Pentacene on Au(1 1 1), Ag(1 1 1) and Cu(1 1 1): From physisorption to chemisorption

Journal of Physics Condensed Matter

Volumn 28, Issue 9, 2016, Pages

  Lu, Meng Chao ^a   Wang, Rong Bin ^a   Yang, Ao ^a   Duhm, Steffen ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

energy level alignment; organic thin film; pentacene; photoelectron spectroscopy

Indexed keywords

CHARGE TRANSFER; CHEMISORPTION; ELECTRONIC STRUCTURE; ELECTRONS; FILM GROWTH; FILM PREPARATION; MOLECULAR ORBITALS; MONOLAYERS; MULTILAYER FILMS; MULTILAYERS; PHOTOELECTRON SPECTROSCOPY; PHOTOELECTRONS; PHOTONS; SILVER; SURFACE STRUCTURE; THIN FILMS; ULTRAVIOLET PHOTOELECTRON SPECTROSCOPY;

DEGREE OF CRYSTALLINITY; ELECTRONIC CHARACTERISTICS; ENERGY LEVEL ALIGNMENT; LOWEST UNOCCUPIED MOLECULAR ORBITAL; MOLECULAR MONOLAYER; MOLECULAR SURFACES; ORGANIC THIN FILMS; PENTACENES;

SUBSTRATES;

EID: 84959574146     PISSN: 09538984     EISSN: 1361648X     Source Type: Journal    
DOI: 10.1088/0953-8984/28/9/094005     Document Type: Article

References (79)

