CN109651174B - 有机电致发光化合物、发光材料及有机电致发光器件 - Google Patents
有机电致发光化合物、发光材料及有机电致发光器件 Download PDFInfo
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- CN109651174B CN109651174B CN201910062898.8A CN201910062898A CN109651174B CN 109651174 B CN109651174 B CN 109651174B CN 201910062898 A CN201910062898 A CN 201910062898A CN 109651174 B CN109651174 B CN 109651174B
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- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
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- 238000000862 absorption spectrum Methods 0.000 description 2
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- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
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- 239000002861 polymer material Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 238000006862 quantum yield reaction Methods 0.000 description 1
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- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 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
- 239000010703 silicon Substances 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
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- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- 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
Description
技术领域
本发明涉及有机电致发光化合物、包含该有机电致发光化合物的发光材料以及包含该有机电致发光化合物的有机电致发光器件。
背景技术
自从1987年柯达公司C.W.Tang等人首次报道以真空蒸镀的方法制备出 Alq3为发光材料的双层发光器件以来,有机电致发光器件得到了人们极大的关注。经过30多年的发展,有机电致发光在平板显示、照明方面的引用已经进入产业化初级阶段。
有机电致发光器件一般包括由阳极、金属阴极和它们之间夹着的有机层组成。有机层主要有空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层。有机电致发光器件的基本机制涉及电荷的注入、传输、重组以及形成激子以发光。当外部电压施加到有机电致发光装置时,电子和空穴分别从阴极和阳极注入,电子将从阴极注入到最低未占有分子轨道,而空穴将从阳极注入到最高占有分子轨道中。当电子与空穴在发光层中重组时,形成激子并且随后发光。当发光分子吸收能量达到激发态时,根据电子自旋的统计规则,单线态激子和三重态激子以25%:75%的比例生成。由于三重态激子的衰减是自旋禁阻的,荧光电致发光器件的内部量子效率仅为25%。然而,在含有重金属元素的磷光材料中,其分子内具有较强的自旋-轨道耦合,促进单重态与三重态之间的系间窜越,因而获得来自单重态和三重态两者的发光,磷光电致发光器件的内部量子效率可达100%。
近年来,安达千波矢教授及其同事研发的一种结合热活化型延迟荧光机制的新型荧光有机发光二器件,通过反向系间窜越机制,将自旋禁阻的三重态激子转化为单重态以获得100%的内部量子效率。因此,磷光和延迟荧光电致发光器件的高效率技术受到了广泛的关注。但磷光以及延迟荧光电致发光器件和荧光电致发光器件相比具有寿命短、色纯度差等缺点,尤其是蓝色磷光和延迟荧光电致发光器件中不仅寿命短、色纯度差,发光效率还不够充分,目前还未达到实用化。另外,目前商业化的荧光发光材料有DPVBi、 DSA-ph、二萘蒽等。上述材料由于热稳定差,长时间驱动会引起色纯度降低,导致在面板应用的时候出现色差等问题。因此急需开发一批色纯度、效率、热稳定性方面均能满足要求的新材料。
发明内容
发明要解决的问题
基于上述理由,本发明的目的在于解决现有技术问题并且提供一种具有热稳定性、高发光效率、高亮度以及长寿命的有机电致发光器件。
用于解决问题的方案
本发明提供一种有机电致发光化合物,其由下述式(1)表示:
在所述式(1)中,
M表示C(R1)2或者
其中虚线表示来自M的键;
Z在每次出现时相同或不同,其表示C、CR1或者N;
A表示具有2至5个环的取代或者未取代的稠合芳环单元,Ar1、Ar2在每次出现时相同或者不同地是具有5至30个芳族环原子并且可以被一个或者多个R1取代的芳族或杂芳族环系;
R1在每次出现时相同或不同地是H、D、F、Cl、Br、I、CN、NO2、NR2、 OR2、SR2、C(=O)R2、P(=O)R2、Si(R2)3、具有1至20个碳原子的取代或未取代的直链状或支链状的烷基、具有3至20个碳原子的取代或未取代的环状的烷基、具有2至20个碳原子的烯基或者炔基,或者具有5至40个芳族环原子并且在每种情况下可被一个或多个R2取代的芳族或杂芳族环系;其中所述烷基、烯基或者炔基在每种情况下可被一个或者多个R2取代,并且其中一个或者多个非相邻的CH2基团可被R2C=CR2、C≡C、Si(R2)3、C=O、C=NR2、P(=O)R2、 SO、SO2、NR2、O、S或CONR2代替,并且其中一个或者多个氢原子可以被 D、F、Cl、Br、I、CN或NO2代替;
其中,两个相邻的R1或两个相邻的R2任选地形成单环或多环的脂族、芳族或者杂芳族的环系,所述环系可被一个或者多个R2取代;并且两个或更多个R1可以彼此连接并形成环;
R2在每种情况下相同或不同并且选自H、D、F、CN、具有1至20个碳原子的脂肪族基团、具有5至30个芳族环原子的芳族或杂芳族环系,或具有多环的脂肪族环系,其中一个或多个氢原子可以被D、F、CN取代。
根据本发明所述的有机电致发光化合物,其中所述式(1)中的A具有选自下列式所组成的群组中的一种结构:
其中R2至R15独立地选自由氢原子、具有1至20个碳原子的取代或未取代的烷基、具有6至30个碳原子的取代或未取代的芳基,以及具有3至30个碳原子的取代或未取代的杂芳族基所组成的群组。
根据本发明所述的有机电致发光化合物,其由下述式(1-1)~式(1-4) 中的任一个表示:
其中,Ar1、Ar2、M、Z以及A与式(1)中定义相同。
根据本发明所述的有机电致发光化合物,其中,由所述式(1)表示的化合物选自下述化合物:
本发明还提供一种发光材料,其包含根据本发明所述的有机电致发光化合物。
根据本发明所述的发光材料,其为荧光发光客体材料。
本发明还提供一种有机电致发光器件,其包括:第一电极、与所述第一电极对置而具备的第二电极、以及夹在所述第一电极与所述第二电极之间的至少一个有机层,
其中所述有机层包含根据本发明所述的有机电致发光化合物。
根据本发明所述的有机电致发光器件,其中,包含所述有机电致发光化合物的有机层为发光层。
发明的效果
螺双芴分子具有非平面的空间结构,两个芴单体以sp3杂化的碳原子为中心桥连在一起,得到了正交的三维空间结构,具有优良的热稳定性和成膜性,更重要的是其分子间的空间位阻大,可以有效减少激基缔合物和浓度淬灭等不利因素的产出,因此将其引入到具有电致发光特性的分子中,有利于提高分子的稳定性、色纯度和发光效率等。
本发明的有益效果是,本发明制备的发光材料具有较高的玻璃化转变温度、荧光量子产率、电荷迁移率,可增加有机电致发光器件的效率、寿命以及降低驱动电压和功率消耗。本发明的式(1)化合物作为有机电致发光器件的发光材料(掺杂化合物),可以使得薄膜状态稳定,耐热性优异。通过使用该化合物,能够制得高效率、高亮度、长寿命、低驱动电压的有机电致发光器件。
附图说明
图1为实施例中OLED3中的发光材料化合物83的紫外吸收光谱 (UV-Vis)和室温荧光光谱(PL);紫外吸收光谱和室温荧光光谱在二氯甲烷的稀溶液(1×10-5mol/L)中测得。
图2为实施例中OLED2和OLED3的有机电致发光光谱。
图3是显示实施例和比较例的有机电致发光器件的构造的图。
附图标记说明
1 基板
2 阳极
3 空穴注入层
4 空穴传输层I
5 空穴传输层II
6 电子阻挡层
7 发光层
8 空穴阻挡层
9 电子传输层
10 电子注入层
11 阴极
具体实施方式
以下,对本发明的实施方式进行详细说明。但是,本发明不受以下实施方式的限定。
本发明的有机电致发光化合物由下述式(1)表示:
在所述式(1)中,
M表示C(R1)2或者
其中虚线表示来自M的键;
Z在每次出现时相同或不同,其表示C、CR1或者N;
A表示具有2至5个环的取代或者未取代的稠合芳环单元,Ar1、Ar2在每次出现时相同或者不同地是具有5至30个芳族环原子并且可以被一个或者多个R1取代的芳族或杂芳族环系;
R1在每次出现时相同或不同地是H、D、F、Cl、Br、I、CN、NO2、NR2、 OR2、SR2、C(=O)R2、P(=O)R2、Si(R2)3、具有1至20个碳原子的取代或未取代的直链状或支链状的烷基、具有3至20个碳原子的取代或未取代的环状的烷基、具有2至20个碳原子的烯基或者炔基,或者具有5至40个芳族环原子并且在每种情况下可被一个或多个R2取代的芳族或杂芳族环系;其中所述烷基、烯基或者炔基在每种情况下可被一个或者多个R2取代,并且其中一个或者多个非相邻的CH2基团可被R2C=CR2、C≡C、Si(R2)3、C=O、C=NR2、P(=O)R2、 SO、SO2、NR2、O、S或CONR2代替,并且其中一个或者多个氢原子可以被 D、F、Cl、Br、I、CN或NO2代替;
其中,两个相邻的R1或两个相邻的R2任选地形成单环或多环的脂族、芳族或者杂芳族的环系,所述环系可被一个或者多个R2取代;并且两个或更多个R1可以彼此连接并形成环;
R2在每种情况下相同或不同并且选自H、D、F、CN、具有1至20个碳原子的脂肪族基团、具有5至30个芳族环原子的芳族或杂芳族环系,或具有多环的脂肪族环系,其中一个或多个氢原子可以被D、F、CN取代。
作为式(1)中具有2至5个环的稠合芳环单元的例子,具体而言,可列举出联苯、三联苯、四联苯、萘、蒽、苊烯、芴、菲、茚、芘、苝、荧蒽、苯并蒽、苯并菲等。
作为稠合芳环单元上的取代基,可以例示如下:
氘原子,
氰基,
硝基,
卤素原子,例如氟原子、氯原子、溴原子或碘原子;
具有1至6个碳原子的烷基,例如,甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基或正己基;
具有1至6个碳原子的烷氧基,例如甲氧基、乙氧基或丙氧基;
烯基,例如乙烯基或烯丙基;
芳氧基,例如苯氧基或甲苯氧基;
芳基烷氧基,例如苄氧基或苯乙氧基;
芳族烃基或稠合多环芳族基,例如苯基、联苯基、三联苯基、萘基、蒽基、菲基、芴基、茚基、芘基、苝基、荧蒽基、苯并[9,10]菲基或螺二芴基;
芳族杂环基,例如吡啶基、噻吩基、呋喃基、吡咯基、喹啉基、异喹啉基、苯并呋喃基、苯并噻吩基、吲哚基、咔唑基、苯并噁唑基、苯并噻唑基、喹喔啉基、苯并咪唑基、吡唑基、二苯并呋喃基、二苯并噻吩基、氮杂芴基、二氮杂芴基、咔啉基、氮杂螺二芴基或二氮杂螺二芴基;
芳基乙烯基,例如苯乙烯基或萘乙烯基;和
酰基,例如乙酰基或苯甲酰基。
由Ar1、Ar2表示的芳族环系可以例示出苯、联苯、三联苯、四联苯、苯乙烯、萘、蒽、苊、菲、芴、茚、芘、苝、荧蒽、苯并[9,10]菲、螺二芴等。
由Ar1、Ar2表示的杂芳族环系可以例示出吡啶、联吡啶、三联吡啶、嘧啶、吡嗪、哒嗪、三嗪、吡咯、吡唑、咪唑、三唑、噁唑、异噁唑、噻唑、异噻唑、噁二唑、噻二唑、呋喃、噻吩、喹啉、异喹啉、喹喔啉、喹唑啉、萘啶、吲哚、异吲哚、苯并咪唑、苯并三唑、苯并呋喃、苯并噻吩、苯并噁唑、苯并噁二唑、苯并噻唑、苯并噻二唑、吡啶并吡咯、吡啶并咪唑、吡啶并三唑、蝶啶、吖啶、吩嗪、菲咯啉、吩噁嗪、吩噻嗪、吩硒嗪、吩碲嗪、吩磷嗪、咔唑、咔啉、二苯并呋喃、二苯并噻吩、呫吨等。
作为式(1)的R1中具有1至20个碳原子的直链状或支链状的烷基,可以例示出甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基、异己基、正庚基、异庚基、正辛基、异辛基、正壬基、异壬基、正癸基、异癸基、正十一烷基、异十一烷基、正十二烷基、异十二烷基、正十三烷基、异十三烷基、正十四烷基、异十四烷基、正十五烷基、异十五烷基、正十六烷基、异十六烷基、正十七烷基、异十七烷基、正十八烷基、异十八烷基、正十九烷基、异十九烷基、正二十烷基、异二十烷基等。
作为式(1)的R1中具有3至20个碳原子的环状的烷基,可以例示出环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环癸基、环十一烷基、环十二烷基、环十三烷基、环十四烷基、环十五烷基、环十六烷基、环十七烷基、环十八烷基、环十九烷基、环二十烷基、1-金刚烷基、2-金刚烷基等。
作为式(1)的R1中具有2至20个碳原子的烯基或者炔基,可以例示出乙烯基、烯丙基、异丙烯基、2-丁烯基、1-戊烯基、2-己烯基、1-庚烯基、 1-辛烯基、1-壬烯基、1-癸烯基、1-十一烯基、1-十二烯基、1-十三烯基、1- 十四烯基、1-十五烯基、1-十六烯基、1-十七烯基、1-十八烯基、1-十九烯基、 1-二十烯基、2-庚烯基、2-甲基-2-己烯基、2-辛烯基、2-乙基己烯基、3-甲基 -2-庚烯基、2-壬烯基、2-癸烯基、2-十六烯基、2-十八烯基;乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基、辛炔基、壬炔基、癸炔基、1-十一炔基、1-十二炔基、1-十三炔基、1-十四炔基、1-十五炔基、1-十六炔基、1- 十七炔基、1-十八炔基、1-十九炔基、1-二十炔基等。
作为式(1)的R1中具有5至40个芳族环原子的芳族或杂芳族环系,可以例示出与上述由Ar1、Ar2表示的芳族或杂芳族环系相同的例子。
作为式(1)的R1中的取代基,可以例示出与上述稠合芳环单元上的取代基相同的例子。
作为式(1)的R2中的具有1至20个碳原子的脂肪族基团、具有5至 30个芳族环原子的芳族或杂芳族环系,可以例示出与上述R1中相同的例子。
