New multi-phenylated carbazole derivatives for OLED through Diels-Alder reaction

Article abstract of DOI:10.1080/15421400701495674

We synthesized multi-phenylated carbazole derivatives such as 3,6-Bis[(2,3,4,5-tetraphenyl)phenyl]-9-ethylcarbazole(BTPEC) and 3,6-Bis(7,10-diphenyl-fluoranthene)-9-ethlycarbazole(BDPEC), through Diels-Alder reaction. These products were identified by NMR, Fab-Mass analysis. Electro-optical properties of these materials were characterized by cyclic voltammetry (CV) and, UV-visible and photoluminescence (PL) spectra. The maximum absorbance of BTPEC appeared at 307 nm and BDPEC showed maximum absorbance of 307 nm and 388 nm. And two compounds also exhibited PL peaks at 389 nm and 483 nm. When we used these two materials as hole injection layer(HIL) and hole transport layer(HTL) in OLED device, the devices showed about 3 cd/A and 2 cd/A, respectively.

Full text of DOI:10.1080/15421400701495674

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New Multi-Phenylated
Carbazole Derivatives for OLED
through Diels-Alder Reaction
Young-Il Park a , Seung-Eun Lee a , Jong-Wook Park a
& Se-Young Oh b
a Department of Chemistry/Display Research
Center , The Catholic University of Korea , Pucheon,
Korea
b Department of Chemical Engineering , Sogang
University , Mapo, Korea
Published online: 22 Sep 2010.
To cite this article: Young-Il Park , Seung-Eun Lee , Jong-Wook Park & Se-Young
Oh (2007) New Multi-Phenylated Carbazole Derivatives for OLED through Diels-
Alder Reaction, Molecular Crystals and Liquid Crystals, 470:1, 223-230, DOI:
10.1080/15421400701495674
To link to this article: http://dx.doi.org/10.1080/15421400701495674
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Mol. Cryst. Liq. Cryst., Vol. 470, pp. 223–230, 2007
Copyright # Taylor & Francis Group, LLC
ISSN: 1542-1406 print=1563-5287 online
DOI: 10.1080/15421400701495674
New Multi-Phenylated Carbazole Derivatives for OLED
through Diels-Alder Reaction
Young-Il Park
Seung-Eun Lee
Jong-Wook Park
Department of Chemistry=Display Research Center, The Catholic
University of Korea, Pucheon, Korea
Se-Young Oh
Department of Chemical Engineering, Sogang University,
Mapo, Korea
We synthesized multi-phenylated carbazole derivatives such as 3,6-Bis[(2,3,4,5-tetra-
phenyl)phenyl]-9-ethylcarbazole(BTPEC) and 3,6-Bis(7,10-diphenyl-fluoranthene)-9-
ethlycarbazole(BDPEC), through Diels-Alder reaction. These products were identified
by NMR, Fab-Mass analysis.
Electro-optical properties of these materials were characterized by cyclic voltam-
metry (CV) and, UV-visible and photoluminescence (PL) spectra. The maximum
absorbance of BTPEC appeared at 307 nm and BDPEC showed maximum absor-
bance of 307 nm and 388 nm. And two compounds also exhibited PL peaks at
389 nm and 483 nm. When we used these two materials as hole injection layer(HIL)
and hole transport layer(HTL) in OLED device, the devices showed about 3 cd=A
and 2 cd=A, respectively.
Keywords: Diels-Alder reaction; electroluminescent; hole injection; hole transport;
organic light-emitting diode
This work was supported by grant No. R01-2006-00010196 from the Basic Research
Program of the Korea Science & Engineering Foundation.
This study was supported by the department specialization Fund, 2007 of The
Catholic University of Korea.
Address correspondence to Jong-Wook Park, Department of Chemistry=Display
Research Center, The Catholic University of Korea, Pucheon 420-743, Korea. E-mail:
hahapark@catholic.ac.kr
223

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224
Y.-I. Park et al.
INTRODUCTION
Organic light-emitting diodes (OLEDs) based on organic molecules are
currently the subject of an intense research effort due to their promise
as devices for full-color large display applications [1–2]. Recently, a
star-burst amine 4,40,400-tris{N,(3-methylphenyl)-N-phenylamino}-
triphenylamine(m-MTDATA)[3], 4,40,400-tris{N,-(2-naphthyl)-N-pheny-
lamino}-triphenylamine (2-TNATA) [3] and copper phthalocyanine
(CuPc) [4] compounds acting as a hole injection layer(HIL) in OLED
device, have been inserted between hole transporting layer(HTL)
and the transparent anode such as ITO in order to improve device
performance.
Unfortunately, CuPc absorbs slightly blue and red light and
m-MTDATA has disadvantage of low Tg as 75ꢀC [5,6]. This issues
make kind of limitation to apply materials to device.
Our group have firstly synthesized several kinds of multipheny-
lated compound by using Diels-Alder reaction [7,8]. Recently,
Gelsen et al. reported multiphenylated compounds as a HTL in OLED
device [9].
In this study, we synthesized 3,6-Bis[(2,3,4,5-tetraphenyl)phenyl]-
9-ethylcarbazole(BTPEC) and 3,6-Bis(7,10-diphenyl-fluoranthene)-9-
ethlycarbazole(BDPEC), as multi-phenylated carbazole derivatives
by using Diels-Alder reaction. Electro-optical properties of these mate-
rials were characterized by cyclic voltammetry(CV) and, UV-visible
and photoluminescence (PL) spectra. Multilayered EL devices were
fabricated using these materials as a hole injection layer (HIL), hole
transport layer (HTL).
EXPERIMENTAL
Synthesis
3,6-Bis[(2,3,4,5-tetraphenyl)phenyl]-9-ethylcarbazole(BTPEC)
9-ethyl-3,6-diethnyl-9H-carbazole(1 g, 4.1 mmol) and 2,3,4,5-tetra-
phenyl cyclopenta-2,4-dienone(3.47 g, 9.04 mmol) were added to dried
xylene solvent (100 ml). This mixture was heated to 120ꢀC for 12 hr
until no ejecting CO gas. After the reaction mixture cooled, the
solution was evaporated. The residue was dissolved in CHCl3 and
ethanol. And the residue was purified by column chromatography
with EA: n-Hexane(1:10) eluent to afford white solid(1.13 g, 28%)
(Scheme 1).
1H NMR(CDCl3) d: 7.89 (s, 2H), 7.67 (s, 2H), 7.17–6.80(m, 44H),
4.21(q, 2H), 1.34(t, 3H)=Fabþ -Mass m=e: 956