CN113793905A - 具有高效率的荧光有机发光元件 - Google Patents
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- CN113793905A CN113793905A CN202111113056.4A CN202111113056A CN113793905A CN 113793905 A CN113793905 A CN 113793905A CN 202111113056 A CN202111113056 A CN 202111113056A CN 113793905 A CN113793905 A CN 113793905A
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- 230000003111 delayed effect Effects 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims description 135
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- 239000001257 hydrogen Substances 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 24
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- 125000003118 aryl group Chemical group 0.000 claims description 18
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- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 10
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- 229920001577 copolymer Polymers 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 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
- ZDAWFMCVTXSZTC-UHFFFAOYSA-N 2-n',7-n'-dinaphthalen-1-yl-2-n',7-n'-diphenyl-9,9'-spirobi[fluorene]-2',7'-diamine 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)C23C4=CC=CC=C4C4=CC=CC=C43)C2=C1 ZDAWFMCVTXSZTC-UHFFFAOYSA-N 0.000 description 2
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- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
- CUQGKGMUSQKHFO-UHFFFAOYSA-N 9-(6-carbazol-9-ylpyridin-2-yl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=N1 CUQGKGMUSQKHFO-UHFFFAOYSA-N 0.000 description 2
- FWXNJWAXBVMBGL-UHFFFAOYSA-N 9-n,9-n,10-n,10-n-tetrakis(4-methylphenyl)anthracene-9,10-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C2=CC=CC=C2C(N(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)=C2C=CC=CC2=1)C1=CC=C(C)C=C1 FWXNJWAXBVMBGL-UHFFFAOYSA-N 0.000 description 2
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
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- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
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- MBRXYYRVMRQLKQ-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetrakis(3-methylphenyl)benzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 MBRXYYRVMRQLKQ-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 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
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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Abstract
本申请涉及具有高效率的荧光有机发光元件。本发明涉及一种发射延迟荧光的有机发光元件,其在发光层中包含特定经取代的1,2,4‑三唑衍生物、1,2,4‑噁二唑衍生物或1,2,4‑噻二唑衍生物;包含所述特定经取代的1,2,4‑三唑衍生物、1,2,4‑噁二唑衍生物或1,2,4‑噻二唑衍生物的发光层;特定的特定经取代的1,2,4‑三唑衍生物、1,2,4‑噁二唑衍生物和1,2,4‑噻二唑衍生物;和包含所述特定1,2,4‑唑衍生物的有机发光元件以及包含所述特定1,2,4‑唑衍生物的发光层。
Description
本申请为申请日2015年09月25日,申请号201580048432.2,名称为“具有高效率的荧光有机发光元件”的发明专利申请的分案申请。
技术领域
本发明涉及一种发射延迟荧光的有机发光元件,其在发光层中包含特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物或1,2,4-噻二唑衍生物;包含所述特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物或1,2,4-噻二唑衍生物的发光层;特定的特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物和1,2,4-噻二唑衍生物;和包含所述特定1,2,4-唑衍生物的有机发光元件以及包含所述特定1,2,4-唑衍生物的发光层;所述特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物和1,2,4-噻二唑衍生物用于电子照相感光器、光电转换器、传感器、染料激光器、太阳能电池装置和有机发光元件的用途,和所述特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物和1,2,4-噻二唑衍生物用于产生延迟荧光发射的用途。
背景技术
特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物和1,2,4-噻二唑衍生物展现TADF(热激活延迟荧光)特征,通常在298K下。
