KR20170016703A - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound having excellent light emitting abilities and an organic electroluminescent device comprising the same in one or more organic layers and having improved properties such as light emitting efficiency, driving voltage, lifespan, etc. To this end, the compound of the present invention is represented by chemical formula 1.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the same. BACKGROUND ART [0002]

The present invention relates to a novel organic luminescent compound and an organic electroluminescent device using the same. More particularly, the present invention relates to a novel xanthene, thioxanthene or acridine-based compound having excellent hole injection and transport ability, Organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage and lifetime.

A study on the electroluminescent (EL) device (organic EL device) that led to the blue electroluminescence using the anthracene single crystal in 1965 based on the observation of the organic thin film emission of the Bernanose in the 1950s, And a functional layer of a light-emitting layer. In order to manufacture a high efficiency and high number of organic electroluminescent devices, the organic electroluminescent device has developed into a form in which each characteristic organic layer in the device is introduced, leading to the development of specialized materials used therefor.

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

The light emitting layer forming material of the organic electroluminescent device can be classified into blue, green and red light emitting materials according to the luminescent color. In addition, yellow and orange light emitting materials are also used as light emitting materials for realizing better color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of such a phosphorescent material can theoretically improve luminous efficiency up to four times that of fluorescence, and attention is focused on phosphorescent host materials as well as phosphorescent dopants.

Up to now, hole injecting layer, hole transporting layer. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq ₃ and the like represented by the following formulas are widely known. Anthracene derivatives as a light emitting material have been reported as a fluorescent dopant / host material. Particularly, as a phosphorescent material having a great advantage in improving the efficiency of a light emitting material, a metal complex compound containing Ir such as Firpic, Ir (ppy) ₃ , (acac) Ir (btp) ₂ and the like is used as a blue, green and red dopant material . So far, CBP has shown excellent properties as a phosphorescent host material.

However, existing materials have advantages in terms of light emitting properties, but they have low glass transition temperature and poor thermal stability, which is not satisfactory in terms of lifetime in an organic electroluminescent device.

It is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and has excellent hole injecting, transporting ability and light emitting ability.

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

In order to accomplish the above object, the present invention provides a compound represented by the following Formula 1:

[Chemical Formula 1]

(2)

In the above formulas (1) and (2)

At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ is condensed with the ring represented by Formula 2 to form a condensed ring;

The dotted line is the part where the condensation occurs;

X ₁ and X ₂ are each independently O, S, Se, N ( Ar 3), C (Ar 4) (Ar 5) and Si (Ar ₆₎ is selected from the group consisting of (Ar _7), wherein X ₂ Lt; / RTI > are the same or different;

A ₁ to A ₈ are each independently N or C (R ₅ );

And R ₁ to R ₄ do not form a ring and a condensed ring represented by the formula 2, R ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ an alkenyl group of C _40, C ₂ ~ C ₄₀ of the alkynyl group, 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 of the C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ aryl groups, alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ And each adjacent R ₅ may combine with each other to form a condensed ring. When a plurality of R _{5 s} are present, they may be the same or different;

Ar ₁ to Ar ₇ each independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, C ₆ to C ₆₀ aryloxy groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ aryl groups, An arylsilyl group of C ₆ to C ₆₀ , 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 A mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, or Ar ₁ and Ar ₂ may combine with each other to form a condensed ring, and Ar ₂ to Ar ₆ When there are a plurality of each of them, they are the same as or different from each other;

The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group of R ₁ to R ₅ and Ar ₁ to Ar ₇ A boron group, an arylphosphine group, a mono or diarylphosphinyl group, and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ alkynyl group, ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C substituted with at least ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl amine of the selected one or more substituents being unsubstituted, When substituted with a plurality of substituents, they may be the same or different.

The present invention also provides an organic electroluminescent device comprising (i) a positive electrode, (ii) a negative electrode, and (iii) at least one organic material layer interposed between the positive electrode and the negative electrode, One is an organic electroluminescent device comprising a compound represented by the general formula (1).

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

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

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

"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, a form in which two or more rings are pendant or condensed with each other may be included, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

In the present invention, "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.

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

"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 carbon of the ring, preferably 1 to 3 carbons, Or < RTI ID = 0.0 > Se. ≪ / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

In the present invention, "alkylsilyl" 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.

The compound represented by the general formula (1) of the present invention has excellent thermal stability and luminescent properties and can be used as a material of an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, it is possible to produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency, and long life time, A full color display panel having improved performance and lifetime can be manufactured.

Hereinafter, the present invention will be described in detail.

1. New organic compounds

A 5-membered heteroaromatic ring moiety condensed with xanthene, thioxanthene and acridine benzene, an indene moiety, or an indole moiety is condensed to form a basic skeleton, . The compound represented by the formula (1) has a higher molecular weight than the conventional organic electroluminescence device material (for example, 4,4-dicarbazolylbiphenyl (hereinafter referred to as 'CBP')) Not only the stability is excellent but also the carrier transporting ability and the light emitting ability are excellent. Accordingly, when an organic electroluminescent device includes a compound represented by the following formula (1), the driving voltage, efficiency, lifetime, etc. of the device can be improved.

Specifically, the compound represented by the formula (1) is as follows:

[Chemical Formula 1]

(2)

In the above formulas (1) and (2)

At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ is condensed with the ring represented by Formula 2 to form a condensed ring;

The dotted line is the part where the condensation occurs;

X ₁ and X ₂ are each independently O, S, Se, N ( Ar 3), C (Ar 4) (Ar 5) and Si (Ar ₆₎ is selected from the group consisting of (Ar _7), wherein X ₂ Lt; / RTI > are the same or different;

A ₁ to A ₈ are each independently N or C (R ₅ );

And R ₁ to R ₄ do not form a ring and a condensed ring represented by the formula 2, R ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ an alkenyl group of C _40, C ₂ ~ C ₄₀ of the alkynyl group, 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 of the C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ aryl groups, alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ And each adjacent R ₅ may combine with each other to form a condensed ring. When a plurality of R _{5 s} are present, they may be the same or different;

Ar ₁ to Ar ₇ each independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, C ₆ to C ₆₀ aryloxy groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ aryl groups, An arylsilyl group of C ₆ to C ₆₀ , 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 A mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, or Ar ₁ and Ar ₂ may combine with each other to form a condensed ring, and Ar ₃ to Ar ₇ When there are a plurality of each of them, they are the same as or different from each other;

The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group of R ₁ to R ₅ and Ar ₁ to Ar ₇ A boron group, an arylphosphine group, a mono or diarylphosphinyl group, and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ alkynyl group, ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C substituted with at least ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl amine of the selected one or more substituents being unsubstituted, When substituted with a plurality of substituents, they may be the same or different.

Generally, in a phosphorescent light emitting layer of an organic electroluminescent device, the host material should have a triplet energy gap higher than the triplet energy gap of the dopant. That is, when the lowest excitation state of the host is higher in energy than the lowest emission state of the dopant, the phosphorescence efficiency can be improved. The compound of Formula 1 has a high triplet energy and a specific substituent is introduced into a basic skeleton in which an indole derivative having a broad singlet energy level and a high triplet energy level is condensed so that the energy level can be controlled to be higher than that of the dopant And can be used as a host material.

Further, since the compound of the present invention has a high triplet energy as described above, it is possible to prevent the excitons generated in the light emitting layer from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer. Therefore, when an organic layer (hereinafter, referred to as 'light emission-assisting layer') is formed between the hole transporting layer and the light emitting layer using the compound of Formula 1, the diffusion of the excitons is prevented by the compound, Unlike the conventional organic electroluminescent device not including the blocking 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. Also, when an organic material layer (hereinafter, referred to as a 'life improving layer') is formed between the light emitting layer and the electron transporting layer by using the compound of Formula 1, the diffusion of the exciton is prevented by the compound of Formula 1, The durability and stability of the light emitting element can be improved, and the half life of the element can be efficiently increased. Thus, the compound represented by the formula (1) may be used as a light-emitting auxiliary layer material or a life improving layer material other than the host of the light emitting layer.

In addition, the compound of Formula 1 can control the HOMO and LUMO energy levels according to the type of the substituent introduced into the basic skeleton, and can have a wide band gap and a high carrier transporting property. For example, when the electron donating group (EWG) having a high electron absorbing property such as a nitrogen-containing heterocycle (for example, a pyridine group, a pyrimidine group, a triazine group, etc.) is bonded to the basic skeleton, Since it has the property of bipolar, the bonding force between holes and electrons can be increased. As described above, the compound of Formula 1 in which EWG is introduced into the basic skeleton has excellent carrier transporting property and light emitting property. Therefore, the compound of Formula 1 can be used as an electron injection / transport layer material or a life improving layer material other than the light emitting layer material of the organic electroluminescence device Can be used. On the other hand, when the electron donor compound (EDG) is bonded to the basic skeleton of the compound of Formula 1 such as an arylamine group, a carbazole group, a terphenyl group, a triphenylene group, etc., , It can be usefully used as a hole injecting / transporting layer or a light emitting auxiliary layer material other than the light emitting layer material.

As described above, the compound represented by Formula 1 can improve the luminescent characteristics of the organic electroluminescent device and improve the hole injecting / transporting ability, the electron injecting / transporting ability, the light emitting efficiency, the driving voltage, . Accordingly, the compound of formula (I) according to the present invention is useful as an organic electroluminescent device, preferably an organic layer material, preferably a light emitting layer material (blue, green and / or red phosphorescent host material), an electron transport / injection layer material and a hole transport / Emitting layer material, a light-emitting auxiliary layer material, a life-improving layer material, and more preferably a light-emitting layer material, an electron injection layer material, a light-

In addition, the compound of formula (1) may have various substituents, especially an aryl group and / or a heteroaryl group, introduced into the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, And may have a higher thermal stability than the material (e.g., CBP). The compound represented by the above formula (1) is also effective for inhibiting crystallization of the organic material layer. Accordingly, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifetime characteristics, and the full-color organic luminescent panel to which such an organic electroluminescent device is applied can also maximize the performance.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by any one of Chemical Formulas 3 to 8:

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above Chemical Formulas 3 to 8,

X ₁ , X ₂ , Ar ₁ , Ar ₂ and A ₁ to A ₈ are the same as defined in the above formulas (1) and (2).

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by Formula 9:

[Chemical Formula 9]

(2)

In the above formulas (2) and (9)

At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ is condensed with the ring represented by Formula 2 to form a condensed ring;

The dotted line is the part where the condensation occurs;

X ₁ and X ₂ are each independently O, S, Se, N ( Ar 3), C (Ar 4) (Ar 5) and Si (Ar ₆₎ is selected from the group consisting of (Ar _7), wherein X ₂ Lt; / RTI > are the same or different;

A ₁ to A ₁₃ are each independently N or C (R ₅ );

And R ₁ to R ₄ do not form a ring and a condensed ring represented by the formula 2, R ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ an alkenyl group of C _40, C ₂ ~ C ₄₀ of the alkynyl group, 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 of the C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ aryl groups, alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ And each adjacent R ₅ may combine with each other to form a condensed ring. When a plurality of R _{5 s} are present, they may be the same or different;

Ar ₁ and Ar ₃ to Ar ₇ each independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, an aryloxy group of a C ₆ ~ C _60, C ₃ -aryl silyl group of C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ of, C ₁ - C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine group, C ₆ of the C ₆₀ mono-or diaryl phosphine of C ₆₀ P is selected from the group the group consisting of C ₆ - C ₆₀ aryl amine, wherein Ar ₃ to Ar ₇ When there are a plurality of each of them, they are the same as or different from each other;

The R ₁ to R ₅ , Ar ₁ And an alkyl group of Ar ₃ to Ar ₇ , a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, , The mono or diarylphosphinyl group and the arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ aryl amine, or unsubstituted, and the plurality of substitution Case be substituted with these may be the same or different from each other.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound represented by Formula 10:

[Chemical formula 10]

(2)

In the above formulas (2) and (10)

At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ is condensed with the ring represented by Formula 2 to form a condensed ring;

The dotted line is the part where the condensation occurs;

X ₁ and X ₂ are each independently O, S, Se, N ( Ar 3), C (Ar 4) (Ar 5) and Si (Ar ₆₎ is selected from the group consisting of (Ar _7), wherein X ₂ Lt; / RTI > are the same or different;

A ₁ to A ₈ and A ₁₄ to A ₂₁ are each independently N or C (R ₅ );

And R ₁ to R ₄ do not form a ring and a condensed ring represented by the formula 2, R ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ an alkenyl group of C _40, C ₂ ~ C ₄₀ of the alkynyl group, 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 of the C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ aryl groups, alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ And each adjacent R ₅ may combine with each other to form a condensed ring. When a plurality of R _{5 s} are present, they may be the same or different;

Ar ₃ to Ar ₇ each independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, C ₆ to C ₆₀ aryloxy groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ aryl groups, An arylsilyl group of C ₆ to C ₆₀ , 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 A mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, and Ar ₃ to Ar ₇ When there are a plurality of each of them, they are the same as or different from each other;

The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group and aryl group of R ₁ to R ₅ and Ar ₃ to Ar ₇ A boron group, an arylphosphine group, a mono or diarylphosphinyl group, and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ alkynyl group, ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C substituted with at least ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl amine of the selected one or more substituents being unsubstituted, When substituted with a plurality of substituents, they may be the same or different.

According to a preferred embodiment of the present invention, in the compound represented by Formula 1, X ₁ and X ₂ may each independently be selected from the group consisting of O, S, and N (Ar ₃ ).

According to a preferred embodiment of the present invention, in the compound represented by Formula 1, Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C be an aryl group and a nuclear atoms unsubstituted or substituted with of ₆₀ 5 to 60 heteroatoms, or selected from the aryl group the group consisting of, wherein Ar ₁ and the Ar ₂ are bonded to each other substituted or unsubstituted C ₆ ~ fused ring of C ₆₀ Can be formed.

According to a preferred embodiment of the present invention, in the compound represented by Formula 1, Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, and a substituted or unsubstituted phenyl group Or Ar ₁ and Ar ₂ may be bonded to each other to form a fluorene structure.

According to a preferred embodiment of the present invention, in the compound represented by the general formula (1), Ar ₃ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted 5- to 60- Lt; / RTI >

According to a preferred embodiment of the present invention, in the compound represented by Formula 1, Ar ₃ is an aryl group having ₆ to ₆₀ carbon atoms or a heteroaryl group having 5 to 60 nuclear atoms,

The aryl group and the heteroaryl group are each independently substituted with at least one substituent selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, And when they are substituted with a plurality of substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, in the compound represented by the general formula (1), Ar ₃ may be selected from the group consisting of phenyl, biphenyl and fluorene,

The phenyl, biphenyl and fluorene are each independently substituted with at least one substituent selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 ring atoms Which are unsubstituted and substituted with a plurality of substituents, may be the same or different from each other.

