WO2024087586A1 - 有机化合物及包含其的电子元件和电子装置 - Google Patents
有机化合物及包含其的电子元件和电子装置 Download PDFInfo
- Publication number
- WO2024087586A1 WO2024087586A1 PCT/CN2023/094055 CN2023094055W WO2024087586A1 WO 2024087586 A1 WO2024087586 A1 WO 2024087586A1 CN 2023094055 W CN2023094055 W CN 2023094055W WO 2024087586 A1 WO2024087586 A1 WO 2024087586A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- substituted
- unsubstituted
- carbon atoms
- independently selected
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 38
- 239000010410 layer Substances 0.000 claims description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims description 76
- 125000001424 substituent group Chemical group 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 48
- -1 spirobifluorenyl group Chemical group 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 230000005525 hole transport Effects 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000002346 layers by function Substances 0.000 claims description 13
- 239000004305 biphenyl Substances 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000000463 material Substances 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000007935 neutral effect Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 101000801088 Homo sapiens Transmembrane protein 201 Proteins 0.000 description 7
- 102100033708 Transmembrane protein 201 Human genes 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 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 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- HYCYKHYFIWHGEX-UHFFFAOYSA-N (2-phenylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=CC=C1 HYCYKHYFIWHGEX-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000012512 characterization method Methods 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
- 230000008020 evaporation Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- FCPAQNZCCWBDSY-UHFFFAOYSA-N 2-chloro-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(Cl)C=C3CC2=C1 FCPAQNZCCWBDSY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 101001121408 Homo sapiens L-amino-acid oxidase Proteins 0.000 description 2
- 102100026388 L-amino-acid oxidase Human genes 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 101100075910 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) IMA4 gene Proteins 0.000 description 2
- 101100233916 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) KAR5 gene Proteins 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011365 complex material Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000004431 deuterium atom Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 1
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- YFPRGLHBYSNHMW-UHFFFAOYSA-N 9h-fluoren-9-yl(trimethyl)silane Chemical compound C1=CC=C2C([Si](C)(C)C)C3=CC=CC=C3C2=C1 YFPRGLHBYSNHMW-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 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 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 101100012902 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) FIG2 gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- LCCGSMWCUQMFQF-UHFFFAOYSA-N [2-(4-chlorophenyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=C(Cl)C=C1 LCCGSMWCUQMFQF-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 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
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000005560 phenanthrenylene group Chemical group 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- 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
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/80—Constructional details
- H10K30/84—Layers having high charge carrier mobility
- H10K30/86—Layers having high hole mobility, e.g. hole-transporting layers or electron-blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
-
- 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
Definitions
- the present application belongs to the technical field of organic materials, and in particular, relates to an organic compound and an electronic component and an electronic device containing the organic compound.
- Organic electroluminescent devices are devices made by depositing a layer of organic material between two metal electrodes by spin coating or vacuum evaporation.
- the classic three-layer organic electroluminescent device includes a hole transport layer, an organic light-emitting layer, and an electron transport layer. The holes generated by the anode pass through the hole transport layer and the electrons generated by the cathode pass through the electron transport layer to combine in the organic light-emitting layer to form excitons, and then emit light.
- Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of the organic light-emitting layer as needed.
- OLED display technology has many advantages such as self-luminescence, no radiation, light weight, thin thickness, wide viewing angle, wide color gamut, stable color, fast response speed, strong environmental adaptability, and flexible display. Therefore, OLED display technology has received more and more attention and corresponding technical investment.
- Aromatic amine compounds can be used as hole transport materials in hole transport layers.
- monoamine derivatives substituted with heteroaromatic rings at the 9-position of the fluorene group have been reported as useful materials for improving the lifetime of OLED devices.
- the purpose of the present application is to provide an organic compound and an electronic component and an electronic device containing the organic compound, wherein the organic compound can improve the performance of the electronic component and the electronic device.
- the first aspect of the present application provides an organic compound having a structure shown in Formula 1:
- n and m are the same or different and are each independently selected from 1, 2 or 3;
- R 1 , R 2 , R 3 and R 4 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms or a trialkylsilyl group having 3 to 12 carbon atoms;
- n 1 represents the number of R 1 , and n 1 is selected from 0, 1, 2, 3 or 4. When n 1 is greater than 1, any two R 1 are the same or different;
- n 2 represents the number of R 2 , and n 2 is selected from 0, 1, 2, 3 or 4. When n 2 is greater than 1, any two R 2 are the same or different;
- n 3 represents the number of R 3 , and n 3 is selected from 0, 1, 2, 3 or 4. When n 3 is greater than 1, any two R 3 are the same or different;
- n 4 represents the number of R 4 , and n 4 is selected from 0, 1, 2, 3 or 4. When n 4 is greater than 1, any two R 4 are the same or different;
- A, B, C and D are the same or different and are independently selected from hydrogen or a group shown in Formula 2, and at least one of A, B, C and D is a group shown in Formula 2;
- a represents the number of L, and a is selected from 1 or 2;
- Ar1 and Ar2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a a substituted or unsubstituted heteroaryl group;
- L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
- the substituents in Ar 1 , Ar 2 , L, L 1 and L 2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar 1 form a saturated or unsaturated 3 to 15-membered ring; optionally, any two adjacent substituents in Ar 2 form a saturated or unsaturated 3 to 15-membered ring.
- the organic compound of the present application is a triarylamine compound with a multi-spirocyclic structure.
- This multi-spirocyclic structure can improve the carrier mobility of the molecule and increase the twisting degree of the molecule, which can effectively avoid stacking between the fluorene planes and inhibit molecular crystallization, thereby improving the film-forming property of the molecule; at the same time, this structure is also beneficial to increase the glass transition temperature of the molecule, improve the evaporation stability of the material, and improve the life of the device.
- a second aspect of the present application provides an electronic component, comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the above-mentioned organic compound.
- a third aspect of the present application provides an electronic device, comprising the electronic component described in the second aspect.
- FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to an embodiment of the present application.
- FIG. 2 is a schematic diagram of a first electronic device according to an embodiment of the present application.
- FIG3 is a schematic diagram of the structure of a photoelectric conversion device according to an embodiment of the present application.
- FIG. 4 is a schematic diagram of a second electronic device according to an embodiment of the present application.
- the present application provides an organic compound having a structure shown in Formula 1:
- n and m are the same or different and are each independently selected from 1, 2 or 3;
- R 1 , R 2 , R 3 and R 4 are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms or a trialkylsilyl group having 3 to 12 carbon atoms;
- n 1 represents the number of R 1 , and n 1 is selected from 0, 1, 2, 3 or 4. When n 1 is greater than 1, any two R 1 are the same or different;
- n 2 represents the number of R 2 , and n 2 is selected from 0, 1, 2, 3 or 4. When n 2 is greater than 1, any two R 2 are the same or different;
- n 3 represents the number of R 3 , and n 3 is selected from 0, 1, 2, 3 or 4. When n 3 is greater than 1, any two R 3 are the same or different;
- n 4 represents the number of R 4 , and n 4 is selected from 0, 1, 2, 3 or 4. When n 4 is greater than 1, any two R 4 are the same or different; A, B, C and D are the same or different, and are independently selected from hydrogen or a group shown in Formula 2, and at least one of A, B, C and D is a group shown in Formula 2;
- Ar 1 and Ar 2 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
- L, L1 and L2 are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
- the substituents in Ar 1 , Ar 2 , L, L 1 and L 2 are the same or different and are independently selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; optionally, any two adjacent substituents in Ar 1 form a saturated or unsaturated 3 to 15-membered ring; optionally, any two adjacent substituents in Ar 2 form a saturated or unsaturated 3 to 15-membered ring.
- any two adjacent substituents ⁇ form a ring means that the two substituents can form a ring but do not have to form a ring, including: the situation where two adjacent substituents form a ring and the situation where two adjacent substituents do not form a ring.
- any two adjacent substituents in Ar 2 form a saturated or unsaturated 3-15 membered ring
- any two adjacent substituents in Ar 2 can be connected to each other to form a saturated or unsaturated 3-15 membered ring, or any two adjacent substituents in Ar 2 can also exist independently.
- Any two adjacent substituents may include two substituents on the same atom, or one substituent each on two adjacent atoms; wherein, when there are two substituents on the same atom, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly connected; when there is one substituent each on two adjacent atoms, the two substituents may be fused into a ring.
- the fluorenyl group may be substituted by 1 or 2 or more substituents.
- the fluorenyl group may be: etc., but not limited thereto.
- each... is independently” and “... are independently” and “... are independently selected from” are interchangeable and should be understood in a broad sense. They can mean that in different groups, the specific options expressed by the same symbols do not affect each other, or in the same group, the specific options expressed by the same symbols do not affect each other.
- each q is independently 0, 1, 2 or 3, and each R" is independently selected from hydrogen, deuterium, fluorine, and chlorine, which means:
- Formula Q-1 indicates that there are q substituents R" on the benzene ring, and each R" can be the same or different, and the options of each R" do not affect each other;
- Formula Q-2 indicates that there are q substituents R" on each benzene ring of biphenyl, and the number q of R" substituents on the two benzene rings can be the same or different, and each R" can be the same or different, and the options of each R" do not affect each other.
- substituted or unsubstituted means that the functional group recorded after the term may or may not have a substituent (hereinafter, for the convenience of description, the substituent is collectively referred to as Rc).
- substituent hereinafter, for the convenience of description, the substituent is collectively referred to as Rc).
- substituted or unsubstituted aryl refers to an aryl having a substituent Rc or an unsubstituted aryl.
- Rc can be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, etc.
- the number of carbon atoms of a substituted or unsubstituted functional group refers to the total number of carbon atoms.
- L is a substituted arylene group having 12 carbon atoms
- the total number of carbon atoms of the arylene group and the substituents thereon is 12.
- aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring.
- Aryl can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl.
- aryl can be a monocyclic aryl, a condensed ring aryl, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl and a condensed ring aryl connected by carbon-carbon bond conjugation, and two or more condensed ring aryl groups connected by carbon-carbon bond conjugation.
- condensed ring aryl can, for example, include bicyclic condensed aryl (e.g., naphthyl), tricyclic condensed aryl (e.g., phenanthrenyl, fluorenyl, anthracenyl), etc.
- Aryl does not contain heteroatoms such as B, N, O, S, P, Se, and Si.
- biphenyl, terphenyl, etc. are aryl.
- aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracenyl, phenanthrenyl, biphenyl, terphenyl, benzo[9,10]phenanthrenyl, pyrenyl, benzofluoranthenyl,
- the arylene group refers to a divalent group formed by further losing a hydrogen atom from an aryl group.
- the substituted aryl group may be one or more hydrogen atoms in the aryl group replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, halogenated alkyl groups, etc.
- the number of carbon atoms in the substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group with 18 carbon atoms means that the total number of carbon atoms in the aryl group and the substituents is 18.
- heteroaryl refers to a monovalent aromatic ring or a derivative thereof containing at least one heteroatom in the ring, and the heteroatom may be one or more of B, O, N, P, Si, Se and S.
- the heteroaryl may be a monocyclic heteroaryl or a polycyclic heteroaryl, in other words, the heteroaryl may be a single aromatic ring system or a plurality of aromatic ring systems conjugated by carbon-carbon bonds, and any aromatic ring system may be an aromatic monocyclic ring or an aromatic condensed ring.
- the heteroaryl group may include a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolinyl group, a quinoxalinyl group, a phenoxazinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, an
- heteroaryl groups of single aromatic ring system type
- N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of polycyclic system type connected by carbon-carbon bond conjugation.
- the heteroaryl group involved refers to a divalent group formed by further losing a hydrogen atom of the heteroaryl group.
- the substituted heteroaryl group may be a heteroaryl group in which one or more hydrogen atoms are replaced by groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc.
- groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, etc.
- the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituents on the heteroaryl group.
- the aryl group as a substituent in Ar 1 , Ar 2 , L, L 1 and L 2 may have 6 to 20 carbon atoms, for example, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms.
- Specific examples of the aryl group as a substituent include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, base.
- the number of carbon atoms of the heteroaryl group as a substituent in Ar 1 , Ar 2 , L, L 1 and L 2 may be 3 to 20, for example, the number of carbon atoms may be 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20.
- Specific examples of the heteroaryl group as a substituent include, but are not limited to, triazine, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolyl, quinazolinyl, quinoxalinyl and isoquinolyl.
- the non-positioned connecting bond refers to the single bond extending from the ring system. It means that one end of the connecting bond can be connected to any position in the ring system that the bond passes through, and the other end is connected to the rest of the compound molecule.
- the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms.
- the number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, and the like.
- the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
- trialkylsilyl include, but are not limited to, trimethylsilyl and triethylsilyl.
- haloalkyl group examples include, but are not limited to, trifluoromethyl.
- the carbon number of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3, 4, 5, 6, 7, 8, 9 or 10.
- Specific examples of the cycloalkyl group include, but are not limited to, cyclopentane, cyclohexane, and adamantane.
- the naphthyl group represented by formula (f) is connected to other positions of the molecule through two non-positional connecting bonds that penetrate the bicyclic ring, and its meaning includes any possible connection method shown in formulas (f-1) to (f-10).
- the dibenzofuranyl represented by formula (X') is connected to other positions of the molecule through a non-positional connecting bond extending from the middle of one side of the benzene ring, and its meaning includes any possible connection method shown in formula (X'-1) to formula (X'-4).
- one, two, three or four of A, B, C and D are groups represented by Formula 2.
- one or two of A, B, C and D are groups represented by Formula 2.
- the compound of formula 1 is selected from the structures shown in the following formulas I-1 to I-3:
- the organic compound has a structure as shown in the following formula II-1 to formula II-11:
- the compound has a structure as shown in the following formula II-1 to formula II-2:
- R 1 , R 2 , R 3 , R 4 , n 1 , n 2 , n 3 and n 4 have the same definitions as in formula 1, and Ar 1 , Ar 2 , L, L 1 , L 2 and a have the same definitions as in formula 2.
- Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 25 carbon atoms.
- Ar1 and Ar2 are each independently selected from a substituted or unsubstituted aryl group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17, 18, 19, 20 or 25 carbon atoms.
- the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms, a trimethylsilyl group, a trifluoromethyl group, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 12 carbon atoms; optionally, any two adjacent substituents in Ar 1 form a benzene ring or a fluorene ring; optionally, any two adjacent substituents in Ar 2 form a benzene ring or a fluorene ring.
- Ar 1 and Ar 2 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted carbazolyl.
- the substituents in Ar 1 and Ar 2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl; optionally, any two adjacent substituents in Ar 1 form a benzene ring; optionally, any two adjacent substituents in Ar 2 form a benzene ring.
- Ar 1 and Ar 2 are each independently selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups:
- the substituted group W has one or more substituents, and the substituents are independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, phenyl, naphthyl, biphenyl, dibenzofuranyl or dibenzothiophenyl, and when the number of the substituents is greater than 1, the substituents are the same or different.
- Ar 1 and Ar 2 are each independently selected from the group consisting of the following groups:
- Ar 1 and Ar 2 are each independently selected from the group consisting of:
- L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.
- L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19 or 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
- the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, an alkyl group having 1 to 5 carbon atoms or an aryl group having 6 to 12 carbon atoms.
- L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted fluorenylene, a substituted or unsubstituted phenanthrenylene, a substituted or unsubstituted dibenzofuranylene or a substituted or unsubstituted dibenzothiophenylene.
- the substituents in L, L1 and L2 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl or naphthyl.
- L, L1 and L2 are each independently selected from a single bond, a substituted or unsubstituted group Q; wherein the unsubstituted group Q is selected from the group consisting of the following groups:
- the substituted group Q has one or more substituents, each substituent is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, cyclopentane, cyclohexane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of the substituents is greater than 1, the substituents are the same or different.
- L1 and L2 are each independently selected from a single bond or the group consisting of the following groups:
- L1 and L2 are each independently selected from a single bond or the following groups:
- R 1 , R 2 , R 3 and R 4 are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl or trimethylsilyl.
- the organic compound is selected from the group consisting of the following compounds:
- the present application provides an electronic component, comprising an anode and a cathode arranged opposite to each other, and a functional layer arranged between the anode and the cathode; the functional layer comprises the organic compound of the present application.
- the functional layer includes a second hole transport layer, and the second hole transport layer includes the organic compound described in the present application.
- the electronic component is an organic electroluminescent device or a photoelectric conversion device.
- the electronic component is an organic electroluminescent device.
- the organic electroluminescent device may include an anode 100 , a hole transport layer 320 , an organic light emitting layer 330 , an electron transport layer 340 , and a cathode 200 , which are stacked in sequence.
- the organic electroluminescent device is a red organic electroluminescent device.
- the anode 100 includes the following anode material, which is optionally a material having a large work function that facilitates hole injection into the functional layer.
- anode materials include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combined metals and oxides such as ZnO:Al or SnO 2 : Sb; or conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline, but are not limited thereto.
- a transparent electrode including indium tin oxide (ITO) as an anode is included.
- the hole transport layer 320 includes the organic compound of the present application.
- the hole transport layer 320 includes a first hole transport layer 321 and a second hole transport layer 322 which are stacked, and relative to the second hole transport layer 322 , the first hole transport layer 321 is closer to the anode.
- the first hole transport layer 321 includes one or more hole transport materials, and the hole transport material can be selected from carbazole polymers, carbazole-linked triarylamine compounds or other types of compounds, and those skilled in the art can select them with reference to the prior art.
- the material of the first hole transport layer 321 is selected from the group consisting of the following compounds:
- the first hole transport layer 321 is compound NPB.
- the second hole transport layer 322 comprises the organic compound described in the present application.
- the organic light-emitting layer 330 may be composed of a single light-emitting layer material, or may include a main material and a doping material.
- the organic light-emitting layer 330 is composed of a main material and a doping material, and holes injected into the organic light-emitting layer 330 and electrons injected into the organic light-emitting layer 330 may be recombined in the organic light-emitting layer 330 to form excitons, and the excitons transfer energy to the main material, and the main material transfers energy to the doping material, thereby enabling the doping material to emit light.
- the main material of the organic light-emitting layer 330 may be a metal chelate compound, a bisphenylethylene derivative, an aromatic amine derivative, a dibenzofuran derivative or other types of materials, and the present application does not impose any special restrictions thereon.
- the main material may be a single main material or a mixed main material.
- the main material of the organic light-emitting layer 330 is RH-1
- the doping material of the organic light emitting layer 330 can be selected with reference to the prior art, for example, it can be selected from iridium (III) organic metal complex, platinum (II) organic metal complex, ruthenium (II) complex, beryllium complex, etc. Specific examples of the doped materials include, but are not limited to,
- the doping material of the organic light-emitting layer 340 is RD-1.
- the electron transport layer 340 may be a single-layer structure or a multi-layer structure, and may include one or more electron transport materials.
- the electron transport material may generally include a metal complex or/and a nitrogen-containing heterocyclic derivative, wherein the metal complex material may be selected from, for example, LiQ, Alq 3 , Bepq 2 , etc.; the nitrogen-containing heterocyclic derivative may be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a nitrogen-containing heterocyclic derivative, or a metal complex material.
- a condensed aromatic ring compound with a six-membered ring or a five-membered ring skeleton, etc. specific examples include but are not limited to 1,10-phenanthroline compounds such as ET-1, Bphen, NBphen, DBimiBphen, BimiBphen, or anthracene compounds, triazines or pyrimidine compounds containing hetero-nitrogen aromatic groups as shown below.
- the electron transport layer 340 is composed of ET-10 and LiQ.
- the cathode 200 may include a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer.
- cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; or multilayer materials such as LiF/Al, Liq/Al, LiO 2 /Al, LiF/Ca, LiF/Al and BaF 2 /Ca. It is preferred to include a metal electrode containing magnesium and silver as the cathode.
- a hole injection layer 310 may be provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321.
- the hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives or other materials, and the present application does not impose any particular restrictions thereon.
- the compound contained in the hole injection layer 310 is selected from the group consisting of the following compounds:
- the hole injection layer 310 is HAT-CN.
- an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340.
- the electron injection layer 350 may include inorganic materials such as alkali metal sulfides, alkali metal halides, or may be In one embodiment of the present application, the electron injection layer 350 is Yb.
- the electronic component is a photoelectric conversion device.
- the photoelectric conversion device may include an anode 100 and a cathode 200 disposed opposite to each other, and a functional layer 300 disposed between the anode 100 and the cathode 200; the functional layer 300 includes an organic compound provided in the present application.
