OPV Workshop September 20, Materials for Polymer Solar Cells: Achievements and Challenges. Wei You

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1 OPV Workshop September 20, 2012 Materials for Polymer Solar Cells: Achievements and Challenges Wei You Department of Chemistry University of North Carolina at Chapel Hill 1

2 Bulk Heterojunction Solar Cell Cathode (e.g.,ca/al) Active Layer Interfacial Layer Anode (e.g.,ito) 2

3 Outline I. Past: what we have accomplished? Rational design of conjugated polymers (or molecular engineering) a) Backbone b) Side chains c) Substituents II Current: where we stand now? a) F impact b) Orientation at the D/A interface III Future: what we could do or should do? a) J sc b) V oc c) Stability 3

4 Outline I. Past: what we have accomplished? Rational design of conjugated polymers (or molecular engineering) a) Backbone b) Side chains c) Substituents II Current: where we stand now? a) F impact b) Orientation at the D/A interface III Future: what we could do or should do? a) J sc b) V oc c) Stability 4

5 Side chains Backbone repeating unit Substituent 5

6 a) Backbone: Weak Donor Strong Acceptor b) Side Chains Position Shape and size c) Substituents The curious case of fluorine 6

7 Review by Thompson et al. Chem. Commun., 2011, 47, DOI: /c0cc04020g weak donor strong acceptor Zhou, Yang, Stoneking & You, ACS Appl. Mater. Interfaces 2010, 2,

8 Polymer HOM O (ev) LUMO (ev) E gap (opt) V oc (V) J sc (ma/cm 2 ) FF η % Refer ACIE 2011, 50, 2995.* JACS 2011, 133, 4625.* ACIE 2010, 49, ACIE 2010, 49, 7992l *among "the hottest research of 2011 by Thomson Reuters

9 9

10 M n = 30 kg/mol M w = 92 kg/mol M n = 37 kg/mol M w = 84 kg/mol M n = 27 kg/mol M w = 54 kg/mol Zhou, Yang, Liu & You, Macromolecules 2010, 43,

11 Current Density (ma/cm 2 ) PBDT-DTBT PBDT-DTsolBT PBDT-3DTBT PBDT-4DTBT PBDT-4DTBT (with 3% additive) Voltage (V) Polymer PBDT-4DTBT (3% diiodooctane) Polymer: PCBM Thicknes s (nm) V oc (V) J sc (ma/cm 2 ) FF η (%) Mobility (cm 2 /V s) 1: % 2.17% PBDT-4DTBT 1: % 1.83% PBDT-3DTBT 1: % 0.21% PBDT-DTsolBT 1: % 0.01% PBDT-DTBT 1: % 0.72% PBDT-BT 1: % 0.60%

12 J (ma/cm 2 ) 6 0 C10,6-C8 C10,6-C6,2 C8-C8 C8-C12 C8-C6,2 C6,2-C6, Voltage (V) Long branched side chains weaken intermolecular interactions, leading to an increased V oc but a much lower J sc Yang, Zhou & You, J. Phys. Chem. C 2010, 114,

13 Polymer C10,6-C8 C10,6-C6,2 C8-C8 C8-C12 C8-C6,2 C6,2-C6,2 J s J s (ma/cm 2 ) 1.80 E E E E E E 03 J so (ma/cm 2 ) EDA Jso exp 2 nkt n nkt q ln J SC J SO HOMO (ev) E DA 2q V oc (V) Cal V oc (V) Exp J sc (ma/cm 2 ) Cal J sc (ma/cm 2 ) Exp V oc nkt Jsc E ln q Jso 2q DA 13

14 5.0% 4.3% 7.2% 7.1% Zhou, Yang, Stuart, Price & You, Angew. Chem., Int. Ed. 2011, 50, Price, Stuart, Zhou, Yang & You, JACS, 2011, 133,

15 Outline I. Past: what we have accomplished? Rational design of conjugated polymers (or molecular engineering) a) Backbone b) Side chains c) Substituents II Current: where we stand now? a) F impact b) Orientation at the D/A interface III Future: what we could do or should do? a) J sc b) V oc c) Stability 15

16 3 Polymers with varied F substitution Minimized other variables 3 different thicknesses to vary transport length Observe trends in J sc, V oc and FF 16

17 Absorption Coefficient (cm -1 ) Normalized Fluoroescence (A.U.) 5x10 4 4x10 4 3x10 4 2x10 4 1x10 4 DTBT DTfBT DTffBT Wavelength (nm) 17

