CN116514752B - 一种发光辅助材料及制备方法与其在有机电致发光器件中的应用 - Google Patents
一种发光辅助材料及制备方法与其在有机电致发光器件中的应用 Download PDFInfo
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 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 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 238000001126 phototherapy Methods 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明属于有机发光材料技术领域,涉及一种有机化合物及其制备方法和有机电致发光器件,具体涉及一种发光辅助材料及制备方法与其在有机电致发光器件中的应用。本发明公开的发光辅助材料具有如说明书所述化学式I所示结构。本发明的母核中2个9‑甲基‑9‑苯基‑芴调节平衡化合物的分子量,进而调控蒸镀温度,化合物更稳定,避免了因为材料蒸镀温度的上升而带来的长时间蒸镀劣化风险,从而降低驱动,进而提高器件寿命。
Description
技术领域
本发明属于有机发光材料技术领域,涉及一种发光辅助材料及其制备方法与其在制备有机电致发光器件中的应用。
背景技术
通常,有机发光现象是指利用有机物质将电能转换为光能的现象。利用有机发光现象的有机电气元件通常具有阳极、阴极及它们之间包括有机物层的结构。在此,有机物层为了提高有机电气元件的效率和稳定性而普遍形成为由各种不同物质构成的多层结构,例如,可以由空穴注入层、空穴输送层、发光层、电子输送层及电子注入层等形成。
利用该有机EL器件,从两个电极注入的电荷在发光层中重新组合以获得发光。在这种情况下,如何有效地将空穴和电子的电荷转移到发光层是重要的,并且该器件需要具有优异的载流子平衡。而且,通过增强阻挡从阴极注入的电子的空穴注入特性和电子阻挡特性以增加空穴和电子的复合概率,以及通过限制在发光层内产生的激子,发光效率得以提高。因此,发光辅助材料的作用是如此重要。
有机电致发光材料的研究已经在学术界和工业界广泛开展,但目前为止还未充分开发出稳定又高效的有机电气元件用的有机物层材料,而且该技术的产业化进程仍面临许多关键问题,所以,开发新的材料,一直是本领域技术人员亟待解决的问题。
发明内容
有鉴于此,本发明提供了一种发光辅助材料及其制备方法和在有机电致发光器件中的应用。
为了实现上述目的,本发明的第一个目的在于提供一种发光辅助材料。
采用如下技术方案:
所述发光辅助材料的结构通式为化学式I:
;
化学式I
化学式I中:
R1、R2、R3、R4可以相同也可以不同,分别独立表示氢、氘、取代或未经取代的C1-C8烷基、取代或未经取代的C6-C30芳基,且R1、R2、R3、R4相邻的取代基之间不可成环;
R5、R6可以相同也可以不同,独立表示氢、取代或未经取代的C1-C5烷基、取代或未经取代的C6-C12芳基;
Ar独立表示以下基团:
;其中,
R11~R25可以相同也可以不同,独立表示氢、取代或未经取代的C1-C5烷基、取代或未经取代的C6-C18芳基;
R26独立表示取代或未取代的C6-C15芳基;
R27独立表示取代或未取代的C6-C15亚芳基;
进一步地,R1、R2、R3、R4分别独立表示氢;
R5、R6分别独立表示氢、甲基、苯基;
R11~R25可以相同也可以不同,独立表示氢、苯基;
R26独立表示苯基、联苯基;
R27独立表示亚苯基、亚联苯基;
进一步地,上述化学式I的结构通式为:
。
其中上述化学式-I-1~化学式-I-9中R1-R4、Ar如上述所定义。
本发明中,“取代”意指被选自以下的一个、两个或更多个取代基取代:氢、氘、三氟甲基、甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基丁基、1-乙基丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、1-甲基己基、苯基、萘基、蒽基、菲基、噻吩基、呋喃基、吡咯基、苯并噻吩基、苯并呋喃基、环戊烷基、环己烷基。
在上述技术方案中,进一步优选所述发光辅助材料为下述结构中的任意一个,但不限于此:
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本发明的发光辅助材料可通过所属领域的技术人员已知的合成方法制备。举例来说,优选以下反应流程来制备。
合成路线1:
;
上述式中,R1-R6、Ar如上述化学式Ⅰ中所定义,Hal1-Hal2各自独立的选自氯、溴或碘。
说明:相对于没有公开复杂的原料,将采用经典的Suzuki偶联反应和/或Buchwald–Hartwig偶联反应合成,并应用到本发明中。
步骤1、中间体1的制备
将原料A(1.0eq)溶于甲苯中,原料B(1.2eq)溶于甲苯中,随后将原料B溶液缓慢滴加到原料A溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至80℃-120℃,并回流反应4-12h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(V二氯甲烷:V石油醚=1:10)的混合溶液,通过柱色谱法纯化,除去杂质,从而获得中间体1;
步骤2、化学式I的制备
