CN113563315B - 化合物与有机电致发光器件、显示装置 - Google Patents
化合物与有机电致发光器件、显示装置 Download PDFInfo
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- CN113563315B CN113563315B CN202110807129.3A CN202110807129A CN113563315B CN 113563315 B CN113563315 B CN 113563315B CN 202110807129 A CN202110807129 A CN 202110807129A CN 113563315 B CN113563315 B CN 113563315B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 94
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 8
- -1 spirofluorene Chemical compound 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000003545 alkoxy 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
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical class C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 4
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- 229910052799 carbon Inorganic materials 0.000 claims description 2
- SNWQUNCRDLUDEX-UHFFFAOYSA-N inden-1-one Chemical compound C1=CC=C2C(=O)C=CC2=C1 SNWQUNCRDLUDEX-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 23
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- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
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- 238000000034 method Methods 0.000 description 7
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 4
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- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 3
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 3
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- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical group C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 2
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- 238000011056 performance test Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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Abstract
本申请涉及电致发光领域,公开一种化合物与有机电致发光器件、显示装置。该化合物的结构式如式(Ⅰ)所示:
Description
技术领域
本申请涉及电致发光领域,特别涉及一种化合物与有机电致发光器件、显示装置。
背景技术
当前,有机电致发光(OLED)显示技术已经在智能手机,平板电脑等领域获得应用,进一步还将向电视等大尺寸应用领域扩展。在近30年的发展过程中,人们研制出了各种性能优良的OLED材料,并通过对器件结构的不同设计,和对器件寿命、效率等性能的优化,加快了OLED的商业化进程,使得OLED在显示和照明领域得到了广泛应用。
空穴层、发光层以及其他有机功能层材料的选择也对器件的电流效率、驱动电压以及寿命产生较大的影响,目前仍在探索具有更高性能的功能层材料。
因此,为了满足人们对于OLED器件的更高要求,本领域亟待开发更多种类、更高性能的OLED材料。
发明内容
