KR20220119318A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same. An exemplary embodiment of the present specification provides a compound represented by chemical formula 1. The compound of the present invention can be used as a material for an organic material layer of the organic light emitting device. In the case of manufacturing the organic light emitting device 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

Compound and organic light emitting device including the same

The present specification relates to a 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 the electrons and holes are transferred to different electrodes and used as a current source (voltage source). It is a type of light emitting device. 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 composed 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 When a voltage is applied between the two electrodes in the structure of the organic light emitting device, 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 It lights up when it falls back to the ground state. 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 material 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 required to realize a better natural color.

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 excellent luminous efficiency than the host constituting the light emitting layer is mixed in the light emitting layer in a small amount, 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, a material 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. is a stable and efficient material. The development of new materials continues to be supported by the

International Patent Publication No. 2017-126443

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

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

[Formula 1]

In Formula 1 above

When Ar11 and Ar12 are the same as or different from each other, and each independently represents -L-Ar2, Ar13 is hydrogen,

When Ar12 and Ar13 are the same as or different from each other, and each independently represents -L-Ar2, Ar11 is hydrogen,

L is a substituted or unsubstituted arylene group,

Ar2 is the following formula (2),

[Formula 2]

In Formula 2,

X is O, S, NR1 or Y1=Y2,

Y1 and Y2 are the same as or different from each other, each independently N or CR2,

R1 and R2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted a cyclic heteroaryl group,

Ar3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

In addition, according to an exemplary embodiment of the present invention, the 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 compound of the present invention can 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, and when the compound of the present invention is included in the electron transport layer of the organic light emitting device, high efficiency and It is possible to manufacture an organic light emitting device having a long lifespan.

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.

In Chemical Formula 1, -L-Ar2 is substituted in Nos. 1, 2, 2, and 3 of naphthalene to control the injection rate of electrons by maintaining an appropriate distance between molecules in forming a deposition film when manufacturing an organic light emitting device. When manufacturing a light emitting device, an organic light emitting device having high efficiency and lifespan can be manufactured.

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 the present 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 in which the substituent is substitutable, is 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; nitrile group (-CN); silyl group; boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine 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 heteroaryl 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 -SiY11Y12Y13, wherein Y11, Y12 and Y13 are each hydrogen; a 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, 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. 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 dimethyl boron group, a diethyl boron group, a t-butylmethyl boron group, a diphenyl boron group, a phenyl boron group, and the like.

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 alkyl group has 1 to 10 carbon atoms. 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, an octyl group, and the like.

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; There is an 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 be 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, but is not limited thereto.

In the present specification, the heteroaryl group is a cyclic group including at least one of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably from 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.

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

In the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently represents -L-Ar2.

In the present specification, Ar11 and Ar12 are the same as -L-Ar2.

In the present specification, Ar11 and Ar12 are different from each other and each independently represent -L-Ar2.

In the present specification, Ar12 and Ar13 are the same as or different from each other, and each independently represents -L-Ar2.

In the present specification, Ar12 and Ar13 are the same as -L-Ar2.

In the present specification, Ar12 and Ar13 are different from each other and each independently represent -L-Ar2.

In an exemplary embodiment of the present specification, X is O or S.

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

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

In an exemplary embodiment of the present specification, X is NR1.

In an exemplary embodiment of the present specification, X is Y1=Y2.

In an exemplary embodiment of the present specification, Y1=Y2 means that Y1 and Y2 are connected by a double bond.

In the exemplary embodiment of the present specification, when X is Y1=Y2, Chemical Formula 2 is represented by the following Chemical Formula 2-1.

[Formula 2-1]

In Formula 2-1, Ar3, Y1, and Y2 are defined as in Formula 2.

In an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

In an exemplary embodiment of the present specification, L is an arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L is an arylene group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, L is an arylene group having 6 to 15 carbon atoms.

In an exemplary embodiment of the present specification, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, a substituted or unsubstituted naphthalene group, a substituted or an unsubstituted divalent anthracene group, or a substituted or unsubstituted divalent phenanthrene group.

In an exemplary embodiment of the present specification, L is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted divalent biphenyl group.

In an exemplary embodiment of the present specification, L is a direct bond, a phenylene group, or a divalent biphenyl group, and the divalent biphenyl group is a divalent type in which a phenyl group is connected in series between the naphthalene core of Formula 1 and Ar2. It is a biphenyl group, or a divalent biphenyl group in a branched chain form.

The branched divalent biphenyl group refers to a form in which a phenylene group is present between the naphthalene core of Formula 1 and Ar2, and a phenyl group is substituted with the phenylene group.

In one embodiment of the present specification, L is a direct bond.

In an exemplary embodiment of the present specification, L is phenylene.

In the exemplary embodiment of the present specification, Y1 and Y2 are N.

In an exemplary embodiment of the present specification, Y1 and Y2 are CR2.

In an exemplary embodiment of the present specification, Y1 is N, and Y2 is CR2.

In the exemplary embodiment of the present specification, Y2 is N, and Y1 is CR2.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or an unsubstituted silyl group, or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted A silyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a silyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted hetero group having 3 to 30 carbon atoms It is an aryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted C 1 to C 10 alkyl group, a substituted or unsubstituted C 6 to C 30 aryl group, Or a substituted or unsubstituted C 3 to C 30 heteroaryl group.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted C1-C10 alkyl group, or an alkyl group-substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or aryl having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms group, or a heteroaryl group having 3 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or aryl having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms group, or a heteroaryl group having 3 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen, a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, carbon number A biphenyl group unsubstituted or substituted with an alkyl group of 1 to 10, a terphenyl group, a naphthyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a carbazole group, a triazine group, a pyrimidine group, a pyridine group, a dibenzofuran group, or a dibenzothiophene group.

In an exemplary embodiment of the present specification, R1 and R2 are hydrogen; or a phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R1 is hydrogen, a phenyl group, or a phenyl group substituted with a methyl group.

In an exemplary embodiment of the present specification, R2 is hydrogen.

In an exemplary embodiment of the specification, Ar3 is a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted C6-C20 aryl group, or a substituted or unsubstituted C3-C20 heteroaryl group.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted C6 to C15 aryl group, or a substituted or unsubstituted C3 to C15 heteroaryl group.

In an exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with CN, an alkyl group, an alkoxy group, or a heteroaryl group; or a C 3 to C 20 heteroaryl group unsubstituted or substituted with CN, an alkyl group, an alkoxy group, or a heteroaryl group.

In an exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with CN, an alkyl group, an alkoxy group, or a heteroaryl group; Or CN, or a C 3 to C 20 heteroaryl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a pyrimidine group, a pyridine group, a triazine group, a carbazole group, a thiophene group, a furan group, a dibenzofuran group, a dibenzothiophene group, a benzimidazole group, or a benzoxazole group;

The substituents are unsubstituted or substituted with any one or more selected from the group consisting of CN, an alkyl group, an alkoxy group, an aryl group, and a heteroaryl group.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a pyrimidine group, a pyridine group, a triazine group, a carbazole group, a thiophene group, a furan group, a dibenzofuran group, a dibenzothiophene group, a benzimidazole group, or a benzoxazole group;

The substituents are substituted or unsubstituted with any one or more selected from the group consisting of CN, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heteroaryl group having 3 to 20 carbon atoms. .

In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a pyrimidine group, a pyridine group, a triazine group, a carbazole group, a thiophene group, a furan group, a dibenzofuran group, a dibenzothiophene group, a benzimidazole group, or a benzoxazole group;

The substituents are selected from the group consisting of CN, a methyl group, an ethyl group, a propyl group, a terbutyl group, a methoxy group, an ethoxy group, a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, a dibenzothiophene group, and a carbazole group. It is substituted or unsubstituted by any one or more.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a pyrimidine group, a pyridine group, a triazine group, a carbazole group, a thiophene group, a furan group, a dibenzofuran group, a dibenzothiophene group, a benzimidazole group, or a benzoxazole group;

The substituents are CN, a methyl group, an ethyl group, a propyl group, a terbutyl group, a methoxy group, an ethoxy group, a dibenzofuran group, a dibenzothiophene group, and any one or more selected from the group consisting of a carbazole group substituted or unsubstituted do.

In the exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 15 carbon atoms, or a heteroaryl group having 3 to 15 carbon atoms.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a pyrimidine group, a pyridine group, a triazine group, a carbazole group, a thiophene group, a furan group, a dibenzofuran group, a dibenzothiophene group, a benzimidazole group, or a benzoxazole group.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyrimidine group, a pyridine group, a triazine group, a carbazole group, a thiophene group, a furan group, a dibenzofuran group, or a di a benzothiophene group,

The substituents are CN, a methyl group, an ethyl group, a propyl group, a terbutyl group, a methoxy group, an ethoxy group, a dibenzofuran group, a dibenzothiophene group, and any one or more selected from the group consisting of a carbazole group substituted or unsubstituted do.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group, a biphenyl group, a naphthyl group, a pyridine group, a carbazole group, a furan group, a dibenzofuran group, or a dibenzothiophene group,

The substituents are CN, a methyl group, an ethyl group, a propyl group, a terbutyl group, a methoxy group, an ethoxy group, a dibenzofuran group, a dibenzothiophene group, and any one or more selected from the group consisting of a carbazole group substituted or unsubstituted do.

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.

In addition, by introducing various substituents into the core structure of the structure as described above, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for the hole injection layer material, the hole transport material, the light emitting layer material, and the 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 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 the compound represented by Formula 1 above.

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

In another organic light emitting device, 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 It may further include a compound and lithium quinolate.

In an exemplary embodiment of the present specification, the layer for simultaneously injecting and transporting electrons includes the compound of Formula 1 and lithium quinolate in a weight ratio of 9:1 to 1:9.

In an exemplary embodiment of the present specification, the layer for simultaneously injecting and transporting electrons includes the compound of Formula 1 and lithium quinolate in a weight ratio of 6:4 to 4:6.

In an exemplary embodiment of the present specification, the layer for simultaneously injecting and transporting electrons includes the compound of Formula 1 and lithium quinolate in a weight ratio of 1:1.

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 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 the compound represented by Formula 1 above.

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 suppression 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 diode of the present invention may have the structure shown in FIG. 1 , but is not limited thereto.

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

1 illustrates a 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 such a structure, the compound represented by Formula 1 may be included in the organic material layer 3 .

2 shows a first electrode (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 and transport layer (9) on a substrate (1) and the structure of the organic light emitting device in which the second electrode 4 is stacked is exemplified. In such a structure, the compound represented by Formula 1 may be included in the electron injection and transport layer 9 .

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 transports and injects holes at the same time, a light emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously performs electron transport and electron injection. 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 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), and indium zinc oxide (IZO); 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. 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.

According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following Chemical Formula HT-1, but is not limited thereto.

[Formula HT-1]

In the formula HT-1,

At least one of X'1 to X'6 is N, the rest are CH,

R309 to R314 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted ring is formed by bonding with an adjacent group.

According to an exemplary embodiment of the present specification, X'1 to X'6 are N.

According to an exemplary embodiment of the present specification, R309 to R314 are nitrile groups.

According to an exemplary embodiment of the present specification, Formula HT-1 is represented by the following compound.

According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following Chemical Formula HT-2, but is not limited thereto.

[Formula HT-2]

In the formula HT-2,

R315 to R317 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of a combination thereof, or a substituted or unsubstituted ring by combining with an adjacent group,

r315 is an integer of 1 to 5, and when r315 is 2 or more, 2 or more of R315 are the same as or different from each other,

r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same as or different from each other.

According to an exemplary embodiment of the present specification, R317 is a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R317 is a carbazole group; phenyl group; biphenyl group; And any one selected from the group consisting of combinations thereof.

According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or combine with an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

According to an exemplary embodiment of the present specification, R315 and R316 are the same as or different from each other, and are each independently a phenyl group, or combine with an adjacent group to form an indene substituted with a methyl group.

According to an exemplary embodiment of the present specification, Chemical Formula HT-2 is represented by the following compound.

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 formed 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, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

According to an exemplary embodiment of the present specification, the host includes a compound represented by the following Chemical Formula H-1, but is not limited thereto.

[Formula H-1]

In Formula H-1,

L20 and L21 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar20 and Ar21 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R201 is hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r201 is an integer of 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.

In an exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently a direct bond; a phenylene group unsubstituted or substituted with deuterium; a biphenylrylene group unsubstituted or substituted with deuterium; a naphthylene group unsubstituted or substituted with deuterium; divalent dibenzofuran group; or a divalent dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4cyclic aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted C6-C20 monocyclic to 4-ring heterocyclic group.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with deuterium; a biphenyl group unsubstituted or substituted with deuterium; terphenyl group; a naphthyl group unsubstituted or substituted with deuterium; a thiophene group unsubstituted or substituted with a phenyl group; phenanthrene group; dibenzofuran group; naphthobenzofuran group; dibenzothiophene group; or a naphthobenzothiophene group.

In an exemplary embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, R201 is hydrogen.

According to an exemplary embodiment of the present specification, Formula H-1 is represented by the following compound.

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.

According to an exemplary embodiment of the present specification, the dopant includes a compound represented by the following Chemical Formula D-1, but is not limited thereto.

[Formula D-1]

In the formula D-1,

T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

t5 and t6 are each an integer of 1 to 4,

When t5 is 2 or more, the 2 or more T5 are the same as or different from each other,

When t6 is 2 or more, the 2 or more T6 are the same as or different from each other.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; a linear or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with a nitrile group or a linear or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, T1 to T6 are the same as or different from each other, and each independently hydrogen; isopropyl group; a phenyl group substituted with a nitrile group; or a phenyl group substituted with a methyl group.

According to an exemplary embodiment of the present specification, Formula D-1 is represented by the following compound.

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 well injecting electrons from the cathode and transferring them to the light emitting layer, 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 lowered, 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 increased 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.

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 electron 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 for illustrating 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 according to the appropriate selection of known starting materials by those skilled in the art for the type and number of substituents. As the reaction type and reaction conditions, those known in the art may be used.

[Scheme 1]

[Scheme 2]

In Schemes 1 and 2, Ar2, and L are as defined in Formula 1, Z is halogen or -SO ₃ C ₄ F ₉ , preferably Z is chloro, bromo, or -SO ₃ C ₄ It is F ₉ .

Suzuki coupling reactions in Schemes 1 and 2 are preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in Preparation Examples to be described later.

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.

Preparation Example 1-1: Preparation of compound E1

In a nitrogen atmosphere, E1-A (20 g, 69.9 mmol) and E1-B (48.8 g, 139.8 mmol) were placed in 400 ml of tetrahydrofuran, stirred and refluxed. After that, potassium carbonate (29 g, 209.8 mmol) was dissolved in 29 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (2.4 g, 2.1 mmol) was added. After the reaction for 3 hours, after cooling to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. this again in chloroform It was dissolved in 795 mL, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a white solid compound E1 (25.8 g, 65%, MS: [M+H] + = 569).

Preparation 1-2: Preparation of compound E2

Compound E2 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 589

Preparation Example 1-3: Preparation of compound E3

Compound E3 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 719

Preparation Example 1-4: Preparation of compound E4

Compound E4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 651

Preparation Example 1-5: Preparation of compound E5

In a nitrogen atmosphere, E5-A (20 g, 77.9 mmol) and E5-B (38.2 g, 77.9 mmol) were placed in 400 ml of Diox, stirred and refluxed. After that, potassium triphosphate (49.6 g, 233.7 mmol) was dissolved in 50 ml of water and thoroughly stirred, followed by dibenzylideneacetone palladium (1.3 g, 2.3 mmol) and tricyclohexylphosphine (1.3 g, 4.7 mmol). was put in. After the reaction for 5 hours, the resulting solid was filtered after cooling to room temperature. The solid was dissolved in 30 times 1367 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a yellow solid compound E5 (28.2 g, 62%, MS: [M+H] + =585).

Preparation Example 1-6: Preparation of compound E6

Compound E6 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 743

Preparation Example 1-7: Preparation of compound E7

Compound E7 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 719

Preparation Example 1-8: Preparation of compound E8

Compound E8 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 721

Preparation Example 1-9: Preparation of compound E9

Compound E9 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 669

Preparation Example 1-10: Preparation of compound E10

Compound E10 was prepared in the same manner as in Preparation Example 1-5, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 643

Preparation Example 1-11: Preparation of compound E11

Compound E11 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 693

Preparation Example 1-12: Preparation of compound E12

Compound E12 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 703

Preparation Example 1-13: Preparation of compound E13

Compound E13 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 721

Preparation Example 1-14: Preparation of compound E14

Compound E14 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 669

Preparation Example 1-15: Preparation of compound E15

Compound E15 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared as in the above reaction scheme.

MS: [M+H] ⁺ = 569

Preparation Example 1-16: Preparation of compound E16

Compound E16 was prepared in the same manner as in Preparation Example 1-5, except that each starting material was prepared as in the above reaction scheme.

[Example]

Example 1-1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 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 ITO for 30 minutes, ultrasonic cleaning 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. A first hole transport layer and a second hole transport layer were formed by sequentially vacuum-depositing 50 Å of the HAT compound and 60 Å of the HT-A compound on the hole injection layer.

Then, the following BH compound and BD compound were vacuum-deposited at a weight ratio of 25:1 to a thickness of 200 Å on the second hole transport layer to form a light emitting layer.

On the light emitting layer, the compound E1 prepared above and the compound LiQ below were vacuum-deposited at a weight ratio of 1:1 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 1000 Å on the electron injection and transport layer.

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

Examples 1-2 to 1-16

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that compounds E2 to E16 of Table 1 were used instead of compound E1 of Example 1-1.

Comparative Examples 1-1 to 1-14

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that compounds ET-1 to ET-14 in Table 1 below were used instead of Compound E1 of Example 1-1. The compounds ET-1 to ET-14 are as follows.

[Experimental example]

Experimental Example 1

For the organic light emitting diodes prepared in Examples 1-1 to 1-16 and Comparative Examples 1-1 to 1-14, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² , and 20 mA/cm At a current density of ² , the time (T90) to be 90% of the initial luminance was measured. The results are shown in Table 1 below.

division compound Voltage (V)
(@10mA/
cm ² ) Efficiency (cd/A)
(@10mA/cm ² ) Color coordinates (x, y) Lifetime (hr)
(T90 at 20 mA/cm ² ) Example 1-1 E1 3.98 5.01 (0.140, 0.089) 172 Example 1-2 E2 3.90 5.16 (0.140, 0.090) 169 Examples 1-3 E3 3.94 5.06 (0.140, 0.089) 158 Examples 1-4 E4 4.14 4.86 (0.141, 0.089) 229 Examples 1-5 E5 3.90 5.11 (0.140, 0.090) 163 Examples 1-6 E6 4.02 5.21 (0.140, 0.089) 150 Examples 1-7 E7 4.14 4.60 (0.140, 0.090) 157 Examples 1-8 E8 4.06 4.91 (0.140, 0.089) 177 Examples 1-9 E9 4.07 4.86 (0.141, 0.089) 181 Examples 1-10 E10 4.10 4.65 (0.140, 0.090) 160 Examples 1-11 E11 4.22 4.74 (0.140, 0.089) 153 Examples 1-12 E12 4.18 4.79 (0.140, 0.090) 153 Examples 1-13 E13 4.02 4.96 (0.140, 0.089) 175 Examples 1-14 E14 4.07 4.91 (0.141, 0.089) 177 Examples 1-15 E15 4.04 4.98 (0.140, 0.089) 173 Examples 1-16 E16 4.20 4.78 (0.141, 0.089) 162 Comparative Example 1-1 ET-1 4.46 2.20 (0.140, 0.090) 40 Comparative Example 1-2 ET-2 4.52 1.96 (0.140, 0.089) 118 Comparative Example 1-3 ET-3 4.57 1.92 (0.140, 0.090) 111 Comparative Example 1-4 ET-4 4.80 1.85 (0.140, 0.089) 160 Comparative Example 1-5 ET-5 4.52 1.94 (0.141, 0.089) 114 Comparative Example 1-6 ET-6 4.66 1.98 (0.140, 0.090) 105 Comparative Example 1-7 ET-7 4.80 1.75 (0.140, 0.089) 110 Comparative Examples 1-8 ET-8 4.71 1.96 (0.140, 0.090) 124 Comparative Example 1-9 ET-9 4.72 1.99 (0.140, 0.089) 126 Comparative Example 1-10 ET-10 4.75 1.77 (0.141, 0.089) 112 Comparative Example 1-11 ET-11 4.72 2.09 (0.140, 0.090) 35 Comparative Example 1-12 ET-12 4.85 1.82 (0.140, 0.089) 107 Comparative Example 1-13 ET-13 4.66 1.98 (0.140, 0.090) 123 Comparative Example 1-14 ET-14 4.72 2.01 (0.140, 0.089) 124

As shown in Table 1, the compound represented by Formula 1 according to the present specification may be used in an organic material layer capable of simultaneously performing electron injection and electron transport of the organic light emitting device. Comparing Examples 1-1 to 1-16 of Table 1 and Comparative Examples 1-1 and 1-11, the organic light emitting device including the compound of Formula 1 according to the present specification includes a compound in which Ar ₁ is phenyl. It was confirmed that the organic light emitting device showed significantly superior characteristics in terms of efficiency and lifespan.

Comparing Examples 1-1 to 1-16 of Table 1 and Comparative Examples 1-2 to 1-7 and 1-12, the organic light emitting device including the compound of Formula 1 according to the present specification is -L to naphthalene -Ar2 has significantly superior properties in terms of efficiency than organic light emitting devices including compounds substituted at 1,4, 1,7, 1,5, 2,7, 2,6, 1,6 visibility could be confirmed.

Comparing Examples 1-1 to 1-16 of Table 1 and Comparative Examples 1-10, the organic light emitting device including the compound of Formula 1 according to the present specification is superior to the organic light emitting device including the compound in which Ar1 is anthracene. It was confirmed that the characteristics were remarkably excellent in terms of efficiency.

Comparing Examples 1-1 to 1-16 of Table 1 with Comparative Examples 1-8, 1-9, 1-13, and 1-14, an organic light-emitting device including the compound of Formula 1 according to the present specification was confirmed to show significantly superior properties in terms of efficiency than organic light emitting devices including a compound in which L is a direct bond.

This is because when an organic light emitting device is manufactured using a compound substituted at 1, 2, 2, and 3 of naphthalene and L is an unsubstituted aryl group, the electron injection rate is controlled by maintaining an appropriate distance between molecules in forming a deposition film. seems to be

1: substrate
2: first electrode
3: organic layer
4: second electrode
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 (12)

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

In Formula 1 above
When Ar11 and Ar12 are the same as or different from each other, and each independently represents -L-Ar2, Ar13 is hydrogen,
When Ar12 and Ar13 are the same as or different from each other, and each independently represents -L-Ar2, Ar11 is hydrogen,
L is a substituted or unsubstituted arylene group,
Ar2 is the following formula (2),
[Formula 2]

In Formula 2,
X is O, S, NR1 or Y1=Y2,
Y1 and Y2 are the same as or different from each other, each independently N or CR2,
R1 and R2 are the same as or different from each other, and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted a cyclic heteroaryl group,
Ar3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. The compound of claim 1, wherein Ar11 and Ar12 are the same as or different from each other, and each independently represents -L-Ar2. The compound of claim 1, wherein Ar12 and Ar13 are the same as or different from each other, and each independently represents -L-Ar2. The compound of claim 1, wherein X is Y1=Y2. The compound of claim 1, wherein X is O or S. The compound of claim 1, wherein L is a phenylene group. The compound according to claim 1, wherein 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 of the organic material layers comprises the compound according to any one of claims 1 to 7 . The organic light-emitting device of claim 8 , wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound. The organic light emitting diode of claim 8, wherein the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound. The organic light-emitting device of claim 8 , wherein 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, the electron injection layer, or the electron injection and transport layer includes the compound. The organic light emitting diode of claim 8 , wherein the organic material layer includes an emission layer, and the emission layer includes the compound.

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