将中间体1(1.0eq)溶于甲苯中,原料C(1.0eq)溶于甲苯中,随后将原料C溶液缓慢滴加到中间体1溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至80℃-120℃,并回流反应4-12h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(V二氯甲烷:V石油醚=1:6)的混合溶液,通过柱色谱法纯化剩余物质获得化学式I。
与现有技术相比,本发明提供的发光辅助材料,引入三芳胺基团,避免载流子迁移局域化,能够降低空穴传输能障,从而提升迁移速率,提升发光效率。因为芴结构中心碳原子为SP3杂化,不参与共轭,因此芴结构中除去与N相连的苯基之外的基团对材料电子性能影响较弱。母核中2个9-甲基-9-苯基-芴调节平衡化合物的分子量,进而调控蒸镀温度,化合物更稳定,避免了因为材料蒸镀温度的上升而带来的长时间蒸镀劣化风险,从而降低驱动,进而提高器件寿命。
附图说明
图1为化合物-3的核磁共振氢谱图。
具体实施方式
需要说明的是,基于上述合成路线而言,下述实施例1-实施例2中原料A和原料C不仅为同一物质,而且为现有技术,CAS号为:2249965-87-3。
实施例1
实施例1中所涉及原料B的CAS号为:4106-66-5;
;
将原料A-3(1.0eq)溶于甲苯中,原料B-3(1.2eq)溶于甲苯中,随后将原料B-3溶液缓慢滴加到原料A-3溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至100℃,并回流反应10h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(V二氯甲烷:V石油醚=1:10)的混合溶液,通过柱色谱法纯化,除去杂质,从而获得中间体1(产率:88.7%);
将中间体1(1.0eq)溶于甲苯中,原料A-3(1.0eq)溶于甲苯中,随后将原料A-3溶液缓慢滴加到中间体1溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至100℃,并回流反应10h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(V二氯甲烷:V石油醚=1:6)的混合溶液,通过柱色谱法纯化剩余物质获得化合物-3(产率:78.6%)。
对所得化合物-3进行检测分析,结果如下:
HPLC纯度:>99%。
质谱测试(质谱采用超高液相质谱联用仪,ESI源进行测试,下同):测试值为691.98。
元素分析:
计算值为:C, 90.27; H, 5.39; N, 2.02; O, 2.31。
测试值为:C, 90.02; H, 5.52; N, 2.25; O, 2.54。
核磁共振氢谱图:如图1所示。
实施例2
实施例2中所涉及原料B的CAS号为:578027-21-1;
;
将原料A-10(1.0eq)溶于甲苯中,原料B-10(1.2eq)溶于甲苯中,随后将原料B-10溶液缓慢滴加到原料A-10溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至120℃,并回流反应12h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(V二氯甲烷:V石油醚=1:10)的混合溶液,通过柱色谱法纯化,除去杂质,从而获得中间体1(产率:83.4%);
将中间体1(1.0eq)溶于甲苯中,原料A-10(1.0eq)溶于甲苯中,随后将原料A-10溶液缓慢滴加到中间体1溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至100℃,并回流反应10h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(V二氯甲烷:V石油醚=1:6)的混合溶液,通过柱色谱法纯化剩余物质获得化合物-10(产率:79.4%)。
对所得化合物-10进行检测分析,结果如下:
HPLC纯度:>99%。
质谱测试(质谱采用超高液相质谱联用仪,ESI源进行测试,下同):测试值为768.11。
元素分析:
计算值为:C, 90.71; H, 5.38; N, 1.82; O, 2.08。
测试值为:C, 90.48; H, 5.61; N, 1.97; O, 2.18。
实施例3
实施例3中所涉及原料A和原料B,均为现有技术,其中,原料A的CAS号为:2128245-45-2;原料B的CAS号为:2102493-87-6;
;
将原料A-323(1.0eq)溶于甲苯中,原料B-323(1.2eq)溶于甲苯中,随后将原料B-323溶液缓慢滴加到原料A-323溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至120℃,并回流反应12h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(V二氯甲烷:V石油醚=1:10)的混合溶液,通过柱色谱法纯化,除去杂质,从而获得中间体1(产率:85.0%);
将中间体1(1.0eq)溶于甲苯中,原料C-323(1.0eq)溶于甲苯中,随后将原料C-323溶液缓慢滴加到中间体1溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至100℃,并回流反应10h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(V二氯甲烷:V石油醚=1:6)的混合溶液,通过柱色谱法纯化剩余物质获得化合物-323(产率:78.1%)。
对所得化合物-323进行检测分析,结果如下:
HPLC纯度:>99%。
质谱测试(质谱采用超高液相质谱联用仪,ESI源进行测试,下同):测试值为780.18。
