US 2025/0085632 A1Published application

Uv nanoimprinted lithographic devices made from polycycloolefinic polymers for microfluidics

AssigneePromerus, LLC

InventorLARRY F. RHODES

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Abstract

Embodiments in accordance of this invention relates generally to a composition containing polymers formed from one or more polycycloolefinic monomers at least one of which monomers containing a pendant maleimide group and a monomer which is capable of undergoing 2+2 cycloaddition reaction with the pendant group. More specifically, in an embodiment of this invention there is provided a polymer derived from one or more substituted or unsubstituted norbornene derivatives among which at least one monomer contains a substituted or unsubstituted maleimide pendant group, which polymer in combination with a monomer containing a substituted or unsubstituted maleimide forms a composition which can be used for a number of photopatternable polymeric layer when exposed to suitable actinic radiation. For example, the compositions of this invention can be used to form UV initiated nanoimprinted layers having utility in a number of applications including microfluidic devices, among others.

Claims20

Dependent claims

A composition comprising:

a) a polycycloolefinic polymer comprising at least one first repeat unit of formula (IA),
said first repeat unit is derived from a monomer of formula (I):
wherein:
denotes a place of bonding with another repeat unit;
m is 0, 1 or 2;
at least one of R1, R2, R3 and R4 is selected from the group consisting of:
a radical of formula (IIA):
a radical of formula (IIB):
a radical of formula (IIC):
and
a radical of formula (IID):
wherein:
n is an integer from 0 to 10, inclusive;
and
R9 and R10 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C3-C6)alkyl;
or
R9 taken together with R10 and the carbon atoms to which they are attached to form a substituted or unsubstituted (C3-C14)cyclic, (C5-C14)bicyclic or (C5-C14)tricyclic ring optionally containing one or more double bonds;
the remaining R1, R2, R3 and R4 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3-C16)alkyl, (C3-C10)cycloalkyl, (C6-C12)bicycloalkyl, (C6-C12)aryl and (C6-C12)aryl(C1-C6)alkyl;
or
one of R1 and R2 taken together with one of R3 and R4 and the carbon atoms to which they are attached to form a substituted or unsubstituted (C3-C14)cyclic, (C5-C14)bicyclic or (C5-C14)tricyclic ring optionally containing one or more double bonds;
and
b) a compound of formula (III):
Y—(B)q (III)
wherein,
q is an integer from 1 to 6;
B is a radical of formula (IV):
wherein R9 and R10 are as defined above;
Y is selected from the group consisting of substituted or unsubstituted methyl, ethyl, (C3-C16)alkyl, substituted or unsubstituted (C3-C16)cycloalkyl, substituted or unsubstituted (C3-C16)cycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C6-C16)bicycloalkyl, substituted or unsubstituted (C6-C16)bicycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C5-C16)tricycloalkyl, substituted or unsubstituted (C5-C16)tricycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C6-C10)aryl, substituted or unsubstituted (C6-C10)aryl(C1-C16)alkyl, substituted or unsubstituted (C5-C10)heteroaryl and substituted or unsubstituted (C6-C10)heteroaryl(C1-C16)alkyl, wherein the substituents are selected from the group consisting of halogen, methoxy, ethoxy, (C3-C16)alkoxy and tris-(C1-C16)alkoxysilyl.

25 more elements

A kit for forming a plurality of patterned film layers comprising:

a) a polycycloolefinic polymer comprising at least one first repeat unit of formula (IA),
said first repeat unit is derived from a monomer of formula (I):
wherein:
denotes a place of bonding with another repeat unit;
m is 0, 1 or 2;
at least one of R1, R2, R3 and R4 is selected from the group consisting of:
a radical of formula (IIA):
a radical of formula (IIB):
and
a radical of formula (IIC):
wherein:
n is an integer from 0 to 10, inclusive;
and
R9 and R10 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C3-C6)alkyl;
or
R9 taken together with R10 and the carbon atoms to which they are attached to form a substituted or unsubstituted (C3-C14)cyclic, (C5-C14)bicyclic or (C5-C14)tricyclic ring optionally containing one or more double bonds;
the remaining R1, R2, R3 and R4 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3-C16)alkyl, (C3-C10)cycloalkyl, (C6-C12)bicycloalkyl, (C6-C12)aryl and (C6-C12)aryl(C1-C6)alkyl;
or
one of R1 and R2 taken together with one of R3 and R4 and the carbon atoms to which they are attached to form a substituted or unsubstituted (C3-C14)cyclic, (C5-C14)bicyclic or (C5-C14)tricyclic ring optionally containing one or more double bonds;
and
b) a compound of formula (III):
Y—(B)q (III)
wherein,
q is an integer from 1 to 6;
B is a radical of formula (IV):
wherein R9 and R10 are as defined above;
Y is selected from the group consisting of substituted or unsubstituted methyl, ethyl, (C3-C16)alkyl, substituted or unsubstituted (C3-C16)cycloalkyl, substituted or unsubstituted (C3-C16)cycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C6-C16)bicycloalkyl, substituted or unsubstituted (C6-C16)bicycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C5-C16)tricycloalkyl, substituted or unsubstituted (C5-C16)tricycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C6-C10)aryl, substituted or unsubstituted (C6-C10)aryl(C1-C16)alkyl, substituted or unsubstituted (C5-C10)heteroaryl and substituted or unsubstituted (C6-C10)heteroaryl(C1-C16)alkyl, wherein the substituents are selected from the group consisting of halogen, methoxy, ethoxy, (C3-C16)alkoxy and tris-(C1-C16)alkoxysilyl.

24 more elements

A method of forming a patterned layers comprising:

a) coating a substrate with a composition, said composition comprising:
i) a polycycloolefinic polymer comprising at least one first repeat unit of formula (IA), said first repeat unit is derived from a monomer of formula (I):
wherein:
denotes a place of bonding with another repeat unit;
m is 0, 1 or 2;
at least one of R1, R2, R3 and R4 is selected from the group consisting of:
a radical of formula (IIA):
a radical of formula (IIB):
and
a radical of formula (IIC):
wherein:
n is an integer from 0 to 10, inclusive;
and
R9 and R10 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C3-C6)alkyl;
or
R9 taken together with R10 and the carbon atoms to which they are attached to form a substituted or unsubstituted (C3-C14)cyclic, (C5-C14)bicyclic or (C5-C14)tricyclic ring optionally containing one or more double bonds;
the remaining R1, R2, R3 and R4 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3-C16)alkyl, (C3-C10)cycloalkyl, (C6-C12)bicycloalkyl, (C6-C12)aryl and (C6-C12)aryl(C1-C6)alkyl;
or
one of R1 and R2 taken together with one of R3 and R4 and the carbon atoms to which they are attached to form a substituted or unsubstituted (C3-C14)cyclic, (C5-C14)bicyclic or (C5-C14)tricyclic ring optionally containing one or more double bonds;
and
ii) a compound of formula (III):
Y—(B)q (III)
wherein,
q is an integer from 1 to 6;
B is a radical of formula (IV):
wherein R9 and R10 are as defined above;
Y is selected from the group consisting of substituted or unsubstituted methyl, ethyl, (C3-C16)alkyl, substituted or unsubstituted (C3-C16)cycloalkyl, substituted or unsubstituted (C3-C16)cycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C6-C16)bicycloalkyl, substituted or unsubstituted (C6-C16)bicycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C5-C16)tricycloalkyl, substituted or unsubstituted (C5-C16)tricycloalkyl(C1-C6)alkyl, substituted or unsubstituted (C6-C10)aryl, substituted or unsubstituted (C6-C10)aryl(C1-C16)alkyl, substituted or unsubstituted (C5-C10)heteroaryl and substituted or unsubstituted (C6-C10)heteroaryl(C1-C16)alkyl, wherein the substituents are selected from the group consisting of halogen, methoxy, ethoxy, (C3-C16)alkoxy and tris-(C1-C16)alkoxysilyl;
b) placing a patterned soft stamp on the coated substrate;
c) placing a glass slide on top of the soft stamp to form a stack;
d) exposing the stack to a suitable actinic radiation;
e) removing the glass slide and the stamp to obtain the patterned substrate.

28 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/830,880Filed 11 Sep 2024
Priority: 11 Sep 2023
Published: 13 Mar 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

G03F 7/039
Photosensitive materials: macromolecular compounds which are photodegradable, e.g. positive electron resists
G03F 7/16
Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g.…
G03F 7/2002
Exposure; Apparatus therefor: with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film…
G03F
Photomechanical production of textured or patterned surfaces

Family

Application63/537,737Us provisional application · filed 11 Sep 2023
US 2025/0085632 A1This patent

From the US filing history. Foreign family members aren’t listed.

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