KR20220009674A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light emitting device including the same. A compound of the present invention can be used as a material for an organic layer of the organic light emitting device. When the organic light emitting device is manufactured by including the compound of the present invention, the organic light emitting device having high efficiency, low voltage, and long lifespan characteristics can be obtained.

Description

Heterocyclic compound and organic light-emitting device comprising the same

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

In the present specification, an organic light emitting device is a light emitting device using an organic semiconductor material, and requires the exchange of holes and/or electrons between the electrode and the organic semiconductor material. The organic light emitting diode can be roughly divided into two types as follows according to the principle of operation. First, excitons are formed in the organic material layer by photons flowing into the device from an external light source, the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as a current source (voltage source) It is a type of light emitting device that becomes The second is a light emitting device of a type that applies a voltage or current to two or more electrodes to inject holes and/or electrons into an organic semiconductor material layer forming an interface with the electrodes, and operates by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, etc. can get In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

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

In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The principle is that when a small amount of a dopant having a smaller energy band gap and superior luminous efficiency than the host constituting the emission layer is mixed in a small amount in the emission layer, excitons generated from the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

In order to sufficiently exhibit the excellent characteristics of the above-described organic light emitting device, materials constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron suppressing material, an electron transport material, an electron injection material, etc. are stable and efficient materials. The development of new materials continues to be demanded as it is supported by

International Patent Publication No. 2017-126443

In the present specification, a heterocyclic compound and an organic light emitting device including the same are described.

An exemplary embodiment of the present specification provides a heterocyclic compound of Formula 1 below.

[Formula 1]

In Formula 1,

X is O or S;

At least one of A1 to A16 is represented by the following formula (2), and the remainder is hydrogen,

[Formula 2]

In Formula 2,

The dotted line is a portion connected to at least one of A1 to A16 of Formula 1,

one of B1 or B2 is -CCN, the other is N,

R1 and R2 are the same as or different from each other, and each independently represents an aryl group unsubstituted or substituted with deuterium, CN, an alkyl group, a haloalkyl group, a haloalkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ; a silyl group unsubstituted or substituted with deuterium, CN, an alkyl group, or an aryl group; Or a heterocyclic group unsubstituted or substituted with deuterium, CN, an alkyl group, or a substituted or unsubstituted aryl group,

L is a direct bond; an arylene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; Or an alkyl group, an aryl group, a heterocyclic group, and a divalent heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group substituted with an alkyl group,

n is an integer from 1 to 3,

When n is 2 or more, L of 2 or more are the same as or different from each other.

In addition, according to an exemplary embodiment of the present invention, the first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one organic material layer of the organic material layer provides an organic light-emitting device including the above-described heterocyclic compound.

The compound of the present invention may be used as a material for an organic layer of an organic light emitting device. When an organic light emitting device is manufactured by including the compound of the present invention, an organic light emitting device having high efficiency, low voltage and long lifespan characteristics can be obtained. It is possible to lower the driving voltage and improve the light efficiency.

1 and 2 show an example of an organic light emitting device according to the present invention.

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

The present specification provides a heterocyclic compound represented by the following formula (1). When the heterocyclic compound represented by the following Chemical Formula 1 is used in the organic material layer of the organic light emitting device, the efficiency and lifespan characteristics of the organic light emitting device are improved. In particular, the conventional compound having a high sublimation temperature has a low compound stability, and when applied to a device, the efficiency and lifespan of the device are deteriorated. , it has a low sublimation temperature and high stability, so that when applied to a device, a device having excellent efficiency and long life can be obtained.

In addition, the heterocyclic compound represented by the following Chemical Formula 1 includes a cycloalkene ring in the molecule, thereby increasing solubility and thus can be applied for a solution process.

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

In this specification, when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group (-CN); silyl group; boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more 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.

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

In the present 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 -SiY1Y2Y3, wherein Y1, Y2 and Y3 are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. 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, a phenylsilyl group, and the like, but is not limited thereto. does not

In the present specification, the boron group may be represented by the formula of -BY4Y5, wherein Y4 and Y5 are each hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. Specifically, the boron group includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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

In the present specification, the amine group is -NH ₂ ; an alkylamine group; N-alkylarylamine group; arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; dimethylamine group; ethylamine group; diethylamine group; phenylamine group; naphthylamine group; biphenylamine group; anthracenylamine group; 9-methylanthracenylamine group; diphenylamine group; N-phenylnaphthylamine group; ditolylamine group; N-phenyltolylamine group; triphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group and the like, but is not limited thereto.

In the present specification, the N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the above-described alkyl group. Specifically, the alkyl thiooxy group includes a methyl thiooxy group; ethyl thiooxy group; tert-butyl thiooxy group; hexyl thiooxy group; octylthiooxy group and the like, and examples of the alkylsulfoxy group include mesyl; ethyl sulfoxy group; propyl sulfoxy group; Butyl sulfoxy group and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is 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 an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may include, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like.

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, and the like. However, the present invention is not limited thereto.

In the present specification, the arylene group is the same as defined for the aryl group, except that it is a divalent group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-8 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8, B1, B2, R1, R2, X, L, and n are as defined in Formula 2 above.

According to an exemplary embodiment of the present specification, X is O.

According to an exemplary embodiment of the present specification, X is S.

According to an exemplary embodiment of the present specification, among A1 to A16, A1 is Chemical Formula 2, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, A2 of A1 to A16 is Chemical Formula 2, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, A3 of A1 to A16 is Chemical Formula 2, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, among A1 to A16, A4 is Chemical Formula 2, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, A5 of A1 to A16 is Chemical Formula 2, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, among A1 to A16, A6 is Chemical Formula 2, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, among A1 to A16, A7 is Chemical Formula 2, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, A8 of A1 to A16 is Chemical Formula 2, and the remainder is hydrogen.

According to an exemplary embodiment of the present specification, in A1 to A16, any one of A1, A2, and A3 is Chemical Formula 2, and the rest is hydrogen.

According to an exemplary embodiment of the present specification, in A1 to A16, any one of A6, A7, and A8 is Chemical Formula 2, and the rest is hydrogen.

According to an exemplary embodiment of the present specification, B1 is -CCN, and B2 is N.

According to an exemplary embodiment of the present specification, B2 is -CCN, and B1 is N.

According to an exemplary embodiment of the present specification, the L is a direct bond; an arylene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; or a divalent heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group, an aryl group, a heterocyclic group, and an aryl group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, the L is a direct bond; or an arylene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group.

According to an exemplary embodiment of the present specification, the L is a direct bond; arylene group; or a divalent heterocyclic group.

According to an exemplary embodiment of the present specification, the L is a direct bond; an unsubstituted arylene group; or an unsubstituted divalent heterocyclic group.

According to an exemplary embodiment of the present specification, the L is a direct bond; It is an unsubstituted arylene group.

According to an exemplary embodiment of the present specification, the L is a direct bond; phenylene group; biphenylene group; anthracenylene group; phenanthrenylene group; or a naphthylene group.

According to an exemplary embodiment of the present specification, the L is a direct bond, a phenylene group, or a naphthylene group.

According to an exemplary embodiment of the present specification, the L is a direct bond or a phenylene group.

According to an exemplary embodiment of the present specification, the L is a direct bond.

According to an exemplary embodiment of the present specification, the L is a phenylene group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently an aryl group unsubstituted or substituted with deuterium, CN, an alkyl group, an aryl group, or a heteroaryl group; Or a heterocyclic group unsubstituted or substituted with deuterium, CN, an alkyl group, or an aryl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently an aryl group unsubstituted or substituted with deuterium, CN, an alkyl group, an aryl group, or a heteroaryl group; Or a heterocyclic group unsubstituted or substituted with CN or an aryl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently an aryl group or a heteroaryl group, and the aryl group or heteroaryl group is deuterium, CN, an alkyl group, a substituted or unsubstituted aryl group. , and may be substituted or unsubstituted with any one or more substituents selected from a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently represent an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 3 to 30 carbon atoms, and the aryl group having 6 to 30 carbon atoms or carbon number The heteroaryl group of 3 to 30 may be substituted or unsubstituted with any one or more substituents selected from deuterium, CN, an alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and the aryl group having 6 to 20 carbon atoms or carbon number The 3 to 20 heteroaryl group is any one selected from deuterium, CN, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms It may be substituted or unsubstituted with one or more substituents.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrene group , a phenalene group, a triazine group, a pyrimidine group, a pyridine group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, terphenyl group, fluorene group, phenanthrene group, anthracene group, triphenylene group, pyrene group, phenalene group, triazine group, pyrimidine group, pyridine group, carbazole group, dibenzofuran group , or the dibenzothiophene group is any one selected from deuterium, CN, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms It may be substituted or unsubstituted with one or more substituents.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, a phenanthrene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, terphenyl group, fluorene group, phenanthrene group, carbazole group, dibenzofuran group, or dibenzothiophene group is deuterium, CN, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted It may be substituted or unsubstituted with any one or more substituents selected from an aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, a phenanthrene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, terphenyl group, fluorene group, phenanthrene group, carbazole group, dibenzofuran group, or dibenzothiophene group is deuterium; CN; methyl group; ethyl group; isopropyl group; terbutyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; And it may be substituted or unsubstituted with any one or more substituents selected from a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, a phenanthrene group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group,

The phenyl group, biphenyl group, naphthyl group, fluorene group or carbazole group is deuterium; CN; methyl group; ethyl group; isopropyl group; terbutyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted phenanthrene group; And it may be substituted or unsubstituted with any one or more substituents selected from a substituted or unsubstituted carbazole group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently a dibenzofuran group; dibenzothiophene group; CN-substituted or unsubstituted carbazole group; terphenyl group; phenanthrene group; a fluorene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or CN; a naphthyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with CN or an aryl group having 6 to 20 carbon atoms; a phenyl group unsubstituted or substituted with deuterium, a naphthyl group, CN, or a phenanthrene group; a phenyl group substituted with carbazole; a phenyl group substituted with carbazole substituted with CN; a phenyl group substituted with a fluorene group substituted with a methyl group; or a phenyl group substituted with a dimethylfluorene group substituted with CN and a methyl group.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and independently a dibenzofuran group; dibenzothiophene group; CN-substituted or unsubstituted carbazole group; terphenyl group; phenanthrene group; a fluorene group unsubstituted or substituted with a methyl group or CN; a naphthyl group unsubstituted or substituted with a phenyl group; CN-substituted or unsubstituted biphenyl group; a phenyl group unsubstituted or substituted with deuterium, a naphthyl group, CN, or a phenanthrene group; a phenyl group substituted with carbazole; a phenyl group substituted with carbazole substituted with CN; a phenyl group substituted with a dimethyl fluorene group; or a phenyl group substituted with a dimethylfluorene group substituted with CN.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as each other.

According to an exemplary embodiment of the present specification, R1 and R2 are the same as each other and are a phenyl group, a biphenyl group, or a naphthyl group.

According to an exemplary embodiment of the present specification, R1 and R2 are different from each other.

According to an exemplary embodiment of the present specification, R1 and R2 are different from each other, and each independently a dibenzofuran group; dibenzothiophene group; CN-substituted or unsubstituted carbazole group; terphenyl group; phenanthrene group; A fluorene group unsubstituted or substituted with an alkyl group or CN; a naphthyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with CN or an aryl group; a phenyl group unsubstituted or substituted with deuterium, a naphthyl group, CN, or a phenanthrene group; a phenyl group unsubstituted or substituted with carbazole; a phenyl group unsubstituted or substituted with carbazole substituted with CN; a phenyl group unsubstituted or substituted with a dimethyl fluorene group; Or a phenyl group unsubstituted or substituted with a dimethylfluorene group substituted with CN.

According to an exemplary embodiment of the present specification, R1 is an aryl group unsubstituted or substituted with deuterium, CN, an alkyl group, an aryl group, or a heteroaryl group; Or a heterocyclic group unsubstituted or substituted with CN or an aryl group.

According to an exemplary embodiment of the present specification, R2 is an aryl group unsubstituted or substituted with deuterium, CN, an alkyl group, an aryl group, or a heteroaryl group; Or a heterocyclic group unsubstituted or substituted with CN or an aryl group.

According to an exemplary embodiment of the present specification, R1 is an aryl group having 6 to 30 carbon atoms, and the aryl group having 6 to 30 carbon atoms is deuterium, CN, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted hetero It is unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, R1 is a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, or a phenanthrene group, and the phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, or a phenanthrene group the group is deuterium; CN; an alkyl group having 1 to 5 carbon atoms; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; And it may be substituted or unsubstituted with any one or more substituents selected from a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, R1 is a terphenyl group; phenanthrene group; A fluorene group unsubstituted or substituted with an alkyl group or CN; a naphthyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with CN or an aryl group; a phenyl group unsubstituted or substituted with deuterium, a naphthyl group, CN, or a phenanthrene group; a phenyl group unsubstituted or substituted with carbazole; a phenyl group unsubstituted or substituted with carbazole substituted with CN; a phenyl group unsubstituted or substituted with a dimethyl fluorene group; Or a phenyl group unsubstituted or substituted with a dimethylfluorene group substituted with CN.

According to an exemplary embodiment of the present specification, R1 is a heterocyclic group unsubstituted or substituted with CN or an aryl group.

According to an exemplary embodiment of the present specification, R1 is a heterocyclic group containing 3 to 20 carbon atoms, N, O, or S unsubstituted or substituted with CN or an aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is a triazine group, a pyrimidine group, a pyridine group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group, and the triazine group, pyrimidine group, pyridine group, carba The sol group, dibenzofuran group, or dibenzothiophene group is unsubstituted or substituted with CN or an aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is a carbazole group, a dibenzofuran group, or a dibenzothiophene group, and the carbazole group, dibenzofuran group, or dibenzothiophene group is CN or having 6 to 20 carbon atoms. It is unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, R1 is a carbazole group, a dibenzofuran group, or a dibenzothiophene group, and the carbazole group, a dibenzofuran group, or a dibenzothiophene group is CN; an alkyl group having 1 to 5 carbon atoms; phenyl group; biphenyl group; naphthyl group; fluorene group; And it may be unsubstituted or substituted with any one or more substituents selected from a phenanthrene group.

According to an exemplary embodiment of the present specification, R1 is a carbazole group, a dibenzofuran group, or a dibenzothiophene group, and the carbazole group may be unsubstituted or substituted with CN.

According to an exemplary embodiment of the present specification, R2 is an aryl group having 6 to 30 carbon atoms, and the aryl group having 6 to 30 carbon atoms is deuterium, CN, an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted hetero It is unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, R2 is a phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, or a phenanthrene group, and the phenyl group, a biphenyl group, a naphthyl group, a terphenyl group, a fluorene group, or a phenanthrene group the group is deuterium; CN; an alkyl group having 1 to 5 carbon atoms; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; And it may be substituted or unsubstituted with any one or more substituents selected from a substituted or unsubstituted dibenzothiophene group.

According to an exemplary embodiment of the present specification, R2 is a terphenyl group; phenanthrene group; A fluorene group unsubstituted or substituted with an alkyl group or CN; a naphthyl group unsubstituted or substituted with an aryl group; a biphenyl group unsubstituted or substituted with CN or an aryl group; a phenyl group unsubstituted or substituted with deuterium, a naphthyl group, CN, or a phenanthrene group; a phenyl group unsubstituted or substituted with carbazole; a phenyl group unsubstituted or substituted with carbazole substituted with CN; a phenyl group unsubstituted or substituted with a dimethyl fluorene group; Or a phenyl group unsubstituted or substituted with a dimethylfluorene group substituted with CN.

According to an exemplary embodiment of the present specification, R2 is a heterocyclic group unsubstituted or substituted with CN or an aryl group.

According to an exemplary embodiment of the present specification, R2 is CN or a heterocyclic group including N, O, or S having 3 to 20 carbon atoms, which is unsubstituted or substituted with CN or an aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R2 is a triazine group, a pyrimidine group, a pyridine group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group, and the triazine group, pyrimidine group, pyridine group, carba The sol group, dibenzofuran group, or dibenzothiophene group is unsubstituted or substituted with CN or an aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R2 is a carbazole group, dibenzofuran group, or dibenzothiophene group, and the carbazole group, dibenzofuran group, or dibenzothiophene group is CN or having 6 to 20 carbon atoms. It is unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, R2 is a carbazole group, a dibenzofuran group, or a dibenzothiophene group, and the carbazole group, a dibenzofuran group, or a dibenzothiophene group is CN; an alkyl group having 1 to 5 carbon atoms; phenyl group; biphenyl group; naphthyl group; fluorene group; And it may be unsubstituted or substituted with any one or more substituents selected from a phenanthrene group.

According to an exemplary embodiment of the present specification, R2 is a carbazole group, a dibenzofuran group, or a dibenzothiophene group, and the carbazole group may be unsubstituted or substituted with CN.

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following structures.

Substituents of the compound of Formula 1 may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.

The conjugation length of the compound and the energy bandgap 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 band gaps can be synthesized by introducing various substituents into the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the structure as described above.

In addition, by introducing various substituents into the core structure of the structure as described above, a compound having the intrinsic properties of the introduced substituent can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, a material satisfying the conditions required for each organic material layer can be synthesized. can

In addition, the organic light emitting device according to the present invention includes a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.

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

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing 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 multi-layer 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 injection layer, a hole transport layer, a layer that simultaneously injects and transports holes, a light emitting layer, an electron transport layer, an electron injection layer, etc. 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 material layers or a larger number of organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers is represented by Formula 1 Heterocyclic compounds may be included.

In another organic light emitting device, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a heterocyclic compound represented by Formula 1 above.

In the organic light emitting device of the present invention, the organic material layer may include at least one of a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes, and at least one of the layers is represented by Formula 1 Heterocyclic compounds may be included.

In another organic light emitting device, the organic material layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a heterocyclic compound represented by Formula 1 above.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes a heterocyclic compound represented by Formula 1 above. As an example, the heterocyclic compound represented by Formula 1 may be included as a dopant in the emission layer.

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

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

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

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

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

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

(5) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

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

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

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

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

(10) anode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / cathode

(11) anode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / electron injection layer / cathode

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

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

(14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(18) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron injection and transport layer / cathode

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

1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1 . In such a structure, the heterocyclic compound represented by Formula 1 may be included in the light emitting layer 3 .

2 shows an anode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, a light emitting layer 8, an electron injection layer and an electron transport layer 9 on the substrate 1 And the structure of the organic light emitting device in which the cathode 4 is sequentially stacked is exemplified. The compound of the present specification is preferably included in the electron injection layer and the electron transport layer 9, but is not limited thereto.

For example, the organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide or an alloy thereof on a substrate. From the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that performs both electron transport and electron injection thereon After forming an organic material layer including one or more selected layers, it may be manufactured by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may have a multilayer 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. In addition, the organic layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a vapor deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

The anode is an electrode for injecting holes, and as the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and the cathode 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; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer. As the hole injection material, holes can be well injected from the anode at a low voltage, and the highest occupied (HOMO) of the hole injection material is The molecular orbital) is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto. The hole injection layer may have a thickness of 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, there is an advantage in that the hole injection characteristics can be prevented from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement There are advantages to avoiding this.

The hole transport layer may serve to facilitate hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

In one embodiment of the present invention, the organic light emitting device may include one or more hole transport layers, for example, may include a multi-layered hole transport layer such as a first hole transport layer and a second hole transport layer, each layer has an arylamine An organic material of the series, an organic material of the hexanitrile hexaazatriphenylene series may be used.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron-blocking layer may be the aforementioned spiro compound or a material known in the art.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

Examples of the host material for the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopant is PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium) ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a _{fluorescent material such as Alq 3} (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto. When the emission layer emits green light, a _{phosphor such as Ir(ppy) 3} (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, the present invention is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant includes a _{phosphorescent material such as (4,6-F2ppy) 2} Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), A fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

A condensed aromatic ring derivative substituted with an amine may be used as a dopant material for the light emitting layer. Specifically, a pyrene-based compound substituted with an amine may be used, and the host and the dopant are used in a weight ratio of 99:1 to 10:1.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

The electron transport layer may serve to facilitate the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transport properties can be prevented from being deteriorated, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from being raised to improve the movement of electrons. There are advantages that can be

The electron injection layer may serve to facilitate electron injection. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and , a compound having excellent thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

A layer that simultaneously injects and transports electrons separately from the electron transport layer and the electron injection layer may be used. The electron injection and transport layer may be configured in addition to the electron transport layer and the electron injection layer, or instead of the electron transport layer or the electron injection layer. For example, the organic light emitting diode may include an electron injection layer, an electron transport layer, all of the electron injection and transport layers, only one layer, or any two layers.

The electron injection or electron transport layer materials may be used together with a metal complex compound. As the metal binder, an alkali metal complex or an alkaline earth metal complex may be used. For example, a lithium metal complex may be used as the metal complex, and the ligand of Formula A-1 below may be used as the lithium metal complex.

[Formula A-1]

In the formula A-1,

Met is an alkali metal or alkaline earth metal,

Y1 is a methyl group, a phenyl group, a fluoro substituent, a condensed benzene ring group formed by combining two substituents,

y1 is an integer from 0 to 6, and when y1 is 2 or more, Y1 is the same as or different from each other,

met and y2 are integers from 1 to 6.

In an exemplary embodiment of the present invention, the electron injection or electron transport layer material is used together with lithium quinolate (Liq) in a mass ratio of 1:1.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

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

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

A method of preparing the compound of Formula 1 and manufacturing an organic light emitting device using the same will be described in detail in Examples below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

In the following reaction scheme, various types of intermediates can be synthesized by those skilled in the art by appropriately selecting known starting materials for the type and number of substituents. As the reaction type and reaction conditions, those known in the art may be used.

By appropriately combining the preparation formulas described in the Examples of the present specification and the intermediates based on common technical knowledge, all of the compounds of Formula 1 described in the present specification can be prepared.

< production example >

The heterocyclic compound represented by Chemical Formula 1 was prepared by introducing various kinds of nitrogen-containing heterogroups to spiroxanthin or spirothioxanthine substituted with boronic acid as follows.

production example 1-1. Synthesis of compound 1

Spiro [fluorene-9,9'-xanthine] -3'-ylboronic acid 15 g (39.9 mmol), 4-chloro-2,6-diphenylpyrimidine-5-carbonitrile 39.9 mmol, tetrahydro 150 mL of furan and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.9 g of Compound 1 (yield 89%).

MS[M+H]+ = 588

production example 1-2. Synthesis of compound 2

Spiro [fluorene-9,9'-xanthine] -3'-ylboronic acid 15 g (39.9 mmol), 4-chloro-6- (4- (naphthalen-2-yl) phenyl) -2-phenyl 39.9 mmol of pyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 21.9 g of compound 2 (yield 77%).

MS[M+H]+ = 714

production example 1-3. Synthesis of compound 3

Spiro [fluorene-9,9'-xanthine] -3'-ylboronic acid 15 g (39.9 mmol), 4-chloro-6- (naphthalen-2-yl) -2-phenylpyrimidine-5- 39.9 mmol of carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 18.8 g of compound 3 (yield 74%).

MS[M+H]+ = 638

production example 1-4. Synthesis of compound 4

Spiro [fluorene-9,9'-xanthine] -3'-ylboronic acid 15 g (39.9 mmol), 4-chloro-2- (dibenzo [b, d] thiophen-3-yl) - 39.9 mmol of 6-phenylpyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 21.9 g of compound 4 (yield 79%).

MS[M+H]+ = 694

production example 1-5. Synthesis of compound 5

Spiro [fluorene-9,9'-xanthine] -3'-ylboronic acid 15 g (39.9 mmol), 4-chloro-2,6-bis (phenyl-d5) pyrimidine-5-carbonitrile 39.9 mmol, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20 g of compound 5 (yield 84%).

MS[M+H]+ = 598

production example 1-6. Synthesis of compound 6

Spiro [fluorene-9,9'-xanthine] -4'-ylboronic acid 15 g (39.9 mmol), 4-chloro-6- (3- (phenanthren-9-yl) phenyl) -2- 39.9 mmol of phenylpyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 23.1 g of compound 6 (yield 76%).

MS[M+H]+ = 764

production example 1-7. Synthesis of compound 7

Spiro [fluorene-9,9'-xanthine]-4'-ylboronic acid 15 g (39.9 mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro- 39.9 mmol of 6-phenylpyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.4 g of compound 7 (yield 77%).

MS[M+H]+ = 664

production example 1-8. Synthesis of compound 8

Spiro [fluorene-9,9'-xanthine]-2-ylboronic acid 15 g (39.9 mmol), 4-chloro-2,6-diphenylpyrimidine-5-carbonitrile 39.9 mmol, tetrahydrofuran 150 mL and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 19.0 g of compound 8 (yield 81%).

MS[M+H]+ = 588

production example 1-9. Synthesis of compound 9

Spiro [fluorene-9,9'-xanthine]-3-ylboronic acid 15 g (39.9 mmol), 4-chloro-2-phenyl-6- (4-phenylnaphthalen-1-yl) pyrimidine- 39.9 mmol of 5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 21.3 g of compound 9 (yield 75%).

MS[M+H]+ = 714

production example 1-10. Synthesis of compound 10

Spiro [fluorene-9,9'-xanthine]-4-ylboronic acid 15 g (39.9 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6 -Phenylpyrimidine-5-carbonitrile 39.9 mmol, tetrahydrofuran 150 mL, and water 75 mL were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 19.1 g of compound 10 (yield 72%).

MS[M+H]+ = 664

production example 1-11. Synthesis of compound 11

Spiro [fluorene-9,9'-xanthine] -2'-ylboronic acid 15 g (39.9 mmol), 4-([1,1'-biphenyl]-4-yl)-2-(4 -Bromophenyl)-6-phenylpyrimidine-5-carbonitrile 39.9 mmol, tetrahydrofuran 150 mL, and water 75 mL were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 21.8 g of compound 11 (yield 74%).

MS[M+H]+ = 740

production example 1-12. Synthesis of compound 12

Spiro [fluorene-9,9'-thioxanthine] -4-ylboronic acid 15.7 g (39.9 mmol), 2-chloro-4-phenyl-6- (4-phenylnaphthalen-1-yl) pyri 39.9 mmol of midine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.7 g of compound 12 (yield 71%).

MS[M+H]+ = 730

production example 1-13. Synthesis of compound 13

Spiro [fluorene-9,9'-thioxanthin] -3'-ylboronic acid 15.7 g (39.9 mmol), 2- (4-bromophenyl) -4- (naphthalen-1-yl)- 39.9 mmol of 6-phenylpyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.4 g of compound 13 (yield 70%).

MS[M+H]+ = 730

production example 1-14. Synthesis of compound 14

Spiro[fluorene-9,9'-xanthine]-3-ylboronic acid 15 g (39.9 mmol), 2-(3-bromophenyl)-4-(naphthalen-2-yl)-6-phenyl 39.9 mmol of pyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.8 g of compound 14 (yield 73%).

MS[M+H]+ = 714

production example 1-15. Synthesis of compound 15

Spiro[fluorene-9,9'-thioxanthine]-2-ylboronic acid 15.7 g (39.9 mmol), 2-(3-bromophenyl)-4-(naphthalen-1-yl)-6 -Phenylpyrimidine-5-carbonitrile 39.9 mmol, tetrahydrofuran 150 mL, and water 75 mL were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.7 g of compound 15 (yield 71%).

MS[M+H]+ = 730

production example 1-16. Synthesis of compound 16

Spiro [fluorene-9,9'-xanthine] -2'-ylboronic acid 15 g (39.9 mmol), 4- (4-bromophenyl) -2,6-diphenylpyrimidine-5-carbonite 39.9 mmol of reel, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 22.0 g of compound 16 (yield 83%).

MS[M+H]+ = 664

production example 1-17. Synthesis of compound 17

Spiro [fluorene-9,9'-thioxanthine]-3'-ylboronic acid 15.7 g (39.9 mmol), 2-([1,1'-biphenyl]-3-yl)-4- 39.9 mmol of chloro-6-phenylpyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 21.2 g of compound 17 (yield 78%).

MS[M+H]+ = 680

production example 1-18. Synthesis of compound 18

Spiro [fluorene-9,9'-thioxanthine]-4'-ylboronic acid 15.7 g (39.9 mmol), 4-chloro-2,6-bis (phenyl-d5) pyrimidine-5-carbonite 39.9 mmol of reel, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 19.6 g of compound 18 (yield 80%).

MS[M+H]+ = 614

production example 1-19. Synthesis of compound 19

Spiro[fluorene-9,9'-thioxanthine]-2-ylboronic acid 15.7 g (39.9 mmol), 2-(3-(9H-carbazol-9-yl)phenyl)-4-chloro 39.9 mmol of -6-phenylpyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 23.3 g of compound 19 (yield 76%).

MS[M+H]+ = 769

production example 1-20. Synthesis of compound 20

Spiro [fluorene-9,9'-thioxanthine]-2-ylboronic acid 15.7 g (39.9 mmol), 4-chloro-2- (3- (7-cyano-9,9-dimethyl) -9H-fluoren-2-yl)phenyl)-6-phenylpyrimidine-5-carbonitrile 39.9 mmol, tetrahydrofuran 150 mL, and water 75 mL were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 23.3 g of compound 20 (yield 71%).

MS[M+H]+ = 821

production example 1-21. Synthesis of compound 21

Spiro[fluorene-9,9'-xanthine]-2-ylboronic acid 15 g (39.9 mmol), 4-(4-bromophenyl)-2,6-diphenylpyrimidine-5-carbonitrile 39.9 mmol, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.9 g of compound 21 (yield 79%).

MS[M+H]+ = 664

production example 1-22. Synthesis of compound 22

Spiro [fluorene-9,9'-xanthine] -3'-ylboronic acid 15 g (39.9 mmol), 4-([1,1'-biphenyl]-3-yl)-2-chloro- 39.9 mmol of 6-phenylpyrimidine-5-carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.4 g of compound 22 (yield 77%).

MS[M+H]+ = 664

production example 1-23. Synthesis of compound 23

Spiro [fluorene-9,9'-xanthine] -3'-ylboronic acid 15 g (39.9 mmol), 2-chloro-4- (naphthalen-2-yl) -6-phenylpyrimidine-5- 39.9 mmol of carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60 °C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 18.3 g of compound 23 (yield 72%).

MS[M+H]+ = 638

production example 1-24. Synthesis of compound 24

Spiro [fluorene-9,9'-xanthine]-2-ylboronic acid 15 g (39.9 mmol), 2-chloro-4- (phenanthren-2-yl)-6-phenylpyrimidine-5- 39.9 mmol of carbonitrile, 150 mL of tetrahydrofuran and 75 mL of water were mixed and heated to 60°C. Potassium carbonate (99.7 mmol) and tetrakistriphenylphosphine palladium (2 mmol) were added, and the mixture was stirred under reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with tetrahydrofuran and ethanol to obtain 20.8 g of Compound 24 (yield 76%).

MS[M+H]+ = 688

< Experimental example >

< Example 1>

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following compound [HI-A] was thermally vacuum-deposited to a thickness of 600 Å to form a hole injection layer. 50 Å and the following compound [HT-A] (600 Å) of hexanitrile hexaazatriphenylene (HAT) of the following formula were sequentially vacuum-deposited on the hole injection layer to form first and second hole transport layers.

Then, the following compounds [BH] and [BD] were vacuum-deposited in a weight ratio of 25:1 to a thickness of 200 Å on the hole transport layer to form a light emitting layer. On the light emitting layer, the compound 1 and [LiQ] (Lithiumquinolate) were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer to a thickness of 350 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.9 Å, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1 Х 10 ^-7 To maintain ~ 5 Х 10 ^-8 torr, an organic light emitting device was manufactured.

< Example 2 to 24>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compounds 2 to 24 were used instead of Compound 1 in Example 1.

< comparative example 1 to 4>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the following compounds ET1 to ET4 were used instead of Compound 1 in Example 1.

As in Examples 1 to 24 and Comparative Examples 1 to 4, the organic light emitting device prepared by using each compound as an electron injection and transport layer material was measured for driving voltage and luminous efficiency at a current density of ^{10 mA/cm 2 ,} At a current density of 20 mA/cm ² , a time (T98) of 98% of the initial luminance was measured.

The results are shown in Table 1 below.

division compound
(electron transport layer) Voltage
(V) efficiency
(cd/A) T ₉₈
(hr) Example 1 One 3.64 5.8 75 Example 2 2 3.60 5.6 80 Example 3 3 3.65 5.7 77 Example 4 4 3.61 5.6 82 Example 5 5 3.64 5.8 79 Example 6 6 3.61 5.5 76 Example 7 7 3.62 5.7 80 Example 8 8 3.62 5.8 77 Example 9 9 3.65 5.5 75 Example 10 10 3.64 5.7 76 Example 11 11 3.63 5.6 79 Example 12 12 3.61 5.6 77 Example 13 13 3.60 5.7 79 Example 14 14 3.62 5.6 81 Example 15 15 3.61 5.8 80 Example 16 16 3.63 5.5 78 Example 17 17 3.61 5.7 75 Example 18 18 3.64 5.7 75 Example 19 19 3.62 5.6 76 Example 20 20 3.61 5.5 79 Example 21 21 3.61 5.7 80 Example 22 22 3.60 5.8 80 Example 23 23 3.64 5.6 75 Example 24 24 3.63 5.6 78 Comparative Example 1 ET1 3.88 4.2 49 Comparative Example 2 ET2 3.85 4.1 53 Comparative Example 3 ET3 3.87 3.9 51 Comparative Example 4 ET4 3.81 4.2 38

From the experimental data of Table 1, it can be seen that the organic light emitting device using the compound of Formula 1 according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage and/or stability.

Comparative Example 1 using the compound ET-1 not containing a nitrile group as an electron transport layer material has a significantly shorter lifespan, a higher voltage, and lower efficiency than Examples 1 to 24 using a compound in which a nitrile group is bonded to an N-containing monocyclic ring. have.

Comparative Examples 2 and 3 using the compounds ET-2 and ET-3 in which the nitrile group is bonded to the core, not the N-containing monocyclic ring, respectively, are compared with Examples 1 to 24 .

Comparative Example 4 using the compound ET-4 in which a nitrile group is bonded to another substituent of the core has the shortest lifespan among Comparative Examples. Through this, it can be seen that there is a difference in voltage, efficiency, and especially lifespan when applied to an organic device according to the position of the nitrile substituent in the same core structure. It can be seen that when a compound in which a nitrile group is bonded to an N-containing monocyclic ring is used as the electron transport layer material, like the compound of the present invention, it has excellent electron transport ability and can realize a low voltage and high efficiency organic light emitting device.

1: Substrate
2: Anode
3: organic layer
4: cathode
5: hole injection layer
6: first hole transport layer
7: second hole transport layer
8: light emitting layer
9: Electron injection and transport layer

Claims (7)

Heterocyclic compound of formula (1):
[Formula 1]

In Formula 1,
X is O or S;
At least one of A1 to A16 is of Formula 2 below, and the rest is hydrogen,
[Formula 2]

In Formula 2,
The dotted line is a portion connected to at least any one of A1 to A16 of Formula 1,
one of B1 or B2 is -CCN, the other is N,
R1 and R2 are the same as or different from each other, and are each independently an aryl group unsubstituted or substituted with deuterium, CN, an alkyl group, a haloalkyl group, a haloalkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ; a silyl group unsubstituted or substituted with deuterium, CN, an alkyl group, or an aryl group; Or a heterocyclic group unsubstituted or substituted with deuterium, CN, an alkyl group, or a substituted or unsubstituted aryl group,
L is a direct bond; an arylene group unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group; Or an alkyl group, an aryl group, a heterocyclic group, and a divalent heterocyclic group unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group substituted with an alkyl group,
n is an integer from 1 to 3,
When n is 2 or more, L of 2 or more are the same as or different from each other. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 1-1 to 1-8:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

In Formulas 1-1 to 1-8, B1, B2, R1, R2, X, L, and n are as defined in Formula 1 above. The method according to claim 1, wherein R1 and R2 are the same as or different from each other, and independently represent an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms, and the aryl group having 6 to 20 carbon atoms or 3 to 20 carbon atoms. The heteroaryl group is substituted with any one or more substituents selected from deuterium, CN, an alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms Or an unsubstituted heterocyclic compound. The method according to claim 1, wherein L is a direct bond; phenylene group; biphenylene group; anthracenylene group; phenanthrenylene group; Or a heterocyclic compound that is naphthylene. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following structures:

a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one organic material layer of the organic material layer contains the heterocyclic compound according to any one of claims 1 to 5. light emitting element. 7. The method of claim 6,
The organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers includes a heterocyclic compound represented by Formula 1 above. device.

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