Les Matériaux Accepteurs pour les Cellules Solaires Organiques

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1 Les Matériaux Accepteurs pour les Cellules olaires rganiques Piétrick HUDHMME JPV 2012 Chantilly - Gouvieux, 13 décembre

2 Planar - and Bulk - Heterojunctions Planar Heterojunction Bulk Heterojunction... e - Al (cathode) A D IT (anode) light glass Al Li Photoactive layer PEDT/P light IT glass... e - e Acceptor Larger p / n interfaces and higher chance of exciton formation and separation 2 Donor

3 Planar - and Bulk - Heterojunctions IT ev Voc Al ev A. Mishra, P. Bäuerle, Angew. Chem. Int. Ed., 2012, 51,

4 rganic non-ullerene and ullerene based acceptors on ullerene Acceptors P. onar, J. P.. Lim, K. L. Chan, Energy Environ. ci., 2011, 4, 1558 ullerene-based Acceptors P. Hudhomme, J. Cousseau, ullerenes, principles and applications 2nde ed., C Publishing. Langa and J.-. ierengarten eds 2011, Chapter 12, 416 C. Li, H. Yip, A. Jen, J. Mater. Chem., 2012, 22,

5 rganic non-ullerene acceptors on ullerene Acceptors P. onar, J. P.. Lim, K. L. Chan, Energy Environ. ci., 2011, 4, 1558 ullerene-based Acceptors P. Hudhomme, J. Cousseau, ullerenes, principles and applications 2nde ed., C Publishing. Langa and J.-. ierengarten eds 2011, Chapter 12, 416 C. Li, H. Yip, A. Jen, J. Mater. Chem., 2012, 22,

6 C. W. Tang, Appl. Phys. Lett., 1986, 48, 183 CuPc PTCBI = Tang s solar cell Bilayer Planar - Heterojunction : C.W. Tang (1986) 1% Cu Cu-Pc PTCBI anti ACCEPT = PTCBI 3,4,9,10-Perylene TetraCarboxylic bisbenzimidazole (mixture of syn and anti isomers) PTCBI syn yn = 0.93% Anti = 1.1 %.B. im et al.,, Appl. Phys. Lett., 2007, 91, PTCBI anti CuPc = 30 nm PTCBI = 50 nm = 0.65 PCE 6 = 0.95%

7 ylene diimide - based acceptors oluble processable perylenediimide (PDI) acceptors : ' ' ' ' ' ' planar b a c 3.49 Å twisted. Würthner, Chem. Commun., 2004,

8 ylene diimide - based acceptors Coronenes for Discotic Liquid Crystals : Blend HCB / PDI K. Müllen and coll, ol. Energy Mater. ol. Cells, 2010, 94, 560 Peri-hexabenzocoronene(HCB) Perylene azodicarboxyldiimide 8 Coronene monoimide

9 ylene diimide - based acceptors C C 2 e 2 C C C C Bulk Heterojunction : IT / PEDT:P / Donor : Acceptor / Al Voc = 0.9 V; Jsc = 8.30 ma/cm2; = 0.52; PCE = 3.88% The highest efficiency reported for a bulk-heteojunction solar cell that does not contain fullerene. J.A. Mikroyannidis and coll., ol. Energy Mater. ol. Cells, 2009, 93,

10 Diketopyrrolopyrrole - based acceptors - Excellent performance as donor materials in bulk heterojunction solar cells Y. Zhu and coll., Beilstein J. rg. Chem., 2010, 6, Enhanced electron affinity by introducing electron withdrawing groups C 12 H 25 EW G C 3 C 12 H 25 EWG C 3 C 3 Bulk Heterojunction : IT / P3HT : DPP / Al Voc = 0.81 V; Jsc = 2.36 ma/cm2; = 0.52; PCE = 1.0 % Z.K. Chen and coll., J. Mater. Chem., 2010, 20,

11 verview of small molecular acceptors Cyano PPV : ubphthalocyanines : C C 8 H 17 C 8 H 17 C Voc = 1.36 V; PCE = 1.7 % D. eher and coll., Chem. Mater., 2005, 17, 6532 n PCE = 0.96 % B Cl T. Torres and coll., Adv. unct. Mater., 2009, 19, 3435 Vinazene based oligomers : C C PCE = 1.4 % C C J. M. J. rechet and coll., Chem. Mater., 2010, 22, ,9 -Bifluorenylidenes : Me Me Voc = 1.10 PCE = 1.7% IT / PEDT:P / P3HT 11 : Acceptor / Ba/ Al. Wudl and coll., Ang. Chem. Int. Ed., 2010, 49, 532

12 rganic non-ullerene acceptors on ullerene Acceptors P. onar, J. P.. Lim, K. L. Chan, Energy Environ. ci., 2011, 4, 1558 or a new generation of PV acceptors : - arrow bandgap and high extinction coefficient - High LUM energy level to increase Voc - High electron mobility - Morphological compatibility with polymers Towards ullerene-based Acceptors : rom one- to three- dimensional acceptors 12

13 rganic ullerene based acceptors on ullerene Acceptors P. onar, J. P.. Lim, K. L. Chan, Energy Environ. ci., 2011, 4, 1558 ullerene-based Acceptors P. Hudhomme, J. Cousseau, ullerenes, principles and applications 2nde ed., C Publishing. Langa and J.-. ierengarten eds 2011, Chapter 12, 416 C. Li, H. Yip, A. Jen, J. Mater. Chem., 2012, 22,

14 ullerenes C60 and C : Discovery of C : ynthesis of C60 and X-ray crystal structure 1992 : Evidence of photoinduced electron tranfer with polymer donors 1996 : obel Prize for H. Kroto,,. malley,,. Curl C60 : C60 : 80-85% C70 : 10-15% $ / g in $ / g in 2012 C70 : $ / g in trong electron mobility : 6 cm2 V-1 s-1 - High electron affinity 14

15 C60 et C70 PCBM Increasing of solubility CH 3. Wudl and coll., J. rg. Chem., 1995, 60, 532 C60 [60]PCBM Increasing of absorption CH 3 H 3 C CH 3 [70]PCBM α isomer (85%) β isomer (15%). A. J. Janssen and coll., Angew. Chem. Int. Ed., , 42, 3371

16 C60 and C70 PCBM ptimization of the p-type polymer structure but much less work on p-type fullerenes CH 3 H 17C 8 C 8 H 17 C 12 H 25 2 m PVT C 6 H 13 n Br C 12 H 25 PTPTB n Br AP-Green 5 = -CH 2 CH(C 2 H 5 )C 4 H 9 n [70]PCBM H 17 C 8 C 8H 17 AP 3 n H 21 C 10 C 10H 21 P10TBT n PCPDTBT n yield 6 (%) year H 17 C 8 C 8 H 17 H 17C 8 i C 8H 17 1 C 2 2 n CH 3 PCDTBT n Pi-DBT n PTB1 = H 1 = C 12 H 25 2 = C 8 H 17 PTB4 = 1 =C 8 H 17 2 = -CH 2 CH(C 2 H 5 )C 4 H 9 16 [60]PCBM

17 C60 and C70 PCBM CH 3 CH 3 E LUM(D) [60]PCBM [70]PCBM Eg E LUM = 0.3 ev LUM[60]PCBM LUM[70]PCBM VC HM(D ) E HM HM[60]PCBM HM[70]PCBM D ACCEPT Limitation : A relative low LUM level of PCBM limits the Voc. Wudl and coll. J. Mater. Chem. 2010, 20,

18 Modifications of C60 PCBM Modification of the Aromatic Group Modification fo the chain length (CH 2 ) n CH 3 CH 3 n = 2 à 6 [60]PCBM Modification of the terminal function C n H 2n+1 CH2 (C 2 ) 6 C 3 H C 4 H 9 18

19 Modifications du C60 PCBM Modification of the attachment Me CH 2 Ph C 3 2 C 3 CH 2 Ph C 3 C 3 2 CH 3 PY [60]BTP [70]BTP [60]PCBM CH 3 [60]CMA Comparable results with P3HT:[60]PCBM J. M. J. rechet and coll., Chem. Mater., 2007, 19, 2927 [60]APCBM 19

20 Modifications of C60 PCBM ynthesis of Bis-adducts CH 3 i. C60 ii. Monoadduit iii. Bisadduit iv. Multiadduit CH 3 [60]PCBM bisadduct - LUM : 0.1 ev higher - Enhanced Voc 0.73 V which is 0.15 V higher than P3HT : PCBM - Higher PCE : 4.5% compared to 3.8 % with P3HT J. C. Hummelen and coll., Adv. Mater., 2008, 20,

21 Indene C60 Bis-adduct : IC60BA Diels-Alder reaction ICMA + ICBA - ICBA = Mixture of 16 isomers + ICTA Y. Li and coll., J. Am. Chem. oc., 2010, 132, 1377 B. J. Kim and coll., Appl. Mater. Interfaces, 2012, 4, 110 PCBM ICMA ICBA ICTA 21

22 Indene C60 Bis-adduct : IC60BA Y. Li and coll., Adv. Mater., 2010, 22, 4355 ICBA E1 (V, vs Ag/Ag+) ICMA ICBA PCBM ICMA PCBM 22

23 Indene C70 Bis-adduct : IC70BA Y. Li and coll., Adv. unct. Mater., 2010, 20, 3383 [70]ICBA - LUM : 0.19 ev higher than this of PCBM 23

24 Conclusion and current Trends - Increasing the fullerene derivatives absorption : Concept of «super-absorbing fullerenes»: C 5 H 11 C 60 -PDI dyad P. Hudhomme,. M. Williams and coll., J. Phys. Chem. A, 2006, 110, C 2 C-PC 70 BM - LUM : 0.15 ev higher than this of PC70BM - P3HT : PC70BM : Voc = 0.66 V; Jsc = 9.40 ma/cm2; = 0.52; PCE = 3.23 % - P3HT : C-PC70BM : Voc = 0.82 V; Jsc = ma/cm2; = 0.56; PCE = 4.88 %. P. ingh and coll., Adv. unct. Mater., 2012, 22,

25 Conclusion and current Trends Blend P3HT / PCBM Blend P3HT / Cross linkable fullerene G. Wantz, L. Derue,. Dautel, B. Pavageau, A. Diacon, P. Hudhomme, A Cephorcas, Programme Habisol : Patent deposited in April

26 EMECIEMET : A Cephorcas (HABIL ) : - IM Bordeaux (G. Wantz, L. Derue, L. Hirsch) - EC Montpellier AM2 (. Dautel) - IPEM Pau (C. Dagron-Lartigau,. Hiorns) - Institut Chimie Clermont-errand (A. ivaton, J.-L. Gardette) - hodia Bordeaux (B. Pavageau) University of Amsterdam :. M. Williams MLTECH-Anjou (Université d Angers) : - A. Diacon - J. Baffreau -. Leroy-Lhez Thank you very much for your attention 26