KR20220000442A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound capable of improving luminous efficiency, stability and lifespan of an element, an organic electric element using the same, and an electronic device thereof. The present invention provides a compound represented by chemical formula (1). By using the compound according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the element can be achieved, and color purity and lifespan of the element can be greatly improved.

Description

A compound for an organic electric device, an organic electric device using the same, and an electronic device thereof

The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, 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 electric device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

A material used as an organic layer in an organic electric 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, etc. according to their function.

Lifespan and efficiency are the most problematic for organic light emitting diodes, and as displays become larger, these problems of efficiency and lifespan must be resolved. Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan.

However, the efficiency cannot be maximized by simply improving the organic material layer. This is because, when the energy level and T1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time.

In addition, in order to solve the light emitting problem in the hole transport layer in recent organic electroluminescent devices, a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer. It is time for layer development.

In general, electrons are transferred from the electron transport layer to the emission layer, and holes are transferred from the hole transport layer to the emission layer, and excitons are generated by recombination.

However, most materials used for the hole transport layer have a low T1 value because they have to have a low HOMO value. As a result, excitons generated in the emission layer are transferred to the hole transport layer, resulting in charge unbalance in the emission layer. This results in light emission at the hole transport layer interface.

When light is emitted at the hole transport layer interface, the color purity and efficiency of the organic electric device are lowered and the lifespan is shortened. Therefore, it is urgently required to develop a light emitting auxiliary layer having a high T1 value and having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer.

On the other hand, while delaying the penetration and diffusion of metal oxide from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifespan of the organic electric device, stable characteristics against Joule heating generated during device driving, that is, high glass transition There is a need for development of a hole injection layer material having a temperature. The low glass transition temperature of the hole transport layer material has a characteristic of lowering the uniformity of the thin film surface when driving the device, which is reported to have a significant effect on the device lifespan. In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance.

That is, in order to sufficiently exhibit the excellent characteristics of the organic electric device, the material constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc. is stable and efficient. Supported by materials should be preceded, but the development of stable and efficient organic layer materials for organic electric devices has not yet been sufficiently developed. Accordingly, the development of new materials continues to be demanded.

KR 1020130076842 A

In order to solve the problems of the above-mentioned background art, the present invention has revealed a compound having a novel structure, and the fact that when this compound is applied to an organic electric device, the luminous efficiency, stability and lifespan of the device can be greatly improved revealed

Accordingly, an object of the present invention is to provide a novel compound, an organic electric device using the same, and an electronic device thereof.

The present invention provides a compound represented by the following formula (1).

Formula (1)

In another aspect, the present invention provides an organic electric device comprising the compound represented by the formula (1) and an electronic device thereof.

By using the compound according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the device can be achieved, and color purity and lifespan of the device can be greatly improved.

1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
4 shows a chemical formula according to an aspect of the present invention.

Hereinafter, it will be described in detail with reference to embodiments of the present invention. In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, in describing the components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the elements from other elements, and the essence, order, or order of the elements are not limited by the terms. When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is between each component. It should be understood that elements may also be “connected,” “coupled,” or “connected.”

As used in this specification and the appended claims, unless otherwise indicated, the following terms have the following meanings:

As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise specified.

The term "alkyl" or "alkyl group" as used herein, unless otherwise specified, has a single bond of 1 to 60 carbon atoms, a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cyclo means a radical of saturated aliphatic functional groups including alkyl groups and cycloalkyl-substituted alkyl groups.

As used herein, the terms "alkenyl group", "alkenyl group" or "alkynyl group" have a double or triple bond of 2 to 60 carbon atoms, respectively, unless otherwise specified, and include a straight or branched chain group, , but not limited thereto.

As used herein, the term “cycloalkyl” refers to an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, and is not limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has 1 to 60 carbon atoms unless otherwise specified, and is limited thereto. it is not

As used herein, the term “aryloxyl group” or “aryloxy group” refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, and are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by a neighboring substituent joining or participating in a reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the number of carbon atoms described herein.

Also, when prefixes are named consecutively, it is meant that the substituents are listed in the order listed first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group and wherein the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heterocyclic group" used in the present invention, unless otherwise specified, contains one or more heteroatoms, has 2 to 60 carbon atoms, includes at least one of a single ring and multiple rings, and includes a heteroaliphatic ring and a hetero aromatic rings. It may be formed by combining adjacent functional groups.

As used herein, the term “heteroatom” refers to N, O, S, P or Si, unless otherwise specified.

In addition, the "heterocyclic group" may include a ring containing _{SO 2 instead of carbon forming the ring.} For example, "heterocyclic group" includes the following compounds.

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structures, respectively, unless otherwise specified, " A substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to It includes the case of forming a compound as a spy together.

The term "spiro compound" used in the present invention has a 'spiro union', and the spiro linkage means a connection formed by sharing only one atom in two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and they are respectively 'monospiro-', 'dispiro-', 'trispiro-', depending on the number of spiro atoms in a compound. ' It's called a compound.

Unless otherwise specified, as used herein, the term "aliphatic" refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocycle having 2 to 60 carbon atoms, or a combination thereof, It contains saturated or unsaturated rings.

Other heterocompounds or heteroradicals other than the above-mentioned heterocompounds include one or more heteroatoms, but are not limited thereto.

In addition, unless otherwise explicitly stated, in the term "substituted or unsubstituted" used in the present invention, "substitution" means deuterium, halogen, amino group, nitrile group, nitro group, C ₁ ~ C ₂₀ alkyl group, C ₁ ~ C ₂₀ alkoxy group, C ₁ ~ C ₂₀ alkyl amine group, C ₁ ~ C ₂₀ alkyl thiophene group, C ₆ ~ C ₂₀ aryl thiophene group, C ₂ ~ C ₂₀ alkenyl group, C ₂ ~ C of ₂₀ alkynyl, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, of a C ₆ ~ C ₂₀ substituted by deuterium aryl group, a C ₈ ~ C ₂₀ aryl alkenyl group, a silane group, a boron It means substituted with one or more substituents selected from the group consisting of a group, a germanium group, and a C ₂ ~ C _{20 heterocyclic group, but is not limited to these substituents.}

In addition, unless there is an explicit explanation, the formula used in the present invention is applied in the same way as the definition of the substituent by the exponent definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3 Each is bonded as follows, where R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the hydrogen bonded to the carbon forming the benzene ring is omitted.

As used herein, the term "non-existent" means that there is no association unless otherwise specified.

Hereinafter, a compound according to an aspect of the present invention and an organic electric device including the same will be described.

The present invention provides a compound represented by the following formula (1).

Formula (1)

In the formula (1), each symbol may be defined as follows.

1) X, Y and Z are independently of each other O, S, NR', CR'R" or absent;

2) R′ and R″ are each independently hydrogen; deuterium; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₂ ~ C ₆₀ alkynyl group; C ₁ ~ C ₆₀ alkoxy group; C ₆ ~ C ₆₀ Aryloxy group; C ₆ ~ C _{60 Aryl group; Fluorenyl group; C 2} ~ C ₆₀ Heterocyclic group containing at least one heteroatom of O, N, S, Si and P and a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group;

When R′ and R″ are an alkyl group, it may be preferably a C ₁ to C ₃₀ alkyl group, and more preferably a C ₁ to C ₂₄ alkyl group.

When R′ and R″ are alkenyl groups, they may be preferably C ₂ to C ₃₀ alkenyl groups, and more preferably C ₂ to C ₂₄ alkenyl groups.

When R' and R" are an alkynyl group, it may be preferably a C ₂ ~ C ₃₀ alkynyl group, and more preferably a C ₂ ~ C ₂₄ alkynyl group.

When R′ and R″ are an alkoxyl group, it may be preferably a C ₁ to C ₃₀ alkoxyl group, and more preferably a C ₁ to C ₂₄ alkoxyl group.

When R' and R" are an aryloxy group, it may be preferably a C ₆ ~ C ₃₀ aryloxy group, and more preferably a C ₆ ~ C ₂₄ aryloxy group.

When R' and R" are aryl groups, they may be preferably a _{C 6} -C _{30 aryl group, more preferably a C 6} -C ₂₄ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

When R' and R" are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, Pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuro pyrimidine, phenothiazine, phenylphenothiazine, and the like.

When R' and R" are a fused cyclic group, preferably a C ₃ ~ C ₃₀ aliphatic ring and a C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably a C ₃ ~ C ₂₄ aliphatic ring and C _It may be a fused ring group of an aromatic ring of 6 ~ C _{24 .}

3) Ar is a C ₆ ~ C ₆₀ aryl group; Or O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group;

When Ar is an aryl group, it may be preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₂₄ aryl group, such as phenylene, biphenyl, naphthalene, terphenyl, and the like.

When Ar is a heterocyclic group, it is preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, pheno thiazine, phenylphenothiazine, and the like.

4) R ¹ , R ² , R ³ and R ⁴ are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ Alkenyl group; C ₂ ~ C ₆₀ Alkynyl group; C ₁ ~ C ₆₀ Alkoxy group; C ₆ ~ C ₆₀ Aryloxy group; And -L'-NR ^a R ^b; is selected from the group consisting of, or adjacent a plurality of R ¹ each other, or a plurality of R ² to each other, or a plurality of R ³ to each other, or a plurality of R ⁴ ring by combining to each other, can form.

