KR20220010440A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by the following chemical formula I. When the organic light emitting compound of the present invention is employed as an electron transport layer compound in an organic light emitting device, an organic light emitting device that has better low voltage driving characteristics and superior quantum efficiency and luminous efficacy characteristics compared with conventional devices can be realized.

Description

An organic light emitting compound and an organic light emitting device comprising the same {An electroluminescent compound and an electroluminescent device comprising the same}

The present invention relates to an organic light emitting compound employed in an organic layer in an organic light emitting device and an organic light emitting device having significantly improved light emitting characteristics such as low voltage driving and excellent luminous efficiency of the device by employing the same.

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 light emitting (EL) display, and consume relatively little power. It has the advantage of excellent color and can display three colors of green, blue, and red.

However, in order for such an organic light emitting device to exhibit the above characteristics, the material constituting the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, and an electron injection material, is supported by stable and efficient materials. However, the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed. Therefore, the development of a new material capable of improving light emitting characteristics and development of an organic layer structure in a device are continuously required.

Accordingly, the present invention is to provide an organic light emitting compound and an organic light emitting device comprising the same, which can be employed in an organic layer such as an electron transport layer in an organic light emitting device to significantly improve various light emitting characteristics including low voltage driving characteristics and luminous efficiency of the device. .

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 structure and characteristic substituents of the [Formula I] and specific compounds implemented thereby will be described later.

The organic light emitting device employing the organic light emitting compound according to the present invention in the electron transport layer can realize excellent low voltage driving characteristics and remarkably improved luminous efficiency, and thus 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 characterized in that it is represented by the following [Formula I], and when it is employed as an electron transport material in an organic layer in the organic light emitting device, the implementation of an organic light emitting device having excellent quantum efficiency and light emitting efficiency It is possible.

[Formula Ⅰ]

In the [Formula I],

L 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, n is an integer from 0 to 3, wherein n is 2 In the case of more than one, a plurality of L's are the same or different from each other.

X _{One To} X _{3 Are} the same as or different from each other and each independently represent CH or N, provided that at least two or more of _{X One To} X _{3 is N.} That is, _{the structure including X 1} to X ₃ is characterized in that it is triazine or pyrimidine.

That is, the compound according to the present invention is structurally characterized in that a triazine derivative or a pyrimidine derivative is introduced through L at the 3-position of carbazole.

Ar ₁ to Ar ₂ are the same as or different from each other, and are each independently 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.

R ₁ is a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, substituted or unsubstituted A substituted or unsubstituted C 1 to C 20 alkoxy group, a substituted or unsubstituted C 1 to C 20 halogenated alkyl group, a substituted or unsubstituted C 1 to C 20 halogenated alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 3 to C 30 heteroaryl group.

That is, the compound according to the present invention is structurally characterized in that a phenyl group is introduced into the -N group of the carbazole, and a substituent R ₁ is further introduced at an ortho position.

Meanwhile, in the _{definition of L, Ar 1} to Ar ₂ and R ₁ , 'substituted or unsubstituted' means that L, Ar ₁ to Ar ₂ and R ₁ are deuterium, a halogen group, a cyano group, and a nitro group, respectively. , a hydroxy group, a silyl group, an alkyl group, a halogenated alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, an alkenyl group, an aryl group and a heteroaryl group substituted with one or two or more substituents selected from the group consisting of, or It means that two or more of the substituents are substituted with a linked substituent or do not have any substituents.

For specific examples, the substituted aryl group is a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a peryleneyl group, a tetracenyl group, an anthracenyl group, etc. means replaced.

The substituted heteroaryl group includes 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 benz It means that an imidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, etc. are substituted with one or more 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 in 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 phenyl group, biphenyl group, terphenyl group, stilbene group, etc., examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, 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 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. It includes 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, and preferably contains 3 to 20 carbon atoms in the ring, 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, or the like.

The organic light emitting compound according to the present invention represented by the [Formula I] may be used as an organic layer of an organic light emitting device due to its structural specificity, and more specifically, may be used as a material for an electron transport layer of the organic layer.

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

As such, the compound according to the present invention can synthesize an organic light emitting compound having various properties using a characteristic skeleton exhibiting intrinsic properties and a moiety having intrinsic properties introduced thereto, and 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. In particular, the compound of [Formula I] according to the present invention is used as an electron transport layer material Or, after designing the electron transport layer as a plurality of layers, when applied as a plurality of electron transport layers together with the conventional electron transport layer material, the luminous efficiency and lifespan characteristics of the device 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, and the organic light emitting device according to an embodiment of the present invention includes a first electrode and a second electrode and an organic layer disposed therebetween. and may be manufactured using conventional device manufacturing methods and materials, except that the organic light emitting compound according to the present invention is used in the organic layer of the device.

The organic layer of the organic light emitting device according to the present invention may have a single-layer structure, but may have a multi-layered 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 improvement layer (Capping layer) provided in the organic light emitting device 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.

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

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, but is not limited thereto, and may have a single layer structure. In addition, the organic layer can be formed in a smaller number by a solvent process rather than a vapor 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 multi-layered materials 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, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

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 Benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but are 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. Specifically, it may be an organic light emitting compound represented by [Formula I] according to the present invention, or an Al complex of 8-hydroxyquinoline _{, a complex including Alq 3} , an organic radical compound, a hydroxyflavone-metal complex, etc. . According to a preferred embodiment of the present invention, a plurality of layers comprising a second electron transport layer comprising the conventional electron transport material and a first electron transport layer comprising an organic light emitting compound represented by [Formula I] according to the present invention. can be designed

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

In addition, the organic light emitting compound according to the present invention can 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, synthesis examples and device examples of preferred compounds are presented to help the understanding of the present invention. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereby.

Synthesis example 1: Synthesis of compound 4

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

1-Bromo-2-fluorobenzene (10.0 g, 0.057 mol), 3,5-Di-tert-butylphenylboronic Acid (16.1 g, 0.069 mol), K ₂ CO ₃ (23.7 g, 0.171 mol), Pd(PPh ₃ ) ₄ (1.3 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, 11.3 g (yield 69.5%) of <Intermediate 4-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of intermediate 4-2

Add 500 mL of DMF to 3-Bromocarbazole (10.0 g, 0.041 mol), Intermediate 4-1 (13.9 g, 0.049 mol), Cs ₂ CO ₃ (8.4 g, 0.061 mol), and react by stirring under reflux at 150 ° C. for 12 hours. made it After completion of the reaction, extraction was performed, followed by concentration and column to obtain 14.8 g (yield 71.3%) of <Intermediate 4-2>.

(3) production example 3: Synthesis of intermediate 4-3

Intermediate 4-2 (10.0 g, 0.020 mol), bis(pinacolato)diboron (5.9 g, 0.024 mol), CH ₃ CO ₂ K (3.8 g, 0.039 mol), Pd(dppf)Cl ₂ (0.43 g, 0.0006 mol) ) into 200 mL of dioxane 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 8.2 g (yield 75.1%) of <Intermediate 4-3>.

(4) production example 4: Synthesis of compound 4

Intermediate 4-3 (10.0 g, 0.018 mol), 4-([1,1'-Biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine (7.4 g, 0.022 mol), K ₂ CO ₃ (7.4 g, 0.054 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0004 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, 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 9.8 g (yield 74.0%) of <Compound 4>.

LC/MS: m/z=737[(M) ⁺ ]

Synthesis example 2: Synthesis of compound 15

(One) production example 1: Synthesis of intermediate 15-1

500 mL of DMF was added to 3-Bromocarbazole (10.0 g, 0.041 mol), 2-Fluorobiphenyl (8.4 g, 0.049 mol), Cs ₂ CO ₃ (8.4 g, 0.061 mol), and the reaction was stirred under reflux at 150 ° C. for 12 hours. . After completion of the reaction, 11.4 g (yield 70.4%) of <Intermediate 15-1> was obtained by extraction and concentration by column.

(2) production example 2: Synthesis of intermediate 15-2

Intermediate 15-1 (10.0 g, 0.025 mol), bis(pinacolato)diboron (7.7 g, 0.030 mol), KOAc (4.9 g, 0.050 mol), _{dioxane 200 in Pd(dppf)Cl 2} (0.6 g, 0.0008 mol) mL and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed to obtain 8.2 g (yield 73.3%) of <Intermediate 15-2>.

(3) production example 3: Synthesis of intermediate 15-3

2,4,6-Trichloropyrimidine (10.0 g, 0.055 mol), (2-(tert-butyl)phenyl)boronic acid (23.3 g, 0.131 mol), K ₂ CO ₃ (45.2 g, 0.327 mol), Pd(PPh) ₃ ) ₄ (1.3 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, extraction and concentration were performed, followed by column and recrystallization to obtain 13.1 g (yield: 63.4%) of <Intermediate 15-3>.

(4) production example 4: Synthesis of compound 15

Intermediate 15-2 (10.0 g, 0.023 mol), Intermediate 15-3 (10.2 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 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 10.2 g (yield 68.6%) of <Compound 15>.

LC/MS: m/z=661 [(M) ⁺ ]

Synthesis example 3: Synthesis of compound 24

(One) production example 1: Synthesis of Intermediate 24-1

2,4,6-Trichloro-1,3,5-triazine (10.0 g, 0.054 mol), (2-(tert-Butyl)phenyl)boronic acid (23.2 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, ethanol 50 mL, H ₂ O 50 mL, 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 13.1 g (yield 63.6%) of <Intermediate 24-1>.

(2) production example 2: Synthesis of compound 24

Intermediate 15-2 (10.0 g, 0.023 mol), Intermediate 24-1 (10.2 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 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 10.8 g (yield 72.6%) of <Compound 24>.

LC/MS: m/z=662 [(M) ⁺ ]

Synthesis example 3: Synthesis of compound 31

(One) production example 1: Synthesis of intermediate 31-1

2,4,6-Trichloro-1,3,5-triazine (10.0 g, 0.054 mol), (2-(tert-Butyl)phenyl)boronic acid (23.2 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, ethanol 50 mL, H ₂ O 50 mL, 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 14.2 g (yield 68.9%) of <Intermediate 31-1>.

(2) production example 2: Synthesis of compound 31

Intermediate 15-2 (10.0 g, 0.023 mol), Intermediate 31-1 (10.2 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 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 10.2 g (yield 68.5%) of <Compound 31>.

LC/MS: m/z=662 [(M) ⁺ ]

Synthesis example 4: Synthesis of compound 55

(One) production example 1: Synthesis of compound 55

Intermediate 4-3 (10.0 g, 0.018 mol), 2-(4-Bromo-1-naphthalenyl)-4,6-diphenyl-1,3,5-triazine (9.4 g, 0.022 mol), K ₂ CO ₃ ( 7.4 g, 0.054 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0004 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, and reacted 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 9.1 g (yield 64.3%) of <Compound 55>.

LC/MS: m/z=789 [(M) ⁺ ]

Synthesis example 5: Synthesis of compound 70

(One) production example 1: Synthesis of intermediate 70-1

Intermediate 15-2 (10.0 g, 0.023 mol), 1-Bromo-2-iodobenzene (7.6 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004) mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, 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 6.8 g (yield: 63.8%) of <Intermediate 70-1>.

(2) production example 2: Synthesis of intermediate 70-2

Intermediate 70-1 (10.0 g, 0.021 mol), bis(pinacolato)diboron (6.4 g, 0.025 mol), CH ₃ CO ₂ K (6.2 g, 0.063 mol), Pd(dppf)Cl ₂ (0.8 g, 0.001 mol) ) into 200 mL of dioxane and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 7.5 g (yield 68.2%) of <Intermediate 70-2>.

(3) production example 3: Synthesis of compound 70

Intermediate 70-2 (10.0 g, 0.019 mol), Intermediate 24-1 (8.7 g, 0.023 mol), K ₂ CO ₃ (8.0 g, 0.058 mol), Pd(PPh ₃ ) ₄ (0.4 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, the mixture was extracted, concentrated, and columned to obtain 8.6 g (yield: 60.7%) of <Compound 70>.

LC/MS: m/z=738 [(M) ⁺ ]

Synthesis example 6: Synthesis of compound 84

(One) production example 1: Synthesis of Intermediate 84-1

Add 500 mL of DMF to 3-Bromocarbazole (10.0 g, 0.041 mol), 1-tert-Butyl-2-fluorobenzene (7.4 g, 0.049 mol), and Cs ₂ CO ₃ (8.4 g, 0.061 mol) at 150 ° C for 12 hours The reaction was stirred under reflux for a while. After completion of the reaction, extraction and concentration were performed, followed by column to obtain 9.5 g (yield 61.8%) of <Intermediate 84-1>.

(2) production example 2: Synthesis of Intermediate 84-2

Intermediate 84-1 (10.0 g, 0.026 mol), bis(pinacolato)diboron (8.1 g, 0.032 mol), KOAc (7.8 g, 0.079 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 to obtain 8.5 g (yield 75.6%) of <Intermediate 84-2>.

(3) production example 3: Synthesis of Intermediate 84-3

4,6-Dichloro-2-(3-chlorophenyl)-1,3,5-triazine (10.0 g, 0.038 mol), 4-tert-Butylphenylboronic acid (16.4 g, 0.092 mol), K ₂ CO ₃ (31.8 g , 0.230 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.0008 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, 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 12.5 g (yield 71.4%) of <Intermediate 84-3>.

(4) production example 4: Synthesis of compound 84

Intermediate 84-2 (10.0 g, 0.024 mol), Intermediate 84-3 (12.9 g, 0.028 mol), K ₂ CO ₃ (9.8 g, 0.071 mol), Pd(OAc) ₂ (1.4 g, 0.001 mol), X -Phos (1.1 g, 0.002 mol), 200 mL of THF and _{50 mL of H 2} O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 11.5 g (yield 68.0%) of <Compound 84>.

LC/MS: m/z=718 [(M) ⁺ ]

Synthesis example 7: Synthesis of compound 98

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

2,4-Dichloro-6-(4-chlorophenyl)-1,3,5-triazine (10.0 g, 0.038 mol), B-[4-(2-Benzoxazolyl)phenyl]boronic acid (22.0 g, 0.092 mol) , K ₂ CO ₃ (31.8 g, 0.230 mol), Pd(PPh ₃ ) ₄ (0.9 g, 0.0008 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, and stirred at 100 ° C for 6 hours. reacted. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 14.1 g (yield 63.6%) of <Intermediate 98-1>.

(2) production example 2: Synthesis of compound 98

Intermediate 4-3 (10.0 g, 0.018 mol), Intermediate 98-1 (12.4 g, 0.022 mol), K ₂ CO ₃ (7.4 g, 0.054 mol), Pd(OAc) ₂ (1.0 g, 0.001 mol), X -Phos (0.9 g, 0.002 mol), 200 mL of THF and _{50 mL of H 2} O were added, and the reaction was stirred at 90 °C for 6 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 10.9 g (yield: 62.5%) of <Compound 98>.

LC/MS: m/z=973 [(M) ⁺ ]

Synthesis example 8: Synthesis of compound 102

(One) production example 1: Synthesis of Intermediate 102-1

2-Bromofluorobenzene (10.0 g, 0.057 mol), 3,5-Bis(trifluoromethyl)benzeneboronic acid (17.7 g, 0.069 mol), K ₂ CO ₃ (23.7 g, 0.171 mol), Pd(PPh ₃ ) ₄ (1.3 g , 0.001 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, and stirred at 100 °C for 6 hours to react. After completion of the reaction, 10.8 g (yield 61.3%) of <Intermediate 102-1> was obtained by extraction and concentration by column.

(2) production example 2: Synthesis of Intermediate 102-2

Add 500 mL of DMF to 3-Bromocarbazole (10.0 g, 0.041 mol), Intermediate 102-1 (15.0 g, 0.049 mol), Cs ₂ CO ₃ (8.4 g, 0.061 mol), and react by stirring under reflux at 150 ° C for 12 hours. made it After completion of the reaction, 13.3 g (yield 61.3%) of <Intermediate 102-2> was obtained by extraction, concentration, and column.

(3) production example 3: Synthesis of Intermediate 102-3

Intermediate 102-2 (10.0 g, 0.019 mol), bis(pinacolato)diboron (5.7 g, 0.023 mol), CH ₃ CO ₂ K (5.5 g, 0.056 mol), Pd(dppf)Cl ₂ (0.7 g, 0.001 mol) ) into 200 mL of dioxane and stirred at 100 °C for 12 hours to react. After completion of the reaction, extraction and concentration were performed to obtain 7.9 g (yield 72.6%) of <Intermediate 102-3>.

(4) production example 4: Synthesis of intermediate 102-4

2,4-Dichloro-6-phenyl-1,3,5-triazine (10.0 g, 0.044 mol), 4-Biphenylboronic acid (10.5 g, 0.053 mol), K ₂ CO ₃ (18.3 g, 0.133 mol), Pd (PPh ₃ ) ₄ (1.0 g, 0.001 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL 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 8.2 g (yield 53.9%) of <Intermediate 102-4>.

(5) production example 5: Synthesis of compound 102

Intermediate 102-3 (10.0 g, 0.017 mol), Intermediate 102-4 (7.1 g, 0.021 mol), K ₂ CO ₃ (7.1 g, 0.052 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.003 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 9.8 g (yield 74.7%) of <Compound 102>.

LC/MS: m/z=762 [(M) ⁺ ]

Synthesis example 9: Synthesis of compound 111

(One) production example 1: Synthesis of intermediate 111-1

2,4,6-Trichloro-1,3,5-triazine (10.0 g, 0.054 mol), 2-Trifluoromethylbenzeneboronic acid (24.7 g, 0.130 mol), K ₂ CO ₃ (45.0 g, 0.325 mol), Pd(PPh) ₃ ) ₄ (1.3 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, extraction and concentration were performed, followed by column and recrystallization to obtain 14.8 g (yield 67.6%) of <Intermediate 111-1>.

(2) production example 2: Synthesis of compound 111

Intermediate 15-2 (10.0 g, 0.023 mol), Intermediate 111-1 (10.9 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 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 8.7 g (yield 56.4%) of <Compound 111>.

LC/MS: m/z=686 [(M) ⁺ ]

Synthesis example 10: Synthesis of compound 122

(One) production example 1: Synthesis of compound 122

Intermediate 102-3 (10.0 g, 0.017 mol), Intermediate 111-1 (8.3 g, 0.021 mol), K ₂ CO ₃ (7.1 g, 0.052 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0003 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 8.5 g (yield 60.1%) of <Compound 122>.

LC/MS: m/z=822 [(M) ⁺ ]

Synthesis example 11: Synthesis of compound 159

(One) production example 1: Synthesis of Intermediate 159-1

2,4-Dichloro-6-phenyl-1,3,5-triazine (10.0 g, 0.055 mol), 4-Cyanophenylboronic acid (19.2 g, 0.131 mol), K ₂ CO ₃ (45.2 g, 0.327 mol), Pd (PPh ₃ ) ₄ (1.3 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, extraction and concentration were performed, followed by column and recrystallization to obtain 11.3 g (yield 65.4%) of <Intermediate 159-1>.

(2) production example 2: Synthesis of compound 159

Intermediate 15-2 (10.0 g, 0.026 mol), Intermediate 159-1 (8.5 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 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 8.8 g (yield: 65.4%) of <Compound 159>.

LC/MS: m/z=599 [(M) ⁺ ]

Synthesis example 12: Synthesis of compound 269

(One) production example 1: Synthesis of compound 269

Intermediate 15-2 (10.0 g, 0.023 mol), 2-(2-Bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.5 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, 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 10.2 g (yield 72.5%) of <Compound 269>.

LC/MS: m/z=626 [(M) ⁺ ]

Synthesis example 13: Synthesis of compound 271

(One) production example 1: Synthesis of intermediate 271-1

2,4-Dichloro-6-phenyl-1,3,5-triazine (10.0 g, 0.044 mol), 4-Cyanophenylboronic acid (7.8 g, 0.053 mol), K ₂ CO ₃ (18.3 g, 0.133 mol), Pd (PPh ₃ ) ₄ (1.0 g, 0.001 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL 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 7.2 g (yield 55.6%) of <Intermediate 271-1>.

(2) production example 2: Synthesis of compound 271

Intermediate 70-2 (10.0 g, 0.019 mol), Intermediate 271-1 (6.7 g, 0.023 mol), K ₂ CO ₃ (8.0 g, 0.058 mol), Pd(PPh ₃ ) ₄ (0.4 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 7.9 g (yield 63.2%) of <Compound 271>.

LC/MS: m/z=651 [(M) ⁺ ]

Synthesis example 14: Synthesis of compound 273

(One) production example 1: Synthesis of intermediate 273-1

500 mL of DMF was added to 3-Bromocarbazole (10.0 g, 0.041 mol), 2-Fluorobenzonitrile (5.9 g, 0.049 mol), Cs ₂ CO ₃ (8.4 g, 0.061 mol), and the reaction was stirred at 150 ° C. under reflux for 12 hours. . After completion of the reaction, extraction and concentration were performed, followed by column to obtain 9.2 g (yield: 65.2%) of <Intermediate 273-1>.

(2) production example 2: Synthesis of intermediate 273-2

Intermediate 273-1 (10.0 g, 0.029 mol), bis(pinacolato)diboron (8.8 g, 0.035 mol), CH ₃ CO ₂ K (8.5 g, 0.086 mol), Pd(dppf)Cl ₂ (1.0 g, 0.001 mol) ) into 200 mL of dioxane 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 8.5 g (yield 74.9%) of <Intermediate 273-2>.

(3) production example 3: Synthesis of compound 273

Intermediate 273-2 (10.0 g, 0.025 mol), 2-(2-Bromophenyl)-4,6-diphenyl-1,3,5-triazine (11.8 g, 0.030 mol), K ₂ CO ₃ (10.5 g, 0.076) mol), Pd(PPh ₃ ) ₄ (0.6 g, 0.0005 mol), toluene 200 mL, ethanol 50 mL, and H ₂ O 50 mL were added 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 10.1 g (yield: 69.2%) of <Compound 273>.

LC/MS: m/z=575 [(M) ⁺ ]

Synthesis example 15: Synthesis of compound 284

(One) production example 1: Synthesis of compound 284-1

DMF was added to 2-Bromo-1-naphthalenecarboxaldehyde (10.0 g, 0.043 mol), Benzamidine Hydrochloride (13.3 g, 0.085 mol), K ₂ CO ₃ (11.8 g, 0.085 mol), and the reaction was stirred at 120 ° C. for 18 hours. . After completion of the reaction, extraction and concentration were performed to obtain 10.7 g (yield: 57.4%) of <Intermediate 284-1>.

(2) production example 2: Synthesis of intermediate 284-2

Intermediate 273-1 (10.0 g, 0.029 mol), bis(pinacolato)diboron (8.8 g, 0.035 mol), CH ₃ CO ₂ K (8.5 g, 0.086 mol), Pd(dppf)Cl ₂ (1.1 g, 0.001 mol) ) into 200 mL of dioxane 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 73.1%) of <Intermediate 284-2>.

(3) production example 3: Synthesis of compound 284

Intermediate 284-2 (10.0 g, 0.025 mol), Intermediate 284-1 (13.3 g, 0.030 mol), K ₂ CO ₃ (10.5 g, 0.076 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, extraction and concentration were performed, followed by column and recrystallization to obtain 10.8 g (yield 68.1%) of <Compound 284>.

LC/MS: m/z=625 [(M) ⁺ ]

Synthesis example 16: Synthesis of compound 286

(One) production example 1: Synthesis of compound 286

Intermediate 15-2 (10.0 g, 0.023 mol), 2-(4-Bromophenyl)-4,6-diphenyl-1,3,5-triazine (10.5 g, 0.027 mol), K ₂ CO ₃ (9.3 g, 0.067 mol), Pd(PPh ₃ ) ₄ (0.5 g, 0.0004 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, 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 10.2 g (yield 72.5%) of <Compound 286>.

LC/MS: m/z=626 [(M) ⁺ ]

Synthesis example 17: Synthesis of compound 296

(One) production example 1: Synthesis of compound 296

Intermediate 70-2 (10.0 g, 0.019 mol), Intermediate 111-1 (9.3 g, 0.023 mol), K ₂ CO ₃ (8.0 g, 0.058 mol), Pd(PPh ₃ ) ₄ (0.4 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 9.8 g (yield 62.9%) of <Compound 296>.

LC/MS: m/z=762 [(M) ⁺ ]

Synthesis example 18: Synthesis of compound 322

(One) production example 1: Synthesis of compound 322

Intermediate 70-2 (10.0 g, 0.019 mol), 2-Chloro-4,6-bis(3-dibenzofuranyl)-1,3,5-triazine (10.3 g, 0.023 mol), K ₂ CO ₃ (8.0 g, 0.058 mol), Pd(PPh ₃ ) ₄ (0.4 g, 0.0004 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL, 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 57.5%) of <Compound 322>.

LC/MS: m/z=806 [(M) ⁺ ]

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 in size, using an ITO glass substrate to which an ITO transparent electrode is attached, on a glass substrate of 25 mm × 25 mm × 0.7 mm After that, it was 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 80

Using the compound 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 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 (EB1 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 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 [EB1]. In addition, [BH1] was used as a host compound for the light emitting layer, and [BD1] was used as a dopant compound to be co-deposited to a thickness of 20 nm. In addition, the electron transport layer was deposited at 30 nm (Liq doping) using the compound according to the present invention described in Table 1 below, and then LiF was formed to a thickness of 1 nm to form an electron injection layer. Thereafter, Al was formed 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 prepared in the same manner as in the device structure of Example 1 except that the following [ET1] was used instead of the compound according to the present invention for the electron transport layer.

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 structure of the above Example.

device comparative example 3

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

Experimental example 1: element Example 1 to 80 luminescence characteristics

For the organic light emitting devices manufactured according to the above Examples and Comparative Examples, voltage, current and luminous efficiency were measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research), 1000 nit standard The result value of is shown in [Table 1] below.

Example electron transport layer V cd/A CIEx CIEy One Formula 1 3.99 7.65 0.1315 0.1329 2 Formula 2 4.18 7.31 0.1332 0.1353 3 Formula 4 3.78 7.44 0.1324 0.1375 4 Formula 8 4.08 7.68 0.1346 0.1369 5 Formula 12 4.02 7.93 0.1333 0.1387 6 Formula 15 4.17 7.22 0.1308 0.1391 7 Formula 24 4.27 7.44 0.1319 0.1379 8 Formula 28 3.92 7.38 0.1306 0.1392 9 Formula 31 3.68 7.63 0.1334 0.1373 10 Formula 39 3.79 7.47 0.1315 0.1379 11 Formula 47 3.71 7.62 0.1322 0.1385 12 Formula 51 4.27 7.14 0.1332 0.1366 13 Formula 53 4.04 7.15 0.1316 0.1372 14 Formula 55 3.86 7.42 0.1338 0.1336 15 Formula 65 3.81 8.02 0.1327 0.1360 16 Formula 70 4.08 7.23 0.1316 0.1382 17 Formula 73 3.71 7.61 0.1323 0.1369 18 Formula 78 3.76 7.13 0.1302 0.1387 19 Formula 83 4.02 7.32 0.1314 0.1322 20 Formula 84 3.84 7.31 0.132 0.1339 21 Formula 92 4.09 7.64 0.1329 0.1361 22 Formula 96 4.06 7.92 0.1332 0.1355 23 Formula 98 3.93 7.81 0.1306 0.1373 24 Formula 102 3.76 7.34 0.1332 0.1328 25 Formula 108 3.96 7.22 0.1329 0.1358 26 Formula 109 4.04 7.25 0.1328 0.1343 27 Formula 111 4.08 7.22 0.1336 0.1367 28 Formula 112 3.86 7.66 0.1324 0.1389 29 Formula 121 4.17 7.71 0.1323 0.1383 30 Formula 122 3.96 7.32 0.1332 0.1401 31 Formula 128 3.87 7.84 0.1314 0.1329 32 Formula 131 3.99 7.12 0.1313 0.1353 33 Formula 133 4.15 7.65 0.1304 0.1405 34 Formula 148 3.99 7.45 0.133 0.1342 35 Formula 151 3.97 7.61 0.1314 0.1372 36 Formula 159 3.81 7.47 0.135 0.1376 37 Formula 162 3.77 7.22 0.1315 0.1394 38 Formula 170 3.86 7.79 0.133 0.1398 39 Formula 171 4.03 7.73 0.1394 0.1332 40 Formula 177 3.62 7.62 0.1381 0.1372 41 Formula 188 3.93 7.47 0.1364 0.1344 42 Formula 194 3.79 7.13 0.1386 0.1357 43 Formula 203 3.78 7.46 0.1402 0.1308 44 Formula 211 3.87 7.53 0.1344 0.1205 45 Formula 224 3.84 7.85 0.1364 0.1227 46 Formula 227 4.24 7.42 0.1334 0.1371 47 Formula 229 3.86 7.46 0.1334 0.1352 48 Formula 233 3.96 7.34 0.1302 0.1358 49 Formula 246 3.91 7.42 0.1346 0.1338 50 Formula 251 3.98 7.63 0.1335 0.1344 51 Formula 257 3.87 7.47 0.1394 0.1308 52 Formula 269 4.06 7.27 0.1323 0.1338 53 Formula 271 3.92 7.62 0.1335 0.1344 54 Formula 273 3.96 7.85 0.1318 0.1315 55 Formula 284 3.89 7.58 0.1334 0.1339 56 Formula 286 3.86 7.82 0.1354 0.1361 57 Formula 290 3.83 7.34 0.1338 0.1355 58 Formula 291 4.11 7.71 0.1361 0.1373 59 Formula 293 3.67 7.48 0.1350 0.1377 60 Formula 297 3.86 7.22 0.1355 0.1314 61 Formula 300 4.00 7.27 0.1363 0.1385 62 Formula 302 3.90 7.55 0.1334 0.1210 63 Formula 303 3.76 7.21 0.1356 0.1223 64 Formula 306 3.75 7.54 0.1372 0.1174 65 Formula 309 3.84 7.69 0.1334 0.1255 66 Formula 310 4.15 7.74 0.1333 0.1249 67 Formula 311 3.94 7.35 0.1342 0.1267 68 Formula 313 4.13 7.68 0.1314 0.1271 69 Formula 315 3.97 7.48 0.1347 0.1208 70 Formula 318 4.22 7.12 0.1369 0.1344 71 Formula 321 4.15 7.62 0.1355 0.1357 72 Formula 322 3.81 7.37 0.1348 0.1221 73 Formula 325 4.06 7.16 0.1317 0.1377 74 Formula 328 4.01 7.47 0.1344 0.1314 75 Formula 330 3.78 7.19 0.1335 0.1344 76 Formula 331 4.09 7.22 0.1316 0.1357 77 Formula 333 4.20 7.15 0.1379 0.1212 78 Formula 335 4.13 7.65 0.1365 0.1223 79 Formula 336 3.89 7.43 0.1356 0.1204 80 Formula 337 3.96 7.66 0.1345 0.1217 Comparative Example 1 ET 1 4.65 6.45 0.1337 0.1587 Comparative Example 2 ET 2 4.46 6.93 0.1387 0.1457 Comparative Example 3 ET 3 4.37 6.85 0.1354 0.1438

Looking at the results shown in [Table 1], when the compound according to the present invention is applied to the electron transport layer in the organic light emitting device, a compound used as a conventional electron transport material or a compound in contrast to the characteristic structure of the compound according to the present invention It can be seen that the luminescent properties such as luminous efficiency and quantum efficiency are significantly superior to those of the employed devices (Comparative Examples 1 to 3).

[HAT_CN] [α-NPB] [BH1] [BD1] [ET1]

[EB1] [ET2] [ET3]

Claims (7)

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

In the above [Formula I],
L is a single bond, or is selected from a substituted or unsubstituted C6-C30 arylene group and a substituted or unsubstituted C3-C30 heteroarylene group,
n is an integer of 0 to 3, and when n is 2 or more, the plurality of Ls are the same or different from each other,
X _{One To} X _{3 Are} the same as or different from each other and each independently represent CH or N, wherein at least two or more of _{X One To} X _{3 are N,}
R ₁ is a cyano group, a halogen group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C 3 to C 20 cycloalkyl group, substituted or unsubstituted A substituted or unsubstituted C 1 to C 20 alkoxy group, a substituted or unsubstituted C 1 to C 20 halogenated alkyl group, a substituted or unsubstituted C 1 to C 20 halogenated alkoxy group, a substituted or unsubstituted C 6 to C 30 aryl It is selected from a group and a substituted or unsubstituted C 3 to C 30 heteroaryl group,
Ar ₁ to Ar ₂ are the same as or different from each other, and are each independently 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. The method of claim 1,
In the definitions of L, Ar ₁ to Ar ₂ and R ₁ , 'substituted or unsubstituted' means that L, Ar ₁ to Ar ₂ and R ₁ are deuterium, a halogen group, a cyano group, a nitro group, and a hydroxyl group, respectively. , silyl group, alkyl group, halogenated alkyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, halogenated alkoxy group, alkenyl group, substituted with one or two or more substituents selected from the group consisting of an aryl group and a heteroaryl group, or among the substituents An organic light emitting compound, characterized in that it is substituted with a substituent to which two or more substituents are connected, or does not have any substituents. The method of claim 1,
The [Formula I] is an organic light emitting compound, characterized in that any one selected from the following compounds [1] to [337]:

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 at least one organic light emitting compound implemented by [Formula I] according to claim 1. 5. The method of claim 4,
The organic layer includes at least one of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer,
At least one of the layers comprises an organic light emitting compound represented by the [Formula I]. 6. The method of claim 5,
The organic light emitting device, characterized in that the electron transport layer comprises an organic light emitting compound represented by the [Formula I]. 7. The method of claim 6,
The electron transport layer includes, in addition to the organic light emitting compound represented by the [Formula I], further mixing one or more electron transport compounds,
The electron transport layer consists of a plurality of electron transport layers, and any one of the electron transport layer is an organic light emitting device, characterized in that it comprises an organic light emitting compound represented by the [Formula I].