Skip to main content

Nanoscopically Engineered Polyimides

  • Chapter
  • First Online:
Macromolecular Architectures

Part of the book series: Advances in Polymer Science ((POLYMER,volume 147))

Abstract

Polyimides are currently the materials of choice for interlayer dielectrics in microelectronic applications, since polyimides, as a class of materials, best satisfy the requisite properties to survive the thermal, chemical, and mechanical stresses associated with microelectronic fabrication. As more function is demanded of these polymer dielectrics, e.g., low residual thermal stress, adhesion, photosensitivity, and low dielectric constant, it becomes increasingly difficult to design materials with the desired enhancements without compromising existing properties. This article will describe an approach to modify polyimide with minimal sacrifice to its desirable properties. The preparation of block and graft copolymers provides a means of tailoring the morphology and properties of polyimide through the judicious choice of the coblock, coblock composition, molecular architecture, and block lengths. It is the advent of the poly(amic alkyl ester) intermediate to the polyimide that allows for the controlled synthesis of such block copolymers. The hydrolytic stability of the poly(amic alkyl ester) precursor allows for the isolation and characterization of the copolymers prior to imidization. Such systems represent self-assembling arrays with considerable potential for the preparation of nanostructures, and this article will describe the modification of rigid and semi-rigid polyimides through copolymerization to address favorably such issues as residual thermal stress, dielectric constant, auto-adhesion, and other key design criteria.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Tummala RR, Rymaszewski EJ (1989) Microelectronics packaging handbook. Van Nostrand Reinhold, New York, Chap 1

    Google Scholar 

  2. Hedrick JL, Brown HR, Volksen W, Sanchez M, Plummer CJG, Hilborn JG (1997) Polymer, 38: 605

    Article  CAS  Google Scholar 

  3. Brown HR, Yan ACM, Russel TP, Volksen W, Kramer EJ (1988) Polymer 29:1807

    Article  CAS  Google Scholar 

  4. Numata S, Fujisaki K, Makino D, Kinjo N (1985) Proceedings of the 2nd Technical Conference on Polyimides: Society of Plastic Engineers. Ellenville, New York, p 164

    Google Scholar 

  5. Pfeiffer J, Rhode O (1985) Proceedings of the 2nd Technical Conference on Polyimides: Society of Plastic Engineers. Ellenville, New York, p 336

    Google Scholar 

  6. Cassidy PE (1980) Thermally stable Polymers: Synthesis and properties. Marcel Dekker, New York

    Google Scholar 

  7. Mittal KL(ed) (1984) Polyimides. Plenum Press, New York

    Google Scholar 

  8. Lupinski JH, Moore RS (eds) (1989) Polymeric materials for electronic packaging and interconnection. ACS Symposium Series 407

    Google Scholar 

  9. Takahashi N, Yoon DY, Parrish W (1984) Macromolecules 17: 2583

    Article  CAS  Google Scholar 

  10. Russel TP (1986) J Polym Sci Polym Phys Ed 22: 1105

    Article  Google Scholar 

  11. Gattiglin E, Russel TP (1985) J Polym Sci Part B Polym Phys Ed 27: 2131

    Article  Google Scholar 

  12. Boese D, Lee H, Yoon DY, Swalen JD, Rabolt JF (1992) J Polym Sci Part B Polym Phys Ed 30: 1321

    Article  CAS  Google Scholar 

  13. Volksen W (1994) Adv Polym Sci 117: 111 111

    Google Scholar 

  14. Paraszczak J, Edelstein D, Cohen S, Babich E, Hummel J (1993) IEDM Tech. Digest, p 261

    Google Scholar 

  15. Czornyj G, Chen KR, Prada-Silva G, Arnold A, Souleotis H, Kim S, Ree M, Volksen W, Dawson D, Di Pietro R (1992) 42nd Electronic Components and Technology Conference, p 682

    Google Scholar 

  16. Ree M, Swanson S, Volksen W (1992) Polymer 33:1228

    Article  CAS  Google Scholar 

  17. Chen DH, Chen YP, Arnold CA, Hedrick JC, Graybeal JD, McGrath JE (1989) Int SAMPE Symp 34: 1247

    CAS  Google Scholar 

  18. Musto P, Karasz FE, MacKnight WJ (1989) Polymer 30: 1012

    Article  CAS  Google Scholar 

  19. Guerra G, Choe S, Williams DJ, Karasz FE, MacKnight WJ (1988) Macromolecules 21: 231

    Article  CAS  Google Scholar 

  20. Harris JE, Robeson LM (1986) US Patent 4,609,714 to Union Carbide Corp

    Google Scholar 

  21. Harris JE, Robeson LM (1988) J Appl Polym Sci 35: 1877

    Article  CAS  Google Scholar 

  22. Flory PJ (1978) Macromolecules 11:1138

    Article  CAS  Google Scholar 

  23. Hwang W-F, Wiff DR, Benner CL (1983) J Macromol Sci Phys B 22: 231

    Article  Google Scholar 

  24. Feger C (1989) In Lupinski JH, Moore RJ (eds) Polymeric materials for electronic packaging and interconnection, p 114

    Google Scholar 

  25. Ree M, Yoon DY, Volksen W (1989) PMSE 60: 179

    CAS  Google Scholar 

  26. Yoon DY, Ree M, Volksen W, Hofer D, Depero L, Parrish W (1988) Presented at the Third International Conference on Polyimides, Mid-Hudson Section of SPE, Nov 2-4, Ellenville, New York

    Google Scholar 

  27. Hedrick JL, Labadie JW, Russel TP (1989) In Feger C, Khajastech MM, McGrath JE (eds) Polyimides: Materials, chemistry and characterization. Elsevier Science Publishers, Amsterdam, p 61

    Google Scholar 

  28. Hedrick JL, Hilborn J, Labadie J, Russel TP (1990) Polymer 34: 2384

    Article  Google Scholar 

  29. Haidar M, Chenevey E, Vora RH, Cooper W, Glick A, Jaffe M (1991) Mater Res Soc Symp Proc 227:35

    Google Scholar 

  30. Critchlen JS, Gratan PA, White MA, Pippett J (1972) J Polym Sci A-1 10: 1789

    Google Scholar 

  31. Harris FW, Hsu SLC, Lee CJ, Lee BS, Arnold F, Cheng SZD (1991) Mater Res Soc Symp Proc 227: 3

    CAS  Google Scholar 

  32. Sasaki S, Matuora T, Nishi S, Ando S (1991) Mater Res Soc Symp 227:49

    CAS  Google Scholar 

  33. St Clair AK, St Clair TL, Winfree WP (1988) Proc Amer Chem Soc Div Polym Mater Sci Eng 59: 28

    CAS  Google Scholar 

  34. Chan R, Haasen P, Kramer EJ (eds) (1993) Materials science and technology, vol 12. UCH Weinheim, p 251

    Google Scholar 

  35. Jensen BJ, Hergenrother PM, Bass RG (1989) Proc Polym Mater Sci Eng 60: 294

    CAS  Google Scholar 

  36. Johnson BC, Yilgor I, McGrath JE (1984) Polym Prepr 25(2): 54

    CAS  Google Scholar 

  37. Arnold CA, Sumners JD, Chen YP, Boh DH, McGrath JE (1989) J Polym 30: 986

    Article  CAS  Google Scholar 

  38. Volksen W, Yoon DY, Hedrick JL, Hotopfer D (1991) Mater Res Soc Symp Proc 227:23

    CAS  Google Scholar 

  39. Hergenrother PM (1974) J Appl Polym Sci 18: 1779

    Article  CAS  Google Scholar 

  40. Hergenrother PM (1971) J Macromol Sci Revs Macromol Chem C6: 1

    Google Scholar 

  41. Hedrick JL, Labadie JW (1990) Macromolecules 23:1561

    Article  CAS  Google Scholar 

  42. Labadie JW, Hedrick JL (1992) Die Macromol Chem Macromol Symp Ser 54/55: 313

    CAS  Google Scholar 

  43. Hergenrother P, Connell J, Labadie J, Hedrick JL (1994) Recent advances in heterocycle containing poly(aryl ethers). In Hergenrother PM (ed) High Performance Polymers. Springer-Verlag, Berlin Heidelberg New York

    Google Scholar 

  44. Jurak M, McGrath JE (1989) Polymer 30: 1552

    Article  Google Scholar 

  45. Hedrick JL, Labadie JW, Russel TP (1991) Macromolecules 24:4559

    Article  CAS  Google Scholar 

  46. Labadie JW, Hedrick JL, Boyer S (1992) J Poly Sci Polym Chem Ed 30: 519

    Article  CAS  Google Scholar 

  47. Hedrick JL, Labadie JW (1990) High Performance Polymers 2(1): 3

    CAS  Google Scholar 

  48. Hilborn J, Labadie JW, Hedrick JL (1990) 23: 2854

    Google Scholar 

  49. Hedrick JL (1991) Macromolecules 24: 6361

    Article  CAS  Google Scholar 

  50. Hedrick JL, Hilborn J, Palmer T, Labadie JW, Volksen W (1990) J Poly Sci Polym Chem Ed 28: 2255

    Article  CAS  Google Scholar 

  51. Atwood TE, Barr DA, Faasey GG, Leslie VJ, Newton AB, Rose JB (1977) Polymer 18: 354

    Article  Google Scholar 

  52. Mohanty DK, Lowry RC, Lyle GD, MacGrath JE (1987) Int SAMPE Symp 32:408

    Google Scholar 

  53. Mohanty DK, Senger JS, Smith CD, MacGrath JE (1988) Int SAMPE Symp 33: 970

    CAS  Google Scholar 

  54. Volksen W, Yoon DY, Hedrick JL (1992) IEEE Trans on Components, Hybrids and Manufacturing Technol 15:10

    Google Scholar 

  55. Volksen W, Yoon DY, Hedrick JL, Hofer DC (1992) Mater Res Soc 227: 23

    Google Scholar 

  56. Labadie JW, Hedrick JL (1990) Proc of the 40th Elec Comp and Tech Conf, p 706

    Google Scholar 

  57. Hedrick JL, Labadie JW, Volksen W (1990) Int SAMPE Elec Conf Series 4: 214

    CAS  Google Scholar 

  58. Hedrick JL, Volksen W, Mohanty DK (1991) MRS Symp Ser 227:81;“Polyimides Other High-Temp Polym. Proc Eur Tech Symp (1991) Abadie JJM, Sillion B (eds) Elsevier, Amsterdam, Netherlands

