CN114560809B - 一种有机化合物及其应用 - Google Patents
一种有机化合物及其应用 Download PDFInfo
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- CN114560809B CN114560809B CN202210215474.2A CN202210215474A CN114560809B CN 114560809 B CN114560809 B CN 114560809B CN 202210215474 A CN202210215474 A CN 202210215474A CN 114560809 B CN114560809 B CN 114560809B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 35
- 239000000463 material Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
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- 239000012043 crude product Substances 0.000 description 19
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 10
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
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- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
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- OCQFHFNWMCLWKC-UHFFFAOYSA-N 1-n,4-n,4-n-triphenylbenzene-1,4-diamine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 OCQFHFNWMCLWKC-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
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- LHWWETDBWVTKJO-UHFFFAOYSA-N et3n triethylamine Chemical compound CCN(CC)CC.CCN(CC)CC LHWWETDBWVTKJO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 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
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- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
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- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction 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
- 238000009210 therapy by ultrasound Methods 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
本发明提供一种有机化合物及其应用,所述有机化合物具有合适的HOMO能级与LUMO能级,具有较高的载流子传输速率以及平衡的载流子传输性能,有助于器件中空穴和电子传输的平衡同时获得较宽的载流子复合区域,提高发光效率,另外,具有良好的热稳定性和成膜性。
Description
技术领域
本发明属于有机电致发光材料技术领域,涉及一种有机化合物及其应用。
背景技术
有机电致发光材料按发光机理可分为电致荧光和电致磷光发光材料两种,电致荧光发光材料是单重态激子的辐射衰减跃迁,电致磷光发光材料则是三重态激子辐射衰减到基态所发射的光。根据自旋量子统计理论,单重态激子和三重态激子的形成概率比例是1:3。荧光材料内量子效率不超过25%,外量子效率普遍低于5%;电致磷光材料的内量子效率理论上达到100%,外量子效率可达20%。
磷光重金属材料有较长的寿命(μs),在高电流密度下,可能导致三线态-三线态湮灭和浓度淬灭,造成器件性能衰减,因此通常将重金属磷光材料掺杂到合适的主体材料中,形成一种主客体掺杂体系,使得能量传递最优化,发光效率和寿命最大化。在目前的研究现状中,重金属掺杂材料商业化已成熟,很难开发可替代的掺杂材料。因此,把重心放在研发磷光主体材料是研究者们共通的思路。
然而现有的磷光主体材料由于HOMO能级与LUMO能级与相邻层材料的能级不匹配,以及载流子运输存在明显差异,使得载流子在发光层中不平衡,导致效率滚降严重;因此,在本领域中期望开发出性能更为优良的磷光主体材料来克服所述问题。
发明内容
针对现有技术的不足,本发明的目的在于提供一种有机化合物及其应用。
为达此目的,本发明采用以下技术方案:
本发明的目的之一在于提供一种有机化合物,所述有机化合物具有如下式I所示结构:
其中X1-X12各自独立选自N或者CRa,Ra为氢、取代或未取代的C1-C10的烷基、取代或未取代的C1-C10的环烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基、OR1或SR1;
R1为取代或未取代的C1-C10的烷基、取代或未取代的C1-C10的环烷基;
