Compounds and organic light emitting devices using the same

Abstract

The present disclosure relates to new compounds and organic light emitting devices comprising the same.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims the benefit of Korean Patent Application No. 10-2021-0023630, filed with the Korean Intellectual Property Office on February 22, 2021, and Korean Patent Application No. 10-2022-0022272, filed with the Korean Intellectual Property Office on February 21, 2022, the disclosure of which is incorporated herein by reference in its entirety.

[0003] This disclosure relates to new compounds and organic light-emitting devices incorporating them. Background Technology

[0004] Organic light emission generally refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission exhibit characteristics such as wide viewing angle, excellent contrast, fast response time, and superior brightness, driving voltage, and response speed, and have therefore been the subject of much research.

[0005] Organic light-emitting devices (OLEDs) typically have a structure comprising an anode, a cathode, and an organic material layer between the anode and cathode. The organic material layer often has a multilayer structure containing different materials to improve the efficiency and stability of the OLED. For example, the organic material layer can be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of an OLED, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state.

[0006] There is a continued need to develop new organic materials for use in organic light-emitting devices as described above.

[0007] [Existing Technical Documents]

[0008] [Patent Literature]

[0009] (Patent Document 0001) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] This disclosure relates to new compounds and organic light-emitting devices incorporating them.

[0012] Technical solution

[0013] In this disclosure, compounds represented by the following chemical formula 1 are provided:

[0014] [Chemical Formula 1]

[0015]

[0016] In chemical formula 1,

[0017] Y is either O or S.

[0018] D stands for deuterium.

[0019] L represents a single bond; C may be substituted or unsubstituted. 6-60 aryl; or substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S. 2-60 Hybrid aryl,

[0020] L1 and L2 are each independent single bonds; or C bonds that are substituted or unsubstituted. 6-60 Alpha-aryl

[0021] Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S. 2-60 heteroaryl, and

[0022] R is hydrogen; or C is unsubstituted or deuterated. 6-60 Aryl.

[0023] In addition, an organic light-emitting device is provided, the organic light-emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains a compound represented by chemical formula 1.

[0024] Beneficial effects

[0025] The compound represented by chemical formula 1 can be used as a material for the organic material layer of organic light-emitting devices, and can improve the efficiency, low driving voltage and / or lifetime of organic light-emitting devices. Attached Figure Description

[0026] Figure 1 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0027] Figure 2 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a cathode 4. Detailed Implementation

[0028] In the following sections, embodiments of the present disclosure will be described in more detail to aid in understanding the invention.

[0029] (Definition of the term)

[0030] As used in this article, symbols and This refers to a bond that is connected to another substituent.

[0031] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from: deuterium; halogen group; cyano; nitro; hydroxyl; carbonyl; ester group; imide group; amino; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group; aryl thio group; alkyl sulfonyl group; aryl sulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; arylenyl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphine group; and heteroaryl group containing at least one of N, O, and S atoms, or unsubstituted or substituted with two or more substituents linked together from the substituents exemplified above. For example, "substituents linked together from two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can also be interpreted as a substituent linked together from two phenyl groups. For example, the term "substituted or unsubstituted" can be understood as meaning "unsubstituted or selected from deuterium, halogens, C". 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 At least one substituent (e.g., 1 to 5 substituents) is substituted in the aryl group. In addition, in this disclosure, the term "substituted with at least one substituent" can be understood to mean "substituted with 1 to 5 substituents" or "substituted with 1 or 2 substituents".

[0032] In this disclosure, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably from 1 to 40. Specifically, the carbonyl group can be a substituent having the following structural formula, but is not limited thereto.

[0033]

[0034] In this disclosure, the ester group may have a structure in which the oxygen atom of the ester group is substituted by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or by an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a substituent having the following structural formulas, but is not limited thereto.

[0035]

[0036] In this disclosure, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group can be a substituent having the following structural formula, but is not limited thereto.

[0037]

[0038] In this disclosure, silanes specifically include, but are not limited to, trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc.

[0039] In this disclosure, boron group specifically includes, but is not limited to, trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, phenylboronyl, etc.

[0040] Examples of halogen groups in this disclosure include fluorine, chlorine, bromine, or iodine.

[0041] In this disclosure, the alkyl group can be straight-chain or branched, and its carbon number is not particularly limited, but is preferably from 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbons. According to another embodiment, the alkyl group has 1 to 10 carbons. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1,-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethyl Butyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, etc., but not limited to these.

[0042] In this disclosure, the alkenyl group can be straight-chain or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbons. According to another embodiment, the alkenyl group has 2 to 10 carbons. According to yet another embodiment, the alkenyl group has 2 to 6 carbons. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc.

[0043] In this disclosure, the cycloalkyl group is not particularly limited, but it is preferably composed of 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, 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.

[0044] In this disclosure, the aryl group is not particularly limited, but it is preferably composed of 6 to 60 carbon atoms, and can be an aromatic monocyclic or polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, etc. Polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, triphenylene, pyrene, perylene, etc. Basic, etc., but not limited to this.

[0045] In this disclosure, a heteroaryl group is a heteroaryl group containing at least one heteroatom selected from O, N, Si, and S as a heteroelement, and its carbon number is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furanyl, pyrroleyl, imidazolyl, thiazolyl, and others. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthrolinel, iso Azolyl, thiadiazolyl, phenthiazinyl, dibenzofuranyl, etc., but not limited to these.

[0046] In this disclosure, the aryl groups in aralkyl, arylenyl, alkylaryl, arylamino, and arylsilyl are the same as those described in the foregoing examples of aryl. In this disclosure, the alkyl groups in aralkyl, alkylaryl, and alkylamino are the same as those described in the foregoing examples of alkyl. In this disclosure, the heteroaryl groups in heteroarylamines can be described using the foregoing description of heteroaryl. In this disclosure, the alkenyl group in arylenyl is the same as those described in the foregoing examples of alkenyl. In this disclosure, the foregoing description of aryl can be applied, except that the arylene group is a divalent group. In this disclosure, the foregoing description of heteroaryl can be applied, except that the heteroarylene group is a divalent group. In this disclosure, the foregoing description of aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In this disclosure, the foregoing description of heteroaryl can be applied, except that the heterocycle is not a monovalent group but is formed by combining two substituents.

[0047] (compound)

[0048] Additionally, this disclosure provides compounds represented by chemical formula 1.

[0049] Specifically, the compound represented by Formula 1 has a structure containing a dibenzofuran / dibenzothiophene core, in which a phenyl group (phenyl-D5) substituted with five deuterium groups is substituted at the 6-position, and a triazine group is further substituted at the 3-position. Furthermore, the compound may have a structure in which the carbon at the 8-position of the dibenzofuran / dibenzothiophene is either unsubstituted or substituted with a deuterium-substituted aryl group.

[0050] In particular, compounds having a structure in which the triazine group is substituted at the 3-position of the dibenzofuran / dibenzothiophene core and the phenyl group with 5 deuterium substitutions is substituted at the 6-position of the dibenzofuran / dibenzothiophene core exhibit a CD bond energy greater than that of the CH bond. Therefore, compared to compounds without deuterium-substituted phenyl groups, they possess stronger bond energies in the molecule, thus exhibiting improved material stability. Furthermore, since deuterium is not directly substituted in the dibenzofuran / dibenzothiophene core, these compounds can exhibit higher electronic stability than compounds in which deuterium is directly substituted in the core.

[0051] Therefore, organic light-emitting devices using the above compounds can have significantly improved lifetimes.

[0052] In one implementation, L, L1, and L2 can be single bonds, or unsubstituted or deuterated C bonds. 6-20 Alpha-aryl.

[0053] Specifically, L can be a single bond.

[0054] Furthermore, L1 and L2 can each be independently a single bond or a phenylene group. In other words, L1 and L2 can each be independently a single bond, a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group.

[0055] For example, both L1 and L2 are single bonds, or

[0056] One of L1 and L2 is a single bond, and the other is 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0057] In this paper, L1 and L2 can be the same as each other. Alternatively, L1 and L2 can be different from each other.

[0058] In one implementation, Ar1 and Ar2 can each be independently unsubstituted or selected from deuterium, C 1-10 Alkyl and C 6-20 At least one substituent in the aryl group substituted C 6-20 Aryl; or unsubstituted or selected from deuterium, C 1-10 Alkyl and C 6-20 At least one substituent in the aryl group substituted for a C containing at least one heteroatom of N, O, and S. 2-60 Mixed aromatic compounds.

[0059] Specifically, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl.

[0060] Ar1 and Ar2 can be unsubstituted or substituted with at least one substituent selected from deuterium, methyl and phenyl.

[0061] More specifically, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl.

[0062] Ar1 and Ar2 can be unsubstituted or substituted with 1 to 5 substituents selected from deuterium, methyl and phenyl.

[0063] For example, Ar1 and Ar2 can each be independently selected from any of the following, but are not limited to:

[0064]

[0065] In this paper, Ar1 and Ar2 can be the same as each other. Alternatively, Ar1 and Ar2 can be different from each other.

[0066] In one implementation, at least one of Ar1 and Ar2 can be unsubstituted or deuterated C. 6-12 Aryl.

[0067] For example, at least one of Ar1 and Ar2 can be or

[0068]

[0069] In one implementation, R can be hydrogen, or unsubstituted or deuterated C. 6-20 Aryl.

[0070] More specifically, R can be hydrogen, an unsubstituted or deuterated phenyl group, an unsubstituted or deuterated biphenyl group, or an unsubstituted or deuterated naphthyl group.

[0071] In other words, R can be hydrogen, an unsubstituted or 1 to 5 deuterated phenyl group, an unsubstituted or 1 to 9 deuterated biphenyl group, or an unsubstituted or 1 to 7 deuterated naphthyl group.

[0072] For example, R can be hydrogen,

[0073] In one embodiment, when R is not hydrogen, that is, when R is unsubstituted or deuterated C 6-60 In the case of aryl, R can be the same as Ar1 or Ar2.

[0074] In one embodiment, the compound may be represented by any of the following chemical formulas 1-1 to 1-5:

[0075] [Chemical Formula 1-1]

[0076]

[0077] [Chemical Formula 1-2]

[0078]

[0079] [Chemical Formulas 1-3]

[0080]

[0081] [Chemical Formulas 1-4]

[0082]

[0083] [Chemical Formulas 1-5]

[0084]

[0085] In chemical formulas 1-1 to 1-5,

[0086] Y, L1, L2, Ar1, and Ar2 are as defined in chemical formula 1.

[0087] Meanwhile, representative examples of compounds represented by chemical formula 1 are as follows:

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] Meanwhile, the compound represented by chemical formula 1 can be prepared by, for example, the preparation method shown in reaction scheme 1 below.

[0109] [Reaction Scheme 1]

[0110]

[0111] In reaction scheme 1, X is a halogen, preferably bromine or chlorine, and the restrictions on other substituents are the same as described above.

[0112] Specifically, the compound represented by Formula 1 can be prepared by a Suzuki coupling reaction of reactants A1 and A2. The Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used in the Suzuki coupling reaction can be appropriately modified. The preparation method can be described in more detail in the preparation examples below.

[0113] (Organic light-emitting devices)

[0114] Furthermore, according to another aspect of this disclosure, an organic light-emitting device comprising the compound represented by Chemical Formula 1 is provided. As an example, an organic light-emitting device is provided, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1.

[0115] The organic material layer of the organic light-emitting device disclosed herein can have a single-layer structure, or it can have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of this disclosure can have a structure that includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it can include a small number of organic material layers.

[0116] In one embodiment, the organic material layer may include a light-emitting layer, wherein the organic material layer containing the above compounds may be a light-emitting layer.

[0117] In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, wherein the organic material layer containing the above compounds may be a light-emitting layer or an electron transport layer.

[0118] In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, and an electron injection layer, wherein the organic material layer containing the above compounds may be a light-emitting layer or an electron transport layer.

[0119] In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the organic material layer containing the above compounds may be a light-emitting layer or an electron transport layer.

[0120] The organic material layer of the organic light-emitting device disclosed herein may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of this disclosure may have a structure that, in addition to the light-emitting layer, includes a hole injection layer and a hole transport layer disposed between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer disposed between the light-emitting layer and the second electrode. However, the structure of the organic light-emitting device is not limited to this, and it may include a small number of organic material layers or a large number of organic material layers.

[0121] Furthermore, the organic light-emitting device according to this disclosure can be a normal type organic light-emitting device in which, when the first electrode is the anode and the second electrode is the cathode, the anode, one or more organic material layers, and the cathode are sequentially stacked on a substrate. Alternatively, the organic light-emitting device according to this disclosure can be an inverted type organic light-emitting device in which, when the first electrode is the cathode and the second electrode is the anode, the cathode, one or more organic material layers, and the anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of this disclosure is as follows: Figure 1 and Figure 2 As shown in the image.

[0122] Figure 1 An example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 is shown. In such a structure, a compound represented by chemical formula 1 can be contained in the light-emitting layer.

[0123] Figure 2 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a cathode 4. In such a structure, a compound represented by chemical formula 1 may be included in the light-emitting layer.

[0124] Organic light-emitting devices according to this disclosure can be manufactured using materials and methods known in the art, except that at least one of the organic material layers comprises a compound represented by Chemical Formula 1. Furthermore, when the organic light-emitting device comprises a plurality of organic material layers, the organic material layers can be formed from the same material or different materials.

[0125] For example, the organic light-emitting device according to this disclosure can be fabricated by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be fabricated by: depositing a metal, a conductive metal oxide, or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; forming an organic material layer on the anode comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer; and then depositing a material that can be used as a cathode on the organic material layer. Besides this method, the organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0126] Furthermore, in the fabrication of organic light-emitting devices, compounds represented by chemical formula 1 can be formed into organic material layers through solution coating and vacuum deposition methods. In this paper, solution coating methods refer to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, etc., but are not limited to these.

[0127] In addition to this method, organic light-emitting devices can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the fabrication method is not limited to this.

[0128] For example, the first electrode is the anode and the second electrode is the cathode, or the first electrode is the cathode and the second electrode is the anode.

[0129] As anode materials, materials with a high work function are generally preferred, allowing holes to be smoothly injected into the organic material layer. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited thereto.

[0130] As cathode materials, materials with a small work function are generally preferred, allowing electrons to be easily injected into the organic material layer. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited to these.

[0131] Furthermore, the hole injection layer is a layer used to inject holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, thus exhibiting a hole injection effect in the anode and an excellent hole injection effect on the light-emitting layer or light-emitting material, preventing excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and possessing excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline, and polythiophene-based conductive polymers.

[0132] Furthermore, the hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is suitably a material with a high hole mobility, capable of receiving holes from the anode or hole injection layer and transporting them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0133] Furthermore, the electron blocking layer is formed on the hole transport layer, preferably in contact with the light-emitting layer, and thus serves to control hole mobility, prevent excessive electron movement, and increase the likelihood of hole-electron binding, thereby improving the efficiency of the organic light-emitting device. The electron blocking layer contains an electron blocking material, and while arylamine-based organic materials can be used, it is not limited to this.

[0134] Furthermore, the luminescent layer may comprise a host material and a dopant material. As the host material, compounds represented by Formula 1 can be used. In addition to compounds represented by Formula 1, the host material may also include fused aromatic ring derivatives or heterocyclic compounds. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these.

[0135] In one embodiment, in addition to the compound represented by chemical formula 1, the light-emitting layer may also contain a compound represented by the following chemical formula 2:

[0136] [Chemical Formula 2]

[0137]

[0138] In chemical formula 2,

[0139] Ar'1 and Ar'2 are each independently substituted or unsubstituted C. 6-60 aryl, or substituted or unsubstituted C containing at least one heteroatom of N, O and S. 2-60 heteroaryl, and

[0140] R'1 and R'2 are each independently hydrogen; deuterium; C. 1-60 Alkyl; C 6-60 aryl; or C containing at least one heteroatom selected from N, O, and S. 2-60 heteroaryl; and

[0141] r and s are each an independent integer from 0 to 7.

[0142] When an organic light-emitting device also contains a compound represented by chemical formula 2, which can effectively transfer holes to the dopant material, as the host material of the light-emitting layer, the possibility of hole-electron recombination in the light-emitting layer, along with the compound represented by chemical formula 1, which has excellent electron transport capabilities, can be increased, thereby improving the efficiency and lifetime of the organic light-emitting device.

[0143] According to one embodiment, a compound represented by chemical formula 2 can be represented by chemical formula 2':

[0144] [Chemical Formula 2']

[0145]

[0146] In chemical formula 2',

[0147] Ar'1, Ar'2, R'1, R'2, r, and s are as defined in chemical formula 2.

[0148] Furthermore, in chemical formula 2, Ar'1 and Ar'2 can each independently be C. 6-20 aryl; or C containing at least one heteroatom of N, O, and S. 2-20 Mixed aromatics,

[0149] Ar'1 can be unsubstituted or selected from deuterium and C. 6-20 At least one substituent in the aryl group is substituted.

[0150] For example, Ar'1 and Ar'2 can each independently be phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl.

[0151] Ar'1 can be unsubstituted or selected from deuterium and C. 6-20 At least one substituent in the aryl group is substituted.

[0152] In this article, at least one of Ar'1 and Ar'2 can be phenyl or biphenyl.

[0153] Furthermore, in chemical formula 2, R'1 and R'2 can each be independently hydrogen, deuterium, or C. 6-20 Aryl.

[0154] For example, R'1 and R'2 can each be hydrogen, deuterium, or phenyl independently, but are not limited thereto.

[0155] Furthermore, r and s, which represent the quantities of R'1 and R'2 respectively, can be independently 0, 1, 2, 3, 4, 5, 6, or 7.

[0156] More specifically, r and s can each be 0, 1, or 7 independently.

[0157] For example, r+s can be 0 or 1.

[0158] Representative examples of compounds represented by chemical formula 2 are as follows:

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] These two host materials, the compound represented by chemical formula 1 and the compound represented by chemical formula 2, can be included in the luminescent layer in a weight ratio of 10:90 to 90:10, for example 50:50.

[0168] Dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are fused aromatic ring derivatives with aryl amino groups, either substituted or unsubstituted, and examples include pyrene, anthracene, etc., which contain aryl amino groups. Examples include benzo[a]pyrene and others. Styrene amine compounds are compounds in which at least one aryl vinyl group is substituted in a substituted or unsubstituted aryl amine, wherein one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrene amines, styrene diamines, styrene triamines, and styrene tetraamines. Furthermore, metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0169] Furthermore, a hole-blocking layer refers to a layer formed on the light-emitting layer, preferably positioned in contact with it, to control electron mobility, prevent excessive hole movement, and increase the likelihood of hole-electron binding, thereby improving the efficiency of the organic light-emitting device. The hole-blocking layer comprises a hole-blocking material, and examples of such materials include compounds incorporating electron-withdrawing groups, such as azazine-based derivatives, including triazines; triazole derivatives; Diazole derivatives; phenanthrene-rholine derivatives; phosphine oxide derivatives, but not limited to these.

[0170] Furthermore, the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer, and is formed on the light-emitting layer or hole-blocking layer. The electron transport layer contains electron transport materials, and materials with high electron mobility are suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, triazine derivatives, etc. Alternatively, it can be combined with fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, The compounds may be used together, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrone, or their derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, etc.

[0171] Furthermore, the electron injection layer is a layer that injects electrons from the electrodes and is formed on the electron transport layer. Specific examples of electron injection materials included in the electron injection layer may include LiF, NaCl, CsF, Li₂O, BaO, fluorene, anthraquinone dimethane, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones and their derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, etc., but not limited to these.

[0172] Examples of metal complex compounds include, but are not limited to, 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-hydroxyquinoline)gallium chloride, bis(2-methyl-8-hydroxyquinoline)(o-cresol)gallium, bis(2-methyl-8-hydroxyquinoline)(1-naphthol)aluminum, and bis(2-methyl-8-hydroxyquinoline)(2-naphthol)gallium.

[0173] The organic light-emitting device according to this disclosure can be a bottom-emitting device, a top-emitting device, or a dual-sided emitting device, and in particular, it can be a bottom-emitting device that requires relatively high luminous efficiency.

[0174] In addition to organic light-emitting devices, compounds represented by chemical formula 1 can also be included in organic solar cells or organic transistors.

[0175] The following examples will describe in detail the preparation of compounds represented by Formula 1 and organic light-emitting devices comprising them. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of this disclosure.

[0176] [Preparation Example]

[0177] Preparation Example 1: Preparation of Compound A-4

[0178] 1) Preparation of compound A-1

[0179]

[0180] 2-Bromo-6-iodophenol (50 g, 178.6 mmol) and (4-chloro-2-fluorophenyl)boronic acid (31.1 g, 178.6 mmol) were added to 1000 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (74.1 g, 535.8 mmol) was then dissolved in 74 mL of water and added to the mixture. After thorough stirring, tetra(triphenylphosphine)palladium (6.2 g, 5.4 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved in 1071 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound A-1 (35.4 g, 66%, MS: [M+H]) as a gray solid. + =300.9).

[0181] 2) Preparation of compound A-2

[0182]

[0183] Under a nitrogen atmosphere, A-1 (30 g, 100 mmol) and sub C (23.3 g, 100 mmol) were added to 600 mL of dimethylformamide, and the mixture was stirred and refluxed. Then, potassium triphosphate (63.7 g, 300.1 mmol) was added and stirred thoroughly. After reacting for 3 hours, the mixture was cooled to room temperature. The organic layer was then filtered to remove salts, and the filtered organic layer was distilled. It was then dissolved in 433 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare compound A-2 (29.5 g, 68%, MS: [M+H]) as a yellow solid. + =434.1).

[0184] (3) Preparation of compound A-3

[0185]

[0186] A-2 (50 g, 178.6 mmol) and phenylboronic acid-D5 (22.7 g, 178.6 mmol) were added to 1000 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (74.1 g, 535.8 mmol) was then dissolved in 74 mL of water and added to the mixture. After thorough stirring, tetra(triphenylphosphine)palladium (6.2 g, 5.4 mmol) was added. The reaction was allowed to proceed for 2 hours, then cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved in 1011 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound A-3 (34.4 g, 68%, MS: [M+H]) as a yellow solid. + =284.1).

