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...
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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 |
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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 & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & 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 & 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> |
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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 |
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