Organic electroluminescent devices
AssigneeMerck Patent GmbH
InventorsHorst Vestweber, Philipp Stoessel, Holger Heil
Life of this patent
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Abstract
The present invention relates to mixtures of organic materials, to the use of these mixtures in organic electroluminescent devices, and to organic electroluminescent devices comprising these mixtures.
Claims23
An organic electroluminescent device comprising an anode, a cathode and at least one organic layer, wherein said at least one organic layer comprises:
- at least one compound of formula (1)
- wherein
- Ar1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R1;
- Ar2 is, identically or differently on each occurrence, a divalent arylene or heteroarylene group having 5 to 20 aromatic ring atoms optionally substituted by one or more radicals R1;
- R1 is, identically or differently on each occurrence, H;
- F;
- Cl;
- Br;
- I;
- CN;
- Si(R3)3;
- B(OR3)2;
- a straight-chain alkyl, alkoxy, or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3—, and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3—, and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R3;
- or a combination of two, three, four or five of these systems;
- and wherein two or more substituents R1 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- and
- at least one compound of formula (2) or formula (3)
- wherein
- Ar3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R2;
- X is, identically or differently on each occurrence, a divalent group containing up to 40 C atoms, —O—, —S—, —NH—, or a single bond;
- R2 and R4
- are, identically or differently on each occurrence, H;
- F;
- Cl;
- Br;
- I;
- CN;
- N(R3)2;
- a straight-chain alkyl, alkoxy, or thioalkoxy group having up to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3— and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3— and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R3;
- or a combination of two, three, four or five of these systems;
- and wherein two or more adjacent substituents R4 optionally define a mono- or polycyclic, aliphatic ring system with one another;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- and
- n is, identically or differently on each occurrence, 0, 1, 2, 3, or 4;
- wherein said at least one organic layer is an emitting layer;
- wherein said at least one compound of formula (1) is present in said emitting layer as a dopant in an amount of from 1.0 to 20.0% by weight;
- and
- wherein said at least one compound of formula (2) or formula (3) is present in said emitting layer as a host in an amount of from 80.0 to 99.0% by weight.
A mixture comprising at least one compound of formula (1)
- wherein
- Ar1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R1;
- Ar2 is, identically or differently on each occurrence, a divalent arylene or heteroarylene group having 5 to 20 aromatic ring atoms optionally substituted by one or more radicals R1;
- R1 is, identically or differently on each occurrence, H;
- F;
- Cl;
- Br;
- I;
- CN;
- Si(R3)3;
- B(OR3)2;
- a straight-chain alkyl, alkoxy, or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3—, and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C=Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3—, and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R3;
- or a combination of two, three, four or five of these systems;
- and wherein two or more substituents R1 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- and
- at least one compound of formula (3)
- wherein
- Ar3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R2;
- X is, identically or differently on each occurrence, a divalent group containing up to 40 C atoms, —O—, —S—, —NH—, or a single bond;
- R2 and R4
- are, identically or differently on each occurrence, H;
- F;
- Cl;
- Br;
- I;
- CN;
- N(R3)2;
- a straight-chain alkyl, alkoxy, or thioalkoxy group having up to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3— and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3— and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R3;
- or a combination of two, three, four or five of these systems;
- and wherein two or more adjacent substituents R4 optionally define a mono- or polycyclic, aliphatic ring system with one another;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- and
- n is, identically or differently on each occurrence, 0, 1, 2, 3, or 4;
- wherein said at least one compound of formula (1) is present in said mixture as a dopant in an amount of from 1.0 to 20.0% by weight;
- and
- wherein said at least one compound of formula (2) or formula (3) is present in said mixture as a host in an amount of from 80.0 to 99.0% by weight.
An organic electroluminescent device comprising an emitting layer comprising a mixture comprising at least one compound of formula (1)
- wherein
- Ar1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R1;
- Ar2 is, identically or differently on each occurrence, a divalent arylene or heteroarylene group having 5 to 20 aromatic ring atoms optionally substituted by one or more radicals R1;
- R1 is, identically or differently on each occurrence, H;
- F;
- Cl;
- Br;
- I;
- CN;
- Si(R3)3;
- B(OR3)2;
- a straight-chain alkyl, alkoxy, or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3—, and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3—, and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R3;
- or a combination of two, three, four or five of these systems;
- and wherein two or more substituents R1 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- and at least one compound of formula (2) or formula (3)
- wherein
- Ar3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R2;
- X is, identically or differently on each occurrence, a divalent group containing up to 40 C atoms, —O—, —S—, —NH—, or a single bond;
- R2 and R4 are, identically or differently on each occurrence, H;
- F;
- Cl;
- Br;
- I;
- CN;
- N(R3)2;
- a straight-chain alkyl, alkoxy, or thioalkoxy group having up to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3— and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3— and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R3;
- or a combination of two, three, four or five of these systems;
- and wherein two or more adjacent substituents R4 optionally define a mono- or polycyclic, aliphatic ring system with one another;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- and
- n is, identically or differently on each occurrence, 0, 1, 2, 3, or 4;
- wherein said at least one compound of formula (1) is present in said mixture as a dopant in an amount of from 1.0 to 20.0% by weight;
- and
- wherein said at least one compound of formula (2) or formula (3) is present in said mixture as a host in an amount of from 80.0 to 99.0% by weight.
An organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic integrated circuit, an organic solar cell, an organic field-quench device, an organic photoreceptor, or an organic laser diode comprising an emitting layer comprising a mixture comprising at least one compound of formula (1)
- wherein
- Ar1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R1;
- Ar2 is, identically or differently on each occurrence, a divalent arylene or heteroarylene group having 5 to 20 aromatic ring atoms optionally substituted by one or more radicals R1;
- R1 is, identically or differently on each occurrence, H;
- F;
- Cl;
- Br;
- I;
- CN;
- Si(R3)3;
- B(OR3)2;
- a straight-chain alkyl, alkoxy, or thioalkoxy group having up to 40 C atoms optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3—, and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3—, and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R3;
- or a combination of two, three, four or five of these systems;
- and wherein two or more substituents R1 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- and
- at least one compound of formula (2) or formula (3)
- wherein
- Ar3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R2;
- X is, identically or differently on each occurrence, a divalent group containing up to 40 C atoms, —O—, —S—, —NH—, or a single bond;
- R2 and R4 are, identically or differently on each occurrence, H;
- F;
- Cl;
- Br;
- I;
- CN;
- N(R3)2;
- a straight-chain alkyl, alkoxy, or thioalkoxy group having up to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3— and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- a branched or cyclic alkyl, alkoxy, or thioalkoxy group having 3 to 40 C atoms, optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups is optionally replaced by —R3C═CR3—, —C≡C—, Si(R3)2, Ge(R3)2, Sn(R3)2, C═O, C═S, C═Se, C═NR3, —O—, —S—, —N(R3)—, or —CONR3— and wherein one or more H atoms is optionally replaced by F, Cl, Br, I, CN, or NO2;
- an aryl or heteroaryl group having 5 to 30 aromatic ring atoms optionally substituted by one or more radicals R3, or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms optionally substituted by one or more radicals R3;
- or a combination of two, three, four or five of these systems;
- and wherein two or more adjacent substituents R4 optionally define a mono- or polycyclic, aliphatic ring system with one another;
- R3 is, identically or differently on each occurrence, H or an aliphatic or aromatic hydrocarbon radical having up to 20 C atoms;
- wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
- and
- n is, identically or differently on each occurrence, 0, 1, 2, 3, or 4;
- wherein said at least one compound of formula (1) is present in said mixture as a dopant in an amount of from 1.0 to 20.0% by weight;
- and
- wherein said at least one compound of formula (2) or formula (3) is present in said mixture as a host in an amount of from 80.0 to 99.0% by weight.
Dependencies are inferred from the claim text.