JP2014500612A - 有機エレクトロルミネッセントデバイス用配合物 - Google Patents
有機エレクトロルミネッセントデバイス用配合物 Download PDFInfo
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- JP2014500612A JP2014500612A JP2013533104A JP2013533104A JP2014500612A JP 2014500612 A JP2014500612 A JP 2014500612A JP 2013533104 A JP2013533104 A JP 2013533104A JP 2013533104 A JP2013533104 A JP 2013533104A JP 2014500612 A JP2014500612 A JP 2014500612A
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- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 238000009472 formulation Methods 0.000 title claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 101
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- -1 carbazole compound Chemical class 0.000 claims abstract description 90
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 150000003254 radicals Chemical class 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- OWPJBAYCIXEHFA-UHFFFAOYSA-N 1-phenyl-3-(3-phenylphenyl)benzene Chemical compound C1=CC=CC=C1C1=CC=CC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 OWPJBAYCIXEHFA-UHFFFAOYSA-N 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 8
- 229910052805 deuterium Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- YAVCXSHORWKJQQ-UHFFFAOYSA-N 1-phenyl-2-(2-phenylphenyl)benzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 YAVCXSHORWKJQQ-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical compound C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- OFDVABAUFQJWEZ-UHFFFAOYSA-N 3-pyridin-3-ylpyridine Chemical group C1=CN=CC(C=2C=NC=CC=2)=C1 OFDVABAUFQJWEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 2
- 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 claims description 2
- 239000013522 chelant Substances 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 2
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 abstract description 9
- 150000002576 ketones Chemical class 0.000 abstract description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- 239000011159 matrix material Substances 0.000 description 14
- 238000002484 cyclic voltammetry Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 150000001716 carbazoles Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- 238000003775 Density Functional Theory Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 2
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 239000000956 alloy Substances 0.000 description 2
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- 229910052786 argon Inorganic materials 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000007429 general method Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
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- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
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- 238000001420 photoelectron spectroscopy Methods 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 125000005259 triarylamine group Chemical group 0.000 description 2
- 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 2
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
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- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
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- 150000003752 zinc compounds Chemical class 0.000 description 1
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Abstract
【選択図】 なし
Description
− 少なくとも1種のカルバゾール化合物、
− 少なくとも1種の電子輸送化合物、および
− 少なくとも1種の三重項エミッター化合物
を含む。
Arは、出現する毎に、5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系であり、これは、1以上のラジカルRにより置換されていてもよく;
R、R1は、出現する毎に、同一でも異なっていてもよく、H、D、F、Cl、Br、I、N(Ar1)2、CN、NO2、Si(R2)3、B(OR2)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、−CR2=CR2(Ar1)、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシ、もしくはチオアルコキシ基、または3〜40個のC原子を有する分枝もしくは環状アルキル、アルコキシ、もしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR2により置換されていてもよい)(ここで、1以上の隣接していないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S、またはCONR2により置きかえられていてもよく、1以上のH原子は、F、Cl、Br、I、CN、またはNO2により置きかえられていてもよい)、あるいは5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系(これらは、各場合において、1以上のラジカルR2により置換されていてもよい)、あるいは5〜60個の芳香族環原子を有するアリールオキシまたはヘテロアリールオキシ基(これらは、1以上のラジカルR2により置換されていてもよい)、あるいはこれらの系の組合せであり;ここで2以上の置換基R、R1、またはRとR1は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよく;
Ar1は、出現する毎に、同一でも異なっていてもよく、5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系であり、これらは、1以上のラジカルR2により置換されていてもよく;
R2は、出現する毎に、同一でも異なっていてもよく、H、または1〜20個のC原子を有する脂肪族、芳香族、および/もしくはヘテロ芳香族炭化水素ラジカル;または5〜60個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これらは、1以上のラジカルRにより置換されていてもよい)であり;ここで2以上の置換基R2は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよく;
nは、出現する毎に、同一でも異なっていてもよく、0、1、2、3、または4であり;
pは、出現する毎に、同一でも異なっていてもよく、0、1、2、3、または4であり;
qは、1、2、3、4、または5である。
Arは、出現する毎に、同一でも異なっていてもよく、5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系であり、これらは、各場合において、1以上の基R1により置換されていてもよく;
R1は、出現する毎に、同一でも異なっていてもよく、H、D、F、Cl、Br、I、CHO、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシ、もしくはチオアルコキシ基、または2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、または3〜40個のC原子を有する分枝もしくは環状アルキル、アルケニル、アルキニル、アルコキシ、もしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR2により置換されていてもよい)(ここで、1以上の隣接していないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S、またはCONR2により置きかえられていてもよく、1以上のH原子は、F、Cl、Br、I、CN、またはNO2により置きかえられていてもよい)、あるいは5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系(これらは、各場合において、1以上のラジカルR2により置換されていてもよい)、あるいは5〜60個の芳香族環原子を有するアリールオキシまたはヘテロアリールオキシ基(これらは、1以上のラジカルR2によって置換されていてもよい)、あるいはこれらの系の組合せであり;ここで2以上の隣接する置換基R1は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよく;
Ar1は、出現する毎に、同一でも異なっていてもよく、5〜40個の芳香族環原子を有する芳香族またはヘテロ芳香族環系であり、これらは、1以上のラジカルR2により置換されていてもよく;
