Synthesis and characterization of greenish-blue emitting vinyl copolymer containing pyrene and triarylamine moieties

High yield, high Tg, soluble and greenish‐blue emitting vinyl copolymer. Two fluorescent monomers N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine (vinyl‐PyPA) and 1‐vinyl pyrene (VPy) were synthesized in good yields. A series of soluble conductive vinyl copolymers P(PyPA‐co‐VPy) containing vinyl‐PyPA and VP...

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Veröffentlicht in:Polymer international 2014-10, Vol.63 (10), p.1797-1805
Hauptverfasser: Wang, Jianli, Leung, Louis M, SO, Shu-Kong, Chan, Cyrus Y H, Wong, Michael Y
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container_end_page 1805
container_issue 10
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container_title Polymer international
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creator Wang, Jianli
Leung, Louis M
SO, Shu-Kong
Chan, Cyrus Y H
Wong, Michael Y
description High yield, high Tg, soluble and greenish‐blue emitting vinyl copolymer. Two fluorescent monomers N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine (vinyl‐PyPA) and 1‐vinyl pyrene (VPy) were synthesized in good yields. A series of soluble conductive vinyl copolymers P(PyPA‐co‐VPy) containing vinyl‐PyPA and VPy moieties in different composition ratios were prepared by free radical solution polymerization. These copolymers showed high Tg (190−201 °C) and good thermal stability. The photoluminescence emission maxima of the copolymers were all in the range 474.5−478.5 nm, which was similar to the poly(N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine) (P(PyPA)) (475 nm) but blue shifted compared with poly(1‐vinyl pyrene) (PVPy) (490.5 nm). The lifetime of the copolymers increased from 10.2 to 29.7 ns with an increase in pyrene content. The copolymers had higher quantum yields (0.51) than those of the homopolymers of P(PyPA) (0.48) and PVPy (0.13). The highest occupied molecular orbital of the copolymers remained relatively unchanged from P(PyPA), while the lowest unoccupied molecular orbital varied from −2.41 eV to −2.51 eV with an increase in pyrene ratio in the copolymers. The energy bandgaps of the copolymers (from 2.70 eV to 2.81 eV) were smaller than those of P(PyPA) (2.82 eV) and PVPy (3.47 eV). Two polymer light‐emitting diode (PLED) series were attempted including indium tin oxide (ITO) (fluorocarbon (CFx) treated)/P(PyPA‐co‐VPy)/LiF/Al and ITO(CFx treated)/P(PyPA‐co‐VPy)/1,3,5‐Tri(1‐phenyl‐1H‐benzo[d]imidazol‐2‐yl)phenyl (TPBi)/LiF/Al. The results suggested that the PyPA moiety is hole conducting and the PLEDs can achieve high luminance from 650 to 1150 cd m−2 (at 100 mA cm−2) only when an electron injecting layer TPBi is employed. © 2013 Society of Chemical Industry
doi_str_mv 10.1002/pi.4682
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Two fluorescent monomers N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine (vinyl‐PyPA) and 1‐vinyl pyrene (VPy) were synthesized in good yields. A series of soluble conductive vinyl copolymers P(PyPA‐co‐VPy) containing vinyl‐PyPA and VPy moieties in different composition ratios were prepared by free radical solution polymerization. These copolymers showed high Tg (190−201 °C) and good thermal stability. The photoluminescence emission maxima of the copolymers were all in the range 474.5−478.5 nm, which was similar to the poly(N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine) (P(PyPA)) (475 nm) but blue shifted compared with poly(1‐vinyl pyrene) (PVPy) (490.5 nm). The lifetime of the copolymers increased from 10.2 to 29.7 ns with an increase in pyrene content. The copolymers had higher quantum yields (0.51) than those of the homopolymers of P(PyPA) (0.48) and PVPy (0.13). The highest occupied molecular orbital of