When R ¹ , R ² , R ³ and R ⁴ are an aryl group, it is preferably a _{C 6} ~ C _{30 aryl group, most preferably a C 6} ~ C ₂₅ aryl group, for example, phenyl, biphenyl , naphthyl, phenanthrene, terphenyl, and the like.

When R ¹ , R ² , R ³ and R ⁴ are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine , thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothieno pyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When R ¹ , R ² , R ³ and R ⁴ are a fused ring group, preferably a C ₃ ~ C ₃₀ aliphatic ring and a C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably C ₃ ~ C _It may be a fused ring group of a ₂₄ aliphatic ring and a C ₆ ~ C 24 aromatic ring.

When R ¹ , R ² , R ³ and R ⁴ are an alkyl group, it may be preferably a C ₁ to C ₃₀ alkyl group, and more preferably a C ₁ to C ₂₄ alkyl group.

When R ¹ , R ² , R ^{3 ,} and R ⁴ are alkenyl groups, they may be preferably C ₂ to C ₃₀ alkenyl groups, and more preferably C ₂ to C ₂₄ alkenyl groups.

When R ¹ , R ² , R ³ and R ⁴ are an alkynyl group, it may be preferably a C ₂ ~ C ₃₀ alkynyl group, and more preferably a C ₂ ~ C ₂₄ alkynyl group.

When R ¹ , R ² , R ³ and R ⁴ are an alkoxyl group, it may be preferably a C ₁ to C ₃₀ alkoxyl group, and more preferably a C ₁ to C ₂₄ alkoxyl group.

When R ¹ , R ² , R ³ and R ⁴ are an aryloxy group, it may be preferably a C ₆ ~ C ₃₀ aryloxy group, and more preferably a C ₆ ~ C ₂₄ aryloxy group.

5) L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ An aliphatic ring group; selected from the group consisting of, wherein R ^a and R ^b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; and a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring fused ring group; is selected from the group consisting of.

When L' is an arylene group, it may be preferably a C ₆ ~ C ₃₀ arylene group, more preferably a C ₆ ~ C ₂₄ arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc. have.

When L' is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole , 5-phenyl-5H-pyrimido [5,4-b] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, It may be phenothiazine, phenylphenothiazine, and the like.

When L' is an aliphatic cyclic group, it may be preferably a C ₃ to C ₃₀ aliphatic group, more preferably a C ₃ to C ₂₄ aliphatic group.

When R ^a and R ^b are an aryl group, it is preferably a _{C 6} ~ C _{30 aryl group, most preferably a C 6} ~ C ₂₅ aryl group, for example, phenyl, biphenyl, naphthyl, phenanthrene , terphenyl, and the like.

When R ^a and R ^b are a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, Pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuro pyrimidine, phenothiazine, phenylphenothiazine, and the like.

When R ^a and R ^b are a fused cyclic group, preferably a C ₃ ~ C ₃₀ aliphatic ring and a C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably a C ₃ ~ C ₂₄ aliphatic ring and C _It may be a fused ring group of an aromatic ring of 6 ~ C _{24 .}

6) a is an integer from 0 to 4, b and d are each independently an integer from 0 to 3, and c is an integer from 0 to 2.

Here, the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ Alkoxy group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₆ ~ C ₂₀ Aryl group; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; C ₇ ~ C ₂₀ Arylalkyl group; C ₈ ~ C ₂₀ Aryl alkenyl group; and -L'-NR ^a R ^b ; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' means C ₃ ~ C ₆₀ An aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring or C ₂ ~ C ₆₀ heterocyclic ring or a fused ring consisting of a combination thereof, including a saturated or unsaturated ring.

In addition, the present invention provides a compound wherein the formula (1) is represented by any one of the following formulas (2) to (6).

Formula (2) Formula (3)

Chemical formula (4) Chemical formula (5) Chemical formula (6)

{In the above formulas (2) to (6),

1) X, Z, Ar, R ¹ , R ² , R ³ , R ⁴ , R', R", a and b are the same as defined in Formula (1) above,

2) c is an integer from 0 to 2, d and c' are independently integers from 0 to 3, and d' is an integer from 0 to 4.}

In addition, the present invention provides a compound wherein the formula (1) is represented by any one of the following formulas (7) to (11).

Formula (7) Formula (8)

Chemical formula (9) Chemical formula (10) Chemical formula (11)

{In the above formulas (7) to (11),

1) X, Y, Ar, R ¹ , R ² , R ³ , R ⁴ , R′, R″, a and d are the same as defined in Formula (1) above,

2) b and c' are each independently an integer from 0 to 3, c is an integer from 0 to 2, and b' is an integer from 0 to 4.}

In addition, the present invention provides a compound in which Ar of the above formula (1) is represented by the following formula (A).

Formula (A)

{In the formula (A),

1) A and B are each independently a C ₆ ~ C ₂₀ aryl group; Or C ₄ ~ C ₂₀ A heterocyclic group; and

2) V ¹ and V ² are each independently a single bond, O, S, NR' or CR'R", with the proviso that V ¹ and V ² are both single bonds, except when they are single bonds;

3) R′ and R″ are the same as defined in Formula (1),

4) The tilde indicates the bonding position.}

In addition, the present invention provides a compound in ^{which at least one of R 1} to R ⁴ in Formula (1) is represented by the following Formula (B) or Formula (C).

In the above formula (B) or formula (C), each symbol may be defined as follows.

1) L ¹ and L ² are the same as the definition of L' in Formula (1),

2) Ar ¹ and Ar ² are the same as defined ^{for R a} in Formula (1),

3) X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently CRx or N, provided that at least one of ^{X 1} , X ² , X ³ , X ⁴ and X ^{5 is N,}

4) wherein Rx is hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; fluorenyl group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ Alkenyl group; C ₂ ~ C ₆₀ Alkynyl group; C ₁ ~ C ₆₀ An alkoxyl group; And C ₆ ~ C ₆₀ Aryloxy group; is selected from the group consisting of.

When Rx is an aryl group, it is preferably a _{C 6} ~ C _{30 aryl group, most preferably a C 6} ~ C ₂₄ aryl group, for example, phenyl, biphenyl, naphthyl, phenanthrene, terphenyl, etc. can

When Rx is a heterocyclic group, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₄ heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran, benzothienopyrimidine, benzofuropyrimidine, pheno thiazine, phenylphenothiazine, and the like.

When Rx is a fused ring group, preferably a C ₃ ~ C ₃₀ aliphatic ring and a C ₆ ~ C ₃₀ aromatic ring fused ring group, more preferably a C ₃ ~ C ₂₄ aliphatic ring and C ₆ ~ C ₂₄ It may be a fused ring group of an aromatic ring of

When Rx is an alkyl group, it may be preferably a C ₁ to C ₃₀ alkyl group, and more preferably a C ₁ to C ₂₄ alkyl group.

When Rx is an alkenyl group, it may be preferably a C ₂ -C ₃₀ alkenyl group, and more preferably a C ₂ -C ₂₄ alkenyl group.

When Rx is an alkynyl group, it may be preferably a C ₂ ~ C ₃₀ alkynyl group, more preferably a C ₂ ~ C ₂₄ alkynyl group.

When Rx is an alkoxyl group, it may be preferably a C ₁ to C ₃₀ alkoxyl group, and more preferably a C ₁ to C ₂₄ alkoxyl group.

When Rx is an aryloxy group, it may be preferably a C ₆ ~ C ₃₀ aryloxy group, and more preferably a C ₆ ~ C ₂₄ aryloxy group.

5) The tilde indicates the bonding position.

In addition, the present invention provides a compound in which the compound represented by the above formula (1) is represented by any one of the following compounds P-1 to P-120.

1, the organic electric device 100 according to the present invention has a first electrode 110, a second electrode 170, and between the first electrode 110 and the second electrode 170, the chemical formula ( An organic material layer including a single compound represented by 1) or two or more types of compounds is provided. In this case, the first electrode 110 may be an anode or an anode, and the second electrode 170 may be a cathode or a cathode. In the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 on the first electrode 110 . In this case, the remaining layers except for the light emitting layer 140 may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 220 , a buffer layer 210 , and the like, and the electron transport layer 150 and the like may serve as a hole blocking layer. (See Fig. 2)

In addition, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer 180 . The light efficiency improving layer may be formed on a surface of both surfaces of the first electrode that does not contact the organic material layer or on a surface of both surfaces of the second electrode that does not contact the organic material layer. The compound according to an embodiment of the present invention applied to the organic material layer is a hole injection layer 120, a hole transport layer 130, a light emitting auxiliary layer 220, an electron transport auxiliary layer, an electron transport layer 150, an electron injection layer ( 160), a host or dopant of the light emitting layer 140, or a material of the light efficiency improving layer. Preferably, for example, the compound according to formula (1) of the present invention can be used as a material for a hole transport layer or a light emitting layer.

The organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks. (See FIG. 3 . )

On the other hand, even with the same core, the band gap, electrical properties, interface properties, etc. may vary depending on which position of the substituent is bonded to the same core, so the selection of the core and the combination of the sub-substituents coupled thereto are also very In particular, when the energy level and T1 value between each organic material layer, and the intrinsic properties (mobility, interfacial properties, etc.) of materials are optimally combined, long lifespan and high efficiency can be achieved at the same time.

The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, an anode is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate, and the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and After forming the organic material layer including the electron injection layer 160, it can be manufactured by depositing a material that can be used as a cathode thereon.

In addition, in the present invention, the organic layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic layer is an electron transporting material containing the compound It provides an organic electric device, characterized in that.

As another specific example, the present invention provides an organic electric device, characterized in that the same or heterogeneous compound of the compound represented by the formula (1) is mixed and used in the organic material layer.

In addition, the present invention provides a hole transport layer composition comprising the compound represented by the formula (1), and provides an organic electric device including the hole transport layer.

In addition, the present invention provides a light emitting layer composition comprising the compound represented by Formula (1), and provides an organic electric device including the light emitting layer.

In addition, the present invention is a display device including the above-described organic electric device; and a controller for driving the display device.

In another aspect, the present invention provides an electronic device characterized in that the organic electroluminescent device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a device for single color or white lighting. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation system, a game machine, various TVs, and various computers.

Hereinafter, the examples of the synthesis of the compound represented by the formula (1) of the present invention and the preparation of the organic electric device of the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples. .

[ Synthesis example One]

The compound (Final product) represented by Formula (1) according to the present invention may be prepared by reacting as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

{In Scheme 1, Hal ¹ is one of Cl, Br, and I.}

I. Synthesis of Sub 1

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto. Q is one of -OH, -SH, -NR'H and -CR'R"OH, Hal ² is one of Cl, Br and I, and Hal ³ is Br or I.

<Scheme 2>

One. Sub1 -One Synthesis example

(1) Synthesis of Inter1-1

2''-chloro-[1,1':2',1''-terphenyl]-2-ol (10.0 g, 35.6 mmol) and 2-bromoaniline (12.3 g, 71.2 mmol), 1,8-diazabicyclo[ 5.4.0] undec-7-ene (DBU) (16.3 g, 106.9 mmol), pyridine (0.57 mL), copper powder (0.29 g, 4.63 mmol), CuI (0.31 g, 1.60 mmol) in a round flask and DMF (212 mL) was added and refluxed for 3 hours. When the reaction is complete, after cooling to room temperature, 3M HCl is added until the precipitation is complete. Thereafter, the precipitate was washed with water and dried to obtain 11.0 g of a product. (Yield 83%)

(2) Synthesis of Sub1-1

After dissolving Inter1-1 (11.0 g, 29.6 mmol) in toluene (590 mL) in a round-bottom flask, Pd ₂ (dba) ₃ (0.81 g, 0.89 mmol), P(t-Bu) ₃ (0.36 g, 1.77) mmol), NaOt-Bu (5.7 g, 59.1 mmol) was added, and the reaction was carried out at 80 °C. When the reaction is completed, _{extraction is performed with CH 2} Cl ₂ and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Thereafter, the resulting organic material was recrystallized by silicagel column to obtain 4.7 g of a product. (Yield 47%)

2. Sub1 -7 Synthesis example

(1) Synthesis of Inter1-7-a

Dissolve 2-bromo-2'-chloro-5-iodo-1,1'-biphenyl (25.0 g, 63.5 mmol) in toluene (320 mL) in a round-bottom flask, diphenylamine (10.4 g, 63.5 mmol), Pd ₂ (dba) ₃ (1.75 g, 1.91 mmol), P(t-Bu) ₃ (0.77 g, 3.81 mmol), and NaOt-Bu (12.2 g, 127.1 mmol) were added, and the reaction was carried out at 50°C. When the reaction is completed, _{extraction is performed with CH 2} Cl ₂ and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Thereafter, the resulting organic material was recrystallized using silicagel column to obtain 22.7 g of a product. (yield 82%)

(2) Synthesis of Inter1-7-b

After dissolving Inter1-7-a (22.7 g, 52.1 mmol) obtained in the above synthesis in toluene (260 mL) in a round-bottom flask, aniline (4.7 g, 52.1 mmol), Pd ₂ (dba) ₃ (1.43 g, 1.56) mmol), P(t-Bu) ₃ (0.63 g, 3.13 mmol), and NaOt-Bu (10.0 g, 104.2 mmol) were added and the reaction was carried out at 70°C. When the reaction is completed, _{extraction is performed with CH 2} Cl ₂ and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Thereafter, the resulting organic material was recrystallized by silicagel column to obtain 14.9 g of a product. (Yield 64%)

(3) Synthesis of Inter1-7-c

After dissolving Inter1-7-b (14.9 g, 33.3 mol) obtained in the above synthesis in DMF (Dimethylformamide) (167 mL) in a round-bottom flask, bis(pinacolato)diboron (9.3 g, 36.7 mol), KOAc (9.8 g) , 100 mol), PdCl ₂ (dppf) (0.73 g, 1.00 mmol) were added and stirred at 120° C. When the reaction is complete, DMF is removed through distillation, _{extracted with CH 2} Cl ₂ and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Then, the resulting organic material was recrystallized by silicagel column to obtain 10.4 g of the product. (yield 58%)

(4) Synthesis of Inter1-7

After dissolving Inter1-7-c (10.4 g, 19.3 mmol) obtained in the above synthesis in THF (Tetrahydrofuran) (97 mL) in a round-bottom flask, 2-bromo-N-(2-chlorophenyl)aniline (5.5 g, 19.3) mmol), K ₂ CO ₃ (8.0 g, 58.0 mmol), Pd(PPh ₃ ) ₄ (13.4 g, 1.16 mmol), water (48 mL) were added and stirred at 80° C. When the reaction is completed, _{extraction is performed with CH 2} Cl ₂ and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Thereafter, the resulting organic material was recrystallized using silicagel column to obtain 8.4 g of a product. (Yield 71%)

(5) Synthesis of Sub1-7

After dissolving Inter1-7 (8.4 g, 22.7 mmol) obtained in the above synthesis in toluene (454 mL) in a round-bottom flask, Pd ₂ (dba) ₃ (0.62 g, 0.68 mmol), P(t-Bu) ₃ ( 0.28 g, 1.36 mmol) and NaOt-Bu (4.4 g, 45.4 mmol) were added, and then the experiment was performed in the same manner as in Sub1-1 to obtain 5.5 g of the product. (Yield 42%)

3. Sub1 -20 Synthesis example

(1) Synthesis of Inter1-20-a

After dissolving 1,9-dibromodibenzo[b,d]furan (12.0 g, 36.8 mmol) in THF (Tetrahydrofuran) (184 mL) in a round-bottom flask, (2-chlorophenyl)boronic acid (5.8 g, 36.8 mmol), After addition of K ₂ CO ₃ (15.3 g, 110 mmol), Pd(PPh ₃ ) ₄ (2.55 g, 2.21 mmol), and water (92 mL), the same procedure as for Inter1-7 was conducted to obtain 10.1 g of the product. . (yield 77%)

(2) Synthesis of Inter1-20-b

After dissolving 2-amino-5-bromobenzenethiol (12.0 g, mmol) in THF (Tetrahydrofuran) (294 mL) in a round-bottom flask, (4-(diphenylamino)phenyl)boronic acid (17.0 g, 58.8 mmol), K ₂ After adding CO ₃ (24.4 g, 176 mmol), Pd(PPh ₃ ) ₄ (4.08 g, 3.53 mmol), and water (147 mL), the same procedure as for Inter1-7 was performed to obtain 18.5 g of a product. (yield 85%)

(3) Synthesis of Inter1-20

Inter1-20-a (10.1 g, 28.2 mmol) obtained in the above synthesis was placed in a round-bottom flask under a nitrogen atmosphere and dissolved in Toluene (28 mL), Inter1-20-b (10.4 g, 28.2 mmol), CuI (1.07 g) , 5.63 mmol), ⁿ Bu ₄ NBr (1.9 g, 5.63 mmol), and NaOH (4.51 g, 113 mmol) were added and refluxed. When the reaction is complete, after cooling to room temperature, NH ₄ Cl and ethyl acetate are added, and the mixture is extracted with brine. Thereafter, the extracted organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was recrystallized by silicagel column to obtain 14.6 g of a product. (yield 81%)

(4) Synthesis of Sub1-20

After dissolving Inter1-20 (14.6 g, 22.7 mmol) obtained in the above synthesis in toluene (454 mL) in a round-bottom flask, Pd ₂ (dba) ₃ (0.62 g, 0.68 mmol), P(t-Bu) ₃ ( 0.28 g, 1.36 mmol) and NaOt-Bu (4.4 g, 45.4 mmol) were added, and the same method as in Sub 1-1 was performed to obtain 7.1 g of the product. (Yield 51%)

