JP5801074B2 - ヘテロ環化合物及びこれを含む有機発光素子 - Google Patents
ヘテロ環化合物及びこれを含む有機発光素子 Download PDFInfo
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- JP5801074B2 JP5801074B2 JP2011067598A JP2011067598A JP5801074B2 JP 5801074 B2 JP5801074 B2 JP 5801074B2 JP 2011067598 A JP2011067598 A JP 2011067598A JP 2011067598 A JP2011067598 A JP 2011067598A JP 5801074 B2 JP5801074 B2 JP 5801074B2
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- alkyl
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- imidazole
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 153
- 239000010410 layer Substances 0.000 claims description 133
- 125000003118 aryl group Chemical group 0.000 claims description 122
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 81
- -1 benzoimidazolyl groups Chemical group 0.000 claims description 75
- 238000002347 injection Methods 0.000 claims description 49
- 239000007924 injection Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000000126 substance Substances 0.000 claims description 32
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 27
- 125000001624 naphthyl group Chemical group 0.000 claims description 27
- 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 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 23
- 125000005561 phenanthryl group Chemical group 0.000 claims description 22
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 21
- 125000001725 pyrenyl group Chemical group 0.000 claims description 21
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 19
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 15
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000004957 naphthylene group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 125000004431 deuterium atom Chemical group 0.000 claims description 9
- 125000005567 fluorenylene group Chemical group 0.000 claims description 9
- 125000005551 pyridylene group Chemical group 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- 125000004653 anthracenylene group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000005566 carbazolylene group Chemical group 0.000 claims description 6
- 125000006383 alkylpyridyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 23
- 239000000463 material Substances 0.000 description 23
- 230000005525 hole transport Effects 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 125000001424 substituent group Chemical group 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 12
- 238000004528 spin coating Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 230000000903 blocking effect Effects 0.000 description 10
- 238000004896 high resolution mass spectrometry Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 238000001771 vacuum deposition Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 8
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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 6
- AHCDKANCCBEQJJ-UHFFFAOYSA-N 9-bromo-9h-fluorene Chemical compound C1=CC=C2C(Br)C3=CC=CC=C3C2=C1 AHCDKANCCBEQJJ-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 4
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 4
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 229940125851 compound 27 Drugs 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 3
- 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 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- 229940126086 compound 21 Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 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 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 2
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 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 2
- 239000011575 calcium Substances 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000005584 chrysenylene group Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- OANQELUUJGCUOQ-UHFFFAOYSA-N hexaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 OANQELUUJGCUOQ-UHFFFAOYSA-N 0.000 description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- HTISDHGSRIQJEV-UHFFFAOYSA-N octacyclo[36.4.0.02,7.08,13.014,19.020,25.026,31.032,37]dotetraconta-1(42),2,4,6,8,10,12,14,16,18,20,22,24,26,28,30,32,34,36,38,40-henicosaene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 HTISDHGSRIQJEV-UHFFFAOYSA-N 0.000 description 2
- 125000005565 oxadiazolylene group Chemical group 0.000 description 2
- 125000005564 oxazolylene group Chemical group 0.000 description 2
- MHAUGLFOVCQYNR-UHFFFAOYSA-N pentaphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 MHAUGLFOVCQYNR-UHFFFAOYSA-N 0.000 description 2
- 125000005560 phenanthrenylene group Chemical group 0.000 description 2
- 125000005550 pyrazinylene group Chemical group 0.000 description 2
- 125000005548 pyrenylene group Chemical group 0.000 description 2
- 125000005576 pyrimidinylene group Chemical group 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000005557 thiazolylene group Chemical group 0.000 description 2
- 125000005730 thiophenylene group Chemical group 0.000 description 2
- 125000005559 triazolylene group Chemical group 0.000 description 2
- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 1
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- OGNSDRMLWYNUED-UHFFFAOYSA-N 1-cyclohexyl-4-[4-[4-(4-cyclohexylcyclohexyl)cyclohexyl]cyclohexyl]cyclohexane Chemical group C1CCCCC1C1CCC(C2CCC(CC2)C2CCC(CC2)C2CCC(CC2)C2CCCCC2)CC1 OGNSDRMLWYNUED-UHFFFAOYSA-N 0.000 description 1
- MCZUXEWWARACSP-UHFFFAOYSA-N 1-ethynylnaphthalene Chemical group C1=CC=C2C(C#C)=CC=CC2=C1 MCZUXEWWARACSP-UHFFFAOYSA-N 0.000 description 1
- BFTIPCRZWILUIY-UHFFFAOYSA-N 2,5,8,11-tetratert-butylperylene Chemical group CC(C)(C)C1=CC(C2=CC(C(C)(C)C)=CC=3C2=C2C=C(C=3)C(C)(C)C)=C3C2=CC(C(C)(C)C)=CC3=C1 BFTIPCRZWILUIY-UHFFFAOYSA-N 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-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
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical group CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 description 1