- the photoelectric conversion device may include an anode 100, a hole transport layer 320, an organic light emitting layer 330, an electron transport layer 340 and a cathode 200 stacked in sequence.
- the hole transport layer 320 comprises the organic compound described in the present application.
- the photoelectric conversion device is a solar cell, especially an organic thin film solar cell.
- the third aspect of the present application provides an electronic device, comprising the electronic component provided by the second aspect of the present application.
- the electronic device is a first electronic device 400
- the first electronic device 400 includes the above-mentioned organic electroluminescent device.
- the first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, such as, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting lamp, an optical module, etc.
- the electronic device is a second electronic device 500, and the second electronic device 500 includes the above-mentioned photoelectric conversion device.
- the second electronic device 500 can be, for example, a solar power generation device, a light detector, a fingerprint recognition device, an optical module, a CCD camera or other types of electronic devices.
- the compounds whose synthesis methods are not mentioned in this application are all raw materials obtained through commercial channels.
- IMA1-1 (125.0 g, 335.26 mmol), sodium methoxide (27.2 g, 502.90 mmol) and toluene (1200 mL) were added to the reaction flask, stirred and heated to reflux, and reacted for 12 h. The heating was stopped, the reaction solution was cooled to room temperature, washed with water until neutral, and then separated. The organic phase was dried over anhydrous sodium sulfate, filtered, and toluene was removed by vacuum distillation. The crude product was recrystallized from ethyl acetate/petroleum ether to obtain white crystals of IMA1-2 (84.8 g, yield 74.2%).
- the reaction solution is cooled to room temperature and extracted with dichloromethane.
- the organic phase is washed with water until neutral, then separated, dried, filtered and concentrated. Recrystallized and purified using a mixed solvent of ethyl acetate and n-heptane.
- the obtained product is dried to obtain a white solid IMA1-6 (25.4 g, yield 87.2%).
- IMAX listed in Table 1 was synthesized by referring to the preparation method of IMA1, except that raw material 1 was used instead of 2-chlorofluorene in step (1), and raw material 2 was used instead of 2-biphenylboronic acid in step (6).
- the main raw materials used, the synthesized products and the yield of the last step are shown in Table 1.
- IM B1-4 was synthesized by the same preparation method as IMA1-4, except that IM B1-3 (Cas.113163-16-9, commercially available) was used to replace IMA1-3, and other conditions remained unchanged to obtain IM B1-4 (28.9 g, yield 69.5%).
- IM B1-5 was synthesized by the same preparation method as IMA1-5, except that IM B1-4 was used to replace IMA1-4, and other conditions remained unchanged to obtain IM B1-5 (21.2 g, yield 81.6%).
- IM B1-6 was synthesized by the same preparation method as IMA1-6, except that IM B1-5 was used to replace IMA1-5, and 4-chloro-2'-biphenylboronic acid was used to replace 2-biphenylboronic acid. Other conditions remained unchanged to obtain IM B1-6 (22.1 g, yield 79.3%).
- IM B1 was synthesized by the same preparation method as IMA1, except that IM B1-6 was used to replace IMA1-6. Other conditions remained unchanged to obtain IM B1 (19.4 g, yield 92.5%).
- IM BX was synthesized by the same preparation method as IM B1, except that raw material 3 in Table 2 was used instead of 4-chloro-2'-biphenyl borate. Other conditions remained unchanged. The structures of the raw materials used, intermediates in each step, and products and the yield of the last step are shown in Table 2.
- IM-c-a 50.0 g, 99.43 mmol
- tetrabutylammonium fluoride 5.2 g, 19.89 mmol
- dichloromethane 400 mL
- IMA1 (10.8 g, 25.78 mmol), 4-aminobiphenyl (4.5 g, 26.55 mmol), tris(dibenzylideneacetone)dipalladium (0.5 g, 0.52 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.5 g, 1.04 mmol) and sodium tert-butoxide (3.7 g, 38.66 mmol) were added to toluene (50 mL), heated to 108° C.
- the compounds in Table 3 were prepared by the same preparation method as compound A04, except that the intermediates in Table 3 were used to replace intermediate IMA1, raw material 4 was used to replace 4-aminobiphenyl, and raw material 5 was used to replace 4-bromobiphenyl, and other conditions remained unchanged; the structures of the materials and products used, the final step yield and mass spectrometry characterization results are all listed in Table 3.
- the compounds in Table 4 were prepared by the same method as compound D02, except that the intermediates in Table 4 were used to replace intermediate IMA4, and the raw material 6 was used to replace N-phenyl-1-naphthylamine, and other conditions remained unchanged; the structures, yields and mass spectrometry characterization results of the materials and products used are listed in Table 4.
- IMA1 (8.0 g, 19.09 mmol), biboric acid pinacol ester (5.8 g, 22.91 mmol), tris(dibenzylideneacetone)dipalladium (0.35 g, 0.38 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.36 g, 0.76 mmol) and potassium acetate (3.7 g, 38.18 mmol), 1,4-dioxane (100 mL) were added to the reaction bottle, heated to 80 ° C and stirred for 6 h; then cooled to room temperature, the reaction solution The mixture was washed with water until neutral, separated and washed with water until neutral, the organic phases were combined, dried, filtered, and the solvent was removed under reduced pressure; the crude product was recrystallized and purified using ethyl acetate/petroleum ether (volume ratio of 1:3) to obtain a
- IMA1-B (5.0 g, 9.79 mmol), N-[1,1 ⁇ -biphenyl]-4-yl-N-(4-bromophenylhydrazine)-9,9-dimethyl-9H-fluorene-2-amine (5.06 g, 9.79 mmol), toluene (60 mL), ethanol (20 mL), water (10 mL) and potassium carbonate (3.0 g, 21.65 mmol) were added to the reaction bottle, and the temperature was raised to 50°C-60°C with stirring and heating, and tetrakis(triphenylphosphine)palladium (0.23 g, 0.20 mmol) and tetrabutylammonium bromide (TBAB) (0.63 g, 1.95 mmol) were quickly added, and then the temperature was continued to rise to 70-75°C and refluxed for 18 hours.
- TBAB tetrabutylammonium bromide
- the compounds in Table 5 were prepared by the same method as compound E03, except that intermediate IM-Xy in Table 5 was used to replace intermediate IMA1, and raw material 7 was used to replace N-[1,1 ⁇ -biphenyl]-4-yl-N-(4-bromophenylhydrazine)-9,9-dimethyl-9H-fluorene-2-amine, and other conditions remained unchanged; the structures of the materials and products used, the final step yield and mass spectrometry characterization results are all listed in Table 5.
- Example 1 Red organic electroluminescent device
- ITO thickness is A substrate (made by Corning) was cut into a size of 40 mm ⁇ 40 mm ⁇ 0.7 mm and prepared into an experimental substrate with cathode, anode and insulating layer patterns using a photolithography process. The surface was treated using ultraviolet ozone and O 2 :N 2 plasma to remove surface scum and improve the substrate anode work function.
- the HAT-CN is formed into a hole injection layer (HIL), and NPB is evaporated on the HAT-CN layer to form The first hole transport layer (HTL-1) is formed.
- HIL hole injection layer
- NPB is evaporated on the HAT-CN layer to form
- the first hole transport layer (HTL-1) is formed.
- Compound A04 is then evaporated on the first hole transport layer to form a layer with a thickness of The second hole transport layer (HTL-2) is formed.
- HTL-2 The second hole transport layer
- RH-1:RD-1 was co-evaporated on the second hole transport layer at a film thickness ratio of 97%:3% to form a film with a thickness of of an organic light-emitting layer (red light-emitting layer, R-EML).
- ET-10 and LiQ were co-evaporated at an evaporation rate ratio of 4:6 to form a film with a thickness of
- the electron transport layer (ETL) is formed by evaporating Yb on the electron transport layer to form a layer with a thickness of
- magnesium and silver were vacuum evaporated on the electron injection layer at an evaporation rate ratio of 1:10 to form a layer with a thickness of cathode.
- the cathode is evaporated
- the CP-1 is formed to form an organic cover layer (CPL), thereby completing the manufacture of a red organic electroluminescent device.
- Embodiments 2 to 40 are identical to Embodiments 2 to 40:
- Examples 2 to 40 organic electroluminescent devices were prepared by the same method as in Example 1, except that compounds A12 to E56 shown in Table 8 were used instead of compound A04 in Example 1 when forming the second hole transport layer.
- the devices prepared in each embodiment and comparative example were subjected to performance tests, wherein the IVL (operating voltage, current efficiency, color coordinates) data were tested at a current density of 10 mA/cm 2 , and the device T 95 life was tested at a constant current density of 20 mA/cm 2.
- the device performance is shown in Table 8.
- the organic electroluminescent devices prepared in Examples 1 to 40 using the organic compounds of the present application as the second hole transport layer have improved performances compared with the devices of Comparative Examples 1 to 4.
- the current efficiency (Cd/A) is increased by at least 13.5%
- the lifespan (T 95 ) is increased by at least 16.1%. It can be seen that using the organic compounds of the present application as the second hole transport layer of the organic electroluminescent device can significantly improve the luminous efficiency and T 95 lifespan of the organic electroluminescent device.
- the structure of the organic compound of the present application contains a multi-spiro ring structure formed by a cycloalkyl group and two or more fluorene planes, so that the fluorene plane structure forms a large spiro ring in space, which can effectively improve the mobility of holes and is suitable for the second hole transport layer of the organic electroluminescent device, so that the organic electroluminescent device prepared by it has the characteristics of low voltage and high efficiency.
- the conjugated planes in a spiro ring manner the stacking between molecules can be reduced in space, the amorphous state of the material during film formation can be improved, and it has better stability when used in organic electroluminescent devices.
