KR20190071245A - Organic compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More particularly, the present invention relates to: a novel compound having excellent light emitting ability and electron transporting ability; and the organic electroluminescent device having improved characteristics such as high luminous efficiency, low driving voltage, long lifespan and the like by comprising the same into one or more organic layers.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device using the organic compound.

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel compound having excellent light emitting ability and electron transporting ability, And an organic electroluminescent device having improved characteristics.

A study on organic electroluminescent devices that resulted in blue electroluminescence using anthracene single crystals in 1965 based on observation of organic thin film emission of Bernanose in the 1950s was conducted by Tang in 1987 divided by the functional layer of the hole layer and the light emitting layer An organic electroluminescent device having a laminated structure has been proposed. Since then, in order to make high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form of introducing a characteristic organic material layer in the device, leading to the development of specialized materials used therefor.

In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on its function.

The light emitting layer forming material of the organic electroluminescent device can be classified into blue, green and red light emitting materials according to the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material.

The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

NPB, BCP, Alq ₃ and the like are widely known as materials used for the hole injecting layer, the hole transporting layer, the hole blocking layer and the electron transporting layer, and the anthracene derivatives as a luminescent material have been reported as a fluorescent dopant / host material . In particular Firpic, Ir as a phosphorescent material that has a great advantage in improving the efficiency aspects of the light-emitting material _{(ppy) 3, (acac)} Ir (btp) 2 Ir metal complex compound is a blue, green and red host material that includes such as . So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional luminescent materials are advantageous in terms of luminescence properties, but they are not satisfactory in terms of lifetime in an organic electroluminescent device because the glass transition temperature is low and the thermal stability is not very good. Therefore, development of a luminescent material having excellent performance is required.

Japanese Patent Application Laid-Open No. 2001-160489

In order to solve the above problems, the present invention provides a novel organic compound which can be applied to an organic electroluminescent device and has excellent hole injecting ability, hole transporting ability, light emitting ability, electron transporting ability and electron injecting ability The purpose.

It is another object of the present invention to provide an organic electroluminescent device including the novel organic compound and exhibiting a low driving voltage and a high luminous efficiency and having an improved lifetime.

In order to achieve the above object, the present invention provides a compound represented by the following general formula (1).

In Formula 1,

A is a 6-membered aromatic ring or a 6-membered heteroaromatic ring,

B is a heteroaryl group having 5 to 60 nuclear atoms containing nitrogen,

X ₁ to X ₄ are the same or different and each independently N or C (R ₁ ), at least one of them being C (R ₁ )

R ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group If, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ or of, or may be to the adjacent groups combine to form a fused ring, wherein said R ₁ is a plurality, They are the same or different from each other,

Ar ₁ and Ar ₂ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ or, or a number, and to form the adjacent group fused ring ,

Alkyl group of the R _1, Ar ₁ and Ar _2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boronic A halogen atom, a cyano group, a nitro group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the aryl phosphine oxide group, and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylamine And when the substituent is plural, they may be the same or different from each other.

The present invention also provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by the general formula An electroluminescent device is provided. At least one of the organic compound layers including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer, A light-emitting layer, an electron transporting auxiliary layer, or an electron transporting layer. At this time, the compound represented by Formula 1 may be used as a phosphorescent host of the light emitting layer.

The compound represented by the general formula (1) of the present invention has excellent thermal stability and luminescent properties and can be used as a material of an organic material layer of an organic electroluminescent device.

Particularly, when the compound represented by the general formula (1) of the present invention is used as a phosphorescent host material or an electron transporting layer material, it is possible to provide an organic electroluminescent device having an organic electroluminescent device having an excellent electroluminescent performance, a low driving voltage, It is possible to manufacture a full-color display panel in which a light emitting element can be manufactured and its performance and lifetime are further improved.

Hereinafter, the present invention will be described in detail.

1. Organic compounds

)의 C2 위치에 전자 끌개기(EWG)가 연결된 구조를 기본 골격을 하며, 이러한 기본 골격에 다양한 치환기가 도입된 상기 화학식 1로 표시된다. The novel compounds according to the present invention can be prepared by reacting a pyrrolocarbazole moiety,

(EWG) is connected to the C2 position of the main skeleton, and the basic skeleton is represented by the above formula (1) in which various substituents are introduced.

As a conventional compound, a C2-C3 bond can be used as a high-efficiency material for a device without a substituent at the C2 and C3 positions (see the following compound I) of the pyrrolocarbazole moiety, There is a disadvantage in that the lifetime of the battery is deteriorated. In order to compensate for this, when the benzene is bonded to the C2 position (see the following compound II), the lifetime of the device is improved by 2 to 2.5 times, while the efficiency is reduced by 30 to 40%. The reason for this is that when an aryl group having an electro-donating property is substituted for a C2-C3 moiety having weak band binding in a pyrrolocarbazole moiety having a strong hole-accepting property, hole mobility ) Becomes stronger and the charge balance in the molecule can be broken. Therefore, in the present invention, in order to develop a novel compound having excellent properties compared to the above-mentioned conventional compounds, a compound having a durability of compound Thereby improving lifetime characteristics of the device and improving efficiency characteristics (see Evaluation Example 2, below).

Since the electron-donating group is bonded to the C2 position of the pyrrolocarbazole moiety having a weakly structurally weak bond, the compound represented by the formula (1) is excellent in thermal stability of the compound, and has excellent light-emitting performance, hole transport ability, great. Accordingly, when the compound represented by Formula 1 according to the present invention is applied to an organic electroluminescent device, the driving voltage, current efficiency, lifetime, etc. of the device can be improved. At this time, since the electron attracting group having a large electron absorbing property is bonded to the compound represented by the general formula (1), the entire molecule has bipolar characteristics, so that the bonding force between holes and electrons can be enhanced. The compound represented by the formula (1) can exhibit excellent luminescence characteristics and can be usefully used as a blue, green or red phosphorescent light emitting layer material of an organic electroluminescent device.

The compound represented by the general formula (1) has various substituents, especially an aryl group and / or a heteroaryl group, introduced into the basic skeleton, and the molecular weight of the compound is significantly increased, whereby the glass transition temperature can be improved. (E.g., 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')). In addition, the electron transporting ability can be improved according to the characteristics of the substituent bonded to the basic skeleton. Therefore, the compound represented by the formula (1) according to the present invention has electron mobility higher than a certain level and can be used as an electron transport layer material of an organic electroluminescent device.

On the other hand, in the phosphorescent light emitting layer of the organic electroluminescent device, the host material should have a triplet energy gap higher than the dopant of the host. That is, in order to effectively provide phosphorescent emission from the dopant, the lowest excitation state of the host must be higher energy than the lowest emission state of the dopant. The compound represented by the formula (1) has a higher energy level than that of the dopant by introducing a specific substituent group into a condensed indole derivative (pyrrolocarbazole moiety) having a broad singlet energy level and a high triplet energy level And can be used as a host material.

Furthermore, the compound represented by the above formula (1) is also effective in inhibiting crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound represented by the formula (1) according to the present invention can greatly improve performance and lifetime characteristics, thereby maximizing the performance of the full color organic light emitting panel.

