CN115677557A - Aromatic amine compound and organic electroluminescent device comprising same - Google Patents
Aromatic amine compound and organic electroluminescent device comprising same Download PDFInfo
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- CN115677557A CN115677557A CN202111224376.7A CN202111224376A CN115677557A CN 115677557 A CN115677557 A CN 115677557A CN 202111224376 A CN202111224376 A CN 202111224376A CN 115677557 A CN115677557 A CN 115677557A
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- -1 Aromatic amine compound Chemical class 0.000 title claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 11
- 238000002347 injection Methods 0.000 claims description 51
- 239000007924 injection Substances 0.000 claims description 51
- 125000001624 naphthyl group Chemical group 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 230000005525 hole transport Effects 0.000 claims description 31
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 26
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000004305 biphenyl Chemical group 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000004431 deuterium atom Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 6
- 125000004957 naphthylene group Chemical group 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 93
- 230000000903 blocking effect Effects 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 7
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 166
- 239000000758 substrate Substances 0.000 description 21
- 239000010408 film Substances 0.000 description 16
- 239000011368 organic material Substances 0.000 description 15
- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 239000004020 conductor Substances 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 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
- 230000008569 process Effects 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 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 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 229940125904 compound 1 Drugs 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 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
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005070 sampling 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
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 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
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-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
- 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
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- 229910014265 BrCl Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 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
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 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
- 150000004056 anthraquinones Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 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
- 229940126214 compound 3 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 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
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 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
- 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
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 239000007788 liquid Substances 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 239000012299 nitrogen atmosphere Substances 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
- 239000012074 organic phase Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 230000000704 physical effect Effects 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
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000004059 quinone derivatives 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
- 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
- 230000000630 rising effect Effects 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
- 239000004065 semiconductor Substances 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
- 238000004528 spin coating Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000005406 washing 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
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses an aromatic amine compound and an organic electroluminescent device comprising the same, wherein the aromatic amine compoundThe structure of the compound is shown as a general formula (1):
the compound has excellent hole transmission capability and exciton blocking capability, and can simultaneously show the effects of improving the efficiency of a device and prolonging the service life when a light-emitting layer auxiliary layer material of an organic electroluminescent device is formed by using the aromatic amine compound, particularly the efficiency of the device is improved.
Description
Technical Field
The invention relates to the technical field of semiconductor materials, in particular to an aromatic amine compound and an organic electroluminescent device comprising the same.
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 mismatch between the hole injection and transport rate and the electron injection and transport rate results in large deviation of a recombination region, which is not beneficial to the stability 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 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. The blue light host material used in the current market is mostly a partial electron main body, due to the preferential injection of holes under low current density, the pressure on the hole transmission side is relieved to a certain extent, along with the increase of current density, the quantity of injected electrons can be more and more, the composite region is caused to shift to the hole side, the pressure on the hole side is larger and larger, in order to prevent the transfer of excitons to the hole side, the light-emitting auxiliary layer material is required to effectively block the excitons, and the holes can be efficiently transmitted to the light-emitting layer. At present, the materials of the light-emitting auxiliary layer are mostly traditional arylamine structures, a branched chain is selected from a carbazole group or a dibenzofuran group, the anti-exciton stability of the structures can not meet the requirement, the hole mobility under high current density still needs to be improved, the carrier balance of the light-emitting layer can be ensured, and the phenomenon that due to insufficient holes, a composite region shifts to one side of hole transmission, the efficiency of a device is reduced, and the service life is shortened is prevented.
Disclosure of Invention
In view of the above problems in the prior art, the present applicant provides an aromatic amine compound, where the organic compound of the present invention has excellent hole transport capability (especially hole mobility at high current density) and exciton blocking capability, and when a light-emitting auxiliary layer material of an organic electroluminescent device is formed by using the aromatic amine compound of the present invention, the effects of improving device efficiency and prolonging device lifetime can be simultaneously exhibited, and especially, the improvement of device efficiency is very significant.
