CN102850177A - 联三伸苯基衍生物在有机电致发光组件上的应用 - Google Patents
联三伸苯基衍生物在有机电致发光组件上的应用 Download PDFInfo
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- CN102850177A CN102850177A CN2011102540053A CN201110254005A CN102850177A CN 102850177 A CN102850177 A CN 102850177A CN 2011102540053 A CN2011102540053 A CN 2011102540053A CN 201110254005 A CN201110254005 A CN 201110254005A CN 102850177 A CN102850177 A CN 102850177A
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- Prior art keywords
- phenyl
- connection
- styryl
- stretched
- group
- Prior art date
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- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 150000002431 hydrogen Chemical group 0.000 claims abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- 125000003368 amide group Chemical group 0.000 claims description 14
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 13
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 10
- 125000005504 styryl group Chemical group 0.000 claims description 9
- 101001016849 Mus musculus Heat shock protein HSP 90-alpha Proteins 0.000 claims description 5
- 101000985444 Mus musculus Heat shock protein HSP 90-beta Proteins 0.000 claims description 5
- MOLYOWYXBFSSPK-CCEZHUSRSA-N 2-[4-[(e)-2-phenylethenyl]phenyl]triphenylene Chemical group C=1C=C(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)C=CC=1\C=C\C1=CC=CC=C1 MOLYOWYXBFSSPK-CCEZHUSRSA-N 0.000 claims description 3
- JUHGSJFZYNMXHF-FOCLMDBBSA-N 4-methyl-n-(4-methylphenyl)-n-[4-[(e)-2-(4-triphenylen-2-ylphenyl)ethenyl]phenyl]aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)=CC=1)C1=CC=C(C)C=C1 JUHGSJFZYNMXHF-FOCLMDBBSA-N 0.000 claims description 3
- BDNDYWZDKFMZQQ-FOCLMDBBSA-N 9-ethyl-3-[(e)-2-(4-triphenylen-2-ylphenyl)ethenyl]carbazole Chemical compound C1=CC=C2C3=CC(C4=CC=C(C=C4)/C=C/C=4C=C5C6=CC=CC=C6N(C5=CC=4)CC)=CC=C3C3=CC=CC=C3C2=C1 BDNDYWZDKFMZQQ-FOCLMDBBSA-N 0.000 claims description 3
- PZGIQGRKSZZAGR-QURGRASLSA-N n-phenyl-n-[4-[(e)-2-(4-triphenylen-2-ylphenyl)ethenyl]phenyl]naphthalen-1-amine Chemical compound C=1C=C(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)C=CC=1\C=C\C(C=C1)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 PZGIQGRKSZZAGR-QURGRASLSA-N 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims 4
- 125000005580 triphenylene group Chemical group 0.000 claims 4
- NZGAKYAQARWTLT-FMQUCBEESA-N n,n-diphenyl-4-[(e)-2-(4-triphenylen-2-ylphenyl)ethenyl]aniline Chemical compound C=1C=C(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)C=CC=1\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 NZGAKYAQARWTLT-FMQUCBEESA-N 0.000 claims 2
- 150000001491 aromatic compounds Chemical class 0.000 abstract 2
- 239000002019 doping agent Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 35
- 239000010410 layer Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 21
- -1 Ph) Chemical group 0.000 description 14
- 238000010792 warming Methods 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910004298 SiO 2 Inorganic materials 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- QBFQLEVWHCQDIR-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-2-pyrrolidin-1-ylpropan-1-one Chemical compound CC1=C(C=CC(=C1)C)C(C(C)N1CCCC1)=O QBFQLEVWHCQDIR-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 6
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000006392 deoxygenation reaction Methods 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 0 *C(Cc1cccc(-c(cc2)cc3c2c2ccccc2c2c3cccc2)c1)=C(*)[Al] Chemical compound *C(Cc1cccc(-c(cc2)cc3c2c2ccccc2c2c3cccc2)c1)=C(*)[Al] 0.000 description 2
- YNOMVRSHBGESCP-UHFFFAOYSA-N 2-(2,2-diphenylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 YNOMVRSHBGESCP-UHFFFAOYSA-N 0.000 description 2
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 2
- RAPHUPWIHDYTKU-WXUKJITCSA-N 9-ethyl-3-[(e)-2-[4-[4-[(e)-2-(9-ethylcarbazol-3-yl)ethenyl]phenyl]phenyl]ethenyl]carbazole Chemical compound C1=CC=C2C3=CC(/C=C/C4=CC=C(C=C4)C4=CC=C(C=C4)/C=C/C=4C=C5C6=CC=CC=C6N(C5=CC=4)CC)=CC=C3N(CC)C2=C1 RAPHUPWIHDYTKU-WXUKJITCSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000002769 thiazolinyl group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004149 thio group Chemical group *S* 0.000 description 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- VUQVJIUBUPPCDB-UHFFFAOYSA-N (1-bromo-2,2-diphenylethenyl)benzene Chemical compound C=1C=CC=CC=1C(Br)=C(C=1C=CC=CC=1)C1=CC=CC=C1 VUQVJIUBUPPCDB-UHFFFAOYSA-N 0.000 description 1
- QRDVTIMUEDYLOC-UHFFFAOYSA-N (2-bromo-1-phenylethenyl)benzene Chemical compound C=1C=CC=CC=1C(=CBr)C1=CC=CC=C1 QRDVTIMUEDYLOC-UHFFFAOYSA-N 0.000 description 1
- JWJGPHUIIWREQT-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-3-iodobenzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC(I)=C1 JWJGPHUIIWREQT-UHFFFAOYSA-N 0.000 description 1
- ACYSYNIYTMHNSY-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-4-iodobenzene Chemical compound CCOP(=O)(OCC)CC1=CC=C(I)C=C1 ACYSYNIYTMHNSY-UHFFFAOYSA-N 0.000 description 1
- GMKOUIDVOTWKRM-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1.BrC1=CC=C(I)C=C1 GMKOUIDVOTWKRM-UHFFFAOYSA-N 0.000 description 1
- PCGQOYPJAJECND-UHFFFAOYSA-N 1-phenyltriphenylene Chemical class C1=CC=CC=C1C1=CC=CC2=C(C=CC=C3)C3=C(C=CC=C3)C3=C12 PCGQOYPJAJECND-UHFFFAOYSA-N 0.000 description 1
- HXHXQDBJVTYWSG-UHFFFAOYSA-N 2,2-bis(4-bromophenyl)-1,3,4-triphenyl-1H-triphenylene Chemical compound C1=CC=C(C=C1)C2C3=C(C4=CC=CC=C4C5=CC=CC=C53)C(=C(C2(C6=CC=C(C=C6)Br)C7=CC=C(C=C7)Br)C8=CC=CC=C8)C9=CC=CC=C9 HXHXQDBJVTYWSG-UHFFFAOYSA-N 0.000 description 1
- VAKKDBBXNSOJMK-UHFFFAOYSA-N 2,2-diphenylethenylboronic acid Chemical compound C=1C=CC=CC=1C(=CB(O)O)C1=CC=CC=C1 VAKKDBBXNSOJMK-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
- XUPBCFRZAJIYKK-UHFFFAOYSA-N 2-[4-(1,2,2-triphenylethenyl)phenyl]triphenylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC(=CC=1)C=1C=C2C3=CC=CC=C3C3=CC=CC=C3C2=CC=1)C1=CC=CC=C1 XUPBCFRZAJIYKK-UHFFFAOYSA-N 0.000 description 1
- OHBRXOKTWQIZCK-UHFFFAOYSA-N 2-[4-(diethoxyphosphorylmethyl)phenyl]triphenylene Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1C1=CC=C(C=2C(=CC=CC=2)C=2C3=CC=CC=2)C3=C1 OHBRXOKTWQIZCK-UHFFFAOYSA-N 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- SBJDOWNOTSFHCV-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-(1,2,2-triphenylethenyl)-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 SBJDOWNOTSFHCV-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- RSQXKVWKJVUZDG-UHFFFAOYSA-N 9-bromophenanthrene Chemical compound C1=CC=C2C(Br)=CC3=CC=CC=C3C2=C1 RSQXKVWKJVUZDG-UHFFFAOYSA-N 0.000 description 1
- GLMRQKCCWWJHRG-UHFFFAOYSA-N BrC1=CC(=CC=C1)I.BrC1=CC(=CC=C1)I Chemical compound BrC1=CC(=CC=C1)I.BrC1=CC(=CC=C1)I GLMRQKCCWWJHRG-UHFFFAOYSA-N 0.000 description 1
- FWESVNIHRVSDDV-UHFFFAOYSA-N Brc(cc1)ccc1-c1ccc(c(cccc2)c2c2ccccc22)c2c1 Chemical compound Brc(cc1)ccc1-c1ccc(c(cccc2)c2c2ccccc22)c2c1 FWESVNIHRVSDDV-UHFFFAOYSA-N 0.000 description 1
- BTUUYCULZQYBDW-UHFFFAOYSA-N C(=O)C=1C=CC=2N(C3=CC=CC=C3C2C1)CC.C(=O)C=1C=CC=2N(C3=CC=CC=C3C2C1)CC Chemical compound C(=O)C=1C=CC=2N(C3=CC=CC=C3C2C1)CC.C(=O)C=1C=CC=2N(C3=CC=CC=C3C2C1)CC BTUUYCULZQYBDW-UHFFFAOYSA-N 0.000 description 1
- KHHXUOVJRIYOQZ-UHFFFAOYSA-N C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.C(CCC)P(CCCC)CCCC Chemical compound C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.C(CCC)P(CCCC)CCCC KHHXUOVJRIYOQZ-UHFFFAOYSA-N 0.000 description 1
- PWCHOVYZTJENOS-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)NC1=CC=CC2=CC=CC=C12 Chemical compound C1(=CC=CC=C1)NC1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)NC1=CC=CC2=CC=CC=C12 PWCHOVYZTJENOS-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- ACUGBZSUIIJBLO-UHFFFAOYSA-N C=1C=C(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical group C=1C=C(C=2C=C3C4=CC=CC=C4C4=CC=CC=C4C3=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 ACUGBZSUIIJBLO-UHFFFAOYSA-N 0.000 description 1
- VSOCZSRIHDJQOU-JGHOTKKVSA-N CC1C=Cc2c(cccc3)c3c(cc(cc3)/C(/C=C\C)=C/C)c3c2C1 Chemical compound CC1C=Cc2c(cccc3)c3c(cc(cc3)/C(/C=C\C)=C/C)c3c2C1 VSOCZSRIHDJQOU-JGHOTKKVSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N CCc1ccccc1 Chemical compound CCc1ccccc1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- VKIJXFIYBAYHOE-VOTSOKGWSA-N [(e)-2-phenylethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=CC=C1 VKIJXFIYBAYHOE-VOTSOKGWSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004467 aryl imino group Chemical group 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- PCDYAMLWUWSNCX-UHFFFAOYSA-N benzaldehyde 4-(N-phenylanilino)benzaldehyde Chemical compound C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=C(C=O)C=C1.C(C1=CC=CC=C1)=O PCDYAMLWUWSNCX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 125000005266 diarylamine group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WGLLSSPDPJPLOR-UHFFFAOYSA-N tetramethylethylene Natural products CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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Abstract
一种联三伸苯基芳香族化合物,其具有化学式(1),其中Ar为芳香族化合物,n为1至3,R1-R13及R系选自由氢、卤素、氰基、三氟甲烷基、胺基、C1-C10烷基、C2-C10烯基、C2-C10炔基、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基、C1-C20杂环烯基、芳基及杂芳基所组成的群组。本发明的联三伸苯基衍生物可作为有机发光二极管的发光层中的主体发光材料或是掺杂物。此外本发明亦提供一种有机发光二极管。
Description
技术领域
本发明是关于一种化合物及其有机发光二极管,尤其是一种联三伸苯基衍生物及其有机发光二极管。
背景技术
由于有机发光二极管(Organic light emitting diode,OLED)运用于平面显示器相当具有优势,因此许多研究学者都对OLED相当有兴趣。其中发展稳定及高效率的三原色(红、绿、蓝)发光材料与发光组件对于OLED发展为商业产品是非常重要的。发展有机发光二极管组件的一项重要要求为发展RGB(红绿蓝)发光组件以符合彩色平面显示器的需求。
特别是寻找有效率及寿命的蓝光电致发光材料,因为其为将OLED实现为显示及照明用途的重要组件。目前已有许多研究团队成功地制备有效率的蓝光荧光团(fluorophore)及其OLED。然而,到目前为止,色度y坐标(Commission Internationale d’Enclairage y coordinate value,CIEy))≤0.15且具寿命的有效率材料非常稀少。目前仍缺乏良好的有机发光二极管化合物以符合上述需求。
综合上述,目前亟需发展新颖的发光有机化合物,特别为深蓝光发光材料,可有效地用于低耗能的有机发光二极管组件。
发明内容
本发明的目的为提供一种新颖化合物及其在有机发光二极管的应用。
依据本发明的一实施例,一种联三伸苯基衍生物,具有化学式(1)的结构,其中Ar为芳香族化合物,n为1至3,R1-R13及R系选自由氢、卤素、氰基、三氟甲烷基、胺基、C1-C10烷基、C2-C10烯基、C2-C10炔基、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基、C1-C20杂环烯基、芳基及杂芳基所组成的群组。
依据本发明的另一实施例,一种有机发光二极管,包括一阴极、一阳极、设置于阴极及阳极之间的一发光层,以及设置于发光层及阴极之间的发光层,其中发光层包含上述的联三伸苯基衍生物。
本发明上述及其它实施方式、特性及优势可由附图及实施例的说明而可更加了解。
附图说明
图1为示意图显示具有联三伸苯基衍生物的有机发光二极管结构。
【主要组件符号说明】
1 阳极
2 阴极
3 发光层
4 电洞传输层
5 电子传输层
6 电洞阻挡层
7 电洞注入层
8 电子注入层
9 电子阻挡层
具体实施方式
一种联三伸苯基(Triphenylene)衍生物,具有下列化学式(1):
其中Ar为芳香族化合物,n为1至3,R1-R13及R系选自由氢、卤素、氰基、三氟甲烷基、胺基、C1-C10烷基、C2-C10烯基、C2-C10炔基、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基、C1-C20杂环烯基、芳基及杂芳基所组成的群组。
在一较佳实施例中,本发明的联三伸苯基衍生物具有下列化学式(1-1)、(1-2)。
在一较佳实施例中,本发明的联三伸苯基衍生物具有下列化学式(2)、(2-1)、(2-2)。
本案的Ar取代基较佳为苯基,其具有下列化学式(3):
其中R18-R22系选自由氢、卤素、氰基、三氟甲烷基、胺基、C1-C10烷基、C2-C10烯基(C2-C10 alkenyl)、C2-C10炔基(C2-C10 alkynyl)、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基、C1-C20杂环烯基、芳基及杂芳基所组成的群组。
此外在一实施例中,化学式(2)的Ar为具有含氮取代基的苯环,例如化学式(4)或(5),其中化学式(4)的Ar1及Ar2为芳香族化合物,而化学式(5)的R23系选自由氢、卤素、氰基、三氟甲烷基、胺基、C1-C10烷基、C2-C10烯基、C2-C10炔基、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基、C1-C20杂环烯基、芳基及杂芳基所组成的群组。
在此「芳基」指的是具有一或多个芳香环的碳氢基团。芳基基团范例包括苯基(phenyl,Ph)、亚苯基(phenylene)、萘基(naphthyl)、亚萘基(naphthylene)、芘基(pyrenyl)、蒽基(anthryl)、菲基(phenanthryl)及联三伸苯基(triphenyl enyl)。
「杂芳基」指的是具有一或多个芳香环的碳氢基团,且该芳香环包含至少一杂原子(例如,氮、氧或硫)。杂芳基基团范例可包括呋喃基(furyl)、亚呋喃基(furyl ene)、芴基(fluorenyl)、吡咯基(pyrrolyl)、噻吩基(thienyl)、恶唑基(oxazolyl)、咪唑基(imidazolyl)、噻唑基(thiazolyl)、吡啶基(pyridyl)、嘧啶基(pyrimidinyl)、喹唑啉基(quinazolinyl)、喹啉基(quinolyl)、异喹啉基(isoquinolyl)及吲哚基(indolyl)。
在此应注明的是烷基、烯基、炔基、环烷基、环烯基、杂环烷基、杂环烯基、芳基、以及杂芳基可包括经取代及未经取代的基团。
可能取代于环烷基、环烯基、杂环烷基、杂环烯基、芳基、以及杂芳基的取代基包含但不受限于C1-C10烷基、C2-C10烯基、C2-C10炔基、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基、C1-C20杂环烯基、C1-C10烷氧基、芳基、芳氧基、杂芳基、杂芳氧基、胺基、C1-C10烷胺基、C1-C20二烷胺基、芳胺基、二芳胺基、C1-C10烷基磺胺(C1-C10alkylsulfonamino)、芳基磺胺(arylsulfonamino)、C1-C10烷基亚胺(C1-C10 alkylimino)、芳基亚胺(arylimino)、C1-C10烷基磺亚胺(C1-C10alkylsulfonimino)、芳基磺亚胺(arylsulfonimino)、氢氧基、卤素、硫代基(thio)、C1-C10烷硫基、芳硫基、C1-C10烷磺酰基(alkylsulfonyl)、芳磺酰基(arylsulfonyl)、酰基胺(acylamino)、胺基酰(aminoacyl)、胺基硫酰(aminothioacyl)、酰胺基(amido)、脒基(amidino)、胍基(guanidine)、脲基(ureido)、硫脲基(thioureido)、腈基、硝基、亚硝基、叠氮基(azido)、酰基、硫酰基、酰氧基(acyloxy)、羧基、及羧酸酯等。另一方面,可能取代于烷基、烯基、或炔基的取代基包含除C1-C10烷基外的上述所有取代基。环烷基、环烯基、杂环烷基、杂环烯基、芳基、及杂芳基亦可互相稠合(fused)。
化合物合成
以下更加详细叙述本发明化合物的制备流程及光谱数据。
1,4-二氢-1,4-环氧联三伸苯基(1,4-Dihydro-1,4-epoxytriphenylene)(A)
将9-溴菲(9-bromophenanthrene)(18.6g,72.3mmol)与氨基钠(8.47g,217.0mmol)置于双颈瓶中,抽真空通入氮气后,加入无水THF(120mL)与呋喃(78.1mL,1.07mol),升温至70℃回流24小时,反应结束后,过滤去除盐类,浓缩,以管柱层析法(SiO2,正己烷)纯化,得白色固体14.7g,产率83%。
2-(4-溴苯基)三苯基(2-(4-Bromophenyl)triphenylene)(B)
将A(4.00g,16.4mmol)、1-溴-4-碘苯(1-bromo-4-iodobenzene)(4.64g,16.4mmol)或1-溴-3-碘苯(1-bromo-3-iodobenzene)、锌(10.72g,163.9mmol)与PdCl2(PPh3)2(1.16g,1.7mmo l)置于双颈瓶中,抽真空通入氮气后,加入无水甲苯(100mL)与三乙基胺(23.00mL,165.9mmol),升温至100℃反应24小时,反应结束后,过滤去除金属、浓缩,以管柱层析法(SiO2,正己烷)纯化,得白色固体3.90g,产率62%。
2-(2,2-二苯基乙烯基)-4,4,5,5-四甲基-1,3,2-二氧硼戊环(2-(2,2-Diphenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)(C)
将2,2-二苯基乙烯基溴(2,2-diphenylvinyl bromide)(6.50g,25.1mmol)置于反应瓶中,加热抽真空通氮气后,加入无水THF(40mL)搅拌溶解,降温至-78℃缓缓滴入n-BuLi(20.0mL,50.2mmol,2.50M溶于正己烷),维持-78℃搅拌1小时,加入硼酸三丁酯(tri-n-Butylborate)(15.0mL,55.5mmol)反应8小时。终止反应后,混合物与2.0M HCl(100mL)进行酸化3小时,以乙酸乙酯萃取,收集有机层,再以硫酸镁除水,浓缩静置待固体析出,过滤得白色固体2,2-二苯基乙烯基硼酸(2,2-diphenylvinyl boronic acid),再将其与2,3-二甲-2,3-丁二醇(频哪醇,pinacol)(4.25g,36.0mmol)溶于甲苯中,升温至回流反应2小时,反应结束后,减压浓缩去除溶剂,以管柱层析法(SiO2,正己烷/二氯甲烷=1/1)纯化,得无色液体4.10g,产率53%。
4,4,5,5-四甲基-2-(1,2,2-三苯基乙烯基)-1,3,2-二氧硼戊环(4,4,5,5-Tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane)(D)
将(2-乙烯基溴-1,1,2-三基)三苯((2-bromoethene-1,1,2-triyl)tribenzene)(5.00g,14.9mmol)置于反应瓶中,加热抽真空通氮气后,加入无水THF(50mL)搅拌溶解,降温至-78℃缓缓滴入n-BuLi(15.00mL,30.0mmol,2.50M溶于正己烷),维持-78℃搅拌1小时,加入B(OBu)3(11.0mL,40.8mmol)反应8小时。终止反应后,混合物与2.0M HCl(100mL)进行酸化2小时,以乙酸乙酯萃取,收集有机层,再以硫酸镁除水,浓缩静置待固体析出,过滤得白色固体1,2,2-三苯基乙烯基硼酸(1,2,2-triphenylvinylboronic acid),再将其与2,3-二甲-2,3-丁二醇(1.73g,14.6mmol)溶于甲苯中,升温至回流反应2小时,反应结束后,减压浓缩去除溶剂,以管柱层析法(SiO2,正己烷/乙酸乙酯=20/1)纯化,得白色固体2.41g,产率65%。
(E)-2-(4-苯乙烯基苯基)苯并((E)-2-(4-Styrylphenyl)triphenylene)(TSP)
将B(400mg,1.04mmol)或B1、(E)-苯乙烯基硼酸((E)-styrylboronic acid)(185mg,1.25mmol)、K2CO3(aq)(2.0M,4.00mL)与无水甲苯(12.0mL)置于双颈瓶中,进行除氧充氮气,于60℃下搅拌至完全溶解,开大氮气快速加入Pd(PPh3)4(120mg,0.1mmol),将反应升温至110℃搅拌48小时。反应结束后,减压浓缩去除溶剂,以水与甲醇冲洗固体,最后进行升华,温度为230℃,得白色固体317mg,产率75%。
1H NMR(400MHz,CDCl3):δ8.87(d,J=1.6Hz,1H),8.77-8.65(m,5H),7.92(dd,J=8.6,J=1.6Hz,1H),7.80(d,J=8.4Hz,2H),7.69-7.66(m,6H),7.56(d,J=8.0Hz,2H),7.38(t,J=7.6Hz,2H),7.28(d,J=7.2Hz,1H),7.20(s,2H).
13C NMR(100MHz,CDCl3):δ140.3,139.3,137.3,136.7,130.2,130.1,129.8,129.6,129.0,129.0,128.7,128.2,127.7,127.6,127.4,127.3,127.3,127.1,126.6,126.1,124.0,123.4.123.4,121.5.
HRMS(m/z):[M+]calcd.for C32H22,406.1722;found,406.1723
Anal.calcd for C32H22:C,94.55;H,5.45;found:C,94.42;H,5.50
2-(4-(2,2-二苯基乙烯基)苯基)苯并(2-(4-(2,2-Diphenylvinyl)phenyl)triphenylene)(TSDP)
将B(451mg,1.18mmol)、C(435mg,1.42mmol)、K2CO3(aq)(2.0M,8.00mL)与无水甲苯(24.0mL)置于双颈瓶中,进行除氧充氮气,于60℃下搅拌至完全溶解,开大氮气快速加入Pd(PPh3)4(139mg,0.12mmol),将反应升温至110℃搅拌48小时。反应结束后,减压浓缩去除溶剂,以水与甲醇冲洗固体,最后进行升华,温度为250℃,得白色固体388mg,产率68%。
1H NMR(400MHz,CDCl3):δ8.80(d,J=1.6Hz,1H),8.71-8.63(m,5H),7.85(dd,J=8.4,J=1.6Hz,1H),7.67-7.64(m,4H),7.60(d,J=8.4Hz,2H),7.39-7.27(m,10H),7.17(d,J=8.4Hz,2H),7.04(s,1H).
13C NMR(100MHz,CDCl3):δ143.4,142.9,140.5,139.2,139.2,136.8,130.4,130.2,130.1,130.1,129.8,129.8,129.6,128.9,128.8,128.3,127.7,127.6,127.6,127.6,127.3,127.3,127.2.126.8,126.0,123.9,123.4,123.3,121.4.
HRMS(m/z):[M+]calcd.for C38H26,482.2035;found,482.2036
Anal.calcd for C38H26:C,94.57;H,5.43;found:C,94.35;H,5.33
2-(4-(1,2,2-三苯基乙烯基)苯基)苯并(2-(4-(1,2,2-Triphenylvinyl)phenyl)triphenylene,TSTP)
将B(1.25g,3.26mmol)、D(1.37g,3.58mmol)、K2CO3(aq)(2.0M,8.00mL)与无水甲苯(24.0mL)置于双颈瓶中,进行除氧充氮气,于60℃下搅拌至完全溶解,开大氮气快速加入Pd(PPh3)4(381mg,0.33mmol),将反应升温至110℃搅拌48小时。反应结束后,减压浓缩去除溶剂,以水与甲醇冲洗固体,最后进行升华,温度为260℃,得白色固体1.50g,产率82%。
1H NMR(400MHz,CDCl3):δ8.80(s,1H),8.72-8.63(m,5H),7.84(d,J=8.4Hz,1H),7.66-7.64(m,4H),7.56(d,J=8.0Hz,2H),7.18-7.04(m,17H).
13C NMR(100MHz,CDCl3):δ143.7,143.1,141.2,140.5,139.3,138.7,132.0,131.4,131.4,130.0,129.8,129.8,129.6,128.8,127.8,127.7,127.7,127.3,127.2,126.5,126.5,126.1,123.8.123.3,121.4.
HRMS(m/z):[M+]calcd.for C44H30,558.2348;found,558.2344
Anal.calcd for C44H30:C,94.59;H,5.41;found:C,94.45;H,5.39
二乙基4-(2-联三伸苯基)苯甲基磷酸根(Diethyl 4-(triphenylen-2-yl)benzylphosphonate)(E)
将A(760mg,3.11mmol)、锌(1.85g,28.2mmol)与PdCl2(PPh3)2(198mg,0.28mmol)置于双颈瓶中,抽真空通入氮气后,加入无水甲苯(30mL)、1-溴-4-碘苯甲基磷酸根(diethyl 4-iodobenzylphosphonate)(0.65ml,2.82mmol)或1-溴-3-碘苯甲基磷酸根(diethyl3-iodobenzylphosphonate)与三乙基胺(3.91mL,28.2mmol),升温至110℃反应48小时,反应结束后,过滤去除金属、浓缩,以管柱层析法(SiO2,二氯甲烷)纯化,得化合物E白色固体0.90g,产率70%。
4-(萘基-1-yl(苯基)胺基)苯醛(4-(Naphthalen-1-yl(phenyl)amino)benzaldehyde)(F)
将4-溴苯醛(4-Bromobenzaldehyde)(1.00g,5.40mmol)、1-苯胺基萘(1-anilinonaphthalene)(1.42g,6.48mmol)、Pd(OAc)2(25mg,0.11mmol)与置于高压管中,抽真空通入氮气后,加入无水邻二甲苯(30mL)、三叔丁基膦(tri-tert-butylphosphine)(0.23ml,0.11mmol)与叔丁醇钠(623mg,6.48mmol),升温至120℃反应48小时,反应结束后,过滤去除金属、浓缩,正己烷/二氯甲烷=1/1)纯化,得黄色固体1.10g,产率63%。
4-甲基-N-苯基-N-p-甲苯基苯胺(4-Methyl-N-phenyl-N-p-tolylaniline)(G)
将4,4’-二甲基二苯基胺(4,4’-dimethyl diphenylamine)(0.99g,5.0mmol)、KOH(2.52g,45.0mmol)、CuCl(99mg,1.0mmol)与1,10-菲咯啉(1,10-phenanthroline)(180mg,1.0mmol)置于双颈瓶中,抽真空通入氮气后,加入甲苯(12mL)与碘苯(0.67mL,6.0mmol),升温至120℃反应12小时,反应结束后,过滤去除金属、浓缩,以管柱层析法(SiO2,正己烷/二氯甲烷=1/1)纯化,得白色固体916mg,产率67%。
1H NMR(400MHz,CDCl3):δ7.22-7.18(m,2H),7.07-6.91(m,11H),2.31(s,6H).
13C NMR(100MHz,CDCl3):δ148.3,145.4,132.3,129.8,129.0,124.4,122.9,121.7,20.8.
HRMS(m/z):[M+]calcd.for C20H19N,273.1517;found,273.1516
4-(二p-甲苯胺基)苯醛(4-(Dip-tolylamino)benzaldehyde)(H)
将DMF(N,N-二甲基甲酰胺,N,N-dimethylformamide)(6.0ml)置于双颈瓶中,抽真空通入氮气后,在冰浴下缓缓加入POCl3(0.86ml,5.27mmole),于0℃下搅拌30分钟后,再将溶于DMF(6.0ml)的G(1.2g,4.39mmole)缓缓加入混合,升温至70℃反应6小时,反应结束后,减压蒸馏去除溶剂,以管柱层析法(SiO2,正己烷/二氯甲烷=6/1)纯化,得黄色固体1.26g,产率95%。
1H NMR(400MHz,CDCl3):δ9.75(s,1H),7.62(d,J=8.8Hz,2H),7.13(d,J=8.0Hz,4H),7.05(d,J=8.0Hz,4H),6.92(d,J=8.8Hz,2H),2.33(s,6H).
13C NMR(100MHz,CDCl3):δ190.4,153.7,143.5,135.0,131.3,130.3,128.3,126.4,118.2,21.0.
HRMS(m/z):[M+]calcd.for C21H19NO,301.1467;found,301.1471
(E)-9-乙基-3-(4-(2-联三伸苯基)苯乙烯基)-9H-咔唑((E)-9-Ethyl-3-(4-(triphenylen-2-yl)styryl)-9H-carbazole)(TSCz)
将E(100mg,0.22mmol)或E1与N-乙基咔唑-3-甲醛(N-ethylcarbazole-3-carboxaldehyde)(59mg,0.26mmol)置于双颈瓶中,抽真空通入氮气后,加入无水THF(10mL);在冰浴下,将溶于THF(10ml)的叔丁醇钾(potassium tert-butoxide)(49mg,0.44mmole)缓缓加入混合,于0℃反应15分钟,反应结束后,减压浓缩去除溶剂,最后进行升华,温度为260℃,得黄色固体90mg,产率78%。
1H NMR(400MHz,CDCl3):δ8.89(d,J=1.6Hz,1H),8.78-8.65(m,5H),8.28(d,J=1.2Hz,1H),8.14(d,J=7.6Hz,1H),7.94(dd,J=8.4,J=2.0Hz,1H),7.83(d,J=8.0Hz,2H),7.73-7.65(m,7H),7.50-7.39(m,4H),7.27-7.23(m,2H),4.38(q,J=7.2Hz,2H),1.45(t,J=7.2Hz,3H).
13C NMR(100MHz,CDCl3):δ140.2,139.6,139.4,137.2,130.0,130.0,129.8,129.7,129.7,129.6,128.7,128.5,127.5,127.2,127.1,127.0,126.7,126.0,125.8,125.4,124.5,123.8,123.3.122.9,121.3,120.5,119.1,118.8,108.5,37.6,13.9.
HRMS(m/z):[M+]calcd.for C40H29N,523.2300;found,523.2299
Anal.calcd for C40H29N:C,91.74;H,5.58;N,2.67;found:C,91.37;H,5.80;N,2.43
(E)-N,N-二苯基-4-(4-(2-联三伸苯基)苯乙烯基)苯胺((E)-N,N-diphenyl-4-(4-(triphenylen-2-yl)styryl)aniline)(TSTA)
将E(1.0g,2.20mmol)或E1与4-二苯胺基苯甲醛(4-(N,N-diphenylamino)benzaldehyde)(0.72g,2.64mmol)置于双颈瓶中,抽真空通入氮气后,加入无水THF(20mL);在冰浴下,将溶于THF(20ml)的叔丁醇钾(0.49g,4.40mmole)缓缓加入混合,于0℃反应15分钟,反应结束后,减压浓缩去除溶剂,最后进行升华,温度为260℃,得黄色固体1.04g,产率82%。
1H NMR(400MHz,CD2Cl2):δ8.93(d,J=1.6Hz,1H),8.81-8.69(m,5H),7.98(dd,J=8.4,J=1.6Hz,1H),7.86(d,J=8.0Hz,2H),7.73-7.68(m,6H),7.46(d,J=8.4Hz,2H),7.31-7.27(m,4H),7.22-7.04(m,10H).
13C NMR(100MHz,CD2Cl2):δ147.9,140.0,139.7,137.5,131.8,130.5,130.4,130.1,130.0,129.7,129.3,128.8,127.9,127.8,127.3,126.7,126.5,125.0,124.4,123.8,123.5,121.7.
HRMS(m/z):[M+]calcd.for C44H31N,573.2457;found,573.2460
Anal.calcd for C44H31N:C,92.11;H,5.45;N,2.44;found:C,91.94;H,5.46;N,2.45
(E)-N-苯基-N-(4-(4-(2-联三伸苯基)苯乙烯基)苯基)萘基-1-胺((E)-N-phenyl-N-(4-(4-(triphenylen-2-yl)styryl)phenyl)naphthalen-1-amine)(TSNA)
将E(1.06g,2.33mmol)或E1与F(0.91g,2.80mmol)置于双颈瓶中,抽真空通入氮气后,加入无水THF(20mL);在冰浴下,将溶于THF(20ml)的叔丁醇钾(523mg,4.66mmole)缓缓加入混合,于0℃反应15分钟,反应结束后,减压浓缩去除溶剂,最后进行升华,温度为320℃,得黄色固体1.15g,产率79%。
1H NMR(400MHz,CDCl3):δ8.90(s,1H),8.79-8.66(m,5H),7.98-7.91(m,3H),7.85-7.80(m,3H),7.71-7.63(m,6H),7.55-7.48(m,2H),7.42-7.37(m,4H),7.27-6.99(m,9H).
13C NMR(100MHz,CDCl3):δ148.5,148.4,143.6,139.8,139.6,137.5,135.8,131.6,130.8,130.4,130.4,130.1,129.9,129.5,129.2,128.8,128.7,127.8,127.7,127.2,127.1,126.8,126.6,126.4,126.2,124.4,124.3,123.7,122.8,122.6,121.6,121.5.
HRMS(m/z):[M+]calcd.for C48H33N,623.2613;found,623.2616
Anal.calcd for C48H33N:C,92.42;H,5.33;N,2.25;found:C,92.38;H,5.08;N,2.33
(E)-4-甲基-N-p-甲苯基-N-(4-(4-(2-联三伸苯基)苯乙烯基)苯基)苯胺((E)-4-Methyl-N-p-tolyl-N-(4-(4-(triphenylen-2-yl)styryl)phenyl)aniline)(TSMA)
将E(1.20g,2.64mmol)或E1与H(0.96g,3.17mmol)置于双颈瓶中,抽真空通入氮气后,加入无水THF(20mL);在冰浴下,将溶于THF(20ml)的叔丁醇钾(593mg,5.28mmole)缓缓加入混合,于0℃反应15分钟,反应结束后,减压浓缩去除溶剂,最后进行升华,温度为290℃,得黄色固体1.15g,产率82%。
1H NMR(400MHz,CD2Cl2):δ8.92(d,J=1.2Hz,1H),8.81-8.69(m,5H),7.97(d,J=8.4,J=1.6Hz,1H),7.85(d,J=8.4Hz,2H),7.73-7.66(m,6H),7.41(d,J=8.8Hz,2H),7.20-6.97(m,12H),2.33(s,6H).
13C NMR(100MHz,CD2Cl2):δ148.4,145.4,139.8,139.7,137.5,133.4,130.7,130.4,130.4,130.3,130.1,129.9,129.2,128.9,127.8,127.8,127.7,127.6,127.2,126.4,126.1,125.2,124.3,123.7,122.4,121.7,20.9.
HRMS(m/z):[M+]calcd.for C46H35N,601.2770;found,601.2767
Anal.calcd for C46H35N:C,91.81;H,5.86;N,2.33;found:C,91.67;H,5.92;N,2.32
联三伸苯基衍生物的发旋光性质
请参照表一,本发明的联三伸苯基衍生物的放射波长为384至462nm,因此联三伸苯基化合物可发射蓝光,其波长半高宽(FWHM)为50-59nm。
表一、联三伸苯基衍生物的发旋光性质
N.D.:无侦测到。
有机发光二极管结构
此外,请参照图1,为示意图显示具有联三伸苯基衍生物的有机发光二极管结构的一实施例。有机发光二极管结构具有设置于阳极1及阴极2的间包含化合物的发光层3。发光层3系将发光材料掺杂至主体发光材料中所构成。有机发光二极管结构还包括从阳极1上方依序形成的电洞注入层7、电洞传输层4、电子阻挡层9、发光层3、电洞阻挡层6、电子传输层5及电子注入层8。其中,各层的实际厚度与图中所显示的尺寸并无关系。其中,有机发光二极管的电子阻挡层9、电洞阻挡层6及电子注入层8为选择性包含。
在一实施例中,本发明的联三伸苯基衍生物可为发光层的一主体发光材料或其掺杂物。
掺杂的有机发光二极管结构
在一掺杂物的有机发光二极管结构,其中以ITO做为基板,测试的阴极材料包括LiF/Al;DMPPP则用以作为发光层的主体材料并掺杂5%的本发明的化合物;测试的电洞传输层TCTA(4,4’,4”-tri(N-carbazolyl)triphenylamine);测试的电子传输层BCP(2,9-dimethyl-4,7-diphenyl-[1,10]phenanthroline);掺杂发光材料的对照组为BCzVBi(4,4’-(Bis(9-ethyl-3-carbazovinylene)-1,1’-biphenyl)。
例示测试装置的个别详细架构及其厚度(单位为nm)如下列,所得结果如表二:
装置A:TCTA(50)/DMPPP:TSCz(5%)(40)/BCP(30)/LiF(1)/Al(100)
装置B:TCTA(50)/DMPPP:TSTA(5%)(40)/BCP(30)/LiF(1)/Al(100)
装置C:TCTA(50)/DMPPP:TSNA(5%)(40)/BCP(30)/LiF(1)/Al(100)
装置D:TCTA(50)/DMPPP:TSMA(5%)(40)/BCP(30)/LiF(1)/Al(100)
装置E:TCTA(50)/DMPPP:BCzVBi(5%)(40)/BCP(30)/LiF(1)/Al(100)
表二、掺杂联三伸苯基衍生物的有机发光二极管效能表
其中分别包含掺杂发光物TSTA、TSNA及TSMA的装置B、C及D在发光效率、电流效率、最大亮度、半高全宽、光色及组件寿命等性质方面都具有良好性能。
综合上述,本发明的联三伸苯基衍生物可放出蓝光,其可作为主体发光材料及掺杂物,并可运用于有机发光二极管装置中,以达成高效率、低操作电压、高亮度及长组件操作寿命等优势。
以上所述的实施例仅是为说明本发明的技术思想及特点,其目的在使熟习此项技艺的人士能够了解本发明的内容并据以实施,当不能以之限定本发明的专利范围,即大凡依本发明所揭示的精神所作的均等变化或修饰,仍应涵盖在本发明的专利范围内。
Claims (17)
3.如权利要求1所述的联三伸苯基衍生物,其特征在于,其中R1及R2的至少其一为苯基。
7.如权利要求1所述的联三伸苯基衍生物,其特征在于,系选自由(E)-2-(4-苯乙烯基苯基)联三伸苯((E)-2-(4-Styrylphenyl)triphenylene,TSP)、2-(4-(2,2-二苯基乙烯基)苯基)联三伸苯(2-(4-(2,2-Diphenylvinyl)phenyl)triphenylene,TSDP)、2-(4-(1,2,2-三苯基乙烯基)苯基)联三伸苯(2-(4-(1,2,2-Triphenylvinyl)phenyl)triphenylene,TSTP)、(E)-9-乙基-3-(4-(2-联三伸苯基)苯乙烯基)-9H-咔唑((E)-9-Ethyl-3-(4-(triphenylen-2-yl)styryl)-9H-carbazole,TSCz)、(E)-N,N-二苯基-4-(4-(2-联三伸苯基)苯乙烯基)苯胺((E)-N,N-diphenyl-4-(4-(triphenylen-2-yl)styryl)aniline,TSTA)、(E)-N-苯基-N-(4-(4-(2-联三伸苯基)苯乙烯基)苯基)萘基-1-胺((E)-N-phenyl-N-(4-(4-(triphenylen-2-yl)styryl)phenyl)naphthalen-1-amine,TSNA)及(E)-4-甲基-N-p-甲苯基-N-(4-(4-(2-联三伸苯基)苯乙烯基)苯基)苯胺((E)-4-Methyl-N-p-tolyl-N-(4-(4-(triphenylen-2-yl)styry l)phenyl)aniline,TSMA)所组成的群组。
10.如权利要求8所述的有机发光二极管,其特征在于,其中R1及R2的至少其一为苯基。
11.如权利要求8所述的有机发光二极管,其特征在于,其中该联三伸苯基衍生物具有下列化学式(3):
其中R18-R22系选自由氢、卤素、氰基、三氟甲烷基、胺基、C1-C10烷基、C2-C10烯基、C2-C10炔基、C3-C20环烷基、C3-C20环烯基、C1-C20杂环烷基、C1-C20杂环烯基、芳基及杂芳基所组成的群组。
14.如权利要求8所述的有机发光二极管,其特征在于,其中该联三伸苯基衍生物系选自由(E)-2-(4-苯乙烯基苯基)联三伸苯((E)-2-(4-Styrylphenyl)triphenylene,TSP)、2-(4-(2,2-二苯基乙烯基)苯基)联三伸苯(2-(4-(2,2-Diphenylvinyl)phenyl)triphenylene,TSDP)、2-(4-(1,2,2-三苯基乙烯基)苯基)联三伸苯(2-(4-(1,2,2-Triphenylvinyl)phenyl)triphenylene,TSTP)、(E)-9-乙基-3-(4-(2-联三伸苯基)苯乙烯基)-9H-咔唑((E)-9-Ethyl-3-(4-(triphenylen-2-yl)styryl)-9H-carbazole,TSCz)、(E)-N,N-二苯基-4-(4-(2-联三伸苯基)苯乙烯基)苯胺((E)-N,N-diphenyl-4-(4-(triphenylen-2-yl)styryl)aniline,TSTA)、(E)-N-苯基-N-(4-(4-(2-联三伸苯基)苯乙烯基)苯基)萘基-1-胺((E)-N-phenyl-N-(4-(4-(triphenylen-2-yl)styryl)phenyl)naphthalen-1-amine,TSNA)及(E)-4-甲基-N-p-甲苯基-N-(4-(4-(2-联三伸苯基)苯乙烯基)苯基)苯胺((E)-4-Methyl-N-p-tolyl-N-(4-(4-(triphenylen-2-yl)styryl)phenyl)aniline,TSMA)所组成的群组。
15.如权利要求8所述的有机发光二极管,其特征在于,其中该联三伸苯基衍生物为一主体发光材料。
16.如权利要求8所述的有机发光二极管,其特征在于,其中该联三伸苯基衍生物为一掺杂物。
17.如权利要求8所述的有机发光二极管,其特征在于,其中该有机发光二极管为一蓝色发光二极管。
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US9705092B2 (en) | 2011-08-05 | 2017-07-11 | Universal Display Corporation | Phosphorescent organic light emitting devices combined with hole transport material having high operating stability |
CN108550533A (zh) * | 2018-04-23 | 2018-09-18 | 吉林师范大学 | 一种基于DMPPP的荧光染料掺杂的深蓝色OLEDs的检测方法 |
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010050779A1 (en) * | 2008-10-30 | 2010-05-06 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
TW201127782A (en) * | 2010-02-03 | 2011-08-16 | Nat Univ Tsing Hua | Triphenylene based aromatic compounds and OLEDs utilizing the same |
CN102241620A (zh) * | 2010-05-14 | 2011-11-16 | 国立清华大学 | 含苯并[9,10]菲基的芳香族化合物及利用其的有机发光二极管 |
Family Cites Families (6)
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KR101156423B1 (ko) * | 2005-04-30 | 2012-06-18 | 삼성모바일디스플레이주식회사 | 아미노스티릴 화합물, 이의 제조 방법 및 이를 구비한 유기발광 소자 |
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US8288015B2 (en) * | 2010-04-18 | 2012-10-16 | National Tsing Hua University | Triphenylene based aromatic compounds and OLEDs utilizing the same |
JP2011225501A (ja) * | 2010-04-22 | 2011-11-10 | Canon Inc | 新規m−ターフェニル化合物及びこれを有する有機発光素子 |
-
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010050779A1 (en) * | 2008-10-30 | 2010-05-06 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
TW201127782A (en) * | 2010-02-03 | 2011-08-16 | Nat Univ Tsing Hua | Triphenylene based aromatic compounds and OLEDs utilizing the same |
CN102241620A (zh) * | 2010-05-14 | 2011-11-16 | 国立清华大学 | 含苯并[9,10]菲基的芳香族化合物及利用其的有机发光二极管 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9705092B2 (en) | 2011-08-05 | 2017-07-11 | Universal Display Corporation | Phosphorescent organic light emitting devices combined with hole transport material having high operating stability |
CN104860884A (zh) * | 2015-05-19 | 2015-08-26 | 苏州大学 | 类三苯基乙烯衍生物及其用途 |
CN104860884B (zh) * | 2015-05-19 | 2017-06-20 | 苏州大学 | 类三苯基乙烯衍生物及其用途 |
CN108550533A (zh) * | 2018-04-23 | 2018-09-18 | 吉林师范大学 | 一种基于DMPPP的荧光染料掺杂的深蓝色OLEDs的检测方法 |
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