Cost Flexibility Tunability
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CostFlexibilityTunability
TTF 1973 Poly(acetylene) 1977
(opto)electronic devices:FETs, LEDs, Solar cells
Sensors, electrodes
energy storage
antistaticsÉlectromagnétism
protection
RéversibilitySemi-conductor
conductor
Marseille 2009
Marseille 2009
Marseille 2009 Source: OCDE
Source: UN
SUN3,900,000 EJ theory
50,000 EJ technically possible
Biomasse2,900 EJ theory
300 EJ technically possible
Hydroelectricity40,000 EJ theory
10,000 EJ technically possible
Geothermic140,000,000 EJ theory
5,000 EJ technically possible
Wind5,800 EJ theory
300 EJ technically possible
Oceans7,400 EJ theory
…In 1h, 440EJ on Earth1 year of energy consumption…
ITO
Metal
Pedot-pss
Active layer
Injection layer
SEMI-CONDUCTOR
S
N
S
S
CN
CN
NCCN
CN
NC
CONJUGATED POLYMERS
Marseille 2009
électrode
Absorption +–
Dissociation
Transport
+
–
+
–––
++
Collection
électrode
Diffusion
+–
Marseille 2009
électrode
+–
Dissociation
+
–
+
–––
++électrode
+–
E
D A+. -.
Photoinduced electron transfer : electricity …
8Marseille 2009
électrode
électrode
+–
+–
+–
+–
électrode
+– +
–
+
–––
++électrode
+–
Bilayer (BL SC) Bulk heterojunction (BHJ SC)
Marseille 2009
Current density
Open circuit voltage
Fill factor
PV yield
Solar light
harvesting
Stability
Mobility
Morphology
Interface between
the domains
HOMO-LUMO gap
HOMO level
Geometry of
compounds
Nature of compounds
(molecules or
polymers )
Organisation
Depositionmethod
StructureTreatmentadditives
ITO
Verre
PEDOT-PSS
Acceptor
Metal
– +–
Donor
ITO
Glass
PEDOT-PSS
Metal
– +–
BL SC
BHJ SC
Marseille 2009
Bulk heterojunction solar
cells
Low band gap or regioregular
isotropic polymersITO
Verre
PEDOT-PSS
Acceptor
Metal
– +–
Donor
ITO
Glass
PEDOT-PSS
Metal
– +–
BL SC
BHJ SC
Hou et al, Nature Materials, 3, 2009, 649Marseille 2009
Hou et al, Nature Materials, 3, 2009, 649Marseille 2009
Longueur d'onde (nm)
400 600 800 1000 1200 1400
Irra
dian
ce s
pect
rale
(W
.m-2
.nm
-1)
0.0
0.2
0.4
0.6
0.8
1.0
1.2
1.4
1.6
1.8
Abs
orba
nce
Si (1,1 eV)
P3HT 1,9 eV
P3HT
HOMO
Accepteur
HOMO
LUMO
∆E ∝ VOC
vide0
Energy (eV)
-4.70
-5.27
LUMO
Air unstability
-3.00
D-A polymer
Moove the homo level in
the air stability zone
Increase VOC
Improve light harvesting
(P3HT/C60 : η0.15%)
Solid states
Polymer
Jsc (mA.cm -
2)2.06
Voc (V) 0.75
FF (%) 25
ηηηη (%) 0.38
S n
P3HT
Bricaud et al. Synth. Metals (2009), in press
651nm
Marseille 2009
Marseille 2009
Bulk heterojunction solar
cells
Low band gap or regioregular
isotropic polymers
ITO
Verre
PEDOT-PSS
Acceptor
Metal
– +–
Donor
ITO
Glass
PEDOT-PSS
Metal
– +–
BL SC
BHJ SC
Reproductibility (regioregularity,
polydispersity)
Pollution (organometallic
catalysts)
Cost (catalysts, purification)
Marseille 2009
3D MOLECULAR derivatives may lead to
Good reproducibilityEasy purification
Isotropic materialsGood processabilityHigh solubility
Si
SiO2
Semiconducting material
Au Au
drain source
gate
W
L
ITO
Verre
PEDOT-PSS
Acceptor
Metal
– +–
Donor
Marseille 2009
Leriche et al. Org. Biomol. Chem. (2008), 6, 3202
Cravino et al. Chem. Mater (2006), 2584
Roquet et al. J. Mater. Chem. (2006), 3040
Karpe et al. Adv. Funct. Mater.. (2007), 17, 7, 1163
Sherf and Co. Bauerle and Co.
