IP Library › Granted Patent US 12,552,821
Granted Patent B2
US 12,552,821 · App. 17/718,430 · Granted Feb 17, 2026

Organic electroluminescent material and device thereof

Inventors: Zhen Wang (Beijing, CN); Hongbo Li (Beijing, CN); Ming Sang (Beijing, CN); Wei Cai (Beijing, CN); Chi Yuen Raymond Kwong (Beijing, CN); Chuanjun Xia (Beijing, CN)
Assignee: BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD.
C07F15/0033H10K85/342H10K85/622H10K85/626H10K85/654H10K85/6572H10K85/6574H10K85/6576
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Quick Facts
Patent No.
US 12,552,821
App. No.
17/718,430
Granted
Feb 17, 2026
Kind
B2
Abstract

Provided are an organic electroluminescent material and a device thereof. The organic electroluminescent material is a metal complex including a ligand L a having a structure of Formula 1, and the metal complex can be used as luminescent materials in electroluminescent devices. These new compounds, when used in electroluminescent devices, can show better performance, provide lower device voltage and higher device efficiency, and significantly improve the comprehensive performance of devices. Further provided are an electroluminescent device including the metal complex and a compound composition including the metal complex.

Claims (5277)

1 . A metal complex, comprising a metal M and a ligand L a coordinated with the metal M, wherein the metal M is selected from metals having a relative atomic mass greater than 40, and L a has a structure represented by Formula 1:

wherein in Formula 1,

Cy is, at each occurrence identically or differently, selected from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms or combinations thereof;

X is selected from the group consisting of O, S, Se, NR′, CR′R′, SiR′R′, and GeR′R′; when two R′ are present, the two R′ are identical or different;

X 1 to X 7 are, at each occurrence identically or differently, selected from C, CR x or N; at least one of X 1 to X 4 is C and is attached to Cy;

X 1 , X 2 , X 3 or X 4 is attached to the metal M through a metal-carbon bond or a metal-nitrogen bond;

at least one of X 1 to X 7 is CR x , wherein the R x is cyano or fluorine;

A has a structure represented by Formula 2:

wherein a is selected from 1;

A 1 is, at each occurrence identically or differently, selected from the group consisting of the following groups unsubstituted or substituted by one or at least two R a1 : alkylene having 1 to 20 carbon atoms, heteroalkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms, heterocyclene having 3 to 20 ring atoms, phenylene, and heteroarylene having 5 to 6 ring atoms, and combinations thereof;

A 2 is, at each occurrence identically or differently, selected from the group consisting of the following groups unsubstituted or substituted by one or at least two R a2 : cycloalkylene having 3 to 20 carbon atoms, heterocyclene having 3 to 20 ring atoms, and combinations thereof;

R′, R x , R a1 , R a2 , and R a3 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R′, R x , R a2 , R a3 can be optionally joined to form a ring;

the length of A is at least 6.7 Å;

“*” represents a position where A is attached;

when A 1 is selected from phenylene unsubstituted or substituted by one or at least two R a1 or heteroarylene having 5 to 6 ring atoms unsubstituted or substituted by one or at least two R a1 , A 2 and R a1 need to satisfy the following conditions:

1) A 2 that is directly attached to A 1 is, at each occurrence identically or differently, selected from the group consisting of: following groups unsubstituted or substituted by one or at least two R a2 : cycloalkylene having 3 to 20 carbon atoms and heterocyclene having 3 to 20 ring atoms, and combinations thereof; and

2) R a1 is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

2 . The metal complex of claim 1 , wherein A 1 is, at each occurrence identically or differently, selected from phenylene unsubstituted or substituted by one or at least two R a1 or heteroarylene having 5 to 6 ring atoms unsubstituted or substituted by one or at least two R a1 ; A 2 is, at each occurrence identically or differently, selected from the group consisting of the following groups following groups unsubstituted or substituted by one or at least two R a2 : cycloalkylene having 3 to 20 ring carbon atoms and heterocyclene having 3 to 20 ring atoms, and combinations thereof.

3 . The metal complex of claim 1 , wherein A 1 is, at each occurrence identically or differently, selected from the group consisting of the following groups unsubstituted or substituted by one or at least two R a1 : alkylene having 1 to 20 carbon atoms, heteroalkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms and heterocyclene having 3 to 20 ring atoms, and combinations thereof; A 2 is, at each occurrence identically or differently, selected from following groups unsubstituted or substituted by one or at least two R a2 : cycloalkylene having 3 to 20 carbon atoms, heterocyclene having 3 to 20 ring atoms, and combinations thereof.

4 . The metal complex of claim 1 , wherein Cy is selected from any one of the group consisting of the following structures:

wherein,

R represents, at each occurrence identically or differently, mono-substitution, multiple substitutions or no substitution; when a plurality of R are present in any one of those structures, the plurality of R are identical or different;

R is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, a cyano group, an isocyano group, and combinations thereof;

two adjacent substituents R can be optionally joined to form a ring;

“#” represents a position where the metal M is attached, and

represents a position where X 1 , X 2 , X 3 or X 4 is attached.

5 . The metal complex of claim 1 , wherein the metal complex has a general formula of M(L a ) m (L b ) n (L c ) q ;

wherein,

M is, at each occurrence identically or differently, selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt;

L a , L b , and L c are a first ligand, a second ligand and a third ligand coordinated to the metal M, respectively, and L c is identical to or different from L a or L b ; wherein L a , L b , and L c can be optionally joined to form a multidentate ligand;

m is selected from 1, 2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, and m+n+q equals an oxidation state of the metal M; when m is greater than or equal to 2, a plurality of L a are identical or different; when n is equal to 2, two L b are identical or different; when q is equal to 2, two L c are identical or different;

L a is, at each occurrence identically or differently, selected from the group consisting of:

X is selected from the group consisting of O, S, Se, NR′, CR′R′, SiR′R′, and GeR′R′; when two R′ are present, the two R′ are identical or different;

R and R x represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or no substitution;

at least one of R x is fluorine or cyano;

A has a structure represented by Formula 2:

wherein a is selected from 1, 2, 3, 4 or 5;

A 1 is, at each occurrence identically or differently, selected from the group consisting of the following groups unsubstituted or substituted by one or at least two R a1 : alkylene having 1 to 20 carbon atoms, heteroalkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms, heterocyclene having 3 to 20 ring atoms, phenylene and heteroarylene having 5 to 6 ring atoms, and combinations thereof;

A 2 is, at each occurrence identically or differently, selected from the group consisting of the following groups unsubstituted or substituted by one or at least two R a2 : cycloalkylene having 3 to 20 carbon atoms, heterocyclene having 3 to 20 ring atoms, and combinations thereof;

R, R′, R″, R x , R a1 , R a2 , and R a3 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R, R′, R″, R x , R a2 , R a3 can be optionally joined to form a ring;

the length of A is at least 6.7 Å;

“*” represents a position where A is attached;

when A 1 is selected from phenylene unsubstituted or substituted by one or at least two Ral or heteroarylene having 5 to 6 ring atoms unsubstituted or substituted by one or at least two R a1 , A 2 and R a1 need to satisfy the following conditions:

1) A 2 that is directly attached to A 1 is, at each occurrence identically or differently, selected from the group consisting of: cycloalkylene having 3 to 20 carbon atoms unsubstituted or substituted by one or at least two R a2 , heterocyclene having 3 to 20 ring atoms unsubstituted or substituted by one or at least two R a2 , and combinations thereof; and

2) R a1 is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

L b and L c are, at each occurrence identically or differently, selected from the group consisting of the following structures:

wherein,

R a and R b represent, at each occurrence identically or differently, mono-substitution, multiple substitutions or no substitution;

X b is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NR N1 , and CR C1 R C2 ;

R a , R b , R c , R N1 , R C1 , and R C2 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R a , R b , R c , R N1 , R C1 , and R C2 can be optionally joined to form a ring.

