CN1534076A - 用于有机电致发光器件的发射红光的化合物和应用它们的有机电致发光器件 - Google Patents
用于有机电致发光器件的发射红光的化合物和应用它们的有机电致发光器件 Download PDFInfo
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- CN1534076A CN1534076A CNA2003101240235A CN200310124023A CN1534076A CN 1534076 A CN1534076 A CN 1534076A CN A2003101240235 A CNA2003101240235 A CN A2003101240235A CN 200310124023 A CN200310124023 A CN 200310124023A CN 1534076 A CN1534076 A CN 1534076A
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
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- 150000003852 triazoles Chemical class 0.000 description 1
- FNEGQWLLZQVLNI-UHFFFAOYSA-N triethoxy phosphate Chemical compound CCOOP(=O)(OOCC)OOCC FNEGQWLLZQVLNI-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及用于有机电致发光器件(OELD)的发射红光的化合物,特别涉及由下述式(1)表示的具有高发光效率和热稳定性提高的发射红色光的化合物:R1-CH=CH-X-CH=CH-R2其R1、R2和X各自如说明书和权利要求书定义。
Description
技术领域
本发明涉及用于有机电致发光器件(OELD)的发射红光的化合物,具体地说,涉及用下述式(1)表示的,具有高电致发光效率和提高了热稳定性的发射红光的化合物:
R1-CH=CH-X-CH=CH-R2
其中R1,R2和X各自如下文定义。
另外,本发明还涉及含有该发射红光化合物的有机电致发光器件,特别涉及具有一种或多种有机薄层的有机电致发光器件,所述有机薄层含有在第一电极和第二电极之间形成的发光区,其中在所述有机薄层中至少任意一层含有一种或多种上述式(1)表示的化合物。
背景技术
显示器装置领域在信息和通讯工业中是非常重要的。近年来随着信息和通讯技术的发展,这一领域需要有更高新的技术。显示器可分为发光型和非发光型。发光型的显示器包括阴极射线管(CRT)、电致发光显示器(ELD)、发光二极管(LED)、等离子体显示屏(PDP)等。非发光型显示器包括液晶显示器(LCD)等。
发光和非发光显示器的基本性能如操作电压、功耗、亮度、对比度、响应速度、寿命等。但是现在已广泛应用的LCD在响应速度、对比度和视觉依赖性的上述基本性能方面存在问题。因此,可以预期使用LCD的显示器会被新一代的显示器所替代,所述新一代的显示器可以解决上述LCD的问题,以及可提供许多其它的优点例如更快的响应速度,由于自身的发光不需要黑屏(back light),以及很好的亮度。
但是,LED主要是用晶体形式的无机材料,因此难以应用于大型的电致发光器件。此外,使用无机材料的电致发光器件很贵,并且需要大于200V的操作电压。但是,1987年Eastman Kodak报道了该公司用具有π-结构的材料如氧化铝奎宁制造的器件,对电致发光器件的上述研究使用了活性更高的有机材料。
根据形成发光层(发射层)所使用的材料,电致发光器件(下文称做EL器件)可分为无机EL器件和有机EL器件。
有机EL器件是自-发射型的器件,是通过电子激发荧光有机化合物,在亮度、操作电压和响应速度方面均优于无机EL器件,并且可以发射多色。
此外有机EL器件是在低电压电流下可以发光的器件,因此具有优良的性能如高亮度、高响应速度、宽视角、平面发光、微(slim)型和多色发光。
因此,由于上述在其它显示器中没有的优异性能,预期有机EL器件可应用于全色平板显示器。
C.W.Tang等人报道了有机EL器件的第一个实用的器件(AppliedPhysics Letters,vol.51(12)pp 913-915(1987))。他们研制了用二胺类似物作为有机层形成的层压结构薄膜(空穴传输层),和用三(8-喹啉醇化)铝(下文为Alq3)形成的薄膜(电子传输层)。层压结构可降低电子和空穴由二电极向有机层注射的屏障,也可提高电子和空穴由有机层的内层再结合的可能性。
在这之后,Later,C.Adachi等人研制了具有有机发光层的EL器件,该发光层具有空穴传输层、发射层和电子传输层的三层结构[Japanese Journal of Applied Physics,vol.27(2),pp L269-L271(1988)],和具有空穴传输层和电子传输层的二层结构[Applied Physics Letter,vol.55(15),pp 1489-1491(1989)],并指出最佳的器件性能可通过构建适用材料以及它们的结合的多层结构来实现。
有机EL包括第一电极(阳极)、第二电极(阴极)和有机发光介质。所述的有机发光介质具有至少二个分开的有机发光层,即一层向器件注射和传输电子,另一层向器件注射和传输空穴。另外也可包括其它多层有机薄膜。上述注射和传输电子和空穴的各层可分别划分为电子注射层、电子传输层、空穴注射层和空穴传输层。此外,除了上述各层之外,有机发光介质可进一步包括发射层。
有机EL器件的简单结构包括第一电极/电子传输层,和发射层/第二电极。另外,有机EL器件还可以分成第一电极/空穴注射层/空穴传输层/发射层/电子传输层/电子注射层/第二电极。
具有上述结构的有机EL器件的操作原理如下。
在阳极和阴极之间加上电压,由阳极注射的空穴通过空穴传输层被传输到发射层。与此同时,由阴极注射的电子通过电子传输层被传输到发射层。在发射层中空穴和电子结合形成激子。该激子由激发态变成基态,因此使发射层的荧光分子发光而形成图象。
常规的有机EL器件的制造方法参照下文图1进行说明。
首先,在透明基质如玻璃1上形成阳极材料2。在这种情况下,通常使用氧化铟锡(ITO:In2O3+SnO2)作为阳极材料2。在阳极材料2上可形成空穴注射层(HIL)3或空穴传输层(HTL)4,或依次形成HIL 3和HTL 4两者。
在这种情况下,通常使用0-30nm厚的铜(II)酞菁(CuPC)作为HIL3,和用30-60nm厚的N,N-二(萘-1-基)-N,N′-二苯基联苯胺(NPD)作为HTL 4。
然后,在HIL 3或HTL 4上形成有机发射层5。具体地,可以只使用发光材料作为发射层5,或在主体(host)材料中掺入少量偶然出现的杂质。例如,在发射绿光的情况下,通常使用大约30-60nm厚的三(8-喹啉醇化)铝(Alq3)作为主体,和以MQD(N-甲基喹吖啶酮)作为有机发射层5的掺杂剂。
其次,在发射层5上独立地形成,或依次形成电子传输层6或电子注射层7。Alq3通常以大约20-50nm的厚度用作电子传输层,碱金属类似物以大约30-50nm的厚度用作电子注射层。在发射绿光的情况下,由于用作有机发射层的Alq3具有良好的电子传输能力,因此可以不再使用电子传输层6或电子注射层7。
进一步地,第二电极(阴极)8在电子传输层6或电子注射层7上形成,最后形成保护层。
要实现全色有机EL器件,通常需要发绿色、红色和兰色的三种发光器件。
兰色通过在发兰色光的主体中掺入发射兰色的掺杂剂,并使用Alq3作为电子传输层来实现,根据兰色主体的性质,也可以不掺杂Alq3。在发红色光器件的情况下,在上述制造器件的过程中通过掺入发射红光的掺杂剂,而不是掺入发射绿光的掺杂剂而得到红色波长。
在发绿光器件的情况下,用香豆素6或喹吖啶酮类似物作为掺杂剂,和在发红光器件的情况下,使用DCM(4-二氰基亚甲基-6-(对二甲氨基苯乙烯基(stylyl))-2-甲基-4H-吡喃(pyrnae))类似物如DCM1或DCM2等作为掺杂剂[参见Journal of Applied Physics,3610(1989)]。
但是,在发绿光器件的情况下,经评价器件的安全性达到了实用的水平,而发红色光器件在发光的颜色和器件的安全性上还没有达到实用的水平。
这就是说,在红/绿/兰三种发光器件中,对发红光器件的最新研究还没有达到足够的亮度和色度。例如,上述DCM的发光光谱的峰波长在600nm,半带宽的宽度是大约100nm,因此,相应于全色,红色的色度大大偏低。此外,如果发射红光的掺杂剂如DCM的浓度小,就会得到橙色区域光谱;如果浓度大可发射出红色区域,但由于本身的淬灭发光效率降低。另外,使用掺杂了DCJTB[4-(二氰基亚甲基)-2-叔丁基-6-(四甲基julolidi-4-基)-4H-吡喃]的Alq3[三(8-喹啉醇化)铝]作为电子传输材料的发射红光的器件作为显示器材料在其亮度和色度上是不能令人满意的。
但是,已知其中心金属是铕的有机金属络合物是发射红光的物质,且具有高色度,但使用该物质的有机EL器件的最大亮度非常低[参见Applied Physics Letter,65(17),2124-2126(1994)]。
日本专利公开号1999-329731公开了通过使用特殊的二苯乙烯基化合物制造发射红光的有机EL器件,但是发光光谱的半带宽大于100nm,因此,其色度被认为是不完全的。
为了解决上述问题,本发明人进行了广泛的研究,研制了发射红光的材料,该材料在高亮度时是安全的,并且有很好的色度,从而完成了本发明。
发明概述
本发明的目的是提供新的具有高发光效率和热稳定性提高的发射红光的材料,用于制造发射稳定红光的有机EL器件,该器件具有高红色色度和高亮度。
本发明的另一目的是提供了包括上述材料的有机电致发光器件,通过使空穴和电子在发射层结合而有助于达到高亮度和高发光效率。
为了达到本发明的目的,本发明提供了用于制造发射红光的有机EL器件的,用下述式(1)表示的发射红光的化合物:
R1-CH=CH-X-CH=CH-R2
其中
R1,R2和R3各自独立地是式(2)、式(3)和式(4)或(5),
其中
R4,R5,R6,R7,R8和R9各自独立地是氢、卤素基团、取代或未取代的烷氧基、取代或未取代的烷基或取代或未取代的芳基(allyl)。
本发明优选的实施方案
上式的各个定义将在下文详细说明。
根据本发明,可用“烷基”的优选实例是具有1-5个碳原子的直链或支链的饱和烃基,例如甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、异戊基等,但更优选乙基基团。
可用“烷氧基”的优选实例是含有具有1-5个碳原子的直链或支链烷基的基团,例如甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、叔丁氧基、戊氧基、异戊氧基等,但更优选乙氧基基团。
可用“芳基”的优选实例是具有6-12个碳原子的芳族基团,例如苯基、萘基等,更优选萘基基团。
根据本发明,“取代基”的优选实例是氢原子、卤素基团、氰基、氨基、硝基、羧基、甲基、乙基、丙基、丁基、仲丁基、叔丁基、戊基、己基等,但对此没有限制。
有代表性的式(1)的实例如下:
化合物1 化合物2
化合物3 化合物4
化合物5 化合物6
化合物7 化合物8
化合物9 化合物10
化合物11 化合物12
化合物13 化合物14
化合物15 化合物16
化合物17 化合物18
化合物19 化合物20
化合物21 化合物22
但是,本发明不受这些有代表性的实例的限制。
另外,本发明提供了含有式(1)化合物的有机EL器件,更具体地,该有机EL器件在第一和第二电极之间形成具有一或多层有机薄层,其中在有机薄层中至少任意一层含有一种或多种本发明发射红光的材料。
式(1)化合物可以单独使用,可以结合的形式或作为掺杂其它材料的主体使用于任何所述的有机薄层,或用作其它空穴传输材料、发射材料或电子传输材料的掺杂剂。优选的,本发明的化合物可用作发射层的掺杂剂或主体材料。
使用本发明发射红光材料的有机EL器件可有多种实施方案。如果必要,基本上是将发射层引入一对电极(阳极和阴极)。然后,必要时,可引入空穴注射层和/或空穴注射层和/或电子注射层和/或电子传输层。更具体地,器件的结构实例是:(1)阳极/发射层/阴极;(2)阳极/空穴传输层/发射层/阴极;(3)阳极/空穴传输层/电子传输层/阴极;(4)阳极/空穴注射层/空穴传输层/发射层/阴极;(5)阳极/空穴注射层/空穴传输层/发射层/电子传输层/阴极;(6)阳极/空穴注射层/空穴传输层/发射层/电子传输层/电子注射层/阴极;(7)阳极/空穴注射层/发射层/电子注射层/阴极等。如果需要,上述结构的器件用基质支撑。对基质的存在没有特别的限制,可以使用用于有机EL器件的常规基质,例如玻璃、透明塑料、石英等。
构成本发明有机EL器件的每一层可按照常规的方法如沉积法、旋转涂布法或浇铸法应用所包含的材料形成层压的多层制品。
对用这些方法形成的各层,例如发射层的厚度没有特别的限制,根据器件的条件可以进行适当的选择。
此外,对于有机EL器件的阳极,可以使用功函数大于4.0eV的金属、合金、导电化合物,或它们的结合作为电极。这些电极材料的实例是导电的透明或不透明材料,如ITO、SnO2、ZnO、Au等。阳极可通过沉积、溅镀等方法形成薄膜而制造。
另外,对于有机EL器件的阴极,可以使用功函数大于4.2eV的金属、合金、导电化合物,或它们的结合作为电极。这些电极材料的实例是钙、镁、锂、铝、镁合金、锂合金、铝合金、铝/锂混合物、镁/银混合物、铟等。所述的阴极也可通过沉积、溅镀等方法形成薄膜而制造。
优选的,电极的薄膜电阻小于几百Ω/mm,膜的厚度选择在10nm-1μm范围内,优选50-200nm。
对本发明的有机EL器件,优选将阳极和阴极中的一个或二个制成透明或半透明的,通过阳极或阴极可以传输发光以提高发光的传输效率。
本发明的有机EL器件中,可以用作空穴注射层和空穴传输层的其它材料是光传导材料中通常用作空穴传输的任何材料,在已知材料中任何随机的(random)材料均可用作空穴注射层或空穴传输层。
对于本发明的有机EL器件,电子传输层包括电子传输化合物,并具有将注射到阴极的电子传输到发射层的作用。对这些电子传输化合物没有特别的限制,可以选择使用任何已知的常规化合物。
下面说明了制造本发明具有6(6)结构的有机EL器件的适用方法的一个实施方案:
首先,在透明基质上使用例如溅镀的方法形成第一电极。然后,通过真空沉积的方法在其上依次形成空穴注射层和空穴传输层。在此之后,在空穴传输层上依次形成有机发射层和电子传输层,在电子传输层上依次形成电子注射层和阴极。
发射层可用掺杂本发明的一种或多种式(1)掺杂剂的常用主体形成,或仅用一种或多种本发明的式(1)化合物形成。此外,本发明的式(1)化合物通过相互用作主体和掺杂剂形成发射层。
通常ITO(In2O3+SnO2)或IZO(In2O3+ZnO)可用于阳极材料,铜(II)酞青可用作空穴注射层材料。三苯胺或二苯胺类似物如NPD(N,N-二(萘基-1-基)-N,N′-二苯基联苯胺)可用作空穴传输层的材料,以及Alq3(三(8-喹啉醇化)铝)可用作发射层的主体材料。另外,由于Alq3具有良好的电子传输性能,因此也可用作电子传输层,噁二唑或三唑类似物如2-(4-二苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑也可用作电子传输层。碱金属(Cs,Rb,K,Na,Li)类似物(Li2O等)可用作电子注射层,以及Mg/Ag,Al,Al/Li或Al/Nd可用作阴极。
附图简要说明
结合下述附图的详细描述可以更清楚地理解本发明。
图1显示了常用有机EL器件的剖面视图。
发明详述
本发明式(1)化合物的合成实施例,以及应用所述化合物的有机EL器件通过下述合成实施例和应用实施例进行说明。在描述中将说明本发明其它的优点、目的和特性,这些在实践本发明时会更加清楚。在下述包括权利要求书的说明书中将会解释本发明的各种目的和优点。
[合成实施例]
[合成实施例1]
合成2,5-双-[2-(9-乙基-咔唑-3-基)-乙烯基]-对苯二腈(化合物1)
1)合成2,5-二甲基-对苯二腈
将60g 2,5-二溴-对二甲苯(0.227mol)、42.4g CuCN(0.568mol)和300ml二甲基甲酰胺加入圆底烧瓶,反应于130℃进行12小时。反应完成后,将反应混合物加入300ml水和300ml氨水溶液的混合溶液中,过滤其中形成的结晶。然后,将结晶再次加入100ml水和300ml氨水的混合溶液,混合,过滤,将得到的结晶加入2000ml甲苯中,加热溶解,用活性炭进行处理。真空蒸发滤液,向其中加入300ml己烷。得到20g白色结晶(0.128mol,产率:56%)。
2)合成2,5-二溴甲基-对苯二腈
将2g 2,5-二甲基-对苯二腈(0.0128mol)、1.9ml溴(0.384mol)和100ml二氯甲烷加入中压管,反应在60℃进行24小时。反应完成后,向其中加入200ml水,用2%氢氧化钠调节反应混合物的pH至10。分离有机层,用200ml水萃取二次,真空蒸发。将浓缩的结晶载于柱上,用己烷洗涤,得到1.1g产品(3.5mol,产率:27.5%)。
3)合成[2,5-二氰基-4-(二乙氧基-磷酰基甲基)-苄基]-膦酸二乙酯
将3g 2,5-二溴甲基-对苯二腈(9.55mmol)、6.6ml三乙氧基磷酸酯(0.038mol)和100ml甲苯加入圆底烧瓶,回流24小时。反应完成后,用活性炭处理反应混合物,真空蒸发滤液得到3g白色结晶(7.0mmol,产率:75%)。
4)合成2,5-双-[2-(9-乙基咔唑-3-基)-乙烯基]-对苯二腈
