JP6648882B2 - 有機発光素子 - Google Patents
有機発光素子 Download PDFInfo
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- JP6648882B2 JP6648882B2 JP2018518469A JP2018518469A JP6648882B2 JP 6648882 B2 JP6648882 B2 JP 6648882B2 JP 2018518469 A JP2018518469 A JP 2018518469A JP 2018518469 A JP2018518469 A JP 2018518469A JP 6648882 B2 JP6648882 B2 JP 6648882B2
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- light emitting
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- 150000001875 compounds Chemical class 0.000 claims description 282
- 239000010410 layer Substances 0.000 claims description 187
- 239000000126 substance Substances 0.000 claims description 105
- -1 benzofluorenyl group Chemical group 0.000 claims description 93
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000002347 injection Methods 0.000 claims description 23
- 239000007924 injection Substances 0.000 claims description 23
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 239000011368 organic material Substances 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 13
- 239000012044 organic layer Substances 0.000 claims description 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 11
- XNKVIGSNRYAOQZ-UHFFFAOYSA-N dibenzofluorene Chemical group C12=CC=CC=C2C2=CC=CC=C2C2=C1CC1=CC=CC=C12 XNKVIGSNRYAOQZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003367 polycyclic group Chemical group 0.000 claims description 11
- ZOXHPDJMUUCKNR-UHFFFAOYSA-N anthracene;9h-fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1.C1=CC=CC2=CC3=CC=CC=C3C=C21 ZOXHPDJMUUCKNR-UHFFFAOYSA-N 0.000 claims description 10
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical group C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 6
- 125000005581 pyrene group Chemical group 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 5
- PWGAMUODYKBQLG-UHFFFAOYSA-N N1C2=CC=C[CH]C2=CC2=C1C=CC1=NC3=CC=CC=C3[C]21 Chemical group N1C2=CC=C[CH]C2=CC2=C1C=CC1=NC3=CC=CC=C3[C]21 PWGAMUODYKBQLG-UHFFFAOYSA-N 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical group C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003003 spiro group Chemical group 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- 125000005578 chrysene group Chemical group 0.000 claims description 4
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 150000004002 naphthaldehydes Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 91
- 230000015572 biosynthetic process Effects 0.000 description 49
- 238000003786 synthesis reaction Methods 0.000 description 48
- 230000032258 transport Effects 0.000 description 43
- LYBVNBMFAXCOOD-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=C(N=N1)C1=CC=C(C=C1)B(O)O Chemical compound C1(=CC=CC=C1)C1=CC=C(N=N1)C1=CC=C(C=C1)B(O)O LYBVNBMFAXCOOD-UHFFFAOYSA-N 0.000 description 28
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 238000002474 experimental method Methods 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 238000000034 method Methods 0.000 description 14
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 13
- 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 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 125000006267 biphenyl group Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000002002 slurry Substances 0.000 description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000005580 triphenylene group Chemical group 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- JKHCVYDYGWHIFJ-UHFFFAOYSA-N Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 Chemical compound Clc1nc(nc(n1)-c1ccc(cc1)-c1ccccc1)-c1ccccc1 JKHCVYDYGWHIFJ-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- XJIPTTLNJAQLLR-UHFFFAOYSA-N 2-bromonaphthalene-1-carbaldehyde Chemical compound C1=CC=CC2=C(C=O)C(Br)=CC=C21 XJIPTTLNJAQLLR-UHFFFAOYSA-N 0.000 description 5
- JWWMUTCXVNBWGP-UHFFFAOYSA-N 4-chloro-2-phenyl-6-(4-phenylphenyl)pyrimidine Chemical compound C1(=CC=C(C=C1)C1=NC(=NC(=C1)Cl)C1=CC=CC=C1)C1=CC=CC=C1 JWWMUTCXVNBWGP-UHFFFAOYSA-N 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- XRJUVKFVUBGLMG-UHFFFAOYSA-N naphtho[1,2-e][1]benzothiole Chemical group C1=CC=CC2=C3C(C=CS4)=C4C=CC3=CC=C21 XRJUVKFVUBGLMG-UHFFFAOYSA-N 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- HMWTUKNXEQNLCK-UHFFFAOYSA-N O1C=CC=C1.C1(=CC=CC2=CC=C3C(=C12)C=CC=C3)C=O Chemical class O1C=CC=C1.C1(=CC=CC2=CC=C3C(=C12)C=CC=C3)C=O HMWTUKNXEQNLCK-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000001110 calcium chloride Substances 0.000 description 4
- 229910001628 calcium chloride Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 150000001716 carbazoles Chemical group 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- NYESPUIMUJRIAP-UHFFFAOYSA-N naphtho[1,2-e][1]benzofuran Chemical group C1=CC=CC2=C3C(C=CO4)=C4C=CC3=CC=C21 NYESPUIMUJRIAP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 2
- ZWHOTPNCEFWATE-CQSZACIVSA-N (3R)-3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylpyrrolidine-1-carboxamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)O[C@H]1CN(CC1)C(=O)NC1=CC=CC=C1 ZWHOTPNCEFWATE-CQSZACIVSA-N 0.000 description 2
- CPFALCJMNUHBHP-UHFFFAOYSA-N (9,9-diphenylfluoren-2-yl)boronic acid Chemical compound C12=CC(B(O)O)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 CPFALCJMNUHBHP-UHFFFAOYSA-N 0.000 description 2
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 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 2
- ZYNCORRXECPABC-UHFFFAOYSA-N 17-chlorospiro[1-azapentacyclo[10.7.1.02,7.08,20.014,19]icosa-2,4,6,8(20),9,11,14(19),15,17-nonaene-13,9'-fluorene] Chemical compound ClC1=CC2=C(C=C1)C1(C3=C(C=CC=C3)C3=C1C=CC=C3)C1=C3N2C2=C(C=CC=C2)C3=CC=C1 ZYNCORRXECPABC-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- BVKRPQCDGACLPX-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyindol-1-yl]-N-methyl-N-phenylacetamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC1=C2C=CN(C2=CC=C1)CC(=O)N(C1=CC=CC=C1)C BVKRPQCDGACLPX-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- 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 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- MROVZCRMXJZHCN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-(2-hydroxyethyl)benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCCO)C=CC=1 MROVZCRMXJZHCN-UHFFFAOYSA-N 0.000 description 2
- NRLQBVLOUUPAMI-UHFFFAOYSA-N 8-[3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxybenzoyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)N2CCC3(CNC(O3)=O)CC2)C=CC=1 NRLQBVLOUUPAMI-UHFFFAOYSA-N 0.000 description 2
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 2
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 2
- LJHFUFVRZNYVMK-ZDUSSCGKSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[(3S)-3-hydroxypyrrolidin-1-yl]methanone Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C=CC=1)C(=O)N1C[C@H](CC1)O LJHFUFVRZNYVMK-ZDUSSCGKSA-N 0.000 description 2
- KDSYNTPPPISIJB-UHFFFAOYSA-N [3-[[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxymethyl]phenyl]-(3-fluoro-4-hydroxypyrrolidin-1-yl)methanone Chemical compound NCc1cc(OCc2cccc(c2)C(=O)N2CC(O)C(F)C2)nc(c1)C(F)(F)F KDSYNTPPPISIJB-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
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- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical compound C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 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
- 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
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- 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
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- XNUVVHVFAAQPQY-UHFFFAOYSA-L manganese(2+) quinolin-8-olate Chemical compound N1=CC=CC2=CC=CC(=C12)[O-].[Mn+2].N1=CC=CC2=CC=CC(=C12)[O-] XNUVVHVFAAQPQY-UHFFFAOYSA-L 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 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
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 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
- 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
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010992 reflux 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- UPIADLCYNMJMKP-UHFFFAOYSA-N spiro[1-azapentacyclo[10.7.1.02,7.08,20.014,19]icosa-2,4,6,8(20),9,11,14,16,18-nonaene-13,9'-fluorene]-2'-ylboronic acid Chemical compound C12=CC=CC=C2C2=CC=CC3=C2N1C1=CC=CC=C1C31C2=CC=CC=C2C2=CC=C(B(O)O)C=C21 UPIADLCYNMJMKP-UHFFFAOYSA-N 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 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
- 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
- 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 1
- KWQNQSDKCINQQP-UHFFFAOYSA-K tri(quinolin-8-yloxy)gallane Chemical compound C1=CN=C2C(O[Ga](OC=3C4=NC=CC=C4C=CC=3)OC=3C4=NC=CC=C4C=CC=3)=CC=CC2=C1 KWQNQSDKCINQQP-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000004506 ultrasonic cleaning Methods 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
- 239000008096 xylene Substances 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
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/81—Anodes
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
- H10K50/82—Cathodes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Description
前記有機物層は、発光層を含み、
前記有機物層は、前記発光層および陰極の間に備えられた電子調節層および電子輸送層をさらに含み、
前記電子調節層は、下記化学式1で表される化合物を含み、
前記電子輸送層は、下記化学式11で表される化合物を含むものである有機発光素子を提供する。
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
L1は、下記化学式2〜5のうちのいずれか1つで表され、
[化学式2]
[化学式4]
点線
S1〜S4は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
pおよびqは、互いに同一または異なり、それぞれ独立に、0〜6の整数であり、
rは、0〜8の整数であり、
yは、0〜4の整数であり、
p、q、rおよびyがそれぞれ2以上の整数の時、複数のS1〜S4それぞれは、互いに同一または異なり、
L2は、直接結合;または置換もしくは非置換のアリーレン基であり、
Ar3は、L1が化学式2〜4の場合に、置換もしくは非置換のアリール基;SまたはOを含む置換もしくは非置換のヘテロ環基;置換もしくは非置換のカルバゾール基;または下記化学式6〜10のうちのいずれか1つで表され、
Ar3は、L1が化学式5の場合に、置換もしくは非置換のアリール基;SまたはOを含む置換もしくは非置換のヘテロ環基;または下記化学式6〜10のうちのいずれか1つで表され、
[化学式6]
[化学式10]
X1は、O、S、またはNRであり、
X2〜X6のうちの少なくとも2つは、Nであり、残りは、それぞれ独立に、CR'であり、
前記RおよびR'は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、
R1〜R6、R9およびR10は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
Y1〜Y4のうちの少なくとも1つは、Nであり、残りは、CR"であり、
前記R"は、それぞれ独立に、水素または重水素であり、
R7およびR8は、直接結合するか、互いに結合して置換もしくは非置換の環を形成し、
m、n、t、u、vおよびxはそれぞれ、0〜4の整数であり、wは、0〜3の整数であり、m、n、t、u、v、wおよびxがそれぞれ2以上の整数の時、複数のR1〜R6、R9およびR10はそれぞれ、互いに同一または異なり、
sは、0〜2の整数であり、sが2の時、2個のR3は、互いに同一または異なり、
[化学式11]
前記R"'は、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、
Ar4〜Ar6は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
L3は、直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
lは、1または2であり、lが2の場合、Ar6は、互いに同一または異なる。
前記有機物層は、発光層を含み、
前記有機物層は、前記発光層および陰極の間に備えられた電子調節層および電子輸送層をさらに含み、
前記電子調節層は、上記化学式1で表される化合物を含み、
前記電子輸送層は、上記化学式11で表される化合物を含むものである有機発光素子を提供する。
前記Ar3は、L1が化学式5の場合に、置換されたフェニル基;置換もしくは非置換のフルオレニル基;置換もしくは非置換のベンゾフルオレニル基;置換もしくは非置換のビスピロフルオレニル基;置換もしくは非置換のスピロフルオレンインデノフェナントレン基;置換もしくは非置換のジスピロフルオレンアントラセンフルオレン基;置換もしくは非置換のトリフェニレン基;SまたはOを含むC4〜C20のヘテロ環基;または前記化学式6〜10のうちのいずれか1つで表される。
前記Ar3は、L1が化学式5の場合に、置換されたフェニル基;置換もしくは非置換のフルオレニル基;置換もしくは非置換のベンゾフルオレニル基;置換もしくは非置換のスピロビフルオレニル基;置換もしくは非置換のスピロフルオレンインデノフェナントレン基;置換もしくは非置換のジスピロフルオレンアントラセンフルオレン基;置換もしくは非置換のトリフェニレン基;置換もしくは非置換のピリミジル基;置換もしくは非置換のピリダジニル基;置換もしくは非置換のトリアジニル基;置換もしくは非置換のベンゾカルバゾリル基;置換もしくは非置換のベンズイミダゾール基;置換もしくは非置換のベンズオキサゾール基;置換もしくは非置換のベンゾチアゾール基;置換もしくは非置換のジベンゾフラン基;置換もしくは非置換のジベンゾチオフェン基;置換もしくは非置換のベンゾナフトフラン基;または置換もしくは非置換のベンゾナフトチオフェン基であり、
前記「置換もしくは非置換の」とは、重水素;ハロゲン基;シアノ基;C1〜C10のアルキル基;およびC6〜C10のアリール基の中から選択される少なくとも1つで置換もしくは非置換であることを意味する。
前記Ar3は、L1が化学式5の場合に、置換されたフェニル基;置換もしくは非置換のフルオレニル基;置換もしくは非置換のベンゾフルオレニル基;置換もしくは非置換のスピロビフルオレニル基;置換もしくは非置換のスピロフルオレンインデノフェナントレン基;置換もしくは非置換のジスピロフルオレンアントラセンフルオレン基;置換もしくは非置換のトリフェニレン基;置換もしくは非置換のピリミジル基;置換もしくは非置換のピリダジニル基;置換もしくは非置換のトリアジニル基;置換もしくは非置換のベンゾカルバゾリル基;置換もしくは非置換のベンズイミダゾール基;置換もしくは非置換のベンズオキサゾール基;置換もしくは非置換のベンゾチアゾール基;置換もしくは非置換のジベンゾフラン基;置換もしくは非置換のジベンゾチオフェン基;置換もしくは非置換のベンゾナフトフラン基;または置換もしくは非置換のベンゾナフトチオフェン基であり、
前記「置換もしくは非置換の」とは、シアノ基;メチル基;エチル基;フェニル基;またはビフェニル基で置換もしくは非置換であることを意味する。
前記Ar3は、L1が化学式5の場合に、シアノ基で置換されたフェニル基;シアノ基、アルキル基、またはアリール基で置換もしくは非置換のフルオレニル基;アルキル基またはアリール基で置換もしくは非置換のベンゾフルオレニル基;スピロビフルオレニル基;スピロフルオレンインデノフェナントレン基;ジスピロフルオレンアントラセンフルオレン基;トリフェニレン基;ピリミジル基;ピリダジニル基;フェニル基で置換もしくは非置換のトリアジニル基;ベンゾカルバゾリル基;ベンズイミダゾール基;ベンズオキサゾール基;ベンゾチアゾール基;ジベンゾフラン基;ジベンゾチオフェン基;ベンゾナフトフラン基;またはベンゾナフトチオフェン基である。
[化学式6−2−2]
[化学式7−3]
[化学式9−4]
[化学式10−2]
n1は、1以上の整数であり、
Ar10は、置換もしくは非置換の1価以上のベンゾフルオレン基;置換もしくは非置換の1価以上のフルオランテン基;置換もしくは非置換の1価以上のピレン基;または置換もしくは非置換の1価以上のクリセン基であり、
L10は、直接結合;置換もしくは非置換のアリーレン基;置換もしくは非置換のヘテロアリーレン基であり、
Ar11およびAr12は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;置換もしくは非置換のシリル基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリールアルキル基;または置換もしくは非置換のヘテロ環基であるか、互いに結合して置換もしくは非置換の環を形成してもよいし、
n1が2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。
Ar13およびAr14は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基であり、
G1〜G8は、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基である。
201:陽極
301:発光層
401:電子調節層
501:電子輸送層
601:陰極
Claims (16)
- 陽極と、前記陽極に対向して備えられた陰極と、前記陽極と前記陰極との間に有機物層とを含む有機発光素子であって、
前記有機物層は、発光層を含み、
前記有機物層は、前記発光層および陰極の間に備えられた電子調節層および電子輸送層をさらに含み、
前記電子調節層は、下記の化学式1で表される化合物を含み、
前記電子輸送層は、下記の化学式11で表される化合物を含む、
有機発光素子:
[化学式1]
Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
L1は、下記の化学式2〜5のうちのいずれか1つで表され、
[化学式2]
点線
S1〜S4は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
pおよびqは、互いに同一または異なり、それぞれ独立に、0〜6の整数であり、
rは、0〜8の整数であり、
yは、0〜4の整数であり、
p、q、rおよびyがそれぞれ、2以上の整数の時、複数のS1〜S4それぞれは、互いに同一または異なり、
L2は、直接結合;または置換もしくは非置換のアリーレン基であり、
前記Ar 3 は、L 1 が化学式2〜4の場合に、シアノ基で置換されたフェニル基;置換もしくは非置換のフルオレニル基;置換もしくは非置換のベンゾフルオレニル基;置換もしくは非置換のスピロビフルオレニル基;置換もしくは非置換のスピロフルオレンインデノフェナントレン基;置換もしくは非置換のジスピロフルオレンアントラセンフルオレン基;SまたはOを含むC 4 〜C 20 のヘテロ環基;アリール基で置換されたカルバゾール基;または化学式6〜10のうちのいずれか1つで表され、
前記Ar 3 は、L 1 が化学式5の場合に、シアノ基で置換されたフェニル基;置換もしくは非置換のフルオレニル基;置換もしくは非置換のベンゾフルオレニル基;置換もしくは非置換のスピロビフルオレニル基;置換もしくは非置換のスピロフルオレンインデノフェナントレン基;置換もしくは非置換のジスピロフルオレンアントラセンフルオレン基;SまたはOを含むC 4 〜C 20 のヘテロ環基;または化学式6〜10のうちのいずれか1つで表され、
[化学式6]
X1は、O、SまたはNRであり、
X2〜X6のうちの少なくとも2つは、Nであり、残りは、それぞれ独立に、CR'であり、
前記RおよびR'は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、
R1〜R6、R9およびR10は、互いに同一または異なり、それぞれ独立に、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
Y1〜Y4のうちの少なくとも1つは、Nであり、残りは、CR"であり、
前記R"は、それぞれ独立に、水素または重水素であり、
R7およびR8は、直接結合するか、互いに結合して置換もしくは非置換の環を形成し、
m、n、t、u、vおよびxはそれぞれ、0〜4の整数であり、wは、0〜3の整数であり、m、n、t、u、v、wおよびxがそれぞれ2以上の整数の時、複数のR1〜R6、R9およびR10はそれぞれ、互いに同一または異なり、
sは、0〜2の整数であり、sが2の時、2個のR3は、互いに同一または異なり、
前記化学式10の結合する部分は、R6、R9、R10またはR7およびR8が結合して形成される環と結合され、
[化学式11]
前記R"'は、水素;重水素;ハロゲン基;置換もしくは非置換のアルキル基;または置換もしくは非置換のアリール基であり、
Ar4〜Ar6は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;または置換もしくは非置換のヘテロ環基であり、
L3は、直接結合;置換もしくは非置換のアリーレン基;または置換もしくは非置換の2価のヘテロ環基であり、
lは、1または2であり、lが2の場合、Ar6は、互いに同一または異なる。 - 前記L2は、直接結合;または置換もしくは非置換のC6〜C20のアリーレン基である、
請求項1に記載の有機発光素子。 - 前記Ar3は、L1が化学式2〜4の場合に、シアノ基で置換されたフェニル基;置換もしくは非置換のフルオレニル基;置換もしくは非置換のベンゾフルオレニル基;置換もしくは非置換のスピロビフルオレニル基;置換もしくは非置換のスピロフルオレンインデノフェナントレン基;置換もしくは非置換のジスピロフルオレンアントラセンフルオレン基;アリール基で置換されたカルバゾール基;置換もしくは非置換のピリミジル基;置換もしくは非置換のピリダジニル基;置換もしくは非置換のトリアジニル基;置換もしくは非置換のベンゾカルバゾリル基;置換もしくは非置換のベンズイミダゾール基;ベンズオキサゾール基;ベンゾチアゾール基;ジベンゾフラン基;ジベンゾチオフェン基;ベンゾナフトフラン基;またはベンゾナフトチオフェン基であり、
Ar3は、L1が化学式5の場合に、シアノ基で置換されたフェニル基;置換もしくは非置換のフルオレニル基;置換もしくは非置換のベンゾフルオレニル基;置換もしくは非置換のスピロビフルオレニル基;置換もしくは非置換のスピロフルオレンインデノフェナントレン基;置換もしくは非置換のジスピロフルオレンアントラセンフルオレン基;置換もしくは非置換のピリミジル基;置換もしくは非置換のピリダジニル基;置換もしくは非置換のトリアジニル基;置換もしくは非置換のベンゾカルバゾリル基;置換もしくは非置換のベンズイミダゾール基;ベンズオキサゾール基;ベンゾチアゾール基;ジベンゾフラン基;ジベンゾチオフェン基;ベンゾナフトフラン基;またはベンゾナフトチオフェン基である、
請求項1または2に記載の有機発光素子。 - 前記Ar1およびAr2は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のC6〜C20のアリール基である、
請求項1から3のいずれか一項に記載の有機発光素子。 - 前記S1〜S4は、水素である、
請求項1から4のいずれか一項に記載の有機発光素子。 - 前記R1〜R6およびR9〜R10は、水素である、
請求項1から5のいずれか一項に記載の有機発光素子。 - 前記化学式1で表される化合物は、下記構造式の中から選択されるいずれか1つである、
請求項1から6のいずれか一項に記載の有機発光素子:
- 前記Ar4およびAr5は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のC6〜C20のアリール基である、
請求項1から7のいずれか一項に記載の有機発光素子。 - 前記L3は、直接結合;または置換もしくは非置換のC6〜C20のアリーレン基である、
請求項1から8のいずれか一項に記載の有機発光素子。 - 前記Ar6は、置換もしくは非置換のスピロフルオレンインドロアクリジン基;置換もしくは非置換のインドロカルバゾール基;置換もしくは非置換のベンゾカルバゾール基;置換もしくは非置換のカルバゾール基;置換もしくは非置換のスピロビフルオレニル基;または置換もしくは非置換のフルオレニル基である、
請求項1から9のいずれか一項に記載の有機発光素子。 - 前記化学式11で表される化合物は、下記構造式の中から選択されるいずれか1つである、
請求項1から10のいずれか一項に記載の有機発光素子:
- 前記電子調節層は、発光層と電子輸送層との間に備えられた、
請求項1から11のいずれか一項に記載の有機発光素子。 - 前記有機発光素子は、正孔注入層、正孔輸送層、発光層、電子注入層、電子阻止層、および正孔阻止層からなる群より選択される1層または2層以上をさらに含む、
請求項1から12のいずれか一項に記載の有機発光素子。 - 前記有機物層は、発光層を含み、
前記発光層は、下記の化学式A−1の化合物を含む、
請求項1から13のいずれか一項に記載の有機発光素子:
[化学式A−1]
n1は、1以上の整数であり、
Ar10は、置換もしくは非置換の1価以上のベンゾフルオレン基;置換もしくは非置換の1価以上のフルオランテン基;置換もしくは非置換の1価以上のピレン基;または置換もしくは非置換の1価以上のクリセン基であり、
L10は、直接結合;置換もしくは非置換のアリーレン基;置換もしくは非置換のヘテロアリーレン基であり、
Ar11およびAr12は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換のアリール基;置換もしくは非置換のシリル基;置換もしくは非置換のアルキル基;置換もしくは非置換のアリールアルキル基;または置換もしくは非置換のヘテロ環基であるか、互いに結合して置換もしくは非置換の環を形成してもよいし、
n1が2以上の場合、2以上の括弧内の構造は、互いに同一または異なる。 - 前記有機物層は、発光層を含み、前記発光層は、下記の化学式A−2で表される化合物を含む、
請求項1から14のいずれか一項に記載の有機発光素子:
[化学式A−2]
Ar13およびAr14は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基であり、
G1〜G8は、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基である。 - 前記発光層は、下記の化学式A−2で表される化合物を含む、
請求項14に記載の有機発光素子:
[化学式A−2]
Ar13およびAr14は、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基であり、
G1〜G8は、互いに同一または異なり、それぞれ独立に、水素;置換もしくは非置換の単環のアリール基;または置換もしくは非置換の多環のアリール基である。
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