IP Library › Granted Patent US 12,751,198

Granted Patent B2

US 12,751,198 · App. 17/657,417 · Granted Sep 29, 2026

Organic electroluminescent materials and devices

Inventors: Neil Palmer (Frenchtown, NJ); Wei-Chun Shih (Lawrenceville, NJ); George Fitzgerald (Lambertville, NJ); Joseph A. Macor (Morrisville, PA); Rasha Hamze (Philadelphia, PA); Pierre-Luc T. Boudreault (Pennington, NJ); Geza Szigethy (Newtown, PA)

Assignee: UNIVERSAL DISPLAY CORPORATION

H10K85/342 C07F15/0033 C09K11/06 C09K2211/107 C09K2211/185 H10K50/11 H10K2101/10

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Quick Facts

Patent No.: US 12,751,198
App. No.: 17/657,417
Granted: Sep 29, 2026
Kind: B2

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Abstract

Provided are compounds comprising ligands L A that are ligands of Pt and Ir complexes for OLED applications. Also provided are formulations comprising these compounds comprising ligands L A that are ligands of Pt and Ir complexes for OLED applications. Further provided are OLEDs and related consumer products that utilize these compounds comprising ligands L A that are ligands of Pt and Ir complexes for OLED applications.

Claims (4442)

1 . A compound comprising a ligand L A of Formula I:

wherein

ring A and ring B each independently represents a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

Z 1 , Z 2 , Z 3 and Z 4 are each independently C or N;

L is a direct bond or selected from the group consisting of O, S, NR″, CR′R″, SiR′R″, BR′, P(O)R, and BR′R″;

K 1 and K 2 are each independently selected from the group consisting of direct bond, O, and S;

R A represents mono to the maximum allowable substitution;

at least one of R A or R B comprises a structure of Formula II or Formula III:

the dashed lines of Formula II and Formula III indicate direct bond to ring A or ring B;

X is selected from the group consisting of BR′, C═O, C═S, C═NR′, CR′R″ and SiR′R″;

Y 1 and Y 2 are each independently selected from the group consisting of O, S, NR′, and BR′;

ring C is a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

R B and R C each independently represent mono to the maximum allowable substitution, or no substitution;

each R, R′, R″, R A , R B , and R C 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;

L A is coordinated to a metal M through the dashed lines of Formula I, forming a 5-membered or 6-membered chelate ring;

M is optionally coordinated to other ligands;

L A is optionally joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two of adjacent R, R′, R″, R A , R B , and R C can be joined or fused together to form a ring;

when Y 1 and Y 2 of Formula II are independently selected from the group consisting of O and NR′, X is not CR′R″; and

when one of ring A or ring B is a 5-membered ring and one of R A or R B comprises a structure of Formula II, then X is not CR′R″.

2 . The compound of claim 1 , wherein R, R′, R″, 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, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.

3 . The compound of claim 1 , wherein Formula II is selected from the group consisting of the following formulas:

4 . The compound of claim 1 , wherein Formula III is selected from the group consisting of the following formulas:

5 . The compound of claim 1 , wherein Formula III is selected from the group consisting of the following formulas:

6 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of the following ligands:

wherein R′″ has the same definition as R′ and R″ and Y 3 is selected from the group consisting of O, S, and NR″.

7 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of the following ligands:

Y 3 is selected from the group consisting of O, S, and NR″.

8 . The compound of claim 7 , wherein L B is selected from the group consisting of the following ligands: L B1 through L B546 with general numbering formula L Bk (k is an integer from 1 to 546):

9 . The compound of claim 1 , wherein the ligand L A is selected from the group consisting of the following ligands:

L A

Structure of L A

L A 1-(Ri)(Rj)(Rk)(Rl)(Rm), L A 1-(R1)(R1)(R1)(R1)(R1) to L A 1-(R86)(R86)(R86)(R86)(R86) having the structure

L A 2-(Ri)(Rk)(Rl)(Rm), L A 2-(R1)(R1)(R1)(R1) to L A 2-(R86)(R86)(R86)(R86) having the structure

L A 3-(Rj)(Rk)(Rl)(Rm), L A 3-(R1)(R1)(R1)(R1) to L A 3-(R86)(R86)(R86)(R86) having the structure

L A 4-(Rk)(Rl)(Rm), L A 4-(R1)(R1)(R1) to L A 4-(R86)(R86)(R86) having the structure

L A 5-(Ri)(Rj)(Rk)(Rl)(Rm), L A 5-(R1)(R1)(R1)(R1)(R1) to L A 5-(R86)(R86)(R86)(R86)(R86) having the structure

L A 6-(Ri)(Rk)(Rl)(Rm)(Rn) L A 6-(R1)(R1)(R1)(R1)(R1) to L A 6-(R86)(R86)(R86)(R86)(R86) having the structure

L A 7-(Rj)(Rk)(R)(Rm)(Rn), L A 7-(R1)(R1)(R1)(R1)(R1) to L A 7-(R86)(R86)(R86)(R86)(R86) having the structure

L A 8-(Rk)(Rl)(Rm)(Rn), L A 8-(R1)(R1)(R1)(R1) to L A 8-(R86)(R86)(R86)(R86) having the structure

L A 13-(Ri)(Rj)(Rk)(Rl)(Rm), L A 13-(R1)(R1)(R1)(R1)(R1) to L A 13-(R86)(R86)(R86)(R86)(R86) having the structure

L A 14-(Ri)(Rk)(Rl)(Rm), L A 14-(R1)(R1)(R1)(R1) to L A 14-(R86)(R86)(R86)(R86) having the structure

L A 15-(Rj)(Rk)(Rl)(Rm), L A 15-(R1)(R1)(R1)(R1) to L A 15-(R86)(R86)(R86)(R86) having the structure

L A 16-(Rk)(Rl)(Rm), L A 16-(R1)(R1)(R1) to L A 16-(R86)(R86)(R86) having the structure

L A 17-(Ri)(Rj)(Rk)(Rl)(Rm), L A 17-(R1)(R1)(R1)(R1)(R1)to L A 17-(R86)(R86)(R86)(R86)(R86) having the structure

L A 18-(Ri)(Rk)(Rl)(Rm)(Rn), L A 18-(R1)(R1)(R1)(R1)(R1) to L A 18-(R86)(R86)(R86)(R86)(R86) having the structure

L A 19-(Rj)(Rk)(Rl)(Rm)(Rn) L A 19-(R1)(R1)(R1)(R1)(R1) to L A 19-(R86)(R86)(R86)(R86)(R86) having the structure

L A 20-(Rk)(Rl)(Rm)(Rn), L A 20-(R1)(R1)(R1)(R1) to L A 20-(R86)(R86)(R86)(R86) having the structure

L A 25-(Ri)(Rj)(Rk)(Rm)(Rn), L A 25-(R1)(R1)(R1)(R1)(R1) to L A 25-(R86)(R86)(R86)(R86)(R86) having the structure

L A 26-(Ri)(Rj)(Rk)(Rm)(Rn), L A 26-(R1)(R1)(R1)(R1)(R1) to L A 26-(R86)(R86)(R86)(R86)(R86) having the structure

L A 27-(Ri)(Rj)(Rk)(Rl)(Rm), L A 27-(R1)(R1)(R1)(R1)(R1) to L A 27-(R86)(R86)(R86)(R86)(R86) having the structure

L A 28-(Ri)(Rj)(Rk)(R)(Rm), L A 28-(R1)(R1)(R1)(R1)(R1) to L A 28-(R86)(R86)(R86)(R86)(R86) having the structure

L A 29-(Ri)(Rj)(Rk)(Rl), L A 29-(R1)(R1)(R1)(R1) to L A 29-(R86)(R86)(R86)(R86) having the structure

L A 30-(Ri)(Rj)(Rk)(Rl), L A 30-(R1)(R1)(R1)(R1) to L A 30-(R86)(R86)(R86)(R86) having the structure

L A 31-(Ri)(Rj)(Rk)(Rl), L A 31-(R1)(R1)(R1)(R1) to L A 31-(R86)(R86)(R86)(R86) having the structure

L A 32-(Ri)(Rj)(Rk)(Rl), L A 32-(R1)(R1)(R1)(R1) to L A 32-(R86)(R86)(R86)(R86) having the structure

L A 33-(Ri)(Rj)(Rk)(Rl), L A 33-(R1)(R1)(R1)(R1) to L A 33-(R86)(R86)(R86)(R86) having the structure

L A 34-(Ri)(Rj)(Rk)(Rl), L A 34-(R1)(R1)(R1)(R1) to L A 34-(R86)(R86)(R86)(R86) having the structure

L A 35-(Ri)(Rj)(Rk)(Rl), L A 35-(R1)(R1)(R1)(R1) to L A 35-(R86)(R86)(R86)(R86) having the structure

L A 36-(Ri)(Rj)(Rk)(Rl), L A 36-(R1)(R1)(R1)(R1) to L A 36-(R86)(R86)(R86)(R86) having the structure

L A 37-(Ri)(Rj)(Rk)(Rl), L A 37-(R1)(R1)(R1)(R1) to L A 37-(R86)(R86)(R86)(R86) having the structure

L A 38-(Ri)(Rj)(Rk)(Rl), L A 38-(R1)(R1)(R1)(R1) to L A 38-(R86)(R86)(R86)(R86) having the structure

L A 39-(Ri)(Rj)(Rk)(Rl), L A 39-(R1)(R1)(R1)(R1) to L A 39-(R86)(R86)(R86)(R86) having the structure

L A 40-(Ri)(Rj)(Rk)(Rl), L A 40-(R1)(R1)(R1)(R1) to L A 40-(R86)(R86)(R86)(R86) having the structure

L A 41-(Ri)(Rj)(Rk)(Rl), L A 41-(R1)(R1)(R1)(R1) to L A 41-(R86)(R86)(R86)(R86) having the structure

L A 42-(Ri)(Rk)(Rl), L A 42-(R1)(R1)(R1) to L A 42-(R86)(R86)(R86) having the structure

L A 43-(Ri)(Rj)(Rk)(Rl), L A 43-(R1)(R1)(R1)(R1) to L A 43-(R86)(R86)(R86)(R86) having the structure

L A 44-(Ri)(Rj)(Rk)(Rl), L A 44-(R1)(R1)(R1)(R1) to L A 44-(R86)(R86)(R86)(R86) having the structure

L A 45-(Ri)(Rj)(Rk)(Rl), L A 45-(R1)(R1)(R1)(R1) to L A 45-(R86)(R86)(R86)(R86) having the structure

L A 46-(Ri)(Rj)(Rk)(Rl), L A 46-(R1)(R1)(R1)(R1) to L A 46-(R86)(R86)(R86)(R86) having the structure

L A 47-(Ri)(Rj)(Rk)(Rl)(Rm), L A 47-(R1)(R1)(R1)(R1)(R1) to L A 47-(R86)(R86)(R86)(R86)(R86) having the structure

L A 48-(Ri)(Rk)(Rl)(Rm), L A 48-(R1)(R1)(R1)(R1) to L A 48-(R86)(R86)(R86)(R86) having the structure

L A 49-(Ri)(Rj)(Rk)(Rl)(Rm), L A 49-(R1)(R1)(R1)(R1)(R1) to L A 49-(R86)(R86)(R86)(R86)(R86) having the structure

L A 50-(Ri)(Rj)(Rk)(Rl)(Rm), L A 50-(R1)(R1)(R1)(R1)(R1) to L A 50-(R86)(R86)(R86)(R86)(R86) having the structure

L A 51-(Ri)(Rj)(Rk)(Rl)(Rm), L A 51-(R1)(R1)(R1)(R1)(R1) to L A 51-(R86)(R86)(R86)(R86)(R86) having the structure

L A 52-(Ri)(Rj)(Rk)(Rl)(Rm), L A 52-(R1)(R1)(R1)(R1)(R1) to L A 52-(R86)(R86)(R86)(R86)(R86) having the structure

L A 53-(Ri)(Rj)(Rk)(Rl)(Rm), L A 53-(R1)(R1)(R1)(R1)(R1) to L A 53-(R86)(R86)(R86)(R86)(R86) having the structure

L A 54-(Ri)(Rj)(Rk)(Rl)(Rm), L A 54-(R1)(R1)(R1)(R1)(R1) to L A 54-(R86)(R86)(R86)(R86)(R86) having the structure

L A 55-(Ri)(Rj)(Rk)(Rm)(Rn), L A 55-(R1)(R1)(R1)(R1)(R1) to L A 55-(R86)(R86)(R86)(R86)(R86) having the structure

L A 56-(Ri)(Rj)(Rk)(Rm)(Rn), L A 56-(R1)(R1)(R1)(R1)(R1) to L A 56-(R86)(R86)(R86)(R86)(R86) having the structure

L A 57-(Ri)(Rj)(Rk)(Rl)(Rm), L A 57-(R1)(R1)(R1)(R1)(R1) to L A 57-(R86)(R86)(R86)(R86)(R86) having the structure

L A 58-(Ri)(Rj)(Rk)(R)(Rm), L A 58-(R1)(R1)(R1)(R1)(R1) to L A 58-(R86)(R86)(R86)(R86)(R86) having the structure

L A 59-(Ri)(Rj)(Rk)(Rl), L A 59-(R1)(R1)(R1)(R1) to L A 59-(R86)(R86)(R86)(R86) having the structure

L A 60-(Ri)(Rj)(Rk)(Rl), L A 60-(R1)(R1)(R1)(R1) to L A 60-(R86)(R86)(R86)(R86) having the structure

L A 61-(Ri)(Rj)(Rk)(Rl), L A 61-(R1)(R1)(R1)(R1) to L A 61-(R86)(R86)(R86)(R86) having the structure

L A 62-(Ri)(Rj)(Rk)(Rl), L A 62-(R1)(R1)(R1)(R1) to L A 62-(R86)(R86)(R86)(R86) having the structure

L A 63-(Ri)(Rj)(Rk)(Rl), L A 63-(R1)(R1)(R1)(R1) to L A 63-(R86)(R86)(R86)(R86) having the structure

L A 64-(Ri)(Rk)(Rl), L A 64-(R1)(R1)(R1) to L A 64-(R86)(R86)(R86) having the structure

L A 65-(Ri)(Rj)(Rk)(Rl), L A 65-(R1)(R1)(R1)(R1) to L A 65-(R86)(R86)(R86)(R86) having the structure

L A 66-(Ri)(Rk)(Rl)(Rm), L A 66-(R1)(R1)(R1)(R1) to L A 66-(R86)(R86)(R86)(R86) having the structure

L A 67-(Rk)(Rl)(Rm), L A 67-(R1)(R1)(R1) to L A 67-(R86)(R86)(R86) having the structure

L A 70-(Ri)(Rj)(Rk)(Rl), L A 70-(R1)(R1)(R1)(R1) to L A 70-(R86)(R86)(R86)(R86) having the structure

L A 71-(Ri)(Rj)(Rk)(Rl), L A 71-(R1)(R1)(R1)(R1) to L A 71-(R86)(R86)(R86)(R86) having the structure

L A 72-(Ri)(Rj)(Rk)(Rl), L A 72-(R1)(R1)(R1)(R1) to L A 72-(R86)(R86)(R86)(R86) having the structure

L A 73-(Ri)(Rj)(Rk)(Rl), L A 73-(R1)(R1)(R1)(R1) to L A 73-(R86)(R86)(R86)(R86) having the structure

L A 74-(Ri)(Rj)(Rk)(Rl), L A 74-(R1)(R1)(R1)(R1) to L A 74-(R86)(R86)(R86)(R86) having the structure

LA75-(Ri)(Rj)(Rk)(Rl), LA75-(R1)(R1)(R1)(R1) to LA75-(R86)(R86)(R86)(R86) having the structure

LA76-(Ri)(Rj)(Rk)(Rl), LA76-(R1)(R1)(R1)(R1) to LA76-(R86)(R86)(R86)(R86) having the structure

LA77-(Ri)(Rj)(Rk)(Rl), LA77-(R1)(R1)(R1)(R1) to LA77-(R86)(R86)(R86)(R86) having the structure

LA78-(Ri)(Rj)(Rk)(Rl), LA78-(R1)(R1)(R1)(R1) to LA78-(R86)(R86)(R86)(R86) having the structure

L A 79-(Ri)(Rj)(Rk)(Rl), L A 79-(R1)(R1)(R1)(R1) to L A 79-(R86)(R86)(R86)(R86) having the structure

L A 80-(Ri)(Rj)(Rk)(Rl), L A 80-(R1)(R1)(R1)(R1) to L A 80-(R86)(R86)(R86)(R86) having the structure

L A 81-(Ri)(Rj)(Rk)(Rl), L A 81-(R1)(R1)(R1)(R1) to L A 81-(R86)(R86)(R86)(R86) having the structure

L A 82-(Ri)(Rj)(Rk)(Rl), L A 82-(R1)(R1)(R1)(R1) to L A 82-(R86)(R86)(R86)(R86) having the structure

L A 83-(Ri)(Rj)(Rk)(Rl), L A 83-(R1)(R1)(R1)(R1) to L A 83-(R86)(R86)(R86)(R86) having the structure

L A 84-(Ri)(Rj)(Rk)(Rl), L A 84-(R1)(R1)(R1)(R1) to L A 84-(R86)(R86)(R86)(R86) having the structure

L A 85-(Ri)(Rj)(Rk)(Rl)(Rm), L A 85-(R1)(R1)(R1)(R1)(R1) to L A 85-(R86)(R86)(R86)(R86)(R86) having the structure

L A 86-(Ri)(Rj)(Rk)(Rl)(Rm), L A 86-(R1)(R1)(R1)(R1)(R1) to L A 86-(R86)(R86)(R86)(R86)(R86) having the structure

L A 87-(Ri)(Rj)(Rk)(Rl)(Rm), L A 87-(R1)(R1)(R1)(R1)(R1) to L A 87-(R86)(R86)(R86)(R86)(R86) having the structure

L A 88-(Ri)(Rj)(Rk)(Rl)(Rm), L A 88-(R1)(R1)(R1)(R1)(R1) to L A 88-(R86)(R86)(R86)(R86)(R86) having the structure

L A 89-(Ri)(Rj)(Rk)(Rl)(Rm), L A 89-(R1)(R1)(R1)(R1)(R1) to L A 89-(R86)(R86)(R86)(R86)(R86) having the structure

L A 90-(Ri)(Rk)(Rl)(Rm), L A 90-(R1)(R1)(R1)(R1) to L A 90-(R86)(R86)(R86)(R86) having the structure

L A 91-(Ri)(Rj)(Rk)(Rl)(Rm), L A 91-(R1)(R1)(R1)(R1)(R1) to L A 91-(R86)(R86)(R86)(R86)(R86) having the structure

L A 92-(Ri)(Rk)(Rl)(Rm)(Rn), L A 92-(R1)(R1)(R1)(R1)(R1) to L A 92-(R86)(R86)(R86)(R86)(R86) having the structure

L A 93-(Rk)(Rl)(Rm)(Rn), L A 93-(R1)(R1)(R1)(R1) to L A 93-(R86)(R86)(R86)(R86) having the structure

L A 96-(Ri)(Rj)(Rk)(Rl)(Rm), L A 96-(R1)(R1)(R1)(R1)(R1) to L A 96-(R86)(R86)(R86)(R86)(R86) having the structure

wherein Ri, Rj, Rk, Rl, Rm, and Rn are each independently selected from the list below:

10 . 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.

11 . The compound of claim 10 , wherein L B and L C are each independently selected from the group consisting of the following ligands:

wherein: T is selected from the group consisting of B, Al, Ga, and In; 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, S═O, SO 2 , 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, boryl, germyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, selenyl, and combinations thereof; 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 10 , wherein each L c is selected from the group consisting of the following ligands:

L Cj-I and L Cj-II ; wherein L Cj-I has a structure based on formula

and L Cj-II has a structure based on formula

wherein i is an integer from 1 to 1416; and

wherein for each L Cj in L Cj-I and L Cj-II , R 201 and R 202 are each independently defined as follows:

L Cj

R 201

R 202

L C1

R D1

L C2

R D2

L C3

R D3

L C4

R D4

L C5

R D5

L C6

R D6

L C7

R D7

L C8

R D8

L C9

R D9

L C10

R D10

L C11

R D11

L C12

R D12

L C13

R D13

L C14

R D14

L C15

R D15

L C16

R D16

L C17

R D17

L C15

R D18

L C19

R D19

L C20

R D20

L C21

R D21

L C22

R D22

L C23

R D23

L C24

R D24

L C25

R D25

L C26

R D26

L C27

R D27

L C28

R D28

L C29

R D29

L C30

R D30

L C31

R D31

L C32

R D32

L C33

R D33

L C34

R D34

L C35

R D35

L C36

R D36

L C37

R D37

L C38

R D38

L C39

R D39

L C40

R D40

L C41

R D41

L C42

R D42

L C43

R D43

L C44

R D44

L C45

R D45

L C46

R D46

L C47

R D47

L C48

R D48

L C49

R D49

L C50

R D50

L C51

R D51

L C52

R D52

L C53

R D53

L C54

R D54

L C55

R D55

L C56

R D56

L C57

R D57

L C58

R D58

L C59

R D59

L C60

R D60

L C61

R D61

L C62

R D62

L C63

R D63

L C64

R D64

L C65

R D65

L C66

R D66

L C67

R D67

L C68

R D68

L C69

R D69

L C70

R D70

L C71

R D71

L C72

R D72

L C73

R D73

L C74

R D74

L C75

R D75

L C76

R D76

L C77

R D77

L C78

R D78

L C79

R D79

L C80

R D80

L C81

R D81

L C82

R D82

L C83

R D83

L C84

R D84

L C85

R D85

L C86

R D86

L C87

R D87

L C88

R D88

L C89

R D89

L C90

R D90

L C91

R D91

L C92

R D92

L C93

R D93

L C94

R D94

L C95

R D95

L C96

R D96

L C97

R D97

L C98

R D98

L C99

R D99

L C100

R D100

L C101

R D101

L C102

R D102

L C103

R D103

L C104

R D104

L C105

R D105

L C106

R D106

L C107

R D107

L C108

R D108

L C109

R D109

L C110

R D10

R D110

L C111

R D111

L C112

R D112

L C113

R D113

L C114

R D114

L C115

R D115

L C116

R D116

L C117

R D117

L C118

R D118

L C119

R D119

L C120

R D120

L C121

R D121

L C122

R D122

L C123

R D123

L C124

R D124

L C125

R D125

L C126

R D126

L C127

R D127

L C128

R D128

L C129

R D129

L C130

R D130

L C131

R D131

L C132

R D132

L C133

R D133

L C134

R D134

L C135

R D135

L C136

R D136

L C137

R D137

L C138

R D138

L C139

R D139

L C140

R D140

L C141

R D141

L C142

R D142

L C143

R D143

L C144

R D144

L C145

R D145

L C146

R D146

L C147

R D147

L C148

R D148

L C149

R D149

L C150

R D150

L C151

R D151

L C152

R D152

L C153

R D153

L C154

R D154

L C155

R D155

L C156

R D156

L C157

R D157

L C158

R D158

L C159

R D159

L C160

R D160

L C161

R D161

L C162

R D162

L C163

R D163

L C164

R D164

L C165

R D165

L C166

R D166

L C167

R D167

L C168

R D168

L C169

R D169

L C170

R D170

L C171

R D171

L C172

R D172

L C173

R D173

L C174

R D174

L C175

R D175

L C176

R D176

L C177

R D177

L C178

R D178

L C179

R D179

L C180

R D180

L C181

R D181

L C182

R D182

L C183

R D183

L C184

R D184

L C185

R D185

L C186

R D186

L C187

R D187

L C188

R D188

L C189

R D189

L C190

R D190

L C191

R D191

L C192

R D192

L C193

R D1

R D3

L C194

R D1

R D4

L C195

R D1

R D5

L C196

R D1

R D9

L C197

R D1

R D10

L C198

R D1

R D17

L C199

R D1

R D18

L C200

R D1

R D20

L C201

R D1

R D22

L C202

R D1

R D37

L C203

R D1

R D40

L C204

R D1

R D41

L C205

R D1

R D42

L C206

R D1

R D43

L C207

R D1

R D48

L C208

R D1

R D49

L C209

R D1

R D50

L C210

R D1

R D54

L C211

R D1

R D55

L C212

R D1

R D58

L C213

R D1

R D59

L C214

R D1

R D78

L C215

R D1

R D79

L C216

R D1

R D81

L C217

R D1

R D87

L C218

R D1

R D88

L C219

R D1

R D89

L C220

R D1

R D93

L C221

R D1

R D116

L C222

R D1

R D117

L C223

R D1

R D118

L C224

R D1

R D119

L C225

R D1

R D120

L C226

R D1

R D133

L C227

R D1

R D134

L C228

R D1

R D135

L C229

R D1

R D136

L C230

R D1

R D143

L C231

R D1

R D144

L C232

R D1

R D145

L C233

R D1

R D146

L C234

R D1

R D147

L C235

R D1

R D149

L C236

R D1

R D151

L C237

R D1

R D154

L C238

R D1

R D155

L C239

R D1

R D161

L C240

R D1

R D175

L C241

R D4

R D3

L C242

R D4

R D5

L C243

R D4

R D9

L C244

R D4

R D10

L C245

R D4

R D17

L C246

R D4

R D18

L C247

R D4

R D20

L C248

R D4

R D22

L C249

R D4

R D37

L C250

R D4

R D40

L C251

R D4

R D41

L C252

R D4

R D42

L C253

R D4

R D43

L C254

R D4

R D48

L C255

R D4

R D49

L C256

R D4

R D50

L C257

R D4

R D54

L C258

R D4

R D55

L C259

R D4

R D58

L C260

R D4

R D59

L C261

R D4

R D78

L C262

R D4

R D79

L C263

R D4

R D81

L C264

R D4

R D87

L C265

R D4

R D88

L C266

R D4

R D89

L C267

R D4

R D93

L C268

R D4

R D116

L C269

R D4

R D117

L C270

R D4

R D118

L C271

R D4

R D119

L C272

R D4

R D120

L C273

R D4

R D133

L C274

R D4

R D134

L C275

R D4

R D135

L C276

R D4

R D136

L C277

R D4

R D143

L C278

R D4

R D144

L C279

R D4

R D145

L C280

R D4

R D146

L C281

R D4

R D147

L C282

R D4

R D149

L C283

R D4

R D151

L C284

R D4

R D154

L C285

R D4

R D155

L C286

R D4

R D161

L C287

R D4

R D175

L C288

R D9

R D3

L C289

R D9

R D5

L C290

R D9

R D10

L C291

R D9

R D17

L C292

R D9

R D18

L C293

R D9

R D20

L C294

R D9

R D22

L C295

R D9

R D37

L C296

R D9

R D40

L C297

R D9

R D41

L C298

R D9

R D42

L C299

R D9

R D43

L C300

R D9

R D48

L C301

R D9

R D49

L C302

R D9

R D50

L C303

R D9

R D54

L C304

R D9

R D55

L C305

R D9

R D58

L C306

R D9

R D59

L C307

R D9

R D78

L C308

R D9

R D79

L C309

R D9

R D81

L C310

R D9

R D87

L C311

R D9

R D88

L C312

R D9

R D89

L C313

R D9

R D93

L C314

R D9

R D116

L C315

R D9

R D117

L C316

R D9

R D118

L C317

R D9

R D119

L C318

R D9

R D120

L C319

R D9

R D133

L C320

R D9

R D134

L C321

R D9

R D135

L C322

R D9

R D136

L C323

R D9

R D143

L C324

R D9

R D144

L C325

R D9

R D145

L C326

R D9

R D146

L C327

R D9

R D147

L C328

R D9

R D149

L C329

R D9

R D151

L C330

R D9

R D154

L C331

R D9

R D155

L C332

R D9

R D161

L C333

R D9

R D175

L C334

R D10

R D3

L C335

R D10

R D5

L C336

R D10

R D17

L C337

R D10

R D18

L C338

R D10

R D20

L C339

R D10

R D22

L C340

R D10

R D37

L C341

R D10

R D40

L C342

R D10

R D41

L C343

R D10

R D42

L C344

R D10

R D43

L C345

R D10

R D48

L C346

R D10

R D49

L C347

R D10

R D50

L C348

R D10

R D54

L C349

R D10

R D55

L C350

R D10

R D58

L C351

R D10

R D59

L C352

R D10

R D78

L C353

R D10

R D79

L C354

R D10

R D81

L C355

R D10

R D87

L C356

R D10

R D88

L C357

R D10

R D89

L C358

R D10

R D93

L C359

R D10

R D116

L C360

R D10

R D117

L C361

R D10

R D118

L C362

R D10

R D119

L C363

R D10

R D120

L C364

R D10

R D133

L C365

R D10

R D134

L C366

R D10

R D135

L C367

R D10

R D136

L C368

R D10

R D143

L C369

R D10

R D144

L C370

R D10

R D145

L C371

R D10

R D146

L C372

R D10

R D147

L C373

R D10

R D149

L C374

R D10

R D151

L C375

R D10

R D154

L C376

R D10

R D155

L C377

R D10

R D161

L C378

R D10

R D175

L C379

R D17

R D3

L C380

R D17

R D5

L C381

R D17

R D18

L C382

R D17

R D20

L C383

R D17

R D22

L C384

R D17

R D37

L C385

R D17

R D40

L C386

R D17

R D41

L C387

R D17

R D42

L C388

R D17

R D43

L C389

R D17

R D48

L C390

R D17

R D49

L C391

R D17

R D50

L C392

R D17

R D54

L C393

R D17

R D55

L C394

R D17

R D58

L C395

R D17

R D59

L C396

R D17

R D78

L C397

R D17

R D79

L C398

R D17

R D81

L C399

R D17

R D87

L C400

R D17

R D88

L C401

R D17

R D89

L C402

R D17

R D93

L C403

R D17

R D116

L C404

R D17

R D117

L C405

R D17

R D118

L C406

R D17

R D119

L C407

R D17

R D120

L C408

R D17

R D133

L C409

R D17

R D134

L C410

R D17

R D135

L C411

R D17

R D136

L C412

R D17

R D143

L C413

R D17

R D144

L C414

R D17

R D145

L C415

R D17

R D146

L C416

R D17

R D147

L C417

R D17

R D149

L C418

R D17

R D151

L C419

R D17

R D154

L C420

R D17

R D155

L C421

R D17

R D161

L C422

R D17

R D175

L C423

R D50

R D3

L C424

R D50

R D5

L C425

R D50

R D18

L C426

R D50

R D20

L C427

R D50

R D22

L C428

R D50

R D37

L C429

R D50

R D40

L C430

R D50

R D41

L C431

R D50

R D42

L C432

R D50

R D43

L C433

R D50

R D48

L C434

R D50

R D49

L C435

R D50

R D54

L C436

R D50

R D55

L C437

R D50

R D58

L C438

R D50

R D59

L C439

R D50

R D78

L C440

R D50

R D79

L C441

R D50

R D81

L C442

R D50

R D87

L C443

R D50

R D88

L C444

R D50

R D89

L C445

R D50

R D93

L C446

R D50

R D116

L C447

R D50

R D117

L C448

R D50

R D118

L C449

R D50

R D119

L C450

R D50

R D120

L C451

R D50

R D133

L C452

R D50

R D134

L C453

R D50

R D135

L C454

R D50

R D136

L C455

R D50

R D143

L C456

R D50

R D144

L C457

R D50

R D145

L C458

R D50

R D146

L C459

R D50

R D147

L C460

R D50

R D149

L C461

R D50

R D151

L C462

R D50

R D154

L C463

R D50

R D155

L C464

R D50

R D161

L C465

R D50

R D175

L C466

R D55

R D3

L C467

R D55

R D5

L C468

R D55

R D18

L C469

R D55

R D20

L C470

R D55

R D22

L C471

R D55

R D37

L C472

R D55

R D40

L C473

R D55

R D41

L C474

R D55

R D42

L C475

R D55

R D43

L C476

R D55

R D45

L C477

R D55

R D49

L C478

R D55

R D54

L C479

R D55

R D58

L C480

R D55

R D59

L C481

R D55

R D78

L C482

R D55

R D79

L C483

R D55

R D81

L C484

R D55

R D87

L C485

R D55

R D88

L C486

R D55

R D89

L C487

R D55

R D93

L C488

R D55

R D116

L C489

R D55

R D117

L C490

R D55

R D118

L C491

R D55

R D119

L C492

R D55

R D120

L C493

R D55

R D133

L C494

R D55

R D134

L C495

R D55

R D135

L C496

R D55

R D136

L C497

R D55

R D143

L C498

R D55

R D144

L C499

R D55

R D145

L C500

R D55

R D146

L C501

R D55

R D147

L C502

R D55

R D149

L C503

R D55

R D151

L C504

R D55

R D154

L C505

R D55

R D155

L C506

R D55

R D161

L C507

R D55

R D175

L C508

R D116

R D3

L C509

R D116

R D5

L C510

R D116

R D17

L C511

R D116

R D18

L C512

R D116

R D20

L C513

R D116

R D22

L C514

R D116

R D37

L C515

R D116

R D40

L C516

R D116

R D41

L C517

R D116

R D42

L C518

R D116

R D43

L C519

R D116

R D48

L C520

R D116

R D49

L C521

R D116

R D54

L C522

R D116

R D58

L C523

R D116

R D59

L C524

R D116

R D78

L C525

R D116

R D79

L C526

R D116

R D51

L C527

R D116

R D87

L C528

R D116

R D88

L C529

R D116

R D89

L C530

R D116

R D93

L C531

R D116

R D117

L C532

R D116

R D118

L C533

R D116

R D119

L C534

R D116

R D120

L C535

R D116

R D133

L C536

R D116

R D134

L C537

R D116

R D135

L C538

R D116

R D136

L C539

R D116

R D143

L C540

R D116

R D144

L C541

R D116

R D145

L C542

R D116

R D146

L C543

R D116

R D147

L C544

R D116

R D149

L C545

R D116

R D151

L C546

R D116

R D154

L C547

R D116

R D155

L C548

R D116

R D161

L C549

R D116

R D175

L C550

R D143

R D3

L C551

R D143

R D5

L C552

R D143

R D17

L C553

R D143

R D18

L C554

R D143

R D20

L C555

R D143

R D22

L C556

R D143

R D37

L C557

R D143

R D40

L C558

R D143

R D41

L C559

R D143

R D42

L C560

R D143

R D43

L C561

R D143

R D48

L C562

R D143

R D49

L C563

R D143

R D54

L C564

R D143

R D58

L C565

R D143

R D59

L C566

R D143

R D78

L C567

R D143

R D79

L C568

R D143

R D81

L C569

R D143

R D87

L C570

R D143

R D88

L C571

R D143

R D89

L C572

R D143

R D93

L C573

R D143

R D116

L C574

R D143

R D117

L C575

R D143

R D118

L C576

R D143

R D119

L C577

R D143

R D120

L C578

R D143

R D133

L C579

R D143

R D134

L C580

R D143

R D135

L C581

R D143

R D136

L C582

R D143

R D144

L C583

R D143

R D145

L C584

R D143

R D146

L C585

R D143

R D147

L C586

R D143

R D149

L C587

R D143

R D151

L C588

R D143

R D154

L C589

R D143

R D155

L C590

R D143

R D161

L C591

R D143

R D175

L C592

R D144

R D3

L C593

R D144

R D5

L C594

R D144

R D17

L C595

R D144

R D18

L C596

R D144

R D20

L C597

R D144

R D22

L C598

R D144

R D37

L C599

R D144

R D40

L C600

R D144

R D41

L C601

R D144

R D42

L C602

R D144

R D43

L C603

R D144

R D48

L C604

R D144

R D49

L C605

R D144

R D54

L C606

R D144

R D58

L C607

R D144

R D59

L C608

R D144

R D78

L C609

R D144

R D79

L C610

R D144

R D81

L C611

R D144

R D87

L C612

R D144

R D88

L C613

R D144

R D89

L C614

R D144

R D93

L C615

R D144

R D116

L C116

R D144

R D117

L C617

R D144

R D118

L C618

R D144

R D119

L C619

R D144

R D120

L C620

R D144

R D133

L C621

R D144

R D134

L C622

R D144

R D135

L C623

R D144

R D136

L C624

R D144

R D145

L C625

R D144

R D146

L C626

R D144

R D147

L C627

R D144

R D149

L C628

R D144

R D151

L C629

R D144

R D154

L C630

R D144

R D155

L C631

R D144

R D161

L C632

R D144

R D175

L C633

R D145

R D3

L C634

R D145

R D5

L C635

R D145

R D17

L C636

R D145

R D18

L C637

R D145

R D20

L C638

R D145

R D22

L C639

R D145

R D37

L C640

R D145

R D40

L C641

R D145

R D41

L C642

R D145

R D42

L C643

R D145

R D43

L C644

R D145

R D48

L C645

R D145

R D49

L C646

R D145

R D54

L C647

R D145

R D58

L C648

R D145

R D59

L C649

R D145

R D78

L C650

R D145

R D79

L C651

R D145

R D81

L C652

R D145

R D87

L C653

R D145

R D88

L C654

R D145

R D89

L C655

R D145

R D93

L C656

R D145

R D116

L C657

R D145

R D117

L C658

R D145

R D118

L C659

R D145

R D119

L C660

R D145

R D120

L C661

R D145

R D133

L C662

R D145

R D134

L C663

R D145

R D135

L C664

R D145

R D136

L C665

R D145

R D146

L C666

R D145

R D147

L C667

R D145

R D149

L C668

R D145

R D151

L C669

R D145

R D154

L C670

R D145

R D155

L C671

R D145

R D161

L C672

R D145

R D175

L C673

R D146

R D3

L C674

R D146

R D5

L C675

R D146

R D17

L C676

R D146

R D18

L C677

R D146

R D20

L C678

R D146

R D22

L C679

R D146

R D37

L C680

R D146

R D40

L C681

R D146

R D41

L C682

R D146

R D42

L C683

R D146

R D43

L C684

R D146

R D48

L C685

R D146

R D49

L C686

R D146

R D54

L C687

R D146

R D58

L C688

R D146

R D59

L C689

R D146

R D78

L C690

R D146

R D79

L C691

R D146

R D81

L C692

R D146

R D87

L C693

R D146

R D88

L C694

R D146

R D89

L C695

R D146

R D93

L C696

R D146

R D117

L C697

R D146

R D118

L C698

R D146

R D119

L C699

R D146

R D120

L C700

R D146

R D133

L C701

R D146

R D134

L C702

R D146

R D135

L C703

R D146

R D136

L C704

R D146

L C705

R D146

R D147

L C706

R D146

R D149

L C707

R D146

R D151

L C708

R D146

R D154

L C709

R D146

R D155

L C710

R D146

R D161

L C711

R D146

R D175

L C712

R D133

R D3

L C713

R D133

R D5

L C714

R D133

