IP Library Granted Patent US 9,957,260
Granted Patent B2
US 9,957,260 · App. 14/910,791 · Granted May 1, 2018

Organic metal complex, light emitting material, delayed fluorescent material, and organic light emitting device

Inventors: Yumi Sakai (Kurume, JP); Hiroshi Miyazaki (Kitakyushu, JP); Chihaya Adachi (Fukuoka, JP); Naoto Noutsuka (Fukuoka, JP)
Assignees: KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION; NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.; DYDEN CO.
C07D413/10C07D401/10C07D403/10C07D417/10C07F5/069C09B17/00C09B19/00C09B21/00C09B57/10C09B69/008C09K11/06H01L51/0059H01L51/0077H01L51/0081H01L51/0092C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1096C09K2211/181C09K2211/186C09K2211/188H01L51/5012H01L51/5016
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Quick Facts
Patent No.
US 9,957,260
App. No.
14/910,791
Granted
May 1, 2018
Kind
B2
Abstract

An organic metal complex represented by the following general formula is useful as a light emitting material for an organic electroluminescent device and others. X represents O, S or —N(R 7 )—; Y represents O, S or —N(—SO 2 —R 8 )—; R 1 to R 8 represent H, an alkyl group or an aryl group; at least one of Z 1 and Z 2 represents a phenoxazin-10-yl group, a phenothiazin-10-yl group, a phenazin-10-yl group, etc.; M represents an element of the group 1 except for hydrogen, the group 2, the group 11, the group 12, or the group 13 of the periodic table; L represents a ligand; n is 1 to 3; and m is 0 to 2:

Claims (17)

1. An organic metal complex represented by the following Formula (1):

wherein, in Formula (1), X represents an oxygen atom, a sulfur atom, or —N(R 7 )—; Y represents an oxygen atom, a sulfur atom, or —N(—SO 2 —R 8 )—; R 1 to R 8 each independently represent a hydrogen atom, an alkyl group which may be substituted by an alkoxy group, an aryl group or an aryloxy group, or an aryl group which may be substituted by an alkyl group, an alkoxy group, an aryl group or an aryloxy group; Z 1 and Z 2 each independently represent a hydrogen atom, an alkyl group which may be substituted by an alkoxy group, an aryl group or an aryloxy group, an aryl group which may be substituted by an alkyl group, an alkoxy group, an aryl group or an aryloxy group, or a group represented by any of the following Formulae (A) to (E), provided that at least one of Z 1 and Z 2 represents a group represented by any of the following Formulae (A) to (E); M represents lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, copper, silver, gold, zinc, cadmium, mercury, boron, aluminum, gallium, indium, or thallium; L represents a ligand that is not encompassed by the following formula:

n represents an integer of from 1 to 3; and m represents an integer of from 0 to 2:

wherein, in Formulae (A) to (E), R 21 to R 28 , R 31 to R 38 , R 41 to R 49 , and R 51 to R 70 each independently represent a hydrogen atom or a substituent, provided that R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 25 and R 26 , R 26 and R 27 , R 27 and R 28 , R 31 and R 32 , R 32 and R 33 , R 33 and R 34 , R 35 and R 36 , R 36 and R 37 , R 37 and R 38 , R 41 and R 42 , R 42 and R 43 , R 43 and R 44 , R 45 and R 46 , R 46 and R 47 , R 47 and R 48 R 51 , and R 52 , R 52 and R 53 , R 53 and R 54 , R 55 and R 56 , R 56 and R 57 , R 57 and R 58 , R 59 and R 60 , R 61 and R 62 , R 62 and R 63 , R 63 and R 64 , R 65 and R 66 , R 66 and R 67 , R 67 and R 68 , and R 69 and R 70 each may be bonded to each other to form a cyclic structure.

2. The organic metal complex according to claim 1 , wherein, in Formula (1), Z 2 represents a group represented by any of the Formulae (A) to (E).

3. The organic metal complex according to claim 1 , wherein, in Formula (1), Z 1 represents a group represented by any of the Formulae (A) to (E).

4. The organic metal complex according to claim 1 , wherein, in Formula (1), Z 1 or Z 2 represents a group represented by the Formula (A) or the Formula (B).

5. The organic metal complex according to claim 1 , wherein, in Formula (1), M represents Zn or Li.

6. The organic metal complex according to claim 1 , wherein, in Formula (1), Y represents an oxygen atom.

7. The organic metal complex according to claim 1 , wherein, in Formula (1), m represents 1 or 2.

8. The organic metal complex according to claim 7 , wherein L represents a substituted or unsubstituted aryloxy ligand.

9. The organic metal complex according to claim 8 , wherein L represents an aryloxy ligand substituted with a substituted or unsubstituted diarylamino group.

10. A light emitting material comprising the organic metal complex according to claim 1 .

11. A delayed fluorescent material comprising the organic metal complex according to claim 1 .

12. An organic light emitting device comprising the light emitting material according to claim 10 .

13. The organic light emitting device according to claim 12 , wherein the organic light emitting device emits delayed fluorescent light.

14. The organic light emitting device according to claim 12 , wherein the organic light emitting device is an organic electroluminescent device.

Assignments (6)
NUNC PRO TUNC ASSIGNMENT Recorded Nov 26, 2024
From: DYDEN CO.
To: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.; KYULUX, INC.
Reel/Frame 069403/0819 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 4, 2021
From: KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION
To: KYULUX, INC.
Reel/Frame 058019/0335 →
CHANGE OF ADDRESS Recorded Nov 24, 2020
From: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
To: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
Reel/Frame 054511/0379 →
CHANGE OF NAME Recorded Mar 26, 2019
From: NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.
To: NIPPON STEEL CHEMICAL & MATERIAL CO., LTD.
Reel/Frame 048708/0803 →
CORRECTIVE ASSIGNMENT TO CORRECT THE FIRST NAMED OF THE ASSIGNEE PREVIOUSLY RECORDED ON REEL 038430 FRAME 0924. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Oct 20, 2016
From: SAKAI, SUMI; MIYAZAKI, HIROSHI; ADACHI, CHIHAYA; NOUTSUKA, NAOTO
To: KYUSHI UNIVERSITY, NATIONAL UNIVERSITY CORPORATION; NIPPON STEEL & SUMKIN CHEMICAL CO., LTD.; DYDEN CO.
Reel/Frame 040431/0083 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 1, 2016
From: SAKAI, SUMI; MIYAZAKI, HIROSHI; ADACHI, CHIHAYA; NOUTSUKA, NAOTO
To: KYUSHU UNIVERSITY NATIONAL UNIVERSITY CORPORATION; NIPPON STEEL & SUMKIN CHEMICAL CO., LTD.; DYDEN CO.
Reel/Frame 038430/0924 →
Priority Claims (2)
JP 2013-166915 · Aug 9, 2013 · national
JP 2014-065283 · Mar 27, 2014 · national
Continuity (1)
Related Publication 20160185765A1 · Jun 30, 2016