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Spiro Compounds for Organic Electroluminescence and Related Applications

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Emissive Materials Nanomaterials

Part of the book series: Advances in Polymer Science ((POLYMER,volume 199))

Abstract

A comprehensive review about functional spiro compounds, their synthesis, physical properties and applications in optoelectronic devices is given.

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References

  1. Destriau G (1936) J Chem Phys 33:587

    CAS  Google Scholar 

  2. Holonyak N, Bevacqua SF (1962) Appl Phys Lett 1:82

    CAS  Google Scholar 

  3. Pope M, Kallmann HP, Magnante P (1963) J Chem Phys 38:2042

    CAS  Google Scholar 

  4. Helferich W, Schneider WG (1965) Phys Rev Lett 14:229

    Google Scholar 

  5. Tang CW, Van Slyke SA (1987) Appl Phys Lett 51:913

    CAS  Google Scholar 

  6. Adachi C, Tsutsui T, Tokito S, Saito S (1988) Jpn J Appl Phys 28:L269

    Google Scholar 

  7. Adachi C, Tsutsui T, Saito S (1990) Appl Phys Lett 56:799

    CAS  Google Scholar 

  8. Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burns PL, Holmes AB (1990) Nature 347:539

    CAS  Google Scholar 

  9. Gustavson G, Cao Y, Treacy GM, Klavetter F, Colaneri N, Heeger AJ (1992) Nature 357:477

    Google Scholar 

  10. Kolosov D, English DS, Bulovic V, Barbara PF, Forrest SR, Thompson ME (2001) J Appl Phys 90:3242

    CAS  Google Scholar 

  11. Ke L, Chen P, Chua SJ (2002) Appl Phys Lett 80:697

    CAS  Google Scholar 

  12. McElvain J, Antoniadis H, Hueschen MR, Miller JN, Roitman DM, Scheats JR, Moon RL (1996) J Appl Phys 80:6002

    Google Scholar 

  13. Naito K, Miura A (1993) J Phys Chem 97:6240

    CAS  Google Scholar 

  14. Naito K (1994) Chem Mater 6:2343

    CAS  Google Scholar 

  15. Shirota Y, Kuwabara Y, Okuda D, Okuda R, Ogawa H, Inada H, Wakimoto T, Nakada H, Yonemoto Y, Kawami S, Imai K (1997) J Lumin 72–74:985

    Google Scholar 

  16. Wang S, Oldham WJ, Hudack RA, Bazan GC (2000) J Am Chem Soc 122:5695

    CAS  Google Scholar 

  17. Salbeck J (1996) In: Mauch RH, Gumlich H-E (eds) Inorganic and organic electroluminescence (EL96). Wissenschaft & Technik, Berlin, p 243

    Google Scholar 

  18. Clarkson RG, Gomberg M (1930) J Am Chem Soc 52:2881

    CAS  Google Scholar 

  19. Tour JM, Wu R, Schumm JS, Pearson DL (1996) J Org Chem 61:6906

    Google Scholar 

  20. Sutcliffe FK, Shahidi HM, Patterson D (1978) J Soc Dyers Colour 94:306

    Google Scholar 

  21. Chou C-H, Reddy DS, Shu C-F (2002) J Polym Sci Part A Polym Chem 40:3615

    CAS  Google Scholar 

  22. Poriel C, Ferrand Y, Juillard S, Le Maux P, Simonneaux G (2004) Tetrahedron 60:145

    CAS  Google Scholar 

  23. Weisburger JH, Weisburger EK, Ray FE (1950) J Am Chem Soc 72:4253

    CAS  Google Scholar 

  24. Prelog V, Bedekovic D (1979) Helv Chim Acta 62:2285

    CAS  Google Scholar 

  25. Prelog V, Haas G (1969) Helv Chim Acta 52:1202

    Google Scholar 

  26. Mattiello L, Fioravanti G (2001) Synth Commun 31:2645

    CAS  Google Scholar 

  27. Yu W-L, Pei J, Huang W, Heeger AJ (2000) Adv Mater 12:828

    CAS  Google Scholar 

  28. Pei J, Ni J, Zhou XH, Cao XY, Lai YH (2002) J Org Chem 67:4924

    CAS  Google Scholar 

  29. Wu F-I, Rajasekhar D, Reddy DS, Shu C-F (2002) J Mater Chem 12:2893

    CAS  Google Scholar 

  30. Moore JS, Weinstein EJ, Wu Z (1991) Tetrahedron Lett 32:2465

    CAS  Google Scholar 

  31. Tour JM, Wu R, Schumm JS (1990) J Am Chem Soc 112:5662

    CAS  Google Scholar 

  32. Weissörtel F (1999) Synthese und Charakterisierung spiroverknüpfter niedermolekularer Gläser für optoelektronische Anwendungen. Universität Regensburg

    Google Scholar 

  33. Lützen A, Thiemann F, Meyer S (2002) Synthesis 2771

    Google Scholar 

  34. Wu X-m, Chen X-c, Cao X-p, Pan X-f (2001) Ganguang Kexue Yu Guang Huaxue 19:161

    Google Scholar 

  35. Merkushev EB (1988) Synthesis 923

    Google Scholar 

  36. Lee H, Oh J, Chu HY, Lee J-I, Kim SH, Yang YS, Kim GH, Do L-M, Zyung T, Lee J, Park Y (2003) Tetrahedron 59:2773

    CAS  Google Scholar 

  37. Kim Y-H, Shin D-C, Kim S-H, Ko C-H, Yu H-S, Chae Y-S, Kwon S-K (2001) Adv Mater 13:1690

    CAS  Google Scholar 

  38. Treacher K, Becker H, Stoessel P, Spreitzer H, Falcou A, Parham A, Buesing A (2002) PCT Int Appl (Covion Organic Semiconductors GmbH, Germany), WO 02077060

    Google Scholar 

  39. Stoessel P, Spreitzer H, Becker H, Drott J (2002) PCT Int Appl (Covion Organic Semiconductors GmbH, Germany), WO 02051850

    Google Scholar 

  40. Hung LS, Tang CW, Mason MG (1997) Appl Phys Lett 71:1762

    Google Scholar 

  41. Shaheen SE, Jabbour GE, Morrell MM, Kawabe Y, Kippelen B, Peyghambarian N, Nabor MF, Schlaf R, Mash EA, Armstrong NR (1998) J Appl Phys 84:2324

    CAS  Google Scholar 

  42. Brown TM, Friend RH, Millard IS, Lacey DJ, Burroughes JH, Cacialli F (2000) Appl Phys Lett 77:3096

    CAS  Google Scholar 

  43. Furukawa K, Terasaka Y, Ueda H, Matsumura M (1997) Synth Met 91:99

    CAS  Google Scholar 

  44. Nuesch F, Forsythe EW, Lee QT, Gao Y, Rothberg LJ (2000) J Appl Phys 87:7973

    CAS  Google Scholar 

  45. Van Slyke SA, Chen CH, Tang CW (1996) Appl Phys Lett 69:2160

    Google Scholar 

  46. Carter SA, Angelopoulos M (1997) Appl Phys Lett 70:2067

    CAS  Google Scholar 

  47. Aminaka E, Tsutsui T, Saito S (1996) J Appl Phys 79:8808

    CAS  Google Scholar 

  48. Yeh P (1988) Optical waves in layered media. Wiley, New York

    Google Scholar 

  49. McGehee MD, Gupta R, Veenstra S, Miller EK, Diaz-Garcia MA, Heeger AJ (1998) Phys Rev B 58:7035

    CAS  Google Scholar 

  50. Salbeck J, Schörner M, Fuhrmann T (2002) Thin Solid Films 417:20

    CAS  Google Scholar 

  51. Heinze J (1984) Angew Chem 96:823

    CAS  Google Scholar 

  52. Ishii H, Sugiyama K, Ito E, Seki K (1999) Adv Mater 11:605

    CAS  Google Scholar 

  53. Bard AJ, Faulkner LR (2001) Electrochemical methods, fundamentals and applications. Wiley, New York

    Google Scholar 

  54. Pommerehne J, Westweber H, Guss W, Mahrt RF, Bässler H, Porsch M, Daub J (1995) Adv Mater 7:551

    CAS  Google Scholar 

  55. Horowitz G (2000) In: Hadziioannou G, van Hutten PF (eds) Semiconducting polymers. Chemistry, Physics and Engineering. Wiley, Weinheim, p 463

    Google Scholar 

  56. Nelson SF, Lin Y-Y, Gundlach J, Jackson TN (1998) Appl Phys Lett 72:1854

    CAS  Google Scholar 

  57. Katz HE, Lovinger AJ, Johnson J, Kloc C, Siegrist T, Li W, Lin Y-Y, Dodabalapur A (2000) Nature 404:478

    CAS  Google Scholar 

  58. Adam D, Schumacher P, Simmerer J, Häußling L, Siemensmeyer K, Etzbach K-H, Ringsdorf H, Haarer D (1994) Nature 371:141

    CAS  Google Scholar 

  59. Bässler H (1993) Phys Stat Sol (b) 175:15

    Google Scholar 

  60. Facci JS, Stolka M (1986) Philos Mag B 54:1

    CAS  Google Scholar 

  61. Stephan J, Schrader S, Brehmer L (2000) Synth Met 111:353

    Google Scholar 

  62. Brown AR, Jarrett CP, de Leeuw DM, Matters M (1997) Synth Met 88:37

    CAS  Google Scholar 

  63. Borsenberger PM, Weiss DS (1993) Organic photoreceptors for imaging systems. Marcel Dekker, New York

    Google Scholar 

  64. Forrest SR, Bradley DDC, Thompson ME (2003) Adv Mater 15:1043

    CAS  Google Scholar 

  65. American Society for Testing and Materials (1998) G159–198

    Google Scholar 

  66. Brabec CJ, Sariciftci NS (2000) In: Hadzioannou G, van Hutten PF (eds) Semiconducting polymers. Wiley, Weinheim, p 528

    Google Scholar 

  67. Wirth HO (1961) In: Proceedings of the International Conference on Luminescence of organic and inorganic materials. New York, p 226

    Google Scholar 

  68. Wirth HO, Herrmann FU, Herrmann G, Kern W (1968) Mol Cryst 4:321

    Google Scholar 

  69. Ried W, Freitag D (1968) Angew Chem 80:932

    Google Scholar 

  70. Salbeck J (1996) Ber Bunsen-Ges Phys Chem Chem Phys 100:1667

    CAS  Google Scholar 

  71. Salbeck J, Weissortel F, Bauer J (1997) Macromol Symp 125:121

    Google Scholar 

  72. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    CAS  Google Scholar 

  73. Salbeck J, Weinfurthner K-H, Weissörtel F, Harmgarth G (1998) Proc SPIE 3476:40

    Google Scholar 

  74. Minato A, Tamao K, Hayashi T, Suzuki K, Kumada M (1980) Tetrahedron Lett 21:845

    CAS  Google Scholar 

  75. Shen W-J, Dodda R, Wu C-C, Wu F-I, Liu T-H, Chen H-H, Chen CH, Shu C-F (2004) Chem Mater 16:930

    CAS  Google Scholar 

  76. Wu C-C, Liu T-L, Hung W-Y, Lin Y-T, Wong K-T, Chen R-T, Chen Y-M, Chien Y-Y (2003) J Am Chem Soc 125:3710

    CAS  Google Scholar 

  77. Wong K-T, Chien Y-Y, Chen R-T, Wang C-F, Lin Y-T, Chiang H-H, Hsieh P-Y, Wu C-C, Chou HC, Yuhlong OS, Lee G-H, Peng S-M (2002) J Am Chem Soc 124:11576

    CAS  Google Scholar 

  78. Davydov AS (1948) 18:515

    Google Scholar 

  79. Berlman IB (1968) Mol Cryst 4:157

    Google Scholar 

  80. Brackmann U (2000) Lambdachrome Laser Dyes. Lambda Physik, Goettingen

    Google Scholar 

  81. Johansson N, dos Santos DA, Guo S, Cornil J, Fahlman M, Salbeck J, Schenk H, Arwin H, Bredas JL, Salanek WR (1997) J Chem Phys 107:2542

    CAS  Google Scholar 

  82. Milota F (1999) Master Thesis, University of Vienna

    Google Scholar 

  83. Milota F, Warmuth C, Tortschanoff A, Sperling J, Fuhrmann T, Salbeck J, Kauffmann HF (2001) Synth Met 121:1497

    CAS  Google Scholar 

  84. Birks JB (1970) Photophysics of aromatic molecules. Wiley, London

    Google Scholar 

  85. Berlman IA (1971) Handbook of fluorescence spectra of aromatic molecules. Academic, New York

    Google Scholar 

  86. Geng Y, Katsis D, Culligan SW, Ou JJ, Chen SH, Rothberg LJ (2002) Chem Mater 14:463

    CAS  Google Scholar 

  87. Katsis D, Geng YH, Ou JJ, Culligan SW, Trajkovska A, Chen SH, Rothberg LJ (2002) Chem Mater 14:463

    Google Scholar 

  88. Schartel B, Damerau T, Hennecke M (2000) Phys Chem Chem Phys 2:4690

    CAS  Google Scholar 

  89. Schörner M (2000) Master's thesis, Kassel University, Germany

    Google Scholar 

  90. Johansson N, Salbeck J, Bauer J, Weissortel F, Broms P, Andersson A, Salaneck WR (1998) Adv Mater 10:1136

    CAS  Google Scholar 

  91. Spehr T, Pudzich R, Fuhrmann T, Salbeck J (2003) Org Electron 4:61

    Google Scholar 

  92. Benstem T (2002) Lumineszenz-Dynamik und stimulierte Emission von organischen Dünnschichten. Cuvillier, Göttingen

    Google Scholar 

  93. Wong K-T, Chien Y-Y, Chen R-T, Wang C-F, Lin Y-T, Chiang H-H, Hsieh P-Y, Wu C-C, Chou HC, Yuhlong OS, Lee G-H, Peng S-M (2002) J Am Chem Soc 124:11576

    CAS  Google Scholar 

  94. Crispin A, Crispin X, Fahlman M, dos Santos DA, Cornil J, Johansson N, Bauer J, Weissortel F, Salbeck J, Bredas JL, Salaneck WR (2002) J Chem Phys 116:8159

    CAS  Google Scholar 

  95. Salbeck J, Yu N, Bauer J, Weissortel F, Bestgen H (1997) Synth Met 91:209

    CAS  Google Scholar 

  96. Steuber F, Staudigel J, Stossel M, Simmerer J, Winnacker A, Spreitzer H, Weissortel F, Salbeck J (2000) Adv Mater 12:130

    CAS  Google Scholar 

  97. Salbeck J, Spreitzer H, Schenk H, Weissortel F, Riel H, Riess W (1999) Proc SPIE 3797:316

    Google Scholar 

  98. Chun C, Kim M-J, Vak D, Kim DY (2003) J Mater Chem 13:2904

    CAS  Google Scholar 

  99. Fuhrmann T, Tsutsui T (1999) Chem Mater 11:2226

    CAS  Google Scholar 

  100. Hosokawa C, Higashi H, Nakamura H, Kusumoto T (1995) Appl Phys Lett 67:3853

    CAS  Google Scholar 

  101. Rochon P, Batalla E, Natansohn A (1995) Appl Phys Lett 66:136

    CAS  Google Scholar 

  102. Kim DY, Li L, Kumar J, Tripathy SK (1995) Appl Phys Lett 66:1166

    CAS  Google Scholar 

  103. Hartwig JF (1998) Angew Chem 110:2154

    Google Scholar 

  104. Gauthier S, Fréchet JM (1987) Synthesis 383

    Google Scholar 

  105. Fujikawa H, Tokito S, Taga Y (1997) Synth Met 91:161

    CAS  Google Scholar 

  106. Anderson JD, McDonald EM, Lee PA, Anderson ML, Ritchie EL, Hall HK, Hopkins T, Mash EA, Wang J, Padias A, Tayumanavan S, Barlow S, Marder SR, Jabbour GE, Shaheen S, Kippelen B, Peyghambarian N, Whightman RM, Armstrong NR (1998) J Am Chem Soc 120:9646

