# US 11,111,225 B2 · Calixarene compound and curable composition

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,111,225 B2
- Document ID: US11111225B2
- Status: Granted
- Kind: B2
- Application number: 16/463,037
- Filed: 2017-11-16
- Published: 2019-09-12
- Granted: 2021-09-07
- Earliest claimed: 2016-12-01
- Assignees: DIC Corporation
- Applicants: DIC Corporation
- Inventors: Shinya Yamamoto; Masanori Miyamoto; Tomoyuki Imada
- Web page: https://patentgrep.com/patent/US11111225B2

## CPC

- C07D 303/23: Oxiranylmethyl ethers of compounds having one hydroxy group bound to a six-membered aromatic ring, the oxiranylmethyl radical not being further substituted, i.e. [IMAGE cpc-sch-C07D-1030.gif]
- B29C 33/60: Releasing, lubricating or separating agents {(in general C10M)}
- C07C 43/225: containing halogen
- C07C 43/23: containing hydroxy or O-metal groups
- C07C 49/83: polycyclic
- C07C 59/66: the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C 69/653: Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
- C07C 69/712: the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
- C07C 323/12: the carbon skeleton being acyclic and saturated
- C07C 323/16: the carbon skeleton containing six-membered aromatic rings
- C07C 327/06: to hydrogen atoms or to carbon atoms of an acyclic saturated carbon skeleton
- C07D 201/00: Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D 209/48: with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07D 303/34: with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
- C07D 305/06: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
- C07F 1/00: Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F 7/04: Esters of silicic acids
- C07F 9/09: Esters of phosphoric acids
- C07F 9/12: with hydroxyaryl compounds
- C07F 9/38: Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids {; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]}
- C07F 9/4006: {Esters of acyclic acids which can have further substituents on alkyl}
- C08K 5/00: Use of organic ingredients
- C08L 33/10: Homopolymers or copolymers of methacrylic acid esters
- G03F 7/0002: {Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping}
- H10P 76/00: Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography
- C07C 2603/92: with a condensed ring system consisting of at least two mutually uncondensed aromatic ring systems, linked by an annular structure formed by carbon chains on non-adjacent positions of the aromatic system, e.g. cyclophanes
- H10P 76/2041: {Photolithographic processes}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

A compound useful as a release agent, and a release agent, a curable composition, and a nanoimprint lithography resin material each containing the compound are provided. More specifically, a calixarene compound with a molecular structure represented by the following structural formula (1) and a composition containing the calixarene compound are provided. wherein R1 denotes a structural moiety with a perfluoroalkyl group, R2 denotes a hydrogen atom, a polar group, a polymerizable group, or a structural moiety with a polar group or a polymerizable group, R3 denotes a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aryl group that may have a substituent, n denotes an integer in the range of 2 to 10, and * denotes a bonding point with an aromatic ring.

## Claims

### Claim 1

A release agent that is a calixarene compound with a molecular structure represented by the following structural formula (1-1) or (1-2):
wherein, in structural formula (1-1) and (1-2):
R1 denotes a structural moiety represented by structural formula (2):
—R4—Y—R4—RF (2)
wherein, in structural formula (2):
R4 independently denotes a direct bond or an alkylene group having 1 to 6 carbon atoms,
RF denotes a perfluoroalkyl group, and
Y denotes a carbonyl group, an oxygen atom, or a sulfur atom;
R2 denotes a structural moiety represented by:
wherein, in structural formula (3-1), (3-2), (3-4), (3-7), (4-1), (4-2), (4-3), (4-4), (4- 5), (4-6), or (4-7):
R4 independently denotes an alkylene group having 1 to 6 carbon atoms,
R5 independently denotes an alkyl group having 1 to 3 carbon atoms,
and R6 denotes a hydrogen atom or a methyl group;
R3 denotes a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aryl group that may have a substituent; and
n denotes an integer in the range of 4 to 10.

### Claim 2 (depends on 1)

The release agent that is the calixarene compound according to claim 1, wherein R2 denotes a structural moiety with a vinyl group, a vinyloxy group, an ethynyl group, an ethynyloxy group, a (meth)acryloyl group, or a (meth)acryloyloxy group.

### Claim 3 (depends on 1)

A curable composition comprising: the release agent that is the calixarene compound according to claim 1; and a curable resin material.

### Claim 4 (depends on 1)

A nanoimprint lithography resin material comprising the release agent that is the calixarene compound according to claim 1.

### Claim 5 (depends on 2)

A curable composition comprising: the release agent that is the calixarene compound according to claim 2; and a curable resin material.

### Claim 6 (depends on 2)

A nanoimprint lithography resin material comprising the release agent that is the calixarene compound according to claim 2.