1. Kahn A, Koch N and Gao W 2003 Electronic structure and electrical properties of interfaces between metals and π-conjugated molecular films J. Polym. Sci. B 41 2529-48
2. Salaneck W R, Seki K, Kahn A and Pireaux J (ed) 2001 Conjugated Polymer and Molecular Interfaces: Science and Technology for Photonic and Optoelectronic Application (New York: Dekker)
3. Koch N, Ueno N and Wee A T S (ed) 2013 The Molecule-Metal Interface (New York: Wiley)
4. Ou Q D, Li C, Li Y Q and Tang J X 2015 Photoemission spectroscopy study on interfacial energy level alignments in tandem organic light-emitting diodes J. Electron Spectrosc. Relat. Phenom. 204 186-95
5. Li H, Duan Y, Coropceanu V and Bredas J L 2009 Electronic structure of the pentacene-gold interface: a density-functional theory study Org. Electron. 10 1571-8
6. Horowitz G 2004 Organic thin film transistors: from theory to real devices J. Mater. Res. 19 1946-62
7. Ishii H, Sugiyama K, Ito E and Seki K 1999 Energy level alignment and interfacial electronic structures at organic/metal and organic/organic interfaces Adv. Mater. 11 605-25
8. Greiner M T, Helander M G, Tang W M, Wang Z B, Qiu J and Lu Z H 2012 Universal energy-level alignment of molecules on metal oxides Nat. Mater. 11 76-81
9. Braun S, Salaneck W R and Fahlman M 2009 Energy-level alignment at organic/metal and organic/organic interfaces Adv. Mater. 21 1450-72
10. Hill I G, Rajagopal A, Kahn A and Hu Y 1998 Molecular level alignment at organic semiconductor-metal interfaces Appl. Phys. Lett. 73 662-4
11. Kowarik S, Gerlach A and Schreiber F 2008 Organic molecular beam deposition: fundamentals, growth dynamics, and in situ studies J. Phys.: Condens. Matter 20 184005
12. Chen X L, Lovinger A J, Bao Z and Sapjeta J 2001 Morphological and transistor studies of organic molecular semiconductors with anisotropic electrical characteristics Chem. Mater. 13 1341-8
13. Lee S, Koo B, Shin J, Lee E, Park H and Kim H 2006 Effects of hydroxyl groups in polymeric dielectrics on organic transistor performance Appl. Phys. Lett. 88 162109
14. Lee J, Jadhav P, Reusswig P D, Yost S R, Thompson N J, Congreve D N, Hontz E, Van Voorhis T and Baldo M A 2013 Singlet exciton fission photovoltaics Acc. Chem. Res. 46 1300-11
15. Chang J, Chi C, Zhang J and Wu J 2013 Controlled growth of large-area high-performance small-molecule organic single-crystalline transistors by slot-die coating using a mixed solvent system Adv. Mater. 25 6442-7
16. Sheraw C D, Jackson T N, Eaton D L and Anthony J E 2003 Functionalized pentacene active layer organic thin-film transistors Adv. Mater. 15 2009-11
17. Sheraw C D, Zhou L, Huang J R, Gundlach D J, Jackson T N, Kane M G, Hill I G, Hammond M S, Campi J and Greening B K 2002 Organic thin-film transistor-driven polymer-dispersed liquid crystal displays on flexible polymeric substrates Appl. Phys. Lett. 80 1088-90
18. Soe W H, Manzano C, De Sarkar A, Chandrasekhar N and Joachim C 2009 Direct observation of molecular orbitals of pentacene physisorbed on Au (1 1 1) by scanning tunneling microscope Phys. Rev. Lett. 102 176102
19. Toyoda K, Hamada I, Lee K, Yanagisawa S and Morikawa Y 2010 Density functional theoretical study of pentacene/noble metal interfaces with van der Waals corrections: vacuum level shifts and electronic structures J. Chem. Phys. 132 134703
20. Schroeder P G, France C B, Park J B and Parkinson B A 2002 Energy level alignment and 2D structure of pentacene on Au(1 1 1) surfaces J. Appl. Phys. 91 3010
21. Käfer D, Ruppel L and Witte G 2007 Growth of pentacene on clean and modified gold surfaces Phys. Rev. B 75 085309
22. Dougherty D B, Jin W, Cullen W G, Reutt-Robey J E and Robey S W 2008 Variable temperature scanning tunneling microscopy of pentacene monolayer and bilayer phases on Ag(1 1 1) J. Phys. Chem. C 112 20334-9
23. Mete E, Demiroʇlu ̄, Danişman M F and Ellialtioʇlu Ş 2010 Pentacene multilayers on Ag (1 1 1) surface J. Phys. Chem. C 114 2724-9
24. Käfer D and Witte G 2007 Evolution of pentacene films on Ag(1 1 1): growth beyond the first monolayer Chem. Phys. Lett. 442 376-83
25. Eremtchenko M, Temirov R, Bauer D, Schaefer J A and Tautz F S 2005 Formation of molecular order on a disordered interface layer: Pentacene/Ag(1 1 1) Phys. Rev. B 72 115430
26. Duhm S, Bürker C, Niederhausen J, Salzmann I, Duvernay J, Kera S, Schreiber F, Koch N, Ueno N and Gerlach A 2013 Pentacene on Ag(1 1 1): correlation of bonding distance with intermolecular interaction and order ACS Appl. Mater. Interfaces 5 9377-81
27. Toyoda K, Nakano Y, Hamada I, Lee K, Yanagisawa S and Morikawa Y 2009 First-principles study of the pentacene/Cu (1 1 1) interface: adsorption states and vacuum level shifts J. Electron Spectrosc. Relat. Phenom. 174 78-84
