Pyranylidene indene-1,3-dione derivatives as an amorphous red electroluminescence material
Identifieur interne : 002669 ( Main/Repository ); précédent : 002668; suivant : 002670Pyranylidene indene-1,3-dione derivatives as an amorphous red electroluminescence material
Auteurs : RBID : Pascal:11-0411618Descripteurs français
- Pascal (Inist)
- Electroluminescence, Diode électroluminescente organique, Affichage écran plat, Source lumineuse, Impression à jet d'encre, Optimisation, Evaluation performance, Addition étain, Chromaticité, Luminance, Dione, Matériau amorphe, Molécule petite, Composé fluorescent, Composé organique, Oxyde d'indium, Styrènesulfonate polymère, Thiophène dérivé polymère, Mélange polymère, Fluorure de lithium, Electronique organique, 4272, ITO, LiF.
- Wicri :
- concept : Matériau amorphe.
English descriptors
- KwdEn :
- Amorphous material, Chromaticity, Dione, Electroluminescence, Flat panel displays, Fluorescent compound, Indium oxide, Ink jet printing, Light source, Lithium fluoride, Luminance, Optimization, Organic compounds, Organic electronics, Organic light emitting diodes, Performance evaluation, Polymer blends, Small molecule, Styrenesulfonate polymer, Thiophene derivative polymer, Tin addition.
Abstract
The organic light-emitting diode (OLED) has promising applications in flat-panel displays and novel light sources. Thus far, OLED structures have mostly been made by thermal evaporation in vacuum. An alternative approach is to use small molecules that form amorphous (glassy) structures from solutions. Such compounds can be used in ink-jet printing technologies and result in reduced OLED prices. We present an original red fluorescent organic compound 2-(2-(4-(bis(2-(trityloxy)ethyl)amino)styryl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1, 3(2H)-dione (ZWK1), and its derivative 2-(2,6-bis(4-(bis(2-(trityloxylethyl) amino)styryl)-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione (ZWK2), where the methyl group is replaced with a 4-substituted-styryl group. This change could improve the formation of glassy structures. The thickness of the electroluminescent layer in the device is optimized to the higher power efficiency and obtains: ITO/PEDOT:PSS (40 nm)/ZWK1 (95 nm)/LiF (1 nm)/Al (100 nm), and ITO/PEDOT:PSS (40 nm)/ZWK2 (85 nm)/LiF (1 nm)/Al (100 nm). The maximum of electroluminescence (EL) spectra for the device with the ZWK 1 compound is 667 nm, which corresponds to the CIE coordinates x = 0.65 and y = 0.34. The power and luminance efficiency at a luminance of 100 cd/m2 is 0.63 lm/W and 1.78 cd/A, respectively. Adding an additional 4-substituted-styryl group to the ZWK1 molecule shifts the maximum of EL spectra to the red region (705 nm) and decreases the efficiencies by one order.
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Pyranylidene indene-1,3-dione derivatives as an amorphous red electroluminescence material</title><author><name sortKey="Vembris, Aivars" uniqKey="Vembris A">Aivars Vembris</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>University of Latvia, Institute of Solid State Physics, 8 Kengaraga Str.</s1><s2>Riga 1063</s2><s3>LVA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ></inist:fA14><country>Lettonie</country><wicri:noRegion>Riga 1063</wicri:noRegion></affiliation></author><author><name sortKey="Porozovs, Martins" uniqKey="Porozovs M">Martins Porozovs</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>University of Latvia, Institute of Solid State Physics, 8 Kengaraga Str.</s1><s2>Riga 1063</s2><s3>LVA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ></inist:fA14><country>Lettonie</country><wicri:noRegion>Riga 1063</wicri:noRegion></affiliation></author><author><name sortKey="Muzikante, Inta" uniqKey="Muzikante I">Inta Muzikante</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>University of Latvia, Institute of Solid State Physics, 8 Kengaraga Str.</s1><s2>Riga 1063</s2><s3>LVA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ></inist:fA14><country>Lettonie</country><wicri:noRegion>Riga 1063</wicri:noRegion></affiliation></author><author><name sortKey="Kokars, Valdis" uniqKey="Kokars V">Valdis Kokars</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Riga Technical University, Institute of Applied Chemistry, 14/24 Azenes Str.</s1><s2>Riga 1048</s2><s3>LVA</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Lettonie</country><wicri:noRegion>Riga 1048</wicri:noRegion></affiliation></author><author><name sortKey="Zarins, Elmars" uniqKey="Zarins E">Elmars Zarins</name><affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Riga Technical University, Institute of Applied Chemistry, 14/24 Azenes Str.</s1><s2>Riga 1048</s2><s3>LVA</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></inist:fA14><country>Lettonie</country><wicri:noRegion>Riga 1048</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="inist">11-0411618</idno><date when="2011">2011</date><idno type="stanalyst">PASCAL 11-0411618 INIST</idno><idno type="RBID">Pascal:11-0411618</idno><idno type="wicri:Area/Main/Corpus">002965</idno><idno type="wicri:Area/Main/Repository">002669</idno></publicationStmt><seriesStmt><idno type="ISSN">0277-786X</idno><title level="j" type="abbreviated">Proc. SPIE Int. Soc. Opt. Eng.</title><title level="j" type="main">Proceedings of SPIE, the International Society for Optical Engineering</title></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amorphous material</term><term>Chromaticity</term><term>Dione</term><term>Electroluminescence</term><term>Flat panel displays</term><term>Fluorescent compound</term><term>Indium oxide</term><term>Ink jet printing</term><term>Light source</term><term>Lithium fluoride</term><term>Luminance</term><term>Optimization</term><term>Organic compounds</term><term>Organic electronics</term><term>Organic light emitting diodes</term><term>Performance evaluation</term><term>Polymer blends</term><term>Small molecule</term><term>Styrenesulfonate polymer</term><term>Thiophene derivative polymer</term><term>Tin addition</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Electroluminescence</term><term>Diode électroluminescente organique</term><term>Affichage écran plat</term><term>Source lumineuse</term><term>Impression à jet d'encre</term><term>Optimisation</term><term>Evaluation performance</term><term>Addition étain</term><term>Chromaticité</term><term>Luminance</term><term>Dione</term><term>Matériau amorphe</term><term>Molécule petite</term><term>Composé fluorescent</term><term>Composé organique</term><term>Oxyde d'indium</term><term>Styrènesulfonate polymère</term><term>Thiophène dérivé polymère</term><term>Mélange polymère</term><term>Fluorure de lithium</term><term>Electronique organique</term><term>4272</term><term>ITO</term><term>LiF</term></keywords><keywords scheme="Wicri" type="concept" xml:lang="fr"><term>Matériau amorphe</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The organic light-emitting diode (OLED) has promising applications in flat-panel displays and novel light sources. Thus far, OLED structures have mostly been made by thermal evaporation in vacuum. An alternative approach is to use small molecules that form amorphous (glassy) structures from solutions. Such compounds can be used in ink-jet printing technologies and result in reduced OLED prices. We present an original red fluorescent organic compound 2-(2-(4-(bis(2-(trityloxy)ethyl)amino)styryl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1, 3(2H)-dione (ZWK1), and its derivative 2-(2,6-bis(4-(bis(2-(trityloxylethyl) amino)styryl)-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione (ZWK2), where the methyl group is replaced with a 4-substituted-styryl group. This change could improve the formation of glassy structures. The thickness of the electroluminescent layer in the device is optimized to the higher power efficiency and obtains: ITO/PEDOT:PSS (40 nm)/ZWK1 (95 nm)/LiF (1 nm)/Al (100 nm), and ITO/PEDOT:PSS (40 nm)/ZWK2 (85 nm)/LiF (1 nm)/Al (100 nm). The maximum of electroluminescence (EL) spectra for the device with the ZWK 1 compound is 667 nm, which corresponds to the CIE coordinates x = 0.65 and y = 0.34. The power and luminance efficiency at a luminance of 100 cd/m<sup>2</sup> is 0.63 lm/W and 1.78 cd/A, respectively. Adding an additional 4-substituted-styryl group to the ZWK1 molecule shifts the maximum of EL spectra to the red region (705 nm) and decreases the efficiencies by one order.</div></front></TEI><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0277-786X</s0></fA01><fA02 i1="01"><s0>PSISDG</s0></fA02><fA03 i2="1"><s0>Proc. SPIE Int. Soc. Opt. Eng.</s0></fA03><fA05><s2>7776</s2></fA05><fA08 i1="01" i2="1" l="ENG"><s1>Pyranylidene indene-1,3-dione derivatives as an amorphous red electroluminescence material</s1></fA08><fA09 i1="01" i2="1" l="ENG"><s1>Organic light-emitting materials and devices XIV : 1-4 August, 2010, San Diego, California, USA</s1></fA09><fA11 i1="01" i2="1"><s1>VEMBRIS (Aivars)</s1></fA11><fA11 i1="02" i2="1"><s1>POROZOVS (Martins)</s1></fA11><fA11 i1="03" i2="1"><s1>MUZIKANTE (Inta)</s1></fA11><fA11 i1="04" i2="1"><s1>KOKARS (Valdis)</s1></fA11><fA11 i1="05" i2="1"><s1>ZARINS (Elmars)</s1></fA11><fA12 i1="01" i2="1"><s1>SO (Franky)</s1><s9>ed.</s9></fA12><fA12 i1="02" i2="1"><s1>ADACHI (Chihaya)</s1><s9>ed.</s9></fA12><fA14 i1="01"><s1>University of Latvia, Institute of Solid State Physics, 8 Kengaraga Str.</s1><s2>Riga 1063</s2><s3>LVA</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ></fA14><fA14 i1="02"><s1>Riga Technical University, Institute of Applied Chemistry, 14/24 Azenes Str.</s1><s2>Riga 1048</s2><s3>LVA</s3><sZ>4 aut.</sZ><sZ>5 aut.</sZ></fA14><fA18 i1="01" i2="1"><s1>Society of Photo-optical Instrumentation Engineers</s1><s3>USA</s3><s9>org-cong.</s9></fA18><fA20><s2>011001.1-011001.9</s2></fA20><fA21><s1>2011</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA25 i1="01"><s1>SPIE</s1><s2>Bellingham, Wash.</s2></fA25><fA26 i1="01"><s0>978-0-8194-8273-0</s0></fA26><fA43 i1="01"><s1>INIST</s1><s2>21760</s2><s5>354000174746450240</s5></fA43><fA44><s0>0000</s0><s1>© 2011 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>13 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>11-0411618</s0></fA47><fA60><s1>P</s1><s2>C</s2></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Proceedings of SPIE, the International Society for Optical Engineering</s0></fA64><fA66 i1="01"><s0>USA</s0></fA66><fC01 i1="01" l="ENG"><s0>The organic light-emitting diode (OLED) has promising applications in flat-panel displays and novel light sources. Thus far, OLED structures have mostly been made by thermal evaporation in vacuum. An alternative approach is to use small molecules that form amorphous (glassy) structures from solutions. Such compounds can be used in ink-jet printing technologies and result in reduced OLED prices. We present an original red fluorescent organic compound 2-(2-(4-(bis(2-(trityloxy)ethyl)amino)styryl)-6-methyl-4H-pyran-4-ylidene)-1H-indene-1, 3(2H)-dione (ZWK1), and its derivative 2-(2,6-bis(4-(bis(2-(trityloxylethyl) amino)styryl)-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione (ZWK2), where the methyl group is replaced with a 4-substituted-styryl group. This change could improve the formation of glassy structures. The thickness of the electroluminescent layer in the device is optimized to the higher power efficiency and obtains: ITO/PEDOT:PSS (40 nm)/ZWK1 (95 nm)/LiF (1 nm)/Al (100 nm), and ITO/PEDOT:PSS (40 nm)/ZWK2 (85 nm)/LiF (1 nm)/Al (100 nm). The maximum of electroluminescence (EL) spectra for the device with the ZWK 1 compound is 667 nm, which corresponds to the CIE coordinates x = 0.65 and y = 0.34. The power and luminance efficiency at a luminance of 100 cd/m<sup>2</sup> is 0.63 lm/W and 1.78 cd/A, respectively. Adding an additional 4-substituted-styryl group to the ZWK1 molecule shifts the maximum of EL spectra to the red region (705 nm) and decreases the efficiencies by one order.</s0></fC01><fC02 i1="01" i2="X"><s0>001D03F15</s0></fC02><fC02 i1="02" i2="X"><s0>001D03H</s0></fC02><fC02 i1="03" i2="3"><s0>001B40B72</s0></fC02><fC03 i1="01" i2="X" l="FRE"><s0>Electroluminescence</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="ENG"><s0>Electroluminescence</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="SPA"><s0>Electroluminiscencia</s0><s5>01</s5></fC03><fC03 i1="02" i2="3" l="FRE"><s0>Diode électroluminescente organique</s0><s5>02</s5></fC03><fC03 i1="02" i2="3" l="ENG"><s0>Organic light emitting diodes</s0><s5>02</s5></fC03><fC03 i1="03" i2="3" l="FRE"><s0>Affichage écran plat</s0><s5>03</s5></fC03><fC03 i1="03" i2="3" l="ENG"><s0>Flat panel displays</s0><s5>03</s5></fC03><fC03 i1="04" i2="X" l="FRE"><s0>Source lumineuse</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="ENG"><s0>Light source</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="SPA"><s0>Fuente luminosa</s0><s5>04</s5></fC03><fC03 i1="05" i2="X" l="FRE"><s0>Impression à jet d'encre</s0><s5>05</s5></fC03><fC03 i1="05" i2="X" l="ENG"><s0>Ink jet printing</s0><s5>05</s5></fC03><fC03 i1="05" i2="X" l="SPA"><s0>Impresión por chorro de tinta</s0><s5>05</s5></fC03><fC03 i1="06" i2="X" l="FRE"><s0>Optimisation</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="ENG"><s0>Optimization</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="SPA"><s0>Optimización</s0><s5>06</s5></fC03><fC03 i1="07" i2="X" l="FRE"><s0>Evaluation performance</s0><s5>07</s5></fC03><fC03 i1="07" i2="X" l="ENG"><s0>Performance evaluation</s0><s5>07</s5></fC03><fC03 i1="07" i2="X" l="SPA"><s0>Evaluación prestación</s0><s5>07</s5></fC03><fC03 i1="08" i2="X" l="FRE"><s0>Addition étain</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="ENG"><s0>Tin addition</s0><s5>08</s5></fC03><fC03 i1="08" i2="X" l="SPA"><s0>Adición estaño</s0><s5>08</s5></fC03><fC03 i1="09" i2="X" l="FRE"><s0>Chromaticité</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="ENG"><s0>Chromaticity</s0><s5>09</s5></fC03><fC03 i1="09" i2="X" l="SPA"><s0>Cromaticidad</s0><s5>09</s5></fC03><fC03 i1="10" i2="X" l="FRE"><s0>Luminance</s0><s5>10</s5></fC03><fC03 i1="10" i2="X" l="ENG"><s0>Luminance</s0><s5>10</s5></fC03><fC03 i1="10" i2="X" l="SPA"><s0>Luminancia</s0><s5>10</s5></fC03><fC03 i1="11" i2="3" l="FRE"><s0>Dione</s0><s5>22</s5></fC03><fC03 i1="11" i2="3" l="ENG"><s0>Dione</s0><s5>22</s5></fC03><fC03 i1="12" i2="X" l="FRE"><s0>Matériau amorphe</s0><s5>23</s5></fC03><fC03 i1="12" i2="X" l="ENG"><s0>Amorphous material</s0><s5>23</s5></fC03><fC03 i1="12" i2="X" l="SPA"><s0>Material amorfo</s0><s5>23</s5></fC03><fC03 i1="13" i2="X" l="FRE"><s0>Molécule petite</s0><s5>24</s5></fC03><fC03 i1="13" i2="X" l="ENG"><s0>Small molecule</s0><s5>24</s5></fC03><fC03 i1="13" i2="X" l="SPA"><s0>Molécula pequeña</s0><s5>24</s5></fC03><fC03 i1="14" i2="X" l="FRE"><s0>Composé fluorescent</s0><s5>25</s5></fC03><fC03 i1="14" i2="X" l="ENG"><s0>Fluorescent compound</s0><s5>25</s5></fC03><fC03 i1="14" i2="X" l="SPA"><s0>Compuesto fluorescente</s0><s5>25</s5></fC03><fC03 i1="15" i2="X" l="FRE"><s0>Composé organique</s0><s2>NA</s2><s5>26</s5></fC03><fC03 i1="15" i2="X" l="ENG"><s0>Organic compounds</s0><s2>NA</s2><s5>26</s5></fC03><fC03 i1="15" i2="X" l="SPA"><s0>Compuesto orgánico</s0><s2>NA</s2><s5>26</s5></fC03><fC03 i1="16" i2="X" l="FRE"><s0>Oxyde d'indium</s0><s5>27</s5></fC03><fC03 i1="16" i2="X" l="ENG"><s0>Indium oxide</s0><s5>27</s5></fC03><fC03 i1="16" i2="X" l="SPA"><s0>Indio óxido</s0><s5>27</s5></fC03><fC03 i1="17" i2="X" l="FRE"><s0>Styrènesulfonate polymère</s0><s2>NK</s2><s5>28</s5></fC03><fC03 i1="17" i2="X" l="ENG"><s0>Styrenesulfonate polymer</s0><s2>NK</s2><s5>28</s5></fC03><fC03 i1="17" i2="X" l="SPA"><s0>Estireno sulfonato polímero</s0><s2>NK</s2><s5>28</s5></fC03><fC03 i1="18" i2="X" l="FRE"><s0>Thiophène dérivé 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l="FRE"><s0>LiF</s0><s4>INC</s4><s5>83</s5></fC03><fC07 i1="01" i2="X" l="FRE"><s0>Dispositif optoélectronique</s0><s5>11</s5></fC07><fC07 i1="01" i2="X" l="ENG"><s0>Optoelectronic device</s0><s5>11</s5></fC07><fC07 i1="01" i2="X" l="SPA"><s0>Dispositivo optoelectrónico</s0><s5>11</s5></fC07><fN21><s1>283</s1></fN21><fN44 i1="01"><s1>OTO</s1></fN44><fN82><s1>OTO</s1></fN82></pA><pR><fA30 i1="01" i2="1" l="ENG"><s1>Organic light-emitting materials and devices. 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