JP5583349B2 - 新規なアントラセン誘導体およびこれを用いた有機電子素子 - Google Patents
新規なアントラセン誘導体およびこれを用いた有機電子素子 Download PDFInfo
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- JP5583349B2 JP5583349B2 JP2008558191A JP2008558191A JP5583349B2 JP 5583349 B2 JP5583349 B2 JP 5583349B2 JP 2008558191 A JP2008558191 A JP 2008558191A JP 2008558191 A JP2008558191 A JP 2008558191A JP 5583349 B2 JP5583349 B2 JP 5583349B2
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- 150000001454 anthracenes Chemical class 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 181
- 239000010410 layer Substances 0.000 claims description 114
- 239000000126 substance Substances 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 238000002347 injection Methods 0.000 claims description 37
- 239000007924 injection Substances 0.000 claims description 37
- 239000011368 organic material Substances 0.000 claims description 23
- 230000005525 hole transport Effects 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 49
- 239000000463 material Substances 0.000 description 47
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 38
- 125000001072 heteroaryl group Chemical group 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 125000003342 alkenyl group Chemical group 0.000 description 27
- 125000000217 alkyl group Chemical group 0.000 description 26
- 125000003545 alkoxy group Chemical group 0.000 description 25
- 230000032258 transport Effects 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- -1 stilbenyl group Chemical group 0.000 description 22
- 125000000753 cycloalkyl group Chemical group 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
- 125000003277 amino group Chemical group 0.000 description 19
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 17
- 150000002367 halogens Chemical class 0.000 description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000002560 nitrile group Chemical group 0.000 description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 16
- 238000003756 stirring Methods 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000001769 aryl amino group Chemical group 0.000 description 10
- 230000005684 electric field Effects 0.000 description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000000151 deposition Methods 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 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 5
- 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 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 150000004056 anthraquinones Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 0 *N(CC1=CC=CC=C=C1)C1=C*C=CC=C1 Chemical compound *N(CC1=CC=CC=C=C1)C1=C*C=CC=C1 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 3
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-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
- 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- HJBGZJMKTOMQRR-UHFFFAOYSA-N (3-formylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C=O)=C1 HJBGZJMKTOMQRR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PVVUJMPJDPJDSE-UHFFFAOYSA-N [CH-]1C=CC=C1.C1=CC=C[C-]1P(C1=CC=CC=C1)C1=CC=CC=C1.Cl.[Fe+2] Chemical compound [CH-]1C=CC=C1.C1=CC=C[C-]1P(C1=CC=CC=C1)C1=CC=CC=C1.Cl.[Fe+2] PVVUJMPJDPJDSE-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 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 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane 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-K 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PQJBRBDKANKHSC-UHFFFAOYSA-N (6-formylnaphthalen-2-yl)boronic acid Chemical compound C1=C(C=O)C=CC2=CC(B(O)O)=CC=C21 PQJBRBDKANKHSC-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- NTYDMFCZXBCEJY-UHFFFAOYSA-N 1-methyl-2-phenylcyclohexa-2,4-dien-1-amine Chemical group CC1(N)CC=CC=C1C1=CC=CC=C1 NTYDMFCZXBCEJY-UHFFFAOYSA-N 0.000 description 1
- LMXOZFCNVIVYSH-UHFFFAOYSA-N 2-bromo-9,10-dinaphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=C(C=4C5=CC=CC=C5C=CC=4)C4=CC=C(C=C43)Br)=CC=CC2=C1 LMXOZFCNVIVYSH-UHFFFAOYSA-N 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 1
- WSNKEJIFARPOSQ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(1-benzothiophen-2-ylmethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC3=C(S2)C=CC=C3)C=CC=1 WSNKEJIFARPOSQ-UHFFFAOYSA-N 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical group CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- MQFYUZCANYLWEI-UHFFFAOYSA-N 4-methylnaphthalen-1-amine Chemical group C1=CC=C2C(C)=CC=C(N)C2=C1 MQFYUZCANYLWEI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- RQOBAANEEZDSQZ-OZMFRADFSA-N B/C(/CNC=[IH])=C/C=C/C=C/C1=NNC([C@@H]2C=C[C@H](C)CC2)N1 Chemical compound B/C(/CNC=[IH])=C/C=C/C=C/C1=NNC([C@@H]2C=C[C@H](C)CC2)N1 RQOBAANEEZDSQZ-OZMFRADFSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YOGHVWRXEXKDSO-QXQQVEOESA-N C/C=C(\C1=C/[I]=C)/C(c2cc(cccc3)c3cc2)=C(C=C(C=C2)c3c(cccc4)c4c(-c(cc4)cc(cc5)c4cc5-c4nnc(-c5ccccc5)[n]4-c4ccccc4)c4c3cccc4)C2=C1c1cc2ccccc2cc1 Chemical compound C/C=C(\C1=C/[I]=C)/C(c2cc(cccc3)c3cc2)=C(C=C(C=C2)c3c(cccc4)c4c(-c(cc4)cc(cc5)c4cc5-c4nnc(-c5ccccc5)[n]4-c4ccccc4)c4c3cccc4)C2=C1c1cc2ccccc2cc1 YOGHVWRXEXKDSO-QXQQVEOESA-N 0.000 description 1
- WKYLIDZRAXMJMG-MFLXHLSASA-N CCCC[C@H](C1)NC(C(CC2)CCC2[C@@H](C)C23C(CBr)=CC=CC2C3)N1C1CCCCC1 Chemical compound CCCC[C@H](C1)NC(C(CC2)CCC2[C@@H](C)C23C(CBr)=CC=CC2C3)N1C1CCCCC1 WKYLIDZRAXMJMG-MFLXHLSASA-N 0.000 description 1
- PXXNWOVSHQUUHQ-UHFFFAOYSA-N C[IH]c1ccccc1 Chemical compound C[IH]c1ccccc1 PXXNWOVSHQUUHQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 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 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
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- 229920000123 polythiophene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound 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
- 238000007650 screen-printing Methods 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ACUGTEHQOFWBES-UHFFFAOYSA-M sodium hypophosphite monohydrate Chemical compound O.[Na+].[O-]P=O ACUGTEHQOFWBES-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/573—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with three six-membered rings
- C07C13/58—Completely or partially hydrogenated anthracenes
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
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- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
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- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
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- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/60—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing three rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
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- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- 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
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- 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
- C07D213/22—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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- 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
