Organic light-emitting device, method for manufacturing the same, and composition for organic material layer of organic light-emitting device

Abstract

This specification relates to an organic light-emitting device, a method for manufacturing the same, and a composition for an organic material layer.

Description

Technical Field

[0001] This application claims priority and benefit of Korean Patent Application No. 10-2019-0124527, filed with the Korean Intellectual Property Office on October 8, 2019, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to an organic light emitting device, a method for manufacturing the same, and a composition for an organic material layer of an organic light emitting device. Background Art

[0003] An electroluminescent device is a type of self-luminous display device and has advantages such as a wide viewing angle, a high response speed, and excellent contrast.

[0004] 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 such a structure, electrons and holes injected from the two electrodes combine and pair in the organic thin film, and light is emitted as these annihilate. If necessary, the organic thin film may be formed as a single layer or multiple layers.

[0005] The material of the organic thin film may have a light emitting function if necessary. For example, as the material of the organic thin film, a compound capable of forming a light emitting layer alone by itself may be used, or a compound capable of acting as a host or a dopant of a host-dopant based light emitting layer may also be used. In addition, a compound capable of acting as a hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. may be used as the material of the organic thin film.

[0006] There is a continuous need to develop organic thin film materials to improve the performance, lifespan, or efficiency of organic light emitting devices.

[0007] <Prior Art Documents>

[0008] (Patent Document 1) U.S. Patent No. 4,356,429 Summary of the Invention

[0009] Technical Problem

[0010] This application relates to providing an organic light emitting device, a method for manufacturing the same, and a composition for an organic material layer of an organic light emitting device.

[0011] Technical Solution

[0012] One embodiment of this application provides an organic light emitting device including: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode,

[0013] One or more layers in the organic material layer contain a heterocyclic compound represented by Chemical Formula 1 below and a heterocyclic compound represented by Chemical Formula 2 below.

[0014] [Chemical Formula 1]

[0015]

[0016] [Chemical Formula 2]

[0017]

[0018] In Chemical Formulas 1 and 2,

[0019] N-Het is a substituted or unsubstituted monocyclic or polycyclic C2-C60 heterocyclic group containing one or more N's,

[0020] L and L1 are a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene,

[0021] Ar1 is a substituted or unsubstituted C6-C60 aryl group, or is represented by Chemical Formula 1-A below,

[0022] [Chemical Formula 1-A]

[0023]

[0024] X1 is O; S; or NR22,

[0025] R1 to R4 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6-C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 heterocyclic ring,

[0026] R5 to R7 and R11 to R19 are the same as or different from each other, and are each independently selected from: hydrogen; deuterium; halogen; cyano; 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; a substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and -NRR',

[0027] A1 and A2 are the same as or different from each other, and each independently is O; S; NRa; or CRbRc,

[0028] R22, R, R', R'', and Ra to Rc are the same as or different from each other, and each independently is hydrogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl,

[0029] b, c, and d are integers from 0 to 3,

[0030] f is an integer from 0 to 2, and

[0031] a and e are integers from 0 to 5.

[0032] In addition, another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, the composition comprising a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0033] Finally, an embodiment of the present application provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material 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 one or more organic material layers using the composition for an organic material layer according to an embodiment of the present application.

[0034] Advantageous Effects

[0035] The heterocyclic compound according to an embodiment of the present application can be used as a material for an organic material layer of an organic light-emitting device. The heterocyclic compound can be used as a material for a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. in an organic light-emitting device. In particular, the heterocyclic compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be used as materials for an organic material layer of an organic light-emitting device. In addition, when the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are used in an organic light-emitting device, the driving voltage of the device can be reduced, the light efficiency can be improved, and the lifetime characteristics of the device can be improved through the thermal stability of the compounds.

[0036] In particular, the compound of Chemical Formula 1 has a more electronically stable structure through the 3-position of the benzene ring on the side of the dibenzofuran structure substituted with an N-containing ring and the other benzene ring of the dibenzofuran structure substituted with a specific substituent without being substituted with an N-containing ring, which provides appropriate energy levels and thermal stability. By using the compound of Chemical Formula 1, an organic light-emitting device with improved lifetime, driving stability, and efficiency can be manufactured. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] Figures 1 to 3 are diagrams each schematically showing the laminated structure of an organic light-emitting device according to an embodiment of the present application.

[0038] Figure 4 and Figure 5 is a diagram showing the thermal stability of Compound 2-19 of the present application.

[0039] Figure 6 and Figure 7 is a diagram showing the thermal stability of Compound 2-20 of the present application.

[0040] Figure 8 and Figure 9 is a diagram showing the thermal stability of Compound 2-22 of the present application.

[0041] Figure 10 and Figure 11 is a diagram showing the thermal stability of Compound 2-8 of the present application.

[0042] Figure 12 and Figure 13 is a diagram showing the thermal stability of Compound 2-18 of the present application.

[0043] Figure 14 and Figure 15 is a diagram showing the thermal stability of Compound 2-79 of the present application.

[0044] Figure 16 and Figure 17 is a diagram showing the thermal stability of Compound 2-123 of the present application.

[0045] Figure 18 and Figure 19 is a diagram showing the thermal stability of Compound A.

[0046] Figure 20 and Figure 21 is a diagram showing the thermal stability of Compound C.

[0047] <REFERENCE NUMERALS>

[0048] 100: Substrate

[0049] 200: Anode

[0050] 300: Organic material layer

[0051] 301: Hole injection layer

[0052] 302: Hole transport layer

[0053] 303: Light-emitting layer

[0054] 304: Hole blocking layer

[0055] 305: Electron transport layer

[0056] 306: Electron injection layer

[0057] 400: Cathode Detailed implementation manners

[0058] In the following, the present application will be described in detail.

[0059] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and there is no limitation on the substitution position as long as it is a position where a hydrogen atom is substituted (i.e., a position where a substituent can substitute), and when two or more substituents are substituted, these two or more substituents may be the same or different from each other.

[0060] In this specification, "in the case where no substituent is indicated in a chemical formula or a compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( 2 H) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0061] In one embodiment of the present application, "in the case where no substituent is indicated in a chemical formula or a compound structure" may mean that all positions that can appear as substituents may be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and here, the content of deuterium may be from 0% to 100%.

[0062] In one embodiment of the present application, in the case of "in the case where no substituent is indicated in a chemical formula or a compound structure", when deuterium is not explicitly excluded (for example, the deuterium content is 0% or the hydrogen content is 100%), hydrogen and deuterium may be mixed in the compound. In other words, different from the case where the hydrogen content is 100% or the deuterium content is 0%, the expression "substituent X is hydrogen" does not exclude deuterium, and thus may mean a state in which hydrogen and deuterium are mixed.

[0063] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, is an element having a deuteron formed by one proton and one neutron as a nucleus, and can be represented as hydrogen-2, and the element symbol can also be written as D or 2 H.

[0064] In one embodiment of the present application, an isotope means an atom having the same atomic number (Z) but having a different mass number (A), and can also be interpreted as an element having the same number of protons but having a different number of neutrons.

[0065] In one embodiment of the present application, when the total number of substituents that an alkaline compound can have is defined as T1, and the number of a specific substituent among these is defined as T2, the meaning of the content T% of the specific substituent can be defined as T2 / T1×100 = T%.

[0066] In other words, in one example, A phenyl group represented by having a deuterium content of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and the number of deuteriums among these is 1 (T2 in the formula). In other words, a phenyl group having a deuterium content of 20% can be represented by the following structural formula.

[0067]

[0068] Furthermore, in one embodiment of the present application, a "phenyl group with a deuterium content of 0%" can mean a phenyl group that does not contain deuterium atoms, that is, a phenyl group having 5 hydrogen atoms.

[0069] In this specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the following: C1 to C60 linear or branched alkyl groups; C2 to C60 linear or branched alkenyl groups; C2 to C60 linear or branched alkynyl groups; C3 to C60 monocyclic or polycyclic cycloalkyl groups; C2 to C60 monocyclic or polycyclic heterocycloalkyl groups; C6 to C60 monocyclic or polycyclic aryl groups; C2 to C60 monocyclic or polycyclic heteroaryl groups; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamines; C6 to C60 monocyclic or polycyclic arylamines; and C2 to C60 monocyclic or polycyclic heteroarylamines, or is unsubstituted, or substituted with substituents connected by two or more substituents selected from the substituents shown above, or is unsubstituted.

[0070] In one embodiment of the present application, R, R' and R" are the same as or different from each other, and can each independently be hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0071] In this specification, the halogen can be fluorine, chlorine, bromine or iodine.

[0072] In this specification, alkyl includes linear or branched alkyl groups having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkyl group can be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof may 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, cyclopentylmethyl, cyclohexylmethyl, 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.

[0073] In this specification, alkenyl includes linear or branched alkenyl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof may 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, stilbenyl, styryl, etc., but are not limited thereto.

[0074] In this specification, alkynyl includes linear or branched alkynyl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0075] In this specification, alkoxy can be linear, branched or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0076] In this specification, cycloalkyl includes monocyclic or polycyclic cycloalkyl having 3 to 60 carbon atoms and may be further substituted with other substituents. Herein, polycyclic means a group in which cycloalkyl is directly linked to or fused with other cyclic groups. Herein, the other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl, and heteroaryl. The number of carbon atoms in cycloalkyl may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples thereof may 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.

[0077] In this specification, heterocycloalkyl contains O, S, Se, N, or Si as heteroatoms and includes monocyclic or polycyclic heterocycloalkyl having 2 to 60 carbon atoms and may be further substituted with other substituents. Herein, polycyclic means a group in which heterocycloalkyl is directly linked to or fused with other cyclic groups. Herein, the other cyclic groups may be heterocycloalkyl, but may also be different types of cyclic groups, such as cycloalkyl, aryl, and heteroaryl. The number of carbon atoms in heterocycloalkyl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0078] In this specification, aryl includes monocyclic or polycyclic aryl having 6 to 60 carbon atoms and may be further substituted with other substituents. Herein, polycyclic means a group in which aryl is directly linked to or fused with other cyclic groups. Herein, the other cyclic groups may be aryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl includes spiro groups. The number of carbon atoms in aryl may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of aryl may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, fluorenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylene, phenalene, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, its fused ring groups, etc., but are not limited thereto.

[0079] In this specification, fluorenyl may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0080] When fluorenyl is substituted, it may include the following structures, however, the structures are not limited thereto.

[0081]

[0082] In this specification, heteroaryl includes S, O, Se, N or Si as heteroatoms, including monocyclic or polycyclic heteroaryl with 2 to 60 carbon atoms, and can be further substituted by other substituents. Here, polycyclic means that heteroaryl is directly connected to other cyclic groups or is fused with other cyclic groups. Here, other cyclic groups can be heteroaryl, but can also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and aryl. The number of carbon atoms of heteroaryl can be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl can include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furyl, thiophene (thiophene group), imidazolyl, pyrazolyl, Azolyl, iso Azolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, Azine, thiazine, di Indole, triazine, tetrazine, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, quinazolinyl, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, naphthyridinyl, triazaindenyl, indolyl, indolizinyl, benzothiazolyl, benzo oxazolyl, benzimidazolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzothiophenyl, spirobis(dibenzothiophenyl), dihydrophenazinyl, phenazinyl, azine, phenanthridinyl, imidazopyridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, dihydroindole, 10,11-dihydro-dibenzo[b,f]azepine The invention also includes 9,10-dihydroacridinyl, phenanthrazinyl group, phenothiazinyl group, phthalazinyl, naphthyridinyl, phenanthroline, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrobenzo[b,e][1,4]azasilyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindole, 5,11-dihydroindeno[1,2-b]carbazolyl, etc., but is not limited thereto.

[0083] In this specification, the amino group may be selected from monoalkylamino; monoarylamino; monoheteroarylamino; -NH2; dialkylamino; diarylamino; diheteroarylamino; alkylarylamino; alkylheteroarylamino; and arylheteroarylamino, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples of the amino group may 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.

[0084] In this specification, arylene means an aryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied to arylene, except that arylene is each a divalent group. In addition, heteroarylene means a heteroaryl group having two bonding sites, that is, a divalent group. The description of the heteroaryl group provided above can be applied to heteroarylene, except that heteroarylene is each a divalent group.

[0085] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 are the same as or different from each other, and may each independently be a substituent formed from at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specifically, the phosphine oxide group may be substituted with an aryl group, and as the aryl group, the examples described above can be used. Examples of the phosphine oxide may include diphenylphosphine oxide group, dinaphthylphosphine oxide group, etc., but are not limited thereto.

[0086] In this specification, the silyl group is a substituent containing Si and having an Si atom directly connected as a group, and is represented by -SiR104R105R106. R104 to R106 are the same as or different from each other, and may each independently be a substituent formed from at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0087] In this specification, an "adjacent" group may mean a substituent that replaces an atom directly linked to the atom substituted by the corresponding substituent, a substituent located spatially closest to the corresponding substituent, or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents replacing ortho positions in a benzene ring and two substituents replacing the same carbon in an aliphatic ring may be construed as groups "adjacent" to each other.

[0088] As the aliphatic or aromatic hydrocarbon ring or heterocyclic ring that can be formed by adjacent groups, structures exemplified as the above cycloalkyl, cycloheteroalkyl, aryl, and heteroaryl can be used, with the difference that the aliphatic or aromatic hydrocarbon ring or heterocyclic ring that can be formed by adjacent groups is not a monovalent group.

[0089] One embodiment of the present application provides an organic light-emitting device including: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0090] In one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3 to 6.

[0091] [Chemical Formula 3]

[0092]

[0093] [Chemical Formula 4]

[0094]

[0095] [Chemical Formula 5]

[0096]

[0097] [Chemical Formula 6]

[0098]

[0099] In Chemical Formulas 3 to 6, N-Het, L, L1, R1 to R7, X1, and a to e have the same definitions as in Chemical Formula 1.

[0100] In one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3-1 to 6-1.

