KR20160026737A - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a heterocyclic compound, and an organic light emitting device comprising the same. The heterocyclic compound is represented by chemical formula 1. The compound can improve efficiency and/or lifespan properties in the organic light emitting device.

Description

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

This specification claims the benefit of Korean Patent Application No. 10-2014-0114486 filed on August 29, 2014, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

Korean Patent Publication No. 2000-0051826

Heterocyclic compounds and organic light emitting devices containing them are described in this specification.

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

[Chemical Formula 1]

In Formula 1,

X is _{NR 1, CR 2 R 3,} SiR 4 R 5, S or O,

L are the same or different and are each independently a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,

Y is CN, P (= O) Ar 1 Ar 2, or SO ₂ Ar _3,

Ar ₁ and Ar ₂ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar ₃ is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; Or a substituted or unsubstituted aryl group,

R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or is bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

R ₁₃ , R ₁₄ and R ₁₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,

R ₁₁ And R < ₁₂ > are the same or different from each other, and each independently hydrogen; heavy hydrogen; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

n, p and q are the same or different and each is an integer of 1 to 4,

m, r and s are the same or different and each is an integer of 1 to 3,

when n is 2 or more, R < ₁₁ > are the same or different from each other,

When m is 2 or more, R ₁₂ are the same or different from each other,

When p is 2 or more, R ₁₃ are the same or different from each other,

If there is more than q is 2 R ₁₄ is the same as or different from each other, and

When r is 2 or more, R < ₁₅ >

When s is 2 or more, L is the same or different from each other.

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 heterocyclic compound of Formula 1 do.

The 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, the lower the driving voltage and / or the lifetime characteristics in the organic light emitting device. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting materials.

The compound according to the present invention can be used as a phosphorescent host of the light emitting layer. Conventional compounds having a carbazole skeleton have a property of transporting positive charges of electrons and holes, but their electron transport ability is lower than that of holes. It is expected that the charge balance in the light emitting layer can be enhanced by introducing an aryl compound having a substituent serving as an electron acceptor such as a nitrile group, a phosphine oxide group and a sulfone group in order to increase the electron transporting ability to the carbazole skeleton. This can contribute to improvement of the efficiency and / or lifetime of the device.

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 shows MS data of the compound 1-1.
Figure 4 shows MS data for compound 1-90.
5 shows the MS data of Compound 1-73

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 the present specification,

Quot; means a bond connected to another substituent.

Illustrative examples of such substituents are set forth 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 amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; 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; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . For example, the "substituent group to which two or more 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.

As used herein, the term "adjacent" means that the substituent is 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 . 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 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 silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, 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, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

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 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 and a fluorenyl 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.

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 hetero ring group containing at least one of O, N, Si and S as a hetero atom, and 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, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.

In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above.

In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group.

In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.

In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group.

In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.

In the present specification, the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monocyclic and the two substituents are bonded to each other.

In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (6).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above Formulas 2 to 6,

The definitions of Y, L, R ₁ to R ₅ , R ₁₁ to R ₁₅ , n, m, p, q, r and s are as shown in formula (1).

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (7) to (9).

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas (7) to (9)

The definitions of Y, L, R ₁ to R ₅ , R ₁₁ to R ₁₅ , n, m, p, q, r and s are as shown in formula (1).

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (10).

[Chemical formula 10]

In Formula 10,

Y, R ₁ to R ₅ , R ₁₁ to R ₁₅ , n, m, p, q and r are as defined in formula (1).

According to one embodiment of the present invention, the formula (1) may be represented by the following formula (11).

(11)

In Formula 11,

Y, R ₁ to R ₅ , R ₁₁ to R ₁₅ , n, m, p, q and r are as defined in formula (1).

According to one embodiment of the present disclosure, L is substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene.

According to one embodiment of the present disclosure, L is substituted or unsubstituted phenylene; Substituted or unsubstituted fluorenylenes; Or heteroarylene containing at least one substituted or unsubstituted S;

According to one embodiment of the present disclosure, L is phenylene; Fluorenylene substituted with an alkyl group; Or a heteroarylene comprising at least one S;

According to one embodiment of the present disclosure, L is phenylene; Fluorenylene substituted with an alkyl group; Or dibenzothiophene.

According to one embodiment of the present disclosure, L is phenylene; Fluorenylene substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms; Or dibenzothiophene.

According to one embodiment of the present disclosure, L is phenylene; Fluorenylene substituted with an alkyl group having 1 to 5 carbon atoms; Or dibenzothiophene.

According to one embodiment of the present disclosure, L is fluorenylene substituted with an alkyl group.

According to one embodiment of the present disclosure, L is dibenzothiophene.

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

According to one embodiment of the present disclosure, R ₁ is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, R ₁ is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to one embodiment of the present invention, R ₁ is a substituted or unsubstituted phenyl group.

According to one embodiment of the present disclosure, R ₁ is a phenyl group.

According to one embodiment of the present invention, R ₂ and R ₃ are the same or different and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a ring.

According to one embodiment of the present invention, R ₂ and R ₃ are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a substituted or unsubstituted phenyl group, or are bonded to each other to form a substituted or unsubstituted fluorene.

According to one embodiment of the present invention, R ₂ and R ₃ are the same or different and each independently is an alkyl group having 1 to 6 carbon atoms; Or a phenyl group, or combine with each other to form fluorene, dimethylfluorene, diphenylfluorene or spirobifluorene.

According to one embodiment of the present invention, each of R ₂ and R ₃ is an alkyl group having 1 to 6 carbon atoms.

According to one embodiment of the present specification, R ₂ and R ₃ are each an alkyl group having 1 to 5 carbon atoms.

According to one embodiment of the present disclosure, R ₂ and R ₃ are alkyl groups having 1 to 5 carbon atoms.

According to one embodiment of the present disclosure, R ₂ and R ₃ are each a methyl group.

According to one embodiment of the present disclosure, R ₁ is a phenyl group, and R ₂ and R ₃ are alkyl groups having 1 to 5 carbon atoms.

According to one embodiment of the present disclosure, R ₁ is a phenyl group, and R ₂ and R ₃ are methyl groups.

According to one embodiment of the present invention, R ₄ and R ₅ are the same or different and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a ring.

According to one embodiment of the present invention, R ₄ and R ₅ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; Or a substituted or unsubstituted phenyl group, or are bonded to each other to form a substituted or unsubstituted fluorene.

According to one embodiment of the present invention, R ₄ and R ₅ are the same or different and each independently is an alkyl group having 1 to 6 carbon atoms; Or a phenyl group, or combine with each other to form fluorene, dimethylfluorene, diphenylfluorene or spirobifluorene.

According to one embodiment of the present invention, each of R ₄ and R ₅ is an alkyl group having 1 to 6 carbon atoms.

According to one embodiment of the present disclosure, R ₄ and R ₅ are each a methyl group.

According to one embodiment of the present disclosure, R < ₁₁ > And R < ₁₂ > are the same or different from each other, and each independently hydrogen; heavy hydrogen; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. When an electron-withdrawing group such as a nitrile group or a halogen group is introduced into R ₁₁ or R ₁₂ , the electron density of the heterocycle connected to R ₁₁ or R ₁₂ is reduced to be lower than that of a substance substituted with an alkyl group, The HOMO energy level can be reduced. Therefore, the hole injecting ability may be lowered.

According to one embodiment of the present disclosure, R ₁₁ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R ₁₁ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group.

According to one embodiment of the present disclosure, R ₁₁ is selected from the group consisting of hydrogen; Or deuterium.

According to one embodiment of the present disclosure, R < ₁₁ > is hydrogen.

According to one embodiment of the present disclosure, R ₁₂ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R ₁₂ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group.

According to one embodiment of the present disclosure, R ₁₂ is selected from the group consisting of hydrogen; Or deuterium.

According to one embodiment of the present disclosure, R ₁₂ is hydrogen.

According to one embodiment of the present disclosure, R ₁₃ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R ₁₃ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group.

According to one embodiment of the present disclosure, R ₁₃ is selected from the group consisting of hydrogen; Or deuterium.

According to one embodiment of the present disclosure, R ₁₃ is hydrogen.

According to one embodiment of the present disclosure, R ₁₄ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R ₁₄ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group.

According to one embodiment of the present disclosure, R ₁₄ is selected from the group consisting of hydrogen; Or deuterium.

According to one embodiment of the present disclosure, R ₁₄ is hydrogen.

According to one embodiment of the present disclosure, R ₁₅ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, R ₁₅ is selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group.

According to one embodiment of the present disclosure, R ₁₅ is selected from the group consisting of hydrogen; Or deuterium.

According to one embodiment of the present disclosure, R ₁₅ is hydrogen.

According to one embodiment of the present disclosure, R ₁₃ to R ₁₅ are hydrogen.

According to one embodiment of the present disclosure, R ₁₁ to R ₁₅ are hydrogen.

According to one embodiment of the present disclosure, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

According to one embodiment of the present disclosure, Ar ₁ and Ar ₂ are phenyl groups.

According to one embodiment of the present disclosure, Ar < ₃ > is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

According to one embodiment of the present disclosure, Ar < ₃ > is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted cycloalkyl group.

According to one embodiment of the present disclosure, Ar ₃ is an aryl group.

According to one embodiment of the present disclosure, Ar ₃ is an aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present disclosure, Ar ₃ is an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present disclosure, Ar ₃ is a phenyl group; A biphenyl group; Or a terphenyl group.

According to one embodiment of the present invention, Ar ₃ is a substituted or unsubstituted phenyl group.

According to one embodiment of the present disclosure, Ar ₃ is a phenyl group.

According to one embodiment of the present disclosure, Ar < ₃ > is hydrogen; Or deuterium.

According to one embodiment of the present disclosure, Ar < ₃ > is hydrogen.

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

The compound represented by the above formula (1) can be produced based on the following production example. According to one embodiment, it can be prepared in the following manner.

[Reaction Scheme 1]

In the above Reaction Scheme 1, the definitions of substituents are as defined in Chemical Formula (1).

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 and transporting holes, and the hole injecting layer, the hole transporting layer, (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 an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound of the above formula (1).

In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound of the above formula (1).

In another embodiment, the organic material layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer includes the compound of the above formula (1).

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.

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 addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method 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 material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection 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 (Alq3); 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 include a host material and a dopant material. The host material is 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.

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 arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino 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 material 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. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq3; 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.

< Manufacturing example  1> P1 Manufacturing

(10.0 g, 40.6 mmol), 4- (cyanophenyl) boronic acid (6.0 g, 40.6 mmol) and potassium carbonate (17.0 g, 123 mmol) Was suspended in a mixture of water (50 mL) and hydrofuran (100 mL). After nitrogen charging, tetrakis (triphenylphosphine) palladium (0.9 g, 0.7 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 12 hours. After cooling to room temperature, the resulting solid was filtered. The pale brown solid was precipitated in ethyl acetate, stirred and filtered to give white solid P1 (9.5 g, 88%).

Compounds P2 to P24 were prepared as shown in the following Table 1 according to the production method of Compound P1 of Production Example 1.

Intermediate 1 Intermediate 2 Compound (Px) Yield
(%) MS
[M + H] &lt; Manufacturing example
2
(P2)

87 269 Manufacturing example
3
(P3)

77 385 Manufacturing example
4
(P4)

75 375 Manufacturing example
5
(P5)

48 444 Manufacturing example
6
(P6)

65 384 Manufacturing example
7
(P7)

88 269 Manufacturing example
8
(P8)

85 269 Manufacturing example
9
(P9)

73 385 Manufacturing example
10
(P10)

75 375 Manufacturing example
11
(P11)

46 444 Manufacturing example
12
(P12)

64 384 Manufacturing example
13
(P13)

83 269 Manufacturing example
14
(P14)

82 269 Manufacturing example
15
(P15)

73 385 Manufacturing example
16
(P16)

70 375 Manufacturing example
17
(P17)

43 444 Manufacturing example
18
(P18)

70 384 Manufacturing example
19
(P19)

82 269 Manufacturing example
20
(P20)

73 269 Manufacturing example
21
(P21)

78 385 Manufacturing example
22
(P22)

85 375 Manufacturing example
23
(P23)

47 444 Manufacturing example
24
(P24)

80 384

< Manufacturing example  25> P25 Manufacturing

9-phenyl-9H-carbazole (10.0 g, 31 mmol), (4-chlorophenyl) boronic acid (5.4 g, 34 mmol) and potassium carbonate g, 93 mmol) was suspended in a mixture of tetrahydrofuran (100 mL) and water (30 mL). After nitrogen charging, tetrakis (triphenylphosphine) palladium (0.35 g, 0.3 mmol) was added to the suspension. Under nitrogen, the mixture was stirred at reflux for about 12 hours. After cooling to room temperature, the reaction was diluted with ethyl acetate and washed twice with water. The organic layer was separated, treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Ethanol was added in an excess amount while remaining a small amount of ethyl acetate, stirred at room temperature for 30 minutes, and the resulting solid was filtered. Compound P25 (9.0 g, 82%) was obtained as a pale brown solid.

Compounds P26 to P32 were prepared as shown in the following Table 2 according to the production method of the compound P25 in Production Example 25.

Intermediate 1 Intermediate 2 Compound (Px) Yield
(%) MS
[M + H] &lt; Manufacturing example
26
(P26)

80 354 Manufacturing example
27
(P27)

62 354 Manufacturing example
28
(P28)

64 354 Manufacturing example
29
(P29)

75 354 Manufacturing example
30
(P30)

80 354 Manufacturing example
31
(P31)

75 354 Manufacturing example
32
(P32)

73 354 Manufacturing example
33
(P33)

75 305 Manufacturing example
34
(P34)

75 305

< Manufacturing example  Preparation of Formula 1-1

(11.6 g, 33 mmol) and bis (tritiated-butylphosphine) palladium (0.15 g, 0.3 mmol) were added to a solution of the compound P1 (8.2 g, 30.5 mmol) mmol) and sodium tertiary-butoxide (5.8 g, 61 mmol) were mixed and refluxed in xylene (100 ml) under nitrogen for 6 hours with stirring. After the temperature is lowered to room temperature, the resulting solid is filtered, and the obtained solid is dissolved in chloroform, washed with water, and the organic layer is separated, treated with anhydrous magnesium sulfate and filtered. Ethyl acetate was added to the compound in the form of a solution and recrystallized to obtain a white solid compound (1-1) (12 g, 72%).

Compounds represented by Formulas 1-2 to 1-96 were prepared according to the production method of Formula 1-1 of Preparation Example 35, and the structures, yields and MS data of the compounds shown in Table 3 were summarized.

Intermediate 1
(Px) Intermediate 2
(Px) The Yield
(%) MS
[M + H] &lt; Manufacturing example
36
The
1-2 P1 P26

75 586 Manufacturing example
37
The
1-3 P1 P27

63 586 Manufacturing example
38
The
1-4 P1 P28

60 586 Manufacturing example
39
The
1-5 P1 P29

75 586 Manufacturing example
40
The
1-6 P1 P30

74 586 Manufacturing example
41
The
1-7 P1 P31

73 586 Manufacturing example
42
The
1-8 P1 P32

68 586 Manufacturing example
43
The
1-9 P1 P34

70 537 Manufacturing example
44
The
1-10 P2 25

80 586 Manufacturing example
45
The
1-11 P2 P26

82 586 Manufacturing example
46
The
1-12 P2 P27

59 586 Manufacturing example
47
The
1-13 P2 P28

62 586 Manufacturing example
48
The
1-14 P2 P29

75 586 Manufacturing example
49
The
1-15 P2 P30

76 586 Manufacturing example
50
The
1-16 P2 P31

65 586 Manufacturing example
51
The
1-17 P2 P32

68 586 Manufacturing example
52
The
1-18 P2 P34

72 537 Manufacturing example
53
The
1-19 P3 25

75 702 Manufacturing example
54
The
1-20 P3 P26

79 702 Manufacturing example
55
The
1-21 P3 P27

58 702 Manufacturing example
56
The
1-22 P3 P28

60 702 Manufacturing example
57
The
1-23 P3 P29

64 702 Manufacturing example
58
The
1-24 P3 P30

65 702 Manufacturing example
59
The
1-25 P3 P31

68 702 Manufacturing example
60
The
1-26 P3 P32

65 702 Manufacturing example
61
The
1-27 P3 P34

69 653 Manufacturing example
62
The
1-28 P4 25

70 692 Manufacturing example
63
The
1-29 P4 P26

74 692 Manufacturing example
64
The
1-30 P4 P27

63 692 Manufacturing example
65
The
1-31 P4 P28

62 692 Manufacturing example
66
The
1-32 P4 P29

70 692 Manufacturing example
67
The
1-33 P4 P30

72 692 Manufacturing example
68
The
1-34 P4 P31

68 692 Manufacturing example
69
The
1-35 P4 P32

72 692 Manufacturing example
70
The
1-36 P4 P34

69 643 Manufacturing example
71
The
1-37 P5 25

68 761 Manufacturing example
72
The
1-38 P5 P26

67 761 Manufacturing example
73
The
1-39 P5 P27

59 761 Manufacturing example
74
The
1-40 P5 P28

55 761 Manufacturing example
75
The
1-41 P5 P29

68 761 Manufacturing example
76
The
1-42 P5 P30

70 761 Manufacturing example
77
The
1-43 P5 P31

65 761 Manufacturing example
78
The
1-44 P5 P34

64 761 Manufacturing example
79
The
1-45 P5 P34

65 712 Manufacturing example
80
The
1-46 P6 25

69 701 Manufacturing example
81
The
1-47 P6 P26

72 701 Manufacturing example
82
The
1-48 P6 P27

63 701 Manufacturing example
83
The
1-49 P6 P28

64 701 Manufacturing example
84
The
1-50 P6 P29

72 701 Manufacturing example
85
The
1-51 P6 P30

75 701 Manufacturing example
86
The
1-52 P6 P31

71 701 Manufacturing example
87
The
1-53 P6 P32

72 701 Manufacturing example
88
The
1-54 P6 P34

70 652 Manufacturing example
89
The
1-55 P7 P25

75 586 Manufacturing example
90
The
1-56 P7 P26

75 586 Manufacturing example
91
The
1-57 P7 P27

52 586 Manufacturing example
92
The
1-58 P7 P28

48 586 Manufacturing example
93
The
1-59 P7 P29

70 586 Manufacturing example
94
The
1-60 P7 P30

74 586 Manufacturing example
95
The
1-61 P7 P31

72 586 Manufacturing example
96
The
1-62 P7 P32

68 586 Manufacturing example
97
The
1-63 P7 P34

70 537 Manufacturing example
98
The
1-64 P8 P25

72 586 Manufacturing example
99
The
1-65 P8 P26

80 586 Manufacturing example
100
The
1-66 P8 P27

67 586 Manufacturing example
101
The
1-67 P8 P28

59 586 Manufacturing example
102
The
1-68 P8 P29

72 586 Manufacturing example
103
The
1-69 P8 P30

75 586 Manufacturing example
104
The
1-70 P8 P31

71 586 Manufacturing example
105
The
1-71 P8 P32

68 586 Manufacturing example
106
The
1-72 P8 P34

70 537 Manufacturing example
107
The
1-73 P9 P25

65 702 Manufacturing example
108
The
1-74 P9 P26

70 702 Manufacturing example
109
The
1-75 P9 P27

57 702 Manufacturing example
110
The
1-76 P9 P28

60 702 Manufacturing example
111
The
1-77 P9 P29

64 702 Manufacturing example
112
The
1-78 P9 P30

70 702 Manufacturing example
113
The
1-79 P9 P31

68 702 Manufacturing example
114
The
1-80 P9 P32

65 702 Manufacturing example
115
The
1-81 P10 P25

70 692 Manufacturing example
116
The
1-82 P10 P26

74 692 Manufacturing example
117
The
1-83 P10 P27

63 692 Manufacturing example
118
The
1-84 P10 P28

62 692 Manufacturing example
119
The
1-85 P10 P29

70 692 Manufacturing example
120
The
1-86 P10 P30

70 692 Manufacturing example
121
The
1-87 P10 P31

74 692 Manufacturing example
122
The
1-88 P10 P32

65 692 Manufacturing example
123
The
1-89 P10 P34

67 643 Manufacturing example
124
The
1-90 P11 P25

75 761 Manufacturing example
125
The
1-91 P11 P26

76 761 Manufacturing example
126
The
1-92 P11 P27

55 761 Manufacturing example
127
The
1-93 P11 P28

56 761 Manufacturing example
128
The
1-94 P11 P29

70 761 Manufacturing example
129
The
1-95 P11 P30

74 761 Manufacturing example
130
The
1-96 P11 P31

68 761 Manufacturing example
131
The
1-97 P11 P32

68 761 Manufacturing example
132
The
1-98 P11 P34

70 712 Manufacturing example
133
The
1-99 P12 P25

72 701 Manufacturing example
134
The
1-100 P12 P26

73 701 Manufacturing example
135
The
1-101 P12 P27

56 701 Manufacturing example
136
The
1-102 P12 P28

59 701 Manufacturing example
137
The
1-103 P12 P29

72 701 Manufacturing example
138
The
1-104 P12 P30

72 701 Manufacturing example
139
The
1-105 P12 P31

68 701 Manufacturing example
140
The
1-106 P12 P32

64 701 Manufacturing example
141
The
1-107 P12 P34

65 652

< Experimental Example  1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1500 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.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the ITO transparent electrode thus prepared to a thickness of 500 Å to form a hole injection layer.

[LINE]

An NPB (N, N-Bis- (1-naphthalenyl) -N, N-bis-phenyl- (1,1- biphenyl) -4,4- diamine) compound having the following structure was deposited on the hole injection layer to a thickness of 400 Å To form a hole transporting layer.

[NPB]

Subsequently, the compound of Formula 1-1 prepared in Preparation Example 35 was vacuum deposited on the hole transport layer to a film thickness of 300 Å at a concentration of 10% (weight ratio Wt%) with Ir (ppy) 3 dopant to form a light emitting layer.

The following electron transport material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer.

[Electron transport material]

Lithium fluoride (LiF) and aluminum having a thickness of 2000 Å were sequentially deposited on the electron injection and transport layer to a thickness of 12 Å to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr.

<Experimental Example 2>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-73 was used in place of the compound of Formula 1-1.

<Experimental Example 3>

In the same manner as in Experimental Example 1, except that the compound of Formula 1-90 was used in place of the compound of Formula 1-1.

&Lt; Comparative Example 1 &

In the same manner as in Experimental Example 1, except that H1 was used instead of the compound of Formula 1-1.

&Lt; Comparative Example 2 &

In the same manner as in Experimental Example 1, except that the above-mentioned H2 was used in place of the compound of Formula 1-1.

The results of the devices fabricated by using the respective compounds in Experimental Examples 1 to 3 as the light emitting layer are shown in the following table.

In the above Experimental Example, when a material having no substituent of - (L) _s -Y is used as a light emitting layer as in Comparative Example 2, the electron injection characteristic into the light emitting layer deteriorates and the efficiency of the device deteriorates.

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

Claims (15)

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

In Formula 1,
X is _{NR 1, CR 2 R 3,} SiR 4 R 5, S or O,
L are the same or different and are each independently a direct bond; Substituted or unsubstituted arylene; Or substituted or unsubstituted heteroarylene,
Y is CN, P (= O) Ar 1 Ar 2, or SO ₂ Ar _3,
Ar ₁ and Ar ₂ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Ar ₃ is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; Or a substituted or unsubstituted aryl group,
R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or is bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,
R ₁₃ , R ₁₄ and R ₁₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring or a heterocyclic ring,
R ₁₁ And R &lt; ₁₂ &gt; are the same or different from each other, and each independently hydrogen; heavy hydrogen; An amino group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
n, p and q are the same or different and each is an integer of 1 to 4,
m, r and s are the same or different and each is an integer of 1 to 3,
when n is 2 or more, R &lt; ₁₁ &gt; are the same or different from each other,
When m is 2 or more, R ₁₂ are the same or different from each other,
when p is 2 or more, R ₁₃ are the same or different from each other, q
Lt; ₁₄ &gt; are the same or different from each other,
When r is 2 or more, R &lt; ₁₅ &gt;
When s is 2 or more, L is the same or different from each other. The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 2 to 6:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above Formulas 2 to 6,
The definitions of Y, L, R ₁ to R ₅ , R ₁₁ to R ₁₅ , n, m, p, q, r and s are as shown in formula (1). The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas (7) to (9):
(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas (7) to (9)
The definitions of Y, L, R ₁ to R ₅ , R ₁₁ to R ₁₅ , n, m, p, q, r and s are as shown in formula (1). The heterocyclic compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 10:
[Chemical formula 10]

In Formula 10,
Y, R ₁ to R ₅ , R ₁₁ to R ₁₅ , n, m, p, q and r are as defined in formula (1).
According to one embodiment of the present invention, the formula (1) may be represented by the following formula (10). The heterocyclic compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 11:
(11)

In Formula 11,
Y, R ₁ to R ₅ , R ₁₁ to R ₁₅ , n, m, p, q and r are as defined in formula (1). 2. The compound according to claim 1, wherein L is phenylene; Fluorenylene substituted with an alkyl group; Or dibenzothiophene. The compound according to claim 1, wherein R ₁ is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, R ₂ and R ₃ are the same or different and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a ring; R ₄ and R ₅ are the same or different and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or is bonded to each other to form a ring. The heterocyclic compound according to claim 1, wherein R ₁ is a phenyl group, and R ₂ and R ₃ are an alkyl group having 1 to 5 carbon atoms. The heterocyclic compound according to claim 1, wherein R11 to R15 are hydrogen. 2. The heterocyclic compound according to claim 1, wherein Ar1 to Ar3 are phenyl groups. The heterocyclic compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:

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 heterocyclic compound according to any one of claims 1 to 11 Lt; / RTI &gt; [12] The organic EL device according to claim 12, wherein the organic compound layer including the heterocyclic compound comprises a hole injection layer; A hole transport layer; Or a layer which simultaneously injects holes and transports holes. 14. The organic electroluminescent device according to claim 12, wherein the organic compound layer comprising the compound comprises an electron injecting layer; An electron transport layer; Or an electron injection and electron transporting layer simultaneously. 14. The organic light emitting device according to claim 12, wherein the organic compound layer containing the compound is a light emitting layer.

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