IP Library Granted Patent US 7,830,081
Granted Patent B2
US 7,830,081 · App. 11/748,195 · Granted Nov 9, 2010

Optoelectronic devices with multilayered structures

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Quick Facts
Patent No.
US 7,830,081
App. No.
11/748,195
Granted
Nov 9, 2010
Kind
B2
Abstract

Optoelectronic devices include polysiloxanes derived from hydrosilation of an organometallic compound of formula L 2 MZ, wherein L and Z are independently bidentate ligands; at least one of L and Z comprises alkenyl, alkenylaryl, alkenyloxy, alkenyloxyaryl, alkynyl, alkynylaryl, alkynyloxy, alkynyloxyaryl, substituted alkenyl, substituted alkenylaryl, substituted alkenyloxy, substituted alkenyloxyaryl, substituted alkynyl, substituted alkynylaryl, substituted alkynyloxy, substituted alkynyloxyaryl, acrylate, methacrylate, or a combination thereof; and M is Zr, Nb, Mo, Tc, Ru, Rh, Pd, Ag, Cd, Hf, Ta, W, Re, Os, Ir, Pt, Au, Hg, Ga, Ge, In, Sn, Sb, Tl, Pd, Bi, Po, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, or Lu.

Claims (33)

1. A polysiloxane derived from hydrosilation of a organometallic compound of formula L 2 MZ,

wherein

L and Z are independently bidentate ligands;

at least one of L and Z comprises alkenyl, alkenylaryl, alkenyloxy, alkenyloxyaryl, alkynyl, alkynylaryl, alkynyloxy, alkynyloxyaryl, substituted alkenyl, substituted alkenylaryl, substituted alkenyloxy, substituted alkenyloxyaryl, substituted alkynyl, substituted alkynylaryl, substituted alkynyloxy, substituted alkynyloxyaryl, acrylate, methacrylate, or a combination thereof; and

M is Ir.

2. A polysiloxane according to claim 1 , wherein L is a cyclometallated ligand.

3. A polysiloxane according to claim 1 , wherein L and Z are independently derived from phenylpyridine, tolylpyridine, benzothienylpyridine, phenylisoquinoline, dibenzoquinozaline, fluorenylpyridine, ketopyrrole, picolinate, acetylacetonate hexafluoroacetylacetonate, salicylidene, 8-hydroxyquinolinate, salicylaldehyde, iminoacetonate, 2-(1 -naphthyl)benzoxazole)), 2-phenylbenzoxazole, 2-phenylbenzothiazole, coumarin, thienylpyridine, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, phenylimine, pyridylnaphthalene, pyridylpyrrole, pyridylimidazole, phenylindole, derivatives thereof or combinations thereof.

4. A polysiloxane according to claim 1 , wherein L is derived from 1-phenylisoquinoline, 2-phenylpyridine, a derivative thereof, or a combination thereof.

5. A polysiloxane according to claim 1 , wherein L is derived from 2-phenylpyridine.

6. A polysiloxane according to claim 1 , wherein Z is derived from ketopyrrole or substituted ketopyrrole, comprising at least one substitutent selected from alkenyl, alkenylaryl, alkenyloxy, alkenyloxyaryl, alkynyl, alkynylaryl, alkynyloxy, alkynyloxyaryl, substituted alkenyl, substituted alkenylaryl, substituted alkenyloxy, substituted alkenyloxyaryl, substituted alkynyl, substituted alkynylaryl, substituted alkynyloxy, substituted alkynyloxyaryl, acrylate, methacrylate, and combinations thereof.

7. A polysiloxane according to claim 6 , wherein Z is derived from a ketopyrrole.

8. A polysiloxane according to claim 7 , wherein Z is derived from a substituted 2-benzoylpyrrole.

9. A polysiloxane derived from hydrosilation of a organometallic compound of the formula

wherein

R 11 and R 12 taken together form a substituted or unsubstituted monocyclic or bicyclic heteroaromatic ring;

R 13 is independently at each occurrence halo, nitro, hydroxy, amino, alkyl, aryl, arylalkyl, alkoxy, substituted alkoxy, substituted alkyl, substituted aryl, or substituted arylalkyl;

R 10 is independently at each occurrence alkenyl, alkenylaryl, alkenyloxy, alkenyloxyaryl, alkynyl, alkynylaryl, al kynyloxy, alkynyloxyaryl, substituted alkenyl, substituted alkenylaryl, substituted alkenyloxy, substituted alkenyloxyaryl, substituted alkynyl, substituted alkynylaryl, substituted alkynyloxy, substituted alkynyloxyaryl, acrylate, methacrylate, or a combination thereof;

X is selected from a direct bond, O, S, alkyl, aryl, alkylaryl, alkoxy, oxaalkyl, substituted alkyl, substituted aryl, substituted alkylaryl, substituted alkoxy, substituted oxaalkyl, and combinations thereof

p is 0, 1 or 2; and

q is 1 or 2.

10. A polysiloxane according to claim 9 , wherein R 10 is allyloxy.

11. A polysiloxane derived from hydrosilation of a organometallic compound of the formula

12. A polysiloxane derived from hydrosilation of a organometallic compound of the formula L 2 MZ and a polyfluorene comprising structural units of formula

wherein

L and Z are independently bidentate ligands;

at least one of L and Z comprises alkenyl, alkenylaryl, alkenyloxy, alkenyloxyaryl, alkynyl, alkynylaryl, alkynyloxy, alkynyloxyaryl, substituted alkenyl, substituted alkenylaryl, substituted alkenyloxy, substituted alkenyloxyaryl, substituted alkynyl, substituted alkynylaryl, substituted alkynyloxy, substituted alkynyloxyaryl, acrylate, methacrylate, or a combination thereof;

M is Zr, Nb, Mo, Tc, Ru, Rh, Pd, Ag, Cd, Hf, Ta, W, Re, Os, Ir, Pt, Au, Hg, Ga, Ge, In, Sn, Sb, TI, Pd, Bi, Po, La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, or Lu; and

R 1 and R 2 are independently alkyl, substituted alkyl, alkenyl, alkenylaryl, alkenyloxy, alkenyloxyaryl, alkynyl, alkynylaryl, alkynyloxy, alkynyloxyaryl, substituted alkenyl, substituted alkenylaryl, substituted alkenyloxy, substituted alkenyloxyaryl, substituted alkynyl, substituted alkynylaryl, substituted alkynyloxy, substituted alkynyloxyaryl, acrylate, methacrylate, or a combination thereof; and at least one of R 1 and R 2 is other than alkyl or substituted alkyl.

13. An organic optoeletronic device comprising a polysiloxane derived from hydrosilation of a organometallic compound of the formula L 2 MZ,

wherein

L and Z are independently bidentate ligands;

at least one of L and Z comprises alkenyl, alkenylaryl, alkenyloxy, alkenyloxyaryl, alkynyl, alkynylaryl, alkynyloxy, alkynyloxyaryl, substituted alkenyl, substituted alkenylaryl, substituted alkenyloxy, substituted alkenyloxyaryl, substituted alkynyl, substituted alkynylaryl, substituted alkynyloxy, substituted alkynyloxyaryl, acrylate, methacrylate, or a combination thereof; and

M is Ir.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2016
From: GENERAL ELECTRIC COMPANY
To: BOE TECHNOLOGY GROUP CO., LTD.
Reel/Frame 038490/0022 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2016
From: GENERAL ELECTRIC COMPANY
To: BOE TECHNOLOGY GROUP CO., LTD.
Reel/Frame 038439/0315 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 14, 2007
From: LEWIS, LARRY NEIL; CHICHAK, KELLY SCOTT; CELLA, JAMES ANTHONY; SHIANG, JOSEPH JOHN
To: GENERAL ELECTRIC COMPANY
Reel/Frame 019289/0887 →