本申请公开了一种化合物与有机电致发光器件、显示装置,本申请化合物可以用做OLED发光器件的主体材料和电子传输材料,所得到的有机电致发光器件具有较低的驱动电压和较高的电流效率,尤其可适用于红光发光器件或绿光发光器件中,用于降低红光发光器件或绿光发光器件的驱动电压,提高两种器件的发光效率。
为达到上述目的,本申请提供以下技术方案:
本申请提供一种化合物,该化合物具有如式(Ⅰ)所示结构,
其中,X选自O或S;
R11、R21分别独立地选自氘、F、CN、含有1~20个碳原子的烷基、含有1~20个碳原子的烷氧基、含有6~40个碳原子的芳香基;
Ar、Ar1、Ar2分别独立地选自含有6~40个碳原子的芳香基;
Ar3选自含有6~40个碳原子的芳香基、或C-1~C-7中的一种,
其中X1~X12各自独立地选自NR1、O、S、CR2R3,并且X1和X2至少一个选自NR1,X3和X4至少一个选自NR1,X5和X6至少一个选自NR1,X7和X8至少一个选自NR1,X9和X10至少一个选自NR1,X11和X12至少一个选自NR1;R1选自含有1~20个碳原子的烷基或含有6~40个碳原子的芳香基;R2、R3各自独立地选自含有1~20个碳原子的烷基,含有6~40个碳原子的芳香基,并且R2和R3上的碳原子可以链接成环;C-1~C-7通过其SP2杂化的碳原子参与连接;
Z1、Z2、Z3分别独立地选自N或CR,其中,R选自氢、氘、含有1~20个碳原子的烷基、含有1~20个碳原子的烷氧基、含有6~40个碳原子的芳香基,并且,Z1、Z2、Z3至少一个选自N;
p选自0、1;
m、n选自0,1,2,3,4;
式(I)所示化合物中的氢可以被含有1~6个碳原子的烷基、含有1~6个碳原子的烷氧基、苯、联苯、萘、菲、蒽、芴、苯并芴、二苯并芴、三亚苯、荧蒽、芘、苝、螺芴、茚并芴或氢化的苯并蒽取代。
进一步地,Ar、Ar1、Ar2独立地选自苯、联苯、萘、菲、蒽、芴、苯并芴、二苯并芴、三亚苯、荧蒽、芘、苝、螺芴、茚并芴或氢化的苯并蒽中的一种或者两个以上基团的组合。
进一步地,R11、R21分别独立地选自氢、氘、F、CN、含有1~6个碳原子的烷基、含有1~6个碳原子的烷氧基、苯、联苯、萘、菲、蒽、芴、苯并芴、二苯并芴、三亚苯、荧蒽、芘、苝、螺芴、茚并芴或氢化的苯并蒽中的一种。
进一步地,Z1、Z2和Z3中至少两个选自N。
进一步地,Z1、Z2和Z3均选自N。
进一步地,Ar1、Ar2其中一个选自苯或联苯。
进一步地,Ar选自苯,p选自1。
进一步地,在所述式(1)中,X选自O或者S,Ar3选自苯、联苯或以下结构中的一个:
进一步地,所述化合物选自以下表1~表8中的化合物:
表1
表2
表3
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表4
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表5
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表6
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表7
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表8
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其中,表1~表8中所列化合物中,X选自O或者S,Ar3选自苯、联苯或者以下结构:
进一步地,式(Ⅰ)所示结构还包括以下结构化合物:
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本申请还提供一种有机电致发光器件,所述有机电致发光器件包括本申请化合物。
进一步地,所述有机电致发光器件的电子传输层的材料为本申请的化合物。
进一步地,所述有机电致发光器件的发光层主体材料为本申请的化合物。
进一步地,所述有机电致发光器件为红色器件。
进一步地,所述有机电致发光器件为红色磷光器件。
本申请还提供一种显示装置,该显示装置包括本申请提供的有机电致发光器件。
采用本申请的技术方案,产生的有益效果如下:
本申请提供了一种式(I)所示化合物,以螺芴氧杂蒽或螺芴硫杂蒽为母核,限定了各取代基在母环的取代位置,同时限定了特定的取代基团,用于改善材料性能,以使利用本申请化合物所制备的有机电致发光器件具有较高的发光效率、较低的驱动电压和较长的寿命。
具体实施方式
下面将结合本申请实施例,对本申请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申请一部分实施例,而不是全部的实施例。基于本申请中的实施例,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,都属于本申请保护的范围。
需要说明的是:本申请中,如果没有特别的说明,本文所提到的所有实施方式以及优选实施方法可以相互组合形成新的技术方案。本申请中,如果没有特别的说明,本文所提到的所有技术特征以及优选特征可以相互组合形成新的技术方案。本申请中,如果没有特别的说明,百分数(%)或者份指的是相对于组合物的重量百分数或重量份。本申请中,如果没有特别的说明,所涉及的各组分或其优选组分可以相互组合形成新的技术方案。本申请中,除非有其他说明,数值范围“a~b”表示a到b之间的任意实数组合的缩略表示,其中a和b都是实数。例如数值范围“6~22”表示本文中已经全部列出了“6~22”之间的全部实数,“6~22”只是这些数值组合的缩略表示。本申请所公开的“范围”以下限和上限的形式,可以分别为一个或多个下限,和一个或多个上限。本申请中,除非另有说明,各个反应或操作步骤可以顺序进行,也可以不按照顺序进行。优选地,本文中的反应方法是顺序进行的。
除非另有说明,本文中所用的专业与科学术语与本领域熟练人员所熟悉的意义相同。此外,任何与所记载内容相似或均等的方法或材料也可应用于本申请中。
中间体的合成:
(1)中间体M-1的合成:
500毫升三口瓶,氮气保护,加入5.5克M-0所示化合物,200毫升干燥的四氢呋喃,降温至-78℃,并控制-70-78℃以下,滴加6.25毫升1.6M的丁基锂的正己烷溶液,加毕,控制-70~78℃保持1小时,一次性加入2.54克碘,然后缓慢升温至20℃,并在20~25℃保持2小时,加水、二氯甲烷分液,二氯甲烷层水洗,1%亚硫酸氢钠溶液洗涤,浓缩至干后,用氯苯和乙醇混合溶剂结晶3次,得到M-1所示化合物3.8克。
对M-1所示化合物进行了质谱检测,最大的两个峰为538,536,确定M-1分子式为C25H14BrIO。
合成实施例1-化合物1的合成:
(1)M-2的合成
250毫升三口瓶,氮气保护,加入80毫升二氧六环,20毫升水,再加入5.37克(0.01mol)M1-1所示化合物,1.22克(0.01mol)苯硼酸,2.12克(0.02mol)碳酸钠,0.115克(0.0001mol)四三苯基膦钯,缓慢升温至60℃反应6小时,降温,加水和甲苯分液,有机层水洗后,硫酸镁干燥,过滤除去硫酸镁后,减压除去溶剂,得到的固体用乙醇和氯苯混合溶剂重结晶,得到式M-2所示化合物3.9克。
对式M-2所示化合物进行了质谱检测,最大的两个峰为486,488,确定M-2分子式为C31H19BrO。
(2)M-3的合成
500毫升三口瓶,氮气保护,加入4.87克M-2所示化合物,300毫升干燥的四氢呋喃,降温至-78℃,并控制-70-78℃以下,滴加8毫升1.6M的丁基锂的正己烷溶液,加毕,控制-70-78℃保持1小时,一次性加入1.8克硼酸三甲酯,然后缓慢升温至20℃,并在20~25℃保持4小时,加水、乙酸乙酯分液,有机层水洗,浓缩至干后,得到M-3所示化合物,未经进一步提纯,直接进行下步反应。
(3)化合物1的合成
500毫升三口瓶,氮气保护,加入300毫升二氧六环,60毫升水,再加入上步得到的未经提纯的M-3所示化合物,3.88克2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪,2.12克碳酸钠,0.115克四三苯基膦钯,缓慢升温至回流反应8小时,降温,加水和甲苯分液,有机层水洗后,硫酸镁干燥,过滤除去硫酸镁后,减压除去溶剂,得到的固体用热丙酮煮沸洗涤,得到式1所示化合物6.1克。
对式1所示化合物进行了质谱检测,m/z为715。
合成实施例2-化合物2的合成:
参照化合物1的合成,只是在第(3)步中,将其中的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪换成2-([1,1'-联苯]-4-基)-4-(4-溴苯基)-6-苯基-1,3,5-三嗪,得到式2所示化合物。
对式2所示化合物进行了质谱检测,m/z为791。
合成实施例3-化合物3的合成:
参照化合物1的合成,只是在第(3)步中,将其中的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪换成2-(4-溴苯基)-4-(9,9-二甲基-9H-芴-2-基)-6-苯基-1,3,5-三嗪,得到式3所示化合物。
对式3所示化合物进行了质谱检测,m/z为831。
合成实施例4-化合物4的合成:
参照化合物1的合成,只是在第(3)步中,将其中的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪换成2,4-二([1,1'-联苯]-4-基)-6-(4-溴苯基)-1,3,5-三嗪,得到式4所示化合物。
对式4所示化合物进行了质谱检测,m/z为867。
合成实施例5-化合物5-8的合成:
分别参照化合物1-4的合成,只是在第(1)步中,将其中的苯硼酸换成3-苯基苯硼酸,得到化合物5-8。
对式5所示化合物进行了质谱检测,m/z为791。
对式6所示化合物进行了质谱检测,m/z为867。
对式7所示化合物进行了质谱检测,m/z为907。
对式8所示化合物进行了质谱检测,m/z为943。
合成实施例6化合物9-12的合成:
分别参照化合物1-4的合成,只是在第(1)步中,将其中的苯硼酸换成N-苯基咔唑-3-硼酸,得到化合物9-12。
对式9所示化合物进行了质谱检测,m/z为880。
对式10所示化合物进行了质谱检测,m/z为956。
对式11所示化合物进行了质谱检测,m/z为996。
对式12所示化合物进行了质谱检测,m/z为1032。
合成实施例7-化合物13~16的合成:
参照化合物1的合成,只是在第(3)步中,将其中的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪换成2-溴-4,6-二苯基-1,3,5-三嗪,得到式13所示化合物。
对式13所示化合物进行了质谱检测,m/z为639。
参照化合物1的合成,只是在第(3)步中,将其中的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪换成2-溴-4-苯基-6-(4-联苯基)-1,3,5-三嗪得到式14所示化合物。
对式14所示化合物进行了质谱检测,m/z为715。
参照化合物1的合成,只是在第(3)步中,将其中的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪换成2-溴-4-2-萘基-6-苯基-1,3,5-三嗪,得到式15所示化合物。
对式15所示化合物进行了质谱检测,m/z为689。
参照化合物1的合成,只是在第(3)步中,将其中的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪换成2,4-二([1,1'联苯]-4-基)-6-溴-1,3,5-三嗪,得到式16所示化合物。
对式16所示化合物进行了质谱检测,m/z为791。
合成实施例8-化合物21的合成:
参照化合物13的合成,只是在第(1)步中,将其中的苯硼酸换成N-苯基咔唑-3-硼酸,得到式21所示化合物。
对式21所示化合物进行了质谱检测,m/z为804。
合成实施例9-化合物25的合成:
参照化合物13的合成,只是在第(1)步中,将其中的苯硼酸换成4-(N-咔唑基)苯硼酸,得到式25所示化合物。
对式25所示化合物进行了质谱检测,m/z为804。
合成实施例10-化合物P-1的合成:
(1)(7,7-二甲基-5-苯基-5,7-二氢吲哚并[2,1-b]咔唑-9-基)硼酸的合成
参照M-3的合成,使相应的溴代物依次和丁基锂、硼酸三甲酯反应,水解后制备得到(7,7-二甲基-5-苯基-5,7-二氢吲哚并[2,1-b]咔唑-9-基)硼酸。
(2)化合物P-1的合成
参照化合物1的合成,只是将其中的苯硼酸换为上步制备得到的(7,7-二甲基-5-苯基-5,7-二氢吲哚并[2,1-b]咔唑-9-基)硼酸,得到化合物P-1。
对P-1所示化合物进行了质谱检测,m/z为996。
合成实施例11化合物P-10的合成:
(1)(12,12-二甲基-11-苯基-11,12-二氢吲哚并[2,1-a]咔唑-8-基)硼酸的合成
参照M-3的合成,使相应的溴代物依次和丁基锂、硼酸三甲酯反应,水解后制备得到(12,12-二甲基-11-苯基-11,12-二氢吲哚并[2,1-a]咔唑-8-基)硼酸。
(2)化合物P-10的合成
参照化合物1的合成,只是将其中的苯硼酸换为上步制备得到的(12,12-二甲基-11-苯基-11,12-二氢吲哚并[2,1-a]咔唑-8-基)硼酸,得到化合物P-10。
对P-10所示化合物进行了质谱检测,m/z为996。
合成实施例12化合物P-19的合成:
参照化合物P-1的合成,只是将其中的2-(4-溴苯基)-4,6-二苯基-1,3,5-三嗪换成2-溴-4,6-二苯基-1,3,5-三嗪,得到化合物P-19。
对P-19所示化合物进行了质谱检测,m/z为920。
其它未具体描述合成方法的化合物,可以采用本领域公知的方法,采用常规反应合成。
器件实施例中所用的材料:
器件实施例1
实施例选用本申请的化合物作为有机电致发光器件中的电子传输材料,比较例选用H-1、H-3、H-6作为有机电致发光器件中的电子传输材料。
有机电致发光器件结构为:ITO/HIL02(100nm)/NPB(40nm)/EM1(30nm)/电子传输材料(30nm)/LiF(0.5nm)/Al(150nm)。
有机电致发光器件制备过程如下:
将涂布了ITO透明导电层(作为阳极)的玻璃基板在清洗剂中进行超声处理,然后在去离子水中冲洗,再在丙酮与乙醇混合溶剂中超声除油,再在洁净环境下烘烤至完全除水,用紫外光和臭氧清洗,并用低能阳离子束轰击表面,以改善表面的性质,提高与空穴注入层的结合能力;
将上述玻璃基板置于真空腔内,抽真空至1×10-5~9×10-3Pa,在阳极上真空蒸镀HIL02作为空穴注入层,蒸镀速率0.1nm/s,蒸镀膜厚为100nm;
在空穴注入层上真空蒸镀NPB作为空穴传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为40nm;
在空穴传输层之上真空蒸镀EM1作为器件的有机发光层,蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm;
在有机发光层之上分别真空蒸镀对比化合物和本发明化合物作为有机电致发光器件的电子传输层;其蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm;
在电子传输层上真空蒸镀0.5nm的LiF、150nm的Al作为电子注入层和阴极。
测量了所制备有机电致发光器件的亮度、驱动电压、电流效率。
有机电致发光器件性能见下表9。使用杭州远方生产的OLED-1000多通道加速老化寿命与光色性能分析***测试。