- C07D213/24—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
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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Description
R1およびR2は、互いに同じであるか相異し、独立してハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアリール基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC5〜C40のヘテロアリール基;およびハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアミノ基からなる群から選択され、
R3およびR4のうち少なくとも一つは下記化学式2の基であり、
R5およびR6は、互いに同じであるか相異し、水素;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC1〜C40のアルキル基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC3〜C40のシクロアルキル基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC3〜C40のアルケニル基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC3〜C40のアルコキシ基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC3〜C40のアミノ基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアリール基;およびハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC5〜C40のヘテロアリール基からなる群から選択されたり、隣接する基と脂肪族、芳香族、ヘテロ脂肪族、またはヘテロ芳香族の縮合環を形成したり、スピロ結合をしたりすることができ、
L1は直接結合であるか;C6〜C40のアリール基およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC2〜C40のアルケニレン基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアリーレン基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC5〜C40のヘテロアリーレン基;およびC1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアリールアミノ基からなる群から選択され、
Ar1は、C1〜C40のアルキル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、C5〜C40のヘテロアリール基、およびC6〜C40のアリールアミノ基からなる群から選択された一つ以上の基で置換または非置換されたC2〜C40のアルケニル基;C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、C5〜C40のヘテロアリール基、置換されたC2〜C40のアルケニレン基、およびC6〜C40のアリールアミノ基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアリール基;またはC1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、C5〜C40のヘテロアリール基、およびC6〜C40のアリールアミノ基からなる群から選択された一つ以上の基で置換または非置換されたC5〜C40のヘテロアリール基;およびC1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、C5〜C40のヘテロアリール基、およびC6〜C40のアリールアミノ基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアリールアミノ基からなる群から選択され、
R3およびR4のうち前記化学式2の基ではない基は、水素;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC1〜C40のアルキル基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC3〜C40のシクロアルキル基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアリール基;ハロゲン、アミノ基、ニトリル基、ニトロ基、C1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC5〜C40のヘテロアリール基;およびC1〜C40のアルキル基、C2〜C40のアルケニル基、C1〜C40のアルコキシ基、C3〜C40のシクロアルキル基、C3〜C40のヘテロシクロアルキル基、C6〜C40のアリール基、およびC5〜C40のヘテロアリール基からなる群から選択された一つ以上の基で置換または非置換されたC6〜C40のアリールアミノ基からなる群から選択される。
1)ハロゲン基が置換されているアントラキノン誘導体とR4置換体を有するボロン酸またはボロンエステル化合物をPd触媒下でスズキカップリングしてR4が置換されたアントラキノン誘導体を製造するステップ、
2)前記1)ステップで製造されたアントラキノン誘導体からジアルコール誘導体を製造するステップ、および
3)前記2)ステップで製造されたジアルコール誘導体を還元してアントラセン誘導体を製造するステップ、
を含む方法によって製造され得る。このような製造方法は下記反応式1で表示される。
1)ハロゲン基が置換されているアントラキノン誘導体にPd触媒下でアリールアミノ基を導入してアントラキノン誘導体を製造するステップ、
2)前記1)ステップで製造されたアントラキノン誘導体からジアルコール誘導体を製造するステップ、および
3)前記2)ステップで製造されたジアルコール誘導体を還元してアントラセン誘導体を製造するステップ、
を含む方法によって製造され得る。
1)ハロゲン基が置換されたアントラキノン誘導体からジアルコール誘導体を製造するステップ、
2)前記1)ステップで製造されたジアルコール誘導体を還元してアントラセン誘導体を製造するステップ、
3)前記2)ステップで製造されたアントラセン誘導体からアントラセンボロンエステル誘導体を製造するステップ、および
4)前記3)ステップで製造されたアントラセンボロンエステル誘導体とR4のハロゲン化物をPd触媒下でスズキカップリングしてR4が置換された化学式1の化合物を製造するステップ、
を含む方法によって製造され得る。このような製造方法は下記反応式2で表示される。
UV(2×10−5Mトルエン溶液):λmax398、376nm
PL(2×10−5Mトルエン溶液):λmax454nm
UV(2×10−5Mトルエン溶液):λmax398、379nm
PL(2×10−5Mトルエン溶液):λmax458nm
UV(2×10−5Mトルエン溶液):λmax385、548nm
PL(2×10−5Mトルエン溶液):λmax360、377、399nm
UV(2×10−5Mトルエン溶液):λmax400、382nm
PL(2×10−5Mトルエン溶液):λmax462nm
UV(2×10−5Mトルエン溶液):λmax438、491nm
PL(2×10−5Mトルエン溶液):λmax526nm
UV(2×10−5Mトルエン溶液):λmax298、389、400nm
UV(2×10−5Mトルエン溶液):λmax380、400nm
