Novel compounds and organic light-emitting devices comprising the same

Abstract

The present application provides a novel compound and an organic light emitting device using the same.

Description

TECHNICAL FIELD

[0001] Cross Reference to Related Applications

[0002] This application claims priority based on Korean Patent Application No. 10-2020-0057293 filed on May 13, 2020 and Korean Patent Application No. 10-2021-0061610 filed on May 12, 2021, the contents of which are incorporated herein in their entirety as part of the present specification.

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

[0004] Generally, an organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy by 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 a lot of studies are being conducted.

[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 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, a light emitting 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-trip 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] PRIOR ART DOCUMENT

[0008] PATENT DOCUMENT

[0009] (Patent Document 0001) Korean Patent Laid-open Publication No. 10-2013-073537 SUMMARY

[0010] TECHNICAL PROBLEM

[0011] The present application relates to a novel compound and an organic light emitting device comprising the same.

[0012] SOLUTION TO PROBLEM

[0013] The present application provides a compound represented by Chemical Formula 1 below:

[0014] [Chemical Formula 1]

[0015]

[0016] In the above Chemical Formula 1,

[0017] Y is O or S,

[0018] L is a single bond or a substituted or unsubstituted C 6-60 arylene group,

[0019] X1, X2, and X3 are each independently N or CH, but one or more of which is N,

[0020] Ar1is a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group containing one or more heteroatoms selected from the group consisting of N, O, and S,

[0021] Ar2and Ar3are each independently a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group containing one or more heteroatoms selected from the group consisting of N, O, and S,

[0022] R1and R2are each independently hydrogen; deuterium; a substituted or unsubstituted C 1-60 alkyl group; a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group containing one or more heteroatoms selected from the group consisting of N, O, and S,

[0023] m and n are each independently an integer of 0 to 4.

[0024] Further, 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, one or more of the organic layers comprising the compound of the present application.

[0025] Effects of the Invention

[0026] The compound represented by the above Chemical Formula 1 can be used as a material for an organic layer of an organic light emitting device, and can achieve an improvement in efficiency, a low driving voltage, and / or an improvement in lifetime characteristics in the organic light emitting device. In particular, the compound represented by the above Chemical Formula 1 can be used as a material for a hole blocking layer, an electron transporting layer, or a light emitting layer. BRIEF DESCRIPTION OF DRAWINGS

[0027] Figure 1 An example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 4, and a cathode 3 is illustrated.

[0028] Figure 2 An example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 9, an electron suppression layer 10, a light emitting layer 4, a hole blocking layer 5, an electron injection layer 6 and an electron transport layer 7, and a cathode 3 is illustrated. DETAILED DESCRIPTION

[0029] Hereinafter, a more detailed description will be given in order to help understanding of the present application.

[0030] (Explanation of Terms)

[0031] In the present specification, represents a bond to another substituent.

[0032] In the present specification, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium (D); a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; an oxidized phosphine group; an alkoxy group; an aryloxy group; an alkylthio group arylthio group alkylsulfonyl group arylsulfonyl group silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamino group; aralkylamino group; heteroaralkylamino group; arylamino group; arylphosphine group; or one or more substituents selected from a heterocyclic group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents from the above exemplified substituents. For example, "a substituent connected with two or more substituents" can be biphenyl. That is, biphenyl can be an aryl group, or can be interpreted as a substituent connected with two phenyl groups.

[0033] In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, it can be a group of the following structure, but is not limited thereto.

[0034]

[0035] 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, it can be a group of the following structural formula, but is not limited thereto.

[0036]

[0037] In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, it can be a group of the following structure, but is not limited thereto.

[0038]

[0039] In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a tert-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.

[0040] In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a tert-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

[0041] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

[0042] In the present specification, the above-mentioned alkyl group can be straight-chained 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. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, an n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, an n-nonyl group, a 2,2-dimethylheptyl group, a 1-ethyl-propyl group, a 1,1-dimethyl-propyl group, an isohexyl group, a 4-methylhexyl group, a 5-methylhexyl group, and the like, but is not limited thereto.

[0043] In the present specification, the above-mentioned alkenyl group can be straight-chained 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. Specific examples include an ethenyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylethen-1-yl group, a 2-phenylethen-1-yl group, a 2,2-diphenylethen-1-yl group, a 2-phenyl-2-(naphth-1-yl)ethen-1-yl group, a 2,2-bis(diphen-1-yl)ethen-1-yl group, a stilbenyl group, a styryl group, and the like, but is not limited thereto.

[0044] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but not limited thereto.

[0045] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and can 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. As the monocyclic aryl group, there are phenyl, biphenyl, terphenyl, and the like, but not limited thereto. As the polycyclic aryl group, there are naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and can 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. As the monocyclic aryl group, there are phenyl, biphenyl, terphenyl, and the like, but not limited thereto. As the polycyclic aryl group, there are naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,

[0046] In the present specification, the fluorenyl group can be substituted, and two substituents can be combined with each other to form a spiro structure. In the case where the fluorenyl group is substituted, there are In the present specification, the fluorenyl group can be substituted, and two substituents can be combined with each other to form a spiro structure. In the case where the fluorenyl group is substituted, there are

[0047] In the present specification, the heteroaryl group is a heterocyclic group having aromaticity, which contains one or more of O, N, Si, and S as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. As examples of the heteroaryl group, there are thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, thiazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthroline, isoindolyl, indazolyl, indolizinyl, purinyl, naphthyridinyl, pteridinyl, phenarsenyl, phenazinyl, and dibenzofuranyl, but not limited thereto. thiazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthroline, isoindolyl, indazolyl, indolizinyl, purinyl, naphthyridinyl, pteridinyl, phenarsenyl, phenazinyl, and dibenzofuranyl, but not limited thereto.

[0048] In the present specification, the aryl group in aralkyl group, aralkenyl group, alkylaryl group, arylamine 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 can apply the description of the heterocyclic 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 apply. In the present specification, the heteroarylene group is a 2-valent group, and in addition thereto, the description of the heterocyclic group described above can apply. 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 apply. In the present specification, the heterocyclic 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 heterocyclic group described above can apply.

[0049] (Compound)

[0050] The present application provides a compound represented by Chemical Formula 1:

[0051] [Chemical Formula 1]

[0052]

[0053] In the above Chemical Formula 1, the triazine-based substituent is linked to any one of carbons selected from 1, 2, 3, 4, 5, 6, 7, and 8 in the above Chemical Formula 1, and R1and R2, each independently, can be linked to other carbons not substituted with the triazine-based substituent.

[0054] Y is O or S,

[0055] L is a single bond or a substituted or unsubstituted C 6-60 arylene group,

[0056] X1, X2, and X3, each independently, are N or CH, but one or more of them are N,

[0057] Ar1is a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group,

[0058] Ar2and Ar3, each independently, are a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group,

[0059] R1and R2, each independently, are hydrogen; deuterium; a substituted or unsubstituted C 1-60alkyl; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C 2-60 heteroaryl,

[0060] m and n are each independently an integer of 0 to 4.

[0061] Preferably, the compound represented by Chemical Formula 1 above is a compound represented by Chemical Formulas 1-1 to 1-8 below:

[0062] [Chemical Formula 1-1]

[0063]

[0064] [Chemical Formula 1-2]

[0065]

[0066] [Chemical Formula 1-3]

[0067]

[0068] [Chemical Formula 1-4]

[0069]

[0070] [Chemical Formula 1-5]

[0071]

[0072] [Chemical Formula 1-6]

[0073]

[0074] [Chemical Formula 1-7]

[0075]

[0076] [Chemical Formula 1-8]

[0077]

[0078] In the above Chemical Formulas 1-1 to 1-8,

[0079] Y, L, X1, X2, X3, Ar1, Ar2, Ar3, R1, R2, m, and n are the same as defined above,

[0080] m' and n' are each independently an integer of 0 to 3.

[0081] Preferably, L is a single bond, phenylene, biphenylene, or naphthylene.

[0082] Preferably, Ar1is phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthryl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, or dibenzothiophenyl, each of which is independently substituted with at least one or more deuterium or unsubstituted. When Ar1is substituted with deuterium, preferably, it is substituted with 4 or more deuterium.

[0083] Preferably, Ar2and Ar3are each independently phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, or dibenzothiophenyl. More preferably, phenyl, biphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, dibenzofuranyl, or dibenzothiophenyl.

[0084] Preferably, R1and R2are each independently hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, or dibenzothiophenyl. More preferably, hydrogen, deuterium, or phenyl.

[0085] Preferably, m and n are each independently an integer of 0 to 3. More preferably, m and n are each independently 0 or 1.

[0086] Preferably, the compound represented by Chemical Formula 1 above is any one selected from the following compounds:

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115] The compound represented by Chemical Formula 1 according to the present invention includes a phenanthro oxazole and a phenanthrothiazole compound nuclear structure, and these structures have the characteristics of large electronegativity and rich electrons at the same time. Moreover, the present invention has a structure formed by fusing groups such as phenanthrene and oxazole, or phenanthrene and thiazole, and has a rigid characteristic, so that charge transfer between molecules is easy. In particular, a triazine-based substituent as a nitrogen-containing heterocycle is further connected here, so the electron transport ability is excellent. Through such excellent intermolecular stacking and charge transport ability, fast electron current characteristics can be achieved.

[0116] Therefore, when the compound according to the present invention is applied to the electron transport layer, hole blocking layer, and n-type host of the light-emitting layer, which mainly transport electrons in an organic electroluminescent device, it can make a great contribution to low-voltage driving, improvement of efficiency and lifespan. The improvement of such device characteristics is suitable for ensuring stability and improving performance when exposed to high temperature in the panel manufacturing process.

[0117] The compound represented by Chemical Formula 1 above can be manufactured by Reaction Formula 1 below.

[0118] [Reaction Formula 1]

[0119]

[0120] In Reaction Formula 1 above, the definition of the substituent other than X is the same as described above, and X is halogen, preferably bromine or chlorine.

[0121] Reaction Formula 1 above is a Suzuki coupling reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reaction group used for the Suzuki coupling reaction can be changed according to the technique known in the art.

[0122] In the compound represented by Chemical Formula 1 above, the position of each substituent can be manufactured by referring to Reaction Formula 1 above and by appropriately changing the structure of the starting material. The manufacturing method of such a compound represented by Chemical Formula 1 above can be more specifically described in the Manufacturing Examples described later.

[0123] (Organic Light Emitting Device)

[0124] In addition, the present application provides an organic light emitting device including the compound represented by Chemical Formula 1 above. 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, wherein one or more of the organic layers include the compound represented by Chemical Formula 1 above.

[0125] The organic layer of the organic light emitting device of the present application can include, in addition to the compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2 below:

[0126] [Chemical Formula 2]

[0127]

[0128] In Chemical Formula 2 above,

[0129] A is a phenyl ring,

[0130] B is a naphthalene ring,

[0131] Ar'1is a substituted or unsubstituted C 6-60 aryl group; or a substituted or unsubstituted C 2-60 heteroaryl group,

[0132] Ar'2and Ar'3are each independently a substituted or unsubstituted C 6-60an aryl group; or a substituted or unsubstituted C 2-60 heteroaryl,

[0133] R'1and R'2are each independently hydrogen; deuterium; a substituted or unsubstituted C 6-60 an aryl group; or a substituted or unsubstituted C 2-60 heteroaryl

[0134] a is an integer of 0 to 4,

[0135] b is an integer of 0 to 6.

[0136] Preferably, the compound represented by the above Chemical Formula 2 is represented by the following Chemical Formulas 2-1 to 2-3.

[0137] [Chemical Formula 2-1]

[0138]

[0139] [Chemical Formula 2-2]

[0140]

[0141] [Chemical Formula 2-3]

[0142]

[0143] In the above Chemical Formulas 2-1 to 2-3,

[0144] Ar'1, Ar'2, Ar'3, R'1, R'2, a, and b are the same as defined above.

[0145] Preferably, Ar'1is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a naphthylphenyl group, a phenylnaphthyl group, a phenanthryl group, a triphenylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group. More preferably, it is a phenyl group, a biphenyl group, a naphthyl group, a naphthylphenyl group, or a phenylnaphthyl group.

[0146] Preferably, Ar'2and Ar'3are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a naphthylphenyl group, a phenylnaphthyl group, a phenanthryl group, a triphenylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group. More preferably, it is a phenyl group, a biphenyl group, a naphthyl group, a naphthylphenyl group, a phenylnaphthyl group, a dimethylfluorenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0147] Preferably, R'1and R'2are each independently hydrogen, deuterium, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophenyl group. More preferably, it is hydrogen or deuterium.

[0148] Preferably, a and b are each an independent integer from 0 to 2.

[0149] Preferably, the compound represented by the above chemical formula 2 is selected from any one of the following compounds:

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196] The organic layer of the organic light emitting device according to the present application can be formed of a single layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light emitting device according to the present application can have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as the organic layer. However, the structure of the organic light emitting device is not limited thereto and can include a smaller number of organic layers.

[0197] In addition, the organic layer can include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, the hole transport layer, or the layer that simultaneously performs hole injection and transport can include the compound represented by Chemical Formula 1.

[0198] In addition, the organic layer can include a light emitting layer, and the light emitting layer can include the compound represented by Chemical Formula 1. Preferably, the light emitting layer can further include the compound represented by Chemical Formula 2 together with the compound represented by Chemical Formula 1. The two compounds are combined to be used as a host compound, and are suitable for an organic light emitting device, and are suitable for achieving low voltage, high efficiency, and long lifespan characteristics.

[0199] In addition, the organic layer can include a hole blocking layer, and the hole blocking layer can include the compound represented by Chemical Formula 1.

[0200] In addition, the organic light emitting device according to the present application can be an organic light emitting device in which the first electrode is an anode and the second electrode is a cathode, and the anode, one or more organic layers, and the cathode are sequentially stacked on a substrate (normal type). In addition, the organic light emitting device according to the present application can be an organic light emitting device in which the first electrode is a cathode and the second electrode is an anode, and the cathode, one or more organic layers, and the anode are sequentially stacked on a substrate (inverted type). For example, the structure of the organic light emitting device according to an embodiment of the present application is illustrated in FIG. 1. Figure 1 and 2 .

[0201] Figure 1 FIG. 1 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 4, and a cathode 3. In the structure as described above, the compound represented by Chemical Formula 1 can be included in the light emitting layer. Preferably, the light emitting layer can further include the compound represented by Chemical Formula 2.

[0202] Figure 2An example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 9, an electron suppression layer 10, a light emitting layer 4, a hole blocking layer 5, an electron injection layer 6 and an electron transport layer 7, and a cathode 3 is illustrated. In the structure as described above, the compound represented by the above chemical formula 1 can be contained in the above light emitting layer or hole blocking layer.

[0203] 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 the above chemical formula 1 is contained in one or more of the above organic layers. Further, when the above organic light emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

[0204] For example, the organic light emitting device according to the present application can be manufactured by sequentially stacking a first electrode, an organic layer and a second electrode 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 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 substance usable as a cathode on the organic layer. In addition to this method, an organic light emitting device can be manufactured by sequentially evaporating a cathode substance, an organic layer and an anode substance on a substrate.

[0205] In addition, the compound represented by the above chemical formula 1 can be used to form an organic layer by a solution coating method as well as a vacuum evaporation method 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.

[0206] In addition, an organic light emitting device can be manufactured by sequentially evaporating a cathode substance, an organic layer and an anode substance on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited thereto.

[0207] 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.

[0208] As the anode material, a material having a large work function is preferable in order to easily inject holes into the organic layer. Examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, and the like, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and the like; combinations of a metal and an oxide such as ZnO:Al or SnO2:Sb, and the like; electrically conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.

[0209] As the cathode material, a material having a small work function is preferable in order to easily inject electrons into the organic layer. Examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered structure materials such as LiF / Al or LiO2 / Al, and the like, but are not limited thereto.

[0210] 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, having an effect of injecting holes from the anode, having an excellent hole injection effect to the light emitting layer or the light emitting material, preventing excitons generated in the light emitting layer from migrating to the electron injection layer or the electron injection material, and having an excellent film formation capability is preferable. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexacyno hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, and electrically conductive polymers such as polyaniline and polythiophene, but are not limited thereto.

[0211] 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 material is a material that can receive holes from the anode or the hole injection layer and transport them to the light emitting layer, and a material having a large mobility of holes is suitable. The hole transport material uses a compound represented by Chemical Formula 1, or can use arylamine-based organic material, electrically conductive polymer, and block copolymer having both a conjugated portion and a non-conjugated portion, but is not limited thereto.

[0212] The aforementioned electron suppression layer (or electron blocking layer, electron blocking layer) refers to a layer formed on the aforementioned hole transport layer, preferably disposed in contact with the light-emitting layer, which adjusts the hole mobility, prevents excessive electron migration, and increases the probability of hole-electron binding, thereby improving the efficiency of the organic light-emitting device. The aforementioned electron suppression layer contains an electron blocking material, such as aryl amine-based organic compounds, but is not limited to this.

[0213] The aforementioned luminescent materials are those capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region. Preferably, these materials possess high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3), carbazole compounds, and dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0214] The aforementioned luminescent layer can comprise a host material and a dopant material, as described above. The host material can be a compound of Formula 1, and preferably, it can be used together with a compound of Formula 2. Furthermore, the host material can also comprise aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0215] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, etc. Diindrone pyrene, etc., styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0216] The aforementioned hole-blocking layer refers to a layer formed on the light-emitting layer, preferably in contact with it, that regulates electron mobility, prevents excessive hole migration, and increases the probability of hole-electron binding, thereby improving the efficiency of the organic light-emitting layer device. The aforementioned hole-blocking layer contains a hole-blocking material, such as a compound of the aforementioned chemical formula 1. Other examples of usable hole-blocking materials include azazine derivatives, triazole derivatives, etc. Compounds containing electron-withdrawing groups, such as diazole derivatives, phenanthrene-rhein derivatives, and phosphine oxide derivatives, are included, but are not limited to these.

[0217] The aforementioned electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, simultaneously functioning as an electron transport layer and an electron injection layer. It is formed on the aforementioned light-emitting layer or the aforementioned hole-blocking layer. Such an electron injection and transport material is suitable because it can effectively receive electrons from the cathode and transfer them to the light-emitting layer, and materials with high electron mobility are preferred. Specific examples of electron injection and transport materials include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can be combined with fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, or nitrogen-containing five-membered ring derivatives may be used together, but are not limited to these.

[0218] The aforementioned electron injection and transport layers can also be formed as separate layers, such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the aforementioned light-emitting layer or the aforementioned hole-blocking layer, and the aforementioned electron injection and transport materials can be used as the electron transport material contained in the aforementioned electron transport layer. Alternatively, the electron injection layer is formed on the aforementioned electron transport layer, and LiF, NaCl, CsF, Li₂O, BaO, fluorenone, anthraquinone dimethane, biphenylquinone, thiamethoxam dioxide, etc., can be used as the electron injection material contained in the aforementioned electron injection layer. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc.

[0219] As the above 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]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), gallium bis(2-methyl-8-quinolate) chloride, gallium bis(2-methyl-8-quinolate)(o-cresol), aluminum bis(2-methyl-8-quinolate)(1-naphthol), gallium bis(2-methyl-8-quinolate)(2-naphthol), etc., but are not limited thereto.

[0220] 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.

[0221] In addition, the compound represented by the above Chemical Formula 1 can be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.

[0222] The compound represented by the above Chemical Formula 1 and the organic light emitting device including the same will be specifically described in the following Examples. However, the following Examples are for exemplifying the present application, and the scope of the present application is not limited thereto.

[0223] [Manufacture Example]

[0224] Manufacture Example 1: Synthesis of Compound 1

[0225] Step 1) Synthesis of Compound 1-1

[0226]

[0227] Under a nitrogen atmosphere, 5-bromo-2-phenylphenanthro[9,10-d]oxazole (15.0 g, 40.1 mmol) and bis(pinacolato)diboron (11.2 g, 44.1 mmol) were dissolved in 300 ml of 1,4-dioxane, and then potassium acetate (8.9 g, 88.9 mmol) was added thereto. The mixture was stirred at 90°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and then filtered. The filtrate was concentrated under reduced pressure, and then purified by column chromatography to obtain Compound 1-1 (12.0 g, 80%). Oxazole (15.0 g, 40.1 mmol) and bis(pinacolato)diboron (11.2 g, 44.1 mmol) were dissolved in 300 ml of 1,4-dioxane, and then potassium acetate (8.9 g, 88.9 mmol) was added thereto. The mixture was stirred at 90°C for 3 hours. After the reaction was completed, the mixture was cooled to room temperature, and then filtered. The filtrate was concentrated under reduced pressure, and then purified by column chromatography to obtain Compound 1-1 (12.0 g, 80%). Alkane (1,4-dioxane) was stirred while refluxing. Then, potassium acetate (5.9 g, 60.1 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium(0) (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol) were added. The reaction was performed for 10 hours, and after cooling to room temperature, the organic layer was separated using chloroform and water, and then the organic layer was distilled. The compound was dissolved again in chloroform, washed with water twice, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica gel column chromatography, thereby producing 12.0 g of compound 1-1. (Yield 71%, MS: [M+H] + = 422)

[0228] Step 2) Synthesis of compound 1

[0229]

[0230] Compound 1-1 (15.0 g, 35.6 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (13.5 g, 39.2 mmol) were added to 300 ml of THF, stirred, and refluxed under a nitrogen atmosphere. Then, potassium carbonate (19.7 g, 142.4 mmol) was dissolved in 59 ml of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.1 mmol) was added. The reaction was performed for 12 hours, and after cooling to room temperature, the organic layer and the aqueous layer were separated, and then the organic layer was distilled. The compound was dissolved again in chloroform, washed with water twice, and then the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified using a silica gel column chromatography, and then purified by sublimation, thereby producing 7.5 g of compound 1. (Yield 35%, MS: [M+H] + = 604)

[0231] Preparation Example 2: Synthesis of compound 2

[0232]

[0233] In Production Example 1, 2-([l,l'-biphenyl]-4-yl)-4-chloro-6-phenyl-l,3,5-triazine was changed to 2-chloro-4-(dibenzo[b,d]furan-l-yl)-6-phenyl-l,3,5-triazine and used, and otherwise, Compound 2 was produced by the same production method as the production method of Compound 1. (MS: [M+H] + = 618)

[0234] Production Example 3: Synthesis of Compound 3

[0235]

[0236] Under a nitrogen atmosphere, 5-bromo-2-phenylphenanthrene[9,10-d] azepine (15.0 g, 40.1 mmol) and 2,4-di(naphthalen-2-yl)-6-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-l,3,5-triazine (23.6 g, 44.1 mmol) were added to 300 ml of THF, stirred and refluxed. Then, potassium carbonate (22.2 g, 160.3 mmol) was dissolved in 66 ml of water and added, after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.4 g, 1.2 mmol) was added. After 10 hours of reaction, it was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again dissolved in chloroform, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. After the concentrated compound was purified by silica gel column chromatography, 13.8 g of Compound 3 was produced by sublimation purification. (Yield 49%, MS: [M+H] + = 704)

[0237] Production Example 4: Synthesis of Compound 4

[0238]

[0239] In Production Example 3, 2,4-bis(naphthalen-2-yl)-6-(4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was changed to 2-(4-(naphthalen-2- yl)phenyl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)- 1,3,5-triazine, and Compound 4 was produced by the same production method as that of Compound 3, except for this.(MS: [M+H] + = 703)

[0240] Production Example 5: Synthesis of Compound 5

[0241]

[0242] In Production Example 1, 5-bromo-2-phenylphenanthro[9,10-d] oxazole was changed to 6-bromo-2-phenylphenanthro[9,10-d] oxazole, 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was changed to 2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine, and Compound 5 was produced by the same production method as that of Compound 1, except for this.(MS: [M+H] + = 578)

[0243] Production Example 6: Synthesis of Compound 6

[0244]

[0245] In Production Example 1, 5-bromo-2-phenylphenanthro[9,10-d] oxazole was changed to 6-bromo-2-phenylphenanthro[9,10-d] Compound 6 was prepared by replacing 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine with 2-chloro-4-(dibenzo[b,d]thiophen-4-yl)-6-(naphthalen-1-yl)-1,3,5-triazine, and otherwise prepared by the same method as compound 1. (MS:[M+H) + =684)

[0246] Manufacturing Example 7: Synthesis of Compound 7

[0247]

[0248] In manufacturing example 3, 5-bromo-2-phenylphenanthrene[9,10-d] was used. The azole was changed to 6-bromo-2-phenylphenanthrene[9,10-d]. Compound 7 was prepared by replacing 2,4-di(naphthalen-2-yl)-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)phenyl)-1,3,5-triazine with 2-(4-(naphthalen-1-yl)phenyl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)phenyl)-1,3,5-triazine(2-(4-(naphthalen-1-yl)phenyl)-4-phenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)phenyl)-1,3,5-triazine) using the same method as compound 3. (MS:[M+H) + =730)

[0249] Manufacturing Example 8: Synthesis of Compound 8

[0250]

[0251] In manufacturing example 3, 5-bromo-2-phenylphenanthrene[9,10-d] was used. The azole was changed to 6-bromo-2-phenylphenanthrene[9,10-d]. Instead of 2,4-di(naphthalen-2-yl)-6-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)-l,3,5-triazine, 2,4-di(naphthalen-2-yl)-6-(3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)phenyl)-l,3,5-triazine was used, and Compound 8 was produced by the same production method as that of Compound 1, except for this. (MS: [M+H] + = 704)

[0252] Production Example 9: Synthesis of Compound 9

[0253] Step 1) Synthesis of Compound 9-1

[0254]

[0255] Under a nitrogen atmosphere, 5,10-dibromo-2-phenylphenanthro[9,10-d] Oxazole (15.0 g, 33.1 mmol) and 2-(naphthalen-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)phenyl)-l,3,5-triazine (17.7 g, 36.4 mmol) were added to 300 ml of THF, stirred and refluxed. Then, potassium carbonate (18.3 g, 132.4 mmol) was dissolved in 55 ml of water and added, after sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (1.1 g, 1.0 mmol) was added. After 10 hours of reaction, it was cooled to normal temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was dissolved again in chloroform, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, thereby producing 18.9 g of Compound 9-1. (Yield 78%, MS: [M+H] + = 733)

[0256] Step 2) Synthesis of Compound 9

[0257]

[0258] Under a nitrogen atmosphere, compound 9-1 (15.0 g, 20.5 mmol) and phenylboronic acid (2.7 g, 22.6 mmol) were added to 300 mL of THF, stirred, and refluxed. Then, potassium carbonate (11.3 g, 82.0 mmol) was dissolved in 34 mL of water and added, and after thorough stirring, tetrakis(triphenylphosphine)palladium(0) (0.7 g, 0.6 mmol) was added. After reacting for 12 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then purified by sublimation to produce 7.2 g of compound 9. (Yield 48%, MS: [M+H)) + =730)

[0259] Manufacturing Example 10: Synthesis of Compound 10

[0260]

[0261] In manufacturing example 9, 5,10-dibromo-2-phenylphenanthrene[9,10-d] was used. The azole was changed to 6,9-dibromo-2-phenylphenanthrene[9,10-d]. Compound 10 was prepared by using 6,9-dibromo-2-phenylphenanthro[9,10-d]oxazole, with 2-(naphthalen-2-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine replaced by 2-(naphthalen-1-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (2-(naphthalen-1-yl)-4-phenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine), except that the same method as that used for preparing compound 1 was employed. (MS:[M+H) + =730)

[0262] Manufacturing Example 11: Synthesis of Compound 11

[0263]

[0264] In manufacturing example 1, 5-bromo-2-phenylphenanthrene[9,10-d] was used. Compound 11 was used by replacing azole with 5-bromo-2-(naphthalen-2-yl)phenanthro[9,10-d]thiazole and replacing 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine with 2-chloro-4,6-diphenyl-1,3,5-triazine. Otherwise, compound 11 was prepared by the same method as compound 1. (MS:[M+H) + =594)

[0265] [Experimental Example 1 - Applicable to Hole-Blocking Layers]

[0266] [Examples and Comparative Examples]

[0267] Comparative Example 1-1

[0268] ITO (Indium Tin Oxide) is used in... A glass substrate with a thickness of [insert thickness here] coated into a thin film is immersed in distilled water containing detergent and washed using ultrasound. The detergent used is Decon [insert detergent name here]. TM For the CON705 substrate, distilled water was used that had been filtered twice using a 0.22μm sterilizing filter from Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for a total of 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed for 10 minutes each with isopropanol, acetone, and methanol, respectively, and then dried before being transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0269] On the prepared ITO transparent electrode, HI-A and LG-101 are sequentially applied respectively... A hole injection layer is formed by thermal vacuum evaporation of a material to a certain thickness. As a hole transport layer, the following HT-A is used... After vacuum evaporation to a thickness of [thickness], it serves as an electron blocking layer, upon which the following EB-A is applied. The thickness was achieved through thermal vacuum evaporation. Next, as the light-emitting layer, BH-A and BD-A were deposited at a weight ratio of 96:4. Vacuum evaporation was performed to a thickness of [amount missing]. Next, HB-A was deposited as a hole-blocking layer. a thickness of 100 A as an electron transport layer, and a compound represented by ET-A and Liq at a weight ratio of 1:1 and at a thickness of 100 A as a hole blocking layer, and then, a compound represented by Liq at a thickness of 100 A as an electron injection layer, thereby fabricating an organic light emitting device. a thickness of 100 A as an electron transport layer, and a compound represented by ET-A and Liq at a weight ratio of 1:1 and at a thickness of 100 A as a hole blocking layer, and then, a compound represented by Liq at a thickness of 100 A as an electron injection layer, thereby fabricating an organic light emitting device. a thickness of 100 A as an electron transport layer, and a compound represented by ET-A and Liq at a weight ratio of 1:1 and at a thickness of 100 A as a hole blocking layer, and then, a compound represented by Liq at a thickness of 100 A as an electron injection layer, thereby fabricating an organic light emitting device. a thickness of 100 A as an electron transport layer, and a compound represented by ET-A and Liq at a weight ratio of 1:1 and at a thickness of 100 A as a hole blocking layer, and then, a compound represented by Liq at a thickness of 100 A as an electron injection layer, thereby fabricating an organic light emitting device. a thickness of 100 A as an electron transport layer, and a compound represented by ET-A and Liq at a weight ratio of 1:1 and at a thickness of 100 A as a hole blocking layer, and then, a compound represented by Liq at a thickness of 100 A as an electron injection layer, thereby fabricating an organic light emitting device.

[0270]

[0271] Examples 1-1 to 1-11 and Comparative Examples 1-1 to 1-7

[0272] In the above Comparative Example 1-1, as a material for a hole blocking layer, the compounds described in Table 1 were used, and otherwise, the organic light emitting devices of Examples 1-1 to 1-11 and Comparative Examples 1-2 to 1-7 were respectively fabricated by using the same method as Comparative Example 1-1.

[0273]

[0274] The organic light emitting devices fabricated in the above Examples 1-1 to 1-11 and Comparative Examples 1-1 to 1-7 were applied with a current, and voltage, efficiency, and lifetime (T95) were measured, and the results thereof are shown in Table 1 below. Here, the voltage and efficiency were measured by applying a current density of 10 mA / cm 2 2

[0275] [Table 1]

[0276]

[0277] From the results of the above Table 1, it can be known that when a compound having a structure of Formula 1 is used as a hole blocking layer compound for an organic light emitting device, a device having low voltage, high efficiency, and long lifetime characteristics can be obtained.

[0278] [Experimental Example 2 - Applicable to Emission Layer]

[0279] [Examples and Comparative Examples]

[0280] Comparative Example 2-1

[0281] ITO (indium tin oxide) was deposited to a thickness of 1500 A as an anode, and a compound represented by ET-A and Liq at a weight ratio of 1:1 and at a thickness of 100 A as an electron transport layer, and a compound represented by ET-A and Liq at a weight ratio of 1:1 and at a thickness of 100 A as a hole blocking layer, and then, a compound represented by Liq at a thickness of 100 A as an electron injection layer, thereby fabricating an organic light emitting device. ​​The glass substrate of which the thickness was coated into a thin film was put into distilled water in which a detergent was dissolved, and washed using ultrasonic waves. At this time, the detergent was Decon 90 manufactured by Fisher Scientific Company. TM The CON705 product, and distilled water used distilled water filtered twice using a 0.22 μm sterilizing filter manufactured by Millipore Corporation. After the ITO was washed for 30 minutes, ultrasonic washing was performed for 10 minutes using distilled water twice. After the distilled water washing was completed, ultrasonic washing was performed for 10 minutes using solvents of isopropyl alcohol, acetone, and methanol, respectively, and dried, and then transferred to a plasma cleaning machine. Further, the above substrate was cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum evaporation machine.

[0282] On the ITO transparent electrode thus prepared, HI-A and LG-101 were sequentially vacuum evaporated at a thickness of 50 nm and 20 nm, respectively, to form a hole injection layer. On the hole injection layer, HT-A was vacuum evaporated at a thickness of 50 nm as a hole transport layer, and EB-A was hot vacuum evaporated at a thickness of 10 nm as an electron blocking layer. RH-A and RD-A were vacuum evaporated at a weight ratio of 98:2 and a thickness of 20 nm and 2 nm, respectively, as a light emitting layer. ET-B and Liq were hot vacuum evaporated at a ratio of 1:1 and a thickness of 20 nm and 20 nm, respectively, as an electron transport and injection layer, and then Liq was vacuum evaporated at a thickness of 20 nm.

[0283]

[0284] On the electron injection layer, magnesium and silver were evaporated at a ratio of 10:1 and a thickness of 100 nm and 10 nm, respectively, aluminum was evaporated at a thickness of 200 nm to form a cathode, thereby producing an organic light emitting device. Examples 2-1 to 2-11 and Comparative Examples 2-2 and 2-7

[0285] As the material of the light emitting layer of the above Comparative Example 2-1, the components of Table 2 were used instead of RH-A and RD-A, and otherwise, the organic light emitting devices of Examples 2-1 to 2-11 and Comparative Examples 2-2 to 2-7 were produced using the same method as Comparative Example 2-1. At this time, when a mixture of two compounds was used as the host, the weight ratio between the host compounds is indicated in the parentheses.

[0286]

[0287]

[0288] Experimental Example 2​​​​​​​

[0289] The organic light emitting devices prepared in Examples 2-1 to 2-11 and Comparative Examples 2-1 to 2-7 above were applied with current, and voltage, efficiency, lifetime were measured, and the results are shown in Table 2 below. At this time, voltage, efficiency were measured at the time of applying current density of 10 mA / cm 2 2 LT97 means the time when the initial luminance is reduced to 97% at current density of 20 mA / cm

[0290] [Table 2]

[0291]

[0292] From the results of Table 2 above, it can be known that when the compound having the structure of Chemical Formula 1 is used as a host compound of the light emitting layer of the organic light emitting device, a device having low voltage, high efficiency, long lifetime characteristics can be obtained.

[0293] Explanation of Symbols

[0294] 1: Substrate 2: Anode

[0295] 3: Cathode 4: Light Emitting Layer

[0296] 5: Hole Blocking Layer 6: Electron Injection Layer

[0297] 7: Electron Transport Layer 8: Hole Injection Layer

[0298] 9: Hole Transport Layer 10: Electron Suppression Layer​

Claims

1. A compound represented by the following chemical formula 1: Chemical Formula 1 In the chemical formula 1, Y is either O or S. L is a single bond or C is either substituted with one or more deuterium atoms or is unsubstituted. 6-60 Alpha-aryl X1, X2, and X3 are N, Ar1 can be phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrene, triphenylene, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, or dibenzothiopheneyl. The Ar1 is either substituted with one or more deuterium atoms or not substituted. Ar2 and Ar3 are each independently phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, phenylnaphthyl, phenanthrene, triphenylene, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, or dibenzothiopheneyl. R1 is hydrogen, deuterium, or a phenyl group substituted with or unsubstituted with one or more deuterium groups. R2 is a phenyl group that is substituted or unsubstituted with one or more deuterium groups, a biphenyl group that is substituted or unsubstituted with one or more deuterium groups, a terphenyl group that is substituted or unsubstituted with one or more deuterium groups, a naphthyl group that is substituted or unsubstituted with one or more deuterium groups, a dibenzofuranyl group that is substituted or unsubstituted with one or more deuterium groups, or a dibenzothiophenyl group that is substituted or unsubstituted with one or more deuterium groups. m and n are each an independent integer from 0 to 4.

2. The compound according to claim 1, wherein, Compounds represented by chemical formula 1 are represented by the following chemical formulas 1-1 to 1-8: Chemical Formula 1-1 Chemical formula 1-2 Chemical formulas 1-3 Chemical formulas 1-4 Chemical formulas 1-5 Chemical formulas 1-6 Chemical formulas 1-7 Chemical formulas 1-8 In the chemical formulas 1-1 to 1-8, Y, L, X1, X2, X3, Ar1, Ar2, Ar3, R1, R2, m, and n are the same as defined in claim 1. m' and n' are each independent integers from 0 to 3.

3. The compound according to claim 1, wherein, L can be a single bond, phenylene, biphenylene, or naphthylene.

4. The compound according to claim 1, wherein, m and n are each independently 0 or 1.

5. The compound according to claim 1, wherein, The compound represented by the chemical formula 1 is selected from any one of the following compounds:

6. 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 any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, wherein, The organic layer containing the compound is a hole-blocking layer or an electron transport layer.

8. The organic light-emitting device according to claim 6, wherein, The organic layer containing the compound is a light-emitting layer.

9. The organic light-emitting device according to claim 8, wherein, The light-emitting layer also contains a compound represented by the following chemical formula 2, Chemical formula 2 In the chemical formula 2, A is a benzene ring. B is a naphthalene ring. Ar'1 represents substituted or unsubstituted C. 6-60 aryl; or C containing one or more heteroatoms selected from N, O and S. 2-60 Mixed aromatics, Ar'2 and Ar'3 are each independently substituted or unsubstituted C. 6-60 aryl; or C containing one or more heteroatoms selected from N, O and S. 2-60 Mixed aromatics, R'1 and R'2 are each independently hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or C containing one or more heteroatoms selected from N, O and S. 2-60 Mixed aromatics, a is an integer from 0 to 4. b is an integer from 0 to 6.

10. The organic light-emitting device according to claim 9, wherein, The compounds represented by chemical formula 2 are represented by the following chemical formulas 2-1 to 2-3: Chemical formula 2-1 Chemical formula 2-2 Chemical formula 2-3 In the chemical formulas 2-1 to 2-3, Ar'1, Ar'2, Ar'3, R'1, R'2, a, and b are the same as those defined in claim 9.

11. The organic light-emitting device according to claim 9, wherein, The compound represented by chemical formula 2 is selected from any one of the following compounds:

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