阅读说明：本技术 多环化合物及包含其的有机发光二极管 (Polycyclic compound and organic light emitting diode comprising same ) 是由 郑珉祐 朴瑟灿 李东勋 张焚在 李征夏 韩修进 于 2019-02-19 设计创作，主要内容包括：本说明书提供化学式1的化合物及包含其的有机发光装置。(The present specification provides a compound of chemical formula 1 and an organic light emitting device including the same.)

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

l1 to L3, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

x1 to X3, which are the same or different from each other, are each independently N or C (R1), 2 or more are N,

w, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

y is O, S, N (R2), C (R3) (R4), or C (R5) bound to L1 or L2,

q1 to Q8, which are identical to or different from each other, are each independently N, C (R6) or C in combination with L1 or L2,

r1 to R6 are the same as or different from each other and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

m is 1 or 2, and when m is 2, the substituents in parentheses are the same or different from each other,

n is an integer of 1 to 5, and when n is 2 or more, the substituents in parentheses are the same or different from each other.

2. The compound of claim 1, wherein said Y is O, S, C (R3) (R4), or C (R5) bound to L1 or L2,

the R3 to R5 are the same as defined in chemical formula 1.

3. The compound of claim 1, wherein Ar1 and Ar2, equal to or different from each other, are each independently an aryl group of 6 to 60 carbon atoms.

4. The compound of claim 1, wherein said X1-X3 is N.

5. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2 or 3:

chemical formula 2

Chemical formula 3

In the chemical formulae 2 and 3,

x1 to X3, Ar1, Ar2, L1 to L3, R5, W, Y, and Q1 to Q8 are the same as defined in chemical formula 1.

6. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:

7. an organic light emitting device comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprise the compound according to any one of claims 1 to 6.

8. The organic light-emitting device according to claim 7, wherein the organic layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.

9. The organic light-emitting device according to claim 7, wherein the organic layer comprises an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer comprises the compound.

10. The organic light-emitting device according to claim 7, wherein the organic layer comprises a light-emitting layer containing the compound.

Technical Field

The present specification claims priority to korean patent application No. 10-2018-0022067, which was filed on 23.2.2018 from the korean patent office, the entire contents of which are incorporated herein.

The present specification relates to a compound and an organic light emitting device including the same.

Background

In this specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between an electrode and the organic semiconductor material. Organic light emitting devices can be broadly classified into the following two types according to the operation principle. The first type is a light-emitting device in which an exciton (exiton) is formed in an organic layer by a photon flowing from an external light source into the device, the exciton is separated into an electron and a hole, and the electron and the hole are transferred to different electrodes to be used as a current source (voltage source). The second type is a light-emitting device in which holes and/or electrons are injected into an organic semiconductor material layer forming an interface with an electrode by applying a voltage or current to 2 or more electrodes, and the light-emitting device operates by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron inhibiting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state. Such an organic light emitting device is known to have characteristics of self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and the like.

Materials used as the organic layer in the organic light emitting device may be classified into a light emitting material, a charge transporting material, such as a hole injecting material, a hole transporting material, an electron suppressing material, an electron transporting material, an electron injecting material, and the like, according to functions. The light-emitting materials include blue, green, and red light-emitting materials, and yellow and orange light-emitting materials required for realizing a more natural color, depending on the light-emitting color.

In addition, as a light emitting material, a host/dopant system may be used for the purpose of increasing color purity and increasing light emitting efficiency by energy transfer. The principle is that when a small amount of a dopant having a smaller energy band gap and excellent light emission efficiency than a host mainly constituting a light emitting layer is mixed in the light emitting layer, excitons generated in the host are transferred to the dopant to emit light with high efficiency. In this case, since the wavelength of the host is shifted to the wavelength range of the dopant, light having a desired wavelength can be obtained according to the kind of the dopant used.

In order to fully utilize the excellent characteristics of the organic light-emitting devices, materials constituting the organic material layers in the devices, such as hole-injecting materials, hole-transporting materials, light-emitting materials, electron-suppressing materials, electron-transporting materials, and electron-injecting materials, are based on stable and effective materials, and development of new materials is continuously required.

Disclosure of Invention

Technical subject

The present specification describes a compound and an organic light-emitting device including the same.

Means for solving the problems

One embodiment of the present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-described chemical formula 1,

l1 to L3, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

x1 to X3, which are the same or different from each other, are each independently N or C (R1), 2 or more are N,

w, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

y is O, S, N (R2), C (R3) (R4), or C (R5) bound to L1 or L2,

q1 to Q8, which are identical to or different from each other, are each independently N, C (R6) or C in combination with L1 or L2,

r1 to R6 are the same as or different from each other and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

m is 1 or 2, and when m is 2, the substituents in parentheses are the same or different from each other,

n is an integer of 1 to 5, and when n is 2 or more, the substituents in parentheses are the same or different from each other.

In addition, the present invention provides an organic light emitting device, comprising: the organic light-emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include the compound.

Effects of the invention

The compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. In the case of manufacturing an organic light-emitting device including at least one compound according to at least one embodiment, an organic light-emitting device having a low driving voltage, high efficiency, and a long lifetime can be obtained.

Drawings

Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 100, an anode 101, a light-emitting layer 102, and a cathode 103.

Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 100, an anode 101, a hole injection layer 104, a hole transport layer 105, an electron suppression layer 106, a light-emitting layer 102, an electron transport layer 107, an electron injection layer 108, and a cathode 103.

100: substrate

101: anode

102: luminescent layer

103: cathode electrode

104: hole injection layer

105: hole transport layer

106: electron inhibiting layer

107: electron transport layer

108: an electron injection layer.

Detailed Description

The present specification will be described in more detail below.

The present specification provides a compound represented by the following chemical formula 1. In the case where the compound represented by the following chemical formula 1 is used for an organic layer of an organic light emitting device, the efficiency and lifetime characteristics of the organic light emitting device are improved.

[ chemical formula 1]

In the above-described chemical formula 1,

l1 to L3, which are identical to or different from one another, are each independently a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

x1 to X3, which are the same or different from each other, are each independently N or C (R1), 2 or more are N,

w, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

y is O, S, N (R2), C (R3) (R4), or C (R5) bound to L1 or L2,

q1 to Q8, which are identical to or different from each other, are each independently N, C (R6) or C in combination with L1 or L2,

r1 to R6 are the same as or different from each other and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

m is 1 or 2, and when m is 2, the substituents in parentheses are the same or different from each other,

n is an integer of 1 to 5, and when n is 2 or more, the substituents in parentheses are the same or different from each other.

In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.

In the present specification, when a member is referred to as being "on" another member, it includes not only a case where the member is in contact with the another member but also a case where the another member is present between the two members.

In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.

The term "substituted or unsubstituted" in the present specification means that the substituent is substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

Examples of the above-mentioned substituent are described below, but the substituent is not limited thereto.

In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), and iodine (I).

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

In the ester group, in the present specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be represented by the following structural formula, 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 compound may have the following structure, but is not limited thereto.

In the context of the present specification,the silyl group may be represented by-SiY₁Y₂Y₃The above-mentioned chemical formula is Y₁、Y₂And Y₃May each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are 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, and a phenylsilyl group.

In this specification, the boron group may be represented BY-BY₄Y₅The above-mentioned chemical formula is Y₄And Y₅May each be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The boron group is not limited to, but specifically, a dimethylboron group, a diethylboron group, a tert-butylmethylboron group, a diphenylboron group, a phenylboron group, and the like.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, and n-octyl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and 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 another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group orA polycyclic aromatic 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. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,Examples of the group include, but are not limited to, a fluorenyl group, a triphenylene group, and the like.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.

In the case where the above-mentioned fluorenyl group is substituted, it may beIsospirofluorene group;(9, 9-dimethylfluorenyl group) andand substituted fluorenyl groups such as (9, 9-diphenylfluorenyl) and the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a cyclic group containing at least 1 of N, O, P, S, Si and Se as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuryl, benzonaphthothienyl, indenocarbazolyl and the like.

In the present specification, the heteroaryl group may be an aromatic group, and the above description of the heterocyclic group may be applied.

In the present specification, an "adjacent" group means a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest to the substituent in terms of a steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.

In the present specification, the aryl group can be applied to the above description of the aryl group, except that the arylene group has a valence of 2.

In the present specification, the heteroaryl group may be substituted with the heteroaryl group except for having a valence of 2.

In an embodiment of the present invention, the X1 to X3 are the same or different and are each independently N or C (R1), and 2 or more are N.

According to another embodiment, X1 through X3 are N.

According to an embodiment of the present invention, Y may be O, S, N (R2), C (R3) (R4), or C (R5) combined with L1 or L2.

When Y is C (R5) bonded to L1 or L2, C is bonded directly to L1 or L2, and the following structure is specifically shown.

According to another embodiment, the Y is O, S, C (R3) (R4) or C (R5) bound to L1 or L2, and the R3 to R5 are as defined in chemical formula 1.

According to an embodiment of the present invention, the chemical formula 1 may be represented by the following chemical formula 2 or 3.

[ chemical formula 2]

[ chemical formula 3]

In the chemical formulae 2 and 3,

x1 to X3, Ar1, Ar2, L1 to L3, R5, W, Y, and Q1 to Q8 are the same as defined in chemical formula 1.

In an embodiment of the present invention, Q1 to Q8 are the same or different from each other, and are each independently N, C (R6) or C combined with L1 or L2.

According to an embodiment of the present invention, R1 to R6 are the same or different and each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to another embodiment, R1 to R6 which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, R1 to R6 which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a silyl group, a boron group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another embodiment, R1 to R6 which are the same as or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another embodiment, R1 mentioned above is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another embodiment, R1 represents hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

According to an embodiment of the present invention, R2 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to another embodiment, R2 mentioned above is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In another embodiment, R2 represents hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another embodiment, R2 is an aryl group having 6 to 60 carbon atoms.

In another embodiment, R2 is hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, or a substituted or unsubstituted phenanthryl group.

According to another embodiment, R2 is hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthryl or phenanthryl.

In another embodiment, R2 is phenyl.

According to an embodiment of the present invention, R3 and R4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another embodiment, R3 and R4, which may be the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, R3 and R4 are the same or different and each independently hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to another embodiment, R3 and R4 are the same as or different from each other and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In another embodiment, R3 and R4 are the same as or different from each other and each independently represents an alkyl group having 1 to 30 carbon atoms.

In another embodiment, R3 and R4 are the same as or different from each other and are each independently a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, or a substituted or unsubstituted butyl group.

According to another embodiment, the above R3 and R4 are methyl.

According to an embodiment of the present invention, R5 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another embodiment, R5 represents hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present invention, R6 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In another embodiment, R6 represents hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms.

According to another embodiment, R6 is hydrogen.

According to an embodiment of the present invention, L1 to L3 are the same or different and each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

According to another embodiment, the above L1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In another embodiment, L1 to L3 which may be the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

According to another embodiment, the above L1 to L3, which are the same or different from each other, are each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In another embodiment, L1 to L3 are the same or different and each independently a direct bond or an arylene group having 6 to 30 carbon atoms.

According to another embodiment, the above L1 to L3, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

In another embodiment, L1 to L3 are the same or different from each other and are each independently a direct bond, phenylene, biphenylene, or terphenylene.

According to another embodiment, the above L1 to L3, which are the same or different from each other, are each independently a direct bond or a phenylene group.

According to an embodiment of the present invention, W is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another embodiment, W is an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 60 carbon atoms which is unsubstituted or substituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In another embodiment, W is an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms which is unsubstituted or substituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to another embodiment, W is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, or a substituted or unsubstituted indenocarbazolyl group.

In another embodiment, W is phenyl substituted or unsubstituted with cyano, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a terphenyl group substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; naphthyl substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a triphenylene group which is substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; phenanthryl substituted or unsubstituted with cyano, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a fluorenyl group which is substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a dibenzofuranyl group which is substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; dibenzothienyl substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; carbazolyl which is unsubstituted or substituted with cyano group, halogen group, alkyl group having 1 to 20 carbon atoms, or aryl group having 6 to 30 carbon atoms; a pyridyl group which is substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a quinolyl group which is substituted or unsubstituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or indenocarbazolyl substituted or unsubstituted with cyano, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to another embodiment, W is phenyl substituted or unsubstituted with cyano, fluoro, methyl, or phenyl; biphenyl substituted or unsubstituted with cyano, fluoro, methyl or phenyl; terphenyl optionally substituted with cyano, fluoro, methyl or phenyl; naphthyl substituted or unsubstituted by cyano, fluoro, methyl or phenyl; triphenylene substituted or unsubstituted with cyano, fluoro, methyl, or phenyl; phenanthryl substituted or unsubstituted with cyano, fluoro, methyl or phenyl; fluorenyl substituted or unsubstituted with cyano, fluoro, methyl or phenyl; dibenzofuranyl substituted or unsubstituted by cyano, fluoro, methyl or phenyl; dibenzothienyl substituted or unsubstituted with cyano, fluoro, methyl or phenyl; carbazolyl substituted or unsubstituted with cyano, fluoro, methyl or phenyl; pyridyl unsubstituted or substituted by cyano, fluoro, methyl or phenyl; quinolinyl substituted or unsubstituted with cyano, fluoro, methyl or phenyl; or indenocarbazolyl, unsubstituted or substituted with cyano, fluoro, methyl, or phenyl.

According to another embodiment, W is phenyl, biphenyl, terphenyl, naphthyl, triphenylene, phenanthryl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, substituted or unsubstituted with fluorine or cyanoCarbazolyl substituted or unsubstituted with phenyl, pyridyl substituted or unsubstituted with phenyl, quinolinyl, or indenocarbazolyl substituted with methyl.

According to an embodiment of the present invention, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another embodiment, Ar1 and Ar2, which are the same or different from each other, are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Ar1 and Ar2 are the same as or different from each other and each independently an aryl group having 6 to 60 carbon atoms.

According to another embodiment, Ar1 and Ar2 are the same as or different from each other, and each is independently an aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar1 and Ar2 are the same as or different from each other and each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthryl group, or a substituted or unsubstituted triphenylene group.

According to another embodiment, Ar1 and Ar2 are the same as or different from each other and are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracenyl, or triphenylenyl.

In another embodiment, Ar1 and Ar2 are the same or different from each other and are each independently phenyl or biphenyl.

In another embodiment, Ar1 and Ar2 are phenyl.

According to another embodiment, any one of Ar1 and Ar2 described above is phenyl and the remaining one is biphenyl.

According to an embodiment of the present specification, m is 1.

According to another embodiment, n is an integer of 1 to 3.

In another embodiment, n is 1 or 2.

According to an embodiment of the present invention, the chemical formula 1 may be represented by any one of the following compounds.

The conjugation length of the compound has a close relationship with the energy band gap. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above. In the present invention, the HOMO and LUMO levels of the compound can also be adjusted by introducing various substituents into the core structure having the above structure.

Further, by introducing various substituents into the core structure having the above-described structure, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, an electron suppression material, a light-emitting layer material, and an electron transport layer material, which are used in the production of an organic light-emitting device, into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

In addition, an organic light-emitting device according to the present invention includes: a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound represented by chemical formula 1.

The organic light-emitting device of the present invention can be manufactured by a method and a material for manufacturing a general organic light-emitting device, in addition to forming one or more organic layers using the above-described compound.

The organic layer can be formed by using the above compound not only by a vacuum deposition method but also by a solution coating method in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic 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 layer that simultaneously performs hole transport and hole injection, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, a hole suppression layer, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto, and a smaller number or a larger number of organic layers may be included.

In the organic light emitting device of the present invention, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound.

In the organic light-emitting device of the present invention, the organic layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include the compound. In this case, the hole injection layer or the hole transport layer may be composed of only the above-mentioned compound, but the above-mentioned compound may be present in a state of being mixed or doped with another hole injection layer or hole transport layer material known in the art.

In the organic light-emitting device of the present invention, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the compound as a dopant of the light emitting layer.

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a dopant of the light-emitting layer, and may further include a host.

The light emitting layer includes a host and a dopant, and the dopant may be included in an amount of 1 to 40 wt%, 1 to 20 wt%, with respect to the total weight of the light emitting layer.

In another embodiment, the organic layer includes a light-emitting layer, the light-emitting layer includes the compound, and further includes a fluorescent host or a phosphorescent host, and may include another organic compound, a metal, or a metal compound as a dopant. At this time, the compound may be included by 20 to 60 wt% with respect to the total weight of the light emitting layer, the host may be included by 20 to 60 wt% with respect to the total weight of the light emitting layer, and the dopant may be included by 1 to 20 wt% with respect to the total weight of the light emitting layer.

As another example, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a dopant of the light-emitting layer, and further includes a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.

According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the compound as a host of the light emitting layer.

As another example, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound as a host of the light-emitting layer and may further include a dopant.

In the organic light-emitting device of the present invention, the organic layer may include an electron-inhibiting layer, and the electron-inhibiting layer may include the compound.

In one embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.

In another embodiment, the first electrode is a cathode and the second electrode is an anode.

The organic light-emitting device may have a stacked structure as described below, for example, but is not limited thereto.

(1) Anode/hole transport layer/light emitting layer/cathode

(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/luminescent layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron inhibiting layer/light emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron inhibiting layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/cathode

(15) Anode/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/electron injection layer/cathode

(16) Anode/hole injection layer/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/cathode

(17) Anode/hole injection layer/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/electron injection layer/cathode

The structure of the organic light emitting device of the present invention may have the structure shown in fig. 1 and 2, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting device in which an anode 101, a light emitting layer 102, and a cathode 103 are sequentially stacked on a substrate 100. In such a structure, the above compound may be contained in the above light-emitting layer 102.

Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 101, a hole injection layer 104, a hole transport layer 105, an electron suppression layer 106, a light-emitting layer 102, an electron transport layer 107, an electron injection layer 108, and a cathode 103 are stacked in this order on a substrate 100. In such a structure, the compound may be contained in the hole injection layer 104, the hole transport layer 105, the light emitting layer 102, or the electron transport layer 107.

For example, the organic light emitting device according to the present invention may be manufactured as follows: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order.

The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that performs both electron injection and electron transport, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that performs both electron injection and electron transport, a hole suppression layer, and the like, but is not limited thereto and may have a single-layer structure. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, blade coating, screen printing, inkjet printing, thermal transfer printing, or the like, using various polymer materials.

The anode is an electrode for injecting holes, and a substance having a large work function is generally preferable as an anode substance so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention 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); ZnO-Al or SnO₂A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode is used for injecting electronsThe electrode of (2) is preferably a substance having a small work function as a cathode substance in order to easily inject electrons into the organic 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, and alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer that functions to smoothly inject holes from the anode into the light-emitting layer, and the hole injection substance is a substance that can favorably inject holes from the anode at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole injection substance is interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may contain a hole injection or transport material known in the art.

An electron inhibiting layer may be provided between the hole transport layer and the light emitting layer. As the electron-suppressing layer, a material known in the art, such as arylamino-based organic material or carbazole-based organic material, can be used.

The light-emitting layer may emit red, green, yellow-green, or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The luminescent material is a material capable of forming a hole transporting layer andthe electron transport layer is preferably a substance that receives holes and electrons, respectively, and combines them to emit light in the visible light region, and has high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerizedstyryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) isAzole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

As a host material of the light-emitting layer, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, and the likePyrimidine derivatives, etc., but are not limited thereto.

When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent material such as piqir (acac) (bis (1-phenylisoquinoline) acetylacetonate iridium, bis (1-phenylisoquinoline) acetylacetonate iridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium), PtOEP (octaethylporphyrin, platinum octaethylporphyrin), or Alq may be used₃(tris (8-hydroxyquinolino) aluminum), etc., but is not limited thereto. When the light-emitting layer emits green or yellow-green light, ir (ppy) can be used as the light-emitting dopant₃Phosphorescent substances such as fac tris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium, and Alq₃(tris (8-hydroxyquinolino) aluminum, tris (8-hydroxyquinoline)) Aluminum), etc., but is not limited thereto. When the light-emitting layer emits blue light, (4, 6-F) can be used as the light-emitting dopant₂ppy)₂Examples of the fluorescent substance include phosphorescent substances such as Irpic, and fluorescent substances such as spiro-DPVBi, spiro-6P, Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers.

The electron transport layer can play a role in smoothing electron transport. The electron transport material is a material capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃And heterocyclic ring-containing compounds such as organic radical compounds, hydroxyl brass-metal complexes, triazines, and the like, but are not limited thereto.

The electron injection layer can perform a function of smoothing electron injection. As the electron-injecting substance, the following compounds are preferred: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,Oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

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

The hole inhibiting layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as those of the hole injecting layer. Specifically, there areAn oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.

Modes for carrying out the invention

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments described in the present specification may be modified into various forms, and the scope of the present specification should not be construed as being limited to the embodiments described below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.

< Synthesis example >

Intermediate synthesis example 1: production of intermediate Compound P-6

1)

Bromo-3-fluoro-2-iodobenzene (1-bromo-3-fluoro-2-iodobenzene) (100g, 333.5mmol), 5-chloro-2-methoxyphenylboronic acid ((5-chloro-2-methoxyphenylboronic acid) (62.2g, 333.5mmol) were dissolved in 800ml of Tetrahydrofuran (THF). Adding sodium carbonate (N a)₂CO₃)2M solution (500mL), tetrakis (triphenylphosphine) palladium (0) [ Pd (PPh)₃)₄](7.7g, 6.7m mol), refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to normal temperature, and the resultant mixture was extracted 3 times with water and toluene. After separation of the toluene layer, useMagnesium sulfate (magnesium sulfate) was dried, and the filtrate was distilled under reduced pressure to give a mixture, which was recrystallized from chloroform and ethanol 3 times to obtain P-1(53.7g, yield 51%; MS: [ M + H ])]⁺＝314)。

2)

Compound P-1(50.0g, 158.5mmol) was dissolved in dichloromethane (Dichlorometahne) (600ml) and then cooled to 0 ℃. Boron tribromide (boron tribromide) (15.8ml, 166.4mmol) was slowly added dropwise, followed by stirring for 12 hours. After the reaction was completed, the reaction mixture was washed with water 3 times, dried over magnesium sulfate (magnesium sulfate), and the filtered filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound P-2(47.4g, yield 99%; MS: [ M + H ])]⁺＝300)。

3)

Compound P-2(40.0g, 132.7mmol) was dissolved in distilled dimethylformamide (D MF) (400 ml). It was cooled to 0 ℃ and sodium hydride (3.5g, 145.9mmol) was slowly added dropwise thereto. After stirring for 20 minutes, the mixture was stirred at 100 ℃ for 1 hour. After the reaction was completed, the reaction mixture was cooled to normal temperature, and 100ml of Ethanol (Ethanol) was slowly added thereto. The mixture obtained by distilling the above mixture under reduced pressure was recrystallized from chloroform and ethyl acetate to obtain Compound P-3(30.3g, yield 81%; MS: [ M + H ]]⁺＝280)。

4)

After compound P-3(30.0g, 106.6mmol) was dissolved in tetrahydrofuran (300ml), the temperature was lowered to-78 ℃ and 1.7M t-butyllithium (t-BuLi) (62.7ml, 106.6mmol) was added slowly. After stirring at the same temperature for 1 hour, triisopropyl borate was added(B(OiPr)₃) (28.3ml, 213.1mmol), and the mixture was stirred for 3 hours while gradually raising the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid (200ml), and the mixture was stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed with water and ethyl ether in this order, and then dried under vacuum. After drying, the resulting mixture was dispersed in ether, stirred for 2 hours, filtered and dried to obtain Compound P-4(24.4g, yield 93%; MS: [ M + H ]]⁺＝247)。

5)

The compound P-4(20.0g, 81.2mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) (21.8g, 81.2mmol) were dispersed in tetrahydrofuran (250ml), and 2M aqueous potassium carbonate (aq. K) was added₂CO₃) (33.6ml, 243.5m mol), tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added₃)₄](1.9g, 2 mol%) and then refluxed with stirring for 4 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered, and dried to obtain Compound P-5(32.4g, yield 92%; MS: [ M + H ]]⁺＝434)。

6)

