# US 10,246,475 B2 · Multidentate dinuclear cyclometallated platinum complexes containing N-(pyrimidin-2-yl)-carbazole and its analogues

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- Number: US 10,246,475 B2
- Document ID: US10246475B2
- Status: Granted
- Kind: B2
- Application number: 15/709,303
- Filed: 2017-09-19
- Published: 2019-01-10
- Granted: 2019-04-02
- Earliest claimed: 2017-07-04
- Assignees: Zhejiang University of Technology; AAC Microtech (Changzhou) Co., Ltd.
- Applicants: Zhejiang University of Technology; AAC Microtech (Changzhou) Co., Ltd.
- Inventors: Guijie Li; Yuanbin She; Xiangdong Zhao; Shaohai Chen
- Web page: https://patentgrep.com/patent/US10246475B2

## CPC

- C07F 15/0086: {Platinum compounds}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 85/346: {comprising platinum}
- H10K 85/361: {Polynuclear complexes, i.e. complexes comprising two or more metal centers}
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1044: containing two nitrogen atoms as heteroatoms
- 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
- Y02E 10/549: Organic PV cells
- 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
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Disclosed herein are multidentate dinuclear cyclometallated platinum complexes. The complexes are suitable as emitting materials or host materials in OLED devices, the materials having one of the following structures:

## Claims

### Claim 1

A compound of Formula I:
wherein each of L1 and L2 is independently a six-membered carbocyclic, heterocyclic, heteroaryl ring;
wherein each of Y1, Y2, Y3 independently comprises N and C;
wherein V1, V2, V3, V4, V5, V6, V7 and V8 are coordinated with M1 or M2 and each independently comprises N and C; and at least two of V1, V2, V3 and V4 are N, at least two of V5, V6, V7 and V8 are N;
wherein each of A1 and A2 is independently selected from the group consisting O, S, CH2, CD2, CRaRb, C═O, SiRaRb, GeH2, GeRaRb, NH, NRc, PH, PRc, RcP═O, AsRc, RcAs═O, S═O, SO2, Se, Se═O, SeO2, BH, BRc, RcBi═O, BiH, or BiRc;
wherein each of X, X1 and X2 is independently selected from the group consisting N, B, CH, CD, CRa, SiH, SiD, SiRa, GeH, GeD, GeRd, P, P═O, As, As═O, Bi or Bi═O;
wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 may represent mono-, di, tri, tetra-substitutions, or no substitution, and R1, R2, R3, R4, R5, R6, R7, R8, R9, Ra, Rb, Rc and Rd are independently selected from the group consisting hydrogen, deuterium, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, halogen, hydroxyl, thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, nitrile, isonitrile, heteroary, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphoramide, amercapto, sulfo, carboxyl, hydrzino, substituted silyl, or any conjugate or combination thereof; Two or more adjacent R1, R2, R3, R4, R5, R6, R7, R8 and R9 are optionally joined to form a fused ring;
wherein Ra, Rb, Rc and Rd may represent mono-, di, tri, tetra-substitutions, or no substitution, and Ra, Rb, Rc and Rd are independently selected from the group consisting hydrogen, deuterium, aryl, cycloalkyl, cycloalkenyl, heterocyclyl, heteroaryl, alkyl, alkenyl, alkynyl, halogen, hydroxyl, thiol, nitro, cyano, amino, a mono- or di-alkylamino, a mono- or diaryl amino, alkoxy, aryloxy, haloalkyl, aralkyl, ester, nitrile, isonitrile, heteroary, alkoxycarbonyl, acylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfonylamino, sulfamoyl, carbamoyl, alkylthio, sulfinyl, ureido, phosphorannide, annercapto, sulfo, carboxyl, hydrzino, substituted silyl, or any conjugate or combination thereof.

### Claim 2 (depends on 1)

The compound as described in claim 1, wherein
is selected from the group consisting

### Claim 3 (depends on 1)

The compound as described in claim 1, wherein the compound has the structure of Formula III, Formula IV, Formula V, or Formula VI:

### Claim 4 (depends on 1)

The compound as described in claim 1, wherein the compound has the structure of from Compound 1-Compound 246:

### Claim 5 (depends on 1)

A device comprising the composition as described in claim 1.

### Claim 6 (depends on 5)

The device as described in claim 5, wherein the device comprises a full color display.

### Claim 7 (depends on 5)

The device as described in claim 5, wherein the device is a photovoltaic device.

### Claim 8 (depends on 5)

The device as described in claim 5, wherein the device is a luminescent display device.

### Claim 9 (depends on 5)

The device as described in claim 5, wherein the device comprises an organic light emitting diode (OLED).

### Claim 10 (depends on 9)

The device as described in claim 9, wherein the device comprises a phosphorescent organic light emitting diode.

### Claim 11 (depends on 9)

The device as described in claim 9, wherein the device is a phosphorescent organic light emitting diode.

### Claim 12 (depends on 1)

A light emitting device comprising the composition as described in claim 1.

### Claim 13 (depends on 4)

The device as described in claim 4, wherein the compound is selected to have 100% internal quantum efficiency in the device settings.