WO2020211128A1 - Matériau à fluorescence retardée activé thermiquement, procédé de préparation correspondant et dispositif à diode électroluminescente organique - Google Patents
Matériau à fluorescence retardée activé thermiquement, procédé de préparation correspondant et dispositif à diode électroluminescente organique Download PDFInfo
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- WO2020211128A1 WO2020211128A1 PCT/CN2019/085649 CN2019085649W WO2020211128A1 WO 2020211128 A1 WO2020211128 A1 WO 2020211128A1 CN 2019085649 W CN2019085649 W CN 2019085649W WO 2020211128 A1 WO2020211128 A1 WO 2020211128A1
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- thermally activated
- activated delayed
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- 0 C(CC=C1)C2C1=C1OC3C(C=C*C4)=C4C=CC3NC1=CC2 Chemical compound C(CC=C1)C2C1=C1OC3C(C=C*C4)=C4C=CC3NC1=CC2 0.000 description 6
- BQSGGZBOTBRTDX-UHFFFAOYSA-N C(C12)=CC=CC1Nc1ccccc1C21c2ccccc2-c2c1cccc2 Chemical compound C(C12)=CC=CC1Nc1ccccc1C21c2ccccc2-c2c1cccc2 BQSGGZBOTBRTDX-UHFFFAOYSA-N 0.000 description 2
- CFPWELBPYIDZDM-UHFFFAOYSA-N C1C=C2NC3C=CC=CC3OC2=CC1 Chemical compound C1C=C2NC3C=CC=CC3OC2=CC1 CFPWELBPYIDZDM-UHFFFAOYSA-N 0.000 description 2
- YLBUZDUBUCGFPA-UHFFFAOYSA-N CC1(C)C2=CCCC=C2NC2C=CC=CC12 Chemical compound CC1(C)C2=CCCC=C2NC2C=CC=CC12 YLBUZDUBUCGFPA-UHFFFAOYSA-N 0.000 description 2
- IIPRZFWOSCKSIM-UHFFFAOYSA-N CC1(C)c2cc(C)ccc2Nc2c1cc(C)cc2 Chemical compound CC1(C)c2cc(C)ccc2Nc2c1cc(C)cc2 IIPRZFWOSCKSIM-UHFFFAOYSA-N 0.000 description 2
- HWTHOPMRUCFPBX-UHFFFAOYSA-N c1ccc(C2(c3ccccc3)c3ccccc3Nc3c2cccc3)cc1 Chemical compound c1ccc(C2(c3ccccc3)c3ccccc3Nc3c2cccc3)cc1 HWTHOPMRUCFPBX-UHFFFAOYSA-N 0.000 description 2
- XDWDZKGXZKYUCL-UHFFFAOYSA-N C(C12)C=CC=C1Nc1c2cccc1 Chemical compound C(C12)C=CC=C1Nc1c2cccc1 XDWDZKGXZKYUCL-UHFFFAOYSA-N 0.000 description 1
- UMAAQFKOTADJQZ-UHFFFAOYSA-N C1C=C(c2ccccc2[SiH-]23c(cccc4)c4NC4C=CC=CC24)C3=CC1 Chemical compound C1C=C(c2ccccc2[SiH-]23c(cccc4)c4NC4C=CC=CC24)C3=CC1 UMAAQFKOTADJQZ-UHFFFAOYSA-N 0.000 description 1
- HBBCRBJQHYMKCM-UHFFFAOYSA-N C1C=C2NC3C=CC=CC3SC2=CC1 Chemical compound C1C=C2NC3C=CC=CC3SC2=CC1 HBBCRBJQHYMKCM-UHFFFAOYSA-N 0.000 description 1
- ILXXOAPNOVRUFN-UHFFFAOYSA-N C1C=C2Nc(cccc3)c3SC2=CC1 Chemical compound C1C=C2Nc(cccc3)c3SC2=CC1 ILXXOAPNOVRUFN-UHFFFAOYSA-N 0.000 description 1
- FILCCEBCZHMKQM-UHFFFAOYSA-N CC(C)(C(C(C=C1)NC2=CC3)C=C1N(c1ccccc1)C1=CCCC=C1)C2=CC3N(C1C=CC=CC1)c1ccccc1 Chemical compound CC(C)(C(C(C=C1)NC2=CC3)C=C1N(c1ccccc1)C1=CCCC=C1)C2=CC3N(C1C=CC=CC1)c1ccccc1 FILCCEBCZHMKQM-UHFFFAOYSA-N 0.000 description 1
- KSBXBCSZRFLMGW-UHFFFAOYSA-N CC(C)(C(C(C=C1)NC2=CC3)C=C1N(c1ccccc1)c1ccccc1)C2=CC3N(C1C=CC=CC1)c1ccccc1 Chemical compound CC(C)(C(C(C=C1)NC2=CC3)C=C1N(c1ccccc1)c1ccccc1)C2=CC3N(C1C=CC=CC1)c1ccccc1 KSBXBCSZRFLMGW-UHFFFAOYSA-N 0.000 description 1
- BSYSVMAYIVGGEN-UHFFFAOYSA-N CC(C)(C(C(C=C1)NC2=CC3)C=C1[n]1c4ccccc4c4c1cccc4)C2=CC3[n]1c2ccccc2c2ccccc12 Chemical compound CC(C)(C(C(C=C1)NC2=CC3)C=C1[n]1c4ccccc4c4c1cccc4)C2=CC3[n]1c2ccccc2c2ccccc12 BSYSVMAYIVGGEN-UHFFFAOYSA-N 0.000 description 1
- JYZNATGUYXNRCR-UHFFFAOYSA-N CC(C)(C1C2=CC=CC1)c(cccc1)c1N2C1=CC2C(C)(C)c(cc(cc3)N4c5ccccc5C(C)(C)c5ccccc45)c3NC2C=C1 Chemical compound CC(C)(C1C2=CC=CC1)c(cccc1)c1N2C1=CC2C(C)(C)c(cc(cc3)N4c5ccccc5C(C)(C)c5ccccc45)c3NC2C=C1 JYZNATGUYXNRCR-UHFFFAOYSA-N 0.000 description 1
- HFVKNYYTBSAMGP-UHFFFAOYSA-N CC(C)(c(cc(cc1)N2C(C=CCC3)=C3Oc3ccccc23)c1NC1=CC2)C1=CC2N1C(CCC=C2)=C2OC2=CC=CCC12 Chemical compound CC(C)(c(cc(cc1)N2C(C=CCC3)=C3Oc3ccccc23)c1NC1=CC2)C1=CC2N1C(CCC=C2)=C2OC2=CC=CCC12 HFVKNYYTBSAMGP-UHFFFAOYSA-N 0.000 description 1
- AUWLSXVKDXAKHQ-UHFFFAOYSA-N CC(C)(c(cc(cc1)N2c(cccc3)c3Oc3c2cccc3)c1NC1=CC2)C1=CC2N1C(CCC=C2)=C2OC2=CC=CCC12 Chemical compound CC(C)(c(cc(cc1)N2c(cccc3)c3Oc3c2cccc3)c1NC1=CC2)C1=CC2N1C(CCC=C2)=C2OC2=CC=CCC12 AUWLSXVKDXAKHQ-UHFFFAOYSA-N 0.000 description 1
- RLJLEDKMKCLDKF-UHFFFAOYSA-N CC1(C)c(cc(cc2)-[n]3c4ccccc4c4c3cccc4)c2NC2C=CC([n]3c4ccccc4c4c3cccc4)=CC12 Chemical compound CC1(C)c(cc(cc2)-[n]3c4ccccc4c4c3cccc4)c2NC2C=CC([n]3c4ccccc4c4c3cccc4)=CC12 RLJLEDKMKCLDKF-UHFFFAOYSA-N 0.000 description 1
- FAHOMWHBJZNSNP-UHFFFAOYSA-N CCCCC1(CCCC)C2=CCCC=C2Nc2c1cccc2 Chemical compound CCCCC1(CCCC)C2=CCCC=C2Nc2c1cccc2 FAHOMWHBJZNSNP-UHFFFAOYSA-N 0.000 description 1
- OFHBBDRLHHETNR-UHFFFAOYSA-N CCCCC1(CCCC)c2ccccc2Nc2c1cccc2 Chemical compound CCCCC1(CCCC)c2ccccc2Nc2c1cccc2 OFHBBDRLHHETNR-UHFFFAOYSA-N 0.000 description 1
- ISXRNNSNJXYWKP-UHFFFAOYSA-N N#CC(C1C#N)C(c2ccccc2)=C2N=C(c3nccnc3-c3c4nccn3)C4=NC2=C1I Chemical compound N#CC(C1C#N)C(c2ccccc2)=C2N=C(c3nccnc3-c3c4nccn3)C4=NC2=C1I ISXRNNSNJXYWKP-UHFFFAOYSA-N 0.000 description 1
- MRMVIQLNZQIXDM-UHFFFAOYSA-N N#Cc(c(C#N)c1Br)c(-c2ccccc2)c2c1nc(c1c(c3nccnc33)nccn1)c3n2 Chemical compound N#Cc(c(C#N)c1Br)c(-c2ccccc2)c2c1nc(c1c(c3nccnc33)nccn1)c3n2 MRMVIQLNZQIXDM-UHFFFAOYSA-N 0.000 description 1
- PXOMBIXNWVOMSE-UHFFFAOYSA-N N#Cc(c(C#N)c1N2c3ccccc3Sc3c2cccc3)c(-c2ccccc2)c2c1NC(c1nccnc1-c1c3nccn1)C3=N2 Chemical compound N#Cc(c(C#N)c1N2c3ccccc3Sc3c2cccc3)c(-c2ccccc2)c2c1NC(c1nccnc1-c1c3nccn1)C3=N2 PXOMBIXNWVOMSE-UHFFFAOYSA-N 0.000 description 1
- WSJGJLBAFKAYNP-UHFFFAOYSA-N N#Cc1c(-c2ccccc2)c2nc(c3c(c4c5[nH]cn4)nc[nH]3)c5nc2c(N2c3ccccc3OC3C=CC=CC23)c1C#N Chemical compound N#Cc1c(-c2ccccc2)c2nc(c3c(c4c5[nH]cn4)nc[nH]3)c5nc2c(N2c3ccccc3OC3C=CC=CC23)c1C#N WSJGJLBAFKAYNP-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N c(cc1)cc2c1Sc1ccccc1N2 Chemical compound c(cc1)cc2c1Sc1ccccc1N2 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N c(cc1)cc2c1[nH]c1c2cccc1 Chemical compound c(cc1)cc2c1[nH]c1c2cccc1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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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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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- 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
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- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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- Engineering & Computer Science (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
La présente invention concerne un matériau à fluorescence retardée activé thermiquement, un procédé de préparation correspondant et un dispositif à diode électroluminescente organique. La structure de formule générale du matériau à fluorescence retardée activé thermiquement est représentée dans la formule suivante I : (I), Dans laquelle R1 représente un groupe chimique d'un donneur d'électrons, et R2 représente un groupe chimique agissant en tant qu'accepteur d'électrons. Le matériau à fluorescence retardée activé thermiquement selon la présente invention a un taux de croisement intersystème inverse ultra-élevé et une efficacité d'émission de lumière élevée, et est un matériau TADF à lumière rouge ayant des caractéristiques TADF significatives. Le matériau à fluorescence retardée activé thermiquement peut être utilisé comme matériau de base d'une couche électroluminescente dans un dispositif à diode électroluminescente organique, ce qui permet d'améliorer de manière efficace l'efficacité luminescente du dispositif à diode électroluminescente organique, et le dispositif à diode électroluminescente organique basé sur le matériau à fluorescence retardée activé thermiquement selon la présente invention présente une efficacité de dispositif très élevée.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CN201910305506.6A CN110003223A (zh) | 2019-04-16 | 2019-04-16 | 热活化延迟荧光材料及其制备方法与有机电致发光二极管器件 |
CN201910305506.6 | 2019-04-16 |
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WO2020211128A1 true WO2020211128A1 (fr) | 2020-10-22 |
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PCT/CN2019/085649 WO2020211128A1 (fr) | 2019-04-16 | 2019-05-06 | Matériau à fluorescence retardée activé thermiquement, procédé de préparation correspondant et dispositif à diode électroluminescente organique |
Country Status (2)
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CN (1) | CN110003223A (fr) |
WO (1) | WO2020211128A1 (fr) |
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CN113527279A (zh) * | 2021-07-13 | 2021-10-22 | 京东方科技集团股份有限公司 | 一种发光薄膜及其制备方法、发光器件及显示装置 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010027885A (ja) * | 2008-07-22 | 2010-02-04 | Sony Corp | 有機電界発光素子 |
WO2013031794A1 (fr) * | 2011-09-02 | 2013-03-07 | コニカミノルタホールディングス株式会社 | Élément électroluminescent organique, dispositif d'affichage, et dispositif d'éclairage |
-
2019
- 2019-04-16 CN CN201910305506.6A patent/CN110003223A/zh not_active Withdrawn
- 2019-05-06 WO PCT/CN2019/085649 patent/WO2020211128A1/fr active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010027885A (ja) * | 2008-07-22 | 2010-02-04 | Sony Corp | 有機電界発光素子 |
WO2013031794A1 (fr) * | 2011-09-02 | 2013-03-07 | コニカミノルタホールディングス株式会社 | Élément électroluminescent organique, dispositif d'affichage, et dispositif d'éclairage |
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