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US 2026/0107679 A1Published application
Organic electroluminescent materials and devices
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 represented by Formula I:
- wherein:
- M represents platinum (Pt) or palladium (Pd);
- Y1, Y2, Y4, Y5, Y6, Y7, Y8, and Y9 each independently represent N or C;
- X1 and X2 are coordinated with M and independently represent N or C;
- Ar1 represents heteroaryl or N-heterocyclic carbene;
- Ar2 represents aryl, or heteroaryl;
- Ar3 and Ar1 are each independently absent or present;
- wherein each Ar3 and Ar1 present independently represents substituted or unsubstituted aryl or heteroaryl;
- B2 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, and Bi;
- wherein when Ar1 represents N-heterocyclic carbene, then Ar3 is absent and B1 represents a single bond connecting Ar1 and Ar2;
- wherein when Ar1 represents heteroaryl, then Ar3 is present and B1 is selected from the group consisting of CR11, SiR11, GeR8, N, P, P═O, As, As═O, B, and R10Bi═O;
- or Ar3 is not present and B1 is selected from the group consisting of 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, and R14Bi═O;
- wherein when Ar4 is absent, then A2 is absent and B3 is A4;
- wherein when Ar4 is present, then B3 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, and 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, R4P═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, sulfonyl, 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 A6 and A7 is independently a single bond, CR17R18, CR17=CR88, 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 R5, 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;
- wherein one or more of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, and R19 optionally represents RX;
- each occurrence of n is zero to the maximum number of substituents on the corresponding ring;
- RX3 is a substituent on Ar3 positioned ortho to the bond to B1;
- RX, RX1, RX2, and RX3 each 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 RX, RX1, RX2, and RX3 do not join to form a fused ring with adjacent substituents;
- and
- provided that when Ar1 represents N-heterocyclic carbene, then RX1 is selected from the group consisting of cycloalkyl, bicyclo, fused bicyclo, adamantyl, ferrocenyl, dialkylamino, diarylamino, alkylarylamino, trialkylsilyl, tricycloalkylsilyl, triheteroarylsilyl, alkyldiarylsilyl, alkylarylamino, substituted aryl, and substituted heteroaryl.
26 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 comprising a compound represented by Formula I:
- wherein:
- M represents platinum (Pt) or palladium (Pd);
- Y1, Y2, Y4, Y5, Y6, Y7, Y8, and Y9 each independently represent N or C;
- X1 and X2 are coordinated with M and independently represent N or C;
- Ar1 represents heteroaryl or N-heterocyclic carbene;
- Ar2 represents aryl, or heteroaryl;
- Ar3 and Ar1 are each independently absent or present;
- wherein each Ar3 and Ar1 present independently represents substituted or unsubstituted aryl or heteroaryl;
- B2 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, and Bi;
- wherein when Ar1 represents N-heterocyclic carbene, then Ar3 is absent and B1 represents a single bond connecting Ar1 and Ar2;
- wherein when Ar1 represents heteroaryl, then Ar3 is present and B1 is selected from the group consisting of CR11, SiR11, GeR8, N, P, P═O, As, As═O, B, and R10Bi═O;
- or Ar3 is not present and B1 is selected from the group consisting of 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, and R14Bi═O;
- wherein when Ar4 is absent, then A2 is absent and B3 is A4;
- wherein when Ar4 is present, then B3 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, and 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, R4P═O, AsR14, R14As═O, O, S, S═O, SO2, Se, Se═O, SeO2, BR14, BiR14, R14Bi═O,
- each of R1, R2, R3, R4, R1, 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, sulfonyl, 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 A6 and A7 is independently a single bond, CR1R8, 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 R5, 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;
- wherein one or more of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R13, R16, R7, R18, and R19 optionally represents RX;
- each occurrence of n is zero to the maximum number of substituents on the corresponding ring;
- RX3 is a substituent on Ar3 positioned ortho to the bond to B1;
- RX, RX1, RX2, and RX3 each 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 RX, RX1, RX2, and RX3 do not join to form a fused ring with adjacent substituents;
- and
- provided that when Ar1 represents N-heterocyclic carbene, then RX1 is selected from the group consisting of cycloalkyl, bicyclo, fused bicyclo, adamantyl, ferrocenyl, dialkylamino, diarylamino, alkylarylamino, trialkylsilyl, tricycloalkylsilyl, triheteroarylsilyl, alkyldiarylsilyl, alkylarylamino, substituted aryl, and substituted heteroaryl.
30 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 comprising a compound represented by Formula I:
- wherein:
- M represents platinum (Pt) or palladium (Pd);
- Y1, Y2, Y4, Y5, Y6, Y7, Y8, and Y9 each independently represent N or C;
- X1 and X2 are coordinated with M and independently represent N or C;
- Ar1 represents heteroaryl or N-heterocyclic carbene;
- Ar2 represents aryl, or heteroaryl;
- Ar3 and Ar1 are each independently absent or present;
- wherein each Ar3 and Ar1 present independently represents substituted or unsubstituted aryl or heteroaryl;
- B2 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, and Bi;
- wherein when Ar1 represents N-heterocyclic carbene, then Ar3 is absent and B1 represents a single bond connecting Ar1 and Ar2;
- wherein when Ar1 represents heteroaryl, then Ar3 is present and B1 is selected from the group consisting of CR8, SiR8, GeR8, N, P, P═O, As, As═O, B, and R10Bi═O;
- or Ar3 is not present and B1 is selected from the group consisting of 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, and R14Bi═O;
- wherein when Ar4 is absent, then A2 is absent and B3 is A4;
- wherein when Ar4 is present, then B3 is selected from the group consisting of CR11, SiR11, GeR11, N, P, P═O, As, As═O, B, R11Bi═O, and 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, R4P═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, sulfonyl, 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 A6 and A7 is independently a single bond, CR17R18, CR7=CR18, C≡C, C═O, C═S, SiR17R1B, 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 R13, R16, R17, R18, and R19 is independently absent or present as a single substituent or multiple substituents, valency permitting, and each R13, 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;
- wherein one or more of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R13, R16, R17, R18, and R19 optionally represents RX;
- each occurrence of n is zero to the maximum number of substituents on the corresponding ring;
- RX3 is a substituent on Ar3 positioned ortho to the bond to B1;
- RX, RX1, RX2, and RX3 each 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 RX, RX1, RX2, and RX3 do not join to form a fused ring with adjacent substituents;
- and
- provided that when Ar1 represents N-heterocyclic carbene, then RX1 is selected from the group consisting of cycloalkyl, bicyclo, fused bicyclo, adamantyl, ferrocenyl, dialkylamino, diarylamino, alkylarylamino, trialkylsilyl, tricycloalkylsilyl, triheteroarylsilyl, alkyldiarylsilyl, alkylarylamino, substituted aryl, and substituted heteroaryl.
30 more elements
Dependencies are inferred from the claim text.