Organic layer composition and method of forming patterns

Patent metadata

Field	Value
Publication number	US-10323159-B2
Application number	US-201615076694-A
Country	US
Kind code	B2
Filing date	Mar 22, 2016
Priority date	Jun 2, 2015
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

An organic layer composition includes a first compound having a thermal shrinkage ratio of about 10% to about 70%, a second compound having a smaller thermal shrinkage ratio than the first compound, and a solvent, and an organic layer obtained by curing the organic layer composition and a method of forming patterns using the organic layer composition are disclosed.
A method of measuring the thermal shrinkage ratio is described in the detailed description.

First claim

What is claimed is:

1. An organic layer composition, consisting essentially of a first compound, a second compound, and a solvent,
the first compound having a thermal shrinkage ratio of about 10% to about 70%, wherein the first compound includes a moiety represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Ar 1 is selected from Group 1:

wherein, in Group 1,
R 10 to R 45 and R 47 to R 57 are independently hydrogen, a hydroxy group, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C20 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
n 10 to n 4 ; and n 47 to n 57 are independently integers of 1 to 6, as further limited by the number of binding sites of the ring to which the respective one of R 10 to R 45 and R 47 to R 57 is attached, and
Y is C═O, oxygen (O), sulfur (S), CR b R c , NR d , or a combination thereof, wherein R b to R d are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, or a combination thereof
R 1 is a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 cycloalkenylene group, a substituted or unsubstituted C7 to C20 arylalkylene group, a substituted or unsubstituted C1 to C20 heteroalkylene group, a substituted or unsubstituted C2 to C30 heterocycloalkylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C2 to C30 alkenylene group, a substituted or unsubstituted C2 to C30 alkynylene group, or a combination thereof,
n 1 is an integer of 1 to 100, and
is a linking point; and
the second compound having a smaller thermal shrinkage ratio than the first compound, wherein the second compound is a compound represented by Chemical Formula 3, a compound represented by Chemical Formula 4, or a combination thereof:

wherein, in Chemical Formula 3,
A is a cyclic group selected from Group 3, or a substituted cyclic group that is the cyclic group selected from Group 3 substituted with another substituent:

R 4 to R 9 are independently a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aromatic ring group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C3 to C20 cycloalkenyl group, or a combination thereof,
X 1 to X 6 are independently hydrogen, a hydroxy group, a thionyl group, a thiol group, a cyano group, a substituted or unsubstituted amino group, a halogen atom, a substituted or unsubstituted C1 to C30 alkoxy group, or a combination thereof,
n 3 to n 8 are independently integers of 0 to 6, and
2≤n 3 +n 4 +n 5 +n 6 +n 7 +n 8 ≤6,

wherein, in Chemical Formula 4,
B is a substituted or unsubstituted cyclic group,
B′ is a substituted or unsubstituted polycyclic aromatic group,
L is a single bond or a substituted or unsubstituted C1 to C6 alkylene group, and
n 9 is an integer ranging from 1 to 4,
wherein the first compound and the second compound are included in a weight ratio of about 50:50 to about 99:1, and
wherein the thermal shrinkage ratio of a compound is calculated by the following method: Method of Measuring a Thermal Shrinkage Ratio as defined in the specification:
[Method of measuring a thermal shrinkage ratio]
about 1 g of a compound is dissolved in about 10 g of propylene glycol monomethyl ether acetate (PGMEA) to prepare a composition,
the composition is coated on a patterned substrate, the coated film thickness (Tk1) is measured at a cell portion and peri portion of the substrate, respectively,
the coated substrate is heat-treated at about 400° C. for about 2 minutes to provide a film, and a thickness (Tk2) of the film is measured at a cell portion and peri portion of the film, respectively, and
each thermal shrinkage ratio (%) at a cell portion and peri portion of the film is obtained by Calculation Equation 1, respectively, and an arithmetic mean value thereof is regarded as a thermal shrinkage ratio of the compound:
Thermal shrinkage ratio of compound=(coating film thickness( Tk 1)−film thickness after curing( Tk 2))/(coating film thickness( Tk 1))*100.  [Calculation Equation 1]

2. The organic layer composition as claimed in claim 1 , wherein the thermal shrinkage ratio of the first compound is about 10% to about 60%.

3. The organic layer composition as claimed in claim 1 , wherein in Chemical Formula 1, R 1 is selected from Group 2:

wherein, in Group 2,
R 58 to R 114 are independently hydrogen, a hydroxy group, a halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C20 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
n 66 is an integer of 0 to 30, and
Z is C═O, oxygen (O), sulfur (S), CR b R c , NR d , or a combination thereof, wherein R b to R d are independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a halogen atom, or a combination thereof.

4. The organic layer composition as claimed in claim 1 , wherein the first compound is a polymer having a weight average molecular weight of about 1,000 to about 30,000.

5. The organic layer composition as claimed in claim 1 , wherein in Chemical Formula 4, B is a cyclic group selected from Group 3, or a substituted cyclic group that is the cyclic group selected from Group 3 substituted with another substituent, and B′ is a pyrene group, a perylene group, a benzoperylene group, a coronene group, or a combination thereof:

6. The organic layer composition as claimed in claim 1 , wherein the first compound and the second compound are included in an amount of about 0.1 wt % to about 50 wt % based on th

Assignees

• Samsung Sdi Co Ltd

Inventors

• Kim Minsoo
• Nam Younhee
• Baek Jaeyeol
• SONG Hyunji
• Yoon Byeri
• Jeong Seulgi
• Hong Seunghee
• Hwang Sunmin

Classifications

• H10P76/405

  characterised by their composition, e.g. multilayer masks · CPC title

• C08G8/10

  with phenol · CPC title

• C09D161/06 Primary

  of aldehydes with phenols · CPC title

• G03F7/0752

  in non photosensitive layers or as additives, e.g. for dry lithography · CPC title

• G03F7/0035

  Multiple processes, e.g. applying a further resist layer on an already in a previously step, processed pattern or textured surface · CPC title