KR20230076930A - A plurality of host materials and organic electroluminescent device comprising the sam - Google Patents

Abstract

The present invention relates to a plurality of types of host materials including a first host compound represented by chemical formula 1 and a second host compound represented by chemical formula 2 or chemical formula 3 in an organic light emitting device. When a host material in which compounds with a specific structure are combined is used in a light emitting layer in a device, it is possible to implement an organic light emitting device with excellent light emitting properties such as low voltage driving characteristics and luminous efficiency.

Description

A plurality of host materials and an organic light emitting device including the same {A PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAM}

The present invention relates to a host material for a light emitting layer in an organic light emitting device, and more particularly, to a plurality of types of host materials obtained by combining different host compounds each having a specific structure, and low voltage driving of the device and excellent luminous efficiency by employing the same in the light emitting layer. It relates to an organic light emitting device with significantly improved light emitting characteristics.

Organic light emitting devices can not only be formed on a transparent substrate, but also can be driven at a low voltage of 10 V or less compared to plasma display panels or inorganic electroluminescent (EL) displays, and consume relatively little power. , It has the advantage of being excellent in color, and can show three colors of green, blue, and red, so it has recently become a subject of much interest as a next-generation display device.

However, in order for the organic light emitting device to exhibit the above characteristics, the materials constituting the organic layer in the device, such as hole injection materials, hole transport materials, light emitting materials, electron transport materials, and electron injection materials, are supported by stable and efficient materials. However, the development of stable and efficient organic layer materials for organic light emitting devices has not yet been sufficiently accomplished.

Accordingly, in order to implement a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, further improvement in terms of efficiency and lifespan characteristics is required. In particular, development of materials constituting each organic layer of the organic light emitting device is It is desperately needed.

In addition, in order to obtain maximum efficiency in the light emitting layer, the energy bandgap of the host and the dopant must be properly combined so that holes and electrons can move to the dopant through a stable electrochemical path to form excitons, and a host material that satisfies this and dopant materials are needed.

The inventors of the present invention intend to propose a host material combining a plurality of host compounds capable of improving light emitting properties such as light emitting efficiency, driving voltage, and lifetime.

Therefore, the present invention is to provide a plurality of host materials that can be employed in a light emitting layer in an organic light emitting device to realize light emitting characteristics such as low voltage driving of the device, improved light emitting efficiency, and excellent long lifespan, and an organic light emitting device including the same in the light emitting layer. .

In order to solve the above problems, the present invention provides a plurality of hosts including a first host compound represented by the following [Formula 1] and a second host compound represented by the following [Formula 2] or [Formula 3]. A material and an organic light emitting device including the same in a light emitting layer are provided.

[Formula 1]

[Formula 2]

[Formula 3]

The characteristic structures of [Formula 1] to [Formula 3], specific compounds constituting the plurality of host materials realized thereby, and definitions of each substituent will be described later.

According to the present invention, when a host material in which a compound having a specific structure is combined is used for the light emitting layer in the device, an organic light emitting device having very excellent light emitting characteristics such as low voltage driving characteristics and light emitting efficiency can be realized, which can be usefully used in various display devices. there is.

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

The present invention relates to a plurality of host materials combining host compounds having a specific structure, further combining a compound represented by the following [Formula 2] or [Formula 3] together with a compound represented by the following [Formula 1] When used in the light emitting layer as a plurality of host materials, hole and electron properties are balanced by HOMO and LUMO energy levels, and specifically, the compound represented by [Formula 1] is an electron transport type host compound, together with It is a hole-transporting type host compound represented by [Formula 2] or [Formula 3], and it is possible to form an appropriate energy gap by combining them, so that when used in the light emitting layer, higher luminous efficiency and luminous properties such as long lifespan It is possible to implement an organic light emitting device having a.

(i) First, the compound represented by [Formula 1] according to the present invention is represented by [Structural Formula 1] at a position selected from A ₁ to A ₃ in the dibenzofuran or dibenzothiophene skeleton structure. Characterized in that the structure is combined.

[Formula 1]

In the above [Formula 1],

Y is O or S;

Any one of A ₁ to A ₃ is represented by the following [Structural Formula 1], and the others are hydrogen.

[Structural Formula 1]

In [Structural Formula 1],

L ₁ is a divalent linking group, and is any one selected from structures represented by the following [Structural Formula 2] (* indicates a portion each connected to a divalent linking group).

[Structural Formula 2]

X ₁ is each independently CH or N, and at least one or more of the plurality of Xs is N.

Ar ₁ to Ar ₂ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, It is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

(ii) Next, the compound represented by [Formula 2] according to the present invention structurally introduces a *-L-A structure and an amine structure having a characteristic structure at positions 1 and 4 of the benzene ring (para substitution structure), respectively characterized by one.

[Formula 2]

In the above [Formula 2],

L ₂ is a divalent linking group, and is any one selected from the following [Structural Formula 3] (* indicates a portion connected to each other by a divalent linking group).

[Structural Formula 3]

A ₄ is characterized by being represented by the following [Structural Formula 4] (* indicates a portion connected to L ₂ ).

[Structural Formula 4]

In [Structural Formula 4],

X ₂ is O or S;

R ₁ to R ₄ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a cyano group, a halogen group, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted C 1 group. 24 alkoxy group substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, substituted or unsubstituted arylsilyl group having 1 to 24 carbon atoms, substituted or unsubstituted It is selected from an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

L ₃ and L ₄ are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted carbazolylene group. , A substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted arylene group having 6 to 50 carbon atoms It is selected from a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which one or more cycloalkyls having 3 to 30 carbon atoms are fused, n and m are integers of 0 to 3, respectively, and when n and m are each 2 or more A plurality of L ₃ and L ₄ are the same as or different from each other.

Ar ₃ to Ar ₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms It is selected from substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms in which one or more ringed cycloalkyls having 3 to 30 carbon atoms are fused.

(iii) In addition, the compound represented by the following [Formula 3] according to the present invention is structurally an amine derivative through a linking group at any one of the 4-7 carbon positions of the benzoxazole or benzothiazole derivative as shown below characterized by being connected.

[Formula 3]

In the above [Formula 3],

L ₅ to L ₇ are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted carbazolylene group. , A substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted arylene group having 6 to 50 carbon atoms It is selected from a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which one or more cycloalkyls having 3 to 30 carbon atoms are fused, and o, p and q are each an integer of 0 to 3, wherein o, p and q are When each is 2 or more, a plurality of L ₅ to L ₇ are the same as or different from each other.

Ar ₅ to Ar ₆ are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms It is selected from substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms in which one or more ringed cycloalkyls having 3 to 30 carbon atoms are fused.

X ₃ is O or S;

R is selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

Meanwhile, in the above [Formula 1] to [Formula 3], in the definition of L ₁ to L ₇ , Ar ₁ to Ar ₆ , R and R ₁ to R ₄ , 'substituted or unsubstituted' refers to the L ₁ to L ₇ , Ar ₁ to Ar ₆ , R and R ₁ to R ₄ are each selected from deuterium, a halogen group, a cyano group, a nitro group, a hydroxy group, a silyl group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, an alkenyl group, an alky substituted with one or two or more substituents selected from the group consisting of a yl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, and an amine group, or two or more of the above substituents It means that a substituent is substituted with a linked substituent, or that it does not have any substituent.

For example, a substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, and the like are substituted with other substituents. do.

In addition, the substituted heteroaryl group refers to a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group, and condensed heterocyclic groups thereof, such as a benzquinoline group. , It means that a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with other substituents.

In the present invention, examples of the substituents will be described in detail below, but are not limited thereto.

In the present invention, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but is not limited thereto.

In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, and a cyclohexyl group. Pyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo Octyl group, spirodecyl, spirundecyl, adamantyl, and the like, but are not limited thereto.

In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, one or more heteroatoms being O, S, N, P, B, Si, and Se , Preferably selected from O, N or S, specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.

In the present invention, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 20. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1 -butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited thereto.

In the present invention, the alkynyl group also includes a straight chain or branched chain, may be further substituted by other substituents, and may include ethynyl, 2-propynyl, etc., but is limited thereto It doesn't work.

In the present invention, the alkoxy group may be straight chain or branched chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20, which is a range that does not cause steric hindrance. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , benzyloxy group, p-methylbenzyloxy group, etc., but is not limited thereto.

In the present invention, a deuterated alkyl or alkoxy group, a halogenated alkyl or alkoxy group means an alkyl or alkoxy group in which the alkyl or alkoxy group is substituted with deuterium or a halogen group.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and the like, and examples of a polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, and tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited only to these examples.

,

,

등이 있다.In the present invention, the fluorenyl group is a structure in which two ring organic compounds are linked through one atom, for example

,

,

etc.

,

등이 있다.In the present invention, the fluorenyl group includes the structure of an open fluorenyl group, where the open fluorenyl group is a structure in which one ring compound is disconnected from a structure in which two ring organic compounds are connected through one atom. , for example

,

etc.

,

,

,

등이 있다.In addition, the carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O, for example

,

,

,

etc.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms. In the present invention, for example, a thiophene group , furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyra Zinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa sol group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadia A zolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazine group, a phenothiazine group, and the like, but are not limited thereto.

In the present invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc., and specific examples of such a silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxy phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but are not limited thereto.

In the present invention, the amine group may be -NH ₂ , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., the arylamine group refers to an amine substituted with an aryl, and the alkylamine group refers to an amine substituted with an alkyl. The arylheteroarylamine group refers to an amine substituted with aryl and heteroaryl groups, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted diarylamine group. There is an unsubstituted triarylamine group, and the aryl group and heteroaryl group in the arylamine group and the arylheteroarylamine group may be a monocyclic aryl group or a monocyclic heteroaryl group, or may be a polycyclic aryl group or a polycyclic heteroaryl group. And, the aryl group and heteroaryl group including two or more arylamine groups and arylheteroarylamine groups are monocyclic aryl groups (heteroaryl groups), polycyclic aryl groups (heteroaryl groups), or monocyclic aryl groups (heteroaryl groups). aryl group) and polycyclic aryl group (heteroaryl group) may be included at the same time. In addition, the aryl group and heteroaryl group of the arylamine group and the arylheteroarylamine group may be selected from examples of the aryl group and heteroaryl group described above.

Specific examples of the substituent halogen group used in the present invention include fluorine (F), chlorine (Cl), and bromine (Br).

When the hole transport type host compound represented by [Formula 2] or [Formula 3] is combined with the electron transport type host compound represented by [Formula 1], holes and electrons are formed by the HOMO and LUMO energy levels Since the properties are balanced, an appropriate energy gap can be formed, so that it can be usefully used as a host compound for an organic light emitting device.

Preferred specific examples of the compound represented by [Formula 1] according to the present invention include the following compounds, but are not limited thereto.

Preferred specific examples of the compound represented by [Formula 2] according to the present invention include the following compounds, but are not limited thereto.

Preferred specific examples of the compound represented by [Formula 3] according to the present invention include the following compounds, but are not limited thereto.

As such, the plurality of host materials according to the present invention are each of [Formula 1] to [Formula 3] using a characteristic skeleton exhibiting unique properties and a moiety having unique properties introduced thereto. After synthesizing the compound, it is a new host material that is combined so that hole and electron characteristics are balanced by HOMO and LUMO energy levels, and as a result, when a plurality of host materials according to the present invention are applied to the light emitting layer, low voltage Luminous properties such as driving, excellent luminous efficiency, and long lifespan can be further improved.

In addition, a plurality of host materials according to the present invention may be mixed or stacked in a specific ratio in the light emitting layer, and may be applied to the device according to a general organic light emitting device manufacturing method.

An organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween, and the organic light emitting compound according to the present invention is used in the light emitting layer of the device. Except for this, it can be manufactured using conventional device manufacturing methods and materials.

The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are stacked. For example, it may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer, and may further include a capping layer structure in the organic light emitting device, It is not limited thereto and may include a smaller number or a larger number of organic layers.

An organic layer structure of a preferred organic light emitting device according to the present invention will be described in more detail in Examples to be described later.

In addition, the organic light emitting device according to the present invention uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It can be manufactured by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed by using various polymer materials and using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. Can be made in layers.

As the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO). Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , but conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function so as to easily inject electrons into the organic layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof, and multilayers such as LiF/Al or LiO ₂ /Al. structural materials, etc., but are not limited thereto.

The hole injection material is a material capable of receiving holes well from the anode at a low voltage, and preferably has a highest occupied molecular orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high hole mobility is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

The light emitting material is a material that can emit light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively. A material with good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8- Hydroxy-quinoline aluminum complex (Alq ₃ ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazoles, benzthiazoles, and benzimidazole-based compounds. compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but are not limited thereto. In addition, the light emitting material of the light emitting layer may be implemented as a host-dopant system, and a plurality of host materials according to the present invention may be used as the host material of the light emitting layer.

As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is suitable. Specific examples include an Al complex of 8-hydroxyquinoline, a complex including Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

In addition, the organic light emitting compound according to the present invention may act in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like, on a principle similar to that applied to organic light emitting devices.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to explain the present invention in more detail, and the scope of the present invention is not limited thereto, and various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those who have knowledge.

synthesis example 1: Synthesis of compound 1-1

(One) manufacturing example 1: synthesis of intermediate 1-1-1

1-Bromo-2-chloronaphthalene (10.0 g, 0.041 mol), 2,6-Diphenylpyridin-4-ylboronic acid (13.7 g, 0.050 mol), K ₂ CO ₃ (17.2 g, 0.124 mol), Pd (PPh ₃ ) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to ₄ (1.0 g, 0.001 mol), followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 11.4 g of <Intermediate 1-1-1> (yield: 70.3%).

(2) manufacturing example 2: Synthesis of Compound 1-1

Dibenzo[b,d]furan-1-ylboronic acid (10.0 g, 0.047 mol), intermediate 1-1-1 (22.2 g, 0.057 mol), K ₂ CO ₃ (19.6 g, 0.142 mol), catalyst Pd (OAc ) ₂ (2.7 g, 0.002 mol), ligand X-Phos (2.2 g, 0.005 mol), 200 mL of THF, 50 mL of H ₂ O, and 50 mL of ethanol were added, followed by stirring at 90 °C for 6 hours under reflux. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 15.9 g of <Compound 1-1> (yield: 64.4%).

LC/MS: m/z=523 [(M+1) ⁺ ]

synthesis example 2: Synthesis of compound 1-38

(One) manufacturing example 1: synthesis of intermediate 1-38-1

DMF was added to 2-Bromonaphthalene-1-carboxaldehyde (10.0 g, 0.043 mol), 1-Naphthalenecarboximidamide hydrochloride (17.6 g, 0.085 mol), and K ₂ CO ₃ (11.8 g, 0.085 mol), followed by stirring at 120 °C for 18 hours. reacted After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 13.4 g of <Intermediate 1-38-1> (yield: 58.5%).

(2) manufacturing example 2: Synthesis of compound 1-38

Dibenzo[b,d]furan-1-ylboronic acid (10.0 g, 0.047 mol), intermediate 1-38-1 (30.5 g, 0.057 mol), K ₂ CO ₃ (19.6 g, 0.142 mol), Pd (PPh ₃ ) ₄ (1.1 g, 0.001 mol) was added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 21.2 g of <Compound 1-38> (yield: 71.8%).

LC/MS: m/z=625 [(M+1) ⁺ ]

synthesis example 3: Synthesis of compound 1-58

(One) manufacturing example 1: synthesis of intermediate 1-58-1

2,6-Dibromo-4-chloropyridine (10.0 g, 0.037 mol), 2-Naphthaleneboronic acid (15.2 g, 0.088 mol), K ₂ CO ₃ (30.6 g, 0.221 mol), Pd(PPh ₃ ) ₄ (0.9 g , 0.001 mol) into 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 10.2 g of <Intermediate 1-58-1> (yield: 75.7%).

(2) manufacturing example 2: synthesis of intermediate 1-58-2

Intermediate 1-58-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.3 g, 0.033 mol), KOAc (5.4 g, 0.055 mol), Pd(dppf)Cl ₂ (0.6 g, 0.001 mol) 200 mL of dioxane was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.4 g of <Intermediate 1-58-2> (yield: 67.2%).

(3) manufacturing example 3: synthesis of intermediate 1-58-3

2-Bromo-1-chloronaphthalene (10.0 g, 0.041 mol), intermediate 1-58-2 (22.7 g, 0.050 mol), K ₂ CO ₃ (17.2 g, 0.124 mol), Pd(PPh ₃ ) ₄ (1.0 g , 0.001 mol) into 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 14.4 g of <Intermediate 1-58-3> (yield: 70.7%).

(4) manufacturing example 4: Synthesis of compound 1-58

Dibenzo[b,d]furan-2-ylboronic acid (10.0 g, 0.047 mol), intermediate 1-58-3 (27.9 g, 0.057 mol), K ₂ CO ₃ (19.6 g, 0.142 mol), catalyst Pd (OAc ) ₂ (2.7 g, 0.002 mol), ligand X-Phos (2.2 g, 0.005 mol), 200 mL of THF, 50 mL of H ₂ O, and 50 mL of ethanol were added, followed by stirring at 90 °C for 6 hours under reflux. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 17.8 g of <Compound 1-58> (yield: 60.5%).

LC/MS: m/z=623 [(M+1) ⁺ ]

synthesis example 4: Synthesis of compound 1-75

(One) manufacturing example 1: synthesis of intermediate 1-75-1

DMF was added to 1-Bromo-2-naphthaldehyde (10.0 g, 0.043 mol), 4-Cyanobenzimidamide hydrochloride (15.5 g, 0.085 mol), and K ₂ CO ₃ (11.8 g, 0.085 mol), followed by stirring at 120 °C for 18 hours. reacted After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 12.2 g of <Intermediate 1-75-1> (yield: 58.7%).

(2) manufacturing example 2: Synthesis of compound 1-75

Dibenzo[b,d]furan-1-ylboronic acid (10.0 g, 0.047 mol), intermediate 1-75-1 (27.6 g, 0.057 mol), K ₂ CO ₃ (19.6 g, 0.142 mol), Pd (PPh ₃ ) ₄ (1.1 g, 0.001 mol) was added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 18.8 g of <Compound 1-75> (yield: 69.2%).

LC/MS: m/z=575 [(M+1) ⁺ ]

synthesis example 5: Synthesis of compound 1-132

(One) manufacturing example 1: synthesis of intermediate 1-132-1

DMF was added to 3-Bromo-2-naphthaldehyde (10.0 g, 0.043 mol), benzamidine hydrochloride (13.3 g, 0.085 mol), and K ₂ CO ₃ (11.8 g, 0.085 mol), followed by stirring at 120 °C for 18 hours. . After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 11.8 g of <Intermediate 1-132-1> (yield: 63.3%).

(2) manufacturing example 2: Synthesis of compound 1-132

Dibenzo[b,d]furan-2-ylboronic acid (10.0 g, 0.047 mol), intermediate 132-1 (24.8 g, 0.057 mol), K ₂ CO ₃ (19.6 g, 0.142 mol), Pd(PPh ₃ ) ₄ (1.1 g, 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 17.2 g of <Compound 1-132> (yield: 69.4%).

LC/MS: m/z=525 [(M+1) ⁺ ]

synthesis example 6: Synthesis of compound 1-171

(One) manufacturing example 1: synthesis of intermediate 1-171-1

2,6-Dibromo-4-chloropyridine (10.0 g, 0.037 mol), [4-(4-cyanophenyl)phenyl]boronic acid (19.7 g, 0.088 mol), K ₂ CO ₃ (30.6 g, 0.221 mol), Pd (PPh ₃ ) ₄ (0.9 g, 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 12.8 g of <Intermediate 1-171-1> (yield: 74.2%).

(2) manufacturing example 2: synthesis of intermediate 1-171-2

Intermediate 171-1 (10.0 g, 0.021 mol), Bis(pinacolato)diboron (6.5 g, 0.026 mol), KOAc (4.2 g, 0.043 mol), Pd(dppf)Cl ₂ (0.5 g, 0.001 mol) in dioxane 200 mL was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.1 g of <Intermediate 1-171-2> (yield: 67.8%).

(3) manufacturing example 3: synthesis of intermediate 1-171-3

1-Bromo-2-chloronaphthalene (10.0 g, 0.041 mol), intermediate 1-171-2 (27.8 g, 0.050 mol), K ₂ CO ₃ (17.2 g, 0.124 mol), Pd(PPh ₃ ) ₄ (1.0 g , 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 17.6 g of <Intermediate 1-171-3> (yield: 71.6%).

(4) manufacturing example 4: Synthesis of compound 1-171

Dibenzo[b,d]furan-1-ylboronic acid (10.0 g, 0.044 mol), intermediate 1-171-3 (31.3 g, 0.053 mol), K ₂ CO ₃ (18.2 g, 0.132 mol), catalyst Pd (OAc )2 (2.5 g, 0.002 mol), ligand X-Phos (2.1 g, 0.004 mol), 200 mL of THF, 50 mL of H ₂ O, and 50 mL of ethanol were added, followed by reflux stirring at 90 °C for 6 hours to react. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 20.4 g of <Compound 1-171> (yield: 62.7%).

LC/MS: m/z=741 [(M+1) ⁺ ]

synthesis example 7: Synthesis of compound 1-189

(One) manufacturing example 1: synthesis of intermediate 1-189-1

4,6-Dibromo-2-chloropyrimidine (10.0 g, 0.037 mol), 1-Naphthaleneboronic acid (15.2 g, 0.08 8 mol), K ₂ CO ₃ (30.5 g, 0.220 mol), Pd(PPh ₃ ) ₄ (0.9 g , 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 9.2 g (yield: 68.3%) of <Intermediate 1-189-1>.

(2) manufacturing example 2: synthesis of intermediate 1-189-2

Intermediate 1-189-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.3 g, 0.033 mol), KOAc (5.4 g, 0.055 mol), Pd(dppf)Cl ₂ (0.6 g, 0.001 mol) 200 mL of dioxane was added thereto and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 7.1 g of <Intermediate 1-189-2> (yield: 56.8%).

(3) manufacturing example 3: synthesis of intermediate 1-189-3

1-Bromo-2-chloronaphthalene (10.0 g, 0.041 mol), intermediate 1-189-2 (22.8 g, 0.050 mol), K ₂ CO ₃ (17.2 g, 0.124 mol), Pd(PPh ₃ ) ₄ (1.0 g , 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 14.2 g of <Intermediate 1-189-3> (yield: 69.6%).

(4) manufacturing example 4: Synthesis of compound 1-189

Dibenzo[b,d]thiophen-2-ylboronic acid (10.0 g, 0.044 mol), intermediate 1-189-3 (25.9 g, 0.053 mol), K ₂ CO ₃ (18. 2 g, 0.132 mol), catalyst Pd ( OAc)2 (2.5 g, 0.002 mol), ligand X-Phos (2.1 g, 0.004 mol), 200 mL of THF, 50 mL of H ₂ O, and 50 mL of ethanol were added, followed by stirring at 90 °C for 6 hours under reflux. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 16.2 g of <Compound 1-189> (yield: 57.7%).

LC/MS: m/z=640 [(M+1) ⁺ ]

synthesis example 8: Synthesis of compound 1-196

(One) manufacturing example 1: synthesis of intermediate 1-196-1

DMF was added to 2-Bromo-1-naphthaldehyde (10.0 g, 0.043 mol), 2-Naphthimidamide hydrochloride (17.6 g, 0.085 mol), and K ₂ CO ₃ (11.8 g, 0.085 mol), followed by stirring at 120 °C for 18 hours. reacted After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 13.3 g of <Intermediate 1-196-1> (yield: 58.1%).

(2) manufacturing example 2: Synthesis of compound 1-196

Dibenzo[b,d]thiophen-1-ylboronic acid (10.0 g, 0.044 mol), intermediate 1-196-1 (28.3 g, 0.053 mol), K ₂ CO ₃ (18.2 g, 0.132 mol), Pd (PPh ₃ ) ₄ (1.0 g, 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 19.4 g of <Compound 1-196> (yield: 68.9%).

LC/MS: m/z=641 [(M+1) ⁺ ]

synthesis example 9: Synthesis of compound 1-210

(One) manufacturing example 1: synthesis of intermediate 1-210-1

2,6-Dibromo-4-chloropyridine (10.0 g, 0.037 mol), 4-Biphenylboronic acid (17.5 g, 0.088 mol), K ₂ CO ₃ (30.6 g, 0.221 mol), Pd(PPh ₃ ) ₄ (0.9 g , 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 10.8 g of <Intermediate 1-210-1> (yield: 70.1%).

(2) manufacturing example 2: synthesis of intermediate 1-210-2

Intermediate 1-210-1 (10.0 g, 0.024 mol), Bis(pinacolato)diboron (7.3 g, 0.029 mol), KOAc (4.7 g, 0.048 mol), Pd(dppf)Cl ₂ (0.5 g, 0.001 mol) 200 mL of dioxane was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.1 g of <Intermediate 1-210-2> (yield: 66.5%).

(3) manufacturing example 3: synthesis of intermediate 1-210-3

2-Bromo-1-chloronaphthalene (10.0 g, 0.041 mol), intermediate 1-210-2 (25.3 g, 0.050 mol), K ₂ CO ₃ (17.2 g, 0.124 mol), Pd(PPh ₃ ) ₄ (1.0 g , 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 16.8 g of <Intermediate 1-210-3> (yield: 74.6%).

(4) manufacturing example 4: Synthesis of compound 1-210

Dibenzo[b,d]thiophen-2-ylboronic acid (10.0 g, 0.044 mol), intermediate 1-210-3 (28.6 g, 0.053 mol), K ₂ CO ₃ (18.2 g, 0.132 mol), catalyst Pd(OAc ) ₂ (2.5 g, 0.002 mol), ligand X-Phos (2.1 g, 0.004 mol), 200 mL of THF, 50 mL of H ₂ O, and 50 mL of ethanol were added and reacted at 90 °C for 6 hours under reflux stirring. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 18.1 g of <Compound 1-210> (yield: 59.7%).

LC/MS: m/z=691 [(M+1) ⁺ ]

synthesis example 10: synthesis of compound 1-254

(One) manufacturing example 1: synthesis of intermediate 1-254-1

2,6-Dibromo-4-chloropyridine (10.0 g, 0.037 mol), 2-Naphthaleneboronic acid (15.2 g, 0.088 mol), K ₂ CO ₃ (30.6 g, 0.221 mol), Pd(PPh ₃ ) ₄ (0.8 g , 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.1 g of <Intermediate 1-254-1> (yield: 60.1%).

(2) manufacturing example 2: synthesis of intermediate 1-254-2

Intermediate 1-254-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.3 g, 0.033 mol), KOAc (5.4 g, 0.055 mol), Pd(dppf)Cl ₂ (0.6 g, 0.001 mol) 200 mL of dioxane was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 8.1 g of <Intermediate 1-254-2> (yield: 64.8%).

(3) manufacturing example 3: synthesis of intermediate 1-254-3

9-Bromo-10-chlorophenanthrene (10.0 g, 0.034 mol), intermediate 1-254-2 (18.8 g, 0.041 mol), K ₂ CO ₃ (14.2 g, 0.103 mol), Pd(PPh ₃ ) ₄ (0.8 g , 0.001 mol), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 13.1 g of <Intermediate 1-254-3> (yield: 70.5%).

(4) manufacturing example 4: Synthesis of compound 1-254

Dibenzo[b,d]thiophen-1-ylboronic acid (10.0 g, 0.044 mol), intermediate 1-254-3 (28.5 g, 0.053 mol), K ₂ CO ₃ (18.2 g, 0.132 mol), catalyst Pd(OAc ) ₂ (2.5 g, 0.002 mol), ligand X-Phos (2.1 g, 0.004 mol), 200 mL of THF, 50 mL of H ₂ O, and 50 mL of ethanol were added and reacted at 90 °C for 6 hours under reflux stirring. After completion of the reaction, the mixture was extracted, concentrated, and recrystallized with a column to obtain 17.8 g of <Compound 1-254> (yield: 58.9%).

LC/MS: m/z=689 [(M+1) ⁺ ]

synthesis example 11: synthesis of compound 2-3

(One) manufacturing example 1: synthesis of intermediate 2-3-1

100 mL of polyphosphoric acid was added to 2-aminophenol (10.0 g, 0.092 mol) and 2-Bromo-1-naphthoic acid (25.31 g, 0.101 mol), followed by reflux stirring at 150 °C for 5 hours to react. After completion of the reaction, it is neutralized with a saturated NaOH aqueous solution. After extraction and concentration, 22.5 g (yield 75.7%) of <Intermediate 2-3-1> was obtained by column.

(2) manufacturing example 2: Synthesis of compound 2-3

Intermediate 2-3-1 (10.0 g, 0.031 mol), 4-(Dibiphenyl-4-ylamino)phenylboronic acid (16.34 g, 0.037 mol), K ₂ CO ₃ (12.79 g, 0.093 mol), Pd (PPh ₃ ) ₄ (0.71 g, 0.6 mmol) was added with 160 mL of Toluene, 40 mL of EtOH, and 40 mL of H ₂ O, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, 15.0 g (yield 75.9%) of <Compound 2-3> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=640 [(M+1) ⁺ ]

synthesis example 12: synthesis of compounds 2-5

(One) manufacturing example 1: synthesis of intermediate 2-5-1

100 mL of 4-Amino-3-hydroxybenzonitrile (10.0 g, 0.075 mol), 2-Bromo-1-naphthoic acid (20.59 g, 0.082 mol), and polyphosphoric acid were added and reacted by stirring under reflux at 150 °C for 5 hours. . After completion of the reaction, it is neutralized with a saturated NaOH aqueous solution. After extraction and concentration, 19.5 g (yield 74.9%) of <Intermediate 2-5-1> was obtained by column.

(2) manufacturing example 2: Synthesis of Compounds 2-5

Intermediate 2-5-1 (10.0 g, 0.029 mol), 4-(Dibiphenyl-4-ylamino)phenylboronic acid (15.17 g, 0.034 mol), K ₂ CO ₃ (11.87 g, 0.086 mol), Pd (PPh ₃ ) 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O were added to ₄ (0.66 g, 0.6 mmol), followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, 14.3 g (yield 75.0%) of <Compound 2-5> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=665 [(M+1) ⁺ ]

synthesis example 13: synthesis of compound 2-17

(One) manufacturing example 1: Synthesis of compound 2-17

Intermediate 2-3-1 (10.0 g, 0.031 mol), 4-(Dinaphthalen-2-ylamino)phenylboronic acid (14.41 g, 0.037 mol), K ₂ CO ₃ (12.79 g, 0.093 mol), Pd(PPh ₃ ) Toluene 160 mL, Ethanol 40 mL, and H ₂ O 40 mL were added to ₄ (0.71 g, 0.6 mmol) and reacted by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, followed by column and recrystallization to obtain 13.0 g of <Compound 2-17> (yield: 71.6%).

LC/MS: m/z=588 [(M+1) ⁺ ]

synthesis example 14: synthesis of compound 2-80

(One) manufacturing example 1: synthesis of intermediate 2-80-1

100 mL of polyphosphoric acid was added to 2-Aminobenzenethiol (10.0 g, 0.080 mol) and 2-Bromo-1-naphthoic acid (22.06 g, 0.088 mol), followed by reflux stirring at 150 °C for 5 hours. After completion of the reaction, it is neutralized with a saturated NaOH aqueous solution. After extraction and concentration, 20.0 g (yield 73.6%) of <Intermediate 2-80-1> was obtained by column.

(2) manufacturing example 2: synthesis of intermediate 2-80-2

4-Biphenylamine (10.0 g, 0.059 mol), 2-Bromo-11,11-dimethyl-11H-benzo[b]fluorine (28.65 g, 0.089 mol), NaOtBu (11.36 g, 0.118 mol), t-Bu ₃ P (1.20 g, 0.006 mol) and Pd(dba) ₂ (1.70 g, 0.003 mol) were added with 280 mL of Toluene, followed by stirring under reflux at 70 °C for 4 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 18.0 g of <Intermediate 2-80-2> (yield: 74.0%).

(3) manufacturing example 3: synthesis of intermediate 2-80-3

Intermediate 2-80-2 (10.0 g, 0.024 mol), 1-Bromo-4-iodobenzene (10.31 g, 0.036 mol), NaO ^t Bu (4.67 g, 0.049 mol), t-Bu ₃ P (0.49 g, 0.002 mol) and Pd(dba) ₂ (0.70 g, 0.001 mol) into 120 mL of toluene, followed by stirring under reflux at 100 °C for 5 hours. After completion of the reaction, the mixture was extracted, concentrated, and columnized to obtain 10.0 g (yield: 72.6%) of <Intermediate 2-80-3>.

(4) manufacturing example 4: synthesis of intermediate 2-80-4

Intermediate 2-80-3 (10.0 g, 0.018 mol), Bis(pinacolato)diboron (5.38 g, 0.021 mol), KOAc (3.46 g, 0.035 mol), Pd(dppf)Cl ₂ (1.29 g, 0.002 mol) 100 mL of dioxane was added and reacted by stirring at 100 °C for 12 hours. After completion of the reaction, 7.3 g (yield 67.4%) of <Intermediate 2-80-4> was obtained by extraction and concentration, followed by column and recrystallization.

(5) manufacturing example 5: Synthesis of compound 2-80

Intermediate 2-80-1 (10.0 g, 0.029 mol), Intermediate 2-80-4 (21.64 g, 0.035 mol), K ₂ CO ₃ (12.19 g, 0.088 mol), Pd(PPh ₃ ) ₄ (0.68 g, 0.6 mmol) into 140 mL of Toluene, 33 mL of EtOH, and 33 mL of H ₂ O, followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, 12.3 g (yield: 56.0%) of <Compound 2-80> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=746 [(M+1) ⁺ ]

synthesis example 15: synthesis of compound 2-90

(One) manufacturing example 1: synthesis of intermediate 2-90-1

100 mL of polyphosphoric acid was added to 2-Aminobenzenethiol (10.0 g, 0.080 mol) and 1-Bromo-2-naphthoic acid (22.06 g, 0.088 mol), followed by stirring at 150 °C for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 19.9 g of <Intermediate 2-90-1> (yield: 73.2%).

(2) manufacturing example 2: Synthesis of compound 2-90

Intermediate 2-90-1 (10.0 g, 0.029 mol), 4-(Biphenyl-4-yl(phenyl)amino)phenylboronic acid (12.88 g, 0.035 mol), K ₂ CO ₃ (12.19 g, 0.088 mol), Pd 140 mL of Toluene, 33 mL of EtOH, and 33 mL of H ₂ O were added to (PPh ₃ ) ₄ (0.68 g, 0.6 mmol), followed by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, after extraction and concentration, 12.0 g (yield 70.3%) of <Compound 2-90> was obtained by column and recrystallization.

LC/MS: m/z=580 [(M+1) ⁺ ]

synthesis example 16: synthesis of compound 3-2

(One) manufacturing example 1: Synthesis of compound 3-2

6-Bromo-2-phenyl-benzooxazole (10.0 g, 0.037 mol), Bis(4-biphenylyl)amine (17.6 g, 0.055 mol), NaO ^t Bu (7.0 g, 0.073 mol), Pd(dba) ₂ (1.1 g, 0.002 mol) and t-Bu ₃ P (0.7 g, 0.004 mol) were added with 120 mL of toluene, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 13.4 g (yield 71.4%) of <Compound 3-2> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=514 [(M+1) ⁺ ]

synthesis example 17: synthesis of compounds 3-16

(One) manufacturing example 1: synthesis of intermediate 3-16-1

2-Bromo-9,9'-spirobi[9H-fluorene] (10.0 g, 0.025 mol), 2-Amino-9,9-dimethylfluorene (7.9 g, 0.038 mol), NaO ^t Bu (4.9 g, 0.051 mol) , Pd(dba) ₂ (0.7 g, 0.001 mol), and t-Bu ₃ P (0.5 g, 0.003 mol) were added with 120 mL of toluene, followed by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 8.4 g of <Intermediate 3-16-1> (yield: 63.4%).

(2) manufacturing example 2: synthesis of intermediate 3-16-2

1-Bromo-2-iodobenzene (10.0 g, 0.035 mol), intermediate 3-16-1 (27.8 g, 0.053 mol), NaO ^t Bu (6.8 g, 0.071 mol), Pd(dba) ₂ (1.0 g, 0.002 mol), t-Bu ₃ P (0.7 g, 0.004 mol) into toluene 120 mL was reacted by stirring at 100 ℃ for 6 hours. After completion of the reaction, 14.2 g (yield: 59.2%) of <Intermediate 3-16-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: Synthesis of compounds 3-16

(2-Phenylbenzo[d]oxazol-6-yl)boronic acid (10.0 g, 0.042 mol), intermediate 3-16-2 (34.1 g, 0.050 mol), K ₂ CO ₃ (17.4 g, 0.126 mol), Pd 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to (PPh ₃ ) ₄ (1.0 g, 0.001 mol), followed by stirring at 100 °C for 6 hours. After completion of the reaction, 19.4 g (yield: 58.5%) of <Compound 3-16> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=792 [(M+1) ⁺ ]

synthesis example 18: synthesis of compounds 3-44

(One) manufacturing example 1: synthesis of intermediate 3-44-1

2'-Bromo-2-iodobiphenyl (10.0 g, 0.028 mol), dinaphthylamine (11.3 g, 0.042 mol), NaO ^t Bu (5.4 g, 0.056 mol), Pd(dba) ₂ (0.8 g, 0.001 mol), t 120 mL of toluene was added to -Bu ₃ P (0.6 g, 0.003 mol), followed by stirring at 100 °C for 6 hours. After completion of the reaction, 9.2 g (yield 66.0%) of <Intermediate 3-44-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) manufacturing example 2: Synthesis of compounds 3-44

(2-Phenyl-1,3-benzoxazol-5-yl)boronic acid (10.0 g, 0.042 mol), intermediate 44-1 (25.1 g, 0.050 mol), K ₂ CO ₃ (17.4 g, 0.126 mol), Pd 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to (PPh ₃ ) ₄ (1.0 g, 0.001 mol), followed by stirring at 100 °C for 6 hours. After completion of the reaction, 16.4 g (yield 63.8%) of <Compound 44> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=614 [(M+1) ⁺ ]

synthesis example 19: synthesis of compound 3-173

(One) manufacturing example 1: synthesis of intermediate 3-173-1

5-Bromo-7,7-dimethyl-7H-benzo[c]fluorene (10.0 g, 0.031 mol), 4-Aminobiphenyl (7.9 g, 0.046 mol), NaOtBu (6.0 g, 0.062 mol), Pd(dba) ₂ (0.9 g, 0.002 mol) and t-Bu ₃ P (0.6 g, 0.003 mol) into 120 mL of toluene, followed by stirring at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 9.2 g of <Intermediate 3-173-1> (yield: 72.3%).

(2) manufacturing example 2: synthesis of intermediate 3-173-2

1-Bromo-3-iodobenzene (10.0 g, 0.035 mol), intermediate 3-173-1 (21.8 g, 0.053 mol), NaO ^t Bu (6.8 g, 0.071 mol), Pd(dba) ₂ (1.0 g, 0.002 mol), t-Bu ₃ P (0.7 g, 0.004 mol) into toluene 120 mL was reacted by stirring at 100 ℃ for 6 hours. After completion of the reaction, after extraction and concentration, 12.7 g of <Intermediate 3-173-2> was obtained by column and recrystallization (yield: 63.4%).

(3) manufacturing example 3: Synthesis of compound 3-173

(2-Phenyl-1,3-benzothiazol-6-yl)boronic acid (10.0 g, 0.039 mol), intermediate 3-173-2 (26.7 g, 0.047 mol), K ₂ CO ₃ (16.3 g, 0.118 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to Pd(PPh ₃ ) ₄ (0.9 g, 0.001 mol), followed by stirring at 100 °C for 6 hours. After completion of the reaction, 20.3 g (yield 74.3%) of <Compound 3-173> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=696 [(M+1) ⁺ ]

synthesis example 20: synthesis of compound 3-211

(One) manufacturing example 1: synthesis of intermediate 3-211-1

4-Bromodibenzofuran (10.0 g, 0.041 mol), 2-Amino-9,9-dimethylfluorene (12.7 g, 0.061 mol), NaO ^t Bu (7.8 g, 0.081 mol), Pd(dba) ₂ (1.2 g, 0.002 mol) ), t-Bu ₃ P (0.8 g, 0.004 mol) into toluene 120 mL was reacted by stirring at 100 ℃ for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columnized to obtain 11.0 g (yield: 72.4%) of <Intermediate 3-211-1>.

(2) manufacturing example 2: synthesis of intermediate 3-211-2

Dibromo-p-terphenyl (10.0 g, 0.026 mol), intermediate 3-211-1 (14.5 g, 0.039 mol), NaOtBu (5.0 g, 0.052 mol), Pd(dba) ₂ (0.7 g, 0.001 mol), t 120 mL of toluene was added to -Bu ₃ P (0.5 g, 0.003 mol), followed by stirring at 100 °C for 6 hours. After completion of the reaction, 6.4 g (yield: 36.4%) of <Intermediate 3-211-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) manufacturing example 3: Synthesis of compound 3-211

(2-Phenyl-1,3-benzothiazol-6-yl)boronic acid (10.0 g, 0.039 mol), intermediate 3-211-2 (32.1 g, 0.047 mol), K ₂ CO ₃ (16.3 g, 0.118 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to Pd(PPh ₃ ) ₄ (0.9 g, 0.001 mol), followed by stirring at 100 °C for 6 hours. After completion of the reaction, 25.7 g (yield 80.6%) of <Compound 3-211> was obtained by extracting and concentrating, followed by column and recrystallization.

LC/MS: m/z=812 [(M+1) ⁺ ]

device Example (HOST)

In an embodiment according to the present invention, the ITO transparent electrode was patterned to have a light emitting area of 2 mm × 2 mm using a glass substrate having a 25 mm × 25 mm × 0.7 mm ITO transparent electrode attached thereto, and then washed. After mounting the substrate in a vacuum chamber, the base pressure was set to 1 × 10 ⁻⁶ torr or more, and organic materials and metals were deposited on the ITO substrate in the following structure.

device Example 1 to 20

A red organic light emitting device having the following device structure was prepared by mixing the first host compound and the second host compound according to the present invention described in [Table 1] at a ratio of 6:4 and using them as the host compound of the light emitting layer, thereby increasing the current efficiency. The luminescent properties, including

ITO / hole injection layer (HAT-CN 5 nm) / hole transport layer (α-NPB 50 nm) / electron blocking layer (EB1 10 nm) / light emitting layer (40 nm) / electron transport layer (ET1:Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

[HAT-CN] was formed to a thickness of 5 nm to form a hole injection layer on the ITO transparent electrode, and then a hole transport layer was formed to a thickness of 50 nm using [α-NPB]. The hole blocking layer was deposited to a thickness of 10 nm using [EB1]. In addition, as the host of the light emitting layer, a mixture obtained by mixing the compound according to the present invention (first host compound: second host compound) in a ratio of 6:4 was used as described in [Table 1], and Ir(piq) ₂ ( acac) was doped and co-deposited to a thickness of 40 nm. In addition, a 30 nm film of an electron transport layer (the following [ET1] compound Liq 50% doped) was formed, LiF was deposited to a thickness of 1 nm as an electron injection layer, and then an Al film of 100 nm was formed to manufacture an organic light emitting device.

device comparative example One

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner as in the device structure of Examples 1 to 20, except that the following [RH1] was used alone as a host instead of the compound according to the present invention as a host material for the light emitting layer.

device comparative example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner as the device structure of Examples 1 to 20, except that the following [RH2] was used alone as a host instead of the compound according to the present invention as a host material for the light emitting layer.

device comparative example 3

The organic light emitting device for Device Comparative Example 3 is a mixture of [RH3] and a compound represented by [Chemical Formula 2] according to the present invention as a host material of the light emitting layer in the device structure of Examples 1 to 20, except that it is used as a host. and made identically.

device comparative example 4

The organic light emitting device for Device Comparative Example 4 is a mixture of [RH3] and a compound represented by [Chemical Formula 3] according to the present invention as a host material of the light emitting layer in the device structure of Examples 1 to 20, except that it is used as a host. and made identically.

device comparative example 5

The organic light emitting device for Device Comparative Example 5 is a host material of the light emitting layer in the device structure of Examples 1 to 20, except that a compound represented by [Formula 1] according to the present invention and [RH4] are mixed and used as a host. made identically.

Experimental example 1: element Example Luminescence characteristics of 1 to 20

Driving voltage, current efficiency and color coordinates were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) for the organic light emitting device manufactured according to the above Examples and Comparative Examples, 1,000 nit The standard result values are shown in [Table 1] below.

Example [Formula 1]
first host [Formula 2]
2nd host [Formula 3]
2nd host V cd/A CIEx CIEy One Formula 1-1 Formula 2-3 - 2.98 32.85 0.674 0.326 2 Formula 1-38 Formula 2-5 - 2.97 33.56 0.672 0.325 3 Formula 1-58 Formula 2-17 - 3.15 32.32 0.673 0.328 4 Formula 1-75 Formula 2-51 - 3.12 32.32 0.672 0.328 5 Formula 1-132 Formula 2-63 - 3.03 31.12 0.667 0.334 6 Formula 1-171 Formula 2-80 - 3.05 31.22 0.671 0.330 7 Formula 1-189 Formula 2-87 - 3.07 30.21 0.669 0.330 8 Formula 1-190 Formula 2-90 - 3.10 29.71 0.672 0.328 9 Formula 1-196 Formula 2-105 - 3.08 30.25 0.671 0.329 10 Formula 1-210 Formula 2-148 - 3.06 31.29 0.674 0.326 11 Formula 1-227 - Formula 3-2 3.07 31.35 0.673 0.326 12 Formula 1-235 - Formula 3-5 3.05 29.51 0.672 0.327 13 Formula 1-254 - Formula 3-16 3.03 30.52 0.671 0.329 14 Formula 1-268 - Formula 3-44 3.04 30.11 0.668 0.332 15 Formula 1-273 - Formula 3-98 3.07 29.35 0.671 0.329 16 Formula 1-281 - Formula 3-126 3.12 29.76 0.672 0.326 17 Formula 1-301 - Formula 3-159 3.15 30.55 0.669 0.333 18 Formula 1-313 - Formula 3-173 3.16 31.71 0.668 0.332 19 Formula 1-324 - Formula 3-211 3.18 29.56 0.672 0.327 20 Formula 1-339 - Formula 3-301 3.03 30.47 0.672 0.327 Comparative Example 1 RH1 - 4.42 9.12 0.657 0.338 Comparative Example 2 RH2 - 3.18 21.45 0.672 0.329 Comparative Example 3 RH3 Formula 2-3 - 3.25 22.67 0.675 0.329 Comparative Example 4 RH3 - Formula 3-16 3.38 24.31 0.673 0.327 Comparative Example 5 Formula 1-171 RH4 - 3.23 23.81 0.669 0.332

As can be seen in [Table 1], in the case of an organic light emitting device in which the compound according to the present invention is combined and used as a host material for the light emitting layer as a plurality of hosts, a device employing a conventional single compound as a host and the present invention Compared to the devices (Comparative Examples 1 to 5) employing a plurality of types of hosts without using the compound according to, it can be seen that the low-voltage drive characteristics and current efficiency of the device are remarkably excellent.

[HAT-CN] [α-NPB] [EB1] [RD1] [ET1]

[RH1] [RH2] [RH3] [RH4]

Claims (8)

A first host compound represented by the following [Formula 1]; And a plurality of host materials including a second host compound represented by the following [Formula 2] or [Formula 3]:
[Formula 1]

In the above [Formula 1],
Y is O or S, any one of A ₁ to A ₃ is represented by the following [Structural Formula 1], the others are hydrogen,
[Structural Formula 1]

In [Structural Formula 1],
L ₁ is a divalent linking group, and is any one selected from structures represented by the following [Structural Formula 2] (* indicates a portion connected to each other by a divalent linking group),
[Structural Formula 2]

X ₁ is each independently CH or N, and at least one or more of the plurality of Xs is N,
Ar ₁ to Ar ₂ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, It is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;

[Formula 2]

In the above [Formula 2],
L ₂ is a divalent linking group, and is any one selected from the following [Structural Formula 3] (* indicates a portion connected to each other by a divalent linking group);
[Structural Formula 3]

A ₄ is represented by the following [Structural Formula 4] (* indicates a portion connected to L ₂ ),
[Structural Formula 4]

In [Structural Formula 4],
X ₂ is O or S;
R ₁ to R ₄ are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, a cyano group, a halogen group, a hydroxy group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted C 1 group. 24 alkoxy group substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, substituted or unsubstituted arylsilyl group having 1 to 24 carbon atoms, substituted or unsubstituted It is selected from an aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,
L ₃ and L ₄ are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted carbazolylene group. , A substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted arylene group having 6 to 50 carbon atoms It is selected from a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms in which one or more cycloalkyls having 3 to 30 carbon atoms are fused (n and m are integers of 0 to 3, respectively, and when n and m are each 2 or more) A plurality of L ₃ and L ₄ are each the same as or different from each other),
Ar ₃ to Ar ₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms It is selected from substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms in which one or more ringed cycloalkyls having 3 to 30 carbon atoms are fused;

[Formula 3]

In the above [Formula 3],
L ₅ to L ₇ are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted carbazolylene group. , A substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted arylene group having 6 to 50 carbon atoms It is selected from substituted or unsubstituted heteroarylene groups having 2 to 50 carbon atoms in which one or more cycloalkyls having 3 to 30 carbon atoms are fused (o, p and q are each an integer of 0 to 3, wherein o, p and q are When each is 2 or more, a plurality of L ₅ to L ₇ are the same as or different from each other);
Ar ₅ to Ar ₆ are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms in which one or more substituted or unsubstituted cycloalkyls having 3 to 30 carbon atoms are fused, and a substituted or unsubstituted aryl group having 6 to 50 carbon atoms It is selected from substituted or unsubstituted heteroaryl groups having 2 to 50 carbon atoms in which one or more ringed cycloalkyls having 3 to 30 carbon atoms are fused,
X ₃ is O or S;
R is selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms. According to claim 1,
In the definition of L ₁ to L ₇ , Ar ₁ to Ar ₆ , R and R ₁ to R ₄ , 'substituted or unsubstituted' refers to deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a silyl group, In the group consisting of an alkyl group, a halogenated alkyl group, a deuterated alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group and an amine group A plurality of types of host materials, characterized in that they are substituted with selected one or two or more substituents, substituted with substituents in which two or more substituents among the substituents are connected, or have no substituents. According to claim 1,
[Formula 1] is a plurality of host materials, characterized in that any one selected from the following [Compound 1-1] to [Compound 1-342]:

According to claim 1,
[Formula 2] is a plurality of host materials, characterized in that any one selected from the following [Formula 2-1] to [Formula 2-151]:

According to claim 1,
[Formula 3] is a plurality of host materials, characterized in that any one selected from the following [Formula 3-1] to [Formula 3-389]:

An organic light emitting device comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode,
At least one of the organic layers includes a plurality of types of host materials according to claim 1, an organic light emitting device. According to claim 6,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection functions, an electron blocking layer, a hole blocking layer, and a light emitting layer. Including one or more floors,
An organic light emitting device comprising the plurality of host materials in the light emitting layer. According to claim 7,
An organic light emitting device in which the plurality of materials are mixed or laminated and used as a host material of the light emitting layer.