Organic electroluminescent materials and devices
Provided are organometallic compounds comprising two moieties A and B which are each independently a monocyclic ring or a polycyclic fused ring structure, wherein the monocyclic ring or each ring of the polycyclic fused ring structure is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring which are linked by a direct bond and which are further bridged by a linker comprising two groups which are each independently selected from the group consisting of O, S, Se, NR, BR, BRR′, PR, CR, C═O, C═NR, C═CRR′, C═S, CRR′, SO, SO 2 , P(O)R, SiRR′, and GeRR′. Also provided are formulations comprising these organometallic compounds. Further provided are organic light emitting devices (OLEDs) and related consumer products that utilize these organometallic compounds.
1 . A compound comprising a first ligand L A ;
wherein L A comprises a structure R of Formula I:
wherein moieties A and B are each independently a monocyclic ring or a polycyclic fused ring structure, wherein the monocyclic ring or each ring of the polycyclic fused ring structure is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
wherein Y 1 and Y 2 are each independently selected from the group consisting of O, S, Se, NR, BR, BRR′, PR e , CR, C═O, C═NR, C═CRR′, C═S, CRR′, SO, SO 2 , P(O)R, SiRR′, and GeRR′;
wherein each of R A and R B independently represents mono to the maximum allowable substitution, or no substitution;
wherein L A is coordinated to a metal M;
wherein moiety A and moiety B are not both joined to M by direct bonds;
wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
wherein M may be coordinated to other ligands;
wherein L A may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein any two substituents may be joined or fused to form a ring;
with the proviso that if moiety A is a pyridine ring joined to Ir by an Ir—N bond, then Y′ is not CF 2 and Y 2 is not CRR′; and
with the proviso that if moiety A is a benzene ring joined to Ir by a direct bond, then Y 1 is not O and Y 2 is not CRR′;
wherein each R, R′, R A and R B is independently 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.
2 . The compound of claim 1 , wherein the first ligand L A has Formula II:
wherein moiety C is a monocyclic ring comprising one 5-membered to 10-membered carbocyclic or heterocyclic ring, or a polycyclic fused ring structure comprising at least two 5-membered to 10-membered carbocyclic or heterocyclic rings;
wherein Z 1 -Z 4 are each independently C or N;
wherein K 1 and K 2 are each independently selected from the group consisting of a direct bond, O, S, N(R α ), P(R α ), B(R α ), C(R α )(R β ), and Si(R α )(R β );
wherein L is a direct bond or an organic linker,
wherein R C represents mono to the maximum allowable substitution, or no substitution;
wherein each R α , R β , and R C is independently 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 two R A substituents are joined to form a structure of Formula III fused to ring A:
wherein moieties A and B, R A , R B , Y 1 , and Y 2 are as defined above.
3 . The compound of claim 1 , wherein each R, R′, R α , R β , R A , R B ; and R C is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
4 . The compound of claim 2 , wherein moiety A is an aromatic ring; and/or wherein moieties A and B are both aromatic rings; and/or wherein moiety C is a 6-membered aromatic ring; and/or wherein at least one of moieties A, B and C is a 5-membered ring.
5 . The compound of claim 1 , wherein Y 1 and Y 2 are independently selected from the group consisting of O, S, NR, CRR′, and SiRR′; and/or wherein both of K 1 and K 2 are a direct bond or wherein one of K 1 and K 2 is O; and/or wherein at least one of Z 1 -Z 4 is N; and/or wherein two R C are joined to form a ring.
6 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of the structures of LIST 1 as defined herein;
wherein each of R AA independently represents mono to the maximum allowable substitution, or no substitution;
each R AA is independently 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; and
any two substituents can be joined or fused to form a ring.
7 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of the structures of LIST 2 as defined herein;
wherein each of R CC independently represents mono to the maximum allowable substitution, or no substitution;
each R e , R f , R N , and R CC is independently 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;
Y A is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, C═S, C═Se, S═O, SO 2 , P(O)R e , C═NR e C═CR e R f , CR e R f , SiR e R f , and GeR e R f , and
any two substituents can be joined or fused to form a ring.
8 . The compound of claim 1 , wherein the ligand L A is selected from L Ai (R E )(R F )(W)(G) consisting of the structures of the following LIST 3:
L A
Structure of L A
L A1 -(R 1 )(R 1 )(W1)(G 1 ) to L A1 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A2 -(R 1 )(R 1 )(W1)(G 1 ) to L A2 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A3 -(R 1 )(R 1 )(W1)(G 1 ) to L A3 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A4 -(R 1 )(R 1 )(W1)(G 1 ) to L A4 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A5 -(R 1 )(R 1 )(W1)(G 1 ) to L A5 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A6 -(R 1 )(R 1 )(W1)(G 1 ) to L A6 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A7 -(R 1 )(R 1 )(W1)(G 1 ) to L A7 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A8 -(R 1 )(R 1 )(W1)(G 1 ) to L A8 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A9 -(R 1 )(R 1 )(W1)(G 1 ) to L A9 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A10 -(R 1 )(R 1 )(W1)(G 1 ) to L A10 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A11 -(R 1 )(R 1 )(W1)(G 1 ) to L A11 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A12 -(R 1 )(R 1 )(W1)(G 1 ) to L A12 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A13 -(R 1 )(R 1 )(W1)(G 1 ) to L A13 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A14 -(R 1 )(R 1 )(W1)(G 1 ) to L A14 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A15 -(R 1 )(R 1 )(W1)(G 1 ) to L A15 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A16 -(R 1 )(R 1 )(W1)(G 1 ) to L A16 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A17 -(R 1 )(R 1 )(W1)(G 1 ) to L A17 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A18 -(R 1 )(R 1 )(W1)(G 1 ) to L A18 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A19 -(R 1 )(R 1 )(W1)(G 1 ) to L A19 - (R 89 )(R 89 )(W36)(G 25 ) have the structure
L A20 -(R 1 )(R 1 )(W1)(G 1 ) to L A20 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A21 -(R 1 )(R 1 )(W1)(G 26 ) to L A21 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A22 -(R 1 )(R 1 )(W1)(G 26 ) to L A22 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A23 -(R 1 )(R 1 )(W1)(G 26 ) to L A23 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A24 -(R 1 )(R 1 )(W1)(G 26 ) to L A24 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A25 -(R 1 )(R 1 )(W1)(G 26 ) to L A25 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A26 -(R 1 )(R 1 )(W1)(G 26 ) to L A26 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A27 -(R 1 )(R 1 )(W1)(G 26 ) to L A27 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A28 -(R 1 )(R 1 )(W1)(G 26 ) to L A28 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A29 -(R 1 )(R 1 )(W1)(G 26 ) to L A29 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A30 -(R 1 )(R 1 )(W1)(G 26 ) to L A30 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A31 -(R 1 )(R 1 )(W1)(G 1 ) to L A31 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A32 -(R 1 )(R 1 )(W1)(G 1 ) to L A32 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A33 -(R 1 )(R 1 )(W1)(G 1 ) to L A33 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A34 -(R 1 )(R 1 )(W1)(G 1 ) to L A34 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A35 -(R 1 )(R 1 )(W1)(G 1 ) to L A35 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A36 -(R 1 )(R 1 )(W1)(G 1 ) to L A36 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A37 -(R 1 )(R 1 )(W1)(G 1 ) to L A37 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A38 -(R 1 )(R 1 )(W1)(G 1 ) to L A38 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A39 -(R 1 )(R 1 )(W1)(G 26 ) to L A39 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A40 -(R 1 )(R 1 )(W1)(G 26 ) to L A40 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A41 -(R 1 )(R 1 )(W1)(G 1 ) to L A41 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A42 -(R 1 )(R 1 )(W1)(G 1 ) to L A42 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A43 -(R 1 )(R 1 )(W1)(G 1 ) to L A43 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A44 -(R 1 )(R 1 )(W1)(G 1 ) to L A44 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A45 -(R 1 )(R 1 )(W1)(G 1 ) to L A45 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A46 -(R 1 )(R 1 )(W1)(G 1 ) to L A46 - (R 89 )(R 89 )(W42)(G 25 ) have the structure
L A47 -(R 1 )(R 1 )(W1)(G 26 ) to L A47 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A48 -(R 1 )(R 1 )(W1)(G 26 ) to L A48 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A49 -(R 1 )(R 1 )(W1)(G 26 ) to L A49 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A05 -(R 1 )(R 1 )(W1)(G 26 ) to L A50 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A51 -(R 1 )(R 1 )(W1)(G 26 ) to L A51 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
L A52 -(R 1 )(R 1 )(W1)(G 26 ) to L A52 - (R 89 )(R 89 )(W42)(G 53 ) have the structure
wherein, each of W1 to W42 representing Y 1 and Y 2 , is defined in the following LIST:
W1
W2
W3
W4
W5
W6
Y 1 = Ge(CH 3 ) 2 ;
Y 1 = O;
Y 1 = S;
Y 1 = S;
Y 1 = S;
Y 1 = S;
Y 2 = N(CH 3 ) 2
Y 2 = Si(CH 3 ) 2
Y 2 = Ge(CH 3 ) 2
Y 2 = C(CH 3 ) 2
Y 2 = Si(CH 3 ) 2
Y 2 = Ge(CH 3 ) 2
W7
W8
W9
W10
W11
W12
Y 1 = N(CH 3 );
Y 1 = N(CH 3 );
Y 1 = N(CH 3 );
Y 1 = Se;
Y 1 = Se;
Y 1 = Se;
Y 2 = C(CH 3 ) 2
Y 2 = Si(CH 3 ) 2
Y 2 = Ge(CH 3 ) 2
Y 2 = C(CH 3 ) 2
Y 2 = Si(CH 3 ) 2
Y 2 = Ge(CH 3 ) 2
W13
W14
W15
W16
W17
W18
Y 1 = C(CH 3 ) 2 ;
Y 1 = C(CH 3 ) 2 ;
Y 1 = C(CH 3 ) 2 ;
Y 1 = Si(CH 3 ) 2 ;
Y 1 = Si(CH 3 ) 2 ;
Y 1 = Si(CH 3 ) 2 ;
Y 2 = C(CH 3 ) 2
Y 2 = Si(CH 3 ) 2
Y 2 = Ge(CH 3 ) 2
Y 2 = C(CH 3 ) 2
Y 2 = Si(CH 3 ) 2
Y 2 = Ge(CH 3 ) 2
W19
W20
W21
W22
W23
W24
Y 1 = C(CH 3 ) 2 ;
Y 1 = C(CH 3 ) 2 ;
Y 1 = C(CH 3 ) 2 ;
Y 1 = Su(CH 3 ) 2 ;
Y 1 = Si(CH 3 ) 2 ;
Y 1 = Si(CH 3 ) 2 ;
Y 2 = O
Y 2 = S
Y 2 = Se
Y 2 = O
Y 2 = S
Y 2 = Se
W25
W26
W27
W28
W29
W30
Y 1 = Ge(CH 3 ) 2 ;
Y 1 = Ge(CH 3 ) 2 ;
Y 1 = Ge(CH 3 ) 2 ;
Y 1 = C(CH 3 ) 2 ;
Y 1 = Si(CH 3 ) 2 ;
Y 1 = O;
Y 2 = O
Y 2 = S
Y 2 = Se
Y 2 = N(CH 3 ) 2
Y 2 = N(CH 3 ) 2
Y 2 = C(CH 3 ) 2
W31
W32
W33
W34
W35
W36
Y 1 = CH 2 ;
Y 1 = CMe 2 ;
Y 1 = CH 2 ;
Y 1 = CMe 2 ;
Y 1 = CHF;
Y 1 = CHF;
Y 2 = CF 2
Y 2 = CF 2
Y 2 = CHF
Y 2 = CHF
Y 2 = CH 2
Y 2 = CMe 2
W37
W38
W39
W40
W41
W42
Y 1 = CF 2 ;
Y 1 = CHF;
Y 1 = CF 2 ;
Y 1 = CF 2 ;
Y 1 = CF 2 ;
Y 1 = C(CF 3 ) 2 ;
Y 2 = CHF
Y 2 = CHF
Y 2 = CF 2
Y 2 = CH 2
Y 2 = CMe 2
Y 2 = CH 2
wherein R 1 to R 89 have the structures in the following LIST:
and
wherein G 1 to G 53 have the structures in the following LIST:
9 . The compound of claim 1 , wherein the compound has a formula of M(L A ) p (L B ) q (L C ) r wherein L B and L C are each a bidentate ligand; and wherein p is 1, 2, or 3; q is 0, 1, or 2; r is 0, 1, or 2; and p+q+r is the oxidation state of the metal M.
10 . The compound of claim 9 , wherein the compound has a formula selected from the group consisting of Ir(L A ) 3 , Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), Ir(L A ) 2 (L C ), and Ir(L A )(L B )(L C ); and wherein L A , L B , and L C are different from each other, or a formula of Pt(L A )(L B ); and wherein L A and L B can be same or different.
11 . The compound of claim 9 , wherein L B and L C are each independently selected from the group consisting of the structures of LIST 4 as defined herein;
wherein:
T is selected from the group consisting of B, Al, Ga, and In;
wherein K 1′ is a direct bond or is selected from the group consisting of NR e , PR e , O, S, and Se;
each of Y 1 to Y 13 is independently selected from the group consisting of carbon and nitrogen;
Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, C═S, C═Se, S═O, SO 2 , P(O)R e , C═NR e , C═CR e R f , CR e R f , SiR e R f , and GeR e R f ,
R e and R f can be fused or joined to form a ring;
each R a , R b , R c , and R d independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; the general substituents defined herein; and any two adjacent R a , R b , R c , R d , R e and R f can be fused or joined to form a ring or form a multidentate ligand.
12 . The compound of claim 9 , wherein the compound has formula Ir(L A ) 3 , formula Ir(L A )(L B +) 2 , formula Ir(L A ) 2 (L Bk ), formula Ir(L A ) 2 (L Cj-I ), or, formula Ir(L A ) 2 (L Cj-II ),
wherein L A comprises a structure of Formula I;
wherein each L Bk has the structure as defined in LIST 6 as defined herein;
wherein each L Cj-I has a structure based on formula
and
each L Cj-II has a structure based on formula
wherein for each L Cj in L Cj-I and L Cj-II , R 201 and R 202 are each independently defined as in TABLE 1 as defined herein;
wherein R D1 to R D246 have the structures as defined in LIST 7 as defined herein.
13 . The compound of claim 9 , wherein the compound is selected from the group consisting of the structures of LIST 8 as defined herein.
14 . The compound of claim 9 , wherein the compound has the Formula IV:
wherein:
M 1 is Pd or Pt;
moieties E and F are each independently a monocyclic ring or a polycyclic fused ring structure, wherein the monocyclic ring or each ring of the polycyclic fused ring structure is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
Z 5 and Z 6 are each independently C or N;
K 1 , K 2 , K 3 , and K 4 are each independently selected from the group consisting of a direct bond, O, S, N(R α ), P(R α ), B(R α ), C(R α )(R β ), and Si(R α )(R β ), wherein at least two of them are direct bonds;
L 1 , L 2 , and L 3 are each independently absent or selected from the group consisting of a direct bond, BR, BRR′, NR, PR e , P(O)R, O, S, Se, C═O, C═S, C═Se, C═NR, C═CRR′, S═O, SO 2 , CR, CRR′, SiRR′, and GeRR′, wherein at least one of L 1 and L 2 is present;
R E and R F each independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of (R α ), (R β ), R′, R″, R E , and R F is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;
two adjacent R A , R B , R C , R E , and R F can be joined or fused together to form a ring where chemically feasible; and
moieties A and C, Z 1 -Z 4 , R A , and R B are all defined the same as above.
15 . The compound of claim 14 , wherein the compound is selected from the group consisting of compounds having the formula of Pt(L A′ )(L y ):
wherein L A′ is selected from the group consisting of the structures shown below:
wherein L A′ is selected from the group consisting of the structures in the following LIST:
wherein L y is selected from the group consisting of the structures shown below:
wherein X Z is BR e , NR e , PR e , O, S, Se, C═O, C═S, C═Se, S═O, SO 2 , P(O)R, C═NR e , C═CR e R f , CR e R f , SiR e R f , or GeR e R f ,
R N is 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;
the remaining variables are the same as previously defined; and
any two substituents may be optionally joined or fused to for a ring.
