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Home > Materials > Hole transport materials and dopants

Hole transport materials and dopants

Hole transport materials (HTMs) are one of the key compounds in perovskite solar cells (PSCs), both for the n-i-p and the p-i-n device structures. HTMs can also be used to replace the liquid electrolyte of conventional dye-sensitized solar cells to make solid-state DSSC (ss-DSSC) devices. Dyenamo offers a selection of hole conductors and dopants allowing the user to find the material best suited for their application and device technology. For larger amounts than the ones displayed, please contact us. Likewise, please contact us for consultation services on how to use our hole conductors in an optimized manner.

Further strategic Dyenamo material-components for perovskite solar cells can be found in the product categories: Perovskite precursors and additives, Carbon pastes, TiO2 and platinum pastes and FTO glass.

Overview

Product code Name HOMO (eV) LUMO (eV) Mobility (cm2 V-1 s-1) λabs (nm) Recommended use
DN-X01 X51 -5.14 -2.21 1.5*10-4 365 HTM for n-i-p PSC, ss-DSSC
DN-X02 X60 -5.15 -2.10 1.9*10-4 387 HTM for n-i-p PSC, ss-DSSC
DN-X03 X59 -5.15 -2.10 5.5*10-5 387 HTM for n-i-p PSC
DN-X04 TPAA -5.35 - - - HTM for n-i-p PSC, ss-DSSC
DN-X05 PTAA -5.20 -2.30 1.0*10-3 395 HTM for n-i-p PSC, ss-DSSC
DN-X06 X44 -5.06 -2.12 9.0*10-4 381 HTM for n-i-p PSC
DN-X07 X55 -5.23 -2.26 6.8*10-4 402 HTM for n-i-p PSC, p-i-n PSC
DN-X08 X62 -5.14 -2.22 7.9*10-5 383 HTM for n-i-p PSC
DN-X09 2PACz - - - - HTM for p-i-n PSC
DN-X10 DFH -5.27 -2.29 1.0*10-3 370 HTM for p-i-n PSC
DN-X11 TaTm -5.40 -2.35 4.0*10-4 390 HTM for p-i-n PSC
DN-EVH01 Spiro-OMeTAD -5.13 -2.06 8.1*10-5 388 HTM for n-i-p PSC, p-i-n PSC
DN-P03 FK102 - - - - p-type dopant for HTMs
DN-P04 FK209 - - - - p-type dopant for HTMs
DN-P16 F4TCNQ -8.34 -5.24 - - p-type dopant for HTMs
DN-P17 Zn(TFSI)2 - - - - p-type dopant for HTMs
DN-P20 F6-TCNNQ -9.32 -5.37 - - p-type dopant for HTMs




DN-X01

X51

Description:
X51 is a high-performance carbazole-based hole transport material (HTM) suitable for use in DSSC's and perovskite solar cells. In combination with a metal-free dye such as DN-F05, device power conversion efficiencies exceeding that of Spiro-OMeTAD has been achieved.

Full name:
9,9'-([1,1'-biphenyl]-4,4'-diyl)bis(N3,N3,N6,N6-tetrakis(4-methoxyphenyl)-9H-carbazole-3,6-diamine)

CAS number:
1630723-99-7

Typical properties:
HOMO = -5.14 eV
LUMO = -2.21 eV
Eox (DCM) = 0.64 V vs. NHE
Hole mobility = 1.5*10-4 cm2 V-1 s-1
λabs (DCM) = 365 nm, 307 nm (max)
MW = 1393.65 g/mol
Reorganization energy = 378 meV (calc.)

Recommended device concept:
• n-i-p Perovskite solar cells
• solid-state DSSC

References:
• Bo Xu, et al., Adv. Mater., 2014, DOI: 10.1002/adma.201402415









DN-X02

X60

Description:
X60 is a high-performance hole transport material highly that has proven itself as an economical replacement for spiro-OMeTAD in both perovskite and solid-state dye-sensitized solar cells with demonstrated efficiencies of 19.8 and 7.3% respectively.

Full name:
octakis(4-methoxyphenyl)spiro[fluorene-9,9'-xanthene]-2,2',7,7'-tetraamine)

CAS number:
1887794-22-0

Typical properties:
HOMO = -5.15 eV
LUMO = -2.10 eV
Eox (DCM) = 0.65 V vs. NHE
Hole mobility = 1.9*10-4 cm2 V-1 s-1
λabs = 387 nm
MW = 1241.45 g/mol

Recommended device concept:
• n-i-p Perovskite solar cells
• solid-state DSSC

References:
• Bo Xu, et al., Energy & Environmental Science, 2016, DOI: 10.1039/C6EE00056H



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DN-X03

X59

Description:
X59 is a high-performance hole transport material that has proven itself as an economical replacement for spiro-OMeTAD in perovskite solar cells with a demonstrated efficiency of 19.8%.

Full name:
N2,N2,N7,N7-tetrakis(4-methoxyphenyl)spiro[fluorene-9,9'-xanthene]-2,7-diamine

CAS number:
2095034-97-0

Typical properties:
HOMO = -5.15 eV
LUMO = -2.10 eV
Eox (DCM) = 0.65 V vs. NHE
Hole mobility = 5.5*10-5 cm2 V-1 s-1
λabs (PhMe) = 387 nm
MW = 786.93 g/mol

Recommended device concept:
• n-i-p Perovskite solar cells

References:
• Dongqin Bi, et al., Nano Energy, 2016, DOI: 10.1016/j.nanoen.2016.03.020

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DN-X04

tris(4-methoxyphenyl)amine

Description:
Tris(4-methoxyphenyl)amine is a small and versatile redox-active molecule which can be employed in both liquid and solid-state solar cells. In DSSCs with liquid electrolyte it can be used together with a metal-based redox couple to enable exceptionally fast dye regeneration, giving easy access to >10% efficiencies. In solid-state solar cells it may be used as a low cost hole-transporting material, either by itself or combined with another material such as P3HT.

Alternative name:
TPAA, TAA, tris(p-anisyl)amine, tris(para-anisyl)amine

CAS number:
13050-56-1

Typical properties:
Eox (DCM) = 0.85 V vs. NHE
MW = 335.40 g/mol

Recommended device concept:
• n-i-p Perovskite solar cells
• solid-state DSSC

References:
• J. Phys. Chem. C 2012, 116, 18070-18078, DOI: 10.1021/jp3052449
Chem. Mater., 2001, 13 (11), pp 4105-4111, DOI: 10.1021/cm010281p
• Nature Commun. 7 (2016) 13934, DOI: 10.1038/ncomms13934





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DN-X05

Poly(triaryl amine)



Description:
p-type polymeric semiconductor used in perovskite solar cells, OLEDs and other organic electronics applications. In perovskite solar cells it has been used with great success, enabling efficiencies in excess of 20%. More recently, it has also been shown that PTAA plays an important part in making highly stable perovskite solar cells by preventing metal atoms from the electrode from diffusing into the perovskite.

Full name:
Poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine]

Alternative name:
PTAA

CAS number:
1333317-99-9

Typical properties:
HOMO = -5.20 eV
LUMO = -2.30 eV
Hole mobility = 1.0*10-3 cm2 V-1 s-1
λabs = 395 nm
Mn = 22000 g/mol

Recommended device concept:
• n-i-p Perovskite solar cells
• solid-state DSSC

References:
• Michael Saliba, et al., Science, 2016, DOI: 10.1126/science.aah5557
• Woon Seok Yang, et al., Science, 2015, DOI: 10.1126/science.aaa9272
• Jin Hyuck Heo, et al., Nature Photonics, 2013, DOI: 10.1038/nphoton.2013.80





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DN-X06

X44

Description:
A dopant-free ionic hole transport material suitable for use in perovskite solar cells. By avoiding dopants good stability and improved reproducibility can be achieved. Through the introduction of quarternary amine functional groups permanent charges are incorporated into the material. DN-X06 displays an order of magnitude higher hole conductivity compared to undoped spiro-OMeTAD.

Full name:
3,3'-(2,7-bis(bis(4-methoxyphenyl)amino)-9H-fluorene-9,9-diyl)bis(N-ethyl-N,N-dimethylpropan-1-aminium) bis[bis((trifluoromethyl)sulfonyl)amide]

Typical properties:
HOMO = -5.06 eV
LUMO = -2.12 eV
Eox (DCM) = 0.62 V vs NHE
Hole mobility = 9.0*10-4 S cm-1
λabs (DCM) = 381 nm
MW = 1409.44 g/mol

Recommended device concept:
• n-i-p Perovskite solar cells

References:
• J. Zhang, et al., Adv. Energy Mater, 2017, DOI: 10.1002/aenm.201602736

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DN-X07

X55

Description:
A high-performance pinhole-free hole-transport materials with excellent film forming ability, suitable for use in both n-i-p and p-i-n structured perovskite solar cells, with demonstrated device efficiencies of up to 20.8%.

Full name:
N2,N7-bis(4-methoxyphenyl)-N2,N7-di(spiro[fluorene-9,9'-xanthen]-2-yl)spiro[fluorene-9,9'-xanthene]-2,7-diamine

Typical properties:
HOMO = -5.23 eV
LUMO = -2.26 eV
Eox (DCM) = 0.73 V vs NHE
Hole mobility = 6.8*10-4 S cm-1
λabs = 402 nm
MW = 1235.45 g/mol

Suggestions for use:
The suggested concentration of X55 in n-i-p structured perovskite solar cells is around 30-40 mg in 1 ml chlorobenzene. The concentration of additives, such as tBP, LiTFSI and dopants can be kept the same as with Spiro-OMeTAD. The oxidation potential of X55 (0.73 V) is higher than that of Spiro-OMeTAD (0.63 V), so the oxygen doping method is not so efficient. Instead, a chemical dopant is recommended, such as FK209 or AgTFSI. For p-i-n structured perovskite solar cells the suggested concentration is around 15-20 mg in 1 ml chlorobenzene, and no additives are needed. The Dyenamo team offers consultation services on how to use X55 to make high efficiency perovskite solar cells. You are very welcome to contact us.

Recommended device concept:
• n-i-p Perovskite solar cells
• p-i-n Perovskite solar cells

References:
• B. Xu, et al., Chem, 2017, DOI: 10.1016/j.chempr.2017.03.011

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DN-X08

X62

Description:
A dopant-free hole transport material with a spiro[dibenzo[c,h]xanthene-7,9′-fluorene] (SDBXF) core. Demonstrated efficiency of 15.9% in perovskite solar cells without dopants (undoped Spiro-OMeTAD-based devices, 10.8%).

Full name:
N2',N2',N5,N5,N7',N7',N9,N9-octakis(4-methoxyphenyl)spiro[dibenzo- [c,h]xanthene-7,9'-fluorene]-2',5,7',9-tetraamine

Typical properties:
HOMO = -5.14 eV
LUMO = -2.22 eV
Eox (DCM) = 0.67 V vs NHE
Hole mobility = 7.9*10-5 cm2 V-1 s-1
λabs (DCM) = 383 nm
MW = 1341.57 g/mol

Recommended device concept:
• n-i-p Perovskite solar cells

References:
• Chem. Commun., 2018, 54, 9571. DOI: 10.1016/10.1039/c8cc04026e

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DN-X09

2PACz

Description:
DN-X09 is a carbazole-based molecule with phosphonic acid as the anchoring group that can form self-assembled monolayers (SAMs) on various oxides. The SAMs can create an energetically aligned interface to the perovskite absorber without non-radiative losses. Demonstrated high power conversion efficiency (PCE) of 21.1% and 23.26% in inverted p-i-n perovskite solar cells and monolithic CIGSe/perovskite tandem solar cells, respectively.

Full name:
(2-(9H-carbazol-9-yl)ethyl)phosphonic acid

CAS number:
20999-38-6

Typical properties:
λabs (on ITO glass) = 340 nm
MW = 275.24 g/mol

Recommended device concept:
• p-i-n Perovskite solar cells

References:
• Amran Ashouri, et al., Energy & Environmental Science, 2019, DOI: 10.1039/c9ee02268f

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DN-X10

DFH

Description:
A high performance dopant-free small molecule hole transport material suitable for use in inverted p-i-n type perovskite solar cells. DN-X10 shows high intrinsic hole mobility (1 * 10-3 cm2 V-1 s-1) in thin film due to the strong intermolecular interactions of the dioxane groups in the structure. Demonstrated high-power conversion efficiency (PCE) of 20.6% in an inverted (p-i-n) PSC without any dopants or interlayers.

Full name:
N2,N2,N7,N7-tetra-p-tolylspiro[fluorene-9,2'-[1,3]dioxolane]-2,7-diamine

Typical properties:
HOMO = -5.27 eV
LUMO = -2.29 eV
Hole mobility = 1 * 10-3 cm2 V-1 s-1
λabs (DCM) = 370 nm
MW = 614.79 g/mol

Recommended device concept:
• p-i-n Perovskite solar cells

References:
• Yang Cao, et al., Energy & Environmental Science, 2019, DOI: 10.1039/C9EE02983D

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DN-X11

TaTm

Description:
DN-X11 is a high performance vacuum deposited small molecule hole transport material that is suitable for use in inverted p-i-n type perovskite solar cells. DN-X11 has high thermal stability and intrinsic hole mobility (4 * 10-3 cm2 V-1 s-1). Demonstrated high-power conversion efficiency (PCE) of 20 % in vacuum deposited inverted (p-i-n) PSCs.

