JP4823730B2 - Luminescent layer compound and organic electroluminescent device - Google Patents
Luminescent layer compound and organic electroluminescent device Download PDFInfo
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- JP4823730B2 JP4823730B2 JP2006077013A JP2006077013A JP4823730B2 JP 4823730 B2 JP4823730 B2 JP 4823730B2 JP 2006077013 A JP2006077013 A JP 2006077013A JP 2006077013 A JP2006077013 A JP 2006077013A JP 4823730 B2 JP4823730 B2 JP 4823730B2
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- Prior art keywords
- light emitting
- emitting layer
- group
- compound
- general formula
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- 150000001875 compounds Chemical class 0.000 title claims description 41
- 239000000463 material Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000002019 doping agent Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000005401 electroluminescence Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 87
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000010409 thin film Substances 0.000 description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 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 7
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 229940126543 compound 14 Drugs 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- -1 carbazole compound Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical class C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 2
- SJOKONNBSXFPSN-UHFFFAOYSA-N 9-(3-bromo-5-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC(Br)=C1 SJOKONNBSXFPSN-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 0 CCC=C(CC)[n]1c(ccc(*)c2)c2c2cc(*)ccc12 Chemical compound CCC=C(CC)[n]1c(ccc(*)c2)c2c2cc(*)ccc12 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- FFQIKQFRBLLLIO-UHFFFAOYSA-N [3,5-bis(9h-carbazol-1-yl)phenyl]boronic acid Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C1=CC(C=2C=3NC4=CC=CC=C4C=3C=CC=2)=CC(B(O)O)=C1 FFQIKQFRBLLLIO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000000434 field desorption mass spectrometry Methods 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 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 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 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 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KHFWENBBJCLMOB-UHFFFAOYSA-N 1-(4-iodophenyl)-9h-carbazole Chemical compound C1=CC(I)=CC=C1C1=CC=CC2=C1NC1=CC=CC=C21 KHFWENBBJCLMOB-UHFFFAOYSA-N 0.000 description 1
- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical group NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RNALQOUBQZUREK-UHFFFAOYSA-N C(C12)=CC=CC1c1ccccc1C2(c(cc1)ccc1-c(nc1)ccc1-[n]1c2ccccc2c2c1cccc2)c(cc1)ccc1-c(cc1)ncc1-[n]1c(cccc2)c2c2ccccc12 Chemical compound C(C12)=CC=CC1c1ccccc1C2(c(cc1)ccc1-c(nc1)ccc1-[n]1c2ccccc2c2c1cccc2)c(cc1)ccc1-c(cc1)ncc1-[n]1c(cccc2)c2c2ccccc12 RNALQOUBQZUREK-UHFFFAOYSA-N 0.000 description 1
- QIMPYPIVCIPPQO-UHFFFAOYSA-N Cc(cc(C(c1c2)(c(cc(cc3)-c4nc(Cc(cc5)cc(c6ccccc66)c5[n]6-c(cc5)ccc5Oc5ccc(C6(c7cc(-c8ccccn8)ccc7-c(cc7)c6cc7-c6ccccn6)c(cc6)ccc6Oc(cc6)ccc6-[n]6c7ccccc7c7c6cccc7)cc5)ccc4)c3-c1ccc2-c1nc(C)ccc1)c(cc1C)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)cc1)c1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 Chemical compound Cc(cc(C(c1c2)(c(cc(cc3)-c4nc(Cc(cc5)cc(c6ccccc66)c5[n]6-c(cc5)ccc5Oc5ccc(C6(c7cc(-c8ccccn8)ccc7-c(cc7)c6cc7-c6ccccn6)c(cc6)ccc6Oc(cc6)ccc6-[n]6c7ccccc7c7c6cccc7)cc5)ccc4)c3-c1ccc2-c1nc(C)ccc1)c(cc1C)ccc1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2)cc1)c1-c(cc1)ccc1-[n]1c2ccccc2c2c1cccc2 QIMPYPIVCIPPQO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ZPXSBJSLTDIQDY-UHFFFAOYSA-N c(cc1)cc(C2(c(cc3)ccc3-c(cc3)ccc3-[n]3c(cccc4)c4c4c3cccc4)c(cc3)ccc3-c(cc3)ccc3-[n]3c(cccc4)c4c4ccccc34)c1-c1c2cccc1 Chemical compound c(cc1)cc(C2(c(cc3)ccc3-c(cc3)ccc3-[n]3c(cccc4)c4c4c3cccc4)c(cc3)ccc3-c(cc3)ccc3-[n]3c(cccc4)c4c4ccccc34)c1-c1c2cccc1 ZPXSBJSLTDIQDY-UHFFFAOYSA-N 0.000 description 1
- PKQSBJFPGYRVQJ-UHFFFAOYSA-N c(cc1)cc(C2(c(cc3)ccc3-c3cc(-[n]4c5ccccc5c5ccccc45)cc(-[n]4c5ccccc5c5c4cccc5)c3)c(cc3)ccc3-c3cc(-[n]4c(cccc5)c5c5ccccc45)cc(-[n]4c5ccccc5c5ccccc45)c3)c1-c1c2cccc1 Chemical compound c(cc1)cc(C2(c(cc3)ccc3-c3cc(-[n]4c5ccccc5c5ccccc45)cc(-[n]4c5ccccc5c5c4cccc5)c3)c(cc3)ccc3-c3cc(-[n]4c(cccc5)c5c5ccccc45)cc(-[n]4c5ccccc5c5ccccc45)c3)c1-c1c2cccc1 PKQSBJFPGYRVQJ-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical class [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 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 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
本発明は新規な発光層化合物及び有機電界発光素子(以下、有機EL素子という)に関するものであり、詳しくは、燐光発光ドーパントと特定の構造を有するホスト化合物を併用することにより、高輝度を示す有機EL素子に関するものである。 The present invention relates to a novel light emitting layer compound and an organic electroluminescent device (hereinafter referred to as an organic EL device), and in particular, exhibits high brightness by using a phosphorescent dopant and a host compound having a specific structure in combination. The present invention relates to an organic EL element.
