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US 2012/0232237 A1Published application
Fluorinated Monomers, Oligomers and Polymers for Use in Organic Electronic Devices
AssigneeNational Research Council of Canada
InventorsZhao Li, Jianfu Ding, Jianping Lu, Ye Tao
Life of this patent
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Abstract
Compounds of Formula (I): (formula (I)) where: X1 and X2 are the same or different and each is independently Cl, Br, I, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; and, Y is O, S, Se, NR1, R1C—CR2 or R1C═CR2, wherein R1 and R2 are the same or different and are each independently H or an organic group, are useful as monomers to produce oligomers or polymers that are useful in organic electronic devices.
Claims21
1:
- A compound of Formula (I):
- where:
- X1 and X2 are the same or different and each is independently Cl, Br, I, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group;
- and, Y is O, S, Se, NR1, R1C—CR2 or R1C═CR2, wherein R1 and R2 are the same or different and are each independently H or an organic group.
1 more element
2:
- The compound according to claim 1, wherein the aryl groups are C6-C18-aryl groups and the heteroaryl groups are C3-C14-heteroaryl groups having one or more of N, O or S in the ring.
3:
- The compound according to claim 1, wherein substituents on the aryl or heteroaryl group are one or more of halo, hydroxy, oxo, amino, amido, carboxy, nitro, thio, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C6-C20-aryl, C7-C24-alkaryl, C1-C20-alkoxy, C2-C20-alkenoxy, C2-C20-alkynoxy, C6-C20-aryloxy, C1-C20-alkylamino, C2-C40-dialkylamino, C1-C20-alkamido, C2-C20-carboxy or C1-C20-carbonyl.
4:
- The compound according to claim 1, wherein the aryl groups are phenyl, naphthyl or anthracyl and the heteroaryl groups are pyridinyl, pyridazinyl, pyrimidyl, pyrazyl, triazinyl, pyrrolyl, pyrazolyl, imidazolyl, (1,2,3)-triazolyl, (1,2,4)-triazolyl, pyrazinyl, pyrimidinyl, tetrazolyl, furyl, thienyl, isoxazolyl, thiazolyl, isoxazolyl, oxazolyl, benzofuranyl, benzothiophenyl, indolyl, 1H-indazolyl, indolinyl, benzopyrazolyl, 1,3-benzodioxolyl, benzoxazolyl, purinyl, tetralinyl, coumarinyl, chromonyl, quinolinyl, isoquinolinyl, benzimidazolyl, quinazolinyl, pyrido[2,3-b]pyrazinyl, pyrido[3,2-c]pyridazinyl, pyrido[3,4-b]-pyridinyl, 2(1H)-quinolonyl, 1(2H)-isoquinolonyl, 1,4-benzisoxazinyl, naphthyridinyl, benzothiazolyl, quinoxalinyl, benzoxazinyl, phthalazinyl or cinnolinyl.
5:
- The compound according to claim 1, wherein X1 and X2 are the same or different and each is independently Br, thienyl, brominated thienyl, C1-C20-alkyl substituted thienyl or C1-C20-alkyl substituted brominated thienyl.
6:
- The compound according to claim 1, wherein X1 and X2 are the same and are Br, brominated thienyl or octyl substituted brominated thienyl.
7:
- The compound according to claim 1, wherein R1 and R2 are independently H, C1-C20-alkyl, C2-C20-alkenyl, C2-C20-alkynyl, C6-C20-aryl, C7-C24-alkaryl, C1-C20-alkoxy, C2-C20-alkenoxy, C2-C20-alkynoxy, C6-C20-aryloxy, C1-C20-alkylamino, C2-C40-dialkylamino, C1-C20-alkamido, C2-C20-carboxy or C1-C20-carbonyl, or R1 and/or R2 taken together with Y form a C6-C20-carbocyclic or C3-C24-heterocyclic group.
8:
- The compound according to claim 1, wherein Y is S.
9:
- The compound according to claim 1, wherein Y is Se.
10:
- An oligomer or polymer comprising an electron-accepting monomer of Formula (I) as defined in claim 1 copolymerized with an electron-donating co-monomer.
11:
- The oligomer or polymer according to claim 10, wherein the electron-donating co-monomer is one or more of a substituted or unsubstituted phenyl, thiene, fluorene, carbazole, benzodithiophene, pyrrole, indenofluorene, indolocarbazole, dibenzosilole, dithienosilole, benzo[1,2-b;3,4-b]dithiophene, benzo[2,1-b:3,4-b′]dithiophene, cyclopenta[2,1-b:3,4-b′]dithiophene, thieno[3,2-b]thiophene, thieno[3,4-b]thiophene or dithieno[3,2-b:2′,3′-d]pyrrole, where the substituent, if present, is one or more of Cl, Br, I, a C6-C18-aryl group or a C3-C14-heteroaryl group having one or more of N, O or S in the ring.
12:
- The oligomer or polymer according to claim 10, wherein the electron-donating co-monomer is fluorene, carbazole or benzodithiophene.
13:
- The oligomer or polymer according to claim 10, further comprising one or more electron-accepting monomers other than the monomer of Formula (I).
14:
- The oligomer or polymer according to claim 13, wherein the one or more electron-accepting monomers other than the monomer of Formula (I) is a substituted or unsubstituted benzothiadiazole, thienopyrazine, quinoxaline, dihydropyrrolo[3,4-]pyrrole-1,4-dione, thieno[3,4-b]thiophene, where the substituent, if present, is one or more of Cl, Br, I, a C6-C18-aryl group or a C3-C14-heteroaryl group having one or more of N, O or S in the ring.
15:
- The oligomer or polymer according to claim 10 having a ratio of electron-accepting monomer to electron-donating co-monomer in a range of from 1:99 to 99:1 mol %.
16:
- The oligomer or polymer according to claim 10 having a ratio of electron-accepting monomer to electron-donating co-monomer in a range of from 40:60 to 60:40 mol %.
17:
- The oligomer or polymer according to claim 10, comprising from 2 to 20,000 monomeric units.
18:
- The oligomer or polymer according to claim 10, comprising from 10 to 10,000 monomeric units.
19:
- A film or membrane comprising the oligomer or polymer as defined in claim 10.
20-23. (canceled)
24:
- A process for producing a compound of Formula (I) as defined in claim 1 comprising: