JPWO2012070535A1 - Electron transport material and organic electroluminescent device using the same - Google Patents
Electron transport material and organic electroluminescent device using the same Download PDFInfo
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- JPWO2012070535A1 JPWO2012070535A1 JP2012545745A JP2012545745A JPWO2012070535A1 JP WO2012070535 A1 JPWO2012070535 A1 JP WO2012070535A1 JP 2012545745 A JP2012545745 A JP 2012545745A JP 2012545745 A JP2012545745 A JP 2012545745A JP WO2012070535 A1 JPWO2012070535 A1 JP WO2012070535A1
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- carbon atoms
- compound
- alkyl
- cycloalkyl
- organic
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- 239000000463 material Substances 0.000 title claims abstract description 51
- 150000001875 compounds Chemical class 0.000 claims abstract description 138
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 238000002347 injection Methods 0.000 claims abstract description 25
- 239000007924 injection Substances 0.000 claims abstract description 25
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 11
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 6
- 150000002910 rare earth metals Chemical class 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 4
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 3
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 2
- 150000008045 alkali metal halides Chemical class 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 239000011368 organic material Substances 0.000 claims description 2
- 229910001404 rare earth metal oxide Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims 1
- 239000010409 thin film Substances 0.000 abstract description 9
- 125000001624 naphthyl group Chemical group 0.000 abstract description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 132
- 239000010410 layer Substances 0.000 description 76
- 238000006243 chemical reaction Methods 0.000 description 56
- 230000015572 biosynthetic process Effects 0.000 description 51
- 238000003786 synthesis reaction Methods 0.000 description 50
- 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 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
- 238000012360 testing method Methods 0.000 description 32
- 238000000034 method Methods 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 30
- 238000007740 vapor deposition Methods 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- -1 2,2′-bipyridyl compound Chemical class 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 26
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- 238000000151 deposition Methods 0.000 description 18
- 230000008021 deposition Effects 0.000 description 17
- 239000010408 film Substances 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- 229910001316 Ag alloy Inorganic materials 0.000 description 15
- 0 CC(C)(C(C)(C)O*c(cc1)ccc1-c1c(cccc2)c2c(-c2cccc3ccccc23)c2c1cccc2)O Chemical compound CC(C)(C(C)(C)O*c(cc1)ccc1-c1c(cccc2)c2c(-c2cccc3ccccc23)c2c1cccc2)O 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 15
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 15
- 229910052750 molybdenum Inorganic materials 0.000 description 15
- 239000011733 molybdenum Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 13
- 229910052749 magnesium Inorganic materials 0.000 description 13
- 239000011777 magnesium Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 229910000160 potassium phosphate Inorganic materials 0.000 description 12
- 235000011009 potassium phosphates Nutrition 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- XERBRCOTJFZZHS-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[4-(10-naphthalen-1-ylanthracen-9-yl)phenyl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C3=CC=CC=C3C(C=3C4=CC=CC=C4C=CC=3)=C3C=CC=CC3=2)C=C1 XERBRCOTJFZZHS-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- YPNZWHZIYLWEDR-UHFFFAOYSA-N 9-naphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=C(C=CC=C3)C3=CC2=C1 YPNZWHZIYLWEDR-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 7
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 6
- SYACRXBYRNYMLN-UHFFFAOYSA-N 9-bromo-10-naphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 SYACRXBYRNYMLN-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 239000012043 crude product Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- ASQXKNXJNDLXQV-UHFFFAOYSA-N (10-naphthalen-1-ylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 ASQXKNXJNDLXQV-UHFFFAOYSA-N 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- GYJBDJGUNDKZKO-UHFFFAOYSA-N 4-(4-bromophenyl)pyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=NC=C1 GYJBDJGUNDKZKO-UHFFFAOYSA-N 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 4
- 150000001649 bromium compounds Chemical group 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 125000001979 organolithium group Chemical group 0.000 description 4
- 125000002734 organomagnesium group Chemical group 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 3
- YRRWZYUKADXREU-UHFFFAOYSA-N 3-methyl-5-[3-(10-naphthalen-1-ylanthracen-9-yl)phenyl]pyridine Chemical compound CC1=CN=CC(C=2C=C(C=CC=2)C=2C3=CC=CC=C3C(C=3C4=CC=CC=C4C=CC=3)=C3C=CC=CC3=2)=C1 YRRWZYUKADXREU-UHFFFAOYSA-N 0.000 description 3
- NACRJIMZNKRXNO-UHFFFAOYSA-N 3-methyl-5-[4-(10-naphthalen-1-ylanthracen-9-yl)phenyl]pyridine Chemical compound CC1=CN=CC(C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C4=CC=CC=C4C=CC=3)=C3C=CC=CC3=2)=C1 NACRJIMZNKRXNO-UHFFFAOYSA-N 0.000 description 3
- WFCZNBYHFXUMDE-UHFFFAOYSA-N 4-(10-naphthalen-1-ylanthracen-9-yl)phenol Chemical compound C1=CC(O)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 WFCZNBYHFXUMDE-UHFFFAOYSA-N 0.000 description 3
- AVLCPEDEFXQCDF-UHFFFAOYSA-N 4-[3-(10-naphthalen-1-ylanthracen-9-yl)phenyl]pyridine Chemical compound C=1C=CC2=CC=CC=C2C=1C(C1=CC=CC=C11)=C2C=CC=CC2=C1C(C=1)=CC=CC=1C1=CC=NC=C1 AVLCPEDEFXQCDF-UHFFFAOYSA-N 0.000 description 3
- RTLUPHDWSUGAOS-UHFFFAOYSA-N 4-iodopyridine Chemical compound IC1=CC=NC=C1 RTLUPHDWSUGAOS-UHFFFAOYSA-N 0.000 description 3
- YSZYPHXDKVQWHS-UHFFFAOYSA-N 9-(4-methoxyphenyl)-10-naphthalen-1-ylanthracene Chemical compound C1=CC(OC)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 YSZYPHXDKVQWHS-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- 238000006411 Negishi coupling reaction Methods 0.000 description 3
- 101150003085 Pdcl gene Proteins 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
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- 125000005577 anthracene group Chemical group 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 3
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 3
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CTPUUDQIXKUAMO-UHFFFAOYSA-N 1-bromo-3-iodobenzene Chemical compound BrC1=CC=CC(I)=C1 CTPUUDQIXKUAMO-UHFFFAOYSA-N 0.000 description 2
- CCZWSTFVHJPCEM-UHFFFAOYSA-N 2-iodopyridine Chemical compound IC1=CC=CC=N1 CCZWSTFVHJPCEM-UHFFFAOYSA-N 0.000 description 2
- BQWSPEHKSNVVTQ-UHFFFAOYSA-N 2-methyl-4-[4-(10-naphthalen-1-ylanthracen-9-yl)phenyl]pyridine Chemical compound C1=NC(C)=CC(C=2C=CC(=CC=2)C=2C3=CC=CC=C3C(C=3C4=CC=CC=C4C=CC=3)=C3C=CC=CC3=2)=C1 BQWSPEHKSNVVTQ-UHFFFAOYSA-N 0.000 description 2
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- FUWBQRWFFHNZFC-UHFFFAOYSA-N N1=C(C=CC=C1)C1=CC=C(C2=CC=CC=C12)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=C(C2=CC=CC=C12)C1=NC=CC=C1 Chemical compound N1=C(C=CC=C1)C1=CC=C(C2=CC=CC=C12)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=C(C2=CC=CC=C12)C1=NC=CC=C1 FUWBQRWFFHNZFC-UHFFFAOYSA-N 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical class C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004768 bromobenzenes Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- VHRBNZMKWWSWCN-UHFFFAOYSA-N c(cc1)ccc1-c(c1c2cccc1)ccc2-c1c(cccc2)c2c(-c(cc2)ccc2-c2ccnc(-c3cc(cccc4)c4cc3)c2)c2c1cccc2 Chemical compound c(cc1)ccc1-c(c1c2cccc1)ccc2-c1c(cccc2)c2c(-c(cc2)ccc2-c2ccnc(-c3cc(cccc4)c4cc3)c2)c2c1cccc2 VHRBNZMKWWSWCN-UHFFFAOYSA-N 0.000 description 1
- MHWXQOLMLLUPDO-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)c(cccc2)c2c1-c1c(cccc2)c2c(-c2cc(-c3cc(-c4ccc(cccc5)c5c4)ncc3)ccc2)c2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)c(cccc2)c2c1-c1c(cccc2)c2c(-c2cc(-c3cc(-c4ccc(cccc5)c5c4)ncc3)ccc2)c2c1cccc2 MHWXQOLMLLUPDO-UHFFFAOYSA-N 0.000 description 1
- RNPUECIDZVGTPW-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)c(cccc2)c2c1-c1c(cccc2)c2c(-c2cccc(-c3ccc(-c4ccccc4)nc3)c2)c2c1cccc2 Chemical compound c(cc1)ccc1-c(cc1)c(cccc2)c2c1-c1c(cccc2)c2c(-c2cccc(-c3ccc(-c4ccccc4)nc3)c2)c2c1cccc2 RNPUECIDZVGTPW-UHFFFAOYSA-N 0.000 description 1
- QRTPJLZIXPTBGH-UHFFFAOYSA-N c(cc1)ccc1-c1cccc2c1cccc2-c1c(cccc2)c2c(-c2cc(-c3cc(-c4ccc(cccc5)c5c4)ncc3)ccc2)c2c1cccc2 Chemical compound c(cc1)ccc1-c1cccc2c1cccc2-c1c(cccc2)c2c(-c2cc(-c3cc(-c4ccc(cccc5)c5c4)ncc3)ccc2)c2c1cccc2 QRTPJLZIXPTBGH-UHFFFAOYSA-N 0.000 description 1
- IEAFVHQZVZRXOG-UHFFFAOYSA-N c(cc1)ccc1-c1cccc2c1cccc2-c1c(cccc2)c2c(-c2cccc(-c3ccc(-c4ccccc4)nc3)c2)c2c1cccc2 Chemical compound c(cc1)ccc1-c1cccc2c1cccc2-c1c(cccc2)c2c(-c2cccc(-c3ccc(-c4ccccc4)nc3)c2)c2c1cccc2 IEAFVHQZVZRXOG-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 150000001882 coronenes Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- IYALFASAICOWQU-UHFFFAOYSA-L dichlorozinc;pyridine Chemical compound [Cl-].[Cl-].[Zn+2].C1=CC=NC=C1 IYALFASAICOWQU-UHFFFAOYSA-L 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- NNNFHIWKVLLMKH-UHFFFAOYSA-N ditert-butyl-[1-(2-ditert-butylphosphanylnaphthalen-1-yl)naphthalen-2-yl]phosphane Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3P(C(C)(C)C)C(C)(C)C)=C(P(C(C)(C)C)C(C)(C)C)C=CC2=C1 NNNFHIWKVLLMKH-UHFFFAOYSA-N 0.000 description 1
- MUPGNOONALUUNP-UHFFFAOYSA-N ditert-butyl-[1-(2-methoxynaphthalen-1-yl)naphthalen-2-yl]phosphane Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3OC)=C(P(C(C)(C)C)C(C)(C)C)C=CC2=C1 MUPGNOONALUUNP-UHFFFAOYSA-N 0.000 description 1
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000005678 ethenylene group Chemical class [H]C([*:1])=C([H])[*:2] 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 150000002258 gallium Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 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
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- IUYHWZFSGMZEOG-UHFFFAOYSA-M isopropylmagnesium chloride Substances [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- GRJHONXDTNBDTC-UHFFFAOYSA-N phenyl trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1 GRJHONXDTNBDTC-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000123 polythiophene Chemical class 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000004322 quinolinols Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical class 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
- 150000003839 salts Chemical class 0.000 description 1
- 150000003967 siloles Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 150000003518 tetracenes Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 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 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
Abstract
本発明の式(1)で表される化合物は薄膜状態で電圧を印加しても安定で、電荷の輸送能力が高いという特徴を持つ。本発明の化合物は有機EL素子における電荷輸送材料として適しており、この電子輸送材料を有機EL素子の電子輸送層および/または電子注入層に用いることで、長い寿命を有する有機EL素子を得ることができる。式(1)において、Pyはピリジルであり、このピリジルの任意の水素はアルキル、シクロアルキル、フェニル、1−ナフチル、または2−ナフチルで置き換えられていてもよく、フェニル、1−ナフチルおよび2−ナフチルはさらにアルキルまたはシクロアルキルで置換されていてもよく;Rは水素、アルキル、シクロアルキルまたはアリールであり、このアリールの任意の水素はアルキルまたはシクロアルキルで置き換えられていてもよい。The compound represented by the formula (1) of the present invention is characterized by being stable even when a voltage is applied in a thin film state and having a high charge transport capability. The compound of the present invention is suitable as a charge transport material in an organic EL device. By using this electron transport material for an electron transport layer and / or an electron injection layer of an organic EL device, an organic EL device having a long lifetime can be obtained. Can do. In formula (1), Py is pyridyl and any hydrogen of the pyridyl may be replaced by alkyl, cycloalkyl, phenyl, 1-naphthyl, or 2-naphthyl, phenyl, 1-naphthyl and 2-naphthyl. Naphthyl may be further substituted with alkyl or cycloalkyl; R is hydrogen, alkyl, cycloalkyl or aryl, and any hydrogen of the aryl may be replaced with alkyl or cycloalkyl.