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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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
- C07D487/22—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 four or more hetero rings
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Description
また、本発明の一具現例による有機発光素子の1層以上の層は、前記化学式1の化合物を使用して蒸着方法で形成することができ、または溶液で製造された化学式1の化合物をコーティングする湿式方法でも形成することができる。
6,12−ジブロモクリセン3.84g(10mmol)、ベンゾフェノンヒドラゾン2.16g(11mmol)、t−BuONa 1.44g(15mmol)、Pd(OAc)2 45mg(0.2mmol)、および2−ジシクロヘキシルホスフィノ−2’,4’,6’−トリイソプロピルフェニル82mg(0.2mmol)を、トルエン50mLに溶かした後、90℃で3時間撹拌した。常温に冷やした反応物に蒸溜水を加え、ジエチルエーテル80mLで2回、ジクロロメタン80mLで1回抽出した。集めた有機層を硫酸マグネシウムで乾燥させて濾過した後で溶媒を蒸発させ、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、中間体1を5.7g(収率92%)得た。生成された化合物は、HR−MS(high resolution mass spectrometry)によって確認した(calc:616.2627,found:616.2618)。
中間体1 6.2g(10mmol)、p−トルエンスルホン酸一水和物3.8g(20mmol)及びメチルエチルケトン50mLを加えた後、110℃で24時間撹拌した。常温に冷やした反応物に蒸溜水を加え、ジエチルエーテル80mLで2回、ジクロロメタン80mLで2回抽出した。集めた有機層を硫酸マグネシウムで乾燥させて濾過した後で溶媒を蒸発させ、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、中間体2を2.5g(収率69%)得た。生成された化合物は、HR−MSによって確認した(calc:360.1626,found:360.1513)。
窒素下で、中間体2 2.5g(70mmol)、9−ブロモフルオレン3.8g(14mmol)、t−BuONa 2.0g(21mmol)、Pd2(dba)3 260mg(0.28mmol)及びP(t−Bu)3 56mg(0.28mmol)を、トルエン50mLに溶かした後、90℃で3時間撹拌した。前記反応が完結した後、常温に冷やし、これを、蒸溜水とジエチルエーテル50mLとで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させて溶媒を蒸発させ、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、化合物4を3.5g(収率67%)得た。生成した化合物は、HR−MSによって確認した(calc:746.3661,found:746.3761)。
中間体3の合成
中間体4の合成
アノードとして、コーニング(Corning)15Ω/cm2(1,200Å)ITOガラス基板を、50mm×50mm×0.7mmサイズに切りイソプロピルアルコールと純水とを利用し、それぞれ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備え付けた。
電子輸送層の形成時に、前記化合物4の代わりに化合物20を利用したことを除いては、実施例1と同一にし、有機発光素子を製作した。
電子輸送層の形成時に、前記化合物4の代わりに化合物21を利用したことを除いては、実施例1と同一にし、有機発光素子を製作した。
電子輸送層の形成時に、前記化合物4の代わりに化合物27を利用したことを除いては、実施例1と同一にし、有機発光素子を製作した。
電子輸送層の形成時に、前記化合物4の代わりに化合物28を利用したことを除いては、実施例1と同一にし、有機発光素子を製作した。
Claims (9)
- 下記化学式2で表示されるヘテロ環化合物:
R1及びR8は互いに独立して、−(Ar1)a−(Ar11)で表示される基からなる群から選択され、
R2,R3,R9及びR10は互いに独立して、置換または非置換のC1−C50アルキル基、−(Ar1)a−(Ar11)で表示される基からなる群から選択され、
Ar1は、置換または非置換のC5−C20アリーレン基、及び置換または非置換のC4−C20ヘテロアリーレン基からなる群から選択され、
Ar11は、置換または非置換のC5−C20アリール基、及び置換または非置換のC4−C20ヘテロアリール基からなる群から選択され、
aは、0,1,2または3であり、
−(Ar1)a−(Ar11)で表示される基において、a個のAr1は、互いに同一であるか異なりうる。 - 前記Ar1は、フェニレン基、C1−C10アルキルフェニレン基、ジ(C1−C10アルキル)フェニレン基、ナフチレン基、C1−C10アルキルナフチレン基、ジ(C1−C10アルキル)ナフチレン基、アントリレン基、C1−C10アルキルアントリレン基、ジ(C1−C10アルキル)アントリレン基、フルオレニレン基、C1−C10アルキルフルオレニレン基、ジ(C1−C10アルキル)フルオレニレン基、C6−C14アリールフルオレニレン基、ジ(C6−C14アリール)フルオレニレン基、ピリジレン基、C1−C10アルキルピリジレン基、ジ(C1−C10アルキル)ピリジレン基、カルバゾリレン基、C1−C10アルキルカルバゾリレン基、ジ(C1−C10アルキル)カルバゾリレン基からなる群から選択されることを特徴とする請求項1に記載のヘテロ環化合物。
- 前記Ar11は、フェニル基、C1−C10アルキルフェニル基、ジ(C1−C10アルキル)フェニル基、C6−C14アリールフェニル基、ジ(C6−C14アリール)フェニル基、ナフチル基、C1−C10アルキルナフチル基、ジ(C1−C10アルキル)ナフチル基、C6−C14アリールナフチル基、ジ(C6−C14アリール)ナフチル基、アントリル基、C1−C10アルキルアントリル基、ジ(C1−C10アルキル)アントリル基、C6−C14アリールアントリル基、ジ(C6−C14アリール)アントリル基、フェナントリル基、C1−C10アルキルフェナントリル基、ジ(C1−C10アルキル)フェナントリル基、C6−C14アリールフェナントリル基、ジ(C6−C14アリール)フェナントリル基、フルオレニル基、C1−C10アルキルフルオレニル基、ジ(C1−C10アルキル)フルオレニル基、C6−C14アリールフルオレニル基、ジ(C6−C14アリール)フルオレニル基、ピリジル基、C1−C10アルキルピリジル基、ジ(C1−C10アルキル)ピリジル基、ピレニル基、C1−C10アルキルピレニル基、ジ(C1−C10アルキル)ピレニル基、C6−C14アリールピレニル基、ジ(C6−C14アリール)ピレニル基、フェナントロリニル基、C1−C10アルキルフェナントロリニル基、ジ(C1−C10アルキル)フェナントロリニル基、C6−C14アリールフェナントロリニル基、ジ(C6−C14アリール)フェナントロリニル基、キノリニル基、C1−C10アルキルキノリニル基、ジ(C1−C10アルキル)キノリニル基、C6−C14アリールキノリニル基、ジ(C6−C14アリール)キノリニル基、ベンゾオキサゾリル基、C1−C10アルキルベンゾオキサゾリル基、ジ(C1−C10アルキル)ベンゾオキサゾリル基、C6−C14アリールベンゾオキサゾリル基、ジ(C6−C14アリール)ベンゾオキサゾリル基、ベンゾチアゾリル基、C1−C10アルキルベンゾチアゾリル基、ジ(C1−C10アルキル)ベンゾチアゾリル基、C6−C14アリールベンゾチアゾリル基、ジ(C6−C14アリール)ベンゾチアゾリル基、ベンゾイミダゾリル基、C1−C10アルキルベンゾイミダゾリル基、ジ(C1−C10アルキル)ベンゾイミダゾリル基、C6−C14アリールベンゾイミダゾリル基、ジ(C6−C14アリール)ベンゾイミダゾリル基、イミダゾールピリジニル基、C1−C10アルキルイミダゾールピリジニル基、ジ(C1−C10アルキル)イミダゾールピリジニル基、C6−C14アリールイミダゾールピリジニル基、ジ(C6−C14アリール)イミダゾールピリジニル基、イミダゾールピリミジニル基、C1−C10アルキルイミダゾールピリミジニル基、ジ(C1−C10アルキル)イミダゾールピリミジニル基、C6−C14アリールイミダゾールピリミジニル基、ジ(C6−C14アリール)イミダゾールピリミジニル基、カルバゾリル基、C1−C10アルキルカルバゾリル基、ジ(C1−C10アルキル)カルバゾリル基、C6−C14アリールカルバゾリル基、ジ(C6−C14アリール)カルバゾリル基からなる群から選択されることを特徴とする請求項1に記載のヘテロ環化合物。
- 前記R1及びR8は互いに独立して、−(Ar1)a−(Ar11)で表示される基から選択され、前記R2,R3,R9及びR10は互いに独立して、メチル基、フェニル基からなる群から選択され、
前記Ar1は、置換または非置換のC5−C20アリーレン基、及び置換または非置換のC4−C20ヘテロアリーレン基からなる群から選択され、
前記Ar11は、フェニル基、C1−C10アルキルフェニル基、ジ(C1−C10アルキル)フェニル基、C6−C14アリールフェニル基、ジ(C6−C14アリール)フェニル基、ナフチル基、C1−C10アルキルナフチル基、ジ(C1−C10アルキル)ナフチル基、C6−C14アリールナフチル基、ジ(C6−C14アリール)ナフチル基、アントリル基、C1−C10アルキルアントリル基、ジ(C1−C10アルキル)アントリル基、C6−C14アリールアントリル基、ジ(C6−C14アリール)アントリル基、フェナントリル基、C1−C10アルキルフェナントリル基、ジ(C1−C10アルキル)フェナントリル基、C6−C14アリールフェナントリル基、ジ(C6−C14アリール)フェナントリル基、フルオレニル基、C1−C10アルキルフルオレニル基、ジ(C1−C10アルキル)フルオレニル基、C6−C14アリールフルオレニル基、ジ(C6−C14アリール)フルオレニル基、ピリジル基、C1−C10アルキルピリジル基、ジ(C1−C10アルキル)ピリジル基、ピレニル基、C1−C10アルキルピレニル基、ジ(C1−C10アルキル)ピレニル基、C6−C14アリールピレニル基、ジ(C6−C14アリール)ピレニル基、フェナントロリニル基、C1−C10アルキルフェナントロリニル基、ジ(C1−C10アルキル)フェナントロリニル基、C6−C14アリールフェナントロリニル基、ジ(C6−C14アリール)フェナントロリニル基、キノリニル基、C1−C10アルキルキノリニル基、ジ(C1−C10アルキル)キノリニル基、C6−C14アリールキノリニル基、ジ(C6−C14アリール)キノリニル基、ベンゾオキサゾリル基、C1−C10アルキルベンゾオキサゾリル基、ジ(C1−C10アルキル)ベンゾオキサゾリル基、C6−C14アリールベンゾオキサゾリル基、ジ(C6−C14アリール)ベンゾオキサゾリル基、ベンゾチアゾリル基、C1−C10アルキルベンゾチアゾリル基、ジ(C1−C10アルキル)ベンゾチアゾリル基、C6−C14アリールベンゾチアゾリル基、ジ(C6−C14アリール)ベンゾチアゾリル基、ベンゾイミダゾリル基、C1−C10アルキルベンゾイミダゾリル基、ジ(C1−C10アルキル)ベンゾイミダゾリル基、C6−C14アリールベンゾイミダゾリル基、ジ(C6−C14アリール)ベンゾイミダゾリル基、イミダゾールピリジニル基、C1−C10アルキルイミダゾールピリジニル基、ジ(C1−C10アルキル)イミダゾールピリジニル基、C6−C14アリールイミダゾールピリジニル基、ジ(C6−C14アリール)イミダゾールピリジニル基、イミダゾールピリミジニル基、C1−C10アルキルイミダゾールピリミジニル基、ジ(C1−C10アルキル)イミダゾールピリミジニル基、C6−C14アリールイミダゾールピリミジニル基、ジ(C6−C14アリール)イミダゾールピリミジニル基、カルバゾリル基、C1−C10アルキルカルバゾリル基、ジ(C1−C10アルキル)カルバゾリル基、C6−C14アリールカルバゾリル基、ジ(C6−C14アリール)カルバゾリル基からなる群から選択され、
前記aは、0,1,2または3であることを特徴とする請求項1に記載のヘテロ環化合物。 - 第1電極と、前記第1電極に対向した第2電極と、前記第1電極と前記第2電極との間に介在した有機層と、を具備し、前記有機層が請求項1ないし請求項7のうち、いずれか1項に記載のヘテロ環化合物を含む有機発光素子。
- 前記有機層が、電子注入層、電子輸送層または発光層であることを特徴とする請求項8に記載の有機発光素子。
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CN107108494A (zh) | 2014-12-26 | 2017-08-29 | 陶氏环球技术有限责任公司 | 有机化合物和包含包括有机化合物的有机层的电子装置 |
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Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL275143A (ja) * | 1961-02-23 | |||
JP3229654B2 (ja) | 1992-06-05 | 2001-11-19 | ティーディーケイ株式会社 | 有機el素子用化合物および有機el素子 |
JP3816969B2 (ja) | 1994-04-26 | 2006-08-30 | Tdk株式会社 | 有機el素子 |
DE69511755T2 (de) | 1994-04-26 | 2000-01-13 | Tdk Corp | Phenylanthracenderivat und organisches EL-Element |
US5645948A (en) | 1996-08-20 | 1997-07-08 | Eastman Kodak Company | Blue organic electroluminescent devices |
US5972247A (en) | 1998-03-20 | 1999-10-26 | Eastman Kodak Company | Organic electroluminescent elements for stable blue electroluminescent devices |
JP2000003782A (ja) | 1998-06-12 | 2000-01-07 | Casio Comput Co Ltd | 電界発光素子 |
EP1009043A3 (en) | 1998-12-09 | 2002-07-03 | Eastman Kodak Company | Electroluminescent device with polyphenyl hydrocarbon hole transport layer |
US6465115B2 (en) | 1998-12-09 | 2002-10-15 | Eastman Kodak Company | Electroluminescent device with anthracene derivatives hole transport layer |
TWI314947B (en) | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
KR101178006B1 (ko) * | 2002-07-19 | 2012-08-28 | 이데미쓰 고산 가부시키가이샤 | 유기 전기발광 소자 및 유기 발광 매체 |
US20060052641A1 (en) | 2002-11-12 | 2006-03-09 | Masakazu Funahashi | Material for organic electroluminescent device and organic electroluminescent device using same |
JP2006052324A (ja) | 2004-08-12 | 2006-02-23 | Sony Corp | 有機材料、有機電界発光素子、および表示装置 |
WO2006025273A1 (ja) | 2004-08-31 | 2006-03-09 | Idemitsu Kosan Co., Ltd. | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
JP4263700B2 (ja) | 2005-03-15 | 2009-05-13 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
CN101184822B (zh) | 2005-05-30 | 2014-11-26 | 西巴特殊化学品控股有限公司 | 电致发光器件 |
JP5055818B2 (ja) | 2006-04-19 | 2012-10-24 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP4830750B2 (ja) | 2006-09-21 | 2011-12-07 | 東レ株式会社 | 発光素子材料および発光素子 |
KR20080047209A (ko) | 2006-11-24 | 2008-05-28 | 삼성전자주식회사 | 유기 발광 화합물 및 이를 구비한 유기 발광 소자 |
JP2008218987A (ja) | 2007-02-06 | 2008-09-18 | Sumitomo Chemical Co Ltd | 組成物及び該組成物を用いてなる発光素子 |
KR100874472B1 (ko) | 2007-02-28 | 2008-12-18 | 에스에프씨 주식회사 | 청색발광화합물 및 이를 이용한 유기전계발광소자 |
JP5142589B2 (ja) | 2007-05-28 | 2013-02-13 | キヤノン株式会社 | インデノクリセン誘導体及びそれを用いた有機発光素子 |
CN101679207B (zh) | 2007-06-01 | 2014-05-28 | E.I.内穆尔杜邦公司 | 用于深蓝色发光应用的* |
JP2010241688A (ja) | 2007-07-07 | 2010-10-28 | Idemitsu Kosan Co Ltd | 非対称クリセン誘導体、有機el素子用材料、有機el素子用発光材料、及び、有機el素子 |
JP5074879B2 (ja) | 2007-10-16 | 2012-11-14 | 双葉電子工業株式会社 | 電子放出素子及び表示素子 |
US8216753B2 (en) * | 2007-12-13 | 2012-07-10 | E I Du Pont De Nemours And Company | Electroactive materials |
JP2010073987A (ja) | 2008-09-19 | 2010-04-02 | Idemitsu Kosan Co Ltd | 有機薄膜太陽電池用材料 |
JP5366505B2 (ja) | 2008-11-06 | 2013-12-11 | キヤノン株式会社 | インデノピレン化合物及びこれを用いた有機発光素子 |
KR101603070B1 (ko) | 2009-03-31 | 2016-03-14 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 |
KR101202347B1 (ko) | 2009-10-09 | 2012-11-16 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기층을 구비한 유기 발광 소자 |
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KR101736987B1 (ko) | 2017-05-18 |
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