Optical device including birefringent polymer

• US 4,446,305 A
• Filed: 03/02/1981
• Issued: 05/01/1984
• Est. Priority Date: 03/02/1981
• Status: Expired due to Term

• Current Assignee: Polaroid Corporation (PLR IP Holdings LLC)
• Original Assignee: Polaroid Corporation (PLR IP Holdings LLC)
• Inventors: Sahatjian, Ronald A., Gaudiana, Russell, Rogers, Howard G., Bilofsky, Ruth C.
• Primary Examiner(s): ANDERSON, HAROLD
• Application Number:
  US06/238,054
• Time in Patent Office: 1,156 Days
• Field of Search: 528/348, 528/345, 528/208, 528/331, 528/363
• US Class Current: 528/348
• CPC Class Codes: G02B 1/08 made of polarising materials
• CPC Class Codes: G02B 5/305 including organic materials, e.g. polymeric layers
• CPC Class Codes: Y10T 428/24942 including components having same physical characteristic in differing degree

Abstract

Optical devices including a molecularly oriented highly birefringent polymer are disclosed. The devices include molecularly oriented polymers comprising recurring units which exhibit a distribution of high electron density about the long axes of the polymer and the recurring units thereof. Transparent birefringent polymers comprising a plurality of recurring units having a substantially cylindrical distribution of electron density about the long axis of such units and the chain-extended polymers are included in optical devices and articles. The polymers exhibit high birefringence and simulate in a polymer the optical properties of a uniaxial crystal.

Claims

1. An optical device comprising a transparent molecularly oriented highly birefringent polymer, said highly birefringent polymer comprising repeating molecular units exhibiting high electron density substantially cylindrically distributed about the long axes of the polymer and the repeating units thereof, said highly birefringent polymer being substantially optically uniaxial exhibiting only two indices of refraction.

2. The device of claim 1 wherein the birefringence of said polymer is in relation to the molecular configuration of said repeating molecular units and the cylindrical or ellipsoidal electron density distribution about said axes according to a dimensionless geometric index G represented by the relationship

3. The device of claim 2 wherein said geometric index G has a value of one or higher.

4. The device of claim 3 wherein said geometric index G has a value of 1.2 or higher.

5. The device of claim 1 wherein said molecularly oriented highly birefringent polymer has a birefringence of at least 0.2.

6. The device of claim 5 wherein said molecularly oriented highly birefringent polymer has a birefringence of at least about 0.4.

7. The device of claim 2 wherein said molecularly oriented highly birefringent polymer has a birefringence of at least about 0.2.

8. The device of claim 7 wherein said molecularly oriented highly birefringent polymer has a birefringence of at least 0.4.

9. The device of claim 1 wherein said molecularly oriented highly birefringent polymer is in the form of a unidirectionally stretched polymer layer.

10. The device of claim 1 wherein said molecularly oriented highly birefringent polymer comprises:

recurring units of the formula ##STR69## wherein R and R¹ are each hydrogen, alkyl, aryl, alkaryl or aralkyl, and each of A and B is a divalent radical, at least one of said A and B radicals being a divalent radical selected from the group consisting of;

##STR70## where U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and r is an integer from 1 to 4, said U, Wp and Xr substitution being sufficient to provide said radical with a non-coplanar molecular configuration; and

##STR71## where each of Y and Z is hydrogen or a substituent other than hydrogen and each t is an integer from 1 to 4, with the provisio that when each said Z is hydrogen, at least one said Y substituent is a substituent other than hydrogen positioned on the corresponding nucleus ortho with respect to the ##STR72## moiety of said radical, said Z and Yt substitution being sufficient to provide said radical with a non-coplanar molecular configuration.

11. The device of claim 10 wherein each of said A and B radicals of said recurring units of formula I is a divalent radical having the formula ##STR73## wherein U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and r is an integer from 1 to 4, said U, Wp and Xr substitution being sufficient to provide said radical with a non-coplanar molecular configuration.

12. The device of claim 11 wherein each said A and B radical is a divalent radical having the formula ##STR74## wherein each of U and X is a substituent other than hydrogen.

