CN113248476B - 一种有机化合物及使用该化合物的有机发光器件 - Google Patents
一种有机化合物及使用该化合物的有机发光器件 Download PDFInfo
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- CN113248476B CN113248476B CN202110372697.5A CN202110372697A CN113248476B CN 113248476 B CN113248476 B CN 113248476B CN 202110372697 A CN202110372697 A CN 202110372697A CN 113248476 B CN113248476 B CN 113248476B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 10
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 229940078552 o-xylene Drugs 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- MTBRQOGPXZHFAH-UHFFFAOYSA-N 3-anilino-2-pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one Chemical compound C1(=CC=CC=C1)NC1=C(NC2=C1C(NCC2)=O)C1=CC=NC=C1 MTBRQOGPXZHFAH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 2
- OWWVTWHBNAWUJO-UHFFFAOYSA-N 4-iodo-n,n-diphenylaniline Chemical compound C1=CC(I)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 OWWVTWHBNAWUJO-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- UJORPFQWUKFXIE-UHFFFAOYSA-N 2-[1-[(4-ethoxy-2,6-difluorophenyl)methyl]-5,6-dihydro-4h-cyclopenta[c]pyrazol-3-yl]-5-methoxy-n-pyridin-4-ylpyrimidin-4-amine Chemical compound FC1=CC(OCC)=CC(F)=C1CN1C(CCC2)=C2C(C=2N=C(NC=3C=CN=CC=3)C(OC)=CN=2)=N1 UJORPFQWUKFXIE-UHFFFAOYSA-N 0.000 description 1
- PJRGCJBBXGNEGD-UHFFFAOYSA-N 2-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(Br)C=C3NC2=C1 PJRGCJBBXGNEGD-UHFFFAOYSA-N 0.000 description 1
- WQNMOPRHXVYQIS-UHFFFAOYSA-N B(O)O.C1=CC=CC=2C3=CC=CC=C3NC12 Chemical compound B(O)O.C1=CC=CC=2C3=CC=CC=C3NC12 WQNMOPRHXVYQIS-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L PdCl2(PPh3)2 Substances [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical group O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- -1 carbazole series compounds Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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Abstract
Description
技术领域
本发明涉及一种有机化合物和使用该化合物的有机发光器件,更具体而言,涉及一种具 有优异的色纯度和高亮度及发光效率的可溶性有机化合物以及使用该化合物的OLED器件。
背景技术
