Calculation of solid state molecular ionisation energies and electron affinities for organic semiconductors

Organic Electronics

Volumn 12, Issue 2, 2011, Pages 394-403

  Schwenn, P E ^a   Burn, P L ^a   Powell, B J ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Cancellation of errors; Density functional theory; Electron affinity; Ionisation energy; Polarizable continuum model

Indexed keywords

CONTINUUM MECHANICS; DENSITY FUNCTIONAL THEORY; EIGENVALUES AND EIGENFUNCTIONS; ELECTRONS; ERRORS; MOLECULAR ORBITALS; OPTOELECTRONIC DEVICES;

IONISATION ENERGIES; MOLECULAR ORBITAL ENERGY; MOLECULAR SEMICONDUCTORS; ORGANIC ELECTRONICS; ORGANIC OPTOELECTRONICS; ORGANIC PHOTOVOLTAICS; POLARIZABLE CONTINUUM MODEL; SOLID-STATE ELECTRON;

ELECTRON AFFINITY;

EID: 78651247764     PISSN: 15661199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orgel.2010.11.025     Document Type: Article

References (96)

1. A.J. Heeger, N.S. Sariciftci, and E.B. Namdas Semiconducting and Metallic Polymers 2010 Oxford University Press
2. N. Ashcroft, and N. Mermin Solid State Physics 1976 Holt, Rinehart and Winston
3. J. Bardeen, and W.H. Brattain The transistor, a semi-conductor triode Phys. Rev. 74 1948 230 231
4. J. Bardeen, and W.H. Brattain Physical principles involved in transistor action Phys. Rev. 75 1949 1208 1225
5. L. Hoddeson, V. Daitch, True genius: the life and science of John Bardeen: the only winner of two Nobel Prizes in Physics, Joseph Henry Pr, 2002.
6. S. Braun, W. Salaneck, and M. Fahlman Energy-level alignment at organic/metal and organic/organic interfaces Adv. Mater. 21 2009 1450 1472
7. P. Fulde Electron Correlations in Molecules and Solids 1995 Springer
8. E. Scriven, and B.J. Powell Toward the parametrization of the hubbard model for salts of bis(ethylenedithio)tetrathiafulvalene: a density functional study of isolated molecules J. Chem. Phys. 130 2009 104508
9. E. Scriven, and B.J. Powell Effective coulomb interactions within BEDT-TTF dimers Phys. Rev. B 80 2009 205107
10. I.B. Bersuker The Jahn-Teller Effect 2006 Cambridge University Press
11. I.G. Hill, A. Kahn, Z.G. Soos, and R.A. Pascal Jr. Charge-separation energy in films of [pi]-conjugated organic molecules Chem. Phys. Lett. 327 2000 181 188
12. B.W. D'Andrade, S. Datta, S.R. Forrest, P. Djurovich, E. Polikarpov, and M.E. Thompson Relationship between the ionization and oxidation potentials of molecular organic semiconductors Org. Electron. 6 2005 11 20
13. P.I. Djurovich, E.I. Mayo, S.R. Forrest, and M.E. Thompson Measurement of the lowest unoccupied molecular orbital energies of molecular organic semiconductors Org. Electron. 10 2009 515 520
14. P.K. Nayak, and N. Periasamy Calculation of electron affinity, ionization potential, transport gap, optical band gap and exciton binding energy of organic solids using 'solvation' model and DFT Org. Electron. 10 2009 1396 1400
15. P. Nayak, and N. Periasamy Calculation of ionization potential of amorphous organic thin-films using solvation model and DFT Org. Electron. 10 2009 532 535
16. J.C. Rienstra-Kiracofe, G.S. Tschumper, H.F. Schaefer, S. Nandi, and G.B. Ellison Atomic and molecular electron affinities: photoelectron experiments and theoretical computations Chem. Rev. 102 2002 231 282
