CN110642842B - 化合物、显示面板以及显示装置 - Google Patents
化合物、显示面板以及显示装置 Download PDFInfo
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- CN110642842B CN110642842B CN201910939761.6A CN201910939761A CN110642842B CN 110642842 B CN110642842 B CN 110642842B CN 201910939761 A CN201910939761 A CN 201910939761A CN 110642842 B CN110642842 B CN 110642842B
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- 125000003118 aryl group Chemical group 0.000 abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 10
- 125000001424 substituent group Chemical group 0.000 abstract description 10
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract description 8
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract description 8
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 4
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- 125000006736 (C6-C20) aryl group Chemical group 0.000 abstract description 3
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 3
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 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
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
本发明涉及OLED技术领域并提供具有TADF性质的化合物。化合物的结构如化学式1所示;Ar表示C6‑C20芳基或C5‑C20杂芳基;D1和D2表示给电子基团,A1和A2表示受电子基团,m、n、p、q各自独立地选自1、2、3;D1、D2、A1和A2分别连接到与Ar连接的苯环上;D1和D2各自独立地选自C1‑C20烷基、C3‑C20环烷基、C1‑C20烷氧基、C3‑C20杂环基、C6‑C40芳基、C4‑C40杂芳基、C10‑C60的稠芳基、C10‑C60的稠杂芳基、咔唑类基团、二苯胺类基团、吖啶基类基团中的至少一种;A1和A2各自独立地选自含氮杂环类取代基、含氰基类取代基、含羰基类取代基、砜类取代基和含磷氧基类取代基。本发明的化合物适合用作OLED的发光主体材料或客体材料。本发明还提供一种包括所述化合物的显示面板和显示装置。
Description
技术领域
本发明涉及有机电致发光材料技术领域,具体地涉及一种具有TADF 性质的化合物以及包括该化合物的显示面板以及显示装置。
背景技术
随着电子显示技术的发展,有机发光器件(OLED)广泛应用于各种显示设备中,对OLED的发光材料的研究和应用也日益增多。
根据发光机制,用于OLED发光层的材料主要包括以下四种:
(1)荧光材料;(2)磷光材料;(3)三线态-三线态湮灭(TTA)材料0;(4)热活化延迟荧光(TADF)材料。
对于荧光材料,根据自旋统计,激子中单线态和三线态激子的比例是 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,光取出效率为20%左右,因此基于荧光材料的OLED的外量子效应(EQE)不超过5%。
对于磷光材料,磷光材料由于重原子效应,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,光取出效率为20%左右,因此基于磷光材料的OLED的外量子效应可以达到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。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。
对于三线态-三线态湮灭(TTA)材料,两个相邻的三线态激子,复合生成一个更高能级的单线激发态分子和一个基态分子,但是两个三线态激子产生一个单线态激子,所以理论最大内量子产率只能达到62.5%。为了防止产生较大的效率滚降现象,在这个过程中三线态激子的浓度需要调控。
