# US 2014/0151677 A1 · Aromatic amine derivative, and organic electroluminescent element containing same

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- Number: US 2014/0151677 A1
- Document ID: US20140151677A1
- Status: Published application
- Kind: A1
- Application number: 14/233,370
- Filed: 2012-07-23
- Published: 2014-06-05
- Earliest claimed: 2011-07-26
- Assignees: Idemitsu Kosan Co., Ltd.
- Inventors: Takushi Shiomi; Masami Watanabe; Mitsuru Eida
- Web page: https://patentgrep.com/patent/US20140151677A1

## CPC

- H10K 85/633: {comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom}
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C08G 61/12: Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G 61/124: {with a five-membered ring containing one nitrogen atom in the ring}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 85/631: {Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine}
- H10K 85/636: {comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom}
- H10K 85/6572: {comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole}
- H10K 85/791: {Starburst compounds}
- C08G 2261/124: alternating
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3162: Arylamines
- C08G 2261/3241: containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
- C08G 2261/411: Suzuki reactions
- C08G 2261/5222: electrofluorescent
- C08G 2261/95: Use in organic luminescent diodes
- C08K 5/18: with aromatically bound amino groups
- H10K 50/15: Hole transporting layers
- H10K 85/1135: {Polyethylene dioxythiophene [PEDOT]; Derivatives thereof}
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

An aromatic amine derivative represented by the following formula (1): wherein Z1 is a group represented by the following formula (2); Z2 is a group represented by the following formula (3) or (3′); and P and Q are independently a group represented by the following formula (4) or (5):

## Claims

### Claim 1

An aromatic amine derivative represented by the following formula (1):
[Z1nL1 (1)
wherein Z1 is a group represented by the following formula (2);
L1 is a linkage group, and may include one or more substituents; and
n is an integer of 2 to 10:
[Z2mL2 (2)
wherein Z2 is a group represented by the following formula (3) or (3′);
L2 is a linkage group, and may include one or more substituents;
L1 in the formula (1) bonds to any of Z2 and L2; and
m is an integer of 2 to 10:
wherein in the formulas (3) and (3′),
A is a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms or a group formed of plural rings;
A′ is a single bond, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms or a group formed of plural rings;
B is a single bond, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms or a group formed of plural rings;
C is a single bond, a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms or a group formed of plural rings;
P and Q are independently a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms, a group formed of plural rings or a group represented by the following formula (4) or (5);
L2 in the formula (3) bonds to any of A, B, C, P and Q, and L2 in the formula (3′) bonds to A′; and
k and l are independently an integer of 0 or 1, and k+l≦1:
wherein in the formula (4), X is —O—, —S—, or —N(Ra)—, Ra is an atom or a group selected from a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group including 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group of which the alkyl parts are each a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a triarylsilyl group of which the aryl parts are each a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms and a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 25 ring carbon atoms and a substituted or unsubstituted heteroaryl group including 5 to 24 ring atoms;
R1 and R2 are independently an atom or a group selected from a substituted or unsubstituted linear or branched alkyl group including 1 to 20 carbon atoms, a substituted or unsubstituted linear or branched alkenyl group including 2 to 15 carbon atoms, a substituted or unsubstituted cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group of which the alkyl parts are each a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms, a triarylsilyl group of which the aryl parts are each a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including a substituted or unsubstituted alkyl group including 1 to 20 carbon atoms and a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms, a substituted or unsubstituted heteroaryl group including 5 to 24 ring atoms, a halogen atom and a cyano group, and adjacent plural R1s, adjacent plural R2s, and/or adjacent R1 and R2 may bond to each other to form a saturated or unsaturated ring;
a and b are independently an integer of 0 to 3 and
Q1 and Q2 are independently a group including 5 to 25 atoms which forms a saturated or unsaturated ring;
in the formula (5), Ar1 and Ar2 are independently a substituted or unsubstituted aromatic hydrocarbon group including 6 to 25 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group including 5 to 25 ring atoms, and at least one of Ar1 and Ar2 is a group formed of plural rings including 9 to 40 ring carbon atoms or a fused aromatic ring group including 10 to 25 ring carbon atoms.

### Claim 2 (depends on 1)

The aromatic amine derivative according to claim 1, wherein one or more selected from L1, L2, A and A′ is a linkage group or a group comprising a group represented by any of the following formulas:
wherein R3 and R4 are independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group or a t-butyl group;
j is an integer of 2≦j≦20, plural R3s may be the same or different, and plural R4s may be the same or different:
wherein R5, R6, R7 and R8 are independently a hydrogen atom, a liner or branched alkyl group including 1 to 20 carbon atoms, a liner or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group including an alkyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms;
R5 and R6 and/or R7 and R8 may be bonded to each other to form a saturated or unsaturated ring;
x and y are an integer of 1≦x≦3 and an integer of 1≦y≦3, respectively, and when x is 2 or 3, plural R7s may be the same or different, and when y is 2 or 3, plural R8s may be the same or different:
wherein R9 is a hydrogen atom, a linear or branched alkyl group including 1 to 20 carbon atoms, a linear or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group including an alkyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms; and
z is an integer of 1≦z≦4, and when z is 2, 3 or 4, plural R9s may be the same or different:
wherein R10 and R11 are independently a hydrogen atom, a linear or branched alkyl group including 1 to 20 carbon atoms, a linear or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms;
plural R10s and/or plural R11s may be bonded to each other to form a saturated or unsaturated ring; and
c is an integer of 1≦c≦3, and when c is 2 or 3, plural R11s may be the same or different.

### Claim 3 (depends on 1)

The aromatic amine derivative according to claim 1, wherein one or more selected from L1, L2, A and A′ is a linkage group or a group comprising a group that interrupts conjugation between N atoms.

### Claim 4 (depends on 3)

The aromatic amine derivative according to claim 3, wherein the linkage group or the group comprising a group that interrupts conjugation between N atoms is a linkage group or a group comprising a group represented by any of the following formulas:
wherein R3 and R4 are independently a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group or a t-butyl group, and
j is an integer of 2≦j≦20, plural R3s may be the same or different, and plural R4s may be the same or different:
wherein R5, R6, R7 and R8 are independently a hydrogen atom, a linear or branched alkyl group including 1 to 20 carbon atoms, a linear or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl including an alkyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms;
R5 and R6 and/or R7 and R8 may be bonded to each other to form a saturated or unsaturated ring; and
x and y are an integer of 1≦x≦3 and an integer of 1≦y≦3, respectively, and when x is 2 or 3, plural R7s may be the same or different, and when y is 2 or 3, plural R8s may be the same or different:
wherein R9 is a hydrogen atom, a linear or branched alkyl group including 1 to 20 carbon atoms, a linear or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group including an alkyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms; and
z is an integer of 1≦z≦4, and when z is 2, 3 or 4, plural R9s may be the same or different:
wherein R10 and R11 are independently a hydrogen atom, a linear or branched alkyl group including 1 to 20 carbon atoms, a linear or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group including an alkyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms;
plural R10s and/or plural R11s may be bonded to each other to form a saturated or unsaturated ring; and
c is an integer of 1≦c≦3, and when c is 2 or 3, plural R11s may be the same or different.

### Claim 5 (depends on 1)

The aromatic amine derivative according to claim 1, wherein P and/or Q is independently a group represented by the following formula (6) or (7):
wherein R1, R2, a, b, Q1 and Q2 are as defined in the formula (4); and
X is —O—, —S—, or —N(Ra)—, and Ra is as defined in the formula (4).

### Claim 6 (depends on 1)

The aromatic amine derivative according to claim 1, wherein P and/or Q is independently a group represented by the following formula (8):
wherein R1, R2, a and b are as defined in the formula (4); and
X is —O—, —S—, or —N(Ra)—, and Ra is as defined in the formula (4).

### Claim 7 (depends on 1)

The aromatic amine derivative according to claim 1, wherein P and/or Q is independently a group represented by the following formula (8-1) or (8-2):
wherein R1, R2, a and b are as defined in the formula (4); and
X is —O—, —S—, or —N(Ra)—, and Ra is as defined in the formula (4).

### Claim 8 (depends on 1)

The aromatic amine derivative according to claim 1, wherein at least one of L1, L2, A, A′, B, C, P and Q is bonded to a group comprising a polymerizable functional group.

### Claim 9 (depends on 8)

The aromatic amine derivative according to claim 8, wherein the group comprising a polymerizable functional group is
a group comprising a vinyl group, a vinylidene group, a vinylene group or an ethynylene group represented by the following formula (i);
a group comprising a benzocyclobutene group represented by the following formula (ii);
a group comprising an N-maleimide group represented by the following formula (iii);
a group comprising a norbornenyl group represented by the following formula (iv);
a group comprising an acetylenyl group represented by the following formula (v); or
(vi) a group comprising a functional group capable of cyclopolymerization or ring-opening polymerization selected from the group consisting of a group including a substituted or unsubstituted norbornene skeleton other than a group represented by the formula (iv), a group including a substituted or unsubstituted epoxy group or an oxetane group, a functional group including a lactone structure or a lactam structure, a cyclooctatetraene group, a 1,5-cyclooctadiene group, a 1,ω-diene group, an O-divinylbenzene group and a 1,ω-diyne group:
wherein R12, R13 and R14 are independently a hydrogen atom, a fluorine atom, a substituted or unsubstituted linear or branched alkyl group including 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms;
L11 is a linkage group; and
h is an integer of 0 or 1, and when h is 0, L11 is a single bond:
wherein R15, R16, R17 and R18 are independently a hydrogen atom, a linear or branched alkyl group including 1 to 20 carbon atoms, a linear or branched alkenyl group including 2 to 20 carbon atoms, a cycloalkyl group including 3 to 20 carbon atoms, a trialkylsilyl group including an alkyl group including 1 to 20 carbon atoms, a triarylsilyl group including an aryl group including 6 to 24 ring carbon atoms, an alkylarylsilyl group including an alkyl group including 1 to 20 carbon atoms and an aryl group including 6 to 24 ring carbon atoms, an aryl group including 6 to 24 ring carbon atoms or a heteroaryl group including 5 to 24 ring atoms;
R15 and R16, R16 and R17, and/or R17 and R18 may be bonded to each other to form a saturated or unsaturated ring,
L11 is a linkage group; and
h is an integer of 0 or 1, and when h is 0, L11 is a single bond:
wherein L11 is a linkage group; and
h is an integer of 0 or 1, and when h is 0, L11 is a single bond:
wherein L11 is a linkage group; and
h is an integer of 0 or 1, and when h is 0, L11 is a single bond:
R19(L11)h— (v)
wherein R19 is a hydrogen atom, a substituted or unsubstituted linear or branched alkyl group including 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group including 6 to 24 ring carbon atoms,
L11 is a linkage group; and
h is an integer of 0 or 1, and when h is 0, L11 is a single bond.

### Claim 10 (depends on 1)

An organic electroluminescence device comprising one or more organic thin film layers including at least an emitting layer between a cathode and an anode, wherein at least one layer of the organic thin film layers comprises a polymer containing one or more types of repeating units derived from the aromatic amine derivative according to claim 1 and/or the amine derivative according to claim 1.

### Claim 11 (depends on 10)

The organic electroluminescence device according to claim 10, wherein
the organic thin film layers comprise at least one layer of a hole-transporting layer and a hole-injecting layer, and
the at least one layer of a hole-transporting layer and a hole-injecting layer comprises the polymer.