the copolymers remained relatively unchanged from P(PyPA), while the lowest unoccupied molecular orbital varied from −2.41 eV to −2.51 eV with an increase in pyrene ratio in the copolymers. The energy bandgaps of the copolymers (from 2.70 eV to 2.81 eV) were smaller than those of P(PyPA) (2.82 eV) and PVPy (3.47 eV). Two polymer light‐emitting diode (PLED) series were attempted including indium tin oxide (ITO) (fluorocarbon (CFx) treated)/P(PyPA‐co‐VPy)/LiF/Al and ITO(CFx treated)/P(PyPA‐co‐VPy)/1,3,5‐Tri(1‐phenyl‐1H‐benzo[d]imidazol‐2‐yl)phenyl (TPBi)/LiF/Al. The results suggested that the PyPA moiety is hole conducting and the PLEDs can achieve high luminance from 650 to 1150 cd m−2 (at 100 mA cm−2) only when an electron injecting layer TPBi is employed. © 2013 Society of Chemical Industry</description><identifier>ISSN: 0959-8103</identifier><identifier>EISSN: 1097-0126</identifier><identifier>DOI: 10.1002/pi.4682</identifier><identifier>CODEN: PLYIEI</identifier><language>eng</language><publisher>Chichester, UK: John Wiley &amp; Sons, Ltd</publisher><subject>Aluminum ; Applied sciences ; Copolymers ; Electronics ; Emittance ; Exact sciences and technology ; free radical solution polymerization ; Indium tin oxide ; Luminance ; Molecular orbitals ; Optoelectronic devices ; Organic polymers ; Physicochemistry of polymers ; poly(1-vinyl pyrene) ; poly(N-phenyl-N-(4-vinylphenyl)pyren-1-amine) ; Polymers with particular properties ; Preparation, kinetics, thermodynamics, mechanism and catalysts ; Pyrenes ; Semiconductor electronics. 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Solid state devices ; vinyl copolymer ; Vinyl copolymers</subject><ispartof>Polymer international, 2014-10, Vol.63 (10), p.1797-1805</ispartof><rights>2013 Society of Chemical Industry</rights><rights>2015 INIST-CNRS</rights><rights>2014 Society of Chemical Industry</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5632-7ce0fd352e2987604b97e269624aa2e282a6e7f75ddb7fd9b5dabb2baafb6b623</citedby><cites>FETCH-LOGICAL-c5632-7ce0fd352e2987604b97e269624aa2e282a6e7f75ddb7fd9b5dabb2baafb6b623</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpi.4682$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpi.4682$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=28752674$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Jianli</creatorcontrib><creatorcontrib>Leung, Louis M</creatorcontrib><creatorcontrib>SO, Shu-Kong</creatorcontrib><creatorcontrib>Chan, Cyrus Y H</creatorcontrib><creatorcontrib>Wong, Michael Y</creatorcontrib><title>Synthesis and characterization of greenish-blue emitting vinyl copolymer containing pyrene and triarylamine moieties</title><title>Polymer international</title><addtitle>Polym. Int</addtitle><description>High yield, high Tg, soluble and greenish‐blue emitting vinyl copolymer. Two fluorescent monomers N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine (vinyl‐PyPA) and 1‐vinyl pyrene (VPy) were synthesized in good yields. A series of soluble conductive vinyl copolymers P(PyPA‐co‐VPy) containing vinyl‐PyPA and VPy moieties in different composition ratios were prepared by free radical solution polymerization. These copolymers showed high Tg (190−201 °C) and good thermal stability. The photoluminescence emission maxima of the copolymers were all in the range 474.5−478.5 nm, which was similar to the poly(N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine) (P(PyPA)) (475 nm) but blue shifted compared with poly(1‐vinyl pyrene) (PVPy) (490.5 nm). The lifetime of the copolymers increased from 10.2 to 29.7 ns with an increase in pyrene content. The copolymers had higher quantum yields (0.51) than those of the homopolymers of P(PyPA) (0.48) and PVPy (0.13). The highest occupied molecular orbital of the copolymers remained relatively unchanged from P(PyPA), while the lowest unoccupied molecular orbital varied from −2.41 eV to −2.51 eV with an increase in pyrene ratio in the copolymers. The energy bandgaps of the copolymers (from 2.70 eV to 2.81 eV) were smaller than those of P(PyPA) (2.82 eV) and PVPy (3.47 eV). Two polymer light‐emitting diode (PLED) series were attempted including indium tin oxide (ITO) (fluorocarbon (CFx) treated)/P(PyPA‐co‐VPy)/LiF/Al and ITO(CFx treated)/P(PyPA‐co‐VPy)/1,3,5‐Tri(1‐phenyl‐1H‐benzo[d]imidazol‐2‐yl)phenyl (TPBi)/LiF/Al. The results suggested that the PyPA moiety is hole conducting and the PLEDs can achieve high luminance from 650 to 1150 cd m−2 (at 100 mA cm−2) only when an electron injecting layer TPBi is employed. © 2013 Society of Chemical Industry</description><subject>Aluminum</subject><subject>Applied sciences</subject><subject>Copolymers</subject><subject>Electronics</subject><subject>Emittance</subject><subject>Exact sciences and technology</subject><subject>free radical solution polymerization</subject><subject>Indium tin oxide</subject><subject>Luminance</subject><subject>Molecular orbitals</subject><subject>Optoelectronic devices</subject><subject>Organic polymers</subject><subject>Physicochemistry of polymers</subject><subject>poly(1-vinyl pyrene)</subject><subject>poly(N-phenyl-N-(4-vinylphenyl)pyren-1-amine)</subject><subject>Polymers with particular properties</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>Pyrenes</subject><subject>Semiconductor electronics. Microelectronics. Optoelectronics. Solid state devices</subject><subject>vinyl copolymer</subject><subject>Vinyl copolymers</subject><issn>0959-8103</issn><issn>1097-0126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp10N-L1DAQB_AgCq6n-C8URBSkZ5JukubRW_Q8OE7Bn29hmk5v52zTmmTV-tfbdZd7EHyaMPnwZWYYeyz4qeBcvpzodK1reYetBLem5ELqu2zFrbJlLXh1nz1I6YZzXltrVyx_mEPeYqJUQGgLv4UIPmOk35BpDMXYFdcRMVDalk2_wwIHypnCdfGDwtwXfpzGfh4wLq-QgcL-a5ojBvwbmCNBnHsYaGkMI2EmTA_ZvQ76hI-O9YR9evP64-Ztefnu_GLz6rL0SleyNB5511ZKorS10XzdWINSWy3XAEuzlqDRdEa1bWO61jaqhaaRDUDX6EbL6oQ9P-ROcfy-w5TdQMlj30PAcZec0JILUQlpFvrkH3oz7mJYpnNCKasqIbRe1LOD8nFMKWLnpkjDsqAT3O2v7yZy--sv8ukxD5KHvosQPKVbLmujpDbrxb04uJ_U4_y_OPf-4phaHjSljL9uNcRvTpvKKPfl6tzJK1V_5psz97X6A7pjo44</recordid><startdate>201410</startdate><enddate>201410</enddate><creator>Wang, Jianli</creator><creator>Leung, Louis M</creator><creator>SO, Shu-Kong</creator><creator>Chan, Cyrus Y H</creator><creator>Wong, Michael Y</creator><general>John Wiley &amp; Sons, Ltd</general><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>F28</scope><scope>FR3</scope><scope>JG9</scope><scope>7SP</scope><scope>L7M</scope></search><sort><creationdate>201410</creationdate><title>Synthesis and characterization of greenish-blue emitting vinyl copolymer containing pyrene and triarylamine moieties</title><author>Wang, Jianli ; Leung, Louis M ; SO, Shu-Kong ; Chan, Cyrus Y H ; Wong, Michael Y</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5632-7ce0fd352e2987604b97e269624aa2e282a6e7f75ddb7fd9b5dabb2baafb6b623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Aluminum</topic><topic>Applied sciences</topic><topic>Copolymers</topic><topic>Electronics</topic><topic>Emittance</topic><topic>Exact sciences and technology</topic><topic>free radical solution polymerization</topic><topic>Indium tin oxide</topic><topic>Luminance</topic><topic>Molecular orbitals</topic><topic>Optoelectronic devices</topic><topic>Organic polymers</topic><topic>Physicochemistry of polymers</topic><topic>poly(1-vinyl pyrene)</topic><topic>poly(N-phenyl-N-(4-vinylphenyl)pyren-1-amine)</topic><topic>Polymers with particular properties</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>Pyrenes</topic><topic>Semiconductor electronics. Microelectronics. Optoelectronics. Solid state devices</topic><topic>vinyl copolymer</topic><topic>Vinyl