Organic light-emitting device

Abstract

The present invention provides an organic light emitting device with improved driving voltage, efficiency and lifetime.

Description

[Technical field]

[0001] [CROSS REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0177475 filed December 16, 2022 and Korean Patent Application No. 10-2023-0181045 filed December 13, 2023, and all contents disclosed in the documents of said Korean patent applications are incorporated herein by reference.

[0002] The present invention relates to an organic light emitting device with improved driving voltage, efficiency and lifetime. [Background technology]

[0003] In general, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. Organic light emitting devices using organic light emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and are excellent in brightness, driving voltage, and response speed characteristics, so much research is being conducted.

[0004] An organic light emitting device generally has a structure including a positive electrode, a negative electrode, and an organic layer between the positive electrode and the negative electrode. The organic layer is often a multi-layer structure composed of different materials to improve the efficiency and safety of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light emitting device structure, when a voltage is applied between the two electrodes, holes are injected into the organic layer at the positive electrode and electrons are injected into the organic layer at the negative electrode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0005] There is a continuous demand for the development of new organic materials for use in the above-mentioned organic light-emitting devices. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Korean Patent No. 10-2000-0051826 Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention relates to an organic light emitting device with improved driving voltage, efficiency and lifetime. [Means for solving the problem]

[0008] The present invention provides an organic light-emitting device comprising: a positive electrode; a light-emitting layer; and a negative electrode, The light-emitting layer contains a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: Organic light-emitting devices: [ka]

[0009] In the above Chemical Formula 1, Ar1 and Ar2 each independently represent a substituted or unsubstituted C 6-60 aryl; or C containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S 2-60 is heteroaryl, Ar3 is a substituted or unsubstituted C 6-60 is aryl, L is a single bond; substituted or unsubstituted C 6-60 arylene; or C containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S 2-60 Heteroarylene, R1 and R2 are each independently hydrogen or deuterium; R3 is hydrogen, deuterium, or substituted or unsubstituted C 6-60 is aryl, At least one of R2 and R3 is deuterium; a is an integer from 0 to 3; b is an integer equal to 7; [ka] In the above Chemical Formula 2, Ar4 and Ar5 each independently represent a substituted or unsubstituted C 6-60 aryl; or C containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S 2-60 is heteroaryl, R4 to R6 are each independently hydrogen or deuterium; c and e are integers from 0 to 4; d is an integer from 0 to 2. Effect of the Invention

[0010] The organic light-emitting device includes the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 in the light-emitting layer, thereby improving efficiency, lowering driving voltage, and / or improving life characteristics of the organic light-emitting device. [Brief description of the drawings]

[0011] [Figure 1] FIG. 1 is a diagram showing an example of an organic light-emitting device composed of a substrate 1, a positive electrode 2, a light-emitting layer 3 and a negative electrode 4. [Diagram 2] FIG. 1 shows an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, an electron blocking layer 8, an emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a negative electrode 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention will now be described in more detail for the sake of understanding.

[0013] In this specification, [ka] denotes a bond that is connected to another substituent.

[0014] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthiooxy group; arylthiooxy group; alkylsulfoxy group; arylsulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphine group; or heterocyclic group containing one or more of N, O and S atoms, or that the group is substituted or unsubstituted with two or more of the above-mentioned examples of the substituents linked together. For example, the "substituent with two or more substituents linked together" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent with two phenyl groups linked together. For example, the term "substituted or unsubstituted" means "unsubstituted or unsubstituted with deuterium, halogen, C 1-10 Alkyl, C 1-10 Alkoxy, C 6-20 Aryl and C containing one or more heteroatoms of N, O and S 2-20 In the present specification, the term "substituted with one or more substituents" can be understood to mean, for example, "substituted with 1 to 5 substituents" or "substituted with 1 or 2 substituents".

[0015] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may be a substituent having the following structure, but is not limited thereto. [ka]

[0016] In this specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the substituent may be one of the following structural formulas, but is not limited thereto. [ka]

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

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

[0019] In this specification, specific examples of the boron group include a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, and a phenyl boron group, but are not limited to these.

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

[0021] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

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

[0023] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and 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 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, and cyclooctyl.

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

[0025] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to this.

[0026] In this specification, the heterocyclic group is a heterocyclic group containing one or more hetero elements selected from O, N, Si and S, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of heterocyclic groups include, but are not limited to, a thiophene base, a furan base, a pyrrole base, an imidazole base, a thiazole base, an oxazole base, an oxadiazole base, a triazole base, a pyridyl base, a bipyridyl base, a pyrimidine base, a triazine base, an acridyl base, a pyridazine base, a pyrazinyl base, a quinolinyl base, a quinazoline base, a quinoxalinyl base, a phthalazinyl base, a pyridopyrimidinyl base, a pyridopyrazinyl base, a pyrazinopyrazinyl base, an isoquinoline base, an indole base, a carbazole base, a benzoxazole base, a benzimidazole base, a benzothiazole base, a benzocarbazole base, a benzothiophene base, a dibenzothiophene base, a benzofuranyl base, a phenanthroline base, an isoxazolyl base, a thiadiazolyl base, a phenothiazinyl base, and a dibenzofuranyl base.

[0027] In this specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the above-mentioned aryl group examples. In this specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-mentioned alkyl group examples. In this specification, the heteroaryl in the heteroarylamine can be applied to the above-mentioned heterocyclic group explanation. In this specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group examples.

[0028] In this specification, the above-mentioned explanation regarding the aryl group can be applied, except that the arylene is a divalent group. In this specification, the above-mentioned explanation regarding the heterocyclic group can be applied, except that the heteroarylene is a divalent group. In this specification, the above-mentioned explanation regarding the aryl group or cycloalkyl group can be applied, except that the hydrocarbon ring is not a monovalent group, but is formed by bonding two substituents. In this specification, the above-mentioned explanation regarding the heterocyclic group can be applied, except that the heterocycle is not a monovalent group, but is formed by bonding two substituents.

[0029] The present invention will be described in detail below for each component.

[0030] Positive and negative electrodes The positive electrode and the negative electrode used in the present invention refer to electrodes used in an organic light-emitting device.

[0031] The cathode material is preferably a material having a large work function so that holes can be easily injected into the organic layer.Specific examples of the cathode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0032] The negative electrode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0033] Hole injection layer The organic light emitting device according to the present invention may further include a hole injection layer on the anode, if necessary.

[0034] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect at the positive electrode, has an excellent hole injection effect on the light emitting layer or light emitting material, prevents the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer.

[0035] Specific examples of the hole injection material include, but are not limited to, metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers.

[0036] Hole transport layer The organic light-emitting device according to the present invention may optionally include a hole transport layer on the anode (or on the hole injection layer, if present).

[0037] The hole transport layer is a layer that receives holes from the positive electrode or the hole injection layer and transports them to the light emitting layer. As a hole transport material, a material that can receive holes from the positive electrode or the hole injection layer and move them to the light emitting layer and has high mobility for holes is suitable.

[0038] Specific examples of the hole transport material include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0039] Meanwhile, the hole transport layer may be composed of two or more materials, and each material may be mixed to form one layer or may be composed of separate layers. When composed of separate layers, they may be distinguished by expressions such as "first" and "second", which may be understood to be merely for the purpose of distinction.

[0040] Electron Blocking Layer The organic light emitting device according to the present invention may optionally include an electron blocking layer on the hole transport layer.

[0041] The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the anode from passing to the hole transport layer without being recombined in the light emitting layer, and is also called an electron blocking layer or an electron inhibiting layer. The electron blocking layer is preferably made of a material having a smaller electron affinity than the electron transport layer.

[0042] Emitting layer The light-emitting layer used in the present invention means a layer capable of emitting light in the visible light region by combining holes and electrons transferred from the positive electrode and the negative electrode. In general, the light-emitting layer includes a host material and a dopant material, and in the present invention, the compound represented by the above Chemical Formula 1 and the compound represented by the above Chemical Formula 2 are included as hosts.

[0043] Preferably, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-20 aryl; or C containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S 2-20 It is heteroaryl.

[0044] More preferably, Ar1 and Ar2 may each independently be phenyl, biphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenylcarbazolyl, wherein Ar1 and Ar2 may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0045] Most preferably, Ar1 and Ar2 are each independently any one selected from the group consisting of: [ka]

[0046] Preferably, at least one of Ar1 and Ar2 is a substituted or unsubstituted C 6-20 It is aryl.

[0047] More preferably, at least one of Ar1 and Ar2 is phenyl or phenyl substituted with five deuteriums.

[0048] Preferably, Ar1 and Ar2 are all substituted or unsubstituted C 6-20 It is aryl.

[0049] Preferably, Ar1 and Ar2 are each independently phenyl or biphenylyl.

[0050] Preferably, Ar3 is a substituted or unsubstituted C 6-20 It is aryl.

[0051] More preferably, Ar3 is phenyl or biphenylyl, said Ar3 being unsubstituted or substituted with one or more deuterium atoms.

