Design Strategy of Decorating Phenylcarbazole with a Donor and Acceptor for Blue‐Shifted Emission in Thermally Activated Delayed Fluorescent Emitters

A series of blue thermally activated delayed fluorescent (TADF) emitters of 1′′‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9,9′′‐diphenyl‐9H,9′′H‐3,3′:9′,4′′‐tercarbazole (TrzCz1) and 3′,6′‐di‐tert‐butyl‐1‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9‐phenyl‐9H‐4,9′‐bicarbazole (TrzCz2) were synthesized through a mole...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemistry : a European journal 2019-09, Vol.25 (50), p.11765-11771
Hauptverfasser: Kim, Do Sik, Lee, Kyung Hyung, Lee, Jun Yeob, Hong, Wan Pyo
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 11771
container_issue 50
container_start_page 11765
container_title Chemistry : a European journal
container_volume 25
creator Kim, Do Sik
Lee, Kyung Hyung
Lee, Jun Yeob
Hong, Wan Pyo
description A series of blue thermally activated delayed fluorescent (TADF) emitters of 1′′‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9,9′′‐diphenyl‐9H,9′′H‐3,3′:9′,4′′‐tercarbazole (TrzCz1) and 3′,6′‐di‐tert‐butyl‐1‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9‐phenyl‐9H‐4,9′‐bicarbazole (TrzCz2) were synthesized through a molecular design approach to decorate phenylcarbazole with a donor and an acceptor. The 1‐ and 4‐positions of the phenylcarbazole core were modified with a diphenyltriazine acceptor and a bicarbazole or tert‐butylcarbazole donor, respectively, through a synthetic strategy to introduce Br at the 1‐position and F at the 4‐position. The TrzCz1 and TrzCz2 emitters showed maximum photoluminescence emission bands at λ=443 and 433 nm, which were blueshifted relative to those of the corresponding TADF emitters with the same donor and acceptor, respectively. In the device application, the TrzCz1 emitter showed a maximum external quantum efficiency of 22.4 %, with a color coordinate of (0.16, 0.21), and the TrzCz2 emitter showed a maximum external quantum efficiency of 9.9 %, with a color coordinate of (0.14, 0.09). This work proved that the design strategy of decorating phenylcarbazole with a donor and an acceptor is effective at blueshifting the emission of TADF emitters. Playing the blues: A phenylcarbazole core was modified with a diphenyltriazine acceptor and a bicarbazole or tert‐butylcarbazole donor to prepare thermally activated delayed fluorescent (TADF) emitters. These new emitters showed maximum photoluminescence emission bands that were blueshifted, relative to those of the corresponding TADF emitters with the same donor and acceptor, and thus, were suitable for application in blue organic light‐emitting diodes.
doi_str_mv 10.1002/chem.201902615
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2254517451</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2254517451</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4105-9e10d4be7fd5f49cbe941e3b6e2dd7fa0f1a4286c89cb2423b90d4860b6cf92e3</originalsourceid><addsrcrecordid>eNqFkc9u1DAQxiMEokvhyhFZ4sIli-04f3wsu1uKVARSyzlynPHGlWMvttMqnHgEbrwfT4KjLUXiwmE0Gs3v-zSjL8teErwmGNO3coBxTTHhmFakfJStSElJXtRV-ThbYc7qvCoLfpI9C-EGY8yronianRSENlXZkFX2cwtB7y26il5E2M_IKbQF6dKk7R59HsDORgrfiW_OALrTcUACbZ11HgnbozMp4RDToFK9MxP8-v7jatAqQo92ow5BO4u0RdcD-FEYMydF1Ldi2W_BiDn1czM5D0GCjYsmRvDhefZECRPgxX0_zb6c7643F_nlp_cfNmeXuWQElzkHgnvWQa36UjEuO-CMQNFVQPu-VgIrIlj6VTZpRxktOp74psJdJRWnUJxmb46-B---ThBim46WYIyw4KbQUlqyktSpEvr6H_TGTd6m6xLVMM5oxRZqfaSkdyF4UO3B61H4uSW4XSJrl8jah8iS4NW97dSN0D_gfzJKAD8Cd9rA_B-7dnOx-_jX_DceeKYO</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2284942641</pqid></control><display><type>article</type><title>Design Strategy of Decorating Phenylcarbazole with a Donor and Acceptor for Blue‐Shifted Emission in Thermally Activated Delayed Fluorescent Emitters</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Kim, Do Sik ; Lee, Kyung Hyung ; Lee, Jun Yeob ; Hong, Wan Pyo</creator><creatorcontrib>Kim, Do Sik ; Lee, Kyung Hyung ; Lee, Jun Yeob ; Hong, Wan Pyo</creatorcontrib><description>A series of blue thermally activated delayed fluorescent (TADF) emitters of 1′′‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9,9′′‐diphenyl‐9H,9′′H‐3,3′:9′,4′′‐tercarbazole (TrzCz1) and 3′,6′‐di‐tert‐butyl‐1‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9‐phenyl‐9H‐4,9′‐bicarbazole (TrzCz2) were synthesized through a molecular design approach to decorate phenylcarbazole with a donor and an acceptor. The 1‐ and 4‐positions of the phenylcarbazole core were modified with a diphenyltriazine acceptor and a bicarbazole or tert‐butylcarbazole donor, respectively, through a synthetic strategy to introduce Br at the 1‐position and F at the 4‐position. The TrzCz1 and TrzCz2 emitters showed maximum photoluminescence emission bands at λ=443 and 433 nm, which were blueshifted relative to those of the corresponding TADF emitters with the same donor and acceptor, respectively. In the device application, the TrzCz1 emitter showed a maximum external quantum efficiency of 22.4 %, with a color coordinate of (0.16, 0.21), and the TrzCz2 emitter showed a maximum external quantum efficiency of 9.9 %, with a color coordinate of (0.14, 0.09). This work proved that the design strategy of decorating phenylcarbazole with a donor and an acceptor is effective at blueshifting the emission of TADF emitters. Playing the blues: A phenylcarbazole core was modified with a diphenyltriazine acceptor and a bicarbazole or tert‐butylcarbazole donor to prepare thermally activated delayed fluorescent (TADF) emitters. These new emitters showed maximum photoluminescence emission bands that were blueshifted, relative to those of the corresponding TADF emitters with the same donor and acceptor, and thus, were suitable for application in blue organic light‐emitting diodes.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201902615</identifier><identifier>PMID: 31286581</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Chemical synthesis ; Chemistry ; Color ; Decoration ; Design ; donor–acceptor systems ; electrochemistry ; Emission ; Emissions ; Emitters ; Fluorescence ; organic light-emitting diodes ; Photoluminescence ; Photons ; Quantum efficiency ; Strategy ; substituent effects</subject><ispartof>Chemistry : a European journal, 2019-09, Vol.25 (50), p.11765-11771</ispartof><rights>2019 Wiley‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4105-9e10d4be7fd5f49cbe941e3b6e2dd7fa0f1a4286c89cb2423b90d4860b6cf92e3</citedby><cites>FETCH-LOGICAL-c4105-9e10d4be7fd5f49cbe941e3b6e2dd7fa0f1a4286c89cb2423b90d4860b6cf92e3</cites><orcidid>0000-0002-7677-0605</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201902615$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201902615$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31286581$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Do Sik</creatorcontrib><creatorcontrib>Lee, Kyung Hyung</creatorcontrib><creatorcontrib>Lee, Jun Yeob</creatorcontrib><creatorcontrib>Hong, Wan Pyo</creatorcontrib><title>Design Strategy of Decorating Phenylcarbazole with a Donor and Acceptor for Blue‐Shifted Emission in Thermally Activated Delayed Fluorescent Emitters</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>A series of blue thermally activated delayed fluorescent (TADF) emitters of 1′′‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9,9′′‐diphenyl‐9H,9′′H‐3,3′:9′,4′′‐tercarbazole (TrzCz1) and 3′,6′‐di‐tert‐butyl‐1‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9‐phenyl‐9H‐4,9′‐bicarbazole (TrzCz2) were synthesized through a molecular design approach to decorate phenylcarbazole with a donor and an acceptor. The 1‐ and 4‐positions of the phenylcarbazole core were modified with a diphenyltriazine acceptor and a bicarbazole or tert‐butylcarbazole donor, respectively, through a synthetic strategy to introduce Br at the 1‐position and F at the 4‐position. The TrzCz1 and TrzCz2 emitters showed maximum photoluminescence emission bands at λ=443 and 433 nm, which were blueshifted relative to those of the corresponding TADF emitters with the same donor and acceptor, respectively. In the device application, the TrzCz1 emitter showed a maximum external quantum efficiency of 22.4 %, with a color coordinate of (0.16, 0.21), and the TrzCz2 emitter showed a maximum external quantum efficiency of 9.9 %, with a color coordinate of (0.14, 0.09). This work proved that the design strategy of decorating phenylcarbazole with a donor and an acceptor is effective at blueshifting the emission of TADF emitters. Playing the blues: A phenylcarbazole core was modified with a diphenyltriazine acceptor and a bicarbazole or tert‐butylcarbazole donor to prepare thermally activated delayed fluorescent (TADF) emitters. These new emitters showed maximum photoluminescence emission bands that were blueshifted, relative to those of the corresponding TADF emitters with the same donor and acceptor, and thus, were suitable for application in blue organic light‐emitting diodes.</description><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Color</subject><subject>Decoration</subject><subject>Design</subject><subject>donor–acceptor systems</subject><subject>electrochemistry</subject><subject>Emission</subject><subject>Emissions</subject><subject>Emitters</subject><subject>Fluorescence</subject><subject>organic light-emitting diodes</subject><subject>Photoluminescence</subject><subject>Photons</subject><subject>Quantum efficiency</subject><subject>Strategy</subject><subject>substituent effects</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkc9u1DAQxiMEokvhyhFZ4sIli-04f3wsu1uKVARSyzlynPHGlWMvttMqnHgEbrwfT4KjLUXiwmE0Gs3v-zSjL8teErwmGNO3coBxTTHhmFakfJStSElJXtRV-ThbYc7qvCoLfpI9C-EGY8yronianRSENlXZkFX2cwtB7y26il5E2M_IKbQF6dKk7R59HsDORgrfiW_OALrTcUACbZ11HgnbozMp4RDToFK9MxP8-v7jatAqQo92ow5BO4u0RdcD-FEYMydF1Ldi2W_BiDn1czM5D0GCjYsmRvDhefZECRPgxX0_zb6c7643F_nlp_cfNmeXuWQElzkHgnvWQa36UjEuO-CMQNFVQPu-VgIrIlj6VTZpRxktOp74psJdJRWnUJxmb46-B---ThBim46WYIyw4KbQUlqyktSpEvr6H_TGTd6m6xLVMM5oxRZqfaSkdyF4UO3B61H4uSW4XSJrl8jah8iS4NW97dSN0D_gfzJKAD8Cd9rA_B-7dnOx-_jX_DceeKYO</recordid><startdate>20190906</startdate><enddate>20190906</enddate><creator>Kim, Do Sik</creator><creator>Lee, Kyung Hyung</creator><creator>Lee, Jun Yeob</creator><creator>Hong, Wan Pyo</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7677-0605</orcidid></search><sort><creationdate>20190906</creationdate><title>Design Strategy of Decorating Phenylcarbazole with a Donor and Acceptor for Blue‐Shifted Emission in Thermally Activated Delayed Fluorescent Emitters</title><author>Kim, Do Sik ; Lee, Kyung Hyung ; Lee, Jun Yeob ; Hong, Wan Pyo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4105-9e10d4be7fd5f49cbe941e3b6e2dd7fa0f1a4286c89cb2423b90d4860b6cf92e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Color</topic><topic>Decoration</topic><topic>Design</topic><topic>donor–acceptor systems</topic><topic>electrochemistry</topic><topic>Emission</topic><topic>Emissions</topic><topic>Emitters</topic><topic>Fluorescence</topic><topic>organic light-emitting diodes</topic><topic>Photoluminescence</topic><topic>Photons</topic><topic>Quantum efficiency</topic><topic>Strategy</topic><topic>substituent effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Do Sik</creatorcontrib><creatorcontrib>Lee, Kyung Hyung</creatorcontrib><creatorcontrib>Lee, Jun Yeob</creatorcontrib><creatorcontrib>Hong, Wan Pyo</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Do