# US 2018/0323384 A1 · Platinum (ii) emitters for oled applications

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- Number: US 2018/0323384 A1
- Document ID: US20180323384A1
- Status: Published application
- Kind: A1
- Application number: 16/035,793
- Filed: 2018-07-16
- Published: 2018-11-08
- Earliest claimed: 2014-04-03
- Assignees: Versitech Limited
- Applicants: Versitech Limited
- Inventors: Chi Ming Che; Chi Fai Kui; Chi Chung Kwok
- Web page: https://patentgrep.com/patent/US20180323384A1

## CPC

- H10K 85/346: {comprising platinum}
- C07F 15/0086: {Platinum compounds}
- C09K 11/06: containing organic luminescent materials
- 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 2101/10: Triplet emission
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Described herein are novel platinum(II) emitters. These materials show high emission quantum efficiency, a low self-quenching constant and are stable in thermal deposition process. Organic light-emitting diodes (OLEDs) fabricated from these materials can have pure green emission, high efficiency and low efficiency roll-off. The OLEDs can have a chemical structure of:

## Claims

### Claim 1

An organic light-emitting diode (OLED) emitter having a chemical structure of Structure I:
wherein R1-R13 are independently hydrogen, halogen, hydroxyl, an unsubstituted alkyl, a substituted alkyl, cycloalkyl, an unsubstituted aryl, a substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, acylamino, aralkyl, cyano, carboxyl, thio, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or an alkoxycarbonyl group, each pair of adjacent R groups of R1-R13 can independently join together to form a 5-8 member ring(s);
wherein B is a hydrocarbon group containing 1 to 24 carbon atoms or a substituted aryl group; and
wherein
is a spiro-linkage.

### Claim 2 (depends on 1)

The OLED emitter in claim 1, wherein the spiro-linkage is:
wherein R14-R21 are independently hydrogen, halogen, hydroxyl, an unsubstituted alkyl, a substituted alkyl, cycloalkyl, an unsubstituted aryl, a substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, acylamino, aralkyl, cyano, carboxyl, thio, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or an alkoxycarbonyl group, each pair of adjacent R groups of R14-R21 can independently form 5-8 member ring(s) with 2 or 4 carbon atoms in the phenyl ring(s).

### Claim 3 (depends on 1)

The OLED emitter in claim 1, wherein the spiro-linkage is:
wherein X is selected from C, N, O, S, P or Si; R14-R21 are independently hydrogen, halogen, hydroxy, an unsubstituted alkyl, a substituted alkyl, cycloalkyl, an unsubstituted aryl, a substituted aryl, acyl, alkoxy, acyloxy, amino, nitro, acylamino, aralkyl, cyano, carboxyl, thio, styryl, aminocarbonyl, carbamoyl, aryloxycarbonyl, phenoxycarbonyl, or an alkoxycarbonyl group, each pair of adjacent R groups of R14-R21 can independently form 5-8 member ring(s) with 2 or 4 carbon atoms in the phenyl ring(s).

### Claim 4 (depends on 1)

The OLED emitter in claim 1, wherein the spiro-linkage comprises a substituted aryl group.

### Claim 5 (depends on 1)

The OLED emitter in claim 1, wherein the spiro-linkage comprises at least one benzyl group.

### Claim 6 (depends on 1)

The OLED emitter in claim 1, wherein each R1-R13 is independently hydrogen, halogen, hydroxyl, an unsubstituted alkyl containing from 1 to 10 carbon atoms, a substituted alkyl containing from 1 to 20 carbon atoms, cycloalkyl containing from 4 to 20 carbon atoms, an unsubstituted aryl containing from 6 to 20 carbon atoms, a substituted aryl containing from 6 to 20 carbon atoms, acyl containing from 1 to 20 carbon atoms, alkoxy containing from 1 to 20 carbon atoms, acyloxy containing from 1 to 20 carbon atoms, amino, nitro, acylamino containing from 1 to 20 carbon atoms, aralkyl containing from 1 to 20 carbon atoms, cyano, carboxyl containing from 1 to 20 carbon atoms, thiol, styryl, aminocarbonyl containing from 1 to 20 carbon atoms, carbamoyl containing from 1 to 20 carbon atoms, aryloxycarbonyl containing from 1 to 20 carbon atoms, phenoxycarbonyl containing from 1 to 20 carbon atoms, or an alkoxycarbonyl group containing from 1 to 20 carbon atoms.

### Claim 7 (depends on 1)

The OLED emitter in claim 1, wherein B is:

### Claim 8 (depends on 1)

The OLED emitter in claim 1 having a green emission in dilute solution with emission λmax<520 nm.

### Claim 9 (depends on 1)

The OLED emitter in claim 1 having a short emission lifetime of less than 6 μs.

### Claim 10 (depends on 1)

The OLED emitter in claim 1 having a self-quenching constant in the order of below 10−7 dm3 mol−1 s−1.

### Claim 11 (depends on 1)

A light-emitting device comprising at least one OLED emitter of claim 1 as an emitting material.

### Claim 12 (depends on 11)

The light-emitting device of claim 11, wherein the device is an organic light-emitting diode (OLED).

### Claim 13 (depends on 11)

The light-emitting device of claim 11, wherein the device is fabricated by vacuum deposition.

### Claim 14 (depends on 11)

The light-emitting device of claim 11, wherein the device is fabricated by solution processes.

### Claim 15 (depends on 11)

The light-emitting device of claim 11, wherein the device contains one emissive layer.

### Claim 16 (depends on 11)

The light-emitting device of claim 11, wherein the device contains more than one emissive layer.

### Claim 17 (depends on 11)

The light-emitting device of claim 11, wherein the efficiency roll-off at 1000 cd/m−2 is less than 10%.

### Claim 18 (depends on 11)

The light-emitting device of claim 11, wherein the doping concentration of the emitter is from 2-30 weight % without changing the emitting color (change of CIEx less than 0.03 and or change of CIEy less than 0.02).