# US 2016/0254459 A1 · Organic electroluminescence device

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- Number: US 2016/0254459 A1
- Document ID: US20160254459A1
- Status: Published application
- Kind: A1
- Application number: 15/074,080
- Filed: 2016-03-18
- Published: 2016-09-01
- Earliest claimed: 2010-11-22
- Assignees: Idemitsu Kosan Co., Ltd.
- Applicants: Idemitsu Kosan Co., Ltd.
- Inventors: Yuichiro KAWAMURA; Hiroyuki SAITO; Hitoshi KUMA; Masahiro KAWAMURA; Yukitoshi JINDE; Hirokatsu ITO; Takayasu SADO; Sayaka MIZUTANI
- Web page: https://patentgrep.com/patent/US20160254459A1

## CPC

- C09K 11/06: containing organic luminescent materials
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/654: {comprising only nitrogen as heteroatom (H10K85/652 takes precedence)}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/6574: {comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes}
- H10K 85/6576: {comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene}
- 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 2211/1044: containing two nitrogen atoms as heteroatoms
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- H10K 50/12: comprising dopants
- H10K 50/15: Hole transporting layers
- H10K 50/171: {Electron injection layers}
- H10K 50/18: Carrier blocking layers
- H10K 85/611: {Charge transfer complexes}
- H10K 85/622: {containing four rings, e.g. pyrene}
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/655: {comprising only sulfur as heteroatom}
- H10K 2101/10: Triplet emission
- H10K 2101/40: Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An organic electroluminescence device that includes an anode, an emitting layer that includes a host and a fluorescent dopant, an electron transporting zone, a cathode, a blocking layer adjacent to the emitting layer in the electron transporting zone where the blocking layer includes an aromatic heterocyclic derivative with an azine ring and where the triplet energy ETb (eV) of the aromatic heterocyclic derivative is larger than a triplet energy ETh (eV) of the host.

## Claims

### Claim 1

An organic electroluminescence device, comprising in sequential order an anode, an emitting layer, a blocking layer, and a cathode, wherein
the emitting layer comprises a host and a fluorescent dopant,
the blocking layer comprises an aromatic heterocyclic derivative,
a triplet energy ETb (eV) of the aromatic heterocyclic derivative is larger than a triplet energy ETh (eV) of the host,
the aromatic heterocyclic derivative is represented by formula (BL-4), formula (BL-5) or formula (BL-6);
wherein in formula (BL-4), D1 to D4 each represent a cyclic structure being fused to form a D1 to D4 ring, at least one of D1 to D4 are structured to have a hetero atom, another fused ring optionally being formed in such a manner as to cross-couple the adjacent Ds in the D1 to D4 ring;
R represents a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, or residues of combination of two or more thereof;
when n is 1, R′ represents the same as R,
when n is 2 to 6, R′ represents a linking group selected from a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, and a substituted or unsubstituted heteroarylene group, and residues of combination of two or more thereof, or
R′ directly bonds two D1 to D4 rings in a single bond;
m is an integer of 0 to 11;
n is an integer of 1 to 5; and
when a plurality of D1 to D4 rings and Rs are present, the plurality of D1 to D4 rings and Rs are each the same or different,
wherein in the formula (BL-5), E1 to E4 each represent a cyclic structure being fused to form a E1 to E4 ring, at least one of E1 to E4 being structured to have a hetero atom, another fused ring optionally being formed in such a manner as to cross-couple the adjacent substituents on each of E1 to E4 in the E1 to E4 ring;
R represents a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, or residues of combination of two or more thereof;
R′ represents the same as R when n is 1,
R′ represents a linking group selected from a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, and residues of combination of two or more thereof when n is 2 to 6, or
R′ directly bonds two E1 to E4 rings in a single bond;
(m+1) is an integer of 0 to 11;
n is an integer of 1 to 5; and
when a plurality of E1 to E4 rings and Rs are present, the plurality of E1 to E4 rings and Rs each are the same or different,
wherein in the formula (BL-6) F1 to F5 each represent a cyclic structure being fused to form a F1 to F5 ring, at least one of F1 to F5 being structured to have a hetero atom, another fused ring optionally being formed in such a manner as to cross-couple adjacent substituents on each of F1 to F5 in the F1 to F5 ring;
R represents a group selected from a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, or residues of combination of two or more thereof;
R′ represents the same as R when n is 1,
R′ represents a linking group selected from a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, and a substituted or unsubstituted heteroarylene group, and residues of combination of two or more thereof when n is 2 to 6, or
R′ directly bonds two F1 to F5 rings in a single bond;
m is an integer of 0 to 13;
n is an integer of 1 to 5;
when a plurality of F1 to F5 rings and Rs are present, the plurality of F1 to F5 rings and Rs each are the same or different.

### Claim at position 2

2-14. (canceled)

### Claim 15 (depends on 1)

The organic electroluminescence device of claim 1, wherein the aromatic heterocyclic derivative is represented by the formula (BL-4).

### Claim 16 (depends on 15)

The organic electroluminescence device of claim 15, wherein the D1 to D4 ring is a fused ring structure represented by a structure selected from:
wherein X represents CR″ or N;
Y represents one of O, S, NR″ and C(R″)2, at least one of Y in a single structure is O, S or NR″;
Z represents CR″ or N, at least one Z is N; and
one R″ is a bonding portion to R′ and the other R″s each are a hydrogen atom or independently chosen from the substituents for R.

### Claim 17 (depends on 1)

The organic electroluminescence device of claim 1, wherein the aromatic heterocyclic derivative is represented by the formula (BL-5).

### Claim 18 (depends on 17)

The organic electroluminescence device of claim 17, wherein the E1 to E4 ring is a fused ring structure represented by a structure selected from:
wherein X represents CR″ or N;
Y represents one of O, S, NR″ and C(R″)2, at least one Y is in a single structure being O, S or NR″;
Z represents CR″ or N, at least one Z representing N; and
one R″ is a bonding portion to R′ and the other R″s each are a hydrogen atom or independently chosen from the substituents for R.

### Claim 19 (depends on 1)

The organic electroluminescence device of claim 1, wherein the aromatic heterocyclic derivative is represented by the formula (BL-6).

### Claim 20 (depends on 19)

The organic electroluminescence device of claim 19, wherein the F1 to F5 ring is a fused ring structure represented by a structure selected from:
wherein X represents CR″ or N;
Y represents one of O, S, NR″ and C(R″)2, at least one Y is in a single structure being O, S or NR″;
Z represents CR″ or N, at least one Z representing N; and
one R″ is a bonding portion to R′ and the other R″s each are a hydrogen atom or independently chosen from the substituents for R.

### Claim 21 (depends on 1)

The organic electroluminescence device of claim 1, wherein the triplet energy ETh (eV) of the host is less than a triplet energy ETd (eV) of the dopant.

### Claim 22 (depends on 1)

The organic electroluminescence device of claim 1, wherein the triplet energy ETb (eV) of the aromatic heterocyclic derivative and the triplet energy ETh (eV) of the host satisfy ETh+0.2<ETb.

### Claim 23 (depends on 1)

The organic electroluminescence device of claim 1, wherein the triplet energy ETb (eV) of the aromatic heterocyclic derivative is greater than a triplet energy ETalq (eV) of tris(8-quinolinolato)aluminum complex.

### Claim 24 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the dopant exhibits a fluorescent emission of a main peak wavelength of less than or equal to 550 nm.

### Claim 25 (depends on 1)

The organic electroluminescence device according to claim 1, wherein
a hole transporting zone is positioned between the anode and the emitting layer,
a hole transporting layer is adjacent to the emitting layer in the hole transporting zone, and
wherein a triplet energy ETho (eV) of the hole transporting layer is greater than the triplet energy ETh (eV) of the host.

### Claim 26 (depends on 1)

The organic electroluminescence device according to claim 1, wherein
an electron injecting layer is positioned between the blocking layer and the cathode,
the electron injecting layer is made of the same material as a material of the blocking layer, and
a donor is doped in the electron injecting layer.

### Claim 27 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the dopant is an aminopyrene derivative.

### Claim 28 (depends on 1)

The organic electroluminescence device according to claim 1, wherein
an electron injecting layer is positioned between the blocking layer and the cathode, and
the electron injecting layer is made of a material different from a material of the blocking layer.

### Claim 29 (depends on 15)

The organic electroluminescence device according to claim 15, wherein an electron injecting layer is positioned between the blocking layer and the cathode, and
an affinity Ab (eV) of the blocking layer and an affinity Ae (eV) of the electron injecting layer satisfy a relationship of Ae−Ab<0.2.

### Claim 30 (depends on 17)

The organic electroluminescence device according to claim 17, wherein
an electron injecting layer is positioned between the blocking layer and the cathode, and
an affinity Ab (eV) of the blocking layer and an affinity Ae (eV) of the electron injecting layer satisfy a relationship of Ae−Ab<0.2.

### Claim 31 (depends on 19)

The organic electroluminescence device according to claim 19, wherein
an electron injecting layer is positioned between the blocking layer and the cathode, and
an affinity Ab (eV) of the blocking layer and an affinity Ae (eV) of the electron injecting layer satisfy a relationship of Ae−Ab<0.2.

### Claim 32 (depends on 1)

The organic electroluminescence device according to claim 1, wherein n is 1.

### Claim 33 (depends on 1)

The organic electroluminescence device according to claim 1, wherein at least one R represents a group selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted pyrimidine group and a substituted or unsubstituted triazine group, or residues of combination of two or more thereof.

### Claim 34 (depends on 15)

The organic electroluminescence device according to claim 15, wherein n in the formula (BL-4) is 1.

### Claim 35 (depends on 15)

The organic electroluminescence device according to claim 15, wherein n in the formula (BL-4) is 1, and
at least one R in the formula (BL-4) represents a group selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted pyrimidine group and a substituted or unsubstituted triazine group, or residues of combination of two or more thereof.

### Claim 36 (depends on 17)

The organic electroluminescence device according to claim 17, wherein n in the formula (BL-5) is 1.

### Claim 37 (depends on 17)

The organic electroluminescence device according to claim 17, wherein n in the formula (BL-5) is 1, and
at least one R in the formula (BL-5) represents a group selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted pyrimidine group and a substituted or unsubstituted triazine group, or residues of combination of two or more thereof.

### Claim 38 (depends on 19)

The organic electroluminescence device according to claim 19, wherein n in the formula (BL-6) is 1.

### Claim 39 (depends on 19)

The organic electroluminescence device according to claim 19, wherein n in the formula (BL-6) is 1, and
at least one R in the formula (BL-6) represents a group selected from a substituted or unsubstituted aryl group, substituted or unsubstituted pyrimidine group and a substituted or unsubstituted triazine group, or residues of combination of two or more thereof.
