KR102438615B1 - An organic light emitting compound and an organic light emitting diode comprising the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by the following [Formula I], and an organic light emitting device employing the organic light emitting compound according to the present invention, in particular, the organic light emitting compound according to the present invention as an electron injection and electron transport material Compared to the conventional organic light emitting device, the organic light emitting device has improved low driving voltage and long lifespan, and thus can be usefully used in various display and lighting industries.
[Formula Ⅰ]

Description

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

The present invention relates to an organic light emitting compound, and more particularly, to an organic light emitting compound having a specific structure used as an electron transport layer, and to an organic light emitting compound capable of implementing long lifespan, low voltage and high efficiency light emitting characteristics, and an organic light emitting device including the same it's about

An organic light emitting diode (OLED) is a display using a self-emission phenomenon, has a large viewing angle, can be lightweight and compact compared to a liquid crystal display, and has advantages such as a fast response speed. ) is expected to be applied to displays or lighting.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material, and an organic light emitting device using the organic light emitting phenomenon has a structure including an anode and a cathode and an organic material layer therebetween.

Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.

In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and these excitons are It lights up when it falls back to the ground state. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

The material used as the organic layer in the organic light emitting device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc., depending on the function. Alternatively, a hole blocking layer or the like may be added.

Among them, as a prior art related to a material for an electron transport layer, a pyridoindole in a substituted anthracene ring structure to prepare an organic compound having excellent electron transport ability and hole blocking ability, excellent luminous efficiency, and high stability in a thin film state Anthracene derivatives having a pyridine naphthyl group and the like are known, which are organic compounds bound with derivatives, and the like, which have excellent characteristics of external quantum efficiency and driving voltage characteristics.

However, although various kinds of methods for manufacturing an organic light emitting device having more efficient light emitting characteristics have been tried, there is a continuous demand for the development of an organic light emitting device having a long lifespan, low voltage and high efficiency.

Therefore, the problem to be solved by the present invention is to solve the above problems, and by introducing a material having a specific structure into the electron transport layer, an organic light emitting compound capable of implementing an organic light emitting device having long lifespan, low voltage and high efficiency characteristics To provide an organic light emitting compound will be.

In addition, an object of the present invention is to provide an organic light emitting device having characteristics of low voltage driving, high efficiency and long life by employing the organic light emitting compound as a light emitting material.

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 specific substituents of the [Formula I] will be described later.

An organic light emitting device employing the organic light emitting compound according to the present invention, in particular, an organic light emitting device employing the organic light emitting compound according to the present invention as an electron injection and electron transport material has a lower driving voltage, longer lifespan, and It has excellent light emitting characteristics such as high efficiency and can be usefully used in various display and lighting industries.

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

The present invention relates to an organic light emitting compound represented by the following [Formula I], which is employed as an electron injection or electron transport compound in an organic material layer of organic light emitting irradiation to further improve the efficiency, lifespan characteristics and driving voltage characteristics of the device. characterized.

[Formula Ⅰ]

In the above [Formula I],

L is a linking group, a single bond or a substituted or unsubstituted C 1 to C 30 alkylene group, a substituted or unsubstituted C 2 to C 30 alkenylene group, a substituted or unsubstituted C 2 to C 30 alkynylene group, substituted Or an unsubstituted cycloalkylene group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted C2 to 30 carbon atoms It may be any one selected from the hetero arylene group of.

According to an embodiment of the present invention, L is a single bond, or may be any one selected from the following [Structural Formula 1] to [Structural Formula 9], and the following [Structural Formula 1] to [Structural Formula 9], the carbon of the aromatic ring The site is bonded to hydrogen or deuterium.

[Structural formula 1] [Structural formula 2] [Structural formula 3] [Structural formula 4]

[Structural formula 5] [Structural formula 6] [Structural formula 7]

[Structural formula 8] [Structural formula 9]

n is an integer of 1 to 3, and when L is plural, each may be the same or different from each other.

HAr ₂ may be any one selected from the following [Structural Formula A] to [Structural Formula E].

[Formula A] [Formula B]

[Formula C] [Formula D]

[Structural Formula E]

In the [Structural Formula A] to [Structural Formula E],

X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, X5 is CR15 or N, X6 is CR16 or N, X7 is CR17 or N, X8 is CR18 or N, X9 is CR19 or N, and X10 is CR20 or N.

At least two of X1 to X4 are selected from CR11 to CR14, at least three of X5 to X10 are selected from CR15 to CR20, and one of X1 to X10 is a carbon atom connected to L.

R1, R2 and R11 to R20 are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted an alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 of an arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted and a heteroaryl group having 2 to 50 carbon atoms having O, N or S as a heteroatom, a substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 24 carbon atoms, an amino group, thi It may be any one selected from an ol group, a cyano group, a hydroxyl group, a nitro group, and a halogen group.

A substituent not bonded to L among R11 to R20 may be hydrogen or deuterium, and only one of X1 to X10 may be a nitrogen atom or not all of them may be a nitrogen atom.

In more detail with respect to the [Structural Formula A] to [Structural Formula E] corresponding to one of the characteristic structures in [Formula I] according to the present invention, '6 membered ring aromatic ring comprising X1 to X4 - connected to R1 and R2 5-membered ring containing carbon atoms - X5 and X10 or, X5 and X6 or 6-membered aromatic carbocyclic ring containing X9 and X10 - 5-membered ring containing oxygen atoms - X6 to X9 or, X7 to X10 or, X5 to X8 A 6-membered aromatic ring comprising characterized.

HAr ₁ may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, preferably a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. have.

According to a preferred embodiment of the present invention, the HAr ₁ may be any one selected from the following [Structural Formula E1] to [Structural Formula E33].

In the [Structural Formula E1] to [Structural Formula E33],

Z ₁ to Z ₈ are the same as or different from each other, and are each independently the same as the definitions of R1, R2 and R11 to R20,

The Z ₁ to Z ₈ and substituents thereof may form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with substituents adjacent to each other.

In addition, 'substitution' in 'substituted or unsubstituted' means deuterium, cyano group, halogen group, hydroxy group, nitro group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C2-C24 Alkenyl group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 arylalkyl group, C2-C24 heteroaryl group or C2-C24 hetero Arylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 heteroarylamino group, C1-C24 alkylsilyl group, C6-C24 arylamino group It means substituted with one or more substituents selected from the group consisting of an arylsilyl group and an aryloxy group having 6 to 24 carbon atoms.

On the other hand, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 30 carbon atoms" in the present invention, The range of carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 30 carbon atoms means the total number of carbon atoms constituting the alkyl part or the aryl part when viewed as unsubstituted without considering the substituted part of the substituent. will be. For example, a phenyl group substituted with a butyl group at the para position should be regarded as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

Meanwhile, specific examples of the alkyl group used in the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, a heptyl group. , octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, and the like, and at least one hydrogen atom of the alkyl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (referred to as "alkylsilyl group" in this case), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), where R, R' and R" are each Independently an alkyl group having 1 to 24 carbon atoms (referred to as “alkylamino group” in this case), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-C24 alkyl group, C1-C24 alkyl group Halogenated alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C5-C24 aryl group, C6-C24 arylalkyl group, C3-C24 hetero It may be substituted with an aryl group or a heteroarylalkyl group having 3 to 24 carbon atoms.

Specific examples of the alkoxy group used in the present invention include a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an iso-amyloxy group, a hexyloxy group, and the like. , may be substituted with the same substituents as in the case of the alkyl group.

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

The aryloxy group used in the present invention refers to an -O- aryl radical, wherein the aryl group is as defined above, and specific examples thereof include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyloxy, indenyloxy and the like, and one or more hydrogen atoms included in the aryloxy group may be further substituted.

Specific examples of the silyl group used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl and the like.

The aryl group used in the present invention is an organic radical derived from an aromatic hydrocarbon by removal of one hydrogen, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members, and the aryl group When there is a substituent, it may be fused with a neighboring substituent to further form a ring.

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group and aromatic groups such as , pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

In addition, the aryl group may also be further substituted with one or more substituents, and more specifically, at least one hydrogen atom of the aryl group is a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R"), R' and R" are each independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C1-C24 alkenyl group, C1-C24 alkynyl group, C1-C24 hetero It may be substituted with an alkyl group, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, or the like.

In addition, the heteroaryl group used in the present invention contains 1, 2 or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, Te, and the remaining ring atoms are carbon atoms of 2 to 24 carbon atoms. An aromatic system, wherein the rings may be fused to form a ring. And one or more hydrogen atoms in the heteroaryl group may be substituted with the same substituents as in the case of the aryl group.

In addition, in the present invention, the aromatic heterocycle means that at least one of the aromatic carbons in the aromatic hydrocarbon ring is substituted with at least one hetero atom selected from N, O, P, Si, S, Ge, Se, and Te.

The organic light emitting compound represented by [Formula I] according to the present invention may be any one selected from the following [Compound 1] to [Compound 564], whereby the scope of [Formula I] is not limited thereto.

In addition, the present invention relates to an organic light emitting device comprising an organic light emitting compound according to the above [Formula I], comprising an organic layer between the opposed first and second electrodes, wherein the organic layer is a light emitting layer, an electron transport layer, a hole It may include some or all selected from a transport layer, an electron injection layer, a hole injection layer, a hole blocking layer, and an electron blocking layer, and the organic light emitting compound according to the present invention is characterized in that it is included in the electron transport layer or the electron injection layer. do.

In this case, in the present invention, "including an organic compound" means "the organic layer may include one type of organic compound according to [Formula I] or two or more different compounds belonging to the scope of [Formula I]" can be interpreted.

Hereinafter, the organic light emitting device according to the present invention will be described in more detail.

The organic light emitting device according to the present invention includes an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode, and may further include a hole injection layer and an electron injection layer if necessary, and in addition to that, an intermediate layer of one or two layers It is also possible to further form, a hole blocking layer or an electron blocking layer may be further formed, and may further include an organic layer having various functions according to the characteristics of the device.

Looking at the organic light emitting device and the method for manufacturing the same according to the present invention, first, a material for an anode electrode is coated on an upper substrate to form an anode. Here, as the substrate, a substrate used in a conventional organic light emitting device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handling and water resistance is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used as a material for the anode electrode.

A hole injection layer is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on the anode electrode. Next, a hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection layer.

The hole injection layer material may be used without particular limitation as long as it is commonly used in the art, and as a specific example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] can be used.

In addition, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1 -biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD), etc. can be used.

Subsequently, a thin film may be formed by laminating a light emitting layer on the hole transport layer and selectively depositing a hole blocking layer on the light emitting layer by a vacuum deposition method or a spin coating method. The hole blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifetime and efficiency of the device are reduced when holes are introduced into the cathode through the organic light emitting layer. . In this case, the hole blocking material used is not particularly limited, but has an electron transport ability and has an ionization potential higher than that of a light emitting compound, and typically BAlq, BCP, TPBI, or the like may be used.

After depositing an electron transport layer on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer is formed, and a cathode forming metal is vacuum thermally deposited on the electron injection layer to form a cathode electrode. The small is complete. Here, as the metal for forming the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

The electron transport layer material serves to stably transport electrons injected from the electron injection electrode (Cathode), and the organic light emitting compound of [Formula I] according to the present invention is used.

In addition, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process, wherein the deposition method means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is used as a material for forming each layer It refers to a method of mixing a material to be used with a solvent and forming a thin film through a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, and the like.

In addition, the organic light emitting diode according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, and a monochromatic or white flexible lighting device.

Hereinafter, the present invention will be described in more detail through a method for synthesizing a specific dye compound according to the present invention, examples, and comparative experiments. However, the examples are only intended to illustrate the present invention, and are not intended to limit the scope of the present invention.

Synthesis example 1. [Compound 1] of synthesis

Synthesis example 1-1. Synthesis of [Intermediate 1-a]

[1-a]

In a round-bottom flask, 25 g (118 mmol) of dibenzofuran-1-boronic acid, 40.5 g (118 mmol) of methyl-5-bromo-2-iodobenzoate, 2.7 g (2.3 g) of tetrakistriphenylphosphine palladium mmol), potassium carbonate 33 g (237 mmol), toluene 200 mL, 1,4-dioxane 200 mL, and water 100 mL were added under nitrogen and refluxed for 12 hours. After completion of the reaction, the reaction product was separated into layers, and the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain 33.5 g of [Intermediate 1-a]. (Yield 74%)

Synthesis example 1-2. Synthesis of [Intermediate 1-b]

[1-b]

Put 33.5 g (110 mmol) of [Intermediate 1-a] in a round-bottom flask containing 150 mL of tetrahydrofuran, lower the temperature to -10 °C, and then slowly add 85 mL (254 mmol) of 3 M methylmagnesium bromide dropwise. After raising the temperature to 40 ℃, stirred for 4 hours. After lowering the temperature to -10 °C, slowly add 70 mL of 2 N hydrochloric acid dropwise, and then add 70 mL of ammonium chloride aqueous solution, and then raise the temperature to room temperature. After completion of the reaction, the reaction product was washed with water, concentrated under reduced pressure, and separated by column chromatography to obtain 27 g of [Intermediate 1-b]. (yield 80%)

Synthesis example 1-3. Synthesis of [Intermediate 1-c]

[1-c]

27 g (89.2 mmol) of [Intermediate 1-b] and 70 mL of phosphoric acid were added to a round-bottom flask under a nitrogen atmosphere, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was extracted, concentrated, and separated by column chromatography to obtain 17.6 g of [Intermediate 1-c]. (yield 70%)

Synthesis example 1-4. Synthesis of [Intermediate 1-d]

[1-d]

Put 17.6 g (48.4 mmol) of [Intermediate 1-c] in a round-bottom flask, add 200 mL of tetrahydrofuran under a nitrogen atmosphere, lower the temperature to -78°C, and then slowly add 36.3 mL (58.1 mmol) of 1.6 M butyllithium dropwise. do. After 1 hour, 7.0 mL (62.9 mmol) of trimethylborate was slowly added while maintaining the low temperature, and the temperature was raised to room temperature and stirred. After completion of the reaction, the organic layer was concentrated under reduced pressure and recrystallized from hexane to obtain 13 g of [Intermediate 1-d] (yield 82%).

Synthesis example 1-5. [compound 1] of synthesis

[One]

[Intermediate 1-d] 5 g (15.2 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine 6.5 g (16.7 mmol), tetrakistriphenylphosphinepalladium in a round bottom flask 0.3 g (0.3 mmol), potassium carbonate 4.2 g (30.4 mmol), toluene 25 mL, 1,4-dioxane 25 mL, and water 15 mL were added under nitrogen and refluxed for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 6.8 g of [Compound 1]. (yield 76%)

MS (MALDI-TOF): m/z 515.20 [M] ⁺

Synthesis example 2. [Compound 5] of synthesis

Synthesis example 2-1. Synthesis of [Intermediate 2-a]

[2-a]

Using 2,4-dichloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, [ [Intermediate 2-a] was obtained by synthesizing in the same manner except that 1-naphthaleneboronic acid was used instead of Intermediate 1-d]. (Yield 42%)

Synthesis example 2-2. [compound 5] of synthesis

[5]

[Compound 5] was obtained by synthesizing in the same manner except that [Intermediate 2-a] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 . (yield 72%)

MS (MALDI-TOF): m/z 565.22 [M] ⁺

Synthesis example 3. [Compound 71] of synthesis

Synthesis example 3-1. Synthesis of [Intermediate 3-a]

[3-a]

In a round-bottom flask, 50 g (183 mmol) of 2-bromo-9,9-dimethylfluorene, 59.3 g (1098 mmol) of sodium methoxide solution, 10.4 g (54.9 mmol) of copper iodide, and 200 mL of methanol were placed under nitrogen. added and refluxed for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 33.2 g of [Intermediate 3-a]. (Yield 81%)

Synthesis example 3-2. Synthesis of [Intermediate 3-b]

[3-b]

[Intermediate 3-a] 30 g (133 mmol), N-bromosuccinimide 23.8 g (133 mmol), and dimethylformamide 600 mL were added to a round-bottom flask under nitrogen and stirred at 50 °C for 12 hours. . After completion of the reaction, the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 28 g of [Intermediate 3-b]. (yield 70%)

Synthesis example 3-3. Synthesis of [Intermediate 3-c]

[3-c]

[Intermediate 3-c] was obtained by synthesizing in the same manner except that [Intermediate 3-b] was used instead of [Intermediate 1-c] used in Synthesis Example 1-4. (yield 77%)

Synthesis example 3-4. Synthesis of [Intermediate 3-d]

[3-d]

Using 1-bromo-3-chloro-2-fluorobenzene instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, [Intermediate 1-d ] was synthesized in the same manner except that [Intermediate 3-c] was used instead of [Intermediate 3-d] to obtain [Intermediate 3-d]. (Yield 52%)

Synthesis example 3-5. Synthesis of [Intermediate 3-e]

[3-e]

In a round-bottom flask, 30 g (85 mmol) of [intermediate 3-d] and 300 mL of dichloromethane were added under nitrogen, the temperature was lowered to 0 ° C, and 63.9 g (255 mmol) of borontribromide was diluted in 150 mL of dichloromethane. and add it slowly After raising the temperature to room temperature, the mixture was stirred for 6 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, and separated by column chromatography to obtain 21.3 g of [Intermediate 3-e]. (Yield 74%)

Synthesis example 3-6. Synthesis of [Intermediate 3-f]

[3-f]

20 g (59 mmol) of [Intermediate 3-e], 13 g (94.5 mmol) of potassium carbonate, and 200 mL of 1-methyl-2-pyrrolidinone were added to a round-bottom flask under nitrogen and stirred at 150° C. for 12 hours. did. After completion of the reaction, the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 13.5 g of [Intermediate 3-f]. (yield 72%)

Synthesis example 3-7. Synthesis of [Intermediate 3-g]

[3-g]

[Intermediate 3-f] 13 g (40.8 mmol), bis (pinacolato) diborane 12.4 g (48.9 mmol), tris (dibenzylideneacetone) palladium 2 g (2.4 mmol), potassium acetate 11.6 in a round bottom flask g (122 mmol), tricyclohexylphosphine 2.7 g (9.8 mmol), and 150 mL of N-dimethylformamide were added under nitrogen and refluxed. After completion of the reaction, the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 10.8 g of [Intermediate 3-g]. (Yield 65%)

Synthesis example 3-8. [compound 71] of synthesis

[71]

[Compound 71] was obtained by synthesizing in the same manner except that [Intermediate 3-g] was used instead of [Intermediate 1-d] used in Synthesis Example 1-5. (yield 69%)

MS (MALDI-TOF): m/z 515.20 [M] ⁺

Synthesis example 4. [Compound 72] synthesis

Synthesis example 4-1. [compound 72] synthesis

[72]

2-(3-bromophenyl)-4,6-diphenyl-1,3,5- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 Triazine was used and [Compound 72] was obtained by synthesizing in the same manner except that [Intermediate 3-g] was used instead of [Intermediate 1-d]. (Yield 46%)

MS (MALDI-TOF): m/z 591.23 [M] ⁺

Synthesis example 5. [Compound 164] of synthesis

Synthesis example 5-1. Synthesis of [Intermediate 5-a]

[5-a]

Using 3-bromodibenzofuran instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, and using phenylboronic acid instead of [Intermediate 1-d] Except for the synthesis, [Intermediate 5-a] was obtained. (yield 76%)

Synthesis example 5-2. Synthesis of [Intermediate 5-b]

[5-b]

In a round-bottom flask, 50 g (204 mmol) of [Intermediate 5-a] and 500 mL of tetrahydrofuran were added under nitrogen, and the temperature was lowered to -78 ° C. Then, 128 mL (204 mmol) of 1.6 M-butyllithium was slowly added dropwise. Stirred for 1 hour. Acetone 14.3 g (245 mmol) was slowly added dropwise, followed by stirring at room temperature for 6 hours. After completion of the reaction, 50 mL of an aqueous ammonium chloride solution was added, the layers were separated, the organic layer was concentrated under reduced pressure, and column chromatography was used to obtain 38.3 g of [Intermediate 5-b]. (Yield 62%)

Synthesis example 5-3. Synthesis of [Intermediate 5-c]

[5-c]

[Intermediate 5-c] was obtained by synthesizing in the same manner except that [Intermediate 5-b] was used instead of [Intermediate 1-b] used in Synthesis Example 1-3. (yield 69%)

Synthesis example 5-4. Synthesis of [Intermediate 5-d]

[5-d]

[Intermediate 5-c] 14.5 g (50.9 mmol) and 150 mL of dichloromethane were added to a 1 L reactor and stirred. At room temperature, 8.9 g (56 mmol) of bromine was slowly added dropwise, followed by stirring for 5 hours. After completion of the reaction, the precipitate was collected using methanol and filtered to obtain 9.4 g of [Intermediate 5-d]. (Yield 51%)

Synthesis example 5-5. Synthesis of [Intermediate 5-e]

[5-e]

[Intermediate 5-e] was obtained by synthesizing in the same manner except that [Intermediate 5-d] was used instead of [Intermediate 1-c] used in Synthesis Example 1-4. (Yield 65%)

Synthesis example 5-6. [compound 164] of synthesis

[164]

[Compound 164] was obtained by synthesizing in the same manner except that [Intermediate 5-e] was used instead of [Intermediate 1-d] used in Synthesis Example 1-5. (Yield 73%)

MS (MALDI-TOF): m/z 515.20 [M] ⁺

Synthesis example 6. [Compound 167] of synthesis

Synthesis example 6-1. [compound 167] of synthesis

[167]

2-(4-bromophenyl)-4,6-diphenyl-1,3,5- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 [Compound 167] was obtained by synthesis in the same manner except that triazine was used and [Intermediate 5-e] was used instead of [Intermediate 1-d]. (Yield 48%)

MS (MALDI-TOF): m/z 591.23 [M] ⁺

Synthesis example 7. [Compound 197] of synthesis

Synthesis example 7-1. Synthesis of [Intermediate 7-a]

[7-a]

Use dibenzofuran-3-boronic acid instead of dibenzofuran-1-boronic acid used in Synthesis Example 1-1, and methyl-5-bromo-1 instead of methyl-5-bromo-2-iodobenzoate - It was synthesized in the same manner as in Synthesis Examples 1-1 to 1-4 using iodobenzoate to obtain [Intermediate 7-a]. (Yield 66%)

Synthesis example 7-2. [compound 197] of synthesis

[197]

[Compound 197] was obtained by synthesizing in the same manner except that [Intermediate 7-a] was used instead of [Intermediate 1-d] used in Synthesis Example 1-5. (Yield 63%)

MS (MALDI-TOF): m/z 515.20 [M] ⁺

Synthesis example 8. [Compound 200] synthesis

Synthesis example 8-1. [compound 200] synthesis

[200]

2-(4-bromophenyl)-4,6-diphenyl-1,3,5- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 Triazine was used and [Compound 200] was obtained by synthesizing in the same manner except that [Intermediate 7-a] was used instead of [Intermediate 1-d]. (Yield 68%)

MS (MALDI-TOF): m/z 591.23 [M] ⁺

Synthesis example 9. [Compound 233] of synthesis

Synthesis example 9-1. Synthesis of [Intermediate 9-a]

[9-a]

In a round-bottom flask, 50 g (202 mmol) of 3-bromodibenzofuran, 54.6 g (1214 mmol) of sodium methoxide solution, 11.5 g (60.7 mmol) of copper iodide, and 200 mL of methanol were added under nitrogen and refluxed for 12 hours. did it After completion of the reaction, the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 36 g of [Intermediate 9-a]. (yield 90%)

Synthesis example 9-2. Synthesis of [Intermediate 9-b]

[9-b]

36 g (181 mmol) of [Intermediate 9-a], 32.3 g (181 mmol) of N-bromosuccinimide, and 700 mL of dimethylformamide were added to a round-bottom flask under nitrogen, followed by stirring at 50 °C for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 35 g of [Intermediate 9-b]. (yield 70%)

Synthesis example 9-3. Synthesis of [Intermediate 9-c]

[9-c]

[Intermediate 9-c] was obtained by synthesizing in the same manner except that [Intermediate 9-b] was used instead of [Intermediate 1-c] used in Synthesis Example 1-4. (Yield 71%)

Synthesis example 9-4. Synthesis of [Intermediate 9-d]

[9-d]

Using methyl-2-bromobenzoate instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, [Intermediate 1-d] instead of [Intermediate 9- c] was synthesized in the same manner except that [Intermediate 9-d] was obtained. (Yield 64%)

Synthesis example 9-5. Synthesis of [Intermediate 9-e]

[9-e]

[Intermediate 9-e] was obtained by synthesizing in the same manner except that [Intermediate 9-d] was used instead of [Intermediate 1-a] used in Synthesis Example 1-2. (yield 77%)

Synthesis example 9-6. Synthesis of [Intermediate 9-f]

[9-f]

[Intermediate 9-f] was obtained by synthesizing in the same manner except that [Intermediate 9-e] was used instead of [Intermediate 1-b] used in Synthesis Example 1-3. (Yield 67%)

Synthesis example 9-7. Synthesis of [Intermediate 9-g]

[9-g]

Add 30 g (95.4 mmol) of [Intermediate 9-f] and 200 mL of dichloromethane to a round-bottom flask under a nitrogen atmosphere and lower the temperature to 0 °C. 120 g (143 mmol) of boron tribromide was diluted in 300 mL of dichloromethane and slowly added dropwise, followed by stirring at room temperature for 3 hours. After completion of the reaction, the reaction solution was added to 1 L of distilled water, the organic layer was concentrated under reduced pressure, and column chromatography was performed to obtain 19.2 g of [Intermediate 9-g]. (Yield 67%)

Synthesis example 9-8. Synthesis of [Intermediate 9-h]

[9-h]

Put 10 g (33.2 mmol) of [Intermediate 9-g] in a round-bottom flask under nitrogen and lower the temperature to 0 °C. 3.2 mL (39.9 mmol) of pyridine and 7.3 mL (43.2 mmol) of trifluoromethanesulfonic anhydride were slowly added dropwise, followed by stirring at room temperature for 2 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, and separated by column chromatography to obtain 12.2 g of [Intermediate 9-h]. (yield 85%)

Synthesis example 9-9. Synthesis of [Intermediate 9-i]

[9-i]

In a round-bottom flask, 8.5 g (26.7 mmol) of [Intermediate 9-h], 8.8 g (34.7 mmol) of bis(pinacolato)diborane, 1 g (1.3 mmol) of (diphenylphosphinoferrocene)palladium dichloride, acetic acid Potassium 7.6 g (80 mmol) and toluene 90 mL were added under nitrogen and refluxed for 12 hours. After completion of the reaction, the organic layer was concentrated under reduced pressure, and then separated by column chromatography to obtain 8 g of [Intermediate 9-i]. (yield 75%)

Synthesis example 9-10. [compound 233] of synthesis

[233]

[Compound 233] was obtained by synthesizing in the same manner except that [Intermediate 9-i] was used instead of [Intermediate 1-d] used in Synthesis Example 1-5. (yield 78%)

MS (MALDI-TOF): m/z 515.20 [M] ⁺

Synthesis example 10. [Compound 234] of synthesis

Synthesis example 10-1. [compound 234] of synthesis

[234]

2-(3-bromophenyl)-4,6-diphenyl-1,3,5- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 [Compound 234] was obtained by synthesis in the same manner except that triazine was used and [Intermediate 9-i] was used instead of [Intermediate 1-d]. (Yield 52%)

MS (MALDI-TOF): m/z 591.23 [M] ⁺

Synthesis example 11. [Compound 293] of synthesis

Synthesis example 11-1. Synthesis of [Intermediate 11-a]

[11-a]

In a 500 mL reactor, 37 g (156 mmol) of (3-amino-benzofuran-2-yl)-phenyl-methanone, 16.9 g (281 mmol) of urea, and 185 mL of acetic acid are added, and the mixture is stirred under reflux for 12 hours. After completion of the reaction, an excess of water is added to the reactant to precipitate, followed by filtration. After hot slurry with methanol, filtered, hot slurry with toluene, filtered and dried to obtain 24 g of [Intermediate 11-a]. (yield 59%)

Synthesis example 11-2. Synthesis of [Intermediate 11-b]

[11-b]

In a 500 mL reactor, 15 g (44 mmol) of [Intermediate 11-a] and 150 mL of phosphorus oxychloride are added, and the mixture is stirred under reflux for 3 hours. After completion of the reaction, the reactant is slowly added to excess water at 0° C. to precipitate, followed by filtration. After separation by column chromatography, 21 g of [Intermediate 11-b] was obtained. (Yield 81%)

Synthesis example 11-3. [compound 293] of synthesis

[293]

[Intermediate 11-b] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, and [Intermediate 5-e] was used instead of [Intermediate 1-d] [Compound 293] was obtained by synthesizing in the same manner except that (Yield 57%)

MS (MALDI-TOF): m/z 528.18 [M] ⁺

Synthesis example 12. [Compound 313] of synthesis

Synthesis example 12-1. Synthesis of [Intermediate 12-a]

[12-a]

In a 1L reactor, 27.4 g (232 mmol) of 2-aminobenzonitrile and 300 mL of tetrahydrofuran were added and stirred. After cooling to 0 °C, 88.2 mL (487 mmol) of 3M-phenylmagnesium bromide was added dropwise, followed by refluxing for 3 hours. After cooling to 0 °C, 44.3 g (732 mmol) of ethylchloroformate was dissolved in 200 mL of tetrahydrofuran and added dropwise, followed by reflux for 2 hours. After cooling to 0 °C, a saturated aqueous ammonium chloride solution was added, and the organic layer was extracted. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 40 g of [Intermediate 12-a] (yield 78%).

Synthesis example 12-2. Synthesis of [Intermediate 12-b]

[12-b]

In a 1L reactor, 40 g (181 mmol) of [Intermediate 12-a] and 400 mL of phosphorus oxychloride were added and refluxed for 5 hours. After cooling to 0 °C, distilled water was added dropwise. After filtration of the reaction solution, it was separated by column chromatography to obtain 29.5 g (yield 68%) of [Intermediate 12-b].

Synthesis example 12-3. [compound 313] of synthesis

[313]

[Intermediate 12-b] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, and [Intermediate 3-g] was used instead of [Intermediate 1-d] [Compound 313] was obtained by synthesizing in the same manner except that . (Yield 54%)

MS (MALDI-TOF): m/z 488.19 [M] ⁺

Synthesis example 13. [Compound 329] of synthesis

Synthesis example 13-1. Synthesis of [Intermediate 13-a]

[13-a]

In a 2 L reactor, 90 g (676 mmol) of 2-hydroxyphenylacetonitrile, 68.8 g (338 mmol) of 4-dimethylaminopyridine, 137 g (1352 mmol) of triethylamine, and 900 mL of methylene chloride were placed at 0 °C. 82.4 g (676 mmol) of benzoyl chloride is added dropwise. After dropwise addition, the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the mixture was concentrated and separated by column chromatography to obtain 40 g of [Intermediate 13-a]. (Yield 61%)

Synthesis example 13-2. Synthesis of [Intermediate 13-b]

[13-b]

[Intermediate 13-a] 40 g (169 mmol), tricyclohexylphosphine 9.5 g (34 mmol), zinc 1.9 g (17 mmol), palladium acetate 3.8 g (17 mmol), dimethylformamide 400 in a 1 L reactor mL, and stirred under reflux for 12 hours under nitrogen. After completion of the reaction, the reactant was added dropwise to excess water at room temperature to form brown crystals, filtered and separated by column chromatography to obtain 20 g of [Intermediate 13-b]. (Yield 52%)

Synthesis example 13-3. Synthesis of [Intermediate 13-c]

[13-c]

10 g of [Intermediate 13-c] synthesized in the same manner except that [Intermediate 13-b] was used instead of (3-amino-benzofuran-2-yl)-phenyl-methanone used in Synthesis Example 11-1 got (Yield 62%)

Synthesis example 13-4. Synthesis of [Intermediate 13-d]

[13-d]

[Intermediate 13-d] was obtained by synthesizing in the same manner except that [Intermediate 13-c] was used instead of [Intermediate 11-a] used in Synthesis Example 11-2. (yield 77%)

Synthesis example 13-6. [compound 329] of synthesis

[329]

[Compound 329] was obtained by synthesizing in the same manner except that [Intermediate 13-d] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5. . (Yield 54%)

MS (MALDI-TOF): m/z 528.18 [M] ⁺

Synthesis example 14. [Compound 341] of synthesis

Synthesis example 14-1. [compound 341] of synthesis

[341]

[Intermediate 12-b] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, and [Intermediate 9-i] was used instead of [Intermediate 1-d] Except for using , it was synthesized in the same manner to obtain [Compound 341]. (yield 58%)

MS (MALDI-TOF): m/z 488.19 [M] ⁺

Synthesis example 15. [Compound 370] of synthesis

Synthesis example 15-1. Synthesis of [Intermediate 15-a]

[15-a]

In a 2 L round-bottom flask under nitrogen atmosphere, ethyl cyano acetate (139.8 g, 1.236 mol), potassium cyanide (29.5 g, 0.453 mol), potassium hydroxide (46.2 g, 0.824 mol), 920 mL of dimethylformamide After dissolving, the mixture was stirred at 10 °C for 20 minutes. Thereafter, 1-nitronaphthalene (92 g, 531 mol) was added to the reaction mixture and stirred at 60° C. for 4 hours. After completion of the reaction, the solvent is concentrated, 600 mL of a 10% aqueous sodium hydroxide solution is added, and the mixture is stirred under reflux for 1 hour. The solid was filtered and separated by column chromatography to obtain [Intermediate 15-a] (50 g, 56%).

Synthesis example 15-2. Synthesis of [Intermediate 15-b]

[15-b]

After filling a 1 L round-bottom flask with nitrogen [Intermediate 15-a] (20.0 g, 169 mmol), 200 mL of tetrahydrofuran was added, and 3 M-phenylmagnesium bromide (113 mL, 623 mmol) was slowly added dropwise at 0 °C. After that, the mixture was stirred under reflux for 3 hours. When the starting material disappears, the temperature is lowered again, and 3-bromobenzoyl chloride (44.58 g, 0.203 mmol) is dissolved in 200 mL of tetrahydrofuran, slowly added dropwise, and stirred under reflux for 2 hours. After completion of the reaction, an aqueous solution of ammonium chloride was added to stop the reaction, the mixture was extracted with ethyl acetate and water, and the organic layer was concentrated under reduced pressure and separated by column chromatography to obtain [Intermediate 15-b] (37 g, 30%).

Synthesis example 15-3. [compound 370] of synthesis

[370]

[Intermediate 15-b] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, and [Intermediate 7-a] was used instead of [Intermediate 1-d] [Compound 370] was obtained by synthesizing in the same manner except that . (Yield 57%)

MS (MALDI-TOF): m/z 614.24 [M] ⁺

Synthesis example 16. [Compound 375] synthesis

Synthesis example 16-1. Synthesis of [Intermediate 16-a]

[16-a]

Using 2,4-dichloro-6-phenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, [ [Intermediate 16-a] was obtained by synthesizing in the same manner except that benzofuran-1-boronic acid was used instead of Intermediate 1-d]. (Yield 42%)

Synthesis example 16-2. Synthesis of [Intermediate 16-b]

[16-b]

[Intermediate 16-b] was obtained by synthesizing in the same manner as in Synthesis Examples 1-2 to 1-4 using 3M-ethylmagnesium bromide instead of 3M-methylmagnesium bromide used in Synthesis Example 1-2. (Yield 55%)

Synthesis example 16-3. [compound 375] synthesis

[375]

[Intermediate 16-a] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, and [Intermediate 16-b] was used instead of [Intermediate 1-d] [Compound 375] was obtained by synthesizing in the same manner except that . (Yield 55%)

MS (MALDI-TOF): m/z 633.24 [M] ⁺

Synthesis example 17. [Compound 414] synthesis

Synthesis example 17-1. Synthesis of [Intermediate 17-a]

[17-a]

Synthesis in the same manner as in Synthesis Examples 3-1 to 3-7 using 2-bromo-9,9-diethylfluorene instead of 2-bromo-9,9-dimethylfluorene used in Synthesis Example 3-1 Thus, [Intermediate 17-a] was obtained. (Yield 57%)

Synthesis example 17-2. [compound 414] synthesis

[414]

[Intermediate 12-b] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, and [Intermediate 17-a] was used instead of [Intermediate 1-d] [Compound 414] was obtained by synthesizing in the same manner except that . (Yield 54%)

MS (MALDI-TOF): m/z 516.22 [M] ⁺

Synthesis example 18. [Compound 443] of synthesis

Synthesis example 18-1. Synthesis of [Intermediate 18-a]

[18-a]

[Intermediate 18-a] was obtained by synthesizing in the same manner as in Synthesis Examples 5-2 to 5-5 using 2,4-dimethyl-3-pentanone instead of acetone used in Synthesis Example 5-2. (Yield 52%)

Synthesis example 18-2. [compound 443] of synthesis

[443]

2-(4-bromophenyl)-4,6-diphenyl-1,3,5- instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5 [Compound 443] was obtained by synthesis in the same manner except that triazine was used and [Intermediate 18-a] was used instead of [Intermediate 1-d]. (Yield 55%)

MS (MALDI-TOF): m/z 647.29 [M] ⁺

Synthesis example 19. [Compound 474] synthesis

Synthesis example 19-1. Synthesis of [Intermediate 19-a]

[19-a]

Using 3M-ethylmagnesium bromide instead of 3M-methylmagnesium bromide used in Synthesis Example 1-2, and using [Intermediate 9-d] instead of [Intermediate 1-a], Synthesis Examples 1-2 to 1-3 and It was synthesized in the same way to obtain [Intermediate 19-a]. (Yield 55%)

Synthesis example 19-2. Synthesis of [Intermediate 19-b]

[19-b]

[Intermediate 19-a] was used instead of [Intermediate 9-f] used in Synthesis Example 9-7, and synthesized in the same manner as in Synthesis Examples 9-7 to 9-9 to obtain [Intermediate 19-b]. (Yield 67%)

Synthesis example 19-2. [compound 474] synthesis

[474]

[Intermediate 11-b] was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1-5, and [Intermediate 19-b] was used instead of [Intermediate 1-d] [Compound 474] was obtained by synthesizing in the same manner except that (yield 60%)

MS (MALDI-TOF): m/z 556.22 [M] ⁺

Example 1 to 19: Manufacturing of organic light emitting device

After patterning so that the light emitting area of the ITO glass has a size of 2 mm × 2 mm, it was washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and the organic material was placed on the ITO with HATCN (50 Å), NPD (650 Å), [BH] + Blue dopant (BD). ) 5% (200 Å), the compound prepared by the present invention (300 Å), Liq (10 Å), Al (1,000 Å) was formed into a film in this order, and the measurement was performed at 0.4 mA. The structures of [HATCN], [NPD], [BD], [BH], and [Liq] are as follows.

[HATCN] [NPD] [BD]

[BH] [Liq]

comparative example One

The organic light emitting diode device for Comparative Example 1 was manufactured in the same manner except that ET, which is generally used as an electron transport layer material, was used instead of the compound prepared by the invention in the device structure of the above embodiment, and the structure of the ET is as follows. .

[ET]

For the organic electroluminescent devices manufactured according to Examples 1 to 19 and Comparative Example 1, voltage, luminance, color coordinates and lifetime were measured, and the results are shown in Table 1 below. Here, T95 denotes the time required for the luminance to decrease to 95% compared to the initial luminance (2000 cd/m 2 ).

division ETL V Cd/A CIEx CIEy T ₉₅ (Hrs) Comparative Example 1 ET 4.2 6.4 0.133 0.129 16 Example 1 compound 1 3.6 8.0 0.132 0.130 35 Example 2 compound 5 3.6 7.9 0.133 0.128 43 Example 3 compound 71 3.4 8.0 0.132 0.126 40 Example 4 compound 72 3.8 7.9 0.133 0.125 36 Example 5 compound 164 3.3 7.6 0.132 0.126 34 Example 6 compound 167 3.9 7.6 0.133 0.125 45 Example 7 compound 197 4.0 7.5 0.133 0.125 42 Example 8 compound 200 3.6 8.1 0.132 0.130 37 Example 9 compound 233 3.4 8.0 0.133 0.128 37 Example 10 compound 234 3.6 7.8 0.133 0.127 34 Example 11 compound 293 3.6 8.0 0.132 0.130 45 Example 12 compound 313 3.6 7.9 0.133 0.128 42 Example 13 compound 329 3.4 8.0 0.132 0.126 40 Example 14 compound 341 3.8 7.9 0.133 0.125 34 Example 15 compound 370 3.3 8.0 0.132 0.126 38 Example 16 compound 375 3.9 7.9 0.133 0.125 40 Example 17 compound 414 4.0 7.6 0.132 0.126 33 Example 18 compound 443 3.6 7.6 0.133 0.125 37 Example 19 compound 474 3.7 7.5 0.133 0.125 41

As shown in [Table 1], it can be seen that the organic compound secured by the present invention has higher efficiency, lower driving voltage, and longer lifespan than ET, which is often used as an electron transport layer material. It shows that it can be used in the manufacture of a light emitting device.

Claims (7)

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

In the [Formula I],
L is a linking group, a single bond or a substituted or unsubstituted C 1 to C 30 alkylene group, a substituted or unsubstituted C 2 to C 30 alkenylene group, a substituted or unsubstituted C 2 to C 30 alkynylene group, substituted Or an unsubstituted cycloalkylene group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted C2 to 30 carbon atoms Any one selected from the heteroarylene group of
n is an integer of 1 to 3, and when L is plural, each is the same as or different from each other,
HAr ₂ is any one selected from the following [Structural Formula A] to [Structural Formula E],
[Formula A] [Formula B]

[Formula C] [Formula D]

[Structural Formula E]

In the [Structural Formula A] to [Structural Formula E],
X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, X5 is CR15 or N, X6 is CR16 or N, X7 is CR17 or N, X8 is CR18 or N, X9 is CR19 or N, X10 is CR20 or N;
At least two of X1 to X4 are selected from CR11 to CR14, and at least three of X5 to X10 are selected from CR15 to CR20,
One of X1 to X10 is a carbon atom connected to L,
R1, R2 and R11 to R20 are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted an alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 of an arylthioxy group, a substituted or unsubstituted C1 to C30 alkylamine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted and a heteroaryl group having 2 to 50 carbon atoms having O, N or S as a heteroatom, a substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 24 carbon atoms, an amino group, thi Any one selected from an ol group, a cyano group, a hydroxyl group, a nitro group, and a halogen group,
HAr ₁ is any one selected from the following [Structural Formula E1] to [Structural Formula E33],

In the [Structural Formula E1] to [Structural Formula E33],
Z ₁ to Z ₈ are the same as or different from each other, and each independently have the same definitions as R1, R2, and R11 to R20. According to claim 1,
'Substitution' in 'substituted or unsubstituted' means deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms. , C2-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 arylalkyl group, C2-C24 heteroaryl group or C2-C24 heteroarylalkyl group , C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 heteroarylamino group, C1-C24 alkylsilyl group, C6-C24 arylsilyl An organic light-emitting compound that is substituted with one or more substituents selected from the group consisting of a group, an aryloxy group having 6 to 24 carbon atoms. delete 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 564]:

a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by [Formula I] according to claim 1 . 6. The method of claim 5,
The organic layer is an organic light emitting device, characterized in that one layer or a plurality of layers selected from a light emitting layer, an electron transport layer, a hole transport layer, an electron injection layer, a hole injection layer, a hole blocking layer and an electron blocking layer. 7. The method of claim 6,
An organic light emitting device comprising a compound represented by the [Formula I] in the electron transport layer or the electron injection layer.