17. R.O. Jones, and O. Gunnarsson The density functional formalism, its applications and prospects Rev. Mod. Phys. 61 1989 689 746
18. W. Koch, M. Holthausen, and M. Holthausen A Chemist's Guide to Density Functional Theory 2000 Wiley Online Library
19. L.J. Sham, and W. Kohn One-particle properties of an inhomogeneous interacting electron gas Phys. Rev. 145 1966 561 567
20. P. Politzer, and F. Abu-Awwad A comparative analysis of Hartree-Fock and Kohn-Sham orbital energies Theor. Chem. Acc. 99 1998 83 87
21. J.F. Janak Proof that ∂e∂ ni = in density-functional theory Phys. Rev. B 18 1978 7165 7168
22. C.-O. Almbladh, and U. von Barth Exact results for the charge and spin densities, exchange-correlation potentials, and density-functional eigenvalues Phys. Rev. B 31 1985 3231
23. J.P. Perdew, R.G. Parr, M. Levy, and J.L. Balduz Density-functional theory for fractional particle number: derivative discontinuities of the energy Phys. Rev. Lett. 49 1982 1691
24. A. Cohen, P. Mori-Sanchez, and W. Yang Insights into current limitations of density functional theory Science 321 2008 792
25. M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S. Su, T.L. Windus, M. Dupuis, and J.A.M. Jr General atomic and molecular electronic structure system J. Comput. Chem. 14 1993 1347 1363
26. A.D. Becke Density-functional thermochemistry. iii. the role of exact exchange J. Chem. Phys. 98 1994 5648 5652
27. P.J. Stephens, F. Devlin, C. Chabalowski, and M. Frisch Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields J. Chem. Phys. 98 1994 11623 11627
28. E. Lewars Computational Chemistry: Introduction to the Theory and Applications of Molecular and Quantum Mechanics 2003 Springer
29. P. Warner Ab initio calculations on heteroatomic systems using density functional theory and diffuse basis functions J. Org. Chem. 61 1996 7192 7194
30. N. Sato, Y. Saito, and H. Shinohara Threshold ionization energy of C 60 in the solid state Chem. Phys. 162 1992 433 438
31. R. Schwedhelm, L. Kipp, A. Dallmeyer, and M. Skibowski Experimental band gap and core-hole electron interaction in epitaxial C 60 films Phys. Rev. B 58 1998 13176 13180
32. V. de Coulon, J.L. Martins, and F. Reuse Electronic structure of neutral and charged c 60 clusters Phys. Rev. B 45 1992 13671 13675
33. M.R. Pederson, and A.A. Quong Polarizabilities, charge states, and vibrational modes of isolated fullerene molecules Phys. Rev. B 46 1992 13584 13591
34. R.L. Martin, and J.P. Ritchie Coulomb and exchange interactions in c 60 n - Phys. Rev. B 48 1993 4845 4849
35. J. Tomasi, and M. Persico Molecular interactions in solution: an overview of methods based on continuous distributions of the solvent Chem. Rev. 94 1994 2027 2094
36. M. Connolly The molecular surface package J. Mol. Graph. 11 1993 139 141
37. H. Kurtz, J. Stewart, and K. Dieter Calculation of the nonlinear optical properties of molecules J. Comput. Chem. 11 1990 82 87
38. N. Sato, K. Seki, and H. Inokuchi Polarization energies of organic solids determined by ultraviolet photoelectron spectroscopy J. Chem. Soc. Faraday Trans. 2 77 1981 1621 1633
39. P. Nielsen, A. Epstein, and D. Sandman Photoemission studies of TCNQ compounds Solid State Commun. 15 1974 53 58
40. R. Murdey, and W. Salaneck Charge injection barrier heights across multilayer organic thin films Jpn. J. Appl. Phys. 44 2005 3751
41. W. Gao, and A. Kahn Electronic structure and current injection in zinc phthalocyanine doped with tetrafluorotetracyanoquinodimethane: Interface versus bulk effects Org. Electron. 3 2002 53 63
42. K. Akaike, K. Kanai, H. Yoshida, J. Tsutsumi, T. Nishi, N. Sato, Y. Ouchi, and K. Seki Ultraviolet photoelectron spectroscopy and inverse photoemission spectroscopy of [6,6]-phenyl- c 61 -butyric acid methyl ester in gas and solid phases J. Appl. Phys. 104 2008 023710
43. Z. Guan, J. Kim, H. Wang, C. Jaye, D. Fischer, Y. Loo, and A. Kahn Direct determination of the electronic structure of the poly (3-hexylthiophene): phenyl-[6, 6]-C61 butyric acid methyl ester blend Org. Electron. 11 2010 1779
44. J. Seo, S. Kang, C. Kim, S. Cho, K. Yoo, and C. Whang Energy level alignment between C 60 and Al using ultraviolet photoelectron spectroscopy Appl. Surf. Sci. 252 2006 8015 8017
45. F. Zhang, A. Vollmer, J. Zhang, Z. Xu, J. Rabe, and N. Koch Energy level alignment and morphology of interfaces between molecular and polymeric organic semiconductors Org. Electron. 8 2007 606 614
46. W. Zhao, and A. Kahn Charge transfer at n-doped organic-organic heterojunctions J. Appl. Phys. 105 2009 123711
47. Y. Ge, and J. Whitten Energy level alignment between sexithiophene and buckminsterfullerene films Chem. Phys. Lett. 448 2007 65 69
48. M. Ruckman, B. Xia, and S. Qiu Adsorption of C 60 on Ta(110): Photoemission and C K-edge studies Phys. Rev. B 48 1993 15457
49. J. Weaver, J. Martins, T. Komeda, Y. Chen, T. Ohno, G. Kroll, N. Troullier, R. Haufler, and R. Smalley Electronic structure of solid C 60 : experiment and theory Phys. Rev. Lett. 66 1991 1741
50. A. Maxwell, P. Brühwiler, D. Arvanitis, J. Hasselström, and N. Mrtensson C 1s ionisation potential and energy referencing for solid C 60 films on metal surfaces Chem. Phys. Lett. 260 1996 71 77
51. L. Lyons, and G. Morris 1000. Photo-and semi-conductance in organic crystals. Part VIII. Photo-emission of electrons from crystals of aromatic hydrocarbons J. Chem. Soc. 1960 1960 5192 5199
52. R. Katoh, and M. Kotani External photoemission by singlet-exciton photoionization in an anthracene single crystal Chem. Phys. Lett. 174 1990 537 540
53. S. Hino, T. Hirooka, and H. Inokuchi Photoemission from anthracene and compounds containing anthracene-ring systems Bull. Chem. Soc. Jpn. 50 1977 620 625
54. F.I. Vilesov, and D.A. Sukhov Soviet Physics-Solid State 13 1971 2300
55. A.P. Marchetti, and D.R. Kearns Photoelectron emission from aromatic and metallooraganic hydrocarbons Soviet Physics-Solid State 6 1970 299
56. N. Karl, N. Sato, K. Seki, and H. Inokuchi UV photoelectron spectroscopy of several one-and two-component organic photoconductors J. Chem. Phys. 77 1982 4870
57. A. Zakhidov, and K. Yoshino Polarization double barriers at the interfaces in organic multilayered structures and superlattices Synth. Met. 64 1994 155 165
58. N. Sato, K. Seki, H. Inokuchi, and Y. Harada Photoemission from an amorphous pentacene film Chem. Phys. 109 1986 157 162
59. H. Fukagawa, H. Yamane, T. Kataoka, S. Kera, M. Nakamura, K. Kudo, and N. Ueno Origin of the highest occupied band position in pentacene films from ultraviolet photoelectron spectroscopy: hole stabilization versus band dispersion Phys. Rev. B 73 2006 245310
60. F. Amy, C. Chan, and A. Kahn Polarization at the gold/pentacene interface Org. Electron. 6 2005 85 91
61. Y. Hirose, W. Chen, E.I. Haskal, S.R. Forrest, and A. Kahn Band lineup at an organic-inorganic semiconductor heterointerface: perylenetetracarboxylic dianhydride/GaAs(100) Appl. Phys. Lett. 64 1994 3482 3484
62. N. Karl, and N. Sato UV-photoelectron spectroscopy of one-and two component organic crystals Mol. Cryst. Liq. Cryst. 218 1992 79 84
63. D.R. Zahn, G.N. Gavrila, and M. Gorgoi The transport gap of organic semiconductors studied using the combination of direct and inverse photoemission Chem. Phys. 325 2006 99 112
64. N. Sato, H. Yoshida, and K. Tsutsumi Unoccupied electronic structure in organic thin films studied by inverse photoemission spectroscopy J. Mater. Chem. 10 2000 85 89
65. J. Sauther, J. Wüsten, S. Lach, and C. Ziegler Gas phase and bulk ultraviolet photoemission spectroscopy of 3,4,9,10-perylene-tetracarboxylic dianhydride, 1,4,5,8-naphthalene-tetracarboxylic dianhydride, and 1,8-naphthalene-dicarboxylic anhydride J. Chem. Phys. 131 2009 034711
66. H.-Y. Chen, J. Hou, S. Zhang, Y. Liang, G. Yang, Y. Yang, L. Yu, Y. Wu, and G. Li Polymer solar cells with enhanced open-circuit voltage and efficiency Nat. Photon 3 2009 649 653
67. R. Schlaf, P.G. Schroeder, M.W. Nelson, B.A. Parkinson, P.A. Lee, K.W. Nebesny, and N.R. Armstrong Observation of strong band bending in perylene tetracarboxylic dianhydride thin films grown on SnS 2 J. Appl. Phys. 86 1999 1499 1509
68. S. Duhm, A. Gerlach, I. Salzmann, B. Bröker, R. Johnson, F. Schreiber, and N. Koch PTCDA on Au (1 1 1), Ag (1 1 1) and Cu (1 1 1): correlation of interface charge transfer to bonding distance Org. Electron. 9 2008 111 118
69. H. Yamane, S. Kera, K. Okudaira, D. Yoshimura, K. Seki, and N. Ueno Intermolecular energy-band dispersion in PTCDA multilayers Phys. Rev. B 68 2003 33102
70. W. Osikowicz, M. de Jong, and W. Salaneck Formation of the interfacial dipole at organic-organic interfaces: C 60 /polymer interfaces Adv. Mater. 19 2007 4213 4217
71. K. Kanai, T. Miyazaki, H. Suzuki, M. Inaba, Y. Ouchi, and K. Seki Effect of annealing on the electronic structure of poly (3-hexylthiophene) thin film Phys. Chem. Chem. Phys. 12 2010 273 282
72. Y. Sohn, and J. Stuckless Characteristics of photoexcitations and interfacial energy levels of regioregular poly (3-hexythiophene-2, 5-diyl) on gold ChemPhysChem 8 2007 1937 1942
73. J.E. Lyon, A.J. Cascio, M.M. Beerbom, R. Schlaf, Y. Zhu, and S.A. Jenekhe Photoemission study of the poly(3-hexylthiophene)/Au interface Appl. Phys. Lett. 88 2006 222109
74. A.J. Cascio, J.E. Lyon, M.M. Beerbom, R. Schlaf, Y. Zhu, and S.A. Jenekhe Investigation of a polythiophene interface using photoemission spectroscopy in combination with electrospray thin-film deposition Appl. Phys. Lett. 88 2006 062104
75. D. Schmeißer Valence states of poly (3-hexyl-thiophene) as probed by photoelectron spectra at resonant excitation Synth. Met. 138 2003 135 140
76. M. Onoda, K. Tada, A. Zakhidov, and K. Yoshino Photoinduced charge separation in photovoltaic cell with heterojunction of p-and n-type conjugated polymers Thin Solid Films 331 1998 76 81
77. K. Kanai, K. Akaike, K. Koyasu, K. Sakai, T. Nishi, Y. Kamizuru, T. Nishi, Y. Ouchi, and K. Seki Determination of electron affinity of electron accepting molecules Appl. Phys. A: Mater. Sci. Process. 95 2009 309 313
78. P. Yannoulis, K.-H. Frank, and E.-E. Koch Electronic structure and orientation of anthracene on Ag(1 1 1) Surf. Sci. 241 1991 325
79. K.H. Frank, P. Yannoulis, R. Dudde, and E.E. Koch Unoccupied molecular orbitals of aromatic hydrocarbons adsorbed on Ag(1 1 1) J. Chem. Phys. 89 1988 7569 7576
80. V. Mihailetchi, J. van Duren, P. Blom, J. Hummelen, R. Janssen, J. Kroon, M. Rispens, W. Verhees, and M. Wienk Electron transport in a methanofullerene Adv. Funct. Mater. 13 2003 43 46
81. P.C. Eklund, A.M. Rao, Y. Wang, P. Zhou, K.-A. Wang, J.M. Holden, M.S. Dresselhaus, and G. Dresselhaus Optical properties of C 60 - and C 7 0 -based solid films Thin Solid Films 257 1995 211 232
82. P. Cummins, and D. Dunmur The electric permittivity of crystalline anthracene J. Phys. D: Appl. Phys. 7 1974 451
83. T. Li, J.W. Balk, P.P. Ruden, I.H. Campbell, and D.L. Smith Channel formation in organic field-effect transistors J. Appl. Phys. 91 2002 4312 4318
84. D.Y. Zang, F.F. So, and S.R. Forrest Giant anisotropies in the dielectric properties of quasi-epitaxial crystalline organic semiconductor thin films Appl. Phys. Lett. 59 1991 823 825
85. F.F. So, and S.R. Forrest Evidence for exciton confinement in crystalline organic multiple quantum wells Phys. Rev. Lett. 66 1991 2649 2652
86. K.B. Krueger, personal communication, unpublished data (2010).
87. S.P. Park, S.S. Kim, J.H. Kim, C.N. Whang, and S. Im Optical and luminescence characteristics of thermally evaporated pentacene films on Si Appl. Phys. Lett. 80 2002 2872 2874
88. J.-L. Brédas, J.E. Norton, J. Cornil, and V. Coropceanu Molecular understanding of organic solar cells: the challenges Acc. Chem. Res. 42 2009 1691 1699
89. J. Cornil, V. Lemaur, M.C. Steel, H. Dupin, A. Burquel, D. Beljonne, J.-L. Bredás, in: S.S. Sun, N.S. Sariciftci (Eds.), Organic Photovoltaics: Mechanism, Materials, and Devices, CRC.
90. R.A. Marcus Electron transfer reactions in chemistry. theory and experiment Rev. Mod. Phys. 65 1993 599 610
91. N. Sato, H. Inokuchi, and E.A. Silinsh Reevaluation of electronic polarization energies in organic molecular crystals Chem. Phys. 115 1987 269 277
92. S. Krause, M. Casu, A. Schöll, and E. Umbach Determination of transport levels of organic semiconductors by UPS and IPS New J. Phys. 10 2008 085001
93. N. Smith Inverse photoemission Rep. Prog. Phys. 51 1988 1227 1294
94. E. Tsiper, Z. Soos, W. Gao, and A. Kahn Electronic polarization at surfaces and thin films of organic molecular crystals: PTCDA Chem. Phys. Lett. 360 2002 47 52
95. S. Tadayyon, H. Grandin, K. Griffiths, L. Coatsworth, P. Norton, H. Aziz, and Z. Popovic Reliable and reproducible determination of work function and ionization potentials of layers and surfaces relevant to organic light emitting diodes Org. Electron. 5 2004 199 205
96. I. Hill, A. Kahn, J. Cornil, D. dos Santos, and J. Bredas Occupied and unoccupied electronic levels in organic π-conjugated molecules: comparison between experiment and theory Chem. Phys. Lett. 317 2000 444 450