CN114075115A - Amine compound and organic electroluminescent device containing same - Google Patents
Amine compound and organic electroluminescent device containing same Download PDFInfo
- Publication number
- CN114075115A CN114075115A CN202010845559.XA CN202010845559A CN114075115A CN 114075115 A CN114075115 A CN 114075115A CN 202010845559 A CN202010845559 A CN 202010845559A CN 114075115 A CN114075115 A CN 114075115A
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- CN
- China
- Prior art keywords
- group
- atom
- naphthyl
- unsubstituted
- substituted
- Prior art date
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- -1 Amine compound Chemical class 0.000 title claims abstract description 71
- 239000000463 material Substances 0.000 claims abstract description 96
- 230000005525 hole transport Effects 0.000 claims abstract description 41
- 238000002347 injection Methods 0.000 claims description 48
- 239000007924 injection Substances 0.000 claims description 48
- 125000001624 naphthyl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 28
- 230000000903 blocking effect Effects 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 16
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 16
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 16
- 150000001975 deuterium Chemical group 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052722 tritium Inorganic materials 0.000 claims description 16
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 14
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
- 125000004957 naphthylene group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 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 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
- 239000004305 biphenyl Substances 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000010410 layer Substances 0.000 description 150
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 21
- 239000000758 substrate Substances 0.000 description 20
- 239000010408 film Substances 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 17
- 238000004770 highest occupied molecular orbital Methods 0.000 description 15
- 239000011368 organic material Substances 0.000 description 14
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000007738 vacuum evaporation Methods 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides 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
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 2
- 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229910052771 Terbium Inorganic materials 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052775 Thulium Inorganic materials 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group 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 2
- 230000005284 excitation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052735 hafnium Inorganic materials 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 150000002979 perylenes Chemical group 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- OMDTUSYJJFBYMG-UHFFFAOYSA-N 2,4-bis(9,9-dimethylfluoren-2-yl)-6-naphthalen-2-yl-1,3,5-triazine Chemical compound C1=CC=C2C(C)(C)C3=CC(C=4N=C(N=C(N=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 OMDTUSYJJFBYMG-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical class NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
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- 101100072645 Arabidopsis thaliana IPS3 gene Proteins 0.000 description 1
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 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
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
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- 101710110702 Probable chorismate pyruvate-lyase 1 Proteins 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
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- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
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- 229910052784 alkaline earth metal 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
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- 239000010405 anode material Substances 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
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- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
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- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
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- 159000000006 cesium salts Chemical class 0.000 description 1
- AYTVLULEEPNWAX-UHFFFAOYSA-N cesium;azide Chemical compound [Cs+].[N-]=[N+]=[N-] AYTVLULEEPNWAX-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
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- 239000010949 copper Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 150000002220 fluorenes Chemical group 0.000 description 1
- 125000005567 fluorenylene group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 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
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
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- 238000010030 laminating Methods 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- MESMXXUBQDBBSR-UHFFFAOYSA-N n,9-diphenyl-n-[4-[4-(n-(9-phenylcarbazol-3-yl)anilino)phenyl]phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 MESMXXUBQDBBSR-UHFFFAOYSA-N 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000005564 oxazolylene group Chemical group 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=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
- JPHSWUBDHJSNLZ-UHFFFAOYSA-N phenyl-[2-(2-phenylphosphanylphenoxy)phenyl]phosphane Chemical compound C=1C=CC=C(PC=2C=CC=CC=2)C=1OC1=CC=CC=C1PC1=CC=CC=C1 JPHSWUBDHJSNLZ-UHFFFAOYSA-N 0.000 description 1
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- 229920003023 plastic Polymers 0.000 description 1
- 229920000767 polyaniline 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
- 229960003975 potassium Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000005550 pyrazinylene group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002210 silicon-based material Chemical class 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005559 triazolylene group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
Images
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
- C07C211/57—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
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an amine compound with a general formula (1) as defined in the specification, a preparation method thereof and application thereof as a hole transport material in an organic electroluminescent device. The invention also relates to an organic electroluminescent device which sequentially comprises an anode, a hole transport region, a luminescent region, an electron transport region and a cathode from bottom to top, wherein the hole transport region comprises the amine compound of the general formula (1) as described in the specification, and a display device comprising the organic electroluminescent device.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to an amine compound, a preparation method thereof, an application of the amine compound as a hole transport material in an organic electroluminescent device, the organic electroluminescent device containing the amine compound, and a display device containing the organic electroluminescent device.
Background
Carriers (holes and electrons) in an organic electroluminescent device (OLED) are injected into the device from two electrodes of the device respectively under the driving of an electric field, and meet recombination to emit light in an organic light emitting layer. High performance organic electroluminescent devices require various organic functional materials to have good photoelectric properties. For example, as a charge transport material, it is required to have good carrier mobility. The hole injection layer material and the hole transport layer material used in the existing organic electroluminescent device have relatively weak injection and transport characteristics, and the hole injection and transport rate is not matched with the electron injection and transport rate, so that the composite region has large deviation, and the stability of the device is not facilitated. In addition, reasonable energy level matching between the hole injection layer material and the hole transport layer material is an important factor for improving the efficiency and the service life of the device, and therefore, how to adjust the balance between holes and electrons and adjust the recombination region is an important subject in the field.
Blue organic electroluminescent devices are always soft ribs in the development of full-color OLEDs, and the efficiency, the service life and other properties of blue light devices are difficult to be comprehensively improved at present, so that how to improve the properties of the blue light devices is still a crucial problem and challenge in the field. Most of blue host materials currently used in the market are electron-biased hosts, and therefore, in order to adjust the carrier balance of the light-emitting layer, a hole-transporting material is required to have excellent hole-transporting performance. The better the hole injection and transmission, the more the composite region will shift to the side far away from the electron blocking layer, so as to far away from the interface to emit light, thus improving the performance of the device and prolonging the service life. Therefore, the hole transport region material is required to have high hole injection property and high hole mobility.
Since the hole transport material has a thick film thickness, the heat resistance and amorphousness of the material have a crucial influence on the lifetime of the device. Materials with poor heat resistance are easy to decompose in the evaporation process, pollute the evaporation cavity and damage the service life of devices; the material with poor film phase stability can crystallize in the use process of the device, and the service life of the device is reduced. Therefore, the hole transport material is required to have high film phase stability and decomposition temperature during use. However, the development of materials for stable and effective organic material layers for organic electroluminescent devices has not been sufficiently realized. Therefore, there is a continuous need to develop a new material to better meet the performance requirements of the organic electroluminescent device.
Disclosure of Invention
In order to solve the problems, the organic electroluminescent device is prepared by combining materials with excellent hole and electron injection/transmission performance, film stability and weather resistance, the organic electroluminescent device is beneficial to improving the recombination efficiency of electrons and holes and the utilization rate of excitons, and the obtained device has low driving voltage and long service life.
Accordingly, the present inventors have developed a novel amine compound in which a naphthodiphenylfluorene group or a spirofluorene group employs a substituted or unsubstituted aryl group as a bridging group, so that the compound of the present invention has excellent hole transporting ability, film phase stability and weather resistance. Further, the present inventors have found that when the amine compound of the present invention is used to form a hole transport layer of an organic electroluminescent device, effects such as reduction in device driving voltage and prolongation of lifetime can be exhibited.
It is therefore an object of the present invention to provide a novel amine compound having the following general formula (1):
wherein
n, m each independently represent a number 0,1 or 2, and m + n is 2 or 3;
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b independently represents phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenyl or terphenyl;
p and q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group;
ar represents one of the following groups;
o, c, a, b each independently represent the number 1 or 2;
R6to R9Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a naphthyl group, a biphenylyl group or an adamantyl group;
L、L1each independently represents phenylene, naphthylene or biphenylene,
L2represents a single bond, phenylene, naphthylene or biphenylene.
Another object of the present invention is to provide a process for the preparation of the amine compounds of the general formula (1).
Another object of the present invention is the use of the amine compounds of the general formula (1) as hole transport materials in organic electroluminescent devices.
It is another object of the present invention to provide an organic electroluminescent device having improved luminous efficiency and lifetime, which comprises, in order from bottom to top, an anode, a hole transporting region, a light emitting region, an electron transporting region and a cathode, wherein the hole transporting region comprises the amine compound of formula (1) as described in the present invention.
It is also an object of the present invention to provide a full color display apparatus including three pixels of red, green and blue, the full color display apparatus including the organic electroluminescent device of the present invention.
Advantageous effects
In the amine compound, the naphtho-diphenyl fluorene group or the spirofluorene group adopts substituted or unsubstituted aryl as a bridging group, so that the compound has excellent hole migration capability, and the fluorene group has a relatively shallow HOMO energy level, can form ohmic contact with an anode and forms a complete CT state under the condition of a lower P doping ratio, thereby effectively avoiding Cross-talk risk (adjacent green light or red light is lightened in the process of lightening blue light under low current density).
In addition, the amine compound of the present invention has a higher glass transition temperature, excellent film phase stability and excellent high temperature weather resistance because the fluorenyl group is a relatively large rigid group, so that the device is not aged or crystallized by heat generated during the lighting process.
In the organic electroluminescent device of the present invention, the hole transport region contains the amine compound as described above, and since it has a strong hole injection transport ability and a suitable energy level, holes can be efficiently transported and injected into the light emitting layer, and high efficiency light emission at a low driving voltage of the organic electroluminescent device can be achieved.
In addition, the amine compound is combined with the nitrogen heterocyclic electron transport material, so that electrons and holes are in an optimal balance state, and the amine compound has higher efficiency and excellent service life, especially the high-temperature service life of a device.
Drawings
Fig. 1 schematically shows a cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
1 represents an anode; 10 denotes a hole transport region, 2 denotes a hole injection layer, 3 denotes a hole transport layer, and 4 denotes an electron blocking layer; 5 denotes a light emitting region; 20 denotes an electron transport region, 6 denotes an electron transport layer, and 7 denotes an electron injection layer; 8 is represented as a cathode; 9 denotes a cover layer; and 30 an organic light emitting diode.
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are merely exemplary, and the present invention is not limited thereto and is defined by the scope of the claims.
In the present invention, unless otherwise specified, all operations are carried out under ambient temperature and pressure conditions.
In the present invention, unless otherwise specified, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule. In addition, the "difference in HOMO energy levels" and "difference in LUMO energy levels" referred to in the present specification mean a difference in absolute value of each energy value. Further, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between the energy levels is also a comparison of the magnitude of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level is, the lower the energy of the energy level is.
In the present invention, when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Like reference numerals refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, and other structures, "upper", "lower", "top", and "bottom" and the like used to indicate orientation only indicate orientation in a certain specific state, and do not mean that the related structures can exist only in the orientation; conversely, if the structure is repositioned, e.g., inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of the electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is further from the substrate is the "top" side.
In this specification, the term "substituted" means that one or more hydrogen atoms on the designated atom or group are replaced with the designated group, provided that the designated atom's normal valency is not exceeded in the present case.
In this specificationIn the book, the term "C6-C30Aryl "refers to a fully unsaturated monocyclic, polycyclic or fused polycyclic (i.e., rings that share a pair of adjacent carbon atoms) system having 6 to 30 ring carbon atoms.
In this specification, the term "C5-C30Heterocyclyl "refers to a saturated, partially saturated, or fully unsaturated cyclic group having 5 to 30 ring carbon atoms and containing at least one heteroatom selected from N, O and S, including but not limited to heteroaryl, heterocycloalkyl, fused rings, or combinations thereof. When the heterocyclyl is a fused ring, each or all of the rings of the heterocyclyl may contain at least one heteroatom.
