WO2015141608A1 - 電子輸送材料およびこれを用いた有機電界発光素子 - Google Patents
電子輸送材料およびこれを用いた有機電界発光素子 Download PDFInfo
- Publication number
- WO2015141608A1 WO2015141608A1 PCT/JP2015/057617 JP2015057617W WO2015141608A1 WO 2015141608 A1 WO2015141608 A1 WO 2015141608A1 JP 2015057617 W JP2015057617 W JP 2015057617W WO 2015141608 A1 WO2015141608 A1 WO 2015141608A1
- Authority
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- WIPO (PCT)
- Prior art keywords
- compound
- formula
- group
- cyanopyridin
- phenyl
- Prior art date
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- 0 C*(**C1=**)*C1=C=C Chemical compound C*(**C1=**)*C1=C=C 0.000 description 6
- FDUFXABWHVFLQC-UHFFFAOYSA-N Br[IH]c(c1c2cccc1)c(cccc1)c1c2[IH]Br Chemical compound Br[IH]c(c1c2cccc1)c(cccc1)c1c2[IH]Br FDUFXABWHVFLQC-UHFFFAOYSA-N 0.000 description 1
- DWLHTEUYNLCHEZ-TWMGOJRQSA-N C/C(/C#N)=C\C(\c(cc1)ccc1-c1c(cc2[o]c3ccccc3c2c2)c2c(-c(cc2)ccc2C2=CC(C#N)=C[N-]C2)c2c1cccc2)=C/N Chemical compound C/C(/C#N)=C\C(\c(cc1)ccc1-c1c(cc2[o]c3ccccc3c2c2)c2c(-c(cc2)ccc2C2=CC(C#N)=C[N-]C2)c2c1cccc2)=C/N DWLHTEUYNLCHEZ-TWMGOJRQSA-N 0.000 description 1
- OWFRQQIVESQNEE-RGHXKVHDSA-N C=C(/C=C(\C=C/N)/c1cccc(-c(cc2)cc3c2c(c(cccc2)c2cc2)c2[n]3-c2ccccc2)n1)C#N Chemical compound C=C(/C=C(\C=C/N)/c1cccc(-c(cc2)cc3c2c(c(cccc2)c2cc2)c2[n]3-c2ccccc2)n1)C#N OWFRQQIVESQNEE-RGHXKVHDSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C Chemical compound CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- YOBWHZZWEHKYIK-UHFFFAOYSA-N CC1(C)OB(c2ccc(cc(cc3)-c4c(cccc5)c5c(-c5ccc(C)cc5)c5ccccc45)c3c2)OC1(C)C Chemical compound CC1(C)OB(c2ccc(cc(cc3)-c4c(cccc5)c5c(-c5ccc(C)cc5)c5ccccc45)c3c2)OC1(C)C YOBWHZZWEHKYIK-UHFFFAOYSA-N 0.000 description 1
- BOIKCRIMIQAFQJ-UHFFFAOYSA-N CC1(C)OB(c2cncc(C#N)c2)OC1(C)C Chemical compound CC1(C)OB(c2cncc(C#N)c2)OC1(C)C BOIKCRIMIQAFQJ-UHFFFAOYSA-N 0.000 description 1
- UCFSYHMCKWNKAH-UHFFFAOYSA-N CC1(C)OBOC1(C)C Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 1
- SWLYVTSQYRPTHW-UHFFFAOYSA-N CC1(C)c(cc(cc2)-c(cc3)cc(cc4)c3cc4-c3cc(-c4ccc-5c6c4cccc6-c4ccccc-54)ccc3)c2-c2ccccc12 Chemical compound CC1(C)c(cc(cc2)-c(cc3)cc(cc4)c3cc4-c3cc(-c4ccc-5c6c4cccc6-c4ccccc-54)ccc3)c2-c2ccccc12 SWLYVTSQYRPTHW-UHFFFAOYSA-N 0.000 description 1
- FAPBMQHYXHNYGZ-UHFFFAOYSA-N CCCc(ccc1c(cc2C(c3c4)(c5ccccc5)c5ccccc5)-c5ccccc5)cc1c2-c3ccc4-c1cc(C#N)cnc1 Chemical compound CCCc(ccc1c(cc2C(c3c4)(c5ccccc5)c5ccccc5)-c5ccccc5)cc1c2-c3ccc4-c1cc(C#N)cnc1 FAPBMQHYXHNYGZ-UHFFFAOYSA-N 0.000 description 1
- NCCZFLCNGKFPFP-UHFFFAOYSA-N CCCc1c(c(-c(c(C23c4ccccc4-c4ccccc24)c2)ccc2-c(cc2)ccc2C2=CNCC(C#N)=C2)c3cc2-c(cc3)ccc3-c3cncc(C#N)c3)c2ccc1 Chemical compound CCCc1c(c(-c(c(C23c4ccccc4-c4ccccc24)c2)ccc2-c(cc2)ccc2C2=CNCC(C#N)=C2)c3cc2-c(cc3)ccc3-c3cncc(C#N)c3)c2ccc1 NCCZFLCNGKFPFP-UHFFFAOYSA-N 0.000 description 1
- ZJONNTFPULRNLS-UHFFFAOYSA-N CCCc1c(c(-c(cc2)c(C34c5ccccc5-c5ccccc35)cc2-c2ccc(-c3cc(C#N)ccn3)nc2)c4cc2-c(cc3)cnc3-c3nccc(C#N)c3)c2ccc1 Chemical compound CCCc1c(c(-c(cc2)c(C34c5ccccc5-c5ccccc35)cc2-c2ccc(-c3cc(C#N)ccn3)nc2)c4cc2-c(cc3)cnc3-c3nccc(C#N)c3)c2ccc1 ZJONNTFPULRNLS-UHFFFAOYSA-N 0.000 description 1
- UJPDAFJINOFXEQ-UHFFFAOYSA-N CCCc1c(c(-c(cc2)c(C34c5ccccc5-c5ccccc35)cc2-c2nc(-c3cncc(C#N)c3)ccc2)c4cc2-c3cccc(-c4cc(C#N)cnc4)n3)c2ccc1 Chemical compound CCCc1c(c(-c(cc2)c(C34c5ccccc5-c5ccccc35)cc2-c2nc(-c3cncc(C#N)c3)ccc2)c4cc2-c3cccc(-c4cc(C#N)cnc4)n3)c2ccc1 UJPDAFJINOFXEQ-UHFFFAOYSA-N 0.000 description 1
- CBOKIZZSGZOWIJ-UHFFFAOYSA-N CCCc1cc(c(-c(c(C2(c3ccccc3)c3ccccc3)c3)ccc3-c(cc3)ccc3-c3cc(C#N)cnc3)c2cc2)c2cc1 Chemical compound CCCc1cc(c(-c(c(C2(c3ccccc3)c3ccccc3)c3)ccc3-c(cc3)ccc3-c3cc(C#N)cnc3)c2cc2)c2cc1 CBOKIZZSGZOWIJ-UHFFFAOYSA-N 0.000 description 1
- WRXZKXOSOQHCQF-UHFFFAOYSA-N CCCc1cc2c3c(c(cccc4)c4c(-c4cc(-c5cncc(C#N)c5)ccc4)c4)c4[s]c3cc(-c3cccc(-c4cc(C#N)cnc4)c3)c2cc1 Chemical compound CCCc1cc2c3c(c(cccc4)c4c(-c4cc(-c5cncc(C#N)c5)ccc4)c4)c4[s]c3cc(-c3cccc(-c4cc(C#N)cnc4)c3)c2cc1 WRXZKXOSOQHCQF-UHFFFAOYSA-N 0.000 description 1
- MXZKHBKVIJMSHZ-UHFFFAOYSA-N Cc1c(cccc2)c2c(C)c2cc(cccc3)c3cc12 Chemical compound Cc1c(cccc2)c2c(C)c2cc(cccc3)c3cc12 MXZKHBKVIJMSHZ-UHFFFAOYSA-N 0.000 description 1
- GJAURBKCSAWSEA-UHFFFAOYSA-N Cc1cc(C)c(B(c(c2c3cccc2)ccc3-c(cc2)c(cccc3)c3c2-[n]2c(cccc3)c3c3c2cccc3)c2c(C)cc(C)cc2C)c(C)c1 Chemical compound Cc1cc(C)c(B(c(c2c3cccc2)ccc3-c(cc2)c(cccc3)c3c2-[n]2c(cccc3)c3c3c2cccc3)c2c(C)cc(C)cc2C)c(C)c1 GJAURBKCSAWSEA-UHFFFAOYSA-N 0.000 description 1
- LTQDLLBLJFXYQB-UHFFFAOYSA-N N#CC(C1)=CN=CC1c(cc1)ccc1-c1cc([s]c2c3c(cccc4)c4c(-c(cc4)ccc4-c4cc(C#N)cnc4)c2)c3c2c1cccc2 Chemical compound N#CC(C1)=CN=CC1c(cc1)ccc1-c1cc([s]c2c3c(cccc4)c4c(-c(cc4)ccc4-c4cc(C#N)cnc4)c2)c3c2c1cccc2 LTQDLLBLJFXYQB-UHFFFAOYSA-N 0.000 description 1
- FTFSTZJEUWIEBO-UHFFFAOYSA-O N#CC(C1)[NH2+]C=CC1c1cc([s]c2c3c(cccc4)c4c(-c4cc(C#N)ncc4)c2)c3c2c1cccc2 Chemical compound N#CC(C1)[NH2+]C=CC1c1cc([s]c2c3c(cccc4)c4c(-c4cc(C#N)ncc4)c2)c3c2c1cccc2 FTFSTZJEUWIEBO-UHFFFAOYSA-O 0.000 description 1
- TXFDLEJDBJJUIY-UHFFFAOYSA-N N#CC(C=C1)[N-]C=C1c1cc(-c2c(cccc3)c3c(-c3cc(-c4ccc(C#N)nc4)ccc3)c3c2cccc3)ccc1 Chemical compound N#CC(C=C1)[N-]C=C1c1cc(-c2c(cccc3)c3c(-c3cc(-c4ccc(C#N)nc4)ccc3)c3c2cccc3)ccc1 TXFDLEJDBJJUIY-UHFFFAOYSA-N 0.000 description 1
- JDIUHFMYLAHSKA-UHFFFAOYSA-N N#CC1=CC(c2cc(-c3c(cc4[o]c5ccccc5c4c4)c4c(-c4cc(-c5cncc(C#N)c5)ccc4)c4c3cccc4)ccc2)=C[N-]C1 Chemical compound N#CC1=CC(c2cc(-c3c(cc4[o]c5ccccc5c4c4)c4c(-c4cc(-c5cncc(C#N)c5)ccc4)c4c3cccc4)ccc2)=C[N-]C1 JDIUHFMYLAHSKA-UHFFFAOYSA-N 0.000 description 1
- SHNFQTOFBLJVQU-UHFFFAOYSA-N N#CC1=CC(c2cc(-c3c(cccc4)c4c(-c4cc(-c5cncc(C#N)c5)ccc4)c4c3cccc4)ccc2)=C[N-]C1 Chemical compound N#CC1=CC(c2cc(-c3c(cccc4)c4c(-c4cc(-c5cncc(C#N)c5)ccc4)c4c3cccc4)ccc2)=C[N-]C1 SHNFQTOFBLJVQU-UHFFFAOYSA-N 0.000 description 1
- XSKMXIXSPWUXDZ-UHFFFAOYSA-N N#CC1=CC(c2cc([s]c3cc(-c4ccccc4)ccc33)c3c3ccccc23)NC=C1 Chemical compound N#CC1=CC(c2cc([s]c3cc(-c4ccccc4)ccc33)c3c3ccccc23)NC=C1 XSKMXIXSPWUXDZ-UHFFFAOYSA-N 0.000 description 1
- GXELBDKUPCUEKU-UHFFFAOYSA-N N#CC1=CC(c2cccc(-c(cc3)cc4c3-c3c(cccc5)c5ccc3C4(c3ccccc3)c3ccccc3)c2)=CNC1 Chemical compound N#CC1=CC(c2cccc(-c(cc3)cc4c3-c3c(cccc5)c5ccc3C4(c3ccccc3)c3ccccc3)c2)=CNC1 GXELBDKUPCUEKU-UHFFFAOYSA-N 0.000 description 1
- WJNSTVQSOPBYHZ-UHFFFAOYSA-N N#CC1=CC(c2cccc(-c(cc3C45c6ccccc6-c6ccccc46)ccc3-c(cc3)c5cc3-c3ccccc3)c2)=CCN1 Chemical compound N#CC1=CC(c2cccc(-c(cc3C45c6ccccc6-c6ccccc46)ccc3-c(cc3)c5cc3-c3ccccc3)c2)=CCN1 WJNSTVQSOPBYHZ-UHFFFAOYSA-N 0.000 description 1
- PTLNVVPEGATTCQ-UHFFFAOYSA-N N#CC1=CC(c2nc(-c(c3c4cccc3)c(cc3[o]c(cccc5)c5c3c3)c3c4-c3nc(-c4cc(C#N)cnc4)ccc3)ccc2)=C[N-]C1 Chemical compound N#CC1=CC(c2nc(-c(c3c4cccc3)c(cc3[o]c(cccc5)c5c3c3)c3c4-c3nc(-c4cc(C#N)cnc4)ccc3)ccc2)=C[N-]C1 PTLNVVPEGATTCQ-UHFFFAOYSA-N 0.000 description 1
- ZSNIXRVPPOKEQN-UHFFFAOYSA-N N#CC1=[N]=CC(c2cc(-c3c(cccc4)c4c(-c4cc(-c5cc(C#N)ncc5)ccc4)c4c3cccc4)ccc2)=C1 Chemical compound N#CC1=[N]=CC(c2cc(-c3c(cccc4)c4c(-c4cc(-c5cc(C#N)ncc5)ccc4)c4c3cccc4)ccc2)=C1 ZSNIXRVPPOKEQN-UHFFFAOYSA-N 0.000 description 1
- OOAVUYYOMYPWDU-UHFFFAOYSA-N N#CC1C2NCC(c3cccc(-c4cc([s]c5c6c(cccc7)c7c(-c7cccc(-c8cc(C#N)cnc8)n7)c5)c6c5c4cccc5)n3)=CC12 Chemical compound N#CC1C2NCC(c3cccc(-c4cc([s]c5c6c(cccc7)c7c(-c7cccc(-c8cc(C#N)cnc8)n7)c5)c6c5c4cccc5)n3)=CC12 OOAVUYYOMYPWDU-UHFFFAOYSA-N 0.000 description 1
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- RCFCFKFXSXVTJW-UHFFFAOYSA-N N#CC1NC=CC(c2cc(C3(c4ccccc4-c4ccccc34)c3c-4ccc(-c5cc(C#N)ncc5)c3)c-4c3c2cccc3)=C1 Chemical compound N#CC1NC=CC(c2cc(C3(c4ccccc4-c4ccccc34)c3c-4ccc(-c5cc(C#N)ncc5)c3)c-4c3c2cccc3)=C1 RCFCFKFXSXVTJW-UHFFFAOYSA-N 0.000 description 1
- KHGSMSWYNFXSLS-UHFFFAOYSA-N N#CC1NC=CC(c2cccc(-c(cc3)cc(C45c6ccccc6-c6c4cccc6)c3-c3c5cc(C4NC(c5cc(C#N)ncc5)=CC=C4)c4ccccc34)n2)=C1 Chemical compound N#CC1NC=CC(c2cccc(-c(cc3)cc(C45c6ccccc6-c6c4cccc6)c3-c3c5cc(C4NC(c5cc(C#N)ncc5)=CC=C4)c4ccccc34)n2)=C1 KHGSMSWYNFXSLS-UHFFFAOYSA-N 0.000 description 1
- LVNRALHEDBOFCB-UHFFFAOYSA-N N#CC1NC=CC(c2cccc(-c(cc3)cc(C45c6ccccc6-c6ccccc46)c3-c3c5cc(-c4cccc(-c5cc(C#N)ncc5)c4)c4ccccc34)c2)=C1 Chemical compound N#CC1NC=CC(c2cccc(-c(cc3)cc(C45c6ccccc6-c6ccccc46)c3-c3c5cc(-c4cccc(-c5cc(C#N)ncc5)c4)c4ccccc34)c2)=C1 LVNRALHEDBOFCB-UHFFFAOYSA-N 0.000 description 1
- WUKRXBIFTGOSNY-UHFFFAOYSA-O N#CC1[NH2+]C=CC(c(cc2)ccc2-c2cc([s]c3c4c(CCC=C5)c5c(-c(cc5)ccc5-c5cc(C#N)ncc5)c3)c4c3c2cccc3)=C1 Chemical compound N#CC1[NH2+]C=CC(c(cc2)ccc2-c2cc([s]c3c4c(CCC=C5)c5c(-c(cc5)ccc5-c5cc(C#N)ncc5)c3)c4c3c2cccc3)=C1 WUKRXBIFTGOSNY-UHFFFAOYSA-O 0.000 description 1
- DQDFMYKGAZHQKT-UHFFFAOYSA-N N#Cc(cc1)ccc1-c1c(ccc(-c2ccccc2)c2)c2c(-c(cc2)ccc2C#N)c2ccccc12 Chemical compound N#Cc(cc1)ccc1-c1c(ccc(-c2ccccc2)c2)c2c(-c(cc2)ccc2C#N)c2ccccc12 DQDFMYKGAZHQKT-UHFFFAOYSA-N 0.000 description 1
- ZPRAKRZZVJYQLL-UHFFFAOYSA-N N#Cc(ccnc1)c1-c1cccc(-c2c(cccc3)c3c(-c3cccc(C4=C[N-]CC=C4C#N)c3)c3c2cccc3)c1 Chemical compound N#Cc(ccnc1)c1-c1cccc(-c2c(cccc3)c3c(-c3cccc(C4=C[N-]CC=C4C#N)c3)c3c2cccc3)c1 ZPRAKRZZVJYQLL-UHFFFAOYSA-N 0.000 description 1
- YPNAXCAFCLORHX-UHFFFAOYSA-N N#Cc(nc1)ccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c(cc2)cnc2C#N)nc(-c(cc2)ccc2-c(cc2)cnc2C#N)n1 Chemical compound N#Cc(nc1)ccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c(cc2)cnc2C#N)nc(-c(cc2)ccc2-c(cc2)cnc2C#N)n1 YPNAXCAFCLORHX-UHFFFAOYSA-N 0.000 description 1
- ATRRAUAHGCWKRK-UHFFFAOYSA-N N#Cc1c(-c2cc(-c3c(cccc4)c4c(-c4cc(-c(nccc5)c5C#N)ccc4)c4c3cccc4)ccc2)nccc1 Chemical compound N#Cc1c(-c2cc(-c3c(cccc4)c4c(-c4cc(-c(nccc5)c5C#N)ccc4)c4c3cccc4)ccc2)nccc1 ATRRAUAHGCWKRK-UHFFFAOYSA-N 0.000 description 1
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- RCSDTOYNQVXHRG-UHFFFAOYSA-N N#Cc1cc(-c(cc2)ccc2-c(cc2)cc(C3(c4ccccc4)c4ccccc4)c2-c2c3ccc3ccccc23)ncc1 Chemical compound N#Cc1cc(-c(cc2)ccc2-c(cc2)cc(C3(c4ccccc4)c4ccccc4)c2-c2c3ccc3ccccc23)ncc1 RCSDTOYNQVXHRG-UHFFFAOYSA-N 0.000 description 1
- PQULLIFAKUWDPT-UHFFFAOYSA-N N#Cc1cc(-c(cc2)ccc2-c(cc2)cc(c3c4)c2[o]c3ccc4-c2ccccc2)ccn1 Chemical compound N#Cc1cc(-c(cc2)ccc2-c(cc2)cc(c3c4)c2[o]c3ccc4-c2ccccc2)ccn1 PQULLIFAKUWDPT-UHFFFAOYSA-N 0.000 description 1
- NRZHXDMNIXXQCB-UHFFFAOYSA-N N#Cc1cc(-c(cc2)ccc2-c(cc2)cc(c3c4)c2[o]c3ccc4-c2ccccc2)ncc1 Chemical compound N#Cc1cc(-c(cc2)ccc2-c(cc2)cc(c3c4)c2[o]c3ccc4-c2ccccc2)ncc1 NRZHXDMNIXXQCB-UHFFFAOYSA-N 0.000 description 1
- ZUCNNHFNZSFJCO-UHFFFAOYSA-N N#Cc1cc(-c(cc2)ccc2-c(cc2C34c5ccccc5-c5ccccc35)ccc2-c(cc2)c4cc2-c2ccccc2)ncc1 Chemical compound N#Cc1cc(-c(cc2)ccc2-c(cc2C34c5ccccc5-c5ccccc35)ccc2-c(cc2)c4cc2-c2ccccc2)ncc1 ZUCNNHFNZSFJCO-UHFFFAOYSA-N 0.000 description 1
- RINTXDWURMKSFH-UHFFFAOYSA-N N#Cc1cc(-c(cc2)ccc2-c2c(cccc3)c3c(-c(cc3)ccc3-c3cc(C#N)ncc3)c3c2cc(c2ccccc2[o]2)c2c3)ccn1 Chemical compound N#Cc1cc(-c(cc2)ccc2-c2c(cccc3)c3c(-c(cc3)ccc3-c3cc(C#N)ncc3)c3c2cc(c2ccccc2[o]2)c2c3)ccn1 RINTXDWURMKSFH-UHFFFAOYSA-N 0.000 description 1
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- GEOYLMAESICDMC-UHFFFAOYSA-N N#Cc1nccc(-c(cc2)ccc2-c(cc2)cc3c2c(c(cccc2)c2cc2)c2[n]3-c2ccccc2)c1 Chemical compound N#Cc1nccc(-c(cc2)ccc2-c(cc2)cc3c2c(c(cccc2)c2cc2)c2[n]3-c2ccccc2)c1 GEOYLMAESICDMC-UHFFFAOYSA-N 0.000 description 1
- BCCJXEAVIGSIBQ-UHFFFAOYSA-N N#Cc1nccc(-c(cc2)ccc2-c(cc2C3(c4ccccc4)c4ccccc4)ccc2-c2c3ccc3ccccc23)c1 Chemical compound N#Cc1nccc(-c(cc2)ccc2-c(cc2C3(c4ccccc4)c4ccccc4)ccc2-c2c3ccc3ccccc23)c1 BCCJXEAVIGSIBQ-UHFFFAOYSA-N 0.000 description 1
- PGZWZGVKTZXFFK-UHFFFAOYSA-N N#Cc1nccc(-c(cc2)ccc2-c(cc2C34c5ccccc5-c5c3cccc5)ccc2-c(cc2)c4cc2-c2ccccc2)c1 Chemical compound N#Cc1nccc(-c(cc2)ccc2-c(cc2C34c5ccccc5-c5c3cccc5)ccc2-c(cc2)c4cc2-c2ccccc2)c1 PGZWZGVKTZXFFK-UHFFFAOYSA-N 0.000 description 1
- QGDUPYCVZPLZMT-UHFFFAOYSA-N N#Cc1nccc(-c(cc2)ccc2-c2cc([s]c3c4cccc3)c4c3c2cccc3)c1 Chemical compound N#Cc1nccc(-c(cc2)ccc2-c2cc([s]c3c4cccc3)c4c3c2cccc3)c1 QGDUPYCVZPLZMT-UHFFFAOYSA-N 0.000 description 1
- NDZXLDBYFWCNAH-UHFFFAOYSA-N N#Cc1nccc(-c(cc2C3(c4ccccc4)c4ccccc4)ccc2-c2c3cc(-c3ccccc3)c3ccccc23)c1 Chemical compound N#Cc1nccc(-c(cc2C3(c4ccccc4)c4ccccc4)ccc2-c2c3cc(-c3ccccc3)c3ccccc23)c1 NDZXLDBYFWCNAH-UHFFFAOYSA-N 0.000 description 1
- GTKPBCVHYHXMDH-UHFFFAOYSA-N N#Cc1nccc(-c2cc(-c(cc3)cc(c4c5)c3[o]c4ccc5-c3ccccc3)ccc2)c1 Chemical compound N#Cc1nccc(-c2cc(-c(cc3)cc(c4c5)c3[o]c4ccc5-c3ccccc3)ccc2)c1 GTKPBCVHYHXMDH-UHFFFAOYSA-N 0.000 description 1
- FUZWLNXSPKPTHI-UHFFFAOYSA-N N#Cc1nccc(-c2cc(-c(cc3C4(c5ccccc5)c5ccccc5)ccc3-c3c4ccc4c3cccc4)ccc2)c1 Chemical compound N#Cc1nccc(-c2cc(-c(cc3C4(c5ccccc5)c5ccccc5)ccc3-c3c4ccc4c3cccc4)ccc2)c1 FUZWLNXSPKPTHI-UHFFFAOYSA-N 0.000 description 1
- YGONBKMUWRMRJI-UHFFFAOYSA-N N#Cc1nccc(-c2cc(-c3nc(-c4cc(-c5ccnc(C#N)c5)ccc4)nc(-c4cccc(-c5ccnc(C#N)c5)c4)n3)ccc2)c1 Chemical compound N#Cc1nccc(-c2cc(-c3nc(-c4cc(-c5ccnc(C#N)c5)ccc4)nc(-c4cccc(-c5ccnc(C#N)c5)c4)n3)ccc2)c1 YGONBKMUWRMRJI-UHFFFAOYSA-N 0.000 description 1
- PIYGLSGSCJXEGA-UHFFFAOYSA-N N#Cc1nccc(-c2cc([s]c3cc(-c4ccccc4)ccc33)c3c3ccccc23)c1 Chemical compound N#Cc1nccc(-c2cc([s]c3cc(-c4ccccc4)ccc33)c3c3ccccc23)c1 PIYGLSGSCJXEGA-UHFFFAOYSA-N 0.000 description 1
- JWWSAQKQGVUAHA-UHFFFAOYSA-N N#Cc1nccc(-c2cccc(-c(cc34)ccc3c(c(cccc3)c3cc3)c3[n]4-c3ccccc3)c2)c1 Chemical compound N#Cc1nccc(-c2cccc(-c(cc34)ccc3c(c(cccc3)c3cc3)c3[n]4-c3ccccc3)c2)c1 JWWSAQKQGVUAHA-UHFFFAOYSA-N 0.000 description 1
- AULIUTPPKIPFPC-UHFFFAOYSA-N N#Cc1nccc(-c2cccc(-c3cc([s]c4c5cccc4)c5c4c3cccc4)c2)c1 Chemical compound N#Cc1nccc(-c2cccc(-c3cc([s]c4c5cccc4)c5c4c3cccc4)c2)c1 AULIUTPPKIPFPC-UHFFFAOYSA-N 0.000 description 1
- UPHXALFTXFSHHV-UHFFFAOYSA-N N#Cc1nccc(-c2nc(-c(cc3)cc(c4c5)c3[o]c4ccc5-c3ccccc3)ccc2)c1 Chemical compound N#Cc1nccc(-c2nc(-c(cc3)cc(c4c5)c3[o]c4ccc5-c3ccccc3)ccc2)c1 UPHXALFTXFSHHV-UHFFFAOYSA-N 0.000 description 1
- UXWXPKRMGZGTFX-UHFFFAOYSA-N N#Cc1nccc(-c2nc(-c3nc(-c4nc(-c5cc(C#N)ncc5)ccc4)nc(-c4cccc(-c5cc(C#N)ncc5)n4)n3)ccc2)c1 Chemical compound N#Cc1nccc(-c2nc(-c3nc(-c4nc(-c5cc(C#N)ncc5)ccc4)nc(-c4cccc(-c5cc(C#N)ncc5)n4)n3)ccc2)c1 UXWXPKRMGZGTFX-UHFFFAOYSA-N 0.000 description 1
- VRIBXAAVQSCEBL-UHFFFAOYSA-N N#Cc1ncccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c2c(C#N)nccc2)nc(-c(cc2)ccc2-c2c(C#N)nccc2)n1 Chemical compound N#Cc1ncccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c2c(C#N)nccc2)nc(-c(cc2)ccc2-c2c(C#N)nccc2)n1 VRIBXAAVQSCEBL-UHFFFAOYSA-N 0.000 description 1
- MGRSWGHJEHXSKF-UHFFFAOYSA-N N#Cc1ncccc1-c1cccc(-c2c(cccc3)c3c(-c3cccc(C4=C(C#N)[N-]CC=C4)c3)c3c2cccc3)c1 Chemical compound N#Cc1ncccc1-c1cccc(-c2c(cccc3)c3c(-c3cccc(C4=C(C#N)[N-]CC=C4)c3)c3c2cccc3)c1 MGRSWGHJEHXSKF-UHFFFAOYSA-N 0.000 description 1
- NRPQGTWMWBDULM-UHFFFAOYSA-N [IH]=CCCc1c(cccc2)c2c(-c2ccccc2)c2c1cccc2 Chemical compound [IH]=CCCc1c(cccc2)c2c(-c2ccccc2)c2c1cccc2 NRPQGTWMWBDULM-UHFFFAOYSA-N 0.000 description 1
- VRLGIWMYVPKDOX-UHFFFAOYSA-N c(cc1)ccc1-c(ccc1c(c2c3cccc2)-c2nc(-c4cnccc4)ccc2)cc1c3-c1cccc(-c2cccnc2)n1 Chemical compound c(cc1)ccc1-c(ccc1c(c2c3cccc2)-c2nc(-c4cnccc4)ccc2)cc1c3-c1cccc(-c2cccnc2)n1 VRLGIWMYVPKDOX-UHFFFAOYSA-N 0.000 description 1
- VOOMCEYFGNFUQU-UHFFFAOYSA-N c(cc1)ccc1-c1cc2c(-c3ccc(-c4ncccc4)nc3)c3ccccc3c(-c(cc3)cnc3-c3ncccc3)c2cc1 Chemical compound c(cc1)ccc1-c1cc2c(-c3ccc(-c4ncccc4)nc3)c3ccccc3c(-c(cc3)cnc3-c3ncccc3)c2cc1 VOOMCEYFGNFUQU-UHFFFAOYSA-N 0.000 description 1
- RVOKDUHZRQKQNJ-UHFFFAOYSA-N c(cc12)ccc1-c1ccccc1C21c(cc(cc2)-c3nc(-c4ccncc4)ccc3)c2-c(cc2)c1cc2-c1cccc(-c2ccncc2)n1 Chemical compound c(cc12)ccc1-c1ccccc1C21c(cc(cc2)-c3nc(-c4ccncc4)ccc3)c2-c(cc2)c1cc2-c1cccc(-c2ccncc2)n1 RVOKDUHZRQKQNJ-UHFFFAOYSA-N 0.000 description 1
- WTCAIPIAIJHYOC-UHFFFAOYSA-N c1ccc2c(cc(cc3)-c4cccc(-c5ccncc5)n4)c3c(ccc(-c3nc(-c4ccncc4)ccc3)c3)c3c2c1 Chemical compound c1ccc2c(cc(cc3)-c4cccc(-c5ccncc5)n4)c3c(ccc(-c3nc(-c4ccncc4)ccc3)c3)c3c2c1 WTCAIPIAIJHYOC-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/00—Organic light-emitting devices
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- the present invention relates to a novel electron transport material having a cyanopyridyl group, an organic electroluminescence device using the electron transport material (hereinafter, sometimes abbreviated as an organic EL device or simply a device), and the like.
- the present invention has been made in view of the problems of such conventional techniques. It is an object of the present invention to provide an electron transport material that can achieve, in a well-balanced manner, improvements in characteristics required for an organic EL element, such as reduction in drive voltage, high efficiency, and long life. Furthermore, this invention makes it a subject to provide the organic EL element using this electron transport material.
- the present inventors have found that the use of an aromatic hydrocarbon or aromatic heterocycle substituted with a cyanopyridyl group via a linking group in the electron transport layer of the organic EL device reduces the driving voltage and increases the efficiency. It has been found that improvements in characteristics such as a longer life and longer life can be achieved in a balanced manner, and the present invention has been completed based on this finding.
- a compound represented by the following formula (1) Ar is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms.
- At least one hydrogen may be replaced by alkyl having 1 to 4 carbons; m is an integer of 1 to 4, and when m is 2, 3 or 4, the groups formed by the pyridine ring and L may be the same or different; L is a single bond or one selected from the group of divalent groups represented by the following formulas (L-1) and (L-2),
- X 1 to X 6 are independently ⁇ CR 1 — or ⁇ N—, and at least two of X 1 to X 6 are ⁇ CR 1 —, and X 1 to R 1 in two ⁇ CR 1 — of X 6 is a bond bonded to Ar or a pyridine ring, and R 1 in other ⁇ CR 1 — is hydrogen
- X 7 to X 14 are independently ⁇ CR 1 — or ⁇ N—, and at least two of X 7 to X 14 are ⁇ CR 1 —, and X 7 to R 1 in two ⁇ CR 1 — of X 14 is a bond
- Ar is represented by the following formulas (Ar1-1) to (Ar1-12), (Ar2-1) to (Ar2-21), (Ar3-1), (Ar3-2), and The compound according to item [1], which is one selected from the group of groups represented by (Ar4-1);
- Z is independently —O—, —S—, or one selected from the group of divalent groups represented by the following formulas (2) and (3), and at least one hydrogen of each group has 1 to 4 carbon atoms.
- R 1 is phenyl, naphthyl, biphenylyl, or terphenylyl.
- R 2 is independently methyl or phenyl, and R 2 is linked to each other to form a ring. May be.
- Ar is represented by the following formulas (Ar1-1) to (Ar1-7), (Ar2-1), (Ar2-3), (Ar2-6) to (Ar2-10), ( The compound according to item [1], which is one selected from the group of groups represented by Ar2-12), (Ar-2-21), (Ar3-1), and (Ar3-2); Formulas (Ar1-1) to (Ar1-7), (Ar2-1), (Ar2-3), (Ar2-6) to (Ar2-10), (Ar2-12), (Ar-2-21) , (Ar3-1), and (Ar3-2), Z is independently one selected from the group of divalent groups represented by the following formulas (2) and (3), At least one hydrogen of the group may be replaced by alkyl having 1 to 4 carbons or aryl having 6 to 18 carbons;
- R 1 is phenyl, naphthyl, biphenylyl, or terphenylyl.
- R 2 is independently methyl or
- Ar is a group of groups represented by the following formulas (Ar1-1), (Ar2-1), (Ar2-8), (Ar2-12), and (Ar2-21)
- Z is independently a divalent group represented by the following formula (4).
- at least one hydrogen of each group may be replaced by alkyl having 1 to 4 carbon atoms or aryl having 6 to 18 carbon atoms.
- Ar is one selected from the group of groups represented by the following formulas (Ar1-1) and (Ar2-1): At least one hydrogen of the formulas (Ar1-1) and (Ar2-1) may be replaced with alkyl having 1 to 4 carbon atoms or aryl having 6 to 18 carbon atoms.
- a pair of electrodes composed of an anode and a cathode, a light emitting layer disposed between the pair of electrodes, an electron transport material according to the item [9], disposed between the cathode and the light emitting layer.
- An organic electroluminescent device having an electron transport layer and / or an electron injection layer containing
- a pair of electrodes composed of an anode and a cathode, a light emitting layer disposed between the pair of electrodes, an electron transport material according to the item [9], disposed between the cathode and the light emitting layer.
- An organic electroluminescent device comprising an electron transport layer and an electron injection layer.
- At least one of the electron transport layer and the electron injection layer further includes an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, or an alkaline earth. Containing at least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes
- the organic electroluminescence device according to any one of [10] to [12].
- the compound of the present invention is stable even when a voltage is applied in a thin film state and has a feature of high charge transport capability.
- the compound of the present invention is suitable as a charge transport material in an organic EL device.
- the compound of the present invention for the electron transport layer of an organic EL device, it is possible to achieve a good balance of improvements in characteristics such as driving voltage reduction, high efficiency, and long life.
- a high-performance display device such as full-color display can be created.
- the first invention of the present application is a compound having cyanopyridyl represented by the following formula (1).
- Ar is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms. At least one hydrogen of these groups may be replaced with an alkyl having 1 to 4 carbon atoms.
- m is an integer of 1 to 4, and when m is 2, 3 or 4, the groups formed by the pyridine ring and L may be the same or different.
- L is a single bond or one selected from the group of divalent groups represented by the following formulas (L-1) and (L-2).
- X 1 to X 6 are independently ⁇ CR 1 — or ⁇ N—, and at least two of X 1 to X 6 are ⁇ CR 1 —, and X 1 to R 1 in two ⁇ CR 1 — of X 6 is a bond bonded to Ar or a pyridine ring, and R 1 in other ⁇ CR 1 — is hydrogen.
- X 7 to X 14 are independently ⁇ CR 1 — or ⁇ N—, and at least two of X 7 to X 14 are ⁇ CR 1 —, and X 7 to R 1 in two ⁇ CR 1 — of X 14 is a bond bonded to Ar or a pyridine ring, and R 1 in other ⁇ CR 1 — is hydrogen.
- At least one hydrogen of L may be replaced by alkyl having 1 to 4 carbons or aryl having 6 to 18 carbons.
- At least one hydrogen of the pyridine ring may be replaced with alkyl having 1 to 4 carbon atoms, phenyl or naphthyl.
- the alkyl having 1 to 4 carbon atoms may be either a straight chain or a branched chain. That is, a straight-chain alkyl having 1 to 4 carbon atoms or a branched alkyl having 3 or 4 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl, and methyl, ethyl, or t-butyl is more preferable.
- one selected from the group of groups represented by formulas (Ar1-1) to (Ar1-7) is more preferable, and formula (Ar1-1) is more preferable.
- Z is independently selected from the group of —O—, —S—, or a divalent group represented by the following formulas (2) and (3). It is preferable that it is one selected from the group of divalent groups represented by formulas (2) and (3). At least one hydrogen of each group may be replaced with alkyl having 1 to 4 carbon atoms or aryl having 6 to 18 carbon atoms.
- R 1 is phenyl, naphthyl, biphenylyl, or terphenylyl.
- R 2 is independently methyl or phenyl, and R 2 is linked to each other to form a ring. May be. Specifically, a structure in which two ortho positions of phenyl are connected by a single bond to form a spiro ring can be exemplified.
- one selected from the group of groups represented by the following formulas (Ar2-1) to (Ar2-21) is preferable.
- one selected from the group of groups represented by formulas (Ar2-1) to (Ar2-12) and (Ar-2-21) is more preferable, and formulas (Ar2-1), (Ar2 More preferably, it is one selected from the group of groups represented by -8), (Ar2-12), and (Ar2-21).
- Z is independently selected from the group of —O—, —S—, or a divalent group represented by the following formulas (2) and (3). It is preferable that it is one selected from the group of divalent groups represented by formulas (2) and (3). At least one hydrogen of each group may be replaced by alkyl having 1 to 4 carbon atoms or aryl having 6 to 12 carbon atoms.
- R 1 is phenyl, naphthyl, biphenylyl, or terphenylyl.
- R 2 is independently methyl or phenyl, and R 2 is linked to each other to form a ring. May be. Specifically, a structure in which two ortho positions of phenyl are connected by a single bond to form a spiro ring can be exemplified.
- Z is more preferably the following formula (4).
- One hydrogen may be replaced by alkyl having 1 to 4 carbon atoms or aryl having 6 to 18 carbon atoms.
- the alkyl having 1 to 4 carbon atoms in which one hydrogen may be replaced may be either a straight chain or a branched chain. That is, a straight-chain alkyl having 1 to 4 carbon atoms or a branched alkyl having 3 or 4 carbon atoms.
- aryl having 6 to 18 carbon atoms in which one hydrogen may be replaced include monocyclic aryl phenyl, (o-, m-, p-) tolyl, (2,3-, 2,4 -, 2,5-, 2,6-, 3,4-, 3,5-) xylyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-) cumenyl, bicyclic (2-, 3-, 4-) biphenylyl which is a series aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, terphenylyl (m-terphenyl-2′-yl) which is a tricyclic aryl, m-terphenyl-4'-yl
- Preferred examples of preferred “aryl having 6 to 18 carbon atoms” are phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl, or m-terphenyl-5′-yl.
- the linking group represented by formula (L-1) is specifically preferably a benzene ring, pyridine ring, pyrimidine ring, pyrazine ring or pyrididazine ring, and is preferably a benzene ring or pyridine ring. More preferably.
- the linking group represented by formula (L-2) is specifically preferably a naphthalene ring, a quinoline ring, an isoquinoline ring or a quinoxaline ring, and more preferably a naphthalene ring.
- specific examples of the group formed by the pyridine ring and L are 4- (6-cyanopyridin-2-yl) phenyl, 4- (5-cyanopyridin-2-yl) phenyl, 4- (4-cyanopyridin-2-yl) phenyl, 4- (3-cyanopyridin-2-yl) phenyl, 4- (2-cyanopyridin-3-yl) phenyl, 4- (6-cyanopyridin-3- Yl) phenyl, 4- (5-cyanopyridin-3-yl) phenyl, 4- (4-cyanopyridin-3-yl) phenyl, 4- (3-cyanopyridin-4-yl) phenyl, 4- (2 -Cyanopyridin-4-yl) phenyl, 3- (6-cyanopyridin-2-yl) phenyl, 3- (5-cyanopyridin-2-yl) phenyl, 3- (4-cyanopyridin-2-yl) Ph
- 6- (6-Cyanopyridin-2-yl) naphthalen-2-yl, 6- (5-cyanopyridin-2-yl) naphthalen-2-yl, 6- (4-cyanopyridin-2-yl) naphthalene- 2-yl, 6- (3-cyanopyridin-2-yl) naphthalen-2-yl, 6- (6-cyanopyridin-3-yl) naphthalen-2-yl, 2- (5-cyanopyridin-3- Yl) naphthalen-6-yl, 6- (4-cyanopyridin-3-yl) naphthalen-2-yl, 6- (2-cyanopyridin-3-yl) naphthalen-2-yl, 6- (3-cyano Pyridin-4-yl) naphthalen-2-yl, 6- (2-cyanopyridin-4-yl) naphthalen-2-yl,
- 6- (6-Cyanopyridin-2-yl) pyrazin-2-yl, 6- (5-cyanopyridin-2-yl) pyrazin-2-yl, 6- (4-cyanopyridin-2-yl) pyrazin- 2-yl, 6- (3-cyanopyridin-2-yl) pyrazin-2-yl, 6- (6-cyanopyridin-3-yl) pyrazin-2-yl, 6- (5-cyanopyridin-3- Yl) pyrazin-2-yl, 6- (4-cyanopyridin-3-yl) pyrazin-2-yl, 6- (2-cyanopyridin-3-yl) pyrazin-2-yl, 6- (3-cyano Pyridin-4-yl) pyrazin-2-yl, 6- (2-cyanopyridin-4-yl) pyrazin-2-yl,
- 6-cyanopyridin-2-yl 5-cyanopyridin-2-yl
- 4-cyanopyridin-2-yl 3-cyanopyridin-2-yl
- 6-cyanopyridin-3-yl 5-cyanopyridin- 3-yl
- 4-cyanopyridin-3-yl 2-cyanopyridin-3-yl
- 2-cyanopyridin-3-yl 3-cyanopyridin-4-yl
- 2-cyanopyridin-4-yl 2-cyanopyridin-4-yl
- preferred groups are 4- (6-cyanopyridin-2-yl) phenyl, 4- (5-cyanopyridin-2-yl) phenyl, 4- (4-cyanopyridin-2-yl) phenyl, 4- (3-cyanopyridin-2-yl) phenyl, 4- (2-cyanopyridin-3-yl) phenyl, 4- (6-cyanopyridin-3-yl) phenyl, 4- (5-cyanopyridin- 3-yl) phenyl, 4- (4-cyanopyridin-3-yl) phenyl, 4- (3-cyanopyridin-4-yl) phenyl, 4- (2-cyanopyridin-4-yl) phenyl, 3- (6-cyanopyridin-2-yl) phenyl, 3- (5-cyanopyridin-2-yl) phenyl, 3- (4-cyanopyridin-2-yl) phenyl, 3- (4-cyanopyridin-2-yl) phenyl
- Preferred among the above examples are compounds (1-1-1) to (1-1-80), (1-1-123) to (1-1-185), (1-1-228) to ( 1-1-290), (1-1-333) to (1-1-404), (1-1-447) to (1-1-500), (1-1-525) to (1- 1-548), (1-1-609) to (1-1-620), (1-2-1) to (1-256), (1-2-73) to (1-2- 90), (1-2-109) to (1-2-144), (1-2-169) to (1-2-204), (1-2-229) to (1-2-264) , (1-2-289) to (1-2312), (1-2-361) to (1-2-373), (1-2506) to (1-2-515), and (1-3-1) to (1-3-50).
- the compound of the present invention is basically obtained by using a known compound and a known synthesis method such as Suzuki coupling reaction or Negishi coupling reaction (for example, “Metal-Catalyzed Cross-Coupling Reactions-Second, Completely Revised and Enlarged”). Can be synthesized using the “Edition”. It can also be synthesized by combining both reactions.
- Suzuki coupling reaction or Negishi coupling reaction for example, “Metal-Catalyzed Cross-Coupling Reactions-Second, Completely Revised and Enlarged”.
- Negishi coupling reaction for example, “Metal-Catalyzed Cross-Coupling Reactions-Second, Completely Revised and Enlarged”. Can be synthesized using the “Edition”. It can also be synthesized by combining both reactions.
- a scheme for synthesizing the compound of the present invention by Suzuki coupling reaction or Negishi coupling reaction is illustrated below.
- cyanobromopyridine is lithiated using an organolithium reagent or converted to a Grignard reagent using an organomagnesium reagent, and trimethyl borate, triethyl borate, triisopropyl borate, etc.
- a diboronic acid ester of cyanopyridine can be synthesized.
- a boronic acid of cyanopyridine can be synthesized by hydrolyzing the boronic acid ester of cyanopyridine.
- R represents a linear or branched alkyl group, preferably a linear or branched alkyl group having 1 to 4 carbon atoms.
- cyanobromopyridine and bis (pinacolato) diboron or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane are used with a palladium catalyst and a base.
- the boronic acid ester can also be synthesized by a coupling reaction.
- Cyanobromopyridine may be a commercially available product.
- boronic acids or boronic acid esters can optionally be subjected to the following coupling reaction.
- boronic acids not only cyanopyridine but also boronic acids and boronic acid esters of a certain substrate may be collectively referred to as “boronic acids”.
- diboronic acid and diboronic acid ester of a certain substrate may be collectively abbreviated as “diboronic acid”.
- cyanobromopyridine is lithiated using an organolithium reagent, or magnesium or an organomagnesium reagent is used as a Grignard reagent, and zinc chloride or a zinc chloride tetramethylethylenediamine complex (ZnCl 2 By reacting with TMEDA), a zinc complex of cyanopyridine can be synthesized.
- a synthesis method using 3-bromo-5-cyanopyridine as a raw material has been illustrated, but a zinc complex can be similarly synthesized even if various cyanobromopyridines are used as a raw material.
- R represents a linear or branched alkyl group, preferably a linear or branched alkyl group having 1 to 4 carbon atoms.
- R can synthesize
- the compound according to the present invention can be synthesized by linking Ar with a compound in which L having a highly reactive atom and cyanopyridine synthesized in this way are linked.
- a synthesis method using the Suzuki coupling reaction will be described.
- the diboronic acid of Ar can be synthesized from the dibromo form of Ar according to the method shown in the above formulas (1) to (3). it can.
- the definition of R in the following formula is the same as the above reaction formula (5).
- reaction formula (12) by reacting a dibromo compound of Ar with a boronic acid compound of a compound in which 2-fold moles of cyanopyridine and L are linked in the presence of a palladium catalyst and a base, the present invention. It is also possible to synthesize a compound according to.
- the boronic acids of the compound in which cyanopyridine and L are linked are synthesized from the compound in which L having an atom highly reactive with cyanopyridine is linked by a method according to the above reaction formulas (1) to (3). can do.
- the compound according to the present invention can be synthesized by using the Negishi coupling reaction instead of the Suzuki coupling reaction. This will be described below.
- R represents a linear or branched alkyl group, preferably a linear or branched alkyl group having 1 to 4 carbon atoms.
- R can synthesize
- the compound was synthesized by a method according to the above reaction formula (5) from a compound in which L having a highly reactive atom with cyanopyridine was linked to a dibromo form of Ar.
- the compound according to the present invention can also be synthesized by reacting mol of cyanopyridine with a zinc complex of L in the presence of a palladium catalyst.
- the compound according to the present invention can also be synthesized by using a method in which L is bonded to a desired position of Ar and a cyanopyridyl group is bonded to L.
- L is bonded to a desired position of Ar
- a cyanopyridyl group is bonded to L.
- R ′ represents a linear or branched alkyl group, preferably a linear or branched alkyl group having 1 to 4 carbon atoms.
- diboronic acids that can be synthesized from a compound in which L having an atom highly reactive with anthracene is bonded by a method according to the above reaction formulas (1) to (3).
- the compound according to the present invention can be synthesized by reacting 2 moles of cyano-substituted bromopyridine with a palladium catalyst in the presence of a base.
- Boronic acids can be synthesized by a method according to the above reaction formulas (1) to (3).
- a dizinc complex that can be synthesized by a method according to the above reaction formula (5) from a compound in which L having an atom having high reactivity with an anthracene ring is linked.
- a compound according to the present invention can be synthesized by reacting 2-fold mole of cyanobromopyridine in the presence of a palladium catalyst.
- 9-phenylanthracene is synthesized as shown in the following reaction formula (22). Bromobenzene is reacted with metallic magnesium in THF to give a Grignard reagent, which is reacted with 9-bromoanthracene in the presence of a catalyst to give 9-phenylanthracene.
- the coupling of the benzene ring and the anthracene ring is not limited to the above-described method, and it can be performed by the Negishi coupling reaction, the Suzuki coupling reaction, or the like, and these conventional methods can be appropriately used depending on the situation. Further, 9-phenylanthracene may be a commercially available product.
- N-bromosuccinimide N-bromosuccinimide
- bromine a commonly used brominating agent other than N-bromosuccinimide such as bromine can be used.
- an anthracene ring and a naphthalene ring are coupled.
- 2-bromo-6-methoxynaphthalene is used as a Grignard reagent according to a conventional method, and this is reacted with 9-bromo-10-phenylanthracene in the presence of a catalyst to give 9- (6-methoxynaphthalen-2-yl) -10. Synthesize phenylanthracene.
- the methoxy group of 9- (6-methoxynaphthalen-2-yl) -10-phenylanthracene is demethylated to naphthol using boron tribromide.
- reagents commonly used in demethylation reactions such as pyridine hydrochloride, can be used as appropriate.
- OH of naphthol is converted to trifluoromethylsulfonate (triflate) using trifluoromethanesulfonic anhydride in the presence of a base such as pyridine.
- -OTf in the reaction formula is an abbreviation for -OSO 2 CF 3 .
- the compound according to the present invention can be synthesized by the Suzuki coupling reaction of the boronic acid ester obtained in the above reaction formula (27) and the cyano-substituted bromopyridine.
- the compound according to the present invention can be synthesized by reacting the triflate with a boronic acid of a cyano-substituted pyridine obtained by the above reaction formulas (1) to (3) as shown in the following reaction formula (29). Can do.
- the compound according to the present invention can also be synthesized by Negishi coupling reaction of triflate with a zinc complex of cyano-substituted pyridine obtained by the above reaction formula (5) as shown in the following reaction formula (30).
- the present invention can be synthesized by synthesizing according to the methods described in the above formulas (8) to (14) using other monobromo compounds of Ar.
- the compound which concerns on can be synthesize
- the bromo isomer of Ar is reacted with the boronic acid of cyanopyridine obtained in the above reaction formulas (1) to (3) in the presence of a palladium catalyst and a base, or
- the compound according to the present invention can be synthesized by reacting the cyanopyridine zinc complex obtained in (5) in the presence of a palladium catalyst.
- the compound according to the present invention can be similarly synthesized by reacting an Ar boronic acid with cyanobromopyridine in the presence of a palladium catalyst and a base, or reacting an Ar zinc complex and cyanobromopyridine with a palladium catalyst. be able to.
- a highly reactive atom or Ar having a functional group (hereinafter collectively referred to as “reactive site”) is reacted with cyanopyridine having one equivalent reactive site or a compound in which L having a reactive site is linked to cyanopyridine.
- this intermediate is reacted with cyanopyridine having a reactive site different from the above or a compound in which L having a reactive site is bonded to cyanopyridine. That is, the reaction may be performed in two or more stages.
- a method of synthesizing by the following procedure can be mentioned.
- the amount of brominating agent used in this case is about 1 ⁇ 2 of that for obtaining a dibromo compound.
- Boronic acid which is a compound in which equimolar cyanopyridine and brominated L are bound to each other, is reacted with the monobromo compound of Ar in the presence of a palladium catalyst and a base to synthesize a mono-substituted product. This mono-substituted product is further brominated.
- the obtained compound is reacted in the same manner with a boronic acid of a compound in which cyanopyridine different from the first reaction and brominated L are bonded to each other to give two different “groups formed from cyanopyridine and L”.
- a compound represented by the formula (1) can be synthesized.
- a zinc complex can be reacted in the presence of a palladium catalyst instead of boronic acids.
- the compound in which the coupling group L is a single bond is also compoundable by substituting the compound which the cyanopyridine and brominated L couple
- the compound represented by the formula (1) includes a compound in which at least one hydrogen is replaced with deuterium.
- a derivative uses a deuterated raw material at a desired position. Thus, it can be synthesized in the same manner as described above.
- the palladium catalyst used in the Suzuki coupling reaction include tetrakis (triphenylphosphine) palladium (0): Pd (PPh 3 ) 4 , bis (triphenylphosphine) palladium (II) dichloride: PdCl 2 (PPh 3 ) 2 , palladium (II) acetate: Pd (OAc) 2 , tris (dibenzylideneacetone) dipalladium (0): Pd 2 (dba) 3 , tris (dibenzylideneacetone) dipalladium (0) chloroform complex: Pd 2 (Dba) 3 ⁇ CHCl 3 , or bis (dibenzylideneacetone) palladium (0): Pd (dba) 2 .
- a phosphine compound may be added to these palladium compounds in some cases.
- the phosphine compound include tri (t-butyl) phosphine, tricyclohexylphosphine, 1- (N, N-dimethylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (N, N-dibutylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (methoxymethyl) -2- (di-t-butylphosphino) ferrocene, 1,1′-bis (di-t-butylphos Fino) ferrocene, 2,2′-bis (di-t-butylphosphino) -1,1′-binaphthyl, 2-methoxy-2 ′-(di-t-butylphosphino) -1,1′-binaphthy
- the base used in the reaction include sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, phosphoric acid
- Examples include tripotassium or potassium fluoride.
- solvent used in the reaction examples include benzene, toluene, xylene, 1,2,4-trimethylbenzene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butyl methyl ether, 1,4- Examples include dioxane, methanol, ethanol, cyclopentyl methyl ether, and isopropyl alcohol. These solvents can be appropriately selected and may be used alone or as a mixed solvent. In addition, water can be used in combination with at least one of the above solvents.
- the palladium catalyst used in the Negishi coupling reaction include tetrakis (triphenylphosphine) palladium (0): Pd (PPh 3 ) 4 , bis (triphenylphosphine) palladium (II) dichloride: PdCl 2 (PPh 3 ) 2 , palladium (II) acetate: Pd (OAc) 2 , tris (dibenzylideneacetone) dipalladium (0): Pd 2 (dba) 3 , tris (dibenzylideneacetone) dipalladium (0) chloroform complex: Pd 2 (Dba) 3 ⁇ CHCl 3 , bis (dibenzylideneacetone) palladium (0): Pd (dba) 2 , bis (tri-t-butylphosphino) palladium (0), or (1,1′-bis (diphenylphosphine) Fino) ferrocene) dichlor
- solvent used in the reaction examples include benzene, toluene, xylene, 1,2,4-trimethylbenzene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butyl methyl ether, cyclopentyl methyl ether or 1,4-dioxane.
- solvents can be appropriately selected and may be used alone or as a mixed solvent.
- the compound of the present invention When the compound of the present invention is used for an electron injection layer or an electron transport layer in an organic EL device, it is stable when an electric field is applied. These represent that the compound of the present invention is excellent as an electron injecting material or an electron transporting material for an electroluminescent device.
- the electron injection layer mentioned here is a layer for receiving electrons from the cathode to the organic layer
- the electron transport layer is a layer for transporting the injected electrons to the light emitting layer.
- the electron transport layer can also serve as the electron injection layer.
- the material used for each layer is referred to as an electron injection material and an electron transport material.
- 2nd invention of this application is an organic EL element containing the compound represented by Formula (1) of this invention in an electron injection layer or an electron carrying layer.
- the organic EL element of the present invention has a low driving voltage and high durability during driving.
- the structure of the organic EL device of the present invention has various modes, but is basically a multilayer structure in which at least a hole transport layer, a light emitting layer, and an electron transport layer are sandwiched between an anode and a cathode.
- Examples of the specific configuration of the device are (1) anode / hole transport layer / light emitting layer / electron transport layer / cathode, (2) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer. / Cathode, (3) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode, etc.
- the compound of the present invention Since the compound of the present invention has high electron injection and electron transport properties, it can be used in an electron injection layer or an electron transport layer alone or in combination with other materials.
- the organic EL device of the present invention emits blue, green, red and white light by combining a hole injection layer, a hole transport layer, a light emitting layer, etc. using other materials with the electron transport material of the present invention. It can also be obtained.
- the light-emitting material or light-emitting dopant that can be used in the organic EL device of the present invention is daylight fluorescence as described in the Polymer Society of Japan, Polymer Functional Materials Series “Optical Functional Materials”, Joint Publication (1991), P236. Materials, fluorescent brighteners, laser dyes, organic scintillators, various fluorescent analysis reagents and other luminescent materials, supervised by Koji Koji, “Organic EL materials and displays” published by CMMC (2001) P155-156 And a light emitting material of a triplet material as described in P170 to 172.
- the compounds that can be used as the light emitting material or the light emitting dopant are polycyclic aromatic compounds, heteroaromatic compounds, organometallic complexes, dyes, polymer light emitting materials, styryl derivatives, aromatic amine derivatives, coumarin derivatives, borane derivatives, oxazines. Derivatives, compounds having a spiro ring, oxadiazole derivatives, fluorene derivatives and the like.
- Examples of the polycyclic aromatic compound are anthracene derivatives, phenanthrene derivatives, naphthacene derivatives, pyrene derivatives, chrysene derivatives, perylene derivatives, coronene derivatives, rubrene derivatives, and the like.
- heteroaromatic compounds are oxadiazole derivatives having a dialkylamino group or diarylamino group, pyrazoloquinoline derivatives, pyridine derivatives, pyran derivatives, phenanthroline derivatives, silole derivatives, thiophene derivatives having a triphenylamino group, quinacridone derivatives Etc.
- organometallic complexes examples include zinc, aluminum, beryllium, europium, terbium, dysprosium, iridium, platinum, osmium, gold, etc., quinolinol derivatives, benzoxazole derivatives, benzothiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, A complex with a benzimidazole derivative, a pyrrole derivative, a pyridine derivative, a phenanthroline derivative, or the like.
- dyes are xanthene derivatives, polymethine derivatives, porphyrin derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, oxobenzanthracene derivatives, carbostyril derivatives, perylene derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazoles And pigments such as derivatives.
- the polymer light-emitting material include polyparaphenyl vinylene derivatives, polythiophene derivatives, polyvinyl carbazole derivatives, polysilane derivatives, polyfluorene derivatives, polyparaphenylene derivatives, and the like.
- styryl derivatives are amine-containing styryl derivatives, styrylarylene derivatives, and the like.
- electron transport materials used in the organic EL device of the present invention are arbitrarily selected from compounds that can be used as electron transport compounds in photoconductive materials and compounds that can be used in the electron transport layer and electron injection layer of organic EL devices. Can be used.
- electron transport materials include quinolinol metal complexes, 2,2′-bipyridyl derivatives, phenanthroline derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, oxine derivatives.
- a compound conventionally used as a charge transport material for holes or a hole injection of an organic EL device is used in a photoconductive material.
- Any known material used for the layer and the hole transport layer can be selected and used. Specific examples thereof include carbazole derivatives, triarylamine derivatives, phthalocyanine derivatives, and the like.
- Each layer constituting the organic EL element of the present invention can be formed by forming a material to constitute each layer into a thin film by a method such as a vapor deposition method, a spin coating method, or a casting method.
- the film thickness of each layer thus formed is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm.
- a vapor deposition method as a method of thinning the light emitting material from the standpoint that a homogeneous film can be easily obtained and pinholes are hardly generated.
- the vapor deposition conditions differ depending on the type of the light emitting material of the present invention.
- Deposition conditions generally include boat heating temperature 50 to 400 ° C., vacuum degree 10 ⁇ 6 to 10 ⁇ 3 Pa, deposition rate 0.01 to 50 nm / second, substrate temperature ⁇ 150 to + 300 ° C., film thickness 5 nm to 5 ⁇ m. It is preferable to set appropriately within the range.
- the organic EL device of the present invention is preferably supported by a substrate in any of the structures described above.
- the substrate only needs to have mechanical strength, thermal stability, and transparency, and glass, a transparent plastic film, and the like can be used.
- the anode material metals, alloys, electrically conductive compounds and mixtures thereof having a work function larger than 4 eV can be used. Specific examples thereof include metals such as Au, CuI, indium tin oxide (hereinafter abbreviated as ITO), SnO 2 , ZnO, and the like.
- the cathode material metals, alloys, electrically conductive compounds, and mixtures thereof having a work function smaller than 4 eV can be used. Specific examples thereof are aluminum, calcium, magnesium, lithium, magnesium alloy, aluminum alloy and the like. Specific examples of the alloy include aluminum / lithium fluoride, aluminum / lithium, magnesium / silver, and magnesium / indium. In order to efficiently extract light emitted from the organic EL element, it is desirable that at least one of the electrodes has a light transmittance of 10% or more.
- the sheet resistance as the electrode is preferably several hundred ⁇ / ⁇ or less.
- the film thickness depends on the properties of the electrode material, it is usually set in the range of 10 nm to 1 ⁇ m, preferably 10 to 400 nm.
- Such an electrode can be produced by forming a thin film by a method such as vapor deposition or sputtering using the electrode material described above.
- an organic material comprising the above-mentioned anode / hole injection layer / hole transport layer / light emitting layer / electron transport material of the present invention / cathode is used.
- a method for creating an EL element will be described.
- a thin film of an anode material is formed on a suitable substrate by vapor deposition to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode.
- a light emitting layer thin film is formed thereon.
- the electron transport material of this invention is vacuum-deposited, a thin film is formed, and it is set as an electron carrying layer.
- the target organic EL element is obtained by forming the thin film which consists of a substance for cathodes by a vapor deposition method, and making it a cathode.
- the production order can be reversed, and the cathode, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be produced in this order.
- the anode When a DC voltage is applied to the organic EL device thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, a transparent or translucent electrode is applied. Luminescence can be observed from the side (anode or cathode, and both). The organic EL element also emits light when an alternating voltage is applied.
- the alternating current waveform to be applied may be arbitrary.
- the reaction solution was cooled to room temperature and extracted with toluene, and then the organic layer was dried over sodium sulfate.
- reaction solution was cooled to room temperature, and the precipitated crystals were collected by filtration, washed with water, and purified by a silica gel short column (developing solvent toluene) to obtain 106.0 g of 2-phenylanthraquinone.
- the reaction solution was cooled to room temperature, water was added, extraction was performed with toluene, and then the organic layer was dried over magnesium sulfate.
- the crude product obtained by distilling off the solvent under reduced pressure was purified with a silica gel short column (developing solvent toluene), and 2,2 ′-((2-phenylanthracene-9,10-diyl) bis (4,1- 11.5 g of phenylene)) bis (4,4,5,5-tetramethyl-1.3.2-dioxaborolane) were obtained.
- reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation extraction.
- the organic layer was separated, dried and concentrated, passed through an activated carbon short column (developing solution: toluene), concentrated and reprecipitated with heptane to obtain the target compound (6.70 g).
- reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation extraction.
- reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation extraction.
- the organic layer was separated, dried and concentrated, passed through an activated carbon short column (developing solution: toluene), concentrated and reprecipitated with heptane to obtain the desired compound (9.00 g).
- reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation extraction.
- reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation extraction.
- reaction solution was cooled to room temperature, water was added, and toluene was further added for liquid separation extraction.
- Tables 1 and 2 show the material configurations of the respective layers in the devices according to Examples 1 to 6 and Comparative Examples 1 to 8 that were manufactured.
- HI-1 represents N 4 , N 4 ′ -diphenyl-N 4 , N 4 ′ -bis (9-phenyl-9H-carbazol-3-yl)-[1,1′- Biphenyl] -4,4′-diamine
- IL is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile
- HT-1 is N-([1,1′-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine
- BH is 9-phenyl -10- (4-phenylnaphthalen-1-yl) anthracene
- BD is 7,7-dimethyl-N 5 , N 9 -diphenyl-N 5 , N 9 -bis (4- (trimethylsilyl) phenyl) -7H -
- Example 1 Element Using Compound (1-1-2) as Electron Transport Material ITO coated to a thickness of 180 nm by sputtering was polished to 150 nm, and was a 26 mm ⁇ 28 mm ⁇ 0.7 mm glass substrate (( Opt Science Co., Ltd.) was used as a transparent support substrate.
- This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), a molybdenum vapor deposition boat containing HI-1, a molybdenum vapor deposition boat containing IL, and HT-1.
- the following layers were sequentially formed on the ITO film of the transparent support substrate. Depressurize the vacuum chamber to 5 ⁇ 10 ⁇ 4 Pa, first heat the vapor deposition boat containing HI-1 to a film thickness of 40 nm, and further heat the vapor deposition boat containing IL. A hole injection layer composed of two layers is formed by vapor deposition so as to have a film thickness of 5 nm, and then the vapor deposition boat containing HT-1 is heated to vaporize to a film thickness of 25 nm. A transport layer was formed.
- the vapor deposition boat containing BH and the vapor deposition boat containing BD were heated at the same time to form a light emitting layer by vapor deposition so as to have a film thickness of 20 nm.
- the deposition rate was adjusted so that the weight ratio of BH to BD was approximately 95: 5.
- the vapor deposition boat containing the compound (1-1-2) and the vapor deposition boat containing Liq were heated at the same time so as to have a film thickness of 30 nm to form an electron transport layer.
- the deposition rate was adjusted so that the weight ratio of the compound (1-1-2) and Liq was about 1: 1.
- the deposition rate of each layer was 0.01 to 1 nm / second.
- the evaporation boat containing Liq was heated to deposit at a deposition rate of 0.01 to 0.1 nm / second so as to have a film thickness of 1 nm.
- a boat containing magnesium and a boat containing silver were heated at the same time, and deposited to a film thickness of 100 nm to form a cathode to obtain an organic EL device.
- the deposition rate was adjusted between 0.1 nm and 10 nm / second so that the atomic ratio of magnesium and silver was 10: 1.
- the characteristics at 1000 cd / m 2 emission were measured.
- the driving voltage was 4.25 V and the external quantum efficiency was 4.25%.
- the time during which the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was maintained was 270 hours.
- the driving voltage is 4.21 V
- the external quantum efficiency is 3.75%
- the constant current is obtained at a current density at which a luminance of 1500 cd / m 2 is obtained.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 157 hours.
- Example 3 Device Using Compound (1-2-48) as Electron Transport Material According to the method of Example 1 except that compound (1-1-2) was replaced with compound (1-2-48) Thus, an organic EL element was obtained.
- the driving voltage is 4.47 V
- the external quantum efficiency is 4.21%
- the constant current is obtained at a current density at which a luminance of 1500 cd / m 2 is obtained.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 298 hours.
- Example 4 Device Using Compound (1-2-173) as Electron Transport Material According to the method of Example 1 except that compound (1-1-2) was replaced with compound (1-2-173) Thus, an organic EL element was obtained.
- the driving voltage is 4.30 V
- the external quantum efficiency is 7.20%
- the constant current is obtained at a current density at which a luminance of 1500 cd / m 2 is obtained.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 312 hours.
- Example 5 Device Using Compound (1-2-179) as Electron Transport Material According to the method of Example 1 except that compound (1-1-2) was replaced with compound (1-2-179) Thus, an organic EL element was obtained.
- the driving voltage is 4.20 V
- the external quantum efficiency is 4.96%
- the constant current is obtained at a current density at which a luminance of 1500 cd / m 2 is obtained.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 292 hours.
- Example 6 Device using compound (1-2-506) as electron transporting material The method of Example 1 was followed except that compound (1-1-2) was replaced with compound (1-2-506). Thus, an organic EL element was obtained.
- the driving voltage is 4.23 V
- the external quantum efficiency is 4.75%
- the constant current is obtained at a current density at which a luminance of 1500 cd / m 2 is obtained.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 303 hours.
- Table 3 summarizes the results of Examples 1 to 6 and Comparative Examples 1 to 6.
- Example 7 Device Using Compound (1-248) as Electron Transport Material for Device Having Electron Transport Layer and Electron Injection Layer
- compound (1 The evaporation boat containing -2-48) was heated and evaporated to a thickness of 10 nm to form an electron transport layer.
- the vapor deposition boat containing the compound (1-2-48) and the vapor deposition boat containing Liq were heated at the same time so as to have a film thickness of 20 nm to form an electron injection layer.
- the deposition rate was adjusted so that the weight ratio of Compound I to Liq was approximately 1: 1.
- the deposition rate of each layer was 0.01 to 1 nm / second.
- a Liq layer and a cathode were formed in the same manner as in Example 1 to obtain an organic EL device.
- the characteristics at 1000 cd / m 2 emission were measured.
- the driving voltage was 4.63 V and the external quantum efficiency was 5.05%.
- the time during which the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was maintained was 420 hours.
- Example 8 Device Using Compound (1-2-173) as Electron Transport Material for Device Having Electron Transport Layer and Electron Injection Layer Compound (1-2-48) to Compound (1-2-173)
- An organic EL device was obtained in accordance with the method of Example 7 except for that.
- the driving voltage is 3.49 V
- the external quantum efficiency is 7.59%
- the constant current is obtained at a current density at which a luminance of 1500 cd / m 2 is obtained.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 373 hours.
- Example 9 Device Using Compound (1-2-179) as Electron Transport Material for Device Having Electron Transport Layer and Electron Injection Layer Compound (1-2-48) to Compound (1-2-179)
- An organic EL device was obtained in accordance with the method of Example 7 except for that.
- the driving voltage is 4.18 V
- the external quantum efficiency is 5.88%
- the constant current is obtained at a current density that can obtain a luminance of 1500 cd / m 2.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 395 hours.
- Example 10 Device Using Compound (1-2-506) as Electron Transport Material for Device Having Electron Transport Layer and Electron Injection Layer Compound (1-2-48) to Compound (1-2-506)
- An organic EL device was obtained in accordance with the method of Example 7 except for that.
- the driving voltage is 4.26 V
- the external quantum efficiency is 5.52%
- the constant current is obtained at a current density that can obtain a luminance of 1500 cd / m 2.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 255 hours.
- Comparative Example 7 Device Using Compound G as Electron Transport Material for Device Having Electron Transport Layer and Electron Injection Layer According to the method of Example 7, except that Compound (1-2-48) was replaced with Compound G.
- An organic EL device was obtained.
- the driving voltage is 4.02 V
- the external quantum efficiency is 5.79%
- the constant current is obtained at a current density that can obtain a luminance of 1500 cd / m 2.
- the time during which the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was maintained was 202 hours.
- An organic EL device was obtained.
- the driving voltage is 3.73 V
- the external quantum efficiency is 6.29%
- the constant current is obtained at a current density at which a luminance of 1500 cd / m 2 is obtained.
- the time for maintaining the luminance of 80% (1200 cd / m 2 ) or more of the initial luminance was 172 hours.
- anthracene-9,10-dicarboxaldehyde and 4-tertiary butylacetophenone are condensed under basic conditions to obtain an enone compound in advance.
- the pyridinium salt was reacted after being synthesized separately, but although a small amount of a plurality of products could be confirmed, most of the raw enone compound was recovered without being reacted, and compound J was not obtained. .
- an organic EL element such as a low driving voltage, high efficiency, and a long lifetime
- an organic EL element characterized by a particularly long lifetime A high-performance display device such as a full-color display can be provided.
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Abstract
Description
[1] 下記式(1)で表される化合物;
mは1~4の整数であり、mが2、3または4であるとき、ピリジン環とLで形成される基は同一でもよく、異なっていてもよく;
Lは単結合または下記式(L-1)および(L-2)で表される2価の基の群から選ばれる1つであり、
式(L-2)中、X7~X14は独立して=CR1-または=N-であり、X7~X14の内の少なくとも2つは=CR1-であり、X7~X14の内の2つの=CR1-におけるR1はArまたはピリジン環と結合する結合手であり、それ以外の=CR1-におけるR1は水素であり、
Lの少なくとも1つの水素は炭素数1~4のアルキルまたは炭素数6~18のアリールで置き換えられていてもよく;
ピリジン環の少なくとも1つの水素は炭素数1~4のアルキル、フェニルまたはナフチルで置き換えられていてもよく;そして、
式(1)中の各々の環およびアルキルの少なくとも1つの水素は重水素で置き換えられていてもよい。
式(Ar1-1)(Ar2-1)、(Ar2-8)、(Ar2-12)、および(Ar2-21)中、Zは独立して、下記式(4)で表される2価の基であり、それぞれの基の少なくとも1つの水素は炭素数1~4のアルキルまたは炭素数6~18のアリールで置き換えられていてもよい。
本発明の化合物の具体例は以下に列記する式によって示されるが、本発明はこれらの具体的な構造の開示によって限定されることはない。
次に、本発明の化合物の製造方法について説明する。本発明の化合物は、基本的には公知の化合物を用いて、公知の合成法、例えば鈴木カップリング反応や根岸カップリング反応(例えば、「Metal-Catalyzed Cross-Coupling Reactions - Second, Completely Revised and Enlarged Edition」などに記載)を利用して合成することができる。また、両反応を組み合わせても合成することができる。本発明の化合物を、鈴木カップリング反応または根岸カップリング反応で合成するスキームを以下に例示する。
<シアノピリジンのボロン酸またはボロン酸エステル類の合成>
下記反応式(1)に示すように、シアノブロモピリジンを、有機リチウム試薬を用いてリチオ化するか、有機マグネシウム試薬を用いてグリニャール試薬とし、ホウ酸トリメチル、ホウ酸トリエチルまたはホウ酸トリイソプロピルなどと反応させることにより、シアノピリジンのジボロン酸エステルを合成することができる。さらに、下記反応式(2)に示すように、このシアノピリジンのボロン酸エステルを加水分解することにより、シアノピリジンのボロン酸を合成することができる。
次に下記反応式(4)でシアノピリジンのボロン酸類と、Lとなる1,3-ジブロモベンゼン、1,4-ジブロモベンゼン、2,6-ジブロモピリジン、3,5-ジブロモピリジン、2,5-ジブロモピリジンなどの所望の化合物を反応させることにより、Arに連結させる前駆体であるシアノピリジンと反応性の高い原子を持つLが連結した化合物を合成することができる。ここでは、前記のジブロモ体の代わりにブロモヨード体やジヨード体を用いることもできる。また、ここでは原料として3-ブロモ-5-シアノピリジンを用いた合成法を例示したが、原料として様々なシアノブロモピリジンを用いてシアノピリジンと反応性の高い原子を持つLが連結した化合物を合成することができる。さらに、シアノブロモピリジンの代わりにシアノヨードピリジンまたはシアノクロロピリジンを用いてもよい。なお、ここで用いたボロン酸類は上記反応式(1)~(3)のように合成することが可能であるが、市販品を利用してもよい。下記式中のAr’はLに相当する2価の基である。
下記反応式(5)に示すように、シアノブロモピリジンを有機リチウム試薬を用いてリチオ化するか、マグネシウムや有機マグネシウム試薬を用いてグリニャール試薬とし、塩化亜鉛や塩化亜鉛テトラメチルエチレンジアミン錯体(ZnCl2・TMEDA)と反応させることにより、シアノピリジンの亜鉛錯体を合成することができる。ここでは原料として3-ブロモ-5-シアノピリジンを用いた合成法を例示したが、原料として様々なシアノブロモピリジンを用いても、同様に亜鉛錯体を合成することができる。
下記反応式(6)に示すように、シアノピリジンの亜鉛錯体と、Lとなる1,3-ジブロモベンゼン、1,4-ジブロモベンゼン、2,6-ジブロモピリジン、3,5-ジブロモピリジン、2,5-ジブロモピリジンなどの所望の化合物を反応させることにより、Arに連結させる前駆体であるシアノピリジンと反応性の高い原子を持つLが連結した化合物を合成することができる。また、鈴木カップリング法の場合と同様に、前記のジブロモ体の代わりにブロモヨード体やジヨード体を用いることもできる。さらに、原料として3-ブロモ-5-シアノピリジンの代わりに様々なシアノブロモピリジンの亜鉛錯体を用いてシアノピリジンと反応性の高い原子を持つLが連結した化合物を合成することができる。
まず、下記反応式(7)に示すように、Arを適当な臭素化剤を用いて臭素化することにより、Arのジブロモ体が得られる。適当な臭素化剤としては臭素またはN-臭化コハク酸イミド(NBS)が挙げられる。
次に、下記反応式(8)~(10)に示すように、上記式(1)~(3)で示された方法に準じて、Arのジブロモ体からArのジボロン酸類を合成することができる。下記式中のRの定義は前記反応式(5)と同じである。
最後に、下記反応式(11)に示すように、上記のように合成したArのジボロン酸類に、2倍モルのシアノピリジンと反応性の高い原子を持つLが連結した化合物を、パラジウム触媒と塩基の存在下で反応させることにより、本発明に係る化合物を合成することができる。
そして、下記反応式(14)に示すように、上記のように合成した、Arのジ亜鉛錯体に、2倍モルのシアノピリジンと反応性の高い原子を持つLが連結した化合物を、パラジウム触媒の存在下で反応させることにより、本発明に係る化合物を合成することができる。
まず、下記反応式(16)に示すように、Lとなる1,4-ジブロモベンゼン、1,3-ジブロモベンゼン、3,5-ジブロモピリジン、2,6-ジブロモベンゼンなどの所望の化合物に1当量の有機リチウム試薬を用いてリチオ化するか、1当量のマグネシウムや有機マグネシウム試薬を用いてGrignard試薬としてモノメタル化したLのハロ体を合成する。ここではジブロモ体を用いた例を示したが、ジクロロ体またはジヨード体などを用いることもできる。
下記反応式(17)に示すように2倍モルのモノメタル化したLのハロ体とアントラキノンを反応させることでジオール体とし、続いてジオール体を酢酸中でホスフィン酸ナトリウム・1水和物とヨウ化カリウムを反応させることで、アントラセンと反応性の高い原子を持つLが結合した化合物を合成することができる。また、使用するアントラキノンは2-フェニルアントラキノンのような置換基を有するものもよい。
また、下記反応式(18)に示すように、上記のように合成したアントラセンと反応性の高い原子を持つLが結合した化合物に、2倍モルのシアノ置換ピリジンのボロン類を、パラジウム触媒と塩基の存在下で反応させることにより、本発明に係る化合物を合成することができる。このシアノ置換ピリジンのボロン酸類は、上記反応式(1)~(3)に準じた方法で合成することができる。
下記反応式(20)に示すように、上記のように合成したアントラセンと反応性の高い原子を持つLが結合した化合物に、2倍モルのシアノピリジンの亜鉛錯体をパラジウム触媒の存在下で反応させることにより、本発明に係る化合物を合成することができる。
本願の第2の発明は、電子注入層、または電子輸送層に、本発明の式(1)で表される化合物を含有する有機EL素子である。本発明の有機EL素子は、駆動電圧が低く、駆動時の耐久性が高い。
WO2012/060374に記載された方法を参照して合成した、4,4,5,5-テトラメチル-2-(6-(10-フェニルアントラセン-9-イル)ナフタレン-2-イル)-1,3,2-ジオキサボロラン2.53g、3-ブロモ-5-シアノピリジン1.01g、テトラキス(トリフェニルホスフィン)パラジウム(0)0.17g、リン酸三カリウム2.12g、シュードクメン20mL、t-ブチルアルコール5mL、および水1mLをフラスコに入れ、窒素雰囲気下、還流温度で8時間攪拌した。反応液を室温まで冷却し、トルエンで抽出した後、有機層を硫酸ナトリウムで乾燥させた。溶媒を減圧留去して得た粗生成物をシリカゲルカラムクロマトグラフィー(展開溶媒:トルエン/酢酸エチル=95/5(容量比))で精製して、5-シアノ-3-(6-(10-フェニルアントラセン-9-イル)ナフタレン-2-イル)ピリジン0.19gを得た。
1H-NMR(CDCl3): 9.2(d,1H)、 8.9(d,1H)、 8.3(t,1H)、 8.2(d,1H)、 8.2(d,1H)、 8.1(d,1H)、 8.1(s,1H)、 7.8(dd,1H)、 7.8~7.7(m,5H)、 7.6(m,2H)、 7.6(m,1H)、 7.5(m,2H)、 7.4~7.3(m,4H).
<2-フェニルアントラキノンの合成>
2-クロロアントラキノン125.0g、フェニルボロン酸75.4g、テトラキス(トリフェニルホスフィン)パラジウム(0)1.79g、リン酸三カリウム109.3g、シュードクメン400mL、t-ブチルアルコール100mL、および水20mLをフラスコに入れ、窒素雰囲気下、還流温度で3.5時間攪拌した。反応液を室温まで冷却し、析出した結晶をろ取し、水洗した後、シリカゲルショートカラム(展開溶媒トルエン)で精製して、2-フェニルアントラキノン106.0gを得た。
1,4-ジブロモベンゼン47.2gと脱水シクロペンチルメチルエーテル250mLをフラスコに入れ-78℃に冷却した。そこへn-ブチルリチウム(2.69Mヘキサン溶液)78mLを撹拌しながら滴加し、滴下後さらに0.5時間撹拌した。そこへ2-フェニルアントラキノン22.7gを加え、そのままの温度で5時間撹拌した。水を加えて反応を停止させ、トルエンで抽出した後、有機層を硫酸マグネシウムで乾燥させた。溶媒を減圧流去して得られた固体をシリカゲルショートカラム(展開溶媒:トルエン/酢酸エチル=4/1(容量比))で精製して、9,10-ビス(4-ブロモフェニル)-2-フェニル-9,10-ジヒドロアントラセン-9,10-ジオール42.5gを得た。
9,10-ビス(4-ブロモフェニル)-2-フェニル-9,10-ジヒドロアントラセン-9,10-ジオール41.9g、ホスフィン酸ナトリウム・1水和物90.3g、ヨウ化カリウム30.2g、酢酸200mLをフラスコに入れ、還流温度で3時間撹拌した。反応液を室温まで冷却し、水を加えて析出した固体をろ取し、水、メタノール、次いで酢酸エチルで洗浄した。この粗生成物をシリカゲルショートカラム(展開溶媒トルエン)で精製して、9,10-(4-ブロモフェニル)-2-フェニルアントラセン38.5gを得た。
9,10-(4-ブロモフェニル)-2-フェニルアントラセン12.0g、ビス(ピナコラート)ジボロン12.2g、(1,1’-ビス(ジフェニルホスフィノ)フェロセン)パラジウム(II)ジクロリド・ジクロロメタン錯体0.49g、酢酸カリウム7.85g、およびシクロペンチルメチルエーテル40mLをフラスコに入れ、還流温度で6時間撹拌した。反応液を室温まで冷却し、水を加え、トルエンで抽出した後、有機層を硫酸マグネシウムで乾燥させた。溶媒を減圧留去して得られた粗生成物をシリカゲルショートカラム(展開溶媒トルエン)で精製し、2、2’-((2-フェニルアントラセン-9,10-ジイル)ビス(4,1-フェニレン))ビス(4,4,5,5-テトラメチル-1.3.2-ジオキサボロラン)11.5gを得た。
2,2’-((2-フェニルアントラセン-9,10-ジイル)ビス(4,1-フェニレン))ビス(4,4,5,5-テトラメチル-1.3.2-ジオキサボロラン)2.69g、3-ブロモ-5-シアノピリジン1.98g、テトラキス(トリフェニルホスフィン)パラジウム(0)0.16g、リン酸三カリウム2.29g、シュードクメン20mL、t-ブチルアルコール5mL、および水1mLをフラスコに入れ、窒素雰囲気下、還流温度で8時間攪拌した。反応液を冷却し、トルエンで抽出した後、有機層を硫酸ナトリウムで乾燥させた。溶媒を減圧留去して得られた粗生成物をシリカゲルカラムクロマトグラフィー(展開溶媒トルエン/酢酸エチル=9/1(容量比))で精製して、9,10-ビス(4-(5-シアノピリジン-3-イル)フェニル)-2-フェニルアントラセン0.1gを得た。
1H-NMR(CDCl3): 9.2(d,2H)、 8.9(dd,2H)、 8.3(m,2H)、 7.9~7.8(m,6H)、 7.8~7.7(m,7H)、 7.6(m,2H)、 7.4(m,4H)、 7.4~7.3(m,1H).
<3-シアノ-5-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)ピリジンの合成>
3-ブロモ-5-シアノピリジン(10g)、ビス(ピナコラート)ジボロン(15.3g)、酢酸カリウム(10.7g)、(1,1’-ビス(ジフェニルホスフィノ)フェロセン)パラジウム(II)ジクロリド・ジクロロメタン錯体(1.34g)、およびシクロペンチルメチルエーテル(100mL)をフラスコに入れ、窒素雰囲気下、還流温度で8時間撹拌した。反応液を室温まで冷却し水を加え、さらにトルエンを加えて分液抽出を行った。有機層を分離後、乾燥、濃縮し、活性炭ショートカラム(展開液:トルエン)を通したのち、濃縮してヘプタンで再沈することで目的物化合物(6.70g)を得た。
特開2014-82479公報に記載の方法で合成した、9,10-ビス(6-ブロモピリジン-2-イル)-2-フェニルアントラセン(3.00g)、3-シアノ-5-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)ピリジン(2.92g)、炭酸カリウム(2.93g)、臭化テトラ-n-ブチルアンモニウム(0.34g)、ビス(ジターシャリーブチル(4-ジメチルアミノフェニル)ホスフィン)ジクロロパラジウム(0.11g)、1,2,4-トリメチルベンゼン(20mL)、および水(2mL)をフラスコに入れ、窒素雰囲気下、還流温度で4時間撹拌した。反応液を室温まで冷却し水を加え、さらにトルエンを加えて分液抽出を行った。有機層を分離後、乾燥、濃縮し、粗体をNHシリカゲルカラム(展開液:トルエン/酢酸エチル=4/1(容量比))で精製したのち、昇華精製して目的物化合物(1.30g)を得た。
1H-NMR(CDCl3): 9.5(d,2H)、 8.9(m,2H)、 8.7(m,2H)、 8.1(dt,2H)、 8.0(dd,2H)、 7.8~7.3(m,14H).
<3-(5-シアノピリジン-3-イル)フェニルブロミドの合成>
3-シアノ-5-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)ピリジン(17.5g)、1-ブロモ-3-ヨードベンゼン(28.0g)、炭酸カリウム(21.0g)、臭化テトラ-n-ブチルアンモニウム(4.90g)、ビス(ジターシャリーブチル(4-ジメチルアミノフェニル)ホスフィン)ジクロロパラジウム(1.61g)、1,2,4-トリメチルベンゼン(100mL)および水(10mL)をフラスコに入れ、窒素雰囲気下、還流温度で8時間撹拌した。反応液を室温まで冷却し水を加え、さらにトルエンを加えて分液抽出を行った。有機層を分離後、乾燥、濃縮し、粗体をNHシリカゲルカラム(展開液:トルエン/酢酸エチル=9/1(容量比))で精製して目的物化合物(6.00g)を得た。
2,7-ジブロモ-5,5’-(9,9’-スピロビ[フルオレン])(8.0g)、ビス(ピナコラート)ジボロン(10.3g)、酢酸カリウム(6.62g)、(1,1’-ビス(ジフェニルホスフィノ)フェロセン)パラジウム(II)ジクロリド・ジクロロメタン錯体(0.41g)、およびシクロペンチルメチルエーテル(100mL)をフラスコに入れ、窒素雰囲気下、還流温度で5時間撹拌した。反応液を室温まで冷却し水を加え、さらにトルエンを加えて分液抽出を行った。有機層を分離後、乾燥、濃縮し、活性炭ショートカラム(展開液:トルエン)を通したのち、濃縮してヘプタンで再沈することで目的物化合物(9.00g)を得た。
2,7-ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)-5,5’-(9,9’-スピロビ[フルオレン])(3.00g)、3-ブロモ-5-シアノピリジン(3.28g)、炭酸カリウム(2.92g)、臭化テトラ-n-ブチルアンモニウム(0.34g)、ビス(ジターシャリーブチル(4-ジメチルアミノフェニル)ホスフィン)ジクロロパラジウム(0.037g)、1,2,4-トリメチルベンゼン(20mL)および水(2mL)をフラスコに入れ、窒素雰囲気下、還流温度で4時間撹拌した。反応液を室温まで冷却し水を加え、さらにトルエンを加えて分液抽出を行った。有機層を分離後、乾燥、濃縮し、粗体をNHシリカゲルカラム(展開液:トルエン/酢酸エチル=4/1(容量比))で精製したのち、昇華精製して目的物化合物(1.78g)を得た。
1H-NMR(CDCl3): 9.0(d,2H)、 8.8(d,2H)、 8.1(t,2H)、 8.0(d,2H)、 7.9(d,2H)、 7.7(dd,2H)、 7.6(t,2H)、 7.5(m,2H)、 7.5~7.4(m,6H)、 7.1(dt,2H)、 7.0(d,2H)、 6.8(d,2H).
2,7-ジブロモ-5,5’-(9,9’-スピロビ[フルオレン])(2.73g)、3-シアノ-5-(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)ピリジン(3.18g)、炭酸カリウム(1.59g)、臭化テトラ-n-ブチルアンモニウム(0.37g)、ビス(ジターシャリーブチル(4-ジメチルアミノフェニル)ホスフィン)ジクロロパラジウム(0.091g)、1,2,4-トリメチルベンゼン(20mL)および水(2mL)をフラスコに入れ、窒素雰囲気下、還流温度で9時間撹拌した。反応液を室温まで冷却し水を加え、さらにトルエンを加えて分液抽出を行った。有機層を分離後、乾燥、濃縮し、粗体をNHシリカゲルカラム(展開液:トルエン/酢酸エチル=4/1(容量比))で精製したのち、昇華精製して目的物化合物(1.59g)を得た。
1H-NMR(CDCl3): 8.9(d,2H)、 8.8(d,2H)、 8.1(d,2H)、 8.0(t,2H)、 7.9(d,2H)、 7.6(dd,2H)、7.4(dt,2H)、 7.2(dt,2H)、 6.9(d,2H)、 6.8(d,2H).
国際公開WO2007/029696公報に記載の方法で合成した4,7-ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)トリフェニレン(1.60g)、3-ブロモ-5-シアノピリジン(1.90g)、炭酸カリウム(1.84g)、臭化テトラ-n-ブチルアンモニウム(0.21g)、ビス(ジターシャリーブチル(4-ジメチルアミノフェニル)ホスフィン)ジクロロパラジウム(0.024g)、1,2,4-トリメチルベンゼン(20mL)および水(2mL)をフラスコに入れ、窒素雰囲気下、還流温度で6時間撹拌した。反応液を室温まで冷却し水を加え、析出物をろ過した。加熱クロロホルムに溶解させたのちにセライト濾過し、さらにピリジンで再結晶を行い精製したのち、昇華精製して目的物化合物(0.98g)を得た。
EI-MS: m/z=584.
2,7-ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)トリフェニレン(2.39g)、3-ブロモ-4-シアノピリジン(2.00g)、炭酸カリウム(2.75g)、臭化テトラ-n-ブチルアンモニウム(0.32g)、ビス(ジターシャリーブチル(4-ジメチルアミノフェニル)ホスフィン)ジクロロパラジウム(0.035g)、1,2,4-トリメチルベンゼン(20mL)および水(2mL)をフラスコに入れ、窒素雰囲気下、還流温度で5時間撹拌した。反応液を室温まで冷却し水を加え、析出物をろ過した。加熱クロロホルムに溶解させたのちにセライト濾過し、さらにベンゾニトリルおよびピリジンで再結晶を行い精製したのち、昇華精製して目的物化合物(0.54g)を得た。
1H-NMR(CDCl3): 9.1(s,2H)、 8.9(d,2H)、 8.9~8.8(m,4H)、 8.7(dd,2H)、 7.9(dd,2H)、 7.8~7.7(m,4H).
<3,9-ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)スピロ[ベンゾ[a]フルオレン-11,9’-フルオレン]の合成>
特開2009-184993公報の記載に従って合成したスピロ[ベンゾ[a]フルオレン-11,9’-フルオレン]-3,9-ジイルビス(トリフルオロメタンスルホナート)(5.00g)、ビス(ピナコラート)ジボロン(4.60g)、酢酸カリウム(2.96g)、(1,1’-ビス(ジフェニルホスフィノ)フェロセン)パラジウム(II)ジクロリド・ジクロロメタン錯体(0.18g)、およびシクロペンチルメチルエーテル(50mL)をフラスコに入れ、窒素雰囲気下、還流温度で8時間撹拌した。反応液を室温まで冷却し水を加え、さらにトルエンを加えて分液抽出を行った。有機層を分離後、乾燥、濃縮し、活性炭ショートカラム(展開液:トルエン)を通したのち、濃縮してヘプタンで再沈することで目的物化合物(4.00g)を得た。
3,9-ビス(4,4,5,5-テトラメチル-1,3,2-ジオキサボロラン-2-イル)スピロ[ベンゾ[a]フルオレン-11,9’-フルオレン](3.07g)、4-ブロモ-3-シアノピリジン(2.00g)、炭酸カリウム(2.75g)、臭化テトラ-n-ブチルアンモニウム(0.32g)、ビス(ジターシャリーブチル(4-ジメチルアミノフェニル)ホスフィン)ジクロロパラジウム(0.11g)、1,2,4-トリメチルベンゼン(20mL)および水(2mL)をフラスコに入れ、窒素雰囲気下、還流温度で5時間撹拌した。反応液を室温まで冷却し水を加え、さらにトルエンを加えて分液抽出を行った。有機層を分離後、乾燥、濃縮し、NHシリカゲルカラム(展開液:トルエン/酢酸エチル=4/1(容量比))で精製したのち、昇華精製して目的物化合物(1.20g)を得た。
1H-NMR(CDCl3):8.7(d,1H)、 8.6(d,1H)、 8.2~8.0(m,6H)、 7.9(d,1H)、 7.7(m,3H)、 7.5(dd,1H)、 7.5(dt,2H)、 7.3(dd,1H)、 7.1(dt,2H)、 6.9(d,1H)、 6.9(d,1H)、 6.7(d,2H).
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置((株)昭和真空製)の基板ホルダーに固定し、HI-1を入れたモリブデン製蒸着用ボート、ILを入れたモリブデン製蒸着用ボート、HT-1を入れたモリブデン製蒸着用ボート、BHを入れたモリブデン製蒸着用ボート、BDを入れたモリブデン製蒸着用ボート、本願発明の化合物(1-1-2)を入れたモリブデン製蒸着用ボート、Liqを入れたモリブデン製蒸着用ボート、マグネシウムを入れたタングステン製蒸着用ボート、銀を入れたタングステン製蒸着用ボートを装着した。
化合物(1-1-2)を化合物(1-2-27)に代えた以外は実施例1の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.21V、外部量子効率は3.75%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は157時間であった。
化合物(1-1-2)を化合物(1-2-48)に代えた以外は実施例1の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.47V、外部量子効率は4.21%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は298時間であった。
化合物(1-1-2)を化合物(1-2-173)に代えた以外は実施例1の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.30V、外部量子効率は7.20%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は312時間であった。
化合物(1-1-2)を化合物(1-2-179)に代えた以外は実施例1の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.20V、外部量子効率は4.96%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は292時間であった。
化合物(1-1-2)を化合物(1-2-506)に代えた以外は実施例1の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.23V、外部量子効率は4.75%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は303時間であった。
化合物(1-1-2)を化合物(A)に代えた以外は実施例1に準じた方法で有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は3.46V、外部量子効率は5.55%であった。また、また、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は169時間であった。
化合物(1-1-2)を化合物(B)に代えた以外は実施例1に準じた方法で有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は3.51V、外部量子効率は5.24%であった。また、また、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は77時間であった。
化合物(1-1-2)を化合物(C)に代えた以外は実施例1に準じた方法で有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は3.97V、外部量子効率は5.93%であった。また、また、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は145時間であった。
化合物(1-1-2)を化合物(D)に代えた以外は実施例1に準じた方法で有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は3.75V、外部量子効率は5.89%であった。また、また、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は116時間であった。
化合物(1-1-2)を化合物(E)に代えた以外は実施例1に準じた方法で有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は3.55V、外部量子効率は7.45%であった。また、また、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は155時間であった。
化合物(1-1-2)を化合物(F)に代えた以外は実施例1に準じた方法で有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.79V、外部量子効率は2.81%であった。また、また、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は122時間であった。
実施例1と同様の方法で発光層まで形成した後に、化合物(1-2-48)の入った蒸着用ボートを加熱して膜厚10nmになるように蒸着して電子輸送層を形成した。次いで、化合物(1-2-48)の入った蒸着用ボートとLiqの入った蒸着用ボートを同時に加熱して膜厚20nmになるように蒸着して電子注入層を形成した。化合物IとLiqの重量比がおよそ1対1になるように蒸着速度を調節した。各層の蒸着速度は0.01~1nm/秒であった。次いで実施例1と同様の方法でLiq層と陰極を形成して有機EL素子を得た。
化合物(1-2-48)を化合物(1-2-173)に代えた以外は実施例7の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は3.49V、外部量子効率は7.59%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は373時間であった。
化合物(1-2-48)を化合物(1-2-179)に代えた以外は実施例7の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.18V、外部量子効率は5.88%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は395時間であった。
化合物(1-2-48)を化合物(1-2-506)に代えた以外は実施例7の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.26V、外部量子効率は5.52%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は255時間であった。
化合物(1-2-48)を化合物Gに代えた以外は実施例7の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は4.02V、外部量子効率は5.79%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は202時間であった。
化合物(1-2-48)を化合物Hに代えた以外は実施例7の方法に準じて有機EL素子を得た。直流電圧を印加し、1000cd/m2発光時の特性を測定すると、駆動電圧は3.73V、外部量子効率は6.29%であり、1500cd/m2の輝度が得られる電流密度で定電流駆動試験を実施した結果、初期輝度の80%(1200cd/m2)以上の輝度を保持した時間は172時間であった。
Claims (13)
- 下記式(1)で表される化合物;
mは1~4の整数であり、mが2、3または4であるとき、ピリジン環とLで形成される基は同一でもよく、異なっていてもよく;
Lは単結合または下記式(L-1)および(L-2)で表される2価の基の群から選ばれる1つであり、
式(L-2)中、X7~X14は独立して=CR1-または=N-であり、X7~X14の内の少なくとも2つは=CR1-であり、X7~X14の内の2つの=CR1-におけるR1はArまたはピリジン環と結合する結合手であり、それ以外の=CR1-におけるR1は水素であり、
Lの少なくとも1つの水素は炭素数1~4のアルキルまたは炭素数6~18のアリールで置き換えられていてもよく;
ピリジン環の少なくとも1つの水素は炭素数1~4のアルキル、フェニルまたはナフチルで置き換えられていてもよく;そして、
式(1)中の各々の環およびアルキルの少なくとも1つの水素は重水素で置き換えられていてもよい。 - 式(1)中、Arが下記式(Ar1-1)~(Ar1-12)、(Ar2-1)~(Ar2-21)、(Ar3-1)、(Ar3-2)、および(Ar4-1)で表される基の群から選ばれる1つである、請求項1に記載の化合物;
- 式(1)中、Arが下記式(Ar1-1)~(Ar1-7)、(Ar2-1)、(Ar2-3)、(Ar2-6)~(Ar2-10)、(Ar2-12)、(Ar-2-21)、(Ar3-1)、および(Ar3-2)で表される基の群から選ばれる1つである、請求項1に記載の化合物;
- 請求項1~8のいずれか1項に記載の化合物を含有する電子輸送材料。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置される発光層と、前記陰極と該発光層との間に配置され、請求項9に記載の電子輸送材料を含有する電子輸送層および/または電子注入層とを有する有機電界発光素子。
- 陽極および陰極からなる一対の電極と、該一対の電極間に配置される発光層と、前記陰極と該発光層との間に配置され、請求項9に記載の電子輸送材料を含有する、電子輸送層および電子注入層を有する有機電界発光素子。
- 前記電子輸送層および電子注入層の少なくとも1つが、さらに、キノリノール系金属錯体、ビピリジン誘導体、フェナントロリン誘導体およびボラン誘導体からなる群から選択される少なくとも1つを含有する、請求項10または11に記載する有機電界発光素子。
- 電子輸送層および電子注入層の少なくとも1つが、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、請求項10~12のいずれか1項に記載の有機電界発光素子。
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Citations (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007029696A1 (ja) * | 2005-09-05 | 2007-03-15 | Chisso Corporation | 電子輸送材料およびこれを用いた有機電界発光素子 |
JP2008524121A (ja) * | 2004-12-17 | 2008-07-10 | メルク フロスト カナダ リミテツド | mPGES−1阻害剤としての2−(フェニルまたはヘテロ環式)−1H−フェナントロ[9,10−d]イミダゾール |
JP2008528576A (ja) * | 2005-01-31 | 2008-07-31 | グレイセル ディスプレイ インク. | 高発光効率の赤色リン光材料及びこれを含有している表示素子 |
CN101412907A (zh) * | 2007-10-17 | 2009-04-22 | 中国科学院理化技术研究所 | 有机电致发光材料及其合成方法和用途 |
US20090102356A1 (en) * | 2007-10-17 | 2009-04-23 | Technical Institute Of Physics And Chemistry Of Chinese Academy Of Sciences | NOVEL ORGANIC COMPOUND HAVING ELECTRON-TRANSPORTING AND/OR HOLE-BLOCKING PERFORMANCE AND ITS USE AND OLEDs COMPRISING THE COMPOUND |
JP2009173642A (ja) * | 2007-12-27 | 2009-08-06 | Chisso Corp | ピリジルフェニル基を有するアントラセン誘導体化合物及び有機電界発光素子 |
WO2010137678A1 (ja) * | 2009-05-29 | 2010-12-02 | チッソ株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
WO2011105373A1 (ja) * | 2010-02-25 | 2011-09-01 | 保土谷化学工業株式会社 | 置換されたピリジル化合物および有機エレクトロルミネッセンス素子 |
WO2012017680A1 (ja) * | 2010-08-05 | 2012-02-09 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
CN102491968A (zh) * | 2011-12-08 | 2012-06-13 | 大连理工大学 | 一种在水相中制备咔唑基联芳类化合物的方法 |
WO2013129491A1 (ja) * | 2012-02-29 | 2013-09-06 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子 |
WO2013175789A1 (ja) * | 2012-05-24 | 2013-11-28 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2014072407A (ja) * | 2012-09-28 | 2014-04-21 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子 |
KR20140060247A (ko) * | 2012-11-09 | 2014-05-19 | 희성소재 (주) | 유기발광소자 |
JP2014096572A (ja) * | 2012-10-11 | 2014-05-22 | Tdk Corp | 電界発光素子 |
JP2014175390A (ja) * | 2013-03-07 | 2014-09-22 | Tdk Corp | 芳香族化合物およびそれを用いた電界発光素子 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60100187T2 (de) | 2000-09-07 | 2004-04-01 | Chisso Corp. | Organische Elektrolumineszenzanordung mit einem Dipyridylthiophenderivat |
JP4172172B2 (ja) | 2001-10-10 | 2008-10-29 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子 |
DE102004062071A1 (de) | 2004-12-23 | 2006-07-06 | Schaeffler Kg | Nockenwellenversteller für eine Brennkraftmaschine |
KR100833857B1 (ko) * | 2005-05-31 | 2008-06-02 | 엘지전자 주식회사 | 세탁 장치 |
KR20130012431A (ko) * | 2011-07-25 | 2013-02-04 | 삼성전자주식회사 | 광 다이오드 및 이를 포함하는 광 센서 |
-
2015
- 2015-03-16 KR KR1020167016362A patent/KR102298990B1/ko active IP Right Grant
- 2015-03-16 JP JP2016508708A patent/JP6428762B2/ja active Active
- 2015-03-16 US US15/124,671 patent/US20170033293A1/en not_active Abandoned
- 2015-03-16 WO PCT/JP2015/057617 patent/WO2015141608A1/ja active Application Filing
- 2015-03-17 TW TW104108395A patent/TWI656118B/zh active
Patent Citations (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008524121A (ja) * | 2004-12-17 | 2008-07-10 | メルク フロスト カナダ リミテツド | mPGES−1阻害剤としての2−(フェニルまたはヘテロ環式)−1H−フェナントロ[9,10−d]イミダゾール |
JP2008528576A (ja) * | 2005-01-31 | 2008-07-31 | グレイセル ディスプレイ インク. | 高発光効率の赤色リン光材料及びこれを含有している表示素子 |
WO2007029696A1 (ja) * | 2005-09-05 | 2007-03-15 | Chisso Corporation | 電子輸送材料およびこれを用いた有機電界発光素子 |
CN101412907A (zh) * | 2007-10-17 | 2009-04-22 | 中国科学院理化技术研究所 | 有机电致发光材料及其合成方法和用途 |
US20090102356A1 (en) * | 2007-10-17 | 2009-04-23 | Technical Institute Of Physics And Chemistry Of Chinese Academy Of Sciences | NOVEL ORGANIC COMPOUND HAVING ELECTRON-TRANSPORTING AND/OR HOLE-BLOCKING PERFORMANCE AND ITS USE AND OLEDs COMPRISING THE COMPOUND |
JP2009173642A (ja) * | 2007-12-27 | 2009-08-06 | Chisso Corp | ピリジルフェニル基を有するアントラセン誘導体化合物及び有機電界発光素子 |
WO2010137678A1 (ja) * | 2009-05-29 | 2010-12-02 | チッソ株式会社 | 電子輸送材料およびこれを用いた有機電界発光素子 |
WO2011105373A1 (ja) * | 2010-02-25 | 2011-09-01 | 保土谷化学工業株式会社 | 置換されたピリジル化合物および有機エレクトロルミネッセンス素子 |
WO2012017680A1 (ja) * | 2010-08-05 | 2012-02-09 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
CN102491968A (zh) * | 2011-12-08 | 2012-06-13 | 大连理工大学 | 一种在水相中制备咔唑基联芳类化合物的方法 |
WO2013129491A1 (ja) * | 2012-02-29 | 2013-09-06 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子 |
WO2013175789A1 (ja) * | 2012-05-24 | 2013-11-28 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2014072407A (ja) * | 2012-09-28 | 2014-04-21 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子用材料、及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2014096572A (ja) * | 2012-10-11 | 2014-05-22 | Tdk Corp | 電界発光素子 |
KR20140060247A (ko) * | 2012-11-09 | 2014-05-19 | 희성소재 (주) | 유기발광소자 |
JP2014175390A (ja) * | 2013-03-07 | 2014-09-22 | Tdk Corp | 芳香族化合物およびそれを用いた電界発光素子 |
Non-Patent Citations (5)
Title |
---|
HAN,F-S. ET AL., TETRAHEDRON, vol. 64, 2008, pages 9108 - 9116 * |
HERBICH,J. ET AL., CHEMICAL PHYSICS LETTERS, vol. 262, 1996, pages 633 - 642 * |
MARCHALIN,S. ET AL., COLLECTION CZECHOSLOVAK CHEM. COMMUN., vol. 50, 1985, pages 1870 - 1877 * |
MARCHALIN,S. ET AL., COLLECTION CZECHOSLOVAK CHEM. COMMUN., vol. 51, 1986, pages 1061 - 1070 * |
PALKOVITS,R. ET AL., ANGEWANDTE CHEMIE, vol. 48, 2009, pages 6909 - 6912 * |
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