highly enhanced efficiency and stability all-small ... · studied by cyclic voltammetry (cva). cva...
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All-Small Molecule Solar Cells Based on Donor Molecular Optimization with
Highly Enhanced Efficiency and Stability
Jie Guo,a Haijun Bin,b Wei Wang,a Bingcai Chen,a Jing Guo,a Rui Sun,a Zhi–Guo
Zhang,b Xuechen Jiao,c* Yongfang Li,b* Jie Mina*
J. Guo, W. Wang, B. Chen, J. Guo, R. Sun, Prof. J. Min
The Insitute for Advanced Studies, Wuhan University, Wuhan 430072, China
E-mail: [email protected]
Dr. H. Bin, Prof. Z-G. Zhang, Prof. Y. Li
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Organic
Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
E-mail: [email protected]
Dr. X. Jiao,
Department of Materials Science and Engineering, Monash University, Victoria,
Australia
Australian Synchrotron, Clayton, VIC, Australia
E-mail: [email protected]
Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.This journal is © The Royal Society of Chemistry 2018
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1. Experimental Section
NN
N NN
N
S
S
S
S
ONC
O
ONC
O
C4H9
C2H5
C2H5
C4H9 F F F F
C8H17
C6H13
C8H17
C6H13
S S S S
S
S
SR
SR
NN
N
Br ONC
OC4H9
C2H5F F
C8H17
C6H13
S SSn Sn
S
S
S
S
S
S
SR
SR
21
Toluene, 110 oC
Pd(PPh3)4
BDT(TVT-SR)2(R=2-ethylhexyl)
Scheme S1. Synthetic route of the BDT(TVT-SR)2
Materials. IDIC was purchased from Solarmer Materials Inc. Solvents were dried and
distilled from appropriate drying agents prior to use. Monomer 1[1] and monomer 2[2]
were synthesized according to the procedures in the literatures, the synthetic route of
the small molecule donor BDT(TVT-SR)2 was shown in Scheme S1.
Synthesis of BDT(TVT-SR)2: Compound 1 (237 mg, 0.20 mmol) and Compound 2 (365
mg, 0.44 mmol) were dissolved in toluene (15 mL); after being flushed with argon for
5min, Pd(PPh3)4 (46 mg, 0.04 mmol) was added. Then the mixture was purged with
nitrogen for another 15 min, after which the reaction mixture was stirred at 110 oC in
dark under an nitrogen atmosphere overnight. After cooling to room temperature, the
reaction mixture was poured into water and extracted with dichloromethane. The
organic layer was further dried with anhydrous Mg2SO4 and filtered. The solevent was
evaporated under reduced pressure. The crude product was purified by column
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chromatography with hexane and dichloromethane (1:1) as eluent to afford a dark solid.
BDT(TVT-SR)2: (264 mg, 56% yield). 1H NMR (400 MHz, CDCl3, δ): 8.41-8.42 (d,
2H), 8.34-8.35 (d, 2H), 8.31 (s, 2H), 7.97-7.98 (d, 2H), 7.75 (s, 4H), 7.54-7.55 (d, 2H),
7.40-7.41 (d, 2H) , 7.37 (m, 4H), 7.29-7.30 (d, 2H), 7.02-7.03 (d, 2H), 4.79-4.80 (d,
4H), 4.25-4.26 (d, 4H), 2.98-2.99 (d, 4H), 2.03-2.06(m, 4H), 1.60-1.63(m, 2H), 1.40-
1.55(m, 8H), 1.26-1.38(m, 72H), 0.84-1.05 (m, 36H). MALDI-TOF MS: Calcd. for
C130H158F4N8O4S12 m/z = 2355.90; Found 2351.0. Elemental analysis: Calcd for
C130H158F4N8O4S12 (%): C, 66.23; H, 6.76; N, 4.75. Found (%):C, 66.35; H,
6.72;N, 4.76.
Material characterization. 1H NMR spectra were measured on a Bruker DMX-400
spectrometer with d-chloroform as the solvent and trimethylsilane as the internal
reference. Absorption profiles were recorded with a Perkin Elmer Lambda-35
absorption spectrometer from 350 nm to 1100 nm. Electrochemical properties were
studied by cyclic voltammetry (CVA). CVA was performed on a CS350H
electrochemcial workstation with a three-electrode system in a 0.1 M [Bu4N]PF6
acetonitrile solution at a scan rate of 20 mVs-1. Glassy carbon disc coated with sample
film was used as the working electrode. A Pt wire was used as the counter electrode
and Ag/AgCl was used as the reference electrode. The HOMO and LUMO levels are
calculated from the onset potentials of oxidation and reduction with respect to the
energy level of ferrocene/ferrocenium couple, which was taken as -4.8 eV below the
vacuum level.
Fabrication and characterization of the OSCs. All the devices were fabricated in the
normal architecture. Photovoltaic devices were fabricated by doctor-blading on indium
tin oxide (ITO)-covered glass substrates (from Osram). These substrates were cleaned
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in toluene, water, acetone, and isopropyl alcohol. After drying, the substrates were
bladed with 40 nm PEDOT:PSS (HC Starck, PEDOT PH-4083). The photovoltaic
layers was spin-coated in a glovebox from a solution of BDT(TVT-SR)2:IDIC with 12
mg/mL in chloroform. After that, the layers were annealed at 110 oC for 10 min for the
devices with thermal annealing treatment. A perylene diimide functionalized with
amino N-oxide (PDINO) layer via a solution concentration of 1.0 mg/mL was deposited
the top of active layer. Finally, top aluminum electrode of 100 nm thickness was
evaporated in vacuum onto the cathode buffer layer at a pressure of 5×10-6 mbar. The
typical active area of the investigated devices was 4 mm2. The current-voltage
characteristics of the solar cells were measured by a Keithley 2400 source meter unit
under AM 1.5G irradiation from a solar simulator (Enlitech model SS-F5-3A). Solar
simulator illumination intensity was determined at 100 mW cm-2 using a monocrystal
silicon reference cell with KG5 filter. Short circuit currents under AM 1.5G conditions
were estimated from the spectral response and convolution with the solar spectrum. The
external quantum efficiency was measured by a Solar Cell Spectral Response
Measurement System QE-R3011(Enli Technology Co., Ltd.).
AFM measurements were performed with a Nanosurf Easy Scan 2 in contact mode.
Single carrier devices were fabricated and the dark current-voltage characteristics
measured and analyzed in the space charge limited (SCL) regime following the
references. The structure of hole only devices was Glass/ITO/PEDOT:PSS/Active
layer/MoO3/Ag (100 nm). For the electron only devices, the structure was
Glass/ITO/ZnO/Active layer/Ca (15 m)/Ag (80 nm), where both Ca and Ag were
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evaporated. The reported mobility data are average values over the two cells of each
sample at a given film composition.
Fiugre S1. 1H NMR spectrum of compound 1a in CDCl3.
100 200 300 400 50080
85
90
95
100
Temperature(C)
Wei
ght(%
)
BDT(TVT-SR)2
350C
Figure S2. TGA plots of BDT(TVT-SR)2 with a heating rate of 10 ºC min-1 in air.
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50 100 150 200 250 300
Spec
ific
heat
flow
(W/g
)
Temperature(C)
1st heating 1st cooling 2nd heating 2nd cooling
Figure S3. DSC thermograms of the BDT(TVT-SR)2: 1st heating, 1st cooling, 2nd heating and 2nd cooling.
Table S1. Summary of optical properties and electronic energy levels of BDT(TVT-SR)2.
Solution
λmaxa
(nm)
Film
λmaxb
(nm)
M-1
cm-1
Egopt,
c
(eV)
HOMOd
(eV)
LUMOd
(eV)
Egcv
(eV)
HOMOe
(eV)
LUMOe
(eV)
519558,
602
8.16 ×
1041.82 -5.11 -3.02 2.10 -5.33 -3.18
aMeasured in chloroform solution. bCast from chloroform solution. cBandgap estimated from the onset wavelength (λedge) of the optical absorption: Eg
opt = 1240/λedge. dMeasured by electrochemical cyclic voltammetry. eObtained by DFT calculation.
300 400 500 600 700 8000.0
0.2
0.4
0.6
0.8
1.0 H11 (film) BDT(TVT-SR)2
Norm
alize
d Ab
sorb
ance
(a.u
.)
Wavelength (nm)300 400 500 600 700 800
0.0
0.2
0.4
0.6
0.8
10
5 M-
cm-1
Wavelength (nm)
H11 (solu.) BDT(TVT-SR)2
(a) (b)
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Figure S4. UV-vis absorption spectra of H11 and BDT(TVT-SR)2 in chloroform solutions (a) and in thin films (b).
-1.5 -1.0 -0.5 0.0 0.5 1.0 1.5
Cur
rent
(a.u
.)
Potential (V)
Fc/Fc+
BDT(TVT-SR)2
Figure S5. Cyclic voltammogram of BDT(TVT-SR)2 polymer film on a platinum electrode measured in 0.1 mol L−1 Bu4NPF6 acetonitrile solutions at a scan rate of 20 mV s−1, the inser figure (black line) shows the ferrocene/ferrocenium (Fc/Fc+) couple used as an internal reference.
55.80
51.70
Top view Side view
H11
BDT(TVT-SR)2
Figure S6. Molecular geometry of the small molecule donor materials calculated by DFT/B3LYP/6-31G(d, p) with methyl groups in replacing alkyl substituents to simplify the calculations.
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NN
N NN
N
S
S
S
S
ONC
O
ONC
O F F F FS S S S
NN
N NN
N
S
S
S
S
ONC
O
ONC
O F F F FS S S S
S
S
S
S
LUMO = -2.98 eV LUMO = -3.02 eV
HOMO = -5.08 eV HOMO = -5.11 eV
H11 BDT(TVT-SR)2
Figure S7. LUMO and HOMO energy levels of the small molecules calculated by DFT/B3LYP/6-31G(d, p) with methyl groups in replacing alkyl substituents to simplify the calculations.
5 10 15 20 25 300
500
1000
1500
2000
Inte
nsity
(CPS
)
2-theta (deg)
BDT(TVT-SR)2 H11
Figure S8. XRD patterns of BDT(TVT-SR)2 and H11 films spin-coated from CHCl3 on silicon wafer.
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0 1 2 3 4 5 610-2
10-1
100
101
102
103
104
Hole Only Device:
BDT(TVT-SR)2
( nm; h = -cmV-s-) H11
( nm; h = -cmV-s-)
J (A
/m2 )
Vin (V)
Figure S9. The dark J–V characteristics of pure BDT(TVT-SR)2 and H11 films based hole-only devices, respectively. Solid lines are the fitting lines of the data.
-0.2 0.0 0.2 0.4 0.6 0.8 1.0 1.2
-16-14-12-10
-8-6-4-202
Cur
rent
Den
sity
(mA
cm
-2)
Voltage (V)
as cast 70 oC 90 oC 110 oC 120 oC 140 oC
Figure S10. J-V curves of the OSCs based on BDT(TVT-SR)2:IDIC (2:1, wt%) under different annealing temperature conditions.
Table S2. Photovoltaic parameters of the OSCs based on BDTT-S-TR:IDIC (2:1, wt%) under different annealing temperature conditions.
Conditions Annealing[oC]
Voc
[V]Jsc
[mA/cm²]FF[%]
PCE[%]
01.01
(1.01 ± 0.003)10.22
(9.54 ± 0.377)54.63
(53.03 ± 0.556)5.64
(5.18 ± 0.231)
701.01
(1.00 ± 0.012)11.32
(10.13 ± 1.004)58.57
(56.32 ± 1.032)6.70
(5.78 ± 0.539)Temp.
(D:A; 2:1)
900.99
(0.99 ± 0.004)13.91
(12.90 ± 0.432)64.37
(65.31 ± 1.020)8.86
(8.47 ± 0.218)
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1100.98
(0.98 ± 0.004)15.92
(15.56 ± 0.251)71.15
(69.94 ± 1.104)11.10
(10.60 ± 0.221)
1200.96
(0.97 ± 0.004)14.81
(14.52 ± 0.216)65.81
(64.58 ± 1.362)9.36
(9.07 ± 0.196)
1400.95
(0.93 ± 0.015)14.66
(14.46 ± 0.306)60.42
(56.77 ± 2.383)8.41
(7.63 ± 0.360)
-0.2 0.0 0.2 0.4 0.6 0.8 1.0 1.2
-16-14-12-10
-8-6-4-202
Cur
rent
Den
sity
(mA
cm
-2)
Voltage (V)
D:A; w/w 1:1 1.5:1 2:1 2.5:1 3:1
Figure S11. J-V curves of the annealed OSCs based on BDT(TVT-SR)2:IDIC with different blend D:A weight ratios. All of blends was treated by thermal annealing at 110 oC for 10 min.
Table S3. Photovoltaic parameters of the OSCs based on BDT(TVT-SR)2:IDIC with different blend D:A weight ratios, under the illumination of AM1.5G at 100 mW cm-2.
Conditions D:A, w/w Voc
[V]Jsc
[mA/cm²]FF[%]
PCE[%]
1:10.96
(0.95 ± 0.002)14.02
(13.14 ± 0.475)60.36
(58.83 ± 1.026)8.12
(8.02 ± 0.254)
1.5:10.98
(0.97 ± 0.004)15.03
(14.46 ± 0.229)67.57
(66.15 ± 0.757)9.95
(9.57 ± 0.485)
2:10.98
(0.98 ± 0.004)15.92
(15.56 ± 0.251)71.15
(69.94 ± 1.104)11.10
(10.60 ± 0.228)
2.5:10.98
(0.98 ± 0.008)14.82
(14.05 ± 0.389)65.70
(64.35 ± 1.327)9.54
(9.34 ± 0.306)
Ratio(Blends: 10min
@110 oC)
3:10.99
(0.98 ± 0.006)12.16
(11.51 ± 0.466)57.78
(56.32 ± 1.063)6.96
(6.53 ± 0.417)
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-0.2 0.0 0.2 0.4 0.6 0.8 1.0 1.2
-16-14-12-10
-8-6-4-202
Cur
rent
Den
sity
(mA
cm
-2)
Voltage (V)
75 nm 95 nm 110 nm 140 nm 180 nm
Figure S12. J-V curves of the annealed OSCs based on BDT(TVT-SR)2:IDIC with different photoactive layer thickness. The blends was treated by thermal annealing at 110 oC for 10 min.
Table S4. Photovoltaic parameters of the OSCs based on BDT(TVT-SR)2:IDIC with different photoactive layer thickness, under one sun illumination.
Conditions Thickness[nm]
Voc
[V]Jsc
[mA/cm²]FF[%]
PCE[%]
750.98
(0.98 ± 0.002)15.27
(14.95 ± 0.245)66.63
(65.12 ± 1.214)9.97
(9.52 ± 0.461)
950.98
(0.98 ± 0.002)15.51
(15.46 ± 0.187)67.73
(65.15 ± 1.489)10.29
(9.88 ± 0.417)
1100.98
(0.98 ± 0.004)15.92
(15.56 ± 0.251)71.15
(69.94 ± 1.104)11.10
(10.60 ± 0.228)
1400.97
(0.97 ± 0.006)14.87
(14.12 ± 0.395)63.19
(61.35 ± 1.319)9.15
(8.54 ± 0.325)
Thickness(D:A: 2:1;
10min @110 oC)
1800.95
(0.95 ± 0.006)13.45
(12.68 ± 0.517)56.96
(53.32 ± 1.798)7.28
(6.71 ± 0.515)
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-0.2 0.0 0.2 0.4 0.6 0.8 1.0 1.2
-16-14-12-10
-8-6-4-202
Cur
rent
Den
sity
(mA
cm
-2)
Voltage (V)
CF-WO CF-W CB-WO CB-W ODCB-WO ODCB-W
Figure S13. J-V curves of the OSCs based on BDT(TVT-SR)2:IDIC (2:1, wt%) using different solvents wihtout and with TA treatments.
Table S5. Photovoltaic parameters of the OSCs based on BDT(TVT-SR)2:IDIC (2:1, wt%) using different solvents without and with TA treatments (110 oC).
Conditions TA treatment
Voc
[V]Jsc
[mA/cm²]FF[%]
PCE[%]
Without 1.01
(1.01 ± 0.003)10.22
(9.54 ± 0.377)54.63
(53.03 ± 0.556)5.64
(5.18 ± 0.231)Chloroform (CF)
With0.98
(0.98 ± 0.004)15.92
(15.56 ± 0.251)71.15
(69.94 ± 1.104)11.10
(10.60 ± 0.228)
Without 1.00
(1.00 ± 0.005)9.65
(9.10 ± 0.432)52.71
(47.31 ± 2.120)5.09
(4.39 ± 0.314)Chlorobenzene (CB)
With0.97
(0.96 ± 0.004)13.83
(12.88 ± 0.313)63.54
(57.85 ± 3.104)8.52
(7.90 ± 0.312)
Without 1.01
(1.00 ± 0.004)8.95
(8.10 ± 0.356)49.32
(44.39 ± 3.398)4.46
(3.25 ± 0.413)Dichlorobe
nzene (ODCB) With
0.97(0.96 ± 0.004)
12.87(11.89 ± 0.417)
57.58(52.63 ± 3.566)
7.19(6.84 ± 0.376)
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(b)(a)
1 μm 1 μm
Figure S14. AFM top images (size: 5 5 μm2) of BDT(TVT-SR)2:IDIC (a) and ×
H11:IDIC (b) blends.
100 101 102
50
60
70
as cast TA treatment
FF (%
)
Light Intensity (mW cm-2)100 101 102
0.8
0.85
0.9
0.95
1
1.05
1.04 kT/q
as cast TA treatmentO
pen
Circ
uit V
olta
ge (V
)
Light Intensity (mW cm-2)
1.29 kT/q
(a) (b)
Figure S15. The measured (a)FF and (b)Voc of un-annealed and annealed devices as a function of light intensity (symbols), together with linear fits to the Voc data (solid lines).
1 2 3 4 5 610-1
100
101
102
103
104
Curr
ent d
ensi
ty (m
A/cm
*cm
)
Voltage (V)
WO (5.7510-5 cm2V-1s-1) TA (1.4810-4 cm2V-1s-1) H11_TA (8.6510-5 cm2V-1s-1)
Fitting curves
1 2 3 4 5 6
101
102
103
104
Curr
ent d
ensi
ty (m
A/cm
*cm
)
Voltage (V)
WO (1.3410-4 cm2V-1s-1) TA (1.9510-4 cm2V-1s-1) H11_TA (1.2110-4 cm2V-1s-1)
Fitting curves
(a) (b)
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Figure S16. J-V characteristics in the dark for (a) hole-only devices and (b) electron-only devices of BDT(TVT-SR)2:IDIC blends with and withtout TA treatment as well as the optimized H11:IDIC blends.
500 nm 500 nm
(a) (b)
Figure S17. TEM image results of BDT(TVT-SR)2:IDIC blend films (a) without and
(b) with TA treatment.
0.325 0.55 0.7751
3.25
0.1
1
10
Inte
nsity
(a. u
.)
2-theta (deg)
as cast TA treatment
Figure S18. Specular XRD results for BDT(TVT-SR)2:IDIC blend films without and
with TA treatment.
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0 50 100 150 2000.6
0.7
0.8
0.9
1.0
1.1
Voc Jsc FF PCE
Norm
alize
d De
vice
Par
amet
ers
(a.u
.)
Aging time (hours)0 50 100 150 200
0.6
0.7
0.8
0.9
1.0
1.1
Voc Jsc FF PCE
Norm
alize
d De
vice
Par
amet
ers
(a.u
.)
Aging time (hours)
(a) (b)
Figure S19. Variation of normalized average device photovoltaic parameters over 200 h, one sun illumination for the encapsulated devices based on (a) BDT(TVT-SR)2 blend and (b) H11 blend.
0 20 40 60 80 100
0.4
0.6
0.8
1.0
BDT(TVT-SR)2 H11
Norm
alize
d J s
c
Annealing Time (h)0 20 40 60 80 100
0.7
0.8
0.9
1.0
Norm
alize
d V o
c
Annealing Time (h)
BDT(TVT-SR)2 H11
0 20 40 60 80 1000.6
0.8
1.0
BDT(TVT-SR)2 H11
Norm
alize
d FF
(%)
Annealing Time (h)0 20 40 60 80 100
0.4
0.6
0.8
1.0
Norm
alize
d PC
E
Annealing Time (h)
BDT(TVT-SR)2 H11
(a) (b)
(c) (d)
Figure S20. Changes of (a) normalized Voc, (b) normalized Jsc, (c) normalized FF and (d) normalized PCE of BDT(TVT-SR)2:IDIC, and H11:IDIC based devices as a function of annealing time at 80 oC.
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16
300 400 500 600 700 8000.0
0.1
0.2
0.3
0.4
0.5
0.6
Abso
rban
ce
Wavelength (nm)
0 h 2 h 24 h
400 500 600 700 8000.0
0.1
0.2
0.3
0.4
0.5
0.6
Abso
rban
ce
Wavelength (nm)
0 h 2 h 24 h
(a) (b)
Figure S21. UV-vis absorption of BDT(TVT-SR)2:IDIC (a) and H11:IDIC (b) blends as a function of annealing time at 120 oC.
(d) (e) (f)
(a) (b) (c)0h; RMS 3.43 nm 2h; RMS 3.47 nm 24h; RMS 3.70 nm
0h; RMS 3.45 nm 2h; RMS 3.69 nm 24h; RMS 5.71 nm
1 μm 1 μm 1 μm
1 μm 1 μm 1 μm
Figure S22. AFM top images of morphological evolution of BDT(TVT-SR)2:IDIC (top) and H11:IDIC (bottom) blends without (a, d) and with 2hours (b, e) and 24 hours (c, f) thermal annealing treatmetns. The scanning area is 5×5 mm2 for all images.
References
[1] H. Yao, H. Zhang, L. Ye, W. Zhao, S. Zhang, J. Hou, Macromolecules, 2015, 48, 3493-3499.
[2] H. Bin, Y. Yang, Z.-G. Zhang, L. Ye, M. Ghasemi, S. Chen, Y. Zhang, C. Zhang, C. Sun, L. Xue, C. Yang, H. Ade, Y. Li, J. Am. Chem. Soc., 2017, 139, 5085-5094.