# US 2014/0151646 A1 · Compounds for triplet-triplet annihilation upconversion

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- Number: US 2014/0151646 A1
- Document ID: US20140151646A1
- Status: Published application
- Kind: A1
- Application number: 13/693,122
- Filed: 2012-12-04
- Published: 2014-06-05
- Earliest claimed: 2012-12-04
- Assignees: Universal Display Corporation
- Inventors: Chuanjun XIA
- Web page: https://patentgrep.com/patent/US20140151646A1

## CPC

- C09K 11/06: containing organic luminescent materials
- C07F 15/0033: {Iridium compounds}
- C07F 15/0066: {without a metal-carbon linkage}
- C07F 15/0093: {without a metal-carbon linkage}
- H10K 85/341: {Transition metal complexes, e.g. Ru(II)polypyridine complexes (H10K85/331 takes precedence)}
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- H10K 85/791: {Starburst compounds}
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/125: specially adapted for multicolour light emission, e.g. for emitting white light
- H10K 59/38: comprising colour filters or colour changing media [CCM]
- Y02E 10/549: Organic PV cells
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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

Novel compounds, and in particular, a dendritic system for improved triple-triplet annihilation upconversion (TTA-UC) are provided. The core of the dendrimer compound includes a metal complex, and on the peripheral, multiple acceptor moieties are covalently linked to the core through a spacer. Consequently, a high efficiency TTA-UC system in both solution and solid state is provided, with particularly high efficiency in the solid state. Additionally, organic light emitting devices (OLEDs) comprising a layer including these novel compounds are provided.

## Claims

### Claim 1

A compound for triplet-triplet annihilation upconversion comprising:
a metal complex sensitizer core;
a first acceptor group; and
a first spacer group between the metal complex core and the first acceptor group, wherein the first acceptor group has a first triplet energy lower than a first triplet energy of the metal complex sensitizer core.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the first spacer group substantially surrounds the metal complex sensitizer core.

### Claim 3 (depends on 1)

The compound of claim 1, further comprising a second spacer group, wherein the second spacer group substantially surrounds the first acceptor group.

### Claim 4 (depends on 3)

The compound of claim 3, further comprising a second acceptor group.

### Claim 5 (depends on 4)

The compound of claim 4, wherein the second acceptor group substantially surrounds the second spacer group.

### Claim 6 (depends on 1)

The compound of claim 1, further comprising a second acceptor group.

### Claim 7 (depends on 1)

The compound of claim 1, further comprising a second spacer group.

### Claim 8 (depends on 1)

A device comprising a layer, the layer comprising a compound of claim 1.

### Claim 9 (depends on 8)

The device of claim 8, wherein the device comprises an OLED.

### Claim 10 (depends on 9)

The device of claim 9, further comprising a thin film encapsulation layer disposed over or under the OLED.

### Claim 11 (depends on 1)

A consumer product comprising the compound of claim 1.

### Claim 12

A compound for triplet-triplet annihilation upconversion, wherein the compound has the following general structure:
wherein A is a metal complex;
wherein L1 to Lx is a spacer group;
wherein B1 to Bx is an acceptor group B;
wherein m1 is greater than 0;
wherein mx is equal to or greater than 0,
wherein n is greater than 0, and
wherein the acceptor group B has a first triplet energy lower than a first triplet energy of the metal complex A.

### Claim 13 (depends on 12)

The compound of claim 12, wherein m1 is in the range of 1 to 20.

### Claim 14 (depends on 12)

The compound of claim 12, wherein mx is in the range of 0 to 20.

### Claim 15 (depends on 12)

The compound of claim 12, wherein n is in the range of 1 to 20.

### Claim 16 (depends on 12)

The compound of claim 12, wherein the metal complex is selected from the group consisting of: an iridium complex, an osmium complex, a platinum complex, a palladium complex, a rhenium complex, a ruthenium complex, and a gold complex.

### Claim 17 (depends on 12)

The compound of claim 12, wherein the acceptor group B is a fused aromatic group.

### Claim 18 (depends on 12)

The compound of claim 12, wherein the acceptor group B is selected from the group consisting of: naphthalene, anthracene, tetracene, pyrene, chrysene, and perylene.

### Claim 19 (depends on 12)

The compound of claim 12, wherein the ratio of the acceptor group B to the metal complex A is at least 4.

### Claim 20 (depends on 12)

The compound of claim 12, wherein the spacer group L is selected from the group consisting of: alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, ester, and combinations thereof.

### Claim 21 (depends on 12)

A device comprising a layer, the layer comprising a compound of claim 12.

### Claim 22 (depends on 21)

The device of claim 21, wherein the device comprises a light emitting diode.

### Claim 23 (depends on 21)

The device of claim 21, wherein the device comprises an OLED.

### Claim 24 (depends on 23)

The device of claim 23, further comprising a thin film encapsulation layer disposed over or under the OLED.

### Claim 25 (depends on 12)

A consumer product comprising the compound of claim 12.

### Claim 26 (depends on 12)

A photovoltaic device comprising the compound of claim 12.

### Claim 27 (depends on 12)

A device, comprising:
an organic light emitting device comprising an emissive material having an emissive spectrum; and
an up-conversion layer disposed adjacent to the organic light emitting device such that light emitted by the organic light emitting device is incident on the up-conversion layer, the up-conversion layer comprising the compound of claim 12.

### Claim 28

A compound selected from the group consisting of:
