JP5262192B2 - 電子輸送材料およびこれを用いた有機電界発光素子 - Google Patents
電子輸送材料およびこれを用いた有機電界発光素子 Download PDFInfo
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- JP5262192B2 JP5262192B2 JP2008053379A JP2008053379A JP5262192B2 JP 5262192 B2 JP5262192 B2 JP 5262192B2 JP 2008053379 A JP2008053379 A JP 2008053379A JP 2008053379 A JP2008053379 A JP 2008053379A JP 5262192 B2 JP5262192 B2 JP 5262192B2
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- Prior art keywords
- biphenylyl
- formula
- naphthyl
- group
- compound
- Prior art date
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- 239000000463 material Substances 0.000 title abstract description 45
- 150000001875 compounds Chemical class 0.000 claims abstract description 195
- YTEIHWVCQJZNEN-UHFFFAOYSA-N 3-pyridin-4-ylpyridine Chemical group C1=CN=CC(C=2C=CN=CC=2)=C1 YTEIHWVCQJZNEN-UHFFFAOYSA-N 0.000 claims abstract description 34
- -1 2-biphenylyl Chemical group 0.000 claims description 105
- 239000001257 hydrogen Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 26
- 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 description 24
- 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 description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims 10
- 238000010168 coupling process Methods 0.000 claims 10
- 125000005647 linker group Chemical group 0.000 abstract description 68
- 230000009467 reduction Effects 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 93
- 239000010410 layer Substances 0.000 description 69
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000003786 synthesis reaction Methods 0.000 description 36
- 238000007740 vapor deposition Methods 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 34
- 239000000243 solution Substances 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
- 238000000034 method Methods 0.000 description 20
- 239000012141 concentrate Substances 0.000 description 19
- 238000010438 heat treatment Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- 239000010408 film Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- 239000012300 argon atmosphere Substances 0.000 description 13
- 238000000151 deposition Methods 0.000 description 13
- 230000008021 deposition Effects 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- 229910052750 molybdenum Inorganic materials 0.000 description 11
- 239000011733 molybdenum Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 10
- 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 9
- ZKNBQZBRNLAVHS-UHFFFAOYSA-N 3-bromo-5-pyridin-4-ylpyridine Chemical compound BrC1=CN=CC(C=2C=CN=CC=2)=C1 ZKNBQZBRNLAVHS-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 9
- 239000010409 thin film Substances 0.000 description 8
- 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 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000003054 catalyst Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000001963 growth medium Substances 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 235000011056 potassium acetate Nutrition 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 5
- 235000019798 tripotassium phosphate Nutrition 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000006411 Negishi coupling reaction Methods 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- 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 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 0 *C1(*)c2cc(-c3ncc(-c4cncc(-c5ccncc5)c4)[n]3-c3ccccc3)ccc2-c2ccc(C(NC=C3c4cc(-c5ccncc5)cnc4)N3c3ccccc3)cc12 Chemical compound *C1(*)c2cc(-c3ncc(-c4cncc(-c5ccncc5)c4)[n]3-c3ccccc3)ccc2-c2ccc(C(NC=C3c4cc(-c5ccncc5)cnc4)N3c3ccccc3)cc12 0.000 description 3
