# US 2008/0303003 A1 · Novel Materials for Organic Electroluminescent Devices

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- Number: US 2008/0303003 A1
- Document ID: US20080303003A1
- Status: Published application
- Kind: A1
- Application number: 12/096,464
- Filed: 2006-11-17
- Published: 2008-12-11
- Earliest claimed: 2005-12-08
- Assignees: Merck Patent GmbH
- Inventors: Holger Heil; Philipp Stoessel; Amir Parham; Horst Vestweber
- Web page: https://patentgrep.com/patent/US20080303003A1

## CPC

- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C07F 7/0805: {comprising only Si, C or H atoms}
- C07F 7/081: {comprising at least one atom selected from the elements N, O, halogen, S, Se or Te}
- C07F 7/0812: {comprising a heterocyclic ring}
- C07F 7/0814: {said ring is substituted at a C ring atom by Si}
- 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 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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

## Abstract

The present invention relates to anthracene derivatives, to the use thereof in organic electroluminescent devices, and to organic electroluminescent devices comprising these compounds.

## Claims

### Claim at position 1

1-16. (canceled)

### Claim 17

A silyl-substituted compound of formula (1)
wherein
Ar is a 1-naphthyl group or a 9-anthryl group, each optionally substituted by one or more radicals R1 and/or one or more radicals N(Ar1)2, wherein one or two carbon atoms of said 1-naphthyl group or said 9-anthryl group is optionally replaced by N, and wherein the two radicals Ar1 are optionally connected to one another by a single bond or an O, S, N(R1), or C(R1)2 group;
R is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms and optionally substituted by one or more radicals R1 or an N(Ar1)2 group, where the two radicals Ar1 are optionally connected to one another by a single bond or an O, S, N(R1), or C(R1)2 group;
Ar1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms and optionally substituted by one or more radicals R1;
Y is, identically or differently on each occurrence, a divalent group containing up to 40 C atoms, —O—, —S—, —NR1—, —P(═O)R1—, or a single bond;
R1 is, identically or differently on each occurrence, Si(R2)3; F; Cl; Br; I; CN; N(R3)2; NO2; a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 C atoms and optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups are 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 are 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 and optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups are 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 are optionally replaced by F, Cl, Br, I, CN, or NO2; an aryl or heteroaryl group having 5 to 24 aromatic ring atoms and optionally substituted by one or more radicals R3; or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms and 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 R1 optionally define a mono- or polycyclic, aliphatic ring system with one another;
R2 is, identically or differently on each occurrence, a straight-chain alkyl group having up to 40 C atoms and optionally substituted by an aryl or heteroaryl group having 5 to 24 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; wherein one or more non-adjacent CH2 groups which are not bonded directly to silicon are 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 group having 3 to 40 C atoms optionally substituted by an aryl or heteroaryl group having 5 to 24 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, wherein one or more non-adjacent CH2 groups which are not bonded directly to silicon are 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; and wherein two or more substituents R2 optionally define a mono- or polycyclic ring system with one another;
R3 is, identically or differently on each occurrence, H or a hydrocarbon radical having up to 20 C atoms, which may be aliphatic or aromatic or a combination of aliphatic and aromatic and is optionally substituted by F; and wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
n is, identically or differently on each occurrence, 0, 1, 2, 3, or 4; and
m is 0, 1, 2, 3, 4, or 5;
wherein at least one radical R1 which represents an Si(R2)3 group is present.

### Claim 18 (depends on 17)

The silyl-substituted compound of claim 17, wherein said compound is of formula (1a), (1b), (1c), or (1d):
wherein
the two radicals Ar1 are optionally connected to one another by a single bond or an O, S, N(R1), or C(R1)2 group;
o is 0, 1, 2, or 3;
p is 0 or 1; and
q is 0, 1 or 2.

### Claim 19 (depends on 18)

The silyl-substituted compound of claim 18, wherein p is 1.

### Claim 20 (depends on 17)

The silyl-substituted compound of claim 17, wherein R is an aromatic or heteroaromatic ring system having 6 to 24 aromatic ring atoms and optionally substituted by one or more radicals R1; or is a group of formula (2a) or (2b)
wherein
X is a single bond, O, S, N(R1), or C(R1)2;
Ar1 is, identically or differently on each occurrence, an aryl or heteroaryl group having 5 to 20 aromatic ring atoms and optionally substituted by one or more radicals R1.

### Claim 21 (depends on 20)

The silyl-substituted compound of claim 20, wherein said aryl or heteroaryl group has 6 to 14 aromatic ring atoms and is optionally substituted by one or more radicals R1

### Claim 22 (depends on 21)

The silyl-substituted compound of claim 21, wherein said aryl or heteroaryl group is phenyl, 1-naphthyl, or 2-naphthyl, each of which is optionally substituted by one or more radicals R1.

### Claim 23 (depends on 17)

The silyl-substituted compound of claim 17, wherein R is a condensed aryl or heteroaryl group having 10 to 16 aromatic ring atoms or an aromatic, optionally bridged biaryl group, each of which is optionally substituted by one or more radicals R1.

### Claim 24 (depends on 23)

The silyl-substituted compound of claim 23, wherein R is a 1-naphthyl, 2-naphthyl, 9-anthryl, 2-phenanthrenyl, 9-phenanthrenyl, quinolinyl, isoquinolinyl, orthobiphenyl, meta-biphenyl, para-biphenyl, 2-fluorenyl, or 2-spirobifluorenyl group, each of which is optionally substituted by one or more radicals R1.

### Claim 25 (depends on 17)

The silyl-substituted compound of claim 17, wherein R1 is, identically or differently on each occurrence, Si(R2)3; F; a straight-chain alkyl or alkoxy group having up to 6 C atoms wherein one or more CH2 groups is optionally replaced by —R3C═CR3—, Si(R3)2, —O—, —S—, or —N(R3)— and wherein one or more H atoms is optionally replaced by F; a branched or cyclic alkyl or alkoxy group having 3 to 10 C atoms, wherein one or more CH2 groups is optionally replaced by —R3C═CR3—, Si(R3)2, —O—, —S—, or —N(R3)— and wherein one or more H atoms is optionally replaced by F; or an aryl or heteroaryl group having 5 to 14 aromatic ring atoms and optionally substituted by one or more radicals R3; or a combination of two or three of these systems; and wherein two or more radicals R1 optionally define a mono- or polycyclic, aliphatic ring system with one another.

### Claim 26 (depends on 17)

The silyl-substituted compound of claim 17, wherein Y 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, C═O, —O—, —S—, —N(R1)—, —P(═O)R1—, or a single bond.

### Claim 27 (depends on 17)

The silyl-substituted compound of claim 17, wherein it contains one, two, three, or four groups of formula Si(R2)3.

### Claim 28 (depends on 17)

The silyl-substituted compound of claim 17, wherein at least one Si(R2)3 group is bonded to the central anthracene unit, and/or in that at least one group of the formula Si(R2)3 is bonded to the Ar group, and/or in that at least one group of the formula Si(R2)3 is bonded to the R group.

### Claim 29 (depends on 28)

The silyl-substituted compound of claim 28, wherein at least one Si(R2)3 group is bonded to the central anthracene unit in the 2-position and/or in the 6-position, and/or in that at least one group of the formula Si(R2)3 is bonded to the Ar group in the 4-position if Ar is a naphthyl or in the 10-position if Ar is anthryl, and/or in that at least one group of the formula Si(R2)3 is bonded to the R group.

### Claim 30 (depends on 17)

The silyl-substituted compound of claim 17, wherein R2 of Si(R2)3 is selected from the group consisting of straight-chain alkyl groups having up to 10 C atoms, wherein one or more non-adjacent CH2 groups which are not bonded directly to the silicon are optionally replaced by O and wherein one or more H atoms is optionally replaced by F, and branched or cyclic alkyl groups having 3 to 10 C atoms, wherein one or more non-adjacent CH2 groups which are not bonded directly to the silicon are optionally replaced by O and wherein one or more H atoms is optionally replaced by F; and wherein two or more substituents R2 optionally define a mono- or polycyclic ring system with one another.

### Claim 31 (depends on 17)

A process for preparing a compound of claim 17 which carry one or more Si(R2)3 groups on the Ar or R group, comprising coupling a functionalised Ar or R group which is substituted by one or more Si(R2)3 groups to a corresponding anthracene derivative.

### Claim 32 (depends on 17)

An organic electronic device comprising at least one compound of claim 17.

### Claim 33 (depends on 32)

The organic electronic device of claim 32, wherein said device is selected from the group consisting of organic electroluminescent devices, organic field-effect transistors, organic thin-film transistors, organic light-emitting transistors, organic integrated circuits, organic solar cells, organic field-quench devices, organic photoreceptors, light-emitting electrochemical cells, and organic laser diodes.

### Claim 34 (depends on 32)

The organic electronic device of claim 32, wherein said device is a organic electroluminescent device comprising at least one emitting layer, hole-transport layer, hole-injection layer, hole-blocking layer, and/or electron-transport layer, wherein at least one of said layers comprises at least one silyl-substituted compound of formula (1)
wherein
Ar is a 1-naphthyl group or a 9-anthryl group, each optionally substituted by one or more radicals R1 and/or one or more radicals N(Ar1)2, wherein one or two carbon atoms of said 1-naphthyl group or said 9-anthryl group is optionally replaced by N, and wherein the two radicals Ar1 are optionally connected to one another by a single bond or an O, S, N(R1), or C(R1)2 group;
R is an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms and optionally substituted by one or more radicals R1 or an N(Ar1)2 group, where the two radicals Ar1 are optionally connected to one another by a single bond or an O, S, N(R1), or C(R1)2 group;
Ar1 is, identically or differently on each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms and optionally substituted by one or more radicals R1;
Y is, identically or differently on each occurrence, a divalent group containing up to 40 C atoms, —O—, —S—, —NR1—, —P(═O)R1—, or a single bond;
R1 is, identically or differently on each occurrence, Si(R2)3; F; Cl; Br; I; CN; N(R3)2; NO2; a straight-chain alkyl alkoxy or thioalkoxy group having 1 to 40 C atoms and optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups are 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 are 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 and optionally substituted by one or more radicals R3, wherein one or more non-adjacent CH2 groups are 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 are optionally replaced by F, Cl, Br, I, CN, or NO2; an aryl or heteroaryl group having 5 to 24 aromatic ring atoms and optionally substituted by one or more radicals R3; or an aryloxy or heteroaryloxy group having 5 to 24 aromatic ring atoms and 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 R1 optionally define a mono- or polycyclic, aliphatic ring system with one another;
R2 is, identically or differently on each occurrence, a straight-chain alkyl group having up to 40 C atoms and optionally substituted by an aryl or heteroaryl group having 5 to 24 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; wherein one or more non-adjacent CH2 groups which are not bonded directly to silicon are 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 group having 3 to 40 C atoms optionally substituted by an aryl or heteroaryl group having 5 to 24 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, wherein one or more non-adjacent CH2 groups which are not bonded directly to silicon are 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; and wherein two or more substituents R2 optionally define a mono- or polycyclic ring system with one another;
R3 is, identically or differently on each occurrence, H or a hydrocarbon radical having up to 20 C atoms, which may be aliphatic or aromatic or a combination of aliphatic and aromatic and is optionally substituted by F; and wherein two or more radicals R3 optionally define a mono- or polycyclic, aliphatic or aromatic ring system with one another;
n is, identically or differently on each occurrence, 0, 1, 2, 3, or 4; and
m is 0, 1, 2, 3, 4, or 5;
wherein at least one radical R1 which represents an Si(R2)3 group is present.

### Claim 35 (depends on 34)

The organic electroluminescent device of claim 34, wherein said at least one silyl-substituted compound of formula (1) is employed as host material for fluorescent emitters and/or as electron-transport material and/or as hole-blocking material when R is an aromatic or heteroaromatic ring system.

### Claim 36 (depends on 34)

The organic electroluminescent device of claim 34, wherein said at least one silyl-substituted compound of formula (1) is employed as emitting compound and/or as hole-transport material when R is N(Ar1)2.