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# c12) United States Patent 

# Prokopowicz et al. 

# (54) COATING COMPOSITIONS 

(71) Applicant: Rohm and Haas Electronic Materials LLC, Marlborough, MA (US) 

(72) Inventors: Gregory P. Prokopowicz, Worcester, MA (US); Michael K. Gallagher, Hopkinton, MA (US) 

(73) Assignee: Rohm and Haas Electronic Materials LLC, Marlborough, MA (US) 

( *) 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.: 14/543,460 

(22) Filed: Nov. 17, 2014 

## (65) Prior Publication Data 

US 2015/0072290 Al Mar. 12, 2015 

## Related U.S. Application Data 

(62) Division of application No. 11/417,374, filed on May 4, 2006, now Pat. No. 8,889,344. 

(60) Provisional application No. 60/682,941, filed on May 19, 2005, provisional application No. 60/678,032, filed on May 4, 2005. 

(51) Int. Cl. 

<img src='content_image/946169.jpg'>

(52) U.S. Cl. CPC ................ G03F 71091 (2013.01); C0SK 3/36 (2013.01); C09D 129104 (2013.01); C09D 133102 (2013.01); G03F 7111 (2013.01); G03F 712041 (2013.01) 

(58) Field of Classification Search CPC . G03F 7/09; G03F 7/091; G03F 7/092; G03F 7/20; G03F 7/2041; C08K 3/36 USPC ................................ 430/271.1, 272.1, 273.1 See application file for complete search history. 

<img src='content_image/946171.jpg'>

# (IO) Patent No.: US 10,474,032 B2 

# (45) Date of Patent: *Nov. 12, 2019 

## (56) References Cited 

<img src='content_image/946164.jpg'>

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/946165.jpg'>

Zirconium Dioxide (1314-23-4), Chemical Book, 2008.* 

Final Office Action issued in counterpart Korean Application No. 10-2016-0054286 (4 pages). 

English language summary of Office Action and Search Report issued in Taiwan counterpart apoplication 106-2(60()091190- 10620224230, 2017 (4 pages). 

English language summary of Office Action dated Apr. 13, 2017 issued in Japanese counterpoart Application No. 2016-088986 (3 pages). 

* cited by examiner 

Primary Examiner - Anca Eoff (74) Attorney, Agent, or Firm - Mintz Levin Cohn Ferris Glovsky and Popeo, P.C.; Peter F. Corless 

## (57) ABSTRACT 

In one aspect, coating compositions are provided that com› prise a component a component that comprises one or more silicon, antimony, aluminum, yttrium, cerium, lanthanum, tin, titanium, zirconium, hafnium, indium or zinc com› pounds. In another aspect, coating compositions are pro› vided that comprise a plurality of discrete particles. Pre› ferred coating compositions of the invention are useful for antireflective purposes, particularly with an underlaying photoresist coating layer, as well as for a barrier layer in immersion lithography. 

US010474032B2 

## U.S. PATENT DOCUMENTS 

## OTHER PUBLICATIONS 

## 19 Claims, 2 Drawing Sheets 

