CN110590643A - 有机化合物及使用其的有机电激发光元件 - Google Patents
有机化合物及使用其的有机电激发光元件 Download PDFInfo
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- CN110590643A CN110590643A CN201811626180.9A CN201811626180A CN110590643A CN 110590643 A CN110590643 A CN 110590643A CN 201811626180 A CN201811626180 A CN 201811626180A CN 110590643 A CN110590643 A CN 110590643A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 50
- 239000000463 material Substances 0.000 claims abstract description 56
- 239000002019 doping agent Substances 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 18
- 125000005264 aryl amine group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- -1 benzofluorenyl Chemical group 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- 125000005580 triphenylene group Chemical group 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 269
- 230000015572 biosynthetic process Effects 0.000 description 136
- 238000003786 synthesis reaction Methods 0.000 description 135
- 238000000034 method Methods 0.000 description 66
- 239000010410 layer Substances 0.000 description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- UFCZRCPQBWIXTR-UHFFFAOYSA-N 2,8-dibromodibenzofuran Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3OC2=C1 UFCZRCPQBWIXTR-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 5
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 5
- DXRVYZGVVFZCFP-UHFFFAOYSA-N 2,4-dibromo-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1Br DXRVYZGVVFZCFP-UHFFFAOYSA-N 0.000 description 5
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 4
- UKGHMNPNPCSUIG-UHFFFAOYSA-N [2-(2-Naphthyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1 UKGHMNPNPCSUIG-UHFFFAOYSA-N 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- BXXLTVBTDZXPTN-UHFFFAOYSA-N methyl 2-iodobenzoate Chemical compound COC(=O)C1=CC=CC=C1I BXXLTVBTDZXPTN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- TUGMGVWOTWPOET-UHFFFAOYSA-N (2-phenylnaphthalen-1-yl)boronic acid Chemical group C1=CC2=CC=CC=C2C(B(O)O)=C1C1=CC=CC=C1 TUGMGVWOTWPOET-UHFFFAOYSA-N 0.000 description 3
- WRGKKASJBOREMB-UHFFFAOYSA-N 1,4-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Br WRGKKASJBOREMB-UHFFFAOYSA-N 0.000 description 3
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CJRHLSZJEFJDLA-UHFFFAOYSA-N methyl 5-bromo-2-iodobenzoate Chemical compound COC(=O)C1=CC(Br)=CC=C1I CJRHLSZJEFJDLA-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DFGVPVXRDYZCIA-UHFFFAOYSA-N (1-phenylnaphthalen-2-yl)boronic acid Chemical compound OB(O)C1=CC=C2C=CC=CC2=C1C1=CC=CC=C1 DFGVPVXRDYZCIA-UHFFFAOYSA-N 0.000 description 1
- AOYYQPPLTDMTIY-UHFFFAOYSA-N (2-naphthalen-1-ylphenyl)boronic acid Chemical group OB(O)C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 AOYYQPPLTDMTIY-UHFFFAOYSA-N 0.000 description 1
- HCCRIVRPKWHYOF-UHFFFAOYSA-N (3-phenylnaphthalen-2-yl)boronic acid Chemical group OB(O)C1=CC2=CC=CC=C2C=C1C1=CC=CC=C1 HCCRIVRPKWHYOF-UHFFFAOYSA-N 0.000 description 1
- UXJHQQLYKUVLIE-UHFFFAOYSA-N 1,2-dihydroacridine Chemical group C1=CC=C2N=C(C=CCC3)C3=CC2=C1 UXJHQQLYKUVLIE-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical group C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 1
- JHRMQHFRVPVGHL-UHFFFAOYSA-N 2-chloro-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(Cl)=CC=C3C=CC2=C1 JHRMQHFRVPVGHL-UHFFFAOYSA-N 0.000 description 1
- OLEBEWHIVDADAL-UHFFFAOYSA-N 2-chloro-9-phenyl-1,10-phenanthroline Chemical compound ClC1=NC2=C3N=C(C=CC3=CC=C2C=C1)C1=CC=CC=C1 OLEBEWHIVDADAL-UHFFFAOYSA-N 0.000 description 1
- WDNWGRMGIZVOEZ-UHFFFAOYSA-N 3,6-dibromo-9,9-dimethylfluorene Chemical compound BrC1=CC=C2C(C)(C)C3=CC=C(Br)C=C3C2=C1 WDNWGRMGIZVOEZ-UHFFFAOYSA-N 0.000 description 1
- WEDKTMOIKOKBSH-UHFFFAOYSA-N 4,5-dihydrothiadiazole Chemical group C1CN=NS1 WEDKTMOIKOKBSH-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- RLPAWKJLZUFLCR-UHFFFAOYSA-N 4-(4-aminophenyl)-3-naphthalen-1-yl-n,n-diphenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1C1=CC=CC2=CC=CC=C12 RLPAWKJLZUFLCR-UHFFFAOYSA-N 0.000 description 1
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical group C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 1
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical group C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- XSHDNQUVBMNWSR-UHFFFAOYSA-N OB(C(C=CC=C1)=C1C(C1=CC=CC=C1C=C1)=C1C1=CC=CC=C1)O Chemical group OB(C(C=CC=C1)=C1C(C1=CC=CC=C1C=C1)=C1C1=CC=CC=C1)O XSHDNQUVBMNWSR-UHFFFAOYSA-N 0.000 description 1
- VKDXBZSOJFATCB-UHFFFAOYSA-N OB(C1=C(C2(C=CC3=CC=CC=C3C2)C2=CC=CC=C2)C=CC=C1)O Chemical group OB(C1=C(C2(C=CC3=CC=CC=C3C2)C2=CC=CC=C2)C=CC=C1)O VKDXBZSOJFATCB-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- HYYNZNWZEGALQN-UHFFFAOYSA-N [2-(4-methoxynaphthalen-2-yl)phenyl]boronic acid Chemical compound COC1=CC(=CC2=CC=CC=C12)C1=C(C=CC=C1)B(O)O HYYNZNWZEGALQN-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- BNASDYJRNOLPQY-UHFFFAOYSA-N iridium 2-phenylquinoline Chemical compound [Ir].c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1 BNASDYJRNOLPQY-UHFFFAOYSA-N 0.000 description 1
- NKVDKFWRVDHWGC-UHFFFAOYSA-N iridium(3+);1-phenylisoquinoline Chemical compound [Ir+3].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 NKVDKFWRVDHWGC-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- MWEKPLLMFXIZOC-UHFFFAOYSA-N pyren-1-ylboronic acid Chemical compound C1=C2C(B(O)O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 MWEKPLLMFXIZOC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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Abstract
本发明提供了可在有机电激发光元件中用作发光层的磷光主体材料、荧光主体材料、或荧光掺杂剂材料、及/或电子传输材料的有机化合物。采用该有机化合物的有机电激发光元件可以降低驱动电压、延长半衰期、或提高电流效率。
Description
技术领域
本发明是关于一种新颖的有机化合物,更具体言之是关于一种使用该有机化合物的有机电激发光元件。
背景技术
有机电激发光(有机EL)元件是一种有机发光二极体(OLED),其中发光层是由有机化合物制成的膜,有机化合物可回应电流而发光。包含有机化合物的发光层被夹置于两个电极之间。有机EL元件由于其高照度、重量轻、超薄外形、自照明而无需背光、低功耗、广视角、高对比、制造方法简单以及反应时间快速而被应用于平板显示器。
典型上,有机EL元件是由位于两个电极之间的有机材料层构成。有机材料层包括例如电洞注入层(HIL)、电洞传输层(HTL)、发光层(EML)、电子传输层(ETL)、及电子注入层(EIL)。有机电激发光的基本原理涉及载子(carrier)的注入、传输、及复合以及激子(exciton)的形成,以进行发光。当施加外部电压到有机EL元件时,电子和电洞分别从阴极和阳极注入。电子从阴极注入LUMO(最低未占用分子轨域)中,而电洞从阳极注入HOMO(最高占用分子轨域)中。随后,电子在发光层中与电洞重组而形成激子,然后激子失活而发光。当发光分子吸收能量而达到激发态时,依据电子和电洞的自旋组合,激子可呈单重态或三重态。众所周知,在电激发下形成的激子通常包括25%的单重态激子和75%的三重态激子。然而,在荧光材料中,75%的三重态激子中的电生成能量将作为热量消散,因为从三重态衰减是自旋禁阻(spin forbidden)的。因此,荧光电激发光元件仅具有25%的内部量子效率(internal quantum efficiency),导致理论上最高的外部量子效率(EQE)仅有5%,因为元件的光输出耦合效率只有约20%。相较于荧光电激发光元件,磷光有机EL元件利用自旋─轨域相互作用(spin-orbit interacttion)来促进单重态与三重态之间的系统间穿越(intersystem crossing),因此来自单重态和三重态的发光皆可取得,而且电激发光元件的内部量子效率可自25%升至100%。
对于使用有机EL元件的全彩平板显示器来说,有机EL元件中使用的有机材料在半衰期、功耗、亮度或效率方面仍然无法令人满意。因此,本发明的一个目的是提供一种新颖的有机化合物及使用该有机化合物的有机EL元件,该有机EL元件可以表现出更高的亮度或电流效率、或更长的半衰期。
发明内容
因此,本发明的一个目的是提供一种新颖的有机化合物及使用该有机化合物的有机EL元件,该有机EL元件可以表现出更高的亮度或电流效率、或更长的半衰期。
本发明的另一个目的是提供一种新颖的有机化合物及使用该有机化合物的有机EL元件,该有机EL元件能够在降低的电压下操作、或表现出更高的电流效率或更长的半衰期。
本发明的又一个目的是提供一种有机化合物,该有机化合物可在有机EL元件中用作发光层的磷光主体材料、荧光主体材料、或荧光掺杂剂材料、及/或电子传输材料,以改善功耗、亮度、电流效率、元件光色、或寿命。
依据本发明,提供一种可用于有机EL元件的有机化合物。该有机化合物是由下式(1)或式(2)表示:
其中Q1和Q2其中之一由下式(3)表示:
其中X和Y是二价桥独立选自于由O、S、Se、NR4、CR5R6、和SiR7R8所构成的群组;R1至R3独立为不存在、氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;R4为氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;以及R5至R8独立为氢原子、卤素、具有1至30个碳原子的经取代或未经取代烷基(例如甲基、乙基、正丙基、异丙基、正丁基、异丁基和叔丁基)、具有1至30个碳原子的经取代(例如被甲基取代)或未经取代芳基(例如苯基)、具有6至30个碳原子的经取代或未经取代杂芳基(例如吡啶基)、具有5至50个碳原子的经取代或未经取代芳胺基、或具有3至30个碳原子的经取代或未经取代杂芳胺基。
本发明进一步提供一种有机电激发光元件。该有机电激发光元件(有机EL元件)包含由阴极和阳极组成的电极对、及在该电极对之间的发光层及一个或多个有机薄膜层。该发光层和该有机薄膜层中的至少一个包含式(1)或式(2)的有机化合物。本发明使用式(1)或式(2)的有机化合物作为掺杂剂材料或主体材料,可使有机EL元件在相同电压下具有更高的亮度(例如1036~1506cd/m2)或电流效率(例如5.50~7.62cd/A)、或更长的半衰期(例如388~480小时)。本发明的有机EL元件使用式(1)或式(2)的有机化合物作为电子传输材料,可具有降低的驱动电压(例如4.3~5.0V)、更低的功耗、更高的电流效率(例如7.82~8.60cd/A)、更长的半衰期(例如425~560小时)。本发明的有机EL元件使用式(1)或式(2)的有机化合物作为磷光主体材料,在相同电压下可具有更高的亮度(例如880~1311cd/m2)或电流效率(例如11.19~36.22cd/A)及更长的半衰期(例如680~1136小时)。
附图说明
图1显示本发明的有机EL元件的一个实施例;图中的标号如下所示:
10透明电极 20电洞注入层
30电洞传输层 40发光层
50电子传输层 60电子注入层
70金属电极。
具体实施方式
本发明探究有机化合物及使用该有机化合物的有机电激发光元件。下面将详细说明生产、结构及组成部分,以使本发明可被充分理解。本发明的应用显然不受限于所属技术领域普通技术人员熟知的具体细节。另一方面,不对众所周知的一般组成部分和过程作详细描述,以避免对本发明造成不必要的限制。现在将在下面更详细地描述本发明的一些较佳实施例。然而,应当理解的是,除了本文明确描述的实施例之外,本发明还可实施于各种其他实施例中,也就是说,本发明还可被广泛应用于其他实施例,且本发明的范围不会因此受到明确的限制,只受随附申请专利范围的内容限制。
在本发明的一个实施例中,提供了可以在有机EL元件中用作发光层的磷光主体材料、荧光主体材料、或荧光掺杂剂材料、及/或电子传输材料的有机化合物。该有机化合物是由下式(1)或式(2)表示:
其中Q1和Q2其中之一由下式(3)表示:
其中X和Y是二价桥独立选自于由O、S、Se、NR4、CR5R6、和SiR7R8所构成的群组;R1至R3独立为不存在、氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;R4为氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;以及R5至R8独立为氢原子、卤素、具有1至30个碳原子的经取代或未经取代芳基、具有6至30个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有3至30个碳原子的经取代或未经取代杂芳胺基。
在一些实施例中,该有机化合物由下式(4)至式(11)其中之一表示:
X和Y是二价桥独立选自于由O、S、Se、NR4、CR5R6、和SiR7R8所构成的群组;R1至R3独立为不存在、氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;R4为氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;以及R5至R8独立为氢原子、卤素、具有1至30个碳原子的经取代或未经取代芳基、具有6至30个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有3至30个碳原子的经取代或未经取代杂芳胺基。
在一些实施例中,R1至R4独立为经取代或未经取代苯基、经取代或未经取代二苯基、经取代或未经取代氟基、经取代或未经取代苯并茀基、经取代或未经取代萘基、经取代或未经取代蒽基、经取代或未经取代菲基、经取代或未经取代芘基、经取代或未经取代基、经取代或未经取代三亚苯基、经取代或未经取代苯并咪唑、经取代或未经取代咔唑基、经取代或未经取代双咔唑基、经取代或未经取代二苯并喃基、经取代或未经取代二苯并噻吩基、经取代或未经取代二苯基磷氧、经取代或未经取代三嗪基、经取代或未经取代二嗪基、经取代或未经取代吡啶基、经取代或未经取代菲罗啉基、经取代或未经取代二氢吖啶基、经取代或未经取代硫二苯胺基、经取代或未经取代二氢吩嗪基、经取代或未经取代二苯胺基、经取代或未经取代三苯胺基、经取代(例如苯取代)或未经取代的喹唑啉基、经取代或未经取代的吩恶嗪基、或经取代或未经取代苯基二苯并呋喃苯胺。
在一些实施例中,R1至R4独立为由以下取代基之一所表示:
较佳地,该有机化合物为以下化合物之一:
在本发明的另一个实施例中,提供了一种有机电激发光元件。所述有机电激发光元件包含由阴极和阳极组成的一电极对、及在该电极对之间的发光层及一个或多个有机薄膜层。所述发光层和有机薄膜层中的至少一个包含式(1)或式(2)的有机化合物。
在一些实施例中,包含式(1)或式(2)的有机化合物的发光层为主体材料。所述主体材料可以是磷光主体材料或荧光主体材料。在某些实施例中,包含式(1)或式(2)的有机化合物的发光层被用作荧光掺杂剂材料。
在一些实施例中,包含式(1)或式(2)的有机化合物的有机薄膜层为电子传输层。
在本发明的另一实施例中,所述有机电激发光元件为一发光面板。在本发明的其他实施例中,所述有机电激发光元件为背光面板。
将借助以下的示例性实施例来清楚阐明本发明的有机化合物的详细制备,但本发明并不限于此等示例性实施例。实施例1至实施例15说明本发明的有机化合物的制备,而实施例16至实施例18说明有机EL元件的制造及测试报告。
实施例1
中间体A1的合成
将3g(8.4mmol)10-溴苯并[g]2.5g(10.1mmol)4,4,4',4',5,5,5',5'-八甲基-2,2'-双(1,3,2-二恶硼烷)、0.12g(0.1mmol)Pd(PPh3)4、1.0g(12.6mmol)乙酸钠、及60ml 1,4-二氧六环的混合物脱气并置于氮气下,然后在100℃下加热6小时。反应完成后,使混合物冷却至室温。随后,用乙酸乙酯和水萃取有机层,然后用无水硫酸镁干燥。将溶剂移除之后,通过硅胶管柱层析纯化残余物,得到中间体A(2.8g,85%)。
中间体A2的合成
将2g(5.0mmol)中间体A1、1.4g(5.0mmol)2,4-二溴硝基苯、0.06g(0.05mmol)Pd(PPh3)4、10ml 2M Na2CO3水溶液、10ml EtOH、及30ml甲苯的混合物脱气并置于氮气下,然后在100℃下加热12小时。反应完成后,使混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水MgSO4干燥。将溶剂移除之后,通过硅胶管柱层析纯化残余物,得到中间体A2(1.2g,50%)。
中间体A3的合成
将1g(2.1mmol)中间体A2、5.5g(21.0mmol)三苯基膦、及30ml oDCB的混合物置于氮气下,然后在180℃下加热8小时。反应完成后,使混合物冷却至室温。将混合物倒入水中,然后过滤,得到中间体A3(0.5g,50%)。
中间体A4的合成
将2.0g(4.5mmol)中间体A3、1.1g(6.7mmol)溴苯、0.05g(0.2mmol)Pd(OAc)2、0.1g(0.4mmol)三叔丁基鏻四氟硼酸盐、0.9g(9.0mmol)叔丁醇钠、及50ml甲苯的混合物脱气并置于氮气下,然后在120℃下加热16小时。反应完成后,使混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水MgSO4干燥。将溶剂移除之后,通过硅胶管柱层析纯化残余物,得到中间体A4(1.3g,55%)。MS(m/z,FAB+):523.5。
中间体A5的合成
将2g(3.8mmol)中间体A4、1.5g(5.7mmol)4,4,4',4',5,5,5',5'-八甲基-2,2'-双(1,3,2-二恶硼烷)、0.09g(0.076mmol)Pd(PPh3)4、0.7g(7.6mmol)乙酸钠、及60ml 1,4-二氧六环的混合物脱气并置于氮气下,然后在100℃下加热6小时。反应完成后,使混合物冷却至室温。随后,用乙酸乙酯和水萃取有机层,然后用无水硫酸镁干燥。将溶剂移除之后,通过硅胶管柱层析纯化残余物,得到中间体A5(1.7g,80%)。
中间体A6的合成
将2g(3.5mmol)中间体A5、1.0g(3.5mmol)2-碘苯甲酸甲酯、0.04g(0.04mmol)Pd(PPh3)4、10ml 2M Na2CO3水溶液、10ml EtOH、及30ml甲苯的混合物脱气并置于氮气下,然后在100℃下加热12小时。反应完成后,使混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水硫酸镁干燥。将溶剂移除之后,通过硅胶管柱层析纯化残余物,得到中间体A6(1.6g,82.1%)。
化合物C1的合成
在氮气下,在干燥的THF中搅拌1.6g(2.8mmol)中间体A6的同时,向其中缓慢滴加甲基溴化镁(6当量)。将混合物在室温下搅拌16小时。反应完成后,缓慢加入少量的蒸馏水,然后将混合物用乙酸乙酯萃取及用水洗涤。用无水MgSO4干燥有机层,然后移除溶剂以得到残余物。随后,将过量的磷酸溶剂(约10ml)加到残余物中,然后将其在室温下搅拌超过16小时。之后,缓慢加入蒸馏水(约50ml),然后搅拌1小时。将沉淀的固体过滤之后,用二氯甲烷溶剂萃取滤出的固体,然后用氢氧化钠水溶液洗涤。随后,取出二氯甲烷溶剂层,然后使用硫酸镁除去水分。最后,除去残余溶剂,得到化合物C1(0.6g,43%)。MS(m/z,FAB+):559.25。
实施例2
中间体A7的合成
使用与合成中间体A6相同的合成步骤,不同的是用2g中间体A1替换中间体A6、用1.4g的2,4-二溴硝基苯替换2-碘苯甲酸甲酯,以得到中间体A7(1.9g,产率=81%)。
化合物C1的合成
使用与合成化合物C1相同的合成步骤,不同的是用1.9g中间体A7替换中间体A6,以得到中间体A8(1.1g,产率=61%)。
中间体A9的合成
使用与合成中间体A1相同的合成步骤,不同的是用3g中间体A8替换10-溴苯并[g]以得到中间体A9(2.3g,产率=72.1%)。
中间体A10的合成
使用与合成中间体A2相同的合成步骤,不同的是用2g中间体A9替换中间体A1,用1.4g的1-溴硝基苯替换2,4-二溴硝基苯,以得到所要的中间体A10(1.0g,产率=53%)。
中间体A11的合成
使用与合成中间体A3相同的合成步骤,不同的是用3g中间体A10替换中间体A2,以得到所要的中间体A11(1.9g,产率=67.6%)。
化合物C2的合成
使用与合成中间体A4相同的合成步骤,不同的是用2g中间体A11替换中间体A3,以得到所要的化合物C2(1.2g,产率=53%)。
实施例3
中间体A12的合成
使用与合成中间体A2相同的合成步骤,不同的是用3g的(2-苯基萘-1-基)硼酸替换中间体A1,用2.8g的1-溴硝基苯替换2,4-二溴硝基苯,以得到所要的中间体A12(2.1g,产率=50%)。
中间体13的合成
将10g(27.8mmol)中间体A12、0.07g(0.28mmol)碘、及1000ml苯的混合物脱气并置于氮气下,然后在UV光下暴露4小时。反应完成后除去溶剂,然后将残余物再结晶3次,得到中间体A13(2.3g,23%)。
中间体A14的合成
使用与合成中间体A5相同的合成步骤,不同的是用2g中间体A13替换中间体A4,以得到所要的化合物A14(1.5g,产率=68%)。
中间体A15的合成
使用与合成中间体A7相同的合成步骤,不同的是用2g中间体A14替换中间体A1,以得到所要的化合物A15(1.6g,产率=68.3%)。
中间体A16的合成
使用与合成化合物A8相同的合成步骤,不同的是用2.5g中间体A15替换中间体A7,以得到中间体A16(1.1g,产率=42.3%)。
中间体A17的合成
使用与合成中间体A9相同的合成步骤,不同的是用2g中间体A16替换中间体A8,以得到所要的化合物A17(1.5g,产率=66.7%)。
中间体A18的合成
使用与合成中间体A10相同的合成步骤,不同的是用3g中间体A10替换中间体A17,以得到所要的中间体A18(1.6g,产率=56.2%)。
中间体A19的合成
使用与合成中间体A11相同的合成步骤,不同的是用3g中间体A18替换中间体A10,以得到所要的中间体A19(1.2g,产率=64.2%)。
化合物C4的合成
使用与合成化合物C2相同的合成步骤,不同的是用2g中间体A19替换中间体A11,以得到所要的化合物C4(1.2g,产率=53%)。
实施例4
中间体A20的合成
使用与合成中间体A12相同的合成步骤,不同的是用2g的2-(萘-2-基)苯基硼酸替换(2-苯基萘-1-基)硼酸,用1.4g的2,8-二溴二苯并[b,d]呋喃替换1,4-二溴苯,以得到所要的中间体A20(1.7g,产率=43.1%)。
中间体A21的合成
将10g(22.3mmol)中间体A20、0.07g(0.28mmol)碘、及1000ml苯的混合物脱气并置于氮气下,然后在UV光下暴露4小时。反应完成后除去溶剂,然后将残余物再结晶3次,得到中间体A21(2.3g,23%)。
中间体A22的合成
使用与合成中间体A1相同的合成步骤,不同的是用2g中间体A21替换10-溴苯并[g]以得到所要的化合物A22(1.4g,产率=63.4%)。
中间体A23的合成
使用与合成中间体A6相同的合成步骤,不同的是用3g的A22替换A5,用2g的甲基5-溴-2-碘苯甲酸甲酯替换甲基2-碘苯甲酸甲酯,以得到所要的中间体A23(2.4g,产率=78.3%)。
中间体A24的合成
使用与合成化合物C1相同的合成步骤,不同的是用2g中间体A23替换中间体A6,以得到中间体A24(0.92g,产率=48.3%)。
中间体A20的合成
使用与合成中间体A20相同的合成步骤,不同的是用2.8g的3,6-二溴-9,9-二甲基-9H-芴替换2,8-二溴二苯并[b,d]呋喃,以得到所要的中间体A25(1.7g,产率=45.1%)。
中间体26的合成
使用与合成中间体A21相同的合成步骤,不同的是用8g中间体A25替换中间体A20,以得到中间体A26(2.3g,产率=29%)。
中间体A22的合成
使用与合成中间体A1相同的合成步骤,不同的是用8g中间体A26替换10-溴苯并[g]以得到所要的化合物A27(6g,产率=68.1%)。
中间体A28的合成
使用与合成中间体A23相同的合成步骤,不同的是用6g的A27替换A22,用4.1g的1,4-二溴-2-硝基苯替换甲基5-溴-2-碘苯甲酸甲酯,以得到所要的中间体A28(3.8g,产率=54.1%)。
中间体A29的合成
使用与合成中间体A3相同的合成步骤,不同的是用5g中间体A28替换中间体A2,以得到所要的中间体A29(2.3g,产率=50%)。
中间体A30的合成
使用与合成化合物C2相同的合成步骤,不同的是用3g中间体A29替换中间体A11,以得到所要的化合物A30(1.5g,产率=43.3%)。
中间体A31的合成
使用与合成中间体A6相同的合成步骤,不同的是用6g的甲基5-溴-2-碘苯甲酸甲酯替换甲基2-碘苯甲酸甲酯,以得到所要的中间体A31(7.8g,产率=67.8%)。
中间体A32的合成
使用与合成化合物C1相同的合成步骤,不同的是用5g中间体A31替换中间体A6,以得到中间体A32(2.3g,产率=47.3%)。
中间体A33的合成
使用与合成中间体A25相同的合成步骤,不同的是用3g的2-(4-甲氧基萘-2-基)苯基硼酸替换2-(萘-2-基)苯基硼酸,以得到所要的中间体A33(2.3g,产率=43.1%)。
中间体A34的合成
使用与合成中间体A26相同的合成步骤,不同的是用8g中间体A33替换中间体A24,以得到中间体A34(1.8g,产率=30%)。
中间体A35的合成
使用与合成中间体A27相同的合成步骤,不同的是用6g中间体A34替换中间体A26,以得到所要的化合物A35(4.5g,产率=69.2%)。
中间体A36的合成
使用与合成中间体A28相同的合成步骤,不同的是用6g的中间体A35替换中间体A27,用2.2g的1-溴-2-硝基苯替换1,4-二溴-2-硝基苯,以得到所要的中间体A36(3.8g,产率=63.5%)。
中间体A37的合成
使用与合成中间体A29相同的合成步骤,不同的是用5g中间体A36替换中间体A28,以得到所要的中间体A37(2.3g,产率=48.3%)。
中间体A38的合成
使用与合成中间体A30相同的合成步骤,不同的是用4g中间体A37替换中间体A29,以得到所要的中间体A38(2.5g,产率=55.3%)。
中间体39的合成
在氮气下将3g(5.08mmol)中间体A38和二氯甲烷(60ml)的混合物放入反应器中。向其中加入三溴化硼(1当量),然后搅拌2小时,直到反应结束。用二氯甲烷和水萃取反应混合物,然后用无水MgSO4干燥。将溶剂移除得到中间体A39(2.6g,产率=89.1%)。
