Photoresist comprising nitrogen-containing compound

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Quick Facts

Patent No.: US 9,475,763
App. No.: 14/589,759
Granted: Oct 25, 2016
Kind: B2

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Abstract

New nitrogen-containing compounds are provided that comprise multiple hydroxyl moieties and photoresist compositions that comprise such nitrogen-containing compounds. Preferred nitrogen-containing compounds comprise 1) multiple hydroxyl substituents (i.e. 2 or more) and 2) one or more photoacid-labile groups.

Claims (52)

1. A photoresist composition comprising:

(a) one or more resins;

(b) one or more photoacid generator compounds; and

(c) one or more nitrogen-containing compounds that each comprise 1) two or more hydroxyl substituents and 2) one or more photoacid-labile ester groups and/or photoacid-labile acetal groups, with the exclusion of N-(t-butoxy carbonyl)diethanolamine.

2. The photoresist composition of claim 1 wherein the one or more of the nitrogen-containing compounds comprise a polymer.

3. The photoresist composition of claim 1 wherein the one or more of the nitrogen-containing compounds is non-polymeric.

4. The photoresist composition of claim 1 wherein the one or more nitrogen-containing compounds have a molecular weight of less than 2000.

5. The photoresist composition of claim 1 wherein one or more of the nitrogen-containing compounds is represented by one of the following Formula (I):

wherein R 1 and R 2 are the same or different and at least one of R 1 and R 2 is other than hydrogen, and together R 1 and R 2 comprise at least two hydroxyl groups, or R 1 and R 2 may be taken together to form a ring where the ring (including substituents thereof) comprises at least 2 hydroxy groups; and

X comprises a photoacid-labile group.

6. The photoresist composition of claim 1 wherein one or more of the nitrogen-containing compounds comprise one or more of the following structures:

7. A method for forming a photoresist relief image comprising:

a) applying a coating layer of a photoresist composition of claim 1 on a substrate;

(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

8. The photoresist composition of claim 1 wherein one or more of the nitrogen-containing compounds correspond to the following Formula (IIB):

wherein in Formula (IIB) R 1 and R 2 are the same or different and at least one of R 1 and R 2 is other than hydrogen, and together R 1 and R 2 comprise at least two hydroxyl groups, or R 1 and R 2 may be taken together to form a ring where the ring (including substituents thereof) comprises at least 2 hydroxy groups; and R 1 , R 2 and R 3 each independently represent an optionally substituted straight, branched or cyclic group of 1 to 30 carbon atoms.

9. A photoresist composition comprising:

(a) one or more resins;

(b) one or more photoacid generator compounds; and

wherein R 1 and R 2 are the same or different and at least one of R 1 and R 2 is other than hydrogen, and

wherein R 1 comprises at least two hydroxyl groups, or R 2 comprises at least two hydroxyl groups, or R 1 and R 2 are taken together to form a ring where the ring (including substituents thereof) comprises at least 2 hydroxy groups; and

X comprises a photoacid-labile group.

10. The photoresist composition of claim 9 wherein R 1 comprises at least two hydroxyl groups.

11. The photoresist composition of claim 9 wherein R 2 comprises at least two hydroxyl groups.

12. The photoresist composition of claim 9 wherein R 1 is hydrogen and R 2 is a non-hydrogen group that comprises at least two hydroxyl groups.

13. The photoresist composition of claim 9 wherein R 1 and R 2 are taken together to form a cyclic structure.

14. The photoresist composition of claim 9 wherein one or more of the nitrogen-containing compounds correspond to the following Formula (IIC):

wherein R 1 , R 2 and R 3 each independently represent an optionally substituted straight, branched or cyclic group of 1 to 30 carbon; R 4 represents hydrogen or a straight, branched or cyclic group of 1 to 30 carbon; m1, m2 and m3 are each independently an integer of 0 to 30; n1, n2 and n3 are each independently an integer of 0 or 1; at least two among n1, n2 and n3 are 1.

15. The photoresist composition of claim 9 wherein one or more of the nitrogen-containing compounds correspond to the following Formula (IID):

wherein R 1 , R 2 and R 3 each independently represent a straight, branched or cyclic group of 1 to 30 carbon; R 4 represents hydrogen or an optionally substituted straight, branched or cyclic group of 1 to 30 carbon; n is an integer of 1 to 30; and n is a positive integer e.g. from 1 to 20.

16. A method for forming a photoresist relief image comprising:

a) applying a coating layer of a photoresist composition of claim 9 on a substrate;