Novel Compound and Organic Light-Emitting Device Using the Same

Abstract

The present invention provides a novel compound and an organic light-emitting device using the same.

Description

Technical Field

[0001] [Cross - Reference to Related Applications] This application claims the benefit of priority based on Korean Patent Application No. 10 - 2021 - 0023630 filed on February 22, 2021 and Korean Patent Application No. 10 - 2022 - 0022272 filed on February 21, 2022, and all the contents disclosed in the documents of the Korean patent applications are included as part of this specification.

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

Background Art

[0003] Generally, 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 have a wide viewing angle, excellent contrast, and fast response time, and many studies are being carried out on them due to their excellent luminance, driving voltage, and response speed characteristics.

[0004] An organic light - emitting device generally has a structure including a positive electrode, a negative electrode, and an organic layer between the positive electrode and the negative electrode. The organic layer often has a multilayer structure composed of different substances in order to improve the efficiency and safety of the organic light - emitting device. For example, it may consist of a hole injection layer, a hole transport layer, a light - emitting layer, an electron transport layer, an electron injection layer, etc. In such a structure of an organic light - emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the positive electrode and electrons are injected from the negative electrode. When the injected holes and electrons come into contact, an exciton is formed, and when this exciton falls back to the ground state again, light is emitted.

[0005] The development of new materials for the organic substances used in such organic light - emitting devices has been continuously required.

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

SUMMARY OF THE INVENTION

PROBLEMS TO BE SOLVED BY THE INVENTION

[0007] The present invention provides a novel compound and an organic light-emitting device containing the same.

MEANS FOR SOLVING THE PROBLEMS

[0008] The present invention provides a compound represented by the following Chemical Formula 1: [Chemical Formula 1]

Chem.

[0009] Also, the present invention provides an organic light-emitting device including a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound represented by Chemical Formula 1.

EFFECTS OF THE INVENTION

[0010] The compound represented by Chemical Formula 1 described above is used as a material for the organic layer of an organic light-emitting device, and can improve the efficiency, lower the driving voltage, and / or improve the lifetime characteristics in the organic light-emitting device.

Brief Description of the Drawings

[0011]

Figure 1

Figure 2

Embodiments for Carrying Out the Invention

[0012] Hereinafter, it will be described in more detail to assist in understanding the present invention.

[0013] (Definition of Terms) In this specification,

Chem.

Chem.

[0014] As used herein, the term "substituted or unsubstituted" means deuterium; a halogen group; a cyano group; a nitro group; a hydroxy group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfinyl group; an arylsulfinyl group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl containing one or more of N, O, and S atoms, or two or more of the exemplified substituents are linked with a substituent Meaning substituted or unsubstituted. For example, the "substituent with two or more substituents linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group and may also be interpreted as a substituent with two phenyl groups linked. As an example, the term "substituted or unsubstituted" may be interpreted to mean "unsubstituted or substituted with one or more, for example, 1 to 5 substituents selected from the group consisting of deuterium, halogen, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms". Also, as used herein, the term "substituted with one or more substituents" may be interpreted to mean, for example, "substituted with 1 to 5 substituents" or "substituted with 1 or 2 substituents".

[0015] In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, compounds having the following structures may be used, but are not limited thereto.

Chemical formula

[0016] In this specification, the ester group may be substituted such that the oxygen of the ester group is a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound represented by the following structural formula, but is not limited thereto.

Chem.

[0017] In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, it may be a substituent having the following structure, but is not limited thereto.

Chem.

[0018] In this specification, examples of the silyl group specifically include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but are not limited thereto.

[0019] In this specification, examples of the boron group specifically include a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, etc., but are not limited thereto.

[0020] In this specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0021] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably from 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is from 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is from 1 to 10. According to yet another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, etc., but are not limited thereto.

[0022] In this specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0023] In this specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms is preferably 3 to 60. According to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0024] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, etc.

[0025] In this specification, the heteroaryl is a heteroaryl containing one or more of O, N, Si, and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of heteroaryl include, but are not limited to, a thiophene group, a furanyl group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group.

[0026] In this specification, for the aryl group in an aralkyl group, an aralkenyl group, an alkylaryl group, an arylamine group, or an arylsilyl group, the description of the aryl group as described above is applicable. In this specification, for the alkyl group in an aralkyl group, an alkylaryl group, or an alkylamine group, the description of the alkyl group as described above is applicable. In this specification, for the heteroaryl in a heteroarylamine, the description of the heteroaryl as described above is applicable. In this specification, for the alkenyl group in an aralkenyl group, the description of the alkenyl group as described above is applicable. In this specification, for an arylene, except that it is a divalent group, the description of the aryl group as described above is applicable. In this specification, for a heteroarylene, except that it is a divalent group, the description of the heteroaryl as described above is applicable. In this specification, for a hydrocarbon ring, except that it is not a monovalent group and is formed by bonding two substituents, the description of the aryl group or cycloalkyl group as described above is applicable. In this specification, for a heterocycle, except that it is not a monovalent group and is formed by bonding two substituents, the description of the heteroaryl as described above is applicable.

[0027] (Compound) On the other hand, the present invention provides a compound represented by the above chemical formula 1.

[0028] Specifically, the compound represented by the above chemical formula 1 has a dibenzofuran / dibenzothiophene core, and a phenyl group (phenyl-D5) substituted with 5 deuteriums at the 6-position of the core is substituted, and a triazinyl group is further substituted at the 3-position. Also, the compound may have a structure in which the carbon at the 8-position of the dibenzofuran / dibenzothiophene is unsubstituted or substituted with an aryl substituted with deuterium.

[0029] In particular, in the compound having a structure in which a triazinyl group is substituted at the 3-position of the dibenzofuran / dibenzothiophene core and a phenyl group substituted with 5 deuteriums is substituted at the 6-position, due to the characteristic that the bond energy of the C-D bond is greater than the bond energy of the C-H bond, compared with a compound having no phenyl group substituted with deuterium, it will have a stronger bond energy within the molecule, and thus can exhibit improved material stability. Further, since the compound is not directly substituted with deuterium in the dibenzofuran / dibenzothiophene core, it can exhibit high electronic stability compared with a compound directly substituted with deuterium in the core.

[0030] Therefore, the organic light-emitting device employing the compound has significantly improved lifetime characteristics.

[0031] In one embodiment, L, L1, and L2 can be a single bond, or an arylene having 6 to 20 carbon atoms that is unsubstituted or substituted with deuterium.

[0032] Specifically, L can be a single bond.

[0033] Further, L1 and L2 can each independently be a single bond or phenylene. In other words, L1 and L2 can each independently be a single bond, 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0034] For example, both L1 and L2 can be single bonds; or One of L1 and L2 can be a single bond, and the remaining one can be 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0035] At this time, L1 and L2 may be the same as each other. Or, L1 and L2 may be different.

[0036] Also, in one embodiment, Ar1 and Ar2 are each independently an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms; or a heteroaryl group having 2 to 60 carbon atoms which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, alkyl having 1 to 10 carbon atoms, and aryl having 6 to 20 carbon atoms and containing one or more heteroatoms of N, O, and S.

[0037] Specifically, Ar1 and Ar2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, wherein Ar1 and Ar2 may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl, and phenyl.

[0038] More specifically, Ar1 and Ar2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, wherein Ar1 and Ar2 may be unsubstituted or substituted with 1 to 5 substituents selected from the group consisting of deuterium, methyl, and phenyl.

[0039] For example, Ar1 and Ar2 may each independently be any one selected from the group consisting of the following, but are not limited thereto:

Chemical formula

[0040] At this time, Ar1 and Ar2 may be the same as each other. Or, Ar1 and Ar2 may be different.

[0041] Also, in one embodiment, at least one of Ar1 and Ar2 can be an unsubstituted or deuterium-substituted aryl having 6 to 12 carbon atoms.

[0042] For example, at least one of Ar1 and Ar2 is

Chem.

Chem.

Chem.

Chem.

[0043] Also, in one embodiment, R can be hydrogen; or an unsubstituted or deuterium-substituted aryl having 6 to 20 carbon atoms.

[0044] More specifically, R can be hydrogen; unsubstituted or deuterium-substituted phenyl; unsubstituted or deuterium-substituted biphenylyl; or unsubstituted or deuterium-substituted naphthyl.

[0045] In other words, R can be hydrogen; unsubstituted or phenyl substituted with 1 to 5 deuteriums; unsubstituted or biphenylyl substituted with 1 to 9 deuteriums; or unsubstituted or naphthyl substituted with 1 to 7 deuteriums.

[0046] For example, R is hydrogen,

Chem.

Chem.

[0047] Also, in one embodiment, when R is not hydrogen, i.e., when R is an unsubstituted or deuterium-substituted aryl having 6 to 60 carbon atoms, R may be the same as Ar1 or Ar2.

[0048] Also, in one embodiment, the compound is represented by any one of the following 1-1 to 1- 5 : [Chemical Formula 1-1] [Chem.] [Chemical Formula 1-2] [Chem.] [Chemical Formula 1-3] [Chem.] [Chemical Formula 1-4] [Chem.] [Chemical Formula 1-5] [Chem.]

[0049] In Chemical Formulas 1-1 to 1-5, Y, L1, L2, Ar1, and Ar2 are as defined in Chemical Formula 1.

[0050] On the other hand, representative examples of the compound represented by Chemical Formula 1 are as follows: [Chem.] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry] [Chemistry]

[0051] On the one hand, the compound represented by the chemical formula 1 can be produced, for example, by a production method as shown in the following Reaction Formula 1: [Reaction Formula 1] [Chemistry]

[0052] In the Reaction Formula 1, X is a halogen, preferably bromine or chlorine, and the descriptions of the remaining substituents are as defined above.

[0053] Specifically, the compound represented by the chemical formula 1 can be produced by the Suzuki-coupling reaction of reactants A1 and A2. At this time, the Suzuki-coupling reaction is preferably carried out under a palladium catalyst and a base, and the reaction groups for the reaction can be changed by those known in the art. The production method will be further specified in the production examples described later.

[0054] (Organic Light-Emitting Device) On the other hand, the present invention provides an organic light-emitting device containing the compound represented by the chemical formula 1. As an example, the present invention provides an organic light-emitting device including a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound represented by the chemical formula 1.

[0055] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are laminated. 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 light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic layers.

[0056] In one embodiment, the organic layer may include a light-emitting layer, and at this time, the organic layer containing the compound may be the light-emitting layer.

[0057] In other embodiments, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at this time, the organic layer containing the compound may be the light-emitting layer or the electron transport layer.

[0058] In still other embodiments, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at this time, the organic layer containing the compound may be the light-emitting layer or the electron transport layer.

[0059] In still other embodiments, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and at this time, the organic layer containing the compound may be the light-emitting layer or the electron transport layer.

[0060] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer 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 further including a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and it may include fewer or more organic layers.

[0061] Also, the organic light-emitting device according to the present invention may be a normal-type organic light-emitting device having a structure in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate, where the first electrode is the positive electrode and the second electrode is the negative electrode. Also, the organic light-emitting device according to the present invention may be an inverted-type organic light-emitting device having a structure in which a negative electrode, one or more organic layers, and a positive electrode are sequentially stacked on a substrate, where the first electrode is the negative electrode and the second electrode is the positive electrode. For example, the structure of the organic light-emitting device according to an embodiment of the present invention is shown in FIGS. 1 and 2.

[0062] Figure 1 is a diagram showing an example of an organic light-emitting device including a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be included in the light-emitting layer.

[0063] Figure 2 is a diagram showing an example of an organic light-emitting device including a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 may be included in the light-emitting layer.

[0064] The organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers contain the compound represented by Chemical Formula 1. Further, when the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0065] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. At this time, a positive electrode is formed by depositing a metal, a metal oxide having conductivity, or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed thereon, and then a substance used as a negative electrode is deposited thereon for manufacturing. In addition to this method, an organic light-emitting device can be made by sequentially depositing an organic layer and a positive electrode material from a negative electrode material on a substrate.

[0066] In addition, the compound represented by Chemical Formula 1 can be formed in the organic layer not only by vacuum evaporation but also by solution coating during the production of the organic light-emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0067] In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing an organic layer and a positive electrode material from a negative electrode material on a substrate (WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0068] As an example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0069] As the positive electrode material, a material having a large work function is preferably used so that hole injection into the organic layer is smooth. Specific examples of the positive electrode material 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.

[0070] As the negative electrode material, a material having a small work function is preferably used so that electron injection into the organic layer is easy. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structured materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0071] Also, the hole injection layer is a layer that injects holes from the electrode. As the hole injection material, a compound having the ability to transport holes, excellent hole injection effects from the positive electrode and to the light-emitting layer or light-emitting material, preventing the transfer of excitons generated in the light-emitting layer to the electron injection layer or electron injection material, and having excellent thin film forming ability is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, and conductive polymers such as polyaniline and polythiophene, but are not limited thereto.

[0072] Also, the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As the hole transport material, a material that can receive hole transport from the positive electrode or the hole injection layer and transfer it to the light-emitting layer, and a material having a large mobility with respect to holes is suitable. As the hole transport material, arylamine-based organic substances, conductive polymers, and block copolymers in which both a conjugated part and a non-conjugated part are present can be used, but are not limited thereto.

[0073] Also, the electron blocking layer is formed on the hole transport layer, preferably provided in contact with the light-emitting layer, and means a layer that plays a role of improving the efficiency of the organic light-emitting device by adjusting the hole mobility, preventing excessive movement of electrons, and increasing the hole-electron coupling probability. The electron blocking layer contains an electron blocking material, and examples of such an electron blocking material include arylamine-based organic substances, but are not limited thereto.

[0074] Further, the light-emitting layer may include a host material and a dopant material. As such a dopant material, the compound represented by the chemical formula 1 can be used. Further, as the host material, in addition to the compound represented by the chemical formula 1, a condensed aromatic ring derivative or a heterocyclic compound can be further included. Specifically, examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0075] In one embodiment, the light-emitting layer may further include, in addition to the compound represented by the chemical formula 1, a compound represented by the following chemical formula 2: [Chemical formula 2]

Chemical formula

[0076] When the organic light-emitting device further includes the compound represented by the chemical formula 2 capable of efficiently transferring holes from the host material of the light-emitting layer to the dopant material, the probability of recombination of holes and electrons in the light-emitting layer becomes high together with the compound represented by the chemical formula 1 having excellent electron transport ability, and the efficiency and lifetime of the organic light-emitting device can be improved.

[0077] According to one embodiment, the compound represented by Chemical Formula 2 is represented by the following Chemical Formula 2': [Chemical Formula 2'] [Chem.] In Chemical Formula 2', Ar'1, Ar'2, R'1, R'2, r, and s are as defined in Chemical Formula 2 above.

[0078] In Chemical Formula 2, Ar'1 and Ar'2 are each independently an aryl having 6 to 20 carbon atoms, or a heteroaryl having 2 to 20 carbon atoms containing 1 heteroatom among N, O, and S, wherein Ar'1 is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and aryl having 6 to 20 carbon atoms.

[0079] For example, Ar'1 and Ar'2 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl, wherein Ar'1 is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and aryl having 6 to 20 carbon atoms.

[0080] At this time, at least one of Ar'1 and Ar'2 may be phenyl or biphenylyl.

[0081] In Chemical Formula 2, R'1 and R'2 may each independently be hydrogen, deuterium, or aryl having 6 to 20 carbon atoms.

[0082] For example, R'1 and R'2 may each independently be hydrogen, deuterium, or phenyl, but are not limited thereto.

[0083] Also, r and s, which respectively indicate the number of R'1 and R'2, are each independently 0, 1, 2, 3, 4, 5, 6, or 7.

[0084] More specifically, r and s are each independently 0, 1, or 7.

[0085] For example, r + s is 0 or 1.

[0086] Typical examples of the compound represented by Chemical Formula 2 are as follows:

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[0087] The compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, which are such two host substances, are contained in the light-emitting layer at a weight ratio of 10:90 to 90:10, and as an example, at a weight ratio of 50:50.

[0088] In addition, examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, examples of the aromatic amine derivative include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamino group. Examples of the styrylamine compound include compounds in which at least one arylvinyl group is substituted for a substituted or unsubstituted arylamine, and the substituent is substituted or unsubstituted with one or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., but not limited thereto. Examples of the metal complex include iridium complexes, platinum complexes, etc., but not limited thereto.

[0089] In addition, the hole blocking layer is formed on the light emitting layer, preferably provided in contact with the light emitting layer, and means a layer that plays a role of improving the efficiency of the organic light emitting device by adjusting the electron mobility, preventing excessive movement of holes, and increasing the binding probability between holes and electrons. The hole blocking layer contains a hole blocking substance, and examples of such a hole blocking substance include azine derivatives containing triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; compounds into which an electron-withdrawing group such as a phosphine oxide derivative is introduced, but are not limited thereto.

[0090] In addition, the electron transport layer serves to transport electrons received from the electron injection layer to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. The electron transport layer contains an electron transport material, and as such an electron transport material, a material with high mobility for electrons is preferable. Specific examples of the electron transport material include an Al complex of 8-hydroxyquinoline; a complex containing Alq3; an organic radical compound; a hydroxyflavone-metal complex; a triazine derivative, etc., but are not limited thereto. Alternatively, these can be used together with electron transport materials such as fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, etc. and their derivatives, metal complex compounds, or nitrogen-containing 5-membered ring derivatives, etc.

[0091] In addition, the electron injection layer serves to inject electrons from the electrode, and is formed on the electron transport layer. As the electron injection material contained in the electron injection layer, LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, etc. can be used, but are not limited thereto.

[0092] Here, examples of the metal complex compound include, but are not limited to, lithium 8-hydroxyquinolinate, zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), chlorogallium bis(2-methyl-8-hydroxyquinolinate), (o-cresolate)gallium bis(2-methyl-8-hydroxyquinolinate), aluminum bis(2-methyl-8-hydroxyquinolinate)(1-naphtholate), gallium bis(2-methyl-8-hydroxyquinolinate)(2-naphtholate).

[0093] The organic light-emitting device according to the present invention can be a bottom emission element, a top emission element, or a double-sided emission element, and in particular, can be a bottom emission element that requires relatively high luminous efficiency.

[0094] In addition, the compound represented by Chemical Formula 1 can be included in an organic solar cell or an organic transistor in addition to the organic light-emitting device.

[0095] Hereinafter, the production of the compound represented by Chemical Formula 1 and the organic light-emitting device containing the same will be specifically described by way of examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereby.

[0096] [Production Example] Production Example 1: Production of Compound A-4 1) Production of Compound A-1 [Chemical Formula] Under a nitrogen atmosphere, 2-bromo-6-iodophenol (50 g, 178.6 mmol) and (4-chloro-2-fluorophenyl)boronic acid (31.1 g, 178.6 mmol) were placed in 1000 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (74.1 g, 535.8 mmol) was dissolved in 74 mL of water and added, and after sufficient stirring, tetrakistriphenylphosphine-palladium (6.2 g, 5.4 mmol) was added. After reacting for 2 hours, it was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again put into 1071 mL of chloroform and dissolved, washed twice with water, then the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce a gray solid compound A-1 (35.4 g, 66%, MS: [M+H] + =300.9).

[0097] 2) Preparation of compound A-2

Chemical formula

[0098] 3) Preparation of compound A-3

Chemical formula

[0099] 4) Production of Compound A-4

Chemical formula

[0100] Production Example 2: Production of Compound B-4 1) Production of Compound B-2 [Chemical formula] Under a nitrogen atmosphere, A-1 (50 g, 166.7 mmol) and phenylboronic acid-D5 (21.2 g, 166.7 mmol) were placed in 1000 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (69.1 g, 500.1 mmol) was dissolved in 69 mL of water and added, and after sufficient stirring, tetrakis triphenyl-phosphinopalladium (5.8 g, 5 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, then the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was put back into 1011 mL of chloroform and dissolved, washed twice with water, then the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce a yellow solid compound B-2 (38.4 g, 76%, MS: [M+H] + = 304.1).

[0101] 2) Production of compound B-3 [Chemical formula] Under a nitrogen atmosphere, B-2 (50 g, 165 mmol) and N-Bromosuccinimide (32.3 g, 181.5 mmol) were placed in 250 mL of dimethylformamide and reacted for 3 hours, then water was added while cooling in an ice bath. Then, the formed solid was filtered. This was put back into 596 mL of chloroform and dissolved, washed twice with water, then the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica column using chloroform and ethyl acetate to produce a white solid compound B-3 (39.9 g, 67%, MS: [M+H] + = 362).

[0102] 2) Production of compound B-4 [Chemical formula] Under a nitrogen atmosphere, B-3 (50 g, 131.2 mmol) was placed in 250 mL of dimethylformamide, potassium carbonate was added, and then the mixture was stirred and heated at 140 °C. After reacting for 7 hours, it was cooled to room temperature, and then water was added. Thereafter, the formed solid was filtered. This was again put into 474 mL of chloroform to dissolve it, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica column using chloroform and ethyl acetate to obtain a white solid compound B-4 (31.3 g, 66%, MS: [M+H] + = 362).

[0103] Production Example 3: Production of Compound C-1 1) Production of Compound C-1

Chemical formula

[0104] 2) Production of Compound C-2

Chemical formula

[0105] Production Example 4: Production of Compound D-1 1) Production of Compound D-1

Chemical Structure

[0106] 2) Production of Compound D-2 [Chemistry] Under a nitrogen atmosphere, D-1 (50 g, 139.2 mmol) and bis(pinacolato)diboron (38.9 g, 153.2 mmol) were placed in 1000 mL of 1,4-dioxane and stirred and refluxed. Then, potassium acetate (40.1 g, 417.7 mmol) was added and stirred thoroughly, and then dibenzylideneacetone palladium (2.4 g, 4.2 mmol) and tricyclohexylphosphine (2.3 g, 8.4 mmol) were added. After reacting for 3 hours, it was cooled to room temperature, the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in 635 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound D-2 (42.6 g, 67%, MS: [M+H] + = 457.2).

[0107] Production Example 5: Production of Compound E-1 1) Production of Compound E-1 [Chemistry] Under a nitrogen atmosphere, B-4 (50 g, 138.5 mmol) and [1,1'-biphenyl]-4-ylboronic acid (27.4 g, 138.5 mmol) were placed in 1000 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (57.4 g, 415.5 mmol) was dissolved in 57 mL of water and added and stirred thoroughly, and then tetrakis(triphenylphosphine)palladium (4.8 g, 4.2 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and then the organic layer was distilled. This was again dissolved in 1205 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E-1 (32.5 g, 54%, MS: [M+H]+ = 436.1).

[0108] 2) Preparation of Compound E-2 [Chemical formula] Under a nitrogen atmosphere, E-1 (50 g, 114.9 mmol) and bis(pinacolato)diboron (32.1 g, 126.4 mmol) were placed in 1000 mL of 1,4-dioxane and stirred and refluxed. Then, potassium acetate (33.1 g, 344.7 mmol) was added and stirred well, followed by the addition of dibenzylideneacetone palladium (2 g, 3.4 mmol) and tricyclohexylphosphine (1.9 g, 6.9 mmol). After reacting for 5 hours and cooling to room temperature, the organic layer was filtered to remove salts, and then the filtered organic layer was distilled. This was again dissolved in 606 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound E-2 (43 g, 71%, MS: [M+H] + = 528.3).

[0109] Production Example 6: Preparation of Compound F-1 1) Preparation of Compound F-1 [Chemical formula] Under a nitrogen atmosphere, B-4 (50 g, 138.5 mmol) and naphthalene-2-ylboronic acid (23.8 g, 138.5 mmol) were placed in 1000 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (57.4 g, 415.5 mmol) was dissolved in 57 mL of water and added and stirred well, followed by the addition of tetrakis(triphenylphosphine)palladium (4.8 g, 4.2 mmol). After reacting for 2 hours and cooling to room temperature, the organic layer and the aqueous layer were separated, and then the organic layer was distilled. This was again dissolved in 1133 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound F-1 (43.6 g, 77%, MS: [M+H] +=(410.1) was produced.

[0110] 2) Production of Compound F-2

Chem.

[0111] Production Example 7: Production of Compound G-2 1) Production of Compound G-1

Chem.

[0112] 2) Production of compound G-2

Chemical formula

[0113] Synthesis example 1: Production of compound 1 [Chemistry] Under a nitrogen atmosphere, A-4 (20 g, 53.3 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (14.2 g, 53.3 mmol) were placed in 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 3 hours, it was cooled to room temperature, and the resulting solid was filtered. The solid was put into 1280 mL of chloroform and dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce a white solid compound Compound1 (18.2 g, 71%, MS: [M+H] + = 481.2).

[0114] Synthesis Example 2: Production of Compound 2 [Chemistry] Under a nitrogen atmosphere, A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) were placed in 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 2 hours, it was cooled to room temperature, and the resulting solid was filtered. The solid was put into 1482 mL of chloroform and dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce a white solid compound Compound2 (17.8 g, 60%, MS: [M+H] + = 557.2).

[0115] Synthesis Example 3: Production of Compound 3

Chem.

[0116] Synthesis Example 4: Production of Compound 4

Chem.

[0117] Synthesis Example 5: Production of Compound 5

Chemical Structure

[0118] Synthesis Example 6: Preparation of Compound 6

Chem.

[0119] Synthesis Example 7: Preparation of Compound 7

Chem.

[0120] Synthesis Example 8: Production of Compound 8

Chemical Structure

[0121] Synthesis Example 9: Production of Compound 9

Chemical Structure

[0122] Synthesis Example 10: Preparation of Compound 10

Chemical formula

[0123] Synthesis Example 11: Preparation of Compound 11 [Chemical formula] Under a nitrogen atmosphere, D-2 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) were placed in 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 3 hours and cooling to room temperature, the resulting solid was filtered. The solid was added to 1698 mL of chloroform and dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound Compound11 (20.4 g, 60%, MS: [M+H] + = 638.3).

[0124] Synthesis Example 12: Production of Compound 12 [Chemical formula] Under a nitrogen atmosphere D-2 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) were placed in 400 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (22.1 g, 159.9 mmol) was dissolved in 22 mL of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 1 hour and cooling to room temperature, the resulting solid was filtered. The solid was added to 1736 mL of chloroform and dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound Compound12 (24.6 g, 71%, MS: [M+H] +=(652.3) was produced.

[0125] Synthesis Example 13: Production of Compound 13

Chemical formula

[0126] Synthesis Example 14: Production of Compound 14

Chemical formula

[0127] Synthesis Example 15: Preparation of Compound 15

Chemical Structure

[0128] Synthesis Example 16: Preparation of Compound 16

Chem.

[0129] Synthesis Example 17: Preparation of Compound 17

Chem.

[0130] Synthesis Example 18: Production of Compound 18

Chemical formula

[0131] Synthesis Example 19: Production of Compound 19

Chemical formula

[0132] Synthesis Example 20: Production of Compound 20

Chemical Structure

[0133] Example 1: Production of an Organic Light-Emitting Device A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,300 Å was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that had been secondarily filtered through a filter of a product manufactured by Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each. After the distilled water cleaning was completed, ultrasonic cleaning was performed with solvents of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaning device. Further, after cleaning the substrate with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporation device.

[0134] On the thus-prepared ITO transparent electrode, the following HI-1 compound was thermally vacuum-evaporated to a thickness of 50 Å to form a hole injection layer. On the hole injection layer, the following HT-1 compound was thermally vacuum-evaporated to a thickness of 250 Å to form a hole transport layer, and on the HT-1 evaporation film, the following HT-2 compound was vacuum-evaporated to a thickness of 50 Å to form an electron blocking layer.

[0135] On the HT-2 evaporation film, as the light-emitting layer, Compound 1 manufactured in Synthesis Example 1, the following YGH-1 compound, and the phosphorescent dopant YGD-1 were co-evaporated at a weight ratio of 44:44:12 to form a light-emitting layer with a thickness of 400 Å.

[0136] On the light-emitting layer, the following ET-1 compound was vacuum-evaporated to a thickness of 250 Å to form an electron transport layer, and on the electron transport layer, the following ET-2 compound and LiF were vacuum-evaporated at a weight ratio of 98:2 to form an electron injection layer with a thickness of 100 Å. On the electron injection layer, aluminum was evaporated to a thickness of 1,000 Å to form a negative electrode.

Chemical formula

[0137] In the above process, the evaporation rate of the organic matter was maintained at 0.4 to 0.7 Å / sec, aluminum was maintained at an evaporation rate of 2 Å / sec, and the degree of vacuum during evaporation was 1×10 -7~5×10 -8 was maintained at torr.

[0138] Examples 2 to 20 An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of Compound 1 of Synthesis Example 1 as one of the host materials of the light-emitting layer in Example 1.

[0139] At this time, when the structures of the compounds used in Examples 1 to 20 are arranged, they are as follows.

Chemical formula

Chemical formula

[0140] Comparative Examples 1 to 5 An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 below was used instead of Compound 1 of Synthesis Example 1 as one of the host materials of the light-emitting layer in Example 1. At this time, the compounds of CE1 to CE5 in Table 1 below are as follows.

Chemical formula

[0141] Experimental Example 1: Evaluation of device characteristics For each of the organic light-emitting devices manufactured in the above Examples and Comparative Examples, the voltage and efficiency at a current density of 10 mA / cm 2 were measured, and the lifetime at a current density of 50 mA / cm 2 was measured, and the results are shown in Table 1 below. At this time, LT95 means the time until the initial luminance decreases to 95%.

Table 1

[0142] As shown in Table 1 above, it was found that the organic light-emitting device of the example using the compound represented by Chemical Formula 1 as the host material of the light-emitting layer showed significantly improved lifetime characteristics without a decrease in efficiency compared to the organic light-emitting device of the comparative example using a compound having a different structure. Therefore, considering that the luminous efficiency and lifetime characteristics of organic light-emitting devices generally have a trade-off relationship with each other, it was confirmed that the compound of the present invention can improve the characteristics of organic light-emitting devices compared to the comparative compound.

Explanation of Reference Signs

[0143] 1 Substrate 2 Anode 3 Light-emitting layer 4 Cathode 5 Hole injection layer 6 Hole transport layer 7 Electron blocking layer 8 Electron transport layer 9 Electron injection layer

Claims

1. A compound represented by the following Chemical Formula 1: [Chemical Formula 1] 【Chemical Formula 1】 In the Chemical Formula 1, Y is O or S, D means deuterium, L is a single bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms, L １ is a single bond; or an arylene having 6 to 60 carbon atoms that is substituted or unsubstituted, Ar １ is a substituted or unsubstituted aryl having 6 to 60 carbon atoms, L ２ is a single bond, Ar ２ is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from N, O, and S, R is hydrogen; or an aryl having 6 to 60 carbon atoms which is unsubstituted or substituted with deuterium, The term "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, an alkyl group, and an aryl group, or being substituted or unsubstituted with a substituent in which two or more of the exemplified substituents are linked.

2. The compound according to Claim 1, wherein L is a single bond.

3. L １ The compound according to claim 1, wherein L is a single bond or phenylene.

4. Ar １ is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, or fluorenyl, and Ar ２ is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, and Here, Ar １ and Ar ２ is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, methyl, and phenyl, the compound according to claim 1.

5. Ar1 is any one selected from the group consisting of the following: [Chemical] Ar ２ is any one selected from the group consisting of the following: the compound according to claim 4: [Chemical 2] 。

6. Ar １ and Ar ２ The compound according to claim 1, wherein at least one of them is unsubstituted or an aryl having 6 to 12 carbon atoms substituted with deuterium.

7. The compound according to Claim 1, wherein R is hydrogen; phenyl which is unsubstituted or substituted with deuterium; biphenylyl which is unsubstituted or substituted with deuterium; or naphthyl which is unsubstituted or substituted with deuterium.

8. R is hydrogen, [Chemical Formula 3] 、 【Chemical Formula 4】 、 【Chemical Formula 5】 or 【Chemical Formula 6】 The compound according to Claim 7.

9. The compound according to Claim 1, wherein the compound is represented by any one of the following Chemical Formulas 1-1 to 1-5: [Chemical Formula 1-1] 【Chemical Formula 7】 [Chemical Formula 1-2] 【Chemical Formula 8】 [Chemical Formula 1-3] 【Chemical Formula 9】 [Chemical Formula 1-4] 【Chemical Formula 10】 [Chemical Formula 1-5] 【Chemical 11】 In the Chemical Formulas 1-1 to 1-5, Y, L １ , L ２ , Ar １ and Ar ２ are as defined in claim 1.

10. The compound according to Claim 1, wherein the compound is any one selected from the group consisting of the following compounds: 【Chemical 12】 【Chemical 13】 【Chemical Formula 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical Formula 18】 【Chemical 19】 【Chemical 20】 【Chemical 21】 【Chemical 22】 【Chemical 23】 【Chemical Formula 24】 [Chemical Formula 25] 【Chemical 26】 【Chemical 27】 [Chemical Formula 28] 【Chemical 29】 【Chemical 30】 【Chemical 31】 。

11. An organic light-emitting device including a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain 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 containing the compound is a light-emitting layer.

13. The organic light-emitting device according to Claim 12, wherein the light-emitting layer further contains a compound represented by the following Chemical Formula 2: [Chemical Formula 2] 【Chemical 32】 In the Chemical Formula 2, Ar' １ and Ar' ２ each independently is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from N, O and S, which may be substituted or unsubstituted, R' １ and R' ２ are each independently hydrogen; deuterium; or aryl having 6 to 20 carbon atoms, r and s are each independently an integer from 0 to 7, The term "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; an alkyl group; and an aryl group, or substituted or unsubstituted with a substituent in which two or more of the exemplified substituents are linked.

14. The organic light-emitting device according to claim 13, wherein the compound represented by Chemical Formula 2 is any one selected from the group consisting of the following compounds: 【Chemical 33】 【Chemical 34】 【Chemical 35】 【Chemical 36】 【Chemical 37】 【Chemical 38】 【Chemical Formula 39】 【Chemical Formula 40】 。

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