CN116368118A - 金刚烷化合物、有机电致发光元件和电子设备 - Google Patents
金刚烷化合物、有机电致发光元件和电子设备 Download PDFInfo
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- CN116368118A CN116368118A CN202180068860.7A CN202180068860A CN116368118A CN 116368118 A CN116368118 A CN 116368118A CN 202180068860 A CN202180068860 A CN 202180068860A CN 116368118 A CN116368118 A CN 116368118A
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- adamantane compound
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- -1 Adamantane compound Chemical class 0.000 title claims abstract description 101
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 239000010410 layer Substances 0.000 claims abstract description 150
- 239000000463 material Substances 0.000 claims abstract description 46
- 239000011247 coating layer Substances 0.000 claims abstract description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000010409 thin film Substances 0.000 claims description 19
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000000470 constituent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 47
- 238000000605 extraction Methods 0.000 abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 2
- 239000010408 film Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 20
- 238000007740 vapor deposition Methods 0.000 description 20
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 238000002156 mixing Methods 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 12
- 238000010586 diagram Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000002356 single layer Substances 0.000 description 8
- 238000004528 spin coating Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 125000006617 triphenylamine group Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 5
- RJZYHCVSHJVDHT-UHFFFAOYSA-N O=C(C(C=C1)=CC=C1F)NC(CC(C1)C2)(CC1C1)CC21NC(C(C=C1)=CC=C1F)=O Chemical compound O=C(C(C=C1)=CC=C1F)NC(CC(C1)C2)(CC1C1)CC21NC(C(C=C1)=CC=C1F)=O RJZYHCVSHJVDHT-UHFFFAOYSA-N 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 3
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-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
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical compound C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- OYZWEOORLJBPMA-UHFFFAOYSA-N 3,5-difluorobenzoyl chloride Chemical group FC1=CC(F)=CC(C(Cl)=O)=C1 OYZWEOORLJBPMA-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
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- MZYDBGLUVPLRKR-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 MZYDBGLUVPLRKR-UHFFFAOYSA-N 0.000 description 1
- QJZJIWYDCCBNTH-UHFFFAOYSA-N 9-[4-(9H-fluoren-1-yl)phenyl]carbazole Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C1=2)C1=CC=C(C=C1)C1=CC=CC=2C3=CC=CC=C3CC1=2 QJZJIWYDCCBNTH-UHFFFAOYSA-N 0.000 description 1
- FOUNKDBOYUMWNP-UHFFFAOYSA-N 9-[4-[2-(4-carbazol-9-ylphenyl)-2-adamantyl]phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C1(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C(C2)CC3CC1CC2C3 FOUNKDBOYUMWNP-UHFFFAOYSA-N 0.000 description 1
- 229910000882 Ca alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 101000860173 Myxococcus xanthus C-factor Proteins 0.000 description 1
- MTXXVAWDCAPBMP-UHFFFAOYSA-N O=C(C(C(F)=C(C(F)=C1F)F)=C1F)NC(CC(C1)C2)(CC1C1)CC21NC(C(C(F)=C(C(F)=C1F)F)=C1F)=O Chemical compound O=C(C(C(F)=C(C(F)=C1F)F)=C1F)NC(CC(C1)C2)(CC1C1)CC21NC(C(C(F)=C(C(F)=C1F)F)=C1F)=O MTXXVAWDCAPBMP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- FUHDUDFIRJUPIV-UHFFFAOYSA-N [4-[9-(4-carbazol-9-ylphenyl)fluoren-9-yl]phenyl]-triphenylsilane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C1(C2=CC=CC=C2C2=CC=CC=C21)C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)(C=1C=CC=CC=1)C1=CC=CC=C1 FUHDUDFIRJUPIV-UHFFFAOYSA-N 0.000 description 1
- JZXXUZWBECTQIC-UHFFFAOYSA-N [Li].C1=CC=CC2=NC(O)=CC=C21 Chemical compound [Li].C1=CC=CC2=NC(O)=CC=C21 JZXXUZWBECTQIC-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- FOLJMFFBEKONJP-UHFFFAOYSA-N adamantane-1,3-diamine Chemical compound C1C(C2)CC3CC1(N)CC2(N)C3 FOLJMFFBEKONJP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-N aluminum;2-methylquinolin-8-ol;4-phenylphenol 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-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
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- 230000005540 biological transmission Effects 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- ZFXVRMSLJDYJCH-UHFFFAOYSA-N calcium magnesium Chemical compound [Mg].[Ca] ZFXVRMSLJDYJCH-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
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- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
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Abstract
本发明的目的在于,为了改善有机EL元件的光取出效率而提供适合于覆盖层中的低折射率层的化合物。本发明着眼于金刚烷化合物的薄膜稳定性优异这一点,并发现:在中心配置有金刚烷的酰胺化合物、酯化合物、胺化合物或醚化合物显示出低折射率特性,通过作为构成低折射率覆盖层的材料而加以使用,从而得到发光效率优异的有机EL元件。
Description
技术领域
本发明涉及适合于各种显示装置的自发光元件、即有机电致发光元件(以下简称为有机EL元件)或适合于电子设备的化合物和元件,详细而言,涉及金刚烷化合物和使用该化合物得到的有机EL元件或电子设备。
背景技术
伊士曼柯达公司的C.W.Tang等人在1987年通过开发将各种作用分担于各种材料而得到的层叠结构元件,从而将使用了有机材料的有机EL元件加以实用。他们通过将能够输送电子的荧光体与能够输送空穴的有机物进行层叠,并将两种电荷注入至荧光体的层中而使其发光,从而以10V以下的电压得到了1000cd/m2以上的高亮度(参照专利文献1和专利文献2)。
近年来,逐渐使用将具有高功函数的金属用于阳极且从上部发光的顶部发光结构的发光元件。在从具有像素电路的底部取出光的底部发光结构中,发光部的面积受到限制,与此相对,在顶部发光结构的发光元件中,通过从上部取出光,从而像素电路不会发生遮挡,因此,存在能够扩大发光部的优点。在顶部发光结构的发光元件中,阴极使用LiF/Al/Ag(例如参照非专利文献1)、Ca/Mg(参照非专利文献2)、LiF/MgAg等半透明电极。
在这种发光元件中,由发光层发出的光向其它膜入射的情况下,若以某种角度以上入射,则会被发光层与其它膜的界面全反射。因此,仅能够利用所发出的光的一部分。近年来,为了提高光的取出效率,提出了在折射率低的半透明电极的外侧设置有折射率高的“覆盖层”的发光元件(例如参照非专利文献1和2)。
另一方面,示出一种有机光学设备,其通过共蒸镀添加物而形成低折射率层,通过与高折射率层进行层叠而活用光干涉的效果,并形成进行了有效的光传播控制的多层膜(参照专利文献3)。
已知的是:通过形成折射率高的覆盖层,从而提高有机EL元件的光取出效率,但为了形成低折射率层而如专利文献3中记载的那样,与添加物进行了共蒸镀,寻求能够单独进行低温蒸镀的化合物。
现有技术文献
专利文献
专利文献1:日本特开平8-048656号公报
专利文献2:日本特许第3194657号公报
专利文献3:日本特许第6210473号公报
非专利文献1:Appl.Phys.Let.,78,544(2001)
非专利文献2:Appl.Phys.Let.,82,466(2003)
发明内容
发明要解决的问题
本发明的目的在于,为了改善有机EL元件的光取出效率而提供适合于覆盖层中的低折射率层的化合物。
作为适合于本发明的低折射率层的材料的物理特性,可列举出:(1)能够蒸镀且不发生热分解;(2)薄膜状态稳定;(3)折射率低。另外,作为适合于本发明的元件的物理特性,可列举出:(1)光的取出效率高;(2)色纯度不会降低;(3)透光而不会发生经时变化;(4)长寿命。
用于解决问题的方案
本发明人等为了实现上述目的而着眼于金刚烷化合物的薄膜稳定性优异这一点,并发现:在中心配置有金刚烷的酰胺化合物、酯化合物、胺化合物或醚化合物显示出低折射率特性,将其用作构成低折射率覆盖层的材料来制作有机EL元件,并深入进行元件的特性评价的结果,从而完成了本发明。
即,根据本发明,提供以下的金刚烷化合物和有机EL元件。
1)一种金刚烷化合物,其用下述通式(1)表示。
(式中,X表示氧原子或NH基;L表示碳原子数1~3的直链状或支链状的亚烷基或羰基;R1、R2任选彼此相同或不同,表示取代或未取代的芳香族烃基。)
2)根据上述1)所述的金刚烷化合物,其中,前述金刚烷化合物用下述通式(1-A)表示。
(式中,X和L如前述通式(1)中定义的那样。R3~R12任选彼此相同或不同,表示氢原子、卤素原子、氰基、取代或未取代的碳原子数1~3的直链状或支链状的烷基、取代或未取代的碳原子数1~3的直链状或支链状的烷氧基、或者取代或未取代的芳香族烃基。)
3)根据上述1)或2)所述的金刚烷化合物,其中,前述金刚烷化合物用下述通式(1-B)表示。
(式中,R3~R12如前述通式(1-A)中定义的那样。)
4)根据上述1)或2)所述的金刚烷化合物,其中,前述金刚烷化合物用下述通式(1-C)表示。
(式中,R3~R12如前述通式(1-A)中定义的那样。)
5)根据上述1)或2)所述的金刚烷化合物,其中,前述金刚烷化合物用下述通式(1-D)表示。
(式中,R3~R12如前述通式(1-A)中定义的那样。)
6)根据上述1)或2)所述的金刚烷化合物,其中,前述金刚烷化合物用下述通式(1-E)表示。
(式中,R3~R12如前述通式(1-A)中定义的那样。)
7)一种有机薄膜,其特征在于,其包含上述1)~6)中任一项所述的金刚烷化合物,所述有机薄膜在波长400nm~700nm的范围内的折射率为1.60以下。
8)一种有机EL元件,其特征在于,其至少依次具有阳极电极、空穴输送层、发光层、电子输送层、阴极电极和覆盖层,前述覆盖层为上述7)所述的有机薄膜。
9)一种有机EL元件,其特征在于,其至少依次具有阳极电极、空穴输送层、发光层、电子输送层、阴极电极和覆盖层,前述覆盖层为第一覆盖层和第二覆盖层的二层结构,第一覆盖层为上述7)所述的有机薄膜。
10)根据上述9)所述的有机EL元件,其特征在于,前述第一覆盖层的折射率与第二覆盖层的折射率之差([第二覆盖层的折射率]-[第一覆盖层的折射率])为0.2以上。
11)一种电子设备或电子元件,其特征在于,其具有一对电极和夹在其间的至少一层有机层,前述有机层使用上述1)~6)中任一项所述的金刚烷化合物作为其构成材料。
本说明书中,记作“取代或未取代”时的“未取代”是指氢原子未被取代基取代。
本说明书中,“氢原子”是指中子数不同的同位素,即,以包括氕、氘在内的含义来使用。
作为通式(1)中的L所示的“碳原子数1~3的直链状或支链状的亚烷基”中的“亚烷基”,具体而言,可列举出亚甲基、1,2-亚乙基、1,3-亚丙基,优选为亚甲基、1,2-亚乙基,更优选为亚甲基。
另外,这些二价基团优选未取代,也可以具有取代基,作为此时的取代基,具体而言,可列举出氰基;氟原子、氯原子、溴原子、碘原子等卤素原子;甲氧基、乙氧基、丙氧基等碳原子数1~3的直链状或支链状的烷氧基等。
通式(1)中的X表示氧原子或NH基。
具体而言,在通式(1)中的X为氧原子且L为亚烷基的情况下,前述通式(1)中的(-L-X-)为醚基,在通式(1)中的X为氧原子且L为羰基的情况下,前述通式(1)中的(-L-X-)为酯基。
并且,在通式(1)中的X为NH基且L为亚烷基的情况下,前述通式(1)中的(-L-X-)为氨基,在通式(1)中的X为NH基且L为羰基的情况下,前述通式(1)中的(-L-X-)为酰胺基。
作为通式(1)中的R1、R2所示的“取代或未取代的芳香族烃基”中的“芳香族烃基”,具体而言,可列举出苯基、联苯基、1-萘基、2-萘基、2-菲基、9-菲基、芴基,优选为苯基、联苯基、1-萘基、2-萘基、芴基,更优选为苯基、芴基。
另外,这些基团可以具有取代基,作为此时的取代基,具体而言,可列举出氰基;氟原子、氯原子、溴原子、碘原子等卤素原子;甲基、乙基、丙基等碳原子数1~3的直链状或支链状的烷基;甲氧基、乙氧基、丙氧基等碳原子数1~3的直链状或支链状的烷氧基;苯基、联苯基、1-萘基、2-萘基、芴基等芳香族烃基等。
作为通式(1-A)中的R3~R12所示的“卤素原子”,可列举出氟原子、氯原子、溴原子、碘原子,优选为氟原子、氯原子,更优选为氟原子。
作为通式(1-A)中的R3~R12所示的“取代或未取代的碳原子数1~3的直链状或支链状的烷基”中的“烷基”,可列举出甲基、乙基、丙基,优选为甲基、乙基,更优选为甲基。
作为通式(1-A)中的R3~R12所示的“取代或未取代的碳原子数1~3的直链状或支链状的烷氧基”中的“烷氧基”,可列举出甲氧基、乙氧基、丙氧基,优选为甲氧基、乙氧基,更优选为甲氧基。
作为通式(1-A)中的R3~R12所示的“取代或未取代的芳香族烃基”中的“芳香族烃基”,具体而言,可列举出苯基、联苯基、1-萘基、2-萘基、2-菲基、9-菲基、芴基,优选为苯基、联苯基、1-萘基、2-萘基、芴基,更优选为苯基、芴基,进一步优选为苯基。
另外,这些基团可以具有取代基,作为此时的取代基,具体而言,可列举出氰基;氟原子、氯原子、溴原子、碘原子等卤素原子;甲基、乙基、丙基等碳原子数1~3的直链状或支链状的烷基;甲氧基、乙氧基、丙氧基等碳原子数1~3的直链状或支链状的烷氧基等。
通式(1-A)中的R3~R12所示的“碳原子数1~3的直链状或支链状的烷基”和“碳原子数1~3的直链状或支链状的烷氧基”可以具有取代基,作为此时的“取代基”,优选为卤素原子,更优选为氟原子。
本发明的通式(1)所示的金刚烷化合物优选为下述通式(1-A)~(1-E)中任一者所示的金刚烷化合物,更优选为下述通式(1-B)~(1-E)中任一者所示的金刚烷化合物。
通式(1)中的两个L优选为相同的基团,也可以为不同的基团。
另外,通式(1)中的两个X优选为相同的基团,也可以为不同的基团。
另外,在通式(1)中,R1、R2彼此可以相同也可以不同,优选相同。
通式(1-A)~(1-E)中,X表示氧原子或NH基,L表示碳原子数1~3的直链状或支链状的亚烷基、或者羰基。
R3~R12任选彼此相同或不同,为氢原子、卤素原子、氰基、取代或未取代的碳原子数1~3的直链状或支链状的烷基、取代或未取代的碳原子数1~3的直链状或支链状的烷氧基、或者取代或未取代的芳香族烃基。
碳原子数1~3的直链状或支链状的亚烷基、芳香族烃基、卤素原子、碳原子数1~3的直链状或支链状的烷基、碳原子数1~3的直链状或支链状的烷氧基和它们的取代基等的详情如上所述。
发明的效果
本发明的通式(1)所示的金刚烷化合物的低折射率特性优异。由此,通过使用该化合物来形成低折射率层(有机薄膜),并与高折射率层(有机薄膜)加以组合,从而实现利用光干涉效果进一步改善光取出效率的有机EL元件。
另外,本发明的金刚烷化合物不仅可利用于有机EL元件,还可用于电子照片感光体、图像传感器、光电转换元件、太阳能电池等电子设备领域。
附图说明
图1是作为本发明的通式(1)所示的金刚烷化合物而示出化合物(1-1)~(1-16)的结构的图。
图2是作为本发明的通式(1)所示的金刚烷化合物而示出化合物(1-17)~(1-32)的结构的图。
图3是作为本发明的通式(1)所示的金刚烷化合物而示出化合物(1-33)~(1-50)的结构的图。
图4是作为本发明的通式(1)所示的金刚烷化合物而示出化合物(1-51)~(1-68)的结构的图。
图5是作为本发明的通式(1)所示的金刚烷化合物而示出化合物(1-69)~(1-86)的的图。
图6是作为本发明的通式(1)所示的金刚烷化合物而示出化合物(1-87)~(1-104)的结构的图。
图7是作为本发明的通式(1)所示的金刚烷化合物而示出化合物(1-105)~(1-122)的结构的图。
图8是作为本发明的通式(1)所示的金刚烷化合物而示出化合物(1-123)~(1-140)的结构的图。
图9是作为适合在本发明的有机EL元件中使用的高折射率的芳基胺化合物的具体例而示出化合物(2-1)~(2-10)的结构的图。
图10是作为适合在本发明的有机EL元件中使用的高折射率的芳基胺化合物的具体例而示出化合物(2-11)~(2-18)的结构的图。
图11是示出实施例6~8、比较例1~2的有机EL元件构成的图。
具体实施方式
本发明的通式(1)所示的金刚烷化合物为新型化合物,但这些化合物其自身可按照公知方法来合成。
将本发明的通式(1)所示的金刚烷化合物的具体例示于图1~图8,但不限定于这些化合物。
将适合在本发明的有机EL元件中使用的高折射率的芳基胺化合物的具体例示于图9~图10,但不限定于这些化合物。
本发明的通式(1)所示的金刚烷化合物的制造方法没有特别限定,化合物的精制可通过基于柱色谱的精制、基于硅胶、活性炭、活性白土等的吸附精制、基于溶剂的重结晶、晶析等在有机化合物的精制中使用的公知方法来进行,最终利用升华精制法等来进行精制。化合物的鉴定可通过NMR分析、质谱分析等来进行。作为物性值,优选进行熔点、玻璃化转变温度(Tg)、折射率、吸光度的测定。
熔点和玻璃化转变温度(Tg)通过例如使用粉体并利用高灵敏度差示扫描量热计(BRUKER-AXS公司制、DSC3100SA)进行测定。
折射率通过在硅基板上制作80nm的薄膜,并使用分光测定装置(FILMETRICS公司制、F10-RT-UV)进行测定。
作为本发明的有机EL元件的结构,例如,在顶部发光结构的发光元件的情况下,可列举出:在玻璃基板上依次包含阳极、空穴输送层、发光层、电子输送层、阴极和覆盖层的结构;另外,在阳极与空穴输送层之间具有空穴注入层的结构;在空穴输送层与发光层之间具有电子阻挡层的结构;在发光层与电子输送层之间具有空穴阻挡层的结构;在电子输送层与阴极之间具有电子注入层的结构。这些多层结构中,有机层可以省略几层或兼用几层,例如,也可以制成兼作空穴注入层和空穴输送层的构成、兼作空穴输送层和电子阻挡层的构成、兼作空穴阻挡层和电子输送层的构成、兼作电子输送层和电子注入层的构成等。另外,可以制成将具有相同功能的有机层层叠2层以上而得到的构成,也可以制成将空穴输送层层叠2层而得到的构成、将发光层层叠2层而得到的构成、将电子输送层层叠2层而得到的构成、将覆盖层层叠2层而得到的构成等。
有机EL元件的各层的总膜厚优选为200nm~750nm左右,更优选为350nm~600nm左右。另外,覆盖层的膜厚例如优选为30nm~120nm,更优选为40nm~80nm。在该情况下,能够得到良好的光取出效率。需要说明的是,覆盖层的膜厚可根据发光元件中使用的发光材料的种类、除覆盖层之外的有机EL元件的各层的厚度等来适当变更。
作为本发明的有机EL元件的阳极,可使用ITO、金之类的功函数大的电极材料。
作为本发明的有机EL元件的空穴注入层,优选为在分子中具有将2个以上的三苯基胺结构借助单键或不含杂原子的二价基团进行连接而得到的结构的芳基胺化合物;例如联苯胺衍生物等在分子中具有将2个三苯基胺结构借助单键或不含杂原子的二价基团进行连接而得到的结构的芳基胺化合物;星型的三苯基胺衍生物;各种三苯基胺四聚体等材料。另外,可以使用以铜酞菁为代表的卟啉化合物、六氰基氮杂苯并菲之类的受体性杂环化合物、涂布型的高分子材料。它们可以单独成膜,也可以以与其它材料混合成膜而得到的单层的形式加以使用,还可以制成单独成膜的层彼此的层叠结构、混合成膜的层彼此的层叠结构、或者单独成膜的层与混合成膜的层的层叠结构。这些材料除了蒸镀法之外,也可以利用旋涂法、喷墨法等公知方法来进行薄膜形成。
作为本发明的有机EL元件的空穴输送层,优选使用N,N’-二苯基-N,N’-二(间甲苯基)联苯胺(TPD)、N,N’-二苯基-N,N’-二(α-萘基)联苯胺(NPD)、N,N,N’,N’-四联苯基联苯胺等联苯胺衍生物;1,1-双[4-(二-4-甲苯基氨基)苯基]环己烷(TAPC),特别优选使用在分子中具有将2个三苯基胺结构借助单键或不含杂原子的二价基团进行连接而得到的结构的芳基胺化合物,例如N,N,N’,N’-四联苯基联苯胺等。另外,优选使用在分子中仅具有1个三苯基胺结构的芳基胺化合物、在分子中具有将3个以上的三苯基胺结构借助单键或不含杂原子的二价基团进行连接而得到的结构的芳基胺化合物、例如各种三苯基胺三聚体和四聚体等。它们可以单独成膜,也可以以与其它材料混合成膜而得到的单层的形式加以使用,还可以制成单独成膜的层彼此的层叠结构、混合成膜的层彼此的层叠结构、或者单独成膜的层与混合成膜的层的层叠结构。另外,作为空穴的注入/输送层,可以使用聚(3,4-乙烯二氧噻吩)(PEDOT)/聚(苯乙烯磺酸盐)(PSS)等涂布型的高分子材料。这些材料除了蒸镀法之外,也可以利用旋涂法、喷墨法等公知方法来进行薄膜形成。
另外,在空穴注入层或空穴输送层中,优选对该层中通常使用的材料进一步p掺杂三溴苯基胺六氯化锑、轴烯衍生物等。另外,可以使用在其部分结构具有TPD等联苯胺衍生物的结构的高分子化合物等。
作为本发明的有机EL元件的电子阻挡层,可以使用4,4’,4”-三(N-咔唑基)三苯基胺(TCTA)、9,9-双[4-(咔唑-9-基)苯基]芴、1,3-双(咔唑-9-基)苯(mCP)、2,2-双(4-咔唑-9-基-苯基)金刚烷(Ad-Cz)等咔唑衍生物、9-[4-(咔唑-9-基)苯基]-9-[4-(三苯基甲硅烷基)苯基]-9H-芴所代表的具有三苯基甲硅烷基和三芳基胺结构的化合物等具有电子阻挡作用的化合物。它们可以单独成膜,也可以以与其它材料混合成膜而得到的单层的形式加以使用,还可以制成单独成膜的层彼此的层叠结构、混合成膜的层彼此的层叠结构、或者单独成膜的层与混合成膜的层的层叠结构。这些材料除了蒸镀法之外,也可以利用旋涂法、喷墨法等公知方法来进行薄膜形成。
作为本发明的有机EL元件的发光层,除了以Alq3为首的羟基喹啉衍生物的金属络合物之外,还可以使用各种金属络合物、蒽衍生物、双苯乙烯基苯衍生物、芘衍生物、噁唑衍生物、聚对亚苯基亚乙烯基衍生物等。另外,发光层可以由主体材料和掺杂材料构成,作为主体材料,优选使用蒽衍生物,另外,可以在使用前述发光材料的基础上,还使用具有吲哚环作为稠环的部分结构的杂环化合物、具有咔唑环作为稠环的部分结构的杂环化合物、咔唑衍生物、噻唑衍生物、苯并咪唑衍生物、聚二烷基芴衍生物等。另外,作为掺杂材料,可以使用喹吖啶酮、香豆素、红荧烯、苝和它们的衍生物、苯并吡喃衍生物、罗丹明衍生物、氨基苯乙烯基衍生物等,更优选使用绿色发光材料。它们可以单独成膜,也可以以与其它材料混合成膜而得到的单层的形式加以使用,还可以制成单独成膜的层彼此的层叠结构、混合成膜的层彼此的层叠结构、或者单独成膜的层与混合成膜的层的层叠结构。
另外,作为发光材料,也可以使用磷光发光体。作为磷光发光体,可以使用铱、铂等金属络合物的磷光发光体。可以使用Ir(ppy)3等绿色的磷光发光体、FIrpic、FIr6等蓝色的磷光发光体、Btp2Ir(acac)等红色的磷光发光体等,更优选使用绿色的磷光发光体。关于此时的主体材料,作为空穴注入/输送性的主体材料,可以使用4,4’-二(N-咔唑基)联苯(CBP)、TCTA、mCP等咔唑衍生物。作为电子输送性的主体材料,可以使用对双(三苯基甲硅烷基)苯(UGH2)、2,2’,2”-(1,3,5-亚苯基)-三(1-苯基-1H-苯并咪唑)(TPBI)等,能够制作高性能的有机EL元件。
关于磷光性的发光材料在主体材料中的掺杂,为了避免浓度淬灭,优选以相对于发光层整体为1~30重量%的范围通过共蒸镀来进行掺杂。
另外,作为发光材料,也可以使用放射延迟荧光的材料。这些材料除了蒸镀法之外,也可以利用旋涂法、喷墨法等公知方法来进行薄膜形成。
作为本发明的有机EL元件的空穴阻挡层,可以使用浴铜灵(BCP)等菲绕啉衍生物、铝(III)双(2-甲基-8-羟基喹啉)-4-苯基苯酚盐(BAlq)等羟基喹啉衍生物的金属络合物、各种稀土络合物、三唑衍生物、三嗪衍生物、嘧啶衍生物、噁二唑衍生物、苯并唑衍生物等具有空穴阻挡作用的化合物。这些材料可以兼作电子输送层的材料。它们可以单独成膜,也可以以与其它材料混合成膜而得到的单层的形式加以使用,还可以制成单独成膜的层彼此的层叠结构、混合成膜的层彼此的层叠结构、或者单独成膜的层与混合成膜的层的层叠结构。这些材料除了蒸镀法之外,也可以利用旋涂法、喷墨法等公知方法来进行薄膜形成。
作为本发明的有机EL元件的电子输送层,除了使用以Alq3、Balq为首的羟基喹啉衍生物的金属络合物之外,还可以使用各种金属络合物、三唑衍生物、三嗪衍生物、嘧啶衍生物、噁二唑衍生物、吡啶衍生物、苯并咪唑衍生物、苯并唑衍生物、噻二唑衍生物、蒽衍生物、碳二亚胺衍生物、喹喔啉衍生物、吡啶并吲哚衍生物、菲绕啉衍生物、硅杂环戊二烯衍生物等。它们可以单独成膜,也可以以与其它材料混合成膜而得到的单层的形式加以使用,还可以制成单独成膜的层彼此的层叠结构、混合成膜的层彼此的层叠结构、或者单独成膜的层与混合成膜的层的层叠结构。这些材料除了蒸镀法之外,也可以利用旋涂法、喷墨法等公知方法来进行薄膜形成。
作为本发明的有机EL元件的电子注入层,可以使用氟化锂、氟化铯等碱金属盐;氟化镁等碱土金属盐;羟基喹啉锂等羟基喹啉衍生物的金属络合物;氧化铝等金属氧化物;或者镱(Yb)、钐(Sm)、钙(Ca)、锶(Sr)、铯(Cs)等金属等,在电子输送层和阴极的优选选择中可以将其省略。
进而,在电子注入层或电子输送层中,可以使用对于该层中通常使用的材料进一步n掺杂铯等金属而得到的物质。
作为本发明的有机EL元件的阴极,可以将铝之类的功函数低的电极材料、镁银合金、镁钙合金、镁铟合金、铝镁合金之类的功函数更低的合金、ITO、IZO等用作电极材料。
作为本发明的有机EL元件的覆盖层,优选为第一覆盖层和第二覆盖层的二层结构,在该情况下,作为与阴极电极邻接的第一覆盖层,优选使用本发明的前述通式(1)所示的金刚烷化合物。
它们可以单独成膜,也可以以与其它材料一同混合成膜而得到的单层的形式使用。这些材料除了蒸镀法之外,也可以利用旋涂法、喷墨法等公知方法来进行薄膜形成。
作为本发明的前述通式(1)所示的金刚烷化合物,波长400nm~700nm的范围内的折射率优选为1.6以下、更优选为1.5以下。
在本发明的有机EL元件中,作为层叠在第一覆盖层上的第二覆盖层,优选使用高折射率的芳基胺化合物。作为高折射率的芳基胺化合物,波长450nm~700nm的范围内的折射率优选为1.6以上、更优选为1.8以上、进一步优选为1.9以上。作为这些高折射率的芳基胺化合物,优选使用图9~图10中例示那样的、在分子中具有将2个三苯基胺结构借助单键或亚苯基进行连接而得到的结构,且具有2个苯并唑基或苯并三唑基作为取代基的化合物;或者,在分子中仅具有1个三苯基胺结构,且具有2个或3个苯并唑基、苯并三唑基或苯并噻吩基作为取代基的化合物。
这些化合物在蓝、绿和红各自的波长区域内不具有吸收,因此在想要显示色纯度良好且清晰明亮的图像时特别适合。
它们可以单独成膜,也可以以与其它材料一同混合成膜而得到的单层的形式使用。这些材料除了蒸镀法之外,也可以利用旋涂法、喷墨法等公知方法来进行薄膜形成。
构成第二覆盖层的材料的折射率优选比邻接的第一覆盖层的折射率还大出0.2以上([第二覆盖层的折射率]-[第一覆盖层的折射率]≥0.2)。即,有机EL元件中的光取出效率因第二覆盖层而提高,但其效果因第二覆盖层与第一覆盖层的界面处的反射率大时光干涉的效果大而更为有效。因此,构成第二覆盖层的材料的折射率优选比邻接的第一覆盖层的折射率还大出0.2以上。
需要说明的是,以上针对顶部发光结构的有机EL元件进行了说明,但本发明不限定于此,关于底部发光结构的有机EL元件、从上部和底部两者发光的双发光结构的有机EL元件,也可以同样地应用。在这些情况下,处于从发光元件向外部取出光的方向上的电极需要为透明或半透明。
以下,针对本发明的实施方式,通过实施例进行具体说明,但本发明只要不超出其主旨就不限定于以下的实施例。
[实施例1]
<N,N’-金刚烷-1,3-二基双(4-氟苯酰胺)(1-13)的合成>
向经氮气置换的反应容器中添加金刚烷-1,3-二胺5.0g、四氢呋喃120mL、碳酸钾10.4g,耗费10分钟滴加4-氟苯甲酰氯10.5g,进而,在25℃下搅拌4小时。添加水100mL并在减压下馏去四氢呋喃后,通过过滤来采集所析出的固体。添加甲醇60mL、水60mL,进行1小时的回流分散清洗,在冷却至室温后,通过过滤来采集固体。溶解于二氯甲烷180mL,添加硅胶6g,在25℃下搅拌1小时1小时后,通过过滤来去除硅胶。将滤液浓缩,残渣用甲醇清洗,由此得到N,N’-金刚烷-1,3-二基双(4-氟苯酰胺)(1-13)的白色粉体8.4g(收率为68%)。
针对所得白色粉体,使用NMR来鉴定结构。
利用1H-NMR(CDCl3),检测到以下的24个氢的信号。
δ(ppm)=7.71-7.74(4H)、7.06-7.11(4H)、5.31(2H)、2.57(2H)、2.33(2H)、2.07-2.19(8H)、1.71(2H)。
[实施例2]
<N,N’-金刚烷-1,3-二基双(3,5-二氟苯酰胺)(1-18)的合成>
在实施例1中,将4-氟苯甲酰氯替换成3,5-二氟苯甲酰氯,进行相同的操作,得到N,N’-金刚烷-1,3-二基双(3,5-二氟苯酰胺)(1-18)的白色粉体11.4g(收率为80.9%)。
针对所得白色粉体,使用NMR来鉴定结构。
利用1H-NMR(CDCl3),检测到以下的22个氢的信号。
δ(ppm)=7.22-7.29(4H)、6.92-6.97(2H)、5.88(2H)、2.57(2H)、2.37(2H)、2.07-2.18(8H)、1.73(2H)。
[实施例3]
<N,N’-金刚烷-1,3-二基双(五氟苯酰胺)(1-23)的合成>
在实施例1中,将4-氟苯甲酰氯替换成五氟苯甲酰氯,进行相同的操作,得到N,N’-金刚烷-1,3-二基双(五氟苯酰胺)(1-23)的白色粉体9.0g(收率为54%)。
针对所得白色粉体,使用NMR和质谱分析来鉴定结构。
利用1H-NMR(DMSO-d6),检测到以下的16个氢的信号。
δ(ppm)=8.64(2H)、2.36(2H)、2.23(2H)、1.93-2.04(8H)、1.61(2H)。
利用13C-NMR(DMSO-d6),检测到以下的13C信号。
δ(ppm)=157.0、144.6、142.5、142.2、140.0、138.5、138.4、136.2、136.0、114.1、113.9、113.6、67.5、54.1、54.0、44.4、39.4、35.1、29.6、25.6。
m/z(M+1)=555
[实施例4]
针对通式(1)所示的金刚烷化合物,利用高灵敏度差示扫描量热计(BRUKER AXS公司制、DSC3100SA)来测定玻璃化转变温度(Tg)和熔点。
[实施例5]
使用通式(1)所示的金刚烷化合物,在硅基板上制作膜厚80nm的蒸镀膜,使用分光测定装置(FILMETRICS公司制、F10-RT-UV),测定波长400nm、450nm、700nm处的折射率n。另外,为了加以对比,也针对高折射率的芳基胺化合物(2-8)和Alq3进行测定。将测定结果总结示于表1。
[表1]
像这样,本发明的通式(1)所示的金刚烷化合物的折射率在波长400nm~700nm的范围内为1.60以下,且具有比高折射率的芳基胺化合物(2-8)的折射率小0.2以上的值。
[实施例6]
有机EL元件如图11所示那样,通过在玻璃基板1上预先形成反射ITO电极来作为金属阳极2,并在由此得到的物体上依次蒸镀空穴注入层3、空穴输送层4、发光层5、电子输送层6、电子注入层7、阴极8、第一覆盖层9、第二覆盖层10来制作。
具体而言,在玻璃基板1上依次成膜出膜厚50nm的ITO、膜厚100nm的银合金的反射膜、膜厚5nm的ITO作为金属阳极2,并在异丙醇中进行20分钟的超声波清洗后,在加热至250℃的加热板上进行10分钟的干燥。其后,在进行2分钟的UV臭氧处理后,将该带有ITO的玻璃基板置于真空蒸镀机内,减压至0.001Pa以下。接着,以覆盖金属阳极2的方式,将下述结构式的电子受体(受体-1)和下述结构式的化合物(3-1)按照蒸镀速度比成为(受体-1):化合物(3-1)=3:97的蒸镀速度进行二元蒸镀,以膜厚成为10nm的方式形成空穴注入层3。在该空穴注入层3上,将下述结构式的化合物(3-1)以膜厚成为140nm的方式形成为空穴输送层4。在该空穴输送层4上,将下述结构式的化合物(EMD-1)和下述结构式的化合物(EMH-1)按照蒸镀速度比成为化合物(EMD-1):化合物(EMH-1)=5:95的蒸镀速度进行二元蒸镀,以膜厚成为20nm的方式形成为发光层5。在该发光层5上,将下述结构式的化合物(4-1)和下述结构式的化合物(ETM-1)按照蒸镀速度比成为化合物(4-1):化合物(ETM-1)=50:50的蒸镀速度进行二元蒸镀,以膜厚成为30nm的方式形成为电子输送层6。在该电子输送层6上,将氟化锂以膜厚成为1nm的方式形成为电子注入层7。在该电子注入层7上,将镁银合金以膜厚成为12nm的方式形成为阴极8。在阴极8上,将实施例1的化合物(1-13)以膜厚成为30nm的方式形成为第一覆盖层9,最后,将高折射率的芳基胺化合物(2-8)以膜厚成为30nm的方式形成为第二覆盖层10。针对所制作的有机EL元件,在大气中、常温下进行特性测定。
将对所制作的有机EL元件施加直流电压而得到的发光特性的测定结果总结示于表2。
[实施例7]
在实施例6中,作为第一覆盖层9,使用实施例2的化合物(1-18)来代替实施例1的化合物(1-13),除此之外,利用相同的条件来制作有机EL元件。针对所制作的有机EL元件,在大气中、常温下进行特性测定。
将对所制作的有机EL元件施加直流电压而得到的发光特性的测定结果总结示于表2。
[实施例8]
在实施例6中,作为第一覆盖层9,使用实施例3的化合物(1-23)来代替实施例1的化合物(1-13),除此之外,利用相同的条件来制作有机EL元件。针对所制作的有机EL元件,在大气中、常温下进行特性测定。
将对所制作的有机EL元件施加直流电压而得到的发光特性的测定结果总结示于表2。
[比较例1]
为了加以对比,在实施例6中,作为第一覆盖层9,使用Alq3来代替实施例1的化合物(1-13),除此之外,利用相同的条件来制作有机EL元件。针对所制作的有机EL元件,在大气中、常温下进行特性测定。
将对所制作的有机EL元件施加直流电压而得到的发光特性的测定结果总结示于表2。
[比较例2]
为了加以对比,在实施例6中,作为第二覆盖层10,以成为2倍膜厚60nm的方式来形成高折射率的芳基胺化合物(2-8),制作不具有第一覆盖层9的有机EL元件。针对所制作的有机EL元件,在大气中、常温下进行特性测定。
将对所制作的有机EL元件施加直流电压而得到的发光特性的测定结果总结示于表2。
使用实施例6~8和比较例1~2中制作的有机EL元件,测定元件寿命,并将结果总结示于表2。关于元件寿命,在进行10mA/cm2的恒定电流驱动时,作为将初始亮度设为100%时衰减至95%为止的时间(95%衰减)来进行测定。
[表2]
如表2所示那样,关于电流密度为10mA/cm2时的驱动电压,比较例1和比较例2的元件与使用本发明的通式(1)所示的金刚烷化合物作为第一覆盖层的实施例6~8的元件大致同等,与此相对,关于亮度、发光效率、电力效率和元件寿命,实施例6~8的元件与比较例1和比较例2的元件相比均明显提高。这表示:通过制成在包含本发明的通式(1)所示的金刚烷化合物的第一覆盖层上层叠第二覆盖层的层叠结构,进而,以第一覆盖层与第二覆盖层的折射率的差值变大的方式与第二覆盖层的材料加以组合,从而能够大幅改善光的取出效率。
产业上的可利用性
在覆盖层中包含本发明的通式(1)所示的金刚烷化合物的有机EL元件、尤其是在包含本发明的通式(1)所示的金刚烷化合物的第一覆盖层上层叠折射率之差变大那样的材料来作为第二覆盖层的有机EL元件能够得到高的光取出效率。另外,通过使用在蓝、绿和红各自的波长区域内不具有吸收的该化合物,从而在想要显示出色纯度良好且清晰明亮的图像的情况下特别适合。可以在例如家电制品、照明用途中展开应用。
附图标记说明
1玻璃基板
2金属阳极
3空穴注入层
4空穴输送层
5发光层
6电子输送层
7电子注入层
8阴极
9第一覆盖层
10第二覆盖层
Claims (11)
7.一种有机薄膜,其特征在于,其包含权利要求1~6中任一项所述的金刚烷化合物,所述有机薄膜在波长400nm~700nm的范围内的折射率为1.60以下。
8.一种有机电致发光元件,其特征在于,其至少依次具有阳极电极、空穴输送层、发光层、电子输送层、阴极电极和覆盖层,所述覆盖层为权利要求7所述的有机薄膜。
9.一种有机电致发光元件,其特征在于,其至少依次具有阳极电极、空穴输送层、发光层、电子输送层、阴极电极和覆盖层,所述覆盖层为第一覆盖层和第二覆盖层的二层结构,第一覆盖层为权利要求7所述的有机薄膜。
10.根据权利要求9所述的有机电致发光元件,其特征在于,所述第一覆盖层的折射率与第二覆盖层的折射率之差([第二覆盖层的折射率]-[第一覆盖层的折射率])为0.2以上。
11.一种电子设备或电子元件,其特征在于,其具有一对电极和夹在其间的至少一层有机层,所述有机层使用权利要求1~6中任一项所述的金刚烷化合物作为其构成材料。
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