16 . The compound of claim 14 , wherein the compound is selected from the group consisting of the compounds having the formula of Pt(L A′ )(L y ):
wherein L A′ is selected from the group consisting of the structures shown below:
wherein L A′ is selected from the group consisting of L AY (R E )(R F )(R H )(W)(P), wherein i is an integer from 1 to 30, E, F, and H are each independently integers from 1 to 89 and each R 1 to R 89 has independently the structure as defined in the list of claim 8 , W is an integer from 1 to 42 as defined previously, and P is an integer from 1 to 5, wherein L A′1 (R 1 )(R 1 )(R 1 )(W1)(1) to L A′24 (R 89 )(R 89 )(R 89 )(W30)(5) have the structure defined in the following LIST:
L A′
Structure of L A′
L A′1 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′1 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′2 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′2 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′3 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′3 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′4 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′4 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′5 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′5 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′6 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′6 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′7 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′7 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′8 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′8 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′9 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′9 - (R 89 )(R 89 )(R 89 )(W30) (5)have the structure
L A′10 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′10 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′11 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′11 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′12 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′12 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′13 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′13 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′14 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′14 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′15 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′15 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′16 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′16 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′17 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′17 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′18 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′18 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′19 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′19 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′20 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′20 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′21 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′21 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′22 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′22 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′23 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′23 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′24 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′24 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′25 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′25 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′26 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′26 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′27 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′27 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′28 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′28 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′29 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′29 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
L A′30 - (R 1 )(R 1 )(R 1 )(W1)(1) to L A′30 - (R 89 )(R 89 )(R 89 )(W30) (5) have the structure
wherein, for each P from 1 to 5, L 1 has the meaning in the following LIST:
P = 1
P = 2
P = 3
P = 4
P = 5
L 1 = direct bond
L 1 = O
L 1 = S
L 1 = Se
L 1 = N(CH 3 )
wherein L y is selected from the group consisting of the structures shown below:
wherein L Y is selected from the group consisting of L Yw (R E (R F ), wherein w is an integer from 1 to 3, and E and F are each independently integers from 1 to 89,
wherein L Y1 (R 1 )(R 1 ) to L Y3 (R 89 )(R 89 ) have the structure defined in the following LIST:
L Y
Structure of L Y
for L Y1 (R E )(R F ), L Y1 (R 1 )(R 1 ) to L Y1 (R 89 )(R 89 ) have the structure
for L Y2 (R E )(R F ), L Y2 (R 1 )(R 1 ) to L Y2 (R 89 )(R 89 ) have the structure
for L Y3 (R E )(R F ), L Y3 (R 1 )(R 1 ) to L Y3 (R 89 )(R 89 ) have the structure
wherein R 1 to R 89 have the structures as defined in claim 8 .
17 . An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode,
wherein the organic layer comprises a A compound comprising a first ligand L A ;
wherein L A comprises a structure R of Formula I:
wherein moieties A and B are each independently a monocyclic ring or a polycyclic fused ring structure,
wherein the monocyclic ring or each ring of the polycyclic fused ring structure is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
wherein Y 1 and Y 2 are each independently selected from the group consisting of O, S, Se, NR, BR, BRR′, PR e , CR, C═O, C═NR, C═CRR′, C═S, CRR′, SO, SO 2 , P(O)R, SiRR′, and GeRR′;
wherein each of R A and R B independently represents mono to the maximum allowable substitution, or no substitution;
wherein L A is coordinated to a metal M;
wherein moiety A and moiety B are not both joined to M by direct bonds;
wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
wherein M may be coordinated to other ligands;
wherein L A may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein any two substituents may be joined or fused to form a ring;
with the proviso that if moiety A is a pyridine ring joined to Ir by an Ir—N bond, then Y 1 is not CF 2 and Y 2 is not CRR′; and
with the proviso that if moiety A is a benzene ring joined to Ir by a direct bond, then Y 1 is not O and Y 2 is not CRR′;
wherein each R, R′, R A and R B is independently 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.
18 . The OLED of claim 17 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5λ 2 -benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, triazine, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-5λ2-benzo[d]benzo[4,5]imidazo[3,2-a]imidazole, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).
19 . The OLED of claim 17 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of the following HOST group 1 as defined herein.
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,
wherein the organic layer comprises a compound comprising a first ligand L A ;
wherein L A comprises a structure R of Formula I:
wherein moieties A and B are each independently a monocyclic ring or a polycyclic fused ring structure,
wherein the monocyclic ring or each ring of the polycyclic fused ring structure is independently a 5-membered to 10-membered carbocyclic or heterocyclic ring;
wherein Y 1 and Y 2 are each independently selected from the group consisting of O, S, Se, NR, BR, BRR′, PR e , CR, C═O, C═NR, C═CRR′, C═S, CRR′, SO, SO 2 , P(O)R, SiRR′, and GeRR′;
wherein each of R A and R B independently represents mono to the maximum allowable substitution, or no substitution;
wherein L A is coordinated to a metal M;
wherein moiety A and moiety B are not both joined to M by direct bonds;
wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Pd, Ag, Au, and Cu;
wherein M may be coordinated to other ligands;
wherein L A may be joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;
wherein any two substituents may be joined or fused to form a ring;
with the proviso that if moiety A is a pyridine ring joined to Ir by an Ir—N bond, then Y 1 is not CF 2 and Y 2 is not CRR′; and
with the proviso that if moiety A is a benzene ring joined to Ir by a direct bond, then Y′ is not O and Y 2 is not CRR′;
wherein each R, R′, R A and R B is independently 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.