CN116217409A - Aromatic amine compound and organic electroluminescent device prepared from same - Google Patents
Aromatic amine compound and organic electroluminescent device prepared from same Download PDFInfo
- Publication number
- CN116217409A CN116217409A CN202310103867.9A CN202310103867A CN116217409A CN 116217409 A CN116217409 A CN 116217409A CN 202310103867 A CN202310103867 A CN 202310103867A CN 116217409 A CN116217409 A CN 116217409A
- Authority
- CN
- China
- Prior art keywords
- represented
- phenyl
- biphenylene
- phenylene
- naphthyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 Aromatic amine compound Chemical class 0.000 title claims abstract description 86
- 230000005525 hole transport Effects 0.000 claims abstract description 26
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 70
- 238000002347 injection Methods 0.000 claims description 49
- 239000007924 injection Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 39
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 235000010290 biphenyl Nutrition 0.000 claims description 35
- 239000004305 biphenyl Substances 0.000 claims description 35
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 32
- 125000001624 naphthyl group Chemical group 0.000 claims description 32
- 125000001544 thienyl group Chemical group 0.000 claims description 31
- 125000002541 furyl group Chemical group 0.000 claims description 30
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 17
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 16
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
- JYAKNSNAABYQBU-UHFFFAOYSA-N 2h-dibenzofuran-1-one Chemical compound O1C2=CC=CC=C2C2=C1C=CCC2=O JYAKNSNAABYQBU-UHFFFAOYSA-N 0.000 claims 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 90
- 230000000903 blocking effect Effects 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 6
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 238000001356 surgical procedure Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 166
- 239000002994 raw material Substances 0.000 description 31
- 239000000758 substrate Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000010408 film Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 239000011368 organic material Substances 0.000 description 15
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000010025 steaming Methods 0.000 description 7
- 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 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000005070 sampling Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical group 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910044991 metal oxide Inorganic materials 0.000 description 4
- 150000004706 metal oxides Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 239000002131 composite material Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 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
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 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
- 229940125782 compound 2 Drugs 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 125000004431 deuterium atom Chemical group 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 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
- 229920001721 polyimide Polymers 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 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
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 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
- 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 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
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-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
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 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
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001562 benzopyrans Chemical class 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- 229920001400 block copolymer Polymers 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
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000000605 extraction 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
- 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
- 238000010030 laminating Methods 0.000 description 1
- 238000007648 laser printing Methods 0.000 description 1
- 239000002346 layers by function 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
- 238000004519 manufacturing process Methods 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
- 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
- VQSRKMNBWMHJKY-YTEVENLXSA-N n-[3-[(4ar,7as)-2-amino-6-(5-fluoropyrimidin-2-yl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-7a-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]23[C@@H](CN(C2)C=2N=CC(F)=CN=2)CSC(N)=N3)=C1 VQSRKMNBWMHJKY-YTEVENLXSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 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
- 229960005222 phenazone Drugs 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination 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
- 238000004528 spin coating Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 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
- 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
- 238000004017 vitrification Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The invention discloses an aromatic amine compound and an organic electroluminescent device prepared from the aromatic amine compound, belonging to the technical field of semiconductor materialsThe field of surgery. The structure of the aromatic amine compound is shown as a general formula (1):
the organic compound has excellent hole transport capability (especially hole mobility under high current density) and exciton blocking capability, and can simultaneously show the effects of improving the efficiency of the device and prolonging the service life, especially the device efficiency is remarkably improved when the aromatic amine compound is used for forming the light-emitting auxiliary layer material of the organic electroluminescent device.
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 prepared from the aromatic amine compound.
