IP Library Granted Patent US 10,095,113
Granted Patent B2
US 10,095,113 · App. 14/334,612 · Granted Oct 9, 2018

Photoresist and method

Inventors: Wei-Han Lai (New Taipei, TW); Ching-Yu Chang (Yuansun Village, TW)
Assignee: Taiwan Semiconductor Manufacturing Company
G03F7/0397G03F7/2041G03F7/322G03F7/325
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Quick Facts
Patent No.
US 10,095,113
App. No.
14/334,612
Filed
Jul 17, 2014
Granted
Oct 9, 2018
Kind
B2
Examiner
LEE, SIN J
Art Unit
1722
USPC
430/270.1
Abstract

Shrinkage and mass losses are reduced in photoresist exposure and post exposure baking by utilizing a small group which will decompose. Alternatively a bulky group which will not decompose or a combination of the small group which will decompose along with the bulky group which will not decompose can be utilized. Additionally, polar functional groups may be utilized in order to reduce the diffusion of reactants through the photoresist.

Claims (38)

1. A photoresist comprising a polymer, wherein the polymer comprises:

a first group which will decompose by action of acids, bases, or free radicals generated by a photoactive compound, the first group which will decompose having a first number of carbon atoms;

a second group which will decompose by the action of the acids, the bases, or the free radicals generated by the photoactive compound, the second group which will decompose having a second number of carbon atoms smaller than the first number of carbon atoms and smaller than nine carbon atoms, wherein the photoresist is a negative tone photoresist and wherein the first group which will decompose has a loading of greater than about 30%, wherein the first group which will decompose and the second group which will decompose are part of a single polymer, and wherein the second group which will decompose comprises a cycloalkyl group and further comprises a C4-C5 alkyl group, an acetyl group, or an acetyl alkyl group; and

a first bulky group which will not decompose by the action of the acids, the bases, or the free radicals generated by the photoactive compound, wherein the second group which will decompose is bonded to the first bulky group which will not decompose.

2. The photoresist of claim 1 , wherein the first bulky group which will not decompose comprises between nine carbon atoms and thirty carbon atoms.

3. The photoresist of claim 1 , wherein the second number of carbon atoms is greater than four carbon atoms.

4. The photoresist of claim 1 , wherein the repeating units comprising the second group which will decompose are present in the amount of greater than 5% of all the repeating units present within the polymer.

5. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

6. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

7. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

8. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

wherein Rd is a C0-C1 alkyl group.

9. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

10. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

wherein Rd is a C0-C2 alkyl group.

11. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

wherein Rd is a C0-C2 alkyl group.

12. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

wherein Rd is a C0-C1 alkyl group.

13. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

wherein Rd is a C0-C1 alkyl group.

14. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

15. The photoresist of claim 1 , wherein the second group which will decompose has the following structure:

wherein Rd is a C0-C3 alkyl group.

16. A photoresist comprising:

a solvent;

a photoactive compound; and

a polymer resin, wherein the photoresist is a negative tone photoresist and wherein the polymer resin comprises:

a first group which will cleavage by action of acids, bases, or free radicals generated by a photoactive compound, wherein the first group which will cleavage has greater than 9 carbon atoms, wherein the first group which will cleavage has a loading of greater than about 45%; and

a second group which will cleavage by action of the acids, the bases, or the free radicals generated by the photoactive compound, wherein the second group which will cleavage has no more than nine carbon atoms, and wherein the second group which will cleavage comprises both a cycloalkyl group and an acetyl group or an acetyl alkyl group.

17. The photoresist of claim 16 , wherein the repeating units comprising the second group which will cleavage are present in the amount of greater than 5% of all the repeating units present within the polymer resin.

18. The photoresist of claim 16 , wherein the polymer resin further comprises a first bulky group which will not cleavage, wherein the first bulky group which will not cleavage comprises at least 9 carbon atoms and less than or equal to 30 carbon atoms.

19. The photoresist of claim 18 , wherein the polymer resin further comprises a polar functional group bonded to the first bulky group which will not cleavage.

20. A photoresist comprising a polymer, wherein the polymer comprises:

a hydrocarbon backbone;

a bulky group which will decompose by action of acids, bases, or free radicals generated by a photoactive compound, wherein the bulky group which will decompose is bonded to the hydrocarbon backbone, wherein the bulky group which will decompose has greater than nine carbon atoms and has a loading of greater than about 45%;

a small group which will decompose by action of the acids, the bases, or the free radicals generated by the photoactive compound, wherein the small group which will decompose is bonded to the hydrocarbon backbone, wherein the small group which will decompose has less than nine carbon atoms and has a loading of greater than about 5%, and wherein the small group which will decompose comprises a cycloalkyl group and a C4-C5 alkyl group; and

a lactone group bonded to the hydrocarbon backbone, wherein the photoresist is a negative tone photoresist.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 3, 2018
From: LAI, WEI-HAN; CHANG, CHING-YU; WU, CHEN-HAU
To: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY, LTD.
Reel/Frame 047057/0371 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2014
From: LAI, WEI-HAN; CHANG, CHING-YU
To: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY
Reel/Frame 033338/0448 →
Continuity (2)
Provisional Application 61912967 · Dec 6, 2013
Related Publication 20150160552A1 · Jun 11, 2015