6 . The metal complex of claim 5 , wherein L a is, at each occurrence identically or differently, selected from the group consisting of:

7 . The metal complex of claim 6 , wherein L b is, at each occurrence identically or differently, selected from the group consisting of:

8 . The metal complex of claim 7 , wherein Le is, at each occurrence identically or differently, selected from the group consisting of:

9 . The metal complex of claim 8 , wherein the metal complex has a structure of Ir(L a ) 2 (L b ) or Ir(L a )(L b ) 2 or Ir(L a ) 3 , wherein L a is, at each occurrence identically or differently, selected from any one or any two or any three of the group consisting of L a12 to L a77 , L a91 to L a94 , L a98 to L a102 , L a111 to L a114 , L a142 to L a150 , L a153 to L a173 , L a177 to L a192 , L a195 to L a200 , L a229 to L a306 , L a327 to L a360 , L a381 to L a456 , L a466 to L a477 , L a482 to L a488 , L a490 , L a495 to L a501 , L a503 , L a517 to L a582 , L a596 to L a599 , L a603 to L a607 , L a616 to L a19 , L a647 to L a655 , L a670 to L a675 , L a678 to L a761 , L a782 to L a793 , L a804 to L a877 , L a887 to L a900 , L a903 to L a909 , L a911 to L a912 , L a916 to L a922 , L a924 , L a928 to L a934 , L a936 , L a938 , and L b is selected from any one or any two of the group consisting of L b1 to L b328 ; or

the metal complex has a structure of Ir(L a ) 2 (L c ) or Ir(L a )(L c ) 2 , wherein L a is, at each occurrence identically or differently, selected from any one or any two of the group consisting of L a12 to L a77 , L a91 to L a94 , L a98 to L a102 , L a111 to L a114 , L a142 to L a150 , L a153 to L a173 , L a177 to L a192 , L a195 to L a200 , L a229 to L a306 , L a327 to L a360 , L a381 to L a456 , L a466 to L a477 , L a482 to L a488 , L a490 , L a495 to L a501 , L a503 , L a517 to L a582 , L a596 to L a599 , L a603 to L a607 , L a616 to L a19 , L a647 to L a655 , L a670 to L a675 , L a678 to L a761 , L a782 to L a793 , L a804 to L a877 , L a887 to L a900 , L a903 to L a909 , L a911 to L a912 , L a916 to L a922 , L a924 , L a928 to L a934 , L a936 , L a938 , and L c is selected from any one or any two of the group consisting of L c1 to L c360 ; or

the metal complex has a structure of Ir(L a )(L b )(L c ), wherein L a is, at each occurrence identically or differently, selected from any one of the group consisting of L a12 to L a77 , L a91 to L a94 , L a98 to L a102 , L a111 to L a114 , L a142 to L a150 , L a153 to L a173 , L a177 to L a192 , L a195 to L a200 , L a229 to L a306 , L a327 to L a360 , L a381 to L a456 , L a466 to L a477 , L a482 to L a488 , L a490 , L a495 to L a501 , L a503 , L a517 to L a582 , L a596 to L a599 , L a603 to L a607 , L a616 to L a19 , L a647 to L a655 , L a670 to L a675 , L a678 to L a761 , L a782 to L a793 , L a804 to L a877 , L a887 to L a900 , L a903 to L a909 , L a911 to L a912 , L a916 to L a922 , L a924 , L a928 to L a934 , L a936 , L a938 , L b is selected from any one of the group consisting of L b1 to L b328 , and L c is selected from any one of the group consisting of L c1 to L c360 ;

wherein the metal complex is selected from the group consisting of metal complex 39 to metal complex 266, metal complex 305 to metal complex 1102, metal complex 1179 to metal complex 1824, metal complex 1863 to metal complex 1900, wherein metal complex 39 to metal complex 266, metal complex 305 to metal complex 1102, metal complex 1179 to metal complex 1824, metal complex 1863 to metal complex 1900 have a structure of IrL a (L b ) 2 , wherein two L b are identical, and L a and L b correspond to structures in the following table, respectively:

Metal

Metal

complex

L a

L b

complex

L a

L b

39

L a13

L b1

40

L a13

L b3

41

L a13

L b4

42

L a13

L b8

43

L a13

L b10

44

L a13

L b12

45

L a13

L b13

46

L a13

L b17

47

L a13

L b21

48

L a13

L b22

49

L a13

L b26

50

L a13

L b28

51

L a13

L b30

52

L a13

L b31

53

L a13

L b35

54

L a13

L b37

55

L a13

L b38

56

L a13

L b39

57

L a13

L b40

58

L a13

L b41

59

L a13

L b42

60

L a13

L b43

61

L a13

L b44

62

L a13

L b45

63

L a13

L b71

64

L a13

L b72

65

L a13

L b79

66

L a13

L b80

67

L a13

L b81

68

L a13

L b99

69

L a13

L b112

70

L a13

L b151

71

L a13

L b153

72

L a13

L b164

73

L a13

L b166

74

L a13

L b209

75

L a13

L b287

76

L a13

L b299

77

L a14

L b1

78

L a14

L b3

79

L a14

L b4

80

L a14

L b8

81

L a14

L b10

82

L a14

L b12

83

L a14

L b13

84

L a14

L b17

85

L a14

L b21

86

L a14

L b22

87

L a14

L b26

88

L a14

L b28

89

L a14

L b30

90

L a14

L b31

91

L a14

L b35

92

L a14

L b37

93

L a14

L b38

94

L a14

L b39

95

L a14

L b40

96

L a14

L b41

97

L a14

L b42

98

L a14

L b43

99

L a14

L b44

100

L a14

L b45

101

L a14

L b71

102

L a14

L b72

103

L a14

L b79

104

L a14

L b80

105

L a14

L b81

106

L a14

L b99

107

L a14

L b112

108

L a14

L b151

109

L a14

L b153

110

L a14

L b164

111

L a14

L b166

112

L a14

L b209

113

L a14

L b287

114

L a14

L b299

115

L a18

L b1

116

L a18

L b3

117

L a18

L b4

118

L a18

L b8

119

L a18

L b10

120

L a18

L b12

121

L a18

L b13

122

L a18

L b17

123

L a18

L b21

124

L a18

L b22

125

L a18

L b26

126

L a18

L b28

127

L a18

L b30

128

L a18

L b31

129

L a18

L b35

130

L a18

L b37

131

L a18

L b38

132

L a18

L b39

133

L a18

L b40

134

L a18

L b41

135

L a18

L b42

136

L a18

L b43

137

L a18

L b44

138

L a18

L b45

139

L a18

L b71

140

L a18

L b72

141

L a18

L b79

142

L a18

L b80

143

L a18

L b81

144

L a18

L b99

145

L a18

L b112

146

L a18

L b151

147

L a18

L b153

148

L a18

L b164

149

L a18

L b166

150

L a18

L b209

151

L a18

L b287

152

L a18

L b299

153

L a20

L b1

154

L a20

L b3

155

L a20

L b4

156

L a20

L b8

157

L a20

L b10

158

L a20

L b12

159

L a20

L b13

160

L a20

L b17

161

L a20

L b21

162

L a20

L b22

163

L a20

L b26

164

L a20

L b28

165

L a20

L b30

166

L a20

L b31

167

L a20

L b35

168

L a20

L b37

169

L a20

L b38

170

L a20

L b39

171

L a20

L b40

172

L a20

L b41

173

L a20

L b42

174

L a20

L b43

175

L a20

L b44

176

L a20

L b45

177

L a20

L b71

178

L a20

L b72

179

L a20

L b79

180

L a20

L b80

181

L a20

L b81

182

L a20

L b99

183

L a20

L b112

184

L a20

L b151

185

L a20

L b153

186

L a20

L b164

187

L a20

L b166

188

L a20

L b209

189

L a20

L b287

190

L a20

L b299

191

L a57

L b1

192

L a57

L b3

193

L a57

L b4

194

L a57

L b8

195

L a57

L b10

196

L a57

L b12

197

L a57

L b13

198

L a57

L b17

199

L a57

L b21

200

L a57

L b22

201

L a57

L b26

202

L a57

L b28

203

L a57

L b30

204

L a57

L b31

205

L a57

L b35

206

L a57

L b37

207

L a57

L b38

208

L a57

L b39

209

L a57

L b40

210

L a57

L b41

211

L a57

L b42

212

L a57

L b43

213

L a57

L b44

214

L a57

L b45

215

L a57

L b71

216

L a57

L b72

217

L a57

L b79

218

L a57

L b80

219

L a57

L b81

220

L a57

L b99

221

L a57

L b112

222

L a57

L b151

223

L a57

L b153

224

L a57

L b164

225

L a57

L b166

226

L a57

L b209

227

L a57

L b287

228

L a57

L b299

229

L a70

L b1

230

L a70

L b3

231

L a70

L b4

232

L a70

L b8

233

L a70

L b10

234

L a70

L b12

235

L a70

L b13

236

L a70

L b17

237

L a70

L b21

238

L a70

L b22

239

L a70

L b26

240

L a70

L b28

241

L a70

L b30

242

L a70

L b31

243

L a70

L b35

244

L a70

L b37

245

L a70

L b38

246

L a70

L b39

247

L a70

L b40

248

L a70

L b41

249

L a70

L b42

250

L a70

L b43

251

L a70

L b44

252

L a70

L b45

253

L a70

L b71

254

L a70

L b72

255

L a70

L b79

256

L a70

L b80

257

L a70

L b81

258

L a70

L b99

259

L a70

L b112

260

L a70

L b151

261

L a70

L b153

262

L a70

L b164

263

L a70

L b166

264

L a70

L b209

265

L a70

L b287

266

L a70

L b299

305

L a92

L b1

306

L a92

L b3

307

L a92

L b4

308

L a92

L b8

309

L a92

L b10

310

L a92

L b12

311

L a92

L b13

312

L a92

L b17

313

L a92

L b21

314

L a92

L b22

315

L a92

L b26

316

L a92

L b28

317

L a92

L b30

318

L a92

L b31

319

L a92

L b35

320

L a92

L b37

321

L a92

L b38

322

L a92

L b39

323

L a92

L b40

324

L a92

L b41

325

L a92

L b42

326

L a92

L b43

327

L a92

L b44

328

L a92

L b45

329

L a92

L b71

330

L a92

L b72

331

L a92

L b79

332

L a92

L b80

333

L a92

L b81

334

L a92

L b99

335

L a92

L b112

336

L a92

L b151

337

L a92

L b153

338

L a92

L b164

339

L a92

L b166

340

L a92

L b209

341

L a92

L b287

342

L a92

L b299

343

L a113

L b1

344

L a113

L b3

345

L a113

L b4

346

L a113

L b8

347

L a113

L b10

348

L a113

L b12

349

L a113

L b13

350

L a113

L b17

351

L a113

L b21

352

L a113

L b22

353

L a113

L b26

354

L a113

L b28

355

L a113

L b30

356

L a113

L b31

357

L a113

L b35

358

L a113

L b37

359

L a113

L b38

360

L a113

L b39

361

L a113

L b40

362

L a113

L b41

363

L a113

L b42

364

L a113

L b43

365

L a113

L b44

366

L a113

L b45

367

L a113

L b71

368

L a113

L b72

369

L a113

L b79

370

L a113

L b80

371

L a113

L b81

372

L a113

L b99

373

L a113

L b112

374

L a113

L b151

375

L a113

L b153

376

L a113

L b164

377

L a113

L b166

378

L a113

L b209

379

L a113

L b287

380

L a113

L b299

381

L a231

L b1

382

L a231

L b3

383

L a231

L b4

384

L a231

L b8

385

L a231

L b10

386

L a231

L b12

387

L a231

L b13

388

L a231

L b17

389

L a231

L b21

390

L a231

L b22

391

L a231

L b26

392

L a231

L b28

393

L a231

L b30

394

L a231

L b31

395

L a231

L b35

396

L a231

L b37

397

L a231

L b38

398

L a231

L b39

399

L a231

L b40

400

L a231

L b41

401

L a231

L b42

402

L a231

L b43

403

L a231

L b44

404

L a231

L b45

405

L a231

L b71

406

L a231

L b72

407

L a231

L b79

408

L a231

L b80

409

L a231

L b81

410

L a231

L b99

411

L a231

L b112

412

L a231

L b151

413

L a231

L b153

414

L a231

L b164

415

L a231

L b166

416

L a231

L b209

417

L a231

L b287

418

L a231

L b299

419

L a236

L b1

420

L a236

L b3

421

L a236

L b4

422

L a236

L b8

423

L a236

L b10

424

L a236

L b12

425

L a236

L b13

426

L a236

L b17

427

L a236

L b21

428

L a236

L b22

429

L a236

L b26

430

L a236

L b28

431

L a236

L b30

432

L a236

L b31

433

L a236

L b35

434

L a236

L b37

435

L a236

L b38

436

L a236

L b39

437

L a236

L b40

438

L a236

L b41

439

L a236

L b42

440

L a236

L b43

441

L a236

L b44

442

L a236

L b45

443

L a236

L b71

444

L a236

L b72

445

L a236

L b79

446

L a236

L b80

447

L a236

L b81

448

L a236

L b99

449

L a236

L b112

450

L a236

L b151

451

L a236

L b153

452

L a236

L b164

453

L a236

L b166

454

L a236

L b209

455

L a236

L b287

456

L a236

L b299

457

L a237

L b1

458

L a237

L b3

459

L a237

L b4

460

L a237

L b8

461

L a237

L b10

462

L a237

L b12

463

L a237

L b13

464

L a237

L b17

465

L a237

L b21

466

L a237

L b22

467

L a237

L b26

468

L a237

L b28

469

L a237

L b30

