Tridentate cyclometalated metal complexes with six-membered coordination rings

Patent metadata

Field	Value
Publication number	US-10411202-B2
Application number	US-201815989356-A
Country	US
Kind code	B2
Filing date	May 25, 2018
Priority date	Jul 28, 2014
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

Tridentate cyclometalated complexes with rigid six-membered coordination rings of General Formula I having tunable emission wavelengths in the visible range. These emitters are suitable for full color displays and lighting applications.

First claim

What is claimed is:

1. A complex represented by Formula 5:

wherein:
M is Pt(II), Pd(II), Ir(I), Rh(I), or Au(II),
x=0 or 1, and when x=0, Y 3e is directly linked to Y 3b ;
y=0 or 1, and when y=0, Y 2a is directly linked to Y 4b ;
z=0 or 1, and when m=0, Y 2c is directly linked to Y 2d ;
each of Ar 1 , Ar 2 , and Ar 3 independently represents five-membered heteroaryl or six-membered aryl or heteroaryl,
each n is independently an integer of 1 to 4, valency permitting,
p is 4,
each R 1 , R 2 , R 3 , R 5 , and R 6 is independently hydrogen, halogen, hydroxyl, amino, nitro, thiol, or substituted or unsubstituted alkyl, alkoxyl, alkenyl, alkynyl, heteroaryl, or aryl, and any two of R 1 , any two of R 2 , any two of R 3 , any two of R 5 , and any two of R 6 are optionally linked together,
Y 1a is O, S, NR 2a , C, CR 2a , CR 2b R 2c , PR 2a , AsR 2a , BR 2a , or SiR 2d R 2e , where each of R 2a , R 2b , R 2c , R 2d , and R 2e is independently hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl;
Y 1b is O, S, NR 3a , C, CR 3a , CR 3b R 3c , PR 2a , AsR 2a , BR 2a , P(O)R 2a , AS(O)R 2a , or SiR 3d R 3e , where each of R 3a , R 3b , R 3c , R 3d , and R 3e is independently hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl,
each of Y 2a and Y 2d is independently C, N, NR 4a , or CR 4b , where each of R 4a and R 4b is independently hydrogen, hydroxyl, amino, nitro, thiol, or substituted or unsubstituted C 1 -C 4 alkyl, alkoxy, or aryl;
each of Y 2b and Y 2c is independently C or N,
each of Y 3a , Y 3b , Y 3c , Y 3d and Y 3e is independently C, N, O, S, NR 5a , PR 5b , AsR 5c , SiR 5d R 5e , BR 5f , or CR 5g , where each of R 5a , R 5b , R 5c , R 5d , R 5e , R 5f , and R 5g is independently hydrogen or substituted or unsubstituted C 1 -C 4 alkyl or aryl; or ZR 6a R 6b ; Z is C or Si; and each of R 6a and R 6b is independently substituted or unsubstituted C 1 -C 4 alkyl or aryl,
each of Y 4a , Y 4b , Y 4c , and Y 4d is independently N, NR 4e , C, or CR 4f , where each of R 4e and R 4f is independently hydrogen, hydroxyl, amino, nitro, thiol, or substituted or unsubstituted C 1 -C 4 alkyl, alkoxy, or aryl,
Y is halogen, OCOR 7a , OR 7b , SR 7c , NR 7d R 7e , CO, NR 7f , PR 7g , AsR 7h R 7i R 7j , C≡CR 7k , substituted or unsubstituted: pyridine, imidazole, pyrazole, oxazole, thiazole, isoxazole, or quinoline, where each of R 7a , R 7b , R 7c , R 7d , R 7e , R 7f , R 7g , R 7h , R 7i , R 7j and R 7k is independently, acetylacetonate, pyridine, imidazole or substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, or trisubstituted phosphine.

2. The complex of claim 1 , wherein the complex is represented by one of the following structures:

wherein:
U is O, S, NR, PR, AsR, CR 2 , SiR 2 , or BR,
M is Pt(II) or Pd(II);
each R is independently hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl; and
each Ar 1 is independently selected from the group consisting of substituted or unsubstituted aryl and heteroaryl.

3. The complex of claim 1 , wherein the complex is represented by one of the following structures:

wherein:
U is O, S, NR, PR, AsR, CR 2 , SiR 2 , or BR;
M is Rh(I) or Ir(I);
each R is independently selected from the group consisting o hydrogen, halogen, or substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl; and
each Ar 1 is substituted or unsubstituted aryl or heteroaryl.

4. The complex of claim 1 , wherein the complex is represented by one of the following structures:

wherein:
U is O, S, NR, PR, AsR, CR 2 , SiR 2 , or BR,
M is Au(III);
each R is independently hydrogen, halogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, or aryl; and
each Ar 1 is independently substituted or unsubstituted aryl or heteroaryl.

5. A light emitting device comprising the complex of claim 1 .

6. An OLED device comprising the complex of claim 1 .

7. The OLED device of claim 6 , wherein the device is a phosphorescent OLED device.

8. A photovoltaic device comprising the complex of claim 1 .

9. A luminescent display device comprising the complex of claim 1 .

Assignees

• Univ Arizona State
• Arizon Board Of Regents On Behalf Of Arizona State Univ

Inventors

• Li Jian
• Zhu zhi-qiang

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title