journal article·2008-08-01

Air-Stable, Cross-Linkable, Hole-Injecting/Transporting Interlayers for Improved Charge Injection in Organic Light-Emitting Diodes

Jianfeng Li, Tobin J. Marks

Chemistry of Materials· Volume 20· Issue 15
Publisher page

Abstract

Modification of inorganic electrode surfaces has attracted great attention in the quest to optimize organic optoelectronic devices. An air-stable, cross-linkable trimethoxysilane functionalized hole-transporting triarylamine (4,4′-bis[( p -trimethoxysilylpropylphenyl)phenylamino]biphenyl, TPD−[Si(OMe) 3 ] 2 ) has been synthesized and self-assembled or spin-coated onto tin-doped indium oxide (ITO) anode surfaces to form monolayers or multilayer siloxane films, respectively. The modified ITO surfaces were characterized by advancing aqueous contact angle, X-ray photoelectron spectroscopy (XPS), atomic force microscopy (AFM), and cyclic voltammetry (CV). Increased surface work function and enhanced ITO−hole transport layer (HTL) contact via robust covalent bonding are expected to facilitate hole injection from the ITO anode, resulting in organic light-emitting diode (OLED) performance enhancement versus that of a device without such interlayers. For a device having the structure ITO/spin-coated-TPD−[Si(OMe) 3 ] 2 from aqueous alcohol + acetic acid blend solution (40 nm)/NPB (20 nm)/Alq (60 nm)/LiF (1 nm)/Al (100 nm), a maximum light output of 32 800 cd/m 2, a 4.25 V turn-on voltage, and a maximum current efficiency of 5.8 cd/A is achieved. This performance is comparable to or superior to that of analogous devices prepared with analogous trichorosilyl precursors. The air-stable interlayer material developed here is also applicable to large-area coating techniques.
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Research context

OpenAlex topics: Organic Light-Emitting Diodes Research · Molecular Junctions and Nanostructures · Organic Electronics and Photovoltaics

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208

References (72)