Description
本発明は、ピリジル基を有する新規な電子輸送材料、この電子輸送材料を用いた有機電界発光素子(以下、有機EL素子または単に素子と略記することがある。)等に関する。 The present invention relates to a novel electron transport material having a pyridyl group, an organic electroluminescence device using the electron transport material (hereinafter, sometimes abbreviated as an organic EL device or simply a device), and the like.
近年、次世代のフルカラーフラットパネルディスプレイとして有機EL素子が注目され、活発な研究がなされている。有機EL素子の実用化を促進するには、素子の駆動電圧の低減、長寿命化が不可欠な要素であり、これらを達成するために新しい電子輸送材料の開発がなされてきた。特に、青色素子の駆動電圧低下、長寿命化は必須である。特許文献1(特開2003−123983号公報)には、フェナントロリン誘導体またはその類似体である2,2’−ビピリジル化合物を電子輸送材料に使用することで有機EL素子を低電圧で駆動させることができると記載されている。しかしながらこの文献の実施例に報告されている素子の特性(駆動電圧、発光効率など)は比較例を基準にした相対値のみであり、実用的な値と判断できる実測値は記載されていない。他に、2,2’−ビピリジル化合物を電子輸送材料に使用した例が、非特許文献1(Proceedings of the 10th International Workshop on Inorganic and Organic Electroluminescence)、特許文献2(特開2002−158093号公報)および特許文献3(国際公開2007/86552パンフレット)に開示されている。非特許文献1に記載されている化合物はTgが低く、実用的ではなかった。特許文献2および3に記載の化合物は比較的低電圧で有機EL素子を駆動させることができるが、実用化に向けてはより長寿命化が望まれている。In recent years, organic EL elements have attracted attention as next-generation full-color flat panel displays, and active research has been conducted. In order to promote the practical use of organic EL elements, it is indispensable to reduce the drive voltage and extend the life of the elements, and new electron transport materials have been developed to achieve these. In particular, it is essential to lower the driving voltage and extend the life of the blue element. Patent Document 1 (Japanese Patent Laid-Open No. 2003-123983) discloses that an organic EL device can be driven at a low voltage by using a 2,2′-bipyridyl compound that is a phenanthroline derivative or an analog thereof as an electron transport material. It is stated that it can be done. However, the element characteristics (driving voltage, light emission efficiency, etc.) reported in the examples of this document are only relative values based on comparative examples, and no actual measurement values that can be judged as practical values are described. Alternatively, example of using 2,2'-bipyridyl compound to the electron transport material, non-patent document 1 (Proceedings of the 10 th International Workshop on Inorganic and Organic Electroluminescence), Patent Document 2 (JP 2002-158093 JP ) And Patent Document 3 (International Publication No. 2007/86552 pamphlet). The compound described in Non-Patent Document 1 has a low Tg and is not practical. Although the compounds described in Patent Documents 2 and 3 can drive an organic EL device at a relatively low voltage, longer life is desired for practical use.
本発明は、このような従来技術が有する課題に鑑みてなされたものである。本発明は、有機EL素子の長寿命化等に寄与する電子輸送材料を提供することを課題とする。さらに本発明は、この電子輸送材料を用いた有機EL素子を提供することを課題とする。 The present invention has been made in view of the problems of such conventional techniques. It is an object of the present invention to provide an electron transport material that contributes to extending the lifetime of an organic EL element. Furthermore, this invention makes it a subject to provide the organic EL element using this electron transport material.
本発明者らは鋭意検討した結果、9−(1−ナフチル)−10−フェニルアントラセンのフェニルにピリジルを有した化合物を有機EL素子の電子輸送層に用いることにより、長寿命で駆動できる有機EL素子が得られることを見出し、この知見に基づいて本発明を完成した。
上記の課題は以下に示す各項によって解決される。As a result of intensive studies, the present inventors have found that organic EL that can be driven with a long lifetime by using a compound of 9- (1-naphthyl) -10-phenylanthracene having a pyridyl in the electron transport layer of an organic EL device. It was found that an element was obtained, and the present invention was completed based on this finding.
Said subject is solved by each item shown below.
[1] 下記式(1)で表される化合物。
Pyはピリジルであり、このピリジルの任意の水素は炭素数1〜6のアルキル、炭素数3〜6のシクロアルキル、炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよいフェニル、炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよい1−ナフチル、または炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよい2−ナフチルで置き換えられていてもよく;
Rは水素、炭素数1〜6のアルキル、炭素数3〜6のシクロアルキルまたは炭素数6〜14のアリールであり、このアリールの任意の水素は炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置き換えられていてもよく;また、
式(1)で表される化合物における少なくとも1つの水素が重水素で置き換えられていてもよい。[1] A compound represented by the following formula (1).
Py is pyridyl, and any hydrogen of the pyridyl is substituted with alkyl having 1 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 6 carbons. 1-naphthyl optionally substituted with phenyl, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, or alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms Optionally substituted with 2-naphthyl;
R is hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 14 carbon atoms, and any hydrogen in the aryl is alkyl having 1 to 6 carbon atoms or 3 to 3 carbon atoms. Optionally substituted with 6 cycloalkyl;
At least one hydrogen in the compound represented by the formula (1) may be replaced with deuterium.
[2] 下記式(1−1)または(1−2)で表される、前記[1]項に記載の化合物。
Pyはピリジルであり、このピリジルの任意の水素は炭素数1〜6のアルキル、炭素数3〜6のシクロアルキル、炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよいフェニル、炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよい1−ナフチル、または炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよい2−ナフチルで置き換えられていてもよく;
Rは水素、炭素数1〜6のアルキル、炭素数3〜6のシクロアルキルまたは炭素数6〜14のアリールであり、このアリールの任意の水素は炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置き換えられていてもよく;また、
式(1−1)または(1−2)で表される化合物における少なくとも1つの水素が重水素で置き換えられていてもよい。[2] The compound according to [1], which is represented by the following formula (1-1) or (1-2).
Py is pyridyl, and any hydrogen of the pyridyl is substituted with alkyl having 1 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 6 carbons. 1-naphthyl optionally substituted with phenyl, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, or alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms Optionally substituted with 2-naphthyl;
R is hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 14 carbon atoms, and any hydrogen in the aryl is alkyl having 1 to 6 carbon atoms or 3 to 3 carbon atoms. Optionally substituted with 6 cycloalkyl;
At least one hydrogen in the compound represented by formula (1-1) or (1-2) may be replaced with deuterium.
[3] Pyが2−ピリジルである、前記[1]項または[2]項に記載の化合物。 [3] The compound according to [1] or [2], wherein Py is 2-pyridyl.
[4] Pyが3−ピリジルである、前記[1]項または[2]項に記載の化合物。 [4] The compound according to [1] or [2], wherein Py is 3-pyridyl.
[5] Pyが4−ピリジルである、前記[1]項または[2]項に記載の化合物。 [5] The compound according to [1] or [2], wherein Py is 4-pyridyl.
[6] Pyが下記の1価の基の群から選ばれる1つである、前記[1]項または[2]項に記載の化合物。
[7] 下記式(1−1−1)、(1−1−2)、(1−1−3)、(1−1−134)、(1−1−153)、(1−1−172)、(1−1−191)、(1−1−210)、(1−1−229)、(1−2−1)、(1−2−153)、および(1−2−172)で表される化合物の群から選ばれる1つである、前記[1]項または[2]項に記載の化合物。
[8] 前記[1]〜[7]項のいずれか1項に記載の化合物を含有する電子輸送材料。 [8] An electron transport material containing the compound according to any one of [1] to [7].
[9] 陽極および陰極からなる一対の電極と、該一対の電極間に配置される発光層と、前記陰極と該発光層との間に配置され、前記[8]項に記載の電子輸送材料を含有する電子輸送層および/または電子注入層とを有する有機電界発光素子。 [9] A pair of electrodes composed of an anode and a cathode, a light emitting layer disposed between the pair of electrodes, an electron transport material according to the item [8], disposed between the cathode and the light emitting layer. An organic electroluminescent device having an electron transport layer and / or an electron injection layer containing
[10] 前記電子輸送層および電子注入層の少なくとも1つは、さらに、キノリノール系金属錯体、ビピリジン誘導体、フェナントロリン誘導体およびボラン誘導体からなる群から選択される少なくとも1つを含有する、前記[9]項に記載の有機電界発光素子。 [10] At least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of a quinolinol-based metal complex, a bipyridine derivative, a phenanthroline derivative, and a borane derivative, [9] The organic electroluminescent element according to item.
[11] 電子輸送層および電子注入層の少なくとも1つが、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、前記[10]項に記載の有機電界発光素子。 [11] At least one of the electron transport layer and the electron injection layer further includes an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, or an alkaline earth. Containing at least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes The organic electroluminescent device as described in the item [10].
本発明の化合物は薄膜状態で電圧を印加しても安定であり、また、電荷の輸送能力が高いという特徴を持つ。本発明の化合物は有機EL素子における電荷輸送材料として適している。本発明の化合物を有機EL素子の電子輸送層および/または電子注入層に用いることで、長い寿命を有する有機EL素子を得ることができる。本発明の有機EL素子を用いることにより、フルカラー表示等の高性能のディスプレイ装置を作成できる。 The compound of the present invention is stable even when a voltage is applied in a thin film state and has a feature of high charge transport capability. The compound of the present invention is suitable as a charge transport material in an organic EL device. By using the compound of the present invention for an electron transport layer and / or an electron injection layer of an organic EL device, an organic EL device having a long lifetime can be obtained. By using the organic EL element of the present invention, a high-performance display device such as full-color display can be created.
