IP Library › Granted Patent US 12,552,986
Granted Patent B2
US 12,552,986 · App. 17/881,372 · Granted Feb 17, 2026

Organic electroluminescent materials and devices

Inventors: Jui-Yi Tsai (Newtown, PA); Zhiqiang Ji (Hillsborough, NJ); Alexey Borisovich Dyatkin (Ambler, PA); Chuanjun Xia (Yardley, PA); Chun Lin (Yardley, PA); Lichang Zeng (Lawrenceville, NJ); Walter Yeager (Yardley, PA)
Assignee: UNIVERSAL DISPLAY CORPORATION
C09K11/06C07F15/0033C09K11/025H10K85/342H10K85/622H10K85/654H10K85/657H10K85/6574H10K85/6576C09K2211/1029C09K2211/1033C09K2211/185H10K50/11H10K50/15H10K50/16H10K2101/10H10K2101/90
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Quick Facts
Patent No.
US 12,552,986
App. No.
17/881,372
Granted
Feb 17, 2026
Kind
B2
Abstract

Iridium complexes comprising three different bidentate ligands and their use in OLEDs to enhance the device efficiency and lifetime are disclosed. The complexes have a structure of the formula Ir(L A )(L B )(L C ), where ligand L A is selected from a variety of structures, ligand L B has the structure and L C has the structure In these structures rings A, B, C, and D are each independently a 5 or 6-membered carbocyclic or heterocyclic ring; R 1 , R 2 , R 3 , R A , R B , R C , and R D can be any of a variety of substituents, and Z 1 and Z 2 are each independently C or N.

Claims (9249)

1 . A compound having a formula Ir(L A )(L B )(L C ) selected from

wherein L A is the ligand with substituents R 1 , R 2 , and R 3 ;

wherein L B is the ligand with substituents R A1 , R A2 , and R B ;

wherein L C is the ligand with substituents R C and R D ;

wherein R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D each independently represents mono, to a maximum possible number of substitutions, or no substitution;

wherein L A , L B , and L C are different from each other, and can be connected to each other to form multidentate ligand;

wherein R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein any two or more substituents among R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D are optionally joined or fused into a ring; and

wherein at least one of the following is true:

(i) at least one R 1 , R 2 , R 3 , R A , R A2 , R B , R C , or R D comprises a moiety selected from the group consisting of heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof; or

(ii) an R B is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, and (a) the R B is joined with an adjacent R B that together with the ring coordinated to the Ir atom forms a dibenzofuran or aza-dibenzofuran moiety, or (b) at least one R A1 , R A2 , or R B is a partially or fully deuterated alkyl or partially or fully fluorinated alkyl.

2 . The compound of claim 1 , wherein at least two of R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , or R D are independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.

3 . The compound of claim 1 , wherein at least one of L A , L B , and L C , is selected from the group consisting of:

where i in Ai is 1 to 212 and the substituents in L a Ai , L c Ai , and L d Ai are defined as,

L a Ai

L c Ai ,

and

L d Ai ,

where i

is

R 1a

R 1b

R 2

R 3a

R 3b

R 3c

1.

H

H

H

H

H

H

2.

H

CH3

H

H

H

H

3.

H

CD3

H

H

H

H

4.

H

C2H5

H

H

H

H

5.

H

CD2CH3

H

H

H

H

6.

H

CHMe2

H

H

H

H

7.

H

CDMe2

H

H

H

H

8.

H

H

H

H

H

9.

H

H

H

H

H

10.

H

H

H

H

H

11.

H

H

H

H

H

12.

H

H

H

H

H

13.

H

H

H

H

H

14.

H

H

H

H

H

15.

H

H

H

H

H

16.

H

H

H

H

H

17.

H

CH2CMe3

H

H

H

H

18.

H

CD2CMe3

H

H

H

H

19.

H

H

H

H

H

20.

H

H

H

H

H

21.

CH3

H

H

H

H

H

22.

CD3

H

H

H

H

H

23.

C2H5

H

H

H

H

H

24.

CD2CH3

H

H

H

H

H

25.

CHMe2

H

H

H

H

H

26.

CDMe2

H

H

H

H

H

27.

H

H

H

H

H

28.

H

H

H

H

H

29.

H

H

H

H

H

30.

H

H

H

H

H

31.

H

H

H

H

H

32.

H

H

H

H

H

33.

H

H

H

H

H

34.

H

H

H

H

H

35.

H

H

H

H

H

36.

CH2CMe3

H

H

H

H

H

37.

CD2CMe3

H

H

H

H

H

38.

H

H

H

H

H

39.

H

H

H

H

H

40.

CD3

CH3

H

H

H

H

41.

CD3

CD3

H

H

H

H

42.

CD3

C2H5

H

H

H

H

43.

CD3

CD2CH3

H

H

H

H

44.

CD3

CHMe2

H

H

H

H

45.

CD3

CDMe2

H

H

H

H

46.

CD3

H

H

H

H

47.

CD3

H

H

H

H

48.

CD3

H

H

H

H

49.

CD3

H

H

H

H

50.

CD3

H

H

H

H

51.

CD3

H

H

H

H

52.

CD3

H

H

H

H

53.

CD3

H

H

H

H

54.

CD3

H

H

H

H

55.

CD3

CH2CMe3

H

H

H

H

56.

CD3

CD2CMe3

H

H

H

H

57.

CH2CH3

CD3

H

H

H

H

58.

CD2CD3

CD3

H

H

H

H

59.

C2H5

CD3

H

H

H

H

60.

CD2CH3

CD2CD3

H

H

H

H

61.

CHMe2

CD3

H

H

H

H

62.

CDMe2

CD3

H

H

H

H

63.

CD3

H

H

H

H

64.

CD3

H

H

H

H

65.

CD3

H

H

H

H

66.

CD3

H

H

H

H

67.

CD3

H

H

H

H

68.

CD3

H

H

H

H

69.

CD3

H

H

H

H

70.

CD3

H

H

H

H

71.

CD3

H

H

H

H

72.

CH2CMe3

CD3

H

H

H

H

73.

CD2CMe3

CD3

H

H

H

H

74.

H

H

CD3

H

H

H

75.

H

CH3

CD3

H

H

H

76.

H

CD3

CD3

H

H

H

77.

H

C2H5

CD3

H

H

H

78.

H

CD2CH3

CD3

H

H

H

79.

H

CHMe2

CD3

H

H

H

80.

H

CDMe2

CD3

H

H

H

81.

H

CD3

H

H

H

82.

H

CD3

H

H

H

83.

H

CD3

H

H

H

84.

H

CD3

H

H

H

85.

H

CD3

H

H

H

86.

H

CD3

H

H

H

87.

H

CD3

H

H

H

88.

H

1-Ad

CD3

H

H

H

89.

H

CD3

H

H

H

90.

H

CH2CMe3

CD3

H

H

H

91.

H

CD2CMe3

CD3

H

H

H

92.

H

CD3

H

H

H

93.

H

CD3

H

H

H

94.

H

2-Ad

CD3

H

H

H

95.

H

H

CD3

H

H

CD3

96.

H

CH3

CD3

H

H

CD3

97.

H

CD3

CD3

H

H

CD3

98.

H

C2H5

CD3

H

H

CD3

99.

H

CD2CH3

CD3

H

H

CD3

100.

H

CHMe2

CD3

H

H

CD3

101.

H

CDMe2

CD3

H

H

CD3

102.

H

CD3

H

H

CD3

103.

H

CD3

H

H

CD3

104.

H

CD3

H

H

CD3

105.

H

CD3

H

H

CD3

106.

H

CD3

H

H

CD3

107.

H

CD3

H

H

CD3

108.

H

CD3

H

H

CD3

109.

H

1-Ad

CD3

H

H

CD3

110.

H

CD3

H

H

CD3

111.

H

CH2CMe3

CD3

H

H

CD3

112.

H

CD2CMe3

CD3

H

H

CD3

113.

H

CD3

H

H

CD3

114.

H

CD3

H

H

CD3

115.

H

2-Ad

CD3

H

H

H

116.

H

H

CD3

H

H

H

117.

H

CH3

CD3

H

H

H

118.

H

CD3

CD3

H

H

H

119.

H

C2H5

CD3

H

H

H

120.

H

CD2CH3

CD3

H

H

H

121.

H

CHMe2

CD3

H

H

H

122.

H

CDMe2

CD3

H

H

H

123.

H

CD3

H

H

H

124.

H

CD3

H

H

H

125.

H

CD3

H

H

H

126.

H

CD3

H

H

H

127.

H

CD3

H

H

H

128.

H

CD3

H

H

H

129.

H

CD3

H

H

H

130.

H

1-Ad

CD3

H

H

H

131.

H

CD3

H

H

H

132.

H

CH2CMe3

CD3

H

H

H

133.

H

CD2CMe3

CD3

H

H

H

134.

H

CD3

H

H

H

135.

H

CD3

H

H

H

136.

H

2-Ad

CD3

H

H

H

137.

H

H

H

H

CD3

H

138.

H

CH3

H

H

CD3

H

139.

H

CD3

H

H

CD3

H

140.

H

C2H5

H

H

CD3

H

141.

H

CD2CH3

H

H

CD3

H

142.

H

CHMe2

H

H

CD3

H

143.

H

CDMe2

H

H

CD3

H

144.

H

H

H

CD3

H

145.

H

H

H

CD3

H

146.

H

H

H

CD3

H

147.

H

H

H

CD3

H

148.

H

H

H

CD3

H

149.

H

H

H

CD3

H

150.

H

H

H

CD3

H

151.

H

H

H

CD3

H

152.

H

H

H

CD3

H

153.

H

CH2CMe3

H

H

CD3

H

154.

H

CD2CMe3

H

H

CD3

H

155.

H

H

H

CD3

H

156.

H

H

H

CD3

H

157.

H

H

H

CD3

H

H

158.

H

CH3

H

CD3

H

H

159.

H

CD3

H

CD3

H

H

160.

H

C2H5

H

CD3

H

H

161.

H

CD2CH3

H

CD3

H

H

162.

H

CHMe2

H

CD3

H

H

163.

H

CDMe2

H

CD3

H

H

164.

H

H

CD3

H

H

165.

H

H

CD3

H

H

166.

H

H

CD3

H

H

167.

H

H

CD3

H

H

168.

H

H

CD3

H

H

169.

H

H

CD3

H

H

170.

H

H

CD3

H

H

171.

H

H

CD3

H

H

172.

H

H

CD3

H

H

173.

H

CH2CMe3

H

CD3

H

H

174.

H

CD2CMe3

H

CD3

H

H

175.

H

H

CD3

H

H

176.

H

H

CD3

H

H

177.

CD3

Ph

H

H

H

H

178.

CD3

H

H

H

H

179.

CD3

H

H

H

H

180.

CD3

H

H

H

H

181.

H

Ph

H

H

H

H

182.

H

H

H

H

H

183.

H

H

H

H

H

184.

H

H

H

H

H

185.

CD3

Ph

CD3

H

H

H

186.

CD3

CD3

H

H

H

187.

CD3

CD3

H

H

H

188.

CD3

CD3

H

H

H

189.

H

Ph

CD3

H

H

H

190.

H

CD3

H

H

H

191.

H

CD3

H

H

H

192.

H

CD3

H

H

H

193.

H

H

H

H

H

H

194.

H

CH3

H

H

H

H

195.

H

CD3

H

H

H

H

196.

H

C2H5

H

H

H

H

197.

H

CD2CH3

H

H

H

H

198.

H

CHMe2

H

H

H

H

199.

H

CDMe2

H

H

H

H

200.

H

H

H

H

H

201.

H

H

H

H

H

202.

H

H

H

H

H

203.

H

H

H

H

H

204.

H

H

H

H

H

205.

H

H

H

H

H

206.

H

H

H

H

H

207.

H

H

H

H

H

208.

H

H

H

H

H

209.

CD3

CD3

H

H

CD3

H

210.

H

CD3

H

CD3

H

CD3

211.

CD3

H

CD3

H

H

H

212.

CD3

H

CD3

H

H

and L i , wherein L i is

wherein for each i from 1 to 1462, R B1 , R B2 , R B3 , and R B4 are defined as follows for each i:

i in Li

R B1

R B2

R B3

R B4

R B5

1.

H

H

H

H

H

2.

CH 3

H

H

H

H

3.

H

CH 3

H

H

H

4.

H

H

CH 3

H

H

5.

CH 3

CH 3

H

CH 3

H

6.

CH 3

H

CH 3

H

H

7.

CH 3

H

H

CH 3

H

8.

H

CH 3

CH 3

H

H

9.

H

CH 3

H

CH 3

H

10.

H

H

CH 3

CH 3

H

11.

CH 3

CH 3

CH 3

H

H

12.

CH 3

CH 3

H

CH 3

H

13.

CH 3

H

CH 3

CH 3

H

14.

H

CH 3

CH 3

CH 3

H

15.

CH 3

CH 3

CH 3

CH 3

H

16.

CH 2 CH 3

H

H

H

H

17.

CH 2 CH 3

CH 3

H

CH 3

H

18.

CH 2 CH 3

H

CH 3

H

H

19.

CH 2 CH 3

H

H

CH 3

H

20.

CH 2 CH 3

CH 3

CH 3

H

H

21.

CH 2 CH 3

CH 3

H

CH 3

H

22.

CH 2 CH 3

H

CH 3

CH 3

H

23.

CH 2 CH 3

CH 3

CH 3

CH 3

H

24.

H

CH 2 CH 3

H

H

H

25.

CH 3

CH 2 CH 3

H

CH 3

H

26.

H

CH 2 CH 3

CH 3

H

H

27.

H

CH 2 CH 3

H

CH 3

H

28.

CH 3

CH 2 CH 3

CH 3

H

H

29.

CH 3

CH 2 CH 3

H

CH 3

H

30.

H

CH 2 CH 3

CH 3

CH 3

H

31.

CH 3

CH 2 CH 3

CH 3

CH 3

H

32.

H

H

CH 2 CH 3

H

H

33.

CH 3

H

CH 2 CH 3

H

H

34.

H

CH 3

CH 2 CH 3

H

H

35.

H

H

CH 2 CH 3

CH 3

H

36.

CH 3

CH 3

CH 2 CH 3

H

H

37.

CH 3

H

CH 2 CH 3

CH 3

H

38.

H

CH 3

CH 2 CH 3

CH 3

H

39.

CH 3

CH 3

CH 2 CH 3

CH 3

H

40.

CH(CH 3 ) 2

H

H

H

H

41.

CH(CH 3 ) 2

CH 3

H

CH 3

H

42.

CH(CH 3 ) 2

H

CH 3

H

H

43.

CH(CH 3 ) 2

H

H

CH 3

H

44.

CH(CH 3 ) 2

CH 3

CH 3

H

H

45.

CH(CH 3 ) 2

CH 3

H

CH 3

H

46.

CH(CH 3 ) 2

H

CH 3

CH 3

H

47.

CH(CH 3 ) 2

CH 3

CH 3

CH 3

H

48.

H

CH(CH 3 ) 2

H

H

H

49.

CH 3

CH(CH 3 ) 2

H

CH 3

H

50.

H

CH(CH 3 ) 2

CH 3

H

H

51.

H

CH(CH 3 ) 2

H

CH 3

H

52.

CH 3

CH(CH 3 ) 2

CH 3

H

H

53.

CH 3

CH(CH 3 ) 2

H

CH 3

H

54.

H

CH(CH 3 ) 2

CH 3

CH 3

H

55.

CH 3

CH(CH 3 ) 2

CH 3

CH 3

H

56.

H

H

CH(CH 3 ) 2

H

H

57.

CH 3

H

CH(CH 3 ) 2

H

H

58.

H

CH 3

CH(CH 3 ) 2

H

H

59.

H

H

CH(CH 3 ) 2

CH 3

H

60.

CH 3

CH 3

CH(CH 3 ) 2

H

H

61.

CH 3

H

CH(CH 3 ) 2

CH 3

H

62.

H

CH 3

CH(CH 3 ) 2

CH 3

H

63.

CH 3

CH 3

CH(CH 3 ) 2

CH 3

H

64.

CH 2 CH(CH 3 ) 2

H

H

H

H

65.

CH 2 CH(CH 3 ) 2

CH 3

H

CH 3

H

66.

CH 2 CH(CH 3 ) 2

H

CH 3

H

H

67.

CH 2 CH(CH 3 ) 2

H

H

CH 3

H

68.

CH 2 CH(CH 3 ) 2

CH 3

CH 3

H

H

69.

CH 2 CH(CH 3 ) 2

CH 3

H

CH 3

H

70.

CH 2 CH(CH 3 ) 2

H

CH 3

CH 3

H

71.

CH 2 CH(CH 3 ) 2

CH 3

CH 3

CH 3

H

72.

H

CH 2 CH(CH 3 ) 2

H

H

H

73.

CH 3

CH 2 CH(CH 3 ) 2

H

CH 3

H

74.

H

CH 2 CH(CH 3 ) 2

CH 3

H

H

75.

H

CH 2 CH(CH 3 ) 2

H

CH 3

H

76.

CH 3

CH 2 CH(CH 3 ) 2

CH 3

H

H

77.

CH 3

CH 2 CH(CH 3 ) 2

H

CH 3

H

78.

H

CH 2 CH(CH 3 ) 2

CH 3

CH 3

H

79.

CH 3

CH 2 CH(CH 3 ) 2

CH 3

CH 3

H

80.

H

H

CH 2 CH(CH 3 ) 2

H

H

81.

CH 3

H

CH 2 CH(CH 3 ) 2

H

H

82.

H

CH 3

CH 2 CH(CH 3 ) 2

H

H

83.

H

H

CH 2 CH(CH 3 ) 2

CH 3

H

84.

CH 3

CH 3

CH 2 CH(CH 3 ) 2

H

H

85.

CH 3

H

CH 2 CH(CH 3 ) 2

CH 3

H

86.

H

CH 3

CH 2 CH(CH 3 ) 2

CH 3

H

87.

CH 3

CH 3

CH 2 CH(CH 3 ) 2

CH 3

H

88.

C(CH 3 ) 3

H

H

H

H

89.

C(CH 3 ) 3

CH 3

H

CH 3

H

90.

C(CH 3 ) 3

H

CH 3

H

H

91.

C(CH 3 ) 3

H

H

CH 3

H

92.

C(CH 3 ) 3

CH 3

CH 3

H

H

93.

C(CH 3 ) 3

CH 3

H

CH 3

H

94.

C(CH 3 ) 3

H

CH 3

CH 3

H

95.

C(CH 3 ) 3

CH 3

CH 3

CH 3

H

96.

H

C(CH 3 ) 3

H

H

H

97.

CH 3

C(CH 3 ) 3

H

CH 3

H

98.

H

C(CH 3 ) 3

CH 3

H

H

99.

H

C(CH 3 ) 3

H

CH 3

H

100.

CH 3

C(CH 3 ) 3

CH 3

H

H

101.

CH 3

C(CH 3 ) 3

H

CH 3

H

102.

H

C(CH 3 ) 3

CH 3

CH 3

H

103.

CH 3

C(CH 3 ) 3

CH 3

CH 3

H

104.

H

H

C(CH 3 ) 3

H

H

105.

CH 3

H

C(CH 3 ) 3

H

H

106.

H

CH 3

C(CH 3 ) 3

H

H

107.

H

H

C(CH 3 ) 3

CH 3

H

108.

CH 3

CH 3

C(CH 3 ) 3

H

H

109.

CH 3

H

C(CH 3 ) 3

CH 3

H

110.

H

CH 3

C(CH 3 ) 3

CH 3

H

111.

CH 3

CH 3

C(CH 3 ) 3

CH 3

H

112.

CH 2 C(CH 3 ) 3

H

H

H

H

113.

CH 2 C(CH 3 ) 3

CH 3

H

CH 3

H

114.

CH 2 C(CH 3 ) 3

H

CH 3

H

H

115.

CH 2 C(CH 3 ) 3

H

H

CH 3

H

116.

CH 2 C(CH 3 ) 3

CH 3

CH 3

H

H

117.

CH 2 C(CH 3 ) 3

CH 3

H

CH 3

H

118.

CH 2 C(CH 3 ) 3

H

CH 3

CH 3

H

119.

CH 2 C(CH 3 ) 3

CH 3

CH 3

CH 3

H

120.

H

CH 2 C(CH 3 ) 3

H

H

H

121.

CH 3

CH 2 C(CH 3 ) 3

H

CH 3

H

122.

H

CH 2 C(CH 3 ) 3

CH 3

H

H

123.

H

CH 2 C(CH 3 ) 3

H

CH 3

H

124.

CH 3

CH 2 C(CH 3 ) 3

CH 3

H

H

125.

CH 3

CH 2 C(CH 3 ) 3

H

CH 3

H

126.

H

CH 2 C(CH 3 ) 3

CH 3

CH 3

H

127.

CH 3

CH 2 C(CH 3 ) 3

CH 3

CH 3

H

128.

H

H

CH 2 C(CH 3 ) 3

H

H

129.

CH 3

H

CH 2 C(CH 3 ) 3

H

H

130.

H

CH 3

CH 2 C(CH 3 ) 3

H

H

131.

H

H

CH 2 C(CH 3 ) 3

CH 3

H

132.

CH 3

CH 3

CH 2 C(CH 3 ) 3

H

H

133.

CH 3

H

CH 2 C(CH 3 ) 3

CH 3

H

134.

H

CH 3

CH 2 C(CH 3 ) 3

CH 3

H

135.

CH 3

CH 3

CH 2 C(CH 3 ) 3

CH 3

H

136.

H

H

H

H

137.

CH 3

H

CH 3

H

138.

H

CH 3

H

H

139.

H

H

CH 3

H

140.

CH 3

CH 3

H

H

141.

CH 3

H

CH 3

H

142.

H

CH 3

CH 3

H

143.

CH 3

CH 3

CH 3

H

144.

H

H

H

H

145.

CH 3

H

CH 3

H

146.

H

CH 3

H

H

147.

H

H

CH 3

H

148.

CH 3

CH 3

H

H

149.

CH 3

H

CH 3

H

150.

H

CH 3

CH 3

H

151.

CH 3

CH 3

CH 3

H

152.

H

H

H

H

153.

CH 3

H

H

H

154.

H

CH 3

H

H

155.

H

H

CH 3

H

156.

CH 3

CH 3

H

H

157.

CH 3

H

CH 3

H

158.

H

CH 3

CH 3

H

159.

CH 3

CH 3

CH 3

H

160.

H

H

H

H

161.

CH 3

H

CH 3

H

162.

H

CH 3

H

H

163.

H

H

CH 3

H

164.

CH 3

CH 3

H

H

165.

CH 3

H

CH 3

H

166.

H

CH 3

CH 3

H

167.

CH 3

CH 3

CH 3

H

168.

H

H

H

H

169.

CH 3

H

CH 3

H

170.

H

CH 3

H

H

171.

H

H

CH 3

H

172.

CH 3

CH 3

H

H

173.

CH 3

H

CH 3

H

174.

H

CH 3

CH 3

H

175.

CH 3

CH 3

CH 3

H

176.

H

H

H

H

177.

CH 3

H

H

H

178.

H

CH 3

H

H

179.

H

H

CH 3

H

180.

CH 3

CH 3

H

H

181.

CH 3

H

CH 3

H

182.

H

CH 3

CH 3

H

183.

CH 3

CH 3

CH 3

H

184.

H

H

H

H

185.

CH 3

H

CH 3

H

186.

H

CH 3

H

H

187.

H

H

CH 3

H

188.

CH 3

CH 3

H

H

189.

CH 3

H

CH 3

H

190.

H

CH 3

CH 3

H

191.

CH 3

CH 3

CH 3

H

192.

H

H

H

H

193.

CH 3

H

CH 3

H

194.

H

CH 3

H

H

195.

H

H

CH 3

H

196.

CH 3

CH 3

H

H

197.

CH 3

H

CH 3

H

198.

H

CH 3

CH 3

H

199.

CH 3

CH 3

CH 3

H

200.

H

H

H

H

201.

CH 3

H

H

H

202.

H

CH 3

H

H

203.

H

H

CH 3

H

204.

CH 3

CH 3

H

H

205.

CH 3

H

CH 3

H

206.

H

CH 3

CH 3

H

207.

CH 3

CH 3

CH 3

H

208.

H

H

H

H

209.

CH 3

H

CH 3

H

210.

H

CH 3

H

H

211.

H

H

CH 3

H

212.

CH 3

CH 3

H

H

213.

CH 3

H

CH 3

H

214.

H

CH 3

CH 3

H

215.

CH 3

CH 3

CH 3

H

216.

H

H

H

H

217.

CH 3

H

CH 3

H

218.

H

CH 3

H

H

219.

H

H

CH 3

H

220.

CH 3

CH 3

H

H

221.

CH 3

H

CH 3

H

222.

H

CH 3

CH 3

H

223.

CH 3

CH 3

CH 3

H

224.

H

H

H

H

225.

CH 3

H

H

H

226.

H

CH 3

H

H

227.

H

H

CH 3

H

228.

CH 3

CH 3

H

H

229.

CH 3

H

CH 3

H

230.

H

CH 3

CH 3

H

231.

CH 3

CH 3

CH 3

H

232.

H

H

H

H

233.

CH 3

H

CH 3

H

234.

H

CH 3

H

H

235.

H

H

CH 3

H

236.

CH 3

CH 3

H

H

237.

CH 3

H

CH 3

H

238.

H

CH 3

CH 3

H

239.

CH 3

CH 3

CH 3

H

240.

H

H

H

H

241.

CH 3

H

CH 3

H

242.

H

CH 3

H

H

243.

H

H

CH 3

H

244.

CH 3

CH 3

H

H

245.

CH 3

H

CH 3

H

246.

H

CH 3

CH 3

H

247.

CH 3

CH 3

CH 3

H

248.

H

H

H

H

249.

CH 3

H

H

H

250.

H

CH 3

H

H

251.

H

H

CH 3

H

252.

CH 3

CH 3

H

H

253.

CH 3

H

CH 3

H

254.

H

CH 3

CH 3

H

255.

CH 3

CH 3

CH 3

H

256.

H

H

H

H

257.

CH 3

H

CH 3

H

258.

H

CH 3

H

H

259.

H

H

CH 3

H

260.

CH 3

CH 3

H

H

261.

CH 3

H

CH 3

H

262.

H

CH 3

CH 3

H

263.

CH 3

CH 3

CH 3

H

264.

H

H

H

H

265.

CH 3

H

CH 3

H

266.

H

CH 3

H

H

267.

H

H

CH 3

H

268.

CH 3

CH 3

H

H

269.

CH 3

H

CH 3

H

270.

H

CH 3

CH 3

H

271.

CH 3

CH 3

CH 3

H

272.

H

H

H

H

273.

CH 3

H

H

H

274.

H

CH 3

H

H

275.

H

H

CH 3

H

276.

CH 3

CH 3

H

H

277.

CH 3

H

CH 3

H

278.

H

CH 3

CH 3

H

279.

CH 3

CH 3

CH 3

H

280.

CH(CH 3 ) 2

H

CH 2 CH 3

H

H

281.

CH(CH 3 ) 2

H

CH(CH 3 ) 2

H

H

282.

CH(CH 3 ) 2

H

CH 2 CH(CH 3 ) 2

H

H

283.

CH(CH 3 ) 2

H

C(CH 3 ) 3

H

H

284.

CH(CH 3 ) 2

H

CH 2 C(CH 3 ) 3

H

H

285.

CH(CH 3 ) 2

H

H

H

286.

CH(CH 3 ) 2

H

H

H

287.

CH(CH 3 ) 2

H

H

H

288.

CH(CH 3 ) 2

H

H

H

289.

CH(CH 3 ) 2

H

H

H

290.

CH(CH 3 ) 2

H

H

H

291.

C(CH 3 ) 3

H

CH 2 CH 3

H

H

292.

C(CH 3 ) 3

H

CH(CH 3 ) 2

H

H

293.

C(CH 3 ) 3

H

CH 2 CH(CH 3 ) 2

H

H

294.

C(CH 3 ) 3

H

C(CH 3 ) 3

H

H

295.

C(CH 3 ) 3

H

CH 2 C(CH 3 ) 3

H

H

296.

C(CH 3 ) 3

H

H

H

297.

C(CH 3 ) 3

H

H

H

298.

C(CH 3 ) 3

H

H

H

299.

C(CH 3 ) 3

H

H

H

300.

C(CH 3 ) 3

H

H

H

301.

C(CH 3 ) 3

H

H

H

302.

CH 2 C(CH 3 ) 3

H

CH 2 CH 3

H

H

303.

CH 2 C(CH 3 ) 3

H

CH(CH 3 ) 2

H

H

304.

CH 2 C(CH 3 ) 3

H

CH 2 CH(CH 3 ) 2

H

H

305.

CH 2 C(CH 3 ) 3

H

C(CH 3 ) 3

H

H

306.

CH 2 C(CH 3 ) 3

H

CH 2 C(CH 3 ) 3

H

H

307.

CH 2 C(CH 3 ) 3

H

CH 2 CH 2 CF 3

H

H

308.

CH 2 C(CH 3 ) 3

H

CH 2 C(CH 3 ) 2 CF 3

H

H

309.

CH 2 C(CH 3 ) 3

H

H

H

310.

CH 2 C(CH 3 ) 3

H

H

H

311.

CH 2 C(CH 3 ) 3

H

H

H

312.

CH 2 C(CH 3 ) 3

H

H

H

313.

CH 2 C(CH 3 ) 3

H

H

H

314.

CH 2 C(CH 3 ) 3

H

H

H

315.

H

CH 2 CH 3

H

H

316.

H

CH(CH 3 ) 2

H

H

317.

H

CH 2 CH(CH 3 ) 2

H

H

318.

H

C(CH 3 ) 3

H

H

319.

H

CH 2 C(CH 3 ) 3

H

H

320.

H

H

H

321.

H

H

H

322.

H

H

H

323.

H

H

H

324.

H

H

H

325.

H

H

H

326.

H

CH 2 CH 3

H

H

327.

H

CH(CH 3 ) 2

H

H

328.

H

CH 2 CH(CH 3 ) 2

H

H

329.

H

C(CH 3 ) 3

H

H

330.

H

CH 2 C(CH 3 ) 3

H

H

331.

H

H

H

332.

H

H

H

333.

H

H

H

334.

H

H

H

335.

H

H

H

336.

H

H

H

337.

H

CH 2 CH(CH 3 ) 2

H

H

338.

H

C(CH 3 ) 3

H

H

339.

H

CH 2 C(CH 3 ) 3

H

H

340.

H

H

H

341.

H

H

H

342.

H

H

H

343.

H

H

H

344.

H

H

H

345.

H

H

H

346.

H

CH 2 CH(CH 3 ) 2

H

H

347.

H

C(CH 3 ) 3

H

H

348.

H

CH 2 C(CH 3 ) 3

H

H

349.

H

H

H

350.

H

H

H

351.

H

H

H

352.

H

H

H

353.

H

H

H

354.

H

H

H

355.

H

CH 2 CH(CH 3 ) 2

H

H

356.

H

C(CH 3 ) 3

H

H

357.

H

CH 2 C(CH 3 ) 3

H

H

358.

H

H

H

359.

H

H

H

360.

H

H

H

361.

H

H

H

362.

H

H

H

363.

H

H

H

364.

H

H

H

H

H

365.

CD 3

H

H

H

H

366.

H

CD 3

H

H

H

367.

H

H

CD 3

H

H

368.

CD 3

CD 3

H

CD 3

H

369.

CD 3

H

CD 3

H

H

370.

CD 3

H

H

CD 3

H

371.

H

CD 3

CD 3

H

H

372.

H

CD 3

H

CD 3

H

373.

H

H

CD 3

CD 3

H

374.

CD 3

CD 3

CD 3

H

H

375.

CD 3

CD 3

H

CD 3

H

376.

CD 3

H

CD 3

CD 3

H

377.

H

CD 3

CD 3

CD 3

H

378.

CD 3

CD 3

CD 3

CD 3

H

379.

CD 2 CH 3

H

H

H

H

380.

CD 2 CH 3

CD 3

H

CD 3

H

381.

CD 2 CH 3

H

CD 3

H

H

382.

CD 2 CH 3

H

H

CD 3

H

383.

CD 2 CH 3

CD 3

CD 3

H

H

384.

CD 2 CH 3

CD 3

H

CD 3

H

385.

CD 2 CH 3

H

CD 3

CD 3

H

386.

CD 2 CH 3

CD 3

CD 3

CD 3

H

387.

H

CD 2 CH 3

H

H

H

388.

CD 3

CD 2 CH 3

H

CD 3

H

389.

H

CD 2 CH 3

CD 3

H

H

390.

H

CD 2 CH 3

H

CD 3

H

391.

CD 3

CD 2 CH 3

CD 3

H

H

392.

CD 3

CD 2 CH 3

H

CD 3

H

393.

H

CD 2 CH 3

CD 3

CD 3

H

394.

CD 3

CD 2 CH 3

CD 3

CD 3

H

395.

H

H

CD 2 CH 3

H

H

396.

CD 3

H

CD 2 CH 3

H

H

397.

H

CD 3

CD 2 CH 3

H

H

398.

H

H

CD 2 CH 3

CD 3

H

399.

CD 3

CD 3

CD 2 CH 3

H

H

400.

CD 3

H

CD 2 CH 3

CD 3

H

401.

H

CD 3

CD 2 CH 3

CD 3

H

402.

CD 3

CD 3

CD 2 CH 3

CD 3

H

403.

CD(CH 3 ) 2

H

H

H

H

404.

CD(CH 3 ) 2

CD 3

H

CD 3

H

405.

CD(CH 3 ) 2

H

CD 3

H

H

406.

CD(CH 3 ) 2

H

H

CD 3

H

407.

CD(CH 3 ) 2

CD 3

CD 3

H

H

408.

CD(CH 3 ) 2

CD 3

H

CD 3

H

409.

CD(CH 3 ) 2

H

CD 3

CD 3

H

410.

CD(CH 3 ) 2

CD 3

CD 3

CD 3

H

411.

H

CD(CH 3 ) 2

H

H

H

412.

CD 3

CD(CH 3 ) 2

H

CD 3

H

413.

H

CD(CH 3 ) 2

CD 3

H

H

414.

H

CD(CH 3 ) 2

H

CD 3

H

415.

CD 3

CD(CH 3 ) 2

CD 3

H

H

416.

CD 3

CD(CH 3 ) 2

H

CD 3

H

417.

H

CD(CH 3 ) 2

CD 3

CD 3

H

418.

CD 3

CD(CH 3 ) 2

CD 3

CD 3

H

419.

H

H

CD(CH 3 ) 2

H

H

420.

CD 3

H

CD(CH 3 ) 2

H

H

421.

H

CD 3

CD(CH 3 ) 2

H

H

422.

H

H

CD(CH 3 ) 2

CD 3

H

423.

CD 3

CD 3

CD(CH 3 ) 2

H

H

424.

CD 3

H

CD(CH 3 ) 2

CD 3

H

425.

H

CD 3

CD(CH 3 ) 2

CD 3

H

426.

CD 3

CD 3

CD(CH 3 ) 2

CD 3

H

427.

CD(CD 3 ) 2

H

H

H

H

428.

CD(CD 3 ) 2

CD 3

H

CD 3

H

429.

CD(CD 3 ) 2

H

CD 3

H

H

430.

CD(CD 3 ) 2

H

H

CD 3

H

431.

CD(CD 3 ) 2

CD 3

CD 3

H

H

432.

CD(CD 3 ) 2

CD 3

H

CD 3

H

433.

CD(CD 3 ) 2

H

CD 3

CD 3

H

434.

CD(CD 3 ) 2

CD 3

CD 3

CD 3

H

435.

H

CD(CD 3 ) 2

H

H

H

436.

CH 3

CD(CD 3 ) 2

H

CD 3

H

437.

H

CD(CD 3 ) 2

CD 3

H

H

438.

H

CD(CD 3 ) 2

H

CD 3

H

439.

CD 3

CD(CD 3 ) 2

CD 3

H

H

440.

CD 3

CD(CD 3 ) 2

H

CD 3

H

441.

H

CD(CD 3 ) 2

CD 3

CD 3

H

442.

CD 3

CD(CD 3 ) 2

CD 3

CD 3

H

443.

H

H

CD(CD 3 ) 2

H

H

444.

CD 3

H

CD(CD 3 ) 2

H

H

445.

H

CD 3

CD(CD 3 ) 2

H

H

446.

H

H

CD(CD 3 ) 2

CD 3

H

447.

CD 3

CD 3

CD(CD 3 ) 2

H

H

448.

CD 3

H

CD(CD 3 ) 2

CD 3

H

449.

H

CD 3

CD(CD 3 ) 2

CD 3

H

450.

CD 3

CD 3

CD(CD 3 ) 2

CD 3

H

451.

CD 2 CH(CH 3 ) 2

H

H

H

H

452.

CD 2 CH(CH 3 ) 2

CD 3

H

CD 3

H

453.

CD 2 CH(CH 3 ) 2

H

CD 3

H

H

454.

CD 2 CH(CH 3 ) 2

H

H

CD 3

H

455.

CD 2 CH(CH 3 ) 2

CD 3

CD 3

H

H

456.

CD 2 CH(CH 3 ) 2

CD 3

H

CD 3

H

457.

CD 2 CH(CH 3 ) 2

H

CD 3

CD 3

H

458.

CD 2 CH(CH 3 ) 2

CD 3

CD 3

CD 3

H

459.

H

CD 2 CH(CH 3 ) 2

H

H

H

460.

CD 3

CD 2 CH(CH 3 ) 2

H

CD 3

H

461.

H

CD 2 CH(CH 3 ) 2

CD 3

H

H

462.

H

CD 2 CH(CH 3 ) 2

H

CD 3

H

463.

CD 3

CD 2 CH(CH 3 ) 2

CD 3

H

H

464.

CD 3

CD 2 CH(CH 3 ) 2

H

CD 3

H

465.

H

CD 2 CH(CH 3 ) 2

CD 3

CD 3

H

466.

CD 3

CD 2 CH(CH 3 ) 2

CD 3

CD 3

H

467.

H

H

CD 2 CH(CH 3 ) 2

H

H

468.

CD 3

H

CD 2 CH(CH 3 ) 2

H

H

469.

H

CD 3

CD 2 CH(CH 3 ) 2

H

H

470.

H

H

CD 2 CH(CH 3 ) 2

CD 3

H

471.

CD 3

CD 3

CD 2 CH(CH 3 ) 2

H

H

472.

CD 3

H

CD 2 CH(CH 3 ) 2

CD 3

H

473.

H

CD 3

CD 2 CH(CH 3 ) 2

CD 3

H

474.

CD 3

CD 3

CD 2 CH(CH 3 ) 2

CD 3

H

475.

CD 2 C(CH 3 ) 3

H

H

H

H

476.

CD 2 C(CH 3 ) 3

CD 3

H

CD 3

H

477.

CD 2 C(CH 3 ) 3

H

CD 3

H

H

478.

CD 2 C(CH 3 ) 3

H

H

CD 3

H

479.

CD 2 C(CH 3 ) 3

CD 3

CD 3

H

H

480.

CD 2 C(CH 3 ) 3

CD 3

H

CD 3

H

481.

CD 2 C(CH 3 ) 3

H

CD 3

CD 3

H

482.

CD 2 C(CH 3 ) 3

CD 3

CD 3

CD 3

H

483.

H

CD 2 C(CH 3 ) 3

H

H

H

484.

CD 3

CD 2 C(CH 3 ) 3

H

CD 3

H

485.

H

CD 2 C(CH 3 ) 3

CD 3

H

H

486.

H

CD 2 C(CH 3 ) 3

H

CD 3

H

487.

CD 3

CD 2 C(CH 3 ) 3

CD 3

H

H

488.

CD 3

CD 2 C(CH 3 ) 3

H

CD 3

H

489.

H

CD 2 C(CH 3 ) 3

CD 3

CD 3

H

490.

CD 3

CD 2 C(CH 3 ) 3

CD 3

CD 3

H

491.

H

H

CD 2 C(CH 3 ) 3

H

H

492.

CD 3

H

CD 2 C(CH 3 ) 3

H

H

493.

H

CD 3

CD 2 C(CH 3 ) 3

H

H

494.

H

H

CD 2 C(CH 3 ) 3

CD 3

H

495.

CD 3

CD 3

CD 2 C(CH 3 ) 3

H

H

496.

CD 3

H

CD 2 C(CH 3 ) 3

CD 3

H

497.

H

CD 3

CD 2 C(CH 3 ) 3

CD 3

H

498.

CD 3

CD 3

CD 2 C(CH 3 ) 3

CD 3

H

499.

H

H

H

H

500.

CD 3

H

CD 3

H

501.

H

CD 3

H

H

502.

H

H

CD 3

H

503.

CD 3

CD 3

H

H

504.

CD 3

H

CD 3

H

505.

H

CD 3

CD 3

H

506.

CD 3

CD 3

CD 3

H

507.

H

H

H

H

508.

CD 3

H

CD 3

H

509.

H

CD 3

H

H

510.

H

H

CD 3

H

511.

CD 3

CD 3

H

H

512.

CD 3

H

CD 3

H

513.

H

CD 3

CD 3

H

514.

CD 3

CD 3

CD 3

H

515.

H

H

H

H

516.

CD 3

H

H

H

517.

H

CD 3

H

H

518.

H

H

CD 3

H

519.

CD 3

CD 3

H

H

520.

CD 3

H

CD 3

H

521.

H

CD 3

CD 3

H

522.

CD 3

CD 3

CD 3

H

523.

H

H

H

H

524.

CD 3

H

CD 3

H

525.

H

CD 3

H

H

526.

H

H

CD 3

H

527.

CD 3

CD 3

H

H

528.

CD 3

H

CD 3

H

529.

H

CD 3

CD 3

H

530.

CD 3

CD 3

CD 3

H

531.

H

H

H

H

532.

CH 3

H

CD 3

H

533.

H

CD 3

H

H

534.

H

H

CD 3

H

535.

CD 3

CD 3

H

H

536.

CD 3

H

CD 3

H

537.

H

CD 3

CD 3

H

538.

CH 3

CD 3

CD 3

H

539.

H

H

H

H

540.

CD 3

H

H

H

541.

H

CD 3

H

H

542.

H

H

CD 3

H

543.

CD 3

CD 3

H

H

544.

CD 3

H

CD 3

H

545.

H

CD 3

CD 3

H

546.

CD 3

CD 3

CD 3

H

547.

H

H

H

H

548.

CD 3

H

CD 3

H

549.

H

CD 3

H

H

550.

H

H

CD 3

H

551.

CD 3

CD 3

H

H

552.

CD 3

H

CD 3

H

553.

H

CD 3

CD 3

H

554.

CD 3

CD 3

CD 3

H

555.

H

H

H

H

556.

CD 3

H

CD 3

H

557.

H

CD 3

H

H

558.

H

H

CD 3

H

559.

CD 3

CD 3

H

H

560.

CD 3

H

CD 3

H

561.

H

CD 3

CD 3

H

562.

CD 3

CD 3

CD 3

H

563.

H

H

H

H

564.

CD 3

H

H

H

565.

H

CD 3

H

H

566.

H

H

CD 3

H

567.

CD 3

CD 3

H

H

568.

CD 3

H

CD 3

H

569.

H

CD 3

CD 3

H

570.

CD 3

CD 3

CD 3

H

571.

H

H

H

H

572.

CD 3

H

CD 3

H

573.

H

CD 3

H

H

574.

H

H

CD 3

H

575.

CD 3

CD 3

H

H

576.

CD 3

H

CD 3

H

577.

H

CD 3

CD 3

H

578.

CD 3

CD 3

CD 3

H

579.

H

H

H

H

580.

CD 3

H

CD 3

H

581.

H

CD 3

H

H

582.

H

H

CD 3

H

583.

CD 3

CD 3

H

H

584.

CD 3

H

CD 3

H

585.

H

CD 3

CD 3

H

586.

CD 3

CD 3

CD 3

H

587.

H

H

H

H

588.

CD 3

H

H

H

589.

H

CD 3

H

H

590.

H

H

CD 3

H

591.

CD 3

CD 3

H

H

592.

CD 3

H

CD 3

H

593.

H

CD 3

CD 3

H

594.

CD 3

CD 3

CD 3

H

595.

H

H

H

H

596.

CD 3

H

CD 3

H

597.

H

CD 3

H

H

598.

H

H

CD 3

H

599.

CD 3

CD 3

H

H

600.

CD 3

H

CD 3

H

601.

H

CD 3

CD 3

H

602.

CD 3

CD 3

CD 3

H

603.

H

H

H

H

604.

CD 3

H

CD 3

H

605.

H

CD 3

H

H

606.

H

H

CD 3

H

607.

CD 3

CD 3

H

H

608.

CD 3

H

CD 3

H

609.

H

CD 3

CD 3

H

610.

CD 3

CD 3

CD 3

H

611.

H

H

H

H

612.

CD 3

H

H

H

613.

H

CD 3

H

H

614.

H

H

CD 3

H

615.

CD 3

CD 3

H

H

616.

CD 3

H

CD 3

H

617.

H

CD 3

CD 3

H

618.

CD 3

CD 3

CD 3

H

619.

H

H

H

H

620.

CD 3

H

CD 3

H

621.

H

CD 3

H

H

622.

H

H

CD 3

H

623.

CD 3

CD 3

H

H

624.

CD 3

H

CD 3

H

625.

H

CD 3

CD 3

H

626.

CD 3

CD 3

CD 3

H

627.

H

H

H

H

628.

CD 3

H

CD 3

H

629.

H

CD 3

H

H

630.

H

H

CD 3

H

631.

CD 3

CD 3

H

H

632.

CD 3

H

CD 3

H

633.

H

CD 3

CD 3

H

634.

CD 3

CD 3

CD 3

H

635.

H

H

H

H

636.

CD 3

H

H

H

637.

H

CD 3

H

H

638.

H

H

CD 3

H

639.

CD 3

CD 3

H

H

640.

CD 3

H

CD 3

H

641.

H

CD 3

CD 3

H

642.

CD 3

CD 3

CD 3

H

643.

CD(CH 3 ) 2

H

CD 2 CH 3

H

H

644.

CD(CH 3 ) 2

H

CD(CH 3 ) 2

H

H

645.

CD(CH 3 ) 2

H

CD 2 CH(CH 3 ) 2

H

H

646.

CD(CH 3 ) 2

H

C(CH 3 ) 3

H

H

647.

CD(CH 3 ) 2

H

CD 2 C(CH 3 ) 3

H

H

648.

CD(CH 3 ) 2

H

H

H

649.

CD(CH 3 ) 2

H

H

H

650.

CD(CH 3 ) 2

H

H

H

651.

CD(CH 3 ) 2

H

H

H

652.

CD(CH 3 ) 2

H

H

H

653.

CD(CH 3 ) 2

H

H

H

654.

C(CH 3 ) 3

H

CD 2 CH 3

H

H

655.

C(CH 3 ) 3

H

CD(CH 3 ) 2

H

H

656.

C(CH 3 ) 3

H

CD 2 CH(CH 3 ) 2

H

H

657.

C(CH 3 ) 3

H

C(CH 3 ) 3

H

H

658.

C(CH 3 ) 3

H

CD 2 C(CH 3 ) 3

H

H

659.

C(CH 3 ) 3

H

H

H

660.

C(CH 3 ) 3

H

H

H

661.

C(CH 3 ) 3

H

H

H

662.

C(CH 3 ) 3

H

H

H

663.

C(CH 3 ) 3

H

H

H

664.

C(CH 3 ) 3

H

H

H

665.

CD 2 C(CH 3 ) 3

H

CD 2 CH 3

H

H

666.

CD 2 C(CH 3 ) 3

H

CD(CH 3 ) 2

H

H

667.

CD 2 C(CH 3 ) 3

H

CD 2 CH(CH 3 ) 2

H

H

668.

CD 2 C(CH 3 ) 3

H

C(CH 3 ) 3

H

H

669.

CD 2 C(CH 3 ) 3

H

CD 2 C(CH 3 ) 3

H

H

670.

CD 2 C(CH 3 ) 3

H

H

H

671.

CD 2 C(CH 3 ) 3

H

H

H

672.

CD 2 C(CH 3 ) 3

H

H

H

673.

CD 2 C(CH 3 ) 3

H

H

H

674.

CD 2 C(CH 3 ) 3

H

H

H

675.

CD 2 C(CH 3 ) 3

H

H

H

676.

H

CD 2 CH 3

H

H

677.

H

CD(CH 3 ) 2

H

H

678.

H

CD 2 CH(CH 3 ) 2

H

H

679.

H

C(CH 3 ) 3

H

H

680.

H

CD 2 C(CH 3 ) 3

H

H

681.

H

H

H

682.

H

H

H

683.

H

H

H

684.

H

H

H

685.

H

H

H

686.

H

H

H

687.

H

CD 2 CH 3

H

H

688.

H

CD(CH 3 ) 2

H

H

689.

H

CD 2 CH(CH 3 ) 2

H

H

690.

H

C(CH 3 ) 3

H

H

691.

H

CD 2 C(CH 3 ) 3

H

H

692.

H

H

H

693.

H

H

H

694.

H

H

H

695.

H

H

H

696.

H

H

H

697.

H

H

H

698.

H

CD 2 CH 3

H

H

699.

H

CD(CH 3 ) 2

H

H

700.

H

CD 2 CH(CH 3 ) 2

H

H

701.

H

C(CH 3 ) 3

H

H

702.

H

CD 2 C(CH 3 ) 3

H

H

703.

H

H

H

704.

H

H

H

705.

H

H

H

706.

H

H

H

707.

H

H

H

708.

H

H

H

709.

H

CD 2 CH 3

H

H

710.

H

CD(CH 3 ) 2

H

H

711.

H

CD 2 CH(CH 3 ) 2

H

H

712.

H

C(CH 3 ) 3

H

H

713.

H

CD 2 C(CH 3 ) 3

H

H

714.

H

H

H

715.

H

H

H

716.

H

H

H

717.

H

H

H

718.

H

H

H

719.

H

H

H

720.

H

CD 2 CH 3

H

H

721.

H

CD(CH 3 ) 2

H

H

722.

H

CD 2 CH(CH 3 ) 2

H

H

723.

H

C(CH 3 ) 3

H

H

724.

H

CD 2 C(CH 3 ) 3

H

H

725.

H

H

H

726.

H

H

H

727.

H

H

H

728.

H

H

H

729.

H

H

H

730.

H

H

H

731.

H

H

H

H

Ph

732.

CH 3

H

H

H

Ph

733.

H

CH 3

H

H

Ph

734.

H

H

CH 3

H

Ph

735.

CH 3

CH 3

H

CH 3

Ph

736.

CH 3

H

CH 3

H

Ph

737.

CH 3

H

H

CH 3

Ph

738.

H

CH 3

CH 3

H

Ph

739.

H

CH 3

H

CH 3

Ph

740.

H

H

CH 3

CH 3

Ph

741.

CH 3

CH 3

CH 3

H

Ph

742.

CH 3

CH 3

H

CH 3

Ph

743.

CH 3

H

CH 3

CH 3

Ph

744.

H

CH 3

CH 3

CH 3

Ph

745.

CH 3

CH 3

CH 3

CH 3

Ph

746.

CH 2 CH 3

H

H

H

Ph

747.

CH 2 CH 3

CH 3

H

CH 3

Ph

748.

CH 2 CH 3

H

CH 3

H

Ph

749.

CH 2 CH 3

H

H

CH 3

Ph

750.

CH 2 CH 3

CH 3

CH 3

H

Ph

751.

CH 2 CH 3

CH 3

H

CH 3

Ph

752.

CH 2 CH 3

H

CH 3

CH 3

Ph

753.

CH 2 CH 3

CH 3

CH 3

CH 3

Ph

754.

H

CH 2 CH 3

H

H

Ph

755.

CH 3

CH 2 CH 3

H

CH 3

Ph

756.

H

CH 2 CH 3

CH 3

H

Ph

757.

H

CH 2 CH 3

H

CH 3

Ph

758.

CH 3

CH 2 CH 3

CH 3

H

Ph

759.

CH 3

CH 2 CH 3

H

CH 3

Ph

760.

H

CH 2 CH 3

CH 3

CH 3

Ph

761.

CH 3

CH 2 CH 3

CH 3

CH 3

Ph

762.

H

H

CH 2 CH 3

H

Ph

763.

CH 3

H

CH 2 CH 3

H

Ph

764.

H

CH 3

CH 2 CH 3

H

Ph

765.

H

H

CH 2 CH 3

CH 3

Ph

766.

CH 3

CH 3

CH 2 CH 3

H

Ph

767.

CH 3

H

CH 2 CH 3

CH 3

Ph

768.

H

CH 3

CH 2 CH 3

CH 3

Ph

769.

CH 3

CH 3

CH 2 CH 3

CH 3

Ph

770.

CH(CH 3 ) 2

H

H

H

Ph

771.

CH(CH 3 ) 2

CH 3

H

CH 3

Ph

772.

CH(CH 3 ) 2

H

CH 3

H

Ph

773.

CH(CH 3 ) 2

H

H

CH 3

Ph

774.

CH(CH 3 ) 2

CH 3

CH 3

H

Ph

775.

CH(CH 3 ) 2

CH 3

H

CH 3

Ph

776.

CH(CH 3 ) 2

H

CH 3

CH 3

Ph

777.

CH(CH 3 ) 2

CH 3

CH 3

CH 3

Ph

778.

H

CH(CH 3 ) 2

H

H

Ph

779.

CH 3

CH(CH 3 ) 2

H

CH 3

Ph

780.

H

CH(CH 3 ) 2

CH 3

H

Ph

781.

H

CH(CH 3 ) 2

H

CH 3

Ph

782.

CH 3

CH(CH 3 ) 2

CH 3

H

Ph

783.

CH 3

CH(CH 3 ) 2

H

CH 3

Ph

784.

H

CH(CH 3 ) 2

CH 3

CH 3

Ph

785.

CH 3

CH(CH 3 ) 2

CH 3

CH 3

Ph

786.

H

H

CH(CH 3 ) 2

H

Ph

787.

CH 3

H

CH(CH 3 ) 2

H

Ph

788.

H

CH 3

CH(CH 3 ) 2

H

Ph

789.

H

H

CH(CH 3 ) 2

CH 3

Ph

790.

CH 3

CH 3

CH(CH 3 ) 2

H

Ph

791.

CH 3

H

CH(CH 3 ) 2

CH 3

Ph

792.

H

CH 3

CH(CH 3 ) 2

CH 3

Ph

793.

CH 3

CH 3

CH(CH 3 ) 2

CH 3

Ph

794.

CH 2 CH(CH 3 ) 2

H

H

H

Ph

795.

CH 2 CH(CH 3 ) 2

CH 3

H

CH 3

Ph

796.

CH 2 CH(CH 3 ) 2

H

CH 3

H

Ph

797.

CH 2 CH(CH 3 ) 2

H

H

CH 3

Ph

798.

CH 2 CH(CH 3 ) 2

CH 3

CH 3

H

Ph

799.

CH 2 CH(CH 3 ) 2

CH 3

H

CH 3

Ph

800.

CH 2 CH(CH 3 ) 2

H

CH 3

CH 3

Ph

801.

CH 2 CH(CH 3 ) 2

CH 3

CH 3

CH 3

Ph

802.

H

CH 2 CH(CH 3 ) 2

H

H

Ph

803.

CH 3

CH 2 CH(CH 3 ) 2

H

CH 3

Ph

804.

H

CH 2 CH(CH 3 ) 2

CH 3

H

Ph

805.

H

CH 2 CH(CH 3 ) 2

H

CH 3

Ph

806.

CH 3

CH 2 CH(CH 3 ) 2

CH 3

H

Ph

807.

CH 3

CH 2 CH(CH 3 ) 2

H

CH 3

Ph

808.

H

CH 2 CH(CH 3 ) 2

CH 3

CH 3

Ph

809.

CH 3

CH 2 CH(CH 3 ) 2

CH 3

CH 3

Ph

810.

H

H

CH 2 CH(CH 3 ) 2

H

Ph

811.

CH 3

H

CH 2 CH(CH 3 ) 2

H

Ph

812.

H

CH 3

CH 2 CH(CH 3 ) 2

H

Ph

813.

H

H

CH 2 CH(CH 3 ) 2

CH 3

Ph

814.

CH 3

CH 3

CH 2 CH(CH 3 ) 2

H

Ph

815.

CH 3

H

CH 2 CH(CH 3 ) 2

CH 3

Ph

816.

H

CH 3

CH 2 CH(CH 3 ) 2

CH 3

Ph

817.

CH 3

CH 3

CH 2 CH(CH 3 ) 2

CH 3

Ph

818.

C(CH 3 ) 3

H

H

H

Ph

819.

C(CH 3 ) 3

CH 3

H

CH 3

Ph

820.

C(CH 3 ) 3

H

CH 3

H

Ph

821.

C(CH 3 ) 3

H

H

CH 3

Ph

822.

C(CH 3 ) 3

CH 3

CH 3

H

Ph

823.

C(CH 3 ) 3

CH 3

H

CH 3

Ph

824.

C(CH 3 ) 3

H

CH 3

CH 3

Ph

825.

C(CH 3 ) 3

CH 3

CH 3

CH 3

Ph

826.

H

C(CH 3 ) 3

H

H

Ph

827.

CH 3

C(CH 3 ) 3

H

CH 3

Ph

828.

H

C(CH 3 ) 3

CH 3

H

Ph

829.

H

C(CH 3 ) 3

H

CH 3

Ph

830.

CH 3

C(CH 3 ) 3

CH 3

H

Ph

831.

CH 3

C(CH 3 ) 3

H

CH 3

Ph

832.

H

C(CH 3 ) 3

CH 3

CH 3

Ph

833.

CH 3

C(CH 3 ) 3

CH 3

CH 3

Ph

834.

H

H

C(CH 3 ) 3

H

Ph

835.

CH 3

H

C(CH 3 ) 3

H

Ph

836.

H

CH 3

C(CH 3 ) 3

H

Ph

837.

H

H

C(CH 3 ) 3

CH 3

Ph

838.

CH 3

CH 3

C(CH 3 ) 3

H

Ph

839.

CH 3

H

C(CH 3 ) 3

CH 3

Ph

840.

H

CH 3

C(CH 3 ) 3

CH 3

Ph

841.

CH 3

CH 3

C(CH 3 ) 3

CH 3

Ph

842.

CH 2 C(CH 3 ) 3

H

H

H

Ph

843.

CH 2 C(CH 3 ) 3

CH 3

H

CH 3

Ph

844.

CH 2 C(CH 3 ) 3

H

CH 3

H

Ph

845.

CH 2 C(CH 3 ) 3

H

H

CH 3

Ph

846.

CH 2 C(CH 3 ) 3

CH 3

CH 3

H

Ph

847.

CH 2 C(CH 3 ) 3

CH 3

H

CH 3

Ph

848.

CH 2 C(CH 3 ) 3

H

CH 3

CH 3

Ph

849.

CH 2 C(CH 3 ) 3

CH 3

CH 3

CH 3

Ph

850.

H

CH 2 C(CH 3 ) 3

H

H

Ph

851.

CH 3

CH 2 C(CH 3 ) 3

H

CH 3

Ph

852.

H

CH 2 C(CH 3 ) 3

CH 3

H

Ph

853.

H

CH 2 C(CH 3 ) 3

H

CH 3

Ph

854.

CH 3

CH 2 C(CH 3 ) 3

CH 3

H

Ph

855.

CH 3

CH 2 C(CH 3 ) 3

H

CH 3

Ph

856.

H

CH 2 C(CH 3 ) 3

CH 3

CH 3

Ph

857.

CH 3

CH 2 C(CH 3 ) 3

CH 3

CH 3

Ph

858.

H

H

CH 2 C(CH 3 ) 3

H

Ph

859.

CH 3

H

CH 2 C(CH 3 ) 3

H

Ph

860.

H

CH 3

CH 2 C(CH 3 ) 3

H

Ph

861.

H

H

CH 2 C(CH 3 ) 3

CH 3

Ph

862.

CH 3

CH 3

CH 2 C(CH 3 ) 3

H

Ph

863.

CH 3

H

CH 2 C(CH 3 ) 3

CH 3

Ph

864.

H

CH 3

CH 2 C(CH 3 ) 3

CH 3

Ph

865.

CH 3

CH 3

CH 2 C(CH 3 ) 3

CH 3

Ph

866.

H

H

H

Ph

867.

CH 3

H

CH 3

Ph

868.

H

CH 3

H

Ph

869.

H

H

CH 3

Ph

870.

CH 3

CH 3

H

Ph

871.

CH 3

H

CH 3

Ph

872.

H

CH 3

CH 3

Ph

873.

CH 3

CH 3

CH 3

Ph

874.

H

H

H

Ph

875.

CH 3

H

CH 3

Ph

876.

H

CH 3

H

Ph

877.

H

H

CH 3

Ph

878.

CH 3

CH 3

H

Ph

879.

CH 3

H

CH 3

Ph

880.

H

CH 3

CH 3

Ph

881.

CH 3

CH 3

CH 3

Ph

882.

H

H

H

Ph

883.

CH 3

H

H

Ph

884.

H

CH 3

H

Ph

885.

H

H

CH 3

Ph

886.

CH 3

CH 3

H

Ph

887.

CH 3

H

CH 3

Ph

888.

H

CH 3

CH 3

Ph

889.

CH 3

CH 3

CH 3

Ph

890.

H

H

H

Ph

891.

CH 3

H

CH 3

Ph

892.

H

CH 3

H

Ph

893.

H

H

CH 3

Ph

894.

CH 3

CH 3

H

Ph

895.

CH 3

H

CH 3

Ph

896.

H

CH 3

CH 3

Ph

897.

CH 3

CH 3

CH 3

Ph

898.

H

H

H

Ph

899.

CH 3

H

CH 3

Ph

900.

H

CH 3

H

Ph

901.

H

H

CH 3

Ph

902.

CH 3

CH 3

H

Ph

903.

CH 3

H

CH 3

Ph

904.

H

CH 3

CH 3

Ph

905.

CH 3

CH 3

CH 3

Ph

906.

H

H

H

Ph

907.

CH 3

H

H

Ph

908.

H

CH 3

H

Ph

909.

H

H

CH 3

Ph

910.

CH 3

CH 3

H

Ph

911.

CH 3

H

CH 3

Ph

912.

H

CH 3

CH 3

Ph

913.

CH 3

CH 3

CH 3

Ph

914.

H

H

H

Ph

915.

CH 3

H

CH 3

Ph

916.

H

CH 3

H

Ph

917.

H

H

CH 3

Ph

918.

CH 3

CH 3

H

Ph

919.

CH 3

H

CH 3

Ph

920.

H

CH 3

CH 3

Ph

921.

CH 3

CH 3

CH 3

Ph

922.

H

H

H

Ph

923.

CH 3

H

CH 3

Ph

924.

H

CH 3

H

Ph

925.

H

H

CH 3

Ph

926.

CH 3

CH 3

H

Ph

927.

