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# c12) United States Patent Robinson et al. 

# (54) TWO-STEP PHOTORESIST COMPOSITIONS AND METHODS 

(71) Applicants:Alex Philip Graham Robinson, Birmingham (GB); Andreas Frommhold, Am Hermsdorfer Anger (DE); Alan G. Brown, Malvern (GB); Thomas Lada, Somerville, MA (US) 

(72) Inventors: Alex Philip Graham Robinson, Birmingham (GB); Andreas Frommhold, Am Hermsdorfer Anger (DE); Alan G. Brown, Malvern (GB); Thomas Lada, Somerville, MA (US) 

(73) Assignee: IRRESISTIBLE MATERIALS LTD, Swansea, Wiles (GB) 

( *) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by O days. This patent is subject to a terminal dis› claimer. 

(21) Appl. No.: 14/516,472 

(22) Filed: Oct.16, 2014 

## (65) Prior Publication Data 

US 2015/0241773 Al Aug. 27, 2015 

(63) Continuation of application No. 14/187,649, filed on Feb. 24, 2014. 

(51) Int. Cl. 

<img src='content_image/910782.jpg'>

(52) U.S. Cl. CPC .............. G03F 710384 (2013.01); G03F 71038 

## Related U.S. Application Data 

<img src='content_image/910753.jpg'>

# (IO) Patent No.: US 9,383,646 B2 

# (45) Date of Patent: *Jul. 5, 2016 

(58) Field of Classification Search CPC ......... G03F 7/004; G03F 7/027; G03F 7/039; G03F 7/0392; G03F 7/20; G03F 7/32; G03F 7/38; G03F 7/40 See application file for complete search history. 

## (56) References Cited 

<img src='content_image/910781.jpg'>

* cited by examiner 

Primary Examiner - Anca Eoff 

(74) Attorney, Agent, or Firm - The Patent Practice of Szmanda & Shelnut LLC; James G. Shelnut; Charles R. Szmanda 

## (57) ABSTRACT 

The present disclosure relates to novel two-step photoresist compositions and processes. The processes involve removing acid-labile groups in step one and crosslinking the remaining material with themselves or added crosslinking systems in step two. The incorporation of a multistep pathway in the resist catalytic chain increases the chemical gradient in areas receiving a low dose ofirradiation, effectively acting as a built in dose depend quencher-analog and thus enhancing chemi› cal gradient and thus resolution. The photoresist composi› tions and the methods are ideal for fine pattern processing using, for example, ultraviolet radiation, beyond extreme ultraviolet radiation, extreme ultraviolet radiation, X-rays and charged particle rays. Dual functionality photosensitive compositions and methods are also disclosed. 

US009383646B2 

(2013.01); G03F 710382 (2013.01); G03F 712024 (2013.01); G03F 7138 (2013.01) 

## U.S. PATENT DOCUMENTS 

## 14 Claims, 5 Drawing Sheets 