以下、本発明をさらに詳細に説明する。なお、本明細書においては、例えば「式(1−1−1)で表される化合物」のことを「化合物(1−1−1)」と称することがある。その他の式記号、式番号についても同様に扱われる。 Hereinafter, the present invention will be described in more detail. In the present specification, for example, the “compound represented by the formula (1-1-1)” may be referred to as “compound (1-1-1)”. Other formula symbols and formula numbers are handled in the same manner.
化合物の定義において用いる用語「任意の」は「位置だけでなく数においても自由に選択できること」を意味する場合がある。例えば、「フェニルの任意の水素は炭素数1〜6のアルキルで置き換えられていてもよい」という表現は、「1つの水素がアルキルで置き換えられてもよい」のみならず、「複数の水素が同一のアルキル、または各々異なるアルキルで置き換えられていてもよい」ことをも意味する。
本明細書の構造式、化学反応式等で用いられる記号Me、Et、i−Pr、およびt−Buは、それぞれメチル、エチル、イソプロピルおよびターシャリーブチルを表す。The term “arbitrary” used in the definition of a compound may mean “can be freely selected not only by position but also by number”. For example, the expression “any hydrogen of phenyl may be substituted with alkyl having 1 to 6 carbon atoms” is not limited to “a single hydrogen may be substituted with alkyl”, It may also mean “same alkyl, or each may be replaced by a different alkyl”.
The symbols Me, Et, i-Pr, and t-Bu used in the structural formulas, chemical reaction formulas, and the like of this specification represent methyl, ethyl, isopropyl, and tertiary butyl, respectively.
<化合物の説明>
本願の第1の発明は下記の式(1)で表される、ピリジルを有する化合物である。
1st invention of this application is a compound which has a pyridyl represented by following formula (1).
式(1)において、ピリジルが連結するフェニルの位置は任意でよいが、4位および3位が好ましい。すなわち、式(1)の化合物の好ましい態様は、下記の式(1−1)または(1−2)で表すことができる。
式(1)中のピリジルに置換する炭素数1〜6のアルキルの例はメチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、t−ブチル、n−ペンチル、イソペンチル、2,2−ジメチルプロピル、n−ヘキシル、およびイソヘキシルである。この中で好ましいアルキルはメチル、エチル、イソプロピル、およびt−ブチルであり、メチルおよびt−ブチルがより好ましい。炭素数3〜6のシクロアルキルの例はシクロプロピル、シクロブチル、シクロペンチル、シクロヘキシルである。この中で好ましいシクロアルキルは原料の入手、合成の容易さを考慮するとシクロヘキシルである。上記の例示は、ピリジルに置換するフェニル、1−ナフチル、2−ナフチルの置換基、およびRが炭素数6〜14のアリールである場合の該アリールの置換基についても同様である。 Examples of the alkyl having 1 to 6 carbon atoms substituted with pyridyl in formula (1) are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, 2,2- Dimethylpropyl, n-hexyl, and isohexyl. Of these, preferred alkyls are methyl, ethyl, isopropyl, and t-butyl, with methyl and t-butyl being more preferred. Examples of cycloalkyl having 3 to 6 carbon atoms are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Among these, a preferred cycloalkyl is cyclohexyl in consideration of availability of raw materials and ease of synthesis. The above examples are the same for the phenyl, 1-naphthyl and 2-naphthyl substituents substituted on pyridyl, and the aryl substituents when R is aryl having 6 to 14 carbon atoms.
ピリジルの置換基の位置および個数については特に限定されることはない。特にメチルについてはピリジルのどの位置に置換していてもよく、置換する数も1個から置換可能な最大の4個まで選ぶことができる。エチルよりも長いアルキル、シクロアルキル、フェニル、1−ナフチル、および2−ナフチルについては、原料の入手し易さや合成の容易さを考慮すると、ピリジルのNの隣の炭素に置換することが好ましく、そして、置換する数も1〜2個が好ましく、1個がより好ましい。 The position and number of the pyridyl substituents are not particularly limited. In particular, methyl may be substituted at any position of pyridyl, and the number of substitutions can be selected from 1 to the maximum 4 that can be substituted. For alkyl, cycloalkyl, phenyl, 1-naphthyl, and 2-naphthyl longer than ethyl, it is preferable to substitute carbon adjacent to N of pyridyl in consideration of availability of raw materials and ease of synthesis. And the number to substitute is also 1-2, and 1 is more preferable.
式(1)、(1−1)および(1−2)中の1−ナフチルに置換するRの位置は任意でよいが、原料の入手し易さを考慮すると4位および5位が好ましく、4位がより好ましい。 The position of R substituted with 1-naphthyl in the formulas (1), (1-1) and (1-2) may be arbitrary, but the 4th and 5th positions are preferable in consideration of the availability of raw materials, The 4th position is more preferable.
Rにおける炭素数1〜6のアルキルおよび炭素数3〜6のシクロアルキルの例は、前記ピリジルの置換基で例示した基が挙げられる。好ましいアルキルはメチル、エチル、イソプロピル、およびt−ブチルであり、メチルおよびt−ブチルがより好ましい。好ましいシクロアルキルは原料の入手、合成の容易さを考慮するとシクロヘキシルである。Rにおける炭素数6〜14のアリールは具体的にはフェニル、ビフェニリル、ナフチル、フェナントリルである。これらの基が置換基を有する場合の置換基の数の最大値は化学的に可能な数であるが、原料の入手、合成の容易さを考慮すると1〜3個が好ましい。好ましいRは下記の1価の基である。
上記の基の中では下記に示す基がより好ましい。
<化合物の具体例>
本発明の化合物の具体例は以下に列記する式によって示されるが、本発明はこれらの具体的な構造の開示によって限定されることはない。<Specific examples of compounds>
Specific examples of the compounds of the present invention are shown by the formulas listed below, but the present invention is not limited by the disclosure of these specific structures.
<式(1−1)で表される化合物の具体例>
式(1−1)で表される化合物の具体例は下記の式(1−1−1)〜(1−1−475)で示される。これらの中で好ましい化合物は式(1−1−1)〜(1−1−57)、(1−1−58)、(1−1−77)、(1−1−96)、(1−1−115)、(1−1−134)、(1−1−153)、(1−1−172)、(1−1−191)、(1−1−210)、および(1−1−229)であり、より好ましい化合物は式(1−1−1)〜(1−1−3)、(1−1−58)、(1−1−77)、(1−1−96)、(1−1−115)、(1−1−134)、(1−1−153)、(1−1−172)、(1−1−191)、(1−1−210)、および(1−1−229)である。<Specific Example of Compound Represented by Formula (1-1)>
Specific examples of the compound represented by the formula (1-1) are represented by the following formulas (1-1-1) to (1-1-475). Among these, preferred compounds are those represented by the formulas (1-1-1) to (1-1-57), (1-1-58), (1-1-77), (1-1-96), (1 1-115), (1-1-134), (1-1-153), (1-1-172), (1-1-191), (1-1-210), and (1- 1-229), and more preferable compounds are the formulas (1-1-1) to (1-1-3), (1-1-58), (1-1-77), (1-1-96). ), (1-1-115), (1-1-134), (1-1-153), (1-1-172), (1-1-191), (1-1-210), And (1-1-229).
<式(1−2)で表される化合物の具体例>
式(1−2)で表される化合物の具体例は下記の式(1−2−1)〜(1−2−475)で示される。これらの中で好ましい化合物は式(1−2−1)〜(1−2−57)、(1−2−58)、(1−2−77)、(1−2−96)、(1−2−115)、(1−2−134)、(1−2−153)、(1−2−172)、(1−2−191)、(1−2−210)、および(1−2−229)であり、より好ましい化合物は式(1−2−1)〜(1−2−3)、(1−2−58)、(1−2−77)、(1−2−96)、(1−2−115)、(1−2−134)、(1−2−153)、(1−2−172)、(1−2−191)、(1−2−210)、および(1−2−229)である。<Specific Example of Compound Represented by Formula (1-2)>
Specific examples of the compound represented by Formula (1-2) are shown by the following Formulas (1-2-1) to (1-2-475). Among these, preferred compounds are those represented by formulas (1-2-1) to (1-257), (1-2-58), (1-277), (1-296), (1 -2-115), (1-2134), (1-2153), (1-2172), (1-2191), (1-2210), and (1- 2-229), and more preferable compounds are the formulas (1-2-1) to (1-2-3), (1-2-58), (1-277), (1-296). ), (1-2115), (1-2134), (1-2153), (1-2172), (1-2191), (1-2210), And (1-229).
<化合物の合成法>
以下に本発明の化合物の合成法について説明する。本発明の化合物は、汎用される既知の合成法を適宜組み合わせて利用することにより合成することができる。化合物(1−1−1)を例に本発明の化合物の合成法を説明する。<Method of synthesizing compounds>
The synthesis method of the compound of the present invention will be described below. The compound of the present invention can be synthesized by appropriately combining known synthesis methods that are widely used. The method for synthesizing the compound of the present invention will be described using the compound (1-1-1) as an example.
まず、9−(ナフタレン−1−イル)アントラセンの合成法を説明する。
また、ナフタレンをボロン酸にしてカップリング反応に供する上記の工程とは逆に、アントラセンをボロン酸にしてカップリング反応させる方法も用いることができる。
続いて、9−(ナフタレン−1−イル)アントラセンの10位をボロン酸にする工程を説明する。
次に、アントラセンに連結するピリジルフェニルブロミドの合成法を説明する。
最後にアントラセンボロン酸とピリジルフェニルブロミドのカップリング反応を説明する。
上記の反応において用いる材料を適宜変更することによって、本発明の他の化合物を合成することができる。例えば、反応1や反応6で1−ブロモナフタレンの代わりに1−ブロモ−4−メチルナフタレンのようなアルキル置換したブロモベンゼンを用いることによって、アルキル置換したナフチルを有する化合物を合成することができる。 Other compounds of the present invention can be synthesized by appropriately changing the materials used in the above reaction. For example, by using alkyl-substituted bromobenzene such as 1-bromo-4-methylnaphthalene instead of 1-bromonaphthalene in Reaction 1 or Reaction 6, a compound having an alkyl-substituted naphthyl can be synthesized.
反応10で用いた4−ヨードピリジンの代わりに2−ヨードピリジンまたは3−ヨードピリジンを用いることによって、フェニルに2−ピリジルまたは3−ピリジルが置換した化合物を合成することができる。また、ヨードピリジンの代わりにブロモピリジンを用いることもできる。反応11で用いたp−ブロモヨードベンゼンの代わりにm−ブロモヨードベンゼンを用いることで、フェニルの3位にピリジルが結合した化合物を合成することができる。 By using 2-iodopyridine or 3-iodopyridine instead of 4-iodopyridine used in Reaction 10, a compound in which 2-pyridyl or 3-pyridyl is substituted on phenyl can be synthesized. Also, bromopyridine can be used in place of iodopyridine. By using m-bromoiodobenzene instead of p-bromoiodobenzene used in Reaction 11, a compound in which pyridyl is bonded to the 3-position of phenyl can be synthesized.
フェニルブロモピリジンをp−ブロモヨードベンゼンまたはm−ブロモヨードベンゼンとカップリングする工程では、上記の根岸カップリング反応に限らず、入手できる原料、試薬の種類に応じて、反応11で用いた鈴木カップリング反応を用いることもできる。 The step of coupling phenylbromopyridine with p-bromoiodobenzene or m-bromoiodobenzene is not limited to the Negishi coupling reaction, and the Suzuki cup used in Reaction 11 depends on the types of available raw materials and reagents. A ring reaction can also be used.
合成の最終工程であるアントラセンのパートとピリジルフェニルブロミドのパートをカップリングする方法として、反応12に示した鈴木カップリング反応の例を取り上げたが、入手できる原料、試薬の種類に応じて根岸カップリング反応を用いてもよい。さらには、本発明の化合物の合成は、アントラセンのパートとフェニレンのパートをカップリングする反応を最終工程にする方法に限られることはない。 The example of the Suzuki coupling reaction shown in Reaction 12 was taken as a method for coupling the anthracene part and the pyridylphenyl bromide part, which are the final steps of the synthesis. A ring reaction may be used. Furthermore, the synthesis of the compound of the present invention is not limited to the method in which the reaction of coupling the anthracene part and the phenylene part is the final step.
アントラセンと連結するための、アルキル基またはシクロアルキル基で置換されたピリジルフェニルブロミドは下記反応15〜16に示したように合成することができる。原料を適宜変更することで、種々のアルキル基またはシクロアルキル基で置換されたピリジルフェニルブロミドを合成することができる。
フェニル基で置換されたピリジルフェニルブロミドは下記反応17〜18に示したように合成することができる。また原料を適宜変更することで、種々のアリール基で置換されたピリジルフェニルブロミドを合成することができる。
<反応で用いる試薬>
鈴木カップリング反応で用いられるパラジウム触媒の具体例としては、テトラキス(トリフェニルホスフィン)パラジウム(0):Pd(PPh3)4、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド:PdCl2(PPh3)2、酢酸パラジウム(II):Pd(OAc)2、トリス(ジベンジリデンアセトン)二パラジウム(0):Pd2(dba)3、トリス(ジベンジリデンアセトン)二パラジウム(0)クロロホルム錯体:Pd2(dba)3・CHCl3、ビス(ジベンジリデンアセトン)パラジウム(0):Pd(dba)2、[1,1’−ビス(ジフェニルホスフィノ)フェロセン]ジクロロパラジウム(II):Pd(dppf)Cl2、PdCl2[P(t−Bu)2−(p−NMe2−Ph)]2などがあげられる。<Reagent used in reaction>
Specific examples of the palladium catalyst used in the Suzuki coupling reaction include tetrakis (triphenylphosphine) palladium (0): Pd (PPh 3 ) 4 , bis (triphenylphosphine) palladium (II) dichloride: PdCl 2 (PPh 3 ) 2 , palladium (II) acetate: Pd (OAc) 2 , tris (dibenzylideneacetone) dipalladium (0): Pd 2 (dba) 3 , tris (dibenzylideneacetone) dipalladium (0) chloroform complex: Pd 2 (Dba) 3 · CHCl 3 , bis (dibenzylideneacetone) palladium (0): Pd (dba) 2 , [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II): Pd (dppf) Cl 2, PdCl 2 [P (t -Bu) 2 - (p-NMe 2 Ph)] 2, and the like.
また、反応を促進させるため、場合によりこれらのパラジウム化合物にホスフィン化合物を加えてもよい。そのホスフィン化合物の具体例としては、トリ(t−ブチル)ホスフィン、トリシクロヘキシルホスフィン、1−(N,N−ジメチルアミノメチル)−2−(ジt−ブチルホスフィノ)フェロセン、1−(N,N−ジブチルアミノメチル)−2−(ジt−ブチルホスフィノ)フェロセン、1−(メトキシメチル)−2−(ジt−ブチルホスフィノ)フェロセン、1,1’−ビス(ジt−ブチルホスフィノ)フェロセン、2,2’−ビス(ジt−ブチルホスフィノ)−1,1’−ビナフチル、2−メトキシ−2’−(ジt−ブチルホスフィノ)−1,1’−ビナフチル、または2−ジシクロヘキシルホスフィノ−2’,6’−ジメトキシビフェニルがあげられる。 In order to accelerate the reaction, a phosphine compound may be added to these palladium compounds in some cases. Specific examples of the phosphine compound include tri (t-butyl) phosphine, tricyclohexylphosphine, 1- (N, N-dimethylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (N, N-dibutylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (methoxymethyl) -2- (di-t-butylphosphino) ferrocene, 1,1′-bis (di-t-butylphos Fino) ferrocene, 2,2′-bis (di-t-butylphosphino) -1,1′-binaphthyl, 2-methoxy-2 ′-(di-t-butylphosphino) -1,1′-binaphthyl, or An example is 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl.
反応で用いられる塩基の具体例としては、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、炭酸水素ナトリウム、水酸化ナトリウム、水酸化カリウム、水酸化バリウム、ナトリウムエトキシド、ナトリウムt−ブトキシド、酢酸ナトリウム、リン酸三カリウム、またはフッ化カリウムがあげられる。 Specific examples of the base used in the reaction include sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, phosphoric acid. Examples include tripotassium or potassium fluoride.
また、反応で用いられる溶媒の具体例としては、ベンゼン、トルエン、キシレン、1,2,4−トリメチルベンゼン、N,N−ジメチルホルムアミド、テトラヒドロフラン、ジエチルエーテル、t−ブチルメチルエーテル、1,4−ジオキサン、メタノール、エタノール、シクロペンチルメチルエーテルまたはイソプロピルアルコールがあげられる。これらの溶媒は適宜選択でき、単独で用いてもよく、混合溶媒として用いてもよい。 Specific examples of the solvent used in the reaction include benzene, toluene, xylene, 1,2,4-trimethylbenzene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butyl methyl ether, 1,4- Examples include dioxane, methanol, ethanol, cyclopentyl methyl ether, and isopropyl alcohol. These solvents can be appropriately selected and may be used alone or as a mixed solvent.
根岸カップリング反応で用いられるパラジウム触媒の具体例としては、テトラキス(トリフェニルホスフィン)パラジウム(0):Pd(PPh3)4、ビス(トリフェニルホスフィン)パラジウム(II)ジクロリド:PdCl2(PPh3)2、酢酸パラジウム(II):Pd(OAc)2、トリス(ジベンジリデンアセトン)二パラジウム(0):Pd2(dba)3、トリス(ジベンジリデンアセトン)二パラジウム(0)クロロホルム錯体:Pd2(dba)3・CHCl3、ビス(ジベンジリデンアセトン)パラジウム(0):Pd(dba)2、ビス(トリt−ブチルホスフィノ)パラジウム(0)、または[1,1’−ビス(ジフェニルホスフィノ)フェロセン]ジクロロパラジウム(II):Pd(dppf)Cl2があげられる。Specific examples of the palladium catalyst used in the Negishi coupling reaction include tetrakis (triphenylphosphine) palladium (0): Pd (PPh 3 ) 4 , bis (triphenylphosphine) palladium (II) dichloride: PdCl 2 (PPh 3 ) 2 , palladium (II) acetate: Pd (OAc) 2 , tris (dibenzylideneacetone) dipalladium (0): Pd 2 (dba) 3 , tris (dibenzylideneacetone) dipalladium (0) chloroform complex: Pd 2 (Dba) 3 · CHCl 3 , bis (dibenzylideneacetone) palladium (0): Pd (dba) 2 , bis (tri-t-butylphosphino) palladium (0), or [1,1′-bis (diphenylphosphine) Fino) ferrocene] dichloropalladium (II): Pd (dppf) Cl 2 is given.
また、反応で用いられる溶媒の具体例としては、ベンゼン、トルエン、キシレン、1,2,4−トリメチルベンゼン、N,N−ジメチルホルムアミド、テトラヒドロフラン、ジエチルエーテル、t−ブチルメチルエーテル、シクロペンチルメチルエーテルまたは1,4−ジオキサンがあげられる。これらの溶媒は適宜選択でき、単独で用いてもよく、混合溶媒として用いてもよい。 Specific examples of the solvent used in the reaction include benzene, toluene, xylene, 1,2,4-trimethylbenzene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butyl methyl ether, cyclopentyl methyl ether or 1,4-dioxane. These solvents can be appropriately selected and may be used alone or as a mixed solvent.
本発明の化合物を、有機EL素子における、電子注入層または電子輸送層に用いた場合、電界印加時において安定である。これらは、本発明の化合物が、電界発光型素子の電子注入材料、または電子輸送材料として優れていることを表す。ここで言う電子注入層とは陰極から有機層へ電子を受け取る層であり、電子輸送層とは注入された電子を発光層へ輸送するための層である。また、電子輸送層が電子注入層を兼ねることも可能である。それぞれの層に用いる材料を、電子注入材料および電子輸送材料という。 When the compound of the present invention is used for an electron injection layer or an electron transport layer in an organic EL device, it is stable when an electric field is applied. These represent that the compound of the present invention is excellent as an electron injecting material or an electron transporting material for an electroluminescent device. The electron injection layer mentioned here is a layer for receiving electrons from the cathode to the organic layer, and the electron transport layer is a layer for transporting the injected electrons to the light emitting layer. The electron transport layer can also serve as the electron injection layer. The material used for each layer is referred to as an electron injection material and an electron transport material.
<有機EL素子の説明>
本願の第2の発明は、電子注入層、または電子輸送層に、本発明の式(1)で表される化合物を含有する有機EL素子である。本発明の有機EL素子は、駆動電圧が低く、駆動時の耐久性が高い。<Description of organic EL element>
2nd invention of this application is an organic EL element containing the compound represented by Formula (1) of this invention in an electron injection layer or an electron carrying layer. The organic EL element of the present invention has a low driving voltage and high durability during driving.
本発明の有機EL素子の構造は各種の態様があるが、基本的には陽極と陰極との間に少なくとも正孔輸送層、発光層、電子輸送層を挟持した多層構造である。素子の具体的な構成の例は、(1)陽極/正孔輸送層/発光層/電子輸送層/陰極、(2)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極、(3)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極、等である。 Although the structure of the organic EL device of the present invention has various modes, it is basically a multilayer structure in which at least a hole transport layer, a light emitting layer, and an electron transport layer are sandwiched between an anode and a cathode. Examples of the specific configuration of the device are (1) anode / hole transport layer / light emitting layer / electron transport layer / cathode, (2) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer. / Cathode, (3) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode, etc.
本発明の化合物は、高い電子注入性および電子輸送性を持っているので、単体又は他の材料と併用して電子注入層、または電子輸送層に使用できる。本発明の有機EL素子は、本発明の電子輸送材料に他の材料を用いた正孔注入層、正孔輸送層、発光層、などを組み合わせることで、青色、緑色、赤色や白色の発光を得ることもできる。 Since the compound of the present invention has high electron injecting property and electron transporting property, it can be used for an electron injecting layer or an electron transporting layer alone or in combination with other materials. The organic EL device of the present invention emits blue, green, red and white light by combining a hole injection layer, a hole transport layer, a light emitting layer, etc. using other materials with the electron transport material of the present invention. It can also be obtained.
本発明の有機EL素子に使用できる発光材料または発光性ドーパントは、高分子学会編、高分子機能材料シリーズ“光機能材料”、共同出版(1991)、P236に記載されているような昼光蛍光材料、蛍光増白剤、レーザー色素、有機シンチレータ、各種の蛍光分析試薬等の発光材料、城戸淳二監修、“有機EL材料とディスプレイ”シーエムシー社出版(2001)P155〜156に記載されているようなドーパント材料、P170〜172に記載されているような3重項材料の発光材料等である。 The light-emitting material or light-emitting dopant that can be used in the organic EL device of the present invention is daylight fluorescence as described in the Polymer Society of Japan, Polymer Functional Materials Series “Optical Functional Materials”, Joint Publication (1991), P236. Materials, fluorescent brighteners, laser dyes, organic scintillators, various fluorescent analysis reagents and other luminescent materials, supervised by Koji Koji, “Organic EL materials and displays” published by CMC Publishing Co., Ltd. (2001) P155-156 And a light emitting material of a triplet material as described in P170 to 172.
発光材料または発光性ドーパントとして使用できる化合物は、多環芳香族化合物、ヘテロ芳香族化合物、有機金属錯体、色素、高分子系発光材料、スチリル誘導体、芳香族アミン誘導体、クマリン誘導体、ボラン誘導体、オキサジン誘導体、スピロ環を有する化合物、オキサジアゾール誘導体、フルオレン誘導体等である。多環芳香族化合物の例は、アントラセン誘導体、フェナントレン誘導体、ナフタセン誘導体、ピレン誘導体、クリセン誘導体、ペリレン誘導体、コロネン誘導体、ルブレン誘導体等である。ヘテロ芳香族化合物の例は、ジアルキルアミノ基またはジアリールアミノ基を有するオキサジアゾール誘導体、ピラゾロキノリン誘導体、ピリジン誘導体、ピラン誘導体、フェナントロリン誘導体、シロール誘導体、トリフェニルアミノ基を有するチオフェン誘導体、キナクリドン誘導体等である。有機金属錯体の例は、亜鉛、アルミニウム、ベリリウム、ユーロピウム、テルビウム、ジスプロシウム、イリジウム、白金、オスミウム、金、等と、キノリノール誘導体、ベンゾキサゾ−ル誘導体、ベンゾチアゾール誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、ベンゾイミダゾール誘導体、ピロール誘導体、ピリジン誘導体、フェナントロリン誘導体等との錯体である。色素の例は、キサンテン誘導体、ポリメチン誘導体、ポルフィリン誘導体、クマリン誘導体、ジシアノメチレンピラン誘導体、ジシアノメチレンチオピラン誘導体、オキソベンズアントラセン誘導体、カルボスチリル誘導体、ペリレン誘導体、ベンゾオキサゾール誘導体、ベンゾチアゾール誘導体、ベンゾイミダゾール誘導体等の色素が挙げられる。高分子系発光材料の例は、ポリパラフェニルビニレン誘導体、ポリチオフェン誘導体、ポリビニルカルバゾ−ル誘導体、ポリシラン誘導体、ポリフルオレン誘導体、ポリパラフェニレン誘導体等である。スチリル誘導体の例は、アミン含有スチリル誘導体、スチリルアリーレン誘導体等である。 The compounds that can be used as the light emitting material or the light emitting dopant are polycyclic aromatic compounds, heteroaromatic compounds, organometallic complexes, dyes, polymer light emitting materials, styryl derivatives, aromatic amine derivatives, coumarin derivatives, borane derivatives, oxazines. Derivatives, compounds having a spiro ring, oxadiazole derivatives, fluorene derivatives and the like. Examples of the polycyclic aromatic compound are anthracene derivatives, phenanthrene derivatives, naphthacene derivatives, pyrene derivatives, chrysene derivatives, perylene derivatives, coronene derivatives, rubrene derivatives, and the like. Examples of heteroaromatic compounds are oxadiazole derivatives having a dialkylamino group or diarylamino group, pyrazoloquinoline derivatives, pyridine derivatives, pyran derivatives, phenanthroline derivatives, silole derivatives, thiophene derivatives having a triphenylamino group, quinacridone derivatives Etc. Examples of organometallic complexes are zinc, aluminum, beryllium, europium, terbium, dysprosium, iridium, platinum, osmium, gold, etc., quinolinol derivatives, benzoxazole derivatives, benzothiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, A complex with a benzimidazole derivative, a pyrrole derivative, a pyridine derivative, a phenanthroline derivative, or the like. Examples of dyes are xanthene derivatives, polymethine derivatives, porphyrin derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, oxobenzanthracene derivatives, carbostyril derivatives, perylene derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazoles And pigments such as derivatives. Examples of the polymer light-emitting material include polyparaphenyl vinylene derivatives, polythiophene derivatives, polyvinyl carbazole derivatives, polysilane derivatives, polyfluorene derivatives, polyparaphenylene derivatives, and the like. Examples of styryl derivatives are amine-containing styryl derivatives, styrylarylene derivatives, and the like.
本発明の有機EL素子に使用される他の電子輸送材料は、光導電材料において電子伝達化合物として使用できる化合物、有機EL素子の電子輸送層および電子注入層に使用できる化合物の中から任意に選択して用いることができる。 Other electron transport materials used in the organic EL device of the present invention are arbitrarily selected from compounds that can be used as electron transport compounds in photoconductive materials and compounds that can be used in the electron transport layer and electron injection layer of organic EL devices. Can be used.
このような電子輸送材料の具体例は、キノリノール系金属錯体、2,2’−ビピリジル誘導体、フェナントロリン誘導体、ジフェニルキノン誘導体、ペリレン誘導体、オキサジアゾール誘導体、チオフェン誘導体、トリアゾール誘導体、チアジアゾール誘導体、オキシン誘導体の金属錯体、キノキサリン誘導体、キノキサリン誘導体のポリマー、ベンザゾール類化合物、ガリウム錯体、ピラゾール誘導体、パ−フルオロ化フェニレン誘導体、トリアジン誘導体、ピラジン誘導体、ベンゾキノリン誘導体、イミダゾピリジン誘導体、ボラン誘導体等である。 Specific examples of such electron transport materials include quinolinol metal complexes, 2,2′-bipyridyl derivatives, phenanthroline derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, oxine derivatives. Metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, and the like.
本発明の有機EL素子に使用される正孔注入材料および正孔輸送材料については、光導電材料において、正孔の電荷輸送材料として従来から慣用されている化合物や、有機EL素子の正孔注入層および正孔輸送層に使用されている公知のものの中から任意のものを選択して用いることができる。それらの具体例は、カルバゾ−ル誘導体、トリアリールアミン誘導体、フタロシアニン誘導体等である。 Regarding the hole injection material and the hole transport material used in the organic EL device of the present invention, in a photoconductive material, a compound conventionally used as a charge transport material for holes or a hole injection of an organic EL device is used. Any known material used for the layer and the hole transport layer can be selected and used. Specific examples thereof are carbazole derivatives, triarylamine derivatives, phthalocyanine derivatives and the like.
本発明の有機EL素子を構成する各層は、各層を構成すべき材料を蒸着法、スピンコート法またはキャスト法等の方法で薄膜とすることにより、形成することができる。このようにして形成された各層の膜厚については特に限定はなく、材料の性質に応じて適宜設定することができるが、通常2nm〜5000nmの範囲である。なお、発光材料を薄膜化する方法は、均質な膜が得やすく、かつピンホールが生成しにくい等の点から蒸着法を採用するのが好ましい。蒸着法を用いて薄膜化する場合、その蒸着条件は、本発明の発光材料の種類により異なる。蒸着条件は一般的に、ボート加熱温度50〜400℃、真空度10−6〜10−3Pa、蒸着速度0.01〜50nm/秒、基板温度−150〜+300℃、膜厚5nm〜5μmの範囲で適宜設定することが好ましい。Each layer constituting the organic EL element of the present invention can be formed by forming a material to constitute each layer into a thin film by a method such as a vapor deposition method, a spin coating method, or a casting method. The thickness of each layer formed in this way is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. Note that it is preferable to employ a vapor deposition method as a method of thinning the light emitting material from the standpoint that a homogeneous film can be easily obtained and pinholes are hardly generated. When thinning using the vapor deposition method, the vapor deposition conditions differ depending on the type of the light emitting material of the present invention. Deposition conditions generally include a boat heating temperature of 50 to 400 ° C., a degree of vacuum of 10 −6 to 10 −3 Pa, a deposition rate of 0.01 to 50 nm / second, a substrate temperature of −150 to + 300 ° C., and a film thickness of 5 nm to 5 μm. It is preferable to set appropriately within the range.
本発明の有機EL素子は、前記のいずれの構造であっても、基板に支持されていることが好ましい。基板は機械的強度、熱安定性および透明性を有するものであればよく、ガラス、透明プラスチックフィルム等を用いることができる。陽極物質は4eVより大きな仕事関数を有する金属、合金、電気伝導性化合物およびこれらの混合物を用いることができる。その具体例は、Au等の金属、CuI、インジウムチンオキシド(以下、ITOと略記する)、SnO2、ZnO等である。The organic EL device of the present invention is preferably supported by a substrate in any of the structures described above. The substrate only needs to have mechanical strength, thermal stability, and transparency, and glass, a transparent plastic film, and the like can be used. As the anode material, metals, alloys, electrically conductive compounds and mixtures thereof having a work function larger than 4 eV can be used. Specific examples thereof include metals such as Au, CuI, indium tin oxide (hereinafter abbreviated as ITO), SnO 2 , ZnO, and the like.
陰極物質は4eVより小さな仕事関数の金属、合金、電気伝導性化合物、およびこれらの混合物を使用できる。その具体例は、アルミニウム、カルシウム、マグネシウム、リチウム、マグネシウム合金、アルミニウム合金等である。合金の具体例は、アルミニウム/弗化リチウム、アルミニウム/リチウム、マグネシウム/銀、マグネシウム/インジウム等である。有機EL素子の発光を効率よく取り出すために、電極の少なくとも一方は光透過率を10%以上にすることが望ましい。電極としてのシート抵抗は数百Ω/□以下にすることが好ましい。なお、膜厚は電極材料の性質にもよるが、通常10nm〜1μm、好ましくは10〜400nmの範囲に設定される。このような電極は、上述の電極物質を使用して、蒸着やスパッタリング等の方法で薄膜を形成させることにより作製することができる。 Cathode materials can use metals, alloys, electrically conductive compounds, and mixtures thereof with work functions of less than 4 eV. Specific examples thereof are aluminum, calcium, magnesium, lithium, magnesium alloy, aluminum alloy and the like. Specific examples of the alloy include aluminum / lithium fluoride, aluminum / lithium, magnesium / silver, and magnesium / indium. In order to efficiently extract light emitted from the organic EL element, it is desirable that at least one of the electrodes has a light transmittance of 10% or more. The sheet resistance as the electrode is preferably several hundred Ω / □ or less. Although the film thickness depends on the properties of the electrode material, it is usually set in the range of 10 nm to 1 μm, preferably 10 to 400 nm. Such an electrode can be produced by forming a thin film by a method such as vapor deposition or sputtering using the electrode material described above.
