KR101829166B1 - Organic light-emitting compound and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent device having improved luminous efficiency, driving voltage, lifetime and the like by incorporating a novel compound having excellent luminous efficiency into one or more organic layers.

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 dibenzodioxin, thianthrene, phenazine, dihydroanthracene, Xanthanthine, or acridine-based compounds, and to an organic electroluminescent device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by incorporating them into one or more organic layers.

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 luminescence properties, but their glass transition temperature is low and their thermal stability is not very good, which is not satisfactory in terms of lifetime in organic electroluminescent devices.

It is an object of the present invention to provide a novel organic compound which can be applied to an organic electroluminescent device and which 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)

R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R _7, and at least one of R ₇ and R ₈ 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 to X ₃ are each independently selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ is selected from the group consisting of (Ar _5), wherein X ₃ Lt; / RTI > are the same or different;

Each of A ₁ to A ₄ is independently N or C (R ₉ ), and when a plurality of A ₁ to A ₄ are respectively plural, they are the same or different;

Do not form a ring and a condensed ring represented by the general formula 2 R ₁ to R _8, and R ₉ are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, an alkyl group of _{C 1 ~ C 40, 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 when there are a plurality of R < ₉ > s, they are the same as or different from each other;

Ar ₁ to Ar ₅ 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 when Ar ₁ to Ar ₅ are each a plural number, 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 ₉ and Ar ₁ to Ar ₅ 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 they are 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 dibenzodioxin, thianthrene, phenazine, dihydroanthracene, xanthene, thioxanthene or acridine benzene, an indene moiety or an indole moiety moiety is condensed to form a basic skeleton and is represented by the following general formula (1). 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)

R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₅ and R ₆ , R ₆ and R ₇ and at least one of R ₇ and R ₈ , preferably R ₁ and R ₂ , R ₂ and R _3, and one of R ₃ and R ₄ and R ₅ and R ₆ , One of R ₆ and R ₇ and one of R ₇ and R ₈ 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 to X ₃ are each independently selected from O, S, Se, N ( Ar 1), C (Ar 2) (Ar 3) and Si (Ar ₄₎ is selected from the group consisting of (Ar _5), wherein X ₃ Lt; / RTI > are the same or different;

Each of A ₁ to A ₄ is independently N or C (R ₉ ), and when a plurality of A ₁ to A ₄ are respectively plural, they are the same or different;

And R ₁ to R ₈ does not form a ring and a condensed ring represented by the formula 2, R ₉ 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 when there are a plurality of R < ₉ > s, they are the same as or different from each other;

Ar ₁ to Ar ₅ 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 when Ar ₁ to Ar ₅ are each a plural number, 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 ₉ and Ar ₁ to Ar ₅ 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 they are 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 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 the formula (1) may be a compound represented by any one of the following formulas (3) to (5).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above Chemical Formulas 3 to 5,

X ₁ to X ₃ and A ₁ to A ₄ are the same as defined in the above formulas (1) and (2), but two X ₃ may be the same or different and each of A ₁ to A ₄ is also the same Can be different.

According to a preferred embodiment of the present invention, in the compound represented by the general formula (1), Ar ₁ 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 compound represented by the general formula (1), Ar ₁ 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 Formula 1, Ar ₁ is phenyl, biphenyl, terphenyl, dibenzofuranyl, fluorenyl, carbazolyl and dibenzothiophenyl ≪ / RTI >

Wherein said phenyl, biphenyl, terphenyl, dibenzofuranyl, fluorenyl, carbazolyl, and dibenzothiophenyl 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, To 60 heteroaryl groups, which are unsubstituted or substituted with a plurality of substituents, which may be the same or different from each other.

According to a preferred embodiment of the present invention, in the compound represented by Formula 1, Ar ₁ is phenyl, biphenyl, terphenyl, dibenzofuranyl, fluorenyl, carbazolyl and dibenzothiophenyl ≪ / RTI >

Wherein the phenyl, biphenyl, terphenyl, dibenzofuranyl, fluorenyl, carbazolyl and dibenzothiophenyl are each independently selected from the group consisting of methyl, ethyl, phenyl, biphenyl, phenanthrenyl and carbazolyl groups. And when they are substituted with plural substituents, they may be the same or different.

According to a preferred embodiment of the present invention, in the compound represented by Formula 1, Ar ₂ and Ar ₃ each independently represent a substituted or unsubstituted C ₁ to C ₄₀ alkyl group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, or a substituted or unsubstituted 5 to 60 nucleus atoms may be a hetero aryl group.

According to a preferred embodiment of the present invention, in the compound represented by Formula 1, Ar ₂ and Ar ₃ each independently represent a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, Or a substituted or unsubstituted phenyl group.

According to a preferred embodiment of the present invention, at least one of R ₉ and Ar ₁ to Ar ₅ is a substituent represented by the following general formula (6) or a phenyl group.

[Chemical Formula 6]

In Formula 6,

* 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;

Each of Z ₁ to Z ₅ is independently N or C (R ₁₀ ), or at least one of Z ₁ to Z ₅ is N;

R ₁₀ is hydrogen, deuterium, halogen, cyano, nitro, C ₁ to C ₄₀ alkyl, C ₂ to C ₄₀ alkenyl, C ₂ to C ₄₀ alkynyl, C ₆ to C ₆₀ aryl, nuclear atoms of 5 to 60 heteroaryl group, C ₆ ~ C aryloxy ₆₀ C ₁ ~ C ₄₀ alkyloxy group of, C ₃ ~ C ₄₀ cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, A C ₆ to C ₆₀ arylamine group, 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, combined with a C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ selected from the group consisting arylsilyl of C ₆₀ or, or adjacent groups (e.g., L, the other R ₁₀ which are adjacent) to a to a condensed ring Lt; / RTI >

Arylene group and a heteroarylene group, an alkyl group of the R ₁₀ of the 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 group of boron, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine of blood group and a C ₆ ~ C ₆₀ aryl group When substituted by one or more substituents selected from the group consisting of a reel or unsubstituted and ring, which is substituted with plural substituents, they may be the same or different from each other.

According to a preferred embodiment of the present invention, specific examples of the substituent represented by the formula (6) include, but are not limited to, substituents represented by 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 ₁₁ ; when n is an integer of 1 to 4, R ₁₁ 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 group ₆₀ arylboronic of, 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 ₁₀ or other R ₁₁₎ to which they are attached may form a fused ring, wherein the R ₁₁ a plurality If they are individuals, Lt; / RTI >

Alkyl group of the R _11, 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 ₄₀ mono or diaryl phosphine blood group and a C ₆ ~ at least one selected from the group consisting of C ₆₀ arylsilyl of And when they are substituted with a plurality of substituents, they may be the same or different from each other;

*, L < ₁ > and R < ₁₀ >

According to a preferred embodiment of the present invention, in the substituent represented by the general formula (6), R ₁₁ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 60 hetero atoms An aryl group, more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted pyridinyl group.

According to a preferred embodiment of the present invention, at least one of R ₉ and Ar ₁ to Ar ₅ may be a substituent represented by the following general formula (7).

(7)

In Formula 7,

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

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

R ₁₂ and R ₁₃ are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C ₆ ~ selected from the group consisting of an aryl amine of the C ₆₀ of the Or R ₁₂ and R ₁₃ may combine to form a condensed ring;

The alkyl, aryl, heteroaryl and arylamine groups of the L ₂ and the R ₁₂ and R ₁₃ are independently selected from the group consisting of deuterium, halogen, cyano, nitro, C ₁ to 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 alkyloxy 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 as or different from each other.

According to a preferred embodiment of the present invention, in the substituent represented by the general formula (7), R ₁₂ and R ₁₃ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted nuclear atom More preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

In the present invention, the compound represented by Formula 1 may be represented by the following compounds, but is 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 Field  Light emitting element

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

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. a-1 (1,6- Bis (2-nitrophenyl) dibenzo [b, e] [One, 4] dioxin ) Synthesis of

Dibromodibenzo [b, e] [1,4] dioxine (50 g, 146 mmol), (2-nitrophenyl) boronic acid (53.6 g, 321.6 mmol) and K ₂ CO ₃ (100 g, 730 mmol), Pd (PPh 3) 4 (16.8 g, 14.6 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 subjected to column chromatography to obtain 56 g (90%) of the target compound.

GC-Mass (calculated: 426.09 g / mol, measured: 426.38 g / mol)

^{1 H-NMR: 8.06 (m} , 4H), 7.89 (m, 2H), 7.72 (m, 4H), 7.12 (m, 2H), 6.89 (m, 2H)

2. a-2 ( 1H, 9H - [1,4] dioxino [2,3-c: 5,6-c '] dicarbazole ) Synthesis of

Dibenzo [b, e] [1,4] dioxine (56 g, 131 mmol), PPh ₃ (103 g, 394 mmol) and 200 ml of nitrobenzene were placed under a nitrogen stream, And the mixture was refluxed for 8 hours. 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 40 g (85%) of the target compound.

GC-Mass (theory: 362.11 g / mol, measured: 362.39 g / mol)

^{1 H-NMR: 11.66 (bs} , 2H), 8.19 (d, 2H), 7.63 (m, 6H), 7.21 (m, 4H)

3. a-3 (1 - ( [1,1'- biphenyl] -4-yl) - 1H, 9H - [1,4 ] dioxino [2,3-c: 5,6-c '] synthesis of dicarboxylic bar sol)

1H, 9H- [1,4] dioxino [2,3-c: 5,6-c '] dicarbazole and 7.2 g (27.5 mmol) of 4-bromo-1,1'- mmol) was added 250 mL of xylene. 2.5 g (2.75 mmol) of Pd ₂ (dba) ₃ , 2.62 g (5.5 mmol) of Xphos and 6.6 g (68.75 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 9.19 g (yield 65%) of the target compound.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

^{1 H-NMR: 11.2 (bs} , 1H), 7.98 (d, 3H), 7.77 ~ 7.58 (m, 12H), 7.42 (m, 4H), 6.95 (m, 2H)

4. a-4 (1 - ([ 1,1'- biphenyl] -3-yl) - 1H, 9H - [1,4 ] dioxino [2,3-c: 5,6-c '] dicarboxylic bar Sol)

The procedure of Step 3 (a-3) of Preparation Example 1 was repeated except for using 3-bromo-1,1'-biphenyl as a reactant, to obtain 7.4 g of the title compound.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

5. a-5 (1- (4,6- diphenyl-1,3,5-triazin-2-yl) - 1H, 9H - [1,4 ] dioxino [2,3- c: 5 , 6-c '] dicarbazole)

The procedure of Step 3 of Preparation Example 1 was repeated except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used as a reactant, to obtain 6.8 g of the title compound.

GC-Mass (theory: 593.16 g / mol, measured: 593.65 g / mol)

[ Preparation Example  2]

1. b-1 - sum of (N1, N6-bis (2-bromophenyl) dibenzo [b, e] [1, 4] dioxine-1,6-diamine) castle

250 mL of xylene was added to 50 g (146 mmol) of 1,6-dibromodibenzo [b, e] [1,4] dioxine and 27.6 g (160.8 mmol) of 2-bromoaniline. 13.6 g (14.6 mmol) of Pd ₂ (dba) ₃ , 13.9 g (29.2 mmol) of Xphos and 35 g (365 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 52.8 g (yield 69%) of the desired compound.

GC-Mass (calculated: 523.89 g / mol, measured: 524.21 g / mol)

^{1 H-NMR: 9.9 (bs} , 2H), 7.85 (d, 2H), 7.6 ~ 7.48 (m, 10H), 6.55 (m, 2H)

2. b-2 ( 7H, 15H - [1,4] dioxino [2,3-a: 5,6-a '] dicarbazole ) Synthesis of

A stream of nitrogen N1, N6- bis (2-bromophenyl) dibenzo [b, e] [1,4] dioxine-1,6-diamine (50g, 95.7 mmol), Pd (PPh 3) 4 (5.53 g , 4.78 mmol), KOAc (14 g, 143.5 mmol) and 200 ml of DMA were added, and the mixture was refluxed with stirring for 8 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and 29 g (84.8%) of the target compound was obtained by column chromatography.

GC-Mass (theory: 362.11 g / mol, measured: 362.39 g / mol)

¹ H-NMR: 12.01 (bs, 2H), 7.98 (d, 2H), 7.72 (m, 6H)

3. b-3 (1 - ( [1,1'- biphenyl] -4-yl) - 1H, 9H - [1,4 ] dioxino [2,3-c: 5,6-c '] synthesis of dicarboxylic bar sol)

Step 3 (preparation step a-3) of Preparation Example 1 was repeated except that 7H, 15H- [1,4] dioxino [2,3-a: 5,6-a '] dicarbazole was used as a reactant. , The desired compound (7.4 g) was obtained.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

4. b-4 (7- (3- (4,6- diphenyl-1,3,5-triazin-2-yl) phenyl) - 7H, 15H - [1,4 ] dioxino [2, 3-a: 5,6-a '] dicarbazole)

(Step b-3) of Preparation Example 2 except that 7H, 15H- [1,4] dioxino [2,3-a: 5,6-a '] dicarbazole was used as a reaction product. , 8.1 g of the target compound was obtained.

GC-Mass (calculated: 669.22 g / mol, measured: 669.74 g / mol)

[ Preparation Example  3]

1. c-1 ( 5H, 13H - [1,4] dioxino [2,3-b: 5,6-b '] dicarbazole ) Synthesis of

The procedure of Step 1 (a-1) in Preparation Example 1 and Step 2 (b) of Preparation Example 2 were repeated except that 2,7-dibromodibenzo [b, e] [1,4] b-2), 5.2 g of the desired compound was obtained.

GC-Mass (theory: 362.11 g / mol, measured: 362.39 g / mol)

2. c-2 (5 - ( [1,1'- biphenyl] -4-yl) - 5H, 13H - [1,4 ] dioxino [2,3-b: 5,6-b '] synthesis of dicarboxylic bar sol)

(Step a-3) of Preparation Example 1, except that 5H, 13H- [1,4] dioxino [2,3- b: 5,6-b '] dicarbazole was used as a reactant. Was carried out to obtain 5.9 g of the title compound.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

3. c-3 (7- (3- (4,6- diphenyl-1,3,5-triazin-2-yl) phenyl) - 7H, 15H - [1,4 ] dioxino [2, 3-a: 5,6-a '] dicarbazole)

(Step b-4) of Preparation Example 2, except that 5H, 13H- [1,4] dioxino [2,3- b: 5,6-b '] dicarbazole was used as a reactant. And 5 g of the target compound were obtained.

GC-Mass (calculated: 669.22 g / mol, measured: 669.74 g / mol)

[ Preparation Example  4]

1. d-1 ( 1H, 9H - [1,4] dithieno [2,3-c: 5,6-c '] dicarbazole ) Synthesis of

The procedure of Step 1 (a-1) and Step 2 (a-2) in Preparation Example 1 was repeated except that 1,6-dibromothianthrene was used as a reactant, to obtain the desired compound 7.6 g.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. d-2 (1 - ( [1,1'- biphenyl] -4-yl) - 1H, 9H - [1,4 ] dithiane ENO [2,3-c: 5,6-c '] dicarboxylic synthesis of bar sol)

3 (step a-3) of Preparation Example 1, except that 1H, 9H- [1,4] dithieno [2,3-c: 5,6- The same procedure was followed to obtain 5.2 g of the title compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

3. d-3 (1 - ( [1,1'- biphenyl] -3-yl) - 1H, 9H - [1,4 ] dithiane ENO [2,3-c: 5,6-c '] dicarboxylic synthesis of bar sol)

The procedure of Step 4 (a-4) of Preparation Example 1 was repeated except that 1H, 9H- [1,4] dithieno [2,3-c: 5,6-c '] dicarbazole was used as a reactant. The same procedure was followed to obtain 8.2 g of the target compound.

 GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

4. d-4 (1- (4,6- diphenyl-1,3,5-triazin-2-yl) - 1H, 9H - [1,4 ] dithiane Ino [2,3- c: 5, 6-c '] < / RTI > dicarbazole)

The procedure of Step 5 (a-5 preparation) of Preparation Example 1 was repeated except that 1H, 9H- [1,4] dithieno [2,3-c: 5,6- The same procedure was followed to obtain 7.1 g of the title compound.

 GC-Mass (calculated: 625.14 g / mol, measured: 625.77 g / mol)

[ Preparation Example  5]

1. e-1 ( 7H, 15H - [1,4] dithieno [2,3-a: 5,6-a '] dicarbazole ) Synthesis of

The procedure of Step 1 (b-1) and Step 2 (b-2) of Preparation Example 2 was repeated except that 1,6-dibromothianthrene was used as the reactant, g.

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. e-2 (7 - ( [1,1'- biphenyl] -4-yl) - 7H, 15H - [1,4 ] dithiane ENO [2,3-a: 5,6-a '] dicarboxylic synthesis of bar sol)

Except that 7H, 15H- [1,4] dithieno [2,3-a: 5,6-a '] dicarbazole was used as a reactant in Step 3 of Preparation Example 2 (step b-3) The same procedure was followed to obtain 7.4 g of the target compound.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

3. e-3 (7- (3- (4,6- diphenyl-1,3,5-triazin-2-yl) phenyl) - 7H, 15H - [1,4 ] ditiyi [2,3 -a: 5,6-a '] dicarbazole)

Except that 7H, 15H- [1,4] dithieno [2,3-a: 5,6-a '] dicarbazole was used as a reactant in Step 4 (b-4 production step) of Preparation Example 2 and The same procedure was followed to obtain 8.1 g of the title compound.

GC-Mass (calculated: 669.22 g / mol, measured: 669.74 g / mol)

[ Preparation Example  6]

1. f-1 ( 5H, 13H - [1,4] dithieno [2,3-b: 5,6-b '] dicarbazole ) Synthesis of

The procedure of Step 1 (c-1) of Preparation Example 3 was followed except that 2,7-dibromothianthrene was used as a reactant, to obtain 8.9 g of the desired compound.

GC-Mass (calculated: 934.92 g / mol, measured: 935.55 g / mol)

2. f-2 (5 - ( [1,1'- biphenyl] -4-yl) - 5H, 13H - [1,4 ] dithiane ENO [2,3-b: 5,6-b '] dicarboxylic synthesis of bar sol)

Except that 5H, 13H- [1,4] dithieno [2,3-b: 5,6-b '] dicarbazole was used as a reactant in step 2 (preparation step c-2) of Preparation Example 3 The same procedure was followed to obtain 5.9 g of the title compound.

GC-Mass (calculated: 546.17 g / mol, measured: 546.71 g / mol)

3. f-3 (5- (3- (4,6- diphenyl-1,3,5-triazin-2-yl) phenyl) - 5H, 13H - [1,4 ] ditiyi [2,3 -b: 5,6-b '] dicarbazole)

Except that 5H, 13H- [1,4] dithieno [2,3-b: 5,6-b '] dicarbazole was used as a reactant in step 3 (preparation step c-3) The same procedure was followed to obtain 5 g of the target compound.

GC-Mass (701.11 g / mol, measured: 701.87 g / mol)

[ Preparation Example  7]

1. Synthesis of g-1 (6,6,14,14- tetramethyl- 1,6,9,14 -tetrahydrobenzo [1,2-c: 4,5-c '] dicarbazole )

Step 1 (preparation step a-1) of Preparation Example 1 and step (b) of Preparation Example 1 were repeated except that 1,5-dibromo-9,9,10,10-tetramethyl-9,10-dihydroanthracene was used as a reactant. 2 (preparation step a-2), 7.6 g of the desired compound was obtained.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. g-2 (1 - ([1,1'-biphenyl] -4-yl) -6,6,14,14- tetramethyl- 1,6,9,14- tetrahydrobenzo [ 2-c: 4,5-c '] dicarbazole)

Preparation Example 1 was repeated except that 6,6,14,14-tetramethyl-1,6,9,14-tetrahydrobenzo [1,2-c: 4,5-c '] dicarbazole was used as a reactant. (Step a-3) to obtain 5.2 g of the title compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

3. g-3 (1 - ([1,1'-biphenyl] -3-yl) -6,6,14,14- tetramethyl- 1,6,9,14- tetrahydrobenzo [ 2-c: 4,5-c '] dicarbazole)

Preparation Example 1 was repeated except that 6,6,14,14-tetramethyl-1,6,9,14-tetrahydrobenzo [1,2-c: 4,5-c '] dicarbazole was used as a reactant. 4-one (step a-4), 8.2 g of the desired compound was obtained.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

4. g-4 (1- (4,6- diphenyl-1,3,5-triazin-2-yl) -6,6,14,14- tetramethyl-1,6,9,14- tetra Hydrobenzo [1,2-c: 4,5-c '] dicarbazole)

Preparation Example 1 was repeated except that 6,6,14,14-tetramethyl-1,6,9,14-tetrahydrobenzo [1,2-c: 4,5-c '] dicarbazole was used as a reactant. The title compound (7.1 g) was obtained by following the same procedure as in Step 5 (a-5).

GC-Mass (calculated: 625.14 g / mol, measured: 625.77 g / mol)

[ Preparation Example  8]

1. h-1 (1- (4,6- diphenyl-1,3,5-triazin-2-yl) -6,6,14,14- tetramethyl-1,6,9,14- tetra Hydrobenzo [1,2-c: 4,5-c '] dicarbazole)

Step 1 (preparation step b-1) of Preparation Example 2 and step (b-1) of Preparation Example 2 were repeated except that 1,5-dibromo-9,9,10,10-tetramethyl-9,10-dihydroanthracene was used as a reactant. 2 (preparation step b-2), 5.5 g of the desired compound was obtained.

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. Preparation of h-2 (7 - ([1,1'-biphenyl] -4-yl) -8,8,16,16- tetramethyl- 7,8,15,16- tetrahydrobenzo [ 2-a: 4,5-a '] dicarbazole)

Except that 8,8,16,16-tetramethyl-7,8,15,16-tetrahydrobenzo [1,2-a: 4,5-a '] dicarbazole was used as a reactant. (B-3) of Step 3, to obtain 7.4 g of the desired compound.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

3. h-3 (7- (3- (4,6- diphenyl-1,3,5-triazin-2-yl) phenyl) -8,8,16,16- tetramethyl-7,8, 15,16-tetrahydrobenzo [1,2-a: 4,5-a '] dicabazole)

Except that 8,8,16,16-tetramethyl-7,8,15,16-tetrahydrobenzo [1,2-a: 4,5-a '] dicarbazole was used as a reactant. (B-4) of Step 4 (b-4), 8.1 g of the title compound was obtained.

GC-Mass (calculated: 669.22 g / mol, measured: 669.74 g / mol)

[ Preparation Example  9]

1. Synthesis of i-1 (7,7,15,15- tetramethyl- 5,7,13,15 -tetrahydrobenzo [1,2-b: 4,5-b '] dicabazole )

The same procedure as in the step 1 (preparation step c-1) of Preparation Example 3 was carried out except that 2,6-dibromo-9,9,10,10-tetramethyl-9,10-dihydroanthracene was used as a reactant. Was carried out to obtain 8.9 g of the desired compound.

GC-Mass (calculated: 934.92 g / mol, measured: 935.55 g / mol)

2. Synthesis of i-2 (5 - ([1,1'-biphenyl] -4-yl) -7,7,15,15- tetramethyl- 5,7,13,15- tetrahydrobenzo [ 2-b: 4,5-b '] dicarbazole)

Except that 7,7,15,15-tetramethyl-5,7,13,15-tetrahydrobenzo [1,2-b: 4,5-b '] dicarbazole was used as a reaction product. (Step c-2), the title compound (5.9 g) was obtained.

GC-Mass (calculated: 546.17 g / mol, measured: 546.71 g / mol)

3. i-3 (5- (3- (4,6- diphenyl-1,3,5-triazin-2-yl) phenyl) -7,7,15,15- tetramethyl-5,7, Synthesis of 13,15-tetrahydrobenzo [1,2-b: 4,5-b '] dicarbazole)

Except that 7,7,15,15-tetramethyl-5,7,13,15-tetrahydrobenzo [1,2-b: 4,5-b '] dicarbazole was used as a reaction product. (C-3), to obtain 5 g of the target compound.

GC-Mass (701.11 g / mol, measured: 701.87 g / mol)

[ Preparation Example  10]

1. Synthesis of j-1 (6,14-dimethyl-6,14-diphenyl-1,6,9,14 -tetrahydrobenzo [1,2-c: 4,5- c '] dicarbazole)

Step 1 (preparation step a-1) of Preparation Example 1 was repeated except that 1,5-dibromo-9,10-dimethyl-9,10-diphenyl-9,10-dihydroanthracene was used as a reactant. And the step 2 (a-2 preparation step), 7.6 g of the desired compound was obtained.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. j-2 (1 - ( [1,1'- biphenyl] -4-yl) -6,14- dimethyl -6,14- diphenyl -1,6,9,14- tetrahydro Jethro and benzo [ 1,2-c: 4,5-c '] dicarbazole)

Except that 6,14-dimethyl-6,14-diphenyl-1,6,9,14-tetrahydrobenzo [1,2-c: 4,5-c '] dicarbazole was used as a reactant. The procedure of Step 3 (a-3) of Example 1 was repeated to obtain 5.2 g of the target compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

3. j-3 (1 - ([1,1'-biphenyl] -3-yl) -6,14-dimethyl- 6,14-diphenyl-1,6,9,14- tetrahydrobenzo [ 1,2-c: 4,5-c '] dicarbazole)

Except that 6,14-dimethyl-6,14-diphenyl-1,6,9,14-tetrahydrobenzo [1,2-c: 4,5-c '] dicarbazole was used as a reactant. The procedure of Step 4 of Example 1 (a-4) was followed to obtain 8.2 g of the target compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

4. j-4 (1- (4,6-Diphenyl-1,3,5-triazin-2-yl) -6,14-dimethyl-6,14-diphenyl- -Tetrahydrobenzo [1,2-c: 4,5-c '] dicarbazole)

Except that 6,14-dimethyl-6,14-diphenyl-1,6,9,14-tetrahydrobenzo [1,2-c: 4,5-c '] dicarbazole was used as a reactant. The procedure of Step 5 of Example 1 (a-5) was repeated to obtain 7.1 g of the desired compound.

 GC-Mass (calculated: 625.14 g / mol, measured: 625.77 g / mol)

[ Preparation Example  11]

1. Synthesis of k-1 (8,16-dimethyl-8,16-diphenyl-7,8,15,16 -tetrahydrobenzo [1,2-a: 4,5- a '] dicabazole )

Step 1 (preparation step b-1) of Preparation Example 2 was repeated except that 1,5-dibromo-9,10-dimethyl-9,10-diphenyl-9,10-dihydroanthracene was used as a reactant. And the step 2 (b-2) were repeated to obtain the title compound (5.5 g).

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. Preparation of k-2 (7 - ([1,1'-biphenyl] -4-yl) -8,16-dimethyl-8,16-diphenyl-7,8,15,16- tetrahydrobenzo [ , 2-a: 4,5-a '] dicarbazole)

Except that 8,16-dimethyl-8,16-diphenyl-7,8,15,16-tetrahydrobenzo [1,2-a: 4,5-a '] dicarbazole was used as a reactant. The procedure of Step 3 (b-3) of Example 2 was repeated to obtain 7.4 g of the target compound.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

3. k-3 (7- (3- (4,6- diphenyl-1,3,5-triazin-2-yl) phenyl) -8,8,16,16- tetramethyl-7,8, 15,16-tetrahydrobenzo [1,2-a: 4,5-a '] dicabazole)

Except that 8,16-dimethyl-8,16-diphenyl-7,8,15,16-tetrahydrobenzo [1,2-a: 4,5-a '] dicarbazole was used as a reactant. The same procedure as in step 4 (b-4) of Example 2 was carried out to obtain 8.1 g of the target compound.

GC-Mass (calculated: 669.22 g / mol, measured: 669.74 g / mol)

[ Preparation Example  12]

Synthesis of l-1 (7,15-dimethyl-7,15-diphenyl-5,7,13,15 -tetrahydrobenzo [1,2-b: 4,5- b '] dicabazole )

Step 1 (Preparation step c-1) of Preparation Example 3 was repeated except that 2,6-dibromo-9,10-dimethyl-9,10-diphenyl-9,10-dihydroanthracene was used as a reactant. The target compound (8.9 g) was obtained.

GC-Mass (calculated: 934.92 g / mol, measured: 935.55 g / mol)

2. Synthesis of l-2 (5 - ([1,1'-biphenyl] -4-yl) -7,15-dimethyl-7,15-diphenyl-5,7,13,15- tetrahydrobenzo [ , 2-b: 4,5-b '] dicarbazole)

Except that 7,15-dimethyl-7,15-diphenyl-5,7,13,15-tetrahydrobenzo [1,2-b: 4,5-b '] dicarbazole was used as a reactant. The procedure of Step 2 of Example 3 (c-2) was carried out to obtain 5.9 g of the title compound.

GC-Mass (calculated: 546.17 g / mol, measured: 546.71 g / mol)

3. Preparation of l- 3 (5- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -7,15- Synthesis of 7,13,15-tetrahydrobenzo [1,2-b: 4,5-b '] dicarbazole)

Except that 7,15-dimethyl-7,15-diphenyl-5,7,13,15-tetrahydrobenzo [1,2-b: 4,5-b '] dicarbazole was used as a reactant. The same procedure as in step 3 of Example 3 (c-3) was conducted to obtain 5 g of the target compound.

GC-Mass (701.11 g / mol, measured: 701.87 g / mol)

[ Preparation Example  13]

1. m-1 (6,14- diphenyl -1,6,9,14- tetrahydro-indol-di [3,2-a: 3 ', 2'-h] phenazine) Synthesis of

1 (preparation step a-1) and step 2 (a) of Preparation Example 1 were repeated except that 1,6-dibromo-5,10-diphenyl-5,10-dihydrophenazine was used as a reactant. -2 < / RTI > production step), 7.6 g of the desired compound was obtained.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. Preparation of m-2 (1 - ([1,1'-biphenyl] -4-yl) -6,14-diphenyl-1,6,9,14- tetrahydrodiindolo [3,2-a : Synthesis of 3 ', 2'-h] phenazine

The procedure of Preparation Example 1 was repeated except that 6,14-diphenyl-1,6,9,14-tetrahydrodiindolo [3,2-a: 3 ', 2'-h] The same procedure as in step 3 (a-3) was carried out to obtain 5.2 g of the target compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

3. Synthesis of m-3 (1 - ([1,1'-biphenyl] -3-yl) -6,14-diphenyl-1,6,9,14- tetrahydrodiindolo [3,2-a : 3 ', 2'-h] phenazine)

The procedure of Preparation Example 1 was repeated except that 6,14-diphenyl-1,6,9,14-tetrahydrodiindolo [3,2-a: 3 ', 2'-h] The same procedure as in Step 4 (a-4) was carried out to obtain 8.2 g of the desired compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

4. Synthesis of m-4 (1- (4,6-diphenyl-1,3,5-triazin-2-yl) -6,14-diphenyl-1,6,9,14- tetrahydroindole Synthesis of [3,2-a: 3 ', 2'-h] phenazine)

The procedure of Preparation Example 1 was repeated except that 6,14-diphenyl-1,6,9,14-tetrahydrodiindolo [3,2-a: 3 ', 2'-h] The same procedure as in step 5 (a-5) was carried out to obtain 7.1 g of the title compound.

GC-Mass (calculated: 625.14 g / mol, measured: 625.77 g / mol)

[ Preparation Example  14]

1. n-1 (8,16- diphenyl -7,8,15,16- tetrahydro-indol-di [2,3-a: 2 ', 3'-h] phenazine) Synthesis of

Step 1 (preparation step b-1) and step 2 (b) of Preparation Example 2 were repeated except that 1,6-dibromo-5,10-diphenyl-5,10-dihydrophenazine was used as a reactant. -2 < / RTI > production step), 5.5 g of the desired compound was obtained.

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. Synthesis of n-2 (7 - ([1,1'-biphenyl] -4-yl) -8,16-diphenyl-7,8,15,16- tetrahydrodiindolo [2,3- a : 2 ', 3'-h] phenazine)

The procedure of Preparation Example 2 was repeated except that 8,16-diphenyl-7,8,15,16-tetrahydrodiindolo [2,3-a: 2 ', 3'-h] The same procedure as in Step 3 (b-3) was carried out to obtain 7.4 g of the desired compound.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

3. n-3 (7- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -8,16- Synthesis of tetrahydrodiindolo [2,3-a: 2 ', 3'-h] phenazine)

The procedure of Preparation Example 2 was repeated except that 8,16-diphenyl-7,8,15,16-tetrahydrodiindolo [2,3-a: 2 ', 3'-h] The same procedure as in step 4 (b-4) was carried out to obtain the desired compound (8.1 g).

GC-Mass (calculated: 669.22 g / mol, measured: 669.74 g / mol)

[ Preparation Example  15]

1. o-1 (7,15- diphenyl -5,7,13,15- tetrahydro-indol-di [2,3-b: 2 ', 3'-i] phenazine) Synthesis of

The same procedure as in step 1 (c-1) of Preparation Example 3 was carried out except that 2,7-dibromo-5,10-diphenyl-5,10-dihydrophenazine was used as a reactant To obtain 8.9 g of the desired compound.

GC-Mass (calculated: 934.92 g / mol, measured: 935.55 g / mol)

2. Synthesis of o- 2 (5 - ([1,1'-biphenyl] -4-yl) -7,15-diphenyl-5,7,13,15- tetrahydrodiindolo [2,3- b : 2 ', 3'-i] phenazine)

The procedure of Preparation Example 3 was repeated except that 7,15-diphenyl-5,7,13,15-tetrahydrodiindolo [2,3-b: 2 ', 3'-i] The same procedure as in Step 2 (c-2) was carried out to obtain 5.9 g of the title compound.

GC-Mass (calculated: 546.17 g / mol, measured: 546.71 g / mol)

3. Preparation of o- 3 (5- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -7,15- Synthesis of tetrahydrodiindolo [2,3-b: 2 ', 3'-i] phenazine)

The procedure of Preparation Example 3 was repeated except that 7,15-diphenyl-5,7,13,15-tetrahydrodiindolo [2,3-b: 2 ', 3'-i] The same procedure as in Step 3 (c-3) was carried out to obtain 5 g of the target compound.

GC-Mass (701.11 g / mol, measured: 701.87 g / mol)

[ Preparation Example  16]

Synthesis of p-1 (14,14-dimethyl-9,14 -dihydro- 1H -pyrano [2,3-c: 5,6-c '] dicarbazole )

The procedure of Step 1 (a) of Preparation Example 1 was repeated except that 14,14-dimethyl-9,14-dihydro-1H-pyrano [2,3-c: 5,6- -1 production step) and step 2 (a-2 production step), the objective compound (7.6 g) was obtained.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. p-2 (9 - ( [1,1'- biphenyl] -4-yl) -14,14- dimethyl -9,14- dihydro -1H- pyrazol-no [2,3-c: 5, 6-c '] < / RTI > dicarbazole)

Step 3 (a) of Preparation Example 1 was repeated except that 14,14-dimethyl-9,14-dihydro-1H-pyrano [2,3-c: 5,6- -3 < / RTI > production step), 5.2 g of the desired compound was obtained.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

3. p-3 (9 - ( [1,1'- biphenyl] -3-yl) -14,14- dimethyl -9,14- dihydro -1H- pyrazol-no [2,3-c: 5, 6-c '] < / RTI > dicarbazole)

The procedure of Step 4 (a) of Preparation Example 1 was repeated except that 14,14-dimethyl-9,14-dihydro-1H-pyrano [2,3-c: 5,6- -4 < / RTI > production step), 8.2 g of the desired compound was obtained.

 GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

[ Preparation Example  17]

1. Synthesis of q-1 (16,16-dimethyl-15,16 -dihydro- 7H -pyrano [2,3-a: 5,6-a '] dicarbazole )

(Step b-1) and step 2 (step b-2) of Preparation Example 2 were repeated except that 1,5-dibromo-9,9-dimethyl-9H- And the target compound (5.5 g) was obtained.

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. q-2 (7 - ( [1,1'- biphenyl] -4-yl) -16,16- dimethyl -15,16- dihydro -7H- pyrazol-no [2,3-a: 5, 6-a '] dicarbazole)

Except that 16,16-dimethyl-15,16-dihydro-7H-pyrano [2,3-a: 5,6-a '] dicarbazole was used as a reaction product. -3 < / RTI > production step), 7.4 g of the desired compound was obtained.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

3. q-3 (7- (3- (4,6-Diphenyl-1,3,5-triazin-2-yl) phenyl) -16,16-dimethyl-15,16 - dihydro- Pyrano [2,3-a: 5,6-a '] dicarbazole)

Step 4 (b) of Preparation Example 2 was repeated except that 16,16-dimethyl-15,16-dihydro-7H-pyrano [2,3-a: 5,6-a '] dicarbazole was used as a reactant. -4 < / RTI > production step), 8.1 g of the desired compound was obtained.

GC-Mass (calculated: 669.22 g / mol, measured: 669.74 g / mol)

[ Preparation Example  18]

1. Synthesis of r-1 (15,15-dimethyl-13,15 -dihydro- 5H -pyrano [2,3-b: 5,6-b '] dicabazole )

The procedure of Step 1 (c-1) in Preparation Example 3 was repeated except that 2,6-dibromo-9,9-dimethyl-9H-xanthene was used as a reactant, to obtain 8.9 g ≪ / RTI >

GC-Mass (calculated: 934.92 g / mol, measured: 935.55 g / mol)

2. r-2 (13 - ( [1,1'- biphenyl] -4-yl) -15,15- dimethyl -13,15- dihydro -5H- pyrazol-no [2,3-b: 5, 6-b '] dicarbazole)

Step 2 (c) of Preparation Example 3 was repeated except that 15,15-dimethyl-13,15-dihydro-5H-pyrano [2,3- b: 5,6-b '] dicarbazole was used as a reaction product. -2 < / RTI > production step), 5.9 g of the desired compound was obtained.

GC-Mass (calculated: 546.17 g / mol, measured: 546.71 g / mol)

3. Preparation of r-3 (5- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -15,15-dimethyl-13,15 - dihydro- Pyrano [2,3-b: 5,6-b '] dicarbazole)

Except that 15, 15-dimethyl-13,15-dihydro-5H-pyrano [2,3-b: 5,6-b '] dicarbazole was used as a reaction product. -3 < / RTI > production step), 5 g of the desired compound was obtained.

GC-Mass (701.11 g / mol, measured: 701.87 g / mol)

[ Preparation Example  19]

1. Synthesis of s-1 (14- methyl -14 - phenyl-9,14 -dihydro- 1H -pyrano [2,3-c: 5,6-c '] dicabazole )

(Step a-1) and step 2 (step a-2) of Preparation Example 1 were repeated except that 1,5-dibromo-9-methyl-9- Step 7.6g of the target compound was obtained.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. s-2 (9 - ( [1,1'- biphenyl] -4-yl) 14-methyl-14-phenyl -9,14- dihydro -1H- pyrazol-no [2,3-c: 5,6-c '] dicarbazole)

Step 3 of Preparation Example 1 was repeated except that 14-methyl-14-phenyl-9,14-dihydro-1H-pyrano [2,3-c: 5,6- (preparation step a-3), 5.2 g of the desired compound was obtained.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

[ Preparation Example  20]

1. Synthesis of t-1 (16- methyl- 16-phenyl-15,16 -dihydro- 7H -pyrano [2,3-a: 5,6-a '] dicarbazole )

Step 1 (preparation step b-1) and step 2 (preparation of b-2) of Preparation Example 2 were repeated except that 1,5-dibromo-9-methyl- Step 5) was repeated to give the desired compound (5.5 g).

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. t-2 (7 - ( [1,1'- biphenyl] 4-yl) methyl -16- -16- phenyl -15,16- dihydro -7H- pyrazol-no [2,3-a: 5,6-a '] dicarbazole)

Except that 16-methyl-16-phenyl-15,16-dihydro-7H-pyrano [2,3-a: 5,6-a '] dicarbazole was used as a reaction product. (b-3), 7.4 g of the desired compound was obtained.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

[ Preparation Example  21]

1. Synthesis of u-1 (14- methyl -14 - phenyl-9,14 -dihydro- 1H -thiopyrano [2,3-c: 5,6-c '] dicabazole )

(A-1) and (a-2) of Preparation Example 1 were repeated except that 1,5-dibromo-9-methyl-9- The same procedure as in the preparation step) was carried out to obtain 7.6 g of the desired compound.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. u-2 (9 - ( [1,1'- biphenyl] -4-yl) 14-methyl-14-phenyl -9,14- dihydro -1H- tea operational pyrano [2,3-c : 5,6-c '] dicarbazole)

The procedure of Preparation Example 1 was repeated except that 14-methyl-14-phenyl-9,14-dihydro-1H-thiopyrano [2,3-c: 5,6- 3 (preparation step a-3), 5.2 g of the desired compound was obtained.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

[ Preparation Example  22]

1. Synthesis of v-1 (16- methyl- 16-phenyl-15,16 -dihydro- 7H -thiopyrano [2,3-a: 5,6-a '] dicabazole )

(Step b-1) and step 2 (b-2) of Preparation Example 2 were repeated except that 1,5-dibromo-9-methyl- The same procedure as in the preparation step) was carried out to obtain the desired compound (5.5 g).

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. v-2 (7 - ( [1,1'- biphenyl] -4-yl) methyl -16- -16- phenyl -15,16- dihydro -7H- thio-pyrano [2,3-a : 5,6-a '] dicarbazole)

Except that 16-methyl-16-phenyl-15,16-dihydro-7H-thiopyrano [2,3-a: 5,6-a '] dicarbazole was used as a reaction product. 3 (preparation step b-3), 7.4 g of the desired compound was obtained.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

[ Preparation Example  23]

1. Synthesis of w-1 (14,14-dimethyl-6-phenyl-1,6,9,14 -tetrahydrodiindolo [3,2-a: 3 ', 2'- h] acridine)

Step 1 (preparation step a-1) of Preparation Example 1 and preparation of the compound of Preparation Example 1 were repeated except for using 1,5-dibromo-9,9-dimethyl-10-phenyl-9,10-dihydro- The same procedure as in Step 2 (a-2) was carried out to obtain 7.6 g of the desired compound.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. Synthesis of w-2 (9 - ([1,1'-biphenyl] -4-yl) -14,14-dimethyl-6-phenyl-1,6,9,14- tetrahydroindiolo [ 2-a: 3 ', 2'-h] acridine)

Except that 14,14-dimethyl-6-phenyl-1,6,9,14-tetrahydrodiindolo [3,2-a: 3 ', 2'-h] acridine was used as a reactant. The procedure of Step 3 of Preparation Example 1 (step a-3) was repeated to obtain 5.2 g of the target compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

3. Synthesis of w-3 (9 - ([1,1'-biphenyl] -3-yl) -14,14-dimethyl-6-phenyl-1,6,9,14- tetrahydroindiolo [ 2-a: 3 ', 2'-h] acridine)

Except that 14,14-dimethyl-6-phenyl-1,6,9,14-tetrahydrodiindolo [3,2-a: 3 ', 2'-h] acridine was used as a reactant. The procedure of Step 4 of Preparation Example 1 (step a-4) was repeated to obtain 8.2 g of the target compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

[ Preparation Example  24]

1. Synthesis of x-1 (16,16-dimethyl-8-phenyl-7,8,15,16 -tetrahydrodiindolo [2,3- a: 2 ', 3'-h] acridine)

Step 1 (preparation step b-1) of Preparation Example 2 was repeated except that 1,5-dibromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine was used as a reactant. The same procedure as in Step 2 (b-2) was carried out to obtain the desired compound (5.5 g).

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. Preparation of x-2 (7 - ([1,1'-biphenyl] -4-yl) -16,16-dimethyl-8-phenyl-7,8,15,16- tetrahyd ro diindolo [ , 3-a: 2 ', 3'-h] acridine)

Except that 16,16-dimethyl-8-phenyl-7,8,15,16-tetrahydrodiindolo [2,3-a: 2 ', 3'-h] acridine was used as a reactant. The procedure of Step 3 of Preparation Example 2 (step b-3) was repeated to obtain the desired compound (7.4 g).

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

3. Preparation of x-3 (7- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -16,16-dimethyl- , 16-tetrahydrodiindolo [2,3-a: 2 ', 3'-h] acridine)

Except that 16,16-dimethyl-8-phenyl-7,8,15,16-tetrahydrodiindolo [2,3-a: 2 ', 3'-h] acridine was used as a reactant. The procedure of Step 4 of Preparation Example 2 (step b-4) was repeated to obtain the desired compound (8.1 g).

GC-Mass (calculated: 669.22 g / mol, measured: 669.74 g / mol)

[ Preparation Example  25]

1. Synthesis of y-1 (15,15-dimethyl-7-phenyl-5,7,13,15 -tetrahydrodiindolo [2,3- b: 2 ', 3'-i] acridine)

Step 1 (preparation step c-1) of Preparation Example 3 was repeated except that 2,6-dibromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine was used as a reactant. The same procedure was followed to obtain the desired compound (8.9 g).

GC-Mass (calculated: 934.92 g / mol, measured: 935.55 g / mol)

2. Synthesis of y-2 (13 - ([1,1'-biphenyl] -4-yl) -15,15-dimethyl-7-phenyl-5,7,13,15- tetrahydropyrido [ , 3-b: 2 ', 3'-i] acridine)

Except that 15,15-dimethyl-7-phenyl-5,7,13,15-tetrahydrodiindolo [2,3-b: 2 ', 3'-i] acridine was used as a reactant. The procedure of Step 2 of Preparation Example 3 (c-2 production step) was carried out to obtain the desired compound (5.9 g).

GC-Mass (calculated: 546.17 g / mol, measured: 546.71 g / mol)

3. y-3 (5- (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) -15,15-dimethyl- , 15-tetrahydrodiindolo [2,3-b: 2 ', 3'-i] acridine

The reaction was carried out using 13 - ([1,1'-biphenyl] -4-yl) -15,15-dimethyl-7-phenyl-5,7,13,15- tetrahydrodiindolo [2,3- 2 ', 3'-i] acridine was used in place of 3-iodo-4-methylpyridine in step 3 of Preparation Example 3 (step c-3).

GC-Mass (701.11 g / mol, measured: 701.87 g / mol)

[ Preparation Example  26]

1. Synthesis of z-1 (14- methyl- 6,14-diphenyl-1,6,9,14 -tetrahydrodiindolo [3,2-a: 3 ', 2'- h] synthesis

Step 1 (preparation step a-1) of Preparation Example 1 was repeated except that 1,5-dibromo-9-methyl-9,10-diphenyl-9,10-dihydroacridine was used as a reactant. And the step 2 (a-2 preparation step), 7.6 g of the desired compound was obtained.

GC-Mass (theory: 394.06 g / mol, measured: 394.51 g / mol)

2. z-2 (9 - ([1,1'-biphenyl] -4-yl) -14- methyl- 6,14-diphenyl-1,6,9,14- tetrahydroindiolo [ , 2-a: 3 ', 2'-h] acridine)

Except that 14-methyl-6,14-diphenyl-1,6,9,14-tetrahydrodiindolo [3,2-a: 3 ', 2'-h] acridine was used as a reactant The same procedure as in Step 3 (a-3) of Preparation Example 1 was conducted to obtain 5.2 g of the target compound.

GC-Mass (calculated: 546.14 g / mol, measured: 546.71 g / mol)

[ Preparation Example  27]

1. Synthesis of aa-1 (16- methyl- 8,16-diphenyl-7,8,15,16 -tetrahydrodiindolo [2,3- a: 2 ', 3'-h] synthesis

Step 1 (preparation step b-1) of Preparation Example 2 was repeated except that 1,5-dibromo-9-methyl-9,10-diphenyl-9,10-dihydroacridine was used as a reactant. And the step 2 (b-2) were repeated to obtain the title compound (5.5 g).

GC-Mass (calculated: 394.09 g / mol, measured: 394.51 g / mol)

2. Preparation of aa-2 (7 - ([1,1'-biphenyl] -4-yl) -16- methyl- 8,16-diphenyl-7,8,15,16- tetrahydroindolo [2 , 3-a: 2 ', 3'-h] acridine)

Except that 16-methyl-8,16-diphenyl-7,8,15,16-tetrahydrodiindolo [2,3-a: 2 ', 3'-h] acridine was used as a reactant The procedure of Step 3 of Preparation Example 2 (step b-3) was repeated to obtain 7.4 g of the target compound.

GC-Mass (theory: 514.17 g / mol, measurement: 514.58 g / mol)

[ Synthetic example  1] Synthesis of Mat 1

250 mL of xylene was added to 10 g (27.6 mmol) of 1H, 9H- [1,4] dioxino [2,3-c: 5,6-c '] dicarbazole and 12.39 g (60.77 mmol) of iodobenzene . 1.6 g (1.8 mmol) of Pd ₂ (dba) ₃ , 1.73 g (3.64 mmol) of Xphos and 29 g (303.8 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 (12.4 g, yield: 88%).

^{1 H-NMR: δ 11.2,} 7.88 (d, 3H), 7.79 ~ 7.67 (m, 17H), 7.52 (m, 4H), 6.83 (m, 2H);

HRMS [M] < ⁺ & gt ^; : 514.17

[ Synthetic example  2] Synthesis of Mat 2

The procedure of Synthesis Example 1 was repeated except that 4-bromo-1,1'-biphenyl was used as a reactant, to thereby yield 8.4 g of the target compound.

HRMS [M] < + >: 666.23

[ Synthetic example  3] Synthesis of Mat 3

The procedure of Synthesis Example 1 was repeated except that 3-bromo-1,1'-biphenyl was used as a reactant, to thereby yield 8 g of the target compound.

HRMS [M] < + >: 666.23

[ Synthetic example  4] Synthesis of Mat 4

The procedure of Synthesis Example 1 was repeated except for using 5'-bromo-1,1 ': 3', 1 "-terphenyl as a reactant, and 9.0 g of the target compound was obtained.

HRMS [M] < + >: 818.29

[ Synthetic example  5] Synthesis of Mat 5

The procedure of Synthesis Example 1 was repeated except that 2-bromodibenzo [b, d] furan was used as a reactant, to obtain 7.6 g of the title compound.

HRMS [M] < + >: 694.19

[ Synthetic example  6] Synthesis of Mat 6

The procedure of Synthesis Example 1 was repeated except that 3-bromo-9,9-dimethyl-9H-fluorene was used as a reactant, to obtain 5.4 g of the title compound.

HRMS [M] < + >: 746.29

[ Synthetic example  7] Synthesis of Mat 7

The procedure of Synthesis Example 1 was repeated except that 3-bromo-9-phenyl-9H-carbazole was used as a reactant, to thereby yield the desired compound (8.3 g).

HRMS [M] < + >: 844.28

[ Synthetic example  8] Synthesis of Mat 8

The procedure of Synthesis Example 1 was repeated except for using 9- (3-bromophenyl) -9H-carbazole as a reactant to obtain 8.1 g of the desired compound.

HRMS [M] < + >: 844.28

[ Synthetic example  9] Synthesis of Mat 9

The procedure of Synthesis Example 1 was repeated except that 4-bromodibenzo [b, d] thiophene was used as a reactant, to obtain 7.6 g of the title compound.

HRMS [M] < + >: 726.14

[ Synthetic example  10] Synthesis of Mat 10

The procedure of Synthesis Example 1 was repeated, except that 9- (3-bromophenyl) phenanthrene was used as a reactant to obtain 7 g of the desired compound.

HRMS [M] < + >: 866.29

[ Synthetic example  11] Synthesis of Mat 11

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 6.9 g of the title compound.

HRMS [M] < + >: 824.26

[ Synthetic example  12] Synthesis of Mat 12

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 10.5 g of the target compound.

HRMS [M] < + >: 976.33

[ Synthetic example  13] Synthesis of Mat 13

The procedure of Synthesis Example 3 was repeated except for using the compound a-3 obtained in Preparation Example 1 as a reactant, to obtain the object compound 5.5 g.

HRMS [M] < + >: 666.23

[ Synthetic example  14] Synthesis of Mat 14

The procedure of Synthesis Example 5 was repeated except for using the compound a-3 obtained in Preparation Example 1 as a reactant, to obtain 5.9 g of the title compound.

HRMS [M] < + >: 680.21

[ Synthetic example  15] Synthesis of Mat 15

The procedure of Synthesis Example 11 was repeated except for using the compound a-3 obtained in Preparation Example 1 as a reactant, to obtain 6.6 g of the title compound.

HRMS [M] < + >: 745.25

[ Synthetic example  16] Synthesis of Mat 16

The procedure of Synthesis Example 3 was repeated except for using the compound a-4 obtained in Preparation Example 1 as a reactant, to obtain 6.4 g of the target compound.

HRMS [M] < + >: 821.28

[ Synthetic example  17] Synthesis of Mat 17

The procedure of Synthesis Example 12 was repeated except for using the compound a-5 obtained in Preparation Example 1 as a reactant, to obtain 9.8 g of the title compound.

HRMS [M] < + >: 900.30

[ Synthetic example  18] Synthesis of Mat 18

The procedure of Synthesis Example 2 was repeated except for using the compound b-2 obtained in Preparation Example 2 as a reactant, to obtain 5.3 g of the target compound.

HRMS [M] < + >: 666.23

[ Synthetic example  19] Synthesis of Mat 19

The procedure of Synthesis Example 5 was repeated except for using the compound b-2 obtained in Preparation Example 2 as a reactant, to obtain 4.7 g of the title compound.

HRMS [M] < + >: 694.19

[ Synthetic example  20] Synthesis of Mat 20

The procedure of Synthesis Example 9 was repeated except for using the compound b-2 obtained in Preparation Example 2 as a reactant, to obtain 5.6 g of the title compound.

HRMS [M] < + >: 726.14

[ Synthetic example  21] Synthesis of Mat 21

The procedure of Synthesis Example 13 was repeated except for using the compound b-3 obtained in Preparation Example 2 as a reactant, to obtain 7.4 g of the objective compound.

HRMS [M] < + >: 666.23

[ Synthetic example  22] Synthesis of Mat 22

The procedure of Synthesis Example 3 was repeated except for using the compound b-4 obtained in Preparation Example 2 as a reactant, to obtain 6.7 g of the title compound.

HRMS [M] < + >: 821.28

[ Synthetic example  23] Synthesis of Mat 23

The procedure of Synthesis Example 5 was repeated except for using the compound b-4 obtained in Preparation Example 2 as a reactant, to obtain 7.9 g of the title compound.

HRMS [M] < + >: 835.26

[ Synthetic example  24] Synthesis of Mat 24

The procedure of Synthesis Example 2 was repeated except for using the compound c-1 obtained in Preparation Example 3 as a reactant, to obtain 4.8 g of the title compound.

HRMS [M] < + >: 666.23

[ Synthetic example  25] Synthesis of Mat 25

The procedure of Synthesis Example 5 was repeated except for using the compound c-1 obtained in Preparation Example 3 as a reactant, to obtain 7.1 g of the title compound.

HRMS [M] < + >: 694.19

[ Synthetic example  26] Synthesis of Mat 26

The procedure of Synthesis Example 9 was repeated except for using the compound c-1 obtained in Preparation Example 3 as a reactant, to obtain 8.8 g of the title compound.

HRMS [M] < + >: 726.14

[ Synthetic example  27] Synthesis of Mat 27

The procedure of Synthesis Example 3 was repeated except for using the compound c-2 obtained in Preparation Example 3 as a reactant, to obtain 5.3 g of the target compound.

HRMS [M] < + >: 666.23

[ Synthetic example  28] Synthesis of Mat 28

The procedure of Synthesis Example 3 was repeated except for using the compound c-3 obtained in Preparation Example 3 as a reactant, to obtain 7.8 g of the title compound.

HRMS [M] < + >: 821.28

[ Synthetic example  29] Synthesis of Mat 29

The procedure of Synthesis Example 5 was repeated except for using the compound c-3 obtained in Preparation Example 3 as a reactant, to obtain 9.1 g of the title compound.

HRMS [M] < + >: 835.26

[ Synthetic example  30] Synthesis of Mat 30

The procedure of Synthesis Example 1 was repeated except for using the d-1 compound obtained in Preparation Example 4 as a reactant, to obtain 4.4 g of the desired compound.

HRMS [M] < + >: 546.14

[ Synthetic example  31] Synthesis of Mat 31

The procedure of Synthesis Example 2 was repeated except for using the d-1 compound obtained in Preparation Example 4 as a reactant, to obtain 5.9 g of the title compound.

HRMS [M] < + >: 698.19

[ Synthetic example  32] Synthesis of Mat 32

The procedure of Synthesis Example 3 was repeated except for using the d-1 compound obtained in Preparation Example 4 as a reactant, to obtain 6.6 g of the title compound.

HRMS [M] < + >: 698.19

[ Synthetic example  33] Synthesis of Mat 33

The procedure of Synthesis Example 4 was repeated except for using the compound d-1 obtained in Preparation Example 4 as a reactant, to obtain 6.1 g of the title compound.

HRMS [M] < + >: 850.25

[ Synthetic example  34] Synthesis of Mat 34

The procedure of Synthesis Example 5 was repeated except that Preparation Example 4 and d-1 were used as reactants, to obtain 8.3 g of the title compound. HRMS [M] < + >: 726.14

[ Synthetic example  35] Synthesis of Mat 35

The procedure of Synthesis Example 6 was repeated except for using the compound d-1 obtained in Preparation Example 4 as a reactant to obtain 8.2 g of the target compound.

HRMS [M] < + >: 778.25

[ Synthetic example  36] Synthesis of Mat 36

The procedure of Synthesis Example 7 was repeated except for using the compound d-1 obtained in Preparation Example 4 as a reactant, to obtain the desired compound 7.6 g.

HRMS [M] < + >: 876.24

[ Synthetic example  37] Synthesis of Mat 37

The procedure of Synthesis Example 8 was repeated except for using the compound d-1 obtained in Preparation Example 4 as a reactant, to obtain 5.7 g of the title compound.

HRMS [M] < + >: 876.24

[ Synthetic example  38] Synthesis of Mat 38

The procedure of Synthesis Example 9 was repeated except for using the compound d-1 obtained in Preparation Example 4 as a reactant, to obtain 6.9 g of the title compound.

HRMS [M] < + >: 758.10

[ Synthetic example  39] Synthesis of Mat 39

The procedure of Synthesis Example 10 was repeated except that d-1 compound obtained in Preparation Example 4 was used as a reactant, to obtain 7.5 g of the target compound.

HRMS [M] < + >: 898.25

[ Synthetic example  40] Mat40  synthesis

The procedure of Synthesis Example 11 was repeated except for using the compound d-1 obtained in Preparation Example 4 as a reactant, to obtain 5.2 g of the target compound.

HRMS [M] < + >: 856.22

[ Synthetic example  41] Synthesis of Mat 41

The procedure of Synthesis Example 12 was repeated, except that d-1 compound obtained in Preparation Example 4 was used as a reactant, to obtain 12 g of the title compound.

HRMS [M] < + >: 1008.28

[ Synthetic example  42] Synthesis of Mat 42

The procedure of Synthesis Example 13 was repeated except for using the d-2 compound obtained in Preparation Example 4 as a reactant, to obtain 4.8 g of the title compound.

HRMS [M] < + >: 698.19

[ Synthetic example  43] Synthesis of Mat 43

The procedure of Synthesis Example 14 was repeated except for using the compound d-2 obtained in Preparation Example 4 as a reactant, to obtain 4.7 g of the title compound.

HRMS [M] < + >: 712.16

[ Synthetic example  44] Synthesis of Mat 44

The procedure of Synthesis Example 15 was repeated except for using the compound d-2 obtained in Preparation Example 4 as a reactant, to obtain 6.1 g of the title compound.

HRMS [M] < + >: 777.20

[ Synthetic example  45] Synthesis of Mat 45

The procedure of Synthesis Example 16 was repeated except for using the d-3 compound obtained in Preparation Example 4 as a reactant, to obtain 6.7 g of the title compound.

HRMS [M] < + >: 853.23

[ Synthetic example  46] Synthesis of Mat 46

The procedure of Synthesis Example 17 was repeated except for using the d-4 compound obtained in Preparation Example 4 as a reactant, to obtain 7.1 g of the title compound.

HRMS [M] < + >: 932.29

[ Synthetic example  47] Synthesis of Mat 47

The procedure of Synthesis Example 18 was repeated except that the e-1 compound obtained in Preparation Example 5 was used as a reactant, to thereby yield the object compound (5.5 g).

HRMS [M] < + >: 698.19

[ Synthetic example  48] Synthesis of Mat 48

The procedure of Synthesis Example 19 was repeated except that the e-1 compound obtained in Preparation Example 5 was used as a reactant, to obtain 4.6 g of the title compound.

HRMS [M] < + >: 726.14

[ Synthetic example  49] Synthesis of Mat 49

The procedure of Synthesis Example 20 was repeated except that the e-1 compound obtained in Preparation Example 5 was used as a reactant, to obtain 5.2 g of the target compound.

HRMS [M] < + >: 758.10

[ Synthetic example  50] Synthesis of Mat 50

The procedure of Synthesis Example 21 was repeated except for using e-2 obtained in Preparation Example 5 as a reactant, to obtain 5.9 g of the title compound.

HRMS [M] < + >: 698.19

[ Synthetic example  51] Synthesis of Mat 51

The procedure of Synthesis Example 22 was repeated except that the e-3 compound obtained in Preparation Example 5 was used as a reactant, and 6.5 g of the title compound was obtained.

HRMS [M] < + >: 853.23

[ Synthetic example  52] Synthesis of Mat 52

The procedure of Synthesis Example 23 was repeated except that the e-3 compound obtained in Preparation Example 5 was used as a reactant to obtain the desired compound (7.7 g).

HRMS [M] < + >: 867.21

[ Synthetic example  53] Synthesis of Mat 53

The procedure of Synthesis Example 24 was repeated except for using the compound f-1 obtained in Preparation Example 6 as a reactant, to obtain 4.9 g of the title compound.

HRMS [M] < + >: 698.19

[ Synthetic example  54] Synthesis of Mat 54

The procedure of Synthesis Example 25 was repeated except that the f-1 compound obtained in Preparation Example 6 was used as a reactant, to obtain 6.78 g of the title compound.

HRMS [M] < + >: 726.14

[ Synthetic example  55] Synthesis of Mat 55

The procedure of Synthesis Example 26 was repeated except that the f-1 compound obtained in Preparation Example 6 was used as a reactant, to obtain 6.4 g of the desired compound.

HRMS [M] < + >: 758.10

[ Synthetic example  56] Synthesis of Mat 56

The same procedure as in Synthesis Example 27 was carried out except that the f-2 compound obtained in Preparation Example 6 was used as a reactant, to obtain 5.7 g of the title compound.

HRMS [M] < + >: 698.19

[ Synthetic example  57] Synthesis of Mat 57

The procedure of Synthesis Example 28 was repeated except that the f-3 compound obtained in Preparation Example 6 was used as a reactant, to obtain 4.3 g of the target compound.

HRMS [M] < + >: 853.23

[ Synthetic example  58] Synthesis of Mat 58

The procedure of Synthesis Example 29 was repeated except that the f-3 compound obtained in Preparation Example 6 was used as a reactant, to obtain 6.3 g of the target compound.

HRMS [M] < + >: 867.21

[ Synthetic example  59] Synthesis of Mat 59

The procedure of Synthesis Example 1 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 4.5 g of the title compound.

HRMS [M] < + >: 566.27

[ Synthetic example  60] Synthesis of Mat 60

The procedure of Synthesis Example 2 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 6.1 g of the title compound.

HRMS [M] < + >: 718.33

[ Synthetic example  61] Synthesis of Mat 61

The procedure of Synthesis Example 3 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 5.5 g of the title compound.

HRMS [M] < + >: 718.33

[ Synthetic example  62] Synthesis of Mat 62

The procedure of Synthesis Example 4 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 6.7 g of the title compound.

HRMS [M] < + >: 870.40

[ Synthetic example  63] Synthesis of Mat 63

The procedure of Synthesis Example 5 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 6.4 g of the title compound.

HRMS [M] < + >: 746.29

[ Synthetic example  64] Synthesis of Mat 64

The procedure of Synthesis Example 6 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, and 7.5 g of the desired compound was obtained.

HRMS [M] < + >: 798.40

[ Synthetic example  65] Synthesis of Mat 65

The procedure of Synthesis Example 7 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 7.7 g of the title compound.

HRMS [M] < + >: 896.39

[ Synthetic example  66] Synthesis of Mat 66

The procedure of Synthesis Example 8 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 6.8 g of the desired compound.

HRMS [M] < + >: 896.39

[ Synthetic example  67] Synthesis of Mat 67

The procedure of Synthesis Example 9 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 6.9 g of the title compound.

HRMS [M] < + >: 778.25

[ Synthetic example  68] Synthesis of Mat 68

The procedure of Synthesis Example 10 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 10.4 g of the title compound.

HRMS [M] < + >: 918.40

[ Synthetic example  69] Mat69's  synthesis

The procedure of Synthesis Example 11 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 8.8 g of the title compound.

HRMS [M] < + >: 876.37

[ Synthetic example  70] Synthesis of Mat 70

The procedure of Synthesis Example 12 was repeated except that the g-1 compound obtained in Preparation Example 7 was used as a reactant, to obtain 11.3 g of the title compound.

HRMS [M] < + >: 1028.43

[ Synthetic example  71] Synthesis of Mat 71

The procedure of Synthesis Example 13 was repeated except that the g-2 compound obtained in Preparation Example 7 was used as a reactant, to obtain 6.9 g of the title compound.

HRMS [M] < + >: 718.33

[ Synthetic example  72] Synthesis of Mat 72

The procedure of Synthesis Example 14 was repeated except that the g-2 compound obtained in Preparation Example 7 was used as a reactant, to obtain 6.2 g of the title compound.

HRMS [M] < + >: 732.31

[ Synthetic example  73] Synthesis of Mat 73

The procedure of Synthesis Example 15 was repeated except that the g-2 compound obtained in Preparation Example 7 was used as a reactant, to obtain 6.9 g of the title compound.

HRMS [M] < + >: 797.35

[ Synthetic example  74] Synthesis of Mat 74

The procedure of Synthesis Example 16 was repeated except that the g-3 compound obtained in Preparation Example 7 was used as a reactant, to obtain 7.3 g of the target compound.

HRMS [M] < + >: 873.38

[ Synthetic example  75] Synthesis of Mat 75

The procedure of Synthesis Example 17 was repeated except that the g-4 compound obtained in Preparation Example 7 was used as a reactant, to obtain 8.9 g of the title compound.

HRMS [M] < + >: 952.40

[ Synthetic example  76] Synthesis of Mat 76

The procedure of Synthesis Example 18 was repeated except for using the h-1 compound obtained in Preparation Example 8 as a reactant, to obtain 6.6 g of the title compound.

HRMS [M] < + >: 718.33

[ Synthetic example  77] Synthesis of Mat 77

The procedure of Synthesis Example 19 was repeated except for using the compound h-1 obtained in Preparation Example 8 as a reactant, to obtain 7.3 g of the target compound.

HRMS [M] < + >: 746.29

[ Synthetic example  78] Synthesis of Mat 78

The procedure of Synthesis Example 20 was repeated except for using the h-1 compound obtained in Preparation Example 8 as a reactant, to obtain 6.5 g of the title compound.

HRMS [M] < + >: 778.25

[ Synthetic example  79] Synthesis of Mat 79

The procedure of Synthesis Example 21 was repeated except for using the h-2 compound obtained in Preparation Example 8 as a reactant, to obtain 5.8 g of the title compound.

HRMS [M] < + >: 718.33

[ Synthetic example  80] Synthesis of Mat 80

The procedure of Synthesis Example 22 was repeated except for using the h-3 compound obtained in Preparation Example 8 as a reactant, to obtain 7.9 g of the title compound.

HRMS [M] < + >: 873.38

[ Synthetic example  81] Synthesis of Mat 81

The procedure of Synthesis Example 23 was repeated except for using the h-3 compound obtained in Preparation Example 8 as a reactant, to obtain 8.3 g of the target compound.

HRMS [M] < + >: 887.36

[ Synthetic example  82] Synthesis of Mat 82

The procedure of Synthesis Example 24 was repeated, except that the i-1 compound obtained in Preparation Example 9 was used as a reactant, to obtain 7.1 g of the title compound.

HRMS [M] < + >: 718.33

[ Synthetic example  83] Synthesis of Mat 83

The procedure of Synthesis Example 25 was repeated except for using the i-1 compound obtained in Preparation Example 9 as a reactant, to obtain 6.9 g of the title compound.

HRMS [M] < + >: 746.29

[ Synthetic example  84] Synthesis of Mat 84

The procedure of Synthesis Example 26 was repeated except that the i-1 compound obtained in Preparation Example 9 was used as a reactant, to obtain 6.5 g of the title compound.

HRMS [M] < + >: 778.25

[ Synthetic example  85] Synthesis of Mat 85

The procedure of Synthesis Example 27 was repeated except that the i-2 compound obtained in Preparation Example 9 was used as a reactant, to obtain 6.6 g of the title compound.

HRMS [M] < + >: 718.33

[ Synthetic example  86] Synthesis of Mat 86

The procedure of Synthesis Example 28 was repeated, except that the i-3 compound obtained in Preparation Example 9 was used as a reactant, to obtain 7.5 g of the title compound.

HRMS [M] < + >: 873.38

[ Synthetic example  87] Synthesis of Mat 87

The procedure of Synthesis Example 29 was repeated, except that the i-3 compound obtained in Preparation Example 9 was used as a reactant, to obtain 7.8 g of the title compound.

HRMS [M] < + >: 887.36

[ Synthetic example  88] Synthesis of Mat 88

The procedure of Synthesis Example 1 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 5.3 g of the target compound.

HRMS [M] < + >: 690.30

[ Synthetic example  89] Synthesis of Mat 89

The procedure of Synthesis Example 2 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 6.2 g of the target compound.

HRMS [M] < + >: 842.37

[ Synthetic example  90] Synthesis of Mat 90

The procedure of Synthesis Example 3 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 5.7 g of the title compound.

HRMS [M] < + >: 842.37

[ Synthetic example  91] Synthesis of Mat 91

The procedure of Synthesis Example 4 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 8.4 g of the title compound.

HRMS [M] < + >: 994.43

[ Synthetic example  92] Synthesis of Mat 92

The procedure of Synthesis Example 5 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 7.1 g of the title compound.

HRMS [M] < + >: 870.32

[ Synthetic example  93] Synthesis of Mat 93

The procedure of Synthesis Example 6 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 7.7 g of the title compound.

HRMS [M] < + >: 922.43

[ Synthetic example  94] Synthesis of Mat 94

The procedure of Synthesis Example 7 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant to obtain 11.6 g of the title compound.

HRMS [M] < + >: 1020.42

[ Synthetic example  95] Synthesis of Mat 95

The procedure of Synthesis Example 8 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 12.3 g of the desired compound.

HRMS [M] < + >: 1020.42

[ Synthetic example  96] Synthesis of Mat 96

The procedure of Synthesis Example 9 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 9.3 g of the title compound.

HRMS [M] < + >: 902.28

[ Synthetic example  97] Synthesis of Mat 97

The procedure of Synthesis Example 10 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 11.6 g of the title compound.

HRMS [M] < + >: 1042.43

[ Synthetic example  98] Mat98  synthesis

The procedure of Synthesis Example 11 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 10.4 g of the title compound.

HRMS [M] < + >: 1000.40

[ Synthetic example  99] Synthesis of Mat 99

The procedure of Synthesis Example 12 was repeated except that the j-1 compound obtained in Preparation Example 10 was used as a reactant, to obtain 12.6 g of the title compound.

HRMS [M] < + >: 1052.46

[ Synthetic example  100] Synthesis of Mat 100

The procedure of Synthesis Example 13 was repeated except that the j-2 compound obtained in Preparation Example 10 was used as a reactant, to obtain 6.8 g of the title compound.

HRMS [M] < + >: 842.37

[ Synthetic example  101] Synthesis of Mat 101

The procedure of Synthesis Example 14 was repeated except that the j-2 compound obtained in Preparation Example 10 was used as a reactant, to obtain 7.1 g of the title compound.

HRMS [M] < + >: 856.35

[ Synthetic example  102] Synthesis of Mat 102

The procedure of Synthesis Example 15 was repeated except that the j-2 compound obtained in Preparation Example 10 was used as a reactant, to obtain 6.6 g of the title compound.

HRMS [M] < + >: 921.38

[ Synthetic example  103] Synthesis of Mat 103

The procedure of Synthesis Example 16 was repeated except that the j-3 compound obtained in Preparation Example 10 was used as a reactant, to obtain 10.2 g of the title compound.

HRMS [M] < + >: 997.41

[ Synthetic example  104] Synthesis of Mat 104

The procedure of Synthesis Example 17 was repeated except that the j-4 compound obtained in Preparation Example 10 was used as a reactant, to obtain 11.4 g of the desired compound.

HRMS [M] < + >: 1076.43

[ Synthetic example  105] Synthesis of Mat 105

The procedure of Synthesis Example 18 was repeated except that the reaction mixture was replaced with the k-1 compound obtained in Preparation Example 11 to obtain the desired compound (7.2 g).

HRMS [M] < + >: 842.37

[ Synthetic example  106] Synthesis of Mat 106

The procedure of Synthesis Example 19 was repeated except that the k-1 compound obtained in Preparation Example 11 was used as a reactant, to obtain 8.3 g of the target compound.

HRMS [M] < + >: 870.32

[ Synthetic example  107] Synthesis of Mat 107

The procedure of Synthesis Example 20 was repeated except for using the compound (k-1) obtained in Preparation Example 11 as a reactant, to obtain 9.7 g of the title compound.

HRMS [M] < + >: 902.28

[ Synthetic example  108] Synthesis of Mat 108

The procedure of Synthesis Example 21 was repeated except that the k-2 compound obtained in Preparation Example 11 was used as a reactant, to obtain 8.7 g of the title compound.

HRMS [M] < + >: 842.37

[ Synthetic example  109] Synthesis of Mat 109

The procedure of Synthesis Example 22 was repeated except for using the compound (k-3) obtained in Preparation Example 11 as a reactant, to obtain 9.3 g of the title compound.

HRMS [M] < + >: 997.41

[ Synthetic example  110] Synthesis of Mat 110

The procedure of Synthesis Example 23 was repeated except for using the compound (k-3) obtained in Preparation Example 11 as a reactant to obtain the desired compound (10.9 g).

HRMS [M] < + >: 1011.39

[ Synthetic example  111] Synthesis of Mat 111

The procedure of Synthesis Example 24 was repeated except for using the compound I-1 obtained in Preparation Example 12 as a reactant, to obtain 6.1 g of the title compound.

HRMS [M] < + >: 842.37

[ Synthetic example  112] Synthesis of Mat 112

The procedure of Synthesis Example 25 was repeated except for using the compound I-1 obtained in Preparation Example 12 as a reactant to obtain 7 g of the title compound.

HRMS [M] < + >: 970.32

[ Synthetic example  113] Synthesis of Mat 113

The procedure of Synthesis Example 26 was repeated except for using the compound l-1 obtained in Preparation Example 12 as a reactant, to obtain 7.4 g of the objective compound.

HRMS [M] < + >: 902.28

[ Synthetic example  114] Synthesis of Mat 114

The procedure of Synthesis Example 27 was repeated except that the l-2 compound obtained in Preparation Example 12 was used as a reactant, to obtain 8.7 g of the title compound.

HRMS [M] < + >: 842.37

[ Synthetic example  115] Synthesis of Mat 115

The procedure of Synthesis Example 28 was repeated except for using the compound I-3 obtained in Preparation Example 12 as a reactant, to obtain 9.1 g of the title compound.

HRMS [M] < + >: 997.41

[ Synthetic example  116] Synthesis of Mat 116

The procedure of Synthesis Example 29 was repeated except for using the compound I-3 obtained in Preparation Example 12 as a reactant to obtain 11.6 g of the title compound.

HRMS [M] < + >: 1011.39

[ Synthetic example  117] Synthesis of Mat 117

The procedure of Synthesis Example 1 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 4.1 g of the title compound.

HRMS [M] < + >: 664.21

[ Synthetic example  118] Synthesis of Mat 118

The procedure of Synthesis Example 2 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 5.8 g of the title compound.

HRMS [M] < + >: 816.33

[ Synthetic example  119] Synthesis of Mat 119

The procedure of Synthesis Example 3 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 6.4 g of the desired compound.

HRMS [M] < + >: 816.33

[ Synthetic example  120] Synthesis of Mat 120

The procedure of Synthesis Example 4 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, and 7.5 g of the desired compound was obtained.

HRMS [M] < + >: 968.39

[ Synthetic example  121] Synthesis of Mat 121

The procedure of Synthesis Example 5 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 6.4 g of the title compound.

HRMS [M] < + >: 844.28

[ Synthetic example  122] Synthesis of Mat 122

The procedure of Synthesis Example 6 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 7.5 g of the title compound.

HRMS [M] < + >: 896.39

[ Synthetic example  123] Synthesis of Mat 123

The procedure of Synthesis Example 7 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 9.1 g of the title compound.

HRMS [M] < + >: 994.38

[ Synthetic example  124] Synthesis of Mat 124

The procedure of Synthesis Example 8 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 7.7 g of the title compound.

HRMS [M] < + >: 994.38

[ Synthetic example  125] Synthesis of Mat 125

The procedure of Synthesis Example 9 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 8.4 g of the target compound.

HRMS [M] < + >: 876.24

[ Synthetic example  126] Synthesis of Mat 126

The procedure of Synthesis Example 10 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 10.8 g of the title compound.

HRMS [M] < + >: 1016.39

[ Synthetic example  127] Mat127's  synthesis

The procedure of Synthesis Example 11 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to thereby yield 9.4 g of the target compound.

HRMS [M] < + >: 974.36

[ Synthetic example  128] Synthesis of Mat 128

The procedure of Synthesis Example 12 was repeated except that the m-1 compound obtained in Preparation Example 13 was used as a reactant, to obtain 10.3 g of the desired compound.

HRMS [M] < + >: 1126.42

[ Synthetic example  129] Synthesis of Mat 129

The procedure of Synthesis Example 13 was repeated except that the m-2 compound obtained in Preparation Example 13 was used as a reactant, to obtain 7.8 g of the target compound.

HRMS [M] < + >: 816.33

[ Synthetic example  130] Synthesis of Mat 130

The procedure of Synthesis Example 14 was repeated except that the m-2 compound obtained in Preparation Example 13 was used as a reactant, to obtain 8.8 g of the title compound.

HRMS [M] < + >: 830.30

[ Synthetic example  131] Synthesis of Mat 131

The procedure of Synthesis Example 15 was repeated except that the m-2 compound obtained in Preparation Example 13 was used as a reactant, to obtain the desired compound (10.6 g).

HRMS [M] < + >: 985.34

[ Synthetic example  132] Synthesis of Mat 132

The same procedure as in Synthesis Example 16 was carried out except that the m-3 compound obtained in Preparation Example 13 was used as a reactant, to obtain 10 g of the title compound.

HRMS [M] < + >: 971.37

[ Synthetic example  133] Synthesis of Mat 133

The procedure of Synthesis Example 17 was repeated except that the m-4 compound obtained in Preparation Example 13 was used as a reactant, to obtain 11.1 g of the title compound.

HRMS [M] < + >: 1050.39

[ Synthetic example  134] Synthesis of Mat 134

The procedure of Synthesis Example 18 was repeated except that n-1 compound obtained in Preparation Example 14 was used as a reactant, to obtain 5.0 g of the title compound.

HRMS [M] < + >: 816.33

[ Synthetic example  135] Synthesis of Mat 135

The procedure of Synthesis Example 19 was repeated except for using the n-1 compound obtained in Preparation Example 14 as a reactant, to obtain the object compound (5.5 g).

HRMS [M] < + >: 844.28

[ Synthetic example  136] Synthesis of Mat 136

The procedure of Synthesis Example 20 was repeated except for using the n-1 compound obtained in Preparation Example 14 as a reactant, to obtain 6.5 g of the title compound.

HRMS [M] < + >: 876.24

[ Synthetic example  137] Synthesis of Mat 137

The procedure of Synthesis Example 21 was repeated except for using the n-2 compound obtained in Preparation Example 14 as a reactant, to obtain 7.3 g of the target compound.

HRMS [M] < + >: 816.33

[ Synthetic example  138] Synthesis of Mat 138

The procedure of Synthesis Example 22 was repeated except for using the n-3 compound obtained in Preparation Example 14 as a reactant, to obtain 8.7 g of the title compound.

HRMS [M] < + >: 971.37

[ Synthetic example  139] Synthesis of Mat 139

The procedure of Synthesis Example 23 was repeated except for using the n-3 compound obtained in Preparation Example 14 as a reactant, to obtain 8.3 g of the target compound.

HRMS [M] < + >: 985.33

[ Synthetic example  140] Synthesis of Mat 140

The procedure of Synthesis Example 24 was repeated except for using the o-1 compound obtained in Preparation Example 15 as a reactant, to obtain 6.6 g of the title compound.

HRMS [M] < + >: 816.33

[ Synthetic example  141] Synthesis of Mat 141

The procedure of Synthesis Example 25 was repeated except for using the o-1 compound obtained in Preparation Example 15 as a reactant, to obtain 6.9 g of the title compound.

HRMS [M] < + >: 844.28

[ Synthetic example  142] Synthesis of Mat 142

The procedure of Synthesis Example 26 was repeated except that the o-1 compound obtained in Preparation Example 15 was used as a reactant, to obtain 7.6 g of the title compound.

HRMS [M] < + >: 876.24

[ Synthetic example  143] Synthesis of Mat 143

The procedure of Synthesis Example 27 was repeated except for using the o-2 compound obtained in Preparation Example 15 as a reactant, to obtain 7.8 g of the title compound.

HRMS [M] < + >: 816.33

[ Synthetic example  144] Synthesis of Mat 144

The procedure of Synthesis Example 28 was repeated except for using the o-3 compound obtained in Preparation Example 15 as a reactant, to obtain 8.5 g of the target compound.

HRMS [M] < + >: 971.37

[ Synthetic example  145] Synthesis of Mat 145

The procedure of Synthesis Example 29 was repeated except that the o-3 compound obtained in Preparation Example 15 was used as a reactant, to obtain 9.2 g of the title compound.

HRMS [M] < + >: 985.35

[ Synthetic example  146] Synthesis of Mat 146

The procedure of Synthesis Example 2 was repeated except that the P-1 compound obtained in Preparation Example 16 was used as a reactant, to obtain 5.4 g of the title compound.

HRMS [M] < + >: 692.28

[ Synthetic example  147] Synthesis of Mat 147

The procedure of Synthesis Example 5 was repeated except that the P-1 compound obtained in Preparation Example 16 was used as a reactant, to obtain 5.6 g of the title compound.

HRMS [M] < + >: 720.24

[ Synthetic example  148] Synthesis of Mat 148

The procedure of Synthesis Example 8 was repeated except that P-1 compound obtained in Preparation Example 16 was used as a reactant, to obtain 7.1 g of the desired compound.

HRMS [M] < + >: 870.34

[ Synthetic example  149] Synthesis of Mat 149

The procedure of Synthesis Example 9 was repeated except for using the P-1 compound obtained in Preparation Example 16 as a reactant, to obtain 6.9 g of the title compound.

HRMS [M] < + >: 752.20

[ Synthetic example  150] Synthesis of Mat 150

The procedure of Synthesis Example 12 was repeated, except that the P-1 compound obtained in Preparation Example 16 was used as a reactant, to obtain 11.8 g of the title compound.

HRMS [M] < + >: 1002.38

[ Synthetic example  151] Synthesis of Mat 151

The same procedure as in Synthesis Example 13 was carried out except that the P-2 compound obtained in Preparation Example 16 was used as a reactant to obtain 6 g of the target compound;

HRMS [M] < + >: 692.28

[ Synthetic example  152] Synthesis of Mat 152

The procedure of Synthesis Example 14 was repeated except for using the P-2 compound obtained in Preparation Example 16 as a reactant, to obtain 6.6 g of the desired compound.

HRMS [M] < + >: 706.26

[ Synthetic example  153] Synthesis of Mat 153

The procedure of Synthesis Example 16 was repeated except that the P-3 compound obtained in Preparation Example 16 was used as a reactant, to obtain 7.3 g of the target compound.

HRMS [M] < + >: 847.33

[ Synthetic example  154] Synthesis of Mat 154

The procedure of Synthesis Example 18 was repeated except that the reaction mixture was replaced with the compound q-1 obtained in Preparation Example 17 to obtain 5.2 g of the title compound.

HRMS [M] < + >: 692.28

[ Synthetic example  155] Synthesis of Mat 155

The procedure of Synthesis Example 19 was repeated except for using the compound q-1 obtained in Preparation Example 17 as a reactant to obtain 6 g of the target compound.

HRMS [M] < + >: 720.24

[Synthesis Example 156] Synthesis of Mat 156

The procedure of Synthesis Example 20 was repeated except for using the compound q-1 obtained in Preparation Example 17 as a reactant, to obtain 6.3 g of the target compound.

HRMS [M] < + >: 752.20

[Synthesis Example 157] Synthesis of Mat 157

The same procedure as in Synthesis Example 21 was carried out except that the reaction mixture was replaced with the q-2 compound obtained in Preparation Example 17 to obtain the desired compound (5.6 g).

HRMS [M] < + >: 692.28

[Synthesis Example 158] Synthesis of Mat 158

The procedure of Synthesis Example 22 was repeated except for using the compound q-3 obtained in Preparation Example 17 as a reactant, to obtain 8.2 g of the title compound.

HRMS [M] < + >: 847.33

[Synthesis Example 159] Synthesis of Mat 159

The procedure of Synthesis Example 24 was repeated except that the r-1 compound obtained in Preparation Example 18 was used as a reactant, to obtain 7.7 g of the title compound.

HRMS [M] < + >: 692.28

[Synthesis Example 160] Synthesis of Mat 160

The procedure of Synthesis Example 25 was repeated except that the r-1 compound obtained in Preparation Example 18 was used as a reactant, to obtain 5.87 g of the desired compound.

HRMS [M] < + >: 720.24

[Synthesis Example 161] Synthesis of Mat 161

The procedure of Synthesis Example 26 was repeated except that the r-1 compound obtained in Preparation Example 18 was used as a reactant, to obtain 6.9 g of the title compound.

HRMS [M] < + >: 753.20

[Synthesis Example 162] Synthesis of Mat 162

The procedure of Synthesis Example 27 was repeated except that the r-2 compound obtained in Preparation Example 18 was used as a reactant, to thereby obtain 7.5 g of the title compound.

HRMS [M] < + >: 692.28

[Synthesis Example 163] Synthesis of Mat 163

The procedure of Synthesis Example 28 was repeated, except that the r-3 compound obtained in Preparation Example 18 was used as a reactant, to thereby yield 11 g of the target compound.

HRMS [M] < + >: 847.33

[Synthesis Example 164] Synthesis of Mat 164

The procedure of Synthesis Example 2 was repeated except that the s-1 compound obtained in Preparation Example 19 was used as a reactant, to thereby yield 7 g of the title compound.

HRMS [M] < + >: 754.30

[Synthesis Example 165] Synthesis of Mat 165

The procedure of Synthesis Example 13 was repeated except for using the s-2 compound obtained in Preparation Example 19 as a reactant, to obtain 6.9 g of the desired compound.

HRMS [M] < + >: 754.30

[Synthesis Example 166] Synthesis of Mat 166

The procedure of Synthesis Example 18 was repeated except that t-1 compound obtained in Preparation Example 20 was used as a reactant, to obtain 7.7 g of the title compound. HRMS [M] < + >: 754.30

[Synthesis Example 167] Synthesis of Mat 167

The procedure of Synthesis Example 21 was repeated except that the t-2 compound obtained in Preparation Example 20 was used as a reactant, to thereby yield 7 g of the target compound.

HRMS [M] < + >: 754.30

[Synthesis Example 168] Synthesis of Mat 168

The procedure of Synthesis Example 2 was repeated except for using the u-1 compound obtained in Preparation Example 21 as a reactant, to obtain 6.6 g of the title compound.

HRMS [M] < + >: 770.28

[Synthesis Example 169] Synthesis of Mat 169

The procedure of Synthesis Example 13 was repeated except that the u-2 compound obtained in Preparation Example 21 was used as a reactant, to obtain 7.3 g of the target compound.

HRMS [M] < + >: 770.28

[Synthesis Example 170] Synthesis of Mat 170

The same procedure as in Synthesis Example 18 was carried out except that the reaction mixture was replaced with the v-1 compound obtained in Preparation Example 22, thereby obtaining 6 g of the target compound.

HRMS [M] < + >: 770.28

[Synthesis Example 171] Synthesis of Mat 171

The procedure of Synthesis Example 21 was repeated except that the v-2 compound obtained in Preparation Example 22 was used as a reactant, to obtain 6.8 g of the target compound.

HRMS [M] < + >: 770.28

[Synthesis Example 172] Synthesis of Mat 172

The procedure of Synthesis Example 2 was repeated except that the w-1 compound obtained in Preparation Example 23 was used as a reactant, to obtain 7.9 g of the title compound.

HRMS [M] < + >: 767.33

[Synthesis Example 173] Synthesis of Mat 173

The procedure of Synthesis Example 5 was repeated except that the w-1 compound obtained in Preparation Example 23 was used as a reactant, to obtain 6.8 g of the title compound.

HRMS [M] < + >: 795.29

[Synthesis Example 174] Synthesis of Mat 174

The procedure of Synthesis Example 8 was repeated except for using the compound (w-1) obtained in Preparation Example 23 as a reactant to obtain the object compound (7.4 g).

HRMS [M] < + >: 945.38

[Synthesis Example 175] Synthesis of Mat 175

The same procedure as in Synthesis Example 9 was carried out except that w-1 compound obtained in Preparation Example 23 was used as a reactant, to obtain 8.3 g of the target compound.

HRMS [M] < + >: 827.24

[Synthesis Example 176] Synthesis of Mat 176

The procedure of Synthesis Example 12 was repeated except that the w-1 compound obtained in Preparation Example 23 was used as a reactant to obtain 12 g of the title compound.

HRMS [M] < + >: 1077.43

[Synthesis Example 177] Synthesis of Mat 177

The procedure of Synthesis Example 13 was repeated except for using the w-2 compound obtained in Preparation Example 23 as a reactant, to obtain 8.5 g of the target compound.

HRMS [M] < + >: 767.33

[Synthesis Example 178] Synthesis of Mat 178

The procedure of Synthesis Example 14 was repeated except that the w-2 compound obtained in Preparation Example 23 was used as a reactant, to obtain 8.7 g of the title compound.

HRMS [M] < + >: 781.31

[Synthesis Example 179] Synthesis of Mat 179

The procedure of Synthesis Example 16 was repeated except that the w-3 compound obtained in Preparation Example 23 was used as a reactant, to obtain 8.6 g of the title compound.

HRMS [M] < + >: 922.38

[Synthesis Example 180] Synthesis of Mat 180

The procedure of Synthesis Example 18 was repeated except that the reaction mixture was replaced with the x-1 compound obtained in Preparation Example 24 to obtain the desired compound (8.1 g).

HRMS [M] < + >: 767.33

[Synthesis Example 181] Synthesis of Mat 181

The procedure of Synthesis Example 19 was repeated except that the reaction mixture was replaced with the x-1 compound obtained in Preparation Example 24 to obtain the desired compound (7.8 g).

HRMS [M] < + >: 795.29

[Synthesis Example 182] Synthesis of Mat 182

The procedure of Synthesis Example 20 was repeated except that the reaction mixture was replaced with the x-1 compound obtained in Preparation Example 24 to obtain 9.4 g of the title compound.

HRMS [M] < + >: 827.24

[Synthesis Example 183] Synthesis of Mat 183

The procedure of Synthesis Example 21 was repeated to obtain the desired compound (10.7 g), except that the x-2 compound obtained in Preparation Example 24 was used as the reactant.

HRMS [M] < + >: 767.33

[Synthesis Example 184] Synthesis of Mat 184

The procedure of Synthesis Example 22 was repeated, except that the reaction mixture was replaced with the x-3 compound obtained in Preparation Example 24 to obtain the desired compound (12 g).

HRMS [M] < + >: 922.38

[Synthesis Example 185] Synthesis of Mat 185

The same procedure as in Synthesis Example 24 was carried out except that the reaction mixture was replaced with the y-1 compound obtained in Preparation Example 25 to obtain the desired compound (8.3 g).

HRMS [M] < + >: 767.33

[Synthesis Example 186] Synthesis of Mat 186

The procedure of Synthesis Example 25 was repeated except for using the compound y-1 obtained in Preparation Example 25 as a reactant, to obtain 8.6 g of the title compound.

HRMS [M] < + >: 795.29

[Synthesis Example 187] Synthesis of Mat 187

The procedure of Synthesis Example 26 was repeated except for using the compound y-1 obtained in Preparation Example 25 as a reactant, to obtain 9.6 g of the title compound.

HRMS [M] < + >: 827.24

[Synthesis Example 188] Synthesis of Mat 188

The procedure of Synthesis Example 27 was repeated except for using the y-2 compound obtained in Preparation Example 25 as a reactant, to obtain 10.5 g of the target compound.

HRMS [M] < + >: 767.33

[Synthesis Example 189] Synthesis of Mat 189

The procedure of Synthesis Example 28 was repeated except that the y-3 compound obtained in Preparation Example 25 was used as a reactant, to obtain 9.7 g of the title compound.

HRMS [M] < + >: 922.38

[Synthesis Example 190] Synthesis of Mat 190

The procedure of Synthesis Example 2 was repeated except that the z-1 compound obtained in Preparation Example 26 was used as a reactant, to obtain 9.8 g of the title compound.

HRMS [M] < + >: 829.35

[Synthesis Example 191] Synthesis of Mat 191

The procedure of Synthesis Example 13 was repeated except that the z-2 compound obtained in Preparation Example 26 was used as a reactant to obtain 11.7 g of the title compound.

HRMS [M] < + >: 829.35

[Synthesis Example 192] Synthesis of Mat 192

The procedure of Synthesis Example 18 was repeated except that the aa-1 compound obtained in Preparation Example 27 was used as a reactant, to obtain 10.2 g of the target compound.

HRMS [M] < + >: 829.35

[Synthesis Example 193] Synthesis of Mat 193

The procedure of Synthesis Example 21 was repeated except that the aa-2 compound obtained in Preparation Example 27 was used as a reactant, to obtain 12 g of the title compound.

HRMS [M] < + >: 829.35

[Examples 1 to 31] Preparation of green organic electroluminescent device

Compounds Mat 1 to Mat 193 synthesized in Synthesis Examples 1 to 193 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) / each compound described in Table 1 + 10% Ir (ppy) ₃ (30 nm) / BCP (10 nm) / Alq ₃ nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

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

[Comparative Example 1] Production of green organic electroluminescent device

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

[Evaluation Example 1]

Current efficiency and emission peak at current density (10) mA / cm < 2 > were measured for each of the green organic electroluminescent devices prepared in Examples 1 to 31 and Comparative Example 1, Respectively.

Sample Host Driving voltage
(V) EL peak
(nm) Current efficiency
(cd / A) Example 1 Mat 1 6.01 516 41.5 Example 2 Mat 2 6.23 516 39.2 Example 3 Mat 3 6.54 516 41.5 Example 4 Mat 4 6.28 515 39.1 Example 5 Mat 5 6.31 516 38.7 Example 6 Mat 8 6.48 516 39.2 Example 7 Mat 9 6.52 516 41.5 Example 8 Mat 17 6.87 516 39.1 Example 9 Mat 18 6.54 516 39.6 Example 10 Mat 22 6.28 516 41.5 Example 11 Mat 24 6.31 516 39.1 Example 12 Mat 28 6.01 516 39.6 Example 13 Mat 31 6.23 516 39.2 Example 14 Mat 41 6.28 515 42.8 Example 15 Mat 45 6.31 516 41.5 Example 16 Mat 50 6.28 516 39.1 Example 17 Mat 60 6.54 516 42.8 Example 18 Mat 72 6.01 516 41.5 Example 19 Mat 74 6.23 516 39.1 Example 20 Mat 82 6.48 516 39.2 Example 21 Mat 100 6.54 516 41.8 Example 22 Mat 105 6.54 516 39.2 Example 23 Mat 104 6.54 517 42.8 Example 24 Mat 124 6.01 516 41.5 Example 25 Mat 133 6.23 516 42.8 Example 26 Mat 138 6.01 516 41.5 Example 27 Mat 144 6.54 516 39.1 Example 28 Mat 153 6.54 516 39.6 Example 29 Mat 162 6.28 516 40.9 Example 30 Mat 166 6.31 516 41 Example 31 Mat 171 6.48 516 42 Comparative Example 1 CBP 6.93 516 38.2

As shown in Table 1, when the compound (Mat 1 to Mat 171) according to the present invention was used as a light emitting layer of a green organic electroluminescent device (Examples 1 to 31), 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).

[Examples 32 to 43] Preparation of red organic electroluminescent 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) / each 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] Production of red organic electroluminescent device

A red organic electroluminescent device was fabricated in the same manner as in Example 32 except that CBP was used instead of the compound of Mat 2 as a luminescent host material in forming the light emitting layer.

The structures of m-MTDATA, (piq) ₂ Ir (acac), CBP and BCP used in Examples 32 to 43 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 32 to 43 and Comparative Example 2, and the results are shown in Table 2 below.

Sample Host The driving voltage (V) Current efficiency (cd / A) Example 32 Mat 2 5.19 8.7 Example 33 Mat 16 5.08 8.4 Example 34 Mat 28 5.1 8.8 Example 35 Mat 41 5.02 9.2 Example 36 Mat 46 4.99 8.9 Example 37 Mat 58 4.97 8.2 Example 38 Mat 74 5.11 8.4 Example 39 Mat 81 5.02 8.5 Example 40 Mat 116 4.99 9.2 Example 41 Mat 132 4.98 8.7 Example 42 Mat 163 5.1 8.6 Example 43 Mat 189 5.01 9.1 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 for the light emitting layer of a red organic electroluminescent device (Examples 32 to 43), a red organic electroluminescent device using conventional CBP as a material for the light emitting layer 2), it can be seen that it shows excellent performance in terms of efficiency and driving voltage.

[Examples 44 to 51] Preparation of organic electroluminescent 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) / each compound (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq ₃ (30 nm) shown in the following Table 3 on the ITO transparent electrode prepared as described above ) / 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 44 except that NPB was used as the hole transport layer material instead of the compound Mat 1 used as the hole transport layer material in forming the hole transport layer in Example 44. [ 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 45 to 51 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 44 Mat 1 5.0 19.1 Example 45 Mat 4 4.9 19.8 Example 46 Mat 19 5.1 19.9 Example 47 Mat 33 4.8 19.3 Example 48 Mat 62 4.9 18.7 Example 49 Mat 91 4.8 19.2 Example 50 Mat 120 4.8 18.9 Example 51 Mat 160 4.9 18.6 Comparative Example 3 NPB 5.2 18.1

As shown in Table 3, the organic electroluminescent devices (organic electroluminescent devices manufactured in Examples 44 to 51, respectively) using the compounds (Mat 1 to Mat 160) according to the present invention as the hole transport layer, 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 (11)

A compound represented by the following general formula (4):
[Chemical Formula 4]

In Formula 4,
X ₁ and X ₂ are each independently O or S;
X ₃ is N (Ar ₁ ) and plural X ₃ are the same or different from each other;
A ₁ to A ₄ are both C (R ₉ ), plural A ₁ to A ₄ are the same or different from each other;
R ₉ is selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, and when R ₉ is plural, ;
Ar ₁ is selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms; when a plurality of Ar _{1 s} are present, they are the same or different;
The alkyl, aryl and heteroaryl groups of R ₉ and Ar ₁ are each independently selected from the group consisting of a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms And when they are substituted with a plurality of substituents, they may be the same or different.
The method according to claim 1,
Wherein Ar ₁ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms.
3. The method of claim 2,
Ar ₁ may be selected from the group consisting of phenyl, biphenyl, terphenyl, dibenzofuranyl, fluorenyl, carbazolyl and dibenzothiophenyl,
Wherein the phenyl, biphenyl, terphenyl, dibenzofuranyl, fluorenyl, carbazolyl and dibenzothiophenyl are each independently selected from the group consisting of methyl, ethyl, phenyl, biphenyl, phenanthrenyl and carbazolyl groups. 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 < ₉ > and Ar < ₁ > is a substituent represented by the following formula (6)
[Chemical Formula 6]

In Formula 6,
* Represents a moiety bound to the formula (4);
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;
Each of Z ₁ to Z ₅ is independently N or C (R ₁₀ ), or at least one of Z ₁ to Z ₅ is N;
R ₁₀ is selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or may be bonded to adjacent groups to form a condensed ring And when a plurality of R _{10 s} are present, they are the same or different;
Arylene group and a heteroarylene group, an alkyl group of the R ₁₀ of the L _1, aryl and heteroaryl groups are each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and the nuclear atoms of 5 to 60 of the And heteroaryl groups, and when they are substituted with a plurality of substituents, they may be the same or different from each other.
5. The method of claim 4,
The substituent represented by the formula (6) is a substituent represented by any one of the following A-1 to A-15:

In the above A-1 to A-15,
* Means a moiety bonded to Formula 4 above;
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;
R ₁₀ is selected from the group consisting of hydrogen, a C ₁ to C ₄₀ alkyl group, a C ₆ to C ₆₀ aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or may be bonded to adjacent groups to form a condensed ring And a plurality of R < ₁₀ > are the same or different from each other;
n is an integer of 0 to 4, and when n is 0, hydrogen means not substituted by substituent R ₁₁ , and when n is an integer of 1 to 4, R ₁₁ is a C ₁ to C ₄₀ alkyl group, An aryl group having ₆ to ₆₀ carbon atoms and a heteroaryl group having 5 to 60 ring atoms, or may be bonded to adjacent groups to form a condensed ring. When there are a plurality of R _{11 s} , they may be the same or different ;
The arylene group and a heteroarylene group, the R ₁₀ and the R alkyl group of _11, an aryl group and heteroaryl group each independently a C ₁ ~ C ₄₀ alkyl group, C ₆ ~ C ₆₀ aryl group and a nuclear atom of L ₁ A substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted heteroaryl group.
6. The method of claim 5,
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 ₁₁ is a substituted or unsubstituted C ₆ ~ C ₆₀ aryl group or a substituted or unsubstituted 5 to 60 nuclear atoms of the heteroaryl group in the compounds. delete delete The method according to claim 1,
Wherein the compound represented by Formula 4 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 (4). 11. The method of claim 10,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer, a life improving layer, a light emitting layer, and a light emitting auxiliary layer.