[0187] (4) Preparation of compound A-4

[0188]

[0189] A-3 (50 g, 139.2 mmol) and bis(pinacol)diboron (38.9 g, 153.2 mmol) were added to 1000 ml of 1,4-dioxane under a nitrogen atmosphere. In an alkane, the mixture was stirred and refluxed. Potassium acetate (40.1 g, 417.7 mmol) was then added and stirred thoroughly, followed by palladium dibenzylacetone (2.4 g, 4.2 mmol) and tricyclohexylphosphine (2.3 g, 8.4 mmol). After reacting for 3 hours, the mixture was cooled to room temperature. The organic layer was then filtered to remove salts, and the filtered organic layer was distilled. It was then dissolved in 628 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethanol to prepare compound A-4 (52.8 g, 84%, MS: [M+H]) as a gray solid. + =452.2).

[0190] Preparation Example 2: Preparation of Compound B-4

[0191] 1) Preparation of compound B-2

[0192]

[0193] A-1 (50 g, 166.7 mmol) and phenylboronic acid-D5 (21.2 g, 166.7 mmol) were added to 1000 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (69.1 g, 500.1 mmol) was then dissolved in 69 mL of water and added to the mixture. After thorough stirring, tetra(triphenylphosphine)palladium (5.8 g, 5 mmol) was added. The reaction was allowed to proceed for 3 hours, then cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved in 1011 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound B-2 (38.4 g, 76%, MS: [M+H]) as a yellow solid. + =304.1).

[0194] 2) Preparation of compound B-3

[0195]

[0196] B-2 (50 g, 165 mmol) and N-bromosuccinimide (32.3 g, 181.5 mmol) were added to 250 mL of dimethylformamide under a nitrogen atmosphere and reacted for 3 h. The mixture was then cooled in an ice bath while water was added. The resulting solid was filtered. It was then dissolved in 596 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare compound B-3 (39.9 g, 67%, MS: [M+H]) as a white solid. + =362).

[0197] 2) Preparation of compound B-4

[0198]

[0199] B-3 (50 g, 131.2 mmol) was added to 250 mL of dimethylformamide, followed by potassium carbonate. The mixture was then stirred and heated to 140 °C. After reacting for 7 hours, it was cooled to room temperature, and water was added. The resulting solid was filtered. It was then dissolved in 474 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare compound B-4 (31.3 g, 66%, MS: [M+H]) as a white solid. + =362).

[0200] Preparation Example 3: Preparation of Compound C-1

[0201] 1) Preparation of compound C-1

[0202]

[0203] B-4 (50 g, 138.5 mmol) and phenylboronic acid (16.9 g, 138.5 mmol) were added to 1000 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (57.4 g, 415.5 mmol) was then dissolved in 57 mL of water and added to the mixture. After thorough stirring, tetra(triphenylphosphine)palladium (4.8 g, 4.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved in 995 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound C-1 (29.8 g, 60%, MS: [M+H]) as a white solid. + =360.1).

[0204] (2) Preparation of compound C-2

[0205]

[0206] C-1 (50 g, 139.2 mmol) and bis(pinacol)diboron (38.9 g, 153.2 mmol) were added to 1000 ml of 1,4-dioxane under a nitrogen atmosphere. In an alkane, the mixture was stirred and refluxed. Potassium acetate (40.1 g, 417.7 mmol) was then added and stirred thoroughly, followed by palladium dibenzylacetone (2.4 g, 4.2 mmol) and tricyclohexylphosphine (2.3 g, 8.4 mmol). After reacting for 4 hours, the mixture was cooled to room temperature. The organic layer was then filtered to remove salts, and the filtered organic layer was distilled. It was then dissolved in 628 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethanol to prepare compound C-2 (52.8 g, 84%, MS: [M+H]) as a gray solid. + =452.2).

[0207] Preparation Example 4: Preparation of Compound D-1

[0208] 1) Preparation of compound D-1

[0209]

[0210] B-4 (50 g, 138.5 mmol) and phenylboronic acid-D5 (17.6 g, 138.5 mmol) were added to 1000 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (57.4 g, 415.5 mmol) was then dissolved in 57 mL of water and added to the mixture. After thorough stirring, tetra(triphenylphosphine)palladium (4.8 g, 4.2 mmol) was added. The reaction was allowed to proceed for 2 hours, then cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved in 1009 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound D-1 (30.3 g, 60%, MS: [M+H]) as a white solid. + =365.1).

[0211] 2) Preparation of compound D-2

[0212]

[0213] D-1 (50 g, 139.2 mmol) and bis(pinacol)diboron (38.9 g, 153.2 mmol) were added to 1000 ml of 1,4-dioxane under a nitrogen atmosphere. In an alkane, the mixture was stirred and refluxed. Potassium acetate (40.1 g, 417.7 mmol) was then added and stirred thoroughly, followed by palladium dibenzylacetone (2.4 g, 4.2 mmol) and tricyclohexylphosphine (2.3 g, 8.4 mmol). After reacting for 3 hours, the mixture was cooled to room temperature. The organic layer was then filtered to remove salts, and the filtered organic layer was distilled. It was then dissolved in 635 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethanol to prepare compound D-2 (42.6 g, 67%, MS: [M+H]) as a gray solid. + =457.2).

[0214] Preparation Example 5: Preparation of Compound E-1

[0215] 1) Preparation of compound E-1

[0216]

[0217] B-4 (50 g, 138.5 mmol) and [1,1'-biphenyl]-4-ylboronic acid (27.4 g, 138.5 mmol) were added to 1000 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (57.4 g, 415.5 mmol) was then dissolved in 57 mL of water and added to the mixture. After thorough stirring, tetra(triphenylphosphine)palladium (4.8 g, 4.2 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved in 1205 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound E-1 (32.5 g, 54%, MS: [M+H]) as a white solid. + =436.1).

[0218] 2) Preparation of compound E-2

[0219]

[0220] E-1 (50 g, 114.9 mmol) and bis(pinacol)diboron (32.1 g, 126.4 mmol) were added to 1000 ml of 1,4-dioxane under a nitrogen atmosphere. In an alkane, the mixture was stirred and refluxed. Potassium acetate (33.1 g, 344.7 mmol) was then added and stirred thoroughly, followed by palladium dibenzylacetone (2 g, 3.4 mmol) and tricyclohexylphosphine (1.9 g, 6.9 mmol). After reacting for 5 hours, the mixture was cooled to room temperature. The organic layer was then filtered to remove salts, and the filtered organic layer was distilled. It was then dissolved in 606 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethanol to prepare compound E-2 (43 g, 71%, MS: [M+H]) as a gray solid. + =528.3).

[0221] Preparation Example 6: Preparation of Compound F-1

[0222] 1) Preparation of compound F-1

[0223]

[0224] B-4 (50 g, 138.5 mmol) and naphth-2-ylboronic acid (23.8 g, 138.5 mmol) were added to 1000 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (57.4 g, 415.5 mmol) was then dissolved in 57 mL of water and added to the mixture. After thorough stirring, tetra(triphenylphosphine)palladium (4.8 g, 4.2 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved in 1133 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound F-1 (43.6 g, 77%, MS: [M+H]) as a white solid. + =410.1).

[0225] 2) Preparation of compound F-2

[0226]

[0227] F-1 (50 g, 168.9 mmol) and bis(pinacol)diboron (47.2 g, 185.8 mmol) were added to 1000 ml of 1,4-dioxane under a nitrogen atmosphere. In an alkane, the mixture was stirred and refluxed. Potassium acetate (48.7 g, 506.7 mmol) was then added and stirred thoroughly, followed by palladium dibenzylacetone (2.9 g, 5.1 mmol) and tricyclohexylphosphine (2.8 g, 10.1 mmol). After reacting for 7 hours, the mixture was cooled to room temperature. The organic layer was then filtered to remove salts, and the filtered organic layer was distilled. It was then dissolved in 661 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethanol to prepare compound F-2 (42.9 g, 65%, MS: [M+H]) as a gray solid. + =392.2).

[0228] Preparation Example 7: Preparation of Compound G-2

[0229] 1) Preparation of compound G-1

[0230]

[0231] 3-Chloro-6-iododibenzo[b,d]thiophene (50 g, 145.4 mmol) and phenylboronic acid-D5 (18.5 g, 145.4 mmol) were added to 1000 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (60.3 g, 436.2 mmol) was then dissolved in 60 mL of water and added to the mixture. After thorough stirring, tetra(triphenylphosphine)palladium (5 g, 4.4 mmol) was added. The reaction was allowed to proceed for 2 hours, then cooled to room temperature. The organic layer was then separated from the aqueous layer and distilled. It was then dissolved in 861 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound G-1 (28.8 g, 67%, MS: [M+H]) as a white solid. + =297.1).

[0232] 2) Preparation of compound G-2

[0233]

[0234] G-1 (50 g, 168.9 mmol) and bis(pinacol)diboron (47.2 g, 185.8 mmol) were added to 1000 ml of 1,4-dioxane under a nitrogen atmosphere. In an alkane, the mixture was stirred and refluxed. Potassium acetate (48.7 g, 506.7 mmol) was then added and stirred thoroughly, followed by palladium dibenzylacetone (2.9 g, 5.1 mmol) and tricyclohexylphosphine (2.8 g, 10.1 mmol). After reacting for 3 hours, the mixture was cooled to room temperature. The organic layer was then filtered to remove salts, and the filtered organic layer was distilled. It was then dissolved in 661 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethanol to prepare compound G-2 (50.9 g, 77%, MS: [M+H]) as a gray solid. + =392.2).

[0235] Synthesis Example 1: Preparation of Compound 1

[0236]

[0237] A-4 (20 g, 53.3 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (14.2 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra-triphenylphosphine palladium (1.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1280 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 1 (18.2 g, 71%, MS: [M+H]) as a white solid. + =481.2).

[0238] Synthesis Example 2: Preparation of Compound 2

[0239]

[0240] A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetratriphenylphosphine palladium (1.8 g, 1.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1482 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 2 (17.8 g, 60%, MS: [M+H]) as a white solid. + =557.2).

[0241] Synthesis Example 3: Preparation of Compound 3

[0242]

[0243] A-4 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetratriphenylphosphine palladium (1.8 g, 1.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1482 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 3 (19.6 g, 66%, MS: [M+H]) as a white solid. + =557.2).

[0244] Synthesis Example 4: Preparation of Compound 4

[0245]

[0246] A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1520 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 4 (16.7 g, 55%, MS: [M+H]) as a white solid. + =571.2).

[0247] Synthesis Example 5: Preparation of Compound 5

[0248]

[0249] A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]thiophene-4-yl)-6-phenyl-1,3,5-triazine (19.9 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1562 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 5 (17.2 g, 55%, MS: [M+H]) as a white solid. + =587.2).

[0250] Synthesis Example 6: Preparation of Compound 6

[0251]

[0252] A-4 (20 g, 53.3 mmol) and 2-chloro-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine (16.9 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1413 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 6 (17.5 g, 62%, MS: [M+H]) as a white solid. + =531.2).

[0253] Synthesis Example 7: Preparation of Compound 7

[0254]

[0255] A-4 (20 g, 53.3 mmol) and 2-chloro-4-(4-(naphth-1-yl)phenyl)-6-phenyl-1,3,5-triazine (21 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1616 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 7 (24.2 g, 75%, MS: [M+H]) as a white solid. + =607.3).

[0256] Synthesis Example 8: Preparation of Compound 8

[0257]

[0258] A-4 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1520 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 8 (17.6 g, 58%, MS: [M+H]) as a white solid. + =571.2).

[0259] Synthesis Example 9: Preparation of Compound 9

[0260]

[0261] Under a nitrogen atmosphere, C-2 (20 g, 44.3 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.2 g, 44.3 mmol) were added to 400 mL of tetrahydrofuran, and the mixture was stirred and refluxed. Potassium carbonate (18.4 g, 133 mmol) was then dissolved in 18 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.5 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1401 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was then dissolved in 1698 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 11 (20.4 g, 60%, MS: [M+H)) as a white solid. + =638.3).

[0262] Synthesis Example 10: Preparation of Compound 10

[0263]

[0264] D-2 (20 g, 43.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.7 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.2 g, 131.5 mmol) was then dissolved in 18 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.5 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1329 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 10 (19.1 g, 72%, MS: [M+H]) as a white solid. + =607.3).

[0265] Synthesis Example 11: Preparation of Compound 11

[0266]

[0267] D-2 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetratriphenylphosphine palladium (1.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1698 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 11 (20.4 g, 60%, MS: [M+H]) as a white solid. + =638.3).

[0268] Synthesis Example 12: Preparation of Compound 12

[0269]

[0270] D-2 (20 g, 53.3 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (18.3 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetratriphenylphosphine palladium (1.8 g, 1.6 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1736 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 12 (24.6 g, 71%, MS: [M+H]) as a white solid. + =652.3).

[0271] Synthesis Example 13: Preparation of Compound 13

[0272]

[0273] D-2 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1778 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 13 (19.6 g, 55%, MS: [M+H]) as a white solid. + =668.3).

[0274] Synthesis Example 14: Preparation of Compound 14

[0275]

[0276] D-2 (20 g, 53.3 mmol) and 2-chloro-4-(dibenzo[b,d]thiophene-4-yl)-6-phenyl-1,3,5-triazine (19 g, 53.3 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (22.1 g, 159.9 mmol) was then dissolved in 22 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1778 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 14 (24.9 g, 70%, MS: [M+H]) as a white solid. + =668.3).

[0277] Synthesis Example 15: Preparation of Compound 15

[0278]

[0279] D-2 (20 g, 43.8 mmol) and 2-chloro-4-(naphth-2-yl)-6-phenyl-1,3,5-triazine (13.9 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (18.2 g, 131.5 mmol) was then dissolved in 18 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.5 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1340 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 15 (18 g, 67%, MS: [M+H]) as a white solid. + =612.3).

[0280] Synthesis Example 16: Preparation of Compound 16

[0281]

[0282] D-2 (20 g, 43.8 mmol) and 2-chloro-4-(4-naphth-1-yl)phenyl)-6-phenyl-1,3,5-triazine (17.2 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred and refluxed. Potassium carbonate (18.2 g, 131.5 mmol) was then dissolved in 18 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.5 g, 1.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1507 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 16 (23.8 g, 79%, MS: [M+H]) as a white solid. + =688.7).

[0283] Synthesis Example 17: Preparation of Compound 17

[0284]

[0285] D-2 (20 g, 43.8 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (15.7 g, 43.8 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred and refluxed. Potassium carbonate (18.2 g, 131.5 mmol) was then dissolved in 18 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.5 g, 1.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was then dissolved in 1427 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 17 (21.7 g, 76%, MS: [M+H]) as a white solid. + =652.3).

[0286] Synthesis Example 18: Preparation of Compound 18

[0287]

[0288] E-2 (20 g, 37.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.1 g, 37.9 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (15.7 g, 113.8 mmol) was then dissolved in 16 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra-triphenylphosphine palladium (1.3 g, 1.1 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1199 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 18 (16.8 g, 70%, MS: [M+H]) as a white solid. + =633.3).

[0289] Synthesis Example 19: Preparation of Compound 19

[0290]

[0291] F-2 (20 g, 39.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (10.7 g, 39.9 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (16.5 g, 119.7 mmol) was then dissolved in 17 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra-triphenylphosphine palladium (1.4 g, 1.2 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1209 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 19 (18.4 g, 76%, MS: [M+H]) as a white solid. + =607.3).

[0292] Synthesis Example 20: Preparation of Compound 20

[0293]

[0294] G-2 (20 g, 51.1 mmol) and 2-chloro-4-(dibenzo[b,d]thiophene-4-yl)-6-phenyl-1,3,5-triazine (19.1 g, 51.1 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (21.2 g, 153.4 mmol) was then dissolved in 21 mL of water and added to the mixture. The mixture was then stirred thoroughly, and tetra(triphenylphosphine)palladium (1.8 g, 1.5 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was then dissolved in 1539 mL of chloroform and washed twice with water. The organic layer was then separated, treated with anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized using chloroform and ethyl acetate to prepare compound 20 as a white solid (21.9 g, 71%, MS: [M+H)). + =603.2).

[0295] Example 1: Fabrication of Organic Light-Emitting Devices

[0296] It is coated with a thickness of The ITO (indium tin oxide) glass substrate, used as the thin film, was immersed in distilled water containing a cleaning agent and ultrasonically cleaned. A product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice by a filter manufactured by Millipore Co. was used as the distilled water. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes each time with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with isopropanol, acetone, and methanol solvents, 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 depositor.

[0297] The following compound HI-1 was thermally vacuum deposited onto the prepared ITO transparent electrode. The thickness is adjusted to form a hole injection layer. Then, the following compound HT-1 is thermally vacuum deposited onto the hole injection layer. The thickness is increased to form a hole transport layer. The following compound HT-2 is vacuum-deposited onto the hole transport layer to... The thickness is such that an electron blocking layer is formed.

[0298] Compound 1 prepared in Synthesis Example 1, compound YGH-1, and phosphorescent dopant YGD-1 were co-deposited on an HT-2 deposition film in a weight ratio of 44:44:12 to form a film with a thickness of [missing information]. The luminescent layer.

[0299] The following compounds, ET-1 to 1, were vacuum deposited on the luminescent layer. The thickness is such that an electron transport layer is formed, and the following compounds, ET-2 and LiF, are vacuum deposited on the electron transport layer at a weight ratio of 98:2 to form a thickness of... The electron injection layer. Aluminum is deposited on the electron injection layer to... The thickness is used to form the cathode.

[0300]

[0301] In the above process, the deposition rate of organic materials is maintained at / seconds / second, maintaining the aluminum deposition rate at / second, and maintaining a vacuum level of 5 × 10 during deposition. -8 Up to 1×10 -7 Entrust.

[0302] Examples 2 to 20

[0303] The organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of compound 1 of Synthesis Example 1 as one of the main materials of the light-emitting layer.

[0304] At this point, the structures of the compounds used in Examples 1 to 20 are as follows.

[0305]

[0306]

[0307] Comparative Examples 1 to 5

[0308] An organic light-emitting device was manufactured in the same manner as in Example 1, except that compounds shown in Table 1 were used instead of compound 1 from Synthesis Example 1 as one of the host materials for the light-emitting layer. In this case, compounds CE1 to CE5 shown in Table 1 are as follows.

[0309]

[0310] Experiment Example 1: Evaluation of Device Characteristics

[0311] For the organic light-emitting devices prepared in the examples and comparative examples, by applying 10mA / cm 2 The current density was measured for voltage and efficiency, and this was achieved by applying 50 mA / cm². 2 The current density was used to measure the lifetime. The results are then shown in Table 1 below. In this paper, LT95 refers to the time taken until the initial brightness decreased to 95%.

[0312] [Table 1]

[0313]

[0314] As shown in Table 1, it was determined that, compared to the comparative examples using organic light-emitting devices with compounds having different structures, the organic light-emitting devices of the embodiments using compounds represented by Chemical Formula 1 as the host material of the light-emitting layer exhibited significantly improved lifetime without reducing efficiency. Therefore, considering...

[0315] Considering that there is usually a trade-off between luminous efficiency and lifetime in organic light-emitting devices, it can be determined that the compounds of this disclosure can improve the characteristics of organic light-emitting devices compared with the compounds of comparative examples.

[0316] [Explanation of reference numerals in the attached figures]

[0317] 1: Substrate 2: Anode

[0318] 3: Light-emitting layer 4: Cathode

[0319] 5: Hole injection layer; 6: Hole transport layer

[0320] 7: Electron blocking layer; 8: Electron transport layer

[0321] 9: Electron injection layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, Y is either O or S. D stands for deuterium. L represents a single bond. L1 is a single bond; or a substituted or unsubstituted C bond. 6-60 Alpha-aryl Ar1 is C with or without substitution. 6-60 Aryl, L2 is a single bond. Ar2 can be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, dibenzothiopheneyl, or carbazoleyl, and Ar2 is either unsubstituted or substituted with at least one substituent selected from deuterium, methyl, and phenyl, and R is hydrogen; or C is unsubstituted or deuterated. 6-60 Aryl, and The term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from deuterium, halogen, alkyl, and aryl, or unsubstituted or substituted with two or more substituents linked together. The condition is that the following compounds are not included:

2. The compound according to claim 1, L1 is a single bond or a phenylene oxide.

3. The compound according to claim 1, Ar1 is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, or fluorenyl, and Ar1 is either unsubstituted or substituted with at least one substituent selected from deuterium, methyl, and phenyl.

4. The compound according to claim 1, Ar1 is selected from any of the following: Ar2 is selected from any of the following:

5. The compound according to claim 1, At least one of Ar1 and Ar2 is unsubstituted or deuterated C. 6-12 Aryl.

6. The compound according to claim 1, Where R is hydrogen; an unsubstituted or deuterated phenyl group; an unsubstituted or deuterated biphenyl group; or an unsubstituted or deuterated naphthyl group.

7. The compound according to claim 6, Where R is hydrogen, 8. The compound according to claim 1, The compound described herein is represented by any one of the following chemical formulas 1-1 to 1-5: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] In the chemical formulas 1-1 to 1-5, Y, L1, L2, Ar1 and Ar2 are as defined in claim 1.

9. The compound according to claim 1, The compound mentioned is selected from any of the following compounds:

10. An organic light-emitting device, comprising: First electrode; A second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains a compound according to any one of claims 1 to 9.

11. The organic light-emitting device according to claim 10, The organic material layer containing the compound is a light-emitting layer.

12. The organic light-emitting device according to claim 11, The light-emitting layer further comprises a compound represented by the following chemical formula 2: [Chemical Formula 2] In the chemical formula 2, Ar'1 and Ar'2 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing at least one heteroatom selected from N, O, and S. 2-60 heteroaryl, and R'1 and R'2 are each independently hydrogen; deuterium; C. 1-60 Alkyl; C 6-60 aryl; or C containing at least one heteroatom selected from N, O, and S. 2-60 heteroaryl; and r and s are each an independent integer from 0 to 7.

13. The organic light-emitting device according to claim 12, The compound represented by chemical formula 2 is selected from any of the following compounds:

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