Novel compounds and organic light-emitting devices comprising the same

Abstract

The present invention provides novel compounds and organic light emitting devices comprising the same.

Description

TECHNICAL FIELD

[0001] Cross Reference to Related Applications

[0002] This application claims priority based on Korean Patent Application No. 10-2021-0030416 filed on March 8, 2021 and Korean Patent Application No. 10-2022-0029047 filed on March 8, 2022, the entire contents of which are incorporated herein by reference as part of the present specification.

[0003] The present application relates to a novel compound and an organic light emitting device comprising the same. BACKGROUND

[0004] Generally, an organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using organic substances. An organic light emitting device using the organic light emitting phenomenon has wide viewing angle, excellent contrast, fast response time, and is excellent in luminance, driving voltage, and response speed characteristics, and thus is being studied a lot.

[0005] An organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed of a multi-layer structure using different substances, respectively, for example, can be formed of a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, etc. For such a structure of the organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons are formed, and when the excitons re-traverse to a ground state, light is emitted.

[0006] There is a continuous demand for development of new materials for the organic substances used in the organic light emitting device as described above.

[0007] On the other hand, in recent years, in order to save process costs, an organic light emitting device using a solution process, particularly an inkjet process, instead of an existing evaporation process, is being developed. Initially, it was intended to develop an organic light emitting device by coating all organic light emitting device layers using a solution process, but the current technology has limitations, and thus a hybrid process in which only HIL, HTL, and EML are coated using a solution process, and subsequent processes are performed using an existing evaporation process, is being studied.

[0008] Accordingly, the present application provides a novel material for an organic light emitting device that can be used in an organic light emitting device while being able to use a solution process.

[0009] PRIOR ART DOCUMENTS​

[0010] Patent Literature

[0011] (Patent Literature 1) Korean Patent Publication No. 10-2000-0051826 SUMMARY

[0012] Technical Problem

[0013] The present application relates to a novel compound and an organic light emitting device comprising the same.

[0014] Solution to Problem

[0015] The present application provides a compound represented by the following Chemical Formula 1 or 2:

[0016] [Chemical Formula 1]

[0017]

[0018] [Chemical Formula 2]

[0019]

[0020] In the above Chemical Formula 1 and 2,

[0021] X1 to X3 are each independently CH or N, and at least one of X1 to X3 is N,

[0022] Y is O or S,

[0023] Ar is a substituted or unsubstituted C 1-30 alkyl; a substituted or unsubstituted C 3-30 cycloalkyl; a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl,

[0024] L1 and L2 are each independently a single bond, phenylene, biphenylene, or terphenylene.

[0025] R1 and R2 are each independently hydrogen; deuterium; a halogen; a cyano; a substituted or unsubstituted C 1-60 alkyl; a substituted or unsubstituted C 6-60 aryl; or a substituted or unsubstituted C 2-60 heteroaryl,

[0026] m is an integer of 1 to 7, and n is an integer of 1 to 8,

[0027] the above Ar is substituted with one or more deuterium, or at least one of the above R1 and R2 is deuterium,

[0028] The compound represented by Chemical Formula 1 or 2 contains four or more deuteriums in the compound.

[0029] In addition, the present application provides an organic light emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound represented by Chemical Formula 1 or 2.

[0030] Effects of the Invention

[0031] The compound represented by Chemical Formula 1 or 2 can be used as a material for an organic layer of an organic light emitting device, and can be used in a solution process, and can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifetime characteristics in an organic light emitting device. BRIEF DESCRIPTION OF DRAWINGS

[0032] Figure 1 An example of an organic light emitting device composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4 is shown.

[0033] Figure 2 An example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light emitting layer 8, a hole blocking layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4 is shown. DETAILED DESCRIPTION

[0034] Hereinafter, the present application will be described in more detail.

[0035] (Definitions of Terms)

[0036] In the present specification, or represents a bond to another substituent. In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from the group consisting of deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphonic acid group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; an alkylsulfinyl group; an arylsulfinyl group; an alkylsulfonyl group; an arylsulfonyl group; a silane group; and an organometallic group.

[0037] arylthio group alkylsulfonyl group arylsulfonyl group arylthio group one or more substituents selected from the group consisting of a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; an aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamino group; an aryl phosphine group; or a heteroaryl group containing one or more of N, O, and S atoms, or one or more substituents selected from the group consisting of the above-mentioned substituents, or one or more substituents in which two or more of the above-mentioned substituents are linked. For example, the "one or more substituents in which two or more of the above-mentioned substituents are linked" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or can be interpreted as a substituent in which two phenyl groups are linked.

[0038] In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the above-mentioned carbonyl group can have a structure represented by the following formula, but is not limited thereto.

[0039]

[0040] In the present specification, in the ester group, the oxygen of the ester group can 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 above-mentioned ester group can have a structure represented by the following formula, but is not limited thereto.

[0041]

[0042] In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the above-mentioned imide group can have a structure represented by the following formula, but is not limited thereto.

[0043]

[0044] In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyl dimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto.

[0045] In the present specification, the boron group specifically includes a dimethylboron group, a diethylboron group, a t-butyldimethylboron group, a diphenylboron group, a phenylboron group, and the like, but is not limited thereto.

[0046] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

[0047] In the present specification, the above-mentioned alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably from 1 to 40. According to one embodiment, the number of carbon atoms of the above-mentioned alkyl group is from 1 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is from 1 to 10. According to another embodiment, the number of carbon atoms of the above-mentioned alkyl group is from 1 to 6. As specific examples of the alkyl group, there are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-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, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, iso-hexyl, 2-methylhexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

[0048] In the present specification, the above-mentioned alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 40. According to one embodiment, the number of carbon atoms of the above-mentioned alkenyl group is from 2 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is from 2 to 10. According to another embodiment, the number of carbon atoms of the above-mentioned alkenyl group is from 2 to 6. As specific examples, there are ethenyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butanedienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphen-1-yl)ethen-1-yl, stilbenyl, styryl, and the like, but are not limited thereto.

[0049] In the present specification, the above-mentioned cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having from 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is from 3 to 30. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is from 3 to 20. According to another embodiment, the number of carbon atoms of the above-mentioned cycloalkyl group is from 3 to 6. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-t-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

[0050] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0051] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure. When the fluorene group is substituted as described above, it can become... etc., but not limited to this.

[0052] In this specification, a heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heteroelements. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include xanthene, thioxanthen, thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso Azolyl, thiadiazolyl, phenthiazinyl, and dibenzofuranyl groups, but not limited to these.

[0053] In the present specification, the aryl group in aralkyl group, aralkenyl group, alkylaryl group, arylamine group, arylsilyl group is the same as the exemplification of the aryl group described above. In the present specification, the alkyl group in aralkyl group, alkylaryl group, alkylamine group is the same as the exemplification of the alkyl group described above. In the present specification, the heteroaryl group in heteroarylamine group can be applied to the description of the heteroaryl group described above. In the present specification, the alkenyl group in aralkenyl group is the same as the exemplification of the alkenyl group described above. In the present specification, the arylene group is a 2-valent group, and in addition thereto, the description of the aryl group described above can be applied. In the present specification, the heteroarylene group is a 2-valent group, and in addition thereto, the description of the heteroaryl group described above can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group, but is a 2-valent group in which two substituents are bonded, and in addition thereto, the description of the aryl group or the cycloalkyl group described above can be applied. In the present specification, the hetero ring is not a 1-valent group, but is a 2-valent group in which two substituents are bonded, and in addition thereto, the description of the heteroaryl group described above can be applied.

[0054] (Compound)

[0055] The present application provides a compound represented by the above Chemical Formula 1 or 2.

[0056] The compound represented by the above Chemical Formula 1 or 2 contains 4 or more deuteriums in the compound, preferably 4 to 30 deuteriums, more preferably 4 to 20 deuteriums, further more preferably 4 to 15 deuteriums.

[0057] In addition, in the above Chemical Formula 1 and 2, preferably, each of X1 to X3 is N.

[0058] In addition, in the above Chemical Formula 1 and 2, preferably, Ar is C 6-20 In addition, in the above Chemical Formula 1 and 2, preferably, Ar is C

[0059] More preferably, Ar is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenylnaphthyl group, a naphthylphenyl group, a phenanthryl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, or a triphenylenyl group, and the above Ar is not substituted or substituted with 5 to 13 deuteriums. Further more preferably, the above Ar is not substituted or substituted with 5, 9, 11, or 13 deuteriums.

[0060] In addition, in the above Chemical Formula 1 and 2, preferably, L1 is a single bond, a phenylene group, a biphenylene group, or a terphenylene group, and L2 is a single bond; or L1 is a single bond, and L2 is a phenylene group or a biphenylene group.

[0061] In addition, in the above Chemical Formula 1 and 2, preferably, each of R1 and R2 is independently hydrogen or deuterium.

[0062] More preferably, R1and R2are each hydrogen; or R1is deuterium and R2is hydrogen, m is an integer of 4, 6 or 7, and n is an integer of 8; or R1is hydrogen and R2is deuterium, m is an integer of 7, and n is an integer of 4, 6 or 8; or R1and R2are each deuterium, m is an integer of 4, 6 or 7, and n is an integer of 4, 6 or 8.

[0063] Further, more preferably, in the above Chemical Formulas 1 and 2, Ar is phenyl, biphenyl, terphenyl or triphenylene, the above Ar is substituted with 5 to 13 deuteriums, and R1and R2are each hydrogen. More preferably, in this case, the above Ar is phenyl substituted with 5 deuteriums, biphenyl substituted with 5 or 9 deuteriums, terphenyl substituted with 5 or 13 deuteriums, or triphenylene substituted with 11 deuteriums, and R1and R2are each hydrogen.

[0064] Further, more preferably, in the above Chemical Formulas 1 and 2, Ar is phenyl, biphenyl, terphenyl or triphenylene, the above Ar is not substituted, and at least one of R1and R2is deuterium and the rest is hydrogen. In this case, m is an integer of 1 to 7, and n is an integer of 1 to 8. The compound represented by the above Chemical Formula 1 or 2 contains 4 to 15 deuteriums in the compound. More preferably, in this case, Ar is phenyl, biphenyl, terphenyl or triphenylene, the above Ar is not substituted, R1is deuterium and R2is hydrogen, m is an integer of 4, 6 or 7, and n is an integer of 8; or R1is hydrogen and R2is deuterium, m is an integer of 7, and n is an integer of 4, 6 or 8; or R1and R2are each deuterium, m is an integer of 4, 6 or 7, and n is an integer of 4, 6 or 8.

[0065] Further, more preferably, in the above Chemical Formulas 1 and 2, the above Ar is substituted with one or more deuteriums, and at least one of the above R1and R2is deuterium. Specifically, the above Ar is phenyl, biphenyl, terphenyl or triphenylene, the above Ar is substituted with 5 to 13 deuteriums, and at least one of R1and R2is deuterium and the rest is hydrogen. In this case, m is an integer of 1 to 7, and n is an integer of 1 to 8. More preferably, in this case, the above Ar is phenyl substituted with 5 deuteriums, biphenyl substituted with 5 or 9 deuteriums, terphenyl substituted with 5 or 13 deuteriums, or triphenylene substituted with 11 deuteriums, R1is deuterium, R2is hydrogen, m is an integer of 4, 6 or 7, and n is an integer of 8; or R1is hydrogen, R2is deuterium, m is an integer of 7, and n is an integer of 4, 6 or 8; or R1and R2are each deuterium, m is an integer of 4, 6 or 7, and n is an integer of 4, 6 or 8.

[0066] Representative examples of the compound represented by the above Chemical Formula 1 or 2 are shown below:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] In another aspect, as one example, the present application provides a method for producing the compound represented by Chemical Formula 1 as shown in Reaction Formula 1 below, and the compound represented by Chemical Formula 2 can also be produced by applying the following reaction formula.

[0076] [Reaction Formula 1]

[0077]

[0078] In Reaction Formula 1 above, the definitions of the other components except for X and Z are the same as the definitions described above, and X and Z are each independently halogen, preferably bromine or chlorine.

[0079] The reactions in Steps S11 and S12 above are amine substitution reactions, and are preferably performed in the presence of a palladium catalyst and a base, and the reaction group used for the amine substitution reaction can be changed according to techniques known in the technical field.

[0080] In addition, as another example, the present application provides a method for producing the compound represented by Chemical Formula 1 as shown in Reaction Formula 2 below, and the compound represented by Chemical Formula 2 can also be produced by applying the following reaction formula.

[0081] [Reaction Formula 2]

[0082]

[0083] In Reaction Formula 2 above, the definitions of the other components except for Z are the same as the definitions described above, and Z is halogen, preferably bromine or chlorine.

[0084] The reaction between Compound (iii) and Compound (iv) in Step S21 above is an amine substitution reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reaction group used for the amine substitution reaction can be changed according to techniques known in the technical field.

[0085] Further, as another example, a production method of the compound represented by the above Chemical Formula 1 as shown in the following Reaction Formula 3 can be performed by applying the following Reaction Formula to the compound represented by Chemical Formula 2.

[0086] [Reaction Formula 3]

[0087]

[0088] In the above Reaction Formula 3, the definitions of the other than W1, W2, and V are the same as the above. W1and W2are each independently halogen, preferably bromine or chlorine. V is a boron-containing organic group such as a boronic acid group, a boronic ester group, or a boronic pinacol ester group.

[0089] In the above Reaction Formula 3, the reaction of the compound (iv) with the compound (v) in the step S31 is an amine substitution reaction, which is preferably performed in the presence of a palladium catalyst and a base, and the reaction group for the amine substitution reaction can be changed according to the techniques known in the technical field.

[0090] Further, the reaction of the compound (vi) with the compound (vii) in the step S32 is a Suzuki-coupling reaction, which is preferably performed in the presence of a palladium catalyst and a base, and the reaction group for the Suzuki-coupling reaction can be changed according to the techniques known in the technical field.

[0091] The above production method can be more specifically described in the following synthesis examples.

[0092] (Organic light emitting device)

[0093] Further, the present application provides an organic light emitting device including the compound represented by the above Chemical Formula 1 or 2. As one example, the present application provides an organic light emitting device including: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers including the compound represented by the above Chemical Formula 1 or 2.

[0094] The organic layers of the organic light emitting device of the present application can be formed of a single layer structure, or can be formed of a multi-layer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present application can have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron injection and transport layer which simultaneously performs electron injection and transport, as the organic layers. However, the structure of the organic light emitting device is not limited thereto, and can include a smaller number of organic layers.

[0095] Further, the organic material layer described above can include a light-emitting layer, and the light-emitting layer contains the compound represented by Chemical Formula 1 or 2. In particular, the compound according to the present application can be used as a host of the light-emitting layer.

[0096] Further, the organic light-emitting device according to the present application can be an organic light-emitting device of a normal type in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present application can be an organic light-emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, a structure of the organic light-emitting device according to an embodiment of the present application is illustrated in FIGS. 1 to 3. Figure 1 and 2

[0097] Figure 1 FIG. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, an organic material layer 3, and a cathode 4. In the structure described above, the compound represented by Chemical Formula 1 or 2 can be contained in the light-emitting layer described above.

[0098] Figure 2 FIG. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole blocking layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4. In the structure described above, the compound represented by Chemical Formula 1 or 2 can be contained in the light-emitting layer described above.

[0099] The organic light-emitting device according to the present application can be manufactured using materials and methods known in the technical field, except that the compound represented by Chemical Formula 1 or 2 is contained in one or more of the organic material layers described above. In addition, when the organic light-emitting device described above includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0100] For example, the organic light-emitting device according to the present application can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, it can be manufactured by forming an anode by evaporating a metal or a metal oxide having conductivity or an alloy thereof on a substrate using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation, then forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then evaporating a material that can be used as a cathode on the organic material layer.

[0101] ​In addition, the compound represented by the above formula 1 or 2 can be used not only in the vacuum evaporation method but also in a solution coating method to form an organic layer when manufacturing an organic light emitting device. Here, the solution coating method refers to a spin coating method, a dip coating method, a blade coating method, an inkjet printing method, a screen printing method, a spray method, a roll coating method, and the like, but is not limited thereto. In addition to these methods, an organic light emitting device can be manufactured by sequentially evaporating a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited thereto.

[0102] As one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0103] As the anode material, a material having a large work function is generally preferred in order to smoothly inject holes into the organic layer. As specific examples of the anode material, there are metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; combinations of a metal and an oxide such as ZnO:Al or SnO2:Sb; conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polyaniline, or the like, but are not limited thereto.

[0104] As the cathode material, a material having a small work function is generally preferred in order to easily inject electrons into the organic layer. As specific examples of the cathode material, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; a multi-layered structure material such as LiF / Al or LiO2 / Al, or the like, but are not limited thereto.

[0105] The hole injection layer is a layer that injects holes from the electrode, and as a hole injection material, a compound having a capability of transporting holes, an effect of injecting holes from the anode, an excellent hole injection effect to the light emitting layer or light emitting material, a capability of preventing excitons generated in the light emitting layer from migrating to the electron injection layer or electron injection material, and an excellent film formation capability is preferred. In particular, it is preferred that the HOMO (highest occupied molecular orbital) of the hole injection material be between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of the hole injection material, there are conductive compounds such as metal porphyrin, oligothiophene, arylamine-based organic material, hexacyno hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, and polythiophene, but are not limited thereto.

[0106] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a substance having a large mobility for holes is suitable. As specific examples, there are arylamine-based organic compounds, electrically conductive compounds, and block copolymers having both a conjugated portion and a non-conjugated portion, but are not limited thereto.

[0107] The electron suppression layer is a layer that is formed on the hole transport layer, is preferably provided in contact with the light-emitting layer, and functions to improve the efficiency of the organic light-emitting device by adjusting the hole mobility and preventing excessive migration of electrons to increase the probability of combination between holes and electrons. The electron suppression layer contains an electron blocking substance, and as examples of such an electron blocking substance, arylamine-based organic compounds and the like can be used, but are not limited thereto.

[0108] The light-emitting layer is located between the anode and the cathode and contains the compound of Chemical Formula 1 or 2 as a host substance. Therefore, excitons are uniformly emitted throughout the light-emitting layer, so that the organic light-emitting device exhibits low voltage driving and high light-emitting efficiency, and can also exhibit significantly improved lifetime characteristics.

[0109] In addition, the light-emitting layer can contain a commonly used host substance (hereinafter referred to as a second host) in addition to the compound of Chemical Formula 1 or 2. Specifically, the second host is an aromatic condensed ring derivative or a heterocycle-containing compound, etc. Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocycle-containing compound, there are carbazole derivatives, diphenylfuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0110] On the other hand, the light-emitting layer can contain a dopant substance in addition to the host substance. As such a dopant substance, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and there are pyrene, anthracene, phenanthrene, fluoranthene, etc., having an arylamino group, but are not limited thereto. The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted with one or two or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups, or is unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, as the metal complex, there are iridium complexes, platinum complexes, etc., but are not limited thereto. ​​

[0111] The hole blocking layer refers to a layer formed on the light emitting layer, preferably disposed in contact with the light emitting layer, which improves the efficiency of the organic light emitting device by preventing the excessive migration of holes to increase the probability of combination between holes and electrons by adjusting the electron mobility. The hole blocking layer contains a hole blocking substance, and as examples of such a hole blocking substance, compounds into which an electron withdrawing group is introduced, such as azine derivatives containing triazine, triazole derivatives, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, etc. can be used, but are not limited thereto. The hole blocking layer refers to a layer formed on the light emitting layer, preferably disposed in contact with the light emitting layer, which improves the efficiency of the organic light emitting device by preventing the excessive migration of holes to increase the probability of combination between holes and electrons by adjusting the electron mobility. The hole blocking layer contains a hole blocking substance, and as examples of such a hole blocking substance, compounds into which an electron withdrawing group is introduced, such as azine derivatives containing triazine, triazole derivatives, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, etc. can be used, but are not limited thereto.

[0112] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, formed on the light emitting layer or the hole blocking layer. The electron transport substance contained in the electron transport layer is a substance that can receive electrons from the cathode and transport them to the light emitting layer, and a substance having a large mobility for electrons is suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited thereto. In addition, it can be used together with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthracene ketone, etc. and their derivatives, metal coordination compounds, or nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto. The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, formed on the light emitting layer or the hole blocking layer. The electron transport substance contained in the electron transport layer is a substance that can receive electrons from the cathode and transport them to the light emitting layer, and a substance having a large mobility for electrons is suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited thereto. In addition, it can be used together with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthracene ketone, etc. and their derivatives, metal coordination compounds, or nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto. The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, formed on the light emitting layer or the hole blocking layer. The electron transport substance contained in the electron transport layer is a substance that can receive electrons from the cathode and transport them to the light emitting layer, and a substance having a large mobility for electrons is suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited thereto. In addition, it can be used together with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthracene ketone, etc. and their derivatives, metal coordination compounds, or nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto.

[0113] In addition, the electron injection layer is formed on the electron transport layer, and as the electron injection substance contained in the electron injection layer, there are LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthracene ketone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto. The electron injection layer is formed on the electron transport layer, and as the electron injection substance contained in the electron injection layer, there are LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthracene ketone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto. The electron injection layer is formed on the electron transport layer, and as the electron injection substance contained in the electron injection layer, there are LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthracene ketone, etc. and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto.

[0114] As the metal coordination compound, there are lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinoline), zinc bis(10-hydroxybenzo[h]quinoline), gallium bis(2-methyl-8-quinoline) chloride, gallium bis(2-methyl-8-quinoline)(o-cresol), aluminum bis(2-methyl-8-quinoline)(o-naphthol), gallium bis(2-methyl-8-quinoline)(2-naphthol), etc., but are not limited thereto.

[0115] On the other hand, the organic light emitting device described above can also include an electron injection and transport layer which injects electrons from an electrode and transports the received electrons to a light emitting layer, instead of the electron transport layer and the electron injection layer described above, while playing the roles of the electron transport layer and the electron injection layer. Such an electron injection and transport material can use the electron injection material or the electron transport material described above.

[0116] The organic light emitting device according to the present application can be a top emission type, a bottom emission type, or a bidirectional emission type, depending on the materials used.

[0117] In addition, the compound according to the present application can be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.

[0118] Hereinafter, preferred examples are suggested in order to help the understanding of the present application. However, the following examples are only for illustrating the present application, and the scope of the present application is not limited to the following examples.

[0119] Synthesis Example 1: Synthesis of Compound 1

[0120]

[0121] 1) Synthesis of Compound A-1

[0122] Under a nitrogen atmosphere, 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (20 g, 63.3 mmol) and (phenyl-d5)boronic acid (8 g, 63.3 mmol) were added to 400 ml of toluene, stirred and refluxed. Then, potassium carbonate (26.2 g, 189.8 mmol) was dissolved in 79 ml of water and added, after sufficient stirring, bis(tri-tert-butylphosphine)palladium (1 g, 1.9 mmol) was added. After 6 hours of reaction, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in 1148 mL of tetrahydrofuran (an amount of 50 times the total volume of the product described above), washed with water 2 times, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using tetrahydrofuran and ethyl acetate, thereby obtaining a white solid compound A-1 (13.1 g, 57%, MS: [M+H] = 363.8). +

[0123] 2) Synthesis of Compound B-1

[0124] ​Compound A-1 (10 g, 27.6 mmol) and 2-bromo-9H-carbazole (6.8 g, 27.6 mmol) were added to 100 ml of dimethylacetamide under a nitrogen atmosphere, stirred and refluxed. Then, potassium phosphate tribasic (17.6 g, 82.7 mmol) was added, warmed and stirred. After 2 hours of reaction, the resulting solid was filtered after cooling to room temperature. The solid obtained as a result was dissolved in 473 mL of chloroform (an amount corresponding to 30 times the total volume of the solid), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate, thereby obtaining white solid compound B-1 (11.8 g, 75%, MS: [M+H + = 573.5).

[0125] 3) Synthesis of Compound 1

[0126] Compound B-1 (20 g, 34.9 mmol) and 9H-carbazole (5.8 g, 34.9 mmol) were added to 400 ml of xylene under a nitrogen atmosphere, stirred and refluxed. Then, potassium phosphate tribasic (10.1 g, 104.8 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (0.5 g, 1 mmol) was added. After 2 hours of reaction, the organic layer was filtered to remove the salt after cooling to room temperature, and the filtered organic layer was distilled. The resulting product was dissolved in 230 mL of chloroform (an amount corresponding to 10 times the total volume of the product), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate, thereby obtaining white solid compound 1 (12.9 g, 56%, MS: [M+H + = 659.8).

[0127] Synthesis Example 2: Synthesis of Compound 2

[0128]

[0129] 1) Synthesis of Compound A-2

[0130] Under a nitrogen atmosphere, 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (20 g, 79 mmol) and 9H-carbazole (13.2 g, 79 mmol) were added to 400 ml of xylene, stirred and refluxed. Then, potassium phosphate tribasic (22.8 g, 237 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (1.2 g, 2.4 mmol) was added. After 3 hours of reaction, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. The obtained product was dissolved again in 268 mL of chloroform (10 times the amount of the total volume of the product described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica gel column with chloroform and ethyl acetate, thereby obtaining a white solid compound A-2 (19 g, 71%, MS: [M+H + = 340.5).

[0131] 2) Synthesis of Compound 2

[0132] Under a nitrogen atmosphere, compound A-2 (20 g, 58.9 mmol) and 2-(4-chlorophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (25.6 g, 58.9 mmol) were added to 400 ml of xylene, stirred and refluxed. Then, potassium phosphate tribasic (17 g, 176.8 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (0.9 g, 1.8 mmol) was added. After 4 hours of reaction, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. The obtained product was dissolved again in 434 mL of chloroform (10 times the amount of the total volume of the product described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate, thereby manufacturing a white solid compound 2 (23.9 g, 55%, MS: [M+H + = 737.9).

[0133] Synthesis Example 3: Synthesis of Compound 3

[0134]

[0135] 1) Synthesis of Compound A-3

[0136] Under a nitrogen atmosphere, 4,4,5,5-tetramethyl-2-(triphenylen-2-yl-d11)-1,3,2- dioxaborolane (20 g, 54.7 mmol) and 2,4-dichloro-6-(dibenzo[b,d]thiophen-3-yl)-1,3,5- triazine (18.2 g, 54.7 mmol) were added to 400 ml of toluene, stirred and refluxed. Then, potassium carbonate (22.7 g, 164.2 mmol) was dissolved in 68 ml of water and added, after sufficient stirring, bis(triphenylphosphine)palladium (0.8 g, 1.6 mmol) was added. After 8 hours of reaction, the organic layer and the aqueous layer were separated after cooling to room temperature, and the organic layer was distilled. The obtained product was dissolved in 1465 ml of tetrahydrofuran (50 times the amount of the total volume of the product described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with tetrahydrofuran and ethyl acetate, thereby obtaining a white solid compound A-3 (21.1 g, 72%, MS: [M+H + = 536.1).

[0137] 2) Synthesis of compound 3

[0138] Under a nitrogen atmosphere, compound A-3 (20 g, 37.4 mmol) and 9H-2,9'- bicarbazole (12.4 g, 37.4 mmol) were added to 400 ml of xylene, stirred and refluxed. Then, potassium phosphate tribasic (10.8 g, 112.1 mmol) was added, after sufficient stirring, bis(triphenylphosphine)palladium (0.6 g, 1.1 mmol) was added. After 5 hours of reaction, the organic layer was filtered to remove the salt after cooling to room temperature, and the filtered organic layer was distilled. The obtained product was dissolved in 311 ml of chloroform (10 times the amount of the total volume of the product described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate, thereby obtaining a white solid compound 3 (21.4 g, 69%, MS: [M+H + = 832.1).

[0139] Synthesis Example 4: Synthesis of Compound 4

[0140]

[0141] 1) Synthesis of compound A-4

[0142] Under a nitrogen atmosphere, 2-chloro-4-(5'-chloro-[1,1':3',1"-terphenyl]-4-yl)-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (20 g, 36.7 mmol) and (phenyl-d5)boronic acid (4.7 g, 36.7 mmol) were added to 400 ml of toluene, stirred, and refluxed. Then, potassium carbonate (15.2 g) was added. A 110.2 mmol (1 g) compound was dissolved in 46 mL of water and added. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.6 g, 1.1 mmol) was added. After reacting for 7 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was dissolved in 1086 mL of tetrahydrofuran (equivalent to 50 times the total volume of the solid), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from tetrahydrofuran and ethyl acetate to give a white solid compound A-4 (11.1 g, 51%, MS: [M+H)). + =592.1).

[0143] 2) Synthesis of compound 4

[0144] Under a nitrogen atmosphere, compound A-4 (20 g, 33.8 mmol) and 9H-2,9'-bicarbazole (11.2 g, 33.8 mmol) were added to 400 mL of xylene, stirred, and refluxed. Then, tripotassium phosphate (9.8 g, 101.5 mmol) was added and stirred thoroughly, followed by bis(tri-tert-butylphosphine)palladium (0.5 g, 1 mmol). After reacting for 5 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was dissolved in 900 mL of chloroform (equivalent to 30 times the total volume of the solid), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to give a white solid, compound 4 (18.3 g, 61%, MS: [M+H)). + =888.1).

[0145] Synthesis Example 5: Synthesis of Compound 5

[0146]

[0147] 1) Synthesis of Compound A-5

[0148] Under a nitrogen atmosphere, 2-bromo-9H-carbazole (20 g, 81.3 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (9H-carbazole-1,2,3,4,5,6,7,8-d8) (14.2 g, 81.3 mmol) were added to 400 ml of xylene, stirred and refluxed. Then, potassium phosphate tribasic (23.4 g, 243.8 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (1.2 g, 2.4 mmol) was added. After 6 hours of reaction, the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. The obtained product was dissolved in 830 mL of toluene (30 times the amount of the total volume of the product described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with toluene and ethyl acetate, thereby obtaining a white solid compound A-5 (15.5 g, 56%, MS: [M+H + = 341.5).

[0149] 2) Synthesis of Compound 5

[0150] Under a nitrogen atmosphere, compound A-5 (15 g, 44.1 mmol) and 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (19.1 g, 44.1 mmol) were added to 150 ml of dimethylacetamide, stirred and refluxed. Then, potassium phosphate tribasic (28.1 g, 132.2 mmol) was added, and warmed and stirred. After 1 hour of reaction, it was cooled to room temperature, and the generated solid was filtered. The obtained solid was dissolved in 975 mL of chloroform (30 times the amount of the total volume of the solid described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate, thereby manufacturing a white solid compound 5 (24.4 g, 75%, MS: [M+H + = 738.9).

[0151] Synthesis Example 6: Synthesis of Compound 6

[0152]

[0153] 1) Synthesis of Compound A-6

[0154] Under a nitrogen atmosphere, 4-bromo-9H-carbazole (20 g, 81.3 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (14.2 g, 81.3 mmol) were added to 400 ml of xylene, stirred and refluxed. Then, potassium phosphate tribasic (23.4 g, 243.8 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (1.2 g, 2.4 mmol) was added. After 2 hours of reaction, it was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. The obtained product was dissolved in 830 mL of toluene (30 times the amount of the total volume of the product described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with toluene and ethyl acetate, thereby obtaining a white solid compound A-6 (16.3 g, 59%, MS: [M+H + = 341.5).

[0155] 2) Synthesis of Compound 6

[0156] Under a nitrogen atmosphere, compound A-6 (15 g, 44.1 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (15.8 g, 44.1 mmol) were added to 150 ml of dimethylacetamide, stirred and refluxed. Then, potassium phosphate tribasic (28.1 g, 132.2 mmol) was added, and warmed and stirred. After 3 hours of reaction, it was cooled to room temperature, and the generated solid was filtered. The solid obtained as a result was dissolved in 875 mL of chloroform (30 times the amount of the total volume of the solid described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate, thereby obtaining a white solid compound 6 (19 g, 65%, MS: [M+H + = 662.8).

[0157] Synthesis Example 7: Synthesis of Compound 7

[0158]

[0159] 1) Synthesis of Compound A-7

[0160] Under a nitrogen atmosphere, 4-bromo-9H-carbazole (20 g, 81.3 mmol) and 9H-carbazole (13.6 g, 81.3 mmol) were added to 400 ml of xylene, stirred and refluxed. Then, potassium phosphate tribasic (23.4 g, 243.8 mmol) was added, and after sufficient stirring, bis(tri-tert-butylphosphine)palladium (1.2 g, 2.4 mmol) was added. After 3 hours of reaction, it was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. The obtained product was dissolved in 810 mL of toluene (30 times the amount of the total volume of the product described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with toluene and ethyl acetate, thereby obtaining Compound A-7 (15.9 g, 59%, MS: [M+H + = 333.4).

[0161] 2) Synthesis of Compound B-2

[0162] Under a nitrogen atmosphere, Compound A-7 (15 g, 45.1 mmol) and 2-chloro-4-(3-chlorophenyl)-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (17.7 g, 45.1 mmol) were added to 150 ml of dimethylacetamide, stirred and refluxed. Then, potassium phosphate tribasic (28.7 g, 135.4 mmol) was added, and warmed and stirred. After 1 hour of reaction, it was cooled to room temperature, and the generated solid was filtered. The obtained solid was dissolved in 932 mL of chloroform (30 times the amount of the total volume of the solid described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate, thereby obtaining Compound B-2 (21.7 g, 70%, MS: [M+H + = 689.2).

[0163] 3) Synthesis of Compound 7

[0164] Under a nitrogen atmosphere, compound B-2 (15 g, 21.8 mmol) and (phenyl-d5)boronic acid (2.8 g, 21.8 mmol) were added to 300 ml of dioxin. In a dioxane, the mixture was stirred and refluxed. Then, tripotassium phosphate (13.9 g, 65.4 mmol) was dissolved in 14 mL of water and added to the solution. After thorough stirring, palladium (0.4 g, 0.7 mmol) and tricyclohexylphosphine (0.4 g, 1.3 mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid obtained as a result was dissolved in 481 mL of dichlorobenzene (DCB) (equivalent to 30 times the total volume of the solid), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound as a result was recrystallized from DCB and ethyl acetate to give a yellow solid compound 7 (9.8 g, 61%, MS: [M+H)). + =735.9).

[0165] Synthesis Example 8: Synthesis of Compound 8

[0166]

[0167] 1) Synthesis of compound A-8

[0168] Under a nitrogen atmosphere, 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5- triazine (20 g, 63.3 mmol) and 2-([1,1'-biphenyl]-3-yl-2',3',4',5',6'-d5)-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (18 g, 63.3 mmol) were added to 400 ml of toluene, stirred and refluxed. Then, potassium carbonate (26.2 g, 189.8 mmol) was dissolved in 79 ml of water and added, after being stirred well, bis(tri-t-butylphosphine)palladium (1 g, 1.9 mmol) was added. After 3 hours of reaction, the organic layer and the water layer were separated, and the organic layer was distilled. The obtained product was dissolved in 1388 ml of tetrahydrofuran (50 times the amount of the total volume of the product described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using tetrahydrofuran and ethyl acetate through a silica gel column, and as a result, a white solid compound A-8 (21.4 g, 77%, MS: [M+H + = 439.9) was obtained.

[0169] 2) Synthesis of Compound 8

[0170] Under a nitrogen atmosphere, compound A-8 (10 g, 22.8 mmol) and compound A-9 (7.7 g, 22.8 mmol) were added to 100 ml of dimethylacetamide, stirred and refluxed. Then, potassium phosphate tribasic (14.5 g, 68.3 mmol) was added, warmed and stirred. After 3 hours of reaction, it was cooled to room temperature, and the generated solid was filtered. The obtained solid was dissolved in 506 ml of chloroform (30 times the amount of the total volume of the solid described above), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound as a result was recrystallized with chloroform and ethyl acetate, and as a result, a white solid compound 8 (13.2 g, 78%, MS: [M+H + = 741.9) was obtained.

[0171] Example 1

[0172] ITO (Indium Tin Oxide) was coated as a thin film on a glass substrate having a thickness of The glass substrate on which ITO was coated as a thin film was washed with distilled water in which a detergent was dissolved, using ultrasonic waves. At this time, the detergent was a product of Fischer Co., and the distilled water was distilled water filtered twice using a filter manufactured by Millipore Co. The ITO was washed for 30 minutes, and then ultrasonic washing was repeated twice for 10 minutes using distilled water. After the washing with distilled water was completed, the substrate was washed with solvents such as isopropyl alcohol, acetone, and methanol using ultrasonic waves, and then dried, and then transferred to a plasma cleaning machine. In addition, the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporation machine.

[0173] On the thus prepared ITO transparent electrode, a HT-A compound and 5 wt% of PD were vacuum evaporated at a thickness of to form a hole injection layer, and on the hole injection layer, only the HT-A compound was evaporated at a thickness of to form a hole transport layer. On the hole transport layer, a HT-B compound was vacuum evaporated at a thickness of to form an electron suppression layer. Subsequently, the compound 1 manufactured in Synthesis Example 1 was mixed as a first host and the GH-A compound was mixed as a second host at a weight ratio of 40:60 to form a host, and in addition, 15 wt% of the GD compound based on the total weight of the host was used as a dopant, and vacuum evaporated at a thickness of on the electron suppression layer to form a light emitting layer. Subsequently, an ET-A compound was vacuum evaporated at a thickness of on the light emitting layer to form a hole blocking layer. Subsequently, an ET-B compound and a Liq compound were vacuum evaporated at a weight ratio of 2:1 on the hole blocking layer to form an electron transport layer at a thickness of On the electron transport layer, LiF and magnesium were vacuum evaporated at a weight ratio of 1:1 at a thickness of to form an electron injection layer. On the electron injection layer, magnesium and silver were evaporated at a weight ratio of 1:4 to form a cathode at a thickness of to manufacture an organic light emitting device.

[0174]

[0175] In the above process, the evaporation rate of the organic compound was maintained at the evaporation rate of magnesium and silver was maintained at and the vacuum degree was maintained at 1 x 10-7 ~5 x 10 -8 To.

[0176] Examples 2 to 8 and Comparative Examples 1 to 5

[0177] The organic light emitting devices of Examples 2 to 8 and Comparative Examples 1 to 5 were respectively produced by the same method as described above in Example 1 except that the compound described in Table 1 below was used as the first host when forming the light emitting layer. At this time, when a mixture of two compounds was used as the host, the weight ratio between the host compounds is indicated in parentheses.

[0178] The structures of the compounds used in Comparative Examples 1 to 5 are shown below.

[0179]

[0180] <Experimental Example: Evaluation of Device Characteristics>

[0181] The organic light emitting devices produced in Examples 1 to 8 and Comparative Examples 1 to 5 were taken out after heat treatment in an oven at 100°C for 30 minutes, and the voltage, efficiency and lifetime (T95) were measured by applying a current, and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm 2 2

[0182] [Table 1]

[0183] [Table 1

[0184]

[0185] As a result of the experiment, when the organic light emitting devices of Examples 1 to 8 containing the compound substituted with deuterium were compared with Comparative Examples 1 to 5, they showed the same level of low voltage and high efficiency, and also showed a significant improvement effect in the lifetime characteristics. In particular, when Example 1 was compared with Comparative Examples 1, 3 and 4, the improvement effect in the lifetime characteristics due to the deuterium substitution in the first host compound contained in the light emitting layer was more clear.

[0186] From the above results, it can be seen that when the compound of Chemical Formula 1 is used in the light emitting layer of an organic electroluminescent device, it shows a low driving voltage and excellent efficiency, and also enables further improvement in the lifetime characteristics.

[0187] [Explanation of Symbols]

[0188] 1: substrate 2: anode

[0189] ​​3: organic layer 4: cathode

[0190] 5: hole injection layer 6: hole transport layer

[0191] 7: electron inhibition layer 8: light emitting layer

[0192] 9: hole blocking layer 10: electron transport layer

[0193] 11: electron injection layer

Claims

1. A compound represented by the following chemical formula 1 or 2: Chemical Formula 1 Chemical formula 2 In the chemical formulas 1 and 2, X1 to X3 are each N. Y is either O or S. Ar is C 6-20 aryl, and said Ar is unsubstituted or substituted with 5 to 15 deuterium, L1 and L2 are each independently a single bond, a phenylene, a biphenylene, or a terphenylene. R1 and R2 are each independently either hydrogen or deuterium. m is an integer from 1 to 7. n is an integer from 1 to 8. The compound represented by the chemical formula 1 or 2 contains 4 to 20 deuterium atoms.

2. The compound of claim 1, wherein, Ar can be phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, phenanthrene, or triphenylene. The Ar was either unsubstituted or substituted with 5 to 13 deuterium atoms.

3. The compound of claim 1, wherein, L1 is a single bond, phenylene, biphenylene, or terphenylene, and L2 is a single bond; or L1 is a single bond, and L2 is a phenylene or biphenylene.

4. The compound of claim 1, wherein, Ar can be phenyl, biphenyl, terphenyl, or triphenylene. The Ar atoms are replaced by 5 to 13 deuterium atoms. R1 and R2 are both hydrogen.

5. The compound of claim 1, wherein, Ar can be phenyl, biphenyl, terphenyl, or triphenylene. The Ar was not replaced. At least one of R1 and R2 is deuterium, and the rest are hydrogen. m is an integer from 1 to 7, and n is an integer from 1 to 8. The compound represented by the chemical formula 1 or 2 contains 4 to 15 deuterium atoms.

6. The compound of claim 1, wherein, Ar can be phenyl, biphenyl, terphenyl, or triphenylene. The Ar atoms are replaced by 5 to 13 deuterium atoms. At least one of R1 and R2 is deuterium, and the rest are hydrogen. m is an integer from 1 to 7, and n is an integer from 1 to 8.

7. A compound that is selected from any one of the following groups:

8. An organic light emitting device, wherein, include: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to claim 1.

9. The organic light emitting device according to claim 8, wherein, The organic layer containing the compound is a light-emitting layer.

Images