Hole transport materials and dopants

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

E_ox (DCM) = 0.64 V vs. NHE

Hole mobility = 1.5*10^-4 cm² V^-1 s^-1

λ_abs (DCM) = 365 nm, 307 nm (max)

M_W = 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

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

E_ox (DCM) = 0.65 V vs. NHE

Hole mobility = 1.9*10^-4 cm² V^-1 s^-1

λ_abs = 387 nm

M_W = 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

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

E_ox (DCM) = 0.65 V vs. NHE

Hole mobility = 5.5*10^-5 cm² V^-1 s^-1

λ_abs (PhMe) = 387 nm

M_W = 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

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:

E_ox (DCM) = 0.85 V vs. NHE

M_W = 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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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

λ_abs = 395 nm

M_n = 25 000 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

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

E_ox (DCM) = 0.62 V vs NHE

Hole mobility = 9.0*10^-4 S cm^-1

λ_abs (DCM) = 381 nm

M_W = 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

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

E_ox (DCM) = 0.73 V vs NHE

Hole mobility = 6.8*10^-4 S cm^-1

λ_abs = 402 nm

M_W = 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

• L. Vesce, et al., Energies 2021, 14(19), 6081; DOI: 10.3390/en14196081

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:

N^2',N^2',N⁵,N⁵,N^7',N^7',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

E_ox (DCM) = 0.67 V vs NHE

Hole mobility = 7.9*10^-5 cm² V^-1 s^-1

λ_abs (DCM) = 383 nm

M_W = 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

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:

λ_abs (on ITO glass) = 340 nm

M_W = 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

Additional information

This product is covered by patents of Helmholtz-Zentrum Berlin für Materialien und Energie GmbH in Germany and Kaunas University of Technology in Lithuania. Please contact us for further information.

Me-4PACz

Description:

DN-X10 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. Me-4PACz has shown the highest hole extraction efficiency of all tested SAMs and standard HTLs, with a with a certified power conversion efficiency of 29.15% for monolithic perovskite/silicon tandem solar cells.

Full name:

[4-(3,6-dimethyl-9H-carbazol-9-yl)butyl]phosphonic acid

Typical properties:

M_W = 331.35 g/mol

Recommended device concept:

• p-i-n Perovskite solar cells

References:

• Amran Al-Ashouri et al., Science, 2020, DOI: 10.1126/science.abd4016

Additional information

This product is covered by patents of Helmholtz-Zentrum Berlin für Materialien und Energie GmbH in Germany and Kaunas University of Technology in Lithuania. Please contact us for further information.

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,N^4'',N^4''-tetra([1,1'-biphenyl]-4-yl)-[1,1':4',1''-terphenyl]-4,4''-diamine

CAS number:

952431-34-4

Typical properties:

Purity: 99.9 %

HOMO = -5.40 eV

LUMO = -2.35 eV

Hole mobility = 4 * 10^-3 cm² V^-1 s^-1

M_W = 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

Br-2PACz

Description:

DN-X12 is a Self-Assembled Monolayer (SAM) hole conductor, that was used to obtain an impressive 18.4 % efficiency for organic solar cell (OPV), DOI: 10.1002/cssc.202100707. This is Dyenamo's first product that has been specifically developed for OPVs.

Full name:

[2-(3,6-dibromo-9H-carbazol-9-yl)ethyl]phosphonic acid

Typical properties:

HOMO = -6.01 eV

LUMO = -2.64 eV

Hole mobility = 5.4 * 10^-4 cm² V^-1 s^-1

M_W = 433.03 g/mol

Recommended device concept:

• organic solar cells (OPV)

References:

• Lin et al., ChemSusChem 2021, 14, 1-11 DOI: 10.1002/cssc.202100707

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

λ_abs.max = 388 nm

M_W = 1225.43 g/mol

Recommended device concept:

• n-i-p Perovskite solar cells

• p-i-n Perovskite solar cells

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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:

M_W = 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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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:

M_W = 1503.16 g/mol

Specification:

Product specification DN-P04: FK209

Reference:

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

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

M_w = 276.15 g/mol

Reference:

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

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:

M_w = 625.65 g/mol

Specification:

Product specification DN-P17: Zn(TFSI)₂

Reference:

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

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

M_w = 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