Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells

Jae Hoon Yun, Sungmin Park, Jin Hyuck Heo, Hyo Sang Lee, Seongwon Yoon, Jinback Kang, Sang Hyuk Im, Hyunjung Kim, Wonmok Lee, Bongsoo Kim, Min Jae Ko, Dae Sung Chung, Hae Jung Son

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

We prepared a series of small molecules based on 7,7′-(4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl)bis(4-(5′-hexyl-[2,2′-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole) with different fluorine substitution patterns (0F-4F). Depending on symmetricity and numbers of fluorine atoms incorporated in the benzo[c][1,2,5]thiadiazole unit, they show very different optical and morphological properties in a film. 2F and 4F, which featured symmetric and even-numbered fluorine substitution patterns, display improved molecular packing structures and higher crystalline properties in a film compared with 1F and 3F and thus, 2F achieved the highest OTFT mobility, which is followed by 4F. In the bulk heterojunction solar cell fabricated with PC71BM, 2F achieves the highest photovoltaic performance with an 8.14% efficiency and 0F shows the lowest efficiency of 1.28%. Moreover, the planar-type perovskite solar cell (PSC) prepared with 2F as a dopant-free hole transport material shows a high power conversion efficiency of 14.5% due to its high charge transporting properties, which were significantly improved compared with the corresponding PSC device obtained from 0F (8.5%). From the studies, it is demonstrated that low variation in the local dipole moment and the narrow distribution of 2F conformers make intermolecular interactions favorable, which may effectively drive crystal formations in the solid state and thus, higher charge transport properties compared with 1F and 3F.

Original languageEnglish
Pages (from-to)6649-6661
Number of pages13
JournalChemical Science
Volume7
Issue number11
DOIs
Publication statusPublished - 2016 Jan 1
Externally publishedYes

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Fluorine
Thiadiazoles
Transport properties
Charge transfer
Substitution reactions
Semiconductor materials
Molecules
Dipole moment
Conversion efficiency
Heterojunctions
Solar cells
Display devices
Doping (additives)
Crystalline materials
Atoms
Crystals
Perovskite solar cells
Organic solar cells

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells. / Yun, Jae Hoon; Park, Sungmin; Heo, Jin Hyuck; Lee, Hyo Sang; Yoon, Seongwon; Kang, Jinback; Im, Sang Hyuk; Kim, Hyunjung; Lee, Wonmok; Kim, Bongsoo; Ko, Min Jae; Chung, Dae Sung; Son, Hae Jung.

In: Chemical Science, Vol. 7, No. 11, 01.01.2016, p. 6649-6661.

Research output: Contribution to journalArticle

Yun, Jae Hoon ; Park, Sungmin ; Heo, Jin Hyuck ; Lee, Hyo Sang ; Yoon, Seongwon ; Kang, Jinback ; Im, Sang Hyuk ; Kim, Hyunjung ; Lee, Wonmok ; Kim, Bongsoo ; Ko, Min Jae ; Chung, Dae Sung ; Son, Hae Jung. / Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells. In: Chemical Science. 2016 ; Vol. 7, No. 11. pp. 6649-6661.
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abstract = "We prepared a series of small molecules based on 7,7′-(4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl)bis(4-(5′-hexyl-[2,2′-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole) with different fluorine substitution patterns (0F-4F). Depending on symmetricity and numbers of fluorine atoms incorporated in the benzo[c][1,2,5]thiadiazole unit, they show very different optical and morphological properties in a film. 2F and 4F, which featured symmetric and even-numbered fluorine substitution patterns, display improved molecular packing structures and higher crystalline properties in a film compared with 1F and 3F and thus, 2F achieved the highest OTFT mobility, which is followed by 4F. In the bulk heterojunction solar cell fabricated with PC71BM, 2F achieves the highest photovoltaic performance with an 8.14{\%} efficiency and 0F shows the lowest efficiency of 1.28{\%}. Moreover, the planar-type perovskite solar cell (PSC) prepared with 2F as a dopant-free hole transport material shows a high power conversion efficiency of 14.5{\%} due to its high charge transporting properties, which were significantly improved compared with the corresponding PSC device obtained from 0F (8.5{\%}). From the studies, it is demonstrated that low variation in the local dipole moment and the narrow distribution of 2F conformers make intermolecular interactions favorable, which may effectively drive crystal formations in the solid state and thus, higher charge transport properties compared with 1F and 3F.",
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T1 - Enhancement of charge transport properties of small molecule semiconductors by controlling fluorine substitution and effects on photovoltaic properties of organic solar cells and perovskite solar cells

AU - Yun, Jae Hoon

AU - Park, Sungmin

AU - Heo, Jin Hyuck

AU - Lee, Hyo Sang

AU - Yoon, Seongwon

AU - Kang, Jinback

AU - Im, Sang Hyuk

AU - Kim, Hyunjung

AU - Lee, Wonmok

AU - Kim, Bongsoo

AU - Ko, Min Jae

AU - Chung, Dae Sung

AU - Son, Hae Jung

PY - 2016/1/1

Y1 - 2016/1/1

N2 - We prepared a series of small molecules based on 7,7′-(4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl)bis(4-(5′-hexyl-[2,2′-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole) with different fluorine substitution patterns (0F-4F). Depending on symmetricity and numbers of fluorine atoms incorporated in the benzo[c][1,2,5]thiadiazole unit, they show very different optical and morphological properties in a film. 2F and 4F, which featured symmetric and even-numbered fluorine substitution patterns, display improved molecular packing structures and higher crystalline properties in a film compared with 1F and 3F and thus, 2F achieved the highest OTFT mobility, which is followed by 4F. In the bulk heterojunction solar cell fabricated with PC71BM, 2F achieves the highest photovoltaic performance with an 8.14% efficiency and 0F shows the lowest efficiency of 1.28%. Moreover, the planar-type perovskite solar cell (PSC) prepared with 2F as a dopant-free hole transport material shows a high power conversion efficiency of 14.5% due to its high charge transporting properties, which were significantly improved compared with the corresponding PSC device obtained from 0F (8.5%). From the studies, it is demonstrated that low variation in the local dipole moment and the narrow distribution of 2F conformers make intermolecular interactions favorable, which may effectively drive crystal formations in the solid state and thus, higher charge transport properties compared with 1F and 3F.

AB - We prepared a series of small molecules based on 7,7′-(4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b′]dithiophene-2,6-diyl)bis(4-(5′-hexyl-[2,2′-bithiophene]-5-yl)benzo[c][1,2,5]thiadiazole) with different fluorine substitution patterns (0F-4F). Depending on symmetricity and numbers of fluorine atoms incorporated in the benzo[c][1,2,5]thiadiazole unit, they show very different optical and morphological properties in a film. 2F and 4F, which featured symmetric and even-numbered fluorine substitution patterns, display improved molecular packing structures and higher crystalline properties in a film compared with 1F and 3F and thus, 2F achieved the highest OTFT mobility, which is followed by 4F. In the bulk heterojunction solar cell fabricated with PC71BM, 2F achieves the highest photovoltaic performance with an 8.14% efficiency and 0F shows the lowest efficiency of 1.28%. Moreover, the planar-type perovskite solar cell (PSC) prepared with 2F as a dopant-free hole transport material shows a high power conversion efficiency of 14.5% due to its high charge transporting properties, which were significantly improved compared with the corresponding PSC device obtained from 0F (8.5%). From the studies, it is demonstrated that low variation in the local dipole moment and the narrow distribution of 2F conformers make intermolecular interactions favorable, which may effectively drive crystal formations in the solid state and thus, higher charge transport properties compared with 1F and 3F.

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