JP2009298779A - 芳香族アミン化合物、および芳香族アミン化合物を用いた発光素子、発光装置、照明装置、及び電子機器 - Google Patents
芳香族アミン化合物、および芳香族アミン化合物を用いた発光素子、発光装置、照明装置、及び電子機器 Download PDFInfo
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- JP2009298779A JP2009298779A JP2009116772A JP2009116772A JP2009298779A JP 2009298779 A JP2009298779 A JP 2009298779A JP 2009116772 A JP2009116772 A JP 2009116772A JP 2009116772 A JP2009116772 A JP 2009116772A JP 2009298779 A JP2009298779 A JP 2009298779A
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- emitting element
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- aromatic amine
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- -1 Aromatic amine compound Chemical class 0.000 title claims abstract description 141
- 239000000463 material Substances 0.000 claims description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 238000005286 illumination Methods 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 189
- 239000000126 substance Substances 0.000 description 71
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 40
- 239000000758 substrate Substances 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 38
- 239000002131 composite material Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 28
- 150000002894 organic compounds Chemical class 0.000 description 26
- 239000010408 film Substances 0.000 description 25
- 230000005525 hole transport Effects 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 15
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- 229910000476 molybdenum oxide Inorganic materials 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
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- 229910010272 inorganic material Inorganic materials 0.000 description 13
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- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 230000006866 deterioration Effects 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000005284 excitation Effects 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 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
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- 238000003756 stirring Methods 0.000 description 7
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- UUOYDHJVGOATFJ-UHFFFAOYSA-N [4-(n-(4-phenylphenyl)anilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 UUOYDHJVGOATFJ-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 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
- 239000003054 catalyst Substances 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 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
- 230000006872 improvement Effects 0.000 description 6
- 229910003437 indium oxide Inorganic materials 0.000 description 6
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 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 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- HPRNFQUWRYTMIB-UHFFFAOYSA-N 9-[4-(4-iodophenyl)phenyl]carbazole Chemical compound C1=CC(I)=CC=C1C1=CC=C(N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 HPRNFQUWRYTMIB-UHFFFAOYSA-N 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
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- 229910052796 boron Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
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- 229940125782 compound 2 Drugs 0.000 description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- YGNUPJXMDOFFDO-UHFFFAOYSA-N n,4-diphenylaniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 YGNUPJXMDOFFDO-UHFFFAOYSA-N 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
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- 238000004544 sputter deposition Methods 0.000 description 5
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 5
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- 239000011787 zinc oxide Substances 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
- 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
- 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 4
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- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
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- 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 4
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- 229910001935 vanadium oxide Inorganic materials 0.000 description 4
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 3
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- 229940126062 Compound A Drugs 0.000 description 3
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- 238000003775 Density Functional Theory Methods 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- NSABRUJKERBGOU-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical compound [Ir+3].[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 NSABRUJKERBGOU-UHFFFAOYSA-N 0.000 description 3
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 3
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- IWZZBBJTIUYDPZ-DVACKJPTSA-N (z)-4-hydroxypent-3-en-2-one;iridium;2-phenylpyridine Chemical compound [Ir].C\C(O)=C\C(C)=O.[C-]1=CC=CC=C1C1=CC=CC=N1.[C-]1=CC=CC=C1C1=CC=CC=N1 IWZZBBJTIUYDPZ-DVACKJPTSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical group C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
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- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- 230000036962 time dependent Effects 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-UHFFFAOYSA-N 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 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
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
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Abstract
【解決手段】一般式(1)で表される芳香族アミン化合物および一般式(1)で表される芳香族アミン化合物を用いて形成された発光素子、発光装置、電子機器を提供する。一般式(1)で表される芳香族アミン化合物を発光素子、発光装置、電子機器に用いることにより、発光効率の高い発光素子、発光装置、電子機器を得ることができる。
【選択図】なし
Description
本実施の形態では、本発明の一態様である芳香族アミン化合物について説明する。
本実施の形態では、実施の形態1で示した芳香族アミン化合物を用いた発光素子の一態様について図2(A)を用いて以下に説明する。
本実施の形態では、実施の形態2で示した構成と異なる構成の発光素子について説明する。
本実施の形態では、実施の形態2〜実施の形態3で示した構成と異なる構成の発光素子について説明する。
本実施の形態では、実施の形態2〜実施の形態4で示した構成と異なる構成の発光素子について説明する。
本実施の形態は、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)の態様について、図4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発光素子である。発光ユニットとしては、実施の形態2で示した発光物質を含む層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り、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、実施の形態1で示した芳香族アミン化合物を用いて作製された発光装置について図5を用いて説明する。
本実施の形態では、実施の形態7に示す発光装置をその一部に含む電子機器について説明する。本実施の形態の電子機器は、実施の形態1に示した芳香族アミン化合物を含み、信頼性が高い表示部を有する。また、発光効率の高い表示部を有する。また、発光効率が高いため、消費電力を低減できるという効果もある。
9−(4’−ヨードビフェニル−4−イル)−9H−カルバゾールの合成
4−フェニルトリフェニルアミンの合成スキーム(C−2)を以下に示す。
4−ブロモ−4’−フェニルトリフェニルアミンの合成スキーム(C−3)を以下に示す。
4−[N−(ビフェニル−4−イル)−N−フェニルアミノ]フェニルボロン酸の合成スキーム(C−4)を以下に示す。
1H NMR(CDCl3,300MHz):δ=7.05−7.12(m,1H)、7.18−7.25(m,6H)、7.27−7.36(m,5H)、7.39−7.63(m,12H)、7.66(d,J=8.3Hz,2H)、7.70−7.80(m,4H)、7.87(d,J=7.8Hz,2H)、8.16(d,J=7.8Hz,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。
正孔輸送層2104として、NPBを10nmの膜厚となるように成膜した。正孔輸送層2104以外は、発光素子1と同様に形成した。
正孔輸送層2104として、YGA骨格を有する化合物であり、下記構造式(131)で表される4−(カルバゾール−9−イル)フェニル−4’−フェニルトリフェニルアミン(略称:YGA1BP)を10nmの膜厚となるように成膜した。正孔輸送層2104以外は、発光素子1と同様に形成した。
正孔輸送層2104として、YGA骨格を有する化合物であり、下記構造式(132)で表される4−[4−(9H−カルバゾール−9−イル)フェニル]4’−フェニルトリフェニルアミン(略称:YGBA1BP)を10nmの膜厚となるように成膜した。正孔輸送層2104以外は、発光素子1と同様に形成した。
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。
以下では、下記構造式(132)で表される4−[4−(9H−カルバゾール−9−イル)フェニル]4’−フェニルトリフェニルアミン(略称:YGBA1BP)の合成方法について説明する。
1H NMR(CDCl3,300MHz):δ(ppm)=7.08(t, J=7.2Hz, 1H), 7.20−7.62 (m, 25H), 7.78 (d, J=8.1Hz, 2H), 8.15 (d, J=7.8Hz, 2H)。
本実施例の発光素子3は、複合材料を含む層2103以外は、実施例1の発光素子1と同様に形成した。発光素子3は、第1の電極2102が形成された面が下方となるように、第1の電極2102が形成された基板を真空蒸着装置内に設けられた基板ホルダーに固定し、10−4Pa程度まで減圧した後、第1の電極2102上に、YGTA1BPと酸化モリブデン(VI)とを共蒸着することにより、有機化合物と無機化合物とを複合してなる複合材料を含む層2103を形成した。その膜厚は50nmとし、YGTA1BPと酸化モリブデン(VI)との比率は、重量比で4:1(=YGTA1BP:酸化モリブデン)となるように調節した。
102 第1の電極
103 第1の層
104 第2の層
105 第3の層
106 第4の層
107 第2の電極
302 第1の電極
303 第1の層
304 第2の層
305 第3の層
306 第4の層
307 第2の電極
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 発光物質を含む層
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
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
953 絶縁層
954 隔壁層
955 発光物質を含む層
956 電極
2001 筐体
2002 光源
2101 ガラス基板
2102 第1の電極
2103 複合材料を含む層
2104 正孔輸送層
2105 発光層
2106a 第1の電子輸送層
2106b 第2の電子輸送層
2107 電子注入層
2108 第2の電極
2201 ガラス基板
2202 第1の電極
2203 複合材料を含む層
2204a 第1の正孔輸送層
2204b 第2の正孔輸送層
2205 発光層
2206a 第1の電子輸送層
2206b 第2の電子輸送層
2207 電子注入層
2208 第2の電極
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
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
9501 本体
9502 表示部
9503 筐体
9504 外部接続ポート
9505 リモコン受信部
9506 受像部
9507 バッテリー
9508 音声入力部
9509 操作キー
9510 接眼部
Claims (14)
- 一般式(1)で表される芳香族アミン化合物。
(式中、R1及びR2は、それぞれ、水素原子、炭素数1〜4のアルキル基、又は炭素数6〜13のアリール基のいずれかを表す。また、R3〜R14は、それぞれ、水素原子、又は炭素数1〜4のアルキル基を表す。また、Ar1及びAr2は、それぞれ炭素数6〜13のアリール基を表す。炭素数6〜13のアリール基はさらに置換基を有していてもよく、前記置換基が互いに結合して環を形成してもよい。) - 一般式(2)で表される芳香族アミン化合物。
- 一般式(3)で表される芳香族アミン化合物。
- 一般式(4)で表される芳香族アミン化合物。
- 一対の電極間に、請求項1乃至請求項4のいずれか一項に記載の芳香族アミン化合物を有する発光素子。
- 一対の電極間に、
発光層と、
前記発光層に接し、且つ請求項1乃至請求項4のいずれか一項に記載の芳香族アミン化合物を含む層と、を有する発光素子。 - 一対の電極間に、
請求項1乃至請求項4のいずれか一項に記載の芳香族アミン化合物を含む発光層を有する発光素子。 - 請求項6または請求項7において、
前記発光層は、燐光を発光する燐光材料を含む発光素子。 - 請求項8において、
前記燐光材料は、緑色の発光をする発光素子。 - 請求項6または請求項7において、
前記発光層は、蛍光を発光する蛍光材料を含む発光素子。 - 請求項10において、
前記蛍光材料は、青色の発光をする発光素子。 - 請求項5乃至請求項11のいずれか一項に記載の発光素子を有する発光装置。
- 請求項12に記載の発光装置を用いた照明装置。
- 表示部を有し、
前記表示部は、請求項12に記載の発光装置を備える電子機器。
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JP2021090055A (ja) * | 2019-12-03 | 2021-06-10 | 北京夏禾科技有限公司 | 有機エレクトロルミネセント素子 |
JP7164892B2 (ja) | 2019-12-03 | 2022-11-02 | 北京夏禾科技有限公司 | 有機エレクトロルミネセント素子 |
US11950507B2 (en) | 2019-12-03 | 2024-04-02 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescence device |
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JP5631559B2 (ja) | 2014-11-26 |
US8318322B2 (en) | 2012-11-27 |
US20130076237A1 (en) | 2013-03-28 |
US20090284143A1 (en) | 2009-11-19 |
US8852758B2 (en) | 2014-10-07 |
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