CN113248529A - 含硼化合物及有机el元件 - Google Patents
含硼化合物及有机el元件 Download PDFInfo
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- CN113248529A CN113248529A CN202110184048.2A CN202110184048A CN113248529A CN 113248529 A CN113248529 A CN 113248529A CN 202110184048 A CN202110184048 A CN 202110184048A CN 113248529 A CN113248529 A CN 113248529A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 38
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 35
- 125000004429 atom Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 11
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 150000001454 anthracenes Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 abstract description 30
- 239000010410 layer Substances 0.000 description 114
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- 230000004888 barrier function Effects 0.000 description 22
- 238000007740 vapor deposition Methods 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 14
- -1 polycyclic aromatic compounds Chemical class 0.000 description 14
- 239000000758 substrate Substances 0.000 description 10
- 150000001639 boron compounds Chemical class 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 8
- 230000005281 excited state Effects 0.000 description 8
- 229910052750 molybdenum Inorganic materials 0.000 description 8
- 239000011733 molybdenum Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- 238000001704 evaporation Methods 0.000 description 4
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- 125000001624 naphthyl group Chemical group 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IRPWVEBIMPXCAZ-UHFFFAOYSA-N 1,3-dibromo-2-chlorobenzene Chemical compound ClC1=C(Br)C=CC=C1Br IRPWVEBIMPXCAZ-UHFFFAOYSA-N 0.000 description 2
- 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
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229940126062 Compound A Drugs 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
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- 150000003613 toluenes Chemical class 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- IWJQIFGFIYVQLJ-UHFFFAOYSA-N 1-bromo-3-(3-bromophenyl)-2-phenylbenzene Chemical group BrC1=CC=CC(C=2C(=C(Br)C=CC=2)C=2C=CC=CC=2)=C1 IWJQIFGFIYVQLJ-UHFFFAOYSA-N 0.000 description 1
- FQJQNLKWTRGIEB-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-5-[3-[5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=C(C=CC=2)C=2OC(=NN=2)C=2C=CC(=CC=2)C(C)(C)C)O1 FQJQNLKWTRGIEB-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- VQYDFPFSXHGHOD-UHFFFAOYSA-N 2-[4-(1,10-phenanthrolin-2-yl)phenyl]-1,10-phenanthroline Chemical compound C1=CN=C2C3=NC(C4=CC=C(C=C4)C4=CC=C5C=CC=6C(C5=N4)=NC=CC=6)=CC=C3C=CC2=C1 VQYDFPFSXHGHOD-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 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
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- XIVCFIYEIZBYMX-UHFFFAOYSA-N 4,6-bis(3,5-dipyridin-3-ylphenyl)-2-methylpyrimidine Chemical compound N=1C(C)=NC(C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=NC=CC=2)=CC=1C(C=1)=CC(C=2C=NC=CC=2)=CC=1C1=CC=CN=C1 XIVCFIYEIZBYMX-UHFFFAOYSA-N 0.000 description 1
- RXVALUXWPWFEMQ-UHFFFAOYSA-N 4,6-bis(3,5-dipyridin-4-ylphenyl)-2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC(C=2C=C(C=C(C=2)C=2C=CN=CC=2)C=2C=CN=CC=2)=CC(C=2C=C(C=C(C=2)C=2C=CN=CC=2)C=2C=CN=CC=2)=N1 RXVALUXWPWFEMQ-UHFFFAOYSA-N 0.000 description 1
- YOZHUJDVYMRYDM-UHFFFAOYSA-N 4-(4-anilinophenyl)-3-naphthalen-1-yl-n-phenylaniline Chemical compound C=1C=C(C=2C(=CC(NC=3C=CC=CC=3)=CC=2)C=2C3=CC=CC=C3C=CC=2)C=CC=1NC1=CC=CC=C1 YOZHUJDVYMRYDM-UHFFFAOYSA-N 0.000 description 1
- MBPCKEZNJVJYTC-UHFFFAOYSA-N 4-[4-(n-phenylanilino)phenyl]aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 MBPCKEZNJVJYTC-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
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- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
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- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JWSIZPAOIFLWKM-UHFFFAOYSA-N [3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-[3-(dimethylamino)-4-hydroxypyrrolidin-1-yl]methanone Chemical compound CN(C)C1CN(CC1O)C(=O)c1cccc(Oc2cc(CN)cc(n2)C(F)(F)F)c1 JWSIZPAOIFLWKM-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- QBHWPVJPWQGYDS-UHFFFAOYSA-N hexaphenylbenzene Chemical compound C1=CC=CC=C1C(C(=C(C=1C=CC=CC=1)C(C=1C=CC=CC=1)=C1C=2C=CC=CC=2)C=2C=CC=CC=2)=C1C1=CC=CC=C1 QBHWPVJPWQGYDS-UHFFFAOYSA-N 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- KBDFJGUYFOEMIQ-UHFFFAOYSA-M lithium 2-(6-hydroxy-6-pyridin-2-yl-1H-pyridin-2-yl)phenolate Chemical compound OC1(NC(=CC=C1)C1=C(C=CC=C1)[O-])C1=NC=CC=C1.[Li+] KBDFJGUYFOEMIQ-UHFFFAOYSA-M 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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Abstract
本发明提供可成为蓝色元件的发光材料的含硼化合物及使用其的有机EL元件。该含硼化合物具有由下述通式(1)表示的骨架。通式(1)中,X分别独立地表示‑NR1‑、‑CR2R3‑、‑O‑或‑S‑。在上述‑NR1‑及‑CR2R3‑中,R1~R3分别独立地为氢、氘、碳原子数为1~6的烷基或核原子数为5~30的芳基,R2及R3也可以彼此连结而形成环。Cy1表示核原子数为5~30的芳基。由通式(1)表示的骨架的氢的一部分或全部也可以被氘、卤素、碳原子数为1~6的烷基、核原子数为5~30的芳基、取代或非取代的硅烷基(silyl group)、取代或非取代的氨基或者氰基所取代。
Description
技术领域
本发明涉及具有包含作为掺杂材料的含硼化合物和作为基质材料的蒽衍生物的发光层的有机EL元件。
背景技术
就有机EL元件来说,通过在一对电极之间施加电压,空穴从阳极、电子从阴极分别注入包含有机化合物作为发光材料的发光层,所注入的电子与空穴复合,由此在发光性的有机化合物中形成激子,能够由被激发的有机化合物得到发光。即,由于为自发光性元件,因此有机EL元件与液晶元件相比明亮并且目视确认性优异,能够实现鲜明的显示。
就有机EL元件来说,有效利用作为自发光性元件的优点,其作为高发光效率、高画质、低耗电、长寿命以及薄型设计性优异的发光元件而受到期待。
为了实现提高有机EL元件的性能,进行了如下操作:将发光层制成由基质中掺杂有发光材料作为掺杂剂的基质/掺杂剂形成的发光层。
就这样的发光层来说,能够由注入基质中的电荷高效地生成激子。并且,使所生成的激子的能量转移至掺杂剂,能够由掺杂剂得到高效率的发光。
关于发光层进行了各种研究,还在继续探索适当的发光材料。例如,就通过硼、氧等将多个芳香族环连结而得到的多环芳香族化合物来说,有以下报道:由于包含杂原子的六元环的芳香族性低,因此伴随共轭体系的扩张的HOMO-LUMO能隙的减少小,可得到大的带隙Eg;就包含杂原子的多环芳香族化合物来说,通过三重激发态(T1)下的SOMO1及SOMO2的局部存在化而使两轨道之间的交换相互作用变小,因此三重激发态(T1)与单重激发态(S1)的能量差小,显示出热活性型延迟荧光(国际公开第2015/102118A1号)。
另外,还公开了通过硼及氮将多个芳香族环连结而得到的多环芳香族化合物(国际公开第2017/188111A1号)。国际公开第2017/188111A1号报道了:就组合使用了上述多环芳香族化合物及与其对应地可得到最佳发光特性的蒽系化合物的有机EL元件来说,其耗电量低、量子效率优异。
发明内容
本发明的目的是提供蓝色发光的新颖的硼化合物,还提供含有该硼化合物的长寿命的有机EL元件。
本发明的含硼化合物具有由下述通式(1)表示的骨架。
通式(1)中,X分别独立地表示-NR1-、-CR2R3-、-O-或-S-。在上述-NR1-及-CR2R3-中,R1~R3分别独立地为氢、氘、碳原子数为1~6的烷基或核原子数为5~30的芳基,R2及R3也可以互相连结而形成环。
Cy1表示核原子数为5~30的芳基。
由通式(1)表示的骨架的氢的一部分或全部也可以被氘、卤素、碳原子数为1~6的烷基、核原子数为5~30的芳基、取代或非取代的硅烷基(silyl group)、取代或非取代的氨基或者氰基所取代。
上述Cy1具体来说为由下述结构式表示的苯环、萘环或喹喔啉环。式中,波浪线表示键合位置。
本发明的含硼化合物具有由下述通式(2)表示的骨架。
通式(2)中,R1~R2分别独立地表示碳原子数为1~6的烷基或核原子数为5~30的芳基。
由通式(2)表示的骨架的氢的一部分或全部也可以被氘、卤素、碳原子数为1~6的烷基、核原子数为5~30的芳基、取代或非取代的硅烷基(silyl group)、取代或非取代的氨基或者氰基所取代。
本发明的有机EL元件含有上述含硼化合物。
本发明的有机EL元件在发光带中含有上述含硼化合物。
本发明的有机EL元件在发光层中含有上述含硼化合物。
本发明的有机EL元件在发光层中含有0.1~20重量%的上述含硼化合物。
就上述有机EL元件来说,优选使用蒽衍生物作为发光层的基质。
就上述有机EL元件来说,优选使用具有由下述通式(3)表示的骨架的蒽衍生物作为发光层的基质。
通式(3)中,Y表示芳香族环式取代基或非芳香族环式取代基,Cy2表示核碳原子数为6~12的芳基,优选表示苯环或萘环。
本发明的含硼化合物是具有在分子内包含硼的七元环结构的新化合物。将上述含硼化合物作为蓝色掺杂剂用于发光层的有机EL元件与现有的蓝色元件相比,发光效率和寿命大幅提高。
附图说明
图1表示本发明的有机EL元件的构成。
具体实施方式
以下,对本发明进行详细说明。
本发明的含硼化合物具有由通式(1)表示的骨架。
通式(1)中,X分别独立地表示氨基(-NR1-)、亚烷基(-CR2R3-)、醚键(-O-)或硫醚键(-S-)。在上述-NR1-及CR2R3-中,R1~R3分别独立地为氢、氘、碳原子数为1~6的烷基或核原子数为5~30的芳基。
由通式(1)表示的骨架的氢的一部分或全部也可以被氘、卤素、碳原子数为1~6的烷基、核原子数为5~30的芳基、取代或非取代的硅烷基(silyl group)、取代或非取代的氨基或者氰基所取代。
对于碳原子数为1~6的烷基,可列举出直链或包含支链的烷基。具体来说,有甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、新戊基、异戊基、仲戊基、3-戊基、叔戊基、正己基、2-甲基戊基、3-甲基戊基、2,2-二甲基丁基及2,3-二甲基丁基等。
对于核原子数为5~30的芳基,可列举出单环式或缩合多环式并且也可以具有取代基的芳香族烃基。具体来说,有:苯基、1-萘基、2-萘基、对甲氧基苯基、对叔丁基苯基、对甲苯基、间甲苯基、邻甲苯基、五氟苯基、菲基、芘基、芴基、荧蒽基、吡啶基、喹喔啉基、吡咯基、吲哚基、咔唑基、咪唑基、苯并咪唑基、呋喃基、苯并呋喃基、二苯并呋喃基、硫代苯基、苯并硫代苯基、二苯并硫代苯基、苯并噁唑基及苯并噻噁唑基等。
R2及R3也可以互相连结而形成例如环己基之类的环。
Cy1表示核原子数为5~30的芳基。上述的例示中,Cy1优选苯环、萘环或喹喔啉环。下述结构式中,波浪线表示键合位置。
本发明的含硼化合物也包含具有由通式(2)表示的骨架的形态。
通式(2)中,R4~R5分别独立地表示碳原子数为1~6的烷基或核原子数为5~30的芳基。
碳原子数为1~6的烷基及核原子数为5~30的芳基与对于通式(1)的碳原子数为1~6的烷基及核原子数为5~30的芳基进行了说明的基团相同。但是,就核原子数为5~30的芳基来说,在R4或R5为苯基的情况下,位于该苯基的邻位的碳也可以与C1或C2连结。此外,C1及C2表示碳原子。
由通式(2)表示的骨架的氢的一部分或全部也可以被氘、卤素、碳原子数为1~6的烷基、核原子数为5~30的芳基、取代或非取代的硅烷基(silyl group)、取代或非取代的氨基或者氰基所取代。
具体来说,本发明的含硼化合物为具有下述结构式的化合物。
本发明的硼化合物具有π共轭体系扩展的结构。已知具有π共轭体系的分子在可见光区域具有光吸收带,其大多可作为色素来发挥作用。另一方面,若π共轭体系扩展,则HOMO上升,LUMO下降,HOMO-LUMO之间的能隙(带隙Eg)变小。本发明发现了:就由通式(1)或(2)表示的硼化合物那样的将芳香环以硼、氧、氮或硫之类的杂元素连结而得到的多环芳香族化合物来说,由于含杂元素的部分而使带隙Eg的减少得以抑制,因此具有大的带隙Eg。
本发明的硼化合物具有高的三重激发能量(ET)。另外,就上述硼化合物来说,由于通过杂元素的电子微扰而使三重激发态的SOMO1-SOMO2之间的交换相互作用变小,因此单重激发态(ES)与三重激发态(ET)的能隙(ΔEST)小。
在本发明中,对与分子加成的官能团进行研究来改变电子性质,由此调节带隙Eg并且尽可能减小单重-三重能隙(ΔEST),从而能够使暂时转移至三重激发态(ET)的能量再次恢复成单重激发态(ES),能够取出高效的荧光。
本发明的硼化合物可以通过各种公知方法进行合成。作为一个例子,示出作为本发明的硼化合物之一的化合物A的合成方法。
在3,3”-二溴-邻三联苯及苯胺中添加叔丁醇钠(tBuONa)及脱水甲苯,进行了片刻氮鼓泡,然后添加三(二苄叉丙酮)二钯(0)(Pd2(dba)3)及三叔丁基鏻四氟硼酸盐(tBu3PH+BF4 -),通过交叉偶联反应,得到化合物1-1。接着,在化合物1-1中添加1,3-二溴-2-氯苯及硝基苯,通过在铜催化剂及碳酸钾(K2CO3)的存在下使它们反应,得到化合物1-2。通过在化合物1-2中添加正丁基锂、叔丁基苯、三溴化硼(BBr3)及N,N-二异丙基乙基胺(EtN(iPr)2)并使它们反应,以良好的收率得到化合物A。
本发明的有机EL元件使用上述硼化合物而形成。上述含硼化合物包含于有机EL元件的发光带中。所谓发光带是空穴与电子复合而产生发光的区域,但发光层5在多数情况下相当于发光带。
有机EL元件是将一层或两层以上的有机层层叠于电极之间而成的结构,有例如“阳极1/空穴注入层2/空穴输送层3/发光层5/电子输送层7/电子注入层8/阴极”、“阳极1/空穴输送层3/发光层5/电子输送层7/电子注入层8/阴极9”、“阳极1/空穴注入层2/发光层5/电子输送层7/电子注入层8/阴极9”、“阳极1/空穴注入层2/空穴输送层3/发光层5/电子注入层8/阴极9”、“阳极1/空穴注入层2/空穴输送层3/发光层5/电子输送层7/阴极9”、“阳极1/发光层5/电子输送层7/电子注入层8/阴极9”、“阳极1/空穴输送层3/发光层5/电子注入层8/阴极9“、“阳极1/空穴输送层3/发光层5/电子输送层7/阴极9”、“阳极1/空穴注入层2/发光层5/电子注入层8/阴极9”、“阳极1/空穴注入层2/发光层5/电子输送层7/阴极9”、“阳极1/发光层5/电子输送层7/阴极9”以及“阳极1/发光层5/电子注入层8/阴极9”的构成方式。在本发明的实施例中,如图1中所示的那样,示出了在上述构成中追加了电子势垒层4以及空穴势垒层6的以“阳极1/空穴注入层2/空穴输送层3/电子势垒层4/发光层5/空穴势垒层6/电子输送层7/电子注入层8/阴极9”的顺序依次层叠而成的结构。此外,所谓有机层是指除了电极1、9以外的层即空穴注入层2、空穴输送层3、电子势垒层4、发光层5、空穴势垒层6、电子输送层7及电子注入层8等。
对于基板,使用透明且平滑并且具有至少70%以上的总光线透射率的基板,具体来说使用作为柔性的透明基板的几微米厚的玻璃基板、特殊的透明塑料等。
形成于基板上的阳极1、空穴注入层2、空穴输送层3、电子势垒层4、发光层5、空穴势垒层6、电子输送层7、电子注入层8、阴极9之类的薄膜通过真空蒸镀法或涂布法而层叠。在使用真空蒸镀法的情况下,通常是在减压至10-3Pa以下的气氛中加热蒸镀物而进行。各层的膜厚根据层的种类、所使用的材料而不同,通常阳极1及阴极9为100nm左右,包括发光层5在内的其他有机层小于50nm。
对于阳极1,使用功函数大并且总光线透射率通常为80%以上的材料。具体来说,为了使由阳极1发出的光透射,使用氧化铟锡(ITO)、氧化锌(ZnO)之类的透明导电性陶瓷、聚噻吩-聚苯乙烯磺酸(PEDOT-PSS)、聚苯胺之类的透明导电性高分子、其他透明导电性材料。
为了将空穴高效地由阳极1输送至发光层5,在阳极1与发光层5之间设置空穴注入层2、空穴输送层3。
对于形成空穴注入层2的空穴注入材料,例如可列举出:含(聚(亚芳基醚酮)的三苯基胺(KLHIP:PPBI)、1,4,5,8,9,11-六氮杂三苯六甲腈(HATCN)及PEDOT-PSS等。由这些材料形成的空穴注入层2也被称为聚合物缓冲层,发挥降低有机EL元件的驱动电压的效果。
空穴输送层3是设置于阳极1与发光层5之间并且用于将空穴高效地由阳极1输送至发光层5的层。对于空穴输送材料,使用电离势小的材料即容易由HOMO激发电子、容易生成空穴的材料。例如,可列举出:聚(9,9-二辛基芴基-co-N-(4-丁基苯基)二苯基胺)(TFB)、4,4’-环己基双[N,N-双(4-甲基苯基)苯胺](TAPC)、N,N’-二苯基-N,N’-二(间甲苯基)联苯胺(TPD)、N,N’-二(1-萘基)-N,N’-二苯基联苯胺(NPD)、4DBFHPB(以六苯基苯作为中心骨架并且以二苯并呋喃封端的芳基胺衍生物)、4,4’,4”-三-9-咔唑基三苯基胺(TCTA)及4,4’,4”-三[苯基(间甲苯基)氨基]三苯基胺)等。
对于发光层5,与有机EL元件中所使用的其他发光层相同地优选与发光材料一起并用基质。对于基质,只要是使来自空穴输送层3、电子输送层7的电荷注入势垒为最小限度、将电荷封入发光层5中并且防止发光激子的猝灭的材料,则可以广泛使用公知的材料,本发明优选使用由下述通式(3)表示的蒽衍生物。
在通式(3)中,蒽骨架的九位(或十位)的碳与二苯并呋喃部位的1~4位中的任一个碳键合。
Y表示芳香族环式取代基或非芳香族环式取代基。芳香族环式取代基或非芳香族环式取代基优选为苯基、联苯基、萘基及二苯并呋喃基等,更优选为苯基、1-联苯基及1-萘基及2-二苯并呋喃基等。
Cy2表示核碳原子数为6~12的芳基。核碳原子数为6~12的芳基具体来说为苯环或萘环。即,蒽骨架的十位(或九位)具有二苯并呋喃或苯并萘呋喃的结构。
由通式(3)表示的蒽衍生物优选具有下述结构式。
这些蒽衍生物可以单独使用一种,也可以将两种以上混合使用。
基质的添加量优选为发光层5用材料整体的50~99.9重量%,更优选为80~95重量%。
在发光层5与空穴输送层3之间也可以适当设置电子势垒层4。通过设置电子势垒层4,将电子封入发光层内,从而提高发光层中的电荷的复合概率,能够使发光效率提高。对于形成电子势垒层4的电子势垒材料,使用单胺衍生物等。
为了将电子高效地由阴极9输送至发光层5,在阴极9与发光层5之间设置有空穴势垒层6、电子输送层7。对于形成电子输送层7的电子输送材料,例如可列举出:1,4-双(1,10-菲咯啉-2-基)苯(DPB)、8-羟基喹啉锂(Liq)、4,6-双(3,5-二(吡啶-3-基)苯基)-2-甲基嘧啶(B3PymPm)、4,6-双(3,5-二(吡啶-4-基)苯基)-2-苯基嘧啶(B4PyPPm)、2-(4-联苯基)-5-(对叔丁基苯基)-1,3,4-噁二唑(tBu-PBD)、1,3-双[5-(4-叔丁基苯基)-2-[1,3,4]噁二唑基]苯(OXD-7)、3-(联苯-4-基)-5-(4-叔丁基苯基)-4-苯基-4H-1,2,4-***(TAZ)、浴铜灵(BCP)、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯(TPBi)及3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-***(TAZ)等。它们之中,优选DPB及Liq的混合层等。
空穴势垒层6是用于将空穴封入发光层5内而提高发光层5中的电荷的复合概率、使发光效率提高的层。对于形成空穴势垒层6的空穴势垒材料,使用DBT-TRZ等。空穴势垒层6及电子输送层7的膜厚通常为3~50nm,可以根据目标设计而适当变更。
对于形成电子注入层8的电子注入材料,例如可列举出:氟化锂(LiF)及2-羟基-(2,2’)-联吡啶-6-基-苯酚基合锂(Libpp)等。
对于阴极9,使用功函数低(4eV以下)并且化学稳定的材料。具体来说,使用Al、MgAg合金、Al与碱金属的合金(例如AlLi)或AlCa合金之类的阴极材料。这些阴极材料例如通过电阻加热蒸镀法、电子束蒸镀法、溅射法或离子镀法而成膜。
实施例
以下,基于实施例对本发明进行进一步具体说明,但本发明并不限于下述实施例。
〔实施例1〕
[含硼化合物的合成]
(i)化合物1-1的合成
在具备搅拌件的300mL四口烧瓶中加入3,3”-二溴-邻三联苯10.00g(25.8mmol)、特级苯胺2.40g(25.8mmol)、叔丁醇钠12.40g(129mmol)、及脱水甲苯250mL并进行了1小时氮鼓泡。向其中加入三(二苄叉丙酮)二钯(0)0.95g(1.0mmol)及三叔丁基鏻四氟硼酸盐0.58g(2.0mmol),进行12小时回流搅拌。对于反应混合物通过TLC确认到原料的消失。将反应混合物以甲苯萃取,进行盐洗,利用MgSO4进行干燥,然后将溶剂蒸馏除去。对所得到的残渣以硅胶柱色谱法进行纯化,由此以收率为62%得到了6.60g(16.0mmol)的化合物1-1。
(ii)化合物1-2的合成
在具备搅拌件的100mL四口烧瓶中加入6.60g(16.0mmol)的化合物1-1、1,3-二溴-2-氯苯4.75g(17.6mmol)、铜粉末1.00g(15.7mmol)、碳酸钾6.60g(47.8mmol)及硝基苯100mL,在氮气氛下进行了12小时回流搅拌。通过TLC确认到反应混合物,然后将反应混合物恢复至室温。将有机层以二氯甲烷萃取,进行盐洗,利用MgSO4进行干燥,然后将溶剂蒸馏除去。对所得到的残渣以硅胶柱色谱法进行纯化,由此以收率为31%得到了2.58g(5.00mmol)的化合物1-2。
