JP2019508427A - ヘテロ環化合物およびこれを含む有機発光素子 - Google Patents
ヘテロ環化合物およびこれを含む有機発光素子 Download PDFInfo
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- JP2019508427A JP2019508427A JP2018544457A JP2018544457A JP2019508427A JP 2019508427 A JP2019508427 A JP 2019508427A JP 2018544457 A JP2018544457 A JP 2018544457A JP 2018544457 A JP2018544457 A JP 2018544457A JP 2019508427 A JP2019508427 A JP 2019508427A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 4
- 239000010410 layer Substances 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 239000000126 substance Substances 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 239000012044 organic layer Substances 0.000 claims description 31
- 238000002347 injection Methods 0.000 claims description 30
- 239000007924 injection Substances 0.000 claims description 30
- 230000005525 hole transport Effects 0.000 claims description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000006267 biphenyl group Chemical group 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000005264 aryl amine group Chemical group 0.000 claims description 14
- 230000001629 suppression Effects 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005462 imide group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- -1 hole transport Substances 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 230000000052 comparative effect Effects 0.000 description 34
- 239000000463 material Substances 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- 230000032258 transport Effects 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 12
- 125000003367 polycyclic group Chemical group 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 11
- 0 C*(C)c1ccccc1C Chemical compound C*(C)c1ccccc1C 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 10
- 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 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229940126214 compound 3 Drugs 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-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
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000005332 alkyl sulfoxy group Chemical group 0.000 description 4
- 229940125797 compound 12 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 3
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 3
- ZKSQIXNEFHHQBJ-UHFFFAOYSA-N 2-(3-bromophenyl)-4-phenyl-6-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC(=CC=C1)Br)C1=CC=CC=C1)C1=CC=CC=C1 ZKSQIXNEFHHQBJ-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- 125000005377 alkyl thioxy group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000003974 aralkylamines Chemical group 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 3
- 125000005165 aryl thioxy group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001716 carbazoles Chemical group 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
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- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 2
- JTMODJXOTWYBOZ-UHFFFAOYSA-N 2-methyl-n-phenylaniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1 JTMODJXOTWYBOZ-UHFFFAOYSA-N 0.000 description 2
- UNTNRNUQVKDIPV-UHFFFAOYSA-N 3h-dithiazole Chemical group N1SSC=C1 UNTNRNUQVKDIPV-UHFFFAOYSA-N 0.000 description 2
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 2
- QXDWMAODKPOTKK-UHFFFAOYSA-N 9-methylanthracen-1-amine Chemical group C1=CC(N)=C2C(C)=C(C=CC=C3)C3=CC2=C1 QXDWMAODKPOTKK-UHFFFAOYSA-N 0.000 description 2
- DVFSOBCDQPUMPJ-UHFFFAOYSA-N CC1(C)c(cc(c(Br)c2)O)c2-c2ccccc12 Chemical compound CC1(C)c(cc(c(Br)c2)O)c2-c2ccccc12 DVFSOBCDQPUMPJ-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical group C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- OJRUMCHLJNCBJV-UHFFFAOYSA-N Oc1cc(C(c2ccccc2-2)(c3ccccc3)c3ccccc3)c-2c2c1c(cccc1)c1[nH]2 Chemical compound Oc1cc(C(c2ccccc2-2)(c3ccccc3)c3ccccc3)c-2c2c1c(cccc1)c1[nH]2 OJRUMCHLJNCBJV-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
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- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 125000005033 thiopyranyl group Chemical group 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
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Abstract
Description
[化学式1]
R1およびR2は、互いに同一でも異なっていてもよく、それぞれ独立して、置換または非置換のアルキル基;または置換または非置換のアリール基であるか、R1およびR2が互いに結合して置換または非置換の環を形成し、
L1およびL2は、互いに同一でも異なっていてもよく、それぞれ独立して、置換または非置換のアリーレン基;または置換または非置換のヘテロアリーレン基であり、
mおよびnは、互いに同一でも異なっていてもよく、それぞれ独立して、0〜5の整数であり、
mが2以上の場合、L1は、互いに同一でも異なっていてもよく、
nが2以上の場合、L2は、互いに同一でも異なっていてもよく、
Ar1およびAr2は、互いに同一でも異なっていてもよく、それぞれ独立して、水素;置換または非置換のアリール基;置換または非置換のアリールアミン基;置換または非置換のヘテロ環基;または置換または非置換のホスフィンオキシド基であり、
R、R´およびR´´は、互いに同一でも異なっていてもよく、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミノ基;置換または非置換のシリル基;置換または非置換のホウ素基;置換または非置換のアルキル基;置換または非置換のシクロアルキル基;置換または非置換のアリールオキシ基;置換または非置換のアルコキシ基;置換または非置換のアリールオキシ基;置換または非置換のアルケニル基;置換または非置換のアラルキル基;置換または非置換のアルキルアリール基;置換または非置換のアルキルアミン基;置換または非置換のアラルキルアミン基;置換または非置換のヘテロアリールアミン基;置換または非置換のアリールアミン基;置換または非置換のアリールホスフィン基;置換または非置換のホスフィンオキシド基;置換または非置換のアリール基;置換または非置換のヘテロ環基であり、
aおよびbは、互いに同一でも異なっていてもよく、それぞれ独立して、0〜4の整数であり、
aが2以上の場合、R´は、互いに同一でも異なっていてもよく、
bが2以上の場合、R´´は、互いに同一でも異なっていてもよい。
および
などの置換されたフルオレニル基であってもよい。ただし、これに限定されるものではない。
[化学式A]
R1、R2、L1、L2、m、n、Ar1、Ar2、R、R´およびR´´の定義は、化学式1および化学式2における定義と同じである。
下記のような反応により中間体を合成した。
[化合物3]
[化合物5]
[化合物6]
[化合物8]
[化合物9]
[化合物10]
[化合物11]
[化合物12]
ITO(indium tin oxide)が1,000Å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。この際、洗剤としてはフィッシャー社(Fischer Co.)製のものを使用し、蒸留水としてはミリポア社(Millipore Co.)製のフィルタ(Filter)で2次に濾過され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分間行った。蒸留水洗浄が終了した後、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行い、乾燥させた後、プラズマ洗浄装置に輸送した。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、真空蒸着装置に基板を輸送した。
[HAT‐CN]
前記実験例1で化合物3の代わりに前記化合物5を使用した以外は、実験例1と同様の方法で有機発光素子を作製した。
前記実験例1で化合物3の代わりに前記化合物6を使用した以外は、実験例1と同様の方法で有機発光素子を作製した。
前記実験例2‐1で化合物3の代わりに前記EB1の化合物を使用した以外は、前記実験例2と同様の方法で有機発光素子を作製した。
前記実験例2‐1で化合物3の代わりに前記EB2の化合物を使用した以外は、前記実験例2と同様の方法で有機発光素子を作製した。
前記合成例で合成された化合物を通常知られている方法で高純度昇華精製をした後、下記のような方法で緑色有機発光素子を製造した。
前記比較例5でCBPの代わりに前記化合物8を使用した以外は、実験例2と同様の方法で有機発光素子を作製した。
前記比較例5で化合物CBPの代わりに前記化合物9を使用した以外は、比較例5と同様の方法で有機発光素子を作製した。
前記比較例5で化合物CBPの代わりに前記化合物10を使用した以外は、比較例5と同様の方法で有機発光素子を作製した。
前記比較例5で化合物CBPの代わりに前記化合物11を使用した以外は、比較例5と同様の方法で有機発光素子を作製した。
前記比較例5で化合物CBPの代わりに前記化合物12を使用した以外は、比較例5と同様の方法で有機発光素子を作製した。
Claims (12)
- 下記化学式1で表される、化合物。
[化学式1]
R1およびR2は、互いに同一でも異なっていてもよく、それぞれ独立して、置換または非置換のアルキル基;または置換または非置換のアリール基であるか、R1およびR2が互いに結合して置換または非置換の環を形成し、
L1およびL2は、互いに同一でも異なっていてもよく、それぞれ独立して、置換または非置換のアリーレン基;または置換または非置換のヘテロアリーレン基であり、
mおよびnは、互いに同一でも異なっていてもよく、それぞれ独立して、0〜5の整数であり、
mが2以上の場合、L1は、互いに同一でも異なっていてもよく、
nが2以上の場合、L2は、互いに同一でも異なっていてもよく、
Ar1およびAr2は、互いに同一でも異なっていてもよく、それぞれ独立して、水素;置換または非置換のアリール基;置換または非置換のアリールアミン基;置換または非置換のヘテロ環基;または置換または非置換のホスフィンオキシド基であり、
R、R´およびR´´は、互いに同一でも異なっていてもよく、それぞれ独立して、水素;重水素;ハロゲン基;ニトリル基;ニトロ基;ヒドロキシ基;カルボニル基;エステル基;イミド基;アミノ基;置換または非置換のシリル基;置換または非置換のホウ素基;置換または非置換のアルキル基;置換または非置換のシクロアルキル基;置換または非置換のアリールオキシ基;置換または非置換のアルコキシ基;置換または非置換のアリールオキシ基;置換または非置換のアルケニル基;置換または非置換のアラルキル基;置換または非置換のアルキルアリール基;置換または非置換のアルキルアミン基;置換または非置換のアラルキルアミン基;置換または非置換のヘテロアリールアミン基;置換または非置換のアリールアミン基;置換または非置換のアリールホスフィン基;置換または非置換のホスフィンオキシド基;置換または非置換のアリール基;置換または非置換のヘテロ環基であり、
aおよびbは、互いに同一でも異なっていてもよく、それぞれ独立して、0〜4の整数であり、
aが2以上の場合、R´は、互いに同一でも異なっていてもよく、
bが2以上の場合、R´´は、互いに同一でも異なっていてもよい。 - 前記Ar1は、フェニル基;ナフチル基;ピリジン基;フェニル基およびビフェニル基からなる群から選択された1以上の置換基で置換されたピリジン基;ピリミジン基;フェニル基およびビフェニル基からなる群から選択された1以上の置換基で置換されたピリミジン基;トリアジン基;フェニル基およびビフェニル基からなる群から選択された1以上の置換基で置換されたトリアジン基;カルバゾール基;またはフェニル基、ビフェニル基およびナフチル基からなる群から選択された1以上で置換されたカルバゾール基である、請求項1または2に記載の化合物。
- 前記Ar2は、水素;フェニル基;フェニル基、ピリジン基、キノリン基およびキナゾリン基からなる群から選択された1以上の置換基で置換されたフェニル基;ビフェニル基;アントラセニル基;フェニル基で置換されたアントラセニル基;ピリジン基;フェニル基およびビフェニル基からなる群から選択された1以上の置換基で置換されたピリジン基;ピリミジン基;フェニル基およびビフェニル基からなる群から選択された1以上の置換基で置換されたピリミジン基;トリアジン基;フェニル基およびビフェニル基からなる群から選択された1以上の置換基で置換されたトリアジン基;ベンゾイミダゾール基;フェニル基で置換されたベンゾイミダゾール基;キノリン基;フェニル基で置換されたキノリン基;キナゾリン基;フェニル基で置換されたキナゾリン基;カルバゾール基;フェニル基で置換されたカルバゾール基;ジベンゾフラン基;ジベンゾチオフェン基;またはフェニル基で置換されたホスフィンオキシド基である、請求項1から3のいずれか一項に記載の化合物。
- 前記R1およびR2は、互いに同一でも異なっていてもよく、それぞれ独立して、メチル基またはフェニル基である、請求項1から5のいずれか一項に記載の化合物。
- 第1の電極と、第2の電極と、前記第1の電極と第2の電極との間に配置された1層以上の有機物層とを含む有機発光素子であって、
前記有機物層のうち1層以上は、請求項1から7のいずれか1項に記載の化合物を含む、有機発光素子。 - 前記有機物層は、電子輸送層、電子注入層、および電子輸送と電子注入を同時に行う層のうち1層以上を含み、前記層のうち1層以上が前記化合物を含む、請求項8に記載の有機発光素子。
- 前記有機物層は、発光層を含み、前記発光層が前記化合物を発光層のホストとして含む、請求項8に記載の有機発光素子。
- 前記有機物層は、正孔注入層、電子抑制層、正孔輸送層、および正孔注入と正孔輸送を同時に行う層のうち1層以上の層を含み、前記層のうち1層以上が前記化合物を含む、請求項8に記載の有機発光素子。
- 前記有機物層は、前記化合物をホストとして含み、他の有機化合物、金属または金属化合物をドーパントとして含む、請求項8に記載の有機発光素子。
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