Use of thianthrene-containing polymers as a charge store
US-2019229335-A1 · Jul 25, 2019 · US
US11639403B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-11639403-B2 |
| Application number | US-201916679540-A |
| Country | US |
| Kind code | B2 |
| Filing date | Nov 11, 2019 |
| Priority date | Nov 9, 2018 |
| Publication date | May 2, 2023 |
| Grant date | May 2, 2023 |
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A polymer includes a repeating unit represented by at least one of Formula 1a or Formula 1b: wherein, in Formulae 1a or 1b, CY 1 is a group represented by at least one of Formula 1-2 or Formula 1-4, CY 2 is a group represented by Formula 1-3, and L 1 , L 2 , a1, and a2 are defined the same as in the specification, and in Formulae 1-2, Formula 1-3, or 1-4, X, Y, R 1 , R 2 , R 11 to R 14 , b1, b2, R 21 , R 22 , b21, b22, Z 1 , Z 2 , c1, and c2 are defined the same as in the specification.
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What is claimed is: 1. A polymer comprising: a repeating unit represented by at least one of Formula 1a or Formula 1b wherein, in Formulae 1a and 1b, CY 1 is a group represented by at least one of Formula 1-2 or Formula 1-4, CY 2 is a group represented by Formula 1-3, L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, or a substituted or unsubstituted C 2 -C 20 alkynylene group, and a1 and a2 are each independently an integer from 1 to 5, and two or more L 1 are the same or different from one another when a1 is 2 or greater, and two or more L 2 are the same or different from each other when a2 is 2 or greater, wherein, in Formulae 1-2 and 1-3, X and Y are each independently O or S, R 1 , R 2 , and R 11 to R 14 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, b1 and b2 are each independently an integer from 1 to 3, and two or more R 1 are the same or different from one another when b1 is 2 or greater, and two or more R 2 are the same or different from one another when b2 is 2 or greater, and in Formula 1-4, R 21 and R 22 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, b21 and b22 are each independently an integer from 0 to 3, and two or more R 21 are the same or different from one another when b21 is 2 or greater, and two or more R 22 are the same or different from one another when b22 is 2 or greater, Z 1 and Z 2 are each independently an electron withdrawing group, C1 and c2 are each independently an integer of 1 to 4, the sum of b21and c1 is 4, the sum of b22 and c2 is 4, is a binding site to L 1 in Formulae 1a and 1b, and is a binding site to L 2 in Formula 1b. 2. The polymer of claim 1 , wherein, in Formula 1a, L 1 is a single bond, a methylene group, an ethylene group, a propylene group, a butylene group, or a pentylene group; or a methylene group, an ethylene group, a propylene group, a butylene group, and a pentylene group, each of which is substituted with at least one of deuterium, a halogen, or a C 1 -C 5 alkyl group. 3. The polymer of claim 1 , wherein, in Formulae 1-2 and 1-3, X and Y are the same. 4. The polymer of claim 1 , wherein, in Formulae 1-2 and 1-3, R 1 and R 2 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a sec-pentyl group, 3-pentyl group, or a sec-isopentyl group; or a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a sec-pentyl group, 3-pentyl group, and a sec-isopentyl group, each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a phosphoric acid group or a salt thereof. 5. The polymer of claim 1 , wherein the group represented by Formula 1-2 is represented by at least one of Formula 1-2-1, Formula 1-2-2, Formula 1-2-3, or Formula 1-2-4 wherein, in Formula 1-2-1 to Formula 1-2-4, R 1 , b 1 , and R 11 to R 14 are defined the same as those of claim 1 . 6. The polymer of claim 1 , wherein the group represented by Formula 1-3 is represented by at least one of Formula 1-3-1, Formula 1-3-2, Formula 1-3-3, Formula 1-3-4, Formula 1-3-5, Formula 1-3-6, Formula 1-3-7, or Formula 1-3-8 wherein, in Formula 1-3-1 to Formula 1-3-8, R 1 , R 2 , b1, and b2 are defined the same as those of claim 1 . 7. The polymer of claim 1 , wherein, in Formula 1-4, R 21 and R 22 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a sec-pentyl group, 3-pentyl group, or a sec-isopentyl group; or a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a sec-pentyl group, 3-pentyl group, and a sec-isopentyl group, each of which is substituted with at least one of deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, a carboxylic acid group or a salt thereof, a
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