# US 12,595,256 B2 · Composition for organic electronic devices

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- Number: US 12,595,256 B2
- Document ID: US12595256B2
- Status: Granted
- Kind: B2
- Application number: 15/733,850
- Filed: 2019-05-28
- Published: 2022-10-20
- Granted: 2026-04-07
- Earliest claimed: 2018-05-30
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Amir Parham; Jonas Kroeber; Jens Engelhart; Anja Jatsch; Christian Eickhoff; Christian Ehrenreich
- Web page: https://patentgrep.com/patent/US12595256B2

## CPC

- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 493/00: Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C09K 11/06: containing organic luminescent materials
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/623: {containing five rings, e.g. pentacene}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- 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}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1029: containing one nitrogen atom as the 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 50/16: Electron transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 50/18: Carrier blocking layers
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- Y02E 10/549: Organic PV cells
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The invention relates to a composition comprising an electron-transporting host and a hole-transporting host, to the use thereof in electronic devices and to electronic devices containing said composition. The electron-transporting host is most preferably selected from the class of triazine-dibenzofurane-fluorenyl systems or from the class of triazine-dibenzothiophene-fluorenyl systems. The hole-transporting host is preferably selected from the class of biscarbazoles.

## Claims

### Claim 1

An emitting layer, an electron transport layer, an electron injection layer or a hole blocker layer comprising a composition comprising at least one compound of the formula (1k) and at least one compound of the formula (2e)
where the symbols and indices used are as follows:
Y is selected from O and S;
RB is Ar3;
Ar1, Ar2 at each instance are each independently are selected from Ar-1 to Ar-12
Ar3 is an aromatic ring system having 6 to 40 aromatic ring atoms selected from Ar-2 to Ar-7
R is the same or different at each instance and is selected from the group consisting of D, F, CN and an aryl group having 6 to 10 carbon atoms;
R1 is the same or different at each instance and is selected from the group consisting of D, F, an alkyl group having 1 to 40 carbon atoms or an aromatic or heteroaromatic ring system which has 5 to 40 aromatic ring atoms;
R3 is the same or different at each instance and is selected from the group consisting of H or D;
R4 is D;
R5 is the same or different at each instance and is D or phenyl; and
Aryl is an aryl group containing 6 to 40 carbon atoms
n and m at each instance are independently 0, 1, 2 or 3,
o at each instance is independently 0, 1, 2, 3, 4, 5, 6 or 7;
q at each instance is independently 0, 1, 2 or 3;
p at each instance is independently 0, 1, 2, 3 or 4
r and s are each independently 0, 1, 2, 3 or 4.

### Claim 2 (depends on 1)

The emitting layer, the electron transport layer, the electron injection layer or the hole blocker layer as claimed in claim 1, wherein Y in formula (1k) is O.

### Claim 3 (depends on 1)

The emitting layer, the electron transport layer, the electron injection layer or the hole blocker layer as claimed in claim 1, wherein the composition further comprises at least one compound selected from the group consisting of hole injection materials, hole transport materials, hole blocker materials, wide band gap materials, fluorescent emitters, phosphorescent emitters, host materials, matrix materials, electron blocker materials, electron transport materials and electron injection materials, n-dopants and p-dopants.

### Claim 4 (depends on 1)

An organic electronic device comprising the emitting layer, the electron transport layer, the electron injection layer or the hole blocker layer as claimed in claim 1.

### Claim 5 (depends on 4)

The device as claimed in claim 4, wherein the organic electronic device is selected from the group of organic integrated circuits (OICs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors.

### Claim 6 (depends on 5)

The device as claimed in claim 5, wherein the device is an electroluminescent device selected from organic light-emitting transistors (OLETs), organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs).

### Claim 7 (depends on 1)

An organic electronic device which comprises the emitting layer, electron transport layer, electron injection layer, or hole blocker layer as claimed in claim 1 together with a phosphorescent emitter.

### Claim 8 (depends on 1)

A process for producing an organic electronic device, which comprises applying at least one emitting layer, electron transport layer, electron injection layer or hole blocker layer as claimed in claim 1 by gas phase deposition or from solution.

### Claim 9 (depends on 1)

The emitting layer, the electron transport layer, the electron injection layer or the hole blocker layer as claimed in claim 1 wherein the compound of formula (1k) is selected from the following compounds:
