Organic light-emitting device

Abstract

To provide an organic light-emitting element with improved drive voltage, efficiency and lifetime.SOLUTION: An organic light-emitting element includes a positive electrode, a negative electrode, and a light emitting layer between the positive electrode and the negative electrode, and the light emitting layer includes a first compound represented by the following chemical formula and a second compound represented by a specific chemical formula.SELECTED DRAWING: None

Description

[Technical field]

[0001] [CROSS REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0170947 filed on December 19, 2019, and Korean Patent Application No. 10-2020-0167777 filed on December 3, 2020, 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] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. Organic light emitting devices using the 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, and therefore many researches are being conducted on these devices.

[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 from the positive electrode and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons come into contact with each other, excitons are formed, and when the excitons fall to their bottom state, light is emitted.

[0005] In such organic light-emitting devices, there is a continuing demand for the development of organic light-emitting devices with improved driving voltage, efficiency, and life span. Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention provides an organic light emitting device with improved driving voltage, efficiency and lifetime. [Means for solving the problem]

[0007] The present invention provides an organic light-emitting device comprising: A positive electrode, a negative electrode, and a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer includes a first compound represented by the following Chemical Formula 1 and a second compound represented by the following Chemical Formula 2, [Chemical formula 1] [ka] In the above Chemical Formula 1, A is a benzene ring fused to two adjacent 5-membered rings, Ar 1 ~Ar 3 each independently represents a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; R 1 each independently represents hydrogen; deuterium; halogen; cyano; a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; x is an integer from 1 to 10; However, the above Ar 1 ~Ar 3 , and R 1 At least one of R is substituted with one or more deuterium atoms, or 1 is deuterium, and said first compound is substituted with at least five deuterium atoms; [Chemical formula 2] [ka] In the above Chemical Formula 2, B is a benzene ring fused to two adjacent 5-membered rings, Ar 4 is a substituted or unsubstituted aryl having 6 to 60 carbon atoms, Ar 5 is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms and containing one heteroatom selected from the group consisting of N, O, and S; R 2 each independently represents hydrogen; deuterium; halogen; cyano; a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; and y is an integer from 1 to 10. Effect of the Invention

[0008] The organic light emitting device described above has excellent driving voltage, efficiency and life span by including the first compound represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 in the light emitting layer. [Brief description of the drawings]

[0009] [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 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a negative electrode 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The present invention will now be described in more detail to aid in its understanding.

[0011] In this specification, [ka] or [ka] denotes a bond that is connected to another substituent.

[0012] 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 a substituent in which two or more of the above-mentioned exemplified substituents are linked. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are linked.

[0013] In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but the carbon number is preferably 1 to 40. Specifically, the carbonyl group may have the following structure, but is not limited thereto. [ka]

[0014] 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 ester group may be a group having the following structural formula, but is not limited thereto. [ka]

[0015] In this specification, the number of carbon atoms of the imido group is not particularly limited, but is preferably 1 to 25. Specifically, it may be a group having the following structure, but is not limited thereto. [ka]

[0016] 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.

[0017] 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.

[0018] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0019] 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 alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. 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.

[0020] 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 another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to 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 thereto.

[0021] 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 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, but are not limited thereto.

[0022] 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.

[0023] In this specification, the fluorenyl group may be substituted, and two of the substituents may be bonded together to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to these.

[0024] In this specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a hetero element, 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, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl groups.

[0025] In this specification, the above-mentioned explanation regarding the aryl group is applicable to the aralkyl group, the aralkenyl group, the alkylaryl group, and the aryl group in the arylamine group. In this specification, the above-mentioned explanation regarding the alkyl group is applicable to the aralkyl group, the alkylaryl group, and the alkylamine group. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heteroaryl in the heteroarylamine. In this specification, the above-mentioned explanation regarding the alkenyl group is applicable to the alkenyl group in the aralkenyl group. In this specification, the above-mentioned explanation regarding the aryl group is applicable to the arylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heteroarylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the aryl group or the cycloalkyl group is applicable to the hydrocarbon ring, except that it is not a monovalent group but is formed by bonding two substituents. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heterocyclic group, except that it is not a monovalent group but is formed by bonding two substituents.

[0026] The organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, an emission layer, and an anode are sequentially stacked on a substrate, or an inverted type in which an anode, an emission layer, and an anode are sequentially stacked on a substrate. The organic light emitting device may further selectively include at least one layer selected from a hole injection layer, a hole transport layer, and an electron inhibiting layer between the anode and the emission layer, and may further include at least one layer selected from a hole blocking layer, an electron injection layer, and an electron transport layer between the anode and the emission layer. The electron injection layer and the electron transport layer may also be included in the form of a single layer of electron injection and transport layers, rather than being individual layers.

