Compounds and organic light emitting devices comprising the same

Abstract

The present application relates to a compound represented by Chemical Formula 1 and an organic light emitting device comprising the same.

Description

Technical Field

[0001] This invention claims priority to Korean Patent Application No. 10-2020-0134252, filed with the Korean Patent Office on October 16, 2020, the entire contents of which are incorporated herein by reference.

[0002] This invention relates to compounds and organic light-emitting devices containing the same. Background Technology

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure including an anode and a cathode, and an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When this exciton re-enters the ground state, it emits light.

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

[0005] (Patent Document 1) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0006] Technical issues

[0007] This invention provides compounds and / or organic light-emitting devices containing them.

[0008] Solution to the problem

[0009] One embodiment of the present invention provides a compound represented by the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X is O or S.

[0014] Ar is an alkyl group with 10 to 30 carbon atoms, aryl group with 10 to 30 carbon atoms, or heterocyclic group with 10 to 30 carbon atoms, whether substituted or unsubstituted.

[0015] L represents a directly bonded, substituted, or unsubstituted aryl group.

[0016] R1 to R5 may be the same as or different from each other, and each is independently a hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or may combine with adjacent groups to form substituted or unsubstituted rings.

[0017] r1 to r5 are each an integer from 0 to 4.

[0018] When r1 to r5 are 2 or more, the substituents in parentheses may be the same or different from each other.

[0019] In addition, another embodiment of the present invention provides an organic light-emitting device, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound represented by the above chemical formula 1.

[0020] Invention Effects

[0021] The compound according to one embodiment of the present invention can be used as a material for the organic layer of an organic light-emitting device.

[0022] The compound according to one embodiment of the present invention can be used as an electron blocking layer material for organic light-emitting devices.

[0023] The compound according to one embodiment of the present invention is included in an organic light-emitting device, thereby improving the device characteristics, for example, giving the device a low driving voltage, excellent efficiency characteristics, or excellent lifetime characteristics. Attached Figure Description

[0024] Figure 1 An organic light-emitting device according to an embodiment of the present invention is illustrated.

[0025] Figure 2 An organic light-emitting device according to another embodiment of the present invention is illustrated.

[0026] [Symbol Explanation]

[0027] 1: Substrate

[0028] 2: Anode

[0029] 3: Organic layer

[0030] 4: Hole injection layer

[0031] 5: Hole transport layer

[0032] 6: Emissive layer

[0033] 7: Cavity barrier layer

[0034] 8: Electron Injection and Transport Layer

[0035] 10: Cathode

[0036] 100: Electron blocking layer Detailed Implementation

[0037] The present invention will now be described in more detail.

[0038] One embodiment of the present invention provides a compound represented by the following chemical formula 1.

[0039] [Chemical Formula 1]

[0040]

[0041] In the above chemical formula 1,

[0042] X is O or S.

[0043] Ar is an alkyl group with 10 to 30 carbon atoms, aryl group with 10 to 30 carbon atoms, or heterocyclic group with 10 to 30 carbon atoms, whether substituted or unsubstituted.

[0044] L represents a directly bonded, substituted, or unsubstituted aryl group.

[0045] R1 to R5 may be the same as or different from each other, and each is independently a hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or may combine with adjacent groups to form substituted or unsubstituted rings.

[0046] r1 to r5 are each an integer from 0 to 4.

[0047] When r1 to r5 are 2 or more, the substituents in parentheses may be the same or different from each other.

[0048] One embodiment of the present invention provides a compound represented by the above chemical formula 1.

[0049] In the present invention, chemical formula 1 has an amino group bonded to the para position of the biphenyl group and a carbazole group bonded to the ortho position via direct bonding or a linking group (L). This allows for a higher maintenance of the HOMO (highest occupied molecular orbital) value, reducing the energy barrier with adjacent light-emitting layers and thus appropriately maintaining charge balance. Furthermore, when an organic layer containing a compound represented by chemical formula 1 is used as an electron blocking layer, the generated excitons are confined within the light-emitting layer to prevent light leakage, thereby achieving an organic light-emitting device with excellent luminous efficiency. As a result, when a compound of chemical formula 1 is used as an electron blocking layer, the long lifetime, low voltage, or high efficiency characteristics of the organic light-emitting device are enhanced.

[0050] In this invention, examples of substituents are described below, but are not limited thereto.

[0051] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0052] In this invention, the term "substituted or unsubstituted" refers to being substituted by one or more substituents selected from deuterium, halogen groups, nitrile groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups, or being substituted by a substituent formed by linking two or more substituents among the substituents exemplified above, or having no substituents. For example, "a substituent formed by linking two or more substituents" can be an aryl group substituted with an aryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, etc.

[0053] In this invention, "a ring formed by the combination of adjacent groups" refers to a hydrocarbon ring or a heterocycle.

[0054] In this invention, the halogen group can be F, Cl, Br, I, etc.

[0055] In this invention, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferably 1 to 10 carbon atoms. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, and tert-butyl. (hereinafter referred to as tert-butyl) sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but not limited to these.

[0056] In this invention, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 30 carbon atoms, and more preferably a cycloalkyl group with 3 to 20 carbon atoms. Specifically, it includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but is not limited to these.

[0057] In this invention, the silyl group can be represented by the chemical formula -SiRaRbRc, where Ra, Rb, and Rc may be the same or different from each other, and each can independently be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited to these.

[0058] In this invention, the amino group can be represented by -NRdRe, where Rd and Re may be the same or different from each other, and each can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, but is not limited thereto. The amino group can be selected from alkylamino, alkylarylamino, arylamino, heteroarylamino, alkylheteroarylamino, and arylheteroarylamino, depending on the type of substituent (Rd, Re) it is bonded to.

[0059] In this invention, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 30 carbon atoms, more preferably an aryl group with 6 to 20 carbon atoms. The aryl group can be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. More specifically, the number of carbon atoms is preferably 6 to 20. Specifically, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30, more specifically, the number of carbon atoms is preferably 10 to 20. Specifically, as a polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthrene, triphenylene, pyrene, beryl, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0060] In this invention, the substituted aryl group may also include a configuration in which an aliphatic ring is fused to the aryl group. For example, the tetrahydronaphthyl group in the following structure contains the substituted aryl group. In the following structure, one of the carbon atoms of the benzene ring may be attached to other positions.

[0061]

[0062] In this invention, the heterocyclic group is a cyclic group containing one or more of N, O, S, and Si as heteroatoms. The number of carbon atoms is not particularly limited, but is 2 to 60 or 2 to 30. Examples of the aforementioned heterocyclic groups include pyridyl, quinolinyl, thiophenyl, dibenzothiophenyl, furanyl, dibenzofuranyl, naphthobenzofuranyl, carbazoleyl, benzocarbazoleyl, naphthobenzothiophenyl, hexahydrocarbazoleyl, dihydroacridyl, dihydrodibenzosilazylhexyl, and phenyl... Phenoxazine, phenothiazine, spiro(dibenzothiophene-dibenzosilazane), spiro(acridin-fluorene), etc., but not limited to these.

[0063] In this invention, the hydrocarbon ring can be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds. The aromatic hydrocarbon ring, except that it is not monovalent, is subject to the above description regarding aryl groups. The aliphatic hydrocarbon ring, except that it is not monovalent, is subject to the above description regarding cycloalkyl groups. Examples of fused rings of aromatic and aliphatic compounds include 1,2,3,4-tetrahydronaphthyl and 2,3-dihydro-1H-indenyl, but the invention is not limited to these.

[0064] In this invention, an aromatic hydrocarbon ring refers to a planar ring with fully conjugated π electrons, and the above description of aryl groups applies except that the ring is a divalent group.

[0065] In this invention, aliphatic hydrocarbon rings refer to all hydrocarbon rings other than aromatic hydrocarbon rings, and may include cycloalkyl rings. The above description of cycloalkyl rings applies, except that they are divalent groups. Substituted aliphatic hydrocarbon rings also include aliphatic hydrocarbon rings fused with aromatic rings.

[0066] In this invention, the arylene group, except that it is a divalent group, can be described in the above description of the aryl group.

[0067] In this invention, the heteroaryl group comprises one or more non-carbon atoms, i.e., heteroatoms. Specifically, the heteroatoms may comprise one or more atoms selected from O, N, Se, and S. The number of carbon atoms is not particularly limited, but preferably 2 to 30, more preferably 2 to 20. The heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso The group can be azole, thiadiazole, phenothiazinyl, or dibenzofuranyl, but is not limited to these.

[0068] In this invention, heteroaryl groups, in addition to being aromatic, can be described in the above description of heterocyclic groups.

[0069] In this invention, "adjacent" groups can refer to substituents that are substituted on an atom directly connected to the atom substituted by the substituent, substituents that are stereoscopically closest to the substituent, or other substituents that are substituted on the atom substituted by the substituent. For example, two substituents in a benzene ring that are substituted at the ortho position and two substituents on the same carbon atom in an aliphatic ring can be interpreted as "adjacent" groups.

[0070] According to one embodiment of the present invention, the above chemical formula 1 is represented by any one of the following chemical formulas 2 to 5.

[0071] [Chemical Formula 2]

[0072]

[0073] [Chemical Formula 3]

[0074]

[0075] [Chemical Formula 4]

[0076]

[0077] [Chemical Formula 5]

[0078]

[0079] In the above chemical formulas 2 to 5, X, Ar, L, R1 to R5, and r1 to r5 are defined in the same way as in the above chemical formula 1.

[0080] According to one embodiment of the present invention, R1 and R2 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or combined with adjacent groups to form substituted or unsubstituted rings.

[0081] According to one embodiment of the present invention, R1 and R2 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, or aryl with 6 to 30 carbon atoms, or combined with adjacent groups to form a substituted or unsubstituted ring with 2 to 30 carbon atoms.

[0082] According to one embodiment of the present invention, R1 and R2 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a ring with 2 to 30 substituted or unsubstituted carbon atoms formed by combining with adjacent groups.

[0083] According to one embodiment of the present invention, R1 and R2 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, or an aryl group having 6 to 30 carbon atoms, or is combined with adjacent groups to form a ring having 2 to 30 carbon atoms.

[0084] According to one embodiment of the present invention, R1 and R2 of the above-mentioned chemical formula 1 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraceneyl, or substituted or unsubstituted phenanthryl, or combined with adjacent groups to form a substituted or unsubstituted benzene ring.

[0085] According to one embodiment of the present invention, R1 and R2 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, phenyl, naphthyl, anthraceneyl or phenanthrene, or may be combined with adjacent groups to form a benzene ring.

[0086] According to one embodiment of the present invention, R1 and R2 of the above-mentioned chemical formula 1 are the same or different from each other, and are each independently hydrogen, deuterium, or substituted or unsubstituted phenyl, or are combined with adjacent groups to form substituted or unsubstituted benzene rings.

[0087] According to one embodiment of the present invention, R1 and R2 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium or phenyl, or may be combined with adjacent groups to form a benzene ring.

[0088] According to one embodiment of the present invention, R1 of the above-mentioned chemical formula 1 combines with adjacent groups to form a benzene ring.

[0089] According to one embodiment of the present invention, R2 of the above-mentioned chemical formula 1 combines with adjacent groups to form a benzene ring.

[0090] According to one embodiment of the present invention, R3 and R4 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or combined with adjacent groups to form substituted or unsubstituted rings.

[0091] According to one embodiment of the present invention, R3 and R4 of the above-mentioned chemical formula 1 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, or aryl with 6 to 30 carbon atoms, or combined with adjacent groups to form a substituted or unsubstituted ring with 2 to 30 carbon atoms.

[0092] According to one embodiment of the present invention, R3 and R4 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a ring with 2 to 30 substituted or unsubstituted carbon atoms formed by combining with adjacent groups.

[0093] According to one embodiment of the present invention, R3 and R4 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, or an aryl group having 6 to 30 carbon atoms, or is combined with adjacent groups to form a ring having 2 to 30 carbon atoms.

[0094] According to one embodiment of the present invention, R3 and R4 of the above-mentioned chemical formula 1 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, or substituted or unsubstituted phenanthryl, or combined with adjacent groups to form a substituted or unsubstituted benzene ring.

[0095] According to one embodiment of the present invention, R3 and R4 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, phenyl, naphthyl, anthraceneyl or phenanthrene, or may be combined with adjacent groups to form a benzene ring.

[0096] According to one embodiment of the present invention, R3 and R4 of the above chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group, or combined with adjacent groups to form a substituted or unsubstituted benzene ring.

[0097] According to one embodiment of the present invention, R3 and R4 of the above-mentioned chemical formula 1 may be the same or different from each other, and each is independently hydrogen, deuterium or phenyl, or may be combined with adjacent groups to form a benzene ring.

[0098] According to one embodiment of the present invention, R3 of the above-mentioned chemical formula 1 combines with adjacent groups to form a benzene ring.

[0099] According to one embodiment of the present invention, R4 of the above-mentioned chemical formula 1 combines with adjacent groups to form a benzene ring.

[0100] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 is hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or a substituted or unsubstituted ring formed by combining with adjacent groups.

[0101] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 is hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a ring having substituted or unsubstituted carbon atoms formed by combining with adjacent groups.

[0102] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 is hydrogen, deuterium, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a ring with 2 to 30 substituted or unsubstituted carbon atoms formed by combining with adjacent groups.

[0103] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 is hydrogen, deuterium, or an aryl group having 6 to 30 carbon atoms, or a ring having 2 to 30 carbon atoms formed by combining with adjacent groups.

[0104] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, or substituted or unsubstituted phenanthryl, or a substituted or unsubstituted benzene ring formed by combining with adjacent groups.

[0105] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 is hydrogen, deuterium, phenyl, naphthyl, anthraceneyl or phenanthrene, or it may combine with adjacent groups to form a benzene ring.

[0106] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 is hydrogen, deuterium, or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzene ring formed by combining with adjacent groups.

[0107] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 is hydrogen, deuterium or phenyl, or it may combine with adjacent groups to form a benzene ring.

[0108] According to one embodiment of the present invention, R5 of the above-mentioned chemical formula 1 combines with adjacent groups to form a benzene ring.

[0109] According to one embodiment of the present invention, r1 to r5 are each an integer from 0 to 4.

[0110] According to one embodiment of the present invention, r1 is an integer 0. According to another embodiment of the present invention, r1 is an integer 1. According to another embodiment of the present invention, r1 is an integer 2. According to another embodiment of the present invention, r1 is an integer 3. According to another embodiment of the present invention, r1 is an integer 4. When r1 is 2 or more, the R1s within the parentheses are the same or different from each other.

[0111] According to one embodiment of the present invention, r2 is an integer 0. According to another embodiment of the present invention, r2 is an integer 1. According to another embodiment of the present invention, r2 is an integer 2. According to another embodiment of the present invention, r2 is an integer 3. According to another embodiment of the present invention, r2 is an integer 4. When r2 is 2 or more, the R2s within the parentheses are the same or different from each other.

[0112] According to one embodiment of the present invention, r3 is an integer 0. According to another embodiment of the present invention, r3 is an integer 1. According to another embodiment of the present invention, r3 is an integer 2. According to another embodiment of the present invention, r3 is an integer 3. According to another embodiment of the present invention, r3 is an integer 4. When r3 is 2 or more, the R3s within the parentheses are the same or different from each other.

[0113] According to one embodiment of the present invention, r4 is an integer 0. According to another embodiment of the present invention, r4 is an integer 1. According to another embodiment of the present invention, r4 is an integer 2. According to another embodiment of the present invention, r4 is an integer 3. According to another embodiment of the present invention, r4 is an integer 4. When r4 is 2 or more, the R4s within the parentheses are the same or different from each other.

[0114] According to one embodiment of the present invention, r5 is an integer 0. According to another embodiment of the present invention, r5 is an integer 1. According to another embodiment of the present invention, r5 is an integer 2. According to another embodiment of the present invention, r5 is an integer 3. According to another embodiment of the present invention, r5 is an integer 4. When r5 is 2 or more, the R5s within the parentheses are the same or different from each other.

[0115] According to one embodiment of the present invention, L in the above chemical formula 1 is a directly bonded, substituted, or unsubstituted aryl group.

[0116] According to one embodiment of the present invention, L in the above-described chemical formula 1 is an arylene group having 6 to 30 carbon atoms, either directly bonded, substituted, or unsubstituted. According to another embodiment of the present invention, L in the above-described chemical formula 1 is an arylene group having 6 to 20 carbon atoms, either directly bonded, substituted, or unsubstituted. According to yet another embodiment of the present invention, L in the above-described chemical formula 1 is an arylene group having 6 to 12 carbon atoms, either directly bonded, substituted, or unsubstituted.

[0117] According to one embodiment of the present invention, L in the above-mentioned chemical formula 1 is a directly bonded aryl group, or an aryl group having 6 to 30 carbon atoms. According to another embodiment of the present invention, L in the above-mentioned chemical formula 1 is a directly bonded aryl group, or an aryl group having 6 to 20 carbon atoms. According to yet another embodiment of the present invention, L in the above-mentioned chemical formula 1 is a directly bonded aryl group, or an aryl group having 6 to 12 carbon atoms.

[0118] According to one embodiment of the present invention, L in the above-mentioned chemical formula 1 is a directly bonded, substituted or unsubstituted phenylene, a substituted or unsubstituted divalent biphenyl, a substituted or unsubstituted divalent triphenyl, a substituted or unsubstituted naphthylene, a substituted or unsubstituted anthraceneylene, or a substituted or unsubstituted phenanthrylene.

[0119] According to one embodiment of the present invention, L in the above-mentioned chemical formula 1 is a directly bonded, substituted or unsubstituted phenylene, a substituted or unsubstituted divalent biphenyl, or a substituted or unsubstituted naphthylene.

[0120] According to one embodiment of the present invention, L in the above chemical formula 1 is directly bonded, phenylene, divalent biphenyl, or naphthylene.

[0121] According to one embodiment of the present invention, L in the above chemical formula 1 is a directly bonded, substituted, or unsubstituted phenylene.

[0122] According to one embodiment of the present invention, L in the above chemical formula 1 is a direct bond or a phenylene oxide.

[0123] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is a substituted or unsubstituted alkyl group with 10 to 30 carbon atoms, a substituted or unsubstituted aryl group with 10 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group with 10 to 30 carbon atoms.

[0124] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is an alkyl group with 10 to 20 substituted or unsubstituted carbon atoms, an aryl group with 10 to 20 substituted or unsubstituted carbon atoms, or a heterocyclic group with 10 to 20 substituted or unsubstituted carbon atoms.

[0125] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is an aryl group with 10 to 30 substituted or unsubstituted carbon atoms, or a heterocyclic group with 10 to 30 substituted or unsubstituted carbon atoms.

[0126] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is an aryl group with 10 to 25 substituted or unsubstituted carbon atoms, or a heterocyclic group with 10 to 25 substituted or unsubstituted carbon atoms.

[0127] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is an aryl group with 10 to 20 substituted or unsubstituted carbon atoms, or a heterocyclic group with 10 to 20 substituted or unsubstituted carbon atoms.

[0128] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is an aryl group with 10 to 30 carbon atoms or a heterocyclic group with 10 to 30 carbon atoms.

[0129] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is an aryl group with 10 to 25 carbon atoms or a heterocyclic group with 10 to 25 carbon atoms.

[0130] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is an aryl group with 10 to 20 carbon atoms or a heterocyclic group with 10 to 20 carbon atoms.

[0131] According to one embodiment of the present invention, Ar of the above-mentioned chemical formula 1 is a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0132] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, dibenzofuranyl or dibenzothiophene.

[0133] According to one embodiment of the present invention, Ar of the above-mentioned chemical formula 1 is a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a naphthyl substituted or unsubstituted with phenyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0134] According to one embodiment of the present invention, Ar in the above-mentioned chemical formula 1 is biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, dibenzofuranyl, or dibenzothiophene.

[0135] According to one embodiment of the present invention, Ar in the above chemical formula 1 is selected from any one of the following groups 1.

[0136] [Group 1]

[0137]

[0138] The structure selected from group 1 above is substituted or unsubstituted by one or more substituents selected from deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic groups.

[0139] In the above structure, the dashed line indicates the position where it bonds with N in chemical formula 1.

[0140] According to one embodiment of the present invention, the above chemical formula 1 is represented by any one of the following chemical formulas 61 to 63.

[0141] [Chemical Formula 61]

[0142]

[0143] [Chemical Formula 62]

[0144]

[0145] [Chemical Formula 63]

[0146]

[0147] In the above chemical formulas 61 to 63,

[0148] R61 to R63 may be the same as or different from each other, and each is independently a hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group, or substituted or unsubstituted aryl group.

[0149] r61 to r63 are each an integer from 0 to 6.

[0150] When r61 to r63 are 2 or more, the substituents within the parentheses may be the same or different from each other.

[0151] X, Ar, L, R1 to R4, and r1 to r4 are the same as those defined in Chemical Formula 1 above.

[0152] According to one embodiment of the present invention, R61 to R63 may be the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms. According to another embodiment of the present invention, R61 to R63 may be the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group with 1 to 10 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0153] According to one embodiment of the present invention, R61 to R63 may be the same as or different from each other, and each is independently hydrogen, deuterium, or an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0154] According to one embodiment of the present invention, R61 to R63 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0155] According to one embodiment of the present invention, R61 to R63 may be the same as or different from each other, and each is independently hydrogen, deuterium, phenyl, biphenyl or naphthyl.

[0156] According to one embodiment of the present invention, R61 to R63 may be the same as or different from each other, and each is independently hydrogen, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl.

[0157] According to one embodiment of the present invention, R61 to R63 may be the same as or different from each other, and each is independently hydrogen, phenyl or naphthyl.

[0158] According to one embodiment of the present invention, R61 to R63 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0159] According to one embodiment of the present invention, each of R61 to R63 is hydrogen.

[0160] According to one embodiment of the present invention, r61 is an integer 0. According to another embodiment of the present invention, r61 is an integer 1. According to another embodiment of the present invention, r61 is an integer 2. According to another embodiment of the present invention, r61 is an integer 3. According to another embodiment of the present invention, r61 is an integer 4. According to another embodiment of the present invention, r61 is an integer 5. According to another embodiment of the present invention, r61 is an integer 6. When r61 is 2 or more, the r61s within the parentheses are the same or different from each other.

[0161] According to one embodiment of the present invention, r62 is an integer 0. According to another embodiment of the present invention, r62 is an integer 1. According to another embodiment of the present invention, r62 is an integer 2. According to another embodiment of the present invention, r62 is an integer 3. According to another embodiment of the present invention, r62 is an integer 4. According to another embodiment of the present invention, r62 is an integer 5. According to another embodiment of the present invention, r62 is an integer 6. When r62 is 2 or more, the r62s within the parentheses are the same or different from each other.

[0162] According to one embodiment of the present invention, r63 is an integer 0. According to another embodiment of the present invention, r63 is an integer 1. According to another embodiment of the present invention, r63 is an integer 2. According to another embodiment of the present invention, r63 is an integer 3. According to another embodiment of the present invention, r63 is an integer 4. According to another embodiment of the present invention, r63 is an integer 5. According to another embodiment of the present invention, r63 is an integer 6. When r63 is 2 or more, the r63s within the parentheses are the same or different from each other.

[0163] According to one embodiment of the present invention, the above chemical formula 1 is represented by any one of the following chemical formulas 71 to 73.

[0164] [Chemical Formula 71]

[0165]

[0166] [Chemical Formula 72]

[0167]

[0168] [Chemical Formula 73]

[0169]

[0170] In the above chemical formulas 71 to 73,

[0171] R11 to R13 may be the same as or different from each other, and each is independently hydrogen, deuterium, halogen group, cyano, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0172] r11 to r13 are each an integer from 0 to 6.

[0173] When r11 to r13 are 2 or more, the substituents within the parentheses may be the same or different from each other.

[0174] X, Ar, L, R2 to R5, and r2 to r5 are the same as those defined in the above chemical formula 1.

[0175] According to one embodiment of the present invention, R11 to R13 may be the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, an alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 30 substituted or unsubstituted carbon atoms. According to another embodiment of the present invention, R11 to R13 are hydrogen, deuterium, a halogen group, a cyano group, an alkyl group with 1 to 10 substituted or unsubstituted carbon atoms, or an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0176] According to one embodiment of the present invention, R11 to R13 may be the same as or different from each other, and each is independently hydrogen, deuterium, or an aryl group with 6 to 20 substituted or unsubstituted carbon atoms.

[0177] According to one embodiment of the present invention, R11 to R13 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0178] According to one embodiment of the present invention, R11 to R13 may be the same as or different from each other, and each is independently hydrogen, deuterium, phenyl, biphenyl or naphthyl.

[0179] According to one embodiment of the present invention, R11 to R13 may be the same as or different from each other, and each is independently hydrogen, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl.

[0180] According to one embodiment of the present invention, R11 to R13 may be the same as or different from each other, and each is independently hydrogen, phenyl or naphthyl.

[0181] According to one embodiment of the present invention, R11 to R13 may be the same as or different from each other, and each is independently hydrogen or deuterium.

[0182] According to one embodiment of the present invention, each of R11 to R13 is hydrogen.

[0183] According to one embodiment of the present invention, r11 is an integer 0. According to another embodiment of the present invention, r11 is an integer 1. According to another embodiment of the present invention, r11 is an integer 2. According to another embodiment of the present invention, r11 is an integer 3. According to another embodiment of the present invention, r11 is an integer 4. According to another embodiment of the present invention, r11 is an integer 5. According to another embodiment of the present invention, r11 is an integer 6. When r11 is 2 or more, the R11s within the parentheses are the same or different from each other.

[0184] According to one embodiment of the present invention, r12 is an integer 0. According to another embodiment of the present invention, r12 is an integer 1. According to another embodiment of the present invention, r12 is an integer 2. According to another embodiment of the present invention, r12 is an integer 3. According to another embodiment of the present invention, r12 is an integer 4. According to another embodiment of the present invention, r12 is an integer 5. According to another embodiment of the present invention, r12 is an integer 6. When r12 is 2 or more, the R12s within the parentheses are the same or different from each other.

[0185] According to one embodiment of the present invention, r13 is an integer 0. According to another embodiment of the present invention, r13 is an integer 1. According to another embodiment of the present invention, r13 is an integer 2. According to another embodiment of the present invention, r13 is an integer 3. According to another embodiment of the present invention, r13 is an integer 4. According to another embodiment of the present invention, r13 is an integer 5. According to another embodiment of the present invention, r13 is an integer 6. When r13 is 2 or more, the R13s within the parentheses are the same or different from each other.

[0186] According to one embodiment of the present invention, the above-mentioned chemical formula 1 is selected from any of the following compounds.

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196] The compound represented by chemical formula 1 according to an embodiment of the present invention can be synthesized by methods known in the art or by the synthetic examples described later. The type, position, or number of substituents can be varied according to techniques known in the art. Specific synthetic examples will be described later.

[0197] One embodiment of the present invention provides an organic light-emitting device, comprising: an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a compound represented by the above-described chemical formula 1. As an example, the organic layer comprising the compound represented by the above-described chemical formula 1 is a light-emitting layer.

[0198] According to another embodiment of the present invention, the above-described organic light-emitting device includes two or more organic layers, wherein the two or more organic layers contain a compound represented by the above-described chemical formula 1. For example, any one of the two or more organic layers contains a compound represented by the above-described chemical formula 1, and the device also includes one or more other organic layers. According to one embodiment, the other one or more organic layers do not contain a compound represented by the above-described chemical formula 1. According to another embodiment, the other one or more organic layers further contain a compound represented by the above-described chemical formula 1. However, the device is not limited to the above examples. For example, the two or more organic layers include two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. In this case, a hole injection and transport layer refers to a layer in which hole injection and hole transport are performed simultaneously, and an electron injection and transport layer refers to a layer in which electron injection and electron transport are performed simultaneously. However, the organic layers constituting the above group are merely examples and are not limited to these examples. As a specific example, the organic light-emitting device includes two or more organic layers, with any one organic layer serving as a light-emitting layer, and the remaining one or more organic layers containing a compound represented by the above-described chemical formula 1. As a more specific example, the organic light-emitting device includes two or more organic layers, with any one organic layer serving as a light-emitting layer, and the remaining organic layers containing an electron-blocking layer containing a compound represented by the above-described chemical formula 1.

[0199] Furthermore, the aforementioned two or more organic layers may include two or more layers performing the same function, as needed. An illustrated organic light-emitting device includes a first electron-blocking layer and a second electron-blocking layer. However, it is not limited to the above example. When the aforementioned organic light-emitting device includes a plurality of organic layers, the organic layers may be formed from the same material or different materials.

[0200] According to one embodiment of the present invention, the organic layer includes a light-emitting layer. As an example, the light-emitting layer comprises a compound represented by Chemical Formula 1. As a specific example, the light-emitting layer comprises a compound represented by Chemical Formula 1 as the main body of the light-emitting layer. As another specific example, the light-emitting layer comprises a compound represented by Chemical Formula 1 as a dopant of the light-emitting layer.

[0201] According to one embodiment of the present invention, the organic layer further includes one or more layers selected from the electron blocking layer, hole blocking layer, hole injection layer, hole transport layer, and hole injection and transport layer. As an example, one or more layers selected from the electron blocking layer, hole blocking layer, hole injection layer, hole transport layer, and hole injection and transport layer comprise a compound represented by the above chemical formula 1.

[0202] The following is a detailed description of the above-mentioned organic layer and the stacked structure of the organic light-emitting device including it.

[0203] According to one embodiment of the organic light-emitting device of the present invention, the organic layer is a single-layer structure. For example, the organic layer of the above-mentioned single-layer structure is disposed between the anode and cathode of the organic light-emitting device, and the organic layer contains a compound represented by the above-mentioned chemical formula 1. According to a specific embodiment, the organic layer composed of the above-mentioned single-layer structure is a light-emitting layer, in which case the light-emitting layer contains a compound represented by the above-mentioned chemical formula 1.

[0204] According to another embodiment of the present invention, the organic layer of the organic light-emitting device is a multilayer structure having two or more organic layers stacked on top of each other. For example, the organic layer of the multilayer structure is disposed between the anode and the cathode of the organic light-emitting device.

[0205] According to one embodiment of the present invention, the organic layer of the multilayer structure includes a light-emitting layer and organic layers other than the light-emitting layer. As an example, the light-emitting layer is disposed between the anode and the cathode, and the organic layers other than the light-emitting layer are disposed between the anode and the light-emitting layer. As another example, the light-emitting layer is disposed between the anode and the cathode, and the organic layers other than the light-emitting layer are disposed between the light-emitting layer and the cathode. As yet another example, the light-emitting layer is disposed between the anode and the cathode, any organic layer other than the light-emitting layer is disposed between the anode and the light-emitting layer, and any other organic layer other than the light-emitting layer is disposed between the light-emitting layer and the cathode. However, the above structures are merely illustrative and are not limited to these structures. Furthermore, the organic layers other than the light-emitting layer may be, for example, one or more layers selected from hole injection and transport layers, hole injection layers, hole transport layers, electron blocking layers, hole blocking layers, electron transport layers, electron injection layers, electron injection and transport layers, etc., but are not limited thereto.

[0206] Typically, in organic light-emitting devices, a hole injection layer, a hole transport layer, or an electron blocking layer is disposed between the anode and the light-emitting layer. As a specific example, the hole injection layer is disposed above the anode, the hole transport layer is disposed above the hole injection layer, and the electron blocking layer is disposed above the hole injection layer, but the method is not limited to the examples described above.

[0207] Furthermore, in organic light-emitting devices, an electron injection layer, an electron transport layer, or a hole blocking layer is typically disposed between the cathode and the light-emitting layer. As a specific example, the hole blocking layer is disposed above the light-emitting layer, the electron transport layer is disposed above the hole blocking layer, and the electron injection layer is disposed above the electron transport layer, but this is not limited to the examples described above.

[0208] An organic light-emitting device according to an embodiment of the present invention includes an organic layer with a multilayer structure, comprising a light-emitting layer; and one or more organic layers selected from hole injection and transport layers, hole injection layers, hole transport layers, electron blocking layers, hole blocking layers, electron transport layers, electron injection layers, and electron injection and transport layers, wherein the light-emitting layer is disposed between an anode and a cathode.

[0209] According to a preferred embodiment of the present invention, the aforementioned one or more organic layers are at least one of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer. More preferably, the aforementioned one or more organic layers are an electron blocking layer.

[0210] According to one embodiment of the present invention, the organic layer includes an electron blocking layer, which contains a compound represented by the above chemical formula 1.

[0211] According to one embodiment of the present invention, the organic layer includes a hole injection layer.

[0212] According to one embodiment of the present invention, the above-mentioned organic layer includes a hole transport layer.

[0213] According to one embodiment of the present invention, the above-mentioned organic layer includes a hole injection and transport layer.

[0214] According to one embodiment of the present invention, the above-mentioned organic layer includes one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer.

[0215] According to one embodiment of the present invention, the organic layer includes a light-emitting layer; and one or more layers selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer, wherein the layers selected from the hole injection layer, the hole transport layer, the hole injection and transport layer, and the electron blocking layer contain the aforementioned compound.

[0216] According to one embodiment of the present invention, the above-mentioned organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the hole injection layer, hole transport layer, or hole injection and transport layer may contain the above-mentioned compound.

[0217] One embodiment of the present invention provides an organic light-emitting device, comprising: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein the one or more organic layers comprise a compound represented by chemical formula 1. Another embodiment of the present invention provides an organic light-emitting device, comprising: an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, wherein the two or more organic layers include a light-emitting layer; and at least one layer selected from a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer, wherein at least one of the hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer comprises a compound represented by chemical formula 1. A specific embodiment of the present invention provides an organic light-emitting device, comprising: an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, wherein the two or more organic layers include a light-emitting layer; and an electron blocking layer comprising a compound represented by chemical formula 1.

[0218] For example, the organic light-emitting device described above can have a stacked structure as shown below, but is not limited to this.

[0219] (1) Anode / hole transport layer / light-emitting layer / cathode

[0220] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0221] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0222] (4) Anode / Hole transport layer / Light emission layer / Electron transport layer / Cathode

[0223] (5) Anode / Hole transport layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0224] (6) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0225] (7) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0226] (8) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0227] (9) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0228] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0229] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0230] (12) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0231] (13) Anode / Hole Injection Layer / Hole Transport Layer / Electron Blocking Layer / Light Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0232] (14) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0233] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0234] (16) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Cathode

[0235] (17) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode

[0236] (18) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode / Capping Layer

[0237] (19) Anode / Hole Injection Layer / First Hole Transport Layer / Second Hole Transport Layer / Light Emitting Layer / Hole Blocking Layer / Electron Transport Layer / Electron Injection Layer / Cathode / Covering Layer

[0238] The organic light-emitting device of the present invention can have the following structure: Figure 1 and Figure 2 The structure shown is not limited to this.

[0239] Figure 1 The diagram illustrates the structure of an organic light-emitting device in which a substrate 1, an anode 2, an organic layer 3, and a cathode 10 are sequentially stacked. In the structure described above, the compound of chemical formula 1 may be included in the organic layer 3.

[0240] Figure 2The diagram illustrates the structure of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 4, a hole transport layer 5, an electron blocking layer 100, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 10. In the structure described above, the compound of chemical formula 1 may be included in the electron blocking layer 100.

[0241] In one embodiment of the present invention, the above-mentioned organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0242] In one embodiment of the present invention, the above-mentioned organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0243] In this invention, when it is stated that a certain component is located "on" another component, it includes not only the case where the component is connected to the other component, but also the case where there are other components between the two components.

[0244] In this invention, when it is stated that a part "includes / contains" a certain constituent element, unless otherwise stated, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0245] In this invention, the term "layer" is used interchangeably with "film" primarily used in this technical field, referring to a coating covering the target area. The size of the "layer" is not limited; the sizes of each "layer" can be the same or different. In one embodiment, the size of a "layer" can be equal to the size of the entire device, equivalent to the size of a specific functional area, or as small as a single sub-pixel.

[0246] In this invention, the meaning of a specific substance A being contained in layer B includes i) the case where one or more substances A are contained in a single layer of layer B, and ii) the case where layer B is composed of one or more layers and substances A are contained in one or more layers of multi-layered layer B.

[0247] In this invention, the meaning of a specific substance A being contained in layer C or layer D includes all cases where it is contained in layer C or more than one layer, or ii) it is contained in layer D or more than one layer, or iii) it is contained in layer C or more than one layer and layer D or more than one layer respectively.

[0248] In one embodiment of the present invention, the light-emitting layer comprises a substrate and a dopant. The substrate and dopant used in the light-emitting layer can be materials known in the art.

[0249] In one embodiment of the present invention, the dopant includes a phosphorescent dopant or a fluorescent dopant. The fluorescent dopant may comprise arylamine compounds or boron compounds known in the art, but is not limited thereto.

[0250] In one embodiment of the present invention, the organic layer further comprises one or more n-type dopants selected from alkali metals and alkaline earth metals.

[0251] When organoalkali metal compounds or organoalkaline earth metal compounds are used as n-type dopants, they can ensure the stability of holes from the emitting layer, thereby improving the lifetime of organic light-emitting devices. Furthermore, the electron mobility of the electron transport layer and the proportion of organoalkali metal compounds or organoalkaline earth metal compounds can be adjusted to maximize the balance of holes and electrons in the emitting layer, thereby increasing luminous efficiency.

[0252] In this invention, LiQ is more preferably used as the n-type dopant for the organic layer.

[0253] According to one embodiment of the present invention, the above-described organic light-emitting device can be a series structure of two or more independent devices connected in series. In one embodiment, the series structure can be a configuration in which the respective organic light-emitting devices are bonded together by a charge-generating layer. Based on the same brightness, the devices in the series structure can be driven at lower currents compared to a single device, thus offering the advantage of significantly improved device lifetime characteristics.

[0254] According to one embodiment of the present invention, the organic layer comprises: a first stack comprising one or more light-emitting layers; a second stack comprising one or more light-emitting layers; and a charge-generating layer comprising one or more layers disposed between the first stack and the second stack.

[0255] According to another embodiment of the present invention, the organic layer comprises: a first stack comprising one or more light-emitting layers; a second stack comprising one or more light-emitting layers; and a third stack comprising one or more light-emitting layers, wherein one or more charge-generating layers are each included between the first stack and the second stack, and between the second stack and the third stack.

[0256] In this invention, the charge generating layer refers to a layer that generates holes and electrons when a voltage is applied. This charge generating layer can be an N-type charge generating layer or a P-type charge generating layer. In this invention, an N-type charge generating layer is one positioned closer to the anode than a P-type charge generating layer, and a P-type charge generating layer is one positioned closer to the cathode than an N-type charge generating layer.

[0257] The aforementioned N-type charge generation layer and P-type charge generation layer can be connected together to form an NP junction. Through the NP junction, holes are easily formed in the P-type charge generation layer, and electrons are easily formed in the N-type charge generation layer. Electrons are transported towards the anode through the LUMO energy level of the N-type charge generation layer, while holes are transported towards the cathode through the HOMO energy level of the P-type organic layer.

[0258] The first stack, the second stack, and the third stack each include one or more light-emitting layers, and may further include one or more of the following: a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a layer that simultaneously performs hole transport and hole injection (hole injection and transport layer), and a layer that simultaneously performs electron transport and electron injection (electron injection and transport layer).

[0259] In addition to containing the aforementioned compounds, the organic layer of the organic light-emitting device of the present invention can be manufactured using materials and methods known in the art.

[0260] For example, the organic light-emitting device of the present invention can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer on the anode, including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, or an electron injection layer; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate. However, the manufacturing method is not limited to this.

[0261] In addition, when manufacturing organic light-emitting devices, compounds can be deposited using not only vacuum evaporation but also solution coating to form organic layers. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0262] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. For example, metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited to these.

[0263] As the cathode material mentioned above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Examples include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0264] The aforementioned light-emitting layer may contain a host material and a dopant material.

[0265] The main materials mentioned above include aromatic fused-ring derivatives or heterocyclic compounds. Specifically, as aromatic fused-ring derivatives, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; as heterocyclic compounds, there are dibenzofuran derivatives and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0266] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amine groups, such as pyrene, anthracene, etc., which have aryl amine groups. Diindrone pyrene, etc. Furthermore, styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. Furthermore, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0267] The hole injection layer described above is a layer that receives holes from the electrode. The hole injection material is preferably a material that has the ability to transport holes, the effect of receiving holes from the anode, and an excellent hole injection effect on the light-emitting layer or light-emitting material. Furthermore, it is preferably a material with excellent ability to prevent excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material. It is also preferably a material with excellent thin film forming ability. Furthermore, the HOMO of the hole injection material is preferably between that of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds; hexanitrile hexaazabenzophenanthrene-based organic compounds; quinacridone-based organic compounds; perylene-based organic compounds; anthraquinone, polyaniline, and polythiophene-based conductive polymers.

[0268] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. It can be a single layer or a multilayer structure with two or more layers. The hole transport material is a substance capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer, preferably a substance with high hole mobility. Specific examples include arylamine-based organic compounds, carbazole-based compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0269] The aforementioned electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, preferably a material with high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavonoid-metal complexes, but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, suitable cathode materials are typically materials with low work functions and accompanied by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, all of which are accompanied by an aluminum or silver layer.

[0270] The aforementioned electron injection layer is a layer that receives electrons from the electrodes. The preferred electron injection material is one that exhibits excellent electron transport capabilities, effectively receives electrons from the cathode, and provides excellent electron injection for the light-emitting layer or light-emitting material. Furthermore, it is preferably a material that prevents excitons generated in the light-emitting layer from migrating to the hole injection layer and possesses excellent thin-film formation capabilities. Specifically, materials such as fluorenone, anthraquinone dimethyl ether, biphenylquinone, and thiamethoxam dioxide are preferred. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0271] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, 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, but are not limited to these.

[0272] The aforementioned electron blocking layer prevents electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer, thereby improving the device's lifetime and efficiency. This electron blocking layer can be formed between the light-emitting layer and the hole injection layer, or between the light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

[0273] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed under the same conditions as the electron injection layer. The materials used as the aforementioned hole-blocking layer include... Diazole or triazole derivatives, phenanthrene-rhein derivatives, aluminum complexes, etc., but not limited to these.

[0274] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0275] One embodiment of the present invention provides an electronic device including an organic light-emitting device comprising a compound of the above-described chemical formula 1.

[0276] The aforementioned electronic devices may include, but are not limited to, all display devices such as interlayer insulating films, color filters, black matrices, outer coatings, columnar pads, passivation films, buffer coatings, insulating films for multilayer printed circuit boards, flexible copper-clad laminate cover layers, insulating films and solder resist films for multilayer printed circuit boards, OLED insulating films, thin-film transistor protective films for liquid crystal display devices, diodes for OLEDs, electrode protective films and semiconductor protective films for organic EL devices, OLED insulating films, LCD insulating films, semiconductor insulating films, solar cell modules, touch panels, display panels, etc.

[0277] Methods of implementing the invention

[0278] Hereinafter, in order to specifically illustrate the present invention, embodiments and comparative examples will be described in detail. However, the embodiments and comparative examples according to the present invention can be modified in various different forms, and should not be construed as limiting the scope of the present invention to the embodiments and comparative examples detailed below. The embodiments and comparative examples of the present invention are provided to provide a more complete explanation of this specification to those skilled in the art.

[0279] <Manufacturing Example>

[0280] Manufacturing Example 1

[0281]

[0282] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (8.20 g, 23.17 mmol) and compound a-1 (7.93 g, 23.64 mmol) were completely dissolved in 348 mL of toluene. NaOtBu (3.34 g, 34.76 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.59 g, 1.16 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 1 (12.5 g, yield: 83%).

[0283] MS[M+H] + =653

[0284] Manufacturing Example 2

[0285]

[0286] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (7.50 g, 21.20 mmol) and compound a-2 (8.33 g, 21.62 mmol) were completely dissolved in 318 mL of toluene. NaOtBu (3.06 g, 31.79 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.54 g, 1.06 mmol). The mixture was heated and stirred for 3 hours. After cooling to room temperature and filtering to remove the alkali, the toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 2 (11.8 g, yield: 79%).

[0287] MS[M+H] + =703

[0288] Manufacturing Example 3

[0289]

[0290] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (7.20 g, 20.35 mmol) and compound a-3 (9.58 g, 20.75 mmol) were completely dissolved in 305 mL of toluene. NaOtBu (2.93 g, 30.52 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.52 g, 1.02 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 3 (12.0 g, yield: 76%).

[0291] MS[M+H] + =779

[0292] Manufacturing Example 4

[0293]

[0294] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (8.00 g, 22.61 mmol) and compound a-4 (8.89 g, 23.06 mmol) were completely dissolved in 340 mL of toluene. NaOtBu (3.26 g, 33.91 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.58 g, 1.13 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 4 (13.0 g, yield: 82%).

[0295] MS[M+H] + =703

[0296] Manufacturing Example 5

[0297]

[0298] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (7.50 g, 21.20 mmol) and compound a-5 (7.47 g, 21.62 mmol) were completely dissolved in 318 mL of toluene. NaOtBu (3.06 g, 31.79 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.54 g, 1.06 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 5 (12.5 g, yield: 78%).

[0299] MS[M+H] + =753

[0300] Manufacturing Example 6

[0301]

[0302] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound B (6.80 g, 16.84 mmol) and compound a-6 (7.07 g, 17.17 mmol) were completely dissolved in 253 mL of toluene. NaOtBu (2.43 g, 25.25 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.43 g, 0.84 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 6 (9.2 g, yield: 70%).

[0303] MS[M+H] + =779

[0304] Manufacturing Example 7

[0305]

[0306] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound C (6.50 g, 16.09 mmol) and compound a-7 (6.75 g, 16.41 mmol) were completely dissolved in 240 mL of toluene. NaOtBu (2.32 g, 24.14 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.41 g, 0.80 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to produce compound 7 (7.8 g, yield: 62%).

[0307] MS[M+H] + =779

[0308] Manufacturing Example 8

[0309]

[0310] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound D (7.00 g, 17.33 mmol) and compound a-8 (6.81 g, 17.68 mmol) were completely dissolved in 260 mL of toluene. NaOtBu (2.50 g, 26.00 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.44 g, 0.87 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 8 (8.5 g, yield: 65%).

[0311] MS[M+H] + =753

[0312] Manufacturing Example 9

[0313]

[0314] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (8.00 g, 22.61 mmol) and compound a-9 (8.66 g, 23.06 mmol) were completely dissolved in 340 mL of toluene. NaOtBu (3.26 g, 33.91 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.58 g, 1.13 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 9 (11.4 g, yield: 73%).

[0315] MS[M+H] + =693

[0316] Manufacturing Example 10

[0317]

[0318] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (7.40 g, 20.91 mmol) and compound a-10 (10.40 g, 21.33 mmol) were completely dissolved in 310 mL of toluene. NaOtBu (3.01 g, 31.37 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.53 g, 1.05 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 10 (14.8 g, yield: 88%).

[0319] MS[M+H] + =805

[0320] Manufacturing Example 11

[0321]

[0322] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (8.2 g, 23.17 mmol) and compound a-11 (11.29 g, 23.64 mmol) were completely dissolved in 350 mL of toluene. NaOtBu (3.34 g, 34.76 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.59 g, 1.16 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 11 (14.50 g, yield: 79%).

[0323] MS[M+H] + =795

[0324] Manufacturing Example 12

[0325]

[0326] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (7.50 g, 21.20 mmol) and compound a-12 (8.68 g, 21.62 mmol) were completely dissolved in 320 mL of toluene. NaOtBu (3.06 g, 31.79 mmol) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0) (0.54 g, 1.06 mmol). The mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the alkali was removed by filtration. The toluene was then concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 12 (12.30 g, yield: 81%).

[0327] MS[M+H] + =719

[0328] <Example>

[0329] Example 1-1

[0330] ITO (indium tin oxide) is used as A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0331] On the ITO transparent electrode prepared in this way as the anode, compounds HI1 and HI2 are mixed in a molar ratio of 98:2. A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. A compound represented by the chemical formula HT1 is then deposited onto the hole injection layer. A hole transport layer is formed by vacuum evaporation. Then, on the aforementioned hole transport layer, a film thickness of [missing information] is applied. Compound 1 from Manufacturing Example 1 was vacuum-deposited to form an electron blocking layer. Then, on the electron blocking layer, a film thickness of [missing information] was [missing information]. A light-emitting layer is formed by vacuum evaporation of a compound represented by the chemical formula BH and a compound represented by the chemical formula BD in a weight ratio of 25:1. On the aforementioned light-emitting layer, a film thickness of... A hole-blocking layer is formed by vacuum evaporation of a compound represented by the chemical formula HB1. Next, a compound represented by the chemical formula ET1 and a compound represented by the chemical formula LiQ are vacuum evaporated onto the hole-blocking layer in a 1:1 weight ratio, thereby achieving… The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0332]

[0333] During the above process, the evaporation rate of organic matter is maintained. / seconds / second, lithium fluoride at the cathode maintains Evaporation rate of / second, aluminum maintains A vapor deposition rate of / second is achieved, while maintaining a vacuum level of 2*10 during vapor deposition. -7 Up to 5*10 -6 This led to the creation of organic light-emitting devices.

[0334] Examples 1-2 to 1-12

[0335] In Examples 1-2 to 1-12, the organic light-emitting devices were manufactured by the same method as in Example 1-1, except that the compounds described in Table 1 below were used instead of Compound 1 in Example 1-1.

[0336] Comparative Examples 1-1 to 1-8

[0337] Comparative Examples 1-1 to 1-8 used the compounds listed in Table 1 below instead of compound 1 in Example 1-1, and otherwise manufactured organic light-emitting devices by the same method as in Example 1-1. The compounds used in Table 1 below to prepare EB8 are shown below.

[0338]

[0339] When an electric current was applied to the organic light-emitting devices manufactured in Examples 1-1 to 1-12 and Comparative Examples 1-1 to 1-8 above, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[0340] [Table 1]

[0341]

[0342]

[0343] As shown in Table 1 above, according to one embodiment of the present invention, an organic light-emitting device using a compound in which an amino group is substituted at the para position of a biphenyl group and a carbazole group is substituted at the ortho position as an electron blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage, or lifetime of the organic light-emitting device.

[0344] Conversely, compounds with aryl groups substituted on the dibenzofuran group bonded to the amino group exhibit inferior characteristics in terms of driving voltage, efficiency, and stability compared to compounds according to an embodiment of the present invention. Comparative Examples 1-1 to 1-3, using the above-mentioned compounds EB1 to EB3 with biphenyl groups substituted on the dibenzofuran group bonded to the amino group, showed deteriorated characteristics compared to the examples, such as increased voltage, decreased efficiency, and reduced lifetime.

[0345] Furthermore, in Comparative Examples 1-4, which used compound EB4 in which the dibenzofuran group was not directly bonded to the amino group but was bonded through a linker such as a phenylene group, the organic light-emitting device exhibited deteriorated characteristics such as increased voltage, decreased efficiency, and reduced lifetime compared to the examples in which the dibenzofuran group and the amino group were directly bonded.

[0346] Furthermore, the organic light-emitting devices of Comparative Examples 1-4 to 1-8, which used biphenyl-amino group binding sites and biphenyl-carbazole group binding sites that were not at the para-position and ortho-position respectively according to an embodiment of the present invention, also exhibited characteristics that deteriorated compared to the examples, such as increased voltage, decreased efficiency, and decreased lifetime.

[0347] The preferred embodiment (electron blocking layer) of the present invention has been described above, but the present invention is not limited thereto. It can be implemented in various forms within the scope of the claims and the detailed description of the invention, and these variations also fall within the scope of the present invention.

Claims

1. A compound selected from any one of the following compounds:

2. An organic light-emitting device, comprising: Anode, cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises the compound of claim 1.

3. The organic light-emitting device according to claim 2, wherein, The organic layer includes one or more layers selected from hole injection layer, hole transport layer, hole injection and transport layer, and electron blocking layer.

4. The organic light-emitting device according to claim 2, wherein, The organic layer includes an electron blocking layer, which contains the compound.

5. The organic light-emitting device according to claim 2, wherein, The organic layer includes a light-emitting layer; and one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer. The compound is contained in one or more layers selected from the hole injection layer, the hole transport layer, the hole injection and transport layer, and the electron blocking layer.

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