CN117229198A - 一种有机电致发光化合物及其制备方法与应用 - Google Patents
一种有机电致发光化合物及其制备方法与应用 Download PDFInfo
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- CN117229198A CN117229198A CN202311194274.4A CN202311194274A CN117229198A CN 117229198 A CN117229198 A CN 117229198A CN 202311194274 A CN202311194274 A CN 202311194274A CN 117229198 A CN117229198 A CN 117229198A
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- organic electroluminescent
- electroluminescent compound
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 11
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000005525 hole transport Effects 0.000 abstract description 14
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 10
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- 239000012043 crude product Substances 0.000 description 8
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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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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
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- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 101100391172 Dictyostelium discoideum forA gene Proteins 0.000 description 1
- 101100391182 Dictyostelium discoideum forI gene Proteins 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- -1 aromatic diamine small molecule Chemical class 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
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- GHQCIALFYKYZGS-UHFFFAOYSA-N dibenzofuran-3-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3OC2=C1 GHQCIALFYKYZGS-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 239000010408 film Substances 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 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
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 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 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical group C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
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- 238000002061 vacuum sublimation Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
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- 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
- C07D405/12—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 chain containing hetero atoms as chain links
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- 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
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- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明涉及有机电致发光材料技术领域,尤其涉及一种有机电致发光化合物及其制备方法与应用;所述有机电致发光化合物具有如式I所示结构,通过分子结构和取代基的设计赋予了所述有机电致发光化合物较高的玻璃化转变温度和良好的热稳定性,避免其在高温沉积工艺中的降解;并且显著提升了其作为空穴传输层的空穴传输性能以及稳定性,使包含其的OLED器件具有高发光效率和长工作寿命,改善了功率效率和功率消耗。
Description
本申请是申请日为2020年12月14日、申请号为202011475226.9、发明名称为“一种有机电致发光化合物及其制备方法与应用”的专利的分案申请。
技术领域
本发明涉及有机电致发光材料技术领域,尤其涉及一种有机电致发光化合物及其制备方法与应用。
背景技术
电致发光装置(EL装置)为自发光装置,其优点在于具有较宽的视角、较大的对比率和较快的响应时间。目前,第一个有机EL装置由伊士曼柯达(Eastman Kodak)通过使用芳香族二胺小分子和金属铝络合物作为用于形成发光层的材料[《应用物理学报(Appl.Phys.Lett.)》51,913,1987]。
现有技术中,通常在空穴传输层或空穴注入层以及激子阻挡层中使用空穴传输材料,常用的空穴传输材料为三芳胺衍生物,其含有至少两个三芳基胺基团或至少一个三芳基胺基团和至少一个咔唑基团;上述化合物通常来源于二芳基氨基取代基的三苯胺(TPA型)、二芳基氨基取代的联苯衍生物(TAD型)或这些基础化合物的组合。将上述化合物用于荧光OLED或磷光OLED,特别是在用于有机电致发光器件时,工作电压、效率、寿命以及升华期间的热稳定性方面,均需要改进。
有鉴于此,特提出本发明。
发明内容
针对现有技术存在的不足,本发明提供一种有机电致发光化合物及其制备方法与应用。
作为本发明的第一目的,提供一种有机电致发光化合物中间体;该中间体可用于合成有机电致发光化合物。
具体而言,所述有机电致发光化合物具有如式M-1所示结构:
作为本发明的第二目的,提供上述有机电致发光化合物中间体的制备方法,合成路线如下:
具体包括如下步骤:
(1)以化合物IM-01为原料,与邻硝基苯硼酸在催化剂作用下通过偶联反应,得到化合物IM-02;
(2)将化合物IM-02在催化剂作用下经闭环反应,得到具有如式M-1所示结构的所述有机电致发光化合物中间体;
作为优选,步骤(1)中,所述催化剂为钯催化剂;
作为优选,步骤(2)中,所述催化剂为膦催化剂;
进一步地,步骤(1)中,所述催化剂为四三苯基膦钯;
进一步地,步骤(2)中,所述催化剂为三苯基膦。
采用上述钯催化剂更有利于闭环反应的进行,提高有机电致发光化合物中间体的合成效率。
作为本发明的第三目的,提供一种有机电致发光化合物;该有机电致发光化合物具有良好空穴传输性能以及稳定性,可用于制造工作寿命较高的OLED器件。
具体而言,所述有机电致发光化合物具有如式I所示结构:
其中,Ar1、Ar2、Ar3各自独立的代表具有C6~C60的芳香族或C6~C60的杂芳香族环系。
作为优选,Ar1、Ar2、Ar3各自独立的代表苯、联苯、萘、菲、芴、螺二芴、二苯并呋喃或二苯并噻吩。
作为优选,所述有机电致发光化合物选自式H1~式H20中的一种或多种:
作为本发明的第四目的,提供上述有机电致发光化合物的制备方法,包括如下步骤:
(1)以为原料,与Ar1-X在催化剂作用下进行偶联反应,得到
(2)以为原料,与/>在催化剂作用下进行偶联反应,得到
其中,X代表卤素;
Ar1、Ar2、Ar3各自独立地具有与权利要求3相同的限定范围。
作为优选,步骤(1)中,所述催化剂为铜催化剂;优选为碘化亚铜;
作为优选,步骤(2)中,所述催化剂为钯催化剂;优选为Pd2(dba)3;
作为优选,X代表I。
作为本发明的第五目的,提供一种OLED器件用空穴传输层,所述空穴传输层包括上述的有机电致发光化合物。
作为本发明的第六目的,提供一种OLED器件,所述OLED器件包括阳极、阴极以及位于所述阳极和所述阴极之间的至少一层有机薄膜层;所述有机薄膜层包括空穴传输层,以及空穴注入层、电子阻挡层、空穴阻挡层、发光层、电子传输层、电子注入层中的任意一种或至少两种的组合;
所述空穴传输层为如上所述的OLED器件用空穴传输层。
作为本发明的第七目的,提供一种电子设备,所述电子设备包括如上所述的OLED器件。
本发明的优异效果:
(1)本发明提供的有机电致发光化合物具有稠环结构,通过分子结构和取代基的设计赋予了所述有机电致发光化合物较高的玻璃化转变温度和良好的热稳定性,避免其在高温沉积工艺中的降解;并且显著提升了其作为空穴传输层的空穴传输性能以及稳定性,使包含其的OLED器件具有高发光效率和长工作寿命,改善了功率效率和功率消耗。
(2)本发明所述的有机电致发光化合物适用于荧光OLED器件和磷光OLED器件,尤其适用于磷光OLED器件。
具体实施方式
以下实施例用于说明本发明,但不用来限制本发明的范围。
所涉及的化合物结构如下:
实施例1
本实施例提供一种有机电致发光化合物中间体M-1,结构如下:
所述M-1的合成路线如下:
具体包括如下步骤:
(1)合成IM-02:
向1000ml三口瓶中,加入2,7-二溴-9,9'-螺二芴(47.4g、0.1mol)和邻硝基苯硼酸(16.7g、0.1mol),加入甲苯250ml、乙醇125ml、水125ml,搅拌下加入碳酸钠(13.8g、0.13mol),再加入四三苯基膦钯(0.12g、0.00001mol),置换氮气,开始加热,缓缓升温至80℃(反应过程保持氮气保护),反应2小时,HPLC检测(原料2,7-二溴-9,9'-螺二芴<1%)、停止反应,降温至室温。反应结束后,冷却至25℃,分液,有机相加入无水硫酸钠干燥;柱层析,用甲苯作为洗脱剂;浓缩,得到粗品,用甲苯:乙醇=1:2重结晶,得到产品36.1g中间体IM-02,纯度>98%,收率70%。
(2)合成M-1:
向1000ml三口瓶中,加入IM-02(36.1g、0.07mol),加入二氯苯(500ml),加入三苯基膦(36.7g、0.14mol),置换氮气,缓缓升温至170℃,反应10小时,HPLC检测(IM-02<1%)、停止反应。减压将溶剂蒸出,降温至室温,加入乙酸乙酯溶解,柱层析分离,洗脱剂为石油醚乙酸乙酯,得到固体粗品,用甲苯:乙醇=1:4重结晶,得到产品23.7g中间体M-1,纯度98%,收率70%。
实施例2
本实施例提供一种有机电致发光化合物H1,结构如下:
所述H1的制备方法包括如下步骤:
(1)合成M-1-1:
向500ml三口瓶中,加入M-1(23.7g、0.049mol)和碘苯(10g、0.049mol),加入DMF200ml,搅拌下加入氢氧化钾(5.4g、0.098mol)、碘化亚铜(9.3g、0.049mol),加热至150℃反应3小时,HPLC检测(M-1<1%)、停止反应,将反应液降温,加入200ml水,有固体析出,过滤,得到粗品,用甲苯重结晶,得到22g中间体M-1-1,纯度98%,收率80%。
(2)合成H1:
向250ml三口瓶中,加入M-1-1(5.6g、0.01mol)和二(4-联苯基)胺(3.2g、0.01mol),加入甲苯100ml,搅拌下加入叔丁醇钠(1.2g、0.013mol)、Pd2(dba)3(0.046g、0.00005mol),置换氮气,加入三叔丁基膦10%甲苯溶液0.2g,开始加热,缓缓升温至80℃(反应过程保持氮气保护),反应2小时,HPLC检测(M-1-1<1%)、停止反应,降温至室温。反应结束后,冷却至25℃,食盐水洗2次,有机相加入无水硫酸钠干燥;柱层析,用甲苯作为洗脱剂;浓缩,得到粗品,用甲苯重结晶,得到产品6.4g产品H1,纯度>99%,收率80%。
对H1化合物进行了核磁检测,数据解析如下:
1HNMR(300MHz,CDCl3)δ8.55(d,1H),δ8.22(s,1H)δ8.20(d,1H),δ7.94~7.89(m,3H),δ7.75~7.73(m,5H),δ7.62~7.28(m,28H),δ7.16(t,1H)。
实施例3
本实施例提供一种有机电致发光化合物H2,结构如下:
所述H2的制备方法包括如下步骤:
(1)合成M-1-1:
同实施例2。
(2)合成H2:
向250ml三口瓶中,加入M-1-1(5.6g、0.01mol)和N-[1,1'-联苯-4-基]-9,9-二甲基-9H-芴-2-胺(3.6g、0.01mol),加入甲苯100ml,搅拌下加入叔丁醇钠(1.2g、0.013mol)、Pd2(dba)3(0.046g、0.00005mol),置换氮气,加入三叔丁基膦10%甲苯溶液0.2g,开始加热,缓缓升温至80℃(反应过程保持氮气保护),反应2小时,HPLC检测(M-1-1<1%)、停止反应,降温至室温。反应结束后,冷却至25℃,食盐水洗2次,有机相加入无水硫酸钠干燥;柱层析,用甲苯作为洗脱剂;浓缩,得到粗品,用甲苯重结晶,得到产品6.7g产品H2,纯度>99%,收率80%。