More precisely, substituted or unsubstituted C6-C30Aryl and/or substituted or unsubstituted C5-C30The heterocyclic group means a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, a substituted or unsubstituted m-terphenylyl group, a substituted or unsubstituted terphenylyl group
A group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, Substituted or unsubstitutedA quinazolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted fluorene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a combination thereof, or a fused ring of a combination of the foregoing groups, but is not limited thereto.
In the present specification, substituted or unsubstituted C6-C30Arylene or substituted or unsubstituted C5-C30Heterocyclylene means, respectively, a substituted or unsubstituted C as defined above and having two linking groups6-C30Aryl or substituted or unsubstituted C5-C30A heterocyclic group such as a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted tetracylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted paratriphenylene group, a substituted or unsubstituted metatriphenylene group, a substituted or unsubstituted phenylene group
A group, a substituted or unsubstituted triphenylene-biphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted pyrrolylene group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolylene group, a substituted or unsubstituted oxazolylene group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted pyrazinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted benzofuranylene groupThienyl, substituted or unsubstituted benzimidazolylene, substituted or unsubstituted indolyl, substituted or unsubstituted quinolylene, substituted or unsubstituted isoquinolylene, substituted or unsubstituted quinazolinylene, substituted or unsubstituted quinolylene, substituted or unsubstituted naphthyridine, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, combinations thereof or combinations thereof.
In this specification, the hole characteristics refer to characteristics that are capable of supplying electrons when an electric field is applied and holes formed in the anode are easily injected into and transported in the light emitting layer due to the conductive characteristics according to the Highest Occupied Molecular Orbital (HOMO) level.
In the present specification, the electron characteristics refer to characteristics that can accept electrons when an electric field is applied and electrons formed in the cathode are easily injected into and transported in the light emitting layer due to the conductive characteristics according to the Lowest Unoccupied Molecular Orbital (LUMO) level.
Amine compounds of the general formula (1)
The invention provides an amine compound shown as a general formula (1):
wherein
n, m each independently represent a number 0,1 or 2, and m + n is 2 or 3;
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b independently represents phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenyl or terphenyl;
p and q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group;
ar represents one of the following groups;
o, c, a, b each independently represent the number 1 or 2;
R6to R9Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a naphthyl group, a biphenylyl group or an adamantyl group;
L、L1each independently represents phenylene, naphthylene or biphenylene,
L2represents a single bond, phenylene, naphthylene or biphenylene.
In a preferred embodiment of the present invention,
m + n is 2, and Ar represents formula (2), formula (4), or formula (5);
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b independently represents phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenyl or terphenyl;
p, q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group;
o, a, b represent the numbers 1 or 2;
L1represented by phenylene, naphthylene or biphenylene,
L2represents a single bond, phenylene, naphthylene or biphenylene;
R6、R8to R9Expressed as a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a naphthyl group, a biphenylyl group or an adamantyl group.
In another preferred embodiment of the present invention,
m represents a number 1 or 2, and m + n ═ 2;
ar is represented by formula (3);
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b is respectively and independently phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenyl or terphenyl;
p, q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group;
R7represented by a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a naphthyl group, a biphenylyl group or an adamantyl group;
l represents phenylene, naphthylene or biphenylene.
According to a further preferred embodiment of the present invention,
m + n is 3, and Ar represents formula (6);
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b independently represents phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenylOr a terphenyl group;
p, q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group.
Preferred specific examples of the amine compound of the general formula (1) of the present invention include the following compounds, but are not limited thereto:
in a more preferred embodiment of the present invention, the amine compound of the general formula (1) may be selected from any one of the following compounds:
process for preparing amines of the general formula (1)
The amine compounds of general formula (1) of the present invention can be prepared using methods known in the art. The synthetic route used starts from commercially available or readily preparable haloaryldiphenylfluorenes and arylamines for coupling reactions to give arylamine-substituted aryldiphenylfluorenes, which are subsequently coupled with dihalogenated or trihaloaromatic compounds, the products optionally being subjected to Buchwald-Hartwig amination reactions to give amine compounds of the general formula (1). The desired dihalo-or trihaloaromatic compounds are commercially available or may be obtained by methods known to those skilled in the art. The conditions for conducting the Buchwald-Hartwig amination reaction are known to those skilled in the art.
The coupling reaction for preparing the amine compound of formula (1) can be carried out in the presence of a suitable palladium catalyst, a phosphine ligand and a base. The reaction can be carried out using palladium complexes which are conventional in the art for catalyzing coupling reactions. An exemplary but non-limiting palladium complex is, for example, Pd (PPh)3)4、Pd(dppf)Cl2、Pd(PPh3)2Cl2、Pd(OAc)2Or Pd2(dba)3Preferably Pd2(dba)3。
Suitable bases are inorganic or organic bases commonly used in the art for coupling reactions. These preferably include: alkali metal hydroxides such as lithium hydroxide, sodium hydroxide or potassium hydroxide; alkali metal carbonates or alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate or cesium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal alkoxides, such as sodium or potassium methoxide or tert-butoxide or potassium tert-butoxide; amides, such as sodium amide, lithium bis (trimethylsilyl) amide, sodium bis (trimethylsilyl) amide, or potassium bis (trimethylsilyl) amide or lithium diisopropylamide; or organic amines, e.g. triethylamine, N-methylmorpholine, N-methylpiperidine, N-diisopropylethylamine, pyridine, 1, 5-diazabicyclo [4.3.0 ]]Non-5-ene (DBN), 1, 8-diazabicyclo [5.4.0]Undec-7-ene (DBU) or 1, 4-diazabicyclo [2.2.2]Octane
Or potassium phosphate. Preference is given to using sodium tert-butoxide, potassium tert-butoxide or sodium carbonate.
