# US 10,483,467 B2 · Organic light emitting diode

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- Number: US 10,483,467 B2
- Document ID: US10483467B2
- Status: Granted
- Kind: B2
- Application number: 15/094,099
- Filed: 2016-04-08
- Published: 2016-10-20
- Granted: 2019-11-19
- Earliest claimed: 2015-04-20
- Assignees: Sfc Co., Ltd.
- Applicants: Sfc Co., Ltd.
- Inventors: Young-hwan Park; Seo-Yeon Yoon; Jeong-Soo Kim; Yeon-Kwon Ryu; Jea-Geon Lim; Ji-Hwan Kim
- Web page: https://patentgrep.com/patent/US10483467B2

## CPC

- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C09K 11/025: {non-luminescent particle coatings or suspension media}
- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1088: containing oxygen as the only heteroatom
- H10K 50/166: {comprising a multilayered structure}
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Disclosed herein is an organic light-emitting diode, comprising an anode, a hole transport layer, a light-emitting layer including a host and a dopant, an electron transport layer, and a cathode in that order, wherein an electron-density-controlling layer including an anthracene derivative represented by the following Chemical Formula A is disposed between the light-emitting layer and the electron transport layer, and wherein an affinity Ah (eV) of the host of the light-emitting layer, an affinity Aed (eV) of the electron-density-controlling layer, and an affinity Ae (eV) of the electron transport layer satisfy an relationship of Ah≥Aed≥Ae.

## Claims

### Claim 1

An organic light-emitting diode, comprising an anode, a hole transport layer, a light-emitting layer including a host and a dopant, an electron transport layer, and a cathode in that order,
wherein an electron-density-controlling layer including an anthracene derivative represented by the following Chemical Formula A-1 or Chemical Formula A-2 is disposed between the light-emitting layer and the electron transport layer, wherein the electron-density-controlling layer is materially different from the electron transport layer,
wherein an affinity Ah (eV) of the host of the light-emitting layer, an affinity Aed (eV) of the electron-density-controlling layer, and an affinity Ae (eV) of the electron transport layer satisfy a relationship of |Ah|≥|Aed|≥|Ae|, and
wherein an electron mobility of the anthracene derivative of the electron-density-controlling layer is not less than that of the material of the electron transport layer:
wherein,
R1 to R8 may be the same or different, and are each independently any one selected from among a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryl thioxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkyl amine of 1 to 30 carbon atoms, a substituted or unsubstituted aryl amine of 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 6 to 30 carbon atoms, a substituted or unsubstituted alkyl germanium of 1 to 30 carbon atoms, a substituted or unsubstituted aryl germanium of 6 to 30 carbon atoms, a cyano, a nitro, and a halogen,
R is an unsubstituted aryl of 6 to 20 carbon atoms,
when there are no R's on the naphthyl ring of Chemical Formula A-1 or the phenyl ring of Chemical Formula A-2, each of the carbon atoms of the aromatic ring moieties has a hydrogen,
n is an integer of 1 to 7, and when n is 2 or greater, R's may be the same or different, and
Ar1 is a heteroaryl of 2 to 20 carbon atoms or an aryl of 6 to 20,
wherein the term ‘substituted’ in the expression ‘substituted or unsubstituted’ means having at least one substituent selected from the group consisting of a deuterium atom, a cyano, a halogen, a hydroxy, a nitro, an alkyl of 1 to 24 carbon atoms, a halogenated alkyl of 1 to 24 carbon atoms, an alkenyl of 2 to 24 carbon atoms, an alkynyl of 2 to 24 carbon atoms, a heteroalkyl of 1 to 24 carbon atoms, an aryl of 6 to 24 carbon atoms, an arylalkyl of 7 to 24 carbon atoms, a heteroaryl of 2 to 24 carbon atoms or a heteroarylalkyl of 2 to 24 carbon atoms, an alkoxy of 1 to 24 carbon atoms, an alkylamino of 1 to 24 carbon atoms, an arylamino of 6 to 24 carbon atoms, a hetero arylamino of 2 to 24 carbon atoms, an alkylsilyl of 1 to 24 carbon atoms, an arylsilyl of 6 to 24 carbon atoms, and an aryloxy of 6 to 24 carbon atoms.

### Claim 2 (depends on 1)

The organic light-emitting diode of claim 1, wherein a difference in triplet energy between the host of the light-emitting layer (ETh (eV)) and the anthracene derivative of the electron-density-controlling layer (ETed (eV)) ranges from 0 to 0.4 (0.4 eV≥ETh−ETed≥0 eV).

### Claim 3 (depends on 1)

The organic light-emitting diode of claim 1, wherein a difference in triplet energy between the host of the light-emitting layer (ETh (eV)) and the anthracene derivative of the electron-density-controlling layer (ETed (eV)) ranges from 0 to 0.3 (0.3 eV≥ETh−ETed≥0 eV).

### Claim 4 (depends on 1)

The organic light-emitting diode of claim 1, wherein the anthracene derivative represented by Chemical Formula A is one selected from among the following Compounds 1, 2, and 7:

### Claim 5 (depends on 1)

The organic light-emitting diode of claim 1, wherein a hole injection layer is introduced between the anode and the hole transport layer, and an electron injection layer is disposed between the electron transport layer and the cathode.

### Claim 6 (depends on 1)

The organic light-emitting diode of claim 1, wherein the host includes at least one of the compounds represented by the following Chemical Formula 1A:
wherein,
X1 to X10 may be the same or different and are each independently selected from the group consisting of a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryl thioxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkyl amine of 1 to 30 carbon atoms, a substituted or unsubstituted aryl amine of 6 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl of 3 to 50 carbon atoms containing at least one heteroatom selected from among O, N, and S, a substituted or unsubstituted silicone, a substituted or unsubstituted boron, a substituted or unsubstituted silane, a carbonyl, a phosphoryl, an amino, a nitrile, a hydroxy, a nitro, a halogen, an amide, and an ester wherein adjacent moieties of X1 to X10 may form a fused, aliphatic, aromatic, heteroaliphatic or heteroaromatic ring.

### Claim 7 (depends on 1)

The organic light-emitting diode of claim 1, wherein the dopant includes at least one selected from among compounds represented by the following Chemical Formulas 2 to 4:
wherein,
A of Chemical Formula 2 is selected from the group consisting of a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl of 3 to 50 carbon atoms containing at least one heteroatom selected from among O, N and S, a substituted or unsubstituted arylene of 6 to 60 carbon atoms, and a substituted or unsubstituted heteroarylene of 3 to 50 carbon atoms containing at least one heteroatom selected from among O, N and S;
X1 and X2, which may the same or different, are each independently selected from among a substituted or unsubstituted arylene of 6 to 60 carbon atoms and a single bond, and may be bonded to each other;
Y1 and Y2, which may be the same or different, are each independently selected from the group consisting of a substituted or unsubstituted aryl of 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 24 carbon atoms, a substituted or unsubstituted alkyl of 1 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl of 1 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 24 carbon atoms, cyano, halogen, a substituted or unsubstituted aryloxy of 6 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl of 6 to 60 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen, wherein adjacent substituents on Y1 and Y2 may form a fused, aliphatic, aromatic, heteroaliphatic or heteroaromatic ring; and
l and m are each an integer of 1 to 20, and n is an integer of 1 to 4;
A1, A2, E, and F may be the same or different, and are each independently a substituted or unsubstituted aromatic hydrocarbon of 6 to 50 carbon atoms or a substituted or unsubstituted heteroaromatic ring of 2 to 40 carbon atoms, wherein two adjacent carbon atoms of the aromatic ring A1 and two adjacent carbon atoms of the aromatic ring A2 form a 5-membered fused ring together with a carbon atom to which substituents R1 and R2 are bonded;
linkers L1 to L12 may be the same or different, and are each independently selected from among a single bond, a substituted or unsubstituted alkylene of 1 to 60 carbon atoms, a substituted or unsubstituted alkenylene of 2 to 60 carbon atoms, a substituted or unsubstituted alkynylene of 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene of 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene of 2 to 60 carbon atoms, a substituted or unsubstituted arylene of 6 to 60 carbon atoms, and a substituted or unsubstituted heteroarylene of 2 to 60 carbon atoms;
M is any one selected from among N—R3, CR4R5, SiR6R7, GeRsR9, O, S, and Se;
R1 to R9, and Ar1 to Ar8 may be the same or different, and are each independently any one selected from among hydrogen, deuterium, a substituted or unsubstituted alkyl of 1 to 30 carbon atoms, a substituted or unsubstituted aryl of 6 to 50 carbon atoms, a substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl of 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl of 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl of 5 to 30 carbon atoms, a substituted or unsubstituted heteroaryl of 2 to 50 carbon atoms, a substituted or unsubstituted heterocycloalkenyl of 2 to 30 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy of 1 to 30 carbon atoms, a substituted or unsubstituted aryl thioxy of 6 to 30 carbon atoms, a substituted or unsubstituted alkyl amine of 1 to 30 carbon atoms, a substituted or unsubstituted aryl amine of 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl of 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl of 5 to 30 carbon atoms, a substituted or unsubstituted alkyl germanium of 1 to 30 carbon atoms, a substituted or unsubstituted aryl germanium of 1 to 30 carbon atoms, a cyano, a nitro, and a halogen, with the proviso that R1 and R2 together may form a mono- or polycyclic aliphatic or aromatic ring, which may be a heterocyclic ring having a heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te as a ring member;
p1 to p4, r1 to r4, and s1 to s4 are each independently an integer of 1 to 3, with the proviso that when any of them is 2 or greater, the corresponding linkers L1 to L12 may be the same or different;
x is an integer of 1 or 2, and y and z may be the same or different and are each independently an integer of 0 to 3;
Ar1 may form a ring with Ar2, Ara may form a ring with Ar4, Ar5 may form a ring with Ar6, and Ar7 may form a ring with Ar8; and
two adjacent carbon atoms of the A2 ring occupy respective positions * of Structural Formula Q1 to form a fused ring; and
two adjacent carbon atoms of the A1 ring occupy respective positions * of Structural Formula Q2 to form a fused ring, and two adjacent carbon atoms of the A2 ring occupy respective positions * of Structural Formula Q1 to form a fused ring.

### Claim 8 (depends on 1)

The organic light-emitting diode of claim 1, further comprising a light-emitting layer, made of a blue light-emitting material, a green light-emitting material, or a red light-emitting material, which emits light in a wavelength range of 380 nm to 800 nm.

### Claim 9 (depends on 5)

The organic light-emitting diode of claim 5, wherein at least one of the layers is formed using a deposition process or a solution process.

### Claim 10 (depends on 1)

The organic light-emitting diode of claim 1, wherein the organic light-emitting diode is used for a device selected from among a flat display device; a flexible display device; a monochrome or white flat illumination device; and a monochrome or white flexible illumination device.