KR20170076113A

KR20170076113A - Organic compounds and organic electro luminescence device comprising the same

Info

Publication number: KR20170076113A
Application number: KR1020150185971A
Authority: KR
Inventors: 최태진; 김동연
Original assignee: 주식회사 두산
Priority date: 2015-12-24
Filing date: 2015-12-24
Publication date: 2017-07-04
Also published as: KR101827067B1

Abstract

The present invention relates to a novel compound and an organic electroluminescent device including the same, and the compound according to the present invention is used for an organic material layer of an organic electroluminescent device, preferably a hole transporting layer or a light emitting auxiliary layer, , The driving voltage, the life and the like can be improved.

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,

X ₁ and X ₂ are each independently selected from the group consisting of O, S, N (R ₄ ) and C (R ₅ ) (R ₆ );

L ₁ to L ₃ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;

R ₁ and R ₄ to R ₆ are each independently 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 ~ 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, 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, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ tile to selected or adjacent from the group consisting of an aryl amine of the C ₆₀ combined to form a condensed ring, and , When a plurality of each of R ₄ to R ₆ is present, they are the same as or different from each other;

m and n are each independently an integer of 0 to 4;

R ₂ and R ₃ are each independently selected from deuterium, halogen, cyano group, 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 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 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 an aryl phosphine group, and groups binding to selected or adjacent from the group consisting of C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ with an aryl amine of the C ₆₀ to which they are attached may form a fused ring, wherein R ₂ and R ₃ are the same or different from each other;

Wherein L ₁ to the aryl group and a hetero arylene group, R ₁ to an alkyl group R ₆ in the L _3, 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 boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ 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 alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C _{6 0 &lt}; / RTI > arylsilyl group, and when they are substituted with a plurality of substituents, they may be the same or different.

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 .

"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.

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

"Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. 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 . &Lt; / 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.

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

"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.

"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. &Lt; / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

"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.

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

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.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

The organic compound according to the present invention is a structure in which a benzodisin moiety, a benzoxazine moiety, or a benzodioxin moiety is condensed with an indole to form a basic skeleton, and various substituents are bonded to or condensed with the basic skeleton. Characterized in that it is represented by the formula (1)

[Chemical Formula 1]

In Formula 1,

m and n are each independently an integer of 0 to 4;

In general, the phosphorescent light emitting layer among the organic material layers included in the organic electroluminescent device includes a host and a dopant to increase the color purity and increase the luminous efficiency. At this time, the host should have a triplet energy gap higher than the dopant. That is, the energy of the lowest excitation state of the host must be higher than the energy of the lowest emission state of the dopant in order to effectively provide phosphorescence from the dopant. In the case of the compound represented by Formula 1, the indole moiety has a broad singlet energy level and a high triplet energy level. When a specific substituent is introduced into a benzodisaphin moiety, a benzoxazine moiety or a benzodioxin moiety condensed with such an indole, the compound of the above formula (1) may be applied as a host of the light emitting layer to exhibit a higher energy level than the dopant have.

In addition, since the compound represented by Formula 1 has high triplet energy as described above, it is possible to prevent the exciton generated in the light emitting layer from diffusing (moving) to the adjacent electron transporting layer or hole transporting layer. Accordingly, an organic layer (hereinafter, referred to as a 'light emission-assisting layer') may be formed between the hole transporting layer and the light emitting layer using the compound of Formula 1 or an organic layer (hereinafter referred to as an 'electron transporting layer') may be formed between the light emitting layer and the electron transporting layer. ), Diffusion of the excitons is prevented by the compound. Thus, unlike the conventional organic electroluminescent devices not including the light-emission-assisting layer or the electron-transporting-assisting layer, the excitons substantially contributing to light emission in the light- The luminous efficiency of the device can be improved.

In addition, the compound represented by the formula (1) can control the energy level of HOMO and LUMO according to the substituent introduced into the basic skeleton, and can have a wide bandgap and a high carrier transporting property.

In addition, when the benzodioxin moiety is introduced, the compound of the present invention is capable of adsorbing a large amount of electron donating group (EDG) to the basic skeleton due to high hole transport ability of oxygen atoms, It can be easily used as a material. Further, when an electron withdrawing group (EWG) having a high electron absorbing property is bonded to the basic skeleton, the entire molecule has a bipolar characteristic, so that the bonding force between holes and electrons can be enhanced.

According to a preferred embodiment of the present invention, the compound represented by the formula (1) may be a compound represented by any one of the following formulas (2) to (7)

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 2 to 7,

m, n, R ₁ to R ₄ and L ₁ to L ₃ are as defined in the above formula (1).

According to a preferred embodiment of the present invention, each of L ₁ to L ₃ independently represents a linker represented by any one of the following formulas (8) to (13)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above Formulas 8 to 13,

* Denotes the part where the bond is made;

Y ₁ is O, S or N (R ₈ );

Y ₂ is O, S, N (R ₈ ) or C (R ₉ ) (R ₁₀ );

Y ₃ is N or C (R ₁₁ );

l is an integer from 0 to 4;

R ₇ is heavy hydrogen, 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 ₆ ~ C ₆₀ aryl group, the nucleus of atoms of A C ₆ to C ₆₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryloxy group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ heteroaryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphosphine groups, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ selected from the group consisting arylsilyl of C _60, or adjacent groups (e. g., L ₁ to L ₃ of any one or adjacent the other R _7, such as To form a condensed ring, and when a plurality of R < ₇ > s are present, they are the same as or different from each other;

R ₈ to R ₁₁ 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 ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ selected from the group consisting arylsilyl of C _60, or adjacent groups (e.g., any one of L ₁ to L ₃ Or the like) to form a condensed ring;

Alkyl group of the R ₇ to R _11, 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 substituted or unsubstituted aryl group, ~ 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 ~ arylamine group of C _60, 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 ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, 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 one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, R ₇ is a group consisting of deuterium, halogen, cyano group, C ₁ to C ₄₀ alkyl group, C ₆ to C ₆₀ aryl group and 5 to 60 nuclear heteroaryl groups &Lt; / RTI >

According to a preferred embodiment of the present invention, R ₁ is a substituent represented by any one of the following formulas (14) to (20)

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

In the above formulas 14 to 20,

* Means the part where the bond is made:

p and q are each independently an integer of 0 to 4;

Z ₁ to Z ₁₂ are each independently N or C (R ₁₄ );

Any one of Z ₁ to Z ₄ bonded to L ₃ in the above formulas 15 and 19 is C (R ₁₄ ), wherein R ₁₄ is a member;

T ₁ and T ₂ are each independently selected from the group consisting of a single bond, C (R ₁₅ ) (R ₁₆ ), N (R ₁₇ ), O and S, but not both T ₁ and T ₂ are single bonds;

R ₁₂ and R ₁₃ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of _{C 6 ~ C 60, C 1} ~ C 40 alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 C ₆ to C ₆₀ arylamino groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting arylsilyl of C ₆₀ of the adjacent group (e. g., L any one of ₁ to L _3, or Adjacent R ₁₂ or R ₁₃ ) to form a condensed ring, and when there are a plurality of R ₁₂ and R ₁₃ each, they are the same or different;

R ₁₄ to R ₁₇ each independently represent 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 ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ selected from the group consisting arylsilyl of C _60, or adjacent groups (e.g., any one of L ₁ to L ₃ Etc.) to form a condensed ring, and when there are a plurality of R ₁₄ to R ₁₇ each, they are the same or different from each other;

Alkyl group of said R ₁₂ to R _17, 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 substituted or unsubstituted aryl group, ~ 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 ~ arylamine group of C _60, 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 ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, 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 one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

The compound represented by the formula (1) of the present invention is a compound in which various substituents, especially an aryl group and / or a heteroaryl group, are introduced into the basic skeleton, whereby the molecular weight of the compound is significantly increased and the glass transition temperature is improved, (E. G., CBP). &Lt; / RTI > The compound represented by the formula (1) is also effective for inhibiting crystallization of the organic material layer.

Thus, the compound represented by the general formula (1) of the present invention can be used as an organic material layer of an organic electroluminescent device, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transporting / The performance and lifetime characteristics of the organic electroluminescent device can be greatly improved when the organic electroluminescent device is applied to an injection layer material, a light emitting auxiliary layer material, and a life improving layer material. Such an organic electroluminescent device can consequently maximize the performance of a full-color organic luminescent panel.

According to a preferred embodiment of the present invention, the substituents represented by the above formulas (14) to (20) may be substituents represented by any one of the following formulas A-1 to A-24,

In the above Formulas A-1 to A-24,

* Denotes the part where the bond is made,

t is an integer from 0 to 5;

l is an integer from 0 to 4;

v is an integer from 0 to 3;

u is an integer from 0 to 2;

R ₁₈ is heavy hydrogen, 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 ₆ ~ C ₆₀ aryl group, the nucleus of atoms of A C ₆ to C ₆₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryloxy group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ heteroaryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphosphine groups, C ₆ to mono- or diaryl phosphine of C ₆₀ blood group and a C ₆ and selected from the group consisting arylsilyl of C _60, or adjacent groups (e.g., any one of L ₁ to L _3, or adjacent to other R ₁₈ or that R ₁₄ to R _16, and the like) to form a condensed ring. When a plurality of R _{18 s} are present, they may be the same or different;

Alkyl group of the R _18, 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 boron group, 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 substituted or unsubstituted aryl group, 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 to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of When they are substituted or unsubstituted with a substituent and are substituted with a plurality of substituents, they may be the same or different,

R ₁₂ to R ₁₇ , p and q are as defined in the above formulas 14 to 20, respectively.

According to a preferred embodiment of the present invention, R ₁ is a substituent represented by the following general formula (21)

[Chemical Formula 21]

In Formula 21,

* Denotes the part where the bond is made;

R ₁₉ and R ₂₀ 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 ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ selected from the group consisting arylsilyl of C _60, or adjacent groups (e.g., any one of L ₁ to L ₃ , Or R ₁₉ and R ₂₀ may bond with each other to form a condensed ring;

Alkyl group of said R ₁₉ and R _20, 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 substituted or unsubstituted aryl group, ~ 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 ~ arylamine group of C _60, 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 ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, each of R ₁₉ and R ₂₀ 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 Can be selected from the group.

According to a preferred embodiment of the present invention, each of R ₁₉ and R ₂₀ is independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, phenyl, biphenyl, naphthalenyl, fluorenyl and carbazolyl &Lt; / RTI >

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

In the present invention, the compound represented by Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960), J. Chem. SOC. 4482 (1955) 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 > Preferably, the organic material layer containing the compound represented by Formula 1 may be an electron transporting auxiliary layer, a hole transporting layer, a light emitting layer, or a light emitting auxiliary layer.

According to an embodiment of the present invention, since the compound represented by the general formula (1) of the present invention has high triplet energy as described above, the exciton generated in the light emitting layer diffuses (moves) to the adjacent electron transporting layer or hole transporting layer, Can be prevented. Accordingly, when the light-emitting auxiliary layer is formed between the hole transporting layer and the light emitting layer or the electron transporting auxiliary layer is formed between the light emitting layer and the electron transporting layer using the compound of Formula 1, the diffusion of the excitons is prevented by the compound, Unlike a conventional organic electroluminescent device that does not include the light-emitting auxiliary layer or the electron transporting auxiliary layer, the number of the excitons contributing to light emission in the light emitting layer substantially increases, and the light emitting efficiency of the device can be improved.

In addition, according to an embodiment of the present invention, the compound represented by the formula (1) of the present invention has an electron donating group (EDG) bonded to the basic skeleton due to high hole transport ability of oxygen atoms in the benzodioxin moiety , It can be easily used as a hole transport layer material. In addition, when an electron attracting agent (EWG) having a high electron absorbing property is bonded to the basic skeleton, the whole molecule has a property of bipolarity, so that the binding force between holes and electrons can be enhanced.

According to an embodiment of the present invention, the light emitting layer of the organic electroluminescent device may include a host material, which may include a compound represented by the above formula (1) as a host material. Thus, when the compound represented by Formula 1 is incorporated as a light emitting layer material of an organic electroluminescent device, preferably a green phosphorescent host, the bonding strength between holes and electrons in the light emitting layer increases, Efficiency and power efficiency), lifetime, luminance and driving voltage, etc., can be improved.

The structure of the organic electroluminescent device according to the present invention is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially stacked. At this time, an electron transporting auxiliary layer may be further laminated between the light emitting layer and the electron transporting layer, and an electron injection layer may further be laminated on the electron transporting layer. In the present invention, at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron transporting assisting layer, and the electron injecting layer may include the compound represented by Formula 1, The light-emitting layer or the light-emission-assisting layer may include the compound represented by the above formula (1).

In addition, the structure of the organic electroluminescent device of the present invention may be a structure in which not only an anode, one or more organic compound layers and a cathode are sequentially laminated but also an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic compound layer.

The organic electroluminescent device of the present invention can be produced in the same manner as the organic electroluminescent device except that at least one or more of the organic material layers (for example, the electron transporting auxiliary layer, the hole transporting layer, the light emitting layer or the light emitting auxiliary layer) May be produced by forming other organic layers and electrodes using materials and methods known in the art.

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.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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 a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead 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.

[ Preparation Example 1] Compound Of Inv1 synthesis

<Step 1> 2- ( Benzo [b] [1,4] dithiene Yl) -4,4,5,5- Tetramethyl -1,3,2- Dioxaborolan synthesis

Bromobenzo [b] [1,4] dithi ne (93 g, 0.38 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- (115.8 g, 0.46 mol), Pd (dppf) Cl ₂ (31 g, 0.038 mol) and KOAc (111.9 g, 1.14 mol) were placed in a flask, Then, 1,4-dioxane (2 L) was added thereto and dissolved therein, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 2- (benzo [b] [1,4] dithi-2-yl) Tetramethyl-1,3,2-dioxaborolane (67 g, yield 60%).

&Lt; Step 2 > 2- (2-nitrophenyl) benzo [b] [1,4] dithiene synthesis

(Benzo [b] [1,4] dithi-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (obtained in Step 1 above) 2-nitrobenzene (57 g, 0.282 mol) and Pd (PPh ₃ ) ₄ (13.5 g, 0.011 mol) were placed in a flask and a 2M aqueous Na ₂ CO ₃ saturated solution 352 ml) and 1,4-dioxane (2 L) were added and dissolved, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 2- (2-nitrophenyl) benzo [b] [1,4] dithine (61 g, yield 92% .

&Lt; Step 3 > Of Inv1 synthesis

To a solution of 2- (2-nitrophenyl) benzo [b] [1,4] dithiene (61 g, 0.212 mol), triphenylphosphine (139 g, 0.53 mol), 1,2 -Dichlorobenzene (1 L) were mixed, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain Compound Inv1 (33 g, yield 60%).

[ Preparation Example 2] Compound Of Inv2 synthesis

<Step 1> 2- ( Benzo [b] [1,4] dioxin Yl) -4,4,5,5- Tetramethyl -1,3,2- Dioxaborolan synthesis

Bromo benzo [b] [1,4] dioxine (81 g, 0.38 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl- (115.8 g, 0.46 mol), Pd (dppf) Cl ₂ (31 g, 0.038 mol) and KOAc (111.9 g, 1.14 mol) were placed in a flask, Then, 1,4-dioxane (2 L) was added thereto and dissolved therein, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 2- (benzo [b] [1,4] dioxin-2-yl) Tetramethyl-1,3,2-dioxaborolane (61 g, yield 62%).

&Lt; Step 2 > 2- (2-nitrophenyl) benzo [b] [1,4] dioxine synthesis

(Benzo [b] [1,4] dioxin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (obtained in Step 1 above) Bromo-2-nitrobenzene (57 g, 0.282 mol) and Pd (PPh ₃ ) ₄ (13.5 g, 0.011 mol) were placed in a flask and a 2M aqueous Na ₂ CO ₃ saturated solution 352 ml) and 1,4-dioxane (2 L) were added and dissolved, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 2- (2-nitrophenyl) benzo [b] [1,4] dioxine (51 g, yield 86% .

&Lt; Step 3 > Of Inv2 synthesis

To a solution of 2- (2-nitrophenyl) benzo [b] [1,4] dioxine (51 g, 0.20 mol), triphenylphosphine (131 g, 0.5 mol), 1,2 -Dichlorobenzene (1 L) were mixed, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain Compound Inv2 (29 g, yield 65%).

[ Preparation Example 3] Compound Inv3 synthesis

&Lt; Step 1 > 3- Bromo -4-tosyl-4H- Benzo [b] [1,4] thiazine synthesis

Benzo [b] [1,4] thiazine (114 g, 0.50 mol) was added to KOH (280 g, 5.0 mol) in acetone (2 L). TsCl (105 g, 0.55 mol) was added and the mixture was refluxed for 3 hours and then cooled. Cold water (3 L) was poured while stirring. After stirring for 30 minutes, the crude product was obtained by filtration. After recrystallization from CH ₂ Cl ₂ / EtOH 3-bromo-4-tosyl-4H-benzo [b] [1,4] thiazine (145 g, yield 76%) was obtained.

&Lt; Step 2 > 3- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane Yl) -4-tosyl-4H- Benzo [b] [1,4] thiazine synthesis

Benzo [b] [1,4] thiazine (145 g, 0.38 mol), 4,4,4 ', 4', 5,5, (115.8 g, 0.46 mol), Pd (dppf) Cl ₂ (31 g, 0.038 mol) and KOAc (111.9 g, 1.14 mol) was placed in a flask, 1,4-dioxane (2 L) was added thereto, and the mixture was heated and stirred for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Yl) -4-tosyl-4H-benzo [b] [1,4] thiazine (163 g, yield 60%).

<Step 3> Synthesis of 2- (2- Nitrophenyl ) -4-tosyl-4H- Benzo [b] [1,4] thiazine synthesis

To a solution of 3- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) -4-tosyl-4H-benzo [b] [1 , 4-thiazine (163 g, 0.229 mol), 1-bromo-2-nitrobenzene (57 g, 0.282 mol) and Pd (PPh ₃ ) ₄ (13.5 g, 0.011 mol) ₂ CO ₃ saturated aqueous solution (352 ml) and 1,4-dioxane (2 L) were added and dissolved, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound 2- (2-nitrophenyl) -4-tosyl-4H-benzo [b] [1,4] thiazine , Yield: 92%).

&Lt; Step 4 > Inv3 synthesis

Benzo [b] [1,4] thiazine (89 g, 0.212 mol) and triphenylphosphine (139 g, 0.212 mol) obtained in the above Step 3 in a nitrogen stream, 0.53 mol) and 1,2-dichlorobenzene (1 L) were mixed, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain Compound Inv3 (58 g, yield 70%).

[ Preparation Example 4] Compound Of Inv4 synthesis

&Lt; Step 1 > 3- Bromo -4-tosyl-4H- Benzo [b] [1,4] oxazine synthesis

Acetone (2 L) was added to KOH (280 g, 5.0 mol) and dissolved. Then, 3-bromo-4H-benzo [b] [1,4] oxazine (106 g, 0.50 mol) was added. TsCl (105 g, 0.55 mol) was added and the mixture was refluxed for 3 hours and then cooled. Cold water (3 L) was poured while stirring. After stirring for 30 minutes, the crude product was obtained by filtration. After recrystallization from CH ₂ Cl ₂ / EtOH 3-bromo-4-tosyl-4H-benzo [b] [1,4] oxazine (139 g, yield 76%) was obtained.

&Lt; Step 2 > 3- (4,4,5,5- Tetramethyl -1,3,2- Dioxaborolane Yl) -4-tosyl-4H- Benzo [b] [1,4] oxazine synthesis

Benzo [b] [1,4] oxazine (139 g, 0.38 mol), 4,4,4 ', 4', 5,5, (115.8 g, 0.46 mol), Pd (dppf) Cl ₂ (31 g, 0.038 mol), and 5 ', 5'-octamethyl-2,2'- KOAc (111.9 g, 1.14 mol) was placed in a flask, 1,4-dioxane (2 L) was added thereto, and the mixture was heated and stirred for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Yl) -4-tosyl-4H-benzo [b] [1,4] oxazine (94 g, yield 60%).

<Step 3> Synthesis of 2- (2- Nitrophenyl ) -4-tosyl-4H- Benzo [b] [1,4] oxazine synthesis

To a solution of 3- (4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl) -4-tosyl-4H-benzo [b] [1 2-nitrobenzene (57 g, 0.282 mol) and Pd (PPh ₃ ) ₄ (13.5 g, 0.011 mol) were placed in a flask, and 2M Na ₂ CO ₃ saturated aqueous solution (352 ml) and 1,4-dioxane (2 L) were added and dissolved, followed by heating and stirring for 8 hours. After completion of the reaction, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain 86 g of 2- (2-nitrophenyl) -4-tosyl-4H-benzo [ , Yield: 92%).

&Lt; Step 4 > Inv3 synthesis

Benzo [b] [1,4] oxazine (86 g, 0.212 mol) obtained in the above Step 3 and triphenylphosphine (139 g, 0.53 mol) and 1,2-dichlorobenzene (1 L) were mixed, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain Compound Inv 4 (56 g, yield 70%).

[ Preparation Example 5] Compound Of Inv5 synthesis

&Lt; Step 1 > 3- Bromo -4-tosyl-4H- Benzo [b] [1,4] thiazine synthesis

<Step 2> Synthesis of N-phenyl-4-tosyl-4H- Benzo [b] [1,4] thiazine -3- Amine synthesis

Benzo [b] [1,4] thiazine (145 g, 0.38 mol) and aniline (35 g, 0.38 mol) obtained in the above Step 1 were dissolved in toluene (2 L) The following Pd ₂ (dba) ₃ (34.8 g, 37.9 mmol) was added under nitrogen. Then, NaOtBu (109.5 g, 1.14 mol) was added and X-Phos (18 g, 37.9 mmol) was added to the reaction solution, and the mixture was refluxed with stirring for 5 hours.

After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure and then purified by column chromatography to obtain 123 g of compound N-phenyl-4-tosyl-4H-benzo [b] [1,4] thiazin- 82%).

&Lt; Step 3 > Inv5 Synthesis of

Benzo [b] [1,4] thiazin-3-amine (123 g, 0.31 mol) obtained in the above Step 2 and Pd (OAc) 2 , 31 mmol), K2CO3 (4.3 g, 31 mmol) and PIVOH (60 ml) were added, and the mixture was stirred at 110 DEG C for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain a compound Inv 4 (73 g, yield 60%).

[ Preparation Example 6] compound Inv6 Synthesis of

&Lt; Step 1 > 3- Bromo -4-tosyl-4H- Benzo [b] [1,4] oxazine synthesis

To the solution was added acetone (2 L) in KOH (280 g, 5.0 mol) and then 3-bromo-4H-benzo [b] [1,4] oxazine (106 g, 0.50 mol) was added. TsCl (105 g, 0.55 mol) was added and the mixture was refluxed for 3 hours and then cooled. Cold water (3 L) was poured while stirring. After stirring for 30 minutes, the crude product was obtained by filtration. After recrystallization from CH ₂ Cl ₂ / EtOH 3-bromo-4-tosyl-4H-benzo [b] [1,4] oxazine (139 g, yield 76%) was obtained.

<Step 2> Synthesis of N-phenyl-4-tosyl-4H- Benzo [b] [1,4] oxazine -3- Amine synthesis

4-oxo [b] [1,4] oxazine (139 g, 0.38 mol) and aniline (35 g, 0.38 mol) obtained in the above Step 1 were dissolved in toluene (2 L) The following Pd ₂ (dba) ₃ (34.8 g, 37.9 mmol) was added under nitrogen. Then, NaOtBu (109.5 g, 1.14 mol) was added and X-Phos (18 g, 37.9 mmol) was added to the reaction solution, and the mixture was refluxed with stirring for 5 hours.

After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain 118 g of compound N-phenyl-4-tosyl-4H-benzo [ 82%).

&Lt; Step 3 > Inv5 Synthesis of

Benzo [b] [1,4] oxazine-3-amine (118 g, 0.31 mol) obtained in the above Step 2 and 6.9 g , 31 mmol), K2CO3 (4.3 g, 31 mmol) and PIVOH (60 ml) were added, and the mixture was stirred at 110 DEG C for 12 hours. After completion of the reaction, the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain Compound Inv 4 (70 g, yield 60%).

[ Synthetic example One] Of Cpd1 synthesis

N-phenylnaphthalen-1 -amine (5.4 g, 12.0 mmol) was added to a solution of Inter 1 (2.5 g, 10.0 mmol) and N- (4'-bromo- [ Was dissolved in 100 ml of toluene, and then Pd ₂ (dba) ₃ (0.9 g, 1.0 mmol) was added under nitrogen. Then, NaOtBu (2.9 g, 30 mmol) was added, and (t-Bu) ₃ P (1.0 mL, 1.0 mmol) was added to the reaction solution and the mixture was refluxed with stirring for 5 hours.

After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain a compound Cpd 1 (5.4 g, yield 86%).

HRMS [M] < ⁺ & gt ^; : 642.169

[ Synthetic example 2] Cpd3 Synthesis of

Instead of N, N-di ([1,1'-biphenyl] -4-yl) -N-phenylnaphthalen-1-amine in place of N- (4'- -Yl) -4'-bromo- [1,1'-biphenyl] -4-amine was used in place of 4-bromo-4'-

HRMS [M] < ⁺ & gt ^; : 726.216

[ Synthetic example 3] Cpd4 Synthesis of

([1,1'-biphenyl] -4-yl) -N-phenyl naphthalene-1-amine instead of N- (4'-bromo- [ Except for using N1- (4'-bromo- [1,1'-biphenyl] -4-yl) -N4, N4-diphenylbenzene- The title compound Cpd4 was obtained.

HRMS [M] < ⁺ & gt ^; : 817.259

[ Synthetic example 4] Cpd5 Synthesis of

([1,1'-biphenyl] -4-yl) -N-phenyl naphthalene-1-amine instead of N- (4'-bromo- [ -9,9-dimethyl-9H-fluoren-2-amine was used in place of N- [4'-Bromo- [1,1'-biphenyl] 1, the title compound Cpd5 was obtained.

HRMS [M] < ⁺ & gt ^; : 766.248

[ Synthetic example 5] Cpd9 Synthesis of

([1,1'-biphenyl] -4-yl) -N-phenyl naphthalene-1-amine instead of N- (4'-bromo- [ The same procedure as in Synthesis Example 1 was carried out except that 4'-bromo-N-phenyl- [1,1 ': 4', 1 "-terphenyl] To obtain the title compound Cpd9.

HRMS [M] < ⁺ & gt ^; : 726.216

[ Synthetic example 6] Cpd13 Synthesis of

The same procedure as in Synthesis Example 1 was carried out except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd 13.

HRMS [M] < ⁺ & gt ^; : 592.215

[ Synthetic example 7] Cpd15 Synthesis of

The same procedure as in Synthesis Example 2 was carried out except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd 15.

HRMS [M] < ⁺ & gt ^; : 694.262

[ Synthetic example 8] Cpd16 Synthesis of

The procedure of Synthesis Example 3 was repeated except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd 16.

HRMS [M] < ⁺ & gt ^; : 785.304

[ Synthetic example 9] Cpd17 Synthesis of

The same procedure as in Synthesis Example 4 was carried out except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd 17.

HRMS [M] < ⁺ & gt ^; : 734.293

[ Synthetic example 10] Cpd21 Synthesis of

The same procedure as in Synthesis Example 5 was conducted except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd 21.

HRMS [M] < ⁺ & gt ^; : 694.262

[ Synthetic example 11] Cpd25 Synthesis of

<Step 1> Synthesis of N-phenyl-N- (4 '- (11- Tosylbenzo [5,6] [1,4] thiazino [2,3-b] indole-6 (11H) -yl) - [1,1'-biphenyl] -4- yl) naphthalen-

N-phenylnaphthalen-1 -amine (5.4 g, 12.0 mmol) was added to a solution of the compound of Example 1 (3.9 g, 10.0 mmol) and N- (4'-bromo- [ Was dissolved in 100 ml of toluene, and then Pd ₂ (dba) ₃ (0.9 g, 1.0 mmol) was added under nitrogen. Then, NaOtBu (2.9 g, 30 mmol) was added, and (t-Bu) ₃ P (1.0 mL, 1.0 mmol) was added to the reaction solution and the mixture was refluxed with stirring for 5 hours.

After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound N-phenyl-N- (4 '- (11-tosylbenzo [5,6] [1,4] thiazino [ , 3-b] indol-6 (11H) -yl) - [1,1'-biphenyl] -4-yl) naphthalen-1 -amine (6.5 g, yield 86%).

<Step 2> Synthesis of N- (4 '- ( Benzo [5,6] [1,4] thiazino [2,3-b] indole -6 (11H) -yl) - [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen-

(4'- (11-Tocylbenzo [5,6] [1,4] thiazino [2,3-b] indol-6 (11H) -yl) (6.5 g, 8.5 mmol), NaOH (3.4 g, 85 mmol), THF 40 mL, MeOH 20 mL, water 20 mL was added to a 250 mL round flask. The reaction was heated to reflux for 12 h. After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain the compound N- (4 '- (benzo [5,6] [1,4] thiazino [2,3- b] 6 (11H) -yl) - [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- 1 -amine (4.6 g, yield 90%).

&Lt; Step 3 > Cpd25 Synthesis of

(4'- (benzo [5,6] [1,4] thiazino [2,3-b] indole-6 (11H) -yl) - [ 1-amine (4.6 g, 7.5 mmol) and bromobenzene (1.4 g, 9.0 mmol) were dissolved in 100 ml of toluene, and then Pd ₂ (dba) ₃ g, 0.8 mmol) were added under nitrogen. Thereafter, NaOtBu (2.2 g, 22.9 mmol) was added, and (t-Bu) ₃ P (0.8 ml, 0.8 mmol) was added to the reaction solution and the mixture was refluxed with stirring for 5 hours.

After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over Na ₂ SO ₄ , distilled under reduced pressure, and then purified by column chromatography to obtain a compound Cpd 25 (4.3 g, yield 85%).

HRMS [M] < ⁺ & gt ^; : 683.240

[ Synthetic example 12] Cpd27 Synthesis of

Instead of N, N-di ([1,1'-biphenyl] -4-yl) -N-phenylnaphthalen-1-amine in place of N- (4'- - yl) -4'-bromo- [1,1'-biphenyl] -4-amine was used in place of 4-bromo-4'-

HRMS [M] < ⁺ & gt ^; : 785.286

[ Synthetic example 13] Cpd28 Synthesis of

([1,1'-biphenyl] -4-yl) -N-phenyl naphthalene-1-amine instead of N- (4'-bromo- [ Except for using N1- (4'-bromo- [1,1'-biphenyl] -4-yl) -N4, N4-diphenylbenzene- The title compound Cpd28 was obtained.

HRMS [M] < ⁺ & gt ^; : 876.329

[ Synthetic example 14] Cp29 Synthesis of

([1,1'-biphenyl] -4-yl) -N-phenyl naphthalene-1-amine instead of N- (4'-bromo- [ -9,9-dimethyl-9H-fluoren-2-amine was used in place of N- [4'-Bromo- [1,1'-biphenyl] 11, the title compound Cpd29 was obtained.

HRMS [M] < ⁺ & gt ^; : 825.318

[ Synthetic example 15] Cpd32 Synthesis of

([1,1'-biphenyl] -4-yl) -N-phenyl naphthalene-1-amine instead of N- (4'-bromo- [ The same procedure as in Synthesis Example 11 was carried out except that 4'-bromo-N-phenyl- [1,1 ': 4', 1 "-terphenyl] To obtain the title compound Cpd32.

HRMS [M] < ⁺ & gt ^; : 785.286

[ Synthetic example 16] Cpd34 Synthesis of

The same procedure as in Synthesis Example 11 was carried out, except that Inv 5 was used instead of Inv 3 to obtain the title compound Cpd34.

HRMS [M] < ⁺ & gt ^; : 683.240

[ Synthetic example 17] Cpd36 Synthesis of

The same procedure as in Synthesis Example 11 was conducted except that Inv 5 was used instead of Inv 3 to obtain the title compound Cpd36.

HRMS [M] < ⁺ & gt ^; : 785.286

[ Synthetic example 18] Cpd37 Synthesis of

The same procedure as in Synthesis Example 11 was carried out, except that Inv 5 was used instead of Inv 3 to obtain the title compound Cpd37.

HRMS [M] < ⁺ & gt ^; : 876.329

[ Synthetic example 19] Cp38 Synthesis of

The same procedure as in Synthesis Example 11 was conducted except that Inv 5 was used instead of Inv 3 to obtain the title compound Cpd38.

HRMS [M] < ⁺ & gt ^; : 825.318

[ Synthetic example 20] Cpd41 Synthesis of

The same procedure as in Synthesis Example 11 was carried out, except that Inv 5 was used instead of Inv 3 to obtain the title compound Cpd41.

HRMS [M] < ⁺ & gt ^; : 785.286

[ Synthetic example 21] Cpd43 Synthesis of

The same procedure as in Synthesis Example 11 was conducted except that Inv 4 was used instead of Inv 3 to obtain the title compound Cpd43.

HRMS [M] < ⁺ & gt ^; : 667.262

[ Synthetic example 22] Cpd45 Synthesis of

The same procedure as in Synthesis Example 12 was carried out, except that Inv 4 was used instead of Inv 3 to obtain the title compound Cpd45.

HRMS [M] < ⁺ & gt ^; : 769.309

[ Synthetic example 23] Cpd46 Synthesis of

The same procedure as in Synthesis Example 13 was conducted except that Inv 4 was used instead of Inv 3 to obtain the title compound Cpd46.

HRMS [M] < ⁺ & gt ^; : 860.352

[ Synthetic example 24] Cp47 Synthesis of

The same procedure as in Synthesis Example 14 was carried out, except that Inv 4 was used instead of Inv 3 to obtain the title compound Cpd47.

HRMS [M] < ⁺ & gt ^; : 809.341

[ Synthetic example 25] Cpd50 Synthesis of

The same procedure as in Synthesis Example 15 was conducted except that Inv 4 was used instead of Inv 3 to obtain the title compound Cpd50.

HRMS [M] < ⁺ & gt ^; : 769.309

[ Synthetic example 26] Cpd52 Synthesis of

The same procedure as in Synthesis Example 11 was carried out, except that Inv 6 was used instead of Inv 3 to obtain the title compound Cpd52.

HRMS [M] < ⁺ & gt ^; : 667.262

[ Synthetic example 27] Cpd54 Synthesis of

The same procedure as in Synthesis Example 12 was conducted except that Inv 6 was used instead of Inv 3 to obtain the title compound Cpd54.

HRMS [M] < ⁺ & gt ^; : 769.309

[ Synthetic example 28] Cpd55 Synthesis of

The same procedure as in Synthesis Example 13 was conducted except that Inv 6 was used instead of Inv 3 to obtain the title compound Cpd55.

HRMS [M] < ⁺ & gt ^; : 860.352

[ Synthetic example 29] Cp56 Synthesis of

The same procedure as in Synthesis Example 14 was carried out, except that Inv 6 was used instead of Inv 3 to obtain the title compound Cpd56.

HRMS [M] < ⁺ & gt ^; : 809.341

[ Synthetic example 30] Cpd59 Synthesis of

The same procedure as in Synthesis Example 15 was conducted except that Inv 6 was used instead of Inv 3 to obtain the title compound Cpd59.

HRMS [M] < ⁺ & gt ^; : 769.309

[ Synthetic example 31] Cpd65 Synthesis of

Instead of 2-chloro-4,6-diphenyl-1,3,5-trifluorobenzene instead of N- (4'-bromo- [1,1'- The procedure of Synthetic Example 1 was repeated except that triazine was used to obtain the title compound Cpd65.

HRMS [M] < ⁺ & gt ^; : 486.097

[ Synthetic example 32] Cpd Synthesis of 69

Instead of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenyl naphthalen- The same procedure as in Synthesis Example 1 was carried out, except that 1,3,5-triazine was used to obtain the title compound Cpd69.

HRMS [M] < ⁺ & gt ^; : 562.129

[ Synthetic example 33] Cpd Synthesis of 73

Instead of 2- (3-chlorophenyl) -4,6-diphenyl-1-amine in place of N- (4'-bromo- [ , 3,5-triazine was used in place of 3,5-triazinecarboxylic acid, to obtain the title compound Cpd73.

HRMS [M] < ⁺ & gt ^; : 562.129

[ Synthetic example 34] Cpd Synthesis of 76

Except that 2- (3-chlorophenyl) -4,6-diphenylpyrimidine was used instead of N- (4'-bromo- [1,1'-biphenyl] The procedure of Synthesis Example 1 was repeated to obtain the title compound Cpd76.

HRMS [M] < ⁺ & gt ^; : 561.133

[ Synthetic example 35] Cpd79 Synthesis of

Instead of 2- (4'-chloro- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- 3-yl) -4,6-diphenyl-1,3,5-triazine was used in place of the compound obtained in Synthesis Example 1 to obtain the title compound Cpd79.

HRMS [M] < ⁺ & gt ^; : 638.160

[ Synthetic example 36] Cpd Synthesis of 80

Instead of 2- (4'-chloro- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- -4-yl) -4,6-diphenyl-1,3,5-triazine was used in place of the compound obtained in Synthesis Example 1 to obtain the title compound Cpd80.

HRMS [M] < ⁺ & gt ^; : 638.160

[ Synthetic example 37] Cpd81 Synthesis of

Instead of 2- (3'-chloro- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- 3-yl) -4,6-diphenyl-1,3,5-triazine was used in place of the compound obtained in Synthesis Example 1 to obtain the title compound Cpd81.

HRMS [M] < ⁺ & gt ^; : 638.160

[ Synthetic example 38] Cpd82 Synthesis of

Instead of 2- (3'-chloro- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- -4-yl) -4,6-diphenyl-1,3,5-triazine was used in place of the compound obtained in Synthesis Example 1 to obtain the title compound Cpd82.

HRMS [M] < ⁺ & gt ^; : 638.160

[ Synthetic example 39] Cpd Synthesis of 83

Instead of 2 - ([1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- 1 -amine instead of N- (4'- Phenyl) -1,3,5-triazine was used in place of the compound obtained in Synthesis Example 1, except that 3-chloro-4- (3'-chloro- [ Was carried out to obtain the title compound Cpd83.

HRMS [M] < ⁺ & gt ^; : 714.191

[ Synthetic example 40] Cpd Synthesis of 90

Except that 2- (3-chlorophenyl) triphenylene was used instead of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N- phenyl naphthalen- , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd90.

HRMS [M] < ⁺ & gt ^; : 557.127

[ Synthetic example 41] Cpd Synthesis of 95

9-phenyl-9H-carbazole instead of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd95.

HRMS [M] < ⁺ & gt ^; : 496.107

[ Synthetic example 42] Cpd Synthesis of 96

Except that 4-bromodibenzo [b, d] furan was used instead of N- (4'-bromo- [1,1'-biphenyl] , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd96.

HRMS [M] < ⁺ & gt ^; : 421.060

[ Synthetic example 43] Cpd Synthesis of 97

Except that 4-bromodibenzo [b, d] thiophene was used instead of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd97.

HRMS [M] < ⁺ & gt ^; : 437.037

[ Synthetic example 44] Cpd 98 Synthesis

Except that 2-bromodibenzo [b, d] furan was used instead of N- (4'-bromo- [1,1'-biphenyl] , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd98.

HRMS [M] < ⁺ & gt ^; : 421.060

[ Synthetic example 45] Cpd Synthesis of 99

Except that 2-bromodibenzo [b, d] thiophene was used instead of N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen- , The same procedure as in Synthesis Example 1 was carried out to obtain the title compound Cpd99.

HRMS [M] < ⁺ & gt ^; : 437.037

[ Synthetic example 46] Cpd Synthesis of 100

Bromo-9- (dibenzo [b, d] thiophene instead of N- (4'-bromo- [1,1'-biphenyl] -2-yl) -9H-carbazole was used in place of the compound obtained in Preparation Example 1, the title compound Cpd100 was obtained.

HRMS [M] < ⁺ & gt ^; : 602.095

[ Synthetic example 47] Cpd Synthesis of 101

Bromo-9- (dibenzo [b, d] thiophene instead of N- (4'-bromo- [1,1'-biphenyl] -2-yl) -9H-carbazole was used in place of the compound obtained in Synthesis Example 1, the title compound Cpd101 was obtained.

HRMS [M] < ⁺ & gt ^; : 661.165

[ Synthetic example 48] Cpd Synthesis of 102

Bromo-9- (dibenzo [b, d] furan-2-yl) -amine instead of N- (4'- 2-yl) -9H-carbazole was used in place of the compound of Preparation Example 1, the title compound Cpd102 was obtained.

HRMS [M] < ⁺ & gt ^; : 586.117

[ Synthetic example 49] Of Cpd107 synthesis

The same procedure as in Synthesis Example 31 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd107.

HRMS [M] < ⁺ & gt ^; : 454.143

[ Synthetic example 50] Cpd Synthesis of 111

The same procedure as in Synthesis Example 32 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd111.

HRMS [M] < ⁺ & gt ^; : 530.174

[ Synthetic example 51] Cpd Synthesis of 115

The same procedure as in Synthesis Example 33 was conducted except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd115.

HRMS [M] < ⁺ & gt ^; : 530.174

[ Synthetic example 52] Cpd Synthesis of 119

The procedure of Synthetic Example 34 was followed except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd119.

HRMS [M] < ⁺ & gt ^; : 529.179

[ Synthetic example 53] Of Cpd121 synthesis

The same procedure as in Synthesis Example 35 was conducted except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd121.

HRMS [M] < ⁺ & gt ^; : 606.206

[ Synthetic example 54] Of Cpd122 synthesis

The same procedure as in Synthesis Example 36 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd122.

HRMS [M] < ⁺ & gt ^; : 606.206

[ Synthetic example 55] Cpd123 Synthesis of

The same procedure as in Synthesis Example 37 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd123.

HRMS [M] < ⁺ & gt ^; : 606.206

[ Synthetic example 56] Cpd124 Synthesis of

The same procedure as in Synthesis Example 38 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd124.

HRMS [M] < ⁺ & gt ^; : 606.206

[ Synthetic example 57] Of Cpd125 synthesis

The same procedure as in Synthesis Example 39 was conducted except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd125.

HRMS [M] < ⁺ & gt ^; : 682.237

[ Synthetic example 58] Of Cpd131 synthesis

The same procedure as in Synthesis Example 40 was conducted except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd131.

HRMS [M] < ⁺ & gt ^; : 525.173

[ Synthetic example 59] Of Cpd136 synthesis

The same procedure as in Synthesis Example 41 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd136.

HRMS [M] < ⁺ & gt ^; : 464.152

[ Synthetic example 60] Of Cpd137 synthesis

The same procedure as in Synthesis Example 42 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd137.

HRMS [M] < ⁺ & gt ^; : 389.105

[ Synthetic example 61] Of Cpd138 synthesis

The same procedure as in Synthesis Example 43 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd138.

HRMS [M] < ⁺ & gt ^; : 405.082

[ Synthetic example 62] Of Cpd139 synthesis

The same procedure as in Synthesis Example 44 was conducted, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd139.

HRMS [M] < ⁺ & gt ^; : 389.105

[ Synthetic example 63] Of Cpd140 synthesis

The same procedure as in Synthesis Example 45 was conducted except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd140.

HRMS [M] < ⁺ & gt ^; : 405.082

[ Synthetic example 64] Of Cpd141 synthesis

The same procedure as in Synthesis Example 46 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd141.

HRMS [M] < ⁺ & gt ^; : 570.140

[ Synthetic example 65] Of Cpd142 synthesis

The same procedure as in Synthesis Example 47 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd142.

HRMS [M] < ⁺ & gt ^; : 629.210

[ Synthetic example 66] Of Cpd143 synthesis

The same procedure as in Synthesis Example 48 was carried out, except that Inv 2 was used instead of Inv 1 to obtain the title compound Cpd143.

HRMS [M] < ⁺ & gt ^; : 554.163

[ Synthetic example 67] Of Cpd148 synthesis

The same procedure as in Synthesis Example 31 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd148.

HRMS [M] < ⁺ & gt ^; : 545.167

[ Synthetic example 68] Cpd Synthesis of 152

The same procedure as in Synthesis Example 32 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd152.

HRMS [M] < ⁺ & gt ^; : 621.199

[ Synthetic example 69] Cpd 156 Synthesis

The same procedure as in Synthesis Example 33 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd156.

HRMS [M] < ⁺ & gt ^; : 621.199

[ Synthetic example 70] Cpd Synthesis of 159

The procedure of Synthetic Example 34 was performed, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd 159.

HRMS [M] < ⁺ & gt ^; : 620.203

[ Synthetic example 71] Of Cpd162 synthesis

The same procedure as in Synthesis Example 35 was conducted except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd 162.

HRMS [M] < ⁺ & gt ^; : 697.230

[ Synthetic example 72] Of Cpd163 synthesis

The same procedure as in Synthesis Example 36 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd 163.

HRMS [M] < ⁺ & gt ^; : 697.230

[ Synthetic example 73] Cpd164 Synthesis of

The same procedure as in Synthesis Example 37 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd 164.

HRMS [M] < ⁺ & gt ^; : 697.230

[ Synthetic example 74] Cpd165 Synthesis of

The same procedure as in Synthesis Example 38 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd165.

HRMS [M] < ⁺ & gt ^; : 697.230

[ Synthetic example 75] Of Cpd166 synthesis

The same procedure as in Synthesis Example 39 was conducted, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd 166.

HRMS [M] < ⁺ & gt ^; : 773.261

[ Synthetic example 76] Of Cpd172 synthesis

The same procedure as in Synthesis Example 40 was conducted except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd172.

HRMS [M] < ⁺ & gt ^; : 616.197

[ Synthetic example 77] Of Cpd177 synthesis

The same procedure as in Synthesis Example 41 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd177.

HRMS [M] < ⁺ & gt ^; : 555.177

[ Synthetic example 78] Of Cpd178 synthesis

The same procedure as in Synthesis Example 42 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd178.

HRMS [M] < ⁺ & gt ^; : 480.130

[ Synthetic example 79] Of Cpd179 synthesis

The same procedure as in Synthesis Example 43 was conducted, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd179.

HRMS [M] < ⁺ & gt ^; : 496.107

[ Synthetic example 80] Cpd180's synthesis

The same procedure as in Synthesis Example 44 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd180.

HRMS [M] < ⁺ & gt ^; : 480.130

[ Synthetic example 81] Of Cpd181 synthesis

The same procedure as in Synthesis Example 45 was conducted, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd181.

HRMS [M] < ⁺ & gt ^; : 496.107

[ Synthetic example 82] Of Cpd182 synthesis

The same procedure as in Synthesis Example 46 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd 182.

HRMS [M] < ⁺ & gt ^; : 661.165

[ Synthetic example 83] Of Cpd183 synthesis

The same procedure as in Synthesis Example 47 was conducted, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd 183.

HRMS [M] < ⁺ & gt ^; : 720.235

[ Synthetic example 84] Of Cpd184 synthesis

The same procedure as in Synthesis Example 48 was carried out, except that Inv 3 was used instead of Inv 1 to obtain the title compound Cpd 184.

HRMS [M] < ⁺ & gt ^; : 645.187

[ Synthetic example 85] Of Cpd189 synthesis

The same procedure as in Synthesis Example 31 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd189.

HRMS [M] < ⁺ & gt ^; : 529.190

[ Synthetic example 86] Cpd Synthesis of 193

The same procedure as in Synthesis Example 32 was conducted except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd 193.

HRMS [M] < ⁺ & gt ^; : 605.222

[ Synthetic example 87] Cpd 197 Synthesis

The same procedure as in Synthesis Example 33 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd197.

HRMS [M] < ⁺ & gt ^; : 605.222

[ Synthetic example 88] Cpd 200 Synthesis

The same procedure as in Synthesis Example 34 was conducted except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd200.

HRMS [M] < ⁺ & gt ^; : 604.226

[ Synthetic example 89] Of Cpd203 synthesis

The same procedure as in Synthesis Example 35 was conducted except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd203.

HRMS [M] < ⁺ & gt ^; : 681.253

[ Synthetic example 90] Of Cpd204 synthesis

The same procedure as in Synthesis Example 36 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd204.

HRMS [M] < ⁺ & gt ^; : 681.253

[ Synthetic example 91] Cpd205 Synthesis of

The same procedure as in Synthesis Example 37 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd205.

HRMS [M] < ⁺ & gt ^; : 681.253

[ Synthetic example 92] Cpd206 Synthesis of

The same procedure as in Synthesis Example 38 was conducted except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd206.

HRMS [M] < ⁺ & gt ^; : 681.253

[ Synthetic example 93] Of Cpd207 synthesis

The same procedure as in Synthesis Example 39 was conducted except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd207.

HRMS [M] < ⁺ & gt ^; : 757.284

[ Synthetic example 94] Of Cpd213 synthesis

The same procedure as in Synthesis Example 40 was conducted except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd213.

HRMS [M] < ⁺ & gt ^; : 600.220

[ Synthetic example 95] Of Cpd218 synthesis

The same procedure as in Synthesis Example 41 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd218.

HRMS [M] < ⁺ >: 539.200

[ Synthetic example 96] Of Cpd219 synthesis

The same procedure as in Synthesis Example 42 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd219.

HRMS [M] < ⁺ & gt ^; : 464.152

[ Synthetic example 97] Of Cpd220 synthesis

The same procedure as in Synthesis Example 43 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd220.

HRMS [M] < ⁺ & gt ^; : 480.130

[ Synthetic example 98] Of Cpd221 synthesis

The same procedure as in Synthesis Example 44 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd221.

HRMS [M] < ⁺ & gt ^; : 464.152

[ Synthetic example 99] Of Cpd222 synthesis

The same procedure as in Synthesis Example 45 was conducted except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd222.

HRMS [M] < ⁺ & gt ^; : 480.130

[ Synthetic example 100] Of Cpd223 synthesis

The same procedure as in Synthesis Example 46 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd223.

HRMS [M] < ⁺ & gt ^; : 645.187

[ Synthetic example 101] Of Cpd224 synthesis

The same procedure as in Synthesis Example 47 was carried out, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd224.

HRMS [M] < ⁺ & gt ^; : 704.258

[ Synthetic example 102] Of Cpd225 synthesis

The same procedure as in Synthesis Example 48 was conducted, except that Inv 4 was used instead of Inv 1 to obtain the title compound Cpd225.

HRMS [M] < ⁺ & gt ^; : 629.210

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

The compound Cpd1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was prepared as follows.

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

M-MTDATA (60 nm) / TCTA (80 nm) / compound cpd65 (40 nm) / CBP + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) in this order to form an organic electroluminescent device.

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

[ Example 2 ~ 30] Green organic Field Fabrication of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the compound shown in the following Table 1 was used in place of the compound Cpd1 used in Example 1, respectively.

[ 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 the compound Cpd1 used in Example 1 was not used.

[ Evaluation example One]

The driving voltage, current efficiency and emission peak at a current density of 10 mA / cm 2 were measured for the green organic electroluminescent device manufactured in each of Examples 1 to 30 and Comparative Example 1, .

Sample Light-emitting auxiliary layer material The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 1 Cpd1 6.80 517 42.0 Example 2 Cpd3 6.85 518 41.9 Example 3 Cpd4 6.71 520 41.5 Example 4 Cpd5 6.85 518 41.8 Example 5 Cpd9 6.85 520 41.8 Example 6 Cpd13 6.80 519 41.5 Example 7 Cpd15 6.90 518 41.8 Example 8 Cpd16 6.85 520 41.5 Example 9 Cpd17 6.73 518 41.5 Example 10 Cpd21 6.74 520 41.8 Example 11 Cpd25 6.75 518 41.8 Example 12 Cpd27 6.80 517 41.5 Example 13 Cpd28 6.77 518 42.0 Example 14 Cpd29 6.72 520 41.9 Example 15 Cpd32 6.80 518 41.5 Example 16 Cpd34 6.69 520 41.8 Example 17 Cpd36 6.82 517 41.8 Example 18 Cpd37 6.75 518 41.8 Example 19 Cpd38 6.80 520 42.0 Example 20 Cpd41 6.77 518 42.0 Example 21 Cpd43 6.85 520 41.5 Example 22 Cpd45 6.80 519 41.8 Example 23 Cpd46 6.90 517 41.8 Example 24 Cpd47 6.70 518 41.5 Example 25 Cpd50 6.73 520 41.8 Example 26 Cpd52 6.74 518 42.0 Example 27 Cpd54 6.69 520 41.8 Example 28 Cpd55 6.80 520 41.5 Example 29 Cpd56 6.71 519 41.8 Example 30 Cpd59 6.85 517 41.5 Comparative Example 1 - 6.93 516 38.2

As shown in Table 1, in the green organic electroluminescent devices of Examples 1 to 30 using the compounds (Cpd1 to Cpd59) represented by the formula (1) according to the present invention as the light emitting auxiliary layer material, only CBP It was found that the driving voltage was slightly lower than that of the green organic electroluminescent device of Comparative Example 1 and the current efficiency was better than that of the green organic electroluminescent device of Comparative Example 1. [

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

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned with distilled water ultrasonic wave. After the distilled water was cleaned, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a UV OZONE cleaner (Powersonic 405, Hwasin Tech). Then, the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

(60 nm) / TCTA (80 nm) / compound cpd1 (40 nm) / CBP + 10% (piq) ₂ Ir (acac) (300 nm) / BCP (10 nm) / on the ITO transparent electrode thus prepared, Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce an organic electroluminescent device.

The structures of m-MTDATA, TCTA, CBP and BCP used herein are as described in Example 1, and (piq) ₂ Ir (acac) is as follows.

[ Example 32 ~ 60] 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 the compound shown in the following Table 2 was used in place of the compound Cpd1 used in Example 31.

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

A red organic electroluminescent device was manufactured in the same manner as in Example 59 except that the compound Cpd1 used in Example 31 was not used.

[ Evaluation example 2]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each red organic electroluminescent device fabricated in Examples 31 to 60 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Light-emitting auxiliary layer material The driving voltage (V) Current efficiency (cd / A) Example 31 Cpd1 5.15 10.8 Example 32 Cpd3 5.10 11.2 Example 33 Cpd4 5.15 11.0 Example 34 Cpd5 5.20 10.8 Example 35 Cpd9 5.15 11.2 Example 36 Cpd13 5.10 11.0 Example 37 Cpd15 5.15 11.3 Example 38 Cpd16 5.10 11.0 Example 39 Cpd17 5.15 11.3 Example 40 Cpd21 5.20 10.8 Example 41 Cpd25 5.13 11.1 Example 42 Cpd27 5.16 11.5 Example 43 Cpd28 5.17 11.6 Example 44 Cpd29 5.14 11.0 Example 45 Cpd32 5.15 10.8 Example 46 Cpd34 5.10 11.2 Example 47 Cpd36 5.15 11.0 Example 48 Cpd37 5.20 11.3 Example 49 Cpd38 5.15 11.0 Example 50 Cpd41 5.10 11.3 Example 51 Cpd43 5.15 10.8 Example 52 Cpd45 5.10 11.1 Example 53 Cpd46 5.15 11.5 Example 54 Cpd47 5.20 10.8 Example 55 Cpd50 5.13 11.2 Example 56 Cpd52 5.20 11.0 Example 57 Cpd54 5.15 10.8 Example 58 Cpd55 5.10 11.2 Example 59 Cpd56 5.15 11.0 Example 60 Cpd59 5.10 11.3 Comparative Example 2 - 5.25 8.2

As shown in Table 2, in the red organic electroluminescent devices of Examples 31 to 60, in which the compound represented by Chemical Formula 1 (compounds Cpd1 to Cpd59) according to the present invention was used as the light emitting auxiliary layer material, only CBP As compared with the red organic electroluminescent device of Comparative Example 2 used as the light emitting layer material, it was found that the driving voltage was slightly lower and the current efficiency was better.

[ Example 61] Blue organic Field Fabrication of light emitting device

The compound Cpd1 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.

First, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned 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, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Powersonic 405, Hoshin Tec), the substrate was cleaned using UV for 5 minutes, The substrate was transferred to an evaporator.

On the ITO transparent electrode thus prepared, a mixture of DS-205 (80 nm) / NPB (15 nm) / compound Cpd 1 (15 nm) / ADN + 5% DS-405 (Doosan) (300 nm) / BCP ) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to produce an organic electroluminescent device.

The BCP used is as described in Example 1, and the structures of NPB and ADN are as follows.

[ Example 62 ~ 90] Blue organic Field Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 61 except that the compound shown in the following Table 3 was used in place of the compound Cpd1 used in Example 61, respectively.

[ Comparative Example 3] Blue organic Field Fabrication of light emitting device

A blue organic electroluminescent device was fabricated in the same manner as in Example 61 except that the compound Cpd1 used in Example 61 was not used.

[ Evaluation example 3]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices fabricated in Examples 61 to 90 and Comparative Example 3, and the results are shown in Table 3 below.

Sample Light-emitting auxiliary layer material The driving voltage (V) Current efficiency (cd / A) Example 61 Cpd1 5.50 6.9 Example 62 Cpd3 5.60 6.6 Example 63 Cpd4 5.55 6.8 Example 64 Cpd5 5.60 6.9 Example 65 Cpd9 5.51 6.6 Example 66 Cpd13 5.55 6.8 Example 67 Cpd15 5.51 6.0 Example 68 Cpd16 5.55 6.4 Example 69 Cpd17 5.60 6.0 Example 70 Cpd21 5.65 6.4 Example 71 Cpd25 5.53 6.5 Example 72 Cpd27 5.56 6.8 Example 73 Cpd28 5.49 6.1 Example 74 Cpd29 5.50 6.9 Example 75 Cpd32 5.60 6.6 Example 76 Cpd34 5.55 6.8 Example 77 Cpd36 5.60 6.9 Example 78 Cpd37 5.51 6.6 Example 79 Cpd38 5.55 6.8 Example 80 Cpd41 5.51 6.0 Example 81 Cpd43 5.55 6.4 Example 82 Cpd45 5.60 6.5 Example 83 Cpd46 5.65 6.8 Example 84 Cpd47 5.53 6.1 Example 85 Cpd50 5.56 6.9 Example 86 Cpd52 5.49 6.6 Example 87 Cpd54 5.50 6.8 Example 88 Cpd55 5.60 6.9 Example 89 Cpd56 5.55 6.4 Example 90 Cpd59 5.60 6.5 Comparative Example 3 - 5.60 4.8

As shown in Table 3, the red organic electroluminescent devices of Examples 31 to 60, in which the compounds represented by Formula 1 (compounds Cpd1 to Cpd59) according to the present invention were used as the light emitting auxiliary layer material, The driving voltage was similar to that of the blue organic electroluminescent device of Comparative Example 3 used as the light emitting layer material, but it was found that the current efficiency was better than that of the organic electroluminescent device of Comparative Example 3.

[ Example 91] Green Organic Field Fabrication of light emitting device

Compound Cpd65 was 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, glass substrate coated with ITO (Indium tin oxide) thin film of 1500 Å thickness was cleaned 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 The substrate was transferred to a vacuum evaporator.

(60 nm) / TCTA (80 nm) / compound Cpd65 + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF 1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Example 92 ~ 126] Green organic Field Fabrication of light emitting device

A green organic electroluminescent device was fabricated in the same manner as in Example 91 except that the compound shown in the following Table 4 was used in place of the compound Cpd65 used in Example 91.

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

A green organic electroluminescent device was fabricated in the same manner as in Example 91, except that CBP was used in place of the compound Cpd65 used as a light emitting host material in forming the light emitting layer in Example 91.

[ Evaluation example 4]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm < 2 > were measured for each of the green organic electroluminescent devices manufactured in Examples 91 to 126 and Comparative Example 4. The results are shown in Table 4 .

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 91 Cpd65 6.63 518 40.5 Example 92 Cpd69 6.78 515 42.4 Example 93 Cpd73 6.81 518 41.1 Example 94 Cpd76 6.79 517 40.8 Example 95 Cpd79 6.81 518 41.1 Example 96 Cpd80 6.79 517 40.8 Example 97 Cpd81 6.78 515 42.4 Example 98 Cpd82 6.81 518 41.1 Example 99 Cpd83 6.79 517 40.8 Example 100 Cpd107 6.81 518 41.1 Example 101 Cpd111 6.79 517 40.8 Example 102 Cpd115 6.79 517 40.8 Example 103 Cpd118 6.81 518 41.1 Example 104 Cpd121 6.79 517 40.8 Example 105 Cpd122 6.81 518 41.1 Example 106 Cpd123 6.78 515 42.4 Example 107 Cpd124 6.79 517 40.8 Example 108 Cpd125 6.79 517 40.8 Example 109 Cpd148 6.81 518 41.1 Example 110 Cpd152 6.79 517 40.8 Example 111 Cpd156 6.78 515 42.4 Example 112 Cpd159 6.81 518 41.1 Example 113 Synthesis of Cpd162 6.79 517 40.8 Example 114 Cpd163 6.81 518 41.1 Example 115 Cpd164 6.79 517 40.8 Example 116 Cpd165 6.78 515 42.4 Example 117 Cpd166 6.81 518 41.1 Example 118 Cpd189 6.79 517 40.8 Example 119 Cpd193 6.81 518 41.1 Example 120 Cpd197 6.79 517 40.8 Example 121 Cpd200 6.79 517 40.8 Example 122 Cpd203 6.81 518 41.1 Example 123 Cpd204 6.79 517 40.8 Example 124 Cpd205 6.79 517 40.8 Example 125 Cpd206 6.81 518 41.1 Example 126 Cpd207 6.78 515 42.4 Comparative Example 4 CBP 6.93 516 38.2

As shown in Table 4, in the case of the green organic electroluminescent devices of Examples 91 to 126, in which the synthesized compounds Cpd65 to 207 were used as light emitting layer materials, respectively, compared with the green organic electroluminescent device of Comparative Example 4 using conventional CBP It was found that the device exhibited better performance in terms of efficiency and driving voltage.

[ Example 127] blue organic Field Fabrication of light emitting device

The compound Cpd90 was subjected to high purity sublimation purification by a conventionally known method, and a blue organic electroluminescent device was fabricated according to the following procedure.

The ITO transparent electrode thus prepared was laminated in the order of CuPc (10 nm) / TPAC (30 nm) / compound Cpd90 + 7% Flrpic (30 nm) / Alq ₃ (30 nm) / LiF (0.2 nm) / Al Thereby preparing an organic EL device.

The structures of CuPc, TPAC and Flrpic used herein are as follows.

[ Example 128 ~ 162] Blue organic Field Fabrication of light emitting device

A blue organic electroluminescent device was produced in the same manner as in Example 127 except that the compound shown in the following Table 5 was used in place of the compound Cpd90 used in Example 127.

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

A blue organic electroluminescent device was fabricated in the same manner as in Example 127 except that CBP was used in place of the compound Cdp105 used as a light emitting host material in forming the light emitting layer in Example 127. [

[ Evaluation example 5]

The driving voltage, current efficiency and emission peak at current densities of 10 mA / cm 2 were measured for each of the blue organic electroluminescent devices fabricated in Examples 127 to 162 and Comparative Example 5, and the results are shown in Table 5 .

Sample Host The driving voltage (V) Emission peak (nm) Current efficiency (cd / A) Example 127 Cpd90 7.30 474 6.34 Example 128 Cpd95 7.24 475 6.55 Example 129 Cpd96 7.24 475 6.55 Example 130 Cpd97 7.15 471 6.94 Example 131 Cpd98 7.23 472 6.25 Example 132 Cpd99 7.12 472 5.85 Example 133 Cpd100 7.00 472 6.34 Example 134 Cpd101 7.29 473 6.90 Example 135 Cpd102 7.30 474 6.34 Example 136 Cpd131 7.24 475 6.55 Example 137 Cpd136 7.15 471 6.94 Example 138 Cpd137 7.23 472 6.25 Example 139 Cpd138 7.30 474 6.34 Example 140 Cpd139 7.24 475 6.55 Example 141 Cpd140 7.15 471 6.94 Example 142 [ Cpd141 7.23 472 6.25 Example 143 Cpd142 7.12 472 5.85 Example 144 Cpd143 7.00 472 6.34 Example 145 Cpd172 7.29 473 6.90 Example 146 Cpd177 7.30 474 6.34 Example 147 Cpd178 7.24 475 6.55 Example 148 Cpd179 7.24 475 6.55 Example 149 Cpd180 7.15 471 6.94 Example 150 Cpd181 7.23 472 6.25 Example 151 Cpd182 7.12 472 5.85 Example 152 Cpd183 7.00 472 6.34 Example 153 Cpd184 7.29 473 6.90 Example 154 Cpd213 7.30 474 6.34 Example 155 Cpd218 7.24 475 6.55 Example 156 Cpd219 7.15 471 6.94 Example 157 Cpd220 7.23 472 6.25 Example 158 Cpd221 7.30 474 6.34 Example 159 Cpd222 7.24 475 6.55 Example 160 Cpd223 7.15 471 6.94 Example 161 Cpd224 7.23 472 6.25 Example 162 Cpd225 7.12 472 5.85 Comparative Example 5 CBP 7.80 474 5.80

As shown in Table 5, the blue organic electroluminescent devices of Examples 127 to 162 using the compounds (Cpd90 to Cpd225) according to the present invention as light emitting layer materials were the blue organic electroluminescent devices of Comparative Example 5 using CBP Which is superior in current efficiency and driving voltage.

[ Example 163] Green organic Field Fabrication of light emitting device

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 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 The substrate was transferred to a vacuum evaporator.

(60 nm) / Compound Cpd1 (80 nm) / DS-H522 + 5% DS-501 (300 nm) / BCP (10 nm) / Alq3 (30 nm) / 5 nm as a hole transporting layer material on the ITO transparent electrode prepared as described above. An organic EL device was fabricated in the order of LiF (1 nm) / Al (200 nm).

[ Example 164 ~ 192] Green organic Field Fabrication of light emitting device

A green organic EL device was produced in the same manner as in Example 163 except that the compound described in the following Table 6 was used in place of the compound Cpd1 used in Example 163, respectively.

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

A green organic electroluminescent device was prepared in the same manner as in Example 163, except that NPB was used instead of the compound Cpd1 used in Example 163 as a hole transport layer material.

[ Evaluation example 6]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices manufactured in Examples 163 to 192 and Comparative Example 6, and the results are shown in Table 6 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 163 Cpd1 4.1 22.2 Example 164 Cpd3 4.3 20.1 Example 165 Cpd4 4.4 21.3 Example 166 Cpd5 4.0 22.6 Example 167 Cpd9 4.5 19.5 Example 168 Cpd13 4.7 20.1 Example 169 Cpd15 4.3 21.6 Example 170 Cpd16 4.5 20.5 Example 171 Cpd17 4.7 20.6 Example 172 Cpd21 4.4 21.6 Example 173 Cpd25 5.0 20.1 Example 174 Cpd27 5.1 18.6 Example 175 Cpd28 4.3 22.0 Example 176 Cpd29 4.6 21.2 Example 177 Cpd32 4.5 21.2 Example 178 Cpd34 4.4 22.3 Example 179 Cpd36 5.2 18.1 Example 180 Cpd37 5.0 18.9 Example 181 Cpd38 4.5 21.7 Example 182 Cpd41 4.7 21.2 Example 183 Cpd43 4.8 20.8 Example 184 Cpd45 4.5 21.4 Example 185 Cpd46 5.1 18.2 Example 186 Cpd47 5.1 18.5 Example 187 Cpd50 4.3 22.3 Example 188 Cpd52 4.6 21.4 Example 189 Cpd54 4.8 21.6 Example 190 Cpd55 4.2 22.5 Example 191 Cpd56 4.7 20.6 Example 192 Cpd59 4.6 20.2 Comparative Example 6 NPB 5.2 18.1

As shown in Table 6, in the case of Examples 163 to 192 in which the compound (Cpd1 to Cpd59) represented by the formula (1) according to the present invention was used as a hole transport layer, the organic electroluminescent device using Comparative Example 6 In comparison, it can be seen that performance is better in terms of efficiency and driving voltage.

[ Example 193] Blue organic Field Fabrication of light emitting device

The compound Cpd65 was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was produced as follows.

(15 nm) / AND + 5% DS-405 (30 nm) / Compound Cpd86 (5 nm) / Alq ₃ (25 nm) / LiF 1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

[ Example 194 ~ 228] Blue organic Field Fabrication of light emitting device

A blue organic electroluminescent device was manufactured in the same manner as in Example 193 except that each compound described in Table 7 was used in place of the compound Cpd65 used as an electron transporting auxiliary layer material in Example 193.

[ Comparative Example 7] Blue organic Field Fabrication of light emitting device

It does not include the secondary electron transporting layer, and is performed in the same manner as in Example 193 except that the electron transporting material Alq ₃ is deposited to 30nm instead of 25 nm to prepare a blue organic light emitting element.

[ Comparative Example 8] Blue organic Field Fabrication of light emitting device

An organic electroluminescent device was fabricated in the same manner as in Example 193 except that BCP was used instead of the compound compound Cpd65 used as the electron transporting auxiliary layer material in Example 193.

The structure of the BCP used is as follows.

[ Evaluation example 7]

The driving voltage, current efficiency, emission wavelength and lifetime (T97) at current densities of 10 mA / cm 2 were measured for the organic electroluminescent devices prepared in Examples 193 to 228 and Comparative Examples 7 and 8, respectively, Table 7 shows the results.

Sample Electron transporting auxiliary layer Driving voltage
(V) Current efficiency
(cd / A) Emission peak
(nm) life span
(hr, T ₉₇ ) Example 193 Cpd65 4.4 6.2 457 45 Example 194 Cpd69 4.1 6.3 458 62 Example 195 Cpd73 4.2 6.6 458 55 Example 196 Cpd76 4.5 6.2 458 75 Example 197 Cpd79 4.3 6.5 458 59 Example 198 Cpd80 4.3 6.1 458 78 Example 199 Cpd81 4.4 6.4 457 60 Example 200 Cpd82 4.1 6.2 458 64 Example 201 Cpd83 4.7 6.0 458 50 Example 202 Cpd107 4.7 6.4 457 85 Example 203 Cpd111 4.5 6.1 458 55 Example 204 Cpd115 4.4 6.0 458 75 Example 205 Cpd118 4.1 6.3 458 62 Example 206 Cpd121 4.2 6.6 458 55 Example 207 Cpd122 4.5 6.2 458 75 Example 208 Cpd123 4.3 6.4 457 60 Example 209 Cpd124 4.4 6.2 458 64 Example 210 Cpd125 4.1 6.0 458 50 Example 211 Cpd148 4.2 6.4 457 85 Example 212 Cpd152 4.4 6.1 458 55 Example 213 Cpd156 4.1 6.0 458 75 Example 214 Cpd159 4.7 6.3 458 62 Example 215 Cpd162 4.7 6.4 457 60 Example 216 Cpd163 4.5 6.2 458 64 Example 217 Cpd164 4.4 6.0 458 50 Example 218 Cpd165 4.1 6.4 457 85 Example 219 Cpd166 4.7 6.1 458 55 Example 220 Cpd189 4.7 6.0 458 75 Example 221 Cpd193 4.5 6.3 458 62 Example 222 Cpd197 4.4 6.6 458 55 Example 223 Cpd200 4.1 6.2 458 75 Example 224 Cpd203 4.2 6.4 457 60 Example 225 Cpd204 4.5 6.2 458 64 Example 226 Cpd205 4.3 6.0 458 50 Example 227 Cpd206 4.1 6.4 457 85 Example 228 Cpd207 4.2 6.1 458 55 Comparative Example 7 _ 4.7 5.6 458 32 Comparative Example 8 BCP 5.3 5.9 458 28

As can be seen from Table 7, in the case of the blue organic electroluminescent devices of Examples 193 to 228 in which the compounds Cpd65 to 207 synthesized in Synthesis Examples 59 to 118 were used as the electron transporting auxiliary layer material, the electron transporting auxiliary layer was not used The driving voltage was similar to or slightly superior to that of the blue organic electroluminescent device of Comparative Example 7, but the current efficiency and lifetime were greatly improved.

In addition, as compared with the blue organic electroluminescent device of Comparative Example 8 in which a conventional BCP was used as an electron transporting auxiliary layer material in place of the electron transporting auxiliary layer, not only the driving voltage and the current efficiency were excellent, but also the lifetime was remarkably improved.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It is natural.

Claims

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

In Formula 1,
X ₁ and X ₂ are each independently selected from the group consisting of O, S, N (R ₄ ) and C (R ₅ ) (R ₆ );
L ₁ to L ₃ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
R ₁ and R ₄ to R ₆ are each independently 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 ~ 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, 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, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ tile to selected or adjacent from the group consisting of an aryl amine of the C ₆₀ combined to form a condensed ring, and , When a plurality of each of R ₄ to R ₆ is present, they are the same as or different from each other;
m and n are each independently an integer of 0 to 4;
R ₂ and R ₃ are each independently selected from deuterium, halogen, cyano group, 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 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 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 an aryl phosphine group, and groups binding to selected or adjacent from the group consisting of C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ with an aryl amine of the C ₆₀ to which they are attached may form a fused ring, wherein R ₂ and R ₃ are the same or different from each other;
Wherein L ₁ to the aryl group and a hetero arylene group, R ₁ to an alkyl group R ₆ in the L _3, 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 boron group, an aryl phosphine group, a mono- or diaryl phosphine blood group and an aryl silyl group each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ 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 alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine group, a C ₆ to C ₆₀ mono or diarylphosphinyl group, and a C ₆ to C _{6 0 &lt}; / RTI > arylsilyl group, and when they are substituted with a plurality of substituents, they may be the same or different.

The method according to claim 1,
Wherein the compound represented by Formula 1 is a compound represented by any one of Chemical Formulas 2 to 7:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 2 to 7,
m, n, R ₁ to R ₄ and L ₁ to L ₃ are each as defined in claim 1.

The method according to claim 1,
Wherein L ₁ to L ₃ are each independently a linker represented by any one of the following formulas (8) to (13):
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above Formulas 8 to 13,
* Denotes the part where the bond is made;
Y ₁ is O, S or N (R ₈ );
Y ₂ is O, S, N (R ₈ ) or C (R ₉ ) (R ₁₀ );
Y ₃ is N or C (R ₁₁ );
l is an integer from 0 to 4;
R ₇ is heavy hydrogen, 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 ₆ ~ C ₆₀ aryl group, the nucleus of atoms of A C ₆ to C ₆₀ alkyloxy group, a C ₃ to C ₄₀ cycloalkyl group, a heteroaryloxy group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ heteroaryl group, a C ₆ to C ₆₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, C ₆ to C ₆₀ arylamine groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ arylphosphine groups, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent, may form a condensed ring, when the R ₇ plurality personal they each other Identical or different;
R ₈ to R ₁₁ 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 ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting of C ₆₀ of arylsilyl, by combining groups of adjacent, may form a condensed ring;
Alkyl group of the R ₇ to R _11, 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 substituted or unsubstituted aryl group, ~ 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 ~ arylamine group of C _60, 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 ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, 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 one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

The method of claim 3,
Wherein R ₇ is selected from the group consisting of deuterium, halogen, cyano, C ₁ to C ₄₀ alkyl, C ₆ to C ₆₀ aryl, and a heteroaryl group having 5 to 60 ring atoms.

The method according to claim 1,
Wherein R < ₁ > is a substituent represented by any one of the following formulas (14) to (20)
[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

In the above formulas 14 to 20,
* Means the part where the bond is made:
p and q are each independently an integer of 0 to 4;
Z ₁ to Z ₁₂ are each independently N or C (R ₁₄ );
Any one of Z ₁ to Z ₄ bonded to L ₃ in the above formulas 15 and 19 is C (R ₁₄ ), in which case R ₁₄ is a member;
T ₁ and T ₂ are each independently selected from the group consisting of a single bond, C (R ₁₅ ) (R ₁₆ ), N (R ₁₇ ), O and S, but not both T ₁ and T ₂ are single bonds;
R ₁₂ and R ₁₃ are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ alkynyl group of C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of, C ₆ ~ C ₆₀ the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of _{C 6 ~ C 60, C 1} ~ C 40 alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 C ₆ to C ₆₀ arylamino groups, C ₁ to C ₄₀ alkylsilyl groups, C ₁ to C ₄₀ alkylboron groups, C ₆ to C ₆₀ arylboron groups, C ₆ to C ₆₀ an aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from an aryl silyl group the group consisting of C _60, the combined group and adjacent to which they are attached may form a fused ring, wherein R ₁₂ And R < ₁₃ > each are the same or different from each other;
R ₁₄ to R ₁₇ each independently represent 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 ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from an aryl silyl group the group consisting of C _60, the combined group and adjacent to which they are attached may form a fused ring, wherein When there are plural R ₁₄ to R ₁₇ each, these are the same or different from each other;
Alkyl group of said R ₁₂ to R _17, 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 substituted or unsubstituted aryl group, ~ 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 ~ arylamine group of C _60, 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 ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, 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 one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

The method according to claim 1,
Wherein R ₁ is a substituent to a compound represented by any one of Formula A-1 to A-24:

In the above Formulas A-1 to A-24,
* Denotes the part where the bond is made,
t is an integer from 0 to 5;
l is an integer from 0 to 4;
v is an integer from 0 to 3;
u is an integer from 0 to 2;
p and q are each independently an integer of 0 to 4;
R _12, R ₁₃ and R ₁₈ is a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl groups, C ₆ each independently represent a deuterium, a halogen, a cyano group, ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C ₆₀ aryloxy group, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C of ₆ ~ C ₆₀ aryl amine group, C ₁ ~ alkyl silyl group of C _40, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of C ₆ ~ C _60, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from the group consisting arylsilyl of C _60, the combined group and adjacent, may form a condensed ring, When there are a plurality of R ₁₂ , R ₁₃ and R ₁₈ each, they are the same as or different from each other;
R ₁₄ to R ₁₇ each independently represent 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 ₆ ~ of C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~, or selected from an aryl silyl group the group consisting of C _60, the combined group and adjacent to which they are attached may form a fused ring, wherein When a plurality of R < ₁₄ > s are the same or different from each other;
Alkyl group of said R ₁₂ to R _18, 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 substituted or unsubstituted aryl group, ~ 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 ~ arylamine group of C _60, 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 ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group of, 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 one substituent or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

The method according to claim 1,
Wherein R < ₁ _> is a substituent represented by the following formula (21):
[Chemical Formula 21]

In Formula 21,
* Means the part where the bond is made:
R ₁₉ and R ₂₀ 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 ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ aryloxy C _60, C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ aryl of C ₆₀ amine group, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, an aryl boronic of _{C 6 ~ C 60, C 6} ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood group and a C ₆ ~ C ₆₀ aryl silyl group selected from the group consisting of, or combine tile adjacent to form a condensed ring;
Alkyl group of said R ₁₉ and R _20, 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 substituted or unsubstituted aryl group, ~ 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 ~ arylamine group of C _60, 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 ~ alkyl boron C ₄₀ of the group, C ₆ ~ for C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, one selected from the group consisting of a C ₆ ~ C ₆₀ aryl silyl mono- or diaryl phosphine blood group and C ₆ ~ C ₆₀ of the And when they are substituted with a plurality of substituents, they may be the same or different from each other.

8. The method of claim 7,
Each of R ₁₉ and R ₂₀ 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 method according to claim 1,
Wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds:

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).

11. The method of claim 10,
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.