Organic layer composition, organic layer, and method of forming patterns

Patent metadata

Field	Value
Publication number	US-9908990-B2
Application number	US-201514952269-A
Country	US
Kind code	B2
Filing date	Nov 25, 2015
Priority date	Apr 17, 2015
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

Abstract

An organic layer composition, an organic layer, and a method of forming patterns, the composition including a polymer that includes a substituted or unsubstituted fluorene structure, an additive represented by Chemical Formula 1, and a solvent:

First claim

What is claimed is:

1. An organic layer composition, comprising:
a polymer that includes a substituted or unsubstituted fluorene structure,
an additive represented by Chemical Formula 2-1, Chemical Formula 2-2, Chemical Formula 3-1, or Chemical Formula 3-2, and
a solvent:

wherein, in Chemical Formula 2-1,
X a is CH or nitrogen (N),
R 1a to R 15a are each independently hydrogen, a hydroxy group, or a group represented by one of the following Chemical Formulae A to C, and
at least one of R 1a to R 5a is a group represented by one of Chemical Formulae A to C, at least one of R 6a to R 10a is a group represented by one of Chemical Formulae A to C, and at least one of R 11a to R 15a is a group represented by one of Chemical Formulae A to C,

wherein, in Chemical Formula 2-2,
X a is CH or nitrogen (N), and
R 1 to R 3 are each independently a group represented by one of Chemical Formulae A to C,

wherein, in Chemical Formula 3-1,
X b is a direct bond, —(C q H 2q )—, —(C t R w 2t )—, oxygen (O), sulfur (S), or —S(O 2 )—, q and t being each independently an integer of 1 to 5, and R w being a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 1 to C30 arylalkyl group, a C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, or a combination thereof, and
R 1b to R 10b are each independently hydrogen, a hydroxy group, or a group represented by one of Chemical Formulae A to C,
R 1 —X b —R 2   [Chemical Formula 3-2]

wherein, in Chemical Formula 3-2,
X b is a direct bond, —(C q H 2q )—, —(C t R w 2t )—, oxygen (O), sulfur (S), or —S(O 2 )—, q and t being each independently an integer of 1 to 5, and R w being a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 to C30 arylalkyl group, a C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, or a combination thereof, and
R 1 and R 2 are each independently a group represented by one of Chemical Formulae A to C,
*—(CH 2 ) a —Y 0 —Y 1   [Chemical Formula A]

*—CR x R y R z   [Chemical Formula C]

wherein, in Chemical Formulae A to C,
a and b are each independently an integer of 0 to 10,
c and d are each independently an integer of 1 to 10,
Y 0 is oxygen, sulfur, or —S(O 2 )—,
Y 1 and Y 2 are each independently hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, or a combination thereof,
R x to R z are each independently hydrogen, a hydroxy group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and
* is a linking point.

2. The organic layer composition as claimed in claim 1 , wherein the additive is represented by one of Chemical Formulae 1A to 1G:

wherein, in Chemical Formulae 1A to 1G,
R 33 , R 44 , R 55 , R 66 , R 77 , and R 88 are each independently substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C1 to C20 heteroalkyl group, a substituted or unsubstituted C2 to C30 heterocycloalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C4 alkyl ether group, a substituted or unsubstituted C7 to C20 arylalkylene ether group, a substituted or unsubstituted C1 to C30 haloalkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, or a combination thereof, and
e, f, g, and h are each independently an integer of 1 to 10.

3. The organic layer composition as claimed in claim 1 , wherein the additive represented by Chemical Formula 1 has a molecular weight of about 150 to about 50,000.

4. The organic layer composition as claimed in claim 1 , wherein the additive represented by Chemical Formula 1 is present in the composition in an amount of about 0.1 wt % to about 50 wt %, based on a total weight of the organic layer composition.

5. The organic layer composition as claimed in claim 1 , wherein:
the additive is represented by Chemical Formula 2-1, and
in Chemical Formula 2-1, at least one of R 1a to R 5a is a group represented by Chemical Formula A, at least one of R 6a to R 10a is a group represented by Chemical Formula A, and at least one of R 11a to R 15a is a group represented by Chemical Formula A.

6. The organic layer composition as claimed in claim 5 , wherein, in Chemical Formula A:
a is 1,
Y 0 is oxygen, and
Y 1 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, or a combination thereof.

7. The organic layer composition as claimed in claim 1 , wherein:
the additive is represented by Chemical Formula 3-1, and
in Chemical Formula 3-1, at least one of R 1b to R 5b is a group represented by Chemical Formula A and at least one of R 6b to R 10b is a group represented by Chemical Formula A.

8. The organic layer composition as claimed in claim 7 , wherein, in Chemical Formula A:
a is 0 or 1,
Y 0 is oxygen, and
Y 1 is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 alkenyl group, or a combination thereof.

9. The organic layer composition

Assignees

• Samsung Sdi Co Ltd

Inventors

• Kang Sun Hae
• Nam Youn Hee
• Kim Min Soo
• Rathwell Dominea
• Park You Jung
• Song Hyun Ji
• Yang Sun Young

Classifications

• G03F7/32

  Liquid compositions therefor, e.g. developers · CPC title

• C08G2261/124

  alternating · CPC title

• G03F7/162

  Coating on a rotating support, e.g. using a whirler or a spinner · CPC title

• C08G2261/3424

  non-conjugated, e.g. paracyclophanes or xylenes · CPC title

• G03F7/168

  Finishing the coated layer, e.g. drying, baking, soaking · CPC title