元素分析:
计算值为:C, 92.39; H, 5.82; N, 1.80。
测试值为:C, 92.04; H, 6.06; N, 2.11。
因结构通式为发明内容中的化学式I,其他化合物的合成路线和原理均与上述所列举的实施例相同。其中,本发明实施例4~91按照上述制备方法可得到如下表1所示的发光辅助材料。
表1
实施例 | 化合物 | 质谱测试值 |
实施例4 | 1 | 691.99 |
实施例5 | 2 | 691.97 |
实施例6 | 5 | 692.01 |
实施例7 | 6 | 692.03 |
实施例8 | 11 | 768.10 |
实施例9 | 12 | 768.07 |
实施例10 | 13 | 768.12 |
实施例11 | 17 | 768.09 |
实施例12 | 19 | 768.15 |
实施例13 | 37 | 768.11 |
实施例14 | 38 | 768.14 |
实施例15 | 39 | 768.16 |
实施例16 | 40 | 768.20 |
实施例17 | 41 | 768.13 |
实施例18 | 42 | 768.16 |
实施例19 | 43 | 768.10 |
实施例20 | 45 | 768.14 |
实施例21 | 46 | 768.09 |
实施例22 | 48 | 768.08 |
实施例23 | 49 | 768.15 |
实施例24 | 52 | 768.08 |
实施例25 | 59 | 768.11 |
实施例26 | 60 | 768.07 |
实施例27 | 64 | 768.11 |
实施例28 | 65 | 768.12 |
实施例29 | 66 | 768.16 |
实施例30 | 71 | 768.09 |
实施例31 | 72 | 768.13 |
实施例32 | 73 | 706.08 |
实施例33 | 75 | 782.21 |
实施例34 | 77 | 706.05 |
实施例35 | 85 | 844.21 |
实施例36 | 94 | 782.16 |
实施例37 | 100 | 782.13 |
实施例38 | 103 | 782.15 |
实施例39 | 115 | 796.17 |
实施例40 | 124 | 708.06 |
实施例41 | 125 | 708.10 |
实施例42 | 126 | 708.14 |
实施例43 | 127 | 708.03 |
实施例44 | 129 | 708.11 |
实施例45 | 132 | 708.20 |
实施例46 | 133 | 784.15 |
实施例47 | 137 | 784.18 |
实施例48 | 138 | 784.13 |
实施例49 | 139 | 784.16 |
实施例50 | 140 | 784.20 |
实施例51 | 142 | 784.16 |
实施例52 | 151 | 784.10 |
实施例53 | 152 | 784.16 |
实施例54 | 153 | 784.15 |
实施例55 | 160 | 784.14 |
实施例56 | 161 | 784.18 |
实施例57 | 162 | 784.20 |
实施例58 | 165 | 784.16 |
实施例59 | 172 | 784.13 |
实施例60 | 174 | 784.22 |
实施例61 | 208 | 860.25 |
实施例62 | 231 | 860.23 |
实施例63 | 251 | 718.06 |
实施例64 | 252 | 718.09 |
实施例65 | 254 | 718.14 |
实施例66 | 255 | 718.17 |
实施例67 | 259 | 794.16 |
实施例68 | 260 | 794.18 |
实施例69 | 261 | 794.16 |
实施例70 | 270 | 794.20 |
实施例71 | 287 | 794.18 |
实施例72 | 288 | 794.16 |
实施例73 | 290 | 794.25 |
实施例74 | 291 | 794.22 |
实施例75 | 292 | 794.18 |
实施例76 | 293 | 794.20 |
实施例77 | 294 | 794.21 |
实施例78 | 305 | 794.15 |
实施例79 | 306 | 794.18 |
实施例80 | 317 | 794.20 |
实施例81 | 322 | 780.16 |
实施例82 | 328 | 780.17 |
实施例83 | 329 | 780.15 |
实施例84 | 345 | 870.31 |
实施例85 | 386 | 767.10 |
实施例86 | 387 | 767.14 |
实施例87 | 394 | 767.18 |
实施例88 | 396 | 767.20 |
实施例89 | 405 | 843.21 |
实施例90 | 425 | 843.25 |
实施例91 | 426 | 843.19 |
采用上述实施例提供的发光辅助材料制备得到的有机电致发光器件,当有机物层为发光辅助层时,所述发光辅助层包括上述实施例提供的发光辅助材料。
本发明的有机发光器件的有机材料层可以形成为单层结构,但也可以形成为其中层和有两个或更多个有机材料层的多层结构。例如,本发明的有机发光器件可以具有包括空穴注入层、空穴传输层、空穴注入和传输层、电子阻挡层、发光层、电子传输层、电子注入层、空穴阻挡层、电子注入和传输层等作为有机材料层的结构。然而,有机发光器件的结构不限于此,并且可以包括更少数量的有机材料层或更多数量的有机材料层。
作为阳极材料,通常优选具有大功函数的材料使得空穴顺利注入有机材料层。在本发明中能够使用的阳极材料的具体实例包括:金属,例如钒、铬、铜、锌和金,或其合金;金属氧化物,例如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(3-甲基噻吩)、聚[3 ,4-(乙烯-1 ,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺,但不限于此。
空穴注入材料是有利地在低电压下接收来自阳极的空穴的材料,并且空穴注入材料的最高占据分子轨道(HOMO)优选地在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖啶酮的有机材料、基于苝的有机材料、蒽醌、以及基于聚苯胺和基于聚噻吩的导电聚合物等,但不限于此,并且还可以包含能够进行p掺杂的另外化合物。
空穴传输材料是能够接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,并且具有高空穴迁移率的材料是合适的。其具体实例包括基于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等,但不限于此。
发光层可以发射红色、绿色或蓝色的光,并且可以由磷光材料或荧光材料形成。发光材料是能够通过接收分别来自空穴传输层和电子传输层的空穴和电子并使空穴与电子结合而发出在可见光区域内的光的材料,并且优选为对荧光或磷光具有有利的量子效率的材料。其具体实例包括:8-羟基喹啉铝配(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并咔唑、基于苯并噻唑和基于苯并咪唑的化合物;基于聚(对亚苯基亚乙烯基) (PPV)的聚合物;螺环化合物;聚芴;红荧烯等,但不限于此。
发光层的主体材料包括稠合芳族环衍生物、含杂环的化合物等。具体地,稠合芳族环衍生物包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,含杂环的化合物包括咔唑衍生物、二苯并呋喃衍生物、梯子型呋喃化合物、嘧啶衍生物等,然而,材料不限于此。
电子传输层可以起到促进电子传输的作用。电子传输材料是有利地接收来自阴极的电子并将电子传输至发光层的材料,具有高电子迁移率的材料是合适的。其具体实例包括:8-羟基喹啉的Al配合物;包含Alq3的配合物;有机自由基化合物;羟基黄酮-金属配合物;等等,但不限于此。电子传输层的厚度可以为1nm至50nm。厚度为1nm或更大的电子传输层具有防止电子传输特性下降的优点,并且厚度为50nm或更小具有防止由电子传输层太厚引起的用于增强电子迁移的驱动电压增加的优点。
电子注入层可以起到促进电子注入的作用。电子注入材料优选为这样的化合物:其具有传输电子的能力,具有来自阴极的注入电子效应,对发光层或发光材料具有优异的电子注入效应,防止发光层中产生的激子迁移至空穴注入层,并且除此之外,具有优异的薄膜形成能力。其具体实例包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等及其衍生物,金属配合物,含氮5元环衍生物等,但不限于此。
作为阴极材料,通常优选具有小功函数的材料使得电子顺利注入有机材料层。阴极材料的具体实例包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡、铅或其合金;多层结构材料,例如LiF/Al或LiO2/Al等等,但不限于此。
本申请所述的器件可以用于有机发光装置,包括但不限于平板显示器,计算机监视器,一种医用监护仪,一种电视机,广告牌,一种用于内部或外部照明和/或信号的灯,平视显示器,全透明或部分透明的显示器,柔性显示器,一种激光打印机,一种电话机,一种手机,片剂,一个相簿,个人数字助理(PDA),一种可穿戴装置,一种笔记本电脑,一种数码相机,摄像机,取景器,微型显示器,三维显示器,虚拟现实或增强现实显示器,车辆,包括平铺在一起的多个显示器的视频墙,剧场或场馆屏幕,光疗装置和标志。
器件实施例1: 红光有机电致发光器件制备
所制备OLED器件的结构为:ITO阳极/HIL/HTL/发光辅助层/EML/HBL/ETL /EIL/阴极/光取出层
a、ITO阳极:将涂层厚度为1500Å的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,用甲醇、丙酮、异丙醇依次超声波洗涤(每次洗涤5 min),干燥,然后转移至等离子体清洗机内洗涤5min,再送至蒸镀机中,以该基板为阳极,在其上依次蒸镀其它功能层。
b、HIL(空穴注入层):以1Å/s的蒸镀速率,真空蒸镀空穴注入层材料HT和P-dopant,其化学式如下所示;所述HT和P-dopant的蒸镀速率比为97:3,厚度为10nm;
c、HTL(空穴传输层):以1.5Å/s的蒸镀速率,在空穴注入层上面真空蒸镀130nm的HT作为空穴传输层;
d、发光辅助层:以0.5Å/s的蒸镀速率,在空穴传输层上面真空蒸镀10nm的上述实施例提供的化合物1作为发光辅助层;
e、EML(发光层):然后在上述发光辅助层上,以1Å/s的蒸镀速率,真空蒸镀厚度为20nm的主体材料(Host-1)和掺杂材料(Dopant)作为发光层,其Host-1和Dopant的化学式如下所示;其中双Host-1和Dopant的蒸镀速率比为98:2。
f、HBL(空穴阻挡层):以0.5Å/s的蒸镀速率,真空蒸镀厚度为5.0nm的空穴阻挡层HB。
g、ETL(电子传输层):以1Å/s的蒸镀速率,真空蒸镀厚度为35nm的ET和Liq作为电子传输层,其ET的化学式如下所示;其中ET和Liq的蒸镀速率比为50:50。
h、EIL(电子注入层):以0.5Å/s的蒸镀速率,蒸镀Yb膜层1.0nm,形成电子注入层。
i、阴极:以1Å/s的蒸镀速率比,蒸镀镁和银18nm,其蒸镀速率比为1:9,得到OLED器件。
j、光取出层:以1Å/s的蒸镀速率,在阴极上真空蒸镀厚度为70nm的CPL,作为光取出层。
K、随后将蒸镀完成的基板进行封装:首先采用涂胶设备将清洗后盖板用UV胶进行涂覆工艺,然后将涂覆完成的盖板移至压合工段,将蒸镀完成的基板置于盖板上端,最后将基板和盖板在贴合设备作用下进行贴合,同时完成对UV胶光照固化。
。
参照上述器件实施例1提供的方法,分别选用化合物2、3、6、10、17、37、38、39、40、43、46、52、64、65、66、73、85、94、100、125、126、129、132、133、142、161、162、208、251、252、254、255、259、260、261、290、305、317、322、323、386、394、396替代化合物1,进行发光辅助层的蒸镀,并制备得到相应的有机电致发光器件,分别记为器件实施例2~44。
器件对比例1-7:
该对比例提供了一种有机电致发光器件,该有机电致发光器件的制备方法与器件实施例1的唯一区别在于,该有机电致发光器件是采用现有的对比化合物a、b、c、d、e、f、g替代上述器件实施例1中的发光辅助材料(化合物1)进行蒸镀。其中,对比化合物a、b、c、d、e、f、g的化学结构式如下:
。
在6000(nits)亮度下对上述器件实施例1~44以及器件对比例1~7得到的有机电致发光器件的驱动电压、发光效率以及寿命进行表征,测试结果如下表2:
表2
有机电致发光器件 | 发光辅助材料 | 驱动电压(V) | 发光效率(cd/A) | CIEx | CIEy | T95寿命(h) |
对比例1 | 化合物a | 3.58 | 45.3 | 0.686 | 0.313 | 1466 |
对比例2 | 化合物b | 3.60 | 45.9 | 0.687 | 0.312 | 1471 |
对比例3 | 化合物c | 3.59 | 46.2 | 0.685 | 0.314 | 1473 |
对比例4 | 化合物d | 3.64 | 47.3 | 0.685 | 0.314 | 1462 |
对比例5 | 化合物e | 3.57 | 48.0 | 0.686 | 0.313 | 1477 |
对比例6 | 化合物f | 3.61 | 47.6 | 0.684 | 0.315 | 1469 |
对比例7 | 化合物g | 3.63 | 47.0 | 0.687 | 0.312 | 1465 |
器件实施例1 | 1 | 3.46 | 55.0 | 0.686 | 0.313 | 1533 |
器件实施例2 | 2 | 3.44 | 54.8 | 0.684 | 0.315 | 1533 |
器件实施例3 | 3 | 3.39 | 54.2 | 0.687 | 0.312 | 1529 |
器件实施例4 | 6 | 3.55 | 55.2 | 0.685 | 0.314 | 1532 |
器件实施例5 | 10 | 3.41 | 54.6 | 0.684 | 0.315 | 1533 |
器件实施例6 | 17 | 3.45 | 55.0 | 0.686 | 0.313 | 1530 |
器件实施例7 | 37 | 3.53 | 54.9 | 0.685 | 0.314 | 1531 |
器件实施例8 | 38 | 3.49 | 55.1 | 0.687 | 0.312 | 1527 |
器件实施例9 | 39 | 3.53 | 55.4 | 0.687 | 0.312 | 1529 |
器件实施例10 | 40 | 3.47 | 55.7 | 0.687 | 0.312 | 1525 |
器件实施例11 | 43 | 3.45 | 55.6 | 0.687 | 0.312 | 1526 |
器件实施例12 | 46 | 3.44 | 54.4 | 0.685 | 0.314 | 1532 |
器件实施例13 | 52 | 3.43 | 54.1 | 0.686 | 0.313 | 1530 |
器件实施例14 | 64 | 3.55 | 55.4 | 0.686 | 0.313 | 1524 |
器件实施例15 | 65 | 3.44 | 55.1 | 0.684 | 0.315 | 1533 |
器件实施例16 | 66 | 3.52 | 55.8 | 0.685 | 0.314 | 1531 |
器件实施例17 | 73 | 3.46 | 55.4 | 0.686 | 0.313 | 1524 |
器件实施例18 | 85 | 3.42 | 54.7 | 0.687 | 0.312 | 1527 |
器件实施例19 | 94 | 3.39 | 55.3 | 0.687 | 0.312 | 1525 |
器件实施例20 | 100 | 3.44 | 55.2 | 0.685 | 0.314 | 1524 |
器件实施例21 | 125 | 3.50 | 54.0 | 0.684 | 0.315 | 1524 |
器件实施例22 | 126 | 3.53 | 53.8 | 0.686 | 0.313 | 1521 |
器件实施例23 | 129 | 3.48 | 53.9 | 0.687 | 0.312 | 1520 |
器件实施例24 | 132 | 3.48 | 53.6 | 0.684 | 0.315 | 1521 |
