# US 2026/0085084 A1 · Judicious Design of Benzo-carbene Based Metal Complex Emitters For Fast Radiative Organic Light Emitting Diodes

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- Number: US 2026/0085084 A1
- Document ID: US20260085084A1
- Status: Published application
- Kind: A1
- Application number: 19/338,530
- Filed: 2025-09-24
- Published: 2026-03-26
- Earliest claimed: 2024-09-24
- Assignees: Arizona Board of Regents on behalf of Arizona State University
- Applicants: Arizona Board of Regents on behalf of Arizona State University
- Inventors: Jian Li; Qian Wang
- Web page: https://patentgrep.com/patent/US20260085084A1

## CPC

- C07F 15/0086: {Platinum compounds}
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/12: comprising dopants
- H10K 85/342: {comprising iridium}
- H10K 85/346: {comprising platinum}
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 2101/10: Triplet emission
- 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

## Abstract

Provided are compounds of Formula I. Also provided are formulations comprising these compounds. Further provided are OLEDs and related consumer products that utilize these compounds.

## Claims

### Claim 1

A compound of Formula I:
wherein:
M represents platinum (Pt) or palladium (Pd);
Y1 and Y2 independently represent N or CR7;
Y3 and Y4 independently represent N or CR6;
X1 and X2 are coordinated with M and independently represent N or C;
Cy1 and Cy2 each independently represents substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, or N-heterocyclic carbene;
Cy3 and Cy4 are each independently absent or present; wherein each Cy3 and Cy5 present independently represents substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, or N-heterocyclic carbene;
wherein when Cy3 is absent, then B1 is selected from the group consisting of CR8R9, CR8═CR9, C≡C, C═O, C═S, SiR8R9, GeR8R9, NR10, PR10, R10P═O, AsR10, R10As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR10, BiR10, R10Bi═O,
or B1 is not present and Cy1 and Cy2 are connected by a single bond;
wherein when Cy3 is present, then B1 is selected from the group consisting of CR8, SiR8, GeR8, N, P, P═O, As, As═O, B, R10Bi═O, or Bi, or B1 is not present and Cy1 and Cy2 are connected by a single bond;
wherein when Cy4 is absent, then A3 is absent and B2 is A4;
wherein when Cy4 is present, then B2 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, or Bi;
each of A1, A2, A3, and A4 is independently absent or present, and each of A1, A2, A3, and A4 present represents a single bond, CR12R13, CR12═CR13, C≡C, C═O, C═S, SiR12R13, GeR12R13, NR12, PR13, R14P═O, AsR14, R14As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR14, BiR14, R14Bi═O,
each of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, and R14 independently represents independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein any two adjacent substituents optionally join to form a fused ring of Formula A, Formula B, Formula C, or Formula D:
each of A5 and A6 is independently a single bond, CR17R18, CR17═CR18, C≡C, C═O, C═S, SiR17R18, GeR17R18, NR19, PR19, R19P═O, AsR19, R19As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR19, BiR19, R19Bi═O,
each of Z1, Z2, Z3, Z4, Z5, and Z6 is independently N or C.
each R15, R16, R17, R18, and R19 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each R15, R16, R17, R18, and R19 present independently represents a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; wherein any two adjacent substituents may further join to form a fused ring;
each occurrence of n independently represents zero to the maximum number of substituents;
wherein one or more of R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, R12, R13, R14, R15, R16, R1, R18, and R19 optionally represents RX;
wherein each RX independently represents a bulky substituent selected from the group consisting branched alkyl, cycloalkyl, bicyclo, fused bicyclo, adamantyl, ferrocenyl, dialkylamino, diarylamino, alkylarylamino, trialkylsilyl, tricycloalkylsilyl, triarylsilyl, triheteroarylsilyl, dialkylarylsilyl, alkyldiarylsilyl, alkylarylamino, and optionally substituted: aryl and heteroaryl;
wherein RY1 and RY2 independently represent optionally substituted: aryl or heteroaryl, wherein the substituent is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; wherein any two adjacent substituents may further join to form a fused ring;
provided that adjacent groups RX, RY1, and RY2 do not join to form a ring.

### Claim 2 (depends on 1)

The compound of claim 1, wherein RY1 is represented by Formula 1; and wherein RY2 is represented by Formula 2:
wherein:
the hashed line indicates the bond to Formula I;
X1, X2, X3, X4, X5, X6, X7, X8, X9, and X10 are independently selected from the group consisting of C and N; wherein when any of X1, X2, X3, X4, X5, X6, X7, X8, X9, and X10 represents N then the corresponding substituent RX1 to RX10 is not present;
RX1, RX2, RX3, RX4, RX5, RX6, RX7, RX8, RX9, and RX10 independently represent a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; wherein any two adjacent substituents RX1, RX2, RX3, RX4, and RX5 or any two adjacent substituents RX6, RX7, RX8, RX9, and RX10 may further join to form a fused ring of Formula A, Formula B, Formula C, or Formula D.

