IP Library Granted Patent US 12,492,313
Granted Patent B2
US 12,492,313 · App. 18/349,834 · Granted Dec 9, 2025

Materials for forming a nucleation-inhibiting coating and devices incorporating same

Inventors: Michael Helander (Mississauga, CA); Scott Nicholas Genin (Mississauga, CA); Zhibin Wang (Mississauga, CA)
Assignee: OTI Lumionics Inc.
C09D5/24C09D7/63H10K59/80522H10K71/621H10K85/111
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Quick Facts
Patent No.
US 12,492,313
App. No.
18/349,834
Granted
Dec 9, 2025
Kind
B2
Abstract

An opto-electronic device comprising a nucleation inhibiting coating (NIC) disposed on a surface of the device in a first portion of a lateral aspect thereof; and a conductive coating disposed on a surface of the device in a second portion of the lateral aspect thereof; wherein an initial sticking probability of the conductive coating is substantially less for the NIC than for the surface in the first portion, such that the first portion is substantially devoid of the conductive coating; and wherein the NIC comprises a compound having a formula such as that illustrated by the following formula:

Claims (46)

1 . An opto-electronic device comprising:

a nucleating inhibiting coating (NIC) disposed on a surface of the device in a first portion of a lateral aspect thereof; and

a conductive coating comprising a conductive coating material and disposed on a surface of the device in a second portion of the lateral aspect thereof;

wherein:

the first portion is substantially devoid of a closed coating of the conductive material,

the NIC comprises a compound comprising a core moiety that is an anthracene moiety, and at least one moiety bonded thereto, and

at least one of the at least one moiety comprises a fluoroaryl group.

2 . The opto-electronic device of claim 1 , wherein the fluoroaryl group is a trifluoroaryl group.

3 . The opto-electronic device of claim 1 , wherein at least one of the at least one moiety comprises at least one additional substituent selected from at least one of: a fluorine atom, a fluoroalkyl group, a fluoroaryl group, a trifluoroaryl group, and a fluoroalkoxy group.

4 . The opto-electronic device of claim 1 , wherein the compound has a formula selected from a group consisting of Formulae (I), (II), (III), (IV), (V), (VI), (VII), and (VIII):

wherein:

Ar 1 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms; or a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms;

R a represents one or more substituent groups, which are independently: H, D (deutero), F, Cl, alkyl including C 1 -C 6 alkyl, cycloalkyl, silyl, fluoroalkyl, arylalkyl, aryl, heteroaryl, alkoxy, haloalkoxy, fluoroalkoxy, fluoroaryl, and trifluoraryl;

R b represents one or more substituent groups, which are independently: H, D (deuteron), F, Cl, alkyl including C 1 -C 6 alkyl, cycloalkyl, silyl, fluoroalkyl, arylalkyl, aryl, haloaryl, heteroaryl, alkoxy, haloalkoxy, fluoroalkoxy, fluoroaryl, and trifluoroaryl;

Ar 2 represents a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroarylene group having 4 to 50 carbon atoms;

Ar 3 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms; or a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms;

Ar 4 represents a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroarylene group having 4 to 50 carbon atoms;

Ar 5 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 4 to 50 carbon atoms; or a substituted or unsubstituted heteroarylene group having 5 to 60 carbon atoms;

Ar 6 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; a substituted or unsubstituted haloaryl group having 6 to 50 carbon atoms; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms; and

Ar 7 represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; a substituted or unsubstituted haloaryl group having 6 to 50 carbon atoms; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 5 to 60 carbon atoms.

5 . The opto-electronic device of claim 4 , wherein Ar 1 is selected from the group consisting of 1-naphthyl; 2-naphthyl; 1-phenanthryl; 2-phenanthryl; 10-phenanthryl; 9-phenanthryl; 1-anthracenyl; 2-anthracenyl; 3-anthracenyl; 9-anthracenyl; benzanthracenyl; pyrenyl; pyridine; quinoline; isoquinoline; pyrazine; quinoxaline; arcidine; pyrimidine; quinazoline; pyridazine; cinnoline and phthalzine.

6 . The opto-electronic device of claim 4 , wherein R a is selected from the group consisting of H, D, F, Cl, methyl, methoxy, ethyl, t-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, fluoralkoxy, difluoromethoxy, trifluoromethoxy, fluoroethyl, polyfluoroethyl, fluorophenyl, trifluorophenyl, and trifluoromethoxyphenyl.

7 . The opto-electronic device of claim 4 , wherein R b is selected from the group consisting of H, D, F, Cl, methyl, methoxy, ethyl, t-butyl, fluoromethyl, difluoromethyl, trfluoromethyl, fluoroalkoxy, diflouromethoxy, trifluoromethoxy, fluoroethyl, polyfluoroethyl, fluorophenyl, trifluorophenyl, and trifluoromethoxyphenyl.

8 . The opto-electronic device of claim 4 , wherein Ar 2 is selected from the group consisting of phenylene; naphthylene; anthracylene; phenanthrylene; benzanthracylene; and pyrenylene.