Compound P-5(30g, 69.2mmol), bis (pinacolato) diboron (19.3g, 76.1mmol), potassium acetate (potassium acetate) (20.4g, 207.5mmol), tetrakis (triphenylphosphine) palladium (0) [ Pd (PPh)₃)₄](1.6g, 2 mol%) was added to tetrahydrofuran (300ml), and refluxed for 12 hours. After the reaction is finished, cooling to normal temperature, and then carrying out reduced pressure distillation to remove the solvent. This was dissolved in Chloroform (Chloroform), washed with water 3 times, and then the organic layer was separated and dried over Magnesium sulfate (Magnesium sulfate). This was subjected to distillation under reduced pressure to give compound P-6(34.5g, yieldThe rate is 95%; MS: [ M + H]⁺＝526)。

Intermediate synthesis example 2: production of intermediate Compound P-8

1)

The compound P-4(40.0g, 162.3mmol) and 2- ([1,1' -biphenyl were added]-4-yl) -4-chloro-6-phenyl-1,3,5-triazine (2- ([1,1' -biphenyl)](4-yl) -4-chloro-6-phenyl-1,3,5-triazine) (55.8g, 162.3mmol) was dispersed in tetrahydrofuran (500ml), and 2M aqueous potassium carbonate (aq. K) was added₂CO₃) (67.2ml, 486.9mmol), tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added₃)₄](3.8g, 2 mol%) and then refluxed with stirring for 4 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and dried to obtain Compound P-7(73.7g, yield 89%; MS: [ M + H ]]⁺＝510)。

2)

Compound P-7(70.5g, 138.3mmol), bis (pinacolato) diboron (38.6g, 152.13mmol), potassium acetate (potassium acetate) (40.7g, 414.9mmol), tetrakis (triphenylphosphine) palladium (0) [ Pd (PPh)₃)₄](3.2g, 2 mol%) was added to tetrahydrofuran (600ml) and refluxed for 12 hours. After the reaction is finished, cooling to normal temperature, and then carrying out reduced pressure distillation to remove the solvent. This was dissolved in Chloroform (Chloroform), washed with water 3 times, and then the organic layer was separated and dried over Magnesium sulfate (Magnesium sulfate). This was subjected to distillation under reduced pressure to give P-8(75.7g, yield 91%; MS: [ M + H ]]⁺＝602)。

Intermediate synthesis example 3: production of intermediate Compounds A-1 to A-4

1) Production of intermediate A-1

After dispersing compound A-1-1 (3-bromo-5-chlorobenzonitrile), 50.0g, 38.1mmol) and (4-chlorophenyl) boronic acid ((4-chlorophenyl) boronic acid) (36.3g, 232.7mmol) in tetrahydrofuran (500ml), 2M aqueous potassium carbonate solution (aq. K) was added₂CO₃) (116.3ml, 232.6mmol) and tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added₃)₄](8.1g, 3 mol%) and then refluxed with stirring for 5 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and dried to obtain Compound A-1-2(34.3g, yield 62%; MS: [ M + H ]]⁺＝239)。

Compound A-1-2(30g, 126.0mmol), bis (pinacolato) diboron (35.2g, 138.64mmol), potassium acetate (potassium acetate) (37.1g, 378.1mmol), 2.2g (3.8mmol) of palladium dibenzylideneacetone and 2.1g (7.6mmol) of tricyclohexylphosphine were added to the bis (pinacolato) diboronIn an alkane (400ml), refluxed for 12 hours. After the reaction is finished, cooling to normal temperature, and then carrying out reduced pressure distillation to remove the solvent. This was dissolved in Chloroform (Chloroform), washed with water 3 times, and then the organic layer was separated and dried with Magnesium sulfate (Magnesium sulfate). This was subjected to distillation under reduced pressure to give Compound A-1(36.6g, yield 88%; MS: [ M + H ]]⁺＝331)。

2) Production of intermediate A-2

Mixing compound A-1-1 (3-bromo-5-chlorobenzonitrile), 50.0g, 38.1mmol) and dibenzo [ b, d ]]Furan-4-ylboronic acid (dibenzo [ b, d ]]Furan-4-ylboronic acid) (49.3g, 232.7mmol) was dispersed in tetrahydrofuran (500ml), and 2M aqueous potassium carbonate (aq. K) was added₂CO₃) (116.3ml, 232.6mmol) and tetrakis (triphenylphosphine) was added) Palladium [ Pd (PPh)₃)₄](8.1g, 3 mol%) and then refluxed with stirring for 5 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and dried to obtain Compound A-1-3(50.0g, yield 71%; MS: [ M + H ]]⁺＝304)。

Compound A-1-3(30g, 99.0mmol), bis (pinacolato) diboron (27.7g, 108.9mmol), potassium acetate (potassium acetate) (29.1g, 297.0mmol), 1.7g (3.0mmol) of palladium dibenzylideneacetone and 1.7g (5.9mmol) of tricyclohexylphosphine were added to the bis (pinacolato) diboronIn an alkane (400ml), refluxed for 12 hours. After the reaction is finished, the reaction product is cooled to normal temperature and then is distilled under reduced pressure, and the solvent is removed. This was dissolved in Chloroform (Chloroform), washed with water 3 times, and then the organic layer was separated and dried with Magnesium sulfate (Magnesium sulfate). This was subjected to distillation under reduced pressure to give Compound A-2(32.9g, yield 84%; MS: [ M + H ]]⁺＝396)。

3) Production of intermediate A-3

Mixing compound A-1-1 (3-bromo-5-chlorobenzonitrile), 50.0g, 38.1mmol) and dibenzo [ b, d ]]Thien-4-ylboronic acid (dibezo [ b, d ]]thiophene-4-ylboronic acid) (53.1g, 232.7mmol) was dispersed in tetrahydrofuran (500ml), and 2M aqueous potassium carbonate (aq. K) was added₂CO₃) (116.3ml, 232.6mmol) and tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added₃)₄](8.1g, 3 mol%) and then refluxed with stirring for 5 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethyl acetate, filtered and dried to obtain Compound A-1-4(50.0g, yield 68%; MS: [ M + H ]]⁺＝320)。

Compound A-1-4(30g, 99.0mmol), bis (pinacolato) diboron (26.3g, 103.4mmol)Potassium acetate (27.7g, 282.0mmol), 1.6g (2.8mmol) of palladium dibenzylideneacetone and 1.6g (2.8mmol) of tricyclohexylphosphine were added to the bisIn an alkane (400ml), refluxed for 12 hours. After the reaction is finished, cooling to normal temperature, and then carrying out reduced pressure distillation to remove the solvent. This was dissolved in Chloroform (Chloroform), washed with water 3 times, and then the organic layer was separated and dried over Magnesium sulfate (Magnesium sulfate). This was subjected to distillation under reduced pressure to give Compound A-3(31.3g, yield 81%; MS: [ M + H ]]⁺＝412)。

4) Production of intermediate A-4

Compound A-1-1 (3-bromo-5-chlorobenzonitrile), 50.0g, 232.7mmol) and 9H-carbazole (46.7g, 279.2mmol) were put into 300mL of xylene and dissolved, and sodium tert-butoxide (64.3g, 465.3mmol) was added thereto and the temperature was raised. Bis (tri-tert-butylphosphine) palladium (1.2g, 1 mol%) was added, and the mixture was stirred under reflux for 12 hours. At the end of the reaction, the temperature was lowered to normal temperature and the resulting solid was filtered. The solid was dissolved in 700mL of chloroform, washed with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by means of a silica gel column using ethyl acetate and hexane to give pale yellow solid compound A-1-5(70.3g, 70%, MS: [ M + H ]]⁺＝303)。

Compound A-1-5(30g, 99.0mmol), bis (pinacolato) diboron (35.2g, 138.6mmol), potassium acetate (potassium acetate) (37.1g, 378.0mmol), 2.2g (3.8mmol) of palladium dibenzylideneacetone and 2.1g (7.6mmol) of tricyclohexylphosphine were added to the bis (pinacolato) diboronIn an alkane (400ml), refluxed for 12 hours. After the reaction is finished, cooling to normal temperature, then carrying out reduced pressure distillation,the solvent is removed. This was dissolved in Chloroform (Chloroform), washed with water 3 times, and then the organic layer was separated and dried with Magnesium sulfate (Magnesium sulfate). This was subjected to distillation under reduced pressure to give Compound A-4(38.8g, yield 78%; MS: [ M + H ]]⁺＝395)。

Intermediate synthesis example 4: production of intermediate Compound B-6

1) Production of Compound B-1

1-bromo-3-chloro-2-methoxybenzene (100.0g, 451.5mmol) was dissolved in tetrahydrofuran (1000mL), the temperature was lowered to-78 deg.C, and 2.5M t-butyllithium (t-BuLi) (182.4mL, 456.0mmol) was slowly added dropwise. After stirring at the same temperature for 1 hour, triisopropyl borate (B (OiPr)₃) (156.3mL, 677.3mmol), and the mixture was stirred for 3 hours while the temperature was gradually raised 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 ethyl ether (ethyl ether) in this order and dried under vacuum. After drying, it was recrystallized from chloroform and ethyl acetate, and then dried, thereby producing Compound B-1(84.2g, yield 90%; MS: [ M + H ]]⁺＝230)。

2) Production 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 P-1 of intermediate Synthesis example 1, except that Compound B-1(84.2g, 451.7mmol) was used in place of (5-chloro-2-methoxyphenyl) boronic acid]⁺＝314)。

3) Production of Compound B-3

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

4) Production of Compound B-4

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

5) Production of Compound B-5

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

5) Production of Compound B-6

Mixing the compound B-5(20.0g, 81.2mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine [2-chloro-4,6-diphenyl-1,3,5-triazine](21.8g, 81.2mmol) was dispersed in tetrahydrofuran (250ml), and 2M aqueous potassium carbonate (aq. K) was added₂CO₃) (33.6ml, 243.5mmol) and tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added₃)₄](1.9g, 2 mol%) and then refluxed with stirring for 4 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered, and then dried, thereby producing compound B-6(28.5g, yield 81%; MS: [ M + H ]]⁺＝434)。

Intermediate synthesis example 5: production of intermediate Compound C-5

1) Production of Compound C-1

Compound C-1(60.1g, yield 76%; MS: [ M + H ]; (M + H); MS: [ M + H ] was prepared in the same manner as in the preparation of Compound P-1 of intermediate Synthesis example 1, except that (4-chloro-2-methoxyphenyl) boronic acid (51.1g, 249.3mmol) was used in place of (5-chloro-2-methoxyphenyl) boronic acid]⁺＝314)。

2) Production of Compound C-2

Preparation of a Compound C-1(60.1g, 190.4mmol) in place of the Compound P-1Compound P-2 Compound C-2(54.0g, yield 94%; MS: [ M + H ]]⁺＝300)。

3) Production of Compound C-3

Compound C-3(42.2g, yield 83%; MS: [ M + H ]; (M + H); was prepared in the same manner as for the preparation of compound P-3, except that compound C-2(54.0g, 179.1mmol) was used in place of compound P-2]⁺＝280)。

4) Production of Compound C-4

Compound C-4(34.1g, yield 92%; MS: [ M + H ]; (M + H); was prepared in the same manner as for compound P-4 except that compound C-3(42.2g, 170.9mmol) was used in place of compound P-3]⁺＝247)。

5) Production of Compound C-5

Compound C-5(27.1g, yield 88%; MS: [ M + H ]; (M + H); was prepared by the same method as that for preparing compound B-6, except that compound C-4(21.7g, 81.3mmol) was used in place of compound B-5]⁺＝434)。

Intermediate synthesis example 6: production of intermediate Compound D-5

1) Production of Compound D-1

Compound D-1(58g, yield 74%; MS: [ M + H ]; (M + H); preparation of intermediate Synthesis example 1) was prepared in the same manner as for the preparation of Compound P-1, except that 1-bromo-2-fluoro-3-iodobenzene was used in place of 1-bromo-3-fluoro-2-iodobenzene]⁺＝315)。

2) Production of Compound D-2

Compound D-2(49.5g, yield 89%; MS: [ M + H ]; (M + H); was prepared in the same manner as for the preparation of compound P-2, except that compound D-1(58g, 183.8mmol) was used in place of compound P-1]⁺＝300)。

3) Production of Compound D-3

In addition to using the compound D-2(49.5g, 164.2mmol) in place of the compound P-2, the compound P-3 was prepared by a methodCompound D-3(40.6g, yield 88%; MS: [ M + H ] was produced in the same manner]⁺＝280)。

4) Production of Compound D-4

Compound D-4(31.9g, yield 90%; MS: [ M + H ]; (M + H); was prepared by the same method as that for preparing compound P-4, except that compound D-3(40.6g, 144.2mmol) was used in place of compound P-3]⁺＝247)。

5) Production of Compound D-5

Compound D-5(27.1g, yield 88%; MS: [ M + H ]; (M + H); was prepared in the same manner as for compound B-6, except that compound D-4(21.7g, 81.3mmol) was used in place of compound B-5]⁺＝434)。

Intermediate synthesis example 7: production of intermediate E-5

1) Production of Compound E-1

Compound E-1(62.3g, yield 79%; MS: [ M + H ] was prepared in the same manner as for the preparation of intermediate Synthesis example 1 Compound P-1, except that 4-bromo-2-fluoro-1-iodobenzene was used in place of 1-bromo-3-fluoro-2-iodobenzene]⁺＝315)。

2) Production of Compound E-2

Compound E-2(51.7g, yield 87%; MS: [ M + H ]; (M + H); was prepared in the same manner as for compound P-2, except that compound E-1(62.3g, 197.4mmol) was used in place of compound P-1]⁺＝300)。

3) Production of Compound E-3

Compound E-3(41.8g, yield 87%; MS: [ M + H ]; (M + H); was prepared in the same manner as for the preparation of compound P-3, except that compound E-2(51.7g, 171.5mmol) was used in place of compound P-2]⁺＝280)。

4) Production of Compound E-4

Compound E-4(31.2g, yield 85%; MS: [ M + H ]; (M + H); was prepared in the same manner as for compound P-4 except that compound E-3(41.8g, 148.5mmol) was used in place of compound P-3]⁺＝247)。

5) Production of Compound E-5

Compound E-5(21.5g, yield 61%; MS: [ M + H ]; (M + H); was prepared in the same manner as for compound B-6, except that compound E-4(21.7g, 81.3mmol) was used in place of compound B-5]⁺＝434)。

Intermediate synthesis example 8: production of intermediate F-5

1) Production of Compound F-1

Compound F-1(60.8g, yield 77%; MS: [ M + H ] was produced by the same method as that for the production of Compound P-1 of intermediate Synthesis example 1, except that 1-bromo-2-fluoro-3-iodobenzene and (4-chloro-2-methoxyphenyl) boronic acid were used instead of 1-bromo-3-fluoro-2-iodobenzene and (5-chloro-2-methoxyphenyl) boronic acid]⁺＝315)。

2) Production of Compound F-2

Compound F-2(52.0g, yield 90%; MS: [ M + H ]; (M + H); was prepared in the same manner as for compound P-2, except that compound F-1(60.8g, 192.7mmol) was used in place of compound P-1]⁺＝300)。

3) Production of Compound F-3

Compound F-3(42.0g, yield 86%; MS: [ M + H ]; (M + H); was prepared in the same manner as for the preparation of compound P-3, except that compound F-2(52.0g, 172.4mmol) was used in place of compound P-2]⁺＝280)。

4) Production of Compound F-4

Compound F-4(29.8g, yield 81%; MS: [ M + H ]; (M + H); was prepared in the same manner as for compound P-4 except that compound F-3(42.0g, 148.5mmol) was used in place of compound P-3]⁺＝247)。

5) Production of Compound F-5

Compound F-5(27.1g, yield 77%; MS: [ M + H ]; (M + H); was prepared in the same manner as for compound B-6, except that compound F-4(21.7g, 81.3mmol) was used in place of compound B-5]⁺＝434)。

Intermediate synthesis example 9: production of intermediate G-6

1) Production of Compound G-1

Compound G-1(49G, yield 79%; MS: [ M + H ] was prepared by the same method as that for preparing Compound P-1 of intermediate Synthesis example 1, except that 1-bromo-3-chlorobenzene and (2- (methylthio) phenyl) boronic acid were used instead of 1-bromo-3-fluoro-2-iodobenzene and (5-chloro-2-methoxyphenyl) boronic acid]⁺＝235)。

2) Production of Compound G-2

To compound G-1(49.0G, 148.5mmol) was added acetic acid (420mL) under a nitrogen atmosphere, and bromine (13.9mL, 271mmol) was charged and stirred at 65 ℃ for 3 hours. After cooling, water was added to the mixture and the precipitated solid was filtered and washed 3 times with water. The filtered filtrate was recrystallized from acetonitrile and toluene to produce Compound G-2(50.3G, yield 77%; MS: [ M + H ]]⁺＝314)。

3) Production of Compound G-3

To compound G-2(50.3G, 160mmol) was added acetic acid (530mL), 35% hydrogen peroxide (16.4G) was added, and the mixture was stirred at room temperature for 5 hours. Aqueous NaOH was added to the reaction, stirred for 20 minutes, and then ethyl acetate was added to remove the aqueous layer. The resulting mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized from a mixed solution of tetrahydrofuran and ethyl acetate, and dried to obtain the above-mentioned compound G-3(43.2G, yield 87%, MS: [ M + H ]]⁺＝308)。

4) Production of Compound G-4

Compound G-3(43.2G, 160mmol) was added to sulfuric acid (220mL) and stirred at room temperature for 5 hours. Is turned to the reverse directionAqueous NaOH solution was added to the reaction mixture, followed by stirring for 30 minutes, addition of chloroform, layer separation, and washing with water 3 times. Ethyl acetate was added and the aqueous layer was removed. The reaction mixture was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized from a mixed solution of tetrahydrofuran and ethyl acetate, and dried to obtain the above-mentioned compound G-4(30.6G, yield 74%, MS: [ M + H ]]⁺＝296)。

5) Production of Compound G-5

Compound G-5(20.4G, yield 75%; MS: [ M + H ]; (M + H); was prepared by the same method as that for preparing compound P-4, except that compound G-4(42.0G, 148.5mmol) was used in place of compound P-3]⁺＝263)。

6) Production of Compound G-6

The compound G-5(20.0G, 76.3mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine [2-chloro-4,6-diphenyl-1,3,5-triazine](20.4g, 73.3mmol) was dispersed in tetrahydrofuran (250ml), and 2M aqueous potassium carbonate (aq. K) was added₂CO₃) (115ml, 229.0mmol), tetrakis (triphenylphosphine) palladium [ Pd (PPh) was added₃)₄](1.8g, 2 mol%) and then refluxed with stirring for 4 hours. The temperature was reduced to normal temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered, and then dried, thereby producing compound G-6(22.3G, yield 65%; MS: [ M + H ]]⁺＝450)。

< Synthesis of Compound 1 >

Under nitrogen, compound P-5(20.0g, 46.2mmol) and compound A-2(18.2g, 46.2mmol) were added to the mixtureIn an alkane (200mL), stirred and refluxed. Then, potassium carbonate (19.1g, 138.5mmol) was dissolved in water (40mL) and charged and sufficiently stirred, and then bis (tri-tert-butylphosphino) palladium (0) (0.7g, 1.4mmol) was charged. After 9 hours of reaction, the temperature was lowered to normal temperature and filtered. Will filterThe extract was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized from a mixed solution of tetrahydrofuran and ethyl acetate. The resulting solid was filtered and dried to obtain Compound 1(14.5g, yield 47%, MS: [ M + H ]]⁺＝667)。

< Synthesis of Compound 2 >

Compound 2(15.1g, 48%, MS: [ M + H ] was produced in the same manner as in the production of Compound 1, except that Compound A-3 was used in place of Compound A-2]⁺＝683)。

< Synthesis of Compound 3 >

Compound 3(15.7g, 51%, MS: [ M + H ] was produced in the same manner as in the production of Compound 1, except that Compound A-4 was used in place of Compound A-2]⁺＝666)。

< Synthesis of Compound 4 >

Under nitrogen, compound P-7(20.0g, 39.3mmol) and compound A-3(18.2g, 46.2mmol) were added to the mixtureIn an alkane (200mL), stirred and refluxed. Then, potassium carbonate (16.3g, 117.9mmol) was dissolved in water (40mL) and charged and sufficiently stirred, and then bis (tri-tert-butylphosphino) palladium (0) (0.6g, 1.2mmol) was charged. After 12 hours of reaction, the temperature was lowered to normal temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then tetrahydrofuran andand recrystallizing the mixed solution of the ethyl acetate. The resulting solid was filtered and dried to obtain Compound 4(9.8g, yield 33%, MS: [ M + H ]]⁺＝758)。

< Synthesis of Compound 5 >

Compound 5(14.8g, 47%, MS: [ M + H ] was produced in the same manner as for the production of Compound 4, except that Compound B-6 was used in place of Compound P-7]⁺＝683)。

< Synthesis of Compound 6>

Compound 6(9.8g, 31%, MS: [ M + H ] was produced in the same manner as for Compound 4, except that Compound C-5 was used in place of Compound P-7]⁺＝683)。

< Synthesis of Compound 7 >

Compound 7(13.8g, 44%, MS: [ M + H ] was produced in the same manner as for the production of Compound 4, except that Compound D-5 was used in place of Compound P-7]⁺＝683)。

< Synthesis of Compound 8 >

Compound 8(16.4g, 52%, MS: [ M + H ] was produced in the same manner as for Compound 4, except that Compound E-5 was used in place of Compound P-7]⁺＝683)。

< Synthesis of Compound 9 >

Compound 9(21.4g, 68%, MS: [ M + H ] was produced in the same manner as in the production of Compound 4, except that Compound F-5 was used in place of Compound P-7]⁺＝683)。

< Synthesis of Compound 10>

Compound 10(11.5G, 37%, MS: [ M + H ] was produced in the same manner as in the production of Compound 4, except that Compound G-6 was used in place of Compound P-7]⁺＝699)。

< Experimental example >

Experimental example 1.

Indium Tin Oxide (ITO) and a process for producing the sameThe glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared, the following HI-1 compound was addedThe thickness of (3) was subjected to thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following HT-1 compound is addedIs subjected to thermal vacuum evaporation to form a hole transport layer, and an HT-2 compound is deposited on the HT-1 deposited filmThe electron inhibiting layer is formed by vacuum evaporation. On the HT-2 deposited film, the compound 1 produced in the synthesis example, the YGH-1 compound, and the phosphorescent dopant YGD-1 were co-deposited at a weight ratio of 44:44:12 to form a light-emitting layerA thick light emitting layer. On the light-emitting layer, the following ET-1 compound is addedIs formed by vacuum vapor deposition, and on the electron transport layer, the following ET-2 compound and Li are vacuum vapor deposited at a weight ratio of 98:2, thereby formingA thick electron injection layer. On the electron injection layer, toThe cathode is formed by evaporating aluminum to a certain thickness.

In the above process, the evaporation speed of the organic material is maintainedAluminum maintenanceIn the vapor deposition ofWhile, the vacuum degree was maintained at 1 × 10^-7～5×10^-8And (4) supporting.

< Experimental examples 2 to 10>

An organic light-emitting device was produced in the same manner as in experimental example 1, except that in experimental example 1, the compounds described in table 1 below were used instead of compound 1 of synthetic example 1.

< comparative Experimental examples 1 to 6>

An organic light-emitting device was produced in the same manner as in experimental example 1, except that in experimental example 1, the compounds described in table 1 below were used instead of compound 1 of synthetic example 1.

The compounds of CE1 to CE6 of table 1 below are shown below.

In the above experimental examples and comparative experimental examples, the organic light emitting device was set at 10mA/cm²The voltage and efficiency were measured at a current density of 50mA/cm²The lifetime was measured at the current density of (2), and the results are shown in table 1 below. In this case, LT95 represents a time at which the luminance becomes 95% of the initial luminance.

[ Table 1]

As shown in table 1 above, it was confirmed that in the case of experimental examples 1 to 10 using the compound of the present invention as a light emitting layer material, the characteristics of excellent efficiency and lifetime were exhibited as compared with comparative experimental examples 1 to 6. This is because, when a cyano group is further added to the triazine unit together with dibenzofuran or thiophene, the electron transporting unit and the substance are excellent in stability, and the device is excellent in efficiency, life, and the like.