作为式(1)的R2中的具有多环的脂肪族环系,可以例示出脂环族环氧化合物等。
作为式(1)的R2中的取代基,可以例示出与上述R1中的取代基相同的例子。
优选地,所述式(1)中的A具有选自下列式所组成的群组中的一种结构:
其中R2至R15独立地选自由氢原子、具有1至20个碳原子的取代或未取代的烷基、具有6至30个碳原子的取代或未取代的芳基,以及具有3至30个碳原子的取代或未取代的杂芳族基所组成的群组。
作为这里的烷基、芳基和杂芳族基,可以例示出与上述Ar1、Ar2、R1、 R2中相同的例子。
优选地,本发明的有机电致发光化合物由下述式(1-1)~式(1-4)中的任一个表示:
其中,Ar1、Ar2、M、Z以及A与式(1)中定义相同。
优选地,本发明的有机电致发光化合物选自下述化合物,但本发明不限于这些化合物。
本发明的有机电致发光化合物的纯化通过利用柱色谱的纯化、利用硅胶、活性炭、活性白土等的吸附纯化、利用溶剂的重结晶、析晶法、升华纯化法等来进行。有机电致发光化合物的鉴定利用质谱、元素分析进行。
<发光材料>
本发明的发光材料包含上述有机电致发光化合物。
本发明的发光材料可用于有机电致发光器件中,尤其作为有机电致发光器件的荧光发光客体材料。
<有机电致发光器件>
本发明的有机电致发光器件包括:第一电极、与第一电极对置而具备的第二电极、以及夹在第一电极与第二电极之间的至少一个有机层,其中有机层包含本发明的有机电致发光化合物。
图3是显示本发明的有机电致发光器件的构造的图。如图3所示,在本发明的有机电致发光器件中,例如,阳极2、空穴注入层3、空穴传输层Ⅰ4、空穴传输层Ⅱ5、电子阻挡层6、发光层7、空穴阻挡层8、电子传输层9、电子注入层10和阴极11依次设置在基板1上。
本发明的有机电致发光器件不限于这样的结构,例如在该多层结构中,可以省略一些有机层。例如,可以是阳极2与空穴传输层Ⅰ4之间的空穴注入层3、发光层7与电子传输层9之间的空穴阻挡层8、以及电子传输层9与阴极 11之间的电子注入层10被省略,并且在基板1上依次设置阳极2、空穴传输层Ⅰ4、发光层7、电子传输层9和阴极11的构型。
根据本发明的有机电致发光器件除了上述有机层包含由上述式(1)表示的化合物以外,可以通过本技术领域公知的材料和方法进行制造。另外,在上述有机电致发光器件包含多个有机层的情况下,上述有机层可以由相同的物质或不同的物质形成。
例如,根据本发明的有机电致发光器件可以通过在基板上依次层叠第一电极、有机层和第二电极而制造。此时,可以如下制造:利用溅射法或电子束蒸发法之类的PVD(物理蒸镀法)方法,在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成阳极,然后在该阳极上形成包含空穴注入层、空穴传输层、发光层和电子传输层的有机层,之后在该有机物层上蒸镀可用作阴极的物质。但是,制造方法并不限定于此。
作为一个例子,上述第一电极为阳极,上述第二电极为阴极,或者上述第一电极为阴极,上述第二电极为阳极。
作为本发明的有机电致发光器件的阳极,可以由公知的电极材料构成。例如使用具有大的功函数的电极材料,如钒、铬、铜、锌、金等金属或它们的合金;如氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;如ZnO:Al或SNO2:Sb等金属与氧化物的组合;聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺等导电性高分子等。这些之中,优选ITO。
作为本发明的有机电致发光器件的空穴注入层,可以使用公知的具有空穴注入性质的材料。例如可列举:以铜酞菁为代表的卟啉化合物、萘二胺衍生物、星型的三苯胺衍生物、分子中具有3个以上三苯胺结构通过单键或不含杂原子的二价基团连接的结构的芳胺化合物等三苯胺三聚体及四聚体、六氰基氮杂苯并菲等受体型杂环化合物、涂布型高分子材料。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
作为本发明的有机电致发光器件的空穴传输层I和II,可以使用公知的具有空穴传输性的材料。例如可列举:含有间咔唑基苯基的化合物;如N,N’- 二苯基-N,N’-二(间甲苯基)联苯胺(TPD)、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯 -4,4'-二胺(NPB)、N,N,N’,N’-四联苯基联苯胺等联苯胺衍生物;1,1-双[(二-4- 甲苯基氨基)苯基]环己烷(TAPC);各种三苯胺三聚体及四聚体;9,9',9”-三苯基-9H,9'H,9”H-3,3':6',3”-三咔唑(Tris-PCz)等。它们可以单独地成膜,也可以以与其它材料一起混合成膜而成的单层的形式来使用,还可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或者单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
此外,空穴注入层或空穴传输层中,也可以使用对于该层中通常使用的材料进一步P掺杂三溴苯胺六氯化锑、轴烯衍生物等而成的物质、其部分结构中具有TPD等联苯胺衍生物的结构的高分子化合物等。
