CN104471734A - 有机电场发光元件 - Google Patents
有机电场发光元件 Download PDFInfo
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- CN104471734A CN104471734A CN201380037591.3A CN201380037591A CN104471734A CN 104471734 A CN104471734 A CN 104471734A CN 201380037591 A CN201380037591 A CN 201380037591A CN 104471734 A CN104471734 A CN 104471734A
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- Prior art keywords
- aromatic
- layer
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- organic
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- -1 carbazole compound Chemical class 0.000 claims abstract description 90
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 80
- 239000012044 organic layer Substances 0.000 claims abstract description 20
- 239000000758 substrate Substances 0.000 claims abstract description 13
- 239000010410 layer Substances 0.000 claims description 159
- 229910052799 carbon Inorganic materials 0.000 claims description 58
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 51
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 230000005540 biological transmission Effects 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000002019 doping agent Substances 0.000 claims description 18
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 230000004888 barrier function Effects 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 230000005684 electric field Effects 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 238000003475 lamination Methods 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 4
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 abstract description 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 description 80
- 150000001875 compounds Chemical class 0.000 description 54
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 238000004020 luminiscence type Methods 0.000 description 23
- 238000002347 injection Methods 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 17
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 16
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
- 239000004411 aluminium Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 12
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 12
- 150000004826 dibenzofurans Chemical class 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000004305 biphenyl Substances 0.000 description 9
- 235000010290 biphenyl Nutrition 0.000 description 9
- 230000005284 excitation Effects 0.000 description 9
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- 150000004866 oxadiazoles Chemical class 0.000 description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229930192474 thiophene Natural products 0.000 description 6
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 5
- 241001597008 Nomeidae Species 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 150000002469 indenes Chemical class 0.000 description 5
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- YFIJJNAKSZUOLT-UHFFFAOYSA-N Anthanthrene Chemical compound C1=C(C2=C34)C=CC=C2C=CC3=CC2=CC=CC3=CC=C1C4=C32 YFIJJNAKSZUOLT-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241000254158 Lampyridae Species 0.000 description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- 150000002475 indoles Chemical class 0.000 description 4
- 150000003233 pyrroles Chemical class 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 4
- 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 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- BMQDAIUNAGXSKR-UHFFFAOYSA-N (3-hydroxy-2,3-dimethylbutan-2-yl)oxyboronic acid Chemical compound CC(C)(O)C(C)(C)OB(O)O BMQDAIUNAGXSKR-UHFFFAOYSA-N 0.000 description 3
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 3
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 150000002220 fluorenes Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QSQIGGCOCHABAP-UHFFFAOYSA-N hexacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C21 QSQIGGCOCHABAP-UHFFFAOYSA-N 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000007978 oxazole derivatives Chemical class 0.000 description 3
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 3
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GVSPXQVUXHMUMA-MDWZMJQESA-N (e)-3-(3,5-ditert-butyl-4-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)\C=C\C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GVSPXQVUXHMUMA-MDWZMJQESA-N 0.000 description 2
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 2
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class 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 2
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 2
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 description 2
- ILFYOWGJBKEMSK-UHFFFAOYSA-N 10h-phenoselenazine Chemical compound C1=CC=C2NC3=CC=CC=C3[Se]C2=C1 ILFYOWGJBKEMSK-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- WKAXDAMWMOBXMP-UHFFFAOYSA-N 2,3-diphenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=C1 WKAXDAMWMOBXMP-UHFFFAOYSA-N 0.000 description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 2
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 2
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
- BWRMZQGIDWILAU-UHFFFAOYSA-N 4,6-diphenylpyrimidine Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=NC=N1 BWRMZQGIDWILAU-UHFFFAOYSA-N 0.000 description 2
- HHVGZHHLRBNWAD-UHFFFAOYSA-N 4,6-diphenyltriazine Chemical compound C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=NN=N1 HHVGZHHLRBNWAD-UHFFFAOYSA-N 0.000 description 2
- YUXBNNVWBUTOQZ-UHFFFAOYSA-N 4-phenyltriazine Chemical compound C1=CC=CC=C1C1=CC=NN=N1 YUXBNNVWBUTOQZ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-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
- DZLJRUWNLKQWIT-UHFFFAOYSA-N C1C=CC2=CC=CC=C12.[Si] Chemical class C1C=CC2=CC=CC=C12.[Si] DZLJRUWNLKQWIT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- QYOXHEQDXMYNPP-UHFFFAOYSA-N O1CC=CC2=CC=CC=C12.[S] Chemical compound O1CC=CC2=CC=CC=C12.[S] QYOXHEQDXMYNPP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Chemical class 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-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
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- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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Abstract
本发明提供一种改善元件的发光效率,充分确保驱动稳定性,且具有简略的构成的有机电场发光元件(有机EL元件)。本发明的有机电场发光元件是在积层于基板上的阳极与阴极之间具有多个有机层的有机电场发光元件,且在该有机层中的至少一个层中含有咔唑化合物,上述咔唑化合物具有2个~3个的咔唑环与二苯并呋喃或二苯并噻吩环以1位与4位键结而成的结构且由下述通式(1)所表示。式(1)中,A为n价的芳香族烃基或芳香族杂环基,n为2或3的整数,X为氧或硫。
Description
技术领域
本发明涉及一种使用包含具有特定结构的咔唑化合物的有机电场发光元件用材料的有机电场发光元件,详细而言,本发明涉及一种对包含有机化合物的发光层施加电场而发出光的薄膜型元件(film type device)。
背景技术
通常,有机电场发光元件(以下,称为有机电致发光(electroluminescence,EL)元件)的最简单的构造包含发光层及夹持该层的一对对向电极。即,有机EL元件是利用如下现象:若在两电极间施加电场,则自阴极注入电子,自阳极注入空穴,该些在发光层中再结合而发出光。
近年来,越发广泛地进行使用有机薄膜的有机EL元件的开发。尤其为了提高发光效率,以提高载子(carrier)自电极的注入效率为目的而进行电极的种类的最佳化,藉由在电极间以薄膜的形式设置有包含芳香族二胺的空穴传输层与包含三(8-羟基喹啉)铝错合物(以下,称为Alq3)的发光层的元件的开发,而与现有的使用蒽等的单晶的元件相比发光效率得到大幅度改善,因此以对具有自发光·高速响应性(responsiveness)等特征的高性能平板(flat panel)的实用化为目标而不断推进。
另外,作为提高元件的发光效率的尝试,也研究不使用萤光而使用磷光。以上述的设置有包含芳香族二胺的空穴传输层与包含Alq3的发光层的元件为代表的多种元件是利用萤光发光,但藉由使用磷光发光、即利用来自三重态激发状态的发光,而与现有的使用萤光(单态)的元件相比,期待3倍~4倍左右的效率的提高。为了此目的而研究以香豆素衍生物或二苯甲酮衍生物作为发光层,但仅获得极低的亮度。另外,作为利用三重态激发状态的尝试,研究使用铕错合物,但其也未达成高效率的发光。近年来,如专利文献1中所列举般以发光的高效率化或长寿命化为目的而以铱错合物等有机金属错合物为中心进行大量研究。
现有技术文献
专利文献
专利文献1WO01/041512A1
专利文献2日本专利特开2001-313178号公报
专利文献3US2006/0054861A1
专利文献4日本专利特开2009-267257号公报
专利文献5日本专利特开2009-267255号公报
专利文献6WO2007/119816A1
专利文献7日本专利特开2012-49518号公报
对于获得高发光效率而言,重要的是与上述掺杂剂材料(dopant material)同时使用的主体材料(hostmaterials)。所提出的代表性的主体材料可列举专利文献2中所介绍的咔唑化合物的4,4′-二(9-咔唑基)联苯(CBP)。CBP在用作以三(2-苯基吡啶)铱错合物(Ir(ppy)3)为代表的绿色磷光发光材料的主体材料的情况下,由于CBP的容易使空穴流动且不易使电子流动的特性,而电荷注入传输平衡(balance)被破坏,过剩的空穴流出至电子传输层侧,结果源自Ir(ppy)3的发光效率降低。
如上所述,对于有机EL元件,为了获得高的发光效率,而必须具有高的三重态激发能量(triplet excitation energy),且在两电荷(空穴·电子)的注入传输特性方面获得了平衡的主体材料。进而,理想的是电化学性稳定,且具备高的耐热性以及优异的非晶质(amorphous)稳定性的化合物,而谋求进一步的改良。
专利文献3中,作为有机EL元件的主体材料揭示有如下所示的咔唑化合物。
然而,专利文献3仅揭示有具有以咔唑的4位与咔唑的4位键结而成的骨架的双咔唑化合物等。
专利文献4中,作为有机EL元件的主体材料揭示有如下所示的咔唑化合物。
然而,专利文献4仅揭示有具有以咔唑的4位与茀的4位键结而成的骨架的化合物等。
专利文献5、专利文献6、专利文献7中,作为有机EL元件的主体材料揭示有如下所示的咔唑化合物。
然而,该些专利文献并未揭示出使用同一分子内具有两个以上以咔唑的4位与二苯并呋喃或二苯并噻吩的1位键结而成的骨架的化合物的有机EL元件的有用性。
发明内容
为了将有机EL元件应用于平板显示器(flat panel display)等的显示元件,而必须在改善元件的发光效率的同时充分确保驱动时的稳定性。本发明是鉴于上述现状,目的在于提供一种具有高效率且高驱动稳定性的实用上有用的有机EL元件及适宜于该有机EL元件的化合物。
本发明人等人进行努力研究,结果发现藉由将同一分子内具有两个以上以咔唑(carbazole)的4位与二苯并呋喃(dibenzofuran)或二苯并噻吩(dibenzothiophene)的1位键结而成的骨架的化合物用于有机EL元件而显示出优异的特性,从而完成了本发明。
本发明是有关于一种有机电场发光元件,其是在基板上积层阳极、有机层及阴极而成的有机电场发光元件,其特征在于:在选自由发光层、空穴传输层、电子传输层、空穴阻挡层、电子阻挡层及激子阻挡层所组成的组群中的至少一个层中含有通式(1)所表示的咔唑化合物。
式中,A为n价的碳数6~30的芳香族烃基、碳数3~30的芳香族杂环基、或2个~6个该些芳香族烃基、芳香族杂环基连结而成的芳香族基,n为2或3的整数。该芳香族烃基或该芳香族杂环基具有取代基的情况下的取代基分别独立地表示碳数1~10的烷基、碳数3~10的环烷基、碳数1~10的烷氧基、-OAr、-N(Ar)2、-Si(Ar)3。R分别独立地为氢、碳数1~10的烷基、碳数3~10的环烷基、碳数1~10的烷氧基、-OAr、-N(Ar)2、-Si(Ar)3、碳数6~10的芳香族烃基、碳数3~10的芳香族杂环基或2个~3个该些芳香族烃基、芳香族杂环基连结而成的芳香族基。Ar为碳数6~10的芳香族烃基、碳数3~10的芳香族杂环基或2个~3个该些芳香族烃基、芳香族杂环基连结而成的芳香族基,多个Ar可相同也可不同。X分别独立地表示氧或硫。另外,上述芳香族烃基、芳香族杂环基也可具有取代基。
通式(1)中,R较佳为氢。另外,通式(1)中,A可为下述式(2)~下述式(5)中任一个所表示的n价的芳香族基。
式(2)~式(5)中,Y分别独立地表示C、C(R)或氮,n个Y为C。其中,式(4)中的Y的n+1个为碳(C)。n及R与通式(1)含义相同。n个C具有用以提供n价基团的结合键。进而,式(4)的中央的环上所存在的一个Y具有与邻接环键结的C。
含有上述通式(1)所表示的咔唑化合物的层可为含有磷光发光掺杂剂(phosphorescentluminescence dopant)的发光层。
发明的效果
本发明的有机EL元件中所使用的通式(1)所表示的咔唑化合物在同一分子内具有两个以上以咔唑的4位与二苯并呋喃或二苯并噻吩的1位键结的骨架,藉此与在其他取代位置咔唑与二苯并呋喃或二苯并噻吩键结的情况或即便取代位置相同但同一分子内仅具有一个骨架的情况相比,可维持更高的空穴传输性并且提高电子传输性。进而,该咔唑化合物具有平衡性良好且优异的两电荷的注入传输特性,因此可认为在将该化合物作为磷光主体材料而用于有机EL元件的情况下,发光层中的电荷的平衡性变得良好,因此空穴与电子的再结合机率变高,本发明的有机EL元件可达成高发光效率。
在将该咔唑化合物用作空穴传输层或电子阻挡层的材料的情况下,由于其良好的空穴注入传输特性,故而会带来元件的驱动电压的降低、以及发光效率的提高。
另外,该咔唑化合物对封闭掺杂剂的最低三重态激发状态的能量而言具有充分高的最低三重态激发状态的能量,因此若用作激子阻挡层的材料,则可有效抑制自掺杂剂向邻接的含有该化合物的层的三重态激发能量的转移,可获得高发光效率。
此外,该咔唑化合物在同一分子内具有两个以上以咔唑的4位与二苯并呋喃或二苯并噻吩的1位键结的骨架,藉此与在同一分子内仅具有一个骨架的情况相比,玻璃转移温度(glasstransition temperature)变高,显示出更高的热稳定性与良好的非晶质(amorphous)特性,另外,电化学性稳定,故而可实现长驱动寿命,高耐久性的有机EL元件。
本发明的有机EL元件就发光特性、驱动寿命以及耐久性而言为能满足实用的水准(level),在对平板显示器(移动电话显示元件、车载显示元件、办公自动化电脑(Office Automationcomputer,OA computer)显示元件或电视(television)等)、发挥出作为面发光体的特征的光源(照明、影印机的光源、液晶显示器或计量仪器类的背光(back light)光源)、显示板或信标灯(beacon light)等的应用中其技术价值很大。
附图说明
图1是表示有机EL元件的构造例的剖面图。
图2表示咔唑化合物(23)的1H-NMR图表。
具体实施方式
本发明的有机EL元件在有机层中含有上述通式(1)所表示的咔唑化合物。
在上述通式(1)中,A为n价的碳数6~30的芳香族烃基、碳数3~30的芳香族杂环基或2个~6个该些芳香族烃基或芳香族杂环基连结而成的芳香族基。较佳为碳数6~10的芳香族烃基、碳数3~10的芳香族杂环基或2个~6个该些芳香族烃基或芳香族杂环基连结而成的芳香族基。在芳香族杂环基的情况下,构成芳香族杂环的杂原子(hetero-atom)较佳为氧、硫、氮或硅等,更佳为氮。杂原子的个数较佳为1个~3个。芳香族烃基及芳香族杂环基可为单环也可为缩合环,但较佳为单环或2环~3环的缩合环,更佳为单环或2环的缩合环。n为2或3的整数。
上述芳香族烃基及芳香族杂环基可为未经取代的芳香族烃基或芳香族杂环基,也可为经取代的芳香族烃基或芳香族杂环基。在为芳香族烃基或芳香族杂环基连结而成的芳香族基的情况下,该芳香族基中所含的芳香族烃基或芳香族杂环基可相同也可不同,也可包含芳香族烃基与芳香族杂环基两个。
未经取代的芳香族烃基及芳香族杂环基的具体例可列举:自苯、并环戊二烯(pentalene)、茚、萘、薁、庚搭烯(heptalene)、艾氏剂(octalene)、苯并二茚、苊、茀、葩(phenalene)、菲、蒽、三茚(trindene)、萤蒽(fluoranthene)、醋菲烯(acephenanthrylene)、醋蒽烯(aceanthrylene)、三亚苯(triphenylene)、芘(pyrene)、屈(chrysene)、苯并蒽(tetraphene)、并四苯(tetracene)、七曜烯(pleiadene)、苉(picene)、苝(perylene)、戊芬(pentaphene)、并五苯(pentacene)、四伸苯(tetraphenylene)、胆蒽(cholanthrylene)、六螺烯(hexahelicene)、己芬(hexaphene)、并六苯(hexacene)、玉红省(rubicene)、蔻(coronene)、联伸三萘(trinaphthylene)、庚芬(heptaphene)、并七苯(heptacene)、吡蒽(pyranthrene)、呋喃、吡喃、噻吩、噻喃、吡咯、咪唑、吡唑、恶唑、异恶唑、噻唑、异噻唑、硒唑(selenazole)、碲唑(tellurazole)、吡啶、吡嗪、嘧啶、哒嗪、三嗪、噻咯(silole)、苯并呋喃、异苯并呋喃、异苯并吡喃(isochromene)、苯并吡喃(chromene)、二苯并呋喃、氧杂蒽(xanthene)、二苯并对二恶英(oxanthrene)、迫二苯并吡喃并二苯并吡喃(peri-Xanthenoxanthene)、硫茚(thianaphthene)、异硫茚、异硫苯并吡喃、硫苯并吡喃、萘并噻吩、二苯并噻吩、噻吨、噻蒽(thianthrene)、吩恶噻(phenoxathiin)、吲哚嗪(indolizine)、吲哚、异吲哚、苯并咪唑、吲唑、嘌呤、苯并恶唑、苯并异恶唑、苯并噻唑、苯并异噻唑、喹嗪(quinazine)、喹啉、异喹啉、萘啶(naphthyridine)、酞嗪(phthalazine)、喹恶啉、喹唑啉、噌啉(cinnoline)、喋啶、咔唑、咔啉(carboline)、啡啶、吖啶、呸啶(perimidine)、啡啉、吩嗪(phenazine)、吩恶嗪、吩噻嗪、吩硒嗪(phenoselenazine)、吩碲嗪(phenotellurazine)、奥沙拉嗪(anthyridine)、硅茚、硅茀、硅蒽、硅蒽烯(silanthrene)、吩恶硅(phenoxasilin)、吩噻硅(phenothiasilin)、或环戊基硼酸(phenazasiline)等中去除n个氢所生成的n价基团,较佳为自苯、萘、呋喃、噻吩、吡咯、咪唑、吡唑、恶唑、异恶唑、噻唑、异噻唑、吡啶、吡嗪、嘧啶、哒嗪、三嗪、噻咯、苯并呋喃、异苯并呋喃、硫茚、异硫茚、吲哚、异吲哚、苯并咪唑、吲唑、苯并恶唑、苯并异恶唑、苯并噻唑、苯并异噻唑、喹啉、异喹啉、萘啶、酞嗪、喹恶啉、喹唑啉、噌啉、硅茚中去除n个氢所生成的n价基团。
在为多个未经取代的芳香族烃基或芳香族杂环基连结而成的芳香族基(以下,称为连结芳香族基)的情况下,构成该连结芳香族基的未经取代的芳香族烃基或芳香族杂环基适宜为上述的芳香族烃基、芳香族杂环基或两个。在该情况下,由于连结芳香族基整体成为n价基团,故而有构成该连结芳香族基的未经取代的芳香族烃基或芳香族杂环基的价数与上述不同的情况。另外,连结芳香族基中含有通式(1)中所显示的二苯并呋喃环或二苯并噻吩环(将两个称为DBFT环)与咔唑环直接键结而成的结构并不理想。
连结芳香族基中,连结的个数较佳为2~4,更佳为2~3,连结的芳香环可相同也可不同。在该情况下,式(1)中,与咔唑的氮键结的键结位置并无限定,可为连结而成的芳香族环的末端部的环,也可为中央部的环。此处,芳香族环为统称芳香族烃基及芳香族杂基的含义。
此处,由2个~6个芳香族环连结而成的芳香族化合物所生成的2价连结芳香族基的情况例如以下述式表示。
(式(15)~式(17)中,Ar1~Ar6表示经取代或未经取代的芳香族环)
在为连结芳香族基的情况下,该连结芳香族基可未经取代,也可具有取代基。由2个~6个芳香族环连结而成的芳香族化合物所生成的n价的未经取代的连结芳香族基的具体例可列举:自联苯、苯基吡啶、苯基嘧啶、苯基三嗪、联吡啶、联嘧啶、联三嗪、联三苯(terphenyl)、二苯基吡啶、二苯基嘧啶、二苯基三嗪、双三嗪基苯(bistriazinylbenzene)、三联吡啶、苯基联三苯、苯基萘、苯基喹啉、联萘、联喹啉、二苯基萘、二苯基喹啉、苯基二苯并呋喃、苯基二苯并噻吩、苯基咔唑、二苯并呋喃基吡啶、二苯并噻吩基吡啶、吡啶基咔唑、二苯并呋喃基咔唑、二苯并噻吩基咔唑、咔唑基咔唑、二苯基咔唑、咔唑基联苯、咔唑基联三苯、双咔唑基苯或双咔唑基联苯等中去除n个氢所生成的n价基团,较佳为自联苯、苯基吡啶、苯基嘧啶、苯基三嗪、联吡啶、联嘧啶、联三嗪、联三苯、二苯基吡啶、二苯基嘧啶、二苯基三嗪、双三嗪基苯、三联吡啶、苯基萘或苯基喹啉中去除n个氢所生成的n价基团。
上述芳香族烃基或芳香族杂环基也可具有取代基,在具有取代基的情况下,取代基的总数为1~6。较佳为1~4,更佳为1~2。另外,在上述芳香族烃基或芳香族杂环基具有两个以上取代基的情况下,该等取代基可相同也可不同。在连结芳香族基具有取代基的情况下,与构成连结芳香族基的芳香族烃基或芳香族杂环基的取代基相同。
在上述芳香族烃基或芳香族杂环基具有取代基的情况下,取代基分别独立地为碳数1~10的烷基、碳数3~10的环烷基、碳数1~10的烷氧基、-OAr、-N(Ar)2、-Si(Ar)3。Ar为碳数6~10的芳香族烃基、碳数3~10的芳香族杂环基或2个~3个该些芳香族烃基、芳香族杂环基连结而成的连结芳香族基,多个Ar可相同也可不同。另外,在Ar为芳香族烃基、芳香族杂环基或连结芳香族基的情况下,该些基团可具有取代基,但限定在上述碳数的范围内。该取代基是自上述中选择,但较佳为碳数1~6的烷基、或碳数1~6的烷氧基。
烷基的具体例可列举:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基或癸基等,较佳为甲基、乙基、丙基、丁基、戊基、己基、庚基或辛基。更佳为甲基、乙基、丙基、丁基、戊基或己基等碳数1~6的烷基。上述烷基可为直链也可分支。
环烷基的具体例可列举:环丙基、环丁基、环戊基、环己基、甲基环己基、环庚基、环辛基、环壬基或环癸基等,较佳为环戊基、环己基或甲基环己基等碳数3~8的环烷基。
烷氧基的具体例可列举:甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基或癸氧基等,较佳为甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基或辛氧基。更佳为甲氧基、乙氧基、丙氧基、丁氧基、戊氧基或己氧基等碳数1~6的烷氧基。上述烷氧基可为直链也可分支。
通式(1)中,较佳的A可列举上述式(2)~上述式(5)、较佳为式(2)、式(3)或式(4)所表示的n价基团。式(2)~式(5)中,Y分别独立地表示C、C(R)或氮,n个Y为C。其中,式(4)中的Y的n+1个为C。构成各六员环的Y中,较佳为0个~3个Y为氮。提供n价基团的n个C可存在于同一个环上,也可存在于不同的环上。此处,n及R具有与通式(1)的n及R相同的含义。
在通式(1)及Y为C(R)的情况下,R分别独立地为氢、碳数1~10的烷基、碳数3~10的环烷基、碳数1~10的烷氧基、-OAr、-N(Ar)2、-Si(Ar)3、碳数6~10的芳香族烃基、碳数3~10的芳香族杂环基或2个~3个该些芳香族烃基、芳香族杂环基连结而成的连结芳香族基。较佳为氢、碳数1~6的烷基、碳数3~8的环烷基、碳数1~6的烷氧基、碳数6~10的芳香族烃基、碳数3~10的芳香族杂环基或2个~3个该些芳香族烃基、芳香族杂环基连结而成的连结芳香族基。
此处,-OAr、-N(Ar)2、-Si(Ar)3中的Ar与通式(1)的A的说明中作为芳香族烃基或芳香族杂环基具有取代基的情况下的取代基所说明的-OAr、-N(Ar)2、-Si(Ar)3中的Ar具有相同的含义。另外,关于芳香族烃基、芳香族杂环基或连结芳香族基,除碳数的范围不同以外,与通式(1)的A相同。烷基、环烷基、烷氧基的具体例与通式(1)的A的说明中作为芳香族烃基或芳香族杂环基具有取代基的情况下的取代基所说明的该些烷基、环烷基、烷氧基相同。
通式(1)及式(2)~式(5)中,分别相同的符号及式只要无特别说明,则可理解为具有相同的含义。
通式(1)中,X分别独立地表示氧或硫。
本发明的有机EL元件中所使用的咔唑化合物可以4位经卤素原子取代的咔唑衍生物与1位经卤素原子取代的二苯并呋喃衍生物或二苯并噻吩衍生物作为起始原料,由具有以咔唑的4位与二苯并呋喃或二苯并噻吩的1位键结而成的骨架的DBFT-咔唑化合物,根据目标化合物的结构而选择原料,藉此使用公知的方法合成。
例如,具有以咔唑的4位与二苯并噻吩(DBT)(dibenzothiophene)的1位键结而成的骨架的DBT-咔唑化合物可以有机化学杂志(The Joumal of Organic Chemistry)1995,60,7508-7510.中所示的合成例作为参考使1-溴二苯并噻吩的溴原子转化为硼酸频哪醇酯(boronicacid pinaeol ester)之后,藉由与4-溴咔唑的铃木-宫浦交叉偶合反应(Suzuki-Miyaura crosscoupling reaction)而合成。
藉由将该DBT-咔唑化合物的氮上的氢原子藉由例如乌尔曼反应(Ullmann reaction)等交叉偶合反应而取代为对应的芳香族基,可合成通式(1)所表示的咔唑化合物。
将通式(1)所表示的咔唑化合物的具体例示于以下,但并不限定于该些化合物。
上述通式(1)所表示的咔唑化合物藉由包含于在基板上积层阳极、多个有机层及阴极而成的有机EL元件的至少一个有机层中而提供优异的有机EL元件。有机层较佳为至少具有发光层,此外也较佳为具有空穴传输层、电子传输层、空穴阻挡层、电子阻挡层或激子阻挡层。含有通式(1)所表示的咔唑化合物的有机层适宜为发光层、空穴传输层、电子传输层、空穴阻挡层、电子阻挡层或激子阻挡层。更佳为以含有磷光发光掺杂剂的发光层的主体材料的形式含有。
本发明的有机EL元件在积层于基板上的阳极与阴极之间具有包含至少一个发光层的有机层,且至少一个有机层含有上述通式(1)所表示的咔唑化合物。有利的是使通式(1)所表示的咔唑化合物与磷光发光掺杂剂一并含有在发光层中。
其次,一面参照附图一面对本发明的有机EL元件的构造进行说明,但本发明的有机EL元件的构造并不受图示构造的任何限定。
图1是表示通常的有机EL元件的构造例的剖面图,1表示基板,2表示阳极,3表示空穴注入层,4表示空穴传输层,5表示发光层,6表示电子传输层,7表示阴极。本发明的有机EL元件也可与发光层邻接而具有激子阻挡层,另外,也可在发光层与空穴注入层之间具有电子阻挡层。激子阻挡层可插入至发光层的阳极侧、阴极侧的任一侧,也可同时插入至两侧。本发明的有机EL元件中,具有基板、阳极、发光层及阴极作为必需的层,但较佳为具有空穴注入传输层、电子注入传输层作为必需的层以外的层,较佳为进而在发光层与电子注入传输层之间具有空穴阻挡层。此外,空穴注入传输层意指空穴注入层与空穴传输层的任一个或两个,电子注入传输层意指电子注入层与电子传输层的任一个或两个。
此外,也可为与图1相反的构造,即在基板1上依序积层阴极7、电子传输层6、发光层5、空穴传输层4、阳极2,在该情况下,也可视需要追加层或省略层。
-基板-
本发明的有机EL元件较佳为由基板支撑。关于该基板,并无特别限制,只要为现有以来惯用于有机EL元件中的基板即可,例如可使用包含玻璃、透明塑胶、石英等的基板。
-阳极-
有机EL元件中的阳极可较佳地使用以功函数大(4eV以上)的金属、合金、导电性化合物及该些的混合物作为电极物质的阳极。此种电极物质的具体例可列举:Au等金属、CuI、氧化铟锡(ITO)、SnO2、ZnO等导电性透明材料。另外,也可使用IDIXO(In2O3-ZnO)等可以非晶质制作透明导电膜的材料。阳极可使该些电极物质藉由蒸镀或溅镀(sputtefing)等方法而形成薄膜,利用光微影法(photolithography method)形成所需的形状的图案(pattern),或者在并未严格要求图案精度的情况(100μm以上左右)下,也可在上述电极物质的蒸镀或溅镀时经由所需的形状的遮罩(mask)形成图案。或者,在使用如有机导电性化合物般可涂布的物质的情况下,也可使用印刷方式、涂布(coating)方式等湿式成膜法。在自该阳极取出发光的情况下,理想的是使透射率大于10%,另外,作为阳极的薄片电阻(sheet resistance)较佳为数百Ω/□以下。进而膜厚虽也取决于材料,但通常在10nm~1000nm、较佳为10nm~200nm的范围内选择。
-阴极-
另一方面,阴极可使用以功函数小(4eV以下)的金属(称为电子注入性金属)、合金、导电性化合物及该些的混合物作为电极物质的阴极。此种电极物质的具体例可列举:钠、钠-钾合金、镁、锂、镁/铜混合物、镁/银混合物、镁/铝混合物、镁/铟混合物、铝/氧化铝(Al2O3)混合物、铟、锂/铝混合物、稀土类金属等。该些之中,就电子注入性及对氧化等的耐久性的方面而言,较佳为电子注入性金属与作为功函数的值大于电子注入性金属而稳定的金属的第二金属的混合物、例如镁/银混合物、镁/铝混合物、镁/铟混合物、铝/氧化铝(Al2O3)混合物、锂/铝混合物、铝等。阴极可藉由使该些电极物质利用蒸镀或溅镀等方法形成薄膜而制作。另外,作为阴极的薄片电阻较佳为数百Ω/□以下,膜厚通常在10nm~5μm、较佳为50nm~200nm的范围内选择。此外,为了使所发出的光透过,只要有机EL元件的阳极或阴极的任一个为透明或半透明,则会使发光亮度提高而为较佳情况。
另外,在阴极上以1nm~20nm的膜厚制作上述金属后,在其上制作在阳极的说明中所列举的导电性透明材料,藉此可制作透明或半透明的阴极,藉由应用该阴极可制作阳极与阴极两个具有透射性的元件。
-发光层-
发光层可为萤光发光层、磷光发光层的任一个,较佳为磷光发光层。
在发光层为萤光发光层的情况下,萤光发光材料可单独使用至少一种萤光发光材料,但较佳为使用萤光发光材料作为萤光发光掺杂剂并含有主体材料。
发光层中的萤光发光材料可使用通式(1)所表示的咔唑化合物,但由于由多个专利文献等所知而也可自该等如下化合物中选择。例如可列举:以苯并恶唑衍生物、苯并噻唑衍生物、苯并咪唑衍生物、苯乙烯基苯衍生物、聚苯基衍生物、二苯基丁二烯衍生物、四苯基丁二烯衍生物、萘二甲酰亚胺衍生物、香豆素衍生物、缩合芳香族化合物、哌瑞酮(perinone)衍生物、恶二唑衍生物、恶嗪衍生物、醛连氮(aldazine)衍生物、吡嗪(pyrazine)衍生物、环戊二烯衍生物、双苯乙烯基蒽衍生物、喹吖啶酮衍生物、吡咯并吡啶衍生物、噻二唑并吡啶衍生物、苯乙烯基胺衍生物、二酮基吡咯并吡咯衍生物、芳香族二次甲基化合物、8-羟基喹啉(quinolinol)衍生物的金属错合物或吡咯亚甲基(pyrromethene)衍生物的金属错合物、稀土类错合物、过渡金属错合物为代表的各种金属错合物等,聚噻吩、聚苯、聚苯乙炔等聚合物化合物,有机硅烷衍生物等。可较佳地列举缩合芳香族化合物、苯乙烯基化合物、二酮基吡咯并吡咯化合物、恶嗪化合物、吡咯亚甲基金属错合物、过渡金属错合物、镧系错合物,可更佳地列举并四苯、芘、屈、三亚苯、苯并[c]菲、苯并[a]蒽、并五苯、苝、萤蒽、苊并萤蒽、二苯并[a,j]蒽、二苯并[a,h]蒽、苯并[a]并四苯、并六苯、蒽嵌蒽(anthanthrene)、萘并[2,1-f]异喹啉、α-萘啡啶(α-naphthaphenanthridine)、菲并恶唑、喹啉并[6,5-f]喹啉、苯并萘并噻吩(benzothiophanthrene)等。该些也可具有烷基、芳基、芳香族杂环基、二芳基胺基作为取代基。
在使用上述萤光发光材料作为萤光发光掺杂剂并含有主体材料的情况下,萤光发光掺杂剂在发光层中的含量较佳为在0.01重量%~20重量%、较佳为0.1重量%~10重量%的范围内。
通常,有机EL元件是自阳极、阴极的两电极将电荷注入至发光物质,生成激发状态的发光物质而使之发光。在电荷注入型的有机EL元件的情况下,所生成的激子中,激发为单态激发状态的激子为25%,其余75%被激发为三重态激发状态。如“先进材料(Advanced Materials)”2009,21,4802-4806.所示,己知特定的萤光发光物质藉由系间交差(intersystem crossing)等使能量转化为三重态激发状态后,藉由三重态-三重态消减或热能的吸收而逆系间交差(inverseintersystem crossing)成单态激发状态从而放射萤光,表现出热活性化延迟萤光。本发明的有机EL元件也可表现出延迟萤光。在该情况下,也可包含萤光发光及延迟萤光发光两个。但是,也可为发光的一部分或部分地源自主体材料的发光。
在发光层为延迟萤光发光层的情况下,发光层中也可单独使用延迟萤光材料,但较佳为使用延迟萤光材料作为延迟萤光发光掺杂剂并混合主体材料。
发光层中的延迟萤光发光材料可使用本发明化合物,也可自公知的延迟萤光发光材料中选择。例如可列举非专利文献“Appl.Phys.Lett.”98,083302(2011)中所记载的吲哚并咔唑衍生物或“自然(Nature)”492,234(2012)中所记载的咔唑衍生物等,但并不限定于该些化合物。
将延迟萤光材料的具体例示于下述,但并不限定于下述化合物。
在使用上述延迟萤光发光材料作为延迟萤光发光掺杂剂并含有主体材料的情况下,延迟萤光发光掺杂剂在发光层中的含量较佳为在0.01重量%~50重量%、较佳为0.1重量%~20重量%、更佳为0.01%~10%的范围内。
发光层中的延迟萤光主体材料可使用本发明化合物,但也可自本发明化合物以外的化合物中选择。例如可使用萘、蒽、菲、芘、屈、并四苯、三亚苯、苝、萤蒽、茀、茚等具有缩合芳基环的化合物或其衍生物、N,N′-二萘基-N,N′-二苯基-4,4′-二苯基-1,1′-二胺等芳香族胺衍生物、以三(8-羟基喹啉(quinolinato))铝(III)为代表的金属螯合化8-羟基喹啉酮(oxinoid)化合物、二苯乙烯基苯衍生物等双苯乙烯基衍生物、四苯基丁二烯衍生物、茚衍生物、香豆素衍生物、恶二唑衍生物、吡咯并吡啶衍生物、哌瑞酮衍生物、环戊二烯衍生物、吡咯并吡咯衍生物、噻二唑并吡啶衍生物、二苯并呋喃衍生物、咔唑衍生物、吲哚并咔唑衍生物、三嗪衍生物、聚合物系中的聚苯乙炔衍生物、聚对苯衍生物、聚茀衍生物、聚乙烯基咔唑衍生物、聚噻吩衍生物、芳基硅烷衍生物等,但并无特别限定。
在发光层为磷光发光层的情况下,含有磷光发光掺杂剂与主体材料。磷光发光掺杂剂较佳为含有包含选自钌、铑、钯、银、铼、锇、铱、铂及金中的至少一种金属的有机金属错合物。具体而言可列举以下的专利文献中所记载的化合物,但并不限定于该些化合物。
WO2009/073245A1、WO2009/046266号A1、WO2007/095118A1、WO2008/156879A1、WO2008/140657A1、US2008/261076A1、日本专利特表2008-542203号公报、WO2008/054584A1、日本专利特表2008-505925号公报、日本专利特表2007-522126号公报、日本专利特表2004-506305号公报、日本专利特表2006-513278号公报、日本专利特表2006-50596号公报、WO2006/046980A1、WO2005/113704A1、US2005/260449A1、US2005/2260448A1、US2005/214576A1、WO2005/076380A1、US2005/119485号A1、WO2004/045001A1、WO2004/045000A1、WO2006/100888A1、WO2007/004380A1、WO2007/023659A1、WO2008/035664A1、日本专利特开2003-272861号公报、日本专利特开2004-111193号公报、日本专利特开2004-319438号公报、日本专利特开2007-2080号公报、日本专利特开2007-9009号公报、日本专利特开2007-227948号公报、日本专利特开2008-91906号公报、日本专利特开2008-311607号公报、日本专利特开2009-19121号公报、日本专利特开2009-46601号公报、日本专利特开2009-114369号公报、日本专利特开2003-253128号公报、日本专利特开2003-253129号公报、日本专利特开2003-253145号公报、日本专利特开2005-38847号公报、日本专利特开2005-82598号公报、日本专利特开2005-139185号公报、日本专利特开2005-187473号公报、日本专利特开2005-220136号公报、日本专利特开2006-63080号公报、日本专利特开2006-104201号公报、日本专利特开2006-111623号公报、日本专利特开2006-213720号公报、日本专利特开2006-290891号公报、日本专利特开2006-298899号公报、日本专利特开2006-298900号公报、WO2007/018067A1、WO2007/058080A1、WO2007/058104A1、日本专利特开2006-131561号公报、日本专利特开2008-239565号公报、日本专利特开2008-266163号公报、日本专利特开2009-57367号公报、日本专利特开2002-117978号公报、日本专利特开2003-123982号公报、日本专利特开2003-133074号公报、日本专利特开2006-93542号公报、日本专利特开2006-131524号公报、日本专利特开2006-261623号公报、日本专利特开2006-303383号公报、日本专利特开2006-303394号公报、日本专利特开2006-310479号公报、日本专利特开2007-88105号公报、日本专利特开2007-258550号公报、日本专利特开2007-324309号公报、日本专利特开2008-270737号公报、日本专利特开2009-96800号公报、日本专利特开2009-161524号公报、WO2008/050733号公报、日本专利特开2003-73387号公报、日本专利特开2004-59433号公报、日本专利特开2004-155709号公报、日本专利特开2006-104132号公报、日本专利特开2008-37848号公报、日本专利特开2008-133212号公报、日本专利特开2009-57304号公报、日本专利特开2009-286716号公报、日本专利特开2010-83852号公报、日本专利特表2009-532546号公报、日本专利特表2009-536681号公报、日本专利特表2009-542026号公报等。
较佳的磷光发光掺杂剂可列举:具有Ir等贵金属元素作为中心金属的Ir(PPy)3等错合物类、Ir(bt)2(acac)等错合物类、PtOEt3等错合物类。将该些错合物类的具体例示于以下,但并不限定于下述化合物。
上述磷光发光掺杂剂在发光层中的含量较佳为在0.1重量%~50重量%的范围内。更佳为1重量%~30重量%。
发光层中的主体材料较佳为使用上述通式(1)所表示的咔唑化合物。但是,在将该咔唑化合物用于发光层以外的其他任一有机层的情况下,发光层中所使用的材料也可为通式(1)所表示的咔唑化合物以外的其他主体材料。另外,也可将通式(1)所表示的咔唑化合物与其他主体材料并用。进而,也可并用多种公知的主体材料而使用。
可使用的公知的主体材料较佳为具有空穴传输能力、电子传输能力,且防止发光的长波长化,此外且具有高玻璃转移温度的化合物。
关于此种其他主体材料,由于由多个专利文献等所知而可自下述材料中选择。主体材料的具体例并无特别限定,可列举:吲哚(indole)衍生物、咔唑衍生物、吲哚并咔唑衍生物、三唑衍生物、恶唑衍生物、恶二唑衍生物、咪唑衍生物、聚芳基烷烃衍生物、吡唑啉(pyrazoline)衍生物、吡唑啉酮衍生物、苯二胺衍生物、芳基胺衍生物、经胺基取代的查耳酮衍生物、苯乙烯基蒽衍生物、茀酮衍生物、腙衍生物、均二苯乙烯衍生物、硅氮烷衍生物、芳香族三级胺化合物、苯乙烯基胺化合物、芳香族二次甲基系化合物、卟啉系化合物、蒽醌二甲烷衍生物、蒽酮衍生物、二苯基醌(diphenyl quinone)衍生物、噻喃二氧化物衍生物、萘苝等杂环四羧酸酐、酞菁衍生物、8-羟基喹啉(quinolinol)衍生物的金属错合物或金属酞菁、苯并恶唑或苯并噻唑衍生物的金属错合物为代表的各种金属错合物,聚硅烷系化合物、聚(N-乙烯基咔唑)衍生物、苯胺系共聚物、噻吩低聚物、聚噻吩衍生物、聚苯衍生物、聚苯乙炔衍生物、聚茀衍生物等高分子化合物等。
-注入层-
注入层是指用以降低驱动电压或提高发光亮度而设置在电极与有机层间的层,有空穴注入层与电子注入层,也可存在于阳极与发光层或空穴传输层之间、及阴极与发光层或电子传输层之间。也可视需要设置注入层。
-空穴阻挡层-
空穴阻挡层广义而言是指包含具有电子传输层的功能,具有传输电子的功能并且传输空穴的能力非常小的空穴阻挡材料,可藉由传输电子并且阻挡空穴而提高空穴与电子在发光层中再结合的机率。
空穴阻挡层较佳为使用通式(1)所表示的咔唑化合物,在将该咔唑化合物用于其他任一有机层的情况下,也可使用公知的空穴阻挡材料。另外,空穴阻挡层的材料可视需要使用下述电子传输层的材料。
-电子阻挡层-
电子阻挡层是指包含具有传输空穴的功能且传输电子的能力非常小的电子阻挡材料,可藉由传输空穴且阻挡电子而提高空穴与电子在发光层中再结合的机率。
电子阻挡层的材料较佳为使用通式(1)所表示的咔唑化合物,在将该咔唑化合物用于其他任一有机层的情况下,可视需要使用下述空穴传输层的材料。电子阻挡层的膜厚较佳为3nm~100nm,更佳为5nm~30nm。
-激子阻挡层-
激子阻挡层是指用以阻挡藉由在发光层内空穴与电子再结合而产生的激子拡散至电荷传输层的层,藉由插入本层可将激子有效地封闭于发光层内,可提高元件的发光效率。激子阻挡层可邻接于发光层而插入至阳极侧、阴极侧的任一侧,也可同时插入至两侧。
激子阻挡层的材料可使用通式(1)所表示的咔唑化合物,在将该咔唑化合物用于其他任一有机层的情况下,可自之前公知的化合物中选择任意的化合物而使用。公知的激子阻挡材料例如可列举:1,3-二(9-咔唑基)苯(mCP)或双(2-甲基-8-羟基喹啉(quinolinato))-4-苯基苯酚铝(III)(BAlq)。
-空穴传输层-
空穴传输层包含具有传输空穴的功能的空穴传输材料,空穴传输层可设置单层或多层。
空穴传输材料具有空穴的注入或传输、电子的障壁性的任一种性质,可为有机物、无机物的任一种。空穴传输层中较佳为使用通式(1)所表示的咔唑化合物,但在将该咔唑化合物用于其他任一有机层的情况下,可自之前公知的化合物中选择任意的化合物而使用。可使用的公知的空穴传输材料例如可列举:咔唑衍生物、三唑衍生物、恶唑衍生物、恶二唑衍生物、咪唑衍生物、聚芳基烷烃衍生物、吡唑啉衍生物、吡唑啉酮衍生物、苯二胺衍生物、芳基胺衍生物、经胺基取代的查耳酮衍生物、苯乙烯基蒽衍生物、茀酮衍生物、腙衍生物、均二苯乙烯衍生物、硅氮烷衍生物、芳香族三级胺化合物、苯乙烯基胺化合物、卟啉化合物、聚硅烷系化合物、苯胺系共聚物,另外,也可列举导电性高分子低聚物、尤其是噻吩低聚物等,但较佳为使用卟啉化合物、芳香族三级胺化合物及苯乙烯基胺化合物,更佳为使用芳香族三级胺化合物。
-电子传输层-
所谓电子传输层,包含具有传输电子的功能的电子传输材料,可设置单层或多层电子传输层。
电子传输材料(也有兼作空穴阻挡材料的情况)只要具有将自阴极注入的电子传递至发光层的功能即可。电子传输层中较佳为使用通式(1)所表示的咔唑化合物,但在将该咔唑化合物用于其他任一有机层的情况下,可自之前公知的化合物中选择任意的化合物而使用,例如可列举:三唑衍生物、恶唑衍生物、咪唑衍生物、经硝基取代的茀衍生物、蒽醌二甲烷衍生物、蒽酮衍生物、二苯基醌衍生物、噻喃二氧化物衍生物、碳二酰亚胺衍生物、亚茀基甲烷衍生物、恶二唑衍生物等。进而,在上述恶二唑衍生物中,将恶二唑环的氧原子取代为硫原子而成的噻二唑衍生物、作为电子吸引基而为大众所知的具有喹恶啉环的喹恶啉衍生物也可用作电子传输材料。进而也可使用将该些材料导入至高分子链而成的高分子材料、或以该些材料作为高分子的主链的高分子材料。
实施例
以下,藉由实施例更详细地说明本发明,本发明当然并不限定于该些实施例,只要不超过其主旨,则可以各种形态实施。
藉由以下所示的合成路径来合成本发明中所使用的通式(1)所表示的咔唑化合物。此外,化合物编号与上述化学式上所标附的编号相对应。
合成例1
化合物(23)的合成
在氮气环境下,一面在室温下搅拌1-溴二苯并[b,d]噻吩(A)16.02g(0061mol)、双(频哪醇基(pinacolato))二硼23.20g(0.091mol)、乙酸钾17.93g(0.18mol)及二甲基亚砜400ml,一面添加[1,1′-双(二苯基瞵基)二茂铁]二氯钯(II)·二氯甲烷错合物2.49g(0.0031mol)之后,在80℃下一而加热一而搅拌4小时。将反应溶液冷却至室温后,添加蒸馏水2,400ml,利用乙酸乙酯(3×600ml)对该溶液进行萃取。利用蒸馏水400ml对有机层进行清洗,利用无水硫酸镁干燥后,将溶剂减压蒸馏去除。藉由硅胶管柱层析法(silica gel columnchromatography)对所获得的残渣进行纯化,获得硼酸频哪醇酯(B)12.09g(0.039mol,产率64%)。
大气压化学电离-飞行时间质谱(Atmospheric Pressure Chemical Ionization-Time Of FlightMass Spectrometry,APCI-TOFMS),m/z 310[M]+
在氮气环境下,一面在室温下搅拌4-溴咔唑(C)4.19g(0.017mol)、硼酸频哪醇酯(B)6.87g(0.022mol)、碳酸钠水溶液(2.0mol/l)36ml、乙醇43ml及甲苯128ml,一面添加四(三苯基膦)钯(0)0.393g(0.00034mol)之后,在70℃下一面加热回流一面搅拌19.5小时。将反应溶液冷却至室温后,添加蒸馏水40ml。将该溶液浓缩后,利用二氯甲烷(3×150ml)进行萃取。利用无水硫酸镁将有机层干燥后,将溶剂减压蒸馏去除。藉由硅胶管柱层析法对所获得的残渣进行纯化,以白色固体的形式获得4-(1-二苯并[b,d]噻吩基)咔唑(D)5.55g(0.016mol,产率93%)。
APCI-TOFMS,m/z 349[M]+