对H2化合物进行了核磁检测,数据解析如下:
1HNMR(300MHz,CDCl3)δ8.55(d,1H),δ8.22(s,1H)δ8.20(d,1H),δ7.94~7.86(m,5H),δ7.75~7.73(m,3H),δ7.62~7.28(m,25H),δ7.16(m,2H),δ1.69(s,6H)。
实施例4
本实施例提供一种有机电致发光化合物H5,结构如下:
所述H5的制备方法包括如下步骤:
(1)合成M-1-1:
同实施例2。
(2)合成H5:
向50ml三口瓶中,加入M-1-1(5.6g、0.01mol)和N-[1,1'-联苯-4-基]-二苯并[b,d]噻吩-3-胺(3.5g、0.01mol),加入甲苯100ml,搅拌下加入叔丁醇钠(1.2g、0.013mol)、Pd2(dba)3(0.046g、0.00005mol),置换氮气,加入三叔丁基膦10%甲苯溶液0.2g,开始加热,缓缓升温至80℃(反应过程保持氮气保护),反应2小时,HPLC检测(M-1-1<1%)、停止反应,降温至室温。反应结束后,冷却至25℃,食盐水洗2次,有机相加入无水硫酸钠干燥;柱层析,用甲苯作为洗脱剂;浓缩,得到粗品,用甲苯重结晶,得到产品6.6g产品H5,纯度>99%,收率80%。
对H5化合物进行了核磁检测,数据解析如下:
1HNMR(300MHz,CDCl3)δ8.55(d,1H),δ8.45(d,1H),δ8.22(s,1H)δ8.20(d,1H),δ8.01(d,1H),δ7.94~7.89(m,4H),δ7.75~7.73(m,3H),δ7.62~7.28(m,25H),δ7.16(t,1H)。
实施例5
本实施例提供一种有机电致发光化合物H8,结构如下:
所述H8的制备方法包括如下步骤:
(1)合成M-1-1:
同实施例2。
(2)合成H8:
向250ml三口瓶中,加入M-1-1(5.6g、0.01mol)和N-(二苯并[b,d]噻吩-3基)二苯并[b,d]呋喃-3-胺(3.65g、0.01mol),加入甲苯100ml,搅拌下加入叔丁醇钠(1.2g、0.013mol)、Pd2(dba)3(0.046g、0.00005mol),置换氮气,加入三叔丁基膦10%甲苯溶液0.2g,开始加热,缓缓升温至80℃(反应过程保持氮气保护),反应2小时,HPLC检测(M-1-1<1%)、停止反应,降温至室温。反应结束后,冷却至25℃,食盐水洗2次,有机相加入无水硫酸钠干燥;柱层析,用甲苯作为洗脱剂;浓缩,得到粗品,用甲苯重结晶,得到产品6.6g产品H8,纯度>99%,收率:80%。
对H8化合物进行了核磁检测,数据解析如下:
1HNMR(300MHz,CDCl3)δ8.55(d,1H),δ8.22(s,1H)δ8.20(d,1H),δ8.01~7.80(m,9H),δ7.73(s,1H),δ7.62~7.28(m,20H),δ7.16(t,1H),δ6.91(d,2H)。
实施例6
本实施例提供一种有机电致发光化合物H17,结构如下:
所述H17的制备方法包括如下步骤:
(1)合成M-1-1:
同实施例2。
(2)合成H17:
向250ml三口瓶中,加入M-1-1(5.6g、0.01mol)和N-[1,1'-联苯-2-基]-二苯并[b,d]噻吩-3-胺(3.5g、0.01mol),加入甲苯100ml,搅拌下加入叔丁醇钠(1.2g、0.013mol)、Pd2(dba)3(0.046g、0.00005mol),置换氮气,加入三叔丁基膦10%甲苯溶液0.2g,开始加热,缓缓升温至80℃(反应过程保持氮气保护),反应2小时,HPLC检测(M-1-1<1%)、停止反应,降温至室温。反应结束后,冷却至25℃,食盐水洗2次,有机相加入无水硫酸钠干燥;柱层析,用甲苯作为洗脱剂;浓缩,得到粗品,用甲苯重结晶,得到产品6.6g产品H17,纯度>99%,收率80%。
对H17化合物进行了核磁检测,数据解析如下:
1HNMR(300MHz,CDCl3)δ8.55(d,1H),δ8.45(d,1H),δ8.22(s,1H)δ8.20(d,1H),δ8.10(d,1H),δ8.01(d,1H),δ7.94~7.89(m,4H),δ7.73(s,1H),δ7.62~7.27(m,23H),δ7.35~7.08(m,4H)。
应用例1
本应用例提供一种OLED器件,所述OLED器件的制备方法如下:
(1)用三氯乙烯、丙酮、乙醇和蒸馏水依次对用于有机发光二极管(OLED)器件的玻璃基材上的透明电极氧化铟锡(ITO)薄膜(15Ω/sq,韩国三星康宁公司Samsung Corning)进行超声清洗,然后储存在异丙醇中;将ITO基材安装在真空气相沉积设备的基材夹具上。
(2)将化合物HIL引入真空气相沉积设备的室中,然后对所述设备的室压进行控制以达到10-6托,向室内施加电流以蒸发上述引入的物质,从而在ITO基材上形成厚度为60nm的空穴注入层。
(3)将本发明提供的有机电致化合物H1引入真空气相沉积设备的另一个室中,通过向该室施加电流以进行蒸发,从而在所述空穴注入层上形成厚度为20nm的空穴传输层。
(4)将化合物CBP引入真空气相沉积设备的一个室中作为基质材料,并将化合物D-1引入另一个室中作为掺杂剂;将两种材料以不同的速率进行蒸发,并以15重量%(以基质材料和掺杂剂的总重量为基准计)的掺杂量进行沉积,从而在空穴传输层上形成厚度为30nm的发光层。
(5)将化合物ETL引入一个室中,并将8-羟基喹啉合锂(lithium quinolate)引入另一个室中;将两种材料以相同的速率进行蒸发,并分别以50重量%的掺杂量进行沉积,从而在发光层上形成厚度为30nm的电子传输层。
(6)在电子传输层上沉积了厚度为2nm的8-羟基喹啉合锂作为电子注入层EIL。
(7)通过另一真空气相沉积设备在电子注入层上沉积厚度为150nm的Al阴极;得到所述OLED器件。
上述制备OLED器件所用的所有材料,在使用前通过在10-6托条件下的真空升华进行纯化。
应用例2
本应用例提供一种OLED器件,与应用例1的区别在于:将步骤(3)中的H1替换为H2。
应用例3
本应用例提供一种OLED器件,与应用例1的区别在于:将步骤(3)中的H1替换为H4。
应用例4
本应用例提供一种OLED器件,与应用例1的区别在于:将步骤(3)中的H1替换为H5。
应用例5
本应用例提供一种OLED器件,与应用例1的区别在于:将步骤(3)中的H1替换为H7。
应用例6
本应用例提供一种OLED器件,与应用例1的区别在于:将步骤(3)中的H1替换为H8。
应用例7
本应用例提供一种OLED器件,与应用例1的区别在于:将步骤(3)中的H1替换为H13。
应用例8
本应用例提供一种OLED器件,与应用例1的区别在于:将步骤(3)中的H1替换为H20。
对比例1
本对比例提供一种OLED器件,与应用例1的区别在于:将步骤(3)中的H1替换为HTL。
OLED器件的性能测试
使用杭州远方生产的OLED-1000多通道加速老化寿命与光色性能分析系统测试应用例1~8、对比例1提供的OLED器件的驱动电压、电流效率和寿命LT90;其中,LT90是指保持电流密度不变,亮度降至原始亮度90%所需要的时间。
具体测试结果如表1所示:
表1
由表1可知,与现有技术中的有机电致发光化合物相比,本发明的有机电致发光化合物具有优异的性质,因而本发明提供的有机电致发光器件具有高发光效率和长工作寿命;并且,该有机电致发光器件需要低驱动电压,从而改善了功率效率和功率消耗。
虽然,上文中已经用一般性说明、具体实施方式及试验,对本发明作了详尽的描述,但在本发明基础上,可以对之作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。
Claims (10)
1.一种有机电致发光化合物中间产物,其特征在于,具有如下结构:
其中,Ar1选自具有C6~C60的芳香族或C6~C60的杂芳香族环系。
2.根据权利要求1所述的有机电致发光化合物中间产物,其特征在于,Ar1选自苯、联苯、萘、菲、芴、螺二芴、二苯并呋喃或二苯并噻吩。
3.根据权利要求1所述的有机电致发光化合物中间产物,其特征在于,Ar1选自苯。
4.一种有机电致发光化合物中间体,其特征在于,具有如式M-1所示结构:
5.权利要求1-3任一项所述有机电致发光化合物中间产物或权利要求4所述的有机电致发光化合物中间体在制备式I所示结构的有机电致发光化合物中的应用:
其中,Ar1、Ar2、Ar3各自独立的代表具有C6~C60的芳香族或C6~C60的杂芳香族环系。
6.根据权利要求5所述的应用,其特征在于,Ar1、Ar2、Ar3各自独立的代表苯、联苯、萘、菲、芴、螺二芴、二苯并呋喃或二苯并噻吩。
7.根据权利要求5或6所述的应用,其特征在于,所述有机电致发光化合物选自式H1~式H20中的一种:
8.根据权利要求5~7任一项所述的应用,其特征在于,所述有机电致发光化合物的制备方法包括:
(1)与Ar1-X在碘化亚铜作用下进行偶联反应,得到/>
(2)与/>在Pd2(dba)3作用下进行偶联反应,得到/>
其中,X代表卤素;
Ar1、Ar2、Ar3各自独立地具有与权利要求5相同的限定范围。
9.一种有机电致发光化合物,其特征在于,具有式I所示结构:
其中,Ar1为苯、联苯;Ar2、Ar3各自独立的代表联苯、芴、螺二芴、二苯并呋喃或二苯并噻吩。
10.根据权利要求9所述的有机电致发光化合物,其特征在于,所述有机电致发光化合物为式H1所述的化合物:
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