KR20180071881A - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Abstract

The present invention relates to a novel compound and to an organic electroluminescent device comprising the same, wherein the compound, according to the present invention, is used in an organic layer of an organic electroluminescent device, and desirably, in an light-emitting layer, a hole-transporting layer, an electron-transporting layer or a life-improving layer, and thus can improve the light-emitting efficiency, driving voltage, life and the like of the organic electroluminescent device.

Description

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

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescence device and an organic electroluminescence device including the same.

The electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 were followed up with the observation of organic thin film emission from Bernanose in the 1950s. In 1987, Tang The organic light emitting device having a laminated structure in which the hole layer and the functional layer of the light emitting layer are divided. Thereafter, in order to form a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form in which each organic material layer has been introduced into 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 organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials to realize better natural colors. 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. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescence, the phosphorescent dopant as well as phosphorescent host materials are being studied extensively.

Up to now, hole injecting layer, hole transporting layer. NPB, BCP and Alq ₃ are widely known as electron transporting layer materials and anthracene derivatives as light emitting layer materials. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like having advantages in terms of efficiency improvement of the light emitting layer material are blue, green, (4,4-dicarbazolybiphenyl, CBP) is used as a phosphorescent dopant material for red phosphorescent dopants.

However, conventional organic layer materials have advantages in terms of light emission characteristics, but their thermal stability is not very good due to their low glass transition temperature, and thus they are not satisfactory in terms of lifetime of an organic electroluminescent device. Therefore, development of an organic layer material having excellent performance is required.

The present invention has been made to solve the above problems and it is an object of the present invention to provide a novel compound capable of improving the efficiency, lifetime and stability of the organic electroluminescent device and an organic electroluminescent device using the compound.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

R ₁ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of 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 ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ alkyl sulfonyl group, aryl sulfonyl group of a _{C 6 ~ C 60, C 1} ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group, C ₁ ~ C ₄₀ alkyl carbonyl group, C ₆ ~ C ₆₀ aryl carbonyl group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or of the number two substituents nuclear atoms bonded to each other to from 5 to 50 aromatic ring, nucleus atom adjacent 5 To 50 non-aromatic condensed polycyclic, An aromatic heterocycle having 5 to 50 nuclear atoms, or a non-aromatic condensed heterocyclic ring having 5 to 50 nuclear atoms;

m and n are each independently an integer of 0 to 2;

L ₁ and L ₂ are each independently a C ₆ to C ₁₈ arylene group or a heteroarylene group having 5 to 18 nucleus atoms and when a plurality of each of L ₁ and L ₂ are the same or different from each other;

X ₁ is O, S, Se, N (Ar ₂ ), C (Ar ₃ ) (Ar ₄ ) and Si (Ar ₅ ) (Ar ₆ );

Ar ₁ to Ar ₆ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, 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 ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ alkyl sulfonyl group, aryl sulfonyl group of a _{C 6 ~ C 60, C 1} ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group, C ₁ ~ C ₄₀ alkyl carbonyl A C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylamine group;

The aryl group and heteroarylene group of L ₁ and L ₂ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, and alkyloxy group of R ₁ to R ₁₂ and Ar ₁ to Ar ₆ An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, An aromatic ring, a non-aromatic condensed polycyclic aromatic heterocyclic ring, and a non-aromatic condensed heterocyclic ring formed by bonding a carbonyl group and an arylsilyl group with two adjacent substituents of R ₁ to R ₁₂ are each independently selected from deuterium, , A cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, An aryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl sulfonyl group of, C ₆ ~ C group of ₆₀ of the aryl sulfonyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group , A C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylsilyl group, and is substituted with a plurality of substituents They are the same as or different from each other.

The present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .

"Two adjacent substituents" in the present invention as R ₁ and R _2, R ₂ and R _3, R ₃ and R _4, R ₅ and R _6, R ₆ and R _7, R ₇ and R _8, R ₉ R ₁₀ , R ₁₀ and R ₁₁ , or R ₁₁ and R ₁₂ .

"Alkyl" in the present invention is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl And the like, but are not limited thereto.

As used herein, the term " alkenyl " is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, But are not limited to, allyl, isopropenyl, 2-butenyl, and the like.

The term " alkynyl " in the present invention is 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 thereof include ethynyl, , 2-propynyl, and the like, but are not limited thereto.

&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. Further, it is preferable that two or more rings are condensed with each other and only carbon atoms are contained as the ring-forming atoms (for example, the number of carbon atoms may be from 8 to 60) and the whole molecule is a non-aromacity monovalent Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. In addition, it is preferable that two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se besides carbon as a ring-forming atom, < / RTI > aromacity). Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as, for example, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, Click ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, " aryloxy " means a monovalent substituent represented by RO-, and R represents aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

The term " alkyloxy " in the present invention means a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and may be linear, branched or cyclic . ≪ / RTI > Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

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

&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 of the carbons, preferably one to three carbons, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

&Quot; Alkylsilyl " in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and " arylsilyl " means silyl substituted with aryl having 5 to 60 carbon atoms.

The term "aromatic ring" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Examples of such aromatic rings include, but are not limited to, phenyl, naphthyl, phenanthrenyl, anthrenyl, and the like.

The term "non-aromic condensed polycyclic" in the present invention refers to a non-aromatic condensed polycyclic ring having two or more rings condensed with each other and containing only carbon as a ring-forming atom, and the whole molecule having a non-aromacity Quot; means a group (e.g., having from 8 to 60 carbon atoms). Examples of the non-aromatic condensed polycyclic ring may include, but are not limited to, a fluorenyl group and the like.

&Quot; Aromatic heterocycle " in the present invention means a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein one or more carbons, preferably one to three carbons, of the ring are substituted with a heteroatom selected from N, O, P, S and Se. Also, two or more rings are pendant or condensed with each other, and include hetero atoms selected from N, O, P, S and Se in addition to carbon as a ring forming atom. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as, for example, phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, Click ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, the term "non-aromatic condensed heterocyclic ring" means that two or more rings are condensed with each other and contain heteroatoms selected from N, O, P and S in addition to carbon as a ring-forming atom, Means a group having non-aromacity (e.g., having from 2 to 60 carbon atoms). Examples of the non-aromatic condensed heterocyclic ring include, but are not limited to, a carbazolyl group and the like.

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

Since the compound of the present invention is excellent in thermal stability, carrier transport ability, light emitting ability, and the like, it can be effectively applied as an organic material layer material of an organic electroluminescent device.

In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel, etc. in terms of light emitting performance, driving voltage, lifetime and efficiency.

1 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 is a cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

R ₁ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of 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 ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ alkyl sulfonyl group, aryl sulfonyl group of a _{C 6 ~ C 60, C 1} ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group, C ₁ ~ C ₄₀ alkyl carbonyl group, C ₆ ~ C ₆₀ aryl carbonyl group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or of the number two substituents nuclear atoms bonded to each other to from 5 to 50 aromatic ring, nucleus atom adjacent 5 To 50 non-aromatic condensed polycyclic, An aromatic heterocycle having 5 to 50 nuclear atoms, or a non-aromatic condensed heterocyclic ring having 5 to 50 nuclear atoms;

m and n are each independently an integer of 0 to 2;

L ₁ and L ₂ are each independently a C ₆ to C ₁₈ arylene group or a heteroarylene group having 5 to 18 nucleus atoms and when a plurality of each of L ₁ and L ₂ are the same or different from each other;

X ₁ is O, S, Se, N (Ar ₂ ), C (Ar ₃ ) (Ar ₄ ) and Si (Ar ₅ ) (Ar ₆ );

Ar ₁ to Ar ₆ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, 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 ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ alkyl sulfonyl group, aryl sulfonyl group of a _{C 6 ~ C 60, C 1} ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group, C ₁ ~ C ₄₀ alkyl carbonyl A C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylamine group;

The aryl group and heteroarylene group of L ₁ and L ₂ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, and alkyloxy group of R ₁ to R ₁₂ and Ar ₁ to Ar ₆ An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, An aromatic ring, a non-aromatic condensed polycyclic aromatic heterocyclic ring, and a non-aromatic condensed heterocyclic ring formed by bonding a carbonyl group and an arylsilyl group with two adjacent substituents of R ₁ to R ₁₂ are each independently selected from deuterium, , A cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, An aryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl sulfonyl group of, C ₆ ~ C group of ₆₀ of the aryl sulfonyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group , A C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylsilyl group, and is substituted with a plurality of substituents They are the same as or different from each other.

The novel compounds according to the present invention include diindolo phenothiazine moieties, diindolo phenoxazine moieties, or diindolo acridine moieties. And is characterized by being represented by the above formula (1). The compound represented by the formula (1) has higher molecular weight than the conventional organic electroluminescence device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')] and has a high glass transition temperature.

In addition, because phenyl is coupled with phenothiazine through the condensation structure of phenothiazine and indole, it is more flat and widened the conjugation region. Therefore, it has excellent thermal stability, and has excellent hole injection ability, hole transport ability, great. Therefore, when the compound of Formula 1 is included in the organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.

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 Formula 1 can be used as a host material because a specific substituent is introduced into a condensed indole derivative having a broad singlet energy level and a high triplet energy level so that the energy level can be controlled higher than that of the dopant.

In the present invention, the diindolophenothiazine moiety, the diindolo-phenoxazione moiety, or the diindoloacridine moiety may have a moiety having good hole transport ability and a mobility The compound of the present invention has hole mobility or electron mobility of more than a certain level and can be used as a hole transporting layer of an organic electroluminescent device.

In addition, since the compound of Formula 1 has a structure in which an electron-withdrawing group (EWG) having a high electron absorbing property is bonded, the entire molecule has bipolar characteristics, so that the binding force between holes and electrons can be enhanced. Therefore, the compound of the formula (1) can exhibit excellent luminescent characteristics and can be applied to a blue, green or red phosphorescent light-emitting layer material of an organic electroluminescent device.

As described above, the compound represented by Formula 1 can improve phosphorescence characteristics of the organic electroluminescent device, improve the hole injection / transport ability, luminous efficiency, driving voltage, lifetime characteristics, etc., The electron transporting ability and the like can be improved. Therefore, the compound of Chemical Formula (1) according to the present invention is useful as an organic layer material of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), a hole and electron transporting layer material, , And more preferably as a phosphorescent light-emitting layer material.

In addition, the compound of formula (1) has various substituents, especially aryl groups and / or heteroaryl groups, introduced into the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, For example, CBP). ≪ / RTI > The compound represented by the formula (1) is also effective for inhibiting crystallization of the organic material layer. Therefore, the organic electroluminescent device comprising the compound of Formula 1 according to the present invention can greatly improve performance and lifetime characteristics. As a result, the organic light emitting device having improved performance and lifetime characteristics can maximize the performance of the full color organic light emitting panel.

That is, when the compound of Formula 1 according to the present invention is used as a hole and electron injection / transport layer material of an organic electroluminescent device or a blue, green and / or red phosphorescent host material, a conventional organic layer material (for example, CBP) The efficiency and lifetime of the organic 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.

The formula (1) of the present invention can be represented by the following structures, but is not limited thereto.

According to a preferred embodiment of the present invention, each of R ₁ to R ₁₂ independently represents hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, 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 of, C ₆ ~ C ₆₀ of the aryloxy group, C group ₃ ~ C ₄₀ alkylsilyl, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ alkylsulfonyl group of C _40, C ₆ An arylsulfonyl group having ₁ to ₆₀ carbon atoms, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphonyl group, a C ₆ to C ₆₀ mono or diarylphosphine A C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylamine group,

Alkyl group of the R ₁ to R _12, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkylsulfonyl group, an aryl An arylcarbonyl group, an arylcarbonyl group and an arylsilyl group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C _{1 to} C ₆ alkyl group, an arylcarbonyl group, an aryloxycarbonyl group, a ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of the An aryloxy group of C ₁ to C ₄₀ , an arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, C ₆ ~ C ₆₀ aryl sulfonyl group, C ₁ ~ C ₄₀ aryl group of an alkyl boron, C ₆ ~ C ₆₀ boron group, C ₆ ~ C ₆₀ A C ₆ to C ₆₀ mono or diarylphosphinyl group, a C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylsilyl group, And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, when the compound according to the present invention is applied to a material of an organic electroluminescent device, considering the luminescent characteristics, R ₁ to R ₁₂ are each independently hydrogen, C ₁ to C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and a nuclear atoms selected from 5 to 60 heteroaryl group the group consisting of, more preferably C ₆ ~ C ₆₀ aryl group or a nuclear atoms of 5 to 60 heteroaryl group Lt;

The alkyl, aryl and heteroaryl groups of R ₁ to R ₁₂ are each independently selected from the group consisting of 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. When substituted with a plurality of substituents, they may be the same as or different from each other.

According to a more preferred embodiment of the present invention, each of R ₁ to R ₁₂ independently represents a hydrogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a biphenyl group, a terphenyl group, There can be mentioned a phenol compound such as phenylene, phenanthrene, fluorene, cryogen, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, Benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, benzothiazole, benzothiazole, benzothiazole, benzothiazole, benzothiazole, benzothiazole, , Cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, phthyridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine , More preferably phenyl, biphenyl , Terphenyl, naphthalene, pyridine, pyridazine, pyrimidine, pyrazine and triazine.

According to a preferred embodiment of the present invention, R ₇ and R ₁₀ in Formula 1 are each independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, There can be mentioned naphthalene, triphenylene, phenanthrene, fluorene, cryogen, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, The present invention relates to a process for producing a compound represented by the general formula (1), wherein the compound is selected from the group consisting of a thiazole, a thiazole, a thiazole, a dioxazole, a thiadiazole, a pyridine, a pyridazine, a pyrimidine, , Isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, phthyridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine , And more preferably selected from the group consisting of A cow, phenyl, biphenyl, terphenyl, naphthalene, pyridine, pyridazine, pyrimidine, pyrazine, and may be selected from the group consisting of a triazine, and more preferably R ₇ and R ₁₀ either of which is hydrogen, and the other One may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, pyridine, pyridazine, pyrimidine, pyrazine and triazine.

According to a preferred embodiment of the present invention, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , R ₇ and R ₈ and R ₉ , R ₁₀ , R ₁₀ and R _11, and at least one of R ₁₁ and R ₁₂ may each independently be bonded to a ring represented by the following formula (2) to form a condensed ring:

(2)

In Formula 2,

The dotted line means a moiety in which the condensation is carried out in the above formula (1);

Z ₁ to Z ₄ are each independently N or C (Ar ₂ );

Ar ₂ 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 alkylsulfonyl group, a C ₆ to C ₆₀ arylsulfonyl group, a C ₁ to C ₄₀ alkylboron group , A C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, a C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ aryl carbonyl group and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of or, wherein the Ar ₂ is nuclear atoms two Ar ₂ are bonded to each other adjacent if multiple individuals from 5 to 50 aromatic ring, nucleus atoms Several 5 to 50 non-aromatic condensed polycyclic, An aromatic heterocycle having 5 to 50 nuclear atoms, or a non-aromatic condensed heterocyclic ring having 5 to 50 nucleus atoms, and a plurality of Ar _{2 s} may be the same as or different from each other;

Alkyl group of said Ar _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl sulfonyl group, aryl sulfonyl group, An aryloxy group, an arylboron group, an arylphosphonyl group, a mono- or diarylphosphinyl group, an alkylcarbonyl group, an arylcarbonyl group, and an arylsilyl group, an aromatic ring formed by bonding two adjacent Ar ₂ groups, Aromatic condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heterocyclic ring are 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 C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, the aryl sulfonyl group of a _{C 6 ~ C 60, C 1} ~ C 40 group of an alkyl boron, C ₆ ~ aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group, C ₁ ~ C ₄₀ alkyl carbonyl, C of ₆ ~ C ₆₀ aryl carbonyl group and a C ₆ ~ aryl of C ₆₀ A silyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , R ₇ and R ₈ and R ₉ , R ₁₀ , R ₁₀ and R _11, and any one of R ₁₁ and R ₁₂ may be bonded to the ring represented by Formula 2 to form a condensed ring.

According to a preferred embodiment of the present invention, R ₉ and R ₁₀ may be bonded to the ring represented by Formula 2 to form a condensed ring.

According to a preferred embodiment of the present invention, in Formula 2, each of Z ₁ to Z ₄ is independently C (Ar ₂ )

Wherein Ar ₂ 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 group ₃ ~ C ₄₀ alkylsilyl, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ alkyl sulfonyl, C of ₆ ~ C ₆₀ aryl sulfonyl group, alkyl of C ₁ ~ C ₄₀ boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, a C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group, an alkyl carbonyl group of C ₁ ~ C _40, C ₆ ~ C ₆₀ aryl carbonyl group and C ~ ₆ is selected from the group consisting of an aryl amine of the C _60;

Alkyl group of said Ar _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl sulfonyl group, aryl sulfonyl group, An arylcarbonyl group, an arylcarbonyl group and an arylsilyl group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, an aryloxy group, an aryloxy group, the alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, an aryloxy group of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of the , An alkyloxy group of C ₁ to C ₄₀ , an arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group , A C ₁ to C ₄₀ alkylsulfonyl group, a C ₆ to C ₆₀ arylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ aryl A C ₆ -C ₆₀ mono- or diarylphosphinyl group, a C ₁ -C ₄₀ alkylcarbonyl group, a C ₆ -C ₆₀ arylcarbonyl group, and a C ₆ -C ₆₀ arylsilyl group in the group consisting of And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, in the formula ( ₂ ), each of Z ₁ to Z ₄ is independently C (Ar ₂ )

Wherein Ar ₂ is 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 ring atoms;

The alkyl, aryl and heteroaryl groups of Ar ₂ are each independently substituted with at least one substituent selected from the group consisting of 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 , And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, m and n may each independently be 0 or 1.

According to a preferred embodiment of the present invention, L ₁ and L ₂ may be a conventional divalent group linker known in the art. More specifically, L ₁ and L ₂ are each a linker A substituted or unsubstituted monovalent hydrocarbon group, a substituted or unsubstituted monovalent hydrocarbon group, a substituted or unsubstituted monovalent hydrocarbon group, a substituted or unsubstituted monovalent hydrocarbon group, a substituted or unsubstituted monovalent monovalent hydrocarbon group, a substituted or unsubstituted monovalent monovalent hydrocarbon group, L ₁ and L ₂ are each independently selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, an alkoxy group, an alkoxycarbonyl group, an alkoxycarbonyl group, an alkoxycarbonyl group, May be a linker selected from the group consisting of formulas K-1 to K-4:

In the above formulas (K-1) to (K-4)

* Means the part where the combination is made.

According to a preferred embodiment of the present invention, when the compound according to the present invention is applied to a material for an organic electroluminescent device, considering the luminescent properties, Ar ₁ is a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ An aryl group and a heteroaryl group having 5 to 60 nuclear atoms, more preferably an aryl group having ₆ to ₆₀ carbon atoms or a heteroaryl group having 5 to 60 nuclear atoms;

The alkyl, aryl and heteroaryl groups of Ar ₁ are each independently substituted with at least one substituent selected from the group consisting of 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 , And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to one more preferred embodiment of the present invention, Ar ₁ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Thiazole, thiazole, thiazole, oxadiazole, oxytriazole, dioxazole, oxazole, thiazole, thiazole, thiazole, Benzothiazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxine, quinazoline, quinazoline, quinazoline, quinazoline, quinazoline, May be selected from the group consisting of salicyl, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine, Such as phenyl, biphenyl, terphenyl, naphthalene, pyridine, Lee pyridazine, pyrimidine, are selected from the group consisting of pyrazine and triazine;

Examples of the substituent of the above-mentioned Ar ₁ include methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine , Pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, Benzothiopyrimidine, benzothienopyridine and thienodipyridine are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a nucleus A heteroaryl group having 5 to 60 atoms and substituted with at least one substituent selected from the group consisting of And when they are unsubstituted or substituted with a plurality of substituents, they may be the same or different.

According to a more preferred embodiment of the present invention, Ar ₁ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Thiazole, thiazole, thiazole, oxadiazole, oxytriazole, dioxazole, oxazole, thiazole, thiazole, thiazole, Benzothiazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxine, quinazoline, quinazoline, quinazoline, quinazoline, quinazoline, May be selected from the group consisting of salicyl, naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine, Such as phenyl, biphenyl, terphenyl, naphthalene, pyridine, Lee pyridazine, pyrimidine, are selected from the group consisting of pyrazine and triazine;

Examples of the substituent of the above-mentioned Ar ₁ include methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine , Pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, And the thienodipyridine are each independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a phenyl group, Biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, chrysene, Benzopyran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine , Pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, Which is unsubstituted or substituted with at least one substituent selected from the group consisting of benzothiophene, benzothiophene, phthalazine, phthiridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine, When they are substituted with a plurality of substituents, they may be the same or different.

According to one most preferred embodiment of the present invention, Ar < ₁ > may be a substituent represented by the following formula (3) or (4)

(3)

[Chemical Formula 4]

In the above formulas (3) and (4)

* Denotes the part where the bond is made;

Z ₅ to Z ₉ are each independently N or C (Ar ₇ );

s is an integer from 0 to 4;

R ₄ is 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 alkynyl, C ₃ to C ₄₀ cycloalkyl, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, an aryloxy group of a C ₆ ~ C ₆₀ of, C _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 arylphosphonyl group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination group adjacent to form a condensed ring, when individual said R ₄ is a plurality, they are equal to each other Or different;

Ar ₇ 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 arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination groups adjacent when forming a condensed ring, and individual said Ar ₇ is a plurality which the Are the same or different from each other;

Alkyl groups of the R ₄ and Ar _7, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of When they are substituted or unsubstituted with one or more substituents, and when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to one more preferred embodiment of the present invention, when the compound according to the present invention is used as a material for the hole transport layer, Z ₅ to Z ₉ are each independently C (Ar ₇ ) in terms of light emitting properties.

According to a more preferred embodiment of the present invention, when the compound according to the present invention is used as a material for an electron transport layer, at least one of Z ₅ to Z ₉ is N in the general formula (3) At least one of Z ₅ to Z ₇ is preferably N in light emitting property.

According to one more preferred embodiment of the present invention, the substituent represented by the general formula (3) may be a substituent represented by the following general formula

[Chemical Formula 5]

In Formula 5,

* Denotes the part where the bond is made;

R ₅ and R ₆ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, 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 ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, it said shed some light selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of;

Alkyl groups of the R ₅ and R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with a plurality of substituents, they are the same as or different from each other;

Each of Z ₁ , Z ₃ and Z ₅ is as defined in the above formula (3).

According to a preferred embodiment of the present invention, the substituent represented by the formula (3) may be a substituent represented by any one of the following formulas (L-1) to (L-3)

In the above formulas (L-1) to (L-3)

* Denotes the part where the bond is made,

R ₅ and R ₆ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, 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 ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;

Alkyl groups of the R ₅ and R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₅ and R ₆ are each independently selected from the group consisting of 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 Selected;

The alkyl, aryl and heteroaryl groups of R ₅ and R ₆ are each independently selected from the group consisting of 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. And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₅ and R ₆ are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, And examples thereof include phenanthrene, fluorene, cryogen, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole , Dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, , Quinazoline, quinoxaline, naphthyridine, phthalazine, phthyridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine ;

Examples of the R ₅ and R ₆ groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine , Pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine , Benzothienopyridine, thienodipyridine, benzothienopyridine and thienodipyridine are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, And a heteroaryl group having 5 to 60 nucleus atoms and at least one substituent selected from the group consisting of When they are substituted or unsubstituted and are substituted by a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, R ₅ and R ₆ are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, And examples thereof include phenanthrene, fluorene, cryogen, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole , Dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, , Quinazoline, quinoxaline, naphthyridine, phthalazine, phthyridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine ;

Examples of the R ₅ and R ₆ groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine , Pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine , Phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine are each independently a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group , Phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, Benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, benzothiophene, Benzothiazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, quinazoline, quinazoline, quinoxaline, quinoxaline, Which is substituted or unsubstituted with at least one substituent selected from the group consisting of naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a more preferred embodiment of the present invention, R ₅ and R ₆ are each independently selected from phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, di Is selected from the group consisting of benzofuran, benzofuran, benzothiophene, pyridine, pyridazine, pyrimidine, pyrazine, and triazine;

The above-mentioned R ₅ and R ₆ phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyridine, pyridazine , Pyrimidine, pyrazine and triazine are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene , Pyridine, pyridazine, pyrimidine, pyrazine, and triazine, and when they are substituted with a plurality of substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, the substituent represented by Formula 4 may be a substituent represented by Formula 6:

[Chemical Formula 6]

In Formula 6,

* Denotes the part where the bond is made;

s, R < ₄ > and Ar < ₇ >

According to a preferred embodiment of the present invention, Ar ₇ and R ₄ are each independently a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroatom having 5 to 60 nuclear atoms An aryl group;

The alkyl, aryl and heteroaryl groups of Ar ₇ and R ₄ are each independently selected from the group consisting of 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. And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, Ar ₇ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, The compounds of formula (I) may be selected from the group consisting of aldehydes, aldehydes, ketones, carbenes, dyes, carbenes, dibenzothiophenes, carbazoles, dibenzofurans, benzofurans, benzothiophenes, pyrazoles, imidazoles, triazoles, oxazoles, thiazoles, oxadiazoles, The present invention relates to a process for the production of quinoxaline, quinoxaline, quinoxaline, quinoxaline, quinoline, quinoline, quinoline, quinoline, quinoline, quinoxaline, quinoxaline, , Naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine,

Examples of the substituent of Ar _{7 include} a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, cryogen, dibenzothiophene, carbazole , Dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine , Pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, Benzothiopyrimidine, benzothienopyridine and thienodipyridine are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a nucleus A heteroaryl group having 5 to 60 atoms and substituted with at least one substituent selected from the group consisting of Or when they are unsubstituted or substituted with a plurality of substituents, they are the same as or different from each other.

According to a preferred embodiment of the present invention, Ar ₇ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, The compounds of formula (I) may be selected from the group consisting of aldehydes, aldehydes, ketones, carbenes, dyes, carbenes, dibenzothiophenes, carbazoles, dibenzofurans, benzofurans, benzothiophenes, pyrazoles, imidazoles, triazoles, oxazoles, thiazoles, oxadiazoles, The present invention relates to a process for the production of quinoxaline, quinoxaline, quinoxaline, quinoxaline, quinoline, quinoline, quinoline, quinoline, quinoline, quinoxaline, quinoxaline, , Naphthyridine, phthalazine, pteridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine,

Examples of the substituent of Ar _{7 include} a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, cryogen, dibenzothiophene, carbazole , Dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine , Pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, And the thienodipyridine are each independently selected from the group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a phenyl group, a phenyl group, Biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, chrysene, Benzopyran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine , Pyridazine, pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, Which is unsubstituted or substituted with at least one substituent selected from the group consisting of benzothiophene, benzothiophene, phthalazine, phthiridine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine, When they are substituted with a plurality of substituents, they may be the same or different.

According to a more desired embodiment, the Ar ₇ are each independently selected from phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, dibenzofuran, Benzofuran, benzothiophene, pyridine, pyridazine, pyrimidine, pyrazine, and triazine,

The above-mentioned Ar ₇ phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, pyridine, pyridazine, pyrimidine , Pyrazine and triazine are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, naphthalene, triphenylene, phenanthrene, fluorene, dibenzothiophene, carbazole, dibenzofuran, benzofuran, benzothiophene, Substituted or unsubstituted with at least one substituent selected from the group consisting of pyridazine, pyrimidine, pyrazine and triazine, and when they are substituted with a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, the Ar ₃ And Ar ₄ are each independently selected from the group consisting of 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;

The alkyl, aryl and heteroaryl groups of Ar ₃ and Ar ₄ are each independently selected from the group consisting of 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. And when they are substituted with a plurality of substituents, they are the same as or different from each other.

According to a more preferred embodiment of the present invention, the Ar ₃ And Ar ₄ are each independently selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Carbazole, dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine , Pyrimidine, pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine , Phthalidine, xanthene, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine and thienodipyridine, and more preferably Ar ₃ And Ar ₄ each independently may be selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, pyridine, pyridazine and pyrimidine.

The compounds represented by formula (1) of the present invention can be represented by the following compounds, but are not limited thereto:

The compounds of formula 1 of the present invention can be synthesized according to the general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995 ). Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic Field  Light emitting element

Another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the general formula (1) according to the present invention described above.

Specifically, the present invention is an organic electroluminescent device comprising an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes Include compounds represented by the above formula (1). At this time, the compounds may be used singly 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 layer, a light emitting auxiliary layer, a life improving layer, an electron transporting layer, an electron transporting auxiliary layer and an electron injecting layer, 1 < / RTI >

The structure of the organic electroluminescent device according to the present invention is not particularly limited. For example, referring to FIG. 1, an anode 10 and a cathode 20 facing each other, 20). ≪ / RTI > Here, the organic layer 30 may include a hole transport layer 31, a light emitting layer 32, and an electron transport layer 34. A hole transporting auxiliary layer 33 may be interposed between the hole transporting layer 31 and the light emitting layer 32. An electron transporting auxiliary layer 35 may be interposed between the electron transporting layer 34 and the light emitting layer 32 can do.

2, the organic layer 30 may further include a hole injection layer 37 between the hole transport layer 31 and the anode 10, and the electron transport layer 34 and the cathode And an electron injection layer (36) may be further included between the first electrode (20) and the second electrode (20).

In the present invention, the hole injection layer 37 deposited between the hole transport layer 31 and the anode 10 improves the interfacial properties between the ITO used as the anode and the organic material used as the hole transport layer 31 But the surface of the ITO layer is applied to the upper surface of the ITO which is not planarized to soften the surface of the ITO. The layer can be used without any particular limitation as long as it is commonly used in the art. For example, an amine compound can be used But is not limited thereto.

The electron injection layer 36 is a layer which is stacked on the electron transport layer 34 to facilitate injection of electrons from the cathode to ultimately improve power efficiency and is commonly used in the art . For example, materials such as LiF, Liq, NaCl, CsF, Li ₂ O, and BaO can be used.

In addition, although not shown in the drawings, the light emitting layer 32 may further include a light emitting auxiliary layer between the hole transporting auxiliary layer 33 and the light emitting layer 32. The light-emission-assisting layer may serve to adjust the thickness of the organic layer 30 while serving to transport holes to the light-emitting layer 32. The light-emission-assisting layer may include a hole-transporting material and may be made of the same material as the hole-transporting layer 31.

In addition, although not shown in the drawings, a life improving layer may be further included between the electron transporting auxiliary layer 35 and the light emitting layer 32. Holes moving in the organic light emitting device due to the ionization potential level in the light emitting layer 32 are blocked by the high energy barrier of the lifetime enhancing layer and do not diffuse or move to the electron transporting layer and consequently function to limit the holes to the light emitting layer . The function of restricting the holes to the light emitting layer prevents diffusion of holes to the electron transporting layer that transports electrons by reduction, thereby suppressing the lifetime degradation due to the irreversible decomposition reaction by oxidation and contributing to improvement in the lifetime of the organic light emitting device .

In the present invention, the compound represented by the formula (1) may be a diindolo phenothiazine moiety, a diindolo phenoxazine moiety, or a diindolo acridine moiety In particular, the diindolophenothiazine moiety is a condensation structure of phenothiazine and indole, and since the phenyl of the amine is linked to phenothiazine, the conjugation region is widened as it is more flat. Excellent in hole injecting ability, hole transporting ability, and light emitting ability. Therefore, when the compound of Formula 1 is included in the organic electroluminescent device, the driving voltage, efficiency, lifetime, etc. of the device can be improved.

In the present invention, the compound represented by the formula (1) can be controlled to have a higher energy level than the dopant by introducing a specific substituent to the condensed indole derivative having a broad singlet energy level and a high triplet energy level, .

In the present invention, the diindolophenothiazine moiety, the diindolo-phenoxazione moiety, or the diindoloacridine moiety may have a moiety having good hole transport ability and a mobility The compound of the present invention has hole mobility or electron mobility of more than a certain level and can be used as a hole transporting layer of an organic electroluminescent device.

As described above, the compound represented by Formula 1 can improve phosphorescence characteristics of the organic electroluminescent device, improve the hole injection / transport ability, luminous efficiency, driving voltage, lifetime characteristics, etc., The electron transporting ability and the like can be improved. Accordingly, the compound of Formula 1 according to the present invention can be used as an organic layer material of an organic electroluminescent device, preferably a light emitting layer (blue, green and / or red phosphorescent host material), a light emitting auxiliary layer, a hole transporting layer, , An electron injection layer or a life improving layer, and more preferably, it can be used as a material for a light emitting layer, a hole transporting layer, an electron transporting layer or a life improving layer, and more preferably a phosphorescent light emitting layer material.

In addition, the organic electroluminescent device according to the present invention may further include an insulating layer or an adhesive layer at the interface between the electrode and the organic layer as well as the anode, one or more organic layers and the cathode sequentially laminated as described above.

The organic electroluminescent device of the present invention includes materials and methods known in the art, except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer) is formed to include the compound represented by Formula 1 To form another organic material layer and an electrode.

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 usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

The anode material may be made of a conductor having a high work function to facilitate injection of holes, for example, 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as 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.

The negative electrode material may be made of a conductor having a low work function so as to facilitate electron injection and may be made of a material having a low work function such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, The same metal or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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

Example

[ Preparation Example  One] IPT Synthesis of -1

<Step 1> Synthesis of 10- (2- Bromophenyl ) -10H- Phenothianazine  synthesis

(100 g, 501.8 mmol), 1-bromo-2-iodobenzene (170.4 g, 602.2 mmol), Cu (15.9 g, 250.9 mmol) and K ₂ CO ₃ (138.7 g, 1003.7 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 캜 for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to remove moisture with MgSO _4. 10- (2- (96 g, yield 54%) was obtained.

^{1 H-NMR: δ 6.97 (} m, 2H), 7.07-7.23 (m, 9H), 7.66 (d, 1H)

<Step 2> Indolo [3,2,1-cl] phenothiazine &lt; / RTI &gt;  synthesis

(96 g, 271 mmol), Pd (OAc) ₂ (6.1 g, 27.1 mmol), PCy ₃ HBF ₄ (20g, 54.2 mmol), K 2 CO 3 (74.9 g, 542.1 mmol) and DMA (1500 ml) were mixed and stirred at 170 占 폚 for 3 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 resulting organic layer and purified by column chromatography (Hexane: EA = 6: 1 (v / v)) to give indolo [3,2,1-kl] phenothiazine (67.4 g, yield 91% .

^{1 H-NMR: δ 6.97-7.01 (} m, 2H), 7.11-7.2 (m, 3H), 7.32 (t, 1H), 7.51 (t, 1H), 7.63 (d, 1H), 7.84 (d, 1H ), 8.00-8.03 (m, 2H)

<Step 3> 8- Bromoindolo [3,2,1-kl] phenothiazine &lt; RTI ID = 0.0 &gt;  synthesis

[3,2,1-kl] phenothiazine (67.4 g, 246.6 mmol), NBS (43.9 g, 246.6 mmol) and methylene chloride (1000 ml) were added dropwise at 0 ° C under a nitrogen stream at room temperature for 12 hours 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 = 6: 1 (v / v)) to obtain 8- -kl] phenothiazine (65.1 g, yield 75%).

^{1 H-NMR: δ 6.85 (} d, 1H), 7.04 (t, 1H), 7.19-7.2 (m, 2H), 7.31 (d, 1H), 7.39 (t, 1H), 7.57 (t, 1H), 7.85 (d, 1 H), 8.04 (d, 1 H), 8.74 (d, 1 H)

<Step 4> Synthesis of 8- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) indolo [3,2,1-kl] phenothiazine

Bromoindolo [3,2,1-kl] phenothiazine (65.1 g, 185 mmol), 4,4,4 ', 4', 5,5,5 ' (51.2 g, 203.4 mmol), Pd (dppf) Cl ₂ (16.2 g, 18.5 mmol), KOAc (52.2 g, 554.9 mmol) ) And 1,4-dioxane (1000 ml) were mixed and stirred at 130 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to remove moisture with MgSO ₄ . Methyl-1,3,2-dioxabororen-2-yl) indolo [3,2,1-kl] phenothiazine (59.8 g, yield 81%).

¹ H-NMR:? 1.20 (s, 12H), 7.19-7.21 (m, 3H), 7.43-7.58

&Lt; Step 5 > 8- (2-nitrophenyl) indolo [3,2,1-kl] phenothiazine  synthesis

A solution of 8- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) indolo [3,2,1-kl] phenothiazine (59.8 g , 149.8 mmol), 1- bromo-2-nitrobenzene (36.3 g, 179.8 mmol), Pd (PPh 3) 4 (8.7 g, 7.5 mmol), K 2 CO 3 (41.4 g, 299.6 mmol) and 1,4-dioxane / H ₂ O (500 ml / 100 ml) 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 = 5: 1 (v / v)) to obtain 8- (2-nitrophenyl) indolo [3,2,1- kl] phenothiazine 38.4 g, yield 65%).

^{1 H-NMR: δ 7.19-7.21 (} m, 3H), 7.44-7.58 (m, 5H), 7.72 (t, 1H), 7.89 (t, 1H), 8.00-8.03 (m, 3H), 8.19 (d , 1H)

<Step 6> IPT Synthesis of -1

(3,2,1-kl) phenothiazine (38.4 g, 97.4 mmol), triphenylphosphine (63.9 g, 243.4 mmol) and 1,2-dichloro Benzene (500 ml) was added thereto, followed by stirring 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 purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain IPT-1 (25.8 g, yield 73%).

¹ H-NMR of IPT-1:? 7.05 (t, 1H), 7.21-7.30 (m, 3H), 7.36 (d, 1H), 7.43-7.51 (d, IH), 8.16 (d, IH), 8.24 (b, IH), 8.66

[ Preparation Example  2] IPT Synthesis of -2

<Steps 1 to 4> Preparation Example Stage 1  Same as 1 to 4

&Lt; Step 5 > 8- (2-nitronaphthalen-1-yl) indole [3,2,1- kl ] Phenothiazine  Synthesis of

A solution of 8- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) indolo [3,2,1-kl] phenothiazine (59.8 g , 149.8 mmol), 1- bromo-2-nitro naphthalene (45.3 g, 179.8 mmol), Pd (PPh 3) 4 (8.7 g, 7.5 mmol), K 2 CO 3 (41.4 g, 299.6 mmol) and 1,4-dioxane / H ₂ O (500 ml / 100 ml) 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 = 5: 1 (v / v)) to obtain 8- (2-nitronaphthalen-1-yl) indolo [ Phenothiazine (40.6 g, yield 61%).

^{1 H-NMR: δ 7.19-7.21 (} m, 3H), 7.44-7.58 (m, 6H), 7.72 (t, 1H), 8.02-808 (m, 2H), 8.19-8.25 (m, 2H), 8.76 (d, 1 H), 9.10 (d, 1 H)

<Step 6> IPT Synthesis of -2

Phenothiazine (40.6 g, 91.4 mmol), triphenylphosphine (60 g, 228.5 mmol), and 1 (2-nitronaphthalen-1-yl) indolo [ , And 2-dichlorobenzene (500 ml) were added thereto, followed by stirring 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 purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain IPT-2 (24.5 g, yield 65%).

The ^{IPT-2 1 H-NMR:} δ 7.05 (t, 1H), 7.21-7.30 (m, 3H), 7.36 (d, 1H), 7.43-7.51 (m, 4H), 7.58-7.61 (m, 2H) , 8.16 (d, IH), 8.24 (b, IH), 8.66

[ Preparation Example  3] IPT Synthesis of -3

<Steps 1 to 4> Preparation Example Stage 1  Same as 1 to 4

Step 5 Synthesis of 8- (4-nitro- [1,1'-biphenyl] -3-yl) indolo [3,2,1-kl] phenothiazine

A solution of 8- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) indolo [3,2,1-kl] phenothiazine (59.8 g , 149.8 mmol), 3- bromo-4-nitro-1,1'-biphenyl (50.0 g, 179.8 mmol), Pd (PPh 3) 4 (8.7 g, 7.5 mmol), K 2 CO 3 (41.4 g, 299.6 mmol) and 1,4-dioxane / H ₂ O (500 ml / 100 ml) 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 = 5: 1 (v / v)) to give 8- (4-nitro- [1,1'-biphenyl] [3,2,1-kl] phenothiazine (44.4 g, yield 63%).

^{1 H-NMR: δ 7.19-7.21 (} m, 3H), 7.41-7.58 (m, 8H), 7.75 (d, 2H), 7.89 (d, 1H), 8.02 (d, 1H), 8.19-8.20 (m , 2H), 8.55 (d, 1 H)

<Step 6> IPT Synthesis of -3

[3,2,1-kl] phenothiazine (44.4 g, 94.4 mmol) and triphenylphosphine (2-hydroxyethyl) (61.9 g, 236.0 mmol) and 1,2-dichlorobenzene (500 ml) were added thereto, followed by stirring 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 purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain IPT-3 (28.6 g, yield 69%).

¹ H-NMR of IPT-3:? 7.02 (s, 1H), 7.19-7.20 (m, 2H), 7.41-7.58 (m, 8H), 7.75-7.77 , 7.99 (d, IH), 8.19 (d, IH), 8.32 (b, IH)

[ Preparation Example  4] IPT Synthesis of -4

<Step 1> Synthesis of 10- (3- Bromo - [1,1'-biphenyl] -4-yl) -10H- Phenothianazine  synthesis

Iodine-1,1'-biphenyl (216.2 g, 602.2 mmol), Cu (15.9 g, 250.9 mmol), K ₂ CO ₃ (138.7 g, 1003.7 mmol) and nitrobenzene (2000 ml) 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 = 10: 1 (v / v)) to obtain 10- (3- -Biphenyl] -4-yl) -10H-phenothiazine (103.7 g, yield 48%).

^{1 H-NMR: δ 6.97 (} m, 2H), 7.16-7.26 (m, 7H), 7.41-7.49 (m, 5H), 7.75 (m, 2H)

<Step 2> 10- Phenylindolo [3,2,1-kl] phenothiazine &lt; RTI ID = 0.0 &gt;  synthesis

10H-phenothiazine (103.7 g, 240.9 mmol) and Pd (OAc) ₂ (5.4 g, 24.1 mmol) in a stream of nitrogen under a stream of 10- ), PCy ₃ HBF ₄ (17.7 g, 48.2 mmol), K 2 CO 3 (66.6 g, 481.8 mmol) and DMA (1500 ml) were mixed and stirred at 170 占 폚 for 3 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 resulting organic layer, and the residue was purified by column chromatography (Hexane: EA = 6: 1 (v / v)) to give 10-phenylindolo [3,2,1-kl] phenothiazine (71.5 g, yield 85 %).

¹ H-NMR:? 7.02-7.05 (m, 2H), 7.19 (t, 1H), 7.41-7.53 (m, 6H), 7.75-7.77 , &Lt; / RTI &gt; 1H), 8.29 (d, 1H)

<Step 3> 8- Bromo -10- Phenylindolo [3,2,1-kl] phenothiazine &lt; RTI ID = 0.0 &gt;  synthesis

Phenylindolo [3,2,1-kl] phenothiazine (71.5 g, 204.7 mmol), NBS (36.4 g, 204.7 mmol) and methylene chloride (1000 ml) were added dropwise at 0 ° C under a nitrogen stream, Lt; / RTI &gt; for 12 hours.

After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography (Hexane: EA = 6: 1 (v / v)) to remove moisture with MgSO ₄ , to obtain 8-bromo- , 2,1-kl] phenothiazine (64.0 g, yield 73%).

^{1 H-NMR: δ 6.91 (} d, 1H), 6.97 (d, 1H), 7.19 (t, 1H), 7.41-7.53 (m, 6H), 7.75-7.77 (m, 3H), 7.89 (s, 1H ), 7.99 (d, 1 H)

Step 4: Synthesis of 10-phenyl-8- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) indolo [3,2,1-kl] Synthesis of thiazine

Phenylthio [3,2,1-kl] phenothiazine (64.0 g, 149.5 mmol), 4,4,4 ', 4', 5,5,5 ' Dioxaborolane) (41.8 g, 164.4 mmol), Pd (dppf) Cl ₂ (13.1 g, 15.0 mmol), KOAc (42.2 g, 448.4 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130 ° 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 purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain 10- , 5-tetramethyl-1,3,2-dioxabororan-2-yl) indolo [3,2,1-kl] phenothiazine (53.3 g, yield 75%).

¹ H-NMR:? 1.20 (s, 12H), 7.19-7.21 (m, 2H), 7.41-7.53 (m, 7H), 7.75-7.77 , 1H)

<Step 5> Synthesis of 8- (2- Nitrophenyl ) -10- Phenylindolo [3,2,1-kl] phenothiazine &lt; RTI ID = 0.0 &gt;  synthesis

Phenyl] -8- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) indolo [3,2,1-kl] phenothiazine triazine (53.3 g, 112.1 mmol), 1- bromo-2-nitrobenzene (27.2 g, 134.5 mmol), Pd (PPh 3) 4 (6.5 g, 5.6 mmol), K 2 CO 3 (31.0 g, 224.2 mmol) and 1,4-dioxane / H ₂ O (500 ml / 100 ml) 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 resulting organic layer and then purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain 8- (2-nitrophenyl) Phenothiazine (33.8 g, yield 64%).

^{1 H-NMR: δ 7.19-7.21 (} m, 2H), 7.41-7.53 (m, 6H), 7.72-7.77 (m, 4H), 7.89 (m, 2H), 7.99-8.03 (m, 4H)

<Step 6> IPT Synthesis of -4

Phenothiazine (33.8 g, 71.7 mmol), triphenylphosphine (47.0 g, 179.4 mmol), and 1 (2-nitrophenyl) , And 2-dichlorobenzene (500 ml) were added thereto, followed by stirring 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 purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain IPT-4 (18.6 g, yield 59%).

The ^{IPT-4 1 H-NMR:} δ 7.02 (s, 1H), 7.19-7.20 (m, 2H), 7.41-7.53 (m, 7H), 7.63 (d, 1H), 7.75-7.77 (m, 3H) , 7.89 (d, IH), 7.99 (d, IH), 8.19

[ Preparation Example  5] IPT Synthesis of -5

<Step 1> Synthesis of 10- (2- Bromophenyl ) -10H- Of phenox  synthesis

In a nitrogen atmosphere 10H- phenoxazine (100 g, 545.8 mmol), 1- bromo-2-iodobenzene (185.3 g, 655.0 mmol), Cu (17.3 g, 272.9 mmol), K 2 CO 3 (150.9 g, 1091.6 mmol) and nitrobenzene (2000 ml) were mixed and stirred at 210 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to remove moisture with MgSO _4. 10- (2- Phenoxyphthalate (118.1 g, yield 64%).

^{1 H-NMR: δ 6.96-7.23 (} m, 11H), 7.66 (d, 1H)

<Step 2> Indolo [3,2,1-kl] phenoxazine  synthesis

(118.1 g, 349.3 mmol), Pd (OAc) ₂ (7.84 g, 34.9 mmol), PCy ₃ HBF ₄ (25.7 g, 69.9 mmol), K 2 CO 3 (96.6 g, 698.7 mmol) and DMA (1500 ml) were mixed and stirred at 170 占 폚 for 3 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 give indolo [3,2,1-kl] phenoxazine (81.8 g, yield 91% .

^{1 H-NMR: δ 6.77 (} d, 1H), 7.14-7.21 (m, 3H), 7.31 (t, 1H), 7.42 (t, 1H), 7.50-7.58 (m, 2H), 7.69 (d, 1H ), 8.19 (d, 1 H), 8.27 (d, 1 H)

<Step 3> 8- Bromoindolo [3,2,1-kl] phenoxazine  synthesis

(81.8 g, 317.9 mmol), NBS (56.6 g, 317.9 mmol) and methylene chloride (1000 ml) were added dropwise at 0 占 폚 under a nitrogen stream and the mixture was stirred at room temperature for 12 hours Lt; / RTI &gt;

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 = 6: 1 (v / v)) to obtain 8-bromoindolo [ (90.8 g, yield 85%).

^{1 H-NMR: δ 6.66 (} d, 1H), 7.13-7.14 (m, 2H), 7.20 (t, 1H), 7.31 (t, 1H), 7.42 (t, 1H), 7.50-7.58 (m, 2H ), 7.69 (d, 1 H), 8.19 (d, 1 H)

<Step 4> Synthesis of 8- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) indolo [3,2,1-kl]

(90.8 g, 270.2 mmol), 4,4,4 ', 4', 5,5,5 &apos;,5'-octamethyl (75.7 g, 297.2 mmol), Pd (dppf) Cl ₂ (23.7 g, 27.0 mmol), KOAc (76.3 g, 810.6 mmol) And 1,4-dioxane (1000 ml) were mixed and stirred at 130 ° C for 12 hours.

After the reaction was completed, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to remove moisture with MgSO ₄ . Methyl-1,3,2-dioxabororen-2-yl) indolo [3,2,1-kl] phenoxazine (83.9 g, yield 81%).

^{1 H-NMR: δ 1.20 (} s, 12H), 6.77 (d, 1H), 7.14-7.20 (m, 2H), 7.31-7.50 (m, 4H), 7.58 (d, 1H), 7.69 (d, 1H ), 8.19 (d, 1 H)

&Lt; Step 5 > 8- (2-nitrophenyl) indolo [3,2,1-kl] phenoxazine  synthesis

(3, 1, 1-kl) phenoxyran (83.9 g, 0.35 mmol) was added to a solution of 8- (4,4,5,5-tetramethyl-1,3,2-dioxabororen- 218.9 mmol), 1- bromo-2-nitrobenzene (53.1 g, 262.6 mmol), Pd (PPh 3) 4 (12.6 g, 10.9 mmol), K 2 CO 3 (60.5 g, 437.7 mmol) and 1,4-dioxane / H ₂ O (500 ml / 100 ml) 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 the residue was purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to obtain 8- (2-nitrophenyl) indolo [3,2,1- g, yield 78%).

^{1 H-NMR: δ 6.96 (} d, 1H), 7.14-7.20 (m, 2H), 7.31 (t, 1H), 7.42 (t, 1H), 7.50-7.58 (m, 2H), 7.69-7.72 (m , 2H), 7.89 (t, 1H), 8.00-8.03 (m, 2H), 8.18-8.19

<Step 6> IPT Synthesis of -5

(64.6 g, 170.7 mmol), triphenylphosphine (111.9 g, 426.8 mmol), and 1,2-dichlorobenzene were added to a solution of 8- (2-nitrophenyl) indolo [ (500 ml) was added thereto, followed by stirring 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 purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain IPT-5 (42.6 g, yield 72%).

The ^{IPT-5 1 H-NMR:} δ 6.74 (s, 1H), 7.14-7.20 (m, 3H), 7.31-7.50 (m, 4H), 7.58 (d, 1H), 7.63-7.69 (m, 2H) , 8.19-8.20 (m, 2H), 8.26 (b, IH)

[ Preparation Example  6] IPT - 6 of  synthesis

<Step 1> Synthesis of 10- (2- Bromophenyl ) -9,9-dimethyl-9,10- Dihydroacridine  synthesis

(100 g, 477.8 mmol), 1-bromo-2-iodobenzene (162.2 g, 573.3 mmol) and Cu (15.2 g, 238.9 mmol ), K ₂ CO ₃ (132.0 g, 955.6 mmol) and nitrobenzene (2000 ml) 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 = 10: 1 (v / v)) to obtain 10- (2- 9-dimethyl-9,10-dihydroacridine (101 g, yield 58%).

^{1 H-NMR: δ 1.69 (} s, 6H), 6.95 (m, 2H), 7.07 (d, 1H), 7.14-7.23 (m, 8H), 7.66 (d, 1H)

&Lt; Step 2 > 8,8-Dimethyl-8H- Indolo [3,2,1-de] acridine &lt; / RTI &gt;  synthesis

(101 g, 277.1 mmol), Pd (OAc) ₂ (6.22 g, 27.7 mmol), PCl (2-bromophenyl) -9,9-dimethyl-9,10-dihydroacridine ₃ HBF ₄ (20.4 g, 55.4 mmol), K 2 CO 3 (76.6 g, 554.2 mmol) and DMA (1500 ml) were mixed and stirred at 170 占 폚 for 3 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 8,8-dimethyl-8H-indolo [3,2,1- , Yield: 89%).

^{1 H-NMR: δ 1.69 (} s, 6H), 6.98 (d, 1H), 7.20-7.32 (m, 5H), 7.50 (t, 1H), 7.58-7.60 (m, 2H), 8.19 (d, 1H ), 8.45 (d, 1 H)

<Step 3> 5- Bromo -8,8-dimethyl-8H- Indolo [3,2,1-de] acridine &lt; / RTI &gt;  synthesis

(69.9 g, 246.6 mmol), NBS (43.9 g, 246.6 mmol) and methylene chloride (1000 ml) were added to a 0 Deg.] C and stirred at room temperature for 12 hours.

After completion of the reaction, 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 = 6: 1 (v / v)) to obtain 5-bromo-8,8- -Indolo [3,2,1-de] acridine (74.2 g, yield 83%).

^{1 H-NMR: δ 1.69 (} s, 6H), 6.87 (d, 1H), 7.16-7.32 (m, 5H), 7.50 (t, 1H), 7.58-7.60 (m, 2H), 8.19 (d, 1H )

Step 4 8,8-Dimethyl-5- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane -2-yl) -8H-indolo [3,2,1-de] acridine

8-dimethyl-8H-indolo [3,2,1-de] acridine (74.2 g, 204.7 mmol), 4,4,4 ' (57.2 g, 225.2 mmol), Pd (dppf) Cl ₂ (17.9 g, 20.5 mmol), and the like were added to a solution of 5,5 ', 5'-octamethyl-2,2'- ), KOAc (57.8 g, 614.1 mmol) and 1,4-dioxane (1000 ml) were mixed and stirred at 130 ° C for 12 hours.

After completion of the reaction, 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 obtain 8,8- , 5,5-tetramethyl-1,3,2-dioxabororen-2-yl) -8H-indolo [3,2,1-de] acridine (70.4 g, yield 84% .

^{1 H-NMR: δ 1.20 (} s, 12H), 1.69 (s, 6H), 7.20-7.32 (m, 4H), 7.39-7.40 (m, 2H), 7.50 (t, 1H), 7.58-7.60 (m , &Lt; / RTI &gt; 2H), 8.19 (d, 1H)

Step 5 8,8-Dimethyl-5- (2- Nitrophenyl ) -8H- Indolo [3,2,1-de] acridine &lt; / RTI &gt;  synthesis

Dimethyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -8H-indolo [3,2,1 -de] acridine (70.4 g, 172 mmol), 1- bromo-2-nitrobenzene (41.7 g, 206.4 mmol), Pd (PPh 3) 4 (9.9 g, 8.6 mmol), K 2 CO 3 (47.5 g, 343.9 mmol) and 1,4-dioxane / H ₂ O (500 ml / 100 ml) 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 = 5: 1 (v / v)) to obtain 8,8-dimethyl-5- (2-nitrophenyl) -8H- , 1-de] acridine (57.0 g, yield 82%).

^{1 H-NMR: δ 1.69 (} s, 6H), 7.17-7.32 (m, 5H), 7.50 (t, 1H), 7.58-7.60 (m, 2H), 7.72 (t, 1H), 7.89 (t, 1H ), 8.00-8.03 (m, 2H), 8.19-8.24 (m, 2H)

<Step 6> IPT Synthesis of -6

8H-indolo [3,2,1-de] acridine (57.0 g, 141 mmol) and triphenylphosphine (92.5 g, 353.5 mmol) and 1,2-dichlorobenzene (500 ml) were added thereto, followed by stirring 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 purified by column chromatography (Hexane: MC = 4: 1 (v / v)) to obtain IPT-6 (36.2 g, yield 69%).

¹ of the IPT-6 H-NMR: δ 1.69 (s, 6H), 7.20-7.32 (m, 5H), 7.50-7.63 (m, 6H), 8.19 (m, 2H), 8.21 (b, 1H)

[ Synthetic example  1] Synthesis of A-1

IPT-1 (2.4 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 purified by column chromatography to obtain the target compound A-1 (2.9 g, yield 65%).

Mass (calc .: 669.8, found: 669 g / mol)

[ Synthetic example  2] Synthesis of A-2

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- -4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound A-2 , Yield: 63%).

Mass (theory: 683.79, found: 683 g / mol)

[ Synthetic example  3] Synthesis of A-3

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 3-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound A-3 , Yield: 72%).

Mass (theory: 683.79, found: 683 g / mol)

[ Synthetic example  4] Synthesis of A-4

IPT-1 (2.4 g, 6.7 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) 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 xylene (25 ml) were mixed and stirred at 1401 캜 for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound A-4 (3.7 g, yield 75%).

Mass (theory: 745.9, measurement: 745 g / mol)

[ Synthetic example  5] Synthesis of A-5

2- (3 &quot; -chloro- [1, 1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- (4 g, 8.0 mmol) was used as the starting material, 1 ': 3', 1 "-terphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Example 4 was repeated to obtain the target compound A-5 (3.9 g, yield 70%).

Mass (theory: 822.00, measurement: 822 g / mol)

[ Synthetic example  6] Synthesis of A-6

Instead of 3-bromo-1,1'-bis (3'-chloro- [1,1'-biphenyl] The procedure of Synthetic Example 4 was repeated except that phenyl (1.9 g, 8.0 mmol) was used to obtain the target compound A-6 (2.4 g, yield 69%).

Mass (theory: 514.64, measurement: 514 g / mol)

[ Synthetic example  7] Synthesis of A-7

Instead of 2-chloro-4-phenylquinazoline (1.9 ' -biphenyl-3-yl) g, 8.0 mmol), the target compound A-7 (2.4 g, yield 63%) was obtained.

Mass (theory: 566.68, measurement: 566 g / mol)

[ Synthetic example  8] Synthesis of A-8

4 - ([1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- (2.9 g, yield 68%) was obtained by carrying out the same procedure as in Synthesis Example 4, except for using 2-chloro-4- .

Mass (theory: 642.78, measurement: 642 g / mol)

[ Synthetic example  9] Synthesis of B-1

IPT-2 (2.8 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 purified by column chromatography to obtain the target compound B-1 (3.3 g, yield 68%).

Mass (theory: 719.86, measurement: 719 g / mol)

[ Synthetic example  10] Synthesis of B-2

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound B-2 , Yield: 70%).

Mass (theory: 733.85, found: 733 g / mol)

[ Synthetic example  11] Synthesis of B-3

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 3-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound B-3 , Yield: 63%).

Mass (theory: 733.85, found: 733 g / mol)

[ Synthetic example  12] Synthesis of B-4

IPT-2 (2.8 g, 6.7 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) 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 xylene (25 ml) were mixed and stirred at 1401 캜 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 (3.8 g, yield 72%).

Mass (theory: 795.96, measured: 795 g / mol)

[ Synthetic example  13] Synthesis of B-5

2- (3 &quot; -chloro- [1, 1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- (4 g, 8.0 mmol) was used as the starting material, 1 ': 3', 1 "-terphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Example 12 was repeated to obtain the target compound B-5 (3.6 g, yield 62%).

Mass (theory: 872.06, measurement: 872 g / mol)

[ Synthetic example  14] Synthesis of B-6

Instead of 3-bromo-1,1'-bis (3'-chloro- [1,1'-biphenyl] (2.5 g, yield 67%) was obtained by carrying out the same procedure as in Synthesis Example 12, except that phenyl (1.9 g, 8.0 mmol) was used.

Mass (theory: 564.7, measured: 564 g / mol)

[ Synthetic example  15] Synthesis of B-7

Instead of 2-chloro-4-phenylquinazoline (1.9 ' -biphenyl-3-yl) g, 8.0 mmol), the target compound B-7 (2.7 g, yield 65%) was obtained.

Mass (theory: 616.74, measured: 616 g / mol)

[ Synthetic example  16] Synthesis of B-8

4 - ([1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- (3.3 g, yield 71%) was obtained by carrying out the same processes as in Synthesis Example 12, except for using 2-chloro-4- .

Mass (theory: 692.84, measured: 692 g / mol)

[ Synthetic example  17] Synthesis of C-1

IPT-3 (2.9 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 purified by column chromatography to obtain the target compound C-1 (3.2 g, yield 65%).

Mass (theory: 745.9, measurement: 745 g / mol)

[ Synthetic example  18] Synthesis of C-2

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound C- , Yield: 63%).

Mass (theory: 759.89, measurement: 759 g / mol)

[ Synthetic example  19] Synthesis of C-3

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 3-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound C-3 , Yield: 68%).

Mass (theory: 759.89, measurement: 759 g / mol)

[ Synthetic example  20] Synthesis of C-4

IPT-3 (2.9 g, 6.7 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) 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 xylene (25 ml) were mixed and stirred at 1401 캜 for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound C-4 (3.4 g, yield 61%).

Mass (theory: 822, measurement: 822 g / mol)

[ Synthetic example  21] Synthesis of C-5

2- (3 &quot; -chloro- [1, 1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- (4 g, 8.0 mmol) was used as the starting material, 1 ': 3', 1 "-terphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Example 20 was repeated to obtain the target compound C-5 (3.9 g, yield 64%).

Mass (theory: 898.1, measurement: 898 g / mol)

[ Synthetic example  22] Synthesis of C-6

Instead of 3-bromo-1,1'-bis (3'-chloro- [1,1'-biphenyl] (2.4 g, yield: 61%) was obtained by carrying out the same procedure as in Synthesis Example 20, except that phenyl (1.9 g, 8.0 mmol) was used.

Mass (theory: 590.74, measured: 590 g / mol)

[ Synthetic example  23] Synthesis of C-7

Instead of 2-chloro-4-phenylquinazoline (1.9 ' -biphenyl-3-yl) g, 8.0 mmol), the target compound C-7 (3.0 g, yield 69%) was obtained.

Mass (theory: 642.78, measurement: 642 g / mol)

[ Synthetic example  24] Synthesis of C-8

4 - ([1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- (3.2 g, yield 66%) was obtained by carrying out the same processes as in Synthesis Example 20, except for using 2-chloro-4- .

Mass (theory: 718.88, measurement: 718 g / mol)

[ Synthetic example  25] Synthesis of D-1

IPT-4 (2.9 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 purified by column chromatography to obtain the target compound D-1 (3.5 g, yield 71%).

Mass (theory: 745.9, measurement: 745 g / mol)

[ Synthetic example  26] Synthesis of D-2

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of D- , Yield: 72%).

Mass (theory: 759.89, measurement: 759 g / mol)

[ Synthetic example  27] Synthesis of D-3

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 3-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of D- , Yield: 70%).

Mass (theory: 759.89, measurement: 759 g / mol)

[ Synthetic example  28] Synthesis of D-4

IPT-4 (2.9 g, 6.7 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) 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 xylene (25 ml) were mixed and stirred at 1401 캜 for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound D-4 (4.1 g, yield 74%).

Mass (theory: 822, measurement: 822 g / mol)

[ Synthetic example  29] Synthesis of D-5

2- (3 &quot; -chloro- [1, 1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- (4 g, 8.0 mmol) was used as the starting material, 1 ': 3', 1 "-terphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Example 28 was repeated to obtain the desired compound D-5 (3.9 g, yield 64%).

Mass (theory: 898.1, measurement: 898 g / mol)

[ Synthetic example  30] Synthesis of D-6

Instead of 3-bromo-1,1'-bis (3'-chloro- [1,1'-biphenyl] D-6 (2.9 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 28, except that phenyl (1.9 g, 8.0 mmol) was used.

Mass (theory: 590.74, measured: 590 g / mol)

[ Synthetic example  31] Synthesis of D-7

Instead of 2-chloro-4-phenylquinazoline (1.9 ' -biphenyl-3-yl) g, 8.0 mmol), the target compound D-7 (3.1 g, yield 71%) was obtained.

Mass (theory: 642.78, measurement: 642 g / mol)

[ Synthetic example  32] Synthesis of D-8

4 - ([1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- -4-yl) -2-chloroquinazoline (2.5 g, 8.0 mmol) was used in place of D-8 (3.4 g, yield 70%) .

Mass (theory: 718.88, measurement: 718 g / mol)

[ Synthetic example  33] Synthesis of E-1

IPT-5 (2.3 g, 6.7 mmol) and 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- 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 purified by column chromatography to obtain the target compound E-1 (2.8 g, yield 65%).

Mass (theory: 653.7, measurement: 653 g / mol)

[ Synthetic example  34] Synthesis of E-2

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound E-2 , Yield: 66%).

Mass (theory: 667.73, measurement: 667 g / mol)

[ Synthetic example  35] Synthesis of E-3

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 3-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound E-3 , Yield: 73%).

Mass (theory: 667.73, measurement: 667 g / mol)

[ Synthetic example  36] Synthesis of E-4

IPT-5 (2.3 g, 6.7 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) 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 xylene (25 ml) were mixed and stirred at 1401 캜 for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound E-4 (3.7 g, yield 75%).

Mass (theory: 729.84, measurement: 729 g / mol)

[ Synthetic example  37] Synthesis of E-5

2- (3 &quot; -chloro- [1, 1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- (4 g, 8.0 mmol) was used as the starting material, 1 ': 3', 1 "-terphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Example 36 was repeated to obtain the target compound E-5 (3.8 g, yield 71%).

Mass (theory: 805.94, measurement: 805 g / mol)

[ Synthetic example  38] Synthesis of E-6

Instead of 3-bromo-1,1'-bis (3'-chloro- [1,1'-biphenyl] (2.3 g, yield 70%) was obtained by carrying out the same procedure as in Synthesis Example 36, except that phenyl (1.9 g, 8.0 mmol) was used.

Mass (theory: 498.58, found: 498 g / mol)

[ Synthetic example  39] Synthesis of E-7

Instead of 2-chloro-4-phenylquinazoline (1.9 ' -biphenyl-3-yl) g, 8.0 mmol), the target compound E-7 (2.3 g, yield 63%) was obtained.

Mass (theory: 550.62, measurement: 550 g / mol)

[ Synthetic example  40] Synthesis of E-8

4 - ([1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- (2.9 g, yield 68%) was obtained by carrying out the same processes as in Synthesis Example 36, except for using 2-chloro-4- .

Mass (theory: 626.72, measurement: 626 g / mol)

[ Synthetic example  41] Synthesis of F-1

IPT-6 (2.5 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 purified by column chromatography to obtain the target compound F-1 (3.5 g, yield 76%).

Mass (theory: 679.82, measurement: 679 g / mol)

[ Synthetic example  42] Synthesis of F-2

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 4-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound F-2 , Yield: 71%).

Mass (theory: 693.81, measurement: 693 g / mol)

[ Synthetic example  43] Synthesis of F-3

Chloro-4- (dibenzo [b, d] furan-2-yl) -4-chloro- 3-yl) -6-phenyl-1,3,5-triazine (2.9 g, 8.0 mmol) was used in place of the target compound F-3 , Yield: 72%).

Mass (theory: 693.81, measurement: 693 g / mol)

[ Synthetic example  44] Synthesis of F-4

IPT-6 (2.5 g, 6.7 mmol) and 2- (3'-chloro- [1,1'-biphenyl] -3-yl) 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 xylene (25 ml) were mixed and stirred at 1401 캜 for 3 hours. After completion of the reaction, the solid salt was filtered and purified by column chromatography to obtain the target compound F-4 (3.5 g, yield 70%).

Mass (theory: 755.92, measurement: 755 g / mol)

[ Synthetic example  45] Synthesis of F-5

2- (3 &quot; -chloro- [1, 1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5- (4 g, 8.0 mmol) was used as the starting material, 1 ': 3', 1 "-terphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine The procedure of Example 44 was followed to obtain the target compound F-5 (3.9 g, yield 70%).

Mass (theory: 832.02, measurement: 832 g / mol)

[ Synthetic example  46] Synthesis of F-6

Instead of 3-bromo-1,1'-bis (3'-chloro- [1,1'-biphenyl] (2.6 g, yield 73%) was obtained by carrying out the same procedure as in Synthesis Example 44, except that phenyl (1.9 g, 8.0 mmol) was used.

Mass (theory: 524.66, measurement: 524 g / mol)

[ Synthetic example  47] Synthesis of F-7

Instead of 2-chloro-4-phenylquinazoline (1.9 ' -biphenyl-3-yl) g, 8.0 mmol), the target compound F-7 (2.9 g, yield 75%) was obtained.

Mass (theory: 576.7, measurement: 576 g / mol)

[ Synthetic example  48] Synthesis of F-8

4 - ([1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3'- (3.1 g, yield 71%) was obtained by carrying out the same procedure as in Synthesis Example 44, except that 2-chloro-4- .

Mass (theory: 652.8, measured: 652 g / mol)

[ Example  1 to 30] green organic Field  Fabrication of light emitting device

The compounds synthesized in Synthesis Examples 1 to 48 were subjected to high purity sublimation purification by a conventionally known method, and then 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.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent electrode + host compound + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP and BCP are as follows.

[ 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 the compound A-1 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  One]

Current efficiency and emission peak at a current density (10) mA / cm &lt; 2 &gt; were measured for each of the green organic electroluminescent devices manufactured in Examples 1 to 30 and Comparative Example 1, Respectively.

Sample Host Driving voltage EL peak Current efficiency (V) (nm) (cd / A) Example 1 A-1 6.65 518 41.3 Example 2 A-2 6.65 515 41.2 Example 3 A-3 6.77 518 41.3 Example 4 A-4 6.66 518 41.3 Example 5 A-5 6.66 518 41.2 Example 6 B-1 6.51 517 38.9 Example 7 B-2 6.77 515 41.3 Example 8 B-3 6.7 515 41.3 Example 9 B-4 6.77 515 41.3 Example 10 B-5 6.7 515 41.2 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 6.51 515 41.3 Example 24 E-4 6.7 518 41.2 Example 25 E-5 6.7 518 41.3 Example 26 F-1 6.51 517 41.3 Example 27 F-2 6.77 515 41.2 Example 28 F-3 6.7 515 38.9 Example 29 F-4 6.51 515 41.3 Example 30 F-5 6.77 515 42 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound according to the present invention was used in the light emitting layer of a green organic electroluminescent device (Examples 1 to 30), compared with the case where the conventional CBP was used for the green organic electroluminescent device (Comparative Example 1) It was confirmed that the efficiency and the driving voltage were excellent.

[ Example  31 to 42] Red organic Field  Fabrication of light emitting device

The compound thus synthesized was subjected to high purity sublimation purification by a conventionally known method, and 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.

M-MTDATA (60 nm) / TCTA (80 nm) / 90% on the prepared ITO transparent electrode + 10% (piq) ₂ Ir (acac) (300 nm) / BCP ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Comparative Example  2] Red organic Field  Fabrication of light emitting device

A red organic electroluminescent device was fabricated in the same manner as in Example 31 except that CBP was used instead of the compound A-7 of Synthesis Example 7 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 31 to 42 and Comparative Example 2 are as follows.

[ Evaluation example  2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 31 to 42 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host Driving voltage Current efficiency (V) (cd / A) Example 31 A-7 4.41 15.2 Example 32 A-8 4.31 13.4 Example 33 B-7 4.62 10.6 Example 34 B-8 4.63 10.7 Example 35 C-7 4.81 12.1 Example 36 C-8 4.81 10.8 Example 37 D-7 4.64 13.2 Example 38 D-8 4.64 11.9 Example 39 E-7 4.53 11.5 Example 40 E-8 4.55 12.3 Example 41 F-7 4.64 11.9 Example 42 F-8 4.87 12.5 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention was used for the light emitting layer of the red organic electroluminescent device (Examples 31 to 42), the efficiency of the conventional CBP was higher than that of the red organic electroluminescent device (Comparative Example 2) And the driving voltage were excellent.

[ Example  43 to 48] Organic Field  Fabrication of light emitting device

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, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes And the substrate was transferred to the back vacuum deposition machine.

 (60 nm) / compound of Table 3 (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) on the ITO transparent electrode prepared above ) / Al (200 nm).

The structures of m-MTDATA, TCTA, CBP, Ir (ppy) ₃ and BCP are as follows. DS-H522 and DS-501 used in the device fabrication are products of Doosan Electronics BG.

[ Comparative Example  3] abandonment Field  Fabrication of light emitting device

An organic electroluminescent device was prepared in the same manner as in Example 43, except that NPB was used as the hole transport layer material instead of the compound A-6 used as the hole transport layer material in forming the hole transport layer in Example 43. The structure of the NPB used is as follows.

[ Evaluation example  3]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 43 to 48 and Comparative Example 3, respectively, and the results are shown in Table 3 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 43 A-6 4.8 19.4 Example 44 B-6 5.1 20 Example 45 C-6 4.8 19.2 Example 46 D-6 5.1 21.1 Example 47 E-6 5.1 19.2 Example 48 F-6 5.1 21.1 Comparative Example 3 NPB 5.2 18.1

As shown in Table 3, the organic electroluminescent device using the compounds (A-6 to F-6) according to the present invention as the hole transport layer (Examples 43 to 48) The comparative example 3) exhibits better current efficiency and better driving voltage.

[ Example  49 to 78] Blue organic Field  Fabrication of light emitting device

Compound A-1 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was produced 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.

(5 nm) / Alq3 (25 nm) / LiF (30 nm) on the ITO transparent electrode prepared above, DS-205 (80 nm) / NPB (15 nm) / AND + 5% DS- (1 nm) / Al (200 nm) in this order to form an organic electroluminescent device.

The structures of NPB, AND and Alq ₃ used in this case are as follows.

[ Comparative Example  4] Blue organic Field  Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 49 except that the lifetime improvement layer was not included and Alq ₃ , which is an electron transporting layer material, was deposited at 30 nm instead of 25 nm.

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

An organic electroluminescent device was fabricated in the same manner as in Example 49 except that BCP was used instead of Compound A-1 used as the lifetime improving layer material in Example 49.

The structure of the BCP used is as follows.

[ Evaluation example  4]

The driving voltage, current efficiency, light emission wavelength and lifetime (T97) at a current density of 10 mA / cm 2 were measured for the organic electroluminescent devices prepared in Examples 49 to 78 and Comparative Examples 4 and 5, respectively, Are shown in Table 4 below.

Sample Life improvement layer Driving voltage Current efficiency EL peak life span (V) (cd / A) (nm) (hr, T ₉₇ ) Example 49 A-1 4.3 6.2 463 32 Example 50 A-2 5.3 6.1 462 39 Example 51 A-3 5.3 6.1 463 45 Example 52 A-4 5.1 6.0 459 45 Example 53 A-5 5.2 6.0 459 39 Example 54 B-1 5.2 6.0 459 38 Example 55 B-2 4.3 6.0 459 37 Example 56 B-3 4.3 6.0 459 39 Example 57 B-4 5.3 5.9 451 44 Example 58 B-5 5.1 6.3 459 43 Example 59 C-1 5.3 5.9 459 48 Example 60 C-2 5.2 6.2 459 49 Example 61 C-3 5.0 6.1 459 41 Example 62 C-4 4.8 6.1 462 39 Example 63 C-5 5.1 6.0 463 44 Example 64 D-1 5.0 6.0 460 43 Example 65 D-2 4.8 6.0 459 48 Example 66 D-3 5.0 6.0 459 49 Example 67 D-4 5.3 6.0 459 41 Example 68 D-5 5.3 5.9 459 42 Example 69 E-1 5.2 6.2 451 47 Example 70 E-2 4.3 6.1 459 43 Example 71 E-3 4.3 6.1 451 48 Example 72 E-4 5.3 6.0 469 43 Example 73 E-5 5.1 6.0 461 48 Example 74 F-1 5.3 6.0 461 49 Example 75 F-2 5.2 6.0 459 41 Example 76 F-3 5.0 6.2 451 42 Example 77 F-4 4.8 6.1 469 47 Example 78 F-5 5.1 6.0 461 44 Comparative Example 4 - 4.8 6.0 461 49 Comparative Example 5 BCP 5.3 5.9 458 28

As can be seen from Table 4, in the case of the blue organic electroluminescent device using the compounds A-1 to F-5 according to the present invention as the lifetime improving layer materials (Examples 49 to 78) (Comparative Example 4), which is similar to or slightly superior to the blue organic electroluminescent device (Comparative Example 4). However, the current efficiency and lifetime were greatly improved.

In addition, in the case of the blue organic electroluminescent device using the compounds A-1 to F-5 according to the present invention as the lifetime improving layer materials (Examples 49 to 78), the blue- Compared with the organic electroluminescent device (Comparative Example 5), the driving voltage and the current efficiency were excellent, and the service life was remarkably improved.

[ Example  79 to 90] Blue organic Field  Fabrication of light emitting device

Compound A-1 synthesized in Synthesis Example 1 was subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was produced 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.

(30 nm) / LiF (1 nm) / Al (30 nm) / 5% DS-405 (30 nm) on the ITO transparent electrode prepared as described above. 200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Evaluation example  5]

The driving voltage, current efficiency, light emission wavelength and lifetime (T97) at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 79 to 90 and Comparative Example 4, respectively, Table 5 shows the results.

Sample Electron transport layer Driving voltage Current efficiency Emission peak (V) (cd / A) (nm) Example 79 A-1 4.5 5.8 457 Example 80 A-4 4.7 5.8 463 Example 81 B-1 4.5 5.8 460 Example 82 B-4 4.2 6 457 Example 83 C-1 4.5 5.8 463 Example 84 C-4 4.7 5.8 457 Example 85 D-1 4.5 5.8 463 Example 86 D-4 4.2 5.8 457 Example 87 E-1 4.5 5.8 463 Example 88 E-4 4.2 5.8 461 Example 89 F-1 4.5 5.8 463 Example 90 F-4 4.2 5.8 461 Comparative Example 4 _ 4.7 5.6 458

As can be seen from Table 5, in the case of the blue organic electroluminescent device using the compounds A-1 to F-4 according to the present invention as the electron transporting layer materials (Examples 79 to 90), Alq ₃ was used as the electron transporting layer The driving voltage and the current efficiency were further improved as compared with the blue organic electroluminescent device (Comparative Example 4).

As described above, it was confirmed that when the compound according to the present invention is used as a material for improving the lifetime and an electron transporting layer material, the driving voltage and the current efficiency can be improved and the lifetime characteristics can be greatly improved.

10: anode 20: cathode
30: organic layer 31: hole transport layer
32: light emitting layer 33: hole transporting auxiliary layer
34: Electron transport layer 35: Electron transport layer
36: electron injection layer 37: hole injection layer

Claims (16)

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

In Formula 1,
R ₁ to R ₁₂ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ of 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 ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ alkyl sulfonyl group, aryl sulfonyl group of a _{C 6 ~ C 60, C 1} ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group, C ₁ ~ C ₄₀ alkyl carbonyl group, C ₆ ~ C ₆₀ aryl carbonyl group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or of the number two substituents nuclear atoms bonded to each other to from 5 to 50 aromatic ring, nucleus atom adjacent 5 To 50 non-aromatic condensed polycyclic, An aromatic heterocycle having 5 to 50 nuclear atoms, or a non-aromatic condensed heterocyclic ring having 5 to 50 nuclear atoms;
m and n are each independently an integer of 0 to 2;
L ₁ and L ₂ are each independently a C ₆ to C ₁₈ arylene group or a heteroarylene group having 5 to 18 nucleus atoms and when a plurality of each of L ₁ and L ₂ are the same or different from each other;
X ₁ is O, S, Se, N (Ar ₂ ), C (Ar ₃ ) (Ar ₄ ) and Si (Ar ₅ ) (Ar ₆ );
Ar ₁ to Ar ₆ each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, 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 ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C aryl silyl group of _60, C ₁ ~ C ₄₀ alkyl sulfonyl group, aryl sulfonyl group of a _{C 6 ~ C 60, C 1} ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group, C ₁ ~ C ₄₀ alkyl carbonyl A C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylamine group;
The aryl group and heteroarylene group of L ₁ and L ₂ and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, and alkyloxy group of R ₁ to R ₁₂ and Ar ₁ to Ar ₆ An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, An aromatic ring, a non-aromatic condensed polycyclic aromatic heterocyclic ring, and a non-aromatic condensed heterocyclic ring formed by bonding a carbonyl group and an arylsilyl group with two adjacent substituents of R ₁ to R ₁₂ are each independently selected from deuterium, , A cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, An aryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkyl sulfonyl group of, C ₆ ~ C group of ₆₀ of the aryl sulfonyl group, C ₁ ~ C ₄₀ alkyl, boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group , A C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylsilyl group, and is substituted with a plurality of substituents They are the same as or different from each other. The method according to claim 1,
Each of R ₁ to R ₁₂ 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;
The alkyl, aryl and heteroaryl groups of R ₁ to R ₁₂ are each independently selected from the group consisting of 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. And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ , R ₇ and R ₈ , R ₉ and R ₁₀ , R ₁₀ and R ₁₁ and R ₁₁ and R &lt; ₁₂ &gt; each independently combine with a ring represented by the following formula (2) to form a condensed ring:
(2)

In Formula 2,
The dotted line means a moiety in which the condensation is carried out in the above formula (1);
Z ₁ to Z ₄ are each independently N or C (Ar ₂ );
Ar ₂ 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 alkylsulfonyl group, a C ₆ to C ₆₀ arylsulfonyl group, a C ₁ to C ₄₀ alkylboron group , A C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphanyl group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, a C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ aryl carbonyl group and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of or, wherein the Ar ₂ is nuclear atoms two Ar ₂ are bonded to each other adjacent if multiple individuals from 5 to 50 aromatic ring, nucleus atoms Several 5 to 50 non-aromatic condensed polycyclic, An aromatic heterocycle having 5 to 50 nuclear atoms, or a non-aromatic condensed heterocyclic ring having 5 to 50 nucleus atoms, and a plurality of Ar _{2 s} may be the same as or different from each other;
Alkyl group of said Ar _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl sulfonyl group, aryl sulfonyl group, An aryloxy group, an arylboron group, an arylphosphonyl group, a mono- or diarylphosphinyl group, an alkylcarbonyl group, an arylcarbonyl group, and an arylsilyl group, an aromatic ring formed by bonding two adjacent Ar ₂ groups, Aromatic condensed polycyclic, aromatic heterocyclic and non-aromatic condensed heterocyclic ring are 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 C ₆ to C ₆₀ aryl groups, 5 to 60 heteroaryl groups, C ₆ to C ₆₀ aryloxy groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ An arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ alkylsulfonyl group, the aryl sulfonyl group of a _{C 6 ~ C 60, C 1} ~ C 40 group of an alkyl boron, C ₆ ~ aryl boronic of C _60, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group, C ₁ ~ C ₄₀ alkyl carbonyl, C of ₆ ~ C ₆₀ aryl carbonyl group and a C ₆ ~ aryl of C ₆₀ A silyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other. The method of claim 3,
Wherein each of Z ₁ to Z ₄ is independently C (Ar ₂ ), Ar ₂ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, alkynyl of C 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 _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 alkylsulfonyl group, a C _A C ₆ to C ₆₀ arylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphonyl group, a C ₆ to C ₆₀ mono or diaryl A phosphinoyl group, a C ₁ to C ₄₀ alkylcarbonyl group, a C ₆ to C ₆₀ arylcarbonyl group, and a C ₆ to C ₆₀ arylamine group;
Alkyl group of said Ar _2, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl sulfonyl group, aryl sulfonyl group, An arylcarbonyl group, an arylcarbonyl group and an arylsilyl group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, an aryloxy group, an aryloxy group, the alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, an aryloxy group of C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ of the , An alkyloxy group of C ₁ to C ₄₀ , an arylamine group of C ₆ to C ₆₀ , a cycloalkyl group of C ₃ to C ₄₀ , a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group , A C ₁ to C ₄₀ alkylsulfonyl group, a C ₆ to C ₆₀ arylsulfonyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ aryl A C ₆ -C ₆₀ mono or diarylphosphinyl group, a C ₁ -C ₄₀ alkylcarbonyl group, a C ₆ -C ₆₀ arylcarbonyl group, and a C ₆ -C ₆₀ arylsilyl group in the group consisting of And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein L ₁ and L ₂ are each independently a linker selected from the group consisting of the following formulas K-1 to K-4:

In the above formulas (K-1) to (K-4)
* Means the part where the combination is made. The method according to claim 1,
Wherein Ar ₁ is selected from the group consisting of 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;
The alkyl, aryl and heteroaryl groups of Ar ₁ are each independently substituted with at least one substituent selected from the group consisting of 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 And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 6,
Wherein Ar ₁ is a group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine , Pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, Benzothiophene, benzothienopyridine, and thienodipyridine; and the benzene ring may be optionally substituted with one or more substituents selected from the group consisting of:
Examples of the substituent of the above-mentioned Ar ₁ include methyl, ethyl, propyl, butyl, pentyl, hexyl, phenyl, biphenyl, terphenyl, , Dibenzofuran, benzofuran, benzothiophene, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine , Pyrazine, triazine, indole, benzimidazole, indazole, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, Benzothiopyrimidine, benzothienopyridine and thienodipyridine are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a nucleus A heteroaryl group having 5 to 60 atoms and substituted with at least one substituent selected from the group consisting of Or when they are unsubstituted or substituted with a plurality of substituents, they are the same or different from each other. The method according to claim 6,
Wherein Ar ₁ is a substituent represented by the following general formula (3) or (4):
(3)

[Chemical Formula 4]

In the above formulas (3) and (4)
* Denotes the part where the bond is made;
Z ₅ to Z ₉ are each independently N or C (Ar ₇ );
s is an integer from 0 to 4;
R ₄ is 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 alkynyl, C ₃ to C ₄₀ cycloalkyl, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, an aryloxy group of a C ₆ ~ C ₆₀ of, C _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 arylphosphonyl group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination group adjacent to form a condensed ring, when individual said R ₄ is a plurality, they are equal to each other Or different;
Ar ₇ 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 arylphosphate group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ selected from the group consisting of an aryl amine, or a, combination groups adjacent when forming a condensed ring, and individual said Ar ₇ is a plurality which the Are the same or different from each other;
Alkyl groups of the R ₄ and Ar _7, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of When they are substituted or unsubstituted with one or more substituents, and when they are substituted with a plurality of substituents, they are the same as or different from each other. 9. The method of claim 8,
Wherein the substituent represented by the general formula (3) is a substituent represented by the following general formula (5):
[Chemical Formula 5]

In Formula 5,
* Denotes the part where the bond is made;
R ₅ and R ₆ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, 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 ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, it said shed some light selected from the group consisting of an arylamine C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of;
Alkyl groups of the R ₅ and R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 When substituted with a plurality of substituents, they are the same as or different from each other;
Each of Z ₁ , Z ₃ and Z ₅ is as defined in claim 8. 9. The method of claim 8,
Wherein the substituent represented by the general formula (3) is a substituent represented by any one of the following formulas (L-1) to (L-3):

In the above formulas (L-1) to (L-3)
* Denotes the part where the bond is made,
R ₅ and R ₆ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, 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 ~ alkyloxy group of C _40, C ₆ ~ aryloxy group of C _60, C ₃ ~ C ₄₀ alkylsilyl group, C group ₆ ~ C ₆₀ aryl silyl, C ₁ ~ arylboronic of C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ group, C ₆ ~ for C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ is selected from the group consisting of an aryl amine of the C ₆₀ of the;
Alkyl groups of the R ₅ and R _6, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ alkyloxy group of C ₄₀ of, C ₆ ~ C ₆₀ arylamine group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₆₀ aryl group of boron, C ₆ ~ C ₆₀ aryl phosphazene group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of 1 And when they are substituted with a plurality of substituents, they are the same as or different from each other. 11. The method of claim 10,
Each of R ₅ and R ₆ is independently selected from the group consisting of 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;
The alkyl, aryl and heteroaryl groups of R ₅ and R ₆ are each independently selected from the group consisting of 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. And when they are substituted with a plurality of substituents, they are the same as or different from each other. 9. The method of claim 8,
Wherein the substituent represented by Formula 4 is a substituent represented by Formula 6:
[Chemical Formula 6]

In Formula 6,
* Denotes the part where the bond is made;
s, R &lt; ₄ &gt; and Ar &lt; ₇ &gt; are as defined in claim 8. 13. The method of claim 12,
Each of Ar ₇ and R ₄ is independently selected from the group consisting of 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;
The alkyl, aryl and heteroaryl groups of Ar ₇ and R ₄ are each independently selected from the group consisting of 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. And when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein said compound is selected from the group consisting of:

1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers 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 (1). 16. The method of claim 15,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron transporting auxiliary layer, an electron injecting layer, a lifetime improving layer, a light emitting layer and a light emitting auxiliary layer.

Images