Suitable phosphine ligands for the coupling reaction are, for example, triphenylphosphine, (2-biphenyl) di-tert-butylphosphine, 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (SPHOS), dicyclohexyl [2',4',6' -tris (1-methylethyl) biphenyl-2-yl ] phosphine (XPHOS), bis (2-phenylphosphinophenyl) ether (DPEphos), 4, 5-bis (diphenylphosphino) -9, 9-dimethylxanthene (Xantphos).
The reaction of the present invention is also carried out in a suitable solvent. The solvents are in principle all organic solvents which are inert under the reaction conditions. Examples include, but are not limited to: benzene, for example toluene, xylene, preferably toluene.
Organic electroluminescent device
The present invention provides an organic electroluminescent device using an amine compound of the general formula (1).
In one exemplary embodiment of the present invention, an organic electroluminescent device may include an anode, a hole transport region, a light emitting region, an electron transport region, and a cathode. The organic electroluminescent device may be manufactured by conventional methods and materials for manufacturing organic electroluminescent devices, except that the amine-based compound of formula (1) is used in the organic electroluminescent device.
The organic electroluminescent device of the present invention may be a bottom emission organic electroluminescent device, a top emission organic electroluminescent device, and a stacked organic electroluminescent device, which is not particularly limited.
In the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices may also be used. Examples thereof are transparent substrates such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; a flexible Polyimide (PI) film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. The direction of use varies depending on the nature of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
Anode
Preferably, the anode may be formed on the substrate. In the present invention, the anode and the cathode are opposed to each other. The anode may be made of a conductor, such as a metal, metal oxide, and/or conductive polymer, having a high work function to aid hole injection. The anode may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, silver, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals with metal oxides, e.g. ZnO with Al or SnO2And Sb, or ITO and Ag; conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1, 2-dioxy) thiophene) (PEDOT), polypyrrole, and polyaniline, but are not limited thereto. The thickness of the anode depends on the material used and is typically 50-500nm, preferably 70-300nm, and more preferably 100-200 nm.
Cathode electrode
The cathode may be made of a conductor having a lower work function to aid in electron injection, and may be, for example, a metal oxide, and/or a conductive polymer. The cathode may be, for example, a metal or alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, and combinations thereof, particularly a magnesium aluminum alloy in a mass ratio of 1: 1; materials of multilayer structure, e.g. LiF/Al, Li2O/Al, LiF/Ca and BaF2But not limited thereto,/Ca. The thickness of the cathode depends on the material used and is generally from 10 to 50nm, preferably from 15 to 20 nm.
Light emitting area
In the present invention, the light emitting region may be disposed between the anode and the cathode, and may include at least one host material and at least one guest material. As the host material and the guest material of the light emitting region of the organic electroluminescent device of the present invention, light emitting layer materials for organic electroluminescent devices known in the art can be used. The host material may be, for example, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative, or 4,4' -bis (9-Carbazolyl) Biphenyl (CBP). Preferably, the host material may comprise anthracene groups. The guest material may be, for example, quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives or aminostyrene derivatives.
In a preferred embodiment of the present invention, one or two host material compounds are contained in the light-emitting region.
In a preferred embodiment of the present invention, two host material compounds are contained in the light emitting region, and the two host material compounds form an exciplex.
In a preferred embodiment of the present invention, the host material of the light emitting region used is selected from one or more of the following compounds BH1-BH 24:
in the present invention, the light emitting region may include a phosphorescent or fluorescent guest material to improve the fluorescent or phosphorescent characteristics of the organic electroluminescent device. Specific examples of phosphorescent guest materials include metal complexes of iridium, platinum, and the like. For example, Ir (ppy)3[ fac-tris (2-phenylpyridine) iridium]And the like, blue phosphorescent materials such as FIrpic and FIr6, and red phosphorescent materials such as Btp2Ir (acac). For the fluorescent guest material, those generally used in the art can be used. In a preferred embodiment of the present invention, the guest material of the light-emitting film layer used is selected from one of the following compounds BD-1 to BD-23:
in the light emitting region of the present invention, the ratio of the host material to the guest material is used in a range of 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 by mass.
In the light emitting region of the present invention, a host material may also be mixed with a small amount of a dopant to produce a material that emits light, which may be an organic compound or a metal complex such as Al that emits fluorescence by singlet excitation; or a material such as a metal complex that emits light by multiple-state excitation into a triplet state or more. The dopant may be, for example, an inorganic compound, an organic compound, or an organic/inorganic compound, and one or more species thereof may be used.
Examples of dopants may be organometallic compounds comprising Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The dopant may be, for example, a compound represented by the following formula (Z), but is not limited thereto:
L2MX formula (Z)
Wherein the content of the first and second substances,
m is a metal, and M is a metal,
L2identical or different from X and is a ligand which forms a complex with M.
In one embodiment of the invention, M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L2And X can be, for example, a bidentate ligand.
The thickness of the light emitting region of the present invention may be 10 to 50nm, preferably 15 to 30nm, but the thickness is not limited to this range.
Hole transport region
In the organic electroluminescent device of the present invention, a hole transport region is provided between the anode and the light emitting region, and includes a hole injection layer, a hole transport layer, and an electron blocking layer.
Hole injection layer
The hole injection material used in the hole injection layer (also referred to as an anode interface buffer layer) is a material that can sufficiently accept holes from the anode at a low voltage, and the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. According to the organic electroluminescent device of the present invention, the hole injection layer contains an amine compound of the general formula (1). In a preferred embodiment, the hole injection layer is a mixed film layer of the amine compound of the general formula (1) and the P-type dopant material. In order to smoothly inject holes from the anode into the organic film layer, the HOMO level of the amine compound of formula (1) must have a certain characteristic with the P-type dopant material, and it is expected that the generation of a charge transfer state between the amine compound of formula (1) and the dopant material is achieved, and ohmic contact between the hole injection layer and the anode is achieved, thereby achieving efficient injection of holes from the electrode to the hole injection layer. This feature is summarized as: the difference between the HOMO energy level of the amine compound in the general formula (1) and the LUMO energy level of the P-type doping material is less than or equal to 0.4 eV. Therefore, for amine compounds of general formula (1) with different HOMO levels, different P-type doping materials need to be selected and matched with the amine compounds, so that ohmic contact of an interface can be realized, and a hole injection effect is improved.
