Electroluminescent device with organic luminescent medium

• US 4,720,432 A
• Filed: 02/11/1987
• Issued: 01/19/1988
• Est. Priority Date: 02/11/1987
• Status: Expired due to Term

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Tang, Ching W., Roberts, Luther C., VanSlyke, Steven A.
• Primary Examiner(s): Robinson, Ellis P.
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US07/013,528
• Time in Patent Office: 342 Days
• Field of Search: 428/917, 428/515, 428/461, 428/411.1, 428/457, 313/498, 313/504, 313/506, 313/509, 252/301.16, 357/8
• US Class Current: 428/457
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: Y10S 428/917 Electroluminescent
• CPC Class Codes: Y10T 428/31504 Composite [nonstructural laminate]
• CPC Class Codes: Y10T 428/31678 Of metal
• CPC Class Codes: Y10T 428/31692 Next to addition polymer from unsaturated monomers
• CPC Class Codes: Y10T 428/31909 Next to second addition polymer from unsaturated monomers

Abstract

An electroluminescent device is disclosed comprising in sequence, an anode, an organic hole injecting and transporting zone, an organic electron injecting and transporting zone, and a cathode. The organic hole injecting and transporting zone is comprised of a layer in contact with the anode containing a hole injecting porphyrinic compound and a layer containing a hole transporting aromatic tertiary amine interposed between the hole injecting layer and the electron injecting and transporting zone.

Claims

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

said organic hole injecting and transporting zone is comprised of

a layer in contact with said anode containing a hole injecting porphyrinic compound and

a layer containing a hole transporting aromatic tertiary amine interposed between said hole injecting layer and said electron injecting and transporting zone.

2. An electroluminescent device according to claim 1 in which said cathode contains a metal having a work function of less than 4 eV other than an alkali metal and is light transmissive.

3. An electroluminescent device according to claim 1 in which said hole transporting layer is comprised of

a tetraphenyldiamine layer contacting said electron injecting and transporting zone and

a triarylamine layer contacting said hole injecting layer.

4. An electroluminescent device according to claim 1 in which said aromatic tertiary amine is a diphenylamine.

5. An electroluminescent device according to claim 4 in which said diphenylamine is a carbazole.

6. An electroluminescent device according to claim 1 in which said aromatic tertiary amine is a triphenylamine.

7. An electroluminescent device according to claim 6 in which said triphenylamine is N,N,N-triphenylamine.

8. An electroluminescent device according to claim 1 in which said aromatic tertiary amine satisfies the structural formula:

##STR10## wherein Q¹ and Q² are independently aromatic tertiary amine moieties and

G is a linking group chosen from the class consisting of phenylene, cycloalkylene having 5 to 7 ring carbon atoms, or alkylene having from 1 to 6 carbon atoms, or a carbon to carbon bond.

9. An electroluminescent device according to claim 8 in which said aromatic tertiary amine is a triphenylamine satisfying the structural formula:

##STR11## where R¹ and R² each independently represents a hydrogen atom, a phenyl group, or an alkyl group of from 1 to 6 carbon atoms or R¹ and R² together represent the atoms completing a cycloalkyl group containing from 5 to 7 ring carbon atoms and

R³ and R⁴ each independently represents a phenyl group which is in turn substituted with a diphenylamino group, as indicated by the structural formula;

##STR12## wherein R⁵ and R⁶ are independently selected phenyl groups.

10. An electroluminescent device according to claim 1 in which said aromatic tertiary amine is a tetraphenyldiamine.

11. An electroluminescent device according to claim 10 in which said tetraphenyldiamine satisfies the formula:

R1 ? ? ##STR13## wherein Are is a phenylene group,

n is an integer of from 1 to 4, and

Ar, R⁷, R⁸, and R⁹ are independently selected phenyl groups.

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

##STR14## wherein Q is --N═

or --C(R)═

;

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

R is hydrogen, alkyl, phenalkyl, phenyl, or alkylphenyl, each alkyl moiety containing from 1 to 6 carbon atoms, 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.

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

##STR15## wherein Q is --N═

or --C(R)═

;

R is hydrogen, alkyl, phenalkyl, phenyl, or alkylphenyl, each alkyl moiety containing from 1 to 6 carbon atoms, 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.

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

15. An electroluminescent device according to claim 14 in which said chelated oxinoid compound is represented by the formula:

##STR16## 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.

16. An electroluminescent device comprising in sequence

an anode,

a hole injecting layer comprised of a porphyrinic compound,

a hole transporting layer comprised of an aromatic tertiary amine,

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.

17. An electroluminescent device according to claim 16 in which said anode is opaque and said cathode is light transmissive.

18. An electroluminescent device according to claim 16 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.

19. An electroluminescent device according to claim 16 in which said cathode includes at least one metal having a work function greater than 4 eV.

20. An electroluminescent device comprising in sequence

an opaque anode,

a hole injecting layer comprised of a phthalocyanine,

a first hole transporting layer comprised of a tetraphenyldiamine,

a second hole transporting layer comprised of a triphenylamine,

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

a light transmissive 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 and being chosen from the group consisting of magnesium, a rare earth metal, or indium, and

at least one other of said metals being chosen from the group consisting of aluminum, copper, silver, gold, tin, lead, bismuth, tellurium, indium, and antimony.