Full name:
N4,N4,N4'',N4''-tetra([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4,4''-diamine

CAS number:
952431-34-4

Typical properties:
HOMO = -5.40 eV
LUMO = -2.35 eV
Hole mobility = 4 * 10-3 cm2 V-1 s-1
MW = 869.12 g/mol

Recommended device concept:
• p-i-n Perovskite solar cells

References:
• Cristina Momblona, et al., Energy & Environmental Science, 2016, DOI: 10.1039/c6ee02100j


DN-EVH01

Eversolar® Spiro-OMeTAD

Description:
Spiro-OMeTAD is the reference hole-transport material for solid-state DSSCs and Perovskite solar cells.

Full name:
2,2',7,7'-Tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene

CAS number:
207739-72-8

Typical properties:
HOMO = -5.13 eV
LUMO = -2.06 eV
Hole mobility = 8.1*10-5 cm2 V-1 s-1
λabs.max = 388 nm
MW = 1225.43 g/mol

Recommended device concept:
• n-i-p Perovskite solar cells
• p-i-n Perovskite solar cells

Additional information:
Dyenamo is European distributor of Everlight's hole transport materials.

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DN-P03

FK102

Description:
Cobalt-based p-type dopant for organic hole conductors, such as spiro-MeOTAD

Full name:
Tris(2-(1H-pyrazol-1-yl)pyridine)cobalt(III) tri(hexafluorophosphate)

CAS number:
1346416-70-3

Typical properties:
MW = 929.32 g/mol

Specification:
Product specification DN-P03: FK102

Reference:
• J. Burschka et al., J. Am. Chem. Soc. 2011, 133, 18042-18045 DOI: 10.1021/ja207367t


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DN-P04

FK209

Description:
Cobalt-based p-type dopant for organic hole conductors, such as spiro-MeOTAD

Full name:
Tris(2-(1H-pyrazol-1-yl)-4-tert-butylpyridine)-cobalt(III) Tris(bis(trifluoromethylsulfonyl)imide)

CAS number:
1447938-61-5

Typical properties:
MW = 1503.16 g/mol

Specification:
Product specification DN-P04: FK209

Reference:
• Julian Burschka, et al. Chem. Mater. 25, 2986 (2013) DOI: 10.1021/cm400796u



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DN-P16

F4TCNQ

Description:
F4TCNQ is a strong molecular p-type dopant with a very wide range of applications stretching from perovskite solar cells to OPV, OLED and OFET. In 2018 it was demonstrated that adding a low (0.03%) concentration of F4TCNQ to the perovskite precursor solution enables the fabrication of >20% efficient HTM-free PSCs (ITO/perovskite/ETL/Cu structure). The F4TCNQ offered by Dyenamo is a high purity (>99%) sublimed grade material.

Chemical name:
2,2'-(perfluorocyclohexa-2,5-diene-1,4-diylidene)dimalononitrile

Alternative name:
2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane, F4-TCNQ

Empirical Formula:
C12F4N4

CAS number:
29261-33-4

Typical properties:
LUMO = -5.24 eV
HOMO = -8.34 eV
Mw = 276.15 g/mol

Reference:
• Nature Communications, 2018, 1625 (9), DOI: 10.1038/s41467-018-04028-8
DN-P16


DN-P17

Zn(TFSI)2

Description:
Zn(TFSI)2 can be used in place of LiTFSI as a p-type dopant for hole transport materials in perovskite solar cells. Substantial benefits over LiTFSI in terms of device performance and stability have been demonstrated when Zn(TFSI)2 is used in conjunction with Spiro-MeOTAD.

Chemical name:
Zinc(II) bis(trifluoromethanesulfonyl)imide

Alternative name:
Zn-TFSI2

Empirical Formula:
C4F12N2O8S4Zn

CAS number:
168106-25-0

Typical properties:
Mw = 625.65 g/mol

Specification:
Product specification DN-P17: Zn(TFSI)2

Reference:
• Energy Environ. Sci., 2018,11, 2985-2992, DOI: 10.1039/c8ee01500g
DN-P17
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DN-P20

F6-TCNNQ

Description:
F6-TCNNQ is a high electron affinity molecular dopant for hole-transport materials with a very wide range of applications stretching from perovskite solar cells to OPV, OLED and OFET. F6-TCNNQ is also a vacuum deposited molecular dopant that could be used together with hole transport-material TaTm for p-i-n perovskite solar cells (PCE > 20%)

Chemical name:
2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile

CAS number:
912482-15-6

Typical properties:
LUMO = -5.37 eV
HOMO = -9.32 eV
Mw = 362.19 g/mol

Reference:
• Cristina Momblona, et al., Energy & Environmental Science, 2016, DOI: 10.1039/c6ee02100j
• Fengyu Zhang, et al., Advanced Functional Materials, 2017, DOI: 10.1002/adfm.201703780
DN-P20


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