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 offset of a composite region is large, and the stability of the device is not facilitated, so that how to adjust the balance degree of holes and electrons and adjust the composite region is 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. The blue light host materials currently used in the market are mostly electron-biased host materials, the pressure on the hole transport side is relieved to a certain extent due to the preferential injection of holes at low current density, the amount of electron injection is increased along with the increase of the current density, the recombination region is shifted to the hole side, the pressure on the hole side is increased, and in order to prevent the excitons from being transferred to the hole side, the light-emitting auxiliary layer material is required to be capable of effectively blocking the excitons and efficiently transporting the holes to the light-emitting layer. At present, most of materials of a light-emitting auxiliary layer are of a traditional aromatic amine structure, carbazole groups or dibenzofuran groups are selected by branched chains, the stability of excitons of the structure still cannot meet the requirements, hole mobility under high current density still needs to be improved, so that the carrier balance of the light-emitting layer can be ensured, and the phenomenon that a composite region deviates to one side of hole transmission due to insufficient holes, so that the efficiency of a device is reduced and the service life of the device is shortened is prevented.
Disclosure of Invention
In view of the above problems in the prior art, the present invention provides an aromatic amine compound and an organic electroluminescent device prepared therefrom, which have excellent hole transporting ability (especially hole mobility at high current density) and exciton blocking ability, and which can simultaneously exhibit effects of improving device efficiency and prolonging lifetime, especially remarkably improving device efficiency, when used to form a light-emitting auxiliary layer material of an organic electroluminescent device.
The technical scheme of the invention is as follows:
an aromatic amine compound, the structure of which is shown in a general formula (1):
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl;
the R is 2 Represented by phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenylOne of the substituted naphthyl groups;
the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
Preferably, in formula (1), when R 2 Represented by dibenzofuranyl, L 1 Represented by phenylene, said R 1 Not denoted biphenyl;
when R is 2 Represented by dibenzofuranyl, L 1 Represented by biphenylene, said R 1 Not denoted phenyl.
Preferably, the structure of the aromatic amine compound is shown as a general formula (1-1):
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl;
the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
Preferably, the structure of the aromatic amine compound is shown as a general formula (1-2);
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl;
the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
Preferably, the structure of the aromatic amine compound is shown as a general formula (1-3);
wherein the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
Preferably, the structure of the aromatic amine compound is shown as a general formula (1-4):
wherein the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl; the L is 2 Represented by phenylene or biphenylene.
Preferably, the structure of the aromatic amine compound is shown as a general formula (1-5);
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl; the L is 1 Represented by a single bond, phenylene or biphenylene.
Preferably, the structure of the aromatic amine compound is shown as a general formula (1-6) or a general formula (1-7);
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl;
the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl;
the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
Preferably, the structure of the compound is shown as a general formula (1-8):
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl;
the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl;
the L is 2 Represented by phenylene or biphenylene.
Preferably, the structure of the compound is shown as a general formula (1-9):
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl;
the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl;
the L is 2 Represented by a single bond, phenylene or biphenylene.
Preferably, the structure of the compound is shown as a general formula (1-10):
wherein the R is 1 Represented by phenyl, biphenyl, furyl, thiaOne of a phenoyl group and a benzothienyl group;
the R is 2 Represented by one of phenyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl;
the L is 2 Represented by a single bond, phenylene or biphenylene.
Preferably, the structure of the aromatic amine compound is shown as a general formula (1-11):
wherein the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl;
the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
Preferably, the structure of the aromatic amine compound is shown as a general formula (1-12);
wherein the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl; the L is 2 Represented by phenylene or biphenylene.
Preferably, the L 1 Selected from the following groups:
a single bond,
Any one of them;
the L is 2 Selected from the following groups:
any one of them.
Preferably, the R 2 Selected from the following groups:
Preferably, the R 1 Selected from the following groups:
Further preferably, the specific structure of the aromatic amine 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 compound.
The functional layer of the organic electroluminescent device is positioned on a substrate, and the substrate can be adjacent to the anode or the cathode.
An organic electroluminescent device comprises a substrate, an anode, a hole transport region, a light emitting region, an electron transport region and a cathode, wherein the hole transport region comprises the aromatic amine compound.
An organic electroluminescent device comprises an anode, a hole transport region, a light emitting region, an electron transport region, a cathode and a substrate in sequence, wherein the hole transport region comprises the aromatic amine compound.
