Effect of fluorine substitution on naphtho[2,1-b:3,4-b′]bis[1]-benzothiophene-derived semiconductors for transistor application

Zhaoguang Li; Ji Zhang; Weifeng Zhang; Lei Guo; Jianyao Huang; Gui Yu; Man Shing Wong

doi:10.1016/j.orgel.2016.02.008

Effect of fluorine substitution on naphtho[2,1-b:3,4-b′]bis[1]-benzothiophene-derived semiconductors for transistor application

Zhaoguang Li, Ji Zhang, Weifeng Zhang, Lei Guo, Jianyao Huang, Gui Yu^*, Man Shing Wong

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

4 Citations (Scopus)

Abstract

A novel series of air-stable, fluorinated naphtho [2,1-b:3,4-b′]bis [1]-benzothiophenes bearing various lateral alkoxy-substituents, NBBTF-n (n = 8, 10, and 12) and its unsubstituted analogue, NBBT-10 were synthesized and investigated with field-effect transistor properties. Fluorine substitution affords desirable properties including high melting transition, high thermal stability and low-lying highest occupied molecular orbital (HOMO) energy levels for air-stable semiconductors. The OFET devices based on annealed NBBTF-10 films exhibit superior hole transport with mobility up to 0.35 cm² V^-1 s^-1 to that of NBBT-10, attributed to the close molecular stacking induced by fluorine substitution.

Original language	English
Pages (from-to)	47-53
Number of pages	7
Journal	Organic Electronics
Volume	32
DOIs	https://doi.org/10.1016/j.orgel.2016.02.008
Publication status	Published - 1 May 2016

User-Defined Keywords

Fluorine substitution
Hole mobility
Organic field-effect transistor
Organic semiconductor
Thienoacene

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10.1016/j.orgel.2016.02.008

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title = "Effect of fluorine substitution on naphtho[2,1-b:3,4-b′]bis[1]-benzothiophene-derived semiconductors for transistor application",

abstract = "A novel series of air-stable, fluorinated naphtho [2,1-b:3,4-b′]bis [1]-benzothiophenes bearing various lateral alkoxy-substituents, NBBTF-n (n = 8, 10, and 12) and its unsubstituted analogue, NBBT-10 were synthesized and investigated with field-effect transistor properties. Fluorine substitution affords desirable properties including high melting transition, high thermal stability and low-lying highest occupied molecular orbital (HOMO) energy levels for air-stable semiconductors. The OFET devices based on annealed NBBTF-10 films exhibit superior hole transport with mobility up to 0.35 cm2 V-1 s-1 to that of NBBT-10, attributed to the close molecular stacking induced by fluorine substitution.",

keywords = "Fluorine substitution, Hole mobility, Organic field-effect transistor, Organic semiconductor, Thienoacene",

author = "Zhaoguang Li and Ji Zhang and Weifeng Zhang and Lei Guo and Jianyao Huang and Gui Yu and Wong, {Man Shing}",

note = "Funding Information: This work was supported by GRF ( HKBU 203212 ) and Theme-Based Research Scheme (project no. [ T23-713/11 ]), Hong Kong Research Grant Council and Institute of Molecular Functional Materials which was supported by a grant from the University Grants Committee , Areas of Excellence Scheme ( AoE/P-03/08 ). This research was also financially supported by the National Science Foundation of China ( 21021091 ), the Major State Basic Research Development Program ( 2011CB808403 ), and the Chinese Academy of Sciences . ",

year = "2016",

month = may,

day = "1",

doi = "10.1016/j.orgel.2016.02.008",

language = "English",

volume = "32",

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journal = "Organic Electronics",

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TY - JOUR

T1 - Effect of fluorine substitution on naphtho[2,1-b:3,4-b′]bis[1]-benzothiophene-derived semiconductors for transistor application

AU - Li, Zhaoguang

AU - Zhang, Ji

AU - Zhang, Weifeng

AU - Guo, Lei

AU - Huang, Jianyao

AU - Yu, Gui

AU - Wong, Man Shing

N1 - Funding Information: This work was supported by GRF ( HKBU 203212 ) and Theme-Based Research Scheme (project no. [ T23-713/11 ]), Hong Kong Research Grant Council and Institute of Molecular Functional Materials which was supported by a grant from the University Grants Committee , Areas of Excellence Scheme ( AoE/P-03/08 ). This research was also financially supported by the National Science Foundation of China ( 21021091 ), the Major State Basic Research Development Program ( 2011CB808403 ), and the Chinese Academy of Sciences .

PY - 2016/5/1

Y1 - 2016/5/1

N2 - A novel series of air-stable, fluorinated naphtho [2,1-b:3,4-b′]bis [1]-benzothiophenes bearing various lateral alkoxy-substituents, NBBTF-n (n = 8, 10, and 12) and its unsubstituted analogue, NBBT-10 were synthesized and investigated with field-effect transistor properties. Fluorine substitution affords desirable properties including high melting transition, high thermal stability and low-lying highest occupied molecular orbital (HOMO) energy levels for air-stable semiconductors. The OFET devices based on annealed NBBTF-10 films exhibit superior hole transport with mobility up to 0.35 cm2 V-1 s-1 to that of NBBT-10, attributed to the close molecular stacking induced by fluorine substitution.

AB - A novel series of air-stable, fluorinated naphtho [2,1-b:3,4-b′]bis [1]-benzothiophenes bearing various lateral alkoxy-substituents, NBBTF-n (n = 8, 10, and 12) and its unsubstituted analogue, NBBT-10 were synthesized and investigated with field-effect transistor properties. Fluorine substitution affords desirable properties including high melting transition, high thermal stability and low-lying highest occupied molecular orbital (HOMO) energy levels for air-stable semiconductors. The OFET devices based on annealed NBBTF-10 films exhibit superior hole transport with mobility up to 0.35 cm2 V-1 s-1 to that of NBBT-10, attributed to the close molecular stacking induced by fluorine substitution.

KW - Fluorine substitution

KW - Hole mobility

KW - Organic field-effect transistor

KW - Organic semiconductor

KW - Thienoacene

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DO - 10.1016/j.orgel.2016.02.008

M3 - Journal article

AN - SCOPUS:84958761534

SN - 1566-1199

VL - 32

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EP - 53

JO - Organic Electronics

JF - Organic Electronics

ER -

Effect of fluorine substitution on naphtho[2,1-b:3,4-b′]bis[1]-benzothiophene-derived semiconductors for transistor application

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