IP Library › Granted Patent US 11,505,566
Granted Patent B2
US 11,505,566 · App. 16/450,006 · Granted Nov 22, 2022

Organic metal compound and organic light-emitting device

Inventors: Yu-Chieh Pao (Hsinchu, TW); Jia-Lun Liou (Hsinchu County, TW); Han-Cheng Yeh (Taipei, TW); Po-Jung Hsu (Taipei, TW); Mei-Rurng Tseng (Hsinchu, TW)
Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
C07F15/0033H01L51/0085
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Quick Facts
Patent No.
US 11,505,566
App. No.
16/450,006
Granted
Nov 22, 2022
Kind
B2
Abstract

Organic metal compounds and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure of Formula (I) or Formula (II): In particular, one of the following two conditions (1) and (2) is met: (1) R 1 is deuterium or C 1-6 deuterated alkyl group, when R 3 and R 4 are independently hydrogen, halogen, C 1-6 alkyl group, C 1-6 fluoroalkyl or C 3-12 heteroaryl group; and (2) R 1 is hydrogen, deuterium, C 1-6 alkyl group, C 1-6 deuterated alkyl group, C 3-12 heteroaryl group, or C 6-12 aryl group, when at least one of R 3 and R 4 is C 6-12 aryl group or C 6-12 fluoroaryl group.

Claims (18)

1. An organic metal compound, which has a chemical structure of Formula (II):

wherein X is O or S; R 1 is hydrogen or deuterium; R 2 , R 4 and R 5 are hydrogen; R 3 is phenyl group; R 9 , R 10 , R 11 and R 12 are independently hydrogen, halogen, deuterium, C 1-6 alkyl group, C 1-6 deuterated alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11 and R 12 are optionally combined with the carbon atoms which R 9 , R 10 , R 11 and R 12 are attached to, to form an aryl group or a cycloalkyl group, wherein R 13 , R 14 , R 15 and R 16 are independently hydrogen, halogen, C 1-6 alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 and R 16 are optionally combined with the carbon atoms which R 13 , R 14 , R 15 and R 16 are attached to, to form an aryl group or a cycloalkyl group.

2. The organic metal compound as claimed in claim 1 , wherein the organic metal compound is

wherein R 1 is hydrogen or deuterium; R 2 , R 4 and R 5 are hydrogen; R 3 is phenyl group; R 9 , R 10 , R 11 and R 12 are independently hydrogen, halogen, deuterium, C 1-6 alkyl group, C 1-6 deuterated alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11 and R 12 are optionally combined with the carbon atoms which R 9 , R 10 , R 11 and R 12 are attached to, to form an aryl group or a cycloalkyl group; and R 13 , R 14 , R 15 , and R 16 are independently hydrogen, halogen, C 1-6 alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 , and R 16 are optionally combined with the carbon atoms which R 13 , R 14 , R 15 , and R 16 are attached to, to form an aryl group or a cycloalkyl group.

3. The organic metal compound as claimed in claim 2 , wherein the organic metal compound is

R 2 , R 4 and R 5 are hydrogen; R 3 is phenyl group; R 9 , R 10 , R 11 and R 12 are independently hydrogen, halogen, deuterium, C 1-6 alkyl group, C 1-6 deuterated alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11 and R 12 are optionally combined with the carbon atoms which R 9 , R 10 , R 11 and R 12 are attached to, to form an aryl group or a cycloalkyl group; and R 13 , R 14 , R 15 , and R 16 are independently hydrogen, halogen, C 1-6 alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 , and R 16 are optionally combined with the carbon atoms which R 13 , R 14 , R 15 , and R 16 are attached to, to form an aryl group or a cycloalkyl group.

4. The organic metal compound as claimed in claim 2 , wherein the organic metal compound is

wherein R 1 is hydrogen or deuterium; R 2 , R 4 and R 5 are hydrogen; and R 3 is phenyl group.

5. The organic metal compound as claimed in claim 1 , wherein the organic metal compound is

wherein R 1 is hydrogen or deuterium; R 2 , R 4 and R 5 are hydrogen; R 3 is phenyl group; R 9 , R 10 , R 11 and R 12 are independently hydrogen, halogen, deuterium, C 1-6 alkyl group, C 1-6 deuterated alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11 and R 12 are optionally combined with the carbon atoms which R 9 , R 10 , R 11 and R 12 are attached to, to form an aryl group or a cycloalkyl group; and R 13 , R 14 , R 15 , and R 16 are independently hydrogen, halogen, C 1-6 alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 , and R 16 are optionally combined with the carbon atoms which R 13 , R 14 , R 15 , and R 16 are attached to, to form an aryl group or a cycloalkyl group.

6. The organic metal compound as claimed in claim 5 , wherein the organic metal compound is

R 2 , R 4 and R 5 are hydrogen; R 3 is phenyl group; R 9 , R 10 , R 11 and R 12 are independently hydrogen, halogen, deuterium, C 1-6 alkyl group, C 1-6 deuterated alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 9 , R 10 , R 11 and R 12 are optionally combined with the carbon atoms which R 9 , R 10 , R 11 and R 12 are attached to, to form an aryl group or a cycloalkyl group; and R 13 , R 14 , R 15 , and R 16 are independently hydrogen, halogen, C 1-6 alkyl group, C 1-6 fluoroalkyl group, or two adjacent groups of R 13 , R 14 , R 15 , and R 16 are optionally combined with the carbon atoms which R 13 , R 14 , R 15 , and R 16 are attached to, to form an aryl group or a cycloalkyl group.

7. The organic metal compound as claimed in claim 1 , wherein the organic metal compound is

wherein R 1 is hydrogen or deuterium; R 2 , R 4 and R 5 are hydrogen; and R 3 is phenyl group.

8. An organic light-emitting device, comprising:

a pair of electrodes; and

an organic light-emitting element disposed between the pair of electrodes,

wherein the organic light-emitting element comprises the organic metal compound as claimed in claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2019
From: PAO, YU-CHIEH; LIOU, JIA-LUN; YEH, HAN-CHENG; HSU, PO-JUNG; TSENG, MEI-RURNG
To: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
Reel/Frame 049584/0204 →
Priority Claims (1)
TW 107146414 · Dec 21, 2018 · national
Continuity (2)
Provisional Application 62701945 · Jul 23, 2018
Related Publication 20200024294A1 · Jan 23, 2020