JP5479759B2 - 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 - Google Patents
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 Download PDFInfo
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- JP5479759B2 JP5479759B2 JP2009049170A JP2009049170A JP5479759B2 JP 5479759 B2 JP5479759 B2 JP 5479759B2 JP 2009049170 A JP2009049170 A JP 2009049170A JP 2009049170 A JP2009049170 A JP 2009049170A JP 5479759 B2 JP5479759 B2 JP 5479759B2
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- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title claims description 71
- 239000000463 material Substances 0.000 title claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
- 125000003003 spiro group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 298
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 204
- 239000000126 substance Substances 0.000 description 97
- 239000000243 solution Substances 0.000 description 59
- 150000001875 compounds Chemical class 0.000 description 54
- 239000000203 mixture Substances 0.000 description 51
- 238000000862 absorption spectrum Methods 0.000 description 48
- 239000000758 substrate Substances 0.000 description 48
- -1 benzoxazole compound Chemical class 0.000 description 47
- 230000015572 biosynthetic process Effects 0.000 description 46
- 238000003786 synthesis reaction Methods 0.000 description 46
- 239000010409 thin film Substances 0.000 description 43
- 238000005259 measurement Methods 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
- 230000005284 excitation Effects 0.000 description 39
- 238000000034 method Methods 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
- 239000000706 filtrate Substances 0.000 description 31
- 239000012046 mixed solvent Substances 0.000 description 31
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- 238000010521 absorption reaction Methods 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 238000002347 injection Methods 0.000 description 29
- 239000007924 injection Substances 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- 239000010453 quartz Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000000295 emission spectrum Methods 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 150000002894 organic compounds Chemical class 0.000 description 22
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- 238000000151 deposition Methods 0.000 description 19
- 238000001704 evaporation Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 238000006479 redox reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910045601 alloy Inorganic materials 0.000 description 15
- 239000000956 alloy Substances 0.000 description 15
- 239000011159 matrix material Substances 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000012298 atmosphere Substances 0.000 description 14
- 238000002484 cyclic voltammetry Methods 0.000 description 14
- 239000010408 film Substances 0.000 description 14
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 230000005281 excited state Effects 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
- 238000000746 purification Methods 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000000859 sublimation Methods 0.000 description 12
- 230000008022 sublimation Effects 0.000 description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- 239000002131 composite material Substances 0.000 description 11
- 238000001308 synthesis method Methods 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 10
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000004973 liquid crystal related substance Substances 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 238000004544 sputter deposition Methods 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 230000008021 deposition Effects 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- AZWHFTKIBIQKCA-UHFFFAOYSA-N [Sn+2]=O.[O-2].[In+3] Chemical compound [Sn+2]=O.[O-2].[In+3] AZWHFTKIBIQKCA-UHFFFAOYSA-N 0.000 description 7
- 229910052786 argon Inorganic materials 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- 230000000737 periodic effect Effects 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- FUESUFHXMQBDPR-UHFFFAOYSA-N 2-(4-carbazol-9-ylphenyl)-1,3-benzoxazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C1=NC2=CC=CC=C2O1 FUESUFHXMQBDPR-UHFFFAOYSA-N 0.000 description 6
- WNRSBDBOSTYWAH-UHFFFAOYSA-N 2-[4-(3,6-diphenylcarbazol-9-yl)phenyl]-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2OC3=CC=CC=C3N=2)C=2C3=CC(=CC=2)C=2C=CC=CC=2)C3=C1 WNRSBDBOSTYWAH-UHFFFAOYSA-N 0.000 description 6
- VDEKVUOMYZKWPO-UHFFFAOYSA-N 2-[4-(3-phenylcarbazol-9-yl)phenyl]-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2OC3=CC=CC=C3N=2)C=2C3=CC=CC=2)C3=C1 VDEKVUOMYZKWPO-UHFFFAOYSA-N 0.000 description 6
- JDJZLSOVHYQMKA-UHFFFAOYSA-N 2-[4-(4-carbazol-9-ylphenyl)phenyl]-1,3-benzoxazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C(C=C1)=CC=C1C(C=C1)=CC=C1C1=NC2=CC=CC=C2O1 JDJZLSOVHYQMKA-UHFFFAOYSA-N 0.000 description 6
- VFXRSWDYLTYPKM-UHFFFAOYSA-N 2-[4-(9-phenylcarbazol-3-yl)phenyl]-1,3-benzoxazole Chemical compound C1=CC=CC=C1N1C2=CC=C(C=3C=CC(=CC=3)C=3OC4=CC=CC=C4N=3)C=C2C2=CC=CC=C21 VFXRSWDYLTYPKM-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 6
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 238000001420 photoelectron spectroscopy Methods 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 229910052814 silicon oxide Inorganic materials 0.000 description 6
- 238000005092 sublimation method Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 230000007704 transition Effects 0.000 description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 description 6
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 6
- JGAVTCVHDMOQTJ-UHFFFAOYSA-N (4-carbazol-9-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 JGAVTCVHDMOQTJ-UHFFFAOYSA-N 0.000 description 5
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 5
- GLRVAFAIWYHTEZ-UHFFFAOYSA-N 2-(4-iodophenyl)-1,3-benzoxazole Chemical compound C1=CC(I)=CC=C1C1=NC2=CC=CC=C2O1 GLRVAFAIWYHTEZ-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 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 4
- 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 4
- 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 4
- KVTWQFQAJWSCPC-UHFFFAOYSA-N 2-[4-(6,9-diphenylcarbazol-3-yl)phenyl]-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC(=CC=2)C=2C=CC(=CC=2)C=2OC4=CC=CC=C4N=2)C3=C1 KVTWQFQAJWSCPC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052792 caesium Inorganic materials 0.000 description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010549 co-Evaporation Methods 0.000 description 4
- 239000007850 fluorescent dye Substances 0.000 description 4
- 229910003437 indium oxide Inorganic materials 0.000 description 4
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 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 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 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 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 3
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 3
- NJAKCIUOTIPYED-UHFFFAOYSA-N 4-iodobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(I)C=C1 NJAKCIUOTIPYED-UHFFFAOYSA-N 0.000 description 3
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- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
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- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
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Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
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| JP2009049170A JP5479759B2 (ja) | 2008-09-05 | 2009-03-03 | 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 |
| KR1020090082580A KR101670036B1 (ko) | 2008-09-05 | 2009-09-02 | 벤조옥사졸 유도체, 벤조옥사졸 유도체를 이용한 발광소자, 발광장치 및 전자기기 |
| TW098129715A TWI464163B (zh) | 2008-09-05 | 2009-09-03 | 苯并唑衍生物，以及使用苯并唑衍生物的發光元件、發光裝置與電子裝置 |
| US12/553,290 US8093399B2 (en) | 2008-09-05 | 2009-09-03 | Benzoxazole derivative, and light-emitting element, light-emitting device, and electronic device using benzoxazole derivative |