4. Sub1 -75 Synthesis example

(1) Synthesis of Inter1-75-a

After dissolving 2-bromo-3-iodophenol (50.0 g, 167 mmol) in THF (Tetrahydrofuran) (840 mL) in a round-bottom flask, (2-chlorophenyl)boronic acid (26.2 g, 167 mmol), K ₂ CO ₃ (69.4 g, 502 mmol), Pd(PPh ₃ ) ₄ (11.6 g, 10.0 mmol), and water (420 mL) were added, and the experiment was performed in the same manner as Inter1-7 above to obtain 34.2 g of the product. (yield 72%)

(2) Synthesis of Inter1-75-b

After dissolving Inter1-75-a (34.2 g, 121 mmol) obtained in the above synthesis in THF (Tetrahydrofuran) (600 mL) in a round-bottom flask, (1-bromonaphthalen-2-yl)boronic acid (30.3 g, 121 mmol) ), K ₂ CO ₃ (50.0 g, 362 mmol), Pd(PPh ₃ ) ₄ (8.36 g, 7.24 mmol), and water (300 mL) were added. got (Yield 68%)

(3) Synthesis of Inter1-75-c

Inter1-75-b (33.4 g, 81.5 mmol) obtained in the above synthesis was mixed with Pd(OAc) ₂ (0.92 g, 4.08 mmol), 3-nitropyridine (0.51 g, 4.08 mmol), BzOOt-Bu (tert-butyl peroxybenzoate) (31.7 g, 163 mmol), C ₆ F ₆ (hexafluorobenzene) (122 mL), and DMI (N,N'-dimethylimidazolidinone) (82 mL) were added and refluxed at 90°C for 3 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, and the mixture was extracted with EA and water. The organic layer _{was dried over MgSO 4} and concentrated, and the resulting organic material was recrystallized by silicagel column to obtain 21.1 g of a product. (Yield 63%)

(4) Synthesis of Inter1-75

Inter1-75-c (21.1 g, 51.7 mmol) obtained in the above synthesis was placed in a round-bottom flask under a nitrogen atmosphere and dissolved in Toluene (52 mL), followed by 4-amino-[1,1'-biphenyl]-3-thiol ( 10.4 g, 51.7 mmol), CuI (1.97 g, 10.3 mmol), ⁿ Bu ₄ NBr (3.4 g, 10.3 ), and NaOH (8.27 g, 207 mmol) were added. g was obtained. (yield 79%)

(5) Synthesis of Sub1-75

After dissolving Inter1-75 (21.5 g, 40.7 mmol) obtained in the above synthesis in toluene (815 mL) in a round-bottom flask, Pd ₂ (dba) ₃ (1.12 g, 1.22 mmol), P(t-Bu) ₃ ( 0.49 g, 2.44 mmol) and NaOt-Bu (7.8 g, 81.4 mmol) were added, and the same method as in Sub1-1 was performed to obtain 8.4 g of a product. (Yield 42%)

5. Sub1 -86 Synthesis example

(1) Synthesis of Inter1-86-a

After dissolving 1-bromo-9-chlorodibenzo[b,d]thiophene (20.0 g, 67.2 mmol) in THF (Tetrahydrofuran) (340 mL) in a round-bottom flask, (2-bromophenyl)boronic acid (13.5 g, 67.2 mmol) ), K ₂ CO ₃ (27.9 g, 202 mmol), Pd(PPh ₃ ) ₄ (4.66 g, 4.03 mmol), water (170 mL) were added and stirred at 80° C. When the reaction is completed, _{extraction is performed with CH 2} Cl ₂ and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Thereafter, the resulting organic material was recrystallized by silicagel column to obtain 18.1 g of a product. (yield 72%)

(2) Synthesis of Inter1-86

Inter1-86-a (18.1 g, 48.5 mmol) with 2-aminophenol (10.6 g, 96.9 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (22.1 g, 145 mmol), Put pyridine (0.78 mL), copper powder (0.40 g, 6.30 mmol), and CuI (0.42 g, 2.18 mmol) in a round flask, add DMF (384 mL), and reflux for 3 hours. When the reaction is complete, after cooling to room temperature, 3M HCl is added until the precipitation is complete. Thereafter, the precipitate was washed with water and dried to obtain 15.8 g of a product. (yield 81%)

(3) Synthesis of Sub1-86

After dissolving Inter1-86 (15.8 g, 39.4 mmol) obtained in the above synthesis in toluene (790 mL) in a round-bottom flask, Pd ₂ (dba) ₃ (1.08 g, 1.18 mmol), P(t-Bu) ₃ ( 0.48 g, 2.36 mmol) and NaOt-Bu (7.6 g, 78.8 mmol) were added, and then the same method as in Sub 1-1 was performed to obtain 7.7 g of the product. (Yield 53%)

On the other hand, the compound belonging to Sub 1 may be a compound as follows, but is not limited thereto.

Table 1 below shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 1.

