US5948552A — Heat-resistant organic electroluminescent device

Claim 1

Independent Claim 163 words

An organic electroluminescent device, comprising: a substrate; a first conductive layer on the substrate, the first conductive layer being translucent; an electron-transporting and light-emitting layer; a second conductive layer adjacent the electron-transporting and light-emitting layer and remote from the first conductive layer, and a hole transporting layer sandwiched between the first conductive layer and the electron-transporting and light-emitting layer, the hole-transporting layer comprising a poly(arylamine) including at least one compound of formula (I): ##STR9## in which: R is independently in each occurrence a C 1-24 hydrocarbyl, hydrocarboxyl, hydrothiocarboxy, hydroarylcarboxy, or hydrothioarylcarboxy; Ar 1 and Ar 2 are independently in each occurrence a C 6-18 aryl moiety optionally substituted with one or more C 1-24 hydroaryl, hydrocarboxyl, hydrothiocarboxy, hydroarylcarboxy, or hydrothioarylcarboxy; A is independently in each occurrence hydrogen or a halogen; x is independently in each occurrence a positive number between 0 and 1; n is a whole number from 0 to 4; and m is a number from about 5 to about 1000.

Claim 2

Dependent Claim 163 words

An organic electroluminescent device, comprising: a substrate; a first conductive layer on the substrate, the first conductive layer being translucent; an electron-transporting and light-emitting layer; a second conductive layer adjacent the electron-transporting and light-emitting layer and remote from the first conductive layer, and a hole transporting layer sandwiched between the first conductive layer and the electron-transporting and light-emitting layer, the hole-transporting layer comprising a poly(arylamine) including at least one compound of formula (I): ##STR9## in which: R is independently in each occurrence a C 1-24 hydrocarbyl, hydrocarboxyl, hydrothiocarboxy, hydroarylcarboxy, or hydrothioarylcarboxy; Ar 1 and Ar 2 are independently in each occurrence a C 6-18 aryl moiety optionally substituted with one or more C 1-24 hydroaryl, hydrocarboxyl, hydrothiocarboxy, hydroarylcarboxy, or hydrothioarylcarboxy; A is independently in each occurrence hydrogen or a halogen; x is independently in each occurrence a positive number between 0 and 1; n is a whole number from 0 to 4; and m is a number from about 5 to about 1000.

Claim 3

Dependent Claim 71 words

The organic electroluminescent device of claim 1, in which the electron transporting and light-emitting layer includes a metal chelated oxinoid compound represented by the structural formula (0): ##STR10## in which Me represents a metal, q is an integer between 0 and 3 and X independently in each occurrence represents atoms completing a nucleus having at least two fused aromatic rings, at least one of which is an azole or azine ring.

Claim 4

Dependent Claim 18 words

The organic electroluminescent device of claim 2, in which the electron transporting and light-emitting layer includes aluminum tris-8-hydroxyquinoline.

Claim 5

Dependent Claim 18 words

The organic electroluminescent device of claim 2, in which the electron-transporting and light-emitting layer includes a fluorescent dye.

Claim 6

Dependent Claim 24 words

The organic electroluminescent device of claim 1, in which the second conductive layer includes a metal having work function of less than 5 eV.

Claim 7

Dependent Claim 67 words

The organic electroluminescent device of claim 1, additionally comprising a layer of an aromatic tertiary amine interposed between the layer of the poly(arylamine) and the electron-transporting and light-emitting layer, the aromatic tertiary amine containing at least two tertiary amine molecules and including, attached to a tertiary amine nitrogen atom, an aromatic moiety containing one of (a) an aromatic ring and (b) at least two fused aromatic rings.

Claim 8

Dependent Claim 17 words

The organic electroluminescent device of claim 6, in which the aromatic tertiary amine includes N,N'-diphenyl-N-N'-bis(3-methylphenyl)- 1, 1'-biphenyl-4,4'-diamine.

