CN111333647A - 有机电致发光材料及其应用 - Google Patents
有机电致发光材料及其应用 Download PDFInfo
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- CN111333647A CN111333647A CN201811566947.3A CN201811566947A CN111333647A CN 111333647 A CN111333647 A CN 111333647A CN 201811566947 A CN201811566947 A CN 201811566947A CN 111333647 A CN111333647 A CN 111333647A
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- 239000000463 material Substances 0.000 title claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000010410 layer Substances 0.000 claims description 48
- 238000002347 injection Methods 0.000 claims description 19
- 239000007924 injection Substances 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 238000007740 vapor deposition Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 abstract description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 benzofuran-2-boronic acid ester Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- 238000005166 mechanoluminescence Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
本发明提供了一种有机电致发光材料及其应用。本发明的有机电致发光材料含有吡嗪和氰基，具有化学式(I)结构。使用本发明中的化合物掺杂制备有机电致发光器件能够显著提高功率效率，并且可以降低启亮电压。
Description
技术领域
本发明涉及有机电致发光材料领域，具体涉及一种含有吡嗪和氰基的电致发光材料及其应用。
背景技术
近年来，有机发光二极管(OLED)作为一种有巨大应用前景的照明、显示技术，受到了学术界与产业界的广泛关注。OLED器件具有自发光、广视角、反应时间短及可制备柔性器件等特性，成为下一代显示、照明技术的有力竞争者。但目前OLED仍然存在效率低、寿命短等问题，有待人们进一步研究。
自1998年Forrest等人报道电致磷光器件(PHOLED)以来，有机电致发光器件已经实现了在产业上的应用。其优势在于突破了有机电致发光量子效率小于25％的限制，将量子产率提升至了100％。高效PHOLED器件通常为多层结构，包括阴极、阳极和有机层，所述有机层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的一层或多层，这些有机层不必每层都存在，可根据实际情况增加或减少部分有机层。其优点在于可以方便地调节载流子注入、传输及复合等过程，以提高载流子传输和复合效率。
有机电致发光器件性能优化的一个重要方面在于调节相邻有机功能层之间的电荷注入，来促进激子的形成，从而提高发光效率。TCNQF4常被用作空穴注入层，可有效地促进空穴的注入，降低驱动电压。但由于其分子量较小，具有很好的挥发性，导致在蒸镀过程中容易污染蒸镀仪和器件。
发明内容
本发明目的在于提供一种含有吡嗪和氰基的有机电致发光材料，该类材料可以有效地降低器件电压，同时提升效率。
有机电致发光材料，为具有式(I)结构的化合物：
其中：
B选自O、S、NR1，R1选自C1-C6的烷基、C3-C40的杂芳基、C6-C40的芳香基；
X1-X4独立地选自N、CR2，R2选自氢、氘、C1-C6的烷基、C3-C40的杂芳基、C6-C40的芳香基。
优选地，B选自O、S、NR1，R1选自C1-C6的烷基、C3-C9的杂芳基、C6-C14的芳香基；
X1-X4独立地选自N、CR2，R2选自氢、氘、C1-C6的烷基、C3-C9的杂芳基、C6-C14的芳香基。
优选地，B选自O、S、NR1，R1选自甲基、苯基、甲苯基、萘基、吡啶基；
X1-X4独立地选自N、CH。
更优选地，B选自O、S、NR1，R1选自甲基、苯基、吡啶基；
X1-X4独立地选自N、C H。
更优选地，B选自O、S、NR1，R1选自甲基、苯基、吡啶基；
X1-X4中有0-2个为N，其余为C H。
进一步优选，本发明的式(I)所述的发光材料为如下1-18化合物，但不限于所列举的结构：
上述化合物可以应用在有机电致发光器件，力致发光器件，有机场效应晶体管，有机太阳能电池和化学传感器中。
本发明对化学式(I)所述化合物的制备方法不做具体限定，典型但非限制性的以化合物
作为示例性实例，其合成与制备方法如下：
合成路线：
合成方法：
反应物1a(1eq)和苯并呋喃-2-硼酸酯1b(2.1eq)在氮气保护下经Pd催化的偶联反应得到中间体1c。1c经分子内关环反应得中间体1d，随后经缩合反应即得化合物1。
本领域的技术人员应该明了，上述制备方法只是一个示范性例子。本领域的技术人员可以通过对其技术改进获得本发明中的其他化合物。
本发明中的有机电致发光器件，包括阴极、阳极和有机层，所述有机层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的一层或多层，这些有机层不必每层都存在。
所述空穴注入层、空穴传输层、空穴阻挡层、发光层和/或电子传输层中至少有一层含有式(I)所述的化合物。
优选地，结构式(1)所述的化合物所在层为空穴注入层或电子传输层。
本发明的器件有机层的总厚度为1-1000nm，优选1-500nm，更优选5-300nm。
所述有机层可以通过蒸渡或溶液法形成薄膜。
实验结果表明，本发明中的有机电致发光材料，可以有效地降低器件电压，同时提升器件的光电效率，有潜力应用于有机电致发光器件领域。
附图说明
图1为本发明的有机电致发光器件结构图，
其中10代表为玻璃基板，20代表为阳极，30代表为空穴注入层，40代表为空穴传输层，50代表发光层，60代表电子传输层，70代表电子注入层，80代表为阴极。
具体实施方式
下面结合实施例，对本发明做进一步的详细说明。
实施例1
化合物1的合成
中间体1c的合成：
氮气保护下，将化合物1a(3.3g,10.0mmol)(参考专利WO2007/149478合成)、苯并呋喃-2-硼酸酯1b(5.2g,21.0mmol)(参考专利US2009/54454合成)、Pd(PPh3)4(0.58g,0.5mmol)、K2CO3(6.9g,50.0mmol)、四氢呋喃(30mL)和水(5mL)依次加入Schlenk管中。加热至80℃，反应24小时。冷至室温后，将上述反应液加入水中，盐酸调pH至中性，析出浅黄色固体，经正己烷甲醇重结晶得中间体1c(2.5g,产率62％)。
化合物1d的合成：
氮气保护下，将化合物1c(1.5g,3.8mmol)溶于草酰氯(20mL)，滴加DMF(0.5mL)加热至回流反应6小时。减压蒸除草酰氯，将剩余物溶于二氯甲烷中，冷却至0℃，加入三氯化铝(20.0g,15mmol)，逐渐升至室温搅拌24小时。将反应液加入盐酸(2M，20mL)中，搅拌1小时，过滤得紫红色固体(1.1g,产率80％)。
化合物1的合成：
氮气保护下，将化合物1d(1.0g,3.8mmol)和丙二腈(3.3g,50mmol)溶于吡啶(50mL)中，室温搅拌过夜。过滤得紫色固体，甲醇重结晶得化合物1(0.6g,产率34％)。ESI-MS(m/z):461.1(M+1).