L选自连接键、取代或未取代的C6-C30芳基,取代或未取代C3-C30的杂芳基;n为0-3的整数;
Ar选自取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基。
在本发明中,所述具有式I所示结构的有机化合物具有合适的HOMO能级与LUMO能级,具有较高的载流子传输速率以及平衡的载流子传输性能,有助于器件中空穴和电子传输的平衡同时获得较宽的载流子复合区域,提高发光效率,另外,具有良好的热稳定性和成膜性。
在本发明中,所述C1-C10各自独立地可以为C1、C2、C3、C4、C5、C6、C7、C8、C9、C10、
所述C6-C30各自独立地可以为C7、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
所述C3-C30各自独立地可以为C3、C5、C6、C7、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
在本发明中,所述n为0-3的整数,例如0、1、2或3。
本发明的目的之二在于提供一种有机电致发光材料,所述有机电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种OLED器件,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如目的之一所述的有机化合物。
本发明的目的之四在于提供一种显示面板,所述显示面板包括如目的之三所述的OLED器件。
本发明的目的之五在于提供一种有机发光显示装置,包括如目的之四所述的显示面板。
本发明的目的之六在于提供一种一种电子设备,所述电子设备包括如目的之四所述的显示面板。
相对于现有技术,本发明具有以下有益效果:
本发明的有机化合物具有合适的HOMO能级与LUMO能级,具有较高的载流子传输速率以及平衡的载流子传输性能,有助于器件中空穴和电子传输的平衡同时获得较宽的载流子复合区域,提高发光效率,另外,具有良好的热稳定性和成膜性。使用本发明的含内酰胺的有机化合物的OLED器件具有高寿命、高效率、低工作电压和高色纯度。
附图说明
图1为本发明提供的OLED器件的结构示意图,其中1为基板、2为ITO阳极,3为空穴注入层、4为空穴传输层(包括第一空穴传输层41和第二空穴传输层42)、5为发光层、6为电子传输层、7为电子注入层、8为阴极,9为盖帽层9,箭头方向表示出光方向。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明的目的之一在于提供一种有机化合物,所述有机化合物具有如下式I所示结构:
其中X1-X12各自独立选自N或者CRa,Ra为氢、取代或未取代的C1-C10的烷基、取代或未取代的C1-C10的环烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基、OR1或SR1;
R1为取代或未取代的C1-C10的烷基、取代或未取代的C1-C10的环烷基;
L选自连接键、取代或未取代的C6-C30芳基,取代或未取代C3-C30的杂芳基;n为0-3的整数;
Ar选自取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基。
在本发明中,所述具有式I所示结构的有机化合物具有合适的HOMO能级与LUMO能级,具有较高的载流子传输速率以及平衡的载流子传输性能,有助于器件中空穴和电子传输的平衡同时获得较宽的载流子复合区域,提高发光效率,另外,具有良好的热稳定性和成膜性。
在本发明中,所述C1-C10各自独立地可以为C1、C2、C3、C4、C5、C6、C7、C8、C9、C10、
所述C6-C30各自独立地可以为C7、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
所述C3-C30各自独立地可以为C3、C5、C6、C7、C8、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
在本发明中,所述n为0-3的整数,例如0、1、2或3。
在一个实施方案中,所述取代的C1-C10的烷基、取代的C1-C10的环烷基、取代的C6-C30的芳基或取代的C3-C30的杂芳基中取代基为氘、氟、三氟甲基、氰基、甲基、乙基、叔丁基、异丙基或甲氧基。
在一个实施方案中,X1-X12均为CRa,Ra为氢、取代或未取代C1-C10的烷基、取代或未取代C1-C10的环烷基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基。
在一个实施方案中,X1-X12中至少一者为N。
在一个实施方案中,L选自单键、亚苯基、亚联苯基或亚萘基。
在一个实施方案中,Ar选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的吡啶基或取代或未取代的三嗪基;
当为所述取代的基团时,取代基选自C1-C10的烷基或C6-C30的芳基。
在一个实施方案中,所述有机化合物为如下化合物中的任意一种:
其中D代表氘。
在本发明中,所述有机化合物的制备方法如下:
本发明的目的之二在于提供一种有机电致发光材料,所述有机电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种OLED器件,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如目的之一所述的有机化合物。
在一个实施方案中,所述有机薄膜层包括发光层,所述发光层包括作为主体材料的如目的之一所述的有机化合物。
本发明提供的OLED器件中,阳极材料可以为金属、金属氧化物或导电性聚合物;其中,所述金属包括铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金,所述金属氧化物包括氧化铟锡(ITO)、氧化铟锌(IZO)、氧化锌、氧化铟镓锌(IGZO)等,所述导电性聚合物包括聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除以上有助于空穴注入的材料及其组合,还包括已知的适合做阳极的材料。
