# US 10,374,170 B2 · Substituted oxepines

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- Number: US 10,374,170 B2
- Document ID: US10374170B2
- Status: Granted
- Kind: B2
- Application number: 15/101,219
- Filed: 2014-11-18
- Published: 2016-10-20
- Granted: 2019-08-06
- Earliest claimed: 2013-12-06
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Amir Hossain Parham; Arne Buesing; Philipp Stoessel; Anja Gerhard; Christof Pflumm; Thomas Eberle; Anja Jatsch; Jonas Valentin Kroeber; Lars Dobelmann-Mara
- Web page: https://patentgrep.com/patent/US10374170B2

## CPC

- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- A61N 5/0616: {Skin treatment other than tanning}
- C07D 313/06: condensed with carbocyclic rings or ring systems
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 405/10: linked by a carbon chain containing aromatic rings
- C07D 405/14: containing three or more hetero rings
- C07D 407/04: directly linked by a ring-member-to-ring-member bond
- C07D 407/10: linked by a carbon chain containing aromatic rings
- C07D 407/12: linked by a chain containing hetero atoms as chain links
- C07D 407/14: containing three or more hetero rings
- C07D 487/04: Ortho-condensed systems
- C07D 491/044: with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/621: {Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide}
- 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 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- 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 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- A61N 5/067: using laser light
- A61N 2005/0653: {Organic light emitting diodes}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/16: Electron transporting layers
- H10K 50/165: comprising dopants
- H10K 71/10: Deposition of organic active material
- H10K 71/12: using liquid deposition, e.g. spin coating
- H10K 85/624: {containing six or more rings}
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- A61N: ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY (measurement of bioelectric currents A61B; surgical instruments, devices or methods for transferring non-mechanical forms of energy to or from the body A61B18/00; anaesthetic apparatus in general A61M; incandescent lamps H01K; infrared radiators for heating H05B)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

The invention relates to materials, to electroluminescence devices comprising said materials and to the use thereof.

## Claims

### Claim 1

A compound of the formula (4a) or (6a)
V is either O or S,
X is the same or different at each instance and is N or CR1,
R1 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R2)2, CN, NO2, Si(R2)3, B(OR2)2, C(═O)R2, P(═O)(R2)2, S(═O)R2, S(═O)2R2, OSO2R2, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R2 radicals, where one or more nonadjacent CH2 groups is optionally replaced by R2C═CR2, C≡C, Si(R2)2, Ge(R2)2, Sn(R2)2, C═O, C═S, C═Se, C═NR2, P(═O)(R2), SO, SO2, NR2, O, S or CONR2 and where one or more hydrogen atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted in each case by one or more R2 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R2 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and is optionally substituted by one or more R2 radicals, or a combination of two or more of these groups or a crosslinkable Q group; at the same time, two or more adjacent R1 radicals together may form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system which is optionally substituted by one or more R2 radicals;
R2 is the same or different at each instance and is H, D, F, Cl, Br, I, N(R3)2, CN, NO2, Si(R3)3, B(OR3)2, C(═O)R3, P(═O)(R3)2, S(═O)R3, S(═O)2R3, OSO2R3, a straight-chain alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a straight-chain alkenyl or alkynyl group having 2 to 40 carbon atoms or a branched or cyclic alkyl, alkenyl, alkynyl, alkoxy, alkylalkoxy or thioalkoxy group having 3 to 40 carbon atoms, each of which is optionally substituted by one or more R3 radicals, where one or more nonadjacent 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, P(═O)(R3), SO, SO2, NR3, O, S or CONR3 and where one or more hydrogen atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms and is optionally substituted in each case by one or more R3 radicals, or an aryloxy, arylalkoxy or heteroaryloxy group which has 5 to 60 aromatic ring atoms and is optionally substituted by one or more R3 radicals, or a diarylamino group, diheteroarylamino group or arylheteroarylamino group which has 10 to 40 aromatic ring atoms and is optionally substituted by one or more R3 radicals, or a combination of two or more of these groups; at the same time, two or more adjacent R2 radicals together may form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system;
R3 is the same or different at each instance and is H, D, F or an aliphatic, aromatic and/or heteroaromatic hydrocarbyl radical having 1 to 40 carbon atoms, in which one or more hydrogen atoms may also be replaced by F; at the same time, two or more R3 substituents together may also form a mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system;
and with the proviso that at least one of the R1 radicals is not H.

### Claim 2 (depends on 1)

An electronic device comprising at least one compound as claimed in claim 1.

### Claim 3 (depends on 2)

The electronic device as claimed in claim 2, wherein is selected from organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors, organic photoreceptors.

### Claim 4 (depends on 3)

The electronic device as claimed in claim 3, wherein the device is an organic electroluminescent device also selected from the group consisting of organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).

### Claim 5 (depends on 2)

A process for producing the electronic device as claimed in claim 2, wherein at least one organic layer is applied by gas phase deposition or from solution.

### Claim 6 (depends on 2)

A process for phototherapy of the skin which comprises treating the skin with the device as claimed in claim 2.

### Claim 7 (depends on 2)

A process for the reduction or prevention of skin ageing, skin wrinkles, crows' feet, acne, comedones and cellulite which comprises treating the skin with the device according to claim 2.

### Claim 8 (depends on 2)

A display or for lighting which comprises the device as claimed in claim 2.

### Claim 9 (depends on 1)

A composition comprising at least one compound as claimed in claim 1 and at least one additional compound selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron transport materials, electron injection materials, hole conductor materials, hole injection materials, electron blocker materials, hole blocker materials, n-dopants and p-dopants.

### Claim 10 (depends on 9)

The composition as claimed in claim 9, wherein the additional compound is a phosphorescent emitter.

### Claim 11 (depends on 9)

The composition as claimed in claim 9, wherein the additional compound is a host or matrix material.

### Claim 12 (depends on 9)

The composition as claimed in claim 9, wherein the additional compound has a band gap of 2.5 eV or more.

### Claim 13 (depends on 1)

The compound as claimed in claim 1, wherein the compound has the following formula (4a):

### Claim 14 (depends on 1)

The compound as claimed in claim 1, wherein the compound has the following formula (10a):

### Claim 15 (depends on 1)

The compound as claimed in claim 1, wherein the compound has the following formula (6a):

### Claim 16 (depends on 1)

The compound as claimed in claim 1, wherein the compound has the following formula (17):

### Claim 17 (depends on 1)

The compound as claimed in claim 1, wherein the compound has the following formula (18):

### Claim 18 (depends on 1)

A process for preparing the compound as claimed in claim 1 with the aid of Suzuki coupling, Buchwald or Ullmann coupling.

### Claim 19 (depends on 1)

A formulation comprising at least one compound as claimed in claim 1 and at least one solvent.

### Claim 20 (depends on 1)

The compound as claimed in claim 1, wherein V is O.

### Claim 21 (depends on 1)

The compound as claimed in claim 1, wherein the compound is of the Formula (10d)

### Claim 22

A compound of the following formula (A-1)-(A-69), (A-50a)-(A-69a), (A-70)-(A293) and (INV-5)-(INV-29):