随着多媒体技术的发展及信息化要求的提高,对面板显示器性能的要求越来越高。其中, OLED具有自主发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列的优点,在新 一代显示器和照明技术中的潜在应用而引起广泛注意,应用前景十分广阔。有机电致发光器 件是自发的发光器件,OLED发光的机理是在外加电场作用下,电子和空穴分别从正负两极 注入后在有机材料中迁移、复合并衰减而产生发光。OLED的典型结构包括阴极层、阳极层、 电子注入层、电子传输层、空穴阻挡层、空穴传输层、空穴注入层和有机发光层中的一种或 几种功能层。
尽管有机电致发光的研究进展非常迅速,但仍有很多亟待解决的问题,比如外量子效率 (EQE)的提高,色纯度更高的新材料的设计与合成、高效电子传输/空穴阻挡新材料的设计与 合成等。对于有机电致发光器件来说,器件的发光量子效率是各种因素的综合反映,也是衡 量器件品质的一个重要指标。
发光可以分为荧光发光和磷光发光。在荧光发光中,单线态激发状态的有机分子跃迁至 基态,由此发出光。另一方面,在磷光发光中,三线态激发状态的有机分子跃迁至基态,由 此发出光。
目前来看,部分有机电致发光材料由于其性能优秀,已经在商业上有所应用,但作为有 机电致发光器件中的主体材料,除了三线态能级要高于客体材料,防止激子跃迁释放的能量 逆传递以外,更重要的是具有良好的空穴迁移性能。目前,主体材料中同时具有高三线态能 级和良好空穴迁移率的材料仍然缺乏。因此,如何设计新的性能更好的主体材料,一直是本 领域技术人员亟待解决的问题。
发明内容
本发明的目的是提供一种有机化合物及其使用该化合物的有机发光器件,本发明的有机 化合物具有优异的纯色度、高亮度和优异的发光效率
本发明提供一种有机化合物,其结构式如1所示,
上述的结构式中,Ar1和Ar2中一个是必须取代或未取代的C4-C90杂芳基、包含氮(N) 的杂环基或胺系列基团,另外一个是取代或未取代的包含氮原子两个以上的C6-C90杂芳基或杂环 基。
优选的,一种有机化合物,其特征在于:其结构式如1-1~1-2所示:
其中,Ar1和Ar2中一个是必须取代或未取代的C4-C90杂芳基、包含氮(N)的杂 环基或胺系列基团,另外一个是取代或未取代的包含氮原子两个以上的C6-C90杂芳基 或杂环基。
R1和R2各自独立地选自取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠环基、取代或未取代的C4-C30杂芳基、取代或未取代的C13-C30胺衍生物或芴衍生物, R1和R2可以链接形成环;
L是单键或选自取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠环基、 取代或未取代的C4-C30杂芳基。
进一步的优选的方式是,有机化合物结构中Ar1和Ar2独立地选自以下结构:
其中,R3和R4独立的选自取代或未取代的C1-C15烷基、取代或未取代的C6~C30芳基、 取代或未取代的C4~C30杂芳基、或者是它们的组合中的一种;
X1、X2、X3独立的选自氮(N)或碳(C);
L1是单键或选自取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠环基、取代 或未取代的C4-C30杂芳基。
进一步的优选的方式是,有机化合物结构中R1和R2独立地选自以下结构:
其中,R8、R9和R10独立的选自取代或未取代的C1-C15烷基、取代或未取代的C6~C30 芳基、取代或未取代的C4~C30杂芳基、或者是它们的组合中的一种;
L2是单键或选自取代或未取代的C6-C30芳基、取代或未取代的C10-C30稠环基、取代 或未取代的C4-C30杂芳基。
进一步的优选的方式是,所述的有机化合物独立地选自下列化合物:
本发明还提供上述一种含咔唑系列的化合物在有机发光器件中的应用。
优选的,所述有机发光器件包括阳极、阴极以及位于阳极与阴极之间的若干个有机功能 层,所述的有机功能层含有所述的一种含咔唑系列的化合物。
本发明的有益效果:
本发明提供一种含咔唑系列的化合物,该含咔唑系列的化合物具有式1所示结构,咔唑 系列的化合物中富电子的结构对整个化合物分子的光电性质产生很大的影响,有利于减少不 必要的振动能量损失,实现高效的发光性能。通过调节取代基基团,使化合物具有更好的热 稳定性和化学性质。本发明的一种含咔唑系列的化合物,制备方法简单,原料易得,能够满 足工业化需求。
将咔唑系列的化合物制备成器件,尤其是作为主体材料,器件表现出驱动电压低、发光 效率高的优点,优于现有常用OLED器件。
在本发明中,所述有机电致器件优选包括阳极、阴极以及位于阳极和阴极之间的若干个 有机物层,所述“有机物层”指的是有机电致器件中阳极和阴极之间部署的全部层的术语。所 述有机物层可以是具有空穴特性的层和具有电子特性的层。比如,所述有机物层包括空穴注 入层、空穴传输层、既具备空穴注入又具备空穴传输的技能层、电子阻挡层、发光层、空穴 阻挡层、电子传输层、电子注入层、既具备电子传输又具备电子注入的技能层中的一种或几 种。
在本发明中,所述空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输的技能层 中可以采用常规的空穴注入物质、空穴传输物质、既具备空穴注入又具备空穴传输技能的物 质以外再包括电子-生成的物质。
