# US 11,440,925 B2 · Compounds for electronic devices

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- Number: US 11,440,925 B2
- Document ID: US11440925B2
- Status: Granted
- Kind: B2
- Application number: 16/347,847
- Filed: 2017-11-06
- Published: 2019-08-29
- Granted: 2022-09-13
- Earliest claimed: 2016-11-08
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Teresa Mujica-Fernaud; Rémi Anémian; Hyeon-Hui Kang; Il Jung; Jun-Ho Kim
- Web page: https://patentgrep.com/patent/US11440925B2

## CPC

- C07F 7/0816: {said ring comprising Si as a ring atom}
- H10K 85/40: Organosilicon compounds, e.g. TIPS pentacene
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/155: comprising dopants
- H10K 85/622: {containing four rings, e.g. pyrene}
- 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}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- 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}
- Y02E 10/549: Organic PV cells
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present application concerns silafluorene derivatives according to a specific formula. The silafluorene derivatives can be employed in electronic devices. Furthermore, the present application concerns methods for preparation of the silafluorene derivatives, and electronic devices comprising the silafluorene derivatives.

## Claims

### Claim 1

A compound of a formula (I)
where the following applies to the variable groups:
Z is, identically or differently on each occurrence, selected from CRA;
X is, identically or differently on each occurrence, selected from CR2;
R1 is selected, identically or differently at each occurrence, from H, D, F, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R1 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R4, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R4C═CR4—, —C═C—, Si(R4)2, CO═O, C═NR4, —C(═O)O—, —C(═O)NR4—, NR4, P(═O)(R4), —O—, —S—, SO or SO2;
RA and R2 are selected, identically or differently at each occurrence, from H, D, F, C(═O)R4, CN, Si(R4)3, P(═O)(R4)2, OR4, S(═O)R4, S(═O)2R4, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms and not comprising any heteroatoms as aromatic ring atoms, where two or more radicals RA and/or R2 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic systems may in each case be substituted by one or more radicals R4, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R4C═CR4—, Si(R4)2, C═O, C═NR4, —C(═O)O—, —C(═O)NR4—, NR4, P(═O)(R4), —O—, —S—, SO or SO2;
R4 is selected, identically or differently at each occurrence, from H, D, F, C(═O)R5, CN, Si(R5)3, N(R5)2, P(═O)(R5)2, OR5, S(═O)R5, S(═O)2R5, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R4 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R5, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R5C═CR5—, —C═C—, Si(R5)2, CO═O, C═NR5, —C(═O)O—, —C(═O)NR5—, NR5, P(═O)(R5), —O—, —S—, SO or SO2;
R5 is selected, identically or differently at each occurrence, from H, D, F, CN, alkyl groups having 1 to 20 C atoms, aromatic ring systems having 6 to 40 C atoms, or heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R5 may be connected to each other to form a ring; and where the said alkyl groups, aromatic ring systems and heteroaromatic ring systems may be substituted by F and CN;
provided that
a) at least one radical RA is replaced by a group according to formula (A)
where the group according to formula (A) is attached via the free bond on the left of the structure of formula (A), and where the variables in formula (A) are defined as follows:
Ar1 is selected, identically or differently on each occurrence, from phenyl, biphenyl, branched terphenyl, non-branched terphenyl, branched quaterphenyl, non-branched quaterphenyl, fluorenyl, naphthyl, anthracenyl, pyridyl, quinolinyl, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, fluorenyl-phenylenyl, dibenzofuranyl-phenylenyl, dibenzothiophenyl-phenylenyl, phenanthrenyl and triphenylyl, each of which may be substituted by one or more radicals R3;
L1 is selected, identically or differently on each occurrence, from aromatic ring systems having 6 to 30 aromatic ring atoms and from heteroaromatic ring systems having 5 to 30 aromatic ring atoms, each of which may be substituted by one or more radicals R3;
R3 is selected, identically or differently at each occurrence, from H, D, F, C(═O)R4, CN, Si(R4)3, N(R4)2, P(═O)(R4)2, S(═O)R4, S(═O)2R4, straight-chain alkyl or alkoxy groups having 1 to 20 C atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 C atoms, alkenyl or alkynyl groups having 2 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R3 may be connected to each other to form a ring; where the said alkyl, alkoxy, alkenyl and alkynyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R4, and where one or more CH2 groups in the said alkyl, alkoxy, alkenyl and alkynyl groups may in each case be replaced by —R4C═CR4—, —C═C—, Si(R4)2, CO═O, C═NR4, —C(═O)O—, —C(═O)NR4—, NR4, P(O)(R4), —O—, —S—, SO or SO2;
n is 0, 1, 2 or 3.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein exactly one radical RA is replaced by a group according to formula (A), as defined in claim 1.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein R1 is on each occurrence, identically or differently, selected from straight-chain alkyl groups having 1 to 10 C atoms, branched or cyclic alkyl groups having 3 to 10 C atoms, aromatic ring systems having 6 to 24 aromatic ring atoms, and heteroaromatic ring systems having 5 to 24 aromatic ring atoms, where the said alkyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R4.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein RA is, identically or differently on each occurrence, selected from H, D, F, CN, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals RA may be connected to each other to form a ring; and where the said alkyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R4.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein R2 is, identically or differently on each occurrence, selected from H, D, F, CN, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R2 may be connected to each other to form a ring; and where the said alkyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R4.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein R3 is selected, identically or differently at each occurrence, from H, D, F, CN, N(R4)2, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R3 may be connected to each other to form a ring; and where the said alkyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R4.

### Claim 7 (depends on 1)

The compound according to claim 1, wherein R4 is selected, identically or differently at each occurrence, from H, D, F, CN, N(R5)2, straight-chain alkyl groups having 1 to 20 C atoms, branched or cyclic alkyl groups having 3 to 20 C atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; where two or more radicals R4 may be connected to each other to form a ring; and where the said alkyl groups and the said aromatic and heteroaromatic ring systems may in each case be substituted by one or more radicals R5.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein n is 0.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein the compound of formula (I) conforms to one of formulae (I-1) to (I-2)
where the variables occurring are defined as in claim 1, and where radicals RA are not replaced by groups according to formula (A), and where hydrogen atoms or substituents R4 of groups R1 are not replaced by groups according to formula (A).

### Claim 10 (depends on 1)

A process for preparation of a compound according claim 1, comprising reacting a mono- or dihalogenated silyl derivative with a halogenated biphenyl group to form the compound according claim 1.

### Claim 11 (depends on 1)

An oligomer, polymer or dendrimer, comprising one or more compounds of formula (I) according to claim 1, where the bond(s) to the polymer, oligomer or dendrimer may be localised at any desired positions in formula (I) substituted by R1, R2 or R3.

### Claim 12 (depends on 1)

A formulation, comprising at least one compound of formula (I) according to claim 1 and at least one solvent.

### Claim 13 (depends on 1)

An electronic device, comprising at least one compound according to claim 1.

### Claim 14 (depends on 13)

The electronic device according to claim 13, wherein the electronic device is an organic electroluminescent device, comprising anode, cathode and at least one emitting layer, where at least one organic layer of the device, which is an emitting layer or a hole-transporting layer, comprises the at least one compound.