According to a preferred embodiment of the present invention, in the compound represented by the general formula (1), Ar ₃ may be selected from the group consisting of phenyl, biphenyl and fluorene,

Wherein the phenyl, biphenyl and fluorene are each independently substituted with at least one substituent selected from the group consisting of a methyl group, an ethyl group, a phenyl group, a biphenyl group, a triphenylene group, an imidazolyl group, a carbazolyl group and a dibenzothiophenyl group And when they are unsubstituted and substituted with a plurality of substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, at least one of R ₅ and Ar ₁ to Ar ₇ , preferably Ar ₁ and Ar ₂ , in the compound represented by Formula 1 is represented by Formula 11 A substituent or a phenyl group.

(11)

In Formula 11,

* Means a moiety bonded to Formula 1 or Formula 2;

L ₁ is selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group and a nuclear atoms of 5 to 18 groups heteroarylene, preferably a single bond, phenylene group, biphenyl group or a carbazolyl group;

Z ₁ to Z ₅ are each independently N or C (R ₆ ), or at least one of Z ₁ to Z ₅ is N;

R ₆ is 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 ~ C ₆₀ of the aryl group, 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 number of nuclear atoms of 3 to 40 heterocycloalkyl group , An arylamine group of C ₆ to C ₆₀ , 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 , C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ C ₆₀ selected from the group consisting arylsilyl or in, or adjacent groups of (e.g., L, the other R ₁₁ which are adjacent) in combination with a condensed ring And when a plurality of R < ₆ > s are present, they may be the same or different from each other;

Arylene group and a heteroarylene group, an alkyl group of the R ₆ of said L _1, 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, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the 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 ~ C _A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl yarn And when they are substituted with a plurality of substituents, they may be the same as or different from each other.

According to a preferred embodiment of the present invention, in the substituent represented by the general formula (11), R ₆ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 60 hetero atoms Lt; / RTI >

According to a preferred embodiment of the present invention, in the substituent represented by the general formula (11), R ₆ may be a phenyl group or a biphenyl group,

The phenyl group and the biphenyl group of R ₆ are substituted or unsubstituted with at least one substituent selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms , 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, examples of the substituent represented by the formula (11) include substituents represented by the following A-1 to A-15, but are not limited thereto.

In the above A-1 to A-15,

n is an integer of 0 to 4, and when n is 0, hydrogen means that hydrogen is not substituted with substituent R ₇ ; when n is an integer of 1 to 4, R ₇ is deuterium, halogen, cyano, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, C ₆ of ~ 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 arylamine group of ₆ ~ C _60, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, 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 selected from an aryl silyl group the group consisting of or of, by combining together with the adjacent group (e. g., such as L _1, R ₆ or another R ₇₎ to which they are attached may form a fused ring, wherein R ₇ plurality If they are individuals, And one or different,

Alkyl group of the R _7, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy 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,

*, L ₁ and R ₆ are as defined in the above formula (11).

According to a preferred embodiment of the present invention, at least one of R ₅ and Ar ₁ to Ar ₇ in the compound represented by Formula 1 may be a substituent represented by Formula 12 below.

[Chemical Formula 12]

In Formula 12,

* Means a moiety bonded to Formula 1 or Formula 2;

L ₂ is a single bond, C ₆ ~ be an aryl group and a nucleus of atoms of C ₁₈ is selected from 5 to 18 heteroarylene group consisting, preferably a single bond, phenylene group, biphenyl group or a carbazolyl group;

R ₈ and R ₉ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine group Or R ₈ and R ₉ may combine to form a condensed ring;

Wherein the L ₂ arylene group and a heteroarylene group, wherein R ₈ and a group of R _9, an aryl group, a heteroaryl group, and aryl amine groups are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ 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 ~ C ₆₀ of the Arylsilyl group, 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, in the substituent represented by the general formula (12), R ₈ and R ₉ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted nuclear atom And can be from 5 to 60 heteroaryl groups.

According to a preferred embodiment of the present invention, in the substituent represented by the general formula (12), R ₈ and R ₉ each independently represent a phenyl group, a biphenyl group or a fluorenyl group,

The phenyl group, biphenyl group and fluorenyl group of R ₈ and R ₉ may be substituted with at least one selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms And when they are substituted with a plurality of substituents, they may be the same or different.

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 synthesis method. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

2. Organic electroluminescent device

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.

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

The at least one organic material layer may include at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. have. Specifically, the organic material layer containing the compound of Formula 1 is preferably a light emitting layer, an electron transporting layer, or a hole transporting layer.

The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as a host material. The light emitting layer of the organic electroluminescent device of the present invention may include a compound other than the compound of Formula 1 as a host.

The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting layer and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting auxiliary layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include the compound represented by Formula 1, and preferably includes a hole transporting layer, The auxiliary layer may include a compound represented by the above formula (1). On the other hand, an electron injection layer may be further stacked on the electron transport layer.

The structure of the organic electroluminescent device of the present invention may be a structure in which an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic layer.

The organic electroluminescent device of the present invention can be produced by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).

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

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

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); 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.

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

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

[ Preparation Example  One]

1. Synthesis of a-1 (2- bromo- 9- methyl - 9 - phenyl-9H-xanthene)

Under nitrogen gas stream, 1-bromo-2- (4-bromophenoxy) benzene (50 g, 152 mmol), 2- acetophenone (36.5 g, 304 mmol), Pd (PPh 3) 4, triflic acid (0.6 g, 304 mmol) and 140 ml of toluene, and the mixture was stirred at 100 ° C for 36 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and 44.8 g (84%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 350.03 g / mol, measured: 351.24 g / mol)

^{1 H-NMR: δ 7.56 (} d, 1H), 7.3 ~ 7.17 (m, 9H), 7.01 (m, 1H), 2.3 (s, 3H)

2. Synthesis of a-2 (9- methyl -2- (2 -nitrophenyl ) -9-phenyl-9H-xanthene)

(44 g, 124 mmol), (2-nitrophenyl) boronic acid (23 g, 137 mmol), K ₂ CO ₃ (42.8 g, 310 mmol) Pd (PPh 3) 4 (7.16 g, 6.2 mmol) and 200 ml / 40 ml of toluene / H ₂ O were added, and the mixture was stirred at 100 ° C for 8 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 38 g (78%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 393.14 g / mol, measured: 393.44 g / mol)

¹ H-NMR:? 8.03 (m, 2H), 7.89 (t, IH), 7.76 (m, 2H), 7.57 (d, 2.2 (s, 3H)

3. a-3 (13- methyl-13-phenyl-chroman Agate -12,13- dihydro [3,2-a] carbazole) Synthesis of

(54 g, 88.9 mmol), PPh ₃ (70 g, 266.8 mmol) and 200 ml of nitrobenzene were placed under a nitrogen stream and refluxed for 8 hours Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and then subjected to column chromatography to obtain 26 g (82%) of the target compound.

GC-Mass (calculated: 361.15 g / mol, measured: 361.44 g / mol)

⁽ M, 1H), 7.59 (d, IH), 7.59 (d, IH) 7.2 (m, 10 H), 7.01 (m, 1 H), 2.25 (s, 3 H)

[ Preparation Example  2] 13- methyl -13-phenyl-11,13- Dihydrochromeno [3,2-b] carbazole  synthesis

The procedure of Preparation Example 1 was repeated except that 1-bromo-2- (3-bromophenoxy) benzene was used as a reactant to obtain 15 g of the target compound.

GC-Mass (calculated: 361.15 g / mol, measured: 361.44 g / mol)

[ Preparation Example  3] 8- methyl -8-phenyl-5,8- Dihydrochromeno [3,2-c] carbazole  synthesis

The procedure of Preparation Example 1 was repeated, except that 2,2'-oxybis (bromobenzene) was used as a reactant, to obtain 10 g of the target compound.

 GC-Mass (calculated: 361.15 g / mol, measured: 361.44 g / mol)

[ Preparation Example  4]

1. Synthesis of b-1 (N- (2- bromophenyl) -9-methyl-9-phenyl -9H- xanthene-4-amine)

250 mL of xylene was added to 50 g (142.3 mmol) of 4-bromo-9-methyl-9-phenyl-9H-xanthan and 26.9 g (156.5 mmol) of 2-bromoaniline under a nitrogen stream. 3.9 g (4.269 mmol) of Pd ₂ (dba) ₃ , ₄ g (8.53 mmol) of Xphos and 34 g (355 mol) of NaOtBu were added and the mixture was refluxed at 120 ° C for 24 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of an aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure and purified by silica gel column chromatography to obtain 49 g of the target compound (yield 78%).

GC-Mass (theory: 441.07 g / mol, measured: 442.36 g / mol)

¹ H-NMR:? 9.94 (br, IH), 7.66 (d, IH), 7.69 ~ 7.17 (m,

2. b-2: Synthesis of (7-methyl-7-phenyl -7,13- dihydro-chroman Agate [2,3-a] carbazole)

(49 g, 110 mmol), K ₂ OAc (16 g, 166 mmol) and Pd (2-bromophenyl) -9- PPh ₃ ) ₄ (5 g, 4.4 mmol) and 200 ml of DMF, and the mixture was stirred at 100 DEG C for 8 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 38 g (78%) of the target compound was obtained by column chromatography.

GC-Mass (calculated: 361.15 g / mol, measured: 361.44 g / mol)

⁽ M, 1H), 7.59 (d, IH), 7.59 (d, IH) 7.2 (m, 10 H), 7.01 (m, 1 H), 2.25 (s, 3 H)

[ Preparation Example  5] 13- methyl -13-phenyl-7, 13- Dihydrochloreno [2,3-b] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 3-bromo-9-methyl-9-phenyl-9H-xanthene was used as a reactant, to obtain 18 g of the title compound;

 GC-Mass (calculated: 361.15 g / mol, measured: 361.44 g / mol)

[ Preparation Example  6] 13- methyl -13-phenyl-8,13- Dihydrochloreno [2,3-c] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 2-bromo-9-methyl-9-phenyl-9H-xanthene obtained in Step 1 of Preparation Example 1 was used as a reactant to obtain 18 g of the title compound.

 GC-Mass (calculated: 361.15 g / mol, measured: 361.44 g / mol)

[ Preparation Example  7] 13- methyl -13-phenyl-12,13- Dihydrothiochromeno [3,2-a] carbazole  synthesis

The procedure of Preparation Example 1 was repeated, except that (2-bromophenyl) (4-bromophenyl) sulfoxide and acetophenone were used as reactants to obtain 11 g of the title compound;

GC-Mass (theory: 377.12 g / mol, measurement: 377.51 g / mol)

[ Preparation Example  8] 13- methyl -13-phenyl-11,13- Dihydrothiochromeno [3,2-b] carbazole  synthesis

The procedure of Preparation Example 1 was repeated, except that (2-bromophenyl) (3-bromophenyl) sulfoxide and acetophenone were used as a reaction product to obtain 12 g of the desired compound;

GC-Mass (theory: 377.12 g / mol, measurement: 377.51 g / mol)

[ Preparation Example  9] 8- methyl -8-phenyl-5,8- Dihydrochromeno [3,2-c] carbazole  synthesis

The procedure of Preparation Example 1 was repeated, except that bis (2-bromophenyl) sulfoxide and acetophenone were used as reactants to obtain 9 g of the target compound.

GC-Mass (theory: 377.12 g / mol, measurement: 377.51 g / mol)

[ Preparation Example  10] 7- methyl -7-phenyl-7,13- Dihydrothiochromeno [2,3-a] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 4-bromo-9-methyl-9-phenyl-9H-thioxanthin of Preparation Example 9 was used as a reactant to obtain 12 g of the title compound.

 GC-Mass (theory: 377.12 g / mol, measurement: 377.51 g / mol)

[ Preparation Example  11] 13- methyl -13-phenyl-7, 13- Dihydrothiochromeno [2,3-b] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 3-bromo-9-methyl-9-phenyl-9H-thioxanthine of Preparation Example 8 was used as a reactant to obtain 11 g of the title compound;

 GC-Mass (theory: 377.12 g / mol, measurement: 377.51 g / mol)

[ Preparation Example  12] 13- methyl -13-phenyl-8,13- Dihydrothiochromeno [2,3-c] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 2-bromo-9-methyl-9-phenyl-9H-thioxanthine of Preparation Example 7 was used as a reactant to obtain 15 g of the target compound.

GC-Mass (theory: 377.12 g / mol, measurement: 377.51 g / mol)

[ Preparation Example  13] 13- methyl Diphenyl-12,13- Dihydro -5H- Indole [2,3-a] acridine  synthesis

The procedure of Preparation Example 1 was repeated except that 2-bromo-N- (4-bromophenyl) -N-phenylaniline and acetophenone were used as a reactant to obtain 16 g of the target compound.

GC-Mass (calculated: 436.19 g / mol, measured: 436.56 g / mol)

[ Preparation Example  14] 13- methyl Diphenyl-11,13- Dihydro -5H- Indol [2,3-b] acridine  synthesis

The procedure of Preparation Example 1 was repeated except that 2-bromo-N- (3-bromophenyl) -N-phenylalanine and acetophenone were used as a reactant, to thereby yield 14 g of the target compound.

GC-Mass (calculated: 436.19 g / mol, measured: 436.56 g / mol)

[ Preparation Example  15] 8- methyl -8, 13-diphenyl-8, 13- Dihydro -5H- Indole [2,3-c] acridine  Synthesis of

The procedure of Preparation Example 1 was repeated, except that 2-bromo-N- (2-bromophenyl) -N-phenylalanine and acetophenone were used as a reactant, to obtain 14 g of the title compound.

GC-Mass (calculated: 436.19 g / mol, measured: 436.56 g / mol)

[ Preparation Example  16] 7- methyl -7,12-diphenyl-12,13- Dihydro -7H- Indolo [3,2-c] acridine < / RTI >  synthesis

The procedure of Preparation Example 4 was repeated except that 4-bromo-9-methyl-9,10-diphenyl-9,10-dihydro-acridine of Preparation Example 15 was used as a reactant, ≪ / RTI >

GC-Mass (calculated: 436.19 g / mol, measured: 436.56 g / mol)

[ Preparation Example  17] 13- methyl -5,13-diphenyl-7,13- Dihydro -5H- Indolo [3,2-b] acridine  synthesis

The procedure of Preparation Example 4 was repeated except that 3-bromo-9-methyl-9,10-diphenyl-9,10-dihydro-acridine of Preparation Example 14 was used as a reactant, to obtain 8 g ≪ / RTI >

GC-Mass (calculated: 436.19 g / mol, measured: 436.56 g / mol)

[ Preparation Example  18] 13- methyl -5,13-diphenyl-8,13- Dihydro -5H- Indolo [3,2-a] acridine  synthesis

The procedure of Preparation Example 4 was repeated except that 2-bromo-9-methyl-9,10-diphenyl-9,10-dihydro-acridine of Preparation Example 13 was used as a reactant, ≪ / RTI >

 GC-Mass (calculated: 436.19 g / mol, measured: 436.56 g / mol)

[ Preparation Example  19] 13,13-diphenyl-12,13- Dihydrochromeno [3,2-a] carbazole  synthesis

The procedure of Preparation Example 1 was repeated, except that benzophenone was used as a reactant, to obtain 11 g of the target compound;

 GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  20] 13,13-diphenyl-11,13- Dihydrochromeno [3,2-b] carbazole  synthesis

The procedure of Preparation Example 2 was repeated except that benzophenone was used as a reactant, to obtain 9 g of the target compound;

GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  21] 8,8-diphenyl-5,8- Dihydrochromeno [3,2-c] carbazole  synthesis

The procedure of Preparation Example 3 was repeated except that benzophenone was used as the reactant, to thereby yield 14 g of the desired compound;

 GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  22] 7,7-diphenyl-7,13- Dihydrochromeno [2,3-a] carbazole  synthesis

The procedure of Preparation Example 4 was repeated, except that 4-bromo-9,9-diphenyl-9H-xanthene of Preparation Example 21 was used as a reactant, to thereby yield 9 g of the target compound.

 GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  23] 13,13-diphenyl-7,13- Dihydrochromeno [2,3-b] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 3-bromo-9,9-diphenyl-9H-xanthene of Preparation Example 20 was used as a reactant to obtain 9 g of the target compound.

GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  24] 13,13-diphenyl-8,13- Dihydrochromeno [2,3-c] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 2-bromo-9,9-diphenyl-9H-xanthene of Preparation Example 19 was used as a reactant to obtain 18 g of the target compound.

GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  25] 13,13-diphenyl-12,13- Dihydrothiochromeno [3,2-a] carbazole  synthesis

The procedure of Preparation Example 7 was repeated, except that benzophenone was used as a reactant, to obtain 10 g of the target compound;

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  26] 13,13-diphenyl-11,13- Dihydrothiochromeno [3,2-b] carbazole  synthesis

The procedure of Preparation Example 8 was repeated, except that benzophenone was used as a reactant, to obtain 12 g of the title compound;

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  27] 8,8-diphenyl-5,8- Dihydrothiochromeno [3,2-c] carbazole  synthesis

The procedure of Preparation Example 9 was repeated except that benzophenone was used as a reactant, to obtain 14 g of the target compound;

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  28] 7,7-phenyl-7,13- Dihydrothiochromeno [2,3-a] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 4-bromo-9,9-diphenyl-9H-thioxanthone of Preparation Example 27 was used as a reactant to obtain 17 g of the target compound.

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  29] 13,13-diphenyl-7,13- Dihydrothiochromeno [2,3-b] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 3-bromo-9,9-diphenyl-9H-thioxanthine of Preparation Example 26 was used as a reactant to obtain 14 g of the title compound.

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  30] 13,13-diphenyl-8,13- Dihydrochromeno [2,3-c] carbazole  synthesis

The procedure of Preparation Example 4 was repeated except that 2-bromo-9,9-diphenyl-9H-thioxanthone of Preparation Example 25 was used as a reactant to obtain 16 g of the target compound;

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  31] 5,13,13- Triphenyl -12,13- Dihydro -5H- Indolo [2,3-a] acridine < / RTI >  synthesis

The procedure of Preparation Example 13 was repeated, except that benzophenone was used as a reactant, to obtain 17 g of the target compound.

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  32] 5,13,13- Triphenyl -11,13- Dihydro -5H- Indolo [2,3-b] acridine < / RTI >  synthesis

The procedure of Preparation Example 14 was repeated, except that benzophenone was used as a reactant, to obtain 10 g of the desired compound;

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  33] 8,8,13- Triphenyl -8,13- Dihydro -5H- Indolo [2,3-c] acridine < / RTI >  synthesis

The procedure of Preparation Example 15 was repeated except that benzophenone was used as a reactant to obtain 16 g of the desired compound;

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  34] 7- methyl -7,12-diphenyl-12,13- Dihydro -7H- Indolo [3,2-c] acridine < / RTI >  synthesis

The procedure of Preparation Example 4 was repeated except that 4-bromo-9,9,10-triphenyl-9,10-dihydro-acridine of Preparation Example 33 was used as a reactant to obtain 13 g of the target compound .;

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  35] 5,13,13- Triphenyl -7,13- Dihydro -5H- Indolo [3,2-b] acridine  synthesis

The procedure of Preparation Example 4 was repeated except that 3-bromo-9,9,10-triphenyl-9,10-dihydro-acridine of Preparation Example 32 was used as a reactant to obtain 11 g of the title compound .;

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  36] 5,13,13- Triphenyl -8,13- Dihydro -5H- Indolo [3,2-a] acridine  synthesis

The procedure of Preparation Example 4 was repeated except that 2-bromo-9,9,10-triphenyl-9,10-dihydro-acridine of Preparation Example 31 was used as a reactant to obtain 12 g of the title compound .;

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  37] 11H- Spiro [chromeno [3,2-b] carbazole -13,9'- Fluorene ] Synthesis of

The procedure of Preparation Example 2 was repeated, except that 9H-fluoren-9-one was used as a reactant, to obtain 15 g of the desired compound;

GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  38] 5H- Spiro [chromeno [3,2-c] carbazole -8,9'- Fluorene ] Synthesis of

The procedure of Preparation Example 3 was repeated except that 9H-fluoren-9-one was used as the reactant, to obtain 14 g of the target compound;

 GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  39] 13H- Spiro [chromeno [2,3-a] carbazole -7,9'- Fluorene ] Synthesis of

The procedure of Preparation Example 4 was repeated except that 4'-bromospiro [fluorene-9,9'-xanthene of Preparation 38 was used as the reactant, to obtain 8 g of the target compound;

 GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  40] 7H- Spiro [chromeno [2,3-b] carbazole -13,9'- Fluorene ] Synthesis of

The procedure of Preparation Example 4 was repeated except that 3'-bromospiro [fluorene-9,9'-xanthene of Preparation Example 37 was used as a reactant, to obtain 8 g of the target compound;

GC-Mass (calculated: 423.16 g / mol, measured: 423.52 g / mol)

[ Preparation Example  41] 11'H - Spiro [fluorene-9,13'-thiochromene [3,2-b] Carbazole ] Synthesis of

The procedure of Preparation Example 8 was repeated except that 9H-fluoren-9-one was used as the reactant, to obtain 16 g of the target compound;

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  42] 5'H - Spiro [fluorene-9,8'-thio chromene [3,2-c] Carbazole ] Synthesis of

The procedure of Preparation Example 9 was repeated except that 9H-fluoren-9-one was used as a reactant, to obtain 14 g of the target compound;

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  43] 13'H - Spiro [fluorene-9,7'-thiochromene [2,3-a] Carbazole ] Synthesis of

The procedure of Preparation Example 4 was repeated except that 4'-bromospiro [fluorene-9,9'-thioxanthine] of Preparation Example 42 was used as a reaction product to obtain 14 g of the target compound;

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  44] 7'H - Spiro [fluorene-9,13'-thiochromene [2,3-b] Carbazole ] Synthesis of

The procedure of Preparation Example 4 was repeated except that 3'-bromospiro [fluorene-9,9'-thioxanthine] of Preparation Example 41 was used as a reactant to obtain 18 g of the target compound.

GC-Mass (calculated: 439.19 g / mol, measured: 439.58 g / mol)

[ Preparation Example  45] 5'-phenyl-5 ', 11'- Dihydroiso [fluorene-9,13'-indolo [2,3-b] acridine]

The procedure of Preparation Example 14 was repeated, except that 9H-fluoren-9-one was used as a reactant to obtain 12 g of the target compound;

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  46] 13'-phenyl-5 ', 13'- Dihydroiso [fluorene-9,8'-indolo [2,3-c] acridine]

The procedure of Preparation Example 15 was repeated, except that 9H-fluoren-9-one was used as a reactant, to obtain 10 g of the target compound;

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  47] 12'-phenyl-12 ', 13'- Dihydroiso [fluorene-9,7'-indolo [3,2-c] acridine]

The procedure of Preparation Example 4 was repeated except that 4-bromo-10-phenyl-10H-spiro [acridine-9,9'-fluorene] of Preparation Example 46 was used as a reactant, ≪ / RTI >

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Preparation Example  48] 5'-phenyl-5 ', 7'- Dihydroiso [fluorene-9,13'-indolo [3,2-b] acridine]

The procedure of Preparation Example 4 was repeated except that 3-bromo-10-phenyl-10H-spiro [acridine-9,9'-fluorene] of Preparation Example 45 was used as a reactant, ≪ / RTI >

GC-Mass (theory: 498.21 g / mol, measurement: 498.63 g / mol)

[ Synthetic example  1] Synthesis of Mat 1

250 mL of xylene was added to 10 g (27.6 mmol) of 13-methyl-13-phenyl-12,13-dihydrochromeno [3,2-a] carbazole obtained in Preparation Example 1 and 6.2 g (30.4 mmol) . 1.0 g (1.104 mmol) of Pd ₂ (dba) ₃ , 1.05 g (2.2 mmol) of Xphos and 6.6 g (69 mol) of NaOtBu were added and the mixture was refluxed at 120 ° C. for 24 hours. The reaction solution was cooled to room temperature and the reaction was terminated with 500 mL of an aqueous ammonium chloride solution. The mixture was extracted with 500 mL of MC and then washed with distilled water. The obtained organic layer was dried over anhydrous MgSO ₄ , distilled under reduced pressure and purified by silica gel column chromatography to obtain the desired compound (10.9 g, 91%).

¹ H-NMR:? 8.55 (d, 1H), 7.98 (dd, 2H), 7.58 (m, 4H), 7.35-7.15 (m, 10H), 7.01 HRMS [M] < ⁺ & gt ^; : 437.18

[ Synthetic example  2] Synthesis of Mat 2

The procedure of Synthesis Example 1 was repeated, except that 3-bromo-1,1'-biphenyl was used as a reactant, to thereby yield the desired compound (10.2 g).

HRMS [M] < + >: 513.21

[ Synthetic example  3] Synthesis of Mat 3

The procedure of Synthesis Example 1 was repeated except that 3-bromo-9,9-dimethyl-9H-fluorene was used as a reactant, to thereby yield 6 g of the target compound.

HRMS [M] < + >: 553.24

[ Synthetic example  4] Synthesis of Mat 4

The procedure of Synthesis Example 1 was repeated except that 4- (4-chlorophenyl) isoquinoline was used as a reactant, to obtain 5 g of the desired compound.

HRMS [M] < + >: 564.22

[ Synthetic example  5] Synthesis of Mat 5

The same procedure as in [Synthesis Example 1] was repeated, except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline was used as a reactant.

HRMS [M] < + >: 691.26

[ Synthetic example  6] Synthesis of Mat 6

The procedure of Synthesis Example 1 was repeated except for using 2- (4-bromophenyl) -1-phenyl-1H-benzo [d] imidazole as a reactant to obtain 8 g of the target compound.

HRMS [M] < + >: 629.25

[ Synthetic example  7] Synthesis of Mat 7

The procedure of Synthesis Example 1 was repeated, except that 9- (3-bromophenyl) -9H-carbazole was used as a reactant to obtain 9 g of the desired compound.

HRMS [M] < + >: 602.24

[ Synthetic example  8] Synthesis of Mat 8

The procedure of Synthesis Example 1 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used as a reactant, to obtain 8 g of the target compound.

HRMS [M] < + >: 592.23

[ Synthetic example  9] Synthesis of Mat 9

The procedure of Synthesis Example 1 was repeated, except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used as a reactant, to obtain 10 g of the target compound.

HRMS [M] < + >: 668.26

[ Synthetic example  10] Synthesis of Mat 10

Except that 2- (4'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine was used as a reaction product. 1, 9 g of the desired compound was obtained.

HRMS [M] < + >: 744.29

[ Synthetic example  11] Synthesis of Mat 11

Except that N - ([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl) -9,9-dimethyl-9H- fluoren- The procedure of Synthesis Example 1 was repeated to obtain 7 g of the target compound.

HRMS [M] < + >: 796.35

[ Synthetic example  12] Synthesis of Mat 12

The procedure of Synthesis Example 1 was repeated except that 2- (4-bromophenyl) triphenylene was used as a reactant, to obtain 6 g of the desired compound.

HRMS [M] < + >: 663.26

[ Synthetic example  13] Synthesis of Mat 13

The procedure of Synthesis Example 1 was repeated except for using 4- (4-bromophenyl) dibenzo [b, d] thiophene as a reactant, to thereby yield 8 g of the desired compound.

HRMS [M] < + >: 619.20

[ Synthetic example  14] Synthesis of Mat 14

The same procedure as in Synthesis Example 1 was carried out except that 3-bromo-9- (4,6-diphenyl-1,3,5-triazin-2-yl) -9H-carbazole was used as a reaction product 9 g of the desired compound was obtained.

HRMS [M] < + >: 757.28

[ Synthetic example  15] Synthesis of Mat 15

The procedure of Synthesis Example 2 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] 8 g.

HRMS [M] < + >: 513.21

[ Synthetic example  16] Synthesis of Mat 16

The procedure of Synthesis Example 3 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 2 was used as a reactant, 6 g.

HRMS [M] < + >: 553.24

[ Synthetic example  17] Synthesis of Mat 17

The procedure of Synthesis Example 5 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 2 was used as a reactant, 5 g.

HRMS [M] < + >: 691.26

[ Synthetic example  18] Synthesis of Mat 18

The procedure of Synthesis Example 7 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 2 was used as a reactant, 7 g.

HRMS [M] < + >: 602.24

[ Synthetic example  19] Synthesis of Mat 19

The procedure of Synthesis Example 8 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 2 was used as a reactant, 8 g.

HRMS [M] < + >: 592.23

[ Synthetic example  20] Synthesis of Mat 20

The procedure of Synthesis Example 9 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 2 was used as a reactant, 6 g.

HRMS [M] < + >: 668.26

[ Synthetic example  21] Synthesis of Mat 21

The procedure of Synthesis Example 10 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 2 was used as a reactant, 5 g.

HRMS [M] < + >: 744.29

[ Synthetic example  22] Synthesis of Mat 22

The procedure of Synthesis Example 11 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 2 was used as a reactant, 5 g.

HRMS [M] < + >: 796.35

[ Synthetic example  23] Synthesis of Mat 23

The procedure of Synthesis Example 14 was repeated except that 13-methyl-13-phenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 2 was used as a reactant, 9 g; HRMS [M] < + >: 757.28

[ Synthetic example  24] Synthesis of Mat 24

The procedure of Synthesis Example 2 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] 10 g.

HRMS [M] < + >: 513.21

[ Synthetic example  25] Synthesis of Mat 25

The procedure of Synthesis Example 3 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 3 was used as a reactant, 7 g.

HRMS [M] < + >: 553.24

[ Synthetic example  26] Synthesis of Mat 26

The procedure of Synthesis Example 5 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] 7 g.

HRMS [M] < + >: 691.26

[ Synthetic example  27] Synthesis of Mat 27

The procedure of Synthesis Example 7 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 3 was used as a reactant, 8 g.

HRMS [M] < + >: 602.24

[ Synthetic example  28] Synthesis of Mat 28

Except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 3 was used as a reactant, the objective compound 6 g.

HRMS [M] < + >: 592.23

[ Synthetic example  29] Synthesis of Mat 29

The procedure of Synthesis Example 9 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 3 was used as a reactant, 5 g.

HRMS [M] < + >: 668.26

[ Synthetic example  30] Synthesis of Mat 30

The procedure of Synthesis Example 10 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] 7 g.

HRMS [M] < + >: 744.29

[ Synthetic example  31] Synthesis of Mat 31

The procedure of Synthesis Example 11 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 3 was used as a reactant, 8 g.

HRMS [M] < + >: 796.35

[ Synthetic example  32] Synthesis of Mat 32

The procedure of Synthesis Example 14 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 3 was used as a reactant, 10 g.

HRMS [M] < + >: 757.28

[ Synthetic example  33] Synthesis of Mat 33

The procedure of Synthesis Example 2 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 8 g.

HRMS [M] < + >: 513.21

[ Synthetic example  34] Synthesis of Mat 34

The procedure of Synthesis Example 3 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 4 g.

HRMS [M] < + >: 553.24

[ Synthetic example  35] Synthesis of Mat 35

The procedure of Synthesis Example 5 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 5 g.

HRMS [M] < + >: 691.26

[ Synthetic example  36] Synthesis of Mat 36

The procedure of Synthesis Example 7 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 9g.

HRMS [M] < + >: 602.24

[ Synthetic example  37] Synthesis of Mat 37

The procedure of Synthesis Example 8 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 3 g.

HRMS [M] < + >: 592.23

[ Synthetic example  38] Synthesis of Mat 38

The procedure of Synthesis Example 9 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 8 g.

HRMS [M] < + >: 668.26

[ Synthetic example  39] Synthesis of Mat 39

The procedure of Synthesis Example 10 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 7 g.

HRMS [M] < + >: 744.29

[ Synthetic example  40]] Synthesis of Mat 40

The procedure of Synthesis Example 11 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 5 g.

HRMS [M] < + >: 796.35

[ Synthetic example  41] Synthesis of Mat 41

The procedure of Synthesis Example 14 was repeated except that 7-methyl-7-phenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 4 was used as a reactant, 9g.

HRMS [M] < + >: 757.28

[ Synthetic example  42] Synthesis of Mat 42

The procedure of Synthesis Example 2 was repeated except for using 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] 10 g.

HRMS [M] < + >: 513.21

[ Synthetic example  43] Synthesis of Mat 43

The procedure of Synthesis Example 3 was repeated except that 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] 6 g.

HRMS [M] < + >: 553.24

[ Synthetic example  44] Mat 44 Synthesis

The procedure of Synthesis Example 5 was repeated except that 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] 5 g.

HRMS [M] < + >: 691.26

[ Synthetic example  45] Synthesis of Mat 45

The procedure of Synthesis Example 7 was repeated except that 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] 6 g.

HRMS [M] < + >: 602.24

[ Synthetic example  46] Synthesis of Mat 46

The procedure of Synthesis Example 8 was repeated except that 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] carbazole obtained in Preparation Example 5 was used as a reactant, 4 g.

HRMS [M] < + >: 592.23

[ Synthetic example  47] Synthesis of Mat 47

The procedure of Synthesis Example 9 was repeated except that 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] carbazole obtained in Preparation Example 5 was used as a reactant, 4 g.

HRMS [M] < + >: 668.26

[ Synthetic example  48] Synthesis of Mat 48

The procedure of Synthesis Example 10 was repeated except that 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] carbazole obtained in Preparation Example 5 was used as a reactant, 6 g.

HRMS [M] < + >: 744.29

[ Synthetic example  49]] Synthesis of Mat 49

The procedure of Synthesis Example 11 was repeated except that 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] carbazole obtained in Preparation Example 5 was used as a reactant, 10 g.

HRMS [M] < + >: 796.35

[ Synthetic example  50] Synthesis of Mat 50

The procedure of Synthesis Example 14 was repeated except that 13-methyl-13-phenyl-7,13-dihydrochromeno [2,3-b] carbazole obtained in Preparation Example 5 was used as a reactant, 7 g.

HRMS [M] < + >: 757.28

[ Synthetic example  51] Synthesis of Mat 51

The procedure of Synthesis Example 2 was repeated except for using 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] 7 g.

HRMS [M] < + >: 513.21

[ Synthetic example  52] Synthesis of Mat 52

The procedure of Synthesis Example 3 was repeated except that 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 6 was used as a reactant, 8 g.

HRMS [M] < + >: 553.24

[ Synthetic example  53] Mat 53 Composite

The procedure of Synthesis Example 5 was repeated except that 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] 6 g.

HRMS [M] < + >: 691.26

[ Synthetic example  54] Synthesis of Mat 54

The procedure of Synthesis Example 7 was repeated except that 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 6 was used as a reactant, 5 g.

HRMS [M] < + >: 602.24

[ Synthetic example  55] Synthesis of Mat 55

The procedure of Synthesis Example 8 was repeated except that 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 6 was used as a reactant, 4 g.

HRMS [M] < + >: 592.23

[ Synthetic example  56] Synthesis of Mat 56

The procedure of Synthesis Example 9 was repeated except that 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 6 was used as a reactant, 6 g.

HRMS [M] < + >: 668.26

[ Synthetic example  57] Synthesis of Mat 57

The procedure of Synthesis Example 10 was repeated except that 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 6 was used as a reactant, 10 g.

HRMS [M] < + >: 744.29

[ Synthetic example  58] Synthesis of Mat 58

The procedure of Synthesis Example 11 was repeated except that 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 6 was used as a reactant, 7 g.

HRMS [M] < + >: 796.35

[ Synthetic example  59] Synthesis of Mat 59

The procedure of Synthesis Example 14 was repeated except that 13-methyl-13-phenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 6 was used as a reactant, 9g.

HRMS [M] < + >: 757.28

[ Synthetic example  60] Synthesis of Mat 60

The same procedure as in [Synthesis Example 3] was carried out except that 13-methyl-13-phenyl-12,13-dihydrothiochromeno [3,2-a] 6 g of the aimed compound was obtained; HRMS [M] < + >: 569.22

[ Synthetic example  61] Synthesis of Mat 61

The procedure of Synthesis Example 5 was repeated except that 13-methyl-13-phenyl-12,13-dihydrothiochromeno [3,2-a] 5 g of a compound was obtained.

HRMS [M] < + >: 707.24

[ Synthetic example  62] Synthesis of Mat 62

The procedure of Synthesis Example 7 was repeated except that 13-methyl-13-phenyl-12,13-dihydrothiochromeno [3,2-a] 10 g of a compound was obtained.

HRMS [M] < + >: 618.21

[ Synthetic example  63] Synthesis of Mat 63

The procedure of Synthesis Example 8 was repeated except that 13-methyl-13-phenyl-12,13-dihydrothiochromeno [3,2-a] carbazole obtained in Preparation Example 7 was used as a reactant, 8 g of a compound was obtained.

HRMS [M] < + >: 608.20

[ Synthetic example  64] Synthesis of Mat 64

The procedure of Synthesis Example 9 was repeated except that 13-methyl-13-phenyl-12,13-dihydrothiochromeno [3,2-a] 11 g of a compound was obtained.

HRMS [M] < + >: 684.23

[ Synthetic example  65] Synthesis of Mat 65

The procedure of Synthesis Example 10 was repeated except that 13-methyl-13-phenyl-12,13-dihydrothiochromeno [3,2-a] carbazole obtained in Preparation Example 7 was used as a reactant, 9 g of a compound was obtained.

HRMS [M] < + >: 760.27

[ Synthetic example  66] Synthesis of Mat 66

The procedure of Synthesis Example 11 was repeated except that 13-methyl-13-phenyl-12,13-dihydrothiochromeno [3,2-a] carbazole obtained in Preparation Example 7 was used as a reactant, 7 g of a compound was obtained.

HRMS [M] < + >: 812.32

[ Synthetic example  67] Synthesis of Mat 67

The procedure of Synthesis Example 3 was repeated except that 13-methyl-13-phenyl-11,13-dihydrothiochromeno [3,2-b] 6 g of a compound was obtained.

HRMS [M] < + >: 569.22

[ Synthetic example  68] Synthesis of Mat 68

The procedure of Synthesis Example 5 was repeated except that 13-methyl-13-phenyl-11,13-dihydrothiochromeno [3,2-b] 4 g of a compound was obtained.

HRMS [M] < + >: 707.24

[ Synthetic example  69] Synthesis of Mat 69

The procedure of Synthesis Example 7 was repeated except that 13-methyl-13-phenyl-11,13-dihydrothiochromeno [3,2-b] 7 g of a compound was obtained.

HRMS [M] < + >: 618.21

[ Synthetic example  70] Mat70  synthesis

The procedure of Synthesis Example 8 was repeated except that 13-methyl-13-phenyl-11,13-dihydrothiochromeno [3,2-b] carbazole obtained in Preparation Example 8 was used as a reactant, 10 g of a compound was obtained.

HRMS [M] < + >: 608.20

[ Synthetic example  71] Synthesis of Mat 71

The procedure of Synthesis Example 9 was repeated except that 13-methyl-13-phenyl-11,13-dihydrothiochromeno [3,2-b] carbazole obtained in Preparation Example 8 was used as a reactant, 5 g of a compound was obtained.

HRMS [M] < + >: 684.23

[ Synthetic example  72] Synthesis of Mat 72

The procedure of Synthesis Example 10 was repeated except that 13-methyl-13-phenyl-11,13-dihydrothiochromeno [3,2-b] carbazole obtained in Preparation Example 8 was used as a reactant, 5 g of a compound was obtained.

HRMS [M] < + >: 760.27

[ Synthetic example  73] Synthesis of Mat 73

The procedure of Synthesis Example 11 was repeated except that 13-methyl-13-phenyl-11,13-dihydrothiochromeno [3,2-b] 6 g of a compound was obtained.

HRMS [M] < + >: 812.32

[ Synthetic example  74] Synthesis of Mat 74

The procedure of Synthesis Example 3 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 9 was used as a reactant, 12 g.

HRMS [M] < + >: 569.22

[ Synthetic example  75] Synthesis of Mat 75

The procedure of Synthesis Example 5 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 9 was used as a reactant, 10 g.

HRMS [M] < + >: 707.24

[ Synthetic example  76] Synthesis of Mat 76

The procedure of Synthesis Example 7 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 9 was used as a reactant, 8 g.

HRMS [M] < + >: 618.21

[ Synthetic example  77] Mat77  synthesis

The procedure of Synthesis Example 8 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 9 was used as a reactant, 7 g.

HRMS [M] < + >: 608.20

[ Synthetic example  78] Synthesis of Mat 78

The procedure of Synthesis Example 9 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 9 was used as a reactant, 6 g.

HRMS [M] < + >: 684.23

[ Synthetic example  79] Synthesis of Mat 79

The procedure of Synthesis Example 10 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 9 was used as a reactant, 5.5 g.

HRMS [M] < + >: 760.27

[ Synthetic example  80] Synthesis of Mat 80

The procedure of Synthesis Example 11 was repeated except that 8-methyl-8-phenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 9 was used as a reactant, 4 g.

HRMS [M] < + >: 812.32

[ Synthetic example  81] Synthesis of Mat 81

The procedure of Synthesis Example 3 was repeated except that 7-methyl-7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 10 was used as a reactant, 9 g of a compound was obtained.

HRMS [M] < + >: 569.22

[ Synthetic example  82] Synthesis of Mat 82

The procedure of Synthesis Example 5 was repeated except that 7-methyl-7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 10 was used as a reactant, 9 g of a compound was obtained.

HRMS [M] < + >: 707.24

[ Synthetic example  83] Synthesis of Mat 83

The procedure of Synthesis Example 7 was repeated except that 7-methyl-7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 10 was used as a reactant, 8 g of a compound was obtained.

HRMS [M] < + >: 618.21

[ Synthetic example  84] Mat84  synthesis

The procedure of Synthesis Example 8 was repeated except that 7-methyl-7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 10 was used as a reactant, 9 g of a compound was obtained.

HRMS [M] < + >: 608.20

[ Synthetic example  85] Synthesis of Mat 85

The procedure of Synthesis Example 9 was repeated except that 7-methyl-7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 10 was used as a reactant, 6 g of a compound was obtained.

HRMS [M] < + >: 684.23

[ Synthetic example  86] Synthesis of Mat 86

The procedure of Synthesis Example 10 was repeated except that 7-methyl-7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 10 was used as a reactant, 4 g of a compound was obtained.

HRMS [M] < + >: 760.27

[ Synthetic example  87] Synthesis of Mat 87

The procedure of Synthesis Example 11 was repeated except that 7-methyl-7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 10 was used as a reactant, 4 g of a compound was obtained.

HRMS [M] < + >: 812.32

[ Synthetic example  88] Synthesis of Mat 88

The procedure of Synthesis Example 3 was repeated except that 13-methyl-13-phenyl-7,13-dihydrothiochromeno [2,3-b] carbazole obtained in Preparation Example 11 was used as a reactant, 6 g of a compound was obtained.

HRMS [M] < + >: 569.22

[ Synthetic example  89] Synthesis of Mat 89

The procedure of Synthesis Example 5 was repeated except that 13-methyl-13-phenyl-7,13-dihydrothiochromeno [2,3-b] 8 g of a compound was obtained.

HRMS [M] < + >: 707.24

[ Synthetic example  90] Synthesis of Mat 90

The procedure of Synthesis Example 7 was repeated except that 13-methyl-13-phenyl-7,13-dihydrothiochromeno [2,3-b] 10 g of a compound was obtained.

HRMS [M] < + >: 618.21

[ Synthetic example  91] Synthesis of Mat 91

The procedure of Synthesis Example 8 was repeated except that 13-methyl-13-phenyl-7,13-dihydrothiochromeno [2,3-b] carbazole obtained in Preparation Example 11 was used as a reactant, 7 g of a compound was obtained.

HRMS [M] < + >: 608.20

[ Synthetic example  92] Synthesis of Mat 92

The procedure of Synthesis Example 9 was repeated except that 13-methyl-13-phenyl-7,13-dihydrothiochromeno [2,3-b] 12 g of a compound was obtained.

HRMS [M] < + >: 684.23

[ Synthetic example  93] Synthesis of Mat 93

The procedure of Synthesis Example 10 was repeated except that 13-methyl-13-phenyl-7,13-dihydrothiochromeno [2,3-b] carbazole obtained in Preparation Example 11 was used as a reactant, 7 g of a compound was obtained.

HRMS [M] < + >: 760.27

[ Synthetic example  94] Synthesis of Mat 94

The procedure of Synthesis Example 11 was repeated except that 13-methyl-13-phenyl-7,13-dihydrothiochromeno [2,3-b] carbazole obtained in Preparation Example 11 was used as a reactant, 6 g of a compound was obtained.

HRMS [M] < + >: 812.32

[ Synthetic example  95] Synthesis of Mat 95

The procedure of Synthesis Example 3 was repeated except that 13-methyl-13-phenyl-8,13-dihydrothiochromeno [2,3-c] 4 g of a compound was obtained.

HRMS [M] < + >: 569.22

[ Synthetic example  96] Synthesis of Mat 96

The procedure of Synthesis Example 5 was repeated except that 13-methyl-13-phenyl-8,13-dihydrothiochromeno [2,3-c] 5 g of a compound was obtained.

HRMS [M] < + >: 707.24

[ Synthetic example  97] Synthesis of Mat 97

The procedure of Synthesis Example 7 was repeated except that 13-methyl-13-phenyl-8,13-dihydrothiochromeno [2,3-c] carbazole obtained in Preparation Example 12 was used as a reactant, 6 g of a compound was obtained.

HRMS [M] < + >: 618.21

[ Synthetic example  98] Synthesis of Mat 98

The procedure of Synthesis Example 8 was repeated except that 13-methyl-13-phenyl-8,13-dihydrothiochromeno [2,3-c] 3 g of a compound was obtained.

HRMS [M] < + >: 608.20

[ Synthetic example  99] Synthesis of Mat 99

The procedure of Synthesis Example 9 was repeated except that 13-methyl-13-phenyl-8,13-dihydrothiochromeno [2,3-c] carbazole obtained in Preparation Example 12 was used as a reactant, 6 g of a compound was obtained.

HRMS [M] < + >: 684.23

[ Synthetic example  100] Synthesis of Mat 100

The procedure of Synthesis Example 10 was repeated except that 13-methyl-13-phenyl-8,13-dihydrothiochromeno [2,3-c] 9 g of a compound was obtained.

HRMS [M] < + >: 760.27

[ Synthetic example  101] Synthesis of Mat 101

The procedure of Synthesis Example 11 was repeated except that 13-methyl-13-phenyl-8,13-dihydrothiochromeno [2,3-c] carbazole obtained in Preparation Example 12 was used as a reactant, 9 g of a compound was obtained.

HRMS [M] < + >: 812.32

[ Synthetic example  102] Synthesis of Mat 102

The same procedure as in Synthesis Example 3 was carried out except that 13-methyl-5,13-diphenyl-12,13-dihydro-5H-indole [2,3-a] 6 g of the target compound was obtained.

HRMS [M] < + >: 628.29

[ Synthetic example  103] Synthesis of Mat 103

The same procedure as in Synthesis Example 5 was carried out except that 13-methyl-5,13-diphenyl-12,13-dihydro-5H-indole [2,3-a] To obtain 5 g of the aimed compound.

HRMS [M] < + >: 766.31

[ Synthetic example  104] Synthesis of Mat 104

The same procedure as in Synthesis Example 7 was carried out except that 13-methyl-5,13-diphenyl-12,13-dihydro-5H-indole [2,3-a] To obtain 5 g of the aimed compound.

HRMS [M] < + >: 677.28

[ Synthetic example  105] Synthesis of Mat 105

The same procedure as in Synthesis Example 8 was carried out except that 13-methyl-5,13-diphenyl-12,13-dihydro-5H-indole [2,3-a] To obtain 4 g of the target compound.

HRMS [M] < + >: 667.27

[ Synthetic example  106] Synthesis of Mat 106

The same procedure as in Synthesis Example 9 was carried out except that 13-methyl-5,13-diphenyl-12,13-dihydro-5H-indole [2,3-a] To obtain 7 g of the target compound.

HRMS [M] < + >: 743.30

[ Synthetic example  107] Synthesis of Mat 107

The same procedure as in Synthesis Example 10 was carried out except that 13-methyl-5,13-diphenyl-12,13-dihydro-5H-indole [2,3-a] To obtain 7 g of the target compound.

HRMS [M] < + >: 819.34

[ Synthetic example  108] Synthesis of Mat 108

The same procedure as in Synthesis Example 11 was carried out except that 13-methyl-5,13-diphenyl-12,13-dihydro-5H-indole [2,3-a] To obtain 9 g of the aimed compound.

HRMS [M] < + >: 871.39

[ Synthetic example  109] Synthesis of Mat 109

The same procedure as in Synthesis Example 3 was carried out except that 13-methyl-5,13-diphenyl-11,13-dihydro-5H-indole [2,3-b] 4 g of the target compound was obtained.

HRMS [M] < + >: 628.29

[ Synthetic example  110] Synthesis of Mat 110

The procedure of Synthesis Example 5 was repeated except that 13-methyl-5,13-diphenyl-11,13-dihydro-5H-indole [2,3- b] 5 g of the target compound was obtained.

HRMS [M] < + >: 766.31

[ Synthetic example  111] Synthesis of Mat 111

The procedure of Synthesis Example 7 was repeated except that 13-methyl-5,13-diphenyl-11,13-dihydro-5H-indole [2,3- b] 4 g of the target compound was obtained.

HRMS [M] < + >: 677.28

[ Synthetic example  112] Synthesis of Mat 112

The same procedure as in Synthesis Example 8 was carried out except that 13-methyl-5,13-diphenyl-11,13-dihydro-5H-indole [2,3-b] 6 g of the target compound was obtained.

HRMS [M] < + >: 667.27

[ Synthetic example  113] Synthesis of Mat 113

The same procedure as in Synthesis Example 9 was carried out except that 13-methyl-5,13-diphenyl-11,13-dihydro-5H-indole [2,3-b] 9 g of the aimed compound was obtained.

HRMS [M] < + >: 743.30

[ Synthetic example  114] Synthesis of Mat 114

The procedure of Synthesis Example 10 was repeated except that 13-methyl-5,13-diphenyl-11,13-dihydro-5H-indole [2,3- b] To obtain 8 g of the target compound.

HRMS [M] < + >: 819.34

[ Synthetic example  115] Synthesis of Mat 115

The same procedure as in Synthesis Example 11 was carried out except that 13-methyl-5,13-diphenyl-11,13-dihydro-5H-indole [2,3-b] 6 g of the target compound was obtained.

HRMS [M] < + >: 871.39

[ Synthetic example  116] Synthesis of Mat 116

Synthesis Example 3] was repeated except that 8-methyl-8,13-diphenyl-8,13-dihydro-5H-indole [2,3-c] The same procedure was followed to obtain 10 g of the title compound;

HRMS [M] < + >: 628.29

[ Synthetic example  117] Synthesis of Mat 117

The procedure of Synthesis Example 5 was repeated except that 8-methyl-8,13-diphenyl-8,13-dihydro-5H-indole [2,3- c] To obtain 11 g of the target compound.

HRMS [M] < + >: 766.31

[ Synthetic example  118] Synthesis of Mat 118

The procedure of Synthesis Example 7 was repeated except for using 8-methyl-8,13-diphenyl-8,13-dihydro-5H-indole [2,3-c] 5 g of the target compound was obtained.

HRMS [M] < + >: 677.28

[ Synthetic example  119] Synthesis of Mat 119

The procedure of Synthesis Example 8 was repeated except that 8-methyl-8,13-diphenyl-8,13-dihydro-5H-indole [2,3-c] 6 g of the target compound was obtained.

HRMS [M] < + >: 667.27

[ Synthetic example  120] Synthesis of Mat 120

The procedure of Synthesis Example 9 was repeated except for using 8-methyl-8,13-diphenyl-8,13-dihydro-5H-indole [2,3- c] To obtain 7 g of the aimed compound.

HRMS [M] < + >: 743.30

[ Synthetic example  121] Synthesis of Mat 121

The procedure of Synthesis Example 10 was repeated except that 8-methyl-8,13-diphenyl-8,13-dihydro-5H-indole [2,3-c] To obtain 8 g of the target compound.

HRMS [M] < + >: 819.34

[ Synthetic example  122] Synthesis of Mat 112

The same procedure as in Synthesis Example 11 was carried out except that 8-methyl-8,13-diphenyl-8,13-dihydro-5H-indole [2,3-c] To obtain 12 g of the target compound.

HRMS [M] < + >: 871.39

[ Synthetic example  123] Synthesis of Mat 123

The same procedure as in Synthesis Example 3 was repeated except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] The same procedure was followed to obtain 9 g of the title compound; HRMS [M] < + >: 628.29

[ Synthetic example  124] Synthesis of Mat 124

Except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] acridine obtained in Preparation Example 16 was used as a reactant in Synthesis Example 5 The same procedure was followed to obtain 5 g of the target compound.

HRMS [M] < + >: 766.31

[ Synthetic example  125] Synthesis of Mat 125

The same procedure as in Synthesis Example 7 was repeated except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] The same procedure was followed to obtain 6 g of the target compound.

HRMS [M] < + >: 677.28

[ Synthetic example  126] Synthesis of Mat 126

The reaction was carried out in the same manner as in Synthesis Example 8 except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] The same procedure was followed to obtain 8 g of the target compound.

HRMS [M] < + >: 667.27

[ Synthetic example  127] Synthesis of Mat 127

The reaction was carried out in the same manner as in Synthesis Example 9, except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] The same procedure was followed to obtain 9 g of the target compound.

HRMS [M] < + >: 743.30

[ Synthetic example  128] Synthesis of Mat 128

The same procedure as in Synthesis Example 10 was repeated except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] The same procedure was followed to obtain 5 g of the target compound.

HRMS [M] < + >: 819.34

[ Synthetic example  129] Synthesis of Mat 129

The reaction was carried out in the same manner as in Synthesis Example 11, except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] The same procedure was followed to obtain 4 g of the target compound.

HRMS [M] < + >: 871.39

[ Synthetic example  130] Synthesis of Mat 130

Except that 13-methyl-5,13-diphenyl-7,13-dihydro-5H-indolo [3,2-b] acridine obtained in Preparation Example 17 was used as a reactant. The same procedure was followed to obtain 8 g of the target compound.

HRMS [M] < + >: 628.29

[ Synthetic example  131] Synthesis of Mat 131

Except that 13-methyl-5,13-diphenyl-7,13-dihydro-5H-indolo [3,2-b] acridine obtained in Preparation Example 17 was used as a reactant. The same procedure was followed to obtain 7 g of the target compound.

HRMS [M] < + >: 766.31

[ Synthetic example  132] Synthesis of Mat 132

Except that 13-methyl-5,13-diphenyl-7,13-dihydro-5H-indolo [3,2- b] acridine obtained in Preparation Example 17 was used as a reactant. The same procedure was followed to obtain 9 g of the target compound.

HRMS [M] < + >: 677.28

[ Synthetic example  133] Synthesis of Mat 133

Except that 13-methyl-5,13-diphenyl-7,13-dihydro-5H-indolo [3,2-b] acridine obtained in Preparation Example 17 was used as a reactant. The same procedure was followed to obtain 8 g of the target compound.

HRMS [M] < + >: 667.27

[ Synthetic example  134] Synthesis of Mat 134

Except that 13-methyl-5,13-diphenyl-7,13-dihydro-5H-indolo [3,2- b] acridine obtained in Preparation Example 17 was used as a reactant. The same procedure was followed to obtain 6 g of the target compound.

HRMS [M] < + >: 743.30

[ Synthetic example  135] Synthesis of Mat 135

Except that 13-methyl-5,13-diphenyl-7,13-dihydro-5H-indolo [3,2- b] acridine obtained in Preparation Example 17 was used as a reactant. The same procedure was followed to obtain 5 g of the target compound.

HRMS [M] < + >: 819.34

[ Synthetic example  136] Synthesis of Mat 136

In the same manner as in Synthesis Example 11, except that 13-methyl-5,13-diphenyl-7,13-dihydro-5H-indolo [3,2- b] The same procedure was followed to obtain 4.58 g of the title compound.

HRMS [M] < + >: 871.39

[ Synthetic example  137] Synthesis of Mat 137

Except that 13-methyl-5,13-diphenyl-8,13-dihydro-5H-indolo [3,2-a] acridine obtained in Preparation Example 18 was used as a reactant. The same procedure was followed to obtain 6.2 g of the target compound.

HRMS [M] < + >: 628.29

[ Synthetic example  138] Synthesis of Mat 138

Except that 13-methyl-5,13-diphenyl-8,13-dihydro-5H-indolo [3,2-a] acridine obtained in Preparation Example 18 was used as a reactant. The same procedure was followed to obtain 5 g of the target compound.

HRMS [M] < + >: 766.31

[ Synthetic example  139] Synthesis of Mat 139

Except that 13-methyl-5,13-diphenyl-8,13-dihydro-5H-indolo [3,2-a] acridine obtained in Preparation Example 18 was used as a reactant. The same procedure was followed to obtain 5.3 g of the target compound.

HRMS [M] < + >: 677.28

[ Synthetic example  140] Synthesis of Mat 140

Except that 13-methyl-5,13-diphenyl-8,13-dihydro-5H-indolo [3,2-a] acridine obtained in Preparation Example 18 was used as a reactant. The same procedure was followed to obtain 8 g of the target compound.

HRMS [M] < + >: 667.27

[ Synthetic example  141] Synthesis of Mat 141

Except that 13-methyl-5,13-diphenyl-8,13-dihydro-5H-indolo [3,2-a] acridine obtained in Preparation Example 18 was used as a reactant. The same procedure was followed to obtain 6.7 g of the desired compound.

HRMS [M] < + >: 743.30

[ Synthetic example  142] Synthesis of Mat 142

Except that 13-methyl-5,13-diphenyl-8,13-dihydro-5H-indolo [3,2-a] acridine obtained in Preparation Example 18 was used as a reactant. The same procedure was followed to obtain the desired compound (5.5 g).

HRMS [M] < + >: 819.34

[ Synthetic example  143] Synthesis of Mat 143

In the same manner as in Synthesis Example 11 except that 13-methyl-5,13-diphenyl-8,13-dihydro-5H-indolo [3,2-a] The same procedure was followed to obtain 4.8 g of the title compound.

HRMS [M] < + >: 871.39

[ Synthetic example  144] Synthesis of Mat 144

The procedure of Synthesis Example 3 was repeated except that 13,13-diphenyl-12,13-dihydrochromeno [3,2-a] carbazole obtained in Preparation Example 19 was used as a reactant, g.

HRMS [M] < + >: 615.26

[ Synthetic example  145] Synthesis of Mat 145

The procedure of Synthetic Example 8 was repeated except that 13,13-diphenyl-12,13-dihydrochromeno [3,2-a] carbazole obtained in Preparation Example 19 was used as a reactant, to obtain the desired compound 4.9 g.

HRMS [M] < + >: 654.24

[ Synthetic example  146] Synthesis of Mat 146

The same procedure as in Synthesis Example 9 was carried out except that 13,13-diphenyl-12,13-dihydrochromeno [3,2-a] carbazole obtained in Preparation Example 19 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 730.27

[ Synthetic example  147] Synthesis of Mat 147

The procedure of Synthesis Example 3 was repeated except that 13,13-diphenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 20 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 615.26

[ Synthetic example  148] Synthesis of Mat 148

The procedure of Synthetic Example 8 was repeated except that 13,13-diphenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 20 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 654.24

[ Synthetic example  149] Synthesis of Mat 149

The same procedure as in Synthesis Example 9 was carried out except that 13,13-diphenyl-11,13-dihydrochromeno [3,2-b] carbazole obtained in Preparation Example 20 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 730.27

[ Synthetic example  150] Synthesis of Mat 150

The procedure of Synthesis Example 3 was repeated except that 8,8-diphenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 21 was used as a reaction product, ≪ / RTI >

HRMS [M] < + >: 615.26

[ Synthetic example  151] Synthesis of Mat 151

The procedure of Synthetic Example 8 was repeated except that 8,8-diphenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 21 was used as a reactant to obtain the desired compound 6.2 g.

HRMS [M] < + >: 654.24

[ Synthetic example  152] Synthesis of Mat 152

The procedure of Synthesis Example 9 was repeated except that 8,8-diphenyl-5,8-dihydrochromeno [3,2-c] carbazole obtained in Preparation Example 21 was used as a reactant, g.

HRMS [M] < + >: 730.27

[ Synthetic example  153] Synthesis of Mat 153

The procedure of Synthesis Example 3 was repeated except that 7,7-diphenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 22 was used as a reactant, to obtain the desired compound 6.9 g.

HRMS [M] < + >: 615.26

[ Synthetic example  154] Synthesis of Mat 154

The same procedure as in Synthesis Example 8 was carried out except that 7,7-diphenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 22 was used as a reactant, to obtain 8 g ≪ / RTI >

HRMS [M] < + >: 654.24

[ Synthetic example  155] Synthesis of Mat 155

The procedure of Synthesis Example 9 was repeated except that the 7,7-diphenyl-7,13-dihydrochromeno [2,3-a] carbazole obtained in Preparation Example 22 was used as a reactant, to obtain the desired compound 9.3 g.

HRMS [M] < + >: 730.27

[ Synthetic example  156] Synthesis of Mat 156

The procedure of Synthesis Example 3 was repeated except that 13,13-diphenyl-7,13-dihydrochromeno [2,3-b] carbazole obtained in Preparation Example 23 was used as a reactant, to obtain the title compound 8.5 g; HRMS [M] < + >: 615.26

[ Synthetic example  157] Synthesis of Mat 157

The procedure of Synthesis Example 8 was repeated except that 13,13-diphenyl-7,13-dihydrochromeno [2,3-b] carbazole obtained in Preparation Example 23 was used as a reactant, to obtain the desired compound 4.2 g.

HRMS [M] < + >: 654.24

[ Synthetic example  158] Synthesis of Mat 158

The same procedure as in Synthesis Example 9 was carried out except that 13,13-diphenyl-7,13-dihydrochromeno [2,3-b] carbazole obtained in Preparation Example 23 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 730.27

[ Synthetic example  159] Synthesis of Mat 159

The procedure of Synthesis Example 3 was repeated except that 13,13-diphenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 24 was used as a reactant, to obtain 8 g ≪ / RTI >

HRMS [M] < + >: 615.26

[ Synthetic example  160] Synthesis of Mat 160

The procedure of Synthetic Example 8 was repeated except that 13,13-diphenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 24 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 654.24

[ Synthetic example  161] Synthesis of Mat 161

The same procedure as in Synthesis Example 9 was carried out except that 13,13-diphenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 24 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 730.27

[ Synthetic example  162 Synthesis of Mat 162

The procedure of Synthesis Example 3 was repeated except that 13,13-diphenyl-12,13-dihydrothiochromeno [3,2-a] carbazole obtained in Preparation Example 25 was used as a reactant, 10 g.

HRMS [M] < + >: 631.24

[ Synthetic example  163] Synthesis of Mat 163

The procedure of Synthetic Example 8 was repeated except that the 13,13-diphenyl-12,13-dihydrothiochromeno [3,2-a] carbazole obtained in Preparation Example 25 was used as a reactant, 7 g.

HRMS [M] < + >: 670.22

[ Synthetic example  164] Synthesis of Mat 164

The procedure of Synthesis Example 9 was repeated except that 13,13-diphenyl-12,13-dihydrothiochromeno [3,2-a] carbazole obtained in Preparation Example 25 was used as a reactant, 7 g.

HRMS [M] < + >: 746.25

[ Synthetic example  165 Synthesis of Mat 165

The procedure of Synthesis Example 3 was repeated except that 13,13-diphenyl-11,13-dihydrothiochromeno [3,2-b] carbazole obtained in Preparation Example 26 was used as a reactant, 6 g.

HRMS [M] < + >: 631.24

[ Synthetic example  166] Synthesis of Mat 166

The procedure of Synthetic Example 8 was repeated except that 13,13-diphenyl-11,13-dihydrothiochromeno [3,2-b] carbazole obtained in Preparation Example 26 was used as a reactant, 5 g.

HRMS [M] < + >: 670.22

[ Synthetic example  167] Synthesis of Mat 167

The procedure of Synthesis Example 9 was repeated except that 13,13-diphenyl-11,13-dihydrothiochromeno [3,2-b] carbazole obtained in Preparation Example 26 was used as a reactant, 9g.

HRMS [M] < + >: 746.25

[ Synthetic example  168] Synthesis of Mat 168

The procedure of Synthesis Example 3 was repeated except that 8,8-diphenyl-5,8-dihydrothiochromeno [3,2-c] carbazole obtained in Preparation Example 27 was used as a reactant, 5 g.

HRMS [M] < + >: 631.24

[ Synthetic example  169] Synthesis of Mat 169

The procedure of Synthetic Example 8 was repeated except that 8,8-diphenyl-5,8-dihydrothiochromeno [3,2-c] carbazole obtained in Preparation Example 27 was used as a reactant, 6 g.

HRMS [M] < + >: 670.22

[ Synthetic example  170] Synthesis of Mat 170

The procedure of Synthesis Example 9 was repeated except that 8,8-diphenyl-5,8-dihydrothiochromeno [3,2-c] carbazole obtained in Preparation Example 27 was used as a reactant, 3 g.

HRMS [M] < + >: 746.25

[ Synthetic example  171] Synthesis of Mat 171

The procedure of Synthesis Example 3 was repeated except that 7,7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 28 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 631.24

[ Synthetic example  172] Synthesis of Mat 172

The same procedure as in Synthesis Example 8 was carried out except that 7,7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 28 was used as a reactant, to obtain 9 g ≪ / RTI >

HRMS [M] < + >: 670.22

[ Synthetic example  173] Synthesis of Mat 173

The procedure of Synthesis Example 9 was repeated except that 7,7-phenyl-7,13-dihydrothiochromeno [2,3-a] carbazole obtained in Preparation Example 28 was used as a reactant, to obtain the desired compound 8.7 g.

HRMS [M] < + >: 746.25

[ Synthetic example  174] Synthesis of Mat 174

The procedure of Synthesis Example 3 was repeated except that 13,13-diphenyl-7,13-dihydrothiochromeno [2,3-b] carbazole obtained in Preparation Example 29 was used as a reactant, 4.9 g.

HRMS [M] < + >: 631.24

[ Synthetic example  175] Synthesis of Mat 175

The procedure of Synthetic Example 8 was repeated except that 13,13-diphenyl-7,13-dihydrothiochromeno [2,3-b] carbazole obtained in Preparation Example 29 was used as a reactant, 6.3 g was obtained.

HRMS [M] < + >: 670.22

[ Synthetic example  176] Synthesis of Mat 176

The procedure of Synthesis Example 9 was repeated except that 13,13-diphenyl-7,13-dihydrothiochromeno [2,3-b] carbazole obtained in Preparation Example 29 was used as a reactant, 5.5 g.

HRMS [M] < + >: 746.25

[ Synthetic example  177] Synthesis of Mat 177

The procedure of Synthesis Example 3 was repeated except that 13,13-diphenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 30 was used as a reactant, g.

HRMS [M] < + >: 631.24

[ Synthetic example  178] Synthesis of Mat 178

The procedure of Synthetic Example 8 was repeated except that 13,13-diphenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 30 was used as a reactant, to obtain the desired compound 7.7 g.

HRMS [M] < + >: 670.22

[ Synthetic example  179] Synthesis of Mat 179

The procedure of Synthesis Example 9 was repeated except that 13,13-diphenyl-8,13-dihydrochromeno [2,3-c] carbazole obtained in Preparation Example 30 was used as a reactant, to obtain the desired compound 8.2 g.

HRMS [M] < + >: 746.25

[ Synthetic example  179] Synthesis of Mat 179

The same procedure as in Synthesis Example 3 was carried out except that 5,13,13-triphenyl-12,13-dihydro-5H-indolo [2,3-a] To obtain 10 g of the target compound.

HRMS [M] < + >: 690.30

[ Synthetic example  181] Synthesis of Mat 181

The same procedure as in Synthesis Example 8 was carried out except that 5,13,13-triphenyl-12,13-dihydro-5H-indolo [2,3-a] To obtain 5 g of the aimed compound.

HRMS [M] < + >: 729.29

[ Synthetic example  182] Synthesis of Mat 182

The same procedure as in Synthesis Example 9 was carried out except that 5,13,13-triphenyl-12,13-dihydro-5H-indolo [2,3-a] To obtain 8 g of the target compound.

HRMS [M] < + >: 805.32

[ Synthetic example  183] Synthesis of Mat 183

The same procedure as in Synthesis Example 3 was carried out except that 5,13,13-triphenyl-11,13-dihydro-5H-indolo [2,3-b] To obtain 9 g of the aimed compound.

HRMS [M] < + >: 690.30

[ Synthetic example  184] Synthesis of Mat 184

Except as 5,13,13- obtained in Preparation Example 32 by reaction of triphenyl -11,13- dihydro -5H- indole was used to form the [2,3-b] acridine and the same procedure as in the above Synthesis Example 8 To obtain 6.3 g of the title compound.

HRMS [M] < + >: 729.29

[ Synthetic example  185] Synthesis of Mat 185

Except as 5,13,13- obtained in Preparation Example 32 by reaction of triphenyl -11,13- dihydro -5H- indole was used to form the [2,3-b] acridine The same procedure as in the above Synthesis Example 9 To obtain 5.8 g of the desired compound.

HRMS [M] < + >: 805.32

[ Synthetic example  186] Synthesis of Mat 186

The same procedure as in Synthesis Example 3 was carried out except that 8,8,13-triphenyl-8,13-dihydro-5H-indolo [2,3-c] To obtain 4 g of the target compound.

HRMS [M] < + >: 690.30

[ Synthetic example  187] Synthesis of Mat 187

The same procedure as in Synthesis Example 8 was carried out except that 8,8,13-triphenyl-8,13-dihydro-5H-indolo [2,3-c] To obtain 7 g of the target compound.

HRMS [M] < + >: 729.29

[ Synthetic example  188] Synthesis of Mat 188

The same procedure as in Synthesis Example 9 was carried out except that 8,8,13-triphenyl-8,13-dihydro-5H-indolo [2,3-c] To obtain the desired compound (5.5 g).

HRMS [M] < + >: 805.32

[ Synthetic example  189] Synthesis of Mat 189

The same procedure as in Synthesis Example 3 was repeated except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] The same procedure was followed to obtain 5 g of the target compound.

HRMS [M] < + >: 690.30

[ Synthetic example  190] Synthesis of Mat 190

The same procedure as in Synthesis Example 8 was repeated except for using 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2-c] The same procedure was followed to obtain 9 g of the target compound.

HRMS [M] < + >: 729.29

[ Synthetic example  191] Synthesis of Mat 191

The reaction was carried out in the same manner as in Synthesis Example 9, except that 7-methyl-7,12-diphenyl-12,13-dihydro-7H-indolo [3,2- c] The same procedure was followed to obtain 4.3 g of the target compound.

HRMS [M] < + >: 805.32

[ Synthetic example  192] Synthesis of Mat 192

The same procedure as in Synthesis Example 3 was carried out except that 5,13,13-triphenyl-7,13-dihydro-5H-indolo [3,2-b] To obtain 2.9 g of the desired compound.

HRMS [M] < + >: 690.30

[ Synthetic example  193] Synthesis of Mat 193

The procedure of Synthesis Example 8 was repeated except that 5,13,13-triphenyl-7,13-dihydro-5H-indolo [3,2-b] To obtain 4.8 g of the desired compound.

HRMS [M] < + >: 729.29

[ Synthetic example  194] Synthesis of Mat 194

The same procedure as in Synthesis Example 9 was carried out except that 5,13,13-triphenyl-7,13-dihydro-5H-indolo [3,2-b] To obtain 6.6 g of the desired compound.

HRMS [M] < + >: 805.32

[ Synthetic example  195] Synthesis of Mat 195

The same procedure as in Synthesis Example 3 was carried out except that 5,13,13-triphenyl-8,13-dihydro-5H-indolo [3,2-a] To obtain 7.4 g of the objective compound.

HRMS [M] < + >: 690.30

[ Synthetic example  196] Synthesis of Mat 196

The procedure of Synthesis Example 8 was repeated except that 5,13,13-triphenyl-8,13-dihydro-5H-indolo [3,2-a] To obtain 6.9 g of the desired compound.

HRMS [M] < + >: 729.29

[ Synthetic example  197] Synthesis of Mat 197

The same procedure as in Synthesis Example 9 was carried out except that 5,13,13-triphenyl-8,13-dihydro-5H-indolo [3,2-a] To obtain 3.9 g of the desired compound.

HRMS [M] < + >: 805.32

[ Synthetic example  198] Synthesis of Mat 198

The procedure of Synthesis Example 3 was repeated except that 11H-spiro [chromene [3,2-b] carbazole-13,9'-fluorene] obtained in Preparation Example 37 was used as a reactant, g.

HRMS [M] < + >: 613.24

[ Synthetic example  199] Synthesis of Mat 199

The procedure of Synthesis Example 8 was repeated except that 11H-spiro [chromeno [3,2-b] carbazole-13,9'-fluorene] obtained in Preparation Example 37 was used as a reactant, to obtain the desired compound 5.9 g.

HRMS [M] < + >: 652.23

[ Synthetic example  200] Synthesis of Mat 200

The same procedure as in Synthesis Example 9 was carried out except that 11H-spiro [chromeno [3,2-b] carbazole-13,9'-fluorene] obtained in Preparation Example 37 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 728.26

[ Synthetic example  201] Synthesis of Mat 201

The same procedure as in Synthesis Example 3 was carried out except that 5H-spiro [chromeno [3,2-c] carbazole-8,9'-fluorene] obtained in Preparation Example 38 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 613.24

[ Synthetic example  202] Synthesis of Mat 202

The same procedure as in Synthesis Example 8 was carried out except that 5H-spiro [chromeno [3,2-c] carbazole-8,9'-fluorene] obtained in Preparation Example 38 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 652.23

[ Synthetic example  203] Synthesis of Mat 203

The same procedure as in Synthesis Example 9 was carried out except that 5H-spiro [chromene [3,2-c] carbazole-8,9'-fluorene] obtained in Preparation Example 38 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 728.26

[ Synthetic example  204] Synthesis of Mat 204

The same procedure as in Synthesis Example 3 was carried out except that 13H-spiro [chromeno [2,3-a] carbazole-7,9'-fluorene] obtained in Preparation Example 39 was used as a reactant, g.

HRMS [M] < + >: 613.24

[ Synthetic example  205] Synthesis of Mat 205

The procedure of Synthetic Example 8 was repeated except that 13H-spiro [chromeno [2,3-a] carbazole-7,9'-fluorene] obtained in Preparation Example 39 was used as a reactant, ≪ / RTI >

HRMS [M] < + >: 652.23

[ Synthetic example  206] Synthesis of Mat 206

The same procedure as in Synthesis Example 9 was carried out except that 13H-spiro [chromeno [2,3-a] carbazole-7,9'-fluorene] obtained in Preparation Example 39 was used as a reactant, g.

HRMS [M] < + >: 728.26

[ Synthetic example  207] Synthesis of Mat 207

The procedure of Synthesis Example 3 was repeated except that 7H-spiro [chromeno [2,3-b] carbazole-13,9'-fluorene] obtained in Preparation Example 40 was used as a reactant, to obtain the desired compound 4.6 g.

HRMS [M] < + >: 613.24

[ Synthetic example  208] Synthesis of Mat 208

The same procedure as in Synthesis Example 8 was carried out except that 7H-spiro [chromeno [2,3-b] carbazole-13,9'-fluorene] obtained in Preparation Example 40 was used as a reactant, g.

HRMS [M] < + >: 652.23

[ Synthetic example  209] Synthesis of Mat 209

The same procedure as in Synthesis Example 9 was carried out except that 7H-spiro [chromeno [2,3-b] carbazole-13,9'-fluorene] obtained in Preparation Example 40 was used as a reactant, g.

HRMS [M] < + >: 728.26

[ Synthetic example  210] Synthesis of Mat 210

The procedure of Synthesis Example 3 was repeated except that 11'H-spiro [fluorene-9,13'-thiochromeno [3,2-b] carbazole] was used as a reaction substance in Preparation Example 41, 7.5 g of the compound was obtained.

HRMS [M] < + >: 629.22

[ Synthetic example  211] Synthesis of Mat 211

The same procedure as in Synthesis Example 8 was carried out except that 11'H-spiro [fluorene-9,13'-thiochromeno [3,2-b] carbazole] was used as a reaction mixture in Preparation Example 41, 7.6 g of a compound was obtained.

HRMS [M] < + >: 668.20

[ Synthetic example  212] Synthesis of Mat 212

The procedure of Synthesis Example 9 was repeated except that 11'H-spiro [fluorene-9,13'-thiochromeno [3,2-b] carbazole] was used as a reaction substance in Preparation Example 41, 7 g of a compound was obtained.

HRMS [M] < + >: 744.23

[ Synthetic example  213] Synthesis of Mat 213

The same procedure as in Synthesis Example 3 was carried out except that 5'H-spiro [fluorene-9,8'-thiochromeno [3,2-c] carbazole] obtained in Preparation Example 42 was used as a reactant 10.2 g of the aimed compound was obtained.

HRMS [M] < + >: 629.22

[ Synthetic example  214] Synthesis of Mat 214

The same procedure as in Synthesis Example 8 was carried out except that 5'H-spiro [fluorene-9,8'-thiochromeno [3,2-c] carbazole] obtained in Preparation Example 42 was used as a reactant 12 g of the aimed compound was obtained.

HRMS [M] < + >: 668.20

[ Synthetic example  215] Synthesis of Mat 215

The same procedure as in Synthesis Example 9 was carried out except that 5'H-spiro [fluorene-9,8'-thiochromeno [3,2-c] carbazole] obtained in Preparation Example 42 was used as a reactant 9 g of the objective compound was obtained.

HRMS [M] < + >: 744.23

[ Synthetic example  216] Synthesis of Mat 216

The same procedure as in Synthesis Example 3 was carried out except that 13'H-spiro [fluorene-9,7'-thiocromeno [2,3-a] carbazole] obtained in Preparation Example 43 was used as a reactant, 9.2 g of the intended compound was obtained.

HRMS [M] < + >: 629.22

[ Synthetic example  217] Synthesis of Mat 217

The same procedure as in Synthesis Example 8 was carried out except that 13'H-spiro [fluorene-9,7'-thiochromeno [2,3-a] carbazole] obtained in Preparation Example 43 was used as a reactant, To obtain 6.9 g of the desired compound.

HRMS [M] < + >: 668.20

[ Synthetic example  218] Synthesis of Mat 218

The same procedure as in Synthesis Example 9 was carried out except that 13'H-spiro [fluorene-9,7'-thiocromeno [2,3-a] carbazole] obtained in Preparation Example 43 was used as a reactant, 7.7 g of the objective compound was obtained.

HRMS [M] < + >: 744.23

[ Synthetic example  219] Synthesis of Mat 219

The procedure of Synthesis Example 3 was repeated except that 7'H-spiro [fluorene-9,13'-thiochromeno [2,3-b] carbazole] obtained in Preparation Example 44 was used as a reactant, To obtain 6.9 g of the desired compound.

HRMS [M] < + >: 629.22

[ Synthetic example  220] Synthesis of Mat 220

The same procedure as in Synthesis Example 8 was carried out except that 7'H-spiro [fluorene-9,13'-thiochromeno [2,3-b] carbazole] obtained in Preparation Example 44 was used as a reactant, 7.2 g of the desired compound was obtained.

HRMS [M] < + >: 668.20

[ Synthetic example  221] Synthesis of Mat 221

The procedure of Synthesis Example 9 was repeated except that 7'H-spiro [fluorene-9,13'-thiochromeno [2,3-b] carbazole] obtained in Preparation Example 44 was used as a reactant, 8.8 g of the desired compound was obtained.

HRMS [M] < + >: 744.23

[ Synthetic example  222] Synthesis of Mat 222

Except that 5'-phenyl-5 ', 11'-dihydrospiro [fluorene-9,13'-indolo [2,3-b] acridine] obtained in Preparation Example 45 was used as a reactant. The procedure of Synthesis Example 3 was repeated to obtain 9.2 g of the target compound.

HRMS [M] < + >: 688.29

[ Synthetic example  223] Synthesis of Mat 223

Except that 5'-phenyl-5 ', 11'-dihydrospiro [fluorene-9,13'-indolo [2,3-b] acridine] obtained in Preparation Example 45 was used as a reactant. The procedure of Synthesis Example 8 was repeated to yield the desired compound (4.6 g).

HRMS [M] < + >: 727.27

[ Synthetic example  224] Synthesis of Mat 224

Except that 5'-phenyl-5 ', 11'-dihydrospiro [fluorene-9,13'-indolo [2,3-b] acridine] obtained in Preparation Example 45 was used as a reactant. The procedure of Synthesis Example 9 was repeated to obtain 4 g of the target compound.

HRMS [M] < + >: 803.30

[ Synthetic example  225] Synthesis of Mat 225

Except that 13'-phenyl-5 ', 13'-dihydrospiro [fluorene-9,8'-indolo [2,3-c] acridine] obtained in Preparation Example 46 was used as a reactant. The procedure of Synthesis Example 3 was repeated to obtain 8 g of the target compound.

HRMS [M] < + >: 688.29

[ Synthetic example  226] Synthesis of Mat 226

Except that 13'-phenyl-5 ', 13'-dihydrospiro [fluorene-9,8'-indolo [2,3-c] acridine] obtained in Preparation Example 46 was used as a reactant. The procedure of Synthesis Example 8 was repeated to obtain 6 g of the target compound.

HRMS [M] < + >: 727.27

[ Synthetic example  227] Synthesis of Mat 227

Except that 13'-phenyl-5 ', 13'-dihydrospiro [fluorene-9,8'-indolo [2,3-c] acridine] obtained in Preparation Example 46 was used as a reactant. The procedure of Synthesis Example 9 was repeated to obtain 6.3 g of the target compound.

HRMS [M] < + >: 803.30

[ Synthetic example  228] Synthesis of Mat 228

Except that 12'-phenyl-12 ', 13'-dihydrospiro [fluorene-9,7'-indolo [3,2-c] acridine] obtained in Preparation Example 47 was used as a reactant. The procedure of Synthesis Example 3 was repeated to obtain 5 g of the target compound.

HRMS [M] < + >: 688.29

[ Synthetic example  229] Synthesis of Mat 229

Except that 12'-phenyl-12 ', 13'-dihydrospiro [fluorene-9,7'-indolo [3,2-c] acridine] obtained in Preparation Example 47 was used as a reactant. The procedure of Synthesis Example 8 was repeated to obtain 4 g of the target compound.

HRMS [M] < + >: 727.27

[ Synthetic example  230] Synthesis of Mat 230

Except that 12'-phenyl-12 ', 13'-dihydrospiro [fluorene-9,7'-indolo [3,2-c] acridine] obtained in Preparation Example 47 was used as a reactant. The procedure of Synthesis Example 9 was repeated to obtain 9 g of the target compound.

HRMS [M] < + >: 803.30

[ Synthetic example  231] Synthesis of Mat 231

Except that 5'-phenyl-5 ', 7'-dihydrospiro [fluorene-9,13'-indolo [3,2-b] acridine] obtained in Preparation Example 48 was used as a reactant. The procedure of Synthesis Example 3 was repeated to obtain 3 g of the target compound.

HRMS [M] < + >: 688.29

[ Synthetic example  232] Synthesis of Mat 232

Except that 5'-phenyl-5 ', 7'-dihydrospiro [fluorene-9,13'-indolo [3,2-b] acridine] obtained in Preparation Example 48 was used as a reactant. The procedure of Synthesis Example 8 was repeated to obtain the title compound (4.5 g).

HRMS [M] < + >: 727.27

[ Synthetic example  233] Synthesis of Mat 233

Except that 5'-phenyl-5 ', 7'-dihydrospiro [fluorene-9,13'-indolo [3,2-b] acridine] obtained in Preparation Example 48 was used as a reactant. The procedure of Synthesis Example 9 was repeated to obtain 6.5 g of the target compound.

HRMS [M] < + >: 803.30

[ Example  1 ~ 34] Green organic Field  Manufacturing of light emitting device

Compounds Mat 1 to Mat 233 synthesized in Synthesis Examples 1 to 233 were subjected to high purity sublimation purification by a conventionally known method, and a green organic electroluminescent device was fabricated according to the following procedure.

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

M-MTDATA (60 nm) / TCTA (80 nm) / compound 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

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

A green organic EL device was fabricated in the same manner as in Example 1, except that CBP was used instead of the compound Mat 3 as a luminescent host material in forming the light emitting layer.

[ Evaluation example  One]

Current efficiency and emission peak at current density (10) mA / cm < 2 > were measured for each of the green organic electroluminescent devices manufactured in Examples 1 to 34 and Comparative Example 1, Respectively.

Sample Host The driving voltage (V) EL peak (nm) Current efficiency (cd / A) Example 1 Mat 3 6.85 516 42 Example 2 Mat 7 6.95 515 39.8 Example 3 Mat 8 6.78 516 39.5 Example 4 Mat 9 6.74 516 41.1 Example 5 Mat 10 6.88 516 40.5 Example 6 Mat 14 6.82 515 39.5 Example 7 Mat 20 6.9 516 41 Example 8 Mat 21 6.76 516 40.2 Example 9 Mat 29 6.78 516 42 Example 10 Mat 30 6.78 515 39.8 Example 11 Mat 37 6.74 516 39.5 Example 12 Mat 39 6.78 516 41.1 Example 13 Mat 45 6.74 516 40.5 Example 14 Mat 47 6.88 515 39.5 Example 15 Mat 56 6.82 516 41 Example 16 Mat 72 6.9 516 40.2 Example 17 Mat 78 6.76 516 42 Example 18 Mat 86 6.78 515 39.8 Example 19 Mat 93 6.74 516 39.5 Example 20 Mat 108 6.88 516 41.1 Example 21 Mat 120 6.78 516 40.5 Example 22 Mat 127 6.78 515 42 Example 23 Mat 134 6.78 516 39.8 Example 24 Mat 135 6.74 516 39.5 Example 25 Mat 146 6.88 516 41.1 Example 26 Mat 155 6.82 515 40.5 Example 27 Mat 158 6.9 516 39.5 Example 28 Mat 167 6.76 516 41 Example 29 Mat 182 6.78 516 40.2 Example 30 Mat 197 6.74 515 39.8 Example 31 Mat 212 6.88 516 40.5 Example 32 Mat 218 6.88 516 39.5 Example 33 Mat 227 6.9 516 41 Example 34 Mat 233 6.88 516 40.2 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound (Mat 3 to Mat 233) according to the present invention was used as a light emitting layer of a green organic electroluminescent device (Examples 1 to 34), a green organic electroluminescent device using conventional CBP It can be seen that it shows better performance in terms of efficiency and driving voltage as compared with Example 1).

[ Example  35 ~ 58] Red organic Field  Manufacturing of light emitting device

The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a red organic electroluminescent device was fabricated according to the following procedure.

