JP2007049055A - Material for organic electroluminescence element, and organic electroluminescence element - Google Patents
Material for organic electroluminescence element, and organic electroluminescence element Download PDFInfo
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- JP2007049055A JP2007049055A JP2005234003A JP2005234003A JP2007049055A JP 2007049055 A JP2007049055 A JP 2007049055A JP 2005234003 A JP2005234003 A JP 2005234003A JP 2005234003 A JP2005234003 A JP 2005234003A JP 2007049055 A JP2007049055 A JP 2007049055A
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- 239000000463 material Substances 0.000 title claims abstract description 61
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 49
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 238000002347 injection Methods 0.000 claims description 48
- 239000007924 injection Substances 0.000 claims description 48
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 16
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 15
- 239000010409 thin film Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract 2
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical group C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 110
- -1 amine compound Chemical class 0.000 description 64
- 150000001875 compounds Chemical class 0.000 description 42
- 229910052782 aluminium Inorganic materials 0.000 description 18
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 13
- 229910052733 gallium Inorganic materials 0.000 description 13
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 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 5
- 239000000758 substrate Substances 0.000 description 5
- 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 5
- 238000000151 deposition Methods 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Natural products C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 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 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- JMGIDYACTFKFLK-UHFFFAOYSA-N 9,9-bis(4-iodophenyl)fluorene Chemical compound C1=CC(I)=CC=C1C1(C=2C=CC(I)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 JMGIDYACTFKFLK-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 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
- 150000004982 aromatic amines Chemical class 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
- 239000000460 chlorine Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000007733 ion plating Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- LKKPNUDVOYAOBB-UHFFFAOYSA-N naphthalocyanine Chemical class N1C(N=C2C3=CC4=CC=CC=C4C=C3C(N=C3C4=CC5=CC=CC=C5C=C4C(=N4)N3)=N2)=C(C=C2C(C=CC=C2)=C2)C2=C1N=C1C2=CC3=CC=CC=C3C=C2C4=N1 LKKPNUDVOYAOBB-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 2
- 125000005580 triphenylene group Chemical group 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
- 238000001771 vacuum deposition Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- VATMAIIQZAWLFY-UHFFFAOYSA-N (1,9,10,11,12-pentaacetyloxytriphenylen-2-yl) acetate Chemical group CC(=O)OC1=C(OC(C)=O)C(OC(C)=O)=C2C3=C(OC(C)=O)C(OC(=O)C)=CC=C3C3=CC=CC=C3C2=C1OC(C)=O VATMAIIQZAWLFY-UHFFFAOYSA-N 0.000 description 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- FXQKTVQNFVFWAA-UHFFFAOYSA-N 1,2,3,4,5,6-hexahexoxytriphenylene Chemical group CCCCCCOC1=C(OCCCCCC)C(OCCCCCC)=C2C3=C(OCCCCCC)C(OCCCCCC)=CC=C3C3=CC=CC=C3C2=C1OCCCCCC FXQKTVQNFVFWAA-UHFFFAOYSA-N 0.000 description 1
- GXDOGWCPOURDSL-UHFFFAOYSA-N 1,2,3,4,5,6-hexamethoxytriphenylene Chemical group COC1=C(OC)C(OC)=C2C3=C(OC)C(OC)=CC=C3C3=CC=CC=C3C2=C1OC GXDOGWCPOURDSL-UHFFFAOYSA-N 0.000 description 1
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical group C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- WTAPZWXVSZMMDG-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WTAPZWXVSZMMDG-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
- SJADXKHSFIMCRC-UHFFFAOYSA-N 1-n,1-n,4-n,4-n-tetrakis(4-methylphenyl)benzene-1,4-diamine Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 SJADXKHSFIMCRC-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- GUPMCMZMDAGSPF-UHFFFAOYSA-N 1-phenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1[C](C=C[CH2])C1=CC=CC=C1 GUPMCMZMDAGSPF-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- NIDFGXDXQKPZMA-UHFFFAOYSA-N 14h-benz[4,5]isoquino[2,1-a]perimidin-14-one Chemical compound C1=CC(N2C(=O)C=3C4=C(C2=N2)C=CC=C4C=CC=3)=C3C2=CC=CC3=C1 NIDFGXDXQKPZMA-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- MUNFOTHAFHGRIM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-oxadiazole Chemical compound C1=CC=C2C(C3=NN=C(O3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 MUNFOTHAFHGRIM-UHFFFAOYSA-N 0.000 description 1
- PQYIVUDIIIJJDM-UHFFFAOYSA-N 2,5-dinaphthalen-1-yl-1,3,4-thiadiazole Chemical compound C1=CC=C2C(C3=NN=C(S3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 PQYIVUDIIIJJDM-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- ZFXZGNSFTILOND-UHFFFAOYSA-L 2-carboxyquinolin-8-olate;manganese(2+) Chemical compound [Mn+2].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1.C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 ZFXZGNSFTILOND-UHFFFAOYSA-L 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UAPNUNDZDVNTDQ-UHFFFAOYSA-N 4,5-diphenyl-1,2,3-triazole Chemical compound C1=CC=CC=C1C1=NNN=C1C1=CC=CC=C1 UAPNUNDZDVNTDQ-UHFFFAOYSA-N 0.000 description 1
- YOPJQOLALJLPBS-UHFFFAOYSA-N 4,5-diphenyloxadiazole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)ON=N1 YOPJQOLALJLPBS-UHFFFAOYSA-N 0.000 description 1
- QVGVWLHVMVQIQI-UHFFFAOYSA-N 4,5-diphenylthiadiazole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)SN=N1 QVGVWLHVMVQIQI-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Pyrrole Compounds (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
本発明は平面光源や表示に使用される有機エレクトロルミネッセンス素子に関する。さらに詳しくは、低駆動電圧、高輝度、高効率、長寿命、高耐熱性を示す赤色発光用有機エレクトロルミネッセンス素子と有機エレクトロルミネッセンス素子用材料に関する。 The present invention relates to an organic electroluminescence element used for a planar light source and display. More specifically, the present invention relates to a red light-emitting organic electroluminescent element and a material for an organic electroluminescent element exhibiting low driving voltage, high luminance, high efficiency, long life, and high heat resistance.
陰極から注入された電子と陽極から注入された正孔とがこれら両極に挟まれた有機蛍光体内で再結合する際に発光するという有機エレクトロルミネッセンス（ＥＬ）素子は、固体発光型の表示素子としての用途が有望視され、近年活発に研究開発が行われている。 An organic electroluminescence (EL) element that emits light when an electron injected from a cathode and a hole injected from an anode are recombined in an organic phosphor sandwiched between these two electrodes is a solid light emitting display element. In recent years, research and development has been actively conducted.
この研究は、イーストマン・コダック社のＣ．Ｗ．Ｔａｎｇ氏らによりＡｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．，第５１巻，９１３頁，１９８７年発行に報告された有機薄膜を積層したＥＬ素子に端を発しており、この報告では、金属キレート錯体を発光層、アミン系化合物を正孔注入層に使用することで、６〜１０Ｖの直流電圧での輝度が数１０００（ｃｄ／ｍ2）、最大発光効率が１．５（ｌｍ／Ｗ）の緑色発光を得ている。現在、様々な研究機関で開発が進められている有機ＥＬ素子は、基本的にこのイーストマン・コダック社の構成を踏襲しているといえる。 This study was conducted by Eastman Kodak's C.I. W. Tang et al., Appl. Phys. Lett. 51, 913, published in 1987, which originated from an EL element with an organic thin film laminated. In this report, a metal chelate complex is used for the light emitting layer and an amine compound is used for the hole injection layer. Thus, green light emission having a luminance of several thousand (cd / m 2 ) at a DC voltage of 6 to 10 V and a maximum luminous efficiency of 1.5 (lm / W) is obtained. It can be said that the organic EL elements currently being developed by various research institutes basically follow the configuration of Eastman Kodak Company.
従来、有機ＥＬ素子に電子注入／輸送層を設けて発光効率を高めたり、駆動電圧を低くする試みがなされてきた。この場合、エキサイプレックスの形成が見られたり、高輝度の発光は得られるものの、発光寿命が短いという欠点があった。また、長時間の通電により金属電極と有機化合物層との剥離が発生したり、有機化合物層と電極が結晶化し、白濁化して発光輝度が低下するため、このような現象を防ぐ必要があった。含窒素複素環化合物を有機ＥＬ素子の構成成分として用いた例として、特許文献１にピラジン化合物、キノリン化合物、キノキサリン化合物等を用いた記載がある。しかしながら、これらの化合物は融点が低いために、有機ＥＬ素子のアモルファス薄膜層として使用しても、直ぐに結晶化が起こり、殆ど発光しなくなるなどという欠点があった。また、通電により前記した剥離が発生し、寿命が短くなるという欠点があった。 Conventionally, attempts have been made to increase the light emission efficiency or lower the driving voltage by providing an electron injection / transport layer in the organic EL element. In this case, although exciplex formation is observed and light emission with high luminance is obtained, there is a drawback that the light emission life is short. In addition, peeling between the metal electrode and the organic compound layer may occur due to prolonged energization, or the organic compound layer and the electrode may crystallize and become white turbid, resulting in a decrease in luminance. . As an example of using a nitrogen-containing heterocyclic compound as a constituent component of an organic EL device, Patent Document 1 describes the use of a pyrazine compound, a quinoline compound, a quinoxaline compound, or the like. However, since these compounds have a low melting point, there is a disadvantage that even when used as an amorphous thin film layer of an organic EL device, crystallization occurs immediately and almost no light is emitted. Further, there is a drawback that the above-described peeling occurs due to energization, and the life is shortened.
また、ジフェニルフルオレン構造を有する化合物を用いた有機ＥＬ素子については、例えば、特開平７−１４５３７２号公報、特開平７−１２６２２６号公報が知られているが、これらは正孔輸送材料として用いた例である。
本発明は、有機ＥＬ素子の構成成分として有用な含窒素複素環誘導体を提供し、この含窒素複素環誘導体を有機化合物層の少なくとも１層に用いることにより、低駆動電圧化、高輝度化、高発光効率化、長寿命化が達成できる有機ＥＬ素子を提供することを目的とする。 The present invention provides a nitrogen-containing heterocyclic derivative useful as a constituent component of an organic EL device, and by using this nitrogen-containing heterocyclic derivative in at least one layer of an organic compound layer, a low driving voltage, high luminance, An object of the present invention is to provide an organic EL device that can achieve high luminous efficiency and long life.
