KR20220137294A - 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, which is employed in an organic layer such as an electron transport layer in an organic light emitting device to implement light emitting characteristics such as low voltage driving of the device and excellent light emitting efficiency, and to an organic light emitting device comprising 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.

In order to solve the above problems, the present invention provides an organic light emitting compound represented by the following [Formula I] and an organic light emitting device comprising the same.

[Formula Ⅰ]

The characteristic structure of the [Formula I] and the structures and definitions of the compounds implemented thereby, Y, 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] that can achieve luminescence characteristics such as low voltage driving and excellent luminous efficiency of the device of an organic light emitting device, and structurally a skeletal structure represented by the following [Formula I] That is, it is characterized by introducing a characteristic substituent through an L linkage into the structure of the indenoquinoline derivative, and through this structural characteristic, it is possible to improve the low voltage driving characteristics and the luminous efficiency characteristics of the organic light emitting diode.

[Formula Ⅰ]

In the above [Formula I],

Y is O, S or CR ₁ R ₂ , wherein R ₁ and R ₂ are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, or a substituted or unsubstituted C 3 to C 20 cycloalkyl group , a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 2 to C 30 heteroaryl group.

In addition, R ₁ and R ₂ may be combined with each other to form an alicyclic ring or an aromatic ring.

R is hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 1 to C 20 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C6 to C30 of an arylamine group, a substituted or unsubstituted C1 to C20 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, and a substituted or unsubstituted C1 to C20 alkoxy group, m is an integer of 0 to 4, and when m is 2 or more, a plurality of Rs are the same 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 [Structural Formula 1] or [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 and L ₂ are a single bond, or a substituted or unsubstituted C 6 to C 30 arylene group and a substituted or unsubstituted C 3 to C 30 heteroarylene group, n and o are each independently 0 to 3 is an integer, and when n and o are 2 or more, a plurality of L ₁ and L ₂ are the same as or different from each other, respectively.

Ar ₁ to Ar ₃ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, It is selected from a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 3 to C 30 heteroaryl group, p is an integer of 1 to 3, and when p is 2 or more, a plurality of Ar ₃ is same or different from each other

Meanwhile, in the definitions of R, R ₁ and R ₂ , L ₁ and L ₂ and Ar ₁ to Ar ₃ , 'substituted or unsubstituted' means R, R ₁ and R ₂ , L ₁ and L ₂ and Ar ₁ to Ar ₃ are each deuterium, a halogen group, a cyano group, a nitro group, a hydroxy 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 It is substituted with one or more substituents selected from the group consisting of an alkoxy group, an aryl group, a heteroaryl group, an alkylsilyl group and an arylsilyl group, or is substituted with a substituent to which two or more substituents are connected among the substituents, or does not have any substituents it means.

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 preferably 6 to 30, and also includes a polycyclic aryl group structure fused with cycloalkyl or the like, and a monocyclic aryl group Examples of the group include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a tetracenyl group, and a chrysenyl group. , a fluorenyl group, an acenaphthacenyl group, a triphenylene group, a fluoranthrene group, and the like, 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 is a polycyclic group in which cycloalkyl or heterocycloalkyl is fused. a heteroaryl group structure, and specific examples thereof in the present invention include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group , pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyridopyrazinyl group group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, There are dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, phenoxazine group, phenothiazine group, etc., but only these It is not limited.

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 receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. have. Specific examples of such conventional compounds 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 1

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

2-Fluorobenzeneboronic acid (10.0 g, 0.072 mol), 5-Bromo-2-chloro-6-methoxyquinoline (23.4 g, 0.086 mol), K ₂ CO ₃ (29.6 g, 0.214 mol), Pd(PPh ₃ ) ₄ ( Toluene 200 mL, EtOH 50 mL, and H ₂ O 50 mL) were added to 1.7 g, 0.001 mol), and the reaction was stirred at 100° C. for 6 hours. After completion of the reaction, 11.2 g (yield 54.5%) of <Intermediate 1-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 1-2

Intermediate 1-1 (10.0 g, 0.035 mol) was dissolved in anhydrous DCM, and BBr ₃ (in DCM) (21.8 g, 0.087 mol) was added dropwise at 0 °C dropwise. The reaction was stirred at room temperature for 16 hours. After completion of the reaction, 7.7 g (yield 81.0%) of <Intermediate 1-2> was obtained by extraction, concentration, and column.

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

Intermediate 1-2 (10.0 g, 0.037 mol), K ₂ CO ₃ (10.6 g, 0.077 mol) was put in 500 mL of NMP and reacted by stirring at 180 ° C. for 24 hours. After completion of the reaction, 4.8 g (yield 51.8%) of <Intermediate 1-3> was obtained by extraction, concentration, and column.

(4) production example 4: Synthesis of Intermediate 1-4

4-(4-Bromophenyl)-2,6-diphenylpyridine (10.0 g, 0.026 mol), Bis(pinacolato)diboron (7.9 g, 0.031 mol), KOAc (7.6 g, 0.078 mol), Pd(dppf)Cl ₂ ( 0.9 g, 0.001 mol) was added to 200 mL of dioxane and stirred at 100 °C for 12 hours to react. After completion of the reaction, 8.2 g (yield 73.1%) of <Intermediate 1-4> was obtained by extraction and concentration, followed by column and recrystallization.

(5) production example 5: Synthesis of compound 1

Intermediate 1-3 (10.0 g, 0.039 mol), Intermediate 1-4 (20.5 g, 0.047 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 1> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=524 [(M+1) ⁺ ]

Synthesis example 2: Synthesis of compound 10

(One) production example 1: Synthesis of Intermediate 10-1

Intermediate 1-3 (10.0 g, 0.039 mol), 1,4-Phenylenebisboronic acid (7.8 g, 0.047 mol), K ₂ CO ₃ (16.3 g, 0.118 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.008 mol) ), 140 mL of Toluene, 35 mL of EtOH, and 35 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, 8.2 g (yield 61.3%) of <Intermediate 10-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 10

Intermediate 10-1 (10.0 g, 0.030 mol), 2-Chloro-4,6-bis(4-phenylphenyl)-1,3,5-triazine (14.9 g, 0.035 mol), K ₂ CO ₃ (12.2 g, 0.089 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.006 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, 15.1 g (yield 75.5%) of <Compound 10> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=678 [(M+1) ⁺ ]

Synthesis example 3: Synthesis of compound 18

(One) production example 1: Synthesis of Intermediate 18-1

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, 0.006 mol) Toluene 140 mL, EtOH 35 mL, H ₂ O 35 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 18-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 18

Intermediate 10-1 (10.0 g, 0.030 mol), Intermediate 18-1 (18.1 g, 0.035 mol), K ₂ CO ₃ (12.2 g, 0.089 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.006 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, 16.8 g (yield 74.1%) of <Compound 18> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=768[(M+1) ⁺ ]

Synthesis example 4: Synthesis of compound 32

(One) production example 1: Synthesis of Intermediate 32-1

Cyanuric chloride (10.0 g, 0.054 mol), [4-(1,3-Benzoxazol-2-yl)phenyl]boronic acid (31.1 g, 0.130 mol), K ₂ CO ₃ (45.0 g, 0.325 mol), Pd ( Toluene 140 mL, EtOH 35 mL, and H ₂ O 35 mL were added to PPh ₃ ) ₄ (1.3 g, 0.001 mol) and stirred at 100° C. for 6 hours to react. After completion of the reaction, 16.2 g (yield 59.5%) of <Intermediate 32-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 32

Intermediate 10-1 (10.0 g, 0.030 mol), Intermediate 32-1 (17.8 g, 0.035 mol), K ₂ CO ₃ (12.2 g, 0.0006 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.006 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, 16.2 g (yield 72.2%) of <Compound 32> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=760[(M+1) ⁺ ]

Synthesis example 5: Synthesis of compound 51

(One) production example 1: Synthesis of intermediate 51-1

2,4-Dichloro-6-(4-phenylphenyl)-1,3,5-triazine (10.0 g, 0.033 mol), 9,9-Dimethyl-2-fluoreneboronic 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) 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, 9.2 g (yield 60.4%) of <Intermediate 51-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 51-2

Intermediate 1-3 (10 g, 0.021 mol), 4,4'-Biphenyldiyldiboronic acid (7.89 g, 0.046 mol), K ₂ CO ₃ (16.3 g, 0.118 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.0008 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, 11.2 g (yield 68.4%) of <Intermediate 51-1> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 51

Intermediate 51-2 (10.0 g, 0.024 mol), Intermediate 51-1 (13.3 g, 0.029 mol), K ₂ CO ₃ (9.9 g, 0.072 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.3 g (yield 69.5%) of <Compound 51>.

LC/MS: m/z=794 [(M+1) ⁺ ]

Synthesis example 6: Synthesis of compound 86

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

2-Methylsulfinylphenylboronic acid (10.0 g, 0.024 mol), 5-Bromo-2-chloroquinoline (13.3 g, 0.029 mol), K ₂ CO ₃ (9.9 g, 0.072 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005) mol) was added 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and the mixture was reacted by stirring under reflux at 100 °C for 6 hours. After completion of the reaction, 13.3 g (yield 69.5%) of <Intermediate 86-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of Intermediate 86-2

Intermediate 86-1 (10.0 g, 0.033 mol) and triflic acid (74.6 g, 0.497 mol) were stirred at room temperature for 24 hours. After that, 970 mL of pyridineH ₂ O (pyridine: H ₂ O = 1:1) was slowly added dropwise and stirred for 30 minutes to react. After completion of the reaction, 5.8 g (yield 64.9%) of <Intermediate 86-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of Intermediate 86-3

Intermediate 86-2 (10 g, 0.037 mol), 1,4-Phenylenebisboronic acid (7.4 g, 0.045 mol), K ₂ CO ₃ (15.4 g, 0.111 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.0007 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 8.7 g (yield 66.1%) of <Intermediate 86-3>.

(4) production example 4: Synthesis of intermediate 86-4

2-[1,1-Biphenyl]-4-yl-4,6-dichloro-1,3,5-triazine (10 g, 0.033 mol), Dibenzo[b,d]furan-3-ylboronic acid (8.4 g , 0.040 mol), K ₂ CO ₃ (13.7 g, 0.099 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) Add 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O to 100 for 6 hours. The reaction was stirred at ℃. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.1 g (yield 63.3%) of <Intermediate 86-4>.

(5) production example 5: Synthesis of compound 86

Intermediate 86-3 (10.0 g, 0.028 mol), Intermediate 86-4 (14.7 g, 0.034 mol), K ₂ CO ₃ (11.7 g, 0.085 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0006 mol) to 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, 13.6 g (yield 68.2%) of <Compound 86> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=708[(M+1) ⁺ ]

Synthesis example 7: Synthesis of compound 90

(One) production example 1: Synthesis of Intermediate 90-1

2-[1,1-Biphenyl]-4-yl-4,6-dichloro-1,3,5-triazine (10.0 g, 0.033 mol), (9-Phenyl-9H-carbazol-4-yl)boronic acid (11.4 g, 0.040 mol), K ₂ CO ₃ (13.7 g, 0.099 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) Add 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O 6 The reaction was stirred at 100 °C for a period of time. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.5 g (yield 56.4%) of <Intermediate 90-1>.

(2) production example 2: Synthesis of compound 90

Intermediate 86-3 (10.0 g, 0.028 mol), Intermediate 90-1 (17.2 g, 0.034 mol), K ₂ CO ₃ (11.7 g, 0.085 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 15.8 g (yield 71.6%) of <Compound 90> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=783[(M+1) ⁺ ]

Synthesis example 8: Synthesis of compound 91

(One) production example 1: Synthesis of intermediate 91-1

Intermediate 86-2 (10 g, 0.037 mol), 1,3-Phenylenediboronic acid (7.4 g, 0.045 mol), K ₂ CO ₃ (15.4 g, 0.111 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.0007 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.1 g (yield 61.5%) of <Intermediate 91-1>.

(2) production example 2: Synthesis of compound 91

Intermediate 91-1 (10.0 g, 0.028 mol), 2-(Biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (11.6 g, 0.034 mol), K ₂ CO ₃ ( 11.7 g, 0.085 mol), Pd(PPh ₃ ) ₄ (0.7 g, 0.0006 mol) was added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.8 g (yield 73.5%) of <Compound 91>.

LC/MS: m/z=618[(M+1) ⁺ ]

Synthesis example 9: Synthesis of compound 150

(One) production example 1: Synthesis of intermediate 150-1

4,6-Dibromodibenzofuran (10.0 g, 0.056 mol), 5-Bromo-2-chloroquinoline (16.2 g, 0.067 mol), K ₂ CO ₃ (23.0 g, 0.167 mol), Pd(PPh ₃ ) ₄ (1.3 g, 0.001 mol) was added 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, 12.2 g (yield 73.7%) of <Intermediate 150-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 150-2

A solution of intermediate 150-1 (10.0 g, 0.034 mol) in 150 mL of THF was added dropwise to 200 mL of MeMgBr (1.4 M in THF) dropwise for 3 hours so that the reaction temperature did not exceed 20 °C. After cooling at room temperature for 1 hour, 200 g of 10% Aqueous ammonium chloride and 300 mL of Toluene were added, and the reaction was stirred at room temperature for 1 hour. After completion of the reaction, 7.4 g (yield 74.0%) of <Intermediate 150-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of intermediate 150-3

Intermediate 150-2 (10.0 g, 0.034 mol) was put into 150 mL of AcOH and stirred at 0 °C for 30 minutes, then 300 mL of H ₃ PO ₄ was added, and the reaction was stirred at room temperature for 1 hour. After completion of the reaction, 5.3 g (yield 60.7%) of <Intermediate 150-3> was obtained by extraction and concentration, followed by column and recrystallization.

(4) production example 4: Synthesis of compound 150

Intermediate 150-3 (10.0 g, 0.036 mol), 4-(4,6-Diphenyl-1,3,5-triazin-2-yl)phenylboronic acid (15.2 g, 0.043 mol), K ₂ CO ₃ (14.8 g , 0.107 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added to 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 13.3 g (yield 67.3%) of <Compound 150>.

LC/MS: m/z=552 [(M+1) ⁺ ]

Synthesis example 10: Synthesis of compound 233

(One) production example 1: Synthesis of intermediate 233-1

5-Bromo-2-chloroquinoline (10.0 g, 0.041 mol), Bis(pinacolato)diboron (12.6 g, 0.050 mol), KOAc (12.1 g, 0.124 mol), Pd(dppf)Cl ₂ (1.5 g, 0.002 mol) 200 mL of dioxane was added, and the reaction was stirred at 100 °C for 12 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 8.3 g (yield 69.5%) of <Intermediate 233-1>.

(2) production example 2: Synthesis of intermediate 233-2

2-Bromobenzoic acid (10.0 g, 0.049 mol), intermediate 233-1 (17.3 g, 0.060 mol), K ₂ CO ₃ (20.6 g, 0.149 mol), Pd(PPh ₃ ) ₄ (1.2 g, 0.001 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted, concentrated, and then columned to obtain 9.5 g (yield 67.3%) of <Intermediate 233-2>.

(3) production example 3: Synthesis of intermediate 233-3

A solution of 100 mL of Triflic acid dissolved in Intermediate 233-2 (10 g, 0.038 mol) was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 8.8 g (yield 68.0%) of <Intermediate 233-3>.

(4) production example 4: Synthesis of intermediate 233-4

A solution of intermediate 233-3 (10 g, 0.038 mol) in 100 mL of THF is cooled to -78 °C. After that, 45.2 mL of PhMgBr (1.0 M in THF) is added dropwise over 3 hours. When the dropwise addition is completed, the mixture is stirred at room temperature for 12 hours. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 8.8 g (yield 68.0%) of <Intermediate 233-4>.

(5) production example 5: Synthesis of intermediate 233-5

Dissolve intermediate 233-4 (10.0 g, 0.029 mol), Benzene (33.2 g, 0.425 mol), and 100 mL of DCM. After that, triflic acid (61.5 g, 0.410 mol) was added, and the reaction was stirred at room temperature for 4 hours. After completion of the reaction, the mixture was extracted and concentrated, and then columned to obtain 8.1 g (yield 69.0%) of <Intermediate 233-5>.

(6) production example 6: Synthesis of intermediate 233-6

Intermediate 233-5 (10 g, 0.025 mol), 1,4-Phenylenebisboronic acid (4.9 g, 0.030 mol), K ₂ CO ₃ (10.3 g, 0.074 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, the mixture was extracted and concentrated, and then columned to obtain 8.7 g (yield 71.8%) of <Intermediate 233-6>.

(7) production example 7: Synthesis of intermediate 233-7

Cyanuric chloride (10.0 g, 0.054 mol), 4-Cyanobenzeneboronic acid (19.1 g, 0.130 mol), K ₂ CO ₃ (45.0 g, 0.325 mol), Pd(PPh ₃ ) ₄ (1.3 g, 0.001 mol) toluene 200 mL, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.2 g (yield 59.2%) of <Intermediate 233-7>.

(8) production example 8: Synthesis of compound 233

Intermediate 233-6 (10.0 g, 0.020 mol), Intermediate 233-7 (7.8 g, 0.025 mol), K ₂ CO ₃ (8.5 g, 0.061 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 mol) 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.1 g (yield 68.0%) of <Compound 233>.

LC/MS: m/z=726[(M+1) ⁺ ]

Synthesis example 11: Synthesis of compound 250

(One) production example 1: Synthesis of compound 250

Intermediate 233-6 (10.0 g, 0.020 mol), 3,3'-(5-Bromo-1,3-phenylene)dipyridine (7.6 g, 0.025 mol), K ₂ CO ₃ (8.5 g, 0.061 mol), Pd 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added to (PPh ₃ ) ₄ (0.5 g, 0.0004 mol), and the reaction was stirred at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.5 g (yield 76.0%) of <Compound 250>.

LC/MS: m/z=675[(M+1) ⁺ ]

Synthesis example 12: Synthesis of compound 261

(One) production example 1: Synthesis of Intermediate 261-1

Intermediate 233-5 (10 g, 0.025 mol), Naphthalene-1,4-diboronic acid (6.4 g, 0.030 mol), K ₂ CO ₃ (10.3 g, 0.074 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) was added 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.2 g (yield 76.4%) of <Intermediate 261-1>.

(2) production example 2: Synthesis of compound 261

Intermediate 261-1 (10.0 g, 0.019 mol), 2-Chloro-4,6-diphenyltriazine (6.0 g, 0.022 mol), K ₂ CO ₃ (7.7 g, 0.056 mol), Pd(PPh ₃ ) ₄ (0.4 g , 0.0004 mol) was added 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 8.9 g (yield 66.0%) of <Compound 261>.

LC/MS: m/z=726[(M+1) ⁺ ]

Synthesis example 13: Synthesis of compound 275

(One) production example 1: Synthesis of intermediate 275-1

2-Bromo-1-iodobenzene (10.0 g, 0.035 mol), Intermediate 233-1 (12.3 g, 0.042 mol), K ₂ CO ₃ (14.7 g, 0.106 mol), Pd(PPh ₃ ) ₄ (0.8 g, 0.0007 mol) was added 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, and stirred at 100 °C for 6 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 6.7 g (yield: 59.5%) of <Intermediate 275-1>.

(2) production example 2: Synthesis of intermediate 275-2

Intermediate 275-1 (10.0 g, 0.031 mol) and 100 mL of THF were dissolved at -78 °C, and n-BuLi (4.0 g, 0.063 mol) was added thereto and stirred for 1 hour. After that, it was added to a solution of 9H-Fluorene-9-one (in THF, 5.7 g, 0.031 mol) cooled to -78 °C and reacted for 1 hour. Upon completion of the reaction, the mixture was raised to room temperature, extracted, concentrated, and columned to obtain 9.5 g (yield 72.1%) of <Intermediate 275-2>.

(3) production example 3: Synthesis of intermediate 275-3

Intermediate 275-2 (10.0 g, 0.024 mol) was dissolved in 100 mL of AcOH and stirred for 1 hour. Then, after raising to room temperature, 100 mL of HCl was added, and the reaction was stirred for 2 hours. After completion of the reaction, extraction and concentration were performed to obtain 7.2 g (yield 75.2%) of <Intermediate 275-3>.

(4) production example 4: Synthesis of intermediate 275-4

Intermediate 275-3 (10 g, 0.025 mol), 1,4-Phenylenediboronic acid (5.0 g, 0.030 mol), K ₂ CO ₃ (10.3 g, 0.075 mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol) ), 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 7.9 g (yield 65.2%) of <Intermediate 275-4>.

(5) production example 5: Synthesis of compound 275

Intermediate 275-4 (10.0 g, 0.021 mol), 2-Chloro-4,6-bis(4-phenylphenyl)-1,3,5-triazine (10.3 g, 0.025 mol), K ₂ CO ₃ (8.5 g, 0.062 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 mol) was added with 200 mL of toluene, 50 mL of ethanol, and 50 mL of H ₂ O, followed by stirring at 100 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.8 g (yield 63.7%) of <Compound 275>.

LC/MS: m/z=826[(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 and the base pressure was set to 1 × 10 ^-6 torr or more, the organic material and the metal were deposited on the ITO in the following structure.

device Example 1 to 70

By using the compound implemented according to the present invention as an electron transport layer, 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 except that the following [ET1] was used instead of the compound according to the present invention for the electron transport layer in the device structures of Examples 1 to 70.

device comparative example 2

The organic light emitting device for Device Comparative Example 2 was manufactured in the same manner except that the following [ET2] was used instead of the compound according to the present invention for the electron transport layer in the device structures of Examples 1 to 70.

device comparative example 3

The organic light emitting device for Device Comparative Example 3 was manufactured in the same manner as in Examples 1 to 70, except that the following [ET3] was used instead of the compound according to the present invention for the electron transport layer.

Experimental example 1: element Example 1 to 70 luminescent properties

The organic electroluminescent 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 is shown in [Table 1] below.

Example electron transport layer V cd/A CIEx CIEy One Formula 1 4.1 7.5 0.133 0.153 2 Formula 2 3.7 7.4 0.131 0.154 3 Formula 3 3.5 7.7 0.134 0.152 4 Formula 4 3.6 7.5 0.132 0.153 5 Formula 6 3.8 7.3 0.133 0.150 6 Formula 7 3.9 7.3 0.134 0.151 7 Formula 9 3.7 7.7 0.133 0.154 8 Formula 10 4.0 7.7 0.133 0.153 9 Formula 12 3.8 7.4 0.134 0.155 10 Formula 14 3.9 7.7 0.131 0.155 11 Formula 15 3.8 7.5 0.133 0.150 12 Formula 17 3.8 7.6 0.130 0.154 13 Formula 18 3.5 7.7 0.133 0.153 14 Formula 19 4.1 7.2 0.134 0.158 15 Formula 24 3.8 7.2 0.132 0.151 16 Formula 30 3.7 7.5 0.134 0.150 17 Formula 32 3.6 8.1 0.133 0.155 18 Formula 36 3.9 7.3 0.132 0.151 19 Formula 39 3.6 7.5 0.135 0.154 20 Formula 43 3.6 7.3 0.132 0.153 21 Formula 47 3.7 7.8 0.133 0.154 22 Formula 51 3.8 7.7 0.132 0.151 23 Formula 63 4.0 7.3 0.134 0.152 24 Formula 76 3.6 7.5 0.133 0.152 25 Formula 77 3.9 7.7 0.135 0.154 26 Formula 78 3.8 8.0 0.134 0.150 27 Formula 86 4.0 7.3 0.131 0.153 28 Formula 89 3.6 7.4 0.134 0.150 29 Formula 90 3.8 7.3 0.133 0.153 30 Formula 91 4.0 7.5 0.134 0.151 31 Formula 92 3.7 7.5 0.134 0.150 32 Formula 113 3.8 7.4 0.131 0.149 33 Formula 120 3.7 7.9 0.130 0.152 34 Formula 121 3.8 7.2 0.132 0.155 35 Formula 122 3.6 7.5 0.133 0.153 36 Formula 131 3.5 7.6 0.133 0.154 37 Formula 133 3.6 7.2 0.131 0.151 38 Formula 134 3.8 7.4 0.132 0.152 39 Formula 135 3.6 7.3 0.132 0.155 40 Formula 139 3.9 7.7 0.133 0.153 41 Formula 150 3.9 7.9 0.134 0.150 42 Formula 152 3.7 7.5 0.131 0.155 43 Formula 153 3.6 7.6 0.138 0.148 44 Formula 157 3.8 7.4 0.135 0.151 45 Formula 160 3.9 7.5 0.132 0.158 46 Formula 162 3.8 7.5 0.135 0.153 47 Formula 163 3.6 7.2 0.134 0.151 48 Formula 170 3.9 7.3 0.132 0.155 49 Formula 187 3.9 7.3 0.133 0.153 50 Formula 188 3.7 7.7 0.134 0.154 51 Formula 189 3.8 7.9 0.132 0.151 52 Formula 190 3.7 7.5 0.134 0.158 53 Formula 191 3.7 7.9 0.136 0.156 54 Formula 200 3.6 7.4 0.134 0.157 55 Formula 208 3.9 7.7 0.137 0.155 56 Formula 209 3.5 7.5 0.135 0.156 57 Formula 217 3.7 7.3 0.136 0.153 58 Formula 219 3.8 7.3 0.137 0.154 59 Formula 221 4.0 7.2 0.137 0.151 60 Formula 225 3.9 7.7 0.136 0.156 61 Formula 229 3.9 7.6 0.134 0.156 62 Formula 230 3.7 7.4 0.135 0.156 63 Formula 233 3.8 7.7 0.134 0.158 64 Formula 235 3.7 7.9 0.131 0.149 65 Formula 243 3.7 7.5 0.136 0.153 66 Formula 244 3.8 7.8 0.136 0.157 67 Formula 250 3.4 7.7 0.135 0.156 68 Formula 261 3.7 7.6 0.133 0.157 69 Formula 265 3.7 7.2 0.135 0.154 70 Formula 275 3.6 7.5 0.137 0.153 Comparative Example 1 ET1 4.6 6.8 0.134 0.149 Comparative Example 2 ET2 4.7 6.5 0.136 0.149 Comparative Example 3 ET3 4.5 7.0 0.135 0.145

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 to 3).

[HAT_CN] [α-NPB] [BH1] [BD1] [EBL1]

[ET1] [ET2] [ET3]

Claims (6)

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

In the [Formula I],
Y is O, S or CR ₁ R ₂ ,
Wherein R ₁ and R ₂ are each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, or substituted or unsubstituted C 6 to C 30 aryl Any one selected from a group and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
The R ₁ and R ₂ may be combined with each other to form an alicyclic ring or an aromatic ring,
R is hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, a substituted or unsubstituted C 1 to C 20 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C1 to C20 alkylamine group, a substituted or unsubstituted C6 to C30 Any one selected from an arylamine group, a substituted or unsubstituted C1-C20 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group and a substituted or unsubstituted C1-C20 alkoxy group ego,
m is an integer of 0 to 4, and when m is 2 or more, a plurality of Rs are the same as 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] or [Structural Formula 2],
X _One To X ₃ Are the same as or different from each other, each independently CH or N,
L ₁ and L ₂ are 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,
n and o are each independently an integer of 0 to 3, and when n and o are each 2 or more, a plurality of L ₁ and L ₂ are the same as or different from each other,
Ar ₁ to Ar ₃ are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, 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 of 1 to 3, and when p is 2 or more, a plurality of Ar ₃ are the same as or different from each other. According to claim 1,
In the definitions of R, R ₁ and R ₂ , L and Ar ₁ to Ar ₂ , 'substituted or unsubstituted' means that R, R ₁ and R ₂ , L and Ar ₁ To Ar ₂ are deuterium, Halogen group, cyano group, nitro group, hydroxyl group, alkyl group, halogenated alkyl group, deuterated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, deuterated alkoxy group, aryl group, heteroaryl group, An organic light-emitting compound, characterized in that it is substituted with one or two or more substituents selected from the group consisting of an alkylsilyl group and an arylsilyl 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 309]:

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. 5. The method of claim 4,
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]. 6. The method of claim 5,
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.