# US 10,312,456 B2 · Organic molecules for OLEDs and other optoelectronic devices

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- Number: US 10,312,456 B2
- Document ID: US10312456B2
- Status: Granted
- Kind: B2
- Application number: 14/367,666
- Filed: 2012-12-11
- Published: 2015-06-04
- Granted: 2019-06-04
- Earliest claimed: 2011-12-22
- Assignees: Cynora GmbH
- Applicants: Cynora GmbH
- Inventors: Hartmut Yersin; Alexander Hupfer
- Web page: https://patentgrep.com/patent/US10312456B2

## CPC

- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- C09K 11/06: containing organic luminescent materials
- H10K 50/12: comprising dopants
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- H10K 85/657: {Polycyclic condensed heteroaromatic hydrocarbons}
- C09K 2211/1011: Condensed systems
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/1096: containing other heteroatoms
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/121: {for assisting energy transfer, e.g. sensitization}
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 2101/10: Triplet emission
- 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
- 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 a composition having an organic emitter molecule, which has a ΔE(S1−T1) value between the lowest excited singlet state (S1) and the triplet state thereunder of less than 3000 cm−1 and an atom or molecule for reducing the intersystem crossing time constant of the organic molecule.

## Claims

### Claim 1

A composition comprising:
an organic emitter molecule for emission of light, comprising a ΔE(S1−T1) value between a lowest excited singlet state (S1) and a triplet state (T1) below the lowest excited singlet state of less than 3000 cm−1; and
an optically inert atom or a molecule;
wherein the optically inert atom or molecule interacts with the organic emitter molecule to reduce an intersystem crossing time constant of the organic emitter molecule to less than 300 ms,
wherein the organic emitter molecule is a molecule of formula V:
wherein
at least one of D1 to D8 is hydrogen or represents a donor group, each independently selected from the group consisting of: —O(—), —NH-alkyl group, —N-(alkyl group)2, —NH2, —OH, —O-alkyl group, —NH(CO)alkyl group, —O(CO), -alkyl group, -aryl group, -heterocyclic groups —(CH)═C-(alkyl group)2, -phenoxazinyl, -phenothiazinyl, -carbazolyl, -dihydrophenazinyl, —N(R′)(R″) wherein R′ and R″ are H, alkyl, aryl, halogenated alkyl, halogenated aryl), wherein all aryl and heterocyclic groups can be substituted with alkyl and/or aryl groups, and all alkyl groups can also be substituted with F, Cl, Br and/or I;
wherein adjacent Di, Dj, and Dk from D1 to D8 optionally are conjugated aromatic or heteroaromatic rings, which may have a donor function, wherein i, j and k are each an integer from 1 to 8 and different from each other;
at least one of A1 to A8 is hydrogen or represents an acceptor group, each independently selected the group consisting of -halogen, —(CO)H, —(CO)-alkyl group, —(CO)O-alkyl group, —(CO)OH, —(CO)Cl, —CF3, —BF2, —CN, —S(O)2OH, —S(O)2O-alkyl, —NH3+, —N(alkyl group)3+, —NO2, halogenated alkyl, and —B(R′)(R″) wherein R′ and R″ are H, alkyl, aryl, halogenated alkyl, halogenated aryl;
wherein adjacent Ai, Aj, and Ak from A1 to A8 optionally are conjugated aromatic or heteroaromatic rings, which may have an acceptor function, wherein i, j and k are each an integer from 1 to 8 and different from each other;
at least one donor group and at least one acceptor group are present;
wherein the optically inert atom or molecule is selected from the group consisting of krypton, xenon, bromine-comprising substances, iodine-comprising substances, metal atoms, metal nanoparticles, metal ions, gadolinium-complexes and lead complexes, and
further wherein the organic emitter molecule is embedded into a matrix or cross-linked with a matrix and wherein the matrix comprises at least one covalently bonded additive selected from a bromine atom or an iodine atom.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein the optically inert atom or molecule comprises a spin-orbit coupling constant of greater than 1000 cm−1.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein the ratio between the organic emitter molecule and the optically inert atom or molecule in the composition is in the range of 1:0.1 to 1:10.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein the organic emitter molecule has at a temperature T=300 K, an emission decay time of less than 500 ms and an emission quantum yield of at least 30%.

### Claim 5 (depends on 1)

The composition according to claim 1, wherein the matrix comprises at least one deuterium atom.

### Claim 6 (depends on 1)

The composition according to claim 1, wherein the matrix is a polymer matrix or a polymer cross-linked matrix, and the matrix is covalently linked with the organic emitter molecule.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the matrix comprises one of glucose, trehalose or a combination thereof.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the composition is used in an emitter layer of an optoelectronic device.