For recent reviews on Three-Dimensional Organic Se miconductors see Roncali et al. Adv. Mater. (2007), 2045Roncali, J. ” Molecular Bulk Heterojunctions: An Emerging Approac h to Organic Solar Cells” . Acc. Chem. Res (2009) in press
SiS
S SS
S
S
SS
S
S
S
S
C6H13
C6H13
C6H13
C6H13
N
S
S
S
S
S
S
S
S
S
C6H13
C6H13
C6H13
PS
S SC6H13
S
S
S
C6H13
S
S
S
C6H13
O
S
S S
S S
S
S
S
S
S
S
S
SBu
BuS
BuSSBu
Marseille 2009
-1.0 -0.5 0.0 0.5 1.0-3.5
-3.0
-2.5
-2.0
-1.5
-1.0
-0.5
0.0
0.5
Den
sité
de
cour
ant (
mA
/cm
²)
Tension (V)
Jsc=1.13mA/cm2
Voc=0.85V
η=0.30%
FF=0.24
λmax=390nm
ITO
Glass
PEDOT-PSS
Metal
– +–
Donor
Acceptor
Better than linear analogues
Fragile C-Si bond
moderate solar light
harvestingRoquet et al. J. Mater. Chem. (2006),
3040
SiS
S SS
S
S
SS
S
S
S
S
C6H13
C6H13
C6H13
C6H13
Marseille 2009
Are these systems incorporable in solar cells ? YES
What about solar light harvesting, hole mobility an d stability ?
TO BE IMPROVED
!!!For Reviews on TPA derivatives see: Shirota, Y. J. Mater. Chem. 2000, 10, 1. Shirota, Y. J. Mater. C hem.
2005, 15, 75
S
SR
R S
RR
S
S
S
R R
R
RN
S
S
S
Marseille 2009
SBr
S Br
S
S
Br
Br
SBu3Sn
Pd(PPh3)4
S
Br
Br
S
S
S
S
S
NBS
CHCl3/AcOH
Zn
Reflux
Marseille 2009
SBr
S Br
S
S
Br
Br
S
S
S
S
1 tridimensionnal molecule
1 cruciform quaterthiophene
4 independant systems
S
S
R
R
S
S
R
R
Karpe et al. Adv. Funct. Mater. (2007), 17, 7, 1163
Marseille 2009
S
S
N
SS
S
S
S
S
N
S
S
N S
S
N
CN
CN
CNNC
NC
NC
NCCN
S
S
N
SS
S
S
S
S
N
S
S
N S
S
N
S
S
N
SS
S
S
S
S
N
S
S
N S
S
N
O
O
O
O
H
H
H
H
DMF
41 % 55 %
MalonotrileN(Et)3
POCl3
dichloroEthane
S S
N
SnMe3
SS
S
S
Br
Br
Br
Br
+
5% Pd(PPh3)
toluene
35 %
Marseille 2009
410nm 526nm
≈0.75V≈ 1V
εεεε= 111000 L.cm -1.mol -1
εεεε= 72900 L.cm -1.mol -1
Marseille 2009
ITO
Glass
PEDOT-PSS
Metal
– +–
Yield (%) = 0.66
Voc (V) = 0.736Jsc (mA/cm²) = -3.04Fill Factor = 29.7 %
Yield (%) = 0.2
Voc (V) = 0.887Jsc (mA/cm²) = -1.19Fill Factor = 19 %
Marseille 2009
Are these systems incorporable in solar cells ? YES
What about solar light harvesting, hole mobility an d stability ?
TO BE IMPROVED
!!!For Reviews on TPA derivatives see: Shirota, Y. J. Mater. Chem. 2000, 10, 1. Shirota, Y. J. Mater. C hem.
2005, 15, 75
S
SR
R S
RR
S
S
S
R R
R
RN
S
S
S
Marseille 2009
µµµµ=2.10-2 cm2.V-1.s-1
µµµµ=9.10-5 cm2.V-1.s-1
Cravino et al. Chem. Mater., (2006), 18, 2584
Cremer et al., Chem. Mater., (2007), 19, 4155Li et al. Synth. Metals, (2008), 158, 150
Si
SiO2
Semiconducting material
Au Au
drain source
gate
W
L
N
S
S
S
S
S
S
S
S
S
C6H13
C6H13
C6H13
N
S
S
S
S
S
S
Marseille 2009
N
S
S
S
S
SR
R
SS
S
S
R
R
R
R
N
S
S
S
S
SR
R
S
S
R
R
N
S
S
S
S
SR
R
N
S
SR
R
N
S
SR
R
N
S
SR
R
S
S
R
R
SS
RR
SS
RR
Leriche et al. New. J. Chem., (2009), 33, 801Marseille 2009
µµµµ (cm2.v-1.s-1) Ion/off
1.2 10-2 50
5.0 10-2 15
4.0 10-2 350
8.0 10-2 50000
S
SS
S
Mobilities all higher than 10 -2
cm2.v-1.s-1
Non homogeneous I on/off ratio !!!
(V/SCE)0.45
0.32
0.72
1.00O. Alévêque et al. J. Mater. Chem. 2009
SiSiO2
Au Au
drain source
gate
W
L
Marseille 2009
Higher I on/off ratio
Higher stability in ambiant
conditions
Better mobility
Vg=0 to -50V
Marseille 2009 O. Alévêque et al. J. Mater. Chem. 2009
T. Breton (CIMA), R. Filmon, R. Mallet (service commun de microscopie de l’Université d’Angers)
Similar morphologies
Larger grain size for the meta isomer
SS
SS
Marseille 2009
Alévêque et al. Solar En. Mat. and Solar cells, (2008) , 92, 1170
Solid state
In CH2Cl2
µµµµ=3.2.10-4 cm2.V-1.s-1
Marseille 2009
ITO
Verre
PEDOT-PSS
C60
Metal
– +–
TPATTF
Max EQE 6%Voc = 0.4 VJsc = 0.87 mA cm -2
FF = 0.32η η η η = = = = 0.11%
N. Martin et al. Acc. Chem. Res., (2007), 40, 1015: 0.04% on a single layered dual material cellP. J. Skabara et al., J. Phys. Chem. B., (2006), 11 0, 3140: 0.14% wirh a BHJ incorporating a TTF containing polymer
Alévêque et al. Solar En. Mat. and Solar cells, (2008) , 92, 1170Marseille 2009
Polarity
Polarisability
DissymetrizationN
S
CN
NC
S
S
S
R
Marseille 2009
Nature and number of electron accepting moieties
Marseille 2009
Nature of electron accepting moieties
DMF, POCl3BrN
3 Pd(PPh3)4
S SnBu3
3SN
S
N
SOHC
S
CHO
CHO
S
N
S
S
S
N
S
S
S
N
S
S
CN
CN
NCCN
CN
NC
NN
N
N
N
N
O
O
O
O
O
O
O
O
S
O
O
S
O
O
S90% 1% 85%
90%85%
NEt3
CN
CN
O
ON
N
O
O
Sou
Marseille 2009
S
N
S
S
S
N
S
S
CN
CN
NCCN
CN
NC
50%NC
NC CN
CN
NC
NC
CN
S
N
S
S
CN
CN
CN
NC
NC
CN
S
N
S
S
CN
CN
NC
29%
Traces
number of electron accepting moieties
Marseille 2009
85%
S
N
S
S
CN
CN
NCCN
CN
NC
1) NaCN
2) H+, Pb(OAc)4
number of electron accepting moieties
S
N
S
S
S
N
S
S
CN
CN
NCCN
CN
NC
50%NC
NC CN
CN
NC
NC
CN
S
N
S
S
CN
CN
CN
NC
NC
CN
S
N
S
S
CN
CN
NC
29%
Traces
Marseille 2009
ICT band
High oxidation
potential
redox ampholyte
N
S
S
S
CN
CNNC
Marseille 2009
CH2Cl2, TBAPF6 0.1M
0.88V
1.00V
1.19V
P. Leriche et al. , J . Org. Chem., (2007), 72, 83 32
-0.56V
-0.63V
-0.64V
N
S
S
S
CN
CNNC
ICT band
High oxidation
potential
redox ampholyte
Band gap controlMarseille 2009
CN
CN
O
O
N
N
O
O
S
528nm 613nm
P. Leriche et al. , J . Org. Chem., (2007), 72, 83 32Marseille 2009
ITO~-4.5
Baytron
C60 -6.3
C60 -4.1Al ~-4.2
Eox ferrocene = 4.15eV
-6.0-6.1
-5.8
-6.0
-3.7 -3.8
-4.0
-4.3
eV
CN
CN
O
O
N
N
O
O
S
Marseille 2009
NC
S
NCN
S
SNC
NC
NC
CN
S
N
S
S
S
CN
NC
NCCN
S
S
N
S
S
S
NCCN
Marseille 2009
S
S
N
S
S
S
NCCN
NC
S
NCN
S
SNC
NC
NC
CN
S
N
S
S
S
CN
NC
NCCN
1.09V
0.90V
0.73V
0.65V
Marseille 2009
S
S
N
S
S
S
NCCN
NC
S
NCN
S
SNC
NC
NC
CN
S
N
S
S
S
CN
NC
NCCN
Max EQE 28%Voc = 1.15 VJsc = 4.6 mA cm -2
FF = 0.28ηηηη = 1.85%
Max EQE 28%VOC=0,89VJ=3,65 mA.cm -2
FF=0,36η η η η =1,17%
Max EQE 33%VOC=0,72VJ=1,97 mA.cm -2
FF=0,34ηηηη=0,49%
Max EQE 20%%VOC=0,6VJ=2,43 mA.cm -2
FF=0,28R=0,41%
C60
ITO
TPA derivativeC60
AlLiF
Roquet et al., J. Am. Chem. Soc., (2006), 128, 3459Cravino et al., Adv. Mater., (2006), 18, 3033
S
S
N
S
S
S
NCCN
NC
S
NCN
S
SNC
NC
NC
CN
S
N
S
S
S
CN
NC
NCCN
Solar light harvesting
Oxidation potential / V OC link : high
VOC
High stability of films in ambiant Marseille 2009
Max EQE 32%Voc = 0.66 VJsc = 4.1 mA cm -2
FF = 0.30η η η η = = = = 0.81%
λmax=419nm
λICT=536nm
ITO
Glass
PEDOT-PSS
Metal
– +–
Donor
Acceptor
Roquet et al., J. Am. Chem. Soc., (2006), 128, 3459Marseille 2009
Polarizability
Assymetrizatio
nE. Ripaud, in progress
N
S
S
S
NC
NC
CN
NC
NC
CN
Marseille 2009
Commercialyavailable
Marseille 2009
NC
S
NCN
S
SNC
NC
NC
CN
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