中间体A40的合成
在氮气下将2.6g(4.51mmol)中间体A39和二氯甲烷(60ml)的混合物放入反应器中。向其中加入吡啶(1.5当量)和三氟甲磺酸酐(1.7当量),然后搅拌12小时,直到反应结束。用二氯甲烷和水萃取反应混合物,然后用无水MgSO4干燥。将溶剂移除得到中间体A40(2.9g,产率=92.8%)。
中间体A41的合成
使用与合成中间体A35相同的合成步骤,不同的是用5g中间体A40替换中间体A34,以得到所要的化合物A41(3.4g,产率=71.2%)。
中间体A42的合成
使用与合成中间体A41相同的合成步骤,不同的是用4g中间体A32替换中间体A40,以得到所要的化合物A42(2.8g,产率=65.2%)。
中间体A43的合成
使用与合成中间体A41相同的合成步骤,不同的是用4g中间体A30替换中间体A40,以得到所要的化合物A43(3.1g,产率=72.3%)。
化合物C71的合成
将3.0g(4.7mmol)中间体A32、0.9g(5.6mmol)双苯基胺、0.04g(0.18mmol)Pd2(OAc)2、0.1g(4.47mmol)四氟硼酸三叔丁基膦、1.3g(14mmol)叔丁醇钠及60ml邻二甲苯的混合物脱气并置于氮气下,然后在150℃下加热8小时。反应完成后,使混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水MgSO4干燥。将溶剂移除之后,通过硅胶管柱层析纯化残余物,得到化合物C71(2.4g,72.3%)。MS(m/z,FAB+):726.3。
实施例5
化合物C71的合成
使用与合成化合物C71相同的合成步骤,不同的是用3g中间体A30替换中间体A32,以得到所要的化合物C72(2.4g,产率=68.3%)。MS(m/z,FAB+):754.4。
实施例6
化合物C80的合成
将1g(1.5mmol)中间体A43、1.1g(1.8mmol)2-氯-4,6-二苯基-1,3,5-三嗪、0.01g(0.03mmol)四(三苯基膦)钯、4ml的2M碳酸钠溶液、10ml乙醇、及30ml甲苯混合物脱气并置于氮气下,然后在100℃下加热12小时。反应完成后,使混合物冷却至室温。随后,用二氯甲烷和水萃取有机层,然后用无水MgSO4干燥。将溶剂移除之后,通过硅胶管柱层析纯化残余物,得到化合物C80(0.6g,53%)。MS(m/z,FAB+):790.31。
实施例7
化合物C77的合成
使用与合成化合物C80相同的合成步骤,不同的是用3g中间体A41替换中间体A43,用9-溴蒽替换2-氯-4,6-二苯基-1,3,5-三嗪,以得到所要的化合物C77(2.2g,产率=68.3%)。MS(m/z,FAB+):735.28。
实施例8
化合物C78的合成
使用与合成中间体A20相同的合成步骤,不同的是用3g中间体A24替换2,8-二溴二苯并[b,d]呋喃,不同的是用1.4g芘-1-基硼酸替换2-(萘-2-基)苯硼酸,以得到所要的化合物C78(1.8g,产率=50.3%)。
实施例9
化合物C79的合成
使用与合成中间体A36相同的合成步骤,不同的是用3g中间体A42替换A35,用1.1g2-氯-1,10-菲罗啉替换1-溴-2-硝基苯,以得到所要的化合物C79(2.1g,产率=66.2%)。MS(m/z,FAB+):737.6。
实施例10
化合物C85的合成
使用与合成化合物C71相同的合成步骤,不同的是用3g中间体A40替换中间体A32,用10H-吩恶嗪A40替换二苯胺,以得到所要的化合物C85(2.4g,产率=68.3%)。MS(m/z,FAB+):740.29。
实施例11
化合物C89的合成
使用与合化合物C80相同的合成步骤,不同的是用3g中间体A41替换A43,用1.1g的2-氯-9-苯基-1,10-菲罗啉替换2-氯-4,6-二苯基-1,3,5-三嗪,以得到所要的化合物C79(2.1g,产率=66.2%)。MS(m/z,FAB+):737.6。
实施例12
中间体A44的合成
使用与合成中间体A2相同的合成步骤,不同的是用3g的(3-苯基萘-2-基)硼酸替换中间体A1,用2.8g的1,4-二溴苯替换2,5-二溴硝基苯,以得到所要的中间体A44(2.1g,产率=50%)。
中间体34的合成
将10g(27.8mmol)中间体A44、0.07g(0.28mmol)碘、及1000ml苯的混合物脱气并置于氮气下,然后在UV光下暴露4小时。反应完成后除去溶剂,然后将残余物再结晶3次,得到中间体A45(2.3g,23%)。
中间体A46的合成
使用与合成中间体A5相同的合成步骤,不同的是用2g中间体A45替换中间体A4,以得到所要的化合物A46(1.5g,产率=68%)。
中间体A47的合成
使用与合成中间体A7相同的合成步骤,不同的是用2g的中间体A46替换中间体A1,用以得到所要的中间体A47(1.9g,产率=81.1%)。
中间体A32的合成
使用与合成中间体A8相同的合成步骤,不同的是用3g中间体A47替换中间体A7,以得到中间体A48(1.1g,产率=61.3%)。
中间体A49的合成
使用与合成中间体A9相同的合成步骤,不同的是用3g中间体A48替换中间体A8,以得到所要的化合物A49(2.3g,产率=72.1%)。
中间体A50的合成
使用与合成中间体A2相同的合成步骤,不同的是用3g的中间体A49替换中间体A27,用1.1g的1-溴-2-硝基苯替换2,4-二溴硝基苯,以得到所要的中间体A50(2.5g,产率=67.3%)。
中间体A51的合成
使用与合成中间体A3相同的合成步骤,不同的是用3g中间体A50替换中间体A2,以得到所要的中间体A51(1.9g,产率=67.6%)。
化合物C6的合成
使用与合成中间体A4相同的合成步骤,不同的是用3g中间体A51替换中间体A3,以得到所要的化合物C6(2.5g,产率=55.3%)。
中间体A2的合成
使用与合成中间体A12相同的合成步骤,不同的是用2g的(1-苯基萘-2-基)硼酸替换2-苯基萘-1-基硼酸,用1.4g的2,8-二溴二苯并[b,d]呋喃替换1,4-二溴苯,以得到所要的中间体A52(1.8g,产率=45.9%)。
中间体A53的合成
将10g(22.3mmol)中间体A52、0.06g(0.23mmol)碘、及1000ml苯的混合物脱气并置于氮气下,然后在UV光下暴露4小时。反应完成后除去溶剂,然后将残余物再结晶3次,得到中间体A53(2.1g,21%)。
中间体A54的合成
使用与合成中间体A17相同的合成步骤,不同的是用2g中间体A53替换A16,以得到所要的化合物A54(1.3g,产率=59.1%)。
中间体A55的合成
