JP2018100264A - 化合物およびそれを用いた有機電子デバイス - Google Patents
化合物およびそれを用いた有機電子デバイス Download PDFInfo
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- JP2018100264A JP2018100264A JP2017232424A JP2017232424A JP2018100264A JP 2018100264 A JP2018100264 A JP 2018100264A JP 2017232424 A JP2017232424 A JP 2017232424A JP 2017232424 A JP2017232424 A JP 2017232424A JP 2018100264 A JP2018100264 A JP 2018100264A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 101
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 125000004431 deuterium atom Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 6
- 125000005104 aryl silyl group Chemical group 0.000 claims description 6
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- KHNYNFUTFKJLDD-UHFFFAOYSA-N Benzo[j]fluoranthene Chemical group C1=CC(C=2C3=CC=CC=C3C=CC=22)=C3C2=CC=CC3=C1 KHNYNFUTFKJLDD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001454 anthracenes Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002219 fluoranthenes Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003220 pyrenes Chemical group 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical group O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 claims description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002987 phenanthrenes Chemical group 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 31
- 239000000543 intermediate Substances 0.000 description 121
- 239000010410 layer Substances 0.000 description 71
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000000434 field desorption mass spectrometry Methods 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 239000012265 solid product Substances 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 125000000524 functional group Chemical group 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 14
- 239000000376 reactant Substances 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000004048 modification Effects 0.000 description 8
- 238000012986 modification Methods 0.000 description 8
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- -1 4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl Chemical group 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 3
- RYMQWZPAZBQXMX-UHFFFAOYSA-N 2-bromodibenzo[1,3-e:1',2'-f][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC(Br)=CC=C21 RYMQWZPAZBQXMX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 150000001555 benzenes Chemical group 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 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 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- LNJZJDLDXQQJSG-UHFFFAOYSA-N 2-phenylpyrazine Chemical group C1=CC=CC=C1C1=CN=CC=N1 LNJZJDLDXQQJSG-UHFFFAOYSA-N 0.000 description 2
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical group C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 2
- XWSSUYOEOWLFEI-UHFFFAOYSA-N 3-phenylpyridazine Chemical group C1=CC=CC=C1C1=CC=CN=N1 XWSSUYOEOWLFEI-UHFFFAOYSA-N 0.000 description 2