对于热激活延迟荧光(TADF)材料,当单线激发态和三线激发态的能级差较小时,分子内部发生反向系间窜越(RISC),T1态激子通过吸收环境热上转换到S1态,可以同时利用75%的三线态激子和25%的单线态激子,理论最大内量子产率可达100%。TADF材料主要为有机化合物,不需要稀有金属元素,生产成本低。TADF材料可以通过多种方法进行化学修饰。但目前已发现的TADF材料较少,因此亟待开发新型的可用于OLED的 TADF材料。
发明内容
有鉴于此,本发明提供一种具有热活化延迟荧光(TADF)性质的化合物,所述化合物具有化学式1所示的结构:
Ar表示C6-C20芳基或C5-C20杂芳基;
D1和D2表示给电子基团,m和n各自独立地选自1、2、3;
A1和A2表示受电子基团,p和q各自独立地选自1、2、3;
D1、D2、A1和A2分别连接到与Ar连接的苯环上;D1、D2、A1和A2与苯环的连接位置可以是两两之间各自彼此相邻的位置,也可以是两两之间各自彼此相间的位置(对角线的位置)。
D1和D2各自独立地选自取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的 C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40 杂芳基、取代或未取代的C10-C60的稠芳基、取代或未取代的C10-C60 的稠杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、C13-C40的吖啶基及其衍生物基团中的至少一种;
A1和A2各自独立地选自含氮杂环类取代基、含氰基类取代基、含羰基类取代基、砜类取代基和含磷氧基类取代基。
本发明的化合物中心的Ar基团通过Ar外围的四个苯环连接给电子基团D和受电子基团A的连接基团,使整个分子同时具有给电子单元和受电子单元,对空穴和电子具有较为平衡的传输效果,形成双极性主体材料。当双极性主体材料作为发光层的主体材料时,能够有效地拓宽发光区,提升发光效率,延长器件寿命。
另外,给电子单元D和受电子单元A位于同一个分子中,带来HOMO 与LUMO的有效分离,形成较低的△EST,有效提升反向系间穿越过程。本发明的化合物不仅可以通过化学键形成分子内的电荷转移作用,同时由于同一个分子中的给电子单元D和受电子单元A具有较近的空间距离,因此也会形成空间电荷转移作用,可以作为TADF发光材料。本发明所述的具有TADF效应的化合物用作主体材料时,可以有效地提升三线态激子的利用效率,提升发光主体材料和发光客体材料之间的能量转移过程,提升OLED器件的发光效率,提升器件的工作寿命。
附图说明
图1是本发明实施例提供的代表性化合物P1的化学结构;
图2是本发明实施例提供的代表性化合物P39的HOMO分布图;
图3是本发明实施例提供的一种OLED的结构示意图;
图4是本发明实施例提供的一种显示装置的示意图。
具体实施方式
下面通过实施例和对比例进一步说明本发明,这些实施例只是用于说明本发明,本发明不限于以下实施例。
本发明的一方面提供一种化合物,所述化合物具有化学式1所示的结构:
Ar表示C6-C20芳基或C5-C20杂芳基;
D1和D2表示给电子基团,m和n各自独立地选自1、2、3;
A1和A2表示受电子基团,p和q各自独立地选自1、2、3;
D1、D2、A1和A2分别连接到与Ar连接的苯环上;
D1和D2各自独立地选自取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的 C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C4-C40 杂芳基、取代或未取代的C10-C60的稠芳基、取代或未取代的C10-C60 的稠杂芳基、取代或未取代的C12-C40的咔唑基及其衍生物基团、取代或未取代的C12-C40的二苯胺基及其衍生物基团、C13-C40的吖啶基及其衍生物基团中的至少一种;
A1和A2各自独立地选自含氮杂环类取代基、含氰基类取代基、含羰基类取代基、砜类取代基和含磷氧基类取代基。
根据本发明所述化合物的一个实施方式,所述化合物具有如下所示的任一种化学结构:
根据本发明所述化合物的一个实施方式,所述化合物具有如下所示的任一种化学结构:
根据本发明所述化合物的一个实施方式,A1和A2相同,且D1和D2相同。在A1和A2相同且D1和D2相同的情况下,化合物呈对称结构,因此更容易合成,从而带来更低的生产成本。
根据本发明所述化合物的一个实施方式,D1和D2各自独立地选自以下基团中的任意一种:
其中,#表示在化学式1中的连接位置,R表示C1-C20烷基、C1-C20 烷氧基、C2-C20烯基、C2-C20炔基、C6-C40芳香基、C4-C40杂芳香基。
根据本发明所述化合物的一个实施方式,D1和D2各自独立地选自以下基团中的任意一种:
其中,#表示在化学式1中的连接位置。
根据本发明所述化合物的一个实施方式,D1和D2各自独立地选自以下基团中的任意一种:
其中,#表示在化学式1中的连接位置。
根据本发明所述化合物的一个实施方式,D1和D2各自独立地选自以下基团中的任意一种:
其中,#表示在化学式1中的连接位置;R表示C1-C20烷基、C1-C20 烷氧基、C2-C20烯基、C2-C20炔基、C6-C40芳香基、C4-C40杂芳香基。
根据本发明所述化合物的一个实施方式,所述含氮杂环类基团选自以下基团中的任意一种:
其中,#表示在化学式1中的连接位置;
R选自氢原子、C1-C20烷基、C1-C20烷氧基、C4-C8环烷基、C6-C40 芳基、C4-C40杂芳基。
根据本发明所述化合物的一个实施方式,所述含氰基类基团选自以下基团中的任意一种:
其中,#表示在化学式1中的连接位置。
根据本发明所述化合物的一个实施方式,所述含羰基类基团选自以下基团中的任意一种:
其中,#表示在化学式1中的连接位置,R表示C1-C20烷基、C1-C20 烷氧基、C2-C20烯基、C2-C20炔基、C4-C8环烷基、C6-C40芳香基、C4-C40 杂芳基。
根据本发明所述化合物的一个实施方式,所述含砜类基团选自以下基团中的任意一种:
根据本发明所述化合物的一个实施方式,所述含膦氧基团选自以下基团中的任意一种:
所述X选自O、S、-BR41、-C(R41)2、-Si(R41)2和-NR41中的任意一种;
所述R30、R31、R32、R33、R34、R35、R36、R37、R38、R39、R40、R41均各自独立地选自氢原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的 C3-C20杂环基、取代或未取代的C6-C40芳基、取代或未取代的C2-C40 杂芳基中的任意一种;
#表示在化学式1中的连接位置。
根据本发明所述化合物的一个实施方式,所述化合物选自下列化合物:
根据本发明所述化合物的一个实施方式,所述化合物的最低单重态能级S1与最低三重态能级T1之间的能级差ΔEST=ES1-ET1≦0.30eV。
本发明的化合物具备TADF特性,可以用作OLED发光层的主体材料或客体材料。
本发明还提供了示例性化合物P7、P39、P66、P71、P103的制备方法,如下所述。在本发明中,各合成实例中用到的中间体S1、S2、S5、S7、 S8、S11、S12、S14、S18、S19、S21、S22、S23、S25和S26来自于市售商品。
化合物P7的合成
在-78℃的条件下,将S1(1.8mmol)溶解在乙醚(100mL)中,向溶液中逐滴滴入n-BuLi(1.95mmol)的正己烷溶液。反应溶液持续搅拌2 h,缓慢升温至室温,在室温下搅拌1h。再次将反应溶液冷却至-78℃,在搅拌的条件下,逐滴加入45mL S2(2.2mmol)的甲苯溶液。缓慢升温至室温搅拌过夜。减压蒸馏去除所有的溶剂,收集粗产物。将粗产品分别用甲醇(3×40mL)和戊烷(3×40mL)清洗,再次收集粗产物。粗产物通过硅胶色谱柱纯化,以正己烷:三氯甲烷(6:1)作为洗脱剂,最后纯化得到S3(0.97mmol,54%)。
MALDI-TOF MS:C24H17B2Br,m/z计算值:406.1;测量值:406.3。
在100ml三口烧瓶中,首先将S3(1.5mmol)、联硼酸频那醇酯(1.8 mmol)、(1,1’-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.04mmol)以及乙酸钾 (10mmol)分别加入,一边搅拌,一边迅速反复3次脱气和氮气置换,通过注射器加入6mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入5ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S4(1.2mmol,80%)。
MALDI-TOF MS:C30H29B3O2,m/z计算值:454.2;测量值:454.5。
在氮气保护下,称取化合物S5(4.5mmol)、S4(9.6mmol)、 [Pd2(dba)3]·CHCl3(0.18mmol)和HP(tBu)3·BF4(0.36mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入80mL甲苯(提前通N2 15min除氧气),然后再逐滴加入8mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入20mL去离子水,再滴入几滴2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S6(3.4mmol,75%)。
MALDI-TOF MS:C54H36B4Br2,m/z计算值:887.9;测试值:888.2。
将S7(2.5mmol)、S8(2.6mmol)、(二亚苄基丙酮)二钯(0)(0.12mmol)、叔丁醇钠(4mmol)、四氟硼酸三叔丁基膦(0.25mmol)投入100mL三口烧瓶中,一边搅拌,一边迅速反复3次脱气和氮气置换,通过注射器加入40mL甲苯。将该混合物在氮气气流下,加热回流3小时。反应后,在放置冷却至室温的反应溶液中添加水,利用二氯甲烷进行萃取,并利用饱和食盐水进行洗净。利用无水硫酸钠对有机层进行干燥后,将溶剂蒸馏去除,并使用柱层析法进行精制,获得中间体S9(1.85mmol、74%)。
