TWI675903B - 有機電致發光材料及其使用 - Google Patents
有機電致發光材料及其使用 Download PDFInfo
- Publication number
- TWI675903B TWI675903B TW106133581A TW106133581A TWI675903B TW I675903 B TWI675903 B TW I675903B TW 106133581 A TW106133581 A TW 106133581A TW 106133581 A TW106133581 A TW 106133581A TW I675903 B TWI675903 B TW I675903B
- Authority
- TW
- Taiwan
- Prior art keywords
- substituted
- unsubstituted
- carbon atoms
- group
- formula
- Prior art date
Links
- 0 *c(nc12)c(C#N)nc1c1nc(C#N)c(C#N)nc1c(nc1C#N)c2nc1C#N Chemical compound *c(nc12)c(C#N)nc1c1nc(C#N)c(C#N)nc1c(nc1C#N)c2nc1C#N 0.000 description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N c1ccc2c3ccccc3c(cccc3)c3c2c1 Chemical compound c1ccc2c3ccccc3c(cccc3)c3c2c1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 3
- RCGLUPXFJSDVBS-UHFFFAOYSA-N C(Cc(c(-c1c2)c3)ccc3-c(cc3)cc(c4ccccc44)c3[n]4-c3ccccc3)C(c3ccccc3)c1ccc2N1c(cc(c(c2c3)c4)[s]c2cc2c3c3ccccc3c3ccccc23)c4Sc2ccccc12 Chemical compound C(Cc(c(-c1c2)c3)ccc3-c(cc3)cc(c4ccccc44)c3[n]4-c3ccccc3)C(c3ccccc3)c1ccc2N1c(cc(c(c2c3)c4)[s]c2cc2c3c3ccccc3c3ccccc23)c4Sc2ccccc12 RCGLUPXFJSDVBS-UHFFFAOYSA-N 0.000 description 1
- OFJLZHQFIPOJPQ-UHFFFAOYSA-N C(Cc(c(-c1c2)c3)ccc3-c(cc3c4c5cccc4)ccc3[n]5-c3ccccc3)C(c3ccccc3)c1ccc2N1c(cc(c(c2c3cc(c4ccccc4c4ccccc44)c4c2)c2)[n]3-c3ccccc3)c2Sc2c1cccc2 Chemical compound C(Cc(c(-c1c2)c3)ccc3-c(cc3c4c5cccc4)ccc3[n]5-c3ccccc3)C(c3ccccc3)c1ccc2N1c(cc(c(c2c3cc(c4ccccc4c4ccccc44)c4c2)c2)[n]3-c3ccccc3)c2Sc2c1cccc2 OFJLZHQFIPOJPQ-UHFFFAOYSA-N 0.000 description 1
- KKBJUUCYWUUDNL-UHFFFAOYSA-N CC(C)(C)c1c(c2ccccc2c(c2c3)cc(C(C)(C)c4c5)c3-c4cc(Sc3cc(cccc4)c4cc33)c5N3c3nc(-c4c(cccc5)c5ccc4)nc(-c4c(cccc5)c5ccc4)n3)c2ccc1 Chemical compound CC(C)(C)c1c(c2ccccc2c(c2c3)cc(C(C)(C)c4c5)c3-c4cc(Sc3cc(cccc4)c4cc33)c5N3c3nc(-c4c(cccc5)c5ccc4)nc(-c4c(cccc5)c5ccc4)n3)c2ccc1 KKBJUUCYWUUDNL-UHFFFAOYSA-N 0.000 description 1
- KQYUQGDVVGJCCD-UHFFFAOYSA-N CC(C)(c(c1c2)cc3c2[o]c2c3cc(c(cccc3)c3c3ccccc33)c3c2)c2cc3ccccc3cc2N1c1nc(C(F)(F)F)nc(C(F)(F)F)n1 Chemical compound CC(C)(c(c1c2)cc3c2[o]c2c3cc(c(cccc3)c3c3ccccc33)c3c2)c2cc3ccccc3cc2N1c1nc(C(F)(F)F)nc(C(F)(F)F)n1 KQYUQGDVVGJCCD-UHFFFAOYSA-N 0.000 description 1
- GESWKLPDRNZBDF-UHFFFAOYSA-N CC(C)(c(c1c2)cc3c2[s]c2c3cc(c3ccccc3c3ccccc33)c3c2)c2cc3ccccc3cc2N1c1nc(C(F)(F)F)nc(C(F)(F)F)n1 Chemical compound CC(C)(c(c1c2)cc3c2[s]c2c3cc(c3ccccc3c3ccccc33)c3c2)c2cc3ccccc3cc2N1c1nc(C(F)(F)F)nc(C(F)(F)F)n1 GESWKLPDRNZBDF-UHFFFAOYSA-N 0.000 description 1
- GMSXUKPKCOJNPM-UHFFFAOYSA-N CC(C)(c(cc(c(cccc1)c1c1ccccc11)c1c1)c1-c1c2)c1cc1c2Sc2cc(cccc3)c3cc2N1c1cccc(-[n]2c(c(C3(C)C)c(cc4)-c5c3cccc5)c4c3c2cccc3)c1 Chemical compound CC(C)(c(cc(c(cccc1)c1c1ccccc11)c1c1)c1-c1c2)c1cc1c2Sc2cc(cccc3)c3cc2N1c1cccc(-[n]2c(c(C3(C)C)c(cc4)-c5c3cccc5)c4c3c2cccc3)c1 GMSXUKPKCOJNPM-UHFFFAOYSA-N 0.000 description 1
- YDALSYIKUQMEOX-UHFFFAOYSA-N CC(C)(c(cc(c1ccc(C)cc1c1c2cccc1)c2c1)c1-c1c2)c1cc1c2Oc2cc(cccc3)c3cc2N1c1cccc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c1 Chemical compound CC(C)(c(cc(c1ccc(C)cc1c1c2cccc1)c2c1)c1-c1c2)c1cc1c2Oc2cc(cccc3)c3cc2N1c1cccc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c1 YDALSYIKUQMEOX-UHFFFAOYSA-N 0.000 description 1
- YVVLZTHPPSCVED-UHFFFAOYSA-N CC(C)(c(cc(c1ccccc1c1c2cccc1)c2c1)c1-c1c2)c1cc1c2Oc2cc(cccc3)c3cc2N1c(cc1c2cc(-c(cc3c4c5cccc4)ccc3[n]5-c3ccccc3)ccc22)ccc1[n]2-c1ccccc1 Chemical compound CC(C)(c(cc(c1ccccc1c1c2cccc1)c2c1)c1-c1c2)c1cc1c2Oc2cc(cccc3)c3cc2N1c(cc1c2cc(-c(cc3c4c5cccc4)ccc3[n]5-c3ccccc3)ccc22)ccc1[n]2-c1ccccc1 YVVLZTHPPSCVED-UHFFFAOYSA-N 0.000 description 1
- ZAGZXNSLDHLNTI-UHFFFAOYSA-N CC(C)(c(cc(c1ccccc1c1c2cccc1)c2c1)c1-c1c2)c1cc1c2Sc2ccccc2N1c1cccc(-[n]2c(c(C3(C)C)c(cc4)-c5c3cccc5)c4c3c2cccc3)c1 Chemical compound CC(C)(c(cc(c1ccccc1c1c2cccc1)c2c1)c1-c1c2)c1cc1c2Sc2ccccc2N1c1cccc(-[n]2c(c(C3(C)C)c(cc4)-c5c3cccc5)c4c3c2cccc3)c1 ZAGZXNSLDHLNTI-UHFFFAOYSA-N 0.000 description 1
- XVJRZHZWFJMYDP-UHFFFAOYSA-N CC(C)(c(cc(c1ccccc1c1ccccc11)c1c1)c1-c1c2)c1cc1c2Oc(cc(cccc2)c2c2)c2N1c1cccc(-[n](c2ccccc2c2c3)c2cc2c3c(cccc3)c3[s]2)c1 Chemical compound CC(C)(c(cc(c1ccccc1c1ccccc11)c1c1)c1-c1c2)c1cc1c2Oc(cc(cccc2)c2c2)c2N1c1cccc(-[n](c2ccccc2c2c3)c2cc2c3c(cccc3)c3[s]2)c1 XVJRZHZWFJMYDP-UHFFFAOYSA-N 0.000 description 1
- NGZYVIGIQXQIOK-UHFFFAOYSA-N CC(C)(c(cc(c1ccccc1c1ccccc11)c1c1)c1-c1c2)c1cc1c2Oc(cccc2)c2N1c1cccc(-[n](c(cccc2)c2c2c3)c2cc2c3c3ccccc3[s]2)c1 Chemical compound CC(C)(c(cc(c1ccccc1c1ccccc11)c1c1)c1-c1c2)c1cc1c2Oc(cccc2)c2N1c1cccc(-[n](c(cccc2)c2c2c3)c2cc2c3c3ccccc3[s]2)c1 NGZYVIGIQXQIOK-UHFFFAOYSA-N 0.000 description 1
- GPHFXHZYAFEHGK-UHFFFAOYSA-N CC(C)(c(cc(c1ccccc1c1ccccc11)c1c1)c1-c1c2)c1cc1c2Sc2ccccc2N1c1nc(-c2c(cccc3)c3ccc2)nc(-c2c(cccc3)c3ccc2)n1 Chemical compound CC(C)(c(cc(c1ccccc1c1ccccc11)c1c1)c1-c1c2)c1cc1c2Sc2ccccc2N1c1nc(-c2c(cccc3)c3ccc2)nc(-c2c(cccc3)c3ccc2)n1 GPHFXHZYAFEHGK-UHFFFAOYSA-N 0.000 description 1
- ZNUSPXHIROOSSA-UHFFFAOYSA-N CC(C)(c(cc(cccc1)c1c1)c1Nc(cc1C2(C)C)ccc1-c1c2cc(c2ccccc2c2c3cccc2)c3c1)O Chemical compound CC(C)(c(cc(cccc1)c1c1)c1Nc(cc1C2(C)C)ccc1-c1c2cc(c2ccccc2c2c3cccc2)c3c1)O ZNUSPXHIROOSSA-UHFFFAOYSA-N 0.000 description 1
- WAWVHULHVZZMHA-UHFFFAOYSA-N CC(C)(c(cccc1)c1N(c1c2)c3nc(C(F)(F)F)nc(C(F)(F)F)n3)c1cc1c2[o]c2c1cc(c1ccccc1c1ccccc11)c1c2 Chemical compound CC(C)(c(cccc1)c1N(c1c2)c3nc(C(F)(F)F)nc(C(F)(F)F)n3)c1cc1c2[o]c2c1cc(c1ccccc1c1ccccc11)c1c2 WAWVHULHVZZMHA-UHFFFAOYSA-N 0.000 description 1
- IBFTZISMLAYVMC-UHFFFAOYSA-N CC(C)(c(cccc1)c1N(c1c2)c3nc(C(F)(F)F)nc(C(F)(F)F)n3)c1cc1c2[s]c2c1cc(c1ccccc1c1c3cccc1)c3c2 Chemical compound CC(C)(c(cccc1)c1N(c1c2)c3nc(C(F)(F)F)nc(C(F)(F)F)n3)c1cc1c2[s]c2c1cc(c1ccccc1c1c3cccc1)c3c2 IBFTZISMLAYVMC-UHFFFAOYSA-N 0.000 description 1
- GYFXRRFNTUADBD-UHFFFAOYSA-N CC(C)(c(cccc1)c1N(c1cccc(-c2nc(C#N)nc(C#N)n2)c1)c1c2)c1cc(c1c3)c2[o]c1cc1c3c2ccccc2c2c1cccc2 Chemical compound CC(C)(c(cccc1)c1N(c1cccc(-c2nc(C#N)nc(C#N)n2)c1)c1c2)c1cc(c1c3)c2[o]c1cc1c3c2ccccc2c2c1cccc2 GYFXRRFNTUADBD-UHFFFAOYSA-N 0.000 description 1
- MNTGSPAXPUYAPN-UHFFFAOYSA-N CC(C)(c(cccc1)c1N(c1cccc(-c2nc(C#N)nc(C#N)n2)c1)c1c2)c1cc1c2[s]c2c1cc(c1ccccc1c1ccccc11)c1c2 Chemical compound CC(C)(c(cccc1)c1N(c1cccc(-c2nc(C#N)nc(C#N)n2)c1)c1c2)c1cc1c2[s]c2c1cc(c1ccccc1c1ccccc11)c1c2 MNTGSPAXPUYAPN-UHFFFAOYSA-N 0.000 description 1
- RXRWHQBNPJCBGW-UHFFFAOYSA-N CC(C)(c1c2)c(cc(c3ccccc3c3ccccc33)c3c3)c3-c1ccc2Nc(cc(cccc1)c1c1)c1C(OC)=O Chemical compound CC(C)(c1c2)c(cc(c3ccccc3c3ccccc33)c3c3)c3-c1ccc2Nc(cc(cccc1)c1c1)c1C(OC)=O RXRWHQBNPJCBGW-UHFFFAOYSA-N 0.000 description 1
- YURPMUUZVXERJY-UHFFFAOYSA-N CC(C)(c1c2)c3cc(N(c4cc5ccccc5cc4C4(C)C)c5nc(F)nc(F)n5)c4cc3-c1cc1c2c2ccccc2c2ccccc12 Chemical compound CC(C)(c1c2)c3cc(N(c4cc5ccccc5cc4C4(C)C)c5nc(F)nc(F)n5)c4cc3-c1cc1c2c2ccccc2c2ccccc12 YURPMUUZVXERJY-UHFFFAOYSA-N 0.000 description 1
- DLNLWWVIKNSDJM-UHFFFAOYSA-N CC1(C)c(ccc(-[n](c(c(c2c3)c4)cc5c4c4ccccc4c4ccccc54)c2cc2c3Oc3ccccc3N2c2cccc(-[n]3c4ccccc4c4c3cccc4)c2)c2)c2N(c2ccccc2)c2c1cccc2 Chemical compound CC1(C)c(ccc(-[n](c(c(c2c3)c4)cc5c4c4ccccc4c4ccccc54)c2cc2c3Oc3ccccc3N2c2cccc(-[n]3c4ccccc4c4c3cccc4)c2)c2)c2N(c2ccccc2)c2c1cccc2 DLNLWWVIKNSDJM-UHFFFAOYSA-N 0.000 description 1
- KAKPRIAGMOCTQC-UHFFFAOYSA-N CC1(C)c(ccc(-[n](c2c3)c(cc4N(c5cc(-[n]6c(cccc7)c7c7c6cccc7)ccc5)c(cc(cccc5)c5c5)c5Oc4c4)c4c2cc2c3c3ccccc3c3ccccc23)c2)c2N(c2ccccc2)c2c1cccc2 Chemical compound CC1(C)c(ccc(-[n](c2c3)c(cc4N(c5cc(-[n]6c(cccc7)c7c7c6cccc7)ccc5)c(cc(cccc5)c5c5)c5Oc4c4)c4c2cc2c3c3ccccc3c3ccccc23)c2)c2N(c2ccccc2)c2c1cccc2 KAKPRIAGMOCTQC-UHFFFAOYSA-N 0.000 description 1
- MRWNYFZRWUXMEB-UHFFFAOYSA-N CC1(C)c2cc(Nc3nc(F)nc(F)n3)c(C(c3ccccc3)(c3ccccc3)c3cc(cccc4)c4cc3C)cc2-c2c1cc(c1ccccc1c1ccccc11)c1c2 Chemical compound CC1(C)c2cc(Nc3nc(F)nc(F)n3)c(C(c3ccccc3)(c3ccccc3)c3cc(cccc4)c4cc3C)cc2-c2c1cc(c1ccccc1c1ccccc11)c1c2 MRWNYFZRWUXMEB-UHFFFAOYSA-N 0.000 description 1
- AAWAHDVNVKOWKO-UHFFFAOYSA-N CCCc1nc(N(c2c(C(C)(C)c3c4)cccc2)c3cc(C2(C)C)c4-c3c2cc(c2ccccc2c2ccccc22)c2c3)nc(F)n1 Chemical compound CCCc1nc(N(c2c(C(C)(C)c3c4)cccc2)c3cc(C2(C)C)c4-c3c2cc(c2ccccc2c2ccccc22)c2c3)nc(F)n1 AAWAHDVNVKOWKO-UHFFFAOYSA-N 0.000 description 1
- CQQXZXYOGOMUQC-UHFFFAOYSA-N FC(c1nc(N2c(cc(cccc3)c3c3)c3Oc3c2cc2[s]c(cc(c4ccccc4c4ccccc44)c4c4)c4c2c3)nc(C(F)(F)F)n1)(F)F Chemical compound FC(c1nc(N2c(cc(cccc3)c3c3)c3Oc3c2cc2[s]c(cc(c4ccccc4c4ccccc44)c4c4)c4c2c3)nc(C(F)(F)F)n1)(F)F CQQXZXYOGOMUQC-UHFFFAOYSA-N 0.000 description 1
- YNBVOEVXRCYBTD-UHFFFAOYSA-N FC(c1nc(N2c(cc(cccc3)c3c3)c3Sc(cc3c4c5)c2cc3[o]c4cc2c5c3ccccc3c3ccccc23)nc(C(F)(F)F)n1)(F)F Chemical compound FC(c1nc(N2c(cc(cccc3)c3c3)c3Sc(cc3c4c5)c2cc3[o]c4cc2c5c3ccccc3c3ccccc23)nc(C(F)(F)F)n1)(F)F YNBVOEVXRCYBTD-UHFFFAOYSA-N 0.000 description 1
- KXDPWDCMUWCYPR-UHFFFAOYSA-N FC(c1nc(N2c(cc3[o]c(cc(c4ccccc4c4c5cccc4)c5c4)c4c3c3)c3Sc3c2cccc3)nc(C(F)(F)F)n1)(F)F Chemical compound FC(c1nc(N2c(cc3[o]c(cc(c4ccccc4c4c5cccc4)c5c4)c4c3c3)c3Sc3c2cccc3)nc(C(F)(F)F)n1)(F)F KXDPWDCMUWCYPR-UHFFFAOYSA-N 0.000 description 1
- MBIFEYYARLFISA-UHFFFAOYSA-N FC(c1nc(N2c(cc3[s]c(cc(c4ccccc4c4ccccc44)c4c4)c4c3c3)c3Oc3c2cccc3)nc(C(F)(F)F)n1)(F)F Chemical compound FC(c1nc(N2c(cc3[s]c(cc(c4ccccc4c4ccccc44)c4c4)c4c3c3)c3Oc3c2cccc3)nc(C(F)(F)F)n1)(F)F MBIFEYYARLFISA-UHFFFAOYSA-N 0.000 description 1
- MWDDGROQHRYUQX-UHFFFAOYSA-N N#Cc1nc(C#N)nc(-c2cc(N(c(cccc3)c3C(c3c4)=O)c3cc([s]c3c5)c4c3cc3c5c4ccccc4c4ccccc34)ccc2)n1 Chemical compound N#Cc1nc(C#N)nc(-c2cc(N(c(cccc3)c3C(c3c4)=O)c3cc([s]c3c5)c4c3cc3c5c4ccccc4c4ccccc34)ccc2)n1 MWDDGROQHRYUQX-UHFFFAOYSA-N 0.000 description 1
- QWXUYITUBFSFHP-UHFFFAOYSA-N N#Cc1nc(C#N)nc(-c2cccc(N(c(c3c4)cc5c4c(cc(c(cccc4)c4c4ccccc44)c4c4)c4[s]5)c4cc5ccccc5cc4C3=O)c2)n1 Chemical compound N#Cc1nc(C#N)nc(-c2cccc(N(c(c3c4)cc5c4c(cc(c(cccc4)c4c4ccccc44)c4c4)c4[s]5)c4cc5ccccc5cc4C3=O)c2)n1 QWXUYITUBFSFHP-UHFFFAOYSA-N 0.000 description 1
- XBBOPRDTPJIDSU-UHFFFAOYSA-N N#Cc1nc(C#N)nc(-c2cccc(N3c(cc4[o]c(cc(c5ccccc5c5ccccc55)c5c5)c5c4c4)c4Oc4c3cccc4)c2)n1 Chemical compound N#Cc1nc(C#N)nc(-c2cccc(N3c(cc4[o]c(cc(c5ccccc5c5ccccc55)c5c5)c5c4c4)c4Oc4c3cccc4)c2)n1 XBBOPRDTPJIDSU-UHFFFAOYSA-N 0.000 description 1
- NEYNNTNXPGLVKP-UHFFFAOYSA-N O=C(c(cccc1)c1N(c1cccc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c1)c1c2)c1cc(c1c3cc(c4ccccc4c4ccccc44)c4c1)c2[n]3-c1ccccc1 Chemical compound O=C(c(cccc1)c1N(c1cccc(-c2nc(-c3ccccc3)nc(-c3ccccc3)n2)c1)c1c2)c1cc(c1c3cc(c4ccccc4c4ccccc44)c4c1)c2[n]3-c1ccccc1 NEYNNTNXPGLVKP-UHFFFAOYSA-N 0.000 description 1
- QWAHJVSFUBUJQM-UHFFFAOYSA-N O=C1c2cc3ccccc3cc2N(c2cccc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c2)c2c1cc(c(cc(c1ccccc1c1ccccc11)c1c1)c1[n]1-c3ccccc3)c1c2 Chemical compound O=C1c2cc3ccccc3cc2N(c2cccc(-c3nc(-c4ccccc4)nc(-c4ccccc4)n3)c2)c2c1cc(c(cc(c1ccccc1c1ccccc11)c1c1)c1[n]1-c3ccccc3)c1c2 QWAHJVSFUBUJQM-UHFFFAOYSA-N 0.000 description 1
- TXZOUJSOMPLEAP-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(N2c(cc(c(c3c4cc(c(cccc5)c5c5ccccc55)c5c3)c3)[n]4-c4ccccc4)c3Oc3c2cccc3)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(N2c(cc(c(c3c4cc(c(cccc5)c5c5ccccc55)c5c3)c3)[n]4-c4ccccc4)c3Oc3c2cccc3)n1 TXZOUJSOMPLEAP-UHFFFAOYSA-N 0.000 description 1
- DMFIPLMDAJJOKQ-UHFFFAOYSA-N c(cc1)ccc1-c1nc(N2c(cc(cccc3)c3c3)c3Oc(cc3c4c5cc(c6ccccc6c6c7cccc6)c7c4)c2cc3[n]5-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound c(cc1)ccc1-c1nc(N2c(cc(cccc3)c3c3)c3Oc(cc3c4c5cc(c6ccccc6c6c7cccc6)c7c4)c2cc3[n]5-c2ccccc2)nc(-c2ccccc2)n1 DMFIPLMDAJJOKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/20—Delayed fluorescence emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/90—Multiple hosts in the emissive layer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
本發明提供一種用於有機電致發光(Organic Electroluminescence,以下簡稱為有機EL)裝置之具有式(1)或式(2)材料及有機EL裝置,該裝置使用該材料作為磷光發光主體、延遲螢光摻雜劑及電洞阻擋層(hole blocking layer,HBL)。
一般而言,有機EL裝置由位於兩個電極之間的有機材料層組成,有機材料層包括電洞傳輸層(hole transport layer,HTL)、發光層(emitting layer,EML)、電子傳輸層(electron transport layer,ETL)。有機EL的基本機制包括載子的注入、載子傳輸、復合以及形成發光的激子。當外部電壓施加到有機EL裝置時,電子及電洞將分別自陰極及陽極注入,電子將從陰極注入最低未佔用分子軌域(lowest unoccupied molecular orbital,LUMO)中,且電洞將從陽極注入最高佔用分子軌域(highest occupied molecular orbital,HOMO)中。當電子與電洞在發光層中復合時,將會形成激子並隨後發光。當發光分子吸收能量以達到激發態時,根據電子及電洞自旋組合方式,而激子可處於單重態或三重態。透過重組電子及電洞形成75%的激子而達到三重激發態。從三重態的衰減為自旋禁阻,因
此,螢光電致發光裝置僅具有25%的內部量子效率。與螢光電致發光裝置相反,磷光有機EL裝置利用自旋軌域交互作用來促進單重態與三重態之間的系統間跨越,從而獲得單重態和三重態的發射以及從25%到100%的電致發光元件內部量子效率。自旋軌域交互作用由一些重原子完成,比如,銥、銠、鉑、鈀,且可從有機金屬複合物的激發金屬配位基電荷轉移(metal-to-ligand charge-transfer transition,MLCT)狀態來觀察磷光躍遷。
近來,安達(Adachi)及同事(2012年)已開發熱活化型延遲螢光(thermally activated delayed fluorescence,TADF)機制,並將其整合至新型螢光有機EL裝置,其透過在單重態及三重態間使用具有較小能量間隙的材料得到的逆向系統間跨越(reverse intersystem crossing,RISC)機制,將自旋禁阻的三重態激子轉化為單重態而獲得高效率的激子。然而,於高電流密度中仍需要進一步提高有機EL裝置的發光效率。
磷光有機EL利用三重態激子和單重態激子。由於與單重態激子相比,三重態激子的壽命更長且飄移距離更遠,磷光有機EL通常在發光層(EML)與電子傳輸層(ETL)之間需要附加電洞阻擋層(HBL),或需要具有電洞阻擋能力的電子傳輸層(HBETL)來替代一般的ETL。使用HBL或HBETL的目的是將注入的電洞與電子的復合以及所產生激子的弛豫侷限在EML內,藉此可提高裝置的效率。為了滿足該目標,電洞阻擋材料需具有適於阻擋電洞從EML向ETL傳輸及適於從ETL向EML傳送電子的最高佔用分子軌域(HOMO)及最低未佔用分子軌域(LUMO)能階,另外,還需要良好的材料熱穩定性及電化學穩定性。
對於主動矩陣有機發光二極體(active-matrix organic
light-emitting diode,AMOLED)或有機發光二極體(organic light-emitting diode,OLED)為發光面板的全彩平板顯示器來說,使用於發光層中磷光摻雜劑材料之半衰期、效率及驅動電壓方面仍無法令人滿意。這些有機金屬複合物對於產業實施的用途來說仍具有劣勢。由於減少了對外部發射無益的垂直發射偶極比率,並且水平發射偶極的輻射模式通常較適於光輸出耦合,所以具有優先平面(水平)發光偶極的磷光摻雜劑對於OLED的光輸出耦合是有益的。因此,具有適當取代基的發射體可有助於提高OLED發射層中的水平發射偶極比率。同時,發射體周圍的適當取代基可有效地阻擋附近的電子及電洞,以便電子和電洞可輕易在發射體中重組,且可提高OLED的效率。
還需要能夠有效傳輸電子或電洞並阻擋電洞的有機EL材料,同時需要具有良好的熱穩定性及高發射效率的高效EML材料。根據上述原因,本發明之目的為解決現有技術的這些問題,並提供一種發光裝置,其在熱穩定性、高發光效率、高亮度及長半衰期上表現極佳。本發明揭露一種具有式(1)或式(2)的新穎材料,其用作磷光發光主體、延遲螢光摻雜劑及電洞阻擋層(HBL),該等層具有良好的電荷載子遷移率,且極佳的操作耐用性可降低有機EL裝置的驅動電壓和能耗、提高有機EL裝置的效率並延長其半衰期。
本發明提供一種可用作有機EL的磷光發光主體、延遲螢光摻雜劑及電洞阻擋層(HBL)的新穎材料及其用於有機EL裝置的用
途。該材料克服了習知材料的缺點,如半衰期較短、效率較低及能耗較高。
本發明的目的是提供可用作有機EL裝置的電洞阻擋層(HBL)材料及可有效限制激子傳輸至電子傳輸層的新穎材料。
本發明的目的是提供可用作有機EL裝置的磷光主體材料、發光層的延遲螢光摻雜劑並提高效率及延長半衰期的新穎材料。
6‧‧‧透明電極
7‧‧‧電洞注入層
8‧‧‧電洞傳輸層
9‧‧‧電子阻擋層
10‧‧‧發光層
11‧‧‧電洞阻擋層
12‧‧‧電子傳輸層
13‧‧‧電子注入層
14‧‧‧金屬電極
圖1係為本發明之用於有機電致發光裝置之延遲螢光化合物之實施例的有機EL裝置之示意圖。
本發明研究的是材料及使用該材料的有機EL裝置。下面將詳細說明生產、結構及組成部份,以使對本發明的理解更充分。本發明的應用顯然不受限於所屬技術領域具有通常知識者熟知的具體細節。另一方面,眾所周知的一般組成成分和程序不作詳細說明,以避免對本發明
造成不必要的限制。現在將在下面更詳細地介紹本發明的一些優選實施例。然而,應該瞭解,除了詳細描述的實施例之外,本發明還可實施於各式各樣的其他實施例中,也就是說,本發明還可廣泛地應用於其他實施例,且本發明的範圍沒有明確的限制,除隨附申請專利權利範圍限定的內容。
在本實施例中,一些材料表示為:
本發明中材料的詳細製備由示例性實施例闡明,但本發明不限於示例性實施例。實施例1至實施例6展示本發明中材料的一些實施例的製備。實施例7展示有機EL裝置的製作及有機EL裝置的I-V-B、半衰期測試報告。
實施例1
化合物5的合成
中間體A的合成
混合5.0g(11.8mmol)12-溴-10,10-二甲基-10氫-茚并[1,2-b]聯伸三苯(12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene)、2.0g(13.0mmol)2-胺基苯甲酸甲酯(2-aminobenzoate)、0.13g(0.59mmol)乙酸鈀(Pd(OAc)2)、0.17g(0.59mmol)四氟硼酸三叔丁基膦(tri-tert-but ylphosphonium tetrafluoroborate)、3.9g(17.7mmol)叔丁醇鈉(sodium tert-butoxide)、50ml甲苯(toluene),除氣並放置在氮氣中,隨後在110℃加熱16h。反應完成後,使混合物冷卻至室溫。有機層使用二氯甲烷(Dichloromethane,DCM)及水萃取,使用無水硫酸鎂(MgSO4)乾燥,移除溶劑並透過矽膠管柱層析法純化,得到產物(3.2g,產率:56%)。
中間體B的合成
在氮氣中,於無水四氫呋喃(Tetrahydrofuran,THF)
中攪拌3.2g(6.6mmol)中間體A,並緩慢滴入甲基溴化鎂(methyl magnesium bromide)(4.6當量)。在室溫下攪拌混合物16h。反應完成後,緩慢加入蒸餾水,使用乙酸乙酯(ethyl acetate)來萃取混合物,使用水來清洗。有機層使用二氯甲烷及水萃取,使用無水MgSO4乾燥,移除溶劑並透過矽膠管柱層析法純化,得到產物(1g,產率:32%)。
中間體C的合成
混合3g(6.0mmol)中間體B及過量的磷酸(phosphor ic acid)溶劑(100ml),在室溫下攪拌。攪拌混合物超過16h後,緩慢加入蒸餾水(100-150ml)。攪拌混合物0.5到1小時,過濾沉澱的固體。使用氫氧化鈉(sodium hydroxide)水溶液及二氯甲烷溶劑萃取過濾的固體,使用硫酸鎂從有機層中除去水分。隨後移除殘留溶劑,得到中間體C(2g,產率:72%)。MS(m/z,FAB+):475.6。
化合物5的合成
將中間體C(2g,4.2mmol)的二甲基甲醯胺(Dimethy lformamide,DMF)溶液(30ml)緩慢加入氫化鈉(NaH)(60%在油中)(0.84g,21.0mmol)的DMF溶液(30ml)中。在冰浴下,將2-氯-4,6-二苯基-1,3,5-三嗪(2.2g,8.4mmol)(2-chloro-4,6-diphenyl-1,3,5-triazine)加入混合物中,隨後在室溫下攪拌。30分鐘後,將反應混合物倒入水中,得到固體。所得固體使用昇華純化,得到化合物5(0.7g,產率:40%)。MS(m/z,FAB+):706.8
實施例2
化合物11的合成
混合2.0g(4.2mmol)中間體C、2.4g(6.3mmol)2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪(2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine)、0.07g(0.3mmol)Pd(OAc)2、0.09g(0.3mmol)四氟硼酸三叔丁基膦(tri-tert-butylphosphonium tetrafluoroborate)、0.9g(9.46mmol)叔丁醇鈉、50ml甲苯,除氣並放置在氮氣中,隨後在120℃加熱16h。反應完成後,使混合物冷卻至室溫。有機層使用二氯甲烷及水萃取,使用無水MgSO4乾燥,移除溶劑並透過矽膠管柱層析法純化,得到化合物11(1.9g,產率:55%)。MS(m/z,FAB+):783.0
實施例3
化合物17的合成
混合2.0g(4.2mmol)中間體C、3.5g(6.3mmol)6-溴-9,9’-二苯基-9氫,9’氫-3,3’-二咔唑(6-bromo-9,9’-diphenyl-9H,9’H-3,3’-bicarbazole)、0.07g(0.3mmol)Pd(OAc)2、0.09g(0.3mmol)四氟硼酸三叔丁基膦(tri-tert-butylphosphonium tetrafluoroborate)、0.9g(9.46mmol)叔丁醇鈉、50ml甲苯,除氣並放置在氮氣中,隨後在120℃加熱16h。反應完成後,使混合物冷卻至室溫。有機層使用二氯甲烷及水萃取,使用無水MgSO4乾燥,移除溶劑並透過矽膠管柱層析法純化,得到化合物17(1.9g,產率:48%)。MS(m/z,FAB+):957.8
中間體D的合成
混合5.0g(11.8mmol)12-溴-10,10-二甲基-10氫-茚并[1,2-b]聯伸三苯(12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene)、2.6g(13.0mmol)3-胺基-2-萘甲酸甲酯(methyl 3-amino-2-naphthoate)、0.13g(0.59mmol)Pd(OAc)2、0.17g(0.59mmol)四氟硼酸三叔丁基膦(tri-tert-butylphosphonium tetrafluoroborate)、3.9g(17.7mmol)叔丁醇鈉、80ml甲苯,除氣並放置在氮氣中,隨後在110℃加熱16h。反應完成後,使混合物冷卻至室溫。有機層使用二氯甲烷及水萃取,使用無水MgSO4乾燥,移除溶劑並透過矽膠管柱層析法純化,得到產物(3.2g,產率:51%)。
中間體E的合成
在氮氣中,於無水THF中攪拌3.2g(5.8mmol)中間體D,並緩慢滴入甲基溴化鎂(4.6當量)。在室溫下攪拌混合物16h。反應完成後,緩慢加入蒸餾水,使用乙酸乙酯來萃取混合物,使用水來清洗。有機層使用二氯甲烷及水萃取,使用無水MgSO4乾燥,移除溶劑並透過
矽膠管柱層析法純化,得到產物(1.1g,產率:36%)。
中間體F的合成
混合1.1g(2.1mmol)中間體E及過量的磷酸溶劑(66ml),在室溫下攪拌。攪拌混合物超過16h後,緩慢加入蒸餾水(~120ml)。攪拌混合物1小時,過濾沉澱的固體。使用氫氧化鈉水溶液及二氯甲烷溶劑萃取過濾的固體,使用硫酸鎂從有機層中除去水分。隨後移除殘留溶劑,得到中間體F(0.8g,產率:76%)。MS(m/z,FAB+):526.1
實施例4
化合物6的合成
將中間體F(1g,1.9mmol)的DMF溶液(30ml)緩慢加入NaH(60%在油中)(0.38g,9.8mmol)的DMF溶液(30ml)中。在
冰浴下,將2-氯-4,6-二苯基-1,3,5-三嗪(1.5g,5.7mmol)(2-chloro-4,6-diphenyl-1,3,5-triazine)加入混合物中,隨後在室溫下攪拌。30分鐘後,將反應混合物倒入水中,得到固體。所得固體使用昇華純化,得到化合物6(0.6g,產率:42%)。MS(m/z,FAB+):756.5
實施例5
化合物12的合成
混合2.2g(4.2mmol)中間體F、2.4g(6.3mmol)2-(3-溴苯基)-4,6-二苯基-1,3,5-三嗪(2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine)、0.07g(0.3mmol)Pd(OAc)2、0.09g(0.3mmol)四氟硼酸三叔丁基膦(tri-tert-butylphosphonium tetrafluoroborate)、0.9g(9.46mmol)叔丁醇鈉、50ml甲苯,除氣並放置在氮氣中,隨後在120℃加熱16h。反應完成後,使混合物冷卻至室溫。有機層使用二氯甲烷及水萃取,使用無水MgSO4除去水份,移除溶劑並透過矽膠管柱層析法純化,得到產物。所得固體使
用昇華純化,得到化合物12(1.6g,產率:48%)。MS(m/z,FAB+):832.9
實施例6
化合物18的合成
混合2.2g(4.2mmol)中間體F、3.5g(6.3mmol)6-溴-9,9’-二苯基-9氫,9’氫-3,3’-二咔唑(6-bromo-9,9’-diphenyl-9H,9’H-3,3’-bicarbazole)、0.07g(0.3mmol)Pd(OAc)2、0.09g(0.3mmol)四氟硼酸三叔丁基膦(tri-tert-butylphosphonium tetrafluoroborate)、0.9g(9.46mmol)叔丁醇鈉、50ml甲苯,除氣並放置在氮氣中,隨後在120℃加熱16h。反應完成後,使混合物冷卻至室溫。有機層使用二氯甲烷及水萃取,使用無水MgSO4乾燥,移除溶劑並透過矽膠管柱層析法純化,得到產物。所得固體使用昇華純化,得到化合物18(1.7g,產率:41%)。MS(m/z,FAB+):1007.9
延遲螢光化合物之光物理特性的測量方法
光物理特徵:合成的化合物在高真空下透過溫度梯度進行純化,隨後用在之後的研究中。透過在基礎壓力<10-6torr的真空室中以1-2A/sec的速率於石英基材上熱蒸發來製備用於檢測光物理特徵的薄膜。所得薄膜及稀釋溶液的吸收光譜由UV-vis-NIR分光光度儀(UV-1650 PC,Shimadzu)檢測。光激螢光(Photoluminescence,PL)光譜、冷光量子吸收量(photoluminescence quantum yields,PLQYs)及磷光光譜由螢光分光光度儀(FluoroMax-P,Horiba Jobin Yvon Inc.)檢測。薄膜或稀釋溶液的PLQYs使用配備校準積分球的該螢光分光光度儀來檢測。使用選定的單色激發光來激發位於校準積分球中的激發樣本。透過對比單色激發光及PL發射的光譜強度,測定PL量子吸收量。透過配有微秒閃光燈作為脈衝激發光源的螢光分光光度儀在77K(液氮溫度)下檢測薄膜或稀釋溶液的磷光光譜。在發射光譜的脈衝激發及收集之間插入10-ms延遲時間。透過使用具有螢光壽命系統(FluoroCube,Horiba Jobin Yvon Inc.)及來自UV發光二極體的奈秒脈衝光激發(300nm)的時間相關單光子計數技術監控PL峰值波長處的強度衰減來量測時間解析PL(PL衰減曲線)。將樣本放置在具有溫度控制的真空低溫恆溫室中。使用在發射光譜的脈衝激發與收集之間具有200-ns延遲時間及10-ns延遲時間的相同螢光壽命系統來收集PL光譜的瞬時成份及延遲成份。電化學特徵:使用CHI619B恆電位儀的循環伏安法來量測氧化/還原電位。透過使用0.1M n-Bu4NPF6(TBAPF6)在CH2Cl2中作為支持電解質,掃描速率為100mV s-1,藉由循環伏安法測定氧化電位。透過使用0.1M n-Bu4NClO4(TBAP)在DMF中作為支持電解質,掃描速率為100mVs-1,記錄還原電位。使用包含銀/氯化銀(Ag/AgCl)、
鉑金線及玻璃碳電極分別作為參考、計數及工作電極的標準3-電極電池。以Ag/AgCl(飽和)作為參考電極記錄所有電位。使用校準積分球測量系統以Ag/AgCl(飽和)收集總發射通量時,二茂鐵/二茂鐵離子(Fc/Fc+)氧化還原對在CH2Cl2/TBAPF6中的氧化發生於E’o=+0.47V,且二茂鐵/二茂鐵離子(Fc/Fc+)氧化還原對在DMF/TBAP中的還原發生於E”o=+0.51V。
生產有機EL裝置的一般方法
提供阻值為9~12歐姆/平方(ohm/square)及厚度為120~160nm的ITO塗層玻璃並在超音波浴(例如洗滌劑、去離子水)中進行多步驟清洗。在氣相沉積有機層之前,透過紫外光(UV)和臭氧進一步處理清洗後的ITO基板。ITO基板的所有預處理製程皆在潔淨室(100級)內進行。
透過高真空設備(10-7Torr)的氣相沉積將這些有機層依次塗佈於ITO基板上,比如:電阻加熱石英舟。每層的厚度和氣相沉積速率(0.1~0.3nm/sec)由石英晶體監視器來精確監控或設定。如上所述,還可以使單個層包含多於一種化合物,即通常是主體材料摻雜有摻雜材料。此可透過來自兩個或更多個來源的共蒸發來實現。
在該有機EL裝置中,使用二吡嗪并[2,3-f:2,3-]喹噁啉-2,3,6,7,10,11-六腈(dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitrile)(HAT-CN)作為電洞注入層,且N,N-二(萘-1-基)-N,N-雙(苯基)-聯苯胺(N,N-Bis(naphthalene-1-yl)-N,N-bis(phenyl)-benzidine)(NPB)廣泛用作電洞傳輸層,N-(聯苯-4-基)-9,9-二甲基-N-(4’-苯基聯苯-4-基)-9氫-茀-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4’-phenylbiphenyl-4-yl)-9H-fluoren-2-
amine)(EB2)用作電子阻擋層,且化學結構如下所示:
將1,3-二(9氫-咔唑-9-基)苯(1,3-di(9H-carbazol-9-yl)benzene)(mCP)用作發光層的延遲螢光主體並摻雜實施例1至實施例6用
於本發明的有機EL裝置。
有機銥複合物廣泛用作發光層的磷光摻雜劑,而Ir(ppy)3廣泛用作發光層的磷光摻雜劑,用於摻入本發明的磷光發光主體中。
HB3(參見下面的化學結構)用作電洞阻擋材料(HBM),且2-(10,10-二甲基-10氫-茚并[2,1-b]聯伸三苯-12-基)-4,6-二苯基-1,3,5-三嗪(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,6-diphenyl-1,3,5-triazine)(ET2)用作電子傳輸材料,以在有機EL裝置中與8-羥基喹啉-鋰(8-hydroxyquinolato-lithium)(LiQ)共沉積。本發明中用於製作標準有機EL裝置對照與比較材料的其他先前技術OLED材料之化學結構如下所示:
有機EL裝置一般包含透過熱蒸發作為陰極的低功函數金屬,比如,Al、Mg、Ca、Li及K,且該低功函數金屬可有助於電子從陰極注入電子傳輸層。另外,在陰極及電子傳輸層之間引入薄膜電子注入層,用於減少電子注入障礙並提高有機EL裝置性能。習知的電子注入層材料為具有低功函數的金屬鹵化物或金屬氧化物,比如:LiF、LiQ、MgO或Li2O。另一方面,在製作有機EL裝置之後,透過使用PR650光譜掃描光譜儀量測EL光譜及CIE座標。此外,電流/電壓、發光/電壓及產率/電壓特性都使用吉時利(Keithley)2400可編程電壓電流源來檢測。在室溫(約25℃)及大氣壓下操作上述設備。
實施例7
使用與上述一般方法類似的程序製作具有下列裝置結構的磷光發光有機EL裝置(參見圖1)。有機EL裝置包含透明電極6與金屬電極14,其間依序分別為沉積在透明電極6上的電洞注入層7、沉積在電洞注入層7上的電洞傳輸層8、沉積在電洞傳輸層8上的電子阻擋層9、沉積在電子阻擋層9上的發光層10、沉積在發光層10上的電洞阻擋層11、沉積在電洞阻擋層11上的電子傳輸層12、沉積在電子傳輸層12上的