The technical scheme of the invention is as follows: an aromatic amine compound, the structure of which is shown as the general formula (1):
in the general formula (1), ar 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl 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;
m and n represent 1,2 or 3;
the R is 1 Expressed as phenyl, naphthyl, dibenzofuranyl, benzofuranyl or furanyl;
said R is 2 Represented by a structure represented by general formula (2) or general formula (3), and the general formula (2) and the general formula (3) are represented by* The site is connected with a and b, b and c or c and d sites of the general formula (1) in a loop;
l is shown 1 、L 2 Each independently represents a direct bond, phenylene, naphthylene, or biphenylene;
in the general formula (3), X represents an oxygen atom or N (R);
the R represents phenyl, naphthyl or biphenyl;
the substituent of the substituted or unsubstituted group is selected from one or more of deuterium atom, methyl, ethyl, tertiary butyl, phenyl, naphthyl, biphenyl, benzofuryl, dibenzofuryl and furyl.
The invention also provides an organic electroluminescent device which sequentially comprises an anode, a hole transport region, a luminescent region, an electron transport region and a cathode, wherein the hole transport region comprises the aromatic amine compound.
The beneficial technical effects of the invention are as follows:
(1) According to the aromatic amine compound, the carbazole polycyclic group and the amino group are in a meta position, the ortho position of the carbazole polycyclic group is provided with a specific substituent group, the carbazole group adopts a polycyclic mode to increase the stability of the carbazole group, the ortho position is provided with the substituent group to enable the conformation of carbazole to be more stable, and the amino group is further connected with the specific substituent group, so that the compound disclosed by the invention has more excellent exciton blocking capability, excitons are enabled to be better localized in a light-emitting region, the exciton concentration of the light-emitting region is ensured to be higher, and the light-emitting efficiency is further improved.
Compared with CN110577511A, the compound of the invention is distinguished by performing ring merging modification on a carbazole group, and compared with CN110317184A, the compound of the invention is distinguished by improving a connecting group on an amino group, and the improvement enables the compound of the invention to have more excellent exciton blocking capability and hole mobility under high current density, and the compound of the invention is applied to a device, improves the efficiency of the device and has excellent service life of the device.
(2) The connection mode and the specific group of the compound ensure that the energy levels with differential carrier conduction are formed in the molecular structure of the arylamine, so that different carrier conduction channels are formed, and the compound is favorable for carrier injection and conduction among different energy level material combinations, and further favorable for obtaining the interface stability between the compound and the adjacent layer material, thereby being favorable for obtaining the good driving life of an application device.
(3) And because the compound has a stable structure, under the condition that hole injection becomes strong under high current density, holes can still be conducted to the luminescent layer through different carrier conduction channels, so that the hole concentration under high current density is ensured, and the luminous efficiency of the device is improved.
(4) Because the structural characteristics of the organic compound of the present invention are favorable for increasing the glass transition temperature of molecules and simultaneously reducing the vapor deposition temperature of molecules, that is, even if the molecular weight of the structure is relatively high, the vapor deposition temperature can be ensured to be relatively low, and the excellent performance is not only favorable for thermal vapor deposition of materials and controlling the thermal decomposition rate of the materials, thereby improving the stability of the materials in device application.
Moreover, for the arylamine molecular structural formula with the characteristics of the invention, besides the connection mode of the arylamine group and the bridging group, the ligand connected to the arylamine is optimized, which is beneficial to further improving the performance of the material. The phenyl group, the naphthyl group, the dibenzofuran group, the phenanthrene group and other groups are selected, so that the stability and the mobility of the material can be improved, the accurate regulation and control of the HOMO energy level of the material can be facilitated, and the good device application effect of the material can be further obtained.
The organic functional materials forming the OLED device not only comprise hole injection conducting materials, but also comprise electron injection conducting materials and light emitting layer materials, so that the OLED device has a good application effect, and needs a good carrier balance degree for protection, therefore, in order to obtain the best application effect of the device, the aromatic amine compound matched with the characteristic structure provided by the invention also needs specific electron type materials for matching. Based on the intensive research of the present inventors, the electronic-type material is preferably a material containing structural characteristics of azabenzene, such as a triazine-based material, a pyridine-based material, a pyrazine-based material, or the like, or a compound containing these characteristic groups. The aromatic amine compound is combined with the nitrogen heterocyclic ring electron transport material, so that electrons and holes are easy to obtain the optimal balance state, and the aromatic amine compound has higher efficiency and excellent service life.
Drawings
Fig. 1 is a cross-sectional view of an organic electroluminescent device according to the present invention.
In the drawings, 1 denotes a substrate layer; 2 represents an anode layer; 3 represents a hole injection layer; 4 represents a hole transport layer; 5 denotes a light emission auxiliary layer; 6 represents a light-emitting layer; 7 represents a hole blocking layer; 8 denotes an electron transport layer; 9 denotes an electron injection layer; 10 is denoted as cathode layer; and 11 denotes a cover layer.
FIG. 2 is the nuclear magnetic hydrogen spectrum of Compound 3;
FIG. 3 shows the nuclear magnetic hydrogen spectrum of compound 17.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. The following description of at least one exemplary embodiment is merely illustrative in nature and is in no way intended to limit the invention, its application, or uses. All other embodiments, which can be obtained by a person skilled in the art without inventive step based on the embodiments of the present invention, are within the scope of protection of the present 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 example embodiments according to the present application. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
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. 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 numbers 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 away 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 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 a conductive characteristic according to the Highest Occupied Molecular Orbital (HOMO) level.
In this specification, the electron characteristics refer to characteristics that are capable of accepting 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.
A compound represented by the general formula (1)
In the general formula (1), ar 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl 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;
m and n represent 1,2 or 3;
the R is 1 Represented by phenyl, naphthyl, dibenzofuranyl, benzofuranyl or furanyl;
the R is 2 The structure is represented by a general formula (2) or a general formula (3), and the general formula (2) and the general formula (3) are connected with a site a and b, a site b and c or a site c and a site d of the general formula (1) in a ring-merging mode through a site x;
l is shown as 1 、L 2 Each independently represents a direct bond, phenylene, naphthylene, or biphenylene;
in the general formula (3), X represents an oxygen atom or N (R);
the R represents phenyl, naphthyl or biphenyl;
the substituent of the substituted or unsubstituted group is selected from one or more of deuterium atom, methyl, ethyl, tertiary butyl, phenyl, naphthyl, biphenyl, benzofuryl, dibenzofuryl and furyl.
In a preferred embodiment, the structure of the compound is represented by general formula (1-1) to general formula (1-9):
in the general formulae (1-1) to (1-9), ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl 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;
m and n represent 1,2 or 3;
the R is 1 Represented by phenyl, naphthyl, dibenzofuranyl, benzofuranyl or furanyl;
said R is 2 The structure is represented by a general formula (2) or a general formula (3), and the general formula (2) and the general formula (3) are connected with a site a and b, a site b and c or a site c and a site d of the general formula (1) in a ring-merging mode through a site x;
l is shown as 1 、L 2 Each independently represents a direct bond, phenylene, naphthylene, or biphenylene;
in the general formula (3), X represents an oxygen atom or N (R);
the R represents phenyl, naphthyl or biphenyl;
the substituent of the substituted or unsubstituted group is selected from one or more of deuterium atom, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, benzofuranyl and dibenzofuranyl.
Preferably, the structure of the compound is shown as a general formula (4):
in the general formula (4), ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl 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;
the R is 1 Expressed as phenyl, naphthyl, dibenzofuranyl, benzofuranyl or furanyl;
the R is 2 The structure is represented by a general formula (2) or a general formula (3), and the general formula (2) and the general formula (3) are connected with a site a and b, a site b and c or a site c and a site d of the general formula (1) in a ring-merging mode through a site x;
l is shown 1 、L 2 Each independently represents a direct bond, phenylene, naphthylene, or biphenylene;
in the general formula (3), X represents an oxygen atom or N (R);
the R represents phenyl, naphthyl or biphenyl;
the substituent of the substituted or unsubstituted group is selected from one or more of deuterium atom, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, benzofuranyl, dibenzofuranyl and furanyl.
In a preferred embodiment, the R group 1 Represented by phenyl; the R is 2 Represented by a structure represented by the general formula (2); ar is 1 、Ar 2 At least one of them is selected from dibenzofuranyl groups.
In a preferred embodiment, the R 1 Represented by naphthyl; the R is 2 Represented by a structure represented by the general formula (2); ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted naphthyl groupSubstituted biphenylyl, substituted or unsubstituted terphenylyl, substituted or unsubstituted dibenzofuranyl.
In a preferred embodiment, the R group 1 Represented by phenyl or naphthyl; the R is 2 Represented by a structure represented by the general formula (3); ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, or a substituted or unsubstituted terphenylyl group.
In a preferred embodiment, the R group 1 Is represented by a dibenzofuranyl group; the R is 2 Is represented by a structure shown in a general formula (3) or a general formula (2); ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, or a substituted or unsubstituted terphenylyl group.
In a preferred embodiment, the R group 1 Expressed as furyl; the R is 2 Represented by a structure represented by general formula (3); ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, or a substituted or unsubstituted terphenylyl group.
Preferably, the specific structure of the compound is any one of the following structures:
organic electroluminescent device
The present invention provides an organic electroluminescent device using an arylamine 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 including an arylamine-based compound of formula (1), a light emitting region, an electron transport region, and a cathode.
Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light-emitting layer auxiliary layer, and the light-emitting layer auxiliary layer includes the aromatic amine compound of general formula (1).
Preferably, the electron transport region comprises a nitrogen heterocyclic compound represented by the general formula (4):
wherein Ar is 5 、Ar 6 、Ar 7 Independently of one another, from substituted or unsubstituted C 6 -C 30 Aryl radicalSubstituted or unsubstituted C containing one or more hetero atoms 5 -C 30 One of heterocyclic groups;
L 3 is a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C containing one or more hetero atoms 5 -C 30 One of a heterocyclylene group;
X 1 、X 2 、X 3 independently of one another, N or CH, X 1 、X 2 、X 3 Represents N;
each of said heteroatoms is independently selected from N, O or S;
the substituent for substituting the "substituted or unsubstituted" group is one or more of a deuterium atom, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridyl group, or a pyrimidyl group.
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 having a high work function to aid hole injection, and may be, for example, a metal such as nickel, platinum, copper, zinc, silver, or an alloy 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 and is typically 50-500nm, preferably 70-300nm, and more preferably 100-200nm, with the combination of ITO and Ag being preferred for use in the present invention for metals and metal oxides.
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 or alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, aluminum, silver, tin, and combinations thereof; materials of multilayer structure, such as LiF/Al, li 2 O/Al and BaF 2 and/Ca, but is not limited thereto. The thickness of the cathode depends on the material used and is generally from 10 to 50nm, preferably from 15 to 20nm.
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). As the host material, a compound containing an anthracene group 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 present invention, one or two host material compounds are included 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 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 the fluorescent or phosphorescent characteristics of the organic electroluminescent device. Specific examples of the phosphorescent guest material include metal complexes of iridium, platinum and the like, and 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-10:
in the light emitting region of the present invention, the ratio of the host material to the guest material used is 99.
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 provided between the anode and the light emitting region, and includes a hole injection layer, a hole transport layer, and a light emission auxiliary 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. In a preferred embodiment of the present invention, the hole injection layer is a mixed film layer of a host organic material and a P-type dopant material. In order to smoothly inject holes from the anode into the organic film layer, the HOMO level of the host organic material must have a certain characteristic as the P-type dopant material, and thus it is expected that a charge transfer state between the host material and the dopant material is generated, ohmic contact between the hole injection layer and the anode is realized, and efficient injection of holes from the electrode into 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 doping material is less than or equal to 0.4eV. Therefore, for hole-type host materials with different HOMO levels, different P-type doping materials need to be selected to match with the hole-type 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, organic materials of arylamine, hexanitrile hexaazatriphenylene, organic materials of quinacridone, organic materials of perylene, 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 doping 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 not limited thereto.
In a preferred embodiment of the present invention, the P-type doping material used is selected from any one of the following compounds P-1 to P-8:
in one embodiment of the present invention, the ratio of host organic material to P-type dopant material used is 99.
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 dopant material, and the arylamine compound is an arylamine compound of the 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, 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. Specific examples thereof include: aromatic amine-based organic materials, conductive polymers, block copolymers having both conjugated portions and non-conjugated portions, and the like, but are not limited thereto. In a preferred embodiment, the hole transport layer contains the same aromatic amine-based organic compound 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.
Luminescence auxiliary layer
In the organic electroluminescent device of the present invention, the light-emitting auxiliary layer may be disposed between the hole transport layer and the light-emitting layer, and particularly, contacts the light-emitting layer. The light-emission auxiliary layer is provided to contact the light-emitting layer, and therefore, hole transfer at the interface of the light-emitting layer and the hole transport layer can be precisely controlled. In one embodiment of the present invention, the material of the luminescence auxiliary layer is selected from aromatic amine compounds described by general formula (1). The thickness of the luminescence auxiliary 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, the 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. 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 used 3 Metal 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 No.: 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 LG 201), oxadiazole derivatives, and the like.
In a preferred organic electroluminescent device of the present invention, the electron transport layer comprises a nitrogen heterocyclic compound of the general formula (4):
wherein Ar is 5 、Ar 6 、Ar 7 Independently of one another, represents substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C containing one or more hetero atoms 5 -C 30 One of heterocyclic groups;
L 3 is a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C containing one or more hetero atoms 5 -C 30 One of a heterocyclylene group;
X 1 、X 2 、X 3 independently of one another, N or CH, X 1 、X 2 、X 3 At least one group of (a) represents N;
each of said heteroatoms is independently selected from N, O or S;
the substituent used for the substituent group is one or more of deuterium atom, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, pyridyl and pyrimidyl.
Preferred embodiment, said Ar 5 、Ar 6 、Ar 7 Independently of each other, represents 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 pyrimidyl, substituted or unsubstituted dibenzothiophene and substituted or unsubstituted quinolyl;
said L is 3 Represents a single bond, phenylene, biphenylene or naphthylene;
the substituent used for the substituent group is one or two of deuterium atom, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl, pyridyl and pyrimidyl
In a preferred embodiment of the present invention, the electron transport layer comprises any one of the compounds selected from the group consisting of:
in a more preferred embodiment of the present invention, the electron transport layer comprises any one of the compounds selected from the group consisting of:
in a preferred embodiment of the present invention, the electron transport layer comprises, in addition to the compound of formula (4), other compounds conventionally used in electron transport layers, such as Alq3, liQ, preferably LiQ. In a more preferred embodiment of the present invention, the electron transport layer is composed of one of the compounds of the general formula (4) and one of the other compounds conventionally used for electron transport layers (preferably LiQ).
The hole injection and transport rates of the hole transport region containing the arylamine compound of the present invention can be well matched to the electron injection and transport rates. Preferably, the hole injection and transport rate of the hole transport region containing the arylamine 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).
Therefore, in a particular embodiment of the present invention, relatively better technical results are achieved using electron transport regions comprising or consisting of one or more nitrogen heterocyclic derivatives of the general formula (4) in combination with hole transport regions comprising the arylamine compounds of the present invention.