Preferably, the P-type doping material is a compound having charge conductivity selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or a cyclopropane derivative, such as 4,4',4 "- ((1E,1' E, 1" E) -cyclopropane-1, 2, 3-trimethylenetri (cyanoformylidene)) tris (2,3,5, 6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
Further preferably, the P-type doping material used is selected from any one of the following compounds HI-1 to HI-10:
in one embodiment of the present invention, the amine compound of the general formula (1) and the P-type dopant material are used in a ratio of 99:1 to 95:5, preferably 99:1 to 97:3, on a mass basis.
The thickness of the hole injection layer of the present invention may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Hole transport layer
In the organic electroluminescent device of the present invention, the hole transport layer may be disposed on the hole injection layer. The hole transport material is suitably a material having a high hole mobility, which can accept holes from the anode or the hole injection layer and transport the holes into the light-emitting layer. In an embodiment of the present invention, the hole transport layer contains an amine compound described by general formula (1). In a preferred embodiment, the hole transport layer contains the same amine compound described by the general formula (1) as the hole injection layer.
The thickness of the hole transport layer of the present invention may be 80-200nm, preferably 100-150nm, but the thickness is not limited to this range.
Electron blocking layer
In the organic electroluminescent device of the present invention, the electron blocking layer may be disposed between the hole transport layer and the light emitting layer, and particularly, contacts the light emitting layer. The electron blocking layer is provided to contact the light emitting layer, and thus, hole transfer at the interface of the light emitting layer and the hole transport layer can be precisely controlled.
In one embodiment of the invention, the HOMO level of the electron blocking layer is between 5.50-5.85eV, preferably between 5.55-5.75eV, and more preferably between 5.60-5.75 eV.
In a preferred embodiment of the present invention, the electron blocking layer material is a carbazole aromatic amine derivative.
The thickness of the electron blocking layer of the present invention may be 5 to 20nm, preferably 8 to 15nm, but the thickness is not limited to this range.
Electron transport region
In the organic electroluminescent device of the present invention, the electron transport region is disposed between the light emitting region and the cathode, and includes an electron transport layer and an electron injection layer, but is not limited thereto.
Electron injection layer
The electron injection layer may be disposed between the electron transport layer and the cathode. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. Preferably, the electron injection layer material is an N-type metal material. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
Electron transport layer
The electron transport layer may be disposed over the light emitting film layer or, if present, the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, an electron transport layer material for organic electroluminescent devices known in the art, for example, in Alq, can be used3Metal complexes of hydroxyquinoline derivatives represented by BAlq and LiQ, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS number: 1459162-51-6), 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]Imidazole derivatives such as imidazole (CAS number: 561064-11-7, commonly known as LG201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, nitrogen heterocyclic compounds, and the like.
Preferably, the electron transport layer comprises a nitrogen heterocyclic compound of general formula (7):
wherein
Ar1、Ar2And Ar3Independently of one another, represents substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms5-C30Heterocyclyl, said heteroatoms being independently from each other selected from N, O or S;
l represents substituted or unsubstituted C6-C30Arylene radical, substituted or unsubstituted C containing one or more hetero atoms5-C30(ii) heterocyclylene, each of said heteroatoms being independently selected from N, O or S;
n represents 1 or 2;
X1、X2、X3independently of one another, N or CH, with the proviso that X1、X2、X3At least one group in (a) represents N.
Preferably, the nitrogen heterocyclic compound of the general formula (7) is represented by the general formula (7-1):
wherein Ar is1、Ar2、Ar3、X1、X2、X3And L are each as defined above.
In a preferred embodiment of the present invention, the electron transport layer comprises any one selected from the compounds of the following formula (7):
in a more preferred embodiment of the present invention, the electron transport layer comprises any one selected from the group consisting of compounds of the following formula (7):
further preferably, the electron transport layer is a mixed film layer of the compound of formula (7) and LiQ, wherein the mass ratio of the compound of formula (7) and LiQ is 50: 50.
The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, and more preferably 25 to 45nm, but the thickness is not limited to this range.
Covering layer
In order to improve the light extraction efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be added on the cathode of the device. According to the principle of optical absorption and refraction, the CPL cover layer material should have a higher refractive index as well as a better refractive index, and the absorption coefficient should be smaller as well. Any material known in the art may be used as the CPL layer material, such as Alq3, or N4, N4' -diphenyl-N4, N4' -bis (9-phenyl-3-carbazolyl) biphenyl-4, 4' -diamine. The CPL capping layer is typically 5-300nm, preferably 20-100nm and more preferably 40-80nm thick.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layers of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.
Hereinafter, an organic electroluminescent device according to an embodiment of the present invention is described.
The organic electroluminescent device may be any element that converts electrical energy into light energy or converts light energy into electrical energy without particular limitation, and may be, for example, an organic electroluminescent device, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum. Herein, the organic light emitting diode is described as one example of the organic electroluminescent device (but the present invention is not limited thereto), and may be applied to other organic electroluminescent devices in the same manner.
In the drawings, the thickness of layers, films, substrates, regions, etc. are exaggerated for clarity. Like reference numerals refer to like elements throughout the specification. It will be understood that when an element such as a layer, film, region, or substrate is referred to as being "on" another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
Fig. 1 is a schematic cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.
Referring to fig. 1, an organic light emitting diode 30 according to an embodiment of the present invention includes an anode 1 and a cathode 8 facing each other, a hole transport region 10, a light emitting region 5, and an electron transport region 20 sequentially disposed between the anode 1 and the cathode 8, and a capping layer 9 disposed over the cathode, wherein the hole transport region 10 includes a hole injection layer 2, a hole transport layer 3, and an electron blocking layer 4, and the electron transport region 20 includes an electron transport layer 6 and an electron injection layer 7.
The present invention also relates to a method of preparing an organic electroluminescent device comprising sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer and a cathode, and optionally a capping layer, on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, LITI, or the like may be used, but are not limited thereto. In the present invention, it is preferable that the respective layers are formed by a vacuum evaporation method. The individual process conditions in the vacuum evaporation process can be routinely selected by the person skilled in the art according to the actual requirements.
The material for forming each layer according to the present invention may be used as a single layer by forming a film alone, may be used as a single layer by forming a film in admixture with another material, or may be used as a laminated structure of layers formed alone, layers formed in admixture with each other, or a laminated structure of layers formed alone and layers formed in admixture with each other.
The invention also relates to a full-color display device, in particular a flat panel display device, having three pixels of red, green and blue, comprising the organic electroluminescent device of the invention. The display device may further include at least one thin film transistor. The thin film transistor may include a gate electrode, source and drain electrodes, a gate insulating layer, and an active layer, wherein one of the source and drain electrodes may be electrically connected to an anode of the organic electroluminescent device. The active layer may include crystalline silicon, amorphous silicon, an organic semiconductor, or an oxide semiconductor, but is not limited thereto.
Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used in a generic and descriptive sense only and not for purposes of limitation. In some instances, features, characteristics and/or elements described in connection with a particular embodiment may be used alone or in combination with features, characteristics and/or elements described in connection with other embodiments, unless specifically indicated otherwise, as will be apparent to one of ordinary skill in the art upon submission of the present application. Accordingly, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
Examples
Unless otherwise indicated, various materials used in the following examples and comparative examples are commercially available or may be obtained by methods known to those skilled in the art.
Preparation of the Compound of formula (1)
Example 1: synthesis of Compound 1
A250 ml three-necked flask was charged with 0.01mol of the raw material A-1, 0.01mol under a nitrogen gas atmosphere2mol of starting material B-1, 0.03mol of potassium tert-butoxide, 1X 10-4mol tris (dibenzylideneacetone) dipalladium Pd2(dba)3，1×10-4mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, and a sample of the plaque taken, indicating completion of the reaction. Naturally cooling, filtering, rotatably evaporating the filtrate, and passing through a silica gel column (silica gel 100 meshes and 200 meshes, and the eluent: chloroform: n-hexane: 30:70 (volume ratio)) to obtain an intermediate A-1. Elemental analysis Structure (molecular formula C)31H21N): theoretical value C91.37; h5.19; n3.44; test values are: c91.30; h5.24; and N3.46. MS (M/z) (M +): theoretical value is 407.17, found 407.39.
A250 ml three-neck flask is charged with 0.01mol of raw material C-1, 0.024mol of intermediate A-1, 0.03mol of potassium tert-butoxide, 1X 10 mol under the atmosphere of nitrogen-4mol tris (dibenzylideneacetone) dipalladium Pd2(dba)3，1×10-4mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, and a sample of the plaque taken, indicating completion of the reaction. Naturally cooling, filtering, rotatably evaporating the filtrate, and passing through a silica gel column (silica gel 100-200 meshes, eluent: chloroform: n-hexane: 30:70 (volume ratio)) to obtain the target compound 1. Elemental analysis Structure (molecular formula C)78H50N2): theoretical value C92.28; h4.96; n2.76; test values are: c92.25; h4.97; 2.78. MS (M/z) (M +): theoretical value is 1014.40, found 1014.29.
1H NMR (400MHz, chloroform-d) Δ 7.97-7.89 (m,1H), 7.89-7.77 (m,7H), 7.67-7.57 (m,5H),7.52(td,1H), 7.44-7.21 (m,19H),7.18(dd,3H), 7.15-6.97 (m,12H),6.77(dd, 2H).
Example 2: synthesis of Compound 155
A250 ml three-necked flask was charged with 0.01mol of the raw material A-1, 0.012mol of the raw material B-1, 0.03mol of potassium tert-butoxide, and 1X 10 in a nitrogen atmosphere-4mol tris (dibenzylideneacetone) dipalladium Pd2(dba)3，1×10-4mol triphenylphosphine, 150ml toluene, heating reflux 12hAt this time, the spot plate was sampled, indicating that the reaction was complete. Naturally cooling, filtering, rotatably evaporating the filtrate, and passing through a silica gel column (silica gel 100 meshes and 200 meshes, and the eluent: chloroform: n-hexane: 30:70 (volume ratio)) to obtain an intermediate A-1. Elemental analysis Structure (molecular formula C)31H21N): theoretical value C91.37; h5.19; n3.44; test values are: c91.30; h5.24; and N3.46. MS (M/z) (M +): theoretical value is 407.17, found 407.39.
A250 ml three-necked flask was charged with 0.02mol of intermediate A-1, 0.012mol of raw material C-2, 0.03mol of potassium tert-butoxide, 1X 10 in a nitrogen-purged atmosphere-4mol tris (dibenzylideneacetone) dipalladium Pd2(dba)3，1×10-4mol triphenylphosphine, 150ml toluene, heated to reflux for 12 hours, and a sample of the plaque taken, indicating completion of the reaction. Naturally cooling, filtering, rotatably evaporating the filtrate, and passing through a silica gel column (silica gel 100 meshes and 200 meshes, and the eluent: chloroform: n-hexane: 30:70 (volume ratio)) to obtain an intermediate B-1. Elemental analysis Structure (molecular formula C)68H43ClN2): theoretical value C88.44; h4.69; cl 3.84; n3.03; test values are: c88.41; h4.67; cl 3.88; and N3.05. MS (M/z) (M +): theoretical value is 922.31, found 922.47.
