Two-dimensional π-conjugated molecules based-on 2,6,9,10-tetra(prop-1- yn-1-yl)anthracene and their application to solution-processed photovoltaic cells

Jicheol Shin; Nam Su Kang; Tae Wan Lee; Min Ju Cho; Jae Min Hong; Byeong Kwon Ju; Dong Hoon Choi

doi:10.1016/j.orgel.2014.04.021

Two-dimensional π-conjugated molecules based-on 2,6,9,10-tetra(prop-1- yn-1-yl)anthracene and their application to solution-processed photovoltaic cells

Jicheol Shin, Nam Su Kang, Tae Wan Lee, Min Ju Cho, Jae Min Hong, Byeong Kwon Ju, Dong Hoon Choi

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

11 Citations (Scopus)

Abstract

Novel two-dimensional π-conjugated molecules, i.e., 5′, 5″′-((9,10-bis((4-hexylphenyl)ethynyl)anthracene-2,6-diyl) bis(ethyne-2,1-diyl))bis(5-hexyl-2,2′-bithiophene) (2,6-HBT) and 5′,5″′-((2,6-bis((4-hexylphenyl)ethynyl)anthracene-9,10-diyl) bis(ethyne-2,1-diyl))bis(5-hexyl-2,2′-bithiophene) (9,10-THB) were successfully synthesized and utilized as highly soluble p-type organic semiconductors for organic thin film transistors (TFTs) and solar cells. From the TFTs, the high hole mobility of the pristine film of 9,10-THB was measured to be 0.07 cm² V^-1 s^-1 (I_on/off = 10⁶-10⁷), which is mainly attributed to slip-stacked charge-transport behavior in J-aggregation-induced crystallites. Further, a solution-processed solar cell made of 9,10-THB and PC₆₁BM exhibited very promising and reproducible power conversion efficiencies of 3.30% and 2.53% with composition 1:1 and 1:2 w/w ratio, respectively.

Original language	English
Pages (from-to)	1521-1530
Number of pages	10
Journal	Organic Electronics
Volume	15
Issue number	7
DOIs	https://doi.org/10.1016/j.orgel.2014.04.021
Publication status	Published - 2014 Jul

Bibliographical note

Funding Information:
This research was supported by National Research Foundation of Korea ( NRF2012R1A2A1A01008797 ) and by Key Research Institute Program through the NRF funded by the Ministry of Education, Science and Technology ( NRF20120005860 ). We are grateful to Pohang Accelerator Laboratory (Pohang, Korea) for allowing us to conduct the GI-XRD measurements.

Keywords

Bulk heterojunction
Organic semiconductor
Photovoltaic cell
Substitution position
Tetra(prop-1-yn-1-yl)anthracene
Thin film transistor

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Biomaterials
Chemistry(all)
Condensed Matter Physics
Materials Chemistry
Electrical and Electronic Engineering

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.orgel.2014.04.021

Cite this

@article{a7d4aecac2f94e1faa7830d046636531,

title = "Two-dimensional π-conjugated molecules based-on 2,6,9,10-tetra(prop-1- yn-1-yl)anthracene and their application to solution-processed photovoltaic cells",

abstract = "Novel two-dimensional π-conjugated molecules, i.e., 5′, 5″′-((9,10-bis((4-hexylphenyl)ethynyl)anthracene-2,6-diyl) bis(ethyne-2,1-diyl))bis(5-hexyl-2,2′-bithiophene) (2,6-HBT) and 5′,5″′-((2,6-bis((4-hexylphenyl)ethynyl)anthracene-9,10-diyl) bis(ethyne-2,1-diyl))bis(5-hexyl-2,2′-bithiophene) (9,10-THB) were successfully synthesized and utilized as highly soluble p-type organic semiconductors for organic thin film transistors (TFTs) and solar cells. From the TFTs, the high hole mobility of the pristine film of 9,10-THB was measured to be 0.07 cm2 V-1 s-1 (Ion/off = 106-107), which is mainly attributed to slip-stacked charge-transport behavior in J-aggregation-induced crystallites. Further, a solution-processed solar cell made of 9,10-THB and PC61BM exhibited very promising and reproducible power conversion efficiencies of 3.30% and 2.53% with composition 1:1 and 1:2 w/w ratio, respectively.",

keywords = "Bulk heterojunction, Organic semiconductor, Photovoltaic cell, Substitution position, Tetra(prop-1-yn-1-yl)anthracene, Thin film transistor",

author = "Jicheol Shin and Kang, {Nam Su} and Lee, {Tae Wan} and Cho, {Min Ju} and Hong, {Jae Min} and Ju, {Byeong Kwon} and Choi, {Dong Hoon}",

note = "Funding Information: This research was supported by National Research Foundation of Korea ( NRF2012R1A2A1A01008797 ) and by Key Research Institute Program through the NRF funded by the Ministry of Education, Science and Technology ( NRF20120005860 ). We are grateful to Pohang Accelerator Laboratory (Pohang, Korea) for allowing us to conduct the GI-XRD measurements.",

year = "2014",

month = jul,

doi = "10.1016/j.orgel.2014.04.021",

language = "English",

volume = "15",

pages = "1521--1530",

journal = "Organic Electronics",

issn = "1566-1199",

publisher = "Elsevier",

number = "7",

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TY - JOUR

T1 - Two-dimensional π-conjugated molecules based-on 2,6,9,10-tetra(prop-1- yn-1-yl)anthracene and their application to solution-processed photovoltaic cells

AU - Shin, Jicheol

AU - Kang, Nam Su

AU - Lee, Tae Wan

AU - Cho, Min Ju

AU - Hong, Jae Min

AU - Ju, Byeong Kwon

AU - Choi, Dong Hoon

N1 - Funding Information: This research was supported by National Research Foundation of Korea ( NRF2012R1A2A1A01008797 ) and by Key Research Institute Program through the NRF funded by the Ministry of Education, Science and Technology ( NRF20120005860 ). We are grateful to Pohang Accelerator Laboratory (Pohang, Korea) for allowing us to conduct the GI-XRD measurements.

PY - 2014/7

Y1 - 2014/7

N2 - Novel two-dimensional π-conjugated molecules, i.e., 5′, 5″′-((9,10-bis((4-hexylphenyl)ethynyl)anthracene-2,6-diyl) bis(ethyne-2,1-diyl))bis(5-hexyl-2,2′-bithiophene) (2,6-HBT) and 5′,5″′-((2,6-bis((4-hexylphenyl)ethynyl)anthracene-9,10-diyl) bis(ethyne-2,1-diyl))bis(5-hexyl-2,2′-bithiophene) (9,10-THB) were successfully synthesized and utilized as highly soluble p-type organic semiconductors for organic thin film transistors (TFTs) and solar cells. From the TFTs, the high hole mobility of the pristine film of 9,10-THB was measured to be 0.07 cm2 V-1 s-1 (Ion/off = 106-107), which is mainly attributed to slip-stacked charge-transport behavior in J-aggregation-induced crystallites. Further, a solution-processed solar cell made of 9,10-THB and PC61BM exhibited very promising and reproducible power conversion efficiencies of 3.30% and 2.53% with composition 1:1 and 1:2 w/w ratio, respectively.

AB - Novel two-dimensional π-conjugated molecules, i.e., 5′, 5″′-((9,10-bis((4-hexylphenyl)ethynyl)anthracene-2,6-diyl) bis(ethyne-2,1-diyl))bis(5-hexyl-2,2′-bithiophene) (2,6-HBT) and 5′,5″′-((2,6-bis((4-hexylphenyl)ethynyl)anthracene-9,10-diyl) bis(ethyne-2,1-diyl))bis(5-hexyl-2,2′-bithiophene) (9,10-THB) were successfully synthesized and utilized as highly soluble p-type organic semiconductors for organic thin film transistors (TFTs) and solar cells. From the TFTs, the high hole mobility of the pristine film of 9,10-THB was measured to be 0.07 cm2 V-1 s-1 (Ion/off = 106-107), which is mainly attributed to slip-stacked charge-transport behavior in J-aggregation-induced crystallites. Further, a solution-processed solar cell made of 9,10-THB and PC61BM exhibited very promising and reproducible power conversion efficiencies of 3.30% and 2.53% with composition 1:1 and 1:2 w/w ratio, respectively.

KW - Bulk heterojunction

KW - Organic semiconductor

KW - Photovoltaic cell

KW - Substitution position

KW - Tetra(prop-1-yn-1-yl)anthracene

KW - Thin film transistor

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DO - 10.1016/j.orgel.2014.04.021

M3 - Article

AN - SCOPUS:84900028112

SN - 1566-1199

VL - 15

SP - 1521

EP - 1530

JO - Organic Electronics

JF - Organic Electronics

IS - 7

ER -

Two-dimensional π-conjugated molecules based-on 2,6,9,10-tetra(prop-1- yn-1-yl)anthracene and their application to solution-processed photovoltaic cells

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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