Structural and morphological tuning of dithienobenzodithiophene-core small molecules for efficient solution processed organic solar cells

Minwoo Jung, Dongkyun Seo, Kyungwon Kwak, Ajeong Kim, Wonsuk Cha, Hyunjung Kim, Youngwoon Yoon, Min Jae Ko, Doh Kwon Lee, Jin Young Kim, Hae Jung Son, Bong Soo Kim

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

The fused dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDT) structure was coupled with diketopyrrolopyrrole (DPP) moieties to generate highly planar bis(2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione)dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDTDPP-EH) and bis(2,5-bis(2-butyloctyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione)dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDTDPP-BO) molecules, where the EH and BO stands for 2-ethylhexyl and 2-butyloctyl groups respectively. The morphology of the DTBDTDPP-EH alone or DTBDTDPP-EH:[6,6]-phenyl-C61-butyric acid methyl ester (PCBM) blend film was controlled using post-thermal annealing at 130°C or addition of 1,8-diiodooctane (DIO) additives. The DIO-additive treatment was more effective than thermal annealing at increasing crystallinity; the DIO-additives promoted the formation of nanoscopically well-connected molecular crystalline domains in the blend films. This observation well explained the ordering of the photovoltaic properties of DTBDTDPP-EH:PCBM devices: from worst to best, as-cast, thermally treated, and DIO-treated photoactive films. The DTBDTDPP-BO:PCBM device followed the similar trend with lower performances due to the presence of irregularly overgrown domains. Overall, we demonstrate that it is critical to optimize nanoscale film morphologies by engineering alkyl chains and selecting an appropriate processing method.

Original languageEnglish
Pages (from-to)23-34
Number of pages12
JournalDyes and Pigments
Volume115
DOIs
Publication statusPublished - 2014 Dec 13
Externally publishedYes

Fingerprint

Butyric acid
Tuning
Esters
Pyrroles
Molecules
Butyric Acid
Annealing
Crystalline materials
Organic solar cells
Processing
Hot Temperature

Keywords

  • Conjugated small molecules
  • Crystallinity
  • Nanoscale phase separation
  • Organic semiconductors
  • Organic solar cells
  • Power conversion efficiency

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Process Chemistry and Technology

Cite this

Structural and morphological tuning of dithienobenzodithiophene-core small molecules for efficient solution processed organic solar cells. / Jung, Minwoo; Seo, Dongkyun; Kwak, Kyungwon; Kim, Ajeong; Cha, Wonsuk; Kim, Hyunjung; Yoon, Youngwoon; Ko, Min Jae; Lee, Doh Kwon; Kim, Jin Young; Son, Hae Jung; Kim, Bong Soo.

In: Dyes and Pigments, Vol. 115, 13.12.2014, p. 23-34.

Research output: Contribution to journalArticle

Jung, Minwoo ; Seo, Dongkyun ; Kwak, Kyungwon ; Kim, Ajeong ; Cha, Wonsuk ; Kim, Hyunjung ; Yoon, Youngwoon ; Ko, Min Jae ; Lee, Doh Kwon ; Kim, Jin Young ; Son, Hae Jung ; Kim, Bong Soo. / Structural and morphological tuning of dithienobenzodithiophene-core small molecules for efficient solution processed organic solar cells. In: Dyes and Pigments. 2014 ; Vol. 115. pp. 23-34.
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abstract = "The fused dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDT) structure was coupled with diketopyrrolopyrrole (DPP) moieties to generate highly planar bis(2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione)dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDTDPP-EH) and bis(2,5-bis(2-butyloctyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione)dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDTDPP-BO) molecules, where the EH and BO stands for 2-ethylhexyl and 2-butyloctyl groups respectively. The morphology of the DTBDTDPP-EH alone or DTBDTDPP-EH:[6,6]-phenyl-C61-butyric acid methyl ester (PCBM) blend film was controlled using post-thermal annealing at 130°C or addition of 1,8-diiodooctane (DIO) additives. The DIO-additive treatment was more effective than thermal annealing at increasing crystallinity; the DIO-additives promoted the formation of nanoscopically well-connected molecular crystalline domains in the blend films. This observation well explained the ordering of the photovoltaic properties of DTBDTDPP-EH:PCBM devices: from worst to best, as-cast, thermally treated, and DIO-treated photoactive films. The DTBDTDPP-BO:PCBM device followed the similar trend with lower performances due to the presence of irregularly overgrown domains. Overall, we demonstrate that it is critical to optimize nanoscale film morphologies by engineering alkyl chains and selecting an appropriate processing method.",
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AU - Jung, Minwoo

AU - Seo, Dongkyun

AU - Kwak, Kyungwon

AU - Kim, Ajeong

AU - Cha, Wonsuk

AU - Kim, Hyunjung

AU - Yoon, Youngwoon

AU - Ko, Min Jae

AU - Lee, Doh Kwon

AU - Kim, Jin Young

AU - Son, Hae Jung

AU - Kim, Bong Soo

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N2 - The fused dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDT) structure was coupled with diketopyrrolopyrrole (DPP) moieties to generate highly planar bis(2,5-bis(2-ethylhexyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione)dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDTDPP-EH) and bis(2,5-bis(2-butyloctyl)-3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione)dithieno[2,3-d:2′,3′-d′]benzo[1,2-b:4,5-b′]dithiophene (DTBDTDPP-BO) molecules, where the EH and BO stands for 2-ethylhexyl and 2-butyloctyl groups respectively. The morphology of the DTBDTDPP-EH alone or DTBDTDPP-EH:[6,6]-phenyl-C61-butyric acid methyl ester (PCBM) blend film was controlled using post-thermal annealing at 130°C or addition of 1,8-diiodooctane (DIO) additives. The DIO-additive treatment was more effective than thermal annealing at increasing crystallinity; the DIO-additives promoted the formation of nanoscopically well-connected molecular crystalline domains in the blend films. This observation well explained the ordering of the photovoltaic properties of DTBDTDPP-EH:PCBM devices: from worst to best, as-cast, thermally treated, and DIO-treated photoactive films. The DTBDTDPP-BO:PCBM device followed the similar trend with lower performances due to the presence of irregularly overgrown domains. Overall, we demonstrate that it is critical to optimize nanoscale film morphologies by engineering alkyl chains and selecting an appropriate processing method.

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KW - Organic semiconductors

KW - Organic solar cells

KW - Power conversion efficiency

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