compound FD-MS compound FD-MS Sub1-1 m/z=335.13 (C ₂₄ H ₁₇ NO=335.41) Sub1-2 m/z=351.11 (C ₂₄ H ₁₇ NS=351.47) Sub1-3 m/z=410.18 (C ₃₀ H ₂₂ N ₂ =410.52) Sub1-4 m/z=361.18 (C ₂₇ H ₂₃ N=361.49) Sub1-5 m/z=654.27 (C ₄₈ H ₃₄ N ₂ O=654.81) Sub1-6 m/z=710.28 (C ₅₁ H ₃₈ N ₂ S=710.94) Sub1-7 m/z=577.25 (C ₄₂ H ₃₁ N ₃ =577.73) Sub1-8 m/z=652.25 (C ₄₅ H ₃₃ FN ₂ O ₂ =652.77) Sub1-9 m/z=589.22 (C ₄₂ H ₂₇ N ₃ O=589.7) Sub1-10 m/z=687.27 (C ₄₈ H ₃₇ N ₃ S=687.91) Sub1-11 m/z=485.19 (C ₃₅ H ₂₃ N ₃ =485.59) Sub1-12 m/z=670.33 (C ₄₆ H ₂₃ D ₁₀ FN ₄ =670.86) Sub1-13 m/z=655.24 (C ₄₅ H ₂₉ N ₅ O=655.76) Sub1-14 m/z=594.21 (C ₄₂ H ₃₀ N ₂ S=594.78) Sub1-15 m/z=440.19 (C ₃₁ H ₂₄ N ₂ O=440.55) Sub1-16 m/z=516.17 (C ₃₆ H ₂₄ N ₂ S=516.66) Sub1-17 m/z=590.2 (C ₄₂ H ₂₆ N ₂ O ₂ =590.68) Sub1-18 m/z=776.23 (C ₅₄ H ₃₆ N ₂ S ₂ =777.02) Sub1-19 m/z=834.31 (C ₆₁ H ₄₂ N ₂ S=835.08) Sub1-20 m/z=608.19 (C ₄₂ H ₂₈ N ₂ OS=608.76) Sub1-21 m/z=697.22 (C ₄₈ H ₃₁ N ₃ OS=697.86) Sub1-22 m/z=549.22 (C ₄₀ H ₂₇ N ₃ =549.68) Sub1-23 m/z=682.21 (C ₄₈ H ₃₀ N ₂ OS=682.84) Sub1-24 m/z=533.13 (C ₃₆ H ₂₃ NS ₂ =533.71) Sub1-25 m/z=692.32 (C ₅₂ H ₄₀ N ₂ =692.91) Sub1-26 m/z=658.2 (C ₄₂ H ₂₈ F ₂ N ₄ S=658.77) Sub1-27 m/z=667.26 (C ₄₈ H ₃₃ N ₃ O=667.81) Sub1-28 m/z=541.22 (C ₄₀ H ₂₈ FN=541.67) Sub1-29 m/z=517.15 (C ₃₆ H ₂₃ NOS=517.65) Sub1-30 m/z=714.18 (C ₄₈ H ₃₀ N ₂ OS ₂ =714.9) Sub1-31 m/z=728.26 (C ₅₂ H ₃₂ N ₄ O=728.86) Sub1-32 m/z=375.16 (C ₂₇ H ₂₁ NO=375.47) Sub1-33 m/z=550.24 (C ₄₁ H ₃₀ N ₂ =550.71) Sub1-34 m/z=752.17 (C ₄₉ H ₂₈ N ₄ OS ₂ =752.91) Sub1-35 m/z=731.26 (C ₅₂ H ₃₃ N ₃ O ₂ =731.86) Sub1-36 m/z=379.07 (C ₂₄ H ₁₃ NO ₂ S=379.43) Sub1-37 m/z=513.18 (C ₃₆ H ₂₃ N ₃ O=513.6) Sub1-38 m/z=588.23 (C ₄₂ H ₂₈ N ₄ =588.71) Sub1-39 m/z=530.15 (C ₃₆ H ₂₂ N ₂ OS=530.65) Sub1-40 m/z=879.24 (C ₆₀ H ₃₇ N ₃ OS ₂ =880.1) Sub1-41 m/z=798.23 (C ₅₆ H ₃₄ N ₂ O ₂ S=798.96) Sub1-42 m/z=454.11 (C ₃₀ H ₁₈ N ₂ OS=454.55) Sub1-43 m/z=678.18 (C ₄₅ H ₃₀ N ₂ OS ₂ =678.87) Sub1-44 m/z=586.15 (C ₃₉ H ₂₆ N ₂ S ₂ =586.77) Sub1-45 m/z=596.25 (C ₄₂ H ₃₂ N ₂ O ₂ =596.73) Sub1-46 m/z=709.19 (C ₄₇ H ₂₇ N ₅ OS=709.83) Sub1-47 m/z=679.19 (C ₄₄ H ₂₁ D ₅ N ₄ S ₂ =679.87) Sub1-48 m/z=744.33 (C ₅₄ H ₄₀ N ₄ =744.94) Sub1-49 m/z=577.06 (C ₃₆ H ₁₉ NOS ₃ =577.73) Sub1-50 m/z=639.18 (C ₄₂ H ₂₆ FN ₃ OS=639.75) Sub1-51 m/z=808.23 (C ₅₃ H ₃₆ N ₄ OS ₂ =809.02) Sub1-52 m/z=625.13 (C ₄₀ H ₂₃ N ₃ OS ₂ =625.76) Sub1-53 m/z=401.21 (C ₃₀ H ₂₇ N=401.55) Sub1-54 m/z=460.19 (C ₃₄ H ₂₄ N ₂ =460.58) Sub1-55 m/z=717.22 (C ₅₁ H ₃₁ N ₃ S=717.89) Sub1-56 m/z=648.17 (C ₄₄ H ₂₈ N ₂ S ₂ =648.84) Sub1-57 m/z=770.33 (C ₅₇ H ₄₂ N ₂ O=770.98) Sub1-58 m/z=715.26 (C ₅₂ H ₃₃ N ₃ O=715.86) Sub1-59 m/z=490.24 (C ₃₆ H ₃₀ N ₂ =490.65) Sub1-60 m/z=685.22 (C ₄₇ H ₃₁ N ₃ OS=685.85) Sub1-61 m/z=906.27 (C ₆₃ H ₄₂ N ₂ OS ₂ =907.16) Sub1-62 m/z=820.36 (C ₆₀ H ₄₄ N ₄ =821.04) Sub1-63 m/z=662.24 (C ₄₉ H ₃₀ N ₂ O=662.79) Sub1-64 m/z=894.18 (C ₆₀ H ₃₄ N ₂ OS ₃ =895.13) Sub1-65 m/z=733.35 (C ₅₄ H ₄₃ N ₃ =733.96) Sub1-66 m/z=492.16 (C ₃₄ H ₂₁ FN ₂ O=492.55) Sub1-67 m/z=698.19 (C ₄₈ H ₃₀ N ₂ S ₂ =698.9) Sub1-68 m/z=698.24 (C ₄₉ H ₃₄ N ₂ OS=698.88) Sub1-69 m/z=758.28 (C ₅₅ H ₃₈ N ₂ S=758.98) Sub1-70 m/z=740.23 (C ₅₁ H ₃₆ N ₂ S ₂ =740.98) Sub1-71 m/z=589.22 (C ₄₂ H ₂₇ N ₃ O=589.7) Sub1-72 m/z=761.22 (C ₅₁ H ₃₁ N ₅ OS=761.9) Sub1-73 m/z=696.22 (C ₄₉ H ₃₂ N ₂ OS=696.87) Sub1-74 m/z=828.26 (C ₅₈ H ₄₀ N ₂ S ₂ =829.09) Sub1-75 m/z=491.13 (C ₃₄ H ₂₁ NOS=491.61) Sub1-76 m/z=551.22 (C ₄₁ H ₂₉ NO=551.69) Sub1-77 m/z=467.17 (C ₃₃ H ₂₅ NS=467.63) Sub1-78 m/z=716.2 (C ₄₈ H ₃₂ N ₂ OS ₂ =716.92) Sub1-79 m/z=889.31 (C ₆₃ H ₄₃ N ₃ OS=890.12) Sub1-80 m/z=675.14 (C ₄₄ H ₂₅ N ₃ OS ₂ =675.82) Sub1-81 m/z=635.15 (C ₄₂ H ₂₅ N ₃ S ₂ =635.8) Sub1-82 m/z=441.16 (C ₃₁ H ₂₃ NS=441.59) Sub1-83 m/z=699.18 (C ₄₇ H ₂₉ N ₃ S ₂ =699.89) Sub1-84 m/z=794.27 (C ₅₆ H ₃₄ N ₄ O ₂ =794.91) Sub1-85 m/z=685.31 (C ₄₉ H ₃₉ N ₃ O=685.87) Sub1-86 m/z=365.09 (C ₂₄ H ₁₅ NOS=365.45) Sub1-87 m/z=628.23 (C ₄₄ H ₂₈ N ₄ O=628.74) Sub1-88 m/z=760.24 (C ₅₁ H ₃₂ N ₆ S=760.92) Sub1-89 m/z=385.15 (C ₂₈ H ₁₉ NO=385.47) Sub1-90 m/z=704.18 (C ₄₆ H ₂₀ D ₅ N ₃ OS ₂ =704.88) Sub1-91 m/z=632.19 (C ₄₄ H ₂₈ N ₂ OS=632.78) Sub1-92 m/z=465.12 (C ₃₂ H ₁₉ NOS=465.57) Sub1-93 m/z=617.28 (C ₄₅ H ₃₅ N ₃ =617.8) Sub1-94 m/z=683.2 (C ₄₅ H ₂₅ N ₅ O ₃ =683.73) Sub1-95 m/z=375.16 (C ₂₇ H ₂₁ NO=375.47) Sub1-96 m/z=738.34 (C ₅₄ H ₄₃ FN ₂ =738.95) Sub1-97 m/z=566.18 (C ₄₀ H ₂₆ N ₂ S=566.72) Sub1-98 m/z=547.11 (C ₃₆ H ₂₁ NOS ₂ =547.69) Sub1-99 m/z=390.08 (C ₂₅ H ₁₄ N ₂ OS=390.46) Sub1-100 m/z=787.23 (C ₅₄ H ₃₃ N ₃ O ₂ S=787.94)

II. Synthesis of Sub 2

The compound belonging to Sub 2 may be a compound as follows, but is not limited thereto. Table 2 below shows FD-MS (Field Desorption-Mass Spectrometry) values of compounds belonging to Sub 2 .

compound FD-MS compound FD-MS Sub2-1 m/z=155.96 (C ₆ H ₅ Br=157.01) Sub2-2 m/z=231.99 (C ₁₂ H ₉ Br=233.11) Sub2-3 m/z=231.99 (C ₁₂ H ₉ Br=233.11) Sub2-4 m/z=308.02 (C ₁₈ H ₁₃ Br=309.21) Sub2-5 m/z=205.97 (C ₁₀ H ₇ Br=207.07) Sub2-6 m/z=205.97 (C ₁₀ H ₇ Br=207.07) Sub2-7 m/z=255.99 (C ₁₄ H ₉ Br=257.13) Sub2-8 m/z=282 (C ₁₆ H ₁₁ Br=283.17) Sub2-9 m/z=160.99 (C ₆ D ₅ Br=162.04) Sub2-10 m/z=181.97 (C ₈ H ₇ Br=183.05) Sub2-11 m/z=322 (C ₁₈ H ₁₁ BrO=323.19) Sub2-12 m/z=429.02 (C ₂₄ H ₁₆ BrNS=430.36) Sub2-13 m/z=488.09 (C ₃₀ H ₂₁ BrN ₂ =489.42) Sub2-14 m/z=328.06 (C ₁₈ H ₉ D ₅ BrN=329.25) Sub2-15 m/z=539.09 (C ₃₄ H ₂₂ BrNO=540.46) Sub2-16 m/z=505.05 (C ₃₀ H ₂₀ BrNS=506.46) Sub2-17 m/z=640.15 (C ₄₂ H ₂₉ BrN ₂ =641.61) Sub2-18 m/z=545.08 (C ₃₃ H ₂₄ BrNS=546.53) Sub2-19 m/z=245.97 (C ₁₂ H ₇ BrO=247.09) Sub2-20 m/z=245.97 (C ₁₂ H ₇ BrO=247.09) Sub2-21 m/z=295.98 (C ₁₆ H ₉ BrO=297.15) Sub2-22 m/z=261.95 (C ₁₂ H ₇ BrS=263.15) Sub2-23 m/z=311.96 (C ₁₆ H ₉ BrS=313.21) Sub2-24 m/z=311.96 (C ₁₆ H ₉ BrS=313.21) Sub2-25 m/z=321.02 (C ₁₈ H ₁₂ BrN=322.21) Sub2-26 m/z=288.01 (C ₁₅ H ₁₃ BrO=289.17) Sub2-27 m/z=385.05 (C ₂₃ H ₁₆ BrN=386.29) Sub2-28 m/z=316.05 (C ₁₈ H ₉ ClN ₄ =316.75) Sub2-29 m/z=267.06 (C ₁₅ H ₁₀ ClN ₃ =267.72) Sub2-30 m/z=379.18 (C ₂₃ H ₂₆ ClN ₃ =379.93) Sub2-31 m/z=357.07 (C ₂₁ H ₁₂ ClN ₃ O=357.8) Sub2-32 m/z=433.1 (C ₂₇ H ₁₆ ClN ₃ O=433.9) Sub2-33 m/z=240.05 (C ₁₄ H ₉ ClN ₂ =240.69) Sub2-34 m/z=387.04 (C ₂₁ H ₁₄ BrN ₃ =388.27)

