KR102066709B1 - Pyrene derivatives having substituted groups and organic light-emitting diode including the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device comprising the same as a light emitting material, specifically the novel compound represented by the following [Formula A] or [Formula B] and an organic electroluminescent device comprising the same It is done.
[Formula A] [Formula B]

Description

Pyrene derivative compounds having a substituent and an organic light emitting device comprising the same {Pyrene derivatives having substituted groups and organic light-emitting diode including the same}

The present invention relates to a pyrene derivative compound having a substituent and an organic light emitting device comprising the same as a light emitting material, and more particularly, excellent light emission characteristics such as driving voltage, current efficiency, longer life and stable anthracenyl It relates to a pyrene derivative compound having a group and an organic light emitting device comprising the same.

Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has a merit of being lighter than a conventional cathode ray tube (CRT). The disadvantage is that the angle is limited and the back light is necessary. In contrast, organic light emitting diodes (OLEDs), which are new flat panel display devices, are displays using self-luminous phenomena, and have a large viewing angle, are thinner and shorter than liquid crystal displays, and have fast response speeds. In recent years, the application to full-color display or lighting is expected.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.

An organic light emitting display device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, 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, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such organic light emitting diodes are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

The material used as the organic material layer in the organic electroluminescent 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 and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.

The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

In order for the organic electroluminescent device to fully exhibit the above-mentioned excellent features, the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. is supported by a stable and efficient material Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Therefore, the development of new materials in the art continues to be required.

Therefore, the first technical problem to be achieved by the present invention is to provide a pyrene derivative compound for an organic light emitting device having a long life, low drive voltage and excellent luminous efficiency.

The second technical problem to be achieved by the present invention is to provide an organic light emitting device comprising the pyrene derivative compound.

The present invention provides a pyrene derivative compound having a cyclic amine substituent represented by the following [Formula A] or [Formula B] to achieve the first technical problem.

[Formula A]

[Formula B]

In [Formula A] and [Formula B],

R ₁ to R ₄ , R ₆ to R ₉ are the same as or different from each other, and each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-30 alkyl group, a substituted or unsubstituted C2-30 Alkenyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms 6 To 30 aryloxy group, substituted or unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 arylthioxy group, substituted or unsubstituted C1-C30 alkylamine group, substituted Or an unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroa group having 3 to 50 carbon atoms having O, N or S as a hetero atom Groups, substituted or unsubstituted silicone groups, substituted or unsubstituted boron groups, substituted or unsubstituted silane groups, carbonyl groups, phosphoryl groups, amino groups, nitrile groups, hydroxy groups, nitro groups, halogen groups, amide groups and ester groups It is selected from the group consisting of, and can form a condensed ring of aliphatic, aromatic, aliphatic or aromatic hetero groups with adjacent groups,

R ₅ and R ₁₀ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon group having 3 to 30 carbon atoms A cycloalkyl group, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted hetero having 3 to 50 carbon atoms having O, N or S as a hetero atom Selected from the group consisting of an aryl group, a substituted or unsubstituted silicone group, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero group with adjacent groups;

Y ₁ to Y ₄ , Y ₆ to Y ₉ are the same as or different from each other, and each independently, have the same substituent as defined in R ₁ to R ₄ , R ₆ to R ₉ , or the following [Formula 1] It may have a substituent represented by

However, in [Formula A], at least one of Y ₄ and Y ₉ is a substituent represented by the following [Formula 1],

In addition, in [Formula B], at least one of the Y ₁ to Y ₃ and Y ₆ to Y ₈ is a substituent represented by the following [formula 1].

[Formula 1]

In the above [formula 1],

X ₁ to X ₁₀ are the same as or different from each other, and each independently composed of the same substituents as defined in R ₁ to R ₄ , R ₆ to R ₉ , wherein one of X ₁ to X ₁₀ is the following [Formula 2] It is a substituent represented by.

[Formula 2]

In the above [formula 2],

L ₁ is a linking group which is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon having 2 to 60 carbon atoms. Alkenylene group, substituted or unsubstituted C2-C60 alkynylene group, substituted or unsubstituted C3-C60 cycloalkylene group, substituted or unsubstituted C2-C60 heterocycloalkylene group, substituted or unsubstituted A substituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted hetero arylene group having 2 to 60 carbon atoms;

* Means a binding site of a pyrene group and an anthracene group in [Formula A] or [Formula B].

The present invention also includes a first electrode, a second electrode facing the first electrode and an organic layer interposed between the first electrode and the second electrode to achieve the second object, the organic layer is [ Provided is an organic light emitting device comprising at least one pyrene derivative compound represented by Formula A] or [Formula B].

According to the present invention, since the pyrene derivative compound represented by [Formula A] or [Formula B] has a stable and excellent luminescence property compared to the existing material, the organic light emitting diode including the same can be driven at a low voltage and improves the luminous efficiency. You can.

1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.

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

In order to unify the terms relating to the moieties to be substituted on the pyrene derivatives described below, the number of moieties that can be substituted with hydrogen bonded to the aromatic carbon of the pyrene group in the present invention is defined as follows.

The present invention is a pyrene derivative compound included in the light emitting layer of the organic field device, characterized in that the compound represented by the following [Formula A] or [Formula B], in [Formula A] or [Formula B], the substituent More specifically, it is as follows.

[Formula A]

[Formula B]

In [Formula A] and [Formula B],

R ₁ to R ₄ , R ₆ to R ₉ are the same as or different from each other, and each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-30 alkyl group, a substituted or unsubstituted C2-30 Alkenyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms 6 To 30 aryloxy group, substituted or unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 arylthioxy group, substituted or unsubstituted C1-C30 alkylamine group, substituted Or an unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroa group having 3 to 50 carbon atoms having O, N or S as a hetero atom Groups, substituted or unsubstituted silicone groups, substituted or unsubstituted boron groups, substituted or unsubstituted silane groups, carbonyl groups, phosphoryl groups, amino groups, nitrile groups, hydroxy groups, nitro groups, halogen groups, amide groups and ester groups It is selected from the group consisting of, and can form a condensed ring of aliphatic, aromatic, aliphatic or aromatic hetero groups with adjacent groups,

R ₅ and R ₁₀ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon group having 3 to 30 carbon atoms A cycloalkyl group, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted hetero having 3 to 50 carbon atoms having O, N or S as a hetero atom Selected from the group consisting of an aryl group, a substituted or unsubstituted silicone group, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero group with adjacent groups;

Y ₁ to Y ₄ , Y ₆ to Y ₉ are the same as or different from each other, and each independently, have the same substituent as defined in R ₁ to R ₄ , R ₆ to R ₉ , or the following [Formula 1] It may have a substituent represented by

However, in [Formula A], at least one of Y ₄ and Y ₉ is a substituent represented by the following [Formula 1],

In addition, in [Formula B], at least one of the Y ₁ to Y ₃ and Y ₆ to Y ₈ is a substituent represented by the following [formula 1].

[Formula 1]

In the above [formula 1],

X ₁ to X ₁₀ are the same as or different from each other, and each independently composed of the same substituents as defined in R ₁ to R ₄ , R ₆ to R ₉ , wherein one of X ₁ to X ₁₀ is the following [Formula 2] It is a substituent represented by.

[Formula 2]

In the above [formula 2],

L ₁ is a linking group which is a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon having 2 to 60 carbon atoms. Alkenylene group, substituted or unsubstituted C2-C60 alkynylene group, substituted or unsubstituted C3-C60 cycloalkylene group, substituted or unsubstituted C2-C60 heterocycloalkylene group, substituted or unsubstituted A substituted arylene group having 6 to 60 carbon atoms or a substituted or unsubstituted hetero arylene group having 2 to 60 carbon atoms;

* Means a binding site of a pyrene group and an anthracene group in [Formula A] or [Formula B].

In the present invention, the term "substituted or unsubstituted" is cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, arylsilyl, aryl Substituted or unsubstituted with one or more substituents selected from the group consisting of oxy group, aryl group, heteroaryl group, germanium, phosphorus, boron, hydrogen and deuterium.

More specifically, X ₁ to X ₁₀ of [Formula 1] are each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. , Substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted phenyl group, substituted or unsubstituted pentalenyl group, substituted or unsubstituted Indenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted azulenyl, substituted or unsubstituted heptalenyl, substituted or unsubstituted indaneyl ), Substituted or unsubstituted acenaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenenenyl, substituted or unsubstituted phenanthrenyl, Substituted or unsubstituted Trinyl (anthryl), substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted Cry Censenyl, substituted or unsubstituted naphthacenyl, Substituted or unsubstituted picenyl, Substituted or unsubstituted perylenyl, Substituted or unsubstituted pentaxenyl (pentaphenyl), substituted or unsubstituted hexacenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl , Substituted or unsubstituted imidazolinyl, substituted or unsubstituted imidazopyridinyl, substituted or unsubstituted imidazopyrimidinyl, substituted or unsubstituted pyridinyl group (pyridinyl), substituted or unsubstituted Pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted indolyl, substituted or unsubstituted purinyl, substituted or unsubstituted quinolinyl group ( quinolinyl), substituted or unsubstituted phthalazinyl, substituted or unsubstituted indolinzinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted quinazolinyl group ( quinazolinyl), substituted or unsubstituted cinolinyl, substituted or unsubstituted indazolyl (indazolyl), substituted or unsubstituted carbazolyl, substituted or unsubstituted phenazinyl group , Substituted or unsubstituted phenanthridinyl, substituted or unsubstituted pyranyl, substituted or unsubstituted chromenyl, substituted or unsubstituted furanyl group, substituted or unsubstituted Benzofuranyl, chi Or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted benzoimidazolyl, substituted or unsubstituted Unsubstituted isoxazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzopuranyl, substituted or unsubstituted triazinyl, or substituted Or an unsubstituted oxadiazolyl group.

More specifically, X ₁ to X ₁₀ of the [Formula 1] are each independently hydrogen; heavy hydrogen; Halogen atom; Hydroxyl group; Cyano group; Nitro group; Amino group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; Substituted or unsubstituted C2-C20 alkynyl group; A substituent of Formulas 4A to 4H; It may be a pyrene-based derivative selected from.

In Chemical Formulas 4A to 4H,

Z ₁ to Z ₇ are independently of each other, hydrogen; heavy hydrogen; Halogen atom; Hydroxyl group; Cyano group; Nitro group; Amino group; Amidino groups; Hydrazine; Hydrazone; Carboxyl groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid or salts thereof; An alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; Alkylthio groups having 1 to 10 carbon atoms; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof and phosphoric acid or salt thereof having 1 to 10 carbon atoms An alkyl group, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms; Phenyl group; Naphthyl group; Fluorenyl group; Phenanthrenyl group; Anthryl group; Pyrenyl group; Chrysenyl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group having 1 to 10 carbon atoms, carbon number 1 Phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthryl group, pyrenyl group and chrysenyl group substituted with at least one of alkoxy group having 10 to 10 and alkylthio group having 1 to 10 carbon atoms; Indolyl group; Benzimidazolyl group; Carbazolyl groups; Imidazolyl group; Imidazolinyl group; Imidazopyridinyl group; Imidazopyrimidinyl group; Pyridinyl group; Pyrimidinyl groups; Triazinyl group; Quinolinyl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group having 1 to 10 carbon atoms, carbon number 1 Indolyl group, benzoimidazolyl group, carbazolyl group, imidazolyl group, imidazolinyl group, imidazopyridinyl group substituted with at least one of an alkoxy group having 10 to 10, an alkylthio group having 1 to 10 carbon atoms, and a naphthyl group , Imidazopyrimidinyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and quinolinyl group; Di (alkyl having 1 to 10 carbon atoms) amino group; And a di (aryl having 1 to 10 carbon atoms) amino group, wherein the aryl group having 6 to 10 carbon atoms is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenyl group It is any one selected from.

)로 표시되는 치환기일 수 있다. In the present invention, the substituent X ₁₀ in the formula 1 is represented by the formula 2 (

It may be a substituent represented by).

)로 표시되는 치환기인 경우, 상기 구조식 2의 L₁ 은 단일 결합, 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 펜타레닐렌기, 치환 또는 비치환된 인데닐렌기, 치환 또는 비치환된 나프틸렌기, 치환 또는 비치환된 아줄레닐렌기, 치환 또는 비치환된 헵탈레닐렌기, 치환 또는 비치환된 인다세닐렌기, 치환 또는 비치환된 아세나프틸렌기, 치환 또는 비치환된 플루오레닐렌기, 치환 또는 비치환된 페나레닐렌기, 치환 또는 비치환된 페난트레닐렌기, 치환 또는 비치환된 안트릴렌기, 치환 또는 비치환된 플루오란테닐렌기, 치환 또는 비치환된 트리페닐레닐렌기, 치환 또는 비치환된 파이레닐렌기, 치환 또는 비치환된 크라이세닐렌기, 치환 또는 비치환된 나프타세닐렌기, 치환 또는 비치환된 피세닐렌기, 치환 또는 비치환된 페릴레닐렌기, 치환 또는 비치환된 펜타세닐렌기, 치환 또는 비치환된 헥사세닐렌기, 치환 또는 비치환된 피롤일렌기, 치환 또는 비치환된 피라졸일렌기, 치환 또는 비치환된 이미다졸일렌기, 치환 또는 비치환된 이미다졸리닐렌기, 치환 또는 비치환된 이미다조피리디닐렌기, 치환 또는 비치환된 이미다조피리미디닐렌기, 치환 또는 비치환된 피리디닐렌기, 치환 또는 비치환된 피라지닐렌기, 치환 또는 비치환된 피리미디닐렌기, 치환 또는 비치환된 인돌일렌기, 치환 또는 비치환된 푸리닐렌기, 치환 또는 비치환된 퀴놀리닐렌기, 치환 또는 비치환된 프탈라지닐렌기, 치환 또는 비치환된 인돌리지닐렌기, 치환 또는 비치환된 나프티리디닐렌기, 치환 또는 비치환된 퀴나졸리닐렌기, 치환 또는 비치환된 시놀리닐렌기, 치환 또는 비치환된 인다졸일렌기, 치환 또는 비치환된 카바졸일렌기, 치환 또는 비치환된 페나지닐렌기, 치환 또는 비치환된 페난트리디닐렌기, 치환 또는 비치환된 파이라닐렌기, 치환 또는 비치환된 크로메닐렌기, 치환 또는 비치환된 푸라닐렌기, 치환 또는 비치환된 벤조푸라닐렌기, 치환 또는 비치환된 티오페닐렌기, 치환 또는 비치환된 벤조티오페닐렌기, 치환 또는 비치환된 이소티아졸일렌기, 치환 또는 비치환된 벤조이미다졸일렌기, 치환 또는 비치환된 이속사졸일렌기, 치환 또는 비치환된 디벤조티오페닐렌기, 치환 또는 비치환된 디벤조푸라닐렌기, 치환 또는 비치환된 트리아지닐렌기, 또는 치환 또는 비치환된 옥사디아졸일렌기 중에서 선택되는 어느 하나일 수 있다.In the present invention, the substituent X ₁₀ is represented by the formula 2 (

In the case of a substituent represented by the above), L ₁ of the formula 2 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentarenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naph Tylene group, substituted or unsubstituted azulenylene group, substituted or unsubstituted heptalylene group, substituted or unsubstituted indasenylene group, substituted or unsubstituted acenaphthylene group, substituted or unsubstituted fluorenylene group , Substituted or unsubstituted phenenarenylene group, substituted or unsubstituted phenanthrenylene group, substituted or unsubstituted anthylene group, substituted or unsubstituted fluoranthhenylene group, substituted or unsubstituted triphenylenylene group, substituted Or an unsubstituted pyrenylene group, a substituted or unsubstituted chrysenylene group, a substituted or unsubstituted naphthaceylene group, a substituted or unsubstituted pisenylene group, a substituted or unsubstituted perenylene group, a substituted or Unsubstituted pentasenylene group, substituted or unsubstituted hexasenylene group, substituted or unsubstituted pyrroylene group, substituted or unsubstituted pyrazolylene group, substituted or unsubstituted imidazoleylene group, substituted or unsubstituted already Dazolinylene group, substituted or unsubstituted imidazopyridinylene group, substituted or unsubstituted imidazopyrimidinylene group, substituted or unsubstituted pyridinylene group, substituted or unsubstituted pyrazinylene group, substituted or unsubstituted A substituted pyrimidinylene group, a substituted or unsubstituted indolylene group, a substituted or unsubstituted furinylene group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted phthalazinylene group, a substituted or unsubstituted group Indolizinylene group, substituted or unsubstituted naphthyridinylene group, substituted or unsubstituted quinazolinylene group, substituted or unsubstituted cynolinylene group, substituted or unsubstituted indazoleylene group, substituted or unsubstituted Basolylene group, substituted or unsubstituted phenazinylene group, substituted or unsubstituted phenantridinylene group, substituted or unsubstituted pyranylene group, substituted or unsubstituted chromemenylene group, substituted or unsubstituted furanylene group , Substituted or unsubstituted benzofuranylene group, substituted or unsubstituted thiophenylene group, substituted or unsubstituted benzothiophenylene group, substituted or unsubstituted isothiazolylene group, substituted or unsubstituted benzoimidazolylene group , Substituted or unsubstituted isoxazolylene group, substituted or unsubstituted dibenzothiophenylene group, substituted or unsubstituted dibenzofuranylene group, substituted or unsubstituted triazinylene group, or substituted or unsubstituted oxadia It may be any one selected from solylene groups.

In this case, L ₁ of Formula 2 may be a single bond.

More specifically, in the present invention, only one selected from the substituents Y ₄ and Y ₉ in [Formula A] is a substituent represented by the above [Formula 1], and in the above [Formula B], the substituents Y ₁ to Y ₃ and Y ₆ Only one selected from Y ₈ may be a substituent represented by the above [Formula 1].

As another specific example, in [Formula A], the substituents Y ₄ and Y ₉ are each represented by the above [Formula 1], and in [Formula B], any one selected from Y ₁ to Y ₃ and Y ₆ to Any one selected from Y ₈ may be substituted with the above [formula 1].

More specifically, in the present invention, the [formula 1] in the formula (A) and formula (B) may be any one selected from the group represented by the following [substituent 1] to [substituent 100].

[Substituent 1] [substituent 2] [substituent 3]

[Substituent 4] [substituent 5] [substituent 6]

[Substituent 7] [substituent 8] [substituent 9]

[Substituent 10] [substituent 11] [substituent 12]

[13 substituents] [14 substituents] [15 substituents]

[Substituent 16] [substituent 17] [substituent 18]

[Substituent 19] [substituent 20] [substituent 21]

[Substitution 22] [Substitution 23] [Substitution 24]

[Substitution 25] [Substitution 26] [Substitution 27]

[28 substituents] [29 substituents] [30 substituents]

[Substitution 31] [Substitution 32] [Substitution 33]

[Substituent 34] [substituent 35] [substituent 36]

[Substitution 37] [Substitution 38] [Substitution 39]

[Substitution 40] [Substitution 41] [Substitution 42]

[43 substituent] [44 substituent] [45 substituent]

[Substituent 46] [Substituent 47] [Substituent 48]

[Substituent 49] [Substituent 50] [Substituent 51]

[Substitution 52] [Substitution 53] [Substitution 54]

[Substituent 55] [Substituent 56] [Substituent 57]

[Substitution 58] [Substitution 59] [Substitution 60]

[Substituent 61] [Substituent 62] [Substituent 63]

[Substituent 64] [Substituent 65] [Substituent 66]

[Substitution 67] [Substitution 68] [Substitution 69]

[Substitution 70] [Substitution 71] [Substitution 72]

[73 substituents] [74 substituents] [75 substituents]

[Substitution 76] [Substitution 77] [Substitution 78]

[Substituent 79] [substituent 80] [substituent 81]

[Substitution 82] [Substitution 83] [Substitution 84]

[Substitution 85] [Substitution 86] [Substitution 87]

[Substitution 88] [Substitution 89] [Substitution 90]

[Substitution 91] [Substitution 92] [Substitution 93]

[Substitute 94] [Substitute 95] [Substitute 96]

[Substitute 97] [Substitute 98] [Substitute 99]

[100 substituents]

More specifically, when the structural formula 1 in the pyrene-based derivative of the present invention is represented by any one selected from the group represented by the [substituent 1] to [substituent 100], the substituents R ₅ and R ₁₀ is the same as or different from each other, and each independently may be any one selected from methyl group, ethyl group, propyl group, butyl group, cyclopentyl group, cyclohexyl group, and phenyl group.

Structural formula 1 of the present invention is an anthracene ring having a substituent, the substituent may be fused with a neighboring substituent to generate a ring.

Meanwhile, the anthracenyl group of Structural Formula 1 may be bonded to a pyrene group with L ₁ interposed therebetween.

In this case, by controlling the energy band gap of the condensed cyclic compound by the L1 it is possible to adjust the emission wavelength.

When driving the organic light emitting device employing such a condensed cyclic compound between a pair of electrodes (anode and cathode), the condensed cyclic compound is generated in the organic layer between the pair of electrodes, between the organic layers or between the organic layer and the electrode. Since the organic light emitting device employing the condensed cyclic compound may have excellent driving voltage, efficiency, brightness, and lifespan.

Hereinafter will be briefly described a method for producing a pyrene-based derivative of the present invention.

Compounds of the formula [A] of the present invention can be prepared through the following schemes 1 and 2.

Scheme 1

(중간체A)

(Intermediate A)

Scheme 2

[화학식 A] (Intermediate A) + anthracene derivative

[Formula A]

As the anthracene derivative reacted with the intermediate A, a boric acid compound in which boron is bonded to a substituent of Structural Formula 1 defined in Chemical Formula A of the present invention may be used.

Accordingly, the compound of Formula A of the present invention may provide a pyrene derivative including an anthracenyl group having at least one substituent of Structural Formula 1 by substituting anthracenyl group for at least one of halogens at positions 4 and 9 of pyrene. Can be.

In addition, the compound of Formula A of the present invention may have a substituent except for hydrogen or deuterium at positions 5 and 10 of pyrene, and also includes pyrene when including two substituents in a phenyl group of a biphenyl compound which is a precursor of intermediate A. There is an advantage in that the positions 1 to 3 or 6 to 8 of can be substituted with a substituent other than hydrogen.

If the substituent substituted in the two phenyl groups of the biphenyl compound which is the precursor of the intermediate A is halogen, the compound of Formula A may have three or more amine groups of the formula (1).

On the other hand, the compound of [Formula B] of the present invention can be prepared through the following Scheme 3 and Scheme 4.

Scheme 3

(중간체B)

(Intermediate B)

Scheme 4

[화학식 B] (Intermediate B) + anthracene derivative

[Formula B]

As the anthracene derivative reacted with the intermediate B, a boric acid compound in which boron is bonded to a substituent of Structural Formula 1 defined in Chemical Formula B of the present invention may be used.

Therefore, the compound of [Formula B] of the present invention may have a substituent except for hydrogen or deuterium at positions 5 and 10 of pyrene, and also two phenyl groups of the biphenyl compound which is a precursor of intermediate B include a halogen substituent. When the at least one of the positions 1 to 3 or 6 to 8 of the pyrene is substituted by the anthracenyl group of the formula 1, it is possible to provide a pyrene derivative including an anthracenyl group having at least one substituent of the formula (1). .

In addition, the present invention is a first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one pyrene-based derivative compound of the present invention.

In the present invention, "(organic layer) comprises at least one pyrene-based derivative compound" means that "(organic layer) belongs to one pyrene-based derivative compound belonging to the scope of the present invention or one of the pyrene-based derivative compounds. May include two or more different condensed cyclic compounds. "

In this case, the organic layer containing the compound of the present invention is preferably a light emitting layer interposed between the first electrode and the second electrode, the organic layer, a hole injection layer, a hole transport layer, a hole injection function and a hole transport function It may further include at least one of a functional layer, a light emitting layer, an electron transport layer, and an electron injection layer having at the same time.

In the present invention, the organic layer includes at least one of a hole injection layer, a hole transport layer, a hole injection function and a hole transport function at the same time having a functional layer (hereinafter referred to as "H-functional layer") The condensed cyclic compound is included in at least one of a functional layer having a hole injection layer, a hole transport layer, a hole injection function, and a hole transport function (hereinafter, referred to as an “H-functional layer”). There may be.

The condensed cyclic compound included in the emission layer may serve as a fluorescent dopant. For example, the condensed cyclic compound may serve as a blue fluorescent dopant emitting blue light. Alternatively, the condensed cyclic compound included in the emission layer may serve as a fluorescent or phosphorescent host emitting red light, green light or blue light.

The 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, the organic electroluminescent device It can be used for a display element, a display element, or a element for monochrome or white illumination.

As a specific example of the present invention, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic light emitting layer. The hole transport layer is laminated in order to easily inject holes from the anode. As the material of the hole transport layer, electron donating molecules having a small ionization potential are used, mainly diamine, triamine or tetra having a basic skeleton of triphenylamine. Many amine derivatives are used.

The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. 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 (a-NPD) and the like can be used.

A hole injection layer (HIL) may be further stacked on the lower portion of the hole transport layer. The hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc (copperphthalocyanine) or starburst amines TCTA (4,4 ', 4 "-tri (N-carbazolyl) triphenyl-amine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenyl amino) triphenylamine) and the like can be used.

In addition, the electron transport layer used in the organic electroluminescent device according to the present invention has the opportunity to recombine in the light emitting layer by smoothly transporting the electrons supplied from the cathode to the organic light emitting layer and suppressing the movement of holes not bonded in the organic light emitting layer. Serves to increase.

The electron transport layer material may be used without particular limitation as long as it is commonly used in the art, and for example, oxadiazole derivatives such as PBD, BMD, BND or Alq ₃ may be used.

Meanwhile, an electron injection layer (EIL) may be further stacked on the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, materials such as LiF, NaCl, CsF, Li ₂ O, BaO and the like can be used.

The organic light emitting display device according to the present invention can be used for a display device, a display device and a monochrome or white lighting device.

1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and if necessary, the hole injection layer 30 and The electron injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to Figure 1 with respect to the organic light emitting device and a method of manufacturing the present invention are as follows. First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the anode electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30.

Subsequently, the organic light emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method. can do. The hole blocking layer prevents such a problem by using a material having a very low highest Occupied Molecular Orbital (HOMO) level because when the hole is introduced into the cathode through the organic light emitting layer is reduced the lifetime and efficiency of the device. . In this case, the hole blocking material to be used is not particularly limited, but should have an ionization potential higher than the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a cathode forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form a cathode 80 electrode. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

According to another embodiment of the present invention, 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 is a single molecule deposition method or a solution process The organic light emitting display device according to the present invention may be used in display devices, display devices, and monochrome or white lighting devices.

In addition, the light emitting layer may further include a dopant, and the compound of the present invention included in the light emitting layer may serve as a host.

In addition, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 kPa, and the light emitting layer may further include various dopant materials.

In this case, the dopant may be a compound represented by <Formula 1> or <Formula 2>.

<Formula 1>

In Formula 1,

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted, any one selected from a heteroarylene group having 3 to 50 carbon atoms having O, N or S as a hetero atom,

X1 and X2 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X1 and X2 may be bonded to each other,

l and m are each an integer of 1 to 20, n is an integer of 1 to 4,

Y1 to Y2 are each independently substituted or unsubstituted aryl group having 6 to 24 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, substituted or unsubstituted A heteroalkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, a cyano group, a halogen group, a substituted or unsubstituted carbon group having 6 to 24 carbon atoms At least one selected from the group consisting of an aryloxy group, a substituted or unsubstituted C1-C40 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, germanium, phosphorus, boron, deuterium and hydrogen And each of Y 1 to Y 2 is the same as or different from each other, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero, or aromatic hetero group with adjacent groups.

More specifically, X1 to X2 in the <Formula 1> is substituted or unsubstituted phenylene group, substituted or unsubstituted pentalenylene group, substituted or unsubstituted indenylene group, substituted or unsubstituted naphthylene group, substituted Or an unsubstituted azulenylene group, a substituted or unsubstituted heptalylene group, a substituted or unsubstituted indasenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted group A substituted phenenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthylene group, a substituted or unsubstituted fluoranthhenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted group Pyrenylene groups, substituted or unsubstituted chrysenylene groups, substituted or unsubstituted naphthasenylene groups, substituted or unsubstituted pisenylene groups, substituted or unsubstituted peryleneylene groups, substituted or unsubstituted penta Senylene group, substituted or unsubstituted hexasenylene group, substituted or unsubstituted pyrroylene group, substituted or unsubstituted pyrazolylene group, substituted or unsubstituted imidazolylene group, substituted or unsubstituted imidazolinylene group , Substituted or unsubstituted imidazopyridinylene group, substituted or unsubstituted imidazopyrimidinylene group, substituted or unsubstituted pyridinylene group, substituted or unsubstituted pyrazinylene group, substituted or unsubstituted pyrimidy Nylene group, substituted or unsubstituted indolylene group, substituted or unsubstituted furinylene group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted phthalazinylene group, substituted or unsubstituted indoldylene group , Substituted or unsubstituted naphthyridinylene group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted cynolinylene group, substituted or unsubstituted indazolylene group, substituted or unsubstituted carbazoleylene group, Cyclic or unsubstituted phenazinylene groups, substituted or unsubstituted phenantridinylene groups, substituted or unsubstituted pyranylene groups, substituted or unsubstituted chromemenylene groups, substituted or unsubstituted furanylene groups, substituted or unsubstituted A substituted benzofuranylene group, a substituted or unsubstituted thiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted isothiazolylene group, a substituted or unsubstituted benzoimidazolylene group, a substituted or unsubstituted group Selected from a substituted isoxazolylene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted triazinylene group, or a substituted or unsubstituted oxadiazoleylene group Can be.

<Formula 2>

In <Formula 2>,

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted, any one selected from a heteroarylene group having 3 to 50 carbon atoms having O, N or S as a hetero atom,

C _y is substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form. In addition, hydrogen substituted therein may be each substituted with deuterium or alkyl, and the same or different from each other.

B is a single bond or-[C (R ₅ ) (R ₆ )] _p- , wherein p is an integer from 1 to 3, and when p is 2 or more, two or more R ₅ and R ₆ are the same or different from each other;

R ₁ , R ₂ , R _3, R ₅ and R ₆ independently of one another are hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group Salts, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, substituted or unsubstituted C1-C60 alkyl groups, substituted or unsubstituted C2-C60 alkenyl groups, substituted or unsubstituted C2-C60 alkynyl groups, Substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, substituted or unsubstituted carbon atoms 6 To 60 aryl group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted or Unsubstituted Alkyl amino group having 1 to 60 minor atoms, di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms), or (substituted or unsubstituted aryl having 6 to 60 carbon atoms), di (substituted or unsubstituted carbon atoms having 6 to 60 carbon atoms Aryl) amino group of 60, substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms;

n is an integer from 1 to 4;

is a case of being an integer of 1 to 4, a is 2 or more at least two R ₃ are the same or different, R ₃ together with a plurality, and each R ₃ may be been fused form.

More specifically, R ₁ , R ₂ and R ₃ of <Formula 2> are each independently hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone , Carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C1-20 alkyl group, substituted or unsubstituted C1-20 alkenyl group, substituted or unsubstituted C2-20 An alkynyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted group Azulenyl, substituted or unsubstituted heptalenyl, substituted or unsubstituted indacenyl, substituted or unsubstituted acenaphthyl, substituted or unsubstituted fluorenyl group ( fluorenyl), substituted or Substituted phenalenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted anthryl groups, substituted or unsubstituted fluoranthenyl groups, substituted or unsubstituted Triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted naphthacenyl, substituted or unsubstituted Picenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted pentasenyl group, substituted or unsubstituted hexacenyl group, substituted or unsubstituted pyrroylyl group (pyrrolyl), substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted imidazolinyl, substituted or unsubstituted imidazopyridi An imidazopyridinyl, substituted or unsubstituted Imidazopyrimidinyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted Indolyl, substituted or unsubstituted purinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted phthalazinyl, substituted or unsubstituted indolinyl Indolizinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted cinolinyl, substituted or unsubstituted indazolyl groups ( indazolyl), substituted or unsubstituted carbazolyl, substituted or unsubstituted phenazinyl group, substituted or unsubstituted phenanthridinyl group, substituted or unsubstituted pyranyl group ), Substituted or unsubstituted Romenyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted Or unsubstituted isothiazolyl, substituted or unsubstituted benzoimidazoyl, substituted or unsubstituted isoxazolyl, substituted or unsubstituted dibenzothiophenyl, It may be selected from the group consisting of a substituted or unsubstituted dibenzopuranyl group, a substituted or unsubstituted triazinyl group, or a substituted or unsubstituted oxadiazolyl group (oxadiazolyl).

More specifically, R ₁ , R _2, and R ₃ of [Formula 2] may be independently a substituent represented by one of the following Formulas 4A to 4H.

In Chemical Formulas 4A to 4H,

Z ₁ to Z ₇ are independently of each other, hydrogen; heavy hydrogen; Halogen atom; Hydroxyl group; Cyano group; Nitro group; Amino group; Amidino groups; Hydrazine; Hydrazone; Carboxyl groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid or salts thereof; An alkyl group having 1 to 10 carbon atoms; An alkoxy group having 1 to 10 carbon atoms; Alkylthio groups having 1 to 10 carbon atoms; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof and phosphoric acid or salt thereof having 1 to 10 carbon atoms An alkyl group, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms; Phenyl group; Naphthyl group; Fluorenyl group; Phenanthrenyl group; Anthryl group; Pyrenyl group; Chrysenyl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group having 1 to 10 carbon atoms, carbon number 1 Phenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthryl group, pyrenyl group and chrysenyl group substituted with at least one of alkoxy group having 10 to 10 and alkylthio group having 1 to 10 carbon atoms; Indolyl group; Benzimidazolyl group; Carbazolyl groups; Imidazolyl group; Imidazolinyl group; Imidazopyridinyl group; Imidazopyrimidinyl group; Pyridinyl group; Pyrimidinyl groups; Triazinyl group; Quinolinyl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group having 1 to 10 carbon atoms, carbon number 1 Indolyl group, benzoimidazolyl group, carbazolyl group, imidazolyl group, imidazolinyl group, imidazopyridinyl group substituted with at least one of an alkoxy group having 10 to 10, an alkylthio group having 1 to 10 carbon atoms, and a naphthyl group , Imidazopyrimidinyl group, pyridinyl group, pyrimidinyl group, triazinyl group, and quinolinyl group; Di (alkyl having 1 to 10 carbon atoms) amino group; And a di (aryl having 1 to 10 carbon atoms) amino group, wherein the aryl group having 6 to 10 carbon atoms is a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthryl group, a pyrenyl group, and a chrysenyl group It is any one selected from.

Preferably B in <Formula 2> may be a single bond.

 Hereinafter, the present invention will be described in more detail with reference to preferred examples. However, these examples are intended to illustrate the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited thereby.

<Example>

Synthesis Example 1. Synthesis of Compound BD1

1-1. Dihalopyrene Intermediate Synthesis

(1-A) Synthesis of 4,9-Diiodo-5,10-diphenyl-pyrene (hereinafter referred to as 'pyrene A')

 (1-A-1) Synthesis of 2-bromobiphenylacetylene

[Scheme 5]

2-bromo-iodo-benzene (10 g, 35 mmol), Pd (PPh3) 4 (0.8 g, 0.5 mmol) and CuI (0.54 g, 1 mmol) were added to 50 mL of triethylamine and stirred at room temperature. The mixture was mixed well (the reaction proceeded in a nitrogen atmosphere), and phenylacetylene (3.6 mL, 35 mmol) was slowly added thereto.

After stirring for 1 hour at room temperature, 300 mL of hexane was added to terminate the reaction. The whole solution was passed through silica gel to separate the product, and the column was lowered to 500 mL of hexane. The solvent was removed to give a white product. (Yield 98%)

* 128MS (MALDI-TOF): m / z 257 [M] ⁺

(1-A-2) Synthesis of 2-biphenylacetylene boronic acid

Scheme 6

2-bromobiphenylacetylene (10 g, 55 mmol) was dissolved in 100 mL of THF. N-BuLi (50 mL) was added slowly while cooling to -78 ° C. After the addition, the mixture was stirred at −78 ° C. for about 1 hour, and trimethyl borate (6.57 g, 63 mmol) was added thereto. After stirring at −78 ° C. for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2 N HCl was added to adjust acidity. After extraction with EA, the solvent was removed, diluted with hexane and stirred at -78 ° C to solidify to obtain a white solid. (Yield 70%)

MS (MALDI-TOF): m / z 223 [M] ⁺

(1-A-3) Synthesis of 2,2'-diphenylethynylbiphenyl

Scheme 7

2-bromobiphenylacetylene (10 g, 55 mmol), 2-biphenylacetylene boronic acid (9.5 g, 43 mmol), K 2 CO 3 (10.75 g, 78 mmol), Pd (PPh 3) 4 (0.9 g, 1 mmol) Was added to 100 mL of toluene, 100 mL of THF, and 50 mL of H 2 O to reflux. After completion of the reaction, the organic solvent was removed by layer separation, and the product was separated by column separation (MC: Hx = 1: 9). (Yield 70%)

MS (MALDI-TOF): m / z 355 [M] ⁺

(1-A-4) Synthesis of Pyrene A

Scheme 8

Pyrene A

2,2'-diphenylethynylbiphenyl (10 g, 28 mmol) was dissolved in 100 mL of MC. 68 ml of ICl (1M in MC) was slowly added at room temperature. After stirring for 1 hour at room temperature, iodine was removed with saturated Na 2 S 2 O 3 and EA was extracted. The product was separated by column (MC: Hx = 1: 9) (yield 60%).

MS (MALDI-TOF): m / z 606 [M] ⁺

(1-B) Synthesis of 2,7-Dibromo-5,10-diphenyl-pyrene (hereinafter referred to as 'pyrene B')

(1-B-1) Synthesis of 4,4'-Dibromo-2,2'-dinitro-biphenyl.

Scheme 9

250 g (0.890 mol) of 2,5-dibromonitrobenzene, 135.74 g (2.136 mol) of copper powder and 1 L of DMF were added. The temperature of the reactor was raised to 125 ° C. and stirred for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, and 500 mL of toluene was added thereto and stirred. Insoluble inorganic salts were removed by celite filter and the filtrate was dried. 2 liters of Methanol was added to the dried filtrate and stirred vigorously. The resulting crystals were filtered and dissolved again in 500 mL of Toluene. The remaining inorganic salt was again removed by celite filter, and then the filtrate was dried. Then, MeOH was added and the mixture was stirred vigorously to recrystallize 139 g (77.7%) of 4,4'-Dibromo-2,2'-dinitro-biphenyl. Got it.

MS (MALDI-TOF): m / z 401 [M] ⁺

(1-B-2) Synthesis of 4,4'-Dibromo-2,2'-diaminobiphenyl

Scheme 10

139.7 g (0.347 mol) of 4,4'-dibromo-2,2'-dinitro-biphenyl was added thereto, followed by 2 L of ethanol. And 1 M of 12 M HCl was added and stirred. The temperature of the reactor was lowered to 0 ° C. and 165 g (1.39 mol) Tin powder was slowly added over 20 minutes. The temperature of the reactor was raised to 100 ° C. and refluxed for 3 hours. After the reaction was completed, the temperature of the reactor was lowered to 0 ° C. and 12 M 1 L of aqueous sodium hydroxide solution was added slowly to make the reaction solution basic. Ethylacetate was added to extract the organic layer, and the organic layer was anhydrous and concentrated. Hexane and methylene chloride were used as the developing solvent to separate the residue by column chromatography to obtain 4,4'-dibromo-2,2'-diaminobiphenyl. (87.7 g, 73.8%)

MS (MALDI-TOF): m / z 341 [M] ⁺

(1-B-3) Synthesis of 4,4'-Dibromo-2,2'-Diiodobiphenyl

Scheme 11

87.7 g (0.256 mol) of 4,4'-Dibromo-2,2'-diaminobiphenyl, 380 mL of 12 M HCl, and 380 mL of water were added thereto. The temperature of the reactor was lowered to 0 ° C. Sodiumnitrite 44.2 g (0.641 mol) was dissolved in 220 mL of water and slowly added dropwise to the reactor, and when the dropwise addition was completed, the mixture was stirred for 1 hour at the same temperature for 1 hour. Potassium iodide was dissolved in 850 mL of water and slowly added dropwise, and when the addition was completed, the mixture was stirred at room temperature for 1 hour. And the temperature of the reactor was heated up to 60 degreeC and stirred for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with Ethylacetate to separate the organic layer. The organic layer was dried over anhydrous and dried, and then separated by column chromatography using hexane as a developing solvent, to obtain 42.1g (29.1%) of 4,4'-dibromo-2,2'-diodiobiphenyl.

MS (MALDI-TOF): m / z 563 [M] ⁺

(1-B-4) Synthesis of 4,4'-Dibromo-2,2'-diphenylethynylbiphenyl

Scheme 12

In a 500 mL round-bottom flask, 20 g (0.036 mol) of 4,4'-Dibromo-2,2'-diiodobiphenyl, 0.7 g (0.0035 mol) of Copper iodide, 1.6 g (0.0014) of Pd (PPh3) 4 under nitrogen stream mol) and dissolved in 200 mL of Triethyl amine. 9.3 g (0.085 mol) of Phenylacetylene was slowly added dropwise to the reactor and stirred for 1 hour. After the reaction was dissolved in MC and filtered using Celite and Silica. The filtrate was dried and 13.5 g (74.3%) of 4,4'-Dibiromo-2,2'-diphenylethynylbiphenyl obtained by column chromatography using hexane as a developing solvent was obtained.

MS (MALDI-TOF): m / z 511 [M] ⁺

Synthesis of (1-B-5) pyrene B

Scheme 13

                                             Pyren B

12.3 g (0.024 mol) of 4,4'-dibromo-2,2'-diphenylethynylbiphenyl was added to a 250 mL reactor under a stream of nitrogen, and dissolved in 120 mL of dichloroethane. 1.2 g (0.002 mol) of Iron (III) trifluoro-methansulfonate was added and refluxed for 12 hours. After the reaction was terminated by hotfilter. The filtrate was dried and EA slurry. The resulting solid was filtered and recrystallized to obtain 2.0 g (16.3%) of 5,10-dibromo-2,7-diphenyl-pyrene.

MS (MALDI-TOF): m / z 511 [M] ⁺

1-2. Synthesis of Anthracene Derivatives Having Structural Formula 1

Synthesis Example 1-2-a) Synthesis of 9-phenyl Anthracene

In a 500 ml three-necked round-bottom flask, 9.7 g (79 mmol) of phenyl boric acid, 17 g (66 mmol) of 9-Bromoanthracene, 18.3 g (132 mmol) of potassium carbonate, Pd (PPh3) 4 1.5 g (1 mmol), 35 ml of water, 90 ml of toluene and 90 ml of tetrahydrofuran were added and refluxed.

After the completion of the reaction, the layers were separated, the aqueous layer was removed, the organic layer was concentrated under reduced pressure, and 13.6 g (yield 81%) of 9-phenyl anthracene was obtained using column chromatography.

Synthesis Example 1-2-b) Synthesis of 9-phenyl-10bromoanthracene

13.6 g (0.054 mol) of 9-phenylanthracene prepared in Synthesis Example 1-2-a and 272 ml of dichloromethane were dissolved in a 1 L three-necked round bottom flask, and the crystals were dissolved at room temperature, and cooled to 0 ° C., followed by bromine. 10.1 g (0.063 mol) was diluted in 50 ml of dichloromethane and reacted slowly. After completion of the reaction, the layers were separated, the aqueous layer was removed, the organic layer was concentrated under reduced pressure, crystals were precipitated with MeOH and recrystallized to obtain 13.4 g (yield 75.5%) of yellow 9-phenyl-10-bromoanthracene crystals.

Synthesis Example 1-2-c) Synthesis of 9-phenyl-10-anthraceneboronic acid

9-phenyl-10-bromoanthracene (13.4 g, 40 mmol) was dissolved in 110 mL THF. N-BuLi (30 mL) was added slowly while cooling to -78 ° C. After the addition, the mixture was stirred at −78 ° C. for about 1 hour, and trimethyl borate (5.9 g, 56 mmol) was added thereto. After stirring at −78 ° C. for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2 N HCl was added to adjust acidity. Crystals were extracted with hexane, followed by extraction with EA, and solvents were removed to obtain 9.2 g (yield 76.7%) of 9-phenyl-10-anthracene boronic acid.

1-3. Synthesis of Pyrene Derivatives BD1 Including Anthracenyl Substituents

9.2 g (31 mmol) of 9-phenyl-10-anthraceneboronic acid prepared in Synthesis Example 1-2-c, pyrene A 18.8 g (31 mmol), K ₂ CO ₃ (8.6 g, 62 mmol) in a round bottom flask , Pd (PPh ₃ ) ₄ (0.7 g, 1 mmol) was refluxed into 100 mL of toluene, 100 mL of THF, and 40 mL of water.

After the completion of the reaction, the produced crystals were filtered and recrystallized several times with toluene and acetone. The solid (5.5 g, yield 24.2%) was dried, and the dried solid (5.5 g, 8 mmol) and tetrahydrofuran 50 ml in a reactor under nitrogen stream. Was added and 5.2 mL (9 mmol) of n-BuLi was slowly added while cooling to -78 ° C while stirring. At this time, heat is generated, and after cooling to -40 ° C, 15 ml of water is quenched. Compound BD1 (1.0 g, yield 22%) was synthesized by recrystallization several times with toluene and acetone.

MS (MALDI-TOF): m / z 607 [M] ⁺

Synthesis Example 2 Synthesis of Compound BD2

Synthesis Example 1-2-a) A light yellow solid compound BD2 having 1.5 g, yield 25.4%, using the same method as the synthesis method of Compound BD1, except that 2-tolyl boronic acid was used instead of phenyl boronic acid. Got.

MS (MALDI-TOF): m / z 621 [M] ⁺

Synthesis Example 3 Synthesis of Compound BD3

Synthetic Example 1-2-a) A light yellow solid compound having a yield of 1.4 g and a yield of 25% using the same method as the synthesis method of Compound BD1, except that 1-naphthyl boronic acid was used instead of phenyl boronic acid. Obtained BD3.

MS (MALDI-TOF): m / z 657 [M] ⁺

Synthesis Example 4 Synthesis of Compound BD4

A light yellow solid having a yield of 2.3 g and a yield of 24.5% by using the same method as the synthesis of Compound BD1, except that pentaduteriophenyl boronic acid was used instead of phenyl boronic acid in Synthesis Example 1-2-a). Compound BD4 was obtained.

MS (MALDI-TOF): m / z 612 [M] ⁺

Synthesis Example 5 Synthesis of Compound BD5

A light yellow solid compound BD5 having 1.7 g and yield 21.3% was obtained in the same manner as in Synthesis Example 1-3, except that dihalopyrene intermediate was used as pyrene B.

Synthesis Example 6 Synthesis of Compound BD6

Dihalopyrene intermediates were synthesized in the same manner as in Synthesis Example 2, except that pyrene B was used to obtain 1.4 g of a light yellow solid compound BD6 having a yield of 23.5%.

Synthesis Example 7 Synthesis of Compound BD7

Synthesis Example 7-a) Synthesis of 9- (4-bromophenyl) -10-phenylanthracene

9.2 g (31 mmol) 9-phenyl-10-anthracene boronic acid, 8.7 g (31 mmol) 4-bromo-1-iodobenzene, 8.5 g (62 mmol) potassium carbonate, Pd (PPh ₃ ) ₄ 0.7 g (1 mmol), 20 ml of water, 50 ml of toluene and 50 ml of tetrahydrofuran were added and refluxed.

After the completion of the reaction, the layers were separated, the aqueous layer was removed, the organic layer was concentrated under reduced pressure, and 10.6 g (yield 84.2%) of 9- (4-bromophenyl) -10-phenylanthracene was obtained using column chromatography.

Synthesis Example 7-b) Synthesis of 4- (10-phenyl-9-anthryl) phenylboronic acid

9- (4-bromophenyl) -10-phenylanthracene (10.6 g, 26 mmol) was dissolved in 90 mL of THF. N-BuLi (19.4 mL) was added slowly while cooling to -78 ° C. After the addition, the mixture was stirred at −78 ° C. for about 1 hour, and trimethyl borate (3.8 g, 36 mmol) was added thereto. After stirring at −78 ° C. for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2 N HCl was added to adjust acidity. Crystals were extracted with hexane, followed by extraction with EA, and solvent was removed to obtain 7.4 g (yield 76.4%) of 4- (10-phenyl-9-anthryl) phenylboronic acid.

Synthesis Example 7-c) Synthesis of Compound BD7

7.4 g (20 mmol) of 4- (10-phenyl-9-anthryl) phenylboronic acid prepared in Synthesis Example 7-b in the round bottom flask, 12 g (20 mmol) of pyrene A, K ₂ CO ₃ (5.5 g , 40 mmol) and Pd (PPh ₃ ) ₄ (0.5 g, 1 mmol) were refluxed into 60 mL of toluene, 60 mL of THF, and 25 mL water.

After the completion of the reaction, the resulting crystals were filtered, and the solid (8.2 g, yield 51.2%) obtained by recrystallization several times with toluene and acetone was dried, and the dried solid (8.2 g, 10 mmol) and tetrahydrofuran in a reactor under nitrogen stream. 70 ml of n-BuLi 7.0 mL (11 mmol) was slowly added while cooling to -78 ° C while stirring. At this time, the exotherm occurs, and after cooling to -40 ℃, 20ml of water is quenched. Recrystallization several times with toluene and acetone to synthesize compound BD7 (1.6g, yield 23.1%).

MS (MALDI-TOF): m / z 683 [M] ⁺

Synthesis Example 8. Synthesis of Compound BD8

9.2 g (31 mmol) of 9-phenyl-10-anthraceneboronic acid prepared in Synthesis Example 1-2-c, 7.8 g (13 mmol) of pyrene A, K ₂ CO ₃ (3.6 g, 26 mmol) in a round bottom flask ), Pd (PPh ₃ ) ₄ (0.3 g, 1 mmol) was refluxed into 40 mL of toluene, 40 mL of 1,4-dioxane and 20 mL of water.

After the reaction was completed, the resulting crystals were filtered and recrystallized several times with toluene and acetone to synthesize a pale yellow solid compound BD8 (2.6 g, yield 25%).

MS (MALDI-TOF): m / z 859 [M] ⁺

 Examples 2 to 8

The light emitting area of the ITO glass was patterned to a size of 2 mm × 2 mm and then washed. After mounting the ITO glass in a vacuum chamber, the base pressure is 1 ㅧ 10 ^-7 torr, and then formed on the ITO in the order of CuPc (800 kPa), α-NPD (300 kPa), and then the compound according to the present invention. After film formation (250 mW), Alq ₃ (350 mW), LiF (5 mW), and Al (500 mW) were formed to form an organic light emitting display device.

Comparative example

Prepared in the same manner as in Example, except that the light emitting layer further includes, as a host compound, an anthracene-based compound represented by the following [Formula 3], and the dopant material includes one of the compounds of [Formula 4] to [Formula 6]. Selected and used.

Wherein Formula 6 is a mixture (6a: 6b = 30: 70, molar ratio) having the structures of Formulas 6a and 6b below.

[Formula 3] [Formula 4] [Formula 5]

      [Formula 6]

[Formula 6a] [Formula 6b]

Evaluation example

For the organic light emitting diodes manufactured according to Examples 1 to 22 and Comparative Examples 1 to 3, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in the following [Table 1]. T97 means the time taken for the luminance to decrease to 97% of the initial luminance.

Host
Dopant Voltage Current density (㎃ / ㎠) Luminance (Cd / ㎡) Luminous color T97 Example 1
Synthesis Example 1 Formula 4 4.2 10 810 blue 95 Example 2
Synthesis Example 2 Formula 4 4.2 10 840 blue 99 Example 3
Synthesis Example 3 Formula 4 4.1 10 830 blue 80 Example 4
Synthesis Example 4 Formula 4 4.0 10 910 blue 105 Example 5
Synthesis Example 5 Formula 4 4.3 10 780 blue 92 Example 7
Synthesis Example 7 Formula 4 4.2 0 750 blue 88 Example 8
Synthesis Example 8 Formula 4 4.2 0 820 blue 85 Comparative Example 1
Formula 3 Formula 4 6.5 10 420 blue 20 Example 9
Synthesis Example 1 Formula 5 4.1 10 720 green 110 Example 10
Synthesis Example 2 Formula 5 4.0 10 830 green 102 Example 11
Synthesis Example 3 Formula 5 4.1 10 800 green 93 Example 12
Synthesis Example 4 Formula 4 4.2 10 900 green 125 Example 13
Synthesis Example 5 Formula 5 4.1 10 730 green 100 Example 14
Synthesis Example 7 Formula 5 4.0 10 820 green 89 Example 15
Synthesis Example 8 Formula 5 4.1 10 750 green 96 Comparative Example 2
Formula 3 Formula 5 6.2 10 380 green 12 Example 16
Synthesis Example 1 Formula 6 4.3 10 780 yellow 90 Example 17
Synthesis Example 2 Formula 6 4.2 0 750 yellow 102 Example 18
Synthesis Example 3 Formula 6 4.3 10 770 yellow 89 Example 19
Synthesis Example 4 Formula 6 4.1 10 920 yellow 106 Example 20
Synthesis Example 5 Formula 6 4.2 100 750 yellow 100 Example 21
Synthesis Example 7 Formula 6 4.0 10 800 yellow 95 Example 22
Synthesis Example 8 Formula 6 3.9 10 750 yellow 88 Comparative Example 3
Formula 3 Formula 6 6.4 10 410 yellow 15

As shown in Table 1, the organic light emitting diode including the organic light emitting compound according to the present invention has a low driving voltage, and has excellent light emission characteristics such as luminance and lifetime, and thus may be used in various display devices.

10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode

Claims (16)

A pyrene derivative represented by the following [Formula B].
[Formula B]

In [Formula B],
R ₄ and R ₉ are the same as or different from each other, and each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted A substituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted and substituted as a hetero atom, O, N or S It is selected from the group consisting of a heteroaryl group, a nitrile group, a nitro group, a halogen group having 3 to 50 carbon atoms, and can form a condensed ring of an aliphatic or aromatic group and adjacent to each other,
R ₅ and R ₁₀ are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and may form a condensed ring of an aliphatic or aromatic group adjacent to each other,
Y ₁ to Y ₃ , Y ₆ to Y ₈ may be the same as or different from each other, and each independently, may be the same substituent as defined in the R ₄ and R ₉ , or have a substituent represented by the following [formula 1] Can and
Provided that Y _1, Y ₃ , Y _{6 and} Y ₈ are the same as or different from each other, and are each independently the same substituent as defined in R ₄ and R ₉ ,
At least one of Y ₂ and Y ₇ is a substituent represented by the following [formula 1].
[Formula 1]

In the above [formula 1],
X ₁ to X ₉ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen atom; Cyano group; Nitro group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituent of Formulas 4A and 4E to 4F; Displayed as one selected from Consisting of substituents,

In Chemical Formulas 4A, 4E to 4F,
Z ₁ to Z ₇ are independently of each other, hydrogen; heavy hydrogen; Halogen atom; Cyano group; Nitro group; An alkyl group having 1 to 10 carbon atoms; An alkyl group having 1 to 10 carbon atoms and an alkoxy group having 1 to 10 carbon atoms substituted with one or more of deuterium, a halogen atom, a cyano group and a nitro group; Phenyl group; Naphthyl group; Fluorenyl group; Phenanthrenyl group; Anthryl group; Pyrenyl group; Chrysenyl group; Phenyl, naphthyl, fluorenyl, phenanthrenyl, anthryl, pyrenyl and chrysenyl groups substituted with one or more of deuterium, a halogen atom, a cyano group, a nitro group and an alkyl group having 1 to 10 carbon atoms; Is any one selected from
X ₁₀ is a substituent represented by the following [Formula 2].
[Formula 2]

In the above [formula 2],
L ₁ is a linking group which is a single bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;
* Is a binding site of a pyrene group and an anthracene group in the above [Formula B];
'Substituted' in the 'substituted or unsubstituted' means substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, nitro group. delete delete delete The method of claim 1,
L ₁ of Formula 2 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted group An azulenylene group, a substituted or unsubstituted heptalenylene group, a substituted or unsubstituted indasenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenenalenyl A ethylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthylene group, a substituted or unsubstituted fluoranthhenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted pyrenylene group, Substituted or unsubstituted chrysenylene group, substituted or unsubstituted naphthacelene group, substituted or unsubstituted pisenylene group, substituted or unsubstituted perenylene group, substituted or unsubstituted pentaxenylene group, substituted Or a pyrene-based derivative, which is any one selected from an unsubstituted hexasenylene group. The method of claim 5,
Pyrene derivatives, characterized in that L _{1 in} the formula 2 is a single bond The method of claim 1,
A pyrene-based derivative, characterized in that only one selected from the substituents Y ₂ and Y ₇ is a substituent represented by the above [formula 1]. The method of claim 5,
A pyrene-based derivative, characterized in that only one selected from the substituents Y ₂ and Y ₇ is a substituent represented by the above [formula 1]. The method of claim 8,
Pyrene derivatives, characterized in that L _{1 in} the formula 2 is a single bond The method of claim 1,
[Formula 1] in Formula B is
[Substituent 1] to [substituent 10], [substituent 17], [substituent 18], [substituent 20] to [substituent 26], [substituent 36], [substituent 37], [substituent 40], [substituent 47 ] To [substituent 49], [substituent 51], [substituent 60] any one of the pyrene derivatives characterized in that.
[Substituent 1] [substituent 2] [substituent 3]

[Substituent 4] [substituent 5] [substituent 6]

[Substituent 7] [substituent 8] [substituent 9]

[10 substituents]

[Substituent 17] [substituent 18]

[Substituent 20] [substituent 21]

[Substitution 22] [Substitution 23] [Substitution 24]

[Substitution 25] [Substitution 26]

[36 substituents]

[Substituent 37] [substituent 40]

[Substituent 47] [Substituent 48]

[Substituent 49] [Substituent 51]

[Substituent 60]

The method of claim 1,
R ₅ and R ₁₀ are each a phenyl group, a pyrene derivative, characterized in that A first electrode;
A second electrode opposed to the first electrode; And
An organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises at least one pyrene-based derivative compound of any one of claims 1, 5, and 11; Light emitting element. The method of claim 12,
The organic light emitting device of claim 1, wherein the organic layer interposed between the first electrode and the second electrode is a light emitting layer. The method of claim 12,
And the organic layer comprises at least one of a functional layer having a hole injection layer, a hole transport layer, a hole injection function, and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 13,
The light emitting layer further comprises a dopant, the pyrene-based derivative compound included in the light emitting layer serves as a host, an organic light emitting device The method of claim 15,
The dopant is a compound represented by the following formula 1 or formula 2, an organic light emitting device

[Formula 1] [Formula 2]

In the above [Formula 1] and [Formula 2],
A is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms. , A substituted or unsubstituted, any one selected from a heteroarylene group having 3 to 50 carbon atoms having O, N or S as a hetero atom;
In [Formula 1],
X1 and X2 are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, and X1 and X2 may be bonded to each other;
Y1 to Y2 are each independently substituted or unsubstituted aryl group having 6 to 24 carbon atoms, substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, cyano group, halogen group , A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, deuterium and hydrogen, and each of Y1 to Y2 are the same as each other or Different, and may form condensed rings of groups, aliphatic and aromatic groups adjacent to each other;
l, m are each an integer from 1 to 20, n is an integer from 1 to 4;
In [Formula 2],
C _y is substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in fused form. In addition, the hydrogen sites in the cycloalkane may be substituted with deuterium or alkyl having 1 to 20 carbon atoms, respectively, the same as or different from each other;
B Is a single bond or-[C (R ₅ ) (R ₆ )] _p- , wherein p is an integer from 1 to 3, and when p is 2 or more, two or more R ₅ and R ₆ are the same or different from each other;
R ₁ , R ₂ , R _3, R ₅ and R ₆ are each independently hydrogen, deuterium, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted carbon number 3 to 60 cycloalkyl group, substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms to be selected Can and
a is an integer of 1 to 4, when a is 2 or more, two or more R ₃ are the same as or different from each other, and when R ₃ is a plurality, each R ₃ may be in a fused form, and n is 1 to 4 Is an integer,
'Substituted' in the 'substituted or unsubstituted' means substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, nitro group.

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