KR102081627B1 - Aromatic amine derivatives having fluorenyl moiety and organic light-emitting diode including the same - Google Patents

Abstract

상기 [화학식 A]에서, X₁ 내지 X₈ 과 Ar₁, Ar₂는 발명의 상세한 설명에 정의된 바와 같다.The present invention relates to an amine derivative having a fluorene group and an organic light emitting device including the same, and more particularly, to an organic light emitting device compound represented by the following [Formula A] and an organic light emitting device including the same.
[Formula A]

In [Formula A], X ₁ to X ₈ and Ar ₁ , Ar ₂ are as defined in the detailed description of the invention.

Description

Aromatic amine derivatives having fluorenyl moiety and organic light-emitting diode including the same}

The present invention relates to an aromatic amine derivative having a fluorene structure and an organic light emitting device including the same, and more particularly, to an aromatic amine derivative for an organic light emitting device that exhibits excellent luminous efficiency as compared to a conventional device and an organic containing the same. It relates to a light emitting device.

The organic light emitting diode is a self-luminous device and has fast response characteristics and a wide viewing angle, so that a clear video can be realized outdoors. In addition, since it is driven at low power, it is actively researched as a next-generation display device because it has elements capable of environment-friendly and flexible display devices, and recently, applications as lighting devices are expected.

An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows. Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a single molecule type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be.

On the other hand, when only one material is used as the light emitting material, the maximum light emission wavelength is shifted to the long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.

The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby improving efficiency. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

On the other hand, as a prior art for improving the efficiency of the organic light emitting device is disclosed in Japanese Patent Laid-Open No. 10-2012-0029446 discloses a technique related to the organic light emitting device of the amine derivative containing benzo fluorene, 10-2012-0083203 describes a technique related to an organic light emitting device containing an indenophenanthrene derivative.

However, despite the manufacture of various kinds of compounds for use in the light emitting medium layer, including the prior art, there is a continuing need for the development of organic materials for organic light emitting devices that exhibit stable and high efficiency device characteristics. It is true.

Publication No. 10-2012-0029446 (2012.03.26)

Publication No. 10-2012-0083203 (2012.07.25)

The first object of the present invention is to provide an organic compound which can be used in the light emitting layer of the organic light emitting device and excellent in luminous efficiency.

A second object of the present invention is to provide an organic light emitting device comprising the compound.

The present invention provides a amine derivative represented by the general formula (A) as a compound that can be used in the light emitting layer of the organic light emitting device to achieve the above technical problem.

[Formula A]

In [Formula A],

Ar ₁ and Ar ₂ are the same or different and are each independently a aryl having 6 to 20 carbon atoms including a halogen, cyano group, halogenated alkyl group, nitro group, carbonyl group, substituted or unsubstituted silyl group, or substituted or unsubstituted germanium group group; And a heteroaryl group having 3 to 20 carbon atoms, including a halogen, a cyano group, a halogenated alkyl group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted germanium group, or a nitrogen atom in an aromatic ring; Any one selected, and Ar ₁ and Ar ₂ may be bonded to each other to form a ring;

X ₁ to X ₈ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-30 alkyl group, a substituted or unsubstituted C2-30 alkenyl group, a substituted or unsubstituted C3-30 Cycloalkyl group, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted Alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted arylamine group having 5 to 30 carbon atoms , Substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, substituted or unsubstituted silyl group, substituted Unsubstituted germanium group, substituted or unsubstituted boron group, substituted or unsubstituted aluminum group, carbonyl group, phosphoryl group, amino group, nitrile group, hydroxy group, nitro group, halogen group, selenium group, tellurium group, amide group and Any one selected from the group consisting of an ester group, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero, or aromatic hetero group with adjacent groups;

At least one of X ₁ to X ₈ is a substituent represented by the structural formula Y1.

 [Structure Formula Y1]

In the above Y1,

'*' Means a bonding site capable of bonding to Formula A at X ₁ to X ₈ , wherein L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted C 2 to 30 Alkenylene group, or a single bond,

m is an integer from 0 to 2, and when m is 2, each L is the same or different,

A and B are each a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a condensed ring of a group adjacent to each other with an aliphatic, aromatic, aliphatic hetero, or aromatic hetero Can be formed.

According to the present invention, the compound represented by [Formula A] has an advantage that can be applied to the light emitting layer of the organic light emitting device by having a device characteristic excellent in the luminous efficiency to the existing material.

1 is a schematic diagram of an organic light emitting device according to an embodiment of the present invention.
2 is a diagram illustrating a light emission spectrum of an organic light emitting device including an aromatic amine derivative prepared according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The present invention provides an aromatic amine derivative represented by the following [Formula A] as an organic compound that can be used in the light emitting layer of the organic light emitting device.

[Formula A]

In [Formula A],

Ar ₁ and Ar ₂ are the same or different and are each independently a aryl having 6 to 20 carbon atoms including a halogen, cyano group, halogenated alkyl group, nitro group, carbonyl group, substituted or unsubstituted silyl group, or substituted or unsubstituted germanium group group; And a heteroaryl group having 3 to 20 carbon atoms, including a halogen, a cyano group, a halogenated alkyl group, a nitro group, a carbonyl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted germanium group, or a nitrogen atom in an aromatic ring; Any one selected, and Ar ₁ and Ar ₂ may be bonded to each other to form a ring;

X ₁ to X ₈ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-30 alkyl group, a substituted or unsubstituted C2-30 alkenyl group, a substituted or unsubstituted C3-30 Cycloalkyl group, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted Alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, substituted or unsubstituted arylamine group having 5 to 30 carbon atoms , Substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, substituted or unsubstituted silyl group, substituted Unsubstituted germanium group, substituted or unsubstituted boron group, substituted or unsubstituted aluminum group, carbonyl group, phosphoryl group, amino group, nitrile group, hydroxy group, nitro group, halogen group, selenium group, tellurium group, amide group and Any one selected from the group consisting of an ester group, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero, or aromatic hetero group with adjacent groups;

At least one of X ₁ to X ₈ is a substituent represented by the structural formula Y1.

 [Structure Formula Y1]

In the above Y1,

'*' Means a bonding site capable of bonding to Formula A at X ₁ to X ₈ , wherein L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted C 2 to 30 Alkenylene group, or a single bond,

m is an integer from 0 to 2, and when m is 2, each L is the same or different,

A and B are each a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and a condensed ring of a group adjacent to each other with an aliphatic, aromatic, aliphatic hetero, or aromatic hetero Can be formed.

Here, the 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, of 1 to 24 carbon atoms Alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, or C2-C24 hetero Arylalkyl group, a C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 hetero arylamino group, C1-C24 alkylsilyl group, C1-C24 It means substituted with one or more substituents selected from the group consisting of an arylsilyl group, an aryloxy group having 1 to 24 carbon atoms.

The aryl group used in the compound of the present invention means an aromatic system including one or more rings, and when such substituents are present, may be fused with neighboring substituents to further form a ring.

Specific examples of the aryl group include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl, and the like, and at least one hydrogen atom of the aryl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, Amino groups (—NH 2, —NH (R), —N (R ′) (R ″), R ′ and R ″ are independently of each other an alkyl group having 1 to 10 carbon atoms, in this case referred to as an “alkylamino group”), Amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, carbon number It may be substituted with a heteroalkyl group having 1 to 24, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms.

