IP Library › Patent Application 18357223

Patent Application

App. No. 18/357,223

ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

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App. No.: 18/357,223

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Abstract

A compound having a structure of the formula Ir(L A )(L B ), in which L A is a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand and L B is a monodentate, bidentate, tridentate, or tetradentate ligand, or not present, and where the total denticity of L A plus L B is 6, and L A includes at least one structure of Formula I: is disclosed as a useful phosphorescent emitter compound.

Claims (917)

1 . A compound having the formula Ir(L A )(L B );

wherein L A is a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;

wherein L B is a monodentate, bidentate, tridentate, or tetradentate ligand, or not present;

wherein the total denticity of L A plus L B is 6;

wherein L A comprises at least one structure of Formula I:

Formula I

wherein A is a linking group having two to three linking atoms, wherein the linking atoms are each independently selected from the group consisting of C, Si, O, S, N, B;

wherein R 2 and R 3 each independently represents mono to a maximum allowable number of substitutions, or no substitution;

wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein any two substituents may be joined or fused together to form a ring; and

wherein R 1 or R 3 can join to another ligand via a linking group to form a higher denticity ligand.

2 . The compound of claim 1 , wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3 . The compound of claim 1 , wherein the linking group A is independently selected from the group consisting of —CR A R B —CR C R D —, —CR A R B —CR C R D —CR E R F —, —CR A R B —NR C —, —CR A =CR B —CR C R D —, —O—SiR A R B —, —CR A R B —S—, —CR A R B —O—, and —C—SiR A R B —, wherein each R A to R F can be same or different, and are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof; and

wherein any adjacent R A to R F are optionally joined or fused into a 5-membered or 6-membered ring.

4 . The compound of claim 1 , wherein the linking group A is selected from the group consisting of:

and

wherein the dashed lines represent the connecting bonds.

5 . The compound of claim 1 , wherein L A comprises one structure of Formula I.

6 . The compound of claim 1 , wherein L A is a tetradentate ligand comprising two identical or two different structures of Formula I.

7 . The compound of claim 1 , wherein L A is a hexadentate ligand comprising three identical or three different structures of Formula I.

8 . The compound of claim 1 , wherein the compound is a compound according to formula Ir(L A ) n (L B ) m (Link);

wherein each L A and L B represents a bidentate ligand fragment;

wherein at least one of L A contains a fragment described by Formula I;

wherein n=1, 2, or 3;

wherein mn=0, 1, or 2;

wherein n+m=3; and

wherein Link is an organic linker further designated as L 1 or L 2 used to connect one or more of L A and/or L B to form tetradentate or hexadentate ligands.

9 . The compound of claim 8 , wherein L 1 and L 2 each independently comprising 6-20 carbon atoms.

10 . The compound of claim 8 , wherein L 1 and L 2 each independently comprising a 6-membered aromatic ring or a cycloalkyl ring.

11 . The compound of claim 8 , wherein the compound is selected from the following structures G nk =Ir(Ligand 1)(Ligand 2)(Ligand 3) in the following table, wherein k is an integer from 1 to 4, 6, and 8 to 16:

G nk

Ligand 1

Ligand 2

Ligand 3

G n1

L Ai , wherein i = an

integer from 1 to 6

integer from 7 to 12

G n2

L Ai , wherein i = an

integer from 7 to 12

G n3

L Ai , wherein i = an

integer from 1 to 6

integer from 13 to

G n4

L Ai , wherein i = an

integer from 13 to

G n5

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

integer from 16 to

G n6

L Ai , wherein i = an

L Bp , wherein p = an

integer from 7 to 12

integer from 16 to

G n7

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

integer from 27 to

G n8

L Ai , wherein i = an

L Bp , wherein p = an

integer from 13 to

integer from 27 to

G n9

L Ai , wherein i = an

L Bp , wherein p = an

integer from 7 to 12

integer from 16 to

G n10

L Ai , wherein i = an

L Bp , wherein p = an

integer from 13 to

integer from 27 to

G n11

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

integer from 7 to 12

integer from 16 to

G n12

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

integer from 13 to

integer from 27 to

G n13

L Bp , wherein p = an

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 15

integer from 7 to 12

integer from 16 to

G n14

L Bp , wherein p = an

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 15

integer from 13 to

integer from 27 to

G n15

L Bp . wherein p = an

L Ai , wherein i = an

integer from 1 to 15

integer from 7 to 12

G n16

L Bp , wherein p = an

L Ai , wherein i = an

integer from 1 to 15

integer from 13 to

wherein the ligands L Ai comprises the following structure:

wherein the dashed lines represent bonds to the iridium atom;

wherein A is a linking group selected from the group consisting of:

where the dashed lines in A 1 to A 6 indicate the connecting bonds;

wherein each R A to R F can be same or different, and are independently selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof, wherein any adjacent R A to R F are optionally joined or fused into a 5-membered or 6-membered ring;

wherein L Bp is selected from the group consisting of:

wherein C is an organic linker selected from the group consisting of:

wherein the dashed lines indicate the connecting bonds;

wherein the carbon marked by * 1 connects to L 1 or R 1 ;

wherein the carbon marked by * 2 connects to L 2 or R 3 ;

wherein the carbon marked by * 3 connects to L 1 or R 4 ;

wherein the carbon marked by * 4 connects to L 2 or R 5 ;

wherein each of R 4 and R 5 independently represents mono to a maximum possible number of substitutions, or no substitution;

wherein each of R 4 , R 5 , R G , R H , R 1 , and R J is independently selected from the group consisting of hydrogen, deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;

wherein R is selected from the group consisting of methyl, deuterated methyl, isopropyl, substituted phenyl, and substituted dibenzofuran;

wherein the ligands L Ai , wherein i is an integer from 1 to 18, are defined as follows:

L Ai

* 1

* 2

L A1

A 1

R 1

R 3

L A2

A 2

R 1

R 3

L A3

A 3

R 1

R 3

L A4

A 4

R 1

R 3

L A5

A 5

R 1

R 3

L A6

A 6

R 1

R 3

L A7

A 1

L 1

R 3

L A8

A 2

L 1

R 3

L A9

A 3

L 1

R 3

L A10

A 4

L 1

R 3

L A11

A 5

L 1

R 3

L A12

A 6

L 1

R 3

L A13

A 1

R 1

L 2

L A14

A 2

R 1

L 2

L A15

A 3

R 1

L 2

L A16

A 4

R 1

L 2

L A17

A 5

R 1

L 2

L A18

A 6

R 1

L 2 ;

wherein the ligands L Bp , wherein p is an integer from 1 to 41, are defined as follows:

having

L Bp

structure

* 3

* 4

L B1

C 1

R 4

R 5

L B2

C 2

R 4

R 5

L B3

C 3

R 4

R 5

L B4

—

R 4

R 5

L B5

—

R 4

R 5

L B6

C 1

R 4

R 5

L B7

C 2

R 4

R 5

L B8

C 3

R 4

R 5

L B9

C 1

R 4

R 5

L B10

C 2

R 4

R 5

L B11

C 3

R 4

R 5

L B12

C 1

—

R 5

L B13

C 2

—

R 5

L B14

C 3

—

R 5

L B15

—

R 5

L B16

C 1

L 1

R 5

L B17

C 2

L 1

R 5

L B18

C 3

L 1

R 5

L B19

—

L 1

R 5

L B20

—

L 1

R 5

L B21

C 1

L 1

R 5

L B22

C 2

L 1

R 5

L B23

C 3

L 1

R 5

L B24

C 1

L 1

R 5

L B25

C 2

L 1

R 5

L B26

C 3

L 1

R 5

L B27

C 1

R 4

L 2

L B28

C 2

R 4

L 2

L B29

C 3

R 4

L 2

L B30

—

R 4

L 2

L B31

—

R 4

L 2

L B32

C 1

R 4

L 2

L B33

C 2

R 4

L 2

L B34

C 3

R 4

L 2

L B35

C 1

R 4

L 2

L B36

C 2

R 4

L 2

L B37

C 3

R 4

L 2

L B38

C 1

—

L 2

L B39

C 2

—

L 2

L B40

C 3

—

L 2

L B41

—

L 2 .

12 . The compound of claim 8 , wherein the compound is a compound V having the formula Ir(L x )(L y -L z -Link q ) or a compound W having the formula Ir(L x -L y -L z -Link q );

wherein in compound V, L x is a bidentate ligand;

wherein (L y -L z -Link q ) is a tetradentate ligand formed by linking bindentate ligand L y and bidentate ligand L z with Link q ;

wherein V is an integer defined by V=371((478((478(q−1)+z)−1)+y)−1)+x;

wherein one of the following conditions (a)-(d) are true:

(a) wherein x is an integer from 1 to 132, y and z are each independently an integer from 1 to 371, and q is an integer from 1 to 8;

(b) wherein x is an integer from 1 to 132, y and z are each independently an integer from 372 to 478, and q is an integer from 9 to 21;

(c) wherein x is an integer from 133 to 371, y is an integer from 1 to 132, z is an integer from 1 to 371, and q is an integer from 1 to 8; and

(d) wherein x is an integer from 133 to 371, y is an integer from 440 to 478, z is an integer from 372 to 478, and q is an integer from 9 to 21; and

wherein in compound W, (L x -L y -L z -Link q ) is a hexadentate ligand formed by connecting bidentate L x , L y , and L z with a linker Link q ;

wherein W is an integer defined by W=478((478((478(q−1)+z)−1)+y)−1)+x,

wherein x is an integer from 1 and 132, and y and z are each independently an integer from 1 to 371, and q is an integer from 22 to 39; or

wherein x is an integer from 440 to 478, and y and z are each independently an integer from 372 to 478, and q is an integer from 40 to 53;

wherein in both the compound V and the compound W, each of L x , L y and L z is one of the following structures L1 to L478:

L1, L2, L3, L4, L5, L6, L7, L8, L9, L10, L11, L12, L13, L14, L15, L16, L17, L18, L19, L20, and L21 having the structure

wherein in L1, R 7 =H, and R 8 =H, in L2, R 7 =D, and R 8 =H,

in L3, R 7 =H, and R 8 =Me, in L4, R 7 =D, and R 8 =Me,

in L5, R 7 =H, and R 8 =CD 3 , in L6, R 7 =D, and R 8 =CD 3 ,

in L7, R 7 =Ph, and R 8 =H, in L8, R 7 =Ph, and R 8 =Me,

in L9, R 7 =Ph, and R 8 =CD 3 , in L10, R 7 =m-tol, and R 8 =H,

in L11, R 7 =m-tol, and R 8 =Me, in L12, R 7 =m-tol, and R 8 =CD 3 ,

in L13, R 7 =m-CD 3 C 6 H 4 , and R 8 =H, in L14, R 7 =m-CD 3 C 6 H 4 , and R 8 =Me,

in L15, R 7 =m-CD 3 C 6 H 4 , and R 8 =CD 3 , in L16, R 7 =p-tol, and R 8 =H,

in L17, R 7 =p-tol, and R 8 =Me, in L18, R 7 =p-tol, and R 8 =CD 3 ,

in L19, R 7 =p-CD 3 C 6 H 4 , and R 8 =H, in L20, R 7 =p-CD 3 C 6 H 4 , and R 8 =Me,

and in L21, R 7 =p-CD 3 C 6 H 4 , and R 8 =CD 3 ,

L22, L23, L24, L25, L26, L27, L28, L29, L30, L31, L32, L33, L34, L35, L36, L37, L38, L39, L40, L41, and L42 having the structure

wherein in L22, R 7 =H, and R 6 =H, in L23, R 7 =D, and R 8 =H,

in L24, R 7 =H, and R 8 =Me, in L25, R 7 =D, and R 8 =Me,

in L26, R 7 =H, and R 8 =CD 3 , in L27, R 7 =D, and R 8 =CD 3 ,

in L28, R 7 =Ph, and R 8 =H, in L29, R 7 =Ph, and R 8 =Me,

in L30, R 7 =Ph, and R 8 =CD 3 , in L31, R 7 =m-tol, and R 8 =H,

in L32, R 7 =m-tol, and R 8 =Me, in L33, R 7 =m-tol, and R 8 =CD 3 ,

in L34, R 7 =m-CD 3 C 6 H 4 , and R 8 =H, in L35, R 7 =m-CD 3 C 6 H 4 , and R 8 =Me,

in L36, R 7 =m-CD 3 C 6 H 4 , and R 8 =CD 3 , in L37, R 7 =p-tol, and R 8 =H,

in L38, R 7 =p-tol, and R 6 =Me, in L39, R 7 =p-tol, and R 8 =CD 3 ,

in L40, R 7 =p-CD 3 C 6 H 4 , and R 8 =H, in L41, R 7 =p-CD 3 C 6 H 4 , and R 8 =Me,

and in L42, R 7 =p-CD 3 C 6 H 4 , and R 8 =CD 3 ,

L43, L44, L45, L46, L47, L48, L49, L50, L51, L52, L53, L54, L55, L56, L57, L58, L59, L60, L61, L62, and L63 having the structure

wherein in L43, R 7 =H, and R 6 =H, in L44, R 7 =D, and R a =H,

in L45, R 7 =H, and R 8 =Me, in L46, R 7 =D, and R 8 =Me,

in L47, R 7 =H, and R 8 =CD 3 , in L48, R 7 =D, and R 8 =CD 3 ,

in L49, R 7 =Ph, and R 8 =H, in L50, R 7 =Ph, and R 8 =Me,

in L51, R 7 =Ph, and R 8 =CD 3 , in L52, R 7 =m-tol, and R 8 =H,

in L53, R 7 =m-tol, and R 8 =Me, in L54, R 7 =m-tol, and R 8 =CD 3 ,

in L55, R 7 =m-CD 3 C 6 H 4 , and R 8 =H, in L56, R 7 =m-CD 3 C 6 H 4 , and R 8 =Me,

in L57, R 7 =m-CD 3 C 6 H 4 , and R a =CD 3 , in L58, R 7 =p-tol, and R 8 =H,

in L59, R 7 =p-tol, and R 6 =Me, in L60, R 7 =p-tol, and R 8 =CD 3 ,

in L61, R 7 =p-CD 3 C 6 H 4 , and R 8 =H, in L62, R 7 =p-CD 3 C 6 H 4 , and R 8 =Me,

and in L63, R 7 =p-CD 3 C 6 H 4 , and R 8 =CD 3 ,

L64, L65, L66, L67, L68, L69, L70, L71, L72, L73, L74, L75, L76, L77, L78, L79, L80, L81, L82, L83, and L84 having the structure

wherein in L64, R 7 =H, and R 8 =H, in L65, R 7 =D, and R 8 =H,

in L66, R 7 =H, and R 8 =Me, in L67, R 7 =D, and R 8 =Me,

in L68, R 7 =H, and R 8 =CD 3 , in L69, R 7 =D, and R 8 =CD 3 ,

in L70, R 7 =Ph, and R 8 =H, in L71, R 7 =Ph, and R 8 =Me,

in L72, R 7 =Ph, and R 8 =CD 3 , in L73, R 7 =m-tol, and R 8 =H,

in L74, R 7 =m-tol, and R 8 =Me, in L75, R 7 =m-tol, and R 8 =CD 3 ,

in L76, R 7 =m-CD 3 C 6 H 4 , and R 8 =H, in L77, R 7 =m-CD 3 C 6 H 4 , and R 8 =Me,

in L78, R 7 =m-CD 3 C 6 H 4 , and R 8 =CD 3 , in L79, R 7 =p-tol, and R 8 =H,

in L80, R 7 =p-tol, and R 8 =Me, in L81, R 7 =p-tol, and R 8 =CD 3 ,

in L82, R 7 =p-CD 3 C 6 H 4 , and R 8 =H, in L83, R 7 =p-CD 3 C 6 H 4 , and R 8 =Me,

and in L84, R 7 =p-CD 3 C 6 H 4 , and R 8 =CD 3 ,

L85, L86, L87, L88, L89, L90, L91, L92, L93, L94, L95, L96, L97, L98, L99, L100, L101, and L102 having the structure

wherein in L85, R 7 =H, R 8 =H, and R 9 =Me, in L86, R 7 =H, R 8 =Me, and R 9 =Me,

in L87, R 7 =H, R 8 =CD 3 , and R 9 =Me, in L88, R 7 =Ph, R 8 =H, and R 9 =Me,

in L89, R 7 =Ph, R 8 =Me, and R 9 =Me, in L90, R 7 =Ph, R 8 =CD 3 , and R 9 =Me,

in L91, R 7 =H, R 8 =H, and R 9 = i Pr, in L92, R 7 =H, R 8 =Me, and R 9 = i Pr,

in L93, R 7 =H, R 8 =CD 3 , and R 9 = i Pr, in L94, R 7 =Ph, R 8 =H, and R 9 = i Pr,

in L95, R 7 =Ph, R 8 =Me, and R 9 = i Pr, in L96, R 7 =Ph, R 8 =CD 3 , and R 9 = i Pr,

in L97, R 7 =H, R 8 =H, and R 9 =Ph, in L98, R 7 =H, R 8 =Me, and R 9 =Ph,

in L99, R 7 =H, R 8 =CD 3 , and R 9 =Ph, in L100, R 7 =Ph, R 8 =H, and R 9 =Ph,

in L101, R 7 =Ph, R 8 =Me, and R 9 =Ph, and in L102, R 7 =Ph, R 8 =CD 3 , and R 9 =Ph,

L103, L104, L105, L106, L107, and L108 having the structure

wherein in L103, R 7 =H, and R 8 =H, in L104, R 7 =H, and R 8 =Me,

in L105, R 7 =H, and R 8 =CD 3 , in L106, R 7 =Ph, and R 8 =H,

in L107, R 7 =Ph, and R 8 =Me, and in L108, R 7 =Ph, and R 8 =CD 3 ,

L109, L110, L111, L112, L113, L114, L115, L116, L117, L118, L119, L120, L121, L122, L123, L124, L125, and L126 having the structure

wherein in L109, R 7 =H, R 8 =H, and R 9 =Me, in L110, R 7 =H, R 8 =Me, and R 9 =Me,

in L111, R 7 =H, R 8 =CD 3 , and R 9 =Me, in L112, R 7 =Ph, R 8 =H, and R 9 =Me,

in L113, R 7 =Ph, R 8 =Me, and R 9 =Me, in L114, R 7 =Ph, R 8 =CD 3 , and R 9 =Me,

in L115, R 7 =H, R 8 =H, and R 9 =CD 3 , in L116, R 7 =H, R 8 =Me, and R 9 =CD 3 ,

in L117, R 7 =H, R 8 =CD 3 , and R 9 =CD 3 , in L118, R 7 =Ph, R 8 =H, and R 9 =CD 3 ,

in L119, R 7 =Ph, R 8 =Me, and R 9 =CD 3 , in L120, R 7 =Ph, R 8 =CD 3 , and R 9 =CD 3 ,

in L121, R 7 =H, R 8 =H, and R 9 =Ph, in L122, R 7 =H, R 8 =Me, and R 9 =Ph,

in L123, R 7 =H, R 8 =CD 3 , and R 9 =Ph, in L124, R 7 =Ph, R 8 =H, and R 9 =Ph,

in L125, R 7 =Ph, R 8 =Me, and R 9 =Ph, and in L126, R 7 =Ph, R 8 =CD 3 , and R 9 =Ph,

L127, L128, L129, L130, L131, and L132 having the structure

wherein in L127, R 7 =H, and R 8 =H, in L128, R 7 =H, and R 8 =Me,

in L129, R 7 =H, and R 8 =CD 3 , in L130, R 7 =Ph, and R 8 =H,

in L131, R 7 =Ph, and R 8 =Me, and in L132, R 7 =Ph, and R 8 =CD 3 ,

L133, L134, L135, L136, L137, L138, L139, L140, L141, L142, L143, and L144 having the structure

wherein in L133, R 7 =H, and R 8 =H, in L134, R 7 =H, and R 8 =Ph,

in L135, R 7 =H, and R 8 =2,6-Me 2 -C 6 H 3 , in L136, R 7 =H, and R 8 =2,6-(CD 3 ) 2 -C 6 H 3 ,

in L137, R 7 =H, and R 8 =2,6-( i Bu) 2 -C 6 H 3 , in L138, R 7 =Ph, and R 8 =H,

in L139, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =H, and in L140, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =H,

in L141, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =Ph, and in L142, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =Ph,

in L143, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =2,6-Me 2 -C 6 H 3 ,

and in L144, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =2,6-(CD 3 ) 2 -C 6 H 3 ,

