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, the compound of Chemical Formula 1 being used in an organic light-emitting device, which can reduce a driving voltage of the organic light-emitting device, can improve light efficiency, and can improve lifespan characteristics of the device using thermal stability of the compound.

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0040683 filed with the Korean Patent Office on March 28, 2023, the entire contents of which are incorporated into this specification.

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

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting 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 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.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above. Summary of the invention

[0005] Technical issues

[0006] The present specification provides a compound and an organic light-emitting device including the same.

[0007] Solution to the problem

[0008] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0009] [Chemical formula 1]

[0010]

[0011] In the above chemical formula 1,

[0012] R1 to R 10 Any one of them is a part that binds to L1, and the others are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0013] L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0014] Ar1 is substituted or unsubstituted benzo substituted or unsubstituted dibenzo base,

[0015] x is 1 or 2,

[0016] m is 0 to 3. When m is 2 or more, two or more L1 are the same or different from each other.

[0017] y is 1 or 2. When y is 2, two Ar1s are the same as or different from each other.

[0018] In addition, another embodiment of the present specification provides an organic light-emitting device, comprising:

[0019] a first electrode; a second electrode; and one or more organic layers disposed between the first electrode and the second electrode,

[0020] At least one of the organic layers contains the compound of Chemical Formula 1.

[0021] In addition, another embodiment of the present specification provides an organic light-emitting device, comprising:

[0022] an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer,

[0023] The first light-emitting layer comprises the compound of the chemical formula 1,

[0024] The second light-emitting layer includes at least one of the compound of the following Chemical Formula 2 and the compound of the following Chemical Formula 3.

[0025] [Chemical formula 2]

[0026]

[0027] In the above chemical formula 2,

[0028] At least one of R11 to R20 is bonded to the * site of the following chemical formula 2-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group,

[0029] [Chemical formula 2-1]

[0030]

[0031] L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0032] Ar2 is a substituted or unsubstituted aryl group,

[0033] p is an integer from 1 to 3,

[0034] [Chemical formula 3]

[0035]

[0036] In the above chemical formula 3,

[0037] At least one of Y1 to Y10 is bonded to the * site of the following chemical formula 3-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group,

[0038] [Chemical formula 3-1]

[0039]

[0040] A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle,

[0041] L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0042] q is an integer from 1 to 3.

[0043] Effects of the Invention

[0044] The compound according to one embodiment of the present specification is used in an organic light-emitting device, which can reduce the driving voltage of the organic light-emitting device and improve the light efficiency. In addition, the thermal stability of the compound can be used to improve the life characteristics of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0045] Figure 1 An example of an organic light-emitting device according to an embodiment of the present specification is illustrated.

[0046] Figure 2 An example of an organic light-emitting device according to an embodiment of the present specification is illustrated.

[0047] Figure 3 An example of an organic light-emitting device according to an embodiment of the present specification is illustrated.

[0048] Figure 4 This is the MS chart of compound A.

[0049] Figure 5 This is a graph showing the results of HPLC analysis of a film deposited from the mixture of Production Example 3.

[0050] Figure 6 This is a diagram showing the results of HPLC analysis of a film deposited from the mixture of Production Example 4.

[0051] [Explanation of symbols]

[0052] 1: Substrate

[0053] 2: First electrode

[0054] 3: Second electrode

[0055] 4: Luminous layer

[0056] 4-1: The first light-emitting layer

[0057] 4-2: Second light-emitting layer

[0058] 5: Hole injection layer

[0059] 6: Hole transport layer

[0060] 7: Hole regulation layer

[0061] 8: Electronic adjustment layer

[0062] 9: Electron transport layer

[0063] 10: Electron injection layer

[0064] 11: Overlay DETAILED DESCRIPTION

[0065] Next, this specification is described in more detail.

[0066] One embodiment of the present specification provides the compound of the above Chemical Formula 1.

[0067] According to the chemical formula 1 of one embodiment of the present specification, in the benzo[ghi]fluoranthene structure, Ar1 as a specific functional group is combined through L1 as an intermediate connecting group, and the electron transfer and hole transfer capabilities are excellent, and the quantum efficiency is high. Therefore, the compound of the above chemical formula 1 is applied to the organic layer of the organic light-emitting device, and the effects of reducing the driving voltage, improving the efficiency and prolonging the life can be seen.

[0068] Throughout the present specification, the term "combination thereof" included in the expression of Markush form means a mixture or combination of one or more components selected from the expression of Markush form, and means that one or more components selected from the above components are included.

[0069] In the present specification, examples of substituents are described below, but are not limited thereto.

[0070] In this manual, Indicates the connected part.

[0071] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a 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.

[0072] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, an aryloxy group, an alkylthio group, Arylthio The group may be substituted with one or more substituents selected from the group consisting of alkenyl, haloalkyl, haloalkoxy, arylalkyl, silyl, boron, amine, aryl, condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and heterocyclic group, or may be substituted with a substituent formed by connecting two or more of the substituents listed above, or may not have any substituent.

[0073] In this specification, two or more substituents are linked to each other, which means that the hydrogen of any substituent is linked to another substituent. For example, two substituents can be linked to each other to form a phenyl group and a naphthyl group. In addition, the three substituents connected include not only (substituent 1)-(substituent 2)-(substituent 3) connected continuously, but also (substituent 2) and (substituent 3) connected to (substituent 1). For example, phenyl, naphthyl and isopropyl can be connected to form The above definition also applies to 4 or more substituents connected together.

[0074] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0075] 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 30. Specific examples 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, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0076] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, and specifically includes 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, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, and norbornyl, but is not limited thereto.

[0077] In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 30. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0078] In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0079] In the present specification, the above-mentioned halogenated alkyl group refers to an alkyl group in the definition of the above-mentioned alkyl group substituted with at least one halogen group.

[0080] In the present specification, the above-mentioned halogenated alkoxy group means that at least one halogen group is substituted in place of the hydrogen of the alkoxy group in the definition of the above-mentioned alkoxy group.

[0081] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

[0082] When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0083] When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, phenanthrenyl, perylene, yl, fluorenyl, etc., but are not limited to these.

[0084] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0085] When the above fluorenyl group is substituted or forms a ring,

[0086]

[0087] etc., but not limited thereto.

[0088] In this specification, "adjacent" groups may refer to substituents substituted on atoms directly connected to the atom substituted by the substituent, substituents closest to the substituent in stereostructure, or other substituents substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0089] In the present specification, an arylalkyl group means that the above-mentioned alkyl group is substituted with an aryl group, and the aryl group and the alkyl group of the above-mentioned arylalkyl group can be the same as those exemplified above for the aryl group and the alkyl group.

[0090] In the present specification, the aryloxy group means that the alkyl group of the alkoxy group in the definition of the above-mentioned alkoxy group is replaced by an aryl group. Examples of the aryloxy group include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthranyloxy, 3-phenanthranyloxy, and 9-phenanthranyloxy, but are not limited thereto.

[0091] In the present specification, the alkyl group of the alkylthio group is the same as the examples of the alkyl group described above. Specifically, examples of the alkylthio group include, but are not limited to, a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and the like.

[0092] In the present specification, the aryl group in the arylthio group is the same as the examples of the aryl group described above. Specifically, examples of the arylthio group include phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, and the like, but are not limited thereto.

[0093] In the present specification, the heterocyclic group contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc., including aromatic heterocyclic groups or aliphatic heterocyclic groups. The aromatic heterocyclic group may be represented by a heteroaryl group. The number of carbon atoms in the heterocyclic group is not particularly limited, but preferably the number of carbon atoms is 2 to 30. The heterocyclic group may be a monocyclic or polycyclic group. Examples of heterocyclic groups include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthridine, phenanthroline, isothiophene Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothioyl, phenanthroline Thiazole (phenoxathiine), phen The present invention also includes, but is not limited to, phenoxazine, phenothiazine, decahydrobenzocarbazolyl, hexahydrocarbazolyl, dihydrobenzoazasilyl, dihydroindenocarbazolyl, spirofluorenylxanthenyl, spirofluorenylthioxanthenyl, tetrahydronaphthothienyl, tetrahydronaphthofuranyl, tetrahydrobenzothienyl and tetrahydrobenzofuranyl.

[0094] In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, a heteroarylsilyl group, etc. The alkyl group in the alkylsilyl group may be the same as the examples given above for the alkyl group, the aryl group in the arylsilyl group may be the same as the examples given above for the aryl group, the alkyl group and the aryl group in the alkylarylsilyl group may be the same as the examples given above for the alkyl group and the aryl group, and the heteroaryl group in the heteroarylsilyl group may be the same as the examples given above for the heterocyclic group.

[0095] In this specification, the boron group can be -BY 100 Y 101 , the above Y 100 and Y 101 The same or different, each independently can be selected from hydrogen, deuterium, halogen, nitrile, substituted or unsubstituted monocyclic or polycyclic cycloalkyl having 3 to 30 carbon atoms, substituted or unsubstituted linear or branched alkyl having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms. The above-mentioned boryl group specifically includes dimethylboryl, diethylboryl, tert-butylmethylboryl, diphenylboryl, etc., but is not limited thereto.

[0096] In the present specification, the amino group can be selected from -NH2, alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthracenylamino, 9-methyl-anthrylamino, diphenylamino, ditolylamino, N-phenyltolylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0097] 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 N of the amine group. The alkyl group and the aryl group in the above-mentioned N-alkylarylamine group are the same as the examples of the alkyl group and the aryl group described above.

[0098] 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 N of the amine group. The aryl group and the heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and the heterocyclic group described above.

[0099] 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 N of the amine group. The alkyl group and the heteroaryl group in the above-mentioned N-alkylheteroarylamine group are the same as the examples of the alkyl group and the heterocyclic group mentioned above.

[0100] In this specification, examples of alkylamino groups include substituted or unsubstituted monoalkylamino groups or substituted or unsubstituted dialkylamino groups. The alkyl group in the above-mentioned alkylamino groups may be a straight-chain or branched alkyl group. The alkylamino group containing two or more of the above-mentioned alkyl groups may contain a straight-chain alkyl group, a branched alkyl group, or may contain a straight-chain alkyl group and a branched alkyl group at the same time. For example, the alkyl group in the above-mentioned alkylamino group may be selected from the examples of the above-mentioned alkyl groups.

[0101] In this specification, examples of heteroarylamine groups include substituted or unsubstituted monoheteroarylamine groups, or substituted or unsubstituted diheteroarylamine groups. The heteroarylamine groups containing two or more of the above heteroaryl groups may contain monocyclic heteroaryl groups, polycyclic heteroaryl groups, or may contain both monocyclic heteroaryl groups and polycyclic heteroaryl groups. For example, the heteroaryl groups in the above heteroarylamine groups may be selected from the examples of the above heterocyclic groups.

[0102] In this specification, the alkyl group in N-alkylarylamine, alkylthio and N-alkylheteroarylamine is the same as the alkyl group exemplified above. Specifically, as the alkylthio, there are methylthio, ethylthio, tert-butylthio, hexylthio, octylthio, etc., but it is not limited thereto.

[0103] In the present specification, the aryl groups in the aryloxy group, arylthio group, N-arylalkylamine group and N-arylheteroarylamine group are the same as the examples of the aryl groups described above. Specifically, as the aryloxy group, there are phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-phenanthrenyl group, 3-phenanthrenyl group, 9-phenanthrenyl group, etc., and as the arylthio group, there are phenylthio group, 2-methylphenylthio group, 4-tert-butylphenylthio group, etc., but it is not limited thereto.

[0104] In the present specification, the hydrocarbon ring group can be an aromatic hydrocarbon ring group, an aliphatic hydrocarbon ring group, or a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and can be selected from the examples of the above-mentioned cycloalkyl group, aryl group, and combinations thereof. The above-mentioned hydrocarbon ring groups include phenyl, cyclohexyl, adamantyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.1]octyl, tetrahydronaphthyl, tetrahydroanthracenyl, 1,2,3,4-tetrahydro-1,4-methylenenaphthyl, 1,2,3,4-tetrahydro-1,4-ethylenenaphthyl, spirocyclopentanefluorenyl, spiroadamantanefluorenyl and spirocyclohexanefluorenyl, but are not limited thereto.

[0105] In the present specification, in the phrase “bonds with adjacent groups to form a ring”, “adjacent” has the same meaning as defined above, and the “ring” refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

[0106] 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 the above-mentioned monovalent group, may be selected from the above-mentioned cycloalkyl group, aryl group, and examples of combinations thereof, wherein 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, 1,2,3,4-tetrahydro-1,4-ethylenenaphthalene, spirocyclopentanefluorene, spiroadamantanefluorene, and spirocyclohexanefluorene, but are not limited thereto.

[0107] In the present specification, the heterocycle contains one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may contain one or more atoms selected from O, N, Se, S, etc. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic. The aromatic heterocycle may be selected from the examples of heteroaryl groups in the heterocyclic group except that it is not monovalent.

[0108] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, Examples of the present invention include, but are not limited to, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azacyclooctane, thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran.

[0109] In the present specification, examples of the aliphatic or aromatic / aliphatic condensed heterocyclic ring include tetrahydrobenzonaphthothiophene and tetrahydrobenzonaphthofuran, but are not limited thereto.

[0110] In the present specification, an arylene group refers to a group having two bonding positions on an aryl group, that is, a divalent group. The above description of the aryl group is applicable to these groups except that they are each a divalent group.

[0111] In the present specification, a divalent heterocyclic group refers to a group having two bonding positions on a heterocyclic group, that is, a divalent group. Except that each of them is a divalent group, the above description of the heterocyclic group is applicable.

[0112] Unless otherwise defined in this specification, all technical terms and scientific terms used in this specification have the same meaning as those generally understood by those skilled in the art. Methods and materials similar to or equivalent to the description in this specification can be used for the implementation or test of embodiments of the present invention, but suitable methods and materials are described later. All publications, patent applications, patents and other references mentioned in this specification are included in this specification as a whole as a reference, 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.

[0113] Next, the compound of the above Chemical Formula 1 will be described in detail.

[0114] According to one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formula 1-A.

[0115] [Chemical Formula 1-A]

[0116]

[0117] In the above chemical formula 1-A,

[0118] R1 to R 10 , L1, x, m and y are defined as in the above chemical formula 1,

[0119] R 101 To R 114 Any one of them is a portion that binds to L1, and the others are the same as or different from each other and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0120] According to one embodiment of the present specification, the above Chemical Formula 1 is the following Chemical Formula 1-B.

[0121] [Chemical Formula 1-B]

[0122]

[0123] In the above chemical formula 1-B,

[0124] R1 to R 10 , L1, x, m and y are defined as in the above chemical formula 1,

[0125] R 101 To R 116Any one of them is a portion that binds to L1, and the others are the same as or different from each other and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0126] According to one embodiment of the present specification, the above Chemical Formula 1 contains at least one deuterium.

[0127] According to one embodiment of the present specification, the above “comprising at least one deuterium” means that any one or more of the hydrogens at the substitutable positions are replaced by deuterium, or are replaced by a substituent substituted by deuterium. The above substituent includes the substituent defined in the above “substituted or unsubstituted”.

[0128] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 0.01% to 100%.

[0129] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 0.1% to 100%.

[0130] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 1% to 100%.

[0131] According to one embodiment of the present specification, the deuterium substitution rate of the above Chemical Formula 1 is 40% to 99%.

[0132] According to one embodiment of the present specification, when the above chemical formula 1 contains deuterium, it has the following effects. Specifically, the physical and chemical properties such as the bond length of the chemical bond related to deuterium are different from those of hydrogen. Compared with the CH bond, the stretching amplitude of the CD bond is smaller, so the van der Waals radius of deuterium is smaller than that of hydrogen. Generally, it can be shown that the CD bond is shorter and stronger than the CH bond. Therefore, when the hydrogen at the substitutable position of the above chemical formula 1 is replaced by deuterium, the energy of the ground state is reduced, and the bond length between deuterium and carbon becomes shorter, so the molecular hardcore volume is reduced, so the electrical polarizability can be reduced, and the intermolecular interaction is weakened, so that the film volume can be increased. In addition, such characteristics can produce the effect of reducing the crystallinity of the film, that is, the amorphous state, which can usually effectively improve the life and driving characteristics of the organic light-emitting device, and the heat resistance can be further improved compared with the existing organic light-emitting devices.

[0133] In the present specification, “containing deuterium”, “deuterated” or “deuterated” means that hydrogen at a substitutable position of the compound is substituted with deuterium.

[0134] In the present specification, “overdeuterated” refers to a compound or group in which all hydrogen in the molecule is replaced by deuterium, and has the same meaning as “100% deuterated”.

[0135] In the present specification, "X% deuterated", "deuteration degree X%" or "deuterium substitution rate X%" means that X% of the hydrogen atoms at substitutable positions in the structure are substituted with deuterium. For example, when the structure is dibenzofuran, "25% deuterated" the dibenzofuran, "deuteration degree 25%" of the dibenzofuran or "deuterium substitution rate 25%" of the dibenzofuran means that 2 of the 8 hydrogen atoms at substitutable positions of the dibenzofuran are substituted with deuterium.

[0136] In this specification, the "degree of deuteration" or "deuterium substitution rate" can be determined by nuclear magnetic resonance spectroscopy ( 1 The presence of the molecule can be confirmed by a known method such as HNMR (thin-layer chromatography / mass spectrometry), TLC / MS (thin-layer chromatography / mass spectrometry), or GC / MS (gas chromatography / mass spectrometry).

[0137] Specifically, by nuclear magnetic resonance spectroscopy ( 1 When analyzing the "deuteration degree" or "deuterium substitution rate" by H NMR, DMF (dimethylformamide) can be added as an internal standard. 1 The integration ratio on H NMR is used to calculate the degree of deuteration or deuterium substitution rate from the integrated amount of the total peak.

[0138] In addition, when analyzing the "degree of deuteration" or "deuterium substitution rate" by TLC / MS (thin layer chromatography / mass spectrometry), the substitution rate can be calculated based on the maximum value (median value) of the distribution formed by the molecular weight at the end of the reaction. For example, when analyzing the degree of deuteration of the following compound A, the molecular weight of the following starting material is 506. When it is indicated that Figure 4 When the maximum molecular weight (median value) of the following compound A in the MS chart is 527, 21 of the 26 hydrogen atoms at the substitutable positions of the following starting material are substituted with deuterium, and therefore it can be calculated that about 81% of the hydrogen atoms are deuterated.

[0139]

[0140] In this specification, D represents deuterium.

[0141] According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

[0142]

[0143]

[0144]

[0145]

[0146]

[0147] According to one embodiment of the present specification, the chemical formula 1 is any one selected from the following compounds.

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] According to one embodiment of the present specification, the band gap of the compound of Chemical Formula 1 is greater than or equal to 2.9 eV.

[0159] According to one embodiment of the present specification, the compound of Chemical Formula 1 has a band gap of 2.9 eV to 4.0 eV.

[0160] Specifically, the organic compound used in the organic light-emitting device must have a band gap of 0.5eV to 4.0eV to play the role of an organic semiconductor, and in order to display blue, a band gap energy of at least 2.9eV is required. According to the fluorescent blue light-emitting principle of the host-dopant system, the band gap of the blue fluorescent host must be greater than the band gap of the blue fluorescent dopant in order for energy transfer to occur smoothly. Therefore, the blue fluorescent host preferably has an energy band gap of 2.9eV to 4.0eV.

[0161] In this specification, "energy level" refers to the magnitude of energy. Therefore, the energy level is interpreted as representing the absolute value of the energy value. For example, the low or deep energy level means that the absolute value increases from the vacuum energy level to the negative direction.

[0162] In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital function (highest occupied molecular orbital) of the electron in the region with the highest energy in the region that can participate in the bonding, LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (lowest unoccupied molecular orbital) of the electron in the antibonding region with the lowest energy, and the HOMO energy level refers to the distance from the vacuum energy level to the HOMO. In addition, the LUMO energy level refers to the distance from the vacuum energy level to the LUMO.

[0163] In this specification, the HOMO level can be measured by using a photoelectron spectrometer (AC3 manufactured by Riken Keiki Co., Ltd.) under atmospheric pressure, and the LUMO level can be calculated using a wavelength value measured by photoluminescence (PL).

[0164] In this specification, the band gap refers to the difference between the HOMO energy level and the LUMO energy level.

[0165] The present specification provides an organic light-emitting device including the above-mentioned compound.

[0166] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0167] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0168] In this specification, the above-mentioned "layer" is interchangeable with the "film" mainly used in this technical field, and refers to a coating covering the target area. The size of the above-mentioned "layer" is not limited, and the sizes of each "layer" can be the same or different. According to one embodiment, the size of the "layer" can be equal to the size of the entire device, can be equivalent to the size of a specific functional area, or can be as small as a single sub-pixel.

[0169] In this specification, the meaning of specific substance A contained in layer B includes i) the case where one or more substances A are contained in one layer B, and ii) the case where layer B is composed of one or more layers and substance A is contained in one or more layers of the multiple layers B.

[0170] In this specification, the meaning of a specific substance A being contained in layer C or layer D refers to all of the following situations: i) being contained in one or more layers among one or more layers C, or ii) being contained in one or more layers among one or more layers D, or iii) being contained in one or more layers C and one or more layers D, respectively.

[0171] In this specification, the "evaporation temperature" of a substance is the temperature at which the substance evaporates at a given distance from the source of evaporation of the substance being evaporated. / sec evaporation speed, at 1×10 -6 Torr to 1×10 -9 The measurement is performed in a sublimation crucible of a vacuum evaporation tool such as a VTE chamber (vacuum thermal evaporation chamber) under a constant pressure of 100°C. As understood by those skilled in the art, various measurement values ​​(e.g., temperature, pressure, evaporation rate, etc.) described in this specification are expected to have nominal variations due to expected fair errors in the measurement of the calculated quantitative values.

[0172] One embodiment of the present specification provides an organic light-emitting device, which includes: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, and one or more of the organic layers contains the compound of the above chemical formula 1.

[0173] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, it 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, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0174] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

[0175] According to one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound as a host of the light-emitting layer.

[0176] According to one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes a fluorescent dopant.

[0177] According to one embodiment of the present specification, the fluorescent dopant is a pyrene-based compound or a non-pyrene-based compound.

[0178] According to one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

[0179] According to one embodiment of the present specification, the light-emitting layer further includes one or more hosts different from the compound of Chemical Formula 1.

[0180] The host different from the compound of the above Chemical Formula 1 may be used without limitation as long as it is different from the above Chemical Formula 1 and is an anthracene-based host used in the technical field, and is not limited thereto.

[0181] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant.

[0182] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the host includes the compound represented by Chemical Formula 1.

[0183] According to one embodiment of the present specification, the dopant is a blue dopant.

[0184] According to one embodiment of the present specification, the organic light-emitting device is a blue organic light-emitting device.

[0185] According to one embodiment of the present specification, the light-emitting layer includes two or more mixed hosts, and one or more of the two or more mixed hosts includes the compound represented by Chemical Formula 1.

[0186] According to one embodiment of the present specification, the light-emitting layer includes two or more mixed hosts, at least one of the two or more mixed hosts includes a compound represented by Chemical Formula 1, and the rest includes anthracene compounds different from Chemical Formula 1.

[0187] At least one of the above two or more mixed hosts contains the compound represented by the above Chemical Formula 1, and the others can be used without limitation as long as they are different from the above Chemical Formula 1 and are anthracene-based hosts used in the technical field, and are not limited thereto.

[0188] An organic light-emitting device using two or more mixed hosts according to one embodiment of the present specification mixes the advantages of each host to improve the performance of the device. For example, when mixing two hosts, one host with high efficiency and low voltage effects and one host with long life effects can be mixed to produce an organic light-emitting device with high efficiency, low voltage and long life effects.

[0189] According to one embodiment of the present specification, the light-emitting layer has two or more layers, and one or more layers of the two or more light-emitting layers include the compound of Chemical Formula 1.

[0190] According to one embodiment of the present specification, the light-emitting layer has two or more layers, one or more of the two or more light-emitting layers includes two or more mixed hosts, and one or more of the two or more mixed hosts includes the compound of Chemical Formula 1.

[0191] According to one embodiment of the present specification, the light-emitting layer includes two layers, and one of the two light-emitting layers includes the compound of Chemical Formula 1.

[0192] According to one embodiment of the present specification, the light-emitting layer comprises two layers, one of the two light-emitting layers comprises two or more mixed hosts, and one or more of the two or more mixed hosts comprises the compound of Chemical Formula 1.

[0193] The above two or more mixed entities are the same as described above.

[0194] According to one embodiment of the present specification, the maximum emission wavelength (λ max ) is 400nm to 470nm.

[0195] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant is a fluorescent dopant.

[0196] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the dopant includes one or more selected from pyrene-based compounds and non-pyrene-based compounds.

[0197] The above-mentioned pyrene-based compounds and non-pyrene-based compounds can be used without limitation as long as they are compounds used in the present technical field, and are not limited thereto.

[0198] According to one embodiment of the present specification, the non-pyrene-based compound includes a boron-based compound.

[0199] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, the host includes the compound represented by the above Chemical Formula 1, and the dopant includes at least one selected from pyrene compounds and non-pyrene compounds.

[0200] According to one embodiment of the present specification, the light-emitting layer includes a host and a dopant, and the light-emitting layer includes the host:dopant in a weight ratio of 0.1:99.9 to 20:80.

[0201] According to another embodiment of the present specification, a cover layer is provided on a surface opposite to a surface of at least one of the first electrode and the second electrode that faces the organic layer.

[0202] The above-mentioned covering layer is formed to prevent a large amount of light from being lost through total reflection in the organic light-emitting device. The covering layer has the ability to fully protect the lower cathode and light-emitting layer from external moisture penetration or contamination, and has a high refractive index to prevent light loss due to total reflection.

[0203] According to another embodiment of the present specification, the cover layer may be provided on a surface of the first electrode opposite to a surface facing the organic layer and a surface of the second electrode opposite to a surface facing the organic layer.

[0204] According to another embodiment of the present specification, the cover layer may be provided on a surface of the first electrode opposite to a surface thereof facing the organic layer.

[0205] According to another embodiment of the present specification, the cover layer may be provided on a surface of the second electrode opposite to a surface thereof facing the organic layer.

[0206] According to one embodiment of the present specification, the organic light-emitting device further includes one or more layers selected from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer and an electron blocking layer.

[0207] According to one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode arranged opposite to the first electrode; a light-emitting layer arranged between the first electrode and the second electrode; and two or more organic layers arranged between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0208] According to one embodiment of the present specification, the two or more organic layers between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, can be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole injection and transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer. Two or more.

[0209] According to one embodiment of the present specification, two or more hole transport layers are included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different substances.

[0210] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0211] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0212] According to one embodiment of the present specification, the organic light emitting device may be a (normal type) organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0213] According to one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0214] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is shown in Figure 1 and 2 . The above Figure 1 and Figure 2 An organic light emitting device is exemplified, and is not limited thereto.

[0215] Figure 1 exemplifies the structure of an organic light-emitting device in which a first electrode 2, a light-emitting layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The above-mentioned compound is contained in the light-emitting layer.

[0216] Figure 2 exemplifies the structure of an organic light-emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, a hole adjustment layer 7, a light-emitting layer 4, an electron adjustment layer 8, an electron transport layer 9, an electron injection layer 10, a second electrode 3 and a capping layer 11 are sequentially stacked on a substrate 1. The above compound is contained in the light-emitting layer.

[0217] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that the light-emitting layer includes the above compound, ie, the compound of the above Chemical Formula 1.

[0218] 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.

[0219] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, the device can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, 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 on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a second electrode substance, an organic layer, and a first electrode substance on a substrate.

[0220] In addition, the compound represented by the above chemical formula 1 can be used to form an organic layer by not only vacuum evaporation but also solution coating when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0221] In addition to these methods, the organic light-emitting device can also be manufactured by sequentially vapor-depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. However, the manufacturing method is not limited thereto.

[0222] As the first electrode material, in order to smoothly inject holes into the organic layer, a material with a large work function is preferred. For example, there are metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); 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, etc., but are not limited thereto.

[0223] As the second electrode material, in order to facilitate electron injection into the organic layer, a material with a small work function is preferably used, for example, 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 not limited thereto.

[0224] The light-emitting layer may include a host material and a dopant material. When another light-emitting layer is included in addition to the light-emitting layer including the compound of the above Chemical Formula 1 according to one embodiment of the present specification, the host material includes a condensed and / or non-condensed aromatic ring derivative or a heterocyclic compound. Specifically, as the condensed aromatic ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as the heterocyclic compound, there are dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0225] As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are fused aromatic ring derivatives having substituted or unsubstituted arylamine groups, and there are pyrene, anthracene, In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamine. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0226] According to one embodiment of the present specification, the dopant material includes a compound of the following chemical formula D-1 or D-2, but is not limited thereto.

[0227] [Chemical formula D-1]

[0228]

[0229] In the above chemical formula D-1,

[0230] L101 and L102 are the same or different from each other, and are each independently a directly bonded, or substituted or unsubstituted arylene group,

[0231] Ar101 to Ar104 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,

[0232] [Chemical formula D-2]

[0233]

[0234] In the above chemical formula D-2,

[0235] 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,

[0236] t3 and t4 are each an integer from 1 to 4,

[0237] t5 is an integer from 1 to 3,

[0238] When the above t3 is 2 or more, the above two or more T3 are the same or different from each other.

[0239] When the above t4 is 2 or more, the above two or more T4 are the same or different from each other.

[0240] When the above t5 is 2 or more, the above two or more T5s may be the same as or different from each other.

[0241] According to one embodiment of the present specification, L101 and L102 are directly bonded.

[0242] According to one embodiment of the present specification, Ar101 to Ar104 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 substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0243] According to one embodiment of the present specification, the above-mentioned Ar101 to Ar104 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted by a linear or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

[0244] According to one embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a phenyl group substituted with a methyl group, or a dibenzofuranyl group.

[0245] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0246]

[0247] 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.

[0248] 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.

[0249] According to one embodiment of the present specification, the above T1 to T5 are the same as or different from each other, and are each independently hydrogen, methyl, tert-butyl, diphenylamino, or phenyl which may be substituted or unsubstituted by methyl or tert-butyl.

[0250] According to one embodiment of the present specification, the chemical formula D-2 is represented by the following compound.

[0251]

[0252] The hole injection layer is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, has the effect of receiving holes from the anode, and has an excellent hole injection effect for the light-emitting layer or the light-emitting material. In addition, it is preferably a material that has an excellent ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. In addition, it is preferably a material with excellent thin film forming ability. In addition, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, and arylamine organics; hexanitrile hexaazatriphenylene organics; quinacridone organics; perylene organics; anthraquinone, polyaniline, and polythiophene conductive polymers, etc., but are not limited to these.

[0253] According to one embodiment of the present specification, the hole injection layer includes a compound of the following chemical formula HI-1, but is not limited thereto.

[0254] [Chemical formula HI-1]

[0255]

[0256] In the above chemical formula HI-1,

[0257] At least one of X'1 to X'6 is N, and the others are CH,

[0258] R309 to R314 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted amine, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0259] According to one embodiment of the present specification, X'1 to X'6 are N.

[0260] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0261] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0262]

[0263] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. 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, preferably a material with a large mobility for holes. As specific examples, there are arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0264] The hole regulating layer is a layer that can improve the life and efficiency of the device by regulating the holes transferred from the hole transport layer to be smoothly injected into the light-emitting layer, preventing the electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. Known materials can be used without limitation, and the layer can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[0265] According to one embodiment of the present specification, the hole transport layer or the hole regulation layer includes a compound of the following chemical formula HT-1, but is not limited thereto.

[0266] [Chemical formula HT-1]

[0267]

[0268] In the above chemical formula HT-1,

[0269] R315 to R317 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 heteroaryl, and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring,

[0270] r315 is an integer from 1 to 5. When the above r315 is 2 or more, the two or more R315 are the same or different from each other.

[0271] r316 is an integer of 1 to 5. When the number of r316 is 2 or more, two or more R316 are the same as or different from each other.

[0272] According to one embodiment of the present specification, the above R317 is any one selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a combination thereof.

[0273] According to one embodiment of the present specification, the R317 is any one selected from a carbazolyl group, a phenyl group, a biphenyl group, and a combination thereof.

[0274] According to one embodiment of the present specification, R315 and R316 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.

[0275] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and are independently phenyl or phenanthryl, or are combined with adjacent groups to form an indene substituted with a methyl group.

[0276] According to one embodiment of the present specification, the chemical formula HT-1 is represented by any one of the following compounds.

[0277]

[0278] The electron regulating layer is a layer for regulating smooth injection of electrons transferred from the electron transporting layer into the light emitting layer, and any known material can be used without limitation.

[0279] According to one embodiment of the present specification, the electron adjustment layer includes a compound of the following chemical formula EG-1, but is not limited thereto.

[0280] [Chemical formula EG-1]

[0281]

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

[0283] At least one of G'1 to G'18 is -L5-Ar5, and the others are hydrogen, or G'1 and G'18 are connected by -L51- to form a substituted or unsubstituted ring,

[0284] L5 is a direct bond, or a substituted or unsubstituted arylene group,

[0285] Ar5 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

[0286] L51 is O or S.

[0287] According to one embodiment of the present specification, the above-mentioned L51 is O.

[0288] According to one embodiment of the present specification, the above-mentioned L51 is S.

[0289] According to one embodiment of the present specification, the above G'1 and G'18 are linked by -L51- to form a substituted or unsubstituted heterocyclic ring.

[0290] According to one embodiment of the present specification, the above G'1 and G'18 are linked by -L51- to form a substituted or unsubstituted xanthene ring or a substituted or unsubstituted thioxanthene ring.

[0291] According to one embodiment of the present specification, the above G'1 and G'18 are linked by -O- to form a substituted or unsubstituted xanthene ring.

[0292] According to one embodiment of the present specification, the above G'1 and G'18 are linked by -S- to form a substituted or unsubstituted thioxanthene ring.

[0293] According to one embodiment of the present specification, G'1 and G'18 are linked by -O- to form a xanthene ring.

[0294] According to one embodiment of the present specification, the G'1 and G'18 are linked by -S- to form a thioxanthene ring.

[0295] According to one embodiment of the present specification, the above-mentioned L5 is a directly bonded or substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0296] According to one embodiment of the present specification, the above-mentioned L5 is a directly bonded or substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0297] According to one embodiment of the present specification, the above-mentioned L5 is a direct bond, or a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0298] According to one embodiment of the present specification, the above-mentioned L5 is a direct bond, or a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

[0299] According to one embodiment of the present specification, the above-mentioned L5 is a direct bond or a phenylene group.

[0300] According to one embodiment of the present specification, the Ar5 is a substituted or unsubstituted triazine group.

[0301] According to one embodiment of the present specification, Ar5 is a triazine group which is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0302] According to one embodiment of the present specification, Ar5 is a triazine group substituted with a phenyl group.

[0303] According to one embodiment of the present specification, the above EG-1 is represented by the following compound.

[0304]

[0305] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, preferably a material with a large mobility for electrons. 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 electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, a suitable cathode material is a common material having a low work function and accompanied by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, etc., in each case accompanied by an aluminum layer or a silver layer.

[0306] According to one embodiment of the present specification, the electron transport layer includes a compound of the following chemical formula ET-1, but is not limited thereto.

[0307] [Chemical formula ET-1]

[0308]

[0309] In the above chemical formula ET-1,

[0310] At least one of Z11 to Z13 is N, and the rest are CH,

[0311] L601 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0312] Ar601 and Ar602 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,

[0313] l601 is an integer from 1 to 5. When the above l601 is 2 or more, the above two or more L601 are the same as or different from each other.

[0314] 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.

[0315] According to one embodiment of the present specification, the L601 is a phenylene group, a biphenylene group, or a naphthylene group.

[0316] According to one embodiment of the present specification, Ar601 and Ar602 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms.

[0317] According to one embodiment of the present specification, Ar601 and Ar602 are phenyl groups.

[0318] According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0319]

[0320] The electron injection layer is a layer that receives electrons from the electrode. As the electron injection material, preferably, the following materials are used: materials that have excellent ability to transport electrons, have the effect of receiving electrons from the second electrode, and have excellent electron injection effect on the light-emitting layer or the light-emitting material. In addition, materials that prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer and have excellent thin film forming ability are preferred. 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.

[0321] 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.

[0322] The electron blocking layer is a layer that prevents the electrons injected from the electron injection layer from entering the hole injection layer through the light-emitting layer, thereby improving the life and efficiency of the device. Known materials can be used without restriction, and can be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and the layer that simultaneously performs hole injection and hole transport.

[0323] 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, and aluminum complexes.

[0324] The above-mentioned covering layer is formed to prevent a large amount of light from being lost through total reflection of light in the organic light-emitting device. The covering layer has the property of fully protecting the lower cathode and the light-emitting layer from external moisture penetration or contamination. It has a high refractive index and can prevent light loss due to total reflection, and existing materials can be used without restrictions.

[0325] According to one embodiment of the present specification, the cover layer includes a compound represented by the following chemical formula CP-1, but the present invention is not limited thereto.

[0326] [Chemical formula CP-1]

[0327]

[0328] In the above chemical formula CP-1,

[0329] L501 and L502 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,

[0330] R501 and Ar501 to Ar504 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, or adjacent groups are combined to form a substituted or unsubstituted ring.

[0331] According to one embodiment of the present specification, L501 and L502 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0332] According to one embodiment of the present specification, L501 and L502 are phenylene groups.

[0333] According to one embodiment of the present specification, the above R501 and Ar501 to Ar504 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, or are combined with adjacent groups to form a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0334] According to one embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups, or are combined with adjacent groups to form carbazole substituted or unsubstituted with a phenyl group.

[0335] According to one embodiment of the present specification, Ar501 and L501 are bonded to form a carbazole substituted with a phenyl group.

[0336] According to one embodiment of the present specification, Ar503 and L503 are bonded to form a carbazole substituted with a phenyl group.

[0337] According to one embodiment of the present specification, the chemical formula CP-1 is represented by the following compound.

[0338]

[0339] One embodiment of the present invention provides an organic light-emitting device, which includes: an anode; a cathode; a first light-emitting layer arranged between the anode and the cathode; and a second light-emitting layer arranged between the first light-emitting layer and the cathode and connected to the first light-emitting layer, the first light-emitting layer contains the compound of the above chemical formula 1, and the second light-emitting layer contains at least one compound of the compound of the following chemical formula 2 and the compound of chemical formula 3.

[0340] [Chemical formula 2]

[0341]

[0342] In the above chemical formula 2,

[0343] At least one of R11 to R20 is bonded to the * site of the following chemical formula 2-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group,

[0344] [Chemical formula 2-1]

[0345]

[0346] L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0347] Ar2 is a substituted or unsubstituted aryl group,

[0348] p is an integer from 1 to 3,

[0349] [Chemical formula 3]

[0350]

[0351] In the above chemical formula 3,

[0352] At least one of Y1 to Y10 is bonded to the * site of the following chemical formula 3-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group,

[0353] [Chemical formula 3-1]

[0354]

[0355] A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle,

[0356] L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0357] q is an integer from 1 to 3.

[0358] In one embodiment of the present specification, the first light-emitting layer and the second light-emitting layer may be provided in contact with each other.

[0359] Figure 3 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, a hole adjustment layer 7, a first light-emitting layer 4-1, a second light-emitting layer 4-2, an electron adjustment layer 8, an electron transport layer 9, an electron injection layer 10, a second electrode 3 and a covering layer 11 are sequentially stacked on a substrate 1.

[0360] In one embodiment of the present specification, the first light-emitting layer includes the compound as a main body of the first light-emitting layer, and the second light-emitting layer may include at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 as a main body of the second light-emitting layer. In this case, the first light-emitting layer and the second light-emitting layer each further include a dopant, and the dopant may include a fluorescent dopant. The dopant included in the first light-emitting layer and the second light-emitting layer may be similarly applicable to the description of the dopant.

[0361] In one embodiment of the present specification, the second light-emitting layer may include the compound of Chemical Formula 2 or the compound of Chemical Formula 3. The second light-emitting layer may include the compound of Chemical Formula 2 and the compound of Chemical Formula 3.

[0362] According to one embodiment of the present specification, the deuterium substitution rates of the above Chemical Formulas 2 and 3 are each 0.1% to 100%.

[0363] According to one embodiment of the present specification, the deuterium substitution rates of the above Chemical Formulas 2 and 3 are each 1% to 100%.

[0364] According to one embodiment of the present specification, the deuterium substitution rates of the above Chemical Formulas 2 and 3 are each 40% to 99%.

[0365] According to one embodiment of the present specification, when the above chemical formula 2 or 3 contains deuterium, the following effects are achieved. Specifically, the physical and chemical properties such as the bond length of the chemical bond related to deuterium are different from those of hydrogen. Compared with the CH bond, the stretching amplitude of the CD bond is smaller, so the van der Waals radius of deuterium is smaller than that of hydrogen. Generally, it can be shown that the CD bond is shorter and stronger than the CH bond. Therefore, when the hydrogen at the substitutable position of the above chemical formula 1 is replaced by deuterium, the energy of the ground state is reduced, the bond length of deuterium and carbon is shortened, and thus the molecular hardcore volume is reduced, so the electrical polarizability can be reduced, and the intermolecular interaction is weakened, thereby increasing the film volume. In addition, such characteristics can produce the effect of reducing the crystallinity of the film, that is, the amorphous state, which can generally effectively improve the life and driving characteristics of the organic light-emitting device, and the heat resistance can be further improved compared with the existing organic light-emitting device.

[0366] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0367] The present inventors have discovered suitable conditions applicable to benzo[ghi]fluoranthene-type hosts (hereinafter, compounds of Chemical Formula 1) and anthracene-type hosts (hereinafter, compounds of Chemical Formula 2 or 3) that are useful as blue fluorescent host materials and can provide stable co-evaporation mixtures after premixing.

[0368] The light-emitting layer of an organic light-emitting device that shows excellent life and efficiency requires more than 2 components (for example, 3 or 4 components). For this purpose, it is required to manufacture such a light-emitting layer with 3 or 4 raw materials, which is very complicated and costly compared to a standard two-component light-emitting layer with a single host and a dopant that only requires 2 raw materials. Premixing more than 2 substances and evaporating them from one raw material can reduce the complexity of the manufacturing process. The selected hole transport host and other types of hosts, such as electron transport hosts, can be mixed and co-evaporated in one crucible, so that stable evaporation can be achieved.

[0369] However, the co-evaporation must be stable, i.e. the composition of the evaporated film must remain constant during the manufacturing process. Any compositional changes may have an adverse effect on the device performance. In order to obtain a stable co-evaporation based on a mixture of compounds under vacuum, it can be assumed that the substances should have the same evaporation temperature under the same conditions. However, this should not be the only parameter to be considered. When two compounds are mixed together, they can interact with each other and their evaporation characteristics can differ from their individual characteristics. On the other hand, substances with slightly different evaporation temperatures can generate stable co-evaporated mixtures. Therefore, it is extremely difficult to achieve stable co-evaporated mixtures. To date, although there are tens of thousands of usable host substances in the literature, there are very few examples of stable co-evaporated mixtures. The "evaporation temperature" of a substance is the temperature at which the evaporated substance evaporates on a surface at a set distance from the evaporation source of the evaporated substance. / sec evaporation speed, at 1×10 -6 Torr to 1×10 -9 The various measured values ​​described in this specification, such as temperature, pressure, evaporation rate, etc., are expected to have nominal variations due to expected fair errors in the determination of the calculated quantitative values, as understood by those skilled in the art.

[0370] In the disclosure of this specification, a new type of two different types of anthracene hosts (chemical formulas 2 and 3) that are premixed and useful as blue fluorescent host materials and can provide a stable co-evaporation mixture is described. Multiple factors other than temperature can contribute to evaporation, for example, the miscibility of different substances, different phase changes. The inventors have found that when two substances have similar evaporation temperatures, similar mass reduction rates or similar vapor pressures, the two substances can be continuously co-evaporated. The mass reduction rate is defined as the percentage of mass reduction change according to time (minutes), as measured by thermogravimetric analysis (TGA) under the same experimental conditions at the same given constant temperature for each compound after the composition reaches a normal evaporation state, and is determined by measuring the time required for the initial 10% mass reduction. The given constant temperature is a temperature point selected in such a way that the mass reduction rate value becomes about 0.05% / minute to 0.50% / minute. Those skilled in the art will understand that in order to compare two parameters, the experimental conditions must be constant. The method of measuring the mass reduction rate and the vapor pressure is known in the art, and can be found in, for example, the document “Bull. et al. Mater. Sci. 2011, 34, 7”.

[0371] In the prior art, two components of the blue fluorescent host are mixed. The prior art document of the present invention is disclosed in the suggested JP 6328890 B2. In order to produce a blue fluorescent light-emitting layer with such a mixed host material, three evaporation sources are required: two hosts and a blue fluorescent dopant. The concentration of the co-host and the dopant is important for the device performance. Usually, the evaporation rate of each component is measured separately during the evaporation process. This makes the manufacturing process complicated and costly. Therefore, it is preferred to mix more than two components to reduce the amount of raw materials.

[0372] When two blue fluorescent hosts are premixed and the mixture is made by thermal sublimation, if the difference in composition is below a certain range, it means that they can be co-deposited from one raw material. Uniform co-deposition of the two hosts is important for the performance sustainability of the device made from the mixture.

[0373] Next, the compound represented by Chemical Formula 2 is described in detail.

[0374] According to one embodiment of the present specification, 1 to 3 of the above R11 to R20 are bonded to the * portion of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0375] According to another embodiment, 1 to 3 of the above R11 to R20 are bonded to the * portion of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0376] In another embodiment, the above R19 and R20 are bound to the * portion of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0377] According to another embodiment, the above R19, R20 and R18 are bound to the * portion of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0378] In another embodiment, the above R19, R20 and R17 are bound to the * portion of the above Chemical Formula 2-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0379] According to one embodiment of the present specification, the substituents in R11 to R20 that are not bonded to the chemical formula 2-1 are the same as or different from each other, and are each independently hydrogen, deuterium or dibenzofuranyl.

[0380] According to one embodiment of the present specification, the above p is an integer of 3, and the three L2s are the same as or different from each other.

[0381] In another embodiment, the above p is an integer of 2, and the two L2 are the same as or different from each other.

[0382] According to one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

[0383] In another embodiment, L2 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.

[0384] According to another embodiment, L2 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0385] In another embodiment, L2 is a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, a naphthylene group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or a triphenylene group substituted or unsubstituted by deuterium.

[0386] According to one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Ar2 may be substituted with deuterium.

[0387] In another embodiment, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0388] According to another embodiment, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0389] In another embodiment, Ar2 is phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, terphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthryl substituted or unsubstituted by deuterium, or triphenylene substituted or unsubstituted by deuterium.

[0390] The compound of the above Chemical Formula 2 may be compounds described in JP 4070676 B2, KR 1477844 B1, US 6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082 B2, JP 5015459 B2, KR 1979037 B1, KR1550351 B1, KR 1503766 B1, KR 0826364 B1, KR 0749631 B1, KR 1115255 B1, KR 1538534 B1, etc.

[0391] Next, the compound represented by Chemical Formula 3 is described in detail.

[0392] According to one embodiment of the present specification, at least one of the above Y1 to Y10 is bonded to the * site of the above Chemical Formula 3-1, and the rest are hydrogen, deuterium, or a substituted or unsubstituted aromatic group having 6 to 60 carbon atoms.

[0393] According to one embodiment of the present specification, one to three of the above Y1 to Y10 are bound to the * portion of the above Chemical Formula 3-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0394] In one embodiment of the present specification, one to three of the above Y1 to Y10 are bonded to the * portion of the above chemical formula 3-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or a substituted or unsubstituted silyl group.

[0395] In another embodiment, the above Y7, Y8 or Y9 is bound to the * portion of the above Chemical Formula 3-1, and the rest is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0396] According to another embodiment, the above Y7 and Y9 are bound to the * portion of the above Chemical Formula 3-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0397] According to another embodiment, the above Y9 and Y10 are bound to the * portion of the above Chemical Formula 3-1, and the rest are hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group.

[0398] According to one embodiment of the present specification, the substituents not bound to the above Chemical Formula 3-1 among Y1 to Y10 are the same as or different from each other, and are independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. The substituents not bound to the above Chemical Formula 2-1 among Y1 to Y10 may be substituted with deuterium.

[0399] According to another embodiment, the substituents in the above Y1 to Y10 that are not combined with the above Chemical Formula 3-1 are the same as or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, or substituted or unsubstituted triphenylene, and the above substituents may be further substituted by deuterium, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, terphenyl substituted or unsubstituted by deuterium, naphthyl substituted or unsubstituted by deuterium, phenanthryl substituted or unsubstituted by deuterium, or triphenylene substituted or unsubstituted by deuterium.

[0400] In one embodiment of the present specification, the above q is an integer of 1 to 3, and when the above q is 2 or more, two or more L3 are the same as or different from each other.

[0401] According to one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms. L2 may be substituted with deuterium.

[0402] In another embodiment, L3 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.

[0403] According to another embodiment, L3 is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0404] In another embodiment, L3 is a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, a naphthylene group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or a triphenylene group substituted or unsubstituted by deuterium.

[0405] According to one embodiment of the present specification, A and B are the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 2 to 60 carbon atoms.

[0406] In one embodiment of the present specification, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups substituted or unsubstituted with deuterium, or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups substituted or unsubstituted with deuterium.

[0407] According to another embodiment, A and B are the same as or different from each other, and are each independently an aromatic hydrocarbon ring having 6 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted with deuterium, or an aromatic heterocyclic ring having 2 to 60 carbon atoms, which is substituted or unsubstituted with one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted with deuterium.

[0408] In another embodiment, A and B are the same as or different from each other, and are each independently substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, or substituted or unsubstituted dibenzofuran.

[0409] According to another embodiment, A and B are the same as or different from each other, and are each independently benzene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, naphthalene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, phenanthrene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, triphenylene substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium, or dibenzofuran substituted or unsubstituted by one or more substituents selected from deuterium and aryl groups having 6 to 30 carbon atoms which are substituted or unsubstituted by deuterium.

[0410] The compound of the above Chemical Formula 3 may be a compound described in KR 1964435 B1, KR 1899728 B1, KR 1975945 B1, KR 2018-0098122 A, KR 2018-0102937 A, KR 2018-0103352 A, KR 1538534 B1, etc.

[0411] The organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0412] Modes for Carrying Out the Invention

[0413] Below, in order to specifically describe the application, embodiments will be cited to describe in detail. However, various forms can be deformed according to the embodiments of the application, and it is not interpreted that the scope of the application is limited to the embodiments described in detail below. The embodiments of the application are provided to more completely describe the application to those skilled in the art.

[0414] <Production Example 1> Synthesis of Chemical Formula 1

[0415] Synthesis of Chemical Formula A1 and B1

[0416]

[0417] After SM1 (1 equivalent) and SM2 (1.1 equivalent) were added to tetrahydrofuran (excess), a 2M potassium carbonate aqueous solution (30 volume ratio relative to THF) was added, and tetrakis(triphenylphosphine)palladium (2 mol%) was added, followed by heating and stirring at 85°C for 10 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate aqueous solution was removed, the layers were separated, and column chromatography was performed using hexane and ethyl acetate to produce the above-mentioned chemical formulas A1 and B1.

[0418] In the synthesis method of the above chemical formulas A1 and B1, except that SM1 and SM2 were changed as shown in Table 1 below, A1-1 to A1-3 and B1-1 to B1-3 in Table 1 below were synthesized by the same method.

[0419] [Table 1]

[0420]

[0421] Synthesis of chemical formula A2 and B2

[0422]

[0423]

[0424] After SM1 (one of A1 or B1, 1 equivalent) was dissolved in dichloromethane (DCM), triethylamine (1.2 equivalent) was added dropwise, and after stirring for 1 hour, trifluoroacetic acid (1.1 equivalent) was slowly added and stirred for 3 hours. After confirming the completion of the reaction, the reaction was terminated with water, and after extraction, column chromatography was performed with hexane and ethyl acetate to produce the above-mentioned chemical formulas A2 and B2.

[0425] In the synthesis method of the above chemical formulas A2 and B2, except that SM1 and SM2 were changed as shown in Table 2 below, A2-1 to A2-3 and B2-1 to B2-3 in Table 2 below were synthesized by the same method.

[0426] [Table 2]

[0427]

[0428] Synthesis of chemical formula A3 and B3

[0429]

[0430]

[0431] SM1 (one of A2 and B2, 1 equivalent), trimethylsilyl acetylene (5 equivalents), tetrakis(triphenylphosphine)palladium (0.1 equivalent), copper iodide (CuI, 1 equivalent) and triethylamine (excess) were added, and heated and stirred at 95°C for 5 hours. After the reaction was completed, it was cooled to room temperature, passed through a filter filled with diatomaceous earth / silica gel, washed with chloroform, and the solvent was removed, and column chromatography was performed with hexane and ethyl acetate to produce the above chemical formulas A3 and B3.

[0432] In the synthesis method of the above chemical formulas A3 and B3, except that SM1 and SM2 were changed as shown in Table 3 below, A3-1 to A3-3 and B3-1 to B3-3 in Table 3 below were synthesized by the same method.

[0433] [Table 3]

[0434]

[0435] Synthesis of chemical formula A4 and B4

[0436]

[0437] SM1 (one of A3 and B3, 1 equivalent), platinum chloride (0.05 equivalent) and toluene (excess) were added, stirred at 95°C for 3 hours, and after confirming the completion of the reaction, cooled to room temperature. After filtering through a diatomaceous earth / silica gel pad and removing the solvent by reduced pressure distillation, column chromatography was performed with hexane and ethyl acetate to produce the above chemical formulas A4 and B4.

[0438] In the synthesis method of the above chemical formulas A4 and B4, except that SM1 and SM2 were changed as shown in Table 4 below, A4-1 to A4-3 and B4-1 to B4-3 in Table 4 below were synthesized by the same method.

[0439] [Table 4]

[0440]

[0441] Synthesis of Chemical Formula A5

[0442]

[0443]

[0444] SM1 (one of A4 and B4, 1 equivalent) was dissolved in dichloromethane (DCM, excess), and then boron tribromide (3 equivalents) was slowly added and stirred for 5 hours. After confirming the completion of the reaction, it was neutralized with sodium bicarbonate saturated water and then extracted. After the solvent was removed by vacuum distillation, column chromatography was performed with hexane and ethyl acetate to produce the above-mentioned chemical formula A5.

[0445] In the synthesis method of the above chemical formula A5, except that SM1 and SM2 were changed as shown in the following Table 5, A5-1 to A5-6 in the following Table 5 were synthesized by the same method.

[0446] [Table 5]

[0447]

[0448] Synthesis of Chemical Formula A6

[0449] Compound A5 (1 equivalent) was dissolved in chloroform (excess), and perfluorobutylsulfonyl fluoride (1.5 equivalents) and potassium carbonate (3 equivalents) were added, followed by stirring at room temperature for 6 hours. After confirming the completion of the reaction, the mixture was extracted three times with water, and then column chromatography was performed with hexane and ethyl acetate to produce the above-mentioned chemical formula A6.

[0450] In the synthesis method of the above chemical formula A6, except that SM1 and SM2 were changed as shown in the following Table 6, A6-1 to A6-6 in the following Table 6 were synthesized by the same method.

[0451] [Table 6]

[0452]

[0453] Synthesis of Chemical Formula A7

[0454]

[0455] Compound A6 (1 equivalent), 1,8-diazabicyclo[5,4,0]undec-7-ene (1.5 equivalents), and lithium chloride (1 equivalent) were added to DMF (excess), stirred and heated, and bis(triphenylphosphine)palladium dichloride (0.1 equivalent) was added dropwise at 120°C, stirred and refluxed for 12 hours. After confirming the completion of the reaction, the mixture was cooled to room temperature, ethanol and water were added, filtered, and purified by ethyl acetate and hexane column chromatography to produce the above-mentioned chemical formula A7.

[0456] In the synthesis method of the above chemical formula A7, except that SM1 and SM2 were changed as shown in the following Table 7, A7-1 to A7-6 in the following Table 7 were synthesized by the same method.

[0457] [Table 7]

[0458]

[0459] Synthesis of Chemical Formula A8

[0460]

[0461] Compound A7 (1 equivalent) and SM2 (1.3 equivalents) were added to 1,4-dihydro- Potassium acetate (3 equivalents) was added to 1,4-dioxane (12 times the mass ratio of SM1), stirred and refluxed. Bis(diphenylphosphino)ferrocenepalladium dichloride (0.05 equivalents) was added to 1,4-dioxane. After stirring in oxane for 5 minutes, the mixture was added. After 2 hours, the reaction was confirmed to be complete and the mixture was cooled to room temperature. After adding ethanol and water, the mixture was filtered and purified by recrystallization with ethyl acetate and ethanol to produce the above-mentioned chemical formula A8.

[0462] In the synthesis method of the above chemical formula A8, except that SM1 and SM2 were changed as shown in the following Table 8, A8-1 to A8-6 in the following Table 8 were synthesized by the same method.

[0463] [Table 8]

[0464]

[0465] Synthesis of Int

[0466]

[0467] After SM1 (1 equivalent) and SM2 (1.1 equivalent or 2.1 equivalent) were added to tetrahydrofuran (excess), a 2M potassium carbonate aqueous solution (30 volume ratio relative to THF) was added, and tetrakis(triphenylphosphine)palladium (2 mol%) was added, followed by heating and stirring at 85°C for 10 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate aqueous solution was removed, the layers were separated, and column chromatography was performed using hexane and ethyl acetate to produce the above chemical formula int.

[0468] In the synthesis method of the above chemical formula int., int 1. to int 12. in the following Table 9 were synthesized by the same method except that SM1 and SM2 were changed as shown in the following Table 9.

[0469] [Table 9]

[0470]

[0471]

[0472] Synthesis of Chemical Formula 1

[0473]

[0474] After SM1 (1 equivalent) and SM2 (1.1 equivalent or 1.1 equivalent per halogen number) were added to tetrahydrofuran (excess), a 2M potassium carbonate aqueous solution (30 volume ratio relative to THF) was added, and tetrakis(triphenylphosphine)palladium (2 mol%) was added, followed by heating and stirring at 85° C. for 10 hours. The temperature was lowered to room temperature, and after the reaction was terminated, the potassium carbonate aqueous solution was removed, the layers were separated, and column chromatography was performed with hexane and ethyl acetate to produce the above-mentioned chemical formula 1.

[0475] In the synthesis method of the above Chemical Formula 1, except that SM1 and SM2 were changed as shown in Table 10 below, Compounds 1 to 13 in Table 10 below were synthesized by the same method.

[0476] [Table 10]

[0477]

[0478]

[0479] Synthesis of Chemical Formula 1D

[0480] The reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst (cat.)) are added to C6D6 (10 to 50 times the mass ratio relative to the reactant), and stirred at 70°C for 10 to 100 minutes. After the reaction is completed, D2O (excess) is added, and after stirring for 30 minutes, trimethylamine (excess) is added dropwise. The reaction solution is transferred to a separatory funnel and extracted with water and chloroform. After the extract is dried with MgSO4, it is heated with toluene and recrystallized to obtain compounds 1-14 to 1-17 in Table 11 below.

[0481] [Table 11]

[0482]

[0483] The degree of deuterium substitution of each product varies depending on the reaction time and can be determined by the maximum m / z (M + ) value determines the substitution rate.

[0484] <Production Example 2-1> Synthesis of Chemical Formula 2

[0485]

[0486] The reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst) were added to C6D6 (10 to 50 times the mass ratio relative to the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction was completed, D2O (excessive) was added, and after stirring for 30 minutes, trimethylamine (excessive) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried with MgSO4 and recrystallized by heating with toluene to obtain the product shown in Table 12 below.

[0487] [Table 12]

[0488]

[0489]

[0490]

[0491]

[0492] The degree of deuterium substitution of each product varies depending on the reaction time and can be determined by the maximum m / z (M + ) value determines the substitution rate.

[0493] Compounds A to W as the above-mentioned reactants were synthesized with reference to existing documents such as JP 4070676 B2, KR 1477844B1, US6465115 B2, JP 3148176 B2, JP 4025136 B2, JP 4188082B2, JP 5015459 B2, KR 1979037B1, KR 1550351 B1, KR 1503766 B1, KR 0826364B1, KR 0749631B1, and KR 1115255B1. In addition, compounds 1-A to 1-W as deuterium-substituted products were synthesized with reference to the existing document KR 1538534 B1.

[0494] <Production Example 2-2> Synthesis of Chemical Formula 3

[0495]

[0496] The reactant (1 equivalent) and trifluoromethanesulfonic acid (catalyst) were added to C6D6 (10 to 50 times the mass ratio of the reactant) and stirred at 70°C for 10 to 100 minutes. After the reaction was completed, D2O (excessive) was added, and after stirring for 30 minutes, trimethylamine (excessive) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. After the extract was dried with MgSO4, it was heated with toluene and recrystallized to obtain the products shown in Tables 13 and 14 below.

[0497] [Table 13]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503] The degree of deuterium substitution of each product varies depending on the reaction time and can be determined by the maximum m / z (M + ) value determines the substitution rate.

[0504] Compounds 1# to 27# as the above-mentioned reactants were synthesized with reference to existing documents of our company such as KR 1964435B1, KR 1899728 B1, KR1975945B1, KR 2018-0098122 A, KR 2018-0102937A, and KR 2018-0103352 A. In addition, compounds 2-1 to 2-27 as deuterium-substituted products were synthesized with reference to the existing document KR 1538534 B1.

[0505] [Table 14]

[0506]

[0507]

[0508]

[0509]

[0510] The degree of deuterium substitution of each product varies depending on the reaction time and can be determined by the maximum m / z (M + ) value determines the substitution rate.

[0511] Compounds 28# to 47# as the above-mentioned reactants were synthesized with reference to our company's existing documents such as KR 1994238 B1, KR 1670193 B1, KR 1754445 B1, and KR 1368164 B1. In addition, compounds 2-28 to 2-47 as deuterium-substituted products were synthesized with reference to the existing document KR 1538534 B1.

[0512] Dipole moment (DM) and sublimation temperature of manufacturing example 2

[0513] [Table 15]

[0514]

[0515]

[0516] The physical properties of the compounds synthesized in the above-mentioned preparation examples are shown in the above-mentioned Table 15. Although compounds A to W have chemical structural differences in carbon-hydrogen skeletons and carbon-deuterium skeletons from compounds 1-A to 1-W, the basic chemical skeletons are the same, and the differences in dipole moments are almost the same, so the relevant numerical values ​​are collectively referred to as compounds A to W. In addition, compounds 1# to 47# are also the same as compounds 2-1 to compound 2-47, and the relevant numerical values ​​are collectively referred to as compounds 2-1 to compound 2-47.

[0517] In the compound synthesized in the above-mentioned manufacturing example, the compound equivalent to Chemical Formula 1 and the compound equivalent to Chemical Formula 2 have a difference in dipole moment in the chemical structure. Compounds A to W have a skeleton based only on carbon and hydrogen by having an aryl-based substituent, and form a limited number of electrons in the chemical structure. The more and less partitions, the more the dipole moment (DM) is not more than 0.3 Debye. On the contrary, it can be confirmed that compounds 1# to 47# have a potential that can deepen the electronic partition in the chemical structure with a carbon-hydrogen skeleton by replacing relatively electron-rich furans containing aryl or heteroaryl groups on the anthracene skeleton, and have a relatively high dipole moment (DM) compared to compounds A to W. Therefore, the combination of the two structures suggested in the present application has a range in which the difference in DM of the two main bodies is at least greater than 0.2.

[0518] l DM host1 –DM host2 l>0.2

[0519] Furthermore, it was confirmed that the sublimation temperature of the compound synthesized in the above production example was lower than 400° C. If the sublimation temperature was higher than 400° C., there would be many limitations in using the compound as a material for an organic electroluminescent device.

[0520] Furthermore, in order to pre-sublimate a mixture of one of the compounds corresponding to Chemical Formula 2 and one of the hosts corresponding to Chemical Formula 3, it is preferable that the following formula is satisfied.

[0521] [Formula 1]

[0522] |T sub1 -T sub2 |≤20℃

[0523] In the above formula 1, T sub1 is the sublimation temperature of the compound represented by the above chemical formula 2, T sub2 is the sublimation temperature of the compound represented by the above Chemical Formula 3.

[0524] When the above-mentioned constitution is satisfied, the low voltage and high efficiency provided by the compound represented by the above-mentioned chemical formula 2 are reproduced, and at the same time, the electron injection into the triplet energy level of the dopant provided by the compound represented by the above-mentioned chemical formula 3 becomes easy, thereby increasing the formation ratio of excitons, and thus having the advantage of improved luminous efficiency.

[0525] <Production Example 3> Production Example of Mixture

[0526] The premixability of two compounds (one compound each of Chemical Formula 2 and 3) corresponding to the two main bodies to be mixed was tested by high pressure liquid chromatography (HPLC) analysis of the evaporated film. In the preparation example of this mixture, Compound J (Chemical Formula 2) and Compound 6# (Chemical Formula 3) were used.

[0527] For this purpose, 0.15 g of Compound J (or Compound 1-J) and 0.15 g of Compound 6# (or Compound 2-6) were mixed in a ratio of 1:1 and crushed. 0.3 g of the mixture was placed in the evaporation source of a VTE vacuum chamber. The chamber was evacuated to reduce the pressure to 10 -7 torr. / second to evaporate on the glass substrate. In order to avoid cooling of the raw materials and keep them at an appropriate temperature, the evaporation process is not interrupted. After the film was formed, the substrate was replaced twice in succession. The evaporated film was analyzed by HPLC, and the results are shown below Figure 5 . Take 3 such substrate samples, represented by Film 1 to Film 3. The composition of Compound J (Chemical Formula 2) and Compound 6# (Chemical Formula 3) does not change significantly from Film 1 to Film 3. Through the entire process, the change in concentration before and after evaporation within 10%, preferably within 5%, is considered to be excellent and useful for commercial OLED applications, showing that the difference in sublimation temperature of the two mixed compounds can maintain the above-mentioned concentration change at a temperature difference of less than 20°C. The difference in sublimation temperature between the above-mentioned Compound J and Compound 6# is 10°C.

[0528] The slight variation in concentration shown below does not show any trend on the device, and the sample collection and HPLC analysis can be explained by the following formula 2. More specifically, the first compound (Compound J) or the second compound (Compound 6#) has a concentration C1 in the above mixture, and by mixing the above mixture with 1×10 -4 Torr to 1×10 -9 In high vacuum evaporation equipment with a chamber base pressure of to The film formed by evaporating the mixture at a predetermined distance from the place where the mixture is evaporated has a concentration C2 and satisfies the following formula 2.

[0529] [Formula 2]

[0530] l(C1-C2) / C1 l<10%

[0531] When the concentration C1 of the compound represented by compound 6# in the above composition is 48.85%, the concentration of membrane 1 is 47.69%, so the concentration change is 2.3%, the concentration of membrane 2 is 47.69%, so the concentration change is 3.9%, and the concentration of membrane 3 is 47.69%, so the concentration change is 2.3%.

[0532] The concentration change did not vary significantly in the prepared films 1 to 3, and it was observed that the variation between the films was small. Therefore, the above conditions are preferred.

[0533] <Production Example 4> Comparative Production Example of Mixture

[0534] The following are examples of mixtures that are not in the conditions described in this specification. In the following comparative preparation examples of mixtures, Compound B (Chemical Formula 2) and Compound 24# (Chemical Formula 3) were used.

[0535] For mixing, 0.21 g of compound B (or compound 1-B) and 0.09 g of compound 24# (or compound 2-24) were mixed in a ratio of 7:3 and crushed. The preparation conditions were the same as those of the mixture of the above-mentioned Preparation Example 3, and the results are shown below. Figure 6 .

[0536] According to the above formula 2, when the concentration C1 of the compound represented by compound B in the above composition is 69.30%, the concentration of membrane 1 is 65.42%, so the concentration change is 5.5%, the concentration of membrane 2 is 61.22%, so the concentration change is 11.6%, and the concentration of membrane 3 is 62.82%, so the concentration change is 9.3%.

[0537] In the films 1 to 3 produced, the concentration changes significantly varied, and in particular, a change of 10% or more was observed, and it was observed that there was a large variation between the films. Therefore, the above conditions are not preferred.

[0538] <Example 1> Fabrication of OLED

[0539] The ITO / Ag / ITO as anode is The substrate to be deposited was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water dissolved with a dispersant, and washed with ultrasound. The detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice by a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed in sequence with solvents of isopropanol, acetone, and methanol, and then dried.

[0540] On the anode prepared in this way, HI-1 was placed A hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 mm / s. On the hole injection layer, HT1 as a hole transporting material is deposited with a thickness of 1000 mm / s. Vacuum evaporation was performed to form a hole transport layer. Then, EB1 Then, as the first light-emitting layer, the host compound 1-11 synthesized in Preparation Example 1 and the dopant BD1 (2 wt %) were mixed in an amount of 1:1 to 2:1. Then, as the second light-emitting layer, the host compound A synthesized in Preparation Example 2 and the dopant BD1 (2 wt %) were mixed with Then, HB1 was evaporated to form a light-emitting layer. To form an electron regulating layer, the compound ET1 and Liq were mixed at a mass ratio of 5:5 to form a layer having a thickness of The electron transport layer of After forming a 1000-mm thick magnesium and lithium fluoride (LiF) film as an electron injection layer, a cathode is formed using magnesium and silver (1:4). After that, CP1 During the above process, the evaporation rate of the organic matter is maintained at

[0541]

[0542] <Comparative Examples 1 to 8 and Examples 1 to 86>

[0543] In the above Comparative Examples 1 to 8 and Examples 1 to 86, devices were manufactured by the same method as in Example 1, except that the substances described in Table 16 below were used as materials for the light-emitting layer.

[0544] For the devices manufactured in the above Comparative Examples 1 to 8 and Examples 1 to 86, the 2 The driving voltage, luminous efficiency, and time to 95% of the initial luminance (LT95) were measured at a current density of . The results are shown in Table 16 below.

[0545] [Table 16]

[0546]

[0547]

[0548]

[0549]

[0550]

[0551] The results in Table 16 above are for a device structure having two light-emitting layers, wherein the host of the first light-emitting layer and the host of the second light-emitting layer are a single host, and the host of the first light-emitting layer is constituted by the compound according to one embodiment of the present application.

[0552] The above-mentioned Comparative Examples 1 to 4 do not apply the compound according to one embodiment of the present application, and use the conventional aryl anthracene main body as the main body of the second light-emitting layer, and show lower efficiency and life compared with Examples 1 to 86, especially showing a significantly higher voltage. Among them, it can be seen that Comparative Examples 2 and 3 are structures in which the main body of the second light-emitting layer contains deuterium. Even if there is a certain degree of life improvement effect, it is significantly lower than that of the examples, and the overall device performance effect is not great. In addition, in Comparative Example 4 where BD2 as a boron-based blue dopant is applied, the trend of Comparative Example 2 is also maintained.

[0553] Comparative Examples 5 to 8 above do not use the compound according to one embodiment of the present application, and use the conventional heteroaryl anthracene main body as the main body of the second light-emitting layer. They also show low voltage compared with Comparative Examples 1 to 4, but also show low efficiency and life, and high voltage compared with Examples 1 to 86. Among them, it can be seen that Comparative Example 7 is the same as Comparative Examples 2 and 3 above, and the main body of the second light-emitting layer contains deuterium. Even if there is a certain degree of life improvement effect, it is significantly lower than the examples, and the overall device performance effect is not great. In addition, in Comparative Example 8 where BD2 as a boron-based blue dopant is used, the trend compared with Comparative Example 7 is also maintained.

[0554] In Examples 1 to 86 of the present application, it can be seen that the compound equivalent to Chemical Formula 1 is used as the main body of the first light-emitting layer, which plays a role in increasing the injection of holes and the potential barrier of electrons, and changes the light-emitting area within the light-emitting layer. As the main body of the second light-emitting layer, anthracene main bodies substituted with existing aromatic and heteroaromatic systems are used to maintain the low voltage characteristics and efficiency currently considered important in blue light-emitting devices, while ensuring the performance of the device.

[0555] In Examples 1 to 23, the compound according to one embodiment of the present application is used as the main body of the first light-emitting layer, and the aryl anthracene main body is used as the main body of the second light-emitting layer. The case where the H compound not suitable for deuterium is introduced as the main body of the second light-emitting layer (Examples 1, 5, 8, 12, 16, 19, 21) and the case where the D compound suitable for deuterium is introduced (the rest other than the above) are evaluated, and the effect of the two light-emitting layers is confirmed in each case. Data that can further improve the lifespan is seen by deuterium substitution of the main body of the second light-emitting layer. In addition, it can be confirmed that the device performance when the compound according to one embodiment of the present application is used as the main body of the first light-emitting layer is indeed improved.

[0556] In this regard, in Examples 24 to 27, the compounds of the claims were deuterated and used as the host of the first light-emitting layer, and the device results were compared as compared with Examples 5, 18, 17, and 21. It was observed that the lifetime of the first light-emitting layer formed adjacent to the hole regulating layer was further improved by deuterium substitution.

[0557] In Examples 28 to 31, only the blue dopant in the devices of Examples 24 to 27 above was changed from BD1 to BD2 and applied to each light-emitting layer, and the trend and performance of the device were confirmed. When BD2 was used as a boron-based dopant, it was confirmed that the efficiency was further improved while also maintaining the trend of improving the lifespan.

[0558] Examples 32 to 58 are different from Examples 1 to 23 in that anthracene derivatives combined with various heteroaryl groups such as dibenzofuran, naphthiobenzofuran, and triphenyldifuran are introduced as the main body of the second light-emitting layer. Although they show characteristics of relatively lower voltage and lower lifetime compared to Examples 1 to 23, in a device structure prepared by using a compound according to one embodiment of the present application as the main body of the first light-emitting layer, it can be confirmed that the device is improved while maintaining the characteristics as in the above-mentioned Examples 1 to 23.

[0559] In Examples 79 to 86, changes were introduced as in the results of Examples 24 to 31, and the results also showed excellent device performance.

[0560] <Example 87> Production of OLED

[0561] The ITO / Ag / ITO as anode is The deposited substrate was cut into a size of 50 mm × 50 mm × 0.5 mm, placed in distilled water dissolved with a dispersant, and washed with ultrasound. The detergent used was a product of Fischer Co., and the distilled water used was distilled water filtered twice by a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was performed in sequence with solvents of isopropanol, acetone, and methanol, and then dried.

[0562] On the anode prepared in this way, HI-1 was placed A hole injection layer is formed by thermal vacuum deposition with a thickness of 1000 mm / s. On the hole injection layer, HT1 as a hole transporting material is deposited with a thickness of 1000 mm / s. Vacuum evaporation was performed to form a hole transport layer. Then, EB1 Then, as the first light-emitting layer, the host compound 1-2 synthesized in Preparation Example 1 and the dopant BD1 (2 wt %) were mixed in an amount of 1:1. Then, as the second light-emitting layer, the host compound B synthesized in Preparation Example 2, the compound 2-3 synthesized in Preparation Example 2, and the dopant BD1 (2 wt %) were used. Then, HB1 was evaporated to form a light-emitting layer. To form an electron regulating layer, the compound ET1 and Liq were mixed at a mass ratio of 5:5 to form a layer having a thickness of The electron transport layer of After forming a 1000-mm thick magnesium and lithium fluoride (LiF) film as an electron injection layer, a cathode is formed using magnesium and silver (1:4). After that, CP1 was evaporated Thus, the device is completed. In the above process, the evaporation rate of the organic matter is maintained at

[0563]

[0564] <Comparative Examples 9 to 18 and Examples 87 to 122>

[0565] In the above Comparative Examples 9 to 18 and Examples 87 to 122, devices were manufactured by the same method as in Example 87, except that the substances described in Table 17 below were used as materials for the light-emitting layer.

[0566] However, regarding the host of the second light-emitting layer, as shown in the following Table 17, both of the following two cases are shown: an embodiment in which two hosts are co-evaporated from different evaporation sources to form a light-emitting layer when manufacturing a device, and an embodiment in which a premixture of two host compounds is used.

[0567] In particular, the conditions for preparing the main body of the second light-emitting layer into a premixture have been mentioned above. The two main bodies of the second light-emitting layer in Comparative Examples 9 to 18 and Examples 87 to 122 in Table 17 can be prepared into a premixture as shown in Table 18.

[0568] For the devices manufactured in Comparative Examples 9 to 18 and Examples 87 to 122, the 2 The driving voltage, luminous efficiency, and time to 95% of the initial luminance (LT95) were measured at a current density of . The results are shown in Table 17 below.

[0569] [Table 17]

[0570]

[0571]

[0572]

[0573]

[0574] The results of Table 17 above indicate that the light-emitting layer is formed of two layers, the main body of the first light-emitting layer is a compound according to one embodiment of the present application as a single main body, and the main body of the second light-emitting layer is composed of two anthracene mixed main bodies as a mixed main body-co-evaporated or pre-mixed.

[0575] Comparative Examples 9 and 10 are examples of using H compounds (skeletons substituted with only hydrogen) and D compounds (compounds partially or completely substituted with deuterium) among widely used aryl anthracene compounds to co-evaporate or prepare a premixture for evaporation to form the main body of the second light-emitting layer. Furthermore, Comparative Examples 11, 12, and 13 are examples of using two aryl anthracene compounds and heteroaryl anthracene compounds (one or more of the two is the D compound) to co-evaporate or prepare a premixture for evaporation to form the main body of the second light-emitting layer. Comparative Examples 14, 15, and 16 are examples of using two heteroaryl anthracene compounds (one or more of the two is the D compound) to co-evaporate or prepare a premixture for evaporation to form the main body of the second light-emitting layer.

[0576] Compared with the single host cases of Comparative Examples 1 to 8 in Table 16 above, it can be seen that the use of a mixed host to form a light-emitting layer improves device performance. This can also be confirmed in existing documents KR 2021-0148951 A and KR 2021-0092513 A. In addition, Comparative Examples 17 and 18, like Comparative Example 4 in Table 16, use a boron-based blue dopant, and it can be confirmed that in the case of a mixed host (co-evaporation or pre-mixed manufacturing), characteristic maintenance and device performance improvement are also achieved.

[0577] Examples 87 to 102 are examples that include the features of the present application as described above. By using a compound according to one embodiment of the present application as the main body of the first light-emitting layer, the main body of the second light-emitting layer is formed by co-evaporation (1:1 weight ratio) of a combination of various anthracene (aryl or heteroaryl series, one of the two is a D compound substituted with deuterium) compounds, and it can be observed that compared with Comparative Examples 9 to 18, very excellent voltage and efficiency characteristics are exhibited, and the lifespan can also be improved.

[0578] In Examples 103 to 106, the main body of the second light-emitting layer is different from that of Examples 87 to 102, and the device is made by co-evaporation of D compounds in which two main bodies are both substituted with deuterium, and the lifespan is increased by 15% on average compared with Examples 92, 87, 95 and 101. In Examples 107 to 110, the device is made by using compounds 1-14 to 1-17, which are deuterated compounds 1-1, 1-2, 1-5 and 1-10 in the first light-emitting layer. As mentioned in the results of Table 16, in the case of the first light-emitting layer formed in contact with the hole regulating layer, further improvement in lifespan can be observed by deuterium substitution.

[0579] Examples 111 to 114 are devices produced by changing the host co-evaporation method of the second light-emitting layer of Examples 107 to 110 to a method of forming a premix of two hosts and then evaporating them in one evaporation source. The formation conditions of the premix are implemented as described herein, and due to the uniform mixing effect of molecular units, the device performance of the co-evaporation device is maintained or stably improved.

[0580] Examples 115 to 118 are cases where BD2 (boron-based blue dopant) is applied to one or both of the two light-emitting layers and a premixed main body is applied. It can be seen that compared with the pyrene dopant, high efficiency is maintained while also maintaining the advantages of the premixed main body.

[0581] Examples 119 to 122 are cases where the ratio of the two compounds in the premix of the second light-emitting layer in Examples 115 to 118 is changed and then produced and evaporated to form a main body, showing that the advantages and disadvantages of the two compounds can be reflected in the device by adjusting the ratio.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, R1 to R 10 Any one of them is a part that binds to L1, and the others are the same or different and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or are combined with adjacent groups to form a substituted or unsubstituted ring, L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group, Ar1 is substituted or unsubstituted benzo substituted or unsubstituted dibenzo base, x is 1 or 2, m is 0 to 3. When m is 2 or more, two or more L1 are the same or different from each other. y is 1 or 2. When y is 2, two Ar1s are the same as or different from each other.

2. The compound according to claim 1, wherein The chemical formula 1 is the following chemical formula 1-A: [Chemical Formula 1-A] In the chemical formula 1-A, R1 to R 10 , L1, x, m and y are defined the same as those in the chemical formula 1, R 101 To R 114 Any one of them is a portion that binds to L1, and the others are the same as or different from each other and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or are combined with adjacent groups to form a substituted or unsubstituted ring.

3. The compound according to claim 1, wherein The chemical formula 1 is the following chemical formula 1-B: [Chemical Formula 1-B] In the chemical formula 1-B, R1 to R 10 , L1, x, m and y are defined the same as those in the chemical formula 1, R 101 To R 116 Any one of them is a portion that binds to L1, and the others are the same as or different from each other and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic, or are combined with adjacent groups to form a substituted or unsubstituted ring.

4. The compound according to claim 1, wherein The Chemical Formula 1 contains at least one deuterium.

5. The compound according to claim 1, wherein The deuterium substitution rate of the Chemical Formula 1 is 40% to 99%.

6. The compound according to claim 1, wherein The chemical formula 1 is any one selected from the following compounds:

7. The compound according to claim 1, wherein The chemical formula 1 is any one selected from the following compounds:

8. An organic light emitting device, comprising: an anode, a cathode, a first light-emitting layer disposed between the anode and the cathode, and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, The first light-emitting layer comprises the compound according to any one of claims 1 to 7, The second light-emitting layer comprises at least one of the following compounds of Chemical Formula 2 and Chemical Formula 3: [Chemical formula 2] In the chemical formula 2, At least one of R11 to R20 is bonded to the * site of the following chemical formula 2-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group, [Chemical formula 2-1] L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, Ar2 is a substituted or unsubstituted aryl group, p is an integer from 1 to 3, [Chemical formula 3] In the chemical formula 3, At least one of Y1 to Y10 is bonded to the * site of the following chemical formula 3-1, and the others are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted silyl group, [Chemical formula 3-1] A and B are the same or different from each other, and are each independently a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle, L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group, q is an integer from 1 to 3.

9. The organic light emitting device according to claim 8, wherein: The first light-emitting layer comprises the compound as a host of the first light-emitting layer, The second light-emitting layer includes at least one of the compound of Chemical Formula 2 and the compound of Chemical Formula 3 as a host of the second light-emitting layer.

10. The organic light emitting device according to claim 9, wherein: The first light-emitting layer and the second light-emitting layer each further include a dopant, and the dopant includes a fluorescent dopant.

11. The organic light emitting device according to claim 10, wherein: The fluorescent dopant includes one or more selected from pyrene compounds and non-pyrene compounds.

12. The organic light emitting device according to claim 11, wherein: The non-pyrene-based compounds include boron-based compounds.

13. The organic light emitting device according to claim 8, wherein: The second light emitting layer includes the compound of Chemical Formula 2 or the compound of Chemical Formula 3.

14. The organic light emitting device according to claim 8, wherein: The second light emitting layer includes the compound of Chemical Formula 2 and the compound of Chemical Formula 3.

15. The organic light emitting device according to claim 8, wherein: The deuterium substitution rates of Chemical Formula 2 and Chemical Formula 3 are each 40% to 99%.

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