阅读说明：本技术 多环化合物及包含其的有机电子器件 (Polycyclic compound and organic electronic device comprising same ) 是由 琴水井 尹正民 具己洞 李起坤 金明坤 金京嬉 金公谦 李炯珍 于 2019-04-05 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电子器件。(The present specification provides a compound of chemical formula 1 and an organic electronic device comprising 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,

r1 and R2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a silyl group, a boryl group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylalkylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkylheteroarylamino group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

ar1 to Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted hydrocarbon ring group, or a substituted or unsubstituted heterocyclic ring group,

n1 is an integer of 0 to 3, when n1 is 2 or more, 2 or more R1 s are the same or different from each other,

when n2 is an integer of 0 to 5 and n2 is 2 or more, 2 or more R2 s are the same as or different from each other.

2. The compound according to claim 1, wherein the Ar1 to Ar4 are the same as or different from each other, and each is independently a substituted or unsubstituted hydrocarbon ring group having 3 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

3. The compound of claim 1, wherein said Ar1 to Ar4 are the same as or different from each other, and are each independently 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 fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted hydrogenated naphthalene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

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

5. the compound according to claim 1, wherein the maximum luminescence peak of the compound is 430nm to 470 nm.

6. An organic electronic device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to any one of claims 1 to 5.

7. The organic electronic device of claim 6, wherein the organic layer comprises a hole injection layer or a hole transport layer comprising the compound.

8. The organic electronic device of claim 6, wherein the organic layer comprises an electron transport layer or an electron injection layer comprising the compound.

9. The organic electronic device of claim 6, wherein the organic layer comprises a light emitting layer comprising the compound.

10. The organic electronic device according to claim 6, wherein the organic layer comprises a light-emitting layer containing the compound as a dopant of the light-emitting layer.

11. The organic electronic device according to claim 6, wherein the organic electronic device is selected from the group consisting of organic light emitting devices, organic phosphorescent devices, organic solar cells, Organic Photoconductors (OPC) and organic transistors.

12. The organic electronic device according to claim 10, wherein the light emitting layer further comprises the following chemical formula 1-a as a host:

chemical formula 1-A

In the chemical formula 1-a,

a1 to A3, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

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,

r11 is hydrogen, deuterium, a halogen group, cyano, nitro, silyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted phosphinoxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

q1 is an integer of 0 to 7, and when q1 is 2 or more, 2 or more R11 s are the same or different from each other.

13. The organic electronic device according to claim 10, wherein the light emitting layer further comprises 2 or more of the compounds represented by the following chemical formulae 1-B and 1-C as a host:

chemical formula 1-B

Chemical formula 1-C

In the chemical formulas 1-B and 1-C,

a4 to A8, equal to or different from each other, are each independently hydrogen or a substituted or unsubstituted aryl group,

a9 is a substituted or unsubstituted heterocyclic group,

l4 to L9, 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,

r12 and R13, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

q2 and q3 are each an integer of 0 to 7, and when q2 and q3 are each 2 or more, the substituents in parentheses are the same as or different from each other.

Technical Field

The present specification claims priority to korean patent application No. 10-2018-0039760, filed on 5.4.2018 to the korean patent office, the entire contents of which are incorporated herein.

The present description relates to compounds and organic electronic devices comprising the same.

Background

As a representative example of the organic electronic device, there is an organic light emitting device. 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 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 both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exitons) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned to the ground state again.

Most of the substances used in organic light-emitting devices are pure organic substances or complex compounds of organic substances and metals. The materials used in the organic light emitting device may be classified into a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like according to the use. Here, as the hole injecting substance or the hole transporting substance, an organic substance having p-type properties, that is, an organic substance which is easily oxidized and has an electrochemically stable state at the time of oxidation is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having an n-type property, that is, an organic substance which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. The light-emitting layer material is preferably a material having both p-type and n-type properties, that is, a material having a stable form in both an oxidized state and a reduced state, and is preferably a material having high light emission efficiency in converting excitons into light when they are formed.

In order to fully exhibit the excellent characteristics of the organic light-emitting device, development of a substance constituting an organic layer in the device is continuously required.