電子注入層13,並且金屬電極14沉積在電子注入層13上。裝置:ITO/HAT-CN(20nm)/NPB(110nm)/EB2(5nm)/摻雜12%磷光發光摻雜劑的發光主體(30nm)/HBM(10nm)/ET2摻雜45%LiQ(35nm)/LiQ(1nm)/Al(160nm),而且製作具有下列裝置結構的延遲螢光裝置(參見圖1)。裝置:ITO/HAT-CN(20nm)/NPB(110nm)/EB2(5nm)/摻雜20%延遲螢光化合物的mCP(25nm)/HBM(10nm)/ET2摻雜45% LiQ(35nm)/LiQ(1nm)/Al(160nm)。(HBM=電洞阻擋材料)磷光發光有機EL裝置和延遲螢光裝置的I-V-B(於1000nits亮度時)和半衰期測試報告如表1所示。T70定義為3000cd/m2的初始亮度降至2100cd/m2的時間(小時)。
在上述較佳實施例的有機EL裝置測試報告(參見表1)中,我們證明了本發明中具有式(1)或式(2)的材料用作磷光發光主體及電洞阻擋材料展現出比先前技術的OLED材料更良好的性能。另外,用作延遲螢光摻雜劑的C5、C6和C11與mCP共沉積可表現出良好的效率,達到28cd/A。
鑒於上述教示顯然可以作出許多的修改及變化。因此,應該瞭解,在隨附申請專利範圍的範圍內,本發明可以除本文具體所述方式之外的其他方式來進行實踐。雖然,本文已示出並說明了具體實施例,
但對於所屬技術領域中具有通常知識者來說,可在不偏離旨在單獨由隨附申請專利範圍限制的那些情況下,對本發明作出許多修改。
Claims (14)
- 本發明專利申請範圍為:一種材料,其具有下列式(1)或式(2): 其中p表示0到8的整數,X分別表示選自由O、S、C(R2)(R3)、N(R4)及Si(R5)(R6)組成的原子或基團的二價橋,Z分別表示選自由C(R7)(R8)、N(R9)、Si(R10)(R11)及C=O組成的原子或基團的二價橋,Ar表示氫原子或稠合碳環;A選自由氫原子、具有6到60個碳原子的經取代或未經取代芳基、具有3到60個碳原子的經取代或未經取代雜芳基所組成之群組,且其中A表示經取代或未經取代的咔唑基、經取代或未經取代的雙咔唑基、經取代或未經取代的二苯并呋喃基、經取代或未經取代的二苯并噻吩基、經取代或未經取代的三嗪基、經取代或未經取代的二嗪基、經取代或未經取代的吡啶基、經取代或未經取代的喹啉基、經取代或未經取代的異喹啉基、經取代或未經取代的喹唑啉基、經取代或未經取代的啡啉基、經取代或未經取代的二氫吖啶基、經取代或未經取代的啡噻嗪基、經取代或未經取代的啡噁嗪基、及經取代或未經取代的二氫啡嗪基;R1至R11分別選自由氫原子、鹵化物、具有1到30個碳原子的經取代或未經取代烷基、具有6到30個碳原子的經取代或未經取代芳基、具有7到30個碳原子的經取代或未經取代芳烷基、及具有3到30個碳原子的經取代或未經取代雜芳基所組成之群組。
- 如申請專利範圍第1項所述之材料,其中該A由下式(3)至式(6)表示: 其中L1至L4表示單鍵、具有6到30個環碳原子的經取代或未經取代伸芳基(arylene)、或具有3到30個環碳原子的經取代或未經取代雜伸芳基(heteroarylene),m表示0到4的整數,n表示0或1的整數,Y1至Y3分別表示選自O、S、C(R17)(R18)、及N(R19)組成的原子或基團的二價橋,Z1至Z6表示氮原子或C(Rs),且各個Rs表示氫原子、苯基、具有1到30個碳原子的經取代或未經取代烷基、具有6到30個碳原子的經取代或未經取代芳基;R12至R19分別選自由氫原子、鹵化物、具有1到30個碳原子的經取代或未經取代烷基、具有6到30個碳原子的經取代或未經取代芳基、具有7到30個碳原子的經取代或未經取代芳烷基、及具有3到30個碳原子的經取代或未經取代雜芳基所組成之群組。
- 一種有機電致發光裝置,其包含由陰極及陽極組成的一電極對,且其中該電極對之間至少包含一發光層、一層或多層有機薄膜層,其中該發光層或該有機薄膜層包含如申請專利範圍第1項所述之材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中,包括具有式(1)或式(2)之該材料的該發光層為一磷光主體材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包括具有式(1)或式(2)之該材料的該發光層為一延遲螢光主體材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包括具有式(1)或式(2)之該材料的該發光層為一延遲螢光摻雜材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包括具有式(1)或式(2)之該材料的該有機薄膜層為一電洞阻擋材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中包括具有式(1)或式(2)之該材料的該有機薄膜層為一電子傳輸材料。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該發光層發射紅色磷光、藍色磷光、綠色磷光及黃色磷光。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該發光層發射紅色延遲螢光、藍色延遲螢光、綠色延遲螢光及黃色延遲螢光。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該裝置為一有機發光裝置。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該裝置為一發光面板。
- 如申請專利範圍第4項所述之有機電致發光裝置,其中該裝置為一背光面板。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/499,938 US10103337B1 (en) | 2017-04-28 | 2017-04-28 | Organic electroluminescent material and using the same |
US15/499,938 | 2017-04-28 |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201839092A TW201839092A (zh) | 2018-11-01 |
TWI675903B true TWI675903B (zh) | 2019-11-01 |
Family
ID=61104249
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW106133581A TWI675903B (zh) | 2017-04-28 | 2017-09-29 | 有機電致發光材料及其使用 |
Country Status (3)
Country | Link |
---|---|
US (1) | US10103337B1 (zh) |
CN (1) | CN107629068B (zh) |
TW (1) | TWI675903B (zh) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109369616A (zh) * | 2018-12-05 | 2019-02-22 | 武汉华星光电半导体显示技术有限公司 | 绿光热活化延迟荧光材料及其合成方法、电致发光器件 |
CN109659442B (zh) * | 2018-12-13 | 2022-04-26 | 云谷(固安)科技有限公司 | 一种有机电致发光器件和显示装置 |
US20200235306A1 (en) * | 2019-01-20 | 2020-07-23 | Luminescence Technology Corporation | Organic compound and organic electroluminescence device using the same |
US11276828B2 (en) * | 2019-01-21 | 2022-03-15 | Luminescence Technology Corp. | Organic compound and organic electroluminescence device using the same |
CN110016037B (zh) * | 2019-03-08 | 2021-10-22 | 中山大学 | 一种新型氮杂稠环化合物及其制备方法和应用 |
CN113512043A (zh) * | 2021-08-17 | 2021-10-19 | 浙江华显光电科技有限公司 | 有机化合物、制剂、有机发光器件和显示或照明装置 |
CN117069741B (zh) * | 2023-08-31 | 2023-12-26 | 东华大学 | 一种多态发光型热激活延迟荧光分子及其制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW201111469A (en) * | 2009-09-28 | 2011-04-01 | Ritdisplay Corp | Organic electroluminescence device |
US20140166988A1 (en) * | 2012-12-17 | 2014-06-19 | Luminescence Technology Corporation | Organic compound and organic electroluminescent device using the same |
CN105377822A (zh) * | 2013-07-10 | 2016-03-02 | 三星Sdi株式会社 | 有机组合物、有机光电子元件及显示装置 |
JP2016147846A (ja) * | 2015-01-07 | 2016-08-18 | 機光科技股▲分▼有限公司 | 有機エレクトロルミネセント装置用の化合物及びこの化合物を用いる有機エレクトロルミネセント装置 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9190619B2 (en) | 2012-12-17 | 2015-11-17 | Luminescence Technology Corporation | Compound for organic electroluminescence device |
US10103339B2 (en) * | 2015-02-11 | 2018-10-16 | Feng-wen Yen | Iridium complexes and organic electroluminescence device using the same |
US9893305B2 (en) * | 2015-06-01 | 2018-02-13 | Feng-wen Yen | Indenotriphenylene-based iridium complexes for organic electroluminescence device |
US20160380207A1 (en) * | 2015-06-29 | 2016-12-29 | Feng-wen Yen | Triphenylene-based fused biscarbazole derivative and use thereof |
-
2017
- 2017-04-28 US US15/499,938 patent/US10103337B1/en active Active
- 2017-09-29 TW TW106133581A patent/TWI675903B/zh active
- 2017-10-12 CN CN201710949096.XA patent/CN107629068B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW201111469A (en) * | 2009-09-28 | 2011-04-01 | Ritdisplay Corp | Organic electroluminescence device |
US20140166988A1 (en) * | 2012-12-17 | 2014-06-19 | Luminescence Technology Corporation | Organic compound and organic electroluminescent device using the same |
CN105377822A (zh) * | 2013-07-10 | 2016-03-02 | 三星Sdi株式会社 | 有机组合物、有机光电子元件及显示装置 |
JP2016147846A (ja) * | 2015-01-07 | 2016-08-18 | 機光科技股▲分▼有限公司 | 有機エレクトロルミネセント装置用の化合物及びこの化合物を用いる有機エレクトロルミネセント装置 |
Also Published As
Publication number | Publication date |
---|---|
TW201839092A (zh) | 2018-11-01 |
US20180315932A1 (en) | 2018-11-01 |
CN107629068A (zh) | 2018-01-26 |
US10103337B1 (en) | 2018-10-16 |
CN107629068B (zh) | 2021-02-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI675903B (zh) | 有機電致發光材料及其使用 | |
TWI627170B (zh) | 延遲螢光化合物及使用該延遲螢光化合物之有機電致發光裝置 | |
KR102411746B1 (ko) | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
TWI393705B (zh) | Compounds containing m-carbazole phenyl and their use | |
TWI659959B (zh) | 有機電致發光裝置的延遲螢光材料 | |
CN106518603B (zh) | 有机材料及使用其的有机电激发光组件 | |
TWI564272B (zh) | 用於有機電激發光裝置中的化合物及使用該化合物之有機電激發光裝置 | |
TWI614252B (zh) | 化合物及使用其的有機電激發光元件 | |
CN107556319B (zh) | 有机电致发光化合物材料及使用该材料的有机电致发光装置 | |
KR20140141933A (ko) | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
TWI707942B (zh) | 5,12-二氫並四苯衍生物及使用其的有機電激發光元件 | |
US20160380207A1 (en) | Triphenylene-based fused biscarbazole derivative and use thereof | |
CN110964062A (zh) | 铱复合物及使用其的有机电激发光元件 | |
TWI659086B (zh) | 延遲螢光化合物及使用其之有機電致發光元件 | |
TWI651322B (zh) | 延遲螢光化合物及使用其的有機電致發光裝置 | |
TWI637957B (zh) | 有機化合物及使用該有機化合物之有機電致發光裝置 | |
TWI680115B (zh) | 有機材料及使用其的有機電激發光元件 | |
CN105722826A (zh) | 新型有机化合物、包含其的有机电致发光器件及电子设备 | |
KR20160067777A (ko) | 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |