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. 10-2023-0131553 filed with the Korean Intellectual Property Office on October 4, 2023, the entire contents of which are incorporated herein by reference.

[0002] This application claims the priority of Korean Patent Application No. 10-2024-0108845 filed with the Korean Patent Office on August 14, 2023, the entire contents of which are incorporated herein by reference.

[0003] The present invention relates to a compound and an organic light-emitting device including the same. Background Art

[0004] In this specification, an organic light-emitting device refers to a light-emitting device that utilizes an organic semiconductor material, which 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 utilizes photons flowing into the device from an external light source to form excitons in an organic layer, and the excitons are separated into electrons and holes, which are respectively transferred to different electrodes and used as a current source (voltage source). The second type is a light-emitting device that applies a voltage or current to two or more electrodes, thereby injecting holes and / or electrons into an organic semiconductor material layer that forms an interface with the electrodes, and works through the injected electrons and holes.

[0005] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light-emitting device using the organic light-emitting phenomenon generally has a structure including an anode and a cathode and an organic layer located between them. 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 blocking 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 re-transition to the ground state, light is emitted. Such organic light-emitting devices are known to have the characteristics of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, etc.

[0006] Materials used as organic layers in organic light-emitting devices can be divided into light-emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron suppression materials, electron transport materials, electron injection materials, etc. According to the luminescent color, the light-emitting materials include blue, green, and red light-emitting materials, as well as yellow and orange light-emitting materials required to achieve better natural colors.

[0007] In addition, in order to increase the color purity and increase the luminous efficiency based on energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a dopant with a smaller energy band gap and excellent luminous efficiency than the host that mainly constitutes the luminescent layer is mixed in a small amount into the luminescent layer, the excitons generated in the host are transferred to the dopant and emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength range of the dopant, light of the desired wavelength can be obtained according to the type of dopant used.

[0008] In order to give full play to the excellent characteristics of the above-mentioned organic light-emitting devices, the substances constituting 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.

[0009] Prior art literature

[0010] Patent Literature

[0011] (Patent Document 1) International Patent Publication No. 2017-126443 Summary of the invention

[0012] Technical issues

[0013] This specification describes a compound and an organic light-emitting device including the same.

[0014] Solution to the problem

[0015] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0016] [Chemical formula 1]

[0017]

[0018] In Chemical Formula 1,

[0019] L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0020] Ar is a substituted or unsubstituted monocyclic or bicyclic N-containing heteroaryl group,

[0021] R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0022] a and c are integers from 1 to 4,

[0023] b is an integer from 1 to 3,

[0024] d and e are integers from 1 to 5,

[0025] When a is 2 or more, R1 are the same or different from each other.

[0026] When b is 2 or more, R2 are the same or different from each other,

[0027] When c is 2 or more, R3 are the same or different from each other,

[0028] When d is 2 or more, R4 are the same or different from each other,

[0029] When e is 2 or more, R5 are the same as or different from each other.

[0030] 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.

[0031] Effects of the Invention

[0032] 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 life characteristics can be obtained. When the compound of the present invention is included in an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole blocking layer of an organic light-emitting device, an organic light-emitting device having low voltage, high efficiency and long life characteristics can be manufactured. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 and 2 An example of an organic light emitting device according to the present invention is illustrated.

[0034] Explanation of symbols

[0035] 1: Substrate

[0036] 2: First electrode

[0037] 3: Organic layer

[0038] 4: Second electrode

[0039] 5: Hole injection layer

[0040] 6: Hole transport layer

[0041] 7: Electron blocking layer

[0042] 8: Luminous layer

[0043] 9: Hole blocking layer

[0044] 10: Electron injection and transport layer DETAILED DESCRIPTION

[0045] Next, this specification is described in more detail.

[0046] Compared with the commonly used electron transport layer, the compound of chemical formula 1 of the present invention shortens the connecting group between the N-containing ring groups, and makes the direction of the connecting group substituted to the ortho position and the meta position, thereby minimizing conjugation and giving steric hindrance to maximize the flow and efficiency of electrons. In addition, the CN group with a large electronegative substituent to extend the life also shows a long life characteristic.

[0047] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.

[0048] In the present specification, when it is mentioned that a certain member is located “on” another member, it includes not only a case where the certain member is in contact with the other member but also a case where other members are present between the two members.

[0049] The term "substituted" mentioned above means that the hydrogen atom bonded to the carbon atom of the compound is replaced by another substituent. The substituted position 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 more than two substitutions, the two or more substituents may be the same or different from each other.

[0050] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, cyano groups (-CN), silyl groups, boron groups, alkyl groups, cycloalkyl groups, aryl groups, and heterocyclic groups, or substituted by a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituents. For example, "a substituent formed by connecting two or more substituents" can be a biphenyl group. That is, the biphenyl group can be an aryl group, and can also be interpreted as a substituent formed by connecting two phenyl groups.

[0051] Examples of the above substituents are described below, but are not limited thereto.

[0052] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0053] In the present specification, the silyl group can be represented by the chemical formula -SiY1Y2Y3, and the above Y1, Y2 and Y3 can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The above silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0054] In this specification, the boron group can be represented by the chemical formula -BY4Y5, and each of Y4 and Y5 can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The boron group specifically includes dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, phenylboryl, etc., but is not limited thereto.

[0055] 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 one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc., but are not limited thereto.

[0056] In the present 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 number of carbon atoms of the alkyl group is 1 to 30, and the number of carbon atoms of the aryl group substituted in the alkyl group is 6 to 30.

[0057] In the present specification, the amine group can be selected from -NH2; alkylamine; N-alkylarylamine; arylamine; N-arylheteroarylamine; N-alkylheteroarylamine and heteroarylamine, 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, anthracenylamino, 9-methylanthrylamino, diphenylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, and N-biphenylfluorenylamino.

[0058] In the present specification, the 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.

[0059] In the present specification, the 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.

[0060] In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroaryl group are substituted on the nitrogen of the amine group.

[0061] In this specification, alkylamino, N-arylalkylamino, alkylthio Alkylsulfonyl The alkyl group in the N-alkylheteroarylamine group is the same as the alkyl group exemplified above. Specifically, as the alkylthio group, there are methylthio, ethylthio, tert-butylthio, hexylthio, octylthio, etc., and as the alkylsulfonyl group, there are methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, etc., but it is not limited thereto.

[0062] In the present 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. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0063] In the present 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 it 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 to these.

[0064] In the present specification, the heteroaryl group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but 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 the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, etc., but are not limited thereto.

[0065] In the present specification, the meaning of “adjacent” in “bonding to adjacent groups to form a ring” is the same as defined above, and the above “ring” refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0066] In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and except for not being monovalent as mentioned above, may be selected from the examples of the above-mentioned cycloalkyl group, aryl group, and combinations thereof, and the above-mentioned hydrocarbon rings include benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2,3,4-tetrahydro-1,4-methylenenaphthalene and 1,2,3,4-tetrahydro-1,4-ethylenenaphthalene, but are not limited thereto.

[0067] In the present specification, an arylene group is a divalent group, and other than this, has the same definition as in the above-mentioned aryl group.

[0068] In the present specification, the heteroarylene group is the same as defined in the above-mentioned heteroaryl group except that it is a divalent group.

[0069] 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 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, and 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 only illustrative and not intended to be limited.

[0070] In the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-1 to 1-4.

[0071] [Chemical formula 1-1]

[0072]

[0073] [Chemical formula 1-2]

[0074]

[0075] [Chemical formula 1-3]

[0076]

[0077] [Chemical formula 1-4]

[0078]

[0079] In the above Chemical Formulae 1-1 to 1-4, the above R1 to R5, L, Ar, and a to e are the same as defined in the above Chemical Formula 1.

[0080] In this specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 2-1 to 2-3.

[0081] [Chemical formula 2-1]

[0082]

[0083] [Chemical formula 2-2]

[0084]

[0085] [Chemical formula 2-3]

[0086]

[0087] In the above Chemical Formulae 2-1 to 2-3, the above R1 to R5, L, Ar, and a to e are the same as defined in the above Chemical Formula 1.

[0088] In the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulas 1-11 to 1-22.

[0089] [Chemical formula 1-11]

[0090]

[0091] [Chemical formula 1-12]

[0092]

[0093] [Chemical formula 1-13]

[0094]

[0095] [Chemical formula 1-14]

[0096]

[0097] [Chemical formula 1-15]

[0098]

[0099] [Chemical formula 1-16]

[0100]

[0101] [Chemical formula 1-17]

[0102]

[0103] [Chemical formula 1-18]

[0104]

[0105] [Chemical formula 1-19]

[0106]

[0107] [Chemical formula 1-20]

[0108]

[0109] [Chemical formula 1-21]

[0110]

[0111] [Chemical formula 1-22]

[0112]

[0113] In the above Chemical Formulae 1-11 to 1-22, the above R1 to R5, L, Ar, and a to e are the same as defined in the above Chemical Formula 1.

[0114] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0115] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro 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, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0116] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, an alkyl group, an aryl group or a heteroaryl group.

[0117] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0118] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0119] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, or an alkyl group having 1 to 10 carbon atoms.

[0120] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, methyl, ethyl or propyl.

[0121] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, methyl or ethyl.

[0122] In the present specification, the above R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium or nitro.

[0123] In the present specification, the above R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, an alkyl group, an aryl group or a heteroaryl group.

[0124] In the present specification, the above R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0125] In the present specification, the above R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0126] In the present specification, the above R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, or an alkyl group having 1 to 10 carbon atoms.

[0127] In the present specification, the above R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, methyl, ethyl or propyl.

[0128] In the present specification, the above R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, methyl or ethyl.

[0129] In the present specification, the above R1 to R3 are the same as or different from each other, and are each independently hydrogen, deuterium or nitro.

[0130] In the present specification, the above R4 and R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, an alkyl group, an aryl group or a heteroaryl group.

[0131] In the present specification, the above R4 and R5 are the same as or different from each other, and are independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0132] In the present specification, R4 and R5 are the same as or different from each other, and are independently hydrogen, deuterium, nitro, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0133] In the present specification, the above R4 and R5 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, or an alkyl group having 1 to 10 carbon atoms.

[0134] In the present specification, the above R4 and R5 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, methyl, ethyl or propyl.

[0135] In the present specification, the above R4 and R5 are the same as or different from each other, and are each independently hydrogen, deuterium, nitro, methyl or ethyl.

[0136] In the present specification, the above R4 and R5 are the same as or different from each other, and are each independently hydrogen, deuterium or nitro.

[0137] In the present specification, the above-mentioned R1 to R5 are hydrogen.

[0138] In the present specification, the above-mentioned R1 to R5 are deuterium.

[0139] In the present specification, the above R1 to R5 are hydrogen or nitro.

[0140] In the present specification, the above-mentioned R1 to R3 are hydrogen.

[0141] In the present specification, the above-mentioned R1 to R3 are deuterium.

[0142] In the present specification, the above R1 to R3 are hydrogen or nitro.

[0143] In the present specification, the above-mentioned R4 and R5 are hydrogen.

[0144] In the present specification, the above-mentioned R4 and R5 are deuterium.

[0145] In the present specification, the above R4 and R5 are hydrogen or nitro.

[0146] In the present specification, the above-mentioned L is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

[0147] In the present specification, the above-mentioned L is a direct bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 25 carbon atoms.

[0148] In the present specification, the above-mentioned L is a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0149] In the present specification, the above-mentioned L is a direct bond, a substituted or unsubstituted arylene group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 15 carbon atoms.

[0150] In the present specification, the above-mentioned L is a direct bond, or a monocyclic or bicyclic arylene group.

[0151] In the present specification, the above-mentioned L is a direct bond, a phenylene group, or a divalent naphthyl group.

[0152] In this specification, the above-mentioned L is a direct bond.

[0153] In the present specification, the above-mentioned Ar is a substituted or unsubstituted monocyclic or bicyclic N-containing heteroaryl group.

[0154] In the present specification, the above-mentioned Ar is a N-containing monocyclic or bicyclic heteroaryl group substituted with an alkyl group or an aryl group.

[0155] In the present specification, the above-mentioned Ar is a substituted or unsubstituted monocyclic N-containing heteroaryl group.

[0156] In the present specification, the above-mentioned Ar is a monocyclic N-containing heteroaryl group.

[0157] In the present specification, the above-mentioned Ar is a pyrimidinyl group, a pyridyl group or a triazine group, and the above-mentioned pyrimidinyl group, a pyridyl group or a triazine group is substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, a nitrile group, an alkyl group, an aryl group and a heteroaryl group.

[0158] In the present specification, the above-mentioned Ar is a pyrimidinyl group, a pyridyl group or a triazine group, and the above-mentioned pyrimidinyl group, the pyridyl group or the triazine group is substituted with one or more substituents selected from deuterium, a nitrile group, an alkyl 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.

[0159] In the present specification, the above Ar is a pyrimidinyl, pyridinyl or triazinyl group, and the above pyrimidinyl, pyridinyl or triazinyl group is selected from deuterium, nitrile, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, quinazolyl The benzimidazolyl group and the triazine group are substituted with one or more substituents.

[0160] In the present specification, the above-mentioned Ar is a substituted or unsubstituted bicyclic N-containing heteroaryl group.

[0161] In the present specification, the above-mentioned Ar is a bicyclic N-containing heteroaryl group.

[0162] In the present specification, the above-mentioned Ar is a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted quinoxalinyl group, or a substituted or unsubstituted quinazoline group.

[0163] In the present specification, the above Ar is benzimidazolyl, quinolyl, quinoxalinyl or quinazolinyl, and the above benzimidazolyl, quinolyl, quinoxalinyl or quinazolinyl is substituted with one or more substituents selected from deuterium, nitrile, alkyl, aryl and heteroaryl.

[0164] In the present specification, the above-mentioned Ar is a benzimidazolyl group, a quinolyl group or a quinazolinyl group, and the above-mentioned benzimidazolyl group, a quinolyl group or a quinazolinyl group is substituted with one or more substituents selected from the group consisting of deuterium, a nitrile group, an alkyl group, an aryl group and a heteroaryl group.

[0165] In the present specification, the above-mentioned Ar is a benzimidazolyl group, a quinolyl group or a quinazolinyl group, and the above-mentioned benzimidazolyl group, a quinolyl group or a quinazolinyl group is substituted with one or more substituents selected from deuterium, a nitrile group, an alkyl 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.

[0166] In the present specification, the above-mentioned Ar is a benzimidazolyl group, a quinolyl group or a quinazolinyl group, and the above-mentioned benzimidazolyl group, a quinolyl group or a quinazolinyl group is substituted with one or more substituents selected from deuterium, a nitrile group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridyl group, a pyrimidinyl group, a quinazolyl group, a benzimidazolyl group and a triazine group.

[0167] In the present specification, Ar is pyrimidinyl, pyridyl, triazine, benzimidazolyl, quinolyl or quinazolinyl.

[0168] The above-mentioned pyrimidinyl, pyridyl, triazine, benzimidazolyl, quinolyl or quinazolinyl is substituted with one or more substituents selected from deuterium, nitrile, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinazolyl, benzimidazolyl and triazine.

[0169] In the present specification, the above Chemical Formula 1 is any one of the following structural formulas.

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178] The substituents of the compound of the above 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.

[0179] In addition, by introducing various substituents into the core structure of the structure shown above, compounds having the inherent characteristics of the introduced substituents can be synthesized. For example, substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices are introduced into the above core structure, so that substances that meet the conditions required for each organic layer can be synthesized.

[0180] 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.

[0181] 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.

[0182] The above compounds can be formed into an organic layer by not only vacuum evaporation method but also solution coating method when manufacturing organic light-emitting devices. Here, the so-called solution coating method refers to spin coating method, dip coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0183] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers or a larger number of organic layers.

[0184] In the organic light-emitting device of the present invention, the organic layer may include one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more of the layers may contain the compound represented by Chemical Formula 1.

[0185] 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 includes the compound represented by Chemical Formula 1.

[0186] In another organic light-emitting device, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound.

[0187] In one embodiment of the present specification, a light-emitting layer is included between the electron injection layer, the electron transport layer, or the electron injection and transport layer and the anode.

[0188] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0189] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0190] (1) Anode / hole transport layer / light-emitting layer / cathode

[0191] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0192] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0193] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0194] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0195] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0196] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0197] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0198] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0199] (10) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0200] (11) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0201] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0202] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0203] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0204] (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0205] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0206] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0207] (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0208] The structure of the organic light emitting device of the present invention may have the following Figure 1 and 2 The structure shown is not limited thereto.

[0209] 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 the above Chemical Formula 1 may be contained in the above organic layer 3.

[0210] Figure 2 The structure of an organic light-emitting device is illustrated in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron injection and transport layer 10, and a second electrode 4 are sequentially stacked on a substrate 1.

[0211] In the structure as described above, the compound represented by the above Chemical Formula 1 may be included in the above hole blocking layer 9 and the electron injection and transport layer 10 .

[0212] For example, the organic light-emitting device according to the present invention can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate by a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, and then an organic layer including one or more layers selected from a hole injection layer, a hole transport layer, a layer for simultaneously performing hole transport and hole injection, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer for simultaneously performing electron transport and electron injection is formed on the anode, and then a substance that can be used as a cathode is deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0213] The organic layer may be 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 be a single layer structure. In addition, the organic layer may be made of various polymer materials and formed into a smaller number of layers by a solvent process other than evaporation, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0214] The anode is an electrode for injecting holes. As the anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2: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.

[0215] The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0216] The hole injection layer is a layer that plays a role in making the injection of holes from the anode to the light-emitting layer smooth. The hole injection material is a material that can well receive holes from the anode at a low voltage. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrines, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited to this. The thickness of the hole injection layer can be 1 to 150nm. When the thickness of the hole injection layer is more than 1nm, it has the advantage of preventing the hole injection characteristics from being reduced. When it is less than 150nm, it has the advantage of preventing the driving voltage from rising when the thickness of the hole injection layer is too thick to increase the movement of holes.

[0217] 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.

[0218] [Chemical formula HI-1]

[0219]

[0220] In the above chemical formula HI-1,

[0221] R400 to R402 are the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0222] L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0223] According to one embodiment of the present specification, the above 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 amine group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0224] According to one embodiment of the present specification, R402 is any one selected from a phenyl group substituted with a carbazolyl group or an arylamine group, a biphenyl group substituted with a carbazolyl group or an arylamine group, and a combination thereof.

[0225] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and are independently substituted or unsubstituted aryl groups, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0226] 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 by an alkyl group or not.

[0227] 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 dimethylfluorenyl group.

[0228] According to one embodiment of the present specification, the chemical formula HI-1 is selected from the following compounds.

[0229]

[0230] According to one embodiment of the present specification, the hole injection layer includes a compound represented by the following chemical formula HI-2, but the present invention is not limited thereto.

[0231] [Chemical formula HI-2]

[0232]

[0233] In the above chemical formula HI-2,

[0234] X'1 to X'3 are the same as or different from each other, and are each independently hydrogen, deuterium or a halogen group,

[0235] 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 amine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0236] Each of x1' to x3' is an integer of 1 to 4, and when they are 2 or more, the substituents in the brackets are the same as or different from each other.

[0237] According to one embodiment of the present specification, the aforementioned X'1 to X'3 are halogen groups.

[0238] According to one embodiment of the present specification, X'1 to X'3 are F or Cl.

[0239] According to one embodiment of the present specification, X'1 to X'3 are F.

[0240] According to one embodiment of the present specification, R309 to R314 are the same as or different from each other, and are independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted amine group.

[0241] According to one embodiment of the present specification, R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium or a nitrile group.

[0242] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0243] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0244]

[0245] The hole transport layer can play a role in smoothing the transport of holes. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers with both conjugated parts and non-conjugated parts, but are not limited to these.

[0246] According to one 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.

[0247] [Chemical formula HT-2]

[0248]

[0249] In the above chemical formula HT-2,

[0250] R403 to R406 are the same as or different from each other, and are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted amine, substituted or unsubstituted heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0251] L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0252] l403 is an integer from 1 to 3. When l403 is 2 or more, L403 are the same as or different from each other.

[0253] 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 amine group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0254] 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.

[0255] 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 or a naphthyl group.

[0256] 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.

[0257] 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.

[0258] According to one embodiment of the present specification, the L403 is a phenylene group, a divalent biphenyl group, or a divalent carbazolyl group which may be substituted with an aryl group.

[0259] According to one embodiment of the present specification, the above-mentioned L403 is a divalent carbazole group substituted with a phenyl group.

[0260] According to one embodiment of the present specification, the chemical formula HT-2 is selected from the following compounds.

[0261]

[0262] 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.

[0263] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may use the above-mentioned spiro compound or a material known in the art.

[0264] According to one embodiment of the present specification, the electron blocking layer includes a compound represented by the following chemical formula EB-1, but is not limited thereto.

[0265] [Chemical formula EB-1]

[0266]

[0267] In the above chemical formula EB-1,

[0268] R318 to R320 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 heteroaryl, and any combination thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0269] r318 is an integer from 1 to 5. When the above r318 is 2 or more, the two or more R318 are the same or different from each other.

[0270] r319 is an integer of 1 to 5. When the number of r319 is 2 or more, the two or more R319s are the same as or different from each other.

[0271] According to one embodiment of the present specification, the above R320 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0272] According to one embodiment of the present specification, the above-mentioned R320 is a carbazole group.

[0273] According to one embodiment of the present specification, R318 and R319 are the same as or different from each other, and are independently substituted or unsubstituted aryl groups, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0274] According to one embodiment of the present specification, R318 and R319 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group or a phenanthryl group.

[0275] According to one embodiment of the present specification, the chemical formula EB-1 is represented by the following compound.

[0276]

[0277] The above-mentioned light-emitting layer can emit red, green or blue light, and can be formed of a phosphorescent material or a fluorescent material. The above-mentioned 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. As specific examples, there are 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0278] The main 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 to these.

[0279] 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.

[0280] [Chemical formula H-1]

[0281]

[0282] In the above chemical formula H-1,

[0283] 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,

[0284] Ar20 and Ar21 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0285] 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,

[0286] 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.

[0287] 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.

[0288] 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.

[0289] In one embodiment of the present specification, the Ar20 is a substituted or unsubstituted heterocyclic group, and the Ar21 is a substituted or unsubstituted aryl group.

[0290] 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.

[0291] 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.

[0292] 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; Thienyl substituted or unsubstituted by an aryl group having 6 to 20 carbon atoms; dibenzofuranyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; naphthobenzofuranyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; dibenzothienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or naphthobenzothienyl substituted or unsubstituted by a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0293] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted by deuterium, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group, a naphthyl group substituted or unsubstituted by deuterium, a thienyl group substituted or unsubstituted by phenyl, a phenanthryl group, a dibenzofuranyl group, a naphthiobenzofuranyl group, a dibenzothiophenyl group, or a naphthiobenzothiophenyl group.

[0294] 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.

[0295] According to one embodiment of the present specification, the above R201 is hydrogen.

[0296] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0297]

[0298] When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent materials 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 materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, Ir(ppy)3(faq) can be used. tris(2-phenylpyridine)iridium, tris(2-phenylpyridine)iridium, or Alq3(tris(8-hydroxyquinoline)aluminum) or other phosphorescent materials, but not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used; or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, PPV-based polymers can be used, but not limited to these.

[0299] According to one embodiment of the present specification, the dopant is represented by a compound of the following chemical formula D-2.

[0300] [Chemical formula D-2]

[0301]

[0302] In the above chemical formula D-2,

[0303] T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted amine group, or a substituted or unsubstituted aryl group,

[0304] t3 and t4 are each an integer from 1 to 4,

[0305] t5 is an integer from 1 to 3,

[0306] When the above t3 is 2 or more, the above two or more T3 are the same or different from each other.

[0307] When the above t4 is 2 or more, the above two or more T4 are the same or different from each other.

[0308] When the above t5 is 2 or more, the above two or more T5s may be the same as or different from each other.

[0309] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0310] According to one embodiment of the present specification, the above-mentioned T1 to T5 are the same as or different from each other, and are each independently hydrogen, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.

[0311] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are independently hydrogen, methyl, isopropyl, tert-butyl, diphenylamino, or phenyl which may be substituted or unsubstituted by methyl or tert-butyl.

[0312] According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound.

[0313]

[0314] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the technical field may be used.

[0315] 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 receive electrons well from the cathode and transfer them to the light-emitting layer, and is suitable for materials with high electron mobility. 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 this. The thickness of the electron transport layer can be 1 to 50nm. When the thickness of the electron transport layer is more than 1nm, it has the advantage of preventing the electron transport characteristics from being reduced. When it is less than 50nm, it has the advantage of preventing the driving voltage from rising in order to increase the movement of electrons when the thickness of the electron transport layer is too thick.

[0316] 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 an excellent electron injection effect 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.

[0317] The electron injection and transport layer can play a role in facilitating electron injection and transport. As the electron injection and transport material, the above-mentioned material for facilitating electron injection and material for facilitating transport can be used.

[0318] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0319] 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 of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0320] According to one embodiment of the present specification, the hole blocking layer includes a compound of the following chemical formula HB-1.

[0321] [Chemical formula HB-1]

[0322]

[0323] In the above chemical formula HB-1,

[0324] At least one of Z1 to Z3 is N, and the others are CH,

[0325] L601 and L602 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 heteroarylene group,

[0326] Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0327] According to one embodiment of the present specification, the above L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0328] According to one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently a phenylene group, a biphenylene group, or a naphthylene group.

[0329] According to one embodiment of the present specification, Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0330] According to one embodiment of the present specification, Ar601 to Ar603 are phenyl or dimethylfluorenyl.

[0331] According to one embodiment of the present specification, the chemical formula HB-1 is represented by the following compound.

[0332]

[0333] 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 according to the materials used.

[0334] 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.

[0335] The method for producing the compound of the above 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 used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0336] In the following reaction formula, the type and number of substituents can be appropriately selected by a person skilled in the art from known starting materials to synthesize various types of intermediates. The reaction type and reaction conditions can utilize techniques known in the art.

[0337] Preparation Example 1. Synthesis of Compound E1

[0338] [Compound E1]

[0339]

[0340] After the above-mentioned compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazinyl) (10.0 g, 15.4 mmol) and (3-cyanophenyl)boric acid (2.25 g, 15.4 mmol) were completely dissolved in tetrahydrofuran (100 ml), potassium carbonate (6.4 g, 46.2 mmol) was dissolved in 19 ml of water and added, and tetrakis(triphenylphosphine)palladium (534 mg, 0.5 mmol) was dissolved in tetrahydrofuran and slowly added. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate solution was removed and the above-mentioned white solid was filtered. The filtered white solid was washed twice with water and ethyl acetate, respectively, to produce the above-mentioned compound E1 (9.9 g, yield 90%).

[0341] MS[M+H] + =717

[0342] Preparation Example 2. Compound E2

[0343] [Compound E2]

[0344]

[0345] The above-mentioned compound E2 was produced by the same method as in the above-mentioned Production Example 1, except that 6,6'-(6-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazinyl) was used instead of the above-mentioned 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazinyl).

[0346] MS[M+H] + =717

[0347] Preparation Example 3. Synthesis of Compound E3

[0348] [Compound E3]

[0349]

[0350] The above-mentioned compound E3 was produced by the same method as in the above-mentioned Production Example 1, except that 6,6'-(3-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazinyl) was used instead of the above-mentioned 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazinyl).

[0351] MS[M+H] +=717

[0352] Preparation Example 4. Synthesis of Compound E4

[0353] [Compound E4]

[0354]

[0355] The compound E4 was produced by the same method as in Production Example 1, except that 6,6'-(4-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazinyl) was used instead of 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazinyl).

[0356] MS[M+H] + =717

[0357] Preparation Example 5. Synthesis of Compound E5

[0358] [Compound E5]

[0359]

[0360] The compound E5 was produced by the same method as in Production Example 4 except that (4-cyanophenyl)boronic acid was used instead of (3-cyanophenyl)boronic acid.

[0361] MS[M+H] + =717

[0362] Preparation Example 6. Synthesis of Compound E6

[0363] [Compound E6]

[0364]

[0365] The compound E6 was produced by the same method as in Production Example 3 except that (4-cyanophenyl)boronic acid was used instead of (3-cyanophenyl)boronic acid.

[0366] MS[M+H] + =717

[0367] Preparation Example 7. Synthesis of Compound E7

[0368] [Compound E7]

[0369]

[0370] The compound E7 was produced by the same method as in Production Example 2 except that (4-cyanophenyl)boronic acid was used instead of (3-cyanophenyl)boronic acid.

[0371] MS[M+H] + =717

[0372] Preparation Example 8. Synthesis of Compound E8

[0373] [Compound E8]

[0374]

[0375] The compound E8 was produced by the same method as in Production Example 1, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0376] MS[M+H] + =717

[0377] Preparation Example 9. Synthesis of Compound E9

[0378] [Compound E9]

[0379]

[0380] The compound E9 was produced by the same method as in Production Example 1, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0381] MS[M+H] + =717

[0382] Preparation Example 10. Synthesis of Compound E10

[0383] [Compound E10]

[0384]

[0385] The compound E10 was produced by the same method as in Production Example 2 except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0386] MS[M+H] + =717

[0387] Preparation Example 11. Synthesis of Compound E11

[0388] [Compound E11]

[0389]

[0390] The compound E11 was produced by the same method as in Production Example 3, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0391] MS[M+H] + =717

[0392] Preparation Example 12. Synthesis of Compound E12

[0393] [Compound E12]

[0394]

[0395] The compound E12 was produced by the same method as in Production Example 4, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0396] MS[M+H] + =717

[0397] Preparation Example 13. Synthesis of Compound E13

[0398] [Compound E13]

[0399]

[0400] The compound E13 was produced by the same method as in Production Example 1, except that 2-(5'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-4-phenylquinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0401] MS[M+H] + =690

[0402] Preparation Example 14. Synthesis of Compound E14

[0403] [Compound E14]

[0404]

[0405] The compound E14 was produced by the same method as in Production Example 13, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0406] MS[M+H] +=690

[0407] Preparation Example 15. Synthesis of Compound E15

[0408] [Compound E15]

[0409]

[0410] The compound E15 was produced by the same method as in Production Example 13, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0411] MS[M+H] + =690

[0412] Preparation Example 16. Synthesis of Compound E16

[0413] [Compound E16]

[0414]

[0415] The compound E16 was produced by the same method as in Production Example 1, except that 2-(4'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-4-phenylquinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0416] MS[M+H] + =690

[0417] Preparation Example 17. Synthesis of Compound E17

[0418] [Compound E17]

[0419]

[0420] The compound E17 was produced by the same method as in Production Example 16, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0421] MS[M+H] + =690

[0422] Preparation Example 18. Synthesis of Compound E18

[0423] [Compound E18]

[0424]

[0425] The compound E18 was prepared by the same method as in Preparation Example 16 except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0426] MS[M+H] + =690

[0427] Preparation Example 19. Synthesis of Compound E19

[0428] [Compound E19]

[0429]

[0430] The compound E19 was produced by the same method as in Production Example 1, except that 2-(3'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-4-phenylquinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0431] MS[M+H] + =690

[0432] Preparation Example 20. Synthesis of Compound E20

[0433] [Compound E20]

[0434]

[0435] The compound E20 was produced by the same method as in Production Example 19, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0436] MS[M+H] + =690

[0437] Preparation Example 21. Synthesis of Compound E21

[0438] [Compound E21]

[0439]

[0440] The compound E21 was produced by the same method as in Production Example 19, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0441] MS[M+H] + =690

[0442] Preparation Example 22. Synthesis of Compound E22

[0443] [Compound E22]

[0444]

[0445] The compound E22 was produced by the same method as in Production Example 1, except that 2-(2'-chloro-6'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-4-phenylquinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0446] MS[M+H] + =690

[0447] Preparation Example 23. Synthesis of Compound E23

[0448] [Compound E23]

[0449]

[0450] The compound E23 was produced by the same method as in Production Example 22, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0451] MS[M+H] + =690

[0452] Preparation Example 24. Synthesis of Compound E24

[0453] [Compound E24]

[0454]

[0455] The compound E24 was produced by the same method as in Production Example 22, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0456] MS[M+H] + =690

[0457] Preparation Example 25. Synthesis of Compound E25

[0458] [Compound E25]

[0459]

[0460] The compound E25 was produced by the same method as in Production Example 1, except that 4-(2'-chloro-6'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-2-phenylquinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0461] MS[M+H] + =690

[0462] Preparation Example 26. Synthesis of Compound E26

[0463] [Compound E26]

[0464]

[0465] The compound E26 was produced by the same method as in Production Example 25, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0466] MS[M+H] + =690

[0467] Preparation Example 27. Synthesis of Compound E27

[0468] [Compound E27]

[0469]

[0470] The compound E27 was produced by the same method as in Production Example 25, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0471] MS[M+H] + =690

[0472] Preparation Example 28. Synthesis of Compound E28

[0473] [Compound E28]

[0474]

[0475] The compound E28 was produced by the same method as in Production Example 1, except that 4-(5'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-2-phenylquinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0476] MS[M+H] + =690

[0477] Preparation Example 29. Synthesis of Compound E29

[0478] [Compound E29]

[0479]

[0480] The compound E29 was produced by the same method as in Production Example 28, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0481] MS[M+H] + =690

[0482] Preparation Example 30. Synthesis of Compound E30

[0483] [Compound E30]

[0484]

[0485] The compound E30 was produced by the same method as in Production Example 28, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0486] MS[M+H] + =690

[0487] Preparation Example 31. Synthesis of Compound E31

[0488] [Compound E31]

[0489]

[0490] The compound E31 was produced by the same method as in Production Example 1, except that 4-(4'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-2-phenylquinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0491] MS[M+H] + =690

[0492] Preparation Example 32. Synthesis of Compound E32

[0493] [Compound E32]

[0494]

[0495] The compound E32 was prepared by the same method as in Preparation Example 31, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0496] MS[M+H] + =690

[0497] Preparation Example 33. Synthesis of Compound E33

[0498] [Compound E33]

[0499]

[0500] The compound E33 was prepared by the same method as in Preparation Example 31, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0501] MS[M+H] + =690

[0502] Preparation Example 34. Synthesis of Compound E34

[0503] [Compound E34]

[0504]

[0505] The compound E34 was produced by the same method as in Production Example 1, except that 4-(3'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-2-phenylquinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0506] MS[M+H] + =690

[0507] Preparation Example 35. Synthesis of Compound E35

[0508] [Compound E35]

[0509]

[0510] The compound E35 was prepared by the same method as in Preparation Example 34, except that (4-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0511] MS[M+H] + =690

[0512] Preparation Example 36. Synthesis of Compound E36

[0513] [Compound E36]

[0514]

[0515] The compound E36 was produced by the same method as in Production Example 34, except that (2-cyanophenyl)boronic acid was used instead of the compound (3-cyanophenyl)boronic acid.

[0516] MS[M+H] + =690

[0517] Preparation Example 37. Synthesis of Compound E37

[0518] [Compound E37]

[0519]

[0520] The compound E37 was produced by the same method as in Production Example 1, except that 4-(3'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-2-(naphthalene-2-yl)quinazoline was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0521] MS[M+H] + =740

[0522] Preparation Example 38. Synthesis of Compound E38

[0523] [Compound E38]

[0524]

[0525] The compound E38 was produced by the same method as in Production Example 1, except that 1-(5'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-2-ethyl-1H-benzo[d]imidazole was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0526] MS[M+H] + =630

[0527] Preparation Example 39. Synthesis of Compound E39

[0528] [Compound E39]

[0529]

[0530] The compound E39 was produced by the same method as in Production Example 1, except that 2-(4'-chloro-2'-(4,6-diphenyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-1-phenyl-1H-benzo[d]imidazole was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0531] MS[M+H] + =678

[0532] Preparation Example 40. Synthesis of Compound E40

[0533] [Compound E40]

[0534]

[0535] The compound E40 was produced by the same method as in Production Example 1, except that 2-(3'-(4,6-bis(phenyl-d5)-1,3,5-triazine-2-yl)-5-chloro-[1,1'-biphenyl]-2-yl-2',4',5',6'-d4)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0536] MS[M+H] + =731

[0537] Preparation Example 41. Synthesis of Compound E41

[0538] [Compound E41]

[0539]

[0540] The compound E41 was produced by the same method as in Production Example 1, except that 2-(4'-chloro-2'-(4,6-di-o-tolyl-1,3,5-triazine-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazineyl was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazineyl).

[0541] MS[M+H] + =745

[0542] Preparation Example 42. Synthesis of Compound E42

[0543] [Compound E42]

[0544]

[0545] The compound E42 was produced by the same method as in Production Example 1, except that 2-(2'-(4,6-bis(4-nitrophenyl)-1,3,5-triazine-2-yl)-5'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazineyl was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazineyl).

[0546] MS[M+H] + =807

[0547] If the production formulae described in the examples of this specification and the above intermediates are appropriately combined based on common technical knowledge, all the compounds of the above Chemical Formula 1 described in this specification can be produced.

[0548] Example 1-1

[0549] ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0550] On the ITO transparent electrode prepared as the anode, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio) and A hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 is deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The EB1 compound is vacuum-deposited to form an electron blocking layer. Next, a film having a thickness of The compound represented by the following chemical formula BH and the compound represented by the following chemical formula BD were vacuum deposited at a weight ratio of 50:1 to form a light-emitting layer. The compound represented by the following chemical formula HB1 was vacuum-deposited to form a hole blocking layer. Next, the compound ETL1 and the compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form a hole blocking layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by vapor deposition of a thickness of .

[0551]

[0552] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains Aluminum maintenance The evaporation speed is 2x10. -7 ~5ⅹ10 -6 A support is provided to produce an organic light-emitting device.

[0553] Example 1-2 to Example 1-42

[0554] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compound described in Table 1 below was used instead of the compound ETL1 in Example 1.

[0555] Comparative Examples 1-1 to 1-6

[0556] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compound described in Table 1 below was used instead of Compound ETL1. Compounds ET-1 to ET-6 used in Table 1 below are as follows.

[0557]

[0558] When current was applied to the organic light-emitting devices prepared by Examples 1-1 to 1-42 and Comparative Examples 1-1 to 1-6, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in [Table 1] T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[0559]

Table 1

[0560]

[0561]

[0562] As shown in Table 1, when an organic light-emitting device is manufactured by using the compound of the present invention as an electron injection and transport layer, excellent characteristics are exhibited in terms of efficiency, driving voltage and / or stability of the organic light-emitting device.

[0563] Compared with the commonly used electron injection and transport layers, when the position of the connecting group between the N-containing ring groups is shortened and the direction of the substituted connecting group is ortho and meta, thereby appropriately adjusting the conjugation, the characteristics as an electron injection and transport layer show low voltage, high efficiency and long life.

[0564] Comparative Example 1-1 used a compound in which the substituent bonded to the position adjacent to the triazine group was not a phenyl group but a carbazole group, and Comparative Examples 1-2 and 1-3 used compounds in which Ar1 was a five-membered ring and a four-membered ring, respectively.

[0565] They are different from the compounds of the present application in which a phenylene group is bonded to the position adjacent to the triazine group and a monocyclic or bicyclic N-containing heterocyclic group is contained in the meta position of the phenylene group. In addition, it can be confirmed that the experimental examples 1-1 to 1-42 using the compounds of the present application have low driving voltage, high efficiency, and significantly long life compared with the comparative examples 1-1 to 1-3.

[0566] Comparative Examples 1-4 to 1-6 are compounds containing no cyano group. It was confirmed that Examples 1-1 to 1-42 using the compounds of the present invention which necessarily contain one or more cyano groups have lower driving voltage, higher efficiency, and significantly longer life than Comparative Examples 1-4 to 1-6.

[0567] The above content describes the preferred embodiments of the present invention (electron injection and transport layer), but the present invention is not limited thereto and can be implemented in various forms within the scope of the protection required and the detailed description of the invention, which also belongs to the scope of the present invention.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In Chemical Formula 1, L is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, Ar is a substituted or unsubstituted monocyclic or bicyclic N-containing heteroaryl group, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a nitro group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, a and c are integers from 1 to 4, b is an integer from 1 to 3, d and e are integers from 1 to 5, When a is 2 or more, R1 are the same or different from each other. When b is 2 or more, R2 are the same or different from each other, When c is 2 or more, R3 are the same or different from each other. When d is 2 or more, R4 are the same or different from each other, When e is 2 or more, R5 are the same as or different from each other.

2. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-4: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] In the Chemical Formulas 1-1 to 1-4, R1 to R5, L, Ar, and a to e are the same as defined in the Chemical Formula 1.

3. The compound according to claim 1, wherein The chemical formula 1 is any one of the following chemical formulas 2-1 to 2-3: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] In the Chemical Formulas 2-1 to 2-3, R1 to R5, L, Ar, and a to e are the same as defined in the Chemical Formula 1.

4. The compound according to claim 1, wherein The L is a direct bond.

5. The compound according to claim 1, wherein The Ar is a substituted or unsubstituted monocyclic N-containing heteroaryl group.

6. The compound according to claim 1, wherein The Ar is a substituted or unsubstituted bicyclic N-containing heteroaryl group.

7. The compound according to claim 1, wherein The Ar is a N-containing monocyclic or bicyclic heteroaryl group substituted by an alkyl group or an aryl group.

8. The compound according to claim 1, wherein The chemical formula 1 is any one of the following structural formulas:

9. 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 8.

10. The organic light emitting device according to claim 9, wherein: The organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound.

11. The organic light emitting device according to claim 10, wherein: A light emitting layer is included between the electron injection layer, the electron transport layer, or the electron injection and transport layer and the anode.

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