Novel compound and organic light-emitting device comprising same

Abstract

Provided in one embodiment of the present invention is an organic light-emitting device comprising an anode, a cathode and one or more novel compounds.

Description

Novel compound and organic light-emitting device containing the same

[0001] The present invention relates to a novel compound and an organic light-emitting device comprising the same.

[0002] An organic light-emitting diode (OLED) has an organic layer between the anode and the cathode, and on the outside of the anode and / or the cathode.

[0003] An organic light-emitting diode is a self-luminous display device that utilizes the phenomenon in which, when voltage is applied to an anode and a cathode, holes and electrons are generated and supplied to a light-emitting layer between the anode and the cathode, the holes and electrons recombine within the light-emitting layer to generate excitons, and light of a specific wavelength is generated by energy from the generated excitons.

[0004] Organic light-emitting diodes are attracting attention as next-generation display devices because they not only have low power consumption but also have the advantages of a wide viewing angle and fast response speed.

[0005] Meanwhile, as the fields of use and required specifications of organic light-emitting devices diversify, the need for improved luminous efficiency and lifespan is increasing.

[0006] The present invention aims to provide an organic light-emitting device comprising a novel compound and having improved lifespan and efficiency.

[0007] One embodiment of the present invention can provide a compound represented by the following chemical formula 1.

[0008] [Chemical Formula 1]

[0009]

[0010] In the above chemical formula 1,

[0011] wherein Y is O, S, Se or Te;

[0012] The above Ar1 is selected from a substituted or unsubstituted C5-30 aryl group, a substituted or unsubstituted C3-30 heteroaryl group, and a substituted or unsubstituted non-aromatic condensed polycyclic group, except when the above Ar1 is a non-aromatic 4-ring condensed heterocyclic group;

[0013] The above A is selected from a substituted or unsubstituted C5-30 heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group,

[0014] In the above substituted aryl group, substituted heteroaryl group, and substituted non-aromatic condensed polycyclic group, the substituent is selected from deuterium, tritium, halogen, nitro group, nitrile group, sulfide group, naphthyl group, substituted or unsubstituted C1-30 alkyl group, substituted or unsubstituted C2-30 alkenyl group, substituted or unsubstituted C1-30 alkoxy group, substituted or unsubstituted C0-30 silyl group, substituted or unsubstituted C0-30 amine group, and substituted or unsubstituted C3-30 heteroaryl group, except when the substituent is a non-aromatic four-ring condensed heterocyclic group;

[0015] Above X1 to X 16 are each independently C, CH, CD or N;

[0016] The above L may be a direct bond between Ar1 and N, a substituted or unsubstituted C5-30 arylene group, or a substituted or unsubstituted C3-30 heteroarylene group.

[0017] The above Ar1 may be a substituted or unsubstituted C6-20 aryl group, or a substituted or unsubstituted C3-12 heteroaryl group.

[0018] The above A is dibenzofuran, dibenzothiophene, or And,

[0019] Here, * means the position where A is combined, and X9 to X 16 follows the definition in paragraph 1;

[0020] The above Ar2 and Ar3 are each independently selected from hydrogen, halogen, nitro group, nitrile group, sulfide group, substituted or unsubstituted C1-30 alkyl group, substituted or unsubstituted C2-30 alkenyl group, substituted or unsubstituted C1-30 alkoxy group, substituted or unsubstituted C0-30 silyl group, substituted or unsubstituted C0-30 amine group, substituted or unsubstituted C5-30 aryl group, substituted or unsubstituted C5-30 heteroaryl group, and substituted or unsubstituted non-aromatic condensed polycyclic group;

[0021] The above B may be an aryl group of C6-20.

[0022] An organic light-emitting device comprising a novel compound according to the present invention can have improved lifespan and efficiency.

[0023] Figure 1 is a cross-sectional view schematically showing an organic light-emitting device according to one embodiment of the present invention.

[0024] Figure 2 is a cross-sectional view schematically showing an organic light-emitting device according to another embodiment of the present invention.

[0025]

[0026] <Explanation of symbols>

[0027] 10, 10`: Organic light-emitting diode 100: First electrode

[0028] 200: Second electrode 300: Light-emitting layer

[0029] 400: Hole transport layer 410: Hole injection layer

[0030] 420: Hole transport layer 500: Electron transport layer

[0031] 510: Electron injection layer 520: Electron transport layer

[0032] One embodiment of the present invention provides a compound represented by the following chemical formula 1.

[0033] [Chemical Formula 1]

[0034]

[0035] In the above chemical formula 1,

[0036] wherein Y is O, S, Se or Te;

[0037] The above Ar1 is substituted or unsubstituted C 5-30 Aryl group of substituted or unsubstituted C 3-30 A heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group is selected from the group consisting of, but excluding the case where Ar1 is a non-aromatic 4-ring condensed heterocyclic group;

[0038] The above A is substituted or unsubstituted C 5-30 Selected from among heteroaryl groups, substituted or unsubstituted non-aromatic condensed polycyclic groups,

[0039] In the above substituted aryl group, substituted heteroaryl group, and substituted non-aromatic condensed polycyclic group, the substituent is deuterium, tritium, halogen, nitro group, nitrile group, sulfide group, naphthyl group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 3-30 is selected from the heteroaryl group, except when the substituent is a non-aromatic 4-ring condensed heterocyclic group;

[0040] Above X1 to X 16 are each independently C, CH, CD or N;

[0041] The above L is directly bonded to Ar1 and N, or substituted or unsubstituted C 5-30 Arylene group of C, or substituted or unsubstituted C 3-30 It may be a heteroarylene group.

[0042] The above Ar1 is substituted or unsubstituted C 6-20 Aryl group of substituted or unsubstituted C 3-12It may be a heteroaryl group.

[0043] The above A is dibenzofuran, dibenzothiophene, or And,

[0044] Here, * means the position where A is combined, and X9 to X 16 follows the definition in paragraph 1;

[0045] The above Ar2 and Ar3 are each independently hydrogen, halogen, nitro group, nitrile group, sulfide group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 5-30 Aryl group of substituted or unsubstituted C 5-30 is selected from among heteroaryl groups, substituted or unsubstituted non-aromatic condensed polycyclic groups;

[0046] The above B is C 6-20 It can be an aryl group.

[0047]

[0048] One embodiment of the present invention provides a compound represented by the following chemical formula 2.

[0049] [Chemical Formula 2]

[0050]

[0051] In the above chemical formula 2,

[0052] wherein Y is O, S, Se or Te;

[0053] The above Ar1 is substituted or unsubstituted C 5-30 Aryl group of substituted or unsubstituted C 5-30 A heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group is selected from the group consisting of, but excluding the case where Ar1 is a non-aromatic 4-ring condensed heterocyclic group;

[0054] In the above substituted aryl group, substituted heteroaryl group, and substituted non-aromatic condensed polycyclic group, the substituent is hydrogen, deuterium, tritium, halogen, nitro group, nitrile group, sulfide group, naphthyl group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 3-30 is selected from the heteroaryl group, except when the substituent is a non-aromatic 4-ring condensed heterocyclic group;

[0055] The above Ar2 and Ar3 are each independently hydrogen, halogen, nitro group, nitrile group, sulfide group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 5-30 Aryl group of substituted or unsubstituted C 5-30 is selected from among heteroaryl groups, substituted or unsubstituted non-aromatic condensed polycyclic groups;

[0056] The above X1 to X8 are each independently C, CH, CD or N;

[0057] The above L is C, which is directly bonded to Ar1 and N or substituted or unsubstituted. 5-30 Arylene group of C, or substituted or unsubstituted C 5-30 It may be a heteroarylene group.

[0058] The above N and Ar1 can bind at the meta position.

[0059] The above L may be a direct bond.

[0060] The above Ar1 is substituted or unsubstituted C 6-12 It can be an aryl group.

[0061] At least one of the above X1 to X8 may be a CD.

[0062] The above compound can be represented by the following chemical formula 2-1 or 2-2.

[0063] [Chemical Formula 2-1]

[0064] ;

[0065] [Chemical Formula 2-2]

[0066] ;

[0067] In the above chemical formula 2-1 or 2-2, Y and A1 to A3 are as defined in the above chemical formula 2.

[0068] The above Ar1 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0069] The above substituents are deuterium, nitro, nitrile, naphthyl, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 3-12 It can be one of the heteroaryl groups.

[0070] The above substituent may be a deuterium group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted amine group.

[0071]

[0072] In one embodiment of the present invention, the compound may be a compound selected from the group represented by the following chemical formula:

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] In one embodiment of the present invention, the band gap energy of the compound may be 2 to 4 eV, and the T1 level may be 2 eV or higher.

[0080] Another embodiment of the present invention provides an organic light-emitting device comprising an anode, a cathode, and one or more of the compounds.

[0081] One embodiment of the present invention includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer between the anode and the cathode,

[0082] At least one of the hole injection layer, the hole transport layer, and the light-emitting layer may include the compound.

[0083] In one embodiment of the present invention, each of the at least one layer may have a thickness of 10 to 1,000 nm.

[0084] One embodiment of the present invention is illustrated in the accompanying drawings. However, the present invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the scope of the present invention to those skilled in the art. Like reference numerals in the drawings indicate like elements.

[0085] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to limit the invention.

[0086] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. Furthermore, it will be understood that terms defined in commonly used dictionaries should be interpreted to have a meaning consistent with their meaning within the context of the relevant art and the present disclosure, and not in an idealized or overly formal sense.

[0087] While specific embodiments have been described, alternatives, modifications, variations, improvements, and substantial equivalents that are not currently anticipated or unforeseen may occur to the applicant or those skilled in the art. Accordingly, the appended claims, as filed and as amended, are intended to encompass all such alternatives, modifications, variations, improvements, and substantial equivalents.

[0088] In the present invention, the term "alkyl" may be straight-chain or branched, unless otherwise specified, and the number of carbon atoms is not particularly limited, but may be 1 to 40. In one embodiment, the alkyl group has 1 to 30 carbon atoms. In another embodiment, the alkyl group has 1 to 10 carbon atoms. In another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0089] As used herein, the term "alkenyl" refers to an alkyl group that may be straight or branched, unless otherwise specified, and that contains one or more double bonds. The number of carbon atoms is not particularly limited, but may be 2 to 40. In one embodiment, the alkenyl group has 2 to 30 carbon atoms. In another embodiment, the alkenyl group has 2 to 10 carbon atoms. In another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, and the like.

[0090] The term "aryl" as used herein is not particularly limited, but may have 5 to 40 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. In one embodiment, the aryl group has 5 to 30 carbon atoms. In one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like.

[0091] The term "heteroaryl" as used herein refers to a heteroaryl containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but may be 5 to 30 carbon atoms. Examples of heteroaryl include xanthene, thioxanthen, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, Examples thereof include, but are not limited to, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, and may include a condensed polycyclic group.

[0092]

[0093] A compound according to one embodiment of the present invention may be represented by the following chemical formula 1.

[0094] [Chemical Formula 1]

[0095]

[0096] In the above chemical formula 1,

[0097] wherein Y is O, S, Se or Te;

[0098] The above Ar1 is substituted or unsubstituted C 5-30 Aryl group of substituted or unsubstituted C 3-30 A heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group is selected from the group consisting of, but excluding the case where Ar1 is a non-aromatic 4-ring condensed heterocyclic group;

[0099] The above A is substituted or unsubstituted C 5-30Selected from among heteroaryl groups, substituted or unsubstituted non-aromatic condensed polycyclic groups,

[0100] In the above substituted aryl group, substituted heteroaryl group, and substituted non-aromatic condensed polycyclic group, the substituent is deuterium, tritium, halogen, nitro group, nitrile group, sulfide group, naphthyl group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 3-30 is selected from the heteroaryl group, except when the substituent is a non-aromatic 4-ring condensed heterocyclic group;

[0101] Above X1 to X 16 are each independently C, CH, CD or N;

[0102] The above L is directly bonded to Ar1 and N, or substituted or unsubstituted C 5-30 Arylene group of C, or substituted or unsubstituted C 3-30 It is a heteroarylene group.

[0103] The above Ar1 is substituted or unsubstituted C 6-20 Aryl group of substituted or unsubstituted C 3-12 It may be a heteroaryl group.

[0104] The above A is dibenzofuran, dibenzothiophene, or And,

[0105] Here, * means the position where A is combined, and X9 to X 16 follows the definition in paragraph 1;

[0106] The above Ar2 and Ar3 are each independently hydrogen, halogen, nitro group, nitrile group, sulfide group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 5-30 Aryl group of substituted or unsubstituted C 5-30 is selected from among heteroaryl groups, substituted or unsubstituted non-aromatic condensed polycyclic groups;

[0107] The above B is C 6-20 It can be an aryl group.

[0108] When the above A is dibenzofuran or dibenzothiophene, it exhibits high T1 energy characteristics and high hole transport characteristics, and when the above A is carbazole, it can help increase hole transport characteristics while maintaining the high T1 energy characteristics of the core and improve the lifespan of the device due to increased thermal stability.

[0109] The above N and Ar1 can bind to the meta position,

[0110] The above L may be a direct bond.

[0111] The above Ar1 is substituted or unsubstituted C 6-12 It can be an aryl group.

[0112] At least one of the above X1 to X8 may be a CD.

[0113]

[0114] A compound according to one embodiment of the present invention may be represented by the following chemical formula 2:

[0115] [Chemical Formula 2]

[0116]

[0117] In the above chemical formula 2,

[0118] wherein Y is O, S, Se or Te;

[0119] The above Ar1 is substituted or unsubstituted C 5-30Aryl group of substituted or unsubstituted C 5-30 A heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group is selected from the group consisting of, but excluding the case where Ar1 is a non-aromatic 4-ring condensed heterocyclic group;

[0120] In the above substituted aryl group, substituted heteroaryl group, and substituted non-aromatic condensed polycyclic group, the substituent is hydrogen, deuterium, tritium, halogen, nitro group, nitrile group, sulfide group, naphthyl group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 3-30 is selected from the heteroaryl group, except when the substituent is a non-aromatic 4-ring condensed heterocyclic group;

[0121] The above Ar2 and Ar3 are each independently hydrogen, halogen, nitro group, nitrile group, sulfide group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 5-30 Aryl group of substituted or unsubstituted C 5-30 is selected from among heteroaryl groups, substituted or unsubstituted non-aromatic condensed polycyclic groups;

[0122] The above X1 to X8 are each independently C, CH, CD or N;

[0123] The above L is C, which is directly bonded to Ar1 and N or substituted or unsubstituted. 5-30 Arylene group of C, or substituted or unsubstituted C 5-30 It is a heteroarylene group.

[0124] As an optional embodiment, the compound may be represented by the following chemical formula 2-1 or 2-2.

[0125] [Chemical Formula 2-1]

[0126]

[0127] [Chemical Formula 2-2]

[0128]

[0129] In the above chemical formula 2-1 or 2-2,

[0130] The above Y and A1 to A3 are as defined in the above chemical formula 2.

[0131] The above Ar1 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

[0132] The above substituents are deuterium, nitro, nitrile, naphthyl, substituted or unsubstituted C 0-30 Silyl group, substituted or unsubstituted C 0-30 Amine group of C, substituted or unsubstituted 3-12 It can be one of the heteroaryl groups,

[0133] Specifically, the substituent may be a deuterium group, a substituted or unsubstituted silyl group, or a substituted or unsubstituted amine group.

[0134]

[0135] The above compound may be selected from the group represented by the following chemical formula:

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142] The band gap energy of the above compound may be 2 to 4 eV, and the T1 level may be 2 eV or higher, preferably 2 to 10 eV. This facilitates charge balance, which may be effective in improving driving voltage and efficiency.

[0143] An organic light-emitting device according to another embodiment of the present invention may include an anode, a cathode, and one or more of the above compounds.

[0144] Figure 1 illustrates an organic light-emitting device according to one embodiment of the present invention.

[0145] According to FIG. 1, the organic light-emitting device (10) includes a first electrode (100), a second electrode (200), and a light-emitting layer (300).

[0146] The first electrode (100) may serve as an anode to cause the light-emitting layer (300) to emit light. However, this is not limited thereto, and when the second electrode (200) functions as an anode, the first electrode (100) may serve as a cathode.

[0147] As an example, the organic light-emitting element (10) may be a front-emitting type, and as a specific example, light may be mainly emitted in the direction of the second electrode (200). In this case, the first electrode (100) may function as a reflective layer to reduce or prevent light generated from the light-emitting layer (300) from being emitted to the rear. Here, the reflective layer refers to a layer having a property of reflecting light in order to emit light generated from the light-emitting layer to the outside through the second electrode (200). The reflective property may mean that the reflectivity for incident light is about 70% or more and about 100% or less, or about 80% or more and about 100% or less.

[0148] The first electrode (100) according to the present embodiment may include various conductive materials. For example, it may include silver (Ag), aluminum (Al), chromium (Cr), molybdenum (Mo), tungsten (W), titanium (Ti), gold (Au), palladium (Pd) or alloys thereof, and as another example, it may have a triple film structure of silver (Ag) / indium tin oxide (ITO) / silver (Ag) or a triple film structure of indium tin oxide (ITO) / silver (Ag) / indium tin oxide (ITO).

[0149] The second electrode (200) is positioned so as to overlap the first electrode (100), with a light-emitting layer (300) interposed therebetween, as will be described later. The second electrode (200) according to the present embodiment may function as a cathode. However, this is not limited thereto, and when the first electrode (100) functions as a cathode, the second electrode (200) may become an anode.

[0150] The second electrode (200) according to the present embodiment may be a transmissive electrode in which at least a portion of the light generated in the light emitting layer passes through the second electrode and is emitted. Here, the transmissive electrode means that at least a portion of the light incident on the second electrode (200) is transmitted. As an optional embodiment, the second electrode (200) may have a semi-transmissive property in which a portion of the remaining light is reflected back to the first electrode (100). As an optional embodiment, the second electrode (200) may have a reflectivity for incident light of about 0.1% or more and less than about 70%, or about 30% or more and less than 50%.

[0151] The second electrode (200) according to the present embodiment may include various conductive materials, and may include, for example, a transparent conductive material. For example, the second electrode (200) may include a transparent conductive oxide such as ITO or indium zinc oxide (IZO), or silver (Ag), magnesium (Mg), aluminum (Al), chromium (Cr), molybdenum (Mo), tungsten (W), titanium (Ti), gold (Au), palladium (Pd), or an alloy thereof.

[0152] The above light-emitting layer (300) emits light by forming excitons when holes and electrons transferred from the first electrode (100) and the second electrode (200) meet. The light-emitting layer (300) may include the above-described compound, and when the above-described compound has a substituted or unsubstituted phenyl group, a substituted or unsubstituted silane group, or a substituted or unsubstituted amine group introduced with benzofuroindole-carbazole as a nucleus, the driving voltage of the organic light-emitting device may be lowered and the efficiency and lifespan may be further improved.

[0153] The light-emitting layer (300) may include a blue light-emitting layer, a red light-emitting layer, and / or a green light-emitting layer, and may have a single-layer structure in which the blue light-emitting layer, the red light-emitting layer, and / or the green light-emitting layer are each disposed as one layer on the first electrode.

[0154] Blue, red, and green are the three primary colors for expressing color, and various colors can be realized by combining them. The blue light-emitting layer, the red light-emitting layer, and the green light-emitting layer form a blue pixel, a red pixel, and a green pixel, respectively, and the blue light-emitting layer, the red light-emitting layer, and the green light-emitting layer can be arranged in parallel in a direction substantially parallel to the upper surface of the first electrode (100).

[0155] As an optional embodiment, the light-emitting layer may have a structure in which a common color, for example, a blue light-emitting layer, is included, and a color conversion layer corresponding to each light-emitting layer, for example, a color filter, is arranged.

[0156] An organic light-emitting device according to another embodiment of the present invention may further include at least one layer of a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.

[0157] Figure 2 illustrates an organic light-emitting device according to another embodiment of the present invention.

[0158] According to FIG. 2, the organic light-emitting device (10`) may include a first electrode (100), a hole transport layer (400), a light-emitting layer (300), an electron transport layer (500), and a second electrode (200).

[0159] The above hole transport layer (400) may include at least one of a hole injection layer (410) and a hole transport layer (420). The hole injection layer (410) facilitates the injection of holes from the first electrode (100), and the hole transport layer (420) performs the function of smoothly transporting holes transferred from the hole injection layer (410). The hole transport layer (400) may be formed as a double layer in which the hole transport layer (420) is positioned on the hole injection layer (410), or may be formed as a single layer by mixing a material forming the hole injection layer (410) and a material forming the hole transport layer (420).

[0160] An electron transport layer (500) may be further included between the second electrode (200) and the light-emitting layer (300). The electron transport layer (500) may include at least one of an electron injection layer (510) and an electron transport layer (520). The electron injection layer (510) facilitates the injection of electrons from the second electrode (200), and the electron transport layer (520) performs the function of smoothly transporting electrons transferred from the electron injection layer. The electron transport layer (500) may be formed as a double layer in which the electron injection layer (510) is positioned on the electron transport layer (520), or may be formed as a single layer by mixing a material forming the electron injection layer (510) and a material forming the electron transport layer (520).

[0161] However, it is not limited thereto, and the organic light-emitting device according to the modified example may include a light-emitting layer having a multilayer structure.

[0162] At least one of the light-emitting layer (300), hole injection layer (410), hole transport layer (420), electron transport layer (520), and electron injection layer (510) may contain the compound described above. As described below, this can lower the operating voltage of the organic light-emitting device and significantly improve its efficiency and lifespan.

[0163] In addition, each of the at least one layer has a thickness of 10 to 1,000 nm, 10 to 800 nm, 10 to 600 nm, 10 to 400 nm, 10 to 200 nm, 10 to 100 nm, 10 to 50 nm, 50 to 1,000 nm, 50 to 800 nm, 50 to 600 nm, 50 to 400 nm, 50 to 200 nm, 50 to 100 nm, 100 to 1,000 nm, 100 to 800 nm, 100 to 600 nm, 100 to 400 nm, 100 to 200 nm, 200 to 1,000 nm, 200 to 800 nm, 200 to 600 nm, 200 to 400 nm, 400 to 1,000 nm, 400 to 800 nm, 400 to 600 nm, 600 to 1,000 nm, 600 to 800 nm, or 800 to 1,000 nm in thickness.

[0164] The first electrode (100), second electrode (200), and light-emitting layer (300) described above can be applied in the same manner as the above-described embodiment or modified as needed, and a more detailed description thereof is omitted.

[0165]

[0166] Hereinafter, the present invention will be described in detail through synthetic examples, working examples, and experimental examples.

[0167] However, the synthetic examples, working examples, and experimental examples described below are only specific examples of one aspect of the present invention, and the present invention is not limited thereto.

[0168]

[0169] <Synthesis Example 1> Synthesis of IM1 and A

[0170] To synthesize the target compounds, IM1, IM2, and A were synthesized through the following steps.

[0171]

[0172]

[0173] Synthesis of IM1

[0174] In a round-bottomed flask, 20.0 g of Benzofuran-3-boronic acid and 10.0 g of 4-Bromo-2-iodo-1-nitrobenzene were dissolved in 200 mL of 1,4-dioxan, 25 g of K2CO3 (in 40 mL of water) and 42.1 g of Pd(PPh3) were added, and the mixture was stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after the addition of water. The organic layer was extracted with MC, filtered under reduced pressure, and then passed through a silica filter to obtain 14.0 g (yield: 72%) of intermediate IM1.

[0175]

[0176] Synthesis of IM2

[0177] In a round-bottomed flask, 14 g of IM1, 7.4 g of 9H-Carbazole, 14 g of t-BuONa, 31.2 g of Pd2(dba) and 1 g of (t-Bu)3P were dissolved in 140 ml of toluene and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified by column chromatography and recrystallization to obtain 13.7 g of IM2 (yield: 77%).

[0178]

[0179] Synthesis of A

[0180] 14.0 g of the above IM2 was added to a round bottom flask at 60 oAfter dissolving in 150 ml of C MCB, 27 g of triphenylphosphine was added and stirred under reflux for 12 hours. The reaction was confirmed by TLC, and water was added to terminate the reaction. After filtration under reduced pressure, the product was recrystallized to obtain 10.4 g of A (yield: 81%).

[0181]

[0182] Synthesis of C-1, C-2, C-3, C-4, and C-5

[0183] In the IM2 synthesis of A, instead of 9H-Czrbazole, (9-phenyl-9H-carbazol-3-yl)boronic acid, dibenzo[b,d]furan-4-ylboronic acid, dibenzo[b,d]furan-2-ylboronic acid, dibenzo[b,d]thiophen-2-ylboronic acid, or dibenzo[b,d]thiophen-4-ylboronic acid was substituted, and the synthesis was carried out in the same manner as A to synthesize the C-1 to C-5 compounds below.

[0184]

[0185]

[0186] <Synthesis Example 2> Synthesis of IM3 and B

[0187]

[0188]

[0189] Synthesis of IM3

[0190] In a round-bottomed flask, 10 g of IM1, 10.4 g of 9H-3,9'-bicarbazole, 10 g of t-BuONa, 30.86 g of Pd2(dba), and 0.8 g of (t-Bu)3P were dissolved in 100 ml of toluene and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified by column chromatography and recrystallization to obtain 13.2 g of IM3 (yield: 74%).

[0191]

[0192] Synthesis of B

[0193] 13.0 g of the above IM3 was added to a round bottom flask at 60 o After dissolving in 130 ml of C MCB, 20 g of triphenylphosphine was added and stirred under reflux for 12 hours. The reaction was confirmed by TLC, and water was added to terminate the reaction. After filtration under reduced pressure, B 10.3 g (yield: 84%) was obtained by recrystallization.

[0194]

[0195] <Synthesis Example 3> Synthesis of compounds 1 to 40

[0196]

[0197] A 10 g, SM-P1 6.5 g, t-BuONa 7.3 g, Pd2(dba)30.73 g, (t-Bu)3P 0.7 g were dissolved in 100 ml of toluene in a round-bottomed flask and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified by column chromatography and recrystallization to obtain 11 g (yield: 78%) of compound 1.

[0198] Compounds 2 to 40 in Table 1 were synthesized by introducing S or Se instead of O in A in the same manner as in the above compound 1 or by changing the SM-P material.

[0199]

[0200]

[0201] <Synthesis Example 4> Synthesis of compounds 41 to 50

[0202]

[0203] A 10 g, SM-N1 4.9 g, t-BuONa 8 g, Pd2(dba)30.74 g, (t-Bu)3P 0.7 g were dissolved in 100 ml of toluene in a round-bottomed flask and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified by column chromatography and recrystallization to obtain 10.3 g (yield: 81%) of compound 41.

[0204] Compounds 41 to 50 in Table 1 were synthesized by introducing compounds in which S or Se was substituted for O of A in the same manner as compound 41 above or by changing the SM-N material.

[0205]

[0206]

[0207] <Synthesis Example 5> Synthesis of compounds 51 to 76

[0208]

[0209]

[0210] In a round-bottomed flask, 10 g of B, 4.3 g of SM-P1, 6.1 g of t-BuONa, 30.51 g of Pd2(dba) and 0.5 g of (t-Bu)3P were dissolved in 100 ml of toluene and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and then purified by column chromatography and recrystallization to obtain 9.8 g (yield: 77%) of compound 51.

[0211] Compounds 51 to 71 in Table 1 were synthesized by introducing compounds in which S or Se was substituted for O of B in the same manner as compound 51 above, or by changing the SM-P and SM-N materials. In addition, compounds 72 to 76 were synthesized by using compound C instead of B and synthesizing SM-P1 in the same manner as above.

[0212]

[0213]

[0214]

[0215] <Example> Manufacturing of organic light-emitting devices

[0216] The organic light-emitting device was stacked in the following order from the bottom: anode (hole injection electrode (ITO)) / hole injection and transport layer (HTL) / hole transport and emission layer (P-Host) / emission layer (P-Host:N-Host:Dopant) / electron transport layer (ETL) / electron injection layer / cathode.

[0217] The substrate may be a transparent glass substrate or a flexible plastic substrate when manufacturing an organic light-emitting device.

[0218] The hole injection electrode serves as the anode for hole injection in organic light-emitting devices. It utilizes a material with a low work function to facilitate hole injection, and can be formed from transparent materials such as ITO, IZO, or graphene.

[0219] A cathode for electron injection is formed on the electron injection layer. Various metals can be used as the cathode. Specific examples include aluminum, gold, and silver.

[0220]

[0221] Example 1

[0222] A glass substrate coated with a 1500 Å thick indium tin oxide (ITO) thin film was ultrasonically washed in distilled water. After washing with distilled water, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol and dried. After transferring it to a plasma cleaner, the substrate was cleaned for 5 minutes using oxygen plasma. Then, a hole injection and transport layer HI01 of 1300 Å and a P-Host of 50 Å were formed on the ITO substrate using a thermal evaporator, and then the light-emitting layer was doped with P-Host:N-Host:Dopant to form a 350 Å thickness. Next, an electron transport layer of 300 Å, a block layer of 50 Å, and an active layer of Ag:Mg of 120 Å thickness were formed, and this device was encapsulated in a glove box to form an organic light-emitting device.

[0223]

[0224] Examples 2 to 40

[0225] Examples 2 to 40 used compounds 2 to 33 as P-Host and Bphene as N-Host. Then, an organic light-emitting device was manufactured in the same manner as Example 1.

[0226]

[0227] Comparative Examples 1 to 12

[0228] Comparative Examples 1 to 11 used comparative compounds 1 to 11 and CBP as P-Hosts and Bphene as N-Hosts, and Comparative Example 12 used CBP as P-Hosts and Bphene as N-Hosts. An organic light-emitting device was manufactured using the same method as Example 1.

[0229]

[0230] Examples 41 to 50

[0231] Examples 41 to 50 used CBP as a P-Host and compounds 41 to 50 and Bphene as N-Hosts. An organic light-emitting device was manufactured using the same method as Example 1.

[0232]

[0233] Examples 51 to 56

[0234] Examples 51 to 56 simultaneously used compounds 1 and 9 as P-Hosts and compounds 42, 44, and 46 as N-Hosts of the present invention, and produced organic light-emitting devices in the same manner as Example 1.

[0235]

[0236] <Experimental Example> Performance Evaluation of Organic Light-Emitting Diodes

[0237] The performance of the organic light-emitting devices of the examples and comparative examples was evaluated by measuring the current density and luminance in response to the applied voltage under atmospheric pressure conditions by applying voltage using a Keithley 2400 source measurement unit to inject electrons and holes and measuring the luminance when light is emitted using a Konica Minolta spectroradiometer (CS-2000). The results are shown in Tables 2 to 4 below.

[0238] ITO / HTL(HT0.1_130nm) / p-Host(5nm) / p-Host:n-Host:Dopant(35nm) / ETL(31nm) / Ag:Mg(12nm,10:1) / (@1000 cd / m 2 )

[0239]

[0240] Op. VCd / Alm / wE.QE(%)CIExCIEyLT95Example 14.1018.4114.1237.140.1340.05665Example 24.1017.8113.6637.390.1360.05562Example 34.1317.8713.6737.410.1360.05566Example 44.2317.412.7635.140.1340.05651Example 54.2417.5212.8435.440.1360.05551Example 64.2917.6512.9435.640.1340.05655Example 74.2117.3212.9235.090.1360.05551 Example 84.118.6214.2837.820.1340.05657 Example 94.1118.6814.2937.830.1360.05560 Example 104.3217.7813.1636.010.1340.05655 Example 114.0918.3114.0937.930.1360.05556 Example 124.3017.7012.9735.720.1340.05651 Example 134.3918.0613.1736.590.1360.05556Example 144.3417.8613.0936.050.1340.05654Example 154.4418.2713.6337.010.1360.05554Example 164.6117.0811.6434.970.1340.05655Example 174.4116.8611.9834.250.1360.05545Example 184.5017.2012.2234.950.1340.05644Example 194.4716.5611.2933.910.1360.05547 Example 204.4116.3411.1433.450.1340.05648 Example 214.3817.0112.0434.040.1360.05546 Example 224.4216.9012.0134.330.1350.05744 Example 234.3516.6311.8133.780.1350.05743 Example 244.4717.0912.1434.710.1350.05746 Example 254.4416.4511.2133.680.1350.05745 Example 264.5216.7511.4134.290.1350.05746 Example 274.4217.1212.3435.440.1350.05747 Example 284.1017.8113.6637.390.1360.05573 Example 294.1018.4114.1237.140.1340.05674 Example 304.1118.6814.2937.830.1360.05582 Example 314.3115.9211.5332.410.1350.05841 Example 324.3915.4912.2332.080.1350.05840 Example 334.3515.7212.4132.120.1350.05840 Example 344.3116.0212.4833.010.1350.05942 Example 354.3316.0512.1633.020.1350.05944 Example 364.3515.8412.2132.460.1350.05941 Example 374.3715.8712.2432.480.1350.05942 Example 384.6514.5711.5431.650.1350.05935 Example 394.6814.2111.4831.430.1350.05936 Example 404.7214.111.3431.040.1350.05935 Comparative Example 15.4911.776.7524.480.1350.05814 Comparative Example 25.4015.810.032.30.1340.05824 Comparative Example 35.0015.779.5232.210.1330.05922 Comparative Example 44.5815.3710.5631.890.1330.05724 Comparative Example 54.8315.9510.3830.800.1320.06330Comparative example 64.9914.999.4330.480.1330.05927Comparative example 74.6315.8710.7730.990.1320.06233Comparative example 85.6710.115.6120.560.1340.05723Comparative example 95.2111.907.1825.070.1350.05522Comparative example 105.6411.616.4723.750.1340.05824Comparative example 114.9712.077.5622.510.1340.05933Comparative Example 12 (CBP-Bphene)5.669.535.3019.550.1340.05831.

[0241]

[0242] Op. VCd / Alm / wE.QE(%)CIExCIEyLT95Example 414.1616.8212.7336.070.1370.05351Example 424.1118.0513.8337.340.1350.05757Example 434.1616.5712.5235.840.1370.05651Example 444.1518.0013.8037.150.1350.05759Example 454.4516.8711.9134.740.1340.05750Example 464.1617.7813.7437.080.1350.05752Example 474.8516.1610.4633.490.1340.05739Example 484.6016.0510.9533.520.1340.05738Example 494.4016.4411.2333.930.1340.05737Example 504.5116.8311.3434.010.1340.05736Comparative Example 12 (CBP-Bphene) 5.669.535.3019.550.1340.05831

[0243]

[0244] Op. VCd / Alm / wE.QE(%)CIExCIEyLT95Example 51(Compound 1+42)4.0918.6814.3637.730.1340.05766Example 52(Compound 1+44)4.0919.3514.8838.270.1340.05769Example 53(Compound 1+46)4.0819.0114.6637.990.1340.05767Example 54(Compound 9+42)4.0719.4315.0037.910.1340.05771Example 55 (Compound 9+44) 4.11 19.05 14.58 38.60 0.134 0.05770 Example 56 (Compound 9+46) 4.08 18.86 14.54 38.39 0.134 0.05765

[0245] As shown in Tables 2 to 4 above, the examples of the present invention have improved efficiency and lifespan compared to Comparative Examples 1 to 12, and it can be confirmed that they have excellent physical properties in all aspects.

[0246] Specifically, comparing the examples of the present invention, when the phenyl part of benzofuroindole is bonded to the N side of carbazole, when bonded to the phenyl side of carbazole, or when benzofuroindole is bonded to DBF or DBT, the examples showed higher performance compared to the device results using CBP, a general P-Host material, and Bphene, an N-Host material. In particular, in the examples, when carbazole is bonded to the N side of benzofuroindole and when D is substituted instead of H, it can be confirmed that the lifespan is improved.

[0247] Compared to Comparative Examples 5 to 7, in the case of the example, the driving voltage was lowered as the Hole characteristic increased through direct bonding of carbazole, and thus the efficiency and lifespan were shown to increase.

[0248] In addition, in Examples 16 to 27, where compounds in which S and Se were substituted instead of O were applied as P-Hosts, and in Examples 41 to 50, where compounds in which S and Se were substituted instead of O were applied as N-Hosts, higher performance was exhibited compared to the comparative examples. In particular, it can be seen that when the compound of the present invention in which a substituted or unsubstituted phenyl group is introduced into benzofuroindole-carbazole is included, the driving voltage is lowered, and the efficiency and lifespan are greatly improved.

[0249] Compounds 1 and 9 showed high performance as P-Hosts, and compounds 42, 44, and 46 showed high performance as N-Hosts. In particular, the best efficiency and lifespan were observed when the Host of the present invention was simultaneously applied as both P-Host and N-Host. This suggests that the device characteristics are optimized due to the high T1 energy characteristics of the core.

[0250]

[0251] The foregoing description of the present invention is for illustrative purposes only, and those skilled in the art will readily appreciate that the present invention can be readily modified into other specific forms without altering the technical spirit or essential characteristics of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive. For example, each component described as a single entity may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined manner.

[0252] The scope of the present invention is indicated by the claims described below, and all changes or modifications derived from the meaning and scope of the claims and their equivalent concepts should be interpreted as being included in the scope of the present invention.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, wherein Y is O, S, Se or Te; The above Ar1 is substituted or unsubstituted C 5-30 Aryl group of C, substituted or unsubstituted 3-30 A heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group is selected from among Ar1, except in the case where Ar1 is a non-aromatic 4-ring condensed heterocyclic group; The above A is substituted or unsubstituted C 5-30 is selected from among heteroaryl groups, substituted or unsubstituted non-aromatic condensed polycyclic groups, In the above substituted aryl group, substituted heteroaryl group, and substituted non-aromatic condensed polycyclic group, the substituent is deuterium, tritium, halogen, nitro group, nitrile group, sulfide group, naphthyl group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 C, substituted or unsubstituted, of 0-30 Amine group of C, substituted or unsubstituted 3-30 is selected from the heteroaryl group of , except when the substituent is a non-aromatic 4-ring condensed heterocyclic group; Above X1 to X 16 are each independently C, CH, CD or N; The above L is directly bonded to Ar1 and N, or substituted or unsubstituted C. 5-30 Arylene group of C, or substituted or unsubstituted C 3-30 It is a heteroarylene group.

2. In paragraph 1, The above Ar1 is substituted or unsubstituted C 6-20 Aryl group of C, substituted or unsubstituted 3-12A compound having a heteroaryl group.

3. In paragraph 1, The above A is dibenzofuran, dibenzothiophene, or And, Here, * indicates the position where A is combined, and X9 to X 16 follows the definition in Article 1; The above Ar2 and Ar3 are each independently hydrogen, halogen, nitro group, nitrile group, sulfide group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 C, substituted or unsubstituted, of 0-30 Amine group of C, substituted or unsubstituted 5-30 Aryl group of C, substituted or unsubstituted 5-30 A heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group is selected from; The above B is C 6-20 A compound having an aryl group.

4. In paragraph 1, A compound represented by the following chemical formula 2: [Chemical formula 2] In the above chemical formula 2, wherein Y is O, S, Se or Te; The above Ar1 is substituted or unsubstituted C 5-30 Aryl group of C, substituted or unsubstituted 5-30 A heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group is selected from among Ar1, except in the case where Ar1 is a non-aromatic 4-ring condensed heterocyclic group; In the above substituted aryl group, substituted heteroaryl group, and substituted non-aromatic condensed polycyclic group, the substituent is hydrogen, deuterium, tritium, halogen, nitro group, nitrile group, sulfide group, naphthyl group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 C, substituted or unsubstituted, of 0-30 Amine group of C, substituted or unsubstituted 3-30 is selected from the heteroaryl group of , except when the substituent is a non-aromatic 4-ring condensed heterocyclic group; The above Ar2 and Ar3 are each independently hydrogen, halogen, nitro group, nitrile group, sulfide group, substituted or unsubstituted C 1-30 Alkyl group of C, substituted or unsubstituted 2-30 Alkenyl group of C, substituted or unsubstituted 1-30 Alkoxy group, substituted or unsubstituted C 0-30 C, substituted or unsubstituted, of 0-30 Amine group of C, substituted or unsubstituted 5-30 Aryl group of C, substituted or unsubstituted 5-30 A heteroaryl group, a substituted or unsubstituted non-aromatic condensed polycyclic group is selected from; The above X1 to X8 are each independently C, CH, CD or N; The above L is C, which is directly bonded to Ar1 and N or substituted or unsubstituted. 5-30 Arylene group of C, or substituted or unsubstituted C 5-30 It is a heteroarylene group.

5. In paragraph 1, A compound in which the above N and Ar1 are bonded at the meta position.

6. In paragraph 1, A compound in which the above L is a direct bond.

7. In paragraph 1, The above Ar1 is substituted or unsubstituted C6-12 A compound having an aryl group.

8. In paragraph 1, A compound wherein at least one of the above X1 to X8 is CD.

9. In paragraph 4, The above compound is a compound represented by the following chemical formula 2-1 or 2-2: [Chemical Formula 2-1] ; [Chemical Formula 2-2] In the above chemical formula 2-1 or 2-2, The above Y and A1 to A3 are as defined in Article 4.

10. In paragraph 1, A compound wherein the above Ar1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted naphthyl.

11. In paragraph 1, The above substituents are deuterium, nitro, nitrile, naphthyl, substituted or unsubstituted C 0-30 C, substituted or unsubstituted, of 0-30 Amine group of C, substituted or unsubstituted 3-12 A compound, which is one of the heteroaryl groups.

12. In paragraph 1, A compound wherein the substituent is deuterium, a substituted or unsubstituted silyl group, or a substituted or unsubstituted amine group.

13. In paragraph 1, The above compound is a compound selected from the group represented by the following chemical formula:

14. In paragraph 1, A compound having a band gap energy of 2 to 4 eV and a T1 level of 2 eV or higher.

15. An organic light-emitting device comprising an anode, a cathode, and at least one first compound.

16. In paragraph 15, It comprises a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer between the anode and the cathode, An organic light-emitting device, wherein at least one of the hole injection layer, the hole transport layer, and the light-emitting layer comprises the first compound.

17. In paragraph 16, An organic light-emitting device, wherein each of said at least one layer has a thickness of 10 to 1,000 nm.

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