18 DTBT DTfBT DTffBT (a) (b) V oc (V) J sc (ma/cm 2 ) (c) (d) FF (%) Thickness (nm) Thickness (nm) 18

19 1.0 (a) (b) DTBT DTfBT DTffBT Voltage (V) Light Intensity (Suns) FF (%) 19

20 20

21 Repeat unit µ g (Debye) µ e (Debye) µ ge (Debye) BnDT-DTBT µ ge BnDT-DTfBT BnDT-DTffBT

22 In collaboration with John Tumbleston, Harald Ade 22

23 Courtesy of John Tumbleston and Harald Ade 23

24 Edge-on at Interface Face-on Edge-on Face-on at Interface Orientation can be engineered though Materials Chemistry, and choice of solvent for processing Degree of Molecular Orientation Courtesy of John Tumbleston and Harald Ade

25 Outline I. Past: what we have accomplished? Rational design of conjugated polymers (or molecular engineering) a) Backbone b) Side chains c) Substituents II Current: where we stand now? a) F impact b) Orientation at the D/A interface III Future: what we could do or should do? a) J sc b) V oc c) Stability 25

26 J sc (ma/cm 2 ) Band gap (ev) a) Choosing appropriate structural units in D-A polymers b) Increasing Full Width Half Maximum (FWHM) c) Making n-type material absorb d) Improving EQE 26

27 27

28 PCBM Polymer1 Polymer2 a Tandem cell - Tandem: Effectively cover solar spectrum Avoid thermalization losses Complicated fab & costly - + Parallel Circuit ITO + Series Circuit Cathode PBHJ: Much broader absorption Simple device fab Possible energy transfer Polymer1:PCBM b ITO PEDOT:PSS Polymer2:PCBM ITO - ITO + Yang, Zhou, Price & You, JACS, 2012, 134, Parallel-like Bulk Heterojunction ( PBHJ ) 28

29 TAZ HOMO 5.29 ev Band Gap 1.98 ev DTBT HOMO 5.40 ev Band Gap 1.70 ev DTffBT HOMO 5.54 ev Band Gap 1.70 ev DTPyT HOMO 5.45 ev Band Gap 1.51 ev

30 Absorption (a.u.) EQE (%) Current Density (ma/cm 2 ) Absorption (a.u.) EQE (%) Current Density (ma/cm 2 ) TAZ:DTBT TAZ sub-cell DTBT sub-cell Parallel BHJ cell Wavelength (nm) TAZ sub-cell DTBT sub-cell Parallel BHJ cell Wavelength (nm) TAZ sub-cell J sc : 6.53; V oc : 0.73 DTBT sub-cell J sc : 5.68; V oc : 0.81 Parallel BHJ cell J sc : 11.2; V oc : Voltage (V) DTffBT:DTPyT DTffBT sub-cell DTPyT sub-cell Parallel BHJ cell Wavelength (nm) DTffBT sub-cell DTPyT sub-cell Parallel BHJ cell Wavelength (nm) DTffBT sub-cell J sc : 7.86; V oc : 0.89 DTPyT sub-cell J sc : 6.99; V oc : 0.83 Parallel BHJ cell J sc : 13.5; V oc : Voltage (V)

31 EQE (%) J sc (ma/cm 2 ) V oc (V) EQE (%) J sc (ma/cm 2 ) V oc (V) TAZ:DTBT TAZ TAZ:DTBT (0.7:0.3) TAZ:DTBT (0.5:0.5) TAZ:DTBT (0.3:0.7) DTBT Wavelength (nm) J sc V oc % 20% 40% 60% 80% % DTBT wt. (TAZ) % TAZ DTffBT:DTPyT DTffBT DTffBT:DTPyT (0.7:0.3) DTffBT:DTPyT (0.5:0.5) DTffBT:DTPyT (0.3:0.7) DTPyT Wavelength (nm) J sc V oc % 20% 40% 60% 80% 100% DTffBT wt. (DTPyT) % DTPyT

32 V oc (V) HOMO level (ev) a) Further understanding the origin of V oc b) Searching for new acceptors c) Engineering the fullerene 32

33 (a,b) The CT state is significantly lower than any component singlet in the blend. EL emission originates from the CT state only. (c,d) As the CT state energy approaches the energy of the lowest singlet of both blend materials, EL emission is a mixture between CT state emission and component singlet emission. JACS 2012, 134,

34 34

35 Brunetti, Gong, Tong, Heeger, & Wudl Angew. Chem., Int. Ed. 2010, 49,

36 Typically, We do Polycondensation Step Growth X X Y Y [ ] n 36

37 37

38 Ni(dppp)Cl2 is believed to act as an initiator rather than a catalyst McCullough et al. Acc. Chem. Res., 2008, 41 (9),

39 Recommendations I. Further improve the Voc, and esp. the Jsc, via (a) new molecules, (b) new device designs II. Further understanding the loss mechanism, overcome/suppress them via molecular design? III. Stability: can we precisely control the synthesis of polymers? (Also It would impact all PV parameters) IV. We need to work together! Small groups, Centers, etc. 39

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