KR20240121926A - 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 the luminous efficiency, stability and lifespan of a device, and an organic electric device and an electronic device using the same.

Description

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT 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 luminescence phenomenon refers to a phenomenon that converts electrical energy into light energy using organic materials. An organic electric device utilizing the organic luminescence phenomenon usually has a structure including an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

Materials used as organic layers in organic electronic devices can be classified according to their function into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials.

The biggest issues with organic light-emitting diodes are their lifespan and efficiency, and as displays become larger in size, these efficiency and lifespan issues must be resolved.

Efficiency, lifespan, and driving voltage are interrelated. As efficiency increases, the driving voltage decreases relatively. As the driving voltage decreases, the crystallization of organic substances due to Joule heating generated during operation decreases, which results in a tendency for the lifespan to increase.

However, simply improving the organic layer does not maximize efficiency. This is because long life and high efficiency can be achieved simultaneously when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.

In addition, in order to solve the problem of luminescence in the hole transport layer in recent organic electroluminescent devices, a luminescence auxiliary layer must exist between the hole transport layer and the luminescence layer, and it is time to develop different luminescence auxiliary layers for each luminescence layer (R, G, B).

Typically, electrons are transferred from the electron transport layer to the emitting layer, and holes are transferred from the hole transport layer to the emitting layer, and excitons are generated through recombination.

However, since the material used in the hole transport layer must have a low HOMO value, most of them have a low T1 value, which causes excitons generated in the emitting layer to move to the hole transport layer, resulting in charge unbalance within the emitting layer and causing light emission at the hole transport layer interface.

If light is emitted at the interface of the hole transport layer, the color purity and efficiency of the organic electronic device deteriorate and the lifespan becomes shorter. Therefore, there is an urgent need for the development of a light-emitting auxiliary layer having a high T1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

Meanwhile, it is necessary to develop a hole injection layer material that has stable properties, that is, a high glass transition temperature, against Joule heating generated when the device is operated while delaying the penetration and diffusion of metal oxide from the anode electrode (ITO), which is one of the causes of the shortened lifespan of organic electric devices, into the organic layer. The low glass transition temperature of the hole transport layer material has the characteristic of reducing the uniformity of the thin film surface when the device is operated, and this 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 materials that can withstand the deposition for a long time, that is, materials with strong heat resistance.

That is, in order to fully demonstrate the excellent characteristics of organic electric devices, it is necessary that the materials forming the organic layers within the devices, such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and luminescent auxiliary layer materials, be supported by stable and efficient materials. However, stable and efficient organic layer materials for organic electric devices have not yet been sufficiently developed. Therefore, the development of new materials is continuously required, and in particular, the development of materials for luminescent auxiliary layers is urgently required.

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

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

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

<Chemical Formula 1>

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

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 the color purity and lifespan of the device can be greatly improved.

Figures 1 to 3 are exemplary diagrams of organic electroluminescent devices according to the present invention.
Figure 4 shows a chemical formula according to one aspect of the present invention.

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

Also, in describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

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

The term "halo" or "halogen" as used herein, unless otherwise stated, means fluorine (F), bromine (Br), chlorine (Cl), or iodine (I).

The term "alkyl" or "alkyl group" as used in the present invention, unless otherwise stated, means a radical of a saturated aliphatic functional group having a single bond of 1 to 60 carbon atoms, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, and a cycloalkyl-substituted alkyl group.

The terms “alkenyl group,” “alkenyl group,” or “alkynyl group,” as used in the present invention, unless otherwise stated, include, but are not limited to, straight-chain or branched-chain groups each having a double bond or triple bond of 2 to 60 carbon atoms.

The term "cycloalkyl" as used in the present invention, unless otherwise stated, means alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

The term “alkoxyl group,” “alkoxy group,” or “alkyloxy group” as used in the present invention means an alkyl group having an oxygen radical attached thereto, and unless otherwise specified, has 1 to 60 carbon atoms, but is not limited thereto.

The term "aryloxyl group" or "aryloxy group" as used in the present invention means an aryl group having an oxygen radical attached thereto, and unless otherwise stated, has 6 to 60 carbon atoms, but is not limited thereto.

The terms "aryl group" and "arylene group" used in the present invention, unless otherwise stated, each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, the aryl group or arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by the participation of adjacent substituents in a bond or reaction. For example, the aryl group can 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 aryl substituted radical has the number of carbon atoms described herein.

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

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

The term "heteroatom" as used herein, unless otherwise stated, represents N, O, S, P or Si.

Additionally, a "heterocyclic group" may also include a ring containing SO ₂ instead of ring-forming carbon. For example, a "heterocyclic group" includes the following compounds:

The term "fluorenyl group" or "fluorenylene group" as used in the present invention, unless otherwise stated, means a monovalent or divalent functional group wherein R, R' and R" in the following structures are all hydrogen, respectively, and a "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes a case where R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

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

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

Unless otherwise stated, the term "ring" as used in the present invention refers to a fused ring composed of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, and includes a saturated or unsaturated ring.

Other heterocyclic compounds or heteroradicals other than the aforementioned heterocyclic compounds contain one or more heteroatoms, but are not limited thereto.

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

Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

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 of the carbons forming the benzene ring, and when a is an integer of 2 or 3, they are bonded as follows, wherein R ¹ may be the same or different, and when a is an integer of 4 to 6, they are bonded to the carbon of the benzene ring in a similar manner, and meanwhile, the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

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

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

<Chemical Formula 1> <Chemical Formula 1-1>

In the above chemical formula 1 and chemical formula 1-1, each symbol can be defined as follows.

1) R ^a and R ^b are independently selected from the group consisting of a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; and a C ₆ to C ₆₀ aryl group; or may be combined with each other to form a ring,

When the above R ^a and R ^b are alkyl groups, they may preferably be C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

When the above R ^a and R ^b are aryl groups, they are preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₂₅ aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, etc.

2) R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₆₀ aryl group; fluorenyl group; C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₃ to C ₆₀ aliphatic ring group; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; and an aryloxy group of C ₆ to C ₃₀ ; or adjacent groups can be bonded to each other to form a ring,

However, at least one of R ³ and R ⁴ is a substituent represented by the chemical formula 1-1,

When the above R ¹ , R ² , R ³ , R ⁴ and R ⁵ are aryl groups, they are preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₂₅ aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When the above R ¹ , R ² , R ³ , R ⁴ and R ⁵ are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When the above R ¹ , R ² , R ³ , R ⁴ and R ⁵ are a fused ring group, it is preferably a fused ring group of a C ₃ to C ₃₀ aliphatic ring and a C ₆ to C ₃₀ aromatic ring, more preferably a fused ring group of a C ₃ to C ₂₄ aliphatic ring and a C ₆ to C ₂₄ aromatic ring.

When the above R ¹ , R ² , R ³ , R ⁴ and R ⁵ are alkyl groups, they may preferably be C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

When the above R ¹ , R ² , R ³ , R ⁴ and R ⁵ are aliphatic ring groups, they may preferably be C ₃ to C ₂₄ aliphatic ring groups.

When the above R ¹ , R ² , R ³ , R ⁴ and R ⁵ are alkoxyl groups, they may preferably be alkoxyl groups having C ₁ to C ₂₄ .

When the above R ¹ , R ² , R ³ , R ⁴ and R ⁵ are aryloxy groups, they may preferably be C ₆ to C ₂₄ aryloxy groups.

3) a is an integer from 0 to 3, and if a is an integer greater than or equal to 2, R ¹ is the same or different,

4) L ¹ , L ² and L ³ are independently selected from the group consisting of a single bond; a C ₆ ~ C ₆₀ arylene group; a fluorenylene group; a fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; and a heterocyclic group of C ₂ ~ C ₆₀ ;

When the above L ¹ , L ² and L ³ are arylene groups, they are preferably C ₆ to C ₃₀ arylene groups, more preferably C ₆ to C ₂₀ arylene groups, such as phenylene, biphenylene, naphthylene, terphenylene, anthracenylene, etc.

When the above L ¹ , L ² and L ³ are fused ring groups, they are preferably fused ring groups of an aliphatic ring of C ₃ to C ₃₀ and an aromatic ring of C ₆ to C ₃₀ , and more preferably fused ring groups of an aliphatic ring of C ₃ to C ₂₄ and an aromatic ring of C ₆ to C ₂₄ .

When the above L ¹ , L ² and L ³ are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₀ heterocyclic groups, such as pyridine, pyrimidine, quinoline, quinazoline, quinoxaline, dibenzofuran, dibenzothiophene, naphthobenzothiophene, naphthobenzofuran, benzofuran, benzothiophene, etc.

5) Ar, Ar ¹ and Ar ² are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; and a C ₃ to C ₆₀ cycloalkyl group;

When the above Ar, Ar ¹ and Ar ² are aryl groups, they are preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₂₅ aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, phenanthrene, etc.

When the above Ar, Ar ¹ and Ar ² are heterocyclic groups, they may preferably be C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When the above Ar, Ar ¹ and Ar ² are fused ring groups, they may preferably be fused ring groups of an aliphatic ring of C ₃ to C ₃₀ and an aromatic ring of C ₆ to C ₃₀ , and more preferably fused ring groups of an aliphatic ring of C ₃ to C ₂₄ and an aromatic ring of C ₆ to C ₂₄ .

When the above Ar, Ar ¹ and Ar ² are cycloalkyl groups, they may preferably be C ₃ to C ₃₀ cycloalkyl groups, more preferably C ₃ to C ₂₄ cycloalkyl groups.

6) means the position where it is combined,

Here, the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the aliphatic ring group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group and the cycloalkyl group are each independently selected from deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C ₁ to C ₂₀ alkylthio group; a C ₁ to C ₂₀ alkoxyl group; a C ₁ to C ₂₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₆ to C ₂₀ aryl group; a C ₆ to C ₂₀ aryl group substituted with deuterium; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group; A C ₃ to C ₂₀ cycloalkyl group; a C ₇ to C ₂₀ arylalkyl group; and a C ₈ to C ₂₀ arylalkenyl group may be further substituted with one or more substituents selected from the group consisting of a C 3 to C 20 cycloalkyl group; a C 7 to C 20 arylalkyl group; and a C 8 to C ₂₀ arylalkenyl group; and further, these substituents may be combined with each other to form a ring, wherein the 'ring' refers to a fused ring formed of a C ₃ to C ₆₀ aliphatic ring, a C ₆ to C 60 aromatic ring, a C ₂ to C ₆₀ heterocycle, or a combination thereof, and includes a saturated or unsaturated ring.

In addition, the present invention provides a compound represented by the chemical formula 1 below, chemical formula 2-1 or chemical formula 2-2.

<Chemical Formula 2-1> <Chemical Formula 2-2>

{In the above chemical formulas 2-1 and 2-2, R ^a , R ^b , Ar, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ¹ , L ² , L ³ , Ar ¹ , Ar ² and a are the same as defined above.}

In addition, the present invention provides a compound in which the chemical formula 1 is represented by any one of the following chemical formulas 2 to 7.

<Chemical Formula 2> <Chemical Formula 3>

<Chemical Formula 4> <Chemical Formula 5>

<Chemical Formula 6> <Chemical Formula 7>

{In the chemical formulas 2 to 7 above,

1) Ar, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ¹ , L ² , L ³ , Ar ¹ , Ar ² and a are as defined above,

2) R ^c and R ^d are independently a C ₁ to C ₅₀ alkyl group; preferably a C ₁ to C ₃₀ alkyl group, more preferably a C ₁ to C ₂₄ alkyl group;

3) R ²⁰ , R ²¹ , R ²² and R ²³ are the same as the definition of R ¹ above, or adjacent groups can combine with each other to form a ring,

4) r and s are independently integers from 0 to 5, and t and u are independently integers from 0 to 4.

In addition, the present invention provides a compound in which at least one of Ar ¹ and Ar ² is represented by any one of the following chemical formulae Ar-1 to Ar-10.

<Chemical Formula Ar-1> <Chemical Formula Ar-2> <Chemical Formula Ar-3> <Chemical Formula Ar-4>

<Chemical formula Ar-5> <Chemical formula Ar-6> <Chemical formula Ar-7>

<Chemical formula Ar-8> <Chemical formula Ar-9> <Chemical formula Ar-10>

In the above chemical formulas Ar-1 to Ar-10, each symbol can be defined as follows.

1) R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are each the same or different and are independently selected from the group consisting of hydrogen; deuterium; a C ₆ to C ₆₀ aryl group; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; and a C ₆ to C ₃₀ aryloxy group; or adjacent groups may be bonded to each other to form a ring,

When the above R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are aryl groups, they are preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₂₅ aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When the above R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are alkyl groups, they may preferably be C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

When the above R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are alkoxyl groups, they may preferably be C ₁ to C ₂₄ alkoxyl groups.

When the above R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are aryloxy groups, they may preferably be C ₆ to C ₂₄ aryloxy groups.

2) X is O, S, NR or CR'R",

3) R ^x and R ^y are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; and a C ₆ to C ₃₀ aryloxy group; or adjacent groups may be bonded to each other to form a ring,

When the above R ^x and R ^y are aryl groups, they are preferably C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₂₅ aryl groups, such as phenyl, biphenyl, terphenyl, naphthalene, etc.

When the above R ^x and R ^y are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, and examples thereof include pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothioenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, and the like.

When the above R ^x and R ^y are alkyl groups, they may preferably be C ₁ to C ₃₀ alkyl groups, and more preferably C ₁ to C ₂₄ alkyl groups.

When the above R ^x and R ^y are alkoxyl groups, they may preferably be alkoxyl groups having C ₁ to C ₂₄ .

When the above R ^x and R ^y are aryloxy groups, they may preferably be C ₆ to C ₂₄ aryloxy groups.

4) R, R' and R" are the same as the definition of R ¹ above, or R' and R" can be combined with each other to form a ring,

5) f, i and o are integers from 0 to 5, g is an integer from 0 to 7, h, l, m and n are independently integers from 0 to 4, j is an integer from 0 to 9, k is an integer from 0 to 3, p is an integer from 0 to 11, q is an integer from 0 to 15,

6) * indicates the position where it is combined.

In addition, the present invention provides a compound wherein Ar ¹ and Ar ² are represented by any one of the compounds of Group A below.

<Group A>

{In the chemical formulas A-1 to A-19, R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , X, R ^x , R ^y , f, g, h, i, j, k, l, m, n, o, p, q and * are the same as defined above.}

In addition, the present invention provides a compound represented by the chemical formula 1 below, chemical formula 3-1 or chemical formula 3-2.

<Chemical Formula 3-1> <Chemical Formula 3-2>

{In the above chemical formulas 3-1 and 3-2,

1) Ar, R ^a , R ^b , R ¹ , R ² , R ⁵ , R ¹¹ , R ¹² , L ¹ , L ² , L ³ , Ar ² , a, k and l are as defined above,

2) Ak is a cycloalkyl group having C ₃ to C ₆₀ , and preferably a cycloalkyl group having C ₃ to C ₂₄ .

Specifically, the compound of the above chemical formula 1 may be any one of the following compounds P-1 to P-96, but is not limited thereto.

In addition, the present invention provides a compound represented by the chemical formula 1 having an RE value of 0.16 to 0.23.

Additionally, preferably, the RE value of the compound represented by the chemical formula 1 may be 0.17 to 0.22.

Reorganization Energy (hereinafter abbreviated as RE) refers to the energy lost due to changes in molecular structure arrangement when charges (electrons, holes) move. It depends on molecular geometry and has the characteristic that its value decreases as the difference between the neutral potential energy surface (hereinafter abbreviated as PES) and the charged PES decreases. The RE value can be obtained by the following calculation formula.

Each argument can be defined as follows:

NONE: Neutral geometry of a neutral molecule (hereinafter, NO opt.)

NOAE: Anion geometry of neutral molecules

NOCE: Cation geometry of a neutral molecule

AONE: Neutral geometry of anion molecules

AOAE: Anion geometry of anion molecules (hereinafter, AO opt.)

CONE: Neutral geometry of cation molecules

COCE: Cation geometry of cation molecules (hereinafter, CO opt.)

The reorganization energy value and mobility are inversely proportional, and under the condition of having the same r and T values, the RE value of each material directly affects the mobility. The relationship between the RE value and mobility is expressed as follows.

Each argument can be defined as follows:

λ : Reorganization energy, μ : mobility, r: dimer displacement, t: intermolecular charge transfer matrix element.

From the above equation, we can see that the lower the RE value, the faster the mobility.

Reorganization energy values require a simulation tool that can calculate potential energy according to molecular structure, and we used Gaussian09 (hereinafter G09) and Jaguar (hereinafter JG) modules from Schrodinger Materials Science. Both G09 and JG are tools that analyze the properties of molecules through quantum mechanical (QM) calculations, and have the function of optimizing molecular structures or calculating energy for a given molecular structure (Single-point energy).

The process of performing QM calculations on molecular structures requires large computational resources, and we use two cluster servers for these calculations. Each cluster server consists of four node workstations and one master workstation, and each node uses a CPU with 36 or more cores to perform molecular QM calculations using parallel computing through symmetric multiprocessing (SMP).

Using G09, the molecular structures optimized in neutral/charge states and their potential energies (NONE/COCE) required for rearrangement energy are calculated. By changing only the charge of the two optimized structures, the charge state potential energy (NOCE) of the structure optimized in neutral state and the neutral state potential energy (CONE) of the structure optimized in charge state are calculated. After that, the rearrangement energy is calculated according to the following relationship.

Since Schrödinger provides a function to automatically perform this type of calculation process, the potential energy for each state was sequentially calculated and the RE value was calculated through the JG module simply by providing the molecular structure (NO) of the basic state.

In addition, in another aspect, the present invention provides a method for reusing a compound represented by the chemical formula 1, including the steps of depositing an organic light-emitting material including a compound represented by the chemical formula 1 in a process for manufacturing an organic light-emitting device; removing impurities from an unrefined organic light-emitting material recovered from a deposition apparatus; recovering the removed impurities; and purifying the recovered impurities to a purity of 99.9% or higher.

The step of removing impurities from the crude organic light-emitting material recovered from the above deposition device may preferably include performing a preliminary purification process to obtain a purity of 98% or higher by recrystallization in a recrystallization solvent.

The above recrystallization solvent may preferably be a polar solvent having a polarity index (PI) of 5.5 to 7.2.

The above recrystallization solvent can preferably be used by mixing a polar solvent having a polarity value of 5.5 to 7.2 and a non-polar solvent having a polarity value of 2.0 to 4.7.

When the above recrystallization solvent is used by mixing a polar solvent and a non-polar solvent, the non-polar solvent can be used in a ratio of 15% (v/v) or less relative to the polar solvent.

The above recrystallization solvent is preferably a single solvent of methylpyrrolidone (N-Methylpyrrolidone; NMP); or a mixed polar solvent in which any one selected from the group consisting of dimethyl imidazolidinone (1,3-Dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide (N,N-Dimethyl formamide), dimethyl acetamide, and dimethyl sulfoxide is mixed with the methylpyrrolidone; or a single solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone; or a mixed nonpolar solvent; Alternatively, a mixture of polar solvent and non-polar solvent can be used.

The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition device in a polar solvent at 90°C to 120°C and then cooling it to 0°C to 5°C to precipitate a crystal.

The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition apparatus in a polar solvent at 90°C to 120°C, cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C to precipitate a crystal.

The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition device in a nonpolar solvent, concentrating the solvent, and precipitating a crystal while removing the nonpolar solvent.

The above preliminary purification process may include a step of first recrystallizing with a polar solvent and then recrystallizing again with a non-polar solvent.

The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing an adsorption separation process to adsorb and remove the impurities by adsorption onto an adsorbent.

The above adsorbent may be activated carbon, silica gel, alumina or a material known for adsorption purposes.

The step of purifying the recovered impurities to a purity of 99.9% or higher may include performing sublimation purification.

Referring to FIG. 1, an organic electric element (100) according to the present invention comprises a first electrode (110), a second electrode (170), and an organic layer comprising a single compound or two or more compounds represented by Chemical Formula 1 between the first electrode (110) and the second electrode (170). At this time, the first electrode (110) may be an anode or positive electrode, and the second electrode (170) may be a cathode or negative electrode, and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic layer may sequentially include a hole injection layer (120), a hole transport layer (130), an emission layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110). At this time, the remaining layers except for the emission layer (140) may not be formed. A hole blocking layer, an electron blocking layer, an emission auxiliary layer (220), a buffer layer (210), etc. may be further included, and the electron transport layer (150), etc. may play the role of a hole blocking layer. (See FIG. 2)

In addition, the organic electric device according to one embodiment of the present invention may further include a protective layer or a light efficiency improvement layer (180). This light efficiency improvement layer may be formed on a surface of both sides of the first electrode that is not in contact with the organic layer or on a surface of both sides of the second electrode that is not in contact with the organic layer. The compound according to one embodiment of the present invention applied to the organic layer may be used as a host or dopant of 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 light emitting layer (140), or a material of a light efficiency improvement layer. Preferably, for example, the compound according to Chemical Formula 1 of the present invention may be used as a material of the light emitting auxiliary layer.

The above organic 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)

Meanwhile, since even with the same core, the band gap, electrical characteristics, and interface characteristics can vary depending on which substituent is bonded at which position, the selection of the core and the combination of sub-substituents bonded to it are also very important, and in particular, when the energy level and T1 value between each organic layer, and the intrinsic characteristics of the material (mobility, interface characteristics, etc.) are optimally combined, both a long lifespan and high efficiency can be achieved.

An organic light emitting device according to one embodiment of the present invention can be manufactured using a PVD (physical vapor deposition) method. For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and an organic layer including 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) is formed thereon, and then a material that can be used as a cathode is deposited thereon, thereby manufacturing the device.

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 deep coating process, and a roll-to-roll process, and an organic electric device is provided, characterized in that the organic layer includes the compound as an electron transport material.

As another specific example, the present invention provides an organic electric device characterized in that a compound of the same or different types represented by the chemical formula 1 is mixed and used in the organic layer.

In addition, the present invention provides a light-emitting auxiliary layer composition comprising a compound represented by the chemical formula 1, and provides an organic electric device comprising the light-emitting auxiliary layer.

In addition, the present invention provides an electronic device including a display device including the above-described organic electric element; and a control unit for driving the display device.

In another aspect, the present invention provides an electronic device characterized in that the organic electroluminescent element is at least one of an organic light-emitting element, an organic solar cell, an organic photoconductor, an organic transistor, and a monochrome or white lighting element. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation systems, game consoles, various TVs, and various computers.

Hereinafter, examples of synthesis of the compound represented by the chemical formula 1 of the present invention and examples of manufacturing the organic electric device of the present invention will be described in detail by way of examples, but the present invention is not limited to the following examples.

[Synthetic example]

The compound represented by chemical formula 1 according to the present invention can be synthesized by reacting Sub 1 and Sub 2 as in the following reaction scheme 1, but is not limited thereto.

<Reaction Formula 1>

(Hal ¹ = I, Br or Cl)

Ⅰ. Synthesis of Sub 1

Sub 1 of the above reaction scheme 1 can be synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.

<Reaction Formula 2>

(Hal ¹ and Hal ² = I, Br or Cl)

1. Synthesis example of Sub 1-1

In a round-bottomed flask, Sub 1-1a (10.0 g, 30.9 mmol) was dissolved in THF (77 mL) and water (26 mL), and then Sub 1-1b (3.8 g, 30.9 mmol), Pd(PPh ₃ ) ₄ (1.1 g, 0.9 mmol), and K ₂ CO ₃ (8.5 g, 61.8 mmol) were added and the reaction was carried out at 60°C. When the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, and then dried over MgSO ₄ and concentrated. The resulting organic material was then purified by silica gel column and recrystallized to obtain 7.4 g of the product. (Yield 74.7%)

2. Synthesis example of Sub 1-9

Sub 1-1a (10.0 g, 30.9 mmol) was dissolved in THF (77 mL) and water (26 mL) in a round-bottomed flask, and then Sub 1-9b (6.6 g, 30.9 mmol), Pd(PPh ₃ ) ₄ (1.1 g, 0.9 mmol), and K ₂ CO ₃ (8.5 g, 61.8 mmol) were added. Using the synthesis method of Sub 1-1 above, 9.7 g of the product was obtained. (Yield 76.4%)

3. Synthesis example of Sub 1-18

1) Synthesis example of Sub 1-18-2

In a round-bottomed flask, Sub 1-18-2a (20.0 g, 55.3 mmol) was dissolved in THF (138 mL) and water (46 mL), and then Sub 1-18-2b (13.0 g, 55.3 mmol), Pd(PPh ₃ ) ₄ (1.9 g, 1.7 mmol), and K ₂ CO ₃ (15.3 g, 11.1 mmol) were added and the reaction was carried out at 40°C. When the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, and then dried over MgSO ₄ and concentrated. The resulting organic material was then purified by silica gel column and recrystallized to obtain 15.2 g of the product. (Yield 64.7%)

2) Synthesis example of Sub 1-18-1

Sub 1-18-2 (15.2 g, 35.7 mmol) was dissolved in THF (120 mL) in a round-bottomed flask, and n-butyllithium 2.5 M solution (31.5 mL, 78.6 mmol) was slowly added dropwise at -78°C. After 30 min, SiMe ₂ Cl ₂ (16.1 g, 125.1 mmol) was slowly added dropwise and stirred for 12 h. When the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, and then dried over MgSO ₄ and concentrated. The resulting organic material was then purified by silica gel column and recrystallized to obtain 7.6 g of the product. (Yield 65.7%)

3) Synthesis example of Sub 1-18

Sub 1-18-1 (7.6 g, 23.5 mmol) was dissolved in THF (59 mL) and water (20 mL) in a round-bottomed flask, and then Sub 1-18b (2.9 g, 23.5 mmol), Pd(PPh ₃ ) ₄ (0.8 g, 0.7 mmol), and K ₂ CO ₃ (6.5 g, 47.0 mmol) were added. Using the synthesis method of Sub 1-1 above, 5.3 g of the product was obtained. (Yield 70.4%)

4. Synthesis example of Sub 1-29

Sub 1-18-1 (10.0 g, 30.9 mmol) was dissolved in THF (77 mL) and water (26 mL) in a round-bottomed flask, and then Sub 1-29b (10.4 g, 30.9 mmol), Pd(PPh ₃ ) ₄ (1.1 g, 0.9 mmol), and K ₂ CO ₃ (8.5 g, 61.8 mmol) were added. Using the synthesis method of Sub 1-1 above, 11.8 g of the product was obtained. (Yield 71.1%)

5. Synthesis example of Sub 1-50

In a round-bottomed flask, Sub 1-50a (10.0 g, 24.8 mmol) was dissolved in THF (62 mL) and water (21 mL), and then Sub 1-50b (5.8 g, 24.8 mmol), Pd(PPh ₃ ) ₄ (0.9 g, 0.7 mmol), and NaOH (2.0 g, 49.6 mmol) were added and the reaction was carried out at 75°C. When the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, and then dried over MgSO ₄ and concentrated. The resulting organic material was then purified by silica gel column and recrystallized to obtain 7.6 g of the product. (Yield 54.9%)

6. Synthesis example of Sub 1-52

Sub 1-52a (10.0 g, 22.4 mmol) was dissolved in THF (56 mL) and water (19 mL) in a round-bottomed flask, and then Sub 1-52b (5.0 g, 22.4 mmol), Pd(PPh ₃ ) ₄ (0.8 g, 0.7 mmol), and K ₂ CO ₃ (6.2 g, 44.9 mmol) were added. Using the synthesis method of Sub 1-1 above, 9.1 g of the product was obtained. (Yield 74.7%)

Compounds belonging to Sub 1 may include, but are not limited to, the compounds below, and the FD-MS (Field Desorption-Mass Spectrometry) values of the compounds below are as shown in Table 1 below.

compound FD-MS compound FD-MS Sub 1-1 m/z=320.08(C ₂₀ H ₁₇ ClSi=320.89) Sub 1-2 m/z=370.09(C ₂₄ H ₁₉ ClSi=370.95) Sub 1-3 m/z=370.09(C ₂₄ H ₁₉ ClSi=370.95) Sub 1-4 m/z=446.13(C ₃₀ H ₂₃ ClSi=447.05) Sub 1-5 m/z=396.11(C ₂₆ H ₂₁ ClSi=396.99) Sub 1-6 m/z=396.11(C ₂₆ H ₂₁ ClSi=396.99) Sub 1-7 m/z=472.14(C ₃₂ H ₂₅ ClSi=473.09) Sub 1-8 m/z=472.14(C ₃₂ H ₂₅ ClSi=473.09) Sub 1-9 m/z=410.09(C ₂₆ H ₁₉ ClOSi=410.97) Sub 1-10 m/z=426.07(C ₂₆ H ₁₉ ClSSi=427.03) Sub 1-11 m/z=436.14(C ₂₉ H ₂₅ ClSi=437.05) Sub 1-12 m/z=558.16(C ₃₉ H ₂₇ ClSi=559.18) Sub 1-13 m/z=560.17(C ₃₉ H ₂₉ ClSi=561.20) Sub 1-14 m/z=502.10(C ₃₂ H ₂₃ ClSSi=503.13) Sub 1-15 m/z=423.17(C ₂₆ H ₆ D ₁₃ ClOSi=424.05) Sub 1-16 m/z=326.13(C ₂₀ H ₂₃ ClSi=326.94) Sub 1-17 m/z=382.09(C ₂₅ H ₁₉ ClSi=382.96) Sub 1-18 m/z=320.08(C ₂₀ H ₁₇ ClSi=320.89) Sub 1-19 m/z=370.09(C ₂₄ H ₁₉ ClSi=370.95) Sub 1-20 m/z=446.13(C ₃₀ H ₂₃ ClSi=447.05) Sub 1-21 m/z=396.11(C ₂₆ H ₂₁ ClSi=396.99) Sub 1-22 m/z=396.11(C ₂₆ H ₂₁ ClSi=396.99) Sub 1-23 m/z=420.11(C ₂₈ H ₂₁ ClSi=421.01) Sub 1-24 m/z=426.07(C ₂₆ H ₁₉ ClSSi=427.03) Sub 1-25 m/z=410.09(C ₂₆ H ₁₉ ClOSi=410.97) Sub 1-26 m/z=436.14(C ₂₉ H ₂₅ ClSi=437.05) Sub 1-27 m/z=560.17(C ₃₉ H ₂₉ ClSi=561.20) Sub 1-28 m/z=485.14(C ₃₂ H ₂₄ ClNSi=486.09) Sub 1-29 m/z=536.14(C ₃₆ H ₂₅ ClOSi=537.13) Sub 1-30 m/z=382.19(C ₂₄ H ₃₁ ClSi=383.05) Sub 1-31 m/z=378.16(C ₂₄ H ₂₇ ClSi=379.01) Sub 1-32 m/z=444.11(C ₃₀ H ₂₁ ClSi=445.03) Sub 1-33 m/z=494.13(C ₃₄ H ₂₃ ClSi=495.09) Sub 1-34 m/z=520.14(C ₃₆ H ₂₅ ClSi=521.13) Sub 1-35 m/z=534.12(C ₃₆ H ₂₃ ClOSi=535.11) Sub 1-36 m/z=550.10(C ₃₆ H ₂₃ ClSSi=551.17) Sub 1-37 m/z=560.17(C ₃₉ H ₂₉ ClSi=561.20) Sub 1-38 m/z=616.24(C ₄₃ H ₃₇ ClSi=617.30) Sub 1-39 m/z=610.15(C ₄₂ H ₂₇ ClOSi=611.21) Sub 1-40 m/z=610.15(C ₄₂ H ₂₇ ClOSi=611.21) Sub 1-41 m/z=462.16(C ₃₁ H ₂₇ ClSi=463.09) Sub 1-42 m/z=500.17(C ₃₄ H ₂₉ ClSi=501.14) Sub 1-43 m/z=494.13(C ₃₄ H ₂₃ ClSi=495.09) Sub 1-44 m/z=444.11(C ₃₀ H ₂₁ ClSi=445.03) Sub 1-45 m/z=544.14(C ₃₈ H ₂₅ ClSi=545.15) Sub 1-46 m/z=550.10(C ₃₆ H ₂₃ ClSSi=551.17) Sub 1-47 m/z=534.12(C ₃₆ H ₂₃ ClOSi=535.11) Sub 1-48 m/z=560.17(C ₃₉ H ₂₉ ClSi=561.20) Sub 1-49 m/z=636.20(C ₄₅ H ₃₃ ClSi=637.29) Sub 1-50 m/z=557.14(C ₃₆ H ₁₆ D ₇ ClSSi=558.22) Sub 1-51 m/z=442.09(C ₃₀ H ₁₉ ClSi=443.02) Sub 1-52 m/z=542.13(C ₃₈ H ₂₃ ClSi=543.14) Sub 1-53 m/z=532.11(C ₃₆ H ₂₁ ClOSi=533.10) Sub 1-54 m/z=442.09(C ₃₀ H ₁₉ ClSi=443.02) Sub 1-55 m/z=518.13(C ₃₆ H ₂₃ ClSi=519.12)

Ⅱ. Synthesis of Sub 2

Sub 2 of the above reaction scheme 1 can be synthesized by the reaction path of the following reaction scheme 3, but is not limited thereto.

<Reaction Formula 3>

(Hal ³ = I, Br or Cl)

1. Synthesis example of Sub 2-10

In a round-bottomed flask, Sub 2-10a (10.0 g, 32.3 mmol) was dissolved in toluene (108 mL), and then Sub 2-10b (6.0 g, 64.7 mmol), Pd ₂ (dba) ₃ (0.9 g, 1.0 mmol), P(t-Bu) ₃ (0.8 mL, 1.9 mmol), and NaOt-Bu (6.2 g, 64.7 mmol) were added and the reaction was carried out at 60°C. When the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, and then dried over MgSO ₄ and concentrated. The resulting organic material was then passed through a silica gel column and recrystallized to obtain 7.8 g of the product. (Yield 75.0%)

2. Synthesis example of Sub 2-20

Sub 2-20a (10.0 g, 41.8 mmol) was dissolved in toluene (139 mL) in a round-bottomed flask, and then Sub 2-20b (14.2 g, 83.6 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.3 mmol), P(t-Bu) ₃ (1.0 mL, 2.5 mmol), NaOt-Bu (8.0 g, 83.6 mmol) were added. Using the synthesis method of Sub 2-10 above, 10.9 g of the product was obtained. (Yield 79.6%)

3. Synthesis example of Sub 2-34

Sub 2-34a (10.0 g, 28.6 mmol) was dissolved in toluene (95 mL) in a round-bottomed flask, and then Sub 2-34b (5.3 g, 57.3 mmol), Pd ₂ (dba) ₃ (0.8 g, 0.9 mmol), P(t-Bu) ₃ (0.7 mL, 1.7 mmol), NaOt-Bu (5.5 g, 57.3 mmol) were added. Using the synthesis method of Sub 2-10, 8.4 g of the product was obtained. (Yield 81.2%)

4. Synthesis example of Sub 2-41

Sub 2-41a (10.0 g, 39.3 mmol) was dissolved in toluene (131 mL) in a round-bottomed flask, and then Sub 2-41b (13.3 g, 78.7 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), P(t-Bu) ₃ (1.0 mL, 2.4 mmol), NaOt-Bu (7.6 g, 78.7 mmol) were added. Using the synthesis method of Sub 2-10, 11.2 g of the product was obtained. (Yield 83.1%)

5. Synthesis example of Sub 2-47

Sub 2-47a (10.0 g, 30.9 mmol) was dissolved in toluene (103 mL) in a round-bottomed flask, and then Sub 2-47b (10.5 g, 61.9 mmol), Pd ₂ (dba) ₃ (0.9 g, 0.9 mmol), P(t-Bu) ₃ (0.8 mL, 1.9 mmol), and NaOt-Bu (5.9 g, 61.9 mmol) were added. Using the synthesis method of Sub 2-10, 9.2 g of the product was obtained. (Yield 72.3%)

6. Synthesis example of Sub 2-57

Sub 2-57a (10.0 g, 40.5 mmol) was dissolved in toluene (135 mL) in a round-bottomed flask, and then Sub 2-57b (16.1 g, 80.9 mmol), Pd ₂ (dba) ₃ (1.1 g, 1.2 mmol), P(t-Bu) ₃ (1.0 mL, 2.4 mmol), NaOt-Bu (7.8 g, 80.9 mmol) were added. Using the synthesis method of Sub 2-10, 11.6 g of the product was obtained. (Yield 78.4%)

Compounds belonging to Sub 2 may include, but are not limited to, the compounds below, and the FD-MS values of the compounds below are as shown in Table 2.

compound FD-MS compound FD-MS Sub 2-1 m/z=169.09(C ₁₂ H ₁₁ N=169.23) Sub 2-2 m/z=179.15(C ₁₂ HD ₁₀ N=179.29) Sub 2-3 m/z=245.12(C ₁₈ H ₁₅ N=245.32) Sub 2-4 m/z=245.12(C ₁₈ H ₁₅ N=245.32) Sub 2-5 m/z=245.12(C ₁₈ H ₁₅ N=245.32) Sub 2-6 m/z=321.15(C ₂₄ H ₁₉ N=321.42) Sub 2-7 m/z=321.15(C ₂₄ H ₁₉ N=321.42) Sub 2-8 m/z=321.15(C ₂₄ H ₁₉ N=321.42) Sub 2-9 m/z=321.15(C ₂₄ H ₁₉ N=321.42) Sub 2-10 m/z=321.15(C ₂₄ H ₁₉ N=321.42) Sub 2-11 m/z=219.10(C ₁₆ H ₁₃ N=219.29) Sub 2-12 m/z=219.10(C ₁₆ H ₁₃ N=219.29) Sub 2-13 m/z=295.14(C ₂₂ H ₁₇ N=295.38) Sub 2-14 m/z=295.14(C ₂₂ H ₁₇ N=295.38) Sub 2-15 m/z=295.14(C ₂₂ H ₁₇ N=295.38) Sub 2-16 m/z=295.14(C ₂₂ H ₁₇ N=295.38) Sub 2-17 m/z=295.14(C ₂₂ H ₁₇ N=295.38) Sub 2-18 m/z=269.12(C ₂₀ H ₁₅ N=269.35) Sub 2-19 m/z=345.15(C ₂₆ H ₁₉ N=345.44) Sub 2-20 m/z=327.20(C ₂₄ H ₂₅ N=327.47) Sub 2-21 m/z=379.23(C ₂₈ H ₂₉ N=379.55) Sub 2-22 m/z=339.20(C ₂₅ H ₂₅ N=339.48) Sub 2-23 m/z=303.13(C ₂₀ H ₁₇ NO ₂ =303.36) Sub 2-24 m/z=431.26(C ₃₂ H ₃₃ N=431.62) Sub 2-25 m/z=385.28(C ₂₈ H ₃₅ N=385.59) Sub 2-26 m/z=285.15(C ₂₁ H ₁₉ N=285.39) Sub 2-27 m/z=259.10(C ₁₈ H ₁₃ NO=259.31) Sub 2-28 m/z=334.15(C ₂₄ H ₁₈ N ₂ =334.42) Sub 2-29 m/z=275.08(C ₁₈ H ₁₃ NS=275.37) Sub 2-30 m/z=409.18(C ₃₁ H ₂₃ N=409.53) Sub 2-31 m/z=409.18(C ₃₁ H ₂₃ N=409.53) Sub 2-32 m/z=423.16(C ₃₁ H ₂₁ NO=423.51) Sub 2-33 m/z=423.16(C ₃₁ H ₂₁ NO=423.51) Sub 2-34 m/z=361.18(C ₂₇ H ₂₃ N=361.49) Sub 2-35 m/z=361.18(C ₂₇ H ₂₃ N=361.49) Sub 2-36 m/z=351.11(C ₂₄ H ₁₇ NS=351.47) Sub 2-37 m/z=361.18(C ₂₇ H ₂₃ N=361.49) Sub 2-38 m/z=351.11(C ₂₄ H ₁₇ NS=351.47) Sub 2-39 m/z=335.13(C ₂₄ H ₁₇ NO=335.41) Sub 2-40 m/z=483.20(C ₃₇ H ₂₅ N=483.61) Sub 2-41 m/z=342.17(C ₂₄ H ₁₀ D ₇ NO=342.45) Sub 2-42 m/z=335.13(C ₂₄ H ₁₇ NO=335.41) Sub 2-43 m/z=423.20(C ₃₂ H ₂₅ N=423.56) Sub 2-44 m/z=351.11(C ₂₄ H ₁₇ NS=351.47) Sub 2-45 m/z=410.18(C ₃₀ H ₂₂ N ₂ =410.52) Sub 2-46 m/z=423.20(C ₃₂ H ₂₅ N=423.56) Sub 2-47 m/z=411.16(C ₃₀ H ₂₁ NO=411.50) Sub 2-48 m/z=417.25(C ₃₁ H ₃₁ N=417.60) Sub 2-49 m/z=417.21(C ₃₀ H ₂₇ NO=417.55) Sub 2-50 m/z=477.16(C ₃₄ H ₂₃ NS=477.62) Sub 2-51 m/z=410.18(C ₃₀ H ₂₂ N ₂ =410.52) Sub 2-52 m/z=437.21(C ₃₃ H ₂₇ N=437.59) Sub 2-53 m/z=431.16(C ₃₀ H ₁₇ D ₄ NS=431.59) Sub 2-54 m/z=437.21(C ₃₃ H ₂₇ N=437.59) Sub 2-55 m/z=375.11(C ₂₆ H ₁₇ NS=375.49) Sub 2-56 m/z=391.14(C ₂₇ H ₂₁ NS=391.53) Sub 2-57 m/z=365.09(C ₂₄ H ₁₅ NOS=365.45) Sub 2-58 m/z=525.25(C ₄₀ H ₃₁ N=525.69) Sub 2-59 m/z=441.12(C ₃₀ H ₁₉ NOS=441.55) Sub 2-60 m/z=441.12(C ₃₀ H ₁₉ NOS=441.55) Sub 2-61 m/z=385.15(C ₂₈ H ₁₉ NO=385.47) Sub 2-62 m/z=325.09(C ₂₂ H ₁₅ NS=325.43) Sub 2-63 m/z=411.20(C ₃₁ H ₂₅ N=411.55)

Ⅲ. Synthesis example of final compound

1. Synthesis example of P-2

In a round-bottomed flask, Sub 1-1 (5.0 g, 15.6 mmol) was dissolved in toluene (52 mL), and then Sub 2-29 (4.3 g, 15.6 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.5 mmol), P(t-Bu) ₃ (0.4 mL, 0.9 mmol), and NaOt-Bu (3.0 g, 31.2 mmol) were added and the reaction was carried out at 110°C. When the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, and then dried over MgSO ₄ and concentrated. The resulting organic material was then purified by silica gel column and recrystallized to obtain 6.5 g of the product. (Yield 74.5%)

2. Synthesis example of P-13

Sub 1-9 (5.0 g, 12.2 mmol) was dissolved in toluene (41 mL) in a round-bottomed flask, and then Sub 2-3 (3.0 g, 12.2 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.4 mmol), P(t-Bu) ₃ (0.3 mL, 0.7 mmol), NaOt-Bu (2.3 g, 24.3 mmol) were added. Using the synthesis method of P-2 above, 5.6 g of the product was obtained. (Yield 74.3%)

3. Synthetic example of P-36

Sub 1-36 (5.0 g, 9.1 mmol) was dissolved in toluene (30 mL) in a round-bottomed flask, and then Sub 2-20 (3.0 g, 9.1 mmol), Pd ₂ (dba) ₃ (0.2 g, 0.3 mmol), P(t-Bu) ₃ (0.2 mL, 0.5 mmol), NaOt-Bu (1.7 g, 18.1 mmol) were added. Using the synthesis method of P-2 above, 5.2 g of the product was obtained. (Yield 68.1%)

4. Synthetic example of P-45

Sub 1-42 (5.0 g, 10.0 mmol) was dissolved in toluene (33 mL) in a round-bottomed flask, and then Sub 2-44 (3.5 g, 10.0 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.3 mmol), P(t-Bu) ₃ (0.2 mL, 0.6 mmol), NaOt-Bu (1.9 g, 20.0 mmol) were added. Using the synthesis method of P-2 above, 5.6 g of the product was obtained. (Yield 68.8%)

5. Synthetic example of P-52

Sub 1-18 (5.0 g, 15.6 mmol) was dissolved in toluene (52 mL) in a round-bottomed flask, and then Sub 2-54 (6.8 g, 15.6 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.5 mmol), P(t-Bu) ₃ (0.4 mL, 0.9 mmol), NaOt-Bu (3.0 g, 31.2 mmol) were added. Using the synthesis method of P-2 above, 6.9 g of the product was obtained. (Yield 61.3%)

6. Synthetic example of P-59

Sub 1-23 (5.0 g, 11.9 mmol) was dissolved in toluene (40 mL) in a round-bottomed flask, and then Sub 2-59 (5.2 g, 11.9 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.4 mmol), P(t-Bu) ₃ (0.3 mL, 0.7 mmol), NaOt-Bu (2.3 g, 23.8 mmol) were added. Using the synthesis method of P-2 above, 6.3 g of the product was obtained. (Yield 64.2%)

7. Synthesis example of P-64

Sub 1-26 (5.0 g, 11.4 mmol) was dissolved in toluene (38 mL) in a round-bottomed flask, and then Sub 2-52 (5.0 g, 11.4 mmol), Pd ₂ (dba) ₃ (0.3 g, 0.3 mmol), P(t-Bu) ₃ (0.3 mL, 0.7 mmol), NaOt-Bu (2.2 g, 22.9 mmol) were added. Using the synthesis method of P-2 above, 5.7 g of the product was obtained. (Yield 59.4%)

8. Synthetic example of P-69

Sub 1-30 (5.0 g, 13.1 mmol) was dissolved in toluene (44 mL) in a round-bottomed flask, and then Sub 2-31 (5.3 g, 13.1 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.4 mmol), P(t-Bu) ₃ (0.3 mL, 0.8 mmol), NaOt-Bu (2.5 g, 26.1 mmol) were added. Using the synthesis method of P-2 above, 7.0 g of the product was obtained. (Yield 70.9%)

9. Synthetic example of P-85

Sub 1-50 (5.0 g, 9.0 mmol) was dissolved in toluene (30 mL) in a round-bottomed flask, and then Sub 2-25 (3.5 g, 9.0 mmol), Pd ₂ (dba) ₃ (0.2 g, 0.3 mmol), P(t-Bu) ₃ (0.2 mL, 0.5 mmol), NaOt-Bu (1.7 g, 17.9 mmol) were added. Using the synthesis method of P-2 above, 5.6 g of the product was obtained. (Yield 68.9%)

10. Synthetic example of P-89

Sub 1-1 (5.0 g, 15.6 mmol) was dissolved in toluene (52 mL) in a round-bottomed flask, and then Sub 2-61 (6.0 g, 15.6 mmol), Pd ₂ (dba) ₃ (0.4 g, 0.5 mmol), P(t-Bu) ₃ (0.4 mL, 0.9 mmol), NaOt-Bu (3.0 g, 31.2 mmol) were added. Using the synthesis method of P-2 above, 7.7 g of the product was obtained. (Yield 73.8%)

Meanwhile, although the exemplary synthetic examples of the present invention represented by Chemical Formula 1 have been described above, they are all based on the Buchwald-Hartwig cross coupling reaction, the Miyaura boration reaction, the Suzuki cross-coupling reaction, the Intramolecular acid-induced cyclization reaction (J. Mater. Chem. 1999, 9, 2095), the Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and the PPh ₃ -mediated reductive cyclization reaction (J. 86-60 Org. Chem. 2005, 70, 5014), and it will be easily understood by those skilled in the art that the above reaction proceeds even if a substituent other than the substituent specified in the specific synthetic examples is combined.

Meanwhile, the FD-MS values of compounds P-1 to P-96 of the present invention manufactured according to the above-described synthetic examples are as shown in Table 3 below.

compound FD-MS compound FD-MS P-1 m/z=605.25(C ₄₄ H ₃₅ NSi=605.86) P-2 m/z=559.18(C ₃₈ H ₂₉ NSSi=559.80) P-3 m/z=619.23(C ₄₄ H ₃₃ NOSi=619.84) P-4 m/z=629.25(C ₄₆ H ₃₅ NSi=629.88) P-5 m/z=743.30(C ₅₅ H ₄₁ NSi=744.02) P-6 m/z=719.39(C ₅₂ H ₅₃ NSi=720.09) P-7 m/z=619.27(C ₄₅ H ₃₇ NSi=619.88) P-8 m/z=695.30(C ₅₁ H ₄₁ NSi=695.98) P-9 m/z=619.23(C ₄₄ H ₃₃ NOSi=619.84) P-10 m/z=619.23(C ₄₄ H ₃₃ NOSi=619.84) P-11 m/z=655.27(C ₄₈ H ₃₇ NSi=655.92) P-12 m/z=705.29(C ₅₂ H ₃₉ NSi=705.98) P-13 m/z=619.23(C ₄₄ H ₃₃ NOSi=619.84) P-14 m/z=759.39(C ₅₄ H ₅₃ NOSi=760.11) P-15 m/z=751.27(C ₅₃ H ₄₁ NSSi=752.06) P-16 m/z=609.19(C ₄₂ H ₃₁ NSSi=609.86) P-17 m/z=745.32(C ₅₅ H ₄₃ NSi=746.04) P-18 m/z=645.29(C ₄₇ H ₃₉ NSi=645.92) P-19 m/z=691.27(C ₅₁ H ₃₇ NSi=691.95) P-20 m/z=783.30(C ₅₇ H ₄₁ NOSi=784.05) P-21 m/z=685.23(C ₄₈ H ₃₅ NSSi=685.96) P-22 m/z=632.31(C ₄₄ H ₂₀ D ₁₃ NOSi=632.92) P-23 m/z=721.34(C ₅₀ H ₂₃ D ₁₃ N ₂ OSi=722.02) P-24 m/z=767.30(C ₅₄ H ₄₅ NSSi=768.11) P-25 m/z=655.24(C ₄₄ H ₃₇ NOSSi=655.93) P-26 m/z=763.36(C ₅₆ H ₄₉ NSi=764.10) P-27 m/z=653.25(C ₄₈ H ₃₅ NSi=653.90) P-28 m/z=683.21(C ₄₈ H ₃₃ NSSi=683.94) P-29 m/z=703.27(C ₅₂ H ₃₇ NSi=703.96) P-30 m/z=809.26(C ₅₈ H ₃₉ NSSi=810.10) P-31 m/z=868.33(C ₆₄ H ₄₄ N ₂ Si=869.15) P-32 m/z=743.26(C ₅₄ H ₃₇ NOSi=743.98) P-33 m/z=819.30(C ₆₀ H ₄₁ NOSi=820.08) P-34 m/z=819.30(C ₆₀ H ₄₁ NOSi=820.08) P-35 m/z=667.23(C ₄₈ H ₃₃ NOSi=667.88) P-36 m/z=841.32(C ₆₀ H ₄₇ NSSi=842.19) P-37 m/z=809.26(C ₅₈ H ₃₉ NSSi=810.10) P-38 m/z=845.35(C ₆₃ H ₄₇ NSi=846.16) P-39 m/z=799.27(C ₅₇ H ₄₁ NSSi=800.11) P-40 m/z=855.34(C ₆₁ H ₄₉ NSSi=856.21) P-41 m/z=743.26(C ₅₄ H ₃₇ NOSi=743.98) P-42 m/z=743.26(C ₅₄ H ₃₇ NOSi=743.98) P-43 m/z=857.34(C ₆₁ H ₄₃ D ₄ NSSi=858.22) P-44 m/z=791.27(C ₅₅ H ₄₁ NOSSi=792.08) P-45 m/z=815.30(C ₅₈ H ₄₅ NSSi=816.15) P-46 m/z=793.28(C ₅₈ H ₃₉ NOSi=794.04) P-47 m/z=681.19(C ₄₈ H ₃₁ NSSi=681.93) P-48 m/z=889.32(C ₆₇ H ₄₃ NSi=890.17) P-49 m/z=801.29(C ₆₀ H ₃₉ NSi=802.06) P-50 m/z=741.25(C ₅₄ H ₃₅ NOSi=741.96) P-51 m/z=605.25(C ₄₄ H ₃₅ NSi=605.86) P-52 m/z=721.32(C ₅₃ H ₄₃ NSi=722.02) P-53 m/z=707.30(C ₅₂ H ₄₁ NSi=707.99) P-54 m/z=669.25(C ₄₈ H ₃₅ NOSi=669.90) P-55 m/z=669.25(C ₄₈ H ₃₅ NOSi=669.90) P-56 m/z=761.26(C ₅₄ H ₃₉ NSSi=762.06) P-57 m/z=735.24(C ₅₂ H ₃₇ NSSi=736.02) P-58 m/z=735.24(C ₅₂ H ₃₇ NSSi=736.02) P-59 m/z=825.25(C ₅₈ H ₃₉ NOSSi=826.10) P-60 m/z=732.26(C ₅₀ H ₂₈ D ₇ NOSSi=733.02) P-61 m/z=813.29(C ₅₈ H ₄₃ NSSi=814.13) P-62 m/z=695.26(C ₅₀ H ₃₇ NOSi=695.94) P-63 m/z=659.26(C ₄₇ H ₃₇ NOSi=659.90) P-64 m/z=837.38(C ₆₂ H ₅₁ NSi=838.18) P-65 m/z=817.37(C ₅₉ H ₅₁ NOSi=818.15) P-66 m/z=819.33(C ₆₁ H ₄₅ NSi=820.12) P-67 m/z=788.36(C ₅₇ H ₄₈ N ₂ Si=789.11) P-68 m/z=785.31(C ₅₇ H ₄₃ NOSi=786.06) P-69 m/z=755.39(C ₅₅ H ₅₃ NSi=756.12) P-70 m/z=787.33(C ₅₄ H ₄₉ NOSSi=788.14) P-71 m/z=765.34(C ₅₅ H ₄₇ NOSi=766.07) P-72 m/z=752.36(C ₅₄ H ₄₈ N ₂ Si=753.08) P-73 m/z=653.25(C ₄₈ H ₃₅ NSi=653.90) P-74 m/z=933.38(C ₇₀ H ₅₁ NSi=934.27) P-75 m/z=819.30(C ₆₀ H ₄₁ NOSi=820.08) P-76 m/z=842.31(C ₆₂ H ₄₂ N ₂ Si=843.12) P-77 m/z=817.25(C ₅₆ H ₃₉ NO ₂ SSi=818.08) P-78 m/z=693.27(C ₄₈ H ₂₃ D ₁₀ NSSi=694.01) P-79 m/z=859.33(C ₆₃ H ₄₅ NOSi=860.14) P-80 m/z=859.33(C ₆₃ H ₄₅ NOSi=860.14) P-81 m/z=783.30(C ₅₇ H ₄₁ NOSi=784.05) P-82 m/z=875.30(C ₆₃ H ₄₅ NSSi=876.20) P-83 m/z=875.30(C ₆₃ H ₄₅ NSSi=876.20) P-84 m/z=700.32(C ₄₈ H ₁₆ D ₁₇ NSSi=701.05) P-85 m/z=906.44(C ₆₄ H ₅₀ D ₇ NSSi=907.35) P-86 m/z=797.26(C ₅₇ H ₃₉ NSSi=798.09) P-87 m/z=757.23(C ₅₄ H ₃₅ NSSi=758.03) P-88 m/z=833.26(C ₆₀ H ₃₉ NSSi=834.12) P-89 m/z=669.25(C ₄₈ H ₃₅ NOSi=669.90) P-90 m/z=769.32(C ₅₄ H ₄₇ NSSi=770.12) P-91 m/z=779.30(C ₅₈ H ₄₁ NSi=780.06) P-92 m/z=731.21(C ₅₂ H ₃₃ NSSi=731.99) P-93 m/z=707.26(C ₅₁ H ₃₇ NOSi=707.95) P-94 m/z=725.22(C ₅₀ H ₃₅ NOSSi=725.98) P-95 m/z=819.33(C ₆₁ H ₄₅ NSi=820.12) P-96 m/z=939.43(C ₇₀ H ₅₇ NSi=940.32)

Manufacturing and Evaluation of Organic Electronics

[Example 1] Red organic electroluminescent device (luminescent auxiliary layer)

First, 4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 70 nm on an ITO layer (anode) formed on a glass substrate to form a hole injection layer, and then N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) as a hole transport compound was vacuum-deposited to a thickness of 70 nm on the hole injection layer to form a hole transport layer.

Next, the compound P-2 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light-emitting auxiliary layer.

Next, on the light-emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as CBP) as a host material and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter abbreviated as (piq) ₂ Ir(acac)) as a dopant material were doped at a weight ratio of 95:5, thereby forming a light-emitting layer by vacuum deposition to a thickness of 40 nm.

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light-emitting layer to form a hole-blocking layer, and tris-(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq ₃ ) was vacuum-deposited to a thickness of 40 nm on the hole-blocking layer to form an electron-transporting layer.

Thereafter, 8-quinolinolato lithium (hereinafter abbreviated as Liq) was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode, thereby manufacturing an organic light emitting device.

[Example 2] to [Example 23]

An organic light-emitting device was manufactured in the same manner as in Example 1, except that compounds P-9 to P-88 of the present invention, described in Table 4 below, were used instead of compound P-2 of the present invention as a light-emitting auxiliary layer material.

[Comparative Example 1] and [Comparative Example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound A or Comparative Compound B was used instead of Compound P-2 of the present invention as a light-emitting auxiliary layer material.

<Comparative Compound A> <Comparative Compound B>

The organic electroluminescence devices manufactured by the examples and comparative examples were subjected to a forward bias DC voltage, and their electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch. As a result of the measurement, the T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a standard luminance of 2500 cd/m ² . Table 4 below shows the results of the device fabrication and evaluation.

compound Driving voltage
(V) electric current
(mA/cm ² ) Brightness
(cd/ ^m2 ) Efficiency
(cd/A) T(95) Comparative example (1) Comparative compound A 5.3 11.0 2500.0 22.7 84.2 Comparative example (2) Comparative compound B 5.5 11.3 2500.0 22.2 82.5 Example (1) Compound (P-2) 4.8 7.4 2500.0 33.8 112.6 Example (2) Compound (P-9) 4.9 7.5 2500.0 33.2 112.3 Example (3) Compound (P-10) 4.9 7.6 2500.0 32.9 111.7 Example (4) Compound (P-13) 5.0 7.8 2500.0 32.2 111.2 Example (5) Compound (P-14) 4.9 7.7 2500.0 32.6 111.5 Example (6) Compound (P-22) 5.0 7.8 2500.0 32.0 118.4 Example (7) Compound (P-27) 5.0 8.4 2500.0 29.7 107.6 Example (8) Compound (P-28) 4.8 8.2 2500.0 30.4 108.7 Example (9) Compound (P-32) 4.9 8.3 2500.0 30.2 108.3 Example (10) Compound (P-33) 5.0 8.4 2500.0 29.8 107.9 Example (11) Compound (P-39) 4.8 8.1 2500.0 30.7 109.5 Example (12) Compound (P-40) 4.8 8.2 2500.0 30.5 109.2 Example (13) Compound (P-47) 4.8 8.7 2500.0 28.8 106.1 Example (14) Compound (P-51) 4.7 8.1 2500.0 30.9 109.8 Example (15) Compound (P-52) 4.6 7.9 2500.0 31.5 110.6 Example (16) Compound (P-53) 4.7 8.0 2500.0 31.1 110.1 Example (17) Compound (P-57) 4.6 7.9 2500.0 31.7 110.9 Example (18) Compound (P-58) 4.6 8.0 2500.0 31.2 110.3 Example (19) Compound (P-73) 4.7 8.6 2500.0 29.1 107.3 Example (20) Compound (P-78) 4.7 8.4 2500.0 29.6 115.8 Example (21) Compound (P-84) 4.7 8.5 2500.0 29.4 116.7 Example (22) Compound (P-87) 4.6 8.8 2500.0 28.4 105.6 Example (23) Compound (P-88) 4.6 8.9 2500.0 28.2 105.2

As can be seen from the results in Table 4 above, when a red organic light-emitting device is manufactured using the material for an organic light-emitting device of the present invention, not only can the driving voltage of the organic light-emitting device be lowered compared to when Comparative Compound A or Comparative Compound B is used, but also the efficiency and lifespan are significantly improved.

First, Comparative Compound A is similar to the compound of the present invention in that it has an amine group substituted at the 3-position of dibenzosilole and additionally has a secondary substituent. However, the compound of the present invention is different in that the secondary substituent is bonded to the 9-position of dibenzosilole, whereas Comparative Compound A has the secondary substituent positioned at the 7-position.

In addition, comparative compound B is identical to the compound of the present invention in that it has a secondary substituent at position 9 of dibenzosilole, but differs from the compound of the present invention in that the amine group is located at position 4, in which the amine group is located at position 2 or 3.

That is, it can be seen that the device performance of the compound of the present invention, which is characterized by having an amine group bonded to the 2nd or 3rd position of the dibenzosilole moiety and additionally having a secondary substituent at the 9th position, is significantly improved compared to comparative compound A or comparative compound B, and it can be confirmed that the compound of the present invention represented by chemical formula 1 has superior device characteristics than other comparative compounds not described in the present specification.

Table 5 below shows the LUMO and T1 energy level values of comparative compound A and compound P-53 of the present invention.

compound Comparative compound A P-53 LUMO (eV) -1.114 -0.974 T1 (eV) 2.522 2.622

Referring to Table 5 above, it can be confirmed that the compound of the present invention has a higher LUMO energy level formed than the comparative compound A. When it has a higher LUMO energy level, it can effectively block electrons passing from the emitting layer to the emitting auxiliary layer. In addition, the compound of the present invention has a higher T1 energy level formed than the comparative compound A. When an exciton generated in the emitting layer passes to the emitting auxiliary layer, the exciton that is not converted into light energy in the emitting layer is consumed as heat energy, etc. in the emitting auxiliary layer, so that the luminescence efficiency decreases. That is, when the compound of the present invention is used in the luminescence auxiliary layer, it appears that the luminescence efficiency is improved because the electrons and exciton passing from the emitting layer to the luminescence auxiliary layer are effectively blocked because the LUMO and T1 energy levels are high.

Table 6 below shows the HOMO energy levels and calculated Reorganization Energy (RE) values of Comparative Compound B and Compound P-73 of the present invention, and the RE values listed in Table 6 below mean values calculated for RE _holes .

compound Comparative compound B P-73 HOMO (eV) -4.969 -4.815 Reorganization Energy (RE) 0.237 0.212

Referring to Table 6 above, the compound of the present invention exhibits a higher HOMO energy level than the comparative compound B. Accordingly, the compound of the present invention can inject holes into the emitting layer more efficiently than the comparative compound B. As a result, it is judged that the accumulation of holes at the interface between the hole transport layer and the emitting layer is reduced, thereby improving the lifespan of the device compared to the comparative compound, and the overall operation of the device is significantly reduced.

In addition, it can be seen that the compound of the present invention has a lower RE value than the comparative compound B. A low RE value means faster hole mobility, i.e., faster HOD. As holes move quickly from the light-emitting auxiliary layer to the light-emitting layer, and also quickly move within the light-emitting layer, the charge balance of holes and electrons within the light-emitting layer increases, so that the device as a whole is expected to exhibit high efficiency and lifespan.

These results suggest that even if the basic skeleton of the molecule is similar to that of the compound of the present invention and Comparative Compound A or Comparative Compound B, the properties of the compound, such as hole characteristics, light efficiency characteristics, energy level, hole injection and mobility characteristics, charge balance of holes and electrons, volume density, and intermolecular distance, may differ significantly to an extent that is difficult to predict depending on the type of substituent, and as a result, the results of the device may be derived significantly to an extent that is difficult to predict.

In addition, the evaluation results of the above-described device fabrication explained the device characteristics in which the compound of the present invention was applied only to the light-emitting auxiliary layer, but the compound of the present invention can be used by applying it to the hole transport layer or by applying it to both the hole transport layer and the light-emitting auxiliary layer.

The above description is merely an example of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are not intended to limit the present invention but to explain it, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all techniques within a scope equivalent thereto should be interpreted as being included in the scope of the rights of the present invention.

100, 200, 300: Organic electric element 110: First electrode
120: Hole injection layer 130: Hole transport layer
140: Emitting 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: 1st electron transport layer 360: 1st 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: 1st stack ST2: 2nd stack

Claims (14)

A compound represented by the following chemical formula 1
<Chemical Formula 1><Chemical Formula 1-1>

{In the above chemical formula 1 and chemical formula 1-1,
1) R ^a and R ^b are independently selected from the group consisting of a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; and a C ₆ to C ₆₀ aryl group; or may be combined with each other to form a ring,
2) R ¹ , R ² , R ³ , R ⁴ and R ⁵ are each independently hydrogen; deuterium; halogen; cyano group; nitro group; C ₆ to C ₆₀ aryl group; fluorenyl group; C ₂ to C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; a C ₃ to C ₆₀ aliphatic ring group; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; and an aryloxy group of C ₆ to C ₃₀ ; or adjacent groups can be bonded to each other to form a ring,
However, at least one of R ³ and R ⁴ is a substituent represented by the chemical formula 1-1,
3) a is an integer from 0 to 3, and if a is an integer greater than or equal to 2, R ¹ is the same or different,
4) L ¹ , L ² and L ³ are independently selected from the group consisting of a single bond; a C ₆ ~ C ₆₀ arylene group; a fluorenylene group; a fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; and a heterocyclic group of C ₂ ~ C ₆₀ ;
5) Ar, Ar ¹ and Ar ² are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a fluorenyl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a fused ring group of a C ₃ to C ₆₀ aliphatic ring and a C ₆ to C ₆₀ aromatic ring; and a C ₃ to C ₆₀ cycloalkyl group;
6)

means the position where it is combined,
Here, the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the aliphatic ring group, the fused ring group, the alkyl group, the alkenyl group, the alkynyl group, the alkoxy group, the aryloxy group and the cycloalkyl group are each independently selected from deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C ₁ to C ₂₀ alkylthio group; a C ₁ to C ₂₀ alkoxyl group; a C ₁ to C ₂₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₆ to C ₂₀ aryl group; a C ₆ to C ₂₀ aryl group substituted with deuterium; a fluorenyl group; a C ₂ to C ₂₀ heterocyclic group; {It may be further substituted with one or more substituents selected from the group consisting of a C ₃ ~ C ₂₀ cycloalkyl group; a C ₇ ~ C ₂₀ arylalkyl group; and a C ₈ ~ C ₂₀ arylalkenyl group; and further, these substituents may be combined with each other to form a ring, wherein the 'ring' refers to a fused ring formed by a C ₃ ~ C ₆₀ aliphatic ring, a C ₆ ~ C ₆₀ aromatic ring, a C ₂ ~ C ₆₀ heterocycle, or a combination thereof, and includes a saturated or unsaturated ring.}
In claim 1, the chemical formula 1 is a compound characterized by being represented by the following chemical formula 2-1 or chemical formula 2-2.
<Chemical Formula 2-1><Chemical Formula 2-2>

{In the above chemical formulas 2-1 and 2-2, R ^a , R ^b , Ar, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ¹ , L ² , L ³ , Ar ¹ , Ar ² and a are the same as defined in claim 1.}
In claim 1, a compound characterized in that at least one of Ar ¹ and Ar ² is represented by any one of the following chemical formulae Ar-1 to Ar-10:
<Chemical Formula Ar-1><Chemical Formula Ar-2><Chemical Formula Ar-3><Chemical Formula Ar-4>

<Chemical formula Ar-5><Chemical formula Ar-6><Chemical formula Ar-7>

<Chemical formula Ar-8><Chemical formula Ar-9><Chemical formula Ar-10>

{In the chemical formulas Ar-1 to Ar-10 above,
1) R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ and R ¹⁷ are each the same or different and are independently selected from the group consisting of hydrogen; deuterium; a C ₆ to C ₆₀ aryl group; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; and a C ₆ to C ₃₀ aryloxy group; or adjacent groups may be bonded to each other to form a ring,
2) X is O, S, NR or CR'R",
3) R ^x and R ^y are independently selected from the group consisting of a C ₆ to C ₆₀ aryl group; a C ₂ to C ₆₀ heterocyclic group including at least one heteroatom selected from O, N, S, Si and P; a C ₁ to C ₅₀ alkyl group; a C ₂ to C ₂₀ alkenyl group; a C ₂ to C ₂₀ alkynyl group; a C ₁ to C ₃₀ alkoxyl group; and a C ₆ to C ₃₀ aryloxy group; or adjacent groups may be bonded to each other to form a ring,
4) R, R' and R" are the same as the definition of R1 in claim 1, or R' and R" can be combined with each other to form a ring,
5) f, i and o are integers from 0 to 5, g is an integer from 0 to 7, h, l, m and n are independently integers from 0 to 4, j is an integer from 0 to 9, k is an integer from 0 to 3, p is an integer from 0 to 11, q is an integer from 0 to 15,
6) * indicates the position where it is combined.
In claim 1, the compound represented by the chemical formula 1 is a compound characterized in that it is one of the following compounds P-1 to P-96.
























In claim 1, a compound characterized in that the RE value of the compound represented by the chemical formula 1 is 0.16 to 0.23
An organic electric device comprising an anode, a cathode, and an organic layer formed between the anode and the cathode, characterized in that the organic layer comprises a single compound or two or more compounds represented by the chemical formula 1 of claim 1.
In claim 6, an organic electric device characterized in that the organic layer includes 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.
In claim 6, an organic electric device characterized in that the organic layer is a light-emitting auxiliary layer.
In the sixth paragraph, an organic electric device further comprising a light efficiency improvement layer formed on at least one surface of the anode and cathode opposite to the organic layer.
In the sixth paragraph, an organic electric device characterized in that the organic layer includes two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on an anode.
In the 10th paragraph, an organic electric device characterized in that the organic material layer further includes a charge generation layer formed between the two or more stacks.
An electronic device comprising a display device including an organic electric element of clause 6; and a control unit for driving the display device;
In claim 12, the organic electric element is characterized in that it is at least one of an organic light-emitting diode (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a monochrome or white lighting element.
A step of depositing an organic light-emitting material including a compound represented by the chemical formula 1 of claim 1 in a manufacturing process of an organic light-emitting device;
A step of removing impurities from an unrefined organic light-emitting material recovered from a deposition device;
A step of recovering the removed impurities; and
A method for reusing a compound represented by chemical formula 1 according to claim 1, comprising a step of purifying the recovered impurities to a purity of 99.9% or higher.

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