所述OLED器件中,阴极材料可以为金属或多层金属材料;其中,所述金属包括铝、镁、银、铟、锡、钛等及它们的合金,所述多层金属材料包括LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合,还包括已知的适合做阴极的材料。
所述OLED器件中,有机薄膜层包括至少一层发光层(EML)和设置于发光层两侧的空穴注入层(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)或电子注入层(EIL)中的任意一种或至少两种的组合。除本发明目的之一所述的有机化合物之外,空穴/电子注入及传输层还可以为咔唑类化合物、芳胺类化合物、苯并咪唑类化合物及金属化合物等。所述OLED器件的阴极上(远离阳极的一侧)还可以任选地设置盖帽层(CPL)。
本发明所述OLED器件可以通过以下方法制备: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。其中,形成有机薄层可采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明的目的之四在于提供一种显示面板,所述显示面板包括如目的之三所述的OLED器件。
本发明的目的之五在于提供一种有机发光显示装置,包括如目的之四所述的显示面板。
本发明的目的之六在于提供一种一种电子设备,所述电子设备包括如目的之四所述的显示面板。
以下示例性地列举几种本发明所述有机化合物的制备实施例:
实施例1
化合物P1的合成:
(1)在250mL圆底烧瓶中将中间体P1-1(15mmol)、醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、二(三苯基膦)二氯化钯Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合,在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P1-2。
(2)在250mL圆底烧瓶中将中间体P1-2(10mmol)、化合物1,8-二碘萘(12mmol)和四(三苯基膦)钯Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P1-3。
(3)在250mL圆底烧瓶中将中间体P1-3(10mmol)、三乙胺Et3N(12mmol)和光气(30mmol溶于甲苯30mL)加入到干燥50mL甲苯中,在氮气氛围下0℃搅拌1h,然后将得到的混合物在室温下反应5h。加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P1-4。
(4)在250mL圆底烧瓶中将中间体P1-4(15mmol)、醋酸钯Pd(OAc)2(2mmol)、三苯基膦PPh3(4mmol)、降冰片烯NBE(15mmol)、CS2CO3(60mmol)与干燥的二氯乙烷(60mL),在95℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到化合物P1。
测试目标产物P1的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C29H17NO,计算值为395.1,测试值为395.0。
元素分析(JSL有机元素分析仪JM1000,型号:JM1000CN/HCN/TOC/CN):理论值C,88.08;H,4.33;N,3.54;测试值C,88.08;H,4.32;N,3.54。
实施例2
化合物P8的合成:
(1)在250mL圆底烧瓶中将中间体P8-1(15mmol)、醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、二(三苯基膦)二氯化钯Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合,在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P8-2。
(2)在250mL圆底烧瓶中将中间体P8-2(10mmol)、化合物1,8-二碘萘(12mmol)和四(三苯基膦)钯Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P8-3。
(3)在250mL圆底烧瓶中将中间体P8-3(10mmol)、Et3N(12mmol)和光气(30mmol溶于甲苯30mL)加入到干燥50mL甲苯中,在氮气氛围下0℃搅拌1h,然后将得到的混合物在室温下反应5h。加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P8-4。
(4)在250mL圆底烧瓶中将中间体P8-4(15mmol)、Pd(OAc)2(2mmol)、PPh3(4mmol)、NBE(15mmol)、CS2CO3(60mmol)与干燥的二氯乙烷(60mL),在95℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P8。
测试目标产物P8的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C34H20N2O,计算值为472.2,测试值为472.1。
元素分析:理论值C,86.42;H,4.27;N,5.93;测试值C,86.41;H,4.27;N,5.93。
实施例3
化合物P13的合成:
(1)在250mL圆底烧瓶中将中间体P13-1(15mmol)、醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、二(三苯基膦)二氯化钯Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合,在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P13-2。
