CN107057684A - 一种基于双极磷光衍生物的有机发光材料及其有机发光器件 - Google Patents
一种基于双极磷光衍生物的有机发光材料及其有机发光器件 Download PDFInfo
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- CN107057684A CN107057684A CN201710255040.4A CN201710255040A CN107057684A CN 107057684 A CN107057684 A CN 107057684A CN 201710255040 A CN201710255040 A CN 201710255040A CN 107057684 A CN107057684 A CN 107057684A
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- 239000011368 organic material Substances 0.000 title claims abstract description 21
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- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 238000006467 substitution reaction Methods 0.000 claims description 12
- -1 aryl phosphines Chemical class 0.000 claims description 9
- 150000002894 organic compounds Chemical class 0.000 claims description 9
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- LDZIPAUZQBAFFA-UHFFFAOYSA-N c(cc1)ccc1-c(cc1N(c2c3ccc(-c4ccccc4)c2)c2nc4ccccc4cn2)ccc1N3c1nc(cccc2)c2cn1 Chemical compound c(cc1)ccc1-c(cc1N(c2c3ccc(-c4ccccc4)c2)c2nc4ccccc4cn2)ccc1N3c1nc(cccc2)c2cn1 LDZIPAUZQBAFFA-UHFFFAOYSA-N 0.000 description 1
- QVISVCHDMNAGJH-UHFFFAOYSA-N c1cc2cccc(C(C3=CN4)=CC=CC3=NC4N(c3c4cccc3)c3ccccc3N4c3nc4ccccc4cn3)c2cc1 Chemical compound c1cc2cccc(C(C3=CN4)=CC=CC3=NC4N(c3c4cccc3)c3ccccc3N4c3nc4ccccc4cn3)c2cc1 QVISVCHDMNAGJH-UHFFFAOYSA-N 0.000 description 1
- AFMBJKPOFGGUIY-UHFFFAOYSA-N c1ccc2[s]c3cc(-c(cc4)cc(C(C5c6c7cccc6)C5c5nc(cccc6)c6cn5)c4N7c4ncc(cccc5)c5n4)ccc3c2c1 Chemical compound c1ccc2[s]c3cc(-c(cc4)cc(C(C5c6c7cccc6)C5c5nc(cccc6)c6cn5)c4N7c4ncc(cccc5)c5n4)ccc3c2c1 AFMBJKPOFGGUIY-UHFFFAOYSA-N 0.000 description 1
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- 229910052805 deuterium Inorganic materials 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 230000036961 partial effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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Abstract
本发明提供一种基于双极磷光衍生物的有机发光材料及其有机发光器件,属于有机光电材料技术领域。解决现有技术中有机光电材料发光效率低、使用寿命短等发光性能差的技术问题。本发明以二氢吩嗪基团连接喹唑啉基团为核,使得结构中兼有得电子与失电子基团,从而得到一种新颖的电子与空穴双极传输型材料。与现有技术相比,本发明的基于双极磷光衍生物的有机发光器件,发光效率最高可达19.7cd/A,发光寿命为210h@100mA/cm2,是一种优异的OLED材料。
Description
技术领域
本发明涉及有机光电材料技术领域,具体涉及一种基于双极磷光衍生物的有机发光材料及其有机发光器件。
背景技术
有机电致发光是指有机材料在电场作用下,受到电流和电场的激发而发光的现象。在过去三十年里,有机电致发光技术迅猛发展,其部分性能已经接近甚至超越了无机半导体材料,有望在大屏幕及超大屏幕显示领域挑战传统的CRT、LCD技术。
当前在OLED的研究中,器件一般采用三明治结构,其中包含空穴注入、空穴传输层、发光层与电子注入、电子传输层等。但是在有机光电材料中空穴传输性能占主导,如何平衡器件的电子与空穴传输速率是发展的关键。另一方面,所有的空穴或电子传输型主体材料掺杂客体发光体形成发光层,激子复合区域会选择性地偏向某一边,从而导致器件效率与光色的改变,甚为严重的可能会引起三重态之间的能量淬灭,导致高亮度下效率滚降严重。双极磷光化合物可以通过在化合物的结构中同时引入电子与空穴传输基团,在保证三线态能级和热稳定性的基础上,进一步调整期间的激子复合区域。一般来说,对于双极传输型主体材料要满足以下几点:一、有利于电子和空穴的注入和传输,二、良好的热稳定性和成膜性,三、与相邻的活化层有很好的能级匹配,四、具有比掺杂客体更高的三线态能级。由于技术的原因,目前同时具有以上特征的双极传输型材料还较少,提高发光效率是开发制备双极磷光衍生物的重要着眼点之一。
发明内容
有鉴于此,本发明的目的在于提供一种基于双极磷光衍生物的有机发光材料及其有机发光器件,本发明化合物以二氢吩嗪基团直接连接喹唑啉为核,得到一种基于磷光衍生物的电子与空穴双极传输型材料。采用本发明所述基于双极磷光衍生物制备的有机发光器件,具有更高的发光效率,及更长的发光寿命。
本发明首先提供了一种基于双极磷光衍生物的有机发光材料,具有如式A所示的结构式:
其中,R1~R4独立的选自氢、C1-C4的烷基、取代或未取代的C6-C50芳基、取代或未取代的C7-C50芳烷基、取代或未取代的C6-C50芳胺、取代或未取代的C6-C50芳基膦、取代或未取代的C3-C50杂芳基中的任意一种;
R5~R8独立的选自氢、取代或未取代的C6-C50芳基、取代或未取代的C7-C50芳烷基、取代或未取代的C3-C50杂芳基中的任意一种。
优选的,所述的R1~R4独立的选自氢、C1-C4的烷基、取代或未取代的C6-C30芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳基膦、取代或未取代的C3-C30杂芳基中的任意一种;
R5~R8独立的选自氢、取代或未取代的C6-C30芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C3-C30杂芳基中的任意一种。
优选的,所述基于双极磷光衍生物的有机发光材料,选自如下结构中的任意一种:
本发明还提供一种基于双极磷光衍生物的有机发光器件,包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层,至少一个有机化合物层包含至少一种所述的基于双极磷光衍生物的有机发光材料。
优选的,所述有机化合物层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。
本发明的有益效果:
本发明提供一种基于双极磷光衍生物的有机发光材料及其有机发光器件,本发明以二氢吩嗪基团连接喹唑啉基团为核,使得结构中兼有得电子与失电子基团,从而得到一种新颖的电子与空穴双极传输型材料。
与现有技术相比,本发明的基于双极磷光衍生物的有机发光器件,发光效率最高可达19.7cd/A,发光寿命为210h@100mA/cm2,是一种优异的OLED材料。
具体实施方式
下面将结合本发明实施例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做出创造性劳动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。
本发明首先提供一种基于双极磷光衍生物的有机发光材料,具有如式A所示的结构式:
其中,R1~R4独立的选自氢、C1-C4的烷基、取代或未取代的C6-C50芳基、取代或未取代的C7-C50芳烷基、取代或未取代的C6-C50芳胺、取代或未取代的C6-C50芳基膦、取代或未取代的C3-C50杂芳基中的任意一种,优选独立的选自氢、C1-C4的烷基、取代或未取代的C6-C30芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳基膦、取代或未取代的C3-C30杂芳基中的任意一种。
R5~R8独立的选自氢、取代或未取代的C6-C50芳基、取代或未取代的C7-C50芳烷基、取代或未取代的C3-C50杂芳基中的任意一种,优选独立的选自氢、取代或未取代的C6-C30芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C3-C30杂芳基中的任意一种。
按照本发明,所述取代的芳基、取代的芳烷基、取代的芳胺、取代的芳基膦、取代的杂芳基中,所述取代基可选自氘、C1~C4烷基、C6-C18芳基、C6-C18芳氧基或C6-C18芳硫基,所述取代基的个数优选为1~3个。所述杂芳基中的杂原子优选为O、S、N或Si。
作为举例,没有特别限定,本发明所述基于双极磷光衍生物的有机发光材料,优选选自如下结构中的任意一种:
本发明所述基于双极磷光衍生物的有机发光材料的制备方法,包括将式B-1所示的中间体化合物通过如下路线反应生成式A所示的基于双极磷光衍生物的有机发光材料:
其中,R1~R4独立的选自氢、C1-C4的烷基、取代或未取代的C6-C50芳基、取代或未取代的C7-C50芳烷基、取代或未取代的C6-C50芳胺、取代或未取代的C6-C50芳基膦、取代或未取代的C3-C50杂芳基中的任意一种;R5~R8独立的选自氢、取代或未取代的C6-C50芳基、取代或未取代的C7-C50芳烷基、取代或未取代的C3-C50杂芳基中的任意一种。
本发明对上述各类反应的反应条件没有特殊要求,以本领域技术人员熟知的此类反应的常规条件即可。本发明对上述各类反应中所采用的原料的来源没有特别的限制,可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。其中,所述R1-R8的选择同上所述,在此不再赘述。
本发明还提供一种基于双极磷光衍生物的有机发光器件,所述有机发光器件为本领域技术人员所熟知的有机发光器件即可。本发明所述有机发光器件包括第一电极、第二电极和置于两电极之间的一个或多个有机化合物层,至少一个有机化合物层包含至少一种本发明所述的基于双极磷光衍生物的有机发光材料。所述有机化合物层优选包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层与电子注入层中的至少一层,优选所述的发光层中含有本发明所述的基于双极磷光衍生物的有机发光材料。
实施例1:化合物1的制备
Step1,取100mmol的吩嗪衍生物,加入220mmol的2-氯喹唑啉,300mmol叔丁醇钾,1mmol Pd2(dba)3,甲苯,氩气置换三次,加入2mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品76mmol化合物1。
实施例2:化合物2的合成
Step1,取100mmol的2,5-二氯喹唑啉,加入105mmol的苯硼酸,300mmol碳酸钠,1mmol四三苯基磷钯,甲苯,乙醇,水的混合溶剂,氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品81mmol化合物2-1。
Step2,取100mmol的吩嗪衍生物,加入115mmol的2-氯喹唑啉,300mmol叔丁醇钾,1mmol Pd2(dba)3,甲苯,氩气置换三次,加入2mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品76mmol化合物2-2。
Step3,取76mmol的2-2,加入81mmol的2-1,240mmol叔丁醇钾,0.8mmol Pd2(dba)3,甲苯,氩气置换三次,加入1.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品59mmol化合物2。
实施例3:化合物17的合成
Step1,取100mmol的溴代吩嗪衍生物,加入105mmol的苯硼酸,300mmol碳酸钠,1mmol四三苯基磷钯,甲苯,乙醇,水的混合溶剂,氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品81mmol化合物17-1
Step2,取81mmol的17-1,加入200mmol的2-氯喹唑啉,240mmol叔丁醇钾,0.8mmolPd2(dba)3,甲苯,氩气置换三次,加入1.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品66mmol化合物17。
实施例4:化合物18的合成
Step1,取100mmol的溴代吩嗪衍生物,加入210mmol的苯硼酸,300mmol碳酸钠,1mmol四三苯基磷钯,甲苯,乙醇,水的混合溶剂,氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品74mmol化合物18-1。
Step2,取74mmol 18-1,加入160mmol的2-氯喹唑啉,210mmol叔丁醇钾,0.8mmolPd2(dba)3,甲苯,氩气置换三次,加入1.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品55mmol化合物18。
实施例5:化合物20的合成
Step1,取100mmol的溴代吩嗪衍生物,加入115mmol的吡啶-3-硼酸,300mmol碳酸钠,1mmol四三苯基磷钯,甲苯,乙醇,水的混合溶剂,氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品61mmol化合物20-1。
Step2,取61mmol的20-1,加入150mmol的2-氯喹唑啉,180mmol叔丁醇钾,0.6mmolPd2(dba)3,甲苯,氩气置换三次,加入1.2mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品46mmol化合物20。
实施例6:化合物22的合成
Step1,100mmol的溴代吩嗪衍生物,加入100mmol的咔唑,300mmol叔丁醇钾,1mmolPd2(dba)3,甲苯,氩气置换三次,加入2mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品82mmol化合物22-1。
Step2,取82mmol的22-1,加入180mmol的2-氯喹唑啉,240mmol叔丁醇钾,0.8mmolPd2(dba)3,甲苯,氩气置换三次,加入1.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品69mmol化合物22。
实施例7:化合物26的合成
Step1,100mmol的溴代吩嗪衍生物,加入无水四氢呋喃,冷却到-78摄氏度,加入正丁基锂0.6mol,在此温度下搅拌2h。加入110mmol化合物二苯基氯化磷,逐渐升温到室温,反应过夜。次日,将反应液倒入水中,有白色固体析出,过滤。粗品用甲苯重结晶,得到74mmol化合物26-1。
Step2,取74mmol的26-1,加入160mmol的2-氯喹唑啉,240mmol叔丁醇钾,0.8mmolPd2(dba)3,甲苯,氩气置换三次,加入1.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品52mmol化合物26。
实施例8:化合物31的合成
Step1,取100mmol的溴代吩嗪衍生物,加入115mmol的芴硼酸,300mmol碳酸钠,1mmol四三苯基磷钯,甲苯,乙醇,水的混合溶剂,氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品80mmol化合物31-1。
Step2,取80mmol的31-1,加入170mmol的2-氯喹唑啉,240mmol叔丁醇钾,0.8mmolPd2(dba)3,甲苯,氩气置换三次,加入1.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品65mmol化合物31。
实施例9:化合物37的合成
Step1,100mmol的溴代吩嗪衍生物,加入100mmol的咔唑衍生物,300mmol叔丁醇钾,1mmol Pd2(dba)3,甲苯,氩气置换三次,加入2mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品71mmol化合物37-1。
Step2,取71mmol37-1,加入160mmol的2-氯喹唑啉,210mmol叔丁醇钾,0.7mmolPd2(dba)3,甲苯,氩气置换三次,加入1.4mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品49mmol化合物37。
实施例10:化合物38的合成
Step1,100mmol的溴代吩嗪衍生物,加入100mmol的苯并吡啶衍生物,300mmol叔丁醇钾,1mmol Pd2(dba)3,甲苯,氩气置换三次,加入2mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品82mmol化合物38-1。
Step2,取82mmol的38-1,加入180mmol的2-氯喹唑啉,240mmol叔丁醇钾,0.8mmolPd2(dba)3,甲苯,氩气置换三次,加入1.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品69mmol化合物38。
实施例11:化合物46的合成
Step1,取100mmol的溴代吩嗪衍生物,加入110mmol的硼酸,300mmol碳酸钠,1mmol四三苯基磷钯,甲苯,乙醇,水的混合溶剂,氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品70mmol化合物46-1。
Step2,取70mmol的46-1,加入160mmol的2-氯喹唑啉,210mmol叔丁醇钾,0.7mmolPd2(dba)3,甲苯,氩气置换三次,加入1.7mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品55mmol化合物46。
实施例12:化合物52的合成
Step1,取100mmol的2,8-二氯喹唑啉,加入105mmol的对异丙基苯硼酸,300mmol碳酸钠,1mmol四三苯基磷钯,甲苯,乙醇,水的混合溶剂,氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品79mmol化合物52-1。
Step2,取30mmol的52-1,加入79mmol的喹唑啉氯代物,90mmol叔丁醇钾,0.3mmolPd2(dba)3,甲苯,氩气置换三次,加入0.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品19mmol化合物52。
实施例13:化合物54的合成
Step1,取100mmol的2,8-二氯喹唑啉,加入105mmol的苯硼酸,300mmol碳酸钠,1mmol四三苯基磷钯,甲苯,乙醇,水的混合溶剂,氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品81mmol化合物54-1。
Step2,取100mmol的54-1,加入115mmol的2-氯喹唑啉,300mmol叔丁醇钾,1mmolPd2(dba)3,甲苯,氩气置换三次,加入2mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品76mmol化合物54-2。
Step3,取76mmol 54-2,加入81mmol的2-氯-5-苯基喹唑啉,240mmol叔丁醇钾,0.8mmol Pd2(dba)3,甲苯,氩气置换三次,加入1.6mmol三叔丁基膦,再次氩气置换三次,回流温度下反应10h,粗产品过硅胶柱,得到产品59mmol化合物54。
本发明实施例制备得到的基于双极磷光衍生物有机发光材料的FD-MS值见表1所示。
表1本发明实施例制备的化合物FD-MS值
化合物 | FD-MS |
1 | M/z:438.44,C28H18N6(438.16) |
2 | M/z:514.57,C34H22N6(514.19) |
17 | M/z:514.35,C34H22N6(514.19) |
18 | M/z:590.64,C40H26N6(590.22) |
20 | M/z:515.37,C33H21N7(515.19) |
22 | M/z:603.20,C40H25N7(603.22) |
26 | M/z:622.08,C40H27N6P(622.20) |
31 | M/z:630.47,C43H30N6(630.25) |
37 | M/z:709.55,C46H27N7S(709.20) |
38 | M/z:617.11,C41H27N7(617.23) |
46 | M/z:646.28,C42H30N6Si(646.23) |
52 | M/z:522.48,C34H30N6(522.25) |
54 | M/z:570.49,C38H30N6(570.25) |
对比应用实施例1:
取ITO透明玻璃为阳极,超声清洗后干燥至于真空腔中,抽真空至5×10-5Pa,在上述阳极基板上真空蒸镀NPB作为空穴传输层,蒸镀速率为0.1nm/s,蒸镀厚度为70nm。在空穴传输层上真空蒸镀mCP/FIrpic作为发光层,掺杂浓度为10wt%,蒸镀速率为0.005nm/s,蒸镀厚度为30nm。在发光层上真空蒸镀Alq3作为电子传输层,蒸镀速率为0.01nm/s,蒸镀厚度为50nm。在电子传输层上真空蒸镀Al层作为阴极,厚度为200nm。
应用实例1:
取ITO透明玻璃为阳极,超声清洗后干燥至于真空腔中,抽真空至5×10-5Pa,在上述阳极基板上真空蒸镀NPB作为空穴传输层,蒸镀速率为0.1nm/s,蒸镀厚度为70nm。在空穴传输层上真空蒸镀化合物1/FIrpic作为发光层,掺杂浓度为10wt%,蒸镀速率为0.005nm/s,蒸镀厚度为30nm。在发光层上真空蒸镀Alq3作为电子传输层,蒸镀速率为0.01nm/s,蒸镀厚度为50nm。在电子传输层上真空蒸镀Al层作为阴极,厚度为200nm。
应用实例2:
将应用实施例1中的化合物1换成化合物2。测量该器件的发光性能,结果见表2。
应用实例3:
将应用实施例1中的化合物1换成化合物17。测量该器件的发光性能,结果见表2。
应用实例4:
将应用实施例1中的化合物1换成化合物18。测量该器件的发光性能,结果见表2。
应用实例5:
将应用实施例1中的化合物1换成化合物20。测量该器件的发光性能,结果见表2。
应用实例6:
将应用实施例1中的化合物1换成化合物22。测量该器件的发光性能,结果见表2。
应用实例7:
将应用实施例1中的化合物1换成化合物26。测量该器件的发光性能,结果见表2。
应用实例8:
将应用实施例1中的化合物1换成化合物31。测量该器件的发光性能,结果见表2。
应用实例9:
将应用实施例1中的化合物1换成化合物37。测量该器件的发光性能,结果见表2。
应用实例10:
将应用实施例1中的化合物1换成化合物38。测量该器件的发光性能,结果见表2。
应用实例11:
将应用实施例1中的化合物1换成化合物46。测量该器件的发光性能,结果见表2。
应用实例12:
将应用实施例1中的化合物1换成化合物52。测量该器件的发光性能,结果见表2。
应用实例13:
将应用实施例1中的化合物1换成化合物54。测量该器件的发光性能,结果见表2。
测量实施例1:对比样品以及样品的发光性能
对比样品以及样品是采用Keithley SMU235,PR650评价发光效率和发光寿命,结果列于表2中:
表2本发明实施例制备的发光器件的发光特性
以上可以看出,本发明的双极磷光化合物作为发光主体材料在电致发光器件中进行应用,发光效率最高可达19.7cd/A,发光寿命为210hrs,较大的提高了器件的发光效率,是性能良好的有机发光材料。
虽然本发明用示范性实施方案进行了特别的描述,但应该理解在不偏离权利要求所限定的本发明的精神与范围的情况下,本领域普通技术人员可对其进行各种形式和细节上的改变。
Claims (5)
1.一种基于双极磷光衍生物的有机发光材料,其结构通式如式A所示:
其中,R1~R4独立的选自氢、C1-C4的烷基、取代或未取代的C6-C50芳基、取代或未取代的C7-C50芳烷基、取代或未取代的C6-C50芳胺、取代或未取代的C6-C50芳基膦、取代或未取代的C3-C50杂芳基中的任意一种;
R5~R8独立的选自氢、取代或未取代的C6-C50芳基、取代或未取代的C7-C50芳烷基、取代或未取代的C3-C50杂芳基中的任意一种。
2.根据权利要求1所述的基于双极磷光衍生物的有机发光材料,其特征在于,所述的R1~R4独立的选自氢、C1-C4的烷基、取代或未取代的C6-C30芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C6-C30芳胺、取代或未取代的C6-C30芳基膦、取代或未取代的C3-C30杂芳基中的任意一种;
R5~R8独立的选自氢、取代或未取代的C6-C30芳基、取代或未取代的C7-C30芳烷基、取代或未取代的C3-C30杂芳基中的任意一种。
3.根据权利要求1所述的基于双极磷光衍生物的有机发光材料,其特征在于,选自如下结构中的任意一种:
4.一种基于双极磷光衍生物的有机发光器件,包括第一电极、第二电极和置于所述两电极之间的一个或多个有机化合物层,其特征在于,至少一个有机化合物层包含至少一种如权利要求1~3任意一项中所述的基于双极磷光衍生物的有机发光材料。
5.根据权利要求4所述的一种基于双极磷光衍生物的有机发光器件,其特征在于,所述有机化合物层包括空穴注入层、空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。
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