    CAS  Google Scholar 

  107. Shirota Y (2000) J Mater Chem 10:1

    CAS  Google Scholar 

  108. Kanai H, Ichinosawa S, Sato Y (1997) Synth Met 91:195

    CAS  Google Scholar 

  109. Heun S, Borsenberger PM (1995) Chem Phys 200:245

    CAS  Google Scholar 

  110. Bach U, De Cloedt K, Spreitzer H, Grätzel M (2000) Adv Mater 12:1060

    CAS  Google Scholar 

  111. Poplavskyy D, Nelson J (2003) J Appl Phys 93:341

    CAS  Google Scholar 

  112. Saragi TPI, Pudzich R, Fuhrmann T, Salbeck J (2002) MRS Proc 725:85

    Google Scholar 

  113. Saragi TPI, Fuhrmann-Lieker T, Salbeck J (2005) Synth Met 148:267

    CAS  Google Scholar 

  114. Huang J, Pfeiffer M, Blochwitz J, Werner A, Salbeck J, Liu S, Leo K (2001) Jpn J Appl Phys 40:6630

    CAS  Google Scholar 

  115. O'Regan B, Grätzel M (1991) Nature 353:737

    Google Scholar 

  116. Bach U, Lupo D, Comte P, Moser JE, Weissortel F, Salbeck J, Spreitzer H, Gratzel M (1998) Nature 395:583

    CAS  Google Scholar 

  117. Krüger J, Plass R, Cevey L, Piccirelli M, Grätzel M (2001) Appl Phys Lett 79:2085

    Google Scholar 

  118. Stanforth SP (1998) Tetrahedron 54:263

    CAS  Google Scholar 

  119. Tour JM (1994) Adv Mater 6:190

    CAS  Google Scholar 

  120. Aviram A (1988) J Am Chem Soc 110:5687

    CAS  Google Scholar 

  121. Pei J, Ni J, Zhou X-H, Cao X-Y, Lai Y-H (2002) J Org Chem 67:8104

    CAS  Google Scholar 

  122. Mitschke U, Bäuerle P (2001) J Chem Soc Perkin Trans 1:740

    Google Scholar 

  123. Ong T-T, Ng S-C, Chan HSO, Vardhanan RV, Kumura K, Mazaki Y, Kobayashi K (2003) J Mater Chem 13:2185

    CAS  Google Scholar 

  124. van Pham C, Burckhardt A, Shabana R et al. (1989) Phosphor Sulfur Silicon 46:153

    Google Scholar 

  125. Becker RS, Melo JSD, Macanita AL, Elisei F (1995) Pure Appl Chem 67:9

    CAS  Google Scholar 

  126. Bäuerle P, Mitschke U, Mena-Osteritz E, Sokolowski M, Müller D, Groß M, Meerholz K (1998) Proc SPIE 3476:32

    Google Scholar 

  127. Huisgen R (1963) Angew Chem 75:604

    CAS  Google Scholar 

  128. Huisgen R, Seidl H (1965) Chem Ber 98:2966

    Google Scholar 

  129. Brown HC, Kassal RJ (1967) J Org Chem 32:1871

    CAS  Google Scholar 

  130. Wu CC, Lin YT, Chiang HH, Cho TY, Chen CW, Wong KT, Liao YL, Lee GH, Peng SM (2002) Appl Phys Lett 81:577

    CAS  Google Scholar 

  131. Wu F, Riesgo EC, Thummel RP, Juris A, Hissler M, El-ghayoury A, Ziessel R (1999) Tetrahedron Lett 40:7311

    CAS  Google Scholar 

  132. Juris A, Prodi L, Harriman A, Ziessel R, Hissler M, El-ghayoury A, Wu F, Riesgo EC, Thummel RP (2000) Inorg Chem 39:3590

