Electroluminescent device with silazane-containing luminescent zone

• US 4,950,950 A
• Filed: 05/18/1989
• Issued: 08/21/1990
• Est. Priority Date: 05/18/1989
• Status: Expired due to Term

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Perry, Robert J., Tang, Ching W.
• Primary Examiner(s): WIEDER, KENNETH A
• Application Number:
  US07/353,832
• Time in Patent Office: 460 Days
• Field of Search: 313/503, 313/504, 313/506, 428/690, 428/691, 428/917
• US Class Current: 313/504
• CPC Class Codes: H05B 33/145 Arrangements of the electroluminescent material
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An electroluminescent device having a luminescent zone of less than one millimicron (μm) in thickness comprised of an organic host material capable of sustaining hole-electron recombination. The hole-transporting agent is a silazane.

Claims

1. An electroluminescent device comprising in sequence, an anode, an organic hole injecting and transporting zone, an electron injecting and transporting zone, and a cathode;

characterized in that said organic hole injecting and transporting zone is comprised of (a) a layer in contact with said anode containing a hole injecting porphyrinic compound and (b) a layer containing a hole transporting silazane, interposed between said hole injecting layer and said electron injecting and transporting zone.

2. An electroluminescent device according to claim 1 wherein said silazane is oxidizable with an oxidation potential within the range of from about 0.5 to about 1.2 electron volts.

3. An electroluminescent device in accordance with claim 2 in which said silazane is a cyclodisilazane.

4. An electroluminescent device in accordance with claim 3 wherein said cyclodisilazane has aryl groups bonded to the nitrogen atoms in the cyclodisilazane ring, such that an aromatic ring in said aryl groups and bonded to said nitrogen atoms, is at least substantially coplanar with said cyclodisilazane ring.

5. An electroluminescent device in accordance with claim 4 wherein said cyclodisilazane has from about 4 to about 8 aromatic rings per molecule.

6. An electroluminescent device of claim 4 in which said cyclodisilazane has a 4-diphenylyl group bonded to each nitrogen atom on the cyclodisilazane ring.

7. An electroluminescent device according to claim 4 wherein each silicon atom in said cyclodisilazane is bonded to an alkyl or aromatic group having up to about 14 carbon atoms.

8. An electroluminescent device in accordance with claim 7 wherein said groups bonded to silicon are selected from methyl and phenyl radicals.

9. An electroluminescent device of claim 8 wherein the nitrogen atoms in said cyclodisilazane ring are bonded to 4-diphenylamino radicals.

10. An electroluminescent device according to claim 1 in which said porphorinic compound is a metal containing porphorinic compound which satisfies the structural formula:

##STR16## wherein;

Q is --N═

or --C(R)═

;

M is a metal, metal oxide, or metal halide;

R is hydrogen, alkyl, aralkyl, aryl, or alkaryl, and

T¹ and T² represent hydrogen or together complete a unsaturated 6 membered ring, containing ring atoms chosen from the group consisting of carbon, nitrogen, and sulfur atoms.

11. An electroluminescent device according to claim 1 in which said porphorinic compound is a metal free porphorinic compound which satisfies the structural formula:

##STR17## wherein;

Q is --N═

or --C(R)═

;

M is a metal, metal oxide, or metal halide;

R is hydrogen, alkyl, aralkyl, aryl, or alkaryl, and

T¹ and T² represent hydrogen or together complete a unsaturated 6 membered ring, containing ring atoms chosen from the group consisting of carbon, nitrogen, and sulfur atoms.

12. An electroluminescent device according to claim 1 in which said electron injecting and transporting zone is comprised of a stilbene or chelated oxinoid compound.

13. An electroluminescent device according to claim 12 in which said chelated oxinoid compound is represented by the formula:

##STR18## wherein;

Me represents a metal;

n is an integer of from 1 to 3; and

Z independently in each occurrence represents the atoms completing a nucleus having at least two fused aromatic rings.

18. An electroluminescent device according to claim 1, wherein said silazane is a polymeric material having a plurality of repeating units having the formula:

##STR19## said units being linked together by Si₂ N₂ bridges having the formula;

##STR20## wherein;

each R is independently selected from the class consisting of hydrogen, lower alkyl groups having from 1 to about 6 carbon atoms, lower alkoxy group having from 1 to about 6 carbon atoms, substituted or unsubstituted vinyl groups, substituted or unsubstituted lower aryl groups having from 6 to about 10 carbon atoms, tri(lower)alkyl and di(lower)alkylsilyl groups and di(lower)alkylamino groups; and

n is an integer greater than 1;

said units being cyclic, linear or branched.

19. An electroluminescent device according to claim 1 wherein said silazane has the formula:

##STR21## wherein each Ar is an aryl radical having from 6 to about 14 carbon atoms, x is a whole number selected from 0 and 1, and R, R¹, and R² are alkyl or aryl radicals having up to about 14 carbon atoms, preferably Ar is a phenyl radical, each x is equal to 1, each R is a phenyl radical, and R¹ and R² are selected from methyl and phenyl radicals.

14. An electroluminescent device comprising in sequence.

an anode,

a hole injecting layer comprised of a porphyrinic compound,

a hole transporting layer comprised of an cyclodisilazane,

an electron injecting and transporting layer comprised of a chelated oxinoid compound, and

a cathode comprised of a layer consisting essentially of a plurality of metals other than alkali metals, at least one of said metals having work function greater than 4 eV.

15. An electroluminescent device according to claim 14 in which said anode is opaque and said cathode is light transmissive.

16. An electroluminescent device according to claim 14 in which said metal having a work function of less than 4 eV includes at least one alkaline earth metal, rare earth metal, or Group III metal.

17. An electroluminescent device according to claim 14 in which said cathode includes at least one metal having a work function greater than 4 eV.

20. Cyclodisilazane having the formula:

##STR22## wherein each Ar is an aryl radical having from 6 to about 14 carbon atoms, x is a whole number selected from 0 and 1, and R, R¹, and R² are alkyl or aryl radicals having up to about 14 carbon atoms, preferably Ar is a phenyl radical, each x is equal to 1, each R is a phenyl radical, and R¹ and R² are selected from methyl and phenyl radicals.