MALDI-TOF MS:C21H18BrN,m/z计算值:363.1;测试值:363.4。
在100ml三口烧瓶中,首先将S9(1.8mmol)、联硼酸频那醇酯(2.2 mmol)、(1,1’-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.05mmol)以及乙酸钾 (12mmol)分别加入,一边搅拌,一边迅速反复3次脱气和氮气置换,通过注射器加入8mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入6ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S10(1.4mmol,78%)。
MALDI-TOF MS:C27H30BNO2,m/z计算值:411.2;测量值:411.3。
在氮气保护下,称取化合物S6(2.0mmol)、S4(4.5mmol)、 [Pd2(dba)3]·CHCl3(0.08mmol)和HP(tBu)3·BF4(0.16mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入80mL甲苯(提前通N2 15min除氧气),然后再逐滴加入8mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入20mL去离子水,再滴入几滴2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P7(1.4mmol,70%)。
MALDI-TOF MS:C96H72B4N2,m/z计算值:1296.6;测试值:1296.8。
元素分析结果:C,88.91;H,5.60;B,3.33;N,2.16;测试值:C,88.94;H, 5.61;B,3.31;N,2.14。
化合物P39的合成
在氮气保护下,称取化合物S11(3.5mmol)、S12(3.8mmol), [Pd2(dba)3]·CHCl3(0.15mmol)和HP(tBu)3·BF4(0.3mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入25mL甲苯(提前通N2 15min除氧气),然后再逐滴加入3mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入25mL去离子水,再滴入几滴2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S13(2.4mmol,68%)。
MALDI-TOF MS:C21H18BN3O2,m/z计算值:355.2;测试值:355.5。
将S1(2.25mmol)、S14(2.35mmol)、(二亚苄基丙酮)二钯(0)(0.12 mmol)、叔丁醇钠(3.6mmol)、四氟硼酸三叔丁基膦(0.25mmol)投入 100mL三口烧瓶中,一边搅拌,一边迅速反复3次脱气和氮气置换,通过注射器加入35mL甲苯。将该混合物在氮气气流下,加热回流3小时。反应后,在放置冷却至室温的反应溶液中添加水,利用二氯甲烷进行萃取,并利用饱和食盐水进行洗净。利用无水硫酸钠对有机层进行干燥后,将溶剂蒸馏去除,并使用柱层析法进行精制,获得中间体S15(1.73mmol、77%)。
MALDI-TOF MS:C24H24BNO2,m/z计算值:369.2;测试值:369.5。
在100ml三口烧瓶中,首先将S15(1.35mmol)、联硼酸频那醇酯(1.65 mmol)、(1,1’-双(二苯基膦)二茂铁)二氯钯(Ⅱ)(0.05mmol)以及乙酸钾 (9mmol)分别加入,一边搅拌,一边迅速反复3次脱气和氮气置换,通过注射器加入6mL四氢呋喃。在一定转速下搅拌,将所得的混合溶液反应物在反应温度80℃下加热回流5h;待反应结束后,冷却至室温并加入 6ml水,用乙醚萃取,将所得有机相用无水硫酸钠干燥,将溶剂蒸馏去除,并使用柱层析法进行精制,得到中间体S10(1.1mmol,81%)。
MALDI-TOF MS:C24H24BNO2,m/z计算值:369.2;测量值:369.3。
在氮气保护下,称取化合物S5(3.6mmol)、S16(7.8mmol)、 [Pd2(dba)3]·CHCl3(0.15mmol)和HP(tBu)3·BF4(0.30mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入6.5mL浓度为1M的K2CO3水溶液(提前通N2 15min除氧气),室温搅拌过夜。反应结束后,加入25mL去离子水,再滴入几滴 2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S17(2.5mmol,69%)。
MALDI-TOF MS:C42H26Br2N2:m/z计算值:716.0;测试值:716.2。
在氮气保护下,称取化合物S17(1.2mmol)、S13(2.7mmol)、 [Pd2(dba)3]·CHCl3(0.06mmol)和HP(tBu)3·BF4(0.12mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入50mL甲苯(提前通N2 15min除氧气),然后再逐滴加入6mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入15mL去离子水,再滴入几滴2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P39(0.8mmol,66%)。
MALDI-TOF MS:C72H38N8,m/z计算值:1014.3;测试值:1014.5。
元素分析结果:C,85.19;H,3.77;N,11.04;测试值:C,85.21;H,3.76; N,11.01。
化合物P66的合成
在氮气保护下,称取化合物S18(2.2mmol)、S19(4.8mmol)、 [Pd2(dba)3]·CHCl3(0.10mmol)和HP(tBu)3·BF4(0.20mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入70mL甲苯(提前通N2 15min除氧气),然后再逐滴加入5mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入20mL去离子水,再滴入几滴2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S20(1.5mmol,68%)。
MALDI-TOF MS:C42H26Br2N2:m/z计算值:716.0;测试值:716.3。
在氮气保护下,称取化合物S20(1.8mmol)、S21(3.9mmol)、 [Pd2(dba)3]·CHCl3(0.10mmol)和HP(tBu)3·BF4(0.20mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入60mL甲苯(提前通N2 15min除氧气),然后再逐滴加入5mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入15mL去离子水,再滴入几滴2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P66(1.3mmol,72%)。
MALDI-TOF MS:C84H54N8,m/z计算值:1174.4;测试值:1174.5。
元素分析结果:C,85.84;H,4.63;N,9.53;测试值:C,85.86;H,4.64;N, 9.50。
化合物P71的合成
在氮气保护下,称取化合物S22(2.5mmol)、S23(5.5mmol)、 [Pd2(dba)3]·CHCl3(0.12mmol)和HP(tBu)3·BF4(0.24mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入80mL甲苯(提前通N2 15min除氧气),然后再逐滴加入5.8mL浓度为1M的K2CO3水溶液(提前通N2 15min除氧气),室温搅拌过夜。反应结束后,加入25mL去离子水,再滴入几滴 2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S24(1.9mmol,76%)。
MALDI-TOF MS:C42H26Br2N2:m/z计算值:716.0;测试值:716.3。
在氮气保护下,称取化合物S24(3.3mmol)、S25(7.2mmol)、 [Pd2(dba)3]·CHCl3(0.15mmol)和HP(tBu)3·BF4(0.30mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入100mL甲苯(提前通N2 15min除氧气),然后再逐滴加入8mL浓度为1M的K2CO3水溶液(提前通N2 15min除氧气),室温搅拌过夜。反应结束后,加入30mL去离子水,再滴入几滴2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P71(2.7mmol,82%)。
MALDI-TOF MS:C79H51N3O2:m/z计算值:1073.4;测试值:1075.6。
元素分析结果:C,88.32;H,4.79;N,3.91;O,2.98;测试值:C,88.35;H, 4.81;N,3.89;O,2.95。
化合物P103的合成
在氮气保护下,称取化合物S26(1.5mmol)、S4(3.2mmol)、 [Pd2(dba)3]·CHCl3(0.08mmol)和HP(tBu)3·BF4(0.15mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入50mL甲苯(提前通N2 15min除氧气),然后再逐滴加入3.5mL浓度为1M的K2CO3水溶液(提前通N2 15min除氧气),室温搅拌过夜。反应结束后,加入15mL去离子水,再滴入几滴 2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体S27(1.2mmol,80%)。