器件实施例25 | 133 | 3.43 | 53.7 | 0.685 | 0.314 | 1526 |
器件实施例26 | 142 | 3.54 | 53.4 | 0.687 | 0.312 | 1525 |
器件实施例27 | 161 | 3.46 | 53.7 | 0.684 | 0.315 | 1521 |
器件实施例28 | 162 | 3.51 | 53.4 | 0.685 | 0.314 | 1525 |
器件实施例29 | 208 | 3.48 | 53.8 | 0.685 | 0.314 | 1521 |
器件实施例30 | 251 | 3.42 | 52.2 | 0.686 | 0.313 | 1519 |
器件实施例31 | 252 | 3.47 | 53.2 | 0.687 | 0.312 | 1520 |
器件实施例32 | 254 | 3.49 | 53.4 | 0.687 | 0.312 | 1515 |
器件实施例33 | 255 | 3.42 | 52.0 | 0.686 | 0.313 | 1516 |
器件实施例34 | 259 | 3.45 | 53.0 | 0.686 | 0.313 | 1519 |
器件实施例35 | 260 | 3.40 | 52.7 | 0.686 | 0.313 | 1522 |
器件实施例36 | 261 | 3.53 | 52.8 | 0.684 | 0.315 | 1521 |
器件实施例37 | 290 | 3.53 | 52.7 | 0.684 | 0.315 | 1519 |
器件实施例38 | 305 | 3.49 | 52.6 | 0.684 | 0.315 | 1513 |
器件实施例39 | 317 | 3.39 | 53.0 | 0.687 | 0.312 | 1513 |
器件实施例40 | 322 | 3.54 | 53.4 | 0.687 | 0.312 | 1519 |
器件实施例41 | 323 | 3.50 | 52.3 | 0.684 | 0.315 | 1516 |
器件实施例42 | 386 | 3.49 | 51.8 | 0.686 | 0.313 | 1513 |
器件实施例43 | 394 | 3.49 | 51.5 | 0.686 | 0.313 | 1511 |
器件实施例44 | 396 | 3.49 | 52.0 | 0.686 | 0.313 | 1510 |
器件实施例45: 绿光有机电致发光器件制备
所制备OLED器件的结构为:ITO阳极/HIL/HTL/发光辅助层/EML /ETL /EIL/阴极/光取出层
a、ITO阳极:将涂层厚度为1500Å的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,用甲醇、丙酮、异丙醇依次超声波洗涤(每次洗涤5 min),干燥,然后转移至等离子体清洗机内洗涤5min,再送至蒸镀机中,以该基板为阳极,在其上依次蒸镀其它功能层。
b、HIL(空穴注入层):以1Å/s的蒸镀速率,真空蒸镀空穴注入层材料HT和P-dopant,其化学式如下所示;所述HT和P-dopant的蒸镀速率比为97:3,厚度为10nm;
c、HTL(空穴传输层):以1.5Å/s的蒸镀速率,在空穴注入层上面真空蒸镀130nm的HT作为空穴传输层;
d、发光辅助层:以0.5Å/s的蒸镀速率,在空穴传输层上面真空蒸镀10nm的上述实施例提供的化合物5作为发光辅助层;
e、EML(发光层):然后在上述发光辅助层上,以1Å/s的蒸镀速率,真空蒸镀厚度为200nm的双主体材料(Host1和Host2)和掺杂材料(Dopant)作为发光层,其Host1和Host2比例为50:50。其Host1、Host2和Dopant的化学式如下所示;其中双Host和Dopant的蒸镀速率比为98:2。
f、HBL(空穴阻挡层):以0.5Å/s的蒸镀速率,真空蒸镀厚度为5.0nm的空穴阻挡层HB。
g、ETL(电子传输层):以1Å/s的蒸镀速率,真空蒸镀厚度为35nm的ET和Liq作为电子传输层,其ET的化学式如下所示;其中ET和Liq的蒸镀速率比为50:50。
h、EIL(电子注入层):以0.5Å/s的蒸镀速率,蒸镀Yb膜层1.0nm,形成电子注入层。
i、阴极:以1Å/s的蒸镀速率比,蒸镀镁和银 18nm,其蒸镀速率比为1:9,得到OLED器件。
j、光取出层:以1Å/s的蒸镀速率,在阴极上真空蒸镀厚度为70nm的CPL,作为光取出层。
K、随后将蒸镀完成的基板进行封装。首先采用涂胶设备将清洗后盖板用UV胶进行涂覆工艺,然后将涂覆完成的盖板移至压合工段,将蒸镀完成的基板置于盖板上端,最后将基板和盖板在贴合设备作用下进行贴合,同时完成对UV胶光照固化。
。
参照上述器件实施例45提供的方法,分别选用化合物10、11、12、13、17、19、39、40、41、42、45、48、49、59、60、71、72、75、77、103、115、124、127、137、138、139、140、151、152、153、160、165、172、174、231、270、287、288、291、292、293、294、306、328、329、345、387、405、425、426替代化合物5,进行发光辅助层的蒸镀,并制备得到相应的有机电致发光器件,分别记为器件实施例46-95。
器件对比例8-14:
该对比例提供了一种有机电致发光器件,该有机电致发光器件的制备方法与器件实施例45的唯一区别在于,该有机电致发光器件是采用现有的对比化合物a、b、c、d、e、f、g替代上述器件实施例45中的发光辅助材料(化合物5)进行蒸镀。其中,对比化合物a、b、c、d、e、f、g的化学结构式如下:
。
在15000(nits)亮度下对上述器件实施例45~95以及器件对比例8-14得到的有机电致发光器件的驱动电压、发光效率以及寿命进行表征,测试结果如下表3:
表3:
有机电致发光器件 | 发光辅助材料 | 驱动电压(V) | 发光效率(cd/A) | CIEx | CIEy | T95寿命(h) |
对比例8 | 化合物a | 3.69 | 151.0 | 0.245 | 0.714 | 825 |
对比例9 | 化合物b | 3.70 | 150.5 | 0.246 | 0.713 | 830 |
对比例10 | 化合物c | 3.73 | 151.6 | 0.243 | 0.716 | 833 |
对比例11 | 化合物d | 3.71 | 152.8 | 0.245 | 0.714 | 848 |
对比例12 | 化合物e | 3.76 | 152.1 | 0.245 | 0.714 | 844 |
对比例13 | 化合物f | 3.73 | 151.6 | 0.246 | 0.713 | 840 |
对比例14 | 化合物g | 3.74 | 151.4 | 0.246 | 0.713 | 838 |
器件实施例45 | 5 | 3.46 | 168.1 | 0.245 | 0.715 | 917 |
器件实施例46 | 10 | 3.53 | 167.7 | 0.246 | 0.713 | 902 |
器件实施例47 | 11 | 3.60 | 169.2 | 0.244 | 0.716 | 917 |
器件实施例48 | 12 | 3.55 | 167.7 | 0.244 | 0.716 | 902 |
器件实施例49 | 13 | 3.58 | 170.2 | 0.244 | 0.714 | 901 |
器件实施例50 | 17 | 3.52 | 169.8 | 0.245 | 0.714 | 905 |
器件实施例51 | 19 | 3.49 | 171.3 | 0.244 | 0.715 | 911 |
器件实施例52 | 39 | 3.55 | 172.0 | 0.244 | 0.715 | 908 |
器件实施例53 | 40 | 3.59 | 172.3 | 0.244 | 0.715 | 899 |
器件实施例54 | 41 | 3.58 | 171.7 | 0.245 | 0.714 | 902 |
器件实施例55 | 42 | 3.62 | 169.4 | 0.243 | 0.714 | 902 |
器件实施例56 | 45 | 3.55 | 173.1 | 0.245 | 0.714 | 901 |
器件实施例57 | 48 | 3.59 | 171.1 | 0.243 | 0.714 | 900 |
器件实施例58 | 49 | 3.63 | 171.8 | 0.244 | 0.714 | 902 |
器件实施例59 | 59 | 3.57 | 169.7 | 0.246 | 0.713 | 911 |
器件实施例60 | 60 | 3.50 | 170.1 | 0.245 | 0.713 | 905 |
器件实施例61 | 71 | 3.61 | 168.1 | 0.245 | 0.713 | 909 |
器件实施例62 | 72 | 3.62 | 173.2 | 0.245 | 0.716 | 912 |
器件实施例63 | 75 | 3.54 | 172.1 | 0.244 | 0.716 | 898 |
器件实施例64 | 77 | 3.47 | 171.9 | 0.243 | 0.714 | 916 |
器件实施例65 | 103 | 3.62 | 170.1 | 0.243 | 0.713 | 902 |
器件实施例66 | 115 | 3.48 | 172.6 | 0.244 | 0.715 | 915 |
器件实施例67 | 124 | 3.59 | 165.7 | 0.244 | 0.715 | 891 |
器件实施例68 | 127 | 3.61 | 166.5 | 0.243 | 0.714 | 893 |
器件实施例69 | 137 | 3.49 | 166.6 | 0.244 | 0.713 | 884 |
器件实施例70 | 138 | 3.47 | 167.0 | 0.244 | 0.716 | 895 |
器件实施例71 | 139 | 3.57 | 166.8 | 0.245 | 0.713 | 892 |
器件实施例72 | 140 | 3.55 | 167.1 | 0.246 | 0.714 | 896 |
器件实施例73 | 151 | 3.52 | 167.3 | 0.246 | 0.713 | 899 |
器件实施例74 | 152 | 3.56 | 165.7 | 0.243 | 0.716 | 884 |
器件实施例75 | 153 | 3.60 | 165.7 | 0.246 | 0.713 | 894 |
器件实施例76 | 160 | 3.62 | 167.1 | 0.243 | 0.716 | 900 |
器件实施例77 | 165 | 3.48 | 166.5 | 0.245 | 0.713 | 882 |
器件实施例78 | 172 | 3.63 | 166.6 | 0.246 | 0.714 | 883 |
器件实施例79 | 174 | 3.46 | 166.9 | 0.244 | 0.715 | 883 |
器件实施例80 | 231 | 3.46 | 167.4 | 0.244 | 0.715 | 884 |
器件实施例81 | 270 | 3.46 | 160.2 | 0.245 | 0.714 | 891 |
器件实施例82 | 287 | 3.47 | 164.7 | 0.243 | 0.716 | 874 |
器件实施例83 | 288 | 3.62 | 164.0 | 0.246 | 0.713 | 870 |
器件实施例84 | 291 | 3.56 | 160.2 | 0.244 | 0.716 | 865 |
器件实施例85 | 292 | 3.61 | 160.3 | 0.245 | 0.714 | 866 |
器件实施例86 | 293 | 3.59 | 165.5 | 0.244 | 0.716 | 868 |
器件实施例87 | 294 | 3.59 | 162.8 | 0.244 | 0.713 | 875 |
器件实施例88 | 306 | 3.53 | 162.3 | 0.246 | 0.716 | 871 |
器件实施例89 | 328 | 3.62 | 165.3 | 0.245 | 0.714 | 882 |
器件实施例90 | 329 | 3.62 | 164.2 | 0.243 | 0.716 | 878 |
器件实施例91 | 345 | 3.57 | 161.9 | 0.246 | 0.715 | 868 |
器件实施例92 | 387 | 3.56 | 159.1 | 0.243 | 0.715 | 869 |
器件实施例93 | 405 | 3.54 | 159.5 | 0.245 | 0.714 | 870 |
器件实施例94 | 425 | 3.57 | 159.3 | 0.245 | 0.713 | 867 |
器件实施例95 | 426 | 3.53 | 160.1 | 0.244 | 0.716 | 865 |
从表2和表3可以看出,无论是绿光器件还是红光器件,通过变换取代基以及取代基的位置不同,都会使器件的性能有所改变。使用本发明提供的发光辅助材料制备的有机电致发光器件与对比例化合物制备的有机电致发光器件相比较而言,器件的效率和寿命均得到提高。
本发明化合物10、17、322与对比化合物e、f、g、d为平行对比例。
对比化合物c和本发明化合物1相比,其区别在于:对比化合物c中2个芴上的其中一个9位都分别是被苯基取代,而本发明化合物1中2个芴上的其中一个9位都分别是被甲基所取代的。因为芴结构中心碳原子为SP3杂化,不参与共轭,因此芴结构中除去与N相连的苯基之外的基团对材料电子性能影响较弱。本发明与对比化合物相比,以甲基代替9,9二苯基芴的苯环结构,降低了分子量,减小了结构刚性,使得蒸镀温度得以降低,提高了材料蒸镀过程中的稳定性,增加器件寿命。
Claims (7)
1.一种发光辅助材料,其特征在于,具有化学式I所示结构:
;
化学式I中,
R1、R2、R3、R4分别独立表示氢;
R5、R6分别独立表示氢、甲基、苯基;
Ar独立表示以下基团:
;其中,
R11~R25可以相同也可以不同,独立表示氢、苯基;
R26独立表示苯基、联苯基;
R27独立表示亚苯基、亚联苯基。
2.根据权利要求1所述的发光辅助材料,其特征在于,化学式I的结构通式为:
;
其中上述化学式-I-1~化学式-I-9中R1-R4、Ar如权利要求1中所述定义。
3.一种发光辅助材料,其特征在于,所述发光辅助材料选自以下结构:
/>/>/>/>/>/>/>/>/>/>/>/>/>/> />/>。
4.一种如权利要求1所述发光辅助材料的制备方法,其特征在于,所述方法具体包括如下步骤:
步骤1、中间体1的制备
将原料A 1.0eq溶于甲苯中,原料B 1.2eq溶于甲苯中,随后将原料B溶液缓慢滴加到原料A溶液中;接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯0.01eq,三叔丁基膦0.05eq及叔丁醇钠2.0eq,搅拌均匀,升温至80℃-120℃,并回流反应4-12h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂三(二亚苄基丙酮)二钯,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用体积比为1:10的二氯甲烷和石油醚的混合溶液,通过柱色谱法纯化,除去杂质,从而获得中间体1;
步骤2、化学式I的制备
将中间体1 1.0eq溶于甲苯中,原料C 1.0eq溶于甲苯中,随后将原料C溶液缓慢滴加到中间体1溶液中。接着换气3次,氮气保护下加入三(二亚苄基丙酮)二钯0.01eq,三叔丁基膦0.05eq及叔丁醇钠2.0eq,搅拌均匀,升温至80℃-120℃,并回流反应4-12h;反应结束后,降温至50℃,使用硅藻土进行过滤,除去盐以及催化剂三(二亚苄基丙酮)二钯,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用体积比为1:6的二氯甲烷和石油醚的混合溶液,通过柱色谱法纯化剩余物质获得化学式I;
具体合成路线如下:
;
其中,R1-R6、Ar如上述化学式Ⅰ中所述定义,Hal1-Hal2各自独立的选自氯、溴或碘。
5.一种如权利要求1所述发光辅助材料或如权利要求4所述方法制备的发光辅助材料在有机电致发光器件中的应用。
6.根据权利要求5所述的应用,其特征在于,所述有机电致发光器件,包括第一电极、第二电极以及至少一层设置在所述第一电极和所述第二电极之间的有机物层。
7.根据权利要求6所述的应用,其特征在于,所述有机物层包括所述发光辅助材料。
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