13. The device of claim 12 wherein each of said U and X substituents is selected from the group consisting of halogen, nitro, alkoxy and substituted-alkyl.

14. The device of claim 13 wherein each said U and X substituent is bromo.

15. The device of claim 13 wherein each of said U and X substituent is nitro.

16. The device of claim 13 wherein each said U and X substituent is trifluoromethyl.

17. The device of claim 16 wherein said divalent radical A is a radical having the formula ##STR75## wherein p is the integer 3, r is the integer 4 and each of U, W and X is a substituent other than hydrogen.

18. The device of claim 17 wherein each said U, W and X substituent is halogen.

19. The device of claim 18 wherein each said U, W and X substituent is fluoro.

20. The device of claim 11 wherein said divalent radical A is a radical having the formula ##STR76## wherein p is the integer 3 r is the integer 4 and each of U, W and X is a substituent other than hydrogen;

and said divalent radical B is a radical having the formula ##STR77## wherein each of U and X is a substituent other than hydrogen.

21. The device of claim 20 wherein, in said radical A having the formula ##STR78## where p is the integer 3 and r is the integer 4, each of said U, W and X substituents is fluoro, and wherein, in said radical B having the formula ##STR79## each said U and X substituent is bromo.

22. The device of claim 10 wherein, in the recurring units of formula I, said divalent radical A is the radical having the formula ##STR80## said divalent radical B is a radical having the formula ##STR81## wherein U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and r is an integer from 1 to 4, said U, Wp and Xr substitution being sufficient to provide said radical with a non-coplanar molecular configuration.

23. The device of claim 22 wherein said divalent radical B is a radical having the formula ##STR82## wherein each of U and X is a substituent selected from the group consisting of halogen, nitrogen, nitro, alkoxy and substituted-alkyl.

24. The device of claim 23 wherein each of said U and X is halogen.

25. The device of claim 23 wherein each of said U and X is bromo.

26. The device of claim 23 wherein each of said U and X is trifluoromethyl.

27. The device of claim 10 wherein, in the recurring units of formula I, said divalent radical A is a radical having the formula ##STR83## wherein each of U and X is a substituent other than hydrogen, and said divalent radial B is a radical having the formula ##STR84## wherein U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and r is an integer from 1 to 4, said U, Wp and Xr substitution being sufficient to provide said radical with a non-coplanar molecular configuration.

28. The device of claim 27 wherein, in said radical A, each of said U and X substituents is halogen;

and wherein, in said radical B, p is the integer one, r is the integer two and each X substituent is selected from the group consisting of halogen, alkoxy and substituted-alkyl.

29. The device of claim 28 wherein said radical B is a radical having the formula ##STR85## where W and X are each alkoxy.

30. The device of claim 10 wherein, in the recurring units of formula I, said divalent radical is the radical having thje formula ##STR86## and said divalent radical B is a radical having the formula ##STR87## wherein U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and r is an integer from 1 to 4, said U, Wp and Xr substitution being sufficient to provide said radical with a non-coplanar molecular configuration.

31. The device of claim 30 wherein said divalent radical B is a radical having the formula ##STR88## wherein each of U and X is a substituent selected from the group consisting of halogen, nitro, alkoxy and substituted-alkyl.

32. The device of claim 31 wherein each of said U and X is halogen.

33. The device of claim 32 wherein each of said U and X is bromo.

34. The device of claim 31 wherein each of said U and X is trifluoromethyl.

35. The device of claim 10 wherein, in the recurring units of formula I, said divalent radical A is the radical having the formula ##STR89## and said divalent radical B is a radical having the formula ##STR90## wherein U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and r is an integer from 1 to 4, said U, Wp and Xr substitution being sufficient to provide said radical with a non-coplanar molecular configuration.

36. The device of claim 35 wherein said divalent radical B is a radical having the formula ##STR91## wherein each of U and X is a substituent selected from the group consisting of halogen, nitro, alkoxy and substituted-alkyl.

37. The device of claim 36 wherein each of said U and X is halogen.

38. The device of claim 37 wherein each of said U and X is bromo.

39. The device of claim 36 wherein each of said U and X is trifluoromethyl.

40. The device of claim 10 wherein, in the recurring units of formula I, each of said A and B radicals is a divalent having the formula ##STR92## where each of Y and Z is hydrogen or a substituent other than hydrogen and each t is n integer from 1 to 4, with the proviso that when each said Z is hydrogen, at least one Y substituent is a substituent other than hydrogen positioned on the corresponding nucleus ortho with respect to the ##STR93## moiety of said radical, said Z and Yt substitution being sufficient to provide said radical with a non-coplanar moelcular configuration.

41. The device of claim 40 wherein, in each of said radicals A and B, each said Z is hydrogen, each said t is the integer one and each corresponding Y substituent is a substituent other than hydrogen position on the corresponding nucleus ortho with respect to the ##STR94## moiety of the radical.

42. The device of claim 41 wherein each said Y substituent is selected from the group consisting of halogen, nitro and alkoxy.

43. The device of claim 40 wherein, in each of said radicals A and B, each Y is hydrogen, each t is the integer four, one said Z is hydrogen and the remaining and Z substituent is halogen.

44. The device of claim 43 wherein said halogen is bromo.

45. The device of claim 10 wherein, in the recurring units of formula I, said divalent radical A is a radical having the formula ##STR95## where each of Y and Z is hydrogen or a substituent other than hydrogen and each t is an integer from 1 to 4, with the proviso that when each said Z is hydrogen, at least one said Y substituent is a substituent other than hydrogen positioned on the corresponding nucleus ortho with respect to the ##STR96## moiety of said radical, said Z and Yt substitution being sufficient to provide said radical with a non-planar molecular configuration;

and said divalent radical B is a radical having the formula ##STR97## wherein U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and r is an integer from 1 to 4, said U, Wp and Xr substitution being sufficient to provide said radical with a non-coplanar configuration.

46. The device of claim 45 wherein, in said radical A, each said t is the integer four, each corresponding Y is hydrogen, one said Z is hydrogen and the remaining said Z is halogen.

47. The device of claim 46 wherein said halogen is bromo.

48. The device of claim 46 wherein said radical B is a radical having the formula ##STR98## wherein each of U and X is a substituent selected from the group consisting of halogen, nitro, alkoxy and substituted-alkyl.

49. The device of claim 48 wherein each of U and X is halogen.

50. The device of claim 49 wherein each halogen is bromo.

51. The device of claim 10 wherein, in said recurring units of formula I, radical A is the radical having the formula ##STR99## said divalent radical B is a substituted-quaterphenylene radical having the formula ##STR100## wherein each U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, each P is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and each r is an integer from 1 to 4, said U, W_p and X_r substitution being sufficient to provide said radical with a non-coplanar molecular configuration.

52. the device of claim 51 wherein said divalent radical B is a substituted-quaterphenylene radical having the formula ##STR101## wherein each of U and X is a substituent selected from the group consisting of halogen, nitro, alkoxy and trifluoromethyl.

53. The device of claim 52 wherein each of said U and X substituents is trifluoromethyl.

54. The device of claim 10 wherein, in said recurring units of formula I, said divalent radical A is the radical having the formula ##STR102## and said divalent radical B is a substituted-quaterphenylene radical having the formula ##STR103## wherein each U is a substituent other than hydrogen, each W is hydrogen or a substituent other than hydrogen, each p is an integer from 1 to 3, each X is hydrogen or a substituent other than hydrogen and each r is an integer from 1 to 4, said U, Wp and Xr substitution being sufficient to provide said radical with a non-coplanar molecular configuration.

55. The device of claim 54 wherein said divalent radical B is a substituted-quaterphenylene radical having the formula ##STR104## wherein each of U and X is a substituent selected from the group consisting of halogen, nitro, alkoxy and trifluoromethyl.

56. The device of claim 55 wherein each of said U and X substituents is trifluoromethyl.