Ⅲ. Synthesis of final product

1. P-1 Synthesis example

Sub1-1 (4.7 g, 14.0 mmol) obtained in the above synthesis was placed in a round-bottom flask, dissolved in Toluene (70 mL), Sub2-1 (2.1 g, 14.0 mmol), Pd ₂ (dba) ₃ (0.38 g) , 0.42 mmol), P( t -Bu) ₃ (0.17 g, 0.84 mmol), and NaO t -Bu (2.7 g, 28.0 mmol) were added and stirred at 120°C. When the reaction is completed, _{extraction is performed with CH 2} Cl ₂ and water, and the organic layer is dried over _{MgSO 4 and concentrated.} Thereafter, the resulting organic material was recrystallized using a silicagel column to obtain 4.2 g of a product. (yield 72%)

2. P-7 Synthesis example

Sub 1-7 (5.5 g, 9.5 mmol) obtained in the above synthesis was placed in a round-bottom flask and dissolved in Toluene (48 mL), Sub 2-20 (2.3 g, 9.5 mmol), Pd ₂ (dba) ₃ ( 0.26 g, 0.29 mmol), P( t -Bu) ₃ (0.12 g, 0.57 mmol), and NaO t -Bu (1.8 g, 19.0 mmol) were added. g was obtained. (yield 70%)

3. P-22 Synthesis example

Sub 1-20 (7.1 g, 11.7 mmol) obtained in the above synthesis was placed in a round-bottom flask and dissolved in Toluene (58 mL), Sub 2-5 (2.3 g, 11.7 mmol), Pd ₂ (dba) ₃ ( 0.32 g, 0.35 mmol), P( t -Bu) ₃ (0.14 g, 0.70 mmol), and NaO t -Bu (2.2 g, 23.3 mmol) were added, and then tested in the same manner as in P-1 above to produce product 5.9 g was obtained. (Yield 68%)

4. P-93 Synthesis example

Sub 1-75 (8.4 g, 17.1 mmol) obtained in the above synthesis was placed in a round-bottom flask and dissolved in Toluene (85 mL), Sub 2-2 (3.8 g, 17.1 mmol), Pd ₂ (dba) ₃ ( 0.47 g, 0.51 mmol), P( t -Bu) ₃ (0.21 g, 1.03 mmol), and NaO t -Bu (3.3 g, 34.2 mmol) were added. g was obtained. (Yield 74%)

5. P-105 Synthesis example

Sub 1-86 (7.7 g, 21.1 mmol) obtained in the above synthesis was placed in a round-bottom flask and dissolved in Toluene (105 mL), Sub 2-32 (8.8 g, 21.1 mmol), Pd ₂ (dba) ₃ ( 0.58 g, 0.63 mmol), P( t -Bu) ₃ (0.26 g, 1.26 mmol), and NaO t -Bu (4.1 g, 42.1 mmol) were added. g was obtained. (Yield 71%)

Meanwhile, the FD-MS values of the compounds P-1 to P-120 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

compound FD-MS compound FD-MS P-1 m/z=411.16 (C ₃₀ H ₂₁ NO=411.5) P-2 m/z=427.14 (C ₃₀ H ₂₁ NS=427.57) P-3 m/z=486.21 (C ₃₆ H ₂₆ N ₂ =486.62) P-4 m/z=513.25 (C ₃₉ H ₃₁ N=513.68) P-5 m/z=730.3 (C ₅₄ H ₃₈ N ₂ O=730.91) P-6 m/z=786.31 (C ₅₇ H ₄₂ N ₂ S=787.04) P-7 m/z=743.29 (C ₅₄ H ₃₇ N ₃ O=743.91) P-8 m/z=728.28 (C ₅₁ H ₃₇ FN ₂ O ₂ =728.87) P-9 m/z=665.25 (C ₄₈ H ₃₁ N ₃ O=665.8) P-10 m/z=763.3 (C ₅₄ H ₄₁ N ₃ S=764) P-11 m/z=806.28 (C ₅₆ H ₃₄ N ₆ O=806.93) P-12 m/z=746.36 (C ₅₂ H ₂₇ D ₁₀ FN ₄ =746.96) P-13 m/z=731.27 (C ₅₁ H ₃₃ N ₅ O=731.86) P-14 m/z=670.24 (C ₄₈ H ₃₄ N ₂ S=670.87) P-15 m/z=789.28 (C ₅₅ H ₃₉ N ₃ OS=790) P-16 m/z=668.23 (C ₄₈ H ₃₂ N ₂ S=668.86) P-17 m/z=818.29 (C ₆₀ H ₃₈ N ₂ O ₂ =818.98) P-18 m/z=852.26 (C ₆₀ H ₄₀ N ₂ S ₂ =853.11) P-19 m/z=910.34 (C ₆₇ H ₄₆ N ₂ S=911.18) P-20 m/z=593.24 (C ₄₃ H ₃₁ NO ₂ =593.73) P-21 m/z=804.23 (C ₅₅ H ₃₆ N ₂ OS ₂ =805.03) P-22 m/z=734.24 (C ₅₂ H ₃₄ N ₂ OS=734.92) P-23 m/z=734.24 (C ₅₂ H ₃₄ N ₂ OS=734.92) P-24 m/z=829.3 (C ₅₈ H ₃₅ N ₇ =829.97) P-25 m/z=758.24 (C ₅₄ H ₃₄ N ₂ OS=758.94) P-26 m/z=685.19 (C ₄₈ H ₃₁ NS ₂ =685.9) P-27 m/z=768.35 (C ₅₈ H ₄₄ N ₂ =769) P-28 m/z=734.23 (C ₄₈ H ₃₂ F ₂ N ₄ S=734.87) P-29 m/z=743.29 (C ₅₄ H ₃₇ N ₃ O=743.91) P-30 m/z=883.33 (C ₆₆ H ₄₅ NS=884.15) P-31 m/z=617.25 (C ₄₆ H ₃₂ FN=617.77) P-32 m/z=593.18 (C ₄₂ H ₂₇ NOS=593.74) P-33 m/z=795.24 (C ₅₄ H ₂₉ D ₅ N ₂ OS ₂ =796.03) P-34 m/z=804.29 (C ₅₈ H ₃₆ N ₄ O=804.95) P-35 m/z=623.3 (C ₄₅ H ₂₉ D ₅ N ₂ O=623.81) P-36 m/z=754.31 (C ₅₅ H ₃₈ N ₄ =754.94) P-37 m/z=790.21 (C ₅₄ H ₃₄ N ₂ OS ₂ =791) P-38 m/z=964.4 (C ₇₁ H ₅₂ N ₂ O ₂ =965.21) P-39 m/z=828.2 (C ₅₅ H ₃₂ N ₄ OS ₂ =829.01) P-40 m/z=807.29 (C ₅₈ H ₃₇ N ₃ O ₂ =807.95) P-41 m/z=481.11 (C ₃₂ H ₁₉ NO ₂ S=481.57) P-42 m/z=589.22 (C ₄₂ H ₂₇ N ₃ O=589.7) P-43 m/z=664.26 (C ₄₈ H ₃₂ N ₄ =664.81) P-44 m/z=680.19 (C ₄₈ H ₂₈ N ₂ OS=680.83) P-45 m/z=606.18 (C ₄₂ H ₂₆ N ₂ OS=606.74) P-46 m/z=945.23 (C ₆₄ H ₃₉ N ₃ S ₃ =946.22) P-47 m/z=955.27 (C ₆₆ H ₄₁ N ₃ OS ₂ =956.19) P-48 m/z=874.27 (C ₆₂ H ₃₈ N ₂ O ₂ S=875.06) P-49 m/z=879.24 (C ₆₀ H ₃₇ N ₃ OS ₂ =880.1) P-50 m/z=754.21 (C ₅₁ H ₃₄ N ₂ OS ₂ =754.97) P-51 m/z=800.35 (C ₅₄ H ₄₈ N ₄ OS=801.07) P-52 m/z=817.23 (C ₅₄ H ₃₅ N ₅ S ₂ =818.03) P-53 m/z=804.34 (C ₅₇ H ₄₄ N ₂ O ₃ =804.99) P-54 m/z=785.22 (C ₅₃ H ₃₁ N ₅ OS=785.93) P-55 m/z=755.22 (C ₅₀ H ₂₅ D ₅ N ₄ S ₂ =755.97) P-56 m/z=823.27 (C ₅₈ H ₃₇ N ₃ OS=824.01) P-57 m/z=820.36 (C ₆₀ H ₄₄ N ₄ =821.04) P-58 m/z=747.25 (C ₅₁ H ₃₃ N ₅ S=747.92) P-59 m/z=922.31 (C ₆₄ H ₄₆ N ₂ OS ₂ =923.21) P-60 m/z=653.09 (C ₄₂ H ₂₃ NOS ₃ =653.83) P-61 m/z=805.22 (C ₅₄ H ₃₂ FN ₃ O ₂ S=805.93) P-62 m/z=810.26 (C ₅₅ H ₃₄ N ₆ S=810.98) P-63 m/z=884.26 (C ₅₉ H ₄₀ N ₄ OS ₂ =885.12) P-64 m/z=701.16 (C ₄₆ H ₂₇ N ₃ OS ₂ =701.86) P-65 m/z=700.2 (C ₄₈ H ₂₉ FN ₂ OS=700.83) P-66 m/z=961.44 (C ₇₂ H ₅₅ N ₃ =962.25) P-67 m/z=925.35 (C ₆₇ H ₄₇ N ₃ S=926.19) P-68 m/z=793.26 (C ₅₇ H ₃₅ N ₃ S=793.99) P-69 m/z=750.29 (C ₅₃ H ₃₈ N ₂ O ₃ =750.9) P-70 m/z=724.2 (C ₅₀ H ₃₂ N ₂ S ₂ =724.94) P-71 m/z=896.38 (C ₆₇ H ₄₈ N ₂ O=897.13) P-72 m/z=791.29 (C ₅₈ H ₃₇ N ₃ O=791.95) P-73 m/z=721.32 (C ₅₁ H ₃₉ N ₅ =721.91) P-74 m/z=971.3 (C ₆₇ H ₄₅ N ₃ OS ₂ =972.24) P-75 m/z=761.25 (C ₅₃ H ₃₅ N ₃ OS=761.94) P-76 m/z=982.31 (C ₆₉ H ₄₆ N ₂ OS ₂ =983.26) P-77 m/z=896.39 (C ₆₆ H ₄₈ N ₄ =897.14) P-78 m/z=844.25 (C ₆₁ H ₃₆ N ₂ OS=845.03) P-79 m/z=970.21 (C ₆₆ H ₃₈ N ₂ OS ₃ =971.22) P-80 m/z=684.26 (C ₄₉ H ₃₆ N ₂ S=684.9) P-81 m/z=809.38 (C ₆₀ H ₄₇ N ₃ =810.06) P-82 m/z=733.25 (C ₅₂ H ₃₂ FN ₃ O=733.85) P-83 m/z=774.22 (C ₅₄ H ₃₄ N ₂ S ₂ =775) P-84 m/z=774.27 (C ₅₅ H ₃₈ N ₂ OS=774.98) P-85 m/z=834.31 (C ₆₁ H ₄₂ N ₂ S=835.08) P-86 m/z=816.26 (C ₅₇ H ₄₀ N ₂ S ₂ =817.08) P-87 m/z=665.25 (C ₄₈ H ₃₁ N ₃ O=665.8) P-88 m/z=937.29 (C ₆₅ H ₃₉ N ₅ OS=938.12) P-89 m/z=772.25 (C ₅₅ H ₃₆ N ₂ OS=772.97) P-90 m/z=836.24 (C ₅₆ H ₄₀ N ₂ S ₃ =837.13) P-91 m/z=904.29 (C ₆₄ H ₄₄ N ₂ S ₂ =905.19) P-92 m/z=887.24 (C ₆₂ H ₃₇ N ₃ S ₂ =888.12) P-93 m/z=643.2 (C ₄₆ H ₂₉ NOS=643.8) P-94 m/z=753.3 (C ₅₇ H ₃₉ NO=753.95) P-95 m/z=619.23 (C ₄₅ H ₃₃ NS=619.83) P-96 m/z=916.35 (C ₆₆ H ₄₈ N ₂ OS=917.18) P-97 m/z=924.28 (C ₆₃ H ₄₄ N ₂ O ₂ S ₂ =925.18) P-98 m/z=965.34 (C ₆₉ H ₄₇ N ₃ OS=966.22) P-99 m/z=751.18 (C ₅₀ H ₂₉ N ₃ OS ₂ =751.92) P-100 m/z=711.18 (C ₄₈ H ₂₉ N ₃ S ₂ =711.9) P-101 m/z=748.27 (C ₅₂ H ₃₆ N ₄ S=748.95) P-102 m/z=775.21 (C ₅₃ H ₃₃ N ₃ S ₂ =775.99) P-103 m/z=870.3 (C ₆₂ H ₃₈ N ₄ O ₂ =871.01) P-104 m/z=761.34 (C ₅₅ H ₄₃ N ₃ O=761.97) P-105 m/z=762.21 (C ₅₁ H ₃₀ N ₄ O ₂ S=762.89) P-106 m/z=704.26 (C ₅₀ H ₃₂ N ₄ O=704.83) P-107 m/z=836.27 (C ₅₇ H ₃₆ N ₆ S=837.02) P-108 m/z=690.27 (C ₅₁ H ₃₄ N ₂ O=690.85) P-109 m/z=780.21 (C ₅₂ H ₂₄ D ₅ N ₃ OS ₂ =780.97) P-110 m/z=708.22 (C ₅₀ H ₃₂ N ₂ OS=708.88) P-111 m/z=626.24 (C ₄₆ H ₃₀ N ₂ O=626.76) P-112 m/z=697.15 (C ₄₈ H ₂₇ NOS ₂ =697.87) P-113 m/z=849.32 (C ₆₁ H ₄₃ N ₃ S=850.1) P-114 m/z=759.23 (C ₅₁ H ₂₉ N ₅ O ₃ =759.83) P-115 m/z=834.32 (C ₆₁ H ₄₂ N ₂ O ₂ =835.02) P-116 m/z=814.37 (C ₆₀ H ₄₇ FN ₂ =815.05) P-117 m/z=768.26 (C ₅₆ H ₃₆ N ₂ S=768.98) P-118 m/z=789.18 (C ₅₄ H ₃₁ NO ₂ S ₂ =789.97) P-119 m/z=733.29 (C ₄₈ H ₃₉ N ₅ OS=733.93) P-120 m/z=889.28 (C ₆₂ H ₃₉ N ₃ O ₂ S=890.07)

Manufacturing evaluation of organic electric devices

[ Example One] Green organic light emitting device ( hole transport layer )

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a hole transport layer material. First, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1 as a hole injection layer on the ITO layer (anode) formed on the glass substrate. -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Then, on the film, the compound P-1 of the present invention as a hole transport compound was vacuum-deposited to a thickness of 60 nm to form a hole transport layer. After forming the hole transport layer, CBP [4,4'-N,N'-dicarbazole-biphenyl] as a host and Ir(ppy)3 [tris(2-phenylpyridine)-iridium] as a dopant were added on the top of the hole transport layer. By doping at a weight ratio of :5, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) as a hole blocking layer was vacuum-deposited to a thickness of 10 nm, and an electron transport layer Bis(10-hydroxybenzo[h]quinolinato)beryllium ( _{abbreviated as BeBq 2} ) was formed as a film with a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic electroluminescent device.

[ Example 2] to [ Example 11] Green organic light emitting device

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-1 of the present invention as the hole transport layer material.

[ comparative example One]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following comparative compound A was used instead of the compound P-1 of the present invention as the hole transport layer material.

[Comparative compound A]

By applying a forward bias DC voltage to the organic electroluminescent devices of Examples and Comparative Examples prepared as described above, electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and the result of the measurement was based on ^{5000 cd/m 2} In luminance, the lifetime of T95 was measured using a lifetime measuring device manufactured by McScience. Table 4 below shows the results of device fabrication and evaluation.

compound drive voltage electric current
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) T(95) Comparative Example (1) Comparative compound A 6.5 20.0 5000 25.0 73.8 Example (1) P-1 6.0 16.3 5000 30.6 92.7 Example (2) P-5 5.7 15.3 5000 32.7 99.2 Example (3) P-7 5.4 14.9 5000 33.6 97.2 Example (4) P-22 5.5 15.0 5000 33.4 98.2 Example (5) P-40 5.3 14.8 5000 33.9 100.2 Example (6) P-49 5.3 15.3 5000 32.8 99.4 Example (7) P-56 5.4 14.8 5000 33.7 95.3 Example (8) P-66 5.5 15.7 5000 31.8 84.4 Example (9) P-85 5.6 15.4 5000 32.4 90.6 Example (10) P-93 5.8 16.0 5000 31.2 91.8 Example (11) P-115 5.5 15.3 5000 32.6 94.3

Looking at Table 4, when a green organic light emitting device is manufactured using the material for an organic light emitting device of the present invention as a hole transport layer material, the performance of the organic light emitting device can be improved than that of Comparative Example 1 using Comparative Compound A. have.

This results in a change in the value of the energy level (especially the HOMO level) by comparing the compound of the present invention and the comparative compound A, and changes in the physical properties of the compound. Accordingly, as the physical properties of the compound are changed, the charge balance in the light emitting layer is increased, and light emission is performed well inside the light emitting layer rather than the interface of the light emitting layer. As a result, deterioration at the interface of the light emitting layer is also reduced, and it is judged that the driving voltage, efficiency, and lifespan are improved. Therefore, it is judged that this point acts as a major factor in improving device performance during device deposition.

