JP2009120610A - 複素環化合物及びそれを利用した有機電界発光装置 - Google Patents
複素環化合物及びそれを利用した有機電界発光装置 Download PDFInfo
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- JP2009120610A JP2009120610A JP2008289881A JP2008289881A JP2009120610A JP 2009120610 A JP2009120610 A JP 2009120610A JP 2008289881 A JP2008289881 A JP 2008289881A JP 2008289881 A JP2008289881 A JP 2008289881A JP 2009120610 A JP2009120610 A JP 2009120610A
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- organic electroluminescent
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- electroluminescent device
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 7
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
- 229910052796 boron Inorganic materials 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011574 phosphorus Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 32
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 96
- -1 ethylphenyl group Chemical group 0.000 description 41
- 238000002347 injection Methods 0.000 description 33
- 239000007924 injection Substances 0.000 description 33
- 238000000034 method Methods 0.000 description 33
- 238000004528 spin coating Methods 0.000 description 20
- 238000001771 vacuum deposition Methods 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229940125797 compound 12 Drugs 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 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 6
- 238000005406 washing Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 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 5
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 3
- BWAPJIHJXDYDPW-UHFFFAOYSA-N 2,5-dimethyl-p-phenylenediamine Chemical compound CC1=CC(N)=C(C)C=C1N BWAPJIHJXDYDPW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 3
- 125000004802 cyanophenyl group Chemical group 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 2
- HXWWMGJBPGRWRS-CMDGGOBGSA-N 4- -2-tert-butyl-6- -4h-pyran Chemical compound O1C(C(C)(C)C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 HXWWMGJBPGRWRS-CMDGGOBGSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229910006404 SnO 2 Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000001412 amines Chemical class 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
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000003828 azulenyl group Chemical group 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000004212 difluorophenyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 0 **1c2cc(C=C(*)*3*)c3cc2C=C1* Chemical compound **1c2cc(C=C(*)*3*)c3cc2C=C1* 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- PRUCJKSKYARXJB-UHFFFAOYSA-N 1-[2-[3,5-bis[2-(9h-carbazol-1-yl)phenyl]phenyl]phenyl]-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C1=CC=CC=C1C1=CC(C=2C(=CC=CC=2)C=2C=3NC4=CC=CC=C4C=3C=CC=2)=CC(C=2C(=CC=CC=2)C=2C=3NC4=CC=CC=C4C=3C=CC=2)=C1 PRUCJKSKYARXJB-UHFFFAOYSA-N 0.000 description 1
- AHBDIQVWSLNELJ-UHFFFAOYSA-N 1-[3,5-bis(9h-carbazol-1-yl)phenyl]-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C1=CC(C=2C=3NC4=CC=CC=C4C=3C=CC=2)=CC(C2=C3NC=4C(C3=CC=C2)=CC=CC=4)=C1 AHBDIQVWSLNELJ-UHFFFAOYSA-N 0.000 description 1
- DBDOZRBRAYSLFX-UHFFFAOYSA-N 1-[4-[4-(9h-carbazol-1-yl)-2-methylphenyl]-3-methylphenyl]-9h-carbazole Chemical group N1C2=CC=CC=C2C2=C1C(C=1C=C(C(=CC=1)C=1C(=CC(=CC=1)C=1C3=C(C4=CC=CC=C4N3)C=CC=1)C)C)=CC=C2 DBDOZRBRAYSLFX-UHFFFAOYSA-N 0.000 description 1
- IERDDDBDINUYCD-UHFFFAOYSA-N 1-[4-[4-(9h-carbazol-1-yl)phenyl]phenyl]-9h-carbazole Chemical group C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 IERDDDBDINUYCD-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-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
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- FJXNABNMUQXOHX-UHFFFAOYSA-N 4-(9h-carbazol-1-yl)-n,n-bis[4-(9h-carbazol-1-yl)phenyl]aniline Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C(C=C1)=CC=C1N(C=1C=CC(=CC=1)C=1C=2NC3=CC=CC=C3C=2C=CC=1)C(C=C1)=CC=C1C1=C2NC3=CC=CC=C3C2=CC=C1 FJXNABNMUQXOHX-UHFFFAOYSA-N 0.000 description 1
- ZNJRONVKWRHYBF-VOTSOKGWSA-N 4-(dicyanomethylene)-2-methyl-6-julolidyl-9-enyl-4h-pyran Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(CCCN2CCC3)=C2C3=C1 ZNJRONVKWRHYBF-VOTSOKGWSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
- AIXZBGVLNVRQSS-UHFFFAOYSA-N 5-tert-butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl)thiophen-2-yl]-1,3-benzoxazole Chemical compound CC(C)(C)C1=CC=C2OC(C3=CC=C(S3)C=3OC4=CC=C(C=C4N=3)C(C)(C)C)=NC2=C1 AIXZBGVLNVRQSS-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- RBZMVGJZECPZCE-UHFFFAOYSA-N CC(C1C=CC(N(c2ccccc2)c(cc2)ccc2-[n](c(-c(cc2)ccc2-c2ccccc2)cc2c3)c2cc(cc2-c(cc4)ccc4-c4ccccc4)c3[n]2-c(cc2)ccc2N(c2ccccc2)c2ccccc2)=CC1)O Chemical compound CC(C1C=CC(N(c2ccccc2)c(cc2)ccc2-[n](c(-c(cc2)ccc2-c2ccccc2)cc2c3)c2cc(cc2-c(cc4)ccc4-c4ccccc4)c3[n]2-c(cc2)ccc2N(c2ccccc2)c2ccccc2)=CC1)O RBZMVGJZECPZCE-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 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
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- YAPIJPOCONTNDY-UHFFFAOYSA-N N1C2=CC=CC=C2C2=C1C(C1=CC=C(C=C1)[SiH2]C=1C=CC(=CC=1)C=1C3=C(C4=CC=CC=C4N3)C=CC=1)=CC=C2 Chemical compound N1C2=CC=CC=C2C2=C1C(C1=CC=C(C=C1)[SiH2]C=1C=CC(=CC=1)C=1C3=C(C4=CC=CC=C4N3)C=CC=1)=CC=C2 YAPIJPOCONTNDY-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- LWVGYAZQWVWHDQ-UHFFFAOYSA-N c(c1cc([n](c(-c(cc2)ccc2-c2ccccc2)c2)-c(cc3)cc(c4c5cccc4)c3[n]5-c3ccccc3)c2cc11)c(-c(cc2)ccc2-c2ccccc2)[n]1-c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 Chemical compound c(c1cc([n](c(-c(cc2)ccc2-c2ccccc2)c2)-c(cc3)cc(c4c5cccc4)c3[n]5-c3ccccc3)c2cc11)c(-c(cc2)ccc2-c2ccccc2)[n]1-c(cc1)cc(c2ccccc22)c1[n]2-c1ccccc1 LWVGYAZQWVWHDQ-UHFFFAOYSA-N 0.000 description 1
- VPQOHAIMYUAVBN-UHFFFAOYSA-N c(c1cc([n](c(-c(cc2)ccc2-c2ccccc2)c2)-c(cc3)ccc3-[n]3c4ccccc4c4c3cccc4)c2cc11)c(-c(cc2)ccc2-c2ccccc2)[n]1-c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2 Chemical compound c(c1cc([n](c(-c(cc2)ccc2-c2ccccc2)c2)-c(cc3)ccc3-[n]3c4ccccc4c4c3cccc4)c2cc11)c(-c(cc2)ccc2-c2ccccc2)[n]1-c(cc1)ccc1-[n]1c(cccc2)c2c2c1cccc2 VPQOHAIMYUAVBN-UHFFFAOYSA-N 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- MQCHTHJRANYSEJ-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-1-(3-methylphenyl)benzimidazole-5-carboxamide Chemical compound CC1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)NCC=2C(=CC=CC=2)Cl)=C1 MQCHTHJRANYSEJ-UHFFFAOYSA-N 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 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
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
Description
2,5−ジメチル−1,4−フェニレンジアミン1.36g(10.0mmol)と4−ブロモトルエン4.10g(24.0mmol)とをトルエン50mlに溶かした後、ここにt−ブトキシドナトリウム2.88g(30.0mmol)、Pd(dba)2 0.388g(0.40mmol)、トリ−t−ブチルフォスフィン((t−Bu)3P)0.08g(0.40mmol)を加えて80℃で5時間攪拌した。反応液を室温に冷ました後、水50mlを加えてエチルエーテル20mlで3回抽出した。集められた有機層を硫酸マグネシウムで乾燥し、溶媒を蒸発させて得られた残留物をシリカゲルカラムクロマトグラフィで分離精製して中間体A 2.15gを得た(収率68%)。
中間体A 3.16g(10.0mmol)をジクロロメタン50mlに溶かした後、トリエチルアミン4.0mlを添加した。反応液をアイスバス下で冷却させて塩化ベンゾイル4.21g(30.0mmol)を滴下して30℃で1時間攪拌した後、水50mlを加えてエチルエーテル50mlで3回抽出した。集められた有機層を硫酸マグネシウムで乾燥して溶媒を蒸発させて得られた残留物をDMFで再結晶した。生成された化合物をアセトンで洗浄しつつ濾過して、白色の固体の中間体B 2.99gを得た(収率57%)。
中間体B 5.24g(10mmol)とt−ブトキシドカリウム12.2g(100mmol)とを十分に粉砕攪拌した混合物を高圧反応器に入れて340℃〜350℃、5MPaで2時間反応させた。この反応が完結された後、常温に冷まし、生成されたタール相を粉砕、中和させた後、蒸溜水で洗浄しつつ濾過して乾燥させた。乾燥して得られた残留物をソックスレー装置でアセトンを使用して二日間精製して、黄色化合物2を0.97g得た(収率20%)。
2,5−ジメチル−1,4−フェニレンジアミン1.36g(10.0mmol)と4−ブロモビフェニル5.13g(22.0mmol)とをトルエン50mlに溶かした後、ここにt−ブトキシドナトリウム2.88g(30.0mmol)、Pd(dba)2 0.388g(0.40mmol)、トリ−t−ブチルフォスフィン0.08g(0.40mmol)を加えて80℃で5時間攪拌した。反応液を室温に冷ました後、水50mlを加えてエチルエーテル50mlで3回抽出した。集められた有機層を硫酸マグネシウムで乾燥して溶媒を蒸発させて得られた残留物をシリカゲルカラムクロマトグラフィで分離精製して中間体C 3.13gを得た(収率71%)。
中間体C 4.40g(10.0mmol)をジクロロメタン50mlに溶かした後、トリエチルアミン4.0mlを添加した。反応液をアイスバス下で冷却させて塩化ベンゾイル4.21g(30.0mmol)を滴下して30℃で1時間攪拌した後、水50mlを加えてエチルエーテル50mlで3回抽出した。集められた有機層を硫酸マグネシウムで乾燥して溶媒を蒸発させて得られた残留物をDMFで再結晶した。生成された化合物をアセトンで洗浄しつつ濾過して白色固体の中間体D 4.34gを得た(収率67%)。
中間体D 6.48g(10mmol)とt−ブトキシドカリウム12.2g(100mmol)とを十分に粉砕攪拌した混合物を高圧反応器に入れて340℃〜350℃、5MPaで2時間反応させた。この反応が完結された後、常温に冷まし、生成されたタール相を粉砕、中和させた後、蒸溜水で洗浄しつつ濾過して乾燥させた。乾燥して得られた残留物をソックスレー装置でアセトンを使用して二日間精製して、薄黄色化合物12を0.86g得た(収率14%)。
2,5−ジメチル−1,4−フェニレンジアミン1.36g(10.0mmol)と4−ブロモベンゼン3.77g(24.0mmol)とをトルエン50mlに溶かした後、ここにt−ブトキシドナトリウム2.88g(30.0mmol)、Pd(dba)2 0.388g(0.40mmol)、トリ−t−ブチルフォスフィン0.08g(0.40mmol)を加えて80℃で5時間間攪拌した。反応液を室温に冷ました後、水50mlを加えてエチルエーテル20mlで3回抽出した。集められた有機層を硫酸マグネシウムで乾燥して溶媒を蒸発させて得られた残留物をシリカゲルカラムクロマトグラフィで分離精製して中間体E 1.78gを得た(収率62%)。
中間体E 4.40g(10.0mmol)をジクロロメタン50mlに溶かした後、トリエチルアミン4.0mlを添加した。反応液をアイスバス下で冷却させて4−塩化ビフェニルカルボニル6.50g(30.0mmol)を滴下して30℃で1時間攪拌した後、水50mlを加えてエチルエーテル50mlで3回抽出した。集められた有機層を硫酸マグネシウムで乾燥して溶媒を蒸発させて得られた残留物をDMFで再結晶した。生成された化合物をアセトンで洗浄しつつ濾過して薄黄色固体の中間体F 4.21gを得た(収率65%)。
中間体F 6.48g(10mmol)とt−ブトキシドカリウム12.2g(100mmol)とを十分に粉砕攪拌した混合物を高圧反応器に入れて340℃〜350℃、5MPaで2時間反応させた。この反応が完結された後、常温に冷まし、生成されたタール相を粉砕、中和させた後、蒸溜水で洗浄しつつ濾過して乾燥させた。乾燥して得られた残留物をソックスレー装置でアセトンを使用して二日間精製して薄黄色化合物12を1.12g得た(収率18%)。
アノードとしてコーニング社の15Ω/cm2(1200Å)のITOガラス基板を50mm×50mm×0.7mmのサイズに切断してイソプロピルアルコールと純水とを利用して各5分間超音波洗浄した後、30分間紫外線を照射してオゾンに露出させて洗浄し、真空蒸着装置にこのガラス基板を設置した。
発光層の形成時、下記構造式の化合物と本発明の化合物12とを重量比98:2で同時に蒸着して300Åの厚さに発光層を形成したことを除いては、実施例1と同様にして有機発光装置を製作した。
Claims (7)
- 前記Ar1、Ar2、Ar3及びAr4は、それぞれ独立的に、フェニル基、ナフチル基、ビフェニル基、ターフェニル基、フルオレニル基、カルバゾリル基、ピリジル基、キノリル基、またはこれらの一つ以上の水素がC1−C5の低級アルキル基、C1−C5の低級アルコキシ基、シアノ基、アミン基、フェノキシ基、フェニル基またはハロゲン基に置換されたものから選択される、請求項1に記載の複素環化合物。
- 前記Ar1と前記Ar3とは、同一であり、及び前記Ar2と前記Ar4とは、同一である、請求項1又は2に記載の複素環化合物。
- 前記Xは窒素である、請求項1ないし3のうちいずれか1項に記載の複素環化合物。
- 第1電極、第2電極、及び前記第1電極と前記第2電極との間に位置する有機膜を備える有機電界発光装置において、前記有機膜が請求項1ないし5のうちいずれか1項に記載の複素環化合物を含む、有機電界発光装置。
- 前記有機膜は青色発光層である、請求項6に記載の有機電界発光装置。
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- 2008-11-12 CN CN2008101673836A patent/CN101434605B/zh active Active
- 2008-11-12 JP JP2008289881A patent/JP4994344B2/ja active Active
- 2008-11-14 EP EP08291066A patent/EP2060574B1/en active Active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012005342A1 (en) * | 2010-07-06 | 2012-01-12 | Canon Kabushiki Kaisha | Novel organic compound and organic light-emitting device including the same |
JP2012017272A (ja) * | 2010-07-06 | 2012-01-26 | Canon Inc | 新規有機化合物およびそれを有する有機発光素子 |
Also Published As
Publication number | Publication date |
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EP2060574B1 (en) | 2011-08-17 |
CN101434605A (zh) | 2009-05-20 |
KR100948853B1 (ko) | 2010-03-22 |
EP2060574A1 (en) | 2009-05-20 |
CN101434605B (zh) | 2013-07-17 |
US7846559B2 (en) | 2010-12-07 |
JP4994344B2 (ja) | 2012-08-08 |
KR20090050757A (ko) | 2009-05-20 |
US20090128013A1 (en) | 2009-05-21 |
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