使用与合成中间体A6相同的合成步骤,不同的是用3g的A54替换A5,以得到所要的中间体A55(2.5g,产率=81.7%)。
C21的合成
使用与合成化合物C1相同的合成步骤,不同的是用2g中间体A55替换中间体A6,以得到化合物C21(0.85g,产率=44.1%)。
实施例14
中间体A56的合成
使用与合成中间体A12相同的合成步骤,不同的是用2g的2-(萘基-1-基)苯硼酸替换(2-苯基萘-1-基)苯硼酸,用1.4g的2,8-二溴二苯并[b,d]呋喃替换1,4-二溴苯,以得到所要的中间体A56(1.7g,产率=43.4%)。
中间体A57的合成
将10g(22.3mmol)中间体A56、0.06g(0.23mmol)碘、及1000ml苯的混合物脱气并置于氮气下,然后在UV光下暴露4小时。反应完成后除去溶剂,然后将残余物再结晶3次,得到中间体A57(2.2g,22%)。
中间体A58的合成
使用与合成中间体A17相同的合成步骤,不同的是用2g中间体A57替换中间体A16,以得到所要的化合物A58(1.5g,产率=68.2%)。
中间体A59的合成
使用与合成中间体A6相同的合成步骤,不同的是用3g的中间体A58替换中间体A5,用以得到所要的中间体A59(2.3g,产率=75.2%)。
C24的合成
使用与合成化合物C1相同的合成步骤,不同的是用2g中间体A59替换中间体A6,以得到化合物C24(0.88g,产率=45.6%)。
中间体A60的合成
使用与合成中间体A12相同的合成步骤,不同的是用2g的2-(萘基-2-基)苯硼酸替换(2-苯基萘-2-基)苯硼酸,用1.4g的2,8-二溴二苯并[b,d]呋喃替换1,4-二溴苯,以得到所要的中间体A56(1.7g,产率=43.4%)。
中间体A61的合成
将10g(22.2mmol)中间体A60、0.06g(0.23mmol)碘、及1000ml苯的混合物脱气并置于氮气下,然后在UV光下暴露4小时。反应完成后除去溶剂,然后将残余物再结晶3次,得到中间体A61(2.3g,23%)。
中间体A62的合成
使用与合成中间体A17相同的合成步骤,不同的是用2g中间体A61替换中间体A16,以得到所要的化合物A62(1.3g,产率=59.1%)。
中间体A63的合成
使用与合成中间体A6相同的合成步骤,不同的是用3g的中间体A62替换中间体A5,用以得到所要的中间体A63(2.4g,产率=80%)。
C25的合成
使用与合成化合物C1相同的合成步骤,不同的是用2g中间体A63替换中间体A6,以得到化合物C25(0.78g,产率=40.1%)。
生产有机电激发光元件的一般方法
提供阻值为12欧姆/平方(ohm/square)及厚度为120nm的铟锡氧化物涂层玻璃(以下称为ITO基板),并在超声波浴(例如洗涤剂、去离子水)中进行多步骤清洗。在气相沉积有机层之前,通过紫外光(UV)和臭氧进一步处理清洗过的ITO基板。ITO基板的所有预处理过程都在洁净室(100级)内进行。
在高真空设备下(10-7Torr)利用电阻加热的石英舟以气相沉积将这些有机层依序涂布到ITO基板上。借助石英晶体监视器来精确监控或设定各层的厚度和气相沉积速率(0.1~0.3nm/sec)。如上所述,还可以使个别层包含不只一种化合物,即通常掺杂有掺杂剂材料的主体材料。此可通过来自两个或多个来源的共气相沉积成功地实现,表示本发明的有机化合物是热稳定的。
使用二吡嗪并[2,3-f:2',3'-h]喹喔啉-2,3,6,7,10,11-六腈(dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile)(HAT-CN)形成电洞注入层,并使用N,N-双(萘-1-基)-N,N-双(苯基)-联苯胺(NPB)形成有机EL元件的电洞传输层。使用2,9-双(萘-2-基)-4,7-二苯基-1,10-啡啉(NPhen)作为有机EL元件的电子传输材料,因其相较于BPhen或BCP具有更高的热稳定性和更长的寿命。对于荧光发光元件,使用1,1'-(9,9-二甲基-9H-芴-2,7-二基)二芘(DFDP)作为主体材料,并使用(E)-6-(4-(二苯基胺基)苯乙烯基)-N,N-二苯基萘-2-胺(D1)作为荧光掺杂剂。对于磷光发光元件,使用双(2-甲基-8-羟基喹啉)-4-(苯基苯酚)铝(BAlq)作为发光层的主体材料,并使用三(1-苯基异喹啉)铱(III)(Ir(piq)3)或三(2-苯基喹啉)铱(III)(Ir(2-phq)3)作为掺杂剂材料。使用化合物C77和C78作为荧光主体材料来与DFDP比较。使用中间体C71、C72、及C85作为荧光掺杂剂材料来与D1比较。使用化合物C79、C80、及C89作为电子传输材料来与NPhen比较。使用化合物C1、C2、C4、C6、C21、C24、及C25作为磷光主体材料来与BAlq比较。本发明中用于制作对照和例示性有机EL元件的传统OLED材料和本发明的例示性有机化合物的化学结构如下所示:
有机EL元件一般包含通过热蒸发形成为阴极的低功函数金属,例如Al、Mg、Ca、Li及K,且该低功函数金属可有助于电子从阴极注入电子传输层。另外,在阴极与电子传输层之间引入薄膜电子注入层,用于降低电子注入阻障并改善有机EL元件的性能。习知的电子注入层材料为具有低功函数的金属卤化物或金属氧化物,例如:LiF、MgO、或Li2O。
另一方面,在制作有机EL元件之后,通过使用PR650光谱扫描光谱仪量测EL光谱及CIE座标。此外,使用吉时利(Keithley)2400可程式化电压电流源测得电流/电压、亮度/电压、及效率/电压特性。在室温(约25℃)及大气压下操作上述设备。
实施例16
使用与上述一般方法类似的过程制作发射蓝色荧光并具有以下如图1所示元件结构的有机EL元件,由下而上各层分别是:ITO/HAT-CN(20nm)/NPB(50nm)/蓝色荧光主体(DFDP或C77或C78)+5%掺杂剂(D1或C71、C72、或C85)(30nm)/NPhen(30nm)/LiF(0.5nm)/Al(160nm)。在图1所示的元件中,将电洞注入层(HIL)20(HAT-CN)沉积到透明电极10(ITO)上,将电洞传输层(HTL)30沉积到电洞注入层20上,将发光层40(掺杂的主体)沉积到电洞传输层30(NPB)上,将电子传输层(ETL)50沉积到发光层40(蓝色荧光主体+5%掺杂剂)上,将电子注入层(EIL)60沉积到电子传输层50上,将金属电极层70(Al)沉积到电子注入层60上。将这些有机EL元件的I-V-B(1000尼特亮度时)和半衰期测试报告总结于下表1。半衰期的定义为3000cd/m2的初始亮度降至一半的时间。
表1
根据上述有机EL元件的测试报告总结,显而易见的是,用作蓝色荧光主体或掺杂剂材料的式(1)或式(2)有机化合物表现出比现有技术的材料更佳的性能。具体来说,本发明使用式(1)或式(2)的有机化合物作为掺杂剂材料或主体材料来与主体材料DFDP或掺杂剂材料D1搭配的有机EL元件在相同电压下具有更高的亮度或电流效率、或更长的半衰期。