一般に、有機EL素子は、その最も簡単な構造としては発光層及び該層を挟んだ一対の対向電極から構成されている。即ち、有機EL素子では、両電極間に電界が印加されると、陰極から電子が注入され、陽極から正孔が注入され、これらが発光層において再結合エネルギー準位が伝導帯から価電子帯に戻る際にエネルギーとして光を放出する現象を利用する。 In general, the organic EL element has a light emitting layer and a pair of counter electrodes sandwiching the layer as its simplest structure. That is, in an organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode and holes are injected from the anode. These recombination energy levels in the light emitting layer change from the conduction band to the valence band. Utilizing the phenomenon of emitting light as energy when returning to.
近年、有機薄膜を用いたEL素子の開発が行われるようになった。特に発光効率を高めるため、電極からキャリアー注入の効率向上を目的として電極の種類の最適化を行い、芳香族ジアミンからなる正孔輸送層と8−ヒドロキシキノリンアルミニウム錯体(以下、Alq3という)からなる発光層とを電極間に薄膜として設けた素子の開発により、従来のアントラセン等の単結晶を用いた素子と比較して大幅な発光効率の改善がなされたことから、自発光・高速応答性といったと特徴を持つ高性能フラットパネルへの実用を目指して進められてきた。 In recent years, EL devices using organic thin films have been developed. In particular, in order to improve luminous efficiency, the type of electrode is optimized for the purpose of improving the efficiency of carrier injection from the electrode, and consists of a hole transport layer made of aromatic diamine and 8-hydroxyquinoline aluminum complex (hereinafter referred to as Alq3). The development of a device with a light emitting layer as a thin film between the electrodes has greatly improved the light emission efficiency compared to conventional devices using single crystals such as anthracene. It has been promoted with the aim of putting it into practical use for high performance flat panels.
また、素子の発光効率を上げる試みとして、蛍光ではなく燐光を用いることも検討されている。上記の芳香族ジアミンからなる正孔輸送層とAlq3からなる発光層とを設けた素子をはじめとした多くの素子が蛍光発光を利用したものであったが、燐光発光を用いる、すなわち、三重項励起状態からの発光を利用すれば、従来の蛍光(一重項)を用いた素子と比べて、3倍程度の効率向上が期待される。この目的のためにクマリン誘導体やベンゾフェノン誘導体を発光層とすることが検討されてきたが、極めて低い輝度しか得られなかった。その後、三重項状態を利用する試みとして、ユーロピウム錯体を用いることが検討されてきたが、これも高効率の発光には至らなかった。この燐光発光を利用した研究は、燐光発光ドーパントとしては、特許文献1に挙げられるようなイリジウム錯体等の有機金属錯体を中心に研究が多数行われている。
In addition, as an attempt to increase the light emission efficiency of the device, the use of phosphorescence instead of fluorescence has been studied. Many devices, including those provided with the hole transport layer composed of the above aromatic diamine and the light emitting layer composed of Alq3, used fluorescence emission, but use phosphorescence emission, that is, triplet. If light emission from an excited state is used, an efficiency improvement of about three times is expected compared to a conventional device using fluorescence (singlet). For this purpose, it has been studied to use a coumarin derivative or a benzophenone derivative as a light emitting layer, but only an extremely low luminance was obtained. Thereafter, the use of a europium complex has been studied as an attempt to utilize the triplet state, but this also did not lead to highly efficient light emission. Many studies using phosphorescence have been conducted mainly on organometallic complexes such as iridium complexes as described in
一方、実用性のある発光層とするためには、ドーパント材料とホスト材料の組み合わせが重要であり、このようなホスト材料として提案されているのは、特許文献2で紹介されているカルバゾール化合物のCBPが挙げられる。緑色燐光発光材料のトリス(2-フェニルピリジン)イリジウム錯体(以下、Ir(ppy)3という)のホスト材としてCBPを用いると、CBPは正孔を流し易く電子を流しにくい特性上、電荷注入バランスが崩れ、過剰の正孔は電子輸送側に流出し、結果としてIr(ppy)3からの発光効率が低下する。
On the other hand, a combination of a dopant material and a host material is important in order to obtain a practical light-emitting layer, and such a host material proposed is the carbazole compound introduced in
また、特許文献3で開示されている3-フェニル-4-(1'-ナフチル)-5-フェニル-1,2,4-トリアゾール(以下、TAZという)も燐光有機EL素子のホスト材として提案されているが、電子を流しやすく正孔を流しにくい特性上、発光領域が正孔輸送層側となる。したがって、正孔輸送層の材料によってはIr(ppy)3との相性問題により、Ir(ppy)3からの発光効率が低下することも考えられる。例えば、正孔輸送層として高性能、高信頼性、高寿命の点から最も良く使用されている4,4'-ビス(N-(1-ナフチル)-N-フェニルアミノ)ビフェニル(以下、NPBという)は、Ir(ppy)3との相性が悪く、Ir(ppy)3からNPBにエネルギー遷移が起き、発光効率が低下するという問題がある。
Further, 3-phenyl-4- (1′-naphthyl) -5-phenyl-1,2,4-triazole (hereinafter referred to as TAZ) disclosed in
更に、特許文献4〜6でフルオレン化合物が数多く開示されているが、特許文献4と6ではビスフェニルフルオレン化合物のフェニル部位にカルバゾール基が直接結合した化合物を開示するのみであり、連結基を介してカルバゾール基が結合した化合物の有用性を開示するものではない。連結基を介してカルバゾール置換芳香族化合物を結合させることで、高い三重項エネルギーを有するホスト材料となる。また、特許文献5においてはカルバゾール基が直接又は連結基を介して、フルオレン化合物に2個置換する化合物を開示しているが、カルバゾール基が3個以上置換した化合物の有用性を示すものではない。3個以上のカルバゾール基を置換することにより、熱的安定性が向上し、高効率かつ高い駆動安定性が期待できる。
Furthermore,
有機EL素子をフラットパネル・ディスプレイ等の表示素子に応用するためには、素子の発光効率を改善すると同時に駆動時の安定性を十分に確保する必要がある。本発明は、上記現状に鑑み、高効率かつ高い駆動安定性を有した実用上有用な有機EL素子及びそれに適する化合物を提供することを目的とする。 In order to apply the organic EL element to a display element such as a flat panel display, it is necessary to improve the light emission efficiency of the element and at the same time to ensure sufficient stability during driving. An object of this invention is to provide the practically useful organic EL element which has high efficiency and high drive stability in view of the said present condition, and a compound suitable for it.
本発明者らは、鋭意検討した結果、特定構造のビスフェニルフルオレン化合物を有機EL素子の発光層化合物に使用することで、上記課題を解決することができることを見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventors have found that the above-mentioned problems can be solved by using a bisphenylfluorene compound having a specific structure as a light-emitting layer compound of an organic EL device, and the present invention has been completed. It was.
本発明は、下記一般式(1)で表される発光層化合物である。
また、本発明は、下記一般式(2)で表される発光層化合物である。
また、本発明は、下記一般式(3)で表される発光層化合物である。
また、本発明は、下記一般式(4)で表される発光層化合物である。
更に本発明は、基板上に積層された陽極と陰極の間に、発光層を有する有機電界発光素子であって、該発光層が、燐光発光性ドーパントと上記いずれかの発光層化合物をホスト材料として含有することを特徴とする有機電界発光素子である。 Furthermore, the present invention provides an organic electroluminescent device having a light emitting layer between an anode and a cathode laminated on a substrate, wherein the light emitting layer comprises a phosphorescent dopant and any one of the above light emitting layer compounds as a host material. It is an organic electroluminescent element characterized by containing as.
また本発明は、陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を有してなる上記有機電界発光素子である。更に本発明は、発光層と電子注入輸送層の間に正孔阻止層を有してなる上記有機電界発光素子である。 The present invention is also the above-described organic electroluminescent device comprising a hole injecting and transporting layer between the anode and the light emitting layer and an electron injecting and transporting layer between the cathode and the light emitting layer. Furthermore, the present invention is the above organic electroluminescent device comprising a hole blocking layer between the light emitting layer and the electron injecting and transporting layer.
本発明の発光層化合物は前記一般式(1)〜(4)で表わされる化合物のいずれかである。本発明の発光層化合物は、2以上組合わせて使用することもできる。
一般式(1)、(3)及び(4)で表わされる化合物は、ビスフェニルフルオレン化合物のフェニル部位に酸素原子、硫黄原子、カルボニル基等の二価の連結基を介して、カルバゾール置換芳香族化合物を結合させることで、分子骨格の共役性を低下させ、高い三重項エネルギーを有する高効率かつ高い駆動安定性を有した実用上有用な有機EL素子を提供することができる。また、一般式(2)及び(3)で表わされる化合物は、カルバゾール置換基を3個以上結合させることで、より高い安定性を達成できる。
The light emitting layer compound of the present invention is any one of the compounds represented by the general formulas (1) to (4). Two or more light emitting layer compounds of the present invention can be used in combination.
The compounds represented by the general formulas (1), (3) and (4) are carbazole-substituted aromatics via a divalent linking group such as an oxygen atom, a sulfur atom or a carbonyl group at the phenyl moiety of the bisphenylfluorene compound. By bonding a compound, it is possible to provide a practically useful organic EL device having a high triplet energy and high efficiency and high driving stability by reducing the conjugation property of the molecular skeleton. In addition, the compounds represented by the general formulas (2) and (3) can achieve higher stability by bonding three or more carbazole substituents.
一般式(1)〜(3)において、Ar1は好ましくは、次のような基である。
ベンゼン環、ビフェニル環、ターフェニル環、フラン環、チオフェン環、ピリジン環、ピラジン環、ピリダジン環、ピリミジン環、トリアジン環などから生ずる2価の芳香族炭化水素基又は芳香族複素環基であり、単環構造のみを有しており、カルバゾール環との共役系を広げない点で共通する。
In the general formulas (1) to (3), Ar 1 is preferably the following group.
A divalent aromatic hydrocarbon group or aromatic heterocyclic group generated from a benzene ring, biphenyl ring, terphenyl ring, furan ring, thiophene ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, etc. They have only a single ring structure and are common in that they do not expand the conjugated system with the carbazole ring.
一般式(1)及び(3)において、Xは好ましくは、次のような基である。
酸素原子、硫黄原子、カルボニル基、カルボニルオキシ基、N−フェニルアミド基又はスルホニル基であり、ビフェニルフルオレン化合物のフェニル基とカルバゾール置換芳香族との共役系を切ることができる構造を有する点で共通する。
In the general formulas (1) and (3), X is preferably the following group.
Common in that it is an oxygen atom, sulfur atom, carbonyl group, carbonyloxy group, N-phenylamide group or sulfonyl group, and has a structure capable of cutting the conjugated system of the phenyl group of the biphenylfluorene compound and the carbazole-substituted aromatic To do.
一般式(1)〜(4)において、Rは好ましくは、次のような基である。
メチル、エチル、n-プロピル、2-プロピル、n-ブチル、イソブチル、tert-ブチル等の炭素数1〜4のアルキル基、ベンゼン環、ビフェニル環、ターフェニル環、フラン環、チオフェン環、ピリジン環、ピラジン環、ピリダジン環、ピリミジン環、トリアジン環などから生ずる1価の基であり、電気的な酸化還元に強く、熱的安定性に優れている点で共通する。
In the general formulas (1) to (4), R is preferably the following group.
C1-C4 alkyl groups such as methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, tert-butyl, benzene ring, biphenyl ring, terphenyl ring, furan ring, thiophene ring, pyridine ring , A monovalent group formed from a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, etc., which are common in that they are resistant to electrical redox and have excellent thermal stability.
一般式(1)〜(4)において、複数のX、Ar1及びRがある場合、これらは同一であっても、異なってもよい。しかし、これらの化合物を合成する上では、対応する位置のX、Ar1及びRは同じ基であることが有利である。 In the general formulas (1) to (4), when there are a plurality of X, Ar 1 and R, these may be the same or different. However, in synthesizing these compounds, X, Ar 1 and R at corresponding positions are advantageously the same group.
一般式(1)で表される化合物の合成法の一つとしては、対応するフルオレン誘導体と対応するハロゲン化フェニルカルバゾールを、有機溶媒中又は無溶媒で、塩基及び触媒の存在下、窒素雰囲気下、100〜200℃程度の温度で、1〜90時間程度反応させて得ることができる。ハロゲン化フェニルカルバゾールのハロゲン原子としては、塩素、臭素、よう素等が挙げられる。使用される塩基としては、炭酸カリウム、炭酸ナトリウム、炭酸セシウム、リン酸カリウム、水酸化リチウム、水酸化ナトリウム、ナトリウム tert-ブトキシド、カリウム tert-ブトキシドのような無機塩基、ピリジン、ピコリン、トリエチルアミンのような有機塩基が挙げられる。触媒としては、銅粉、酸化銅、ハロゲン化銅、硫酸銅等の銅系触媒、又は酢酸パラジウム、ビス(ジベンジリデンアセトン)パラジウムなどのパラジウム源と、トリtert-ブチルホスフィンなどの配位子により形成されるパラジウム錯体系触媒が挙げられる。溶媒は、原料を溶解して、反応を行わせることができるものであればよい。例えば、トルエン、キシレン、ジオキサン、テトラリン、キノリン、ニトロベンゼン、ジメチルスルフォキシド、N、N-ジメチルホルムアミド等の溶媒が挙げられる。 As one method for synthesizing the compound represented by the general formula (1), the corresponding fluorene derivative and the corresponding halogenated phenylcarbazole are used in an organic solvent or without a solvent in the presence of a base and a catalyst in a nitrogen atmosphere. It can be obtained by reacting at a temperature of about 100 to 200 ° C. for about 1 to 90 hours. Examples of the halogen atom of the halogenated phenylcarbazole include chlorine, bromine and iodine. The bases used are inorganic bases such as potassium carbonate, sodium carbonate, cesium carbonate, potassium phosphate, lithium hydroxide, sodium hydroxide, sodium tert-butoxide, potassium tert-butoxide, pyridine, picoline, triethylamine and the like. Organic bases. Catalysts include copper powders, copper oxides, copper halides, copper sulfates and other copper catalysts, or palladium sources such as palladium acetate and bis (dibenzylideneacetone) palladium and ligands such as tri-tert-butylphosphine. The palladium complex catalyst formed is mentioned. The solvent should just be a thing which can melt | dissolve a raw material and can make it react. Examples thereof include solvents such as toluene, xylene, dioxane, tetralin, quinoline, nitrobenzene, dimethyl sulfoxide, N, N-dimethylformamide and the like.
反応終了後、水を加えて有機層を分離し、これを濃縮し、酢酸エチル等の低沸点溶媒で洗浄し、減圧乾燥することにより、本発明の化合物を得る。本発明の化合物を有機EL材料の発光層化合物、特にホスト材料としての性能を高めるためには、更に昇華精製することが好ましい。 After completion of the reaction, water is added to separate the organic layer, which is concentrated, washed with a low boiling point solvent such as ethyl acetate, and dried under reduced pressure to obtain the compound of the present invention. In order to enhance the performance of the compound of the present invention as a light emitting layer compound of an organic EL material, particularly as a host material, it is preferable to further sublimate and purify it.
次に、一般式(1)〜(4)で表される化合物の好ましい具体例を以下に示すが、これらに限定するものではない。なお、化学式の下に記載された番号は化合物番号である。 Next, although the preferable specific example of a compound represented by General formula (1)-(4) is shown below, it is not limited to these. In addition, the number described under the chemical formula is a compound number.
発光層における燐光発光ドーパント材料としては、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から選ばれる少なくとも一つの金属を含む有機金属錯体を含有するものがよい。かかる有機金属錯体は、前記特許文献等で公知であり、これらが選択されて使用可能である。 The phosphorescent dopant material in the light emitting layer preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold. Such organometallic complexes are known in the above-mentioned patent documents and the like, and these can be selected and used.
好ましい燐光発光ドーパントとしては、Ir等の貴金属元素を中心金属として有するIr(ppy)3等の錯体類、Ir(bt)2・acac3等の錯体類、PtOEt3等の錯体類が挙げられる。これらの錯体類の具体例を以下に示すが、下記の化合物に限定されない。 Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as Ir (bt) 2 · acac3, and complexes such as PtOEt3. Specific examples of these complexes are shown below, but are not limited to the following compounds.
前記燐光発光ドーパントが発光層中に含有される量は、5〜10重量%の範囲にあることが好ましい。 The amount of the phosphorescent dopant contained in the light emitting layer is preferably in the range of 5 to 10% by weight.
次に、本発明の発光層化合物を用いた、有機EL素子について説明する。 Next, an organic EL device using the light emitting layer compound of the present invention will be described.
本発明の有機EL素子は、基板上に積層された陽極と陰極の間に、少なくとも1つの発光層を有する有機EL素子であり、該発光層が燐光発光性ドーパントと、一般式(1)〜(4)で表わされる化合物を含有することを特徴とする。
そして、好ましい有機EL素子の構造としては、陽極と発光層の間に正孔注入輸送層及び陰極と発光層の間に電子注入輸送層を有した構造や発光層と電子注入輸送層の間に正孔阻止層を有してなる構造がある。
The organic EL device of the present invention is an organic EL device having at least one light-emitting layer between an anode and a cathode laminated on a substrate, and the light-emitting layer includes a phosphorescent dopant, and general formulas (1) to (1) to (1). It contains the compound represented by (4).
As a preferable structure of the organic EL element, a structure having a hole injecting and transporting layer between the anode and the light emitting layer and an electron injecting and transporting layer between the cathode and the light emitting layer, or between the light emitting layer and the electron injecting and transporting layer. There is a structure having a hole blocking layer.
次に、本発明の有機EL素子の構造について、図面を参照しながら説明するが、本発明の有機EL素子の構造は何ら図示のものに限定されるものではない。 Next, the structure of the organic EL element of the present invention will be described with reference to the drawings. However, the structure of the organic EL element of the present invention is not limited to the illustrated one.
図1は本発明に用いられる一般的な有機EL素子の構造例を模式的に示す断面図であり、1は基板、2は陽極、3は正孔注入層、4は正孔輸送層、5は発光層、6は電子輸送層、7は陰極を各々表わす。本発明の有機EL素子では、基板、陽極、発光層及び陰極を必須の層として有するが、必須の層以外の層以外に、正孔注入輸送層、電子注入輸送層を有することがよく、更に発光層と電子注入輸送層の間に正孔阻止層を有することがよい。なお、正孔注入輸送層は、正孔注入層と正孔輸送層のいずれか又は両者を意味し、電子注入輸送層は、電子注入層と電子輸送層のいずれか又は両者を意味する。 FIG. 1 is a cross-sectional view schematically showing a structural example of a general organic EL element used in the present invention, wherein 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, Represents a light emitting layer, 6 represents an electron transport layer, and 7 represents a cathode. The organic EL device of the present invention has a substrate, an anode, a light emitting layer, and a cathode as essential layers. In addition to the layers other than the essential layers, the organic EL device preferably has a hole injecting and transporting layer and an electron injecting and transporting layer. A hole blocking layer is preferably provided between the light emitting layer and the electron injecting and transporting layer. The hole injection / transport layer means either or both of a hole injection layer and a hole transport layer, and the electron injection / transport layer means either or both of an electron injection layer and an electron transport layer.
なお、図1とは逆の構造、すなわち、基板1上に陰極7、電子輸送層6、発光層5、正孔輸送層4、陽極2の順に積層することも可能であり、既述したように少なくとも一方が透明性の高い2枚の基板の間に本発明の有機EL素子を設けることも可能である。この場合も、必要により層を追加したり、省略したりすることが可能である。
In addition, it is also possible to laminate | stack the
本発明は、有機EL素子が、単一の素子、アレイ状に配置された構造からなる素子、陽極と陰極がX−Yマトリックス状に配置された構造のいずれにおいても適用することができる。本発明の有機EL素子によれば、発光層に特定の骨格を有する化合物と、燐光発光ドーパントを含有させることにより、従来の一重項状態からの発光を用いた素子よりも発光効率が高くかつ駆動安定性においても大きく改善された素子が得られ、フルカラーあるいはマルチカラーのパネルへの応用において優れた性能を発揮できる。 The present invention can be applied to any of an organic EL element having a single element, an element having a structure arranged in an array, and a structure having an anode and a cathode arranged in an XY matrix. According to the organic EL device of the present invention, the light emitting layer contains a compound having a specific skeleton and a phosphorescent light emitting dopant, so that the light emitting efficiency is higher than that of a conventional device using light emission from a singlet state and driving. A device with greatly improved stability can be obtained, and excellent performance can be exhibited in application to full-color or multi-color panels.
以下、本発明につき、実施例によって更に詳しく説明するが、本発明は勿論、これらの実施例に限定されるものではなく、その要旨を越えない限りにおいて、種々の形態で実施することが可能である。 Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is of course not limited to these examples, and can be implemented in various forms as long as the gist thereof is not exceeded. is there.
実施例1
化合物1の合成
脱気窒素置換した500ml三口フラスコに9-(ビス(p-ヒドロキシフェニル))フルオレン(BPFL) 5.43g(15.40 mmol)、p-ヨードフェニルカルバゾール 15.00g(40.43 mmol)、ヨウ化銅2.98g(15.65 mmol)、N,N‘−ジメチルグリシン塩酸塩 3.00g(21.49 mmol)、炭酸セシウム 16.40 g(50.33 mmol)、を加え、これに1,4-ジオキサン 300 mlを加えて攪拌させた。その後120℃まで加熱し、72時間攪拌した。室温まで冷却した後、反応溶液を濾過し、溶媒を減圧留去した。得られた茶色粉末19gを活性炭で処理した後、シリカゲルクロマトグラフィーで精製して白色固体14.36g(収率89.2%)を得た。
化合物1のFD−MS(M+)は832、融点は169℃であった。
Example 1
Synthesis of
実施例2
化合物14の合成
窒素雰囲気下、200ml三口フラスコに無水N,N'-ジメチルホルムアミド中で水素化ナトリウム(55%)17g(0.39 mol)をカルバゾール71 g(0.43 mol)に作用させた後、1-ブロモ-3,5-ジフルオロベンゼン25g(0.13 mol)を添加し、80℃で10時間、120℃で0.5時間、140℃で1時間攪拌した。得られた溶液に水1000ml、メタノール300mlを加えて、濾過した。得られた固体を水500mlを用いて3回、メタノール500mlを用いて3回洗浄した。その後、THFとメタノールにより晶析を行い、1-ブロモ-3,5-ビス(N-カルバゾリル)ベンゼン32g(収率58.3%)を得た。
Example 2
Synthesis of Compound 14 Under a nitrogen atmosphere, 17 g (0.39 mol) of sodium hydride (55%) was allowed to act on 71 g (0.43 mol) of carbazole in anhydrous N, N′-dimethylformamide in a 200 ml three-necked flask. Bromo-3,5-difluorobenzene (25 g, 0.13 mol) was added, and the mixture was stirred at 80 ° C. for 10 hours, 120 ° C. for 0.5 hour, and 140 ° C. for 1 hour. 1000 ml of water and 300 ml of methanol were added to the resulting solution and filtered. The obtained solid was washed 3 times with 500 ml of water and 3 times with 500 ml of methanol. Thereafter, crystallization was performed with THF and methanol to obtain 32 g (yield 58.3%) of 1-bromo-3,5-bis (N-carbazolyl) benzene.
