Compound and organic light-emitting device comprising same

Abstract

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

Description

Technical Field

[0001] This application claims the priority of Korean Patent Application No. 10-2023-0078253 filed with the Korean Patent Office on June 19, 2023 and Korean Patent Application No. 10-2024-0070909 filed with the Korean Patent Office on May 30, 2024, the entire contents of which are incorporated into this specification.

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

[0003] An organic light-emitting device has a structure in which an organic thin film is arranged between two electrodes. When a voltage is applied to an organic light-emitting device of such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form pairs, and then quenched and emit light. The organic thin film may be composed of a single layer or multiple layers as required.

[0004] As substances used in organic light-emitting devices, pure organic substances or coordination compounds of organic substances and metals to form complexes occupy the majority, and can be divided into hole injection substances, hole transport substances, luminescent substances, electron transport substances, electron injection substances, etc. according to their uses. Here, as hole injection substances or hole transport substances, organic substances with p-type properties are mainly used, that is, organic substances that are easily oxidized and have an electrochemically stable state when oxidized. On the other hand, as electron injection substances or electron transport substances, organic substances with n-type properties are mainly used, that is, organic substances that are easily reduced and have an electrochemically stable state when reduced. As light-emitting layer substances, substances with both p-type properties and n-type properties are preferred, that is, substances with stable forms in both oxidized and reduced states, and substances with high luminous efficiency that convert excitons generated by the recombination of holes and electrons in the light-emitting layer into light when formed are preferably used.

[0005] In order to improve the performance, lifespan or efficiency of organic light emitting devices, there is a continuous demand for the development of materials for organic thin films.

[0006] Prior art literature

[0007] Patent Literature

[0008] Korean Patent Publication No. 2016-0132822 Summary of the invention

[0009] Technical issues

[0010] The present specification provides a compound and an organic light-emitting device including the same.

[0011] Solution to the problem

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

[0013] [Chemical formula 1]

[0014]

[0015] In the above chemical formula 1,

[0016] R1 to R3 are the same as or different from each other, and are each independently hydrogen or deuterium,

[0017] L1 and L4 are the same as or different from each other, and are each independently a direct bond, an arylene group substituted or unsubstituted by deuterium, or a heteroarylene group substituted or unsubstituted by deuterium,

[0018] L2 and L3 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,

[0019] Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heteroaryl group,

[0020] Ar3 is a substituted or unsubstituted polycyclic aryl group, or a substituted or unsubstituted heteroaryl group,

[0021] l2 and l3 are each an integer from 1 to 3. When l2 is 2 or more, two or more L2s are the same or different from each other. When l3 is 2 or more, two or more L3s are the same or different from each other.

[0022] r2 is an integer from 1 to 4. When r2 is 2 or more, two or more R2s are the same or different from each other. r3 is an integer from 1 to 3. When r3 is 2 or more, two or more R3s are the same or different from each other.

[0023] Another embodiment of the present specification provides an organic light-emitting device, comprising: a first electrode; a second electrode; and one or more organic layers, the organic layers comprising a light-emitting layer disposed between the first electrode and the second electrode, and one or more of the organic layers comprising the compound of the chemical formula 1.

[0024] Effects of the Invention

[0025] The compound according to one embodiment of the present specification can be used as a material of an organic layer of an organic light-emitting device, and by using the compound, improved efficiency, lower driving voltage, and / or improved lifespan characteristics can be achieved in the organic light-emitting device.

[0026] In particular, when the compound of the present invention is used in a hole injection layer, a hole transport layer or an electron blocking layer, the driving voltage of the device can be reduced, the efficiency of the device can be increased, and the life of the device can be prolonged. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 and 2 Organic light emitting devices according to several embodiments of the present specification are illustrated.

[0028] Explanation of symbols

[0029] 1: Substrate

[0030] 2: First electrode

[0031] 3: Luminous layer

[0032] 4: Second electrode

[0033] 5: Hole injection layer

[0034] 6: Hole transport layer

[0035] 7: Electron blocking layer

[0036] 8: Hole blocking layer

[0037] 9: Electron injection and transport layer DETAILED DESCRIPTION

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

[0039] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0040] [Chemical formula 1]

[0041]

[0042] In the above chemical formula 1,

[0043] R1 to R3 are the same as or different from each other, and are each independently hydrogen or deuterium,

[0044] L1 and L4 are the same as or different from each other, and are each independently a direct bond, an arylene group substituted or unsubstituted by deuterium, or a heteroarylene group substituted or unsubstituted by deuterium,

[0045] L2 and L3 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,

[0046] Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heteroaryl group,

[0047] Ar3 is a substituted or unsubstituted polycyclic aryl group, or a substituted or unsubstituted heteroaryl group,

[0048] l2 and l3 are each an integer from 1 to 3. When l2 is 2 or more, two or more L2s are the same or different from each other. When l3 is 2 or more, two or more L3s are the same or different from each other.

[0049] r2 is an integer from 1 to 4. When r2 is 2 or more, two or more R2s are the same or different from each other. r3 is an integer from 1 to 3. When r3 is 2 or more, two or more R3s are the same or different from each other.

[0050] The compound according to one embodiment of the present specification is represented by the above Chemical Formula 1. When the carbon atom numbers of the phenanthryl group are indicated as shown below, the compound of the above Chemical Formula 1 includes specific substituents at the 2nd and 9th positions of the phenanthryl group.

[0051] In addition, the HOMO and LUMO energies of the compound may be appropriately adjusted according to adjusting the conjugation length of the compound of the above Chemical Formula 1.

[0052] Therefore, when the compound of Chemical Formula 1 is applied to an organic light-emitting device, the organic light-emitting device may exhibit the effects of low voltage, high efficiency and / or long life.

[0053]

[0054] In the present specification, when a part is indicated to “include / comprise” a certain component, unless there is a particular description to the contrary, it means that other components may be further included, rather than excluding other components.

[0055] In the present specification, when it is mentioned that a certain member is located “on” another member, it includes not only a case where the certain member is in contact with the other member but also a case where other members are present between the two members.

[0056] 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. In 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.

[0057] In this specification, "or / or" means inclusive "or / or" rather than exclusive "or / or". For example, condition A or B satisfies any of the following: A is true (or exists), B is false (or does not exist); A is false (or does not exist), B is true (or exists); A and B are both true (or exist).

[0058] In this specification, the meaning of specific substance A contained in layer B includes both i) the case where one or more substances A are contained in one layer of 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 of layer B.

[0059] In this specification, a specific substance A is contained in layer C or layer D, which means all of the following situations: i) contained in one or more layers of one or more layers C, or ii) contained in one or more layers of one or more layers D, or iii) contained in one or more layers C and one or more layers D, respectively.

[0060] In the present specification, "-----" each represents a site that is connected to another substituent or a linking part.

[0061] In the present specification, examples of substituents are described below, but are not limited thereto.

[0062] The term "substituted" mentioned above means that the hydrogen atom bonded to the carbon atom of the compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0063] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, a phosphine oxide group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The alkylene group may be substituted with one or more substituents selected from the group consisting of alkenyl, silyl, boronyl, amine, aryl, and heterocyclic groups, or may be substituted with a substituent formed by connecting two or more substituents selected from the group consisting of the above-mentioned substituents, or may not have any substituent. For example, the "substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent formed by connecting two phenyl groups.

[0064] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a silyl group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0065] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, alkyl, aryl, and heterocyclic groups, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0066] Examples of the above substituents are described below, but are not limited thereto.

[0067] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0068] In the present specification, the silyl group can be represented by the chemical formula -SiYaYbYc, wherein Ya, Yb and Yc can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0069] In this specification, the boron group can be represented by the chemical formula -BYdYe, and the above-mentioned Yd and Ye can each be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The above-mentioned boron group specifically includes trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, etc., but is not limited thereto.

[0070] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. In one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. In another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. In another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0071] In this specification, the alkoxy group can be straight chain, branched 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 can be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropyloxy 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, etc., but it is not limited thereto.

[0072] In the present specification, the above-mentioned explanations about the alkyl group can be applied to the alkyl group in the alkylthio group and the alkylsulfonyl group.

[0073] In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but preferably 2 to 40. In one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. In another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. In another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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.

[0074] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0075] In the present specification, the amino group is -NH2, and the above-mentioned amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the above-mentioned substituted amino group is not particularly limited, but is preferably 1 to 30. In one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 20. In one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 10. As specific examples of substituted amino groups, there are methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.

[0076] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. In one embodiment, the carbon number of the aryl group is 6 to 30. In one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.

[0077] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0078] When the fluorenyl group is substituted, it may be Isospirofluorenyl; (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and the like substituted fluorenyl, but the present invention is not limited thereto.

[0079] In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group, the arylthio group and the arylsulfonyl group.

[0080] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. In one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. In one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like, but are not limited thereto.

[0081] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0082] In this specification, an aliphatic hydrocarbon ring refers to a ring that is not an aromatic ring and is composed only of carbon and hydrogen atoms. The number of carbon atoms in the aliphatic hydrocarbon ring is not particularly limited, but preferably the number of carbon atoms is 3 to 60. In one embodiment, the number of carbon atoms in the aliphatic hydrocarbon ring is 3 to 30. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc., but are not limited thereto.

[0083] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. The number of carbon atoms in the aromatic hydrocarbon ring is not particularly limited, but preferably the number of carbon atoms is 6 to 60. In one embodiment, the number of carbon atoms in the aliphatic hydrocarbon ring is 6 to 30. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as the aryl group.

[0084] 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.

[0085] In the present specification, a heteroarylene group refers to a group having two bonding positions on a heteroaryl group, that is, a divalent group. The above description of the heteroaryl group is applicable to these groups except that they are each a divalent group.

[0086] In this specification, D represents deuterium.

[0087] In this manual, [] Dn It means that the structure in the brackets contains deuterium. In this case, D is deuterium and n is the number of deuterium. That is, Dn represents the number of deuterium contained in the structure in the brackets, and its value is an integer. For example, 1≤Dn≤33 means that 1 to 33 deuteriums are contained. As an example, the following structure contains 1 to 33 deuteriums.

[0088]

[0089] In the present specification, hydrogen means hydrogen, deuterium or tritium.

[0090] In one embodiment of the present specification, the part without a substituent in the above Chemical Formula 1 may be substituted with hydrogen, deuterium or tritium.

[0091] In this specification, unless otherwise defined, all technical terms and scientific terms used in this specification have the same meaning as those generally understood by those skilled in the art. Methods and materials similar or equivalent to the description in this specification can be used for the implementation or test of embodiments of the present invention, but suitable methods and materials are described later. All publications, patent applications, patents and other references mentioned in this specification are included in this specification as a whole as a reference, and when conflicting, 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.

[0092] Next, the compound of the above Chemical Formula 1 will be described in detail.

[0093] In one embodiment of the present specification, L1 is a direct bond, an arylene group which may be substituted by deuterium, or a heteroarylene group which may be substituted by deuterium.

[0094] In one embodiment of the present specification, L1 is a direct bond, an arylene group having 6 to 30 carbon atoms which may be substituted with deuterium or an arylene group having 2 to 30 carbon atoms which may be substituted with deuterium or an heteroarylene group having 2 to 30 carbon atoms which may be substituted with deuterium or an unsubstituted heteroarylene group.

[0095] In one embodiment of the present specification, L1 is a direct bond, a phenylene group which may be substituted by deuterium, a biphenylene group which may be substituted by deuterium, or a naphthylene group which may be substituted by deuterium.

[0096] In one embodiment of the present specification, the above-mentioned L1 is a direct bond, a phenylene group, a biphenylene group, or a naphthylene group.

[0097] In one embodiment of the present specification, L2 and L3 are the same as or different from each other, and are each independently 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.

[0098] In one embodiment of the present specification, L2 and L3 are the same as or different from each other, and are each independently a direct bond; an arylene group substituted or unsubstituted by one or more selected from deuterium, an alkyl group, and an aryl group; or a heteroarylene group substituted or unsubstituted by one or more selected from deuterium, an alkyl group, and an aryl group.

[0099] In one embodiment of the present specification, L2 and L3 are the same as or different from each other and are independently a direct bond; an arylene group having 6 to 30 carbon atoms and substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl groups; or a heteroarylene group having 2 to 30 carbon atoms and substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl groups.

[0100] In one embodiment of the present specification, the above-mentioned L2 and L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent fluorenyl group, a substituted or unsubstituted divalent spirobifluorenyl group, or a substituted or unsubstituted divalent phenanthryl group.

[0101] In one embodiment of the present specification, the above-mentioned L2 and L3 are the same as or different from each other and are each independently a direct bond; a phenylene group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; a biphenylene group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; a terphenylene group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; a naphthyl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; a divalent fluorenyl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; a divalent spirobifluorenyl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; or a divalent phenanthrenyl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group.

[0102] In one embodiment of the present specification, the above-mentioned L2 and L3 are the same as or different from each other, and are each independently a direct bond, a phenylene group, a biphenylene group, a terphenylene group, a naphthyl group, a divalent fluorenyl group substituted or unsubstituted with one or more selected from an alkyl group and an aryl group, a divalent spirobifluorenyl group, or a divalent phenanthryl group.

[0103] In one embodiment of the present specification, L4 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.

[0104] In one embodiment of the present specification, the above-mentioned L4 is a direct bond.

[0105] In one embodiment of the present specification, the above R1 is hydrogen or deuterium.

[0106] In one embodiment of the present specification, R2 and R3 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0107] In one embodiment of the present specification, Ar3 is a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0108] In one embodiment of the present specification, Ar3 is a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.

[0109] In one embodiment of the present specification, Ar3 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0110] In one embodiment of the present specification, the Ar3 is a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthrenyl group.

[0111] In one embodiment of the present specification, the Ar3 is a naphthyl group or a phenanthrenyl group.

[0112] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted condensed ring group of an aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aliphatic hydrocarbon ring having 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0113] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other and are independently hydrogen; deuterium; an alkyl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; an aryl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; or a heteroaryl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group.

[0114] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are independently substituted or unsubstituted propyl; substituted or unsubstituted butyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted triphenylene; substituted or unsubstituted fluorenyl with one or more selected from deuterium, alkyl and aryl; substituted or unsubstituted spirobifluorenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenyl; substituted or unsubstituted carbazolyl; or R10 to R13 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0115] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other and are independently substituted or unsubstituted propyl by one or more selected from deuterium, alkyl and aryl; substituted or unsubstituted butyl by one or more selected from deuterium, alkyl and aryl; substituted or unsubstituted phenyl by one or more selected from deuterium, alkyl and aryl; substituted or unsubstituted biphenyl by one or more selected from deuterium, alkyl and aryl; substituted or unsubstituted terphenyl by one or more selected from deuterium, alkyl and aryl; substituted or unsubstituted naphthyl by one or more selected from deuterium, alkyl and aryl; phenanthryl substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl; triphenylene substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl; fluorenyl substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl; spirobifluorenyl substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl; dibenzofuranyl substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl; dibenzothienyl substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl; carbazolyl substituted or unsubstituted by one or more selected from deuterium, alkyl and aryl; or R10 to R13 are the same as or different from each other, and are each independently an alkyl group or an aryl group.

[0116] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently any one of the following structures.

[0117]

[0118] In the above structure,

[0119] R10 to R16 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

[0120] The above structure is substituted or unsubstituted by one or more substituents selected from deuterium, alkyl and aryl,

[0121] is a portion bonded to Chemical Formula 1.

[0122] In one embodiment of the present specification, the structures exemplified by Ar1 and Ar2 may be substituted or unsubstituted by one or more substituents selected from an alkyl group having 1 to 30 carbon atoms and an aryl group having 6 to 30 carbon atoms.

[0123] In one embodiment of the present specification, the structures exemplified by Ar1 and Ar2 are substituted or unsubstituted by one or more substituents selected from the group consisting of a methyl group, a tert-butyl group, and a phenyl group.

[0124] In one embodiment of the present specification, the above R10 to R16 are the same as or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

[0125] In one embodiment of the present specification, the above R10 to R16 are the same as or different from each other, and are each independently a methyl group or a phenyl group.

[0126] In one embodiment of the present specification, the compound is selected from the following structures.

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157] In the above structure, Dn is the number of deuterium contained in the compound.

[0158] In one embodiment of the present specification, the compound represented by the above Chemical Formula 1 can be produced according to the following reaction formula.

[0159] [Reaction formula]

[0160]

[0161] In the above reaction formula, the definitions of R1 to R3, L1 to L4, l2, l3, r2, r3 and Ar1 to Ar3 are the same as those in the above Chemical Formula 1.

[0162] In the above reaction formula, X is a halogen group. Specifically, X is Cl, Br or I.

[0163] In this specification, various substituents are introduced into the core structure as described above, so that compounds with various energy band gaps can be synthesized. In addition, in the present invention, various substituents are introduced into the core structure of the structure as described above, so that the HOMO and LUMO energy levels of the compound can also be adjusted.

[0164] In addition, by introducing various substituents into the core structure of the structure described above, a compound having the inherent characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection materials, hole transport materials, electron blocking materials, luminescent materials, and electron transport materials used in the manufacture of organic light-emitting devices into the above core structure, a material that meets the conditions required in each organic layer can be synthesized.

[0165] Next, the organic light-emitting device will be described in detail.

[0166] The organic light-emitting device according to the present specification includes a first electrode; a second electrode; and one or more organic layers including a light-emitting layer disposed between the first electrode and the second electrode, wherein one or more of the organic layers includes the compound of Chemical Formula 1.

[0167] The organic light-emitting device of the present specification may be manufactured using the above-mentioned compounds to form one or more organic layers, and may otherwise be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0168] The above compounds can be formed into an organic layer by not only vacuum evaporation method but also solution coating method when manufacturing organic light-emitting devices. Here, the so-called solution coating method refers to spin coating method, dip coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0169] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the device can be manufactured as follows: a physical vapor deposition method (PVD: physical vapor deposition) such as sputtering or e-beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0170] In one embodiment of the present specification, the organic layer may be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, when the organic light-emitting device includes a plurality of organic layers, the organic layer may be a multi-layer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number or a larger number of organic layers.

[0171] The organic layer may be formed of the same substance or different substances. In addition, the organic layer may be formed using various polymer materials by a vapor deposition method and / or a solution process.

[0172] In one embodiment of the present specification, a plurality of organic layers are included between the first electrode and the light-emitting layer, and the organic layer closer to the light-emitting layer among the plurality of organic layers includes the compound.

[0173] In one embodiment of the present specification, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

[0174] In one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer or an electron blocking layer, and the hole injection layer, the hole transport layer or the electron blocking layer includes the compound.

[0175] In one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.

[0176] In one embodiment of the present specification, the organic layer includes a hole transport layer, and the hole transport layer includes the compound.

[0177] In one embodiment of the present specification, the organic layer includes a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron blocking layer or the hole transport layer includes the compound.

[0178] In one embodiment of the present specification, the organic layer includes a light-emitting layer. In this case, the light-emitting layer may or may not include the compound of Chemical Formula 1.

[0179] In one embodiment of the present specification, the light-emitting layer includes the above-mentioned compound.

[0180] In one embodiment of the present specification, the light-emitting layer may include the compound as a dopant of the light-emitting layer.

[0181] In one embodiment of the present specification, the light-emitting layer includes the compound as a dopant of the light-emitting layer, and may further include a host.

[0182] In one embodiment of the present specification, the light-emitting layer includes the compound as a dopant of the light-emitting layer, further includes a fluorescent host or a phosphorescent host, and may further include other organic compounds, metals or metal compounds as dopants.

[0183] In one embodiment of the present specification, the light-emitting layer includes the compound as a dopant of the light-emitting layer and further includes a fluorescent host or a phosphorescent host, and an iridium (Ir)-based dopant may be used together.

[0184] In one embodiment of the present specification, the light-emitting layer may contain the compound as a host of the light-emitting layer.

[0185] In one embodiment of the present specification, the light-emitting layer contains the compound as a host of the light-emitting layer, and may further contain a dopant.

[0186] In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer arranged between the first electrode and the second electrode, and a single-layer organic layer is further included between the light-emitting layer and the first electrode, and the organic layer includes the compound of the above chemical formula 1.

[0187] In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer arranged between the first electrode and the second electrode, and a plurality of organic layers are included between the light-emitting layer and the first electrode, and at least one layer of the organic layers contains the compound.

[0188] In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer arranged between the first electrode and the second electrode, and the light-emitting layer and the first electrode also include one or more of a hole injection layer, a hole transport layer and an electron blocking layer, and one or more of the hole injection layer, the hole transport layer and the electron blocking layer contain the above-mentioned compound.

[0189] In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer arranged between the first electrode and the second electrode, and the first electrode and the light-emitting layer include a hole injection layer, a hole transport layer and an electron blocking layer, and at least one of the hole injection layer, the hole transport layer and the electron blocking layer contains the above-mentioned compound.

[0190] For example, an organic light-emitting device according to one embodiment of the present specification has a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and a second electrode are sequentially arranged, and at least one of the hole injection layer, hole transport layer, and electron blocking layer contains the above-mentioned compound.

[0191] In one embodiment of the present specification, the organic light-emitting device is a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and a second electrode are stacked in sequence, and the hole injection layer, the hole transport layer or the electron blocking layer contains the above-mentioned compound.

[0192] In one embodiment of the present specification, another organic layer may be included between the light-emitting layer and the second electrode. For example, the light-emitting layer and the second electrode may include at least one of a hole blocking layer, an electron injection layer, an electron transport layer, and a layer that simultaneously performs electron injection and transport.

[0193] In one embodiment of the present specification, the organic light-emitting device is a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are stacked in sequence, and at least one of the hole injection layer, hole transport layer and electron blocking layer contains the above-mentioned compound.

[0194] In one embodiment of the present specification, the organic light-emitting device is a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are stacked in sequence, and the hole injection layer, the hole transport layer or the electron blocking layer contains the above-mentioned compound.

[0195] In one embodiment of the present specification, the organic light-emitting device is a structure in which a first electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a second electrode are stacked in sequence, and the hole transport layer or the electron blocking layer contains the above-mentioned compound.

[0196] In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

[0197] In another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0198] For example, the structure of the organic light-emitting device of the present specification may have the following Figure 1 and 2 The structure shown is not limited thereto.

[0199] Figure 1 An example of an organic light-emitting device composed of a substrate 1 , a first electrode 2 , a light-emitting layer 3 , and a second electrode 4 is shown.

[0200] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a second electrode 4.

[0201] Specifically, in addition to the structures explicitly shown in the above figures, the above organic light-emitting device may have a stacked structure as shown below, but is not limited thereto.

[0202] (1) Anode / hole transport layer / light-emitting layer / cathode

[0203] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0204] (3) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0205] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0206] (5) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0207] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0208] (7) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0209] (8) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0210] (9) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0211] (10) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0212] (11) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0213] (12) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0214] (13) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0215] (14) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0216] (15) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0217] In one embodiment of the present specification, the above-mentioned “electron transport layer / electron injection layer” may be replaced with “electron injection and transport layer” or “a layer that simultaneously injects and transports electrons”.

[0218] In one embodiment of the present specification, the above-mentioned “hole injection layer / hole transport layer” may be replaced with “hole injection and transport layer” or “layer that simultaneously performs hole injection and transport”.

[0219] The anode is an electrode for injecting holes. As the anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0220] The cathode is an electrode for injecting electrons. As the cathode material, in order to facilitate the injection of electrons into the organic layer, a material with a small work function is preferably used. Specific examples of cathode materials that can be used in the present invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0221] The hole injection layer can play a role in making the injection of holes from the anode to the light-emitting layer smooth. The hole injection material is a material that can well receive holes from the anode at a low voltage, and the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrines, oligothiophenes, arylamine compounds, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, perylene compounds, benzonitrile compounds, anthraquinone and polyaniline and polythiophene conductive polymers, but are not limited to these.

[0222] Specifically, arylamine compounds, quinoxaline compounds, and benzonitrile compounds can be used in the hole injection layer. More specifically, quinoxaline compounds can be used, but the present invention is not limited thereto.

[0223] In one embodiment of the present specification, the hole injection layer includes a compound of the following chemical formula HI-A.

[0224] [Chemical formula HI-A]

[0225]

[0226] In the above chemical formula HI-A,

[0227] Rh1 To R h6 are the same as or different from each other, and are each independently hydrogen, deuterium, cyano, substituted or unsubstituted amine, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.

[0228] In one embodiment of the present specification, the above R h1 To R h6 Each is a cyano group.

[0229] In one embodiment of the present specification, the chemical formula HI-A is the following structure.

[0230]

[0231] The thickness of the hole injection layer can be 1nm to 150nm. When the thickness of the hole injection layer is more than 1nm, it has the advantage of preventing the hole injection characteristics from being reduced, and when it is less than 150nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of holes when the thickness of the hole injection layer is too thick.

[0232] The hole transport layer can play a role in making the hole transport smooth. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is suitable for materials with high hole mobility. Specific examples of hole transport materials include compounds of the above chemical formula 1, aromatic amine compounds, carbazole compounds, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited to these. Specifically, the compound of the above chemical formula 1 or the carbazole compound substituted with an aromatic amine group can be used in the hole transport layer, but is not limited to this. More specifically, the hole transport layer can use the compound of the above chemical formula 1 or the following HT-A compound.

[0233] [Chemical formula HT-A]

[0234]

[0235] In the above chemical formula HT-A,

[0236] Lx1 and Lx2 are the same or different from each other, and are each independently a directly bonded, or substituted or unsubstituted arylene group,

[0237] Rx1 to Rx5 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.

[0238] In one embodiment of the present specification, Lx1 and Lx2 are the same as or different from each other, and are each independently a substituted or unsubstituted arylene group.

[0239] In one embodiment of the present specification, Lx1 and Lx2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0240] In one embodiment of the present specification, Lx1 and Lx2 are the same as or different from each other, and are each independently an arylene group.

[0241] In one embodiment of the present specification, Lx1 and Lx2 are the same as or different from each other, and are each independently a phenylene group, a biphenylene group, or a naphthylene group.

[0242] In one embodiment of the present specification, each of Lx1 and Lx2 is a phenylene group.

[0243] In one embodiment of the present specification, the above Rx1 to Rx5 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group.

[0244] In one embodiment of the present specification, the above Rx1 to Rx5 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0245] In one embodiment of the present specification, the above Rx1 to Rx5 are the same as or different from each other, and are each independently an aryl group.

[0246] In one embodiment of the present specification, the above Rx1 to Rx5 are the same as or different from each other, and are each independently a phenyl group or a naphthyl group.

[0247] In one embodiment of the present specification, the chemical formula HT-A is the following structure.

[0248]

[0249] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. A phenanthrene compound or a material known in the art may be used in the electron blocking layer. Specifically, the compound of the chemical formula 1 or a compound in which L1 in the chemical formula 1 is directly bonded may be used in the electron blocking layer.

[0250] In one embodiment of the present specification, a hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and the hole buffer layer may include a hole injection or transport material known in the technical field.

[0251] In one embodiment of the present specification, the light-emitting layer can emit red, green or blue light and can be formed of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, preferably a material with high quantum efficiency for fluorescence or phosphorescence. For example, the light-emitting material includes 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0252] As the main material of the light-emitting layer, there are aromatic fused ring derivatives or heterocyclic compounds. For example, as aromatic fused ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Specifically, as the host of the light-emitting layer, anthracene derivatives can be used, but not limited to them.

[0253] In one embodiment of the present specification, the host is represented by the following chemical formula HA.

[0254] [Chemical formula HA]

[0255]

[0256] In the above chemical formula HA,

[0257] L h1 and L h2 are the same as or different from each other and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0258] R h1 and R h2 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,

[0259] R h3 is hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0260] r h3 is an integer from 1 to 8, and the above r h3When it is 2 or more, 2 or more R h3 The same as or different from each other.

[0261] In one embodiment of the present specification, the above L h1 and L h2 are the same as or different from each other, and are each independently a direct bond or an arylene group.

[0262] In one embodiment of the present specification, the above L h1 and L h2 Each is a direct bond.

[0263] In one embodiment of the present specification, the above R h1 and R h2 The same as or different from each other, and each independently is a substituted or unsubstituted aryl group.

[0264] In one embodiment of the present specification, the above R h1 and R h2 The same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0265] In one embodiment of the present specification, the above R h1 and R h2 The same as or different from each other, and each independently is an aryl group.

[0266] In one embodiment of the present specification, the above R h1 and R h2 The same as or different from each other, and each independently is phenyl, biphenyl or naphthyl.

[0267] In one embodiment of the present specification, the above R h1 and R h2 Each is a naphthyl group.

[0268] In one embodiment of the present specification, the above R h3 is hydrogen or deuterium.

[0269] In one embodiment of the present specification, the chemical formula HA is the following structure.

[0270]

[0271] When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium, face-tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum) can be used, but are not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic can be used; or fluorescent materials such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), pyrene-based compounds, PFO-based polymers, PPV-based polymers can be used, but are not limited to these. Specifically, as the above-mentioned dopant, a pyrene-based compound can be used, but is not limited to this.

[0272] In one embodiment of the present specification, the light-emitting layer includes a dopant, and the dopant includes a fluorescent dopant.

[0273] In one embodiment of the present specification, the fluorescent dopant includes one or more selected from pyrene-based compounds and non-pyrene-based compounds.

[0274] In one embodiment of the present specification, the fluorescent dopant is a pyrene compound or a non-pyrene compound. The pyrene compound and the non-pyrene compound can be used without limitation as long as they are compounds used in the technical field.

[0275] In one embodiment of the present specification, the pyrene-based compound is represented by the following chemical formula DA.

[0276] [Chemical formula DA]

[0277]

[0278] In the above chemical formula DA,

[0279] R f1 and R f2 are the same as or different from each other and are each independently hydrogen, deuterium, substituted or unsubstituted amine, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl,

[0280] rfa and rfb are each an integer of 1 to 5. When rfa and rfb are 2 or more, the substituents in the respective brackets are the same as or different from each other.

[0281] In one embodiment of the present specification, the above R f1 and R f2 The same as or different from each other, and each independently is a substituted or unsubstituted amino group.

[0282] In one embodiment of the present specification, the chemical formula DA is the following chemical formula DA-1.

[0283] [Chemical formula DA-1]

[0284]

[0285] In the above chemical formula DA-1,

[0286] R f3 To R f6 The same as or different from each other, and each independently is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0287] In one embodiment of the present specification, the chemical formula DA is the following chemical formula DA-2.

[0288] [Chemical formula DA-2]

[0289]

[0290] In the above chemical formula DA-2,

[0291] R f3 To R f6 The same as or different from each other, and each independently is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0292] In one embodiment of the present specification, the above R f3 To R f6 The same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.

[0293] In one embodiment of the present specification, the above R f3 To R f6 The same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group, or a substituted or unsubstituted dibenzofuranyl group.

[0294] In one embodiment of the present specification, the chemical formula DA is the following structure.

[0295]

[0296] The hole blocking layer is a layer that blocks holes from reaching the cathode and can be formed under the same conditions as the hole injection layer. Specific examples of hole blocking materials include Oxadiazole derivatives, triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but not limited thereto. Specifically, triazine derivatives can be used, but not limited thereto.

[0297] The above-mentioned electron transport layer can play a role in making the transmission of electrons smooth. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and is suitable for materials with high electron mobility. For example, as the above-mentioned electron transport material, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The thickness of the electron transport layer can be 1nm to 50nm. When the thickness of the electron transport layer is more than 1nm, it has the advantage of preventing the electron transport characteristics from being reduced. When it is less than 50nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.

[0298] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. For example, the electron injection material includes fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0299] 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.

[0300] The electron transport layer and the electron injection layer may be formed of a single layer. For example, the electron injection material and the electron transport material may be simultaneously vacuum-deposited, or a material having both electron injection and transport effects may be vacuum-deposited to form the electron injection and transport layer.

[0301] In one embodiment of the present specification, the electron injection and transport layer includes a compound represented by the following chemical formula ET-A, but is not limited thereto.

[0302] [Chemical formula ET-A]

[0303]

[0304] In the above chemical formula ET-A,

[0305] At least one of Z11 to Z13 is N, and the rest are CH,

[0306] At least one of Z21 to Z23 is N, and the others are CH,

[0307] L601 and L602 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0308] Ar601 to Ar604 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.

[0309] In one embodiment of the present specification, L601 and L602 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.

[0310] In one embodiment of the present specification, L601 and L602 are the same as or different from each other, and are each independently an arylene group.

[0311] In one embodiment of the present specification, L601 and L602 are phenylene groups.

[0312] In one embodiment of the present specification, Ar601 to Ar604 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.

[0313] In one embodiment of the present specification, the above-mentioned Ar601 to Ar604 are the same as or different from each other, and are each independently an aryl group.

[0314] In one embodiment of the present specification, Ar601 to Ar604 are phenyl groups.

[0315] In one embodiment of the present specification, the chemical formula ET-A is represented by the following compound.

[0316]

[0317] In one embodiment of the present specification, the electron injection and transport layer may further include a metal complex. Examples of the metal complex include, but are not limited to, Al complexes of 8-hydroxyquinoline (Alq3), Liq, metal coordination compounds, etc. For example, the electron injection and transport layer may use triazine derivatives and lithium quinoline (Liq), but are not limited to these.

[0318] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0319] In addition, 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.

[0320] Below, in order to specifically illustrate the present invention, embodiments will be cited and described in detail. However, embodiments according to the present invention can be deformed into various forms, and it is not interpreted that the scope of the present invention is limited to the embodiments described in detail below. The embodiments of the present invention are provided to more completely illustrate this specification to those skilled in the art.

[0321] <Synthesis example>

[0322] Synthesis Example 1. Synthesis of Compound 1

[0323]

[0324] Toluene (200 ml) was added to 9-chloro-2-(naphthalene-1-yl)phenanthrene (20.00 g, 59.03 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine (23.96 g, 60.21 mmol) and sodium tert-butoxide ((NaOtBu)) (7.94 g, 82.64 mmol), followed by heating and stirring for 10 minutes. To the above mixture was added bis(tri-tert-butylphosphine)palladium (BTP) (0.15 g, 0.30 mmol) dissolved in toluene (20 ml), followed by heating and stirring for 1 hour. After the reaction was completed and filtered, the layers were separated using toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain Compound 1 (32.00 g, 77.45% yield). (MS [M+H] + =700)

[0325] Synthesis Example 2. Synthesis of Compound 2

[0326]

[0327] In the above-mentioned Synthesis Example 1, except that bis(4-(naphthalen-1-yl)phenyl)amine (25.38 g, 60.21 mmol) was used instead of N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 2 (33 g, 77.22% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =724)

[0328] Synthesis Example 3. Synthesis of Compound 3

[0329]

[0330] In the above-mentioned Synthesis Example 1, except that 9-chloro-2-(naphthalene-2-yl)phenanthrene (20.00 g, 59.03 mmol) was used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene (20.00 g, 59.03 mmol), the same method as the above-mentioned Synthesis Example 1 was used to obtain Compound 3 (32.00 g, 77.45% yield). (MS [M + H] + =700)

[0331] Synthesis Example 4. Synthesis of Compound 4

[0332]

[0333] In the above-mentioned Synthesis Example 1, except that 9-chloro-2-(naphthalene-2-yl)phenanthrene (20.00 g, 59.03 mmol) and bis(4-(naphthalene-1-yl)phenyl)amine (25.38 g, 60.21 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, compound 4 (32.50 g, 76.05% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =724)

[0334] Synthesis Example 5. Synthesis of Compound 5

[0335]

[0336] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.80 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 5 (27.00 g, 80.04% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =700)

[0337] Synthesis Example 6. Synthesis of Compound 6

[0338]

[0339] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (15.80 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 6 (26.50 g, 78.55% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =700)

[0340] Synthesis Example 7. Synthesis of Compound 7

[0341]

[0342] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-2-yl)-[1,1':4',1"-terphenyl]-4-amine (19.54 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, compound 7 (30.00 g, 80.21% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =776)

[0343] Synthesis Example 8. Synthesis of Compound 8

[0344]

[0345] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and N-(4-(naphthalene-1-yl)phenyl)-[1,1'-biphenyl]-2-amine (18.26 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 8 (28.50 g, 78.84% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =750)

[0346] Synthesis Example 9. Synthesis of Compound 9

[0347]

[0348] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and N-(4-(naphthalene-2-yl)phenyl)-[1,1'-biphenyl]-2-amine (18.26 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 9 (28.50 g, 78.84% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =750)

[0349] Synthesis Example 10. Synthesis of Compound 10

[0350]

[0351] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and 4-(phenanthrene-9-yl)-N-phenylaniline (16.98 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 10 (28.00 g, 80.25% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =724)

[0352] Synthesis Example 11. Synthesis of Compound 11

[0353]

[0354] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (14.03 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 11 (24.50 g, 76.57% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =664)

[0355] Synthesis Example 12. Synthesis of Compound 12

[0356]

[0357] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and 2'-(9H-carbazole-9-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (20.18 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 12 (30.00 g, 78.89% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =789)

[0358] Synthesis Example 13. Synthesis of Compound 13

[0359]

[0360] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-1-amine (16.49 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 13 (27.00 g, 78.47% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =714)

[0361] Synthesis Example 14. Synthesis of Compound 14

[0362]

[0363] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.80 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 14 (26.50 g, 78.55% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =700)

[0364] Synthesis Example 15. Synthesis of Compound 15

[0365]

[0366] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (15.80 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 15 (26.50 g, 78.55% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =700)

[0367] Synthesis Example 16. Synthesis of Compound 16

[0368]

[0369] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-2-yl)-[1,1':4',1"-terphenyl]-4-amine (19.54 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, compound 16 (30.00 g, 80.21% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =776)

[0370] Synthesis Example 17. Synthesis of Compound 17

[0371]

[0372] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and N-(4-(naphthalene-1-yl)phenyl)-[1,1'-biphenyl]-2-amine (18.26 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, compound 17 (28.00 g, 77.46% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =750)

[0373] Synthesis Example 18. Synthesis of Compound 18

[0374]

[0375] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and N-(4-(naphthalene-2-yl)phenyl)-[1,1'-biphenyl]-2-amine (18.26 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 18 (28.00 g, 77.46% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =750)

[0376] Synthesis Example 19. Synthesis of Compound 19

[0377]

[0378] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and 4-(phenanthrene-9-yl)-N-aniline (16.98 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 19 (28.00 g, 80.25% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =724)

[0379] Synthesis Example 20. Synthesis of Compound 20

[0380]

[0381] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and 9,9-dimethyl-N-phenyl-9H-fluorene-2-amine (14.03 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 20 (24.50 g, 76.57% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =664)

[0382] Synthesis Example 21. Synthesis of Compound 21

[0383]

[0384] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and 2'-(9H-carbazol-9-yl)-N-phenyl-[1,1'-biphenyl]-4-amine (20.18 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 21 (30.00 g, 78.89% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =789)

[0385] Synthesis Example 22. Synthesis of Compound 22

[0386]

[0387] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-1-amine (16.49 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 22 (26.50 g, 77.01% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =714)

[0388] Synthesis Example 23. Synthesis of Compound 23

[0389]

[0390] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2,9'-biphenylene (20.00 g, 43.01 mmol) and di([1,1'-biphenyl]-4-yl)amine (14.10 g, 43.87 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 23 (26.00 g, 80.61% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =750)

[0391] Synthesis Example 24. Synthesis of Compound 24

[0392]

[0393] In the above-mentioned Synthesis Example 1, except that 9-(4-chlorophenyl)-2,9'-biphenylene (20.00 g, 43.01 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (14.10 g, 43.87 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 24 (25.00 g, 77.51% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =750)

[0394] Synthesis Example 25. Synthesis of Compound 25

[0395]

[0396] In the above-mentioned Synthesis Example 1, except that 9-(3-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.80 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 25 (26.50 g, 78.55% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =700)

[0397] Synthesis Example 26. Synthesis of Compound 26

[0398]

[0399] In the above-mentioned Synthesis Example 1, except that 9-(3-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and N-(4-(naphthalene-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (18.26 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 26 (28.50 g, 78.84% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =750)

[0400] Synthesis Example 27. Synthesis of Compound 27

[0401]

[0402] In the above-mentioned Synthesis Example 1, except that 9-(3-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.80 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 27 (26.50 g, 78.55% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =700)

[0403] Synthesis Example 28. Synthesis of Compound 28

[0404]

[0405] In the above-mentioned Synthesis Example 1, except that 9-(3-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and N-(4-(naphthalene-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (18.26 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the above-mentioned compound 28 (28.50 g, 78.84% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =750)

[0406] Synthesis Example 29. Synthesis of Compound 29

[0407]

[0408] In the above-mentioned Synthesis Example 1, except that 9-(2-chlorophenyl)-2-(naphthalene-1-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine (19.54 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 29 (28.50 g, 76.20% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =776)

[0409] Synthesis Example 30. Synthesis of Compound 30

[0410]

[0411] In the above-mentioned Synthesis Example 1, except that 9-(2-chlorophenyl)-2-(naphthalene-2-yl)phenanthrene (20.00 g, 48.20 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine (19.54 g, 49.16 mmol) were used instead of 9-chloro-2-(naphthalene-1-yl)phenanthrene and N-([1,1'-biphenyl]-4-yl)-[1,1':4',1"-terphenyl]-4-amine, the compound 30 (28.50 g, 76.20% yield) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =776)

[0412] Synthesis Example 31. Synthesis of Compound 31

[0413]

[0414] Compound 5 (20.0 g, 28.58 mmol) obtained in the above-mentioned synthesis example 5 was added to benzene-D6 (200 ml), and after complete dissolution, trifluoromethanesulfonic acid (CF3SO3H) (1.3 ml, 14.3 mmol) was added and stirred for 25 minutes. After the reaction was completed, dichloromethane was added and the layers were separated to obtain an organic layer. After drying with anhydrous magnesium sulfate (MgSO4), the mixture was filtered. The filtrate was concentrated under reduced pressure and recrystallized with ethyl acetate to obtain compound 31 (16.0 g, 77.86% yield). (MS[M+H] + =719)

[0415] Synthesis Example 32. Synthesis of Compound 32

[0416]

[0417] In the above Synthesis Example 31, Compound 7 (20.0 g, 25.77 mmol) obtained in the above Synthesis Example 7 was used instead of Compound 5. Compound 32 (16.00 g, 77.89% yield) was obtained by the same method as the above Synthesis Example 31. (MS [M+H] + =797)

[0418] Synthesis Example 33. Synthesis of Compound 33

[0419]

[0420] In the above Synthesis Example 31, Compound 14 (20.0 g, 28.58 mmol) obtained in the above Synthesis Example 14 was used instead of Compound 5. Compound 33 (16.00 g, 77.86% yield) was obtained by the same method as the above Synthesis Example 31. (MS [M+H] + =719)

[0421] Synthesis Example 34. Synthesis of Compound 34

[0422]

[0423] In the above Synthesis Example 31, Compound 16 (20.0 g, 25.77 mmol) obtained in the above Synthesis Example 16 was used instead of Compound 5. Compound 34 (16.00 g, 77.89% yield) was obtained by the same method as the above Synthesis Example 31. (MS [M+H] + =797)

[0424] <Experimental Examples and Comparative Examples>

[0425] Experimental Example 1-1

[0426] ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0427] On the ITO transparent electrode prepared in this way, a compound represented by the following chemical formula HAT was applied as A hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 was deposited as a hole transport layer. After vacuum deposition with a thickness of , as an electron blocking layer, the compound 1 prepared in the above-mentioned synthesis example 1 was Next, as a light-emitting layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were added at a weight ratio of 25:1 and at a weight ratio of Next, as a hole blocking layer, a compound represented by the following chemical formula HB1 was deposited in the form of Next, as an electron injection and transport layer, a compound represented by the following chemical formula ET1 and a compound represented by the following Liq were added at a weight ratio of 1:1 and at a weight ratio of On the electron injection and transport layer, lithium fluoride (LiF) is deposited in the form of The thickness of the aluminum A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0428]

[0429] Experimental Examples 1-2 to 1-34 and Comparative Examples 1-1 to 1-5.