9 . The opto-electronic device of claim 4 , wherein Ar 3 is selected from the group consisting of 1-naphthyl; 2-naphthyl; 1-phenanthryl; 2-phenanthryl; 10-phenanthryl; 9-phenanthryl; 1-anthracenyl; 2-anthracenyl; 3-anthracenyl; 9-anthracenyl; benzanthracenyl; pyrenyl; pyridine; quinoline; isoquinoline; pyrazine; quinoxaline; arcidine; pyrimidine; quinazoline; pyridazine; cinnoline; and phthalazine.

10 . The opto-electronic device of claim 4 , wherein Ar 4 is selected from the group consisting of phenylene; naphthylene; anthracylene; phenanthrylene; benzanthracylene; pyrenylene; and benzimidazole.

11 . The opto-electronic device of claim 4 , wherein Ar 5 is selected from the group consisting of phenyl; 1-naphthyl; 2-naphthyl; 1-phenanthryl; 2-phenanthryl; 10-phenanthryl; 9-phenanthryl; 1-anthracenyl; 2-anthracenyl; 3-anthracenyl; 9-anthracenyl; benzanthracenyl; and pyrenyl.

12 . The opto-electronic device of claim 4 , wherein Ar 6 is selected from the group consisting of phenyl, 1-naphthyl; 2-naphthyl; 1-phenanthryl; 2-phenanthryl; 10-phenanthryl; 9-phenanthryl; 1-anthracenyl; 2-anthracenyl; 3-anthracenyl; 9-anthracenyl; benzanthracenyl; pyrenyl; 4-fluorophenyl; 3,4,5-trifluorophenyl; and 4-(trifluoromethoxy)phenyl.

13 . The opto-electronic device of claim 4 , wherein Ar 7 is selected from the group consisting of phenyl, 1-naphthyl; 2-naphthyl; 1-phenanthryl; 2-phenanthryl; 10-phenanthryl; 9-phenanthryl; 1-anthracenyl; 2-anthracenyl; 3-anthracenyl; 9-anthracenyl; benzanthracenyl; pyrenyl; 4-fluorophenyl; 3,4,5-trifluorophenyl; and 4-(trifluoromethoxy)phenyl.

14 . The opto-electronic device of claim 1 , further comprising at least one emissive region, wherein the device comprises a first electrode, a second electrode and a semiconducting layer between the first electrode and the second electrode in the at least one emissive region.

15 . The opto-electronic device of claim 14 , wherein the first portion comprises the at least one emissive region, and the second electrode extends between the NIC and the semiconducting layer in the first portion.

16 . The opto-electronic device of claim 15 , wherein the second portion comprises at least a part of a non-emissive region.

17 . The opto-electronic device of claim 15 , wherein a thickness of the NIC in the at least one emissive region of the first portion is modulated to adjust an optical microcavity effect thereof.

18 . The opto-electronic device of claim 15 , wherein the conductive coating is electrically coupled to the second electrode.

19 . The opto-electronic device of claim 15 , wherein the conductive coating coats at least a part of the second electrode in the second portion.

20 . The opto-electronic device of claim 15 , comprising at least one intermediate coating between the second electrode and the conductive coating along at least a part thereof.

21 . The opto-electronic device of claim 20 , wherein the intermediate coating comprises a nucleation promoting coating (NPC).

22 . The opto-electronic device of claim 15 , wherein the second portion comprises at least one additional emissive region.

23 . The opto-electronic device of claim 22 , wherein at least one of the at least one additional emissive region of the second portion of the device comprises a first electrode, a second electrode and a semiconducting layer between the first electrode and the second electrode, wherein the second electrode comprises the conductive coating.

24 . The opto-electronic device of claim 23 , wherein a wavelength of light emitted from the at least one additional emissive region of the second portion of the device differs from a wavelength of light emitted from the at least one emissive region of the first portion of the device.

25 . The opto-electronic device of claim 14 , wherein the second portion comprises the at least one emissive region, and the second electrode extends between the conductive coating and the semiconducting layer in the second portion.

26 . The opto-electronic device of claim 25 , wherein the first portion comprises at least a part of a non-emissive region.

27 . The opto-electronic device of claim 26 , wherein the first portion is substantially light-transmissive therethrough.

28 . The opto-electronic device of claim 27 , wherein the second electrode extends in the first portion and the NIC is disposed on a surface of the second electrode.

29 . The opto-electronic device of claim 1 , wherein the conductive coating comprises an auxiliary electrode.

30 . The opto-electronic device of claim 1 , wherein the core moiety further comprises at least one of: a fluorine atom, a fluoroalkyl group, a fluoroaryl group, a trifluoroaryl group, and a fluoroalkoxy group.

Continuity (5)
Continuation 17436562
Provisional Application 62830338 · Apr 5, 2019
Provisional Application 62822715 · Mar 22, 2019
Provisional Application 62815267 · Mar 7, 2019
Related Publication 20240074230A1 · Feb 29, 2024
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