Show source-provided references
1. Martin, G. InHandbook of Optoelectronics;Dakin, J. P., Brown, R. G. W., Eds.CRC Press LLC:Boca Raton, FL,2006; Vol.II, Chapter 1, pp693−718.
2. Veinot J. G. C. · Acc. Chem. Res. · 2005 · 38 · 63210.1021/ar030210r ↗
3. Chen C.-T. · Chem. Mater. · 2004 · 16 · 438910.1021/cm049679m ↗
4. Shim H.-K. · Adv. Polym. Sci. · 2002 · 158 · 19310.1007/3-540-44608-7_4 ↗
5. Nalwa, H. S.InHandbook of Advanced Electronic and Photonic Materials and Devices;Nalwa, H. S., Ed.Academic:San Diego, CA,2001;Vol.10, pp1−51.
6. Mitschke U. · J. Mater. Chem. · 2000 · 10 · 147110.1039/a908713c ↗
7. Scherf U. · Adv. Mater. · 2002 · 14 · 47710.1002/1521-4095(20020404)14:7<477::AID-ADMA477>3.0.CO;2-9 ↗
8. Huang Q. · J. Appl. Phys. · 2007 · 101 · 093101/01
9. Huang Q. · Chem. Mater. · 2006 · 18 · 243110.1021/cm0604918 ↗
10. Huang Q. · J. Am. Chem. Soc. · 2005 · 127 · 1022710.1021/ja051077w ↗
11. Huang Q. · J. Am. Chem. Soc. · 2003 · 125 · 1470410.1021/ja037174b ↗
12. Huang Q. L. · Appl. Phys. Lett. · 2003 · 82 · 33110.1063/1.1536268 ↗
13. Niu Y. H. · Appl. Phys. Lett. · 2003 · 82 · 216310.1063/1.1564875 ↗
14. Duan J. P. · Adv. Mater. · 2003 · 15 · 22410.1002/adma.200390051 ↗
15. Müller C. D. · Nature · 2003 · 421 · 82910.1038/nature01390 ↗
16. Niu Y. H. · Appl. Phys. Lett. · 2002 · 81 · 288410.1063/1.1510581 ↗
17. Herguch P. · Macromolecules · 2002 · 35 · 609410.1021/ma020405z ↗
18. Ishii H. · Adv. Mater. · 1999 · 11 · 60510.1002/(SICI)1521-4095(199906)11:8<605::AID-ADMA605>3.0.CO;2-Q ↗
19. Tang C. W. · Appl. Phys. Lett. · 1987 · 51 · 91310.1063/1.98799 ↗
20. Brown A. R. · Appl. Phys. Lett. · 1992 · 61 · 279310.1063/1.108094 ↗
21. Shen Y. · Adv. Mater. · 2001 · 13 · 123410.1002/1521-4095(200108)13:16<1234::AID-ADMA1234>3.0.CO;2-R ↗
22. Forsythe E. W. · J. Phys. Chem. B · 2000 · 104 · 394810.1021/jp993793o ↗
23. Nesch F. · J. Appl. Phys. · 2000 · 87 · 797310.1063/1.373482 ↗
24. Appleyard S. F. J. · J. Mater. Chem. · 2000 · 10 · 16910.1039/a903708j ↗
25. Malinsky J. E. · Adv. Mater. · 1999 · 11 · 22710.1002/(SICI)1521-4095(199903)11:3<227::AID-ADMA227>3.0.CO;2-3 ↗
26. Hatton R. A. · J. Mater. Chem. · 2003 · 13 · 72210.1039/b211775b ↗
27. Lee J. · J. Mater. Chem. · 2002 · 12 · 349410.1039/B206939C ↗
28. Gross M. · Nature · 2000 · 405 · 66110.1038/35015037 ↗
29. Yang Y. · Appl. Phy. Lett. · 1994 · 64 · 124510.1063/1.110853 ↗
30. Carter S. A. · Appl. Phys. Lett. · 1997 · 70 · 206710.1063/1.118953 ↗
31. Brown T. M. · Appl. Phys. Lett. · 1999 · 75 · 167910.1063/1.124789 ↗
32. Groenendaal B. L. · Adv. Mater. · 2000 · 12 · 48110.1002/(SICI)1521-4095(200004)12:7<481::AID-ADMA481>3.0.CO;2-C ↗
33. Cao Y. · Synth. Met. · 1997 · 87 · 17110.1016/S0379-6779(97)03823-X ↗
34. Tadayyon S. M. · Org. Electron. · 2004 · 5 · 15710.1016/j.orgel.2003.10.001 ↗
35. Mori T. · Appl. Phys. Lett. · 2002 · 80 · 389510.1063/1.1481540 ↗
36. Appleyard S. F. J. · J. Mater. Chem. · 2000 · 10 · 16910.1039/a903708j ↗
37. Guo J. · J. Phys. Chem. B · 2005 · 109 · 396610.1021/jp046337v ↗
38. Berlin A. · J. Am. Chem. Soc. · 1998 · 120 · 1345310.1021/ja9824728 ↗
39. Shen Y. · Adv. Mater. · 2001 · 13 · 123410.1002/1521-4095(200108)13:16<1234::AID-ADMA1234>3.0.CO;2-R ↗
40. Ganzorig C. · Appl. Phys. Lett. · 2001 · 79 · 27210.1063/1.1384896 ↗
41. Bruening M. · J. Am. Chem. Soc. · 1994 · 116 · 297210.1021/ja00086a029 ↗
42. Malinsky J. E. · Adv. Mater. · 1999 · 11 · 22710.1002/(SICI)1521-4095(199903)11:3<227::AID-ADMA227>3.0.CO;2-3 ↗
43. Cui J. · Langmuir · 2001 · 17 · 205110.1021/la010158c ↗
44. Cui J. · Langmuir · 2002 · 18 · 995810.1021/la020481v ↗
45. Milliron D. J. · J. Appl. Phys. · 2000 · 87 · 57210.1063/1.371901 ↗
46. Li W. · Adv. Mater. · 1999 · 11 · 73010.1002/(SICI)1521-4095(199906)11:9<730::AID-ADMA730>3.0.CO;2-T ↗
47. Cui J. · Adv. Mater. · 2002 · 14 · 56510.1002/1521-4095(20020418)14:8<565::AID-ADMA565>3.0.CO;2-3 ↗
48. Huang Q. L. · Appl. Phys. Lett. · 2002 · 81 · 352810.1063/1.1517397 ↗
49. Yan H. · Adv. Mater. · 2003 · 15 · 83510.1002/adma.200304585 ↗
50. Yan H. · Appl. Phys. Lett. · 2004 · 84 · 387310.1063/1.1737791 ↗
51. Yan H. · J. Am. Chem. Soc. · 2005 · 127 · 317210.1021/ja044455q ↗
52. Koene B. E. · Chem. Mater. · 1998 · 10 · 223510.1021/cm980186p ↗
53. Ulman A. · Chem. Rev. · 1996 · 96 · 153310.1021/cr9502357 ↗
54. Jeon N. L. · Langmuir · 1995 · 11 · 302410.1021/la00008a029 ↗
55. Ulman A. · Thin Solid Films · 1996 · 273 · 4810.1016/0040-6090(95)06994-1 ↗
56. 2001 · 1
57. Plueddemann E. · 199110.1007/978-1-4899-2070-6 ↗
58. Witucki G. L. · J. Coat. Technol. · 1993 · 65 · 57
59. Crist B. V. · 2004 · 1
60. Grant J. T. · 2003
61. Murray, R. W.InMolecular Design of Electrode Surfaces;Murray, R. W., Ed.Techniques of Chemistry;Wiley:New York,1992; Vol.22, pp1−158.
62. Donley C. · Langmuir · 2002 · 18 · 45010.1021/la011101t ↗
63. DuBois C. J. · J. Electroanal. Chem. · 1998 · 454 · 9910.1016/S0022-0728(98)00255-1 ↗
64. Immoos C. E. · J. Am. Chem. Soc. · 2004 · 126 · 493410.1021/ja038925c ↗
65. Nowall W. B. · Anal. Chem. · 1995 · 67 · 358310.1021/ac00115a031 ↗
66. Inzelt, G.InElectroanalytical Chemistry;Bard, A. J.; Rubenstein, I., Eds.Marcel Dekker:New York,1994;Vol.18, pp90−134.
67. Napper A. M. · J. Phys. Chem. B · 2001 · 105 · 769910.1021/jp0105140 ↗
68. Nahir T. M. · Anal. Chem. · 1994 · 66 · 259510.1021/ac00087a027 ↗
69. Forster R. J. · Inorg. Chem. · 1996 · 35 · 339410.1021/ic951343e ↗
70. Richardson J. N. · Electrochim. Acta · 1995 · 40 · 133110.1016/0013-4686(95)00068-P ↗
71. Cahen D. · Adv. Mater. · 2002 · 14 · 78910.1002/1521-4095(20020605)14:11<789::AID-ADMA789>3.0.CO;2-H ↗
72. Yan H. · Adv. Mater. · 2004 · 16 · 194810.1002/adma.200400627 ↗