(2)在250mL圆底烧瓶中将中间体P13-2(10mmol)、化合物1,8-二碘萘(12mmol)和四(三苯基膦)钯Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P13-3。
(3)在250mL圆底烧瓶中将中间体P13-3(10mmol)、Et3N(12mmol)和光气(30mmol溶于甲苯30mL)加入到干燥50mL甲苯中,在氮气氛围下0℃搅拌1h,然后将得到的混合物在室温下反应5h。加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P13-4。
(4)在250mL圆底烧瓶中将中间体P13-4(15mmol)、Pd(OAc)2(2mmol)、PPh3(4mmol)、NBE(15mmol)、CS2CO3(60mmol)与干燥的二氯乙烷(60mL),在95℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P13。
测试目标产物P1的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C28H16N2O,计算值为396.1,测试值为396.2。
元素分析:理论值C,84.83;H,4.07;N,7.07;测试值C,84.83;H,4.08;N,7.07。
实施例4
化合物P24的合成:
(1)将P24-1(0.5mmol)、P24-2(0.5mmol)、K2CO3(0.6mmol)、PdCl2(5×10-4mmol)、TPPDA(5×10-4mmol)加入邻二甲苯3mL溶液中混合,放入50mL的烧瓶中,在100℃下反应24小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P24-3。
(2)在250mL圆底烧瓶中将中间体P24-3(15mmol)、醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、二(三苯基膦)二氯化钯Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合,在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P24-4。
(3)在250mL圆底烧瓶中将中间体P24-4(10mmol)、化合物1,8-二碘萘(12mmol)和四(三苯基膦)钯Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P 24-5。
(4)在250mL圆底烧瓶中将中间体P24-5(10mmol)、Et3N(12mmol)和光气(30mmol溶于甲苯30mL)加入到干燥50mL甲苯中,在氮气氛围下0℃搅拌1h,然后将得到的混合物在室温下反应5h。加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P 24-6。
(5)在250mL圆底烧瓶中将中间体P24-6(15mmol)、Pd(OAc)2(2mmol)、PPh3(4mmol)、NBE(15mmol)、CS2CO3(60mmol)与干燥的二氯乙烷(60mL),在95℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P26。
测试目标产物P26的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C33H19N3O,计算值为473.2,测试值为473.1。
元素分析:理论值C,83.70;H,4.04;N,8.87;测试值C,83.70;H,4.05;N,8.87。
实施例5
化合物P29的合成:
(1)在250mL圆底烧瓶中将中间体P29-1(15mmol)、醋酸钾(40mmol)与干燥的1,4-二氧六环(60mL)、二(三苯基膦)二氯化钯Pd(PPh3)2Cl2(0.4mmol)和联硼酸频那醇酯(25mmol)混合,在90℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P29-2。
(2)在250mL圆底烧瓶中将中间体P29-2(10mmol)、P29-3(12mmol)和四(三苯基膦)钯Pd(PPh3)4(0.3mmol)加入到甲苯(30mL)/碳酸钾(12mmol)水溶液(10mL)的混合物中,在氮气氛围下回流反应12h。将得到的混合物冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P29-4。
(3)在250mL圆底烧瓶中将中间体P29-4(10mmol)、Et3N(12mmol)和光气(30mmol溶于甲苯30mL)加入到干燥50mL甲苯中,在氮气氛围下0℃搅拌1h,然后将得到的混合物在室温下反应5h。加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到目标产物P29-5。
(4)在250mL圆底烧瓶中将中间体P29-5(15mmol)、Pd(OAc)2(2mmol)、PPh3(4mmol)、NBE(15mmol)、CS2CO3(60mmol)与干燥的二氯乙烷(60mL),在95℃氮气氛围下搅拌48小时。得到的中间体冷却到室温,加入水中,然后通过硅藻土垫过滤,滤液用二氯甲烷萃取,然后用水洗涤,并采用无水硫酸镁干燥,过滤和蒸发后,用硅胶柱层析纯化粗产物得到中间体P29。
测试目标产物P29的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C35H29NO,计算值为479.2,测试值为479.1。
元素分析:理论值C,87.65;H,6.09;N,2.92;测试值C,87.65;H,6.10;N,2.92。
具体实施方式中所使用的本发明化合物的制备方法均与上述方法相似,不一一赘述,仅提供其表征结果,质谱分析与元素分析结果如表1所示。
对比例1:化合物CI;对比例2:化合物CII
表1
化合物能级的模拟计算
运用密度泛函理论(DFT),对各实施例和对比例的化合物进行能级的模拟计算。通过Gaussian 09程序包(Gaussian Inc.),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)模拟计算了化合物的最低单线态能级ES1和最低三线态能级ET1。结果如表2所示。
表2化学物能级模拟计算结果
从表2可以看出,本发明提供的化合物具有较合适的HUMO能级和LUMO能级,和较高的最低三线态能级ET1(例如>2.26eV),将该化合物适合用作红光主体材料,同时具有较深的LUMO能级(<1.67eV),能够促进电子的注入和提高发光效率。
应用例1
本应用例提供一种OLED器件(有机发光器件),如图1所示,包括依次层叠的基板1、阳极(ITO)2、空穴注入层3、第一空穴传输层41、第二空穴传输层42、发光层5、电子传输层6、电子注入层7、阴极8(镁银电极,镁银质量比91:19)和盖帽层9(CPL)。图中箭头表示出光方向。
上述OLED器件的具体制备步骤如下:
1)将带有氧化铟锡(ITO)阳极(厚度为15nm)的玻璃基板切成50mm×50mm×0.7mm的大小,分别在异丙醇和去离子水中超声处理30分钟,然后暴露在臭氧下约10min来进行清洁,将清洗后的玻璃基板安装到真空沉积设备上;
2)在ITO阳极层上,通过真空蒸镀方式共同蒸镀空穴注入层材料(化合物b)和p掺杂材料(化合物a),掺杂比例为3%(质量比);厚度为5nm,作为空穴注入层;
3)在空穴注入层上真空蒸镀空穴传输材料(化合物c),厚度为100nm,作为第一空穴传输层;
4)在第一空穴传输层上真空蒸镀空穴传输材料(化合物d),厚度为5nm,作为第二空穴传输层;
5)在第二空穴传输层上真空共同蒸镀发光主体材料化合物P1、化合物e(蒸镀的比例1:1)和掺杂材料化合物f,掺杂比例为3%(质量比),厚度为30nm,作为发光层;
6)在发光层上真空蒸镀化合物g,厚度为30nm,作为电子传输层;
7)在电子传输层上真空共同蒸镀化合物h和n掺杂材料(化合物i),掺杂质量比例为1:1;厚度为5nm,作为电子注入层;
8)在电子注入层上真空蒸镀镁银电极,其中,Mg:Ag质量比为1:9,厚度为10nm,作为阴极;
9)在阴极上真空蒸镀化合物j,厚度为100nm,作为盖帽层。
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流,然后用电流除以发光面积得到OLED器件在不同电压下的电流密度;用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度;根据OLED器件在不同电压下的电流密度和亮度,得到在相同电流密度(10mA/cm2)下的工作电压和电流效率CE(10mA/cm2)(cd/A),Von为亮度1cd/m2下的启亮电压;通过测量OLED器件的亮度达到初始亮度的95%时的时间而获得寿命LT95(在50mA/cm2测试条件下);测试数据如表3所示。
表3 OLED器件性能测试结果
由表3可知,本发明提供的显示面板由于采用本发明的化合物作为红光主体材料,具有较低的驱动电压、较高的发光效率和较长的使用寿命。例如,启亮电压可小于等于3.82V;电流效率CE(10mA/cm2)可大于等于38.0cd/A;寿命LT95可大于等于100h。相对于应用对比例1~2,本发明应用例1~16,提供的OLED器件的以上性能得到明显提升,这主要得益于本发明提供的有机化合物具有合适的HOMO能级、LUMO能级、以及较高的三线态能级,能提高电子注入能力,从而使得采用其作为红光主体材料的有机发光器件获得较低的驱动电压和较高的发光效率;同时本发明提供的有机化合物还具有良好的热稳定性和成膜性,有利于器件的稳定性,提升器件寿命。
申请人声明,本发明通过上述实施例来说明本发明的有机化合物及其应用,但本发明并不局限于上述实施例,即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (10)
1.一种有机化合物,其特征在于,所述有机化合物具有如下式I所示结构:
其中X1-X12各自独立选自N或者CRa,Ra为氢、C1-C10的烷基、C1-C10的环烷基、C6-C30的芳基、C3-C30的杂芳基、OR1或SR1;
R1为C1-C10的烷基;
L选自单键、亚苯基、亚联苯基或亚萘基;
n为1;
Ar选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的菲基、取代或未取代的芴基、取代或未取代的吡啶基或取代或未取代的三嗪基;
所述取代的苯基、取代的萘基、取代的菲基、取代的芴基、取代的吡啶基或取代的三嗪基中取代基为C1-C10的烷基或C6-C30的芳基。
2.根据权利要求1所述的有机化合物,其特征在于,X1-X12均为CRa,Ra为氢、C1-C10的烷基、C1-C10的环烷基、=C6-C30的芳基、C3-C30的杂芳基。
3.根据权利要求1所述的有机化合物,其特征在于,X1-X12中至少一者为N。
4.一种有机化合物,其特征在于,所述有机化合物为如下化合物中的任意一种:
其中D代表氘。
5.一种有机电致发光材料,其特征在于,所述有机电致发光材料包括如权利要求1-4中任一项所述的有机化合物。
6.一种OLED器件,其特征在于,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如权利要求1-4中任一项所述的有机化合物。
7.根据权利要求6所述的OLED器件,其特征在于,所述有机薄膜层包括发光层,所述发光层包括作为主体材料的如权利要求1-4中任一项所述的有机化合物。
8.一种显示面板,其特征在于,所述显示面板包括如权利要求6或7任一项所述的OLED器件。
9.一种有机发光显示装置,其特征在于,包括如权利要求8所述的显示面板。
10.一种电子设备,其特征在于,所述电子设备包括如权利要求8所述的显示面板。
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