CN116023355B - Aromatic amine organic compound and organic electroluminescent device prepared from same - Google Patents
Aromatic amine organic compound and organic electroluminescent device prepared from same Download PDFInfo
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- CN116023355B CN116023355B CN202111232483.4A CN202111232483A CN116023355B CN 116023355 B CN116023355 B CN 116023355B CN 202111232483 A CN202111232483 A CN 202111232483A CN 116023355 B CN116023355 B CN 116023355B
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- -1 Aromatic amine organic compound Chemical class 0.000 title claims abstract description 46
- 239000000463 material Substances 0.000 claims abstract description 106
- 230000005525 hole transport Effects 0.000 claims abstract description 41
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 11
- 238000002347 injection Methods 0.000 claims description 60
- 239000007924 injection Substances 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000004982 aromatic amines Chemical class 0.000 claims description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000004431 deuterium atom Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
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- 239000011799 hole material Substances 0.000 description 69
- 239000000758 substrate Substances 0.000 description 22
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- 230000000903 blocking effect Effects 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000004770 highest occupied molecular orbital Methods 0.000 description 15
- 239000011368 organic material Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002994 raw material Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
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- 238000005259 measurement Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- 239000000741 silica gel Substances 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
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- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 3
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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
- 239000004642 Polyimide Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 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
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 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 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 238000002390 rotary evaporation Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000011787 zinc oxide Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-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
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound 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 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 compound 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
- XWQVQSXLXAXOPJ-QNGMFEMESA-N 4-[[[6-[5-chloro-2-[[4-[[(2r)-1-methoxypropan-2-yl]amino]cyclohexyl]amino]pyridin-4-yl]pyridin-2-yl]amino]methyl]oxane-4-carbonitrile Chemical compound C1CC(N[C@H](C)COC)CCC1NC1=CC(C=2N=C(NCC3(CCOCC3)C#N)C=CC=2)=C(Cl)C=N1 XWQVQSXLXAXOPJ-QNGMFEMESA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 238000004082 amperometric method Methods 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- 230000001174 ascending effect Effects 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
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical group N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
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- 239000012043 crude product Substances 0.000 description 1
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
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- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 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
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 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
- 229910052759 nickel Inorganic materials 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
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl 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
- 230000000704 physical effect Effects 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 150000004059 quinone derivatives Chemical class 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 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
- 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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 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
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an arylamine organic compound, which has a structure shown in a general formula (1): The organic compound has excellent hole transport capacity and thermal stability, and can simultaneously show the effects of improving the efficiency of the device and prolonging the service life of the device, in particular prolonging the high-temperature service life of the device when the aromatic amine organic compound is used for forming the hole transport material of the organic electroluminescent device.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to an arylamine organic compound and an organic electroluminescent device prepared from the same.
Background
Carriers (holes and electrons) in an organic electroluminescent device (OLED) are respectively injected into the device by two electrodes of the device under the drive of an electric field, and meet and recombine and 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, a charge transport material is required to have good carrier mobility. The injection and transmission characteristics of the hole injection layer material and the hole transmission layer material used in the existing organic electroluminescent device are relatively weak, and the hole injection and transmission rates are not matched with the electron injection and transmission rates, so that the composite area is greatly deviated, and the stability of the device is not facilitated. In addition, reasonable energy level matching of 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, so how to adjust the balance degree of holes and electrons and adjust the recombination region is always an important subject in the field.
Blue organic electroluminescent devices are always soft ribs in full-color OLED development, so that the efficiency, service life and other performances of blue light devices are not fully improved until now, and therefore, how to improve the performances of the devices is still a critical problem and challenge in the field. Since the blue light host materials currently used in the market are mostly electron-biased host materials, the hole transport materials are required to have excellent hole transport properties in order to adjust the carrier balance of the light emitting layer. The better the hole injection and transmission, the more the adjusting composite area is deviated to the side far away from the electron blocking layer, so that the light is emitted far away from the interface, the performance of the device is improved, and the service life of the device is prolonged. Therefore, the hole transport region material is required to have high hole injection property, high hole mobility, high electron blocking property, and high electron weatherability.
In the prior art, in a high-temperature environment, as the difference between electron mobility and hole mobility is more obvious, a blue light device shows rich electrons and holes and has poor service life in the high-temperature environment, and in order to improve the high-temperature service life of the blue light device, the mobility of a hole transport material, especially the mobility under the high-temperature condition, needs to be improved.
Disclosure of Invention
In view of the above problems in the prior art, the applicant provides an arylamine organic compound and an organic electroluminescent device prepared from the same. The organic compound has excellent hole transport capacity and thermal stability, and can simultaneously show the effects of improving the efficiency of the device and prolonging the service life of the device, in particular prolonging the high-temperature service life of the device when the aromatic amine organic compound is used for forming the hole transport material of the organic electroluminescent device.
The technical scheme of the invention is as follows:
An arylamine organic compound has a structure shown in a general formula (1):
In the general formula (1), each of the L 1、L2 is independently represented by one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted biphenylene group;
the A is represented by a structure shown in a general formula (2) or a structure shown in a general formula (3);
Each of said R 1-R4 is independently represented by one of a substituted or unsubstituted C 6-C30 aryl, a substituted or unsubstituted C 3-C30 heteroaryl containing one or more heteroatoms;
The substituent for the substituent group is one or more of deuterium atom, methyl, ethyl, tertiary butyl, adamantyl, phenyl, naphthyl and biphenyl.
Preferably, the structure of the compound is shown as any one of the general formulas (1-1) to (1-4):
In the general formulae (1-1) to (1-4), the meaning of R 1-R4、L1-L2 is as defined above.
Preferably, the structure of the compound is shown as any one of the general formulas (2-1) to (2-6):
The meaning of R 1-R4、L2 is as defined above.
Preferably, each R 1-R4 is independently represented as one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted furyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted piperonyl group, a substituted or unsubstituted fluorenyl group, and a substituted or unsubstituted carbazolyl group.
Further preferably, L 1、L2 is independently represented as phenylene or naphthylene.
Preferably, the structure of the compound is shown as any one of the general formulas (1-5) to (1-8):
in the general formulae (1-5) to (1-8), the meaning of R 1-R4、L1-L2 is as defined above.
Further preferably, the specific structure of the compound is any one of the following structures:
An organic electroluminescent device comprising, in order, an anode, a hole transporting region, a light emitting region, an electron transporting region, and a cathode, the hole transporting region comprising the aromatic amine-type organic compound.
Preferably, the hole transport region includes a hole injection layer, a first hole transport layer, and a second hole transport layer, and the first hole transport layer and the hole injection layer include the arylamine-type organic compound.
Preferably, the first hole transport layer comprises the arylamine organic compound, and the hole injection layer is composed of the arylamine organic compound and other doping materials conventionally used for hole injection layers.
Preferably, the electron transport region comprises an azaheterocyclic compound represented by the general formula (4):
Wherein Ar 1、Ar2、Ar3 is independently selected from one of substituted or unsubstituted C 6-C30 aryl, substituted or unsubstituted C 3-C30 heteroaryl containing one or more heteroatoms;
L 3 represents one of a single bond, a substituted or unsubstituted C 6-C30 arylene group, a substituted or unsubstituted C 3-C30 heteroarylene group containing one or more heteroatoms;
x 1、X2、X3 independently of one another represents N or CH, at least one of X 1、X2、X3 represents N;
the heteroatoms are each independently selected from N, O or S;
The substituent for the substituent group is one or more of deuterium atom, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, pyridyl and pyrimidinyl.
The beneficial technical effects of the invention are as follows:
the arylamine hole material provided by the invention takes the diarylamine as a basic skeleton, and the diarylamine takes the spiro derivative as a bridging group, and the connection mode ensures that the molecule with the characteristics of the invention has the following advantages:
(1) Because the bridging group of the aromatic amine hole conducting material is a large conjugated ring, electron clouds can be uniformly distributed on the whole molecule, and for the hole carrier conducting material, the wider the distribution of HOMO on the molecule, the higher the ratio of fragments participating in HOMO conduction on the molecule, so that the higher hole carrier conducting efficiency is easy to obtain.
(2) The aromatic amine conducting material takes the bi-aromatic amine as a basic framework, so that energy levels with differentiated carrier conduction can be formed in an aromatic amine molecular structure, and different carrier conduction channels are formed, which is beneficial to carrier injection and conduction between matching of materials with different energy levels, and further beneficial to obtaining the interface stability between the aromatic amine material and adjacent materials, and further beneficial to obtaining the good high-low temperature driving life of an application device.
(3) The compound disclosed by the invention has higher carrier forward rate, so that the compound disclosed by the invention is applied as a hole transport material, the concentration of holes injected into a main structure is increased, the generation of TTA effect is facilitated by the improvement of exciton concentration, the exciton recombination efficiency in a recombination region is further improved, and the device efficiency is improved.
(4) Because the structural characteristics of the arylamine organic compound are favorable for improving the vitrification transfer temperature of molecules and reducing the evaporation temperature of the molecules, namely, even though the molecular weight of the structure is relatively high, the structure can ensure that the structure has relatively low evaporation temperature, the excellent performance is not only favorable for thermal evaporation of materials, but also controls the thermal decomposition rate of the materials, so that the stability of the materials in device application is improved.
Furthermore, for the molecular structural formula of the aromatic amine, except for the connection mode of the aromatic amine group and the bridging group, the ligand connected to the aromatic amine is optimized, so that the performance of the material is further improved. For example, spirofluorene, diphenyl fluorene, carbazole, triphenylene, pyrene, phenanthrene and the like are selected, so that the flatness is strong, or groups or group derivatives (containing a parallel ring structure or groups of the same type with a substituted structure) with larger structure radius are selected, the stability and mobility of the material are improved, and meanwhile, the accurate regulation and control of the HOMO energy level of the material are facilitated, so that the good device application effect of the material is obtained.
The organic functional material forming the OLED device not only comprises the hole injection conductive material, but also comprises the electron injection conductive material and the luminescent layer material, so that good device application effect is achieved, and good carrier balance is required to be ensured, so that the arylamine material matched with the characteristic structure disclosed by the invention also needs to be matched with specific electronic materials in order to obtain the optimal device application effect. Based on the intensive studies of the present inventors, the electronic material is preferably a material containing structural characteristics of an azabenzene, such as a triazine-based material, a pyridine-based material, a pyrazine-based material, or the like, or a derivative containing these characteristic groups. The arylamine organic compound disclosed by the invention is combined with the aza-benzene ring electron transport material, so that electrons and holes are easy to obtain an optimal balance state, the arylamine organic compound has higher efficiency and excellent service life, and particularly good high-temperature service life effect of a device is easy to obtain.
Drawings
Fig. 1 is a cross-sectional view of an organic electroluminescent device according to the present invention.
In the figure, 1 represents a substrate layer; 2 represents an anode layer; 3 represents a hole injection layer; 4 represents a hole transport layer; 5 represents an electron blocking layer; 6 represents a light emitting layer; 7 represents a hole blocking layer; 8 represents an electron transport layer; 9 denotes an electron injection layer; 10 is denoted as cathode layer; 11 denotes a cover layer.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and completely with reference to the accompanying drawings, in which it is apparent that the embodiments described are only some embodiments of the present invention, but not all embodiments. The following description of at least one exemplary embodiment is merely exemplary in nature and is in no way intended to limit the invention, its application, or uses. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the present application. As used herein, the singular is also intended to include the plural unless the context clearly indicates otherwise, and furthermore, it is to be understood that the terms "comprises" and/or "comprising" when used in this specification are taken to specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof.
In the present invention, HOMO means the highest occupied orbital of a molecule, and LUMO means the lowest unoccupied orbital of a molecule unless otherwise specified. Furthermore, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between energy levels is also a comparison of the magnitudes of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level, the lower the energy of the energy level.
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. Further, 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 numbers refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, as well as other structures, words of "upper", "lower", "top" and "bottom", etc., which are used to indicate orientations, indicate only orientations in a certain specific state, and do not mean that the relevant structure can only exist in the orientations; conversely, if the structure can be repositioned, for example inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of an electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side that is farther from the substrate is the "top" side.
In this specification, the term "substituted" means that one or more hydrogen atoms on a given atom or group is replaced by the specified group, provided that the normal valence of the given atom is not exceeded in the present case.
In this specification, the hole feature refers to a feature that can supply electrons when an electric field is applied and is attributed to a conductive feature according to the Highest Occupied Molecular Orbital (HOMO) level, and holes formed in the anode are easily injected into and transported in the light emitting layer.
In this specification, the electron feature refers to a feature that can accept electrons when an electric field is applied and is attributed to a conductive feature according to the Lowest Unoccupied Molecular Orbital (LUMO) level, electrons formed in the cathode are easily injected into and transported in the light emitting layer.
In the present specification, substituted or unsubstituted C 6-C30 aryl and/or substituted or unsubstituted C 3-C30 heteroaryl means substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fused tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-biphenylyl, substituted or unsubstituted m-biphenylyl, substituted or unsubstitutedA group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted indene group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl 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 pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted naphthyridine group, an oxazinyl group, a substituted or unsubstituted benzodiazine group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzooxazinyl group, a substituted or unsubstituted benzofuranyl group, but is not limited thereto.
In the present specification, fluorenyl includes dimethylfluorenyl, diphenylfluorenyl, or spirofluorenyl.
Organic electroluminescent device
The invention provides an organic electroluminescent device using aromatic amine compounds 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 of the present invention may be a bottom-emission organic electroluminescent device, a top-emission organic electroluminescent device, and a stacked organic electroluminescent device, and is not particularly limited.
In the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices may also be used. Examples thereof are transparent substrates such as glass or transparent plastic substrates; an opaque substrate such as a silicon substrate; a flexible Polyimide (PI) film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, and water repellency. The use direction of the substrate is different according to the property 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 opposite to each other. The anode may be made of a conductor having a higher work function to aid hole injection, and may be, for example, a metal such as nickel, platinum, copper, zinc, silver, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and metal oxides, such as ZnO with Al or ITO with Ag; conductive polymers such as poly (3-methylthiophene), poly (3, 4- (ethylene-1, 2-dioxy) thiophene), and polyaniline, but are not limited thereto. The thickness of the anode depends on the material used, typically 50-500nm, preferably 70-300nm, and more preferably 100-200nm, and in the present invention, a combination of metal and metal oxide, ITO and Ag, is preferably used.
Cathode electrode
The cathode may be made of a conductor having a lower work function to aid electron injection, and may be, for example, a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, aluminum, silver, tin, and combinations thereof; multilayered structural materials such as LiF/Al, li 2 O/Al, and BaF 2/Ca, but are not limited thereto. The thickness of the cathode is generally 10-50nm, preferably 15-20nm, depending on the material used.
Light emitting region
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, a light-emitting layer material for an organic electroluminescent device 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). As host material, compounds containing anthracene groups can be used. 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 invention, one or two host material compounds are contained in the light-emitting region.
In a preferred embodiment of the invention, two host material compounds are included in the light emitting region, and the two host material compounds form an exciplex.
In a preferred embodiment of the invention, the host material of the light-emitting region used is selected from one or more of the following compounds BH-1-BH-11:
In the present invention, the light emitting region may include a phosphorescent or fluorescent guest material to improve fluorescence or phosphorescence characteristics of the organic electroluminescent device. Specific examples of the phosphorescent guest material include metal complexes of iridium, platinum, and the like, and as 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-10:
in the light-emitting region of the present invention, the ratio of host material to guest material used is 99:1 to 70:30, preferably 99:1 to 85:15 and more preferably 97:3 to 87:13 on a mass basis.
The thickness of the light emitting region 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 disposed 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 capable of sufficiently accepting 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. In a preferred embodiment of the present invention, the hole injection layer is a mixed film of host organic material and P-type dopant material. In order to enable holes to be smoothly injected into the organic film layer from the anode, the HOMO energy level of the main organic material and the P-type doping material must have certain characteristics, so that the occurrence of a charge transfer state between the main material and the doping material is expected to be realized, ohmic contact between the hole injection layer and the anode is realized, and efficient injection of holes from the electrode to the hole injection layer is realized. This feature is summarized as: the difference between the HOMO energy level of the host material and the LUMO energy level of the P-type doped material is less than or equal to 0.4eV. Therefore, for hole host materials with different HOMO energy levels, different P-type doping materials are required to be selected to be matched with the hole host materials, so that ohmic contact of an interface can be realized, and the hole injection effect is improved.
Preferably, specific examples of the host organic material include: metalloporphyrin, oligothiophene, arylamine organic materials, hexanitrile hexaazabenzophenanthrene, quinacridone organic materials, perylene organic materials, anthraquinone, polyaniline and polythiophene conductive polymers; but is not limited thereto. Preferably, the host organic material is an arylamine-based organic material.
Preferably, the P-type dopant material is a compound having charge conductivity selected from the group consisting of: quinone derivatives or metal oxides such as tungsten oxide and molybdenum oxide, but are not limited thereto.
In a preferred embodiment of the invention, the P-type doping material used is selected from any of the following compounds P-1 to P-8:
in one embodiment of the invention, the ratio of host organic material to P-type dopant material used is 99:1 to 95:5, preferably 99:1 to 97:3, on a mass basis.
In a preferred embodiment of the present invention, the hole injection layer is a mixed film layer of an arylamine compound and a P-type doping material, and the arylamine compound is an arylamine compound of general formula (1).
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, a hole transport layer may be disposed over 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. Specific examples thereof include: arylamine organic materials, conductive polymers, block copolymers having both conjugated and unconjugated portions, and the like, but are not limited thereto. In a preferred embodiment, the hole transport layer comprises the same arylamine organic compound represented by general formula (1) as the hole injection layer.
The thickness of the hole transport layer of the present invention may be 80, 100 or 200nm, preferably 100 to 150nm, but the thickness is not limited to this range.
Electron blocking layer
In the organic electroluminescent device of the present invention, an electron blocking layer may be disposed between the hole transport layer and the light emitting layer, and particularly contact the light emitting layer. The electron blocking layer is disposed to contact the light emitting layer, and thus, hole transfer at the interface of the light emitting layer and the hole transporting layer can be precisely controlled. In one embodiment of the invention, the electron blocking layer material is selected from carbazole-based aromatic amine derivatives. The thickness of the electron blocking layer 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, an electron transport region is disposed between the light emitting region and the cathode, and includes a hole blocking layer, 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. Examples of the electron transport layer material used for the organic electroluminescent device of the present invention include metal complexes of hydroxyquinoline derivatives such as Alq 3, 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. RTM.: 1459162-51-6), and imidazole derivatives such as 2- (4- (9, 10-bis (naphthalen-2-yl) anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [ d ] imidazole (CAS. RTM. 561064-11-7, commonly referred to as LG 201), and oxadiazole derivatives.
In a preferred organic electroluminescent device of the present invention, the electron transport layer comprises an aza-heterocyclic compound of the general formula (4):
Wherein Ar 1、Ar2、Ar3 is independently selected from one of substituted or unsubstituted C 6-C30 aryl, substituted or unsubstituted C 3-C30 heteroaryl containing one or more heteroatoms;
L 3 represents one of a single bond, a substituted or unsubstituted C 6-C30 arylene group, a substituted or unsubstituted C 3-C30 heterocyclylene group containing one or more heteroatoms;
X 1、X2、X3 independently of one another represents N or CH, at least one radical in X 1、X2、X3 representing N;
the heteroatoms are each independently selected from N, O or S;
The substituent for the substituent group is one or more of deuterium atom, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, pyridyl and pyrimidinyl.
Preferably, ar 1、Ar2、Ar3 is independently selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted quinolinyl;
The L 3 represents a single bond, phenylene, biphenylene, or naphthylene;
the substituent for the substituent group is one or two of deuterium atom, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, pyridyl and pyrimidinyl.
In a preferred embodiment of the present invention, the electron transport layer comprises any one of the following compounds selected from:
in a more preferred embodiment of the present invention, the electron transport layer comprises any one of the following compounds selected from:
In a preferred embodiment of the invention, the electron transport layer comprises, in addition to the compounds of the general formula (4), further compounds conventionally used for electron transport layers, for example Alq3, liQ, preferably LiQ. In a more preferred embodiment of the present invention, the electron transport layer consists of one of the compounds of formula (4) and one of the other compounds conventionally used for electron transport layers, preferably LiQ.
The hole injection and transport rate of the hole transport region containing the aromatic amine compound of the present invention can be well matched to the electron injection and transport rate. Preferably, the hole injection and transport rate of the hole transport region containing the aromatic amine compound of the present invention can be better matched with the electron injection and transport rate of the electron transport region containing the nitrogen heterocyclic derivative of the general formula (4).
Thus, in a particular embodiment of the present invention, the use of one or more electron transport regions comprising or consisting of an azaheterocyclic compound of the general formula (4) in combination with a hole transport region comprising an arylamine compound of the present invention achieves relatively better technical results.
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.
Cover layer
In order to improve the light-emitting efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer, also referred to as a capping layer) may be further added to the cathode of the device. According to the optical absorption and refraction principles, the higher the refractive index of the CPL cover layer material is, the better the CPL cover layer material is, and the smaller the light absorption coefficient is, the better the CPL cover layer material is. 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 coating typically has a thickness of 5-300nm, preferably 20-100nm and more preferably 40-80nm.
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 layer 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.
In the drawings, the thickness of layers, films, substrates, regions, etc. are exaggerated for clarity. Like numbers refer to like elements throughout. 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 electroluminescent device according to an embodiment of the present invention.
Referring to fig. 1, an organic electroluminescent device according to an embodiment of the present invention includes an anode 2 and a cathode 10 opposite to each other, a hole transport region including a hole injection layer 3, a hole transport layer 4, and an electron blocking layer 5, a light emitting layer 6, and an electron transport region including a hole blocking layer 7, an electron transport layer 8, and an electron injection layer 9, sequentially disposed between the anode 2 and the cathode 10, and a capping layer 11 disposed over a substrate 1 and the cathode under the anode 2.
The invention also relates to a method of manufacturing 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, or LITI may be used, but are not limited thereto. In the present invention, the respective layers are preferably formed by a vacuum vapor deposition method. The individual process conditions in the vacuum evaporation process can be routinely selected by those skilled in the art according to the actual needs.
The material for forming each layer according to the present invention may be used as a single layer by forming a film alone, or may be used as a single layer by forming a film after mixing with another material, or may be a laminated structure between layers formed by forming a film alone, a laminated structure between layers formed by mixing, or a laminated structure between layers formed by forming a film alone and layers formed by mixing.
The invention also relates to a full-color display device, in particular a flat panel display device, comprising the organic electroluminescent device of the invention with three pixels of red, green and blue. 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.
Example 1: synthesis of intermediate M
(1) Under nitrogen atmosphere, 0.06mol of raw material B-1 was added to a 500mL three-necked flask, a mixed solvent (300 mL of toluene, 90mL of H 2 O) was added to dissolve the raw material B-1, the mixture was stirred for 1 hour by introducing nitrogen, then 0.05mol of raw material A and 0.1mol of K 2CO3、0.005mol Pd(PPh3)4 were slowly added, the mixture was heated to 90℃and reacted for 8 hours, and the reaction was observed by Thin Layer Chromatography (TLC) until the reaction was completed. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate P-1.LC-MS: measurement value: 222.85 ([ M+H ] +); accurate quality: 221.97.
(2) In a flask, 0.06mol of intermediate P-1 and 300mL of anhydrous tetrahydrofuran are added, the mixture is cooled to-78 ℃ under the protection of nitrogen, 0.06mol of 2.5M N-butyl N-hexane solution is slowly added dropwise, the temperature is kept under stirring for 2 hours, 0.06mol of raw material C-1 is added dropwise into the solution, the reaction is carried out at room temperature for 2 hours, 1N hydrochloric acid solution is added into the reaction solution, dichloromethane is used for extraction, drying and concentration are carried out, 0.3mL of acetic acid and 0.1mL of concentrated hydrochloric acid are added into the crude product, the mixture is heated and refluxed for 5 hours, cooled and filtered, and then ethanol and tetrahydrofuran are used for recrystallization and drying to obtain intermediate M-1.LC-MS: measurement value: 510.83 ([ M+H ] +); accurate quality: 509.91.
Intermediate M was prepared in a similar manner as in example 1, as shown in table 1 below:
TABLE 1
Example 2: synthesis of Compound 310
(1) Under nitrogen atmosphere, 0.06mol of intermediate M-1 was added to a 500mL three-necked flask, a mixed solvent (300 mL of toluene, 90mL of H 2 O) was added to dissolve the intermediate, the mixture was stirred for 1 hour with nitrogen, then 0.05mol of raw material D-1 and 0.1mol of K 2CO3、0.005mol Pd(PPh3)4 were slowly added, the mixture was heated to 90℃and reacted for 8 hours, and the reaction was observed by Thin Layer Chromatography (TLC) until the reaction was completed. Naturally cooling to room temperature, adding water into the reaction system for extraction, separating liquid, and performing reduced pressure rotary evaporation on the organic phase until no fraction exists. The obtained material was purified by silica gel column to obtain intermediate N-1.LC-MS: measurement value: 628.29 ([ M+H ] +); accurate quality: 627.12.
(2) Adding 0.01mol of raw material E-1,0.012mol of intermediate N-1 and 150ml of toluene into a 250ml three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10 -5mol Pd2(dba)3,5×10-5 mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, displaying no amino compound residue, and completely reacting; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through a neutral silica gel column to obtain the target product. Elemental analysis structure (formula C 57H38N2O2): theoretical value: c,87.44; h,4.89; n,3.58; test value: c,87.49; h,4.88; n,3.57.LC-MS: measurement value: 783.31 ([ M+H ] +); accurate quality: 782.29.
The following compounds were prepared in a similar manner to example 2 and synthesized as shown in table 2 below;
TABLE 2
Example 3: synthesis of Compound 220
(1) Adding 0.01mol of raw material E-1,0.012mol of intermediate M-1 and 150ml of toluene into a 250ml three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10 -5mol Pd2(dba)3,5×10-5 mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, displaying no amino compound residue, and completely reacting; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain an intermediate O-1.LC-MS: measurement value: 552.35 ([ M+H ] +); accurate quality: 551.09.
(2) Adding 0.01mol of raw material E-3,0.012mol of intermediate O-1 and 150ml of toluene into a 250ml three-port bottle under the protection of nitrogen, stirring and mixing, then adding 5X 10 -5mol Pd2(dba)3,5×10-5 mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide, heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a dot plate, displaying no amino compound residue, and completely reacting; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through a neutral silica gel column to obtain the target product. Elemental analysis structure (formula C 51H34N2O2): theoretical value: c,86.66; h,4.85; n,3.96; test value: c,86.61; h,4.86; n,3.97.LC-MS: measurement value: 707.01 ([ M+H ] +); accurate quality: 706.26.
The following compounds were prepared in a similar manner to example 3, as shown in table 3 below;
TABLE 3 Table 3
Detection method
Glass transition temperature Tg: the temperature was increased at a rate of 10℃per minute as measured by differential scanning calorimetry (DSC, german fast Co., DSC204F1 differential scanning calorimeter).
HOMO energy level: the test was performed by an ionization energy measurement system (IPS 3) test, which was a vacuum environment.
Eg energy level: the test was performed by a double beam ultraviolet-visible spectrophotometer (model: TU-1901) based on the tangential line between the ultraviolet spectrophotometry (UV absorption) base line of the material single film and the ascending side of the first absorption peak, calculated using the value of the intersection point between the tangential line and the base line.
Hole mobility: the material was fabricated as a single charge device, measured using space charge (induced) limited amperometry (SCLC).
Triplet energy level T1: the materials were tested by a fluorescent-3 series fluorescence spectrometer from Horiba under conditions of 2X 10 -5 mol/L toluene solution.
The specific physical properties are shown in Table 4.
TABLE 4 Table 4
As can be seen from the data of table 4 above, the compounds of the present invention have suitable HOMO levels, higher hole mobility and wider band gap (Eg), and can realize organic electroluminescent devices 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 process is shown as follows:
Device comparative example 1
The organic electroluminescent device is prepared according to the following steps:
As shown in fig. 1, the substrate layer 1 is washed with an anode layer 2 (Ag (100 nm)), that is, alkali washing, pure water washing, drying, and ultraviolet-ozone washing in order to remove organic residues on the surface of the anode layer. On the anode layer 2 after the above washing, HT-1 and P-1 having film thicknesses of 10nm were vapor deposited as hole injection layers 3 by a vacuum vapor deposition apparatus, and the mass ratio of HT-1 and P-1 was 97:3. Next, HT-1 was evaporated to a thickness of 117nm as a hole transport layer 4. Subsequently EB-1 was evaporated to a thickness of 10nm as an electron blocking layer 5. After the evaporation of the electron blocking material is completed, a light emitting layer 6 of the OLED light emitting device is manufactured, and the structure of the light emitting layer comprises BH-1 used by the OLED light emitting layer 6 as a main material, BD-1 as a doping material, the doping material doping ratio is 3% by weight, and the film thickness of the light emitting layer is 20nm. After the light-emitting layer 6, the deposition of HB1 was continued, and the deposited film thickness was 8nm, thereby forming a hole blocking layer 7. And continuously evaporating ET-1 and Liq on the hole blocking layer 7, wherein the mass ratio of the ET-1 to the Liq is 1:1, the vacuum evaporation film thickness of the material is 30nm, and the layer is an electron transport layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm, which is an electron injection layer 9, was formed by a vacuum vapor deposition apparatus. On the electron injection layer 9, an Mg/Ag electrode layer having a film thickness of 16nm was prepared by a vacuum vapor deposition apparatus, and the mass ratio of Mg to Ag was 1:9, and this layer was used as the cathode layer 10. On the cathode layer 10, 70nm of CP-1 was vacuum-deposited as the coating layer 11.
Device comparative examples 2 to 6
The procedure of device comparative example 1 was conducted except that the organic materials in the hole injection layer and the hole transport layer were replaced with the organic materials shown in table 5, respectively.
Device examples 1 to 20
The procedure of device comparative example 1 was conducted except that the organic materials in the hole injection layer, the hole transport layer, or the electron transport layer were replaced with the organic materials shown in table 5, respectively.
TABLE 5
Taking example 1 row as an example in the table above, the "P-1:9=3:9710 nm" in the second column table indicates that the hole injection layer uses the compound 9 and the P-type doping material P-1, and the weight ratio of the P-type doping material to the compound 9 is 3:97, 10nm represents the thickness of the layer; the third column of the tables, "9117nm" indicates that the material used was compound 9 and the layer thickness was 117nm. And so on in other tables.
After the OLED light-emitting device was fabricated as described above, the cathode and anode were connected using a well-known driving circuit, and various properties of the device were measured.
The results of measuring the performance of the devices of examples 1 to 20 and comparative examples 1 to 6 are shown in Table 6.
TABLE 6
Note that: LT95 refers to the time taken for the device brightness to decay to 95% of the original brightness at a brightness of 1500 nits;
voltage, current efficiency and color coordinates were tested using an IVL (current-voltage-brightness) test system (fresco scientific instruments, su-state); the current density is 10mA/cm 2;
the life test system is an EAS-62C OLED life test system of japan systems research limited.
The high-temperature service life refers to the time for the brightness of the device to decay to 80 percent of the original brightness under the condition of 80 ℃ and the current density of 10mA/cm 2;
As can be seen from the results of comparative examples 1 to 6 and examples 1 to 20 of the devices in Table 6, the use of the arylamine organic compounds of the present invention as a hole injection and hole transport layer material effectively improves the efficiency and lifetime of the devices, particularly the high temperature lifetime of the devices, due to the higher carrier transport rate, and the drive voltage is also significantly reduced.
Claims (10)
1. An arylamine organic compound is characterized in that the structure of the compound is shown as a general formula (1):
In the general formula (1), L 1、L2 is respectively and independently one of single bond and phenylene;
The A is represented by a structure shown in a general formula (2) or a structure shown in a general formula (3):
r 1-R4 is independently represented as one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted bivalent phenyl, dibenzofuranyl, phenanthryl, dimethylfluorene and diphenylfluorene;
the substituent for the substituent group is one or more of deuterium atom, furyl, phenyl and naphthyl.
2. The aromatic amine-based organic compound according to claim 1, wherein the structure of the compound is represented by any one of the general formulae (1-1) to (1-4):
The meaning of R 1-R4、L1-L2 is as defined in claim 1.
3. The aromatic amine-based organic compound according to claim 1, wherein the structure of the compound is represented by any one of the general formulae (2-1) to (2-6):
the meaning of R 1-R4、L2 is as defined in claim 1.
4. The arylamine organic compound according to claim 1, wherein R 1-R4 is independently represented by one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a dibenzofuranyl group, and a phenanthryl group.
5. The aromatic amine-based organic compound according to claim 1, wherein each of the L 1、L2 is independently represented as a phenylene group.
6. An arylamine organic compound is characterized in that the specific structure of the compound is any one of the following structures:
7. An organic electroluminescent device comprising, in order, an anode, a hole transporting region, a light emitting region, an electron transporting region, and a cathode, wherein the hole transporting region comprises the aromatic amine-based organic compound according to any one of claims 1 to 6.
8. The organic electroluminescent device according to claim 7, wherein the hole transport region comprises a hole injection layer, a first hole transport layer, and a second hole transport layer, the first hole transport layer and the hole injection layer comprising the aromatic amine-type organic compound according to any one of claims 1 to 6.
9. The organic electroluminescent device according to claim 8, wherein the first hole transport layer comprises the aromatic amine-based organic compound according to any one of claims 1 to 6, and the hole injection layer is composed of the aromatic amine-based organic compound according to any one of claims 1 to 6 and other doping materials for the hole injection layer.
10. The organic electroluminescent device according to claim 7, wherein the electron transport region comprises an aza-heterocyclic compound represented by general formula (4):
Wherein Ar 1、Ar2、Ar3 is independently selected from one of substituted or unsubstituted C 6-C30 aryl, substituted or unsubstituted C 3-C30 heteroaryl containing one or more heteroatoms;
L 3 represents one of a single bond, a substituted or unsubstituted C 6-C30 arylene group, a substituted or unsubstituted C 3-C30 heteroarylene group containing one or more heteroatoms;
x 1、X2、X3 independently of one another represents N or CH, at least one of X 1、X2、X3 represents N;
the heteroatoms are each independently selected from N, O or S;
The substituent for the substituent group is one or more of deuterium atom, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, pyridyl and pyrimidinyl.
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| CN107614494A (en) * | 2015-10-06 | 2018-01-19 | 株式会社Lg化学 | Spiro-compound and the organic luminescent device for including it |
| CN107635983A (en) * | 2015-10-06 | 2018-01-26 | 株式会社Lg化学 | Spiral shell ring-based compounds and the Organic Light Emitting Diode for including it |
| WO2020036171A1 (en) * | 2018-08-17 | 2020-02-20 | 富士フイルム株式会社 | Sensor |
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Country or region after: China Address after: B312-194, No. 2 Fengwei Road, Huizhi Enterprise Center, Xishan Economic and Technological Development Zone, Xishan District, Wuxi City, Jiangsu Province, 214101 Applicant after: Jiangsu March Technology Co.,Ltd. Address before: 214112 No.210 Xinzhou Road, Wuxi City, Jiangsu Province Applicant before: Jiangsu March Technology Co.,Ltd. Country or region before: China |
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| GR01 | Patent grant | ||
| GR01 | Patent grant |