[0027] The present invention will be described in detail below for each component.

[0028] 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.

[0029] The positive electrode 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 positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SNO 2 Examples of the conductive polymers include, but are not limited to: a combination of a metal such as Sb with an oxide; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0030] The negative electrode material is preferably a material with a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF / Al or LiO 2 / Al and other multi-layered materials, but are not limited to these.

[0031] Hole injection layer The organic light emitting device according to the present invention may further include a hole injection layer on the positive electrode, if necessary.

[0032] 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 from 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.

[0033] Specific examples of hole injection materials 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.

[0034] Hole transport layer The organic light-emitting device according to the present invention optionally comprises a hole transport layer on the anode (or on the hole injection layer, if present).

[0035] The hole transport layer is a layer that receives holes from the positive electrode or the hole injection layer and transports the holes to the light emitting layer. As the 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 preferable.

[0036] 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.

[0037] 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 contains a host material and a dopant material, and in the present invention, the first compound represented by the above Chemical Formula 1 and the second compound represented by the above Chemical Formula 2 are contained as hosts.

[0038] Preferably, the first compound represented by the formula 1 may be substituted with 5 or more deuterium atoms. 1 ~Ar 3 , and R 1 At least one of R is substituted with one or more deuterium atoms, or1 by substituting at least one of the following with deuterium, such that the first compound can contain 5 or more, or 6 or more, or 7 or more, or 8 or more, or 10 or more deuterium in the compound, or the first compound can be fully substituted with deuterium.

[0039] Preferably, the formula 1 is represented by any one selected from the group consisting of the following formulas 1-1 to 1-6: [Chemical formula 1-1] [ka] [Chemical formula 1-2] [ka] [Chemical formula 1-3] [ka] [Chemical formula 1-4] [ka] [Chemical formula 1-5] [ka] [Chemical formula 1-6] [ka] In the above Chemical Formula 1-1 to Chemical Formula 1-6, Ar 1 ~Ar 3 , R 1 and x is as defined above.

[0040] In the above formula 1, preferably, Ar 1 ~Ar 3 may each independently be phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl.

[0041] In the above formula 1, more preferably, Ar 1 ~Ar 3 is phenyl, and the remaining can each independently be phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl.

[0042] In addition, the Ar 1 ~Ar 3 At least one of the Ar 1 ~Ar 3 At least one of the following structures is selected from the group consisting of: [ka] In the above formula, a is an integer of 1 to 5, b is an integer between 0 and 4, and c is an integer between 0 and 5, provided that b and c are not both 0 at the same time, Each d is independently an integer from 0 to 3, and e is an integer from 0 to 5, provided that d and e are not both 0 at the same time; f is an integer from 0 to 3, and each g is independently an integer from 0 to 5, provided that f and g are not both 0 at the same time; h is an integer between 0 and 3, and i is an integer between 0 and 4, provided that h and i are not both 0 at the same time; j is an integer of 0 to 3, k is an integer of 0 to 4, and each 1 is independently an integer of 0 to 5, provided that j, k, and 1 are not all 0 at the same time; m is an integer from 0 to 4, and n is an integer from 0 to 4, provided that m and n are not both 0 at the same time; o is an integer of 0 to 3, p is an integer of 0 to 4, and q is an integer of 0 to 5, with the proviso that o, p, and q are not all 0 simultaneously.

[0043] Also preferably, the Ar 1 ~Ar 3At least one of is substituted with five or more deuterium atoms.

[0044] More preferably, in the above Chemical Formula 1, the Ar 1 ~Ar 3 at least one of is phenyl substituted with five deuteriums, and the remainder can be unsubstituted phenyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, unsubstituted fluorenyl, unsubstituted 9,9-dimethylfluorenyl, unsubstituted 9,9-diphenylfluorenyl, unsubstituted carbazol-9-yl, or unsubstituted 9-phenyl-9H-carbazolyl.

[0045] As an example, the Ar 1 ~Ar 3 are all phenyl, provided that the Ar 1 ~Ar 3 At least one of the following, specifically Ar 1 ~Ar 3 Any one, two, or all three of the following are replaced with five deuterium atoms:

[0046] As yet another example, the Ar 1 ~Ar 3 one of is unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, unsubstituted fluorenyl, unsubstituted 9,9-dimethylfluorenyl, unsubstituted 9,9-diphenylfluorenyl, unsubstituted carbazol-9-yl, or unsubstituted 9-phenyl-9H-carbazolyl, and the remainder are phenyl, with the proviso that at least one of the remainders, i.e., one or all two of the remainders, is substituted with five deuteriums.

[0047] Also preferably, the Ar 1 ~Ar 3at least one of is biphenyl substituted with 5 or more deuteriums, terphenyl substituted with 5 or more deuteriums, dibenzofuranyl substituted with 5 or more deuteriums, dibenzothiophenyl substituted with 5 or more deuteriums, fluorenyl substituted with 5 or more deuteriums, 9,9-dimethylfluorenyl substituted with 5 or more deuteriums, 9,9-diphenylfluorenyl substituted with 5 or more deuteriums, carbazol-9-yl substituted with 5 or more deuteriums, or 9-phenyl-9H-carbazolyl substituted with 5 or more deuteriums, and the remainder can each independently be unsubstituted phenyl or unsubstituted biphenyl.

[0048] As an example, the Ar 1 ~Ar 3 One of the groups is a biphenyl substituted with five deuterium atoms, and the remaining groups may be, independently, an unsubstituted phenyl or an unsubstituted biphenyl. In this case, the biphenyl substituted with five deuterium atoms is, for example, represented by the following structure: [ka] In the above formula, r is an integer of 0 to 4, and more specifically, 0.

[0049] As another example, the Ar 1 ~Ar 3 Two of the structures are biphenyls substituted with five deuterium atoms, and the remaining one is an unsubstituted phenyl. In this case, the biphenyl substituted with five deuterium atoms is represented by the structure above.

[0050] As yet another example, the Ar 1 ~Ar 3one of which is fully deuterated biphenyl, fully deuterated terphenyl, fully deuterated dibenzofuranyl, fully deuterated dibenzothiophenyl, fully deuterated fluorenyl, fully deuterated 9,9-dimethylfluorenyl, fully deuterated 9,9-diphenylfluorenyl, fully deuterated carbazol-9-yl, or fully deuterated 9-phenyl-9H-carbazolyl, and the rest are all unsubstituted phenyl.

[0051] Also preferably, the Ar 1 ~Ar 3 are each independently phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl; 1 ~Ar 3 is fully substituted with deuterium.

[0052] In addition, in the above Chemical Formula 1, preferably, 1 In this case, in the formula 1, x is an integer of 10, and Ar 1 ~Ar 3 At least one of the following is substituted with five or more deuterium atoms:

[0053] In addition, in the above Chemical Formula 1, preferably, 1 At least five of the R are deuterium and the rest are hydrogen. In this case, in Formula 1, x is an integer of 10. For example, in Formula 1, 1 Five, six, seven, or eight of the atoms are deuterium and the remainder are hydrogen, or R 1 All ten of the atoms can be deuterium.

[0054] Representative examples of the first compound represented by Formula 1 are as follows: [ka]

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[0055] The first compound represented by Chemical Formula 1 can be prepared, for example, by a method as shown in Reaction Scheme 1 below. [Reaction Scheme 1] [ka] In the above reaction scheme 1, Ar 1 ~Ar 3 , R 1 and x is as defined in Formula 1 above, and X is a halogen, preferably chlorine or bromine.

[0056] 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 according to those known in the art. The preparation method is further exemplified in the preparation examples described below.

[0057] On the other hand, the chemical formula 2 is preferably represented by any one selected from the group consisting of the following chemical formulas 2-1 to 2-6, and more preferably represented by any one selected from the group consisting of the following chemical formulas 2-1 to 2-3: [Chemical formula 2-1] [ka] [Chemical formula 2-2] [ka] [Chemical formula 2-3] [ka] [Chemical formula 2-4] [ka] [Chemical formula 2-5] [ka] [Chemical formula 2-6] [ka] In the above Chemical Formula 2-1 to Chemical Formula 2-6, Ar 4 , Ar 5 , R 2 and y is as defined above.

[0058] In the above formula 2, preferably, Ar 4 and Ar 5 are each independently an unsubstituted aryl having 6 to 30 carbon atoms, and more preferably, Ar 4 and Ar 5 are each independently unsubstituted phenyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted fluorenyl, unsubstituted 9,9-dimethylfluorenyl, or unsubstituted 9,9-diphenylfluorenyl.

[0059] In addition, in the above-mentioned chemical formula 2, preferably, Ar 4 is an unsubstituted aryl having 6 to 30 carbon atoms, and Ar 5 is an unsubstituted heteroaryl having 5 to 60 carbon atoms and containing one heteroatom selected from the group consisting of N, O, and S, and more preferably, Ar 4 is unsubstituted phenyl, unsubstituted biphenyl or unsubstituted terphenyl; Ar 5is unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, unsubstituted carbazol-9-yl, or unsubstituted 9-phenyl-9H-carbazolyl.

[0060] In the above formula 2, preferably, R 2 are all hydrogen, and y is an integer equal to 10.

[0061] Representative examples of the compound represented by Formula 2 are as follows: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0062] The compound represented by Chemical Formula 2 can be prepared, for example, by a method as shown in Reaction Scheme 2 below. [Reaction Scheme 2] [ka] In the above reaction scheme 2, Ar 4 , Ar 5 , R 2 and y is as defined in Formula 2, Y is a halogen, preferably chlorine or bromine. 4 or Ar 5 As defined in.

[0063] 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 according to those known in the art. The preparation method is further exemplified in the preparation examples described below.

[0064] In the above reaction scheme 2, the reaction of compound (III) and compound (IV) is shown in one step. 4 and Ar 5 are different from each other, Ar in compound (IV) is represented by Ar 4 and Ar 5 In this case, the order of the reaction steps is not particularly limited.

[0065] Preferably, in the light-emitting layer, the weight ratio of the first compound represented by Chemical Formula 1 to the second compound represented by Chemical Formula 2 is 10:90 to 90:10, more preferably 20:80 to 80:20, 30:70 to 70:30, 30:70 to 50:50, or 30:70 to 40:60.

[0066] Meanwhile, the light-emitting layer further includes 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. Examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, the dopant materials include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0067] electron transport layer The organic light-emitting device according to the present invention optionally includes an electron transport layer on the light-emitting layer.

[0068] The electron transport layer receives electrons from the negative electrode or the electron injection layer formed on the negative electrode, transports the electrons to the light-emitting layer, and suppresses the transmission of holes in the light-emitting layer. As the electron transport material, a material that can efficiently receive electrons injected from the negative electrode and transfer them to the light-emitting layer and has high mobility for electrons is preferable.

[0069] Specific examples of the electron transport material include Al complexes of 8-hydroxyquinoline; Alq 3The electron transport layer may be used with any desired cathode material, such as those used by the prior art. In particular, examples of suitable cathode materials are conventional materials having low work functions, followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, followed in each case by an aluminum or silver layer.

[0070] electron injection layer The organic light-emitting device according to the present invention may further comprise an electron injection layer on the light-emitting layer (or on the electron transport layer if present), if necessary.

[0071] The electron injection layer is a layer that injects electrons from the electrode, and it is preferable to use a compound that has the ability to transport electrons, has an excellent effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into 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.

[0072] Specific examples of the material used for the electron injection layer include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0073] 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-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.

[0074] Organic light-emitting device The structure of an organic light-emitting device according to the present invention is shown in Figures 1 and 2. Figure 1 is a diagram showing 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 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a negative electrode 4.

[0075] 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, followed by deposition of a material to be used as a negative electrode. 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 to a positive electrode material (WO 2003 / 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.

[0076] Meanwhile, the organic light emitting device according to the present invention may be a front emission type, a rear emission type, or a dual emission type, depending on the materials used.

[0077] In the following, preferred examples are presented to aid in understanding the present invention. However, the following examples are merely provided to facilitate understanding of the present invention, and are not intended to limit the scope of the present invention.

[0078] Synthesis Example 1-1: Synthesis of Compound 1-1 Step 1) Synthesis of intermediate A [ka] In a three-neck flask, add 11,12-dihydroindolo[2,3-a]carbazole (15.0 g, 58.5 mmol), 1-bromobenzene-2,3,4,5,6-d5 (10.4 g, 64.4 mmol), bis(tri-tert-butylphosphine)palladium(0)(Pd(Pt-Bu3 ) 2 After adding 0.6 g (1.2 mmol), sodium tert-butoxide (NaOtBu) (8.4 g, 87.8 mmol), and 500 ml of toluene, the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature and then heated under H 2 O was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was diluted with MgSO 4 The mixture was dried and concentrated, and the sample was purified by silica gel column chromatography to obtain 13.2 g of intermediate A (yield 67%, MS [M+H] + =337).

[0079] Step 2) Synthesis of Compound 1-1 [ka] In a three-neck flask, intermediate A (13.0 g, 38.5 mmol), compound A (14.6 g, 42.4 mmol), bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol), sodium tert-butoxide (5.6 g, 57.8 mmol), and 400 ml of xylene were placed, and the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature and then heated under H 2 O was added, and the reaction mixture was transferred to a separatory funnel for extraction. The extract was diluted with MgSO 4 The mixture was dried and concentrated at 40° C., and the sample was purified by silica gel column chromatography. Compound 1-1 (7.9 g) was obtained by sublimation purification (yield 32%, MS [M+H] + =644).

[0080] Synthesis Example 1-2: Synthesis of Compound 1-2 [ka] In step 1 of Synthesis Example 1-1, 1-bromobenzene-2,3,4,5,6-d5 was replaced with bromobenzene to prepare intermediate B, and in step 2, compound a was replaced with compound b. Compound 1-2 was prepared in the same manner as in the preparation of compound 1-1 (MS [M+H] + =644).

[0081] Synthesis Example 1-3: Synthesis of Compound 1-3 [ka] Compound 1-3 was prepared in the same manner as in the preparation of compound 1-1, except that compound a was replaced with compound c in step 2 of Synthesis Example 1-1 (MS [M+H] + =649)

[0082] Synthesis Example 1-4: Synthesis of Compound 1-4 [ka] In step 1 of Synthesis Example 1-1, 1-bromobenzene-2,3,4,5,6-d5 was replaced with bromo-1,1'-biphenyl to prepare intermediate C, and in step 2, compound a was replaced with compound d to prepare compound 1-4 in the same manner as in the preparation of compound 1-1 (MS [M+H] + =649).

[0083] Synthesis Example 1-5: Synthesis of Compound 1-5 Step 1) Synthesis of intermediate 1-5-1 [ka] In a three-neck flask, intermediate C (15.0 g, 36.7 mmol), compound e (13.9 g, 40.4 mmol), bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol), sodium tert-butoxide (5.3 g, 55.1 mmol), and 400 ml of xylene were placed and stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature and then heated under H 2 O was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was diluted with MgSO 4 The mixture was dried and concentrated at 40° C., and the sample was purified by silica gel column chromatography to obtain 17.1 g of intermediate 1-5-1 (yield 65%, MS [M+H] + =715).

[0084] Step 2) Synthesis of Compounds 1-5 [ka] Compound 1-5-1 (10.0 g, 14.0 mmol), PtO 2 (1.0g, 4.2mmol), D 2 After adding 70 ml of O2, the tube was sealed and heated at 250 °C and 600 psi for 12 hours. When the reaction was complete, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was then diluted with MgSO 4 The mixture was dried and concentrated at 40° C., and the sample was purified by silica gel column chromatography. Then, 4.4 g of compound 1-5 was obtained by sublimation purification (yield 42%, deuterium substitution rate 82%, MS [M+H] + =749).

[0085] Synthesis Example 1-6: Synthesis of Compound 1-6 [ka] Compound 1-6 was prepared in the same manner as in the preparation of compound 1-1, except that in step 2 of Synthesis Example 1-1, intermediate A was replaced with intermediate B and compound a was replaced with compound f (MS [M+H] + =658).

[0086] Synthesis Example 1-7: Synthesis of Compound 1-7 [ka] In step 1 of Synthesis Example 1-1, 1-bromobenzene-2,3,4,5,6-d5 was replaced with 2-bromodibenzo[b,d]furan-1,3,4,6,7,8,9-d7 to prepare intermediate D, and in step 2, compound a was replaced with compound g to prepare compound 1-7 in the same manner as in the preparation of compound 1-1 (MS [M+H] + =660).

[0087] Synthesis Example 1-8: Synthesis of Compound 1-8 [ka] Compound 1-8 was prepared in the same manner as in the preparation of compound 1-1, except that in step 2 of Synthesis Example 1-1, intermediate A was replaced with intermediate B and compound a was replaced with compound h (MS [M+H] + =733).

[0088] Synthesis Example 1-9: Synthesis of Compound 1-9 [ka] Compound 1-9 was prepared in the same manner as compound 1-1, except that 11,12-dihydroindolo[2,3-a]carbazole was replaced with 5,8-dihydroindolo[2,3-c]carbazole in step 1 of Synthesis Example 1-1 (MS [M+H] + =644).

[0089] Synthesis Example 1-10: Synthesis of Compound 1-10 [ka] In step 1 of Synthesis Example 1-1, 11,12-dihydroindolo[2,3-a]carbazole was replaced with 5,7-dihydroindolo[2,3-b]carbazole, and 1-bromobenzene-2,3,4,5,6-d5 was replaced with bromobenzene to prepare intermediate F, and in step 2, compound a was replaced with compound c to prepare compound 1-10 in the same manner as in the preparation of compound 1-1 (MS [M+H] + =644).

[0090] Synthesis Example 1-11: Synthesis of Compound 1-11 [ka] In step 1 of Synthesis Example 1-1, 11,12-dihydroindolo[2,3-a]carbazole was replaced with 5,11-dihydroindolo[3,2-b]carbazole to prepare intermediate G, and in step 2, compound a was replaced with compound i to prepare compound 1-11 in the same manner as in the preparation of compound 1-1 (MS [M+H] + =674)

[0091] Synthesis Example 1-12: Synthesis of Compound 1-12 Step 1) Synthesis of intermediate H [ka] In a three-neck flask, 5,12-dihydroindolo[3,2-a]carbazole (10.0 g, 39.0 mmol), compound j (16.7 g, 42.9 mmol), bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol), sodium tert-butoxide (5.6 g, 58.5 mmol), and toluene (400 mL) were added, and the mixture was stirred under reflux conditions in an argon atmosphere for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and then heated under H 2 O was added, and the reaction mixture was transferred to a separatory funnel for extraction. The extract was diluted with MgSO 4The mixture was dried and concentrated, and the sample was purified by silica gel column chromatography to obtain 16.9 g of intermediate H (yield 71%, MS [M+H] + =608).

[0092] Step 2) Synthesis of Compounds 1-12 [ka] In a three-neck flask, intermediate H (15.0 g, 24.6 mmol), bromobenzene (4.3 g, 27.1 mmol), bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol), sodium tert-butoxide (3.6 g, 37.0 mmol), and 250 ml of xylene were added, and the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature and then degassed with H 2 O was added and the reaction mixture was transferred to a separatory funnel for extraction. The extract was diluted with MgSO 4 The mixture was dried and concentrated at 40° C., and the sample was purified by silica gel column chromatography. Compound 1-12 (5.4 g) was obtained by sublimation purification (yield 32%, MS [M+H] + =684).

[0093] Synthesis Example 1-13: Synthesis of Compound 1-13 [ka] In step 1 of Synthesis Example 1-1, 11,12-dihydroindolo[2,3-a]carbazole was replaced with 5,12-dihydroindolo[3,2-a]carbazole, and 1-bromobenzene-2,3,4,5,6-d5 was replaced with bromobenzene to prepare intermediate I, and in step 2, compound a was replaced with compound k. Compound 1-13 was prepared in the same manner as in the preparation of compound 1-1 (MS [M+H] + =657).

[0094] Synthesis Example 1-14: Synthesis of Compound 1-14 [ka] In step 1 of Synthesis Example 1-1, 11,12-dihydroindolo[2,3-a]carbazole was changed to 11,12-dihydroindolo[2,3-a]carbazole-1,3,5,6,8,10-d6, and 1-bromobenzene-2,3,4,5,6-d5 was changed to 3-bromo-1,1':3',1''-terphenyl to prepare intermediate J, and in step 2, compound a was changed to compound l to prepare compound 1-14 in the same manner as in the preparation of compound 1-1 (MS [M+H] + =723).

[0095] Synthesis Example 1-15: Synthesis of Compound 1-15 [ka] In step 1 of Synthesis Example 1-1, 11,12-dihydroindolo[2,3-a]carbazole was changed to 11,12-dihydroindolo[2,3-a]carbazole-1,2,3,4,5,6,7,8,9,10-d10, and 1-bromobenzene-2,3,4,5,6-d5 was changed to 3-bromo-1,1':3',1''-terphenyl to prepare intermediate K, and in step 2, compound a was changed to compound m to prepare compound 1-15 in the same manner as in the preparation of compound 1-1 (MS [M+H] + =803).

[0096] Synthesis Example 2-1: Synthesis of Compound 2-1 [ka] In a nitrogen atmosphere, 5,8-dihydroindolo[2,3-c]carbazole (15.0 g, 58.5 mmol) and 4-bromo-1,1'-biphenyl (30.0 g, 128.8 mmol) were added to 300 ml of toluene, and the mixture was stirred and refluxed. Then, sodium tert-butoxide (16.9 g, 175.6 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.8 mmol) were added. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated. After stirring with anhydrous magnesium sulfate, the mixture was filtered and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then 9.8 g of compound 2-1 was produced by sublimation purification (yield 30%, MS: [M+H] + =562).

[0097] Synthesis Example 2-2: Synthesis of Compound 2-2 Step 1) Synthesis of intermediate 2-1-1 [ka] In a nitrogen atmosphere, 5,8-dihydroindolo[2,3-c]carbazole (15.0 g, 58.5 mmol) and 4-bromo-1,1':4',1''-terphenyl (19.9 g, 64.4 mmol) were added to 300 ml of toluene, and the mixture was stirred and refluxed. Then, sodium tert-butoxide (8.4 g, 87.8 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.9 g, 1.8 mmol) were added. After reacting for 11 hours, the mixture was cooled to room temperature, and the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved again in chloroform, 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 purified by silica gel column chromatography to produce 19.3 g of intermediate 2-2-1 (yield 68%, MS: [M+H] +=486)

[0098] Step 2) Synthesis of Compound 2-2 [ka] In a nitrogen atmosphere, intermediate 2-2-1 (15.0 g, 31.0 mmol) and 3-bromo-1,1'-biphenyl (7.9 g, 34.0 mmol) were added to toluene 300 ml, and the mixture was stirred and refluxed. Then, sodium tert-butoxide (4.5 g, 46.4 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) were added. After 7 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated using chloroform and water, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then 9.5 g of compound 2-2 was produced by sublimation purification (yield 48%, MS: [M+H] + =638)

[0099] Synthesis Example 2-3: Synthesis of Compound 2-3 [ka] Compound 2-3 was prepared in the same manner as in the preparation of compound 2-2, except that in step 1 of Synthesis Example 2-2, 5,8-dihydroindolo[2,3-c]carbazole was replaced with 5,11-dihydroindolo[3,2-b]carbazole, 4-bromo-1,1':4',1''-terphenyl was replaced with 4-bromo-1,1'-biphenyl, and in step 2, 3-bromo-1,1'-biphenyl was replaced with 4-chloro-1,1':3',1''-terphenyl. (MS [M+H] + =638).

