Composition for optical material and optical material using the same

Patent metadata

Field	Value
Publication number	US-10508173-B2
Application number	US-201615566838-A
Country	US
Kind code	B2
Filing date	Jun 10, 2016
Priority date	Jun 17, 2015
Publication date	Dec 17, 2019
Grant date	Dec 17, 2019

Abstract

The present invention provides a composition for an optical material containing a ring compound (a) represented by formula (1), an episulfide compound (b), and sulfur (c), wherein the content of the ring compound (a) in the composition for an optical material is in the range of 5-70 mass %, the content of the episulfide compound (b) is in the range of 20-90 mass %, and the content of the sulfur (c) is in the range of 1-39 mass %. (In the formula, X represents S, Se or Te. a to f=0 to 3, 8≥(a+c+e)≥1, 8≥(b+d+f)≥2, and (b+d+f)≥(a+c+e).) This composition for an optical material has a high refractive index as an optical characteristic, and has sufficient heat resistance and good mold release characteristics.

First claim

The invention claimed is:

1. A composition for optical materials containing
a ring compound (a) that is at least one substance selected from the group consisting of dithiirane, 1,2-dithietane, 1,3-dithietane, trithietane, 1,2,3-trithiolane, 1,2,4-trithiolane, tetrathiolane, 1,2,3-trithiane, 1,2,4-trithiane, 1,2,3,4-tetrathiane, 1,2,4,5-tetrathiane, 1,2,3,4-tetrathiepane, 1,2,3,5-tetrathiepane, 1,2,4,5-tetrathiepane, 1,2,4,6-tetrathiepane, 1,2,3,4,5-pentathiepane, 1,2,3,4,6-pentathiepane, 1,2,3,5,6-pentathiepane, hexathiepane, diselecyclobutane, triselecyclobutane, triselecyclopentane, tetraselecyclopentane, diselecyclohexane, tetraselecyclohexane, pentaselecyclohexane, tetraselecycloheptane, pentaselecycloheptane, hexaselecycloheptane, ditellurocyclobutane, tritellurocyclobutane, tritellurocyclopentane, tetratellurocyclopentane, tetratellurocyclohexane, pentatellurocyclohexane, tetratellurocycloheptane, pentatellurocycloheptane, and hexatellurocycloheptane,
an episulfide compound (b),
sulfur (c), and
a thiol compound (d) that is at least one substance selected from the group consisting of methanedithiol, 1,2-ethanedithiol, (sulfanylmethyldisulfanyl)methanethiol, bis(2-mercaptoethyl) sulfide, 2,5-bis(mercaptomethyl)-1,4-dithiane, 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,2,6,7-tetramercapto-4-thiaheptane, tetramercaptopentaerythritol, 1,3-bis(mercaptomethyl)benzene, and thiiranemethanethiol,
wherein in the composition for optical materials, the content of the ring compound (a) is 5 to 70% by mass, the content of the episulfide compound (b) is 20 to 90% by mass, the content of the sulfur (c) is 1 to 39% by mass, and the thiol compound (d) is 0.1 to 15 parts by mass relative to 100 parts by mass of the total amount of the ring compound (a), the episulfide compound (b), and the sulfur (c).

2. The composition for optical materials according to claim 1 , wherein in the composition for optical materials, the total content of the ring compound (a) and the episulfide compound (b) is 60 to 99% by mass.

3. The composition for optical materials according to claim 1 , wherein the mass ratio between the ring compound (a) and the episulfide compound (b) ((a)/(b)) is 10/90 to 70/30.

4. The composition for optical materials according to claim 1 , wherein the ring compound (a) is at least one substance selected from the group consisting of 1,2-dithietane, trithietane, 1,2,3-trithiolane, 1,2,4-trithiolane, tetrathiolane, 1,2,3-trithiane, 1,2,4-trithiane, 1,2,3,4-tetrathiane, 1,2,4,5-tetrathiane, pentathiane, 1,2,3,4-tetrathiepane, 1,2,3,5-tetrathiepane, 1,2,4,5-tetrathiepane, 1,2,4,6-tetrathiepane, 1,2,3,4,5-pentathiepane, 1,2,3,4,6-pentathiepane, 1,2,3,5,6-pentathiepane, and hexathiepane.

5. The composition for optical materials according to claim 1 , wherein the episulfide compound (b) is represented by formula (2) below:

wherein: m represents an integer of 0 to 4; and n represents an integer of 0 to 2.

6. A polymerizable and curable composition, which contains: the composition for optical materials according to claim 1 ; and a polymerization catalyst in an amount of 0.0001 to 10% by mass relative to the total amount of the composition for optical materials.

7. A resin obtained by curing the composition for optical materials according to claim 1 .

8. An optical material obtained by using the resin according to claim 7 .

9. The optical material according to claim 8 , which further has a hard coat layer having a refractive index of 1.67 or higher.

10. The optical material according to claim 9 , which further has an antireflection film.

11. A resin obtained by curing the polymerizable and curable composition according to claim 6 .

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• IMAGAWA Yousuke
• HORITA Akinobu
• Yamamoto Yoshiaki
• Horikoshi Hiroshi

Classifications

• C08G79/00

  Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon {with or without the latter elements in the main chain of the macromolecule} · CPC title

• C08G75/06 Primary

  from cyclic thioethers · CPC title

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• G02B1/11

  Anti-reflection coatings · CPC title

• C07D341/00

  Heterocyclic compounds containing rings having three or more sulfur atoms as the only ring hetero atoms · CPC title