- the life of the organic electroluminescent device of the embodiment of the present application is significantly improved. More specifically, the spiro ring part of compound A has a non-aromatic double bond, which is easy to polymerize under the action of an electric field, resulting in poor device characteristics; the aromatic amine of compound B is connected to the middle benzene ring, resulting in poor planar conjugation characteristics, which further leads to relatively poor device performance.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
涉及一种有机化合物及包含其的电子元件和电子装置。所述有机化合物结构式如式(I)所示,将该有机化合物应用于有机电致发光器件中,可显著改善器件的性能。
Description
相关申请的交叉引用
本申请要求于2022年10月24日递交的申请号为202211304334.9的中国专利申请的优先权,在此引用上述中国专利申请的内容全文以作为本申请的一部分。
本申请属于有机材料技术领域,尤其涉及一种有机化合物及包含其的电子元件和电子装置。
有机电致发光器件(OLEDs)为在两个金属电极之间通过旋涂或者真空蒸镀沉积一层有机材料制备而成的器件,经典的三层有机电致发光器件包含空穴传输层、有机发光层和电子传输层。由阳极产生的空穴经空穴传输层和由阴极产生的电子经电子传输层结合在有机发光层形成激子,而后发光。有机电致发光器件可以根据需要通过改变有机发光层的材料来调节发射各种需要的光。
目前,基于OLED发光与显示技术的商品已经实现产业化。与液晶类显示技术相比,OLED显示技术具有自发光、无辐射、质量轻、厚度薄、广视角、宽色域、颜色稳定、响应速度快、环境适应强、可实现柔性显示等诸多优点。因此,OLED显示技术获得越来越多的关注和相应的技术投入。
芳香胺化合物可用于空穴传输层中的空穴传输材料。例如,用杂芳环在芴基的9位处取代的一元胺衍生物已被报道作为有用的材料,用于提高有OLED器件的寿命。然而,仍存在与解决装置发光效率和寿命相关的问题。
因此,需要进一步开发用于具有长寿命的有机EL装置的材料以及使用该材料的有机EL装置。
发明内容
针对现有技术存在的上述问题,本申请的目的在于提供一种有机化合物及包含其的电子元件和电子装置,所述有机化合物可以改善电子元件和电子装置的性能。
本申请的第一方面提供一种有机化合物,其具有式1所示的结构:
其中,n和m相同或不同,且各自独立地选自1、2或3;
R1、R2、R3和R4相同或不同,且各自独立地选自氘、卤素基团、氰基、碳原子数为1~10的烷基或碳原子数为3~12的三烷基硅基;
n1表示R1的个数,且n1选自0、1、2、3或4,当n1大于1时,任意两个R1相同或不同;
n2表示R2的个数,且n2选自0、1、2、3或4,当n2大于1时,任意两个R2相同或不同;
n3表示R3的个数,且n3选自0、1、2、3或4,当n3大于1时,任意两个R3相同或不同;
n4表示R4的个数,且n4选自0、1、2、3或4,当n4大于1时,任意两个R4相同或不同;
A、B、C和D相同或不同,分别独立地选自氢或式2所示的基团,且A、B、C、D中至少有一个为式2所示的基团;
a表示L的个数,且a选自1或2;
Ar1和Ar2相同或不同,且各自独立地选自碳原子数为6~40的取代或未取代的芳基、碳原子数为3~40
的取代或未取代的杂芳基;
L、L1和L2相同或不同,且各自独立地选自单键、碳原子数为6~30的取代或未取代的亚芳基、碳原子数为3~30的取代或未取代的亚杂芳基;
Ar1、Ar2、L、L1和L2中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、碳原子数为1~10的烷基、碳原子数为3~12的三烷基硅基、碳原子数为1~10的卤代烷基、碳原子数为3~10的环烷基、碳原子数为6~20的芳基或碳原子数为3~20的杂芳基;任选地,Ar1中的任意两个相邻的取代基形成饱和或不饱和的3~15元环;任选地,Ar2中的任意两个相邻的取代基形成饱和或不饱和的3~15元环。
本申请的有机化合物为具有多螺环结构的三芳基胺类化合物,这种多螺环结构可提升分子的载流子迁移率,并且可以增加分子的扭曲度,能够有效避免芴平面之间的堆叠,抑制分子结晶,从而提升分子的成膜性;同时,这种结构也有利于增加分子的玻璃化转变温度,提升材料的蒸镀稳定性,并改善器件的寿命。
本申请的第二方面提供一种电子元件,包括相对设置的阳极和阴极,以及设于所述阳极和所述阴极之间的功能层;所述功能层包含上述的有机化合物。
本申请的第三方面提供一种电子装置,包括第二方面所述的电子元件。
本申请的其他特征和优点将在随后的具体实施方式部分予以详细说明。
附图是用来提供对本申请的进一步理解,并且构成说明书的一部分,与下面的具体实施方式一起用于解释本申请,但并不构成对本申请的限制。
图1是本申请一种实施方式的有机电致发光器件的结构示意图。
图2是本申请一种实施方式的第一电子装置的示意图。
图3是本申请一种实施方式的光电转化器件的结构示意图。
图4是本申请一种实施方式的第二电子装置的示意图。
附图标记
100、阳极;200、阴极;300、功能层;310、空穴注入层;320、空穴传输层;321、第一空穴传输
层;322、第二空穴传输层;330、有机发光层;340、电子传输层;350、电子注入层;360、光电转化层;400、第一电子装置;500、第二电子装置。
100、阳极;200、阴极;300、功能层;310、空穴注入层;320、空穴传输层;321、第一空穴传输
层;322、第二空穴传输层;330、有机发光层;340、电子传输层;350、电子注入层;360、光电转化层;400、第一电子装置;500、第二电子装置。
现在将参考附图更全面地描述示例性实施方式。然而,示例性实施方式能够以多种形式实施,且不应被理解为限于在此阐述的范例;相反,提供这些实施例使得本申请将更加全面和完整,并将示例性实施方式的构思全面地传达给本领域的技术人员。所描述的特征、结构或特性可以以任何合适的方式结合在一个或更多个实施方式中。在下面的描述中,提供许多具体细节从而给出对本申请的实施例的充分理解。
第一方面,本申请提供一种有机化合物,其具有式1所示的结构:
其中,n和m相同或不同,且各自独立地选自1、2或3;
R1、R2、R3和R4相同或不同,且各自独立地选自氘、卤素基团、氰基、碳原子数为1~10的烷基或碳原子数为3~12的三烷基硅基;
n1表示R1的个数,且n1选自0、1、2、3或4,当n1大于1时,任意两个R1相同或不同;
n2表示R2的个数,且n2选自0、1、2、3或4,当n2大于1时,任意两个R2相同或不同;
n3表示R3的个数,且n3选自0、1、2、3或4,当n3大于1时,任意两个R3相同或不同;
n4表示R4的个数,且n4选自0、1、2、3或4,当n4大于1时,任意两个R4相同或不同;A、B、C和D相同或不同,分别独立地选自氢或式2所示的基团,且A、B、C、D中至少有一个为式2所示的基团;
Ar1和Ar2相同或不同,且各自独立地选自碳原子数为6~40的取代或未取代的芳基、碳原子数为3~40的取代或未取代的杂芳基;
L、L1和L2相同或不同,且各自独立地选自单键、碳原子数为6~30的取代或未取代的亚芳基、碳原子数为3~30的取代或未取代的亚杂芳基;
a表示L的个数,且a选自1或2;当a=2时,是指两个L依次连接;
Ar1、Ar2、L、L1和L2中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、碳原子数为1~10的烷基、碳原子数为3~12的三烷基硅基、碳原子数为1~10的卤代烷基、碳原子数为3~10的环烷基、碳原子数为6~20的芳基或碳原子数为3~20的杂芳基;任选地,Ar1中的任意两个相邻的取代基形成饱和或不饱和的3~15元环;任选地,Ar2中的任意两个相邻的取代基形成饱和或不饱和的3~15元环。
本申请中,术语“任选”、“任选地”意着随后所描述的事件或者环境可以但不必发生,该说明包括该事情或者环境发生或者不发生的场合。例如,“任选地,任意两个相邻取代基××形成环”意味着这两个取代基可以形成环但不是必须形成环,包括:两个相邻的取代基形成环的情景和两个相邻的取代基不形成环的情景。再比如,“任选地,Ar2中的任意两个相邻的取代基形成饱和或不饱和的3~15元环”是指Ar2中的任意两个相邻的取代基可以相互连接形成饱和或不饱和的3~15元环,或者Ar2中的任意两个相邻的取代基也可以各自独立的存在。
“任意两个相邻的取代基”可以包括同一个原子上具有两个取代基,还可以包括两个相邻的原子上分别具有一个取代基;其中,当同一个原子上具有两个取代基时,两个取代基可以与其共同连接的该原子形成饱和或不饱和的环;当两个相邻的原子上分别具有一个取代基时,这两个取代基可以稠合成环。
本申请中,芴基可以被1个或2个或更多个取代基取代,在上述芴基被取代的情况下,可以为:
等,但并不限定于此。
本申请中,所采用的描述方式“各……独立地为”与“……分别独立地为”和“……独立地选自”可以互换,均应做广义理解,其既可以是指在不同基团中,相同符号之间所表达的具体选项之间互相不影响,也可以表示在相同的基团中,相同符号之间所表达的具体选项之间互相不影响。例如,“其中,各q独立地为0、1、2或3,各R”独立地选自氢、氘、氟、氯”,其含义是:式Q-1表示苯环上有q个取代基R”,各个R”可以相同也可以不同,每个R”的选项之间互不影响;式Q-2表示联苯的每一个苯环上有q个取代基R”,两个苯环上的R”取代基的个数q可以相同或不同,各个R”可以相同也可以不同,每个R”的选项之间互不影响。
本申请中,“取代或未取代的”这样的术语是指,在该术语后面记载的官能团可以具有或不具有取代基(下文为了便于描述,将取代基统称为Rc)。举例来讲,“取代或未取代的芳基”是指具有取代基Rc的芳基或者没有取代的芳基。其中上述的取代基即Rc例如可以为氘、卤素基团、氰基、杂芳基、芳基、三烷基硅基、烷基、卤代烷基、环烷基等。
本申请中,取代或未取代的官能团的碳原子数,指的是所有碳原子数。举例而言,若L为碳原子数为12的取代的亚芳基,则亚芳基及其上的取代基的所有碳原子数为12。