- SKKKJNPBIGQNEJ-UHFFFAOYSA-N 9h-fluorene-1,9-diamine Chemical compound C1=CC(N)=C2C(N)C3=CC=CC=C3C2=C1 SKKKJNPBIGQNEJ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- NDMVXIYCFFFPLE-UHFFFAOYSA-N anthracene-9,10-diamine Chemical compound C1=CC=C2C(N)=C(C=CC=C3)C3=C(N)C2=C1 NDMVXIYCFFFPLE-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 150000002220 fluorenes Chemical group 0.000 description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002790 naphthalenes Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- VRAMIWXXKJVLIG-UHFFFAOYSA-N 3-[3-[10-(3-pyridin-3-ylphenyl)anthracen-9-yl]phenyl]pyridine Chemical compound N1=CC(=CC=C1)C=1C=C(C=CC=1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC(=CC=C1)C=1C=NC=CC=1 VRAMIWXXKJVLIG-UHFFFAOYSA-N 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- WCXKTQVEKDHQIY-UHFFFAOYSA-N 3-[3-[3-(3,5-dipyridin-3-ylphenyl)phenyl]-5-pyridin-3-ylphenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=NC=CC=2)=C1 WCXKTQVEKDHQIY-UHFFFAOYSA-N 0.000 description 1
- RWHRJJMRDNZTHU-UHFFFAOYSA-N 4-N-naphthalen-1-yl-4-N-[4-[4-[1-(naphthalen-1-ylamino)-4-(N-phenylanilino)cyclohexa-2,4-dien-1-yl]phenyl]phenyl]-1-N,1-N-diphenylbenzene-1,4-diamine Chemical compound C1(=CC=C(C=C1)C1(CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)NC1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)N(C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 RWHRJJMRDNZTHU-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 1
- RUQICFLRSLDXDP-UHFFFAOYSA-N 9-naphthalen-2-yl-10-(4-naphthalen-1-ylphenyl)anthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=2C3=CC=CC=C3C=CC=2)C=C1 RUQICFLRSLDXDP-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- VYVIOMJSKUGJLV-UHFFFAOYSA-N [Ir+2] Chemical compound [Ir+2] VYVIOMJSKUGJLV-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-N aluminum;quinolin-8-ol Chemical compound [Al+3].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical group C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004147 desorption mass spectrometry Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 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
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ABCGFHPGHXSVKI-UHFFFAOYSA-O meso-tetrakis(n-methyl-4-pyridyl)porphine(4+) Chemical compound C1=C[N+](C)=CC=C1C(C1=CC=C(N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(=N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(N1)=C1C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 ABCGFHPGHXSVKI-UHFFFAOYSA-O 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000000075 oxide glass Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical compound C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
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- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
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- 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
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- 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
- C07D213/22—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 two or more pyridine rings directly linked together, e.g. bipyridyl
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- 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
- C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
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- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
Description
第1の電極上に形成された正孔注入層;
正孔注入層上に形成された正孔輸送層;
正孔輸送層上に形成された発光層;
発光層上に形成された電子輸送層;
電子輸送層と第2の電極との間に形成された電子注入層。
新規化合物の調製に用いた中間体A1は以下の工程により合成した。中間体A1の合成経路をスキームA1に要約した。
四塩化炭素(CCl4)(出発材料の5倍)中の3−ブロモジベンゾ[a,d]シクロヘプテン−5−オン(86g、1.0当量)、N−ブロモスクシンイミド(NBS)(106g、2当量)、ベンジルペルオキシド(0.7g、0.01当量)の混合物を85℃に加熱した。反応の進行を高速液体クロマトグラフィ(HPLC)でモニターした。反応完了後、沈殿物を濾過により分離し、CH3OHで洗浄し、これを次いで再結晶で精製した。精製された生成物を濃縮乾固すると、白色の固体生成物が123gの量および収率92.3%で得られた。
得られた中間体A1−1(116.0g、1.0当量)およびフラン(1.5当量)をTHF(1.0M)に溶解し、反応物を0℃に冷却し、次いでカリウムtert−ブトキシド(K−OtBu)(87.8g、3.0当量)で処理した。反応物を0℃で1時間撹拌し、次いで室温でさらに12時間撹拌した。反応の完了後、DI水で反応をクエンチし、有機層を溶媒抽出操作によって回収し、硫酸ナトリウムで乾燥させた。有機層から溶媒を減圧下の蒸留により除去し、得られた残渣をシリカゲルカラムクロマトグラフィで精製した。精製した生成物を濃縮乾固して、淡黄色の固体生成物を収率60.3%で得た。
酢酸エチル(EA、2.0M)中の中間体A1−2(1.0当量)および5%Pd/C(0.025当量)の懸濁液を、水素バルーンによって提供される水素雰囲気(H2)下で3時間〜6時間撹拌した。得られた混合物をセライトのパッドで濾過し、EAで洗浄し、濾液を減圧下で濃縮して、黄色固体生成物100g(100%)を得た。
トルエン530ml中の中間体A1−3(53g、1.0当量)およびp−トルエンスルホン酸(PTSA)(2.0当量)を12時間加熱還流した。反応混合物を室温に冷却し、次いでNaHCO3の飽和水溶液でクエンチし、CH2Cl2で抽出した。有機層を水、ブライン(塩水)で洗浄し、続いて無水Na2SO4で乾燥させた。次に、得られた溶液を減圧下で濃縮し、溶離液としてCH2Cl2/ヘキサン1/1(v/v)を用いるシリカゲルカラムクロマトグラフィにより精製して、淡黄色の固体生成物を46.0gの量および91.5%の収率で得た。
新規化合物を調製するために使用される中間体A2は、出発材料3−ブロモジベンゾ[a,d]シクロヘプテン−5−オンを2−ブロモジベンゾ[a,d]シクロヘプテン−5−オン(CAS番号198707−82−3)に置き換えた以外は、工程1〜4を通して中間体A1と同様の方法で合成した。中間体A2の合成経路をスキームA2に要約した。すべての中間体を上記の方法に従って分析し、その結果を表1に列挙した。
新規化合物を調製するために使用される中間体A3は、出発材料3−ブロモジベンゾ[a,d]シクロヘプテン−5−オンを3,7−ジブロモジベンゾ[a,d]シクロヘプテン−5−オン(CAS番号226946−20−9)に置き換えた以外は、工程1〜4を通して中間体A1と同様の方法で合成した。中間体A3の合成経路をスキームA3に要約した。すべての中間体を上記のように分析し、その結果を表1に列挙した。
中間体A1〜A3に加えて、当業者は他の出発材料を採用し、スキームA1〜A3と同様の反応機構により他の所望の中間体を首尾よく合成することができる。中間体A1〜A3の適用可能な変更は、例えば、以下の中間体A4〜A15であってもよいが、これらに限定されない。
1−ブロモ−2−ヨードベンゼンおよびヘテロアリールボロン酸(反応体An)を反応させることにより中間体B1〜B6を合成した。中間体Bnの一般的な合成経路をスキームBに要約した。以下のスキームBにおいて、「反応体An」は、表2に列挙される反応体A1〜A6のいずれか1つなどであってもよく、「中間体Bn」は、中間体B1〜B6のいずれか1つであってもよい。
中間体B1〜B6に加えて、当業者は、1−ブロモ−2−ヨードベンゼン以外の任意のジハロベンゼンおよび反応体A1〜A6以外の任意のヘテロアリールボロン酸を採用して、スキームBと同様の反応機構を介して他の所望の中間体Bnを首尾良く合成することができる。中間体B1〜B6の適用可能な変更は、例えば以下のような中間体B7およびB8であってもよいが、これらに限定されない。
上述の中間体B1〜B8、特に中間体B1〜B6をさらに採用して中間体Cnを合成することができた。中間体Cnの一般的な合成経路をスキームC1に要約した。以下のスキームC1において、「中間体An」は、上述の中間体A1〜A15などのいずれか1つであってもよく、「中間体Bn」は、上述の中間体B1〜B8などのいずれか1つであってもよく、「中間体Cn」は、表3−1に記載の中間体C1〜C9などのいずれか1つであってもよい。中間体C1〜C9はそれぞれ以下の工程で合成した。
中間体Bn(1.0当量)を120mLの無水THF(0.4M)に溶解し、−78℃に冷却した。n−ブチルリチウム(n−BuLi)(2.5M,1.0当量)を上記冷却溶液にゆっくり加え、反応塊を1時間撹拌した。1時間撹拌した後、中間体An(0.7当量)を反応溶液に添加し、室温でさらに3時間攪拌した。反応完了後、飽和塩化アンモニウム溶液で反応をクエンチし、有機溶媒で抽出した。有機層を分離し、濃縮し、石油エーテルで再結晶して白色固体生成物を得た。
アルコール中間体(1.0当量)、酢酸(反応体に対してw/v=1/3)およびH2SO4(5滴)を混合し、混合物を110℃で6時間撹拌した。次いで、溶媒を減圧下で除去し、残渣をカラムクロマトグラフィで精製した。残留塊をトルエンで再結晶して白色固体生成物を得た。
中間体C1〜C9に加えて、当業者は、中間体A1〜A3以外の任意の中間体Anおよび/または中間体B1〜B6以外の任意の中間体Bnを採用して、スキームC1と同様の反応機構により他の所望の中間体Cnを首尾よく合成できる。中間体C1〜C9の適用可能な変更は、例えば、以下の中間体C10〜C33であってもよいが、これに限定されない。
中間体C34およびC35に加えて、当業者は、中間体C8、C9、C22〜C33などのチオフラン基を含む他の中間体Cnを採用して、スキームC2またはスキームC3と同様の反応機構によって他の所望の中間体Cnを合成することができる。中間体C34およびC35の適用可能な変更は、例えば、以下の中間体C36〜C46であり得るが、これらに限定されない。
上述の中間体Cnは、宮浦(Miyaura)ホウ素化反応を介して中間体Cn−Bにさらに変更することができた。「中間体Cn−B」は、そのブロモ基が(ピナコラト)ボロン基で置き換えられた中間体Cnから誘導された化合物を対象とした。中間体Cn−Bの合成経路をスキームC1−Bに要約した。中間体Cn−Bを以下の工程により合成した。
中間体Cn−Bに加えて、当業者は、上述の中間体Cnのいずれか1つを採用して宮浦ホウ素化反応を行い、以下のような他の所望の中間体Cn−Bを首尾良く合成することができる。
上述の中間体CnおよびCn−Bのそれぞれを種々の反応体と反応させて、種々の特許請求された新規化合物を合成することができた。特許請求された新規化合物の一般的な合成経路をスキームIに要約した。以下のスキームIにおいて、「反応体B」は表4に列挙された反応体B1〜B34のいずれか1つであってもよく、「中間体C」は上述の中間体CnおよびCn−Bなどのいずれか1つであってもよい。化合物はそれぞれ以下の工程で合成した。
化合物I〜XXVIIに加えて、当業者は、スキームIと同様の反応機構を介して、任意の中間体C、すなわち上述の中間体CnまたはCn−Bを任意の反応体Bnと反応させて、他の所望の特許請求された新規化合物を合成することができる。
ITO層を1500Åの厚さでコーティングしたガラス基板(ITO基板と略記)を、洗浄剤を溶解した蒸留水に入れ、超音波洗浄した。洗浄剤はFischer Co.の製品であり、蒸留水はフィルタ(Millipore Co.)で2回濾過した蒸留水であった。ITO層を30分間洗浄した後、蒸留水で2回10分間超音波洗浄した。洗浄終了後、ガラス基板をイソプロピルアルコール、アセトン、メタノール溶媒で超音波洗浄し、次いで乾燥させた後、プラズマ清浄装置に搬送した。次いで、基板を酸素プラズマで5分間清浄し、次いで真空蒸発器に移した。
赤色OLEDデバイスを調製するために、複数の有機層をそれぞれ、表7に列挙されるような順序に従ってITO基板上に堆積させ、赤色OLEDデバイスの有機層の材料および厚さもまた表7に列挙した。
緑色OLEDデバイスを調製するために、複数の有機層をそれぞれ、表8に列挙されるような順序に従ってITO基板上に堆積させ、緑色OLEDデバイスの有機層の材料および厚さもまた表8に列挙した。
表8:緑色OLEDデバイスにおける層のコーティング順序、材料および厚さ。
青色OLEDデバイスを調製するために、複数の有機層をそれぞれ、表9に列挙されるような順序に従ってITO基板上に堆積させ、青色OLEDデバイスの有機層の材料および厚さもまた表9に列挙した。
OLEDデバイスの性能を評価するために、赤色、緑色および青色OLEDデバイスを、光度計としてのPR650および電源としてのKeithley 2400によって測定した。色座標(x,y)は、CIE色度スケール(Commission Internationale de L’Eclairage、1931)に従って決定した。結果を表10に示した。青色および赤色OLEDデバイスについては、データを1000nitで収集した。緑色OLEDデバイスについては、データを3000nitで収集した。
Claims (8)
- 下記式(I)で表される化合物:
式中、X1およびX2はそれぞれ独立してC(Ra)であり、前記2つの(Ra)は同じであるかまたは異なり、前記2つの(Ra)は共に連結してアリール環を形成し;
式中、X3およびX4はそれぞれ独立してC(Rb)であり、前記2つの(Rb)は同じであるかまたは異なり、前記2つの(Rb)は共に連結して少なくとも1つのフラン基、少なくとも1つのチオフェン基または少なくとも1つのチオフェンS,S−ジオキシド基を含むヘテロアリール環を形成し;
式中、Z1〜Z12は、それぞれ独立して、水素原子、重水素原子、トリフルオロメチル基、ハロゲン基、シアノ基、ニトロ基、1〜40個の炭素原子を有するアルキル基、2〜40個の炭素原子を有するアルケニル基、2〜40個の炭素原子を有するアルキニル基、3〜60個の環炭素原子を有するシクロアルキル基、3〜60個の環炭素原子を有するヘテロシクロアルキル基、6〜60個の環炭素原子を有するアリール基、3〜60個の環炭素原子を有するヘテロアリール基、1〜40個の炭素原子を有するアルコキシ基、6〜60個の環炭素原子を有するアリールオキシ基、1〜40個の炭素原子を有するアルキルシリル基、6〜60個の環炭素原子を有するアリールシリル基、1〜40個の炭素原子を有するアルキルボロン基、6〜60個の環炭素原子を有するアリールボロン基、1〜40個の炭素原子を有するホスフィン基、および1〜40個の炭素原子を有するホスフィンオキシド基からなる群から選択される。 - 下記式(I−I)〜(I−XVIII)で表される、請求項1に記載の化合物:
- 前記ヘテロアリール環に含まれる前記芳香族構造は、置換または無置換ベンゼン構造、置換または無置換ナフタレン構造、置換または無置換アントラセン構造、置換または無置換フェナントレン構造、置換または無置換フルオレン構造、置換または無置換ピレン構造、置換または無置換ベンゾフェナントレン構造、置換または無置換ベンゾピレン構造、置換または無置換フルオランテン構造、および置換または無置換ベンゾフルオランテン構造からなる群から選択される、請求項2に記載の化合物。
- X1およびX2から伸びた前記アリール環は、置換または無置換ベンゼン環、置換または無置換ナフタレン環、置換または無置換アントラセン環、置換または無置換フェナントレン環、置換または無置換フルオレン環、置換または無置換ピレン環、置換または無置換ベンゾフェナントレン環、置換または無置換ベンゾピレン環、置換または無置換フルオランテン環、および置換または無置換ベンゾフルオランテン環からなる群から選択される、請求項1から3のいずれか一項に記載の化合物。
- Z1〜Z8の少なくとも1つは、以下からなる群から選択される、請求項1から4のいずれか一項に記載の化合物:
式中、nは0〜4の正の整数であり、mは0〜3の正の整数であり、oは0〜3の正の整数であり、mとoとの合計は5以下である。 - Z2、Z3、Z6およびZ7の少なくとも1つは、以下からなる群から選択される、請求項1から4のいずれか一項に記載の化合物。
- 前記化合物は、以下からなる群から選択される、請求項1に記載の化合物。
- 第1の電極と、第2の電極と、前記第1の電極と前記第2の電極との間に配置された有機層とを含み、前記有機層は請求項1から7のいずれか一項に記載の化合物を含む有機電子デバイス。
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