Heteroaryl group which is a substituent used in the compound of the present invention means a ring aromatic system having 2 to 24 carbon atoms containing 1, 2 or 3 hetero atoms selected from N, O, P or S, the remaining ring atoms are carbon, The rings may be fused to form a ring. At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like. The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like. At least one hydrogen atom of the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group which is a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl and methylcyclo Butylsilyl, dimethylfurylsilyl, and the like, and at least one hydrogen atom in the silyl group may be substituted with the same substituent as in the case of the aryl group.

The present invention is characterized in that the substituents Ar ₁ and Ar ₂ in the aromatic amine derivative having a fluorene structure represented by Formula A are an aryl group or a heteroaryl group substituted with an electron withdrawing group.

The electron withdrawing group is a functional group capable of attracting electrons in a molecule, for example, halogen, cyano group, halogenated alkyl group, nitro group, carbonyl group, substituted or unsubstituted silyl group, substituted or unsubstituted And germanium groups of the ring.

In addition, in the case of the heteroaryl group containing nitrogen in the aromatic ring, since the heteroaryl group containing nitrogen in the ring itself has an electron withdrawing property, it may also be included in the electron withdrawing group.

More specifically, in Formula A of the present invention, the substituents Ar ₁ and Ar ₂ are an aryl group having 6 to 20 carbon atoms including a silyl group having a halogen, a cyano group, a halogenated alkyl group, a nitro group, a carbonyl group or a halogenated alkyl group; Or a heteroaryl group having 3 to 20 carbon atoms, including a silyl group having a halogen, a cyano group, a halogenated alkyl group, a nitro group, a carbonyl group, or a halogenated alkyl group, or a nitrogen atom in an aromatic ring; Preferably, a fluorine, cyano group, halogenated alkyl group, or heteroaryl group containing nitrogen in the aromatic ring may be used as the electron withdrawing group.

When these electron withdrawing groups are substituted with an aryl group or a heteroaryl group, the aromatic amine having the fluorene structure of the present invention traps excess electrons so that holes and electrons can efficiently form excitons in the light emitting layer, thereby increasing efficiency. It is estimated.

More specifically, in the compound of the present invention, the substituents X ₁ to X ₈ in [Formula A] are the same or different and are each independently hydrogen; heavy hydrogen; Halogen atom; Hydroxyl group; Cyano group; Nitro group; Amino group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; Substituted or unsubstituted C2-C20 alkynyl group; A substituent of Formulas 4A to 4H; One of X ₁ to X ₈ may be an aromatic amine derivative which is a substituent represented by the structural formula Y1.

Wherein Z ₁ to Z ₇ of Formulas 4A to 4H are each independently hydrogen; heavy hydrogen; Halogen atom; Hydroxyl group; Cyano group; Nitro group; Amino group; Amidino groups; Hydrazine; Hydrazone; Carboxyl groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid or salts thereof; An alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; Alkylthio groups having 1 to 10 carbon atoms; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof and phosphoric acid or salt thereof having 1 to 10 carbon atoms An alkyl group, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms; Phenyl group; Naphthyl group; Fluorenyl group; Phenanthrenyl group; Anthryl group; Pyrenyl group; Chrysenyl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group having 1 to 10 carbon atoms, carbon number 1 Phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthryl group, pyrenyl group and chrysenyl group substituted with at least one of alkoxy group having 10 to 10 and alkylthio group having 1 to 10 carbon atoms; Indolyl group; Benzimidazolyl group; Carbazolyl groups; Imidazolyl group; Imidazolinyl group; Imidazopyridinyl group; Imidazopyrimidinyl group; Pyridinyl group; Pyrimidinyl group; Triazinyl group; Quinolinyl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group having 1 to 10 carbon atoms, carbon number 1 Indolyl group, benzoimidazolyl group, carbazolyl group, imidazolyl group, imidazolinyl group, imidazopyridinyl group substituted with at least one of an alkoxy group having 10 to 10, an alkylthio group phenyl group having 1 to 10 carbon atoms, and a naphthyl group , Imidazopyrimidinyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and quinolinyl group; Di (alkyl having 1 to 10 carbon atoms) amino group; And a di (aryl) amino group having 1 to 10 carbon atoms, and the aryl group having 6 to 10 carbon atoms may be a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a crysenyl group. It is any one selected from.

In the present invention, at least one of X ₁ to X ₄ and at least one of X ₅ to X ₈ in Chemical Formula A may be a substituent represented by the structural formula Y1.

In this case, the compound of [Formula A] in the present invention may be an aromatic amine derivative represented by any one selected from the following [Formula 1A-1] to [Formula 1G-4].

[Formula 1A-1] [Formula 1A-2] [Formula 1A-3]

[Formula 1A-4] [Formula 1A-5] [Formula 1A-6]

[Formula 1B-1] [Formula 1B-2] [Formula 1C-1]

 [Formula 1C-2] [Formula 1C-3] [Formula 1D-1]

[Formula 1D-2] [Formula 1D-3] [Formula 1D-4]

[Formula 1D-5] [Formula 1D-6] [Formula 1E-1]

 [Formula 1E-2] [Formula 1E-3] [Formula 1E-4]

[Formula 1E-5] [Formula 1F-1] [Formula 1F-2]

[Formula 1F-3] [Formula 1F-4] [Formula 1G-1]

 [Formula 1G-2] [Formula 1G-3] [Formula 1G-4]

Ar ₁ to Ar ₄ in [Formula 1A-1] to [Formula 1G-4] are the same substituents as Ar ₁ and Ar ₂ defined in [Formula A], wherein X ₁ to X ₂₄ are the above Formula [A] Same as X ₁ to X ₈ as defined in;

In addition, in [Formula 1A-1] to [Formula 1A-6] and [Formula 1B-1] to [Formula 1B-2], at least one of X ₁ to X ₄ and at least one of X ₅ to X ₁₂ are the above-mentioned. Structural formula Y1; In Formulas 1C-1 to 1C-3, at least one of X ₁ to X ₄ and at least one of X ₅ to X ₁₀ are the structural formulas Y1; In Formula 1D-1 to Formula 1D- ₆ , at least one of X ₁ to X ₆ and at least one of X ₇ to X ₁₂ are the structural formula Y1; In Formula 1E-1, at least one of X ₁ to X ₄ and at least one of X ₆ to X ₉ are the structural formula Y1; In Formulas 1E-2 to 1E-3, at least one of X ₁ to X ₄ and at least one of X ₇ to X ₁₀ are the structural formula Y1; In Formula 1E-4, at least one of X ₁ to X ₆ and at least one of X ₈ to X ₁₁ are the structural formula Y1; In Formula 1E-5, at least one of X ₁ to X ₆ and at least one of X ₉ to X ₁₂ are the structural formula Y1; In Formula 1F-1 to Formula 1F-2, at least one of X ₁ to X ₄ and at least one of X ₅ to X ₁₂ are the structural formula Y1; and [Formula 1F-3] to [Formula 1F] [4] and [Formula 1G-1] to [Formula 1G-3], at least one of X ₁ to X ₄ and at least one of X ₅ to X ₁₄ is the structural formula Y1; In Formula 1G-4, at least one of X ₁ to X ₄ and at least one of X ₅ to X ₂₄ may be the structural formula Y1.

In this case, the present invention may be represented by any one of the substituents Ar ₁ to Ar ₄ of the formula A selected from the following substituents A1 to A45.

[A substituent A1] [A substituent A2] [A substituent A3]

[A substituent A4] [A substituent A5] [A substituent A6]

[A substituent A7] [A substituent A8] [A substituent A9]

[A substituent A10] [A substituent A11] [A substituent A12]

[A substituent A13] [A substituent A14] [A substituent A15]

[A substituent A16] [A substituent A17] [A substituent A18]

[A substituent A19] [A substituent A20] [A substituent A21]

[A substituent A22] [A substituent A23] [A substituent A24]

[A substituent A25] [A substituent A26] [A substituent A27]

[A substituent A28] [A substituent A29] [A substituent A30]

[A substituent A31] [A substituent A32] [A substituent A33]

[A substituent A34] [A substituent A35] [A substituent A36]

[Substituent A37] [Substituent A38] [Substituent A39]

[A substituent A40] [A substituent A41] [A substituent A42]

 [A substituent A43] [A substituent A44] [A substituent A45]

Herein, '*' of the substituents A1 to A45 means a binding site bonded to a position of Ar ₁ to Ar ₄ of Formula A.

In another aspect, the present invention provides an aromatic amine derivative containing only two substituents represented by the formula (A).

In addition, in the present invention, substituents A and B of the structural formula Y1 substituted in Formula A may be any one selected from the following substituents B1 to B46.

[Substituent B1] [substituent B2] [substituent B3]

[Substituent B4] [substituent B5] [substituent B6]

[Substituent B7] [Substituent B8] [Substituent B9]

[Substituent B10] [Substituent B11] [Substituent B12]

[Substituent B13] [Substituent B14] [Substituent B15]

[Substituent B16] [Substituent B17] [Substituent B18]

[Substituent B19] [Substituent B20] [Substituent B21]

[Substituent B22] [Substituent B23] [Substituent B24]

[Substituent B25] [Substituent B26] [Substituent B27]

[Substituent B28] [Substituent B29] [Substituent B30]

[Substituent B31] [Substituent B32] [Substituent B33]

[Substituent B34] [Substituent B35] [Substituent B36]

[Substituent B37] [Substituent B38] [Substituent B39]

[Substituent B40] [Substituent B41] [Substituent B42]

[Substituent B43] [Substituent B44] [Substituent B45]

[Substituent B46]

Here, R of the substituents B1 to B46 are the same or different and independently of each other, hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or its Salts, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number 6 To 60 aryl group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted carbon atoms 2 to A heteroaryl group of 60, a substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), or (substituted or unsubstituted aryl having 6 to 60 carbon atoms ) Amino group, di (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus , Boron, and n is an integer of 0 to 12, each substituent may be fused with a group adjacent to each other to form a ring.

More specifically, the aromatic amine derivative compound of [Formula A] of the present invention may be any one selected from the group represented by the following formula H1 to formula H46.

Wherein the following formula '-D' means that the hydrogen site of the aromatic ring is substituted with deuterium.

[Formula H1] [Formula H2] [Formula H3]

[Formula H4] [Formula H5] [Formula H6]

[Formula H7] [Formula H8] [Formula H9]

[Formula H10] [Formula H11] [Formula H12]

[Formula H13] [Formula H14] [Formula H15]

[Formula H16] [Formula H17] [Formula H18]

Formula H19 Formula H20 Formula H21

[Formula H22] [Formula H23] [Formula H24]

[Formula H25] [Formula H26] [Formula H27]

Formula H28 Formula H29 Formula H30

[Formula H31] [Formula H32] [Formula H33]

[Formula H34] [Formula H35] [Formula H36]

[Formula H37] [Formula H38] [Formula H39]

[Formula H40] [Formula H41] [Formula H42]

[Formula H43] [Formula H44] [Formula H45]

[Formula H46]

In addition, the present invention is a first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one aromatic amine derivative in the present invention.

In the present invention, "(organic layer) includes one or more compounds" means "(organic layer) may include one compound belonging to the scope of the present invention or two or more different compounds belonging to the category of the compound. It can be interpreted as ".

In this case, the organic layer including the aromatic amine derivative of the present invention may include at least one of a hole injection layer, a hole transport layer, a hole injection function and a hole injection function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. have.

In addition, in the present invention, the organic layer interposed between the first electrode and the second electrode may be a light emitting layer, and in this case, the light emitting layer may be formed of a host and a dopant.

Generally, as the host used in the light emitting layer, Alq3, CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole)), 9,10-di ( Naphthalen-2-yl) anthracene (ADN), TCTA, TPBI (1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene (1,3,5-tris (N-phenyl benzimidazol-2 -yl) benzene)), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3, DSA (distyrylarylene), dmCBP and the host described above Deuterium substituents of the compounds may be used, but is not limited thereto.

When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

Meanwhile, in the present invention, one or more layers selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer may be formed by a single molecule deposition method or a solution process. The organic light emitting device can be used for a display device, a display device, or a device for monochrome or white illumination.

As a specific example of the present invention, a hole transport layer (HTL) is further stacked between the anode and the organic light emitting layer, and an electron transport layer (ETL) is added between the cathode and the organic light emitting layer. The hole transport layer may be stacked to facilitate the injection of holes from the anode. As the material of the hole transport layer, electron donating molecules having a small ionization potential are used, mainly triphenylamine. Many diamine, triamine, or tetraamine derivatives are used.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1- Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenylbenzidine (a-NPD) and the like can be used.

A hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc (copperphthalocyanine) or starburst amines TCTA (4,4 ', 4 "-tri (N-carbazolyl) triphenyl-amine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenyl amino) riphenylamine) and the like can be used.

In addition, the electron transport layer used in the organic light emitting device according to the present invention provides an opportunity to recombine within the light emitting layer by smoothly transporting the electrons supplied from the cathode to the organic light emitting layer and suppressing the movement of holes not combined in the organic light emitting layer. It acts to increase.

The electron transport layer material may be used without particular limitation as long as it is commonly used in the art. For example, as described above, an oxadiazole derivative such as PBD, BMD, BND or Alq ₃ may be used. Can be.

Meanwhile, an electron injection layer (EIL) may be further stacked on the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, materials such as LiF, NaCl, CsF, Li ₂ O, BaO may be used.

Hereinafter, the organic light emitting diode of the present invention will be described with reference to FIG. 1.

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, if necessary, the hole injection layer 30 and the electron The injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to Figure 1 with respect to the organic light emitting device and a manufacturing method of the present invention. First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the anode electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum-heat deposition or spin coating the hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30.

Subsequently, the organic light emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by vacuum deposition or spin coating. can do. The hole blocking layer prevents such a problem by using a material having a very low highest Occupied Molecular Orbital (HOMO) level because when the hole is introduced into the cathode through the organic light emitting layer is reduced the lifetime and efficiency of the device. . In this case, the hole blocking material to be used is not particularly limited, but should have an ionization potential higher than that of the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a cathode forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form a cathode 80 electrode. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

In addition, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa, and the light emitting layer may be made of a host and a dopant, and the compound of the present invention may be used as a dopant.

In this case, the host layer may be an anthracene derivative represented by the following [Formula B]. In this case, the emission layer may further include various host materials.

[Formula B]

In Formula B,

Ar _{7 ,} Ar ₈ and Ar ₉ are the same as or different from each other, and each independently, a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linking group, or a substituted or unsubstituted C ₂ -C ₆₀ heteroaromatic linking group;

R ₂₁ to R ₃₀ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or Salts thereof, phosphoric acid or salts thereof, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl groups having 2 to 60 carbon atoms, substituted or unsubstituted Substituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted aryl having 6 to 60 carbon atoms A group, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), or (substituted or unsubstituted aryl having 6 to 60 carbon atoms), di (substituted Or an unsubstituted aryl) amino group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus and boron. Each substituent may form a condensed ring with a group adjacent to each other;

E, f and g are the same as or different from each other, and each independently an integer of 0 to 4;

The two sites represented by * of the anthracene may be the same or different from each other, and may be independently bonded to the P or Q structure to form an anthracene-based derivative selected from the following Chemical Formulas 1Aa-1 to 1Aa-3.

[Formula 1Aa-1] [Formula 1Aa-2] [Formula 1Aa-3]

Here, the 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, of 1 to 24 carbon atoms Alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, or C2-C24 hetero Arylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 heteroarylamino group, C1-C24 alkylsilyl group, C1-C24 It means substituted with one or more substituents selected from the group consisting of an arylsilyl group, an aryloxy group having 1 to 24 carbon atoms.

Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to illustrate the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited thereby.

<Example>

Synthesis Example 1 Synthesis of BD1

Synthesis Example 1-1. Synthesis of Intermediate 1-a

Intermediate 1-a was synthesized according to Scheme 1 below.

<Scheme 1>

                                            <Intermediate 1-a>

50 g (194 mmol) of 9-bromo phenanthrene was placed in a round bottom flask containing 500 ml of tetrahydrofuran, and the temperature was adjusted to -78 ° C under a nitrogen atmosphere. After 30 minutes, 146 ml (233 mmol) of normalbutyllithium was slowly added dropwise, and after 1 hour, 28.3 g (274 mmol) of trimethylborate was slowly added dropwise, and the temperature was raised to room temperature. After stirring for about 12 hours at room temperature, 2N (normal) hydrochloric acid aqueous solution was added dropwise to the reaction solution until the acid, extracted, and the organic layer was collected and distilled under reduced pressure. Recrystallization with normal nucleic acid, followed by filtration and drying, yielded 35 g of intermediate 1-a (yield 81%) as a white solid.

Synthesis Example 1-2. Synthesis of Intermediate 1-b

Intermediate 1-b was synthesized according to Scheme 2 below.

<Scheme 2>

                                           <Intermediate 1-b>

In a round bottom flask, 24 g (112 mmol) of methyl 2-bromobenzoate, 34.7 g (0.156 mmol) of intermediate 1-a, tetrakistriphenylphosphinepalladium {Pd (PPh ₃ ) ₄ } 2.6 g (2 mmol), 30.9 g (223 mmol) of potassium carbonate, 50 mL of water, 125 ml of toluene and 125 mL of tetrahydrofuran were added thereto, and the mixture was refluxed for 12 hours. After completion of the reaction, the reactants were separated by layer, the organic layer was concentrated under reduced pressure, separated by column and dried to obtain 25 g (yield 72%) of intermediate 1-b as a white solid.

Synthesis Example 1-3. Synthesis of Intermediate 1-c

According to Scheme 3 below, Intermediate 1-c was synthesized.

<Scheme 3>

                                                   <Intermediate 1-c>

39.2 g (224 mmol) of 1-bromo-3-fluorobenzene was added to a round bottom flask under nitrogen stream, followed by 200 mL of tetrahydrofuran, followed by cooling to -78 ° C. 130 mL of normal-butyllithium was slowly added dropwise to the cooled reaction solution, followed by stirring for about 30 minutes at the same temperature. 25.0 g (80 mmol) of Intermediate 1-b was added thereto, followed by stirring at room temperature for 30 minutes to 1 hour. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic layer was separated and concentrated under reduced pressure. Concentrate with hexane to crystallize and filter. 33 g (87% yield) of intermediate 1-c was obtained as a light yellow solid.

Synthesis Example 1-4. Synthesis of Intermediate 1-d

According to Scheme 4, intermediate 1-d was synthesized:

<Scheme 4>

                                                      <Intermediate 1-d>

To a round bottom flask, 33 g (70 mmol) of Intermediate 1-c, 270 mL of acetic acid and 0.2 mL of hydrochloric acid were added dropwise and heated to 80 ° C. After the reaction, the mixture was reacted for 3 to 6 hours, and the resulting composite was filtered and washed with water and methanol. The obtained solid was dissolved in dichloromethane and crystallized with acetone to obtain 27 g of intermediate 1-d (yield 85%) as a white solid.

Synthesis Example 1-5. Synthesis of Intermediate 1-e

According to Scheme 5 below, Intermediate 1-e was synthesized.

Scheme 5

                                              <Intermediate 1-e>

Dissolve 27 g (59 mmol) of Intermediate 1-d and 220 mL of chloroform in a round bottom flask. A solution of 26.6 g of bromine and 60 mL of chloroform was added dropwise to the clean solution, followed by stirring at room temperature for 48 hours. After the reaction was completed, 80 mL of aqueous sodium bicarbonate solution was added dropwise and stirred for 30 minutes. After stirring, the mixture was washed with methanol and acetone while filtering. The obtained solid was dissolved in 1,2-dichlorobenzene, cooled, and filtered four times in the same manner to obtain 16 g of intermediate 1-e (yield 44%) as a white solid.

Synthesis Example 1-6. Synthesis of BD1

According to Scheme 6 below, BD1 was synthesized.

<Scheme 6>

                                                            <BD1>

10.4 g (17 mmol) of intermediate 1-e, 7.6 g (45 mmol) of diphenylamine, palladium acetate {Pd (OAc) ₂ } 0.2 g (0.7 mmol), 6.7 g of sodium tert-butoxide in a round bottom flask mmol), tritary butylphosphine 0.14 g (0.7 mmol) and 100 mL of toluene were added and reacted at a reaction temperature of 100 ° C. for 2 hours. After the reaction was completed, the filtrate was concentrated after the filter and separated by column chromatography. The solid produced by recrystallization from toluene was filtered and dried to obtain 5 g (37% yield) of BD1 as a pale yellow solid.

MS (MALDI-TOF): m / z 789 [M] ⁺ . ¹³ CNMR (75MHz, CDCl ₃ ) δ: 61.6, 109.0, 113.0, 115.2, 120.7, 121.0, 122.1, 122.4, 125.7, 126.6, 126.8, 127.5, 127.6, 128.3, 129.0, 129.2, 129.4, 129.6, 130.8, 131.7, 134.6, 135.4, 139.4, 140.0, 140.3, 142.8, 145.9, 149.3, 163.4 [57C]

Synthesis Example 2 Synthesis of BD2

The same method as in Synthesis Example 1 except for using 1-bromo-3,5-difluorobenzene instead of 1-bromo-3-fluorobenzene used in <Scheme 3> of Synthesis Example 1-3. 4.5 g (yield 33%) of BD2 as a pale yellow solid was obtained.

MS (MALDI-TOF): m / z 825 [M] ⁺ . ¹³ CNMR (75MHz, CDCl ₃ ) δ: 61.6,102.2,109,110.8,120.7,121,122.1,122.4,125.7,126.6,126.8,127.6,128.3,129,129.2,129.4,129.6,131.7,134.6,135.4,139.4,140,140.3,142.8, 145.9,150.9,163.7 [57C]

Synthesis Example 3 Synthesis of BD3

The same method as in Synthesis Example 1 was repeated except that 1-bromo-4-trifluoromethylbenzene was used instead of 1-bromo-3-fluorobenzene used in <Scheme 3> of Synthesis Example 1-3. 5.2 g (yield 38%) of BD3 as a light yellow solid was obtained.

MS (MALDI-TOF): m / z 889 [M] ⁺ . ¹³ CNMR (75MHz, CDCl ₃ ) δ: 61.6, 109, 120.7, 121, 122.1, 122.4, 124.1, 125.6, 125.7, 126.6, 126.8, 127.6, 128.3, 128.5, 129, 129.2, 129.4, 129.6, 131.7, 134.6, 135.4, 139.4, 140, 140.3, 142.8, 145.9, 151 [59C]

Synthesis Example 4 Synthesis of BD4

BD4, which is a pale yellow solid, using the same method as in Synthesis Example 1, except that 3-bromopyridine was used instead of 1-bromo-3-fluorobenzene used in <Scheme 3> of Synthesis Example 1-3. 4.8 g (32% yield) were obtained.

MS (MALDI-TOF): m / z 755 [M] ⁺ . ¹³ CNMR (75MHz, CDCl ₃ ) δ: 61.6, 109, 120.7, 121, 122.1, 122.4, 124.1, 125.6, 125.7, 126.6, 126.8, 127.6, 128.3, 128.5, 129, 129.2, 129.4, 129.6, 131.7, 134.6, 135.4, 139.4, 140, 140.3, 142.8, 145.9, 151 [55C]

Synthesis Example 5 Synthesis of BD5

Except for using 2-bromo-4-methylpyridine in place of 1-bromo-3-fluorobenzene used in <Scheme 3> of Synthesis Example 1-3 using the same method as in Synthesis Example 1 5.0 g (yield 35%) of BD5 was obtained as a yellow solid.

MS (MALDI-TOF): m / z 783 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ: 21.6, 62.2, 109, 120.7, 121, 122.1, 122.4, 125.7, 126.6, 126.8, 127.6, 128.3, 129, 129.2, 129.4, 129.6, 131.7, 134.6, 135.4, 139.4, 140, 140.3, 142.8, 145.9, 147.5, 149.1, 159.1, 142.8, 145.9, 146.5, 152.3 [57C]

Synthesis Example 6 Synthesis of BD6

BD6 which is a pale yellow solid using the same method as in Synthesis Example 1, except that 3-bromoquinoline was used instead of 1-bromo-3-fluorobenzene used in <Scheme 3> of Synthesis Example 1-3. 4.5 g (37% yield) were obtained.

MS (MALDI-TOF): m / z 855 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ: 62.4, 109, 120.7, 121, 122.1, 122.4, 125.7, 126.6, 126.8, 127.6, 127.7, 128.3, 128.4, 128.5, 128.8, 129, 129.2, 129.4, 129.6, 130.1, 131.7, 134.6, 134.7, 135.4, 139.4, 140, 140.3, 149.3, 150.2, 163.4 [63C]

Synthesis Example 7. Synthesis of BD7

Synthesis Example 7-1. Synthesis of Di (4-cyanophenyl) amine

20.0 g (110 mmol) of 1-bromo-4-cyanobenzene, 14.3 g (121 mmol) of 4-cyanoaniline, 1.37 g (2.2 mmol) of BINAP, and 13.7 g (140 mmol) of sodium tert-butoxide mmol), palladium acetate (Pd (OAc) 2) 0.49 g (2.1 mmol), and 100 ml of toluene were added and refluxed for 24 hours. After the reaction is completed, the organic solvent is distilled under reduced pressure, and extracted with ethyl acetate and water. The organic layer is separated to remove the solvent, and the resulting solid is washed with methanol. Hexane and ethyl acetate (1: 3) were used as a developing solvent, and the residue was separated by column chromatography and dried to yield 18.6 g (yield 77%) of di (4-cyanophenyl) amine as a white solid.

Synthesis Example 7-2. Synthesis of BD7

In the same manner as in Synthesis Example 1-6 except that di (4-cyanophenyl) amine prepared in Synthesis Example 7-1 was used instead of the diphenylamine used in Synthesis Example 1-6. 5.5 g (yield 45%) of BD7 as a yellow solid was obtained.

MS (MALDI-TOF): m / z 889 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ: 61.6, 107, 109, 113, 115.2, 118.6, 120.7, 121, 122.1, 122.4, 123.4, 126.6, 127.5, 127.6, 128.3, 129, 129.2, 129.4, 130.8, 131.7, 133.1, 134.6, 135.4, 139.4, 140, 140.3, 142.8, 140, 140.3, 142.8, 145.7, 146.3, 149.3, 163.4 [61C]

Synthesis Example 8 Synthesis of BD8

Synthesis Example 8-1. Synthesis of 4- (tertiary-butyl) -N- (4- (trimethylsilyl) phenyl) aniline

(4-bromophenyl) trimethylsilane was used instead of 1-bromo-4-cyanobenzene used in Synthesis Example 7-1, and 4- (tertiary-butyl) aniline was used instead of 4-cyanoaniline. Except that 15 g (yield 70%) of 4- (tertiary-butyl) -N- (4- (trimethylsilyl) phenyl) aniline were obtained using the same method.

Synthesis Example 8-2. Synthesis of BD8

Except for using the 4- (tertiary-butyl) -N- (4- (trimethylsilyl) phenyl) aniline prepared in Synthesis Example 8-1 instead of the diphenylamine used in Synthesis Example 1-6 In the same manner as in Synthesis Example 1-6, 4.6 g (yield 41%) of BD8 as a light yellow solid was obtained.

MS (MALDI-TOF): m / z 1046 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ: 3, 31.3, 34.2, 61.6, 109, 113, 115.2, 120.7, 121, 122, 122.1, 122.4, 126.6, 127.5, 127.6, 128.3, 128.6, 129, 129.2, 129.4, 130.8, 131, 131.7, 134.5, 134.6, 135.4, 139.4 [71C]

Synthesis Example 9. Synthesis of BD9

BD9 4.0g (yield 31%) was obtained using the same method as Synthesis Example 1-2, except that 1-naphthylboronic acid was used instead of Intermediate 1-a used in Synthesis Example 1-2.

MS (MALDI-TOF): m / z 739 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ: 63.3, 107.8, 113, 115.2, 120.5, 120.7, 121, 122.1, 123.2, 123.9, 125.5, 125.7, 125.8, 126.8, 127.5, 128, 129.6, 130.8, 133.6, 134.4, 135.4, 140.1, 140.3, 142.8, 145.9, 149.3, 163.4 [53C]

Synthesis Example 10 Synthesis of BD 10

<Scheme 7>

   10-a 10-b BD10

In a round bottom flask of nitrogen atmosphere, intermediate 10-a 30 g (0.053 mol) prepared in Synthesis Example 9 and Chem. Lett. 41.2 g (0.128 mol) of Intermediate 10-b, 4,4 '-((4-vinylphenyl) azanediyl) dibenzonitrile, prepared by citing 2011, 40, 1036-1038] Dissolve in 500 mL. 1.2 g (0.005 mol) of Pd (OAc) ₂ , 2.8 g (0.011 mol) of triphenylphosphine and 14.7 g (0.107 mol) of calcium carbonate are added to the flask. Heat at 110 ° C. for 15 hours under a stream of nitrogen. After the reaction for 15 hours, the mixture is stirred at room temperature for 15 hours. Water of the organic layer extracted with water and ethyl acetate was removed with anhydrous magnesium sulfate, and the obtained organic layer was concentrated under reduced pressure and separated by column chromatography to obtain BD 10 40 g (72% yield).

MS (MALDI-TOF): m / z 1042 [M] ⁺ . ¹³ CNMR (75MHz, CDCl ₃ ) δ: 55.2,64.1,107,110.1,113,115.2,118.6,122.1,123.4,123.5,124.4,124.9,125.2,125.8,126.3,126.9,127.4,127.5,128.1,128.2,128.3,128.9, 129.1,129.5,129.7,130.8,132,132.7,132.8,133.1,133.6,133.7,134.8,135,138.2,140.2,141.8,142.6,145.1,147.7,149.3,149.8,150.2,163.4

Synthesis Example 11 Synthesis of Chemical Formula H3

Using the same method as in Synthesis Example 8 except for using 1-bromo-4- (tertiary-butyl) benzene instead of (4-bromophenyl) trimethylsilane used in Synthesis Example 8-1 3.6 g (yield 42%) of formula H2 were obtained.

MS (MALDI-TOF): m / z 1014 [M] ⁺ . ¹³ CNMR (75MHz, CDCl ₃ ) δ: 31.3, 34.2, 61.6, 109, 113, 115.2, 120.7, 121, 122.1, 122.4, 126.6, 127.5, 127.6, 128.3, 128.6, 129, 129.2, 129.4, 130.8, 131.7, 134.6, 135.4, 139.4, 140, 140.3, 142.8, 145.7, 149.3, 163.4 [73C]

Synthesis Example 12 Synthesis of Chemical Formula H19

2-bromoanthracene was used instead of 9-bromo phenanthrene used in Synthesis Example 1-1, and methyl 5-bromo-2- instead of methyl 2-bromobenzoate used in Synthesis Example 1-2. Iobenzobenzoate was used, and instead of 1-bromo-3-fluorobenzene used in Synthesis Example 1-3, 1-bromo-4-fluorobenzene was used, and the bromine of Synthesis Example 1-5 was used. Omiting the mining process, instead of the diphenylamine used in Synthesis Example 1-6, 4- (tertiary-butyl) -N- (4- (trimethylsilyl) phenyl) prepared in Synthesis Example 8-1 Using the same method as in Synthesis Example 1, except that aniline was used, 4.6 g (yield 39%) of formula H19 was obtained as a pale yellow solid.

MS (MALDI-TOF): m / z 750 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ: 3, 31.3, 34.2, 61.2, 116, 120.7, 121, 122, 122.1, 122.4, 124.8, 125.6, 126.8, 127.6, 128.1, 128.4, 128.6, 129.8, 130.2, 130.4, 131, 131.2, 133, 133.9, 134.5, 135.4, 140.3, 142.8, 143.3, 145.7, 146.3, 160.4 [52C]

Synthesis Example 13. Synthesis of Chemical Formula H25

Synthesis Example 13-1. Synthesis of 4-bromo-2-fluoro-1,1'-biphenyl

<Scheme 8>

Except for using phenylboronic acid instead of the intermediate 1-a used in Synthesis Example 1-2, 4-bromo-2-fluoro-1-iodobenzene instead of methyl 2-bromobenzoate In the same manner, 7 g (yield 70%) of 4-bromo-2-fluoro-1,1'-biphenyl was obtained.

Synthesis Example 13-2. Synthesis of 4-isopropyl-N- (para-tolyl) aniline

Except that 1-bromo-4-methylbenzene was used instead of 1-bromo-4-cyanobenzene used in Synthesis Example 7-1, and 4-isopropylaniline was used instead of 4-cyanoaniline. 11 g (yield 68%) of 4-isopropyl-N- (para-tolyl) aniline was obtained by the method.

Synthesis Example 13-3. Synthesis of Compound H25

Instead of 1-bromo-3-fluorobenzene used in Synthesis Example 1-3, 4-bromo-2-fluoro-1,1'-biphenyl prepared in Synthesis Example 13-1 was used, and A compound which is a light yellow solid using the same method except that 4-isopropyl-N- (para-tolyl) aniline prepared in Synthesis Example 13-2 was used instead of the diphenylamine used in Synthesis Example 1-6. 4.2 g (38% yield) of H25 were obtained.

MS (MALDI-TOF): m / z 1053 [M] ⁺ . ¹³ CNMR (75 MHz, CDCl ₃ ) δ: 21.3, 23.3, 33.2, 62.2, 109, 116.5, 120.7, 121, 122.1, 122.4, 126.6, 127, 127.6, 127.7, 127.9, 128.3, 128.7, 129, 129.2, 129.4, 129.9, 130.7, 131.6, 131.7, 131.8, 134.6, 135.4, 135.6, 136.5, 139.4, 140, 140.3, 142.8, 142.9, 143.1, 143.8, 156.2 [77C]

Example

Device Fabrication and Evaluation: Example  1 to 10

2 mm 크기가 되도록 패터닝한 후 세정하였다. 상기 ITO 글래스를 진공 챔버에 장착한 후 베이스 압력이 1

10^-7torr가 되도록 한 후, 상기 ITO 위에 CuPc(800 Å), α-NPD(300 Å)순으로 성막한 후 하기 [화합물 141] 95 wt%과 상기 합성예 1 내지 10에서 얻어진 BD1 내지 BD10 중 선택한 하나의 화합물 5 wt% 를 발광층으로서 성막(250 Å)한 다음 Alq₃(350 Å), LiF(5 Å), Al(500 Å)의 순서로 성막하여 유기 전계 발광 소자를 제조하였다. ITO glass emitting area 2 mm

Patterned to 2 mm size and washed. After mounting the ITO glass in the vacuum chamber, the base pressure is 1

10 to ⁷ torr, and then formed into CuPc (800 kPa) and α-NPD (300 kPa) on the ITO, followed by 95 wt% of [Compound 141] and BD1 to BD10 obtained in Synthesis Examples 1 to 10. 5 wt% of one selected compound as a light emitting layer was formed (250 mmW), and then formed in the order of Alq ₃ (350 mmW), LiF (5 mmW), and Al (500 mW) to prepare an organic EL device.

[Compound 141] and [BD1] to [BD10] are as follows.

[Compound 141]

Examples 11-43

An organic electroluminescent device was manufactured in the same manner as in Example 1 to 10 except for using the light emitting layer shown in Table 1 instead of the light emitting layer, and the light emission characteristics of the organic light emitting device were measured at 0.4 mA.

Herein, the structures of Compound 79, Compound 105, and Compound 129 used in Table 1 are as follows.

[Chemistry 79] [Chemistry 105] [Compound 129]

Comparative example  1 to 11

An organic electroluminescent device was manufactured in the same manner as in Example 1 to 10 except for using the light emitting layer shown in Table 1 instead of the light emitting layer used in Examples 1 to 10, and among the compounds shown in Table 1 below, The structure is as follows:

[DH1] [DH2] [DH3]

[DD1] [DD2]

Evaluation Examples 1 to 43 and Comparative Evaluation Examples 1 to 11

For organic light emitting devices manufactured according to Examples 1 to 43 and Comparative Examples 1 to 11, driving voltage, current, luminance (measured at 0.4 mA), quantum efficiency, and color coordinates were measured, and the results are shown in Table 1 below. Indicated.

anthracene
derivative Arylamine
derivative Voltage
(V) Current density
(㎃ / ㎠) Luminance
(Cd / ㎡) quantum
efficiency CIEx CIEy Example 1 Compound141 BD1 3.7 10 860 7.5 0.14 0.13 Example 2 Compound141 BD2 3.6 10 840 7.3 0.14 0.14 Example 3 Compound141 BD3 3.7 10 910 8.3 0.14 0.12 Example 4 Compound141 BD4 3.6 10 870 7.2 0.14 0.13 Example 5 Compound141 BD5 3.7 10 850 7.3 0.14 0.13 Example 6 Compound141 BD6 3.7 10 830 7.3 0.14 0.13 Example 7 Compound141 BD7 3.6 10 900 7.5 0.14 0.12 Example 8 Compound141 BD8 3.7 10 910 7.7 0.14 0.13 Example 9 Compound141 BD9 3.7 10 840 7.2 0.14 0.14 Example 10 Compound141 BD10 3.7 10 840 7.1 0.14 0.13 Comparative Example 1 Compound141 DD1 3.6 10 730 5.6 0.14 0.14 Comparative Example 2 Compound141 DD2 3.6 10 510 5.9 0.14 0.14 Comparative Example 3 DH1 BD1 3.7 10 200 6.0 0.14 0.13 Comparative Example 4 DH2 BD1 3.7 10 320 5.7 0.14 0.14 Comparative Example 5 DH3 BD1 3.7 10 280 4.0 0.14 0.14 Example 11 Compound79 BD1 3.6 10 880 8.1 0.14 0.13 Example 12 Compound79 BD2 3.6 10 850 7.9 0.14 0.14 Example 13 Compound79 BD3 3.7 10 900 8.8 0.14 0.12 Example 14 Compound79 BD4 3.7 10 880 7.6 0.14 0.13 Example 15 Compound79 BD5 3.7 10 870 7.5 0.14 0.13 Example 16 Compound79 BD6 3.6 10 860 7.7 0.14 0.13 Example 17 Compound79 BD7 3.7 10 930 7.5 0.14 0.12 Example 18 Compound79 BD8 3.6 10 960 9.1 0.14 0.13 Example 19 Compound79 BD9 3.6 10 850 7.5 0.14 0.14 Example 20 Compound79 BD10 3.6 10 850 7.4 0.14 0.13 Comparative Example 6 Compound79 DD1 3.6 10 740 5.9 0.14 0.14 Comparative Example 7 Compound79 DD2 3.7 10 530 6.0 0.14 0.14 Example 21 Compound 105 BD1 3.7 10 890 8.3 0.14 0.13 Example 22 Compound 105 BD2 3.6 10 860 8.0 0.14 0.14 Example 23 Compound 105 BD3 3.7 10 920 8.4 0.14 0.12 Example 24 Compound 105 BD4 3.7 10 900 7.7 0.14 0.13 Example 25 Compound 105 BD5 3.7 10 890 7.4 0.14 0.13 Example 26 Compound 105 BD6 3.7 10 840 7.8 0.14 0.13 Example 27 Compound 105 BD7 3.7 10 930 7.4 0.14 0.12 Example 28 Compound 105 BD8 3.7 10 980 8.9 0.14 0.13 Example 29 Compound 105 BD9 3.7 10 860 7.4 0.14 0.14 Example 30 Compound 105 BD10 3.7 10 840 7.5 0.14 0.13 Comparative Example 8 Compound 105 DD1 3.6 10 730 6.6 0.14 0.14 Comparative Example 9 Compound 105 DD2 3.6 10 540 6.4 0.14 0.14 Example 31 Compound129 BD1 3.7 10 840 8.0 0.14 0.14 Example 32 Compound129 BD2 3.6 10 820 7.9 0.14 0.12 Example 33 Compound129 BD3 3.7 10 890 8.7 0.14 0.13 Example 34 Compound129 BD4 3.6 10 870 7.7 0.14 0.13 Example 35 Compound129 BD5 3.6 10 890 7.6 0.14 0.13 Example 36 Compound129 BD6 3.6 10 850 7.5 0.14 0.13 Example 37 Compound129 BD7 3.7 10 910 7.5 0.14 0.12 Example 38 Compound129 BD8 3.7 10 930 8.6 0.14 0.13 Example 39 Compound129 BD9 3.7 10 830 7.7 0.14 0.13 Example 40 Compound129 BD10 3.7 10 820 7.8 0.14 0.13 Example 41 Compound79 Formula H3 3.6 10 920 9.0 0.14 0.13 Example 42 Compound79 Chemical Formula H19 3.6 10 870 8.5 0.14 0.13 Example 43 Compound79 Chemical Formula H25 3.7 10 900 8.8 0.14 0.14 Comparative Example 10 Compound129 DD1 3.7 10 750 6.0 0.14 0.13 Comparative Example 11 Compound129 DD2 3.6 10 540 6.0 0.14 0.13

From Table 1, the organic light emitting element of Examples 1 to 43 can confirm the characteristic which has the outstanding efficiency, brightness | luminance, and color purity compared with the organic light emitting element of Comparative Examples 1-11.

2 is a light emission spectrum of the organic light emitting device obtained in Example 21 and Comparative Example 8. FIG. This result is consistent with the increase in efficiency since the size of the emission spectrum of the embodiment is larger than that of the comparative example.

Claims (13)

An aromatic amine derivative represented by the following [formula A].
[Formula A]

In [Formula A],
Ar ₁ and Ar ₂ are the same as or different from each other, and each independently, an aryl group having 6 to 20 carbon atoms substituted with a fluorine or cyano group or a halogenated alkyl group; Or a heteroaryl group having 3 to 20 carbon atoms including a nitrogen atom in an aromatic ring,
Ar ₁ and Ar ₂ may be bonded to each other to form a ring;
X ₁ to X ₈ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon number 6 to An aryl group of 50, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having 0, N or S as a hetero atom, a nitrile group, a nitro group, a halogen group, and a group adjacent to each other and an aliphatic group, May form a condensed ring of an aromatic or aromatic hetero;
One or two of X ₁ to X ₈ is a substituent represented by the structural formula Y1.
[Structure Formula Y1]

In the above Y1,
'*' Means a binding site capable of binding to Formula A at X ₁ to X ₈ ,
L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a single bond,
m is an integer from 0 to 2, and when m is 2, each L is the same or different,
A and B are each a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms, and may form a condensed ring of an aliphatic, aromatic or aromatic hetero group with adjacent groups. Can be. The method of claim 1,
X ₁ to X ₈ in [Formula A] are the same or different and independently from each other, hydrogen; heavy hydrogen; Halogen atom; Cyano group; Nitro group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituent of Formulas 4A, 4E, and 4F; Wherein one or two of X ₁ to X ₈ are substituents represented by the structural formula Y1:

In Chemical Formulas 4A, 4E, and 4F,
Z ₁ to Z ₇ are each independently hydrogen; heavy hydrogen; Halogen atom; Cyano group; Nitro group; An alkyl group having 1 to 10 carbon atoms; An alkyl group having 1 to 10 carbon atoms substituted with one or more of deuterium, a halogen atom, a cyano group, and a nitro group; Phenyl group; Naphthyl group; Fluorenyl group; Phenanthrenyl group; Anthryl group; Pyrenyl group; Chrysenyl group; Selected from deuterium, halogen atom, cyano group, nitro group, phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthryl group, pyrenyl group and chrysenyl group substituted with one or more of alkyl groups having 1 to 10 carbon atoms Is either. The method of claim 2,
_One of X ₁ to X ₄ and one of X ₅ to X ₈ in Formula A is an aromatic amine derivative, characterized in that the substituent represented by the structural formula Y1. The method of claim 3, wherein
The compound of formula A is an aromatic amine derivative, characterized in that represented by any one selected from formulas 1A-1 to 1G-4.
[Formula 1A-1] [Formula 1A-2] [Formula 1A-3]

[Formula 1A-4] [Formula 1A-5] [Formula 1A-6]

[Formula 1B-1] [Formula 1B-2] [Formula 1C-1]

[Formula 1C-2] [Formula 1C-3] [Formula 1D-1]

[Formula 1D-2] [Formula 1D-3] [Formula 1D-4]

[Formula 1D-5] [Formula 1D-6] [Formula 1E-1]