本発明者らは、前記目的を達成するために鋭意研究を重ねた結果、一般式［１］で表される含窒素複素環誘導体を有機ＥＬ素子の有機化合物層の少なくとも１層に用いることにより、低駆動電圧化、高輝度化、高発光効率化、長寿命化が達成できることを見出し、本発明に至った。 As a result of intensive studies to achieve the above object, the present inventors have used a nitrogen-containing heterocyclic derivative represented by the general formula [1] in at least one of the organic compound layers of the organic EL device. Thus, the inventors have found that low drive voltage, high brightness, high luminous efficiency, and long life can be achieved, and the present invention has been achieved.
すなわち、本発明は、下記一般式［１］で表される有機エレクトロルミネッセンス素子用材料に関する。
一般式［１］
General formula [1]
［式中、Ｒ1ないしＲ18は、それぞれ独立に、水素原子、ハロゲン原子、置換もしくは未置換の脂肪族炭化水素基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアルキルチオ基、シアノ基、置換もしくは未置換のアミノ基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換の芳香族炭化水素基、置換もしくは未置換の脂肪族複素環基、置換もしくは未置換の芳香族複素環基を表し、置換基同士で環を形成しても良い。ここで、Ｒ9ないしＲ18のうち少なくとも一つが、下記一般式［２］で表される置換基である。］
一般式［２］
General formula [2]
［式中、Ｒ19は水素原子、ハロゲン原子、置換もしくは未置換の芳香族炭化水素基、置換もしくは未置換の脂肪族複素環基、置換もしくは未置換の芳香族複素環基を表す。Ｘ1〜Ｘ3はそれぞれ独立に、窒素原子またはＣ−Ｒ20を表す。ここでＲ20は水素原子、ハロゲン原子、置換もしくは未置換の脂肪族炭化水素基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアルキルチオ基、シアノ基、置換もしくは未置換のアミノ基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換の芳香族炭化水素基、置換もしくは未置換の脂肪族複素環基、置換もしくは未置換の芳香族複素環基を表し、置換基同士で環を形成しても良い。］ [Wherein R 19 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aliphatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group. X 1 to X 3 each independently represent a nitrogen atom or C—R 20 . R 20 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted alkylthio group, a cyano group, a substituted or unsubstituted amino group, a substituted Or an unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aliphatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group; A ring may be formed by substituents. ]
また、本発明は、Ｒ9ないしＲ13のうち少なくとも一つ、および、Ｒ14ないしＲ18のうち少なくとも一つが、一般式［２］で表される置換基である上記有機エレクトロルミネッセンス素子用材料に関する。 In addition, the present invention provides the material for an organic electroluminescent element, wherein at least one of R 9 to R 13 and at least one of R 14 to R 18 is a substituent represented by the general formula [2]. About.
また、本発明は、陽極と陰極からなる一対の電極間に、発光層を含む少なくとも１層の有機薄膜層を有する有機エレクトロルミネッセンス素子であって、少なくとも１層が、上記有機エレクトロルミネッセンス素子用材料を含む有機エレクトロルミネッセンス素子に関する。 The present invention also provides an organic electroluminescence device having at least one organic thin film layer including a light emitting layer between a pair of electrodes consisting of an anode and a cathode, wherein at least one layer is a material for the organic electroluminescence device. The present invention relates to an organic electroluminescence device including
また、本発明は、発光層が、上記有機エレクトロルミネッセンス素子用材料を含む請求項３記載の有機エレクトロルミネッセンス素子に関する。 Moreover, this invention relates to the organic electroluminescent element of Claim 3 in which a light emitting layer contains the said organic electroluminescent element material.
また、本発明は、さらに、発光層が、リン光発光材料とを含む上記有機エレクトロルミネッセンス素子に関する。 Moreover, this invention relates to the said organic electroluminescent element in which a light emitting layer contains a phosphorescence-emitting material further.
また、本発明は、陽極と陰極からなる一対の電極間に、少なくとも、発光層と、電子注入層および／または電子輸送層とを含む有機薄膜層を有する有機エレクトロルミネッセンス素子であって、
電子注入層および／または電子輸送層が、上記有機エレクトロルミネッセンス素子用材料を含む有機エレクトロルミネッセンス素子に関する。
Further, the present invention is an organic electroluminescence device having an organic thin film layer including at least a light emitting layer and an electron injection layer and / or an electron transport layer between a pair of electrodes composed of an anode and a cathode,
An electron injection layer and / or an electron carrying layer are related with the organic electroluminescent element containing the above-mentioned organic electroluminescent element material.
また、本発明は、陽極と陰極からなる一対の電極間に、少なくとも、発光層と、正孔阻止層とを含む有機薄膜層を有する有機エレクトロルミネッセンス素子であって、
正孔阻止層が、上記有機エレクトロルミネッセンス素子用材料を含む有機エレクトロルミネッセンス素子に関する。
Further, the present invention is an organic electroluminescence device having an organic thin film layer including at least a light emitting layer and a hole blocking layer between a pair of electrodes consisting of an anode and a cathode,
The hole blocking layer relates to an organic electroluminescence device including the organic electroluminescence device material.
本発明の有機エレクトロルミネッセンス素子用材料を用いた有機エレクトロルミネッセンス素子は、従来のものと比較して低駆動電圧、長寿命であるため、壁掛けテレビ等のフラットパネルディスプレイ、複写機やプリンター等の光源、液晶ディスプレイの光源、表示板、標識灯等へ応用が考えられ、また、高耐熱性であることから車載用途等にも展開が可能である。 The organic electroluminescent element using the organic electroluminescent element material of the present invention has a low driving voltage and a long life compared to the conventional ones, so that it is a light source for a flat panel display such as a wall-mounted TV, a copying machine or a printer. It can be applied to light sources, display panels, marker lamps, etc. for liquid crystal displays, and can also be used for in-vehicle applications because of its high heat resistance.
以下、詳細にわたって本発明を説明する。一般式［１］で表される化合物において、Ｒ1ないしＲ18は、それぞれ独立に、水素原子、ハロゲン原子、置換もしくは未置換の脂肪族炭化水素基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアルキルチオ基、シアノ基、置換もしくは未置換のアミノ基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換の芳香族炭化水素基、置換もしくは未置換の脂肪族複素環基、置換もしくは未置換の芳香族複素環基を表し、置換基同士で環を形成しても良い。ここで、Ｒ9ないしＲ18のうち少なくとも一つが、一般式［２］で表される置換基である。
一般式［２］において、Ｒ19は水素原子、ハロゲン原子、置換もしくは未置換の芳香族炭化水素基、置換もしくは未置換の脂肪族複素環基、置換もしくは未置換の芳香族複素環基を表す。Ｘ1〜Ｘ3はそれぞれ独立に、窒素原子またはＣ−Ｒ20を表す。ここでＲ20は水素原子、ハロゲン原子、置換もしくは未置換の脂肪族炭化水素基、置換もしくは未置換のアルコキシル基、置換もしくは未置換のアルキルチオ基、シアノ基、置換もしくは未置換のアミノ基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換の芳香族炭化水素基、置換もしくは未置換の脂肪族複素環基、置換もしくは未置換の芳香族複素環基を表し、置換基同士で環を形成しても良い。
Hereinafter, the present invention will be described in detail. In the compound represented by the general formula [1], R 1 to R 18 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alkoxyl group, substituted or Unsubstituted alkylthio group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted aryloxy group, substituted or unsubstituted arylthio group, substituted or unsubstituted aromatic hydrocarbon group, substituted or unsubstituted It represents an aliphatic heterocyclic group or a substituted or unsubstituted aromatic heterocyclic group, and the substituents may form a ring. Here, at least one of R 9 to R 18 is a substituent represented by the general formula [2].
In the general formula [2], R 19 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aliphatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group. . X 1 to X 3 each independently represent a nitrogen atom or C—R 20 . R 20 represents a hydrogen atom, a halogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted alkoxyl group, a substituted or unsubstituted alkylthio group, a cyano group, a substituted or unsubstituted amino group, a substituted Or an unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aliphatic heterocyclic group, or a substituted or unsubstituted aromatic heterocyclic group; A ring may be formed by substituents.
ここで、本発明でいうハロゲン原子としては、弗素、塩素、臭素、ヨウ素があげられる。 Here, examples of the halogen atom in the present invention include fluorine, chlorine, bromine and iodine.
また、本発明でいう脂肪族炭化水素基としては炭素数１〜１８の脂肪族炭化水素基を指し、そのようなものとしては、アルキル基、アルケニル基、アルキニル基、シクロアルキル基があげられる。 In addition, the aliphatic hydrocarbon group referred to in the present invention refers to an aliphatic hydrocarbon group having 1 to 18 carbon atoms, and examples thereof include an alkyl group, an alkenyl group, an alkynyl group, and a cycloalkyl group.
したがって、アルキル基としては、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、イソペンチル基、ヘキシル基、ヘプチル基、オクチル基、デシル基、ドデシル基、ペンタデシル基、オクタデシル基といった炭素数１〜１８のアルキル基があげられる。 Therefore, as the alkyl group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, hexyl group, heptyl group, octyl group, C1-C18 alkyl groups, such as a decyl group, a dodecyl group, a pentadecyl group, and an octadecyl group, are mentioned.
また、アルケニル基としては、ビニル基、１−プロペニル基、２−プロペニル基、イソプロペニル基、１−ブテニル基、２−ブテニル基、３−ブテニル基、１−オクテニル基、１−デセニル基、１−オクタデセニル基といった炭素数２〜１８のアルケニル基があげられる。 Examples of the alkenyl group include vinyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-octenyl group, 1-decenyl group, 1 -An alkenyl group having 2 to 18 carbon atoms such as an octadecenyl group.
また、アルキニル基としては、エチニル基、１−プロピニル基、２−プロピニル基、１−ブチニル基、２−ブチニル基、３−ブチニル基、１−オクチニル基、１−デシニル基、１−オクタデシニル基といった炭素数２〜１８のアルキニル基があげられる。 Examples of the alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-octynyl group, 1-decynyl group and 1-octadecynyl group. Examples thereof include alkynyl groups having 2 to 18 carbon atoms.
また、シクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロオクタデシル基、２−ボルニル基、２−イソボルニル基、１−アダマンチル基といった炭素数３〜１８のシクロアルキル基があげられる。 In addition, the cycloalkyl group has a carbon number such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclooctadecyl group, 2-bornyl group, 2-isobornyl group, 1-adamantyl group. Examples thereof include 3 to 18 cycloalkyl groups.
また、本発明でいうアルコキシル基としては、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基、ｔｅｒｔ−ブトキシ基、オクチルオキシ基、ｔｅｒｔ−オクチルオキシ基、２−ボルニルオキシ基、２−イソボルニルオキシ基、１−アダマンチルオキシ基等の炭素数１〜１８のアルコキシル基があげられる。 In addition, as the alkoxyl group in the present invention, methoxy group, ethoxy group, propoxy group, butoxy group, tert-butoxy group, octyloxy group, tert-octyloxy group, 2-bornyloxy group, 2-isobornyloxy group And an alkoxyl group having 1 to 18 carbon atoms such as a 1-adamantyloxy group.
また、本発明でいうアルキルチオ基としては、メチルチオ基、エチルチオ基、ｔｅｒｔ−ブチルチオ基、ヘキシルチオ基、オクチルチオ基といった炭素数１〜１８のアルキルチオ基があげられる。 In addition, examples of the alkylthio group in the present invention include an alkylthio group having 1 to 18 carbon atoms such as a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, and an octylthio group.
また、本発明でいうアミノ基としては、ジエチルアミノ基、ジブチルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、エチルフェニルアミノ基、ジピリジルアミノ基といった炭素数６〜３０のアミノ基があげられる。 Examples of the amino group in the present invention include amino groups having 6 to 30 carbon atoms such as a diethylamino group, a dibutylamino group, a diphenylamino group, a ditolylamino group, an ethylphenylamino group, and a dipyridylamino group.
また、本発明でいうアリールオキシ基としては、フェノキシ基、４−ｔｅｒｔ−ブチルフェノキシ基、１−ナフチルオキシ基、２−ナフチルオキシ基、９−アンスリルオキシ基といった炭素数６〜３０のアリールオキシ基があげられる。 The aryloxy group referred to in the present invention is an aryloxy group having 6 to 30 carbon atoms such as a phenoxy group, 4-tert-butylphenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 9-anthryloxy group. Group.
また、本発明でいうアリールチオ基としては、フェニルチオ基、２−メチルフェニルチオ基、４−ｔｅｒｔ−ブチルフェニルチオ基といった炭素数６〜３０のアリールチオ基があげられる。 Examples of the arylthio group in the present invention include arylthio groups having 6 to 30 carbon atoms such as a phenylthio group, a 2-methylphenylthio group, and a 4-tert-butylphenylthio group.
また、本発明でいう芳香族炭化水素基としては、炭素数６〜３０の１価の単環、縮合環、環集合芳香族炭化水素基があげられる。ここで、炭素数６〜３０の単環芳香族炭化水素基としては、フェニル基、ｏ−トリル基、ｍ−トリル基、ｐ−トリル基、２，４−キシリル基、ｐ−クメニル基、メシチル基等の炭素数６〜３０の１価の単環芳香族炭化水素基があげられる。 Examples of the aromatic hydrocarbon group in the present invention include monovalent monocyclic, condensed ring, and ring-aggregated aromatic hydrocarbon groups having 6 to 30 carbon atoms. Here, as the monocyclic aromatic hydrocarbon group having 6 to 30 carbon atoms, phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, 2,4-xylyl group, p-cumenyl group, mesityl And monovalent aromatic hydrocarbon groups having 6 to 30 carbon atoms such as groups.
また、縮合環芳香族炭化水素基としては、１−ナフチル基、２−ナフチル基、１−アンスリル基、２−アンスリル基、５−アンスリル基、１−フェナンスリル基、９−フェナンスリル基、１−アセナフチル基、２−アズレニル基、１−ピレニル基、２−トリフェニレル基、１−ピレニル基、２−ピレニル基、１−ペリレニル基、２−ペリレニル基、３−ペリレニル基、２−トレフェニレニル基、２−インデニル基、１−アセナフチレニル基、２−ナフタセニル基、２−ペンタセニル基等の炭素数１０〜３０の縮合環炭化水素基があげられる。 The condensed ring aromatic hydrocarbon group includes 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 5-anthryl group, 1-phenanthryl group, 9-phenanthryl group, 1-acenaphthyl group. Group, 2-azurenyl group, 1-pyrenyl group, 2-triphenylyl group, 1-pyrenyl group, 2-pyrenyl group, 1-perylenyl group, 2-perylenyl group, 3-perenylenyl group, 2-trephenylenyl group, 2-indenyl Group, a condensed ring hydrocarbon group having 10 to 30 carbon atoms such as 1-acenaphthylenyl group, 2-naphthacenyl group and 2-pentacenyl group.
また、環集合芳香族炭化水素基としては、ｏ−ビフェニリル基、ｍ−ビフェニリル基、ｐ−ビフェニリル基、テルフェニリル基、７−（２−ナフチル）−２−ナフチル基等の炭素数１２〜３０の環集合炭化水素基があげられる。 Moreover, as a ring assembly aromatic hydrocarbon group, it is C12-30, such as o-biphenylyl group, m-biphenylyl group, p-biphenylyl group, terphenylyl group, 7- (2-naphthyl) -2-naphthyl group. Examples thereof include a ring assembly hydrocarbon group.
また、本発明でいう１価の脂肪族複素環基としては、３−イソクロマニル基、７−クロマニル基、３−クマリニル基、ピペリジノ基、モルホリノ基、２−モルホリノ基等の炭素数３〜１８の１価の脂肪族複素環基があげられる。 The monovalent aliphatic heterocyclic group referred to in the present invention has 3 to 18 carbon atoms such as 3-isochromanyl group, 7-chromanyl group, 3-coumarinyl group, piperidino group, morpholino group, 2-morpholino group and the like. And monovalent aliphatic heterocyclic groups.
また、本発明でいう１価の芳香族複素環基としては、２−フリル基、３−フリル基、２−チエニル基、３−チエニル基、２−ベンゾフリル基、２−ベンゾチエニル基、２−ピリジル基、３−ピリジル基、４−ピリジル基、２−キノリル、５−イソキノリル基、インドール基、ベンゾイミダゾール基等の炭素数３〜３０の１価の芳香族複素環基があげられる。 In addition, examples of the monovalent aromatic heterocyclic group in the present invention include 2-furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 2-benzofuryl group, 2-benzothienyl group, 2- Examples thereof include monovalent aromatic heterocyclic groups having 3 to 30 carbon atoms such as pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-quinolyl, 5-isoquinolyl group, indole group and benzimidazole group.
これら置換基は、さらに他の置換基によって置換されていても良く、また、これら置換基同士が結合し、環を形成していても良い（ただし、水素原子は置換基とはみなさない）。また、上記置換基は一例であってこれらに限定されるものではない。 These substituents may be further substituted with other substituents, and these substituents may be bonded to each other to form a ring (however, a hydrogen atom is not regarded as a substituent). Moreover, the said substituent is an example and is not limited to these.
また、より好ましい形態として、Ｒ9ないしＲ13のうち少なくとも一つ、および、Ｒ14ないしＲ18のうち少なくとも一つが、一般式［２］で表される置換基であるものが挙げられる。 Further, as a more preferred embodiment, there may be mentioned those in which at least one of R 9 to R 13 and at least one of R 14 to R 18 are a substituent represented by the general formula [2].
以下、表１に本発明の一般式［１］で表される化合物の代表例を示すが、本発明は、なんらこれらに限定されるものではない。 Hereinafter, typical examples of the compound represented by the general formula [1] of the present invention are shown in Table 1, but the present invention is not limited thereto.
ところで、有機エレクトロルミネッセンス素子は、陽極と陰極間に一層または多層の有機層を形成した素子から構成されるが、ここで、一層型有機エレクトロルミネッセンス素子とは、陽極と陰極との間に発光層のみからなる素子を指す。一方、多層型有機エレクトロルミネッセンス素子とは、発光層の他に、発光層への正孔や電子の注入を容易にしたり、発光層内での正孔と電子との再結合を円滑に行わせたりすることを目的として、正孔注入層、正孔輸送層、正孔阻止層、電子注入層などを積層させたものを指す。したがって、多層型有機エレクトロルミネッセンス素子の代表的な素子構成としては、（１）陽極／正孔注入層／発光層／陰極、（２）陽極／正孔注入層／正孔輸送層／発光層／陰極、（３）陽極／正孔注入層／発光層／電子注入層／陰極、（４）陽極／正孔注入層／正孔輸送層／発光層／電子注入層／陰極、（５）陽極／正孔注入層／発光層／正孔阻止層／電子注入層／陰極、（６）陽極／正孔注入層／正孔輸送層／発光層／正孔阻止層／電子注入層／陰極、（７）陽極／発光層／正孔阻止層／電子注入層／陰極、（８）陽極／発光層／電子注入層／陰極等の多層構成で積層した素子構成が考えられる。 By the way, an organic electroluminescence element is composed of an element in which a single layer or a multilayer organic layer is formed between an anode and a cathode. Here, a single layer type organic electroluminescence element is a light emitting layer between an anode and a cathode. The element which consists only of. On the other hand, a multi-layer organic electroluminescent element is one that facilitates the injection of holes and electrons into the light emitting layer in addition to the light emitting layer, and facilitates recombination of holes and electrons in the light emitting layer. For example, a layer in which a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, and the like are stacked is used. Therefore, typical device configurations of the multilayer organic electroluminescence device include (1) anode / hole injection layer / light emitting layer / cathode, and (2) anode / hole injection layer / hole transport layer / light emitting layer / Cathode, (3) anode / hole injection layer / light emitting layer / electron injection layer / cathode, (4) anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode, (5) anode / Hole injection layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (6) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (7 An element configuration in which a multilayer structure such as () anode / light emitting layer / hole blocking layer / electron injection layer / cathode, (8) anode / light emitting layer / electron injection layer / cathode is considered.
一般式［１］の化合物は、有機エレクトロルミネッセンス素子の有機薄膜層形成材料として全ての層で使用可能であるが、電子を注入または輸送する能力、および、発光層内で効率的に発光が得られる様に機能する能力が高いことから、より好ましくは、電子注入層、正孔阻止層、発光層の形成材料として使用するのが良い。 Although the compound of the general formula [1] can be used in all layers as a material for forming an organic thin film layer of an organic electroluminescence device, it has the ability to inject or transport electrons and can efficiently emit light within the light emitting layer. More preferably, it is used as a material for forming an electron injection layer, a hole blocking layer, and a light emitting layer.
本発明の有機エレクトロルミネッセンス素子における発光層中には、発光材料に加えて、必要に応じ他の発光材料やドーピング材料のみならず、正孔注入材料や電子注入材料を二種類以上組み合わせて使用することもできる。また、正孔注入層、発光層、電子注入層は、それぞれ二層以上の層構成により形成されても良い。 In the light emitting layer of the organic electroluminescence device of the present invention, in addition to the light emitting material, not only other light emitting materials and doping materials but also a combination of two or more types of hole injection materials and electron injection materials are used. You can also. Further, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed with a layer configuration of two or more layers.
本発明の有機エレクトロルミネッセンス素子における正孔注入・輸送材料としては、正孔を輸送する能力を持ち、陽極からの正孔注入効果、発光層または発光材料に対して優れた正孔注入効果を有し、発光層で生成した励起子の電子注入層または電子注入材料への移動を防止し、かつ薄膜形成能の優れた化合物が挙げられる。具体的には、フタロシアニン誘導体、ナフタロシアニン誘導体、ポルフィリン誘導体、トリアゾール、イミダゾール、イミダゾロン、イミダゾールチオン、ピラゾリン、ピラゾロン、テトラヒドロイミダゾール、オキサゾール、オキサジアゾール、ヒドラゾン、アシルヒドラゾン、ポリアリールアルカン、スチルベン、ブタジエン、ベンジジン型トリフェニルアミン、スチリルアミン型トリフェニルアミン、ジアミン型トリフェニルアミン等と、それらの誘導体、およびポリビニルカルバゾール、ポリシラン、導電性高分子等の高分子材料等があるが、これらに限定されるものではない。 The hole injecting / transporting material in the organic electroluminescence device of the present invention has the ability to transport holes, has an effect of injecting holes from the anode, and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, compounds that prevent migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material and have excellent thin film forming ability can be given. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, polyarylalkane, stilbene, butadiene, Benzidine-type triphenylamine, styrylamine-type triphenylamine, diamine-type triphenylamine, and derivatives thereof, and polymer materials such as polyvinyl carbazole, polysilane, and conductive polymer, but are not limited thereto. It is not a thing.
本発明の有機エレクトロルミネッセンス素子において使用できる正孔注入材料の中で、さらに効果的な正孔注入材料は、アリールアミン誘導体、フタロシアニン化合物ないしはトリフェニレン誘導体である。アリールアミン誘導体の具体例としては、トリフェニルアミン、トリトリルアミン、トリルジフェニルアミン、Ｎ，Ｎ'−ジフェニル−Ｎ，Ｎ'−ジ−ｍ−トリル−４，４'−ビフェニルジアミン、Ｎ，Ｎ，Ｎ'，Ｎ'−テトラ（ｐ−トリル）−ｐ−フェニレンジアミン、Ｎ，Ｎ，Ｎ'，Ｎ'−テトラ−ｐ−トリル−４，４'−ビフェニルジアミン、Ｎ，Ｎ'−ジフェニル−Ｎ，Ｎ'−ジ（１−ナフチル）−４，４'−ビフェニルジアミン、Ｎ，Ｎ'−ジ（４−ｎ−ブチルフェニル）−Ｎ，Ｎ'−ジ−ｐ−トリル−９，１０−フェナントレンジアミン、４，４'，４"−トリス（Ｎ−フェニル−Ｎ−ｍ−トリルアミノ）トリフェニルアミン、１，１−ビス［４−（ジ−ｐ−トリルアミノ）フェニル］シクロヘキサン等、もしくはこれらの芳香族三級アミン骨格を有したオリゴマーもしくはポリマー等があるが、これらに限定されるものではない。 Among the hole injection materials that can be used in the organic electroluminescence device of the present invention, more effective hole injection materials are arylamine derivatives, phthalocyanine compounds, or triphenylene derivatives. Specific examples of the arylamine derivative include triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N′-di-m-tolyl-4,4′-biphenyldiamine, N, N, N ', N'-tetra (p-tolyl) -p-phenylenediamine, N, N, N', N'-tetra-p-tolyl-4,4'-biphenyldiamine, N, N'-diphenyl-N, N′-di (1-naphthyl) -4,4′-biphenyldiamine, N, N′-di (4-n-butylphenyl) -N, N′-di-p-tolyl-9,10-phenanthrenediamine 4,4 ', 4 "-tris (N-phenyl-Nm-tolylamino) triphenylamine, 1,1-bis [4- (di-p-tolylamino) phenyl] cyclohexane, or aromatics thereof Has tertiary amine skeleton And there is a oligomer or polymer such as, but not limited thereto.
フタロシアニン（Ｐｃ）化合物の具体例としては、Ｈ2Ｐｃ、ＣｕＰｃ、Ｃ ｏＰｃ、ＮｉＰｃ、ＺｎＰｃ、ＰｄＰｃ、ＦｅＰｃ、ＭｎＰｃ、ＣｌＡｌＰｃ、ＣｌＧａＰｃ、ＣｌＩｎＰｃ、ＣｌＳｎＰｃ、Ｃｌ2ＳｉＰｃ、（ＨＯ）Ａ ｌＰｃ、（ＨＯ）ＧａＰｃ、ＶＯＰｃ、ＴｉＯＰｃ、ＭｏＯＰｃ、ＧａＰｃ−Ｏ−ＧａＰｃ等のフタロシアニン誘導体およびナフタロシアニン誘導体等があるが、これらに限定されるものではない。 Specific examples of the phthalocyanine (Pc) compound include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO) ) There are, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as GaPc, VOPc, TiOPc, MoOPc, and GaPc-O-GaPc.
トリフェニレン誘導体の具体例としては、ヘキサメトキシトリフェニレン、ヘキサエトキシトリフェニレン、ヘキサヘキシルオキシトリフェニレン、ヘキサベンジルオキシトリフェニレン、トリメチレンジオキシトリフェニレン、トリエチレンジオキシトリフェニレンなどのヘキサアルコキシトリフェニレン類、ヘキサフェノキシトリフェニレン、ヘキサナフチルオキシトリフェニレン、ヘキサビフェニリルオキシトリフェニレン、トリフェニレンジオキシトリフェニレンなどのヘキサアリールオキシトリフェニレン類、ヘキサアセトキシトリフェニレン、ヘキサベンゾイルオキシトリフェニレンなどのヘキサアシロキシトリフェニレン類等があるが、これらに限定されるものではない。 Specific examples of triphenylene derivatives include hexaalkoxytriphenylenes such as hexamethoxytriphenylene, hexaethoxytriphenylene, hexahexyloxytriphenylene, hexabenzyloxytriphenylene, trimethylenedioxytriphenylene, triethylenedioxytriphenylene, hexaphenoxytriphenylene, hexanaphthyl. Examples include, but are not limited to, hexaaryloxytriphenylenes such as oxytriphenylene, hexabiphenylyloxytriphenylene, and triphenylenedioxytriphenylene, and hexaacyloxytriphenylenes such as hexaacetoxytriphenylene and hexabenzoyloxytriphenylene.
本発明の有機エレクトロルミネッセンス素子における発光層を構成する発光材料としては、上記本発明の材料を用いることが好ましい。本発明の材料を発光材料として用いる場合、本発明の材料単独でもよいし、公知の発光材料と共に用いてもよい。本発明化合物が発光層以外に用いられている場合は、発光層の発光材料について、特に制限されることはなく、従来公知の発光材料の中から任意のものを選択して用いることができる。
上記従来公知の発光材料またはドーピング材料としては、ナフタレン、アントラセン、フェナントレン、ピレン、テトラセン、コロネン、クリセン、フルオレセイン、ペリレン、フタロペリレン、ナフタロペリレン、ペリノン、フタロペリノン、ナフタロペリノン、ジフェニルブタジエン、テトラフェニルブタジエン、クマリン、オキサジアゾール、アルダジン、ビスベンゾキサゾリン、ビススチリル、ジアミン、ピラジン、シクロペンタジエン、キノリン金属錯体、アミノキノリン金属錯体、ベンゾキノリン金属錯体、イミン、ジフェニルエチレン、ビニルアントラセン、ジアミノカルバゾール、ピラン、チオピラン、ポリメチン、メロシアニン、イミダゾールキレート化オキシノイド化合物、キナクリドン、ルブレン、ジケトピロロピロール等およびそれらの誘導体があるが、これらに限定されるものではない。
As the light emitting material constituting the light emitting layer in the organic electroluminescence device of the present invention, the material of the present invention is preferably used. When the material of the present invention is used as a light emitting material, the material of the present invention alone or a known light emitting material may be used. When the compound of the present invention is used other than the light emitting layer, the light emitting material of the light emitting layer is not particularly limited, and any one of conventionally known light emitting materials can be selected and used.
Examples of the conventionally known light emitting material or doping material include naphthalene, anthracene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxa Diazole, aldazine, bisbenzoxazoline, bisstyryl, diamine, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, Merocyanine, imidazole chelated oxinoid compound, quinacridone, rubrene, diketopyrrolopyrrole Le etc. and have their derivatives, but is not limited thereto.
さらに、有機エレクトロルミネッセンス素子のうち、リン光発光材料を含むことを特徴とする有機リン光発光素子は、励起三重項状態のエネルギーを発光に利用できるよう材料の選択と層構成の工夫が施されている。なお、本発明において、「有機リン光発光素子」とは、発光材料またはドーピング材料が励起三重項状態から直接的に光を放出する場合だけでなく、両極から注入された電荷の再結合によって生じた励起三重項状態を素子中で有効に発光に利用するような機構、過程を有するように設計された構成の素子全般を含む。 Furthermore, among organic electroluminescent elements, organic phosphorescent light emitting elements characterized by including a phosphorescent light emitting material are devised in material selection and layer configuration so that the energy of the excited triplet state can be used for light emission. ing. In the present invention, the “organic phosphorescent light emitting device” means not only a case where a light emitting material or a doping material directly emits light from an excited triplet state, but also a recombination of charges injected from both electrodes. In addition, all devices having a structure designed to have a mechanism and a process for effectively using the excited triplet state in the device for light emission are included.
本発明の有機エレクトロルミネッセンス素子に使用できるリン光発光材料またはドーピング材料としては、例えば有機金属錯体がある。金属原子は通常、遷移金属であり、好ましくは周期では第５周期または第６周期、族では６族から１１族、さらに好ましくは８族から１０族の元素が対象となる。具体的にはイリジウムや白金などである。また、配位子としては２−フェニルピリジンや２−（２'―ベンゾチエニル）ピリジンなどがあり、これらの配位子上の炭素原子が金属と直接結合しているのが特徴である。別の例としてはポルフィリンまたはテトラアザポルフィリン環錯体などがあり、中心金属としては白金などがあげられる。 Examples of phosphorescent materials or doping materials that can be used in the organic electroluminescence device of the present invention include organometallic complexes. The metal atom is usually a transition metal, and is preferably an element of the 5th or 6th period in the period, and from the 6th group to the 11th group in the group, and more preferably in the 8th to 10th group. Specific examples include iridium and platinum. Examples of the ligand include 2-phenylpyridine and 2- (2′-benzothienyl) pyridine, and the carbon atom on these ligands is directly bonded to the metal. Another example is a porphyrin or tetraazaporphyrin ring complex, and the central metal is platinum.
本発明の有機エレクトロルミネッセンス素子における電子注入層は、陰極より注入された電子を発光層に伝達する機能を有している。本発明の有機ＥＬ素子においては、上記本発明化合物を電子注入材料として用いることが好ましい。本発明化合物が、電子注入層以外で用いられている場合は、電子注入材料について特に制限されることはなく、従来公知の電子注入材料の中から任意のものを選択して用いることができる。 The electron injection layer in the organic electroluminescence element of the present invention has a function of transmitting electrons injected from the cathode to the light emitting layer. In the organic EL device of the present invention, the compound of the present invention is preferably used as an electron injection material. When the compound of the present invention is used in a layer other than the electron injection layer, the electron injection material is not particularly limited, and any conventionally known electron injection material can be selected and used.
上記従来公知の電子注入材料としては、金属錯体化合物または含窒素五員環誘導体があげられる。本発明に使用可能な電子注入材料の内、好ましい金属錯体化合物としては、トリス（８−ヒドロキシキノリナート）アルミニウム、トリス（２−メチル−８−ヒドロキシキノリナート）アルミニウム、トリス（５−フェニル−８−ヒドロキシキノリナート）アルミニウム、ビス（８−ヒドロキシキノリナート）（１−ナフトラート）アルミニウム、ビス（８−ヒドロキシキノリナート）（２−ナフトラート）アルミニウム、ビス（８−ヒドロキシキノリナート）（フェノラート）アルミニウム、ビス（８−ヒドロキシキノリナート）（４−シアノ−１−ナフトラート）アルミニウム、ビス（４−メチル−８−ヒドロキシキノリナート）（１−ナフトラート）アルミニウム、ビス（５−メチル−８−ヒドロキシキノリナート）（２−ナフトラート）アルミニウム、ビス（５−フェニル−８−ヒドロキシキノリナート）（フェノラート）アルミニウム、ビス（５−シアノ−８−ヒドロキシキノリナート）（４−シアノ−１−ナフトラート）アルミニウム、ビス（８−ヒドロキシキノリナート）クロロアルミニウム、ビス（８−ヒドロキシキノリナート）（ｏ−クレゾラート）アルミニウム等のアルミニウム錯体化合物、トリス（８−ヒドロキシキノリナート）ガリウム、トリス（２−メチル−８−ヒドロキシキノリナート）ガリウム、トリス（２−メチル−５−フェニル−８−ヒドロキシキノリナート）ガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）（１−ナフトラート）ガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）（２−ナフトラート）ガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）（フェノラート）ガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）（４−シアノ−１−ナフトラート）ガリウム、ビス（２、４−ジメチル−８−ヒドロキシキノリナート）（１−ナフトラート）ガリウム、ビス（２、５−ジメチル−８−ヒドロキシキノリナート）（２−ナフトラート）ガリウム、ビス（２−メチル−５−フェニル−８−ヒドロキシキノリナート）（フェノラート）ガリウム、ビス（２−メチル−５−シアノ−８−ヒドロキシキノリナート）（４−シアノ−１−ナフトラート）ガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）クロロガリウム、ビス（２−メチル−８−ヒドロキシキノリナート）（ｏ−クレゾラート）ガリウム等のガリウム錯体化合物の他、８−ヒドロキシキノリナートリチウム、ビス（８−ヒドロキシキノリナート）銅、ビス（８−ヒドロキシキノリナート）マンガン、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナート）ベリリウム、ビス（８−ヒドロキシキノリナート）亜鉛、ビス（１０−ヒドロキシベンゾ［ｈ］キノリナート）亜鉛等の金属錯体化合物があげられるが、これらに限定されるものではない。 As said conventionally well-known electron injection material, a metal complex compound or a nitrogen-containing five-membered ring derivative is mention | raise | lifted. Among the electron injection materials that can be used in the present invention, preferable metal complex compounds include tris (8-hydroxyquinolinate) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, and tris (5-phenyl). -8-hydroxyquinolinato) aluminum, bis (8-hydroxyquinolinato) (1-naphtholato) aluminum, bis (8-hydroxyquinolinato) (2-naphtholato) aluminum, bis (8-hydroxyquinolinate) ) (Phenolate) aluminum, bis (8-hydroxyquinolinate) (4-cyano-1-naphtholate) aluminum, bis (4-methyl-8-hydroxyquinolinato) (1-naphtholato) aluminum, bis (5- Methyl-8-hydroxyquinolinate) (2-naphthler) ) Aluminum, bis (5-phenyl-8-hydroxyquinolinato) (phenolate) aluminum, bis (5-cyano-8-hydroxyquinolinato) (4-cyano-1-naphtholato) aluminum, bis (8-hydroxy) Quinolinate) chloroaluminum, aluminum complex compounds such as bis (8-hydroxyquinolinate) (o-cresolate) aluminum, tris (8-hydroxyquinolinato) gallium, tris (2-methyl-8-hydroxyquinoli) Nato) gallium, tris (2-methyl-5-phenyl-8-hydroxyquinolinato) gallium, bis (2-methyl-8-hydroxyquinolinato) (1-naphtholato) gallium, bis (2-methyl-8) -Hydroxyquinolinate) (2-naphtholate) gallium, bi (2-Methyl-8-hydroxyquinolinate) (phenolate) gallium, bis (2-methyl-8-hydroxyquinolinato) (4-cyano-1-naphtholato) gallium, bis (2,4-dimethyl-8) -Hydroxyquinolinato) (1-naphtholato) gallium, bis (2,5-dimethyl-8-hydroxyquinolinato) (2-naphtholato) gallium, bis (2-methyl-5-phenyl-8-hydroxyquinolinate) Nato) (phenolate) gallium, bis (2-methyl-5-cyano-8-hydroxyquinolinate) (4-cyano-1-naphtholato) gallium, bis (2-methyl-8-hydroxyquinolinato) chlorogallium Gallium complex compounds such as bis (2-methyl-8-hydroxyquinolinate) (o-cresolate) gallium In addition, 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinate) copper, bis (8-hydroxyquinolinate) manganese, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (8-hydroxyquinone) Nolinato) zinc, metal complex compounds such as bis (10-hydroxybenzo [h] quinolinato) zinc, but are not limited thereto.
また、本発明に使用可能な電子注入材料の内、好ましい含窒素五員環誘導体としては、オキサゾール誘導体、チアゾール誘導体、オキサジアゾール誘導体、チアジアゾール誘導体、トリアゾール誘導体があげられ、具体的には、２，５−ビス（１−フェニル）−１，３，４−オキサゾール、２，５−ビス（１−フェニル）−１，３，４−チアゾール、２，５−ビス（１−フェニル）−１，３，４−オキサジアゾール、２−（４'−ｔｅｒｔ−ブチルフェニル）−５−(４"−ビフェニル)１，３，４−オキサジアゾール、２，５−ビス（１−ナフチル）−１，３，４−オキサジアゾール、１，４−ビス［２−(５ −フェニルオキサジアゾリル)］ベンゼン、１，４−ビス［２−(５−フェニルオキサジアゾリル)−４−ｔｅｒｔ−ブチルベンゼン］、２−（４'−ｔｅｒｔ− ブチルフェニル）−５−(４"−ビフェニル)−１，３，４−チアジアゾール、２，５−ビス（１−ナフチル）−１，３，４−チアジアゾール、１，４−ビス［２−(５−フェニルチアジアゾリル)］ベンゼン、２−（４'−ｔｅｒｔ−ブチルフェニル）−５−(４"−ビフェニル)−１，３，４−トリアゾール、２，５−ビス（１−ナフチル）−１，３，４−トリアゾール、１，４−ビス［２−(５−フェニルトリアゾリル)］ベンゼン等があげられるが、これらに限定されるものではない。 Among the electron injection materials that can be used in the present invention, preferable nitrogen-containing five-membered ring derivatives include oxazole derivatives, thiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, and triazole derivatives. , 5-bis (1-phenyl) -1,3,4-oxazole, 2,5-bis (1-phenyl) -1,3,4-thiazole, 2,5-bis (1-phenyl) -1, 3,4-oxadiazole, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) 1,3,4-oxadiazole, 2,5-bis (1-naphthyl) -1 , 3,4-oxadiazole, 1,4-bis [2- (5-phenyloxadiazolyl)] benzene, 1,4-bis [2- (5-phenyloxadiazolyl) -4-tert-butyl Benzene], 2 (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-thiadiazole, 2,5-bis (1-naphthyl) -1,3,4-thiadiazole, 1,4- Bis [2- (5-phenylthiadiazolyl)] benzene, 2- (4′-tert-butylphenyl) -5- (4 ″ -biphenyl) -1,3,4-triazole, 2,5-bis ( Examples include, but are not limited to, 1-naphthyl) -1,3,4-triazole, 1,4-bis [2- (5-phenyltriazolyl)] benzene and the like.
本発明の有機エレクトロルミネッセンス素子における正孔阻止層には、発光層を経由した正孔が電子注入層に達するのを阻止する能力を持ち、発光層で生成した励起子の電子注入層への拡散を防止する効果を兼ね備え、かつ薄膜形成能力の優れた化合物が挙げられる。本発明化合物が、正孔阻止層以外で用いられている場合は、正孔阻止材料について特に制限されることはなく、従来公知の正孔阻止材料の中から任意のものを選択して用いることができる。 The hole blocking layer in the organic electroluminescence device of the present invention has a capability of blocking holes that have passed through the light emitting layer from reaching the electron injection layer, and diffusion of excitons generated in the light emitting layer to the electron injection layer The compound which has the effect which prevents this, and was excellent in the thin film formation capability is mentioned. When the compound of the present invention is used in a layer other than the hole blocking layer, the hole blocking material is not particularly limited, and any one of conventionally known hole blocking materials can be selected and used. Can do.
上記従来公知の正孔阻止材料としては、例えば、２−（４−ビフェニル）−５−（４−ｔｅｒｔ−ブチルフェニル）−１，３，４−トリアゾールや２，５−ビス（１−フェニル）−１，３，４−オキサジアゾールに代表されるアゾール（含窒素五員環）類、バソクプロインに代表されるフェナントロリン誘導体、ビス（２−メチル−８−ヒドロキシキノリナート）（４−ビフェニルオキソラート）アルミニウム、ビス（２−メチル−８−ヒドロキシキノリナート）フェノラートガリウムに代表される金属錯体などの含窒素六員環類とそれらを配位子に有する金属錯体、シラシクロブテン（シロール）誘導体等があるが、これらに限定されるものではない。 Examples of the conventionally known hole blocking materials include 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3,4-triazole and 2,5-bis (1-phenyl). Azoles (nitrogen-containing five-membered rings) represented by -1,3,4-oxadiazole, phenanthroline derivatives represented by bathocuproine, bis (2-methyl-8-hydroxyquinolinate) (4-biphenyloxo) Lato) aluminum, bis (2-methyl-8-hydroxyquinolinato) phenolate six-membered rings such as metal complexes represented by gallium and metal complexes having these as ligands, silacyclobutene (silole) ) Derivatives and the like, but not limited thereto.
本発明の有機エレクトロルミネッセンス素子の陽極に用いられる導電性材料としては、４ｅＶより大きな仕事関数を持つものが適しており、炭素、アルミニウム、バナジウム、鉄、コバルト、ニッケル、タングステン、銀、金、白金、パラジウム等の金属およびそれらの合金、ＩＴＯ基板、ＮＥＳＡ基板に使用される酸化スズ、酸化インジウム等の酸化金属、さらにはポリチオフェンやポリピロール等の有機導電性樹脂等があげられる。 As the conductive material used for the anode of the organic electroluminescence device of the present invention, a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum And metals such as palladium and alloys thereof, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole.
本発明の有機エレクトロルミネッセンス素子の陰極に使用される導電性材料としては、４ｅＶより小さな仕事関数を持つものが適しており、マグネシウム、カルシウム、錫、鉛、チタニウム、イットリウム、リチウム、ルテニウム、マンガン、アルミニウム等およびそれらの合金があげられるが、これらに限定されるものではない。合金としては、マグネシウム／銀、マグネシウム／インジウム、リチウム／アルミニウム等が代表例としてあげられるが、これらに限定されるものではない。合金の比率は、蒸着源の温度、雰囲気、真空度等により制御され、適切な比率に選択される。陰極としてフッ化リチウム、フッ化マグネシウム、酸化リチウムなどのアルカリ金属、アルカリ土類金属のフッ化物、酸化物を有機層上に１ｎｍ以下の膜厚で成膜し、その上にアルミニウム、銀などの比較的導電性の高い金属を成膜してもよい。また、これら陰極は、抵抗加熱、電子線ビーム照射、スパッタリング、イオンプレーティング、コーティングなどの業界公知の方法で作成することができる。以上述べた陽極および陰極は、必要に応じて二層以上の層構成により形成されていても良い。 As the conductive material used for the cathode of the organic electroluminescence device of the present invention, a material having a work function smaller than 4 eV is suitable. Magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, Examples thereof include aluminum and the like, but are not limited thereto. Examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio. As the cathode, an alkali metal such as lithium fluoride, magnesium fluoride, or lithium oxide, a fluoride of an alkaline earth metal, or an oxide is formed on the organic layer with a film thickness of 1 nm or less, and aluminum, silver, or the like is formed thereon. A metal having a relatively high conductivity may be formed. Moreover, these cathodes can be produced by methods known in the industry such as resistance heating, electron beam irradiation, sputtering, ion plating, and coating. The anode and cathode described above may be formed with a layer structure of two or more layers as necessary.
本発明の有機エレクトロルミネッセンス素子からの発光を効率よく取り出すためには、発光を取り出す面の基板の材質が充分透明であることが望ましく、具体的には素子からの発光の発光波長領域における透過率が５０％以上、好ましくは９０％以上であることが望ましい。これら基板は、機械的、熱的強度を有し、透明であれば特に限定されるものではないが、例えば、ガラスの他、ポリエチレン、ポリエーテルスルホン、ポリプロピレン等の透明性ポリマーが推奨される。 In order to efficiently extract light emitted from the organic electroluminescence device of the present invention, it is desirable that the substrate material on the surface from which light is extracted is sufficiently transparent. Specifically, the transmittance in the emission wavelength region of light emitted from the device is desirable. Is 50% or more, preferably 90% or more. These substrates have mechanical and thermal strength and are not particularly limited as long as they are transparent. For example, in addition to glass, transparent polymers such as polyethylene, polyethersulfone, and polypropylene are recommended.
また、本発明の有機エレクトロルミネッセンス素子の各有機薄膜層の形成方法としては、真空蒸着、電子線ビーム照射、スパッタリング、プラズマ、イオンプレーティング等の乾式成膜法、もしくはスピンコーティング、ディッピング、フローコーティング等の湿式成膜法のいずれかの方法を適用することができる。各層の膜厚は特に限定されるものではないが、膜厚が厚すぎると一定の光出力を得るために大きな印加電圧が必要となり効率が低くなり、逆に膜厚が薄すぎるとピンホール等が発生し、電界を印加しても充分な発光輝度が得にくくなる。したがって、各層の膜厚は、１ｎｍから１μｍの範囲が適しているが、１０ｎｍから０．２μｍの範囲がより好ましい。 In addition, as a method for forming each organic thin film layer of the organic electroluminescence element of the present invention, dry film forming methods such as vacuum deposition, electron beam irradiation, sputtering, plasma, ion plating, or spin coating, dipping, flow coating Any one of the wet film forming methods such as the above can be applied. The film thickness of each layer is not particularly limited, but if the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in low efficiency. Conversely, if the film thickness is too thin, pinholes, etc. And it becomes difficult to obtain sufficient light emission luminance even when an electric field is applied. Accordingly, the thickness of each layer is suitably in the range of 1 nm to 1 μm, but more preferably in the range of 10 nm to 0.2 μm.
また、本発明の有機エレクトロルミネッセンス素子の温度、湿度、雰囲気等に対する安定性向上のために、素子の表面に保護層を設けたり、樹脂等により素子全体を被覆や封止を施したりしても良い。特に素子全体を被覆や封止する際には、光によって硬化する光硬化性樹脂が好適に使用される。 In addition, in order to improve the stability of the organic electroluminescent device of the present invention against temperature, humidity, atmosphere, etc., a protective layer may be provided on the surface of the device, or the entire device may be covered or sealed with a resin or the like. good. In particular, when the entire element is covered or sealed, a photocurable resin that is cured by light is preferably used.
以上述べたように、本発明の有機エレクトロルミネッセンス素子は、長寿命であるため、壁掛けテレビ等のフラットパネルディスプレイ、複写機やプリンター等の光源、液晶ディスプレイの光源、表示板、標識灯等へ応用が考えられ、また、高耐熱性であることから、車載用途等にも展開が可能であり、その工業的価値は非常に大きい。 As described above, since the organic electroluminescence element of the present invention has a long life, it can be applied to flat panel displays such as wall-mounted televisions, light sources such as copiers and printers, light sources of liquid crystal displays, display plates, and indicator lamps. In addition, since it has high heat resistance, it can be developed for in-vehicle use and the like, and its industrial value is very large.
以下、実施例にて本発明を具体的に説明するが、本発明は下記実施例に何ら限定されるものではない。はじめに、実施例に先立って本発明の有機ＥＬ素子用材料の合成例を述べる。 EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to the following Example at all. First, prior to examples, a synthesis example of the organic EL element material of the present invention will be described.
合成例１
化合物（１３）の合成方法
フラスコ中に９，９−ビス（４−ヨードフェニル）フルオレン１１ｇ、ピロール３．０ｇ、炭酸セシウム１６ｇ、ジベンジリデンアセトンパラジウム２．３ｇ、トリ−ｔ−ブチルホスフィン０．６５ｇ、キシレン８０ｍｌを入れて、１２０℃で７時間かくはんした。冷却後、メタノールに注ぎ、生じた沈殿をろ過し集めた。沈殿をシリカゲルでカラム精製をおこなった後、昇華精製した。ＮＭＲ、マススペクトルによって化合物の生成を確認した。
Synthesis example 1
Synthesis method of compound (13) In a flask, 9,9-bis (4-iodophenyl) fluorene 11 g, pyrrole 3.0 g, cesium carbonate 16 g, dibenzylideneacetone palladium 2.3 g, tri-t-butylphosphine 0.65 g Then, 80 ml of xylene was added and stirred at 120 ° C. for 7 hours. After cooling, it was poured into methanol, and the resulting precipitate was collected by filtration. The precipitate was subjected to column purification with silica gel and then purified by sublimation. Formation of the compound was confirmed by NMR and mass spectrum.
合成例２
化合物（２８）の合成方法
フラスコ中にフラスコ中に９，９−ビス（４−ヨードフェニル）フルオレン２２ｇ、２−フェニルベンゾイミダゾール１９ｇ、ヨウ化銅０．７６ｇ、１，１０−フェナントロリン１．４ｇ、炭酸セシウム２９ｇ、ジメチルホルムアミド４０ｍｌを入れて、１１０℃で１２時間かくはんした。冷却後、反応液をろ過し、ろ液を濃縮し固体を得た。得られた個体をシリカゲルでカラム精製を行った後、昇華精製した。ＮＭＲ、マススペクトルによって化合物の生成を確認した。
Synthesis example 2
Synthesis method of compound (28) In a flask, 9,9-bis (4-iodophenyl) fluorene 22g, 2-phenylbenzimidazole 19g, copper iodide 0.76g, 1,10-phenanthroline 1.4g, 29 g of cesium carbonate and 40 ml of dimethylformamide were added and stirred at 110 ° C. for 12 hours. After cooling, the reaction solution was filtered, and the filtrate was concentrated to obtain a solid. The obtained solid was subjected to column purification with silica gel and then purified by sublimation. Formation of the compound was confirmed by NMR and mass spectrum.
以下に本発明の化合物を用いた実施例を示すが、本発明は下記実施例に限定されるものではない。実施例においては、特に断りのない限り、混合比は全て重量比を示す。蒸着（真空蒸着）は１０-6Ｔｏｒｒの真空中で、基板加熱、冷却等の温度制御なしの条件下で行った。また、素子の発光特性評価においては、電極面積２ｍｍ×２ｍｍの有機ＥＬ素子の特性を測定した。測定は１Ｖずつ上昇しながら各電圧で電流、輝度、色度を記録した。最大発光輝度および効率は各電圧ごとの測定値の最大値であり、その時の電圧は素子により異なる。 Examples using the compounds of the present invention are shown below, but the present invention is not limited to the following examples. In the examples, all mixing ratios are weight ratios unless otherwise specified. Vapor deposition (vacuum deposition) was performed in a vacuum of 10 −6 Torr and under conditions without temperature control such as substrate heating and cooling. In the evaluation of the light emission characteristics of the element, the characteristics of an organic EL element having an electrode area of 2 mm × 2 mm were measured. The measurement recorded current, luminance, and chromaticity at each voltage while increasing by 1V. The maximum light emission luminance and efficiency are the maximum values measured for each voltage, and the voltage at that time varies depending on the element.
実施例１
洗浄したＩＴＯ電極付きガラス板上に、Ｎ，Ｎ'―（１―ナフチル）―Ｎ，Ｎ'―ジフェニル―１，１'―ビフェニル-４，４'―ジアミン（ＮＰＤ）を真空蒸着して膜厚４０ｎｍの正孔注入層を得た。次いで、トリス（８−ヒドロキシキノリナート）アルミニウム（Ａｌｑ３）と下記化合物（Ｄ１）を９８:２の比率で共蒸着して、膜厚４０ｎｍの発光層を作成し、次いで化合物（３１）を真空蒸着して膜厚３０ｎｍの電子注入層を作成した。その上に、フッ化リチウムを０．７ｎｍ、次いでアルミニウムを２００ｎｍ真空蒸着することで電極を形成して、有機エレクトロルミネッセンス素子を得た。この素子は、直流電圧５Ｖでの発光輝度４３０（ｃｄ／ｍ2）、最大発光輝度９３６００（ｃｄ／ｍ2）の発光が得られた。また、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命は５１００時間であった。
Example 1
N, N '-(1-naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine (NPD) is vacuum-deposited on a cleaned glass plate with an ITO electrode. A hole injection layer having a thickness of 40 nm was obtained. Next, tris (8-hydroxyquinolinato) aluminum (Alq3) and the following compound (D1) were co-evaporated at a ratio of 98: 2, to form a light-emitting layer having a thickness of 40 nm, and then the compound (31) was vacuum-treated. An electron injection layer having a thickness of 30 nm was formed by vapor deposition. An electrode was formed thereon by vacuum-depositing lithium fluoride at 0.7 nm and then aluminum at 200 nm to obtain an organic electroluminescence element. This device emitted light having a light emission luminance of 430 (cd / m 2 ) and a maximum light emission luminance of 93600 (cd / m 2 ) at a DC voltage of 5V. Further, the half-life when driven at a constant current at an emission luminance of 500 (cd / m 2 ) was 5100 hours.
実施例２〜実施例７
化合物（３１）の代わりに表２に示す化合物を用いる以外は、全て実施例１と同様の方法で有機ＥＬ素子を作成した。これらの素子の直流電圧５Ｖでの発光輝度、最大発光輝度、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命を併せて表２に示す。
Example 2 to Example 7
An organic EL device was produced in the same manner as in Example 1 except that the compound shown in Table 2 was used instead of the compound (31). Table 2 shows the light emission luminance at a DC voltage of 5 V, the maximum light emission luminance, and the half-life when these elements are driven at a constant current at an emission luminance of 500 (cd / m 2 ).
比較例１
化合物（３１）の代わりにＡｌｑ３を用いる以外は、全て実施例１と同様の方法で有機ＥＬ素子を作成した。この素子の直流電圧５Ｖでの発光輝度、最大発光輝度、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命を併せて表２に示す。
Comparative Example 1
An organic EL device was produced in the same manner as in Example 1 except that Alq3 was used instead of the compound (31). Table 2 shows the light emission luminance at a DC voltage of 5 V, the maximum light emission luminance, and the half-life when the device is driven at a constant current at a light emission luminance of 500 (cd / m 2 ).
実施例８
洗浄したＩＴＯ電極付きガラス板上に、ＮＰＤを真空蒸着して膜厚４０ｎｍの正孔注入層を得た。次いで、下記ＣＢＰと下記化合物（Ｄ２）を９３：７の比率で共蒸着して、膜厚４０ｎｍの発光層を作成し、次いで化合物（２９）を真空蒸着して膜厚１０ｎｍの正孔ブロッキング層、さらにＡｌｑ３を真空蒸着して膜厚３０ｎｍの電子注入層を作成した。その上に、フッ化リチウムを０．７ｎｍ、次いでアルミニウムを２００ｎｍ真空蒸着することで電極を形成して、有機燐光発光素子を得た。この素子は、直流電圧１０Ｖでの発光輝度１２５００（ｃｄ／ｍ2）、最大発光輝度９５４００（ｃｄ／ｍ2）、発光効率４２（ｃｄ／Ａ）の発光が得られた。また、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命は４８００時間であった。
Example 8
On the washed glass plate with the ITO electrode, NPD was vacuum-deposited to obtain a hole injection layer having a thickness of 40 nm. Next, the following CBP and the following compound (D2) are co-evaporated at a ratio of 93: 7 to form a light emitting layer having a thickness of 40 nm, and then the compound (29) is vacuum evaporated to form a hole blocking layer having a thickness of 10 nm. Further, Alq3 was vacuum-deposited to form an electron injection layer having a thickness of 30 nm. An electrode was formed thereon by vacuum-depositing lithium fluoride at 0.7 nm and then aluminum at 200 nm to obtain an organic phosphorescent device. This device emitted light with a luminance of 12500 (cd / m 2 ), a maximum luminance of 95400 (cd / m 2 ), and a luminous efficiency of 42 (cd / A) at a DC voltage of 10V. The half life when driven at a constant current at an emission luminance of 500 (cd / m 2 ) was 4800 hours.
実施例９〜実施例１２
化合物（２９）の代わりに表３に示す化合物を用いる以外は、全て実施例８と同様の方法で有機燐光発光素子を作成した。これらの素子の直流電圧１０Ｖでの発光輝度、最大発光輝度、発光効率、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命を併せて表３に示す。
Example 9 to Example 12
An organic phosphorescent light emitting device was produced in the same manner as in Example 8 except that the compound shown in Table 3 was used instead of the compound (29). Table 3 shows the light emission luminance at a DC voltage of 10 V, the maximum light emission luminance, the light emission efficiency, and the half life when these elements are driven at a constant current of 500 (cd / m 2 ).
比較例２
化合物（２９）の代わりに下記比較化合物Ａを用いる以外は、全て実施例８と同様の方法で有機燐光発光素子を作成した。この素子の直流電圧１０Ｖでの発光輝度、最大発光輝度、発光効率、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命を併せて表３に示す。
Comparative Example 2
An organic phosphorescent light emitting device was prepared in the same manner as in Example 8 except that the following comparative compound A was used instead of the compound (29). Table 3 shows the light emission luminance at a DC voltage of 10 V, the maximum light emission luminance, the light emission efficiency, and the half-life when the device is driven at a constant current at a light emission luminance of 500 (cd / m 2 ).
実施例１３
洗浄したＩＴＯ電極付きガラス板上に、ＮＰＤを真空蒸着して膜厚４０ｎｍの正孔注入層を得た。次いで、化合物（３７）と化合物（Ｄ１）を９８：２の比率で共蒸着して、膜厚４０ｎｍの発光層を作成し、次いでＡｌｑ３を真空蒸着して膜厚３０ｎｍの電子注入層を作成した。その上に、フッ化リチウムを０．７ｎｍ、次いでアルミニウムを２００ｎｍ真空蒸着することで電極を形成して、有機燐光発光素子を得た。この素子は、直流電圧５Ｖでの発光輝度３６０（ｃｄ／ｍ2）、最大発光輝度８７６００（ｃｄ／ｍ2ときの半減寿命は４５００時間であった。
Example 13
On the washed glass plate with the ITO electrode, NPD was vacuum-deposited to obtain a hole injection layer having a thickness of 40 nm. Next, the compound (37) and the compound (D1) were co-evaporated at a ratio of 98: 2 to prepare a light emitting layer with a thickness of 40 nm, and then Alq3 was vacuum evaporated to prepare an electron injection layer with a thickness of 30 nm. . An electrode was formed thereon by vacuum-depositing lithium fluoride at 0.7 nm and then aluminum at 200 nm to obtain an organic phosphorescent device. This device had a light emission luminance of 360 (cd / m 2) at a DC voltage of 5 V and a half life of 4500 hours when the maximum light emission luminance was 87600 (cd / m 2).
実施例１４〜実施例１７
化合物（３７）の代わりに表４に示す化合物を用いる以外は、全て実施例１と同様の方法で有機ＥＬ素子を作成した。これらの素子の直流電圧５Ｖでの発光輝度、最大発光輝度、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命を併せて表４に示す。
Examples 14 to 17
An organic EL device was produced in the same manner as in Example 1 except that the compound shown in Table 4 was used instead of the compound (37). Emission luminance at a DC voltage of 5V of these elements, shown maximum emission luminance, together half life when the constant current driving with emission luminance 500 (cd / m 2) in Table 4.
比較例３
化合物（３７）の代わりにＡｌｑ３を用いる以外は、全て実施例１と同様の方法で有機ＥＬ素子を作成した。この素子の直流電圧５Ｖでの発光輝度、最大発光輝度、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命を併せて表４に示す。
Comparative Example 3
An organic EL device was produced in the same manner as in Example 1 except that Alq3 was used instead of the compound (37). Table 4 shows the light emission luminance at a DC voltage of 5 V, the maximum light emission luminance, and the half-life when the device is driven at a constant current at a light emission luminance of 500 (cd / m 2 ).
