journal article·2020-04Open access

Hole transporting materials for perovskite solar cells: molecular versus polymeric carbazole-based derivatives

Diego Magaldi, Maria Ulfa, Mai-Phuong Nghiêm, Gjergji Sini, Fabrice Goubard, Thierry Pauporté, Thanh-Tuân Bui

Journal of Materials Science· Volume 55· Issue 11

Abstract

Designing organic hole transporting materials (HTMs) for stable perovskite photovoltaic devices remains a great challenge. Herein, we have prepared two small carbazole-based HTMs bearing a polymerizable double bond and one of the corresponding polymers. All compounds can be easily synthetized by a short procedure from largely available commercial products. These compounds have thermal, morphological, optical and electrochemical properties suitable for an application in perovskite solar cells. The side chains at the N-position on the carbazole have a negligible influence on the opto-electrochemical properties. However, the thermal properties differ largely between the monomer and its corresponding polymer. While these materials have the same photovoltaic performance, the polymeric HTM led to more stable devices. This illustrates the higher thermal stability of polymeric HTM versus its corresponding monomer.
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Research context

OpenAlex topics: Perovskite Materials and Applications · Organic Light-Emitting Diodes Research · Conducting polymers and applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (41)

Show source-provided references
1. Calió L, Momblona C, Gil-Escrig L, Kazim S, Sessolo M, Sastre-Santos Á, Bolink HJ, Ahmad S (2017) Vacuum deposited perovskite solar cells employing dopant-free triazatruxene as the hole transport material. Sol Energy Mater Sol Cells 163:237–241. https://doi.org/10.1016/j.solmat.2017.01.03710.1016/j.solmat.2017.01.037 ↗
2. Bui T-T, Shah SKSK, Abbas M, Sallenave X, Sini G, Hirsch L, Goubard F (2015) Carbazole-based molecular glasses as hole-transporting materials in solid state dye-sensitized solar cells. ChemNanoMat 1(3):203–210. https://doi.org/10.1002/cnma.20150001410.1002/cnma.201500014 ↗
3. Bui T-T, Goubard F (2013) Recent advances in small molecular, non-polymeric organic hole transporting materials for solid-state DSSC. EPJ Photovolt 4:40402. https://doi.org/10.1051/epjpv/201302410.1051/epjpv/2013024 ↗
4. Bui TT, Beouch L, Sallenave X, Goubard F (2013) Carbazol-N-Yl and diphenylamino end-capped triphenylamine-based molecular glasses: synthesis, thermal, and optical properties. Tetrahedron Lett 54(32):4277–428010.1016/j.tetlet.2013.05.152 ↗
5. Xue Y, Wu Y, Li Y (2017) Readily synthesized dopant-free hole transport materials with phenol core for stabilized mixed perovskite solar cells. J Power Sources 344:160–169. https://doi.org/10.1016/j.jpowsour.2017.01.12110.1016/j.jpowsour.2017.01.121 ↗
6. Al Mousawi A, Lara DM, Noirbent G, Dumur F, Toufaily J, Hamieh T, Bui T-T, Goubard F, Graff B, Gigmes D et al (2017) Carbazole derivatives with thermally activated delayed fluorescence property as photoinitiators/photoredox catalysts for LED 3D printing technology. Macromolecules 50(13):4913–4926. https://doi.org/10.1021/acs.macromol.7b0111410.1021/acs.macromol.7b01114 ↗
7. Al Mousawi A, Dumur F, Garra P, Toufaily J, Hamieh T, Goubard F, Bui T-T, Graff B, Gigmes D, Pierre Fouassier J et al (2017) Azahelicenes as visible light photoinitiators for cationic and radical polymerization: preparation of photoluminescent polymers and use in high performance LED projector 3D printing resins. J Polym Sci Part A Polym Chem 55(7):1189–1199. https://doi.org/10.1002/pola.2847610.1002/pola.28476 ↗
8. Bui T-T, Goubard F, Ibrahim-Ouali M, Gigmes D, Dumur F (2018) Thermally activated delayed fluorescence emitters for deep blue organic light emitting diodes: a review of recent advances. Appl Sci 8(4):494. https://doi.org/10.3390/app804049410.3390/app8040494 ↗
9. Bui T-T, Goubard F, Ibrahim-Ouali M, Gigmes D, Dumur F (2018) Recent advances on organic blue thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs). Beilstein J Org Chem 14(1):282–308. https://doi.org/10.3762/bjoc.14.1810.3762/bjoc.14.18 ↗
10. Sathiyan G, Sivakumar EKT, Ganesamoorthy R, Thangamuthu R, Sakthivel P (2016) Review of carbazole based conjugated molecules for highly efficient organic solar cell application. Tetrahedron Lett 57(3):243–252. https://doi.org/10.1016/j.tetlet.2015.12.05710.1016/j.tetlet.2015.12.057 ↗
11. Di Giacomo F, Zardetto V, D’Epifanio A, Pescetelli S, Matteocci F, Razza S, Di Carlo A, Licoccia S, Kessels WMM, Creatore M et al (2015) Flexible perovskite photovoltaic modules and solar cells based on atomic layer deposited compact layers and UV-irradiated TiO2 scaffolds on plastic substrates. Adv Energy Mater 5(8):1401808. https://doi.org/10.1002/aenm.20140180810.1002/aenm.201401808 ↗
12. Kim HS, Jang IH, Ahn N, Choi M, Guerrero A, Bisquert J, Park NG (2015) Control of I–V hysteresis in CH3NH3PbI3 perovskite solar cell. J Phys Chem Lett 6(22):4633–4639. https://doi.org/10.1021/acs.jpclett.5b0227310.1021/acs.jpclett.5b02273 ↗
13. Ulfa M, Zhu T, Goubard F, Pauporté T (2018) Molecular versus polymeric hole transporting materials for perovskite solar cell application. J Mater Chem A 6(27):13350–13358. https://doi.org/10.1039/C8TA03875A10.1039/C8TA03875A ↗
14. Hsu C-Y, Chen Y-C, Lin RY-Y (2012) Solid-state dye-sensitized solar cells based on spirofluorene (Spiro-OMeTAD) and arylamines as hole transporting materials. Phys Chem Chem Phys 14(41):14099–14109. https://doi.org/10.1039/c2cp41326d10.1039/c2cp41326d ↗
15. Holliday S, Donaghey JE, McCulloch I (2014) Advances in charge carrier mobilities of semiconducting polymers used in organic transistors. Chem Mater 26(1):647–663. https://doi.org/10.1021/cm402421p10.1021/cm402421p ↗
16. Arias AC, MacKenzie JD, McCulloch I, Rivnay J, Salleo A (2010) Materials and applications for large area electronics: solution-based approaches. Chem Rev 110(1):3–24. https://doi.org/10.1021/cr900150b10.1021/cr900150b ↗
17. Zaumseil J, Sirringhaus H (2007) Electron and ambipolar transport in organic field-effect transistors. Chem Rev 107(4):1296–1323. https://doi.org/10.1021/CR050154310.1021/CR0501543 ↗
18. Bui T-T, Shah SK, Sallenave X, Abbas M, Sini G, Hirsch L, Goubard F (2015) Di(p-methoxyphenyl)amine end-capped tri(p-thiophenylphenyl)amine based molecular glasses as hole transporting materials for solid-state dye-sensitized solar cells. RSC Adv 5(61):49590–49597. https://doi.org/10.1039/c5ra07226c10.1039/c5ra07226c ↗
19. Bui T-T, Goubard F, Troughton J, Watson T (2017) Simple 3,6-bis(diphenylaminyl)carbazole molecular glasses as hole transporting materials for hybrid perovskite solar cells. J Mater Sci Mater Electron 28(23):17551–17556. https://doi.org/10.1007/s10854-017-7691-y10.1007/s10854-017-7691-y ↗
20. Cho A-N, Kim H-S, Bui T-T, Sallenave X, Goubard F, Park N-G (2016) Role of LiTFSI in High Tg triphenylamine-based hole transporting material in perovskite solar cell. RSC Adv 6(72):68553–68559. https://doi.org/10.1039/c6ra12574c10.1039/c6ra12574c ↗
21. Daskeviciene M, Paek S, Wang Z, Malinauskas T, Jokubauskaite G, Rakstys K, Cho KT, Magomedov A, Jankauskas V, Ahmad S et al (2017) Carbazole-based enamine: low-cost and efficient hole transporting material for perovskite solar cells. Nano Energy 32:551–557. https://doi.org/10.1016/j.nanoen.2017.01.01510.1016/j.nanoen.2017.01.015 ↗
22. Rakstys K, Paek S, Gao P, Gratia P, Marszalek T, Grancini G, Cho KT, Genevicius K, Jankauskas V, Pisula W et al (2017) Molecular engineering of face-on oriented dopant-free hole transporting material for perovskite solar cells with 19% PCE. J Mater Chem A 5(17):7811–7815. https://doi.org/10.1039/C7TA01718A10.1039/C7TA01718A ↗
23. Zhang M-D, Zheng B-H, Zhuang Q-F, Huang C-Y, Cao H, Chen M-D, Wang B (2017) Two dimethoxyphenylamine-substituted carbazole derivatives as hole-transporting materials for efficient inorganic-organic hybrid perovskite solar cells. Dye Pigment 146:589–595. https://doi.org/10.1016/J.DYEPIG.2017.07.03710.1016/J.DYEPIG.2017.07.037 ↗
24. Zhao X, Wang M (2018) Organic hole-transporting materials for efficient perovskite solar cells. Mater Today Energy 7:208–220. https://doi.org/10.1016/j.mtener.2017.09.01110.1016/j.mtener.2017.09.011 ↗
25. Berton N, Nakar R, Schmaltz B (2019) DMPA-containing carbazole-based hole transporting materials for perovskite solar cells: recent advances and perspectives. Synth Metals. https://doi.org/10.1016/j.synthmet.2019.04.00410.1016/j.synthmet.2019.04.004 ↗
26. Torres A, Rego LGC (2014) Surface effects and adsorption of methoxy anchors on hybrid lead iodide perovskites: insights for Spiro-MeOTAD attachment. J Phys Chem C 118(46):26947–26954. https://doi.org/10.1021/jp510595s10.1021/jp510595s ↗
27. Bui T-T, Ulfa M, Maschietto F, Ottochian A, Nghiêm M-P, Ciofini I, Goubard F, Pauporté T (2018) Design of dendritic core carbazole-based hole transporting materials for efficient and stable hybrid perovskite solar cells. Org Electron 60:22–30. https://doi.org/10.1016/j.orgel.2018.05.02410.1016/j.orgel.2018.05.024 ↗
28. Ulfa M, Pauporte T, Bui T-T, Goubard F (2018) Impact of organic hole transporting material and doping on the electrical response of perovskite solar cells. J Phys Chem C 122(22):11651–11658. https://doi.org/10.1021/acs.jpcc.8b0214110.1021/acs.jpcc.8b02141 ↗
29. Abdallah M, Magaldi D, Hijazi A, Graff B, Dumur F, Fouassier J, Bui T, Goubard F, Lalevée J (2019) Development of new high-performance visible light photoinitiators based on carbazole scaffold and their applications in 3D printing and photocomposite synthesis. J Polym Sci Part A Polym Chem. https://doi.org/10.1002/pola.2947110.1002/pola.29471 ↗
30. Konishi A, Yoda N, Marvel CS (1965) Base-catalyzed polymerization of p-styrenesulfonamides. II. N-methyl and N-phenyl derivatives. J Polym Sci Part A Gen Pap 3(11):3833–3842. https://doi.org/10.1002/pol.1965.10003111410.1002/pol.1965.100031114 ↗
31. Jenkins AD, Jones RG, Moad G (2009) Terminology for reversible-deactivation radical polymerization previously called “controlled” radical or “living” radical polymerization (IUPAC Recommendations 2010). Pure Appl Chem 82(2):483–491. https://doi.org/10.1351/PAC-REP-08-04-0310.1351/PAC-REP-08-04-03 ↗
32. Mayo FR (1943) Chain transfer in the polymerization of styrene: the reaction of solvents with free radicals1. J Am Chem Soc 65(12):2324–2329. https://doi.org/10.1021/ja01252a02110.1021/ja01252a021 ↗
33. Flory PJ (1937) The mechanism of vinyl polymerizations. J Am Chem Soc 59(2):241–253. https://doi.org/10.1021/ja01281a00710.1021/ja01281a007 ↗
34. Furuncuoǧlu T, Uǧur I, Degirmenci I, Aviyente V (2010) Role of chain transfer agents in free radical polymerization kinetics. Macromolecules 43(4):1823–1835. https://doi.org/10.1021/ma902803p10.1021/ma902803p ↗
35. Matyjaszewski K, Davis TP (2002) Handbook of radical polymerization, vol 125. John Wiley & Sons, Inc., USA. https://doi.org/10.1002/047122045010.1002/0471220450 ↗
36. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA et al (2009) Gaussian, Inc., Wallingford CT. Gaussian, Inc., Wallingford, p 2009
37. Chai JD, Head-Gordon M (2008) Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys Chem Chem Phys 10(44):6615–6620. https://doi.org/10.1039/b810189b10.1039/b810189b ↗
38. Pommerehne J, Vestweber H, Guss W, Mahrt RF, Bässler H, Porsch M, Daub J (1995) Efficient two layer leds on a polymer blend basis. Adv Mater 7(6):551–554. https://doi.org/10.1002/adma.1995007060810.1002/adma.19950070608 ↗
39. Cardona CM, Li W, Kaifer AE, Stockdale D, Bazan GC (2011) Electrochemical considerations for determining absolute frontier orbital energy levels of conjugated polymers for solar cell applications. Adv Mater 23(20):2367–2371. https://doi.org/10.1002/adma.20100455410.1002/adma.201004554 ↗
40. Wang P, Ulfa M, Pauporté T (2018) Effects of perovskite monovalent cation composition on the high and low frequency impedance response of efficient solar cells. J Phys Chem C 122(4):1973–1981. https://doi.org/10.1021/acs.jpcc.7b1101010.1021/acs.jpcc.7b11010 ↗
41. Zhao X, Kim HS, Seo JY, Park NG (2017) Effect of selective contacts on the thermal stability of perovskite solar cells. ACS Appl Mater Interfaces 9(8):7148–7153. https://doi.org/10.1021/acsami.6b1567310.1021/acsami.6b15673 ↗