    CAS  Google Scholar 

  59. Hedrick JL, Volksen W, Mohanty DK (1992) J Polym Sci Part A Polym Chem Ed 30: 2085

    Article  CAS  Google Scholar 

  60. Hedrick JL, Volksen W, Mohanty DK (1993) Polym Bull 30: 33

    Article  CAS  Google Scholar 

  61. Russel TP, Brown HR, Grubb DT (1987) J Polym Sci Part A Polym Phys Ed 25: 1129

    Article  Google Scholar 

  62. Labadie JW, Hedrick JL (1990) Macromolecules 23: 5371

    Article  CAS  Google Scholar 

  63. Maxwell-Garnett JC (1905) Phil Trans R Soc 205:237

    Article  Google Scholar 

  64. Gaghani J, Supkis DD (1980) Acta Astronaut 7:653

    Article  Google Scholar 

  65. Smearing RW, Floryan DC (1985) US Patent 4,543,365 to General Electric

    Google Scholar 

  66. Krutchen CM, Wu P (1985) US Patent 4,535,100 to Mobil Oil

    Google Scholar 

  67. Hoki T, Matsuki Y (1986) European Patent 186308 to Aasl Chem

    Google Scholar 

  68. Meyers RA 81969) J Polym Sci Part A-1 7:2757

    Google Scholar 

  69. Carleton PS, Farrissey WJ, Rose JS (1972) J Appl Polym Sci 16: 2983

    Article  CAS  Google Scholar 

  70. Alvino WM, Edelman LE (1975) J Appl Polym Sci 19: 2961

    Article  CAS  Google Scholar 

  71. Farrissey WJ, Rose JS, Carleton PS (1970) J Appl Polym Sci 24:1093

    Article  Google Scholar 

  72. Hammermesh CL, Hogenson PA, Tun CY, Sawako PM, Riccitello R (1979) 11th Natl SAMPE Tech Conf, p 574

    Google Scholar 

  73. Gagliai J (1980) US Patent 4,241,193 to International Harvester

    Google Scholar 

  74. Lee R, Okey DW, Ferro GA (1985) US Patent 4,535,099 to IMI-Tech Corp

    Google Scholar 

  75. Alberino LM (1976) Cell Plast Conf 4:1

    Google Scholar 

  76. Narkis M, Paterman M, Boneh H, Kenig S (1982) Polym Eng Sci 22(7): 417

    Article  CAS  Google Scholar 

  77. McWhirter RJ (1981) Energy Res Abs 6: 2627

    Google Scholar 

  78. McIlroy HM (1977) Energy Res Abs 2: 3469

    Google Scholar 

  79. Gagliani J, Lee R, Sorathin UAK, Wilcoxson AL (1980) Sci Tech Aerosp Rep 18: 37

    Google Scholar 

  80. Gagliani J, Supkis DE (1979) Adv Astronaut Sci 38:193

    CAS  Google Scholar 

  81. Hedrick JL, Charlier Y, Di Pietro R, Jayaraman S, MacGrath JE (1996) J Polym Sci Part A Polym Chem Ed 34: 2867

    Article  CAS  Google Scholar 

  82. Hedrick JL, Di Pietro R, Plummer CJG, Hilborn J, Jerome R (1996) Polymer 37: 5236

    Article  Google Scholar 

  83. Charlier Y, Hedrick JL, Russel TP, Di Pietro R, Jerome R (1995) Polymer 36:4529

    Article  CAS  Google Scholar 

  84. Hedrick JL, Charlier Y, Russel TP, Swanson S, Sanchez M (1995) Polymer 36:1315

    Article  Google Scholar 

  85. Hedrick JL, Di Pietro R, Charlier Y, Jerome R (1995) High performance Polymers 7:133

    Article  Google Scholar 

  86. Hedrick JL, Di Pietro R, Hawker C, Jerome R (1995) Polymer 36:4855

    CAS  Google Scholar 

  87. Hedrick JL, Labadie JW, Russel TP, Hofer D, Wakharkar V (1993) High temperature Polymer foams. Polymer 34:4717

    Article  CAS  Google Scholar 

  88. Labadie JW, Hedrick JL, Wakharkar V, Hofer DC, Russel TP (1992) Proc IEEE Trans-CHMT 15: 925; Proc Electron Compon Technol Conf 42: 688; Hedrick JL, Di Pietro R, Plummer CJG, Hilborn J, Jerome R (1995) Polymer 36: 2485

    CAS  Google Scholar 

  89. Charlier Y, Hedrick JL, Russel TP, Volksen W (1994) Polymer 34:4717

    Google Scholar 

  90. Hedrick JL, Russel TP, Lucas M, Labadie J, Swanson S (1995) Polymer 36: 987

    Article  Google Scholar 

  91. Rogers ME, Moy TM, Kim YS, MacGrath JE (1992) Mat Plas Soc Symp 13: 264

    Google Scholar 

  92. Patel N (1990) Multicomponent network and linear Polymer system: Thermal and morphological characterization. PhD dissertation, U.P.I. + S.U. (under MacGrath JE)

    Google Scholar 

  93. Bywater S, Black PE (1965) J Phys Chem 69: 2967

    Article  CAS  Google Scholar 

  94. Sinaha R, Wall LA, Bram T (1958) J Chem Phys 29: 894

    Article  Google Scholar 

  95. Trollsås M, Hedrick JL, Mecerreyes, Dubois P, Jérôme R, Ihre H, Hult A (199/9 Macromolecules 30: 8608

    Google Scholar 

  96. Hedrick JL, Carter KR, Flores U, Miller RD, Russel TP, Mecerreyes D, Jérôme R (1998) Chem. of Mater. 10:39

    Article  CAS  Google Scholar 

  97. Trollsås M, Hedrick JL, Mecerreyes D, Dubois P, Jérôme R, Ihre H, Hult A (1998) Macromolecules 31: 2756

    Article  CAS  Google Scholar 

  98. Hawker CJ, Hedrick JL (1995) Macromolecules 28: 2993

    Article  CAS  Google Scholar 

  99. Hedrick JL, Miller RD, Hawker CJ, Carter KR, Volksen W, Yoon DY, Trollsås M (1998)Adv. Mater. 10: v

    Article  Google Scholar 

  100. Sanchez M, Hedrick JL, Russel TP (1995) J Polym Sci Phys Ed 33: 253

    Article  Google Scholar 

  101. Plummer CJG, Hedrick JL, Hilborn JG (1995) Polymer 36: 2485

    Article  CAS  Google Scholar 

  102. Cha HJ, Hedrick JL, Di Pietro RA, Blume T, Beyers R, Yoon DY (1996) Appl Phys Lett 68:1

    Article  Google Scholar 

  103. Volksen W, Hedrick JL, Russel TP, Swanson S (1997) J. Applied Polym Sci 66:195

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1999 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Hedrick, J.L., Labadie, J.W., Volksen, W., Hilborn, J.G. (1999). Nanoscopically Engineered Polyimides. In: Hilborn, J.G., et al. Macromolecular Architectures. Advances in Polymer Science, vol 147. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-49196-1_2

Download citation

  • DOI: https://doi.org/10.1007/3-540-49196-1_2

  • Received:

  • Published:

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-65576-3

  • Online ISBN: 978-3-540-49196-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics