IP Library Granted Patent US 10,340,466
Granted Patent B2
US 10,340,466 · App. 15/361,239 · Granted Jul 2, 2019

Organic metal compound, organic light-emitting devices employing the same

Inventors: Jin-Sheng Lin (Taipei, TW); Yung-Chen Cheng (Changhua, TW); Jia-Lun Liou (Hengshan Township, TW); Pang-Chi Huang (Taoyuan, TW); Cheng-An Wu (New Taipei, TW); Meng-Hao Chang (New Taipei, TW); Bing-Huang Jiang (New Taipei, TW); Han-Cheng Yeh (Taipei, TW); Chun-Neng Ku (Tainan, TW); Mei-Rurng Tseng (Hsinchu, TW); Jung-Yu Liao (Hsinchu County, TW); Jui-Chih Kao (Taoyuan, TW)
Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
H01L51/0085C07F15/0033C09K11/06H01L51/0071H01L51/5012C09K2211/1007C09K2211/1011C09K2211/1033C09K2211/185H01L51/5016
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Quick Facts
Patent No.
US 10,340,466
App. No.
15/361,239
Granted
Jul 2, 2019
Kind
B2
Abstract

Organic metal compounds, and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure represented by Formula (I) or Formula (II): wherein, R 1 is hydrogen, C 1-12 alkyl, C 1-12 alkoxy, amine, C 2-6 alkenyl, C 2-6 alkynyl, C 5-10 cycloalkyl, C 3-12 heteroaryl, or C 6-12 aryl; R 2 , R 3 , R 4 , and R 5 can be hydrogen, halogen, C 1-12 alkyl, C 1-12 alkoxy, C 1-12 fluoroalkyl; R 6 and R 7 are independent and can be C 1-6 alkyl, or phenyl; R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , and R 15 can be hydrogen, halogen, C 1-12 alkyl, C 1-12 fluoroalkyl, or two adjacent groups of R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl; m is 1 or 2; and, n is 0 or 1.

Claims (30)

1. An organic metal compound, having a structure of Formula (I) or Formula (II):

wherein, R 1 is independently hydrogen, C 1-12 alkyl group, C 1-12 alkoxy group, amine, C 2-6 alkenyl group, C 2-6 alkynyl group, C 5-10 cycloalkyl group, C 3-12 heteroaryl group, or C 6-12 aryl group; R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, C 1-12 fluoroalkyl group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; R 6 and R 7 are independent C 1-6 alkyl group, or phenyl group; R 8 , R 9 , R 10 , and R 11 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 fluoroalkyl group, or two adjacent groups of R 8 , R 9 , R 10 , and R 11 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; R 12 , R 13 , R 14 , and R 15 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 fluoroalkyl group, or two adjacent groups of R 12 , R 13 , R 14 , and R 15 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; m is 1 or 2; and, n is 0 or 1.

2. The organic metal compound as claimed in claim 1 , wherein each R 1 is independently hydrogen, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, cyclohexyl group, phenyl group, biphenyl group, or naphthyl group.

3. The organic metal compound as claimed in claim 1 , wherein R 2 , R 3 , R 4 , and R 5 are independently hydrogen, fluorine, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, fluoromethyl, fluoroethyl, methoxy, ethoxy, propoxy, or isopropoxy, or R 3 and R 4 are combined with the carbon atoms which they are attached to, to form a phenyl group.

4. The organic metal compound as claimed in claim 1 , wherein at least one of R 1 , R 2 , R 3 , R 4 , and R 5 is not hydrogen.

5. The organic metal compound as claimed in claim 1 , wherein R 6 and R 7 are independently methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, or phenyl group.

6. The organic metal compound as claimed in claim 1 , wherein R 8 , R 9 , R 10 , and R 11 are independently hydrogen, fluorine, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, fluoromethyl, or fluoroethyl, or R 9 and R 10 are combined with the carbon atoms which they are attached to, to form a phenyl group, and/or R 10 and R 11 are combined with the carbon atoms which they are attached to, to form a phenyl group.

7. The organic metal compound as claimed in claim 1 , wherein R 12 , R 13 , R 14 , and R 15 are independently hydrogen, fluorine, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, fluoromethyl, or fluoroethyl, or R 12 and R 13 are combined with the carbon atoms which they are attached to, to form a phenyl group, and/or R 13 and R 14 are combined with the carbon atoms which they are attached to, to form a phenyl group.

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

R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, C 1-12 fluoroalkyl group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; R 6 and R 7 are independent C 1-6 alkyl group, or phenyl group; and, n is 0 or 1.

9. The organic metal compound as claimed in claim 8 , wherein at least one of R 2 , R 3 , R 4 , and R 5 is not hydrogen.

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

R 1 is independently hydrogen, C 1-12 alkyl group, C 1-12 alkoxy group, amine, C 2-6 alkenyl group, C 2-6 alkynyl group, C 5-10 cycloalkyl group, C 3-12 heteroaryl group, or C 6-12 aryl group; and, R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, C 1-12 fluoroalkyl group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group.

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

R 1 is independently hydrogen, C 1-12 alkyl group, C 1-12 alkoxy group, amine, C 2-6 alkenyl group, C 2-6 alkynyl group, C 5-10 cycloalkyl group, C 3-12 heteroaryl group, or C 6-12 aryl group; and, R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, C 1-12 fluoroalkyl group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group.

12. The organic metal compound as claimed in claim 1 , wherein R 1 is independently hydrogen, or C 1-12 alkyl group; R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form an aryl group; and R 6 and R 7 are independent C 1-6 alkyl group.

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

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

R 1 is independently hydrogen, C 1-12 alkyl group, C 1-12 alkoxy group, amine, C 2-6 alkenyl group, C 2-6 alkynyl group, C 5-10 cycloalkyl group, C 3-12 heteroaryl group, or C 6-12 aryl group; R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, C 1-12 fluoroalkyl group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; and, m is 1 or 2.

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

R 1 is independently hydrogen, C 1-12 alkyl group, C 1-12 alkoxy group, amine, C 2-6 alkenyl group, C 2-6 alkynyl group, C 5-10 cycloalkyl group, C 3-12 heteroaryl group, or C 6-12 aryl group; R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, C 1-12 fluoroalkyl group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; R 8 , R 9 , R 10 , and R 11 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 fluoroalkyl group, or two adjacent groups of R 8 , R 9 , R 10 , and R 11 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; and, m is 1 or 2.

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

R 1 is independently hydrogen, C 1-12 alkyl group, C 1-12 alkoxy group, amine, C 2-6 alkenyl group, C 2-6 alkynyl group, C 5-10 cycloalkyl group, C 3-12 heteroaryl group, or C 6-12 aryl group; R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, C 1-12 fluoroalkyl group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; R 12 , R 13 , R 14 , and R 15 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 fluoroalkyl group, or two adjacent groups of R 12 , R 13 , R 14 , and R 15 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; and, m is 1 or 2.

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

R 1 is independently hydrogen, C 1-12 alkyl group, C 1-12 alkoxy group, amine, C 2-6 alkenyl group, C 2-6 alkynyl group, C 5-10 cycloalkyl group, C 3-12 heteroaryl group, or C 6-12 aryl group; R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, C 1-12 fluoroalkyl group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; R 12 , R 13 , R 14 , and R 15 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 fluoroalkyl group, or two adjacent groups of R 12 , R 13 , R 14 , and R 15 are optionally combined with the carbon atoms which they are attached to, to form a cycloalkyl group, or aryl group; and, m is 1 or 2.

18. The organic metal compound as claimed in claim 1 , wherein R 1 is independently hydrogen, or C 1-12 alkyl group; R 2 , R 3 , R 4 , and R 5 are independently hydrogen, halogen, C 1-12 alkyl group, C 1-12 alkoxy group, or two adjacent groups of R 2 , R 3 , R 4 , and R 5 are optionally combined with the carbon atoms which they are attached to, to form an aryl group; R 8 , R 9 , R 10 , and R 11 are independently hydrogen, C 1-12 alkyl group, or two adjacent groups of R 8 , R 9 , R 10 , and R 11 are optionally combined with the carbon atoms which they are attached to, to form an aryl group; and R 12 , R 13 , R 14 , and R 15 are independently hydrogen, or C 1-12 alkyl group.

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

20. An organic light-emitting device, comprising:

a pair of electrodes; and

an organic light-emitting element, disposed between the 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 Dec 23, 2016
From: LIN, JIN-SHENG; CHENG, YUNG-CHEN; LIOU, JIA-LUN; HUANG, PANG-CHI; WU, CHENG-AN; CHANG, MENG-HAO; JIANG, BING-HUANG; YEH, HAN-CHENG; KU, CHUN-NENG; TSENG, MEI-RURNG; LIAO, JUNG-YU; KAO, JUI-CHIH
To: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE
Reel/Frame 040760/0336 →
Priority Claims (2)
TW 104139355 A · Nov 26, 2015 · national
TW 105136104 A · Nov 7, 2016 · national
Continuity (1)
Related Publication 20170155065A1 · Jun 1, 2017
Cited By (2)
US 12,384,810 US 12,655,167