Adding 0.01mol of intermediate B-1, 0.012mol of raw material D-1, 0.02mol of sodium carbonate and 150ml of toluene into a 250ml three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 1X 10-4mol tetrakis (triphenylphosphine) palladium Pd (pph)3)4The reaction was heated to 105 ℃ and refluxed for 24 hours, and a sample was taken from the plate to show that no chloride remained and the reaction was complete. Naturally cooling to room temperature, filtering, performing reduced pressure rotary evaporation on the filtrate (-0.09MPa, 85 ℃), and passing through a neutral silica gel column (silica gel 100 meshes and 200 meshes, eluent: chloroform: n-hexane: 30:70 (volume ratio)) to obtain the target compound. Elemental analysis Structure (molecular formula C)86H56N2): theoretical value C92.44; h5.05; n2.51; test values are: c92.41; h5.07; and (3) N2.50. MS (M/z) (M +): theoretical value is 1116.44, found 1116.37.
1H NMR (400MHz, chloroform-d) delta 7.84(dd,6H), 7.66-7.53 (m,4H), 7.52-7.32 (m,17H), 7.32-7.21 (m,12H), 7.21-7.11 (m,6H), 7.08-6.97 (m,8H),6.83–6.70(m,3H)。
The following compounds (all starting materials used are provided by Mitsuoku) were prepared in the same manner as in examples 1 and 2, and the synthetic starting materials are shown in Table 1 below, and the nuclear magnetic data are shown in tables 1 to 1 below. The electron barrier material used in the invention is synthesized according to the patents TWI600637B and CN101508670A, and the used raw materials are all provided by the energy conservation in China.
TABLE 1
TABLE 1-1
Detection method
Glass transition temperature Tg: measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter, Nachi company, Germany), the rate of temperature rise was 10 ℃/min.
HOMO energy level: the test was conducted by an ionization energy test system (IPS3) and was conducted in an atmospheric environment.
Eg energy level: based on the ultraviolet spectrophotometry (UV absorption) baseline of the material single film and the ascending side of the first absorption peak, a tangent is taken, and the numerical value of the intersection point of the tangent and the baseline is calculated.
Hole mobility: the material was fabricated into a single charge device and measured by space charge (induced) limited current method (SCLC).
Triplet energy level T1: the material was dissolved in toluene solution and tested by Hitachi F4600 fluorescence spectrometer.
The results of the physical property tests are shown in Table 2.
TABLE 2
As can be seen from the data in table 2 above, the compound of the present invention has a suitable HOMO level, a higher hole mobility, and a wider band gap (Eg), and can realize an organic electroluminescent device having high efficiency, low voltage, and long lifetime.
Preparation of organic electroluminescent device
The molecular structural formula of the materials involved in the following preparation is as follows:
device comparative example 1
The organic electroluminescent device was prepared as follows:
a) using transparent glass as a substrate, washing an anode layer (ITO (15nm)/Ag (150nm)/ITO (15nm)) on the substrate, respectively ultrasonically cleaning the anode layer for 15 minutes by using deionized water, acetone and ethanol, and then treating the anode layer for 2 minutes in a plasma cleaner;
b) on the anode layer washed, a hole transport material HT1 and a P-type dopant material HI1 were placed in two evaporation sources under a vacuum of 1.0E-5The vapor deposition rate of a compound HT1 under Pa pressure is controlled to be
Controlling the evaporation rate of the P-type doping material HI1 to be
Are combined togetherPerforming mixed evaporation to form a hole injection layer with the thickness of 10 nm;
c) evaporating a hole transport layer on the hole injection layer in a vacuum evaporation mode, wherein the hole transport layer is made of a compound HT1 and has the thickness of 120 nm;
d) evaporating an electron blocking layer EB-1 on the hole transmission layer in a vacuum evaporation mode, wherein the thickness of the electron blocking layer EB-1 is 10 nm;
e) evaporating a luminescent layer material on the electron blocking layer in a vacuum evaporation mode, wherein a host material is BH1, a guest material is BD1, the mass ratio is 97:3, and the thickness is 20 nm;
f) evaporating ET1 and LiQ on the light-emitting layer in a vacuum evaporation mode, wherein the mass ratio of ET1 to LiQ is 50:50, the thickness is 30nm, and the layer serves as an electron transport layer;
g) evaporating LiF on the electron transport layer in a vacuum evaporation mode, wherein the thickness of the LiF is 1nm, and the LiF is an electron injection layer;
h) vacuum evaporating an Mg: Ag (1:1) electrode layer with the thickness of 16nm on the electron injection layer, wherein the layer is a cathode layer;
i) CPL material CPL-1 is evaporated in vacuum on the cathode layer, and the thickness is 70 nm.
Device comparative examples 2 to 5
The procedure of comparative device example 1 was followed except that the organic materials in steps b) and c) were respectively replaced with organic materials as shown in table 3.
Device comparative example 6
The procedure of comparative device example 1 was followed except that the doping ratio of the p-type dopant material in step b) was adjusted to 1%.
Device comparative examples 7 to 10
The procedure of comparative device example 6 was followed except that the organic materials in steps b) and c) were respectively replaced with organic materials as shown in Table 3.
Device comparative examples 11 to 15
The procedure of comparative device example 1 was followed except that the organic materials in steps b), c) and f) were respectively replaced with organic materials as shown in table 3.
Device production examples 1 to 23
The procedure of comparative device example 1 was followed except that the organic materials in steps b) and c) were respectively replaced with organic materials as shown in table 3.
Device production examples 24 to 46
The procedure of comparative device example 6 was followed except that the organic materials in steps b) and c) were respectively replaced with organic materials as shown in Table 3.
