# US 11,444,246 B2 · Aromatic amine derivative, and organic electroluminescent element using same

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- Number: US 11,444,246 B2
- Document ID: US11444246B2
- Status: Granted
- Kind: B2
- Application number: 16/903,952
- Filed: 2020-06-17
- Published: 2020-10-08
- Granted: 2022-09-13
- Earliest claimed: 2012-08-31
- Assignees: Idemitsu Kosan Co., Ltd.
- Applicants: Idemitsu Kosan Co., Ltd.
- Inventors: Tomoki Kato; Takayasu Sado; Takahiro Fujiyama
- Web page: https://patentgrep.com/patent/US11444246B2

## CPC

- C07C 211/61: with at least one of the condensed ring systems formed by three or more rings
- C07C 217/80: having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C 217/92: the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
- C07C 255/58: containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 307/91: Dibenzofurans; Hydrogenated dibenzofurans
- C07D 333/76: Dibenzothiophenes
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C09B 11/04: derived from triarylmethanes {, i.e. central C-atom is substituted by amino, cyano, alkyl}
- C09B 57/00: Other synthetic dyes of known constitution
- C09B 57/008: {Triarylamine dyes containing no other chromophores}
- C09K 11/06: containing organic luminescent materials
- 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 85/6574: {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}
- C07C 2603/18: Fluorenes; Hydrogenated fluorenes
- C09K 2211/1011: Condensed systems
- C09K 2211/1014: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/1037: with sulfur
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1092: containing sulfur as the only heteroatom
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/17: Carrier injection layers
- H10K 50/81: Anodes
- H10K 50/82: Cathodes
- H10K 85/615: {Polycyclic condensed aromatic hydrocarbons, e.g. anthracene}
- H10K 85/626: {containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

An aromatic amine derivative represented by formula (1): wherein R1, R2, R3, L, Ar1, Ar2, k, m, and n are the same as defined in the specification, is useful as a material for an organic EL device and realizes an organic EL device with a high efficiency and a long lifetime even when driving it at a low voltage.

## Claims

### Claim 1

An organic electroluminescence device, comprising, in the order listed:
an anode;
a first hole transporting layer;
a second hole transporting layer;
a light emitting layer; and
a cathode;
wherein at least one of the first hole transporting layer and second hole transporting layer comprises an aromatic amine derivative represented by formula (1):
wherein in formula (1):
R1 each independently represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a phenyl group;
R2 and R3 each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms,
k represents an integer of 1 to 5;
m represents an integer of 1 to 4;
n represents an integer of 1 to 3;
when groups R1 exist, the groups R1 may be the same or different, when groups R2 exist, the groups R2 may be the same or different; and when groups R3 exist; the groups R3 may be the same or different;
L represents a single bond or a divalent group represented by formula (16):
wherein in formula (16):
R1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group;
m represents an integer of 1 to 4; and
when groups R1 exist, the groups R1 may be the same or different;
Ar1 represents a group represented by formula (30):
wherein in formula (30):
R1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group;
m represents an integer of 1 to 4;
when groups R1 exist, the groups R1 may be the same or different; and
two R4 may be the same or different and each independently represents a methyl group or a phenyl group;
Ar2 represents a group represented by formula (7):
wherein in formula (7):
R1 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a phenyl group;
k represents an integer of 1 to 5;
m represents an integer of 1 to 4; and
when groups R1 exist, the groups R1 may be the same or different.

### Claim 2 (depends on 1)

The organic electroluminescence device according to claim 1, wherein two R4 represent methyl groups.

### Claim 3 (depends on 1)

The organic electroluminescence device according to claim 1, wherein one of two R4 represents a methyl group and the other represents a phenyl group.

### Claim 4 (depends on 1)

The organic electroluminescence device according to claim 1, wherein two R4 represent phenyl groups.

### Claim 5 (depends on 1)

The organic electroluminescence device according to claim 1, wherein Ar2 represents a group represented by formula (7-1) or (7-2):
wherein R1, k and m are as defined in formulae (7).

### Claim 6 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1 in formula (1) each independently represents a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group or a phenyl group.

### Claim 7 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1 in formula (30) represents a hydrogen atom or a phenyl group.

### Claim 8 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1 in formula (7) represents a hydrogen atom, a methyl group, a t-butyl group, or a phenyl group.

### Claim 9 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1, R2 and R3 in formula (1) represent hydrogen atoms.

### Claim 10 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1 in formula (16) represents a hydrogen atoms.

### Claim 11 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1 in formula (30) represents a hydrogen atom.

### Claim 12 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1 in formula (7) represents a hydrogen atom.

### Claim 13 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1, R2 and R3 in formula (1), R1 in formula (16), R1 in formula (30), and R1 in formula (7) represent hydrogen atoms.

### Claim 14 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the aromatic amine derivative is any one of the following compounds:

### Claim 15 (depends on 1)

The organic electroluminescence device according to claim 1, wherein the first hole transporting layer comprises the aromatic amine derivative.

### Claim 16 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R2 and R3 in formula (1) each independently represents a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a s-butyl group, or a t-butyl group.

### Claim 17 (depends on 1)

The organic electroluminescence device according to claim 1, wherein R1 in formula (1) each independently represents a hydrogen atom or a phenyl group.

### Claim 18 (depends on 1)

The organic electroluminescence device according to claim 1, wherein in (R1)m of formula (1):
R1 represents a phenyl group and m represents 1; and
wherein in (R1)n of formula (1):
R1 represents a hydrogen atom and n represents 3.