R D3

L C715

R D133

R D18

L C716

R D133

R D20

L C717

R D133

R D22

L C718

R D133

R D37

L C719

R D133

R D40

L C720

R D133

R D41

L C721

R D133

R D42

L C722

R D133

R D43

L C723

R D133

R D48

L C724

R D133

R D49

L C725

R D133

R D54

L C726

R D133

R D58

L C727

R D133

R D59

L C728

R D133

R D78

L C729

R D133

R D79

L C730

R D133

R D81

L C731

R D133

R D87

L C732

R D133

R D88

L C733

R D133

R D89

L C734

R D133

R D93

L C735

R D133

R D117

L C736

R D133

R D118

L C737

R D133

R D119

L C738

R D133

R D120

L C739

R D133

L C740

R D133

R D134

L C741

R D133

R D135

L C742

R D133

R D136

L C743

R D133

R D146

L C744

R D133

R D147

L C745

R D133

R D149

L C746

R D133

R D151

L C747

R D133

R D154

L C748

R D133

R D155

L C749

R D133

R D161

L C750

R D133

R D175

L C751

R D175

R D3

L C752

R D175

R D5

L C753

R D175

R D18

L C754

R D175

R D20

L C755

R D175

R D22

L C756

R D173

R D37

L C757

R D175

R D40

L C758

R D175

R D41

L C759

R D175

R D42

L C760

R D175

R D43

L C761

R D175

R D48

L C762

R D175

R D49

L C763

R D175

R D54

L C764

R D175

R D58

L C765

R D175

R D59

L C766

R D175

R D78

L C767

R D175

R D79

L C768

R D175

R D81

L C769

R D193

L C770

R D194

L C771

R D195

L C772

R D196

L C773

R D197

L C774

R D198

L C775

R D199

L C776

R D200

L C777

R D201

L C778

R D202

L C779

R D203

L C780

R D204

L C781

R D205

L C782

R D206

L C783

R D207

L C784

R D208

L C785

R D209

L C786

R D210

L C787

R D211

L C788

R D212

L C789

R D213

L C790

R D214

L C791

R D215

L C792

R D216

L C793

R D217

L C794

R D218

L C795

R D219

L C796

R D220

L C797

R D221

L C798

R D222

L C799

R D223

L C800

R D224

L C801

R D225

L C802

R D226

L C803

R D227

L C804

R D228

L C805

R D229

L C806

R D230

L C807

R D231

L C808

R D232

L C809

R D233

L C810

R D234

L C811

R D235

L C812

R D236

L C813

R D237

L C814

R D238

L C815

R D239

L C816

R D240

L C817

R D241

L C818

R D242

L C819

R D243

L C820

R D244

L C821

R D245

L C822

R D246

L C823

R D17

R D193

L C824

R D17

R D194

L C825

R D17

R D195

L C826

R D17

R D196

L C827

R D17

R D197

L C828

R D17

R D198

L C829

R D17

R D199

L C830

R D17

R D200

L C831

R D17

R D201

L C832

R D17

R D202

L C833

R D17

R D203

L C834

R D17

R D204

L C835

R D17

R D205

L C836

R D17

R D206

L C837

R D17

R D207

L C838

R D17

R D208

L C839

R D17

R D209

L C840

R D17

R D210

L C841

R D17

R D211

L C842

R D17

R D212

L C843

R D17

R D213

L C844

R D17

R D214

L C845

R D17

R D215

L C846

R D17

R D216

L C847

R D17

R D217

L C848

R D17

R D218

L C849

R D17

R D219

L C850

R D17

R D220

L C851

R D17

R D221

L C852

R D17

R D222

L C853

R D17

R D223

L C854

R D17

R D224

L C855

R D17

R D225

L C856

R D17

R D226

L C857

R D17

R D227

L C858

R D17

R D228

L C859

R D17

R D229

L C860

R D17

R D230

L C861

R D17

R D231

L C862

R D17

R D232

L C863

R D17

R D233

L C864

R D17

R D234

L C865

R D17

R D235

L C866

R D17

R D236

L C867

R D17

R D237

L C868

R D17

R D238

L C869

R D17

R D239

L C870

R D17

R D240

L C871

R D17

R D241

L C872

R D17

R D242

L C873

R D17

R D243

L C874

R D17

R D244

L C875

R D17

R D245

L C876

R D17

R D246

L C877

R D1

R D193

L C878

R D1

R D194

L C879

R D1

R D195

L C880

R D1

R D196

L C881

R D1

R D197

L C882

R D1

R D198

L C883

R D1

R D199

L C884

R D1

R D200

L C885

R D1

R D201

L C886

R D1

R D202

L C887

R D1

R D203

L C888

R D1

R D204

L C889

R D1

R D205

L C890

R D1

R D206

L C891

R D1

R D207

L C892

R D1

R D208

L C893

R D1

R D209

L C894

R D1

R D210

L C895

R D1

R D211

L C896

R D1

R D212

L C897

R D1

R D213

L C898

R D1

R D214

L C899

R D1

R D215

L C900

R D1

R D216

L C901

R D1

R D217

L C902

R D1

R D218

L C903

R D1

R D219

L C904

R D1

R D220

L C905

R D1

R D221

L C906

R D1

R D222

L C907

R D1

R D223

L C908

R D1

R D224

L C909

R D1

R D225

L C910

R D1

R D226

L C911

R D1

R D227

L C912

R D1

R D228

L C913

R D1

R D229

L C914

R D1

R D230

L C915

R D1

R D231

L C916

R D1

R D232

L C917

R D1

R D233

L C918

R D1

R D234

L C919

R D1

R D235

L C920

R D1

R D236

L C921

R D1

R D237

L C922

R D1

R D238

L C923

R D1

R D239

L C924

R D1

R D240

L C925

R D1

R D241

L C926

R D1

R D242

L C927

R D1

R D243

L C928

R D1

R D244

L C929

R D1

R D245

L C930

R D1

R D246

L C931

R D50

R D193

L C932

R D50

R D194

L C933

R D50

R D195

L C934

R D50

R D196

L C935

R D50

R D197

L C936

R D50

R D198

L C937

R D50

R D199

L C938

R D50

R D200

L C939

R D50

R D201

L C940

R D50

R D202

L C941

R D50

R D203

L C942

R D50

R D204

L C943

R D50

R D205

L C944

R D50

R D206

L C945

R D50

R D207

L C946

R D50

R D208

L C947

R D50

R D209

L C948

R D50

R D210

L C949

R D50

R D211

L C950

R D50

R D212

L C951

R D50

R D213

L C952

R D50

R D214

L C953

R D50

R D215

L C954

R D50

R D216

L C955

R D50

R D217

L C956

R D50

R D218

L C957

R D50

R D219

L C958

R D50

R D220

L C959

R D50

R D221

L C960

R D50

R D222

L C961

R D50

R D223

L C962

R D50

R D224

L C963

R D50

R D225

L C964

R D50

R D226

L C965

R D50

R D227

L C966

R D50

R D228

L C967

R D50

R D229

L C968

R D50

R D230

L C969

R D50

R D231

L C970

R D50

R D232

L C971

R D50

R D233

L C972

R D50

R D234

L C973

R D50

R D235

L C974

R D50

R D236

L C975

R D50

R D237

L C976

R D50

R D238

L C977

R D50

R D239

L C978

R D50

R D240

L C979

R D50

R D241

L C980

R D50

R D242

L C981

R D50

R D243

L C982

R D50

R D244

L C983

R D50

R D245

L C984

R D50

R D246

L C985

R D4

R D193

L C986

R D4

R D194

L C987

R D4

R D195

L C988

R D4

R D196

L C989

R D4

R D197

L C990

R D4

R D198

L C991

R D4

R D199

L C992

R D4

R D200

L C993

R D4

R D201

L C994

R D4

R D202

L C995

R D4

R D203

L C996

R D4

R D204

L C997

R D4

R D205

L C998

R D4

R D206

L C999

R D4

R D207

L C1000

R D4

R D208

L C1001

R D4

R D209

L C1002

R D4

R D210

L C1003

R D4

R D211

L C1004

R D4

R D212

L C1005

R D4

R D211

L C1006

R D4

R D214

L C1007

R D4

R D215

L C1008

R D4

R D216

L C1009

R D4

R D217

L C1010

R D4

R D218

L C1011

R D4

R D219

L C1012

R D4

R D220

L C1013

R D4

R D221

L C1014

R D4

R D222

L C1015

R D4

R D223

L C1016

R D4

R D224

L C1017

R D4

R D225

L C1018

R D4

R D226

L C1019

R D4

R D227

L C1020

R D4

R D228

L C1021

R D4

R D229

L C1022

R D4

R D230

L C1023

R D4

R D231

L C1024

R D4

R D232

L C1025

R D4

R D233

L C1026

R D4

R D234

L C1027

R D4

R D235

L C1028

R D4

R D236

L C1029

R D4

R D237

L C1030

R D4

R D238

L C1031

R D4

R D239

L C1032

R D4

R D240

L C1033

R D4

R D241

L C1034

R D4

R D242

L C1035

R D4

R D243

L C1036

R D4

R D244

L C1037

R D4

R D245

L C1038

R D4

R D246

L C1039

R D145

R D193

L C1040

R D145

R D194

L C1041

R D145

R D195

L C1042

R D145

R D196

L C1043

R D145

R D197

L C1044

R D145

R D198

L C1045

R D145

R D199

L C1046

R D145

R D200

L C1047

R D145

R D201

L C1048

R D145

R D202

L C1049

R D145

R D203

L C1050