次に、本発明の発光材料を用いて有機EL素子を作成する方法の一例として、前述の陽極/正孔注入層/正孔輸送層/発光層/本発明の電子輸送材料/陰極からなる有機EL素子の作成法について説明する。適当な基板上に、陽極材料の薄膜を蒸着法により形成させて陽極を作製した後、この陽極上に正孔注入層および正孔輸送層の薄膜を形成させる。この上に発光層の薄膜を形成させる。この発光層の上に本発明の電子輸送材料を真空蒸着し、薄膜を形成させ、電子輸送層とする。さらに陰極用物質からなる薄膜を蒸着法により形成させて陰極とすることにより、目的の有機EL素子が得られる。なお、上述の有機EL素子の作製においては、作製順序を逆にして、陰極、電子輸送層、発光層、正孔輸送層、正孔注入層、陽極の順に作製することも可能である。 Next, as an example of a method for producing an organic EL device using the light emitting material of the present invention, an organic material comprising the above-mentioned anode / hole injection layer / hole transport layer / light emitting layer / electron transport material of the present invention / cathode is used. A method for creating an EL element will be described. A thin film of an anode material is formed on a suitable substrate by vapor deposition to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A light emitting layer thin film is formed thereon. On this light emitting layer, the electron transport material of this invention is vacuum-deposited, a thin film is formed and it is set as an electron carrying layer. Furthermore, the target organic EL element is obtained by forming the thin film which consists of a substance for cathodes by a vapor deposition method, and making it a cathode. In the production of the organic EL element described above, the production order can be reversed, and the cathode, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be produced in this order.
このようにして得られた有機EL素子に直流電圧を印加する場合には、陽極を+、陰極を−の極性として印加すればよく、電圧2〜40V程度を印加すると、透明又は半透明の電極側(陽極又は陰極、および両方)より発光が観測できる。また、この有機EL素子は、交流電圧を印加した場合にも発光する。なお、印加する交流の波形は任意でよい。 When a DC voltage is applied to the organic EL device thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, a transparent or translucent electrode is applied. Luminescence can be observed from the side (anode or cathode and both). The organic EL element also emits light when an alternating voltage is applied. The alternating current waveform to be applied may be arbitrary.
以下に、本発明を実施例に基づいて更に詳しく説明する。まず、実施例で用いた化合物の合成例について、以下に説明する。 Hereinafter, the present invention will be described in more detail based on examples. First, synthesis examples of the compounds used in the examples are described below.
[合成例1]化合物(1−1−1)の合成
<4−(4−ブロモフェニル)ピリジンの合成>
<4−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジン:化合物(1−1−1)の合成>
1H−NMR(CDCl3): δ=8.8〜8.7(dd、2H)、 8.1(d、1H)、 8.0(d、1H)、 7.9(m、2H)、 7.8(d、2H)、 7.7(m、4H)、 7.7〜7.6(m、1H)、 7.6(dd、1H)、 7.5(m、3H)、 7.4〜7.3(m、2H)、 7.3〜7.2(m、3H)、 7.2(m、1H).<4- (4- (10- (Naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine: Synthesis of Compound (1-1-1)>
1 H-NMR (CDCl 3 ): δ = 8.8 to 8.7 (dd, 2H), 8.1 (d, 1H), 8.0 (d, 1H), 7.9 (m, 2H) , 7.8 (d, 2H), 7.7 (m, 4H), 7.7 to 7.6 (m, 1H), 7.6 (dd, 1H), 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 3H), 7.2 (m, 1H).
[合成例2]化合物(1−1−2)の合成
<3−(4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)フェニル)ピリジンの合成>
<3−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジン:化合物(1−1−2)の合成>
1H−NMR(CDCl3): δ=9.1(d、1H)、 8.7(dd、1H)、 8.1(m、2H)、 8.0(d、1H)、 7.9〜7.8(m、2H)、 7.8(d、2H)、 7.7(m、2H)、 7.7〜7.6(m、1H)、 7.6(m、1H)、 7.5〜7.4(m、4H)、 7.4〜7.3(m、2H)、 7.3〜7.2(m、3H)、 7.2(m、1H).<3- (4- (10- (Naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine: Synthesis of Compound (1-1-2)>
1 H-NMR (CDCl 3 ): δ = 9.1 (d, 1H), 8.7 (dd, 1H), 8.1 (m, 2H), 8.0 (d, 1H), 7.9 7.8 (m, 2H), 7.8 (d, 2H), 7.7 (m, 2H), 7.7 to 7.6 (m, 1H), 7.6 (m, 1H), 7.5-7.4 (m, 4H), 7.4-7.3 (m, 2H), 7.3-7.2 (m, 3H), 7.2 (m, 1H).
[合成例3]化合物(1−1−3)の合成
<2−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3): δ=8.8(m、1H)、 8.3(m、2H)、 8.1(d、1H)、 8.0(d、1H)、 7.9(m、1H)、 7.9〜7.8(m、3H)、 7.7〜7.6(m、3H)、 7.6(m、1H)、 7.5〜7.4(m、3H)、 7.3(m、3H)、 7.2(m、4H).Synthesis Example 3 Synthesis of Compound (1-1-3) <Synthesis of 2- (4- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ): δ = 8.8 (m, 1H), 8.3 (m, 2H), 8.1 (d, 1H), 8.0 (d, 1H), 7.9 (M, 1H), 7.9-7.8 (m, 3H), 7.7-7.6 (m, 3H), 7.6 (m, 1H), 7.5-7.4 (m 3H), 7.3 (m, 3H), 7.2 (m, 4H).
[合成例4]化合物(1−1−134)の合成
<9−(4−メトキシフェニル)−10−(ナフタレン−1−イル)アントラセンの合成>
<4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェノールの合成>
<4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル トリフルオロメタンスルホナートの合成>
<4,4,5,5−テトラメチル−2−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)−1,3,2−ジオキサボロランの合成>
<2−メチル−3−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジン:化合物(1−1−134)の合成>
1H−NMR(CDCl3): δ=8.6(dd、1H)、 8.1(d、1H)、 8.0(d、1H)、 7.8(d、2H)、 7.8〜7.7(m、2H)、 7.7(m、1H)、 7.6(m、4H)、 7.5(m、3H)、 7.4〜7.3(m、2H)、 7.3〜7.2(m、5H)、 2.7(s、3H).<2-Methyl-3- (4- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine: Synthesis of Compound (1-1-134)>
1 H-NMR (CDCl 3 ): δ = 8.6 (dd, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.8 (d, 2H), 7.8 ˜7.7 (m, 2H), 7.7 (m, 1H), 7.6 (m, 4H), 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3-7.2 (m, 5H), 2.7 (s, 3H).
[合成例5]化合物(1−1−153)の合成
<4−メチル−3−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3): δ=8.7(m、1H)、 8.5(m、1H)、 8.1(d、1H)、 8.0(d、1H)、 7.8(m、2H)、 7.7〜7.6(m、6H)、 7.5(m、3H)、 7.4〜7.3(m、2H)、 7.3〜7.2(m、5H)、 2.5(s、3H).Synthesis Example 5 Synthesis of Compound (1-1-153) <Synthesis of 4-methyl-3- (4- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ): δ = 8.7 (m, 1H), 8.5 (m, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.8 (M, 2H), 7.7 to 7.6 (m, 6H), 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m 5H), 2.5 (s, 3H).
[合成例6]化合物(1−1−172)の合成
<3−メチル−5−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3): δ=8.7(d、1H)、 8.5(s、1H)、 8.1(d、1H)、 8.0(d、1H)、 7.9〜7.8(m、3H)、 7.8(d、2H)、 7.7(m、2H)、 7.6(m、1H)、 7.6(m、1H)、 7.5(m、3H)、 7.4〜7.3(m、2H)、 7.3〜7.2(m、4H)、 2.5(s、3H).[Synthesis Example 6] Synthesis of Compound (1-1-172) <Synthesis of 3-methyl-5- (4- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ): δ = 8.7 (d, 1H), 8.5 (s, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.9 ˜7.8 (m, 3H), 7.8 (d, 2H), 7.7 (m, 2H), 7.6 (m, 1H), 7.6 (m, 1H), 7.5 ( m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 4H), 2.5 (s, 3H).
[合成例7]化合物(1−1−191)の合成
<2−メチル−5−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3): δ=8.9(d、1H)、 8.1(d、1H)、 8.0(d、1H)、 8.0(dd、1H)、 7.9〜7.8(m、2H)、 7.8(d、2H)、 7.7(m、2H)、 7.6(m、1H)、 7.6(m、1H)、 7.5(m、3H)、 7.4〜7.3(m、3H)、 7.3〜7.2(m、4H)、 2.7(s、3H).Synthesis Example 7 Synthesis of Compound (1-1-191) <Synthesis of 2-methyl-5- (4- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ): δ = 8.9 (d, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 8.0 (dd, 1H), 7.9 ˜7.8 (m, 2H), 7.8 (d, 2H), 7.7 (m, 2H), 7.6 (m, 1H), 7.6 (m, 1H), 7.5 ( m, 3H), 7.4 to 7.3 (m, 3H), 7.3 to 7.2 (m, 4H), 2.7 (s, 3H).
[合成例8]化合物(1−1−210)の合成
<2−メチル−4−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3) δ=8.6(d、1H)、 8.1(d、1H)、 8.0(d、1H)、 7.9(m、2H)、 7.8(d、2H)、 7.7(m、2H)、 7.7〜7.6(m、1H)、 7.6(m、2H)、 7.5(m、4H)、 7.4〜7.3(m、2H)、 7.3〜7.2(m、4H)、 2.7(s、3H).Synthesis Example 8 Synthesis of Compound (1-1-210) <Synthesis of 2-methyl-4- (4- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ) δ = 8.6 (d, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.9 (m, 2H), 7.8 ( d, 2H), 7.7 (m, 2H), 7.7 to 7.6 (m, 1H), 7.6 (m, 2H), 7.5 (m, 4H), 7.4 to 7 .3 (m, 2H), 7.3-7.2 (m, 4H), 2.7 (s, 3H).
[合成例9]化合物(1−1−229)の合成
<3−メチル−4−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3): δ=8.6(s、1H)、 8.6(d、1H)、 8.1(d、1H)、 8.0(d、1H)、 7.8(d、2H)、 7.7(m、1H)、 7.7(m、1H)、 7.6(m、4H)、 7.5(m、3H)、 7.4(m、3H)、 7.4〜7.2(m、4H)、 2.5(s、3H).Synthesis Example 9 Synthesis of Compound (1-1-229) <Synthesis of 3-methyl-4- (4- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ): δ = 8.6 (s, 1H), 8.6 (d, 1H), 8.1 (d, 1H), 8.0 (d, 1H), 7.8 (D, 2H), 7.7 (m, 1H), 7.7 (m, 1H), 7.6 (m, 4H), 7.5 (m, 3H), 7.4 (m, 3H) 7.4-7.2 (m, 4H), 2.5 (s, 3H).
[合成例10]化合物(1−2−1)の合成
<4−(3−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3): δ=8.7(dt、2H)、 8.1(d、1H)、8.0(d、1H)、 7.9〜7.6(m、10H)、 7.5(m、3H)、 7.4〜7.3(m、2H)、 7.3〜7.2(m、4H).Synthesis Example 10 Synthesis of Compound (1-2-1) <Synthesis of 4- (3- (10- (Naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ): δ = 8.7 (dt, 2H), 8.1 (d, 1H), 8.0 (d, 1H), 7.9 to 7.6 (m, 10H) 7.5 (m, 3H), 7.4 to 7.3 (m, 2H), 7.3 to 7.2 (m, 4H).
[合成例11]化合物(1−2−153)の合成
<4−メチル−3−(3−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3): δ=8.6(d、1H)、 8.5(dd、1H)、 8.1(d、1H)、 8.0(dd、1H)、 7.8(d、2H)、 7.8〜7.7(m、2H)、 7.6〜7.4(m、7H)、 7.4〜7.3(m、2H)、 7.2〜7.1(m、5H)、 2.4(d、3H).Synthesis Example 11 Synthesis of Compound (1-2153) <Synthesis of 4-methyl-3- (3- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ): δ = 8.6 (d, 1H), 8.5 (dd, 1H), 8.1 (d, 1H), 8.0 (dd, 1H), 7.8 (D, 2H), 7.8 to 7.7 (m, 2H), 7.6 to 7.4 (m, 7H), 7.4 to 7.3 (m, 2H), 7.2 to 7 .1 (m, 5H), 2.4 (d, 3H).
[合成例12]化合物(1−2−172)の合成
<3−メチル−5−(3−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)ピリジンの合成>
1H−NMR(CDCl3): δ=8.8(d、1H)、 8.5〜8.4(m、1H)、 8.1(d、1H)、 8.0(d、1H)、 7.8〜7.7(m、7H)、 7.6(m、2H)、 7.5(m、3H)、 7.3(t、2H)、 7.3〜7.2(m、4H)、 2.4(d、3H).Synthesis Example 12 Synthesis of Compound (1-2172) <Synthesis of 3-methyl-5- (3- (10- (naphthalen-1-yl) anthracen-9-yl) phenyl) pyridine>
1 H-NMR (CDCl 3 ): δ = 8.8 (d, 1H), 8.5 to 8.4 (m, 1H), 8.1 (d, 1H), 8.0 (d, 1H) 7.8-7.7 (m, 7H), 7.6 (m, 2H), 7.5 (m, 3H), 7.3 (t, 2H), 7.3-7.2 (m 4H), 2.4 (d, 3H).
原料の化合物を適宜変更することにより、上述した合成例に準じた方法で、本発明の他の誘導体化合物を合成することができる。 By appropriately changing the raw material compound, other derivative compounds of the present invention can be synthesized by a method according to the synthesis example described above.
以下、本発明をさらに詳細に説明するために、本発明の化合物を用いた有機EL素子の実施例を示すが、本発明はこれらに限定されるものではない。 Hereinafter, in order to describe the present invention in more detail, examples of the organic EL device using the compound of the present invention are shown, but the present invention is not limited thereto.
実施例1および比較例1に係る有機EL素子を作製し、それぞれ、定電流駆動試験における駆動開始電圧(V)、初期輝度の90%以上の輝度を保持する時間(hr)の測定を行った。以下、実施例および比較例について詳細に説明する。 The organic EL elements according to Example 1 and Comparative Example 1 were manufactured, and the driving start voltage (V) in the constant current driving test and the time (hr) for maintaining the luminance of 90% or more of the initial luminance were measured. . Hereinafter, examples and comparative examples will be described in detail.
作製した実施例1および比較例1、2に係る電界発光素子における、各層の材料構成を下記表1に示す。
表1において、「HI」はN4,N4’−ジフェニル−N4,N4’−ビス(9−フェニル−9H−カルバゾール−3−イル)−[1、1’−ビフェニル]−4、4’−ジアミン、「NPD」はN,N’−ジフェニル−N,N’−ジナフチル−4,4’−ジアミノビフェニル、化合物(A)は9−フェニル−10−(4−フェニルナフタレン−1−イル)アントラセン、化合物(B)はN5,N5,N9,N9−7,7−ヘキサフェニル−7H−ベンゾ〔C〕フルオレン−5,9−ジアミンであり、化合物(C)は9,10−ビス(4−(ピリジン−2−イル)ナフタレン−1−イル)アントラセンである。陰極の形成に用いたリチウム 8−キノリノラート(Liq)と共に化学構造を以下に示す。In Table 1, “HI” is N 4 , N 4 ′ -diphenyl-N 4 , N 4 ′ -bis (9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl] -4, 4′-diamine, “NPD” is N, N′-diphenyl-N, N′-dinaphthyl-4,4′-diaminobiphenyl, compound (A) is 9-phenyl-10- (4-phenylnaphthalene-1- yl) anthracene compound (B) is N 5, N 5, N 9 , N 9 -7,7- hexaphenyl -7H- benzo [C] fluorene-5,9-diamine, compound (C) 9 , 10-bis (4- (pyridin-2-yl) naphthalen-1-yl) anthracene. A chemical structure is shown below with lithium 8-quinolinolato (Liq) used for formation of a cathode.
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨して得られる26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置(真空機工(株)製)の基板ホルダーに固定し、HIを入れたモリブデン製蒸着用ボート、NPDを入れたモリブデン製蒸着用ボート、化合物(A)を入れたモリブデン製蒸着用ボート、化合物(B)を入れたモリブデン製蒸着用ボート、化合物(1−1−1)を入れたモリブデン製蒸着用ボート、Liqを入れたモリブデン製蒸着用ボート、銀を入れたモリブデン製蒸着用ボート、およびマグネシウムを入れたモリブデン製蒸着用ボートを装着した。 A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO deposited to a thickness of 180 nm by sputtering to 150 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Vacuum Kiko Co., Ltd.), and a molybdenum vapor deposition boat containing HI, a molybdenum vapor deposition boat containing NPD, and compound (A) are placed therein. Molybdenum vapor deposition boat, molybdenum vapor deposition boat containing compound (B), molybdenum vapor deposition boat containing compound (1-1-1), molybdenum vapor deposition boat containing Liq, silver A molybdenum vapor deposition boat and a molybdenum vapor deposition boat containing magnesium were installed.
透明支持基板のITO膜の上に順次、下記各層を形成した。真空槽を5×10−4Paまで減圧し、まず、HIが入った蒸着用ボートを加熱して膜厚40nmになるように蒸着して正孔注入層を形成し、次いで、NPDが入った蒸着用ボートを加熱して膜厚25nmになるように蒸着して正孔輸送層を形成した。次に、化合物(A)が入った蒸着用ボートと化合物(B)の入った蒸着用ボートを同時に加熱して、膜厚25nmになるように蒸着して発光層を形成した。このとき化合物(A)と化合物(B)の重量比がおよそ95対5になるように蒸着速度を調節した。次に化合物(1−1−1)の入った蒸着用ボートを加熱して膜厚25nmになるように蒸着して電子輸送層を形成した。各層の蒸着速度は0.01〜1nm/秒であった。The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5 × 10 −4 Pa, first, a vapor deposition boat containing HI was heated to deposit to a film thickness of 40 nm to form a hole injection layer, and then NPD entered. The vapor deposition boat was heated and vapor-deposited to a film thickness of 25 nm to form a hole transport layer. Next, the vapor deposition boat containing the compound (A) and the vapor deposition boat containing the compound (B) were heated at the same time and vapor-deposited to a film thickness of 25 nm to form a light emitting layer. At this time, the deposition rate was adjusted so that the weight ratio of the compound (A) to the compound (B) was about 95: 5. Next, the evaporation boat containing the compound (1-1-1) was heated and evaporated to a film thickness of 25 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm / second.
その後、Liq入りの蒸着用ボートを加熱して膜厚1nmになるように0.003〜0.1nm/秒の蒸着速度で蒸着した。次いで、銀が入った蒸着用ボートとマグネシウムの入った蒸着用ボートを同時に加熱し、銀とマグネシウムの原子数の比がおよそ1対9になるように蒸着速度を0.01〜10nm/秒の間で調節して、膜厚100nmになるように蒸着することにより陰極を形成し、有機EL素子を得た。 Thereafter, the evaporation boat containing Liq was heated and evaporated at a deposition rate of 0.003 to 0.1 nm / second so as to have a film thickness of 1 nm. Next, the deposition boat containing silver and the deposition boat containing magnesium are heated at the same time, and the deposition rate is set to 0.01 to 10 nm / second so that the ratio of the number of atoms of silver and magnesium is about 1: 9. The cathode was formed by vapor-depositing so as to have a film thickness of 100 nm, and an organic EL device was obtained.
ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、直流電圧を印加すると、波長約455nmの青色発光を得た。また、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は4.23Vで、初期輝度の90%以上の輝度を保持する時間は71時間だった。When a direct current voltage was applied using the ITO electrode as the anode and the Liq / magnesium-silver alloy electrode as the cathode, blue light emission with a wavelength of about 455 nm was obtained. In addition, a constant current driving test was performed at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 4.23 V, and the time for maintaining a luminance of 90% or more of the initial luminance was 71 hours.
<比較例1>
化合物(1−1−1)を化合物(C)に替えた以外は実施例1に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.73Vで、初期輝度の90%以上の輝度を保持する時間は1時間だった。<Comparative Example 1>
An organic EL device was obtained by the method according to Example 1 except that the compound (1-1-1) was changed to the compound (C). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The drive test start voltage was 3.73 V, and the time for maintaining a luminance of 90% or more of the initial luminance was 1 hour.
以上の結果を表2にまとめた。
さらに、実施例2〜12および比較例2、3に係る有機EL素子を作製し、それぞれ、定電流駆動試験における駆動開始電圧(V)、初期値の90%以上の輝度を保持する時間(hr)の測定を行った。以下、実施例および比較例について詳細に説明する。 Furthermore, the organic EL elements according to Examples 2 to 12 and Comparative Examples 2 and 3 were manufactured, and the driving start voltage (V) in the constant current driving test and the time for maintaining the luminance of 90% or more of the initial value (hr), respectively. ) Was measured. Hereinafter, examples and comparative examples will be described in detail.
作製した実施例2〜12および比較例2、3に係る有機EL素子における、各層の材料構成を下記表3に示す。
表3において、「HI」はN4,N4’−ジフェニル−N4,N4’−ビス(9−フェニル−9H−カルバゾール−3−イル)−[1、1’−ビフェニル]−4、4’−ジアミン、HTはN−([1,1’−ビフェニル]−4−イル)−9,9−ジメチル−N−(4−(9−フェニル−9H−カルバゾール−3−イル)フェニル)−9H−フルオレン−2−アミン、化合物(D)は9−(4−(ナフタレン−1−イル)フェニル)−10−フェニルアントラセン、化合物(E)は4,4’−((7,7−ジフェニル−7H−ベンゾ[c]フルオレン−5,9−ジイル)ビス(フェニルアミノ))ジベンゾニトリル、化合物(F)は4’−(4−(10−(ナフタレン−2−イル)アントラセン−9−イル)フェニル)−2,2’:6’,2”−テルピリジン、化合物(G)は5−(4−(10−(ナフタレン−1−イル)アントラセン−9−イル)フェニル)−2,4’−ビピリジンである。In Table 3, “HI” is N 4 , N 4 ′ -diphenyl-N 4 , N 4 ′ -bis (9-phenyl-9H-carbazol-3-yl)-[1,1′-biphenyl] -4, 4'-diamine, HT is N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine, compound (D) is 9- (4- (naphthalen-1-yl) phenyl) -10-phenylanthracene, compound (E) is 4,4 ′-((7,7- Diphenyl-7H-benzo [c] fluorene-5,9-diyl) bis (phenylamino)) dibenzonitrile, compound (F) is 4 ′-(4- (10- (naphthalen-2-yl) anthracene-9- Yl) phenyl) -2,2 ': 6', 2 "-tel Lysine, compound (G) is a 5- (4- (10- (naphthalene-1-yl) anthracene-9-yl) phenyl) 2,4'-bipyridine.