TADF为涉及三重态(T1)向上转换为单重态(S1)激发态的有效三重态收集方法。
展现TADF特征的衍生物的特征在于在S1与T1之间具有足够小的能隙(ΔEST)以实现T1到S1的三重态激子的向上转换。
本发明因此涉及发射延迟荧光的有机发光元件,其包含特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物和1,24-噻二唑衍生物作为热激活延迟荧光(TADF)发射体(客体)和/或主体。所述有机发光元件展示高电致发光效率。
OLED发光材料的发展为重要问题且这些材料已分类成两个主要类别。第一类别涉及荧光材料,其仅可收获通过电激励产生的单重态激子(25%)。第二类别涉及磷光材料,其可收获产生的三重态激子(75%)。单重态和三重态激子的分支比为1:3。因此,在近来的装置中,磷光材料和其相关技术已对于获得高EL效率来说必不可少。但是,磷光材料一般基于含有Ir或Pt的有机金属化合物。这些金属相当昂贵且依赖于有限的全球资源。
最近,C.阿达奇(C.Adachi)等人在先进材料(Adv.Mater.),2009,21,4802;应用物理学报(Appl.Phys.Lett.),2011,98,083302和化学通讯(Chem.Commun.),2012,48,9580中描述作为第三代发光材料代替常规荧光和磷光物质的热激活延迟荧光(thermallyactivated delayed fluorescence,TADF)的替代概念。
TADF强烈依赖于单个分子中的HOMO-LUMO分离。TADF材料在S1与T1之间具有足够小的能隙(ΔEST)以使三重态激子能自T1向上转换为S1。此小ΔEST使TADF材料能够实现在S1下通过电激励产生的100%激子形成。
ΔEST为分子的最低激发单重态S1与最低激发三重态T1之间的差异。在S1与T1之间的能隙(ΔEST)足够小以提供自T1至S1的三重态激子的热向上转换(根据波耳兹曼分布(Boltzmann distribution)或依据热能kBT)的情况下,允许自S1状态的热活化光发射(TADF),其基于以下方程式:
Int(S1→S0)/Int(T1→T0)=k(S1)/k(T1)exp(-ΔE/kBT)
其中
Int(S1→S0)/Int(T1→T0)为自S1状态和T1状态的发射的强度比
kB为玻尔兹曼常数(Boltzmann constant)
T为绝对温度
k(S1)/k(T1)为自电子基态S0中的单重态S1状态和三重态T1状态的跃迁过程的率比。
WO 2006/114377 A1涉及包含含有式(I)或(II)的三唑化合物的有机层的电致发光装置:
三唑化合物为有机电致发光层的适合组分,根据实例作为主体组分。根据实例,以下三唑化合物用作OLED中的主体材料:
US 2010/0243959 A1涉及式G1的衍生物
化合物用作对于发光元件中的磷光以及荧光发射体具有双极特性的主体。化合物G1的实例为:
US 2010/0240902 A1涉及式1的噁二唑衍生物
化合物用于发光元件中的发光层中。化合物1的实例为:
Q.李(Li)等人,染料和颜料(Dyes and Pigments)101(2014)142-148涉及用于蓝色磷光OLED的基于1,2,4-噁二唑的新双极主体材料的合成。提及以下主体材料:
J.吉恩(Jin)等人,材料化学(Chem.Mater.)2014(26)2388-2395涉及用于磷光有机发光二极管的基于1,2,4-噻二唑的双极主体材料。提及以下主体材料:
CN 10358870 A涉及3,5-二苯基取代的1,2,4-噻二唑衍生物的设计和合成以及3,5-二苯基取代的1,2,4-噻二唑衍生物在有机电致发光装置(OLED)中的应用。3,5-二苯基取代的1,2,4-噻二唑衍生物可在OLED的发光层中用作主体或发光材料或在OLED的传输层中用作空穴或电子传输材料。根据CN 10358870 A中的实例,3,5-二苯基取代的1,2,4-噻二唑衍生物用作用于磷光绿色发射体的OLED中的主体材料。明确提及以下3,5-二苯基经取代1,2,4-噻二唑衍生物:
上文所提及的文献中没有一个提及所公开的化合物的TADF(热激活延迟荧光)特征。
发明内容
本发明的一个目标为提供高效且实际上有用的有机发光元件和适合于提供有机发光元件的有机材料。
已出人意料地发现某些特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物和1,2,4-噻二唑衍生物通常在298K下发射延迟荧光,且适用于提供具有高效率的有机发光元件。先前提及的298K的温度意指根据本发明的式(I)和(I')的特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物和1,2,4-噻二唑衍生物在室温(298K)下显示延迟荧光且不意指根据本发明的特定经取代的1,2,4-三唑衍生物、1,2,4-噁二唑衍生物和1,2,4-噻二唑衍生物在较低温度和较高温度下不发射延迟荧光。
因此,本发明涉及有机发光元件,其包含含以下的发光层:
其中
X为O、S或N-Y4-R4,
Y1和Y2和Y4彼此独立地为直接键、C1-C25亚烷基或C6-C10亚芳基,其未经取代或经一或多个基团R3取代;
R1和R2彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基、未经取代或经一或多个基团R3或式(Xa)或(Xd)的基团取代的C6-C14芳基;优选地,R1和R2彼此独立地为氢、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C10芳基,或式(Xa)或(Xd)的基团;
R3为氘、F、Cl、C1-C25烷基、C1-C25烷氧基、C6-C14芳氧基或C6-C14芳基;优选地,R3为C1-C25烷基、C1-C25烷氧基、C6-C10芳氧基或C6-C14芳基;
R4为C1-C25烷基、未经取代或经一或多个基团R3取代的C6-C10芳基或式(Xa)或(Xd)的基团;
X1为O、S、N(R15)、C(=O)、C(R16)(R17)、B(R18)或Si(R19)(R20);优选地,X1为O、S、C(O)、N(R15)或C(R16)(R17);
R10、R11、R21和R21'彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基,或未经取代或经一或多个基团R3取代的C6-C14芳基;优选地,R10、R11、R21和R21'彼此独立地为氢或C1-C25烷基;
R15、R16、R17、R18、R19和R20彼此独立地为C1-C25烷基,或C6-C14芳基,其未经取代或经一或多个基团R3取代;
其中至少一个式(Xa)或(Xd)的基团存在于式(I)化合物中,其特征在于发射延迟荧光。
本发明还涉及式(I)化合物用于产生延迟荧光发射的用途。
热激活延迟荧光(TADF,E型延迟荧光)是通过反向系统间窜跃(RISC)机制将自旋禁止的三重态激子向上转换为单重态能级来获得高效率的激子形成的有前景方式。在TADF发射极中,上转换机制使用在足够高温(通常约298K)下允许OLED中的所有激子经由单重态衰变最终产生光的电子振动能量。
E型延迟荧光在本文中定义为一个过程,其中第一激发单重态(S1)通过从第一激发三重态(T1)的热激活的无辐射跃迁变满。
本发明还涉及一种有机发光元件,其在发光层中包含式(I)化合物,其特征在于发射延迟荧光。
有机发光元件优选地提供大于5%、尤其大于10%的外部量子效率。另外,本发明的有机发光元件显示高亮度下减少的效率滚降特征。
式(I)化合物的激发单重态能(S1)与激发三重态能(T1)之间的差异(ΔEST)优选地为0.5eV或更小,ΔEST更优选地为0.35eV或更小,即0.01到0.5eV,尤其0.01到0.35eV。
在本发明的含义中,包含含式(I)化合物的发光层的有机发光元件的特征在于其发射延迟荧光,优选地为包含含式(I)化合物的发光层的有机发光元件,其中式(I)化合物具有0.5eV或更小的激发单重态能(S1)与激发三重态能(T1)之间的差异(ΔEST)、更优选地0.35eV或更小的ΔEST,即0.01到0.5eV、尤其0.01到0.35eV的ΔEST。
ΔEST的测定可通过量子机械计算(例如TD-DFT(时间相关性密度泛函理论)计算,例如用可商购的高斯(Gaussian)09或ADF阿姆斯特丹密度泛函(AmsterdamDensityFunctional)软件程序;例如如先进材料(Adv.Mater.)2008,20,3325-3330中所述)或以实验方式进行。
ΔEST的实验性测定:
i)
ΔEST可基于下式给出的信息测定:Int(S1→S0)/Int(T1→T0)=k(S1)/k(T1)exp(-ΔE/kBT)。
强度Int(S1→S0)和Int(T1→T0)可以光谱方式由分光光度计测定。
在不同温度下测量的对数强度比Int(S1→S0)/Int(T1→T0)相对于绝对温度T的倒数的图式一般展示为直线。测量在室温(300K)到77K到4.2K的温度范围中进行(温度可借助于低温恒温器调节)。可鉴别相应跃迁(S1→S0)和(T1→T0)(带强度),因为三重态跃迁比单重态跃迁能量低且其强度在温度降低时提高。测量通常在无氧稀溶液(约10-2molL-1)或相应化合物薄膜或包含相应化合物的掺杂膜中进行。
上述直线的斜率为-ΔE/kBT。kB=1.380 10-23JK-1=0.695cm-1K-1时,可测定ΔEST。
ii)
如所属领域的技术人员所已知,也可通过测量发射衰变的温度相关性测定ΔEST。
iii)
可通过在低温(例如77K或4.2K,使用低温恒温器)下记录荧光和磷光光谱实现ΔEST的近似估计。接着ΔEST对应于荧光或磷光带的高能上升边缘之间的能量差近似值。
当X为O或S时,式(I)化合物含有一组或两组式(Xa)和/或(Xd)。
当X为N-Y4-R4时,式(I)化合物含有两组或三组式(Xa)和/或(Xd)。
在式(I)化合物中,残基和符号具有以下含义:
X为O、S或N-Y4-R4。
Y1和Y2和Y4彼此独立地为直接键、C1-C25亚烷基或C6-C10亚芳基,其未经取代或经一或多个基团R3取代;优选地为直接键,或C6-C10亚芳基,其未经取代或经一或多个C1-C25烷基取代。C6-C10亚芳基的实例为亚苯基和亚萘基。优选的C6-C10亚芳基为1,3-亚苯基和3,6-亚萘基,其可未经取代或经一或多个C1-C8烷基取代。Y1和Y2和Y4更优选地为直接键,或式的基团。
R1和R2彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基、未经取代或经一或多个基团R3或式(Xa)或(Xd)的供体基团取代的C6-C14芳基;优选地,R1和R2彼此独立地为氢、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C10芳基,或式 的基团;
R3为氘、F、Cl、C1-C25烷基、C1-C25烷氧基、C6-C14芳氧基或C6-C14芳基;优选地,R3为C1-C25烷基、C1-C25烷氧基、C6-C14芳氧基或C6-C14芳基;更优选地,R3为C1-C25烷基或C1-C25烷氧基。
X1为O、S、N(R15)、C(=O)、C(R16)(R17)、B(R18)或Si(R19)(R20);优选地,X1为O、S、C(O)、N(R15)或C(R16)(R17);更优选地,X1为O、S、C(CH3)(CH3)、C(=O)或
R10、R11、R21和R21'彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基,或未经取代或经一或多个基团R3取代的C6-C14芳基;优选地,R10、R11、R21和R21'彼此独立地为氢或C1-C25烷基。
R15、R16、R17、R18、R19和R20彼此独立地为C1-C25烷基,或C6-C14芳基,其未经取代或经一或多个基团R3取代;优选地,R15和R18彼此独立地为式 的基团;且R16、R17、R19和R20彼此独立地为氢或C1-C25烷基;
R22和R23彼此独立地为氢、C1-C25烷基、C1-C25烷氧基、C6-C10芳氧基或C6-C10芳基;优选地为氢。
式(Xd)的基团优选地为式(Xd)的基团,其中R21和R21'为氢。
在尤其优选的式(I)化合物中,残基具有以下含义:
R1和R2彼此独立地为氢、C1-C25烷基、C6-C10芳基或式(Xa)或(Xd)的基团;
R4为C1-C25烷基、C6-C10芳基或式(Xa)或(Xd)的基团;
R10、R11、R21和R21'彼此独立地为氢,或C1-C25烷基;
其中至少一个式(Xa)或(Xd)的基团存在于式(I)化合物中。
式(I)化合物(其中X为N-Y4-R4)的特定实例为以下式(Ia)化合物:
在式(Ia)化合物中,优选的为尤其经式 的基团(Xa)和/或(Xd)取代的那些,如化合物(A-1)、(A-2)、(A-5)、(A-6)、(A-10)、(A-11)、(A-12)、(A-15)、(A-16)、(A-20)、(A-21)、(A-22)、(A-25)、(A-26)、(A-30)、(A-31)、(A-32)、(A-35)、(A-36)、(A-40)、(A-41)、(A-42)、(A-45)、(A-46)、(A-50)、(A-51)、(A-52)、(A-55)、(A-56)、(A-60)、(A-61)、(A-62)、(A-65)、(A-66)、(A-70)、(A-71)、(A-72)、(A-73)、(A-75)、(A-76)、(A-78)、(A-81)(A-82)、(A-83)、(A-84)、(A-85)、(A-86)、(A-87)、(A-88)、(A-89)、(A-90)、(A-91)、(A-92)、(A-93)、(A-94)、(A-99)和(A-100)。
最优选实例为(A-1)、(A-2)、(A-5)、(A-6)、(A-11)、(A-12)、(A-15)、(A-16)、(A-21)、(A-22)、(A-25)、(A-26)、(A-31)、(A-32)、(A-35)、(A-36)、(A-41)、(A-42)、(A-45)、(A-46)、(A-51)、(A-52)、(A-55)、(A-56)、(A-61)、(A-62)、(A-65)、(A-66)、(A-72)、(A-73)、(A-76)、(A-82)、(A-83)、(A-84)和(A-85)。
式(I)化合物(其中X为O)的特定实例为以下式(Ib)化合物:
在式(Ib)化合物中,优选的为尤其经式 的供体基团取代的那些,如化合物(B-1)、(B-2)、(B-5)、(B-6)、(B-10)、(B-21)、(B-22)、(B-25)、(B-26)、(B-30)、(B-31)、(B-32)、(B-35)、(B-36)、(B-40)、(B-75)、(B-76)、(B-78)、(B-81)、(B-82)、(B-83)、(B-86)、(B-87)、(B-88)、(B-89)、(B-90)、(B-92)、(B-93)、(B-99)和(B-100)。
最优选实例为(B-1)、(B-2)、(B-5)、(B-6)、(B-21)、(B-22)、(B-25)、(B-26)、(B-31)、(B-32)、(B-35)、(B-36)、(B-76)、(B-82)和(B-83)。
式(I)化合物(其中X为O)的特定实例为以下式(Ic)化合物:
在式(Ic)化合物中,优选的为尤其经式 的供体基团取代的那些,如化合物(C-1)、(C-2)、(C-5)、(C-6)、(C-10)、(C-21)、(C-22)、(C-25)、(C-26)、(C-30)、(C-31)、(C-32)、(C-35)、(C-36)、(C-40)、(C-75)、(C-76)、(C-81)(C-82)、(C-83)、(C-86)、(C-87)、(C-88)、(C-89)、(C-90)、(C-92)、(C-93)、(C-99)和(C-100)。
