US-12617806-B2 - Organic electroluminescent materials and devices

US12617806B2US 12617806 B2US12617806 B2US 12617806B2US-12617806-B2

Abstract

The present disclosure provides amide M carbene emitters of Formula (I); organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer, disposed between the anode and the cathode, comprising a compound of Formula (1); and consumer products comprising an OLED comprising a compound of Formula (I):

Inventors

Peter I. Djurovich
Mark E. Thompson
Narcisse Ukwitegetse
Anton Razgniaev

Assignees

THE UNIVERSITY OF SOUTHERN CALIFORNIA

Dates

Publication Date: 20260505
Application Date: 20210715

Claims (13)

1 . A compound of formula (I): wherein M is a metal; ring B is one of the following carbene ligands: wherein each X 25 to X 28 independently represents N or C; R 3 represents mono to the maximum allowable substitution; each occurrence of R 1 to R 3 is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R 1 to R 3 are optionally joined or fused together to form a ring which is optionally substituted; and the dashed line inside the five-member ring represents zero or one double-bond; R represents mono to the maximum allowable substitution; each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R are optionally joined or fused together to form a ring which is optionally substituted; provided that ring B is not and provided that when ring B is then R 1 is not aryl substituted with aryl; ring A is an amide ligand selected from the group consisting of formula (Ai) and formula (Aii); wherein, in formula (Ai), the dashed line represents coordination to M; each X 5 , X 6 , X 7 , and X 8 independently represents N or C; R A represents mono to the maximum allowable substitution; wherein at least one pair atoms selected from the group consisting of X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 each represent C, wherein the respective adjacent groups R A together form a fused ring having the following formula: wherein each X 1 , X 2 , X 3 , and X 4 independently represents N or C; n is 0 or 1; wherein when n is 0, then X 3 binds directly to formula (Ai); R B represents mono to the maximum allowable substitution; each occurrence of R A and R B is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof; wherein at least two adjacent X 1 to X 4 represent C, wherein the respective adjacent R B are joined or fused together to form an aryl or heteroaryl ring, wherein the aryl or heteroaryl ring is optionally substituted and optionally comprises additional ring fusions; wherein any two adjacent R A are optionally joined or fused together to form a ring which is optionally substituted; wherein, in formula (Aii); each X 11 to X 18 independently represents N or C; R A and R B each represent mono to the maximum allowable substitution; and each occurrence of R A and R B is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof; wherein any two adjacent R A and R B are optionally joined or fused together to form a ring which is optionally substituted.
2 . The compound of claim 1 , wherein M is selected from the group consisting of Cu, Ag, and Au.
3 . The compound of claim 1 , wherein ring A is represented by formula (Aii).
4 . The compound of claim 1 , wherein ring A is represented by one of the following structures:
5 . The compound of claim 1 , wherein ring A is represented by formula (Ai).
6 . The compound of claim 1 , wherein ring A is selected from the group consisting of: wherein the dashed line represents coordination to M; each occurrence of X 1 to X 20 independently represents C or N; each occurrence of R B to R G independently represents mono to the maximum allowable substitution; each occurrence of R A to R F is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R A to R F are optionally joined or fused together to form a ring which is optionally substituted.
7 . The compound of claim 6 , wherein each of X 1 to X 20 independently represents C.
8 . The compound of claim 1 , wherein ring A is selected from the group consisting of:
9 . The compound of claim 1 , wherein ring B is:
10 . The compound of claim 1 , wherein the compound is selected from the group consisting of: wherein Dipp represents 2,6-disopropylphenyl.
11 . An organic light emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a compound of formula (I) wherein M is a metal; ring B is a one of the following carbene ligands: wherein each X 25 to X 28 independently represents N or C; R 3 represents mono to the maximum allowable substitution; each occurrence of R 1 to R 3 is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R 1 to R 3 are optionally joined or fused together to form a ring which is optionally substituted; and the dashed line inside the five-member ring represents zero or one double-bond; R represents mono to the maximum allowable substitution; each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R are optionally joined or fused together to form a ring which is optionally substituted; provided that ring B is not and provided that when ring B is then R 1 is not aryl substituted with aryl; ring A is an amide ligand selected from the group consisting of formula (Ai) and formula (Aii); wherein, in formula (Ai), the dashed line represents coordination to M; each X 5 , X 6 , X 7 , and X 8 independently represents N or C; R A represents mono to the maximum allowable substitution; wherein at least one pair atoms selected from the group consisting of X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 each represent C, wherein the respective adjacent groups R A together form a fused ring having the following formula: wherein each X 1 , X 2 , X 3 , and X 4 independently represents N or C; n is 0 or 1; wherein when n is 0, then X 3 binds directly to formula (Ai); R B represents mono to the maximum allowable substitution; each occurrence of R A and R B is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof; wherein at least two adjacent X 1 to X 4 represent C, wherein the respective adjacent R B are joined or fused together to form an aryl or heteroaryl ring, wherein the aryl or heteroaryl ring is optionally substituted and optionally comprises additional ring fusions; wherein any two adjacent R A are optionally joined or fused together to form a ring which is optionally substituted; wherein, in formula (Aii); each X 11 to X 18 independently represents N or C; R A and R B each represent mono to the maximum allowable substitution; and each occurrence of R A and R B is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof; wherein any two adjacent R A and R B are optionally joined or fused together to form a ring which is optionally substituted.
12 . A consumer product comprising an organic light-emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a compound of formula (I): wherein M is a metal; ring B is one of the following carbene ligands: wherein each X 25 to X 28 independently represents N or C; R 3 represents mono to the maximum allowable substitution; each occurrence of R 1 to R 3 is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R 1 to R 3 are optionally joined or fused together to form a ring which is optionally substituted; and the dashed line inside the five-member ring represents zero or one double-bond; R represents mono to the maximum allowable substitution; each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R are optionally joined or fused together to form a ring which is optionally substituted; provided that ring B is not and provided that when ring B is then R 1 is not aryl substituted with aryl; ring A is an amide ligand selected from the group consisting of formula (Ai) and formula (Aii); wherein, in formula (Ai), the dashed line represents coordination to M; each X 5 , X 6 , X 7 , and X 8 independently represents N or C; R A represents mono to the maximum allowable substitution; wherein at least one pair atoms selected from the group consisting of X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 each represent C, wherein the respective adjacent groups R A together form a fused ring having the following formula: wherein each X 1 , X 2 , X 3 , and X 4 independently represents N or C; n is 0 or 1; wherein when n is 0, then X 3 binds directly to formula (Ai); R B represents mono to the maximum allowable substitution; each occurrence of R A and R B is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof; wherein at least two adjacent X 1 to X 4 represent C, wherein the respective adjacent R B are joined or fused together to form an aryl or heteroaryl ring, wherein the aryl or heteroaryl ring is optionally substituted and optionally comprises additional ring fusions; wherein any two adjacent R A are optionally joined or fused together to form a ring which is optionally substituted; wherein, in formula (Aii); each X 11 to X 18 independently represents N or C; R A and R B each represent mono to the maximum allowable substitution; and each occurrence of R A and R B is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano phosphino, and combinations thereof; wherein any two adjacent R A and R B are optionally joined or fused together to form a ring which is optionally substituted.
13 . A formulation comprising the compound of claim 1 .

Description

CROSS-REFERENCE TO RELATED APPLICATIONS The present application claims priority to U.S. Provisional Application No. 63/061,263, filed Aug. 5, 2020, which is incorporated by reference herein in its entirety. FIELD The present disclosure relates to compounds for use as emitters, and devices, such as organic light emitting diodes, including the same. PARTIES TO A JOINT RESEARCH AGREEMENT The claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: Regents of the University of Michigan, Princeton University, University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement. BACKGROUND Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants. OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety. Efficient emitters with high radiative rates are critical for high performance display technologies and solid-state lighting applications. Blue-emitting materials for OLEDs are particularly problematic due to the required high energy that leads to detrimental photophysical processes (TTA & TPA) and chemical decomposition of the materials. While decreasing the emission lifetime is key solutions to this issue, today's widely used heavy-metal phosphors (e.g Ir3+, Pt+2complexes) inherently fail to have lifetimes below 1 s due to the nature of spin-orbit coupling (SOC) contribution in the triplet harvesting events. That is, SOC that helps fast intersystem crossing events between singlets and triplets does eventually induce large zero-field splitting (ZFS) between triplet sublevels hampering fast equilibration of triplet states for harvest. Early developed organic and inorganic thermally activated delayed fluorescence (TADF) alternatives also suffer similar long-lived excitons (microsecond regime), but now due to the counteractive relationship between the required small singlet-triplet separation (ΔEST<0.12 eV) and large oscillator strength for short τTADF. One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Alternatively the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can be either a single EML device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art. One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy)3, which has the following structure: In this, and later figures herein, we depict the dative bond from nitrogen to metal (here, Ir) as a straight line. SUMMARY The present disclosure provides a compound of formula (I): whereinM is a metal;ring B is a carbene ligand;R represents mono to the maximum allowable substitution;each R is independently hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, acyl, carboxylic acid, ether, ester, sulfinyl, sulfonyl, cyano, phosphino, and combinations thereof; wherein any two adjacent R are optionally joined or fused together to form a ring which is optionally substituted;ring A is an amide li