JP2009298778A - 有機化合物、ベンゾオキサゾール誘導体、およびベンゾオキサゾール誘導体を用いた発光素子、発光装置並びに電子機器 - Google Patents
有機化合物、ベンゾオキサゾール誘導体、およびベンゾオキサゾール誘導体を用いた発光素子、発光装置並びに電子機器 Download PDFInfo
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- JP2009298778A JP2009298778A JP2009116194A JP2009116194A JP2009298778A JP 2009298778 A JP2009298778 A JP 2009298778A JP 2009116194 A JP2009116194 A JP 2009116194A JP 2009116194 A JP2009116194 A JP 2009116194A JP 2009298778 A JP2009298778 A JP 2009298778A
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- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title claims abstract description 97
- 150000002894 organic compounds Chemical class 0.000 title claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
- 150000002367 halogens Chemical class 0.000 claims abstract description 33
- 125000000732 arylene group Chemical group 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 15
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 63
- 229910052757 nitrogen Inorganic materials 0.000 claims description 63
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 5
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 239000000243 solution Substances 0.000 abstract description 67
- 238000002347 injection Methods 0.000 abstract description 31
- 239000007924 injection Substances 0.000 abstract description 31
- 239000010410 layer Substances 0.000 description 209
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 132
- 239000000126 substance Substances 0.000 description 104
- -1 biphenyl-4,4'-diyl Chemical group 0.000 description 77
- 239000000463 material Substances 0.000 description 70
- 238000003786 synthesis reaction Methods 0.000 description 66
- 230000015572 biosynthetic process Effects 0.000 description 65
- 150000001875 compounds Chemical class 0.000 description 61
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
- 239000000203 mixture Substances 0.000 description 58
- 239000000758 substrate Substances 0.000 description 57
- 238000005481 NMR spectroscopy Methods 0.000 description 51
- 239000007787 solid Substances 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
- 238000000034 method Methods 0.000 description 37
- 239000010409 thin film Substances 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000000862 absorption spectrum Methods 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000010408 film Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- 230000005525 hole transport Effects 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 27
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000002484 cyclic voltammetry Methods 0.000 description 24
- 238000005259 measurement Methods 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000706 filtrate Substances 0.000 description 22
- 230000006870 function Effects 0.000 description 21
