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US 2007/0185303 A1Published application
Compounds for organic electronic devices
AssigneeMerck Patent GmbH Patents & Scientific Information
InventorsPhilipp Stossel, Horst Vestweber, Holger Heil, Esther Breuning
Life of this patent
Estimating the term…
Abstract
The present invention relates to the improvement of organic electroluminescent devices, in particular blue-emitting devices, by using compounds of the formula (1) as dopants in the emitting layer.
Claims23
1-21. (canceled)
Compounds of the formula (1)
- wherein:
- Y is on each occurrence P, As, Sb, Bi, O, S, Se, or Te, and wherein when Y═O, X is a free electron pair, and wherein when Y═S, Se, or Te, X, identically or differently on each occurrence, is a free electron pair or O;
- X is on each occurrence, identically or differently, O, S, Se, Te, or a free electron pair;
- Ar1 and Ar2
- are on each occurrence, identically or differently, an aryl group having 6 to 24 C atoms or a heteroaryl group having 2 to 24 C atoms, wherein said aryl group and heteroaryl group is optionally substituted by one or more radicals R10;
- R1 and R2
- are on each occurrence, identically or differently, H, CN, F, a straight-chain alkyl group having up to 40 C atoms, a branched alkyl group having 3 to 40 C atoms, or a cyclic alkyl group having 3 to 40 C atoms, wherein said straight-chain, branched, and cyclic alkyl groups are optionally substituted by one or more radicals R20, and wherein one or more non-adjacent CH2 groups in said straight-chain, branched, and cyclic alkyl groups are, independently of one another, optionally replaced by —R20C═CR20—, —C≡C—, Si(R20)2, Ge(R20)2, Sn(R20)2, C═O, C═S, C═Se, C═NR20, —O—, —S—, —COOR20— or —CONR20—, and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, SCN, NO2, an aromatic system having 6 to 40 aromatic C atoms, a heteroaromatic system having 2 to 40 aromatic C atoms, an aryloxy group having 6 to 40 aromatic C atoms or a heteroaryloxy group having 2 to 40 aromatic C atoms, wherein said aromatic system, heteroaromatic system, aryloxy group and heteroaryloxy group are optionally substituted by one or more radicals R10, and wherein R1 and R2, independently of one another, optionally define a cyclic system together with Ar1 and/or Ar2;
- R10 is on each occurrence, identically or differently, H, F, Cl, Br, I, CN, NO2, a straight-chain alkyl group having up to 40 C atoms, a branched alkyl group having 3 to 40 C atoms, or a cyclic alkyl group having 3 to 40 C atoms, wherein said straight-chain, branched, and cyclic alkyl groups are optionally substituted by one or more radicals R20, and wherein one or more non-adjacent CH2 groups in said straight-chain, branched, and cyclic alkyl groups are, independently of one another, optionally replaced by —R20C═CR20—, —C≡C—, Si(R20)2, Ge(R20)2, Sn(R20)2, C═O, C═S, C═Se, C═NR20, —O—, —S—, —COOR20— or —CONR20— and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, NO2, an aryl group having 6 to 24 C atoms, a heteroaryl group having 2 to 24 C atoms, an aryloxy group having 6 to 24 aromatic C atoms, a heteroaryloxy group having 2 to 24 aromatic C atoms, wherein said aromatic system, heteroaromatic system, aryloxy group and heteroaryloxy group are optionally substituted by one or more radicals R20, or a combination of two, three, four or five of these systems;
- and wherein two or more substituents R10, on the same ring and/or on different rings, optionally define a monocyclic or polycyclic aliphatic ring system or a monocyclic or polycyclic aromatic ring system with one another or together with R1 and/or R2;
- R20 is on each occurrence, identically or differently, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- n is, identically or differently on each occurrence, 0, 1, 2, 3, 4 or 5;
- m is, identically or differently on each occurrence, 0, 1, 2, 3, 4 or 5;
- q is, identically or differently on each occurrence, 0, 1, 2, 3, 4 or 5, with the proviso that at least one q is does not equal 0;
- p is 2 when Y is an element from main group 6 of the Periodic Table and is 3 when Y is an element from main group 5 of the Periodic Table;
- z is 1 when Y is an element from main group 5 of the Periodic Table and is 2 when Y is an element from main group 6 of the Periodic Table;
- and
- with the proviso that said compounds of formula (1) do not comprise
14 more elements
Mixtures comprising at least one compound of the formula (1)
- wherein
- Y is on each occurrence P, As, Sb, Bi, O, S, Se, or Te, and wherein when Y═O, X is a free electron pair, and wherein when Y═S, Se or Te, X, identically or differently on each occurrence, is a free electron pair or O;
- X is on each occurrence, identically or differently, O, S, Se, Te, or a free electron pair;
- Ar1 and Ar2
- are on each occurrence, identically or differently, an aryl group having 6 to 24 C atoms or a heteroaryl group having 2 to 24 C atoms, wherein said aryl group and heteroaryl group is optionally substituted by one or more radicals R10;
- R1 and R2
- are on each occurrence, identically or differently, H, CN, F, a straight-chain alkyl group having up to 40 C atoms, a branched alkyl group having 3 to 40 C atoms, or a cyclic alkyl group having 3 to 40 C atoms, wherein said straight-chain, branched, and cyclic alkyl groups are optionally substituted by one or more radicals R20, and wherein one or more non-adjacent CH2 groups in said straight-chain, branched, and cyclic alkyl groups are, independently of one another, optionally replaced by —R20C═CR20—, —C≡C—, Si(R20)2, Ge(R20)2, Sn(R20)2, C═O, C═S, C═Se, C═NR20, —O—, —S—, —COOR20— or —CONR20—, and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, SCN, NO2, an aromatic system having 6 to 40 aromatic C atoms, a heteroaromatic system having 2 to 40 aromatic C atoms, an aryloxy group having 6 to 40 aromatic C atoms or a heteroaryloxy group having 2 to 40 aromatic C atoms, wherein said aromatic system, heteroaromatic system, aryloxy group and heteroaryloxy group are optionally substituted by one or more radicals R10, and wherein R1 and R2, independently of one another, optionally define a cyclic system together with Ar1 and/or Ar2;
- R10 is on each occurrence, identically or differently, H, F, Cl, Br, I, CN, NO2, a straight-chain alkyl group having up to 40 C atoms, a branched alkyl group having 3 to 40 C atoms, or a cyclic alkyl group having 3 to 40 C atoms, wherein said straight-chain, branched, and cyclic alkyl groups are optionally substituted by one or more radicals R20, and wherein one or more non-adjacent CH2 groups in said straight-chain, branched, and cyclic alkyl groups are, independently of one another, optionally replaced by —R20C═CR20—, —C≡C—, Si(R20)2, Ge(R20)2, Sn(R20)2, C═O, C═S, C═Se, C═NR20, —O—, —S—, —COOR20— or —CONR20— and wherein one or more H atoms are optionally replaced by F, Cl, Br, I, CN, NO2, an aryl group having 6 to 24 C atoms, a heteroaryl group having 2 to 24 C atoms, an aryloxy group having 6 to 24 aromatic C atoms, a heteroaryloxy group having 2 to 24 aromatic C atoms, wherein said aromatic system, heteroaromatic system, aryloxy group and heteroaryloxy group are optionally substituted by one or more radicals R20, or a combination of two, three, four or five of these systems;
- and wherein two or more substituents R10, on the same ring and/or on different rings, optionally define a monocyclic or polycyclic aliphatic ring system or a monocyclic or polycyclic aromatic ring system with one another or together with R1 and/or R2;
- R20 is on each occurrence, identically or differently, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- n is, identically or differently on each occurrence, 0, 1, 2, 3, 4 or 5;
- m is, identically or differently on each occurrence, 0, 1, 2, 3, 4 or 5;
- q is, identically or differently on each occurrence, 0, 1, 2, 3, 4 or 5, with the proviso that at least one q is does not equal 0;
- p is 2 when Y is an element from main group 6 of the Periodic Table and is 3 when Y is an element from main group 5 of the Periodic Table;
- z is 1 when Y is an element from main group 5 of the Periodic Table and is 2 when Y is an element from main group 6 of the Periodic Table;
- and
- at least one host material.
14 more elements
Dependencies are inferred from the claim text.