A hybridized local and charge transfer excited state for solution-processed non-doped green electroluminescence based on oligo(-phenyleneethynylene)
We herein report a new highly efficient green emissive hot-exciton molecule, 1,4-bis((4′-diphenylamino-3-cyano-[1,1′-biphenyl]-4-yl)ethynyl)-2,5-bis(2-ethylhexyloxy)benzene ( 2EHO-TPA-CNPE ) that consists of an extended D′-π′-A-π-D-π-A-π′-D′ molecular π-system with diphenylamino end units (D′) and e...
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creator | Usta, Hakan Alimli, Dilek Ozdemir, Resul Tekin, Emine Alkan, Fahri Kacar, Rifat Altas, Ahu Galen Dabak, Salih Gürek, Ay e Gül Mutlugun, Evren Yazici, Ahmet Faruk Can, Ayse |
description | We herein report a new highly efficient green emissive hot-exciton molecule, 1,4-bis((4′-diphenylamino-3-cyano-[1,1′-biphenyl]-4-yl)ethynyl)-2,5-bis(2-ethylhexyloxy)benzene (
2EHO-TPA-CNPE
) that consists of an extended D′-π′-A-π-D-π-A-π′-D′ molecular π-system with diphenylamino end units (D′) and ethynylene/phenylene spacers (π/π′). The new molecule exhibits high photoluminescence (PL) quantum efficiencies (
Φ
PL
= 0.95 (solution) and 0.45 (spin-coated neat thin-film)), and a strong PL solvatochromic behavior revealing significant changes in excited state energies/characteristics (locally excited (LE) → hybridized local and charge transfer (HLCT) → charge-transfer (CT)) depending on solvent polarity. Highly efficient (radiative exciton yield (
η
r
) = 50-59% > 25%) green-emitting OLEDs were fabricated in a conventional device architecture by employing (non-)doped thin-films reaching a maximum current efficiency (CE
max
) of 12.0 cd A
−1
and a maximum external quantum efficiency (EQE
max
) of 5.5%. The emission profile of the non-doped OLED has CIE 1976 (
u
′,
v
′) chromaticity coordinates of (0.10, 0.55) corresponding to a night vision imaging system (NVIS) compatible Green A region.
2EHO-TPA-CNPE
-based OLED devices of industrial relevance were also fabricated by ink-jet printing the emissive layer and by fabricating an inverted architecture, which possessed respectable device performances of 2.4-6.1 cd A
−1
. The solid-state solvation effect in OLED devices yields HLCT electronic behavior resulting in high
η
r
's, which is confirmed by TDDFT to originate from energetically/spatially favorable reverse intersystem crossings (RISCs) (T
2/3
→ S
1
). As a unique observation, delayed fluorescence due to this RISC was evident in the PL decay lifetime measurement with a ns-scale lifetime of ∼10 ns. These results clearly allow a better understanding of the structure-photophysical property-electroluminescence relationships in this new class of oligo(
p
-phenyleneethynylene)-based hot-exciton molecules, and it could open up new opportunities for high-performance solution-processed optoelectronic/sensing applications.
A novel oligo(
p
-phenyleneethynylene)-based hot-exciton molecule with hybridized local and charge transfer (HLCT) excited states was developed to yield high radiative exciton yields in OLEDs. |
doi_str_mv | 10.1039/d0tc01266a |
format | Article |
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2EHO-TPA-CNPE
) that consists of an extended D′-π′-A-π-D-π-A-π′-D′ molecular π-system with diphenylamino end units (D′) and ethynylene/phenylene spacers (π/π′). The new molecule exhibits high photoluminescence (PL) quantum efficiencies (
Φ
PL
= 0.95 (solution) and 0.45 (spin-coated neat thin-film)), and a strong PL solvatochromic behavior revealing significant changes in excited state energies/characteristics (locally excited (LE) → hybridized local and charge transfer (HLCT) → charge-transfer (CT)) depending on solvent polarity. Highly efficient (radiative exciton yield (
η
r
) = 50-59% > 25%) green-emitting OLEDs were fabricated in a conventional device architecture by employing (non-)doped thin-films reaching a maximum current efficiency (CE
max
) of 12.0 cd A
−1
and a maximum external quantum efficiency (EQE
max
) of 5.5%. The emission profile of the non-doped OLED has CIE 1976 (
u
′,
v
′) chromaticity coordinates of (0.10, 0.55) corresponding to a night vision imaging system (NVIS) compatible Green A region.
2EHO-TPA-CNPE
-based OLED devices of industrial relevance were also fabricated by ink-jet printing the emissive layer and by fabricating an inverted architecture, which possessed respectable device performances of 2.4-6.1 cd A
−1
. The solid-state solvation effect in OLED devices yields HLCT electronic behavior resulting in high
η
r
's, which is confirmed by TDDFT to originate from energetically/spatially favorable reverse intersystem crossings (RISCs) (T
2/3
→ S
1
). As a unique observation, delayed fluorescence due to this RISC was evident in the PL decay lifetime measurement with a ns-scale lifetime of ∼10 ns. These results clearly allow a better understanding of the structure-photophysical property-electroluminescence relationships in this new class of oligo(
p
-phenyleneethynylene)-based hot-exciton molecules, and it could open up new opportunities for high-performance solution-processed optoelectronic/sensing applications.
A novel oligo(
p
-phenyleneethynylene)-based hot-exciton molecule with hybridized local and charge transfer (HLCT) excited states was developed to yield high radiative exciton yields in OLEDs.</description><identifier>ISSN: 2050-7526</identifier><identifier>EISSN: 2050-7534</identifier><identifier>DOI: 10.1039/d0tc01266a</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Absorption spectra ; Benzene ; Charge transfer ; Chemical synthesis ; Chromaticity ; Computer architecture ; Coupling (molecular) ; Current density ; Current efficiency ; Efficiency ; Electroluminescence ; Electronic devices ; Emissivity ; Excitation ; Excitons ; Fluorescence ; Inkjet printing ; Molecular orbitals ; Night vision ; Photoluminescence ; Polarity ; Quantum efficiency ; Solvation ; Solvents ; Thin films</subject><ispartof>Journal of materials chemistry. C, Materials for optical and electronic devices, 2020-06, Vol.8 (24), p.847-86</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c365t-8a0964cfe3481c27aa9c75e40362535e1dd6e1b32e03ad5eca731ae3fa7997163</citedby><cites>FETCH-LOGICAL-c365t-8a0964cfe3481c27aa9c75e40362535e1dd6e1b32e03ad5eca731ae3fa7997163</cites><orcidid>0000-0002-8565-2424 ; 0000-0003-4564-9447 ; 0000-0003-3715-5594 ; 0000-0002-7957-110X ; 0000-0002-0618-1979 ; 0000-0001-6014-8072</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Usta, Hakan</creatorcontrib><creatorcontrib>Alimli, Dilek</creatorcontrib><creatorcontrib>Ozdemir, Resul</creatorcontrib><creatorcontrib>Tekin, Emine</creatorcontrib><creatorcontrib>Alkan, Fahri</creatorcontrib><creatorcontrib>Kacar, Rifat</creatorcontrib><creatorcontrib>Altas, Ahu Galen</creatorcontrib><creatorcontrib>Dabak, Salih</creatorcontrib><creatorcontrib>Gürek, Ay e Gül</creatorcontrib><creatorcontrib>Mutlugun, Evren</creatorcontrib><creatorcontrib>Yazici, Ahmet Faruk</creatorcontrib><creatorcontrib>Can, Ayse</creatorcontrib><title>A hybridized local and charge transfer excited state for solution-processed non-doped green electroluminescence based on oligo(-phenyleneethynylene)</title><title>Journal of materials chemistry. C, Materials for optical and electronic devices</title><description>We herein report a new highly efficient green emissive hot-exciton molecule, 1,4-bis((4′-diphenylamino-3-cyano-[1,1′-biphenyl]-4-yl)ethynyl)-2,5-bis(2-ethylhexyloxy)benzene (
2EHO-TPA-CNPE
) that consists of an extended D′-π′-A-π-D-π-A-π′-D′ molecular π-system with diphenylamino end units (D′) and ethynylene/phenylene spacers (π/π′). The new molecule exhibits high photoluminescence (PL) quantum efficiencies (
Φ
PL
= 0.95 (solution) and 0.45 (spin-coated neat thin-film)), and a strong PL solvatochromic behavior revealing significant changes in excited state energies/characteristics (locally excited (LE) → hybridized local and charge transfer (HLCT) → charge-transfer (CT)) depending on solvent polarity. Highly efficient (radiative exciton yield (
η
r
) = 50-59% > 25%) green-emitting OLEDs were fabricated in a conventional device architecture by employing (non-)doped thin-films reaching a maximum current efficiency (CE
max
) of 12.0 cd A
−1
and a maximum external quantum efficiency (EQE
max
) of 5.5%. The emission profile of the non-doped OLED has CIE 1976 (
u
′,
v
′) chromaticity coordinates of (0.10, 0.55) corresponding to a night vision imaging system (NVIS) compatible Green A region.
2EHO-TPA-CNPE
-based OLED devices of industrial relevance were also fabricated by ink-jet printing the emissive layer and by fabricating an inverted architecture, which possessed respectable device performances of 2.4-6.1 cd A
−1
. The solid-state solvation effect in OLED devices yields HLCT electronic behavior resulting in high
η
r
's, which is confirmed by TDDFT to originate from energetically/spatially favorable reverse intersystem crossings (RISCs) (T
2/3
→ S
1
). As a unique observation, delayed fluorescence due to this RISC was evident in the PL decay lifetime measurement with a ns-scale lifetime of ∼10 ns. These results clearly allow a better understanding of the structure-photophysical property-electroluminescence relationships in this new class of oligo(
p
-phenyleneethynylene)-based hot-exciton molecules, and it could open up new opportunities for high-performance solution-processed optoelectronic/sensing applications.
A novel oligo(
p
-phenyleneethynylene)-based hot-exciton molecule with hybridized local and charge transfer (HLCT) excited states was developed to yield high radiative exciton yields in OLEDs.</description><subject>Absorption spectra</subject><subject>Benzene</subject><subject>Charge transfer</subject><subject>Chemical synthesis</subject><subject>Chromaticity</subject><subject>Computer architecture</subject><subject>Coupling (molecular)</subject><subject>Current density</subject><subject>Current efficiency</subject><subject>Efficiency</subject><subject>Electroluminescence</subject><subject>Electronic devices</subject><subject>Emissivity</subject><subject>Excitation</subject><subject>Excitons</subject><subject>Fluorescence</subject><subject>Inkjet printing</subject><subject>Molecular orbitals</subject><subject>Night vision</subject><subject>Photoluminescence</subject><subject>Polarity</subject><subject>Quantum efficiency</subject><subject>Solvation</subject><subject>Solvents</subject><subject>Thin films</subject><issn>2050-7526</issn><issn>2050-7534</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90U1PwyAcBnBiNHHRXbybYLyoSRVKoetxma_JEi_z3DD4d-3SQQWWWD-HH1hmzbzJhYfwC4QHhM4ouaWEFXeaBEVoKoQ8QKOUcJLknGWH-5yKYzT2fk3imFAxEcUIfU1x3S9do5tP0Li1SrZYGo1VLd0KcHDS-Aochg_VhCh8kAFwZR32tt2Gxpqkc1aB93HTxJW2XUwrB2AwtKCCi27TGPAKjAK8lDtpDbZts7JXSVeD6VswAKHuh3R9io4q2XoY_84n6O3xYTF7TuavTy-z6TxRTPCQTCQpRKYqYNmEqjSXslA5h4wwkXLGgWotgC5ZCoRJzUHJnFEJrJJ5UeRUsBN0OZwbn_C-BR_Ktd06E68s0ywWlHGaFlHdDEo5672Dquxcs5GuLykpd8WX92Qx-yl-GvHFgJ1Xe_f3MWWnq2jO_zPsGyI2jho</recordid><startdate>20200628</startdate><enddate>20200628</enddate><creator>Usta, Hakan</creator><creator>Alimli, Dilek</creator><creator>Ozdemir, Resul</creator><creator>Tekin, Emine</creator><creator>Alkan, Fahri</creator><creator>Kacar, Rifat</creator><creator>Altas, Ahu Galen</creator><creator>Dabak, Salih</creator><creator>Gürek, Ay e Gül</creator><creator>Mutlugun, Evren</creator><creator>Yazici, Ahmet Faruk</creator><creator>Can, Ayse</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SP</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-8565-2424</orcidid><orcidid>https://orcid.org/0000-0003-4564-9447</orcidid><orcidid>https://orcid.org/0000-0003-3715-5594</orcidid><orcidid>https://orcid.org/0000-0002-7957-110X</orcidid><orcidid>https://orcid.org/0000-0002-0618-1979</orcidid><orcidid>https://orcid.org/0000-0001-6014-8072</orcidid></search><sort><creationdate>20200628</creationdate><title>A hybridized local and charge transfer excited state for solution-processed non-doped green electroluminescence based on oligo(-phenyleneethynylene)</title><author>Usta, Hakan ; Alimli, Dilek ; Ozdemir, Resul ; Tekin, Emine ; Alkan, Fahri ; Kacar, Rifat ; Altas, Ahu Galen ; Dabak, Salih ; Gürek, Ay e Gül ; Mutlugun, Evren ; Yazici, Ahmet Faruk ; Can, Ayse</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c365t-8a0964cfe3481c27aa9c75e40362535e1dd6e1b32e03ad5eca731ae3fa7997163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Absorption spectra</topic><topic>Benzene</topic><topic>Charge transfer</topic><topic>Chemical synthesis</topic><topic>Chromaticity</topic><topic>Computer architecture</topic><topic>Coupling (molecular)</topic><topic>Current density</topic><topic>Current efficiency</topic><topic>Efficiency</topic><topic>Electroluminescence</topic><topic>Electronic devices</topic><topic>Emissivity</topic><topic>Excitation</topic><topic>Excitons</topic><topic>Fluorescence</topic><topic>Inkjet printing</topic><topic>Molecular orbitals</topic><topic>Night vision</topic><topic>Photoluminescence</topic><topic>Polarity</topic><topic>Quantum efficiency</topic><topic>Solvation</topic><topic>Solvents</topic><topic>Thin films</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Usta, Hakan</creatorcontrib><creatorcontrib>Alimli, Dilek</creatorcontrib><creatorcontrib>Ozdemir, Resul</creatorcontrib><creatorcontrib>Tekin, Emine</creatorcontrib><creatorcontrib>Alkan, Fahri</creatorcontrib><creatorcontrib>Kacar, Rifat</creatorcontrib><creatorcontrib>Altas, Ahu Galen</creatorcontrib><creatorcontrib>Dabak, Salih</creatorcontrib><creatorcontrib>Gürek, Ay e Gül</creatorcontrib><creatorcontrib>Mutlugun, Evren</creatorcontrib><creatorcontrib>Yazici, Ahmet Faruk</creatorcontrib><creatorcontrib>Can, Ayse</creatorcontrib><collection>CrossRef</collection><collection>Electronics & Communications Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of materials chemistry. C, Materials for optical and electronic devices</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Usta, Hakan</au><au>Alimli, Dilek</au><au>Ozdemir, Resul</au><au>Tekin, Emine</au><au>Alkan, Fahri</au><au>Kacar, Rifat</au><au>Altas, Ahu Galen</au><au>Dabak, Salih</au><au>Gürek, Ay e Gül</au><au>Mutlugun, Evren</au><au>Yazici, Ahmet Faruk</au><au>Can, Ayse</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A hybridized local and charge transfer excited state for solution-processed non-doped green electroluminescence based on oligo(-phenyleneethynylene)</atitle><jtitle>Journal of materials chemistry. C, Materials for optical and electronic devices</jtitle><date>2020-06-28</date><risdate>2020</risdate><volume>8</volume><issue>24</issue><spage>847</spage><epage>86</epage><pages>847-86</pages><issn>2050-7526</issn><eissn>2050-7534</eissn><abstract>We herein report a new highly efficient green emissive hot-exciton molecule, 1,4-bis((4′-diphenylamino-3-cyano-[1,1′-biphenyl]-4-yl)ethynyl)-2,5-bis(2-ethylhexyloxy)benzene (