CH 3

H

CH 3

Ph

928.

H

CH 3

CH 3

Ph

929.

CH 3

CH 3

CH 3

Ph

930.

H

H

H

Ph

931.

CH 3

H

H

Ph

932.

H

CH 3

H

Ph

933.

H

H

CH 3

Ph

934.

CH 3

CH 3

H

Ph

935.

CH 3

H

CH 3

Ph

936.

H

CH 3

CH 3

Ph

937.

CH 3

CH 3

CH 3

Ph

938.

H

H

H

Ph

939.

CH 3

H

CH 3

Ph

940.

H

CH 3

H

Ph

941.

H

H

CH 3

Ph

942.

CH 3

CH 3

H

Ph

943.

CH 3

H

CH 3

Ph

944.

H

CH 3

CH 3

Ph

945.

CH 3

CH 3

CH 3

Ph

946.

H

H

H

Ph

947.

CH 3

H

CH 3

Ph

948.

H

CH 3

H

Ph

949.

H

H

CH 3

Ph

950.

CH 3

CH 3

H

Ph

951.

CH 3

H

CH 3

Ph

952.

H

CH 3

CH 3

Ph

953.

CH 3

CH 3

CH 3

Ph

954.

H

H

H

Ph

955.

CH 3

H

H

Ph

956.

H

CH 3

H

Ph

957.

H

H

CH 3

Ph

958.

CH 3

CH 3

H

Ph

959.

CH 3

H

CH 3

Ph

960.

H

CH 3

CH 3

Ph

961.

CH 3

CH 3

CH 3

Ph

962.

H

H

H

Ph

963.

CH 3

H

CH 3

Ph

964.

H

CH 3

H

Ph

965.

H

H

CH 3

Ph

966.

CH 3

CH 3

H

Ph

967.

CH 3

H

CH 3

Ph

968.

H

CH 3

CH 3

Ph

969.

CH 3

CH 3

CH 3

Ph

970.

H

H

H

Ph

971.

CH 3

H

CH 3

Ph

972.

H

CH 3

H

Ph

973.

H

H

CH 3

Ph

974.

CH 3

CH 3

H

Ph

975.

CH 3

H

CH 3

Ph

976.

H

CH 3

CH 3

Ph

977.

CH 3

CH 3

CH 3

Ph

978.

H

H

H

Ph

979.

CH 3

H

H

Ph

980.

H

CH 3

H

Ph

981.

H

H

CH 3

Ph

982.

CH 3

CH 3

H

Ph

983.

CH 3

H

CH 3

Ph

984.

H

CH 3

CH 3

Ph

985.

CH 3

CH 3

CH 3

Ph

986.

H

H

H

Ph

987.

CH 3

H

CH 3

Ph

988.

H

CH 3

H

Ph

989.

H

H

CH 3

Ph

990.

CH 3

CH 3

H

Ph

991.

CH 3

H

CH 3

Ph

992.

H

CH 3

CH 3

Ph

993.

CH 3

CH 3

CH 3

Ph

994.

H

H

H

Ph

995.

CH 3

H

CH 3

Ph

996.

H

CH 3

H

Ph

997.

H

H

CH 3

Ph

998.

CH 3

CH 3

H

Ph

999.

CH 3

H

CH 3

Ph

1000.

H

CH 3

CH 3

Ph

1001.

CH 3

CH 3

CH 3

Ph

1002.

H

H

H

Ph

1003.

CH 3

H

H

Ph

1004.

H

CH 3

H

Ph

1005.

H

H

CH 3

Ph

1006.

CH 3

CH 3

H

Ph

1007.

CH 3

H

CH 3

Ph

1008.

H

CH 3

CH 3

Ph

1009.

CH 3

CH 3

CH 3

Ph

1010.

CH(CH 3 ) 2

H

CH 2 CH 3

H

Ph

1011.

CH(CH 3 ) 2

H

CH(CH 3 ) 2

H

Ph

1012.

CH(CH 3 ) 2

H

CH 2 CH(CH 3 ) 2

H

Ph

1013.

CH(CH 3 ) 2

H

C(CH 3 ) 3

H

Ph

1014.

CH(CH 3 ) 2

H

CH 2 C(CH 3 ) 3

H

Ph

1015.

CH(CH 3 ) 2

H

H

Ph

1016.

CH(CH 3 ) 2

H

H

Ph

1017.

CH(CH 3 ) 2

H

H

Ph

1018.

CH(CH 3 ) 2

H

H

Ph

1019.

CH(CH 3 ) 2

H

H

Ph

1020.

CH(CH 3 ) 2

H

H

Ph

1021.

C(CH 3 ) 3

H

CH 2 CH 3

H

Ph

1022.

C(CH 3 ) 3

H

CH(CH 3 ) 2

H

Ph

1023.

C(CH 3 ) 3

H

CH 2 CH(CH 3 ) 2

H

Ph

1024.

C(CH 3 ) 3

H

C(CH 3 ) 3

H

Ph

1025.

C(CH 3 ) 3

H

CH 2 C(CH 3 ) 3

H

Ph

1026.

C(CH 3 ) 3

H

H

Ph

1027.

C(CH 3 ) 3

H

H

Ph

1028.

C(CH 3 ) 3

H

H

Ph

1029.

C(CH 3 ) 3

H

H

Ph

1030.

C(CH 3 ) 3

H

H

Ph

1031.

C(CH 3 ) 3

H

H

Ph

1032.

CH 2 C(CH 3 ) 3

H

CH 2 CH 3

H

Ph

1033.

CH 2 C(CH 3 ) 3

H

CH(CH 3 ) 2

H

Ph

1034.

CH 2 C(CH 3 ) 3

H

CH 2 CH(CH 3 ) 2

H

Ph

1035.

CH 2 C(CH 3 ) 3

H

C(CH 3 ) 3

H

Ph

1036.

CH 2 C(CH 3 ) 3

H

CH 2 C(CH 3 ) 3

H

Ph

1037.

CH 2 C(CH 3 ) 3

H

H

Ph

1038.

CH 2 C(CH 3 ) 3

H

H

Ph

1039.

CH 2 C(CH 3 ) 3

H

H

Ph

1040.

CH 2 C(CH 3 ) 3

H

H

Ph

1041.

CH 2 C(CH 3 ) 3

H

H

Ph

1042.

CH 2 C(CH 3 ) 3

H

H

Ph

1043.

H

CH 2 CH 3

H

Ph

1044.

H

CH(CH 3 ) 2

H

Ph

1045.

H

CH 2 CH(CH 3 ) 2

H

Ph

1046.

H

C(CH 3 ) 3

H

Ph

1047.

H

CH 2 C(CH 3 ) 3

H

Ph

1048.

H

H

Ph

1049.

H

H

Ph

1050.

H

H

Ph

1051.

H

H

Ph

1052.

H

H

Ph

1053.

H

H

Ph

1054.

H

CH 2 CH 3

H

Ph

1055.

H

CH(CH 3 ) 2

H

Ph

1056.

H

CH 2 CH(CH 3 ) 2

H

Ph

1057.

H

C(CH 3 ) 3

H

Ph

1058.

H

CH 2 C(CH 3 ) 3

H

Ph

1059.

H

H

Ph

1060.

H

H

Ph

1061.

H

H

Ph

1062.

H

H

Ph

1063.

H

H

Ph

1064.

H

H

Ph

1065.

H

CH 2 CH(CH 3 ) 2

H

Ph

1066.

H

C(CH 3 ) 3

H

Ph

1067.

H

CH 2 C(CH 3 ) 3

H

Ph

1068.

H

H

Ph

1069.

H

H

Ph

1070.

H

H

Ph

1071.

H

H

Ph

1072.

H

H

Ph

1073.

H

H

Ph

1074.

H

CH 2 CH(CH 3 ) 2

H

Ph

1075.

H

C(CH 3 ) 3

H

Ph

1076.

H

CH 2 C(CH 3 ) 3

H

Ph

1077.

H

H

Ph

1078.

H

H

Ph

1079.

H

H

Ph

1080.

H

H

Ph

1081.

H

H

Ph

1082.

H

H

Ph

1083.

H

CH 2 CH(CH 3 ) 2

H

Ph

1084.

H

C(CH 3 ) 3

H

Ph

1085.

H

CH 2 C(CH 3 ) 3

H

Ph

1086.

H

H

Ph

1087.

H

H

Ph

1088.

H

H

Ph

1089.

H

H

Ph

1090.

H

H

Ph

1091.

H

H

Ph

1092.

H

H

H

H

Ph

1093.

CD 3

H

H

H

Ph

1094.

H

CD 3

H

H

Ph

1095.

H

H

CD 3

H

Ph

1096.

CD 3

CD 3

H

CD 3

Ph

1097.

CD 3

H

CD 3

H

Ph

1098.

CD 3

H

H

CD 3

Ph

1099.

H

CD 3

CD 3

H

Ph

1100.

H

CD 3

H

CD 3

Ph

1101.

H

H

CD 3

CD 3

Ph

1102.

CD 3

CD 3

CD 3

H

Ph

1103.

CD 3

CD 3

H

CD 3

Ph

1104.

CD 3

H

CD 3

CD 3

Ph

1105.

H

CD 3

CD 3

CD 3

Ph

1106.

CD 3

CD 3

CD 3

CD 3

Ph

1107.

CD 2 CH 3

H

H

H

Ph

1108.

CD 2 CH 3

CD 3

H

CD 3

Ph

1109.

CD 2 CH 3

H

CD 3

H

Ph

1110.

CD 2 CH 3

H

H

CD 3

Ph

1111.

CD 2 CH 3

CD 3

CD 3

H

Ph

1112.

CD 2 CH 3

CD 3

H

CD 3

Ph

1113.

CD 2 CH 3

H

CD 3

CD 3

Ph

1114.

CD 2 CH 3

CD 3

CD 3

CD 3

Ph

1115.

H

CD 2 CH 3

H

H

Ph

1116.

CH 3

CD 2 CH 3

H

CD 3

Ph

1117.

H

CD 2 CH 3

CD 3

H

Ph

1118.

H

CD 2 CH 3

H

CD 3

Ph

1119.

CD 3

CD 2 CH 3

CD 3

H

Ph

1120.

CD 3

CD 2 CH 3

H

CD 3

Ph

1121.

H

CD 2 CH 3

CD 3

CD 3

Ph

1122.

CD 3

CD 2 CH 3

CD 3

CD 3

Ph

1123.

H

H

CD 2 CH 3

H

Ph

1124.

CD 3

H

CD 2 CH 3

H

Ph

1125.

H

CD 3

CD 2 CH 3

H

Ph

1126.

H

H

CD 2 CH 3

CD 3

Ph

1127.

CD 3

CD 3

CD 2 CH 3

H

Ph

1128.

CD 3

H

CD 2 CH 3

CD 3

Ph

1129.

H

CD 3

CD 2 CH 3

CD 3

Ph

1130.

CD 3

CD 3

CD 2 CH 3

CD 3

Ph

1131.

CD(CH 3 ) 2

H

H

H

Ph

1132.

CD(CH 3 ) 2

CD 3

H

CD 3

Ph

1133.

CD(CH 3 ) 2

H

CD 3

H

Ph

1134.

CD(CH 3 ) 2

H

H

CD 3

Ph

1135.

CD(CH 3 ) 2

CD 3

CD 3

H

Ph

1136.

CD(CH 3 ) 2

CD 3

H

CD 3

Ph

1137.

CD(CH 3 ) 2

H

CD 3

CD 3

Ph

1138.

CD(CH 3 ) 2

CD 3

CD 3

CD 3

Ph

1139.

H

CD(CH 3 ) 2

H

H

Ph

1140.

CD 3

CD(CH 3 ) 2

H

CD 3

Ph

1141.

H

CD(CH 3 ) 2

CD 3

H

Ph

1142.

H

CD(CH 3 ) 2

H

CD 3

Ph

1143.

CD 3

CD(CH 3 ) 2

CD 3

H

Ph

1144.

CD 3

CD(CH 3 ) 2

H

CD 3

Ph

1145.

H

CD(CH 3 ) 2

CD 3

CD 3

Ph

1146.

CD 3

CD(CH 3 ) 2

CD 3

CD 3

Ph

1147.

H

H

CD(CH 3 ) 2

H

Ph

1148.

CD 3

H

CD(CH 3 ) 2

H

Ph

1149.

H

CD 3

CD(CH 3 ) 2

H

Ph

1150.

H

H

CD(CH 3 ) 2

CD 3

Ph

1151.

CD 3

CD 3

CD(CH 3 ) 2

H

Ph

1152.

CD 3

H

CD(CH 3 ) 2

CD 3

Ph

1153.

H

CD 3

CD(CH 3 ) 2

CD 3

Ph

1154.

CD 3

CD 3

CD(CH 3 ) 2

CD 3

Ph

1155.

CD(CD 3 ) 2

H

H

H

Ph

1156.

CD(CD 3 ) 2

CD 3

H

CD 3

Ph

1157.

CD(CD 3 ) 2

H

CD 3

H

Ph

1158.

CD(CD 3 ) 2

H

H

CD 3

Ph

1159.

CD(CD 3 ) 2

CD 3

CD 3

H

Ph

1160.

CD(CD 3 ) 2

CD 3

H

CD 3

Ph

1161.

CD(CD 3 ) 2

H

CD 3

CD 3

Ph

1162.

CD(CD 3 ) 2

CD 3

CD 3

CD 3

Ph

1163.

H

CD(CD 3 ) 2

H

H

Ph

1164.

CH 3

CD(CD 3 ) 2

H

CD 3

Ph

1165.

H

CD(CD 3 ) 2

CD 3

H

Ph

1166.

H

CD(CD 3 ) 2

H

CD 3

Ph

1167.

CD 3

CD(CD 3 ) 2

CD 3

H

Ph

1168.

CD 3

CD(CD 3 ) 2

H

CD 3

Ph

1169.

H

CD(CD 3 ) 2

CD 3

CD 3

Ph

1170.

CD 3

CD(CD 3 ) 2

CD 3

CD 3

Ph

1171.

H

H

CD(CD 3 ) 2

H

Ph

1172.

CD 3

H

CD(CD 3 ) 2

H

Ph

1173.

H

CD 3

CD(CD 3 ) 2

H

Ph

1174.

H

H

CD(CD 3 ) 2

CD 3

Ph

1175.

CD 3

CD 3

CD(CD 3 ) 2

H

Ph

1176.

CD 3

H

CD(CD 3 ) 2

CD 3

Ph

1177.

H

CD 3

CD(CD 3 ) 2

CD 3

Ph

1178.

CD 3

CD 3

CD(CD 3 ) 2

CD 3

Ph

1179.

CD 2 CH(CH 3 ) 2

H

H

H

Ph

1180.

CD 2 CH(CH 3 ) 2

CD 3

H

CD 3

Ph

1181.

CD 2 CH(CH 3 ) 2

H

CD 3

H

Ph

1182.

CD 2 CH(CH 3 ) 2

H

H

CD 3

Ph

1183.

CD 2 CH(CH 3 ) 2

CD 3

CD 3

H

Ph

1184.

CD 2 CH(CH 3 ) 2

CD 3

H

CD 3

Ph

1185.

CD 2 CH(CH 3 ) 2

H

CD 3

CD 3

Ph

1186.

CD 2 CH(CH 3 ) 2

CD 3

CD 3

CD 3

Ph

1187.

H

CD 2 CH(CH 3 ) 2

H

H

Ph

1188.

CD 3

CD 2 CH(CH 3 ) 2

H

CD 3

Ph

1189.

H

CD 2 CH(CH 3 ) 2

CD 3

H

Ph

1190.

H

CD 2 CH(CH 3 ) 2

H

CD 3

Ph

1191.

CD 3

CD 2 CH(CH 3 ) 2

CD 3

H

Ph

1192.

CD 3

CD 2 CH(CH 3 ) 2

H

CD 3

Ph

1193.

H

CD 2 CH(CH 3 ) 2

CD 3

CD 3

Ph

1194.

CD 3

CD 2 CH(CH 3 ) 2

CD 3

CD 3

Ph

1195.

H

H

CD 2 CH(CH 3 ) 2

H

Ph

1196.

CD 3

H

CD 2 CH(CH 3 ) 2

H

Ph

1197.

H

CD 3

CD 2 CH(CH 3 ) 2

H

Ph

1198.

H

H

CD 2 CH(CH 3 ) 2

CD 3

Ph

1199.

CD 3

CD 3

CD 2 CH(CH 3 ) 2

H

Ph

1200.

CD 3

H

CD 2 CH(CH 3 ) 2

CD 3

Ph

1201.

H

CD 3

CD 2 CH(CH 3 ) 2

CD 3

Ph

1202.

CD 3

CD 3

CD 2 CH(CH 3 ) 2

CD 3

Ph

1203.

CD 2 C(CH 3 ) 3

H

H

H

Ph

1204.

CD 2 C(CH 3 ) 3

CD 3

H

CD 3

Ph

1205.

CD 2 C(CH 3 ) 3

H

CD 3

H

Ph

1206.

CD 2 C(CH 3 ) 3

H

H

CD 3

Ph

1207.

CD 2 C(CH 3 ) 3

CD 3

CD 3

H

Ph

1208.

CD 2 C(CH 3 ) 3

CD 3

H

CD 3

Ph

1209.

CD 2 C(CH 3 ) 3

H

CD 3

CD 3

Ph

1210.

CD 2 C(CH 3 ) 3

CD 3

CD 3

CD 3

Ph

1211.

H

CD 2 C(CH 3 ) 3

H

H

Ph

1212.

CD 3

CD 2 C(CH 3 ) 3

H

CD 3

Ph

1213.

H

CD 2 C(CH 3 ) 3

CD 3

H

Ph

1214.

H

CD 2 C(CH 3 ) 3

H

CD 3

Ph

1215.

CD 3

CD 2 C(CH 3 ) 3

CD 3

H

Ph

1216.

CD 3

CD 2 C(CH 3 ) 3

H

CD 3

Ph

1217.

H

CD 2 C(CH 3 ) 3

CD 3

CD 3

Ph

1218.

CD 3

CD 2 C(CH 3 ) 3

CD 3

CD 3

Ph

1219.

H

H

CD 2 C(CH 3 ) 3

H

Ph

1220.

CD 3

H

CD 2 C(CH 3 ) 3

H

Ph

1221.

H

CD 3

CD 2 C(CH 3 ) 3

H

Ph

1222.

H

H

CD 2 C(CH 3 ) 3

CD 3

Ph

1223.

CD 3

CD 3

CD 2 C(CH 3 ) 3

H

Ph

1224.

CD 3

H

CD 2 C(CH 3 ) 3

CD 3

Ph

1225.

H

CD 3

CD 2 C(CH 3 ) 3

CD 3

Ph

1226.

CD 3

CD 3

CD 2 C(CH 3 ) 3

CD 3

Ph

1227.

H

H

H

Ph

1228.

CD 3

H

CD 3

Ph

1229.

H

CD 3

H

Ph

1230.

H

H

CD 3

Ph

1231.

CD 3

CD 3

H

Ph

1232.

CD 3

H

CD 3

Ph

1233.

H

CD 3

CD 3

Ph

1234.

CD 3

CD 3

CD 3

Ph

1235.

H

H

H

Ph

1236.

CD 3

H

CD 3

Ph

1237.

H

CD 3

H

Ph

1238.

H

H

CD 3

Ph

1239.

CD 3

CD 3

H

Ph

1240.

CD 3

H

CD 3

Ph

1241.

H

CD 3

CD 3

Ph

1242.

CD 3

CD 3

CD 3

Ph

1243.

H

H

H

Ph

1244.

CD 3

H

H

Ph

1245.

H

CD 3

H

Ph

1246.

H

H

CD 3

Ph

1247.

CD 3

CD 3

H

Ph

1248.

CD 3

H

CD 3

Ph

1249.

H

CD 3

CD 3

Ph

1250.

CD 3

CD 3

CD 3

Ph

1251.

H

H

H

Ph

1252.

CD 3

H

CD 3

Ph

1253.

H

CD 3

H

Ph

1254.

H

H

CD 3

Ph

1255.

CD 3

CD 3

H

Ph

1256.

CD 3

H

CD 3

Ph

1257.

H

CD 3

CD 3

Ph

1258.

CD 3

CD 3

CD 3

Ph

1259.

H

H

H

Ph

1260.

CH 3

H

CD 3

Ph

1261.

H

CD 3

H

Ph

1262.

H

H

CD 3

Ph

1263.

CD 3

CD 3

H

Ph

1264.

CD 3

H

CD 3

Ph

1265.

H

CD 3

CD 3

Ph

1266.

CH 3

CD 3

CD 3

Ph

1267.

H

H

H

Ph

1268.

CD 3

H

H

Ph

1269.

H

CD 3

H

Ph

1270.

H

H

CD 3

Ph

1271.

CD 3

CD 3

H

Ph

1272.

CD 3

H

CD 3

Ph

1273.

H

CD 3

CD 3

Ph

1274.

CD 3

CD 3

CD 3

Ph

1275.

H

H

H

Ph

1276.

CD 3

H

CD 3

Ph

1277.

H

CD 3

H

Ph

1278.

H

H

CD 3

Ph

1279.

CD 3

CD 3

H

Ph

1280.

CD 3

H

CD 3

Ph

1281.

H

CD 3

CD 3

Ph

1282.

CD 3

CD 3

CD 3

Ph

1283.

H

H

H

Ph

1284.

CD 3

H

CD 3

Ph

1285.

H

CD 3

H

Ph

1286.

H

H

CD 3

Ph

1287.

CD 3

CD 3

H

Ph

1288.

CD 3

H

CD 3

Ph

1289.

H

CD 3

CD 3

Ph

1290.

CD 3

CD 3

CD 3

Ph

1291.

H

H

H

Ph

1292.

CD 3

H

H

Ph

1293.

H

CD 3

H

Ph

1294.

H

H

CD 3

Ph

1295.

CD 3

CD 3

H

Ph

1296.

CD 3

H

CD 3

Ph

1297.

H

CD 3

CD 3

Ph

1298.

CD 3

CD 3

CD 3

Ph

1299.

H

H

H

Ph

1300.

CD 3

H

CD 3

Ph

1301.

H

CD 3

H

Ph

1302.

H

H

CD 3

Ph

1303.

CD 3

CD 3

H

Ph

1304.

CD 3

H

CD 3

Ph

1305.

H

CD 3

CD 3

Ph

1306.

CD 3

CD 3

CD 3

Ph

1307.

H

H

H

Ph

1308.

CD 3

H

CD 3

Ph

1309.

H

CD 3

H

Ph

1310.

H

H

CD 3

Ph

1311.

CD 3

CD 3

H

Ph

1312.

CD 3

H

CD 3

Ph

1313.

H

CD 3

CD 3

Ph

1314.

CD 3

CD 3

CD 3

Ph

1315.

H

H

H

Ph

1316.

CD 3

H

H

Ph

1317.

H

CD 3

H

Ph

1318.

H

H

CD 3

Ph

1319.

CD 3

CD 3

H

Ph

1320.

CD 3

H

CD 3

Ph

1321.

H

CD 3

CD 3

Ph

1322.

CD 3

CD 3

CD 3

Ph

1323.

H

H

H

Ph

1324.

CD 3

H

CD 3

Ph

1325.

H

CD 3

H

Ph

1326.

H

H

CD 3

Ph

1327.

CD 3

CD 3

H

Ph

1328.

CD 3

H

CD 3

Ph

1329.

H

CD 3

CD 3

Ph

1330.

CD 3

CD 3

CD 3

Ph

1331.

H

H

H

Ph

1332.

CD 3

H

CD 3

Ph

1333.

H

CD 3

H

Ph

1334.

H

H

CD 3

Ph

1335.

CD 3

CD 3

H

Ph

1336.

CD 3

H

CD 3

Ph

1337.

H

CD 3

CD 3

Ph

1338.

CD 3

CD 3

CD 3

Ph

1339.

H

H

H

Ph

1340.

CD 3

H

H

Ph

1341.

H

CD 3

H

Ph

1342.

H

H

CD 3

Ph

1343.

CD 3

CD 3

H

Ph

1344.

CD 3

H

CD 3

Ph

1345.

H

CD 3

CD 3

Ph

1346.

CD 3

CD 3

CD 3

Ph

1347.

H

H

H

Ph

1348.

CD 3

H

CD 3

Ph

1349.

H

CD 3

H

Ph

1350.

H

H

CD 3

Ph

1351.

CD 3

CD 3

H

Ph

1352.

CD 3

H

CD 3

Ph

1353.

H

CD 3

CD 3

Ph

1354.

CD 3

CD 3

CD 3

Ph

1355.

H

H

H

Ph

1356.

CD 3

H

CD 3

Ph

1357.

H

CD 3

H

Ph

1358.

H

H

CD 3

Ph

1359.

CD 3

CD 3

H

Ph

1360.

CD 3

H

CD 3

Ph

1361.

H

CD 3

CD 3

Ph

1362.

CD 3

CD 3

CD 3

Ph

1363.

H

H

H

Ph

1364.

CD 3

H

H

Ph

1365.

H

CD 3

H

Ph

1366.

H

H

CH 3

Ph

1367.

CD 3

CD 3

H

Ph

1368.

CD 3

H

CD 3

Ph

1369.

H

CD 3

CD 3

Ph

1370.

CD 3

CD 3

CD 3

Ph

1371.

CD(CH 3 ) 2

H

CD 2 CH 3

H

Ph

1372.

CD(CH 3 ) 2

H

CD(CH 3 ) 2

H

Ph

1373.

CD(CH 3 ) 2

H

CD 2 CH(CH 3 ) 2

H

Ph

1374.

CD(CH 3 ) 2

H

C(CH 3 ) 3

H

Ph

1375.

CD(CH 3 ) 2

H

CD 2 C(CH 3 ) 3

H

Ph

1376.

CD(CH 3 ) 2

H

H

Ph

1377.

CD(CH 3 ) 2

H

H

Ph

1378.

CD(CH 3 ) 2

H

H

Ph

1379.

CD(CH 3 ) 2

H

H

Ph

1380.

CD(CH 3 ) 2

H

H

Ph

1381.

CD(CH 3 ) 2

H

H

Ph

1382.

C(CH 3 ) 3

H

CD 2 CH 3

H

Ph

1383.

C(CH 3 ) 3

H

CD(CH 3 ) 2

H

Ph

1384.

C(CH 3 ) 3

H

CD 2 CH(CH 3 ) 2

H

Ph

1385.

C(CH 3 ) 3

H

C(CH 3 ) 3

H

Ph

1386.

C(CH 3 ) 3

H

CD 2 C(CH 3 ) 3

H

Ph

1387.

C(CH 3 ) 3

H

H

Ph

1388.

C(CH 3 ) 3

H

H

Ph

1389.

C(CH 3 ) 3

H

H

Ph

1390.

C(CH 3 ) 3

H

H

Ph

1391.

C(CH 3 ) 3

H

H

Ph

1392.

C(CH 3 ) 3

H

H

Ph

1393.

CD 2 C(CH 3 ) 3

H

CD 2 CH 3

H

Ph

1394.

CD 2 C(CH 3 ) 3

H

CD(CH 3 ) 2

H

Ph

1395.

CD 2 C(CH 3 ) 3

H

CD 2 CH(CH 3 ) 2

H

Ph

1396.

CD 2 C(CH 3 ) 3

H

C(CH 3 ) 3

H

Ph

1397.

CD 2 C(CH 3 ) 3

H

CD 2 C(CH 3 ) 3

H

Ph

1398.

CD 2 C(CH 3 ) 3

H

H

Ph

1399.

CD 2 C(CH 3 ) 3

H

H

Ph

1400.

CD 2 C(CH 3 ) 3

H

H

Ph

1401.

CD 2 C(CH 3 ) 3

H

H

Ph

1402.

CD 2 C(CH 3 ) 3

H

H

Ph

1403.

CD 2 C(CH 3 ) 3

H

H

Ph

1404.

H

CD 2 CH 3

H

Ph

1405.

H

CD(CH 3 ) 2

H

Ph

1406.

H

CD 2 CH(CH 3 ) 2

H

Ph

1407.

H

C(CH 3 ) 3

H

Ph

1408.

H

CD 2 C(CH 3 ) 3

H

Ph

1409.

H

H

Ph

1410.

H

H

Ph

1411.

H

H

Ph

1412.

H

H

Ph

1413.

H

H

Ph

1414.

H

H

Ph

1415.

H

CD 2 CH 3

H

Ph

1416.

H

CD(CH 3 ) 2

H

Ph

1417.

H

CD 2 CH(CH 3 ) 2

H

Ph

1418.

H

C(CH 3 ) 3

H

Ph

1419.

H

CD 2 C(CH 3 ) 3

H

Ph

1420.

H

H

Ph

1421.

H

H

Ph

1422.

H

H

Ph

1423.

H

H

Ph

1424.

H

H

Ph

1425.

H

H

Ph

1426.

H

CD 2 CH 3

H

Ph

1427.

H

CD(CH 3 ) 2

H

Ph

1428.

H

CD 2 CH(CH 3 ) 2

H

Ph

1429.

H

C(CH 3 ) 3

H

Ph

1430.

H

CD 2 C(CH 3 ) 3

H

Ph

1431.

H

H

Ph

1432.

H

H

Ph

1433.

H

H

Ph

1434.

H

H

Ph

1435.

H

H

Ph

1436.

H

H

Ph

1437.

H

CD 2 CH 3

H

Ph

1438.

H

CD(CH 3 ) 2

H

Ph

1439.

H

CD 2 CH(CH 3 ) 2

H

Ph

1440.

H

C(CH 3 ) 3

H

Ph

1441.

H

CD 2 C(CH 3 ) 3

H

Ph

1442.

H

H

Ph

1443.

H

H

Ph

1444.

H

H

Ph

1445.

H

H

Ph

1446.

H

H

Ph

1447.

H

H

Ph

1448.

H

CD 2 CH 3

H

Ph

1449.

H

CD(CH 3 ) 2

H

Ph

1450.

H

CD 2 CH(CH 3 ) 2

H

Ph

1451.

H

C(CH 3 ) 3

H

Ph

1452.

H

CD 2 C(CH 3 ) 3

H

Ph

1453.

H

H

Ph

1454.

H

H

Ph

1455.

H

H

Ph

1456.

H

H

Ph

1457.

H

H

Ph

1458.

H

H

H

1459.

H

Ph

CD3

H

H

1460.

H

CD3

H

H

1461.

H

CD3

H

H

1462.

H

CD3

H

H

4 . The compound of claim 3 , wherein at least one R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , or R D comprises a moiety selected from the group consisting of silyl, heteroaryl, nitrile, isonitrile, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof.

5 . The compound of claim 3 , wherein L B is selected from the group consisting of L a Aj , L c Aj , L d Aj , and L k , wherein j is an integer from 177 to 192, and k is an integer from 1459 to 1462.

6 . The compound of claim 3 , wherein L A is selected from the group consisting of L a Ai and L c Ai , wherein i is an integer from 1 to 212;

L B is selected from the group consisting of L a Aj , L c Aj , L d Aj , and L k , wherein j is an integer from 177 to 192, and k is an integer from 1459 to 1462; and

at least one R C or R D is selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, partially or fully deuterated variants thereof, partially or fully fluorinated variants thereof, and combinations thereof.

7 . The compound of claim 3 , wherein L A is selected from the group consisting of L a Ai and L c Ai , wherein i is an integer from 1 to 212;

L B is selected from the group consisting of L a Aj , L c Aj , L d Aj , and L k , wherein j is an integer from 177 to 192, and k is an integer from 1459 to 1462; and

L C is selected from the group consisting of L k′ , wherein k′ is an integer from 1459 to 1462.

8 . The compound of claim 3 , wherein L A is selected from the group consisting of L a Ai and L c Ai , wherein i is an integer from 1 to 212;

L B is selected from the group consisting of L k , k is an integer from 1459 to 1462; and

L C is selected from the group consisting of L k′ , wherein k is an integer from 1 to 1458.

9 . A formulation comprising a compound of claim 1 .

10 . The compound of claim 1 , wherein at least one R B is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, and (a) the R B is joined with an adjacent R B that together with the ring coordinated to the Ir atom forms a dibenzofuran or aza-dibenzofuran moiety, or (b) at least one R A1 , R A2 , or R B is a partially or fully deuterated alkyl or partially or fully fluorinated alkyl.

11 . The compound of claim 1 , wherein at least one R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , or R D comprises a moiety selected from the group consisting of heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof.

12 . An organic light emitting device (OLED) comprising:

an anode;

a cathode; and

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

wherein L A is the ligand with substituents R 1 , R 2 , and R 3 ;

wherein L B is the ligand with substituents R A1 , R A2 , and R B ;

wherein L C is the ligand with substituents R C and R D ;

wherein R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D each independently represents mono, to a maximum possible number of substitutions, or no substitution;

wherein L A , L B , and L C are different from each other, and can be connected to each other to form multidentate ligand;

wherein R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein any two or more substituents among R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D are optionally joined or fused into a ring; and

wherein at least one of the following is true:

(i) at least one R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , or R D comprises a moiety selected from the group consisting of heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof; or

(ii) an R B is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, and (a) the R B is joined with an adjacent R B that together with the ring coordinated to the Ir atom forms a dibenzofuran or aza-dibenzofuran moiety, or (b) at least one R A1 , R A2 , or R B is a partially or fully deuterated alkyl or partially or fully fluorinated alkyl.

13 . The OLED of claim 12 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

14 . The OLED of claim 12 , wherein the organic layer further comprises a host, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH−C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , and C n H 2n —Ar 1 , or the host has no substitutions;

wherein n is from 1 to 10; and

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

15 . The OLED of claim 12 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

16 . The OLED of claim 12 , wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.

17 . The OLED of claim 12 , wherein the organic layer further comprises a host, wherein the host comprises a metal complex.

18 . 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, comprising a compound having a formula Ir(L A )(L B )(L C ) selected from

wherein L A is the ligand with substituents R 1 , R 2 , and R 3 ;

wherein L B is the ligand with substituents R A1 , R A2 , and R B ;

wherein L C is the ligand with substituents R C and R D ;

wherein R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D each independently represents mono, to a maximum possible number of substitutions, or no substitution;

wherein L A , L B , and L C are different from each other, and can be connected to each other to form multidentate ligand;

wherein R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

wherein any two or more substituents among R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , and R D are optionally joined or fused into a ring; and

wherein at least one of the following is true:

(i) at least one R 1 , R 2 , R 3 , R A1 , R A2 , R B , R C , or R D comprises a moiety selected from the group consisting of heteroalkyl, arylalkyl, alkoxy, aryloxy, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, partially or fully deuterated variants thereof, and partially or fully fluorinated variants thereof; or

(ii) an R B is substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, and (a) the R B is joined with an adjacent R B that together with the ring coordinated to the Ir atom forms a dibenzofuran or aza-dibenzofuran moiety, or (b) at least one R A1 , R A2 , or R B is a partially or fully deuterated alkyl or partially or fully fluorinated alkyl.

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 5, 2022
From: TSAI, JUI-YI; JI, ZHIQIANG; DYATKIN, ALEXEY BORISOVICH; XIA, CHUANJUN; LIN, CHUN; ZENG, LICHANG; YEAGER, WALTER
To: UNIVERSAL DISPLAY CORPORATION
Reel/Frame 060736/0334 →
Continuity (8)
Continuation 17075989 · Oct 21, 2020
Continuation 15619190 · Jun 9, 2017
Provisional Application 62516329 · Jun 7, 2017
Provisional Application 62480746 · Apr 3, 2017
Provisional Application 62479795 · Mar 31, 2017
Provisional Application 62450848 · Jan 26, 2017
Provisional Application 62352139 · Jun 20, 2016
Related Publication 20230107413A1 · Apr 6, 2023
References Cited (233)
US 4769292A · Tang et al. · 1988 [cited by applicant]
US 5061569A · VanSlyke et al. · 1991 [cited by applicant]
US 5247190A · Friend et al. · 1993 [cited by applicant]
US 5703436A · Forrest et al. · 1997 [cited by applicant]
US 5707745A · Forrest et al. · 1998 [cited by applicant]
US 5834893A · Bulovic et al. · 1998 [cited by applicant]
US 5844363A · Gu et al. · 1998 [cited by applicant]
US 6013982A · Thompson et al. · 2000 [cited by applicant]
US 6087196A · Sturm et al. · 2000 [cited by applicant]
US 6091195A · Forrest et al. · 2000 [cited by applicant]
US 6097147A · Baldo et al. · 2000 [cited by applicant]
US 6294398B1 · Kim et al. · 2001 [cited by applicant]
US 6303238B1 · Thompson et al. · 2001 [cited by applicant]
US 6337102B1 · Forrest et al. · 2002 [cited by applicant]
US 6468819B1 · Kim et al. · 2002 [cited by applicant]
US 6528187B1 · Okada · 2003 [cited by applicant]
US 6687266B1 · Ma et al. · 2004 [cited by applicant]
US 6835469B2 · Kwong et al. · 2004 [cited by applicant]
US 6921915B2 · Takiguchi et al. · 2005 [cited by applicant]
US 7087321B2 · Kwong et al. · 2006 [cited by applicant]
US 7090928B2 · Thompson et al. · 2006 [cited by applicant]
US 7154114B2 · Brooks et al. · 2006 [cited by applicant]
US 7250226B2 · Tokito et al. · 2007 [cited by applicant]
US 7279704B2 · Walters et al. · 2007 [cited by applicant]
US 7332232B2 · Ma et al. · 2008 [cited by applicant]
US 7338722B2 · Thompson et al. · 2008 [cited by applicant]
US 7393599B2 · Thompson et al. · 2008 [cited by applicant]
US 7396598B2 · Takeuchi et al. · 2008 [cited by applicant]
US 7431968B1 · Shtein et al. · 2008 [cited by applicant]
US 7445855B2 · Mackenzie et al. · 2008 [cited by applicant]
US 7534505B2 · Lin et al. · 2009 [cited by applicant]
US 8946697B1 · Ma et al. · 2015 [cited by applicant]
US 9670404B2 · Xia · 2017 [cited by applicant]
US 10355227B2 · Ma et al. · 2019 [cited by applicant]
US 11482683B2 · Tsai · 2022 [cited by examiner]
US 20020034656A1 · Thompson et al. · 2002 [cited by applicant]
US 20020134984A1 · Igarashi · 2002 [cited by applicant]
US 20020158242A1 · Son et al. · 2002 [cited by applicant]
US 20030138657A1 · Li et al. · 2003 [cited by applicant]
US 20030152802A1 · Tsuboyama et al. · 2003 [cited by applicant]
US 20030162053A1 · Marks et al. · 2003 [cited by applicant]
US 20030175553A1 · Thompson et al. · 2003 [cited by applicant]
US 20030230980A1 · Forrest et al. · 2003 [cited by applicant]
US 20040036077A1 · Ise · 2004 [cited by applicant]
US 20040137267A1 · Igarashi · 2004 [cited by examiner]
US 20040137268A1 · Garashi et al. · 2004 [cited by applicant]
US 20040174116A1 · Lu et al. · 2004 [cited by applicant]
US 20050025993A1 · Thompson et al. · 2005 [cited by applicant]
US 20050112407A1 · Ogasawara et al. · 2005 [cited by applicant]
US 20050238919A1 · Ogasawara · 2005 [cited by applicant]
US 20050244673A1 · Satoh et al. · 2005 [cited by applicant]
US 20050260441A1 · Thompson et al. · 2005 [cited by applicant]
US 20050260449A1 · Walters et al. · 2005 [cited by applicant]
US 20060008670A1 · Lin et al. · 2006 [cited by applicant]
US 20060202194A1 · Jeong et al. · 2006 [cited by applicant]
US 20060240279A1 · Adamovich et al. · 2006 [cited by applicant]
US 20060251923A1 · Lin et al. · 2006 [cited by applicant]
US 20060263635A1 · Ise · 2006 [cited by applicant]
US 20060280965A1 · Kwong et al. · 2006 [cited by applicant]
US 20070003789A1 · Kwong · 2007 [cited by examiner]
US 20070190359A1 · Knowles et al. · 2007 [cited by applicant]
US 20070278938A1 · Yabunouchi et al. · 2007 [cited by applicant]
US 20080001530A1 · Ise · 2008 [cited by applicant]
US 20080015355A1 · Schafer et al. · 2008 [cited by applicant]
US 20080018221A1 · Egen et al. · 2008 [cited by applicant]
US 20080106190A1 · Yabunouchi et al. · 2008 [cited by applicant]
US 20080124572A1 · Mizuki et al. · 2008 [cited by applicant]
US 20080220265A1 · Xia et al. · 2008 [cited by applicant]
US 20080297033A1 · Knowles et al. · 2008 [cited by applicant]
US 20090008605A1 · Kawamura et al. · 2009 [cited by applicant]
US 20090009065A1 · Nishimura et al. · 2009 [cited by applicant]
US 20090017330A1 · Wakuma et al. · 2009 [cited by applicant]
US 20090030202A1 · Wakuma et al. · 2009 [cited by applicant]
US 20090039776A1 · Yamada et al. · 2009 [cited by applicant]
US 20090045730A1 · Nishimura et al. · 2009 [cited by applicant]
US 20090045731A1 · Nishimura et al. · 2009 [cited by applicant]
US 20090101870A1 · Prakash et al. · 2009 [cited by applicant]
US 20090108737A1 · Kwong · 2009 [cited by examiner]
US 20090115316A1 · Zheng et al. · 2009 [cited by applicant]
US 20090165846A1 · Johannes et al. · 2009 [cited by applicant]
US 20090167162A1 · Lin et al. · 2009 [cited by applicant]
US 20090179554A1 · Kuma et al. · 2009 [cited by applicant]
US 20100237334A1 · Ma · 2010 [cited by examiner]
US 20100244004A1 · Xia · 2010 [cited by examiner]
US 20100270916A1 · Xia · 2010 [cited by applicant]
US 20110049496A1 · Fukuzaki · 2011 [cited by applicant]
US 20110227049A1 · Xia · 2011 [cited by applicant]
US 20110315933A1 · Stoessel · 2011 [cited by applicant]
US 20130328018A1 · Chen et al. · 2013 [cited by applicant]
US 20130328019A1 · Xia · 2013 [cited by examiner]
US 20140197386A1 · Kim et al. · 2014 [cited by applicant]
US 20140306206A1 · Watanabe et al. · 2014 [cited by applicant]
US 20150069334A1 · Xia et al. · 2015 [cited by applicant]
US 20150357587A1 · Kishino · 2015 [cited by examiner]
US 20150380666A1 · Szigethy · 2015 [cited by applicant]
US 20160133860A1 · Boudreault et al. · 2016 [cited by applicant]
US 20170365800A1 · Tsai · 2017 [cited by applicant]
CN 103804426 · 2014 [cited by applicant]
EP 0650955 · 1995 [cited by applicant]
EP 1725079 · 2006 [cited by applicant]
EP 2034538 · 2009 [cited by applicant]
JP 200511610 · 2005 [cited by applicant]
JP 2007123392 · 2007 [cited by applicant]
JP 2007254297 · 2007 [cited by applicant]
JP 2008074939 · 2008 [cited by applicant]
JP 2014005247A · 2014 [cited by examiner]
JP 2015166336 · 2015 [cited by applicant]
JP 2015173199 · 2015 [cited by applicant]
KR 20150030511 · 2015 [cited by applicant]
WO 0139234 · 2001 [cited by applicant]
WO 0202714 · 2002 [cited by applicant]
WO 02015654 · 2002 [cited by applicant]
WO 03040257 · 2003 [cited by applicant]
WO 03060956 · 2003 [cited by applicant]
WO 2004093207 · 2004 [cited by applicant]
WO 2004107822 · 2004 [cited by applicant]
WO 2005014551 · 2005 [cited by applicant]
WO 2005019373 · 2005 [cited by applicant]
WO 2005030900 · 2005 [cited by applicant]
WO 2005089025 · 2005 [cited by applicant]
WO 2005097942 · 2005 [cited by applicant]
WO 2005123873 · 2005 [cited by applicant]
WO 2006009024 · 2006 [cited by applicant]
WO 2006056418 · 2006 [cited by applicant]
WO 2006072002 · 2006 [cited by applicant]
WO 2006082742 · 2006 [cited by applicant]
WO 2006098120 · 2006 [cited by applicant]
WO 2006100298 · 2006 [cited by applicant]
WO 2006103874 · 2006 [cited by applicant]
WO 2006114966 · 2006 [cited by applicant]
WO 2006132173 · 2006 [cited by applicant]
WO 2007002683 · 2007 [cited by applicant]
WO 2007004380 · 2007 [cited by applicant]
WO 2007063754 · 2007 [cited by applicant]
WO 2007063796 · 2007 [cited by applicant]
WO 2008056746 · 2008 [cited by applicant]
WO 2008101842 · 2008 [cited by applicant]
WO 2008132085 · 2008 [cited by applicant]
WO 2009000673 · 2008 [cited by applicant]
WO 2009003898 · 2009 [cited by applicant]
WO 2009008311 · 2009 [cited by applicant]
WO 2009018009 · 2009 [cited by applicant]
WO 2009021126 · 2009 [cited by applicant]
WO 2009050290 · 2009 [cited by applicant]
WO 2009062578 · 2009 [cited by applicant]
WO 2009063833 · 2009 [cited by applicant]
WO 2009066778 · 2009 [cited by applicant]
WO 2009066779 · 2009 [cited by applicant]
WO 2009086028 · 2009 [cited by applicant]
WO 2009100991 · 2009 [cited by applicant]
WO 2014033050 · 2014 [cited by applicant]
WO 2014112450 · 2014 [cited by applicant]
WO 2014112657 · 2014 [cited by applicant]
WO 2018084189 · 2018 [cited by applicant]
Ishibashi et al., machine translation of JP-2014005247-A (2014) pp. 1-18. (Year: 2014). [cited by examiner]
Lamansky et al., Highly Phosphorescent Bis-Cyclometalated Iridium Complexes: Synthesis, Photophysical Characterization, and Use in Organic Light Emitting Diodes, Journal of the American Chemical Society (2001) vol. 123,… [cited by examiner]
Adachi et al., “Nearly 100% internal phosphorescence efficiency in an organic light emitting device”, Journal of Applied Physcis (2001) vol. 90, No. 10, pp. 5048-5051. (Year: 2001). [cited by examiner]
Ding et al., “Highly efficient phosphorescent bis-cyclometalated iridium complexes based on quinoline ligands”, Synthetic Metals, vol. 155 (2005) p. 539-548. (Year: 2005). [cited by examiner]
Hofbeck et al., “The Triplet State of fac-Ir(ppy)3”, Inorganic Chemistry (2010) vol. 49, pp. 9290-9299. (Year: 2010). [cited by examiner]
Gao et al., Machine Translation of JP-2014005247-A, pp. 1-27. (Year: 2014). [cited by examiner]
Adachi, Chihaya et al., “Organic Electroluminescent Device Having a Hole Conductor as an Emitting Layer,” Appl. Phys. Lett., 55(15): 1489-1491 (1989). [cited by applicant]
Adachi, Chihaya et al., “Nearly 100% Internal Phosphorescence Efficiency in an Organic Light Emitting Device,” J. Appl. Phys., 90(10): 5048-5051 (2001). [cited by applicant]
Adachi, Chihaya et al., “High-Efficiency Red Electrophosphorescence Devices,” Appl. Phys. Lett., 78(11)1622-1624 (2001). [cited by applicant]
Aonuma, Masaki et al., “Material Design of Hole Transport Materials Capable of Thick-Film Formation in Organic Light Emitting Diodes,” Appl. Phys. Lett., 90, Apr. 30, 2007, 183503-1-183503-3. [cited by applicant]
Baldo et al., Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices, Nature, vol. 395, 151-154, (1998). [cited by applicant]
Baldo et al., Very high-efficiency green organic light-emitting devices based on electrophosphorescence, Appl. Phys. Lett., vol. 75, No. 1, 4-6 (1999). [cited by applicant]
Gao, Zhiqiang et al., “Bright-Blue Electroluminescence From a Silyl-Substituted ter-(phenylene-vinylene) derivative,” Appl. Phys. Lett., 74(6): 865-867 (1999). [cited by applicant]
Guo, Tzung-Fang et al., “Highly Efficient Electrophosphorescent Polymer Light-Emitting Devices,” Organic Electronics, 1: 15-20 (2000). [cited by applicant]
Hamada, Yuji et al., “High Luminance in Organic Electroluminescent Devices with Bis(10-hydroxybenzo[h]quinolinato)beryllium as an Emitter,” Chem. Lett., 905-906 (1993). [cited by applicant]
Holmes, R.J. et al., “Blue Organic Electrophosphorescence Using Exothermic Host-Guest Energy Transfer,” Appl. Phys. Lett., 82(15):2422-2424 (2003). [cited by applicant]
Hu, Nan-Xing et al., “Novel High Tg Hole-Transport Molecules Based on Indolo[3,2-b]carbazoles for Organic Light-Emitting Devices,” Synthetic Metals, 111-112:421-424 (2000). [cited by applicant]
Huang, Jinsong et al., “Highly Efficient Red-Emission Polymer Phosphorescent Light-Emitting Diodes Based on Two Novel Tris(1-phenylisoquinolinato-C2,N)iridium(III) Derivatives,” Adv. Mater., 19:739-743 (2007). [cited by applicant]
Huang, Wei-Sheng et al., “Highly Phosphorescent Bis-Cyclometalated Iridium Complexes Containing Benzoimidazole-Based Ligands,” Chem. Mater., 16(12):2480-2488 (2004). [cited by applicant]
Hung, L.S. et al., “Anode Modification in Organic Light-Emitting Diodes by Low-Frequency Plasma Polymerization of CHF3,” Appl. Phys. Lett., 78(5):673-675 (2001). [cited by applicant]
Ikai, Masamichi et al., “Highly Efficient Phosphorescence From Organic Light-Emitting Devices with an Exciton-Block Layer,” Appl. Phys. Lett., 79(2):156-158 (2001). [cited by applicant]
Ikeda, Hisao et al., “P-185 Low-Drive-Voltage OLEDs with a Buffer Layer Having Molybdenum Oxide,” SID Symposium Digest, 37:923-926 (2006). [cited by applicant]
Inada, Hiroshi and Shirota, Yasuhiko, “1,3,5-Tris[4-(diphenylamino)phenyl]benzene and its Methylsubstituted Derivatives as a Novel Class of Amorphous Molecular Materials,” J. Mater. Chem., 3(3):319-320 (1993). [cited by applicant]
Kanno, Hiroshi et al., “Highly Efficient and Stable Red Phosphorescent Organic Light-Emitting Device Using bis[2-(2-benzothiazoyl)phenolato]zinc(II) as host material,” Appl. Phys. Lett., 90:123509-1-123509-3 (2007). [cited by applicant]
Kido, Junji et al., 1,2,4-Triazole Derivative as an Electron Transport Layer in Organic Electroluminescent Devices, Jpn. J. Appl. Phys., 32:L917-L920 (1993). [cited by applicant]
Kuwabara, Yoshiyuki et al., “Thermally Stable Multilayered Organic Electroluminescent Devices Using Novel Starburst Molecules, 4,4′,4″-Tri(N-carbazolyl)triphenylamine (TCTA) and 4,4′,4″-Tris(3-methylphenylphenyl-amino)t… [cited by applicant]
Kwong, Raymond C. et al., “High Operational Stability of Electrophosphorescent Devices,” Appl. Phys. Lett., 81(1)162-164 (2002). [cited by applicant]
Lamansky, Sergey et al., “Synthesis and Characterization of Phosphorescent Cyclometalated Iridium Complexes,” Inorg. Chem., 40(7):1704-1711 (2001). [cited by applicant]
Lee, Chang-Lyoul et al., “Polymer Phosphorescent Light-Emitting Devices Doped with Tris(2-phenylpyridine) Iridium as a Triplet Emitter,” Appl. Phys. Lett., 77(15):2280-2282 (2000). [cited by applicant]
Lo, Shih-Chun et al., “Blue Phosphorescence from Iridium(III) Complexes at Room Temperature,” Chem. Mater., 18(21)5119-5129 (2006). [cited by applicant]
Ma, Yuguang et al., “Triplet Luminescent Dinuclear-Gold(I) Complex-Based Light-Emitting Diodes with Low Turn-On voltage,” Appl. Phys. Lett., 74(10):1361-1363 (1999). [cited by applicant]
Mi, Bao-Xiu et al., “Thermally Stable Hole-Transporting Material for Organic Light-Emitting Diode an Isoindole Derivative,” Chem. Mater., 15(16):3148-3151 (2003). [cited by applicant]
Nishida, Jun-ichi et al., “Preparation, Characterization, and Electroluminescence Characteristics of α-Diimine-type Platinum(II) Complexes with Perfluorinated Phenyl Groups as Ligands,” Chem. Lett., 34(4): 592-593 (2005… [cited by applicant]
Niu, Yu-Hua et al., “Highly Efficient Electrophosphorescent Devices with Saturated Red Emission from a Neutral Osmium Complex,” Chem. Mater., 17(13):3532-3536 (2005). [cited by applicant]
Noda, Tetsuya and Shirota, Yasuhiko, “5,5′-Bis(dimesitylboryl)-2,2′-bithiophene and 5,5″-Bis(dimesitylboryl)-2,2′5′,2″-terthiophene as a Novel Family of Electron-Transporting Amorphous Molecular Materials,” J. Am. Chem.… [cited by applicant]
Okumoto, Kenji et al., “Green Fluorescent Organic Light-Emitting Device with External Quantum Efficiency of Nearly 10%,” Appl. Phys. Lett., 89:063504-1-063504-3 (2006). [cited by applicant]
Palilis, Leonidas C., “High Efficiency Molecular Organic Light-Emitting Diodes Based on Silole Derivatives and Their Exciplexes,” Organic Electronics, 4:113-121 (2003). [cited by applicant]
Paulose, Betty Marie Jennifer S. et al., “First Examples of Alkenyl Pyridines as Organic Ligands for Phosphorescent Iridium Complexes,” Adv. Mater., 16(22):2003-2007 (2004). [cited by applicant]
Ranjan, Sudhir et al., “Realizing Green Phosphorescent Light-Emitting Materials from Rhenium(I) Pyrazolato Diimine Complexes,” Inorg. Chem., 42(4):1248-1255 (2003). [cited by applicant]
Sakamoto, Youichi et al., “Synthesis, Characterization, and Electron-Transport Property of Perfluorinated Phenylene Dendrimers,” J. Am. Chem. Soc., 122(8):1832-1833 (2000). [cited by applicant]
Salbeck, J. et al., “Low Molecular Organic Glasses for Blue Electroluminescence,” Synthetic Metals, 91:209-215 (1997). [cited by applicant]
Shirota, Yasuhiko et al., “Starburst Molecules Based on pi-Electron Systems as Materials for Organic Electroluminescent Devices,” Journal of Luminescence, 72-74:985-991 (1997). [cited by applicant]
Sotoyama, Wataru et al., “Efficient Organic Light-Emitting Diodes with Phosphorescent Platinum Complexes Containing N∧C∧N∧-Coordinating Tridentate Ligand,” Appl. Phys. Lett., 86:153505-1-153505-3 (2005). [cited by applicant]
Sun, Yiru and Forrest, Stephen R., “High-Efficiency White Organic Light Emitting Devices with Three Separate Phosphorescent Emission Layers,” Appl. Phys. Lett., 91:263503-1-263503-3 (2007). [cited by applicant]
T. Östergård et al., “Langmuir-Blodgett Light-Emitting Diodes of Poly(3-Hexylthiophene) Electro-Optical Characteristics Related to Structure,” Synthetic Metals, 88:171-177 (1997). [cited by applicant]
Takizawa, Shin-ya et al., “Phosphorescent Iridium Complexes Based on 2-Phenylimidazo[1,2-α]pyridine Ligands Tuning of Emission Color toward the Blue Region and Application to Polymer Light-Emitting Devices,” Inorg. Chem… [cited by applicant]
Tang, C.W. and VanSlyke, S.A., “Organic Electroluminescent Diodes,” Appl. Phys. Lett., 51(12):913-915 (1987). [cited by applicant]
Tung, Yung-Liang et al., “Organic Light-Emitting Diodes Based on Charge-Neutral Ru II PHosphorescent Emitters,” Adv. Mater., 17(8)1059-1064 (2005). [cited by applicant]
Van Slyke, S. A. et al., “Organic Electroluminescent Devices with Improved Stability,” Appl. Phys. Lett., 69(15):2160-2162 (1996). [cited by applicant]
Wang, Y. et al., “Highly Efficient Electroluminescent Materials Based on Fluorinated Organometallic Iridium Compounds,” Appl. Phys. Lett., 79(4):449-451 (2001). [cited by applicant]
Wong, Keith Man-Chung et al., A Novel Class of Phosphorescent Gold(III) Alkynyl-Based Organic Light-Emitting Devices with Tunable Colour, Chem. Commun., 2906-2908 (2005). [cited by applicant]
Wong, Wai-Yeung, “Multifunctional Iridium Complexes Based on Carbazole Modules as Highly Efficient Electrophosphors,” Angew. Chem. Int. Ed., 45:7800-7803 (2006). [cited by applicant]
Hohenleutner, Andreas et al., “Rapid Combinational Synthesis and Chromatography Based Screening of Phosphorescent Iridium Complexes for Solution Processing”, Adv. Funct. Mater., 2012, 22, 3406-3413. [cited by applicant]
Notice of Reasons for Rejection issued on Oct. 13, 2020 in corresponding Japanese Patent Application No. 2017-119910. [cited by applicant]
Huang, Y., et al., “Bi-substituted Effect on Phenylisoquinoline Iridium(III) Complexes,” Organometallics, 2005, vol. 24, pp. 6230-6238. [cited by applicant]
Wang, B., et al., “Strongly phosphorescent platinum(ii) complexes supported by tetradentate benzazole-containing ligands,” J. Mater. Chem C., 2015, vol. 3, pp. 8212-8218. [cited by applicant]
Jurow, Matthew J. et al., “Understanding and predicting the orientation of heteroleptic phosphors in organic light-emitting materials” Nature Materials, vol. 15, Jan. 2016, pp. 85-91. [cited by applicant]
Graf, A. et al., “Correlating the transition dipole moment orientation of phosphorescent emitter molecules in OLEDs with basic material properties” J. Mater. Chem. C., 2014, 2, 10298-10304. [cited by applicant]
Kim, Kwon-Hyeon et al., “Phosphorescent dye-based supramolecules for high-efficiency organic light-emitting diodes” Nature Communications, 2014, 5, 4769, 1-8. [cited by applicant]
Kim, Kwon-Hyeon et al., “Design of Heteroleptic Ir Complexes with Horizontal Emitting Dipoles for Highly Efficient Organic Light-Emitting Diodes with an External Quantum Efficiency of 38%”, Chem. Mater. 2016, 28, pp. 75… [cited by applicant]
Kim, Kwon-Hyeon et al., “Highly Efficient Organic Light-Emitting Diodes with Phosphorescent Emitters Having High Quantum Yield and Horizontal Orientation of Transition Dipole Moments”, Adv. Mater. 2014, 26, pp. 3844-384… [cited by applicant]
Burke, Christopher S. and Keyes, Tia E. An Efficient Route to Asymmetrically Diconjugated tris(heteroleptic) Complexes of Ru(II), RSC Advances, vol. 6, Jan. 1, 2013, pp. 40869-40877. [cited by applicant]
Xu, Xianbin et al., “Trifunctional IRIII ppy-type asymmetric phosphorescent emitters with ambiopolar features for highly efficient electroluminescent devices” Chem. Commun., 2014, 50, pp. 2473-2476. [cited by applicant]
Xu, Xianbin et al., “tris-Heteroleptic Cyclometalated Iridium(III) Complexes with Ambipolar or Electron Injection/Transport Features for Highly Efficient Electrophosphorescent Devices” Chem. Asian J. 2015, 10, pp. 252-2… [cited by applicant]
Extended European Search Report issued Apr. 11, 2018 for corresponding EP Application No. 17176681.9. [cited by applicant]
Lepeltier, Marc et al., “Tris-cyclometalated Iridium(III) Complexes with Three Different Ligands: a New Example with 2-(2,4-Difluorophenyl)pyridine-Based Complex,” Helvetica Chimica Acta, vol. 97, Issue 7, Jul. 2014, pp… [cited by applicant]
Office Action issued Jun. 3, 2020 for corresponding CN Application No. 201710471274.2. [cited by applicant]
Ija-Ling Liao et al.: “Ir(III)-Based Phosphors with Bipyrazolate Ancillaries; Rational Design, Photophysics, and Applications in Organic Light-Emitting Diodes” Inorganic Chemistry, vol. 54, No. 22, Nov. 16, 2015 (Nov. 1… [cited by applicant]
European Search Report issued Oct. 26, 2017 for corresponding EP Application No. 17176668.6. [cited by applicant]
Choi, Gyeongshin et al., “Hemilabile N-Xylyl-N′-methylperimidine Carbene Iridium Complexes as Catalysts for C—H Activation and Dehydrogenative Silylation: Dual Role of N-Xylyl Moiety for ortho-C—H Bond Activation and Re… [cited by applicant]
Tordera, Daniel et al., “Stable Green Electroluminescence from an Iridium Tris-Heteroleptic Ionic Complex” Chem. Mater. 2012, 24, 1896-1903. [cited by applicant]
Baranoff, Etienne et al., “Acid-Induced Degradation of Phosphorescent Dopants for OLEDs and Its Application to the Synthesis of Tris-heteroleptic Iridium(III) Bis-cyclometalated Complexes” Inorg. Chem. 2012, 51, 215-224. [cited by applicant]
Edkins, Robert M., et al., “The synthesis and photophysics of tris-heteroleptic cyclometalated iridium complexes” Dalton Trans., 2011, 40, 9672-9678. [cited by applicant]
Lepeltier, Marc et al., “Tris-cyclometalated Iridium(III) Complexes with Three Different Ligands: a New Example with 2-(2,4-Difluorophenyl)pyridine-Based Complex” Helvetica Chimica Acta—vol. 97 (2014), 939-956. [cited by applicant]
Park, Gui Youn et al., “Iridium Complexes Containing Three Different Ligands as White OLED Dopants” Molecular Crystals and Liquid Crystals, vol. 462, pp. 179-188, 2007. [cited by applicant]
Felici, Marco et al., “Cationic Heteroleptic Cyclometalated Iridium(III) Complexes Containing Phenyl-Triazole and Triazole-Pyridine Clicked Ligands” Molecules 2010, 15, 2039-2059. [cited by applicant]
Extended European Search Report issued on Nov. 12, 2020 for corresponding European Patent Application No. 20190784.7. [cited by applicant]
European Search Report issued on Oct. 26, 2017 for corresponding European Patent Application No. 17176695.9. [cited by applicant]
Plummer, Edward A. et al., “Electrophosphorescent Devices Based on Cationic Complexes: Control of Switch-on Voltage and Efficiency Through Modification of Charge Injection and Charge Transport”, Adv. Funct. Mater. 2005,… [cited by applicant]