Research Progress of Hole Transport Materials Based on Spiro Aromatic-Skeleton in Perovskite Solar Cells

doi:10.6023/A21060253

Acta Chimica Sinica ›› 2021, Vol. 79 ›› Issue (10): 1181-1196.DOI: 10.6023/A21060253 Previous Articles Next Articles

Review

螺芳基钙钛矿太阳能电池空穴传输材料研究进展

刘庆琳^a, 任保轶^a^,^*(), 孙亚光^a^,^*(), 解令海^b, 黄维^b

a 沈阳化工大学理学院辽宁省无机分子基化学重点实验室沈阳 110142
b 南京邮电大学省部共建有机电子与信息显示国家重点实验室南京 210023

投稿日期:2021-06-07 发布日期:2021-07-12
通讯作者: 任保轶, 孙亚光

作者简介:

刘庆琳, 沈阳化工大学2020级硕士研究生, 研究方向为有机半导体分子的合成与器件性能.

任保轶, 副教授, 2000年于东北师范大学获应用化学学士学位, 并在沈阳化工大学工作至今. 2012年于东北大学获得工学博士学位. 2016年在劳伦斯伯克利国家实验室(Lawrence Berkeley National Laboratory)访学交流. 目前主要从事有机半导体材料设计和器件性能研究.

孙亚光, 博士, 沈阳化工大学教授, 现为辽宁省无机分子基化学重点实验室主任. 主要从事MOFs/COFs基微纳米晶体的多相催化和光电器件研究.

基金资助:
沈阳化工大学科学研究计划(XXLJ2019006); 营口市软科学研究计划(2020JH2/0100017); 江苏省有机电子与信息显示重点实验室—省部共建国家重点实验室培育基地开放研究基金

Research Progress of Hole Transport Materials Based on Spiro Aromatic-Skeleton in Perovskite Solar Cells

Qing-Lin Liu^a, Bao-Yi Ren^a(), Ya-Guang Sun^a(), Ling-Hai Xie^b, Wei Huang^b

a Key Laboratory of Inorganic Molecule-Based Chemistry of Liaoning Province, College of Science, Shenyang University of Chemical Technology, Shenyang 110142, China
b State Key Laboratory of Organic Electronics and Information Displays, Nanjing University of Posts & Telecommunications, Nanjing 210023, China

Received:2021-06-07 Published:2021-07-12
Contact: Bao-Yi Ren, Ya-Guang Sun
Supported by:
Science Research Plan of Shenyang University of Chemical Technology(XXLJ2019006); Soft-Science Research Plan of Yingkou City(2020JH2/0100017); Open Research Project of Key Laboratory for Organic Electronics and Information Displays

The third-generation energy electro-optical technology, perovskite solar cells (PSCs), have risen fast over the past decade. In view of the characteristic of intrinsic-semiconductor of organic-inorganic hybrid perovskite materials, as well as the multilayer planar architecture of PSC devices, the hole transport materials (HTMs) based on organic small molecules were introduced PSCs to make up of p-type layer, by which not only full-solid state PSCs were established, but also the highly efficient and stable PSC devices were attained. Currently, spiro-OMeTAD (2,2′,7,7′-tetrakis[N,N-di(4-methoxy- phenyl)amino]-9,9′-spirobifluorene) is still used as an universal benchmark material in the hole-transporting layer of PSCs, meanwhile the researches have make great effort to analyze and to improve the spiro-OMeTAD. For the prevailing molecule, the three-dimensional core of spirofluorene (SBF) offers a platform to integrate more hole-transporting units with less occupied space, and arylamine groups act as high electroactivity units due to their excellent p-type property. However, the classical SBF core has two major drawbacks: expensive preparation cost and monotonous modification positions, therefore the improvement orientation of spiro-OMeTAD is focused on the arylamine moieties. Along with the developments of molecular design of HTMs and corresponding synthetic methodology, a series of SBF-like aromatic-skeletons have been springing up and stepping into the field of HTMs in recent five years, e.g. spiro[fluorene-9,9′-xanthene], spiroacridine, spirothioxanthene and so on. These advancements expand the design space of HTM molecules, and enhance the efficiency and stability of PSCs. In consequence, we put eyes on the HTMs containing spiro aromatic-skeleton, and seek the structure elements of highly efficient materials. In this review, the high performance HTMs have been classified and summarized according to the type of spiro structure, further, their design solution and structure-performance relationship have also been refined. It is expected that the summarization and condensation would provide valuable strategies for HTMs design and promote the development of highly efficient and long-life PSCs towards practical application.

Key words: perovskite solar cell, hole transport material, spiro aromatic-skeleton, structure-performance relationship

Cite this article

Qing-Lin Liu, Bao-Yi Ren, Ya-Guang Sun, Ling-Hai Xie, Wei Huang. Research Progress of Hole Transport Materials Based on Spiro Aromatic-Skeleton in Perovskite Solar Cells[J]. Acta Chimica Sinica, 2021, 79(10): 1181-1196.

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HTMs	HOMO/eV	LUMO/eV	σ/(S•cm^-1)	μ_h/(cm²•V^-1•s^-1)	V_oc/V	J_sc/(mA•cm^-2)	FF	PCE/%	Ref.
pm-spiro-OMeTAD	–5.31	–2.31	—	—	1.01	21.1	65.2	13.9	[42]
po-spiro-OMeTAD	–5.22	–2.18	—	—	1.02	21.2	77.6	16.70	[42]
pp-spiro-OMeTAD	–5.22	–2.28	—	—	1.00	20.7	71.1	14.90	[42]
2,4-spiro-OMeTAD	–5.24	–2.08	—	—	0.956	25.6	70.1	17.20	[43]
3,4-spiro-OMeTAD	–5.26	–2.16	—	—	0.752	20.1	59.9	9.10	[43]
DM	–5.27	–2.36	—	—	1.11	24.8	81	22.30	[44]
SC	–5.26	–2.35	—	3.15×10^-3	1.15	23.47	80.6	21.76	[45]
ST	–5.31	–2.34	—	1.77×10^-3	1.06	23.05	74.4	18.18	[45]
spiro-MeTAD1	–4.49	–0.83	—	5.0×10^-3	1.109	22.57	68.7	17.20	[47]
spiro-MeTAD2	–4.55	–0.84	—	5.0×10^-3	1.119	22.42	68	17.05	[47]
CF-SP-BTh	–5.38	–3.73	—	3.14×10^-5	1.07	18.82	71	14.28	[49]
spiro-mF	–5.19	–2.23	2.60×10^-4	7.47×10^-3	1.16	26.35	81.5	24.82	[50]
spiro-oF	–5.06	–2.04	2.25×10^-4	7.29×10^-3	1.16	26.34	80.9	24.50	[50]
spiro-OMeIm	–5.13	–1.93	—	2.2×10^-4	1.1	20.35	75	16.78	[51]
spiro-TTB	–5.30	–2.23	—	1.97×10^-3	1.07	22.02	78	18.38	[48]
G1	–5.14	–2.22	9.35×10^-5	1.03×10^-4	1.08	22.01	65	15.5	[52]
Dispiro-OBuTAD	–5.16	–2.23	—	5.73×10^-3	1.08	22.79	75	18.46	[53]
spiro-F1	–5.31	–2.39	—	1.75×10^-2	—	—	—	—	[54]
spiro-F2	–5.42	–2.55	—	2.60×10^-4	—	—	—	—	[54]
spiro-F3	–5.10	–2.38	—	7.59×10^-3	—	—	—	—	[54]

HTMs	HOMO/eV	LUMO/eV	σ/(S•cm^-1)	μ_h/(cm²•V^-1•s^-1)	V_oc/V	J_sc/(mA•cm^-2)	FF	PCE/%	Ref.
pm-spiro-OMeTAD	–5.31	–2.31	—	—	1.01	21.1	65.2	13.9	[42]
po-spiro-OMeTAD	–5.22	–2.18	—	—	1.02	21.2	77.6	16.70	[42]
pp-spiro-OMeTAD	–5.22	–2.28	—	—	1.00	20.7	71.1	14.90	[42]
2,4-spiro-OMeTAD	–5.24	–2.08	—	—	0.956	25.6	70.1	17.20	[43]
3,4-spiro-OMeTAD	–5.26	–2.16	—	—	0.752	20.1	59.9	9.10	[43]
DM	–5.27	–2.36	—	—	1.11	24.8	81	22.30	[44]
SC	–5.26	–2.35	—	3.15×10^-3	1.15	23.47	80.6	21.76	[45]
ST	–5.31	–2.34	—	1.77×10^-3	1.06	23.05	74.4	18.18	[45]
spiro-MeTAD1	–4.49	–0.83	—	5.0×10^-3	1.109	22.57	68.7	17.20	[47]
spiro-MeTAD2	–4.55	–0.84	—	5.0×10^-3	1.119	22.42	68	17.05	[47]
CF-SP-BTh	–5.38	–3.73	—	3.14×10^-5	1.07	18.82	71	14.28	[49]
spiro-mF	–5.19	–2.23	2.60×10^-4	7.47×10^-3	1.16	26.35	81.5	24.82	[50]
spiro-oF	–5.06	–2.04	2.25×10^-4	7.29×10^-3	1.16	26.34	80.9	24.50	[50]
spiro-OMeIm	–5.13	–1.93	—	2.2×10^-4	1.1	20.35	75	16.78	[51]
spiro-TTB	–5.30	–2.23	—	1.97×10^-3	1.07	22.02	78	18.38	[48]
G1	–5.14	–2.22	9.35×10^-5	1.03×10^-4	1.08	22.01	65	15.5	[52]
Dispiro-OBuTAD	–5.16	–2.23	—	5.73×10^-3	1.08	22.79	75	18.46	[53]
spiro-F1	–5.31	–2.39	—	1.75×10^-2	—	—	—	—	[54]
spiro-F2	–5.42	–2.55	—	2.60×10^-4	—	—	—	—	[54]
spiro-F3	–5.10	–2.38	—	7.59×10^-3	—	—	—	—	[54]

HTMs	HOMO/eV	LUMO/eV	σ/(S•cm^-1)	μ_h/(cm²•V^-1•s^-1)	V_oc/V	J_sc/(mA•cm^-2)	FF	PCE/%	Ref.
mp-SFX-3PA	–5.08	–2.25	—	3.3×10^-5	1.00	18.94	18.9	14.05	[55]
mp-SFX-2PA	–4.92	–1.98	—	1.5×10^-4	1.02	21.17	21.2	16.77	[55]
mm-SFX-3PA	–5.08	–2.27	—	2.2×10^-5	1.01	18.02	18.0	13.25	[55]
mm-SFX-2PA	–4.89	–1.97	—	9.9×10^-5	0.97	19.07	19.1	14.10	[55]
HTM-FX	–5.17	–1.06	—	1.4×10^-4	1.16	21.2	74	18.2	[12]
HTM-F	–5.17	–1.12	—	4×10^-5	1.08	14.7	41	6.5	[12]
HTM-X	–5.26	–1.20	—	5×10^-5	0.88	3.8	32	1.1	[12]
HTM-X′	–5.47	–1.14	—	3×10^-5	0.77	1.4	26	0.2	[12]
HTM-FX′	–5.16	–1.03	—	4.8×10^-4	1.17	21.7	78	19.7	[12]
X59	–5.15	–2.10	1.9×10^-4	5.5×10^-5	1.13	23.4	23.4	19.8	[58]
BTPA-4	–5.35	–2.45	2.18×10^-4	—	0.946	18.91	51.5	9.21	[64]
BTPA-5	–5.37	–2.48	2.69×10^-4	—	0.959	18.70	63.0	11.30	[64]
BTPA-6	–5.34	–2.43	2.47×10^-4	—	0.978	20.57	57.5	11.57	[64]
SFX-OMeTAD	–5.16	–2.20	1.4×10^-5	—	0.96	21.2	21.2	11.1	[60, 61]
SFXDAnCBZ^a	–4.95	–2.16	—	4.28×10^-4	1.09	23.10	83	20.87	[63]
Y1^a	–5.35	–2.46	—	1.53×10^-4	1.05	21.35	73.9	16.29	[66]
Y2^a	–5.39	–2.59	—	3.97×10^-5	1.03	20.14	66.1	13.73	[66]
Y3^a	–5.35	–2.91	—	8.78×10^-5	0.95	10.86	76.1	15.15	[66]
X55	–5.23	–2.26	8.43×10^-4	6.81×10^-4	1.15	23.4	77	20.8	[60]
SFX-DTF1	–5.16	–2.53	—	1.51×10^-4	1.03	19.23	53.8	10.67	[68]
SFX-DTF2	–5.19	–2.57	—	3.05×10^-5	0.98	19.05	47.1	8.78	[68]
X26	–5.08	–2.22	2.79×10^-4	4.31×10^-4	1.11	24.3	75	20.2	[69]
X36	5.12	–2.14	5.05×10^-4	1.97×10^-4	1.06	23.7	76	18.9	[69]
SFX-TPAM^a	–5.21	–2.29	—	—	1.01	19.12	53	10.23	[70]
SFX-TPA^a	–5.57	–2.63	—	—	0.64	15.35	39	3.83	[70]
X60	–4.49	–2.30	1.1×10^-4	1.9×10^-4	1.12	23.4	79	20.9	[69]
spiro-p,o-OMe	–4.82	–2.38	3.7×10^-5	—	1.03	13.5	75	3.5	[25]
spiro-Me	–4.88	–2.25	2.5×10^-4	—	0.68	0.16	34	0.04	[25]
spiro-SMe	–5.09	–2.13	6.9×10^-5	—	0.92	1.25	34	0.39	[25]
spiro-FOMe	–4.96	–2.17	1.9×10^-6	—	0.77	0.04	20	0.01	[25]
spiro-H	–5.03	–2.18	2.8×10^-5	—	0.75	0.3	14	0.04	[25]
spiro-IA^a	–5.24	–2.70	2.10×10^-4	—	1.04	22.14	67.9	15.66	[71]
XDB	–5.15	–2.11	—	7. 3×10^-5	1.02	19.9	76.1	15.5	[73]
XOP	–5.15	–2.11	—	9.7×10^-5	1.06	19.6	76.5	15.9	[73]
XMP	–5.15	–2.11	—	1.3×10^-4	1.07	20.5	77.2	16.9	[73]
XPP	–5.15	–2.11	—	1.6×10^-4	1.06	21.3	78.4	17.7	[73]
X61^a	–5.11	–2.09	3.98×10^-6	3.91×10^-5	0.97	18.6	44.1	8.0	[74]
X62^a	–5.14	–2.22	5.14×10^-6	7.95×10^-5	1.01	22.4	70.4	15.9	[74]
2mF-X59	–5.14	–2.40	—	7.14×10^-5	1.01	24.97	71.6	18.13	[76,77]
SFX-o-2F	–5.16	–2.24	—	7.4×10^-6	1.12	17.59	48.8	9.7	[78]
SFX-m-2F	–5.18	–2.30	—	6.07×10^-5	1.16	22.64	71.9	18.86	[78]
SFX-p-2F	–5.18	–2.28	—	1.79×10^-5	1.14	22.23	61.5	16.33	[78]

HTMs	HOMO/eV	LUMO/eV	σ/(S•cm^-1)	μ_h/(cm²•V^-1•s^-1)	V_oc/V	J_sc/(mA•cm^-2)	FF	PCE/%	Ref.
mp-SFX-3PA	–5.08	–2.25	—	3.3×10^-5	1.00	18.94	18.9	14.05	[55]
mp-SFX-2PA	–4.92	–1.98	—	1.5×10^-4	1.02	21.17	21.2	16.77	[55]
mm-SFX-3PA	–5.08	–2.27	—	2.2×10^-5	1.01	18.02	18.0	13.25	[55]
mm-SFX-2PA	–4.89	–1.97	—	9.9×10^-5	0.97	19.07	19.1	14.10	[55]
HTM-FX	–5.17	–1.06	—	1.4×10^-4	1.16	21.2	74	18.2	[12]
HTM-F	–5.17	–1.12	—	4×10^-5	1.08	14.7	41	6.5	[12]
HTM-X	–5.26	–1.20	—	5×10^-5	0.88	3.8	32	1.1	[12]
HTM-X′	–5.47	–1.14	—	3×10^-5	0.77	1.4	26	0.2	[12]
HTM-FX′	–5.16	–1.03	—	4.8×10^-4	1.17	21.7	78	19.7	[12]
X59	–5.15	–2.10	1.9×10^-4	5.5×10^-5	1.13	23.4	23.4	19.8	[58]
BTPA-4	–5.35	–2.45	2.18×10^-4	—	0.946	18.91	51.5	9.21	[64]
BTPA-5	–5.37	–2.48	2.69×10^-4	—	0.959	18.70	63.0	11.30	[64]
BTPA-6	–5.34	–2.43	2.47×10^-4	—	0.978	20.57	57.5	11.57	[64]
SFX-OMeTAD	–5.16	–2.20	1.4×10^-5	—	0.96	21.2	21.2	11.1	[60, 61]
SFXDAnCBZ^a	–4.95	–2.16	—	4.28×10^-4	1.09	23.10	83	20.87	[63]
Y1^a	–5.35	–2.46	—	1.53×10^-4	1.05	21.35	73.9	16.29	[66]
Y2^a	–5.39	–2.59	—	3.97×10^-5	1.03	20.14	66.1	13.73	[66]
Y3^a	–5.35	–2.91	—	8.78×10^-5	0.95	10.86	76.1	15.15	[66]
X55	–5.23	–2.26	8.43×10^-4	6.81×10^-4	1.15	23.4	77	20.8	[60]
SFX-DTF1	–5.16	–2.53	—	1.51×10^-4	1.03	19.23	53.8	10.67	[68]
SFX-DTF2	–5.19	–2.57	—	3.05×10^-5	0.98	19.05	47.1	8.78	[68]
X26	–5.08	–2.22	2.79×10^-4	4.31×10^-4	1.11	24.3	75	20.2	[69]
X36	5.12	–2.14	5.05×10^-4	1.97×10^-4	1.06	23.7	76	18.9	[69]
SFX-TPAM^a	–5.21	–2.29	—	—	1.01	19.12	53	10.23	[70]
SFX-TPA^a	–5.57	–2.63	—	—	0.64	15.35	39	3.83	[70]
X60	–4.49	–2.30	1.1×10^-4	1.9×10^-4	1.12	23.4	79	20.9	[69]
spiro-p,o-OMe	–4.82	–2.38	3.7×10^-5	—	1.03	13.5	75	3.5	[25]
spiro-Me	–4.88	–2.25	2.5×10^-4	—	0.68	0.16	34	0.04	[25]
spiro-SMe	–5.09	–2.13	6.9×10^-5	—	0.92	1.25	34	0.39	[25]
spiro-FOMe	–4.96	–2.17	1.9×10^-6	—	0.77	0.04	20	0.01	[25]
spiro-H	–5.03	–2.18	2.8×10^-5	—	0.75	0.3	14	0.04	[25]
spiro-IA^a	–5.24	–2.70	2.10×10^-4	—	1.04	22.14	67.9	15.66	[71]
XDB	–5.15	–2.11	—	7. 3×10^-5	1.02	19.9	76.1	15.5	[73]
XOP	–5.15	–2.11	—	9.7×10^-5	1.06	19.6	76.5	15.9	[73]
XMP	–5.15	–2.11	—	1.3×10^-4	1.07	20.5	77.2	16.9	[73]
XPP	–5.15	–2.11	—	1.6×10^-4	1.06	21.3	78.4	17.7	[73]
X61^a	–5.11	–2.09	3.98×10^-6	3.91×10^-5	0.97	18.6	44.1	8.0	[74]
X62^a	–5.14	–2.22	5.14×10^-6	7.95×10^-5	1.01	22.4	70.4	15.9	[74]
2mF-X59	–5.14	–2.40	—	7.14×10^-5	1.01	24.97	71.6	18.13	[76,77]
SFX-o-2F	–5.16	–2.24	—	7.4×10^-6	1.12	17.59	48.8	9.7	[78]
SFX-m-2F	–5.18	–2.30	—	6.07×10^-5	1.16	22.64	71.9	18.86	[78]
SFX-p-2F	–5.18	–2.28	—	1.79×10^-5	1.14	22.23	61.5	16.33	[78]

HTMs	HOMO/eV	LUMO/eV	σ/(S•cm^-1)	μ_h/(cm²•V^-1•s^-1)	V_oc/V	J_sc/(mA•cm^-2)	FF	PCE/%	Ref.
CW3	–4.92	–1.89	5.92×10^-6	1.2×10^-4	0.99	16.49	67	10.94	[81]
CW4	–4.92	–1.88	3.54×10^-6	5.8×10^-5	1.05	21.75	72	16.56	[81]
CW5	–4.93	–1.89	3.09×10^-6	8.7×10^-5	1.01	15.39	70	10.76	[81]
SAF-OMe^a	–5.07	–2.11	—	9.9×10^-4	0.97	20.59	62	17.39	[82]
SAF-5	–5.02	–2.05	—	1.73×10^-4	1.07	20.41	63	13.93	[82]
SFT-TPAM^a	–5.69	–2.81	—	—	1.04	12.17	25	3.16	[70]
SFT-TPA^a	–5.71	–2.78	—	—	0.68	11.32	37	2.85	[70]
ST	–5.16	–2.02	—	4.75×10^-5	—	—	—	—	[84]
ST2	–5.14	–1.95	—	1.82×10^-4	—	—	—	—	[84]
DDOF	–5.07	–2.05	—	—	1.10	22.37	79	19.4	[85]
G2	–5.22	–2.27	2.77×10^-4	3.58×10^-4	1.13	23.52	76	20.2	[52, 86]

螺芳基钙钛矿太阳能电池空穴传输材料研究进展

Research Progress of Hole Transport Materials Based on Spiro Aromatic-Skeleton in Perovskite Solar Cells

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