将1.3g[2,5-二氰基-4-(二乙氧基-磷酰基甲基)-苄基]-膦酸二乙酯(3.03mmol),1.4g 9-乙基咔唑甲醛和100ml四氢呋喃加入圆底烧瓶,将0.7g叔丁醇钾(6.37mmol)分几次缓慢加入反应混合物,得到的混合物在室温下搅拌1小时,向其中加入200ml水,过滤出得到的结晶,用50ml甲醇洗涤。将得到的结晶加入100ml二氯甲烷,混合,过滤,得到0.8g橙色结晶(1.41mmol,产率:46%)。最终化合物的熔点经测定为333℃。
[合成实施例2]
合成2,5-双-[2-(10-乙基-phenocyazin-3-基)-乙烯基]-对苯二腈(化合物4)
将1.3g[2,5-二氰基-4-(二乙氧基-磷酰基甲基)-苄基]-膦酸二乙酯(3.03mmol)、1.54g 10-乙基-3-phenocyazine甲醛(6.06mmol)和100ml四氢呋喃加入圆底烧瓶,将0.7g叔丁醇钾(6.37mmol)分几次缓慢加入反应混合物,得到的混合物在室温下搅拌1小时。然后向其中加入200ml水,过滤出得到的结晶,用50ml甲醇洗涤。在得到的结晶中加入100ml二氯甲烷,搅拌,过滤,得到0.94g橙色结晶(产率:49%)。
[合成实施例3]
合成2,5-双-[2-(10-乙基-吩噁嗪-3-基)-乙烯基]-对苯二腈(化合物7)
将1.3g[2,5-二氰基-4-(二乙氧基-磷酰基甲基)-苄基]-膦酸二乙酯(3.03mmol)、1.45g 10-乙基-3-吩噁嗪(phenocyazine)甲醛(6.06mmol)和100ml四氢呋喃加入圆底烧瓶,将0.7g叔丁醇钾(6.37mmol)分几次缓慢加入反应混合物,得到的混合物在室温下搅拌1小时。然后向其中加入200ml水,过滤出得到的结晶,用50ml甲醇洗涤。在得到的结晶中加入100ml二氯甲烷,搅拌,过滤,得到0.72g橙色结晶(产率:39%)。
[合成实施例4]
合成2,5-双-[4-(三苯氨基)-乙烯基]-对苯二腈(化合物10)
将1.3g[2,5-二氰基-4-(二乙氧基-磷酰基甲基)-苄基]-膦酸二乙酯(3.03mmol)、1.65g 4-甲酰基三苯基甲醛(6.06mmol)和100ml四氢呋喃加入圆底烧瓶。将0.7g叔丁醇钾(6.37mmol)分几次缓慢加入反应混合物,然后回流和冷却反应混合物得到结晶。过滤出得到的结晶,用200ml甲醇洗涤。在得到的结晶中加入100ml二氯甲烷,搅拌,过滤,得到0.8g橙色结晶(1.41mmol,产率:39%)。
[合成实施例5]
合成化合物22
1)合成2,4,6-三溴-1,3,5-三甲苯
将含溴的粗液(14ml,0.27mmol)、铁粉(4g,72mmol)和四氯化碳(30ml)加入反应容器,然后用1小时向其中缓慢加入1,3,5-三甲苯(2ml,14mmol)。再搅拌反应混合物1小时,然后加入过量的Na2S2O3溶液,以除去溴。该溶液用水/氯仿萃取,以除去其中的溶剂,用混合溶剂(甲苯/丙酮=1/5)重结晶后得到白色产品[产率:3.5g(70%以上)]
2)合成2,4,6-三氰基-1,3,5-三甲苯(TCM)
将CuCN(220g,243mmol)和吡啶(146.7g,1.85mol)加入高压反应器,充分混合,然后向其中加入2,4,6-三溴-1,3,5-三甲苯(25g,75.8mmol)。反应混合物于205℃反应2小时。其中的铜用过量的甲二胺除去,然后用MC过滤。反应混合物中的水用MgSO4除去,然后真空蒸发其中的溶剂。残余物用硅胶柱吸附,用柱(tube)色谱分离(Hx∶MC=3∶1),得到白色固体[产率:6g(40.59%)]。
3)合成2,4,6-三氰基-溴甲基苯-1,3,5-三腈(TCBM)
将TCM(1g,5.128mmol)、溴(2.86g,17.248mmol)和四氯化碳(10ml)加入光反应器,然后用钨灯反应8小时。反应混合物用MC萃取,用MgSO4除去水,真空蒸发除去溶剂,残余物用柱色谱分离(Hx∶EA=8∶1)得到白色固体[产率:1.32g(60%)]。
4)合成(2,4,6三氰基-3,5-双[二乙氧基-磷酰基]-苯基)-膦酸二乙酯(TCPM)
在反应器中加入TCBM(1g,2.32mmol)、三乙基亚磷酸酯(1.616g,13.92mmol)和甲苯(过量),回流8小时。真空蒸发除去溶剂后残余物用柱色谱分离(Hx∶MC=3∶1)得到黄色固体[产率:0.84g(60%)]。
5)合成间甲苯基-二-对甲苯基胺(m-toryl-di-p-torylamine)(MTPA)
在干燥炉干燥的高压管中充满氩气,然后向其中加入间甲苯胺(m-toryl amine)(1g,9mmol),1-溴-4-甲基苯(6.2g,36mmol)、pd(dba)3(0.39g,0.43mmol)、DPPF(0.48,0.86mmol)、NaOtBu(4.1g,43mmol)和甲苯(20ml),于120℃搅拌72小时。反应混合物用MC萃取,真空蒸发溶剂。残余物用柱色谱过滤(Hx∶EA=10∶1),用己烷重结晶得到白色固体[产率:1.07g(40%)]。
6)合成TPAD
将MTPA(0.2g,0.69mmol)溶解于DMF(20ml)后,在0℃下向其中滴加POCl3(0.15g,1mmol)。搅拌反应混合物30分钟以上,然后将温度提高到90℃再反应4小时。将反应混合物加入到50ml冰水中,用20%NaOH溶液中和,用MC萃取。真空蒸发除去溶剂后,残余物用柱色谱分离(Hx∶EA=15∶1)[产率:0.16g(80%)]。
7)合成化合物22
在72℃的条件下,将LDA(0.84ml,0.51mmol)加入TCPM(0.1g,0.17mmol)的10ml THF溶液,30分钟后撤去温浴,继续搅拌反应混合物30分钟。然后使其温度下降,滴加TPAD(0.16g,0.51mmol),搅拌,30分钟后撤去温浴30分钟,使其过夜。残余物用柱色谱分离(Hx∶EA=1∶4)[M.P.:280℃,产率:0.070g(38%)]。
包括式(1)的其它化合物通过与合成实施例1-5类似的方法合成。将上述如此合成的材料用真空升华设备进一步纯化,以便用于有机EL器件。
[实施例1]
在此实施例中,制造了以化合物10为掺杂剂和以Alq3为发射红光的发射层主体的有机EL器件。
首先,在用微波洗涤的沉积了ITO的玻璃上真空沉积厚度30nm的CuPC(酞菁铜(II))形成空穴注射层。然后,在其上真空沉积厚度为50nm的NPD(N,N′-二萘基-N,N′-二苯基-(1,1′-联苯基)-4,4′-二胺)而形成空穴传输层之后,在该空穴传输层上沉积厚度为30nm的Alq3(主体)而形成发射层,Alq3中掺杂了1.0%的化合物10(掺杂剂)。通过真空沉积在其上依次形成电子传输层(Alq3;40nm)、电子注射层(Li2O;25nm)和阴极(Mg/Ag;100nm),从而获得有机EL器件。
将正向偏压的直流电压(direct voltage of forward bias)加于实施例1制备的有机EL器件上,对其发光性能进行评价。发光的颜色是红色。光谱学测试的结果是谱图的发光峰在605nm左右。另外,在电压-亮度实验中,在8V时的亮度为5,400cd/m2,在这一点上的效率是1.88lm/W(见表1)。
[实施例2]
在本实施例中,制造了用化合物1作为主体和以DCM作为红色发射层的掺杂剂的有机EL器件。
首先,在用微波洗涤的沉积了ITO的玻璃上真空沉积厚度30nm的CuPC形成空穴注射层。然后,在其上真空沉积厚度为50nm的NPD(N,N′-二萘基-N,N′-苯基-(1,1′-联苯基)-4,4′-二胺)形成空穴传输层,之后在空穴传输层上沉积厚度为30nm的化合物1(主体)而形成发射层,化合物1中掺杂了1.0%的DCM(掺杂剂)。通过真空沉积在其上依次形成电子传输层(Alq3;40nm)、电子注射层(Li2O;25nm)和阴极(Mg/Ag;100nm),从而获得有机EL器件。
将正向偏压的直流电压加于实施例2制备的有机EL器件上,对其发光性能进行评价。发光的颜色是红色。光谱学测试的结果是谱图的发光峰在609nm左右。另外,在电压-亮度实验中,在8V时的亮度为5,740cd/m2,在这一点上的效率是1.92lm/W(见表1)。
[实施例3]
在本实施例中,制造了用化合物22作为主体和以DCM作为红色发射层的掺杂剂的有机EL器件。
首先,在用微波洗涤的沉积了ITO的玻璃上真空沉积厚度30nm的CuPC形成空穴注射层。然后,在其上真空沉积厚度为50nm的NPD(N,N′-二萘基-N,N′-苯基-(1,1′-联苯基)-4,4′-二胺)形成空穴传输层,之后在该空穴传输层上沉积厚度为30nm的化合物22(主体)而形成发射层,化合物22中掺杂了1.0%的DCM(掺杂剂)。通过真空沉积在其上依次形成电子传输层(Alq3;40nm)、电子注射层(Li2O;25nm)和阴极(Mg/Ag;100nm),从而获得有机EL器件。
将正向偏压的直流电压加于实施例3制备的有机EL器件上,对其发光性能进行评价。发光的颜色是红色。光谱学测试的结果是谱图的发光峰在621nm左右。另外,在电压-亮度实验中,在8V时的亮度为3,872cd/m2,在这一点上的效率是1.48lm/W(见表1)。
[实施例4]
在本实施例中,制造了用化合物1作为主体和以化合物22作为红色发射层的掺杂剂的有机EL器件。
首先,在用微波洗涤的沉积了ITO的玻璃上真空沉积厚度30nm的CuPC形成空穴注射层。然后,在其上真空沉积厚度为50nm的NPD(N,N′-二萘基-N,N′-苯基-(1,1′-联苯基)-4,4′-二胺)形成空穴传输层,之后在该空穴传输层上沉积厚度为30nm的化合物1(主体)而形成发射层,化合物1中掺杂了1.0%的化合物22(掺杂剂)。通过真空沉积在其上依次形成电子传输层(Alq3;40nm)、电子注射层(Li2O;25nm)和阴极(Mg/Ag;100nm),从而获得有机EL器件。
将正向偏压的直流电压加于实施例4制备的有机EL器件上,对其发光性能进行评价。发光的颜色是红色。光谱学测试的结果是谱图的发光峰在617nm左右。另外,在电压-亮度实验中,在8V时的亮度为4,200cd/m2,在这一点上的效率是1.55lm/W(见表1)。
各实施例的结果综合列于表1。
表1
主体 | 掺杂剂 | 应用电压(V) | 亮度(cd/m2) | 效率(lm/W) | 光谱(nm) | |
实施例1 | Alq3 | 化合物10 | 8.0 | 5,400 | 1.88 | 605nm |
实施例2 | 化合物1 | DCM | 8.7 | 5,740 | 1.92 | 609nm |
实施例3 | 化合物22 | DCM | 8.5 | 3,872 | 1.48 | 621nm |
实施例4 | 化合物1 | 化合物22 | 7.8 | 4,200 | 1.55 | 617nm |
如上表所述,与使用常规发射红光的材料相比,应用了本发明发射红光材料的有机EL器件显示了特别优异的发光效率和亮度。另外,本发明的材料还增强了器件的安全性和使用寿命。
Claims (7)
1.由下式(1)表示的化合物:
R1-CH=CH-X-CH=CH-R2
其中:
X是
或
R1,R2和R3各自独立地是式(2)、式(3)、或式(4)或式(5):
其中
R4、R5、R6、R7、R8和R9各自独立地是氢、卤素基团、取代或未取代的烷氧基、取代或未取代的烷基或取代或未取代的芳基。
3.有机电致发光器件,该器件在第一电极和第二电极之间形成具有一或多层的有机薄层,其中至少任意一层有机薄层含有一种或多种权利要求1或2中式(1)表示的化合物。
4.按照权利要求3的有机电致发光器件,其中所述的有机薄层含有一或多层选自下述的各层:空穴传输层、发射层、空穴保护层(ahole blocking layer)、电子传输层和空穴注射层。
5.按照权利要求4的有机电致发光器件,其中至少一种或多种权利要求1或2的式(1)表示的化合物被用作发射层的掺杂剂。
6.按照权利要求4的有机电致发光器件,其中至少一种或多种权利要求1或2的式(1)表示的化合物被用作发射层的主体。
7.按照权利要求4的有机电致发光器件,其中至少一种或多种权利要求1或2的式(1)表示的化合物可被用作发射层的主体和掺杂剂两者。
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CN101747383A (zh) * | 2008-11-28 | 2010-06-23 | 三星电子株式会社 | 含磷光单元的化合物、含其的发光聚合物及有机发光器件 |
CN101294004B (zh) * | 2008-04-21 | 2011-12-21 | 大连七色光太阳能科技开发有限公司 | 一类吩恶嗪染料及其在染料敏化太阳能电池中的应用 |
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JP4541108B2 (ja) * | 2004-04-26 | 2010-09-08 | パナソニック株式会社 | プラズマディスプレイ装置 |
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US10715209B2 (en) | 2006-11-18 | 2020-07-14 | RF Micron, Inc. | Computing device for processing environmental sensed conditions |
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JP3852518B2 (ja) * | 1998-05-18 | 2006-11-29 | ソニー株式会社 | 有機電界発光素子 |
JP3852517B2 (ja) * | 1998-05-18 | 2006-11-29 | ソニー株式会社 | 有機電界発光素子 |
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JP2000012225A (ja) * | 1998-06-26 | 2000-01-14 | Sony Corp | 有機電界発光素子 |
US6525212B1 (en) * | 1998-12-07 | 2003-02-25 | Sony Corporation | Bis(aminostyryl)benzene compounds and synthetic intermediates thereof, and process for preparing the compounds and intermediates |
JP4411708B2 (ja) * | 1998-12-07 | 2010-02-10 | ソニー株式会社 | ビス(アミノスチリル)ベンゼン化合物 |
JP2001043974A (ja) * | 1999-07-30 | 2001-02-16 | Sony Corp | 有機電界発光素子にこれらの製造方法 |
JP2001291591A (ja) * | 2000-04-07 | 2001-10-19 | Sony Corp | 有機電界発光素子及び発光装置 |
JP2001307884A (ja) * | 2000-04-26 | 2001-11-02 | Toray Ind Inc | 発光素子 |
KR100454586B1 (ko) * | 2001-07-27 | 2004-11-03 | 학교법인고려중앙학원 | 1,3,5-트리시아노-2,4,6-트리스(비닐)벤젠 유도체 및 그제조방법 |
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CN101294004B (zh) * | 2008-04-21 | 2011-12-21 | 大连七色光太阳能科技开发有限公司 | 一类吩恶嗪染料及其在染料敏化太阳能电池中的应用 |
CN101747383A (zh) * | 2008-11-28 | 2010-06-23 | 三星电子株式会社 | 含磷光单元的化合物、含其的发光聚合物及有机发光器件 |
US9206170B2 (en) | 2008-11-28 | 2015-12-08 | Samsung Electronics Co., Ltd. | Compound comprising phosphorescence unit, emitting polymer and organic emitting device comprising the emitting polymer |
CN109810046A (zh) * | 2019-01-20 | 2019-05-28 | 浙江工业大学 | D-π-A-π-D′化合物及其合成和应用 |
CN109810046B (zh) * | 2019-01-20 | 2020-10-02 | 浙江工业大学 | D-π-A-π-D′化合物及其合成和应用 |
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US7261952B2 (en) | 2007-08-28 |
DE60321399D1 (de) | 2008-07-10 |
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ATE397054T1 (de) | 2008-06-15 |
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US20040137273A1 (en) | 2004-07-15 |
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