作为本发明的有机电致发光器件的电子阻挡层,可以使用具有电子阻挡作用的公知化合物形成。例如,可列举出:3,3'-二(N-咔唑基)-1,1'-联苯(mCBP)、 4,4’,4”-三(N-咔唑基)三苯胺(TCTA)、9,9-双[4-(咔唑-9-基)苯基]芴、1,3-双(咔唑-9-基)苯(mCP)、2,2-双(4-咔唑-9-基苯基)金刚烷(Ad-Cz)等咔唑衍生物; 9-[4-(咔唑-9-基)苯基]-9-[4-(三苯基甲硅烷基)苯基]-9H-芴所代表的具有三苯基甲硅烷基和三芳胺结构的化合物;电子阻挡性高的单胺化合物、各种三苯胺二聚体等具备电子阻挡作用的化合物。它们可以单独地成膜,也可以与其它材料一起混合成膜而成的单层的形式来使用,还可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或者单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
作为本发明的有机电致发光器件的发光层,优选使用包含式(1)所示的有机电致发光化合物的发光材料。除此之外,还可以使用以Alq3为首的羟基喹啉衍生物的金属络合物等各种金属络合物、具有嘧啶环结构的化合物、蒽衍生物、双苯乙烯基苯衍生物、芘衍生物、噁唑衍生物、聚对亚苯基亚乙烯基衍生物等。
发光层可以由主体材料和掺杂材料构成。作为主体材料,例如可以使用 mCBP、mCP、噻唑衍生物、苯并咪唑衍生物、聚二烷基芴衍生物、具有吲哚环作为稠合环的部分结构的杂环化合物等。
作为掺杂材料,优选使用包含式(1)所示的有机电致发光化合物的发光材料。本发明的有机电致发光化合物的掺杂重量比例优选为0.1~50%,更优选为0.5~20%,特别优选为0.5~8%。
掺杂材料除了使用本发明的有机电致发光化合物之外,还可以使用芘衍生物、蒽衍生物、喹吖啶酮、香豆素、红荧烯、苝和它们的衍生物、苯并吡喃衍生物、罗丹明衍生物、氨基苯乙烯基衍生物、螺环双芴衍生物等。它们可以单独地成膜,也可以与其它材料一起混合成膜而成的单层的形式来使用,还可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或者单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
作为本发明的有机电致发光器件的空穴阻挡层,可以使用公知的具有空穴阻挡性的化合物来形成。例如可以使用2,4,6-三(3-苯基)-1,3,5-三嗪(T2T)、 1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯(TPBi)、浴铜灵(BCP)等菲咯啉衍生物、铝(III)双(2-甲基-8-羟基喹啉)-4-苯基苯酚盐(BAlq)等喹啉醇衍生物的金属络合物、以及各种稀土类络合物、噁唑衍生物、三唑衍生物、三嗪衍生物等具有空穴阻挡作用的化合物。它们可以单独地成膜,也可以以与其它材料一起混合成膜而成的单层的形式来使用,也可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
上述具有空穴阻挡性的材料也可以用于下述的电子传输层的形成。即,通过使用上述公知的具有空穴阻挡性的材料,可以形成同时作为空穴阻挡层和电子传输层的层。
作为本发明的有机电致发光器件的电子传输层,使用公知的具有电子传输性的化合物形成。例如可以使用Alq3、BAlq为首的羟基喹啉衍生物的金属络合物;各种金属络合物;三唑衍生物;三嗪衍生物;噁二唑衍生物;吡啶衍生物;双(10-羟基苯并[H]喹啉)铍(Be(bq2));如2-[4-(9,10-二萘-2-蒽-2-基) 苯基]-1-苯基-1H-苯并咪唑(ZADN)等苯并咪唑衍生物;噻二唑衍生物;蒽衍生物;碳二亚胺衍生物;喹喔啉衍生物;吡啶并吲哚衍生物;菲咯啉衍生物;噻咯衍生物等。它们可以单独地成膜,也可以以与其它材料一起混合成膜而成的单层的形式来使用,也可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
作为本发明的有机电致发光器件的电子注入层,可以使用本身公知的材料形成。例如可以使用氟化锂、氟化铯等碱金属盐;氟化镁等碱土金属盐;羟基喹啉锂等羟基喹啉衍生物的金属络合物;氧化铝等金属氧化物等。
在电子注入层或电子传输层中,对于该层中通常使用的材料,可以使用进而N掺杂铯等金属、三芳基氧化膦衍生物等而成的材料。
作为本发明的有机电致发光器件的阴极,优选使用具有低功函数的电极材料如铝、镁,或者具有低功函数的合金如镁银合金、镁铟合金、铝镁合金作为电极材料。
作为本发明的基板,可以使用传统的有机发光器件中的基板,例如玻璃或塑料。在本发明中,选用玻璃基板。
实施例
在以下实施例中对由上述式(1)表示的化合物及包含其的有机电致发光器件的制造进行具体说明。但是,下述实施例仅用于对本发明进行例示,本发明的范围不限于此。
制备例1:
本制备例用于制备化合物44,其结构式及合成路线如下所示:
中间体44A的合成
在250mL Schlenk瓶中,加入4-溴-9,9'-螺双芴10.19g(25.77mmol),苯胺3.00g(15.00mmol),醋酸钯0.36g(1.6mmol),三叔丁基膦四氟硼酸盐 0.93g(3.22mmol),叔丁醇钠9.29g(96.64mmol),甲苯150mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用100mL二氯甲烷和50mL水溶解残留物,水洗,分出有机层,水层用30mL二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=3:1(V/V)),蒸去溶剂,干燥后,得到9.70g白色固体,收率为73.9%。MS(EI):m/z407.541[M+].Anal.calcd for C31H21N(%):C, 91.37;H,5.19;N,3.44;found:C,91.26;H,5.27;N,3.47。
化合物44的合成
在250mL Schlenk瓶中,加入中间体44A 5.00g(12.27mmol),9,10-二溴蒽1.65g(4.91mmol),三(二亚苄基丙酮)二钯0.22g(0.25mmol),三叔丁基膦四氟硼酸盐0.14g(0.49mmol),叔丁醇钠2.36g(24.54mmol),甲苯 150mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用 200mL二氯甲烷和50mL水溶解残留物,水洗,分出有机层,水层用15mL 二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=2.5:1(V/V)),蒸去溶剂,干燥后,得到3.20g白色结晶,收率为65.9%。MS(EI):m/z 988.47[M+].Anal.calcd for C76H48N2(%):C,92.28;H,4.89;N,2.83;found:C,92.15;H,4.87;N,2.98。
制备例2:
本制备例用于制备化合物74,其结构式及合成路线如下所示:
中间体74A的合成
在250mL Schlenk瓶中,加入9,9-二甲基-2-溴芴7.04g(25.77mmol),苯胺3.00g(32.21mmol),醋酸钯0.36g(1.61mmol),三叔丁基膦四氟硼酸盐0.93g(3.22mmol),叔丁醇钠9.29g(96.64mmol),甲苯150mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用150mL二氯甲烷和100mL水溶解残留物,水洗,分出有机层,水层用15mL二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=4:1(V/V)),蒸去溶剂,干燥后,得到6.20g白色结晶,收率为67.44%。MS(EI):m/z285.34[M+].Anal.calcd for C21H19N(%): C,88.38;H,6.71;N,4.91;found:C,88.35;H,6.68;N,4.97。
化合物74的合成
在250mL Schlenk瓶中,加入中间体74A 5.00g(17.52mmol),1,6-二异丙基-3,8-二溴芘3.11g(7.01mmol),三(二亚苄基丙酮)二钯0.32g(0.35 mmol),三叔丁基膦四氟硼酸盐0.20g(0.70mmol),叔丁醇钠3.37g(35.04 mmol),甲苯150mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用150mL二氯甲烷和50mL水溶解残留物,水洗,分出有机层,水层用15mL二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=3:1(V/V)),蒸去溶剂,干燥后,得到3.60g白色结晶,收率为60.2%。MS(EI):m/z 852.68[M+].Anal. calcd for C64H56N2(%):C,90.10;H,6.62;N,3.28;found:C,90.24;H,6.57;N, 3.19。
制备例3:
本制备例用于制备化合物83,其结构式及合成路线如下所示:
中间体83A的合成
在250mL Schlenk瓶中,加入3-溴-9,9'-螺双芴5.90g(14.93mmol),苯胺2.00g(18.66mmol),醋酸钯0.21g(0.09mmol),三叔丁基膦四氟硼酸盐0.54g(1.87mmol),叔丁醇钠5.38g(56.0mmol),甲苯120mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用200mL二氯甲烷和 50mL水溶解残留物,水洗,分出有机层,水层用15mL二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=2:1(V/V)),蒸去溶剂,干燥后,得到6.40g白色结晶,收率为81.3%。MS(EI):m/z407.61[M+].Anal.calcd for C31H21N(%):C,91.37; H,5.19;N,3.44;found:C,91.31,H,5.23;N,3.46。
化合物83的合成
在250mL Schlenk瓶中,加入中间体83A 2.00g(4.74mmol),1,6-二异丙基-3,8-二溴芘1.00g(2.06mmol),三(二亚苄基丙酮)二钯0.09g(0.1mmol),三叔丁基膦四氟硼酸盐0.06g(0.2mmol),叔丁醇钠0.99g(10.31mmol),甲苯100mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用100mL二氯甲烷和50mL水溶解残留物,水洗,分出有机层,水层用15mL 二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=3:1(V/V)),蒸去溶剂,干燥后,得到1.55g白色结晶,收率为66.76%。MS(EI):m/z 1096.75[M+].Anal.calcd for C84H60N2(%):C,91.94;H,5.51;N,2.55;found:C,91.86;H,5.57;N,2.57。
制备例4:
本制备例用于制备化合物87,其结构式及合成路线如下所示:
中间体87A的合成
在250mL Schlenk瓶中,加入3-溴-9,9'-螺双芴4.68g(11.83mmol),4- 异丙基苯胺2.00g(14.79mmol),醋酸钯0.17g(0.74mmol),三叔丁基膦四氟硼酸盐0.43g(1.48mmol),叔丁醇钠4.26g(44.38mmol),甲苯120mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用100mL二氯甲烷和50mL水溶解残留物,水洗,分出有机层,水层用15mL二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=2:1(V/V)),蒸去溶剂,干燥后,得到5.65g白色结晶,收率为85%。MS(EI):m/z449.71[M+].Anal.calcd for C34H27N(%): C,90.83;H,6.05;N,3.12;found:C,90.73;H,6.13;N,3.14。
化合物87的合成
在250mL Schlenk瓶中,加入中间体87A 5.00g(11.12mmol),1,6-二异丙基-3,8-二溴芘1.98g(4.45mmol),三(二亚苄基丙酮)二钯0.20g(0.22mmol),三叔丁基膦四氟硼酸盐0.13g(0.44mmol),叔丁醇钠2.14g(22.24mmol),甲苯150mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用150mL二氯甲烷和50mL水溶解残留物,水洗,分出有机层,水层用15 mL二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=3:1(V/V)),蒸去溶剂,干燥后,得到3.30g白色结晶,收率为62.8%。MS(EI):m/z 1180.54[M+].Anal.calcd for C90H72N2(%):C,91.49;H,6.14;N,2.37;found:C,91.34;H,6.37;N,2.29。
制备例5:
本制备例用于制备化合物98,其结构式及合成路线如下所示:
化合物98的合成
在250mL Schlenk瓶中,加入中间体74A6.00g(21.02mmol),6,12-二溴屈3.25g(8.41mmol),三(二亚苄基丙酮)二钯0.38g(0.42mmol),三叔丁基膦四氟硼酸盐0.24g(0.84mmol),叔丁醇钠4.04g(42.05mmol),甲苯 150mL,在氩气保护下,回流搅拌反应12小时,反应完毕。蒸去溶剂,用 150mL二氯甲烷和50mL水溶解残留物,水洗,分出有机层,水层用15mL 二氯甲烷萃取两次,合并有机层,蒸去溶剂后,残留物经柱层析分离(硅胶为350目,淋洗液为石油醚:二氯甲烷=3:1(V/V)),蒸去溶剂,干燥后,得到3.60g白色结晶,收率为60.2%。MS(EI):m/z 794.87[M+].Anal.calcd for C60H46N2(%):C,90.64;H,5.83;N,3.52;found:C,90.62;H,6.87;N,2.51。
下面是本发明化合物的应用实施例
实施例
将空穴注入层3、空穴传输层I 4、空穴传输层II 5、电子阻挡层6、发光层7、空穴阻挡层8、电子传输层9、电子注入层10和阴极11依次形成在预先形成为玻璃基板1上的透明阳极2上,以制备如图3所示的有机电致发光器件。
具体地,将涂布了厚度为100nm的ITO透明导电层的玻璃基板在Decon 90碱性清洗液中超声处理,去离子水中冲洗,在丙酮和乙醇中各清洗三次,在洁净的环境下烘烤至完全除去水分,用紫外光和臭氧清洗,并用低能阳离子束轰击表面。将该带有ITO电极的玻璃基板置入真空腔内,抽真空至 4×10-5~2×10-5Pa。
然后在上述带有ITO电极的玻璃基板上以0.2nm/s的蒸镀速率蒸镀 2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(HAT-CN)以形成膜厚为10 nm的层作为空穴注入层(HIL),在空穴注入层上,以2.0nm/s的蒸镀速率蒸镀N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB)以形成膜厚为40nm 的层作为空穴传输层I(HTL I),然后在空穴传输层I(HTL I)上,以2.0nm/s 的蒸镀速率蒸镀9,9',9”-三苯基-9H,9'H,9”H-3,3':6',3”-三咔唑(Tris-PCz)以形成膜厚为20nm的层作为空穴传输层II(HTL II)。在空穴传输层II上,以2.0 nm/s的蒸镀速率蒸镀3,3'-二(N-咔唑基)-1,1'-联苯(mCBP)以形成膜厚为15nm 的层作为电子阻挡层(EBL),在电子阻挡层上,以9-(4-(1-萘基)-10-(2-萘基) 蒽(NNPA)的蒸镀速率为2.0nm/s与制备例1、2、3、4、5的化合物(化合物 44、74、83、87和98)的蒸镀速率为0.16nm/s的蒸镀速率进行双源共蒸,形成膜厚为20nm的层作为发光层,制备例1、2、3、4和5的化合物(化合物 44、74、83、87和98)的掺杂质量比例为8wt%。在发光层上,以2.0nm/s 的蒸镀速率蒸镀2,4,6-三(3-苯基)-1,3,5-三嗪(T2T)以形成膜厚为10nm的层作为空穴阻挡层(HBL)。在空穴阻挡层上,以2.0nm/s的蒸镀速率蒸镀 2-[4-(9,10-二萘-2-蒽-2-基)苯基]-1-苯基-1H-苯并咪唑(ZADN)以形成膜厚为 40nm的层作为电子传输层(ETL)。在电子传输层上,以0.2nm/s的蒸镀速率蒸镀8-羟基喹啉-锂(Liq)以形成膜厚为2nm的层作为电子注入层。最后,以 3.0nm/s以上的蒸镀速率蒸镀铝,形成膜厚为100nm的阴极。
器件性能测试:器件的电流-亮度-电压特性是由带有校正过的硅光电二极管的Keithley源测量系(Keithley 2400Sourcemeter、Keithley 2000 Currentmeter)完成的,电致发光光谱是由Photo research公司PR655光谱仪测量的,器件的外部量子效率通过文献Adv.Mater.,2003,15,1043–1048的方法计算可得。器件寿命是指以10000坎特拉每平方米为起始亮度,衰减到 9000坎特拉每平方米(90%)的时间。所有器件均在氮气环境中封装。
实施例涉及的化合物结构如下:
实施例制备的有机电致发光器件(OLED1-5)的结构和各层的膜厚厚度如下:
OLED1:
ITO/HAT-CN(10nm)/NPB(40nm)/
mCBP(15nm)/NNPA:44(20nm,8wt%)/T2T(10nm)/ZADN(40nm)/Liq(2nm)/ Al(100nm)
OLED2:
ITO/HAT-CN(10nm)/NPB(40nm)/
mCBP(15nm)/NNPA:74(20nm,8wt%)/T2T(10nm)/ZADN(40nm)/Liq(2nm)/ Al(100nm)
OLED3:
ITO/HAT-CN(10nm)/NPB(40nm)/
mCBP(15nm)/NNPA:83(20nm,8wt%)/T2T(10nm)/ZADN(40nm)/Liq(2nm)/ Al(100nm)
OLED4:
ITO/HAT-CN(10nm)/NPB(40nm)/
mCBP(15nm)/NNPA:87(20nm,8wt%)/T2T(10nm)/ZADN(40nm)/Liq(2nm)/ Al(100nm)
OLED5:
ITO/HAT-CN(10nm)/NPB(40nm)/
mCBP(15nm)/NNPA:98(20nm,8wt%)/T2T(10nm)/ZADN(40nm)/Liq(2nm)/ Al(100nm)
比较例
比较例1和2的制备方法与实施例相同,仅是改变荧光发光化合物。
比较例1的器件结构如下:
ITO/HAT-CN(10nm)/NPB(40nm)/mCBP(15nm)/NNPA:DPAVBi(20nm, 8wt%)/T2T(10nm)/ZADN(40nm)/Liq(2nm)/Al(100nm)
比较例2的器件结构如下:
ITO/HAT-CN(10nm)/NPB(40nm)/mCBP(15nm)/NNPA:C545T(20nm,5 wt%)/T2T(10nm)/ZADN(40nm)/Liq(2nm)/Al(100nm)
实施例和比较例的器件的性能数据见下表1。
表1器件性能数据
由表1可见,与比较例1和2相比,用本发明荧光发光材料制备的绿色和蓝色有机电致发光器件的发光效率和器件寿命明显提高。另外,蓝色有机电致发光器件的色纯度明显好于采用现有技术中的天蓝色材料DPAVBi所制备的有机电致发光器件。
产业上的可利用性
本发明的有机电致发光化合物具有极好的发光效率,优异的材料色纯度和寿命特性。因此,由该化合物可以制备具有极佳使用寿命的有机电致发光器件。
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