在氮气环境下,一面在室温下搅拌1,3-二碘苯2.33g(0.007l mol)、4-(1-二苯并[b,d]噻吩基)咔唑(D)5.43g(0.016mol)、碘化铜(I)0.142g(0.00071mol)、磷酸三钾6.00g(0.028mol)及脱水1,4-二恶烷140ml,一面添加反式-1,2-环己二胺0.85ml(0.007l mol)之后,在100℃下一面加热回流一面搅拌16小时。将反应溶液冷却至室温后,将无机盐过滤分离,将溶剂减压蒸馏去除。利用硅胶管柱层析法将所获得的残渣纯化。进而,藉由加热再打浆进行纯化,以白色固体的形式获得化合物(23)5.36g(0.0069mol,产率98%)。
将化合物(23)的质子核磁共振(Proton Nuclear Magnetic Resonance,1H-NMR)(400MHz,THF-d8)测定结果示于图2。
APCI-TOFMS,m/z 773[M+H]+
实施例l
在形成有包含膜厚110nm的氧化铟锡(ITO)的阳极的玻璃基板上利用真空蒸镀法在真空度2.0×10-5Pa下积层各薄膜。首先,在ITO上使铜酞菁(CuPC)形成为25nm的厚度作为空穴注入层。其次,使4,4′-双[N-(1-萘基)-N-苯基胺基]联苯(NPD)形成为90nm的厚度作为空穴传输层。其次,在空穴传输层上对作为发光层的主体材料的化合物(23)与作为蓝色磷光发光材料的吡啶甲酸双[2-(4,6-二氟苯基)吡啶根基-N,C2′]铱(FIrpic)自不同的蒸镀源进行共蒸镀,而使发光层形成为30nm的厚度。此时,FIrpic的浓度为10wt%。其次,使三(8-羟基喹啉)铝(Alq3)形成为30nm的厚度作为电子传输层。进而,在电子传输层上使氟化锂(LiF)形成为1nm的厚度作为电子注入层。最后,在电子注入层上使铝(Al)形成为70nm的厚度作为电极,从而制成有机EL元件。
将外部电源连接于所获得的有机EL元件并施加直流电压,结果确认到具有如表1所示的发光特性。表1中,亮度、电压及发光效率是表示以2.5mA/cm2驱动时的值。此外,可知元件发光光谱(emission spectrum)的极大波长为475nm,可获得源自FIrpic的发光。
实施例2~3
使用化合物(48)或化合物(53)代替化合物(23)作为实施例1中的发光层的主体材料,除此以外,以与实施例1相同的方式制成有机EL元件。确定为各元件发光光谱的极大波长为475nm,可获得源自Flrpic的发光。表1中表示各自的发光特性。
比较例1
使用1,3-二(9-咔唑基)苯(mCP)作为实施例1中的发光层的主体材料,除此以外,以与实施例1相同的方式制成有机EL元件。确定为元件发光光谱的极大波长为475nm,可获得源自FIrpic的发光。表1中表示发光特性。
比较例2~3
使用化合物(H1)或化合物(H2)作为实施例1中的发光层的主体材料,除此以外,以与实施例1相同的方式制成有机EL元件。确定为元件发光光谱的极大波长为475nm,可获得源自FIrpic的发光。表1中表示发光特性。
表1
实施例4
在形成有包含膜厚110nm的氧化铟锡(ITO)的阳极的玻璃基板上利用真空蒸镀法在真空度2.0×10-5Pa下积层各薄膜。首先,在ITO上使铜酞菁(CuPC)形成为25nm的厚度作为空穴注入层。其次,使4,4′-双[N-(1-萘基)-N-苯基胺基]联苯(NPD)形成为40nm的厚度作为空穴传输层。其次,在空穴传输层上对作为发光层的主体材料的化合物(23)与作为绿色磷光发光材料的三(2-苯基吡啶)铱(Ir(ppy)3)自不同的蒸镀源进行共蒸镀,使发光层形成为40nm的厚度。此时,Ir(ppy)3的浓度为10wt%。其次,使三(8-羟基喹啉)铝(Alq3)形成为20nm的厚度作为电子传输层。进而,在电子传输层上使氟化锂(LiF)形成为1nm的厚度作为电子注入层。最后,在电子注入层上使铝(Al)形成为70nm的厚度作为电极,从而制成有机EL元件。
将外部电源连接于所获得的有机EL元件并施加直流电压,结果确认到具有如表2所示的发光特性。表2中,亮度、电压及发光效率是表示以20mA/cm2驱动时的值。此外,可知元件发光光谱的极大波长为530nm,可获得源自Ir(ppy)3的发光。
实施例5~8
使用化合物(48)、化合物(50)、化合物(51)或化合物(53)代替化合物(23)作为实施例4中的发光层的主体材料,除此以外,以与实施例4相同的方式制成有机EL元件。确定为各元件发光光谱的极大波长为530nm,可获得源自Ir(ppy)3的发光。表2中表示各自的发光特性。
比较例4
使用4,4′-二(9-咔唑基)联苯(CBP)作为实施例4中的发光层的主体材料,除此以外,以与实施例4相同的方式制成有机EL元件。确定为元件发光光谱的极大波长为530nm,可获得源自Ir(ppy)3的发光。表2中表示发光特性。
比较例5~6
使用化合物(H1)或化合物(H2)作为实施例4中的发光层的主体材料,除此以外,以与实施例4相同的方式制成有机EL元件。确定为元件发光光谱的极大波长为530nm,可获得源自Ir(ppy)3的发光。表2中表示发光特性。
表2
Claims (4)
1.一种有机电场发光元件,其是在基板上积层阳极、有机层及阴极而成的有机电场发光元件,其特征在于:在选自由发光层、空穴传输层、电子传输层、空穴阻挡层、电子阻挡层及激子阻挡层所组成的组群中的至少一个层中含有通式(1)所表示的咔唑化合物,
此处,A为n价的碳数6~30的芳香族烃基、碳数3~30的芳香族杂环基、或2个~6个该些芳香族烃基、芳香族杂环基连结而成的芳香族基,n为2或3的整数,该芳香族烃基或该芳香族杂环基具有取代基的情况下的取代基分别独立地为碳数1~10的烷基、碳数3~10的环烷基、碳数1~10的烷氧基、-OAr、-N(Ar)2、或-Si(Ar)3;
R分别独立地为氢、碳数1~10的烷基、碳数3~10的环烷基、碳数1~10的烷氧基、-OAr、-N(Ar)2、-Si(Ar)3、碳数6~10的芳香族烃基、碳数3~10的芳香族杂环基或2个~3个该些芳香族烃基、芳香族杂环基连结而成的芳香族基,Ar分别独立地为碳数6~10的芳香族烃基、碳数3~10的芳香族杂环基或2个~3个该些芳香族烃基、芳香族杂环基连结而成的芳香族基;
X分别独立地为氧或硫。
2.根据权利要求1所述的有机电场发光元件,其中R为氢。
3.根据权利要求1所述的有机电场发光元件,其中A为下述式(2)~下述式(5)中任一个所表示的n价的芳香族基,
式(2)~式(5)中,Y分别独立地表示C、C(R)或氮,n个Y为C;其中,式(4)中的Y的n+1个为C;n及R与通式(1)含义相同。
4.根据权利要求1至3中任一项所述的有机电场发光元件,其中含有通式(1)所表示的咔唑化合物的层为含有磷光发光掺杂剂的发光层。
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TW201406756A (zh) | 2014-02-16 |
KR20150036600A (ko) | 2015-04-07 |
CN104471734B (zh) | 2016-11-09 |
US20150214495A1 (en) | 2015-07-30 |
EP2876699B1 (en) | 2018-02-14 |
TWI567069B (zh) | 2017-01-21 |
KR102099661B1 (ko) | 2020-04-10 |
EP2876699A1 (en) | 2015-05-27 |
US9614166B2 (en) | 2017-04-04 |
WO2014013936A1 (ja) | 2014-01-23 |
JP6169078B2 (ja) | 2017-07-26 |
EP2876699A4 (en) | 2015-12-23 |
JPWO2014013936A1 (ja) | 2016-06-30 |
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