| US13/345,104 US8735597B2 (en) | 2008-09-05 | 2012-01-06 | Benzoxazole derivative, and light-emitting element, light-emitting device, and electronic device using benzoxazole derivative |
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| JP2008228252 | 2008-09-05 | ||
| JP2008228252 | 2008-09-05 | ||
| JP2009049170A JP5479759B2 (ja) | 2008-09-05 | 2009-03-03 | 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 |
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| JP2010083862A JP2010083862A (ja) | 2010-04-15 |
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| KR (1) | KR101670036B1 (OSRAM) |
| TW (1) | TWI464163B (OSRAM) |
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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 |
| US8329917B2 (en) | 2009-03-31 | 2012-12-11 | Semiconductor Energy Laboratory Co., Ltd. | Heterocyclic compound and light-emitting element, light-emitting device, lighting device, and electronic device using the same |
| JP5773585B2 (ja) * | 2009-06-29 | 2015-09-02 | 日東電工株式会社 | 発光性トリアリール |
| KR20120060817A (ko) | 2009-06-29 | 2012-06-12 | 닛토덴코 가부시키가이샤 | 발광 아릴-헤테로아릴 화합물 |
| US8586205B2 (en) * | 2009-09-16 | 2013-11-19 | Nitto Denko Corporation | Compounds for organic light emitting diode emissive layers |
| WO2012009283A1 (en) * | 2010-07-13 | 2012-01-19 | Nitto Denko Corporation | Phototherapy methods and devices comprising emissive aryl-heteroaryl compounds |
| WO2012012295A1 (en) * | 2010-07-19 | 2012-01-26 | Nitto Denko Corporation | Phototherapy devices and methods comprising substituted carbazole compounds |
| EP2428512B1 (en) * | 2010-09-08 | 2014-10-22 | Semiconductor Energy Laboratory Co., Ltd. | Fluorene compound, light-emitting element, light-emitting device, electronic device and lighting device |
| JP6031034B2 (ja) * | 2010-09-16 | 2016-11-24 | 日東電工株式会社 | 有機発光デバイスにおける使用のための置換型ビピリジン |
| JP5872861B2 (ja) * | 2010-11-30 | 2016-03-01 | 株式会社半導体エネルギー研究所 | カルバゾール化合物 |
| KR101910030B1 (ko) * | 2010-11-30 | 2018-10-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 벤조옥사졸 유도체, 발광 소자, 발광 장치, 전자기기 및 조명 장치 |
| US8426040B2 (en) | 2010-12-22 | 2013-04-23 | Nitto Denko Corporation | Compounds for use in light-emitting devices |
| KR20140020873A (ko) * | 2011-01-27 | 2014-02-19 | 닛토덴코 가부시키가이샤 | 임의 치환된 테르페닐 및 쿠아테르페닐 화합물을 포함한 광선요법 디바이스 및 방법 |
| US8933243B2 (en) | 2011-06-22 | 2015-01-13 | Nitto Denko Corporation | Polyphenylene host compounds |
| US9353085B2 (en) * | 2011-08-26 | 2016-05-31 | E-Ray Optoelectronics Technology Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent devices using the same |
| 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 |
| US9328094B2 (en) | 2011-09-19 | 2016-05-03 | Nitto Denko Corporation | Substituted biaryl compounds for light-emitting devices |
| US8952364B2 (en) | 2011-11-10 | 2015-02-10 | Nitto Denko Corporation | Light-emitting devices comprising nanostructures |
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| EP2802594B1 (en) | 2012-01-12 | 2017-04-19 | UDC Ireland Limited | Metal complexes with dibenzo[f,h]quinoxalines |
| US20150087685A1 (en) * | 2012-04-13 | 2015-03-26 | Nitto Denko Corporation | Phototherapy Devices and Methods Comprising Optionally Substituted Quinquiesphenyl Compounds |
| JP6339071B2 (ja) * | 2012-07-23 | 2018-06-06 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
| US20150239880A1 (en) | 2012-08-30 | 2015-08-27 | Kyushu University National University Corp. | Light emitting material, compound, and organic light emitting device using the same |
| US9263681B2 (en) | 2012-12-10 | 2016-02-16 | Nitto Denko Corporation | Organic light emitting host materials |
| WO2014093361A1 (en) | 2012-12-10 | 2014-06-19 | Nitto Denko Corporation | Bipolar hosts for light emitting devices |
| US9614162B2 (en) | 2012-12-17 | 2017-04-04 | Nitto Denko Corporation | Light-emitting devices comprising emissive layer |
| WO2014207001A1 (en) * | 2013-06-27 | 2014-12-31 | Dsm Ip Assets B.V. | Process for producing 2-phenyl-1,3-benzoxazoles |
| 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 |
| JP6491315B2 (ja) | 2014-08-08 | 2019-03-27 | ユー・ディー・シー アイルランド リミテッド | 電界発光イミダゾキノキサリンカルベン金属錯体 |
| US10424746B2 (en) | 2014-11-18 | 2019-09-24 | Udc Ireland Limited | Pt- or Pd-carbene complexes for use in organic light emitting diodes |
| KR102684614B1 (ko) | 2015-12-21 | 2024-07-15 | 유디씨 아일랜드 리미티드 | 삼각형 리간드를 갖는 전이 금속 착체 및 ｏｌｅｄ에서의 이의 용도 |
| EP3483148B1 (en) | 2016-07-07 | 2023-08-23 | Hodogaya Chemical Co., Ltd. | Compound having benzazole ring structure and organic electroluminescent element |
| WO2019026728A1 (ja) | 2017-08-04 | 2019-02-07 | 保土谷化学工業株式会社 | ベンゾアゾール環構造を有する化合物を含有する有機エレクトロルミネッセンス素子 |
| CN111316462B (zh) | 2017-11-06 | 2023-04-18 | 保土谷化学工业株式会社 | 具有茚并咔唑环结构的化合物及有机电致发光元件 |
| KR102695099B1 (ko) | 2017-11-16 | 2024-08-14 | 호도가야 가가쿠 고교 가부시키가이샤 | 유기 일렉트로루미네선스 소자 |
| WO2019111844A1 (ja) | 2017-12-05 | 2019-06-13 | 保土谷化学工業株式会社 | アリールアミン化合物および有機エレクトロルミネッセンス素子 |
| KR102264792B1 (ko) * | 2018-09-21 | 2021-06-15 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
| WO2020060288A1 (ko) * | 2018-09-21 | 2020-03-26 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
| CN113195482B (zh) | 2019-02-13 | 2024-12-20 | 保土谷化学工业株式会社 | 具有苯并唑环结构的化合物及有机电致发光元件 |
| KR102080737B1 (ko) * | 2019-05-29 | 2020-02-24 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
| CN110483495B (zh) * | 2019-09-16 | 2020-04-28 | 长春海谱润斯科技有限公司 | 一种杂环化合物及其有机电致发光器件 |
| KR102853364B1 (ko) | 2019-09-30 | 2025-09-03 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 화합물 |
| CN111138424B (zh) * | 2019-12-30 | 2021-02-09 | 中山大学 | 一种含苯并恶唑和咔唑结构的二胺单体及其制备方法和应用 |
| KR102460493B1 (ko) * | 2020-12-04 | 2022-11-02 | (주)랩토 | 디벤조 5원고리 화합물 및 이를 포함한 유기전계발광소자 |
| WO2023048118A1 (ja) * | 2021-09-21 | 2023-03-30 | 保土谷化学工業株式会社 | 化合物および有機エレクトロルミネッセンス素子 |
| CN114933595B (zh) * | 2022-04-24 | 2024-04-30 | 长春工业大学 | 一种2-苯基苯并噁唑多刺激响应荧光材料及其制备方法 |
| KR20250173623A (ko) * | 2024-06-03 | 2025-12-11 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자장치 |
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| US6602619B2 (en) * | 2001-10-19 | 2003-08-05 | Lightronik Technology Inc. | Organic EL device |
| JP4427947B2 (ja) | 2002-11-18 | 2010-03-10 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子及び表示装置 |
| US7505122B2 (en) * | 2005-04-28 | 2009-03-17 | Semiconductor Energy Laboratory Co., Ltd. | Evaluation method and manufacturing method of light-emitting element material, manufacturing method of light-emitting element, light-emitting element, and light-emitting device and electric appliance having light-emitting element |
| EP1724852A3 (en) * | 2005-05-20 | 2010-01-27 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting element, light emitting device, and electronic device |
| KR101324758B1 (ko) * | 2005-07-14 | 2013-11-06 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 카르바졸 유도체, 및 그것을 사용하여 얻어진 발광소자용재료, 발광소자, 전자기기 |
| KR101540037B1 (ko) * | 2005-09-12 | 2015-07-29 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 퀴녹살린 유도체, 및 퀴녹살린 유도체를 사용한 발광소자, 발광장치, 전자 기기 |
| DE602007006766D1 (de) | 2006-02-08 | 2010-07-08 | Kodak Graphic Comm Gmbh | Vorläufer einer uv-empfindlichen lithographischen druckplatte mit benzoxazolderivat und analoga davon als sensibilisator |
| WO2008038607A1 (en) * | 2006-09-28 | 2008-04-03 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, and light emitting element, light emitting device, and electronic device using the anthracene derivative |
| CN101627487B (zh) * | 2007-02-21 | 2011-08-03 | 株式会社半导体能源研究所 | 发光元件，发光器件，电子器件和喹喔啉衍生物 |
| KR101564762B1 (ko) * | 2007-11-30 | 2015-10-30 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 퀴녹살린 유도체, 및 퀴녹살린 유도체를 사용한 발광 소자,발광 장치 및 전자 기기 |
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| KR101529062B1 (ko) | 2008-09-05 | 2015-06-16 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 유기 반도체 재료 및 이를 사용한 발광 소자, 발광 장치, 조명 장치 및 전자기기 |
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| US8735597B2 (en) | 2014-05-27 |
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| KR101670036B1 (ko) | 2016-10-27 |
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