比如,所述有机物层是包括发光层,所述发光层是包括磷光主体、荧光主体、磷光掺杂 和荧光掺杂中的一种或几种。在本发明中,可以采用所述有机电致器件用化合物作为荧光主 体,也可以作为荧光掺杂,以及同时作为荧光主体和荧光掺杂。
在本发明中,所述发光层可以为红色、黄色或蓝色发光层。在本发明中,所述发光层为 发光层时,采用上述所述的有机电致器件用化合物作为主体,可得到高效率、高分辨率、高 亮度及长寿命的有机电致器件。
在本发明中,所述的有机化合物的有机电致发光二极管器件,其特征在于,所述的有机 电致发光器件包括顺次沉积的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子 注入层和阴极,所述有机化合物作为发光层的主体材料。
本发明对所述有机电致器件的制备方法没有特殊的限制,除了使用式1的有机化合物之 外,采用本领域技术人员熟知的发光器件的制备方法和材料制备得到即可。
具体实施方式
为了使本发明实现的技术手段、创作特征、达成目的与功效易于明白了解,下面结合具 体实施例,进一步阐述本发明。
实施例1:化合物1-1的合成
1、中间体1-1-1的合成
在250毫升三口烧瓶中加入中间体2-溴-4H-苯并[def]咔唑(5.40克,20毫摩),4-碘-N, N-二苯基苯胺(7.80克,21.0毫摩),三(二亚苄基丙酮)二钯(4摩%),三叔丁基膦(8摩%),叔 丁醇钾(3.8克,33.6毫摩)和邻二甲苯(80毫升)。反应体系升温至120摄氏度,氮气保护下反应 12小时。反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干 燥、浓缩、重结晶所得粗品过硅胶柱得到化合物1-1-1(8.73克,收率85%)。
LC-M/Z512.09(M+H)+。
2、中间体1-1-2的合成
在500毫升反应瓶中加入中间体咔唑硼酸(12.96克,61.4毫摩),1-1-1(31.52克,61.4毫摩), 四(三苯基膦)钯(5摩%),K2CO3(17.0克,122.8毫摩),1,4-二氧六环(200毫升)和水(50毫升)。 反应体系升温至80摄氏度,氮气保护下反应12小时。反应完成后,将反应液冷却至室温, 用邻二氯苯和水萃取。有机层用无水硫酸镁干燥、浓缩、重结晶所得粗品过硅胶柱得到中间 体1-1-2(25.78克,收率70%)。LC-MS:M/Z599.24(M+H)+。
3、化合物1-1的合成
在250毫升三口烧瓶中加入中间体1-1-2(11.99克,20毫摩),2-氯-4-苯基喹唑啉(5.05克, 21.0毫摩),三(二亚苄基丙酮)二钯(4摩%),三叔丁基膦(8摩%),叔丁醇钾(3.8克,33.6毫摩) 和邻二甲苯(80毫升)。反应体系升温至120摄氏度,氮气保护下反应12小时。反应完成后, 将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥、浓缩、重结晶所得 粗品过硅胶柱得到化合物1-1(11.58克,收率72%)。LC-MS:M/Z803.31(M+H)+。
实施例2:化合物2-1的合成
1、中间体2-1-1的合成
在250毫升三口烧瓶中加入中间体2-溴-9H咔唑(4.92克,20毫摩),4-碘-N,N-二苯基 苯胺(7.80克,21.0毫摩),三(二亚苄基丙酮)二钯(4摩%),三叔丁基膦(8摩%),叔丁醇钾(3.8 克,33.6毫摩)和邻二甲苯(80毫升)。反应体系升温至120摄氏度,氮气保护下反应12小时。 反应完成后,将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥、浓缩、 重结晶所得粗品过硅胶柱得到化合物2-1-1(8.81克,收率90%)。LC-MS:M/488.09(M+H)+。
2、中间体2-1-2的合成
在氮气保护条件下,向三口瓶中加入2-1-1(23.53克,81.3毫摩),联硼酸频那醇酯(24.8克, 97.5毫摩),三苯基膦(6摩%),反-二(三苯基膦)二氯化钯(II)(3摩%),苯酚钾(16.1克,121.9毫 摩)和无水甲苯(500毫升)。氮气置换后在50摄氏度条件下搅拌反应5小时,然后将体系冷却 到室温并加水猝灭反应。反应混合物用苯溶剂和饱和食盐水萃取。取有机相用无水硫酸镁 2-1-2(34.89克,收率80%)。LC-MS:M/Z 536.26(M+H)+
3、中间体2-1-3的合成
在500毫升反应瓶中加入中间体2-1-2(32.94克,61.4毫摩),2-溴-4H-苯并[def]咔唑(16.59 克,61.4毫摩),四(三苯基膦)钯(5摩%),碳酸钾(17.0克,122.8毫摩),1,4-二氧六环(200毫升) 和水(50毫升)。反应体系升温至80摄氏度,氮气保护下反应12小时。反应完成后,将反应 液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥、浓缩、重结晶所得粗品过 硅胶柱得到中间体2-1-3(25.04克,收率68%)。LC-MS:M/Z599.24(M+H)+。
4、化合物2-1的合成
在250毫升三口烧瓶中加入中间体2-1-3(11.99克,20毫摩),2-氯-4-苯基喹唑啉(5.05克, 21.0毫摩),三(二亚苄基丙酮)二钯(4摩%),三叔丁基膦(8摩%),叔丁醇钾(3.8克,33.6毫摩) 和邻二甲苯(80毫升)。反应体系升温至120摄氏度,氮气保护下反应12小时。反应完成后, 将反应液冷却至室温,用邻二氯苯和水萃取。有机层用无水硫酸镁干燥、浓缩、重结晶所得 粗品过硅胶柱得到化合物2-1(11.26克,收率70%)。LC-MS:M/Z803.29(M+H)+。
实施例3:化合物1-2的合成
参考实施例1的方法合成化合物1-2,,得到化合物1-2(8.15克,收率65%)。LC-MS:M/Z830.32(M+H)+。
实施例4:化合物1-4的合成
参考实施例1的方法合成化合1-4,,得到化合物1-4(8.55克,收率71%)。LC-MS:M/Z879.34(M+H)+。
实施例5:化合物2-3的合成
参考实施例2的方法合成化合物2-3,得到化合物2-3(6.34克,收率55%)。LC-MS:M/Z803.30(M+H)+。
实施例6:化合物2-47的合成
参考实施例2的方法合成化合物2-47,,得到化合物2-47(7.46克,收率66%)。LC-MS: M/Z801.29(M+H)+。
评价例1:化合物的HOMO、LUMO、三重态能级及S1-T1能级评价:
上面数据看出化合物中导入胺系列化合物以后物质的HOMO值降低、Eg(eV)值越符合RH(磷光红光主体材料)条件,另外导入胺系列化合物以后延迟荧光性能(S1-T1)加强。
器件实施方案
(I)发光材料器件的评价
器件实施例中所用的各有机层化合物如下所示:
1.第一实施方案
使ITO玻璃基板图案化,以具有毫米×3毫米的发光区域。然后洗涤图案化的ITO玻璃基 板。
随后将该基板安放在真空室。标准压力设定为1×10-6托。此后在ITO基板上以HIL HI-2/>HTL-1/>化合物1-1+RD-1((5%)/>ET-1/>LiF/>和Al/>的顺序形成有机物质的层。
2.第二实施方案
采用上述第一实施方案同样的方法制备第二实施方案的有机发光器件,仅把有机发光器 件的主体材料层由第一实施方案化合物1-1替换为化合物1-2。
3.第三实施方案
采用上述第一实施方案同样的方法制备第三实施方案的有机发光器件,仅把有机发光器 件的主体材料层由第一实施方案化合物1-1替换为化合物1-4。
4.第四实施方案
采用上述第一实施方案同样的方法制备第四实施方案的有机发光器件,仅把有机发光器 件的主体材料层由第一实施方案化合物1-1替换为化合物2-1。
5.第五实施方案
采用上述第一实施方案同样的方法制备第五实施方案的有机发光器件,仅把有机发光器 件的主体材料层由第一实施方案化合物1-1替换为化合物2-3。
6.第六实施方案
采用上述第一实施方案同样的方法制备第五实施方案的有机发光器件,仅把有机发光器 件的主体材料层由第一实施方案化合物1-1替换为化合物2-47。
7、对比例1
采用上述第一实施方案同样的方法制备对比例的有机发光器件,仅把有机发光器件的主 体材料层由第一实施方案化合物II-1替换为化合物RH 1。
8、对比例2
采用上述第一实施方案同样的方法制备对比例的有机发光器件,仅把有机发光器件的主 体材料层由第一实施方案化合物II-1替换为化合物RH 6。
制作的有机发光器件在10mA/cm2电流条件下测试电压、效率和寿命。
表1为本发明实施例和比较例制备得到的有机发光器件的性能检测结果。
表1
如表1所示,该器件在低电压下也高效率地运行。并且类似结构中与对比例相比,实施 方案的电流效率和寿命明显改善。
以上描述了本发明的基本原理、主要特征和本发明的优点。本行业的技术人员应该了解, 本发明不受上述实施例的限制,上述实施例和说明书中描述的只是说明本发明的原理,在不 脱离本发明精神和范围的前提下本发明还会有各种变化和改进,这些变化和改进都落入要求 保护的本发明范围内。
Claims (8)
5.一种使用权利要求1-3中任意一项所述的有机化合物的有机发光器件,其特征在于:所述的有机发光器件顺次包括沉积的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极,所述有机化合物作为发光层的主体材料。
6.根据权利要求5所述的有机发光器件,其特征在于,权利要求1-3中任意一项所述的化合物可以单独使用,或和其他化合物混合使用。
7.根据权利要求5所述的有机发光器件,其特征在于,使用权利要求1-3中任意一项所述的化合物做空穴阻挡层。
8.根据权利要求5所述的有机发光器件,其特征在于,使用权利要求1-3中任意一项所述的化合物做电子传输层。
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