Preferably, the hole transport region includes a hole injection layer, a hole transport layer, and a light emitting layer auxiliary layer including the aromatic amine compound.
Further preferably, the electron transport region comprises an aza-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, substituted or unsubstituted C containing one or more hetero atoms 3 -C 30 One of the heterocyclic groups;
L 3 represented by single bonds, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C containing one or more hetero atoms 3 -C 30 One of the heterocyclylene groups; x is X 1 、X 2 、X 3 Independently of one another, N or CH, X 1 、X 2 、X 3 Wherein at least one of them represents N;
the heteroatom is 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 or pyrimidinyl.
A lighting or display element comprising said organic light emitting device.
The beneficial technical effects of the invention are as follows:
(1) The special collocation connection mode between the aromatic amine compound groups enables the compound to have more excellent exciton blocking capability, enables excitons to be better localized in a light-emitting area, ensures higher exciton concentration in the light-emitting area, and further improves light-emitting efficiency.
The compound has more excellent exciton blocking capability and hole mobility under high current density, and has excellent device service life when being applied to devices, and the efficiency of the devices is improved.
(2) The connection mode and the specific groups of the compound ensure that different carrier conduction energy levels are formed in the molecular structure of the aromatic amine, so that different carrier conduction channels are formed, carrier injection and conduction between matching of materials with different energy levels are facilitated, interface stability between the compound and adjacent layer materials is facilitated, and good driving life of an application device is facilitated.
(3) The compound has stable structure, and can still conduct holes to the light-emitting layer through different carrier conduction channels under the condition that hole injection becomes strong under high current density, so that the hole concentration under the high current density is ensured, and the light-emitting efficiency of the device is further improved.
(4) The structural characteristics of the compound disclosed by the invention are beneficial to improving the vitrification transfer temperature of molecules, and simultaneously beneficial to reducing the evaporation temperature of the molecules, namely, even though the molecular weight of the structure is relatively high, the compound can ensure that the compound has relatively low evaporation temperature, and the excellent performance is beneficial to thermal evaporation of materials and control of the thermal decomposition rate of the materials, so that the stability of the materials in device application is improved.
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 aromatic amine compound matched with the characteristic structure disclosed by the invention is required to be matched for obtaining 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 compound containing these characteristic groups. The aromatic amine compound is combined with the aza-benzene ring electron transport material, so that electrons and holes are easy to obtain an 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 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 a light emitting layer auxiliary 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.
FIG. 2 is a nuclear magnetic resonance spectrum of compound 4;
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of compound 22;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of compound 29.
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 example embodiments in accordance with 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, 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.
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; multiple onesLayer structure materials, such as LiF/Al, li 2 O/Al and BaF 2 /Ca, but is 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 a light emitting layer 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 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 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.
Auxiliary layer of luminous layer
In the organic electroluminescent device of the present invention, the light emitting layer auxiliary layer may be disposed between the hole transport layer and the light emitting layer, and particularly contact the light emitting layer. The light emitting layer auxiliary layer is disposed to contact the light emitting layer, and thus, hole transfer at the interface of the light emitting layer and the hole transport layer can be precisely controlled. In one embodiment of the present invention, the light emitting layer auxiliary layer material is selected from the aromatic amine compound of the general formula (1). The thickness of the auxiliary layer of the light emitting 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. As the electron transport layer of the organic electroluminescent device of the present invention, those known in the art for organic electronics can be usedElectron transport layer materials of light-emitting devices, e.g. in Alq 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), and 2- (4- (9, 10-bis (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 an aza-heterocyclic compound of 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, substituted or unsubstituted C containing one or more hetero atoms 3 -C 30 One of the heterocyclic groups;
L 3 represented by single bonds, substituted or unsubstituted C 6 -C 30 Arylene, substituted or unsubstituted C containing one or more hetero atoms 3 -C 30 One of the heterocyclylene groups; x is X 1 、X 2 、X 3 Independently of one another, N or CH, X 1 、X 2 、X 3 Wherein at least one of them represents N;
the heteroatom is 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 or pyrimidinyl.