    CAS  Google Scholar 

  133. Poriel C, Ferrand Y, Le Maux P, Raul-Berthelot J, Simonneaux G (2003) Chem Commun 1104

    Google Scholar 

  134. Poriel C, Ferrand Y, Le Maux P, Rault-Berthelot J, Simonneaux G (2003) Tetrahedron Lett 44:1759

    CAS  Google Scholar 

  135. Maeda M (1984) Laser Dyes. Academic, Orlando, FL

    Google Scholar 

  136. Pudzich R, Salbeck J (2003) Synth Met 138:21

    CAS  Google Scholar 

  137. Diederich F, Alcazar V, Moran JR (1992) Isr J Chem 32:69

    Google Scholar 

  138. Hetzheim A (1994) Houben-Weyl, Methoden der organischen Chemie (Houben-Weyl, Methoden der organischen Chemie), vol E8c. Georg Thieme, Stuttgart, p 525

    Google Scholar 

  139. Hartwig JF (1998) Angew Chem-Int Edit Engl 37:2046

    CAS  Google Scholar 

  140. Pudzich R (2002) Synthese und Charakterisierung spiroverknüpfter Emitter- und Ladungstransportmaterialien mit kombinierten Funktionalitäten. PhD thesis, Universität Kassel, Germany

    Google Scholar 

  141. Chien Y-Y, Wong K-T, Chou P-T, Cheng Y-M (2002) Chem Commun 2874

    Google Scholar 

  142. Maslak P, Chopra A, Moylan CR, Wortmann R, Lebus S, Rheingold AL, Yap GPA (1996) J Am Chem Soc 118:1471

    CAS  Google Scholar 

  143. Maslak P (1994) Adv Mater 6:405

    CAS  Google Scholar 

  144. Maslak P, Chopra A (1993) J Am Chem Soc 115:9331

    CAS  Google Scholar 

  145. Maslak P, Augustine MP, Burkey JD (1990) J Am Chem Soc 112:5359

    CAS  Google Scholar 

  146. Saragi TPI, Pudzich R, Fuhrmann T, Salbeck J (2004) Appl Phys Lett 84:2334

    CAS  Google Scholar 

  147. Harada N, Ono H, Nishiwaki T, Uda H (1991) J Chem Soc Chem Commun 1753

    Google Scholar 

  148. Alcazar V, Diederich F (1992) Angew Chem 104:1503

    CAS  Google Scholar 

  149. Cuntze J, Diederich F (1997) Helv Chim Acta 80:897

    CAS  Google Scholar 

  150. Dantzig NA, Levy DH, Vigo C, Piotrowiak P (1995) J Chem Phys 103:4894

    Google Scholar 

  151. Shain AL, Ackerman JP, Teague MW (1969) Chem Phys Lett 3:550

    CAS  Google Scholar 

  152. Schweig A, Weidner U, Hellwinkel D, Krapp W (1973) Angew Chem 85:360

    CAS  Google Scholar 

  153. Kreuder W, Lupo D, Salbeck J, Schenk H, Stehlin T (1997) US Patent, US5621131

    Google Scholar 

  154. Wu S-C, Shu C-F (2003) J Polym Sci Part A Polym Chem 41:1160

    CAS  Google Scholar 

  155. Chiang C-L, Shu C-F (2002) Chem Mater 14:682

    CAS  Google Scholar 

  156. Müller CD, Falcou A, Reckefuss N, Rojahn M, Wiederhirn V, Rudati P, Frohne H, Nuyken O, Becker H, Meerholz K (2003) Nature 421:829

    Google Scholar 

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Pudzich, R., Fuhrmann-Lieker, T., Salbeck, J. (2006 ). Spiro Compounds for Organic Electroluminescence and Related Applications. In: Emissive Materials Nanomaterials. Advances in Polymer Science, vol 199. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_074

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