CN108473749B - 衍生自降冰片二烯和马来酸酐的聚合物及其用途 - Google Patents
衍生自降冰片二烯和马来酸酐的聚合物及其用途 Download PDFInfo
- Publication number
- CN108473749B CN108473749B CN201680076530.1A CN201680076530A CN108473749B CN 108473749 B CN108473749 B CN 108473749B CN 201680076530 A CN201680076530 A CN 201680076530A CN 108473749 B CN108473749 B CN 108473749B
- Authority
- CN
- China
- Prior art keywords
- alkyl
- polymer
- group
- general formula
- maleic anhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/02—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F232/06—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/08—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having two condensed rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/04—Anhydrides, e.g. cyclic anhydrides
- C08F22/06—Maleic anhydride
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/02—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings
- C08F32/06—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having no condensed rings having two or more carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L45/00—Compositions of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L47/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Compositions of derivatives of such polymers
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/322—Aqueous alkaline compositions
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562273553P | 2015-12-31 | 2015-12-31 | |
| US62/273,553 | 2015-12-31 | ||
| PCT/US2016/069375 WO2017117483A1 (en) | 2015-12-31 | 2016-12-30 | Polymers derived from norbornadiene and maleic anhydride and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108473749A CN108473749A (zh) | 2018-08-31 |
| CN108473749B true CN108473749B (zh) | 2019-11-26 |
Family
ID=57985011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201680076530.1A Active CN108473749B (zh) | 2015-12-31 | 2016-12-30 | 衍生自降冰片二烯和马来酸酐的聚合物及其用途 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9834627B2 (https=) |
| JP (1) | JP6726281B2 (https=) |
| KR (1) | KR101930045B1 (https=) |
| CN (1) | CN108473749B (https=) |
| TW (1) | TWI692674B (https=) |
| WO (1) | WO2017117483A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI692674B (zh) * | 2015-12-31 | 2020-05-01 | 日商住友電木股份有限公司 | 衍生自降莰二烯和馬來酸酐之聚合物及其用途 |
| EP3837266A1 (en) | 2018-08-17 | 2021-06-23 | Massachusetts Institute of Technology | Degradable polymers of a cyclic silyl ether and uses thereof |
| JP7322372B2 (ja) * | 2018-09-28 | 2023-08-08 | 住友ベークライト株式会社 | ポリマー、樹脂組成物、及び、樹脂膜 |
| CN114450318A (zh) * | 2019-09-26 | 2022-05-06 | 住友电木株式会社 | 聚合物、感光性树脂组合物、树脂膜和电子装置 |
| EP4058501A1 (en) | 2019-11-15 | 2022-09-21 | Massachusetts Institute of Technology | Functional oligomers and functional polymers including hydroxylated polymers and conjugates thereof and uses thereof |
| DE102020130523B4 (de) | 2019-12-31 | 2023-08-10 | Taiwan Semiconductor Manufacturing Co., Ltd. | Verfahren zur bildung einer fotolackstruktur |
| US12547075B2 (en) * | 2019-12-31 | 2026-02-10 | Taiwan Semiconductor Manufacturing Company, Ltd. | Method of forming photoresist pattern |
| CN117062852A (zh) | 2021-02-01 | 2023-11-14 | 麻省理工学院 | 可再加工的组合物 |
| US20240270898A1 (en) * | 2021-06-01 | 2024-08-15 | Massachusetts Institute Of Technology | Latent-fluoride containing polymers for triggered degradation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103649220A (zh) * | 2011-07-14 | 2014-03-19 | 住友电木株式会社 | 在成像式曝光于光化辐射下之后形成构图层的聚合物及其组合物 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02146045A (ja) * | 1988-02-17 | 1990-06-05 | Tosoh Corp | フォトレジスト組成物 |
| KR900700923A (ko) | 1988-02-17 | 1990-08-17 | 야마구찌 도시아끼 | 포토레지스트 조성물 |
| JP2638887B2 (ja) * | 1988-02-26 | 1997-08-06 | 東ソー株式会社 | 感光性組成物 |
| JP2961722B2 (ja) | 1991-12-11 | 1999-10-12 | ジェイエスアール株式会社 | 感放射線性樹脂組成物 |
| KR960009295B1 (ko) * | 1991-09-12 | 1996-07-18 | 미쓰이세끼유 가가꾸고오교오 가부시끼가이샤 | 환상올레핀 수지 조성물 |
| JPH0570639A (ja) * | 1991-09-12 | 1993-03-23 | Mitsui Petrochem Ind Ltd | 環状オレフイン樹脂組成物 |
| US6013413A (en) * | 1997-02-28 | 2000-01-11 | Cornell Research Foundation, Inc. | Alicyclic nortricyclene polymers and co-polymers |
| KR100254472B1 (ko) * | 1997-11-01 | 2000-05-01 | 김영환 | 신규한 말레이미드계 또는 지방족 환형 올레핀계 단량체와 이들 단량체들의 공중합체수지 및 이수지를 이용한 포토레지스트 |
| JP3262108B2 (ja) | 1998-09-09 | 2002-03-04 | 東レ株式会社 | ポジ型感光性樹脂組成物 |
| JP2002201226A (ja) | 2000-12-28 | 2002-07-19 | Jsr Corp | 共重合体およびそれを用いた感放射線性樹脂組成物 |
| JP3952756B2 (ja) | 2001-11-29 | 2007-08-01 | 日本ゼオン株式会社 | 感放射線性樹脂組成物及びその利用 |
| US7799883B2 (en) | 2005-02-22 | 2010-09-21 | Promerus Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| JP4684139B2 (ja) * | 2005-10-17 | 2011-05-18 | 信越化学工業株式会社 | レジスト保護膜材料及びパターン形成方法 |
| JP4666166B2 (ja) * | 2005-11-28 | 2011-04-06 | 信越化学工業株式会社 | レジスト下層膜材料及びパターン形成方法 |
| US7745104B2 (en) * | 2006-08-10 | 2010-06-29 | Shin-Etsu Chemical Co., Ltd. | Bottom resist layer composition and patterning process using the same |
| US8541523B2 (en) | 2010-04-05 | 2013-09-24 | Promerus, Llc | Norbornene-type polymers, compositions thereof and lithographic process using such compositions |
| JP5579553B2 (ja) | 2010-09-17 | 2014-08-27 | 信越化学工業株式会社 | レジスト下層膜材料、レジスト下層膜形成方法、パターン形成方法 |
| KR101572049B1 (ko) | 2012-09-25 | 2015-11-26 | 프로메러스, 엘엘씨 | 사이클로올레핀성 중합체를 함유하는 말레이미드 및 그의 용도 |
| WO2015038412A2 (en) | 2013-09-16 | 2015-03-19 | Promerus, Llc | Amine treated maleic anhydride polymers with pendent silyl group, compositions and applications thereof |
| WO2015038411A2 (en) * | 2013-09-16 | 2015-03-19 | Promerus, Llc | Amine treated maleic anhydride polymers, compositions and applications thereof |
| CN106068288B (zh) * | 2014-03-06 | 2018-05-01 | 住友电木株式会社 | 聚合物、光敏性树脂组合物和电子装置 |
| TWI692674B (zh) * | 2015-12-31 | 2020-05-01 | 日商住友電木股份有限公司 | 衍生自降莰二烯和馬來酸酐之聚合物及其用途 |
-
2016
- 2016-12-29 TW TW105143893A patent/TWI692674B/zh not_active IP Right Cessation
- 2016-12-30 JP JP2018533664A patent/JP6726281B2/ja active Active
- 2016-12-30 KR KR1020187018753A patent/KR101930045B1/ko active Active
- 2016-12-30 US US15/394,970 patent/US9834627B2/en active Active
- 2016-12-30 WO PCT/US2016/069375 patent/WO2017117483A1/en not_active Ceased
- 2016-12-30 CN CN201680076530.1A patent/CN108473749B/zh active Active
-
2017
- 2017-10-12 US US15/782,103 patent/US9944730B2/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103649220A (zh) * | 2011-07-14 | 2014-03-19 | 住友电木株式会社 | 在成像式曝光于光化辐射下之后形成构图层的聚合物及其组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US9944730B2 (en) | 2018-04-17 |
| US20170190810A1 (en) | 2017-07-06 |
| JP6726281B2 (ja) | 2020-07-22 |
| US20180044449A1 (en) | 2018-02-15 |
| US9834627B2 (en) | 2017-12-05 |
| JP2019503415A (ja) | 2019-02-07 |
| TWI692674B (zh) | 2020-05-01 |
| KR20180082607A (ko) | 2018-07-18 |
| KR101930045B1 (ko) | 2018-12-17 |
| CN108473749A (zh) | 2018-08-31 |
| WO2017117483A1 (en) | 2017-07-06 |
| TW201740189A (zh) | 2017-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108473749B (zh) | 衍生自降冰片二烯和马来酸酐的聚合物及其用途 | |
| JP5860193B2 (ja) | マレイミド含有シクロオレフィンポリマーおよびその利用 | |
| TWI411876B (zh) | 光敏介電樹脂組成物、由其形成之薄膜、及包括此薄膜之半導體及顯示裝置 | |
| CN109313388B (zh) | 负型感光性组合物 | |
| JP6564065B2 (ja) | 永久的な誘電体としてのマレイミド及びシクロオレフィンモノマーのポリマー | |
| TWI672323B (zh) | 無氟可光圖案化之含酚官能基之聚合物組成物 | |
| US11048168B2 (en) | Permanent dielectric compositions containing photoacid generator and base | |
| TWI684826B (zh) | 可光成像組成物、硬化產物形成方法、硬化產物及包含該硬化產物的光電子或微電子裝置 | |
| JP6959351B2 (ja) | 下層膜形成用樹脂材料、レジスト下層膜、レジスト下層膜の製造方法および積層体 | |
| US20250250378A1 (en) | Cyanonorbornene polymers for oil resistant photoimageable compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20191022 Address after: Tokyo, Japan Applicant after: Sumitomo Dianwood Co., Ltd. Address before: Ohio, USA Applicant before: Promirus Co., Ltd. |
|
| TA01 | Transfer of patent application right | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |