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US 2026/0085084 A1Published application
Judicious Design of Benzo-carbene Based Metal Complex Emitters For Fast Radiative Organic Light Emitting Diodes
AssigneeArizona Board of Regents on behalf of Arizona State University
InventorsJian Li, Qian Wang
Life of this patent
Estimating the term…
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.
Claims20
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.
25 more elements
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.
29 more elements
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.
29 more elements
Dependencies are inferred from the claim text.