JPWO2009057567A1 - 発光素子材料および発光素子 - Google Patents
発光素子材料および発光素子 Download PDFInfo
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- JPWO2009057567A1 JPWO2009057567A1 JP2008555548A JP2008555548A JPWO2009057567A1 JP WO2009057567 A1 JPWO2009057567 A1 JP WO2009057567A1 JP 2008555548 A JP2008555548 A JP 2008555548A JP 2008555548 A JP2008555548 A JP 2008555548A JP WO2009057567 A1 JPWO2009057567 A1 JP WO2009057567A1
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- Prior art keywords
- group
- light emitting
- light
- emitting device
- emitting element
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 125
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 125000001424 substituent group Chemical group 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 125000005013 aryl ether group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 239000002019 doping agent Substances 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 239000010703 silicon Substances 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000000101 thioether group Chemical group 0.000 claims 1
- 150000004832 aryl thioethers Chemical group 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 230000032258 transport Effects 0.000 description 32
- 238000000034 method Methods 0.000 description 24
- -1 diamine compound Chemical class 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000012044 organic layer Substances 0.000 description 15
- 230000005525 hole transport Effects 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 12
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- 239000000843 powder Substances 0.000 description 10
- 125000000168 pyrrolyl group Chemical group 0.000 description 10
- 238000000859 sublimation Methods 0.000 description 10
- 230000008022 sublimation Effects 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
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- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
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- 150000002739 metals Chemical class 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002189 fluorescence spectrum Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229910017053 inorganic salt Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000004866 oxadiazoles Chemical class 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 description 3
- WCTZZWHUWIYXND-UHFFFAOYSA-N 4-(4-tert-butylphenyl)-2-(4-methoxyphenyl)-1h-pyrrole Chemical compound C1=CC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(C)(C)C)=CN1 WCTZZWHUWIYXND-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-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
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 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 3
- 150000005054 naphthyridines Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000005041 phenanthrolines Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
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- 238000004544 sputter deposition Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 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 3
- VUKKBHGAAQDUNN-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-1-(4-methoxyphenyl)-4-nitrobutan-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)CC(C[N+]([O-])=O)C1=CC=C(C(C)(C)C)C=C1 VUKKBHGAAQDUNN-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- OTXINXDGSUFPNU-UHFFFAOYSA-N 4-tert-butylbenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C=C1 OTXINXDGSUFPNU-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- BUFLKQIQXZMRIL-UHFFFAOYSA-N [3,5-bis(4-tert-butylphenyl)-1h-pyrrol-2-yl]-phenylmethanone Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC(C=2C=CC(=CC=2)C(C)(C)C)=C(C(=O)C=2C=CC=CC=2)N1 BUFLKQIQXZMRIL-UHFFFAOYSA-N 0.000 description 2
- AFTOJASXLVFLLA-UHFFFAOYSA-N [3-(4-tert-butylphenyl)-5-(4-methoxyphenyl)-1h-pyrrol-2-yl]-(2-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(C)(C)C)=C(C(=O)C=2C(=CC=CC=2)OC)N1 AFTOJASXLVFLLA-UHFFFAOYSA-N 0.000 description 2
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
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- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001039 wet etching Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
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Abstract
Description
これらの置換基のうち、アルキル基とは、例えば、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基などの飽和脂肪族炭化水素基を示し、これは置換基を有していても有していなくてもよい。置換されている場合の追加の置換基には特に制限は無く、例えば、アルキル基、アリール基、ヘテロアリール基等を挙げることができ、この点は、以下の記載にも共通する。また、アルキル基の炭素数は特に限定されないが、通常1以上20以下の範囲、より好ましくは1以上8以下の範囲、さらに好ましくはメチル基、tert−ブチル基である。
ハロゲンとは、フッ素、塩素、臭素、およびヨウ素を示す。シアノ基、アミノ基は、置換基を有していても有していなくてもよい。置換基としては例えば上記のようなアルキル基、シクロアルキル基、アリール基、ヘテロアリール基などが挙げられる。
材料の入手しやすさや、合成の容易さを考えると上記一般式(1)のR3およびR4はともにフッ素であることが好ましい。
吸収スペクトルおよび蛍光スペクトルはそれぞれU−3200形分光光度計、F−2500形蛍光分光光度計(ともに日立製作所(株)製)を用い、4×10−6mol/Lのジクロロメタン溶液中にて測定を行った。
4−t−ブチルベンズアルデヒド12.2g、4−メトキシアセトフェノン11.3g、3M水酸化カリウム水溶液32mlとエタノール20mlの混合溶液を窒素気流下、室温で12時間撹拌した。析出した固体をろ取し、冷エタノール50mlで2回洗浄した。真空乾燥した後、3−(4−t−ブチルフェニル)−1−(4−メトキシフェニル)プロペノン17gを得た。
1H−NMR(CDCl3(d=ppm)):1.18(s, 18H), 1.35(s, 9H), 3.85(s, 3H), 6.37-6.99(m, 17H), 7.45(d, 2H), 7.87(d, 4H)。
吸収スペクトル:λmax574nm(溶媒:ジクロロメタン)
蛍光スペクトル:λmax621nm(溶媒:ジクロロメタン)。
2−ベンゾイル−3,5−ビス(4−t−ブチルフェニル)ピロールの代わりに2−(2−メトキシベンゾイル)−3,5−ビス(4−t−ブチルフェニル)ピロール381mgを用いた以外は合成例1と同様の方法で合成し、赤紫色粉末0.25gを得た。得られた粉末の1H−NMR分析結果は次の通りであり、上記で得られた赤紫色粉末が化合物〔18〕であることが確認された。