实施例17
使用与上述一般方法类似的过程制作具有以下如图1所示元件结构的有机EL元件,由下而上各层分别是:ITO/HAT-CN(20nm)/NPB(50nm)/DFDP+5%D1(30nm)/NPhen或C79、C80、或C89(30nm)/LiF(0.5nm)/Al(160nm)。将此等发射蓝色荧光的有机EL元件的I-V-B和半衰期测试报告总结于下表2,并将半衰期定义为3000cd/m2的初始亮度降低一半的时间。
表2
根据上述有机EL元件的测试报告总结,显而易见的是,用作电子传输材料的式(1)或式(2)有机化合物表现出比现有技术的材料NPhen更佳的性能。具体来说,本发明的有机EL元件使用式(1)或式(2)的有机化合物作为电子传输材料来与主体材料DFDP和掺杂剂材料D1搭配可具有更低的功耗、更高的电流效率、或更长的半衰期。
实施例18
使用与上述一般方法类似的过程制作发射磷光并具有以下如图1所示元件结构的有机EL元件,由下而上各层分别是:ITO/HAT-CN(20nm)/NPB(50nm)/磷光主体(C1、C2、C4)+10%掺杂剂(30nm)/NPhen(30nm)/LiF(0.5nm)/Al(160nm)。将这些发射磷光的有机EL元件的I-V-B和半衰期测试报告总结于下表3,并将半衰期定义为3000cd/m2的初始亮度降低一半的时间。
表3
根据上述有机EL元件的测试报告总结,显而易见的是,用作磷光主体材料的式(1)或式(2)有机化合物表现出比现有技术的材料BAlq更佳的性能。具体来说,本发明的有机EL元件使用式(1)或式(2)的有机化合物作为磷光主体材料来与掺杂剂材料Ir(piq)3或Ir(2-phq)3搭配在相同电压下可具有更高的亮度或电流效率或更长的半衰期。
总而言之,本发明提供了有机化合物,该有机化合物可在有机EL元件中用作发光层的磷光主体材料、荧光主体材料、或荧光掺杂剂材料、或电子传输材料。所述的有机化合物是由下式(1)或式(2)表示:
其中Q1和Q2其中之一是由下式(3)表示:
其中X和Y是二价桥独立选自于由O、S、Se、NR4、CR5R6、和SiR7R8所构成的群组;R1至R3独立为不存在、氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;R4为氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;以及R5至R8独立为氢原子、卤素、具有1至30个碳原子的经取代或未经取代芳基、具有6至30个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有3至30个碳原子的经取代或未经取代杂芳胺基。
根据上述教示显然可以作出许多的修改及变化。因此,应当了解的是,在随附申请专利范围的范围内,可以以本文具体描述的方式以外的其他方式来实施本发明。虽然,本文中已说明并描述了具体实施例,但对于所属技术领域中具有通常知识者来说,显而易见的是可以在不偏离欲单独由随附申请专利范围限制的情况下对本发明作出许多修改。
Claims (10)
1.一种以下式(1)或式(2)表示的有机化合物:
其中Q1和Q2其中之一是由下式(3)表示:
其中X和Y是二价桥独立选自于由O、S、Se、NR4、CR5R6、和SiR7R8所构成的群组;R1至R3独立为不存在、氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;R4为氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;以及R5至R8独立为氢原子、卤素、甲基、具有1至30个碳原子的经取代或未经取代芳基、具有6至30个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有3至30个碳原子的经取代或未经取代杂芳胺基。
2.如权利要求1所述的有机化合物,其中该有机化合物是由下式(4)至式(11)其中之一表示:
X和Y是二价桥独立选自于由O、S、Se、NR4、CR5R6、和SiR7R8所构成的群组;R1至R3独立为不存在、氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;R4为氢原子、卤素、具有5至50个碳原子的经取代或未经取代芳基、具有5至50个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有5至50个碳原子的经取代或未经取代杂芳胺基;以及R5至R8独立为氢原子、卤素、具有1至30个碳原子的经取代或未经取代芳基、具有6至30个碳原子的经取代或未经取代杂芳基、具有5至50个碳原子的经取代或未经取代芳胺基、或具有3至30个碳原子的经取代或未经取代杂芳胺基。
3.如权利要求1所述的有机化合物,其中R1至R4独立为经取代或未经取代苯基、经取代或未经取代二苯基、经取代或未经取代氟基、经取代或未经取代苯并茀基、经取代或未经取代萘基、经取代或未经取代蒽基、经取代或未经取代菲基、经取代或未经取代芘基、经取代或未经取代基、经取代或未经取代三亚苯基、经取代或未经取代苯并咪唑、经取代或未经取代咔唑基、经取代或未经取代双咔唑基、经取代或未经取代二苯并喃基、经取代或未经取代二苯并噻吩基、经取代或未经取代二苯基磷氧、经取代或未经取代三嗪基、经取代或未经取代二嗪基、经取代或未经取代吡啶基、经取代或未经取代菲罗啉基、经取代或未经取代二氢吖啶基、经取代或未经取代硫二苯胺基、经取代或未经取代二氢吩嗪基、经取代或未经取代二苯胺基、经取代或未经取代三苯胺基、或经取代或未经取代苯基二苯并呋喃苯胺。
4.如权利要求1所述的有机化合物,R1至R4独立为由以下取代物其中之一所表示:
5.如权利要求1所述的有机化合物,其中该有机化合物是下列化合物其中之一:
6.一种有机电激发光元件,包含由阴极和阳极组成的电极对、及在所述电极对之间的发光层及一个或多个有机薄膜层,其中所述发光层和有机薄膜层中的至少一个包含如权利要求1所述的有机化合物。
7.如权利要求6所述的有机电激发光元件,其中包含式(1)或式(2)的有机化合物的发光层为主体材料。
8.如权利要求6所述的有机电激发光元件,其中包含式(1)或式(2)的有机化合物的发光层为荧光掺杂剂材料。
9.如权利要求6所述的有机电激发光元件,其中包含式(1)或式(2)的有机化合物的有机薄膜层为电子传输层。
10.如权利要求6所述的有机电激发光元件,其中所述有机电激发光元件为发光面板或背光面板。
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