CN111620897A - 一种化合物及其应用 - Google Patents
一种化合物及其应用 Download PDFInfo
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- CN111620897A CN111620897A CN202010537863.8A CN202010537863A CN111620897A CN 111620897 A CN111620897 A CN 111620897A CN 202010537863 A CN202010537863 A CN 202010537863A CN 111620897 A CN111620897 A CN 111620897A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 239000000463 material Substances 0.000 claims abstract description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 239000010410 layer Substances 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 4
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000000903 blocking effect Effects 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
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 2
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 10
- 238000000605 extraction Methods 0.000 abstract description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052796 boron Inorganic materials 0.000 abstract description 4
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 239000000969 carrier Substances 0.000 abstract description 3
- 230000009477 glass transition Effects 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 239000011159 matrix material Substances 0.000 abstract description 3
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- 238000013508 migration Methods 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 239000002131 composite material Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 10
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- 230000000052 comparative effect Effects 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
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- 239000011368 organic material Substances 0.000 description 3
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- 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
- 125000004429 atom Chemical group 0.000 description 2
- 230000002238 attenuated effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- GHLITDDQOMIBFS-UHFFFAOYSA-H cerium(3+);tricarbonate Chemical compound [Ce+3].[Ce+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O GHLITDDQOMIBFS-UHFFFAOYSA-H 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000009920 chelation Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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Abstract
本发明提供了一种化合物及其应用,该化合物作为发光材料用于OLED器件中,能够提高OLED器件的性能;化合物以含氮和硼的杂环结构为母体,并搭配双极性的取代基,使得化合物具有很强的分子内电荷传输,有效降低效率滚降,提升发光亮度和发光效率EQE,作为电致发光器件中的发光材料,具有较高的三线态能级ET和较大的分子密度,较高玻璃化温度和分子热稳定性,有效提高载流子的平衡迁移,扩宽激子复合区域,有效提高光的取出效率,使得器件的发光效率和寿命有了很大提升,在电致发光器件技术领域中可以得到很好的应用。
Description
技术领域
本发明属于化合物领域,涉及一种化合物及其应用。
背景技术
有机电致发光显示器(以下简称OLED)具有自主发光、低电压直流驱动、全固化、视角宽、重量轻、组成和工艺简单等一系列的优点,与液晶显示器相比,有机电致发光显示器不需要背光源,视角大,功率低,其响应速度可达液晶显示器的1000倍,其制造成本却低于同等分辨率的液晶显示器,因此,有机电致发光器件具有广阔的应用前景。
随着OLED技术在照明和显示两大领域的不断推进,人们对于影响OLED器件性能的高效有机材料的研究更加关注,一个效率好寿命长的有机电致发光器件通常是器件结构与各种有机材料的优化搭配的结果。在最常见的OLED器件结构里,通常包括以下种类的有机材料:空穴注入材料、空穴传输材料、电子传输材料,以及各色的发光材料(染料或者掺杂客体材料)和相应的主体材料等。
根据发光机制,可用于OLED发光层材料主要以下四种:荧光材料、磷光材料、三线态-三线态湮灭(TTA)材料和热活化延迟荧光(TADF)材料。其中,荧光材料的单线激发态S1通过辐射跃迁回到基态S0,根据自旋统计,激子中单线态和三线态激子的比例为1:3,所以荧光材料最大内量子产率不超过25%;依据朗伯发光模式,光取出效率约为20%,因此基于荧光材料的OLED器件的外量子效率EQE不超过5%。磷光材料的三线激发态T1直接辐射衰减到基态S0,由于重原子效应,可以通过自旋偶合作用加强分子内部系间窜越,可以直接利用75%的三线态激子,从而实现在室温下S1和T1共同参与的发射,理论最大内量子产率可达100%;依据朗伯发光模式,光取出效率约为20%,故基于磷光材料的OLED器件的EQE可以达到20%;但是磷光材料基本为Ir、Pt、Os、Re、Ru等重金属配合物,生产成本较高,不利于大规模生产;且在高电流密度下,磷光材料存在严重的效率滚降现象,同时磷光器件的稳定性并不好。2012年Chihaya Adachi教授首先报道了高效的热活化延迟荧光(TADF)器件。热活化延迟荧光材料的单-三线态的能级差较小因而能够通过吸收环境热量经历反向的系间蹿跃过程回到单线态进而发光,器件效率大幅度提升。TADF材料由于不含有金属,成本较低,因而也被誉为新一代发光材料,但是,目前关于热活化延迟荧光材料的相关研究还比较少,材料种类仍然单一,无法满足OLED器件的开发需求。
因此,开发更多种类的高性能的新型TADF材料,是本领域的研究重点。
发明内容
为了开发更多种类、更高性能的TADF材料,本发明的目的之一在于提供一种化合物,所述化合物具有如下所示的结构:
其中,R1和R4独立地选自取代或未取代的C1-C30烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C6-C30芳基氨基中的任意一种,且R1和R4中至少有一项为给电子基;
R2和R3独立地选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种,且R2和R3中至少有一项为吸电子基;
L1、L2、L3和L4独立地选自单键、取代或未取代的C1-C30亚烷基、取代或未取代的C6-C60亚芳基、取代或未取代的C3-C60亚杂芳基中的一种;
Rm和Rn独立地选自取代或未取代的C1-C30烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C60芳基、取代或未取代的C3-C60杂芳基中的一种;
取代的基团选自卤素、C1-C20的烷基、C1-C20的烷氧基、C6-C60的芳基、C3-C60的杂芳基、C6-C60芳基氨基、C3-C60杂芳基氨基中的一种。
本发明在设计化合物时,将N和硼引入同一个分子中作为受体基团,具有较好的吸电子性能,从而使分子的HOMO(最高占有轨道)和LUMO(最低未占有轨道)尽可能分离以达到降低单线态-三线态能级差实现高效反向系间蹿跃的目的,该发明的受体基团具有良好的电子传输能力;由于B原子的螯合作用,使本发明的受体核具有较强的刚性结构,有效地降低了分子震动、转动等造成的非辐射跃迁能量损失,有利于发光效率的提升。
本发明中以含氮和硼的杂环结构为母体,并搭配双极性的取代基,使得化合物具有很强的分子内电荷传输,有效降低效率滚降,提升发光亮度和发光效率EQE,作为电致发光器件中的发光材料,具有较高的三线态能级ET和较大的分子密度,较高玻璃化温度和分子热稳定性,有效提高载流子的平衡迁移,扩宽激子复合区域,有效提高光的取出效率,使得器件的发光效率和寿命有了很大提升,在电致发光器件技术领域中可以得到很好的应用。
本发明中同一个分子中至少存在一个D-A发光子单元,有利于实现HOMO和LUMO的有效分离,优选具有两个D-A发光子单元,具有双重发射核的性质,可以有效地提升振子强度、提高发光效率。
优选地,所述给电子基选自如下基团中的任意一种:
其中,所述X、Y和Z独立地选自碳原子、氮原子、氧原子、硫原子和硅原子中的任意一种;
所述r和s均各自独立地选自0-4的整数,所述g为1-r的整数,所述h为1-s的整数;
所述t选自0-3的整数,所述w为1-t的整数;
所述p选自0-2的整数,所述v为1-p的整数;
所述d选自0-2的整数,所述s为1-d的整数;
所述a和b为0-5的整数,所述e为1-a的整数,f为1-b的整数;
Rg、Rh、Rw、Rq、Rv、Re、Rf独立地选自氢原子、C1-C20烷基、C1-C20烷氧基、C6-C30的芳基、C3-C30杂芳基、C12-C30咔唑基或C12-C30二苯胺基中的一种;
所述取代的基团选自卤素、C1-C20的烷基、C1-C20的烷氧基、C6-C60的芳基、C3-C60的杂芳基、C6-C60芳基氨基、C3-C60杂芳基氨基中的一种;
虚线表示连接位点。
优选地,所述给电子基包括如下基团中的一种:
优选地,所述吸电子基选自取代或未取代的如下基团中的任意一种:
其中,取代的基团选自卤素、氰基、C1-C20的烷基、C1-C20的烷氧基、C6-C60的芳基、C3-C60的杂芳基、C6-C60芳基氨基、C3-C60杂芳基氨基中的一种;
虚线表示连接位点。
优选地,所述吸电子基选自如下基团中的任意一种:
优选地,所述Rm和Rn独立地选自甲基、苯基、萘基或联苯基中的一种。
优选地,所述L1、L2、L3和L4独立地选自单键、亚苯基、亚萘基或亚联苯基中的任意一种。
优选地,所述化合物具有如下所示的结构:
本发明的目的之二在于提供一种发光材料,所述发光材料包括目的之一所述的化合物中的任意一种或至少两种的组合。
本发明提供的化合物的最低单重态S1与最低三重态T1态之间的能极差低于0.30eV,使得反向系间穿越更容易发生,寿命长的三线态激子很容易上转换成单线态激子,单线态激子以光的形式辐射衰减至基态S0,导致高的光致量子产率PLQY,可以有效降低滚降效应,使得器件具有良好的发光性能,可以作为有机光电装置中发光层的掺杂材料、共同掺杂材料或主体材料。
本发明的目的之三在于提供一种OLED器件,所述OLED器件包括阳极、阴极、以及位于阳极和阴极之间的至少一层有机层,所述有机层包括发光层,所述发光层包括目的之二所述的发光材料;
所述有机层还包括空穴传输层、空穴注入层、电子阻挡层、空穴阻挡层、电子传输层和电子注入层中的任意一种或至少两种的组合。
相对于现有技术,本发明具有以下有益效果:
本发明提供的化合物以含氮和硼的杂环结构为母体,并搭配双极性的取代基,使得化合物具有很强的分子内电荷传输,有效降低效率滚降,提升发光亮度和发光效率EQE,作为电致发光器件中的发光材料,具有较高的三线态能级ET和较大的分子密度,较高玻璃化温度和分子热稳定性,有效提高载流子的平衡迁移,扩宽激子复合区域,有效提高光的取出效率,使得器件的发光效率和寿命有了很大提升,在电致发光器件技术领域中可以得到很好的应用。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明提供的化合物示例性的通过如下合成路线制备得到:
其中,R1-R4、L1-L4、Rm和Rn独立地具有与上述相同的限定范围。
实施例1
化合物M1的合成
(1)在250mL三口瓶中依次加入化合物1(10mmol)、化合物2(10mmol)、100mL甲苯、碳酸铈(20mmol)、四(三苯基膦)钯(0.1mmol),然后在氮气氛围下110℃反应过夜。冷却并用二氯甲烷萃取得到有机相,然后通过柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物M1-1。
(2)在250mL三口瓶中依次加入化合物M1-1(10mmol)和五氯化磷(30mmol)在氮气流保护的80ml甲苯中下于100℃加热5h。冷却并用甲苯(50ml)萃取,而后柱层析,得到化合物M1-2。
(3)在250mL三口瓶中依次加入化合物M1-2(20mmol)、化合物E 4.02g(20mmol)、化合物3(10mmol)、100mL甲苯、碳酸铈(30mmol)、四(三苯基膦)钯(0.2mmol),氮气保护下100℃过夜反应。冷却并用二氯甲烷萃取,柱层析(二氯甲烷:正己烷,v:v=1:1)分离纯化,得到化合物M1。
通过质谱分析确定的分子质量为:932.42(计算值为:932.34)。
实施例2
化合物M2的合成
与实施例1的区别仅在于,将化合物1换成摩尔量相同的化合物4,其余制备方法均与实施例1相同。
通过质谱分析确定的化合物M2分子质量为:904.26(计算值为:904.38)。
实施例3
化合物M4的合成
与实施例2的区别仅在于,将化合物3换成摩尔量相同的化合物5,其余制备方法均与实施例1相同。
通过质谱分析确定的分子质量为:1004.25(计算值为:1004.37)。
实施例4
化合物M5的合成
与实施例3的区别仅在于,将化合物1替换为同等摩尔质量的化合物6,其中制备方法均与实施例3相同。
通过质谱分析确定的分子质量为:850.21(计算值为:850.24)。
实施例5
化合物M5的合成
与实施例1的区别仅在于,将化合物1替换为同等摩尔质量的化合物7,把化合物3换成同等摩尔数的化合物8,其中制备方法均与实施,1相同。
通过质谱分析确定的分子质量为:1320.47(计算值为:1320.35)。
应用例1
一种有机电致发光器件的制备方法:
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上真空蒸镀HI-3作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀膜厚为10nm;
在空穴注入层之上真空蒸镀HT-29作为器件的空穴传输层,蒸镀速率为0.1nm/s,蒸镀总膜厚为50nm;
在空穴传输层之上真空蒸镀器件的发光层,发光层包括主体材料和染料材料,利用多源共蒸的方法,调节主体材料TDH-21蒸镀速率为0.1nm/s,染料M1蒸镀速率10%比例设定,蒸镀总膜厚为30nm;
在发光层之上真空蒸镀器件的电子传输层材料ET-53,其蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm;
在电子传输层(ETL)上真空蒸镀厚度为0.5nm的LiF作为电子注入层,厚度为150nm的Al层作为器件的阴极。
使其具有如下结构:
ITO/HI-3(10nm)/HT-29(50nm)/TDH-21:10%M1(30nm)/ET-53(30nm)/LiF(0.5nm)/Al(150nm)。
应用例2-6
与应用例1的区别仅在于,将应用例1中的化合物M1依次替换为M2、M4、M5、M12以及M14,得到应用例2-6。
对比例1
与应用例1的区别仅在于,将应用例1中的M1替换为BczVBi。
性能测试:在同样亮度下,使用数字源表及亮度计测定实施例以及对比例中制备得到的有机电致发光器件的开启电压以及器件的寿命。具体而言,以每秒0.1V的速率提升电压,测定当有机电致发光器件的亮度达到1cd/m2时的电压即开启电压,同时测出此时的电流密度;亮度与电流密度的比值即为电流效率,再根据光谱数据计算出外量子效率,测试结果见表1:
表1
器件编号 | 最大亮度/cd/m<sup>2</sup> | 开启电压/V | 最大外量子效率/% |
应用例1 | 23853 | 3.6 | 16.8 |
应用例2 | 25649 | 3.5 | 14.3 |
应用例3 | 32415 | 3.7 | 16.0 |
应用例4 | 28996 | 3.8 | 15.4 |
应用例5 | 27507 | 3.5 | 16.6 |
应用例6 | 33078 | 3.9 | 15.3 |
对比例1 | 2450 | 4.7 | 2.5 |
由表1可知,本发明基于实施例1-6制备的化合物作为发光层客体材料制备的OLED显示面板具有较好的器件性能,不含有重金属且最大外量子效率均超过14%,明显高于对比例的值,是性能良好的发光材料。
申请人声明,以上所述仅为本发明的具体实施方式,但本发明的保护范围并不局限于此,所属技术领域的技术人员应该明了,任何属于本技术领域的技术人员在本发明揭露的技术范围内,可轻易想到的变化或替换,均落在本发明的保护范围和公开范围之内。
Claims (10)
1.一种化合物,其特征在于,所述化合物具有如下所示的结构:
其中,R1和R4独立地选自取代或未取代的C1-C30烷基、取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基、取代或未取代的C6-C30芳基氨基中的任意一种,且R1和R4中至少有一项为给电子基;
R2和R3独立地选自取代或未取代的C6-C30芳基、取代或未取代的C3-C30杂芳基中的任意一种,且R2和R3中至少有一项为吸电子基;
L1、L2、L3和L4独立地选自单键、取代或未取代的C1-C30亚烷基、取代或未取代的C6-C60亚芳基、取代或未取代的C3-C60亚杂芳基中的一种;
Rm和Rn独立地选自取代或未取代的C1-C30烷基、取代或未取代的C1-C30烷氧基、取代或未取代的C6-C60芳基、取代或未取代的C3-C60杂芳基中的一种;
取代的基团选自卤素、C1-C20的烷基、C1-C20的烷氧基、C6-C60的芳基、C3-C60的杂芳基、C6-C60芳基氨基、C3-C60杂芳基氨基中的一种。
2.根据权利要求1所述的化合物,其特征在于,所述给电子基选自如下基团中的任意一种:
其中,所述X、Y和Z独立地选自碳原子、氮原子、氧原子、硫原子和硅原子中的任意一种;
所述r和s均各自独立地选自0-4的整数,所述g为1-r的整数,所述h为1-s的整数;
所述t选自0-3的整数,所述w为1-t的整数;
所述p选自0-2的整数,所述v为1-p的整数;
所述d选自0-2的整数,所述s为1-d的整数;
所述a和b为0-5的整数,所述e为1-a的整数,f为1-b的整数;
Rg、Rh、Rw、Rq、Rv、Re、Rf独立地选自氢原子、C1-C20烷基、C1-C20烷氧基、C6-C30的芳基、C3-C30杂芳基、C12-C30咔唑基或C12-C30二苯胺基中的一种;
所述取代的基团选自卤素、C1-C20的烷基、C1-C20的烷氧基、C6-C60的芳基、C3-C60的杂芳基、C6-C60芳基氨基、C3-C60杂芳基氨基中的一种;
虚线表示连接位点。
6.根据权利要求1所述的化合物,其特征在于,所述Rm和Rn独立地选自甲基、苯基、萘基或联苯基中的一种。
7.根据权利要求1所述的化合物,其特征在于,所述L1、L2、L3和L4独立地选自单键、亚苯基、亚萘基或亚联苯基中的任意一种。
9.一种发光材料,其特征在于,所述发光材料包括权利要求1-8任一项所述的化合物中的任意一种或至少两种的组合。
10.一种OLED器件,其特征在于,所述OLED器件包括阳极、阴极、以及位于阳极和阴极之间的至少一层有机层,所述有机层包括发光层,所述发光层包括权利要求9所述的发光材料;
所述有机层还包括空穴传输层、空穴注入层、电子阻挡层、空穴阻挡层、电子传输层和电子注入层中的任意一种或至少两种的组合。
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102899027A (zh) * | 2012-04-12 | 2013-01-30 | 杭州师范大学 | 一类含硼发光材料及其制备方法与应用 |
CN111377952A (zh) * | 2018-12-28 | 2020-07-07 | 北京鼎材科技有限公司 | 一种化合物及其应用、包含其的有机电致发光器件 |
CN111662312A (zh) * | 2020-06-08 | 2020-09-15 | 武汉天马微电子有限公司 | 一种化合物、热激活延迟荧光材料及其应用 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102899027A (zh) * | 2012-04-12 | 2013-01-30 | 杭州师范大学 | 一类含硼发光材料及其制备方法与应用 |
CN111377952A (zh) * | 2018-12-28 | 2020-07-07 | 北京鼎材科技有限公司 | 一种化合物及其应用、包含其的有机电致发光器件 |
CN111662312A (zh) * | 2020-06-08 | 2020-09-15 | 武汉天马微电子有限公司 | 一种化合物、热激活延迟荧光材料及其应用 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113173943A (zh) * | 2021-05-10 | 2021-07-27 | 清华大学 | 一种稠环化合物及其应用以及包含其的有机电致发光器件 |
WO2022237668A1 (zh) * | 2021-05-10 | 2022-11-17 | 清华大学 | 一种稠环化合物及其应用以及包含其的有机电致发光器件 |
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