- 238000010521 absorption reaction Methods 0.000 description 20
- 238000000295 emission spectrum Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000002131 composite material Substances 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- 229910045601 alloy Inorganic materials 0.000 description 17
- 239000000956 alloy Substances 0.000 description 17
- 239000010453 quartz Substances 0.000 description 17
- 238000006722 reduction reaction Methods 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 16
- 239000002184 metal Substances 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- 239000011159 matrix material Substances 0.000 description 14
- 238000007254 oxidation reaction Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 13
- 239000011777 magnesium Substances 0.000 description 13
- 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 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 150000001340 alkali metals Chemical class 0.000 description 12
- 239000012298 atmosphere Substances 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 229910052744 lithium Inorganic materials 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 230000005484 gravity Effects 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 10
- 150000001342 alkaline earth metals Chemical class 0.000 description 10
- 230000005284 excitation Effects 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 239000012046 mixed solvent Substances 0.000 description 10
- 229910052697 platinum Inorganic materials 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000007983 Tris buffer Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 9
- 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 9
- 238000000746 purification Methods 0.000 description 9
- 238000004544 sputter deposition Methods 0.000 description 9
- LGSREBBBRHKSTD-UHFFFAOYSA-N 2-[4-[4-[2-[4-[4-(1,3-benzoxazol-2-yl)phenyl]phenyl]-6-pyridin-2-ylpyridin-3-yl]phenyl]phenyl]-1,3-benzoxazole Chemical compound N1=CC=CC=C1C(N=C1C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2OC3=CC=CC=C3N=2)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2OC3=CC=CC=C3N=2)C=C1 LGSREBBBRHKSTD-UHFFFAOYSA-N 0.000 description 8
- KMGPVPWEIOYERO-UHFFFAOYSA-N 2-[4-[4-[2-[4-[4-(1,3-benzoxazol-2-yl)phenyl]phenyl]-6-pyridin-3-ylpyridin-3-yl]phenyl]phenyl]-1,3-benzoxazole Chemical compound N=1C2=CC=CC=C2OC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(C(=N1)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2OC3=CC=CC=C3N=2)=CC=C1C1=CC=CN=C1 KMGPVPWEIOYERO-UHFFFAOYSA-N 0.000 description 8
- HQWWWYHXGKWCMN-UHFFFAOYSA-N 2-[4-[4-[2-[4-[4-(1,3-benzoxazol-2-yl)phenyl]phenyl]-6-pyridin-4-ylpyridin-3-yl]phenyl]phenyl]-1,3-benzoxazole Chemical compound N=1C2=CC=CC=C2OC=1C(C=C1)=CC=C1C(C=C1)=CC=C1C(C(=N1)C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2OC3=CC=CC=C3N=2)=CC=C1C1=CC=NC=C1 HQWWWYHXGKWCMN-UHFFFAOYSA-N 0.000 description 8
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 229910052796 boron Inorganic materials 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 229950005499 carbon tetrachloride Drugs 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 239000012212 insulator Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- QEUCEBOLURRTTK-UHFFFAOYSA-N 2,3-bis(4-bromophenyl)-6-pyridin-4-ylpyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2C=CN=CC=2)N=C1C1=CC=C(Br)C=C1 QEUCEBOLURRTTK-UHFFFAOYSA-N 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- 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 7
- 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 7
- 239000004065 semiconductor Substances 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 230000002194 synthesizing effect Effects 0.000 description 7
- 229910001930 tungsten oxide Inorganic materials 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- BXCFTABNIGPXQY-UHFFFAOYSA-N 2,3-bis(4-bromophenyl)-6-pyridin-2-ylpyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2N=CC=CC=2)N=C1C1=CC=C(Br)C=C1 BXCFTABNIGPXQY-UHFFFAOYSA-N 0.000 description 6
- RJXRGGLHIMZODC-UHFFFAOYSA-N 2,3-bis(4-bromophenyl)-6-pyridin-3-ylpyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2C=NC=CC=2)N=C1C1=CC=C(Br)C=C1 RJXRGGLHIMZODC-UHFFFAOYSA-N 0.000 description 6
- ZHTUYEZLMKDHPU-UHFFFAOYSA-N 2-[5,6-bis(4-bromophenyl)pyridin-2-yl]pyrimidine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C=2N=CC=CN=2)N=C1C1=CC=C(Br)C=C1 ZHTUYEZLMKDHPU-UHFFFAOYSA-N 0.000 description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000006161 Suzuki-Miyaura coupling reaction Methods 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 6
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 6
- 235000002597 Solanum melongena Nutrition 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229940125898 compound 5 Drugs 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- 229910052761 rare earth metal Inorganic materials 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 229910052814 silicon oxide Inorganic materials 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
- UQVFZEYHQJJGPD-UHFFFAOYSA-N 9-[4-(10-phenylanthracen-9-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 UQVFZEYHQJJGPD-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- PTTJBNMNZAUITF-UHFFFAOYSA-N [4-(1,3-benzoxazol-2-yl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=NC2=CC=CC=C2O1 PTTJBNMNZAUITF-UHFFFAOYSA-N 0.000 description 4
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- 238000010893 electron trap Methods 0.000 description 1
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- HCIIFBHDBOCSAF-UHFFFAOYSA-N octaethylporphyrin Chemical compound N1C(C=C2C(=C(CC)C(C=C3C(=C(CC)C(=C4)N3)CC)=N2)CC)=C(CC)C(CC)=C1C=C1C(CC)=C(CC)C4=N1 HCIIFBHDBOCSAF-UHFFFAOYSA-N 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
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- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000005215 recombination Methods 0.000 description 1
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- 238000012827 research and development Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
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- 229910001936 tantalum oxide Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- JIIYLLUYRFRKMG-UHFFFAOYSA-N tetrathianaphthacene Chemical compound C1=CC=CC2=C3SSC(C4=CC=CC=C44)=C3C3=C4SSC3=C21 JIIYLLUYRFRKMG-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- C07D403/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
-
- 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
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/12—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof structurally associated with, e.g. formed in or on a common substrate with, one or more electric light sources, e.g. electroluminescent light sources, and electrically or optically coupled thereto
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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Abstract
【解決手段】一般式(G1)で表されるベンゾオキサゾール誘導体。
(式中、Hetは、ピリジル基、または、ピリミジニル基を表し、Ar1〜Ar4は、それぞれ独立に、置換または無置換の炭素数6〜13のアリーレン基を表し、R11〜R18は、それぞれ独立に、水素、炭素数1〜4のアルキル基、炭素数1〜4のハロアルキル基、置換または無置換の炭素数6〜13のアリール基、ハロゲンのいずれかを表す。)該ベンゾオキサゾール誘導体は電子注入性を有するため、発光素子、発光装置および電子機器に好適に用いることができる。
【選択図】なし
Description
本実施の形態では、本発明のベンゾオキサゾール誘導体について説明する。本発明のベンゾオキサゾール誘導体は、ヘテロ環とベンゾオキサゾール骨格を有する。
本実施の形態では、実施の形態1で示したベンゾオキサゾール誘導体を用いた発光素子の一態様について、図1および図2を用いて説明する。
本実施の形態では、本発明に係る発光素子の一態様として、実施の形態1で示したベンゾオキサゾール誘導体を発光層に用いた構成について説明する。
本実施の形態では、本発明に係る発光素子の一態様として、実施の形態1で示したベンゾオキサゾール誘導体を電子注入層に用いた構成について説明する。
本実施の形態は、本発明に係る複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)の一態様について、図3を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する積層型発光素子である。各発光ユニットの構成としては、実施の形態2〜実施の形態4で示した構成と同様な構成を用いることができる。つまり、実施の形態2で示した発光素子は、1つの発光ユニットを有する発光素子である。本実施の形態では、複数の発光ユニットを有する発光素子について説明する。
本実施の形態では、本発明の発光素子を有する発光装置の一態様について説明する。
本実施の形態では、実施の形態6に示す発光装置をその一部に含む本発明の電子機器の態様について説明する。本発明の電子機器は、実施の形態2〜実施の形態5で示した発光素子を有し、低消費電力の表示部を有する。
(i)4−ブロモ−N−(2−ヒドロキシフェニル)ベンズアミドの合成
4−ブロモ−N−(2−ヒドロキシフェニル)ベンズアミドの合成スキームを(B−1)に示す。
2−(4−ブロモフェニル)ベンゾオキサゾールの合成スキームを(B−2)に示す。
4−(ベンゾオキサゾール−2−イル)フェニルボロン酸の合成スキームを(B−3)に示す。
(i)ピリジン−2−カルボキシアミドラゾンの合成
ピリジン−2−カルボキシアミドラゾンの合成スキームを(B−4)に示す。
5,6−ビス(4−ブロモフェニル)−3−(2−ピリジル)−1,2,4−トリアジンの合成スキームを(B−5)に示す。
5,6−ビス(4−ブロモフェニル)−2,2’−ビピリジンの合成スキームを(B−6)に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=7.10(d、J=8.4Hz、2H)、7.31−7.47(m、7H)、7.80−7.86(m、2H)、8.46(d、J=8.4Hz、1H)、8.54(d、J=7.8Hz、1H)、8.71(d、J=4.8Hz、1H)。
BOxP2BPyの合成スキームを(B−7)に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=7.33−7.43(m、7H)、7.58−7.69(m、8H)、7.77−7.89(m、7H)、7.95(d、J=8.4Hz、1H)、8.30−8.35(m、4H)、8.51(d、J=7.8Hz、1H)、8.64(d、J=7.8Hz、1H)、8.73(d、J=3.9Hz、1H)。
(i)ピリジン−3−カルボキシアミドラゾンの合成
ピリジン−3−カルボキシアミドラゾンの合成スキームを(C−1)に示す。
5,6−ビス(4−ブロモフェニル)−3−(3−ピリジル)−1,2,4−トリアジンの合成スキームを(C−2)に示す。
5,6−ビス(4−ブロモフェニル)−2,3’−ビピリジンの合成スキームを(C−3)に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=7.10(d、J=8.1Hz、2H)、7.31−7.48(m、7H)、7.81(d、J=1.8Hz、2H)、8.45(d、J=7.8Hz、1H)、8.68(dd、J=5.1、2.1Hz、1H)、9.31(d、J=2.1Hz、1H)。
BOxP2BPy(3)の合成スキームを(C−4)に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=7.35−7.45(m、7H)、7.59−7.69(m、8H)、7.78−7.92(m、8H)、8.31−8.36(m、4H)、8.52(d、J=8.4Hz、1H)、8.70(dd、J=4.8、1.5Hz、1H)、9.37(d、J=2.4Hz、1H)。
(i)ピリジン−4−カルボキシアミドラゾンの合成
ピリジン−4−カルボキシアミドラゾンの合成スキームを(D−1)に示す。
5,6−ビス(4−ブロモフェニル)−3−(4−ピリジル)−1,2,4−トリアジンの合成スキームを(D−2)に示す。
5,6−ビス(4−ブロモフェニル)−2,4’−ビピリジンの合成スキームを(D−3)に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=7.09(d、J=8.7Hz、2H)、7.33(d、J=8.4Hz、2H)、7.43−7.48(m、4H)、7.80−7.88(m、2H)、8.01(d、J=6.3Hz、2H)、8.75(d、J=5.7Hz、2H)。
13C NMR(75MHz、CDCl3):δ(ppm)=119.21、120.97、122.14、122.85、130.97、131.30、131.64、131.87、134.91、138.01、138.43、139.60、145.63、150.48、153.29、155.86。
BOxP2BPy(4)の合成スキームを(D−4)に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=7.35−7.43(m、6H)、7.59−7.69(m、8H)、7.77−7.82(m、6H)、7.93(d、J=4.5Hz、2H)、8.08(d、J=4.2Hz、2H)、8.31−8.35(m、4H)、8.78(d、J=4.2Hz、2H)。
(i)ピリミジン−2−カルボキシアミドラゾンの合成
ピリミジン−2−カルボキシアミドラゾンの合成スキームを(E−1)に示す。
5,6−ビス(4−ブロモフェニル)−3−(ピリミジン−2−イル)―1,2,4−トリアジンの合成スキームを(E−2)に示す。
2−〔5,6−ビス(4―ブロモフェニル)−2−ピリジル〕ピリミジンの合成スキームを(E−3)に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=7.10(d、J=8.4Hz、2H)、7.27−7.47(m、7H)、7.87(d、J=8.1Hz、1H)、8.53(d、J=7.8Hz、1H)、8.95(d、J=4.5Hz、2H)。
BOxP2PyPmの合成スキームを(E−4)に示す。
1H NMR(300MHz、CDCl3):δ(ppm)=7.33−7.43(m、7H)、7.57−7.68(m、8H)、7.76−7.81(m、6H)、8.00(d、J=7.8Hz、1H)、8.29−8.35(m、4H)、8.57(d、J=7.8Hz、1H)、8.98(d、J=5.1Hz、2H)。
まず、ガラス基板2101上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極2102を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
発光素子1と同一基板を用い、BOxP2BPyの代わりに、構造式(104)で表される2,2’−[2−(ビピリジン−2−イル)ピリジン−5,6−ジイルビス(ビフェニル−4,4’−ジイル)]ビスベンゾオキサゾール(略称:BOxP2PyPm)を用いて、発光素子1と同様に発光素子2を作製した。つまり、構造式(104)で表される2,2’−[2−(ビピリジン−2−イル)ピリジン−5,6−ジイルビス(ビフェニル−4,4’−ジイル)]ビスベンゾオキサゾール(略称:BOxP2PyPm)を30nmの膜厚となるように成膜し、電子輸送層2114を形成した。電子輸送層2114以外は発光素子1と同様に作製した。
発光素子1と同一基板を用い、BOxP2BPyの代わりに、構造式(103)で表される2,2’−[2,4’−ビピリジン−5,6−ジイルビス(ビフェニル−4,4’−ジイル)]ビスベンゾオキサゾール(略称:BOxP2BPy(4))を用いて、発光素子1と同様に発光素子3を作製した。つまり、構造式(103)で表される2,2’−[2,4’−ビピリジン−5,6−ジイルビス(ビフェニル−4,4’−ジイル)]ビスベンゾオキサゾール(略称:BOxP2BPy(4))を30nmの膜厚となるように成膜し、電子輸送層2114を形成した。電子輸送層2114以外は発光素子1と同様に作製した。
発光素子1と同一基板を用い、BOxP2BPyの代わりに、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を用いて、発光素子1と同様に比較発光素子4を作製した。つまり、トリス(8−キノリノラト)アルミニウム(III)(略称:Alq)を30nmの膜厚となるように成膜し、電子輸送層2114を形成した。電子輸送層2114以外は発光素子1と同様に作製した。
まず、ガラス基板2201上に、酸化珪素を含むインジウム錫酸化物(ITSO)をスパッタリング法にて成膜し、第1の電極2202を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
発光素子5と同一基板を用い、BOxP2BPyの代わりに、構造式(104)で表される2,2’−[2−(ビピリジン−2−イル)ピリジン−5,6−ジイルビス(ビフェニル−4,4’−ジイル)]ビスベンゾオキサゾール(略称:BOxP2PyPm)を用いて、発光素子5と同様に発光素子6を作製した。つまり、構造式(104)で表される2,2’−[2−(ビピリジン−2−イル)ピリジン−5,6−ジイルビス(ビフェニル−4,4’−ジイル)]ビスベンゾオキサゾール(略称:BOxP2PyPm)を20nmの膜厚となるように成膜し、電子輸送層(B)2215を形成した。電子輸送層(B)2215以外は発光素子5と同様に作製した。
発光素子5と同一基板を用い、BOxP2BPyの代わりに、構造式(103)で表される2,2’−[2,4’−ビピリジン−5,6−ジイルビス(ビフェニル−4,4’−ジイル)]ビスベンゾオキサゾール(略称:BOxP2BPy(4))を用いて、発光素子5と同様に発光素子7を作製した。つまり、構造式(103)で表される2,2’−[2,4’−ビピリジン−5,6−ジイルビス(ビフェニル−4,4’−ジイル)]ビスベンゾオキサゾール(略称:BOxP2BPy(4))を20nmの膜厚となるように成膜し、電子輸送層(B)2215を形成した。電子輸送層(B)2215以外は発光素子5と同様に作製した。
102 第1の電極
103 EL層
104 第2の電極
111 正孔注入層
112 正孔輸送層
113 発光層
114 電子輸送層
115 電子注入層
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 ソース側駆動回路
602 画素部
603 ゲート側駆動回路
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 EL層
617 第2の電極
618 発光素子
623 Nチャネル型TFT
624 Pチャネル型TFT
701 本体
702 表示部
703 操作スイッチ
704 操作スイッチ
710 本体
711 表示部
712 メモリ部
713 操作部
714 イヤホン
901 筐体
902 液晶層
903 バックライト
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 EL層
956 電極
1001 筐体
1002 筐体
1101 表示部
1102 スピーカー
1103 マイクロフォン
1104 操作キー
1105 ポインティングデバイス
1106 カメラ用レンズ
1107 外部接続端子
1108 イヤホン端子
1201 キーボード
1202 外部メモリスロット
1203 カメラ用レンズ
1204 ライト
2001 筐体
2002 光源
2101 ガラス基板
2102 第1の電極
2104 第2の電極
2111 複合材料を含む層
2112 正孔輸送層
2113 発光層
2114 電子輸送層
2115 電子注入層
2201 ガラス基板
2202 第1の電極
2204 第2の電極
2211 複合材料を含む層
2212 正孔輸送層
2213 発光層
2214 電子輸送層(A)
2215 電子輸送層(B)
2216 電子注入層
3001 照明装置
3002 テレビ装置
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9301 本体
9302 表示部
9303 筐体
9304 外部接続ポート
9305 リモコン受信部
9306 受像部
9307 バッテリー
9308 音声入力部
9309 操作キー
9310 接眼部
9401 本体
9402 筐体
9403 表示部
9404 音声入力部
9405 音声出力部
9406 操作キー
9407 外部接続ポート
9408 アンテナ
Claims (11)
- 一般式(G1)で表されるベンゾオキサゾール誘導体。
(式中、Hetは、ピリジル基、または、ピリミジニル基を表し、Ar1〜Ar4は、それぞれ独立に、置換または無置換の炭素数6〜13のアリーレン基を表し、R11〜R18は、それぞれ独立に、水素、炭素数1〜4のアルキル基、炭素数1〜4のハロアルキル基、置換または無置換の炭素数6〜13のアリール基、ハロゲンのいずれかを表す。) - 請求項1において、
Hetは一般式(G1−1)で表される置換基であるベンゾオキサゾール誘導体。
(式中、A1〜A3のうち、1つまたは2つは窒素を表し、残りは炭素を表す。) - 一般式(G2)で表されるベンゾオキサゾール誘導体。
(式中、A1〜A3のうち、1つまたは2つは窒素を表し、残りは炭素を表し、R11〜R18は、それぞれ独立に、水素、炭素数1〜4のアルキル基、炭素数1〜4のハロアルキル基、置換または無置換の炭素数6〜13のアリール基、ハロゲンのいずれかを表す。) - 一般式(G3)で表されるベンゾオキサゾール誘導体。
(式中、A1〜A3のうち、1つまたは2つは窒素を表し、残りは炭素を表し、R11〜R18は、それぞれ独立に、水素、炭素数1〜4のアルキル基、炭素数1〜4のハロアルキル基、置換または無置換の炭素数6〜13のアリール基、ハロゲンのいずれかを表す。) - 請求項1または請求項2において、
Ar1およびAr3は同一の構造であり、Ar2およびAr4は同一の構造であるベンゾオキサゾール誘導体。 - 請求項1乃至請求項5のいずれか一項において、
R11およびR15は同一の構造であり、R12およびR16は同一の構造であり、R13およびR17は同一の構造であり、R14およびR18は同一の構造であるベンゾオキサゾール誘導体。 - 一対の電極間に、
請求項1乃至請求項6のいずれか一項に記載のベンゾオキサゾール誘導体を有することを特徴とする発光素子。 - 陽極と陰極との間に発光層を有し、
前記陰極と前記発光層との間に、請求項1乃至請求項6のいずれか一項に記載のベンゾオキサゾール誘導体を有することを特徴とする発光素子。 - 請求項7または請求項8に記載の発光素子と、前記発光素子の発光を制御する制御回路を有する発光装置。
- 表示部を有し、
前記表示部は、請求項7または請求項8に記載の発光素子と前記発光素子の発光を制御する制御回路とを備えたことを特徴とする電子機器。 - 一般式(G11)で表される有機化合物。
(式中、Hetは、ピリジル基、または、ピリミジニル基を表し、Ar1およびAr3は、それぞれ独立に、置換または無置換の炭素数6〜13のアリーレン基を表し、X5およびX6は、それぞれ独立に、ハロゲンまたはトリフラート基を表す。)
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US9105852B2 (en) | 2012-02-17 | 2015-08-11 | Semiconductor Energy Laboratory Co., Ltd. | Bipyridine compound, light-emitting element material, organic semiconductor material, light-emitting element, display module, lighting module, light-emitting device, lighting device, display device and electronic device |
JP2019518324A (ja) * | 2016-04-08 | 2019-06-27 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電界発光化合物及びそれを含む有機電界発光デバイス |
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KR101647134B1 (ko) | 2010-03-29 | 2016-08-10 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
TWI591059B (zh) | 2011-08-25 | 2017-07-11 | 半導體能源研究所股份有限公司 | 發光元件,發光裝置,電子裝置,照明裝置以及新穎有機化合物 |
JP6007126B2 (ja) | 2012-02-29 | 2016-10-12 | 株式会社半導体エネルギー研究所 | フルオレン化合物、発光素子、発光装置、電子機器、および照明装置 |
JP6312960B2 (ja) | 2012-08-03 | 2018-04-18 | 株式会社半導体エネルギー研究所 | 発光素子、発光装置、電子機器、照明装置及び複素環化合物 |
TWI633100B (zh) | 2013-07-19 | 2018-08-21 | 半導體能源研究所股份有限公司 | 有機化合物、發光元件、顯示器模組、照明模組、發光裝置、顯示裝置、照明設備及電子裝置 |
JP2015125808A (ja) * | 2013-12-25 | 2015-07-06 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | 表示装置 |
KR102457008B1 (ko) | 2014-05-23 | 2022-10-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 헤테로고리 화합물, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치 |
CN110229145B (zh) * | 2019-03-28 | 2021-03-26 | 江苏三月科技股份有限公司 | 一种基于氮杂苯的有机化合物及其在oled上的应用 |
CN110283137A (zh) * | 2019-06-13 | 2019-09-27 | 爱斯特(成都)生物制药股份有限公司 | 一种2-(4-溴苯基)-1,3-苯并恶唑的制备方法 |
CN111393384B (zh) * | 2020-04-07 | 2023-08-29 | 上海应用技术大学 | 一种含邻位碳硼烷席夫碱配体的亚铜配合物的应用 |
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JP2001097950A (ja) * | 1999-10-01 | 2001-04-10 | Sankio Chemical Co Ltd | 新規なピリジン誘導体 |
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Publication number | Priority date | Publication date | Assignee | Title |
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US9105852B2 (en) | 2012-02-17 | 2015-08-11 | Semiconductor Energy Laboratory Co., Ltd. | Bipyridine compound, light-emitting element material, organic semiconductor material, light-emitting element, display module, lighting module, light-emitting device, lighting device, display device and electronic device |
JP2019518324A (ja) * | 2016-04-08 | 2019-06-27 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | 有機電界発光化合物及びそれを含む有機電界発光デバイス |
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US20120178933A1 (en) | 2012-07-12 |
TWI490215B (zh) | 2015-07-01 |
US20090284142A1 (en) | 2009-11-19 |
US8142911B2 (en) | 2012-03-27 |
CN101580504B (zh) | 2014-07-16 |
TW201008934A (en) | 2010-03-01 |
TWI452046B (zh) | 2014-09-11 |
US9209408B2 (en) | 2015-12-08 |
US20130261304A1 (en) | 2013-10-03 |
TW201437208A (zh) | 2014-10-01 |
CN101580504A (zh) | 2009-11-18 |
KR20090119717A (ko) | 2009-11-19 |
US8450485B2 (en) | 2013-05-28 |
KR101681999B1 (ko) | 2016-12-02 |
JP5491068B2 (ja) | 2014-05-14 |
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