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US 7,323,533 B2Granted
Conjugated polymers containing spirobifluorene units and the use thereof
AssigneeCovion Organic Semiconductors GmbH
InventorsHeinrich Becker, Kevin Treacher, Hubert Spreitzer, Aurelie Falcou, Philipp Stössel, Arne Büsing, Amir Parham, Bernd Schröder
Life of this patent
Estimating the term…
Abstract
The present invention relates to novel conjugated polymers comprising spirobifluorene units and their use in optoelectronic devices, preferably in, for example, displays based on polymeric organic light-emitting diodes.
Claims22
A conjugated polymer comprising units of the formula (I)
- together with one or more units selected from the following groups:
- group 1:
- units which significantly increase the hole injection or transport properties of the polymers;
- group 2:
- units which significantly increase the electron injection or transport properties of the polymers;
- group 3:
- units which comprise combinations of individual units of group 1 and group 2;
- group 4:
- units which alter the emission characteristics so that phosphorescence can be obtained instead of fluorescence;
- wherein
- X is identical or different on each occurrence and is in each case CH, CR1 or N,
- Z is identical or different on each occurrence and is in each case a single chemical bond, a CR3R4 group, a —CR3R4—CR3R4— group, a —CR3═CR4— group, O, S, N—R5, C═O, C═CR3R4 or SiR3R4;
- R1 is identical or different on each occurrence and is in each case a linear, branched or cyclic alkyl or alkoxy chain which has from 1 to 22 carbon atoms and in which one or more nonadjacent carbon atoms is optionally replaced by N—R5, O, S, —CO—O—, O—CO—O, where one or more H atoms is optionally replaced by fluorine, or is an aryl or aryloxy group which has from 5 to 40 carbon atoms and in which one or more carbon atoms is optionally replaced by O, S or N, which is optionally substituted by one or more nonaromatic radicals R1, or is Cl, F, CN, N(R5)2, N(R5)3+, where two or more radicals R1 together form a ring system;
- R2 is identical or different on each occurrence and is in each case a linear, branched or cyclic alkyl or alkoxy chain which has from 1 to 22 carbon atoms and in which one or more nonadjacent carbon atoms is optionally replaced by N—R5, O, S, —CO—O—, O—CO—O, where one or more H atoms is optionally replaced by fluorine, or is an aryl or aryloxy group which has from 5 to 40 carbon atoms and in which one or more carbon atoms is optionally replaced by O, S or N which is optionally substituted by one or more nonaromatic radicals R1, or is CN;
- R3 and R4 are identical or different on each occurrence and are each H, a linear, branched or cyclic alkyl chain which has from 1 to 22 carbon atoms and in which one or more nonadjacent carbon atoms is optionally replaced by N—R5, O, S, —CO—O—, O—CO—O, where one or more H atoms is optionally replaced by fluorine, or are each an aryl group which has from 5 to 40 carbon atoms and in which one or more carbon atoms is optionally replaced by O, S or N, which is optionally substituted by one or more nonaromatic radicals R1, or are each CN;
- where a plurality of adjacent radicals R3 and/or R4 may together also form a ring;
- R5 is identical or different on each occurrence and is in each case H, a linear, branched or cyclic alkyl chain which has from 1 to 22 carbon atoms and in which one or more nonadjacent carbon atoms is optionally replaced by O, S, —CO—O—, O—CO—O, where one or more H atoms is optionally replaced by fluorine, or is an aryl group which has from 5 to 40 carbon atoms and in which one or more carbon atoms is optionally replaced by O, S or N, which is optionally substituted by one or more nonaromatic radicals R1;
- m is identical or different on each occurrence and is in each case 0, 1, 2, or 3;
- n is identical or different on each occurrence and is in each case 0, 1, 2, 3 or 4;
- with the proviso that repeating units of the formula (I) and units of groups 1 to 4 together make up at least 40% of all repeating units in the polymer and that the ratio of repeating units of the formula (I) to the sum of those of groups 1 to 4 is in the range from 20:1 to 1:2;
- wherein the units of group 1 are selected from among the units of the formulae (II) to (XIX):
- wherein
- R1, R2, R4, R5, n, and m
- are as defined for units of the formula (I);
- A1, A2, and Ar3
- are, identically or differently on each occurrence, aromatic or
- heteroaromatic hydrocarbons having from 2 to 40 carbon atoms and are optionally substituted by one or more nonaromatic radicals R1;
- and
- o is 1, 2, or 3;
- and
- wherein the units of group 2 are selected from among the units of the formulae (XX) to (XXX):
- wherein
- R1, m, and n
- are as defined for units of the formula (I);
- and
- p is 0, 1 or 2.
33 more elements
A conjugated polymer comprising at least 3 different units, at least one of which is of the formula (I)
- and
- at least one of which is selected from the following groups:
- group 1:
- units which significantly increase the hole injection or transport properties of the polymers;
- group 2:
- units which significantly increase the electron injection or transport properties of the polymers;
- group 3:
- units which comprise combinations of individual units of group 1 and group 2;
- group 4:
- units which alter the emission characteristics so that phosphorescence can be obtained instead of fluorescence;
- wherein
- X is, identically or differently on each occurrence, CH, CR1, or N;
- Z is, identically or differently on each occurrence, a single chemical bond, a CR3R4 group, a —CR3R4—CR3R4 group, a —CR3═CR4— group, O, S, N—R5, C═O, C═CR3R4, or SiR3R4;
- R1 is, identically or differently on each occurrence, a linear, branched, or cyclic alkyl or alkoxy chain having up to 22 carbon atoms, wherein one or more nonadjacent carbon atoms is optionally replaced by N—R5, O, S, —CO—O—, or O—CO—O, and wherein one or more H atoms is optionally replaced by fluorine;
- or is an aryl or aryloxy group having from 5 to 40 carbon atoms, wherein one or more carbon atoms is optionally replaced by O, S or N, and is optionally substituted by one or more nonaromatic radicals R1;
- or is Cl, F, CN, N(R5)2, or N(R5)3+;
- and wherein two or more radicals R1 optionally define a ring system;
- R2 is, identically on each occurrence, a linear, branched or cyclic alkyl or alkoxy chain having up to 22 carbon atoms, wherein one or more nonadjacent carbon atoms is optionally replaced by N—R5, O, S, —CO—O—, or O—CO—O, and wherein one or more H atoms is optionally replaced by fluorine;
- or is an aryl or aryloxy group having from 5 to 40 carbon atoms, wherein one or more carbon atoms is optionally replaced by O, S or N and is optionally substituted by one or more nonaromatic radicals R1;
- or is CN;
- R3 and R4 are, identically or differently on each occurrence, H, a linear, branched or cyclic alkyl chain having up to 22 carbon atoms, wherein one or more nonadjacent carbon atoms is optionally replaced by N—R5, O, S, —CO—O—, or O—CO—O, and wherein one or more H atoms is optionally replaced by fluorine;
- or are each an aryl group having from 5 to 40 carbon atoms, wherein one or more carbon atoms is optionally replaced by O, S or N, and is optionally substituted by one or more nonaromatic radicals R1;
- or are each CN;
- and wherein a plurality of adjacent radicals R3 and/or R4 optionally define a ring;
- R5 it is, identically or differently on each occurrence, H, a linear, branched or cyclic alkyl chain having up to 22 carbon atoms, wherein one or more nonadjacent carbon atoms is optionally replaced by O, S, —CO—O—, or O—CO—O, and wherein one or more H atoms is optionally replaced by fluorine;
- or is an aryl group having from 5 to 40 carbon atoms, wherein one or more carbon atoms is optionally replaced by O, S or N, and is optionally substituted by one or more nonaromatic radicals R1;
- m is, identically or differently on each occurrence, 0, 1, 2, or 3;
- n is, identically or differently on each occurrence, 0, 1, 2, 3 or 4;
- with the proviso that repeating units of the formula (I) and units of groups 1 to 4 together make up at least 40% of all repeating units in the polymer and that the ratio of repeating units of the formula (I) to the sum of those of groups 1 to 4 is in the range from 20:1 to 1:2.
26 more elements
Dependencies are inferred from the claim text.