最优选实例为(C-1)、(C-2)、(C-5)、(C-6)、(C-21)、(C-22)、(C-25)、(C-26)、(C-31)、(C-32)、(C-35)、(C-36)、(C-76)、(C-82)和(C-83)。
C1-C25烷基,优选地C1-C18烷基通常为直链或分支链(在可能时)。实例为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基、正壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基或十八烷基。C1-C8烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、正己基、正庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基。C1-C4烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基。
C1-C25烷氧基,优选地C1-C18烷氧基为直链或分支链烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基或叔戊氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基和十八烷氧基。C1-C8烷氧基的实例为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、正戊氧基、2-戊氧基、3-戊氧基、2,2-二甲基丙氧基、正己氧基、正庚氧基、正辛氧基、1,1,3,3-四甲基丁氧基和2-乙基己氧基,优选地为C1-C4烷氧基,通常如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基。
C6-C10芳基(其任选地可经取代)通常为苯基、萘基(尤其为1-萘基或2-萘基)或联苯基,其可未经取代或经一或多个C1-C8烷基、C1-C8烷氧基和/或C6-C10芳氧基,尤其C1-C8烷基、C1-C8烷氧基取代。
任选地可经一或多个C1-C8烷基和/或C1-C8烷氧基取代的C6-C10芳氧基通常为苯氧基、1-萘氧基或2-萘氧基。
X为O、S、N-Y4'-R4或N-Y4”-R4,
Y1和Y2彼此独立地为直接键、C1-C25亚烷基或C6-C10亚芳基,其未经取代或经一或多个基团R3取代;
Y4'为直接键、C1-C25亚烷基;
Y4”为C6-C10亚芳基,其未经取代或经一或多个基团R3取代;
R1和R2彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基、未经取代或经一或多个基团R3取代的C6-C14芳基或式(Xa)或(Xd)的基团;
R3为氘、F、Cl、C1-C25烷基、C1-C25烷氧基、C6-C14芳氧基或C6-C14芳基;
R4为C1-C25烷基、未经取代或经一或多个基团R3取代的C6-C10芳基或式(Xa)或(Xd)的基团;
X1为O、S、N(R15)、C(=O)、C(R16)(R17)、B(R18)或Si(R19)(R20),或
当X为N-Y4”-R4时,
X1为N(R15')、C(=O)、C(R16)(R17)、B(R18)或Si(R19)(R20),
R10、R11、R21和R21'彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基或未经取代或经一或多个基团R3取代的C6-C14芳基;
R15、R16、R17、R18、R19和R20彼此独立地为C1-C25烷基,或C6-C14芳基,其未经取代或经一或多个基团R3取代;
R15'为C6-C14芳基,其未经取代或经一或多个基团R3取代;
其中至少一个式(Xa)或(Xd)的基团存在于式(I)化合物中。
式(I')的特定化合物的优选和尤其优选的残基和基团X、X1、Y1、Y2、R1、R2、R3、R4、R10、R11、R21、R21'、R15、R16、R17、R18、R19和R20与关于上文提及的式(I)化合物所提及为相同残基。
Y4'为直接键、C1-C25亚烷基,优选地直接键;且
Y4”为C6-C10亚芳基,其未经取代或经一或多个基团R3(R3如上文所定义)取代;优选地C6-C10亚芳基,其未经取代或经一或多个C1-C25烷基取代。C6-C10亚芳基的实例为亚苯基和亚萘基。优选的C6-C10亚芳基为1,3-亚苯基和3,6-亚萘基,其可未经取代或经一或多个C1-C8烷基取代。更优选地,Y4”为式的基团。
式(I')的特定化合物(其中X为N-Y4”-R4)中的X1
式(I')的特定化合物中的R15'为C6-C14芳基,其未经取代或经一或多个基团R3取代,优选地C6-C10芳基,其未经取代或经一或多个基团R3取代,更优选地式 的基团,其中R22和R23彼此独立地为氢、C1-C25烷基、C1-C25烷氧基、C6-C10芳氧基或C6-C10芳基;
最优选地苯基。
式(I')的特定化合物(其中X为N-Y4”-R4)中的基团(Xa)因此最优选地为:
式(I')化合物(其中X为N-Y4'-R4或N-Y4'-R4”)的特定实例为以下式(1'a)化合物:
(A-1)、(A-2)、(A-3)、(A-4)、(A-5)、(A-6)、(A-7)、(A-8)、(A-9)、(A-10)、(A-13)、(A-15)、(A-16)、(A-17)、(A-18)、(A-19)、(A-20)、(A-23)、(A-25)、(A-26)、(A-27)、(A-28)、(A-29)、(A-30)、(A-33)、(A-35)、(A-36)、(A-37)、(A-38)、(A-39)、(A-40)、(A-43)、(A-45)、(A-46)、(A-47)、(A-48)、(A-49)、(A-50)、(A-51)、(A-52)、(A-53)、(A-54)、(A-55)、(A-56)、(A-57)、(A-58)、(A-59)、(A-60)、(A-61)、(A-62)、(A-63)、(A-64)、(A-65)、(A-66)、(A-67)、(A-68)、(A-69)、(A-70)、(A-71)、(A-72)、(A-73)、(A-74)、(A-75)、(A-76)、(A-77)、(A-78)、(A-79)、(A-80)、(A-81)、(A-82)、(A-83)、(A-86)、(A-87)、(A-88)、(A-89)、(A-90)、(A-94)、(A-95)、(A-96)、(A-97)、(A-98)、(A-99)和(A-100)。
在式(Ia)化合物中,优选的为尤其经式 的基团(Xa)和/或(Xd)取代的那些,如化合物(A-1)、(A-2)、(A-5)、(A-6)、(A-10)、(A-15)、(A-16)、(A-20)、(A-25)、(A-26)、(A-30)、(A-35)、(A-36)、(A-40)、(A-45)、(A-46)、(A-50)、(A-51)、(A-52)、(A-55)、(A-56)、(A-60)、(A-61)、(A-62)、(A-65)、(A-66)、(A-70)、(A-71)、(A-72)、(A-73)、(A-75)、(A-76)、(A-78)、(A-81)(A-82)、(A-83)、(A-86)、(A-87)、(A-88)、(A-89)、(A-90)、(A-94)、(A-99)和(A-100)。
最优选实例为(A-1)、(A-2)、(A-5)、(A-6)、(A-15)、(A-16)、(A-25)、(A-26)、(A-35)、(A-36)、(A-45)、(A-46)、(A-51)、(A-52)、(A-55)、(A-56)、(A-61)、(A-62)、(A-65)、(A-66)、(A-72)、(A-73)、(A-76)、(A-82)和(A-83)。
式(I')化合物(其中X为O)的特定实例为以下式(I'b)化合物:
(B-1)、(B-2)、(B-3)、(B-4)、(B-5)、(B-6)、(B-7)、(B-8)、(B-9)、(B-10)、(B-21)、(B-22)、(B-23)、(B-24)、(B-25)、(B-26)、(B-27)、(B-28)、(B-29)、(B-30)、(B-31)、(B-32)、(B-33)、(B-34)、(B-35)、(B-36)、(B-37)、(B-38)、(B-39)、(B-40)、(B-75)、(B-76)、(B-77)、(B-78)、(B-79)、(B-80)、(B-81)、(B-82)、(B-83)、(B-84)、(B-85)、(B-86)、(B-87)、(B-88)、(B-89)、(B-90)、(B-92)、(B-93)、(B-95)、(B-96)、(B-97)、(B-98)、(B-99)和(B-100)。
在式(1'b)化合物中,优选的为尤其经式 的供体基团取代的那些,如化合物(B-1)、(B-2)、(B-5)、(B-6)、(B-10)、(B-21)、(B-22)、(B-25)、(B-26)、(B-30)、(B-31)、(B-32)、(B-35)、(B-36)、(B-40)、(B-75)、(B-76)、(B-78)、(B-81)、(B-82)、(B-83)、(B-86)、(B-87)、(B-88)、(B-89)、(B-90)、(B-92)、(B-93)、(B-99)和(B-100)。
最优选实例为(B-1)、(B-2)、(B-5)、(B-6)、(B-21)、(B-22)、(B-25)、(B-26)、(B-31)、(B-32)、(B-35)、(B-36)、(B-76)、(B-82)和(B-83)。
式(I')化合物(其中X为O)的特定实例为以下式(1'c)化合物:
(C-1)、(C-2)、(C-3)、(C-4)、(C-5)、(C-6)、(C-7)、(C-8)、(C-9)、(C-10)、(C-21)、(C-22)、(C-23)、(C-24)、(C-25)、(C-26)、(C-27)、(C-28)、(C-29)、(C-30)、(C-31)、(C-32)、(C-33)、(C-34)、(C-35)、(C-36)、(C-37)、(C-38)、(C-39)、(C-40)、(C-75)、(C-76)、(C-77)、(C-78)、(C-79)、(C-80)、(C-81)、(C-82)、(C-83)、(C-84)、(C-85)、(C-86)、(C-87)、(C-88)、(C-89)、(C-90)、(C-92)、(C-93)、(C-95)、(C-96)、(C-97)、(C-98)、(C-99)和(C-100)。
在式(1'c)化合物中,优选的为尤其经式 的供体基团取代的那些,如化合物(C-1)、(C-2)、(C-5)、(C-6)、(C-10)、(C-21)、(C-22)、(C-25)、(C-26)、(C-30)、(C-31)、(C-32)、(C-35)、(C-36)、(C-40)、(C-75)、(C-76)、(C-81)、(C-82)、(C-83)、(C-86)、(C-87)、(C-88)、(C-89)、(C-90)、(C-92)、(C-93)、(C-99)和(C-100)。
最优选实例为(C-1)、(C-2)、(C-5)、(C-6)、(C-21)、(C-22)、(C-25)、(C-26)、(C-31)、(C-32)、(C-35)、(C-36)、(C-76)、(C-82)和(C-83)。
另外,本发明涉及一种包含式(I')的特定化合物的有机发光元件。
另外,本发明涉及一种包含含式(I')的特定化合物的发光层的发光元件。
对于式(I')的特定化合物,上文指定的偏好适用。
式(I')的特定化合物或式(I)化合物可用作有机EL元件的发光层中与荧光客体材料组合的主体。已知荧光材料可用作荧光客体材料。荧光客体材料的实例包括双芳氨基萘衍生物、芳基取代的萘衍生物、双芳氨基蒽衍生物、芳基取代的蒽衍生物、双芳氨基芘衍生物、芳基取代的芘衍生物、双芳氨基屈衍生物、芳基取代的屈衍生物、双芳氨基丙二烯合芴衍生物、芳基取代的丙二烯合芴衍生物、茚并叵衍生物、吡咯亚甲基硼复合化合物、具有吡咯亚甲基构架的化合物或其金属络合物、二酮基吡咯并吡咯衍生物和苝衍生物。实例为2,5,8,11-四-叔丁基苝(TBPe)、9,10-双[N,N-二-(对甲苯基)-氨基]蒽(TTPA)、2,8-二-叔丁基-5,11-双(4-叔丁基苯基)-6,12-二苯基并四苯(TBRb)和二苯并{[f,f']-4,4',7,7'-四苯基}二茚并1,2,3-cd:1',2',3'-lm]苝(DBP)。在使用式(I')的特定化合物或式(I)化合物作为主体材料的情况下,发光层中的式(I')化合物或式(I)化合物的含量优选地落入按发光层的总重量计51到99重量%、更优选地80到99重量%的范围内。
本发明因此另外涉及如上所述的有机发光元件,其包含含式(I')的特定化合物作为主体和客体材料的发光层。
对于式(I')的特定化合物,上文指定的偏好适用。
或者,式(I')的特定化合物以及式(I)化合物可作为客体与主体材料组合用于有机EL元件的发光层中。所述客体化合物优选地以按发光层的总重量计1到50重量%、更优选地1重量%到25重量%、最优选地6%到15重量%的量存在于发光层中。
式(I)化合物,对应地式(I')的特定化合物,即有机发光材料优选地具有0.5eV或更小的激发单重态能与激发三重态能之间的差异(ΔEST)、更优选地0.35eV或更小,即0.01到0.5eV,尤其0.01到0.35eV的ΔEST。式(I)化合物或式(I')的特定化合物可在发光层中单独用作有机发光材料。然而视需要,出于例如在有机发光材料中限制有机发光材料中产生的单重态激子和三重态激子的目的,优选地将本发明的有机发光材料和如下有机化合物用于发光层:所述化合物的激发单重态能和激发三重态能中的至少任一个的值比所述有机发光材料的那些值高且充当主体材料。主体化合物的激发单重态能(S1h)和激发三重态能(T1h)中的至少任一个优选地比本发明的有机发光材料的激发单重态能(S1g)和激发三重态能(T1g)高0.1eV或更大,尤其优选地高0.2eV或更大。也就是说,优选地满足(S1h)-(S1g)>0.1eV和(T1h)-(T1g)>0.1eV中的一个或两个,且更优选地满足(S1h)-(S1g)>0.2eV和(T1h)-(T1g)>0.2eV中的一个或两个。在使用式(I)化合物或式(I')的特定化合物作为客体材料的情况下,发光层中的式(I)化合物或式(I')的特定化合物的含量优选地落入按发光层的总重量计1到50重量%、更优选地1到25重量%、最优选地6到15重量%范围内。
本发明因此另外涉及上所述的有机发光元件,其包含含作为主体的式(I')的特定化合物和客体材料的发光层。
对于式(I')的特定化合物,上文指定的偏好适用。
本发明的有机EL元件(有机发光元件)通常具有阳极、空穴传输层、发光层和阴极作为必需的层。
另外,除通常必需的层以外,本发明的有机EL元件还可具有电子传输层、电子注入层、电子阻挡层、空穴阻挡层和激子元件层作为除通常必需的层以外的层。此外,空穴传输层可为具有空穴注入功能的空穴注入/传输层,且电子传输层可为具有电子注入功能的电子注入/传输层。
有机EL元件的实例因此包含至少以下层:阳极、空穴传输层、发光层、电子传输层和阴极。
本发明的有机EL元件可以此顺序包含:衬底、阳极、空穴注入层、空穴传输层、发光层、电子传输层和阴极。或者,阴极、电子传输层、发光层、空穴传输层和阳极可以所述顺序层压于衬底上。
衬底
本发明的有机EL元件优选地由衬底支撑。衬底不受特定限制且可为常规用于有机EL元件的任何衬底。举例来说,可使用由玻璃、透明塑料、石英等形成的衬底。
阳极
优选地用作有机EL元件中的阳极者为使用具有高功函数(4eV或更大)的金属、掺杂物、导电化合物和其混合物中的任一种作为电极物质者。此类电极物质的特定实施例包括如Au的金属和导电透明材料,如CuI、氧化铟锡(ITO)、SnO2和ZnO。另外,可使用能够制造非晶形透明导电膜(如IDIXO(In2O3-ZnO))的材料。在阳极的生产中,有可能通过如蒸气沉积或溅镀的方法使那些电极物质中的任一种形成薄膜,且接着通过光刻方法形成具有所要形状的图案。或者,在使用如有机导电化合物的可涂布物质的情况下,还有可能采用印刷模式、涂布模式等的湿式成膜法。
阴极
同时,优选地用作阴极者为使用具有低功函数(4eV或更小)的金属(称为电子注入金属)、掺杂物、导电化合物和其混合物中的任一种作为电极物质者。此类电极物质的特定实例包括钠、钠钾合金、镁、锂、镁/铜混合物、镁/银混合物、镁/铝混合物、镁/铟混合物、铝/氧化铝(Al2O3)混合物、铟、锂/铝混合物和稀土金属。其中,从电子注入特性和相对于氧化及等的耐久性的观点出发,电子注入金属和第二金属(其功函数值比电子注入金属的功函数值高且为稳定金属)的混合物,如镁/银混合物、镁/铝混合物、镁/铟混合物、铝/氧化铝(Al2O3)混合物、锂/铝混合物或铝为合适的。应注意,有机EL元件的阳极和阴极中的任一个透明或半透明以传输发射光的情况为有利的,因为光发射亮度提高。
发光层
发光层为在已经由使分别从阳极和阴极注入的空穴和电子重组产生激子之后发光的层。发光层优选地包括有机发光材料和主体材料。作为有机发光材料,可使用选自式(I)化合物,对应地选自式(I')的特定化合物的一类或两类或多于两类。为了使本发明的有机EL元件展现高发光效率,在有机发光材料中限制有机发光材料中产生的单重态激子和三重态激子为重要的。因此,优选地在发光层中使用除有机发光材料以外的主体材料。作为主体材料,可使用激发单重态能和激发三重态能中的至少任一个的值比本发明的有机发光材料的那些值高的有机化合物。这使得本发明的有机发光材料中产生的单重态激子和三重态激子在本发明的有机发光材料分子中受限制且使得发光效率得到充分展现。在本发明的有机EL元件中,光从包括于发光层中的本发明的有机发光材料发射。
在使用以下主体材料的情况下,发光层中的本发明的有机发光材料的含量优选地落入按发光层的总重量计1到50重量%、更优选地1到25重量%、最优选地6到15重量%的范围内。
发光层中的主体材料优选地为有机化合物,其具有空穴传输能力和/或电子传输能力,预防发射波长变得较长,且具有高玻璃转化温度。
主体材料可为聚合物,例如聚(N-乙烯基咔唑)或聚硅烷。但是,主体材料可为小分子,例如4,4-N,N-二咔唑联苯(CDP=CBP)、2,6-双(N-咔唑基)苯基(mCP)、3,3-二(9H-咔唑-9-基)联苯(mCBP)、(PYD2)、(DPEPO)、(PPT)、(UGH-2)、(TPSi-F)、(CzSi)、(TmPyPB)、(2,4,6-三(联苯-3-基)-1,3,5-三嗪(T2T))
或叔芳族胺,例如TCTA。
但是,如上所述,式(I)化合物以及式(I')的特定化合物可替代地用作有机EL元件的发光层中与荧光客体材料组合的主体。已知荧光材料可用作荧光客体材料。适合的荧光材料为上文所提及的。
注入层
注入层是指出于降低驱动电压和提高发光亮度的目的而在电极与有机层之间提供的层。注入层包括空穴注入层和电子注入层,且可提供于阳极与发光层或空穴传输层之间,和阴极与发光层或电子传输层之间。可视需要提供注入层。
惯用空穴注入材料包括CuPc、MTDATA或二吡嗪并[2,3-f:2',3'-h]喹喔啉-2,3,6,7,10,11-六甲腈(HAT-CN)。可使用聚合空穴注入材料,如聚(N-乙烯基咔唑)(PVK);聚噻吩;聚吡咯;聚苯胺;自掺杂聚合物,如磺化聚(噻吩-3-[2[(2-甲氧基乙氧基)乙氧基]-2,5-二基)(可商购自Plextronics的OC导电油墨);和共聚物,例如也被称为PEDOT/PSS的聚(3,4-亚乙二氧基噻吩)/聚(4-苯乙烯磺酸酯)。
包含锂的有机金属化合物(如8-羟基喹啉基锂(Liq))、CsF、NaF、KF、Cs2CO3或LiF可作为电子注入层涂覆在电子输送层与阴极之间以便降低操作电压。
阻挡层
阻挡层能够阻挡发光层中存在的电荷(电子或空穴)和/或激子扩散至发光层外。电子阻挡层可布置于发光层与空穴传输层之间,且阻挡电子穿过发光层接近空穴传输层。同样,空穴阻挡层可布置在发光层与电子传输层之间,且阻挡空穴穿过发光层接近电子传输层。阻挡层也可用于阻挡激子扩散至发光层外。即电子阻挡层和空穴阻挡层也可各自具有激子阻挡层的功能。如本文所用,电子阻挡层或激子阻挡层意图包括在一个层中具有电子阻挡层和激子阻挡层的功能的层。
空穴阻挡层
从广义来说,空穴阻挡层具有电子传输层的功能。空穴阻挡层具有阻挡空穴到达电子传输层同时传输电子的作用。这可提高电子和空穴在发光层中重组的机率。作为用于空穴阻挡层的材料,可视需要使用下文所述的用于电子传输层的材料。
电子阻挡层
从广义来说,电子阻挡层具有传输空穴的功能。电子阻挡层具有阻挡电子到达空穴传输层同时传输空穴的作用。这可提高电子和空穴在发光层中重组的机率。
激子阻挡层
激子阻挡层是指用于阻挡激子扩散至电荷传输层的层,其通过发光层中空穴和电子的重组产生。此层的插入使得激子在发光层中有效地受限制,其可提高元件的发光效率。激子阻挡层可插入相邻发光层的阳极侧和阴极侧中的任一侧上,且可同时插入两侧上。即当激子阻挡层提供于阳极侧上时,所述层可插入空穴传输层与发光层之间以便与发光层相邻。当激子阻挡层插入阴极侧上时,所述层可插入发光层与阴极之间以便与发光层相邻。另外,空穴注入层、电子阻挡层等可提供于阳极与激子阻挡层(其与发光层的阳极侧相邻)之间,且电子注入层、电子传输层、空穴阻挡层等可提供于阴极与激子阻挡层(其与发光层的阴极侧相邻)之间。在提供阻挡层的情况下,优选的是用作阻挡层的材料的激发单重态能和激发三重态能中的至少任一个比发光材料的激发单重态能和激发三重态能高。
通常使用的空穴阻挡材料为2,6-双(N-咔唑基)吡啶(mCPy)、2,9-二甲基-4,7-二苯基-1,10-啡啉(浴铜灵(bathocuproin,BCP))、双(2-甲基-8-喹啉根基)-4-苯基苯氧基)铝(III)(BAlq)、啡噻嗪S,S-二氧化物衍生物和1,3,5-三(N-苯基-2-苄基咪唑基)苯)(TPBI),TPBI也适用作电子传输材料。其它适合的空穴阻挡和/或电子导体材料为2,2',2”-(1,3,5-苯次甲基)三(1-苯基-1-H-苯并咪唑)、2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑、8-羟基喹啉锂、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、1,3-双[2-(2,2'-二吡啶-6-基)-1,3,4-噁二唑-5-基]苯、4,7-二苯基-1,10-啡啉、3-(4-联苯基)-4-苯基-5-叔丁基苯基-1,2,4-三唑、6,6'-双[5-(联苯基-4-基)-1,3,4-噁二唑-2-基]-2,2'-二吡啶基、2-苯基-9,10-二(萘-2-基)蒽、2,7-双[2-(2,2'-二吡啶-6-基)-1,3,4-噁二唑-5-基]-9,9-二甲基芴、1,3-双[2-(4-叔丁基苯基)-1,3,4-噁二唑-5-基]苯、2-(萘-2-基)-4,7-二苯基-1,10-啡啉、三(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、2,9-双(萘-2-基)-4,7-二苯基-1,10-啡啉、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑并[4,5-f][1,10]啡啉、(DPEPO)。
空穴传输层
空穴传输层由具有传输空穴功能的空穴传输材料形成。空穴传输层可以单层或多层提供。
