Heterocyclic compound, organic light-emitting device comprising same, and composition for organic material layer of organic light-emitting device

Abstract

Disclosed are a heterocyclic compound of chemical formula 1, an organic light-emitting device comprising the same, and a composition for an organic material layer of the organic light-emitting device.

Description

[0001] Cross - reference to related applications

[0002] This application claims the priority and benefit of Korean Patent Application No. 10 - 2023 - 0171543, filed with the Korean Intellectual Property Office on November 30, 2023, the entire contents of which are incorporated herein by reference. Technical field

[0003] This specification relates to heterocyclic compounds, organic light - emitting devices including the same, and compositions for organic material layers of organic light - emitting devices. Background art

[0004] An electroluminescent device is a self - emitting display device and has advantages such as a wide viewing angle, excellent contrast, and a fast response speed.

[0005] An organic light - emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light - emitting device having the structure, electrons and holes injected from the two electrodes combine with each other in pairs in the organic thin film and then emit light while annihilating. If necessary, the organic thin film may be composed of a single layer or multiple layers.

[0006] If necessary, the material for the organic thin film may have a light - emitting function. For example, as the material for the organic thin film, a compound that can individually form a light - emitting layer by itself may also be used, or a compound that can act as a host or a dopant for a host - dopant - based light - emitting layer may also be used. In addition, as the material for the organic thin film, a compound that can play the following roles may also be used: for example, hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection.

[0007] In order to improve the performance, service life, or efficiency of organic light - emitting devices, there is a continuous need to develop materials for organic thin films.

[0008] [Related technical documents]

[0009] [Patent documents]

[0010] (Patent Document 1) U.S. Patent No. 4,356,429 Summary of the invention

[0011] The present invention is directed to providing heterocyclic compounds, organic light - emitting devices including the same, and compositions for organic material layers of organic light - emitting devices.

[0012] An exemplary embodiment of the present invention provides a heterocyclic compound of the following Chemical Formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] X is O or S,

[0017] L is a direct bond; a substituted or unsubstituted C6 - C60 arylene; or a substituted or unsubstituted C2 - C60 heteroarylene,

[0018] Ar is a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C3 - C60 cycloalkyl; a substituted or unsubstituted C2 - C60 heterocycloalkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0019] R is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C1 - C60 haloalkyl; a substituted or unsubstituted C3 - C60 cycloalkyl; a substituted or unsubstituted C2 - C60 heterocycloalkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, and

[0020] m is an integer from 1 to 9, and when m is 2 or greater, the substituents in parentheses are the same as or different from each other.

[0021] Another exemplary embodiment provides an organic light - emitting device, which includes: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers in the organic material layer contain one or more of the heterocyclic compounds.

[0022] Yet another exemplary embodiment provides a composition for an organic material layer of an organic light - emitting device, which contains the heterocyclic compound.

[0023] When used in an organic light - emitting device, the heterocyclic compounds described in this specification can reduce the driving voltage of the device, improve the luminous efficiency, and improve the service - life characteristics of the device. Specifically, when in the heterocyclic compounds of the present invention, as shown in Chemical Formula 1, the 6 - positions of two identical naphthobenzofuranyl / naphthobenzothienyl groups are bonded to triazine, and this heterocyclic compound is used as a light - emitting layer material, the performance of the device can be effectively improved. As described above, triazine is bonded to a specific position of two identical naphthobenzofuranyl / naphthobenzothienyl groups to have a symmetric structure, thereby expanding the conjugation of the molecule and having a suitable bandgap and homo energy level. Therefore, charge transfer is promoted, resulting in the effect of improving the luminous efficiency. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figures 1 to 3A diagram exemplarily showing the stacked structure of an organic light-emitting device according to an exemplary embodiment of the present specification. Detailed Description

[0025] Hereinafter, the present specification will be described in more detail.

[0026] In the present specification, when a part "includes" a constituent element, unless otherwise specifically described, this does not mean excluding other constituent elements, but means that other constituent elements can also be included.

[0027] In the present specification, "N to N'" means N or more and N' or less.

[0028] In the present specification, for the chemical formula means the position where the constituent elements are bonded.

[0029] The term "substituted" means that a hydrogen atom bonded to a carbon atom or a nitrogen atom of a compound becomes another substituent, and there is no limitation on the position to be substituted as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substitutions are made, the two or more substituents can be the same or different from each other.

[0030] In the present specification, "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium; halogen group; -CN; C1 to C60 alkyl; C2 to C60 alkenyl; C2 to C60 alkynyl; C1 to C60 haloalkyl; C1 to C60 alkoxy; C6 to C60 aryloxy; C1 to C60 alkylthio; C6 to C60 arylthio; C1 to C60 alkylsulfonyl; C6 to C60 arylsulfonyl; C3 to C60 cycloalkyl; C2 to C60 heterocycloalkyl; C6 to C60 aryl; C2 to C60 heteroaryl; silyl; phosphinyl; and amino, or a substituent in which two or more substituents selected from the exemplified substituents are connected to each other.

[0031] In the present specification, Cn1 to Cn2 (n1 and n2 are integers of 1 or greater) means the range of carbon atoms. For example, C1 to C60 alkyl means an alkyl having 1 to 60 carbon atoms.

[0032] In the present specification, "when a substituent is not shown in the chemical formula or the structure of a compound" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( 2 H) is an isotope of hydrogen, some hydrogen atoms can be deuterium.

[0033] In an exemplary embodiment of the present application, "when a substituent is not shown in the chemical formula or the structure of a compound" may mean that all positions where the substituent can reach are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be deuterium which is an isotope. In this case, the deuterium content may be from 0% to 100%, and the deuterium content may be expressed as the deuterium substitution rate.

[0034] In an exemplary embodiment of the present application, in the case of "when a substituent is not shown in the chemical formula or the structure of a compound", when the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents do not explicitly exclude deuterium such as hydrogen, hydrogen and deuterium can be mixed and used in the compound.

[0035] In an exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen, an element having a deuteron composed of one proton and one neutron as its nucleus, and can be represented by hydrogen-2, and the element symbol can also be represented as D or 2 H.

[0036] In an exemplary embodiment of the present application, an isotope means an atom having the same atomic number (Z) but a different mass number (A), and can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0037] In an exemplary embodiment of the present application, when the total number of substituents of a base compound is defined as T1 and the number of a specific substituent among the substituents is defined as T2, the substitution rate T% of the specific substituent can be defined as T2 / T1×100 = T%.

[0038] That is, in one example, when the total number of substituents that a phenyl group can have is 5 (T1 in the formula) and the number of deuterium among the substituents is 1 (T2 in the formula), the 20% deuterium substitution rate of the phenyl group represented can be expressed as 20%. That is, the 20% deuterium substitution rate of the phenyl group can be represented by the following structural formula.

[0039]

[0040] In addition, in an exemplary embodiment of the present application, "a phenyl group with a deuterium substitution rate of 0%" may mean that no deuterium atom is included as a substituent, that is, a phenyl group having five hydrogen atoms.

[0041] In this specification, a halogen may be fluorine, chlorine, bromine or iodine.

[0042] In the present specification, alkyl includes straight-chain or branched-chain having 1 to 60 carbon atoms, and may be additionally substituted with additional substituents. The number of carbon atoms of the alkyl may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof 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, nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

[0043] In the present specification, alkenyl includes straight-chain or branched-chain having 2 to 60 carbon atoms, and may be additionally substituted with additional substituents. The number of carbon atoms of the alkenyl may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethenyl-1-yl, 2-phenylethenyl-1-yl, 2,2-diphenylethenyl-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl-1-yl)ethenyl-1-yl, yl, styryl, etc., but are not limited thereto.

[0044] In the present specification, alkynyl includes straight-chain or branched-chain having 2 to 60 carbon atoms, and may be additionally substituted with additional substituents. The number of carbon atoms of the alkynyl may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0045] In the present specification, haloalkyl means alkyl substituted with a halogen group, and specific examples thereof include -CF 3 、-CF 2 CF 3 etc., but are not limited thereto.

[0046] In the present specification, alkoxy is represented by -O(R101), and the above examples of alkyl can be applied to R101.

[0047] In the present specification, aryloxy is represented by -O(R102), and the above examples of aryl can be applied to R102.

[0048] In this specification, an alkylthio group is represented by -S(R103), and the above examples of alkyl groups can be applied to R103.

[0049] In this specification, an arylthio group is represented by -S(R104), and the above examples of aryl groups can be applied to R104.

[0050] In this specification, an alkylsulfonyl group is represented by -S(=O) 2 (R105), and the above examples of alkyl groups can be applied to R105.

[0051] In this specification, an arylsulfonyl group is represented by -S(=O) 2 (R106), and the above examples of aryl groups can be applied to R106.

[0052] In this specification, cycloalkyl includes monocyclic or polycyclic groups having 3 to 60 carbon atoms, and may be additionally substituted with additional substituents. Here, polycyclic means a group in which a cycloalkyl group is directly connected or fused to another cyclic group. Here, the other cyclic group may also be a cycloalkyl group, but may also be another cyclic group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms in the cycloalkyl group can be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0053] In this specification, heterocycloalkyl contains O, S, Se, N or Si as a heteroatom, includes monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be additionally substituted with additional substituents. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected or fused to another cyclic group. Here, the other cyclic group may also be a heterocycloalkyl group, but may also be another cyclic group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms in the heterocycloalkyl group can be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0054] In this specification, aryl includes monocyclic or polycyclic groups having 6 to 60 carbon atoms, and may be additionally substituted with additional substituents. Here, polycyclic means a group in which an aryl group is directly connected or fused to another cyclic group. Here, the other cyclic group may also be an aryl group, but may also be another cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. Aryl includes spiro groups. The number of carbon atoms in the aryl group can be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of aryl include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, a base, a phenanthrene base, a base, a fluoranthene base, a triphenylene, a phenalenyl, a pyrene base, a tetracenyl, a pentacenyl, a fluorene base, an indenyl, an acenaphthylenyl, a benzo[b]fluorene base, a spirobifluorene base, a 2,3-dihydro-1H-indenyl, a fused cyclic group thereof, etc., but not limited thereto.

[0055] In this specification, the terphenyl may be selected from the following structures.

[0056]

[0057] In this specification, the fluorene base may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0058] When the fluorene base is substituted, the substituent may have the following structures, but not limited thereto.

[0059]

[0060] In this specification, the heteroaryl contains S, O, Se, N or Si as a heteroatom, includes a monocyclic or polycyclic having 2 to 60 carbon atoms, and may be additionally substituted with additional substituents. Herein, the polycyclic means a group in which the heteroaryl is directly connected or fused to another cyclic group. Herein, the other cyclic group may also be a heteroaryl, but may also be another cyclic group, such as a cycloalkyl, a heterocycloalkyl, an aryl, etc. The number of carbon atoms of the heteroaryl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl include a pyridyl, a pyrrolyl, a pyrimidinyl, a pyridazinyl, a furyl, a thienyl, an imidazolyl, a pyrazolyl, an oxazolyl, an iso oxazolyl, a thiazolyl, an isothiazolyl, a triazolyl, a furazanyl, a dioxazolyl, a thiadiazolyl, a dithiazolyl, a tetrazolyl, a pyranyl, a thiopyranyl, a diazinyl, a thiazinyl, a di benzofuranyl, a triazinyl, a tetrazinyl, a quinolinyl, an isoquinolinyl, a quinazoline group, an isoquinazolinyl, a quinozoline group, a naphthyridinyl, an acridinyl, a phenanthridinyl, an imidazopyridyl, a phthalazinyl, a triazaindenyl, an indolyl, an indazolyl, a benzothiazolyl, a benzo oxazolyl, a benzimidazolyl, a benzothienyl, a benzofuranyl, a dibenzothienyl, a dibenzofuranyl, a carbazolyl, a benzocarbazolyl, a dibenzocarbazolyl, a phenazinyl, a dibenzosilolyl, a spirobis(dibenzosilol), a dihydrophenazinyl, a phen A quinolizinyl group, a phenanthridinyl group, a thienyl group, an indolo[2,3-a]carbazolyl group, an indolo[2,3-b]carbazolyl group, a dihydroindolyl group, a 10,11-dihydro-dibenzo[b,f]azepinyl group, a 9,10-dihydroacridinyl group, a phenanthrazine group, a phenothiazinyl group, a phthalazinyl group, a phenanthrolinyl group, a naphthobenzo[1,2-b]furan group, a naphthobenzo[1,2-b]thiophene group, a benzo[c][1,2,5]thiadiazolyl group, a 2,3-dihydrobenzo[b]thienyl group, a 2,3-dihydrobenzofuranyl group, a 5,10-dihydrodibenzo[b,e][1,4]azasilanyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]dihydroindolyl group, a 5,11-dihydroindeno[1,2-b]carbazolyl group, etc., but not limited thereto.

[0061] In this specification, the benzocarbazolyl group may be any one of the following structures.

[0062]

[0063] In this specification, the dibenzocarbazolyl group may be any one of the following structures.

[0064]

[0065] In this specification, when the substituent is a carbazolyl group, a benzocarbazolyl group, or a dibenzocarbazolyl group, it means bonding to the nitrogen or carbon of the carbazolyl group, benzocarbazolyl group, or dibenzocarbazolyl group.

[0066] In this specification, when the carbazolyl group, benzocarbazolyl group, or dibenzocarbazolyl group is substituted, the additional substituent may be substituted at the nitrogen or carbon of the carbazolyl group, benzocarbazolyl group, or dibenzocarbazolyl group.

[0067] In this specification, the naphthobenzo[1,2-b]furan group may be any one of the following structures.

[0068]

[0069] In this specification, the naphthobenzo[1,2-b]thiophene group may be any one of the following structures.

[0070]

[0071] In this specification, the silyl group contains Si and is a substituent directly connected to the Si atom as a group, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same or different from each other, and may each independently be a substituent composed of at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0072] Depending on the substituents bonded to the Si element, silyl groups can include alkylsilyl, arylsilyl, heteroarylsilyl, alkylarylsilyl, arylheteroarylsilyl, etc. Alkylsilyl, arylsilyl, or heteroarylsilyl means that the alkyl, aryl, or heteroaryl is respectively substituted by the Si element of the silyl group, alkylarylsilyl means that the alkyl and aryl are substituted by the Si element of the silyl group, and arylheteroarylsilyl means that the aryl and heteroaryl are substituted by the Si element of the silyl group.

[0073] Specific examples of silyl groups include the following structures, but are not limited thereto.

[0074]

[0075]

[0076] In the present specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same or different from each other, and can each independently be a substituent composed of at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specifically, the phosphine oxide group can be substituted by an alkyl or aryl group, and the above examples can be applied to alkyl and aryl groups. Examples of the phosphine oxide group include dimethylphosphine oxide group, diphenylphosphine oxide group, dinaphthylphosphine, etc., but are not limited thereto.

[0077] In the present specification, the amino group is represented by -N(R112)(R113), and R112 and R113 are the same or different from each other, and can each independently be a substituent composed of at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amino group can be selected from: -NH 2 ; monoalkylamino; monoarylamino; monoheteroarylamino; dialkylamino; diarylamino; diheteroarylamino; alkylarylamino; alkylheteroarylamino; and arylheteroarylamino, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, dibiphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, phenylnaphthylamino, xylanylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenyltriphenylenylamino, biphenyltriphenylenylamino, etc., but are not limited thereto.

[0078] In the present specification, the above description of the aryl group can be applied to the arylene group, except that the arylene group is divalent.

[0079] In this specification, the above description of heteroaryl can be applied to heteroarylene, with the difference that heteroarylene is divalent.

[0080] An exemplary embodiment of this specification provides a heterocyclic compound of the following Chemical Formula 1.

[0081] [Chemical Formula 1]

[0082]

[0083] In Chemical Formula 1,

[0084] X is O or S,

[0085] L is a direct bond; a substituted or unsubstituted C6 - C60 arylene; or a substituted or unsubstituted C2 - C60 heteroarylene,

[0086] Ar is a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C3 - C60 cycloalkyl; a substituted or unsubstituted C2 - C60 heterocycloalkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl,

[0087] R is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 - C60 alkyl; a substituted or unsubstituted C1 - C60 haloalkyl; a substituted or unsubstituted C3 - C60 cycloalkyl; a substituted or unsubstituted C2 - C60 heterocycloalkyl; a substituted or unsubstituted C6 - C60 aryl; or a substituted or unsubstituted C2 - C60 heteroaryl, and

[0088] m is an integer from 1 to 9, and when m is 2 or greater, the substituents in the parentheses are the same or different from each other.

[0089] The heterocyclic compound according to an exemplary embodiment of this specification has two identical naphthobenzofuranyl / naphthobenzothiophenyl as substituents of the triazine group, and the structure and substitution position of the naphthobenzofuranyl / naphthobenzothiophenyl are specific. By having such a structure, the compound is helpful for improving the performance of an organic light - emitting device when used as a material for an organic light - emitting device.

[0090] That is, in Chemical Formula 1 above, the two have the same structure. Specifically, the two have the same type of substituent R at the same position. In this structure, is the position bonded to the triazine.

[0091] In one exemplary embodiment of the present specification, X may be O.

[0092] In one exemplary embodiment of the present specification, X may be S.

[0093] In one exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-O or 1-S.

[0094] [Chemical Formula 1-O]

[0095]

[0096] [Chemical Formula 1-S]

[0097]

[0098] In Chemical Formulas 1-O and 1-S,

[0099] the definition of each substituent is the same as that in Chemical Formula 1.

[0100] In one exemplary embodiment of the present specification, L may be a direct bond; a substituted or unsubstituted C6-C30 arylene; or a substituted or unsubstituted C2-C30 heteroarylene.

[0101] In one exemplary embodiment of the present specification, L may be a direct bond; a substituted or unsubstituted C6-C20 arylene; or a substituted or unsubstituted C2-C20 heteroarylene.

[0102] In one exemplary embodiment of the present specification, L may be a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted naphthylene; a substituted or unsubstituted divalent dibenzofuranyl; a substituted or unsubstituted divalent dibenzothiophenyl; or a substituted or unsubstituted divalent carbazolyl.

[0103] In one exemplary embodiment of the present specification, L may be a direct bond; an unsubstituted or deuterium-substituted C6-C60 arylene; or an unsubstituted or deuterium-substituted C2-C60 heteroarylene.

[0104] In one exemplary embodiment of the present specification, L may be a direct bond; an unsubstituted or deuterium-substituted C6-C30 arylene; or an unsubstituted or deuterium-substituted C2-C30 heteroarylene.

[0105] In one exemplary embodiment of the present specification, L may be a direct bond; an unsubstituted or deuterium-substituted C6-C20 arylene; or an unsubstituted or deuterium-substituted C2-C20 heteroarylene.

[0106] In an exemplary embodiment of the present specification, L may be a direct bond; an unsubstituted or deuterium-substituted phenylene; an unsubstituted or deuterium-substituted naphthylene; an unsubstituted or deuterium-substituted divalent dibenzofuranyl; an unsubstituted or deuterium-substituted divalent dibenzothiophenyl; or an unsubstituted or deuterium-substituted divalent carbazolyl.

[0107] In an exemplary embodiment of the present specification, L may be a direct bond or selected from the following structures.

[0108]

[0109] In the said structure, is the position bonded to the triazine group and Ar, and the said structure may be further deuterium-substituted.

[0110] In an exemplary embodiment of the present specification, Ar may be a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C2-C30 heterocycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0111] In an exemplary embodiment of the present specification, Ar may be a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0112] In an exemplary embodiment of the present specification, Ar may be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0113] In an exemplary embodiment of the present specification, Ar may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluoranthenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group; a substituted or unsubstituted carbazolyl group; a substituted or unsubstituted naphthobenzofuranyl group; or a substituted or unsubstituted naphthobenzothiophenyl group.

[0114] In an exemplary embodiment of the present specification, Ar may be a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a phenanthryl group; a triphenylene group; a fluoranthenyl group; a fluorenyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a carbazolyl group; a naphthobenzofuranyl group; or a naphthobenzothiophenyl group, and Ar may be further substituted with one or more substituents selected from deuterium, halogen groups, alkyl groups, aryl groups, and heteroaryl groups or two or more linking groups.

[0115] In one exemplary embodiment of the present specification, Ar may be an unsubstituted C6 to C60 aryl group or a C6 to C60 aryl group substituted with one or more substituents selected from deuterium, halogen groups, alkyl groups, aryl groups, and heteroaryl groups, or two or more linking groups; or an unsubstituted C2 to C60 heteroaryl group or a C2 to C60 heteroaryl group substituted with one or more substituents selected from deuterium, halogen groups, alkyl groups, aryl groups, and heteroaryl groups, or two or more linking groups.

[0116] In one exemplary embodiment of the present specification, Ar may be an unsubstituted C6 to C30 aryl group or a C6 to C30 aryl group substituted with one or more substituents selected from deuterium, halogen groups, alkyl groups, aryl groups, and heteroaryl groups, or two or more linking groups; or an unsubstituted C2 to C30 heteroaryl group or a C2 to C30 heteroaryl group substituted with one or more substituents selected from deuterium, halogen groups, alkyl groups, aryl groups, and heteroaryl groups, or two or more linking groups.

[0117] In one exemplary embodiment of the present specification, Ar may be an unsubstituted C6 to C60 aryl group or a C6 to C60 aryl group substituted with one or more substituents selected from deuterium, halogen groups, alkyl groups, aryl groups, and heteroaryl groups, or two or more linking groups; or an unsubstituted C2 to C60 heteroaryl group or a C2 to C60 heteroaryl group substituted with one or more substituents selected from deuterium and aryl groups, or two or more linking groups.

[0118] In one exemplary embodiment of the present specification, Ar may be an unsubstituted C6 to C30 aryl group or a C6 to C30 aryl group substituted with one or more substituents selected from deuterium, halogen groups, alkyl groups, aryl groups, and heteroaryl groups, or two or more linking groups; or an unsubstituted C2 to C30 heteroaryl group or a C2 to C30 heteroaryl group substituted with one or more substituents selected from deuterium and aryl groups, or two or more linking groups.

[0119] A linking group means a substituent formed by linking two or more substituents. For example, the linking group of a halogen group and an aryl group may include an aryl group substituted with a halogen group, and the linking group of deuterium, a halogen group, and an aryl group may include an aryl group substituted with deuterium and a halogen group.

[0120] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C1 to C40 haloalkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0121] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 haloalkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0122] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C30 haloalkyl group; or a substituted or unsubstituted C6 to C30 aryl group.

[0123] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C10 haloalkyl group; or a substituted or unsubstituted C6 to C20 aryl group.

[0124] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; -CF 3 ; or a substituted or unsubstituted phenyl group.

[0125] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a C1 to C60 haloalkyl group; or an unsubstituted or deuterium-substituted C6 to C60 aryl group.

[0126] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a C1 to C30 haloalkyl group; or an unsubstituted or deuterium-substituted C6 to C30 aryl group.

[0127] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; a C1 to C10 haloalkyl group; or an unsubstituted or deuterium-substituted C6 to C20 aryl group.

[0128] In one exemplary embodiment of the present specification, R may be hydrogen; deuterium; a halogen group; -CF 3 ; or an unsubstituted or deuterium-substituted phenyl group.

[0129] In one exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-4 below.

[0130] [Chemical Formula 1-1]

[0131]

[0132] [Chemical Formula 1-2]

[0133]

[0134] [Chemical Formula 1-3]

[0135]

[0136] [Chemical Formula 1-4]

[0137]

[0138] In Chemical Formulas 1-1 to 1-4,

[0139] L, Ar, and X are defined in the same way as in Chemical Formula 1,

[0140] H1 is hydrogen; or deuterium,

[0141] Q1 is a halogen group; a substituted or unsubstituted C1-C60 haloalkyl group; or a substituted or unsubstituted C6-C60 aryl group,

[0142] n is an integer from 1 to 9, and when n is 2 or greater, the substituents in the parentheses are the same as or different from each other, and

[0143] o is an integer from 1 to 8, and when o is 2 or greater, the substituents in the parentheses are the same as or different from each other.

[0144] In an exemplary embodiment of the present specification, Q1 can be a halogen group; a substituted or unsubstituted C1-C30 haloalkyl group; or a substituted or unsubstituted C6-C30 aryl group.

[0145] In an exemplary embodiment of the present specification, Q1 can be a halogen group; a substituted or unsubstituted C1-C10 haloalkyl group; or a substituted or unsubstituted C6-C20 aryl group.

[0146] In an exemplary embodiment of the present specification, Q1 can be a halogen group; a C1-C30 haloalkyl group; or an unsubstituted or deuterium-substituted C6-C30 aryl group.

[0147] In an exemplary embodiment of the present specification, Q1 can be a halogen group; a C1-C10 haloalkyl group; or an unsubstituted or deuterium-substituted C6-C20 aryl group.

[0148] In an exemplary embodiment of the present specification, Q1 can be a halogen group; -CF 3 ; or an unsubstituted or deuterium-substituted phenyl group.

[0149] In the two of Chemical Formula 1-3 the substitution positions of Q1 are the same.

[0150] In the two of Chemical Formula 1-4 the substitution positions of Q1 are the same.

[0151] In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-1-1.

[0152] [Chemical Formula 1-1-1]

[0153]

[0154] In Chemical Formula 1-1-1,

[0155] the definitions of L, Ar, and X are the same as those in Chemical Formula 1, and

[0156] each of P1 to P9 is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C60 haloalkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0157] In an exemplary embodiment of the present specification, each of P1 to P9 may be independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C30 haloalkyl group; or a substituted or unsubstituted C6 to C30 aryl group.

[0158] In an exemplary embodiment of the present specification, each of P1 to P9 may be independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C10 haloalkyl group; or a substituted or unsubstituted C6 to C20 aryl group.

[0159] In an exemplary embodiment of the present specification, each of P1 to P9 may be independently hydrogen; deuterium; a halogen group; a C1 to C30 haloalkyl group; or an unsubstituted or deuterium-substituted C6 to C30 aryl group.

[0160] In an exemplary embodiment of the present specification, each of P1 to P9 may be independently hydrogen; deuterium; a halogen group; a C1 to C10 haloalkyl group; or an unsubstituted or deuterium-substituted C6 to C20 aryl group.

[0161] In an exemplary embodiment of the present specification, each of P1 to P9 may be independently hydrogen; deuterium; a halogen group; -CF 3 ; or an unsubstituted or deuterium-substituted phenyl group.

[0162] In an exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 may be 0% to 100%.

[0163] In an exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 may be 0% or 5% to 100%.

[0164] In an exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 may be 0% or 10% to 100%.

[0165] In an exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 may be 0% or 20% to 100%.

[0166] In an exemplary embodiment of the present specification, the deuterium substitution rate of Chemical Formula 1 may be 0% or 30% to 100%.

[0167] In the present specification, the deuterium substitution rate of Chemical Formula 1 means the substitution rate of deuterium relative to the total number of hydrogen atoms and deuterium atoms contained in Chemical Formula 1 above. For example, when Chemical Formula 1 contains 20 hydrogen atoms and 20 deuterium atoms, the substitution rate of 20 deuterium atoms relative to a total of 40 hydrogen atoms and deuterium atoms is 50%.

[0168] In an exemplary embodiment of the present specification, the deuterium substitution rate of the heterocyclic compound of Chemical Formula 1 satisfies the above range, and the photochemical properties of the compound containing deuterium and the compound not containing deuterium are almost similar. However, when deposited on a thin film, the deuterium-containing material tends to stack with a narrower intermolecular distance.

[0169] Therefore, when manufacturing only an electron only device (EOD) and a hole only device (HOD) and determining their current density according to voltage, it can be determined that among the heterocyclic compounds of Chemical Formula 1 of the present invention, the compound containing deuterium exhibits much more balanced charge transport properties than the compound not containing deuterium.

[0170] Furthermore, when observing the surface of the thin film using an atomic force microscope (AFM), it can be determined that the thin film made of the compound containing deuterium is deposited on the surface more uniformly without any aggregated parts.

[0171] Furthermore, since the single bond dissociation energy of carbon and deuterium is higher than that of carbon and hydrogen, among the heterocyclic compounds of Chemical Formula 1 of the present invention, the compound containing deuterium has increased total molecular stability, resulting in the effect of improving the service life of the device.

[0172] In an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following compounds.

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] In addition, various substituents can be introduced into the structure of Chemical Formula 1 to synthesize compounds having the inherent properties of the introduced substituents. For example, materials that meet the requirements of each organic material layer can be synthesized by introducing substituents commonly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials for preparing organic light-emitting devices into the nuclear structure.

[0184] In addition, by introducing various substituents into the structure of Chemical Formula 1, the band gap can be finely adjusted, and at the same time, the properties at the interface between organic materials can be improved and the uses of the materials can be diversified.

[0185] In another exemplary embodiment of the present specification, an organic light-emitting device is provided, which includes: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain one or more heterocyclic compounds of Chemical Formula 1.

[0186] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may contain one or more of the heterocyclic compounds.

[0187] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may contain one of the heterocyclic compounds.

[0188] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains a host, and the host may contain one or more of the heterocyclic compounds.

[0189] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains a host, and the host may contain one of the heterocyclic compounds.

[0190] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains a host, the host includes a green host, and the green host may contain one or more of the heterocyclic compounds.

[0191] In one exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains a host, the host includes a red host, and the red host may contain one or more of the heterocyclic compounds.

[0192] In one exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains a host, the host includes a blue host, and the blue host may contain one or more of the heterocyclic compounds.

[0193] In one exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may contain the heterocyclic compound as an N-type host.

[0194] In one exemplary embodiment of the present specification, the organic material layer containing the heterocyclic compound may further contain a compound of Formula 2 below.

[0195] [Formula 2]

[0196]

[0197] In Formula 2,

[0198] L1 to L3 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene,

[0199] Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl,

[0200] R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C2 to C60 alkenyl; a substituted or unsubstituted C2 to C60 alkynyl; a substituted or unsubstituted C1 to C60 alkoxy; a substituted or unsubstituted C3 to C60 cycloalkyl; a substituted or unsubstituted C2 to C60 heterocycloalkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, or bonded to an adjacent group to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocycle,

[0201] q is an integer from 1 to 3,

[0202] r is an integer from 1 to 4, and

[0203] When q and r are each 2 or greater, the substituents in the parentheses are the same or different from each other.

[0204] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may further contain a compound of Chemical Formula 2.

[0205] In an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer, the light-emitting layer contains a host, and the host may further contain a compound of Chemical Formula 2.

[0206] In an exemplary embodiment of the present specification, the light-emitting layer may further contain a compound of Chemical Formula 2 as a p-type host.

[0207] In an exemplary embodiment of the present specification, L1 to L3 may each independently be a direct bond; or a substituted or unsubstituted C6-C60 arylene group.

[0208] In an exemplary embodiment of the present specification, L1 to L3 may each independently be a direct bond; or a substituted or unsubstituted C6-C40 arylene group.

[0209] In an exemplary embodiment of the present specification, L1 to L3 may each independently be a direct bond; or a substituted or unsubstituted C6-C20 arylene group.

[0210] In an exemplary embodiment of the present specification, L1 to L3 may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0211] In an exemplary embodiment of the present specification, L1 to L3 may each independently be a direct bond; or an unsubstituted or deuterium-substituted C6-C60 arylene group.

[0212] In an exemplary embodiment of the present specification, L1 to L3 may each independently be a direct bond; or an unsubstituted or deuterium-substituted C6-C40 arylene group.

[0213] In an exemplary embodiment of the present specification, L1 to L3 may each independently be a direct bond; or an unsubstituted or deuterium-substituted C6-C20 arylene group.

[0214] In an exemplary embodiment of the present specification, L1 to L3 may each independently be a direct bond; an unsubstituted or deuterium-substituted phenylene group; or an unsubstituted or deuterium-substituted biphenylene group.

[0215] In an exemplary embodiment of the present specification, Ar1 and Ar2 may each independently be a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0216] In one exemplary embodiment of the present specification, Ar1 and Ar2 can each independently be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0217] In one exemplary embodiment of the present specification, Ar1 and Ar2 can each independently be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S.

[0218] In one exemplary embodiment of the present specification, Ar1 and Ar2 can each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0219] In one exemplary embodiment of the present specification, Ar1 and Ar2 can each independently be an unsubstituted or deuterium- and alkyl-substituted one or more substituents of C6-C60 aryl group; or an unsubstituted or deuterium-substituted C2-C60 heteroaryl group.

[0220] In one exemplary embodiment of the present specification, Ar1 and Ar2 can each independently be an unsubstituted or deuterium- and alkyl-substituted one or more substituents of C6-C40 aryl group; or an unsubstituted or deuterium-substituted C2-C40 heteroaryl group.

[0221] In one exemplary embodiment of the present specification, Ar1 and Ar2 can each independently be an unsubstituted or deuterium- and alkyl-substituted one or more substituents of C6-C30 aryl group; or an unsubstituted or deuterium-substituted C2-C30 heteroaryl group.

[0222] In one exemplary embodiment of the present specification, Ar1 and Ar2 can each independently be an unsubstituted or deuterium- and alkyl-substituted one or more substituents of C6-C30 aryl group; or an unsubstituted or deuterium-substituted C2-C30 heteroaryl group containing O or S.

[0223] In one exemplary embodiment of the present specification, Ar1 and Ar2 can each independently be an unsubstituted or deuterium-substituted phenyl group; an unsubstituted or deuterium-substituted biphenyl group; an unsubstituted or deuterium-substituted terphenyl group; an unsubstituted or deuterium-substituted naphthyl group; an unsubstituted or deuterium-substituted phenanthryl group; an unsubstituted or deuterium-substituted dimethylfluorenyl group; an unsubstituted or deuterium-substituted dibenzofuranyl group; or an unsubstituted or deuterium-substituted dibenzothiophenyl group.

[0224] In an exemplary embodiment of the present specification, R11 and R12 can each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or can be bonded to an adjacent group to form a substituted or unsubstituted C6-C60 aromatic ring or a substituted or unsubstituted C2-C60 heterocycle.

[0225] In an exemplary embodiment of the present specification, R11 and R12 can each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or can be bonded to an adjacent group to form a substituted or unsubstituted C6-C60 aromatic ring.

[0226] In an exemplary embodiment of the present specification, R11 and R12 can each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C3-C40 cycloalkyl group; a substituted or unsubstituted C2-C40 heterocycloalkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group, or can be bonded to an adjacent group to form a substituted or unsubstituted C6-C40 aromatic ring or a substituted or unsubstituted C2-C40 heterocycle.

[0227] In an exemplary embodiment of the present specification, R11 and R12 can each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C2-C20 heterocycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or can be bonded to an adjacent group to form a substituted or unsubstituted C6-C20 aromatic ring or a substituted or unsubstituted C2-C20 heterocycle.

[0228] In an exemplary embodiment of the present specification, R11 and R12 can each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C3-C20 cycloalkyl group; a substituted or unsubstituted C2-C20 heterocycloalkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or can be bonded to an adjacent group to form a substituted or unsubstituted C6-C20 aromatic ring.

[0229] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted C6-C60 aromatic ring or a substituted or unsubstituted C2-C60 heterocyclic ring.

[0230] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted C6-C40 aromatic ring or a substituted or unsubstituted C2-C40 heterocyclic ring.

[0231] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted C6-C20 aromatic ring or a substituted or unsubstituted C2-C20 heterocyclic ring.

[0232] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted C6-C20 aromatic ring.

[0233] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

[0234] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing N, or may be bonded to an adjacent group to form a substituted or unsubstituted C6-C20 aromatic ring.

[0235] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing N, or may be bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

[0236] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted carbazolyl group, or may be bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

[0237] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a C6 to C20 aryl group that is unsubstituted or substituted with deuterium or an aryl group; or a C2 to C20 heteroaryl group that is unsubstituted or substituted with deuterium or an aryl group and contains N, or may be bonded to an adjacent group to form an unsubstituted or deuterium-substituted benzene ring.

[0238] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted C6 to C60 aromatic ring.

[0239] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C40 aryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted C6 to C40 aromatic ring.

[0240] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group, or may be bonded to an adjacent group to form a substituted or unsubstituted C6 to C20 aromatic ring.

[0241] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group; or may be bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

[0242] In one exemplary embodiment of the present specification, R11 and R12 may each independently be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group, or may be bonded to an adjacent group to form a substituted or unsubstituted benzene ring.

[0243] In one exemplary embodiment of the present specification, Chemical Formula 2 may be represented by any one of Chemical Formulas 2-1 to 2-4 below.

[0244] [Chemical Formula 2-1]

[0245]

[0246] [Chemical Formula 2-2]

[0247]

[0248] [Chemical Formula 2-3]

[0249]

[0250] [Chemical Formula 2-4]

[0251]

[0252] In Chemical Formulas 2-1 to 2-4,

[0253] L1 to L3, Ar1, Ar2, q, and r are defined in the same manner as in Chemical Formula 2,

[0254] Ar11 is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0255] R21 and R22 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C2-C60 alkenyl group; a substituted or unsubstituted C2-C60 alkynyl group; a substituted or unsubstituted C1-C60 alkoxy group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group,

[0256] s and t are each an integer from 1 to 5,

[0257] u is an integer from 1 to 3, and

[0258] when s, t, and u are each 2 or greater, the substituents in the parentheses are the same as or different from each other.

[0259] In one exemplary embodiment of the present specification, Ar11 may be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0260] In one exemplary embodiment of the present specification, Ar11 may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0261] In one exemplary embodiment of the present specification, Ar11 may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group containing N.

[0262] In an exemplary embodiment of the present specification, Ar11 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted carbazolyl group.

[0263] In an exemplary embodiment of the present specification, Ar11 may be a C6-C30 aryl group that is unsubstituted or substituted with deuterium or an aryl group; or a C2-C30 heteroaryl group that is unsubstituted or substituted with deuterium or an aryl group.

[0264] In an exemplary embodiment of the present specification, Ar11 may be a C6-C20 aryl group that is unsubstituted or substituted with deuterium or an aryl group; or a C2-C20 heteroaryl group that is unsubstituted or substituted with deuterium or an aryl group.

[0265] In an exemplary embodiment of the present specification, Ar11 may be a C6-C20 aryl group that is unsubstituted or substituted with deuterium or an aryl group; or a C2-C20 heteroaryl group that is unsubstituted or substituted with deuterium or an aryl group and contains N.

[0266] In an exemplary embodiment of the present specification, Ar11 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted carbazolyl group.

[0267] In an exemplary embodiment of the present specification, Ar11 may be a C6-C30 aryl group that is substituted or unsubstituted.

[0268] In an exemplary embodiment of the present specification, Ar11 may be a C6-C20 aryl group that is substituted or unsubstituted.

[0269] In an exemplary embodiment of the present specification, Ar11 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0270] In an exemplary embodiment of the present specification, Ar11 may be a C6-C30 aryl group that is unsubstituted or substituted with deuterium or an aryl group.

[0271] In an exemplary embodiment of the present specification, Ar11 may be a C6-C20 aryl group that is unsubstituted or substituted with deuterium or an aryl group.

[0272] In an exemplary embodiment of the present specification, Ar11 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0273] In one exemplary embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0274] In one exemplary embodiment of the present specification, R21 and R22 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; or a substituted or unsubstituted C6-C60 aryl group.

[0275] In one exemplary embodiment of the present specification, R21 and R22 may each independently be hydrogen; or deuterium.

[0276] In one exemplary embodiment of the present specification, Chemical Formula 2 may be selected from the following compounds.

[0277]

[0278]

[0279]

[0280] The organic material layer of the organic light-emitting device of the present invention may be composed of a single-layer structure, but may be composed of a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic material layers.

[0281] In one exemplary embodiment of the present specification, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0282] In another exemplary embodiment of the present specification, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

[0283] The organic light-emitting device according to one exemplary embodiment of the present specification may be manufactured by typical methods and materials for manufacturing an organic light-emitting device, except that a heterocyclic compound of Chemical Formula 1 above is used to form an organic material layer having one or more layers.

[0284] When manufacturing an organic light-emitting device, the heterocyclic compound of Chemical Formula 1 can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. In this document, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0285] In an exemplary embodiment of this specification, the organic light-emitting device can be a blue organic light-emitting device, and the heterocyclic compound of Chemical Formula 1 can be used as a material for a blue organic light-emitting device. For example, the heterocyclic compound of Chemical Formula 1 can be included in the light-emitting layer of the blue organic light-emitting device.

[0286] In another exemplary embodiment of this specification, the organic light-emitting device can be a green organic light-emitting device, and the heterocyclic compound of Chemical Formula 1 can be used as a material for a green organic light-emitting device. For example, the heterocyclic compound of Chemical Formula 1 can be included in the light-emitting layer of the green organic light-emitting device.

[0287] In yet another exemplary embodiment of this specification, the organic light-emitting device can be a red organic light-emitting device, and the heterocyclic compound of Chemical Formula 1 can be used as a material for a red organic light-emitting device. For example, the heterocyclic compound of Chemical Formula 1 can be included in the light-emitting layer of the red organic light-emitting device.

[0288] The organic light-emitting device of the present invention may further include one or more layers selected from the following: a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0289] Figures 1 to 3 The stacking order of the electrodes and the organic material layers of an organic light-emitting device according to an exemplary embodiment of this specification is illustrated. However, the scope of this application is not intended to be limited by these drawings, and the structures of organic light-emitting devices known in the art can also be applied to this application.

[0290] According to Figure 1 , an organic light-emitting device is shown in which a positive electrode 200, an organic material layer 300, and a negative electrode 400 are sequentially stacked on a substrate 100. However, the organic light-emitting device is not limited to such a structure, and as Figure 2 shown, an organic light-emitting device in which a negative electrode, an organic material layer, and a positive electrode are sequentially stacked on a substrate can also be realized.

[0291] Figure 3 The case where the organic material layer is multilayer is illustrated. According to Figure 3The organic light-emitting device includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to the stacking structure described above, and if necessary, other layers except the light-emitting layer can be omitted, and additional necessary functional layers can also be added.

[0292] If necessary, the organic material layer containing the heterocyclic compound of Chemical Formula 1 may additionally contain other materials.

[0293] In the organic light-emitting device according to an exemplary embodiment of the present specification, materials other than the heterocyclic compound of Chemical Formula 1 will be exemplified below, but these materials are merely illustrative and are not intended to limit the scope of the present application, and can be replaced with materials well known in the art.

[0294] As the positive electrode material, a material having a relatively high work function can be used, and a transparent conductive oxide, a metal, a conductive polymer, etc. can be used. Specific examples of the positive electrode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but not limited thereto.

[0295] As the negative electrode material, a material having a relatively low work function can be used, and a metal, a metal oxide, a conductive polymer, etc. can be used. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO 2 / Al; etc., but not limited thereto.

[0296] As the hole injection material, known hole injection materials can also be used, and for example: phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or starburst amine derivatives described in [Advanced Material, 6, page 677 (1994)], such as tris(4-carbazol-9-ylphenyl)amine (TCTA), 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB); polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) which are soluble conductive polymers; polyaniline / camphorsulfonic acid; or polyaniline / poly(4-styrenesulfonate); and so on.

[0297] As the hole transport material, pyrazoline derivatives, arylamine-based derivatives, derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight materials or polymer materials can also be used.

[0298] As the electron transport material, oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, biphenylenequinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. can be used, and low molecular weight materials and polymer materials can also be used.

[0299] As the electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

[0300] As the light-emitting material, materials that emit red, green, or blue light can be used, and if necessary, two or more light-emitting materials can be mixed and used. In this case, two or more light-emitting materials are deposited and used as separate supply sources, or are pre-mixed and deposited and used as one supply source. In addition, fluorescent materials can be used as the light-emitting material, but phosphorescent materials can also be used. As the light-emitting material, materials that emit light by combining holes and electrons injected from the positive electrode and the negative electrode respectively can be used alone, but materials in which the host material and the dopant material participate in light emission together can also be used.

[0301] When the host of the light-emitting material is mixed and used, hosts of the same series can also be mixed and used, and hosts of different series can also be mixed and used. For example, any two or more materials selected from N-type host materials or P-type host materials can be used as the host material for the light-emitting layer.

[0302] Depending on the material to be used, the organic light-emitting device according to an exemplary embodiment of the present specification may be a top-emission type, a bottom-emission type, or a double-emission type.

[0303] Based on principles similar to those applied to organic light-emitting devices, the heterocyclic compound according to an exemplary embodiment of the present specification may function even in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.

[0304] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, the band gap can be finely adjusted, and at the same time, the characteristics at the interface between organic materials can be improved and the uses of the materials can be diversified.

[0305] Another exemplary embodiment of the present specification provides a composition for an organic material layer containing the heterocyclic compound.

[0306] In an exemplary embodiment of the present specification, the composition for the organic material layer may further contain a compound of Chemical Formula 2.

[0307] In an exemplary embodiment of the present specification, the composition for the organic material layer may contain the heterocyclic compound and the compound of Chemical Formula 2 in a weight ratio of 1:10 to 10:1.

[0308] In an exemplary embodiment of the present specification, the composition for the organic material layer may contain the heterocyclic compound and the compound of Chemical Formula 2 in a weight ratio of 1:8 to 8:1, 1:5 to 5:1, or 1:3 to 3:1.

[0309] In an exemplary embodiment of the present specification, the composition for the organic material layer may contain the heterocyclic compound and the compound of Chemical Formula 2 in a weight ratio of 1:1 to 5:1, or 1:1 to 3:1.

[0310] Yet another exemplary embodiment of the present specification provides a method for manufacturing an organic light-emitting device, the method including: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein the formation of the organic material layer includes forming an organic material layer having one or more layers by using the above-described composition for the organic material layer.

[0311] In an exemplary embodiment of the present specification, the formation of the organic material layer may include premixing the composition for the organic layer of the organic light-emitting device to deposit the premixed composition onto a single supply source.

[0312] Pre-mixing means that before depositing the heterocyclic compound of Chemical Formula 1 and the compound of Chemical Formula 2 onto the organic material layer, the materials are first mixed and the mixture is contained in a common container and mixed. Since one deposition source is used during pre-mixing instead of two or more deposition sources, it has the advantage of a more simplified process.

[0313] When pre-mixing is used for the composition of the organic material layer, the deposition conditions (such as the deposition rate) may be significantly affected by the inherent thermal properties of the materials during the deposition of the pre-mixed materials, such that it is necessary to determine the inherent thermal properties of each pre-mixed material. When the thermal properties of the materials are not similar, the deposition process cannot be repeated or reproduced, and a uniform OLED device cannot be manufactured.

[0314] To overcome this problem, the electrical properties of the materials can be controlled by utilizing an appropriate combination of the basic structures and substituents of each material, and at the same time, the thermal properties can also be adjusted according to the form of the molecular structure. The thermal properties of each material can be adjusted to ensure the diversity of various pre-mixed deposition processes between hosts. Thus, not only can two compounds be used as hosts, but also 3 or more types of host materials can be used to ensure the diversity of the pre-mixed deposition process.

[0315] In an exemplary embodiment of the present specification, in addition to the compound of Chemical Formula 2, the composition for the organic material layer may further contain other hosts.

[0316] In an exemplary embodiment of the present specification, the composition for the organic material layer contains the compound of Chemical Formula 2 and may further contain additional hosts.

[0317] Hereinafter, the present specification will be described in more detail by way of examples, but these examples are provided only for illustrating the present application and are not intended to limit the scope of the present application.

[0318] <Preparation Example>

[0319] <Preparation Example 1: Preparation of Compound D-1>

[0320]

[0321] 1) Synthesis of Compound C-1

[0322] Put 3-chloro-2-(2-fluorophenyl)-1-methoxynaphthalene (A-1) (57.4 g, 200 mmol) into a 1000 mL round-bottom flask, create a nitrogen atmosphere, then add DCE (350 mL) thereto, and slowly dropwise add BBr thereto at 0 °C 3(100 g, 38 mL, 400 mmol) for 30 minutes. After stirring at room temperature for 4 hours, the reaction was terminated by adding ice-cold water (200 mL) to the reactants, and then extraction was carried out with MC. The extracted organic solvent was dried over Mg 2 SO 4 and then concentrated. After purification using a silica gel column and methanol, compound C-1 (37.9 g, 150 mmol, 75% yield) was obtained as a white solid.

[0323] 2) Synthesis of compound D-1

[0324] Compound C-1 (37.9 g, 150 mmol), dichlorobis(diphenylphosphino)ferrocene palladium(II) (PdCl 2 (dppf)) (8.6 g, 11.75 mmol), and potassium acetate (KOAc) (44 g, 450 mmol) were placed in a 1000 mL round-bottom flask, a nitrogen atmosphere was created, and then 1,4-d ane (350 mL) was added thereto, and the resulting mixture was stirred at 100 °C for 6 hours. After the reaction temperature was lowered to room temperature, the reaction was terminated by adding water (100 mL) thereto, and then extraction was carried out with dichloromethane (MC). The extracted organic solvent was dried over Mg 2 SO 4 and then concentrated. After recrystallization using a silica gel column and methanol, compound D-1 (48 g, 140 mmol, 93%) was obtained as a white solid.

[0325] <Preparation Example 2> Preparation of compound D-3

[0326]

[0327] 1) Synthesis of compound B-1

[0328] Compound B-1 (50 g, 150 mmol, 73% yield) as a white solid was obtained by carrying out the synthesis in the same manner as in the method for synthesizing compound C-1 in Preparation Example 1, except that compound A-2 was used instead of compound A-1.

[0329] 2) Synthesis of compound C-3

[0330] Compound B-1 (50 g, 150 mmol), phenylboronic acid (X) (222 g, 200 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 )(18.5 g, 7 mmol), and K 2 CO 3(41 g, 300 mmol) was placed in a 1000 mL round-bottom flask and two Alkane (300mL) / H 2 O (60 mL), and the resulting mixture was stirred at 120 ° C for 6 hours. After the reaction was completed, the reaction temperature was lowered to room temperature, and the resulting product was washed with water and then extracted with MC. The extracted organic solvent was purified by Mg 2 SO 4 Dried and then concentrated, silica gel column chromatography and recrystallization were performed to obtain compound C-3 (47 g, 143 mmol, 96%) as a white solid.

[0331] 2) Synthesis of compound D-3

[0332] Compound C-3 (47 g, 143 mmol), PdCl 2 (dppf) (5.23 g, 7.15 mmol) and KOAc (28.06 g, 286 mmol) were placed in a 1000 mL round-bottom flask, a nitrogen atmosphere was created, and then 1,4-dihydroquinone (DPPF) was added thereto. 100 mL) was added, and the resulting mixture was stirred at 100°C for 3 hours. After the reaction temperature was lowered to room temperature, water (100 mL) was added thereto to terminate the reaction, followed by extraction with MC. The extracted organic solvent was purified by MgSO4. 2 SO 4 After drying and then concentrating, compound D-3 (54 g, 129 mmol, 90%) was obtained as a white solid after recrystallization using a silica gel column and methanol.

[0333] <Preparation Example 3> Preparation of Compound C-2

[0334]

[0335] Compound C-1 (20 g, 79 mmol) was placed in a 1000 mL round-bottom flask and dissolved in benzene-D 6 (200mL) solvent, and then set up an ice bath. After slowly dropping trifluoromethanesulfonic acid (TfOH) (49.8mL, 554mmol) thereinto, the resulting mixture was stirred at 60°C for 12 hours. The reaction temperature was lowered to room temperature, an ice bath was set up, distilled water was used for neutralization reaction, and then MC was used for extraction. The extracted organic solvent was passed through Mg 2 SO 4 After drying and then concentration, compound C-2 (20 g, 76.4 mmol, 97%) was obtained as a white solid after purification using methanol.

[0336] <Preparation Example 4> Preparation of the compounds in Table 1

[0337] In the method of Preparation Example 1 or 2, compound A in Table 1 below was used instead of compound A-1 or A-2, and in Preparation Example 2, compound X was used instead of phenylboronic acid. When the core structure contains deuterium, the method of Preparation Example 3 (denoted as +3) was additionally carried out in the steps before preparing compound D to synthesize compounds B to D in Table 1 below.

[0338] [Table 1]

[0339]

[0340]

[0341]

[0342] <Preparation Example 5> Preparation of Compound F-1

[0343]

[0344] Compound D-1 (7.3 g, 21 mmol), 2,4-dichloro-6-phenyl-1,3,5-triazine (E) (2.3 g, 10 mmol), Pd(PPh 3 ) 4 (0.59 g, 0.51 mmol) and K 2 CO 3 (2.81 g, 20.35 mmol) were placed in a 250 mL round-bottom flask, and to this was added di ane (70 mL) / H 2 O (10 mL), and the resulting mixture was stirred at 120 °C for 12 hours. After the reaction was completed, the reaction temperature was lowered to room temperature, and the precipitated solid was filtered. The filtered solid was washed with water, dissolved in chloroform, and then purified using a silica gel column and acetone to obtain compound F-1 (5.2 g, 8.8 mmol, 87%) as a white solid.

[0345] The following target compound F was synthesized by carrying out the synthesis in the same manner as in Preparation Example 5, except that compound D in Table 2 below was used instead of compound D-1 and compound E in Table 2 below was used instead of compound (E).

[0346] [Table 2]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359] <Preparation Example 6> Preparation of Compound G-15

[0360]

[0361] After 7-chloro-5-phenylnaphtho[1,2-b]benzofuran (H) (7 g, 21 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1':4',1”-terphenyl]-4-amine (I) (9 g, 22 mmol), Pd 2 dba 3 (0.97 g, 1 mmol), Xphos (1 g, 2.11 mmol) and 250 ml (4 g, 42 mmol) of NaOtBu were placed in a 500 mL round-bottom flask and dissolved in 150 ml of toluene, and the resulting solution was refluxed for 1 hour. After the reaction was completed, extraction was carried out using MC and distilled water. After concentrating the solvent in the organic layer, the residue was dissolved in MC and purified by silica gel, and then recrystallized using MC / hexane to obtain 12 g (17.4 mmol, 87%) of Compound G-15 as a white solid.

[0362] The following target compound G was synthesized by carrying out the synthesis in the same manner as in Preparation Example 6, except that the compounds H and I in Table 3 below were used instead of the compounds (H) and (I) in Preparation Example 6, respectively.

[0363] [Table 3]

[0364]

[0365] By FD mass spectrometry and 1It was determined by 1H-NMR that the compounds synthesized in Preparation Examples 1 to 6 were synthesized as the desired compounds. The values measured by field desorption mass spectrometry (FD-Mass) are shown in Table 4 below, and the values measured by 1 1H NMR (CDCl 3 , 200 MHz) are shown in Table 5 below.

[0366] [Table 4]

[0367]

[0368]

[0369] [Table 5]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375] [Experimental Example]

[0376] [Experimental Example 1]

[0377] (1) Fabrication of organic light-emitting device

[0378] A glass substrate thinly coated with indium tin oxide (ITO) to have a thickness was ultrasonically washed with distilled water. When the washing with distilled water was completed, the glass substrate was ultrasonically washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then subjected to ultraviolet ozone (UVO) treatment for 5 minutes using UV in a UV washer. Thereafter, the substrate was transferred to a plasma washer (PT), and then subjected to plasma treatment in a vacuum state for the ITO work function and for removing the residual film, and transferred to a thermal deposition apparatus for organic deposition.

[0379] A hole injection layer of 4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) and a hole transport layer of N,N′-di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine (NPB) were formed as a common layer on the ITO transparent electrode (positive electrode).

[0380] The light-emitting layer was thermally vacuum-deposited thereon as follows. By using one type of compound described in Table 6 below as a red host, and using (piq) 2(Ir)(acac) is used as a red phosphorescent dopant and is incorporated in an amount of 3% into (piq) 2 (Ir)(acac)-doped host to deposit a light-emitting layer to have a thickness of. Thereafter, BCP is deposited as a hole-blocking layer to have a thickness of, and Alq is deposited thereon as an electron-transporting layer 3 to have a thickness of. Thereafter, BCP is deposited as a hole-blocking layer to have a thickness of, and Alq is deposited thereon as an electron-transporting layer 3 to have a thickness of. Finally, lithium fluoride (LiF) is deposited on the electron-transporting layer to have a thickness of to form an electron-injection layer, and then aluminum (Al) is deposited on the electron-injection layer as a negative electrode to have a thickness of to form a negative electrode, thereby fabricating an organic electroluminescent device.

[0381] Compounds X1 to X15 used in Table 6 below are as follows.

[0382]

[0383] Meanwhile, for each material, all the organic compounds required for fabricating the OLED device are subjected to vacuum sublimation purification under 10 -8 torr to 10 -6 torr and are used for fabricating the OLED.

[0384] (2) Measurement of driving voltage, luminous efficiency, and service life of the organic light-emitting device

[0385] For the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics are measured by M7000 manufactured by McScience Inc., and based on the measurement results, at a reference luminance of 6,000 cd / m 2 , the T is measured by a service life measurement device (M6000) manufactured by McScience Inc. 90 . T 90 means the service life (unit: hours), which is the time taken for the luminance to reach 90% of the initial luminance.

[0386] The characteristics of the above-fabricated organic electroluminescent device are shown in Table 6 below.

[0387] [Table 6]

[0388]

[0389]

[0390]

[0391]

[0392] The heterocyclic compound of Chemical Formula 1 of the present invention has high thermal stability, an appropriate molecular weight, and a band gap. The appropriate band gap of the light-emitting layer prevents the loss of electrons and holes, helping to effectively form a recombination region.

[0393] As can be seen from the results in Table 6, it can be determined that the organic light-emitting device using the heterocyclic compound represented by Chemical Formula 1 of the present invention exhibits improved performance compared to the organic light-emitting devices using Comparative Compounds X1 to X15.

[0394] Specifically, compared with Comparative Examples 1 to 9, 14, and 15, the example group of the present invention shows excellent results, especially in terms of luminous efficiency and service life. This is considered to be due to the fact that when a substituent is substituted at the 6-position of the naphtho[1,2-b]benzofuran nucleus as in Chemical Formula 1 of the present invention, the example group of the present invention has a higher hole mobility due to a deeper HOMO value compared to the compounds substituted at other positions. In addition, Comparative Examples 10 to 13 have an asymmetric structure, which is considered to reduce the conjugated region of the molecule and thus lower the electron mobility, resulting in a lower efficiency than that of the chemical formula of the present invention.

[0395] <Experimental Example 2>

[0396] (1) Fabrication of organic light-emitting device

[0397] An organic light-emitting device was fabricated in the same manner as in Experimental Example 1, except that two compounds shown in Table 7 below were used instead of one compound shown in Table 6 above as the red host of the light-emitting layer.

[0398] (2) Measurement of driving voltage, luminous efficiency, and service life of organic light-emitting device

[0399] For the organic electroluminescent device fabricated as described above, the electroluminescent (EL) characteristics were measured by M7000 manufactured by McScience Inc., and based on the measurement results, at a reference luminance of 6,000 cd / m 2 2, the T 90 was measured by a service life measurement device (M6000) manufactured by McScience Inc. 90 T

[0400] The characteristics of the above-manufactured organic electroluminescent device are shown in Table 7 below.

[0401] [Table 7]

[0402]

[0403]

[0404] As can be seen from the results of Table 6 and Table 7 above, when the heterocyclic compound of the present invention and the compound of Chemical Formula 2 are combined and used in the light-emitting layer of an organic light-emitting device, improved driving voltage, efficiency, and service life characteristics are shown compared to when the compound is used as a single compound. This corresponds to the result that by using both the heterocyclic compound of Chemical Formula 1 of the present invention and the compound of Chemical Formula 2 of the present invention in the light-emitting layer of an organic light-emitting device, an acceptor (n-host) having good electron transport ability and a donor (p-host) having good hole transport ability can be used as the host of the light-emitting layer to reduce the driving voltage for injecting electrons and holes, and to improve the efficiency and service life by effectively forming a recombination region.

Claims

1. A heterocyclic compound of the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, X is O or S, L is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R is hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C1 to C60 haloalkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and m is an integer of 1 to 9, and when m is 2 or greater, the substituents in the brackets are the same as or different from each other.

2. The heterocyclic compound according to claim 1, wherein compound 1 is represented by the following chemical formula 1-0 or chemical formula 1-S: [Chemical formula 1-O] [Chemical formula 1-S] In Chemical Formula 1-O and Chemical Formula 1-S, The definitions of each substituent are the same as those in Chemical Formula 1.

3. The heterocyclic compound according to claim 1, wherein Ar is a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

4. The heterocyclic compound according to claim 1, wherein R is hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1 to C30 haloalkyl group; or a substituted or unsubstituted C6 to C30 aryl group. 5 . The heterocyclic compound according to claim 1 , wherein the deuterium substitution rate of Chemical Formula 1 is 0%, or 5% to 100%.

6. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

7. An organic light-emitting device, comprising: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprises one or more of the heterocyclic compounds according to any one of claims 1 to 6. 8 . The organic light emitting device according to claim 7 , wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises one or more of the heterocyclic compounds. 9 . The organic light-emitting device according to claim 8 , wherein the light-emitting layer comprises a host, and the host comprises one or more of the heterocyclic compounds.

10. The organic light emitting device according to claim 7, wherein the organic material layer comprising the heterocyclic compound further comprises a compound of the following Chemical Formula 2: [Chemical formula 2] In chemical formula 2, L1 to L3 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or are bonded to an adjacent group to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, q is an integer from 1 to 3, r is an integer from 1 to 4, and When q and r are each 2 or greater, the substituents in the brackets are the same as or different from each other.

11. The organic light emitting device according to claim 10, wherein Chemical Formula 2 is selected from the following compounds: 12 . A composition for an organic material layer of an organic light-emitting device, the composition comprising the heterocyclic compound according to claim 1 .

13. The composition according to claim 12, further comprising a compound of the following Chemical Formula 2: [Chemical formula 2] In chemical formula 2, L1 to L3 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar1 and Ar2 are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R11 and R12 are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or are bonded to an adjacent group to form a substituted or unsubstituted C6 to C60 aromatic ring or a substituted or unsubstituted C2 to C60 heterocyclic ring, q is an integer from 1 to 3, r is an integer from 1 to 4, and When q and r are each 2 or greater, the substituents in the brackets are the same as or different from each other.

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