KR20220136613A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound represented by a chemical formula I that is employed in an organic layer such as an electron transport layer in an organic light emitting device to realize light emitting characteristics such as low voltage driving, excellent light emitting efficiency and the like of the device, and to an organic light emitting device including the same.

Description

An organic light emitting compound and an organic light emitting device comprising the same

The present invention relates to an organic light emitting compound, and more particularly, to an organic light emitting compound, characterized in that it is employed as an organic layer material in an organic light emitting device, and an organic light emitting property having significantly improved light emitting properties such as low voltage driving and excellent luminous efficiency of the device by employing the same It relates to a light emitting device.

The organic light emitting device can be formed on a transparent substrate as well as being able to drive at a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescence (EL) display, and consume relatively little power. , has the advantage of excellent color, and can represent three colors of green, blue, and red, and has recently become a subject of much interest as a next-generation display device.

However, in order for such an organic light emitting device to exhibit the above characteristics, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. However, the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed.

Therefore, in order to realize a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, additional improvements are required in terms of efficiency and lifespan characteristics. It is desperately needed.

Accordingly, an object of the present invention is to provide a novel organic light emitting compound capable of implementing excellent light emitting characteristics such as low voltage driving and improved luminous efficiency of the device by being employed in the organic layer in the organic light emitting device, and an organic light emitting device including the same.

The present invention provides an organic light emitting compound represented by the following [Formula I] in order to solve the above problems.

[Formula Ⅰ]

The characteristic structure of the [Formula I] and the compounds implemented thereby, X, L and A will be described later.

When the organic light emitting compound according to the present invention is employed as a material for an organic layer such as an electron transport layer in an organic light emitting device, it is possible to realize light emitting characteristics such as low voltage driving and excellent luminous efficiency of the device, so it can be usefully used in various display devices.

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

The present invention relates to an organic light-emitting compound represented by the following [Formula I], which can achieve light-emitting characteristics such as low voltage driving of the organic light-emitting device and excellent light-emitting efficiency,

It is characterized in that a characteristic substituent A is introduced through a linking group (L) into the skeletal structure structurally represented by the following [Formula I], that is, at least one oxazoloquinoline, thiazoloquinoline, or mimidazoquinoline derivative, and these structural features are Through this, it is possible to improve the low voltage driving characteristics and luminous efficiency characteristics of the organic light emitting diode.

[Formula Ⅰ]

In the above [Formula I],

X is O, S or NR ₁ , wherein R ₁ is hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, substituted or an unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group.

L is a single bond, or any one selected from a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group, m is an integer from 0 to 3, wherein m In the case of two or more, a plurality of L's are the same as or different from each other.

A is characterized in that it is represented by the following [Structural Formula 1] or [Structural Formula 2].

[Structural Formula 1]

[Structural Formula 2]

In the above [Structural Formula 1] and [Structural Formula 2],

X ₁ to X ₃ are the same as or different from each other, and each independently is CH or N.

L ₁ is a single bond, or is selected from a substituted or unsubstituted C6 to C30 arylene group and a substituted or unsubstituted C3 to C30 heteroarylene group, o is an integer from 0 to 3, wherein o is 2 In the case of more than one, a plurality of L ₁ are the same as or different from each other.

Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently selected from hydrogen, 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, q and r is an integer of 0 to 3, and when q and r are each 2 or more, the plurality of Ar ₁ and Ar ₂ are the same as or different from each other, respectively.

Ar ₃ 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, p is an integer from 0 to 3, and when p is 2 or more, the plurality of Ar ₃ is the same as or different from each other.

n is an integer of 1 to 3, and when n is 2 or more, the structures in the plurality of parentheses [ ] are the same or different from each other.

l is an integer of 1 to 2, and when l is 2, each A is the same as or different from each other.

According to an embodiment of the present invention, the [Formula I] may be any one selected from the following [Formula I-1] to [Formula I-4].

[Formula Ⅰ-1] [Formula Ⅰ-2]

[Formula Ⅰ-3] [Formula Ⅰ-4]

In the [Formula I-1] to [Formula I-4], the definitions of X, L, A, n and m are the same as the definitions in the [Formula I].

On the other hand, in the definition of R ₁ , L, L ₁ and Ar ₁ to Ar ₃ , 'substituted or unsubstituted' means that R ₁ , L, L ₁ and Ar ₁ to Ar ₃ are deuterium and halogen, respectively. group, cyano group, nitro group, hydroxyl group, silyl group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, aryl group and heteroaryl It means that it is substituted with one or two or more substituents selected from the group consisting of a group, is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.

For specific examples, the 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, etc. 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 a condensed heterocyclic group thereof, such as a benzquinoline group. , 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 the present invention is not limited thereto.

In the present invention, the alkyl group may be linear 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 alkoxy group may be straight-chain or branched. Although the number of carbon atoms of the alkoxy group is not particularly limited, it 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 , a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

In the present invention, a deuterated alkyl group or alkoxy group, halogenated alkyl group or alkoxy group means an alkyl group or alkoxy group in which the alkyl group 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, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.

,

,

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

,

,

etc.

,

등이 있다.In the present invention, the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in 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 addition, the fluorenyl group represented as described above may be further condensed with an alicyclic or aromatic ring on each benzene ring.

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, and a specific example thereof in the present invention is 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 Zol group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadia and 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 the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxy phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but is not limited thereto.

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

In the present invention, the cycloalkyl group refers to, and includes, monocyclic, polycyclic and spiro alkyl radicals, preferably containing 3 to 20 ring carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirodecyl, adamantyl, and the like, wherein the cycloalkyl group may be optionally substituted.

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

The organic light emitting compound according to the present invention represented by the [Formula I] can be used as various organic layers, including the electron transport layer in the organic light emitting device due to its structural specificity.

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

As such, the organic light emitting compound according to the present invention can synthesize an organic light emitting compound having various characteristics by using a characteristic skeleton exhibiting intrinsic properties and a moiety having intrinsic properties introduced thereto, As a result, the organic light emitting compound according to the present invention can be applied to various organic layer materials such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. can be further improved.

In addition, the compound of the present invention can be applied to a device according to a general organic light emitting device manufacturing method.

The 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. Except that, it may be manufactured using conventional device manufacturing methods and materials.

The organic layer of the organic light emitting diode according to the present invention may have a single layer structure, but may have a multilayer 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, a hole blocking layer, etc., a structure including a light efficiency improving layer (Capping layer) provided in the organic light emitting device It may have, but is not limited thereto, and may include a smaller number or a larger number of organic layers.

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

In addition, the organic light emitting diode according to the present invention is a metal or conductive metal oxide or an alloy thereof on a substrate by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be prepared 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 diode 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 in a smaller number by a solvent process rather than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

As the anode material, a material having a large 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, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. 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) , a conductive polymer such as polypyrrole and polyaniline, but is not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode 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 and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is 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 material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, 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 is suitable, and a material having high hole mobility is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. can be further improved.

The light-emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having 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, benzoxazole, benzthiazole and There are benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but is not limited thereto.

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

The organic light emitting diode according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

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

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, the scope of the present invention is not limited thereby, and it is common in the art that various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those with knowledge.

Synthesis example 1: Synthesis of compound 3

(One) production example 1: Synthesis of Intermediate 3-1

Add 7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), and 200 mL of DMF, and stir at 80 °C for 2 hours. reacted. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 14.3 g (yield 70.4%) of <Intermediate 3-1>.

(2) production example 2: Synthesis of compound 3

Intermediate 3-1 (10.0 g, 0.031 mol), 10-Phenylanthracene-9-boronic acid (11.0 g, 0.037 mol), K ₂ CO ₃ (12.8 g, 0.092 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 11.3 g (yield 73.7%) of <Compound 3> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=498 [(M+1) ⁺ ]

Synthesis example 2: Synthesis of compound 13

(One) production example 1: Synthesis of Intermediate 13-1

Intermediate 3-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Pd(dppf)Cl ₂ (1.1 g, 0.002 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.2 g (yield 71.6%) of <Intermediate 13-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 13

Intermediate 3-1 (10.0 g, 0.027 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (8.6 g, 0.032 mol), K ₂ CO ₃ (11.1 g, 0.081 mol), Pd (PPh ₃ ) ₄ (0.6 g, 0.0005 mol) was added to 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 9.1 g (yield 70.9%) of <Compound 13> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=477 [(M+1) ⁺ ]

Synthesis example 3: Synthesis of compound 19

(One) production example 1: Synthesis of Intermediate 19-1

2-Chloro-4,6-diphenyl-1,3,5-triazine (10 g, 0.044 mol), 4-Cyanobenzeneboronic acid (7.8 g, 0.053 mol), K ₂ CO ₃ (18.3 g, 0.133 mol), Pd 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O were added to (PPh ₃ ) ₄ (1.0 g, 0.0009 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, 7.2 g (yield 55.6%) of <Intermediate 19-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 19

Intermediate 13-1 (10.0 g, 0.027 mol), Intermediate 19-1 (9.4 g, 0.032 mol), K ₂ CO ₃ (11.1 g, 0.081 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 200 mL, EtOH 50 mL, H ₂ O 50 mL, and stirred at 100 ℃ for 6 hours to react. After completion of the reaction, 9.7 g (yield 71.9%) of <Compound 19> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=502[(M+1) ⁺ ]

Synthesis example 4: Synthesis of compound 25

(One) production example 1: Synthesis of Intermediate 25-1

2,4-Dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (10.0 g, 0.029 mol), (4-Naphthalen-2-ylphenyl)boronic acid (8.7 g, 0.035 mol), K ₂ CO ₃ (12.1 g, 0.088 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 200 mL, EtOH 50 mL, H ₂ O 50 mL Add 6 hours The reaction was stirred at 100 °C for a while. After completion of the reaction, 7.7 g (yield 51.7%) of <Intermediate 25-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 25

Intermediate 13-1 (10.0 g, 0.027 mol), Intermediate 25-1 (16.4 g, 0.032 mol), K ₂ CO ₃ (11.1 g, 0.081 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 200 mL, EtOH 50 mL, H ₂ O 50 mL, and stirred at 100 ℃ for 6 hours to react. After completion of the reaction, 13.3 g (yield 68.8%) of <Compound 25> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=719[(M+1) ⁺ ]

Synthesis example 5: Synthesis of compound 41

(One) production example 1: Synthesis of compound 41

Dissolve 7-Amino-8-hydroxyquinoline (7.9 g, 0.049 mol) and 25.7 mL of Triethylamine in NMP. Then, 1,4-Benzenedicarbonyl chloride (10.0 g, 0.049 mol) was added dropwise at room temperature and reacted at 160 °C for 24 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 6.3 g (yield 30.9%) of <Compound 41>.

LC/MS: m/z=414 [(M+1) ⁺ ]

Synthesis example 6: Synthesis of compound 44

(One) production example 1: Synthesis of intermediate 44-1

1-Bromo-4-iodonaphthalene (10.0 g, 0.030 mol), 4-Cyanobenzeneboronic acid (5.3 g, 0.036 mol), K ₂ CO ₃ (12.5 g, 0.090 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006) mol) into 200 mL of Toluene, 50 mL of EtOH, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 5.6 g (yield 60.5%) of <Intermediate 44-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 44

Intermediate 13-1 (10.0 g, 0.027 mol), Intermediate 44-1 (9.9 g, 0.032 mol), K ₂ CO ₃ (11.1 g, 0.081 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 200 mL, EtOH 50 mL, H ₂ O 50 mL, and stirred at 100 ℃ for 6 hours to react. After completion of the reaction, 9.5 g (yield 74.7%) of <Compound 44> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=473 [(M+1) ⁺ ]

Synthesis example 7: Synthesis of compound 50

(One) production example 1: Synthesis of intermediate 50-1

7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromo-1-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), 200 mL of DMF, and 2 The reaction was stirred for an hour. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 16.6 g (yield 70.9%) of <Intermediate 50-1>.

(2) production example 2: Synthesis of intermediate 50-2

Intermediate 50-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), dioxane 200 in Pd(dppf)Cl ₂ (1.0 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.3 g (yield 73.8%) of <Intermediate 50-2>.

(3) production example 3: Synthesis of compound 50

Intermediate 50-2 (10.0 g, 0.024 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (7.6 g, 0.028 mol), K ₂ CO ₃ (9.8 g, 0.071 mol), Pd (PPh ₃ ) ₄ (0.6 g, 0.0005 mol) was put into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 9.8 g (yield 78.4%) of <Compound 50> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=527[(M+1) ⁺ ]

Synthesis example 8: Synthesis of compound 53

(One) production example 1: Synthesis of compound 53

Dissolve 7-Amino-8-hydroxyquinoline (6.0 g, 0.038 mol) and 25.7 mL of Triethylamine in NMP. Then, 1,3,5-Benzenetricarboxylic chloride (10.0 g, 0.038 mol) was added dropwise at room temperature and reacted at 160 °C for 24 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.2 g (yield 32.8%) of <Compound 53>.

LC/MS: m/z=582[(M+1) ⁺ ]

Synthesis example 9: Synthesis of compound 69

(One) production example 1: Synthesis of Intermediate 69-1

7-Amino-8-hydroxyquinoline (10.0 g, 0.062 mol), 2-Bromo-1-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), 200 mL of DMF, and 2 The reaction was stirred for an hour. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 15.8 g (yield 67.5%) of <Intermediate 69-1>.

(2) production example 2: Synthesis of intermediate 69-2

Intermediate 69-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), dioxane 200 in Pd(dppf)Cl ₂ (1.0 g, 0.001 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.5 g (yield 75.5%) of <Intermediate 69-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 69

Intermediate 69-2 (10.0 g, 0.024 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (7.6 g, 0.028 mol), K ₂ CO ₃ (9.8 g, 0.071 mol), Pd (PPh ₃ ) ₄ (0.6 g, 0.0005 mol) was put into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 7.1 g (yield 56.8%) of <Compound 69> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=527[(M+1) ⁺ ]

Synthesis example 10: synthesis of compound 73

(One) production example 1: Synthesis of Intermediate 73-1

Add 8-Amino-7-hydroxyquinoline (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), and 200 mL of DMF, and stir at 80 °C for 2 hours. reacted. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.9 g (yield 68.5%) of <Intermediate 73-1>.

(2) production example 2: Synthesis of compound 73

Intermediate 73-1 (10.0 g, 0.031 mol), 10-(2-Naphthenyl)anthracene-9-boric acid (12.9 g, 0.037 mol), K ₂ CO ₃ (12.8 g, 0.092 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) was added to 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 11.5 g (yield 68.2%) of <Compound 73> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=548[(M+1) ⁺ ]

Synthesis example 11: Synthesis of compound 86

(One) production example 1: Synthesis of Intermediate 86-1

Intermediate 73-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), dioxane 200 in Pd(dppf)Cl ₂ (1.1 g, 0.002 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.8 g (yield 68.1%) of <Intermediate 86-1>.

(2) production example 2: Synthesis of compound 86

Intermediate 86-1 (10.0 g, 0.027 mol), 2,4-Bis([1,1'-biphenyl]-3-yl)-6-chloro-1,3,5-triazine (13.5 g, 0.032 mol) , K ₂ CO ₃ (11.1 g, 0.081 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) into Toluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and stirred at 100 ° C for 6 hours to react did it After completion of the reaction, 12.2 g (yield 72.1%) of <Compound 86> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=629 [(M+1) ⁺ ]

Synthesis example 12: Synthesis of compound 98

(One) production example 1: Synthesis of intermediate 98-1

Cyanuric chloride (10.0 g, 0.054 mol), 4-(2-Benzo[d]oxazolyl)phenylboronicacid (31.1 g, 0.130 mol), K ₂ CO ₃ (45.0 g, 0.325 mol), Pd(PPh ₃ ) ₄ (1.3 g, 0.001 mol) into 140 ml of Toluene, 35 ml of EtOH, and 35 ml of H ₂ O, followed by stirring at 100° C. for 6 hours to react. After completion of the reaction, 17.2 g (yield 63.2%) of <Intermediate 98-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 98

Intermediate 86-1 (10.0 g, 0.027 mol), Intermediate 98-1 (16.2 g, 0.032 mol), K ₂ CO ₃ (11.1 g, 0.081 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 13.1 g (yield 68.5%) of <Compound 98> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=711 [(M+1) ⁺ ]

Synthesis example 13: Synthesis of compound 107

(One) production example 1: Synthesis of intermediate 107-1

8-Amino-7-hydroxyquinoline (10.0 g, 0.062 mol), 2-Bromo-6-naphthaldehyde (14.7 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), 200 mL of DMF, and 2 The reaction was stirred for an hour. After completion of the reaction, 16.8 g (yield 71.7%) of <Intermediate 107-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 107-2

Intermediate 107-1 (10.0 g, 0.027 mol), Bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.9 g, 0.080 mol), Pd(dppf)Cl ₂ (1.0 g, 0.001 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.2 g (yield 72.9%) of <Intermediate 107-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 107

Intermediate 107-1 (10.0 g, 0.027 mol), Intermediate 107-2 (13.5 g, 0.032 mol), K ₂ CO ₃ (11.1 g, 0.080 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) Toluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 11.8 g (yield 75.0%) of <Compound 107> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=590[(M+1) ⁺ ]

Synthesis example 14: Synthesis of compound 115

(One) production example 1: Synthesis of compound 115

2,4-Dichloro-6-(4-phenylphenyl)-1,3,5-triazine (10.0 g, 0.033 mol), intermediate 98-2 (29.6 g, 0.079 mol), K ₂ CO ₃ (27.4 g, 0.199) mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added with 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 17.5 g (yield 73.3%) of <Compound 115> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=721 [(M+1) ⁺ ]

Synthesis example 15: Synthesis of compound 124

(One) production example 1: Synthesis of Intermediate 124-1

2,4-Dichloro-6-(9,9-dimethyl-9H-fluoren-2-yl)-1,3,5-triazine (10.0 g, 0.029 mol), 9,9'-Spirobi(9H-fluorene) Toluene 140 mL, EtOH 35 mL, H ₂ O in -2-boronic acid (12.6 g, 0.035 mol), K ₂ CO ₃ (12.1 g, 0.088 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) 35 mL was added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, 8.8 g (yield 48.4%) of <Intermediate 124-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 124

To Intermediate 124-1 (10.0 g, 0.029 mol), Intermediate 98-2 (12.6 g, 0.035 mol), K ₂ CO ₃ (12.1 g, 0.088 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) Toluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 11.4 g (yield 68.2%) of <Compound 124> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=830 [(M+1) ⁺ ]

Synthesis example 16: Synthesis of compound 131

(One) production example 1: Synthesis of intermediate 131-1

Add 7-Amino-6-quinolinol (10.0 g, 0.062 mol), 4-Bromobenzenealdehyde (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), and 200 mL of DMF, and stir at 80 °C for 2 hours. reacted. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 13.2 g (yield: 65.0%) of <Intermediate 131-1>.

(2) production example 2: Synthesis of intermediate 131-2

Intermediate 131-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), Pd(dppf)Cl ₂ (1.1 g, 0.002 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 7.7 g (yield 67.3%) of <Intermediate 131-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 131

Intermediate 131-2 (10.0 g, 0.027 mol), 4-Chloro-2,6-diphenylpyridine (8.6 g, 0.032 mol), K ₂ CO ₃ (11.1 g, 0.081 mol), Pd(PPh ₃ ) ₄ (0.6 g , 0.0005 mol) into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 9.2 g (yield 72.0%) of <Compound 131> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=475[(M+1) ⁺ ]

Synthesis example 17: Synthesis of compound 133

(One) production example 1: Synthesis of Intermediate 133-1

7-Amino-6-quinolinol (10.0 g, 0.062 mol), 3',5'-Dibromo[1,1'-biphenyl]-4-carboxaldehyde (21.2 g, 0.062 mol), p-Toluenesulfonic acid (2.1 g, 0.013 mol), 200 mL of DMF was added, and the reaction was stirred at 80 °C for 2 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 20.1 g (yield: 67.1%) of <Intermediate 133-1>.

(2) production example 2: Synthesis of compound 133

Intermediate 133-1 (10.0 g, 0.021 mol), 4-(pyridin-3-yl)phenylboronic acid (10.0 g, 0.050 mol), K ₂ CO ₃ (17.3 g, 0.125 mol), Pd(PPh ₃ ) ₄ ( 0.5 g, 0.0004 mol) into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, 9.8 g (yield 74.8%) of <Compound 133> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=628[(M+1) ⁺ ]

Synthesis example 18: Synthesis of compound 190

(One) production example 1: Synthesis of intermediate 190-1

7-Amino-6-quinolinol (10.0 g, 0.062 mol), 3-Formyl-1-bromobenzene (11.6 g, 0.062 mol), p-Toluenesulfonic acid (2.2 g, 0.013 mol), 200 mL of DMF, and 2 The reaction was stirred for an hour. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.8 g (yield 63.1%) of <Intermediate 190-1>.

(2) production example 2: Synthesis of intermediate 190-2

Intermediate 190-1 (10.0 g, 0.031 mol), Bis(pinacolato)diboron (9.4 g, 0.037 mol), KOAc (9.1 g, 0.092 mol), dioxane 200 in Pd(dppf)Cl ₂ (1.1 g, 0.002 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.1 g (yield 70.8%) of <Intermediate 190-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 190

Intermediate 190-2 (10.0 g, 0.027 mol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (8.6 g, 0.032 mol), K ₂ CO ₃ (11.1 g, 0.081 mol), Pd (PPh ₃ ) ₄ (0.6 g, 0.0005 mol) was put into 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O, followed by stirring at 100° C. for 6 hours. After completion of the reaction, 15.3 g (yield 74.0%) of <Compound 190> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=477 [(M+1) ⁺ ]

Synthesis example 19: Synthesis of compound 337

(One) production example 1: Synthesis of intermediate 337-1

7-Bromo-8-nitroquinoline (10.0 g, 0.040 mol), Aniline (5.5 g, 0.059 mol), NaOtBu (7.6 g, 0.079 mol), Pd(dba) ₂ (1.1 g, 0.002 mol), t-Bu ₃ 150 mL of toluene was added to P (0.8 g, 0.004 mol), and the reaction was stirred at 70 °C for 4 hours. After completion of the reaction, 7.7 g (yield 73.5%) of <Intermediate 337-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 337-2

Intermediate 337-1 (10.0 g, 0.038 mol), Pd/C (12.0 g, 0.113 mol) was slowly added dropwise to Hydrazine hydrate (45.7 g, 1.425 mol) and stirred for 1 hour to react. After completion of the reaction, 7.5 g (yield 84.6%) of <Intermediate 337-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 337-3

Intermediate 337-2 (10.0 g, 0.043 mol), 4-bromobenzaldehyde (7.9 g, 0.043 mol), p-Toluenesulfonic acid (1.5 g, 0.009 mol), 200 mL of DMF was added, and the reaction was stirred at 80 °C for 2 hours. After completion of the reaction, 11.8 g (yield 69.4%) of <Intermediate 337-3> was obtained by extraction and concentration by column.

(4) production example 4: Synthesis of intermediate 337-4

Intermediate 337-3 (10.0 g, 0.025 mol), Bis(pinacolato)diboron (7.6 g, 0.030 mol), KOAc (7.4 g, 0.075 mol), Pd(dppf)Cl ₂ (0.9 g, 0.001 mol) dioxane 200 mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.3 g (yield 74.3%) of <Intermediate 337-4> was obtained by extraction and concentration by column.

(5) production example 5: Synthesis of intermediate 337-5

2,4-Dichloro-6-(4-phenylphenyl)-1,3,5-triazine (10.0 g, 0.033 mol), (9,9-Dimethyl-9H-fluoren-2-yl)boronic acid (9.5 g, 0.040 mol), K ₂ CO ₃ (13.7 g, 0.099 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) in oluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and at 100 °C for 6 hours The reaction was stirred. After completion of the reaction, 8.1 g (yield 53.2%) of <Intermediate 337-5> was obtained by extraction and concentration, followed by column and recrystallization.

(6) production example 6: Synthesis of compound 337

Intermediate 337-4 (10.0 g, 0.015 mol), Intermediate 337-5 (4.3 g, 0.018 mol), K ₂ CO ₃ (16.3 g, 0.118 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.0008 mol) Toluene 140 mL, EtOH 35 mL, H ₂ O 35 mL, and stirred for 6 hours at 100 ℃ reacted. After completion of the reaction, 15.3 g (yield 74.0%) of <Compound 337> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=744[(M+1) ⁺ ]

device Example ( ETL )

In an embodiment according to the present invention, the ITO transparent electrode is patterned so that the light emitting area is 2 mm × 2 mm on a glass substrate of 25 mm × 25 mm × 0.7 mm, using an ITO glass substrate to which an ITO transparent electrode is attached. and then washed. After the substrate was mounted in a vacuum chamber, the base pressure was set to 1 × 10 ^-6 torr or more, and the organic material and the metal were deposited on the ITO in the following structure.

device Example 1 to 83

The compound implemented according to the present invention was used as an electron transport layer material, and an organic light emitting device having the following device structure was fabricated, and then light emission and driving characteristics of the compound implemented according to the present invention were measured.

ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (EBL1 10 nm) / light emitting layer (20 nm) / electron transport layer (201: Liq, 30 nm) / LiF (1 nm) / Al (100 nm)

To form a hole injection layer on the ITO transparent electrode, [HAT-CN] was used to deposit a thickness of 5 nm, and then the hole transport layer was deposited at 100 nm using α-NPB. The electron blocking layer was deposited to a thickness of 10 nm using [EBL1]. In addition, [BH1] was used as the host compound for the light emitting layer, and the dopant compound was co-deposited to a thickness of 20 nm using [BD1], and the electron transport layer was a compound according to the present invention as shown in [Table 1] below. After 30 nm (Liq doping) deposition using Thereafter, Al was deposited to a thickness of 100 nm to fabricate an organic light emitting diode.

device comparative example One

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner as in the device structures of Examples 1 to 83, except that the following [ET1] was used instead of the compound according to the present invention as the electron transport layer material.

device comparative example 2

The organic light emitting device for Device Comparative Example 2 was prepared in the same manner as in the device structures of Examples 1 to 83, except that the following [ET2] was used instead of the compound according to the present invention as the electron transport layer material.

Experimental example 1: element Example 1 to 83 luminescent properties

The organic light emitting device manufactured according to the above example was measured for voltage, current and luminous efficiency using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), and the result value based on 1000 nit was It is shown in [Table 1] below.

Example electron transport layer V cd/A CIEx CIEy One Formula 1 3.9 7.7 0.132 0.147 2 Formula 2 3.8 8.1 0.134 0.148 3 Formula 3 4.1 7.4 0.132 0.148 4 Formula 5 3.9 7.7 0.132 0.147 5 Formula 9 3.7 7.8 0.129 0.153 6 Formula 13 3.7 7.7 0.130 0.150 7 Formula 14 3.6 7.8 0.133 0.145 8 Formula 17 3.6 7.6 0.131 0.149 9 Formula 19 4.1 7.6 0.134 0.145 10 Formula 20 3.8 7.7 0.133 0.146 11 Formula 21 3.9 7.5 0.132 0.147 12 Formula 22 3.9 7.9 0.131 0.150 13 Formula 23 4.0 7.7 0.132 0.148 14 Formula 24 3.7 7.5 0.133 0.145 15 Formula 25 4.1 7.4 0.133 0.150 16 Formula 27 3.8 7.7 0.133 0.146 17 Formula 29 4.1 7.5 0.133 0.146 18 Formula 30 4.1 7.2 0.131 0.149 19 Formula 33 4.0 7.5 0.133 0.147 20 Formula 35 4.0 7.5 0.136 0.144 21 Formula 41 3.9 7.3 0.132 0.148 22 Formula 43 3.9 7.3 0.131 0.147 23 Formula 44 4.0 7.5 0.131 0.150 24 Formula 49 4.1 7.7 0.130 0.150 25 Formula 50 4.0 7.4 0.132 0.148 26 Formula 53 3.8 7.8 0.131 0.145 27 chemical formula 57 3.9 7.5 0.132 0.146 28 Formula 61 3.8 7.3 0.131 0.142 29 Formula 62 4.0 7.8 0.130 0.145 30 Formula 67 3.9 7.5 0.131 0.146 31 Formula 68 3.8 7.9 0.130 0.145 32 Formula 69 4.1 7.2 0.130 0.145 33 Formula 73 3.9 7.5 0.130 0.145 34 Formula 79 3.7 7.8 0.137 0.150 35 Formula 80 3.8 7.5 0.138 0.147 36 Formula 84 3.7 7.5 0.131 0.142 37 Formula 86 3.7 7.4 0.135 0.146 38 Formula 88 4.2 7.2 0.132 0.142 39 Formula 91 3.9 7.5 0.131 0.143 40 Formula 92 4.0 7.5 0.130 0.144 41 Formula 93 3.9 7.7 0.139 0.147 42 Formula 94 3.7 7.9 0.130 0.145 43 Formula 98 4.0 7.4 0.131 0.142 44 Formula 99 4.1 7.5 0.131 0.147 45 Formula 100 3.6 7.9 0.131 0.143 46 Formula 101 4.0 7.5 0.131 0.143 47 Formula 106 4.0 7.4 0.129 0.146 48 Formula 107 3.9 7.6 0.130 0.145 49 Formula 110 3.9 7.7 0.134 0.146 50 Formula 112 4.0 7.5 0.131 0.145 51 Formula 115 3.9 7.5 0.129 0.144 52 Formula 124 4.0 7.6 0.129 0.147 53 Formula 125 4.1 7.9 0.128 0.147 54 Formula 131 4.0 7.4 0.132 0.148 55 Formula 133 4.0 7.3 0.131 0.148 56 Formula 137 4.0 7.5 0.134 0.149 57 Formula 139 3.8 7.3 0.133 0.145 58 Formula 141 3.9 7.8 0.132 0.148 59 Formula 142 3.8 7.5 0.132 0.144 60 Formula 143 3.7 7.9 0.130 0.145 61 Formula 144 4.0 7.2 0.130 0.145 62 Formula 187 3.8 7.5 0.135 0.149 63 Formula 189 3.7 7.5 0.137 0.150 64 Formula 190 3.7 7.5 0.138 0.147 65 Formula 212 3.6 7.7 0.131 0.142 66 Formula 229 3.6 7.6 0.139 0.146 67 Formula 233 4.1 7.6 0.132 0.142 68 Formula 237 3.8 7.7 0.131 0.143 69 Formula 242 3.9 7.7 0.130 0.144 70 Formula 247 4.0 7.9 0.139 0.147 71 Formula 255 4.1 7.6 0.130 0.145 72 Formula 267 3.8 7.4 0.131 0.142 73 Formula 279 4.2 7.5 0.131 0.147 74 Formula 289 4.2 7.9 0.131 0.143 75 Formula 293 4.0 7.7 0.136 0.145 76 Formula 318 4.0 7.2 0.138 0.146 77 Formula 336 3.9 7.5 0.130 0.142 78 Formula 337 3.9 7.5 0.133 0.145 79 Formula 342 4.0 7.2 0.132 0.148 80 Formula 345 4.1 7.3 0.131 0.147 81 Formula 348 3.9 7.5 0.133 0.150 82 Formula 354 4.2 7.7 0.130 0.150 83 Formula 355 4.1 7.4 0.132 0.148 Comparative Example 1 ET1 4.7 6.6 0.135 0.151 Comparative Example 2 ET2 4.6 6.5 0.138 0.156

Looking at the results shown in [Table 1], when the compound according to the present invention is applied to a device as an electron transport layer material, the compound used as the conventional electron transport material and the compound in contrast to the characteristic structure of the compound according to the present invention, respectively It can be seen that the light-emitting properties such as low voltage driving characteristics, light-emitting efficiency, and quantum efficiency are significantly superior to those of the employed devices (Comparative Examples 1 and 2).

[HAT_CN] [α-NPB] [BH1] [BD1] [EBL1]

[ET1] [ET2]

Claims (7)

An organic light emitting compound represented by the following [Formula I]:
[Formula Ⅰ]

In the [Formula I],
X is O, S or NR ₁ ,
Wherein R ₁ is hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl Any one selected from a group and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,
L is a single bond, or any one selected from a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group,
m is an integer from 0 to 3, and when m is 2 or more, a plurality of L's are the same or different from each other,
A is represented by the following [Structural Formula 1] or [Structural Formula 2],
[Structural Formula 1]

[Structural Formula 2]

In the [Structural Formula 1] and [Structural Formula 2],
X _One To X ₃ Are the same as or different from each other, each independently CH or N,
L ₁ is a single bond, or any one selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms,
o is an integer of 0 to 3, and when o is 2 or more, a plurality of L ₁ are the same as or different from each other,
Ar ₁ and Ar ₂ are the same as or different from each other and are each independently selected from hydrogen, 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,
q and r are integers of 0 to 3, and when q and r are each 2 or more, the plurality of Ar ₁ and Ar ₂ are the same as or different from each other,
Ar ₃ is any one selected from a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group,
p is an integer from 0 to 3, and when p is 2 or more, the plurality of Ar ₃ are the same as or different from each other,
n is an integer of 1 to 3, and when n is 2 or more, the structures in the plurality of parentheses [ ] are the same or different from each other,
l is an integer of 1 to 2, and when l is 2, each A is the same as or different from each other. According to claim 1,
The [Formula I] is an organic light emitting compound which is any one selected from the following [Formula 1-1] to [Formula 1-4]:
[Formula Ⅰ-1] [Formula Ⅰ-2]

[Formula Ⅰ-3] [Formula Ⅰ-4]

In the [Formula I-1] to [Formula I-4], the definitions of X, L, A, n and m are the same as the definitions in the [Formula I]. According to claim 1,
In the definition of R ₁ , L, L ₁ and Ar ₁ to Ar ₃ , 'substituted or unsubstituted' means that R ₁ , L, L ₁ and Ar ₁ To Ar ₃ are deuterium, a halogen group, A cyano group, a nitro group, a hydroxyl group, a silyl group, an alkyl group, a halogenated alkyl group, a deuterated alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group and a heteroaryl group. An organic light-emitting compound, characterized in that it is substituted with one or two or more substituents selected from the group, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents. According to claim 1,
The [Formula I] is an organic light emitting compound, characterized in that any one selected from the following [Compound 1] to [Compound 360]:

An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
At least one of the organic layers is an organic light emitting device comprising the organic light emitting compound of [Formula I] according to claim 1. 6. The method of claim 5,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer and a light emitting layer including one or more floors that become
At least one of the layers comprises an organic light emitting compound represented by the [Formula I]. 7. The method of claim 6,
An organic light emitting device comprising an organic light emitting compound represented by the above [Formula I] in any one of the electron transport layer, the electron injection layer, and the layer performing both electron transport and electron injection functions.