L145, L146, L147, L148, L149, L150, L151, L152, and L153 having the structure

wherein in L145, R 7 =H, and R 8 =H, in L146, R 7 =H, and R 8 =Ph,

in L147, R 7 =H, and R 8 =2,6-Me 2 -C 6 H 3 , in L148, R 7 =H, and R 8 =2,6-(CD 3 ) 2 -C 6 H 3 ,

in L149, R 7 =Ph, and R 8 =H, in L150, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =H,

in L151, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =H, and in L152, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =Ph,

and in L153, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =Ph,

L154, L155, L156, L157, L158, L159, L160, L161, and L162 having the structure

wherein in L154, R 7 =H, and R 8 =H, in L155, R 7 =H, and R 8 =Ph,

in L156, R 7 =H, and R 8 =2,6-Me 2 -C 6 H 3 , in L157, R 7 =H, and R 8 =2,6-(CD 3 ) 2 -C 6 H 3 ,

in L158, R 7 =Ph, and R 8 =H, in L159, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =H,

in L160, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =H, and in L161, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =Ph,

and in L162, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =Ph,

L163, L164, L165, L166, L167, L168, L169, L170, and L171 having the structure

wherein in L163, R 7 =H, and R 8 =H, in L164, R 7 =H, and R 8 =Ph,

in L165, R 7 =H, and R 8 =2,6-Me 2 -C 6 H 3 , in L166, R 7 =H, and R 8 =2,6-(CD 3 ) 2 -C 6 H 3 ,

in L167, R 7 =Ph, and R 8 =H, in L168, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =H,

in L169, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =H, and in L170, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =Ph,

and in L171, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =Ph,

L172, L173, L174, L175, L176, L177, L178, L179, and L180 having the structure

wherein in L172, R 7 =H, and R 8 =H, in L173, R 7 =H, and R 8 =Ph,

in L174, R 7 =H, and R 8 =2,6-Me 2 -C 6 H 3 , in L175, R 7 =H, and R 8 =2,6-(CD 3 ) 2 -C 6 H 3 ,

in L176, R 7 =Ph, and R 8 =H, in L177, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =H,

in L178, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =H, and in L179, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =Ph,

and in L180, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =Ph,

L181, L182, L183, L184, L185, L186, L187, L188, and L189 having the structure

wherein in L181, R 7 =H, and R 8 =H, in L182, R 7 =H, and R 8 =Ph,

in L183, R 7 =H, and R 8 =2,6-Me 2 -C 6 H 3 , in L184, R 7 =H, and R 8 =2,6-(CD 3 ) 2 -C 6 H 3 ,

in L185, R 7 =Ph, and R 8 =H, in L186, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =H,

in L187, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =H, and in L188, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =Ph,

and in L189, R 7 =3,5-(CD 3 ) 2 -C 6 H 3 , and R 8 =Ph,

L190, L191, L192, L193, L194, and L195 having the structure

wherein in L190, R 7 =Me, in L191, R 7 =CD 3 , in L192, R 7 = i Pr,

in L193, R 7 =Ph, in L194, R 7 =2,6-Me 2 -C 6 H 3 , and in L195, R 7 =3,5-Me 2 -C 6 H 3 ,

L196, L197, L198, L199, L200, and L201 having the structure

wherein in L196, R 7 =Me, in L197, R 7 =CD 3 , in L198, R 7 = i Pr,

in L199, R 7 =Ph, in L200, R 7 =2,6-Me 2 -C 6 H 3 , and in L201, R 7 =3,5-Me 2 -C 6 H 3 ,

L202, L203, L204, L205, L206, and L207 having the structure

wherein in L202, R 7 =Me, in L203, R 7 =CD 3 , in L204, R 7 = i Pr,

in L205, R 7 =Ph, in L206, R 7 =2,6-Me 2 -C 6 H 3 , and in L207, R 7 =3,5-Me 2 -C 6 H 3 ,

L208, L209, L210, L211, L212, and L213 having the structure

wherein in L208, R 7 =Me, in L209, R 7 =CD 3 , in L210, R 7 = i Pr,

in L211, R 7 =Ph, in L212, R 7 =2,6-Me 2 -C 6 H 3 , and in L213, R 7 =3,5-Me 2 -C 6 H 3 ,

L214, L215, L216, L217, L218, and L219 having the structure

wherein in L214, R 7 =Me, in L215, R 7 =CD 3 , in L216, R 7 = i Pr,

in L217, R 7 =Ph, in L218, R 7 =2,6-Me 2 -C 6 H 3 , and in L219, R 7 =3,5-Me 2 -C 6 H 3 ,

L220, L221, L222, L223, L224, and L225 having the structure

wherein in L220, R 7 =Me, in L221, R 7 =CD 3 , in L222, R 7 = i Pr,

in L223, R 7 =Ph, in L224, R 7 =2,6-Me 2 -C 6 H 3 , and in L225, R 7 =3,5-Me 2 -C 6 H 3 ,

L226, L227, L228, L229, L230, and L231 having the structure

wherein in L226, R 7 =Me, in L227, R 7 =CD 3 , in L228, R 7 = i Pr,

in L229, R 7 =Ph, in L230, R 7 =2,6-Me 2 -C 6 H 3 , and in L231, R 7 =3,5-Me 2 -C 6 H 3 ,

L232, L233, L234, L235, L236, and L237 having the structure

wherein in L232, R 7 =Me, in L233, R 7 =CD 3 , in L234, R 7 = i Pr,

in L235, R 7 =Ph, in L236, R 7 =2,6-Me 2 -C 6 H 3 , and in L237, R 7 =3,5-Me 2 -C 6 H 3 ,

L238, L239, L240, and L241 having the structure

wherein in L238, R 7 =Me, and R 8 =H, in L239, R 7 = i Pr, and R 8 =H,

in L240, R 7 =Me, and R 8 =Ph, and in L241, R 7 = i Pr, and R 8 =Ph,

L242, and L243 having the structure

wherein in L242, R 7 =Me, and R 8 =H, and in L243, R 7 =Me, and R 8 =Ph,

L244, and L245 having the structure

wherein in L244, R 7 =Me, and in L245, R 7 = i Pr,

L246 having the structure,

L247, L248, L249, and L250 having the structure

wherein in L247, R 7 =Me, and R 8 =H, in L248, R 7 = i Pr, and R 8 =H,

in L249, R 7 =Me, and R 8 =Ph, and in L250, R 7 = i Pr, and R 8 =Ph,

L250, and L251 having the structure

wherein in L250, R 7 =Me, and R 8 =H, and in L251, R 7 =Me, and R 8 =Ph,

L252, and L253 having the structure

wherein in L252, R 7 =Me, and in L253, R 7 = i Pr,

L255 having the structure

L256, L257, L258, L259, L260, L261, L262, L263, L264, L265, L266, L267, and L268 having the structure

wherein in L256, R 7 =H, and R 8 =Me, in L257, R 7 =H, and R 8 =CD 3 ,

in L258, R 7 =H, and R 8 = i Pr, in L259, R 7 =H, and R 8 =2,6-Me 2 -C 6 H 3 ,

in L260, R 7 =H, and R 8 =2,6- i Pr 2 -C 6 H 3 , in L261, R 7 =Me, and R 8 =2,6-Me 2 -C 6 H 3 ,

in L262, R 7 =Me, and R 8 =2,6- i Pr 2 -C 6 H 3 , in L263, R 7 =CD 3 , and R 8 =2,6-Me 2 -C 6 H 3 ,

in L264, R 7 =CD 3 , and R 8 =2,6- i Pr 2 -C 6 H 3 , in L265, R 7 =Ph, and R 8 =2,6-Me 2 -C 6 H 3 ,

in L266, R 7 =Ph, and R 8 =2,6- i Pr 2 -C 6 H 3 , in L267, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =2,6-Me 2 -C 6 H 3 , and in L268, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =2,6- i Pr 2 -C 6 H 3 ,

L269, L270, L271, L272, L273, L274, L275, L276, L277, L278, L279, L280, and L281 having the structure

wherein in L269, R 7 =H, and R 8 =Me, in L270, R 7 =H, and R 8 =CD 3 ,

in L271, R 7 =H, and R 8 = i Pr, in L272, R 7 =H, and R 8 =2,6-Me 2 -C 6 H 3 ,

in L273, R 7 =H, and R 8 =2,6- i Pr 2 -C 6 H 3 , in L274, R 7 =Me, and R 8 =2,6-Me 2 -C 6 H 3 ,

in L275, R 7 =Me, and R 8 =2,6- i Pr 2 -C 6 H 3 , in L276, R 7 =CD 3 , and R 8 =2,6-Me 2 -C 6 H 3 ,

in L277, R 7 =CD 3 , and R 8 =2,6- i Pr 2 -C 6 H 3 , in L278, R 7 =Ph, and R 8 =2,6-Me 2 -C 6 H 3 ,

in L279, R 7 =Ph, and R 8 =2,6- i Pr 2 -C 6 H 3 , in L280, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =2,6-Me 2 -C 6 H 3 ,

and in L281, R 7 =3,5-Me 2 -C 6 H 3 , and R 8 =2,6- i Pr 2 -C 6 H 3 ,

L282, L283, L284, and L285 having the structure

wherein in L282, R 7 =H, in L283, R 7 =Me,

in L284, R 7 =CD 3 , and in L285, R 7 =3,5-Me 2 -C 6 H 3 ,

L286, L287, L288, and L289 having the structure

wherein in L286, R 7 =H, in L287, R 7 =Me,

in L288, R 7 =CD 3 , and in L289, R 7 =3,5-Me 2 -C 6 H 3 ,

L290, L291, L292, and L293 having the structure

wherein in L290, R 7 =H, in L291, R 7 =Me,

in L292, R 7 =CD 3 , and in L293, R 7 =3,5-Me 2 -C 6 H 3 ,

L294, L295, L296, and L297 having the structure

wherein in L294, R 7 =H, in L295, R 7 =Me,

in L296, R 7 =CD 3 , and in L297, R 7 =3,5-Me 2 -C 6 H 3 ,

L298, L299, L300, and L301 having the structure

wherein in L298, R 7 =H, in L299, R 7 =Me,

in L300, R 7 =CD 3 , and in L301, R 7 =3,5-Me 2 -C 6 H 3 ,

L302, L303, L304, and L305 having the structure

wherein in L302, R 7 =H, in L303, R 7 =Me,

in L304, R 7 =CD 3 , and in L305, R 7 =3,5-Me 2 -C 6 H 3 ,

L306, L307, L308, and L309 having the structure

wherein in L306, R 7 =H, in L307, R 7 =Me,

in L308, R 7 =CD 3 , and in L309, R 7 =3,5-Me 2 -C 6 H 3 ,

L310, L311, L312, and L313 having the structure

wherein in L310, R 7 =H, in L311, R 7 =Me,

in L312, R 7 =CD 3 , and in L313, R 7 =3,5-Me 2 -C 6 H 3 ,

L314, L315, L316, and L317 having the structure

wherein in L314, R 7 =H, in L315, R 7 =Me,

in L316, R 7 =CD 3 , and in L317, R 7 =3,5-Me 2 -C 6 H 3 ,

L318, L319, L320, and L321 having the structure

wherein in L318, R 7 =Me, and R 8 =H, in L319, R 7 = i Pr, and R 8 =H,

in L320, R 7 =Me, and R 8 =Ph, and in L321, R 7 = i Pr, and R 8 =Ph,

L322, and L323 having the structure

wherein in L322, R 7 =Me, and R 8 =H, and in L323, R 7 = i Pr, and R 8 =H,

L324, and L325 having the structure

wherein in L324, R 7 =Me, and in L325, R 7 = i Pr,

L326 having the structure

L327, L328, L329, and L330 having the structure

wherein in L327, R 7 =Me, and R 8 =H, in L328, R 7 = i Pr, and R 8 =H,

in L329, R 7 =Me, and R 8 =Ph, and in L330, R 7 = i Pr, and R 8 =Ph,

L331, and L332 having the structure

wherein in L331, R 7 =Me, and R 8 =H, and in L332, R 7 =Me, and R 8 =Ph,

L333, and L334 having the structure

wherein in L333, R 7 =Me, and in L334, R 7 = i Pr,

L335 having the structure

L336, L337, L338, L339, L340, and L341 having the structure

wherein in L336, R 7 =H, in L337, R 7 =Me,

in L338, R 7 =CD 3 , in L339, R 7 =Ph,

in L340, R 7 =3,5-Me 2 -C 6 H 3 , and in L341, R 7 =3,5-(CD 3 ) 2 -C 6 H 3

L342, L343, L344, L345, L346, and L347 having the structure

wherein in L342, R 7 =H, in L343, R 7 =Me,

in L344, R 7 =CD 3 , in L345, R 7 =Ph,

in L346, R 7 =3,5-Me 2 -C 6 H 3 , and in L347, R 7 =3,5-(CD 3 ) 2 -C 6 H 3

L348, L349, L350, L351, L352, and L353 having the structure

wherein in L348, R 7 =H, in L349, R 7 =Me,

in L350, R 7 =CD 3 , in L351, R 7 =Ph,

in L352, R 7 =3,5-Me 2 -C 6 H 3 , and in L353, R 7 =3,5-(CD 3 ) 2 -C 6 H 3

L354, L355, L356, L357, L358, and L359 having the structure

wherein in L354, R 7 =H, in L355, R 7 =Me,

in L356, R 7 =CD 3 , in L357, R 7 =Ph,

in L358, R 7 =3,5-Me 2 -C 6 H 3 , and in L359, R 7 =3,5-(CD 3 ) 2 -C 6 H 3

L360, L361, L362, L363, L364, and L365 having the structure

wherein in L360, R 7 =H, in L361, R 7 =Me,

in L362, R 7 =CD 3 , in L363, R 7 =Ph,

in L364, R 7 =3,5-Me 2 -C 6 H 3 , and in L365, R 7 =3,5-(CD 3 ) 2 -C 6 H 3

L366, L367, L368, L369, L370, and L371 having the structure

wherein in L366, R 7 =H, in L367, R 7 =Me,

in L368, R 7 =CD 3 , in L369, R 7 =Ph,

in L370, R 7 =3,5-Me 2 -C 6 H 3 , and in L371, R 7 =3,5-(CD 3 ) 2 -C 6 H 3

L372, L373, L374, L375, and L376 having the structure

wherein in L372, R 7 =H, in L373, R 7 =Ph,

in L374, R 7 =2,6-Me 2 C 6 H 3 , in L375, R 7 =2,6-(CD 3 ) 2 C 6 H 3 ,

and in L376, R 7 =2,6-( i Bu) 2 C 6 H 3 ,

L377, L378, and L379 having the structure

wherein in L377, R 7 =H, in L378, R 7 =Ph,

and in L379, R 7 =2,6-Me 2 C 6 H 3 ,

L380, L381, L382, and L383 having the structure

