IP Library › Granted Patent US 11,744,142

Granted Patent B2

US 11,744,142 · App. 16/044,620 · Granted Aug 29, 2023

Organic electroluminescent materials and devices

Inventors: Geza Szigethy (Newtown, PA); Joseph A. Macor (Ewing, NJ); Charles Stanton (New Castle, DE); Galyna Dubinina (New Castle, DE); Douglas Williams (New Castle, DE)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/342 C07F15/0033 C09K11/06 H05B33/14 H10K85/40 H10K85/6572 C09K2211/1044 C09K2211/1055 C09K2211/1096 C09K2211/185 H10K50/11 H10K2101/10

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Quick Facts

Patent No.: US 11,744,142
App. No.: 16/044,620
Granted: Aug 29, 2023
Kind: B2

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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 (978)

1. A compound selected from the following structures G nk =Ir(Ligand 1)(Ligand 2)(Ligand 3) in the following table, wherein k is an integer having a value of 5 or 7:

G nk

Ligand 1

Ligand 2

Ligand 3

G n5

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

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

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:

wherein 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, hereroaryl, and combinations thereof; wherein any adjacent R A to R F are optionally joined or fused into 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 R 1 ;

wherein the carbon marked by * 2 connects to 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 1 , R 2 , R 3 , R 4 , and R 5 independently represents mono to a maximum possible 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 each of R 4 , R 5 , R G , R H , R 1 , and R 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 6, 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 16 to 41, are defined as follows:

L Bp

* 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 .

wherein L 1 or L 2 have a structure selected from the group consisting of

wherein R 10 ═CH 2 or CD 2 ; and

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

2. The compound of claim 1 , wherein the compound is a compound V 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=132((191((191(q−1)+z)−1)+v)−1)+x

wherein x is an integer from 1 to 132, y and z are each independently an integer from 133 to 189, 238 to 371, and q is an integer from 3 to 6; and

each of L x , L y and L z is one of the following structures L1 to L189, L238 to L371:

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 6 ═H, in L14, R 7 =m-CD 3 C 6 H 4 , and R 6 =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 8 ═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 8 =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 8 ═H, in L44, R 7 =D, and R 8 ═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 8 =CD 3 , in L58, R 7 =p-tol, and R 8 ═H,

in L59, R 7 =p-tol, and R 8 =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 y =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 s =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,

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 =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 ,

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 Link3 through Link6 defined below:

Link3 and Link4 having the structure

wherein in Link3, R 10 ═CH 2 , and in Link4, R 10 =CD 2 , Link5 and Link6 having the structure

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

wherein the dashed line represents the bonds connecting to the carbon marked by *on L y and L z .

3. The compound of claim 2 , where the compound is selected from the group consisting of: 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 ), and Ir(L 120 )(L 120 -L 146 -Link 4 ).

4. A formulation comprising the compound of claim 1 .

5. 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 selected from the following structures G nk =Ir(Ligand 1)(Ligand 2)(Ligand 3) in the following table, wherein k is an integer having a value of 5 or 7:

G nk

Ligand 1

Ligand 2

Ligand 3

G n5

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

integer from 16 to 26

G n7

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

integer from 27 to 41

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:

wherein 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 R 1 ;

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

wherein the carbon marked by * 3 connects to L1 or R 4 ;

wherein the carbon marked by * 4 connects to L2 or R 5 ;

wherein each of R 1 , R 2 , R 3 , 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 I , 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 6, 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

wherein the ligands L Bp , wherein p is an integer from 16 to 41, are defined as follows:

having a

L Bp

structure

* 3

* 4

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

wherein L1 or L2 have a structure selected from the group consisting of

wherein R 10 ═CH 2 or CD 2 , and

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

6. The OLED of claim 5 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

7. The OLED of claim 5 , 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.

8. The OLED of claim 5 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

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

an anode;

a cathode; and

G nk

Ligand 1

Ligand 2

Ligand 3

G n5

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

integer from 16 to 26

G n7

L Ai , wherein i = an

L Bp , wherein p = an

integer from 1 to 6

integer from 27 to 41

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:

wherein the dashed lines in A 1 to A 6 indicate the connecting bonds:

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 R 1 ;

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

wherein the carbon marked by * 3 connects to L1 or R 4 ;

wherein the carbon marked by * 4 connects to L2 or R 5 ;

wherein each of R 1 , R 2 , R 3 , R 4 , and R 5 independently represents mono to a maximum possible number of substitutions, or no substitution;

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 6, 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

wherein the ligands L Bp , wherein p is an integer from 16 to 41, are defined as follows:

having a

L Bp

structure

* 3

* 4

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

wherein L1 or L2 have a structure selected from the group consisting of

wherein R 10 ═CH 2 or CD 2 , and

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

10. The consumer product of claim 9 , 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.

Assignments (1)

NUNC PRO TUNC ASSIGNMENT Recorded Jul 25, 2018

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

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 046453/0060 →

Continuity (2)

Provisional Application 62543694 · Aug 10, 2017

Related Publication 20190051845A1 · Feb 14, 2019