MALDI-TOF MS:C58H38B4Br2:m/z计算值:936.2;测试值:936.3。
在氮气保护下,称取化合物S27(1.3mmol)、S10(2.9mmol)、 [Pd2(dba)3]·CHCl3(0.08mmol)和HP(tBu)3·BF4(0.16mmol),加入到250mL 的两口烧瓶中。向两口烧瓶内注入40mL甲苯(提前通N2 15min除氧气),然后再逐滴加入4mL浓度为1M的K2CO3水溶液(提前通N215min除氧气),室温搅拌过夜。反应结束后,加入15mL去离子水,再滴入几滴2M HCl。用二氯甲烷萃取,收集有机相,并用无水Na2SO4干燥处理。过滤干燥后的溶液,用旋转蒸发仪除去溶剂,得到粗产物。粗产物通过硅胶色谱柱纯化,最后纯化得到固体P103(0.98mmol,75%)。
MALDI-TOF MS:C100H74B4N2:m/z计算值:1346.6;测试值:1346.8。
元素分析结果:C,89.17;H,5.54;B,3.21;N,2.08;测试值:C,89.19;H, 5.57;B,3.18;N,2.06。
实施例1-8
运用密度泛函理论(DFT),针对化合物P7、P14、P30、P39、P48、 P56、P86、P89、P103,利用Gaussian 09程序包在B3LYP/6-31G(d)计算水平下,优化并计算得到了分子前线轨道HOMO和LUMO的分布情况;同时基于含时密度泛函理论(TDDFT),模拟计算了分子的单线态能级S1和三线态能级T1。
表1化合物的相关性能数据
注:S1表示单线态能级,T1表示三线态能级,Eg表示HOMO-LUMO能级差。
由表1可以看出,所有化合物的△EST均小于0.3ev,实现了较小的单线态和三线态能级差,具有TADF材料的特性,可以用作有机发光层的客体材料;同时本发明的化合物都具有高的单线态和三线态能级,也适于作为发光层中的主体材料。
本发明还提供一种显示面板,所述显示面板包括有机发光器件,其中所述有机发光器件包括相对设置的阳极、阴极,以及位于阳极和阴极之间的发光层,其中发光层的发光材料包括本发明所述的化合物中的一种或一种以上。
根据本发明的显示面板的一种实施方式,所述发光层的发光材料包括主体材料和客体材料,所述主体材料为本发明所述的化合物中的一种或一种以上。
根据本发明的显示面板的一种实施方式,所述发光层包括红色发光层,所述主体材料为红光主体材料。
根据本发明的显示面板的一种实施方式,所述发光层包括绿色发光层,所述主体材料为绿色主体材料。
根据本发明所述显示面板的一个实施方式,所述有机发光器件还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层或电子注入层中的一层或多层。
根据本发明的有机功能层还包括空穴注入层(HIL)、空穴传输层 (HTL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)中的一层或多层。
空穴注入材料、空穴传输材料及电子阻挡材料可选自2,2'-二甲基 -N,N'-二-1-萘基-N,N'-二苯基[1,1'-联苯]-4,4'-二胺(α-NPD)、4,4',4”-三(咔唑 -9-基)三苯胺(TCTA)、1,3-二咔唑-9-基苯(mCP)、4,4'-二(9-咔唑)联苯(CBP)、 3,3'-二(N-咔唑基)-1,1'-联苯(mCBP)、2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(HATCN)、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺(TAPC)、N,N'- 二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(α-NPB)、N,N'-二(萘-2-基)-N,N'- 二(苯基)联苯-4,4'-二胺(NPB)、聚(3,4-乙烯二氧噻吩)-聚苯乙烯磺酸 (PEDOT:PSS)、聚乙烯咔唑(PVK)、9-苯基-3,9-联咔唑(CCP)、三氧化钼 (MoO3)等材料,但不局限于以上几种材料。
空穴阻挡材料、电子传输材料、电子注入材料可选自2,8-二(二苯基氧膦基)二苯并噻吩(PPT)、TSPO1、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯 (TPBi)、2,8-双(二苯基膦氧基)二苯并呋喃(PPF)、二(2-二苯氧化膦基) 二苯醚(DPEPO)、氟化锂(LiF)、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶 (B3PYMPM)、4,7-二苯基-1,10-菲啰啉(Bphen)、1,3,5-三[(3-吡啶基)-3-苯基] 苯(TmPyBP)、三[2,4,6-三甲基-3-(3-吡啶基)苯基]硼烷(3TPYMB)、1,3-双 (3,5-二吡啶-3-基苯基)苯(B3PYPB)、1,3-双[3,5-二(吡啶-3-基)苯基]苯(BMPYPHB)、2,4,6-三(联苯基-3-基)-1,3,5-三嗪(T2T)、二苯基二[4-(吡啶-3- 基)苯基]硅烷(DPPS)、碳酸铯(Cs2O3)、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'- 联苯-4-羟基)铝(BAlq)、8-羟基喹啉-锂(Liq)、三(8-羟基喹啉)铝(Alq3)等材料,但不局限于以上几种材料。
在本发明提供的有机发光显示装置的一个实施方式中,所述发光层包括主体材料和客体材料,主体材料选自2,8-二(二苯基氧膦基)二苯并噻吩、 4,4'-二(9-咔唑)联苯、3,3'-二(N-咔唑基)-1,1'-联苯、2,8-双(二苯基膦氧基) 二苯并呋喃、双(4-(9H-咔唑基-9-基)苯基)二苯硅烷、9-(4-叔丁基苯基)-3,6- 双(三苯基甲硅烷基)-9H-咔唑、二(2-二苯氧化膦基)二苯醚、1,3-双[3,5-二 (吡啶-3-基)苯基]苯、4,6-双(3,5-二(3-吡啶)基苯基)-2-甲基嘧啶、9-(3-(9H- 咔唑基-9-基)苯基)-9H-咔唑-3-氰基、9-苯基-9-[4-(三苯基硅烷基)苯基]-9H- 芴、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯、二苯基[4-(三苯基硅烷基)苯基] 氧膦、4,4',4”-三(咔唑-9-基)三苯胺、2,6-二咔唑-1,5-吡啶、聚乙烯基咔唑和聚芴中的任意一种或一种以上,客体材料可选自荧光材料、磷光材料或热活化延迟荧光材料和聚集诱导发光材料中的一种或一种以上。
在本发明提供的显示面板中,有机发光器件的阳极材料可以选自金属例如铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金。阳极材料也可以选自金属氧化物如氧化铟、氧化锌、氧化铟锡(ITO)、氧化铟锌(IZO) 等;阳极材料还可以选自导电性聚合物例如聚苯胺、聚吡咯、聚(3-甲基噻吩)等。此外,阳极材料还可以选自除以列举的阳极材料以外的有助于空穴注入的材料及其组合,其包括已知的适合做阳极的材料。
在本发明提供的显示面板中,有机发光器件的阴极材料可以选自金属例如铝、镁、银、铟、锡、钛等及它们的合金。阴极材料也可以选自多层金属材料例如LiF/Al、LiO2/Al、BaF2/Al等。除了以上列举的阴极材料以外,阴极材料还可以是有助于电子注入的材料及其组合,包括已知的适合做阴极的材料。
有机发光器件可以按照本领域公知的方法进行制作,在此不再详述。在本发明中,有机发光器件可以这样制作:在透明或不透明的光滑的基板上形成阳极,在阳极上形成有机薄层,在有机薄层上形成阴极。有机薄层的形成可以采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明提供的有机电致发光器件如图3所示,包括:基板1、ITO阳极2、空穴注入层3、第一空穴传输层4、第二空穴传输层5、发光层6、第一电子传输层7、第二电子传输层8、阴极9(银电极)。
实施例9
本实施例提供一种有机电致发光器件,具体制备步骤如下:
1)将玻璃基板1切成50mm×50mm×0.7mm的大小,分别在丙酮、异丙醇和去离子水中超声清洁30分钟,然后将其在UV臭氧下清洁30分钟来进行清洁。将所得的具有氧化铟锡(ITO)阳极的玻璃基板安装到真空沉积设备上;
2)在ITO阳极层2上,通过真空蒸镀方式蒸镀空穴注入层材料化合物1作为空穴注入层3,厚度为10nm;
3)在空穴注入层3上真空蒸镀空穴传输层材料化合物2作为第一空穴传输层4,厚度为100nm;
4)在第一空穴传输层4上真空蒸镀空穴传输型材料化合物3作为第二空穴传输层5,厚度为10nm;
5)第二空穴传输层5上真空蒸镀一层发光层6,其中,本发明的化合物mCBP作为主体材料,化合物P7作为掺杂材料(客体材料),掺杂比例为3%(质量比),厚度为30nm;
6)在发光层6上真空蒸镀电子传输型材料化合物5作为第一电子传输层7,厚度为10nm;
7)电子传输层6上真空蒸镀电子传输材料化合物6作为第二电子传输层8,厚度为30nm;
8)第二电子传输层8上真空蒸镀银电极作为阴极9,厚度为15nm。
实施例10
本实施例与实施例9的区别在于,将化合物P7替换为P14。
实施例11
本实施例与实施例9的区别在于,将化合物P7替换为P30。
实施例12
本实施例与实施例9的区别在于,将化合物P7替换为P39。
实施例13
本实施例与实施例9的区别在于,将化合物P7替换为P48。
实施例14
本实施例与实施例9的区别在于,将化合物P7替换为P56。
实施例15
本实施例与实施例9的区别在于,将化合物P7替换为P86。
实施例16
本实施例与实施例9的区别在于,将化合物P7替换为P89。
实施例17
本实施例与实施例9的区别在于,将化合物P7替换为P103。
对比例1
本对比例与实施例9的区别在于,将化合物P7替换为化合物BCzVBi。
OLED器件发光性能参数的测试
用Keithley 2365A数字纳伏表测试根据实施例以及对比例中制造的显示面板在不同电压下的电流,然后用电流除以发光面积得到显示面板的在不同电压下的电流密度。用Konicaminolta CS-2000分光辐射亮度计测试根据实施例以及对比例制作的显示面板在不同电压下的亮度和辐射能流密度。根据显示面板在不同电压下的电流密度和亮度,得到在相同电流密度下(10mA/cm2)的工作电压Von、电流效率(Cd/A)和外量子效率EQE;通过测量有机发光器件的亮度达到初始亮度的95%时的时间而获得寿命 T95(在500nit测试条件下)结果。测试结果如表2所示。
表2
由表2可知,与采用经典蓝色荧光发光材料BCzVBi作为荧光掺杂剂的对比器件相比,本发明化合物作为蓝光客体材料的器件的电流效率CE 均明显高于对比器件,这主要得益于本发明化合物自身的TADF特性,单线态和三线态之间存在高效的反向系间窜跃的光物理过程,可以利用传统荧光分子(如BCzVBi)跃迁禁阻的三线态激子来发光,从而提高了器件效率。
本发明的化合物由于具有TADF效果,三线态和单线态之间可以形成反向系间穿越的物理过程,可以更高效的同时利用单线态激子和三线态激子。同时本发明化合物具有双极性性质,对空穴和电子均具有良好的传输特性,也可以用作发光层的主体材料,拓宽发光区,提升发光效率和器件的工作寿命。
实施例18
本实施例与实施例9的区别在于,将主体材料mCBP替换为P7,掺杂材料P7替换为红光发光材料Ir(piq)2acac(即,在本实施例中,P7用作主体材料,Ir(piq)2acac用作掺杂材料)。
实施例19
本实施例与实施例9的区别在于,将mCBP替换为P14,化合物P7 替换为绿光发光材料Ir(ppy)3。
实施例20
本实施例与实施例9的区别在于,将mCBP替换为P30,化合物P7 替换为红光发光材料Ir(piq)2acac。
实施例21
本实施例与实施例9的区别在于,将mCBP替换为P39,化合物P7 替换为绿光发光材料Ir(ppy)3。
实施例22
本实施例与实施例9的区别在于,将mCBP替换为P48,化合物P7 替换为绿光发光材料Ir(ppy)3。
实施例23
本实施例与实施例9的区别在于,将mCBP替换为P56,化合物P7 替换为绿光发光材料Ir(ppy)3。
实施例24
本实施例与实施例9的区别在于,将mCBP替换为P86,化合物P7 替换为红光发光材料Ir(piq)2acac。
实施例25
本实施例与实施例9的区别在于,将mCBP替换为P89,化合物P7 替换为绿光发光材料Ir(ppy)3。
实施例26
本实施例与实施例9的区别在于,将mCBP替换为P103,化合物P7 替换为红光发光材料Ir(piq)2acac。
对比实施例2
本实施例与实施例9的区别在于,将化合物P7替换为Ir(ppy)3。
对比实施例3
本对比例与实施例9的区别在于,将化合物P7替换为Ir(piq)2acac。
表3
mCBP经常用作磷光主体材料,Ir(ppy)3是经常使用的绿光磷光材料, Ir(piq)2acac是常用的红光磷光材料。由表3可以看出,与使用mCBP作为磷光主体材料制备的对比器件2和对比器件3相比,采用本发明化合物P7、 P14、P30、P39、P48、P56、P86、P89、P103作为磷光主体材料的有机发光器件(实施例18-实施例26)具有更高的电流效率、更长的器件寿命和更低的工作电压。由此可见,本发明所述的化合物适宜作为绿光和红光的磷光主体材料。
本发明还提供了一种显示装置,其包括如上文所述的有机发光显示面板。在本发明中,有机发光器件可以是OLED,其可以用在有机发光显示装置中,其中有机发光显示装置可以是手机显示屏、电脑显示屏、电视显示屏、智能手表显示屏、智能汽车显示面板、VR或AR头盔显示屏、各种智能设备的显示屏等。图4是根据本发明实施例提供的一种显示装置的示意图。在图4中,20表示手机显示面板,30表示显示装置。
本申请虽然以较佳实施例公开如上,但并不是用来限定权利要求,任何本领域技术人员在不脱离本申请构思的前提下,都可以做出若干可能的变动和修改,因此本申请的保护范围应当以本申请权利要求所界定的范围为准。
Claims (6)
2.根据权利要求1所述的化合物,其特征在于,在化学式1-1、1-2和1-3中,A1和A2相同,D1和D2相同。
4.一种显示面板,包括有机发光器件,其中所述有机发光器件包括相对设置的阳极、阴极,位于阳极与阴极之间的发光层,其中发光层的发光材料包括主体材料和客体材料,所述客体材料为权利要求1至3任一项所述的化合物中的一种或一种以上。
5.一种显示面板,包括有机发光器件,其中所述有机发光器件包括相对设置的阳极、阴极,位于阳极与阴极之间的发光层,其中发光层的发光材料包括主体材料和客体材料,所述主体材料为权利要求1至3任一项所述的化合物中的一种或一种以上。
6.一种显示装置,包括权利要求4或5所述的显示面板。
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