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US 9,315,617 B2Granted
Crosslinkable and crosslinked polymers, method for the production thereof, and use thereof
AssigneeMerck Patent GmbH
InventorsFrank Egon Meyer, Niels Schulte, René Peter Scheurich, Rémi Manouk Anémian, Aurélie Ludemann, Alice Julliart
Life of this patent
Estimating the term…
Abstract
The present invention relates to cross-linkable and cross-linked polymers and to a method for the production thereof. The invention further relates to the use of said polymers in electronic devices and to the corresponding electronic devices themselves.
Claims13
Polymer containing at least one structural unit of the general formula I,
- wherein
- Z is an aromatic or an heteroaromatic ring system, optionally substituted by one or more radical R, wherein the aromatic or heteroaromatic ring system is selected from the group consisting of benzene, naphthalene, anthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, fluorubin, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, benzothiadiazole, benzanthrene, benzanthracene, rubicene and triphenylene,
- R is selected on each occurrence, independently of one another, from F, Cl, Br, I, N(Ar)2, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)Ar, C(═O)R2, P(═O)(Ar)2, P(═O)(R2)2, S(═O)Ar, S(═O)R2, S(═O)2Ar, S(═O)2R2, CR2═CR2Ar, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which optionally substituted by one or more radicals R2, where in the straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or in the branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms one or more non-adjacent CH2 groups optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where in the straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or in the branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms one or more H atoms optionally replaced by F, Cl, Br, I, CN or NO2, where two or more substituents R optionally form a mono- or polycyclic, or aromatic ring system with one another, where R2 is in each case, independently of one another, H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 C atoms,
- X is selected from a direct bond, a linear or branched alkylene group having 1 to 20 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced by —O—, —S—, —NH—, —N(CH3)—, —N—CO—, —N—CO—O—, —N—CO—, N, —CO—, —O—CO—, —S—CO—, —O—COO—, —CO—S—, —CO—O—, —CH(halogen)-, —CH(CN)—, —CH═CH— or —C≡C—, or a cyclic alkyl group,
- Ar1 and Ar2
- are an optionally substituted aryl or an optionally substituted heteroaryl group, which are optionally linked to one another,
- Q is a crosslinkable group,
- R1 is a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or a silyl group or substituted keto group having 1 to 40 C atoms, or an optionally substituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, or Ar2, where one or more H atoms is optionally replaced by fluorine,
- n is 1, 2, 3 or 4, and
- the dashed lines represent the linking in the polymer,
- wherein if n=1 or if Z=fluorene and n=2, X is not a direct bond.
8 more elements
A compound of formula II,
- wherein
- Z is an aromatic or an heteroaromatic ring system, optionally substituted by one or more radical R, wherein the aromatic or heteroaromatic ring system is selected from the group consisting of benzene, naphthalene, anthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazaperylene, pyrazine, phenazine, fluorubin, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazine, purine, pteridine, indolizine, benzothiadiazole, benzanthrene, benzanthracene, rubicene and triphenylene,
- R is selected on each occurrence, independently of one another, from F, Cl, Br, I, N(Ar)2, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)Ar, C(═O)R2, P(═O)(Ar)2, P(═O)(R2)2, S(═O)Ar, S(═O)R2, S(═O)2Ar, S(═O)2R2, CR2═CR2Ar, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which optionally substituted by one or more radicals R2, where in the straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or in the branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms one or more non-adjacent CH2 groups optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where in the straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or in the branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms one or more H atoms optionally replaced by F, Cl, Br, I, CN or NO2, where two or more substituents R optionally form a mono- or polycyclic, aliphatic or aromatic ring system with one another, where R2 is in each case, independently of one another, H or an aliphatic or aromatic hydrocarbon radical having 1 to 20 C atoms,
- X is selected from a direct bond, a linear or branched alkylene group having 1 to 20 C atoms, in which one or more non-adjacent CH2 groups are optionally replaced by —O—, —S—, —NH—, —N(CH3)—, —N—CO—, —N—CO—O—, —N—CO—, N, —CO—, —O—CO—, —S—CO—, —O—COO—, —CO—S—, —CO—O—, —CH(halogen)-, —CH(CN)—, —CH═CH— or —C≡C—, or a cyclic alkyl group,
- Ar1 and Ar2
- are an optionally substituted aryl or an optionally substituted heteroaryl group, which are optionally linked to one another,
- Q is a crosslinkable group,
- R1 is a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms or a silyl group or substituted keto group having 1 to 40 C atoms, or an optionally substituted aromatic or heteroaromatic ring system having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems, or Ar2, where one or more H atoms is optionally replaced by fluorine,
- Y1 and Y1′
- are each leaving groups,
- n is 1, 2, 3 or 4, and
- wherein if n=1 or if Z=fluorene and n=2, X is not a direct bond.
9 more elements
Dependencies are inferred from the claim text.