Preferably, the Ar 5 、Ar 6 、Ar 7 Independently of each other, are represented by a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstitutedOne of dibenzothiophene, substituted or unsubstituted quinolinyl;
the L is 3 Represented by a single bond, phenylene, biphenylene, or naphthylene.
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-transporting layer comprises, in addition to the nitrogen heterocyclic compound of the general formula (4), other compounds conventionally used for electron-transporting 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 compound 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.
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, a light emitting layer auxiliary 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.
Preparation example
Example 1: synthesis of Compound 2
In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material B-1,0.012mol of raw material A-1 and 150ml of toluene are added and mixed under stirring, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 20 hours, and sampling a dot plate to show that no raw material B-1 remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction exists, and passing through a neutral silica gel column to obtain the compound 2. Elemental analysis structure (molecular formula C) 50 H 35 N): theoretical value: c,92.42; h,5.43; n,2.16; test value: c,92.38; h,5.45; n,2.18.LC-MS: measurement value: 650.37 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 649.28.
example 2: synthesis of raw material B-4
In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material C-1,0.012mol of raw material D-1 and 150ml of toluene are added and mixed under stirring, and then 5X is added10 -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 10 hours, and sampling a dot plate to show that no raw material C-1 remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain raw material B-4. Elemental analysis structure (molecular formula C) 36 H 25 NO): theoretical value: c,88.68; h,5.17; n,2.87; test value: c,88.69; h,5.15; n,2.84.LC-MS: measurement value: 488.33 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 487.19.
example 3: synthesis of raw material B-5
In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material C-2,0.012mol of raw material D-2 and 150ml of toluene are added and stirred and mixed, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 12 hours, and sampling a dot plate to show that no raw material C-2 remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain raw material B-5. Elemental analysis structure (molecular formula C) 34 H 25 N): theoretical value: c,91.24; h,5.63; n,3.13; test value: c,91.28; h,5.61; n,3.10.LC-MS: measurement value: 448.35 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 447.20.
example 4: synthesis of raw material B-13
In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material C-3,0.012mol of raw material D-3 and 150ml of toluene were added and mixed under stirring, and then 5X 10 was added -5 mol Pd 2 (dba) 3 ，5×10 -5 mol of tri-tert-butyl phosphorus, 0.03mol of sodium tert-butoxide, heating to 105 ℃, refluxing for 13 hours, samplingThe dot plate shows that no raw material C-3 remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain raw material B-13. Elemental analysis structure (molecular formula C) 36 H 25 NO): theoretical value: c,88.68; h,5.17; n,2.87; test value: c,88.74; h,5.14; n,2.88.LC-MS: measurement value: 488.24 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 487.19.
example 5: synthesis of raw material B-14
In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material C-4,0.012mol of raw material D-4 and 150ml of toluene were added and mixed under stirring, and then 5X 10 was added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, and carrying out reflux reaction for 10.5 hours, wherein a sampling point plate shows that no raw material C-4 remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain raw material B-14. Elemental analysis structure (molecular formula C) 36 H 27 N): theoretical value: c,91.30; h,5.75; n,2.96; test value: c,91.24; h,5.79; n,2.98.LC-MS: measurement value: 474.15 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 473.21.
example 6: synthesis of raw material B-15
Adding 0.01mol of C-5,0.012mol of D-5 and 150ml of toluene under nitrogen protection into a three-necked flask, stirring and mixing, and adding 5×10 -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 14 hours, and sampling a dot plate to show that no raw material C-5 remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain raw material B-15. Element(s)Analysis Structure (molecular formula C) 36 H 27 N): theoretical value: c,91.30; h,5.75; n,2.96; test value: c,91.27; h,5.77; n,2.90.LC-MS: measurement value: 474.32 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 473.21.
example 7: synthesis of raw material B-16
In a three-necked flask, under the protection of nitrogen, 0.01mol of raw material C-6,0.012mol of raw material D-2 and 150ml of toluene are added and stirred and mixed, and then 5X 10 is added -5 mol Pd 2 (dba) 3 ，5×10 -5 Heating 0.03mol of tri-tert-butyl phosphorus and 0.03mol of sodium tert-butoxide to 105 ℃, carrying out reflux reaction for 17 hours, and sampling a dot plate to show that no raw material C-6 remains and the reaction is complete; naturally cooling to room temperature, filtering, steaming the filtrate until no fraction is present, and passing through neutral silica gel column to obtain raw material B-16. Elemental analysis structure (molecular formula C) 34 H 25 N): theoretical value: c,91.24; h,5.63; n,3.13; test value: c,91.27; h,5.66; n,3.15.LC-MS: measurement value: 448.34 ([ M+H)] + ) The method comprises the steps of carrying out a first treatment on the surface of the Accurate quality: 447.20.
the following compounds were prepared in the same manner as in example 1, and the synthetic materials are shown in the following table 1;
TABLE 1
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 transparent glass, and the anode layer 2 (Ag (100 nm)) is washed, that is, sequentially alkali-washed, pure water-washed, dried, and then ultraviolet-ozone-washed 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 auxiliary layer 5 for the light-emitting layer. After the evaporation of the auxiliary material for the light-emitting layer is completed, the light-emitting layer 6 of the OLED light-emitting device is manufactured, and the structure of the auxiliary material for 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 proportion of the doping material is 3% by weight, and the film thickness of the light-emitting layer is 20nm. After the light-emitting layer 6 was deposited, HB-1 was further deposited to a thickness of 8nm as a hole blocking layer 7. And (3) 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 deposition 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, 65nm of CP-1 was vacuum-deposited as CPL layer 11.
Device comparative examples 2 to 10
The procedure of device comparative example 1 was conducted except that the organic materials in the auxiliary layer of the light-emitting layer were replaced with the organic materials shown in table 2, respectively.
Device examples 1 to 16
The procedure of device comparative example 1 was conducted except that the organic materials in the auxiliary layer of the light-emitting layer were replaced with the organic materials shown in table 2, respectively.
TABLE 2
Taking example 1 as an example in the table above, the "P-1:ht-1=3:9710 nm" in the second column table indicates that the hole injection layer is made of compound HT-1 and P-type dopant material P-1,3:97 indicates that the weight ratio of P-type dopant material P-1 to compound HT-1 is 3:97, and 10nm indicates the thickness of the layer; the fourth column of the table "210nm" indicates that the material used is compound 2 and the layer thickness is 10nm. 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 16 and comparative examples 1 to 10 are shown in Table 3.
TABLE 3 Table 3
Note that: LT95 means that the brightness is 50mA/cm 2 In the case, the time taken for the brightness of the device to decay to 95% of the original brightness;
the current efficiency and color coordinates are measured using an IVL (Current-Voltage-luminance) test systemSoviet scientific instruments limited); the current density was 10mA/cm 2 ；
The life test system is an EAS-62C OLED life test system of japan systems research limited.
From the results of comparative examples 1 to 10 in table 3, device examples 1 to 16 show that the use of the aromatic amine compound of the present invention as a light-emitting auxiliary layer material effectively improves the device efficiency and lifetime due to the higher carrier transport rate and exciton blocking capability, and especially the device efficiency is unexpectedly improved significantly (while maintaining certain lifetime advantages).
Claims (12)
1. An aromatic amine compound is characterized in that the structure of the compound is shown as a general formula (1):
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl;
the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl;
the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
2. The aromatic amine compound according to claim 1, wherein the structure of the compound is represented by the general formula (1-1):
wherein the R is 1 Represented by phenyl, naphthyl, biphenyl, and furolOne of a pyranyl, thienyl, benzothienyl;
the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
3. The aromatic amine compound according to claim 1, wherein the structure of the compound is represented by the general formula (1-2);
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl;
the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
4. The aromatic amine compound according to claim 1, wherein the structure of the compound is represented by the general formula (1-3);
wherein the L is 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene.
5. The aromatic amine compound according to claim 1, wherein the structure of the compound is represented by the general formula (1-4):
wherein the R is 2 Represented by phenyl, naphthyl, biphenyl, benzofuranyl, furanylOne of thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl; the L is 2 Represented by phenylene or biphenylene.
6. The aromatic amine compound according to claim 1, wherein the structure of the compound is represented by general formula (1-5);
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl; the L is 1 Represented by a single bond, phenylene or biphenylene.
7. The aromatic amine compound according to claim 1, wherein the structure of the compound is represented by general formula (1-6):
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl,
the L is 1 Represented by a single bond, phenylene or biphenylene, said L 2 Represented by phenylene or biphenylene;
alternatively, the structure of the compound is shown as a general formula (1-7):
wherein the R is 2 Represented by phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthylIs one of the L 2 Represented by phenylene or biphenylene;
alternatively, the structure of the compound is shown as a general formula (1-8):
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl, said R 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl, said L 2 Represented by phenylene or biphenylene;
alternatively, the structure of the compound is shown as a general formula (1-9):
wherein the R is 1 Represented by one of phenyl, naphthyl, biphenyl, furyl, thienyl, benzothienyl, said R 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl, said L 2 Represented by a single bond, phenylene or biphenylene;
alternatively, the structure of the compound is shown as a general formula (1-10):
wherein the R is 1 Represented by one of phenyl, biphenyl, furyl, thienyl, benzothienyl, R 2 Represented by phenyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranOne of a pyranyl group, a dibenzothiophenyl group, a phenyl-substituted naphthyl group, the L 2 Represented by a single bond, phenylene or biphenylene;
alternatively, the structure of the compound is shown as a general formula (1-11):
wherein the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl, said L 1 Represented by a single bond, phenylene or biphenylene; the L is 2 Represented by phenylene or biphenylene;
or the structure of the aromatic amine compound is shown as a general formula (1-12);
wherein the R is 2 Represented by one of phenyl, naphthyl, biphenyl, benzofuranyl, furanyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, phenyl-substituted naphthyl; the L is 2 Represented by phenylene or biphenylene.
8. The aromatic amine compound according to claim 1, wherein,
the L is 1 Selected from the following groups:
a single bond,
Any one of them;
the L is 2 Selected from the group consisting of：
the R is 2 Selected from the following groups:
the R is 1 Selected from the following groups:
9. The aromatic amine compound according to claim 1, wherein the specific structure of the compound is any one of the following structures:
10. 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 compound according to any one of claims 1 to 9.
11. The organic electroluminescent device according to claim 10, 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 compound according to any one of claims 1 to 9.
12. A lighting or display element, characterized in that it comprises the organic light emitting device according to any one of claims 10-11.
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| CN110078705A (en) * | 2018-01-26 | 2019-08-02 | 三星显示有限公司 | Organic electroluminescence device and monoamine compound for organic electroluminescence device |
| WO2021206477A1 (en) * | 2020-04-10 | 2021-10-14 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using same, and electronic device thereof |
| CN113519073A (en) * | 2019-11-11 | 2021-10-19 | 株式会社Lg化学 | Organic light emitting device |
| CN113861041A (en) * | 2020-06-30 | 2021-12-31 | 北京鼎材科技有限公司 | Compound and application thereof |
| WO2022039106A1 (en) * | 2020-08-17 | 2022-02-24 | 保土谷化学工業株式会社 | Organic electroluminescent element |
| CN114175296A (en) * | 2019-11-05 | 2022-03-11 | 株式会社Lg化学 | Organic light emitting device |
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| CN110078705A (en) * | 2018-01-26 | 2019-08-02 | 三星显示有限公司 | Organic electroluminescence device and monoamine compound for organic electroluminescence device |
| CN114175296A (en) * | 2019-11-05 | 2022-03-11 | 株式会社Lg化学 | Organic light emitting device |
| CN113519073A (en) * | 2019-11-11 | 2021-10-19 | 株式会社Lg化学 | Organic light emitting device |
| WO2021206477A1 (en) * | 2020-04-10 | 2021-10-14 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using same, and electronic device thereof |
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