Composition for high refractive index low dispersion resins for composite diffractive optical elements, and composite diffractive optical element using the same

Patent metadata

Field	Value
Publication number	US-11214650-B2
Application number	US-201716091314-A
Country	US
Kind code	B2
Filing date	Apr 6, 2017
Priority date	Apr 11, 2016
Publication date	Jan 4, 2022
Grant date	Jan 4, 2022

Abstract

A composition for a high refractive index, low dispersion resin for a close-contact double layer-type composite diffractive optical element that is highly photocurable and provides a high productivity, and a close-contact double layer-type composite diffractive optical element using such composition are provided. A composition for a high refractive index, low dispersion resin for a close-contact double layer-type composite diffractive optical element includes a thiol compound represented by general formula (1) or an oligomer synthesized by use of a thiol compound represented by general formula (1) (A component); and an ene compound including two or more polymerizable unsaturated bonds (B component). (In the formula, p represents an integer of 2 to 5; X p and Z p independently represent a hydrogen atom or a mercaptomethyl group; a ratio of sulfur atoms in a molecule is 40 to 80% by mass; and the number of thiol groups is 3 or larger.).

First claim

The invention claimed is:

1. A composition for a high refractive index and low dispersion resin for a close-contact double layer-type composite diffractive optical element, the composition comprising:
a thiol compound represented by formula (1) or an oligomer synthesized by use of a thiol compound represented by formula (1) (A component); and
an ene compound including two or more polymerizable unsaturated bonds (B component):

where p represents an integer of 2 to 5; X p and Z p independently represent a hydrogen atom, a mercapto group, or a mercaptomethyl group; a ratio of sulfur atoms in a molecule is 40 to 80% by mass; and the number of thiol groups is 3 or larger.

2. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the thiol compound represented by formula (1) is at least one selected from the group consisting of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane (4-mercaptomethyl-3,6-dithia-1,8-octanedithiol), 4,8-bis(mercaptomethyl)-1,11-dimercapto-3,6,9-trithiaundecane (4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane), 4,7-bis(mercaptomethyl)-1,11-dimercapto-3,6,9-trithiaundecane (4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane), and 5,7-bis(mercaptomethyl)-1,11-dimercapto-3,6,9-trithiaundecane (5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane).

3. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the component A is an oligomer synthesized by use of the thiol compound represented by formula (1).

4. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the component B is a non-aromatic ene compound.

5. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the composition includes the component A at a ratio of 30% by mass or higher.

6. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the composition has a viscosity at 23° C. in the range of 500 to 20000 mPa·s.

7. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the component A contains an oligomer in which a part of a thiol group in the thiol compound represented by formula (1) is bonded with an isocyanate compound.

8. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the composition has an Abbe number in the range of 30 to 50.

9. A high refractive index and low dispersion resin obtained by curing the composition for a high refractive index and low dispersion resin according to claim 1 .

10. A close-contact double layer-type composite diffractive optical element, comprising:
the high refractive index and low dispersion resin according to claim 9 ; and
a low refractive index and high dispersion resin having a refractive index lower than that of, and exhibiting a dispersibility higher than that of, the high refractive index and low dispersion resin.

11. The close-contact double layer-type composite diffractive optical element according to claim 10 , wherein the high refractive index and low dispersion resin and the low refractive index and high dispersion resin have a refractive index difference at an e line of 0.02 to 0.1; have a refractive index difference at an F line that is 0.8 to 0.98 times the refractive index difference at the e line; and have a refractive index difference at a C line that is 1.02 to 1.26 times the refractive index difference at the e line.

12. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the component B comprises triallyl isocyanurate, triallyl cyanurate, tetraallyloxyethane, hydrogenated triallyl trimellitate, oligoethyleneglycoldi(meth)acrylate, dimethyloltricyclodecanedi(meth)acrylate, trimethylolpropanetri(meth)acrylate, pentaerythritoltetra(meth)acrylate, dipentaerythritolhexa(meth)acrylate, or 2,2′-thiodiethanethioldi(meth)acrylate.

13. The composition for a high refractive index and low dispersion resin according to claim 1 , wherein the ratio of the B component in the composition for the high refractive index and low dispersion resin is 20 to 70% by mass.

Assignees

• Mitsubishi Gas Chemical Co

Inventors

• NAMIKI Kousuke
• Koshiishi Eiji
• Furukawa Kikuo
• Horikoshi Hiroshi

Classifications

• C08L81/02

  Polythioethers; Polythioether-ethers · CPC title

• C08G75/06

  from cyclic thioethers · CPC title

• C08G75/04

  from mercapto compounds or metallic derivatives thereof (C08G75/0204 takes precedence) · CPC title

• C08G18/757

  containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title