470

L a237

L b31

471

L a237

L b35

472

L a237

L b37

473

L a237

L b38

474

L a237

L b39

475

L a237

L b40

476

L a237

L b41

477

L a237

L b42

478

L a237

L b43

479

L a237

L b44

480

L a237

L b45

481

L a237

L b71

482

L a237

L b72

483

L a237

L b79

484

L a237

L b80

485

L a237

L b81

486

L a237

L b99

487

L a237

L b112

488

L a237

L b151

489

L a237

L b153

490

L a237

L b164

491

L a237

L b166

492

L a237

L b209

493

L a237

L b287

494

L a237

L b299

495

L a238

L b1

496

L a238

L b3

497

L a238

L b4

498

L a238

L b8

499

L a238

L b10

500

L a238

L b12

501

L a238

L b13

502

L a238

L b17

503

L a238

L b21

504

L a238

L b22

505

L a238

L b26

506

L a238

L b28

507

L a238

L b30

508

L a238

L b31

509

L a238

L b35

510

L a238

L b37

511

L a238

L b38

512

L a238

L b39

513

L a238

L b40

514

L a238

L b41

515

L a238

L b42

516

L a238

L b43

517

L a238

L b44

518

L a238

L b45

519

L a238

L b71

520

L a238

L b72

521

L a238

L b79

522

L a238

L b80

523

L a238

L b81

524

L a238

L b99

525

L a238

L b112

526

L a238

L b151

527

L a238

L b153

528

L a238

L b164

529

L a238

L b166

530

L a238

L b209

531

L a238

L b287

532

L a238

L b299

533

L a239

L b1

534

L a239

L b3

535

L a239

L b4

536

L a239

L b8

537

L a239

L b10

538

L a239

L b12

539

L a239

L b13

540

L a239

L b17

541

L a239

L b21

542

L a239

L b22

543

L a239

L b26

544

L a239

L b28

545

L a239

L b30

546

L a239

L b31

547

L a239

L b35

548

L a239

L b37

549

L a239

L b38

550

L a239

L b39

551

L a239

L b40

552

L a239

L b41

553

L a239

L b42

554

L a239

L b43

555

L a239

L b44

556

L a239

L b45

557

L a239

L b71

558

L a239

L b72

559

L a239

L b79

560

L a239

L b80

561

L a239

L b81

562

L a239

L b99

563

L a239

L b112

564

L a239

L b151

565

L a239

L b153

566

L a239

L b164

567

L a239

L b166

568

L a239

L b209

569

L a239

L b287

570

L a239

L b299

571

L a245

L b1

572

L a245

L b3

573

L a245

L b4

574

L a245

L b8

575

L a245

L b10

576

L a245

L b12

577

L a245

L b13

578

L a245

L b17

579

L a245

L b21

580

L a245

L b22

581

L a245

L b26

582

L a245

L b28

583

L a245

L b30

584

L a245

L b31

585

L a245

L b35

586

L a245

L b37

587

L a245

L b38

588

L a245

L b39

589

L a245

L b40

590

L a245

L b41

591

L a245

L b42

592

L a245

L b43

593

L a245

L b44

594

L a245

L b45

595

L a245

L b71

596

L a245

L b72

597

L a245

L b79

598

L a245

L b80

599

L a245

L b81

600

L a245

L b99

601

L a245

L b112

602

L a245

L b151

603

L a245

L b153

604

L a245

L b164

605

L a245

L b166

606

L a245

L b209

607

L a245

L b287

608

L a245

L b299

609

L a250

L b1

610

L a250

L b3

611

L a250

L b4

612

L a250

L b8

613

L a250

L b10

614

L a250

L b12

615

L a250

L b13

616

L a250

L b17

617

L a250

L b21

618

L a250

L b22

619

L a250

L b26

620

L a250

L b28

621

L a250

L b30

622

L a250

L b31

623

L a250

L b35

624

L a250

L b37

625

L a250

L b38

626

L a250

L b39

627

L a250

L b40

628

L a250

L b41

629

L a250

L b42

630

L a250

L b43

631

L a250

L b44

632

L a250

L b45

633

L a250

L b71

634

L a250

L b72

635

L a250

L b79

636

L a250

L b80

637

L a250

L b81

638

L a250

L b99

639

L a250

L b112

640

L a250

L b151

641

L a250

L b153

642

L a250

L b164

643

L a250

L b166

644

L a250

L b209

645

L a250

L b287

646

L a250

L b299

647

L a251

L b1

648

L a251

L b3

649

L a251

L b4

650

L a251

L b8

651

L a251

L b10

652

L a251

L b12

653

L a251

L b13

654

L a251

L b17

655

L a251

L b21

656

L a251

L b22

657

L a251

L b26

658

L a251

L b28

659

L a251

L b30

660

L a251

L b31

661

L a251

L b35

662

L a251

L b37

663

L a251

L b38

664

L a251

L b39

665

L a251

L b40

666

L a251

L b41

667

L a251

L b42

668

L a251

L b43

669

L a251

L b44

670

L a251

L b45

671

L a251

L b71

672

L a251

L b72

673

L a251

L b79

674

L a251

L b80

675

L a251

L b81

676

L a251

L b99

677

L a251

L b112

678

L a251

L b151

679

L a251

L b153

680

L a251

L b164

681

L a251

L b166

682

L a251

L b209

683

L a251

L b287

684

L a251

L b299

685

L a252

L b1

686

L a252

L b3

687

L a252

L b4

688

L a252

L b8

689

L a252

L b10

690

L a252

L b12

691

L a252

L b13

692

L a252

L b17

693

L a252

L b21

694

L a252

L b22

695

L a252

L b26

696

L a252

L b28

697

L a252

L b30

698

L a252

L b31

699

L a252

L b35

700

L a252

L b37

701

L a252

L b38

702

L a252

L b39

703

L a252

L b40

704

L a252

L b41

705

L a252

L b42

706

L a252

L b43

707

L a252

L b44

708

L a252

L b45

709

L a252

L b71

710

L a252

L b72

711

L a252

L b79

712

L a252

L b80

713

L a252

L b81

714

L a252

L b99

715

L a252

L b112

716

L a252

L b151

717

L a252

L b153

718

L a252

L b164

719

L a252

L b166

720

L a252

L b209

721

L a252

L b287

722

L a252

L b299

723

L a253

L b1

724

L a253

L b3

725

L a253

L b4

726

L a253

L b8

727

L a253

L b10

728

L a253

L b12

729

L a253

L b13

730

L a253

L b17

731

L a253

L b21

732

L a253

L b22

733

L a253

L b26

734

L a253

L b28

735

L a253

L b30

736

L a253

L b31

737

L a253

L b35

738

L a253

L b37

739

L a253

L b38

740

L a253

L b39

741

L a253

L b40

742

L a253

L b41

743

L a253

L b42

744

L a253

L b43

745

L a253

L b44

746

L a253

L b45

747

L a253

L b71

748

L a253

L b72

749

L a253

L b79

750

L a253

L b80

751

L a253

L b81

752

L a253

L b99

753

L a253

L b112

754

L a253

L b151

755

L a253

L b153

756

L a253

L b164

757

L a253

L b166

758

L a253

L b209

759

L a253

L b287

760

L a253

L b299

761

L a259

L b1

762

L a259

L b3

763

L a259

L b4

764

L a259

L b8

765

L a259

L b10

766

L a259

L b12

767

L a259

L b13

768

L a259

L b17

769

L a259

L b21

770

L a259

L b22

771

L a259

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772

L a259

L b28

773

L a259

L b30

774

L a259

L b31

775

L a259

L b35

776

L a259

L b37

777

L a259

L b38

778

L a259

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779

L a259

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780

L a259

L b41

781

L a259

L b42

782

L a259

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783

L a259

L b44

784

L a259

L b45

785

L a259

L b71

786

L a259

L b72

787

L a259

L b79

788

L a259

L b80

789

L a259

L b81

790

L a259

L b99

791

L a259

L b112

792

L a259

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793

L a259

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794

L a259

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795

L a259

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796

L a259

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797

L a259

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798

L a259

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799

L a264

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800

L a264

L b3

801

L a264

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802

L a264

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803

L a264

L b10

804

L a264

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805

L a264

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806

L a264

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807

L a264

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808

L a264

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809

L a264

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810

L a264

L b28

811

L a264

L b30

812

L a264

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813

L a264

L b35

814

L a264

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815

L a264

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816

L a264

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817

L a264

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818

L a264

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819

L a264

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820

L a264

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821

L a264

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822

L a264

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823

L a264

L b71

824

L a264

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825

L a264

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826

L a264

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827

L a264

L b81

828

L a264

L b99

829

L a264

L b112

830

L a264

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831

L a264

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832

L a264

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833

L a264

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834

L a264

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835

L a264

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836

L a264

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837

L a269

L b1

838

L a269

L b3

839

L a269

L b4

840

L a269

L b8

841

L a269

L b10

842

L a269

L b12

843

L a269

L b13

844

L a269

L b17

845

L a269

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846

L a269

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847

L a269

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848

L a269

L b28

849

L a269

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850

L a269

L b31

851

L a269

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852

L a269

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853

L a269

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854

L a269

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855

L a269

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856

L a269

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857

L a269

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858

L a269

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859

L a269

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860

L a269

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861

L a269

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862

L a269

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863

L a269

L b79

864

L a269

L b80

865

L a269

L b81

866

L a269

L b99

867

L a269

L b112

868

L a269

L b151

869

L a269

L b153

870

L a269

L b164

871

L a269

L b166

872

L a269

L b209

873

L a269

L b287

874

L a269

L b299

875

L a274

L b1

876

L a274

L b3

877

L a274

L b4

878

L a274

L b8

879

L a274

L b10

880

L a274

L b12

881

L a274

L b13

882

L a274

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883

L a274

L b21

884

L a274

L b22

885

L a274

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886

L a274

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887

L a274

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888

L a274

L b31

889

L a274

L b35

890

L a274

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891

L a274

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892

L a274

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893

L a274

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894

L a274

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895

L a274

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896

L a274

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897

L a274

L b44

898

L a274

L b45

899

L a274

L b71

900

L a274

L b72

901

L a274

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902

L a274

L b80

903

L a274

L b81

904

L a274

L b99

905

L a274

L b112

906

L a274

L b151

907

L a274

L b153

908

L a274

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909

L a274

L b166

910

L a274

L b209

911

L a274

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912

L a274

L b299

913

L a287

L b1

914

L a287

L b3

915

L a287

L b4

916

L a287

L b8

917

L a287

L b10

918

L a287

L b12

919

L a287

L b13

920

L a287

L b17

921

L a287

L b21

922

L a287

L b22

923

L a287

L b26

924

L a287

L b28

925

L a287

L b30

926

L a287

L b31

927

L a287

L b35

928

L a287

L b37

929

L a287

L b38

930

L a287

L b39

931

L a287

L b40

932

L a287

L b41

933

L a287

L b42

934

L a287

L b43

935

L a287

L b44

936

L a287

L b45

937

L a287

L b71

938

L a287

L b72

939

L a287

L b79

940

L a287

L b80

941

L a287

L b81

942

L a287

L b99

943

L a287

L b112

944

L a287

L b151

945

L a287

L b153

946

L a287

L b164

947

L a287

L b166

948

L a287

L b209

949

L a287

L b287

950

L a287

L b299

951

L a289

L b1

952

L a289

L b3

953

L a289

L b4

954

L a289

L b8

955

L a289

L b10

956

L a289

L b12

957

L a289

L b13

958

L a289

L b17

959

L a289

L b21

960

L a289

L b22

961

L a289

L b26

962

L a289

L b28

963

L a289

L b30

964

L a289

L b31

965

L a289

L b35

966

L a289

L b37

967

L a289

L b38

968

L a289

L b39

969

L a289

L b40

970

L a289

L b41

971

L a289

L b42

972

L a289

L b43

973

L a289

L b44

974

L a289

L b45

975

L a289

L b71

976

L a289

L b72

977

L a289

L b79

978

L a289

L b80

979

L a289

L b81

980

L a289

L b99

981

L a289

L b112

982

L a289

L b151

983

L a289

L b153

984

L a289

L b164

985

L a289

L b166

986

L a289

L b209

987

L a289

L b287

988

L a289

L b299

989

L a290

L b1

990

L a290

L b3

991

L a290

L b4

992

L a290

L b8

993

L a290

L b10

994

L a290

L b12

995

L a290

L b13

996

L a290

L b17

997

L a290

L b21

998

L a290

L b22

999

L a290

L b26

1000

L a290

L b28

1001

L a290

L b30

1002

L a290

L b31

1003

L a290

L b35

1004

L a290

L b37

1005

L a290

L b38

1006

L a290

L b39

1007

L a290

L b40

1008

L a290

L b41

1009

L a290

L b42

1010

L a290

L b43

1011

L a290

L b44

1012

L a290

L b45

1013

L a290

L b71

1014

L a290

L b72

1015

L a290

L b79

1016

L a290

L b80

1017

L a290

L b81

1018

L a290

L b99

1019

L a290

L b112

1020

L a290

L b151

1021

L a290

L b153

1022

L a290

L b164

1023

L a290

L b166

1024

L a290

L b209

1025

L a290

L b287

1026

L a290

L b299

1027

L a297

L b1

1028

L a297

L b3

1029

L a297

L b4

1030

L a297

L b8

1031

L a297

L b10

1032

L a297

L b12

1033

L a297

L b13

1034

L a297

L b17

1035

L a297

L b21

1036

L a297

L b22

1037

L a297

L b26

1038

L a297

L b28

1039

L a297

L b30

1040

L a297

L b31

1041

L a297

L b35

1042

L a297

L b37

1043

L a297

L b38

1044

L a297

L b39

1045

L a297

L b40

1046

L a297

L b41

1047

L a297

L b42

1048

L a297

L b43

1049

L a297

L b44

1050

L a297

L b45

1051

L a297

L b71

1052

L a297

L b72

1053

L a297

L b79

1054

L a297

L b80

1055

L a297

L b81

1056

L a297

L b99

1057

L a297

L b112

1058

L a297

L b151

1059

L a297

L b153

1060

L a297

L b164

1061

L a297

L b166

1062

L a297

L b209

1063

L a297

L b287

1064

L a297

L b299

1065

L a299

L b1

1066

L a299

L b3

1067

L a299

L b4

1068

L a299

L b8

1069

L a299

L b10

1070

L a299

L b12

1071

L a299

L b13

1072

L a299

L b17

1073

L a299

L b21

1074

L a299

L b22

1075

L a299

L b26

1076

L a299

L b28

1077

L a299

L b30

1078

L a299

L b31

1079

L a299

L b35

1080

L a299

L b37

1081

L a299

L b38

1082

L a299

L b39

1083

L a299

L b40

1084

L a299

L b41

1085

L a299

L b42

1086

L a299

L b43

1087

L a299

L b44

1088

L a299

L b45

1089

L a299

L b71

1090

L a299

L b72

1091

L a299

L b79

1092

L a299

L b80

1093

L a299

L b81

1094

L a299

L b99

1095

L a299

L b112

1096

L a299

L b151

1097

L a299

L b153

1098

L a299

L b164

1099

L a299

L b166

1100

L a299

L b209

1101

L a299

L b287

1102

L a299

L b299

1179

L a327

L b1

1180

L a327

L b3

1181

L a327

L b4

1182

L a327

L b8

1183

L a327

L b10

1184

L a327

L b12

1185

L a327

L b13

1186

L a327

L b17

1187

L a327

L b21

1188

L a327

L b22

1189

L a327

L b26

1190

L a327

L b28

1191

L a327

L b30

1192

L a327

L b31

1193

L a327

L b35

1194

L a327

L b37

1195

L a327

L b38

1196

L a327

L b39

1197

L a327

L b40

1198

L a327

L b41

1199

L a327

L b42

1200

L a327

L b43

1201

L a327

L b44

1202

L a327

L b45

1203

L a327

L b71

1204

L a327

L b72

1205

L a327

L b79

1206

L a327

L b80

1207

L a327

L b81

1208

L a327

L b99

1209

L a327

L b112

1210

L a327

L b151

1211

L a327

L b153

1212

L a327

L b164

1213

L a327

L b166

1214

L a327

L b209

1215

L a327

L b287

1216

L a327

L b299

1217

L a329

L b1

1218

L a329

L b3

1219

L a329

L b4

1220

L a329

L b8

1221

L a329

L b10

1222

L a329

L b12

1223

L a329

L b13

1224

L a329

L b17

1225

L a329

L b21

1226

L a329

L b22

1227

L a329

L b26

1228

L a329

L b28

1229

L a329

L b30

1230

L a329

L b31

1231

L a329

L b35

1232

L a329

L b37

1233

L a329

L b38

1234

L a329

L b39

1235

L a329

L b40

1236

L a329

L b41

1237

L a329

L b42

1238

L a329

L b43

1239

L a329

L b44

1240

L a329

L b45

1241

L a329

L b71

1242

L a329

L b72

1243

L a329

L b79

1244

L a329

L b80

1245

L a329

L b81

1246

L a329

L b99

1247

L a329

L b112

1248

L a329

L b151

1249

L a329

L b153

1250

L a329

L b164

1251

L a329

L b166

1252

L a329

L b209

1253

L a329

L b287

1254

L a329

L b299

1255

L a330

L b1

1256

L a330

L b3

1257

L a330

L b4

1258

L a330

L b8

1259

L a330

L b10

1260

L a330

L b12

1261

L a330

L b13

1262

L a330

L b17

1263

L a330

L b21

1264

L a330

L b22

1265

L a330

L b26

1266

L a330

L b28

1267

L a330

L b30

1268

L a330

L b31

1269

L a330

L b35

1270

L a330

L b37

1271

L a330

L b38

1272

L a330

L b39

1273

L a330

L b40

1274

L a330

L b41

1275

L a330

L b42

1276

L a330

L b43

1277

L a330

L b44

1278

L a330

L b45

1279

L a330

L b71

1280

L a330

L b72

1281

L a330

L b79

1282

L a330

L b80

1283

L a330

L b81

1284

L a330

L b99

1285

L a330

L b112

1286

L a330

L b151

1287

L a330

L b153

1288

L a330

L b164

1289

L a330

L b166

1290

L a330

L b209

1291

L a330

L b287

1292

L a330

L b299

1293

L a331

L b1

1294

L a331

L b3

1295

L a331

L b4

1296

L a331

L b8

1297

L a331

L b10

1298

L a331

L b12

1299

L a331

L b13

1300

L a331

L b17

1301

L a331

L b21

1302

L a331

L b22

1303

L a331

L b26

1304

L a331

L b28

1305

L a331

L b30

1306

L a331

L b31

1307

L a331

L b35

1308

L a331

L b37

1309

L a331

L b38

1310

L a331

L b39

1311

L a331

L b40

1312

L a331

L b41

1313

L a331

L b42

1314

L a331

L b43

1315

L a331

L b44

1316

L a331

L b45

1317

L a331

L b71

1318

L a331

L b72

1319

L a331

L b79

1320

L a331

L b80

1321

L a331

L b81

1322

L a331

L b99

1323

L a331

L b112

1324

L a331

L b151

1325

L a331

L b153

1326

L a331

L b164

1327

L a331

L b166

1328

L a331

L b209

1329

L a331

L b287

1330

L a331

L b299

1331

L a336

L b1

1332

L a336

L b3

1333

L a336

L b4

1334

L a336

L b8

1335

L a336

L b10

1336

L a336

L b12

1337

L a336

L b13

1338

L a336

L b17

1339

L a336

L b21

1340

L a336

L b22

1341

L a336

L b26

1342

L a336

L b28

1343

L a336

L b30

1344

L a336

L b31

1345

L a336

L b35

1346

L a336

L b37

1347

L a336

L b38

1348

L a336

L b39

1349

L a336

L b40

1350

L a336

L b41

1351

L a336

L b42

1352

L a336

L b43

1353

L a336

L b44

1354

L a336

L b45

1355

L a336

L b71

1356

L a336

L b72

1357

L a336

L b79

1358

L a336

L b80

1359

L a336

L b81

1360

L a336

L b99

1361

L a336

L b112

1362

L a336

L b151

1363

L a336

L b153

1364

L a336

L b164

1365

L a336

L b166

1366

L a336

L b209

1367

L a336

L b287

1368

L a336

L b299

1369

L a381

L b1

1370

L a381

L b3

1371

L a381

L b4

1372

L a381

L b8

1373

L a381

L b10

1374

L a381

L b12

1375

L a381

L b13

1376

L a381

L b17

1377

L a381

L b21

1378

L a381

L b22

1379

L a381

L b26

1380

L a381

L b28

1381

L a381

L b30

1382

L a381

L b31

1383

L a381

L b35

1384

L a381

L b37

1385

L a381

L b38

1386

L a381

L b39

1387

L a381

L b40

1388

L a381

L b41

1389

L a381

L b42

1390

L a381

L b43

1391

L a381

L b44

1392

L a381

L b45

1393

L a381

L b71

1394

L a381

L b72

1395

L a381

L b79

1396

L a381

L b80

1397

L a381

L b81

1398

L a381

L b99

1399

L a381

L b112

1400

L a381

L b151

1401

L a381

L b153

1402

L a381

L b164

1403

L a381

L b166

1404

L a381

L b209

1405

L a381

L b287

1406

L a381

L b299

1407

L a391

L b1

1408

L a391

L b3

1409

L a391

L b4

1410

L a391

L b8

1411

L a391

L b10

1412

L a391

L b12

1413

L a391

L b13

1414

L a391

L b17

1415

L a391

L b21

1416

L a391

L b22

1417

L a391

L b26

1418

L a391

L b28

1419

L a391

L b30

1420

L a391

L b31

1421

L a391

L b35

1422

L a391

L b37

1423

L a391

L b38

1424

L a391

L b39

1425

L a391

L b40

1426

L a391

L b41

1427

L a391

L b42

1428

L a391

L b43

1429

L a391

L b44

1430

L a391

L b45

1431

L a391

L b71

1432

L a391

L b72

1433

L a391

L b79

1434

L a391

L b80

1435

L a391

L b81

1436

L a391

L b99

1437

L a391

L b112

1438

L a391

L b151

1439

L a391

L b153

1440

L a391

L b164

1441

L a391

L b166

1442

L a391

L b209

1443

L a391

L b287

1444

L a391

L b299

1445

L a403

L b1

1446

L a403

L b3

1447

L a403

L b4

1448

L a403

L b8

1449

L a403

L b10

1450

L a403

L b12

1451

L a403

L b13

1452

L a403

L b17

1453

L a403

L b21

1454

L a403

L b22

1455

L a403

L b26

1456

L a403

L b28

1457

L a403

L b30

1458

L a403

L b31

1459

L a403

L b35

1460

L a403

L b37

1461

L a403

L b38

1462

L a403

L b39

1463

L a403

L b40

1464

L a403

L b41

1465

L a403

L b42

1466

L a403

L b43

1467

L a403

L b44

1468

L a403

L b45

1469

L a403

L b71

1470

L a403

L b72

1471

L a403

L b79

1472

L a403

L b80

1473

L a403

L b81

1474

L a403

L b99

1475

L a403

L b112

1476

L a403

L b151

1477

L a403

L b153

1478

L a403

L b164

1479

L a403

L b166

1480

L a403

L b209

1481

L a403

L b287

1482

L a403

L b299

1483

L a413

L b1

1484

L a413

L b3

1485

L a413

L b4

1486

L a413

L b8

1487

L a413

L b10

1488

L a413

L b12

1489

L a413

L b13

1490

L a413

L b17

1491

L a413

L b21

1492

L a413

L b22

1493

L a413

L b26

1494

L a413

L b28

1495

L a413

L b30

1496

L a413

L b31

1497

L a413

L b35

1498

L a413

L b37

1499

L a413

L b38

1500

L a413

L b39

1501

L a413

L b40

1502