28. Koch N et al 2008 Adsorption-induced intramolecular dipole: correlating molecular conformation and interface electronic structure J. Am. Chem. Soc. 130 7300-4
29. Yamane H, Kanai K, Ouchi Y, Ueno N and Seki K 2009 Impact of interface geometric structure on organic-metal interface energetics and subsequent films electronic structure J. Electron Spectrosc. Relat. Phenom. 174 28-34
30. Smerdon J A, Bode M, Guisinger N P and Guest J R 2011 Monolayer and bilayer pentacene on Cu(1 1 1) Phys. Rev. B 84 165436
31. France C B, Schroeder P G, Forsythe J C and Parkinson B A 2003 Scanning tunneling microscopy study of the coverage-dependent structures of pentacene on Au (1 1 1) Langmuir 19 1274-81
32. Kang J H and Zhu X Y 2003 Pi-stacked pentacene thin films grown on Au (1 1 1) Appl. Phys. Lett. 82 3248-50
33. Duhm S et al 2010 Influence of intramolecular polar bonds on interface energetics in perfluoro-pentacene on Ag (1 1 1) Phys. Rev. B 81 045418
34. Koch N, Vollmer A, Duhm S, Sakamoto Y and Suzuki T 2007 The effect of fluorination on pentacene/gold interface energetics and charge reorganization energy Adv. Mater. 19 112-6
35. Kang J H, Zhu X Y, Park J B and Parksin B A 2006 Layer-by-layer growth of incommensurate, polycrystalline, lying-down pentacene thin films on Au(1 11) Chem. Mater. 18 1318-23
36. Schroeder P G and France C B 2003 Orbital alignment and morphology of pentacene deposited on Au(1 1 1) and SnS2 studied using photoemission spectroscopy J. Phys. Chem. B 107 2253-61
37. Jaeckel B, Sambur J B and Parkinson B A 2008 The influence of metal work function on the barrier heights of metal/pentacene junctions J. Appl. Phys. 103 063719
38. Koch N, Salzmann I, Johnson R L, Pflaum J, Friedlein R and Rabe J P 2006 Molecular orientation dependent energy levels at interfaces with pentacene and pentacenequinone Org. Electron. 7 537-45
39. Zheng Y, Qi D, Chandrasekhar N, Gao X, Troadec C and Wee A T S 2007 Effect of molecule-substrate interaction on thin-film structures and molecular orientation of pentacene on silver and gold Langmuir 23 8336-42
40. Koch N, Kahn A, Ghijsen J, Pireaux J J, Schwartz J, Johnson R L and Elschner A 2003 Conjugated organic molecules on metal versus polymer electrodes: demonstration of a key energy level alignment mechanism Appl Phys. Lett. 82 70-2
41. Han W, Yoshida H, Ueno N and Kera S 2013 Electron affinity of pentacene thin film studied by radiation-damage free inverse photoemission spectroscopy Appl. Phys. Lett. 103 123303
42. Willenbockel M, Lüftner D, Stadtmüller B, Koller G, Kumpf C, Soubatch S, Puschnig P, Ramsey M G and Tautz F S 2015 The interplay between interface structure, energy level alignment and chemical bonding strength at organic-metal interfaces Phys. Chem. Chem. Phys. 17 1530-48
43. Heimel G et al 2013 Charged and metallic molecular monolayers through surface-induced aromatic stabilization Nat. Chem. 5 187-94
44. Duhm S, Glowatzki H, Cimpeanu V, Klankermayer J, Rabe J P, Johnson R L and Koch N 2006 Weak charge transfer between an acceptor molecule and metal surfaces enabling organic/metal energy level tuning J. Phys. Chem. B 110 21069-72
45. Bendounan A, Forster F, Schöll A, Batchelor D, Ziroff J, Umbach E and Reinert F 2007 Electronic structure of 1 ML NTCDA/Ag (1 1 1) studied by photoemission spectroscopy Surf. Sci. 601 4013-7
46. Silinsh E and Capek V 1994 Organic Molecular Crystals: Interaction, Localization, and Transport Phenomena (New York: AIP Press)
47. Fukagawa H, Kera S, Kataoka T, Hosoumi S, Watanabe Y, Kudo K and Ueno N 2007 The role of the ionization potential in vacuum-level alignment at organic semiconductor interfaces Adv. Mater. 19 665-8
48. Koch N 2007 Organic electronic devices and their functional interfaces ChemPhysChem 8 1438-55
49. Rhoderick E H and Williams R 1988 Metal-Semiconductor Contacts (Oxford: Clarendon)
50. Ding X M, Hung L M, Cheng L F, Deng Z B, Zhou X Y, Lee C S and Lee S T 2000 Modification of the hole injection barrier in organic light-emitting devices studied by ultraviolet photoelectron spectroscopy Appl. Phys. Lett. 76 2704-6
51. McDonald O, Cafolla A A, Carty D, Sheerin G and Hughes G 2006 Photoemission, NEXAFS and STM studies of pentacene thin films on Au (1 0 0) Surf. Sci. 600 3217-25
52. Yagishita A 2015 Photoelectron angular distributions from single oriented molecules: Past, present and future J. Electron Spectrosc. Relat. Phenom. 200 247-56
53. Tsiper E V and Soos Z G 2003 Electronic polarization in pentacene crystals and thin films Phys. Rev. B 68 085301
54. Duhm S, Heimel G, Salzmann I, Glowatzki H, Johnson R L, Vollmer A, Rabe J P and Koch N 2008 Orientation-dependent ionization energies and interface dipoles in ordered molecular assemblies Nat. Mater. 7 326-32