[0100] Synthesis Example 2-4: Synthesis of Compound 2-4 [ka] Compound 2-4 was prepared in the same manner as in the preparation of compound 2-2, except that in step 1 of Synthesis Example 2-2, 5,8-dihydroindolo[2,3-c]carbazole was replaced with 5,12-dihydroindolo[3,2-a]carbazole, 4-bromo-1,1':4',1''-terphenyl was replaced with 2-bromodibenzo[b,d]furan, and in step 2, 3-bromo-1,1'-biphenyl was replaced with 4-bromo-1,1'-biphenyl. (MS[M+H] + =576).

[0101] Example 1 A glass substrate coated with a 1,400 Å-thick thin film of ITO (indium tin oxide) was ultrasonically cleaned in distilled water containing a detergent. 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 made by Millipore Co. The ITO was washed for 30 minutes, and 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 then cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum deposition machine.

[0102] On the ITO transparent electrode thus prepared, the following HT-A and 5 wt% PD were thermally vacuum deposited to a thickness of 100 Å to form a hole injection layer, and then only the HT-A material was deposited to a thickness of 1150 Å to form a hole transport layer. On top of that, the following HT-B was thermally vacuum deposited to a thickness of 450 Å as an electron inhibition layer. Then, Compound 1-1 and Compound 2-1 were vacuum deposited to a thickness of 400 Å as a host for the emitting layer in a weight ratio of 40:60, and 8 wt% GD of the host was vacuum deposited as a dopant to a thickness of 400 Å. Then, the following ET-A was vacuum deposited to a thickness of 50 Å as a hole blocking layer. Then, the following ET-B and Liq were thermally vacuum deposited to a thickness of 250 Å on the hole blocking layer in a ratio of 2:1, and then LiF and magnesium were vacuum deposited to a thickness of 30 Å in a ratio of 1:1 to sequentially form an electron transport layer and an electron injection layer. Magnesium and silver were deposited on the electron injection layer in a ratio of 1:4 to a thickness of 160 Å to form a negative electrode, thereby completing an organic light emitting device. [ka]

[0103] Examples 2 to 23 and Comparative Examples 1 to 20 Organic light emitting devices of Examples 2 to 23 and Comparative Examples 1 to 20 were fabricated in the same manner as in Example 1, except that the host material was changed as shown in any of Tables 1 to 3 below. When a mixture of two compounds was used as the host, the weight ratio between the host compounds is indicated in parentheses. [ka]

[0104] Experimental example: Evaluation of element characteristics A current was applied to the organic light emitting devices fabricated in the Examples and Comparative Examples to measure the voltage, efficiency and lifespan (T95). The results are shown in Tables 1 to 3 below. At this time, the voltage and efficiency were 10 mA / cm 2 The T95 value was measured at a current density of 20 mA / cm. 2 means the time (hr) until the initial brightness decreases to 95%.

[0105] [Table 1]

[0106] [Table 2]

[0107] [Table 3]

[0108] The first compound represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 in the present invention both have an indolocarbazole skeleton. In addition, the first compound contains a triazine group and has a strong ability to transport electrons, and the second compound has a strong ability to transport holes, so that the mixture of the two substances has suitable properties for use as a host. In particular, since the two substances both have an indolocarbazole structure, they are well mixed with each other, which is advantageous for forming an exciplex and is advantageous for effectively transferring energy as a dopant. At this time, the first compound becomes an anion and the second compound becomes a cation to form an exciplex, but the first compound in the anion state becomes more unstable. By replacing five or more deuterium atoms therein, the vibration energy of the first compound becomes lower even in the anion state, and it has more stable energy.

[0109] As a result, as can be seen from Tables 1 and 2, Examples 1 to 23, in which the first compound represented by Chemical Formula 1 and the second compound represented by Chemical Formula 2 of the present invention were both used as the light-emitting layer of the organic light-emitting device, showed significantly improved low voltage, high efficiency, and long life characteristics compared to the comparative example.

Claims

1. A positive electrode, a negative electrode, and a light-emitting layer between the positive electrode and the negative electrode, The light-emitting layer includes a dopant, a first compound represented by the following Chemical Formula 1, and a second compound represented by any one selected from the group consisting of the following Chemical Formulas 2-1, 2-2, and 2-4 to 2-6, [Chemical formula 1] 【Chemistry 1】 In the above Chemical Formula 1, A is a benzene ring fused to two adjacent 5-membered rings, Ar １ ~Ar ３ each independently represents a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 5 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S; R １ each independently represents hydrogen; deuterium; halogen; cyano; a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S; x is an integer from 1 to 10; However, the Ar １ ~Ar ３ , and R １ At least one of R is substituted with one or more deuterium atoms, or １ is deuterium, and said first compound contains at least five deuterium atoms; [Chemical formula 2-1] 【Chemical 34】 [Chemical formula 2-2] 【Chemistry 35】 [Chemical formula 2-4] 【Chemical 37】 [Chemical formula 2-5] 【Chemical Formula 38】 [Chemical formula 2-6] 【Chemical Formula 39】 In the above chemical formulas 2-1, 2-2, and 2-4 to 2-6, Ar ４ is a substituted or unsubstituted aryl having 6 to 60 carbon atoms; Ar ５ is unsubstituted dibenzofuranyl or unsubstituted dibenzothiophenyl, R ２ each independently represents hydrogen; deuterium; halogen; cyano; a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of N, O, and S; and y is an integer from 1 to 10.

2. The organic light-emitting device according to claim 1, wherein the formula 1 is represented by any one selected from the group consisting of the following formulas 1-1 to 1-6: [Chemical formula 1-1] 【Chemistry 3】 [Chemical formula 1-2] 【Chemistry 4】 [Chemical formula 1-3] 【Chemistry 5】 [Chemical formula 1-4] 【Chemistry 6】 [Chemical formula 1-5] 【Chemistry 7】 [Chemical formula 1-6] 【Chemistry 8】 In the above Chemical Formula 1-1 to Chemical Formula 1-6, Ar １ ~Ar ３ , R １ and x is as defined in claim 1.

3. Ar １ ~Ar ３ The organic light-emitting device according to claim 1 or 2, wherein each independently is phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl.

4. Ar １ ~Ar ３ at least one of is phenyl; The organic light-emitting device according to any one of claims 1 to 3, wherein the remainders are each independently phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl.

5. Ar １ ~Ar ３ at least one of is phenyl substituted with five deuteriums; The organic light-emitting element according to claim 1, wherein the remainder is unsubstituted phenyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, unsubstituted fluorenyl, unsubstituted 9,9-dimethylfluorenyl, unsubstituted 9,9-diphenylfluorenyl, unsubstituted carbazol-9-yl, or unsubstituted 9-phenyl-9H-carbazolyl.

6. Ar １ ~Ar ３ one of which is biphenyl substituted with 5 or more deuteriums, terphenyl substituted with 5 or more deuteriums, dibenzofuranyl substituted with 5 or more deuteriums, dibenzothiophenyl substituted with 5 or more deuteriums, fluorenyl substituted with 5 or more deuteriums, 9,9-dimethylfluorenyl substituted with 5 or more deuteriums, 9,9-diphenylfluorenyl substituted with 5 or more deuteriums, carbazol-9-yl substituted with 5 or more deuteriums, or 9-phenyl-9H-carbazolyl substituted with 5 or more deuteriums; The organic light-emitting device of claim 1 , wherein each remainder is independently unsubstituted phenyl or unsubstituted biphenyl.

7. Ar １ ~Ar ３ are each independently phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl; The Ar １ ~Ar ３ The organic light-emitting device according to claim 1 , wherein all of are fully substituted with deuterium.

8. The R １ The organic light-emitting device according to claim 1 , wherein all of are hydrogen.

9. The R １ The organic light-emitting device according to claim 1 , wherein at least five of are deuterium and the remainder are hydrogen.

10. The organic light-emitting device according to claim 1 , wherein the first compound is any one selected from the group consisting of: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】

11. Ar ４ The organic light-emitting device according to any one of claims 1 to 10, wherein is unsubstituted phenyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted fluorenyl, unsubstituted 9,9-dimethylfluorenyl, or unsubstituted 9,9-diphenylfluorenyl.

12. Ar ４ The organic light-emitting device according to claim 1 , wherein is unsubstituted phenyl, unsubstituted biphenyl or unsubstituted terphenyl.

13. R ２ The organic light-emitting device according to claim 1 , wherein all of are hydrogen.

14. The organic light-emitting device according to claim 1 , wherein the second compound is any one selected from the group consisting of: 【Chemistry 41】 【Chemistry 44】 【Chemistry 45】 【Chemistry 47】 【Chemistry 48】

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