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨して得られる26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置(昭和真空(株)製)の基板ホルダーに固定し、HIを入れたモリブデン製蒸着用ボート、HTを入れたモリブデン製蒸着用ボート、化合物(D)を入れたモリブデン製蒸着用ボート、化合物(E)を入れたモリブデン製蒸着用ボート、化合物(1−1−1)を入れたモリブデン製蒸着用ボート、Liqを入れたモリブデン製蒸着用ボート、マグネシウムを入れたモリブデンボートおよび銀を入れたタングステン製蒸着用ボートを装着した。 A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) obtained by polishing ITO deposited to a thickness of 180 nm by sputtering to 150 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum vapor deposition boat containing HI, a molybdenum vapor deposition boat containing HT, and compound (D) are placed therein. Molybdenum deposition boat, molybdenum deposition boat containing compound (E), molybdenum deposition boat containing compound (1-1-1), molybdenum deposition boat containing Liq, magnesium A molybdenum boat and a tungsten evaporation boat containing silver were installed.
透明支持基板のITO膜の上に順次、下記各層を形成した。真空槽を5×10−4Paまで減圧し、まず、HIが入った蒸着用ボートを加熱して膜厚40nmになるように蒸着して正孔注入層を形成し、次いで、HTが入った蒸着用ボートを加熱して膜厚30nmになるように蒸着して正孔輸送層を形成した。次に、化合物(E)が入った蒸着用ボートと化合物(F)の入った蒸着用ボートを同時に加熱して、膜厚35nmになるように蒸着して発光層を形成した。このとき化合物(D)と化合物(E)の重量比がおよそ95対5になるように蒸着速度を調節した。次に、化合物(1−1−1)の入った蒸着用ボートとLiqの入った蒸着用ボートを同時に加熱して膜厚25nmになるように蒸着して電子輸送層を形成した。化合物(1−1−1)とLiqの重量比がおよそ1:1になるように蒸着速度を調節した。各層の蒸着速度は0.01〜1nm/秒であった。The following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5 × 10 −4 Pa, and first, a vapor deposition boat containing HI was heated to deposit to a film thickness of 40 nm to form a hole injection layer, and then HT entered. The vapor deposition boat was heated and vapor-deposited so that it might become a film thickness of 30 nm, and the positive hole transport layer was formed. Next, the vapor deposition boat containing the compound (E) and the vapor deposition boat containing the compound (F) were heated at the same time and vapor-deposited to a film thickness of 35 nm to form a light emitting layer. At this time, the deposition rate was adjusted so that the weight ratio of the compound (D) to the compound (E) was about 95: 5. Next, the vapor deposition boat containing the compound (1-1-1) and the vapor deposition boat containing Liq were heated at the same time to be vapor-deposited to a film thickness of 25 nm to form an electron transport layer. The deposition rate was adjusted so that the weight ratio of the compound (1-1-1) and Liq was approximately 1: 1. The deposition rate of each layer was 0.01 to 1 nm / second.
その後、Liqが入った蒸着用ボートを加熱して膜厚1nmになるように0.01〜0.1nm/秒の蒸着速度で蒸着した。次いで、マグネシウムの入ったボートと銀の入ったボートを同時に加熱し、銀とマグネシウムの原子数比が1対10となるように蒸着速度が0.1〜10nm/秒の間で調整して、膜厚100nmになるように蒸着することにより陰極を形成し、有機EL素子を得た。 Thereafter, the evaporation boat containing Liq was heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm. Next, the magnesium-containing boat and the silver-containing boat are heated at the same time, and the deposition rate is adjusted between 0.1 to 10 nm / second so that the atomic ratio of silver to magnesium is 1:10. A cathode was formed by vapor deposition so as to have a film thickness of 100 nm to obtain an organic EL element.
ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、直流電圧を印加すると、波長約450nmの青色発光を得た。また、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.89Vで、初期輝度の90%以上の輝度を保持する時間は61時間だった。When a direct current voltage was applied using the ITO electrode as the anode and the Liq / magnesium-silver alloy electrode as the cathode, blue light emission with a wavelength of about 450 nm was obtained. In addition, a constant current driving test was performed at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test starting voltage was 3.89 V, and the time for maintaining 90% or more of the initial luminance was 61 hours.
化合物(1−1−1)を化合物(1−1−2)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.79Vで、初期輝度の90%以上の輝度を保持する時間は60時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-1-2). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The drive test start voltage was 3.79 V, and the time for maintaining a luminance of 90% or more of the initial luminance was 60 hours.
化合物(1−1−1)を化合物(1−1−134)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.86Vで、初期輝度の90%以上の輝度を保持する時間は177時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-1-134). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 3.86 V, and the time for maintaining 90% or more of the initial luminance was 177 hours.
化合物(1−1−1)を化合物(1−1−153)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.87Vで、初期輝度の90%以上の輝度を保持する時間は101時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-1-153). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 3.87 V, and the time for maintaining 90% or more of the initial luminance was 101 hours.
化合物(1−1−1)を化合物(1−1−172)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.79Vで、初期輝度の90%以上の輝度を保持する時間は87時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-1-172). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test starting voltage was 3.79 V, and the time for maintaining 90% or more of the initial luminance was 87 hours.
化合物(1−1−1)を化合物(1−1−191)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.57Vで、初期輝度の90%以上の輝度を保持する時間は203時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-1-191). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 3.57 V, and the time for maintaining 90% or more of the initial luminance was 203 hours.
化合物(1−1−1)を化合物(1−1−210)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.58Vで、初期輝度の90%以上の輝度を保持する時間は172時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-1-210). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 3.58 V, and the time for maintaining 90% or more of the initial luminance was 172 hours.
化合物(1−1−1)を化合物(1−1−229)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.67Vで、初期輝度の90%以上の輝度を保持する時間は80時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-1-229). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The drive test start voltage was 3.67 V, and the time for maintaining 90% or more of the initial brightness was 80 hours.
化合物(1−1−1)を化合物(1−2−1)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は4.20Vで、初期輝度の90%以上の輝度を保持する時間は57時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-2-1). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test starting voltage was 4.20 V, and the time for maintaining 90% or more of the initial luminance was 57 hours.
化合物(1−1−1)を化合物(1−2−153)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.85Vで、初期輝度の90%以上の輝度を保持する時間は62時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-2153). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 3.85 V, and the time for maintaining a luminance of 90% or more of the initial luminance was 62 hours.
化合物(1−1−1)を化合物(1−2−172)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は3.65Vで、初期輝度の90%以上の輝度を保持する時間は104時間だった。An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (1-2172). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 3.65 V, and the time for maintaining a luminance of 90% or more of the initial luminance was 104 hours.
<比較例2>
化合物(1−1−1)を化合物(F)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は5.35Vで、初期輝度の90%以上の輝度を保持する時間は2時間だった。<Comparative example 2>
An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (F). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 5.35 V, and the time for maintaining 90% or more of the initial luminance was 2 hours.
<比較例3>
化合物(1−1−1)を化合物(G)に替えた以外は実施例2に準じた方法で有機EL素子を得た。ITO電極を陽極、Liq/マグネシウム−銀合金電極を陰極として、初期輝度2000cd/m2を得るための電流密度により、定電流駆動試験を実施した。駆動試験開始電圧は4.20Vで、初期輝度の90%以上の輝度を保持する時間は30時間だった。<Comparative Example 3>
An organic EL device was obtained by the method according to Example 2 except that the compound (1-1-1) was changed to the compound (G). A constant current driving test was carried out using an ITO electrode as an anode and a Liq / magnesium-silver alloy electrode as a cathode at a current density for obtaining an initial luminance of 2000 cd / m 2 . The driving test start voltage was 4.20 V, and the time for maintaining the luminance of 90% or more of the initial luminance was 30 hours.
以上の結果を表4にまとめた。
本発明の好ましい態様によれば、特に発光素子の寿命を向上させ、駆動電圧とのバランスも優れた有機電界発光素子、それを備えた表示装置およびそれを備えた照明装置などを提供することができる。 According to a preferred aspect of the present invention, it is possible to provide an organic electroluminescent element that improves the lifetime of the light emitting element and has an excellent balance with the driving voltage, a display device including the organic electroluminescent element, and a lighting device including the organic electroluminescent element. it can.
Claims (11)
Pyはピリジルであり、このピリジルの任意の水素は炭素数1〜6のアルキル、炭素数3〜6のシクロアルキル、炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよいフェニル、炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよい1−ナフチル、または炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよい2−ナフチルで置き換えられていてもよく;
Rは水素、炭素数1〜6のアルキル、炭素数3〜6のシクロアルキルまたは炭素数6〜14のアリールであり、このアリールの任意の水素は炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置き換えられていてもよく;また、
式(1)で表される化合物における少なくとも1つの水素が重水素で置き換えられていてもよい。A compound represented by the following formula (1).
Py is pyridyl, and any hydrogen of the pyridyl is substituted with alkyl having 1 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 6 carbons. 1-naphthyl optionally substituted with phenyl, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, or alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms Optionally substituted with 2-naphthyl;
R is hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 14 carbon atoms, and any hydrogen in the aryl is alkyl having 1 to 6 carbon atoms or 3 to 3 carbon atoms. Optionally substituted with 6 cycloalkyl;
At least one hydrogen in the compound represented by the formula (1) may be replaced with deuterium.
Pyはピリジルであり、このピリジルの任意の水素は炭素数1〜6のアルキル、炭素数3〜6のシクロアルキル、炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよいフェニル、炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよい1−ナフチル、または炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置換されていてもよい2−ナフチルで置き換えられていてもよく;
Rは水素、炭素数1〜6のアルキル、炭素数3〜6のシクロアルキルまたは炭素数6〜14のアリールであり、このアリールの任意の水素は炭素数1〜6のアルキルまたは炭素数3〜6のシクロアルキルで置き換えられていてもよく;また、
式(1−1)または(1−2)で表される化合物における少なくとも1つの水素が重水素で置き換えられていてもよい。The compound of Claim 1 represented by a following formula (1-1) or (1-2).
Py is pyridyl, and any hydrogen of the pyridyl is substituted with alkyl having 1 to 6 carbons, cycloalkyl having 3 to 6 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 6 carbons. 1-naphthyl optionally substituted with phenyl, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms, or alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 6 carbon atoms Optionally substituted with 2-naphthyl;
R is hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 14 carbon atoms, and any hydrogen in the aryl is alkyl having 1 to 6 carbon atoms or 3 to 3 carbon atoms. Optionally substituted with 6 cycloalkyl;
At least one hydrogen in the compound represented by formula (1-1) or (1-2) may be replaced with deuterium.
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