本申请中,芳基指的是衍生自芳香碳环的任选官能团或取代基。芳基可以是单环芳基(例如苯基)或多环芳基,换言之,芳基可以是单环芳基、稠环芳基、通过碳碳键共轭连接的两个或者更多个单环芳基、通过碳碳键共轭连接的单环芳基和稠环芳基、通过碳碳键共轭连接的两个或者更多个稠环芳基。即,除非另有说明,通过碳碳键共轭连接的两个或者更多个芳香基团也可以视为本申请的芳基。其中,稠环芳基例如可以包括双环稠合芳基(例如萘基)、三环稠合芳基(例如菲基、芴基、蒽基)等。芳基中不含有B、N、O、S、P、Se和Si等杂原子。举例而言,在本申请中,联苯基、三联苯基等为芳基。芳基的实例可以包括但不限于,苯基、萘基、芴基、蒽基、菲基、联苯基、三联苯基、苯并[9,10]菲基、芘基、苯并荧蒽基、基等。本申请中,涉及的亚芳基是指芳基进一步失去一个氢原子所形成的二价基团。
本申请中,取代的芳基可以是芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、卤代烷基等基团取代。应当理解地是,取代的芳基的碳原子数,指的是芳基和芳基上的取代基的碳原子总数,例如碳原子数为18的取代的芳基,指的是芳基和取代基的总碳原子数为18。
本申请中,杂芳基是指环中包含至少一个杂原子的一价芳香环或其衍生物,杂原子可以是B、O、N、P、Si、Se和S中的一种或多种。杂芳基可以是单环杂芳基或多环杂芳基,换言之,杂芳基可以是单个芳香环体系,也可以是通过碳碳键共轭连接的多个芳香环体系,且任一芳香环体系为一个芳香单环或者一个芳香稠环。示例地,杂芳基可以包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、噁唑基、噁二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、吩噁嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并噁唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、噻吩并噻吩基、苯并呋喃基、菲咯啉基、异噁唑基、噻二唑基、吩噻嗪基、硅芴基、二苯并呋喃基以及N-苯基咔唑基、N-吡啶基咔唑基、N-甲基咔唑基等,而不限于此。其中,噻吩基、呋喃基、菲咯啉基等为单个芳香环体系类型的杂芳基,N-苯基咔唑基、N-吡啶基咔唑基为通过碳碳键共轭连接的多环体系类型的杂芳基。本申请中,涉及的亚杂芳基是指杂芳基进一步失去一个氢原子所形成的二价基团。
本申请中,取代的杂芳基可以是杂芳基中的一个或者两个以上氢原子被诸如氘原子、卤素基团、氰基、芳基、杂芳基、三烷基硅基、烷基、环烷基、卤代烷基等基团取代。应当理解地是,取代的杂芳基的碳原子数,指的是杂芳基和杂芳基上的取代基的碳原子总数。
本申请中,作为Ar1、Ar2、L、L1和L2中的取代基的芳基的碳原子数可以为6~20,例如碳原子数可以为6、7、8、9、10、11、12、13、14、15、16、17、18、19或20,作为取代基的芳基的具体实例包括但不限于,苯基、联苯基、萘基、芴基、菲基、蒽基、基。
本申请中,作为Ar1、Ar2、L、L1和L2中的取代基的杂芳基的碳原子数可以为3~20,例如碳原子数可以为3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19或20,作为取代基的杂芳基的具体实例包括但不限于,三嗪基、吡啶基、嘧啶基、咔唑基、二苯并呋喃基、二苯并噻吩基、喹啉基、喹唑啉基、喹喔啉基、异喹啉基。
本申请中,不定位连接键涉及的是从环体系中伸出的单键其表示该连接键的一端可以连接该键所贯穿的环体系中的任意位置,另一端连接化合物分子其余部分。
本申请中,碳原子数为1~10的烷基可以包括碳原子数1至10的直链烷基和碳原子数3至10的支链烷基。烷基的碳原子数例如可以为1、2、3、4、5、6、7、8、9、10,烷基的具体实例包括但不限于,甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基、正辛基、2-乙基己基、壬基、癸基、3,7-二甲基辛基等。
本申请中,卤素基团例如可以为氟、氯、溴、碘。
本申请中,三烷基硅基的具体实例包括但不限于,三甲基硅基、三乙基硅基。
本申请中,卤代烷基的具体实例包括但不限于,三氟甲基。
本申请中,碳原子数为3~10的环烷基的碳原子数例如可以为3、4、5、6、7、8、9或10。环烷基的具体实例包括但不限于,环戊烷、环己烷、金刚烷。
举例而言,如下式(f)中所示地,式(f)所表示的萘基通过两个贯穿双环的不定位连接键与分子其他位置连接,其所表示的含义,包括如式(f-1)~式(f-10)所示出的任一可能的连接方式。
再举例而言,如下式(X')中所示地,式(X')所表示的二苯并呋喃基通过一个从一侧苯环中间伸出的不定位连接键与分子其他位置连接,其所表示的含义,包括如式(X'-1)~式(X'-4)所示出的任一可能的连接方式。
在本申请一些实施方式中,A、B、C和D中的1个、2个、3个或4个为式2所示的基团。
可选地,A、B、C和D中的1个或2个为式2所示的基团。
在本申请一些实施方式中,式1化合物选自以下式I-1~I-3所示的结构:
上述式I-1至I-3中,A、B、C、D、R1、R2、R3、R4、n1、n2、n3和n4的定义同式1。
可选地,所述有机化合物具有如下式II-1~式II-11所示的结构:
可选地,所述化合物具有如下式II-1~式II-2所示的结构:
上述式II-1~式II-11中,R1、R2、R3、R4、n1、n2、n3和n4的定义同式1,Ar1、Ar2、L、L1、L2和a的定义同式2。
可选地,式1中的选自单键。
在本申请的一些实施方式中,Ar1和Ar2各自独立地选自碳原子数为6~25的取代或未取代的芳基、碳原子数为12~25的取代或未取代的杂芳基。例如,Ar1和Ar2各自独立地选自碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24或25的取代或未取代的芳基,碳原子数为12、13、14、15、16、17、18、19、20或25的取代或未取代的杂芳基。
可选地,Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1~5的烷基、三甲基硅基、三氟甲基、碳原子数为5~10的环烷基或碳原子数为6~12的芳基;任选地,Ar1中的任意两个相邻的取代基形成苯环或芴环;任选地,Ar2中的任意两个相邻的取代基形成苯环或芴环。
在本申请的一些实施方式中,Ar1和Ar2各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的三联苯基、取代或未取代的螺二芴基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基或取代或未取代的咔唑基。
可选地,Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、三氟甲基、环戊烷、环己烷、苯基、萘基、联苯基、二苯并呋喃基、二苯并噻吩基或咔唑基;任选地,Ar1中的任意两个相邻的取代基形成苯环;任选地,Ar2中的任意两个相邻的取代基形成苯环。
在本申请的一些实施方式中,Ar1和Ar2各自独立地选自取代或未取代的基团W,其中未取代的基团W选自以下基团:
其中,取代的基团W中具有一个或两个以上取代基,所述取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、三氟甲基、环戊烷、环己烷、苯基、萘基、联苯基、二苯并呋喃基或二苯并噻吩基,且当所述取代基个数大于1时,各取代基相同或不同。
在本申请的一些实施方式中,Ar1和Ar2各自独立地选自以下基团构成的组:
可选地,Ar1和Ar2各自独立地选自以下基团构成的组:
在本申请的一些实施方式中,L、L1和L2各自独立地选自单键或碳原子数为6~20的取代或未取代的亚芳基、碳原子数为12~18的取代或未取代的亚杂芳基。例如,L、L1和L2各自独立地选自单键,碳原子数为6、7、8、9、10、11、12、13、14、15、16、17、18、19或20的取代或未取代的亚芳基,碳原子数为12、13、14、15、16、17或18的取代或未取代的亚杂芳基。
可选地,L、L1和L2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1~5的烷基或碳原子数为6~12的芳基。
在本申请的一些实施方式中,L、L1和L2各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚芴基、取代或未取代的亚菲基、取代或未取代的亚二苯并呋喃基或取代或未取代的亚二苯并噻吩基。
可选地,L、L1和L2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基或萘基。
在本申请的一些实施方式中,L、L1和L2各自独立地选自单键、取代或未取代的基团Q;其中,未取代的基团Q选自以下基团构成的组:
其中,取代的基团Q中具有一个或两个以上取代基,各取代基独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、环戊烷、环己烷、苯基、萘基、联苯基、二苯并呋喃基、二苯并噻吩基或咔唑基,且当所述取代基个数大于1时,各取代基相同或不同。
在本申请的一些实施方式中,式1中的选自单键或者以下基团构成的组:
可选地,式1中的选自单键或者以下基团构成的组:
在本申请的一些实施方式中,L1和L2各自独立地选自单键或者以下基团构成的组:
进一步可选地,L1和L2各自独立地选自单键或者以下基团构成的组:
在本申请的一些实施方式中,各自独立地选自以下基团构成的组:
在本申请的一些实施方式中,R1、R2、R3和R4各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基或三甲基硅基。
在本申请的一些更具体的实施方式中,所述有机化合物选自如下化合物所构成的组:
第二方面,本申请提供一种电子元件,包括相对设置的阳极和阴极,以及设于阳极和阴极之间的功能层;所述功能层包含本申请的有机化合物。
可选地,功能层包括第二空穴传输层,第二空穴传输层包含本申请所述的有机化合物。
可选地,所述电子元件有机电致发光器件或光电转换器件。
在一种实施方式中,电子元件为有机电致发光器件。如图1所示,有机电致发光器件可以包括依次层叠设置的阳极100、空穴传输层320、有机发光层330、电子传输层340和阴极200。
在一种具体的实施方式中,有机电致发光器件为红色有机电致发光器件。
可选地,阳极100包括以下阳极材料,其可选地是有助于空穴注入至功能层中的具有大逸出功(功函数,work function)材料。阳极材料具体实例包括:金属如镍、铂、钒、铬、铜、锌和金或它们的合金;金属氧化物如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);组合的金属和氧化物如ZnO∶Al或SnO2∶Sb;或导电聚合物如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDT)、聚吡咯和聚苯胺,但不限于此。优选包括包含氧化铟锡(铟锡氧化物,indiumtin oxide)(ITO)作为阳极的透明电极。