[0430] An organic light-emitting device was produced by the same method as in Experimental Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1.

[0431] Compounds EB1 to EB5 used in Comparative Examples are shown below.

[0432]

[0433] The organic light-emitting devices manufactured in the experimental examples and comparative examples were subjected to a 10 mA / cm 2 The voltage, efficiency, color coordinates and life were measured when the current was 1.5 % and 2.5 % respectively. The results are shown in Table 1. T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

[0434]

Table 1

[0435]

[0436]

[0437]

[0438] As shown in Table 1, it was confirmed that the compound of the present invention has excellent electron blocking ability, and an organic light-emitting device using the compound as an electron blocking layer exhibits effects of reduced driving voltage, excellent efficiency and lifetime.

[0439] On the contrary, when it can be confirmed that Ar3 in Chemical Formula 1 is a monocyclic aromatic group (Comparison Example 1-1), or L1 is substituted by a substituent other than deuterium (Comparison Example 1-2), or phenanthrene 2 or 9 is not substituted (Comparison Examples 1-3, 1-4), or phenanthrene also contains a substituent at other positions (Comparison Example 1-5), the driving voltage is increased and the efficiency and life are reduced compared with the examples.

[0440] Experimental Examples 2-1 to 2-34 and Comparative Examples 2-1 to 2-5

[0441] In the above-mentioned experimental example 1-1, the compound represented by the above-mentioned chemical formula EB1 is used instead of compound 1 as the electron blocking layer, and the compound described in the following Table 2 is used instead of the compound represented by the above-mentioned chemical formula HT1 as the hole transport layer. Except for this, an organic light-emitting device is prepared by the same method as the above-mentioned experimental example 1-1.

[0442] Compounds HT2 to HT6 used in Comparative Examples are shown below.

[0443]

[0444] The organic light-emitting devices manufactured in the experimental examples and comparative examples were subjected to a 10 mA / cm 2 The voltage, efficiency, color coordinates and life were measured when the current was 1.5 %. The results are shown in Table 2. T95 refers to the time required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0445]

Table 2

[0446]

[0447]

[0448]

[0449] As shown in Table 2, it was confirmed that the compound of the present invention has excellent hole transporting ability, and an organic light-emitting device using the compound as a hole transporting layer exhibits effects of reduced driving voltage, excellent efficiency and life.

[0450] On the contrary, when it can be confirmed that the compound of Chemical Formula 1 is not contained (Comparison Example 1-1), or Ar3 in Chemical Formula 1 is a monocyclic aromatic group (Comparison Example 2-1), or No. 2 or No. 9 of phenanthrene is not substituted (Comparison Examples 2-2, 2-3), or L1 is substituted by other substituents other than deuterium (Comparison Example 2-4), or other positions of phenanthrene also contain substituents (Comparison Example 2-5), compared with the embodiments, the driving voltage is increased, and the efficiency and life are reduced.

Claims

1. A compound of the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, R1 to R3 are the same as or different from each other, and are each independently hydrogen or deuterium, L1 and L4 are the same as or different from each other, and are each independently a direct bond, an arylene group substituted or unsubstituted by deuterium, or a heteroarylene group substituted or unsubstituted by deuterium, L2 and L3 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, Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, or a substituted or unsubstituted heteroaryl group, Ar3 is a substituted or unsubstituted polycyclic aryl group, or a substituted or unsubstituted heteroaryl group, l2 and l3 are each an integer from 1 to 3. When l2 is 2 or more, two or more L2s are the same or different from each other. When l3 is 2 or more, two or more L3s are the same or different from each other. r2 is an integer from 1 to 4. When r2 is 2 or more, two or more R2s are the same or different from each other. r3 is an integer from 1 to 3. When r3 is 2 or more, two or more R3s are the same or different from each other.

2. The compound according to claim 1, wherein Ar3 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted triphenylene group.

3. The compound according to claim 1, wherein The L1 is a direct bond, a phenylene group substituted or unsubstituted by deuterium, a biphenylene group substituted or unsubstituted by deuterium, or a naphthylene group substituted or unsubstituted by deuterium.

4. The compound according to claim 1, wherein The L2 and L3 are the same as or different from each other and are independently directly bonded; substituted or unsubstituted arylene groups selected from deuterium, alkyl groups and aryl groups; or substituted or unsubstituted heteroarylene groups selected from deuterium, alkyl groups and aryl groups.

5. The compound according to claim 1, wherein The L2 and L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted divalent fluorenyl group, a substituted or unsubstituted divalent spirobifluorenyl group, or a substituted or unsubstituted divalent phenanthryl group.

6. The compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other and are independently hydrogen; deuterium; an alkyl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; an aryl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; a fused ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group; or a heteroaryl group substituted or unsubstituted by one or more selected from deuterium, an alkyl group and an aryl group.

7. The compound according to claim 1, wherein The Ar1 and Ar2 are the same or different from each other, and are independently any one of the following structures: In the structure described, R10 to R16 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, The structure is substituted or unsubstituted with one or more substituents selected from deuterium, alkyl and aryl, ------ is a part combined with chemical formula 1.

8. The compound according to claim 1, wherein The compound is selected from the following structures: In the structure, Dn is the number of deuterium contained in the compound.

9. An organic light-emitting device, comprising: a first electrode; a second electrode; as well as one or more organic layers, the organic layers including a light-emitting layer disposed between the first electrode and the second electrode, One or more of the organic layers contains the compound according to any one of claims 1 to 8.

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

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

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