ITO(indium tin oxide)が1,500Åの厚さで薄膜コーティングされたガラス基板を、洗剤を溶かした蒸留水に入れて超音波で洗浄した。この時、洗剤はフィッシャ社(Fischer Co.)製を用い、蒸留水はミリポア社(Millipore Co.)製のフィルターで2回濾過した蒸留水を使用した。ITOを30分間洗浄した後、蒸留水で2回繰り返して超音波洗浄を10分間進行した。蒸留水洗浄が終わった後、イソプロピルアルコール、アセトン、メタノールの溶剤で超音波洗浄をして乾燥させた後、プラズマ洗浄機で輸送した。また、酸素プラズマを用いて前記基板を5分間洗浄した後、真空蒸着機で基板を輸送した。
前記実施例1と同様の方法で製造されたITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)(400Å)、Alq3(300Å)、化学式1−10(200Å)の化合物を順次熱真空蒸着して正孔注入層、正孔輸送層、および発光層、電子輸送層を順に形成した。
前記実施例1と同様の方法で製造されたITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)(400Å)、化学式1−11(400Å)の化合物を順次熱真空蒸着して正孔注入層、正孔輸送層、および発光と電子輸送を同時に行う層を順に形成した。
前記実施例1のように用意したITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)(400Å)、および前記化学式1−112の化合物(300Å)、Alq3(200Å)、フッ化リチウム(LiF)12Åを順次熱真空蒸着して、正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層を順に形成した。その上に2,000Åの厚さのアルミニウムを蒸着して陰極を形成して有機発光素子を製造した。
前記実施例1のように用意したITO電極上にヘキサニトリルヘキサアザトリフェニレン(500Å)、4,4’−ビス[N−(1−ナフチル)−N−フェニルアミノ]ビフェニル(NPB)(400Å)、および前記化学式1−109の化合物(300Å)、Alq3(200Å)、フッ化リチウム(LiF)12Åを順次熱真空蒸着して、正孔注入層、正孔輸送層、発光層、電子輸送層、電子注入層を順に形成した。その上に2,000Åの厚さのアルミニウムを蒸着して陰極を形成して有機発光素子を製造した。
2 陽極
3 正孔注入層
4 正孔輸送層
5 有機発光層
6 電子輸送層
7 陰極
Claims (11)
- 下記化学式1の化合物:
R3およびR4のうち少なくとも一つは下記化学式2の基であり、
前記化学式2において、
L1は、直接結合であるか;C6〜C40のアリーレン基であり、
R1およびR2は、互いに独立してC6〜C40のアリール基であり、
R5およびR6は、水素であり、
Ar1は、C6〜C40のアリール基;フェニル基、ナフチル基、またはビフェニル基で置換または非置換されたベンゾイミダゾール基;ベンゾチアゾール基;ベンゾキサゾール基;カルバゾール基;及びフェニル基で置換または非置換されたトリアゾール基からなる群より選択される少なくとも1つで置換または非置換されたC6〜C40のアリール基である。 - 前記化学式1のR1およびR2は、同一のアリール基である請求項1に記載の化合物。
- 第1電極、第2電極、および前記第1電極と第2電極との間に配置された1層以上の有機物層を含む有機電子素子であって、前記有機物層のうち1層以上は請求項1ないし3のうち何れか一項の化合物を含む有機電子素子。
- 前記有機電子素子は、有機発光素子、有機太陽電池、有機感光体(OPC)ドラム、および有機トランジスタからなる群から選択される請求項4に記載の有機電子素子。
- 前記有機電子素子は、有機発光素子である請求項4に記載の有機電子素子。
- 前記有機発光素子は、基板上に陽極、1層以上の有機物層、および陰極が順次積層された正方向構造の有機発光素子である請求項6に記載の有機電子素子。
- 前記有機発光素子は、基板上に陰極、1層以上の有機物層、および陽極が順次積層された逆方向構造の有機発光素子である請求項6に記載の有機電子素子。
- 前記有機発光素子の有機物層は、正孔注入層、正孔輸送層、発光層、および電子注入並びに輸送層を含む請求項6に記載の有機電子素子。
- 前記有機発光素子の有機物層は、発光層を含み、この発光層が請求項1ないし3のうち何れか一項の化合物を含む請求項6に記載の有機電子素子。
- 前記有機発光素子の有機物層は、電子輸送層、電子注入層、または電子輸送および電子注入層を含み、この電子輸送層、電子注入層、または電子輸送および電子注入層が請求項1ないし3のうち何れか一項の化合物を含む請求項6に記載の有機電子素子。
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JP4317476B2 (ja) | 2004-03-29 | 2009-08-19 | Tdk株式会社 | 有機el素子及び有機elディスプレイ |
KR100590004B1 (ko) | 2004-09-02 | 2006-06-19 | 위니아만도 주식회사 | 이온정수기 |
US7776456B2 (en) * | 2004-12-03 | 2010-08-17 | Universal Display Corporation | Organic light emitting devices with an emissive region having emissive and non-emissive layers and method of making |
US8053762B2 (en) * | 2005-12-13 | 2011-11-08 | Lg Chem, Ltd. | Imidazoquinazoline derivative, process for preparing the same, and organic electronic device using the same |
KR100872692B1 (ko) * | 2006-03-06 | 2008-12-10 | 주식회사 엘지화학 | 신규한 안트라센 유도체 및 이를 이용한 유기 전자 소자 |
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JP5417702B2 (ja) * | 2006-11-02 | 2014-02-19 | 三菱化学株式会社 | 有機電界蛍光発光素子、有機電界蛍光発光層塗布溶液、カラーディスプレイ表示装置 |
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US7965032B2 (en) | 2011-06-21 |
CN101395105B (zh) | 2014-04-30 |
JP2009529035A (ja) | 2009-08-13 |
TW200738586A (en) | 2007-10-16 |
EP1991514B1 (en) | 2017-12-20 |
TWI348463B (en) | 2011-09-11 |
KR20070091540A (ko) | 2007-09-11 |
EP1991514A4 (en) | 2009-03-25 |
CN101395105A (zh) | 2009-03-25 |
WO2007102683A1 (en) | 2007-09-13 |
EP2364964A1 (en) | 2011-09-14 |
JP2013136582A (ja) | 2013-07-11 |
KR100872692B1 (ko) | 2008-12-10 |
EP2364964B1 (en) | 2016-03-02 |
US20070205412A1 (en) | 2007-09-06 |
EP1991514A1 (en) | 2008-11-19 |
WO2007102683A9 (en) | 2008-12-24 |
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