[Formula 1E-2] [Formula 1E-3] [Formula 1E-4]

[Formula 1E-5] [Formula 1F-1] [Formula 1F-2]

[Formula 1F-3] [Formula 1F-4] [Formula 1G-1]

[Formula 1G-2] [Formula 1G-3] [Formula 1G-4]

Ar ₁ to Ar ₄ are the same substituents as Ar ₁ and Ar ₂ defined in Chemical Formula A in claim ₁ ,
X ₁ to X ₂₄ are the same substituents as X ₁ to X ₈ defined in Chemical Formula A in claim ₁ ;
[Formula 1A-1] to [Formula 1A-6] and [Formula 1B-1] to [Formula 1B-2] in _one of X ₁ to X ₄ and one of X ₅ to X ₁₂ is the structural formula Y1. ; [Chemical Formula 1C-1] to [Chemical Formula 1C-3], _one of X ₁ to X ₄ and one of X ₅ to X ₁₀ is the structural formula Y1; In Formula 1D-1 to Formula 1D-6, _one of X ₁ to X ₆ and one of X ₇ to X ₁₂ is the structural formula Y1; In Formula 1E-1, one of X ₁ to X ₄ and one of X ₆ to X ₉ are the structural formula Y1; In Formula 1E-2 to Formula 1E-3, _one of X ₁ to X ₄ and one of X ₇ to X ₁₀ is the structural formula Y1;
In Formula 1E-4, _one of X ₁ to X ₆ and one of X ₈ to X ₁₁ are the structural formula Y1; In Formula 1E-5, _one of X ₁ to X ₆ and one of X ₉ to X ₁₂ are the structural formula Y1; In Formula 1F-1 to Formula 1F-2, _one of X ₁ to X ₄ and one of X ₅ to X ₁₂ is the structural formula Y1; [Formula 1F-3] to [Formula 1F-4] and [Formula 1G-1] to [Formula 1G-3] in _one of X ₁ to X ₄ and one of X ₅ to X ₁₄ is the structural formula Y1. ; In Formula 1G-4, _one of X ₁ to X ₄ and one of X ₅ to X ₂₄ are the structural formula Y1. The method of claim 4, wherein
Ar ₁ to Ar ₄ of Formula (A) is an aromatic amine derivative, characterized in that any one selected from substituents A1 to A45.
[A substituent A1] [A substituent A2] [A substituent A3]

[4 substituent] [5 substituent] [6 substituent]

[Substitution 7] [Substitution 8] [Substitution 9]

[Substitution 10] [Substitution 11] [Substitution 12]

[Substitution 13] [Substitution 14] [Substitution 15]

[Substituent 16] [Substituent 17] [Substituent 18]

[Substitution 19] [Substitution 20] [Substitution 21]

[A substituent A22] [A substituent A23] [A substituent A24]

[A substituent A25] [A substituent A26] [A substituent A27]

[A substituent A28] [A substituent A29] [A substituent A30]

[A substituent A31] [A substituent A32] [A substituent A33]

[Substituent 34] [substituent 35] [substituent 36]

[Substituent A37] [Substituent A38] [Substituent A39]

[A substituent A40] [A substituent A41] [A substituent A42]

[A substituent A43] [A substituent A44] [A substituent A45]

'*' In the substituents A1 to A45 means a binding site bonded to a position of Ar ₁ to Ar ₄ in Formula A. The method of claim 3, wherein
Formula A is an aromatic amine derivative, characterized in that it comprises only two substituents of the formula Y1. The method of claim 1,
Substituent A and substituent B of Structural Formula Y1 are each one selected from substituents B1 to B46 below.
[Substituent B1] [substituent B2] [substituent B3]

[Substituent B4] [substituent B5] [substituent B6]

[Substituent B7] [Substituent B8] [Substituent B9]

[Substituent B10] [Substituent B11] [Substituent B12]

[Substituent B13] [Substituent B14] [Substituent B15]

[Substituent B16] [Substituent B17] [Substituent B18]

[Substituent B19] [Substituent B20] [Substituent B21]

[Substituent B22] [Substituent B23] [Substituent B24]

[Substituent B25] [Substituent B26] [Substituent B27]

[Substituent B28] [Substituent B29] [Substituent B30]

[Substituent B31] [Substituent B32] [Substituent B33]

[Substituent B34] [Substituent B35] [Substituent B36]

[Substituent B37] [Substituent B38] [Substituent B39]

[Substituent B40] [Substituent B41] [Substituent B42]

[Substituent B43] [Substituent B44] [Substituent B45]

[Substituent B46]

In the substituents B1 to B46, R is the same or different and independently from each other, hydrogen, deuterium, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon number 3 to It may be selected from a 60 cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms. And
n is an integer from 0 to 12, and each substituent may be fused with a group adjacent to each other to form a ring. The method of claim 1,
[Formula A] is an aromatic amine derivative, characterized in that any one selected from the group represented by the following formula H1 to formula H46.
'-D' in the formula (H11) herein means that the hydrogen site of the aromatic ring is substituted with deuterium.
[Formula H1] [Formula H2] [Formula H3]

[Formula H4] [Formula H5] [Formula H6]

[Formula H7] [Formula H8] [Formula H9]

[Formula H10] [Formula H11] [Formula H12]

[Formula H13] [Formula H14] [Formula H15]

[Formula H16] [Formula H17] [Formula H18]

Formula H19 Formula H20 Formula H21

[Formula H22] [Formula H23] [Formula H24]

[Formula H25] [Formula H26] [Formula H27]

Formula H28 Formula H29 Formula H30

[Formula H31] [Formula H32] [Formula H33]

[Formula H34] [Formula H35] [Formula H36]

[Formula H37] [Formula H38] [Formula H39]

[Formula H40] [Formula H41] [Formula H42]

[Formula H43] [Formula H44] [Formula H45]

[Formula H46]

A first electrode;
A second electrode opposed to the first electrode; And
And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one compound of any one selected from claims 1 to 8. The method of claim 9,
And the organic layer comprises at least one of a hole injection layer, a hole transport layer, a hole injection function, and a hole injection function and at least one of a functional layer, a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 9,
The organic light emitting device of claim 1, wherein the organic layer interposed between the first electrode and the second electrode is a light emitting layer. The method of claim 11,
The light emitting layer includes a host and a dopant, and the aromatic amine derivative is used as a dopant. The method of claim 12,
The host is an organic light emitting device, characterized in that the compound represented by the formula (B).
[Formula B]

Ar _7, Ar ₈ and Ar ₉ are the same as or different from each other, and each independently, a single bond, a substituted or unsubstituted C ₅ -C ₆₀ aromatic linking group, or a substituted or unsubstituted C ₂ -C ₆₀ heteroaromatic linking group;
R ₂₁ to R ₃₀ are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted C 1 to 60 alkyl group, a substituted or unsubstituted C 3 to 60 It may be selected from a cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, ,
E, f and g are the same as or different from each other, and each independently an integer of 0 to 4;
The two sites represented by '*' of the anthracene may be the same or different from each other, and may independently combine with the P or Q structure to constitute an anthracene-based derivative selected from Formulas 1Aa-1 to 1Aa-3. .
[Formula 1Aa-1] [Formula 1Aa-2] [Formula 1Aa-3]

Here, the 'substituted' in the 'substituted or unsubstituted' is deuterium, cyano group, halogen group, nitro group, alkyl group of 1 to 24 carbon atoms, halogenated alkyl group of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms Group, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 1 to 24 carbon atoms It means to be substituted with one or more substituents.

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