copolymers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Jianli</creatorcontrib><creatorcontrib>Leung, Louis M</creatorcontrib><creatorcontrib>SO, Shu-Kong</creatorcontrib><creatorcontrib>Chan, Cyrus Y H</creatorcontrib><creatorcontrib>Wong, Michael Y</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>ANTE: Abstracts in New Technology &amp; Engineering</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Electronics &amp; Communications Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Polymer international</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Jianli</au><au>Leung, Louis M</au><au>SO, Shu-Kong</au><au>Chan, Cyrus Y H</au><au>Wong, Michael Y</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and characterization of greenish-blue emitting vinyl copolymer containing pyrene and triarylamine moieties</atitle><jtitle>Polymer international</jtitle><addtitle>Polym. Int</addtitle><date>2014-10</date><risdate>2014</risdate><volume>63</volume><issue>10</issue><spage>1797</spage><epage>1805</epage><pages>1797-1805</pages><issn>0959-8103</issn><eissn>1097-0126</eissn><coden>PLYIEI</coden><abstract>High yield, high Tg, soluble and greenish‐blue emitting vinyl copolymer. Two fluorescent monomers N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine (vinyl‐PyPA) and 1‐vinyl pyrene (VPy) were synthesized in good yields. A series of soluble conductive vinyl copolymers P(PyPA‐co‐VPy) containing vinyl‐PyPA and VPy moieties in different composition ratios were prepared by free radical solution polymerization. These copolymers showed high Tg (190−201 °C) and good thermal stability. The photoluminescence emission maxima of the copolymers were all in the range 474.5−478.5 nm, which was similar to the poly(N‐phenyl‐N‐(4‐vinylphenyl)pyren‐1‐amine) (P(PyPA)) (475 nm) but blue shifted compared with poly(1‐vinyl pyrene) (PVPy) (490.5 nm). The lifetime of the copolymers increased from 10.2 to 29.7 ns with an increase in pyrene content. The copolymers had higher quantum yields (0.51) than those of the homopolymers of P(PyPA) (0.48) and PVPy (0.13). The highest occupied molecular orbital of the copolymers remained relatively unchanged from P(PyPA), while the lowest unoccupied molecular orbital varied from −2.41 eV to −2.51 eV with an increase in pyrene ratio in the copolymers. The energy bandgaps of the copolymers (from 2.70 eV to 2.81 eV) were smaller than those of P(PyPA) (2.82 eV) and PVPy (3.47 eV). Two polymer light‐emitting diode (PLED) series were attempted including indium tin oxide (ITO) (fluorocarbon (CFx) treated)/P(PyPA‐co‐VPy)/LiF/Al and ITO(CFx treated)/P(PyPA‐co‐VPy)/1,3,5‐Tri(1‐phenyl‐1H‐benzo[d]imidazol‐2‐yl)phenyl (TPBi)/LiF/Al. The results suggested that the PyPA moiety is hole conducting and the PLEDs can achieve high luminance from 650 to 1150 cd m−2 (at 100 mA cm−2) only when an electron injecting layer TPBi is employed. © 2013 Society of Chemical Industry</abstract><cop>Chichester, UK</cop><pub>John Wiley &amp; Sons, Ltd</pub><doi>10.1002/pi.4682</doi><tpages>9</tpages></addata></record>
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subjects Aluminum
Applied sciences
Copolymers
Electronics
Emittance
Exact sciences and technology
free radical solution polymerization
Indium tin oxide
Luminance
Molecular orbitals
Optoelectronic devices
Organic polymers
Physicochemistry of polymers
poly(1-vinyl pyrene)
poly(N-phenyl-N-(4-vinylphenyl)pyren-1-amine)
Polymers with particular properties
Preparation, kinetics, thermodynamics, mechanism and catalysts
Pyrenes
Semiconductor electronics. Microelectronics. Optoelectronics. Solid state devices
vinyl copolymer
Vinyl copolymers
title Synthesis and characterization of greenish-blue emitting vinyl copolymer containing pyrene and triarylamine moieties
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