Claim 9

Dependent Claim 18 words

The organic electroluminescent device of claim 1, in which the electron-transporting and light-emitting layer comprises a light-emitting polymer.

Claim 10

Dependent Claim 23 words

The organic electroluminescent device of claim 1 or 2, in which x=1, n=0, Ar 1 =1,4-phenylene, Ar 2 =phenyl, and m=5 to 1000.

Claim 11

Dependent Claim 23 words

The organic electroluminescent device of claim 1 or 2, in which x=1, n=0, Ar 1 =1,3-phenylene, Ar 2 =phenyl, and m=5 to 1000.

Claim 12

Dependent Claim 23 words

The organic electroluminescent device of claim 1 or 2, in which x=1, n=0, Ar 1 =1,4-phenylene, Ar 2 =4-methoxyphenyl, and m=5 to 1000.

Claim 13

Dependent Claim 97 words

The organic electroluminescent device of claim 1, in which: R is independently in each occurrence a C 1 to C 12 hydrocarbyl, alkoxyl, thioalkoxy, aryloxy, or thioaryloxy moiety optionally substituted with C 1 to C 12 alkoxyl, thioalkoxy, aryloxy, or thioaryloxy moieties; Ar 1 and Ar 2 are independently in each occurrence a C 6 to C 12 aromatic compound optionally substituted with C 1 to C 12 hydrocarbyl, alkoxyl, thioalkoxy, aryloxy, or thioaryloxy moieties; A is independently in each occurrence hydrogen, chlorine, or bromine; and m is a number of from about 5 to about 500.

Claim 14

Dependent Claim 93 words

The organic electroluminescent device of claim 1, in which: R is independently in each occurrence a C 1 to C 5 alkoxy, thioalkoxy or a C 1 to C 6 hydrocarbyl; Ar 1 and Ar 2 are independently in each occurrence a phenyl, naphthyl or biphenyl, optionally substituted with C 1 to C 5 alkoxy or C 1 to C 6 hydrocarbyl; A is independently in each occurrence hydrogen, chlorine or bromine; n is a number of from 0 to 1; and m is a number of from about 5 to about 100.

Claim 15

Dependent Claim 57 words

The organic electroluminescent device of claim 1, in which: R is independently in each occurrence methyl or methoxy; Ar 1 and Ar 2 are independently in each occurrence anisole, methoxynapthalene, methoxybiphenyl, or phenyl or toluene; A is independently in each occurrence hydrogen, chlorine or bromine; and m is a number of from about 5 to about 100.

Claim 16

Dependent Claim 55 words

The organic electroluminescent device of claim 1, in which: Ar 1 is independently in each occurrence benzyl; Ar 2 is independently in each occurrence methoxyphenyl or phenyl; A is independently in each occurrence hydrogen, chlorine or bromine; n is a number of 0; and m is a number of from about 5 to about 100.

Claim 17

Independent Claim 193 words

A method of making an organic electroluminescent device, the method comprising steps of: providing: a substrate having a translucent conductive layer, a solution of a poly(arylamine) including at least one compound of formula (I): ##STR11## in which: R is independently in each occurrence a C 1-24 hydrocarbyl, hydrocarboxyl, hydrothiocarboxy, hydroarylcarboxy, or hydrothioarylcarboxy; Ar 1 and Ar 2 are independently in each occurrence a C 6-18 aryl moiety optionally substituted with one or more C 1-24 hydrocarbyl, hydrocarboxyl, hydrothiocarboxy, hydroarylcarboxy, or hydrothioarylcarboxy; A is independently in each occurrence hydrogen or a halogen; x is independently in each occurrence a positive number between 0 and 1 inclusive; n is a whole number from 0 to 4; and m is a number from about 5 to about 1000, an electron-transporting and light-emitting material, and a conductive material; and forming a device structure on the translucent conductive layer by steps including: coating from the solution a layer of the poly(arylamine) onto the translucent conductive layer, depositing a layer of the electron-transporting and light-emitting material on the layer of the poly(arylamine), and depositing a layer of the conductive material on the layer of the electron-transporting and light-emitting material.

Claim 18

Independent Claim 193 words

A method of making an organic electroluminescent device, the method comprising steps of: providing: a substrate having a translucent conductive layer, a solution of a poly(arylamine) including at least one compound of formula (I): ##STR11## in which: R is independently in each occurrence a C 1-24 hydrocarbyl, hydrocarboxyl, hydrothiocarboxy, hydroarylcarboxy, or hydrothioarylcarboxy; Ar 1 and Ar 2 are independently in each occurrence a C 6-18 aryl moiety optionally substituted with one or more C 1-24 hydrocarbyl, hydrocarboxyl, hydrothiocarboxy, hydroarylcarboxy, or hydrothioarylcarboxy; A is independently in each occurrence hydrogen or a halogen; x is independently in each occurrence a positive number between 0 and 1 inclusive; n is a whole number from 0 to 4; and m is a number from about 5 to about 1000, an electron-transporting and light-emitting material, and a conductive material; and forming a device structure on the translucent conductive layer by steps including: coating from the solution a layer of the poly(arylamine) onto the translucent conductive layer, depositing a layer of the electron-transporting and light-emitting material on the layer of the poly(arylamine), and depositing a layer of the conductive material on the layer of the electron-transporting and light-emitting material.

Claim 19

Dependent Claim 119 words

The method of claim 16, in which: in the providing step, an aromatic tertiary amine is additionally provided, the aromatic tertiary amine containing at least two tertiary amine molecules and including, attached to a tertiary amine nitrogen atom, an aromatic moiety containing one of (a) an aromatic ring and (b) at least two fused aromatic rings; the step of forming a device structure additionally includes a step of depositing a layer of the aromatic tertiary amine onto the layer of the poly(arylamine) to form a hole-transporting layer; and in the step of depositing a layer of the electron-transporting and light-emitting material, the layer of the electron-transporting and light-emitting material is deposited on the layer of the aromatic tertiary amine.

Claim 20

Dependent Claim 18 words

The method of claim 17, in which the aromatic tertiary amine is deposited by vapor deposition in vacuum.

Claim 21

Dependent Claim 22 words

The method of claim 17, in which, in the step of providing an aromatic tertiary amine, the aromatic tertiary amine includes N,N'-diphenyl-N-N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine.

Claim 22

Dependent Claim 14 words

The method of claim 16, additionally comprising a step of post-annealing the device structure.

Claim 23

Dependent Claim 46 words

The method of claim 16, in which the step of forming a device structure on the conductive layer additionally includes a step of annealing the substrate and the layer of the poly(arylamine) prior to the step of depositing the layer of the electron-transporting and light-emitting material.

Claim 24

Dependent Claim 74 words

The method of claim 16, in which, in the step of providing an electron-transporting and light-emitting material, a metal chelated oxinoid compound represented by the structural formula (0) is provided: ##STR12## in which Me represents a metal, q is an integer between 0 and 3 and X independently in each occurrence represents atoms completing a nucleus having at least two fused aromatic rings, at least one of which is an azole or azine ring.

Claim 25

Dependent Claim 15 words

The method of claim 22, in which the metal chelated oxinoid compound includes aluminum tris-8-hydroxyquinoline.

Claim 26

Dependent Claim 45 words

The method of claim 16, in which: the method additionally comprises a step of providing a fluorescent dye; and the step of depositing the layer of the electron-transporting and light-emitting material includes a step of doping the electron-transporting and light-emitting material with the fluorescent dye.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	2002-09-06	2003-03-08	2003-09-07	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2006-09-06	2007-03-08	2007-09-07	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2010-09-06	2011-03-08	2011-09-07	$7700.00	Window Closed / Lapsed

Heat-resistant organic electroluminescent device

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