IP Library › Granted Patent US 11,631,825
Granted Patent B2
US 11,631,825 · App. 17/091,550 · Granted Apr 18, 2023

Organic electroluminescent element and novel iridium complex

Inventors: Kousuke Watanabe (Kanagawa, JP); Yuichirou Itai (Kanagawa, JP)
Assignee: UDC IRELAND LIMITED
H01L51/5012C07F15/0033C09K11/06H01L51/0085H05B33/14C09K2211/1007C09K2211/1029C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 11,631,825
App. No.
17/091,550
Granted
Apr 18, 2023
Kind
B2
Abstract

An iridium complex which has a phenylpyridine bidentate ligand containing a group represented by the following general formula (A): wherein X represents a cyano group or a halogenated alkyl group; L represents a single bond or a divalent linking group; R represents a substituent; n represents an integer of 0 to 4; * represents a binding site to a phenylpyridine bidentate ligand.

Claims (51)

1. A compound represented by the following general formula (1):

wherein R 111 to R 134 each independently represent a hydrogen atom or a substituent;

at least two adjacent groups out of R 111 to R 114 , R 114 and R 115 , at least two adjacent groups out of R 115 to R 118 , at least two adjacent groups out of R 119 to R 122 , R 122 and R 123 , at least two adjacent groups out of R 123 to R 126 , at least two adjacent groups out of R 127 to R 130 , R 130 and R 131 , or at least two adjacent groups out of R 131 to R 134 may be bonded to each other to form a ring;

provided that at least one of R 111 , R 113 , R 114 , R 119 to R 122 , or R 127 to R 130 represents a group represented by the following general formula (A):

X represents a cyano group or a halogenated alkyl group;

L represents a single bond or a divalent linking group;

R represents a substituent, wherein when a plurality of R's are present, they may be the same as or different from each other; and at least two adjacent groups R may be bonded to each other to form a ring;

n represents an integer of 0 to 4; and

* represents a binding site; and

provided that R 112 does not represent a group represented by general formula (A).

2. The compound of claim 1 , wherein L is an arylene group consisting of 1 to 3 benzene rings.

3. The compound of claim 1 , wherein L is represented by one of L1 to L15:

wherein * represents a binding site; and

wherein L1 to L15 may have additional substituents.

4. The compound of claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (4):

wherein R 111 to R 120 , R 122 to R 126 , and R 411 to R 415 each independently represent a hydrogen atom or a substituent, wherein two groups out of R 111 to R 118 may be each the same as or different from each other;

at least two adjacent groups out of R 111 to R 114 , R 114 and R 115 , at least two adjacent groups out of R 115 to R 118 , R 119 and R 120 , R 122 and R 123 , or at least two adjacent groups out of R 123 to R 126 , or at least two adjacent groups out of R 411 to R 415 may be bonded to each other to form a ring; and

L represents a single bond or a divalent linking group;

provided that at least one of R 411 to R 415 represents a cyano group or a halogenated alkyl group.

5. The compound of claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (5)

wherein R 111 , R 112 , R 114 , R 115 to R 126 , and R 511 to R 515 each independently represent a hydrogen atom or a substituent, wherein two groups out of R 111 , R 112 , R 114 to R 118 , and R 511 to R 515 may be each the same as or different from each other;

R 111 and R 112 , R 114 and R 115 , at least two adjacent groups out of R 115 to R 118 , at least two adjacent groups out of R 119 to R 122 , R 122 and R 123 , or at least two adjacent groups out of R 123 to R 126 , or at least two adjacent groups out of R 511 to R 515 may be bonded to each other to form a ring; and

L represents a single bond or a divalent linking group;

provided that at least one of R 511 to R 515 represents a cyano group or a halogenated alkyl group.

6. The compound of claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula:

wherein R 111 , R 112 , R 114 to R 118 , and R 611 to R 615 each independently represent a hydrogen atom or a substituent, wherein two groups out of R 111 , R 112 , R 114 to R 118 , and R 611 to R 615 may be each the same as or different from each other;

R 111 and R 112 , R 114 and Riis, at least two adjacent groups out of R 115 to R 118 , or at least two adjacent groups out of R 611 to R 615 may be bonded to each other to form a ring; and

L represents a single bond or a divalent linking group; provided that at least one of R 611 to R 615 represents a cyano group or a halogenated alkyl group.

7. The compound of claim 1 , wherein X in the general formula (A) is a cyano group.

8. The compound of claim 1 , wherein the halogenated alkyl group is a fluorinated alkyl group.

9. A light emitting layer or thin film comprising a compound of claim 1 .

10. The light emitting layer or thin film according to claim 9 , wherein the compound of general formula (1) is a compound having the structure:

wherein each R independently represents a hydrogen atom or a substituent and when a plurality of R's are present they may be the same as or different from each other; when R is a substituent n represents an integer of 0 to 4; and wherein at least two adjacent groups R may be bonded to each other to form a ring.

11. The light emitting layer or thin film of claim 9 , further comprising at least one other light emitting material different from the compound represented by general formula 1.

12. An organic electroluminescence element, comprising:

a substrate;

a pair of electrodes including an anode and a cathode, disposed on the substrate; and

at least one organic layer including a light emitting layer, disposed between the electrodes;

wherein at least one compound represented by the following general formula (1) is contained in at least one of the organic layers:

wherein R 111 to R 134 each independently represent a hydrogen atom or a substituent;

at least two adjacent groups out of R 111 to R 114 , R 114 and R 115 , at least two adjacent groups out of R 115 to R 118 , at least two adjacent groups out of R 119 to R 122 , R 122 and R 123 , at least two adjacent groups out of R 123 to R 126 , at least two adjacent groups out of R 127 to R 130 , R 130 and R 131 , or at least two adjacent groups out of R 131 to R 134 may be bonded to each other to form a ring;

provided that at least one of R 111 , R 113 , R 114 , R 119 to R 122 , or R 127 to R 130 represents a group represented by the following general formula (A):

X represents a cyano group or a halogenated alkyl group;

L represents a single bond or a divalent linking group;

R represents a substituent, wherein when a plurality of R's are present, they may be the same as or different from each other; and at least two adjacent groups R may be bonded to each other to form a ring;

n represents an integer of 0 to 4; and

* represents a binding site; and

provided that R 112 does not represent a group represented by general formula (A).

13. The organic electroluminescent element according to claim 12 , wherein a compound represented by the general formula (1) is contained in the light emitting layer.

14. The organic electroluminescent element according to claim 13 , further comprising a compound having a cyano group, in addition to the compound represented by the general formula (1), in the light emitting layer.

15. A device comprising the organic electroluminescent element of claim 12 , wherein the device is selected from a light emitting device, a display device, and an illumination device.

Priority Claims (1)
JP 2011- 218507 · Sep 30, 2011 · national
Continuity (3)
Continuation 16458308 · Jul 1, 2019
Continuation 14240109
Related Publication 20210057666A1 · Feb 25, 2021