表9
电子传输材料 | 要求亮度cd/m2 | 驱动电压V | 电流效率cd/A |
HT-1 | 1000 | 5.08 | 1.62 |
HT-3 | 1000 | 4.88 | 1.05 |
HT-6 | 1000 | 5.01 | 1.77 |
化合物1 | 1000 | 4.56 | 1.90 |
化合物2 | 1000 | 4.61 | 2.01 |
化合物4 | 1000 | 4.49 | 1.96 |
化合物15 | 1000 | 4.55 | 1.89 |
化合物30 | 1000 | 4.60 | 1.99 |
化合物37 | 1000 | 3.88 | 2.01 |
化合物40 | 1000 | 4.71 | 2.24 |
化合物41 | 1000 | 4.69 | 2.33 |
化合物42 | 1000 | 4.86 | 2.19 |
从表9中的数据可以看出,与对比例相比,利用本申请实施例的化合物制备得到的有机电致发光器件,驱动电压有明显降低,电流效率明显提升,化合物37电压降低更为明显,化合物40~42在效率提升方面效果更好。
器件实施例2
实施例选用本申请的化合物作为有机电致发光器件中的红光主体材料,比较实施例选用H-2、H-4、H-5作为有机电致发光器件中的红光主体材料。
有机电致发光器件的结构为:ITO/NPB(40nm)/红光主体材料(35nm):Ir(piq)3[10%]/TPBI(10nm)/Alq3(15nm)/LiF(0.5nm)/Al(150nm)。其中“Ir(piq)3[10%]”是指红光染料的掺杂比例,即红光主体材料与Ir(piq)3的重量份比为100:10。
有机电致发光器件制备过程如下: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空穴传输层NPB,蒸镀速率为0.1nm/s,蒸镀膜厚为40nm;
在空穴传输层之上真空蒸镀红光主体材料和染料Ir(piq)3,作为有机电致发光器件的发光层,蒸镀速率为0.1nm/s,蒸镀总膜厚为35nm;;
在发光层之上依次真空蒸镀电子传输层TPBI和Alq3,其蒸镀速率均为0.1nm/s,蒸镀膜厚分别为10nm和15nm;
在电子传输层上真空蒸镀0.5nm的LiF,150nm的Al作为电子注入层和阴极。
所有有机电致发光器件均采用上述方法制备得到,区别仅在于红光主体材料的选择,具体详见下表10。
性能测试:
使用杭州远方生产的OLED-1000多通道加速老化寿命与光色性能分析***测试测量了所制备有机电致发光器件的亮度、驱动电压、电流效率,测试结果如下表所示。
表10
由上表可知,相较于对比化合物,本申请提供的化合物作为有机电致发光器件的红光主体材料,能够提高发光效率,降低驱动电压,对应化合物P-40~P-43,虽然效率没有提升,但是电压降低明显。
显然,本领域的技术人员可以对本申请实施例进行各种改动和变型而不脱离本申请的精神和范围。这样,倘若本申请的这些修改和变型属于本申请权利要求及其等同技术的范围之内,则本申请也意图包含这些改动和变型在内。
Claims (8)
1.一种化合物,其特征在于,所述化合物具有式(Ⅰ)所示结构:
其中,X选自O或S;
R11、R21分别独立地选自氘、CN、含有1~20个碳原子的烷基、含有1~20个碳原子的烷氧基、苯;
Ar、Ar1、Ar2独立地选自苯、联苯、萘、菲、蒽、芴、苯并芴、二苯并芴、三亚苯、荧蒽、芘、苝、螺芴、茚并芴或氢化的苯并蒽中的一种或者两个的组合;
Ar3选自苯、联苯或C-1~C-7中的一种,
其中X1~X12各自独立地选自NR1、O、S、CR2R3,并且X1和X2至少一个选自NR1,X3和X4至少一个选自NR1,X5和X6至少一个选自NR1,X7和X8至少一个选自NR1,X9和X10至少一个选自NR1,X11和X12至少一个选自NR1;R1选自含有1~20个碳原子的烷基或含有6~40个碳原子的芳香基;R2、R3各自独立地选自含有1~20个碳原子的烷基,含有6~40个碳原子的芳香基,并且R2和R3上的碳原子可以链接成环;C-1~C-7通过其SP2杂化的碳原子参与连接;
Z1、Z2、Z3分别独立地选自N或CR,其中,R选自氢、氘,并且,Z1、Z2、Z3至少一个选自N;
p选自0、1;
m、n选自0,1;
式(I)所示化合物中的氢可以被苯、含有1~6个碳原子的烷基取代。
2.根据权利要求1所述的化合物,其特征在于,Z1、Z2和Z3中至少两个选自N。
3.根据权利要求1所述的化合物,其特征在于,Z1、Z2和Z3均选自N。
4.根据权利要求1所述的化合物,其特征在于,Ar1、Ar2其中一个选自苯或联苯。
5.根据权利要求1所述的化合物,其特征在于,Ar选自苯,p选自1。
6.根据权利要求1所述的化合物,其特征在于,在所述式(1)中,X选自O或者S,Ar3选自苯、联苯或以下结构中的一个:
7.一种有机电致发光器件,其特征在于,所述有机电致发光器件包括如权利要求1-6任一项所述的化合物。
8.一种显示装置,其特征在于,包括如权利要求7所述的有机电致发光器件。
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