### Claim 3 (depends on 2)

The compound of claim 2, wherein X1, X2, X3, X4, X5, X6, X7, X8, X9, and X10 are each C; and RX1, RX2, RX3, RX4, RX5, RX6, RX7, RX8, RX9, and RX10 independently represent a hydrogen or deuterium.

### Claim 4 (depends on 2)

The compound of claim 2, wherein X1 and X5 are each C; and RX1 and RX5 independently represent a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, arylalkyl, alkoxy, silyl, aryl, heteroaryl, and combinations thereof.

### Claim 5 (depends on 2)

The compound of claim 2, wherein X6 and X10 are each C; and RX6 and RX10 independently represent a substituent selected from the group consisting of deuterium, alkyl, cycloalkyl, arylalkyl, alkoxy, silyl, aryl, heteroaryl, and combinations thereof.

### Claim 6 (depends on 2)

The compound of claim 2, wherein at least one of X1, X2, X3, X4, X5, X6, X7, X8, X9, and X10 represents N.

### Claim 7 (depends on 1)

The compound of claim 1, wherein Cyl and Cy2, and Cy3 and Cy4 if present, independently represent substituted or unsubstituted aryl or heteroaryl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein X1 is N and Cy4 represents a heteroaryl selected from the group consisting of pyridine, imidazole, and pyrazole; or X1 is C and Cy4 represents benzimidazole carbene.

### Claim 9 (depends on 1)

The compound of claim 1, wherein A1 is present and represents

### Claim 10 (depends on 1)

The compound of claim 1, wherein A1 is not present.

### Claim 11 (depends on 1)

The compound of claim 1, wherein Cy4 is absent, A3 is absent, and B2 is A4.

### Claim 12 (depends on 1)

The compound of claim 1, wherein Cyl is substituted with at least one group R1 at the position para to X1.

### Claim 13 (depends on 12)

The compound of claim 12, wherein R1 represents substituted or unsubstituted: alkyl, aryl, or heteroaryl.

### Claim 14 (depends on 1)

The compound of claim 1, wherein the compound is represented by one of Formula II, Formula III, Formula IV, or Formula V:

### Claim 15 (depends on 1)

The compound of claim 1, wherein the compound is represented by one of the following structures:
wherein each Y5, Y6, Y7, Y8, Y9, Y10, Y11, Y12, Y13, Y14, Y15, and Y16 represents C or N.

### Claim 16 (depends on 1)

The compound of claim 1, wherein the compound is represented by one of the following structures:
wherein each Y5, Y6, Y7, Y8, Y9, Y10, Y11, Y12, Y13, Y14, Y15, Y16, Y17, Y18, Y19, Y20, Y21, and Y22 represents C or N.

### Claim 17 (depends on 1)

The compound of claim 1, wherein the compound is represented by one of the following structures:

### Claim 18

An organic electroluminescent device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound of Formula I:
wherein:
M represents platinum (Pt) or palladium (Pd);
Y1 and Y2 independently represent N or CR7;
Y3 and Y4 independently represent N or CR6;
X1 and X2 are coordinated with M and independently represent N or C;
Cy1 and Cy2 each independently represents substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, or N-heterocyclic carbene;
Cy3 and Cy4 are each independently absent or present; wherein each Cy3 and Cy5 present independently represents substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, or N-heterocyclic carbene;
wherein when Cy3 is absent, then B1 is selected from the group consisting of CR8R9, CR8═CR9, C≡C, C═O, C═S, SiR8R9, GeR8R9, NR10, PR10, R10P═O, AsR10, R10As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR10, BiR10, R10Bi═O,
or B1 is not present and Cy1 and Cy2 are connected by a single bond;
wherein when Cy3 is present, then B1 is selected from the group consisting of CR8, SiR8, GeR8, N, P, P═O, As, As═O, B, R10Bi═O, or Bi, or B1 is not present and Cy1 and Cy2 are connected by a single bond;
wherein when Cy4 is absent, then A3 is absent and B2 is A4;
wherein when Cy4 is present, then B2 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, or Bi;
each of A1, A2, A3, and A4 is independently absent or present, and each of A1, A2, A3, and A4 present represents a single bond, CR12R13, CR12═CR13, C≡C, C═O, C═S, SiR12R13, GeR12R13, NR12, PR13, R14P═O, AsR14, R14As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR14, BiR14, R14Bi═O,
each of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, and R14 independently represents independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein any two adjacent substituents optionally join to form a fused ring of Formula A, Formula B, Formula C, or Formula D:
each of A5 and A6 is independently a single bond, CR17R18, CR17═CR18, C≡C, C═O, C═S, SiR17R18, GeR17R18, NR19, PR19, R19P═O, AsR19, R19As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR19, BiR19, R19Bi═O,
each of Z1, Z2, Z3, Z4, Z5, and Z6 is independently N or C.
each R15, R16, R17, R18, and R19 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each R15, R16, R17, R18, and R19 present independently represents a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; wherein any two adjacent substituents may further join to form a fused ring;
each occurrence of n independently represents zero to the maximum number of substituents;
wherein one or more of R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, R12, R13, R14, R15, R16, R17, R18, and R19 optionally represents RX;
wherein each RX independently represents a bulky substituent selected from the group consisting branched alkyl, cycloalkyl, bicyclo, fused bicyclo, adamantyl, ferrocenyl, dialkylamino, diarylamino, alkylarylamino, trialkylsilyl, tricycloalkylsilyl, triarylsilyl, triheteroarylsilyl, dialkylarylsilyl, alkyldiarylsilyl, alkylarylamino, and optionally substituted: aryl and heteroaryl;
wherein RY1 and RY2 independently represent optionally substituted: aryl or heteroaryl, wherein the substituent is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; wherein any two adjacent substituents may further join to form a fused ring;
provided that adjacent groups RX, RY1, and RY2 do not join to form a ring.

### Claim 19 (depends on 18)

The OLED of claim 18, wherein the compound is a sensitizer, and the OLED further comprises an acceptor selected from the group consisting of a fluorescent emitter, a delayed fluorescence emitter, and combination thereof.

### Claim 20

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 represents platinum (Pt) or palladium (Pd);
Y1 and Y2 independently represent N or CR7;
Y3 and Y4 independently represent N or CR6;
X1 and X2 are coordinated with M and independently represent N or C;
Cy1 and Cy2 each independently represents substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, or N-heterocyclic carbene;
Cy3 and Cy4 are each independently absent or present; wherein each Cy3 and Cy5 present independently represents substituted or unsubstituted aryl, cycloalkyl, cycloalkenyl, heteroaryl, heterocyclyl, or N-heterocyclic carbene;
wherein when Cy3 is absent, then B1 is selected from the group consisting of CR8R9, CR8═CR9, C≡C, C═O, C═S, SiR8R9, GeR8R9, NR10, PR10, R10P═O, AsR10, R10As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR10, BiR10, R10Bi═O,
or B1 is not present and Cy1 and Cy2 are connected by a single bond;
wherein when Cy3 is present, then B1 is selected from the group consisting of CR8, SiRB, GeRB, N, P, P═O, As, As═O, B, R10Bi═O, or Bi, or B1 is not present and Cy1 and Cy2 are connected by a single bond;
wherein when Cy4 is absent, then A3 is absent and B2 is A4;
wherein when Cy4 is present, then B2 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, or Bi;
each of A1, A2, A3, and A4 is independently absent or present, and each of A1, A2, A3, and A4 present represents a single bond, CR12R13, CR12═CR13, C≡C, C═O, C═S, SiR12R13, GeR12R13, NR12, PR13, R14P═O, AsR14, R14As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR14, BiR14, R14Bi═O,
each of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, and R14 independently represents independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof;
wherein any two adjacent substituents optionally join to form a fused ring of Formula A, Formula B, Formula C, or Formula D:
each of A5 and A6 is independently a single bond, CR17R18, CR17═CR18, C≡C, C═O, C═S, SiR17R18, GeR17R18, NR19, PR19, R19P═O, AsR19, R19As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR19, BiR19, R19Bi═O,
each of Z1, Z2, Z3, Z4, Z5, and Z6 is independently N or C.
each R15, R16, R17, R18, and R19 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each R15, R16, R17, R18, and R19 present independently represents a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; wherein any two adjacent substituents may further join to form a fused ring;
each occurrence of n independently represents zero to the maximum number of substituents;
wherein one or more of R1, R2, R3, R4, R5, R6, R7, R8, R9, R11, R12, R13, R14, R15, R16, R17, R18, and R19 optionally represents RX;
wherein each RX independently represents a bulky substituent selected from the group consisting branched alkyl, cycloalkyl, bicyclo, fused bicyclo, adamantyl, ferrocenyl, dialkylamino, diarylamino, alkylarylamino, trialkylsilyl, tricycloalkylsilyl, triarylsilyl, triheteroarylsilyl, dialkylarylsilyl, alkyldiarylsilyl, alkylarylamino, and optionally substituted: aryl and heteroaryl;
wherein RY1 and RY2 independently represent optionally substituted: aryl or heteroaryl, wherein the substituent is selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, boryl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; wherein any two adjacent substituents may further join to form a fused ring;
provided that adjacent groups RX, RY1, and RY2 do not join to form a ring.