As described above, the compound represented by Formula 1 can improve the phosphorescence characteristics of the organic electroluminescent device and improve the electron injecting / transporting ability, luminous efficiency, driving voltage and lifetime characteristics. Therefore, the compound of the formula (1) according to the present invention is preferably used as an organic layer material of an organic electroluminescence device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transporting layer material and an electron transporting layer material Can be used as a phosphorescent light-emitting layer material.

That is, when the compound of Chemical Formula 1 according to the present invention is used as an electron injecting / transporting layer material of an organic electroluminescent device or a blue, green and / or red phosphorescent host material, The efficiency and lifetime of the electroluminescent device can be greatly improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

Specifically, in the compound represented by the formula (1) according to the present invention, 'one electron-attracting group (EWG, B)' is connected to the terminal five-member ring of the 'pyrrolocarbazole moiety', and the pyrrolocarbazole moiety It is a structure in which various substituents are bonded to the five-membered rings in the thiazoles.

In the compound represented by the general formula (1), A is a 6-membered aromatic ring or a 6-membered heteroaromatic ring and forms a pyrrolocarbazole moiety.

Preferably, A is a 6-membered aromatic ring.

At this time, the structure of the pyrrolocarbazole moiety may be different depending on the bonding position of the six-membered aromatic ring. The compound represented by the formula (1) may be a compound represented by any one of the following formulas (2) to (7).

In Formulas 2 to 7, B, X ₁ to X ₄ , Ar ₁ and Ar ₂ are as defined in Formula 1, respectively.

In the compound represented by Formula 1, X ₁ to X ₄ are the same or different from each other and each independently N or C (R ₁ ), and at least one of them is C (R ₁ ).

Preferably, X ₁ to X ₄ may all be C (R ₁ ).

Wherein R ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cyclo An alkyl group having 3 to 40 nuclear atoms, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryl oxy group, C ₁ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic in, aryl of C ₆ ~ C ₆₀ phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of or, or may form a condensed ring with an adjacent group and coupling, in which the R ₁ a plurality They are the same or different.

Preferably, the plurality of R ₁ is hydrogen or a C ₁ to C ₄₀ alkyl group, or one R ₁ and another R ₁ may bond to each other to form a condensed aromatic ring.

Ar ₁ and Ar ₂ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~, or selected from the group consisting of an aryl amine of the C ₆₀ in, or may form a contiguous group fused ring .

Preferably, Ar ₁ and Ar ₂ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ ~ C ₆₀ aryloxy group, C ₆ ~ C ₆₀ aryl silyl group, C ₆ ~ C of the group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and And C ₆ to C ₆₀ arylamine groups.

In the compound of formula (1), B in which the electron-withdrawing group is located may be a heteroaryl group having 5 to 60 nucleus atoms containing nitrogen, which has a large electron-attracting property. Such a heteroaryl group may contain only nitrogen (N) as a hetero atom, or may further contain O or S together with N. [

Preferably, B may be a substituent represented by the following general formula (8).

In the formula (8), * represents a moiety bonded to the formula (1).

Y ₁ to Y ₅ are the same or different from each other, and each independently N or C (R ₂ ), and at least one of them is N.

Preferably, two or more of Y ₁ to Y ₅ may be N, and the remainder may be C (R ₂ ).

At this time, if the R ₂ is in plurality, they are the same or different, each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkenyl group of the C ₄₀ alkyl group, C ₂ ~ C ₄₀ of, C an alkynyl group of _{2 ~ C 40, C 3 ~} C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, the C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, a group C ₆ ~ C ₆₀ aryl silyl, C ₁ ~ group alkylboronic of C _40, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C aryl phosphine oxide ₆₀ group and a C ₆ ~, or selected from the group consisting of an aryl amine of the C _60, or adjacent groups fused ring Can be formed. In particular, one R ₂ and the other R ₂ may be bonded to each other to form a condensed ring.

Alkyl group of the R _2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkylox A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of aryl amine group of the C ₆₀ And when the substituent is plural, they may be the same or different.

The substituent represented by the formula (8) may be represented by any one of the substituents represented by the following formulas (A1) to (A15).

In the formulas (A1) to (A15), R ₂ is the same as defined in the above formula (8).

m is an integer of 0 to 4; When m is 0, it means that hydrogen is not substituted with R ₃ , and when m is an integer from 1 to 4, it means that at least one hydrogen is substituted with R ₃ . When R ₃ is plural, they may be the same or different and each independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ A cycloalkyl group having ₃ to ₄₀ carbon atoms, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ An alkyloxyl group, a C ₆ to C ₆₀ aryloxy group, a C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ or, or may form an adjacent group and a condensed ring have. At this time, one R ₃ and the other R R ₃ or one R ₃ and one R ₂ may be bonded to each other to form a condensed ring.

Alkyl group of the R _3, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkylox A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of aryl amine group of the C ₆₀ And when the substituent is plural, they may be the same or different.

Preferably, each R ₃ is independently selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or one R ₃ and the other R ₃ or one R ₃ and one R ₂ may be bonded to each other to form a condensed ring.

According to one embodiment of the present invention, the compound represented by Formula 1 may be prepared as a final compound from the following Synthesis Formula 2 or 3 after the intermediate (C2-PC) is prepared through Synthesis Formula 1 below.

[Synthesis formula 1]

[Synthesis formula 2]

[Synthesis formula 3]

In Formulas 1 to 3, A and B, X ₁ to X ₄ , Ar ₁ and Ar ₂ are as defined in Formula 1, and X is any one of Group 17 elements of the periodic table.

The compound represented by the formula (1) according to the present invention may be represented by the following compounds A-1 to A-8, B-1 to B-8, C-1 to C-8, D- The compound represented by any one of E-1 to E-8, F-1 to F-8, and G-1 to G-8. However, the compounds represented by formula (1) of the present invention are not limited by the following examples.

In the present invention, " alkyl " means a monovalent substituent derived from a straight or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

&Quot; Alkenyl " in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

The term " alkynyl " in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples of such alkynyls include, but are not limited to, ethynyl, 2-propynyl, and the like.

&Quot; Cycloalkyl " in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

&Quot; Heterocycloalkyl " in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon of the ring, preferably 1 to 3 carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

&Quot; Aryl " in the present invention means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

&Quot; Heteroaryl " in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, " alkyloxy " means a monovalent substituent group represented by R'O-, and R 'means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include linear, branched or cyclic structures. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

In the present invention, " aryloxy " means a monovalent substituent represented by RO-, and R means aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

&Quot; Alkylsilyl " in the present invention refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and " arylsilyl " means silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "alkyl boron" is boron substituted with alkyl having 1 to 40 carbon atoms, and "aryl boron" means boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms, and "arylphosphine oxide group" means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O do.

In the present invention, the term "condensed rings" means condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

&Quot; Arylamine " in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

The compound represented by formula (1) of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.

2. Organic Field  Light emitting element

The present invention provides an organic electroluminescent device comprising a compound represented by the above formula (1).

More specifically, the organic electroluminescent device according to the present invention includes at least one anode, an anode, and at least one organic layer sandwiched between the anode and the cathode, and at least one of the one or more organic layers Include the compounds represented by the above formula (1). At this time, the compounds may be used alone or in combination of two or more.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer. ≪ / RTI > compounds. Specifically, the organic compound layer containing the compound of Formula 1 is preferably a light emitting layer, an electron transporting auxiliary layer, or an electron transporting layer.

The light emitting layer of the organic electroluminescence device of the present invention may include a host material (preferably, a phosphorescent host material). The light emitting layer of the organic electroluminescent device of the present invention may contain a compound other than the compound of Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, and examples thereof include a substrate, an anode, a hole injecting layer, a hole transporting layer, a luminescent auxiliary layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode sequentially laminated Structure. Further, an electron transporting auxiliary layer may be disposed between the light emitting layer and the electron transporting layer. At least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting supporting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, The transporting auxiliary layer or the electron transporting layer may contain the compound represented by the above formula (1). Here, the structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

Meanwhile, the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula have.

The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate used in the fabrication of the organic electroluminescent device of the present invention is not particularly limited, but silicon wafer, quartz, glass plate, metal plate, plastic film and sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO2: Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; And multi-layer structure materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

The hole injecting layer, the hole transporting layer, and the light emitting auxiliary layer are not particularly limited, and ordinary materials known in the art can be used.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[ Preparation Example  1] C2-PC- 1 of  synthesis

≪ Step 1 > 5- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1H- indole  synthesis

(100.0 g, 510.1 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3 Dioxaborolane (142.5 g, 561.1 mmol), Pd (dppf) Cl ₂ (44.7 g, 51.0 mmol), KOAc (144.1 g, 1.52 mol) and 1,4- Lt; / RTI >

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 8: 1 (v / v)) to obtain 5- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -1H-indole (93.0 g, yield 75%).

^{1 H-NMR: δ 1.24 (} s, 12H), 6.50 (d, 1H), 7.30 (d, 1H), 7.51 (d, 1H), 7.63 (d, 1H), 7.98 (s, 1H), 10.1 ( b, 1H)

<Step 2> Synthesis of 5- (2- nitrophenyl ) -1H- indole  Synthesis of

-1H-indole (93.0 g, 382.6 mmol), 1-bromo-2-nitrobenzene (92.7 g, , 459.1 mmol), Pd (PPh 3) 4 (22.1 g, 19.1 mmol), K 2 CO 3 (105.8 g, 765.2 mmol), 1000 ml of 1,4-dioxane and 200 ml of H ₂ O were mixed and stirred at 120 ° C for 4 hours.

After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (hexane: EA = 6: 1 (v / v)) to obtain 5- (2-nitrophenyl) -1H-indole (73.8 g, yield 81%).

^{1 H-NMR: δ 6.45 (} d, 1H), 7.27 (d, 1H), 7.67-7.77 (m, 3H), 7.87-8.05 (m, 4H), 10.1 (b, 1H)

&Lt; Step 3 > 5- (2- nitrophenyl ) -1-phenyl-1H- indole  Synthesis of

Iodobenzene (75.9 g, 371.9 mmol), Cu (9.8 g, 154.9 mmol), K ₂ CO ₃ (85.7 g, 619.8 mmol) were added to a solution of 5- (2-nitrophenyl) ) And 1500 ml of Nitrobenzene were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and the residue was purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to give 5- (2-nitrophenyl) 1H-indole (66.2 g, yield 68%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.50-7.72 (m, 7H), 7.88-7.89 (m, 2H), 8.00-8.03 (m, 2H), 8.13 (d, 1H), 8.30 (d , 1H)

<Step 4> Synthesis of 3-phenyl-3,10- dihydropyrrolo [3,2-a] carbazole  Synthesis of

1000 mL of 1,2-dichlorobenzene (138.2 g, 526.8 mmol) and triphenylphosphine (PPh ₃ ) (66.2 g, 210.7 mmol) were added to a solution of 12 Lt; / RTI &gt;

After completion of the reaction, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and the residue was purified by column chromatography (Hexane: MC = 8: 1 (v / v)) to obtain 25.0 g of 3-phenyl-3,10- dihydropyrrolo [3,2- %).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.20 (dd, 1H), 7.50-7.62 (m, 8H), 7.94-7.96 (m, 2H), 8.19 (d, 1H), 8.53 (b, 1H )

&Lt; Step 5 > C2-PC- 1 of  synthesis

(25.0 g, 88.5 mmol), 2-chloro-3-phenylquinoxaline (23.4 g, 97.3 mmol) and aluminum chloride (AlCl ₃ ) 13.0 g, 97.3 mmol) and 1,2-dichloroethane (ο-DCE) (500 ml) were added thereto, followed by stirring for 12 hours.

After completion of the reaction, 1,2-dichloroethane was removed, and the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain C2-PC-1 (27.6 g, yield 64%).

^{1 H-NMR: δ 6.80 (} s, 1H), 7.20 (dd, 1H), 7.32 (dd, 2H), 7.50-7.67 (m, 10H), 7.79-7.80 (m, 2H), 8.03 (d, 2H ), 8.19 (d, IH), 8.62 (b, IH)

[ Preparation Example  2] C2-PC- 2 of  synthesis

The procedure of Preparation Example 1 was repeated except that 2-chloro-4-phenylquinazoline (23.4 g, 97.3 mmol) was used instead of 2-chloro-3-phenylquinoxaline in Step 5, 2 (31.0 g, yield 72%).

^{1 H-NMR: δ 6.80 (} s, 1H), 7.20 (dd, 1H), 7.49-7.65 (m, 11H), 7.80-7.84 (m, 4H), 7.94-7.96 (m, 2H), 8.13-8.19 (m, 2 H), 8.58 (b, 1 H)

[ Preparation Example  3] C2-PC- 3 of  synthesis

The procedure of Preparation Example 1 was repeated except that 2-chloro-4,6-diphenylpyrimidine (26.0 g, 97.3 mmol) was used instead of 2-chloro-3-phenylquinoxaline in Step 5, PC-3 (23.6 g, yield 52%) was obtained.

^{1 H-NMR: δ 6.80 (} s, 1H), 7.20 (dd, 1H), 7.49-7.63 (m, 13H), 7.94-7.96 (m, 6H), 8.19 (d, 1H), 8.58 (b, 1H ), 8.73 (s, 1 H)

[ Preparation Example  4] C2-PC- 4 of  synthesis

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (26.1 g, 97.3 mmol) was used in place of 2-chloro-3-phenylquinoxaline in Step 5 To obtain the target compound C2-PC-4 (28.6 g, yield 63%).

^{1 H-NMR: δ 6.80 (} s, 1H), 7.20 (dd, 1H), 7.50-7.63 (m, 13H), 7.94-7.96 (m, 2H), 8.19 (d, 1H), 8.36-8.38 (m , 4H), 8.58 (b, 1 H)

[ Preparation Example  5] C2-PC- 5 of  synthesis

Bromo-2-nitronaphthalene (115.7 g, 459.1 mmol) was used in place of 1-bromo-2-nitrobenzene in Step 2 and 2-chloro-4, C2-PC-5 (21.7 g, yield 48%) was obtained in the same manner as in Preparation Example 1, except that 6-diphenyl-1,3,5-triazine (26.1 g, .

^{1 H-NMR: δ 6.80 (} s, 1H), 7.50-7.65 (m, 15H), 7.94-7.99 (m, 3H), 8.37-8.40 (m, 4H), 8.54 (d, 1H), 8.71 (b , 1H)

[ Preparation Example  6] C2-PC- 6 of  synthesis

<Step 1> Synthesis of 4- (4,4,5,5- tetramethyl -1,3,2- dioxaborolan -2- yl ) -1H- indole  Synthesis of

(100.0 g, 510.1 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3 Dioxaborolane (142.5 g, 561.1 mmol), Pd (dppf) Cl ₂ (44.7 g, 51.0 mmol), KOAc (144.1 g, 1.52 mol) and 1,4- Lt; / RTI &gt;

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO ₄ and purified by column chromatography (Hexane: EA = 8: 1 (v / v)) to obtain 4- (4,4,5,5-tetramethyl -1,3,2-dioxaborolan-2-yl) -1H-indole (104.2 g, yield 84%).

^{1 H-NMR: δ 1.20 (} s, 12H), 6.56 (d, 1H), 7.14 (d, 1H), 7.37-7.42 (m, 2H), 7.63 (d, 1H), 8.34 (b, 1H)

<Step 2> Synthesis of 4- (2- nitrophenyl ) -1H- indole  Synthesis of

-1H-indole (104.2 g, 428.4 mmol), 1-bromo-2-nitrobenzene (103.9 g, , 514.2 mmol), Pd (PPh 3) 4 (24.8 g, 21.4 mmol), K 2 CO 3 (118.4 g, 856.9 mmol), 1000 ml of 1,4-dioxane and 200 ml of H ₂ O were mixed and stirred at 120 ° C for 4 hours.

After the reaction was completed, the reaction mixture was extracted with methylene chloride, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (Hexane: EA = 6: 1 (v / v)) to obtain 4- (2-nitrophenyl) -1H-indole (86.8 g, yield 85%).

^{1 H-NMR: δ 6.56 (} d, 1H), 7.14 (d, 1H), 7.56 (dd, 1H), 7.72-7.73 (m, 2H), 7.89-8.03 (m, 4H), 8.32 (b, 1H )

<Step 3> Synthesis of 4- (2- nitrophenyl ) -1-phenyl-1H- indole  Synthesis of

(86.8 g, 364.2 mmol), Iodobenzene (89.2 g, 437.0 mmol), Cu (11.6 g, 182.1 mmol), K ₂ CO ₃ (100.7 g, 728.4 mmol) were added under a nitrogen stream. ) And 1500 ml of Nitrobenzene were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, the water was removed with MgSO _4, and the residue was purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to give 4- (2-nitrophenyl) 1H-indole (64.1 g, yield 56%).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.50-7.72 (m, 8H), 7.89 (dd, 1H), 8.00-8.04 (m, 3H), 8.22 (d, 1H)

<Step 4> Synthesis of 3-phenyl-3,6- dihydropyrrolo [2,3-c] carbazole  Synthesis of

(64.1 g, 204.0 mmol), triphenylphosphine (133.7 g, 509.9 mmol) and 1,2-dichlorobenzene (1000 ml) were added under nitrogen atmosphere and stirred for 12 hours.

After completion of the reaction, 1,2-dichlorobenzene was removed, and the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 8: 1 (v / v)) to obtain 41.5 g of 3-phenyl-3,6- dihydropyrrolo [2,3- %).

^{1 H-NMR: δ 6.52 (} d, 1H), 7.20 (dd, 1H), 7.50-7.63 (m, 9H), 7.94 (d, 1H), 8.19 (d, 1H), 8.57 (b, 1H)

&Lt; Step 5 > C2-PC- 6 of  synthesis

(41.5 g, 146.8 mmol), 2-chloro-4-phenylquinazoline (38.9 g, 161.5 mmol) and aluminum chloride (21.5 g, 161.5 mmol) in a stream of nitrogen mmol) and 1,2-dichloroethane (500 ml) were added thereto, followed by stirring for 12 hours.

After completion of the reaction, 1,2-dichloroethane was removed, and the mixture was extracted with dichloromethane, added with MgSO ₄ and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain C2-PC-6 (43.6 g, yield 61%).

^{1 H-NMR: δ 6.80 (} s, 1H), 7.20 (dd, 1H), 7.49-7.65 (m, 12H), 7.80-7.84 (m, 4H), 7.94 (d, 1H), 8.13-8.19 (m , 2H), 8.59 (b, 1 H)

[ Preparation Example  7] C2-PC- 7's  synthesis

Except that 2-chloro-4,6-diphenyl-1,3,5-triazine (43.2 g, 161.5 mmol) was used instead of 2-chloro-4-phenylquinazoline in Step 5 To obtain a target compound C2-PC-7 (43.7 g, yield 58%).

^{1 H-NMR: δ 6.80 (} s, 1H), 7.20 (dd, 1H), 7.50 -7.63 (m, 14H), 7.94 (d, 1H), 8.19 (d, 1H), 8.36-8.37 (m, 4H ), 8.63 (b, IH)

[ Synthetic example  1] Synthesis of B-1

(3.3 g, 6.7 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine g, 8.0 mmol), NaH (0.16 g, 6.7 mmol) and DMF (25 ml) were mixed and stirred at room temperature for 1 hour. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain the target compound B-1 (4.0 g, yield 76%).

Mass (theory: 793.93, measurement: 793 g / mol)

[ Synthetic example  2] Synthesis of B-2

(Dibenzo [b, d] furan-4-yl) -4-chloro-6- (3.8 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the title compound B-2 was used instead of 2- ).

Mass (theory: 807.92, measurement: 807 g / mol)

[ Synthetic example  3] Synthesis of B-3

2-chloro-4- (dibenzo [b, d] furan-3-yl) -4-chloro-6- 3 (3.9 g, yield 72%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that 1-benzyl-6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) ).

Mass (theory: 807.92, measurement: 807 g / mol)

[ Synthetic example  4] Synthesis of B-4

(3.3 g, 6.7 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Pd (OAc) ₂ (0.15 g, 0.67 mmol), P- ( t- Bu) ₃ (0.33 ml, 1.34 mmol), NaO t- Bu (1.3 g, 13.4 mmol) and 25 ml of xylene were mixed and stirred at 140 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound B-4 (4.1 g, yield 70%).

Mass (theory: 870.03, measurement: 870 g / mol)

[ Synthetic example  5] Synthesis of B-5

2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- (3.4 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the starting material (2.1 g, 8.0 mmol) was used.

Mass (theory: 717.84, measured: 717 g / mol)

[ Synthetic example  6] Synthesis of B-6

2-chlorothiochromeno [4,3,2-de] quinazoline (prepared in Example 1) instead of 2- (3'-chloro- [1,1'- biphenyl] 2.2 g, 8.0 mmol), the target compound B-6 (3.5 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 4.

Mass (theory: 720.85, measured: 720 g / mol)

[ Synthetic example  7] Synthesis of B-7

2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2- (3'-chloro- [1,1'- biphenyl] -3-yl) -4,6-diphenyl- , The target compound B-7 (3.5 g, yield 75%) was obtained by carrying out the same procedure as in Synthesis Example 4.

Mass (theory: 690.81, measurement: 690 g / mol)

[ Synthetic example  8] Synthesis of B-8

2-chloro-4-phenylbenzo [4,5] thieno [2,3-d] pyrimidine instead of 2- (3'-chloro- [1,1'- (3.6 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 4, except that 3-benzyloxy-3,2-d] pyrimidine (2.4 g, 8.0 mmol) was used.

Mass (theory: 746.89, found: 746 g / mol)

[ Synthetic example  9] Synthesis of A-1

(3.5 g, yield 65%) was obtained in the same manner as in Synthesis Example 1, except that C2-PC-1 was used instead of C2-PC-2.

Mass (theory: 793.93, measurement: 793 g / mol)

[ Synthetic example  10] Synthesis of A-2

C2-PC-2 was used instead of C2-PC-2, and 2- (2- ((1,1'-biphenyl) The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) To obtain the target compound A-2 (3.3 g, yield 62%).

Mass (theory: 807.92, measurement: 807 g / mol)

[ Synthetic example  11] Synthesis of A-3

C2-PC-2 was used instead of C2-PC-2, and 2- (2- ((1,1'-biphenyl) The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) To obtain the target compound A-3 (3.6 g, yield 67%).

Mass (theory: 807.92, measurement: 807 g / mol)

[ Synthetic example  12] Synthesis of A-4

The procedure of Synthetic Example 4 was repeated except that C2-PC-1 was used instead of C2-PC-2 to obtain the desired compound A-4 (4.1 g, yield 71%).

Mass (theory: 870.03, measurement: 870 g / mol)

[ Synthetic example  13] Synthesis of A-5

C2-PC-2 was used instead of C2-PC-2, and 2- (2- ((1,1'-biphenyl) (2.5 g, yield 53%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) %).

Mass (theory: 717.84, measurement: 711 g / mol)

[ Synthetic example  14] Synthesis of A-6

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (3.3 g, yield 68%) was obtained in the same manner as in Synthesis Example 4, except that 2-chlorothiochromeno [4,3,2-de] quinazoline (2.2 g, 8.0 mmol) ).

Mass (theory: 720.85, measured: 720 g / mol)

[ Synthetic example  15] Synthesis of A-7

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine (3.2 g, yield 69%) was obtained in the same manner as in Synthesis Example 4, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol)

Mass (theory: 690.81, measurement: 690 g / mol)

[ Synthetic example  16] Synthesis of A-8

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Synthetic Example 4 was repeated except that 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine (2.4 g, 8.0 mmol) 8 (3.1 g, yield 62%).

Mass (theory: 746.89, found: 746 g / mol)

[ Synthetic example  17] Synthesis of C-1

C-1 (3.9 g, yield 71%) was obtained in the same manner as in Synthesis Example 1, except that C2-PC-3 was used in place of C2-PC-2.

Mass (theory: 819.55, measurement: 819 g / mol)

[ Synthetic example  18] Synthesis of C-2

C2-PC-3 was used in place of C2-PC-2, and 2- (2- [(1,1'-biphenyl) The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) To obtain the target compound C-2 (3.6 g, yield 64%).

Mass (theory: 833.54, measurement: 833 g / mol)

[ Synthetic example  19] Synthesis of C-3

C2-PC-3 was used instead of C2-PC-2, 2-chloro-4- (dibenzo [b, d] furan-3-yl) -4-chloro-6- 3 (3.7 g, yield 66%) was obtained by carrying out the same processes as in Synthesis Example 1, except that the starting material C-3 was used instead of 2- ).

Mass (theory: 833.54, measurement: 833 g / mol)

[ Synthetic example  20] Synthesis of C-4

C-4 (3.7 g, yield 61%) was obtained by carrying out the same procedure as in Synthesis Example 4, except that C2-PC-3 was used instead of C2-PC-2.

Mass (theory value: 895.65, measurement value: 895 g / mol)

[ Synthetic example  21] Synthesis of C-5

C2-PC-3 was used in place of C2-PC-2, and 2- (2- [(1,1'-biphenyl) (3.4 g, yield 69%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) %).

Mass (theory: 743.46, found: 743 g / mol)

[ Synthetic example  22] Synthesis of C-6

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine 6 (3.7 g, yield 73%) was obtained by following the same procedure as in Synthesis Example 4, except that 2-chlorothiochromeno [4,3,2-de] quinazoline (2.2 g, 8.0 mmol) ).

Mass (theory: 746.47, found: 746 g / mol)

[ Synthetic example  23] Synthesis of C-7

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine C-7 (3.6 g, yield 74%) was obtained in the same manner as in Synthesis Example 4, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-chloro-4-

Mass (theory: 716.43, measurement: 716 g / mol)

[ Synthetic example  24] Synthesis of C-8

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Synthetic Example 4 was repeated except that 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine (2.4 g, 8.0 mmol) 8 (4.0 g, yield 78%).

Mass (theory: 772.51, measurement: 772 g / mol)

[ Synthetic example  25] Synthesis of D-1

D-1 (3.7 g, yield 68%) was obtained in the same manner as in Synthesis Example 1, except that C2-PC-4 was used in place of C2-PC-2.

Mass (theory: 820.95, measured: 820 g / mol)

[ Synthetic example  26] Synthesis of D-2

4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2 - ([1,1'-biphenyl] The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) To obtain the target compound D-2 (3.7 g, yield 67%).

Mass (theory: 834.94, measurement: 834 g / mol)

[ Synthetic example  27] Synthesis of D-3

C2-PC-4 was used instead of C2-PC-2, 2-chloro-4- (dibenzo [b, d] furan-3-yl) -4-chloroquinoline in place of 2 - ([1,1'- D-3 (3.9 g, yield 69%) was obtained by carrying out the same procedure as in Synthesis Example 1, except for using 2- ).

Mass (theory: 834.94, measurement: 834 g / mol)

[ Synthetic example  28] Synthesis of D-4

D-4 (3.5 g, yield 59%) was obtained in the same manner as in Synthesis Example 4, except that C2-PC-4 was used in place of C2-PC-2.

Mass (theory: 897.05, measurement: 897 g / mol)

[ Synthetic example  29] Synthesis of D-5

4-yl) -4-chloro-6-phenyl-1,3,5-triazine instead of 2 - ([1,1'-biphenyl] D-5 (3.6 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) %).

Mass (theory: 744.86, found: 744 g / mol)

[ Synthetic example  30] Synthesis of D-6

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine D-6 (3.6 g, yield 72%) was obtained in the same manner as in Synthesis Example 4, except that 2-chlorothiochromeno [4,3,2-de] quinazoline (2.2 g, 8.0 mmol) ).

Mass (theory: 747.87, found: 747 g / mol)

[ Synthetic example  31] Synthesis of D-7

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine D-7 (3.4 g, yield 70%) was obtained in the same manner as in Synthesis Example 4, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-chloro-4-

Mass (theory: 717.83, measurement: 717 g / mol)

[ Synthetic example  32] Synthesis of D-8

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Synthesis Example 4 was repeated except that 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine (2.4 g, 8.0 mmol) 8 (3.7 g, yield 72%).

Mass (theory: 773.91, measurement: 773 g / mol)

[ Synthetic example  33] Synthesis of E-1

(3.8 g, 6.7 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine g, 8.0 mmol), NaH (0.16 g, 6.7 mmol) and DMF (25 ml) were mixed and stirred at room temperature for 1 hour. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain the target compound E-1 (3.6 g, yield 62%).

Mass (theory: 871.01, measurement: 871 g / mol)

[ Synthetic example  34] Synthesis of E-2

(Dibenzo [b, d] furan-4-yl) -4-chloro-6- E-2 (3.3 g, yield 55%) was obtained by carrying out the same procedure as in Synthesis Example 33, except for using 2- ).

Mass (theory: 885.00, measurement: 885 g / mol)

[ Synthetic example  35] Synthesis of E-3

2-chloro-4- (dibenzo [b, d] furan-3-yl) -4-chloro-6- 3 (3.7 g, yield 63%) was obtained by carrying out the same procedure as in Synthesis Example 33, except that the starting material E-3 was used instead of 2- ).

Mass (theory: 885.00, measurement: 885 g / mol)

[ Synthetic example  36] Synthesis of E-4

(3.8 g, 6.7 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- Pd (OAc) ₂ (0.15 g, 0.67 mmol), P- ( t- Bu) ₃ (0.33 ml, 1.34 mmol), NaO t- Bu (1.3 g, 13.4 mmol) and 25 ml of xylene were mixed and stirred at 140 ° C for 3 hours. After completion of the reaction, the solid salt was filtered and then purified by column chromatography to obtain the target compound E-4 (4.2 g, yield 66%).

Mass (theory: 947.11, measurement: 947 g / mol)

[ Synthetic example  37] Synthesis of E-5

2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- E-5 (2.8 g, yield 52%) was obtained by carrying out the same procedure as in Synthesis Example 33, except that the title compound (2.1 g, 8.0 mmol) was used.

Mass (theory: 794.92, found: 794 g / mol)

[ Synthetic example  38] Synthesis of E-6

2-chlorothiochromeno [4,3,2-de] quinazoline (prepared in Example 1) instead of 2- (3'-chloro- [1,1'- biphenyl] 2.2 g, 8.0 mmol), the target compound E-6 (3.8 g, yield 71%) was obtained.

Mass (theory: 797.93, found: 797 g / mol)

[ Synthetic example  39] Synthesis of E-7

2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2- (3'-chloro- [1,1'- biphenyl] -3-yl) -4,6-diphenyl- (3.8 g, yield 74%) was obtained by carrying out the same procedure as in Synthesis Example 36, except that E-7 (3.8 g, yield: 74%) was obtained.

Mass (theory: 767.89, measured: 767 g / mol)

[ Synthetic example  40] Synthesis of E-8

2-chloro-4-phenylbenzo [4,5] thieno [2,3-d] pyrimidine instead of 2- (3'-chloro- [1,1'- E-8 (4.0 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 36, except that 3-benzyloxy-3,2-d] pyrimidine (2.4 g, 8.0 mmol) was used.

Mass (theory: 823.97, measurement: 823 g / mol)

[ Synthetic example  41] Synthesis of F-1

The procedure of Synthesis Example 1 was repeated, except that C2-PC-6 was used instead of C2-PC-2 to obtain the desired compound F-1 (3.8 g, yield 71%).

Mass (theory: 793.93, measurement: 793 g / mol)

[ Synthetic example  42] Synthesis of F-2

C2-PC-6 was used in place of C2-PC-2, and 2- (2- ((1,1'-biphenyl) The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) To obtain the objective compound F-2 (4.0 g, yield 73%).

Mass (theory: 807.92, measurement: 807 g / mol)

[ Synthetic example  43] Synthesis of F-3

C2-PC-6 was used instead of C2-PC-2, 2-chloro-4- (dibenzo [b, d] furan-3-yl) -4-chloro-6- 3 (4.1 g, yield 75%) was obtained by following the same procedure as in Synthesis Example 1, except that the title compound was used instead of 2- ).

Mass (theory: 807.92, measurement: 807 g / mol)

[ Synthetic example  44] Synthesis of F-4

The procedure of Synthesis Example 4 was repeated except that C2-PC-6 was used instead of C2-PC-2 to obtain the desired compound F-4 (3.6 g, yield 61%).

Mass (theory: 870.03, measurement: 870 g / mol)

[ Synthetic example  45] Synthesis of F-5

C2-PC-6 was used in place of C2-PC-2, and 2- (2- ((1,1'-biphenyl) (3.5 g, yield 72%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) %).

Mass (theory: 717.84, measurement: 711 g / mol)

[ Synthetic example  46] Synthesis of F-6

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine 6 (3.6 g, yield 74%) was obtained in the same manner as in Synthesis Example 4, except that 2-chlorothiochromeno [4,3,2-de] quinazoline (2.2 g, 8.0 mmol) ).

Mass (theory: 720.85, measured: 720 g / mol)

[ Synthetic example  47] Synthesis of F-7

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine F-7 (3.6 g, yield 77%) was obtained in the same manner as in Synthesis Example 4, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-chloro-4-

Mass (theory: 690.81, measurement: 690 g / mol)

[ Synthetic example  48] Synthesis of F-8

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Synthesis Example 4 was repeated except that 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine (2.4 g, 8.0 mmol) 8 (3.8 g, yield 76%).

Mass (theory: 746.89, found: 746 g / mol)

[ Synthetic example  49] Synthesis of G-1

G-1 (3.5 g, yield 64%) was obtained in the same manner as in Synthesis Example 1, except that C2-PC-7 was used in place of C2-PC-2.

Mass (theory: 820.95, measured: 820 g / mol)

[ Synthetic example  50] Synthesis of G-2

C2-PC-7 was used in place of C2-PC-2, and 2- (2- ((1,1'-biphenyl) The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) To obtain the target compound G-2 (4.0 g, yield 72%).

Mass (theory: 834.94, measurement: 834 g / mol)

[ Synthetic example  51] Synthesis of G-3

C2-PC-7 was used in place of C2-PC-2, and 2- (2- ((1,1'-biphenyl) The same procedure as in Synthesis Example 1 was carried out except that dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) To obtain the target compound G-3 (4.1 g, yield 73%).

Mass (theory: 834.94, measurement: 834 g / mol)

[ Synthetic example  52] Synthesis of G-4

G-4 (3.8 g, yield 64%) was obtained by carrying out the same procedure as in Synthesis Example 4, except that C2-PC-7 was used instead of C2-PC-2.

Mass (theory: 897.05, measurement: 897 g / mol)

[ Synthetic example  53] Synthesis of G-5

C2-PC-7 was used in place of C2-PC-2, and 2- (2- ((1,1'-biphenyl) (3.3 g, yield 66%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that chloro-4,6-diphenyl-1,3,5-triazine (2.1 g, 8.0 mmol) %).

Mass (theory: 744.86, found: 744 g / mol)

[ Synthetic example  54] Synthesis of G-6

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine G-6 (3.1 g, yield 61%) was obtained in the same manner as in Synthesis Example 4, except that 2-chlorothiochromeno [4,3,2-de] quinazoline (2.2 g, 8.0 mmol) ).

Mass (theory: 747.87, found: 747 g / mol)

[ Synthetic example  55] Synthesis of G-7

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine G-7 (3.0 g, yield 63%) was obtained in the same manner as in Synthesis Example 4, except that 2-chloro-4-phenylquinazoline (1.9 g, 8.0 mmol) was used instead of 2-chloro-4-

Mass (theory: 717.83, measurement: 717 g / mol)

[ Synthetic example  56] Synthesis of G-8

(3'-chloro- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Synthetic Example 4 was repeated except that 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine (2.4 g, 8.0 mmol) 8 (3.5 g, yield 67%).

Mass (theory: 773.91, measurement: 773 g / mol)

[ Example  1 to 35] green organic Field  Fabrication of light emitting device

The compounds A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D-5, E-1 to E- To F-5, and G-1 to G-5 were subjected to high purity sublimation purification by a conventionally known method, and a green organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

On the thus prepared ITO transparent electrode, each compound A-1 to A-5, B-1 to B-5, C-1 to C-5, and D- Ir (ppy) ₃ (300 nm) / BCP (10 nm) / ₂ of Ir-1 to D-5, E-1 to E-5, F-1 to F-5, G- Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  1] Green organic Field  Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 1, except that CBP was used instead of Compound A-1 as a host material in forming the light emitting layer.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP, Alq ₃ and BCP used in Examples 1 to 35 and Comparative Example 1 are as follows.

[ Evaluation example  One]

The driving voltage, current efficiency and emission peak at each current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices fabricated in Examples 1 to 35 and Comparative Example 1, and the results are shown in Table 1 below .

Sample Host Driving voltage
(V) Emission peak
(nm) Current efficiency
(cd / A) Example 1 A-1 6.77 517 41.3 Example 2 A-2 6.7 515 41.2 Example 3 A-3 6.51 518 41.2 Example 4 A-4 6.77 518 38.9 Example 5 A-5 6.7 515 41.3 Example 6 B-1 6.51 515 41.2 Example 7 B-2 6.77 518 41.3 Example 8 B-3 6.7 515 41.3 Example 9 B-4 6.77 515 41.2 Example 10 B-5 6.7 515 38.9 Example 11 C-1 6.51 518 41.3 Example 12 C-2 6.77 518 41.3 Example 13 C-3 6.7 515 41.2 Example 14 C-4 6.51 515 38.9 Example 15 C-5 6.77 518 41.3 Example 16 D-1 6.7 515 41.3 Example 17 D-2 6.66 518 41.3 Example 18 D-3 6.81 517 41.2 Example 19 D-4 6.68 518 41.2 Example 20 D-5 6.66 518 38.9 Example 21 E-1 6.7 518 41.3 Example 22 E-2 6.7 517 41.3 Example 23 E-3 6.77 518 41.3 Example 24 E-4 6.7 518 41.2 Example 25 E-5 6.51 515 41.3 Example 26 F-1 6.77 515 41.3 Example 27 F-2 6.7 518 41.2 Example 28 F-3 6.51 515 38.9 Example 29 F-4 6.77 515 41.3 Example 30 F-5 6.7 515 42.0 Example 31 G-1 6.66 515 41.3 Example 32 G-2 6.81 515 41.2 Example 33 G-3 6.68 518 41.2 Example 34 G-4 6.5 515 38.9 Example 35 G-5 6.6 515 41.3 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, the compounds A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D- Green organic electroluminescent devices (Examples 1 to 35) using E-5, F-1 to F-5 and G-1 to G-5 as light emitting layer hosts (Comparative Example 1), the current efficiency and the driving voltage were superior.

[ Example  36 to 56] Red organic Field  Fabrication of light emitting device

The compounds A-6 to A-8, B-6 to B-8, C-6 to C-8, D-6 to D-8, E-6 to E- To F-8, and G-6 to G-8 were subjected to high-purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was fabricated according to the following procedure.

First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

On the ITO transparent electrode thus prepared, the respective compounds A-6 to A-8, B-6 to B-8, C-6 to C-8 and D-90 of m-MTDATA (60 nm) / TCTA (Piq) ₂ Ir (acac) (300 nm) / BCP (10 nm) at a concentration of 10-6%, D-8, E-6 to E-8, F-6 to F- nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  2]

A red organic electroluminescent device was fabricated in the same manner as in Example 36 except that CBP was used in place of Compound A-6 as a host material in forming the light emitting layer.

[ Comparative Example  3]

A red organic electroluminescent device was fabricated in the same manner as in Example 36 except that Compound I was used instead of Compound A-6 as a host material in forming the light emitting layer.

[ Comparative Example  4]

A red organic electroluminescent device was fabricated in the same manner as in Example 36 except that Compound II was used instead of Compound A-6 as a host material in forming the light emitting layer.

The structures of (piq) ₂ Ir (acac), Compound I and Compound II used in Examples 36 to 56 and Comparative Examples 2 to 4 are as follows.

[ Evaluation example  2]

The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for each red organic electroluminescent device fabricated in Examples 36 to 56 and Comparative Examples 2 to 4. The results are shown in Table 2 below.

Sample Host Driving voltage
(V) Current efficiency
(cd / A) Example 36 A-6 4.62 15.2 Example 37 A-7 4.63 13.4 Example 38 A-8 4.81 10.8 Example 39 B-6 4.63 13.2 Example 40 B-7 4.81 11.5 Example 41 B-8 4.81 12.3 Example 42 C-6 4.64 11.9 Example 43 C-7 4.64 12.5 Example 44 C-8 4.53 11.5 Example 45 D-6 4.55 12.3 Example 46 D-7 4.64 11.9 Example 47 D-8 4.87 12.5 Example 48 E-6 4.54 13.2 Example 49 E-7 4.81 11.5 Example 50 E-8 4.81 12.3 Example 51 F-6 4.64 11.9 Example 52 F-7 4.55 12.5 Example 53 F-8 4.64 11.5 Example 54 G-6 4.87 12.5 Example 55 G-7 4.54 13.2 Example 56 G-8 4.81 11.5 Comparative Example 2 CBP 5.25 8.2 Comparative Example 3 Compound I 5.01 10.5 Comparative Example 4 Compound II 5.52 6.8

As shown in Table 2, the compounds A-6 to A-8, B-6 to B-8, C-6 to C-8, D-6 to D- Red organic electroluminescent devices (Examples 36 to 56) using organic electroluminescent compounds E-8, F-6 to F-8, and G-6 to G- It was found that the current efficiency and the driving voltage were superior to those of the red organic electroluminescent devices (Comparative Examples 2 to 4) used.

[ Example  57 to 91] Blue organic Field  Fabrication of light emitting device

The compounds A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D-5, E-1 to E- To F-5 and G-1 to G-5 were subjected to high purity sublimation purification by a conventionally known method, and blue organic electroluminescent devices were prepared as follows.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode thus prepared, a mixture of DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / 95% AND + 5% DS-405 1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D- 1 to G-5 (5 nm) / Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  5] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 57 except that the electron transporting layer material was not included and the electron transport layer material Alq ₃ was deposited at 30 nm instead of 25 nm.

[ Comparative Example  6] blue organic Field  Fabrication of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Example 57 except that BCP was used as the electron transporting auxiliary layer material instead of the compound A-1 as the electron transporting auxiliary layer material.

The structure of the AND used in Examples 57 to 91 and Comparative Examples 5 and 6 is as follows.

[ Evaluation example  3]

The driving voltage, current efficiency, emission peak and lifetime (T ₉₇ ) at current densities of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices fabricated in Examples 57 to 91 and Comparative Examples 5 and 6, The results are shown in Table 3 below.

Sample Electron transporting auxiliary layer Driving voltage
(V) Current efficiency
(cd / A) Emission peak
(nm) life span
(hr, T ₉₇ ) Example 57 A-1 4.3 6.0 459 37 Example 58 A-2 5.3 6.0 459 39 Example 59 A-3 5.3 5.9 459 44 Example 60 A-4 5.1 6.3 459 43 Example 61 A-5 5.2 5.9 459 48 Example 62 B-1 5.2 6.2 459 38 Example 63 B-2 4.3 6.1 459 37 Example 64 B-3 4.3 6.0 459 39 Example 65 B-4 5.3 5.9 451 44 Example 66 B-5 5.1 6.3 459 43 Example 67 C-1 5.3 5.9 459 48 Example 68 C-2 5.2 6.2 459 49 Example 69 C-3 5.0 6.1 459 41 Example 70 C-4 4.8 6.1 462 39 Example 71 C-5 5.1 6.0 463 44 Example 72 D-1 5.0 6.0 460 43 Example 73 D-2 4.8 6.0 459 48 Example 74 D-3 5.0 6.0 459 49 Example 75 D-4 5.3 6.0 459 41 Example 76 D-5 5.3 5.9 459 42 Example 77 E-1 5.2 6.2 451 47 Example 78 E-2 4.3 6.1 459 43 Example 79 E-3 4.3 6.1 451 48 Example 80 E-4 5.3 6.0 469 43 Example 81 E-5 5.1 6.0 461 48 Example 82 F-1 5.3 6.0 461 49 Example 83 F-2 5.2 6.0 459 41 Example 84 F-3 5.0 6.2 451 42 Example 85 F-4 4.8 6.1 469 47 Example 86 F-5 5.1 6.0 461 47 Example 87 G-1 4.8 5.9 451 43 Example 88 G-2 5.1 6.2 459 48 Example 89 G-3 5.0 6.1 451 43 Example 90 G-4 4.8 6.1 469 48 Example 91 G-5 5.0 6.0 461 49 Comparative Example 5 - 4.8 6.0 461 49 Comparative Example 6 BCP 5.3 5.9 458 28

As shown in Table 3, the compounds A-1 to A-5, B-1 to B-5, C-1 to C-5, D-1 to D- (Examples 57 to 91) in which E-5, F-1 to F-5, and G-1 to G-5 were used as an electron transporting auxiliary layer material It was found that the current efficiency and lifetime were significantly improved as compared with the blue organic electroluminescent device (Comparative Example 5).

In addition, the blue organic electroluminescent devices (Examples 57 to 91) were superior in driving voltage and current efficiency to the blue organic electroluminescent device (Comparative Example 6) using conventional CBP as an electron transporting auxiliary layer material, Was remarkably improved.

[ Example  92 to 98] Blue organic Field  Fabrication of light emitting device

Compounds A-4, B-4, C-4, E-4, F-4 and G-4 synthesized in the above Synthesis Example were subjected to high purity sublimation purification by a conventionally known method, Thereby preparing a blue organic electroluminescent device.

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a UV OZONE cleaner (Power sonic 405, Hoshin Tech) And the substrate was transferred to a vacuum evaporator.

5% DS-405 (Doosan Electronics Co., Ltd.) (30 nm) / Compound A-95% of DS-205 (Doosan Electronics, 80 nm) / NPB 4, E-4, F-4 and G-4 (30 nm) Respectively.

[ Comparative Example  7]

A blue organic electroluminescent device was fabricated in the same manner as in Example 92 except that the compound A-4 was not used as the electron transport layer material.

[ Evaluation example  4]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices manufactured in Examples 92 to 98 and Comparative Example 7, and the results are shown in Table 4 below .

Sample Electron transport layer Driving voltage
(V) Current efficiency
(cd / A) Emission peak
(nm) Example 92 A-4 4.7 5.7 461 Example 93 B-4 4.2 6.0 457 Example 94 C-4 4.7 5.8 457 Example 95 D-4 4.2 5.8 457 Example 96 E-4 4.2 5.8 461 Example 97 F-4 4.2 5.8 461 Example 98 G-4 4.3 5.7 463 Comparative Example 7 _ 4.7 5.6 458

As shown in the above Table 4, the blue organic electric field using the compounds A-4, B-4, C-4, E-4, F-4 and G- It was found that the driving voltage and the current efficiency were further improved in the light emitting device (Examples 92 to 98) as compared with the blue organic electroluminescent device (Comparative Example 7) without using the electron transporting layer material.

As described above, it has been confirmed that when the compound according to the present invention is used not only as a light emitting layer material (host material) but also as an electron transporting layer material and an electron transporting layer material, the driving voltage and current efficiency are improved, .

Claims (8)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
A is a 6-membered aromatic ring or a 6-membered heteroaromatic ring,
B is a heteroaryl group having 5 to 60 nuclear atoms containing nitrogen,
X ₁ to X ₄ are the same or different and each independently N or C (R ₁ ), at least one of them being C (R ₁ )
R ₁ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group If, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ or of, or may be to the adjacent groups combine to form a fused ring, wherein said R ₁ is a plurality, They are the same or different from each other,
Ar ₁ and Ar ₂ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ An alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyl aryloxy group, C ₆ ~ aryloxy C _60, C group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ aryl of C ₆₀ boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ or, or a number, and to form the adjacent group fused ring ,
Alkyl group of the R _1, Ar ₁ and Ar _2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boronic A halogen atom, a cyano group, a nitro group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group of, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyl silyl group, C ₆ ~ aryl silyl group of C _60, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the aryl phosphine oxide group, and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylamine And when the substituent is plural, they may be the same or different from each other. The method according to claim 1,
The compound represented by the formula (1) is represented by any one of the following formulas (2) to (7).
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 2 to 7,
B, X ₁ to X ₄ , Ar ₁ and Ar ₂ are as defined in claim 1. The method according to claim 1,
And B is a substituent represented by the following formula (8).
[Chemical Formula 8]

In Formula 8,
* Represents a moiety bonded to Formula 1,
Y ₁ to Y ₅ are the same or different and each independently N or C (R ₂ ), wherein when R ₂ is plural, they are the same or different,
R ₂ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an arylamine, or a C _60, or may form a condensed ring adjacent tile,
Alkyl group of the R _2, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkylox A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of aryl amine group of the C ₆₀ And when the substituent is plural, they may be the same or different. The method of claim 3,
The substituent represented by the formula (8) is represented by any one of substituents represented by the following formulas (A1) to (A15).

In the above formulas A1 to A15,
R ₂ is as defined in claim 3,
m is an integer of 0 to 4,
R ₃ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₃ to C ₄₀ cycloalkyl, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having ₆ to ₆₀ carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy group , A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group , C ₆ ~ C ₆₀ aryl phosphine oxide group, and a C ₆ ~ selected from the group consisting of an arylamine, or a C _60, or may form a condensed ring adjacent tile,
Alkyl group of the R _3, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, arylphosphine oxide group and arylamine group are each independently selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ₂ to C ₄₀ alkenyl group, C ₂ to C ₄₀ alkynyl group, C ₃ to C ₄₀ A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkylox A C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ aryl phosphine oxide of the group and a C ₆ ~ value to one or more of the substituents selected from the group consisting of aryl amine group of the C ₆₀ And when the substituent is plural, they may be the same or different. The method according to claim 1,
Ar ₁ and Ar ₂ are the same or different and each independently represents a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, C ₆ ~ aryl silyl group of C _60, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine oxide of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the group, and a C ₆ ~ C _{60 &lt}; / RTI &gt; arylamine groups. An organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 5. The method according to claim 6,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer and an electron injecting layer. 8. The method of claim 7,
Wherein the organic compound layer containing the compound is a phosphorescent light-emitting layer, an electron transporting auxiliary layer, or an electron transporting layer.