L a413

L b41

1503

L a413

L b42

1504

L a413

L b43

1505

L a413

L b44

1506

L a413

L b45

1507

L a413

L b71

1508

L a413

L b72

1509

L a413

L b79

1510

L a413

L b80

1511

L a413

L b81

1512

L a413

L b99

1513

L a413

L b112

1514

L a413

L b151

1515

L a413

L b153

1516

L a413

L b164

1517

L a413

L b166

1518

L a413

L b209

1519

L a413

L b287

1520

L a413

L b299

1521

L a435

L b1

1522

L a435

L b3

1523

L a435

L b4

1524

L a435

L b8

1525

L a435

L b10

1526

L a435

L b12

1527

L a435

L b13

1528

L a435

L b17

1529

L a435

L b21

1530

L a435

L b22

1531

L a435

L b26

1532

L a435

L b28

1533

L a435

L b30

1534

L a435

L b31

1535

L a435

L b35

1536

L a435

L b37

1537

L a435

L b38

1538

L a435

L b39

1539

L a435

L b40

1540

L a435

L b41

1541

L a435

L b42

1542

L a435

L b43

1543

L a435

L b44

1544

L a435

L b45

1545

L a435

L b71

1546

L a435

L b72

1547

L a435

L b79

1548

L a435

L b80

1549

L a435

L b81

1550

L a435

L b99

1551

L a435

L b112

1552

L a435

L b151

1553

L a435

L b153

1554

L a435

L b164

1555

L a435

L b166

1556

L a435

L b209

1557

L a435

L b287

1558

L a435

L b299

1559

L a446

L b1

1560

L a446

L b3

1561

L a446

L b4

1562

L a446

L b8

1563

L a446

L b10

1564

L a446

L b12

1565

L a446

L b13

1566

L a446

L b17

1567

L a446

L b21

1568

L a446

L b22

1569

L a446

L b26

1570

L a446

L b28

1571

L a446

L b30

1572

L a446

L b31

1573

L a446

L b35

1574

L a446

L b37

1575

L a446

L b38

1576

L a446

L b39

1577

L a446

L b40

1578

L a446

L b41

1579

L a446

L b42

1580

L a446

L b43

1581

L a446

L b44

1582

L a446

L b45

1583

L a446

L b71

1584

L a446

L b72

1585

L a446

L b79

1586

L a446

L b80

1587

L a446

L b81

1588

L a446

L b99

1589

L a446

L b112

1590

L a446

L b151

1591

L a446

L b153

1592

L a446

L b164

1593

L a446

L b166

1594

L a446

L b209

1595

L a446

L b287

1596

L a446

L b299

1597

L a466

L b1

1598

L a466

L b3

1599

L a466

L b4

1600

L a466

L b8

1601

L a466

L b10

1602

L a466

L b12

1603

L a466

L b13

1604

L a466

L b17

1605

L a466

L b21

1606

L a466

L b22

1607

L a466

L b26

1608

L a466

L b28

1609

L a466

L b30

1610

L a466

L b31

1611

L a466

L b35

1612

L a466

L b37

1613

L a466

L b38

1614

L a466

L b39

1615

L a466

L b40

1616

L a466

L b41

1617

L a466

L b42

1618

L a466

L b43

1619

L a466

L b44

1620

L a466

L b45

1621

L a466

L b71

1622

L a466

L b72

1623

L a466

L b79

1624

L a466

L b80

1625

L a466

L b81

1626

L a466

L b99

1627

L a466

L b112

1628

L a466

L b151

1629

L a466

L b153

1630

L a466

L b164

1631

L a466

L b166

1632

L a466

L b209

1633

L a466

L b287

1634

L a466

L b299

1635

L a518

L b1

1636

L a518

L b3

1637

L a518

L b4

1638

L a518

L b8

1639

L a518

L b10

1640

L a518

L b12

1641

L a518

L b13

1642

L a518

L b17

1643

L a518

L b21

1644

L a518

L b22

1645

L a518

L b26

1646

L a518

L b28

1647

L a518

L b30

1648

L a518

L b31

1649

L a518

L b35

1650

L a518

L b37

1651

L a518

L b38

1652

L a518

L b39

1653

L a518

L b40

1654

L a518

L b41

1655

L a518

L b42

1656

L a518

L b43

1657

L a518

L b44

1658

L a518

L b45

1659

L a518

L b71

1660

L a518

L b72

1661

L a518

L b79

1662

L a518

L b80

1663

L a518

L b81

1664

L a518

L b99

1665

L a518

L b112

1666

L a518

L b151

1667

L a518

L b153

1668

L a518

L b164

1669

L a518

L b166

1670

L a518

L b209

1671

L a518

L b287

1672

L a518

L b299

1673

L a519

L b1

1674

L a519

L b3

1675

L a519

L b4

1676

L a519

L b8

1677

L a519

L b10

1678

L a519

L b12

1679

L a519

L b13

1680

L a519

L b17

1681

L a519

L b21

1682

L a519

L b22

1683

L a519

L b26

1684

L a519

L b28

1685

L a519

L b30

1686

L a519

L b31

1687

L a519

L b35

1688

L a519

L b37

1689

L a519

L b38

1690

L a519

L b39

1691

L a519

L b40

1692

L a519

L b41

1693

L a519

L b42

1694

L a519

L b43

1695

L a519

L b44

1696

L a519

L b45

1697

L a519

L b71

1698

L a519

L b72

1699

L a519

L b79

1700

L a519

L b80

1701

L a519

L b81

1702

L a519

L b99

1703

L a519

L b112

1704

L a519

L b151

1705

L a519

L b153

1706

L a519

L b164

1707

L a519

L b166

1708

L a519

L b209

1709

L a519

L b287

1710

L a519

L b299

1711

L a525

L b1

1712

L a525

L b3

1713

L a525

L b4

1714

L a525

L b8

1715

L a525

L b10

1716

L a525

L b12

1717

L a525

L b13

1718

L a525

L b17

1719

L a525

L b21

1720

L a525

L b22

1721

L a525

L b26

1722

L a525

L b28

1723

L a525

L b30

1724

L a525

L b31

1725

L a525

L b35

1726

L a525

L b37

1727

L a525

L b38

1728

L a525

L b39

1729

L a525

L b40

1730

L a525

L b41

1731

L a525

L b42

1732

L a525

L b43

1733

L a525

L b44

1734

L a525

L b45

1735

L a525

L b71

1736

L a525

L b72

1737

L a525

L b79

1738

L a525

L b80

1739

L a525

L b81

1740

L a525

L b99

1741

L a525

L b112

1742

L a525

L b151

1743

L a525

L b153

1744

L a525

L b164

1745

L a525

L b166

1746

L a525

L b209

1747

L a525

L b287

1748

L a525

L b299

1749

L a562

L b1

1750

L a562

L b3

1751

L a562

L b4

1752

L a562

L b8

1753

L a562

L b10

1754

L a562

L b12

1755

L a562

L b13

1756

L a562

L b17

1757

L a562

L b21

1758

L a562

L b22

1759

L a562

L b26

1760

L a562

L b28

1761

L a562

L b30

1762

L a562

L b31

1763

L a562

L b35

1764

L a562

L b37

1765

L a562

L b38

1766

L a562

L b39

1767

L a562

L b40

1768

L a562

L b41

1769

L a562

L b42

1770

L a562

L b43

1771

L a562

L b44

1772

L a562

L b45

1773

L a562

L b71

1774

L a562

L b72

1775

L a562

L b79

1776

L a562

L b80

1777

L a562

L b81

1778

L a562

L b99

1779

L a562

L b112

1780

L a562

L b151

1781

L a562

L b153

1782

L a562

L b164

1783

L a562

L b166

1784

L a562

L b209

1785

L a562

L b287

1786

L a562

L b299

1787

L a575

L b1

1788

L a575

L b3

1789

L a575

L b4

1790

L a575

L b8

1791

L a575

L b10

1792

L a575

L b12

1793

L a575

L b13

1794

L a575

L b17

1795

L a575

L b21

1796

L a575

L b22

1797

L a575

L b26

1798

L a575

L b28

1799

L a575

L b30

1800

L a575

L b31

1801

L a575

L b35

1802

L a575

L b37

1803

L a575

L b38

1804

L a575

L b39

1805

L a575

L b40

1806

L a575

L b41

1807

L a575

L b42

1808

L a575

L b43

1809

L a575

L b44

1810

L a575

L b45

1811

L a575

L b71

1812

L a575

L b72

1813

L a575

L b79

1814

L a575

L b80

1815

L a575

L b81

1816

L a575

L b99

1817

L a575

L b112

1818

L a575

L b151

1819

L a575

L b153

1820

L a575

L b164

1821

L a575

L b166

1822

L a575

L b209

1823

L a575

L b287

1824

L a575

L b299

1863

L a597

L b1

1864

L a597

L b3

1865

L a597

L b4

1866

L a597

L b8

1867

L a597

L b10

1868

L a597

L b12

1869

L a597

L b13

1870

L a597

L b17

1871

L a597

L b21

1872

L a597

L b22

1873

L a597

L b26

1874

L a597

L b28

1875

L a597

L b30

1876

L a597

L b31

1877

L a597

L b35

1878

L a597

L b37

1879

L a597

L b38

1880

L a597

L b39

1881

L a597

L b40

1882

L a597

L b41

1883

L a597

L b42

1884

L a597

L b43

1885

L a597

L b44

1886

L a597

L b45

1887

L a597

L b71

1888

L a597

L b72

1889

L a597

L b79

1890

L a597

L b80

1891

L a597

L b81

1892

L a597

L b99

1893

L a597

L b112

1894

L a597

L b151

1895

L a597

L b153

1896

L a597

L b164

1897

L a597

L b166

1898

L a597

L b209

1899

L a597

L b287

1900

L a597

L b299.

10 . The metal complex of claim 1 , wherein the metal complex is Ir(L a ) m (L b ) 3-m and has a structure represented by Formula 3:

wherein,

m is selected from 1, 2 or 3; when m is selected from 1, two L b are identical or different;

when m is selected from 2 or 3, a plurality of L a are identical or different;

Y 1 to Y 4 are, at each occurrence identically or differently, selected from CR y or N;

X is selected from the group consisting of O, S, Se, NR′, CR′R′, SiR′R′, and GeR′R′; when two R′ are present, the two R′ are identical or different;

X 3 to X 7 are, at each occurrence identically or differently, selected from CR x or N;

at least one of X 3 to X 7 is CR x , wherein the R x is a cyano group or fluorine;

A has a structure represented by Formula 2:

wherein a is selected from 1;

A 1 is, at each occurrence identically or differently, selected from the group consisting of the following groups unsubstituted or substituted by one or at least two R a1 : alkylene having 1 to 20 carbon atoms, heteroalkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 20 carbon atoms, heterocyclene having 3 to 20 ring atoms, phenylene and heteroarylene having 5 to 6 ring atoms, and combinations thereof;

A 2 is, at each occurrence identically or differently, selected from the group consisting of the following groups unsubstituted or substituted by one or at least two R a2 : cycloalkylene having 3 to 20 carbon atoms, heterocyclene having 3 to 20 ring atoms, and combinations thereof;

R′, R x , R y , R a1 , R a2 , R a3 , and R 1 to R 8 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

adjacent substituents R 1 to R 8 can be optionally joined to form a ring;

adjacent substituents R′, R x , R y , R a2 , R a3 can be optionally joined to form a ring;

the length of A is at least 6.7 Å;

“*” represents a position where A is attached;

when A 1 is, at each occurrence identically or differently, selected from phenylene unsubstituted or substituted by one or at least two R a1 or heteroarylene having 5 to 6 ring atoms unsubstituted or substituted by one or at least two R a1 , A 2 and R a1 need to satisfy the following conditions:

1) A 2 that is directly attached to A 1 is, at each occurrence identically or differently, selected from the group consisting of: cycloalkylene having 3 to 20 carbon atoms unsubstituted or substituted by one or at least two R a2 , heterocyclene having 3 to 20 ring atoms unsubstituted or substituted by one or at least two R a2 , and combinations thereof; and

2) R a1 is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

11 . The metal complex of claim 10 , wherein X 3 to X 7 are, at each occurrence identically or differently, selected from CR x ; and/or Y 1 to Y 4 are, at each occurrence identically or differently, selected from CR y .

12 . The metal complex of claim 10 , wherein at least one of X 3 to X 7 is N, and/or at least one of Y 1 to Y 4 is N.

13 . The metal complex of claim 10 , wherein at least one of X 3 to X 7 is CR x , wherein the R x is cyano or fluorine; remaining R x are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, a cyano group, and combinations thereof.

14 . The metal complex of claim 10 , wherein R y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof.

15 . The metal complex of claim 10 , wherein at least one or at least two of R 5 to R 8 is (are), at each occurrence identically or differently, selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms or combinations thereof, and the total number of carbon atoms in all R 5 to R 8 is at least 4.

16 . The metal complex of claim 10 , wherein at least one or at least two or at least three or all of R 2 , R 3 , R 6 , and R 7 is (are) selected from the group consisting of: deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

17 . The metal complex of claim 10 , wherein X 7 is CR x , wherein the R x is cyano or fluorine; remaining R x are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, and combinations thereof.

18 . The metal complex of claim 10 , wherein at least one R y is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.

19 . The metal complex of claim 1 , wherein X is selected from O or S.

20 . The metal complex of claim 1 , wherein R a1 is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 4 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a hydroxyl group, a sulfanyl group, and combinations thereof.

21 . The metal complex of claim 1 , wherein R a2 and R a3 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a hydroxyl group, a sulfanyl group, and combinations thereof.

22 . The metal complex of claim 1 , wherein A is, at each occurrence identically or differently, selected from the group consisting of:

and combinations thereof;

optionally, hydrogen in the above groups can be partially or fully substituted with deuterium; wherein “*” represents a position where A is attached.

23 . An electroluminescent device, comprising:

an anode,

a cathode, and

an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex of claim 1 .

24 . The electroluminescent device of claim 23 , wherein the organic layer comprising the metal complex is an emissive layer.

25 . The electroluminescent device of claim 24 , wherein the electroluminescent device emits green light or white light.

26 . The electroluminescent device of claim 24 , wherein the emissive layer comprises a first host compound;

the emissive layer further comprises a second host compound;

the first host compound and/or the second host compound comprise at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

27 . The electroluminescent device of claim 26 , wherein the first host compound has a structure represented by Formula 4:

wherein,

E 1 to E 6 are, at each occurrence identically or differently, selected from C, CR e or N, at least two of E 1 to E 6 are N, and at least one of E 1 to E 6 is C and is attached to Formula A:

wherein,

Q is, at each occurrence identically or differently, selected from the group consisting of O, S, Se, N, NR″, CR″R″, SiR “R”, GeR “R”, and R′″C═CR″; when two R″ are present, the two R″ can be identical or different;

p is 0 or 1; r is 0 or 1;

when Q is selected from N, p is 0, and r is 1;

when Q is selected from the group consisting of O, S, Se, NR″, CR″R″, SiR′″R′″, GeR′″R′″, and R′″C═CR′″, p is 1, and r is 0;

L is, at each occurrence identically or differently, selected from a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted arylene having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms or combinations thereof;

Q 1 to Q 8 are, at each occurrence identically or differently, selected from C, CR q or N;

R e , R′″, and R q are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

“*” represents a position where Formula A is attached to Formula 4;

adjacent substituents R e , R′″, R q can be optionally joined to form a ring.

28 . The electroluminescent device of claim 27 , wherein E 1 to E 6 are, at each occurrence identically or differently, selected from C, CR e or N; wherein three of E 1 to E 6 are N, and at least one of E 1 to E 6 is CR e wherein the R e is, at each occurrence identically or differently, selected from the group consisting of: substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; and/or

Q is, at each occurrence identically or differently, selected from O, S, N or NR′″; and/or

R′″ is, at each occurrence identically or differently, selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms or combinations thereof; and/or

at least one or at least two of Q 1 to Q 8 is (are) selected from CR q , wherein the R q is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 carbon atoms or combinations thereof; and/or

L is, at each occurrence identically or differently, selected from a single bond, substituted or unsubstituted arylene having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms or combinations thereof.

29 . The electroluminescent device of claim 27 , wherein the first host compound is selected from the group consisting of:

30 . The electroluminescent device of claim 26 , wherein the second host compound has a structure represented by Formula 5:

wherein,

L x is, at each occurrence identically or differently, selected from a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted arylene having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms or combinations thereof;

V is, at each occurrence identically or differently, selected from C, CR v or N, and at least one of V is C and is attached to L x ;

U is, at each occurrence identically or differently, selected from C, CR u or N, and at least one of U is C and is attached to L x ;

R v and R u are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted alkynyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermanyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

Ar 6 is, at each occurrence identically or differently, selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms or combinations thereof;

adjacent substituents R v and R u can be optionally joined to form a ring;

the second host compound has a structure represented by one of Formula 5-a to Formula 5-j:

31 . The electroluminescent device of claim 30 , wherein the second host compound is selected from the group consisting of:

32 . The electroluminescent device of claim 26 , wherein the metal complex is doped in the first host compound and the second host compound, and

the weight of the metal complex accounts for 3% to 13% of the total weight of the emissive layer.

33 . A compound composition, comprising the metal complex of claim 1 .

34 . The metal complex of claim 1 , wherein A 1 is, at each occurrence identically or differently, selected from phenylene unsubstituted or substituted by one or at least two R a1 ; A 2 is, at each occurrence identically or differently, selected from cycloalkylene having 5 to 12 ring carbon atoms unsubstituted or substituted by one or at least two R a2 , heterocyclene unsubstituted or substituted by one or at least two R a2 and having 5 to 12 ring atoms or combinations thereof.

35 . The metal complex of claim 1 , wherein A 1 is, at each occurrence identically or differently, selected from the group consisting of the following groups unsubstituted or substituted by one or at least two R a1 : cycloalkylene having 3 to 10 carbon atoms and heterocyclene having 3 to 10 ring atoms, and combinations thereof; A 2 is, at each occurrence identically or differently, selected from following groups unsubstituted or substituted by one or at least two R a2 : cycloalkylene having 3 to 10 carbon atoms, heterocyclene having 3 to 10 ring atoms, and combinations thereof.

36 . The metal complex of claim 1 , wherein R a1 is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclohexyl, trimethylsilyl, and combinations thereof.

37 . The metal complex of claim 1 , wherein R a2 and R a3 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated t-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, and combinations thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2022
From: WANG, ZHEN; LI, HONGBO; SANG, MING; CAI, WEI; KWONG, CHI YUEN RAYMOND; XIA, CHUANJUN
To: BEIJING SUMMER SPROUT TECHNOLOGY CO., LTD.
Reel/Frame 059575/0638 →
Priority Claims (1)
CN 202110389568.7 · Apr 14, 2021 · national
Continuity (1)
Related Publication 20220372055A1 · Nov 24, 2022
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