[ Example 12] Red organic light emitting device (phosphor host)

An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a phosphorescent host material. First, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1 as a hole injection layer on the ITO layer (anode) formed on the glass substrate. -phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) film was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as NPB) as a hole transport compound was vacuum-deposited on this film to a thickness of 60 nm to form a hole transport layer did After forming the hole transport layer, the compound P-9 of the present invention as a host and (piq) 2 Ir (acac) [bis- (1-phenyl isoquinolyl) iridium (III) acetylacetonate] as a dopant 95: A light emitting layer with a thickness of 30 nm was deposited on the hole transport layer by doping with 5 weight. (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (abbreviated as BAlq) as a hole blocking layer was vacuum-deposited to a thickness of 10 nm, followed by an electron transport layer. Tris(8-quinolinol)aluminum (abbreviated as Alq3) was deposited to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited as an electron injection layer to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic electroluminescent device.

[ Example 13] to [ Example 20] Red organic light emitting device (host)

An organic electroluminescent device was manufactured in the same manner as in Example 12, except that the compound of the present invention shown in Table 5 was used instead of the compound P-9 of the present invention as a host material.

[ comparative example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 12, except that the following comparative compound B was used instead of the compound P-9 of the present invention as a host material.

[Comparative compound B]

By applying a forward bias DC voltage to the organic electroluminescent devices of Examples and Comparative Examples prepared as described above, electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch, and the result of the measurement was based on ^{2500 cd/m 2} In luminance, the lifetime of T95 was measured using a lifetime measuring device manufactured by McScience. Table 5 below shows the device fabrication and evaluation results.

compound drive voltage electric current
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) T(95) Comparative Example (2) Comparative compound B 6.7 34.2 2500 7.3 75.6 Example (12) P-9 5.7 11.7 2500 21.4 103.0 Example (13) P-13 5.8 11.4 2500 21.8 100.3 Example (14) P-39 5.2 11.1 2500 22.5 102.2 Example (15) P-54 5.3 11.3 2500 22.2 95.4 Example (16) P-64 5.7 10.6 2500 23.6 96.4 Example (17) P-73 5.5 11.4 2500 21.9 84.4 Example (18) P-87 5.5 10.8 2500 23.1 98.2 Example (19) P-106 5.2 10.7 2500 23.4 99.3 Example (20) P-114 5.7 10.7 2500 23.3 105.3

Referring to Table 5, when a red organic light emitting device is manufactured using the material for an organic light emitting device of the present invention as a host material, the driving voltage, efficiency and Lifespan can be improved.

This results in a change in the value of the energy level (especially the LUMO level) by comparing the compound of the present invention with the comparative compound B, and the physical properties of the compound change. Accordingly, as the physical properties of the compound are changed, the charge balance in the light emitting layer is increased, and light emission is performed well inside the light emitting layer rather than the interface of the light emitting layer. As a result, deterioration at the interface of the light emitting layer is also reduced, and it is judged that the driving voltage, efficiency, and lifespan are improved. Therefore, it is judged that this point acts as a major factor in improving device performance during device deposition.

The above description is merely illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are intended to illustrate, not to limit the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all descriptions within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100, 200, 300: organic electric device 110: first electrode
120: hole injection layer 130: hole transport layer
140: porous layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: light efficiency improvement layer 210: buffer layer
220: light emitting auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack

Claims (16)

A compound represented by the following formula (1)
Formula (1)

{In the formula (1),
1) X, Y and Z are independently of each other O, S, NR', CR'R" or absent;
2) R′ and R″ are each independently hydrogen; deuterium; C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ alkenyl group; C ₂ ~ C ₆₀ alkynyl group; C ₁ ~ C ₆₀ alkoxy group; C ₆ ~ C ₆₀ Aryloxy group; C ₆ ~ C _{60 Aryl group; Fluorenyl group; C 2} ~ C ₆₀ Heterocyclic group containing at least one heteroatom of O, N, S, Si and P and a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ fused ring group of an aromatic ring;
3) Ar is a C ₆ ~ C ₆₀ aryl group; Or O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group;
4) R ¹ , R ² , R ³ and R ⁴ are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ Alkenyl group; C ₂ ~ C ₆₀ Alkynyl group; C ₁ ~ C ₆₀ Alkoxy group; C ₆ ~ C ₆₀ Aryloxy group; And -L'-NR ^a R ^b; is selected from the group consisting of, or adjacent a plurality of R ¹ each other, or a plurality of R ² to each other, or a plurality of R ³ to each other, or a plurality of R ⁴ ring by combining to each other, can form,
5) L' is a single bond; C ₆ ~ C ₆₀ Arylene group; fluorenylene group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ An aliphatic ring group; selected from the group consisting of, wherein R ^a and R ^b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; And C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ A fused ring group of an aromatic ring; is selected from the group consisting of,
6) a is an integer from 0 to 4, b and d are each independently an integer from 0 to 3, c is an integer from 0 to 2,
Here, the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group are each deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ ~ C ₂₀ Alkylthio group; C ₁ ~ C ₂₀ Alkoxy group; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₆ ~ C ₂₀ Aryl group; _{C 6} ~ C ₂₀ Aryl group substituted with deuterium; fluorenyl group; C ₂ ~ C ₂₀ A heterocyclic group; C ₃ ~ C ₂₀ Cycloalkyl group; C ₇ ~ C ₂₀ Arylalkyl group; C ₈ ~ C ₂₀ Aryl alkenyl group; And -L'-NR ^a R ^b ; may be further substituted with one or more substituents selected from the group consisting of, and these substituents may be combined with each other to form a ring, where 'ring' is C ₃ ~ C ₆₀ An aliphatic ring or a C ₆ ~ C ₆₀ aromatic ring or C ₂ ~ C ₆₀ heterocyclic ring or a fused ring consisting of a combination thereof, including a saturated or unsaturated ring.}
The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (2) to (6)
Formula (2) Formula (3)

Chemical formula (4) Chemical formula (5) Chemical formula (6)

{In the above formulas (2) to (6),
1) X, Z, Ar, R ¹ , R ² , R ³ , R ⁴ , R′, R″, a and b are the same as defined in claim 1 above,
2) c is an integer from 0 to 2, d and c' are independently integers from 0 to 3, and d' is an integer from 0 to 4.}
The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (7) to (11)
Formula (7) Formula (8)

Chemical formula (9) Chemical formula (10) Chemical formula (11)

{In the above formulas (7) to (11),
1) X, Y, Ar, R ¹ , R ² , R ³ , R ⁴ , R′, R″, a and d are the same as defined in claim 1 above,
2) b and c' are each independently an integer from 0 to 3, c is an integer from 0 to 2, and b' is an integer from 0 to 4.}
The compound according to claim 1, wherein Ar in the formula (1) is represented by the following formula (A)
Formula (A)

{In the formula (A),
1) A and B are each independently a C ₆ ~ C ₂₀ aryl group; Or C ₄ ~ C ₂₀ A heterocyclic group;
2) V ¹ and V ² are each independently a single bond, O, S, NR' or CR'R", with the proviso that V ¹ and V ² are both single bonds, except when they are single bonds;
3) R' and R" are the same as defined in claim 1,
4) The tilde indicates the bonding position.}
The compound according to claim 1, wherein ^{at least one of R 1} to R ⁴ in Formula (1) is represented by the following Formula (B) or Formula (C).

{In the formula (B) or formula (C),
1) L ¹ and L ² are the same as the definition of L' in claim 1 above,
2) Ar ¹ and Ar ² are the same as defined ^{for R a in claim 1,}
3) X ¹ , X ² , X ³ , X ⁴ and X ⁵ are each independently CRx or N, provided that at least one of ^{X 1} , X ² , X ³ , X ⁴ and X ^{5 is N,}
4) wherein Rx is hydrogen; heavy hydrogen; halogen; cyano group; nitro group; C ₆ ~ C ₆₀ Aryl group; O, N, S, Si and P containing at least one heteroatom C ₂ ~ C ₆₀ A heterocyclic group; fluorenyl group; C ₃ ~ C ₆₀ A fused ring group of an aliphatic ring and a C ₆ ~ C _{60 aromatic ring;} C ₁ ~ C ₆₀ Alkyl group; C ₂ ~ C ₆₀ Alkenyl group; C ₂ ~ C ₆₀ Alkynyl group; C ₁ ~ C ₆₀ An alkoxyl group; And C ₆ ~ C ₆₀ An aryloxy group; is selected from the group consisting of,
5) The tilde indicates the bonding position.}
The compound according to claim 1, wherein the compound represented by Formula (1) is any one of the following compounds.

An organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises a single compound or two or more compounds represented by the formula (1) of claim 1
The organic electric device according to claim 7, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.
The organic electric device according to claim 7, wherein the organic material layer is a hole transport layer.
The organic electric device according to claim 7, wherein the organic material layer is a light emitting layer.
The organic electric device according to claim 7, further comprising a light efficiency improving layer formed on at least one surface opposite to the organic material layer among one surface of the anode and the cathode.
The organic electric device according to claim 7, wherein the organic material layer is a light efficiency improving layer.
The organic electric device according to claim 7, wherein the organic material layer includes at least two stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode.
The organic electric device according to claim 7, wherein the organic material layer further comprises a charge generating layer formed between the two or more stacks.
A display device comprising the organic electric device of claim 7; and a controller for driving the display device;
16. The method of claim 15, wherein the organic electric device is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoreceptor (OPC), an organic transistor (organic TFT), and a device for monochromatic or white lighting. electronic device

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