Progress in the Application of Fluorine-Substituted Organic Hole Transport Materials for Perovskite Solar Cells

doi:10.6023/cjoc202307008

Abstract

Perovskite solar cells (PSCs) are of significant importance in the fields of environment, ecology, and energy structure adjustment due to their exceptional performance, cost-effectiveness, and straightforward preparation process. Among them, hole transport materials (HTMs) play a crucial role in PSCs by effectively regulating the battery interface barrier, facilitating hole transport and collection, reducing charge recombination, optimizing the perovskite layer-electrode interface, and enhancing the properties of perovskite light absorption layer. Fluorine-substituted materials possess unique charge transport and photoelectric properties. The introduction of fluorine atoms into organic molecules through induction and conjugation effects can lower molecular energy levels, improve HTM hole mobility thereby enhancing PSCs performance. This paper provides a comprehensive review and summary on the impact of fluorine-substituted organic hole transport materials on the photoelectric properties of PSCs as well as their underlying mechanisms.

Key words: perovskite solar cells, hole transport material, fluorine substitution, organic material

Cite this article

Dong Liu, Xiaoye Zhang, Zhanfeng Li. Progress in the Application of Fluorine-Substituted Organic Hole Transport Materials for Perovskite Solar Cells[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1197-1209.

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HTM	Device configuration	J_sc/(mA•cm^-2)	V_oc/V	FF/%	PCE/%	Ref.
n-i-p devices
SFX-p-2F	FTO/SnO₂/Cs_0.05(MA_0.13FA_0.87)_0.95Pb(I_0.83Br_0.17)₃/HTM/Au	22.23	1.14	61.46	16.33	[57]
SFX-m-2F	FTO/SnO₂/Cs_0.05(MA_0.13FA_0.87)_0.95Pb(I_0.83Br_0.17)₃/HTM/Au	22.64	1.16	71.85	18.86	[57]
B3	FTO/TiO₂/m-TiO₂/CH₃NH₃PbI₃/HTM/Au	20.90	0.91	64.00	12.10	[62]
CzPF	FTO/c-TiO₂/PCBM/MAPbI₃/HTM/Au	17.31	1.03	70.00	12.41	[60]
TPB-2F	FTO/c-TiO₂/MAPbI₃/HTM/Au	18.66	1.01	74.00	13.96	[54]
BDT2FMeDPA	FTO/c-TiO₂/mp-TiO₂/(FAPbI₃)_0.85 (MAPbBr₃)_0.15/HTM/carbon	21.40	1.00	66.00	14.50	[20]
SF-DTBT	FTO/bl-TiO₂/mp-TiO_2/MAPbI₃/HTM/Au	22.80	0.97	70.00	15.50	[55]
DF-DTBT	FTO/bl-TiO₂/mp-TiO_2/MAPbI₃/HTM/Au	22.82	1.10	74.00	18.70	[55]
JY7	FTO/c-TiO₂/CH₃NH₃PbI_3-_xCl_x/HTM/Ag	20.58	1.05	73.00	15.71	[58]
JY6	FTO/c-TiO₂/CH₃NH₃PbI_3-_xCl_x/HTM/Ag	21.39	1.07	81.00	18.54	[58]
FOMePh	FTO/bl-TiO₂/mp-TiO₂/(FAPbI₃)_0.85(MAPbBr₃)_0.15/HTM/Au	23.95	0.98	72.53	17.08	[56]
DFBT(DTS-FBTTh₂)₂	FTO/TiO₂/MAPbI₃/HTM/Au	20.70	1.10	76.00	17.30	[52]
2FBTA-2	FTO/c-TiO₂/m-TiO₂/FA_1-_xMA_xPbI₃/HTM/Au	21.53	1.06	78.62	17.94	[61]
IDIDF	FTO/bl-TiO₂/mp-TiO₂/(FAPbI₃)_0.92(MAPbBr₃)_0.08/HTM/Au	23.55	1.04	77.20	19.05	[65]
p-DTS(FBTTh₂)₂	FTO/TiO₂/MAPbI₃/HTM/Au	20.60	1.10	79.40	18.00	[53]
CB-2	FTO/c-TiO₂/mp-TiO₂/SnO₂/[(FAPbI₃)_0.87(MAPbBr₃)_0.13]_0.92-(CsPbI₃)_0.08]/HTM/Au	23.19	1.02	76.70	18.23	[64]
tpa-t-FBTD	FTO/SnO₂/(FAPbI₃)_0.85(MAPbBr₃)_0.15/HTM/Au	22.40	1.08	78.10	18.90	[59]
3,6-SFY	FTO/c-TiO₂/mp-TiO₂/FAPbI₃/HTM/Au	23.17	1.08	76.00	19.02	[63]
2,7-SFY	FTO/c-TiO₂/mp-TiO₂/FAPbI₃/HTM/Au	23.73	1.08	80.00	20.29	[63]
Spiro-oF	FTO/c-TiO₂/mp-TiO₂/FAPbI₃/HTM/Au	26.34	1.16	80.15	24.50	[51]
Spiro-mF	FTO/c-TiO₂/mp-TiO₂/FAPbI₃/HTM/Au	26.35	1.16	80.90	24.82	[51]
p-i-n devices
D43	ITO/HTM/CH₃NH₃PbI₃/PC₆₁BM/BCP/Ag	17.67	1.00	68.40	12.13	[68]
DFTAB	ITO/HTM/CH₃NH₃PbI₃/PCBM/Ag	17.50	1.07	69.00	12.40	[72]
3-F-br-4C	ITO/HTM/MAPbI₃/C₆₀/BCP/Ag	20.20	1.06	80.00	17.20	[67]
H2	ITO/HTM/CH₃NH₃PbI₃/PCBM/BCP/Ag	22.93	1.06	76.90	18.69	[19]
INIC-1F	ITO/PEDOT:PSS/MAPbI_3-_xCl_x/HTM/PCBM/PDIN/Ag	22.80	1.01	81.50	18.80	[70]
INIC-2F	ITO/PEDOT:PSS/MAPbI_3-_xCl_x/HTM/PCBM/PDIN/Ag	23.10	1.01	82.70	19.30	[70]
n-i-p devices
DFBT-MTP	ITO/HTM/MAPbI_3-_xCl_x/C₆₀/BCP/Ag	23.01	1.10	79.70	20.15	[71]
HTM-F	ITO/HTM/(FAPbI₃)_1-_x(MAPbBr₃)_x/C₆₀/BCP/Ag	23.03	1.09	82.00	20.51	[69]

HTM	Device configuration	J_sc/(mA•cm^-2)	V_oc/V	FF/%	PCE/%	Ref.
n-i-p devices
SFX-p-2F	FTO/SnO₂/Cs_0.05(MA_0.13FA_0.87)_0.95Pb(I_0.83Br_0.17)₃/HTM/Au	22.23	1.14	61.46	16.33	[57]
SFX-m-2F	FTO/SnO₂/Cs_0.05(MA_0.13FA_0.87)_0.95Pb(I_0.83Br_0.17)₃/HTM/Au	22.64	1.16	71.85	18.86	[57]
B3	FTO/TiO₂/m-TiO₂/CH₃NH₃PbI₃/HTM/Au	20.90	0.91	64.00	12.10	[62]
CzPF	FTO/c-TiO₂/PCBM/MAPbI₃/HTM/Au	17.31	1.03	70.00	12.41	[60]
TPB-2F	FTO/c-TiO₂/MAPbI₃/HTM/Au	18.66	1.01	74.00	13.96	[54]
BDT2FMeDPA	FTO/c-TiO₂/mp-TiO₂/(FAPbI₃)_0.85 (MAPbBr₃)_0.15/HTM/carbon	21.40	1.00	66.00	14.50	[20]
SF-DTBT	FTO/bl-TiO₂/mp-TiO_2/MAPbI₃/HTM/Au	22.80	0.97	70.00	15.50	[55]
DF-DTBT	FTO/bl-TiO₂/mp-TiO_2/MAPbI₃/HTM/Au	22.82	1.10	74.00	18.70	[55]
JY7	FTO/c-TiO₂/CH₃NH₃PbI_3-_xCl_x/HTM/Ag	20.58	1.05	73.00	15.71	[58]
JY6	FTO/c-TiO₂/CH₃NH₃PbI_3-_xCl_x/HTM/Ag	21.39	1.07	81.00	18.54	[58]
FOMePh	FTO/bl-TiO₂/mp-TiO₂/(FAPbI₃)_0.85(MAPbBr₃)_0.15/HTM/Au	23.95	0.98	72.53	17.08	[56]
DFBT(DTS-FBTTh₂)₂	FTO/TiO₂/MAPbI₃/HTM/Au	20.70	1.10	76.00	17.30	[52]
2FBTA-2	FTO/c-TiO₂/m-TiO₂/FA_1-_xMA_xPbI₃/HTM/Au	21.53	1.06	78.62	17.94	[61]
IDIDF	FTO/bl-TiO₂/mp-TiO₂/(FAPbI₃)_0.92(MAPbBr₃)_0.08/HTM/Au	23.55	1.04	77.20	19.05	[65]
p-DTS(FBTTh₂)₂	FTO/TiO₂/MAPbI₃/HTM/Au	20.60	1.10	79.40	18.00	[53]
CB-2	FTO/c-TiO₂/mp-TiO₂/SnO₂/[(FAPbI₃)_0.87(MAPbBr₃)_0.13]_0.92-(CsPbI₃)_0.08]/HTM/Au	23.19	1.02	76.70	18.23	[64]
tpa-t-FBTD	FTO/SnO₂/(FAPbI₃)_0.85(MAPbBr₃)_0.15/HTM/Au	22.40	1.08	78.10	18.90	[59]
3,6-SFY	FTO/c-TiO₂/mp-TiO₂/FAPbI₃/HTM/Au	23.17	1.08	76.00	19.02	[63]
2,7-SFY	FTO/c-TiO₂/mp-TiO₂/FAPbI₃/HTM/Au	23.73	1.08	80.00	20.29	[63]
Spiro-oF	FTO/c-TiO₂/mp-TiO₂/FAPbI₃/HTM/Au	26.34	1.16	80.15	24.50	[51]
Spiro-mF	FTO/c-TiO₂/mp-TiO₂/FAPbI₃/HTM/Au	26.35	1.16	80.90	24.82	[51]
p-i-n devices
D43	ITO/HTM/CH₃NH₃PbI₃/PC₆₁BM/BCP/Ag	17.67	1.00	68.40	12.13	[68]
DFTAB	ITO/HTM/CH₃NH₃PbI₃/PCBM/Ag	17.50	1.07	69.00	12.40	[72]
3-F-br-4C	ITO/HTM/MAPbI₃/C₆₀/BCP/Ag	20.20	1.06	80.00	17.20	[67]
H2	ITO/HTM/CH₃NH₃PbI₃/PCBM/BCP/Ag	22.93	1.06	76.90	18.69	[19]
INIC-1F	ITO/PEDOT:PSS/MAPbI_3-_xCl_x/HTM/PCBM/PDIN/Ag	22.80	1.01	81.50	18.80	[70]
INIC-2F	ITO/PEDOT:PSS/MAPbI_3-_xCl_x/HTM/PCBM/PDIN/Ag	23.10	1.01	82.70	19.30	[70]
n-i-p devices
DFBT-MTP	ITO/HTM/MAPbI_3-_xCl_x/C₆₀/BCP/Ag	23.01	1.10	79.70	20.15	[71]
HTM-F	ITO/HTM/(FAPbI₃)_1-_x(MAPbBr₃)_x/C₆₀/BCP/Ag	23.03	1.09	82.00	20.51	[69]

HTM	Device configuration	J_sc/(mA•cm^-2)	V_oc/V	FF/%	PCE/%	Ref.
n-i-p devices
PBDT(T)[2F]T	FTO/SnO₂/MAPbI₃/HTM/Ag	16.60	1.03	68.00	11.60	[80]
PBDT[2F]T	FTO/SnO₂/MAPbI₃/HTM/Ag	22.60	1.06	72.60	17.50	[80]
R2	ITO/c-TiO₂/mp-TiO₂/MAPbBr₃/HTM/Au	23.10	0.88	66.20	13.57	[77]
P2-2F	ITO/c-TiO₂/mp-TiO₂/MAPbI₃/HTM/Au	20.17	1.04	70.65	14.94	[76]
R1	ITO/c-TiO₂/mp-TiO₂/MAPbBr₃/HTM/Au	23.70	0.98	68.30	15.88	[80]
PM6	ITO/SnO₂/ZnO/CsPbI₂Br/HTM/MoO₃/Ag	15.68	1.24	82.54	16.06	[75]
P6	ITO/c-TiO₂/mp-TiO₂/MAPbI₃/HTM/Au	20.74	1.09	75.78	17.28	[79]
PPDT2FBT	ITO/TiO₂/CH₃NH₃PbBr₃/HTM/Au	20.70	1.08	79.10	17.70	[82]
FEH	FTO/c-TiO₂/mp-TiO₂/CH₃NH₃PbI₃/FEH/Au	22.80	1.06	74.50	18.00	[83]
P3	FTO/meso-SnO₂/MAPbI₃/HTM/Au	22.90	1.11	0.80	20.30	[73]
2F-PTAA	FTO/d-TiO₂/mp-TiO₂/(FAPbI₃)_0.85(MAPbBr₃)_0.15/HTM/Au	23.40	1.13	70.30	18.60	[81]
1F-PTAA	FTO/d-TiO₂/mp-TiO₂/(FAPbI₃)_0.85(MAPbBr₃)_0.15/HTM/Au	23.40	1.14	82.30	21.20	[81]
PE8	ITO/SnO₂/(FA_0.85MA_0.15PbI₃)/HTM/MoO₃/Ag	23.90	1.12	77.60	20.80	[78]
PE9	ITO/SnO₂/(FA_0.85MA_0.15PbI₃)/HTM/MoO₃/Ag	24.10	1.15	78.20	21.70	[78]
PE10	ITO/SnO₂/(FA_0.85MA_0.15PbI₃)/HTM/MoO₃/Ag	24.10	1.16	79.80	22.30	[78]
p-i-n devices
FIAnF	ITO/HTM/(FA_0.79MA_0.16Cs_0.05)Pb(I_0.84Br_0.16)₃/C₆₀/BCP/Ag	20.67	1.04	58.00	12.19	[86]
CzAnF	ITO/HTM/(FA_0.79MA_0.16Cs_0.05)Pb(I_0.84Br_0.16)₃/C₆₀/BCP/Ag	20.73	1.03	80.00	16.81	[86]
BNo-F	ITO/HTM/MAPbI₃/PCBM/BCP/Ag	22.31	1.06	80.20	19.07	[85]
BNs-F	ITO/HTM/MAPbI₃/PCBM/BCP/Ag	22.78	1.08	83.40	20.56	[85]
PFDT-2F-COOH	ITO/HTM/FA_1–_xMA_xPbI₃/PCBM/C₆₀/BCP/Cu	24.86	1.11	78.50	21.68	[27]

HTM	Device configuration	J_sc/(mA•cm^-2)	V_oc/V	FF/%	PCE/%	Ref.
n-i-p devices
PBDT(T)[2F]T	FTO/SnO₂/MAPbI₃/HTM/Ag	16.60	1.03	68.00	11.60	[80]
PBDT[2F]T	FTO/SnO₂/MAPbI₃/HTM/Ag	22.60	1.06	72.60	17.50	[80]
R2	ITO/c-TiO₂/mp-TiO₂/MAPbBr₃/HTM/Au	23.10	0.88	66.20	13.57	[77]
P2-2F	ITO/c-TiO₂/mp-TiO₂/MAPbI₃/HTM/Au	20.17	1.04	70.65	14.94	[76]
R1	ITO/c-TiO₂/mp-TiO₂/MAPbBr₃/HTM/Au	23.70	0.98	68.30	15.88	[80]
PM6	ITO/SnO₂/ZnO/CsPbI₂Br/HTM/MoO₃/Ag	15.68	1.24	82.54	16.06	[75]
P6	ITO/c-TiO₂/mp-TiO₂/MAPbI₃/HTM/Au	20.74	1.09	75.78	17.28	[79]
PPDT2FBT	ITO/TiO₂/CH₃NH₃PbBr₃/HTM/Au	20.70	1.08	79.10	17.70	[82]
FEH	FTO/c-TiO₂/mp-TiO₂/CH₃NH₃PbI₃/FEH/Au	22.80	1.06	74.50	18.00	[83]
P3	FTO/meso-SnO₂/MAPbI₃/HTM/Au	22.90	1.11	0.80	20.30	[73]
2F-PTAA	FTO/d-TiO₂/mp-TiO₂/(FAPbI₃)_0.85(MAPbBr₃)_0.15/HTM/Au	23.40	1.13	70.30	18.60	[81]
1F-PTAA	FTO/d-TiO₂/mp-TiO₂/(FAPbI₃)_0.85(MAPbBr₃)_0.15/HTM/Au	23.40	1.14	82.30	21.20	[81]
PE8	ITO/SnO₂/(FA_0.85MA_0.15PbI₃)/HTM/MoO₃/Ag	23.90	1.12	77.60	20.80	[78]
PE9	ITO/SnO₂/(FA_0.85MA_0.15PbI₃)/HTM/MoO₃/Ag	24.10	1.15	78.20	21.70	[78]
PE10	ITO/SnO₂/(FA_0.85MA_0.15PbI₃)/HTM/MoO₃/Ag	24.10	1.16	79.80	22.30	[78]
p-i-n devices
FIAnF	ITO/HTM/(FA_0.79MA_0.16Cs_0.05)Pb(I_0.84Br_0.16)₃/C₆₀/BCP/Ag	20.67	1.04	58.00	12.19	[86]
CzAnF	ITO/HTM/(FA_0.79MA_0.16Cs_0.05)Pb(I_0.84Br_0.16)₃/C₆₀/BCP/Ag	20.73	1.03	80.00	16.81	[86]
BNo-F	ITO/HTM/MAPbI₃/PCBM/BCP/Ag	22.31	1.06	80.20	19.07	[85]
BNs-F	ITO/HTM/MAPbI₃/PCBM/BCP/Ag	22.78	1.08	83.40	20.56	[85]
PFDT-2F-COOH	ITO/HTM/FA_1–_xMA_xPbI₃/PCBM/C₆₀/BCP/Cu	24.86	1.11	78.50	21.68	[27]

氟取代有机空穴传输材料在钙钛矿太阳能电池中的应用研究进展