Iridium organometallic complex containing a substituted dibenzo[f,h]quinoxaline and an electronic device having an emitting layer containing the iridium complex

1. A compound of formula (I)

wherein

R 1 is H, C 3 -C 8 cycloalkyl, or C 1 -C 8 alkyl; wherein the C 3 -C 8 cycloalkyl may optionally be substituted by C 1 -C 8 alkyl, or C 1 -C 8 perfluoroalkyl; and

R 2 is H, or C 1 -C 8 alkyl;

or

R 1 is a group of formula

and R 2 is H;

R 4 is C 1 -C 8 alkyl, CF 3 , or NR 7 R 9 ;

R 4 ′ is H, CF 3 or C 1 -C 8 alkyl;

R 4 ″ is C 1 -C 8 alkyl, or CF 3 ;

R 7 and R 9 are independently of each other

 or

R 7 and R 9 together with the nitrogen atom to which they are bonded form a group of formula

R 10 is H, or C 1 -C 8 alkyl;

R 3 and R 8 are independently of each other C 1 -C 8 alkyl, —Si(C 1 -C 8 alkyl) 3 , or C 3 -C 8 cycloalkyl;

M is Ir; and

L is a monodentate ligand selected from the group consisting of a halide anion, nitrate, sulfate, a hexahaloantimonate anion, an alkoxide anion, a carboxylate anion, a thiocarboxylate anion, a dithiocarboxylate anion, a sulfonate anion, a thiolate anion, a carbamate anion, a dithiocarbamate anion, a thiocarbazone anion and a sulfonamide anion, or a bidentate ligand selected from the group consisting of

wherein

R 11 and R 15 are independently of each other hydrogen, C 1 -C 8 alkyl, C 1 -C 8 perfluoroalkyl, or C 2 -C 10 heteroaryl; C 6 -C 18 aryl, which may optionally be substituted by C 1 -C 8 alkyl; or cyclopentyl or cyclohexyl, each of which may optionally be substituted by C 1 -C 8 alkyl, or phenyl;

R 12 and R 16 are independently of each other hydrogen, C 6 -C 18 aryl, or C 1 -C 8 alkyl, or

R 12 is a group of formula

R 13 and R 17 are independently of each other hydrogen, C 1 -C 8 alkyl, C 6 -C 18 aryl, C 2 -C 10 heteroaryl, C 1 -C 8 perfluoroalkyl, or C 1 -C 8 alkoxy, and

R 14 is C 1 -C 8 alkyl, C 6 -C 10 aryl, or C 7 -C 11 aralkyl,

R 18 is C 6 -C 10 aryl,

R 19 is C 1 -C 8 alkyl, or C 1 -C 8 perfluoroalkyl,

R 20 is hydrogen, C 1 -C 8 alkyl, or C 6 -C 10 aryl,

R 21 is hydrogen; or C 1 -C 8 alkyl or C 1 -C 8 alkoxy, each of which may be partially or fully fluorinated;

R 22 and R 23 are independently of each other C q H 2q+1 , C q F 2q+1 , C 6 H 5 , or C 6 F 5 ;

each R 24 is independently hydrogen, C q H 2q+1 , or C q F 2q+1 ;

R 46 is C 1 -C 8 alkyl; or C 6 -C 18 aryl, which may optionally be substituted by C 1 -C 8 alkyl;

q is 1 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24, and p is 2, or 3; or

L is a bidentate ligand L″ selected from the group consisting of

with the proviso that (i) if L is a monodentate ligand, m is 0, 2 or 4, and n is 1, 2 or 3; and (ii) if L is a bidentate ligand, m is 0, 1 or 2, and n is 1, 2 or 3.

2. The compound according to claim 1 , having a structure (Va), structure (Vb), or structure (Vc), below:

wherein

M 2 is Ir;

L is a bidentate ligand selected from the group consisting of

wherein

R 11 and R 15 are independently of each other hydrogen, C 1 -C 8 alkyl, C 1 -C 8 perfluoroalkyl, or C 2 -C 10 heteroaryl; C 6 -C 18 aryl, which may optionally be substituted by C 1 -C 8 alkyl; or cyclopentyl or cyclohexyl, each of which may optionally be substituted by C 1 -C 8 alkyl, or phenyl;

R 12 and R 16 are independently of each other hydrogen, C 6 -C 18 aryl, or C 1 -C 8 alkyl, or

R 12 is a group of formula

R 13 and R 17 are independently of each other hydrogen, C 1 -C 8 alkyl, C 6 -C 18 aryl, C 2 -C 10 heteroaryl, C 1 -C 8 perfluoroalkyl, or C 1 -C 8 alkoxy, and

R 14 is C 1 -C 8 alkyl, C 6 -C 10 aryl, or C 7 -C 11 aralkyl,

R 18 is C 6 -C 10 aryl,

R 19 is C 1 -C 8 alkyl, or C 1 -C 8 perfluoroalkyl,

R 20 is hydrogen, C 1 -C 8 alkyl, or C 6 -C 10 aryl,

R 21 is hydrogen; or C 1 -C 8 alkyl or C 1 -C 8 alkoxy, each of which may be partially or fully fluorinated;

R 22 and R 23 are independently of each other C q H 2q+1 , C q F 2q+1 , C 6 H 5 , or C 6 F 5 ;

each R 24 is independently hydrogen, C q H 2q+1 , or C q F 2q+1 ;

R 46 is C 1 -C 8 alkyl; or C 6 -C 18 aryl, which may optionally be substituted by C 1 -C 8 alkyl;

q is 1 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23 or 24, and p is 2, or 3; and

L″′ is a monodentate ligand selected from the group consisting of a halide anion, nitrate, sulfate, a hexahaloantimonate anion, an alkoxide anion, a carboxylate anion, a thiocarboxylate anion, a dithiocarboxylate anion, a sulfonate anion, a thiolate anion, a carbamate anion, a dithiocarbamate anion, a thiocarbazone anion and a sulfonamide anion.

3. The compound according to claim 1 , wherein R 1 is C 1 -C 8 alkyl or C 3 -C 8 cycloalkyl, wherein the C 3 -C 8 cycloalkyl may optionally be substituted by one, two, three or four C 1 -C 8 alkyl or C 1 -C 8 perfluoroalkyl.

4. The compound according to claim 1 , wherein R 1 is a group of formula

R 4 is C 1 -C 8 alkyl, CF 3 , or NR 7 R 9 ;

R 4 ″ is C 1 -C 8 alkyl, or CF 3 ;

R 7 and R 9 are independently of each other

 or

R 7 and R 9 together with the nitrogen atom to which they are bonded form a group of formula

R 10 is H, or C 1 -C 8 alkyl; and

R 2 is H.

5. The compound according to claim 1 , wherein R 3 and R 8 are independently of each other C 1 -C 8 alkyl, —Si(C 1 -C 4 alkyl) 3 , or C 3 -C 6 cycloalkyl.

6. The compound according to claim 1 , which is a compound of formula

wherein M 2 is Ir;

R 1 is C 1 -C 8 alkyl;

R 2 is H;

R 3 and R 8 are each independently of each other C 1 -C 8 alkyl, —Si(C 1 -C 4 alkyl) 3 , or C 3 -C 6 cycloalkyl; and

L is

7. The compound according to claim 1 , which is a compound of formula

wherein M 2 is Ir;

R 1 is a group of formula

R 2 is H;

R 4 is C 1 -C 8 alkyl, CF 3 , or NR 7 R 9 ;

R 4 ′ is H, CF 3 or C 1 -C 8 alkyl;

R 4 ″ is C 1 -C 8 alkyl, or CF 3 ;

R 7 and R 9 are independently of each other

 or

R 7 and R 9 together with the nitrogen atom to which they are bonded form a group of formula

R 10 is H, or C 1 -C 8 alkyl;

R 3 and R 8 are independently of each other C 1 -C 8 alkyl, —Si(C 1 -C 4 alkyl) 3 , or C 3 -C 6 cycloalkyl;and

L is

8. The compound according to claim 1 , having a formula selected from the following formulae:

Cpd.

L

R 1

R 2

R 3 and R 8

A-1

A 1)

H

H

—CH 3

A-2

A 1)

—CH 3

H

—CH 3

A-3

A 1)

—CH 2 CH 3

H

—CH 3

A-4

A 1)

n-propyl

H

—CH 3

A-5

A 1)

iso-propyl

H

—CH 3

A-6

A 1)

n-butyl

H

—CH 3

A-7

A 1)

sec-butyl

H

—CH 3

A-9

A 1)

iso-butyl

H

—CH 3

A-10

A 1)

tert-butyl

H

—CH 3

A-11

A 1)

neopentyl

H

—CH 3

A-12

A 1)

2-ethylhexyl

H

—CH 3

A-13

A 1)

cyclopentyl

H

—CH 3

A-14

A 1)

cyclohexyl

H

—CH 3

A-16

A 1)

H

H

—CH 2 CH 3

A-17

A 1)

—CH 3

H

—CH 2 CH 3

A-18

A 1)

—CH 2 CH 3

H

—CH 2 CH 3

A-19

A 1)

n-propyl

H

—CH 2 CH 3

A-20

A 1)

iso-propyl

H

—CH 2 CH 3

A-21

A 1)

n-butyl

H

—CH 2 CH 3

A-22

A 1)

sec-butyl

H

—CH 2 CH 3

A-23

A 1)

iso-butyl

H

—CH 2 CH 3

A-24

A 1)

tert-butyl

H

—CH 2 CH 3

A-25

A 1)

neopentyl

H

—CH 2 CH 3

A-26

A 1)

2-ethylhexyl

H

—CH 2 CH 3

A-27

A 1)

cyclopentyl

H

—CH 2 CH 3

A-28

A 1)

cyclohexyl

H

—CH 2 CH 3

A-29

A 1)

—(CH 2 ) 4 —

—CH 2 CH 3

A-30

A 1)

H

H

iso-butyl

A-31

A 1)

—CH 3

H

iso-butyl

A-32

A 1)

—CH 2 CH 3

H

iso-butyl

A-33

A 1)

n-propyl

H

iso-butyl

A-34

A 1)

iso-propyl

H

iso-butyl

A-35

A 1)

n-butyl

H

iso-butyl

A-36

A 1)

sec-butyl

H

iso-butyl

A-37

A 1)

iso-butyl

H

iso-butyl

A-38

A 1)

tert-butyl

H

iso-butyl

A-39

A 1)

neopentyl

H

iso-butyl

A-40

A 1)

2-ethylhexyl

H

iso-butyl

A-41

A 1)

cyclopentyl

H

iso-butyl

A-42

A 1)

cyclohexyl

H

iso-butyl

A-43

A 1)

—(CH 2 ) 4 —

iso-butyl

A-44

A 1)

H

H

neopentyl

A-45

A 1)

—CH 3

H

neopentyl

A-46

A 1)

—CH 2 CH 3

H

neopentyl

A-47

A 1)

n-propyl

H

neopentyl

A-48

A 1)

iso-propyl

H

neopentyl

A-49

A 1)

n-butyl

H

neopentyl

A-50

A 1)

sec-butyl

H

neopentyl

A-51

A 1)

iso-butyl

H

neopentyl

A-52

A 1)

tert-butyl

H

neopentyl

A-53

A 1)

neopentyl

H

neopentyl

A-54

A 1)

2-ethylhexyl

H

neopentyl

A-55

A 1)

cyclopentyl

H

neopentyl

A-56

A 1)

cyclohexyl

H

neopentyl

A-58

B 1)

H

H

—CH 3

A-59

B 1)

—CH 3

H

—CH 3

A-60

B 1)

—CH 2 CH 3

H

—CH 3

A-61

B 1)

n-propyl

H

—CH 3

A-62

B 1)

iso-propyl

H

—CH 3

A-63

B 1)

n-butyl

H

—CH 3

A-64

B 1)

sec-butyl

H

—CH 3

A-65

B 1)

iso-butyl

H

—CH 3

A-66

B 1)

tert-butyl

H

—CH 3

A-67

B 1)

neopentyl

H

—CH 3

A-68

B 1)

2-ethylhexyl

H

—CH 3

A-69

B 1)

cyclopentyl

H

—CH 3

A-70

B 1)

cyclohexyl

H

—CH 3

A-72

B 1)

H

H

—CH 2 CH 3

A-73

B 1)

—CH 3

H

—CH 2 CH 3

A-74

B 1)

—CH 2 CH 3

H

—CH 2 CH 3

A-75

B 1)

n-propyl

H

—CH 2 CH 3

A-76

B 1)

iso-propyl

H

—CH 2 CH 3

A-77

B 1)

n-butyl

H

—CH 2 CH 3

A-78

B 1)

sec-butyl

H

—CH 2 CH 3

A-79

B 1)

iso-butyl

H

—CH 2 CH 3

A-80

B 1)

tert-butyl

H

—CH 2 CH 3

A-81

B 1)

neopentyl

H

—CH 2 CH 3

A-82

B 1)

2-ethylhexyl

H

—CH 2 CH 3

A-83

B 1)

cyclopentyl

H

—CH 2 CH 3

A-84

B 1)

cyclohexyl

H

—CH 2 CH 3

A-87

B 1)

H

H

iso-butyl

A-88

B 1)

—CH 3

H

iso-butyl

A-89

B 1)

—CH 2 CH 3

H

iso-butyl

A-90

B 1)

n-propyl

H

iso-butyl

A-91

B 1)

iso-propyl

H

iso-butyl

A-92

B 1)

n-butyl

H

iso-butyl

A-93

B 1)

sec-butyl

H

iso-butyl

A-94

B 1)

iso-butyl

H

iso-butyl

A-95

B 1)

tert-butyl

H

iso-butyl

A-96

B 1)

neopentyl

H

iso-butyl

A-97

B 1)

2-ethylhexyl

H

iso-butyl

A-98

B 1)

cyclopentyl

H

iso-butyl

A-99

B 1)

cyclohexyl

H

iso-butyl

A-101

B 1)

H

H

neopentyl

A-102

B 1)

—CH 3

H

neopentyl

A-103

B 1)

—CH 2 CH 3

H

neopentyl

A-104

B 1)

n-propyl

H

neopentyl

A-105

B 1)

iso-propyl

H

neopentyl

A-106

B 1)

n-butyl

H

neopentyl

A-107

B 1)

sec-butyl

H

neopentyl

A-108

B 1)

iso-butyl

H

neopentyl

A-109

B 1)

tert-butyl

H

neopentyl

A-110

B 1)

neopentyl

H

neopentyl

A-111

B 1)

2-ethylhexyl

H

neopentyl

A-112

B 1)

cyclopentyl

H

neopentyl

A-113

B 1)

cyclohexyl

H

neopentyl

R 3

Cpd.

L

R 1

R 2

and R 8

B-1

A 1)

Ph

H

—CH 3

B-2

A 1)

H

—CH 3

B-3

A 1)

H

—CH 3

B-4

A 1)

H

—CH 3

B-5

A 1)

H

—CH 3

B-6

A 1)

H

—CH 3

B-7

A 1)

H

—CH 3

B-9

A 1)

H

—CH 3

B-10

A 1)

H

—CH 3

B-11

A 1)

H

—CH 3

B-12

A 1)

H

—CH 3

B-13

A 1)

H

—CH 3

B-14

A 1)

H

—CH 3

B-15

A 1)

H

—CH 3

B-16

A 1)

H

—CH 3

B-17

A 1)

H

—CH 3

B-18

A 1)

H

—CH 3

B-19

A 1)

H

—CH 3

B-20

A 1)

Ph

H

—CH 2 CH 3

B-21

A 1)

H

—CH 2 CH 3

B-22

A 1)

H

—CH 2 CH 3

B-23

A 1)

H

—CH 2 CH 3

B-24

A 1)

H

—CH 2 CH 3

B-25

A 1)

H

—CH 2 CH 3

B-26

A 1)

H

—CH 2 CH 3

B-27

A 1)

H

—CH 2 CH 3

B-28

A 1)

H

—CH 2 CH 3

B-29

A 1)

H

—CH 2 CH 3

B-30

A 1)

H

—CH 2 CH 3

B-31

A 1)

H

—CH 2 CH 3

B-32

A 1)

H

—CH 2 CH 3

B-33

A 1)

H

—CH 2 CH 3

B-34

A 1)

H

—CH 2 CH 3

B-35

A 1)

H

—CH 2 CH 3

B-36

A 1)

H

—CH 2 CH 3

B-37

A 1)

H

—CH 2 CH 3

B-38

A 1)

Ph

H

iso-butyl

B-39

A 1)

H

iso-butyl

B-40

A 1)

H

iso-butyl

B-41

A 1)

H

iso-butyl

B-42

A 1)

H

iso-butyl

B-43

A 1)

H

iso-butyl

B-44

A 1)

H

iso-butyl

B-45

A 1)

H

iso-butyl

B-46

A 1)

H

iso-butyl

B-47

A 1)

H

iso-butyl

B-48

A 1)

H

iso-butyl

B-49

A 1)

H

iso-butyl

B-50

A 1)

H

iso-butyl

B-51

A 1)

H

iso-butyl

B-52

A 1)

H

iso-butyl

B-53

A 1)

H

iso-butyl

B-54

A 1)

H

iso-butyl

B-55

A 1)

H

iso-butyl

B-56

A 1)

Ph

H

neopentyl

B-57

A 1)

H

neopentyl

B-58

A 1)

H

neopentyl

B-59

A 1)

H

neopentyl

B-60

A 1)

H

neopentyl

B-61

A 1)

H

neopentyl

B-62

A 1)

H

neopentyl

B-63

A 1)

H

neopentyl

B-64

A 1)

H

neopentyl

B-65

A 1)

H

neopentyl

B-66

A 1)

H

neopentyl

B-67

A 1)

H

neopentyl

B-68

A 1)

H

neopentyl

B-69

A 1)

H

neopentyl

B-70

A 1)

H

neopentyl

B-71

A 1)

H

neopentyl

B-72

A 1)

H

neopentyl

B-73

A 1)

H

neopentyl

B-74

B 1)

Ph

H

—CH 3

B-75

B 1)

H

—CH 3

B-75

B 1)

H

—CH 3

B-76

B 1)

H

—CH 3

B-77

B 1)

H

—CH 3

B-78

B 1)

H

—CH 3

B-79

B 1)

H

—CH 3

B-80

B 1)

H

—CH 3

B-81

B 1)

H

—CH 3

B-82

B 1)

H

—CH 3

B-83

B 1)

H

—CH 3

B-84

B 1)

H

—CH 3

B-85

B 1)

H

—CH 3

B-86

B 1)

H

—CH 3

B-87

B 1)

H

—CH 3

B-88

B 1)

H

—CH 3

B-89

B 1)

H

—CH 3

B-90

B 1)

H

—CH 3

B-91

B 1)

Ph

H

—CH 2 CH 3

B-92

B 1)

H

—CH 2 CH 3

B-93

B 1)

H

—CH 2 CH 3

B-94

B 1)

H

—CH 2 CH 3

B-95

B 1)

H

—CH 2 CH 3

B-96

B 1)

H

—CH 2 CH 3

B-97

B 1)

H

—CH 2 CH 3

B-98

B 1)

H

—CH 2 CH 3

B-99

B 1)

H

—CH 2 CH 3

B-100

B 1)

H

—CH 2 CH 3

B-101

B 1)

H

—CH 2 CH 3

B-102

B 1)

H

—CH 2 CH 3

B-103

B 1)

H

—CH 2 CH 3

B-104

B 1)

H

—CH 2 CH 3

B-105

B 1)

H

—CH 2 CH 3

B-106

B 1)

H

—CH 2 CH 3

B-107

B 1)

H

—CH 2 CH 3

B-108

B 1)

H

—CH 2 CH 3

B-109

B 1)

Ph

H

iso-butyl

B-110

B 1)

H

iso-butyl

B-111

B 1)

H

iso-butyl

B-112

B 1)

H

iso-butyl

B-113

B 1)

H

iso-butyl

B-114

B 1)

H

iso-butyl

B-115

B 1)

H

iso-butyl

B-116

B 1)

H

iso-butyl

B-117

B 1)

H

iso-butyl

B-118

B 1)

H

iso-butyl

B-119

B 1)

H

iso-butyl

B-120

B 1)

H

iso-butyl

B-121

B 1)

H

iso-butyl

B-122

B 1)

H

iso-butyl

B-123

B 1)

H

iso-butyl

B-124

B 1)

H

iso-butyl

B-125

B 1)

H

iso-butyl

B-126

B 1)

H

iso-butyl

B-127

B 1)

Ph

H

neopentyl

B-128

B 1)

H

neopentyl

B-129

B 1)

H

neopentyl

B-130

B 1)

H

neopentyl

B-131

B 1)

H

neopentyl

B-132

B 1)

H

neopentyl

B-133

B 1)

H

neopentyl

B-134

B 1)

H

neopentyl

B-135

B 1)

H

neopentyl

B-136

B 1)

H

neopentyl

B-137

B 1)

H

neopentyl

B-138

B 1)

H

neopentyl

B-139

B 1)

H

neopentyl

B-140

B 1)

H

neopentyl

B-141

B 1)

H

neopentyl

B-142

B 1)

H

neopentyl

B-143

B 1)

H

neopentyl

B-144

B 1)

H

neopentyl

Cpd.

L

R 1

R 2

R 3 and R 8

C-1

A 1)

H

H

cyclopentyl

C-2

A 1)

—CH 3

H

cyclopentyl

C-3

A 1)

—CH 2 CH 3

H

cyclopentyl

C-4

A 1)

n-propyl

H

cyclopentyl

C-5

A 1)

iso-propyl

H

cyclopentyl

C-6

A 1)

n-butyl

H

cyclopentyl

C-7

A 1)

sec-butyl

H

cyclopentyl

C-9

A 1)

iso-butyl

H

cyclopentyl

C-10

A 1)

tert-butyl

H

cyclopentyl

C-11

A 1)

neopentyl

H

cyclopentyl

C-12

A 1)

2-ethylhexyl

H

cyclopentyl

C-13

A 1)

cyclopentyl

H

cyclopentyl

C-14

A 1)

cyclohexyl

H

cyclopentyl

C-16

A 1)

Ph

H

cyclopentyl

C-17

A 1)

H

cyclopentyl

C-18

A 1)

H

cyclopentyl

C-19

A 1)

H

cyclopentyl

C-20

A 1)

H

cyclopentyl

C-21

A 1)

H

cyclopentyl

C-22

A 1)

H

H

cyclobutyl

C-23

A 1)

—CH 3

H

cyclobutyl

C-24

A 1)

—CH 2 CH 3

H

cyclobutyl

C-25

A 1)

n-propyl

H

cyclobutyl

C-26

A 1)

iso-propyl

H

cyclobutyl

C-27

A 1)

n-butyl

H

cyclobutyl

C-28

A 1)

sec-butyl

H

cyclobutyl

C-29

A 1)

iso-butyl

H

cyclobutyl

C-30

A 1)

tent-butyl

H

cyclobutyl

C-31

A 1)

neopentyl

H

cyclobutyl

C-32

A 1)

2-ethylhexyl

H

cyclobutyl

C-33

A 1)

cyclopentyl

H

cyclobutyl

C-34

A 1)

cyclohexyl

H

cyclobutyl

C-36

A 1)

Ph

H

cyclobutyl

C-37

A 1)

H

cyclobutyl

C-38

A 1)

H

cyclobutyl

C-39

A 1)

H

cyclobutyl

C-40

A 1)

H

cyclobutyl

C-41

A 1)

H

cyclobutyl

C-42

A 1)

H

H

cyclopropyl

C-43

A 1)

—CH 3

H

cyclopropyl

C-44

A 1)

—CH 2 CH 3

H

cyclopropyl

C-45

A 1)

n-propyl

H

cyclopropyl

C-46

A 1)

iso-propyl

H

cyclopropyl

C-47

A 1)

n-butyl

H

cyclopropyl

C-48

A 1)

sec-butyl

H

cyclopropyl

C-49

A 1)

iso-butyl

H

cyclopropyl

C-50

A 1)

tert-butyl

H

cyclopropyl

C-51

A 1)

neopentyl

H

cyclopropyl

C-52

A 1)

2-ethylhexyl

H

cyclopropyl

C-53

A 1)

cyclopentyl

H

cyclopropyl

C-54

A 1)

cyclohexyl

H

cyclopentyl

C-56

A 1)

Ph

H

cyclopropyl

C-57

A 1)

H

cyclopropyl

C-58

A 1)

H

cyclopropyl

C-59

A 1)

H

cyclopropyl

C-60

A 1)

H

cyclopropyl

C-61

A 1)

H

cyclopropyl

C-62

B 1)

H

H

cyclopentyl

C-63

B 1)

—CH 3

H

cyclopentyl

C-64

B 1)

—CH 2 CH 3

H

cyclopentyl

C-65

B 1)

n-propyl

H

cyclopentyl

C-66

B 1)

iso-propyl

H

cyclopentyl

C-67

B 1)

n-butyl

H

cyclopentyl

C-68

B 1)

sec-butyl

H

cyclopentyl

C-69

B 1)

iso-butyl

H

cyclopentyl

C-70

B 1)

tert-butyl

H

cyclopentyl

C-71

B 1)

neopentyl

H

cyclopentyl

C-72

B 1)

2-ethylhexyl

H

cyclopentyl

C-73

B 1)

cyclopentyl

H

cyclopentyl

C-74

B 1)

cyclohexyl

H

cyclopentyl

C-75

B 1)

Ph

H

cyclopentyl

C-76

B 1)

H

cyclopentyl

C-77

B 1)

H

cyclopentyl

C-78

B 1)

H

cyclopentyl

C-79

B 1)

H

cyclopentyl

C-80

B 1)

H

cyclopentyl

C-81

B 1)

H

H

cyclobutyl

C-82

B 1)

—CH 3

H

cyclobutyl

C-83

B 1)

—CH 2 CH 3

H

cyclobutyl

C-84

B 1)

n-propyl

H

cyclobutyl

C-85

B 1)

iso-propyl

H

cyclobutyl

C-86

B 1)

n-butyl

H

cyclobutyl

C-87

B 1)

sec-butyl

H

cyclobutyl

C-88

B 1)

iso-butyl

H

cyclobutyl

C-89

B 1)

tert-butyl

H

cyclobutyl

C-90

B 1)

neopentyl

H

cyclobutyl

C-91

B 1)

2-ethylhexyl

H

cyclobutyl

C-92

B 1)

cyclopentyl

H

cyclobutyl

C-93

B 1)

cyclohexyl

H

cyclobutyl

C-95

B 1)

Ph

H

cyclobutyl

C-96

B 1)

H

cyclobutyl

C-97

B 1)

H

cyclobutyl

C-98

B 1)

H

cyclobutyl

C-99

B 1)

H

cyclobutyl

C-100

B 1)

H

cyclobutyl

C-101

B 1)

H

H

cyclopropyl

C-102

B 1)

—CH 3

H

cyclopropyl

C-103

B 1)

—CH 2 CH 3

H

cyclopropyl

C-104

B 1)

n-propyl

H

cyclopropyl

C-105

B 1)

iso-propyl

H

cyclopropyl

C-106

B 1)

n-butyl

H

cyclopropyl

C-107

B 1)

sec-butyl

H

cyclopropyl

C-108

B 1)

iso-butyl

H

cyclopropyl

C-109

B 1)

tert-butyl

H

cyclopropyl

C-110

B 1)

neopentyl

H

cyclopropyl

C-111

B 1)

2-ethylhexyl

H

cyclopropyl

C-112

B 1)

cyclopentyl

H

cyclopropyl

C-113

B 1)

cyclohexyl

H

cyclopentyl

C-115

B 1)

Ph

H

cyclopropyl

C-116

B 1)

H

cyclopropyl

C-117

B 1)

H

cyclopropyl

C-118

B 1)

H

cyclopropyl

C-119

B 1)

H

cyclopropyl

C-120

B 1)

H

cyclopropyl

Cpd.

L

R 1

R 2

R 3 and R 8

D-1

A 1)

H

H

—Si(CH 3 ) 3

D-2

A 1)

—CH 3

H

—Si(CH 3 ) 3

D-3

A 1)

—CH 2 CH 3

H

—Si(CH 3 ) 3

D-4

A 1)

n-propyl

H

—Si(CH 3 ) 3

D-5

A 1)

iso-propyl

H

—Si(CH 3 ) 3

D-6

A 1)

n-butyl

H

—Si(CH 3 ) 3

D-7

A 1)

sec-butyl

H

—Si(CH 3 ) 3

D-9

A 1)

iso-butyl

H

—Si(CH 3 ) 3

D-10

A 1)

tert-butyl

H

—Si(CH 3 ) 3

D-11

A 1)

neopentyl

H

—Si(CH 3 ) 3

D-12

A 1)

2-ethylhexyl

H

—Si(CH 3 ) 3

D-13

A 1)

cyclopentyl

H

—Si(CH 3 ) 3

D-14

A 1)

cyclohexyl

H

—Si(CH 3 ) 3

D-16

A 1)

Ph

H

—Si(CH 3 ) 3

D-17

A 1)

H

—Si(CH 3 ) 3

D-18

A 1)

H

—Si(CH 3 ) 3

D-19

A 1)

H

—Si(CH 3 ) 3

D-20

A 1)

H

—Si(CH 3 ) 3

D-21

A 1)

H

—Si(CH 3 ) 3

D-22

B 1)

H

H

—Si(CH 3 ) 3

D-23

B 1)

—CH 3

H

—Si(CH 3 ) 3

D-24

B 1)

—CH 2 CH 3

H

—Si(CH 3 ) 3

D-25

B 1)

n-propyl

H

—Si(CH 3 ) 3

D-26

B 1)

iso-propyl

H

—Si(CH 3 ) 3

D-27

B 1)

n-butyl

H

—Si(CH 3 ) 3

D-28

B 1)

sec-butyl

H

—Si(CH 3 ) 3

D-29

B 1)

iso-butyl

H

—Si(CH 3 ) 3

D-30

B 1)

tert-butyl

H

—Si(CH 3 ) 3

D-31

B 1)

neopentyl

H

—Si(CH 3 ) 3

D-32

B 1)

2-ethylhexyl

H

—Si(CH 3 ) 3

D-33

B 1)

cyclopentyl

H

—Si(CH 3 ) 3

D-34

B 1)

cyclohexyl

H

—Si(CH 3 ) 3

D-36

B 1)

Ph

H

—Si(CH 3 ) 3

D-37

B 1)

H

—Si(CH 3 ) 3

D-38

B 1)

H

—Si(CH 3 ) 3

D-39

B 1)

H

—Si(CH 3 ) 3

D-40

B 1)

H

—Si(CH 3 ) 3

D-41

B 1)

H

—Si(CH 3 ) 3

where

A 1) is

and

B is

9. An emitting layer comprising the compound according to claim 1 .

10. The emitting layer according to claim 9 , further comprising a host material.

11. An organic electronic device comprising the compound according to claim 1 .

12. The organic electronic device according to claim 11 , selected from the group consisting of an electrophotographic photoreceptor, a photoelectric converter, an organic solar cell, a switching element, an organic light emitting field effect transistor, an image sensor, a dye laser and an electroluminescent device.

13. An apparatus comprising the organic electronic device according to claim 11 , selected from the group consisting of a stationary visual display unit, a keyboard, a wallpaper, an illumination unit, an item of clothing and an item of furniture.