CN112574254A - 一种用于有机发光的化合物及其应用 - Google Patents
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- 238000004020 luminiscence type Methods 0.000 title abstract description 6
- 239000000463 material Substances 0.000 claims abstract description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims abstract description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
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- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 1
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- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
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Abstract
本发明涉及一种用于有机发光的化合物,所述化合物的结构如式(I)所示;其中,R1‑R3分别独立地选自氢、取代或未取代的芳基基团、取代或未取代的杂芳基基团、取代或未取代的烷基基团;L选自取代或未取代的苯基,取代或未取代的杂芳基;Ar1和Ar2分别独立地选自取代或未取代的苯基、萘基、蒽基。本发明的一种用于有机发光的化合物可用作电子传输材料,其不仅具较高的稳定性,也具有高电荷转移能力和高玻璃化转变温度。
Description
技术领域
本发明涉及光电材料领域,尤其涉及一种用于有机发光的化合物及其应用。
背景技术
有机电致发光元件具有以空穴传输层和电子传输层夹持含有发光材料的发光层,进而在该夹层结构的两外侧安装阳极和阴极而形成的结构。有机电致发光元件是利用由注入发光层中的空穴及电子的再键合而产生的激子失活时放出光(荧光或磷光)的元件,被应用于显示器等。
为了使有机发光器件具有足够的优异特性,形成有机材料层的材料,例如空穴注入材料、空穴传输材料、发光材料、电子传输材料、电子注入材料等首先需要由稳定且有效的材料来支撑,然而,目前用于有机发光器件的有机材料层的稳定且有效的材料的开发仍然不足。因此,需要持续开发新材料,而且需要这些开发的材料还能应用于上述的其他有机电子器件。
发明内容
本发明的目的是针对现有技术中的不足,提供一种用于有机发光的化合物。
为实现上述目的,本发明采取的技术方案是:
本发明的第一方面是提供一种用于有机发光的化合物,所述化合物的结构如式(I)所示:
其中,R1-R3分别独立地选自氢、取代或未取代的芳基基团、取代或未取代的杂芳基基团、取代或未取代的烷基基团;L选自取代或未取代的苯基,取代或未取代的杂芳基;Ar1和Ar2分别独立地选自取代或未取代的苯基、萘基、蒽基。
优选地,R1-R3分别独立地选自氢、取代或未取代的C6-C60的芳基基团、取代或未取代的C6-C60的杂芳基基团、取代或未取代的C1-C50的烷基基团。
优选地,所述未取代的C6-C60的芳基基团包括:苯基、萘基、蒽基、菲基、醌基、芴基、螺芴基。
优选地,所述未取代的C6-C60的杂芳基基团包括:呋喃基、噻吩基、吡咯基、咪唑基、恶唑基、噻唑基、苯并呋喃基、苯并咪唑基、喹啉基、异喹啉基。
优选地,所述未取代的C1-C50的烷基基团包括:甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、己基、环丙基、环丁基、环戊基、环己基。
优选地,L,Ar1和Ar2均为苯基。
优选地,所述化合物的结构如下所示:
本发明的第二方面是提供一种电子传输材料,包括如上述的化合物。
本发明的第三方面是提供一种电子传输层,包括如上述的电子传输材料。
本发明的第四方面是提供一种OLED装置,包括如上述的电子传输层。
本发明采用以上技术方案,与现有技术相比,具有如下技术效果:
本发明的一种用于有机发光的化合物可用作电子传输材料,其不仅具较高的稳定性,也具有高电荷转移能力和高玻璃化转变温度。
具体实施方式
下面对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有作出创造性劳动的前提下所获得的所有其他实施例,都属于本发明保护的范围。
需要说明的是,在不冲突的情况下,本发明中的实施例及实施例中的特征可以相互组合。
下面结合具体实施例对本发明作进一步说明,但不作为本发明的限定。
实施例1
本实施例提供一种用于有机发光的化合物,其结构式如下所示:
其合成方法如下所示:
(a)将85mmol化合物1溶于100mL四氢呋喃中,然后将混合物冷却至78℃。将37mL93mmol的n-BuLi缓慢滴入其中,然后将得到的混合物搅拌30分钟。将76mmol的化合物2缓慢滴入其中,将混合物搅拌3小时并加热至常温,然后将100mL的水加入其中并采用四氢呋喃萃取,得到的有机层浓缩并用己烷重结晶得到化合物3;
(b)将58mmol的化合物3溶于200mL三氯甲烷中,将20mL过氧化氢溶液加入其中,然后将得到的混合物搅拌12小时。向其中加入MgSO4并搅拌混合物以除去水,对得到的混合物进行过滤、浓缩并以己烷重结晶得到化合物4;
(c)在保护气体下,将50mmol的化合物5、25mmol的Pd(OAc)2、118mmol的CuI、200mmol的化合物6悬浮在300mL的脱气DMF中,并且将所述反应化合物在140℃的回流下加热24小时。所述混合物冷却后,在真空中除去溶剂,将残渣溶解在二氯甲烷中,并添加水。然后分离出有机相并通过硅胶过滤对产物进行提纯,最终得到得到化合物7;
(d)将40mmol化合物7、47mmol联硼酸频那醇酯和118mmol乙酸钾溶于150ml二氧六环中,将混合物加热至50℃,将0.4mmol Pd(DBA)2和0.8mmol P(Cy)3加入其中,并将得到的混合物边搅拌边加热12小时。将反应溶液冷却至室温,将100mL蒸馏水加入其中,并用二氯甲烷萃取混合物,再将有机层浓缩并用乙醇重结晶得到化合物8;
(e)将22.4mmol化合物8和22.4mmol化合物4加热至完全溶于200mL四氢呋喃中,然后将100mL 2M的碳酸钾水溶液加入所述溶液中,向其中加入0.22mmol Pd(PPh3)4,并将混合物搅拌12小时。将混合物冷却至常温,移除水层,并过滤制得的固体。经过滤的固体用四氢呋喃和丙酮重结晶得到化合物A。
化合物A的产率为86%。表征数据:熔点(DSC)283℃,纯度99.9%;1H NMR(400MHz,CDCl3)δ(ppm):7.70(s,2H),7.50-7.32(m,6H),7.30-7.22(m,23H)。
实施例2
本实施例提供一种用于有机发光的化合物,其结构式如下所示:
其合成方法与实施例1类似,仅需将原料进行相应的替换即可。
化合物B的产率为78%。表征数据:熔点(DSC)278℃,纯度99.9%;1H NMR(400MHz,CDCl3)δ(ppm):7.70(s,2H),7.67-7.50(m,6H),7.38-7.30(m,15H),3.77-1.51(m,10H)。
实施例3
本实施例提供一种用于有机发光的化合物,其结构式如下所示:
其合成方法与实施例1类似,仅需将原料进行相应的替换即可。
化合物C的产率为88%。表征数据:熔点(DSC)276℃,纯度99.9%;1H NMR(400MHz,CDCl3)δ(ppm):7.70(s,2H),7.52-7.48(m,2H),7.34-7.28(m,22H),2.59-1.24(m,5H)。
应用例
提供一种OLED器件,其由下至上依次包括阳极、空穴注入层、空穴传输层、发光层、电子传输层和阴极;所述电子传输层包括主体材料和客体材料,所述主体材料为实施例制备得到的化合物或对比的材料(BPhen)。
各层的组成材料如下:
阳极:ITO(氧化铟锡),厚度为80nm;
空穴注入层:主体材料NPB,客体材料F4-TCNQ,客体材料的摩尔百分含量为5%;空穴注入层的厚度为10nm;
空穴传输层:材料NPB,厚度为130nm;
发光层:主体材料TCTA,客体材料Ir(ppy)3,客体材料的摩尔百分含量为7%;厚度为20nm;
电子传输层:厚度35nm,主体材料和客体材料以及其摩尔百分含量如表1所示;
阴极:Mg/Ag,厚度20nm。
表1
序号 | 电子传输层的主体和客体材料 |
应用例1 | 化合物A(50%):LiQ(50%) |
应用例2 | 化合物B(50%):LiQ(50%) |
应用例3 | 化合物C(50%):LiQ(50%) |
对比例1 | BPhen(50%):LiQ(50%) |
上述材料中简称所对应的结构式如下:
器件性能测试:
将应用例和对比例提供的OLED器件进行发光效率的测试,测试项目包括效率、驱动电压(V)和寿命(LT95,亮度衰减到95%的时间)。
其中,器件光电性能数据在电流密度20mA/cm2条件下测得,寿命(LT95)数据在电流密度35mA/cm2条件下计算得到。
性能测试结果如下表所示:
表2
性能证实,本发明材料高度适合用作OLED器件中的电子传输材料,并且具有很好的电子传输性能。与对比例相比,所选用于器件实施例中的材料具有更高的效率(不低于80Cd/A),更低的电压(不高于4.1V),更长的寿命(不低于86h)。
以上所述仅为本发明较佳的实施例,并非因此限制本发明的实施方式及保护范围,对于本领域技术人员而言,应当能够意识到凡运用本发明说明书内容所作出的等同替换和显而易见的变化所得到的方案,均应当包含在本发明的保护范围内。
Claims (10)
2.根据权利要求1所述的化合物,其特征在于,R1-R3分别独立地选自氢、取代或未取代的C6-C60的芳基基团、取代或未取代的C6-C60的杂芳基基团、取代或未取代的C1-C50的烷基基团。
3.根据权利要求1所述的化合物,其特征在于,所述未取代的C6-C60的芳基基团包括:苯基、萘基、蒽基、菲基、醌基、芴基、螺芴基。
4.根据权利要求1所述的化合物,其特征在于,所述未取代的C6-C60的杂芳基基团包括:呋喃基、噻吩基、吡咯基、咪唑基、恶唑基、噻唑基、苯并呋喃基、苯并咪唑基、喹啉基、异喹啉基。
5.根据权利要求1所述的化合物,其特征在于,所述未取代的C1-C50的烷基基团包括:甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、己基、环丙基、环丁基、环戊基、环己基。
6.根据权利要求1所述的化合物,其特征在于,L,Ar1和Ar2均为苯基。
8.一种电子传输材料,其特征在于,包括如权利要求1-7任一项所述的化合物。
9.一种电子传输层,其特征在于,包括如权利要求8所述的电子传输材料。
10.一种OLED装置,其特征在于,包括如权利要求9所述的电子传输层。
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