US0057831  l 1A  United  States  Patent  [19]  Ikkala  et al.  [111  Patent  Number:  5,783,111  [451  Date  of  Patent:  Jul.  21,  1998  [54]  ELECTRICALLY  CONDUCTING  COMPOSITIONS  [75]  Inventors:  Olli  lkkala.  Merikasannink:atu;  Lars-Olof  Pietila.  Purismiehenkatu.  both  of  Finland;  Yong Cao.  Goleta;  Alejandro  Andreatta,  Santa  Barbara.  both  of  Calif.  [73]  Assignees:  Uniax  Corporation,  Santa  Barbara,  Calif.;  Neste  Oy,  Espoo.  Finland  [21]  Appl.  No.:  582,809  [22]  Filed:  Jan.  4, 1996  [63]  Continuation-in-part  of Ser.  No.  549,557,  Oct.  27, 1995,  abandoned,  which  is  a  continuation  of Ser.  No.  115,536,  Sep.  3,  1993,  abandoned.  [51]  Int.  Cl.  6  .......................................................  H0IB  1/12  [52]  U.S.  Cl.  ..............................................................  252/500  [58]  Field of  Search  .....................................  252/500.  518.  252/519;  528/422  Related  U.S.  Application  Data  [56]  References  Cited  U.S.  PPJENf  DOCUMENfS  3,963,498  4,025,463  4,983,322  5,002,700  5,006,278  5,069,820  5,095,076  5,l(i(),457  5,171,478  5,232,631  5,278,213  5,281,363  5,346,649  5,520,852  6/1976  Trevoy  ....................................  430/631  5/1977  Trevoy  ....................................  252/500  1/1991  Elsenbaumer  ...........................  252/500  3/1991  Otagawa  et  al  .........................  252/500  4/1991  Elsenbaumer  ...........................  252/500  12/1991  Jen  et  al  .................................  252/500  3/1992  Oetnent  et al.  ........................  528/422  11/1992  Elsenbaumer  ...........................  252/500  12/1992  Han  .........................................  252/500  8/1993  Cao  et  al.  ...............................  252/500  1/1994  Han et  al  ................................  524/233  1/1994  Shacklette  et  al  ......................  252/500  9/1994  Kama  et  al  .............................  252/500  5/1996  Ikkala  et  al  .............................  252/519  FOREIGN  PATENT  DOCUMENTS  152 632  8/1985  European  Pat.  Off  ..  168 620  1/1986  European  Pat. Off  ..  168 621  446 943  497 514  528178  545729  04-04561  WO  90/01775  WO  90/13601  92-18987  WO  92/22911  93-15510  1/1986  European  Pat.  Off  ..  9/1991  European  Pat.  Off  ..  8/1992  European  Pat.  Off  ..  2/1993  European  Pat. Off  ................  252/500  6/1993  European  Pat. Off  ..  1/1992  Japan  .....................................  252/500  2/1990  WIPO  .  11/1990  WIPO.  10/1992  WIPO  ....................................  252/500  12/1992  WIPO  .  8/1993  WIPO  .......  .............................  252/500  OTHER  PUBLICATIONS  Patent  Abstracts  of  Japan,  vol.  17, No.  124  (C-1035).  Mar.  16. 1993  JP-A-04  304  233,  Tomoegawa  Paper,  Oct.  27,  1992.  Green,  A.G..  and  Woodhead,  A.E.  "Aniline-Black  and  Allied  Compounds.  Part  1".  J. Chem.  Soc  ..  vol.  101.  pp.  1117  (1912).  Koybayashi.  et al.  "Electrochemical  Reactions  ... of  Polya› niline  Film-Coated  Electrodes".  J.  Electroanal.  Chem.  vol.  177,  pp.  281-291  (1984).  Chiang.  J.C.  and  MacDiannid,  A.G .•  "Polyaniline:  Protonic  Acid  Doping  of the  Emeraldine  Form  to the  Metallic  Regime".  Synthetic  Metals,  vol.  13.  pp.  193-205  (1986).  Salaneck.  W.R.  et al.  "A  1\vo-Dimensional-Surface  State  Diagram  for  Polyaniline".  Synthetic  Metals.  vol.  13.  pp.  291-296  (1986).  Plastics  Technology  37  (1991):9,  pp.  19-20.  Primary  Examiner-Michael  Lewis  Assistant  Examiner-Peter  DiMauro  Attorney,  Agent,  or  Firm-Armstrong,  Westerman  Hattori,  McLeland  &  Naughton  Compositions  are  disclosed  comprising  electrically  conduct› ing  polyaniline  and  particular  substituted  aromatic  com› pounds  that  simultaneously  form  hydrogen  bonds  and ring› ring  interactions  with.  respectively,  the  NH-groups  and the  six-membered  rings  of the  conducting  polyanilines.  The  present  conducting  polyaniline  compositions  show  drasti› cally  enhanced  processibility  and their  blends  with  insulat› ing  or  semiconducting  materials  exhibit  significantly  improved  electrical  properties.  [57]  ABSTRACT  21  Claims,  2  Drawing  Sheets  101  100  ()  10-1  0  z  •  0  C  ~  10-2  <  ~  •  -<  1  o- 3  - U)  10-4  ’-- 3  - 10-5  •  10-6  10-7  0  0.05  •  •  I  LJ  0.1  0.15  0.2  PANl(DBSA)$_{0}$ _ 5  weight  fraction 