1H−NMR(CDCl3(d=ppm)):1.19(s, 18H), 1.35(s, 9H), 3.42(s, 3H), 3.85(s, 3H), 5.72(d, 1H), 6.20(t, 1H), 6.43-6.99(m, 14H), 7.43(d, 2H), 7.88(d, 4H)。
吸収スペクトル:λmax576nm(溶媒:ジクロロメタン)
蛍光スペクトル:λmax624nm(溶媒:ジクロロメタン)。
4−(4−t−ブチルフェニル)−2−(4−メトキシフェニル)ピロール300mg、2−メトキシベンゾイルクロリド201mgとトルエン10mlの混合溶液を窒素気流下、120℃で6時間加熱した。室温に冷却後、エバポレートした。エタノール20mlで洗浄し、真空乾燥した後、2−(2−メトキシベンゾイル)−3−(4−t−ブチルフェニル)−5−(4−メトキシフェニル)ピロール260mgを得た。
1H−NMR(CDCl3(d=ppm)):1.19(s, 18H), 3.42(s, 3H), 3.85(s, 6H), 5.72(d, 1H), 6.20(t, 1H), 6.42-6.97(m, 16H), 7.89(d, 4H)。
吸収スペクトル:λmax583nm(溶媒:ジクロロメタン)
蛍光スペクトル:λmax630nm(溶媒:ジクロロメタン)。
ITO透明導電膜を125nm堆積させたガラス基板(旭硝子(株)製、15Ω/□、電子ビーム蒸着品)を30×40mmに切断し、ITO導電膜をフォトリソグラフィー法によりパターン加工して、発光部分および電極引き出し部分を作製した。得られた基板をアセトン、“セミコクリン56”(フルウチ化学(株)製)で15分間超音波洗浄してから、超純水で洗浄した。続いて、イソプロピルアルコールで15分間超音波洗浄してから熱メタノールに15分間浸漬させて乾燥させた。素子を作製する直前にこの基板を1時間UV−オゾン処理し、さらに真空蒸着装置内に設置して、装置内の真空度が5×10−5Pa以下になるまで排気した。抵抗加熱法によって、まず正孔注入材料として、銅フタロシアニンを10nm、正孔輸送材料として、4,4’−ビス(N−(1−ナフチル)−N−フェニルアミノ)ビフェニルを50nm蒸着した。次に、発光材料として、ホスト材料として下記式に示すH−1を、またドーパント材料として化合物〔23〕をドープ濃度が0.5%になるように40nmの厚さに蒸着した。次に、電子輸送材料として、下記式に示すE−1を35nmの厚さに積層した。以上で形成した有機層上に、フッ化リチウムを0.5nmの厚さに蒸着した後、アルミニウムを1000nm蒸着して陰極とし、5×5mm角の素子を作製した。ここで言う膜厚は、水晶発振式膜厚モニターの表示値である。この発光素子を40mA/cm2で直流駆動したときの発光スペクトルは、ピーク波長が634nm、発光効率は6.5cd/Aの高効率高色純度赤色発光が得られた。
ドーパント材料として下記に示すD−1を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を40mA/cm2で直流駆動したときの発光スペクトルは、ピーク波長が629nm、発光効率は3.6cd/Aの高色純度低効率赤色発光が得られた。
ドーパント材料として下記に示すD−2を用いた以外は、実施例1と同様にして発光素子を作製した。この発光素子を40mA/cm2で直流駆動したときの発光スペクトルは、ピーク波長が611nm、発光効率は3.1cd/Aの低色純度低効率赤色発光が得られた。
ホスト材料、ドーパント材料、電子輸送材料として表1に示す材料を用いた以外は、実施例1と同様にして発光素子を作製した。各実施例の評価結果を表1に示す。なお、表1中、H−2およびH−3はそれぞれ下記式に示すホスト材料である。
発光層の膜厚を60nm、電子輸送層の膜厚を15nmとした以外は、実施例1と同様にして発光素子を作製した。この発光素子を40mA/cm2で直流駆動したときの発光スペクトルは、ピーク波長が634nm、発光効率は4.3cd/Aの高効率高色純度赤色発光が得られた。
電子輸送材料として下記に示すE−2を用いた以外は、実施例6と同様にして発光素子を作製した。この発光素子を40mA/cm2で直流駆動したときの発光スペクトルは、ピーク波長が634nm、発光効率は4.0cd/Aの高効率高色純度赤色発光が得られた。
電子輸送材料として下記に示すE−3を用いた以外は、実施例6と同様にして発光素子を作製した。この発光素子を40mA/cm2で直流駆動したときの発光スペクトルは、ピーク波長が633nm、発光効率は4.2cd/Aの高効率高色純度赤色発光が得られた。
ITO透明導電膜を150nm堆積させたガラス基板(旭硝子(株)製、15Ω/□、電子ビーム蒸着品)を30×40mmに切断し、フォトリソグラフィー法によって300μmピッチ(残り幅270μm)×32本のストライプ状にパターン加工した。ITOストライプの長辺方向片側は外部との電気的接続を容易にするために1.27mmピッチ(開口部幅800μm)まで広げてある。得られた基板をアセトン、“セミコクリン56”(商品名、フルウチ化学(株)製)で各々15分間超音波洗浄してから、超純水で洗浄した。続いて、イソプロピルアルコールで15分間超音波洗浄してから熱メタノールに15分間浸漬させて乾燥させた。この基板を素子を作製する直前に1時間UV−オゾン処理し、真空蒸着装置内に設置して、装置内の真空度が5×10−4Pa以下になるまで排気した。抵抗加熱法によって、まず正孔輸送材料として4,4’−ビス(N−(1−ナフチル)−N−フェニルアミノ)ビフェニルを150nm蒸着した。次に、ホスト材料としてH−1を、またドーパント材料として化合物〔23〕をドープ濃度が0.5%になるように40nmの厚さに蒸着した。次に、電子輸送材料としてE−1を35nmの厚さに積層した。ここで言う膜厚は、水晶発振式膜厚モニター表示値である。次に、厚さ50μmのコバール板にウエットエッチングによって16本の250μmの開口部(残り幅50μm、300μmピッチに相当)を設けたマスクを、真空中でITOストライプに直交するようにマスク交換し、マスクとITO基板が密着するように裏面から磁石で固定した。そしてフッ化リチウムを0.5nm蒸着した後、アルミニウムを200nm蒸着して32×16ドットマトリクス素子を作製した。本素子をマトリクス駆動させたところ、クロストークなく文字表示できた。
Claims (9)
- 一般式(1)のAr1〜Ar4のうち少なくとも1つが、無置換のフェニル基、無置換のナフチル基、またはアルキル基、アルコキシ基およびアリール基からなる群より選ばれる少なくとも1つの置換基を有するフェニル基もしくはナフチル基であることを特徴とする請求項1記載の発光素子材料。
- 一般式(1)のAr1〜Ar4のうち少なくとも1つが、無置換のフェニル基、無置換のナフチル基、またはメチル基、メトキシ基、t−ブチル基およびナフチル基からなる群より選ばれる少なくとも1つの置換基を有するフェニル基もしくはナフチル基であることを特徴とする請求項1または2記載の発光素子材料。
- 一般式(1)のAr5が無置換のフェニル基、またはアルキル基、アルコキシ基、ハロゲンおよび隣接置換基との間に形成される環構造からなる群より選ばれる少なくとも1つの置換基を有するフェニル基であることを特徴とする請求項1〜3のいずれか記載の発光素子材料。
- 一般式(1)のAr2およびAr3がアルキル基またはアルコキシ基で置換されたフェニル基であることを特徴とする請求項1または2記載の発光素子材料。
- R3とR4がともにフッ素であることを特徴とする請求項1〜5のいずれか記載の発光素子材料を含有することを特徴とする発光素子。
- 陽極と陰極の間に少なくとも発光層が存在し、電気エネルギーにより発光する発光素子であって、発光素子が請求項1〜6のいずれか記載の発光素子材料を含有することを特徴とする発光素子。
- 発光層がホスト材料とドーパント材料を有し、一般式(1)で表される発光素子材料がドーパント材料であることを特徴とする請求項7記載の発光素子。
- 発光層と陰極の間に少なくとも電子輸送層が存在し、電子輸送層が、電子受容性窒素を含み、さらに炭素、水素、窒素、酸素、ケイ素、リンの中から選ばれる元素で構成されるヘテロアリール環構造を有する化合物を含有することを特徴とする請求項8記載の発光素子。
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CN101952389B (zh) * | 2008-03-19 | 2014-01-22 | 东丽株式会社 | 发光元件材料及发光元件 |
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JP2011241160A (ja) * | 2010-05-17 | 2011-12-01 | Yamamoto Chem Inc | 色変換材料、該材料を含む組成物、該組成物を使用した色変換光学部品および該色変換光学部品を使用した発光素子 |
KR101686077B1 (ko) * | 2013-08-07 | 2016-12-13 | 제일모직 주식회사 | 유기 광전자 소자용 화합물, 이를 포함하는 유기 광전자 소자 및 상기 유기 광전자 소자를 포함하는 표시장치 |
TWI473780B (zh) | 2014-04-09 | 2015-02-21 | Nat Univ Chung Hsing | 光敏染料化合物以及染料敏化太陽能電池 |
TWI617659B (zh) * | 2015-01-31 | 2018-03-11 | Lg 化學股份有限公司 | 色彩轉換膜、其製造方法、背光單元和顯示設備 |
EP3305870B1 (en) * | 2015-05-26 | 2020-11-18 | Toray Industries, Inc. | Pyrromethene-boron complex, color-changing composition, color-changing film, light source unit including same, display, and lighting |
WO2017002707A1 (ja) * | 2015-06-29 | 2017-01-05 | 東レ株式会社 | 色変換組成物、色変換フィルム並びにそれを含む発光装置、液晶表示装置および照明装置 |
KR102515298B1 (ko) * | 2017-07-10 | 2023-03-29 | 도레이 카부시키가이샤 | 발광 소자, 그것을 포함하는 디스플레이, 조명 장치 및 센서 |
US20210061821A1 (en) * | 2018-01-26 | 2021-03-04 | Toray Industries, Inc. | Pyrromethene boron complex, color conversion composition, color conversion film, light source unit, display, illumination apparatus, and light-emitting device |
KR102148289B1 (ko) * | 2018-07-04 | 2020-08-26 | 에스에프씨주식회사 | 고효율의 유기 발광 소자 |
US11332660B2 (en) | 2018-10-15 | 2022-05-17 | Lg Chem, Ltd. | Compound, color conversion composition and color conversion film comprising same, back light unit comprising same, display device comprising same, and method for manufacturing color conversion film |
KR102650329B1 (ko) * | 2020-01-24 | 2024-03-25 | 도레이 카부시키가이샤 | 피로메텐붕소 착체, 그것을 함유하는 발광 소자, 표시 장치 및 조명 장치 |
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