wherein in L380, R 7 =H, in L381, R 7 =Ph,

in L382, R 7 =2,6-Me 2 C 6 H 3 , and in L383, R 7 =2,6-(CD 3 ) 2 C 6 H 3 ,

L384, L385, L386, and L387 having the structure

wherein in L384, R 7 =H, in L385, R 7 =Ph,

in L386, R 7 =2,6-Me 2 C 6 H 3 , and in L387, R 7 =2,6-(CD 3 ) 2 C 6 H 3 ,

L388, L389, L390, and L391 having the structure

wherein in L388, R 7 =H, in L389, R 7 =Ph,

in L390, R 7 =2,6-Me 2 C 6 H 3 , and in L391, R y =2,6-(CD 3 ) 2 C 6 H 3 ,

L392, L393, L394, and L395 having the structure

wherein in L392, R 7 =H, in L393, R 7 =Ph,

in L394, R 7 =2,6-Me 2 C 6 H 3 , and in L395, R 7 =2,6-(CD 3 ) 2 C 6 H 3 ,

L396 having the structure

L397, L398, and L399 having the structure

wherein in L397, E 1 =CH, and E 2 =CH,

in L398, E 1 =N, and E 2 =CH,

and in L399, E 1 =N, and E 2 =N,

L400 having the structure

L401, L402, and L403 having the structure

wherein in L401, E 1 =CH, and E 2 =CH,

in L402, E 1 =N, and E 2 =CH,

and in L403, E 1 =N, and E 2 =N,

L404, L405, L406, and L407 having the structure

wherein in L404, R 7 =Me, and R 8 =H,

in L405, R 7 = i Pr, and R 8 =H,

in L406, R 7 =Me, and R 8 =Ph,

and in L407, R 7 = i Pr, and R 8 =Ph,

L408, L409, and L410 having the structure

wherein in L408, R 7 =Me, and R 8 =H,

in L409, R 7 =Me, and R 8 =Ph,

and in L410, R 7 = i Pr, and R 8 =Ph,

L411, and L412 having the structure

wherein in L411, R 7 =Me, and in L412, R 7 = i Pr,

L413 having the structure

L414, L415, L416, L417, and L418 having the structure

wherein in L414, R 7 =Me, in L415, R 7 =CD 3 ,

in L416, R 7 = i Pr, in L417, R 7 =2,6-(CD 3 ) 2 C 6 H 3 ,

and in L418, R 7 =2,6-( i Pr) 2 C 6 H 3 ,

L419, L420, L421, L422, and L423 having the structure

wherein in L419, R 7 =Me, in L420, R 7 =CD 3 ,

in L421, R 7 = i Pr, in L422, R 7 =2,6-(CD 3 ) 2 C 6 H 3 ,

and in L423, R y =2,6-( i Pr) 2 C 6 H 3 ,

L424, L425, L426, and L427 having the structure

wherein in L424, R 7 =Me, and R 8 =H,

in L425, R 7 = i Pr, and R 8 =H,

in L426, R 7 =Me, and R 8 =Ph,

and in L427, R 7 = i Pr, and R 8 =Ph,

L428, L429, and L430 having the structure

wherein in L428, R 7 =Me, and R 8 =H,

in L429, R 7 =Me, and R 8 =Ph,

and in L430, R 7 = i Pr, and R 8 =Ph,

L431, and L432 having the structure

wherein in L431, R 7 =Me, and in L432, R 7 = i Pr,

L433 having the structure

L434 having the structure

L435, L436, L437, L438, and L439 having the structure

wherein in L435, R 7 =Me, and R 8 =Me,

in L436, R 7 =CD 3 , and R 8 =Me,

in L437, R 7 =CD 3 , and R 8 =CD 3 ,

in L438, R 7 =Et, and R 8 =Me,

and in L439, R 7 =CH 2 CF 3 , and R 8 =Me,

L440, L441, L442, L443, L444, L445, L446, L447, L448, L449, L450, and L451 having the structure

wherein in L440, R 7 =H, R 8 =Me, and R 9 =Me, in L441, R 7 =Me, R 8 =Me, and R 9 =Me,

in L442, R 7 =CD 3 , R 8 =Me, and R 9 =Me, in L443, R 7 =H, R 8 =CD 3 , and R 9 =Me,

in L444, R 7 =Me, R 8 =CD 3 , and R 9 =Me, in L445, R 7 =CD 3 , R 8 =CD 3 , and R 9 =Me,

in L446, R 7 =H, R 8 =Me, and R 9 =CD 3 , in L447, R 7 =Me, R 8 =Me, and R 9 =CD 3 ,

in L448, R 7 =CD 3 , R 8 =Me, and R 9 =CD 3 , in L449, R 7 =H, R 8 =CD 3 , and R 9 =CD 3 ,

in L450, R 7 =Me, R 8 =CD 3 , and R 9 =CD 3 , and in L451, R 7 =CD 3 , R 8 =CD 3 , and R 9 =CD 3 ,

L452, L453, and L454 having the structure

wherein in L452, R 7 =H, in L453, R 7 =Me,

and in L454, R 7 =CD 3 ,

L455, L456, L457, L458, L459, L460, L461, L462, and L463 having the structure

wherein in L455, R 7 =H, and R 8 =Me,

in L456, R 7 =Me, and R 8 =Me,

in L457, R 7 =CD 3 , and R 8 =Me,

in L458, R 7 =H, and R 8 = i Pr,

in L459, R 7 =Me, and R 8 = i Pr,

in L460, R 7 =CD 3 , and R 8 = i Pr,

in L461, R 7 =H, and R 8 =Ph,

in L462, R 7 =Me, and R 8 =Ph, and

in L463, R 7 =CD 3 , and R 8 =Ph,

L464, L465, and L466 having the structure

wherein in L464, R 7 =H,

in L465, R 7 =Me, and

in L466: R 7 =CD 3 ,

L467, L468, L469, L470, L471, L472, L473, L474, and L475 having the structure

wherein in L467, R 7 =H, and R 8 =Me,

in L468, R 7 =Me, and R 8 =Me,

in L469, R 7 =CD 3 , and R 8 =Me,

in L470, R 7 =H, and R 8 =CD 3 ,

in L471, R 7 =Me, and R 8 =CD 3 ,

in L472, R 7 =CD 3 , and R 8 =CD 3 ,

in L473, R 7 =H, and R 8 =Ph,

in L474, R 7 =Me, and R 8 =Ph, and

in L475, R 7 =CD 3 , and R 8 =Ph,

L476, L477, and L478 having the structure

wherein in L476, R 7 =H,

in L477, R 7 =Me, and

in L478, R 7 =CD 3 ;

wherein the dashed lines indicate bonds to the iridium atom;

wherein the carbon marked with * connects to an H atom for all L x structures or connects to Link q in L y and L z structures; and

wherein in compound V, Link q is one of the structures Link1 through Link21 defined below, and in compound W, Link q is one of the structures Link22 through Link53 defined below:

Link1 and Link 2 having the structure

wherein in Link1, R 10 =CH 2 , and in Link 2, R 10 =CH 2 CH 2 ,

Link 3 and Link 4 having the structure

wherein in Link 3, R 10 =CH 2 , and in Link4, R 10 =CD 2 , Link 5 and Link6 having the structure

wherein in Link5, R 10 =CH 2 , and in Link6, R 10 =CD 2 ,

Link9, Link10, Link11, Link12, Link13, Link14, Link15, Link16, and Link17 having the structure

wherein in Link9, R 10 =H, R 11 =CH 2 , and R 12 =CH 2 ,

in Link10, R 10 =Me, R 11 =CH 2 , and R 12 =CH 2 ,

in Link11, R 10 =CD 3 , R 11 =CH 2 , and R 12 =CH 2 ,

in Link12, R 10 =H, R 11 =CD 2 , and R 12 =CH 2 ,

in Link13, R 10 =Me, R 11 =CD 2 , and R 12 =CH 2 ,

in Link14, R 10 =CD 3 , R 11 =CD 2 , and R 12 =CH 2 ,

in Link15, R 10 =H, R 11 =CD 2 , and R 12 =CD 2 ,

in Link16, R 10 =Me, R 11 =CD 2 , and R 12 =CD 2 ,

in Link17, R 10 =CD 3 , R 11 =CD 2 , and R 12 =CD 2 ,

Link20 and Link21 having the structure

wherein in Link20, R 10 =CH 2 , and in Link21, R 10 =CH 2 CH 2 ,

Link22, Link23, Link24, Link25, Link26, Link27, Link28, Link29, Link30, Link31, Link32, and Link33 having the structure

wherein, in Link22, R 10 =CH 2 , and R 11 =R 12 =H,

in Link23, R 10 =CD 2 , and R 11 =R 12 =H,

in Link24, R 10 =CH 2 , and R 11 =R 12 =Me,

in Link25, R 10 =CD 2 , and R 11 =R 12 =Me,

in Link26, R 10 =CH 2 , R 11 =Me, and R 12 =H,

in Link27, R 10 =CD 2 , R 11 =Me, and R 12 =H,

in Link28, R 10 =CH 2 , R 11 =Et, and R 12 =H,

in Link29, R 10 =CD 2 , R 11 =Et, and R 12 =H,

in Link30, R 10 =CH 2 , R 11 =CH 2 CF 3 , and R 12 =H,

in Link31, R 10 =CD 2 , R 11 =CH 2 CF 3 , and R 12 =H,

in Link32, R 10 =CH 2 , R 11 = i Bu, and R 12 =H,

in Link33, R 10 =CD 2 , R 11 = i Bu, and R 12 =H,

in Link34, R 10 =CH 2 , R 11 =CH 2 (CH 3 ) 3 , and R 12 =H,

in Link35, R 10 =CD 2 , R 11 =CH 2 (CH 3 ) 3 , and R 12 =H,

in Link36, R 10 =CH 2 , R 11 =CH 2 CH(CH 3 )(CF 3 ), and R 12 =H,

in Link37, R 10 =CD 2 , R 11 =CH 2 CH(CH 3 )(CF 3 ), and R 12 =H,

Link40 and Link41 having the structure

wherein, in Link40, R 10 =Me, and in Link41, R 10 =Ph, Link42 and Link43 having the structure

wherein, in Link42, R 10 =CH 2 , and in Link43, R 10 =O, Link 44, Link 45, Link 46, and Link47 having the structure

wherein, in Link44, R 1 =CH 2 , and R 2 =Me,

in Link45, R 1 =CH 2 , and R 2 =Ph,

in Link46, R 1 =O, and R 2 =Me, and

in Link47, R 1 =O, and R 2 =Ph,

Link48, Link49, Link50, Link51, Link52, and Link53 having the structure

wherein, in Link48, E=C, R 10 =CH 2 , and R 11 =Me,

in Link49, E=C, R 10 =CH 2 , and R 11 =Ph,

in Link50, E=C, R 10 =CD 2 , and R 11 =Me,

in Link51, E=C, R 10 =CD 2 , and R 11 =Ph,

in Link52, E=Si, R 10 =CH 2 , and R 11 =Me, and

in Link53, E=Si, R 10 =CH 2 , and R 11 =Ph; wherein the dashed line represents the bonds connecting to the carbon marked by *on L x , L y , and L z .