空穴传输材料具有空穴注入或传输特性和电子阻挡特性中的任一个,且可为有机材料或无机材料。适用的已知空穴传输材料由三唑衍生物、噁二唑衍生物、咪唑衍生物、咔唑衍生物、吲哚并咔唑衍生物、聚芳烷衍生物、吡唑啉衍生物、二氢吡唑酮衍生物、苯二胺衍生物、芳胺衍生物、胺基取代的查耳酮衍生物、噁唑衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、芪衍生物、硅氮烷衍生物、基于苯胺的共聚物或导电聚合寡聚物(尤其噻吩寡聚物)例示。但是,优选使用的为卟啉化合物、芳族叔胺化合物和苯乙烯胺化合物,并且更优选使用的为芳族叔胺化合物。惯用的空穴传输分子选自由以下组成的群组: (4-苯基-N-(4-苯基苯基)-N-[4-[4-(N-[4-(4-苯基苯基)苯基]苯胺基)苯基]苯基]苯胺)、(4-苯基-N-(4-苯基苯基)-N-[4-[4-(4-苯基-N-(4-苯基苯基)苯胺基)苯基]苯基]苯胺)、(4-苯基-N-[4-(9-苯基咔唑-3-基)苯基]-N-(4-苯基苯基)苯胺)、(1,1',3,3'-四苯基螺[1,3,2-苯并二氮杂硅罗-2,2'-3a,7a-二氢-1,3,2-苯并二氮杂硅罗])、(N2,N2,N2',N2',N7,N7,N7',N7'-八(对甲苯基)-9,9'-螺二[芴]-2,2',7,7'-四胺)、4,4'-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)、N,N'-二苯基-N,N'-双(3-甲基苯基)-[1,1'-联苯]-4,4'-二胺(TPD)、1,1-双[(二-4-甲苯氨基)苯基]环己烷(TAPC)、N,N'-双(4-甲基苯基)-N,N'-双(4-乙基苯基)-[1,1'-(3,3'-二甲基)联苯]-4,4'-二胺(ETPD)、四(3-甲基苯基)-N,N,N',N'-2,5-苯二胺(PDA)、α-苯基-4-N,N-二苯基氨基苯乙烯(TPS)、对(二乙氨基)苯甲醛二苯基腙(DEH)、三苯胺(TPA)、双[4-(N,N-二乙氨基)2-甲基苯基](4-甲基苯基)甲烷(MPMP)、1-苯基-3-[对(二乙氨基)苯乙烯基]5-[对(二乙氨基)苯基]吡唑啉(PPR或DEASP)、1,2-反-双(9H-咔唑-9-基)-环丁烷(DCZB)、N,N,N',N'-四(4-甲基苯基)-(1,1'-联苯)-4,4'-二胺(TTB)、氟化合物(如2,2',7,7'-四(N,N-二-甲苯基)氨基-9,9-螺二芴(螺-TTB)、N,N'-双(萘-1-基)-N,N'-双(苯基)-9,9-螺二芴(螺-NPB)和9,9-双(4-(N,N-双-联苯-4-基-氨基)苯基-9H-芴)、联苯胺化合物(如N,N'-双(萘-1-基)-N,N'-双(苯基)联苯胺)以及卟啉化合物(如铜酞菁)、(BPY-TP2)、(Tris-PCz)。另外,可使用聚合空穴注入材料,如聚(N-乙烯基咔唑)(PVK);聚噻吩;聚吡咯;聚苯胺;自掺杂聚合物,如磺化聚(噻吩-3-[2[(2-甲氧基乙氧基)乙氧基]-2,5-二基)(OC Conducting Inks,可购自Plextronics);和共聚物,如聚(3,4-亚乙二氧基噻吩)/聚(4-苯乙烯磺酸酯)(也被称为PEDOT/PSS)。
电子传输层
电子传输层由具有传输电子功能的材料形成。电子传输层可以单层或多层提供。
电子传输材料(也可充当空穴阻挡材料)仅必须具有将从阴极注入的电子传输至发光层的功能。适用的电子传输层由硝基取代的芴衍生物、二苯醌衍生物、硫代吡喃二氧化物衍生物、碳化二亚胺、亚芴基甲烷衍生物、蒽醌二甲烷衍生物、蒽酮衍生物或噁二唑衍生物例示。此外,在噁二唑衍生物中,噁二唑环的氧原子由硫原子取代的噻二唑衍生物或具有称为拉电子基团的喹喔啉环的喹喔啉衍生物也可用作电子传输材料。此外,也可使用通过将那些材料中的任一者引入至聚合物链中获得的聚合物材料或在聚合物主链中包括那些材料中的任一者的聚合物材料。适合的电子传输材料包含1,3,5-三(N-苯基-2-苄基咪唑基)苯(TPBi)、(BPY-TP2)、(PPT)、与类咢辛化合物螯合的金属(如三(8-羟基醌酸酯基)铝(Alq3))、基于啡啉的化合物(如2,9-二甲基-4,7-二苯基-1,10-啡啉(DDPA=BCP)、4,7-二苯基-1,10-啡啉(Bphen)、2,4,7,9-四苯基-1,10-啡啉、4,7-二苯基-1,10-啡啉(DPA)或EP1786050、EP1970371或EP1097981中所公开的啡啉衍生物)和唑化合物(如2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑(PBD)和3-(4-联苯基)-4苯基-5-(4-叔丁基苯基)-1,2,4-三唑(TAZ))。
可能的元件结构的实例展示如下:
ITO(100nm)/α-NPD(35nm)/CBP:6重量%式(I)化合物,对应地式(I')的特定化合物(15nm)/TPBi(65nm)/LiF(0.8nm)/Al(80nm)
ITO(100nm)/α-NPD(40nm)/mCP/PPT:6重量%式(I)化合物,对应地式(I')的特定化合物(20nm)/PPT(40nm)/LiF(0.8nm)/Al(80nm)
ITO(30-100nm)/α-NPD(60nm)/mCP:6重量%式(I)化合物,对应地式(I')的特定化合物(20nm)/Bphen(40nm)/MgAg(100nm)/Ag(20nm)
ITO(30-100nm)/α-NPD(60nm)/PYD2:6重量%式(I)化合物,对应地式(I')的特定化合物(20nm)/Bphen(40nm)/MgAg(100nm)/Al(20nm)
ITO/α-NPD(35nm)/6重量%式(I)化合物,对应地式(I')的特定化合物:CBP(15nm)/TPBi(65nm)/LiF(0.8nm)/Al(80nm)
ITO(100nm)/HAT-CN(10nm)/Tris-PCz(30nm)/CBP:3、6、10或15重量%式(I)化合物,对应地式(I')的特定化合物(30nm)/BPY-TP2(40nm)/LiF(0.8nm)/Al(100nm)
ITO(100nm)/α-NPD(35nm)/CBP(10nm)/DPEPO:6到12重量%式(I)化合物,对应地式(I')的特定化合物(15nm)/DPEPO(10nm)/TPBi(65nm)/LiF(0.5nm)/Al(80nm)]
ITO:铟/氧化锡;α-NPD:4,4'-双[N-(1-萘基)-N-苯基氨基]联苯;
CBP:4,4'-N,N'-二咔唑联苯;TPBi:1,3,5-三(N-苯基-2-苄基咪唑基)苯;
mCP:2,6-双(N-咔唑基)吡啶;PPT:Bphen:4,7-二苯基-1,10-啡啉;PYD2:HAT-CN:二吡嗪并[2,3-f:2',3'-h]喹喔啉-2,3,6,7,10,11-六甲腈;Tris-PCz:BPY-TP2:DPEPO:
有机EL元件在电场施加于所得元件的阳极与阴极之间时发光。
本发明的有机EL元件可应用于单个元件、由以阵列方式布置的结构形成的元件和阳极与阴极以X-Y矩阵方式布置的结构中的任一者。
根据本发明的有机发光元件的特征在于其通过延迟荧光发光。
根据本发明,提供通过将具有本发明的特定构架的有机发光材料并入至发射延迟荧光的发光层中而相比于使用来自单重态的光发射的常规元件具有显著提高的发光效率的元件。所述元件在涂覆于全色或多色面板时可展现极佳性能。所述元件也可用于背光、照明等。
以上式(I)化合物和以上式(I')的特定化合物可用于电子照相的感光器、光电转换器、感测器、染料激光器、太阳能电池装置和有机发光元件。本发明因此另外涉及式(I)化合物和式(I')的特定化合物用于电子照相感光器、光电转换器、传感器、染料激光器、太阳能电池装置和有机发光元件的用途。
本发明另外涉及式(I)化合物和式(I')的特定化合物用于产生延迟荧光发射的用途。