2EHO-TPA-CNPE
) that consists of an extended D′-π′-A-π-D-π-A-π′-D′ molecular π-system with diphenylamino end units (D′) and ethynylene/phenylene spacers (π/π′). The new molecule exhibits high photoluminescence (PL) quantum efficiencies (
Φ
PL
= 0.95 (solution) and 0.45 (spin-coated neat thin-film)), and a strong PL solvatochromic behavior revealing significant changes in excited state energies/characteristics (locally excited (LE) → hybridized local and charge transfer (HLCT) → charge-transfer (CT)) depending on solvent polarity. Highly efficient (radiative exciton yield (
η
r
) = 50-59% > 25%) green-emitting OLEDs were fabricated in a conventional device architecture by employing (non-)doped thin-films reaching a maximum current efficiency (CE
max
) of 12.0 cd A
−1
and a maximum external quantum efficiency (EQE
max
) of 5.5%. The emission profile of the non-doped OLED has CIE 1976 (
u
′,
v
′) chromaticity coordinates of (0.10, 0.55) corresponding to a night vision imaging system (NVIS) compatible Green A region.
2EHO-TPA-CNPE
-based OLED devices of industrial relevance were also fabricated by ink-jet printing the emissive layer and by fabricating an inverted architecture, which possessed respectable device performances of 2.4-6.1 cd A
−1
. The solid-state solvation effect in OLED devices yields HLCT electronic behavior resulting in high
η
r
's, which is confirmed by TDDFT to originate from energetically/spatially favorable reverse intersystem crossings (RISCs) (T
2/3
→ S
1
). As a unique observation, delayed fluorescence due to this RISC was evident in the PL decay lifetime measurement with a ns-scale lifetime of ∼10 ns. These results clearly allow a better understanding of the structure-photophysical property-electroluminescence relationships in this new class of oligo(
p
-phenyleneethynylene)-based hot-exciton molecules, and it could open up new opportunities for high-performance solution-processed optoelectronic/sensing applications.
A novel oligo(
p
-phenyleneethynylene)-based hot-exciton molecule with hybridized local and charge transfer (HLCT) excited states was developed to yield high radiative exciton yields in OLEDs.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d0tc01266a</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-8565-2424</orcidid><orcidid>https://orcid.org/0000-0003-4564-9447</orcidid><orcidid>https://orcid.org/0000-0003-3715-5594</orcidid><orcidid>https://orcid.org/0000-0002-7957-110X</orcidid><orcidid>https://orcid.org/0000-0002-0618-1979</orcidid><orcidid>https://orcid.org/0000-0001-6014-8072</orcidid></addata></record> |
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ispartof | Journal of materials chemistry. C, Materials for optical and electronic devices, 2020-06, Vol.8 (24), p.847-86 |
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language | eng |
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source | Royal Society Of Chemistry Journals 2008- |
subjects | Absorption spectra Benzene Charge transfer Chemical synthesis Chromaticity Computer architecture Coupling (molecular) Current density Current efficiency Efficiency Electroluminescence Electronic devices Emissivity Excitation Excitons Fluorescence Inkjet printing Molecular orbitals Night vision Photoluminescence Polarity Quantum efficiency Solvation Solvents Thin films |
title | A hybridized local and charge transfer excited state for solution-processed non-doped green electroluminescence based on oligo(-phenyleneethynylene) |
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