Device production examples 47 to 69
The procedure of comparative device example 1 was followed except that the organic materials in b), c) and f) were respectively replaced with organic materials as shown in table 3.
TABLE 3
After the OLED light-emitting device was prepared as described above, the cathode and the anode were connected by a known driving circuit, and various properties of the device were measured. The device measurement performance results of examples 1 to 69 and comparative examples 1 to 15 are shown in table 4.
TABLE 4
Note: LT95 refers to the time it takes for the device luminance to decay to 95% of the original luminance at a luminance of 1200 nits;
voltage, current efficiency and color coordinates were tested using the IVL (current-voltage-brightness) test system (frastd scientific instruments, su);
the life test system is an EAS-62C type OLED life test system of Japan scientific research Co.
The high-temperature service life refers to the time for the brightness of the device to decay to 80% of the original brightness under the condition of 80 ℃ and the brightness of 1000 nits;
as can be seen from table 4, the results of comparative examples 1 to 5, device examples 1 to 23, the amine compound of the present invention, which is used as a hole transport material, effectively reduces the device voltage and improves the device lifetime due to its higher carrier transport rate.
As can be seen from the results of comparative examples 6 to 10 and device examples 24 to 46 in table 4, the amine compound of the present invention, which is used as a hole transport material, has a lower driving voltage even at a lower doping ratio of a P-type dopant material due to a higher carrier transport rate, and can effectively mitigate the risk of Cross-talk caused by a higher P-doping ratio.
The amine compound can effectively improve the glass transition temperature of the material because the introduced fluorenyl is a large conjugated rigid group, and has excellent evaporation stability because the groups have excellent film phase stability and evaporation stability, so that the interface stability of the device under a high-temperature condition is effectively improved, and the device has excellent high-temperature service life.
In addition, as can be seen from the results of comparative examples 11 to 15 and examples 47 to 69, the amine-based compound of the present invention is effectively improved in device efficiency by being used in combination with a specific electron transport layer material.
While the invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the described embodiments. But, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The foregoing embodiments are therefore to be considered in all respects illustrative and not restrictive.
Description of the symbols
30: organic light emitting diode
1: anode
9: covering layer
8: cathode electrode
7: electron injection layer
6: electron transport layer
5: light emitting area
3: hole transport layer
4: electron blocking layer
2: hole injection layer
10: hole transport region
20: electron transport region
Claims (10)
1. An amine compound represented by the general formula (1):
wherein
n, m each independently represent a number 0,1 or 2, and m + n is 2 or 3;
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b independently represents phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenyl or terphenyl;
p and q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group;
ar represents one of the following groups;
o, c, a, b each independently represent the number 1 or 2;
R6to R9Each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a naphthyl group, a biphenylyl group or an adamantyl group;
L、L1each independently represents phenylene, naphthylene or biphenylene,
L2represents a single bond, phenylene, naphthylene or biphenylene.
2. The amine compound of the general formula (1) according to claim 1, wherein
m + n is 2, and Ar represents formula (2), formula (4), or formula (5);
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b independently represents phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenyl or terphenyl;
p, q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group;
o, a, b represent the numbers 1 or 2;
L1represented by phenylene, naphthylene or biphenylene,
L2represents a single bond, phenylene, naphthylene or biphenylene;
R6、R8to R9Expressed as a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a naphthyl group, a biphenylyl group or an adamantyl group.
3. The amine compound of the general formula (1) according to claim 1, wherein
m represents a number 1 or 2, and m + n is 2,
ar is represented by formula (3);
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b independently represents phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenyl or terphenyl;
p, q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group;
R7represented by a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a naphthyl group, a biphenylyl group or an adamantyl group;
l represents phenylene, naphthylene or biphenylene.
4. The amine compound of the general formula (1) according to claim 1, wherein
m + n is 3, and Ar represents formula (6);
the dotted line indicates that the two groups are not connected or are connected by a single bond;
A. b independently represents phenyl or naphthyl;
with the proviso that when the dotted line indicates no attachment, B represents naphthyl;
R、R1represented by phenyl, naphthyl, biphenyl or terphenyl;
p, q each independently represent a number 1,2 or 3;
R2、R3、R4、R5each independently represents a hydrogen atom, a protium atom, a deuterium atom, a tritium atom, a phenyl group, a tert-butyl group or an adamantyl group.
5. The amine compound of general formula (1) according to claim 1, characterized in that said amine compound of general formula (1) is selected from any one of the following compounds:
6. an organic electroluminescent device comprising an anode, a hole transporting region, a light emitting region, an electron transporting region and a cathode in this order from bottom to top, wherein the hole transporting region comprises the amine compound of the general formula (1) according to any one of claims 1 to 5.
7. The organic electroluminescent device according to claim 6, wherein the hole transport region comprises a hole injection layer, a hole transport layer and an electron blocking layer in this order from bottom to top, and the hole injection layer and the hole transport layer comprise the amine compound of formula (1) according to any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 6 or 7, wherein the electron transport region comprises a nitrogen heterocyclic compound represented by the following general formula (7):
wherein
Ar1、Ar2And Ar3Independently of one another, represents substituted or unsubstituted C6-C30Aryl, substituted or unsubstituted C containing one or more hetero atoms5-C30Heterocyclyl, said heteroatoms being independently from each other selected from N, O or S;
l represents substituted or unsubstituted C6-C30Arylene radical, substituted or unsubstituted C containing one or more hetero atoms5-C30(ii) heterocyclylene, each of said heteroatoms being independently selected from N, O or S;
n represents 1 or 2;
X1、X2、X3independently of one another, N or CH, with the proviso that X1、X2、X3At least one group in (a) represents N.
9. Use of the amine compounds of the general formula (1) according to any one of claims 1 to 5 as hole transport materials in organic electroluminescent devices.
10. A display device comprising the organic electroluminescent device according to any one of claims 6 to 8.
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