(iii)化合物A(含硼化合物)的合成
在具备搅拌件的100mL四口烧瓶中加入2.58mg(5.00mmol)的化合物1-2及叔丁基苯50mL,在氮气氛下冷却至0℃以下。向其中添加了正丁基锂的己烷溶液3.3mL(1.64M、5.4mmol),然后在室温下搅拌了2小时。之后在0℃以下添加三溴化硼0.71mL(7.5mmol),在室温下搅拌了20小时。之后在0℃以下添加了N,N-二异丙基乙基胺1.74mL(10.0mmol)。通过在氮气氛下在100℃下加热搅拌2小时而将己烷蒸馏除去,然后在130℃下加热搅拌了8小时。进一步在150℃下加热搅拌了20小时,然后冷却至0℃以下,添加了N,N-二异丙基乙胺1.74mL(10.0mmol)。加入甲苯,利用弗罗里硅土进行过滤,将溶剂蒸馏除去。对所得到的残渣以硅胶柱色谱法进行纯化,以收率为32%得到了790mg(1.60mmol)的化合物A。
就所得到的化合物A来说,通过FD-MS(场解吸质量谱)的测定观测到m/Z=494.4的质谱图,因此化合物A被鉴定成记载的结构的化合物。
[元件的制作及评价]
以将通过溅射制成了180nm厚度的ITO研磨至150nm而得到的26mm×28mm×0.7mm的玻璃基板(Opto Science株式会社制造)作为透明支撑基板。
将该透明支撑基板固定于市售的蒸镀装置(昭和真空株式会社制造)的基板支架上,安装了加有HIM(空穴注入材料)的钼制蒸镀用舟皿、加有HTM(空穴输送材料)的钼制蒸镀用舟皿、加有EBL(电子势垒材料)的钼制蒸镀用舟皿、加有BH1(基质)的钼制蒸镀用舟皿、加有本发明的化合物A的钼制蒸镀用舟皿、加有HBL(空穴势垒材料)的钼制蒸镀用舟皿、加有ETM(电子输送材料)的钼制蒸镀用舟皿、加有LiF的钼制蒸镀用舟皿及加有铝的钨制蒸镀用舟皿。以下示出各个材料的结构式。
在透明支撑基板的ITO膜上依次形成了下述各层。将真空槽减压至5×10-4Pa为止,首先,对加有HIM的蒸镀用舟皿进行加热并以膜厚成为5nm的方式进行蒸镀而形成了空穴注入层2。接着,对加有HTM的蒸镀用舟皿进行加热并以膜厚成为105nm的方式进行蒸镀而形成了空穴输送层3。进而,对加有EBL的蒸镀用舟皿进行加热并以膜厚成为20nm的方式蒸镀而形成了电子势垒层4。
接着,对加有BH1的蒸镀用舟皿和加有化合物A的蒸镀用舟皿同时进行加热并以膜厚成为25nm的方式进行蒸镀而形成了发光层5。以BH1与化合物A之重量比成为大约80比20的方式调整了蒸镀速度。
接着,对加有HBL的蒸镀用舟皿进行加热并以膜厚成为20nm的方式进行蒸镀而形成了空穴势垒层6。接着,对加有ETM的蒸镀用舟皿进行加热并以膜厚成为10nm的方式进行蒸镀而形成了电子输送层7。
各层的蒸镀速度为0.01~2nm/秒。
之后,对加有作为电子注入层8的材料的LiF的蒸镀用舟皿进行加热并以膜厚成为1nm的方式按照0.01~0.1nm/秒的蒸镀速度进行蒸镀。接着,通过对加有铝的蒸镀用舟皿进行加热并以成为100nm的方式按照0.01~2nm/秒的蒸镀速度进行蒸镀而形成了阴极9,得到了有机EL元件。
在将ITO电极作为阳极1并将LiF/铝电极作为阴极9而施加直流电压的情况下,得到了蓝色发光。
在对其以初始亮度1000nit进行恒流驱动时,对直至亮度成为95%为止的时间进行了测定。
〔比较例1〕
除了使用了由下述结构式表示的化合物来代替化合物A以外,与实施例1完全相同地制得了元件。
在将ITO电极作为阳极并将LiF/铝电极作为阴极而施加直流电压的情况下,得到了蓝色发光。
在将其以初始亮度1000nit进行了恒流驱动时,对直至亮度成为95%为止的时间进行了测定。
表1
以比较例1中测得的时间为100时的相对值 | |
实施例1 | 145 |
比较例1 | 100 |
发现了本发明的化合物与公知技术相比可维持长寿命的蓝色发光。
Claims (8)
3.一种有机EL元件,其含有权利要求1或2所述的含硼化合物。
4.一种有机EL元件,其在发光带中含有权利要求1或2所述的含硼化合物。
5.一种有机EL元件,其在发光层中含有权利要求1或2所述的含硼化合物。
6.一种有机EL元件,其在发光层中含有0.1~20重量%的权利要求1或2所述的含硼化合物。
7.根据权利要求6所述的有机EL元件,其特征在于,其使用蒽衍生物作为发光层的基质。
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