NOVEL COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING THE SAME

Abstract

The present invention provides a novel compound and an organic light-emitting device containing the same.

Description

[Technical field]

[0001] [CROSS REFERENCE TO RELATED APPLICATIONS]

[0002] This application claims the benefit of priority based on Korean Patent Application No. 10-2019-0094225, filed on August 2, 2019, and all contents disclosed in the documents of said Korean patent application are incorporated herein by reference.

[0003] The present invention relates to a novel compound and an organic light-emitting device containing the same. [Background technology]

[0004] 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.

[0005] 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.

[0006] There is a continuing demand for the development of new organic materials for use in such organic light-emitting devices.

[0007] Therefore, the present invention provides a novel material for organic light emitting devices that can be used in solution processable organic light emitting devices. [Prior art documents] [Patent documents]

[0008] [Patent Document 1] Korean Patent Publication No. 10-2000-0051826 Summary of the Invention [Problem to be solved by the invention]

[0009] The present invention provides a novel compound and an organic light-emitting device containing the compound. [Means for solving the problem]

[0010] The present invention provides a compound represented by the following formula 1:

[0011] [Chemical formula 1]

[0012] [ka]

[0013] In the above chemical formula 1, A is a benzene ring fused to two adjacent 5-membered rings; Ar 1 , Ar 2 and Ar 3 at least one of the structures has a biphenylyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazol-9-yl, 9-methyl-carbazolyl, or 9-phenyl-carbazolyl structure, and the remainder has a phenyl structure, with the proviso that Ar 2 and Ar 3 However, both are not biphenylyl structures at the same time. The Ar 1 , Ar 2 and Ar 3 at least one of which is substituted with one or more deuterium atoms, and the remainder are unsubstituted; R is hydrogen; deuterium; halogen; cyano; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms;Substituted or unsubstituted aryl having 6 to 60 carbon atoms; or 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. ;Substituted or unsubstituted tri(alkyl having 1 to 60 carbon atoms)silyl; or Substituted or unsubstituted tri(aryl having 6 to 60 carbon atoms)silyl ; and n is an integer from 0 to 10.

[0014] The present invention also provides an organic light-emitting device including a first electrode, a second electrode facing the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one of the organic layers contains a compound represented by Chemical Formula 1. Effect of the Invention

[0015] The compound represented by the above-mentioned Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can improve the efficiency, lower the driving voltage, and / or improve the life characteristics of the organic light-emitting device. [Brief description of the drawings]

[0016] [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, a light-emitting layer 7, an electron injection and transport layer 8, and a negative electrode 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The present invention will now be described in more detail to aid in its understanding.

[0018] In this specification, [ka] denotes a bond that is connected to another substituent.

[0019] 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, cyano, nitro, hydroxy, carbonyl, ester, imide, amino, phosphine oxide, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfoxy, arylsulfoxy, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamine, aralkylamine, heteroarylamine, arylamine, arylphosphine, or heteroaryl 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-listed substituents. For example, the "substituent with two or more substituents connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent with two phenyl groups connected.

[0020] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but the number of carbon atoms is preferably 1 to 40. Specifically, the carbonyl group may have the following structure: base It may be, but is not limited to these.

[0021] [ka]

[0022] In the present 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. base It may be, but is not limited to these.

[0023] [ka]

[0024] In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferable that the number of carbon atoms is 1 to 25. Specifically, the imide group having the following structure is base It may be, but is not limited to these.

[0025] [ka]

[0026] 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.

[0027] 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.

[0028] As used herein, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0029] 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 methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, and isohexyl. 、4 Examples include, but are not limited to, -methylhexyl, and 5-methylhexyl.

[0030] 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.

[0031] 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.

[0032] 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 phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

[0033] 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.

[0034] As used herein, hetero Aryl is a heterostructure containing one or more of O, N, Si, and S as hetero elements. ring groupThe number of carbon atoms is not particularly limited, but preferably ranges from 2 to 60. Examples of heteroaryl include xanthene, thioxanthen, a thiophene group, a furanyl group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridinyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyrid ... Examples of such alkyl groups include, but are not limited to, dopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl groups.

[0035] In this specification, the above-mentioned explanation regarding the aryl group is applicable to the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, the arylamine group, and the arylsilyl group. In this specification, the above-mentioned explanation regarding the alkyl group is applicable to the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group. In this specification, the above-mentioned explanation regarding the heteroaryl 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 heteroaryl 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 heteroaryl is applicable to the heterocycle, except that it is not a monovalent group but is formed by bonding two substituents.

[0036] The present invention provides a compound represented by Chemical Formula 1.

[0037] Preferably, the compound is a compound represented by any one of the following chemical formulas 1-1 to 1-6:

[0038] [Chemical formula 1-1]

[0039] [ka]

[0040] [Chemical formula 1-2]

[0041] [ka]

[0042] [Chemical formula 1-3]

[0043] [ka]

[0044] [Chemical formula 1-4]

[0045] [ka]

[0046] [Chemical formula 1-5]

[0047] [ka]

[0048] [Chemical formula 1-6]

[0049] [ka]

[0050] In the above chemical formulas 1-1 to 1-6, Ar 1 , Ar 2 , Ar 3 , R and n are as defined in Chemical Formula 1 above.

[0051] In addition, in the above-mentioned Chemical Formula 1, the Ar 1 , Ar 2 and Ar 3 is replaced by one or more deuterium, preferably 1 , Ar 2 or Ar 3 is any one selected from the group consisting of the following chemical formulas 2-1 to 2-4:

[0052] [Chemical formula 2-1]

[0053] [ka]

[0054] [Chemical formula 2-2]

[0055] [ka]

[0056] [Chemical formula 2-3]

[0057] [ka]

[0058] [Chemical formula 2-4]

[0059] [ka]

[0060] In the above chemical formulas 2-1 to 2-4, X is O, S, -NR 1 or -CR 2 R 3 and R 1 , R 2 and R 3 are each independently hydrogen, methyl, or phenyl; Y 1 , Y 2 , Y 3 and Y 4 one of which is linked to the C in the triazinyl group or the N in the indolocarbazole structure, and the remaining is deuterium; Z 1 are all hydrogen or deuterium, and Z 2 are all hydrogen or deuterium, except Z 1 and Z 2 But neither of them is hydrogen.

[0061] Moreover, the chemical formula 2-1 is preferably any one selected from the group consisting of the following chemical formulas 2-1-1 to 2-1-4.

[0062] [Chemical formula 2-1-1]

[0063] [ka]

[0064] [Chemical formula 2-1-2]

[0065] [ka]

[0066] [Chemical formula 2-1-3]

[0067] [ka]

[0068] [Chemical formula 2-1-4]

[0069] [ka]

[0070] In the above chemical formulas 2-1-1 to 2-1-4, X 1 ~X 4 are each independently O, S, or -NR 1 or -CR 2 R 3 and R 1 , R 2 and R 3 are each independently hydrogen, methyl, or phenyl.

[0071] More preferably, the Ar 1 , Ar 2 or Ar 3 is any one selected from the group consisting of the following:

[0072] [ka]

[0073] Preferably, in the formula 1, the Ar 1 , Ar 2 and Ar 3 one of the Ar has a biphenylyl structure and the other has a phenyl structure; 1 , Ar 2 and Ar 3 At least one of is substituted with one or more deuterium atoms, and the remainder are unsubstituted.

[0074] Preferably, in the formula 1, the Ar 1 , Ar 2 and Ar 3 One of them is the following chemical formula 2- 3 and the remainder is unsubstituted phenyl:

[0075] [Chemical formula 2- 3 ]

[0076] [ka]

[0077] Above formula 2- 3 Inside, Z 1 are all deuterium, and Z 2 are all hydrogen.

[0078] Preferably, in the formula 1, the Ar 1 , Ar 2 and Ar 3 one of which is an unsubstituted biphenylyl, the rest having a phenyl structure, and at least one of which is represented by the following chemical formula 2- 4 It is expressed as:

[0079] [Chemical formula 2- 4 ]

[0080] [ka]

[0081] Preferably, in the formula 1, the Ar 1 has a biphenylyl structure, and the Ar 2 and Ar 3 one of the Ar 1 , Ar 2 and Ar 3 At least one of is substituted with one or more deuterium atoms, and the remainder are unsubstituted.

[0082] Preferably, in the formula 1, the Ar 1 , Ar 2 and Ar 3 is an unsubstituted dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, carbazol-9-yl, or 9-phenyl-carbazolyl group, the remainder have a phenyl structure, and at least one of the remainder is substituted with deuterium.

[0083] Preferably, in the formula 1, the Ar 1 , Ar 2 and Ar 3 One of the groups is a deuterium-substituted dibenzofuranyl, dibenzothiophenyl, or 9,9-dimethylfluorenyl, and the remaining groups are unsubstituted phenyl groups.

[0084] Preferably, all of the R's are hydrogen or all of the R's are deuterium. In this case, n is preferably an integer of 0 to 8.

[0085] Representative examples of the compound represented by Formula 1 are as follows:

[0086] [ka]

[0087]

change

[0088]

change

[0089]

change

[0090]

change

[0091]

change

[0092]

change

[0093]

change

[0094]

change

[0095]

change

[0096]

change

[0097]

change

[0098] [ka]

[0099] [ka]

[0100] [ka]

[0101] [ka]

[0102] [ka]

[0103] [ka]

[0104] [ka]

[0105] [ka]

[0106] [ka]

[0107] Meanwhile, the present invention provides a method for preparing the compound represented by the above-mentioned Formula 1, as shown in the following Reaction Scheme 1:

[0108] [Reaction Scheme 1]

[0109] [ka]

[0110] In the above reaction formula 1, A, R and n are as defined in Chemical Formula 1. B and E are one of the following, provided that B and E are not both one of the following at the same time: [ka] Ar 1 ', Ar 2 ' and Ar 3 ' at least one of the groups has a biphenylyl, dibenzofuranyl, dibenzothiophenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, carbazol-9-yl, 9-methyl-carbazolyl, or 9-phenyl-carbazolyl structure, and the remainder has a phenyl structure, with the proviso that Ar 2 ' and Ar 3 ' are not both biphenylyl structures at the same time, Ar 1 ', Ar 2 ' and Ar 3 At least one of the Ar 's is substituted with one or more deuterium atoms, and the rest are unsubstituted, or 1 ', Ar 2 ' and Ar 3 ' are all unsubstituted, D is a halogen group, more preferably bromine or chlorine.

[0111] As shown in Reaction Scheme 1, the compound represented by Chemical Formula 1 is prepared by an amine substitution reaction, and in Compound 1a and Compound 1b, Ar 1 ', Ar 2 ' and Ar 3 When all of the 's are unsubstituted, the amine substitution reaction of compound 1a with compound 1b is followed by a deuterium substitution reaction on the resulting reactant.

[0112] Specifically, Ar 1 ', Ar 2 ' and Ar3 In the case where at least one of the ' is substituted with one or more deuterium atoms and the remaining are unsubstituted, the compound 1a containing a core structure of a multi-condensed ring can be prepared by reacting the compound 1b containing a substituent substituted on the core structure in the presence of a palladium catalyst and a base. The reactive group for the amine substitution reaction can be changed according to those known in the art. The preparation method is further embodied in the preparation examples described below.

[0113] In the reaction of the compound 1a with the compound 1b, the palladium catalyst is bis(tri-tert-butylphosphine)palladium(0); Pd(P-tBu 3 ) 2 ), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II);Pd(dppf)C1 2 ) can be used in a molar ratio of 0.01 to 0.1 relative to 1 mole of compound 1a.

[0114] Examples of the base include inorganic bases such as potassium carbonate, sodium carbonate, and cesium carbonate; sodium tert-butoxide (NaOtBu); and tetraethylammonium hydroxide (Et 4 Examples of suitable bases include organic bases such as tetraethylammonium carbonate, bis(tetraethylammonium) carbonate, and triethylamine; and inorganic salts such as cesium fluoride. Any one of these bases or a mixture of two or more of them can be used. The base can be used in a molar ratio of 1 to 2, more specifically, 1.5 to 1.8, relative to 1 mole of the compound 1a containing the mother nucleus structure.

[0115] The reaction of compound 1a with compound 1b can be carried out in an organic solvent such as benzene, toluene, xylene, mesitylene, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidinone, dimethyl sulfoxide, etc., and is preferably carried out in tetrahydrofuran or toluene.

[0116] In addition, when Ar1', Ar2', and Ar3' are all unsubstituted in Compound 1a and Compound 1b, the compound represented by Chemical Formula 1 can be prepared by further carrying out a deuterium substitution reaction on the resulting reactant after the amine substitution reaction of Compound 1a and Compound 1b. In this case, the amine substitution reaction of Compound 1a and Compound 1b is as described above.

[0117] The deuterium substitution reaction is specifically carried out using PtO 2 In the presence of platinum-based catalysts such as 2 This can be carried out by adding O and carrying out the reaction.

[0118] Meanwhile, the compounds 1a and 1b used in the preparation of the compound represented by the above formula 1 can be prepared by a conventional method, and can also be commercially obtained and used.

[0119] For example, compound 1a can be produced by a reaction similar to that shown in Reaction Scheme 2 below.

[0120] [Reaction Scheme 2]

[0121] [ka]

[0122] In the above reaction formula 2, A, B, R and n are as defined in the above reaction formula 1, and D' is a halogen group, more preferably bromine or chlorine.

[0123] As shown in Reaction Scheme 2, compound 1a can be prepared by an amine substitution reaction between compound 1a-1 and compound 1a-2 containing a substituent for compound 1a. The amine substitution reaction is as described above.

[0124] The present invention also provides an organic light emitting device comprising the compound represented by Formula 1.

[0125] As an example, the present invention provides an organic light-emitting device including a first electrode, a second electrode provided opposite the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers contains a compound according to the present invention.

[0126] The organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate. The organic light emitting device according to the present invention may be an organic light emitting device having an inverted structure (inverted type) in which a negative electrode, one or more organic layers, and a positive electrode are sequentially stacked on a substrate. The organic layer includes one or more layers of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, and an electron transport layer. The organic layer may also include an electron injection and transport layer that simultaneously injects and transports electrons instead of the electron injection layer and the electron transport layer. The organic layer is a light-emitting layer.

[0127] For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIGS.

[0128] 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. In this structure, the compound represented by Chemical Formula 1 may be contained in the light-emitting layer.

[0129] 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 emitting layer 7, an electron injection and transport layer 8, and a negative electrode 4. In this structure, the compound represented by Chemical Formula 1 is contained in the hole injection layer, the hole transport layer, or the emitting layer. In addition, the structure may further include an electron blocking layer (not shown) between the hole transport layer and the emitting layer, and a hole blocking layer (not shown) between the emitting layer and the electron injection and transport layer.

[0130] The organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except for using the compound according to the present invention.

[0131] For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic layer, and an anode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, and an organic layer including at least one of a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer may be formed thereon, and then a material to be used as the anode may be deposited thereon.

[0132] In addition to this method, an organic light-emitting device can be produced by successively depositing a negative electrode material, an organic layer, and a positive electrode material on a substrate (WO2003 / 012890). However, the production method is not limited to this.

[0133] As an example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0134] 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 These include, but are not limited to: combinations of metals such as Sb with oxides; and conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0135] 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.

[0136] 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. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include 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 compounds, but are not limited thereto.

[0137] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer, and the hole transport material is a material that can receive holes from the positive electrode or the hole injection layer and move them to the light emitting layer, and is preferably a material with high mobility for holes.Specific examples include, but are not limited to, arylamine-based organic compounds, conductive compounds, and block copolymers having both conjugated and non-conjugated portions.

[0138] Meanwhile, an organic light emitting device according to an embodiment of the present invention may further include an electron blocking layer on the hole transport layer. The electron blocking layer is formed on the hole transport layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting hole mobility and preventing excessive movement of electrons to increase the probability of hole-electron binding. The electron blocking layer includes an electron blocking material, and examples of such electron blocking materials include, but are not limited to, arylamine-based organic materials.

[0139] The light-emitting layer includes a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, the condensed aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., and the heterocyclic ring-containing compound may be, but is not limited to, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, etc.

[0140] The dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene, which have 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.

[0141] In addition, the organic light emitting device according to the present invention may further include a compound represented by the following Chemical Formula 3 in the light emitting layer:

[0142] [Chemical formula 3]

[0143] [ka]

[0144] In the above chemical formula 3, Ar 4 and Ar 5each independently represents a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, R 4 and R 5 each independently represents hydrogen; deuterium; halogen; cyano; nitro; amino; a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; a substituted or unsubstituted alkenyl having 2 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 at least one selected from the group consisting of N, O, and S; a and b each independently represent an integer of 0 to 7.

[0145] Preferably, in the above Chemical Formula 3, Ar 4 and Ar 5 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or 9,9-dimethylfluorenyl.

[0146] Preferably, in the above Chemical Formula 3, R 4 and R 5 are all hydrogen. In this case, a and b are each an integer equal to 0.

[0147] Preferably, the compound represented by the formula 3 is any one selected from the group consisting of:

[0148] [ka]

[0149] [ka]

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] When the light emitting layer further contains the compound represented by Chemical Formula 3, the compound is contained in an amount of 20 to 80 parts by weight based on 100 parts by weight of the compound represented by Chemical Formula 1.

[0154] Meanwhile, an organic light emitting device according to an embodiment of the present invention may further include a hole blocking layer on the light emitting layer. The hole blocking layer is formed on the light emitting layer, preferably in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting electron mobility and preventing excessive movement of holes, thereby increasing the probability of hole-electron binding. The hole blocking layer includes a hole blocking material, and examples of the hole blocking material include compounds having an electron-withdrawing group introduced therein, such as triazine derivatives, pyrimidine derivatives, triazole derivatives, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives, but are not limited thereto.

[0155] An electron transport layer is formed on the light-emitting layer or on the hole blocking layer.

[0156] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. As the electron transport material, a material that can easily receive electrons injected from the negative electrode and transfer them to the light emitting layer and has high mobility for electrons is preferable. Specific examples include Al complex 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.

[0157] The electron injection layer is a layer that injects electrons from an electrode, and is capable of transporting electrons, has an excellent electron injection effect from a negative electrode, an excellent electron injection effect on the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and is preferably a compound with excellent thin-film forming ability.Specific examples of the compound include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0158] 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.

[0159] The organic light emitting device according to the present invention can be a front-emitting, a back-emitting or a dual-emitting type, depending on the materials used.

[0160] Furthermore, the compound according to the present invention can be included in an organic solar cell or an organic transistor other than the organic light-emitting device.

[0161] The compound represented by Formula 1 and the preparation of an organic light-emitting device including the same will be described in detail in the following examples, however, the following examples are merely illustrative of the present invention and are not intended to limit the scope of the present invention.

[0162] [Synthesis example]

[0163] Synthesis Example 1: Synthesis of Compound 1

[0164] Step 1) Synthesis of intermediate A

[0165] [ka]

[0166] In a three-neck flask, 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) (0.6 g, 1.2 mmol), sodium tert-butoxide (8.4 g, 87.8 mmol), and toluene (500 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 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).

[0167] Step 2) Synthesis of Compound 1

[0168] [ka]

[0169] In a three-neck flask, intermediate A (13.0 g, 38.5 mmol), intermediate 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), Toluene After adding 400 ml of the mixture, 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 in a 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 (7.9 g) was obtained by sublimation purification (yield 32%, MS [M+H] + =644).

[0170] Synthesis Example 2: Synthesis of Compound 2

[0171] [ka]

[0172] In step 1 of the synthesis example 1, 1-bromobenzene-2,3,4,5,6-d5 was replaced with bromobenzene to prepare intermediate B, and in step 2 of the synthesis example 1, intermediate B prepared above was used instead of intermediate A, and intermediate a was replaced with intermediate b. Compound 2 was prepared in the same manner as in the synthesis example 1 (MS [M+H] + =644).

[0173] Synthesis Example 3: Synthesis of Compound 3

[0174] [ka]

[0175] Compound 3 was prepared in the same manner as in the preparation of Compound 1, except that in step 2 of Synthesis Example 1, intermediate a was replaced with intermediate c (MS [M+H] + =649).

[0176] Synthesis Example 4: Synthesis of Compound 4

[0177] [ka]

[0178] In step 1 of Synthesis Example 1, 1-bromobenzene-2,3,4,5,6-d5 was replaced with bromo-1,1'-biphenyl to produce intermediate C, and in step 2 of Synthesis Example 1, Intermediates Compound 4 was prepared in the same manner as compound 1, except that intermediate C prepared above was used instead of A, and intermediate a was replaced with intermediate d (MS [M+H] + =649).

[0179] Synthesis Example 5: Synthesis of Compound 5

[0180] Step 1) Synthesis of Compound 5-1

[0181] [ka]

[0182] In a three-neck flask, intermediate C (15.0 g, 36.7 mmol), intermediate 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 Toluene After adding 400 ml of the mixture, 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 in a 2O 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 compound 5-1 (yield 65%, MS [M+H] + =715)

[0183] Step 2) Synthesis of Compound 5

[0184] [ka]

[0185] In a shaker tube, compound 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 5 was obtained by sublimation purification (yield 42%, deuterium substitution rate 82%, MS [M+H] + =749).

[0186] Synthesis Example 6: Synthesis of Compound 6

[0187] [ka]

[0188] Compound 6 was prepared in the same manner as in the preparation of Compound 1, except that in Step 2 of Synthesis Example 1, Intermediate A was replaced with Intermediate B, and Intermediate a was replaced with Intermediate f (MS [M+H] + =658).

[0189] Synthesis Example 7: Synthesis of Compound 7

[0190] [ka]

[0191] In step 1 of Synthesis Example 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 of Synthesis Example 1, intermediate A was replaced with intermediate D prepared above, and intermediate a was replaced with intermediate g. Compound 7 was prepared in the same manner as in the preparation of compound 1 (MS [M+H] + =660).

[0192] Synthesis Example 8: Synthesis of Compound 8

[0193] [ka]

[0194] Compound 8 was prepared in the same manner as in the preparation of Compound 1, except that in Step 2 of Synthesis Example 1, Intermediate A was replaced with Intermediate B, and Intermediate a was replaced with Intermediate h (MS [M+H] + =733).

[0195] Synthesis Example 9: Synthesis of Compound 9

[0196] [ka]

[0197] Compound 9 was prepared in the same manner as in the preparation of Compound 1, except that in step 1 of Synthesis Example 1, 11,12-dihydroindolo[2,3-a]carbazole was replaced with 5,8-dihydroindolo[2,3-c]carbazole (MS [M+H] + =644).

[0198] Synthesis Example 10: Synthesis of Compound 10

[0199] [ka]

[0200] In step 1 of Synthesis Example 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. In step 2 of Synthesis Example 1, intermediate A was replaced with intermediate F prepared above, and intermediate a was replaced with intermediate c. Except for this, compound 10 was prepared in the same manner as in the preparation of compound 1 (MS [M+H] + =644).

[0201] Synthesis Example 11: Synthesis of Compound 11

[0202] [ka]

[0203] In step 1 of Synthesis Example 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 of Synthesis Example 1, intermediate A was replaced with intermediate G prepared above, and intermediate a was replaced with intermediate i. Except for this, compound 11 was prepared in the same manner as in the preparation of compound 1 (MS [M+H] + =674).

[0204] Synthesis Example 12: Synthesis of Compound 12

[0205] Step 1) Synthesis of intermediate H

[0206] [ka]

[0207] In a three-neck flask, 5,12-dihydroindolo[3,2-a]carbazole (10.0 g, 39.0 mmol), intermediate 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 4 The 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).

[0208] Step 2) Synthesis of compound 12

[0209] [ka]

[0210] 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), Toluene After adding 250 ml of the mixture, 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 cooled 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 12 (5.4 g) was obtained by sublimation purification (yield 32%, MS [M+H] + =684).

[0211] Synthesis Example 13: Synthesis of Compound 13

[0212] [ka]

[0213] In step 1 of Synthesis Example 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. In step 2 of Synthesis Example 1, intermediate A was replaced with intermediate I prepared above, and intermediate a was replaced with intermediate k. Except for this, compound 13 was prepared in the same manner as in the preparation of compound 1 (MS [M+H] + =657).

[0214] Synthesis Example 14: Synthesis of Compound 14

[0215] [ka]

[0216] In step 1 of Synthesis Example 1, 11,12-dihydroindolo[2,3-a]carbazole was replaced with 5,8-dihydroindolo[2,3-c]carbazole, and 1-bromobenzene-2,3,4,5,6-d5 was replaced with bromobenzene to prepare intermediate L. Compound 14 was prepared in the same manner as in Synthesis Example 1, except that intermediate L prepared above was used instead of intermediate A in step 2 of Synthesis Example 1 (MS [M+H] + =639).

[0217] Example 1

[0218] A glass substrate coated with a 1,400 Å-thick thin film of ITO (indium tin oxide) was ultrasonically cleaned in distilled water with detergent dissolved in it. 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.

[0219] 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 blocking layer. Then, Compound 1 was used as a host for the light emitting layer, and 15 wt% GD of the host was used 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 in a ratio of 2:1 as an electron injection and transport layer, and then LiF and magnesium were vacuum deposited to a thickness of 30 Å in a ratio of 1:1. Magnesium and silver were deposited to a thickness of 160 Å on the electron injection and transport layer to form a negative electrode, and an organic light emitting device was manufactured.

[0220] [ka]

[0221] Examples 2 to 21 and Comparative Examples 1 to 12

[0222] Organic light emitting devices of Examples 2 to 21 and Comparative Examples 1 to 12 were fabricated in the same manner as in Example 1, except that the host material was changed to a compound shown in Table 1 below. When a mixture of two compounds was used as the host, the weight ratio between the host compounds is indicated in parentheses.

[0223] [ka]

[0224] <Test example: element characteristic evaluation>

[0225] The organic light emitting devices manufactured in Examples 1 to 21 and Comparative Examples 1 to 12 were heat-treated in an oven at 100° C. for 30 minutes, then removed from the oven and a current was applied to measure the voltage, efficiency and lifespan (T95). The results are shown in Table 1. 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%.

[0226] [Table 1]

[0227] [Table 1]

[0228] [Table 2]

[0229] When the compound GH-A of Comparative Example 1 is compared with the compounds 1 to 3 of Examples 1 to 3, it is found that the organic light-emitting devices containing the compounds of Examples 1 to 3 exhibit excellent long-life characteristics due to the substitution of deuterium. This is also found when the compound GH-B of Comparative Example 2 is compared with the compound 11 of Example 11. In addition, the compound GH-C of Comparative Example 3 has one deuterium, so the effect may not be very apparent, but the efficiency is reduced due to the intermediate phenyl ring between the dibenzofuran and triazine. It is found that the compounds of Comparative Examples 4 to 6 have a small molecular weight and a low glass transition temperature, which causes deformation of the device during heat treatment and deteriorates the device characteristics. The compounds GH-G and GH-H of Comparative Examples 7 and 8 are substances in which deuterium is substituted at a position other than the aromatic ring, and it is found that the effect of long life due to deuterium is not substantially exhibited, and rather the device characteristics are deteriorated due to the alkyl substituent that does not contribute to the movement of electrons. It was also found that in the compound GH-I of Comparative Example 9, even if deuterium was present in the aromatic ring, the alkoxy group, which does not contribute to the transfer of electrons, induced a deterioration in the device characteristics, and even if the alkoxy group was substituted with deuterium, the effect was not offset.

[0230] Example 1 4 As can be seen from the results of Example 21, the compound of Formula 1 was 3 When used in combination with the compound of formula 1, the effects of low voltage, high efficiency, and long life were even more pronounced. 3 When the compound of Chemical Formula 1 is mixed, the device characteristics are improved. 3 It was found that the stability of the exciplex formed was greatly improved, and the lifetime was further increased.

[0231] Therefore, when the compound of Chemical Formula 1 is used as the light-emitting layer of an organic electroluminescent device, a device with low voltage, high efficiency and long life can be obtained. [Explanation of symbols]

[0232] 1: Substrate 2: Positive electrode 3: Light-emitting layer 4: Negative electrode 5: Hole injection layer 6: Hole transport layer 7: Light-emitting layer 8: Electron injection and transport layer

Claims

1. Represented by the following chemical formula 1 Compound: [Chemical formula 1] 【Chemistry 1】 In the above chemical formula 1, A is a benzene ring fused to two adjacent 5-membered rings; R is deuterium; halogen; cyano; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted aryl having 6 to 60 carbon atoms; 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; substituted or unsubstituted tri(alkyl having 1 to 60 carbon atoms)silyl; or substituted or unsubstituted tri(aryl having 6 to 60 carbon atoms)silyl; n is an integer from 0 to 10; One of Ar 1 , Ar 2 and Ar 3 is any one selected from the group consisting of the following, and the rest are unsubstituted phenyl; 【Chemistry 2】

2. The compound is represented by any one of the following chemical formulas 1-1 to 1-6: The compound of claim 1: [Chemical formula 1-1] 【Chemistry 2】 [Chemical formula 1-2] 【Chemistry 3】 [Chemical formula 1-3] 【Chemistry 4】 [Chemical formula 1-4] 【Chemistry 5】 [Chemical formula 1-5] 【Chemistry 6】 [Chemical formula 1-6] 【Chemistry 7】 In the above chemical formulas 1-1 to 1-6, Ar １ , Ar ２ , Ar ３ , R and n are as defined in claim 1.

3. A compound represented by the following chemical formula 1: Compound: [Chemical formula 1] 【Chemistry 1】 In the above chemical formula 1, A is a benzene ring fused to two adjacent 5-membered rings; R is deuterium; halogen; cyano; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted aryl having 6 to 60 carbon atoms; 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; substituted or unsubstituted tri(alkyl having 1 to 60 carbon atoms)silyl; or substituted or unsubstituted tri(aryl having 6 to 60 carbon atoms)silyl; n is an integer from 0 to 10; Ar １ , Ar ２ and Ar ３ one of which is unsubstituted biphenylyl and the rest are phenyl; At least one of the remainders is represented by the following formula 2-4. [Chemical formula 2-4] 【Chemistry 14】

4. A compound represented by the following chemical formula 1: Compound: [Chemical formula 1] 【Chemistry 1】 In the above chemical formula 1, A is a benzene ring fused to two adjacent 5-membered rings; R is deuterium; halogen; cyano; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted aryl having 6 to 60 carbon atoms; 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; substituted or unsubstituted tri(alkyl having 1 to 60 carbon atoms)silyl; or substituted or unsubstituted tri(aryl having 6 to 60 carbon atoms)silyl; n is an integer from 0 to 10; Ar １ is biphenylyl, Ar ２ and Ar ３ one of which is biphenylyl and the rest are phenyl; At least one of Ar 1 , Ar 2 and Ar 3 has all hydrogen replaced with deuterium.

5. A compound represented by the following chemical formula 1: Compound: [Chemical formula 1] 【Chemistry 1】 In the above chemical formula 1, A is a benzene ring fused to two adjacent 5-membered rings; R is deuterium; halogen; cyano; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted aryl having 6 to 60 carbon atoms; 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; substituted or unsubstituted tri(alkyl having 1 to 60 carbon atoms)silyl; or substituted or unsubstituted tri(aryl having 6 to 60 carbon atoms)silyl; n is an integer from 0 to 10; Ar １ , Ar ２ and Ar ３ is unsubstituted dibenzofuranyl, dibenzothiophenyl, or 9,9-dimethylfluorenyl; The remainder is phenyl, At least one of the remainder has all hydrogens replaced with deuterium.

6. A compound represented by the following chemical formula 1: Compound: [Chemical formula 1] 【Chemistry 1】 In the above chemical formula 1, A is a benzene ring fused to two adjacent 5-membered rings; R is deuterium; halogen; cyano; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl having 2 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted aryl having 6 to 60 carbon atoms; 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; substituted or unsubstituted tri(alkyl having 1 to 60 carbon atoms)silyl; or substituted or unsubstituted tri(aryl having 6 to 60 carbon atoms)silyl; n is an integer from 0 to 10; Ar １ , Ar ２ and Ar ３ one of which is dibenzofuranyl, dibenzothiophenyl or 9,9-dimethylfluorenyl substituted with deuterium; The remainder are unsubstituted phenyl groups.

7. All of the R's are deuterium. A compound according to any one of claims 1 to 6.

8. The compound represented by the formula 1 is any one selected from the group consisting of: A compound according to any one of claims 1, 3 to 6: 【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 Formula 33】 【Chemistry 35】

9. A first electrode; a second electrode provided opposite to the first electrode; one or more organic layers provided between the first electrode and the second electrode; Includes An organic light-emitting device, At least one of the organic layers comprises a compound according to any one of claims 1 to 8. Organic light-emitting devices.

10. The organic layer is a light-emitting layer. The organic light-emitting device according to claim 9 .

11. The light-emitting layer further includes a compound represented by the following Chemical Formula 3: The organic light-emitting device according to claim 10: [Chemical formula 3] 【Chemical 36】 In the above chemical formula 3, Ar ４ and Ar ５ each independently represents a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms containing at least one selected from the group consisting of N, O, and S, R ４ and R ５ each independently represents deuterium; halogen; cyano; nitro; amino; a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; a substituted or unsubstituted alkenyl having 2 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 at least one selected from the group consisting of N, O, and S; a and b each independently represent an integer of 0 to 7.

12. Ar ４ and Ar ５ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, or 9,9-dimethylfluorenyl; The organic light-emitting device according to claim 11 .

13. The compound represented by the formula 3 is any one selected from the group consisting of: The organic light-emitting device according to claim 11 : 【Chemical 37】 【Chemical 38】 【Chemical Formula 39】 【Chemistry 40】 【Chemistry 41】

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