KR101941154B1 - Compound and organic light emitting device containing the same - Google Patents

Abstract

The present invention provides a compound and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a compound and an organic light-

The present application claims the benefit of Korean Patent Application No. 10-2016-0107188 filed on August 23, 2016 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows.

When an organic layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using this principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

BACKGROUND ART [0002] In order to improve the performance, life or efficiency of an organic light emitting device, development of an organic thin film material is continuously required.

Korean Patent Laid-Open Publication No. 2015-0135109

In this specification, compounds and organic light emitting devices containing them are described.

An embodiment of the present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

A is a substituted or unsubstituted 5-membered heterocyclic group containing O or S,

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar2 is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

p is an integer of 0 to 4, and when p is 2 or more, Ar2 are the same or different from each other,

L is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

n is an integer of 0 to 3, and when n is 2 or more, L is the same or different from each other,

R1 to R12 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

In addition, one embodiment of the present disclosure includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. Specifically, the compounds described in this specification can be used as hole injecting, hole transporting, hole injecting and hole transporting, light emitting, electron transporting, or electron injecting materials. In addition, the compounds described in this specification can preferably be used as light emitting layer materials.

A compound according to at least one embodiment of the present invention can be applied to an organic light emitting device to improve efficiency, lower driving voltage and / or lifetime characteristics.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
3 is an LC / MS spectrum of Compound 1. Fig.
4 is an LC / MS spectrum of Compound 4. Fig.
5 is an LC / MS spectrum of Compound 9;
6 is an LC / MS spectrum of Compound 14. Fig.
Fig. 7 is an LC / MS spectrum of Compound 16; Fig.
8 is an LC / MS spectrum of Compound 17;
Figure 9 is an LC / MS spectrum of compound 20;
10 is an LC / MS spectrum of Compound 26. Fig.
11 is a diagram showing an LC / MS spectrum of Compound 30. Fig.

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

An embodiment of the present invention provides a compound represented by the above formula (1).

In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

In this specification, when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.

Examples of substituents in the present specification are described below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amine group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; A substituted or unsubstituted silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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

In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiRR'R ", wherein R, R 'and R" are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl groups. Do not.

In the present specification, the boron group may be represented by the formula of -BRR ', wherein R and R' are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically 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, examples of the halogen group include fluorine, chlorine, bromine or iodine.

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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 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 cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkoxy group is not particularly limited, but preferably has 1 to 40 carbon atoms. According to one embodiment, the number of carbon atoms in the alkoxy group is from 1 to 10. According to another embodiment, the number of carbon atoms of the alkoxy group is from 1 to 6. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an isoamyloxy group and a hexyloxy group.

In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , A diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, and the like, but are not limited thereto.

In the present specification, examples of the arylamine group include 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 two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group containing at least two heterocyclic groups may contain a monocyclic heterocyclic group, a polycyclic heterocyclic group, or a monocyclic heterocyclic group and a polycyclic heterocyclic group at the same time.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group, a fluorenyl group and a triphenylene group.

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

,

,

,

,

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

,

And

And the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, A benzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenoxazinyl group , A phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto. The heterocyclic group includes an aliphatic heterocyclic group and an aromatic heterocyclic group.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the arylphosphine group, the aralkyl group, the aralkylamine group, the aralkenyl group, the alkylaryl group, the arylamine group and the arylheteroarylamine group, The description of one aryl group may be applied.

In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group can be applied to the alkyl group described above.

In the present specification, the heteroaryl group, the heteroarylamine group, and the heteroaryl group in the arylheteroarylamine group may be aromatic, but the description of the above-mentioned heterocyclic group may be applied.

In the present specification, the alkenyl group in the aralkenyl group can be applied to the description of the alkenyl group described above.

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, the description of the aforementioned heterocyclic group can be applied, except that the divalent heterocyclic group is divalent.

In the present specification, in the substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

The hydrocarbon ring may be selected from the examples of the cycloalkyl group or the aryl group.

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (2) or (3).

(2)

(3)

In the general formula (2) or (3)

Ar1, Ar2, L, p, n and R1 to R12 are as defined in formula (1)

X is O or S;

According to one embodiment of the present invention, R1 to R12 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, R1 to R12 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; An ester group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, R1 to R12 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.

According to one embodiment of the present invention, R1 to R12 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R1 to R12 are hydrogen.

According to one embodiment of the present disclosure, Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, Ar2 is hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted phenyl group.

According to one embodiment of the present invention, Ar1 is a phenyl group substituted with a nitrile group.

According to one embodiment of the present invention, Ar1 is a phenyl group substituted with deuterium.

According to one embodiment of the present invention, Ar1 is a phenyl group substituted with a phenyl group substituted with deuterium.

According to one embodiment of the present invention, Ar1 is a phenyl group substituted by a heterocyclic group.

According to one embodiment of the present invention, Ar1 is a phenyl group substituted with a pyridine group.

According to one embodiment of the present invention, Ar1 is a phenyl group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted biphenyl group.

According to one embodiment of the present invention, Ar1 is a biphenyl group substituted with deuterium.

According to one embodiment of the present invention, Ar1 is a biphenyl group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted phenanthryl group.

According to one embodiment of the present invention, Ar1 is a phenanthryl group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar1 is a fluorenyl group substituted with a methyl group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted triphenylene group.

According to one embodiment of the present invention, Ar1 is a triphenylene group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted naphthyl group.

According to one embodiment of the present invention, Ar1 is a naphthyl group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted fluoranthene group.

According to one embodiment of the present invention, Ar1 is a fluoranthene group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted carbazole group.

According to one embodiment of the present invention, Ar1 is a carbazole group substituted with a phenyl group.

According to one embodiment of the present invention, Ar1 is a carbazole group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted dibenzofurane group.

According to one embodiment of the present invention, Ar1 is a dibenzofurane group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted dibenzothiophene group.

According to one embodiment of the present invention, Ar1 is a dibenzothiophene group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted benzocarbazole group.

According to one embodiment of the present invention, Ar1 is a benzocarbazole group substituted with a phenyl group.

According to one embodiment of the present invention, Ar1 is a benzocarbazole group.

According to one embodiment of the present invention, Ar1 is a substituted or unsubstituted pyridine group.

According to one embodiment of the present invention, Ar1 is a pyridine group.

According to one embodiment of the present disclosure, Ar2 is hydrogen.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted phenyl group.

According to one embodiment of the present disclosure, Ar2 is a phenyl group substituted with deuterium.

According to one embodiment of the present invention, Ar2 is a phenyl group substituted with a nitrile group.

According to one embodiment of the present invention, Ar2 is a phenyl group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted naphthyl group.

According to one embodiment of the present invention, Ar2 is a naphthyl group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted biphenyl group.

According to one embodiment of the present invention, Ar2 is a biphenyl group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted dibenzofurane group.

According to one embodiment of the present invention, Ar2 is a dibenzofurane group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted dibenzothiophene group.

According to one embodiment of the present invention, Ar2 is a dibenzothiophene group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted carbazole group.

According to one embodiment of the present invention, Ar2 is a carbazole group substituted with a phenyl group.

According to one embodiment of the present invention, Ar2 is a carbazole group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar2 is a fluorenyl group substituted with a methyl group.

According to one embodiment of the present invention, Ar2 is a substituted or unsubstituted pyridine group.

According to one embodiment of the present invention, Ar2 is a pyridine group.

In one embodiment of the present specification, p is an integer of 0 to 4.

In one embodiment of the present specification, p is an integer of 0 to 2.

In one embodiment of the present disclosure, p is zero.

In one embodiment of the present disclosure, p is one.

In one embodiment of the present disclosure, p is two.

According to one embodiment of the present disclosure, L is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group.

According to one embodiment of the present invention, L is a substituted or unsubstituted arylene group.

According to one embodiment of the present disclosure, L is a phenylene group.

According to one embodiment of the present disclosure, L is a naphthylene group.

According to one embodiment of the present specification, L is a substituted or unsubstituted divalent heterocyclic group.

According to one embodiment of the present invention, L is a divalent pyridine group.

According to one embodiment of the present invention, L is a divalent pyrimidine group.

According to one embodiment of the present disclosure, L is a divalent pyrazine group.

According to one embodiment of the present disclosure, n is an integer from 0 to 3.

According to one embodiment of the present disclosure, n is 0 or 1.

According to one embodiment of the present invention, the compound of Formula 1 may be selected from the following structural formulas.

According to one embodiment of the present invention, the compound of Formula 1 described above is prepared by using Buchwald-Hartwig coupling reaction, Suzuki coupling reaction, or the like as a typical reaction.

Concretely, various Ar1 and Ar2 were bound to a five-ring pyrimidine derivative containing oxygen or sulfur using a Suzuki coupling reaction or a Buchwald-Hartwig coupling reaction. Then, 7H-dibenzo [c, g] carbazole to synthesize the compound of the present invention.

The reaction formula is as shown in Reaction Scheme 1 or Reaction Scheme 2 below.

[Reaction Scheme 1]

[Reaction Scheme 2]

Ar 1, Ar 2, X, L, p, and n are the same as defined in Formula (1)

X < _{1 >} is bromine or chlorine.

Also, the present invention provides an organic light emitting device comprising the compound represented by Formula 1.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.

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

In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting holes and transporting holes, and the hole injecting layer, the hole transporting layer, Includes the compound of the above formula (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound of the general formula (1).

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a host material, and further includes another host material.

In one embodiment of the present invention, the organic layer includes a light emitting layer, the light emitting layer includes the compound of Formula 1, and further includes a dopant compound.

In one embodiment of the present disclosure, the dopant compound is a phosphorescent dopant.

In one embodiment of the present disclosure, the dopant compound is an iodide based complex.

In one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include the compound and the dopant compound in a ratio of 100: 1 to 5: 5.

In the present specification, the following compounds Dp-1 to Dp-27 may be used as the dopant material, but the present invention is not limited thereto.

In one embodiment of the present invention, the organic material layer includes an electron transport layer, an electron injection layer, or a layer which simultaneously transports electrons and electrons, and the electron transport layer, the electron injection layer, The compound of formula (1).

In one embodiment of the present invention, the organic layer includes an electron inhibiting layer, and the electron inhibiting layer includes the compound of the above formula (1).

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; Wherein at least one of the two or more organic layers includes the compound of Formula 1, wherein the organic layer comprises at least two organic layers including at least two organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode . In one embodiment, the two or more organic layers may be selected from the group consisting of an electron transporting layer, an electron injecting layer, a layer that simultaneously transports electrons and an electron injecting layer, and a hole blocking layer.

In one embodiment of the present invention, the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the compound of the above formula (1). Specifically, in one embodiment of the present invention, the compound of Formula 1 may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.

In one embodiment of the present invention, when the compound of Formula 1 is contained in each of the two or more electron transporting layers, the materials other than the compound of Formula 1 may be the same or different from each other.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

 In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.

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

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound of the above formula (1).

When the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

 The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of Formula 1, that is, the compound represented by Formula 1.

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. However, the manufacturing method is not limited thereto.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In one embodiment of the present invention, 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 a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode 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 oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may further include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound in addition to the compound represented by the above formula (1). Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and ferriflantene having an arylamine group. Examples of the styrylamine compound include substituted or unsubstituted Substituted arylamine in which at least one aryl vinyl group is substituted, wherein at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamine group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

In one embodiment of the present invention, the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

Synthesis Example 1. Synthesis of Intermediate 1

20.0 g (1.0 eq) of Compound A-1 (2,4-dichlorobenzo [4,5] thieno [3,2-d] pyrimidine), 9,9- for yl) boronic acid), 16.66g (1.0eq) and tetrakis (triphenylphosphine) palladium _{(0) (Pd (PPh 3} ) 4) 0.45g (0.005eq) in water is dissolved in tetrahydrofuran (THF), 200ml 11.37 g (1.05 eq) of potassium carbonate (K ₂ CO ₃ ) dissolved therein was added and the mixture was refluxed and stirred. After 3 hours, when the reaction was completed, the reaction solution was cooled and the aqueous solution layer was removed, and the organic solvent was removed by decompression. Then, it was completely dissolved in chloroform (CHCl ₃ ), washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in a refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 23.95 g (yield: 74%) of intermediate 1. [M + H] < + > = 413

Synthesis Example 2. Synthesis of Intermediate 2

Intermediate 2 was synthesized in the same manner as in Synthesis Example 1, except that Compound B-2 was used instead of Compound B-1 in Synthesis Example 1. [M + H] < + > = 421

Synthesis Example 3. Synthesis of Intermediate 3

(1) Synthesis of intermediate 3-1

30.0 g (1.0 eq) of Compound A-2 (8-bromo-2,4-dichlorobenzo [4,5] thieno [3,2-d] pyrimidine) g (1.0eq), [1,1'- bis (diphenylphosphino) ferrocene] dichloropalladium (II) (Pd (dppf) Cl _2), dissolved 0.32g (0.005eq) in 300ml THF was dissolved in water, K ₂ 13.03 g (1.05 eq) of CO ₃ was added, and the mixture was refluxed and stirred. After 3 hours, when the reaction was completed, the reaction solution was cooled and the aqueous solution layer was removed, and the organic solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 21.14 g (yield: 70%) of Intermediate 3-1. [M + H] < + > = 337

(2) Synthesis of intermediate 3

Dissolve the intermediate 3-1 21.14g (1.0eq), compound C-1 (naphthalen-2- ylboronic acid) 10.81g (1.0eq), Pd (PPh 3) 4 0.36g (0.005eq) in 200ml THF was dissolved in water 9.12 g (1.05 eq) of K ₂ CO ₃ was added and the mixture was refluxed and stirred. After 3 hours, when the reaction was completed, the reaction solution was cooled and the aqueous solution layer was removed, and the organic solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 20.71 g (yield: 77%) of Intermediate 3. [M + H] < + > = 644

Synthesis Example 4. Synthesis of Intermediate 4

Intermediate 4 was synthesized in the same manner as in Synthesis Example 1 except that Compound B-4 was used instead of Compound B-1 in Synthesis Example 1. [M + H] < + > = 387

Synthesis Example 5. Synthesis of Intermediate 5

(1) Synthesis of intermediate 5-2

30.0 g (1.0 eq) of Compound A-2 (8-bromo-2,4-dichlorobenzo [4,5] thieno [3,2-d] pyrimidine), 10.95 g (1.0 eq) of Compound B- And 0.32 g (0.005 eq) of Pd (dppf) Cl ₂ were dissolved in 300 ml of THF, 13.03 g (1.05 eq) of K ₂ CO ₃ dissolved in water was added, and the mixture was refluxed and stirred. After 3 hours, when the reaction was completed, the reaction solution was cooled and the aqueous solution layer was removed, and the organic solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 20.82 g (yield: 70%) of Intermediate 5-2. [M + H] < + > = 332

(2) Synthesis of Intermediate 5-1

Dissolve the intermediate 5-2 20.82g (1.0eq), compound C-1 (naphthalen-2- ylboronic acid) 10.81g (PPh 3) (1.0eq) and Pd ₄ 0.36g (0.005eq) in 200ml THF was dissolved in water 9.12 g (1.05 eq) of K ₂ CO ₃ was added and the mixture was refluxed and stirred. After 3 hours, when the reaction was completed, the reaction solution was cooled and the aqueous solution layer was removed, and the organic solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 19.93 g (yield: 75%) of Intermediate 5-1. [M + H] < + > = 423

(3) Synthesis of intermediate 5

Intermediate 5-1 19.93g (1.0eq), the compound C-2 ((4-chloronaphthalen -1-yl) boronic acid) 9.72g (1.0eq) and _{Pd (PPh 3) 4 0.27g (} 0.005eq) THF 200ml And 6.83 g (1.05 eq) of K ₂ CO ₃ dissolved in water were added, and the mixture was refluxed and stirred. After 5 hours, the reaction was completed. After cooling, the aqueous layer was removed and the organic solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.37 g (yield: 71%) of intermediate 5. [M + H] = 550

Synthesis Example 6. Synthesis of Intermediate 6

(1) Synthesis of intermediate 6-1

Intermediate 6-1 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Compound A-1 and Compound B-6 were used instead of Intermediate 5-2 and Compound C-1 in Synthesis Example 5 (2) Respectively.

(2) Synthesis of intermediate 6

Intermediate 6 was synthesized in the same manner as in (3) of Synthesis Example 5 except that Intermediate 6-1 and Compound C-3 were used instead of Intermediate 5-1 and Compound C-2 in Synthesis Example 5 (3). [M + H] < + > = 480

Synthesis Example 7. Synthesis of Intermediate 7

30.0 g (1.0 eq) of Compound A-3 (7-bromo-2,4-dichlorobenzo [4,5] thieno [3,2-d] pyrimidine), 21.90 0.32 g (0.005 eq) of Pd (dppf) Cl ₂ was dissolved in 300 ml of THF and 23.37 g (2.05 eq) of K ₂ CO ₃ dissolved in water was added thereto, followed by refluxing and stirring. After 5 hours, the reaction was completed. After cooling, the aqueous layer was removed and the organic solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in a refluxing state, and the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 25.10 g (yield: 73%) of intermediate 7. [M + H] = 383

Synthesis 8. Synthesis of Intermediate 8

(1) Synthesis of Intermediate 8-1

Intermediate 8-1 was synthesized in the same manner as in (1) of Synthesis Example 5 except that Compound B-4 was used instead of Compound B-5 in Synthesis Example 5 (1).

(2) Synthesis of intermediate 8

Intermediate 8 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Intermediate 8-1 and Compound C-3 were used instead of Intermediate 5-1 and Compound C-1 in Synthesis Example 5 (2). [M + H] < + > = 463

Synthesis Example 9. Synthesis of Intermediate 9

Intermediate 9 was synthesized in the same manner as in Synthesis Example 1 except that the compounds A-4 and B-7 were used instead of the compounds A-1 and B-1 in Synthesis Example 1. [M + H] < + > = 462

Synthesis Example 10. Synthesis of Intermediate 10

Intermediate 10 was synthesized in the same manner as in Synthesis Example 1, except that the compounds A-4 and B-8 were used instead of the compounds A-1 and B-1 in Synthesis Example 1. [M + H] < + > = 397

Synthesis Example 11. Synthesis of Intermediate 11

(1) Synthesis of Intermediate 11-1

Intermediate 11-1 was synthesized in the same manner as in (1) of Synthesis Example 3 except that Compound A-5 and Compound B-9 were used instead of Compound A-2 and Compound B-3 in Synthesis Example 3 (1) Respectively.

(2) Synthesis of intermediate 11

Intermediate 11 was synthesized in the same manner as in (2) of Synthesis Example 3, except that Intermediate 11-1 was used instead of Intermediate 3-1 in Synthesis Example 3 (2). [M + H] < + > = 448

Synthesis Example 12. Synthesis of Intermediate 12

(1) Synthesis of intermediate 12-1

Intermediate 12-1 was synthesized in the same manner as in (1) of Synthesis Example 5 except that Compound A-5 was used instead of Compound A-2 in Synthesis Example 5 (1).

(2) Synthesis of intermediate 12-2

Intermediate 12-2 was synthesized in the same manner as in (2) of Synthesis Example 5, except that Intermediate 12-1 was used instead of Intermediate 5-2 in Synthesis Example 5 (2).

(3) Synthesis of Intermediate 12

Intermediate 12 was synthesized in the same manner as in (3) of Synthesis Example 5 except that Intermediate 12-2 and Compound C-4 were used instead of Intermediate 5-1 and Compound C-2 in Synthesis Example 5 (3). [M + H] < + > = 578

Synthesis Example 13. Synthesis of Intermediate 13

(1) Synthesis of Intermediate 13-1

Intermediate 13-1 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Compound A-4 was used instead of Intermediate 5-2 in Synthesis Example 5 (2).

(2) Synthesis of Intermediate 13

Intermediate 13 was synthesized in the same manner as in (3) of Synthesis Example 5 except that Intermediate 13-1 and Compound C-5 were used instead of Intermediate 5-1 and Compound C-2 in Synthesis Example 5 (3). [M + H] < + > = 473

Synthesis Example 14. Synthesis of Intermediate 14

(1) Synthesis of Intermediate 14-1

Intermediate 14-1 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Compound A-4 and Compound B-10 were used instead of Intermediate 5-2 and Compound C-1 in Synthesis Example 5 (2) Respectively.

(2) Synthesis of Intermediate 14

Intermediate 14 was synthesized in the same manner as in (3) of Synthesis Example 5 except that Intermediate 14-1 and Compound C-3 were used instead of Intermediate 5-1 and Compound C-2 in Synthesis Example 5 (3). [M + H] < + > = 539

Synthesis Example 15. Synthesis of Intermediate 15

(1) Synthesis of intermediate 15-1

Intermediate 15-1 was synthesized in the same manner as in (1) of Synthesis Example 3 except that Compound A-6 and Compound B-5 were used instead of Compound A-2 and Compound B-3 in Synthesis Example 3 (1) Respectively.

(2) Synthesis of intermediate 15

Intermediate 15 was synthesized in the same manner as in (2) of Synthesis Example 3 except that Intermediate 15-1 and Compound B-3 were used instead of Intermediate 3-1 and Compound C-1 in Synthesis Example 3 (2). [M + H] = 378

Synthesis Example 16. Synthesis of Intermediate 16

Intermediate 16 was synthesized in the same manner as in Synthesis Example 1, except that Compound A-7 and Compound B-9 were used instead of Compound A-1 and Compound B-1 in Synthesis Example 1. [M + H] < + > = 306

Synthesis Example 17. Synthesis of Intermediate 17

Intermediate 17 was synthesized in the same manner as in Synthesis Example 1, except that Compound A-7 and Compound B-11 were used instead of Compound A-1 and Compound B-1 in Synthesis Example 1. [M + H] = 496

Synthesis Example 18. Synthesis of Intermediate 18

(1) Synthesis of intermediate 18-1

Intermediate 18-1 was synthesized in the same manner as in (1) of Synthesis Example 3 except that Compound A-8 and Compound C-1 were used instead of Compound A-2 and Compound B-3 in Synthesis Example 3 (1) Respectively.

(2) Synthesis of Intermediate 18

Intermediate 18 was synthesized in the same manner as in (2) of Synthesis Example 3 except that Intermediate 18-1 and Compound C-6 were used instead of Intermediate 3-1 and Compound C-1 in Synthesis Example 3 (2). [M + H] < + > = 408

Synthesis Example 19. Synthesis of Intermediate 19

Intermediate 19 was synthesized in the same manner as in Synthesis Example 1, except that Compound A-7 and Compound B-12 were used instead of Compound A-1 and Compound B-1 in Synthesis Example 1. [M + H] < + > = 387

Synthesis Example 20. Synthesis of Intermediate 20

(1) Synthesis of intermediate 20-1

Intermediate 20-1 was synthesized by the same method as in (1) of Synthesis Example 5 except that Compound A-8 and Compound B-9 were used instead of Compound A-2 and Compound B-5 in Synthesis Example 5 (1) Respectively.

(2) Synthesis of intermediate 20-2

Intermediate 20-2 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Intermediate 20-1 was used instead of Intermediate 5-2 in Synthesis Example 5 (2).

(3) Synthesis of intermediate 20

Intermediate 20 was synthesized in the same manner as in (3) of Synthesis Example 5 except that Intermediate 20-2 and Compound C-7 were used instead of Intermediate 5-1 and Compound C-2 in Synthesis Example 5 (3). [M + H] = 484

Synthesis Example 21. Synthesis of Intermediate 21

(1) Synthesis of intermediate 21-1

Intermediate 21-1 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Compound A-7 and Compound B-13 were used instead of Intermediate 5-2 and Compound C-1 in Synthesis Example 5 (2) Respectively.

(2) Synthesis of intermediate 21

Intermediate 21 was synthesized in the same manner as in (3) of Synthesis Example 5 except that Intermediate 21-1 and Compound C-2 were used instead of Intermediate 5-1 and Compound C-2 in Synthesis Example 5 (3). [M + H] < + > = 497

Synthesis 22. Synthesis of Intermediate 22

(1) Synthesis of Intermediate 22-1

Intermediate 22-1 was synthesized in the same manner as in (1) of Synthesis Example 3 except that Compound A-9 and Compound B-5 were used instead of Compound A-2 and Compound B-3 in Synthesis Example 3 (1) Respectively.

(2) Synthesis of intermediate 22

Intermediate 22 was synthesized in the same manner as in (2) of Synthesis Example 3 except that Intermediate 22-1 and Compound C-6 were used instead of Intermediate 3-1 and Compound C-1 in Synthesis Example 3 (2). [M + H] < + > = 434

Synthesis Example 23. Synthesis of Intermediate 23

(1) Synthesis of intermediate 23-1

Intermediate 23-1 was synthesized in the same manner as in (1) of Synthesis Example 3 except that Compound A-10 and Compound B-14 were used instead of Compound A-2 and Compound B-3 in Synthesis Example 3 (1) Respectively.

(2) Synthesis of intermediate 23

Intermediate 23 was synthesized in the same manner as in (2) of Synthesis Example 3 except that Intermediate 23-1 and Compound B-9 were used instead of Intermediate 3-1 and Compound C-1 in Synthesis Example 3 (2). [M + H] < + > = 463

Synthesis 24. Synthesis of intermediate 24

Intermediate 24 was synthesized in the same manner as in Synthesis Example 1 except that Compound A-11 and Compound B-15 were used instead of Compound A-1 and Compound B-1 in Synthesis Example 1. [M + H] < + > = 362

Synthesis 25. Synthesis of Intermediate 25

Intermediate 25 was synthesized in the same manner as in Synthesis Example 1, except that Compound A-11 and Compound B-16 were used instead of Compound A-1 and Compound B-1 in Synthesis Example 1. [M + H] < / RTI > = 282

Synthesis Example 26 Synthesis of Intermediate 26

Intermediate 26 was synthesized in the same manner as in Synthesis Example 1 except that Compound A-12 and Compound B-5 were used instead of Compound A-1 and Compound B-1 in Synthesis Example 1. [M + H] < + > = 433

Synthesis Example 27. Synthesis of Intermediate 27

(1) Synthesis of intermediate 27-1

Intermediate 27-1 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Compound A-11 and Compound B-2 were used instead of Intermediate 5-2 and Compound C-1 in Synthesis Example 5 (2) Respectively.

(2) Synthesis of intermediate 27

Intermediate 27 was synthesized in the same manner as in (3) of Synthesis Example 5 except that Intermediate 27-1 and Compound C-3 were used instead of Intermediate 5-1 and Compound C-2 in Synthesis Example 5 (3). [M + H] = 481

Synthesis Example 28 Synthesis of Intermediate 28

(1) Synthesis of intermediate 28-1

Intermediate 28-1 was synthesized in the same manner as in (1) of Synthesis Example 5 except that Compound A-13 was used instead of Compound A-2 in Synthesis Example 5 (1).

(2) Synthesis of intermediate 28-2

Intermediate 28-2 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Compound Intermediate 28-1 was used instead of Intermediate 5-2 in Synthesis Example 5 (2).

(2) Synthesis of intermediate 28

Intermediate 28 was synthesized in the same manner as in (3) of Synthesis Example 5 except that Intermediate 28-2 and Compound C-8 were used instead of Intermediate 5-1 and Compound C-2 in Synthesis Example 5 (3). [M + H] = 485

Synthesis Example 29. Synthesis of Intermediate 29

(1) Synthesis of intermediate 29-1

Intermediate 29-1 was synthesized in the same manner as in (2) of Synthesis Example 5 except that Compound A-11 and Compound B-1 were used instead of Intermediate 5-2 and Compound C-1 in Synthesis Example 5 (2) Respectively.

(2) Synthesis of intermediate 29

Intermediate 29 was synthesized in the same manner as in (3) of Synthesis Example 5, except that Intermediate 29-1 was used instead of Intermediate 5-1 in Synthesis Example 5 (3). [M + H] < + > = 524

Synthesis Example 30. Synthesis of Intermediate 30

(1) Synthesis of intermediate 30-1

Intermediate 30-1 was synthesized in the same manner as in (1) of Synthesis Example 3 except that Compound A-14 and Compound B-5 were used instead of Compound A-2 and Compound B-3 in Synthesis Example 3 (1) Respectively.

(2) Synthesis of intermediate 30

Intermediate 30 was synthesized in the same manner as in (2) of Synthesis Example 3 except that Intermediate 30-1 and Compound B-4 were used instead of Intermediate 3-1 and Compound C-1 in Synthesis Example 3 (2). [M + H] < + > = 447

Synthesis Example 31. Synthesis of Compound 1

Compound D (7H-dibenzo [c, g] carbazole) 10.0g (1.0eq), intermediate 1 16.99g (1.1eq) and K ₃ PO ₄ 15.88g reflux dissolved in dimethyl acetamide (DMAC) to 200ml (2.0eq) And stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.61 g (yield: 69%) of Compound 1. [M + H] < + > = 644

3 is an LC / MS spectrum of Compound 1. Fig.

Synthesis Example 32. Synthesis of Compound 2

10.0 g (1.0 eq) of compound D (7H-dibenzo [c, g] carbazole), 17.15 g (1.1 eq) of intermediate 2 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.55 g (Yield: 72%) of Compound 2. [M + H] = 652

Synthesis Example 33. Synthesis of Compound 3

10.0 g (1.0 eq) of compound D (7H-dibenzo [c, g] carbazole), 17.60 g (1.1 eq) of intermediate 3 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.48 g (yield: 75%) of Compound 3. [M + H] = 659

Synthesis Example 34. Synthesis of Compound 4

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 15.91 g (1.1 eq) of the intermediate 4 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.40 g (Yield: 71%) of Compound 4. [M + H] = 618

4 is an LC / MS spectrum of Compound 4. Fig.

Synthesis Example 35. Synthesis of Compound 5

18.27 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 22.59 g (1.1 eq) of Intermediate 5, 7.18 g (2.0 eq) of sodium t-butoxide (NaOtBu) 0.10 g (0.005 eq) of bis (tri- tert-butylphosphine) palladium (0) and Pd (t-Bu ₃ P) ₂ were dissolved in 200 ml of xylene, did. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 21.29 g (yield: 73%) of Compound 5. [M + H] < + > = 780

Synthesis Example 36. Synthesis of Compound 6

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 6 19.71g (1.1eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.79 g (yield: 67%) of Compound 6. [M + H] < + > = 710

Synthesis Example 37. Synthesis of Compound 7

10.0 g (1.0 eq) of compound D (7H-dibenzo [c, g] carbazole), 15.75 g (1.1 eq) of intermediate 7 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.30 g (yield: 74%) of Compound 7. [M + H] < + > = 614

Synthesis Example 38. Synthesis of Compound 8

10.0 g (1.0 eq) of Compound D (7 eq.), 19.04 g (1.1 eq) of Intermediate 8 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.94 g (yield: 73%) of Compound 8. [M + H] = 694

Synthesis Example 39. Synthesis of Compound 9

10.0 g (1.0 eq) of Compound D (7 eq.), 19.00 g (1.1 eq) of Intermediate 9 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.14 g (yield: 70%) of Compound 9. [M + H] < / RTI > = 693

5 is an LC / MS spectrum of Compound 9;

Synthesis Example 40. Synthesis of Compound 10

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 16.33 g (1.1 eq) of the intermediate 10 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.20 g (yield: 69%) of Compound 10. [M + H] < / RTI > = 628

Synthesis Example 41. Synthesis of Compound 11

10.0 g (1.0 eq) of compound D (7 eq.), 18.43 g (1.1 eq) of intermediate 11 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.50 g (yield: 65%) of Compound 11. [M + H] = 679

Synthesis Example 42 Synthesis of Compound 12

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 12 23.74g (1.1 eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 20.85 g (yield: 69%) of Compound 12. [M + H] < + > = 808

Synthesis Example 43. Synthesis of Compound 13

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 13 19.46g (1.1eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.64 g (yield: 67%) of Compound 13. [M + H] < + > = 704

Synthesis Example 44. Synthesis of Compound 14

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 14 22.14g (1.1eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 20.42 g (yield: 71%) of Compound 14. [M + H] < / RTI > = 769

6 is an LC / MS spectrum of Compound 14. Fig.

Synthesis Example 45. Synthesis of Compound 15

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 15.54 g (1.1 eq) of the intermediate 15 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 15.94 g (yield: 70%) of Compound 15. [M + H] = 609

Synthesis Example 46. Synthesis of Compound 16

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 12.57 g (1.1 eq) of the intermediate 16 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 14.25 g (yield: 71%) of Compound 16. [M + H] < + > = 537

Fig. 7 is an LC / MS spectrum of Compound 16; Fig.

Synthesis Example 47. Synthesis of Compound 17

10.0 g (1.0 eq) of compound D (7 eq.), 20.36 g (1.1 eq) of intermediate 17 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.76 g (yield: 69%) of Compound 17. [M + H] < + > = 727

8 is an LC / MS spectrum of Compound 17;

Synthesis Example 48. Synthesis of Compound 18

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 16.78 g (1.1 eq) of the intermediate 18 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.44 g (yield: 73%) of Compound 18. [M + H] = 639

Synthesis Example 49. Synthesis of Compound 19

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 15.91 g (1.1 eq) of the intermediate 19 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.17 g (yield: 70%) of Compound 19. [M + H] = 618

Synthesis Example 50. Synthesis of Compound 20

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 20 19.91g (1.1eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.98 g (yield: 71%) of Compound 20. [M + H] = 715

Figure 9 is an LC / MS spectrum of compound 20;

Synthesis Example 51. Synthesis of Compound 21

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 21 20.44g (1.1eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.24 g (yield: 67%) of Compound 21. [M + H] < + > = 728

Synthesis Example 52. Synthesis of Compound 22

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 17.85 g (1.1 eq) of the intermediate 22 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.90 g (yield: 72%) of Compound 22. [M + H] < + > = 665

Synthesis Example 53. Synthesis of Compound 23

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 19.04 g (1.1 eq) of the intermediate 23 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 mL of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 18.16 g (yield: 70%) of Compound 23. [M + H] = 694

Synthesis Example 54. Synthesis of Compound 24

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 14.88 g (1.1 eq) of the intermediate 24 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.85 g (yield: 76%) of Compound 24. [M + H] < + > = 593

Synthesis Example 55. Synthesis of Compound 25

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 11.59 g (1.1 eq) of the intermediate 25 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 13.80 g (yield: 72%) of Compound 25. [M + H] < + > = 513

Synthesis Example 56 Synthesis of Compound 26

10.0 g (1.0 eq) of the compound D (7H-dibenzo [c, g] carbazole), 17.81 g (1.1 eq) of the intermediate 26 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Again, ethyl acetate was added in a refluxing state, the crystals were dropped, cooled and filtered. This was subjected to column chromatography to obtain 17.38 g (yield: 70%) of Compound 26. [M + H] = 664

10 is an LC / MS spectrum of Compound 26. Fig.

Synthesis Example 57. Synthesis of Compound 27

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 27 19.78g (1.1eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 19.70 g (yield: 74%) of Compound 27. [M + H] = 712

Synthesis Example 58. Synthesis of Compound 28

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 28 19.95g (1.1eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 16.86 g (yield: 63%) of Compound 28. [M + H] < + > = 716

Synthesis Example 59. Synthesis of Compound 29

Compound D (7H-dibenzo [c, g] carbazole) 18.27g (1.0eq), intermediate 29 21.52g (1.1eq), NaOtBu 7.18g (2.0eq) and _{Pd (t-Bu 3 P)} 2 0.10g (0.005 eq) was dissolved in 200 ml of xylene and refluxed and stirred. After the reaction was completed after 5 hours, the solvent was removed by decompression. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 19.17 g (yield: 68%) of Compound 29. [M + H] < + > = 754

Synthesis Example 60. Synthesis of Compound 30

10.0 g (1.0 eq) of Compound D (7 eq.), 18.38 g (1.1 eq) of Intermediate 30 and 15.88 g (2.0 eq) of K ₃ PO ₄ were dissolved in 200 ml of DMAC and refluxed and stirred. After 3 hours, when the reaction was completed, the crystals were cooled down and filtered. Then, it was completely dissolved in CHCl ₃ , washed with water, and further decompressed to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 17.74 g (yield: 70%) of Compound 30. [M + H] = 678

11 is a diagram showing an LC / MS spectrum of Compound 30. Fig.

Example 1

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. The following HAT-CN compound was thermally vacuum-deposited on the ITO transparent electrode prepared above to a thickness of 500 Å to form a hole injection layer. The HT1 compound was thermally vacuum deposited on the hole injection layer to a thickness of 800 Å, and HT2 compound was vacuum deposited thereon to a thickness of 500 Å to form a hole transport layer. Compound 1 and dopant Dp-7 compound were vacuum-deposited as a host to a thickness of 300 Å in the light emitting layer. The amount of the dopant was 3 wt% based on the total amount of the host and the dopant. An ET1 material was vacuum deposited on the light emitting layer to form a hole blocking layer, and an ET2 material and LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron transport layer of 250 ANGSTROM. Lithium fulleride (LiF) was sequentially deposited on the electron transporting layer to a thickness of 10 Å, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode. In the above process, the deposition rate of the organic material was maintained at 0.4 A / sec to 0.7 A / sec, the deposition rate of lithium fluoride at the cathode was 0.3 A / sec and the deposition rate of aluminum was maintained at 2 A / sec. × 10 ^{- 7} torr To 5 × 10 ^- to ⁸ torr was maintained.

HAT-CN, HT1, HT2, ET1 and ET2 are as follows.

Example 2

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in Example 1.

Example 3

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 3 was used instead of Compound 1 in Example 1,

Example 4

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in Example 1.

Example 5

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 5 was used instead of Compound 1 in Example 1.

Example 6

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 6 was used instead of Compound 1 in Example 1.

Example 7

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 7 was used instead of Compound 1 in Example 1.

Example 8

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 8 was used instead of Compound 1 in Example 1.

Example 9

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 in Example 1.

Example 10

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 10 was used instead of Compound 1 in Example 1.

Example 11

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 11 was used instead of Compound 1 in Example 1.

Example 12

An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 12 was used instead of Compound 1 in Example 1.

Example 13

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 13 was used instead of Compound 1 in Example 1.

Example 14

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 14 was used instead of Compound 1 in Example 1.

Example 15

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 in Example 1.

Example 16

An organic luminescent device was fabricated in the same manner as in Example 1, except that Compound 16 was used instead of Compound 1 in Example 1.

Example 17

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 17 was used instead of Compound 1 in Example 1.

Example 18

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 18 was used instead of Compound 1 in Example 1.

Example 19

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 19 was used instead of Compound 1 in Example 1.

Example 20

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 20 was used instead of Compound 1 in Example 1.

Example 21

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 21 was used instead of Compound 1 in Example 1.

Example 22

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 22 was used instead of Compound 1 in Example 1.

Example 23

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 23 was used instead of Compound 1 in Example 1.

Example 24

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 24 was used instead of Compound 1 in Example 1.

Example 25

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 25 was used instead of Compound 1 in Example 1.

Example 26

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 26 was used instead of Compound 1 in Example 1.

Example 27

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 27 was used instead of Compound 1 in Example 1.

Example 28

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 28 was used instead of Compound 1 in Example 1.

Example 29

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 29 was used instead of Compound 1 in Example 1.

Example 30

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 30 was used instead of Compound 1 in Example 1.

Comparative Example 1

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C1 was used instead of the compound 1 in Example 1.

Comparative Example 2

An organic luminescent device was fabricated in the same manner as in Example 1, except that the compound C2 was used instead of the compound 1 in Example 1.

Comparative Example 3

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C3 was used instead of the compound 1 in Example 1.

Comparative Example 4

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C4 was used instead of the compound 1 in Example 1.

Comparative Example 5

An organic luminescent device was fabricated in the same manner as in Example 1, except that the compound C5 was used instead of the compound 1 in Example 1.

Comparative Example 6

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound C6 was used instead of Compound 1 in Example 1.

Comparative Example 7

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C7 was used instead of the compound 1 in Example 1.

Comparative Example 8

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound C8 was used instead of the compound 1 in Example 1.

Comparative Example 9

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C9 was used instead of the compound 1 in Example 1.

Comparative Example 10

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C10 was used instead of the compound 1 in Example 1.

Comparative Example 11

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C11 was used instead of the compound 1 in Example 1.

Comparative Example 12

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C12 was used instead of the compound 1 in Example 1 above.

Comparative Example 13

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C13 was used instead of the compound 1 in Example 1.

Comparative Example 14

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C14 was used instead of the compound 1 in Example 1.

Comparative Example 15

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound C15 was used instead of the compound 1 in Example 1.

C1 to C15 are as follows.

The results of the organic light-emitting device fabricated in Examples 1 to 30 are shown in Table 1, and the results of the organic light-emitting device fabricated in Comparative Examples 1 to 15 are shown in Table 2. Voltage, efficiency, and emission color are data at 5000 nit brightness. The lifetime is 100% of the initial photocurrent value, and the time of 98% is indicated.

division matter The driving voltage (V) Efficiency (cd / A) Life span T98 (hr) Luminous color Example 1 Compound 1 3.70 47.8 173 Red Example 2 Compound 2 3.67 49.5 197 Red Example 3 Compound 3 3.77 46.7 165 Red Example 4 Compound 4 3.69 47.3 167 Red Example 5 Compound 5 3.70 44.8 131 Red Example 6 Compound 6 3.71 45.2 130 Red Example 7 Compound 7 3.82 45.3 150 Red Example 8 Compound 8 3.80 45.1 158 Red Example 9 Compound 9 3.78 44.1 187 Red Example 10 Compound 10 3.81 43.8 175 Red Example 11 Compound 11 3.80 44.7 141 Red Example 12 Compound 12 3.87 43.5 119 Red Example 13 Compound 13 3.89 41.6 110 Red Example 14 Compound 14 3.85 42.2 127 Red Example 15 Compound 15 3.84 43.1 151 Red Example 16 Compound 16 3.77 44.5 137 Red Example 17 Compound 17 3.78 45.4 149 Red Example 18 Compound 18 3.81 45.7 140 Red Example 19 Compound 19 3.77 50.3 179 Red Example 20 Compound 20 3.87 42.0 121 Red Example 21 Compound 21 3.73 44.8 131 Red Example 22 Compound 22 3.71 44.3 143 Red Example 23 Compound 23 3.77 45.0 148 Red Example 24 Compound 24 3.71 42.8 150 Red Example 25 Compound 25 3.77 43.8 141 Red Example 26 Compound 26 3.72 44.8 149 Red Example 27 Compound 27 3.79 46.2 134 Red Example 28 Compound 28 3.83 41.0 120 Red Example 29 Compound 29 3.76 45.8 151 Red Example 30 Compound 30 3.79 45.1 140 Red

division matter The driving voltage (V) Efficiency (cd / A) Life span T98 (hr) Luminous color Comparative Example 1 C1 4.35 25.1 18 Red Comparative Example 2 C2 4.40 20.3 13 Red Comparative Example 3 C3 4.51 24.7 14 Red Comparative Example 4 C4 4.53 21.7 17 Red Comparative Example 5 C5 4.37 20.5 20 Red Comparative Example 6 C6 4.39 19.8 19 Red Comparative Example 7 C7 4.08 40.3 41 Red Comparative Example 8 C8 4.13 40.1 45 Red Comparative Example 9 C9 4.17 38.8 37 Red Comparative Example 10 C10 4.20 39.7 38 Red Comparative Example 11 C11 4.24 38.4 35 Red Comparative Example 12 C12 4.35 35.7 71 Red Comparative Example 13 C13 4.30 36.1 60 Red Comparative Example 14 C14 4.27 37.0 55 Red Comparative Example 15 C15 4.24 36.0 40 Red

 As can be seen from the comparison of the results shown in Tables 1 to 2, the organic light emitting device using the compound of the present invention exhibits improved luminescence efficiency while lowering the driving voltage, and exhibits red light emission and improved lifetime. Since the comparative materials C1 to C6 have a wide energy band gap in comparison with the material of the present invention, energy transfer to the dopant in the red organic light emitting device is not performed well and the efficiency is low. Short results. In addition, the material of the present invention exhibits improvement in driving voltage and improvement of efficiency of about 0.4 V as compared with C7 to C15 materials which are mainly used in the light emitting layer in the related art, and more than four times (T98 standard) In the first half of the year.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7:
8: Electron transport layer

Claims (10)

A compound of formula
[Chemical Formula 1]

In Formula 1,
A is a 5-membered heterocyclic group containing O or S,
p is an integer of 0 to 4, and when p is 2 or more, Ar2 are the same or different from each other,
Ar1 is an aryl group which is substituted or unsubstituted with a deuterium, a nitrile group, an alkyl group, an aryl group or a heterocyclic group; Or a heterocyclic group substituted or unsubstituted with an aryl group,
Ar2 is hydrogen; An aryl group which is substituted or unsubstituted with deuterium, an alkyl group or a nitrile group; Or a heterocyclic group substituted or unsubstituted with an aryl group,
L is an arylene group; Or a divalent heterocyclic group,
n is 0 or 1,
R1 to R12 are each hydrogen. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or Formula 3:
(2)

(3)

In the general formula (2) or (3)
Ar1, Ar2, L, p, n and R1 to R12 are as defined in formula (1)
X is O or S; delete 2. The compound according to claim 1, wherein said formula (1) is selected from the following formulas:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1, 2 and 4 Lt; / RTI > The method of claim 5,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The method of claim 5,
Wherein the organic layer includes a light emitting layer, the light emitting layer includes the compound as a host material, and further includes another host material. The method of claim 5,
Wherein the organic layer includes a light emitting layer, the light emitting layer includes the compound, and further comprises a dopant compound. The method of claim 5,
Wherein the organic material layer includes an electron transporting layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, device. The method of claim 5,
Wherein the organic material layer includes a hole transporting layer, a hole injecting layer, or a layer simultaneously transporting holes and injecting holes, wherein the hole transporting layer, the hole injecting layer, or the layer that simultaneously transports holes and holes injects the organic light emitting device.

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