Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2024-0031728 filed in the Korean Intellectual Property Office on March 6, 2024, the entire contents of which are incorporated into this specification.

[0002] The present invention relates to a compound and an organic light-emitting device comprising the same. Background Art

[0003] In this specification, an organic light-emitting device is a light-emitting device that uses an organic semiconductor material and requires the exchange of holes and / or electrons between an electrode and the organic semiconductor material. Organic light-emitting devices can be roughly divided into the following two types according to their working principles. The first type is a light-emitting device that uses photons flowing into the device from an external light source to form excitons in the organic layer. The excitons are separated into electrons and holes, and the electrons and holes are respectively transferred to different electrodes to be used as a current source (voltage source). The second type is a light-emitting device that applies voltage or current to two or more electrodes, thereby injecting holes and / or electrons into the organic semiconductor material layer that forms an interface with the electrodes, and works through the injected electrons and holes.

[0004] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light-emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by 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. For the structure of such an organic light-emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons transition back to the ground state, light is emitted. Such 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.

[0005] In order to fully utilize the excellent characteristics of the above-mentioned organic light-emitting devices, the substances that constitute the organic layer in the device, such as hole injection substances, hole transport substances, luminescent substances, electron suppression substances, electron transport substances, electron injection substances, etc., are backed by stable and effective materials, and therefore there is a continuous demand for the development of new materials.

[0006] Prior art literature

[0007] Patent Literature

[0008] (Patent Document 1) International Patent Publication No. 2017-126443 Summary of the Invention

[0009] Technical issues

[0010] This specification describes a compound and an organic light-emitting device including the same.

[0011] Solution to the problem

[0012] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In the above Chemical Formula 1,

[0016] At least one of X1 to X3 is N, and the rest are CR,

[0017] At least one of X4 to X6 is N, and the rest are CR.

[0018] R is hydrogen, deuterium, nitrile, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amino, or substituted or unsubstituted heteroaryl,

[0019] At least one of R1 to R3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and the others are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted heteroaryl group,

[0020] Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,

[0021] a to c are each an integer from 1 to 4,

[0022] When a is 2 or more, R1 are the same or different.

[0023] When b is 2 or more, R2 are the same or different.

[0024] When c is 2 or more, R3 are the same as or different from each other.

[0025] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided, which includes: a first electrode, a second electrode arranged opposite to the above-mentioned first electrode, and one or more organic layers arranged between the above-mentioned first electrode and the above-mentioned second electrode, and one or more of the above-mentioned organic layers contain the above-mentioned compound.

[0026] Effects of the Invention

[0027] The compounds of the present invention can be used as materials for the organic layer of an organic light-emitting device, thereby achieving improved efficiency, lower driving voltage, and / or improved lifespan characteristics in the organic light-emitting device. In particular, the compound represented by the above-mentioned Chemical Formula 1 can be used as an electron transport or electron injection material. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 and 2 An example of the organic light-emitting device according to the present invention is illustrated.

[0029] Explanation of symbols

[0030] 1: Substrate

[0031] 2: First electrode

[0032] 3: Organic layer

[0033] 4: Second electrode

[0034] 5: Hole injection layer

[0035] 6: Hole transport layer

[0036] 7: Luminous layer

[0037] 8: Electron injection and transport layer DETAILED DESCRIPTION

[0038] Next, this specification is described in more detail.

[0039] In this specification, when it is stated that a certain part “includes / comprising” a certain component, unless otherwise stated, it means that other components may be further included, rather than excluding other components.

[0040] In this specification, when it is stated that a certain component is located “on” another component, it includes not only a case where the certain component is in contact with the other component, but also a case where other components are present between the two components.

[0041] The term "substituted" as used above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent. The position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are two or more substitutions, the two or more substituents may be the same or different from each other.

[0042] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a silyl group, a boron group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or substituted with a substituent consisting of two or more of the above-mentioned substituents linked together, or having no substituents. For example, a "substituent consisting of two or more substituents linked together" can be a biphenyl group. That is, a biphenyl group can be an aryl group, or it can be interpreted as a substituent consisting of two phenyl groups linked together.

[0043] Examples of the above-mentioned substituents are described below, but are not limited thereto.

[0044] In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

[0045] In this specification, a silyl group can be represented by the chemical formula -SiY1Y2Y3, where Y1, Y2, and Y3 can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl.

[0046] In this specification, a boryl group can be represented by the chemical formula -BY4Y5, where Y4 and Y5 can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boryl group include, but are not limited to, dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, and phenylboryl.

[0047] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, and octyl.

[0048] In this specification, the arylalkyl group refers to an alkyl group substituted with an aryl group. The number of carbon atoms is not particularly limited, but according to one embodiment, the alkyl group has 1 to 30 carbon atoms, and the aryl group substituted in the alkyl group has 6 to 30 carbon atoms.

[0049] In the present specification, the amino group can be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methylanthrylamino, diphenylamino, dimethyltolylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterbiphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino. The present invention is not limited to these.

[0050] In the present specification, an N-alkylarylamine group refers to an amine group in which an alkyl group and an aryl group are substituted on the nitrogen of the amine group.

[0051] In the present specification, an N-arylheteroarylamine group refers to an amine group in which an aryl group or a heteroaryl group is substituted on the nitrogen of the amine group.

[0052] In the present specification, an N-alkylheteroarylamine group refers to an amine group in which the nitrogen of the amine group is substituted with an alkyl group and a heteroaryl group.

[0053] In this specification, alkylamino, N-arylalkylamino, alkylthio Alkylsulfonyl The alkyl group in the N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specifically, examples of the alkylthio group include methylthio, ethylthio, tert-butylthio, hexylthio, and octylthio, and examples of the alkylsulfonyl group include methylsulfonyl, ethylsulfonyl, propylsulfonyl, and butylsulfonyl, but are not limited thereto.

[0054] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups.

[0055] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenylene, yl, fluorenyl, etc., but are not limited thereto.

[0056] In the present specification, a heteroaryl group is a cyclic group containing one or more heteroatoms selected from N, O, P, S, Si, and Se. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. Examples of heterocyclic groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, and carbazolyl.

[0057] In this specification, unless otherwise defined, all technical terms and scientific terms used in this specification have the same meaning as those generally understood by those skilled in the art. Methods and materials similar to or equivalent to the description in this specification can be used for the implementation or test of embodiments of the present invention, but suitable methods and materials are described later. All publications, patent applications, patents and other references mentioned in this specification are included in this specification as a whole as a reference. In the case of conflict, if no specific passage is mentioned, the present specification including the definition takes precedence. In addition, materials, methods and embodiments are illustrative and not intended to be limiting.

[0058] In the present specification, at least one of the above R1 to R3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted heteroaryl group.

[0059] In the present specification, at least one of the above R1 to R3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted heteroaryl group.

[0060] In the present specification, at least one of the above R1 to R3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted heteroaryl group.

[0061] In the present specification, at least one of the above R1 to R3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted amino group, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0062] In the present specification, at least one of the above R1 to R3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0063] In the present specification, at least one of the above R1 to R3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted triazinyl group, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a methyl group, an ethyl group, a tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted triazinyl group.

[0064] In the present specification, at least one of the above R1 to R3 is a phenyl group which may be substituted by a nitrile group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthroline group, a pyridyl group which may be substituted by an aryl group having 6 to 30 carbon atoms, or a triazine group which may be substituted by an aryl group having 6 to 30 carbon atoms, and the rest are the same or different and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group which may be substituted by a nitrile group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthroline group, a pyridyl group which may be substituted by an aryl group having 6 to 30 carbon atoms, or a triazine group which may be substituted by an aryl group having 6 to 30 carbon atoms.

[0065] In the present specification, one of the above R1 to R3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and the others are the same as or different from each other and are independently hydrogen, deuterium or nitrile.

[0066] In the present specification, two of the above R1 to R3 are the same as or different from each other, and are independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and the rest are hydrogen, deuterium or nitrile groups.

[0067] In the present specification, one of the above R1 to R3 is an unsubstituted aryl group, and the others are the same as or different from each other and are independently hydrogen, deuterium or nitrile.

[0068] In the present specification, two of the above R1 to R3 are the same as or different from each other and are independently an unsubstituted aryl group, and the rest are hydrogen, deuterium or nitrile groups.

[0069] In the present specification, one of the above R1 to R3 is a substituted or unsubstituted aryl group, and the others are the same as or different from each other and are independently hydrogen, deuterium or nitrile.

[0070] In the present specification, two of the above R1 to R3 are the same as or different from each other, and are independently a substituted or unsubstituted aryl group, and the rest are hydrogen, deuterium or nitrile groups.

[0071] In the present specification, one of the above R1 to R3 is a substituted or unsubstituted heteroaryl group, and the others are the same as or different from each other and are independently hydrogen, deuterium or nitrile.

[0072] In the present specification, two of the above R1 to R3 are the same as or different from each other, and are independently a substituted or unsubstituted heteroaryl group, and the rest are hydrogen, deuterium or nitrile groups.

[0073] In the present specification, one of the above R1 to R3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted triazinyl group, and the rest are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a methyl group, an ethyl group, a tert-butyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted triazinyl group.

[0074] In the present specification, one of the above R1 to R3 is a phenyl group which may be substituted by a nitrile group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrolinyl group, a pyridyl group which may be substituted by an aryl group having 6 to 30 carbon atoms, or a triazinyl group which may be substituted by an aryl group having 6 to 30 carbon atoms, and the rest are the same or different and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a methyl group, an ethyl group, a tert-butyl group, a phenyl group which may be substituted by a nitrile group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthrolinyl group, a pyridyl group which may be substituted by an aryl group having 6 to 30 carbon atoms, or a triazinyl group which may be substituted by an aryl group having 6 to 30 carbon atoms.

[0075] In the present specification, two of the above R1 to R3 are substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted pyridyl, or substituted or unsubstituted triazinyl, and the rest are hydrogen, deuterium, nitrile, halogen, methyl, ethyl, tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthroline, substituted or unsubstituted pyridyl, or substituted or unsubstituted triazinyl.

[0076] In the present specification, two of the above R1 to R3 are phenyl which may be substituted by a nitrile group, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthroline, pyridyl which may be substituted by an aryl group having 6 to 30 carbon atoms, or triazinyl which may be substituted by an aryl group having 6 to 30 carbon atoms, and the rest are hydrogen, deuterium, a nitrile group, a halogen group, a methyl group, an ethyl group, a tert-butyl group, phenyl which may be substituted by a nitrile group, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenanthroline, pyridyl which may be substituted by an aryl group having 6 to 30 carbon atoms, or triazinyl which may be substituted by an aryl group having 6 to 30 carbon atoms.

[0077] In this specification, the above-mentioned Ar1 and Ar2 are identical to each other.

[0078] In this specification, the above-mentioned Ar1 and Ar2 are different from each other.

[0079] In this specification, the above-mentioned Ar3 and Ar4 are identical to each other.

[0080] In this specification, the above-mentioned Ar3 and Ar4 are different from each other.

[0081] In this specification, the above-mentioned Ar1 to Ar4 are the same as one another.

[0082] In this specification, the above-mentioned Ar1 to Ar4 are different from each other.

[0083] In the present specification, Ar1 to Ar4 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.

[0084] In the present specification, Ar1 to Ar4 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.

[0085] In the present specification, the above-mentioned Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0086] In the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, or a triphenylene group.

[0087] In the present specification, the above-mentioned Ar1 to Ar4 are phenyl groups.

[0088] In the present specification, at least one of Ar1 to Ar4 is an aryl group having 10 to 30 carbon atoms, and the others are the same as or different from each other and are independently substituted or unsubstituted aryl groups.

[0089] In the present specification, at least one of Ar1 to Ar4 is an aryl group having 10 to 30 carbon atoms, and the others 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.

[0090] In the present specification, at least one of Ar1 to Ar4 is an aryl group having 10 to 25 carbon atoms, and the others are the same as or different from each other and are independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0091] In the present specification, at least one of Ar1 to Ar4 is an aryl group having 10 to 20 carbon atoms, and the others are the same as or different from each other and are each independently a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.

[0092] In the present specification, one of the above-mentioned Ar1 to Ar4 is an aryl group having 10 to 30 carbon atoms, and the others are the same as or different from each other and are independently substituted or unsubstituted aryl groups.

[0093] In the present specification, one of Ar1 to Ar4 is an aryl group having 10 to 25 carbon atoms, and the others are the same as or different from each other and are independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0094] In the present specification, one of the above Ar1 to Ar4 is a naphthyl, biphenyl, anthracenyl, phenanthrenyl or triphenylene, and the rest are the same as or different from each other and are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, or a substituted or unsubstituted triphenylene.

[0095] In the present specification, one of the above-mentioned Ar1 to Ar4 is naphthyl, biphenyl, anthracenyl, phenanthrenyl or triphenylene, and the rest are the same as or different from each other and are each independently a deuterium-substituted or unsubstituted phenyl, a deuterium-substituted or unsubstituted naphthyl, a deuterium-substituted or unsubstituted anthracenyl, a deuterium-substituted or unsubstituted phenanthrenyl, or a deuterium-substituted or unsubstituted triphenylene.

[0096] In the present specification, one of the above Ar1 to Ar4 is naphthyl, biphenyl, anthracenyl, phenanthryl or triphenylene, and the others are the same as or different from each other and are independently phenyl, naphthyl, anthracenyl, phenanthryl or triphenylene.

[0097] In the present specification, two of the above Ar1 to Ar4 are the same as or different from each other and are each independently an aryl group having 10 to 30 carbon atoms, and the remaining two are the same as or different from each other and are each independently a substituted or unsubstituted aryl group.

[0098] In the present specification, two of the above Ar1 to Ar4 are the same or different and are each independently an aryl group having 10 to 30 carbon atoms, and the remaining are the same or different and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0099] In the present specification, one of Ar1 and Ar2 is an aryl group having 10 to 30 carbon atoms, and the others are substituted or unsubstituted aryl groups.

[0100] In the present specification, one of Ar1 and Ar2 is an aryl group having 10 to 30 carbon atoms, and the others are the same as or different from each other and are independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0101] In the present specification, one of the above-mentioned Ar1 and Ar2 is naphthyl, anthracenyl, phenanthrenyl or triphenylene, and the rest are substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted triphenylene.

[0102] In the present specification, one of the above-mentioned Ar1 and Ar2 is naphthyl, anthracenyl, phenanthrenyl or triphenylene, and the others are deuterium-substituted or unsubstituted phenyl, deuterium-substituted or unsubstituted naphthyl, deuterium-substituted or unsubstituted anthracenyl, deuterium-substituted or unsubstituted phenanthrenyl, or deuterium-substituted or unsubstituted triphenylene.

[0103] In the present specification, one of Ar1 and Ar2 is naphthyl, anthracenyl, phenanthryl or triphenylene, and the others are phenyl, naphthyl, anthracenyl, phenanthryl or triphenylene.

[0104] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 10 to 30 carbon atoms.

[0105] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 10 to 25 carbon atoms.

[0106] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0107] In the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a naphthyl group, anthracenyl group, phenanthrenyl group or triphenylene group.

[0108] In the present specification, one of Ar3 and Ar4 is an aryl group having 10 to 30 carbon atoms, and the others are substituted or unsubstituted aryl groups.

[0109] In the present specification, one of Ar3 and Ar4 is an aryl group having 10 to 30 carbon atoms, and the others are the same as or different from each other and are independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.

[0110] In the present specification, one of the above-mentioned Ar3 and Ar4 is naphthyl, anthracenyl, phenanthrenyl or triphenylene, and the rest are substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted triphenylene.

[0111] In the present specification, one of Ar3 and Ar4 is naphthyl, anthracenyl, phenanthryl or triphenylene, and the others are phenyl, naphthyl, anthracenyl, phenanthryl or triphenylene.

[0112] In the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently an aryl group having 10 to 30 carbon atoms.

[0113] In the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently an aryl group having 10 to 25 carbon atoms.

[0114] In the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a naphthyl group, anthracenyl group, phenanthrenyl group or triphenylene group.

[0115] In this specification, X1 to X3 are N.

[0116] In the present specification, any two of the above X1 to X3 are N, and the remaining one is CH. In the present specification, any two of the above X1 to X3 are N, and the remaining one is CH.

[0117] In the present specification, X1 among the above X1 to X3 is N, and the rest are CH.

[0118] In the present specification, X2 among the above X1 to X3 is N, and the rest are CH.

[0119] In the present specification, X3 among the above X1 to X3 is N, and the rest are CH.

[0120] In this specification, X1 and X2 are N, and X3 is CH.

[0121] In this specification, X1 and X3 are N, and X2 is CH.

[0122] In this specification, X2 and X3 are N, and X1 is CH.

[0123] In this specification, the above Chemical Formula 1 is any one of the following compounds.

[0124]

[0125]

[0126] The substituents of the compound of Chemical Formula 1 can be combined by methods known in the art, and the type, position or number of the substituents can be changed according to techniques known in the art.

[0127] Furthermore, by introducing various substituents into the core structure of the aforementioned structure, compounds with the inherent properties of the introduced substituents can be synthesized. For example, by introducing substituents primarily 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 aforementioned core structure, it is possible to synthesize materials that meet the requirements of each organic layer.

[0128] In addition, the organic light-emitting device according to the present invention is characterized in that it includes: a first electrode, a second electrode arranged opposite to the above-mentioned first electrode, and one or more organic layers arranged between the above-mentioned first electrode and the above-mentioned second electrode, and one or more of the above-mentioned organic layers contains the above-mentioned compound.

[0129] The organic light-emitting device of the present invention uses the above-mentioned compound to form one or more organic layers, and can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0130] When manufacturing organic light-emitting devices, the above-mentioned compounds can be formed into organic layers not only by vacuum evaporation but also by solution coating. Solution coating methods include, but are not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roller coating.

[0131] The organic layer of the organic light-emitting device of the present invention may be a single-layer structure or a multilayer structure comprising two or more organic layers. For example, the organic light-emitting device of the present invention may include 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, and the like as organic layers. However, the structure of the organic light-emitting device is not limited to this, and may include a fewer number of organic layers or a greater number of organic layers.

[0132] In the organic light-emitting device of the present invention, the organic layer may include one or more layers of an electron transport layer and an electron injection and transport layer, and one or more layers of the layers may contain the compound represented by Chemical Formula 1.

[0133] In the organic light-emitting device of the present invention, the electron injection and transport layer may contain both a metal complex and the compound of the present specification. In this case, a lithium complex or the like may be used as the metal complex.

[0134] In another organic light-emitting device, the organic 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 Chemical Formula 1.

[0135] In the organic light-emitting device of the present invention, the organic layer may include one or more layers of a hole injection layer, a hole transport layer, and a layer that simultaneously performs hole injection and hole transport, and one or more of the layers may contain the compound represented by the above Chemical Formula 1.

[0136] In another organic light-emitting device, the organic 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 Chemical Formula 1.

[0137] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0138] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0139] (1) Anode / HTL / Emitting Layer / Cathode

[0140] (2) Anode / HOL injection layer / HOL transport layer / Emitting layer / Cathode

[0141] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0142] (4) Anode / HTL / Luminescent Layer / Electron Transport Layer / Cathode

[0143] (5) Anode / HTL / Luminescent Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0144] (6) Anode / HOL injection layer / HOL transport layer / Luminescent layer / Electron transport layer / Cathode

[0145] (7) Anode / Hole Injection Layer / Hole Transport Layer / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0146] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0147] (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0148] (10) Anode / HTL / Electron Suppression Layer / Emitting Layer / Electron Transport Layer / Cathode

[0149] (11) Anode / HTL / Electron Suppression Layer / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0150] (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Suppression Layer / Emitting Layer / Electron Transport Layer / Cathode

[0151] (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Suppression Layer / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0152] (14) Anode / Hole Transport Layer / Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Cathode

[0153] (15) Anode / Hole Transport Layer / Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0154] (16) Anode / Hole Injection Layer / Hole Transport Layer / Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Cathode

[0155] (17) Anode / Hole Injection Layer / Hole Transport Layer / Emitting Layer / Hole Suppression Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0156] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0157] The structure of the organic light emitting device of the present invention may have the following Figure 1 and Figure 2 The structure shown is not limited thereto.

[0158] Figure 1 exemplifies the structure of an organic light-emitting device in which a first electrode 2, an organic layer 3, and a second electrode 4 are sequentially stacked on a substrate 1. In the above structure, the compound represented by Chemical Formula 1 may be contained in the organic layer 3.

[0159] Figure 2 exemplifies the structure of an organic light-emitting device in which 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 stacked on a substrate 1. In the above structure, the compound represented by Chemical Formula 1 may be contained in the electron injection and transport layer 8.

[0160] For example, an organic light-emitting device according to the present invention can be manufactured by depositing a metal, a conductive metal oxide, or an alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode. Furthermore, one or more organic layers selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons are formed on the anode. Finally, a material that can function as a cathode is deposited on the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0161] The organic 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 also have a single-layer structure. Furthermore, the organic layer may be fabricated into a smaller number of layers using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, doctor blade coating, screen printing, inkjet printing, or thermal transfer.

[0162] The anode is an electrode for injecting holes. Anode materials are generally preferred to have a large work function in order to facilitate the smooth injection of holes 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); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0163] The cathode is an electrode that injects electrons. Generally, cathode materials with a low work function are preferred to facilitate electron injection into the organic layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0164] The hole injection layer is a layer that plays a role in smoothly injecting holes from the anode to the light-emitting layer. The hole injection material is a material that can well receive holes from the anode at low voltage. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material 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 organic matter, hexanitrile hexaazatriphenylene organic matter, quinacridone organic matter, perylene organic matter, anthraquinone and polyaniline and polythiophene conductive polymers, but are not limited thereto. The thickness of the hole injection layer can be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing the hole injection characteristics from being reduced. When it is 150 nm or less, it has the advantage of preventing the driving voltage from rising when the thickness of the hole injection layer is too thick to improve the migration of holes.

[0165] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0166] [Chemical formula HI-1]

[0167]

[0168] In the above chemical formula HI-1,

[0169] R403 to R406 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0170] L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0171] l403 is an integer from 1 to 3. When l403 is 2 or greater, L403 are the same as or different from each other.

[0172] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are independently any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0173] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms substituted with an aryl group having 6 to 30 carbon atoms.

[0174] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, or a carbazolyl group substituted with a phenyl group.

[0175] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently a phenyl group or a carbazolyl group substituted with a phenyl group.

[0176] According to one embodiment of the present specification, L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.

[0177] According to one embodiment of the present specification, L403 is a phenylene group, a divalent biphenyl group, or a divalent carbazolyl group which may be substituted with an aryl group.

[0178] According to one embodiment of the present specification, L403 is spiroacridine-9,9'-fluorene substituted with a phenyl group.

[0179] According to one embodiment of the present specification, the chemical formula HI-1 is selected from the following compounds.

[0180]

[0181] The hole transport layer facilitates hole transport. Hole transport materials are substances that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer. Suitable materials have high hole mobility. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0182] According to one 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.

[0183] [Chemical formula HT-1]

[0184]

[0185] In the above chemical formula HT-1,

[0186] At least one of X'1 to X'6 is N, and the others are CH,

[0187] R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0188] According to one embodiment of the present specification, X'1 to X'6 are N.

[0189] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0190] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0191]

[0192] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0193] [Chemical formula HT-2]

[0194]

[0195] In the above chemical formula HT-2,

[0196] R400 to R402 are the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0197] L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0198] According to one embodiment of the present specification, R400 to R402 are the same as or different from each other, and are independently any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0199] According to one embodiment of the present specification, the above-mentioned L402 is a phenylene group.

[0200] According to one embodiment of the present specification, R402 is a carbazolyl group substituted with a phenyl group.

[0201] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and are independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0202] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and are each independently an aryl group which may be substituted or unsubstituted by an alkyl group.

[0203] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and are each independently a phenyl group or a spirobifluorenyl group.

[0204] According to one embodiment of the present specification, the chemical formula HT-2 is selected from the following compounds.

[0205]

[0206] A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

[0207] An electron suppression layer may be provided between the hole transport layer and the light emitting layer. The electron suppression layer may be made of the aforementioned spiro compound or a material known in the art.

[0208] The light-emitting layer can emit red, green or blue light and can be formed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but not limited thereto.

[0209] The host material of the light-emitting layer includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited thereto.

[0210] According to one embodiment of the present specification, the host includes a compound represented by the following chemical formula H-1, but is not limited thereto.

[0211] [Chemical formula H-1]

[0212]

[0213] In the above chemical formula H-1,

[0214] L20 and L21 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0215] Ar20 and Ar21 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0216] R201 is hydrogen, deuterium, a 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,

[0217] r201 is an integer of 1 to 8. When r201 is 2 or more, two or more R201s are the same as or different from each other.

[0218] In one embodiment of the present specification, L20 and L21 are the same as or different from each other and are 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.

[0219] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and are each independently a direct bond, a deuterium-substituted or unsubstituted phenylene group, a deuterium-substituted or unsubstituted biphenylene group, a deuterium-substituted or unsubstituted naphthylene group, a divalent dibenzofuranyl group, or a divalent dibenzothiophenyl group.

[0220] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0221] In one embodiment of the present specification, Ar20 and Ar21 are the same or different and are 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.

[0222] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0223] In one embodiment of the present specification, Ar20 and Ar21 are the same or different from each other and are each independently substituted or unsubstituted phenyl by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; biphenyl by deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthyl by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; substituted or unsubstituted thienyl group with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; dibenzothienyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or naphthobenzothienyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0224] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a terphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a phenyl-substituted or unsubstituted thienyl group, a phenanthrenyl group, a dibenzofuranyl group, a naphthiobenzofuranyl group, a dibenzothiophenyl group or a naphthiobenzothiophenyl group.

[0225] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently 1-naphthyl or 2-naphthyl.

[0226] According to one embodiment of the present specification, R201 is a phenyl group.

[0227] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0228]

[0229] When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent substances such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum, tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy)3 (facial tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as the light-emitting dopant, but are not limited to these. When the light-emitting layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers can be used as the light-emitting dopant, but are not limited to these.

[0230] According to one embodiment of the present specification, the dopant includes a compound represented by the following Chemical Formula D-1, but is not limited thereto.

[0231] [Chemical Formula D-1]

[0232]

[0233] In the above chemical formula D-1,

[0234] T1 to T6 are the same as or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0235] t5 and t6 are each an integer from 1 to 4,

[0236] When the above t5 is 2 or more, the above two or more T5 are the same or different from each other.

[0237] When the above-mentioned t6 is 2 or more, the above-mentioned two or more T6 are the same as or different from each other.

[0238] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other and are each independently hydrogen, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, 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.

[0239] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other and are independently hydrogen; a straight-chain 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 by a nitrile group or a straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms that is unsubstituted or substituted by a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0240] According to one embodiment of the present specification, T1 to T6 are the same as or different from each other, and are each independently hydrogen, a phenyl group, or a terphenyl group substituted with a trimethylsilyl group or a methyl group.

[0241] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0242]

[0243] A hole suppression layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

[0244] The above-mentioned electron transport layer can play a role in making the transmission of electrons smooth. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a material with a large electron mobility is suitable. As a specific example, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. The thickness of the electron transport layer can be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, it has the advantage of preventing the electron transport characteristics from being reduced. When it is 50 nm or less, it has the advantage of preventing the driving voltage from rising in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.

[0245] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have excellent electron injection effects on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0246] The electron injection and transport layer is a layer that simultaneously injects and transports electrons, and the materials for the electron injection and transport layers described above can be used. In addition, when using the organic light-emitting device of the present specification, the electron injection and transport layer can contain both a metal coordination compound and the compound of the present specification.

[0247] Examples of the metal coordination compounds include, but are not limited to, 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)gallium chloride, bis(2-methyl-8-quinolinato)(o-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, and bis(2-methyl-8-quinolinato)(2-naphthol)gallium.

[0248] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the electron injection layer. Examples include, but are not limited to, diazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0249] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type depending on the materials used.

[0250] The organic light-emitting device of the present invention uses the above-mentioned compound to form one or more organic layers, and can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0251] The method for producing the compound of Chemical Formula 1 and the production of an organic light-emitting device using the same are specifically described in the following examples. However, the following examples are provided to illustrate the present invention and the scope of the present invention is not limited thereto.

[0252] In the following reaction formula, the type and number of substituents can be appropriately selected by those skilled in the art from known starting materials to synthesize various types of intermediates. The type and reaction conditions can utilize techniques known in the art.

[0253] 1) Preparation of Compound E1

[0254]

[0255] Under nitrogen atmosphere, E1-A (20 g, 47.7 mmol) and E1-B (29.44 g, 52.5 mmol) were added to 400 ml of 1,4-dimethoxybenzyl alcohol. The mixture was added to 1,4-dioxane, stirred and refluxed. Potassium phosphate (30.4 g, 143.2 mmol) was then dissolved in 150 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0.35 g, 0.48 mmol) was added. After reacting for 6 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was added to 2000 ml of chloroform and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound E1 (21.0 g, 53.8%).

[0256] MS:[M+H] + =818

[0257] 2) Preparation of Compound E2

[0258]

[0259] The compound E2 was produced by the same method as in Production Example 1 except that the starting materials E2-A and E2-B were used.

[0260] MS:[M+H] + =818

[0261] 3) Preparation of Compound E3

[0262]

[0263] The compound E3 was produced by the same method as in Production Example 1 except that the starting materials E3-A and E3-B were used.

[0264] MS:[M+H] + =894

[0265] 4) Preparation of Compound E4

[0266]

[0267] The compound E4 was produced by the same method as in Production Example 1 except that the starting materials E4-A and E4-B were used.

[0268] MS:[M+H] + =868

[0269] 5) Preparation of Compound E5

[0270]

[0271] The compound E5 was produced by the same method as in Production Example 1 except that the starting materials E5-A and E5-B were used.

[0272] MS:[M+H] + =867

[0273] 6) Preparation of Compound E6

[0274]

[0275] The compound E6 was produced by the same method as in Production Example 1 except that the starting materials E6-A and E6-B were used.

[0276] MS:[M+H] + =969

[0277] 7) Preparation of Compound E7

[0278]

[0279] The compound E7 was produced by the same method as in Production Example 1 except that the starting materials E7-A and E7-B were used.

[0280] MS:[M+H] + =768

[0281] 8) Preparation of Compound E8

[0282]

[0283] The compound E8 was produced by the same method as in Production Example 1 except that the starting materials E8-A and E8-B were used.

[0284] MS:[M+H] + =768

[0285] 9) Preparation of Compound E9

[0286]

[0287] The compound E9 was produced by the same method as in Production Example 1 except that the starting materials E9-A and E9-B were used.

[0288] 10) Preparation of Compound E10

[0289] MS:[M+H] + =795

[0290]

[0291] The compound E10 was produced by the same method as in Production Example 1 except that the starting materials E10-A and E10-B were used.

[0292] MS:[M+H] + =795

[0293] All the compounds of the above Chemical Formula 1 described in the present specification can be produced by appropriately combining the production formulas described in the Examples of the present specification and the above intermediates based on common technical knowledge.

[0294] Example 1

[0295] ITO (Indium Tin Oxide) The glass substrate coated with a film of a thickness of 100 nm was placed in distilled water dissolved with detergent and washed with ultrasound. At this time, the detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice by a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaning machine. In addition, after cleaning the above-mentioned substrate with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporation machine. On the ITO transparent electrode prepared in this way, the following compound HI-A was applied with The hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT, ) and the following compound HT-A Then, a hole transport layer is formed by vacuum evaporation. The following compounds BH and BD were vacuum-deposited at a weight ratio of 25:1 to form a light-emitting layer. On the above-mentioned light-emitting layer, the compound E1 prepared in Preparation Example 1 and the following compound LiQ (lithium quinolate) were vacuum-deposited at a weight ratio of 1:1 to form a light-emitting layer. The electron injection and transport layer is formed with a thickness of The thickness of the aluminum The cathode is formed by evaporation to a thickness of .

[0296]

[0297] In the above process, the evaporation rate of organic matter is maintained at Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 1*10 -7 ~5*10 -8 The organic light-emitting device is thus produced.

[0298] Examples 2 to 10

[0299] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compound shown in Table 1 below was used instead of Compound E1 in Example 1.

[0300] Comparative Examples 1 to 7

[0301] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compound shown in Table 1 below was used instead of Compound E1 in Example 1. Compounds ET1 to ET7 used in Table 1 below are shown below.

[0302]

[0303] For the organic light emitting devices manufactured in Examples 1 to 10 and Comparative Examples 1 to 7, the 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA / cm 2 The time (T90) required for the luminance to reach 90% of the initial luminance was measured at a current density of 1.5 Å. The results are shown in Table 1 below.

[0304]

Table 1

[0305]

[0306] In the compound ET1 used in Comparative Example 1, the terphenyl core is in a para-position and unsubstituted form, and the bonding position of the triazine is in a meta-position.

[0307] In Comparative Examples 2 to 5, the core terphenyl was in the ortho- or meta-form, and unsubstituted compounds were also used.

[0308] For Comparative Examples 6 and 7, compounds in which the terphenyl nucleus was not substituted with a substituted or unsubstituted aryl group were used.

[0309] Compounds E1 to E10 used in the examples differ from the compounds used in comparative examples 1 to 7 in that the para-form terphenyl is substituted with one or more aryl or heteroaryl groups, and triazine and other N-containing monocyclic rings are para-bonded to both ends of the terphenyl.

[0310] Examples 1 to 10 using the compound of Chemical Formula 1 of the present invention showed the effects of low voltage, high efficiency, and long life compared to Comparative Examples 1 to 7 not using the compound of Chemical Formula 1 of the present invention.

[0311] As shown in Table 1, the organic light-emitting device of the example manufactured using the compound represented by Chemical Formula 1 of the present invention has a lower driving voltage than the organic light-emitting device of the comparative example and exhibits excellent characteristics in terms of efficiency and lifespan.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, At least one of X1 to X3 is N, and the rest are CR, At least one of X4 to X6 is N, and the rest are CR. R is hydrogen, deuterium, nitrile, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amino, or substituted or unsubstituted heteroaryl, At least one of R1 to R3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and the others are the same as or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted heteroaryl group, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, a to c are each an integer from 1 to 4, When a is 2 or more, R1 are the same or different. When b is 2 or more, R2 are the same or different. When c is 2 or more, R3 are the same as or different from each other.

2. The compound according to claim 1, wherein One of R1 to R3 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and the others are the same as or different from each other and are independently hydrogen, deuterium or nitrile.

3. The compound according to claim 1, wherein Two of the R1 to R3 are the same as or different from each other, and are independently substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and the rest are hydrogen, deuterium or nitrile.

4. The compound according to claim 1, wherein The Ar1 and Ar2 are identical to each other.

5. The compound according to claim 1, wherein The Ar1 and Ar2 are different from each other.

6. The compound according to claim 1, wherein Ar3 and Ar4 are identical to each other.

7. The compound according to claim 1, wherein Ar3 and Ar4 are different from each other.

8. The compound according to claim 1, wherein One of Ar1 to Ar4 is an aryl group having 10 to 30 carbon atoms, and the others are the same as or different from each other and are independently substituted or unsubstituted aryl groups.

9. The compound according to claim 1, wherein Two of the Ar1 to Ar4 are the same or different and are independently an aryl group having 10 to 30 carbon atoms, and the rest are the same or different and are independently a substituted or unsubstituted aryl group.

10. The compound according to claim 1, wherein The chemical formula 1 is any one of the following compounds:

11. An organic light-emitting device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 10.

12. The organic light emitting device according to claim 11, wherein The organic 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 contains the compound.

13. The organic light emitting device according to claim 12, wherein: The electron injection and transport layer contains both a metal complex and the compound.

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