55. Lo Y-Y, Chang J-H, Hoffmann G, Su W-B, Wu C-I and Chang C-S 2013 A comparative study on the adsorption behavior of pentacene and perfluoropentacene molecules on Au(1 1 1) surfaces Japan. J. Appl. Phys. 52 101601
56. Fukagawa H, Yamane H, Kataoka T, Kera S, Nakamura M, Kudu K and Ueno N 2006 Origin of the highest occupied band position in pentacene films from ultraviolet photoelectron spectroscopy: Hole stabilization versus band dispersion Phys. Rev. B 73 245310
57. Kera S and Ueno N 2015 Photoelectron spectroscopy on the charge reorganization energy and small polaron binding energy of molecular film J. Electron Spectrosc. Relat. Phenom. 204 2-11
58. Yamane H, Nagamatsu S, Fukagawa H, Kera S, Friedlein R, Okudaira K K and Ueno N 2005 Hole-vibration coupling of the highest occupied state in pentacene thin films Phys. Rev. B 72 153412
59. Yoshida H and Sato N 2008 Crystallographic and electronic structures of three different polymorphs of pentacene Phys. Rev. B 77 235205
60. Heimel G, Salzmann I, Duhm S and Koch N 2011 Design of organic semiconductors from molecular electrostatics Chem. Mater. 23 359-77
61. Duhm S, Bürker C, Hosokai T and Gerlach A 2015 Vertical bonding distances impact organic-metal interface energetics Electronic Processes in Organic Electronics (Springer Series in Materials Science vol 209) ed H Ishii et al pp 89-107
62. Romaner L, Heimel G, Brédas J L, Gerlach A, Schreiber F, Johnson R L, Zegenhagen J, Duhm S, Koch N and Zojer E 2007 Impact of bidirectional charge transfer and molecular distortions on the electronic structure of a metal-organic interface Phys. Rev. Lett. 99 256801
63. Duhm S, Gerlach A, Salzmann I, Bröker B, Johnson R L, Schreiber F and Koch N 2008 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. 9 111-8
64. Bürker C, Ferri N, Tkatchenko A, Gerlach A, Niederhausen J, Hosokai T, Duhm S, Zegenhagen J, Koch N and Schreiber F 2013 Exploring the bonding of large hydrocarbons on noble metals: diindoperylene on Cu (1 1 1), Ag (1 1 1), and Au (1 1 1) Phys. Rev. B 87 165443
65. Menozzi C, Corradini V, Cavalini M, Biscarini F, Betti M G and Mariani C 2003 Pentacene self-aggregation at the Au (1 1 0)-(1 × 2) surface: growth morphology and interface electronic states Thin Solid Films 428 227-31
66. Chen Q, McDowall A J and Richardson N 2003 Ordered structures of tetracene and pentacene on Cu (1 1 0) surfaces Langmuir 19 10164-71
67. Wang Y L, Ji W, Shi D X, Du S X, Seidel C, Ma Y G, Gao H J, Chi L F and Fuchs H 2004 Structural evolution of pentacene on a Ag (1 1 0) surface Phys. Rev. B 69 075408
68. Ules T, Lüftner D, Reinisch E M, Koller G, Puschnig P and Ramsey M G 2014 Orbital tomography of hybridized and dispersing molecular overlayers Phys. Rev. B 90 155430
69. Ferretti A, Baldacchini C, Calzolari A, Di Felice R, Ruini A, Molinari E and Betti M G 2007 Mixing of electronic states in pentacene adsorption on copper Phys. Rev. Lett. 99 046802
70. Yamane H, Yoshimura D, Kawabe E, Summi R, Kanai K, Ouchi Y, Ueno N and Seki K 2007 Electronic structure at highly ordered organic/metal interfaces: pentacene on Cu (1 1 0) Phys. Rev. B 76 165436
71. Müller K, Kara A, Kim T K, Bertschiger R, Scheybal A, Osterwalder J and Jung T A 2009 Multimorphism in molecular monolayers: pentacene on Cu (1 1 0) Phys. Rev. B 79 245421
72. Yamane H, Kawabe E, Yoshimura D, Sumii R, Kanai K, Ouchi Y, Ueno N and Seki K 2008 Intermolecular band dispersion in highly ordered monolayer and multilayer filmsw of pentacene on Cu (1 1 0) Phys. Status Solidi b 245 793-8
73. Courths R and Hüfner S 1984 Photoemission experiments on copper Phys. Rep. 112 53-171
74. Duhm S, Salzmann I, Johnson R L and Koch N 2009 Electronic non-equilibrium conditions at C60-pentacene heterostructures J. Electron Spectrosc. Relat. Phenom. 174 40-4
75. Fischer R, Schuppler S, Fischer N, Fauster T H and Steinmann W 1993 Image states and local work function for Ag/Pd (1 1 1) Phys. Rev. Lett. 70 654
76. Duhm S, Salzmann I, Heimel G, Oehzelt M, Haase A, Johnson R L, Rabe J P and Koch N 2009 Controlling energy level offsets in organic/organic heterostructures using intramolecular polar bonds Appl. Phys. Lett. 94 033304
77. Salzmann I, Duhm S, Heimel G, Oehzelt M, Kniprath R, Johnson R L, Rabe J P and Koch N 2008 Tuning the ionization energy of organic semiconductor films: the role of intramolecular polar bonds J. Am. Chem. Soc. 130 12870-1
78. Heimel G, Salzmann I, Duhm S, Rabe J P and Koch N 2009 Intrinsic surface dipoles control the energy levels of conjugated polymers Adv. Funct. Mater. 19 3874-9
79. Kera S, Fukagawa H, Kataoka T, Hosoumi S, Yamane H and Ueno N 2007 Spectroscopic evidence of strong π-π interorbital interaction in a lead-phthalocyanine bilayer film attributed to the dimer nanostructure Phys. Rev. B 75 121305