CN115073477B - 一种咔唑类衍生物及其制备方法和光电器件 - Google Patents
一种咔唑类衍生物及其制备方法和光电器件 Download PDFInfo
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- CN115073477B CN115073477B CN202210502457.7A CN202210502457A CN115073477B CN 115073477 B CN115073477 B CN 115073477B CN 202210502457 A CN202210502457 A CN 202210502457A CN 115073477 B CN115073477 B CN 115073477B
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- carbazole derivative
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- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 9
- 239000012044 organic layer Substances 0.000 claims description 10
- 230000005693 optoelectronics Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 42
- 239000010410 layer Substances 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 24
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 238000005406 washing Methods 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 9
- 229910000024 caesium carbonate Inorganic materials 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 230000001376 precipitating effect Effects 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000005303 weighing Methods 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000434 field desorption mass spectrometry Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 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 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 241000985284 Leuciscus idus Species 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 229960003805 amantadine Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- -1 carbazole derivative compound Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000001308 synthesis method 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
- 229930192474 thiophene Natural products 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
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- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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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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- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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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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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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Abstract
本发明公开了一种咔唑衍生物及其制备方法,其结构如化学式1所示:
Description
技术领域
本发明涉及有机光电材料技术领域,更具体的说是涉及一种一种咔唑类衍生物及其制备方法和光电器件。
背景技术
有机电致发光技术作为最新一代显示技术,由其制备的光电器件由于有着功耗低、响应速度快、宽视角、高分辨率、宽温度特性、质量轻以及可卷曲等特点而逐渐被大众认可,有机电致发光显示技术与传统的LCD显示方式不同,无需背光灯,采用非常薄的有机材料涂层和玻璃基板,当有电流通过时,这些有机材料就会发光。近些年国际各大企业都在不断加强对OLED技术的研究,OLED技术得到了进一步的完善。
目前,有机发光器件的材料主要存在寿命短的技术问题,而且发光效率和功率效率低以及驱动电压高,造成该类材料的使用成本增加,后期的使用对于市场的发展存在很大的障碍。
因此,研发一种新的咔唑类衍生物从而制备驱动电压低、发光效率高,使用寿命长的有机电致发光器件是本领域人员亟需解决的技术问题。
发明内容
有鉴于此,本发明的目的在于提供一种咔唑类衍生物,作为有机电致发光器件的发光材料能够提高器件的发光效率,而且延长使用寿命,降低驱动电压。
为了实现上述目的,本发明采用如下技术方案:
一种咔唑衍生物,其结构如化学式1所示:
其中,式中:
R选自-L-(A)n或-CX1X2;
L选自单键、取代或未取代的C1~C30亚烷基、取代或未取代的C6~C30亚芳基、取代或未取代的3元~30元亚杂芳基、或取代或未取代的C3~C30亚环烷基;
A选自取代或未取代的C6~C30芳基、取代或未取代的3元~30元杂芳基、或-NX3X4;
X1至X4各自独立地选自氢、氘、卤素、氰基、取代或未取代的C1~C30烷基、取代或未取代的C6~C30的稠环、取代或未取代的C6~C30芳基、取代或未取代的3元~30元杂芳基、取代或未取代的C3~C30环烷基、取代或未取代的C3~C30杂环烷基;或,与相邻取代基连接形成一个或多个环;
n选自1或2,且当n选自为2,每个A可以相同或不同。
优选的,所述C3~C30环烷基为单环烷基、多环烷基、螺烷基中的任一种,且取代的C3~C30环烷基上的碳原子可被至少一个杂原子取代;所述杂原子为N、O、S、Si、Se、Ge中的至少一种;
所述C6~C30芳基为单环基团或多环基团;所述多环基团具有两个碳为两个邻接环共用的多个环,其中至少一个环是芳香族环,其它环为环烷基、环烯基、芳基、杂芳基中的至少一种。
优选的,所述芳基为单环芳基和多环芳基;所述多环芳基具有两个以上的环,其中两个碳为两个邻接环共用,所述环至少一个是芳基,其它环选自环烷基、环烯基、芳基、杂芳基中一种或多种的组合。
优选的,所述杂芳基为呋喃、噻吩、吡啶,三嗪中的任一种。
优选的,所述C1~C30烷基选自甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基中的任一种;
优选的,所述环烷基包括单环、多环、螺烷基;所述环烷基优选为C3~C30的环烷基,更具体地包括环丙基、环戊基、环己基、金刚烷胺基;
所述杂环烷基为至少含有一个杂原子的环烷基,所述杂环烷基优选为含有包括至少一个所述杂原子的3到7个环原子的杂环烷基,并且包括环胺,更具体地包括吗啉基、哌啶基、吡咯烷基、四氢呋喃、四氢吡喃,所述杂原子选自N、O、S、P、B、Si、Se、Ge中的一种或多种的组合;所述杂原子优选为N、O、S中一种或多种的组合。
所述杂原子为N、O、S中的至少一种。
所述所述C6~C30芳基选自苯、联苯、三联苯、萘、蒽、菲、芘中的任一种。
需要说明的是,上述的“取代”是指与化合物的碳原子键合的氢原子变成另外的取代基,并且取代的位置没有限制,只要该位置为氢原子被取代的位置即可,即取代基可以取代的位置,并且当两个或更多个取代基取代时,两个或更多个取代基可以彼此相同或不同。
优选的,所述R选自以下基团中的任一种:
上述为基团连接位置。
优选的,所述化学式1包括式F001~式F087中的任:
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本发明的另一个目的在于提供上述的咔唑类衍生物的制备方法,合成路线如下:
其中,X选自F、Cl、Br或I;
包括以下步骤:
在保护气氛下,称取化合物A,化合物B,碳酸铯放入反应体系中,接着往反应体系中加入二甲基亚砜和4-二甲氨基吡啶使反应体系在保护气氛下90℃~140℃反应20~30h,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷做溶剂,用硅胶柱层析,滤液浓缩固体析出,得到化学式1。
优选的,所述保护气氛均为氮气或氩气;
所述化合物A和化合物B的摩尔比为1:(1.05~1.3);更优选为1:1.1;
所述4-二甲氨基吡啶与化合物A的摩尔比为(0.01~0.1):1;更优选为0.05:1;
所述化合物A与二甲基亚砜的配比为4.3mmol:20~30mL。
本发明实施例的另一目的在于提供一种光电器件,该光电器件为有机电致发光器件,其包括第一电极、第二电极以及至少一层设置在所述第一电极和所述第二电极之间的有机物层,所述的有机物层包含上述的有机咔唑衍生物。
优选的,所述有机物层包括发光层;所述发光层包括所述咔唑衍生物和掺杂材料,掺杂材料采用在欧洲专利申请07102949.0的化合物作为发光层中的掺杂剂;
需要说明的是,有机物层还可包括空穴注入层、空穴传输层、空穴注入和空穴传输技能层的复合层、电子阻挡层、空穴阻挡层、电子传输层、电子注入层、电子传输层和电子注入技能层的复合层中的至少一层,且其中的至少一层可包含或不包含上述咔唑衍生物化合物,但不限于此。
另外,掺杂可以选择其他类型的有机化合物,并不只限于上述掺杂化合物;
优选的,所述有机咔唑衍生物与掺杂材料的质量比为(90~99.5):(0.5~10)。
经由上述的技术方案可知,与现有技术相比,本发明具有如下有益效果:本发明实施例提供的一种咔唑衍生物,将该咔唑衍生物用于有机电致发光器件等光电器件后,可降低光电器件的驱动电压、显著提高光电器件的发光效率以及延长光电器件的的使用寿命。另外,本发明实施例提供的咔唑衍生物制备方法,具有合成步骤简单、易提纯,且目标产物收率高的特点,适于推广与应用。
具体实施方式
下面对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
制备化合物F001,其具体步骤如下:
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其具体的制备方法包括以下步骤:
在氮气保护体系下,称取化合物S001(71.29mmol,20g),S002(78.42mmol,25.11g),无水碳酸钾(142.58mmol,19.7g)放入反应体系中,接着往反应体系中加入150ml甲苯溶液,150ml乙醇,75ml纯净水,随后加入四(三苯基膦)钯(2.14mmol,2.47g),加热90℃,搅拌均匀并反应24小时,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷和石油醚混合溶液做展开剂,用硅胶柱层析,滤液浓缩固体析出,得到R001(19.37g,产率:68.98%)。
在氮气保护体系下,称取化合物R001(50.78mmol,20g),碳酸铯(76.17mmol,24.82g)放入反应体系中,接着往反应体系中加入300mL二甲基亚砜,4-二甲氨基吡啶(1.27mmol,0.16g)使反应体系在氮气保护下140℃反应48小时,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷做溶剂,用硅胶柱层析,滤液浓缩固体析出,得到化合物M001(3.26g,产率:35.93%)。
在氮气保护体系下,称取化合物M001(27.98mmol,10g),B001(30.78mol,7.41g),碳酸铯(83.94mol,27.35g)放入反应体系中,接着往反应体系中加入300mL二甲基亚砜,4-二甲氨基吡啶(1.4mmol,0.17g)使反应体系在氮气保护下90℃反应24小时,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷做溶剂,用硅胶柱层析,滤液浓缩固体析出,得到咔唑衍生物F001(11.3g,产率:71.91%)。
HPLC纯度:大于99%;
质谱:计算值为561.2,测试值为561.65;
元素分析:
计算值C:83.40%;H:4.13%;N:12.47%;
测试值C:83.42%;H:4.11%;N:12.47%;
实施例2
制备化合物F005,其具体步骤如下:
在氮气保护体系下,称取化合物M001(27.98mmol,10g),B005(30.78mol,11.72g),碳酸铯(83.94mol,27.35g)放入反应体系中,接着往反应体系中加入300mL二甲基亚砜,4-二甲氨基吡啶(1.4mmol,0.17g)使反应体系在氮气保护下90℃反应24小时,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷做溶剂,用硅胶柱层析,滤液浓缩固体析出,得到咔唑衍生物F005(12.04g,产率:61.32%)。
HPLC纯度:大于99%;
质谱:计算值为701.22,测试值为701.79;
元素分析:
计算值C:83.86%;H:3.88%;N:9.98%;O:2.28%;
测试值C:83.84%;H:3.89%;N:9.98%;O:2.29%;
实施例3
制备化合物F011,其具体步骤如下:
在氮气保护体系下,称取化合物M001(27.98mmol,10g),B011(30.78mol,8.64g),碳酸铯(83.94mol,27.35g)放入反应体系中,接着往反应体系中加入300mL二甲基亚砜,4-二甲氨基吡啶(1.4mmol,0.17g)使反应体系在氮气保护下90℃反应24小时,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷做溶剂,用硅胶柱层析,滤液浓缩固体析出,得到咔唑衍生物F011(10.13g,产率:60.18%)。
HPLC纯度:大于99%;
质谱:计算值为601.19,测试值为601.67;
元素分析:
计算值C:81.85%;H:3.85%;N:11.64%;O:2.66%;
测试值C:81.84%;H:3.86%;N:11.65%;O:2.65%;
实施例4
制备化合物F013,其具体步骤如下:
在氮气保护体系下,称取化合物M001(27.98mmol,10g),B013(30.78mmol,8.24g),碳酸铯(83.94mmol,27.35g)放入反应体系中,接着往反应体系中加入300mL二甲基亚砜,4-二甲氨基吡啶(1.4mmol,0.17g)使反应体系在氮气保护下90℃反应24小时,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷做溶剂,用硅胶柱层析,滤液浓缩固体析出,得到咔唑衍生物F013(11.62g,产率:70.55%)。
HPLC纯度:大于99%;
质谱:计算值为588.21,测试值为588.67;
元素分析:
计算值C:81.61%;H:4.11%;N:14.28%;
测试值C:81.62%;H:4.10%;N:14.28%;
实施例5
制备化合物F014,其具体步骤如下:
在氮气保护体系下,称取化合物M001(27.98mmol,10g),B014(30.78mmol,8.55g),碳酸铯(83.94mmol,27.35g)放入反应体系中,接着往反应体系中加入300mL二甲基亚砜,4-二甲氨基吡啶(1.4mmol,0.17g)使反应体系在氮气保护下90℃反应24小时,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷做溶剂,用硅胶柱层析,滤液浓缩固体析出,得到咔唑衍生物F014(10.42g,产率:62.2%)。
HPLC纯度:大于99%;
质谱:计算值为598.27,测试值为598.74;
元素分析:
计算值C:80.24%;H:5.72%;N:14.04%;
测试值C:80.26%;H:5.71%;N:14.03%;
实施例6
制备化合物F019,其具体步骤如下:
在氮气保护体系下,称取化合物M001(27.98mmol,10g),B019(30.78mmol,12.92g),碳酸铯(83.94mmol,27.35g)放入反应体系中,接着往反应体系中加入300mL二甲基亚砜,4-二甲氨基吡啶(1.4mmol,0.17g)使反应体系在氮气保护下90℃反应24小时,反应停止后体系冷却至室温,有沉淀析出,将沉淀抽滤,用无水乙醇冲洗烘干,得到固体粉末,用二氯甲烷做溶剂,用硅胶柱层析,滤液浓缩固体析出,得到咔唑衍生物F019(11.63g,产率:56.11%)。
HPLC纯度:大于99%;
质谱:计算值为740.27,测试值为740.87;
元素分析:
计算值C:84.30%;H:4.35%;N:11.34%;
测试值C:84.33%;H:4.33%;N:11.33%;
实施例7-16
按照实施例1中的合成方法,仅将相应反应物替换,可以合成实施例7-16的目标化合物,其FD-MS(即质谱)的结果如表1所示。
表1实施例7-16的目标化合物的FD-MS的结果
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本发明还提供一种包含本发明化学式1所示的化合物的有机电致发光器件。
有机电致发光器件包括:第一电极、第二电极和置于所述两电极之间的一个或者更多个有机物层,其中,所述有机物层的一个或更多个层包含有本发明化学式1所示的化合物;本发明化学式1所示化合物可以是单一形态或与其它物质混合存在于有机物层中。
有机物层至少包括空穴注入层、空穴传输层、既具备空穴注入又具备空穴传输技能层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
器件实施例17利用发光化合物制备有机电致发光器件(OLED)
所制备OLED器件的结构为:ITO阳极/HIL/HTL/EML/HBL/ETL/EIL/阴极
a、ITO阳极:将涂层厚度为的ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,用甲醇、丙酮、异丙醇依次超声波洗涤(每次洗涤5min),干燥,然后转移至等离子体清洗机内洗涤5min,再送至蒸镀机中,以该基板为阳极,在其上依次蒸镀其它功能层。
b、HIL(空穴注入层):真空蒸镀2-TNATA(即N1-(2-萘基)-N4,N4-二(4-(2-萘基(苯基)氨基)苯基)-N1-苯基苯-1,4-二胺)形成空穴注入层。
c、HTL(空穴传输层):真空蒸镀NPB(即N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺)形成空穴传输层。
d、EML(发光层):主体材料采用如下结构所示RH,掺杂材料E,作为发光层中的掺杂剂,以重量比90:10混合蒸镀形成发光层。/>
e、HBL(空穴阻挡层):真空蒸镀BAlq形成空穴阻挡层。
f、ETL(电子传输层):真空蒸镀Alq3形成电子传输层。
g、EIL(电子注入层):真空蒸镀LiF形成电子注入层。
h、阴极:蒸镀Al形成阴极,得到OLED器件。
参照上述方法,将RH分别替换为F001、F005、F009、F011、F013、F014、F017、F019、F023、F027、F029、F032、F039、F050、F062、F083,制备得到相应化合物的有机电致发光器件。
器件实施例17-33
对器件实施例17-33中得到的OLED器件进行发光性能检测,采用KEITHLEY 2400型测量单元,CS-2000分光辐射亮度计,测试驱动电压、发光寿命及发光效率。测试结果参见表2。
表2实施例17-33中有机电致发光器件检测结果
化合物 | 驱动电压(V) | 亮度(cd/cm2) | 效率(cd/A) | 寿命T(95) |
RH | 6.0 | 5000 | 23.0 | 59.2 |
F001 | 4.15 | 5000 | 41.3 | 229 |
F005 | 3.77 | 5000 | 39.4 | 303 |
F009 | 3.49 | 5000 | 40.8 | 283 |
F011 | 4.01 | 5000 | 38.7 | 291 |
F013 | 3.62 | 5000 | 42.5 | 297 |
F014 | 4.11 | 5000 | 39.6 | 279 |
F017 | 3.81 | 5000 | 41.8 | 301 |
F019 | 3.52 | 5000 | 37.2 | 308 |
F023 | 3.88 | 5000 | 40.7 | 293 |
F027 | 4.05 | 5000 | 39.1 | 312 |
F029 | 3.92 | 5000 | 40.6 | 294 |
F032 | 4.22 | 5000 | 39.1 | 304 |
F039 | 4.61 | 5000 | 41.5 | 274 |
F050 | 3.84 | 5000 | 36.2 | 282 |
F062 | 4.37 | 5000 | 42.6 | 263 |
F083 | 3.96 | 5000 | 38.5 | 306 |
由表2可以看出,在发光亮度均为5000cd/cm2,与对比例17相比,本发明提供的器件的驱动电压明显小于对比例17的驱动电压,而效率及寿命远高于对比例17。由此可知,使用本发明提供的化合物作为发光层材料所制备的有机电致发光器件与使用比较化合物RH作为发光层材料所制备的有机电致发光器件相比,驱动电明显降低,发光效率以及寿命得到显著提高。
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。对于实施例公开的装置而言,由于其与实施例公开的方法相对应,所以描述的比较简单,相关之处参见方法部分说明即可。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (2)
1.一种咔唑衍生物,其特征在于,所述咔唑衍生物包括以下结构:
2.一种光电器件,其特征在于,所述光电器件为有机电致发光器件,所述有机电致发光器件包括第一电极、第二电极以及至少一层设置在所述第一电极和所述第二电极之间的有机物层,所述的有机物层包含权利要求1所述的咔唑衍生物。
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