Emissive polymeric materials for optoelectronic devices
View Patent ↗Polymers including at least one structural unit derived from a compound of formula I or including at least one pendant group of formula II may be used in optoelectronic devices wherein R 1 , R 3 , R 4 and R 6 are independently hydrogen, alkyl, alkoxy, oxaalkyl, alkylaryl, aryl, arylalkyl, heteroaryl, substituted alkyl; substituted alkoxy, substituted oxaalkyl, substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted heteroaryl; R 1a is hydrogen or alkyl; R 2 is alkylene, substituted alkylene, oxaalkylene, CO, or CO 2 ; R 2a is alkylene; R 5 is independently at each occurrence hydrogen, alkyl, alkylaryl, aryl, arylalkyl, alkoxy, carboxy, substituted alkyl; substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted alkoxy, X is halo, triflate, —B(OR 1a ) 2 , or located at the 2, 5- or 2, 7-positions; and L is derived from phenylpyridine, tolylpyridine, benzothienylpyridine, phenylisoquinoline, dibenzoquinozaline, fluorenylpyridine, ketopyrrole, 2-(1-naphthyl)benzoxazole)), 2-phenylbenzoxazole, 2-phenylbenzothiazole, coumarin, thienylpyridine, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, phenylimine, vinylpyridine, pyridylnaphthalene, pyridylpyrrole, pyridylimidazole, phenylindole, derivatives thereof or combinations thereof.
1. An optoelectronic device comprising a polymer having at least one pendant group of formula
wherein
R 2 is alkylene, substituted alkylene, oxaalkylene, CO, or CO 2 ;
R 3 , R 4 and R 6 are independently hydrogen, alkyl, alkoxy, alkylaryl, aryl, arylalkyl, heteroaryl, substituted alkyl; substituted alkoxy, substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted heteroaryl;
L is derived from phenylpyridine, tolylpyridine, benzothienylpyridine, phenylisoquinoline, dibenzoquinozaline, fluorenylpyridine, ketopyrrole, 2-(1-naphthyl)benzoxazole)), 2-phenylbenzoxazole, 2-phenylbenzothiazole, coumarin, thienylpyridine, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, phenylimine, vinylpyridine, pyridylnaphthalene, pyridylpyrrole, pyridylimidazole, phenylindole, derivatives thereof or combinations thereof.
2. An optoelectronic device according to claim 1 , wherein the polymer additionally comprises structural units derived from at least one fluorene monomer.
3. An optoelectronic device according to claim 1 , wherein the polymer additionally comprises structural units derived from a dibromo 9,9-dioctyl fluorene monomer.
4. An optoelectronic device according to claim 1 , wherein the polymer additionally comprises structural units derived from at least one triarylamine monomer.
5. An optoelectronic device according to claim 1 , wherein L is derived from phenylisoquinoline.
6. An optoelectronic device according to claim 1 , wherein R 2 is oxaalkylene.
7. An optoelectronic device according to claim 1 , wherein the pendant group is
8. An optoelectronic device according to claim 1 , wherein the pendant group is
wherein piq is phenylisoquinolinyl.
9. An optoelectronic device according to claim 1 , wherein the pendant group is derived from a compound of formula
wherein
R 1 , R 3 , R 4 and R 6 are independently hydrogen, alkyl, alkoxy, oxaalkyl, alkylaryl, aryl, arylalkyl, heteroaryl, substituted alkyl; substituted alkoxy, substituted oxaalkyl, substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted heteroaryl;
R 1a is hydrogen or alkyl;
R 2 is alkylene, substituted alkylene, oxaalkylene, CO, or CO 2 ;
R 2a is alkylene;
R 5 is independently at each occurrence hydrogen, alkyl, alkylaryl, aryl, arylalkyl, alkoxy, carboxy, substituted alkyl; substituted alkylaryl, substituted aryl, substituted arylalkyl, or substituted alkoxy,
X is halo, triflate, —B(OR 1a ) 2 , or
located at the 2, 5- or 2, 7-positions; and
L is derived from phenylpyridine, tolylpyridine, benzothienylpyridine, phenylisoquinoline, dibenzoquinozaline, fluorenylpyridine, ketopyrrole, 2-(1-naphthyl)benzoxazole)), 2-phenylbenzoxazole, 2-phenylbenzothiazole, coumarin, thienylpyridine, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, phenylimine, vinylpyridine, pyridylnaphthalene, pyridylpyrrole, pyridylimidazole, phenylindole, derivatives thereof or combinations thereof.
10. An optoelectronic device according to claim 1 , wherein the pendant group is derived from a compound selected from
wherein Z is O, S, or a direct bond.
11. An optoelectronic device according to claim 1 , comprising structural units of formula
12. An optoelectronic device according to claim 1 , comprising structural units of formula
wherein piq is phenylsoquinolinyl.
13. An optoelectronic device according to claim 1 , comprising structural units of formula
wherein piq is phenylsoquinolinyl.
14. An optoelectronic device according to claim 1 , additionally comprising a fluorescent emitting material.
15. An optoelectronic device according to claim 14 , wherein the fluorescent material is a blue emitting polymer.
16. An optoelectronic device according to claim 14 , where the fluorescent emitting material comprises a polymer having structural units derived from a fluorene monomer.
17. An optoelectronic device according to claim 1 , additionally comprising at least one photoluminescent (“PL”) material optically coupled with the polymer such that the phosphor material absorbs a portion of EM radiation emitted thereby and emits EM radiation in a third wavelength range.