High refractive index cladding material and electro-optical polymer optical waveguide

Patent metadata

Field	Value
Publication number	US-9594189-B2
Application number	US-201214238965-A
Country	US
Kind code	B2
Filing date	Aug 13, 2012
Priority date	Aug 15, 2011
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

There is provided an optical waveguide which has appropriate orientation properties, a production process of which is simple so as to be suitable for producing an electro-optical element, and is able to reduce power consumption of the element due to excellent electro-optical properties, and further can be formed into a thin film and be layered; and a material for the optical waveguide. A cladding material of an optical waveguide, characterized by comprising a polymer compound including a triarylamine structure, and a nonlinear optical compound; and an optical waveguide produced by using the cladding material.

First claim

The invention claimed is:

1. A cladding material of an optical waveguide, comprising:
a polymer compound including a triarylamine structure; and
a nonlinear optical compound, wherein
the polymer compound including the triarylamine structure has a repeating unit of formula (2) or formula (3):

in formula (2) and formula (3), Ar 2 to Ar 4 are each independently any one of divalent organic groups of formula (4) to (8) below; in formula (2), Z 1 is a monovalent organic group of formula (9) below, and Z 2 is a hydrogen atom; and in formula (3), R 15 to R 18 are each independently a hydrogen atom (provided that R 15 and R 18 are not simultaneously hydrogen atoms), or a C 1-5 hydroxyalkyl group,

in the formulas, R 19 to R 52 are each independently a hydrogen atom, a C 1-5 alkyl group, an epoxy group, a carboxy group, a hydroxy group, a C 1-5 alkoxy group, or a halogen atom, in the formula, R 53 to R 57 are each independently a hydrogen atom (provided that R 53 to R 57 are not simultaneously hydrogen atoms), a C 1-5 hydroxyalkyl group, an OR 77 group, a COR 77 group, a COOR 77 group, or an NR 77 R 78 group (in these formulae, R 77 is a C 1-5 hydroxyalkyl group and R 78 is a hydrogen atom).

2. The cladding material according to claim 1 , wherein
the nonlinear optical compound is a compound having a tricyano-bonded furan ring.

3. The cladding material according to claim 2 , wherein
the compound having the tricyano-bonded furan ring is a compound of formula (1):

in the formula, R 1 and R 2 are each independently a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 6-10 aryl group; R 3 to R 6 are each independently a hydrogen atom, a C 1-10 alkyl group, a hydroxy group, a C 1-10 alkoxy group, a C 2-11 alkylcarbonyloxy group, a C 6-10 aryloxy group, a C 7-11 arylcarbonyloxy group, a silyloxy group having a C 1-6 alkyl group and/or a phenyl group, or a halogen atom; R 7 and R 8 are each independently a hydrogen atom, a C 1-5 alkyl group, a C 1-5 haloalkyl group, or a C 6-10 aryl group; and Ar 1 is a divalent organic group of formula (Ar 1 -a) or formula (Ar 1 -b):

in the formula, R 9 to R 14 are each independently a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 6-10 aryl group.

4. The cladding material according to claim 1 , wherein
the repeating unit is represented by formula (13):

in the formula, Z 1 and Z 2 are the same as Z 1 and Z 2 above.

5. An optical waveguide comprising:
a core; and
a cladding that surrounds an entire periphery of the core and has a refractive index smaller than a refractive index of the core, wherein
the cladding is formed of the cladding material as claimed in claim 1 .

6. The optical waveguide according to claim 5 , wherein
the core contains a nonlinear optical compound having a tricyano-bonded furan ring of formula (1) or a derivative of the nonlinear optical compound,

in the formula, R 1 and R 2 are each independently a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 6-10 aryl group; R 3 to R 6 are each independently a hydrogen atom, a C 1-10 alkyl group, a hydroxy group, a C 1-10 alkoxy group, a C 2-11 alkylcarbonyloxy group, a C 6-10 aryloxy group, a C7-11 arylcarbonyloxy group, a silyloxy group having a C 1-6 alkyl group and/or a phenyl group, or a halogen atom; R 7 and R 8 are each independently a hydrogen atom, a C 1-5 alkyl group, a C 1-5 haloalkyl group, or a C 6-10 aryl group; and Ar 1 is a divalent organic group of formula (Ar 1 -a) or formula (Ar 1 -b):

in the formula, R 9 to R 14 are each independently a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 6-10 aryl group.

7. A production method of the optical waveguide as claimed in claim 6 having the core and the cladding that surrounds the periphery of the core and has a refractive index smaller than a refractive index of the core, the production method comprising:
a step of forming a lower cladding using the cladding material comprising:
a polymer compound including a triarylamine structure; and
a nonlinear optical compound

a step of forming on the lower cladding the core containing the nonlinear optical compound having the tricyano-bonded furan ring of formula (1) or the derivative of the nonlinear optical compound; and
a step of forming an upper cladding on the core using the cladding material as in claim 1 , wherein
the production method includes, before and/or after the step of forming of the upper cladding, a step of performing a polarization orientation process on the nonlinear optical compound or the derivative of the nonlinear optical compound contained in the core.

8. A production method of a ridge-type optical waveguide that is a production method of the optical waveguide as claimed in claim 6 having the core and the cladding that surround the periphery of the core and has a refractive index smaller than a refractive index of the core, the production method comprising:
a step of forming a lower cladding using the cladding a step of forming a lower cladding using the cladding material comprising:
a polymer compound including a triarylamine structure; and
a nonlinear optical compound

a step of forming a resist layer having photosensitivity to ultraviolet rays on the lower cladding, radiating ultraviolet light onto a surface of the resist layer through a photomask and carrying out development to form a mask pattern of the core, transferring a core pattern to the lower cladding using the mask pattern as a mask, and removing the resist layer;
a step of forming on the lower cladding the core containing the nonlinear optical compound having the tricyano-bonded furan ring of formula (1) or the derivative of the nonlinear optical compound; and
a step of forming an upper cladding on the core using the cladding material, wherein
the production method includes, before and/or after the step of forming of the upper cladding, a step of performing a polarization orientation process on the nonlinear optical compound or the derivative of the nonlinear optical compound contained in the core.

9. The production method according to claim 7 , in that
the polarization orientation process is an electric field applying process with electrodes.

10. A polymer compound having a repeating unit of formula (2) or formula (3):

in formula (2) and formula (3), Ar 2 to Ar 4 are each independently any one of divalent organic groups of formulae (4) to (8) below; in formula (2), Z 1 is a monovalent organic group of formula (9) below, and Z 2 is a hydrogen atom; and in formula (3), R 15 to R 18 are each independently a hydrogen atom; R 15 to R 18 are not simultaneously hydrogen atoms or a C 1-5 hydroxyalkyl group,

Assignees

• Yokoyama Shiyoshi
• Yamamoto Kazuhiro
• Yasui Kei
• Ozawa Masaaki
• Odoi Keisuke
• Nissan Chemical Ind Ltd
• Univ Kyushu

Inventors

• Yokoyama Shiyoshi
• Yamamoto Kazuhiro
• Yasui Kei
• Ozawa Masaaki
• Odoi Keisuke

Classifications

• G02F1/365

  in an optical waveguide structure (G02F1/377, {G02F1/395} take precedence) · CPC title

• C08G61/12

  Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule · CPC title

• G03F7/0005

  Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor · CPC title

• C08G2261/3162

  Arylamines · CPC title

• C07F7/1804

  Compounds having Si-O-C linkages (Si-O-acyl linkages C07F7/1896) · CPC title