KR20180106234A - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a hetero-cyclic compound represented by chemical formula 1, and an organic light emitting device comprising the same. The compound according to at least one embodiment of the present invention can improve the efficiency, the driving voltage and/or the lifetime of the organic light emitting device.

Description

[0001] HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, the electrons injected from the two electrodes and the electrons combine in the organic thin film to form a pair, and then the light is emitted while disappearing. The organic thin film may be composed of a single layer or a multilayer, if necessary.

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 state in oxidation and in a reduced state is preferable, and an exciton formed by recombination of holes and electrons in the light emitting layer is formed It is preferable to use a material having a high luminous efficiency for converting it into light.

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

Japanese Patent Application Laid-Open No. 2015-221780

The present invention provides a heterocyclic compound and an organic light emitting device including the heterocyclic compound.

According to one embodiment of the present invention, there is provided a heterocyclic compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a ring,

R5 to R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring,

W and X are the same or different from each other and each independently O, S, Se, Be, NQ ₁ , PQ ₂ , SO, SO ₂ , PO, SiQ ₃ Q ₄ or CQ ₅ Q ₆ ,

Y and Z are the same as or different from each other, and each independently represents O, S, Se, Be, NRa, PRb, SO, SO _2, PO, SiRcRd, CReRf, and CRgRh-CRiRj, CRk = CRl, CRm = N or PORn ,

Q ₁ to ₆ Q, Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, Rl and Rm Rn is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n1 and n2 are each 1 or 2,

a and b are each 0 or 1,

c and e are each an integer of 0 to 4,

d is an integer of 0 to 2,

When n1, n2 and d are each 2, the substituents in the parentheses are the same or different from each other,

When c and e are each 2 or more, the substituents in the parentheses are the same or different from each other.

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: 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 a heterocyclic compound represented by Formula 1, Lt; / RTI >

The heterocyclic compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. The compound described in this specification can be used as a material for the hole injecting layer, the hole transporting layer, the hole injecting layer and the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer, or the electron injecting layer.

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 3, an electron transporting layer 7 and a cathode 4 It is.

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

The present invention provides a heterocyclic compound represented by the above formula (1). When the heterocyclic compound represented by the formula (1) is used for an organic material layer of an organic light emitting device, the efficiency of the organic light emitting device is not only always low, but also has a low driving voltage and excellent lifetime characteristics.

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 herein are described below, but are not limited thereto.

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. 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 or may be interpreted as a substituent in which two phenyl groups are connected.

In this specification, "adjacent" The group may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom of the substituent. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.

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

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c 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 -BR _a R _b , wherein R _a and R _b 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, the number of carbon atoms of the alkylamine group is not particularly limited, but is preferably 1 to 40. Specific examples of the alkylamine 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, Group, 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, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 40 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, An n-pentyl group, a tert-butyl group, a tert-butyl group, a 3-methylbutyl group, a 3-methylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.

In the present 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 40 carbon atoms. According to another embodiment, the number of carbon atoms in the cycloalkyl group is from 1 to 20. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. 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 the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 60 carbon atoms. According to one embodiment, the aryl group has 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 60 carbon atoms. According to one embodiment, the aryl group has 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

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, P, S, Si and Se, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is from 1 to 30. [ Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, a thiazolidinyl group, a thiomorpholinyl group, a thiomorpholinyl group, a thiomorpholinyl group, an isothiazolyl group, , Indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl , A carbazole group, a benzocarbazole group, a dibenzocarbazole group, an indolocarbazole group, an indenocarbazole group, a phenazinyl group, an imidazopyridine group, a phenoxazinyl group, a phenanthroline group, a phenanthroline group, Phenothiazine group, imidazopyridine group, imidazophenanthridine group. A benzoimidazoquinazolinyl group, a benzoimidazophenanthridin group, and the like, but are not limited thereto.

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

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.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.

In the present specification, the explanation about the aryl group except for the monovalent aromatic hydrocarbon ring can be applied.

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the examples of the heterocyclic group except that the heterocyclic group is not monovalent.

In the present specification, the heterocyclic compound represented by the above formula (1) is provided.

In one embodiment of the present specification, W and X are the same or different from each other and each independently represents O, S, Se, Be, NQ ₁ , PQ ₂ , SO, SO ₂ , PO, SiQ ₃ Q _{4, 5} Q ₆ .

In another embodiment, W and X are the same or different and are each independently 0, S, P = O, NQ ₁ or CQ ₅ Q ₆ .

According to another embodiment, W and X are the same or different and each independently O, S or P = O.

In another embodiment, W and X are the same or different and are each independently O or S.

In another embodiment, W and X are O.

In one embodiment of the present disclosure, Q ₁ is selected from the group consisting of hydrogen; Deuterium, or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, Q ₁ is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment Q ₁ is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Q ₁ is a substituted or unsubstituted phenyl group.

In another embodiment, Q ₁ is a phenyl group.

In one embodiment of the present specification, Q < ₂ > is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present disclosure, wherein Q ₂ is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

Further in one exemplary embodiment of the Q ₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Q < ₂ > is a substituted or unsubstituted phenyl group.

In another embodiment, Q < ₂ > is a phenyl group.

In one embodiment of the present specification, Q ₃ and Q ₄ are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, Q ₃ and Q ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Q ₃ and Q ₄ are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Q ₃ and Q ₄ are a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

According to another embodiment, Q ₃ and Q ₄ are a methyl group or a phenyl group.

In one embodiment of the present specification, Q ₅ and Q ₆ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present disclosure, the Q ₅ and Q ₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Q ₅ and Q ₆ are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Q ₅ and Q ₆ are a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

Further in one exemplary embodiment of the Q ₅ and Q ₆ is a methyl group or a phenyl group.

In one embodiment of the present invention, the formula (1) is represented by the following formula (2).

(2)

In Formula 2,

The definitions of R1 to R9, Z, Y, n1, n2 and a to e are as defined in the above formula (1).

In one embodiment of the present disclosure, n1 and n2 are one.

In another embodiment, n1 and n2 are two.

In one embodiment of the present invention, R 1 to R 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

In one embodiment of the present invention, R 1 to R 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group, or adjacent substituents are bonded to each other to form a ring.

According to another embodiment, R 1 to R 4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent substituents are bonded to each other to form a ring.

According to another embodiment, R 1 to R 4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or adjacent substituents are bonded to each other to form a ring.

According to another embodiment, R 1 to R 4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In another embodiment, R 1 to R 4 are substituted or unsubstituted phenyl groups.

In one embodiment of the present specification, R 1 and R 2 are bonded to each other to form a substituted or unsubstituted heterocycle.

In another embodiment, R 1 and R 2 combine with each other to form an aromatic heterocyclic ring.

In another embodiment, R 1 and R 2 are bonded to each other to form a substituted or unsubstituted carbazolyl group.

In one embodiment of the present specification, R 3 and R 4 are bonded to each other to form a substituted or unsubstituted heterocycle.

In another embodiment, R 3 and R 4 combine with each other to form an aromatic heterocycle.

According to one embodiment of the present invention, R 3 and R 4 are bonded to each other to form a substituted or unsubstituted carbazolyl group.

In one embodiment of the present invention, the formula (1) is represented by the following formula (3) or (4).

(3)

[Chemical Formula 4]

In the above formulas (3) and (4)

R5 to R9, W, X, Z, Y and a to e are as defined in the above formula (1)

Ar 1 to Ar 6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring,

m1 to m4 each represent an integer of 0 to 5,

m5 and m6 are each an integer of 0 to 8,

When m1 to m6 are each 2 or more, the substituents in the parentheses are the same or different from each other.

In one embodiment of the present invention, the formula (1) is represented by the following formula (5) or (6).

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas (5) and (6)

R5 to R9, Z, Y and a to e are as defined in the above formula (1)

Ar 1 to Ar 6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring,

m1 to m4 each represent an integer of 0 to 5,

m5 and m6 are each an integer of 0 to 8,

When m1 to m6 are each 2 or more, the substituents in the parentheses are the same or different from each other.

In one embodiment of this disclosure, the Y and Z are the same as or different from each other, each independently represent O, S, Se, Be, NRa, PRb, SO, SO _2, PO, SiRcRd, CReRf, CRgRh-CRiRj, CRk = CRl, CRm = N or PORn.

According to one exemplary embodiment of the Y and Z are the same as or different from each other, each independently represent O, S, NRa, PRb, SO, SO _2, SiRcRd, or CReRf PORn.

In one embodiment of the present disclosure, Y and Z are O.

In one embodiment of the present disclosure, Y and Z are S.

In one embodiment of the present disclosure, Y and Z are CReRf.

In one embodiment of the present specification, Re and Rf are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, Re and Rf are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Re and Rf are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Re and Rf are substituted or unsubstituted methyl groups.

According to another embodiment, Re and Rf are methyl groups.

In one embodiment of the present disclosure, Y and Z are SiRcRd.

In one embodiment of the present specification, Rc and Rd are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present disclosure, Rc and Rd are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Rc and Rd are substituted or unsubstituted methyl groups.

According to another embodiment, Rc and Rd are methyl groups.

In one embodiment of the present disclosure, Y and Z are SO.

In one embodiment of the present disclosure, Y and Z are NRa.

In one embodiment of the present disclosure, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

In another embodiment, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Ra is a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In another embodiment, Ra is a phenyl group.

In one embodiment of the present disclosure, Y and Z are PRb.

In one embodiment of the present specification, R < b > is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to one embodiment of the present invention, Rb are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, the R < b > s are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

In another embodiment, the R < b > s are the same or different and independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Rb is a substituted or unsubstituted phenyl group.

In another embodiment, Rb is a phenyl group.

의 구조를 갖는 것을 의미하며, '

'는 화학식 1의 연결되는 부위를 의미한다.In one embodiment of the present disclosure, Y and Z are PORn, PORn is -P (= O) Rn-,

&Quot; and "

&Quot; means a linked site of formula (1).

In one embodiment of the present disclosure, Rn is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another embodiment, Rn is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Rn is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 12 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

According to another embodiment, Rn is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted ethyl group.

According to another embodiment, Rn is a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

According to another embodiment, Rn is a phenyl group.

의 구조를 갖는 것을 의미하며, '

'는 화학식 1의 연결되는 부위를 의미한다.In one embodiment of the present disclosure, Y and Z are SO ₂ , SO ₂ is

&Quot; and "

&Quot; means a linked site of formula (1).

In one embodiment of the present specification, one of Y and Z is O and the other is S.

In one embodiment of the present specification, one of Y and Z is O and the other is CReRf.

In one embodiment of the present specification, one of Y and Z is O and the other is NRa.

In one embodiment of the present specification, one of Y and Z is S and the other is NRa.

In one embodiment of the present specification, Rg, Rh, Ri, Rj, Rk, Rl and Rm are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In another embodiment, Rg, Rh, Ri, Rj, Rk, Rl and Rm are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another embodiment, Rg, Rh, Ri, Rj, Rk, Rl and Rm are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another embodiment, Rg, Rh, Ri, Rj, Rk, Rl and Rm are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted C6 to C20 aryl group.

In another embodiment, Rg, Rh, Ri, Rj, Rk, Rl and Rm are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another embodiment, Rg, Rh, Ri, Rj, Rk, Rl and Rm are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Methyl group; An ethyl group; Propyl group; A phenyl group; A biphenyl group; Or a naphthyl group.

In one embodiment of the present specification, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In another embodiment, R5 and R6 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In another embodiment, R5 and R6 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 12 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; Or a substituted or unsubstituted C2-C20 heterocyclic group.

In another embodiment, R5 and R6 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted C6 to C12 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 12 carbon atoms.

According to another embodiment, R5 and R6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted phenyl group.

According to another embodiment, R5 and R6 are hydrogen or a substituted or unsubstituted methyl group.

According to one embodiment of the present disclosure, a and b are one.

In one embodiment of the present specification, c and e are an integer of 0 to 2.

In one embodiment of the present disclosure, c and e are two.

In one embodiment of the present disclosure, c and e are one.

In one embodiment of the present disclosure, c and e are zero.

In one embodiment of the present specification, R7 and R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

In another embodiment, R7 and R9 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent substituents are bonded to each other to form a ring.

In another embodiment, R7 and R9 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted C2-C20 heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

In another embodiment, R7 and R9 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 12 carbon atoms; A substituted or unsubstituted C6 to C12 aryl; A substituted or unsubstituted arylamine group; Or a substituted or unsubstituted C2-C12 heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

In another embodiment, R7 and R9 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted diphenylamine group, or adjacent substituents are bonded to each other to form a ring.

In another embodiment, R7 and R9 are independently selected from the group consisting of hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted diphenylamine group.

In another embodiment, R7 and R9 are independently selected from the group consisting of hydrogen; A phenyl group; Or a diphenylamine group.

In another embodiment, in the case where c is 2 or more, adjacent R < 7 > may bond to each other to form a ring.

In another embodiment, in the case where c is 2 or more, adjacent R 7 may combine with each other to form a hydrocarbon ring.

According to another embodiment, when c is 2 or more, adjacent R < 7 > may combine with each other to form an aromatic hydrocarbon ring.

According to another embodiment, when c is 2 or more, adjacent R < 7 > may combine with each other to form a benzene ring.

In another embodiment, in the case where e is 2 or more, adjacent R9 may combine with each other to form a ring.

In another embodiment, when e is 2 or more, adjacent R9 may combine with each other to form a hydrocarbon ring.

According to another embodiment, in the case where e is 2 or more, adjacent R9 may combine with each other to form an aromatic hydrocarbon ring.

According to another embodiment, in the case where e is 2 or more, adjacent R9 may combine with each other to form a benzene ring.

In one embodiment of the present disclosure, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

In another embodiment, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A nitrile group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent substituents are bonded to each other to form a ring.

In another embodiment, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A nitrile group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; Or a substituted or unsubstituted C2-C20 heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

In another embodiment, R8 is selected from the group consisting of hydrogen; heavy hydrogen; A nitrile group; A substituted or unsubstituted alkyl group having 1 to 12 carbon atoms; A substituted or unsubstituted C6 to C12 aryl; Or a substituted or unsubstituted C2-C12 heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

In another embodiment R8 is hydrogen or a nitrile group.

In another embodiment, when d is 2, adjacent R 8 may combine with each other to form a ring.

In another embodiment, when d is 2, adjacent R 8 may combine with each other to form a hydrocarbon ring.

According to another embodiment, when d is 2, adjacent R < 8 > may combine with each other to form an aromatic hydrocarbon ring.

According to another embodiment, when d is 2, adjacent R 8 may combine with each other to form a benzene ring.

In one embodiment of the present specification, Ar1 to Ar4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent substituents are bonded to each other to form a ring.

According to one embodiment of the present invention, Ar1 to Ar4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; Or a substituted or unsubstituted C2-C20 heterocyclic group, or adjacent substituents are bonded to each other to form a ring.

According to another embodiment, Ar1 to Ar4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted t-butyl group or an adjacent substituent is bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted aromatic heterocycle.

According to another embodiment, Ar1 to Ar4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted t-butyl group or an adjacent substituent is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted aromatic heterocycle.

According to one embodiment of the present invention, m1 to m4 are integers of 0 to 2, respectively.

According to one embodiment of the present invention, when m1 is 2, adjacent Ar1 may combine with each other to form a ring.

In another embodiment, when m1 is 2, adjacent Ar1 may combine with each other to form a hydrocarbon ring.

According to another embodiment, when m1 is 2, adjacent Ar1 may combine with each other to form an aromatic hydrocarbon ring.

According to another embodiment of the present invention, when m1 is 2 or more, adjacent Ar1 may combine with each other to form a benzene ring to form a naphthyl group.

In another embodiment, when m1 is 2, adjacent Ar1 may combine with each other to form a heterocycle.

According to another embodiment, when m1 is 2, adjacent Ar1 may combine with each other to form an aromatic heterocyclic ring.

According to another embodiment, when m1 is 2, adjacent Ar1 may combine with each other to form a benzofuran ring to form a dibenzofuranyl group.

According to one embodiment of the present invention, when m2 is 2, adjacent Ar2 may combine with each other to form a ring.

In another embodiment, when m2 is 2, adjacent Ar2 may combine with each other to form a hydrocarbon ring.

According to another embodiment, in the case where m2 is 2, adjacent Ar2 may combine with each other to form an aromatic hydrocarbon ring.

According to another embodiment, when m2 is 2, adjacent Ar2 may combine with each other to form a benzene ring to form a naphthyl group.

In another embodiment, when m2 is 2, adjacent Ar2 may combine with each other to form a heterocycle.

According to another embodiment, in the case where m2 is 2, adjacent Ar2 may combine with each other to form an aromatic heterocyclic ring.

According to another embodiment, when m2 is 2, adjacent Ar2 may combine with each other to form a benzofuran ring to form a dibenzofuranyl group.

According to one embodiment of the present invention, when m3 is 2, adjacent Ar3 may combine with each other to form a ring.

In another embodiment, when m3 is 2, adjacent Ar3 may combine with each other to form a hydrocarbon ring.

According to another embodiment, when m3 is 2, adjacent Ar3 may combine with each other to form an aromatic hydrocarbon ring.

According to another embodiment, when m3 is 2, adjacent Ar3 may combine with each other to form a benzene ring to form a naphthyl group.

In another embodiment, when m3 is 2, adjacent Ar3 may combine with each other to form a heterocycle.

According to another embodiment, when m3 is 2, adjacent Ar3 may combine with each other to form an aromatic heterocycle.

According to another embodiment, when m3 is 2, adjacent Ar3 may combine with each other to form a benzofuran ring to form a dibenzofuranyl group.

According to one embodiment of the present invention, when m4 is 2, adjacent Ar4 may combine with each other to form a ring.

In another embodiment, when m4 is 2, adjacent Ar4 may combine with each other to form a hydrocarbon ring.

According to another embodiment, when m4 is 2, adjacent Ar4 may combine with each other to form an aromatic hydrocarbon ring.

According to another embodiment, when m4 is 2, adjacent Ar4 may combine with each other to form a benzene ring to form a naphthyl group.

In another embodiment, when m4 is 2, adjacent Ar4 may combine with each other to form a heterocycle.

According to another embodiment, when m4 is 2, adjacent Ar4 may combine with each other to form an aromatic heterocycle.

According to another embodiment, when m4 is 2, adjacent Ar4 may combine with each other to form a benzofuran ring to form a dibenzofuranyl group.

In one embodiment of the present specification, Ar1 and Ar2; And at least one or more of Ar3 and Ar4 may combine with each other to form a ring.

In one embodiment of the present invention, Ar1 and Ar2 may combine with each other to form a ring.

In one embodiment of the present specification, Ar1 and Ar2 may be connected to S, O or CX1X2 to form a hexagonal ring.

In one embodiment of the present specification, X1 and X2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In another embodiment, X1 and X2 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; Or the substituent is an unsubstituted alkyl group having 1 to 12 carbon atoms.

In another embodiment, X1 and X2 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted ethyl group.

In another embodiment, X1 and X2 are the same or different and are each independently a substituted or unsubstituted methyl group.

In another embodiment, X1 and X2 are methyl groups.

In one embodiment of the present specification, Ar3 and Ar4 may be linked to S, O or CX3X4 to form a ring.

In one embodiment of the present specification, X3 and X4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In another embodiment, X3 and X4 are the same or different and each independently hydrogen; heavy hydrogen; Or the substituent is an unsubstituted alkyl group having 1 to 12 carbon atoms.

In another embodiment, X3 and X4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; Or a substituted or unsubstituted ethyl group.

In another embodiment, X3 and X4 are the same or different and are each independently a substituted or unsubstituted methyl group.

In another embodiment, X3 and X4 are methyl groups.

In one embodiment of the present specification, Ar5 and Ar6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar5 and Ar6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar5 and Ar6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C6 to C20 aryl; Or a substituted or unsubstituted C2-C20 heterocyclic group.

In another embodiment, Ar5 and Ar6 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In another embodiment, Ar5 and Ar6 are the same or different and are each independently selected from the group consisting of hydrogen; heavy hydrogen; Methyl group; An ethyl group; A phenyl group; Or a biphenyl group.

In another embodiment, Ar5 and Ar6 are the same or different and each independently hydrogen or a methyl group.

In one embodiment of the present specification, m5 and m6 are integers of 0 to 2, respectively.

In another embodiment, m5 and m6 are 0 or 1.

In one embodiment of the present invention, the core structure of Formula 1 may have the following structure, and the core structure may include a substituent ((NR1R2) n1, (NR3R4) n2, (R5) R6) b, (R7) c, (R8) d, (R9) e).

In one embodiment of the present invention, the heterocyclic compound of Formula 1 may be any one selected from the following compounds.

The compound according to one embodiment of the present specification can be produced by a production method described below.

For example, the heterocyclic compound of Formula 1 may have a core structure as shown in the following reaction formula. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents into the core structure as described above. Further, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents to the core structure having the above structure.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Further, the organic light emitting device according to the present invention 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 heterocyclic compound of Formula 1.

The organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.

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

The organic 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 the organic light emitting device of the present invention, the organic material layer may include at least one of an electron transporting layer, an electron injecting layer, and a layer simultaneously performing electron injection and electron transporting, and at least one of the layers may be represented by Formula 1 Heterocyclic compounds.

In another organic light emitting device, the organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer may include a heterocyclic compound represented by the above formula (1).

In the organic light emitting device of the present invention, the organic material layer may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, and at least one of the layers may be represented by Formula 1 Heterocyclic compounds.

In another organic light emitting device, the organic material layer may include a hole injecting layer or a hole transporting layer, and the electron transporting layer or the electron injecting layer may include a heterocyclic compound represented by the above formula (1).

In another embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a heterocyclic compound represented by the general formula (1). As one example, the compound represented by Formula 1 may be included as a dopant in the light emitting layer.

As another example, the organic compound layer containing the heterocyclic compound represented by Formula 1 may include a compound represented by Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host.

In another embodiment, the organic compound layer containing the heterocyclic compound represented by the formula (1) contains the compound represented by the formula (1) as a dopant and includes a fluorescent host or a phosphorescent host, A metal compound may be contained as a dopant.

As another example, the organic material layer containing the heterocyclic compound represented by Formula 1 may include a compound represented by Formula 1 as a dopant, a fluorescent host or a phosphorescent host, and may include an iridium (Ir) Can be used.

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

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, or the electron transporting layer 7.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon. In addition to such a method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

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-methyl compounds), poly [3,4- (ethylene-1,2-dioxy) compounds] (PEDT), 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.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is 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 porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes 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 layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material. 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.

Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. 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.

The iridium complex used as a dopant in the light emitting layer is as follows but is not limited thereto.

[Ir (piq) ₃ ] [Btp ₂ Ir (acac)]

[Ir (ppy) ₃ ] [Ir (ppy) ₂ (acac)]

[Ir (mpyp) ₃ ] [F ₂ Irpic]

[(F ₂ ppy) ₂ Ir (tmd)] [Ir (dfppz) ₃ ]

　　　

　　　

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. 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 organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

< Manufacturing example >

1. Preparation of compound 1

1) Preparation of intermediate 1

                                        Intermediate 1

After dissolving 1-chloro-3,5-dimethoxybenzene (10.0 g, 58 mmol) and N -bromosuccinimide (10.3 g, 58 mmol) in 1,2-diethylene chloride (200 ml) Lt; / RTI &gt; for 24 hours. After completion of the reaction, the reaction solution was subjected to rotary evaporation to remove the solvent, followed by extraction with methylene chloride / distilled water and column chromatography using a developing solvent of methylene chloride / hexane as an eluent to obtain 13.3 g of Intermediate 1.

Intermediate 1: yield 91%, Mass Spec (EI) m / z 251 [ (M + H) +], 1 H NMR (500 MHz, CDCl 3): δ 6.57 (s, 1H), 6.26 (s, 1H) , 3.81 (s, 3 H), 3.69 (s, 3 H).

2) Preparation of intermediate 2

                                                   Intermediate 2

A mixture of Intermediate 1 (4.5 g, 18.1 mmol), 2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (4 g, 18.1 mmol), tetrakis Triphenylphosphine) palladium (0) (0.9 g, 0.9 mmol) was added to a mixture of tetrahydrofuran (60 ml) and potassium carbonate 2M solution (20 ml) and refluxed for 24 hours. After completion of the reaction, the reaction solution was extracted with methylene chloride, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as a developing solvent. After final drying, 4.8 g of intermediate 2 were obtained.

Intermediate 2: yield 84%, Mass Spec (EI) m / z 263 [ (M + H) +], 1 H NMR (500 MHz, CDCl 3): δ 7.54 (d, 1H), 7.16 (t, 1H) , 6.87 (s, 3H), 6.82 (s, 3H), 6.87 (s, 1H).

3) Preparation of intermediate 3

                                                  Intermediate 3

Intermediate 2 (5 g, 22.6 mmol) is dissolved in tetrahydrofuran (25 ml) and acetic acid (50 ml) is added to prepare a reaction solution. After the temperature of the reaction solution was lowered to -10 ° C, tert -butyl nitrite (2.3 g, 22.6 mmol) was slowly added thereto and stirred for 1 hour. After 1 hour, the temperature is slowly raised to 0 &lt; 0 &gt; C and then stirred for another 12 hours. After the reaction was completed, the reaction solution was extracted with methylene chloride, and then subjected to column chromatography using a methylene chloride / hexane mixed solvent as eluent to obtain 3.5 g of Intermediate 3.

Intermediate 3: yield 67%, Mass Spec (EI) m / z 232 [ (M + H) +], 1 H NMR (500 MHz, CDCl 3): δ 8.24 (d, 1H), 7.52 (d, 1H) , 7.42 (t, 1 H), 7.36 (t, 1 H), 7.01 (s, 1 H), 6.95 (1s, 1 H).

4) Preparation of intermediate 4

                                                  Intermediate 4

Intermediate 3 (5 g, 21.5 mmol) was dissolved in tetrahydrofuran (25 ml), and then 2.5 M n -butyllithium (9 ml, 22.5 mmol) was slowly added under nitrogen at -78 ° C. After stirring for 1 hour, triisopropylborate (3.3 g, 23.65 mmol) was added to the reaction solution and stirred for 3 hours. After the reaction was completed, the reaction solution was extracted with a 5% aqueous hydrochloric acid solution and methylene chloride, and then subjected to column chromatography using a developing solvent of ethyl acetate / hexane as a developing solvent to obtain 2.8 g of Intermediate 4.

Intermediate 4: yield 52%, Mass Spec (EI) m / z 276 [ (M + H) +], 1 H NMR (500 MHz, CDCl 3): δ 7.89 (d, 1H), 7.66 (d, 1H) , 7.38-7.32 (m, 2H), 6.96 (s, IH), 3.83 (s, 3H).

5) Preparation of intermediate 5

                                                 Intermediate 5

A solution of intermediate 4 (5 g, 18.1 mmol), 1,4-dibromo-2,3-difluorobenzene (2.4 g, 9.0 mmol), tetrakis (triphenylphosphine) palladium (0) mmol) is added to a mixed solvent of tetrahydrofuran (60 ml) and potassium carbonate 2M solution (20 ml), and the mixture is refluxed for 24 hours. After the reaction was completed, the reaction solution was extracted with methylene chloride, and then subjected to column chromatography using a solvent mixture of methylene chloride / hexane as a developing solvent to obtain 4.3 g of Intermediate 5.

Intermediate 5: yield 83%, Mass Spec (EI) m / z 574 [ (M + H) +], 1 H NMR (500 MHz, CDCl 3): δ 7.89 (d, 2H), 7.66 (d, 2H) , 7.60 (d, 2H), 7.38-7.32 (m, 4H), 6.71 (s, 2H), 3.83 (s, 6H).

6) Preparation of intermediate 6

                                                 Intermediate 6

Intermediate 5 (5 g, 8.7 mmol) was dissolved in dichloromethane (100 ml), boron tribromide (2.2 g, 8.7 mmol) was slowly added at 0 ° C and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, the reaction solution was extracted with methylene chloride, and then subjected to column chromatography using an ethyl acetate / hexane mixed solvent as a developing solvent to obtain 3.4 g of Intermediate 6.

Intermediate 6: yield 72%, Mass Spec (EI) m / z 546 [ (M + H) +], 1 H NMR (500 MHz, CDCl 3): δ 10.3 (s, 2H), 7.89 (d, 2H) , 7.66 (d, 2H), 7.60 (d, 2H), 7.38-7.22 (m, 4H), 6.67 (s, 2H).

7) Preparation of intermediate 7

                                                 Intermediate 7

Intermediate 6 (5 g, 9.1 mmol) and potassium carbonate (2.5 g, 18.2 mmol) were dissolved in N -methyl-2-pyrrolidone (70 ml) and reacted at 150 ° C for 12 hours. After the reaction was completed, the reaction solution was extracted with ethyl acetate and the solvent was removed to obtain 3.6 g of Intermediate 7.

Intermediate 7: yield 78%, Mass Spec (EI) m / z 506 [ (M + H) +], 1 H NMR (500 MHz, CDCl 3): δ 7.89 (d, 2H), 7.71 ~ 7.66 (m, 4H), 7.43-7.32 (m, 6H).

8) Preparation of compound 1

                                                  Compound 1

(3.4 g, 19.7 mmol), tri- tert -butylphosphine (0.4 g, 2.0 mmol), sodium tert -butoxide (2 g, 21.7 mmol), palladium acetate 0.3 g, 0.9 mmol) was dissolved in 1,2-dichlorobenzene (100 ml), and the mixture was refluxed under nitrogen for 24 hours. After the completion of the reaction, the reaction solution was extracted with methylene chloride, and then subjected to column chromatography using a methylene chloride / hexane mixed solvent as a developing solvent to obtain 5.4 g of Compound 1.

Compound 1: yield 71%, mass spectrometry (FAB) m / z 772 [(M + H) ⁺ ], ¹ H NMR (500 MHz, CDCl ₃ ):? 7.89 4H), 7.43-7.32 (m, 6H), 7.20 (t, 8H), 6.81 (t, 4H), 6.63 (d, 8H).

2. Preparation of compound 2

                                                   Compound 2

The reaction was carried out in the same manner as in the synthesis of Compound 1, except that diphenylamine was replaced with bis (4- ( tert -butyl) phenyl) amine to obtain 7.5 g of Compound 2. [

Compound 2: Yield 76%, mass spectrometry (FAB) m / z 996 [(M + H) ⁺ ], ¹ H NMR (500 MHz, CDCl ₃ ):? 7.89 4H), 7.43-7.22 (m, 6H), 7.01 (d, 8H), 6.55 (d, 8H), 1.35 (s, 36H).

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

Claims (8)

A heterocyclic compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent substituents are bonded to each other to form a ring,
R5 to R9 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring,
W and X are the same or different from each other and each independently O, S, Se, Be, NQ ₁ , PQ ₂ , SO, SO ₂ , PO, SiQ ₃ Q ₄ or CQ ₅ Q ₆ ,
Y and Z are the same as or different from each other, and each independently represents O, S, Se, Be, NRa, PRb, SO, SO _2, PO, SiRcRd, CReRf, and CRgRh-CRiRj, CRk = CRl, CRm = N or PORn ,
Q ₁ to ₆ Q, Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri, Rj, Rk, Rl and Rm Rn is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
n1 and n2 are each 1 or 2,
a and b are each 0 or 1,
c and e are each an integer of 0 to 4,
d is an integer of 0 to 2,
When n1, n2 and d are each 2, the substituents in the parentheses are the same or different from each other,
When c and e are each 2 or more, the substituents in the parentheses are the same or different from each other. The compound of claim 1, wherein the compound represented by Formula 1 is a heterocyclic compound represented by Formula 2:
(2)

In Formula 2,
The definitions of R1 to R9, Z, Y, n1, n2 and a to e are as defined in the above formula (1). [3] The compound according to claim 1, wherein the formula 1 is a heterocyclic compound represented by the following formula 3 or 4:
(3)

[Chemical Formula 4]

In the above formulas (3) and (4)
R5 to R9, W, X, Z, Y and a to e are as defined in the above formula (1)
Ar 1 to Ar 6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring,
m1 to m4 each represent an integer of 0 to 5,
m5 and m6 are each an integer of 0 to 8,
When m1 to m6 are each 2 or more, the substituents in the parentheses are the same or different from each other. 2. The heterocyclic compound according to claim 1, wherein the compound represented by Formula 1 is a heterocyclic compound represented by Formula 5 or 6:
[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas (5) and (6)
R5 to R9, Z, Y and a to e are as defined in the above formula (1)
Ar 1 to Ar 6 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylamine group, or adjacent substituents are bonded to each other to form a ring,
m1 to m4 each represent an integer of 0 to 5,
m5 and m6 are each an integer of 0 to 8,
When m1 to m6 are each 2 or more, the substituents in the parentheses are the same or different from each other. 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 includes the heterocyclic compound according to any one of claims 1 to 4 Lt; / RTI &gt; The method of claim 5,
Wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the heterocycle compound of Formula 1. The method of claim 5,
Wherein the organic material layer comprises an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer comprises the heterocyclic compound of the formula (1). The method of claim 5,
Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound of Formula 1.

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