KR102643077B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

This specification relates to the compound of Formula 1 and an organic light-emitting device containing the same.

Description

Heterocyclic compound and organic light-emitting device containing the same {HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This specification relates to heterocyclic compounds and organic light-emitting devices containing the same.

The present invention claims the benefit of Korean Patent Application No. 10-2020-0071710 filed with the Korea Intellectual Property Office on June 12, 2020, the entire contents of which are incorporated herein by reference.

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

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device. For example, it consists of a hole injection layer, a hole transport layer, a light-emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer. You can lose. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows. These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as organic layers in organic light-emitting devices can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, and electron injection materials, depending on their function. Depending on the color of the light, there are blue, green, and red light emitting materials, as well as yellow and orange light emitting materials needed to achieve better natural colors.

Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. The principle is that when a small amount of dopant, which has a smaller energy band gap and higher luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the host are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

In order to fully demonstrate the excellent characteristics of the above-described organic light-emitting device, the materials that make up the organic layer within the device, such as hole injection material, hole transport material, light-emitting material, electron suppressor material, electron transport material, and electron injection material, must be stable and efficient materials. As this is supported by , the development of new materials continues to be required.

International Patent Publication No. 2017-126443

Described herein are heterocyclic compounds and organic light-emitting devices containing the same.

An exemplary embodiment of the present specification provides a heterocyclic compound of the following formula (1).

[Formula 1]

In Formula 1,

R1 to R10 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

At least one of R1 to R10 is any one of the following formulas 2-1 to 2-3,

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

The dotted line is a portion connected to Formula 1,

L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Substituted or unsubstituted alkenylene group; A substituted or unsubstituted divalent fluorene group; Or a substituted or unsubstituted heteroarylene group,

m1 and m2 are each integers from 0 to 5,

When m1 is 2 or more, the L1 are the same or different from each other,

When m2 is 2 or more, the L2 are the same or different,

At least one of X1 to X3 is N, and the remainder is CRa,

Ra are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar1 to Ar3 are The same or different from each other, each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heteroaryl group,

a is an integer from 0 to 3,

When a is 2 or more, Ar3 is the same or different from each other,

[Formula 2-3]

In Formula 2-3,

The dotted line is a portion connected to Formula 1,

Y3 is O, S, NRj or CRkRl,

X12 and X13 are the same or different from each other and are each independently N or CRm,

Rj to Rm are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L7 is a direct bond; Substituted or unsubstituted arylene group; Substituted or unsubstituted alkenylene group; A substituted or unsubstituted divalent fluorene group; Or a substituted or unsubstituted heteroarylene group,

m7 is an integer from 0 to 5,

When m7 is 2 or more, the L7 are the same or different from each other,

Ar9 is hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heteroaryl group.

Additionally, according to an exemplary embodiment of the present invention, a first electrode; a second electrode provided opposite the first electrode; and an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the above-mentioned compounds.

The compound of the present invention can be used as a material for the organic layer of an organic light-emitting device. When manufacturing an organic light-emitting device including the compound of the present invention, an organic light-emitting device with high efficiency, low voltage, and long lifespan characteristics can be obtained, and when the compound of the present invention is included in the light-emitting layer of the organic light-emitting device, high color gamut can be achieved. Eggplant can manufacture organic light-emitting devices.

1 and 2 show examples of organic light-emitting devices according to the present invention.

Hereinafter, this specification will be described in more detail.

The present specification provides a heterocyclic compound represented by Formula 1 above. When the heterocyclic compound represented by Formula 1 is used in the organic material layer of an organic light-emitting device, the efficiency and lifespan characteristics of the organic light-emitting device are improved.

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.

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

Examples of substituents in this 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 changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same 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; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted heteroaryl groups, or substituted with a substituent in which two or more of the above-exemplified substituents are linked, or having no substituent. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

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

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

In the present specification, the silyl group may be represented by the formula -SiYaYbYc, where Ya, Yb, and Yc are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.

In the present specification, the boron group may be represented by the chemical formula -BY4Y5, where Y4 and Y5 are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.

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

In this specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine group and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine groups; 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-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., but is not limited thereto.

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

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

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

In this specification, the alkyl groups in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group are the same as examples of the alkyl groups described above. Specifically, the alkylthioxy group includes methylthioxy group; ethylthioxy group; tert-butylthioxy group; hexylthioxy group; Octylthioxy groups, etc., and examples of alkylsulfoxy groups include mesyl; ethyl sulfoxy group; Propyl alcohol oxygen group; Butyl sulfoxy group, etc., 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 one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., 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 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 monocyclic aryl group, such as a phenyl group, biphenyl group, or terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorene group, etc., but is not limited thereto.

In the present specification, the heteroaryl group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 2 to 30 carbon atoms. Examples of heteroaryl groups include pyridine group, pyrrole group, pyrimidine group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, carbazole group, etc. However, it is not limited to these.

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

According to an exemplary embodiment of the present specification, at least one of R1 to R10 is of the following formula 2-1 or 2-2.

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

The dotted line is a portion connected to Formula 1,

L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Substituted or unsubstituted alkenylene group; A substituted or unsubstituted divalent fluorene group; Or a substituted or unsubstituted heteroarylene group containing one or more of N, O, S and P,

m1 and m2 are each integers from 0 to 5,

When m1 is 2 or more, the L1 are the same or different from each other,

When m2 is 2 or more, the L2 are the same or different,

At least one of X1 to X3 is N, and the remainder is CRa,

Ra are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar1 to Ar3 are The same or different from each other, each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heteroaryl group,

a is an integer from 0 to 3,

When a is 2 or more, Ar3 is the same as or different from each other.

According to an exemplary embodiment of the present specification, at least one of R1 to R10 is of the following formula 2-3.

[Formula 2-3]

In Formula 2-3,

The dotted line is a portion connected to Formula 1,

Y3 is O, S, NRj or CRkRl,

X12 and X13 are the same or different from each other and are each independently N or CRm,

Rj to Rm are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

L7 is a direct bond; Substituted or unsubstituted arylene group; Substituted or unsubstituted alkenylene group; A substituted or unsubstituted divalent fluorene group; Or a substituted or unsubstituted heteroarylene group containing one or more of N, O, S and P,

m7 is an integer from 0 to 5,

When m7 is 2 or more, the L7 are the same or different from each other,

Ar9 is hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, R1 to R4 are hydrogen.

According to an exemplary embodiment of the present specification, R5 to R10 are hydrogen.

According to an exemplary embodiment of the present specification, the substituent of R1 to R10 that is not one of Formulas 2-1 to 2-3 is hydrogen.

According to an exemplary embodiment of the present specification, at least one of X1 to X3 is N, and the others are CRa.

According to an exemplary embodiment of the present specification, at least two of X1 to X3 are N, and the remainder are CRa.

According to an exemplary embodiment of the present specification, among X1 to X3, X1 is N and the rest are CRa.

According to an exemplary embodiment of the present specification, among X1 to X3, X2 is N, and the remainder is CRa.

According to an exemplary embodiment of the present specification, among X1 to X3, X3 is N, and the remainder is CRa.

According to an exemplary embodiment of the present specification, among X1 to X3, X1 and X2 are N, and X3 is CRa.

According to an exemplary embodiment of the present specification, among X1 to X3, X1 and X3 are N, and X2 is CRa.

According to an exemplary embodiment of the present specification, among X1 to X3, X3 and X2 are N, and X1 is CRa.

According to an exemplary embodiment of the present specification, X1 to X3 are N.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted heteroarylene group containing one or more of N, O, S and P.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms containing one or more of N, O, S, and P.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms containing one or more of N, O, S, and P.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Arylene group substituted or unsubstituted with an alkyl group; Or it is a heteroarylene group containing one or more of N, O and S.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; An arylene group having 6 to 20 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; Or it is a heteroarylene group having 3 to 20 carbon atoms containing one or more of N, O, and S.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently a direct bond.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent terphenyl group, a divalent dimethylfluorene group, or 2 It is an anthracene group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a divalent furan group, a divalent thiophene group, a divalent dibenzofuran group, a divalent dibenzothiophene group, or It is a divalent pyridine group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent terphenyl group, and a divalent dimethylfluorene group. , a divalent anthracene group, a divalent furan group, a divalent thiophene group, a divalent dibenzofuran group, a divalent dibenzothiophene group, or a divalent pyridine group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a divalent furan group, a divalent thiophene group, or a divalent pyridine group.

According to an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent furan group, a divalent thiophene group, Or it is a divalent pyridine group.

According to an exemplary embodiment of the present specification, when m1 is 2 or more, L1 is a form in which arylene groups having 6 to 30 carbon atoms are sequentially bonded. For example, it is in the form of -(phenyl)-(naphthyl)-.

According to an exemplary embodiment of the present specification, when m1 is 2 or more, L1 is an arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted group of 3 to 30 carbon atoms including one or more of N, O, S, and P. It is a form in which heteroarylene groups are sequentially bonded. For example, -(phenyl)-(furan)-, or -(pyridine)-(naphthyl)-.

According to an exemplary embodiment of the present specification, when m1 is 2 or more, L1 is a form in which substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms including one or more of N, O, S, and P are sequentially bonded. am. For example, -(furan)-(pyridine)-, or -(pyridine)-(dibenzofuran)-.

According to an exemplary embodiment of the present specification, when m2 is 2 or more, L2 is a form in which arylene groups having 6 to 30 carbon atoms are sequentially bonded. For example, it is in the form of -(phenyl)-(naphthyl)-.

According to an exemplary embodiment of the present specification, when m2 is 2 or more, L2 is a substituted or unsubstituted group of 3 to 30 carbon atoms including an arylene group of 6 to 30 carbon atoms and one or more of N, O, S, and P. It is a form in which heteroarylene groups are sequentially bonded. For example, -(phenyl)-(furan)-, or -(pyridine)-(naphthyl)-.

According to an exemplary embodiment of the present specification, when m2 is 2 or more, L2 is a form in which substituted or unsubstituted heteroarylene groups having 3 to 30 carbon atoms including one or more of N, O, S, and P are sequentially bonded. am. For example, -(furan)-(pyridine)-, or -(pyridine)-(dibenzofuran)-.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted fluorene group; or a substituted or unsubstituted heteroaryl group containing one or more of N, O, S, and P atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted fluorene group; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms and containing one or more of N, O, S, and P atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Substituted or unsubstituted fluorene group; or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms and containing one or more of N, O, S, and P atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, di It is a benzofuran group, a dibenzothiophene group, or a pyridine group,

The phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, dibenzofuran group, dibenzothiophene group, or pyridine group is deuterium, nitrile group, substituted or unsubstituted. It is substituted or unsubstituted with an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, di It is a benzofuran group, a dibenzothiophene group, or a pyridine group,

The phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, dibenzofuran group, dibenzothiophene group, or pyridine group is deuterium, nitrile group, alkyl group, or aryl group. , an aryl group substituted with an aryl group, an aryl group substituted with an alkyl group, an aryl group substituted with a heteroaryl group, an aryl group substituted with a nitrile group, a heteroaryl group substituted with an aryl group, a heteroaryl group substituted with a heteroaryl group, and a heteroaryl group. It is substituted or unsubstituted with one or more substituents selected from among.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, di It is a benzofuran group, a dibenzothiophene group, or a pyridine group,

The phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, dibenzofuran group, dibenzothiophene group, or pyridine group is a nitrile group, methyl group, phenyl group, or naphthyl group. , a biphenyl group, a phenyl group substituted with a nitrile group, a naphthyl group substituted with a nitrile group, and a biphenyl group substituted with a nitrile group.

According to an exemplary embodiment of the present specification, Ra and Rj to Rm are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Alkyl group; Cycloalkyl group; Aryl group; or a heteroaryl group containing one or more of N, O, S, and P atoms.

According to an exemplary embodiment of the present specification, Ra is hydrogen or deuterium.

According to an exemplary embodiment of the present specification, Ra is hydrogen.

According to an exemplary embodiment of the present specification, Rj to Rm are hydrogen.

According to an exemplary embodiment of the present specification, Y3 is O.

According to an exemplary embodiment of the present specification, Y3 is S.

According to an exemplary embodiment of the present specification, Y3 is N.

According to an exemplary embodiment of the present specification, Y3 is CRkRl.

According to an exemplary embodiment of the present specification, L7 is a direct bond; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted heteroarylene group containing one or more of N, O, S and P.

According to an exemplary embodiment of the present specification, L7 is a direct bond; Arylene group; Or it is a heteroarylene group containing one or more of N, O and S.

According to an exemplary embodiment of the present specification, L7 is a direct bond; Arylene group having 6 to 20 carbon atoms; Or it is a heteroarylene group having 3 to 20 carbon atoms containing one or more of N, O, and S.

According to an exemplary embodiment of the present specification, L7 is a direct bond.

According to an exemplary embodiment of the present specification, L7 is a phenylene group, a divalent biphenyl group, or a divalent naphthyl group.

According to an exemplary embodiment of the present specification, L7 is a divalent furan group, a divalent thiophene group, or a divalent pyridine group.

According to an exemplary embodiment of the present specification, L7 is a direct bond, a phenylene group, a divalent biphenyl group, a divalent naphthyl group, a divalent furan group, a divalent thiophene group, or a divalent pyridine group.

According to an exemplary embodiment of the present specification, Ar3 and Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted fluorene group; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms and containing one or more of N, O, S, and P atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar9 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Substituted or unsubstituted fluorene group; or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms and containing one or more of N, O, S, and P atoms.

According to an exemplary embodiment of the present specification, Ar3 and Ar9 are the same as or different from each other, and are each independently phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, di It is a benzofuran group, a dibenzothiophene group, or a pyridine group,

The phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, dibenzofuran group, dibenzothiophene group, or pyridine group is deuterium, nitrile group, substituted or unsubstituted. It is substituted or unsubstituted with an alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Ar3 and Ar9 are the same as or different from each other, and are each independently phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, di It is a benzofuran group, a dibenzothiophene group, or a pyridine group,

The phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, dibenzofuran group, dibenzothiophene group, or pyridine group is deuterium, nitrile group, alkyl group, or aryl group. , an aryl group substituted with an aryl group, an aryl group substituted with an alkyl group, an aryl group substituted with a heteroaryl group, an aryl group substituted with a nitrile group, a heteroaryl group substituted with an aryl group, a heteroaryl group substituted with a heteroaryl group, and a heteroaryl group. It is substituted or unsubstituted with any one selected from among.

According to an exemplary embodiment of the present specification, Ar3 and Ar9 are the same as or different from each other, and are each independently phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, di It is a benzofuran group, a dibenzothiophene group, or a pyridine group,

The phenyl group, biphenyl group, terphenyl group, naphthyl group, fluoranthene group, phenalene group, phenanthrene group, fluorene group, dibenzofuran group, dibenzothiophene group, or pyridine group is a nitrile group, methyl group, phenyl group, or naphthyl group. , a biphenyl group, a phenyl group substituted with a nitrile group, a naphthyl group substituted with a nitrile group, and a biphenyl group substituted with a nitrile group.

In an exemplary embodiment of the present specification, Formula 1 is any one selected from the following structures.

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

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 adjusted by introducing various substituents into the core structure of the above structure.

In addition, by introducing various substituents into the core structure of the above structure, it is possible to synthesize compounds having the unique properties of the introduced substituents. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, a material that satisfies the conditions required for each organic material layer can be synthesized. You can.

Additionally, the organic light emitting device according to the present invention includes a first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the above-described compound.

The organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.

The heterocyclic 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 application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or 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 performs hole injection and hole transport, 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 to this and may include fewer or more organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers includes a heterocyclic compound represented by Formula 1 can do.

In the organic light emitting device of the present invention, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes the heterocyclic compound.

In the organic light emitting device of the present invention, the organic material layer includes an electron transport layer, and the electron transport layer includes the heterocyclic compound.

In the organic light emitting device of the present invention, the organic material layer includes an electron injection and transport layer, and the electron injection and transport layer includes the heterocyclic compound.

In the organic light emitting device of the present invention, the organic material layer includes an electron injection and transport layer, and the electron injection and transport layer includes the heterocyclic compound of Formula 1 and a metal complex.

According to an exemplary embodiment of the present specification, the electron injection and transport layer includes the heterocyclic compound of Formula 1 and LiQ (Lithiumquinolate) at a weight ratio of 1:99 to 99:1.

According to an exemplary embodiment of the present specification, the electron injection and transport layer includes the heterocyclic compound of Formula 1 and LiQ (Lithiumquinolate) at a weight ratio of 1:9 to 9:1.

According to an exemplary embodiment of the present specification, the electron injection and transport layer includes the heterocyclic compound of Formula 1 and LiQ (Lithiumquinolate) at a weight ratio of 2:8 to 8:2.

According to an exemplary embodiment of the present specification, the electron injection and transport layer includes the heterocyclic compound of Formula 1 and LiQ (Lithiumquinolate) at a weight ratio of 4:6 to 6:4.

According to an exemplary embodiment of the present specification, the electron injection and transport layer includes the heterocyclic compound of Formula 1 and LiQ (Lithiumquinolate) in a 1:1 weight ratio.

In the organic light emitting device of the present invention, the organic material layer may include one or more layers among a hole injection layer, a hole transport layer, and a layer that performs both hole injection and hole transport, and one or more of the layers is represented by the formula (1) Contains heterocyclic compounds.

In the organic light-emitting device of the present invention, the organic material layer includes a light-emitting layer, and the light-emitting layer includes a host material and a dopant material.

In the organic light emitting device of the present invention, the light emitting layer includes a host material and a dopant material at a weight ratio of 1:99 to 99:1.

In the organic light emitting device of the present invention, the light emitting layer includes a host material and a dopant material at a weight ratio of 1:99 to 90:10.

In the organic light emitting device of the present invention, the light emitting layer includes a host material and a dopant material at a weight ratio of 1:99 to 50:50.

In the organic light emitting device of the present invention, the light emitting layer includes a host material and a dopant material at a weight ratio of 30:1 to 99:1.

An organic light-emitting device according to an exemplary embodiment of the present specification includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following formula H as a host material.

[Formula H]

In the formula H,

L21 to L23 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R21 to R27 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar21 to Ar23 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

k is 0 or 1.

In an exemplary embodiment of the present specification, when k is 0, hydrogen or deuterium is connected to the position of -L23-Ar23.

In an exemplary embodiment of the present specification, R21 to R27 are the same as or different from each other, and are each independently hydrogen or deuterium.

In an exemplary embodiment of the present specification, Ar21 and Ar22 are different from each other.

In one embodiment of the present specification, Ar21 is a substituted or unsubstituted heteroaryl group, and Ar22 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar21 is a dibenzofuran group, and Ar22 is a phenyl group.

In an exemplary embodiment of the present specification, L21 to L23 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or it is a substituted or unsubstituted dibenzothiophene group.

An organic light-emitting device according to an exemplary embodiment of the present specification includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following formula D as a dopant material.

[Formula D]

In Formula D,

E1 to E3 are the same or different from each other and are each independently an aromatic hydrocarbon ring,

R34 to R38 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted amine group; or a substituted or unsubstituted heterocyclic group; Or, it combines with an adjacent group to form a substituted or unsubstituted ring,

n4 and n5 are each an integer of 1 to 4, n6 is an integer of 1 to 3, n7 and n8 are each an integer of 1 to 5, and when n4 to n8 are each 2 or more, 2 or more substituents in parentheses are the same or Different.

In an exemplary embodiment of the present specification, E1 to E3 are the same or different from each other and are each independently a benzene ring or a naphthyl ring.

In an exemplary embodiment of the present specification, R34 to R38 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is an alkyl group having 1 to 10 carbon atoms.

In one 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 suppression layer/electron transport layer/cathode

(15) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode

(17) Anode/hole injection layer/hole transport layer/light-emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(18) Anode/hole injection layer/hole transport layer/electron suppression 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 same structure as shown in FIG. 1, but is not limited thereto.

The structure of the organic light emitting device of the present invention may have the same structure as shown in FIG. 2, but is not limited thereto.

Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1. In this structure, the heterocyclic compound represented by Formula 1 may be included in the organic layer 3.

In Figure 2, a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron injection and transport layer 8, and a second electrode 4 are sequentially placed on the substrate 1. The structure of a stacked organic light emitting device is illustrated. In this structure, the heterocyclic compound represented by Formula 1 may be included in the electron injection and transport layer (8).

For example, the organic light emitting device according to the present invention deposits a metal, a conductive metal oxide, or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. An anode is formed by depositing a layer on which a hole injection layer, a hole transport layer, a layer that simultaneously performs hole transport and hole injection, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that performs both electron transport and electron injection are selected from the group consisting of It can be manufactured by forming an organic material layer containing one or more selected layers and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, but is not limited to this and may have a single-layer structure. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.

The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials 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); Combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series conductive polymers, etc., but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.

The hole transport layer may play a role in facilitating the transport of holes. The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and includes 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 suppressing layer may be made of the spiro compound described above 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 range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.

Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

When the light-emitting layer emits red light, the light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium). ), phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these. If the light-emitting 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) can be used as the light-emitting dopant. However, it is not limited to this. If the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.

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

The electron transport layer may play a role in facilitating the transport of electrons. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. 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 in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.

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

Examples of the metal complex compounds 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-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.

The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.

The organic light emitting device of the present invention can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.

The method for producing the heterocyclic compound of Formula 1 and the production of organic light-emitting devices using the same will be described in detail in the examples below. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

In the following reaction formula, various types of intermediates can be synthesized by appropriately selecting starting materials known to those skilled in the art regarding the type and number of substituents. Reaction types and reaction conditions known in the art can be used.

Preparation Example 1-1 <Preparation of Compound C1>

Compound P1-A (35.0 g, 105 mmol) and compound B (32.0 g, 126 mmol) were added to 600 ml of dioxane and stirred in a nitrogen atmosphere. Afterwards, potassium acetate (43.5 g, 315 mmol) was added, the temperature was gradually raised to reflux, and 100 ml of dioxane was distilled under reduced pressure. Afterwards, [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (Pd(dppf)Cl ₂ , 1.53g, 2.1mmol) was added. After reaction for 2 hours, it was cooled to room temperature, and acetonitrile and water were added to precipitate a solid. After filtering the resulting solid, it was dissolved in 340 ml of chloroform at room temperature, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate and acidic clay were added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The solid produced by concentration was filtered to prepare a pale ivory colored solid compound P1 (29.5 g, yield 73%, MS: [M+H]+=381).

Compound P1 (16.0 g, 42.1 mmol) and Compound A1 (11.3 g, 42.1 mmol) were added to 200 ml of tetrahydrofuran and stirred in a nitrogen atmosphere. Afterwards, potassium carbonate (17.4 g, 126.24 mmol) was dissolved in 70 ml of water, stirred sufficiently, and then gradually heated to reflux. Afterwards, tetrakis(triphenylphosphine)palladium (1.46g, 1.26mmol) was added. After reaction for 12 hours, it was cooled to room temperature and the resulting solid was filtered. The filtered solid was dissolved in 980 ml of N-methyl-2-pyrrolidone at 130°C, and 4 ml of diethylenetriamine was added and stirred. After cooling to room temperature, the resulting solid was filtered and the process was repeated one more time. Afterwards, slurry purification was performed using toluene and tetrahydrofuran respectively to prepare white solid compound C1 (14.1 g, yield 69%, MS: [M+H]+=486).

Preparation Example 1-2 <Preparation of Compound C2>

Compound C2 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(23.7g, yield 59%, MS: [M+H] ⁺ = 562)

Preparation Example 1-3 <Preparation of Compound C3>

Compound C3 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

(18.2g, yield 60%, MS: [M+H] ⁺ = 652)

Preparation Example 1-4 <Preparation of Compound C4>

Compound C4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(24.4g, yield 63%, MS: [M+H] ⁺ = 587)

Preparation Example 1-5 <Preparation of Compound C5>

Compound C5 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(30.4g, yield 76%, MS: [M+H] ⁺ = 562)

Preparation Example 1-6 <Preparation of Compound C6>

Compound C6 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(29.5g, yield 73%, MS: [M+H] ⁺ = 562)

Preparation Example 1-7 <Preparation of Compound C7>

Compound C7 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(25.8g, yield 64%, MS: [M+H] ⁺ = 714)

Preparation Example 1-8 <Preparation of Compound C8>

Compound C8 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(32.0g, yield 80%, MS: [M+H] ⁺ = 562)

Preparation Example 1-9 <Preparation of Compound C9>

Compound C9 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(21.1g, yield 52%, MS: [M+H] ⁺ = 652)

Preparation Example 1-10 <Preparation of Compound C10>

Compound C10 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

(17.4g, yield 58%, MS: [M+H] ⁺ = 638)

Preparation Example 1-11 <Preparation of Compound C11>

Compound C11 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(18.2g, yield 60%, MS: [M+H] ⁺ = 688)

Preparation Example 1-12 <Preparation of Compound C12>

Compound C12 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(31.3g, yield 78%, MS: [M+H] ⁺ = 562)

Preparation Example 1-13 <Preparation of Compound C13>

Compound C13 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(20.3g, 50% yield, MS: [M+H] ⁺ = 652)

Preparation Example 1-14 <Preparation of Compound C14>

Compound C14 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(21.0g, yield 70%, MS: [M+H] ⁺ = 562)

Preparation Example 1-15 <Preparation of Compound C15>

Compound C15 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(17.4g, yield 58%, MS: [M+H] ⁺ = 612)

Preparation Example 1-16 <Preparation of Compound C16>

Compound C16 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(12.1g, yield 40%, MS: [M+H] ⁺ = 663)

Preparation Example 1-17 <Preparation of Compound C17>

Compound C17 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(23.3g, yield 77%, MS: [M+H] ⁺ = 638)

Preparation Example 1-18 <Preparation of Compound C18>

Compound C18 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(14.0g, yield 46%, MS: [M+H] ⁺ = 563)

Preparation Example 1-19 <Preparation of Compound C19>

Compound C19 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

(22.2g, yield 74%, MS: [M+H] ⁺ = 562)

Preparation Example 1-20 <Preparation of Compound C20>

Compound C20 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(15.6g, yield 52%, MS: [M+H] ⁺ = 638)

Preparation Example 1-21 <Preparation of Compound C21>

Compound C21 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

(10.3g, yield 34%, MS: [M+H] ⁺ = 703)

Preparation Example 1-22 <Preparation of Compound C22>

Compound C22 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(18.6g, yield 62%, MS: [M+H] ⁺ = 638)

Preparation Example 1-23 <Preparation of Compound C23>

Compound C23 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(20.4g, yield 68%, MS: [M+H] ⁺ = 637)

Preparation Example 1-24 <Preparation of Compound C24>

Compound C24 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(26.3g, yield 65%, MS: [M+H] ⁺ = 561)

Preparation Example 1-25 <Preparation of Compound C25>

Compound C25 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(17.3g, yield 69%, MS: [M+H] ⁺ = 561)

Preparation Example 1-26 <Preparation of Compound C26>

Compound C26 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(16.3g, yield 65%, MS: [M+H] ⁺ = 651)

Preparation Example 1-27 <Preparation of Compound C27>

Compound C27 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(13.8g, yield 46%, MS: [M+H] ⁺ = 662)

Preparation Example 1-28 <Preparation of Compound C28>

Compound C28 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(26.7g, yield 66%, MS: [M+H] ⁺ = 409)

Preparation Example 1-29 <Preparation of Compound C29>

Compound C29 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(19.7g, yield 49%, MS: [M+H] ⁺ = 485)

Preparation Example 1-30 <Preparation of Compound C30>

Compound C30 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(16.1g, yield 53%, MS: [M+H] ⁺ = 535)

Preparation Example 1-31 <Preparation of Compound C31>

Compound C31 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

(13.0g, yield 43%, MS: [M+H] ⁺ = 399)

Preparation Example 1-32 <Preparation of Compound C32>

Compound C32 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(14.4g, yield 48%, MS: [M+H] ⁺ = 474)

Preparation Example 1-33 <Preparation of Compound C33>

Compound C33 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

(14.6g, yield 48%, MS: [M+H] ⁺ = 422)

Preparation Example 1-34 <Preparation of Compound C34>

Compound C34 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(20.1g, yield 50%, MS: [M+H] ⁺ = 551)

Preparation Example 1-35 <Preparation of Compound C35>

Compound C35 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

(19.9g, yield 49%, MS: [M+H] ⁺ = 490)

Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.

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

Next, the following compounds [BH] and [BD] were vacuum deposited on the hole transport layer to a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer.

On the emitting layer, the compound C1 and the following compound [LiQ] (Lithiumquinolate) were vacuum deposited at a 1:1 weight ratio to form an electron injection and transport layer with 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 organic materials was maintained at 0.4 to 0.9 Å/sec, the lithium fluoride of the cathode was maintained at a deposition rate of 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 1x10 ^-7. An organic light emitting device was manufactured by maintaining torr of 5x10 ^-8 torr.

Examples 1-2 to 1-35

In Example 1-1, an organic light-emitting device was manufactured in the same manner as Example 1-1, except that the compounds in Table 1 below were used instead of Compound C1.

Comparative Examples 1-1 to 1-3

In Example 1-1, an organic light-emitting device was manufactured in the same manner as Example 1-1, except that the compounds in Table 1 below were used instead of compound C1.

The driving voltage and luminous efficiency of the organic light emitting device were measured at a current density of 10 mA/cm ² , and the time for the luminance to reach 90% of the initial luminance (T ₉₀ ) was measured at a current density of 20 mA/cm ² . The results are shown in Table 1 below.

compound
(electron injection and transport layer) Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) Color coordinates
(x,y) Lifespan (h)
T ₉₀ at 20mA/cm ² Example 1-1 C1 3.72 6.30 (0.133, 0.088) 197 Example 1-2 C2 3.66 6.42 (0.133, 0.088) 174 Example 1-3 C3 3.91 6.12 (0.133, 0.087) 166 Example 1-4 C4 3.66 5.98 (0.133, 0.088) 189 Examples 1-5 C5 3.79 5.71 (0.135, 0.087) 167 Example 1-6 C6 3.82 5.93 (0.133, 0.088) 163 Example 1-7 C7 3.81 6.12 (0.133, 0.088) 171 Examples 1-8 C8 3.90 6.43 (0.133, 0.087) 185 Example 1-9 C9 3.67 6.39 (0.133, 0.088) 211 Examples 1-10 C10 3.56 6.46 (0.133, 0.088) 192 Example 1-11 C11 3.88 6.50 (0.133, 0.088) 208 Examples 1-12 C12 3.73 6.42 (0.133, 0.088) 177 Example 1-13 C13 3.56 6.47 (0.133, 0.087) 175 Example 1-14 C14 3.64 6.33 (0.133, 0.088) 221 Example 1-15 C15 3.71 6.47 (0.133, 0.088) 189 Example 1-16 C16 3.69 6.38 (0.133, 0.088) 204 Example 1-17 C17 3.89 6.45 (0.133, 0.088) 212 Example 1-18 C18 3.72 6.33 (0.133, 0.087) 171 Example 1-19 C19 3.92 5.80 (0.133, 0.087) 160 Examples 1-20 C20 3.66 6.73 (0.133, 0.088) 161 Example 1-21 C21 3.79 6.31 (0.133, 0.088) 159 Example 1-22 C22 3.88 6.48 (0.133, 0.088) 168 Example 1-23 C23 3.71 5.80 (0.133, 0.088) 179 Example 1-24 C24 3.76 6.41 (0.133, 0.087) 195 Example 1-25 C25 3.61 6.50 (0.133, 0.088) 201 Example 1-26 C26 3.72 6.59 (0.133, 0.088) 191 Example 1-27 C27 3.76 6.21 (0.133, 0.088) 187 Example 1-28 C28 3.81 6.36 (0.133, 0.088) 163 Example 1-29 C29 3.90 6.31 (0.133, 0.087) 178 Example 1-30 C30 3.64 6.38 (0.133, 0.088) 195 Example 1-31 C31 3.87 6.47 (0.133, 0.088) 200 Example 1-32 C32 3.68 6.52 (0.133, 0.088) 171 Example 1-33 C33 3.62 6.53 (0.133, 0.088) 163 Example 1-34 C34 3.64 5.99 (0.133, 0.088) 181 Example 1-35 C35 3.81 6.18 (0.133, 0.088) 156 Comparative Example 1-1 ET-1 4.44 3.33 (0.133, 0.088) 66 Comparative Example 1-2 ET-2 4.57 3.29 (0.133, 0.087) 47 Comparative Example 1-3 ET-3 4.10 2.52 (0.133, 0.088) 72

As shown in Table 1, the heterocyclic compound represented by Formula 1 according to the present specification can be used in the electron injection and transport layer in the organic material layer of the organic light-emitting device.

Comparing Examples 1-1 to 1-35 and Comparative Examples 1-1 to 1-3 in Table 1, the formula 1 and formula 2-1, 2-2, or 2-3 according to the present specification When a compound containing a combination of monocyclic heteroaryl groups was used, it was confirmed that the organic light emitting devices of Comparative Examples 1-1 to 1-3, all of which had hydrogen or aryl groups combined, exhibited significantly superior characteristics in terms of voltage, efficiency, and lifespan.

1: substrate
2: first electrode
3: Organic layer
4: Second electrode
5: Hole injection layer
6: Hole transport layer
7: Light-emitting layer
8: Electron injection and transport layer

Claims (11)

Heterocyclic compound of formula 1:
[Formula 1]

In Formula 1,
At least one of R1 to R10 is any one of the following formulas 2-1 to 2-3, the others are the same or different from each other, and are each independently hydrogen; or deuterium,
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,
The dotted line is a portion connected to Formula 1,
L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
m1 and m2 are each integers from 0 to 5,
When m1 is 2 or more, the L1 are the same or different from each other,
When m2 is 2 or more, the L2 are the same or different,
At least one of X1 to X3 is N, and the remainder is CRa,
Ra are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar1 to Ar3 are The same or different from each other, each independently hydrogen; heavy hydrogen; halogen group; Nitrile group; nitro group; hydroxyl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted fluorene group; Or a substituted or unsubstituted heteroaryl group,
a is an integer from 0 to 3,
When a is 2 or more, Ar3 is the same or different from each other,
[Formula 2-3]

In Formula 2-3,
The dotted line is a portion connected to Formula 1,
Y3 is O, S, NRj or CRkRl,
X12 and X13 are the same or different from each other and are each independently N or CRm,
Rj to Rm are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
L7 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
m7 is an integer from 0 to 5,
When m7 is 2 or more, the L7 are the same or different from each other,
Ar9 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The heterocyclic compound according to claim 1, wherein at least one of R1 to R10 is of Formula 2-3. The heterocyclic compound according to claim 1, wherein at least one of R1 to R10 is of Formula 2-1 or 2-2. The method according to claim 1, wherein R1 to R4 are hydrogen. The heterocyclic compound according to claim 1, wherein R5 to R10 are hydrogen. The method according to claim 1, wherein L1 and L2 are the same or different from each other, and are each independently directly bonded; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a heterocyclic compound that is a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms containing one or more of N, O, S and P. The method according to claim 1, wherein Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted fluorene group; Or a heterocyclic compound that is a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms and containing one or more of N, O, S, and P atoms. The heterocyclic compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:







































































































first electrode; a second electrode provided opposite the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 8. . In claim 9,
The organic material layer includes an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, an electron injection layer, or an electron injection and transport layer includes the heterocyclic compound. In claim 9,
The organic material layer includes an electron injection and transport layer, and the electron injection and transport layer includes a heterocyclic compound of Formula 1 and a metal complex.