实施例2
使用本发明的有机发光材料制备电致发光器件，器件结构见图1。
首先，将透明导电ITO玻璃基板10(上面带有阳极20)依次经：洗涤剂溶液和去离子水，乙醇，丙酮，去离子水洗净，再用氧等离子处理30秒。
然后，在ITO上蒸渡10nm厚的空穴注入层30，空穴注入层由化合物1(3％)与HT1(97％)混合掺杂组成。
然后，蒸渡化合物HT1,形成40nm厚的空穴传输层40。
然后，在空穴传输层上蒸渡30nm厚的发光层50，发光层由Ir(PPy)3(10％)与CBP(90％)混合掺杂组成。
然后，在发光层上蒸渡50nm厚的化合物AlQ3作为电子传输层60。
最后，蒸渡1nm LiF为电子注入层70和100nm Al作为器件阴极80。
对比例
蒸镀10nm厚的HT1作为空穴注入层,其余各层同实施例2中描述,依照相同方法制备有机发光器件。
器件中所述化合物结构式如下：
实施例2及比较例中有机电致发光器件的性能参数如下表：
| 发光器件 | 空穴注入层 | 最大功率效率(lm/W) | 启亮电压(V) | 发光颜色 |
| 实施例2 | 化合物1(3％)/HT1(97％) | 51.2 | 3.2 | 绿光 |
| 对比例 | HT1 | 37.8 | 3.9 | 绿光 |
同等条件下，使用本发明中的化合物掺杂制备的有机电致发光器件的功率效率显著优于比较例，并且可以降低启亮电压，对有机光电器件性能的优化有重要意义。
上述多种实施方案仅作为示例，不用于限制本发明范围。在不偏离本发明精神的前提下，本发明中的多种材料和结构可以用其它材料和结构替代。应当理解，本领域的技术人员无需创造性的劳动就可以根据本发明的思路做出许多修改和变化。因此，技术人员在现有技术基础上通过分析、推理或者部分研究可以得到的技术方案，均应在权利要求书所限制的保护范围内。
Claims (10)
1.有机电致发光材料，为具有式(I)结构的化合物：
其中：
B选自O、S、NR1，R1选自C1-C6的烷基、C3-C40的杂芳基、C6-C40的芳香基；
X1-X4独立地选自N、CR2，R2选自氢、氘、C1-C6的烷基、C3-C40的杂芳基、C6-C40的芳香基。
2.根据权利要求1所述的有机电致发光材料，其中B选自O、S、NR1，R1选自C1-C6的烷基、C3-C9的杂芳基、C6-C14的芳香基；
X1-X4独立地选自N、CR2，R2选自氢、氘、C1-C6的烷基、C3-C9的杂芳基、C6-C14的芳香基。
3.根据权利要求2所述的有机电致发光材料，其中B选自O、S、NR1，R1选自甲基、苯基、甲苯基、萘基、吡啶；
X1-X4独立地选自N、CR2，R2选自氢、氘、C1-C6的烷基、C3-C9的杂芳基、C6-C14的芳香基。
4.根据权利要求3所述的有机电致发光材料，其中B选自O、S、NR1，R1选自甲基、苯基、吡啶基；X1-X4独立地选自N、CH。
5.根据权利要求4所述的有机电致发光材料，其中X1-X4中有0-2个为N，其余的为CH。
6.根据权利要求1所述的有机电致发光材料，为下列化合物：
7.根据权利要求6所述的有机电致发光材料，为下列化合物：
8.有机电致发光器件，包括阴极、阳极和有机层，所述有机层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层、电子传输层中的一层或多层，所述有机层中含有权利要求1-7任一所述的有机电致发光材料。
9.根据权利要求8所述的有机电致发光器件，权利要求1-7任一所述的有机电致发光材料所在层为空穴注入层或电子传输层；权利要求1-7任一所述的有机电致发光材料单独使用，或与其它化合物混合使用。
10.根据权利要求8所述的有机电致发光器件，所述有机层的总厚度为1-1000nm，所述有机层通过蒸渡或溶液法形成薄膜。
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