# US 8,785,001 B2 · Organic electroluminescent devices > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,785,001 B2 - Document ID: US8785001B2 - Status: Granted - Kind: B2 - Application number: 12/096,492 - Filed: 2006-11-17 - Published: 2008-12-04 - Granted: 2014-07-22 - Earliest claimed: 2005-12-08 - Assignees: Merck Patent GmbH - Applicants: Horst Vestweber; Philipp Stoessel; Holger Heil - Inventors: Horst Vestweber; Philipp Stoessel; Holger Heil - Web page: https://patentgrep.com/patent/US8785001B2 ## CPC - H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine} - C09K 11/06: containing organic luminescent materials - H05B 33/14: characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} - H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene} - H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom} - H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom} - C09K 2211/1011: Condensed systems - C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B - H10K 50/11: characterised by the electroluminescent [EL] layers - H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene - H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole} - H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes} - H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene} - Y02E 10/549: Organic PV cells - Y10S 428/917: Electroluminescent - H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - H05B: ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL - Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## 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. ## Claims ### Claim 1 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. ### Claim 2 (depends on 1) The organic electroluminescent device of claim 1, wherein said device comprises at least one compound of formula (1a) wherein the phenylene groups are optionally substituted by one or more radicals R1. ### Claim 3 (depends on 1) The organic electroluminescent device of claim 1, wherein Ar1 is, identically or differently on each occurrence, an aryl or heteroaryl group having 6 to 14 C atoms optionally substituted by one or more radicals R1. ### Claim 4 (depends on 3) The organic electroluminescent device of claim 3, wherein Ar1 is, identically or differently on each occurrence, an aryl group having 6 to 14 C atoms optionally substituted by one or more radicals R1. ### Claim 5 (depends on 1) The organic electroluminescent device of claim 1, wherein Ar1 is a phenyl, 1-naphthyl, or 2-naphthyl group, each of which is optionally substituted by one or more radicals R1. ### Claim 6 (depends on 1) The organic electroluminescent device of claim 1, wherein R1 is bonded to Ar1 in the para-position to the double bond. ### Claim 7 (depends on 1) The organic electroluminescent device of claim 1, wherein R1 is selected from the group consisting of H; F; Si(R3)3; B(OR3)2; straight-chain alkyl or alkoxy groups having up to 6 C atoms, wherein one or more CH2 groups are optionally replaced by —R3C═CR3—, Si(R3)2, —O—, —S— or —N(R3)— and wherein one or more H atoms are optionally replaced by F; branched or cyclic alkyl or alkoxy groups having 3 to 10 C atoms, wherein one or more CH2 groups are optionally replaced by —R3C═CR3—, Si(R3)2, —O—, —S— or —N(R3)— and wherein one or more H atoms are optionally replaced by F; or aryl or heteroaryl groups having 5 to 14 aromatic ring atoms; or a combination of two or three of these systems. ### Claim 8 (depends on 1) The organic electroluminescent device of claim 1, wherein the compounds of the formula (1) have a threefold axis of symmetry. ### Claim 9 (depends on 1) The organic electroluminescent device of claim 1, wherein Ar3 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 10 to 25 aromatic ring atoms optionally substituted by one or more radicals R2. ### Claim 10 (depends on 1) The organic electroluminescent device of claim 1, wherein Ar3 is, identically or differently on each occurrence, a 1-naphthyl, 2-naphthyl, 9-anthryl, 2-phenanthrenyl, 9-phenanthrenyl, quinolinyl, isoquinolinyl, ortho-biphenyl, 2-fluorenyl, or 2-spirobifluorenyl group, each of which is optionally substituted by one or more radicals R2. ### Claim 11 (depends on 1) The organic electroluminescent device of claim 1, wherein R2 is, identically or differently on each occurrence, H; F; B(OR3)2; a straight-chain alkyl or alkoxy group having up to 6 C atoms wherein each case one or more CH2 groups are optionally replaced by —R3C═CR3—, Si(R3)2, —O—, —S— or —N(R3)— and where one or more H atoms are optionally replaced by F; a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, wherein each case one or more CH2 groups are optionally replaced by —R3C═CR3—, Si(R3)2, —O—, —S— or —N(R3)— and where one or more H atoms are optionally replaced by F; or an aryl or heteroaryl group having 5 to 14 aromatic ring atoms; or a combination of two or three of these systems; and wherein two or more adjacent radicals R2 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another. ### Claim 12 (depends on 1) The organic electroluminescent device of claim 1, wherein X is, identically or differently on each occurrence, a linear alkylene group having up to 10 C atoms, a branched or cyclic alkylene or alkylidene group having 3 to 10 C atoms, a divalent aromatic group having 6 to 25 C atoms, —O—, —S—, —N(R3)—, —P(═O)R3—, or a single bond. ### Claim 13 (depends on 1) The organic electroluminescent device of claim 1, wherein the compounds of formula (2) and/or formula (3) are pure hydrocarbon compounds. ### Claim 14 (depends on 1) The organic electroluminescent device of claim 1, further comprising at least one optionally doped additional layer selected from the group consisting of hole-injection layers, hole-transport layers, electron-transport layers, electron-injection layers, and combinations thereof, and wherein said organic electroluminescent device optionally comprises a plurality of emitting layers making it capable of emitting white light. ### Claim 15 (depends on 1) A process for producing the organic electroluminescent device of claim 1, wherein at least one compound of formula (1) is applied together with at least one compound of formula (2) and/or formula (3) by a sublimation method or from solution, for example by a printing process. ### Claim 16 (depends on 15) The process of claim 15, wherein at least one compound of formula (1) is applied together with at least one compound of formula (2) and/or formula (3) by a printing process. ### Claim 17 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. ### Claim 18 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. ### Claim 19 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. ### Claim 20 (depends on 1) The organic electroluminescent device of claim 1, 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 10.0% 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 90.0 to 99.0% by weight. ### Claim 21 (depends on 18) The organic electroluminescent device of claim 18, 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 10.0% 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 90.0 to 99.0% by weight. ### Claim 22 (depends on 1) The organic electroluminescent device of claim 1, wherein said at least one compound of formula (1) is present in said mixture as a dopant in an amount of from 2.0 to 5.0% 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 95.0 to 98.0% by weight. ### Claim 23 (depends on 1) The organic electroluminescent device of claim 1, wherein said at least one compound of formula (1) is present in said mixture as a dopant in an amount of from 2.0 to 5.0% 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 95.0 to 98.0% by weight.