13 . The compound of claim 12 , where the compound is selected from the group consisting of: Ir(L 51 -L 51 -L 51 -Link 22 ), Ir(L 51 -L 51 -L 146 -Link 22 ), Ir(L 51 -L 146 -L 146 -Link 22 ), Ir(L 51 -L 51 -L 51 -Link 23 ), Ir(L 51 -L 51 -L 146 -Link 23 ), Ir(L 51 -L 146 -L 146 -Link 23 ), Ir(L 9 -L 9 -L 9 -Link 22 ), Ir(L 9 -L 9 -L 146 -Link 22 ), Ir(L 9 -L 146 -L 146 -Link 22 ), Ir(L 9 -L 9 -L 9 -Link 23 ), Ir(L 9 -L 9 -L 146 -Link 23 ), Ir(L 9 -L 146 -L 146 -Link 23 ), Ir(L 47 -L 47 -L 47 -Link 22 ), Ir(L 47 -L 47 -L 146 -Link 22 ), Ir(L 47 -L 146 -L 146 -Link 22 ), Ir(L 47 -L 47 -L 47 -Link 23 ), Ir(L 47 -L 47 -L 146 -Link 23 ), Ir(L 47 -L 146 -L 146 -Link 23 ), Ir(L 5 -L 5 -L 5 -Link 22 ), Ir(L 5 -L 5 -L 146 -Link 22 ), Ir(L 5 -L 146 -L 146 -Link 22 ), Ir(L 5 -L 5 -L 5 -Link 23 ), Ir(L 5 -L 5 -L 146 -Link 23 ), Ir(L 5 -L 146 -L 146 -Link 23 ), Ir(L 1 -L 1 -L 1 -Link 22 ), Ir(L 1 -L 1 -L 146 -Link 22 ), Ir(L 1 -L 146 -L 146 -Link 22 ), Ir(L 1 -L 1 -L 1 -Link 23 ), Ir(L 1 -L 1 -L 146 -Link 23 ), Ir(L 1 -L 146 -L 146 -Link 23 ), Ir(L 43 -L 43 -L 43 -Link 22 ), Ir(L 43 -L 43 -L 146 -Link 22 ), Ir(L 43 -L 146 -L 146 -Link 22 ), Ir(L 43 -L 43 -L 43 -Link 23 ), Ir(L 43 -L 43 -L 146 -Link 23 ), Ir(L 43 -L 146 -L 146 -Link 23 ), Ir(L 117 -L 117 -L 117 -Link 22 ), Ir(L 117 -L 117 -L 146 -Link 22 ), Ir(L 117 -L 146 -L 146 -Link 22 ), Ir(L 117 -L 117 -L 117 -Link 23 ), Ir(L 117 -L 117 -L 146 -Link 23 ), Ir(L 117 -L 146 -L 146 -Link 23 ), Ir(L 120 -L 120 -L 120 -Link 22 ), Ir(L 120 -L 120 -L 146 -Link 22 ), Ir(L 120 -L 146 -L 146 -Link 22 ), Ir(L 120 -L 120 -L 120 -Link 23 ), Ir(L 120 -L 120 -L 146 -Link 23 ), Ir(L 120 -L 146 -L 146 -Link 23 ), Ir(L 9 )(L 146 -L 146 -Link 3 ), Ir(L 9 )(L 146 -L 146 -Link 4 ), Ir(L 51 )(L 146 -L 146 -Link 3 ), Ir(L 51 )(L 146 -L 146 -Link 4 ), Ir(L 47 )(L 146 -L 146 -Link 3 ), Ir(L 47 )(L 146 -L 146 -Link 4 ), Ir(L 5 )(L 146 -L 146 -Link 3 ), Ir(L 5 )(L 146 -L 146 -Link 4 ), Ir(L 1 )(L 146 -L 146 -Link 3 ), Ir(L 1 )(L 146 -L 146 -Link 4 ), Ir(L 43 )(L 146 -L 146 -Link 3 ), Ir(L 43 )(L 146 -L 146 -Link 4 ), Ir(L 117 )(L 146 -L 146 -Link 3 ), Ir(L 117 )(L 146 -L 146 -Link 4 ), Ir(L 120 )(L 146 -L 146 -Link 3 ), Ir(L 120 )(L 146 -L 146 -Link 4 ), Ir(L 9 )(L 9 -L 146 -Link 3 ), Ir(L 9 )(L 9 -L 146 -Link 4 ), Ir(L 51 )(L 51 -L 146 -Link 3 ), Ir(L 51 )(L 51 -L 146 -Link 4 ), Ir(L 47 )(L 47 -L 146 -Link 3 ), Ir(L 47 )(L 47 -L 146 -Link 4 ), Ir(L 5 )(L 5 -L 146 -Link 3 ), Ir(L 5 )(L 5 -L 146 -Link 4 ), Ir(L 1 )(L 1 -L 146 -Link 3 ), Ir(L 1 )(L 1 -L 146 -Link 4 ), Ir(L 43 )(L 43 -L 146 -Link 3 ), Ir(L 43 )(L 43 -L 146 -Link 4 ), Ir(L 117 )(L 117 -L 146 -Link 3 ), Ir(L 117 )(L 117 -L 146 -Link 4 ), Ir(L 120 )(L 120 -L 146 -Link 3 ), Ir(L 120 )(L 120 -L 146 -Link 4 ), Ir(L 146 )(L 9 -L 146 -Link 3 ), Ir(L 146 )(L 9 -L 146 -Link 4 ), Ir(L 146 )(L 51 -L 146 -Link 3 ), Ir(L 146 )(L 51 -L 146 -Link 4 ), Ir(L 146 )(L 47 -L 146 -Link 3 ), Ir(L 146 )(L 47 -L 146 -Link 4 ), Ir(L 146 )(L 5 -L 146 -Link 3 ), Ir(L 146 )(L 5 -L 146 -Link 4 ), Ir(L 146 )(L 1 -L 146 -Link 3 ), Ir(L 146 )(L 1 -L 146 -Link 4 ), Ir(L 146 )(L 43 -L 146 -Link 3 ), Ir(L 146 )(L 43 -L 146 -Link 4 ), Ir(L 146 )(L 117 -L 146 -Link 3 ), Ir(L 146 )(L 117 -L 146 -Link 4 ), Ir(L 146 )(L 120 -L 146 -Link 3 ), Ir(L 146 )(L 120 -L 146 -Link 4 ), Ir(L 146 )(L 9 -L 146 -Link 3 ), Ir(L 146 )(L 9 -L 146 -Link 4 ), Ir(L 146 )(L 9 -L 9 -Link 3 ), Ir(L 146 )(L 9 -L 9 -Link 4 ), Ir(L 146 )(L 51 -L 51 -Link 3 ), Ir(L 146 )(L 51 -L 51 -Link 4 ), Ir(L 146 )(L 47 -L 47 -Link 3 ), Ir(L 146 )(L 47 -L 47 -Link 4 ), Ir(L 146 )(L 5 -L 5 -Link 3 ), Ir(L 146 )(L 5 -L 5 -Link 4 ), Ir(L 146 )(L 1 -L 1 -Link 3 ), Ir(L 146 )(L 1 -L 1 -Link 4 ), Ir(L 146 )(L 43 -L 43 -Link 3 ), Ir(L 146 )(L 43 -L 43 -Link 4 ), Ir(L 146 )(L 117 -L 117 -Link 3 ), Ir(L 146 )(L 117 -L 117 -Link 4 ), Ir(L 146 )(L 120 -L 120 -Link 3 ), and Ir(L 146 )(L 120 -L 120 -Link 4 ).

14 . 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 having the formula Ir(L A )(L B );

wherein L A is a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;

wherein L B is a monodentate, bidentate, tridentate, or tetradentate ligand, or not present;

wherein the total denticity of L A plus L B is 6;

wherein L A comprises at least one structure of Formula I:

wherein A is a linking group having two to three linking atoms, wherein the linking atoms are each independently selected from the group consisting of C, Si, O, S, N, B;

wherein R 2 and R 3 each independently represents mono to a maximum allowable number of substitutions, or no substitution;

wherein any two substituents may be joined or fused together to form a ring; and

wherein R 1 or R 3 can join to another ligand via a linking group to form a higher denticity ligand.

15 . The OLED of claim 14 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

16 . The OLED of claim 14 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of metal complex, triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

17 . The OLED of claim 14 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

18 . A consumer product comprising an organic light-emitting device comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound having the formula Ir(L A )(L B );

wherein L A is a bidentate, tridentate, tetradentate, pentadentate, or hexadentate ligand;

wherein L B is a monodentate, bidentate, tridentate, or tetradentate ligand, or not present;

wherein the total denticity of L A plus L B is 6;

wherein L A comprises at least one structure of Formula I:

wherein A is a linking group having two to three linking atoms, wherein the linking atoms are each independently selected from the group consisting of C, Si, O, S, N, B;

wherein R 2 and R 3 each independently represents mono to a maximum allowable number of substitutions, or no substitution;

wherein any two substituents may be joined or fused together to form a ring; and

wherein R 1 or R 3 can join to another ligand via a linking group to form a higher denticity ligand.

19 . The consumer product of claim 18 , wherein the consumer product is one of a flat panel display, a curved display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a rollable display, a foldable display, a stretchable display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall comprising multiple displays tiled together, a theater or stadium screen, or a sign.

20 . A formulation comprising the compound of claim 1 .

Assignments (1)

NUNC PRO TUNC ASSIGNMENT Recorded Jul 24, 2023

From: SZIGETHY, GEZA; MACOR, JOSEPH A.; STANTON, CHARLES; DUBININA, GALYNA; WILLIAMS, DOUGLAS

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 064351/0988 →