可选地,所述空穴传输层320包含本申请的有机化合物。
可选地,所述空穴传输层320包括层叠设置的第一空穴传输层321和第二空穴传输层322,且相对所述第二空穴传输层322,所述第一空穴传输层321更靠近所述阳极。
可选地,第一空穴传输层321包括一种或者多种空穴传输材料,空穴传输材料可以选自咔唑多聚体、咔唑连接三芳胺类化合物或者其他类型的化合物,本领域技术人员可参照现有技术选择。例如,所述第一空穴传输层321的材料选自以下化合物所构成的组:
在一种具体实施方式中,第一空穴传输层321为化合物NPB。
可选地,所述第二空穴传输层322包含本申请所述的有机化合物。
可选地,有机发光层330可以由单一发光层材料组成,也可以包括主体材料和掺杂材料。可选地,有机发光层330由主体材料和掺杂材料组成,注入有机发光层330的空穴和注入有机发光层330的电子可以在有机发光层330复合而形成激子,激子将能量传递给主体材料,主体材料将能量传递给掺杂材料,进而使得掺杂材料能够发光。
有机发光层330的主体材料可以为金属螯合类化合物、双苯乙烯基衍生物、芳香族胺衍生物、二苯并呋喃衍生物或者其他类型的材料,本申请对此不做特殊的限制。主体材料可以为单一主体材料,也可以为混合主体材料。
在本申请的一种实施方式中,有机发光层330的主体材料为RH-1
有机发光层330的的掺杂材料可参照现有技术选择,例如可以选自铱(III)有机金属络合物、铂(II)有机金属络合物、钌(II)络合物、铍络合物等。所掺杂材料的具体实例包括但不限于,
在本申请的一种实施方式中,有机发光层340的掺杂材料为RD-1。
可选地,电子传输层340可以为单层结构,也可以为多层结构,其可以包括一种或者多种电子传输材料,电子传输材料通常可以包含金属络合物或/或含氮杂环衍生物,其中,所述金属络合物材料例如可以选自LiQ、Alq3、Bepq2等;所述含氮杂环衍生物可以为具有含氮六元环或五元环骨架的芳香族环、具有含氮
六元环或五元环骨架的稠合芳香族环化合物等,具体实例包括但不限于,ET-1、Bphen、NBphen、DBimiBphen、BimiBphen等1,10-菲咯啉类化合物,或者结构如下所示的含杂氮芳基的蒽类化合物、三嗪类或嘧啶类化合物。在本申请的一种实施方式中,电子传输层340由ET-10和LiQ组成。
本申请中,阴极200可以包括阴极材料,其是有助于电子注入材料至功能层中的具有小逸出功的材料。阴极材料的具体实例包括但不限于,金属如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅或它们的合金;或多层材料如LiF/Al、Liq/Al、LiO2/Al、LiF/Ca、LiF/Al和BaF2/Ca。优选包括包含镁和银的金属电极作为阴极。
可选地,如图1所示,在阳极100和第一空穴传输层321之间还可以设置有空穴注入层310,以增强向第一空穴传输层321注入空穴的能力。空穴注入层310可以选用联苯胺衍生物、星爆状芳基胺类化合物、酞菁衍生物或者其他材料,本申请对此不做特殊的限制。例如,空穴注入层310含有的化合物选自以下化合物所构成的组:
在本申请的一种具体实施方式中,空穴注入层310为HAT-CN。
可选地,如图1所示,在阴极200和电子传输层340之间还设置有电子注入层350,以增强向电子传输层340注入电子的能力。电子注入层350可以包括有碱金属硫化物、碱金属卤化物等无机材料,或者可
以包括碱金属与有机物的络合物。在本申请的一种具体实施方式中,电子注入层350为Yb。
按照另一种实施方式,电子元件为光电转化器件。如图3所示,该光电转化器件可以包括相对设置的阳极100和阴极200,以及设于阳极100和阴极200之间的功能层300;功能层300包含本申请所提供的有机化合物。
按照一种具体的实施方式,如图3所示,光电转化器件可包括依次层叠设置的阳极100、空穴传输层320、有机发光层330、电子传输层340和阴极200。可选地,所述空穴传输层320包含本申请所述的有机化合物。
可选地,光电转化器件为太阳能电池,尤其是有机薄膜太阳能电池。本申请第三方面提供一种电子装置,包括本申请第二方面提供的电子元件。
按照一种实施方式,如图2所示,所述电子装置为第一电子装置400,该第一电子装置400包括上述有机电致发光器件。第一电子装置400例如可以为显示装置、照明装置、光通讯装置或者其他类型的电子装置,例如可以包括但不限于电脑屏幕、手机屏幕、电视机、电子纸、应急照明灯、光模块等。
按照另一种实施方式,如图4所示,所述电子装置为第二电子装置500,第二电子装置500包括上述光电转化器件。第二电子装置500例如可以为太阳能发电设备、光检测器、指纹识别设备、光模块、CCD相机或则其他类型的电子装置。
下面结合合成例来具体说明本申请的有机化合物的合成方法,但是本申请并不因此而受到任何限制。
本申请中未提到的合成方法的化合物的都是通过商业途径获得的原料产品。
合成例
1、IMAX的合成
(1)在氮气保护下,向反应瓶中加入2-氯芴(80.0g,398.66mmol)、丙烯酸甲酯(75.5g,877.06mmol)、氢氧化钠(50%水溶液,797.33mmol)和甲苯(800mL),搅拌加热至回流,反应2h。停止加热,反应液降至室温后,用去离子水洗至中性,然后经过分液,有机相采用无水硫酸钠干燥,过滤,减压蒸馏除去甲苯,所得粗品用乙酸乙酯/石油醚重结晶后得到白色晶体IMA1-1(126.0g,收率84.8%)。
(2)在氮气保护下,向反应瓶中加入IMA1-1(125.0g,335.26mmol)、甲醇钠(27.2g,502.90mmol)和甲苯(1200mL),搅拌加热至回流,反应12h。停止加热,反应液降至室温后,水洗至中性,然后分液,有机相采用无水硫酸钠干燥,过滤,减压蒸馏除去甲苯,所得粗品用乙酸乙酯/石油醚重结晶后得到白色晶体IMA1-2(84.8g,收率74.2%)。
(3)向反应瓶中加入IM A1-2(84.0g,246.48mmol)和冰乙酸(800mL),搅拌均匀后,缓慢滴入浓度为12M的浓盐酸(25mL,300.00mmol),滴加完毕后缓慢升温至回流,持续搅拌8h。反应液倒入900mL水中,析出白色固体,过滤并用去离子水洗至中性,所得粗品用乙酸乙酯/石油醚(体积比为1:4)的洗
脱剂过硅胶色谱柱提纯后,减压蒸出溶剂得到白色固体IMA1-3(34.8g,收率49.9%)。
(4)将IMA1-3(34.0g,120.24mmol)、邻苯二酚(17.2g,156.31mmol)和甲苯(500mL)加入带有回流分水器的反应瓶中,升温搅拌至原料溶清,然后缓慢滴入浓硫酸(98%,1.2g,12.02mmol)。然后继续搅拌回流分水至TLC显示IMA1-3无剩余时停止反应。反应液降至室温后,水洗至中性,萃取、分液后所得有机相用无水硫酸钠干燥,再经过过滤、减压蒸馏除去溶剂,粗品用二乙醚进行重结晶,得到IMA1-4(32.6g,收率72.4%)。
(5)将IMA1-4(32.0g,85.36mmol)和二氯甲烷(300mL)搅拌溶清后降温至0℃,缓慢滴加三溴化硼(32.1g,128.05mmol),保温反应8h。然后缓慢升温至室温,再加入NaOH(6.9g,170.73mmol)、四丁基硫酸氢铵(n-Bu4NHSO4)(5.8g,17.07mmol)、去离子水(10mL),再补加二氯甲烷(100mL),搅拌反应3天。加入400mL去离子水终止反应,分液后有机相经过水洗、分液、干燥、过滤、减压蒸馏除去溶剂,得到固体有机物。再用二氯甲烷/石油醚重结晶提纯后,得到IMA1-5(24.6g,收率83.3%)。
(6)在氮气保护下,向反应瓶中加入IMA1-5(24.0g,69.43mmol)、2-联苯硼酸(14.4g,72.89mmol)、甲苯(200mL)、乙醇(80mL)、水(40mL)和碳酸钾(21.1g,152.75mmol);开启搅拌,加热升温至50℃-60℃,迅速加入四(三苯基膦)钯(1.6g,1.39mmol)和四丁基溴化铵(4.5g,13.88mmol),然后继续升温至70℃-75℃回流,反应18h。反应液降至室温,用二氯甲烷萃取,有机相水洗至中性,然后分液、干燥、过滤、浓缩。采用乙酸乙酯和正庚烷混合溶剂重结晶提纯。所得产物烘干后得白色固体IMA1-6(25.4g,收率87.2%)。
(7)在氮气保护下,向反应瓶中加入IMA1-6(25.0g,59.67mmol)和二氯甲烷(200mL);开启搅拌,并将体系降温至0℃,缓慢滴加甲基磺酸(1.2g,12.53mmol),保温搅拌1.5h;然后降温至-10℃加入100mL冰水停止反应。再自然升温降至室温,用二氯甲烷萃取,有机相水洗至中性,然后分液、干燥、过滤、浓缩。用乙酸乙酯和正庚烷混合溶剂重结晶至LC>98%,烘干得白色固体IMA1(24.2g,收率96.8%)。
参照IMA1的制备方法合成表1所列的IMAX,不同之处在于,使用原料1代替第(1)步中的2-氯芴,使用原料2代替第(6)步中的2-联苯硼酸。其中,使用的主要原料、合成的产物及最后一步收率如表1所示。
表1
2、IM BX的合成
(1)IM B1的合成
采用与IMA1-4相同的制备方法合成IM B1-4,不同之处在于:采用IM B1-3(Cas.113163-16-9市售)替换IMA1-3,其他条件不变,得到IM B1-4(28.9g,收率69.5%)。
采用与IMA1-5相同的制备方法合成IM B1-5,不同之处在于:采用IM B1-4替换IMA1-4,其他条件不变,得到IM B1-5(21.2g,收率81.6%)。
采用与IMA1-6相同的制备方法合成IM B1-6,不同之处在于:分别采用IM B1-5替换IMA1-5,用4-氯-2'-硼酸联苯代替2-联苯硼酸,其他条件不变,得到IM B1-6(22.1g,收率79.3%)。
采用与IMA1相同的制备方法合成IM B1,不同之处在于:采用IM B1-6替换IMA1-6,其他条件不变,得到IM B1(19.4g,收率92.5%)。
采用与IM B1相同的制备方法合成IM BX,不同之处在于:用表2中的原料3代替4-氯-2'-硼酸联苯,其他条件不变,所用原料及各步中间体以及产物的结构和最后一步收率见表2。
表2
3、IM CX的合成
IM C1和IM C2的合成
(1)在氮气保护下,向三口烧瓶中加入9-(三甲基甲硅烷基)芴(40.0g,167.98mmol)与干燥的THF(350mL),用液氮/丙酮浴将体系降温至-78℃,然后缓慢滴加浓度为2M的正丁基锂的正己烷溶液(90mL,180.00mmol),滴加完毕后保温搅拌2h;然后缓慢滴加溶有1,2-双甲苯氧基乙烷(34.0g,91.88mmol)的THF溶液200mL,滴完后保温搅拌1h;然后自然升温至室温,加入200mL去离子水淬灭反应。用稀盐酸调节反应液pH值至6.0,再用二氯甲烷萃取反应液,再经过分液、干燥、过滤,所得有机相经减压蒸馏除去溶剂,所得粗品用二氯甲烷/石油醚重结晶纯化得到IM-c-a(50.9g,收率60.3%)。
(2)在氮气保护下,向三口烧瓶中加入IM-c-a(50.0g,99.43mmol)、四丁基氟化铵(5.2g,19.89mmol)与二氯甲烷(400mL),室温搅拌24h。反应液经过水洗、分液后,有机相干燥、过滤、减压除去溶剂,所得油状粗品用二氯甲烷/石油醚(体积比1:5)作为洗脱剂经硅胶色谱柱分离提纯得到IM-c-b(9.9g,收率26.9%)。
(3)在氮气保护下,向三口烧瓶中加入IM-c-b(9.5g,mmol)、偶氮二异丁腈(AIBN)(0.08g,0.51mmol)、N-溴代丁二酰亚胺(6.8g,38.45mmol)和四氯化碳(100mL),开启搅拌,并升温至回流,反应8h后停止加热;自然降温至室温后加入100mL去离子水淬灭反应,分出有机相,水洗至中性,分液后进行干燥、过滤、减压蒸馏除去溶剂,所得粗品经硅胶柱分离提纯,二氯甲烷/石油醚作为洗脱机,分别得到一溴代产物IM C1(7.2g,收率62.2%)和二溴代产物IM C2(2.6g,收率19.3%)。
4、化合物的合成
(1)化合物A04的合成
(1)将IMA1(10.8g,25.78mmol)、4-氨基联苯(4.5g,26.55mmol)、三(二亚苄基丙酮)二钯(0.5g,0.52mmol)、2-二环己基膦-2',6'-二甲氧基联苯(0.5g,1.04mmol)和叔丁醇钠(3.7g,38.66mmol)加入甲苯(50mL)中,在氮气保护下加热至108℃,搅拌4h;而后冷却至室温,反应液使用水洗后加入无水硫酸镁干燥,过滤后减压蒸馏除去溶剂,得到黄色固体粗品;再使用甲苯体系对粗品进行重结晶提纯,得到IMA1-N(9.2g,收率64.7%)。
(2)将IMA1-N(8.5g,15.40mmol)、4-溴联苯(3.6g,15.36mmol)、三(二亚苄基丙酮)二钯(0.28g,0.31mmol)、2-二环己基膦-2’,6’-二甲氧基联苯(0.25g,0.61mmol)以及叔丁醇钠(2.2g,23.04mmol)加入甲苯(80mL)中,在氮气保护下加热至108℃,搅拌4h;而后冷却至室温,反应液使用水洗后加入无水硫酸镁干燥,过滤后减压蒸馏除去溶剂,所得粗品用甲苯重结晶提纯,得到白色固体化合物A04(5.1g,收率47.2%),质谱(m/z)=704.3[M+H]+。
采用与化合物A04相同的制备方法制备表3中的化合物,不同之处在于:分别用表3中的中间体替换中间体IMA1,用原料4替换4-氨基联苯,用原料5替换4-溴联苯,其他条件不变;所用物料及产物的结构、最后一步收率和质谱表征结果均列于表3中。
表3
(2)化合物D02的合成
向三口烧瓶中依次加入IMA4(5.0g,11.03mmol)、N-苯基-1-萘胺(4.9g,22.17mmol)、三(二亚苄基丙酮)二钯(0.2g,0.22mmol)、2-二环己基膦-2',6'-二甲氧基联苯(0.22g,0.55mmol)、叔丁醇钠(2.5g,26.46mmol)和甲苯(50mL),氮气保护下加热至108℃,搅拌4h;而后冷却至室温,反应液使用水洗后分液,有机相加入无水硫酸镁干燥,过滤后减压蒸馏除去溶剂;使用甲苯体系对粗品进行重结晶提纯,得到白色固体化合物D02(5.3g,收率48.0%),质谱(m/z)=819.4[M+H]+。
采用与化合物D02相同的方法制备表4中的化合物,不同之处在于:分别用表4中的中间体替换中间体IMA4,用原料6替换N-苯基-1-萘胺,其他条件不变;所用物料及产物的结构、收率和质谱表征结果均列于表4中。
表4
(3)化合物E03的合成
在氮气保护下,将IMA1(8.0g,19.09mmol)、联硼酸频那醇酯(5.8g,22.91mmol)、三(二亚苄基丙酮)二钯(0.35g,0.38mmol)、2-二环己基膦-2',4',6'-三异丙基联苯(0.36g,0.76mmol)以及醋酸钾(3.7g,38.18mmol)、1,4-二氧六环(100mL)加入到反应瓶中,加热至80℃搅拌6h;而后冷却至室温,反应液
水洗至中性,分液后水洗至中性,合并有机相,干燥、过滤、减压除去溶剂;使用乙酸乙酯/石油醚(体积比为1:3)对粗品进行重结晶提纯,得到白色固体IMA1-B(5.2g,收率53.4%)。
在氮气保护下,向反应瓶中加入IMA1-B(5.0g,9.79mmol)、N-[1,1`-联苯]-4-基-N-(4-溴苯肼)-9,9-二甲基-9H-芴-2-胺(5.06g,9.79mmol)、甲苯(60mL)、乙醇(20mL)、水(10mL)和碳酸钾(3.0g,21.65mmol),搅拌加热升温至50℃-60℃,迅速加入四(三苯基膦)钯(0.23g,0.20mmol)和四丁基溴化铵(TBAB)(0.63g,1.95mmol),然后继续升温至70-75℃回流,反应18h。反应完毕,降温,用二氯甲烷萃取,有机相水洗至中性,合并有机相、分液,有机相用无水硫酸镁干燥,过滤,减压蒸馏除去溶剂。用甲苯/石油醚重结晶提纯,烘干得白色固体化合物E03(3.9g,收率48.6%),质谱(m/z)=820.4[M+H]+。
采用与化合物E03相同的方法制备表5中的化合物,不同之处在于:分别用表5中的中间体IM-Xy替换中间体IMA1,用原料7替换N-[1,1`-联苯]-4-基-N-(4-溴苯肼)-9,9-二甲基-9H-芴-2-胺,其他条件不变;所用物料及产物的结构、最后一步收率和质谱表征结果均列于表5中。
表5
化合物核磁数据如表6所示:
表6
有机电致发光器件制备及评估:
实施例1:红色有机电致发光器件
阳极制备:将ITO厚度为的基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸,采用光刻工序,将其制备成具有阴极、阳极以及绝缘层图案的实验基板,利用紫外臭氧以及O2:N2等离子进行表面处理,以清除表面浮渣并提高基板阳极功函数。
在实验基板(阳极)上真空蒸镀的HAT-CN形成空穴注入层(HIL),并且在HAT-CN层上蒸镀NPB,形成的第一空穴传输层(HTL-1)。
在第一空穴传输层上再蒸镀化合物A04,形成厚度为的第二空穴传输层(HTL-2)。
然后在第二空穴传输层上,将RH-1:RD-1以97%:3%的膜厚比进行共同蒸镀,形成了厚度为的有机发光层(红色发光层,R-EML)。
再将ET-10和LiQ以4:6的蒸镀速率比共同蒸镀形成厚度为的电子传输层(ETL),将Yb蒸镀在电子传输层上,形成厚度为的电子注入层(EIL),然后在电子注入层上以1:10的蒸镀速率比真空蒸镀镁和银,形成厚度为的阴极。
最后在阴极上蒸镀的CP-1,形成有机覆盖层(CPL),从而完成红色有机电致发光器件的制造。
实施例2~40:
实施例2~40中,除了在形成第二空穴传输层时分别使用表8中所示的化合物A12~E56替换实施例1中的化合物A04以外,利用与实施例1相同的方法制作有机电致发光器件。
对比例1~4:
在对比例1~4中,采用与实施例1相同的方法制造有机电致发光器件,区别仅在于:分别使用化合物A、B、C、D替换化合物A04。
以上实施例和对比例使用的主要材料结构如表7所示。
表7
对各实施例和对比例制备的器件进行性能测试,其中,IVL(工作电压、电流效率、色坐标)数据是在10mA/cm2电流密度下测试,器件T95寿命在恒定电流密度20mA/cm2下进行测试,器件性能见表8。
表8
由表8可知,使用本申请有机化合物作为第二空穴传输层的实施例1~40制备的有机电致发光器件与对比例1~4的器件相比,各项性能均有所提高。其中,电流效率(Cd/A)至少提高13.5%,寿命(T95)至少提高了16.1%。可见,将本申请的有机化合物用于有机电致发光器件的第二空穴传输层可以显著提升有机电致发光器件的发光效率和T95寿命。
本申请有机化合物的结构中含有环烷基与两个以上的芴平面形成的多螺环结构,使芴平面结构在空间上形成大螺环,可有效提高空穴的迁移率,适合于有机电致发光器件的第二空穴传输层,从而使得由其制备的有机电致发光器件具有低电压、高效率的特征。另外,通过螺环方式将共轭平面组合起来,在空间上也能降低分子间的堆叠,改善材料成膜时的无定形态,使其用于有机电致发光器件时具有更佳的稳定性,因此,与对比例1~4相比,本申请实施例的有机电致发光器件的寿命有明显的提升。更具体地,化合物A螺环部分中具有非芳香性双键,在电场作用下易发生聚合,导致器件特性变差;化合物B芳胺连接于中间苯环上,导致其平面共轭特性变差,进一步导致器件性能也相对较差。
以上详细描述了本申请的优选实施方式,但是,本申请并不限于上述实施方式中的具体细节,在本申
请的技术构思范围内,可以对本申请的技术方案进行多种简单变型,这些简单变型均属于本申请的保护范围。
Claims (13)
- 有机化合物,其具有式1所示的结构:
其中,n和m相同或不同,且各自独立地选自1、2或3;R1、R2、R3和R4相同或不同,且各自独立地选自氘、卤素基团、氰基、碳原子数为1~10的烷基或碳原子数为3~12的三烷基硅基;n1表示R1的个数,且n1选自0、1、2、3或4,当n1大于1时,任意两个R1相同或不同;n2表示R2的个数,且n2选自0、1、2、3或4,当n2大于1时,任意两个R2相同或不同;n3表示R3的个数,且n3选自0、1、2、3或4,当n3大于1时,任意两个R3相同或不同;n4表示R4的个数,且n4选自0、1、2、3或4,当n4大于1时,任意两个R4相同或不同;A、B、C和D相同或不同,分别独立地选自氢或式2所示的基团,且A、B、C、D中至少有一个为式2所示的基团;a表示L的个数,且a选自1或2;Ar1和Ar2相同或不同,且各自独立地选自碳原子数为6~40的取代或未取代的芳基、碳原子数为3~40的取代或未取代的杂芳基;L、L1和L2相同或不同,且各自独立地选自单键、碳原子数为6~30的取代或未取代的亚芳基、碳原子数为3~30的取代或未取代的亚杂芳基;Ar1、Ar2、L、L1和L2中的取代基相同或不同,且各自独立地选自氘、卤素基团、氰基、碳原子数为1~10的烷基、碳原子数为3~12的三烷基硅基、碳原子数为1~10的卤代烷基、碳原子数为3~10的环烷基、碳原子数为6~20的芳基或碳原子数为3~20的杂芳基;任选地,Ar1中的任意两个相邻的取代基形成饱和或不饱和的3~15元环;任选地,Ar2中的任意两个相邻的取代基形成饱和或不饱和的3~15元环。 - 根据权利要求1所述的有机化合物,其中,式1选自以下式I-1~I-3所示结构:
式I-1至I-3中,A、B、C、D、R1、R2、R3、R4、n1、n2、n3和n4的定义同式1。 - 根据权利要求1所述的有机化合物,其中,Ar1和Ar2相同或不同,且各自独立地选自碳原子数为6~25的取代或未取代的芳基、碳原子数为12~25的取代或未取代的杂芳基;可选地,Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1~5的烷基、三甲基硅基、三氟甲基、碳原子数为5~10的环烷基或碳原子数为6~12的芳基;任选地,Ar1中的任意两个相邻的取代基形成苯环或芴环;任选地,Ar2中的任意两个相邻的取代基形成苯环或芴环。
- 根据权利要求1所述的有机化合物,其中,Ar1和Ar2相同或不同,且各自独立地选自取代或未取代的苯基、取代或未取代的萘基、取代或未取代的联苯基、取代或未取代的芴基、取代或未取代的菲基、取代或未取代的三联苯基、取代或未取代的螺二芴基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基;可选地,Ar1和Ar2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、三甲基硅基、三氟甲基、环戊烷、环己烷、苯基、萘基、联苯基、二苯并呋喃基或二苯并噻吩基;任选地,Ar1中的任意两个相邻的取代基形成苯环;任选地,Ar2中的任意两个相邻的取代基形成苯环。
- 根据权利要求1所述的有机化合物,其中,Ar1和Ar2相同或不同,且各自独立地选自以下基团构成的组:
- 根据权利要求1所述的有机化合物,其中,L、L1和L2相同或不同,且各自独立地选自单键、碳原子数为6~20的取代或未取代的亚芳基、碳原子数为12~18的取代或未取代的亚杂芳基;可选地,L、L1和L2中的取代基各自独立地选自氘、氟、氰基、碳原子数为1~5的烷基或碳原子数为6~12的芳基。
- 根据权利要求1所述的有机化合物,其中,L、L1和L2相同或不同,且各自独立地选自单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚芴基、取代或未取代的亚菲基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基;可选地,L、L1和L2中的取代基各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基或萘基。
- 根据权利要求1所述的有机化合物,其中,式1中选自单键或者以下基团构成的组:
可选地,L1和L2各自独立地选自单键或者以下基团构成的组:
- 根据权利要求1所述的有机化合物,其中,R1、R2、R3和R4相同或不同,且各自独立地选自氘、氟、氰基、甲基、乙基、异丙基、叔丁基、苯基或三甲基硅基。
- 根据权利要求1所述的有机化合物,其中,所述有机化合物选自以下化合物所构成的组:
- 电子元件,包括相对设置的阳极和阴极,以及设于所述阳极和所述阴极之间的功能层;所述功能层包含权利要求1~10中任一项所述的有机化合物;可选地,所述电子元件为有机电致发光器件或光电转换器件。
- 根据权利要求11所述的电子元件,其中,所述功能层包括第二空穴传输层,所述第二空穴传输层包含所述有机化合物。
- 电子装置,其包括权利要求11或12所述的电子元件。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211304334.9 | 2022-10-24 | ||
CN202211304334.9A CN115960001B (zh) | 2022-10-24 | 2022-10-24 | 有机化合物及包含其的电子元件和电子装置 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2024087586A1 true WO2024087586A1 (zh) | 2024-05-02 |
Family
ID=87359199
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2023/094055 WO2024087586A1 (zh) | 2022-10-24 | 2023-05-12 | 有机化合物及包含其的电子元件和电子装置 |
Country Status (2)
Country | Link |
---|---|
CN (1) | CN115960001B (zh) |
WO (1) | WO2024087586A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115960001B (zh) * | 2022-10-24 | 2024-04-19 | 陕西莱特光电材料股份有限公司 | 有机化合物及包含其的电子元件和电子装置 |
CN116444467B (zh) * | 2023-06-19 | 2023-10-13 | 吉林奥来德光电材料股份有限公司 | 一种发光辅助材料及其制备方法、有机电致发光器件 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004171986A (ja) * | 2002-11-21 | 2004-06-17 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
CN112745229A (zh) * | 2019-10-31 | 2021-05-04 | 南京高光半导体材料有限公司 | 一种具有优异性能的空穴传输材料及含有该材料的有机电致发光器件 |
CN113717059A (zh) * | 2021-03-12 | 2021-11-30 | 陕西莱特光电材料股份有限公司 | 一种有机化合物及包含其的电子元件和电子装置 |
CN115960001A (zh) * | 2022-10-24 | 2023-04-14 | 陕西莱特光电材料股份有限公司 | 有机化合物及包含其的电子元件和电子装置 |
CN116249365A (zh) * | 2021-12-08 | 2023-06-09 | 三星显示有限公司 | 包括杂环化合物的发光器件和包括发光器件的电子设备 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6998487B2 (en) * | 2001-04-27 | 2006-02-14 | Lg Chem, Ltd. | Double-spiro organic compounds and organic electroluminescent devices using the same |
KR101993129B1 (ko) * | 2013-12-12 | 2019-06-26 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
KR101837804B1 (ko) * | 2015-02-16 | 2018-03-12 | 주식회사 엘지화학 | 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
-
2022
- 2022-10-24 CN CN202211304334.9A patent/CN115960001B/zh active Active
-
2023
- 2023-05-12 WO PCT/CN2023/094055 patent/WO2024087586A1/zh unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004171986A (ja) * | 2002-11-21 | 2004-06-17 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
CN112745229A (zh) * | 2019-10-31 | 2021-05-04 | 南京高光半导体材料有限公司 | 一种具有优异性能的空穴传输材料及含有该材料的有机电致发光器件 |
CN113717059A (zh) * | 2021-03-12 | 2021-11-30 | 陕西莱特光电材料股份有限公司 | 一种有机化合物及包含其的电子元件和电子装置 |
CN116249365A (zh) * | 2021-12-08 | 2023-06-09 | 三星显示有限公司 | 包括杂环化合物的发光器件和包括发光器件的电子设备 |
CN115960001A (zh) * | 2022-10-24 | 2023-04-14 | 陕西莱特光电材料股份有限公司 | 有机化合物及包含其的电子元件和电子装置 |
Also Published As
Publication number | Publication date |
---|---|
CN115960001B (zh) | 2024-04-19 |
CN115960001A (zh) | 2023-04-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2021135207A1 (zh) | 含氮化合物、电子元件和电子装置 | |
WO2021213109A1 (zh) | 一种芳胺化合物、使用其的电子元件及电子装置 | |
CN113501800B (zh) | 有机电致发光材料、电子元件及电子装置 | |
WO2022262365A1 (zh) | 有机化合物及包含其的电子元件和电子装置 | |
WO2022213905A1 (zh) | 有机化合物以及使用其的电子元件和电子装置 | |
CN113717059B (zh) | 一种有机化合物及包含其的电子元件和电子装置 | |
WO2024087586A1 (zh) | 有机化合物及包含其的电子元件和电子装置 | |
WO2021082504A1 (zh) | 含氮化合物、电子元件和电子装置 | |
CN113200992B (zh) | 含氮化合物、有机电致发光器件和电子装置 | |
WO2022170831A1 (zh) | 有机电致发光材料、电子元件和电子装置 | |
WO2022089093A1 (zh) | 含氮化合物、电子元件和电子装置 | |
CN114989069B (zh) | 含氮化合物和电子元件及电子装置 | |
WO2022206389A1 (zh) | 含氮化合物及包含其的电子元件和电子装置 | |
WO2022068292A1 (zh) | 一种有机化合物以及使用其的电子元件和电子装置 | |
CN114075117A (zh) | 一种有机化合物以及使用其的电子元件和电子装置 | |
WO2024037073A1 (zh) | 含氮化合物、电子元件和电子装置 | |
WO2023179094A1 (zh) | 有机化合物及包含其的电子元件和电子装置 | |
CN113896720B (zh) | 有机化合物、电子元件及电子装置 | |
CN114335399A (zh) | 有机电致发光器件及包括其的电子装置 | |
CN113421980A (zh) | 有机电致发光器件及包含其的电子装置 | |
WO2024152591A1 (zh) | 有机化合物及包含其的电子元件和电子装置 | |
WO2024148883A1 (zh) | 有机化合物、组合物、有机电致发光器件及电子装置 | |
WO2024131005A1 (zh) | 有机化合物、有机电致发光器件和电子装置 | |
CN113493455B (zh) | 有机化合物、电子元件和电子装置 | |
WO2024148882A1 (zh) | 有机化合物、组合物、有机电致发光器件及电子装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 23881180 Country of ref document: EP Kind code of ref document: A1 |