R D145

R D204

L C1051

R D145

R D205

L C1052

R D145

R D206

L C1053

R D145

R D207

L C1054

R D145

R D208

L C1055

R D145

R D209

L C1056

R D145

R D210

L C1057

R D145

R D211

L C1058

R D145

R D212

L C1059

R D145

R D213

L C1060

R D145

R D214

L C1061

R D145

R D215

L C1062

R D145

R D216

L C1063

R D145

R D217

L C1064

R D145

R D218

L C1065

R D145

R D219

L C1066

R D145

R D220

L C1067

R D145

R D221

L C1068

R D145

R D222

L C1069

R D145

R D223

L C1070

R D145

R D224

L C1071

R D145

R D225

L C1072

R D145

R D226

L C1073

R D145

R D227

L C1074

R D145

R D228

L C1075

R D145

R D229

L C1076

R D145

R D230

L C1077

R D145

R D231

L C1078

R D145

R D232

L C1079

R D145

R D233

L C1080

R D145

R D234

L C1081

R D145

R D235

L C1082

R D145

R D236

L C1083

R D145

R D237

L C1084

R D145

R D238

L C1085

R D145

R D239

L C1086

R D145

R D240

L C1087

R D145

R D241

L C1088

R D145

R D242

L C1089

R D145

R D243

L C1090

R D145

R D244

L C1091

R D145

R D245

L C1092

R D145

R D246

L C1093

R D9

R D193

L C1094

R D9

R D194

L C1095

R D9

R D195

L C1096

R D9

R D196

L C1097

R D9

R D197

L C1098

R D9

R D198

L C1099

R D9

R D199

L C1100

R D9

R D200

L C1101

R D9

R D201

L C1102

R D9

R D202

L C1103

R D9

R D203

L C1104

R D9

R D204

L C1105

R D9

R D205

L C1106

R D9

R D206

L C1107

R D9

R D207

L C1108

R D9

R D208

L C1109

R D9

R D209

L C1110

R D9

R D210

L C1111

R D9

R D211

L C1112

R D9

R D212

L C1113

R D9

R D213

L C1114

R D9

R D214

L C1115

R D9

R D215

L C1116

R D9

R D216

L C1117

R D9

R D217

L C1118

R D9

R D218

L C1119

R D9

R D210

L C1120

R D9

R D220

L C1121

R D9

R D221

L C1122

R D9

R D222

L C1123

R D9

R D223

L C1124

R D9

R D224

L C1125

R D9

R D225

L C1126

R D9

R D226

L C1127

R D9

R D227

L C1128

R D9

R D228

L C1129

R D9

R D229

L C1130

R D9

R D230

L C1131

R D9

R D231

L C1132

R D9

R D232

L C1133

R D9

R D433

L C1134

R D9

R D234

L C1135

R D9

R D235

L C1136

R D9

R D236

L C1137

R D9

R D237

L C1138

R D9

R D238

L C1139

R D9

R D239

L C1140

R D9

R D240

L C1141

R D9

R D241

L C1142

R D9

R D242

L C1143

R D9

R D243

L C1144

R D9

R D244

L C1145

R D9

R D245

L C1146

R D9

R D246

L C1147

R D168

R D193

L C1148

R D168

R D194

L C1149

R D168

R D195

L C1150

R D168

R D196

L C1151

R D168

R D197

L C1152

R D168

R D198

L C1153

R D168

R D199

L C1154

R D168

R D200

L C1155

R D168

R D201

L C1156

R D168

R D202

L C1157

R D168

R D203

L C1158

R D168

R D204

L C1159

R D168

R D205

L C1160

R D168

R D206

L C1161

R D168

R D207

L C1162

R D168

R D208

L C1163

R D168

R D209

L C1164

R D168

R D210

L C1165

R D168

R D211

L C1166

R D168

R D212

L C1167

R D168

R D213

L C1168

R D168

R D214

L C1169

R D168

R D215

L C1170

R D168

R D216

L C1171

R D168

R D217

L C1172

R D168

R D218

L C1173

R D168

R D219

L C1174

R D168

R D220

L C1175

R D168

R D221

L C1176

R D168

R D222

L C1177

R D168

R D223

L C1178

R D168

R D224

L C1179

R D168

R D225

L C1180

R D168

R D226

L C1181

R D168

R D227

L C1182

R D168

R D228

L C1183

R D168

R D229

L C1184

R D168

R D230

L C1185

R D168

R D231

L C1186

R D168

R D232

L C1187

R D168

R D233

L C1188

R D168

R D234

L C1189

R D168

R D235

L C1190

R D168

R D236

L C1191

R D168

R D237

L C1192

R D168

R D238

L C1193

R D168

R D239

L C1194

R D168

R D240

L C1195

R D168

R D241

L C1196

R D168

R D242

L C1197

R D168

R D243

L C1198

R D168

R D244

L C1199

R D168

R D245

L C1200

R D168

R D246

L C1201

R D10

R D193

L C1202

R D10

R D194

L C1203

R D10

R D195

L C1204

R D10

R D196

L C1205

R D10

R D197

L C1206

R D10

R D198

L C1207

R D10

R D199

L C1208

R D10

R D200

L C1209

R D10

R D201

L C1210

R D10

R D202

L C1211

R D10

R D203

L C1212

R D10

R D204

L C1213

R D10

R D205

L C1214

R D10

R D206

L C1215

R D10

R D207

L C1216

R D10

R D208

L C1217

R D10

R D209

L C1218

R D10

R D210

L C1219

R D10

R D211

L C1220

R D10

R D212

L C1221

R D10

R D213

L C1222

R D10

R D214

L C1223

R D10

R D215

L C1224

R D10

R D216

L C1225

R D10

R D217

L C1226

R D10

R D218

L C1227

R D10

R D219

L C1228

R D10

R D220

L C1229

R D10

R D221

L C1230

R D10

R D222

L C1231

R D10

R D223

L C1232

R D10

R D224

L C1233

R D10

R D225

L C1234

R D10

R D226

L C1235

R D10

R D227

L C1236

R D10

R D228

L C1237

R D10

R D229

L C1238

R D10

R D230

L C1239

R D10

R D231

L C1240

R D10

R D232

L C1241

R D10

R D233

L C1242

R D10

R D234

L C1243

R D10

R D235

L C1244

R D10

R D236

L C1245

R D10

R D237

L C1246

R D10

R D238

L C1247

R D10

R D239

L C1248

R D10

R D240

L C1249

R D10

R D241

L C1250

R D10

R D242

L C1251

R D10

R D243

L C1252

R D10

R D244

L C1253

R D10

R D245

L C1254

R D10

R D246

L C1255

R D55

R D193

L C1256

R D55

R D194

L C1257

R D55

R D195

L C1258

R D55

R D196

L C1259

R D55

R D197

L C1260

R D55

R D198

L C1261

R D55

R D199

L C1262

R D55

R D200

L C1263

R D55

R D201

L C1264

R D55

R D202

L C1265

R D55

R D203

L C1266

R D55

R D204

L C1267

R D55

R D205

L C1268

R D55

R D206

L C1269

R D55

R D207

L C1270

R D55

R D208

L C1271

R D55

R D209

L C1272

R D55

R D210

L C1273

R D55

R D211

L C1274

R D55

R D212

L C1275

R D55

R D213

L C1276

R D55

R D214

L C1277

R D55

R D213

L C1278

R D55

R D216

L C1279

R D55

R D217

L C1280

R D55

R D218

L C1281

R D55

R D219

L C1282

R D55

R D220

L C1283

R D55

R D221

L C1284

R D55

R D222

L C1285

R D55

R D223

L C1286

R D55

R D224

L C1287

R D55

R D223

L C1288

R D55

R D226

L C1289

R D55

R D227

L C1290

R D55

R D228

L C1291

R D55

R D229

L C1292

R D55

R D230

L C1293

R D55

R D231

L C1294

R D55

R D232

L C1295

R D55

R D233

L C1296

R D55

R D234

L C1297

R D55

R D235

L C1298

R D55

R D236

L C1299

R D55

R D237

L C1300

R D55

R D238

L C1301

R D55

R D239

L C1302

R D55

R D240

L C1303

R D55

R D241

L C1304

R D55

R D242

L C1305

R D55

R D243

L C1306

R D55

R D244

L C1307

R D55

R D245

L C1308

R D55

R D246

L C1309

R D37

R D193

L C1310

R D37

R D194

L C1311

R D37

R D195

L C1312

R D37

R D196

L C1313

R D37

R D197

L C1314

R D37

R D198

L C1315

R D37

R D199

L C1316

R D37

R D200

L C1317

R D37

R D201

L C1318

R D37

R D202

L C1319

R D37

R D203

L C1320

R D37

R D204

L C1321

R D37

R D205

L C1322

R D37

R D206

L C1323

R D37

R D207

L C1324

R D37

R D208

L C1325

R D37

R D209

L C1326

R D37

R D210

L C1327

R D37

R D211

L C1328

R D37

R D212

L C1329

R D37

R D213

L C1330

R D37

R D214

L C1331

R D37

R D215

L C1332

R D37

R D216

L C1333

R D37

R D217

L C1334

R D37

R D218

L C1335

R D37

R D219

L C1336

R D37

R D220

L C1337

R D37

R D221

L C1338

R D37

R D222

L C1339

R D37

R D223

L C1340

R D37

R D224

L C1341

R D37

R D225

L C1342

R D37

R D226

L C1343

R D37

R D227

L C1344

R D37

R D228

L C1345

R D37

R D229

L C1346

R D37

R D230

L C1347

R D37

R D231

L C1348

R D37

R D232

L C1349

R D37

R D233

L C1350

R D37

R D234

L C1351

R D37

R D235

L C1352

R D37

R D236

L C1353