[0052] Most preferably, Ar3 is any one selected from the group consisting of: [ka]

[0053] Preferably, L is a single bond.

[0054] Preferably, R3 is hydrogen, deuterium, or a substituted or unsubstituted C 6-20 It is aryl.

[0055] More preferably, R3 is hydrogen, deuterium, phenyl, or phenyl substituted with five deuteriums.

[0056] Most preferably, R3 is phenyl substituted with 5 deuteriums.

[0057] Preferably, at least one of R2 and R3 is deuterium, and the rest are hydrogen, deuterium, phenyl, or phenyl substituted with 1 to 5 deuterium.

[0058] Preferably, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: [ka]

[0059] [ka]

[0060] In the above Chemical Formula 1-1 to Chemical Formula 1-4, Ar1 to Ar3, L, R1 and R2 are as defined in Chemical Formula 1; R3 may be a phenyl that is unsubstituted or substituted with 1 to 5 deuteriums.

[0061] Representative examples of the compound represented by Formula 1 are as follows:

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] The compound represented by Chemical Formula 1 can be prepared, for example, by the method shown in Reaction Scheme 1 below, and the remaining compounds can be prepared in a similar manner.

[0067] [Reaction Scheme 1] [ka]

[0068] In the reaction formula 1, Ar1 to Ar3, L, R1 to R3, a and b are as defined in the chemical formula 1, and X1 is a halogen, and preferably, X1 is fluorine, chloro or bromo.

[0069] The reaction scheme 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group for the amine substitution reaction can be changed as known in the art. The preparation method is more specifically described in the preparation examples described below.

[0070] Preferably, Ar4 and Ar5 are each independently substituted or unsubstituted C 6-20 aryl; or C containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S 2-20 It is heteroaryl.

[0071] More preferably, Ar4 and Ar5 are each independently biphenylyl, terphenylyl, dibenzofuranyl, dibenzofuranylphenyl, dibenzothiophenyl, or phenylcarbazolyl, wherein Ar4 and Ar5 can be unsubstituted or substituted with one or more deuterium atoms.

[0072] More preferably, Ar4 and Ar5 are each independently any one selected from the group consisting of: [ka]

[0073] More preferably, Ar4 and Ar5 are biphenylyl each substituted with 9 deuterium atoms.

[0074] Preferably, at least one of Ar4 and Ar5 is a substituted or unsubstituted C 6-60 It is aryl.

[0075] More preferably, at least one of Ar4 and Ar5 is a substituted or unsubstituted C 6-20 It is aryl.

[0076] More preferably, at least one of Ar4 and Ar5 is any one selected from the group consisting of: [ka]

[0077] Preferably, R4 to R6 are deuterium, and c+d+e is an integer of 6-10.

[0078] More preferably, R4 to R6 are deuterium and c+d+e is an integer of 8-10.

[0079] Representative examples of the compound represented by Formula 2 are as follows:

[0080] [ka]

[0081] [ka]

[0082] [ka]

[0083] [ka]

[0084] [ka]

[0085] [ka]

[0086] [ka]

[0087] The compound represented by Chemical Formula 2 can be prepared, for example, by the method shown in Reaction Scheme 2 below, and the remaining compounds can be prepared in a similar manner.

[0088] [Reaction Scheme 2] [ka]

[0089] In the reaction formula 2, Ar4 and Ar5 are as defined in the chemical formula 2, and X2 is a halogen, and preferably X2 is fluorine, chlorine, or bromo.

[0090] The reaction scheme 2 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group for the amine substitution reaction can be changed as known in the art. The preparation method is more specifically described in the preparation examples described below.

[0091] Preferably, the weight ratio of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 in the light-emitting layer is 10:90 to 90:10, more preferably 20:80 to 80:20, 30:70 to 70:30, or 40:60 to 60:40.

[0092] Meanwhile, the light-emitting layer may further include a dopant in addition to the host. The dopant material is not particularly limited as long as it is a material used in an organic light-emitting device. For example, aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. are included. Specifically, aromatic amine derivatives include fused aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periflanthene, which have arylamino groups, and styrylamine compounds include substituted or unsubstituted arylamines substituted with at least one arylvinyl group, in which one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups are substituted or unsubstituted. Specifically, styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc. are included, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0093] Hole Blocking Layer The organic light-emitting device according to the present invention may optionally include an electron transport layer on the light-emitting layer.

[0094] The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the positive electrode from being recombined in the light emitting layer and passing to the electron transport layer, and is also called a hole suppression layer or a hole blocking layer. For the hole blocking layer, a material with a large ionization energy is preferable.

[0095] electron transport layer The organic light-emitting device according to the present invention may optionally include an electron transport layer on the light-emitting layer.

[0096] The electron transport layer receives electrons from the anode or the electron injection layer formed on the anode, transports the electrons to the light-emitting layer, and suppresses the transport of holes in the light-emitting layer. As the electron transport material, a material that can efficiently receive electrons from the anode and transport them to the light-emitting layer and has high mobility for electrons is suitable.

[0097] Specific examples of the electron transport material include, but are not limited to, Al complex of 8-hydroxyquinoline; complex containing Alq3; organic radical compound; hydroxyflavone-metal complex. The electron transport layer can be used with any desired cathode material as used according to conventional techniques. In particular, examples of suitable cathode materials are conventional materials with low work functions followed by an aluminum or silver layer. In particular, cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum or silver layer.

[0098] electron injection layer The organic light-emitting device according to the present invention may further include an electron injection layer on the light-emitting layer (or on the electron transport layer, if present) as required.

[0099] The electron injection layer is a layer that injects electrons from an electrode, and it is preferable to use a compound that has the ability to transport electrons, has an excellent electron injection effect from the negative electrode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and has excellent thin-film forming ability.

[0100] Specific examples of materials that can be used in the electron injection layer include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, pre-olenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0101] Examples of the metal complex compound include, but are not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtholato)gallium.

[0102] Meanwhile, in the present invention, the "electron injection and transport layer" refers to a layer that serves both the functions of the electron injection layer and the electron transport layer, and a material that serves the functions of each layer may be used alone or in combination, but is not limited thereto.

[0103] Organic light-emitting device The structure of an organic light-emitting device according to the present invention is illustrated in Figures 1 and 2. Figure 1 illustrates an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. Figure 2 illustrates an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a first hole transport layer 6, a second hole transport layer 7, an electron blocking layer 8, a light-emitting layer 3, a hole blocking layer 9, an electron injection and transport layer 10, and a negative electrode 4.

[0104] The organic light emitting device according to the present invention may be manufactured by sequentially stacking the above-mentioned components. In this case, a metal or conductive metal oxide or alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a positive electrode, and the above-mentioned layers may be formed thereon, and then a material that can be used as a negative electrode may be deposited thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a negative electrode material on a substrate in the reverse order of the above-mentioned components, followed by a positive electrode material (WO2003 / 012890). In addition, the light emitting layer may be formed by a solution coating method as well as a vacuum deposition method of a host and a dopant. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like.

[0105] Meanwhile, the organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided emission device, and may be a bottom emission device which requires relatively high luminous efficiency.

[0106] Hereinafter, preferred examples will be presented for the understanding of the present invention. However, the following examples are provided for the purpose of making the present invention more easily understandable, and are not intended to limit the scope of the present invention.

[0107] [Production Example] Preparation Example 1: Preparation of Compound 1-1

[0108] (Production Example 1-1) Production of Compound 1-1(a) [ka]

[0109] Under a nitrogen atmosphere, 4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7 (30g, 118.5mmol) and (phenyl-d5)boronic acid (15g, 118.5mmol) were added to 600ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (49.1g, 355.5mmol) was dissolved in 49ml of water and added, and after thorough stirring, tetrakistriphenyl-phosphinopalladium (4.1g, 3.6mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1513mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a white solid compound 1-1(a) (19.4 g, 64%, MS: [M+H] + =256.4).

[0110] (Production Example 1-2) Production of Compound 1-1 [ka]

[0111] Under a nitrogen atmosphere, 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine (20g, 47.6mmol) and 1-1(a) (12.2g, 47.6mmol) were added to 200ml of xylene and stirred and refluxed. Sodium tertiary butoxide (5.8g, 60.5mmol) was then added, and after thorough stirring, bis(tritertiary butyl phosphine)palladium (0.3g, 0.6mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 380mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain yellow solid compound 1-1 (18.3g, 60%, MS: [M+H] + =639.8) was produced.

[0112] Preparation Example 2: Preparation of Compound 1-2

[0113] (Production Example 2-1) Production of Compound 1-2(a) [ka]

[0114] A white solid compound 1-12(b) (17.9 g, 59%, MS: [M+H]) was obtained in the same manner as in Preparation 1-1, except that 2-bromo-9H-carbazole-1,2,3,5,6,7,8-d7 was used instead of 4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7. + =256.4).

[0115] (Production Example 2-2) Production of Compound 1-2 [ka]

[0116] A yellow solid, Compound 1-2 (19.2 g, 63%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1, except that Compound 1-2(a) was used instead of Compound 1-1(a). + =639.8) was produced.

[0117] Preparation Example 3: Preparation of Compound 1-3

[0118] (Production Example 3-1) Production of Compound 1-3(a) [ka]

[0119] A white solid compound 1-12(b) (21.5 g, 71%, MS: [M+H]) was obtained in the same manner as in Preparation 1-1, except that 3-bromo-9H-carbazole-1,2,3,5,6,7,8-d7 was used instead of 4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7. + =256.4).

[0120] [ka]

[0121] (Production Example 3-2) Production of Compound 1-3(b) Under a nitrogen atmosphere, 2(-3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine (30 g, 82.9 mmol) and (phenyl-d5)boronic acid (10.5 g, 82.9 mmol) were added to 600 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (34.4 g, 248.8 mmol) was dissolved in 34 ml of water and added, and the mixture was thoroughly stirred, after which tetrakistriphenyl-phosphinopalladium (2.9 g, 2.5 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1700 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound 1-3(b) (24 g, 71%, MS: [M+H] + =409.5).

[0122] (Production Example 3-3) Production of Compound 1-3 A yellow solid compound 1-3 (15.8 g, 50%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-2, except that compound 1-3(b) was used instead of 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine and compound 1-3(a) was used instead of compound 1-1(a). + =644.9) was produced.

[0123] Preparation Example 4: Preparation of Compound 1-4

[0124] (Production Example 4-1) Production of Compound 1-4(a) [ka]

[0125] A white solid compound 1-12(b) (20.0 g, 66%, MS: [M+H]) was obtained in the same manner as in Preparation 1-1, except that 1-bromo-9H-carbazole-1,2,3,5,6,7,8-d7 was used instead of 4-bromo-9H-carbazole-1,2,3,5,6,7,8-d7. + =256.4).

[0126] (Production Example 4-2) Production of Compound 1-4 [ka]

[0127] A yellow solid compound 1-4 (19.3 g, 67%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-2, except that 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine and compound 1-4(a) was used instead of compound 1-1(a). + =715.9) was produced.

[0128] Preparation Example 5: Preparation of Compound 1-5 [ka]

[0129] A yellow solid compound 1-5 (14.3 g, 50%, MS: [M+H]) was obtained in the same manner as in Preparation 1, except that 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine. + =729.9).

[0130] Preparation Example 6: Preparation of Compound 1-6 [ka]

[0131] A yellow solid compound 1-6 (14.3 g, 50%, MS: [M+H]) was obtained in the same manner as in Preparation 2, except that 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-2-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine. + =729.9).

[0132] Preparation Example 7: Preparation of Compound 1-7 [ka]

[0133] (Preparation Example 7-1) Preparation of Compound 1-7(a) A white solid compound 1-7(a) (13.2 g, 60%, MS: [M+H]) was obtained in the same manner as in Preparation 3-2, except that 2-(3-chloro-4-fluorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine.+ =499.6) was produced.

[0134] (Production Example 7-2) Production of Compound 1-7 A yellow solid, Compound 1-7 (24 g, 76%, MS: [M+H]) was obtained in the same manner as in Preparation Example 3-3, except that Compound 1-7(a) was used instead of Compound 1-3(b). + =644.9) was produced.

[0135] Preparation Example 8: Preparation of Compound 1-8 [ka]

[0136] A yellow solid compound 1-8 (20.4 g, 69%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-2, except that 2-(dibenzo[b,d]furan-4-yl)-4-(6-fluoro-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine was used instead of 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine and compound 1-3(a) was used instead of compound 1-1(a). + =729.9).

[0137] Preparation Example 9: Preparation of Compound 1-9 [ka]

[0138] The yellow solid compound 1-9 (20.3 g, 74%, MS: [M+H]) was obtained in the same manner as in Preparation 4-2, except that 3-(4-(6-chloro-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole was used instead of 2-([1,1'-biphenyl]-4-yl)-4-(6-chloro-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine.+ =805) was manufactured.

[0139] Preparation Example 10: Preparation of Compound 1-10 [ka]

[0140] (Preparation Example 10-1) Preparation of Compound 1-10(a) Under a nitrogen atmosphere, 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (30 g, 108 mmol) and (3-chloro-4-fluorophenyl)boronic acid (18.8 g, 108 mmol) were added to 600 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (44.8 g, 324 mmol) was dissolved in 45 ml of water and added, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (3.7 g, 3.2 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 2008 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain a white solid compound 1-10(a) (22.5 g, 56%, MS: [M+H] + =372.9) was produced.

[0141] (Preparation Example 10-2) Preparation of Compound 1-10(b) A white solid compound 1-10(b) (13.2 g, 60%, MS: [M+H]) was obtained in the same manner as in Preparation Example 3-2, except that compound 1-10(a) was used instead of 2-(3-chloro-4-fluorophenyl)-4,6-diphenyl-1,3,5-triazine and [1,1'-biphenyl]-3-ylboronic acid was used instead of (phenyl-d5)boronic acid. + =499.6) was produced.

[0142] (Production Example 10-3) Production of Compound 1-10 A yellow solid compound 1-10 (24.9 g, 56%, MS: [M+H]) was obtained in the same manner as in Preparation Example 1-2, except that compound 1-10(b) was used instead of 2-(6-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine and compound 1-3(a) was used instead of compound 1-1(a). + =726) was manufactured.

[0143] Preparation Example 11: Preparation of Compound 2-1 [ka]

[0144] Under a nitrogen atmosphere, 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole (10g, 24.5mmol) and 4-bromo-1,1'-biphenyl (5.7g, 24.5mmol) were added to 200ml of xylene and stirred and refluxed. Sodium tertiary butoxide (7.1g, 73.4mmol) was then added and thoroughly stirred, followed by bis(tri-tertiary butyl phosphine)palladium (0.4g, 0.7mmol). After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 412mL of chloroform and washed twice with water, after which the organic layer was separated, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to give a white solid compound 2-1 (8.6 g, 63%, MS: [M+H] + =561.7) was produced.

[0145] Preparation Example 12: Preparation of Compound 2-2 [ka]

[0146] A white solid compound 2-2 (6.6 g, 48%, MS: [M+H]) was obtained in the same manner as in Preparation 13, except that 3-bromo-1,1'-biphenyl was used instead of 4-bromo-1,1'-biphenyl. + =561.7) was produced.

[0147] Preparation Example 13: Preparation of Compound 2-3 [ka]

[0148] A white solid compound 2-3 (7.5 g, 55%, MS: [M+H]) was obtained in the same manner as in Preparation 13, except that 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole was used instead of 4-bromo-1,1'-biphenyl, and 3-bromo-1,1'-biphenyl was used instead of 4-bromo-1,1'-biphenyl. + =561.7) was produced.

[0149] Preparation Example 14: Preparation of Compound 2-4 [ka]

[0150] A white solid compound 2-4 (8.6 g, 61%, MS: [M+H]) was obtained in the same manner as in Preparation 13, except that 1-bromodibenzo[b,d]furan was used instead of 4-bromo-1,1'-biphenyl. + =575.7).

[0151] Preparation Example 15: Preparation of Compound 2-5 [ka]

[0152] A white solid compound 2-5 (5.8 g, 41%, MS: [M+H]) was obtained in the same manner as in Preparation 13, except that 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole was used instead of 4-bromo-1,1'-biphenyl, and 2-bromodibenzo[b,d]furan was used instead of 4-bromo-1,1'-biphenyl. + =575.7).

[0153] Preparation Example 16: Preparation of Compound 2-6 [ka]

[0154] (Preparation Example 16-1) Preparation of Compound 2-6(a) Under a nitrogen atmosphere, 5,8-dihydroindolo[2,3-c]carbazole (50 g, 195.1 mmol) and TfOH (10 ml) were added to C6D6 (500 ml) and stirred at 40°C for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, D2O (100 ml) was added, and the mixture was stirred for 30 minutes, after which trimethylamine (12 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform. The extract was dried over MgSO4 and recrystallized from ethanol to obtain 30.9 g of compound 2-6(a). (Yield 60%, MS: [M+H] + =265)

[0155] (Production Example 16-2) Production of Compound 2-6 Under a nitrogen atmosphere, compound 2-6(a) (10 g, 37.8 mmol) and 4-bromo-1,1'-biphenyl (17.6 g, 75.6 mmol) were added to 200 ml of xylene and stirred and refluxed. Sodium tertiary butoxide (21.8 g, 227.0 mmol) was then added and thoroughly stirred, after which bis(tri-tertiary butyl phosphine)palladium (2 g, 3.8 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 645 mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain white solid compound 2-6 (17.2 g, 80%, MS: [M+H] + =569.8).

[0156] Preparation Example 17: Preparation of Compound 2-7 [ka]

[0157] Compound 2-1 (10 g, 17.8 mmol) and TfOH (2 ml) were added to C6D6 (100 ml) under a nitrogen atmosphere and stirred at 40°C for 4 hours. After the reaction was completed, the temperature was lowered to room temperature, D2O (20 ml) was added, and the mixture was stirred for 30 minutes, after which trimethylamine (2.4 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and chloroform, and then anhydrous magnesium sulfate was added and stirred, and the mixture was filtered and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to obtain white solid compound 2-7 (7.9 g, 76%, MS: [M+H] + =587) was produced.

[0158] Preparation Example 18: Preparation of Compound 2-8 [ka]

[0159] A white solid, compound 2-8 (7.4 g, 71%, MS: [M+H]) was obtained in the same manner as in Preparation Example 17, except that compound 2-2 was used instead of compound 2-1. + =587) was produced. EXAMPLES

[0160] Example 1 A glass substrate coated with a 100 nm-thick thin film of ITO (indium tin oxide) was placed in distilled water with detergent dissolved therein and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a filter manufactured by Millipore Co. The ITO was cleaned for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was also cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition machine.

[0161] On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 60 nm to form a hole injection layer. The following compound HAT was vacuum deposited on the hole injection layer to form a first hole transport layer with a thickness of 5 nm, and the following compound HT-A was vacuum deposited on the first hole transport layer to form a second hole transport layer with a thickness of 50 nm. The following compound HT-B was thermally vacuum deposited to a thickness of 45 nm on the hole transport layer to form an electron blocking layer. On the electron blocking layer, the previously prepared compound 1-1 was mixed with the following compound 2-1 in a weight ratio of 1:1, and then the following compound GD was vacuum deposited with a weight ratio of 95:5 (mixture of compounds 1-1 and 2-1: compound GD) to a thickness of 40 nm to form a light emitting layer. On the light emitting layer, the following compound ET-A was vacuum deposited to a thickness of 5 nm to form a hole blocking layer. On the hole blocking layer, the following compound ET-B and the following compound LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injecting and transporting layer having a thickness of 35 nm.

[0162] Lithium fluoride (LiF) was deposited on the electron injection and transport layer to a thickness of 1 nm, and then aluminum was deposited to a thickness of 100 nm to form a negative electrode, thereby preparing an organic light emitting device.

[0163] [ka]

[0164] During the above process, the deposition rate of the organic material was maintained at 0.04 nm / sec to 0.09 nm / sec, the deposition rate of lithium fluoride was maintained at 0.03 nm / sec, and the deposition rate of aluminum was maintained at 0.2 nm / sec. The degree of vacuum during deposition was 1×10 -7 torr~5×10 -5 torr was maintained.

[0165] Examples 2 to 40 and Comparative Examples 1 to 23 An organic light-emitting device was manufactured in the same manner as in Example 1, except that a compound shown in Table 1 or Table 2 below was used instead of compound 1-1, and a compound shown in Table 1 or Table 2 below was used instead of compound 2-1. In Table 2 below, the structures of compounds 3-1 to 3-5, 4-1 and 4-2 are as follows, respectively.

[0166] [ka]

[0167] [Experimental Example] A current was applied to the organic light emitting devices fabricated in Examples 1 to 40 and Comparative Examples 1 to 23 to measure the voltage, efficiency, luminous color, and lifespan (T95). The results are shown in Tables 1 and 2. At this time, the voltage and efficiency were 10 mA / cm 2 The current density of T95 was 20mA / cm. 2 means the time (hr) it takes for the initial brightness to decrease to 95%.

[0168] [Table 1]

[0169] [Table 2]

[0170] The compound of the present invention, represented by Chemical Formula 1, is designed to have a twisted structure between the triazine moiety and the carbazole moiety by introducing a substituted / unsubstituted aryl group into the Ar3 position, which causes steric hindrance. This molecular structure allows the electron donating property of the carbazole substituent to act, increasing the stability of the whole molecule, and the electron distribution is separated, resulting in additional charge transfer (CT) properties, which leads to improved voltage, efficiency, and life characteristics.

[0171] It was confirmed that compound 3-1, among the comparative compounds, could not form a twisted structure due to the absence of a substituent corresponding to the Ar3 position of the present invention, causing a decrease in characteristics, and that in the case of compounds 3-2 to 3-4, a dibenzofuran or dibenzothiophene substituent exhibiting strong electronic characteristics was introduced into the carbazole substituent or phenyl linker, and the occurrence of charge transfer characteristics was suppressed by offsetting the electron donating characteristics of the carbazole substituent. It was confirmed that compound 3-5 showed a much larger decrease in lifespan when not deuterium-substituted compared to the deuterium-substituted carbazole, because deuterium was not substituted into the carbazole unit, resulting in a lack of twist in structure compared to the deuterium-substituted carbazole, and a large decrease in stability. It was confirmed that compound 3-5 showed a much larger decrease in lifespan when not deuterium-substituted compared to the general deuterium-substituted / non-substituted effect.

[0172] The compound represented by Chemical Formula 2 of the present invention is based on an indolocarbazole-based core exhibiting strong hole injection properties, and when used together with Chemical Formula 1 exhibiting strong electron injection properties, it has been confirmed that the compound exhibits excellent effects in improving device efficiency and voltage by rapidly injecting electrons and holes.

[0173] On the other hand, when Compound 4-1 or 4-2 was used, the hole injection characteristics were deteriorated, leading to a loss of the overall electron / hole balance in the device, resulting in a deterioration in characteristics. [Explanation of symbols]

[0174] 1: Substrate 2: Positive electrode 3: Light-emitting layer 4: Negative electrode 5: Hole injection layer 6: First hole transport layer 7: Second hole transport layer 8: Electron blocking layer 9: Hole blocking layer 10: Electron injection and transport layer

Claims

1. a positive electrode; a light-emitting layer; and a negative electrode, The light-emitting layer includes a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: Organic light-emitting devices: 【Chemistry 1】 In the above Chemical Formula 1, Ar １ and Ar ２ each independently represents a substituted or unsubstituted C ６－６０ aryl; or C containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S ２－６０ is heteroaryl, Ar ３ is a substituted or unsubstituted C ６－６０ is aryl, L is a single bond; ６－６０ arylene; or C containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S. ２－６０ Heteroarylene, R １ and R ２ are each independently hydrogen or deuterium; R ３ is hydrogen, deuterium, or substituted or unsubstituted C ６－６０ is aryl, R ２ and R ３ At least one of the is deuterium, a is an integer from 0 to 3; b is an integer equal to 7; 【Chemistry 2】 In the above Chemical Formula 2, Ar ４ and Ar ５ each independently represents a substituted or unsubstituted C ６－６０ aryl; or C containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S ２－６０ is heteroaryl, R ４ ~R ６ are each independently hydrogen or deuterium; c and e are integers from 0 to 4; d is an integer from 0 to 2.

2. Ar １ and Ar ２ are each independently phenyl, biphenylyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, or phenylcarbazolyl; The Ar １ and Ar ２ are each independently unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

3. Ar １ and Ar ２ is independently any one selected from the group consisting of: The organic light-emitting device according to claim 1 : 【Chemistry 3】

4. Ar １ and Ar ２ at least one of is phenyl or phenyl substituted with five deuteriums; 10. The organic light-emitting device of claim 1 .

5. Ar ３ is phenyl or biphenylyl, The Ar ３ is unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

6. Ar ３ is any one selected from the group consisting of the following: The organic light-emitting device according to claim 1 : 【Chemistry 4】

7. L is a single bond; The organic light-emitting device according to claim 1 .

8. R ３ is hydrogen, deuterium, phenyl, or phenyl substituted with five deuteriums; The organic light-emitting device according to claim 1 .

9. R ２ and R ３ at least one of is deuterium, and the rest are hydrogen, deuterium, phenyl, or phenyl substituted with 1 to 5 deuteriums; The organic light-emitting device according to claim 1 .

10. The compound represented by the formula 1 is any one selected from the group consisting of: The organic light-emitting device according to claim 1 : 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】

11. Ar ４ and Ar ５ are each independently biphenylyl, terphenylyl, dibenzofuranyl, dibenzofuranylphenyl, dibenzothiophenyl, or phenylcarbazolyl; The Ar ４ and Ar ５ is unsubstituted or substituted with one or more deuterium atoms; The organic light-emitting device according to claim 1 .

12. Ar ４ and Ar ５ is independently any one selected from the group consisting of: The organic light-emitting device according to claim 1 : 【Chemistry 9】

13. Ar ４ and Ar ５ At least one of the following is a substituted or unsubstituted C ６－６０ is aryl, The organic light-emitting device according to claim 1 .

14. Ar ４ and Ar ５ At least one of the above is any one selected from the group consisting of the following: The organic light-emitting device according to claim 1 : 【Chemistry 10】

15. The compound represented by the formula 2 is any one selected from the group consisting of: The organic light-emitting device according to claim 1 : 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】

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