R2は、出現する毎に、同一でも異なっていてもよく、H、D、CN、または1〜20個のC原子を有する脂肪族、芳香族、および/もしくはヘテロ芳香族炭化水素ラジカル(ここで、さらに、H原子は、Fにより置きかえられていてもよい)であり;ここで、2以上の置換基R2は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよい。
Zは、出現する毎に同一でも異なっていてもよく、CR1またはNであり;
nは、出現する毎に同一でも異なっていてもよく、0または1である。
Ar2は、出現する毎に同一でも異なっていてもよく、5〜60個の芳香族環原子を有する一価の芳香族またはヘテロ芳香族環系であり、これらは、各場合において、1以上のラジカルR1により置換されていてもよく;
Ar3は、5〜60個の芳香族環原子を有する二価の芳香族またはヘテロ芳香族環系であり、これらは、1以上のラジカルR1により置換されていてもよく;
R1は、式(2)のケトン化合物に関して上記に示した意味を有する。
Xは、出現する毎に同一でも異なっていてもよく、B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)、およびP(=O)R1から選択される二価のブリッジであり;
mは、出現する毎に、同一でも異なっていてもよく、0、1、2、または3であり;
oは、出現する毎に、同一でも異なっていてもよく、0、1、2、3、または4である。
DCyは、出現する毎に同一でも異なっていてもよく、少なくとも1種のドナー原子、好ましくは窒素、カルベンの形態での炭素、またはリンを含有する環状基であり、このドナー原子を介して環状基が金属に結合されており、この環状基は、さらには1以上の置換基R1を担持していてもよく;基DCyとCCyは、共有結合を介して互いに結合されており;
CCyは、出現する毎に同一でも異なっていてもよく、炭素原子を含有する環状基であり、この炭素原子を介して環状基が金属に結合されており、この環状基は、さらには1以上の置換基R1を担持していてもよく;
Aは、出現する毎に同一でも異なっていてもよく、モノアニオン性、二座キレート配位子、好ましくはジケトネート配位子である。
1.本発明による有機エレクトロルミネッセントデバイスは、非常に高い効率を有する。ここでの効率は、先行技術による、ホール輸送マトリックス材料と組み合わせた電子輸送マトリックス材料を使用する場合より良好である。
サイクリックボルタンメトリーおよび吸収スペクトルからのHOMO、LUMO、およびエネルギーギャップの決定
本願によれば、HOMOおよびLUMOの値、およびエネルギーギャップは、以下に記載される一般的な方法によって求められる。
測定技法:CV
初期パージ時間:300秒
クリーニング電位:−1V
クリーニング時間:10秒
析出電位:−0.2V
析出時間:10秒
開始電位:−0.2V
最終電位:1.6V
電圧ステップ:6mV
掃引速度:50mV/秒
その後、試料溶液1ml(ジクロロメタン1ml中の測定される物質10mg)を導電性塩溶液に添加し、混合物を5分間再び脱気する。その後、5回のさらなる測定サイクルを実施し、このうちの最後の3回を記録して評価する。上述したのと同じパラメータを設定する。
測定技法:CV
初期パージ時間:60秒
クリーニング電位:−1V
クリーニング時間:10秒
析出電位:−0.2V
析出時間:10秒
開始電位:−0.2V
最終電位:1.6V
電圧ステップ:6mV
掃引速度:50mV/秒
評価のために、試料溶液およびフェロセン溶液が添加された溶液について、フォワードカーブから最初に酸化が最大となる電圧の平均をとり、リターンカーブから関連する還元が最大となる電圧の平均をとり(VpおよびVF)、ここで、使用される電圧は、各場合において、フェロセンに対する電圧である。調査される物質のHOMO値EHOMOは、EHOMO=−[e・(VP−VF)+4.8eV]によって与えられ、式中、eは、素電荷を表す。
例1〜45
PLEDの作製
エミッターE1、本発明によるケトンK−1〜K−12、本発明によるトリアジンT−1〜T−4、および本発明によるカルバゾールC−1〜C−6の構造を以下に表す。
Claims (11)
- カルバゾール化合物、電子輸送化合物、三重項エミッター化合物、および少なくとも1種の溶媒を含有する配合物であって、前記電子輸送化合物がケトン化合物またはトリアジン化合物を包含し、前記カルバゾール化合物は、N原子を介して互いに接続された少なくとも2個のカルバゾール基を含有する配合物。
- カルバゾール化合物が式(1)の化合物であることを特徴とする請求項1に記載の配合物。
Arは、出現する毎に、5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系であり、これは、1以上のラジカルRにより置換されていてもよく;
R、R1は、出現する毎に、同一でも異なっていてもよく、H、D、F、Cl、Br、I、N(Ar1)2、CN、NO2、Si(R2)3、B(OR2)2、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、−CR2=CR2(Ar1)、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシ、もしくはチオアルコキシ基、または3〜40個のC原子を有する分枝もしくは環状アルキル、アルコキシ、もしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR2により置換されていてもよい)(ここで、1つのCH2基又は2以上の隣接していないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S、またはCONR2により置きかえられていてもよく、1以上のH原子は、F、Cl、Br、I、CN、またはNO2により置きかえられていてもよい)、あるいは5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系(これらは、各場合において、1以上のラジカルR2により置換されていてもよい)、あるいは5〜60個の芳香族環原子を有するアリールオキシまたはヘテロアリールオキシ基(これらは、1以上のラジカルR2により置換されていてもよい)、あるいはこれらの系の組合せであり;ここで2以上の置換基R、R1、またはRとR1は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよく;
Ar1は、出現する毎に、同一でも異なっていてもよく、5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系であり、これらは、1以上のラジカルR2により置換されていてもよく;
R2は、出現する毎に、同一でも異なっていてもよく、H、または1〜20個のC原子を有する脂肪族、芳香族、および/もしくはヘテロ芳香族炭化水素ラジカル;または5〜60個の芳香族環原子を有する芳香族もしくはヘテロ芳香族環系(これらは、1以上のラジカルRにより置換されていてもよい)であり;ここで2以上の置換基R2は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよく;
nは、出現する毎に、同一でも異なっていてもよく、0、1、2、3、または4であり;
pは、出現する毎に、同一でも異なっていてもよく、0、1、2、3、または4であり;
qは、1、2、3、4、または5である。
添え字qが1に等しい場合、これは、Arが二価の基を表すことを意味する。添え字qが1より大きい場合、これは、合計3以上のカルバゾール基が芳香族環系Arに結合されていることを意味する。Arは、q=2については三価の基であり、q>2については対応して多価の基である。添え字qは、好ましくは、=1または2であり、特に好ましくはq=1である。 - ケトン化合物が式(2)の化合物であることを特徴とする請求項1に記載の配合物。
Arは、出現する毎に、同一でも異なっていてもよく、5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系であり、これらは、各場合において、1以上の基R1により置換されていてもよく;
R1は、出現する毎に、同一でも異なっていてもよく、H、D、F、Cl、Br、I、CHO、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシ、もしくはチオアルコキシ基、または2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、または3〜40個のC原子を有する分枝もしくは環状アルキル、アルケニル、アルキニル、アルコキシ、もしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR2により置換されていてもよい)(ここで、1つのCH2基又は2以上の隣接していないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S、またはCONR2により置きかえられていてもよく、1以上のH原子は、F、Cl、Br、I、CN、またはNO2により置きかえられていてもよい)、あるいは5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系(これらは、各場合において、1以上のラジカルR2により置換されていてもよい)、あるいは5〜60個の芳香族環原子を有するアリールオキシまたはヘテロアリールオキシ基(これらは、1以上のラジカルR2によって置換されていてもよい)、あるいはこれらの系の組合せであり;ここで2以上の隣接する置換基R1は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよく;
Ar1は、出現する毎に、同一でも異なっていてもよく、5〜40個の芳香族環原子を有する芳香族またはヘテロ芳香族環系であり、これらは、1以上のラジカルR2により置換されていてもよく;
R2は、出現する毎に、同一でも異なっていてもよく、H、D、CN、または1〜20個のC原子を有する脂肪族、芳香族、および/もしくはヘテロ芳香族炭化水素ラジカル(ここで、さらに、H原子は、Fにより置きかえられていてもよい)であり;ここで、2以上の置換基R2は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよい。 - ケトン化合物の基Arが、フェニル、2−、3−または4−トリル、3−または4−o−キシリル、2−または4−m−キシリル、2−p−キシリル、o−、m−、またはp−tert−ブチルフェニル、o−、m−、またはp−フルオロフェニル、ベンゾフェノン、1−、2−、または3−フェニルメタノン、2−、3−、または4−ビフェニル、2−、3−、または4−o−テルフェニル、2−、3−、または4−m−テルフェニル、2−、3−、または4−p−テルフェニル、2’−p−テルフェニル、2’−、4’−、または5’−m−テルフェニル、3’−または4’−o−テルフェニル、p−、m,p−、o,p−、m,m−、o,m−、またはo,o−クアテルフェニル、キンクエフェニル、セキシフェニル、1−、2−、3−、または4−フルオレニル、2−、3−、または4−スピロ−9,9’−ビフルオレニル、1−、2−、3−、または4−(9,10−ジヒドロ)フェナントレニル、1−または2−ナフチル、2−、3−、4−、5−、6−、7−、または8−キノリニル、1−、3−、4−、5−、6−、7−、または8−イソキノリニル、1−または2−(4−メチルナフチル)、1−または2−(4−フェニルナフチル)、1−、または2−(4−ナフチルナフチル)、1−、2−、または3−(4−ナフチルフェニル)、2−、3−、または4−ピリジル、2−、4−または5−ピリミジニル、2−または3−ピラジニル、3−または4−ピリダジニル、2−(1,3,5−トリアジン)イル−、2−、3−、または4−(フェニルピリジル)、3−、4−、5−、または6−(2,2’−ビピリジル)、2−、4−、5−、または6−(3,3’−ビピリジル)、2−または3−(4,4’−ビピリジル)、およびこれらのラジカルの1以上の組合せを表すことを特徴とする請求項3に記載の配合物。
- トリアジン化合物が式(7)又は(8)の化合物であることを特徴とする請求項1に記載の配合物。
Ar2は、出現する毎に同一でも異なっていてもよく、5〜60個の芳香族環原子を有する一価の芳香族またはヘテロ芳香族環系であり、これらは、各場合において、1以上のラジカルR1により置換されていてもよく;
Ar3は、5〜60個の芳香族環原子を有する二価の芳香族またはヘテロ芳香族環系であり、これらは、1以上のラジカルR1により置換されていてもよく;
R1は、出現する毎に、同一でも異なっていてもよく、H、D、F、Cl、Br、I、CHO、C(=O)Ar1、P(=O)(Ar1)2、S(=O)Ar1、S(=O)2Ar1、CR2=CR2Ar1、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、1〜40個のC原子を有する直鎖アルキル、アルコキシ、もしくはチオアルコキシ基、または2〜40個のC原子を有する直鎖アルケニルもしくはアルキニル基、または3〜40個のC原子を有する分枝もしくは環状アルキル、アルケニル、アルキニル、アルコキシ、もしくはチオアルコキシ基(これらのそれぞれは、1以上のラジカルR2により置換されていてもよい)(ここで、1つのCH2基又は2以上の隣接していないCH2基は、R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S、またはCONR2により置きかえられていてもよく、1以上のH原子は、F、Cl、Br、I、CN、またはNO2により置きかえられていてもよい)、あるいは5〜60個の芳香族環原子を有する芳香族またはヘテロ芳香族環系(これらは、各場合において、1以上のラジカルR2により置換されていてもよい)、あるいは5〜60個の芳香族環原子を有するアリールオキシまたはヘテロアリールオキシ基(これらは、1以上のラジカルR2によって置換されていてもよい)、あるいはこれらの系の組合せであり;ここで2以上の隣接する置換基R1は、互いに単環または多環状、脂肪族、芳香族、またはヘテロ芳香族環系を形成していてもよく;
Ar1及びR2は、請求項3に示される意味を表す。 - 三重項エミッター化合物が、式(23)〜(26)の化合物であることを特徴とする請求項1〜5のいずれか1項以上に記載の配合物。
DCyは、出現する毎に同一でも異なっていてもよく、少なくとも1種のドナー原子、好ましくは窒素、カルベンの形態での炭素、またはリンを含有する環状基であり、このドナー原子を介して環状基が金属に結合されており、この環状基は、さらには1以上の置換基R1を担持していてもよく;基DCyとCCyは、共有結合を介して互いに結合されており;
CCyは、出現する毎に同一でも異なっていてもよく、炭素原子を含有する環状基であり、この炭素原子を介して環状基が金属に結合されており、この環状基は、さらには1以上の置換基R1を担持していてもよく;
Aは、出現する毎に同一でも異なっていてもよく、モノアニオン性、二座キレート配位子、好ましくはジケトネート配位子である。 - 有機エレクトロルミネッセントデバイスの製造における請求項1〜6のいずれか1項以上に記載の配合物の使用。
- カソード、アノード及び少なくとも1つのエレクトロルミネッセント層を具備する有機エレクトロルミネッセントデバイスであって、前記エレクトロルミネッセント層が、カルバゾール化合物、電子輸送化合物、三重項エミッター化合物を含有する混合物を含み、前記電子輸送化合物が、ケトン化合物またはトリアジン化合物を包含し、前記カルバゾール化合物が、N原子を介して互いに接続された少なくとも2個のカルバゾール基を含有することを特徴とする有機エレクトロルミネッセントデバイス。
- エレクトロルミネッセント層が、請求項1〜6のいずれか1項に記載の配合物から得られたことを特徴とする請求項8に記載の有機エレクトロルミネッセントデバイス。
- デバイス中に電子注入層を含まないことを特徴とする請求項8又は9に記載の有機エレクトロルミネッセントデバイス。
- エレクトロルミネッセント層が溶液を塗布して形成されたことを特徴とする請求項8〜10のいずれか1項以上に記載の有機エレクトロルミネッセントデバイス。
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-
2010
- 2010-10-14 DE DE102010048497A patent/DE102010048497A1/de not_active Withdrawn
-
2011
- 2011-09-15 KR KR1020137012363A patent/KR20130122633A/ko active Search and Examination
- 2011-09-15 CN CN201710112367.6A patent/CN106905219A/zh active Pending
- 2011-09-15 US US13/879,155 patent/US20130200357A1/en not_active Abandoned
- 2011-09-15 KR KR1020187029277A patent/KR20180115800A/ko active Search and Examination
- 2011-09-15 EP EP11761008.9A patent/EP2627730B1/de active Active
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JP2017011275A (ja) * | 2010-10-14 | 2017-01-12 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセントデバイス用配合物 |
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JP2019501516A (ja) * | 2015-10-23 | 2019-01-17 | サムスン エスディアイ カンパニー, リミテッドSamsung Sdi Co., Ltd. | 有機光電子素子用組成物、有機光電子素子および表示装置 |
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CN106905219A (zh) | 2017-06-30 |
TWI623605B (zh) | 2018-05-11 |
DE102010048497A1 (de) | 2012-04-19 |
US20130200357A1 (en) | 2013-08-08 |
CN103168085A (zh) | 2013-06-19 |
JP2017011275A (ja) | 2017-01-12 |
KR20130122633A (ko) | 2013-11-07 |
TW201229198A (en) | 2012-07-16 |
EP2627730B1 (de) | 2020-05-06 |
EP2627730A1 (de) | 2013-08-21 |
JP5996543B2 (ja) | 2016-09-21 |
KR20180115800A (ko) | 2018-10-23 |
WO2012048779A1 (de) | 2012-04-19 |
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