Stilbene like carbazole dimer-based electroluminescent materials

Chih Hsin Chen; Jiann T. Lin; Ming Chang P. Yeh

doi:10.1016/j.tet.2006.06.067

Stilbene like carbazole dimer-based electroluminescent materials

Chih Hsin Chen, Jiann T. Lin^*, Ming Chang P. Yeh

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

20 Citations (Scopus)

Abstract

Two carbazole dimers (1 and 10) were synthesized from 9-ethyl-9H-carbazole-3-carbaldehyde and 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde by McMurry C-C coupling reaction. Palladium(0)-catalyzed C-N coupling reactions of 10 and various diarylamines result in the formation of stable carbazole derivatives in good yields. These compounds are fluorescent in blue to yellow region with moderate to good quantum yields. Also, they are thermally stable and capable of hole-transporting due to the presence of the carbazole moieties. The electroluminescent devices fabricated using 1, 2, and 3 as hole-transporters/emitters with a bilayer structure ITO/Cpd/TPBI or Alq₃/LiF/Al (Cpd=1, 2, and 3) exhibit good performance (e.g., η_ext=1.0-2.1%; η_p=0.9-1.9 lm/W; η_c=2.4-4.8 cd/A at a current density of 100 mA/cm²).

Original language	English
Pages (from-to)	8564-8570
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	36
DOIs	https://doi.org/10.1016/j.tet.2006.06.067
Publication status	Published - 2006 Sept 4

Keywords

Carbazole dimmer
Electroluminescent
McMurry C-C coupling reaction

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2006.06.067

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@article{8ed5a6a430004f6e92577e35febd8942,

title = "Stilbene like carbazole dimer-based electroluminescent materials",

abstract = "Two carbazole dimers (1 and 10) were synthesized from 9-ethyl-9H-carbazole-3-carbaldehyde and 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde by McMurry C-C coupling reaction. Palladium(0)-catalyzed C-N coupling reactions of 10 and various diarylamines result in the formation of stable carbazole derivatives in good yields. These compounds are fluorescent in blue to yellow region with moderate to good quantum yields. Also, they are thermally stable and capable of hole-transporting due to the presence of the carbazole moieties. The electroluminescent devices fabricated using 1, 2, and 3 as hole-transporters/emitters with a bilayer structure ITO/Cpd/TPBI or Alq3/LiF/Al (Cpd=1, 2, and 3) exhibit good performance (e.g., ηext=1.0-2.1%; ηp=0.9-1.9 lm/W; ηc=2.4-4.8 cd/A at a current density of 100 mA/cm2).",

keywords = "Carbazole dimmer, Electroluminescent, McMurry C-C coupling reaction",

author = "Chen, {Chih Hsin} and Lin, {Jiann T.} and Yeh, {Ming Chang P.}",

note = "Funding Information: We are thankful to Academia Sinica, National Taiwan Normal University, and National Science Council for financial support. ",

year = "2006",

month = sep,

day = "4",

doi = "10.1016/j.tet.2006.06.067",

language = "English",

volume = "62",

pages = "8564--8570",

journal = "Tetrahedron",

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TY - JOUR

T1 - Stilbene like carbazole dimer-based electroluminescent materials

AU - Chen, Chih Hsin

AU - Lin, Jiann T.

AU - Yeh, Ming Chang P.

N1 - Funding Information: We are thankful to Academia Sinica, National Taiwan Normal University, and National Science Council for financial support.

PY - 2006/9/4

Y1 - 2006/9/4

N2 - Two carbazole dimers (1 and 10) were synthesized from 9-ethyl-9H-carbazole-3-carbaldehyde and 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde by McMurry C-C coupling reaction. Palladium(0)-catalyzed C-N coupling reactions of 10 and various diarylamines result in the formation of stable carbazole derivatives in good yields. These compounds are fluorescent in blue to yellow region with moderate to good quantum yields. Also, they are thermally stable and capable of hole-transporting due to the presence of the carbazole moieties. The electroluminescent devices fabricated using 1, 2, and 3 as hole-transporters/emitters with a bilayer structure ITO/Cpd/TPBI or Alq3/LiF/Al (Cpd=1, 2, and 3) exhibit good performance (e.g., ηext=1.0-2.1%; ηp=0.9-1.9 lm/W; ηc=2.4-4.8 cd/A at a current density of 100 mA/cm2).

AB - Two carbazole dimers (1 and 10) were synthesized from 9-ethyl-9H-carbazole-3-carbaldehyde and 6-bromo-9-ethyl-9H-carbazole-3-carbaldehyde by McMurry C-C coupling reaction. Palladium(0)-catalyzed C-N coupling reactions of 10 and various diarylamines result in the formation of stable carbazole derivatives in good yields. These compounds are fluorescent in blue to yellow region with moderate to good quantum yields. Also, they are thermally stable and capable of hole-transporting due to the presence of the carbazole moieties. The electroluminescent devices fabricated using 1, 2, and 3 as hole-transporters/emitters with a bilayer structure ITO/Cpd/TPBI or Alq3/LiF/Al (Cpd=1, 2, and 3) exhibit good performance (e.g., ηext=1.0-2.1%; ηp=0.9-1.9 lm/W; ηc=2.4-4.8 cd/A at a current density of 100 mA/cm2).

KW - Carbazole dimmer

KW - Electroluminescent

KW - McMurry C-C coupling reaction

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EP - 8570

JO - Tetrahedron

JF - Tetrahedron

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ER -

Stilbene like carbazole dimer-based electroluminescent materials

Abstract

Keywords

ASJC Scopus subject areas

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