阅读说明：本技术 新的杂环化合物和使用其的有机发光器件 (Novel heterocyclic compound and organic light emitting device using the same ) 是由 李征夏 李东勋 朴胎润 赵圣美 许东旭 郑珉祐 于 2018-07-20 设计创作，主要内容包括：本发明涉及新的环状化合物和使用其的有机发光器件。(The present invention relates to a novel cyclic compound and an organic light emitting device using the same.)

1. A compound represented by the following formula 1:

[ formula 1]

Wherein, in the above formula 1,

X₁is O or S, and is a compound of,

R₁is hydrogen or substituted or unsubstituted C_1-60An alkyl group, a carboxyl group,

L₁and L₂Each independently being a direct bond or a substituted or unsubstituted C_6-60An arylene group, a cyclic or cyclic alkylene group,

Y₁、Y₂and Y₃Each independently is N or CR₂Provided that at least one of them is N, R₂Is hydrogen or substituted or unsubstituted C_1-60An alkyl group, a carboxyl group,

Ar₁and Ar₂Each independently is substituted or unsubstituted C_6-60Aryl or substituted or unsubstituted C comprising at least one of N, O and S_5-60Heteroaryl group capable of being linked to the adjacent Y₁、Y₂And Y₃Combine to form a ring which is,

each Het is independently a compound represented by the following formula 1-1:

[ formula 1-1]

Wherein, in the above formula 1-1,

b is O, S or NR₄；

Each R₃Independently hydrogen, substituted or unsubstituted C_1-60Alkyl, or substituted or unsubstituted C_6-60An aryl group, a heteroaryl group,

R₄is substituted or unsubstituted C_1-60Alkyl, or substituted or unsubstituted C_6-60Aryl, and

l is 1 or 2.

2. The compound according to claim 1, wherein the compound represented by formula 1-1 is any one selected from the group consisting of compounds represented by the following formulae 1-1-1 to 1-1-6:

wherein, in the above formulae 1-1-1 to 1-1-6,

R₃b and l are as defined in claim 1.

3. The compound of claim 1, wherein the Het is selected from any one of the following formulas:

4. the compound according to claim 1, wherein the compound represented by formula 1 is any one selected from compounds represented by the following formulae 2 to 6:

[ formula 2]

[ formula 3]

[ formula 4]

[ formula 5]

[ formula 6]

Wherein, in the above formulas 2 to 6,

X₁、L₁、L₂、Het、Y₁、Y₂、Y₃、R₁、Ar₁、Ar₂and n is as defined in claim 1.

5. The compound according to claim 1, wherein the compound represented by formula 1 is any one selected from compounds represented by the following formulae 7 to 9:

[ formula 7]

[ formula 8]

[ formula 9]

Wherein, in the above formulas 7 to 9,

X₁、L₁、L₂、Het、R₁n and m are as defined in claim 1.

6. The compound of claim 1, wherein R₁Is hydrogen or substituted or unsubstituted C_1-10An alkyl group.

7. The compound of claim 1, wherein R₃Is hydrogen or phenyl.

8. The compound of claim 1, wherein L₁And L₂Each independently is a direct bond or

9. The compound of claim 1, wherein Ar₁And Ar₂Each independently selected from the following formulae:

10. the compound according to claim 1, wherein the compound represented by formula 1 is any one selected from the group consisting of the following formulae:

11. an organic light emitting device comprising: a first electrode; a second electrode disposed on an opposite side of the first electrode; and at least one layer of organic material disposed between the first electrode and the second electrode, wherein the at least one layer of organic material comprises a compound according to any one of claims 1 to 10.

12. The organic light-emitting device according to claim 11, wherein the organic material layer containing the compound is a light-emitting layer.

13. An organic light-emitting device according to claim 12 wherein the compound is a host material in the light-emitting layer.

14. An organic light-emitting device according to claim 13 wherein the light-emitting layer further comprises a dopant material.

15. The organic light-emitting device according to claim 11, wherein the organic material layer containing the compound is an electron injection layer; an electron transport layer; or a layer that performs both electron injection and electron transport.

Technical Field

Cross Reference to Related Applications

The present application claims priority and benefit of korean patent application No. 10-2017-.

The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. Organic light emitting devices using the organic light emitting phenomenon have characteristics such as a wide viewing angle, excellent contrast, a fast response time, and excellent brightness, driving voltage, and response speed, and thus many studies have been made thereon.

An organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer interposed between the anode and the cathode. The organic material layer may have a multi-layer structure including different materials to improve efficiency and stability of the organic light emitting device, for example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic material layer and electrons are injected from a cathode into the organic material layer, excitons are formed when the injected holes and electrons meet each other, and light is emitted when the excitons fall to a ground state.

There is a continuing need to develop new materials for organic materials used in such organic light emitting devices.

[ Prior art documents ]

[ patent document ]

(patent document 0001) Korean patent laid-open publication No. 10-2013-073537

Disclosure of Invention

Technical problem

An object of the present invention is to provide a novel heterocyclic compound and an organic light emitting device comprising the same.

Technical scheme

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

[ formula 1]

In the above-mentioned formula 1, the,

X₁is O or S, and is a compound of,

R₁is hydrogen or substituted or unsubstituted C_1-60An alkyl group, a carboxyl group,

L₁and L₂Each independently being a direct bond or a substituted or unsubstituted C_6-60An arylene group, a cyclic or cyclic alkylene group,

Y₁、Y₂and Y₃Each independently is N or CR₂Provided that at least one of them is N, R₂Is hydrogen or substituted or unsubstituted C_1-60An alkyl group, a carboxyl group,

Ar₁and Ar₂Each independently is substituted or unsubstituted C_6-60Aryl or substituted or unsubstituted C comprising at least one of N, O and S_5-60Heteroaryl, which may be attached to the adjacent Y₁、Y₂And Y₃Combine to form a ring which is,

each Het is independently a compound represented by the following formula 1-1:

[ formula 1-1]

Wherein, in the above formula 1-1,

b is O, S or NR₄；

Each R₃Independently hydrogen, substituted or unsubstituted C_1-60Alkyl, or substituted or unsubstituted C_6-60An aryl group, a heteroaryl group,

R₄is substituted or unsubstituted C_1-60Alkyl, or substituted or unsubstituted C_6-60Aryl, and

l is 1 or 2.

The present invention also provides an organic light emitting device comprising: a first electrode; a second electrode disposed on an opposite side of the first electrode; and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the above-described compound of the present invention.

Advantageous effects

The compound represented by formula 1 described above may be used as a material of an organic material layer of an organic light emitting device, and may result in improved efficiency, low driving voltage, and/or lifetime characteristics when applied to the organic light emitting device. In particular, the compound represented by formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.

Drawings

Fig. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4.

Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4.

Detailed Description

Hereinafter, the present invention will be described in more detail to help understanding the present invention.

The present invention provides a compound represented by formula 1 below.

A compound represented by the following formula 1:

[ formula 1]

Wherein, in the above formula 1,

X₁is O or S, and is a compound of,

R₁is hydrogen or substituted or unsubstituted C_1-60An alkyl group, a carboxyl group,

L₁and L₂Each independently being a direct bond or a substituted or unsubstituted C_6-60An arylene group, a cyclic or cyclic alkylene group,

Y₁、Y₂and Y₃Each independently is N or CR₂Provided that at least one of them is N, R₂Is hydrogen or substituted or unsubstituted C_1-60An alkyl group, a carboxyl group,

Ar₁and Ar₂Each independently is substituted or unsubstituted C_6-60Aryl or substituted or unsubstituted C comprising at least one of N, O and S_5-60Heteroaryl, which may be attached to the adjacent Y₁、Y₂And Y₃Combine to form a ring which is,

each Het is independently a compound represented by the following formula 1-1:

[ formula 1-1]

Wherein, in the above formula 1-1,

b is O, S or NR₄；

Each R₃Independently hydrogen, substituted or unsubstituted C_1-60Alkyl, or substituted or unsubstituted C_6-60An aryl group, a heteroaryl group,

R₄is substituted or unsubstituted C_1-60Alkyl, or viaSubstituted or unsubstituted C_6-60Aryl, and

l is 1 or 2.

In the context of the present specification,

meaning a bond to another substituent.

As used herein, the term "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkylsulfonyl group; an arylsulfonyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or a heterocyclic group containing at least one of N, O and S atoms, or no substituent, or a substituent linked by two or more of the exemplified substituents, or no substituent. For example, the term "a substituent to which two or more substituents are attached" may be a biphenyl group. That is, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.

In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may have a structure in which the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes, but is not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like.

In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine and iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-butyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl, styryl and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. As the monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Examples of polycyclic aromatic groups include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, perylene,A phenyl group, a fluorenyl group, and the like, but are not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two may be substitutedThe substituents may be combined with each other to form a spiro ring structure. In the case of substituted fluorenyl radicals, may form

And the like. However, the structure is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl

Azolyl group,

Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.

In the present specification, the aryl group of the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the foregoing examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group and the alkylamino group is the same as the foregoing examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamino group may employ the aforementioned description of the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the foregoing example of the alkenyl group. In this specification, the foregoing description of aryl groups may be applied with the exception that the arylene group is a divalent group. In this specification, the foregoing description of heterocyclyl groups may be applied with the difference that the heteroarylene group is a divalent group. In this specification, the foregoing description of aryl or cycloalkyl groups may be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present specification, the foregoing description of heterocyclic groups may be applied, except that the heterocyclic group is not a monovalent group but is formed by combining two substituents.

Preferably, the compound represented by formula 1 may be any one selected from the group consisting of compounds represented by the following formulae 2 to 6.

[ formula 2]

[ formula 3]

[ formula 4]

[ formula 5]

[ formula 6]

In the above-mentioned formulas 2 to 6,

X₁、L₁、L₂、Het、Y₁、Y₂、Y₃、R₁、Ar₁、Ar₂and n is as defined above.

Further, more preferably, the compound of formula 1 may be a compound of formulae 2, 4 and 6.

Further, preferably, the compound of formula 1 may be any one selected from the group consisting of compounds represented by the following formulae 7 to 9.

[ formula 7]

[ formula 8]

[ formula 9]

In the above-mentioned formulas 7 to 9,

X₁、L₁、L₂、Het、R₁n and m are as defined above.

Preferably, in formula 1, R₁May be hydrogen or substituted or unsubstituted C_1-10Alkyl, more preferably hydrogen.

Preferably, in formula 1, L₁And L₂Each independently is a direct bond or

Preferably, in formula 1, Ar₁And Ar₂Each independently selected from the following formulae.

Preferably, sub-formula 1-1 of Het in sub-formula 1 may be any one selected from the group consisting of compounds represented by the following formulas 1-1-1 to 1-1-6.

In the above formulas 1-1-1 to 1-1-6,

R₃b and l are as defined above.

Preferably, in formula 1, R₃And may be hydrogen or phenyl.

Preferably, in formula 1, Het may be any one selected from the following formulae.

Preferably, the compound represented by formula 1 may be any one selected from the following formulae.

Since the compound represented by formula 1 has a structure having both a substituent substituted at the 1-position of the dibenzofuran (dibenzothiophene) core, such as triazine (pyridine, pyrimidine), and the above substituent Het, it is possible to exhibit excellent heat resistance and suppress crystallization during the operation of the device. Therefore, the organic light emitting device using the same may have high efficiency, low driving voltage, high luminance, long life, and the like.

The compound represented by formula 1 may be prepared according to a preparation method as shown in the following reaction scheme 1.

[ reaction scheme 1]

In reaction scheme 1, L₁、L₂、Y₁、Y₂、Y₃、Ar₁、Ar₂And Het is as defined above. The types of the reactive groups and the catalyst used in the above reaction scheme may be appropriately changed.

In addition, the present invention provides an organic light emitting device comprising the compound represented by formula 1. In one example, the present invention provides an organic light emitting device comprising: a first electrode; a second electrode disposed on an opposite side of the first electrode; and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by formula 1.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and it may include a smaller number of organic layers.

The organic material layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, wherein the hole injection layer, the hole transport layer, and the layer simultaneously performing hole injection and transport include the compound represented by formula 1.

The organic material layer may include a light emitting layer, wherein the light emitting layer includes a compound represented by formula 1.

The organic material layer may include an electron transport layer or an electron injection layer, wherein the electron transport layer or the electron injection layer includes the compound represented by formula 1.

The electron transport layer, the electron injection layer, and the layer simultaneously performing electron injection and electron transport include a compound represented by formula 1. In particular, the compound represented by formula 1 according to one embodiment of the present invention has excellent thermal stability, a deep HOMO level of 6.0eV or more, a high triplet Energy (ET), and hole stability. In addition, when the compound represented by formula 1 is used for an organic material layer capable of simultaneously performing electron injection and electron transport, an n-type dopant used in the art may be mixed and used.

The organic material layer may include a light emitting layer and an electron transport layer, wherein the electron transport layer may include a compound represented by formula 1.

The organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, at least one organic material layer, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, fig. 1 and 2 show the structure of an organic light emitting device according to an embodiment of the present invention.

Fig. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4. In such a structure, the compound represented by formula 1 may be contained in the light emitting layer.

Fig. 2 shows an example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4. In such a structure, the compound represented by formula 1 may be contained in at least one of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by the following process: an anode is formed by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a material that can be used as a cathode is deposited on the organic material layer. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, in manufacturing an organic light emitting element, the compound represented by formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (international publication WO 2003/012890). However, the manufacturing method is not limited thereto.

For example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

As the anode material, it is generally preferable to use a material having a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SNO₂Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.

As the cathode material, it is generally preferable to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO₂Al; and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound of: which has the ability to transport holes, a hole injection effect in an anode, and an excellent hole injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to an electron injection layer or an electron injection material, and has an excellent thin film forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanenitrile-based hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is suitably a material having a large hole mobility that can receive holes from the anode or the hole injection layer and transport the holes to the light emitting layer. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers in which a conjugated portion and a non-conjugated portion coexist, and the like, but are not limited thereto.

The light emitting material is a material capable of emitting light in a visible light region by combining holes and electrons respectively transported from the hole transport layer and the electron transport layer and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxy-quinolinylaluminum (Alq)₃) A complex; a carbazole-based compound; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-A metal compound; based on benzene

Oxazole, benzothiazole-based and benzimidazole-based compounds; polymers based on poly (p-phenylene vinylene) (PPV); a spiro compound; a polyfluorene; rubrene, and the like, but is not limited thereto.

The light emitting layer may include a host material and a dopant material, and the compound of the present invention may be included in the light emitting layer as the host material. The host material may be a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specific examples of the aromatic amine derivative include substituted or unsubstituted fused aromatic ring derivatives having an arylamino group, and examples thereof include pyrenes, anthracenes, anthracene, having an arylamino group,

And diindenoperene (periflanthene), etc., the styrene amine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. Further, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.

The electron transport layer is a layer which receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is a material which can well receive electrons from the cathode and transport the electrons to the light emitting layer, and hasMaterials with large electron mobility are suitable. Specific examples thereof include: 8-hydroxyquinoline Al complex; comprising Alq₃The complex of (1); an organic radical compound; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with a predetermined desired cathode material as used according to the prior art. Examples of suitable cathode materials are, in particular, the general materials having a low work function and being followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.

The electron injection layer is a layer that injects electrons from the electrode, and such a compound is preferable: which has an ability to transport electrons, an electron injection effect from a cathode, and an excellent electron injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to a hole injection layer, and has an excellent thin film forming ability. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and the like,Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compounds include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), chlorogallium bis (2-methyl-8-quinolinolato), gallium bis (2-methyl-8-quinolino) (o-cresol), aluminum bis (2-methyl-8-quinolino) (1-naphthol), gallium bis (2-methyl-8-quinolino) (2-naphthol), and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a front emission type, a rear emission type, or a double-sided emission type depending on the material used.

Further, the compound represented by formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.

In the following examples, the preparation of the compound represented by formula 1 and the organic light emitting device comprising the same will be described in detail. However, these examples are presented for illustrative purposes only, and the scope of the present invention is not limited thereto.

Preparation example 1

Preparation examples 1 to 1: synthesis of intermediate Compound A-4

1) Preparation of Compound A-1

1-bromo-3-fluoro-2-iodobenzene (75g, 249.3mmol) and (5-chloro-2-methoxyphenyl) boronic acid (51.1g, 249.3mmol) were dissolved in 550mL of tetrahydrofuran. To which 2M sodium carbonate (Na) was added₂CO₃) The solution (350mL) and tetrakis (triphenylphosphine) palladium (0) (2.88g, 2.49mmol) were refluxed for 11 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. The aqueous layer was separated and removed, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting mixture was recrystallized using chloroform and ethanol to obtain Compound A-1(63.2g, yield 80%; MS: [ M + H ]]⁺＝314)。

2) Preparation of Compound A-2

Compound A-1(63.2g, 200.3mmol) was dissolved in 750mL of dichloromethane and then cooled to 0 ℃. Boron tribromide (20.0mL, 210.3mmol) was slowly added dropwise, followed by stirring for 12 hours. After completion of the reaction, the reaction mixture was washed three times with water, dried over magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain Compound A-2(57.9g, yield 96%; MS: [ M + H ]]⁺＝300)。

3) Preparation of Compound A-3

Compound A-2(57.9g, 192.0mmol) and calcium carbonate (79.6g, 576.0mol) were dissolved in 350mL of N-methyl-2-pyrrolidone, followed by heating and stirring for 2 hours. After reducing the temperature to room temperatureAfter this time, the reaction mixture was reverse precipitated in water and filtered. The mixture was completely dissolved in methylene chloride, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol and dried to obtain Compound A-3(42.1g, yield 78%; MS: [ M + H ])]⁺＝280)。

4) Preparation of Compound A-4

After dissolving compound A-3(42.1g, 149.5mmol) in tetrahydrofuran (330mL), the temperature was lowered to-78 deg.C and 2.5M t-butyllithium (t-BuLi) (60.4mL, 151.0mmol) was added slowly. The mixture was stirred at the same temperature for 1 hour, and then triisopropyl borate (51.8mL, 224.3mmol) was added thereto, and stirred for 3 hours while gradually raising the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid (300mL) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ether, and then dried in vacuo to obtain Compound A-4(34.3g, yield 93%; MS: [ M + H ]]⁺＝247)。

Preparation examples 1 to 2: synthesis of intermediate Compound B-5

1) Preparation of Compound B-1

After 1-bromo-3-fluoro-2-methoxybenzene (100.0g, 451.5mmol) was dissolved in tetrahydrofuran (1000mL), the temperature was lowered to-78 ℃ and 2.5M tert-butyllithium (t-BuLi) (182.4mL, 456.0mmol) was slowly added dropwise. The mixture was stirred at the same temperature for 1 hour, and triisopropyl borate (B (OiPr) was added thereto₃) (156.3mL, 677.3mmol) and stirred for 3 hours while gradually increasing the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid (150mL) and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and diethyl ether in that order, and then dried in vacuo. After drying, it was recrystallized from chloroform and ethyl acetate and dried to give Compound B-1(84.2g, yield 90%; MS: [ M + H ]]⁺＝230)。

2) Preparation of Compound B-2

Compound B-2(74.6g, yield 52%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-1 of preparation example 1]⁺With the exception that compound B-1(84.2g, 451.7mmol) was used in place of (5-chloro-2-methoxyphenyl) boronic acid.

3) Preparation of Compound B-3

Compound B-3(60.3g, yield 85%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-2]⁺300) except that compound B-2(74.6g, 236.4mmol) was used instead of compound a-1.

4) Preparation of Compound B-4

Compound B-4(48.1g, yield 85%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-3]⁺280) except that compound B-3(60.3g, 199.9mmol) was used instead of compound a-2.

5) Preparation of Compound B-5

Compound B-5(40.1g, yield 95%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-4]⁺247) except that compound B-3(48.1g, 170.9mmol) was used instead of compound a-3.

Preparation examples 1 to 3: synthesis of intermediate Compound C-4

1) Preparation of Compound C-1

Compound C-1(60.1g, yield 76%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-1 of preparation example 1]⁺With the exception that (4-chloro-2-methoxyphenyl) boronic acid (51.1g, 249.3mmol) was used instead of (5-chloro-2-methoxyphenyl) boronic acid (314).

2) Preparation of Compound C-2

Compound C-2(54.0g, yield 94%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-2]⁺300) except that compound C-1(60.1g, 190.4mmol) was used instead of compound a-1.

3) Preparation of Compound C-3

Compound C-4(42.2g, yield 83%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-3]⁺280) except that compound C-2(54.0g, 179.1mmol) was used instead of compound a-2.

4) Preparation of Compound C-4

Compound C-4(34.1g, yield 92%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-4]⁺247) except that compound C-3(42.2g, 170.9mmol) was used instead of compound a-3.

Preparation examples 1 to 4: synthesis of intermediate Compound D-4

1) Preparation of Compound D-1

Compound D-1(63.5g, yield 81%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-1 of preparation example 1]⁺With the exception that (2-chloro-6-methoxyphenyl) boronic acid (51.1g, 249.3mmol) was used instead of (5-chloro-2-methoxyphenyl) boronic acid (314).

2) Preparation of Compound D-2

Compound D-2(55.1g, yield 91%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-2]⁺300) except that compound D-1(63.5g, 201.2mmol) was used instead of compound a-1.

3) Preparation of Compound C-3

Compound C-3(42.0g, yield 82%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-3]⁺280) except that compound C-2(55.1g, 182.7mmol) was used instead of compound a-2.

4) Preparation of Compound C-4

Compound C-4(35.7g, yield 85%; MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-4]⁺247) except that compound C-3(42.0g, 149.2mmol) was used instead of compound a-3.

Preparation example 2

Preparation example 2-1: synthesis of intermediate Compound A-6

1) Preparation of Compound A-5

In a 500mL round-bottom flask, under a nitrogen atmosphere, compound A-4(20.0g, 61mmol) and 2-chloro-4, 6-diphenyltriazine (16.3g, 61mmol) were dissolved in 200mL of tetrahydrofuran. Then, 1.5M or potassium carbonate aqueous solution (100mL) and tetrakis (triphenylphosphine) palladium (0.93g, 1.8mmol) were added thereto, followed by stirring while heating for 7 hours. The temperature of the mixture was lowered to room temperature, and the aqueous layer was separated and removed, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting material was recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate and dried to give Compound A-5(20.5g, yield 78%, MS: [ M + H ]]⁺＝434)。

2) Preparation of Compound A-6

Compound A-5(20.5g, 47mmol), bis (pinacolato) diboron (13.2g, 52mmol) and potassium acetate (16.2g, 165mmol) were mixed and added to 250ml of bis under a nitrogen atmosphere

In an alkane and heated while stirring. Bis (dibenzylideneacetone) palladium (0.81g, 1mmol) and tricyclohexylphosphine (0.8g, 2mmol) were added thereto under reflux and stirred for 13 hours while heating. After completion of the reaction, the reaction solution was cooled to room temperature and then filtered. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The resulting material was distilled under reduced pressure and recrystallized from ethyl acetate to give compound a-6(20.7g, 83%).

Preparation examples 2 to 2: synthesis of intermediate Compound A-8

1) Preparation of Compound A-7

Compound A-7 (17) was prepared in the same manner as in the preparation of Compound A-53g, yield 86%, MS: [ M + H ]]⁺584) except that 2-chloro-4-phenyl-6- (triphenylene-2) -1,3, 5-triazine is used instead of 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound A-8

Compound A-8(16.9g, yield 84%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺676) except that compound a-7 was used instead of compound a-5.

Preparation examples 2 to 3: synthesis of intermediate Compound A-10

1) Preparation of Compound A-9

Compound A-9(15.1g, yield 82%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺599) with the difference that 2- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) 9-phenyl-9H-carbazole is used instead of 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound A-10

Compound A-10(14.5g, yield 83%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺691) except that compound a-9 was used instead of compound a-5.

Preparation examples 2 to 4: synthesis of intermediate Compound A-12

1) Preparation of Compound A-11

Compound A-11(18.4g, yield 82%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺599) with the difference that 9- (3- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) phenyl) 9H-carbazole is used instead of 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound A-12

Compound A-12(17.7g, yield 83%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺691) except that compound a-11 was used instead of compound a-5.

Preparation examples 2 to 5: synthesis of intermediate Compound A-14

1) Preparation of Compound A-13

Compound A-13(16.8g, yield 82%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺523) except that 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole was used instead of 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound A-14

Compound A-14(16.3g, yield 82%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺615) except that compound a-13 was used instead of compound a-5.

Preparation examples 2 to 6: synthesis of intermediate Compound A-16

1) Preparation of Compound A-15

Compound A-14(16.0g, yield 85%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺540) except that 2-chloro-4- (dibenzothiophen-4-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound A-16

Compound A-16(15.6g, yield 86%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺632) except that compound a-15 was used instead of compound a-5.

Preparation examples 2 to 7: synthesis of intermediate Compound A-18

1) Preparation of Compound A-17

Compound A-17(14.2g, yield 77%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺510) with the difference that 2- ([1,1' -biphenyl) is used]-3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine instead of 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound A-18

Compound A-18(13.9g, yield 83%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺602) except that compound a-17 was used instead of compound a-5.

Preparation example 3-1: synthesis of intermediate Compound B-7

1) Preparation of Compound B-6

Compound B-6(14.2g, yield 82%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺434) except that compound B-5 was used instead of compound a-4.

2) Preparation of Compound B-7

Compound B-7(15.0g, yield 82%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺526) except that compound B-6 was used instead of compound a-5.

Preparation examples 3 to 2: synthesis of intermediate Compound B-9

1) Preparation of Compound B-8

Compound B-8(17.5g, yield 80%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺510) with the difference that compound B-5 and 2- ([1,1' -biphenyl) were used]-3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound B-9

With compound A-6Compound B-9(16.2g, yield 78%, MS: [ M + H ]]⁺602) except that compound B-8 was used instead of compound a-5.

Preparation examples 3 to 3: synthesis of intermediate Compound B-11

1) Preparation of Compound B-10

Compound B-10(15.0g, yield 79%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺524) except that compound B-5 and 2-chloro-4- (dibenzofuran-4-yl) -6-phenyl-1, 3, 5-triazine are used instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound B-11

Compound B-11(14.1g, yield 80%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺616) except that compound B-10 was used instead of compound a-5.

Preparation examples 3 to 4: synthesis of intermediate Compound B-13

1) Preparation of Compound B-12

Compound B-12(19.5g, yield 86%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺584) except that compound B-5 and 2-chloro-4-phenyl-6- (triphenylene-2) -1,3, 5-triazine are used instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound B-13

Compound B-13(20.1g, yield 89%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺676) except that compound B-12 was used instead of compound a-5.

Preparation examples 3 to 5: synthesis of intermediate Compound B-15

1) Preparation of Compound B-14

Compound B-14(14.4g, yield 76%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺523) except that compound B-5 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole were used instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound B-15

Compound B-15(12.2g, yield 72%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺615) except that compound B-14 was used instead of compound a-5.

Preparation examples 3 to 6: synthesis of intermediate Compound B-17

1) Preparation of Compound B-16

Compound B-16(16.2g, yield 76%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺With the difference that compound B-5 and 3- (4-chloro-6- (3-dibenzothiophen-4-yl) phenyl) -6-phenyl-1, 3, 5-triazine are used instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound B-17

Compound B-17(14.7g, yield 79%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺708) except that compound B-15 was used instead of compound a-5.

Preparation example 4-1: synthesis of intermediate Compound C-6

1) Preparation of Compound C-5

Compound C-5(13.0g, yield 77%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺434) except that compound C-4 was used instead of compound a-4.

2) Preparation of Compound C-6

Compound C-6(12.8g, yield 82%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺526) except that compound C-5 was used instead of compound a-5.

Preparation example 4-2: synthesis of intermediate Compound C-8

1) Preparation of Compound C-7

Compound C-7(14.0g, yield 76%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺510) with the difference that the compounds C-4 and 2- ([1,1' -biphenyl) are used]-3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound C-8

Compound C-8(12.2g, yield 74%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺602) except that compound C-7 was used instead of compound a-5.

Preparation examples 4 to 3: synthesis of intermediate Compound C-10

1) Preparation of Compound C-9

Compound C-9(16.6g, yield 82%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺584) except that compound C-4 and 2-chloro-4-phenyl-6- (triphenylene-2) -1,3, 5-triazine are used instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound C-10

Compound C-10(16.5g, yield 85%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺676) except that compounding is usedCompound C-9 replaces compound A-5.

Preparation examples 4 to 4: synthesis of intermediate Compound C-12

1) Preparation of Compound C-11

Compound C-11(11.9g, yield 76%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺523) except that instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine, compound C-4 and 9- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) -9H-carbazole were used.

2) Preparation of Compound C-12

Compound C-12(10.8g, yield 77%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺615) except that compound C-11 was used instead of compound a-5.

Preparation examples 4 to 5: synthesis of intermediate Compound C-14

1) Preparation of Compound C-13

Compound C-13(13.6g, yield 77%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺599) with the difference that instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine, compound C-4 and 9- (3- (4-chloro-6-phenyl-1, 3, 5-triazin-2-yl) phenyl) 9H-carbazole are used.

2) Preparation of Compound C-14

Compound C-14(11.8g, yield 75%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺691) except that compound C-11 was used instead of compound a-5.

Preparation examples 4 to 6: synthesis of intermediate Compound C-16

1) Preparation of Compound C-15

Compound C-15(12.1g, yield 74%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺524) except that instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine, compound C-4 and 2-chloro-4- (dibenzofuran-4-yl) -6-phenyl-1, 3, 5-triazine are used.

2) Preparation of Compound C-16

Compound C-16(12.5g, yield 73%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺616) except that compound C-15 was used instead of compound a-5.

Preparation example 5-1: synthesis of intermediate Compound D-6

1) Preparation of Compound D-5

Compound D-5(10.6g, yield 76%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺510) with the difference that the compounds D-4 and 2- ([1,1' -biphenyl) are used]-3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine instead of compound a-4 and 2-chloro-4, 6-diphenyltriazine.

2) Preparation of Compound D-6

Compound D-6(10.0g, yield 80%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺602) except that compound D-5 was used instead of compound a-5.

Preparation examples 5 to 2: synthesis of intermediate Compound D-8

1) Preparation of Compound D-7

Compound D-7(12.7g, yield 77%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-5]⁺599) with the difference that instead of compounds a-4 and 2-Chloro-4, 6-diphenyltriazine.

2) Preparation of Compound D-8

Compound D-8(11.3g, yield 77%, MS: [ M + H ] was prepared in the same manner as in the preparation of Compound A-6]⁺691) except that compound D-7 was used instead of compound a-5.