Electroluminescent device with modified thin film luminescent zone

• US 4,769,292 A
• Filed: 10/14/1987
• Issued: 09/06/1988
• Est. Priority Date: 03/02/1987
• Status: Expired due to Term

• Current Assignee: Eastman Kodak Company
• Original Assignee: Eastman Kodak Company
• Inventors: Tang, Ching W., Goswami, Ramanuj, Chen, Chin H.
• Primary Examiner(s): Swisher, Nancy A. B.
• Application Number:
  US07/108,342
• Time in Patent Office: 328 Days
• Field of Search: 428/690, 428/691, 428/917, 313/503
• US Class Current: 428/690
• 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: H05B 33/28 of translucent electrodes
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/311 Phthalocyanine
• CPC Class Codes: H10K 85/621 Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
• CPC Class Codes: H10K 85/631 Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
• CPC Class Codes: H10K 85/652 Cyanine dyes
• CPC Class Codes: Y10S 428/917 Electroluminescent

Abstract

An electroluminescent device is disclosed having a luminescent zone of less than one μm in thickness comprised of an organic host material capable of sustaining hole-electron recombination and a fluorescent material capable of emitting light in response to energy released by hole-electron recombination.

Claims

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

characterized in that

said luminescent zone is formed of a thin film of less than 1 μ

m in thickness comprised of

an organic host material forming a layer capable of sustaining both hole and electron injection and

located in said layer as a fluorescent material a dye capable of emitting light in response to hole-electron recombination, said dye having a bandgap no greater than that of said host material and a reduction potential less negative than that of said host material.

2. An organic electroluminescent device according to claim 1 in which said fluorescent material is chosen to provide favored sites for light emission.

3. An organic electroluminescent device according to claim 1 in which said cathode is comprised of a metal other than an alkali metal having a work function of less than 4 eV.

4. An organic electroluminescent device according to claim 1 in which 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 luminescent zone.

5. An organic electroluminescent device according to claim 1 in which said dye is chosen from the class consisting of coumarin, dicyanomethylenepyrans and thiopyrans, polymethine, oxabenzanthracene, xanthene, pyrylium and thiapyrylium, carbostyril, and perylene fluorescent dyes.

6. An organic electroluminescent device according to claim 5 in which said fluorescent dye is a coumarin dye of the formula:

##STR65## where R¹ is chosen from the group consisting of hydrogen, carboxy, alkanoyl, alkoxycarbonyl, cyano, aryl, and a heterocylic aromatic group,

R² is chosen from the group consisting of hydrogen, alkyl, haloalkyl, carboxy, alkanoyl, and alkoxycarbonyl,

R³ is chosen from the group consisting of hydrogen and alkyl,

R⁴ is an amino group, and

R⁵ is hydrogen, or

R¹ and R² together form a fused carbocyclic ring, or

the amino group forming R⁵ independently completes with at least one of R⁴ and R⁶ a fused ring.

7. An organic electroluminescent device according to claim 5 in which said fluorescent dye is a dye of the formula:

##STR66## where X represents oxygen or sulfur;

R⁶ represents a 2-(4-aminostyryl) group; and

R⁷ represents a second R⁶ group, an alkyl group, or a phenyl group.

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

9. An organic electroluminescent device according to claim 8 in which said cathode is formed of a combination of metals other than alkali metals having a work function of less than 4 eV.

10. An organic electroluminescent device according to claim 8 in which said cathode additionally includes less than 50 atomic percent of a second metal having a work function of greater than 4 eV.

11. An organic electroluminescent device according to claim 1 in which said fluorescent material is present in a concentration of from 10^-3 to 10 mole percent, based on the moles of host material.

12. An organic electroluminescent device comprising in sequence, an anode, an organic luminescent medium, and a cathode,

characterized in that

said organic luminescent medium is less than 5000 Angstroms in thickness and is comprised of

an electron injecting and transporting layer containing

an organic host material capable of sustaining both hole and electron injection and

located in said layer as a fluorescent material a dye chosen to provide favored sites for light emission having a bandgap no greater than that of said host material and a reduction potential less negative than that of said host material.

13. An organic electroluminescent device according to claim 12 in which said host material is capable of emitting light of a first wavelength in the absence of said fluorescent material and said fluorescent material is capable of absorbing light at the first wavelength.

14. An organic electroluminescent device according to claim 13 in which the wavelength of maximum light emitted by said host material in the absence of said fluorescent material is within 25 nm of the wavelength of maximum light absorption by said fluorescent material.

15. An organic electroluminescent device according to claim 12 in which 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 luminescence zone.

16. An organic electroluminescent device according to claim 12 in which said host material is a chelated oxinoid compound.

17. An organic electroluminescent device according to claim 16 in which said chelated oxinoid compound is represented by the structure:

##STR67## wherein Mt represents a metal;

n is an integer of from 1 to 3; and

Z² independently in each occurrence represents the atoms completing a nucleus having at least two fused aromatic rings.

18. An organic electroluminescent device comprising in sequence

an anode formed of one or more metals having a work function of greater than 4 eV,

a cathode formed of a combination of metals, with one or more metals other than alkali metals having a work function of less than 4 eV accounting for greater than 50 percent on an atomic basis of the total cathode metals, and, interposed between said anode and cathode,

an organic luminescent medium consisting of an organic hole injecting zone and a luminescent zone, said organic luminescent medium being less than 5000 Angstroms in thickness and comprised of

an electron injecting and transporting layer containing

an organic host material capable of sustaining both hole and electron injection and

located in said layer as an optically coupled fluorescent material chosen to provide favored sites for light emission a dye having a bandgap no greater than that of said host material and a reduction potential less negative than that of said host material and

a hole injecting and transporting zone comprised of

a tetraphenyldiamine layer contacting said electron injecting and transporting zone,

a hole injecting porphyrinic compound containing layer contacting said anode, and

a triphenylamine layer interposed between said tetraphenyldiamine layer and porphyrinic compound.

19. An organic electroluminescent device comprising in sequence

an anode,

a cathode containing magnesium and a minor amount of another metal chosen from the class consisting of aluminum, copper, silver, gold, tin, lead, bismuth, tellurium, indium, and antimony,

at least one of said anode and said cathode being light transmissive, and, interposed between said anode and said cathode,

an organic luminescent medium consisting of an organic hole injecting zone and a luminescent zone, said organic luminescent medium being less than 5000 Angstroms in thickness and comprised of

a hole injecting layer containing a phthalocyanine in contact with said anode,

a first hole transporting layer containing a bis-triphenylamine,

a second hole transporting layer containing a tetraphenyldiamine, and

a luminescent zone containing a metal chelated 8-hydroxyquinoline host material and a fluorescent dye capable of absorbing light at the emission wavelength of said metal chelated 8-hydroxyquinoline, having a lower bandgap and a less negative reduction potential than said chelated 8-hydroxyquinoline.