本发明的式(I)化合物和式(I')的特定化合物可使用铜催化的乌尔曼(Ullmann)条件或钯催化的布赫瓦尔德-哈特维希(Buchwald-Hartwig)条件合成。适合的苯并双噁唑、苯并双噻唑和苯并双咪唑基础构架为可商购的,或可通过所属领域的技术人员已知的方法获得。对JP10340786、KR20110085784A和KR101160670进行参考。
具体实施方式
仅出于说明的目的而包括以下实例,且不限制权利要求的范围。除非另行说明,否则所有份数和百分比是按重量计。
实例
实例1
a)将4-溴苯甲腈(56mmol)和乙醇(35g)置于100ml烧瓶中。在搅拌时缓慢添加乙酰氯(448mmol)。在室温下搅拌混合物过夜(15小时)。在反应完成之后,通过蒸发去除乙醇,接着用二乙醚洗涤残余物。通过在真空中干燥获得白色固体。(产率:84.4%)产物不经进一步纯化即用于下一反应。
b)将来自实例1a的产物(11.3mmol)、三乙胺(24.9mmol)、4-溴苯甲酰氯(11.3mmol)和35ml二氯甲烷置于100ml烧瓶中。在-15℃至室温下搅拌混合物过夜(15小时)。在反应完成之后,通过蒸发去除二氯甲烷,接着用温四氢呋喃洗涤残余物。通过在真空中干燥获得白色固体。(粗物质,产率:105%)。产物不经进一步纯化即用于下一反应。
c)将来自实例1b的产物(11.3mmol)、苯肼(12.5mmol)和70ml四氯甲烷置于100ml烧瓶中。在室温下搅拌混合物过夜(15小时)。在反应完成之后,通过蒸发去除四氯甲烷。通过柱色谱(用二氯甲烷/己烷=1/30-1/1作为洗脱剂)纯化粗产物。通过在真空中干燥获得米色固体。(产率:16.5%)。1H-NMR(ppm,CDCl3):8.09(dd,2H),7.59(dd,2H),7.52-7.39(m,9H)
d)将来自实例1c的产物(0.66mmol)、啡噁嗪(1.35mmol)、三(二亚苄基丙酮)二钯(0.013mmol)、三叔丁基膦(0.026mmol)、叔丁醇钠(1.98mmol)和7ml甲苯置于50ml烧瓶中。在110℃下搅拌混合物过夜且冷却。过滤混合物且用己烷洗涤固体,随后通过柱色谱(用二氯甲烷/己烷=1/5作为洗脱剂)纯化。通过在真空中干燥获得淡黄色固体。(产率:81.4%)。随后使用区域升华纯化产物。1H-NMR(ppm,CDCl3):8.47(d,2H),7.80(d,2H),7.52(m,5H),7.47(d,2H),7.38(d,2H),6.68(m,12H),6.01(dd,2H),5.94(dd,2H)
包含含化合物A-1的发光层的制备的有机发光二极管发射具有高外部量子效率的光。
Claims (15)
1.一种有机发光元件,其包含发光层,所述发光层包含:
其中
X为O、S或N-Y4-R4,
Y1和Y2和Y4彼此独立地为直接键、C1-C25亚烷基或C6-C10亚芳基,其未经取代或经一或多个基团R3取代;
R1和R2彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基、未经取代或经一或多个基团R3取代的C6-C14芳基或式(Xa)或(Xd)的基团;
R3为氘、F、Cl、C1-C25烷基、C1-C25烷氧基、C6-C14芳氧基或C6-C14芳基;
R4为C1-C25烷基、未经取代或经一或多个基团R3取代的C6-C10芳基或式(Xa)或(Xd)的基团;
X1为O、S、N(R15)、C(=O)、C(R16)(R17)、B(R18)或Si(R19)(R20);
R10、R11、R21和R21'彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基或未经取代或经一或多个基团R3取代的C6-C14芳基;
R15、R16、R17、R18、R19和R20彼此独立地为C1-C25烷基,或C6-C14芳基,其未经取代或经一或多个基团R3取代;
其中至少一个式(Xa)或(Xd)的基团存在于所述式(I)化合物中,其特征在于发射延迟荧光。
2.一种发光层,其包含作为客体的至少一种如权利要求1所述的式(I)化合物和主体材料;或包含作为主体的至少一种如权利要求1所述的式(I)化合物和荧光客体材料。
X为O、S、N-Y4'-R4或N-Y4”-R4,
Y1和Y2彼此独立地为直接键、C1-C25亚烷基或C6-C10亚芳基,其未经取代或经一或多个基团R3取代;
Y4'为直接键、C1-C25亚烷基;
Y4”为C6-C10亚芳基,其未经取代或经一或多个基团R3取代;
R1和R2彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基、未经取代或经一或多个基团R3取代的C6-C14芳基或式(Xa)或(Xd)的基团;
R3为氘、F、Cl、C1-C25烷基、C1-C25烷氧基、C6-C14芳氧基或C6-C14芳基;
R4为C1-C25烷基、未经取代或经一或多个基团R3取代的C6-C10芳基或式(Xa)或(Xd)的基团;
X1为O、S、N(R15)、C(=O)、C(R16)(R17)、B(R18)或Si(R19)(R20),或
当X为N-Y4”-R4时,
X1为N(R15')、C(=O)、C(R16)(R17)、B(R18)或Si(R19)(R20),
R10、R11、R21和R21'彼此独立地为氢、氘、F、Cl、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C14芳氧基或未经取代或经一或多个基团R3取代的C6-C14芳基;
R15、R16、R17、R18、R19和R20彼此独立地为C1-C25烷基,或C6-C14芳基,其未经取代或经一或多个基团R3取代;
R15'为C6-C14芳基,其未经取代或经一或多个基团R3取代;
其中至少一个式(Xa)或(Xd)的基团存在于所述式(I')化合物中。
5.根据权利要求3或4所述的化合物,其中
R1和R2彼此独立地为氢、C1-C25烷基、C1-C25烷氧基、未经取代或经一或多个基团R3取代的C6-C10芳基或式(Xa)或(Xd)的基团;
R3为C1-C25烷基、C1-C25烷氧基、C6-C10芳氧基或C6-C14芳基;
R4为C1-C25烷基、未经取代或经一或多个基团R3取代的C6-C10芳基或式(Xa)或(Xd)的基团;
X1为O、S、C(O)、N(R15)或C(R16)(R17);或
当X为N-Y4”-R4时,
X1为N(R15')或C(R16)(R17),且
R10、R11、R21和R21'彼此独立地为氢,或C1-C25烷基;
R16和R17彼此独立地为氢或C1-C25烷基;
R22和R23彼此独立地为氢、C1-C25烷基、C1-C25烷氧基、C6-C10芳氧基或C6-C10芳基;
其中至少一个式(Xa)或(Xd)的基团存在于所述式(I')化合物中。
9.一种发光层,其包含根据权利要求3到8中任一权利要求所述的化合物。
10.一种有机发光元件,其包含根据权利要求3到8中任一权利要求所述的化合物、或根据权利要求9所述的发光层。
11.根据权利要求10所述的有机发光元件,其包含含作为客体的根据权利要求3到8中任一权利要求所述的化合物和主体材料的发光层。
12.根据权利要求10所述的有机发光元件,其包含含作为主体的根据权利要求3到8中任一权利要求所述的化合物和客体材料的发光层。
13.根据权利要求1和10到12中任一权利要求所述的有机发光元件,其特征在于通过延迟荧光发光。
14.一种如权利要求1所定义或根据权利要求3到8中任一权利要求所述的化合物的用途,其用于电子照相感光器、光电转换器、传感器、染料激光器、太阳能电池装置和有机发光元件。
15.一种如权利要求1所定义或根据权利要求3到8中任一权利要求所述的化合物的用途,其用于产生延迟荧光发射。
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