US4539507A — Organic electroluminescent devices having improve…

Claim 1

Independent Claim 178 words

In an electroluminescent device comprising, in sequence, an anode electrode, a hole-injecting zone, an organic luminescent zone, and a cathode electrode, at least one of said electrodes being capable of transmitting at least 80% of radiation having wavelengths longer than 400 nm, the improvement wherein said luminescent zone comprises an electron-transporting compound that provides a maximum electroluminescent quantum efficiency of at least about 5×10 -4 photons/electron, when used in a test device driven at no more than the lesser of (i) 25 volts and (ii) the voltage which produces the maximum power conversion efficiency of said device, said test device comprising (1) a hole-injecting zone consisting essentially of 1,1-bis-(4-di-p-tolylaminophenyl)cyclohexane, said hole-injecting zone and said luminescent zone having a combined thickness of no more than 1 micron, (2) an anode electrode that transmits at least 80% of radiation having wavelengths longer than 400 nm, and (3) an indium cathode, and wherein said device has a power conversion efficiency of at least 9×10 -5 w/w and said zones have a combined thickness that is no greater than about 1 micron.

Claim 2

Dependent Claim 178 words

In an electroluminescent device comprising, in sequence, an anode electrode, a hole-injecting zone, an organic luminescent zone, and a cathode electrode, at least one of said electrodes being capable of transmitting at least 80% of radiation having wavelengths longer than 400 nm, the improvement wherein said luminescent zone comprises an electron-transporting compound that provides a maximum electroluminescent quantum efficiency of at least about 5×10 -4 photons/electron, when used in a test device driven at no more than the lesser of (i) 25 volts and (ii) the voltage which produces the maximum power conversion efficiency of said device, said test device comprising (1) a hole-injecting zone consisting essentially of 1,1-bis-(4-di-p-tolylaminophenyl)cyclohexane, said hole-injecting zone and said luminescent zone having a combined thickness of no more than 1 micron, (2) an anode electrode that transmits at least 80% of radiation having wavelengths longer than 400 nm, and (3) an indium cathode, and wherein said device has a power conversion efficiency of at least 9×10 -5 w/w and said zones have a combined thickness that is no greater than about 1 micron.

Claim 3

Dependent Claim 15 words

A device as defined in claim 1, wherein said electron-transporting compound is an optical brightener.

Claim 4

Dependent Claim 179 words

A device as defined in claim 2, wherein said optical brightener has a structural formula selected from the class consisting of ##STR26## wherein (1) R 1 , R 2 , R 3 and R 4 are individually hydrogen, saturated aliphatic of from 1 to 10 carbon atoms, aryl of from 6 to 10 carbon atoms, or halo, or (2) R 1 and R 2 or R 3 and R 4 taken together comprise the atoms necessary to complete a fused aromatic ring; R 5 is saturated aliphatic of from 1 to 20 carbon atoms, aryl of from 6 to 10 carbon atoms, carboxyl, hydrogen, cyano or halo; provided that in formula (b) at least two of R 3 , R 4 and R 5 are saturated aliphatic of from 3 to 10 carbon atoms; Z is --O--, --NH--, or --S--; Y is ##STR27## m is an integer of from 0 to 4; n is 0, 1, 2 or 3; R 6 is arylene of from 6 to 10 carbon atoms; and Z' and Z" are individually N or CH.

Claim 5

Dependent Claim 27 words

A device as defined in claim 2, wherein said optical brightener is selected from the group consisting of 4,4'-bis(5,7-di-t-pentyl-2-benzoxazolyl)stilbene; 2,5-bis(5,7-di-t-pentyl-2-benzoxazolyl)-1,3,4-thiadiazole; 2,5-bis(5,7-di-t-phenyl-2-benzoxazolyl)thiophene; 2,2'-p-(phenylenedivinylene)bisbenzothiazole; 4,4'-bis(2-benzoxazolyl)biphenyl; 2,5-bis[5-(α,α-dimethylbenzyl)-2-benzoxazolyl]-thiophene; 4,4'-bis[5,7-di-(2-methyl-2-butyl)-2-benzoxazolyl]-stilbene; and 2,5-bis[5,7-di-(2-methyl-2-butyl)-2-benzoxazolyl]-3,4-diphenylthiophene.

Claim 6

Dependent Claim 17 words

A device as defined in claim 1, wherein said electron-transporting compound is a metal complex of 8-hydroxyquinoline.

Claim 7

Dependent Claim 26 words

A device as defined in claim 5, wherein the metal of said metal complex is selected from the group consisting of Zn, Al, Mg and Li.

Claim 8

Dependent Claim 136 words

In an electroluminescent device comprising, in sequence, an anode electrode, a hole-injecting zone, an organic luminescent zone, and a cathode electrode, at least one of said electrodes being capable of transmitting at least 80% of radiation having wavelengths longer than 400 nm, the improvement wherein said hole-injecting zone comprises an amine that transmits at least about 90% of radiation having wavelengths greater than 400 nm, at least one nitrogen atom of the amine being trisubstituted with substituents at least one of which is aryl, said amine being solid at room temperature and having the structural formula ##STR28## wherein Q 1 and Q 2 are individually moieties containing nitrogen and at least 3 carbocyclic rings at least one of which is aromatic, and, G is a linking group or a carbon-to-carbon bond, whereby said amine is thin-film-forming.

Claim 9

Dependent Claim 136 words

In an electroluminescent device comprising, in sequence, an anode electrode, a hole-injecting zone, an organic luminescent zone, and a cathode electrode, at least one of said electrodes being capable of transmitting at least 80% of radiation having wavelengths longer than 400 nm, the improvement wherein said hole-injecting zone comprises an amine that transmits at least about 90% of radiation having wavelengths greater than 400 nm, at least one nitrogen atom of the amine being trisubstituted with substituents at least one of which is aryl, said amine being solid at room temperature and having the structural formula ##STR28## wherein Q 1 and Q 2 are individually moieties containing nitrogen and at least 3 carbocyclic rings at least one of which is aromatic, and, G is a linking group or a carbon-to-carbon bond, whereby said amine is thin-film-forming.

Claim 10

Dependent Claim 62 words

In an electroluminescent device comprising, in sequence, an anode electrode, a hole-injecting zone, an organic luminescent zone, and a cathode electrode, at least one of said electrodes being capable of transmitting at least 80% of radiation having wavelengths longer than 400 nm, the improvement wherein said hole-injecting zone comprises an amine selected from the group consisting of bis(4-dimethylamino-2-methylphenyl)phenylmethane; N,N,N-tri(p-tolyl)amine; 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane; and 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane.

Claim 11

Dependent Claim 62 words

In an electroluminescent device comprising, in sequence, an anode electrode, a hole-injecting zone, an organic luminescent zone, and a cathode electrode, at least one of said electrodes being capable of transmitting at least 80% of radiation having wavelengths longer than 400 nm, the improvement wherein said hole-injecting zone comprises an amine selected from the group consisting of bis(4-dimethylamino-2-methylphenyl)phenylmethane; N,N,N-tri(p-tolyl)amine; 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane; and 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane.

Claim 12

Dependent Claim 69 words

In an electroluminescent device comprising, in sequence, an anode electrode, a hole-injecting zone, an organic luminescent zone, and a cathode electrode, at least one of said electrodes being capable of transmitting at least 80% of radiation having wavelengths longer than 400 nm, the improvement wherein said hole-injecting zone comprises 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane; and said luminescent zone comprises 2,5-bis(5,7-di-t-pentyl-2-benzoxazolyl)-1,3,4-thiadiazole; said two zones having a combined thickness no greater than about 1 micron.

Claim 13

Dependent Claim 69 words

In an electroluminescent device comprising, in sequence, an anode electrode, a hole-injecting zone, an organic luminescent zone, and a cathode electrode, at least one of said electrodes being capable of transmitting at least 80% of radiation having wavelengths longer than 400 nm, the improvement wherein said hole-injecting zone comprises 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane; and said luminescent zone comprises 2,5-bis(5,7-di-t-pentyl-2-benzoxazolyl)-1,3,4-thiadiazole; said two zones having a combined thickness no greater than about 1 micron.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1988-09-02	1989-03-04	1989-09-03	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	1992-09-02	1993-03-04	1993-09-03	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	1996-09-02	1997-03-04	1997-09-03	$7700.00	Window Closed / Lapsed

Organic electroluminescent devices having improved power conversion efficiencies

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