JP5746701B2 - 有機発光ダイオード発光層のための化合物 - Google Patents
有機発光ダイオード発光層のための化合物 Download PDFInfo
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- JP5746701B2 JP5746701B2 JP2012529887A JP2012529887A JP5746701B2 JP 5746701 B2 JP5746701 B2 JP 5746701B2 JP 2012529887 A JP2012529887 A JP 2012529887A JP 2012529887 A JP2012529887 A JP 2012529887A JP 5746701 B2 JP5746701 B2 JP 5746701B2
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- Japan
- Prior art keywords
- optionally substituted
- light emitting
- alkyl
- phenyl
- mmol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 title claims description 45
- 239000010410 layer Substances 0.000 description 90
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- 125000000217 alkyl group Chemical group 0.000 description 67
- 125000001424 substituent group Chemical group 0.000 description 55
- -1 Benzoimidazol-2-yl Chemical group 0.000 description 53
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000463 material Substances 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 31
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- 125000003545 alkoxy group Chemical group 0.000 description 28
- 229910052799 carbon Inorganic materials 0.000 description 28
- 125000003118 aryl group Chemical group 0.000 description 26
- 239000007787 solid Substances 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- 125000002252 acyl group Chemical group 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 125000004093 cyano group Chemical group *C#N 0.000 description 16
- 125000005843 halogen group Chemical group 0.000 description 16
- 229910052786 argon Inorganic materials 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
- 230000000903 blocking effect Effects 0.000 description 13
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 13
- 239000012948 isocyanate Substances 0.000 description 13
- 150000002513 isocyanates Chemical class 0.000 description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 13
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- 125000001188 haloalkyl group Chemical group 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 7
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 7
- 239000000956 alloy Substances 0.000 description 7
- 229910045601 alloy Inorganic materials 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 6
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001716 carbazoles Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- PEYQCEFPKMIOFP-UHFFFAOYSA-N 1-phenyl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzimidazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)C=C1 PEYQCEFPKMIOFP-UHFFFAOYSA-N 0.000 description 5
- ZLCMXHALWTYHOY-UHFFFAOYSA-N 3,6-dibromo-9-(4-methylphenyl)carbazole Chemical compound C1=CC(C)=CC=C1N1C2=CC=C(Br)C=C2C2=CC(Br)=CC=C21 ZLCMXHALWTYHOY-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 5
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 5
- 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 4
- FQIRBKKYMJKENC-UHFFFAOYSA-N 2-(4-bromophenyl)-1,3-benzothiazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2S1 FQIRBKKYMJKENC-UHFFFAOYSA-N 0.000 description 4
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 4
- 229920000144 PEDOT:PSS Polymers 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 4
- IUFDZNVMARBLOJ-UHFFFAOYSA-K aluminum;quinoline-2-carboxylate Chemical compound [Al+3].C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IUFDZNVMARBLOJ-UHFFFAOYSA-K 0.000 description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- 238000001194 electroluminescence spectrum Methods 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- XBOVCCFGAJIZHG-UHFFFAOYSA-N 2-(2-bromophenyl)-1-phenylbenzimidazole Chemical compound BrC1=CC=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XBOVCCFGAJIZHG-UHFFFAOYSA-N 0.000 description 3
- DXRLALXPCIOIDK-UHFFFAOYSA-N 2-(4-bromophenyl)-1-phenylbenzimidazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 DXRLALXPCIOIDK-UHFFFAOYSA-N 0.000 description 3
- JHXCWPKYKVFZCG-UHFFFAOYSA-N 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzothiazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2SC3=CC=CC=C3N=2)C=C1 JHXCWPKYKVFZCG-UHFFFAOYSA-N 0.000 description 3
- DENKGPBHLYFNGK-UHFFFAOYSA-N 4-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Br)C=C1 DENKGPBHLYFNGK-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- GYFSBCDGBBWMBE-UHFFFAOYSA-N [9-(4-methylphenyl)carbazol-3-yl]boronic acid Chemical compound C1=CC(C)=CC=C1N1C2=CC=C(B(O)O)C=C2C2=CC=CC=C21 GYFSBCDGBBWMBE-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000004438 haloalkoxy group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- NGTOTQREGFJSJL-UHFFFAOYSA-N n-(2-anilinophenyl)-2-bromobenzamide Chemical compound BrC1=CC=CC=C1C(=O)NC1=CC=CC=C1NC1=CC=CC=C1 NGTOTQREGFJSJL-UHFFFAOYSA-N 0.000 description 3
- JUPGVNFYCQXVSQ-UHFFFAOYSA-N n-(2-anilinophenyl)-4-bromobenzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NC1=CC=CC=C1NC1=CC=CC=C1 JUPGVNFYCQXVSQ-UHFFFAOYSA-N 0.000 description 3
- 235000011056 potassium acetate Nutrition 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 2
- RBVHJNZMSBQFDK-UHFFFAOYSA-N 2-(4-bromophenyl)-1,3-benzoxazole Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2O1 RBVHJNZMSBQFDK-UHFFFAOYSA-N 0.000 description 2
- BAEPPSMSKKCZGG-UHFFFAOYSA-N 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3-benzoxazole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 BAEPPSMSKKCZGG-UHFFFAOYSA-N 0.000 description 2
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 2
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 2
- YACSIMLPPDISOJ-UHFFFAOYSA-N 4-(4-anilinophenyl)-3-(3-methylphenyl)-n-phenylaniline Chemical compound CC1=CC=CC(C=2C(=CC=C(NC=3C=CC=CC=3)C=2)C=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 YACSIMLPPDISOJ-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 Cc1c2-c3c(*)c(*)c(*)c(*)c3*(*)c2c(*=*)c(*)c1** Chemical compound Cc1c2-c3c(*)c(*)c(*)c(*)c3*(*)c2c(*=*)c(*)c1** 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JWZDGRQEYVKVGH-UHFFFAOYSA-N [6-borono-9-(4-methylphenyl)carbazol-3-yl]boronic acid Chemical compound C1=CC(C)=CC=C1N1C2=CC=C(B(O)O)C=C2C2=CC(B(O)O)=CC=C21 JWZDGRQEYVKVGH-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XEPMXWGXLQIFJN-UHFFFAOYSA-K aluminum;2-carboxyquinolin-8-olate Chemical compound [Al+3].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 XEPMXWGXLQIFJN-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000004986 diarylamino group Chemical group 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000003187 heptyl group Chemical class [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 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 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 2
- 239000012071 phase Substances 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
-
- 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
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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Description
本願は、2009年9月16日に出願された米国仮特許出願第61/242897号の利益を主張し、この仮特許出願は参照によりそのすべてが本明細書に組み込まれる。
本明細書に開示する実施形態は、有機発光素子の発光性材料用の両極性ホストなどといった有機発光ダイオード材料において役立ちうる化合物に関する。
白色有機発光素子(WOLED)は、バックライト光源、フルカラーディスプレイとしての、また一般照明目的への、それらの潜在的応用ゆえに、多くの注目を集め、活発に研究されてきた。白色光を生み出すためのさまざまな素子構成のなかでも、単一の発光層を持つ素子は、それらの素子製作および加工の平易さゆえに、多くの注目を集めてきた。数多くの既存の単一発光層タイプのうち、リン光材料を適当なホスト材料と組み合わせて使用する素子(全リン光型)と、青色蛍光ホストを黄色リン光発光体と共に使用する素子は、特に注目を集めてきた。これらは、いくつかの理由から、他のタイプの素子よりも効果的でありうる。例えば、リン光発光体は一重項励起と三重項励起の両方を得ることができ、したがって100%の内部量子効率を達成する可能性を有しうる。もう1つの重要な事項は、ホスト材料の添加が発光性材料の濃度消光を減少させうるだけでなく、発光性材料はホスト材料より高価であるだろうから、素子の総原価も低下させうることである。また、単層素子の製作は多層素子よりもはるかに容易であり、費用対効果も大きいだろう。
によって表される化合物を提供する。
別段の表示がない限り、アルキルまたはアリールなどの化学構造的特徴を指して「置換されていてもよい」という場合、それは、その特徴が、置換基を持たなくても(すなわち無置換でも)よいし、1つ以上の置換基を持っていてもよいことを意味する。「置換され」ている特徴は、1つ以上の置換基を有する。用語「置換基」は当業者に知られている通常の意味を有する。一部の実施形態において、置換基は、約500g/m未満、約300g/m未満、約200g/m未満、約100g/m未満、または約50g/m未満の分子量(例えば置換基の原子の原子質量の和)を有しうる、当技術分野において知られている通常の有機部分であることができる。一部の実施形態において、置換基は、0〜30個、0〜20個、0〜10個、または0〜5個の炭素原子と、N、O、S、Si、F、Cl、Br、またはIから独立して選択される0〜30個、0〜20個、0〜10個、または0〜5個のヘテロ原子とを含む(ただし置換基は、C、N、O、S、Si、F、Cl、Br、またはIから選択される少なくとも1つの原子を含むものとする)。置換基の例には、アルキル、アルケニル、アルキニル、置換されていてもよいカルバゾリル、置換されていてもよいアリール、置換されていてもよいジアリールアミノ、置換されていてもよいヘテロアリール、ヘテロアリシクリル、アラルキル、ヘテロアラルキル、(ヘテロアリシクリル)アルキル、ヒドロキシ、保護ヒドロキシ、アルコキシ、アリールオキシ、アシル、エステル、メルカプト、アルキルチオ、アリールチオ、シアノ、ハロゲン、カルボニル、チオカルボニル、O−カルバミル、N−カルバミル、O−チオカルバミル、N−チオカルバミル、C−アミド、N−アミド、S−スルホンアミド、N−スルホンアミド、C−カルボキシ、保護C−カルボキシ、O−カルボキシ、イソシアナト、チオシアナト、イソチオシアナト、ニトロ、シリル、スルフェニル、スルフィニル、スルホニル、ハロヒドロカルビル、ハロアルキル、ハロアルコキシル、トリハロメタンスルホニル、トリハロメタンスルホンアミド、およびアミノ(1置換および2置換アミノ基を含む)、およびその保護誘導体などがあるが、これらに限るわけではない。
を指す。置換されていてもよい場合、置換基の付加は考えうる任意の位置で起こりうる。
によって表される化合物を提供する。一部の実施形態において、Aは、Cbの3位に結合することができ、存在しないか、Ph2またはPh2−Het2であることができる。AがPh2またはPh2−Het2であることができる実施形態において、Ph2はCbの3位に直接結合することができる。Ph1はCbの6位に結合することができ、Ar1はCbの9位に結合することができる。一部の実施形態において、置換されていてもよいカルバゾールは、C1−10アルキル(例えばC1−10直鎖アルキル、C3−10分枝アルキル、またはC3−10シクロアルキル)、C1−10アルコキシ、およびハロからなる群より独立して選択される0、1、2、3、または4個の置換基を有することができる。
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US24289709P | 2009-09-16 | 2009-09-16 | |
US61/242,897 | 2009-09-16 | ||
PCT/US2010/048990 WO2011034967A1 (en) | 2009-09-16 | 2010-09-15 | Compounds for organic light emitting diode emissive layers |
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EP (1) | EP2477979B1 (ja) |
JP (1) | JP5746701B2 (ja) |
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WO2011034967A1 (en) | 2009-09-16 | 2011-03-24 | Nitto Denko Corporation | Compounds for organic light emitting diode emissive layers |
TW201204811A (en) | 2010-07-19 | 2012-02-01 | Nitto Denko Corp | Phototherapy devices and methods comprising substituted carbazole compounds |
JP5949354B2 (ja) * | 2011-09-15 | 2016-07-06 | Jnc株式会社 | 電子受容性窒素含有へテロアリールを含む置換基を有するカルバゾール化合物および有機電界発光素子 |
US9299945B2 (en) | 2011-12-14 | 2016-03-29 | Nitto Denko Corporation | Top-emitting white organic light-emitting diodes having improved efficiency and stability |
WO2014039721A1 (en) | 2012-09-07 | 2014-03-13 | Nitto Denko Corporation | Top-emitting white organic light-emitting diodes having improved efficiency and stability |
CN102881830B (zh) * | 2012-09-28 | 2015-11-04 | 北京大学 | 一种有机太阳能电池及其制备方法 |
US9425408B2 (en) | 2013-03-22 | 2016-08-23 | Nitto Denko Corporation | Organic light emitting host materials |
CN103756670B (zh) | 2014-01-23 | 2015-12-09 | 上海和辉光电有限公司 | 有机电致发光材料及其制备方法和应用 |
CN104650043B (zh) * | 2014-07-08 | 2017-03-01 | 吉林奥来德光电材料股份有限公司 | 咪唑类电子传输材料及其制备方法和应用 |
CN104650044B (zh) * | 2014-08-15 | 2017-02-15 | 吉林奥来德光电材料股份有限公司 | 一种电子传输材料及其制备和器件 |
CN105646459A (zh) * | 2014-11-13 | 2016-06-08 | 上海和辉光电有限公司 | 一种化合物及其制备方法和应用 |
JP2018517289A (ja) * | 2015-05-29 | 2018-06-28 | ダウ グローバル テクノロジーズ エルエルシー | 有機組成物及び該組成物を含む有機層を備える電子デバイス |
CN111777602B (zh) * | 2020-08-11 | 2022-03-08 | 长春海谱润斯科技股份有限公司 | 一种含有咔唑的化合物及其有机电致发光器件 |
CN112851655B (zh) * | 2021-01-07 | 2022-09-02 | 山西华辉光电科技有限公司 | 一种基于咔唑的有机电致发光材料及其在器件中的应用 |
CN112778293B (zh) * | 2021-01-07 | 2022-05-24 | 山西华辉光电科技有限公司 | 有机电致磷光主体材料及其在有机电致发光器件中的应用 |
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JP5262081B2 (ja) | 2006-11-20 | 2013-08-14 | Jnc株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
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JP5479759B2 (ja) | 2008-09-05 | 2014-04-23 | 株式会社半導体エネルギー研究所 | ベンゾオキサゾール誘導体、発光素子用材料、発光素子、発光装置及び電子機器 |
WO2010044607A1 (en) | 2008-10-14 | 2010-04-22 | Cheil Industries Inc. | Benzimidazole compounds and organic photoelectric device with the same |
KR20110118646A (ko) | 2009-01-05 | 2011-10-31 | 플렉스트로닉스, 인크 | 유기 발광 다이오드 광선치료 조명 시스템 |
WO2011034967A1 (en) | 2009-09-16 | 2011-03-24 | Nitto Denko Corporation | Compounds for organic light emitting diode emissive layers |
TW201204811A (en) | 2010-07-19 | 2012-02-01 | Nitto Denko Corp | Phototherapy devices and methods comprising substituted carbazole compounds |
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US8586205B2 (en) | 2013-11-19 |
KR20120093879A (ko) | 2012-08-23 |
KR101810591B1 (ko) | 2017-12-20 |
EP2477979A1 (en) | 2012-07-25 |
JP2013505250A (ja) | 2013-02-14 |
CN102596939B (zh) | 2014-08-13 |
WO2011034967A1 (en) | 2011-03-24 |
CN102596939A (zh) | 2012-07-18 |
EP2477979B1 (en) | 2016-10-26 |
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