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 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 in thickness.
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.
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 electroluminescent device according to an embodiment of the present invention.
Referring to fig. 1, the organic electroluminescent device according to an embodiment of the present invention includes an anode 2 and a cathode 10 facing 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, which are sequentially disposed between the anode 2 and the cathode 10, and a capping layer 11 disposed on a substrate 1 and the cathode under the anode 2.
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, the respective layers are preferably 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.
Preparation examples
Example 1: synthesis of Compound 1
0.06mol of the raw material B-1 was charged into a 500ml three-necked flask in a nitrogen atmosphere, and a mixed solvent (300 ml of toluene, 90ml of H) was added 2 O) dissolving the raw materials, introducing nitrogen, stirring for 1 hour, and then slowly adding 0.05mol of the raw materials A-1 and 0.1mol of K 2 CO 3 、0.005molPd(PPh 3 ) 4 The reaction was heated to 90 ℃ for 8 hours, and the reaction was observed by Thin Layer Chromatography (TLC) until the reaction was complete. And 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 is obtained. The resulting material was purified by silica gel column to give intermediate P-1 with purity 99.37% and yield 89.2%. Elemental analysis Structure (molecular formula C) 12 H 8 BrCl): theoretical value: c,53.87; h,3.01; br,29.87; cl,13.25; test values are: c,53.80; h,3.03; br,29.89; cl,13.28.LC-MS: measurement value: 266.87 ([ M + H)] + ) (ii) a Accurate quality: 265.95.
adding 0.01mol of intermediate P-1,0.012mol of raw material C-1 and 150ml of toluene into a three-mouth bottle under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10 -5 molPd 2 (dba) 3 ，5×10 -5 Heating the mol of tri-tert-butylphosphine and 0.03mol of sodium tert-butoxide to 105 ℃, performing reflux reaction for 20 hours, and sampling a sample point plate to show that no raw material C-1 remains and the reaction is complete; naturally cooling to room temperature, filtering, rotatably steaming the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain an intermediate M-1 with the purity of 99.14% and the yield of 83.12%. Elemental analysis Structure (molecular formula C) 28 H 18 ClN): theoretical values are as follows: c,83.26; h,4.49; n,3.47; cl,8.78; test values are: c,83.20; h,4.51; n,3.50; cl,8.80.LC-MS: measurement value: 404.25 ([ M + H)] + ) (ii) a Accurate quality: 403.11.
adding 0.01mol of raw material D-1,0.012mol of intermediate M-1 and 150ml of toluene into a three-neck flask under the protection of nitrogen, stirring and mixing, and then adding 5 multiplied by 10 -5 molPd 2 (dba) 3 ，5×10 -5 Heating the mol of tri-tert-butylphosphine and 0.03mol of sodium tert-butoxide to 105 ℃, performing reflux reaction for 24 hours, and sampling a sample point plate to show that no intermediate M-1 remains and the reaction is complete; naturally cooling to room temperature, filtering, rotatably evaporating the filtrate until no fraction is obtained, and passing through a neutral silica gel column to obtain the target compound with the purity of 98.91 percent and the yield of 79.91 percent. Elemental analysis Structure (molecular formula C) 52 H 36 N 2 ): theoretical value: c,90.67; h,5.27; n,4.07; test values: c,90.74; h,5.23; and N,4.05.LC-MS: measurement value: 689.37 ([ M + H ]] + ) (ii) a Accurate quality: 688.29.
the following compounds were prepared in the same manner as in example 1, and the synthetic raw materials are shown in table 1 below;
TABLE 1
Detection method
Glass transition temperature Tg: measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter, nachi Germany), the rate of temperature rise was 10 ℃/min.
HOMO energy level: the test was conducted by an ionization energy test system (IPS 3) and the test was conducted in a vacuum environment.
Eg energy level: the measurement was carried out by means of a two-beam ultraviolet-visible spectrophotometer (model: TU-1901) using a tangent line based on the ultraviolet spectrophotometric (UV absorption) baseline of the material single film and the rising side of the first absorption peak, and calculating the value of the intersection of the tangent line and the baseline.
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 tested by Fluorolog-3 series fluorescence spectrometer from Horiba under 2X 10 -5 A toluene solution of mol/L.
The results of the specific 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 and a long lifetime.
Preparation of organic electroluminescent device
The molecular structural formula of the materials involved in the following preparation is as follows:
comparative device example 1
The organic electroluminescent device was prepared as follows:
as shown in fig. 1, the anode layer 2 (Ag (100 nm)) is washed, i.e., washed with alkali, washed with pure water, dried, and then washed with ultraviolet rays and ozone, to remove organic residues on the surface of the anode layer, in the substrate layer 1. On the anode layer 2 after the above washing, HT1 and P-1 were deposited by a vacuum deposition apparatus in a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 to P-1 was 97. Next, HT-1 was evaporated to a thickness of 117nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 10nm as a luminescence auxiliary layer 5. After the evaporation of the material of the light-emitting auxiliary layer is finished, the light-emitting layer 6 of the OLED light-emitting device is manufactured, and the structure of the light-emitting layer 6 comprises that BH-1 used by the OLED light-emitting layer 6 is used as a main material, BD-1 is used as a doping material, the doping proportion of the doping material is 3% by weight, and the thickness of the light-emitting layer is 20nm. After the light-emitting layer 6, HB1 was deposited by evaporation to a film thickness of 8nm to form a hole-blocking layer 7. On the hole-blocking layer 7, ET-1 and Liq were continuously deposited by vacuum deposition at a mass ratio of ET-1 to Liq of 1, and the vacuum deposition film thickness of this material was 30nm, which layer was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. An Mg/Ag electrode layer having a thickness of 16nm was formed on the electron injection layer 9 by a vacuum deposition apparatus, the mass ratio of Mg to Ag was 1. CP-1 was vacuum-deposited on the cathode layer 10 at 70nm to form a capping layer 11.
Comparative examples 2 to 5 of devices
The process of comparative example 1 of the device was followed except that the organic materials in the hole injection layer and the hole transport layer were respectively replaced with organic materials as shown in table 3.
Device examples 1-23
The process of comparative example 1 of the device was followed except that the organic materials in the hole injection layer, the hole transport layer, or the electron transport layer were respectively replaced with organic materials as shown in table 3.
TABLE 3
In the above table, taking the example 1 row as an example, "P-1": 9710nm denotes the thickness of the layer; "110nm" in the table of the fourth column indicates that the material used is compound 1, the layer being 10nm thick. And so on in other tables.
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 results of measuring the properties of the devices of examples 1 to 23 and comparative examples 1 to 5 are shown in Table 4.
TABLE 4
Note: LT95 means a luminance of 50mA/cm 2 In this case, the time taken for the luminance of the device to decay to 95% of the original luminance;
voltage, current efficiency and color coordinates were tested using the IVL (current-voltage-brightness) test system (forskold scientific instruments, su zhou); the current density is 10mA/cm 2 ；
The life test system is an EAS-62C type OLED life test system of Japan scientific research Co.
As can be seen from the results of comparative examples 1 to 5 and device examples 1 to 23 in table 4, when the aromatic amine compound of the present invention is used as a light-emitting auxiliary layer material, the efficiency and lifetime of the device are effectively improved due to the higher carrier transport rate and exciton blocking capability, and especially the efficiency of the device is unexpectedly and significantly improved (on the premise of maintaining a certain lifetime advantage).
Claims (10)
1. An aromatic amine compound, characterized in that the structure of the compound is shown as a general formula (1):
in the general formula (1), ar 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl 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;
m and n represent 1,2 or 3;
the R is 1 Expressed as phenyl, naphthyl, dibenzofuranyl, benzofuranyl or furanyl;
the R is 2 The structure is represented by a general formula (2) or a general formula (3), and the general formula (2) and the general formula (3) are connected with a site a and b, a site b and c or a site c and a site d of the general formula (1) in a ring-merging mode through a site x;
l is shown as 1 、L 2 Each independently represents a direct bond, phenylene, naphthylene, or biphenylene;
in the general formula (3), X represents an oxygen atom or N (R);
the R represents phenyl, naphthyl or biphenyl;
the substituent of the substituted or unsubstituted group is selected from one or more of deuterium atom, methyl, ethyl, tert-butyl, phenyl, naphthyl, biphenyl, benzofuranyl, furanyl and dibenzofuranyl.
2. The aromatic amine compound of claim 1, wherein the structure of the compound is represented by general formula (1-1) to general formula (1-9):
in general formula (1-1) to general formula (1-9), ar 1 、Ar 2 、m、n、R 1 、L 1 、L 2 And X has the same definition as in claim 1.
3. The aromatic amine compound of claim 1, wherein R is 1 Represented by phenyl; the R is 2 Represented by a structure represented by general formula (2); ar is 1 、Ar 2 At least one of them is selected from dibenzofuranyl groups.
4. The aromatic amine compound of claim 1, wherein R is 1 Represented as naphthyl; said R is 2 Represented by a structure represented by general formula (2); ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenylyl group, or a substituted or unsubstituted dibenzofuranyl group.
5. The aromatic amine compound of claim 1, wherein R is 1 Represented by phenyl or naphthyl; the R is 2 Represented by a structure represented by the general formula (3); ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, or a substituted or unsubstituted terphenylyl group.
6. The aromatic amine compound of claim 1, wherein R is 1 Is represented by dibenzofuranyl; the R is 2 Is represented by a structure shown in a general formula (3) or a general formula (2); ar is 1 、Ar 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, or a substituted or unsubstituted terphenylyl group.
7. The aromatic amine compound of claim 1, wherein the specific structure of the compound is any one of the following structures:
8. an organic electroluminescent device comprising an anode, a hole transport region, a light-emitting region, an electron transport region and a cathode in this order, wherein the hole transport region comprises the aromatic amine-based compound according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the hole transport region comprises a hole injection layer, a hole transport layer, and a light-emitting layer auxiliary layer comprising the aromatic amine-based compound according to any one of claims 1 to 7.
10. The organic electroluminescent device according to claim 8, wherein the electron transport region comprises a nitrogen heterocyclic compound represented by general formula (4):
wherein Ar is 5 、Ar 6 、Ar 7 Independently of one another, from substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C containing one or more hetero atoms 5 -C 30 One of heterocyclic groups;
L 3 is a single bond, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C containing one or more hetero atoms 5 -C 30 One of a heterocyclylene group;
X 1 、X 2 、X 3 independently of one another, N or CH, X 1 、X 2 、X 3 Represents N;
each of said heteroatoms is independently selected from N, O or S;
the substituent used for substituting the "substituted or unsubstituted" group is one or more of a deuterium atom, a phenyl group, a naphthyl group, a biphenyl group, a dibenzofuranyl group, a dibenzothienyl group, a pyridyl group, or a pyrimidyl group.
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| CN116670253A (en) * | 2021-07-21 | 2023-08-29 | 株式会社Lg化学 | Organic light emitting device |
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| CN110317184A (en) * | 2018-03-29 | 2019-10-11 | 江苏三月光电科技有限公司 | A kind of compound based on double dimethyl fluorenes, preparation method and applications |
| CN110577511A (en) * | 2018-06-07 | 2019-12-17 | 江苏三月光电科技有限公司 | Compound with triarylamine structure as core and preparation method thereof |
| CN113135928A (en) * | 2020-01-17 | 2021-07-20 | 江苏三月光电科技有限公司 | Organic compound and organic electroluminescent device comprising same |
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