IP Library Granted Patent US 11,208,368
Granted Patent B2
US 11,208,368 · App. 16/519,939 · Granted Dec 28, 2021

Double-spiro type compound and organic light-emitting device containing same

Inventors: Yongbum Cha (Daejeon, KR); Jin Joo Kim (Daejeon, KR)
Assignee: LG CHEM, LTD.
C07C13/72C07D239/24C07D251/12C09K11/06H01L51/50C07C2603/97
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Quick Facts
Patent No.
US 11,208,368
App. No.
16/519,939
Granted
Dec 28, 2021
Kind
B2
Abstract

The present specification relates to a double spiro structure compound, and an organic light emitting device comprising the same.

Claims (510)

1. A double Spiro structure compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,

R 1 is represented by the following Chemical Formula B,

wherein, in Chemical Formula B,

X 1 to X 3 are the same as or different from each other, and each independently CH or N;

at least one of X 1 to X 3 is N;

L 2 is selected from the group consisting of a direct bond and a monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; and

Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of any one of the following structural formula:

wherein ---- is a linker between substituents.

2. The double spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-3:

wherein, in Chemical Formula 1-1 to Chemical Formula 1-3, a definition of R 1 is the same as in Chemical Formula 1.

3. The double Spiro structure compound of claim 1 , wherein L 2 is selected from the group consisting of a direct bond; a phenylene group; and a biphenylylene group.

4. An organic light emitting device comprising:

an anode;

a cathode provided opposite to the anode; and

a light emitting layer and one or more organic material layers provided between the anode and the cathode,

wherein the light emitting layer or one or more layers of the organic material layers comprise the double spiro structure compound of claim 1 .

5. The organic light emitting device of claim 4 , wherein the organic material layer comprises a hole injection layer or a hole transfer layer, and the hole injection layer or the hole transfer layer comprises the double Spiro structure compound.

6. The organic light emitting device of claim 4 , wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the double Spiro structure compound.

7. The organic light emitting device of claim 4 , wherein the light emitting layer comprises the double spiro structure compound.

8. The organic light emitting device of claim 4 , wherein the organic material layer comprises an electron transfer layer, an electron injection layer or a layer carrying out electron transfer and electron injection at the same time, and the electron transfer layer, the electron injection layer or the layer carrying out electron transfer and electron injection at the same time comprises the double spiro structure compound.

9. A double spiro structure compound represented by Chemical Formula 1:

wherein in Chemical Formula 1,

R 1 is a moiety selected from the group consisting of:

wherein L 2 is selected from the group consisting of a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; and

wherein Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

10. The double spiro structure compound of claim 9 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-1, and in the following Chemical Formula 3-1, L 2 , Ar 3 and Ara are any one selected from among 3-1-1 to 3-1-104 of the following Table 2:

TABLE 2

3-1-1

Direct bond

3-1-2

Direct bond

3-1-3

Direct bond

3-1-4

Direct bond

3-1-5

Direct bond

3-1-6

Direct bond

3-1-7

Direct bond

3-1-8

Direct bond

3-1-9

Direct bond

3-1-10

Direct bond

3-1-11

Direct bond

3-1-12

3-1-13

3-1-14

3-1-15

3-1-16

3-1-17

3-1-18

3-1-19

3-1-20

3-1-21

3-1-22

3-1-23

3-1-24

3-1-25

3-1-26

3-1-27

3-1-28

3-1-29

3-1-30

3-1-31

3-1-32

3-1-33

3-1-34

3-1-35

3-1-36

3-1-37

3-1-38

3-1-39

3-1-40

3-1-41

3-1-42

3-1-43

3-1-44

3-1-45

3-1-46

3-1-47

3-1-48

3-1-49

3-1-50

3-1-51

3-1-52

3-1-53

3-1-54

3-1-55

3-1-56

3-1-57

3-1-58

3-1-59

3-1-60

3-1-61

3-1-62

3-1-63

3-1-64

3-1-65

3-1-66

3-1-67

3-1-68

3-1-69

3-1-70

3-1-71

3-1-72

3-1-73

3-1-74

3-1-75

3-1-76

3-1-77

3-1-78

3-1-79

3-1-80

3-1-81

3-1-82

3-1-83

3-1-84

3-1-85

3-1-86

3-1-87

3-1-88

3-1-89

3-1-90

3-1-91

3-1-92

3-1-93

3-1-94

3-1-95

3-1-96

3-1-97

3-1-98

3-1-99

3-1-100

3-1-101

3-1-102

3-1-103

3-1-104

11. The double spiro structure compound of claim 9 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-2, and in the following Chemical Formula 3-2, L 2 , Ar 3 and Ar 4 are any one selected from among 3-2-1 to 3-2-104 of the following Table 3:

TABLE 3

3-2-1

Direct bond

3-2-2

Direct bond

3-2-3

Direct bond

3-2-4

Direct bond

3-2-5

Direct bond

3-2-6

Direct bond

3-2-7

Direct bond

3-2-8

Direct bond

3-2-9

Direct bond

3-2-10

Direct bond

3-2-11

Direct bond

3-2-12

3-2-13

3-2-14

3-2-15

3-2-16

3-2-17

3-2-18

3-2-19

3-2-20

3-2-21

3-2-22

3-2-23

3-2-24

3-2-25

3-2-26

3-2-27

3-2-28

3-2-29

3-2-30

3-2-31

3-2-32

3-2-33

3-2-34

3-2-35

3-2-36

3-2-37

3-2-38

3-2-39

3-2-40

3-2-41

3-2-42

3-2-43

3-2-44

3-2-45

3-2-46

3-2-47

3-2-48

3-2-49

3-2-50

3-2-51

3-2-52

3-2-53

3-2-54

3-2-55

3-2-56

3-2-57

3-2-58

3-2-59

3-2-60

3-2-61

3-2-62

3-2-63

3-2-64

3-2-65

3-2-66

3-2-67

3-2-68

3-2-69

3-2-70

3-2-71

3-2-72

3-2-73

3-2-74

3-2-75

3-2-76

3-2-77

3-2-78

3-2-79

3-2-80

3-2-81

3-2-82

3-2-83

3-2-84

3-2-85

3-2-86

3-2-87

3-2-88

3-2-89

3-2-90

3-2-91

3-2-92

3-2-93

3-2-94

3-2-95

3-2-96

3-2-97

3-2-98

3-2-99

3-2-100

3-2-101

3-2-102

3-2-103

3-2-104

12. The double spiro structure compound of claim 9 , wherein in the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-3, and in the following Chemical Formula 3-3, L 2 , Ar 3 and Ar 4 are any one selected from among 3-3-1 to 3-3-104 of the following Table 4:

TABLE 4

---L 2 ---

---Ar 3

---Ar 4

3-3-1

Direct bond

3-3-2

Direct bond

3-3-3

Direct bond

3-3-4

Direct bond

3-3-5

Direct bond

3-3-6

Direct bond

3-3-7

Direct bond

3-3-8

Direct bond

3-3-9

Direct bond

3-3-10

Direct bond

3-3-11

Direct bond

3-3-12

3-3-13

3-3-14

3-3-15

3-3-16

3-3-17

3-3-18

3-3-19

3-3-20

3-3-21

3-3-22

3-3-23

3-3-24

3-3-25

3-3-26

3-3-27

3-3-28

3-3-29

3-3-30

3-3-31

3-3-32

3-3-33

3-3-34

3-3-35

3-3-36

3-3-37

3-3-38

3-3-39

3-3-40

3-3-41

3-3-42

3-3-43

3-3-44

3-3-45

3-3-46

3-3-47

3-3-48

3-3-49

3-3-50

3-3-51

3-3-52

3-3-53

3-3-54

3-3-55

3-3-56

3-3-57

3-3-58

3-3-59

3-3-60

3-3-61

3-3-62

3-3-63

3-3-64

3-3-65

3-3-66

3-3-67

3-3-68

3-3-69

3-3-70

3-3-71

3-3-72

3-3-73

3-3-74

3-3-75

3-3-76

3-3-77

3-3-78

3-3-79

3-3-80

3-3-81

3-3-82

3-3-83

3-3-84

3-3-85

3-3-86

3-3-87

3-3-88

3-3-89

3-3-90

3-3-91

3-3-92

3-3-93

3-3-94

3-3-95

3-3-96

3-3-97

3-3-98

3-3-99

3-3-100

3-3-101

3-3-102

3-3-103

3-3-104

13. The double spiro structure compound of claim 9 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-4, and in the following Chemical Formula 3-4, L 2 , Ar 3 and Ar 4 are any one selected from among 3-4-1 to 3-4-104 of the following Table 5:

TABLE 5

---L 2 ---

---Ar 3

---Ar 4

3-4-1

Direct bond

3-4-2

Direct bond

3-4-3

Direct bond

3-4-4

Direct bond

3-4-5

Direct bond

3-4-6

Direct bond

3-4-7

Direct bond

3-4-8

Direct bond

3-4-9

Direct bond

3-4-10

Direct bond

3-4-11

Direct bond

3-4-12

3-4-13

3-4-14

3-4-15

3-4-16

3-4-17

3-4-18

3-4-19

3-4-20

3-4-21

3-4-22

3-4-23

3-4-24

3-4-25

3-4-26

3-4-27

3-4-28

3-4-29

3-4-30

3-4-31

3-4-32

3-4-33

3-4-34

3-4-35

3-4-36

3-4-37

3-4-38

3-4-39

3-4-40

3-4-41

3-4-42

3-4-43

3-4-44

3-4-45

3-4-46

3-4-47

3-4-48

3-4-49

3-4-50

3-4-51

3-4-52

3-4-53

3-4-54

3-4-55

3-4-56

3-4-57

3-4-58

3-4-59

3-4-60

3-4-61

3-4-62

3-4-63

3-4-64

3-4-65

3-4-66

3-4-67

3-4-68

3-4-69

3-4-70

3-4-71

3-4-72

3-4-73

3-4-74

3-4-75

3-4-76

3-4-77

3-4-78

3-4-79

3-4-80

3-4-81

3-4-82

3-4-83

3-4-84

3-4-85

3-4-86

3-4-87

3-4-88

3-4-89

3-4-90

3-4-91

3-4-92

3-4-93

3-4-94

3-4-95

3-4-96

3-4-97

3-4-98

3-4-99

3-4-100

3-4-101

3-4-102

3-4-103

3-4-104

14. An organic light emitting device comprising:

an anode;

a cathode provided opposite to the anode; and

a light emitting layer and one or more organic material layers provided between the cathode and the light emitting layer;

wherein the light emitting layer or the one or more organic material layers comprises the double spiro structure compound of claim 9 .

15. An organic light emitting device comprising:

an anode;

a cathode provided opposite to the anode; and

a light emitting layer and one or more organic material layers provided between the anode and the cathode,

wherein the light emitting layer or the one or more organic material layers comprises the double spiro compound of claim 9 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 23, 2019
From: CHA, YONGBUM; KIM, JIN JOO
To: LG CHEM, LTD.
Reel/Frame 049840/0975 →
Priority Claims (1)
KR 10-2015-0023506 · Feb 16, 2015 · national
Continuity (2)
Division 15545577
Related Publication 20190345082A1 · Nov 14, 2019
Cited By (1)
US 12,652,951