窒素雰囲気下、1000ml三口フラスコに無水THF100ml、マグネシウム1.46g(60mmol)を仕込み、THF還流下、1-ブロモ-3,5-ビス(N-カルバゾリル)ベンゼン24.3g(50.0mmol)のTHF220ml溶液をゆっくりと滴下した。2時間後、室温まで冷却し、得られた溶液を、0℃下でトリメトキシボラン6.23g(60.0mmol)のTHF150ml溶液に滴下し、1時間攪拌した。その後、メタノールと塩酸を加え、12時間攪拌した。得られた溶液を濾別し、酢酸エチルと水を用いて洗浄した。有機層と水層に分け、硫酸マグネシウムで乾燥後、溶媒を減圧留去した。得られた固体をシリカゲルクロマトグラフィーで精製し、3,5−ビスカルバゾリルフェニルボロン酸を14.6g(収率64.5%)得た。 In a nitrogen atmosphere, charge 1000 ml of anhydrous THF and 1.46 g (60 mmol) of magnesium into a 1000 ml three-necked flask, and slowly add a solution of 24.3 g (50.0 mmol) of 1-bromo-3,5-bis (N-carbazolyl) benzene in 220 ml of THF under reflux of THF. And dripped. After 2 hours, the mixture was cooled to room temperature, and the resulting solution was added dropwise to a THF 150 ml solution of trimethoxyborane 6.23 g (60.0 mmol) at 0 ° C. and stirred for 1 hour. Then, methanol and hydrochloric acid were added and stirred for 12 hours. The resulting solution was filtered off and washed with ethyl acetate and water. The organic layer and the aqueous layer were separated and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained solid was purified by silica gel chromatography to obtain 14.6 g (yield 64.5%) of 3,5-biscarbazolylphenylboronic acid.
500ml三口フラスコに9-(ビス(p-ヨードフェニル))フルオレン 10.7g(15mmol)、3,5−ビスカルバゾリルフェニルボロン酸 13.9g(32.5mmol)、テトラキストリフェニルホスフィンパラジウム1.73g(1.5mmol)、2M−炭酸ナトリウム水溶液30mlを加え、これにトルエン150mlを加えて攪拌させた。その後90℃まで加熱し、3.5時間攪拌した。室温まで冷却した後、反応溶液を濾過し、溶媒を減圧留去した。得られた茶色粉末30.5gを活性炭で処理した後、シリカゲルクロマトグラフィーを行い、得られた固体をトルエン−ヘキサンを用いて晶析を行うことで白色固体9.9g(収率58.4%)を得た。
化合物14のFD−MS(M+)は1130、融点は381℃であった。
In a 500 ml three-necked flask, 10.7 g (15 mmol) of 9- (bis (p-iodophenyl)) fluorene, 13.9 g (32.5 mmol) of 3,5-biscarbazolylphenylboronic acid, 1.73 g (1.5 mmol) of tetrakistriphenylphosphine palladium ), 30 ml of 2M sodium carbonate aqueous solution was added, and 150 ml of toluene was added thereto and stirred. Thereafter, the mixture was heated to 90 ° C. and stirred for 3.5 hours. After cooling to room temperature, the reaction solution was filtered and the solvent was distilled off under reduced pressure. After treating 30.5 g of the obtained brown powder with activated carbon, silica gel chromatography was performed, and the obtained solid was crystallized using toluene-hexane to obtain a white solid 9.9 g (yield 58.4%). .
Compound 14 had an FD-MS (M +) of 1130 and a melting point of 381 ° C.
実施例3
ガラス基板上に真空蒸着法にて、真空度4.0×10-4 Pa の条件にて化合物1とIr(ppy)3とを異なる蒸着源から蒸着し、Ir(ppy)3の濃度が7.0 %であるような薄膜を1.0Å/秒にて50nmの厚さで形成した。
作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物1の極大吸収波長であり、そのときに出てくる光を観察した。結果を表1に示す。
Example 3
The prepared thin film was evaluated with a fluorescence measuring apparatus. The excitation wavelength is the maximum absorption wavelength of
実施例4
ホスト材料として化合物14を用いた以外は実施例3と同様にして薄膜を作成し、作成した薄膜を、蛍光測定装置にて評価した。励起波長は化合物14の極大吸収波長であり、そのときに出てくる光を観察した。結果を表1に示す。
Example 4
A thin film was prepared in the same manner as in Example 3 except that compound 14 was used as the host material, and the prepared thin film was evaluated with a fluorescence measuring apparatus. The excitation wavelength is the maximum absorption wavelength of Compound 14, and the light emitted at that time was observed. The results are shown in Table 1.
