# US 11,029,497 B2 · Curable composition, cured product thereof, optical member and optical device

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- Number: US 11,029,497 B2
- Document ID: US11029497B2
- Status: Granted
- Kind: B2
- Application number: 16/001,223
- Filed: 2018-06-06
- Published: 2018-10-04
- Granted: 2021-06-08
- Earliest claimed: 2012-08-31
- Assignees: Daicel Corporation
- Applicants: Daicel Corporation
- Inventors: Takashi Kubo; Hiroki Takenaka
- Web page: https://patentgrep.com/patent/US11029497B2

## CPC

- G02B 13/0085: {employing wafer level optics}
- B29D 11/00365: {Production of microlenses (lenticular sheets B29D11/00278)}
- C08G 59/02: Polycondensates containing more than one epoxy group per molecule
- C08G 59/226: {Mixtures of di-epoxy compounds}
- C08G 59/24: carbocyclic
- C08G 59/306: {containing silicon}
- C08G 59/3218: {Carbocyclic compounds}
- C08G 59/3281: {containing silicon}
- G02B 1/041: {Lenses}
- B29C 39/02: for making articles of definite length, i.e. discrete articles
- B29K 2063/00: Use of {EP, i.e.} epoxy resins {or derivatives thereof}, as moulding material
- B29K 2083/00: Use of polymers having silicon, with or without sulfur, nitrogen, oxygen, or carbon only, in the main chain, as moulding material
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS

## Abstract

An object of the present invention is to provide a curable composition that can be cured satisfactorily and can form a cured product having a high glass transition temperature as maintained and having high mechanical strength. A curable composition includes a siloxane (A), a cycloaliphatic epoxide (B), and a curing agent (C). The siloxane (A) contains at least two epoxy groups per molecule. The cycloaliphatic epoxide (B) in the curable composition is preferably a compound represented by Formula (I): wherein X is selected from a single bond and a linkage group.

## Claims

### Claim 1

A curable composition comprising:
a cycloaliphatic epoxide (A);
a siloxane (B) comprising at least two epoxy groups per molecule;
a curing agent (C);
an oxetane compound; and
a hydrogenated glycidyl ether epoxide;
wherein the siloxane (B) is one or more compounds represented by the following formulae:

### Claim 2 (depends on 1)

The curable composition according to claim 1,
wherein the cycloaliphatic epoxide (A) comprises a compound represented by Formula (I):
wherein X is selected from a single bond and a linkage group.

### Claim 3 (depends on 1)

The curable composition according to claim 1,
wherein the siloxane (B) comprising at least two epoxy groups per molecule comprises a cycloaliphatic epoxy group as at least one of the epoxy groups.

### Claim 4 (depends on 1)

The curable composition according to claim 1,
wherein the curable composition comprises the cycloaliphatic epoxide (A) in a content of from 5 to 60 percent by weight based on the total amount (100 percent by weight) of the curable composition.

### Claim 5 (depends on 1)

The curable composition according to claim 1,
wherein the cycloaliphatic epoxide (A) comprises 3,4,3′,4′-diepoxybicyclohexyl.

### Claim 6 (depends on 1)

A cured product of the curable composition according to claim 1.

### Claim 7 (depends on 6)

An optical element comprising
a cured product of the curable composition according to claim 6.

### Claim 8 (depends on 7)

An optical device comprising
the optical element according to claim 7.

### Claim 9

A method for producing a wafer-level lens, the method comprising subjecting a curable composition to one of cast molding and injection molding,
wherein the curable composition comprises:
a cycloaliphatic epoxide (A);
a siloxane (B) comprising at least two epoxy groups per molecule;
a curing agent (C);
an oxetane compound; and
a hydrogenated glycidyl ether epoxide;
wherein the siloxane (B) is one or more compounds represented by the following formulae:

### Claim 10 (depends on 9)

The method for producing a wafer-level lens, according to claim 9, wherein a cast molding or an injection molding comprises the steps of:
1a or 1b) preparing a wafer-level-lens mold comprising at least one lens pattern;
2a or 2b) bringing or injecting the curable composition for a wafer-level lens into contact with the wafer-level-lens mold; and
3a or 3b) applying at least one of heat and light to the curable composition for a wafer-level lens to cure the curable composition to thereby give a cured product of the curable composition.

### Claim 11 (depends on 10)

The method for producing a wafer-level lens, according to claim 10,
wherein the cast molding or the injection molding further comprises, after the step 3a or 3b), the step of
4a or 4b) annealing the cured product of the curable composition for a wafer-level lens.

### Claim 12 (depends on 10)

The method for producing a wafer-level lens, according to claim 10,
wherein the cast molding further comprises, after the step 3a), the step of
5a) cutting the cured product of the curable composition for a wafer-level lens.

### Claim 13 (depends on 9)

A wafer-level-lens sheet obtained by the method for producing a wafer-level lens according to claim 9.

### Claim 14 (depends on 9)

A wafer-level lens obtained by the method for producing a wafer-level lens according to claim 9.

### Claim 15 (depends on 14)

An optical device comprising
the wafer-level lens according to claim 14.

### Claim 16 (depends on 1)

A wafer-level lens stack comprising
a plurality of wafer-level lenses,
the plurality of wafer-level lenses constituting the stack comprising
a wafer-level lens obtained by curing and molding the curable composition for a wafer-level lens according to claim 1.

### Claim 17 (depends on 1, 16)

A method for producing a wafer-level lens stack, the method comprising the steps of:
1c) preparing a wafer-level-lens mold comprising at least one lens pattern;
2c) bringing the curable composition according to claim 1 into contact with the wafer-level-lens mold;
3c) applying at least one of heat and light to the curable composition for a wafer-level lens to cure the curable composition to thereby give a wafer-level-lens sheet;
4c) stacking a plurality of wafer-level-lens sheets comprising the wafer-level-lens sheet to give a wafer-level-lens sheet stack; and
5c) cutting the wafer-level-lens sheet stack to give the wafer-level lens stack according to claim 16.

### Claim 18 (depends on 17)

The method for producing a wafer-level lens stack, according to claim 17, the method further comprising, between the step 3c) and the step 4c), the step of
6c) annealing the wafer-level-lens sheet.

### Claim 19 (depends on 9)

The method for producing a wafer-level lens, according to claim 9,
wherein the cycloaliphatic epoxide (A) comprises a compound represented by Formula (I):
wherein X is selected from a single bond and a linkage group.

### Claim 20 (depends on 1)

The curable composition according to claim 1,
wherein the content of the hydrogenated glycidyl ether epoxide is 5 to 40 percent by weight based on the total amount (100 percent by weight) of curable compounds contained in the curable composition.
