致发光器件,通过该器件以使用降低能垒的材料形成空穴注入或传输层的方式提供高亮度。本发明包括阴极与阳极之间的有机发射层和阳极与有机发射层之间的空穴注入和/或传输层,其中至少空穴注入和传输层之一具有化学式1的结构。
Description
本申请要求2004年3月22日提交的韩国申请No.10-2004-19357为优先权,并在此将其作为参考。
技术领域
本发明涉及一种在阴极和阳极之间包括空穴注入或传输层的有机电致发光器件。
背景技术
近来,随着制造宽屏显示器装置的趋势,对占据更少空间的平板显示器装置的需求正不断增加。
被称为有机光发射二极管(OLED)的有机电致发光器件技术作为平板显示器装置的一种已被快速地发展起来。并且已经发布了各种原型机。
有机电致发光器件是一种以以下方式发光的装置。首先,如果电荷被注入阴极和阳极之间的有机层,则电子和空穴对形成并湮灭。在湮灭的同时,电子/空穴对发射光。
因此,可以在如塑料的柔性透明基质上形成的有机电致发光器件可以在低于等离子显示板(PDP)或无机电致发光(EL)显示器的电压下(低于10V)被驱动。
有机电致发光器件只需要相对低的电能消耗并提供极佳的色彩感觉。
为了在低电压下驱动有机电致发光器件,重要的是保持有机层非常薄且均一的厚度(100~200nm)以及装置的稳定性。
为了对有机电致发光器件提供高效率,重要的是保持空穴和电子之间的密度平衡。
例如,如果电子传输层(ETL)位于发射层(EML)和阴极之间,大部分从阴极注入发射层的电子会向阳极移动以与空穴结合。
但是,如果在阳极和发射层之间插入空穴传输层(HTL),注入发射层的电子被空穴传输层的界面阻隔。如此以来,电子不能继续向阳极移动而仅滞留在发射层中。因此,提高了结合效率。
同时,空穴注入层(HIL)被另外地插入阳极和空穴传输层之间。
如果考虑阳极的功函数(4.7~5.0eV)和空穴传输层的电离电位(IP)而选择具有5.0~5.2eV功函数的有机物质,则降低了在从阳极到空穴传输层的空穴注入能垒,从而能够高效地注入空穴。
制备有机EL器件的过程说明如下。
(1)首先,阳极材料被覆盖在透明基质上。ITO(氧化铟锡)通常被用作阳极材料。
(2)空穴注入层(HIL)被覆盖在阳极材料上。铜酞青(CuPC)作为空穴注入层被大体上以10~30nm厚度覆盖其上。
(3)引入空穴传输层(HTL)。4,4′-二[N-(1-萘基)-N-苯氨基]联苯(4,4’-bis[N-(1-naphthyl)-N-phenthylamino]-biphenyl)(NPB)作为空穴传输层以30~60nm厚度被沉积。
(4)在其上形成有机发射层。在此过程中,如果需要则向其中添加掺杂剂。为了发射绿光,Alq3(三(8-羟基-喹啉铝))(tris(8-hydroxy-quinolatealuminum))作为有机发射层以30~60nm厚度被沉积。并且MQD(N-甲基喹吖啶酮)主要被用作掺杂剂。
(5)在其上连续地覆盖电子传输层(ETL)和电子注入层(EIL)或者形成电子注入传输层。如果发射绿光,电子注入/传输层并不经常使用,因为(4)中的Alq3具有足够的电子传输能力。
(6)在其上覆盖阴极。并且,在其上最后形成保护层。
然而,现有技术的器件需要降低空穴注入能垒的材料以有效地注入空穴。
发明内容
因此,本发明致力于一种充分地避免由现有技术的限制和缺点造成的一个或多个问题的有机电致发光器件。
本发明的一个目的是提供一种有机电致发光器件,通过该器件以使用降低能垒的材料形成空穴注入或传输层的方式提供高亮度。
本发明的其它的优点、目的和特性在下面的说明中被部分地阐明并且本领域普通技术人员通过对下面的说明的考查将变得很清楚或者可以从本发明的实施中理解。本发明的目的和其它优点可通过所撰写的说明书和权利要求书以及附图中特别指出的结构而实现和达到。
为了达到这些目的和其它优点并与本发明的宗旨相一致,如其中具体和宽泛地描述,根据本发明的有机电致发光器件包括在阴极与阳极之间的有机发射层和在阳极与有机发射层之间的空穴注入和/或传输层,其中至少空穴注入和传输层之一具有化学式1的结构。
[化学式1]
其中R1至R6中的每一个选自独立地取代或未取代的芳香基、杂环基、脂族基和氢。
可以理解对本发明的前面一般性描述和随后详细描述均是范例性和解释性的并对所要求的发明提供进一步的解释。
具体实施方式
现将对本发明的优选实施例进行详细描述。
根据本发明的有机电致发光器件可以通过顺序地叠加阳极、空穴注入层、空穴传输层、有机发射层、电子传输层、电子注入层和阴极而形成。
其中,至少空穴注入和传输层之一可以由具有化学式1的结构的材料形成。
[化学式1]
在化学式1中,R1至R6中的每一个可以选自独立地取代或未取代的芳香基、杂环基、脂族基和氢。
具体地,R1至R6中的每一个可以选自取代或未取代的苯基、联苯基、吡啶基、萘基、喹啉基、异喹啉基、芴基、三联苯基、蒽基、菲基、甲基、乙基、丙基、i-丙基、t-丁基和氢。
另外,R1至R6的每一个取代功能团可以选自包含烷基、芳基、烷氧基、卤素、氰基等的组。
例如,R1至R6的每一个取代功能团可以选自包含甲基、乙基、丙基、i-丙基、t-丁基、环己基、甲氧基、乙氧基、丙氧基、丁氧基、苯氧基、甲苯氧基、F、Cl和氰基的组。
另外,空穴注入或传输层可以具有下面化学式2所示的结构。
[化学式2]
在根据本发明的有机电致发光器件中,以下面方式合成被用作空穴注入或传输层的N3,N4’-二-萘-1-基-N3,N5,N5,N4’-四苯基-二苯基-3,5,4’-三胺(HM-03)。
1、(3’,5’-二溴-联苯-4-基)-萘-1-基-苯基-胺的合成。
首先,在两颈圆底烧瓶中,将1,3,5-三溴苯(14.8g,0.047mol)、4-(N-萘-1-基-N-苯氨基)苯基溴酸(4g,0.012mol)、四(三苯基膦基)钯(0.7g,0.0006mol)和K2CO3(碳酸钾)(4.15g,0.03mol)溶解于甲苯(150mL)、THF(150mL)和水(80mL)中,且然后在100℃振摇24小时。
一旦反应终止后,进行真空蒸馏以除去THF和甲苯。并且,使用二氯甲烷进行萃取。
接着,使用二氯甲烷和甲醇对萃取的溶液进行重结晶。然后进行过滤以获得白色固体产物3’,5’-二溴-联苯-4-基-萘-1-基-苯基-胺(4.77g,76%)。
2、N3,N4’-二-萘-1-基-N3,N5,N5,N4’-四苯基-二苯基-3,5,4’-三胺(HM-03)的合成。
在两颈圆底烧瓶中,将3’,5’-二溴-联苯-4-基-萘-1-基-苯胺(4.7g,0.0089mol)、萘-1-基-苯胺(5.84g,0.027mol)、BINAP(2,2’-二(联苯膦基)-1,1’-联萘)(0.221g,0.36mol)、Pd(OAc)2(醋酸钯)(0.059g,0.26mmol)和NaOtBu(叔丁醇钠)(3.84g,0.04mol)溶于甲苯(100mL)中并随后在100℃搅拌24小时。
一旦反应终止后,进行真空蒸馏以除去甲苯。并且,使用甲苯和甲醇进行重结晶。然后过滤以获得HM-03的白色固体产物(5.08g,71%)。
根据本发明的优选实施例的有机电致发光器件加以解释如下。
实施例
ITO(氧化铟锡)基质(玻璃)被形成图案以具有3mm×3mm的发射尺寸。并且,对形成图案的基质进行清洁处理。
随后,当基质被装入真空室后,基中保持1×10-6torr的基本压力。并且,以空穴注入层(600)、空穴传输层(400)、发射层(200)、Alq3(400)、LiF(5)和Al(1000)的顺序在ITO基质上形成有机物质层。
实施例1
HM-03和NPB被分别用作空穴注入和传输层。如果施加1mA的电流,驱动电压为10.6V且亮度为2320cd/m2。如此以来,CIE(CommisionInternationale de L’Eclairage)为x=0.329和y=0.627。
实施例2
CuPc和HM-03被分别用作空穴注入和传输层。如果施加1mA的电流,驱动电压为8.7V且亮度为2160cd/m2。如此以来,CIE为x=0.363和y=0.603。
对比实施例
CuPc和NPB被分别用作空穴注入和传输层。如果施加1mA的电流,驱动电压为8.5V且亮度为1541cd/m2。如此以来,CIE为x=0.351和y=0.612。CuPc、NPB和Alq3的化学式如化学式3所示。
[化学式3]
因此,根据本发明的有机电致发光器件包括至少在阳极与阴极之间的空穴注入和传输层之一。并且,空穴注入或传输层由具有如化学式1所示结构的物质形成。因而,通过本发明可以制备高亮度的有机电致发光器件。
可对本发明作出各种修改和变化,这对本领域技术人员是显而易见的。因此,本发明包括了落在附属权利要求和其等效范围内的本发明的修改和变化。
Claims (5)
2、根据权利要求1的有机电致发光器件,其特征在于,至少R1至R6中之一选自包含取代或未取代的苯基、联苯、吡啶基、萘基、喹啉基、异喹啉基、芴基、三联苯、蒽基、菲基、甲基、乙基、丙基、i-丙基、t-丁基和氢。
3、根据权利要求1的有机电致发光器件,其特征在于,R1至R6的各个取代功能团选自包含烷基、芳基、烷氧基、卤素和氰基的组。
4、根据权利要求3的有机电致发光器件,其特征在于,R1至R6的取代功能团选自包含甲基、乙基、丙基、i-丙基、t-丁基、环己基、甲氧基、乙氧基、丙氧基、丁氧基、苯氧基、甲苯氧基、F、Cl和氰基的组。
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CN115028539A (zh) * | 2021-03-03 | 2022-09-09 | 江苏三月科技股份有限公司 | 一种芳胺衍生物及使用该衍生物的有机电致发光器件 |
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