実施例１８
洗浄したＩＴＯ電極付きガラス板上に、ＮＰＤを真空蒸着して膜厚４０ｎｍの正孔注入層を得た。次いで、化合物（２８）と化合物（Ｄ２）を９３：７の比率で共蒸着して、膜厚４０ｎｍの発光層を作成し、次いで化合物（１７）を真空蒸着して膜厚１０ｎｍの正孔ブロッキング層、さらにＡｌｑ３を真空蒸着して膜厚３０ｎｍの電子注入層を作成した。その上に、フッ化リチウムを０．７ｎｍ、次いでアルミニウムを２００ｎｍ真空蒸着することで電極を形成して、有機燐光発光素子を得た。この素子は、直流電圧１０Ｖでの発光輝度１３５００（ｃｄ／ｍ2）、最大発光輝度９７９００（ｃｄ／ｍ2）、発光効率４６（ｃｄ／Ａ）の発光が得られた。また、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命は３９００時間であった。
Example 18
On the washed glass plate with the ITO electrode, NPD was vacuum-deposited to obtain a hole injection layer having a thickness of 40 nm. Next, the compound (28) and the compound (D2) are co-evaporated at a ratio of 93: 7 to form a light emitting layer with a thickness of 40 nm, and then the compound (17) is vacuum evaporated to form a hole blocking with a thickness of 10 nm. The layer and further Alq3 were vacuum deposited to form an electron injection layer with a thickness of 30 nm. An electrode was formed thereon by vacuum-depositing lithium fluoride at 0.7 nm and then aluminum at 200 nm to obtain an organic phosphorescent device. This device emitted light with a luminance of 13500 (cd / m 2 ), a maximum luminance of 97900 (cd / m 2 ), and a luminous efficiency of 46 (cd / A) at a DC voltage of 10V. Further, the half-life when driven at a constant current at an emission luminance of 500 (cd / m 2 ) was 3900 hours.
実施例１９〜実施例２２
化合物（２８）の代わりに表５に示す化合物を用いる以外は、全て実施例８と同様の方法で有機燐光発光素子を作成した。これらの素子の直流電圧１０Ｖでの発光輝度、最大発光輝度、発光効率、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命を併せて表５に示す。
Examples 19 to 22
An organic phosphorescent light emitting device was prepared in the same manner as in Example 8 except that the compound shown in Table 5 was used instead of the compound (28). Table 5 shows the light emission luminance at a DC voltage of 10 V, the maximum light emission luminance, the light emission efficiency, and the half life when these elements are driven at a constant current of 500 (cd / m 2 ).
比較例４
化合物（２８）の代わりに下記比較化合物Ｂを用いる以外は、全て実施例８と同様の方法で有機燐光発光素子を作成した。この素子の直流電圧１０Ｖでの発光輝度、最大発光輝度、発光効率、発光輝度５００（ｃｄ／ｍ2）で定電流駆動したときの半減寿命を併せて表５に示す。
Comparative Example 4
An organic phosphorescent light emitting device was prepared in the same manner as in Example 8 except that the following comparative compound B was used instead of the compound (28). Table 5 shows the light emission luminance at a DC voltage of 10 V, the maximum light emission luminance, the light emission efficiency, and the half life when the device is driven at a constant current at a light emission luminance of 500 (cd / m 2 ).
以上述べた実施例から明らかなように、本発明の含窒素複素環誘導体を有機化合物層を用いることにより、低駆動電圧化、高輝度化、高発光効率化、長寿命化が達成できた。 As is clear from the examples described above, by using the organic compound layer for the nitrogen-containing heterocyclic derivative of the present invention, low driving voltage, high luminance, high luminous efficiency, and long life could be achieved.
Claims (7)
一般式［１］
一般式［２］
General formula [1]
General formula [2]
電子注入層および／または電子輸送層が、請求項１または２記載の有機エレクトロルミネッセンス素子用材料を含む有機エレクトロルミネッセンス素子。 An organic electroluminescent device having an organic thin film layer including at least a light emitting layer and an electron injection layer and / or an electron transport layer between a pair of electrodes consisting of an anode and a cathode,
The organic electroluminescent element in which an electron injection layer and / or an electron carrying layer contain the organic electroluminescent element material of Claim 1 or 2.
正孔阻止層が、請求項１または２記載の有機エレクトロルミネッセンス素子用材料を含む有機エレクトロルミネッセンス素子。
An organic electroluminescence device having an organic thin film layer including at least a light emitting layer and a hole blocking layer between a pair of electrodes consisting of an anode and a cathode,
The organic electroluminescent element in which a hole-blocking layer contains the material for organic electroluminescent elements of Claim 1 or 2.
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| KR101030020B1 (en) | 2008-09-02 | 2011-04-20 | 제일모직주식회사 | Pyrrole compounds and organic photoelectric device including the same |
| US8603646B2 (en) | 2008-09-02 | 2013-12-10 | Cheil Industries, Inc. | Pyrrole compound and organic photoelectric device including the same |
| WO2010076984A2 (en) * | 2008-12-29 | 2010-07-08 | 제일모직 주식회사 | Novel compounds for an organic photoelectric device, and organic photoelectric device comprising same |
| WO2010076984A3 (en) * | 2008-12-29 | 2010-08-26 | 제일모직 주식회사 | Novel compounds for an organic photoelectric device, and organic photoelectric device comprising same |
| US8815418B2 (en) | 2009-05-15 | 2014-08-26 | Cheil Industries, Inc. | Compound including fluorenyl group for organic photoelectric device and organic photoelectric device including the same |
| JP2013510889A (en) * | 2009-11-17 | 2013-03-28 | メルク パテント ゲーエムベーハー | Materials for organic electroluminescent devices |
| US11760734B2 (en) | 2009-11-17 | 2023-09-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| JP2013510890A (en) * | 2009-11-17 | 2013-03-28 | メルク パテント ゲーエムベーハー | Materials for organic electroluminescent devices |
| KR101839627B1 (en) | 2009-11-17 | 2018-03-16 | 메르크 파텐트 게엠베하 | Materials for organic light emitting devices |
| US10233159B2 (en) | 2009-11-17 | 2019-03-19 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| US10981880B2 (en) | 2009-11-17 | 2021-04-20 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| US9199972B2 (en) | 2009-11-17 | 2015-12-01 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| US9187456B2 (en) | 2009-11-17 | 2015-11-17 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
| JP2011168544A (en) * | 2010-02-19 | 2011-09-01 | Chemiprokasei Kaisha Ltd | Pyrrole compound and organic electroluminescent element using the same |
| JP2012067093A (en) * | 2010-08-27 | 2012-04-05 | Semiconductor Energy Lab Co Ltd | Fluorene derivative, organic compound, and light-emitting element using the compound, light-emitting device, and electronic apparatus |
| US8927120B2 (en) | 2011-06-22 | 2015-01-06 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| JP2013065863A (en) * | 2012-10-31 | 2013-04-11 | Konica Minolta Holdings Inc | Organic electroluminescent element, display device and lighting system |
| KR101546141B1 (en) * | 2013-09-10 | 2015-08-20 | 한국생산기술연구원 | Luminescent organic compound containing fluorene group, and organic light emitting diode including the same |
| EP4037000A1 (en) * | 2014-07-21 | 2022-08-03 | Merck Patent GmbH | Materials for electronic devices |
| WO2016068478A3 (en) * | 2014-10-30 | 2016-08-04 | 주식회사 엘지화학 | Cyclic compound and organic light-emitting element comprising same |
| KR101787195B1 (en) * | 2014-10-30 | 2017-10-18 | 주식회사 엘지화학 | Cyclic compound and organic light emitting device comprising the same |
| CN107074784A (en) * | 2014-10-30 | 2017-08-18 | 株式会社Lg化学 | Cyclic compound and the organic illuminating element comprising it |
| JP2017533893A (en) * | 2014-10-30 | 2017-11-16 | エルジー・ケム・リミテッド | Ring compound and organic light emitting device including the same |
| US10431748B2 (en) | 2014-10-30 | 2019-10-01 | Lg Chem, Ltd. | Cyclic compound and organic light-emitting element comprising same |
| EP3872074A1 (en) | 2015-05-12 | 2021-09-01 | Novaled GmbH | Organic light-emitting diode comprising different matrix compounds in the first and second electron transport layer |
| KR20180005199A (en) * | 2015-05-12 | 2018-01-15 | 노발레드 게엠베하 | An organic light emitting diode comprising different matrix compounds in the first electron transporting layer and the second electron transporting layer |
| KR102652730B1 (en) | 2015-05-12 | 2024-03-28 | 노발레드 게엠베하 | Organic light emitting diode comprising different matrix compounds in the first electron transport layer and the second electron transport layer |
| EP3093288A1 (en) * | 2015-05-12 | 2016-11-16 | Novaled GmbH | Organic light-emitting diode comprising different matrix compounds in the first and second electron transport layer |
| WO2016180891A1 (en) * | 2015-05-12 | 2016-11-17 | Novaled Gmbh | Organic light-emitting diode comprising different matrix compounds in the first and second electron transport layer |
| US11081652B2 (en) | 2015-05-12 | 2021-08-03 | Novaled Gmbh | Organic light-emitting diode comprising different matrix compounds in the first and second electron transport layer |
| KR101859273B1 (en) | 2015-05-14 | 2018-05-17 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| US11673875B2 (en) | 2015-09-09 | 2023-06-13 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectric diode, and display device |
| CN109071465A (en) * | 2016-03-28 | 2018-12-21 | 株式会社Lg化学 | A kind of compound and the organic electronic element comprising it |
| CN108604642B (en) * | 2016-04-28 | 2020-01-17 | 株式会社Lg化学 | Organic light emitting element |
| CN108603106A (en) * | 2016-04-28 | 2018-09-28 | 株式会社Lg化学 | Organic luminescent device |
| US11723268B2 (en) | 2016-04-28 | 2023-08-08 | Lg Chem, Ltd. | Organic light-emitting element |
| CN108604642A (en) * | 2016-04-28 | 2018-09-28 | 株式会社Lg化学 | Organic illuminating element |
| CN107353281A (en) * | 2016-05-10 | 2017-11-17 | 株式会社Lg化学 | New compound and the organic illuminating element for including it |
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