Sik</au><au>Lee, Kyung Hyung</au><au>Lee, Jun Yeob</au><au>Hong, Wan Pyo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design Strategy of Decorating Phenylcarbazole with a Donor and Acceptor for Blue‐Shifted Emission in Thermally Activated Delayed Fluorescent Emitters</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2019-09-06</date><risdate>2019</risdate><volume>25</volume><issue>50</issue><spage>11765</spage><epage>11771</epage><pages>11765-11771</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A series of blue thermally activated delayed fluorescent (TADF) emitters of 1′′‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9,9′′‐diphenyl‐9H,9′′H‐3,3′:9′,4′′‐tercarbazole (TrzCz1) and 3′,6′‐di‐tert‐butyl‐1‐(4,6‐diphenyl‐1,3,5‐triazin‐2‐yl)‐9‐phenyl‐9H‐4,9′‐bicarbazole (TrzCz2) were synthesized through a molecular design approach to decorate phenylcarbazole with a donor and an acceptor. The 1‐ and 4‐positions of the phenylcarbazole core were modified with a diphenyltriazine acceptor and a bicarbazole or tert‐butylcarbazole donor, respectively, through a synthetic strategy to introduce Br at the 1‐position and F at the 4‐position. The TrzCz1 and TrzCz2 emitters showed maximum photoluminescence emission bands at λ=443 and 433 nm, which were blueshifted relative to those of the corresponding TADF emitters with the same donor and acceptor, respectively. In the device application, the TrzCz1 emitter showed a maximum external quantum efficiency of 22.4 %, with a color coordinate of (0.16, 0.21), and the TrzCz2 emitter showed a maximum external quantum efficiency of 9.9 %, with a color coordinate of (0.14, 0.09). This work proved that the design strategy of decorating phenylcarbazole with a donor and an acceptor is effective at blueshifting the emission of TADF emitters. Playing the blues: A phenylcarbazole core was modified with a diphenyltriazine acceptor and a bicarbazole or tert‐butylcarbazole donor to prepare thermally activated delayed fluorescent (TADF) emitters. These new emitters showed maximum photoluminescence emission bands that were blueshifted, relative to those of the corresponding TADF emitters with the same donor and acceptor, and thus, were suitable for application in blue organic light‐emitting diodes.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31286581</pmid><doi>10.1002/chem.201902615</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-7677-0605</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0947-6539
ispartof Chemistry : a European journal, 2019-09, Vol.25 (50), p.11765-11771
issn 0947-6539
1521-3765
language eng
recordid cdi_proquest_miscellaneous_2254517451
source Wiley Online Library Journals Frontfile Complete
subjects Chemical synthesis
Chemistry
Color
Decoration
Design
donor–acceptor systems
electrochemistry
Emission
Emissions
Emitters
Fluorescence
organic light-emitting diodes
Photoluminescence
Photons
Quantum efficiency
Strategy
substituent effects
title Design Strategy of Decorating Phenylcarbazole with a Donor and Acceptor for Blue‐Shifted Emission in Thermally Activated Delayed Fluorescent Emitters
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-20T01%3A21%3A59IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Design%20Strategy%20of%20Decorating%20Phenylcarbazole%20with%20a%20Donor%20and%20Acceptor%20for%20Blue%E2%80%90Shifted%20Emission%20in%20Thermally%20Activated%20Delayed%20Fluorescent%20Emitters&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Kim,%20Do%20Sik&rft.date=2019-09-06&rft.volume=25&rft.issue=50&rft.spage=11765&rft.epage=11771&rft.pages=11765-11771&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.201902615&rft_dat=%3Cproquest_cross%3E2254517451%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2284942641&rft_id=info:pmid/31286581&rfr_iscdi=true