Disclosure of Invention

Technical subject

The present specification describes compounds and organic electronic devices comprising 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,

r1 and R2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a silyl group, a boryl group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylalkylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkylheteroarylamino group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

ar1 to Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

n1 is an integer of 0 to 3, when n1 is 2 or more, 2 or more R1 s are the same or different from each other,

when n2 is an integer of 0 to 5 and n2 is 2 or more, 2 or more R2 s are the same as or different from each other.

In addition, the present invention provides an organic electronic device, comprising: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound.

Effects of the invention

The compounds described in this specification can be used as materials for organic layers of organic electronic devices. In the case of manufacturing an organic electronic device including the compound according to at least one embodiment, an organic electronic device having high efficiency and long lifetime can be obtained.

Drawings

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

Fig. 2 illustrates an example of an organic light-emitting device composed of 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.

FIG. 3 is a graph showing an MS measurement pattern of the compound BD-2.

FIG. 4 is a graph showing an MS measurement pattern of the compound BD-3.

FIG. 5 is a graph showing an MS measurement pattern of the compound BD-6.

1: substrate

2: anode

3: luminescent layer

4: cathode electrode

5: hole injection layer

6: hole transport layer

7: luminescent layer

8: electron transport 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 electronic device, the structure of a luminophore is simple and rigid, and thus the half width is relatively improved, so that high efficiency can be achieved. In addition, since dibenzofuran is included to be chemically more stable, the life span characteristics of the organic electronic device are improved in the case of manufacturing the organic electronic device including the compound represented by chemical formula 1 of the present invention.

[ chemical formula 1]

In the above-described chemical formula 1,

r1 and R2, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a silyl group, a boryl group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylalkylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkylheteroarylamino group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

ar1 to Ar4, which are the same or different from each other, are each independently hydrogen, deuterium, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

n1 is an integer of 0 to 3, when n1 is 2 or more, 2 or more R1 s are the same or different from each other,

when n2 is an integer of 0 to 5 and n2 is 2 or more, 2 or more R2 s are the same as or different from each other.

In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.

In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the another member but also a case where the other member exists 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.

In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a silyl group, a boryl group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkylamino group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamino group, a substituted or unsubstituted arylalkylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkylheteroarylamino group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent formed by connecting 2 or more substituents among the above-exemplified substituents, or do not have any substituents. 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, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).

In the present specification, the silyl group may be represented by-SiY₁Y₂Y₃The above-mentioned chemical formula is Y₁、Y₂And Y₃Each may 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 Y₅Each may be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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 alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited thereto.

The alkyl group, the alkoxy group, and the substituent including the other alkyl moiety described in the present specification are all included in a linear or branched form.

In the present specification, the aryl group in the aryloxy group can be applied to the aryl group described later.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl and the like.

In the present specification, the number of carbon atoms of the alkylamino group is not particularly limited, but may be 1 to 40, and according to one embodiment, may be 1 to 20. Specific examples of the alkylamino group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, and a diethylamino group.

In the specification, as an example of the arylamine group, there is a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group.

Specific examples of arylamine groups include, but are not limited to, phenylamino groups, naphthylamino groups, biphenylamino groups, anthracylamino groups, diphenylamino groups, phenylnaphthylamino groups, biphenylphenylamino groups, biphenylylamino groups, fluorenylphenylamino groups, and the like.

In the present specification, as examples of the heteroarylamino group, there are a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted triheteroarylamino group. The heteroaryl group in the heteroarylamino group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group containing 2 or more heteroaryls may contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or may contain both a monocyclic heteroaryl group and a polycyclic heteroaryl group.

In the present specification, an arylalkylamino group means an amino group substituted with an aryl group and an alkyl group.

In the present specification, arylheteroarylamino refers to an amino group substituted with an aryl group and a heteroaryl group.

In the present specification, an arylalkylamino group means an amino group substituted with an aryl group and an alkyl group.

In the present specification, alkylheteroarylamino refers to an amino group substituted with an alkyl group and a heteroaryl group.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. 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 or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the carbon atom of the aryl groupThe number is 6 to 20. 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 benzofluorenyl group, and a triphenylene group.

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

Isospirofluorene group; (9, 9-dimethylfluorenyl) andand (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 1 or more of N, O, P, S, Si and Se as heteroatoms, 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, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuryl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuryl and benzonaphthothienyl.

In the present specification, the hydrocarbon ring group may be an aromatic group, an aliphatic group, or a condensed ring of an aromatic group and an aliphatic group, the aromatic hydrocarbon ring may be the aromatic ring except for having a valence of 1, and the aromatic ring may be the aromatic ring except for having a valence of 1, and the aliphatic hydrocarbon ring may be the cycloalkyl ring except for having a valence of 1. Further, the aromatic and aliphatic condensed ringsAs an example of (A), hydrogenated naphthalene, specifically, 1,2,3, 4-tetrahydronaphthalene

In the present specification, the above description of the heterocyclic group can be applied to the heteroaryl group except for the heteroaryl group.

According to an embodiment of the present invention, the maximum light emission peak of the compound of the present invention may be in a range of 430nm to 470nm, and when the compound is included in a light emitting layer of an organic electronic device, blue light is emitted.

According to an embodiment of the present invention, R1 and R2 which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a silyl group, a boryl group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 40 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 heterocyclic group having 2 to 60 carbon atoms.

According to another embodiment, R1 and R2 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 silyl group, a boryl group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 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 heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, R1 and R2 which are the same as or different from each other, are each independently hydrogen, deuterium, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, R1 and R2, which are the same or different from each other, are each independently hydrogen, deuterium, a silyl group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In another embodiment, R1 and R2 are the same as or different from each other and are each independently hydrogen, deuterium, trimethylsilyl, substituted or unsubstituted methyl, substituted or unsubstituted cyclohexyl, or substituted or unsubstituted phenyl.

According to another embodiment, R1 and R2 are the same or different from each other and are each independently hydrogen, deuterium, trimethylsilyl, methyl, cyclohexyl, or phenyl.

According to an embodiment of the present invention, n1 is an integer of 0 to 2.

According to another embodiment, n1 is 0 or 1.

According to an embodiment of the present invention, n2 is an integer of 0 to 2.

According to another embodiment, n2 is 0 or 1.

According to an embodiment of the present invention, Ar1 to Ar4 are the same as or different from each other, and each independently represents hydrogen, deuterium, a silyl group, a boryl group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 3 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In another embodiment, Ar1 to Ar4 which are the same as or different from each other, are each independently hydrogen, deuterium, a silyl group, a boryl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted hydrocarbon ring group having 3 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to another embodiment, Ar1 to Ar4 which are the same as or different from each other, are each independently a substituted or unsubstituted hydrocarbon ring group of 3 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group of 2 to 60 carbon atoms.

In another embodiment, Ar1 to Ar4 which are the same as or different from each other, are each independently a substituted or unsubstituted hydrocarbon ring group having 3 to 30 carbon atoms or a substituted or unsubstituted heterocyclic ring group having 2 to 30 carbon atoms.

According to another embodiment, Ar1 to Ar4 are the same as or different from each other, and each is independently 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 fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted hydrogenated naphthalene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group.

In another embodiment, Ar1 to Ar4 which are the same as or different from each other, are each independently a phenyl group substituted or unsubstituted with a substituent group which is linked by 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a biphenyl group substituted or unsubstituted with 1 or more substituents or 2 or more substituents linked together, the substituents being selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a trisbiphenyl group substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group are bonded; a naphthyl group substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group are bonded to each other; a substituted or unsubstituted fluorenyl group which is substituted with 1 or more substituents or 2 or more substituents bonded to each other and which is selected from the group consisting of deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted benzofluorenyl group which is substituted with 1 or more substituents or 2 or more substituents bonded to each other and which is selected from the group consisting of deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a phenanthryl group substituted or unsubstituted with a substituent group in which 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group are bonded to each other; hydrogenated naphthalene substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other, which are selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; a dibenzofuranyl group substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other, wherein the substituents are selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; or a carbazolyl group substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other, said substituents being selected from the group consisting of deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group.

In another embodiment, Ar1 to Ar4 which are the same as or different from each other, are each independently a phenyl group which is substituted or unsubstituted with a substituent group which is linked by 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other, which is selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a terphenyl group substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other, which is selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; naphthyl substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a fluorenyl group which is substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other and which is selected from the group consisting of deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a benzofluorenyl group which is substituted or unsubstituted by 1 or more substituents or 2 or more substituents bonded to each other and selected from the group consisting of deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a phenanthryl group which is substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other and selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; hydrogenated naphthalene substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other, which are selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; a dibenzofuranyl group which is substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other and which is selected from deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a carbazolyl group substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other, which is selected from the group consisting of deuterium, a halogen group, a silyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, Ar1 to Ar4 are the same as or different from each other, and each is independently a phenyl group which is substituted or unsubstituted with a substituent group which is formed by connecting 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group; a biphenyl group which is substituted or unsubstituted with 1 or more substituents or 2 or more substituents linked to each other and selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group; a terphenyl group substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other and selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group; naphthyl substituted or unsubstituted with 1 or more substituents or 2 or more substituents linked to each other selected from deuterium, a halogen group, cyano, trimethylsilyl, trifluoromethyl, methyl, ethyl, tert-butyl, phenyl, tert-butylphenyl and carbazolyl; a fluorenyl group which is substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other and selected from the group consisting of deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group; a benzofluorenyl group which is substituted or unsubstituted by a substituent group formed by connecting 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group; a phenanthryl group which is unsubstituted or substituted with a substituent group which is linked by 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group; hydrogenated naphthalene substituted or unsubstituted with 1 or more substituents or 2 or more substituents bonded to each other selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group; a dibenzofuranyl group which is unsubstituted or substituted with a substituent group which is linked with 1 or more substituents or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group; or a carbazolyl group which is unsubstituted or substituted with 1 or more substituents or 2 or more substituents linked together and selected from the group consisting of deuterium, a halogen group, a cyano group, a trimethylsilyl group, a trifluoromethyl group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group, a tert-butylphenyl group and a carbazolyl group.

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

The compound of the above chemical formula 1 may be prepared into a core structure through a process as shown in the following reaction formula. The substituents may be bonded by a method known in the art, and the kind, position or number of the substituents may be changed according to a technique known in the art.

< reaction formula >

The above reaction formula is merely an example of a method for producing a core structure of the compound according to an embodiment of the present invention, and a substituent is attached, and is not limited thereto.

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

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

Further, by introducing various substituents into the core structure having the above structure, a compound having the inherent characteristics of the introduced substituent 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, the organic electronic device according to the present invention is characterized by comprising: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the above-mentioned compound.

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

According to an embodiment of the present invention, the above organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an Organic Photoconductor (OPC), and a glass transistor.

The organic light emitting device is exemplified below.

The organic layer can be formed by using the above compound not only by a vacuum evaporation 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 be formed of a single layer structure, or may be formed of 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 which performs both hole injection and hole transport, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer which performs both electron injection and electron transport, and the like as organic layers. However, the structure of the organic light emitting device is not limited thereto, and a smaller or greater number of organic layers may be included.

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

In the organic light emitting device of the present invention, the above organic layer may include a hole injection layer or a hole transport layer, and the above hole injection layer or hole transport layer may contain the above-mentioned compound.

At this time, the hole injection layer or the hole transport layer may be composed of only the above-mentioned compounds, and the above-mentioned compounds may also exist in a state of being mixed or doped in materials of other hole injection layers or hole transport layers known in the art.

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

According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the above-mentioned 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 may further include a host, wherein the light-emitting layer includes the compound as a dopant of the light-emitting layer.

According to 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 the following chemical formula 1-a as a host.

[ chemical formula 1-A ]

In the above chemical formula 1-a,

a1 to A3, which are the same or different from each other, are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

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,

r11 is hydrogen, deuterium, a halogen group, a cyano group (-CN), a nitro group, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

q1 is an integer of 0 to 7, and when q1 is 2 or more, 2 or more R11 s are the same or different from each other.

According to an embodiment of the present invention, a1 to A3 are the same or different and each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

According to another embodiment, a1 through A3 which are the same or different from each other, are each independently hydrogen, 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.

In another embodiment, a1 through A3 which are the same or different from each other, are each independently hydrogen, 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, a3 is hydrogen.

In another embodiment, a1 above is hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thienyl, or substituted or unsubstituted indolocarbazolyl.

According to another embodiment, a1 above is hydrogen; a phenyl group which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; naphthyl substituted or unsubstituted with deuterium, an alkyl group of 1 to 10 carbon atoms, or an aryl group of 6 to 30 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; naphthobenzofuranyl substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; thienyl substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or indolocarbazolyl which is unsubstituted or substituted by deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In another embodiment, a1 is hydrogen, phenyl substituted or unsubstituted with deuterium, naphthyl substituted or unsubstituted with methyl, dibenzofuranyl, naphthobenzofuranyl, thienyl substituted with phenyl, or indolocarbazolyl.

According to an embodiment of the present invention, a2 is hydrogen or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, a2 above is hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

In another embodiment, a2 is hydrogen; a phenyl group which is substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a naphthyl group which is unsubstituted or substituted by deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to another embodiment, a2 above is hydrogen; phenyl substituted or unsubstituted with cyclohexyl, phenyl or naphthyl; biphenyl substituted or unsubstituted with deuterium, fluoro, cyano, or trimethylsilyl; or naphthyl substituted or unsubstituted with methyl, phenyl, or naphthyl.

According to an embodiment of the present invention, 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, or a substituted or unsubstituted heteroarylene group.

In another embodiment, each of L1 to L3 which are the same or different from each other, is 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.

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, 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, or a substituted or unsubstituted naphthylene group.

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 phenylene group, or a naphthylene group.

According to an embodiment of the present invention, R11 is hydrogen, deuterium, a halogen group, a cyano group (-CN), a nitro group, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to another embodiment, R11 mentioned above is hydrogen, deuterium, a halogen group, a cyano group (-CN), a nitro group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted phosphinoxide group, 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, R11 is hydrogen.

According to an embodiment of the present invention, q1 is an integer of 0 to 2.

In another embodiment, q1 is 0 or 1.

In one embodiment of the present specification, the chemical formula 1-a may be represented by any one of the following compounds.

In the case of including the compound of the present invention as a dopant of the light emitting layer and including the above chemical formula 1-a as a host, the content of the dopant may be 1 to 10 parts by weight based on 100 parts by weight of the host.

According to another embodiment, the organic layer includes a light emitting layer, the light emitting layer includes the compound as a dopant of the light emitting layer, and may further include 2 or more of the compounds represented by the following chemical formulas 1-B and 1-C as a host.

[ chemical formula 1-B ]

[ chemical formula 1-C ]

In the above chemical formulas 1-B and 1-C,

a4 to A8, equal to or different from each other, are each independently hydrogen or a substituted or unsubstituted aryl group,

a9 is a substituted or unsubstituted heterocyclic group,

l4 to L9, 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,

r12 and R13, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a nitro group, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

q2 and q3 are each an integer of 0 to 7, and when q2 and q3 are each 2 or more, the substituents in parentheses are the same as or different from each other.

According to an embodiment of the present invention, a4 to A8 are the same or different and each independently hydrogen or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another embodiment, a4 through A8, which may be the same or different from each other, are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, the above a6 and A8 are hydrogen.

In another embodiment, a5 and a7 are the same as or different from each other, and each is independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

In another embodiment, a5 and a7 are the same as or different from each other, and are each independently hydrogen; a phenyl group which is substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or a naphthyl group which is substituted or unsubstituted with deuterium (D), a halogen group, a cyano group, a silyl group, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

According to another embodiment, a5 and a7 are the same as or different from each other, and are each independently hydrogen; phenyl substituted or unsubstituted with cyclohexyl, phenyl or naphthyl; biphenyl substituted or unsubstituted with deuterium, fluoro, cyano, or trimethylsilyl; or naphthyl substituted or unsubstituted with methyl, phenyl, or naphthyl.

According to an embodiment of the present invention, a4 is hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

According to another embodiment, a4 above is hydrogen; a phenyl group which is substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or naphthyl substituted or unsubstituted by deuterium, an alkyl group of a carbon number of 1 to 10, or an aryl group of a carbon number of 6 to 30.

In another embodiment, a4 above is hydrogen, phenyl substituted or unsubstituted with deuterium, or naphthyl substituted or unsubstituted with methyl.

According to one embodiment of the present specification, a9 is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to another embodiment, a9 mentioned above is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, a9 is a substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted thienyl, or substituted or unsubstituted indolocarbazolyl.

According to another embodiment, a9 mentioned above is a dibenzofuranyl group substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; naphthobenzofuranyl substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; thienyl substituted or unsubstituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms; or an indolocarbazolyl group which is unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In another embodiment, a9 is dibenzofuranyl, naphthobenzofuranyl, thienyl substituted with phenyl, or indolocarbazolyl.

According to an embodiment of the present invention, the above L4 to L9, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

In another embodiment, each of L4 to L9 which are the same or different from each other, is 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 L4 to L9, 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.

According to another embodiment, the above L4 to L9, 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, the above L4 to L9, which are the same or different from each other, are each independently a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

According to another embodiment, the above L4 to L9, which are the same or different from each other, are each independently a direct bond, a phenylene group, or a naphthylene group.

According to an embodiment of the present invention, R12 and R13, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a nitro group, a silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to another embodiment, the above R12 and R13, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group (-CN), a nitro group, a silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted phosphine oxide group, 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, the above R12 and R13 are hydrogen.

According to an embodiment of the present disclosure, when q2 is an integer of 0 to 7 and q2 is 2 or more, 2 or more R12 are the same or different from each other.

According to another embodiment, q2 is an integer of 0 to 2.

According to another embodiment, q2 is 0 or 1.

According to an embodiment of the present disclosure, when q3 is an integer of 0 to 7 and q3 is 2 or more, 2 or more R13 are the same or different from each other.

According to another embodiment, q3 is an integer of 0 to 2.

According to another embodiment, q3 is 0 or 1.

In one embodiment of the present specification, the chemical formula 1-B may be represented by any one of the following compounds.

In one embodiment of the present specification, the chemical formula 1-C may be represented by any one of the following compounds.

In the case where the compound of the present invention is contained as a dopant of the light emitting layer and 2 or more of the compounds represented by the above chemical formulas 1-B and 1-C are contained as a host, the content of the dopant may be 1 to 10 parts by weight based on 100 parts by weight of the host.

According to another embodiment, the above compound may be included as a dopant of the light emitting layer, and the compound represented by the above chemical formula 1-B and the compound represented by the above chemical formula 1-C may be included as a host of the light emitting layer, and a mixing weight ratio of the above hosts (1-B:1-C) may be 95:5 to 5: 95.

In another embodiment, the organic layer includes a light emitting layer, the light emitting layer includes the compound as a dopant of the light emitting layer, includes a fluorescent host or a phosphorescent host, and may include other organic compounds, metals, or metal compounds as a dopant.

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, 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 includes a light-emitting layer, and the light-emitting layer includes 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.

For example, the organic light emitting device may have a stacked-layer structure as shown below, 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 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the above-described compound may be contained in the above-described light-emitting layer 3.

Fig. 2 illustrates a structure of an organic light emitting device in which 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 are sequentially stacked on a substrate 1. In the structure described above, the above-described compound may be contained in the above-described hole injection layer 5, hole transport layer 6, light emitting layer 7, or electron transport layer 8.

For example, the organic light emitting device according to the present invention may be manufactured by: the organic el device is manufactured by depositing a metal or 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) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a layer in which hole injection and hole transport are simultaneously performed, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, and a layer in which electron injection and electron transport are simultaneously performed on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.

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, and the like. In addition, the organic layer may be formed using various polymer materials, and a smaller number or a larger number of layers may be formed by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method.

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 an electrode for injecting electrons, and a substance having a small work function is generally preferable 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 (porphyrine), 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 thickness of the hole injection layer may be 1 to 150 nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the hole injection property can be prevented from being lowered, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the driving voltage can be prevented from being increased to increase the movement of holes when the thickness of the hole injection layer is too large.

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 arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present at the same time, but the present invention is not limited thereto, and the hole transport layer may be formed in 1 layer or more in the organic light-emitting device.

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. The electron-suppressing layer may use the above-mentioned compounds or materials known in the art.

The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having 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 (dimerized styryl) 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.

The host material of the light-emitting layer includes an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compoundsPyrimidine 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) acetylacetonateiridium, bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonateiridium, bis (1-phenylquinoline) iridium), PQIr (tris (1-phenylquinoline) iridium, 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 light, Ir (ppy) can be used as the light-emitting dopant₃Examples of the fluorescent substance include phosphorescent substances such as fac tris (2-phenylpyridine) iridium and planar tris (2-phenylpyridine) iridium, and fluorescent substances such as Alq3(tris (8-hydroquinonyl) aluminum and tris (8-hydroxyquinoline) aluminum). 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.

A hole-inhibiting layer may be provided between the electron-transporting layer and the light-emitting layer, and materials known in the art may be used.

The electron transport layer can play a role in smoothing electron transport. The electron transport material is a material that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and has a high mobility to electronsThe substance (c) is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃Organic radical compounds, hydroxyl brass-metal complexes, etc., but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the electron transport property can be prevented from being lowered, and when the thickness of the electron transport layer is 50nm or less, there is an advantage that the driving voltage can be prevented from being increased in order to increase the movement of electrons when the thickness of the electron transport layer is too thick.

The electron injection layer can perform a function of smoothly injecting electrons. The electron-injecting substance is preferably a compound of: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, 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-blocking 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 in general. 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, in order to specifically explain the present specification, the details are explained by referring to examples. However, the embodiments described in the present specification may be modified into various forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present specification to those skilled in the art.

< Synthesis example >

Synthesis example 1.

Under a nitrogen atmosphere, a mixture of starting material A-1(80g) and starting material A-2(87.5g), Bis (tri-tert-butylphosphine) palladium (0) [ Bis (tri-tert-butylphosphine) -palladium (0)](0.38g)、K₂CO₃A900 mL flask of the solution (152.6g dissolved in 300mL of water (152.6g in 300mL of water)) and Tetrahydrofuran (THF) was stirred at 50 ℃ for 5 hours. After the reaction solution was cooled to room temperature, water and ethyl acetate (ethyl acetate) were added, and extraction and washing were performed. The organic layer was recovered and the extraction solvent was removed to give intermediate A-3.

Under nitrogen atmosphere, the mixture will contain A-3 and K without further purification₂CO₃(44g) And NMP (N-methyl-2-pyrrolidone) 1L flask at 150 ℃ with heating and stirring for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and 700mL of water was further added thereto, followed by stirring for further 30 minutes. Filtering the solid to obtain solid, and collecting the solid with ethyl acetate and saturated NH₄Cl solution intoAfter separating the liquid, the organic layer was recovered and MgSO₄(anhydrous) and filtering. The solvent of the filtered solution was distilled off under reduced pressure, recrystallized (hexane) and dried to obtain 58.4g of intermediate A-4.

Synthesis example 2.

After 30g of intermediate A-4 was dissolved in 300mL of acetonitrile (acetonitrile), a potassium carbonate solution (46g of potassium carbonate dissolved in 100mL of H) was further added at room temperature₂O), and then 67.5g of Nonafluorobutanesulfonyl fluoride [ Nonafluorobutanesulfonyl fluoride ] was added dropwise thereto]. After stirring for 2 hours, 200mL of water was added and the mixture was stirred for 30 minutes. Filtering the solid to obtain solid, and collecting the solid with ethyl acetate and saturated NH₄After separating the Cl solution, the organic layer was recovered and Na was added₂SO₄(anhydrous) treating and filtering. The solvent of the filtered solution was distilled off under reduced pressure, recrystallized (ethyl acetate/hexane) and dried to obtain 41g of intermediate A-5.

Synthesis example 3.

Under nitrogen, 4g of intermediate A-5, 4.8g of bis (4- (tert-butyl) phenylamine [ bis (4- (tert-butyl) phenyl) amine]7g of potassium phosphate]0.12g of bis (dibenzylideneacetone) palladium (0) [ bis (dibenzylideneacetone) palladium (0)]Pd(dba)₂0.19g of 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (Xphos) was dissolved in 100mL of bis (toluene)After the alkane, it was heated and stirred at 100 ℃ for 36 hours. After the reaction is finished, cooling the reaction liquid to room temperature, adding water and NH₄Cl solution, separating liquid, using MgSO₄(anhydrous) treating and filtering. The filtered solution was distilled off under reduced pressure and subjected to column chromatography (EA/Hx)30/1) to obtain 3.1g of compound BD-1.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -777.

Synthesis example 4.

3.0g of the compound BD-2 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

The MS measurement pattern of the above-mentioned compound BD-2 is shown in fig. 3, and a peak is observed at [ M + H + ] -897.

Synthesis example 5.

4.0g of the compound BD-3 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

The MS measurement pattern of the above-mentioned compound BD-3 is shown in fig. 4, and a peak is observed at [ M + H + ] ═ 937.

Synthesis example 6.

2.9g of the compound BD-4 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 913.

Synthesis example 7.

2.7g of the compound BD-5 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 913.

Synthesis example 8.

3.8g of the compound BD-6 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

The MS measurement pattern of the above-mentioned compound BD-6 is shown in fig. 5, and a peak was observed at [ M + H + ] -997.

Synthesis example 9.

2.9g of the compound BD-7 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] -997.

Synthesis example 10.

2.2g of the compound BD-8 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 905.

Synthesis example 11.

2.7g of the compound BD-9 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 767.

Synthesis example 12.

4.2g of the compound BD-10 was synthesized in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 1141.

Synthesis example 13.

A flask containing 28g of intermediate A-4, 5g of NaH, 400mL of Dimethylformamide (DMF) was stirred at 0 ℃ for 30 minutes under a nitrogen atmosphere. Subsequently, 21g of 4-methoxybenzyl chloride (4-methoxybenzylchloride) was further added, followed by stirring at room temperature for 8 hours. After the reaction, 400mL of water was added and the mixture was stirred for 30 minutes. Filtering the solid to obtain solid, and collecting the solid with ethyl acetate and saturated NH₄Separating with Cl solution, recovering organic layer, and adding Mg₂SO₄(anhydrous) treating and filtering. The solvent of the filtered solution was distilled off under reduced pressure, recrystallized (ethyl acetate/hexane) and then dried to obtain 31g of intermediate B-1.

31g of intermediate B-1 was dissolved in 300mL of tetrahydrofuran (anhydrous) cooled to 0 ℃ under a nitrogen atmosphere, the solution was placed in a flask, and 41.5mL of n-Butyllithium [ n-Butyllithium, 2.5M hexane solution (2.5M hexane) was slowly added dropwise]After that, the mixture was stirred for 1 hour. 13g of bromine were slowly added dropwise at 0 ℃ and then the temperature was raised to room temperature and stirred for 3 hours. After the reaction is finished, adding saturated NaS₂O₃And NaCl solution, separating, and then using MgSO₄(anhydrous) treating and filtering. The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethyl acetate/hexane), thereby obtaining 23g of intermediate B-2.

Synthesis example 14.

Intermediate B-3 was synthesized by the same method as that for synthesizing intermediate a-3 of synthesis example 1, and the next reaction was carried out without further purification.

The intermediate B-3 was charged without further purification, 9.5g of DDQ (2, 3-dichoro-5, 6-dicarbono-p-benzoquinone, 2,3-dichloro-5, 6-dicyano-p-benzoquinone), 130mL of CHCl₃A20 mL water flask was stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was filtered through celite, and a NaCl solution was added to the filtrate, followed by liquid separation with MgSO₄(anhydrous) treating and filtering. The filtered solution was distilled off under reduced pressure to give intermediate B-4 without further purification.

Intermediate B-5 was synthesized in the same manner as in the synthesis of intermediate A-5 in Synthesis example 2, and 11g of intermediate B-5 was obtained by silica gel column chromatography (eluent: ethyl acetate/hexane).

Synthesis example 15.

2.5g of the compound BD-11 was synthesized from the intermediate B-5 in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ]. 917.

Synthesis example 16.

2.2g of the compound BD-12 was synthesized from the intermediate B-5 in the same manner as in the synthesis of the compound BD-1 in Synthesis example 3.

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 865.

Synthesis example 17.

10g of intermediate B-2 were dissolved in 80mL of tetrahydro cooled to-78 ℃ under a nitrogen atmosphereFuran (anhydrous) was added to the flask, and 8.6mL of n-Butyllithium [ n-butylllithium, 2.5M in hexane (2.5M in hexane)]After that, the mixture was stirred for 30 minutes. 3.5mL of chlorotrimethylsilane (chlorotrimethylsilane) was slowly added dropwise at-78 deg.C, followed by further stirring at the same temperature for 30 minutes, then the temperature was slowly raised to room temperature, and stirring was carried out for 6 hours. After the reaction is finished, saturated NH is added₄Cl solution, after liquid separation, Na is used₂SO₄(anhydrous) treating and filtering. Intermediate C-1 was obtained without further purification and subjected to the next reaction.

Using intermediate C-1, 7.4g of intermediate C-3 was obtained in the same manner as in Synthesis example 14, except that intermediate B-5 was synthesized from intermediate B-3.

Synthesis example 18.

Compound BD-13 was synthesized from intermediate C-3 in the same manner as in the synthesis of compound BD-1 of Synthesis example 3, and 1.76g of compound BD-13 was synthesized by column chromatography (eluent: toluene/hexane).

As a result of mass spectrometry of the obtained solid, a peak was observed at [ M + H + ] ═ 837.

< example >