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Synthesis and electroluminescent properties of highly efficient anthracene derivatives with bulky side groups

Identifieur interne : 000D09 ( Chine/Analysis ); précédent : 000D08; suivant : 000D10

Synthesis and electroluminescent properties of highly efficient anthracene derivatives with bulky side groups

Auteurs : RBID : Pascal:09-0356996

Descripteurs français

English descriptors

Abstract

Three new asymmetric light emitting organic compounds were synthesized with diphenylamine or triphenylamine side groups; 10-(3,5-diphenylphenyl)-N,N-diphenylanthracen-9-amine (MADa), 4-(10-(3,5-diphenylphenyl)anthracen-9-yl)-N,N-diphenylaniline (MATa), and 4-(10-(3',5'-diphenylbiphenyl-4-yl)anthracen-9-yl)-N,N-diphenylaniline (TATa). MATa and TATa had a PLmax at 463 nm in the blue region, and MADa had a PLmax at 498 nm. MADa and MATa had Tg values greater than 120 °C, and TATa had a Tg of 139 °C. EL devices containing the synthesized compounds were fabricated in the configuration: ITO/4,4', 4"-tris(N-(2-naphthyl)-N-phenyl-amino)-triphenylamine (2-TNATA) (60 nm)/N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidine (NPB) (15 nm)/MADa or MATa or TATa or 9,1 0-di(2'-naphthyl)anthracene (MADN) (30 nm)/8-hydroxyquinoline aluminum (Alq3) (30 nm)/LiF (1 nm)/Al (200 nm). The efficiency and color coordinate values (respectively) were 10.3 cd/A and (0.199, 0.152: bluish-green) for the MADa device, 4.67 cd/A and (0.151, 0.177) for the MATa device, and 6.07 cd/A and (0.149, 0.177) for the TATa device. The TATa device had a high external quantum efficiency (EQE) of 6.19%, and its luminance and power efficiencies and life-time were more than twice those of the MADN device.

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Pascal:09-0356996

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<title xml:lang="en" level="a">Synthesis and electroluminescent properties of highly efficient anthracene derivatives with bulky side groups</title>
<author>
<name sortKey="Kim, Soo Kang" uniqKey="Kim S">Soo-Kang Kim</name>
<affiliation wicri:level="1">
<inist:fA14 i1="01">
<s1>Department of Chemistry/Display Research Center, The Catholic University of Korea</s1>
<s2>Bucheon, Kyunggi 420-743</s2>
<s3>KOR</s3>
<sZ>1 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>7 aut.</sZ>
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<country>Corée du Sud</country>
<wicri:noRegion>Bucheon, Kyunggi 420-743</wicri:noRegion>
</affiliation>
</author>
<author>
<name>BING YANG</name>
<affiliation wicri:level="1">
<inist:fA14 i1="02">
<s1>State Key Laboratory of Supramolecular Structure and Materials, Jilin University</s1>
<s2>Changchun 130012</s2>
<s3>CHN</s3>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
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<country>République populaire de Chine</country>
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<settlement type="city">Changchun</settlement>
<region type="province">Jilin</region>
<region type="groupement">Dongbei</region>
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<author>
<name sortKey="Park, Young Il" uniqKey="Park Y">Young-Il Park</name>
<affiliation wicri:level="1">
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<s1>Department of Chemistry/Display Research Center, The Catholic University of Korea</s1>
<s2>Bucheon, Kyunggi 420-743</s2>
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<sZ>1 aut.</sZ>
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<country>Corée du Sud</country>
<wicri:noRegion>Bucheon, Kyunggi 420-743</wicri:noRegion>
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<author>
<name>YUGUANG MA</name>
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<s1>State Key Laboratory of Supramolecular Structure and Materials, Jilin University</s1>
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<author>
<name sortKey="Lee, Jun Yeob" uniqKey="Lee J">Jun-Yeob Lee</name>
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<s1>Department of Polymer Engineering, Dankook University</s1>
<s2>Yongin, Kyung-gi 448-701</s2>
<s3>KOR</s3>
<sZ>5 aut.</sZ>
</inist:fA14>
<country>Corée du Sud</country>
<wicri:noRegion>Yongin, Kyung-gi 448-701</wicri:noRegion>
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<author>
<name sortKey="Kim, Hyoung Juhn" uniqKey="Kim H">Hyoung-Juhn Kim</name>
<affiliation wicri:level="1">
<inist:fA14 i1="04">
<s1>Center for Fuel Cell Research, Korea Institute of Science and Technology</s1>
<s2>Hawolgok, Seoul 136-791</s2>
<s3>KOR</s3>
<sZ>6 aut.</sZ>
</inist:fA14>
<country>Corée du Sud</country>
<wicri:noRegion>Hawolgok, Seoul 136-791</wicri:noRegion>
</affiliation>
</author>
<author>
<name sortKey="Park, Jongwook" uniqKey="Park J">Jongwook Park</name>
<affiliation wicri:level="1">
<inist:fA14 i1="01">
<s1>Department of Chemistry/Display Research Center, The Catholic University of Korea</s1>
<s2>Bucheon, Kyunggi 420-743</s2>
<s3>KOR</s3>
<sZ>1 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>7 aut.</sZ>
</inist:fA14>
<country>Corée du Sud</country>
<wicri:noRegion>Bucheon, Kyunggi 420-743</wicri:noRegion>
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<idno type="inist">09-0356996</idno>
<date when="2009">2009</date>
<idno type="stanalyst">PASCAL 09-0356996 INIST</idno>
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<term>Aluminium</term>
<term>Aluminium complex</term>
<term>Anthracene</term>
<term>Anthracene derivatives</term>
<term>Blue light</term>
<term>Chromaticity</term>
<term>Electroluminescent device</term>
<term>Indium oxide</term>
<term>Lithium fluoride</term>
<term>Luminance</term>
<term>Luminescence</term>
<term>Optoelectronic device</term>
<term>Organic compounds</term>
<term>Organic electronics</term>
<term>Organic light emitting diodes</term>
<term>Performance evaluation</term>
<term>Polycyclic aromatic amines</term>
<term>Quantum yield</term>
<term>Tin oxide</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr">
<term>Composé organique</term>
<term>Dispositif électroluminescent</term>
<term>Aluminium</term>
<term>Evaluation performance</term>
<term>Chromaticité</term>
<term>Rendement quantique</term>
<term>Luminance</term>
<term>Luminescence</term>
<term>Diode électroluminescente organique</term>
<term>Lumière bleue</term>
<term>Dérivé de l'anthracène</term>
<term>Oxyde d'indium</term>
<term>Oxyde d'étain</term>
<term>Amine aromatique polycyclique</term>
<term>Anthracène</term>
<term>Quinoléin-8-ol</term>
<term>Complexe d'aluminium</term>
<term>Fluorure de lithium</term>
<term>Dispositif optoélectronique</term>
<term>Electronique organique</term>
<term>ITO</term>
<term>LiF</term>
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<term>Aluminium</term>
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<front>
<div type="abstract" xml:lang="en">Three new asymmetric light emitting organic compounds were synthesized with diphenylamine or triphenylamine side groups; 10-(3,5-diphenylphenyl)-N,N-diphenylanthracen-9-amine (MADa), 4-(10-(3,5-diphenylphenyl)anthracen-9-yl)-N,N-diphenylaniline (MATa), and 4-(10-(3',5'-diphenylbiphenyl-4-yl)anthracen-9-yl)-N,N-diphenylaniline (TATa). MATa and TATa had a PL
<sub>max</sub>
at 463 nm in the blue region, and MADa had a PL
<sub>max</sub>
at 498 nm. MADa and MATa had T
<sub>g</sub>
values greater than 120 °C, and TATa had a T
<sub>g</sub>
of 139 °C. EL devices containing the synthesized compounds were fabricated in the configuration: ITO/4,4', 4"-tris(N-(2-naphthyl)-N-phenyl-amino)-triphenylamine (2-TNATA) (60 nm)/N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidine (NPB) (15 nm)/MADa or MATa or TATa or 9,1 0-di(2'-naphthyl)anthracene (MADN) (30 nm)/8-hydroxyquinoline aluminum (Alq
<sub>3</sub>
) (30 nm)/LiF (1 nm)/Al (200 nm). The efficiency and color coordinate values (respectively) were 10.3 cd/A and (0.199, 0.152: bluish-green) for the MADa device, 4.67 cd/A and (0.151, 0.177) for the MATa device, and 6.07 cd/A and (0.149, 0.177) for the TATa device. The TATa device had a high external quantum efficiency (EQE) of 6.19%, and its luminance and power efficiencies and life-time were more than twice those of the MADN device.</div>
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<s1>LEE (Jun-Yeob)</s1>
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<s1>Department of Chemistry/Display Research Center, The Catholic University of Korea</s1>
<s2>Bucheon, Kyunggi 420-743</s2>
<s3>KOR</s3>
<sZ>1 aut.</sZ>
<sZ>3 aut.</sZ>
<sZ>7 aut.</sZ>
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<fA14 i1="02">
<s1>State Key Laboratory of Supramolecular Structure and Materials, Jilin University</s1>
<s2>Changchun 130012</s2>
<s3>CHN</s3>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
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<fA14 i1="03">
<s1>Department of Polymer Engineering, Dankook University</s1>
<s2>Yongin, Kyung-gi 448-701</s2>
<s3>KOR</s3>
<sZ>5 aut.</sZ>
</fA14>
<fA14 i1="04">
<s1>Center for Fuel Cell Research, Korea Institute of Science and Technology</s1>
<s2>Hawolgok, Seoul 136-791</s2>
<s3>KOR</s3>
<sZ>6 aut.</sZ>
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<s1>P</s1>
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<s0>NLD</s0>
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<fC01 i1="01" l="ENG">
<s0>Three new asymmetric light emitting organic compounds were synthesized with diphenylamine or triphenylamine side groups; 10-(3,5-diphenylphenyl)-N,N-diphenylanthracen-9-amine (MADa), 4-(10-(3,5-diphenylphenyl)anthracen-9-yl)-N,N-diphenylaniline (MATa), and 4-(10-(3',5'-diphenylbiphenyl-4-yl)anthracen-9-yl)-N,N-diphenylaniline (TATa). MATa and TATa had a PL
<sub>max</sub>
at 463 nm in the blue region, and MADa had a PL
<sub>max</sub>
at 498 nm. MADa and MATa had T
<sub>g</sub>
values greater than 120 °C, and TATa had a T
<sub>g</sub>
of 139 °C. EL devices containing the synthesized compounds were fabricated in the configuration: ITO/4,4', 4"-tris(N-(2-naphthyl)-N-phenyl-amino)-triphenylamine (2-TNATA) (60 nm)/N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)benzidine (NPB) (15 nm)/MADa or MATa or TATa or 9,1 0-di(2'-naphthyl)anthracene (MADN) (30 nm)/8-hydroxyquinoline aluminum (Alq
<sub>3</sub>
) (30 nm)/LiF (1 nm)/Al (200 nm). The efficiency and color coordinate values (respectively) were 10.3 cd/A and (0.199, 0.152: bluish-green) for the MADa device, 4.67 cd/A and (0.151, 0.177) for the MATa device, and 6.07 cd/A and (0.149, 0.177) for the TATa device. The TATa device had a high external quantum efficiency (EQE) of 6.19%, and its luminance and power efficiencies and life-time were more than twice those of the MADN device.</s0>
</fC01>
<fC02 i1="01" i2="X">
<s0>001D03F15</s0>
</fC02>
<fC03 i1="01" i2="X" l="FRE">
<s0>Composé organique</s0>
<s2>NA</s2>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="ENG">
<s0>Organic compounds</s0>
<s2>NA</s2>
<s5>01</s5>
</fC03>
<fC03 i1="01" i2="X" l="SPA">
<s0>Compuesto orgánico</s0>
<s2>NA</s2>
<s5>01</s5>
</fC03>
<fC03 i1="02" i2="X" l="FRE">
<s0>Dispositif électroluminescent</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="ENG">
<s0>Electroluminescent device</s0>
<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA">
<s0>Dispositivo electroluminiscente</s0>
<s5>02</s5>
</fC03>
<fC03 i1="03" i2="X" l="FRE">
<s0>Aluminium</s0>
<s2>NC</s2>
<s2>FR</s2>
<s2>FX</s2>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG">
<s0>Aluminium</s0>
<s2>NC</s2>
<s2>FR</s2>
<s2>FX</s2>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA">
<s0>Aluminio</s0>
<s2>NC</s2>
<s2>FR</s2>
<s2>FX</s2>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE">
<s0>Evaluation performance</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG">
<s0>Performance evaluation</s0>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA">
<s0>Evaluación prestación</s0>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE">
<s0>Chromaticité</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG">
<s0>Chromaticity</s0>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA">
<s0>Cromaticidad</s0>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE">
<s0>Rendement quantique</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG">
<s0>Quantum yield</s0>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA">
<s0>Rendimiento quántico</s0>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE">
<s0>Luminance</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG">
<s0>Luminance</s0>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA">
<s0>Luminancia</s0>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE">
<s0>Luminescence</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG">
<s0>Luminescence</s0>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA">
<s0>Luminiscencia</s0>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="3" l="FRE">
<s0>Diode électroluminescente organique</s0>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="3" l="ENG">
<s0>Organic light emitting diodes</s0>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE">
<s0>Lumière bleue</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG">
<s0>Blue light</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA">
<s0>Luz azul</s0>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE">
<s0>Dérivé de l'anthracène</s0>
<s5>22</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG">
<s0>Anthracene derivatives</s0>
<s5>22</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA">
<s0>Antraceno derivado</s0>
<s5>22</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE">
<s0>Oxyde d'indium</s0>
<s5>23</s5>
</fC03>
<fC03 i1="12" i2="X" l="ENG">
<s0>Indium oxide</s0>
<s5>23</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA">
<s0>Indio óxido</s0>
<s5>23</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE">
<s0>Oxyde d'étain</s0>
<s5>24</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG">
<s0>Tin oxide</s0>
<s5>24</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA">
<s0>Estaño óxido</s0>
<s5>24</s5>
</fC03>
<fC03 i1="14" i2="3" l="FRE">
<s0>Amine aromatique polycyclique</s0>
<s5>25</s5>
</fC03>
<fC03 i1="14" i2="3" l="ENG">
<s0>Polycyclic aromatic amines</s0>
<s5>25</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE">
<s0>Anthracène</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>26</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG">
<s0>Anthracene</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>26</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA">
<s0>Antraceno</s0>
<s2>NK</s2>
<s2>FX</s2>
<s5>26</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE">
<s0>Quinoléin-8-ol</s0>
<s2>NK</s2>
<s2>FR</s2>
<s2>FF</s2>
<s5>27</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE">
<s0>Complexe d'aluminium</s0>
<s5>28</s5>
</fC03>
<fC03 i1="17" i2="X" l="ENG">
<s0>Aluminium complex</s0>
<s5>28</s5>
</fC03>
<fC03 i1="17" i2="X" l="SPA">
<s0>Aluminio complejo</s0>
<s5>28</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE">
<s0>Fluorure de lithium</s0>
<s5>29</s5>
</fC03>
<fC03 i1="18" i2="X" l="ENG">
<s0>Lithium fluoride</s0>
<s5>29</s5>
</fC03>
<fC03 i1="18" i2="X" l="SPA">
<s0>Litio fluoruro</s0>
<s5>29</s5>
</fC03>
<fC03 i1="19" i2="X" l="FRE">
<s0>Dispositif optoélectronique</s0>
<s5>31</s5>
</fC03>
<fC03 i1="19" i2="X" l="ENG">
<s0>Optoelectronic device</s0>
<s5>31</s5>
</fC03>
<fC03 i1="19" i2="X" l="SPA">
<s0>Dispositivo optoelectrónico</s0>
<s5>31</s5>
</fC03>
<fC03 i1="20" i2="X" l="FRE">
<s0>Electronique organique</s0>
<s5>32</s5>
</fC03>
<fC03 i1="20" i2="X" l="ENG">
<s0>Organic electronics</s0>
<s5>32</s5>
</fC03>
<fC03 i1="20" i2="X" l="SPA">
<s0>Electrónica orgánica</s0>
<s5>32</s5>
</fC03>
<fC03 i1="21" i2="X" l="FRE">
<s0>ITO</s0>
<s4>INC</s4>
<s5>82</s5>
</fC03>
<fC03 i1="22" i2="X" l="FRE">
<s0>LiF</s0>
<s4>INC</s4>
<s5>83</s5>
</fC03>
<fN21>
<s1>257</s1>
</fN21>
<fN44 i1="01">
<s1>OTO</s1>
</fN44>
<fN82>
<s1>OTO</s1>
</fN82>
</pA>
</standard>
</inist>
</record>

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