比較例1
薄膜主成分をAlq3に変えて薄膜を作成した以外は、実施例3と4と同様に行った。結果を表1に示す。
Comparative Example 1
The same procedure as in Examples 3 and 4 was performed, except that the thin film main component was changed to Alq3 to prepare a thin film. The results are shown in Table 1.
発光層の主たる材料に化合物1又は化合物14を用いた場合は、Ir(ppy)3にエネルギーが遷移し、Ir(ppy)3からの発光が観察されるが、Alq3を用いた場合は、Ir(ppy)3にエネルギーが遷移せず、Alq3自身が蛍光を発することがわかる。
When
実施例5
図1において、正孔注入層を省略し、電子注入層を追加した構成の有機EL素子を作成した。膜厚150nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-4 Paで積層させた。まず、ITO上に正孔輸送層としてNPBを60nmの厚さに形成した。
次に、正孔輸送層上に、発光層として化合物1とIr(ppy)3とを異なる蒸着源から、共蒸着し、25nmの厚さに形成した。この時、Ir(ppy)3の濃度は7.0 %であった。次に、電子輸送層としてAlq3を50nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170nmの厚さに形成し、有機EL素子を作成した。
Example 5
In FIG. 1, an organic EL element having a configuration in which the hole injection layer is omitted and an electron injection layer is added is prepared. Each thin film was laminated at a vacuum degree of 4.0 × 10 −4 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a thickness of 150 nm was formed. First, NPB was formed to a thickness of 60 nm on ITO as a hole transport layer.
Next,
実施例6
発光層として化合物14を用いた以外は実施例5と同様にして有機EL素子を作成した。
Example 6
An organic EL device was produced in the same manner as in Example 5 except that Compound 14 was used as the light emitting layer.
得られた有機EL素子に外部電源を接続し直流電圧を印加したところ、表2のような発光特性を有することが確認された。表2において、輝度、電圧及び発光効率は、10mA/cm2での値を示す。なお、素子発光スペクトルの極大波長は517 nmであり、Ir(ppy)3からの発光が得られていることがわかった。 When an external power source was connected to the obtained organic EL element and a DC voltage was applied, it was confirmed that the organic EL element had the light emission characteristics as shown in Table 2. In Table 2, the luminance, voltage, and luminous efficiency show values at 10 mA / cm 2 . The maximum wavelength of the device emission spectrum was 517 nm, indicating that light emission from Ir (ppy) 3 was obtained.
比較例2
正孔輸送層としてHMTPDを、発光層の主成分としてTAZを用いた以外は実施例5と同様にして有機EL素子を作成した。
Comparative Example 2
An organic EL device was prepared in the same manner as in Example 5 except that HMTPD was used as the hole transport layer and TAZ was used as the main component of the light emitting layer.
比較例3
発光層の主成分として、TAZを用いた以外は実施例5と同様にして有機EL素子を作成した。
Comparative Example 3
An organic EL device was produced in the same manner as in Example 5 except that TAZ was used as the main component of the light emitting layer.
比較例4
比較例3において、発光層のホスト材料としてTAZの代わりに、特許第3079909号公報に記載の下記化合物を用いた以外は実施例5と同様にして有機EL素子を作成した。
In Comparative Example 3, an organic EL device was produced in the same manner as in Example 5 except that the following compound described in Japanese Patent No. 3079909 was used instead of TAZ as the host material of the light emitting layer.
本発明の有機EL素子は、低電圧において高輝度・高効率で発光させることが可能となる。従って、本発明による有機EL素子はフラットパネル・ディスプレイ(例えばOAコンピュータ用や壁掛けテレビ)、車載表示素子、携帯電話表示や面発光体としての特徴を生かした光源(例えば、複写機の光源、液晶ディスプレイや計器類のバックライト光源)、表示板、標識灯への応用が考えられ、その技術的価値は大きいものである。 The organic EL device of the present invention can emit light with high luminance and high efficiency at a low voltage. Accordingly, the organic EL device according to the present invention is a flat panel display (for example, for OA computers or wall-mounted televisions), an in-vehicle display device, a light source utilizing characteristics of a mobile phone display or a surface light emitter (for example, a light source of a copying machine, a liquid crystal). It can be applied to backlight sources for displays and instruments, display panels, and indicator lights, and its technical value is great.
1 基板、2 陽極、3 正孔注入層、4 正孔輸送層、5 発光層、6 電子輸送層、7 陰極 1 substrate, 2 anode, 3 hole injection layer, 4 hole transport layer, 5 light emitting layer, 6 electron transport layer, 7 cathode
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