R D37

R D237

L C1354

R D37

R D238

L C1355

R D37

R D239

L C1356

R D37

R D240

L C1357

R D37

R D241

L C1358

R D37

R D242

L C1359

R D37

R D243

L C1360

R D37

R D244

L C1361

R D37

R D245

L C1362

R D37

R D246

L C1363

R D143

R D193

L C1364

R D143

R D194

L C1365

R D143

R D195

L C1366

R D143

R D196

L C1367

R D143

R D197

L C1368

R D143

R D198

L C1369

R D143

R D199

L C1370

R D143

R D200

L C1371

R D143

R D201

L C1372

R D143

R D202

L C1373

R D143

R D203

L C1374

R D143

R D204

L C1375

R D143

R D205

L C1376

R D143

R D206

L C1377

R D143

R D207

L C1378

R D143

R D208

L C1379

R D143

R D209

L C1380

R D143

R D210

L C1381

R D143

R D211

L C1382

R D143

R D212

L C1383

R D143

R D213

L C1384

R D143

R D214

L C1385

R D143

R D215

L C1386

R D143

R D216

L C1387

R D143

R D217

L C1388

R D143

R D218

L C1389

R D143

R D219

L C1390

R D143

R D220

L C1391

R D143

R D221

L C1392

R D143

R D222

L C1393

R D143

R D223

L C1394

R D143

R D224

L C1395

R D143

R D225

L C1396

R D143

R D226

L C1397

R D143

R D227

L C1398

R D143

R D228

L C1399

R D143

R D229

L C1400

R D143

R D230

L C1401

R D143

R D231

L C1402

R D143

R D232

L C1403

R D143

R D233

L C1404

R D143

R D234

L C1405

R D143

R D235

L C1406

R D143

R D236

L C1407

R D143

R D237

L C1408

R D143

R D238

L C1409

R D143

R D239

L C1410

R D143

R D240

L C1411

R D143

R D241

L C1412

R D143

R D242

L C1413

R D143

R D243

L C1414

R D143

R D244

L C1415

R D143

R D245

L C1416

R D143

R D246

wherein R D1 to R D246 have the following structures:

13 . The compound of claim 10 , wherein the compound has the Formula IV:

wherein:

M 1 is Pd or Pt;

moieties E and F are each independently monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;

Z 5 and Z 6 are each independently C or N;

K 3 , and K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least two of them are direct bonds;

L 1 , L 2 , and L 3 are each independently selected from the group consisting of a single bond, absent a bond, O, S, CR′R″, SiR′R″, BR′, P(O)R, and NR′, 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′, 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, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof;

two adjacent R A , R B , R E , and R F can be joined or fused together to form a ring where chemically feasible; and

K 1 , K 2 , Z 1 -Z 4 , L, R A , R B , and rings A and B are all defined the same as above.

14 . The compound of claim 13 , wherein the compound is selected from the group consisting of the following compounds:

wherein: R x and R y are each selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, aryl, heteroaryl, and combinations thereof; R G for each occurrence is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and K 1 , K 2 , Z 1 -Z 4 , L, R A , R B , and rings A and B are all defined the same as above.

15 . The compound of claim 13 , wherein the compound is selected from the group consisting of the following compounds:

16 . The compound of claim 1 , wherein the compound is selected from the group consisting of the following compounds:

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 compound comprising a ligand L A of Formula I:

wherein

ring A and ring B each independently represents a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

Z 1 , Z 2 , Z 3 and Z 4 are each independently C or N;

L is a direct bond or selected from the group consisting of O, S, NR″, CR′R″, SiR′R″, BR′, P(O)R, and BR′R″;

K 1 and K 2 are each independently selected from the group consisting of direct bond, O, and S;

R A represents mono to the maximum allowable substitution;

at least one of R A or R B comprises a structure of Formula II or Formula III:

the dashed lines of Formula II and Formula III indicate direct bond to ring A or ring B;

X is selected from the group consisting of BR′, C═O, C═S, C═NR′, CR′R″ and SiR′R″;

Y 1 and Y 2 are each independently selected from the group consisting of O, S, NR′, and BR′;

ring C is a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

R B and R C each independently represent mono to the maximum allowable substitution, or no substitution;

L A is coordinated to a metal M through the dashed lines of Formula I, forming a 5-membered or 6-membered chelate ring;

M is optionally coordinated to other ligands;

L A is optionally joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two of adjacent R, R′, R″, R A , R B , and R C can be joined or fused together to form a ring;

when Y 1 and Y 2 of Formula II are independently selected from the group consisting of O and NR′, X is not CR′R″; and

when one of ring A or ring B is a 5-membered ring and one of R A or R B comprises a structure of Formula II, then X is not CR′R″.

18 . The OLED of claim 17 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 512-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-512-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 18 , wherein the host is selected from the group consisting of the following hosts:

and combinations thereof.

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 ligand L A of Formula I:

wherein

ring A and ring B each independently represents a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

Z 1 , Z 2 , Z 3 and Z 4 are each independently C or N;

L is a direct bond or selected from the group consisting of O, S, NR″, CR′R″, SiR′R″, BR′, P(O)R, and BR′R″;

K 1 and K 2 are each independently selected from the group consisting of direct bond, O, and S;

R A represents mono to the maximum allowable substitution;

at least one of R A or R B comprises a structure of Formula II or Formula III:

the dashed lines of Formula II and Formula III indicate direct bond to ring A or ring B;

X is selected from the group consisting of BR′, C═O, C═S, C═NR′, CR′R″ and SiR′R″;

Y 1 and Y 2 are each independently selected from the group consisting of O, S, NR′, and BR′;

ring C is a monocyclic or multicyclic fused ring system comprised of one or more 5-membered or 6-membered carbocyclic or heterocyclic rings;

R B and R C each independently represent mono to the maximum allowable substitution, or no substitution;

L A is coordinated to a metal M through the dashed lines of Formula I, forming a 5-membered or 6-membered chelate ring;

M is optionally coordinated to other ligands;

L A is optionally joined with other ligands to comprise a tridentate, tetradentate, pentadentate, or hexadentate ligand;

any two of adjacent R, R′, R″, R A , R B , and R C can be joined or fused together to form a ring;

when Y 1 and Y 2 of Formula II are independently selected from the group consisting of O and NR′, X is not CR′R″; and

when one of ring A or ring B is a 5-membered ring and one of R A or R B comprises a structure of Formula II, then X is not CR′R″.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 31, 2022

From: PALMER, NEIL; SHIH, WEI-CHUN; FITZGERALD, GEORGE; MACOR, JOSEPH A.; HAMZE, RASHA; BOUDREAULT, PIERRE-LUC T.; SZIGETHY, GEZA

To: UNIVERSAL DISPLAY CORPORATION

Reel/Frame 059457/0786 →

Continuity (2)

Provisional Application 63200962 · Apr 6, 2021

Related Publication 20220352477A1 · Nov 3, 2022

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