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

M-MTDATA (60 nm) / TCTA (80 nm) / compound described in Table 2 + 10% (piq) ₂ Ir (acac) (30 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.

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

A red organic electroluminescent device was fabricated in the same manner as in Example 35 except that CBP was used instead of the compound of Mat 4 as a luminescent host material in the formation of the light emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 35 to 58 and Comparative Example 2 are as follows.

[ Evaluation example  2]

The driving voltage and the current efficiency at a current density of 10 mA / cm 2 were measured for each of the organic electroluminescent devices manufactured in Examples 35 to 58 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 35 Mat 4 5.12 8.7 Example 36 Mat 5 4.89 8.6 Example 37 Mat 8 5.11 8.8 Example 38 Mat 9 4.89 8.6 Example 39 Mat 17 5.12 9.3 Example 40 Mat 19 4.89 8.7 Example 41 Mat 28 4.97 8.6 Example 42 Mat 35 4.97 8.6 Example 43 Mat 44 5.02 9.2 Example 44 Mat 68 4.89 9.5 Example 45 Mat 75 4.97 9.45 Example 46 Mat 77 4.92 9.5 Example 47 Mat 89 4.98 8.7 Example 48 Mat 110 4.98 9.0 Example 49 Mat 117 5.12 8.6 Example 50 Mat 126 5.12 9.3 Example 51 Mat 133 4.89 9.5 Example 52 Mat 138 4.92 8.6 Example 53 Mat 145 4.88 9.3 Example 54 Mat 187 5.12 9.5 Example 55 Mat 196 4.89 8.6 Example 56 Mat 211 4.92 9.2 Example 57 Mat 220 4.88 9.5 Example 58 Mat 232 4.98 9.45 Comparative Example 2 CBP 5.25 8.2

As shown in Table 2, when the compound according to the present invention was used as a material of the light emitting layer of the red organic electroluminescent device (Examples 35 to 58), the red light emitting organic electroluminescent device using conventional CBP as the material of the light emitting layer 2), it can be seen that it shows excellent performance in terms of efficiency and driving voltage.

[ Example  59 ~ 66] Organic Field  Manufacturing of light emitting device

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), and the substrate was cleaned using UV for 5 minutes And the substrate was transferred to the back vacuum deposition machine.

M-MTDATA (60 nm) / compound (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq ₃ An organic electroluminescent device was fabricated in the order of LiF (1 nm) / Al (200 nm).

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

[ Comparative Example  3] Organic Field  Manufacturing of light emitting device

An organic electroluminescent device was prepared in the same manner as in Example 59 except that NPB was used as a hole transport layer material instead of the compound Mat 11 used as a hole transport layer material in forming the hole transport layer in Example 59. The structure of the NPB used is as follows.

[ Evaluation example  3]

The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 59 to 66 and Comparative Example 3, respectively, and the results are shown in Table 3 below.

Sample Hole transport layer The driving voltage (V) Current efficiency (cd / A) Example 59 Mat 11 4.86 18.7 Example 60 Mat 23 4.8 18.7 Example 61 Mat 31 4.98 18.6 Example 62 Mat 58 4.92 18.5 Example 63 Mat 73 4.89 18.8 Example 64 Mat 87 4.8 18.5 Example 65 Mat 115 4.9 18.6 Example 66 Mat 129 4.9 18.5 Comparative Example 3 NPB 5.2 18.1

As shown in the above Table 3, the organic electroluminescent devices using the compounds (Mat 11 to Mat 129) according to the present invention as the hole transport layer (organic electroluminescent devices manufactured respectively in Examples 59 to 56) The organic EL device of Comparative Example 3 exhibited better current efficiency and better driving voltage than the organic electroluminescent device (organic EL device of Comparative Example 3).

Claims (14)

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

(2)

In the above formulas (1) and (2)
At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ is condensed with the ring represented by Formula 2 to form a condensed ring;
The dotted line is the part where the condensation occurs;
X ₁ and X ₂ are each independently O, S, Se, N ( Ar 3), C (Ar 4) (Ar 5) and Si (Ar ₆₎ is selected from the group consisting of (Ar _7), wherein X ₂ Lt; / RTI > are the same or different;
A ₁ to A ₈ are each independently N or C (R ₅ );
And R ₁ to R ₄ do not form a ring and a condensed ring represented by the formula 2, R ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ an alkenyl group of C _40, C ₂ ~ C ₄₀ of the alkynyl group, 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 of the C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ aryl groups, alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ And each adjacent R ₅ may combine with each other to form a condensed ring. When a plurality of R _{5 s} are present, they may be the same or different;
Ar ₁ to Ar ₇ each independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, C ₆ to C ₆₀ aryloxy groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ aryl groups, An arylsilyl group of C ₆ to C ₆₀ , 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 A mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, or Ar ₁ and Ar ₂ may combine with each other to form a condensed ring, and Ar ₂ to Ar ₆ When there are a plurality of each of them, they are the same as or different from each other;
The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group of R ₁ to R ₅ and Ar ₁ to Ar ₇ A boron group, an arylphosphine group, a mono or diarylphosphinyl group, and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ alkynyl group, ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C substituted with at least ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl amine of the selected one or more substituents being unsubstituted, When 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 3 to 8:
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

In the above Chemical Formulas 3 to 8,
X ₁ , X ₂ , Ar ₁ , Ar ₂ and A ₁ to A ₈ are the same as defined in the above formulas (1) and (2). The method according to claim 1,
Wherein the compound represented by Formula 1 is a compound represented by Formula 9:
[Chemical Formula 9]

(2)

In the above formulas (2) and (9)
At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ is condensed with the ring represented by Formula 2 to form a condensed ring;
The dotted line is the part where the condensation occurs;
X ₁ and X ₂ are each independently O, S, Se, N ( Ar 3), C (Ar 4) (Ar 5) and Si (Ar ₆₎ is selected from the group consisting of (Ar _7), wherein X ₂ Lt; / RTI > are the same or different;
A ₁ to A ₁₃ are each independently N or C (R ₅ );
And R ₁ to R ₄ do not form a ring and a condensed ring represented by the formula 2, R ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ an alkenyl group of C _40, C ₂ ~ C ₄₀ of the alkynyl group, 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 of the C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ aryl groups, alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ And each adjacent R ₅ may combine with each other to form a condensed ring. When a plurality of R _{5 s} are present, they may be the same or different;
Ar ₁ and Ar ₃ to Ar ₇ each independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, an aryloxy group of a C ₆ ~ C _60, C ₃ -aryl silyl group of C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ of, C ₁ - C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ aryl phosphine group, C ₆ of the C ₆₀ mono-or diaryl phosphine of C ₆₀ P is selected from the group the group consisting of C ₆ - C ₆₀ aryl amine, wherein Ar ₃ to Ar ₇ When there are a plurality of each of them, they are the same as or different from each other;
The R ₁ to R ₅ , Ar ₁ And an alkyl group of Ar ₃ to Ar ₇ , a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, , The mono or diarylphosphinyl group and the arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₆₀ aryloxy A C ₃ to C ₄₀ alkylsilyl group, a C ₆ to C ₆₀ arylsilyl group, a C ₁ to C ₄₀ alkylboron group, a C ₆ to C ₆₀ arylboron group, a C ₆ to C ₆₀ arylphosphine pingi, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ substituted by one or more substituents selected from the group consisting of C ₆₀ aryl amine, or unsubstituted, and the plurality of substitution Case be substituted with these may be the same or different from each other. The method according to claim 1,
Wherein the compound represented by Formula 1 is a compound represented by Formula 10:
[Chemical formula 10]

(2)

In the above formulas (2) and (10)
At least one of R ₁ and R ₂ , R ₂ and R _3, and R ₃ and R ₄ is condensed with the ring represented by Formula 2 to form a condensed ring;
The dotted line is the part where the condensation occurs;
X ₁ and X ₂ are each independently O, S, Se, N ( Ar 3), C (Ar 4) (Ar 5) and Si (Ar ₆₎ is selected from the group consisting of (Ar _7), wherein X ₂ Lt; / RTI > are the same or different;
A ₁ to A ₈ and A ₁₄ to A ₂₁ are each independently N or C (R ₅ );
And R ₁ to R ₄ do not form a ring and a condensed ring represented by the formula 2, R ₅ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ an alkenyl group of C _40, C ₂ ~ C ₄₀ of the alkynyl group, 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 of the C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ alkylsilyl groups, C ₆ to C ₆₀ arylsilyl groups, C ₁ to C ₄₀ aryl groups, alkyl boron group, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ mono or diaryl phosphine of C ₆₀ blood group and a C ₆ ~ the group consisting of an aryl amine of the C ₆₀ And each adjacent R ₅ may combine with each other to form a condensed ring. When a plurality of R _{5 s} are present, they may be the same or different;
Ar ₃ to Ar ₇ each independently represent a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ cycloalkyl group, C ₆ to C ₆₀ aryloxy groups, 5 to 60 heteroaryl groups, C ₁ to C ₄₀ alkyloxy groups, C ₆ to C ₆₀ aryloxy groups, C ₃ to C ₄₀ aryl groups, An arylsilyl group of C ₆ to C ₆₀ , 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 A mono or diarylphosphinyl group and a C ₆ to C ₆₀ arylamine group, and Ar ₃ to Ar ₇ When there are a plurality of each of them, they are the same as or different from each other;
The alkyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, aryl group and aryl group of R ₁ to R ₅ and Ar ₃ to Ar ₇ A boron group, an arylphosphine group, a mono or diarylphosphinyl group, and an arylamine group are each independently a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₃ to C ₄₀ alkynyl group, ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C ₁ ~ alkyloxy group of C _40, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, a alkyl boronic of C ₁ ~ C _40, an aryl boronic a C ₆ ~ C _60, C ₆ ~ C substituted with at least ₆₀ of the aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine group P and the group consisting of C ₆ ~ C ₆₀ aryl amine of the selected one or more substituents being unsubstituted, When substituted with a plurality of substituents, they may be the same or different. The method according to claim 1,
X ₁ and X ₂ are each independently selected from the group consisting of O, S, and N (Ar ₃ )
Each of Ar ₁ and Ar ₂ is independently a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, and a substituted or unsubstituted five to sixty And Ar ₁ and Ar ₂ are bonded to each other to form a substituted or unsubstituted C ₆ to C ₆₀ condensed aromatic ring,
Ar ₃ is an aryl group having ₆ to ₆₀ carbon atoms or a heteroaryl group having 5 to 60 nuclear atoms,
The aryl group and the heteroaryl group of Ar ₃ are each independently substituted with at least one substituent selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms And when they are substituted with a plurality of substituents, they are the same or different from each other. 6. The method of claim 5,
Wherein Ar ₁ and Ar ₂ are each independently selected from the group consisting of a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group and a substituted or unsubstituted phenyl group, or Ar ₁ and Ar ₂ are bonded to each other to form a fluorene structure Lt; / RTI >
Ar ₃ may be selected from the group consisting of phenyl, biphenyl and fluorene,
The phenyl, biphenyl and fluorene of Ar ₃ are each independently a methyl group, an ethyl group, a phenyl group, a biphenyl group, a triphenylene group, or an imidazolyl group. A carbazolyl group and a dibenzothiophenyl group, and when they are substituted with a plurality of substituents, they are the same as or different from each other. The method according to claim 1,
Wherein at least one of R ₅ and Ar ₁ to Ar ₇ is a substituent represented by the following formula (11) or a phenyl group:
(11)

In Formula 11,
* Means a moiety bonded to Formula 1 or Formula 2;
L ₁ is 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;
Z ₁ to Z ₅ are each independently N or C (R ₆ ), or at least one of Z ₁ to Z ₅ is N;
R ₆ is 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 ~ C ₆₀ of the aryl group, 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 number of nuclear atoms of 3 to 40 heterocycloalkyl group , An arylamine group of C ₆ to C ₆₀ , 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 , 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, or the group bonded to the adjacent, may form a condensed ring, a plurality of individual said R ₆ They are the same or different from each other;
Arylene group and a heteroarylene group, an alkyl group of the R ₆ of said L _1, 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, A halogen atom, a cyano group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ of the 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 ~ C _A C ₃ to C ₄₀ cycloalkyl group, a cyclohexyl group having 3 to 40 nuclear atoms, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, ₄₀ alkyl group of boron, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ aryl yarn And when they are substituted with a plurality of substituents, they may be the same as or different from each other. 8. The method of claim 7,
The substituent represented by the formula (11) is a substituent represented by any one of the following A-1 to A-15:

In the above A-1 to A-15,
n is an integer of 0 to 4, and when n is 0, hydrogen means that hydrogen is not substituted with substituent R ₇ ; when n is an integer of 1 to 4, R ₇ is deuterium, halogen, cyano, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, C ₆ of ~ 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 arylamine group of ₆ ~ C _60, C ₁ ~ C ₄₀ alkylsilyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C ₄₀ group of the arylboronic, C ₆ ~ mono or diaryl phosphine of C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ of the blood A C ₆ -C ₆₀ arylsilyl group, or may be bonded to an adjacent group to form a condensed ring. When a plurality of R _{7 s} are present, they may be the same or different;
Alkyl group of the R _7, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy 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,
*, L ₁ and R ₆ are as defined in the above formula (11). 8. The method of claim 7,
Wherein L < _{1 >} is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted carbazolyl group,
Wherein R ₆ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms. The method according to claim 1,
Wherein at least one of R ₅ and Ar ₁ to Ar ₇ is a substituent represented by the following formula (12):
[Chemical Formula 12]

In Formula 12,
* Means a moiety bonded to Formula 1 or Formula 2;
L ₂ is 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 ₈ and R ₉ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms and a C ₆ to C ₆₀ arylamine group Or R ₈ and R ₉ may combine to form a condensed ring;
Wherein the L ₂ arylene group and a heteroarylene group, wherein R ₈ and a group of R _9, an aryl group, a heteroaryl group, and aryl amine groups are each independently selected from deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ An alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₆₀ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C ₆ to C ₆₀ aryloxy group, A C ₁ to C ₄₀ alkyloxyl group, a C ₆ to C ₆₀ arylamine group, a C ₃ to C ₄₀ cycloalkyl group, a 3 to 40 nuclear atomic heterocycloalkyl group, a C ₁ to C ₄₀ alkylsilyl group, a C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ 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 ~ C ₆₀ of the Arylsilyl group, and when they are substituted with a plurality of substituents, they may be the same or different from each other. 11. The method of claim 10,
L ₂ is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted carbazolyl group,
Wherein R ₈ and R ₉ are each independently a substituted or unsubstituted C ₆ to C ₆₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 60 ring 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). 14. The method of claim 13,
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 injecting layer, a life improving layer, a light emitting layer, and a light emitting auxiliary layer.