- GPOMKCKAJSZACG-UHFFFAOYSA-N 2-phenylanthracene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2C(C=CC=C2)=C2)C2=C1 GPOMKCKAJSZACG-UHFFFAOYSA-N 0.000 description 3
- RQHQTFLXMUBQBU-UHFFFAOYSA-N 3,6-dibromo-9-naphthalen-1-ylcarbazole Chemical compound C12=CC=C(Br)C=C2C2=CC(Br)=CC=C2N1C1=CC=CC2=CC=CC=C12 RQHQTFLXMUBQBU-UHFFFAOYSA-N 0.000 description 3
- PGKQJNOISHJIBI-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)triphenylen-2-yl]-1,3,2-dioxaborolane Chemical group O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2C(=CC(=CC=2)B2OC(C)(C)C(C)(C)O2)C=2C3=CC=CC=2)C3=C1 PGKQJNOISHJIBI-UHFFFAOYSA-N 0.000 description 3
- JBYBLHYEVCYGME-UHFFFAOYSA-N 9,10-dibromo-2-phenylanthracene Chemical compound C=1C=C2C(Br)=C3C=CC=CC3=C(Br)C2=CC=1C1=CC=CC=C1 JBYBLHYEVCYGME-UHFFFAOYSA-N 0.000 description 3
- BLKLIQJTGNDTOL-UHFFFAOYSA-N 9-phenyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C2C3=CC=C(B4OC(C)(C)C(C)(C)O4)C=C3N(C=3C=CC=CC=3)C2=C1 BLKLIQJTGNDTOL-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- FSSKYZQJNSHRLG-UHFFFAOYSA-N C1=CC=C(C=C1)N2C3=C(C=CC(=C3)OS(=O)(=O)C(F)(F)F)C4=C2C=C(C=C4)OS(=O)(=O)C(F)(F)F Chemical compound C1=CC=C(C=C1)N2C3=C(C=CC(=C3)OS(=O)(=O)C(F)(F)F)C4=C2C=C(C=C4)OS(=O)(=O)C(F)(F)F FSSKYZQJNSHRLG-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 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
- VVSCYVPRHRQDPS-UHFFFAOYSA-N [7-(trifluoromethylsulfonyloxy)triphenylen-2-yl] trifluoromethanesulfonate Chemical group C1=CC=C2C3=CC(OS(=O)(=O)C(F)(F)F)=CC=C3C3=CC=C(OS(=O)(=O)C(F)(F)F)C=C3C2=C1 VVSCYVPRHRQDPS-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YXDSQNPTLSHISU-UHFFFAOYSA-N triphenylene-2,7-diol Chemical group C1=CC=C2C3=CC(O)=CC=C3C3=CC=C(O)C=C3C2=C1 YXDSQNPTLSHISU-UHFFFAOYSA-N 0.000 description 3
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- MDILQAKUYPNNON-UHFFFAOYSA-N 2,7-dimethoxytriphenylene Chemical group C1=CC=C2C3=CC(OC)=CC=C3C3=CC=C(OC)C=C3C2=C1 MDILQAKUYPNNON-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- FIHILUSWISKVSR-UHFFFAOYSA-N 3,6-dibromo-9h-carbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3NC2=C1 FIHILUSWISKVSR-UHFFFAOYSA-N 0.000 description 2
- NUUYTGXGPHSYQZ-UHFFFAOYSA-N 3-[2-phenyl-10-(5-pyridin-4-ylpyridin-3-yl)anthracen-9-yl]-5-pyridin-4-ylpyridine Chemical compound C1=CC=CC=C1C1=CC=C(C(C=2C=C(C=NC=2)C=2C=CN=CC=2)=C2C(C=CC=C2)=C2C=3C=C(C=NC=3)C=3C=CN=CC=3)C2=C1 NUUYTGXGPHSYQZ-UHFFFAOYSA-N 0.000 description 2
- UQVQCERBEPZNSK-UHFFFAOYSA-N 3-pyridin-4-yl-5-[7-(5-pyridin-4-ylpyridin-3-yl)triphenylen-2-yl]pyridine Chemical group C1=CC2=C(C=C1)C1=C(C=CC(=C1)C1=CN=CC(=C1)C1=CC=NC=C1)C1=C2C=C(C=C1)C1=CC(=CN=C1)C1=CC=NC=C1 UQVQCERBEPZNSK-UHFFFAOYSA-N 0.000 description 2
- HNILOESMUPGLRZ-UHFFFAOYSA-N 9-naphthalen-1-yl-3,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N(C=2C3=CC=CC=C3C=CC=2)C=2C3=CC(=CC=2)B2OC(C)(C)C(C)(C)O2)C3=C1 HNILOESMUPGLRZ-UHFFFAOYSA-N 0.000 description 2
- AIVVGIAPEHWVGF-UHFFFAOYSA-N 9-phenyl-2,7-bis(5-pyridin-4-ylpyridin-3-yl)carbazole Chemical compound C1=CC=C(C=C1)N1C2=C(C=CC(=C2)C2=CC(=CN=C2)C2=CC=NC=C2)C2=C1C=C(C=C2)C1=CN=CC(=C1)C1=CC=NC=C1 AIVVGIAPEHWVGF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- JPQDHQFEQPKVIP-UHFFFAOYSA-N C1=CC=C2C(=C1)C(=CC=C2C3=CN=CC(=C3)C4=CC=NC=C4)C5=CN=CC(=C5)C6=CC=NC=C6 Chemical compound C1=CC=C2C(=C1)C(=CC=C2C3=CN=CC(=C3)C4=CC=NC=C4)C5=CN=CC(=C5)C6=CC=NC=C6 JPQDHQFEQPKVIP-UHFFFAOYSA-N 0.000 description 2
- CZHQFSUIUUBAPE-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=CC=CC=C3C24C5=C(C=CC(=C5)C6=CN=CC(=C6)C7=CC=NC=C7)C8=C4C=C(C=C8)C9=CN=CC(=C9)C1=CC=NC=C1 Chemical compound C1=CC=C2C(=C1)C3=CC=CC=C3C24C5=C(C=CC(=C5)C6=CN=CC(=C6)C7=CC=NC=C7)C8=C4C=C(C=C8)C9=CN=CC(=C9)C1=CC=NC=C1 CZHQFSUIUUBAPE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 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
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electroluminescent Light Sources (AREA)
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| JPH1144632A (ja) * | 1997-07-28 | 1999-02-16 | Toa Medical Electronics Co Ltd | 粒子計測装置のデータ異常判定方法 |
| CN101808964B (zh) | 2007-08-08 | 2014-01-01 | 通用显示公司 | 在磷光性发光二极管中的单苯并[9，10]菲生色团 |
| EP2123733B1 (en) * | 2008-05-13 | 2013-07-24 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, display device and lighting device |
| JP5493333B2 (ja) * | 2008-11-05 | 2014-05-14 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、白色有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| US8486544B2 (en) | 2009-08-28 | 2013-07-16 | Industrial Technology Research Institute | Quinoxaline derivatives and organic light-emitting diodes comprising the same |
| TWI402259B (zh) | 2009-08-28 | 2013-07-21 | Ind Tech Res Inst | 喹啉衍生物及包含此喹啉衍生物之有機發光二極體 |
| DE102009053382A1 (de) | 2009-11-14 | 2011-05-19 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
| TWI491602B (zh) | 2009-12-03 | 2015-07-11 | Jnc Corp | 具有含吡啶取代基的苯并［ｃ］咔唑化合物及有機電激發光元件 |
| WO2011152466A1 (ja) * | 2010-06-02 | 2011-12-08 | Jnc株式会社 | 電子受容性窒素含有へテロアリールを含む置換基を有するカルバゾール化合物および有機電界発光素子 |
| JP5799772B2 (ja) * | 2010-11-25 | 2015-10-28 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
| WO2012073541A1 (ja) * | 2010-12-03 | 2012-06-07 | Jnc株式会社 | ピリジンを含む置換基を有するベンゾ［ｃ］カルバゾール化合物および有機電界発光素子 |
| CN102532105A (zh) * | 2010-12-17 | 2012-07-04 | 清华大学 | 一种含有吡啶基团的三亚苯类化合物及其应用 |
| JP5453621B2 (ja) * | 2011-02-23 | 2014-03-26 | 保土谷化学工業株式会社 | 置換されたトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
| JP5807601B2 (ja) * | 2011-04-01 | 2015-11-10 | Jnc株式会社 | アントラセン誘導体およびこれを用いた有機電界発光素子 |
| WO2013128818A1 (ja) * | 2012-02-28 | 2013-09-06 | 保土谷化学工業株式会社 | 置換基を有するピリジル基とトリフェニレン環構造を有する化合物および有機エレクトロルミネッセンス素子 |
| JP5641068B2 (ja) * | 2013-01-24 | 2014-12-17 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子 |
| CN107602355A (zh) * | 2017-09-16 | 2018-01-19 | 浙江工业大学 | 一种苯并菲双硼酸酯关键中间体关键中间体的制备方法 |
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| DE19628719B4 (de) * | 1996-07-17 | 2006-10-05 | Hans-Werner Prof. Dr. Schmidt | Elektronenleitende Schicht in organischen, elektrolumineszierenden Anordnungen |
| DE60100187T2 (de) * | 2000-09-07 | 2004-04-01 | Chisso Corp. | Organische Elektrolumineszenzanordung mit einem Dipyridylthiophenderivat |
| JP4172172B2 (ja) * | 2001-10-10 | 2008-10-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
| JP2006013226A (ja) * | 2004-06-28 | 2006-01-12 | Stanley Electric Co Ltd | 有機ｌｅｄ素子 |
| JP2006176491A (ja) * | 2004-11-25 | 2006-07-06 | Kyoto Univ | ピレン系化合物及びこれを用いた発光トランジスタ素子 |
| US20060186797A1 (en) * | 2005-02-15 | 2006-08-24 | Tosoh Corporation | Pi-conjugated compound having cardo structure, process for preparing same and use of same |
| WO2007023840A1 (ja) * | 2005-08-26 | 2007-03-01 | Tosoh Corporation | １，３，５－トリアジン誘導体、その製造方法、およびこれを構成成分とする有機電界発光素子 |
| JP2008120696A (ja) * | 2006-11-08 | 2008-05-29 | Chemiprokasei Kaisha Ltd | 新規なトリピリジルフェニル誘導体、それよりなる電子輸送材料およびそれを含む有機エレクトロルミネッセンス素子 |
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