[0101] [Chemical Formula 3-1]

[0102]

[0103] [Chemical Formula 4-1]

[0104]

[0105] [Chemical Formula 5-1]

[0106]

[0107] [Chemical Formula 6-1]

[0108]

[0109] In Chemical Formulas 3-1 to 6-1, N-Het, L, L1, R6, R7, a to c, and e have the same definitions as in Chemical Formula 1, and

[0110] Ar2 is a substituted or unsubstituted monocyclic or polycyclic C6 to C60 aryl group.

[0111] As in the compounds of Chemical Formula 1 according to the present application, when the 3-position of dibenzofuran is used, the linearity of the whole material increases, which is effective in increasing the stability of the whole structure. This is the effect obtained for azine-based compounds with substituents having a strong electron-withdrawing tendency. In particular, when substituted with triazine, the dibenzofuran at the center of the structure remains electron-deficient, which requires more electrical energy (electrons) to break the bonds. Here, as the linearity of the material is higher, the electron-withdrawing ability is stronger, and when the electrons in the molecule are concentrated around the triazine structure, the effect of further increasing the electron deficiency of the whole structure is obtained. Therefore, when driving the device, the effect of preventing the host material from being decomposed by current is obtained.

[0112] In one embodiment of the present application, Ar1 is a substituted or unsubstituted C6 to C60 aryl group, or can be represented by Chemical Formula 1-A.

[0113] In another embodiment, Ar1 is a substituted or unsubstituted C6 to C40 aryl group, or can be represented by Chemical Formula 1-A.

[0114] In another embodiment, Ar1 is a C6 to C40 aryl group, or can be represented by Chemical Formula 1-A.

[0115] In another embodiment, Ar1 is a C6 to C20 aryl group, or can be represented by Chemical Formula 1-A.

[0116] In another embodiment, Ar1 is a C10 to C20 aryl group, or can be represented by Chemical Formula 1-A.

[0117] In another embodiment, Ar1 is a C6 aryl group, or can be represented by Chemical Formula 1-A.

[0118] In another embodiment, Ar1 is phenyl; biphenyl; terphenyl; or triphenylene, or can be represented by Chemical Formula 1-A.

[0119] In one embodiment of the present application, Ar2 is a substituted or unsubstituted monocyclic or polycyclic C6-C60 aryl group.

[0120] In another embodiment, Ar2 is a substituted or unsubstituted monocyclic or polycyclic C6-C40 aryl group.

[0121] In another embodiment, Ar2 is a substituted or unsubstituted monocyclic to tetracyclic C6-C40 aryl group.

[0122] In another embodiment, Ar2 is a substituted or unsubstituted monocyclic to pentacyclic C6-C40 aryl group.

[0123] In another embodiment, Ar2 is a substituted or unsubstituted monocyclic C6-C20 aryl group.

[0124] In another embodiment, Ar2 is a substituted or unsubstituted bicyclic C6-C20 aryl group.

[0125] In another embodiment, Ar2 is a substituted or unsubstituted tricyclic C6-C30 aryl group.

[0126] In another embodiment, Ar2 is a substituted or unsubstituted tetracyclic C6-C40 aryl group.

[0127] In another embodiment, Ar2 is a C6-C40 aryl group.

[0128] In another embodiment, Ar2 is a C6-C20 aryl group.

[0129] In another embodiment, Ar2 is a C10-C20 aryl group.

[0130] In another embodiment, Ar2 is a C6 aryl group.

[0131] In another embodiment, Ar2 can be phenyl; biphenyl; terphenyl; or triphenylene.

[0132] In one embodiment of the present application, R5 to R7 are the same as or different from each other, and each can independently be selected from hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C2-C60 alkenyl; substituted or unsubstituted C2-C60 alkynyl; substituted or unsubstituted C1-C60 alkoxy; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; substituted or unsubstituted C2-C60 heteroaryl; -P(=O)RR'; -SiRR'R"; and -NRR'.

[0133] In another embodiment, R5 to R7 are the same as or different from each other, and each can independently be selected from hydrogen; halogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; substituted or unsubstituted C2-C60 heteroaryl; -P(=O)RR'; -SiRR'R"; and -NRR'.

[0134] In another embodiment, R5 to R7 are the same as or different from each other, and each can independently be selected from hydrogen; halogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C40 aryl; substituted or unsubstituted C2-C40 heteroaryl; -P(=O)RR'; -SiRR'R"; and -NRR'.

[0135] In another embodiment, R5 to R7 can be hydrogen.

[0136] In another embodiment, R5 can be hydrogen.

[0137] In another embodiment, R6 can be hydrogen.

[0138] In another embodiment, R7 can be hydrogen.

[0139] In one embodiment of the present application, L can be a direct bond; substituted or unsubstituted C6-C60 arylene; or substituted or unsubstituted C2-C60 heteroarylene.

[0140] In another embodiment, L can be a direct bond; substituted or unsubstituted C6-C40 arylene; or substituted or unsubstituted C2-C40 heteroarylene.

[0141] In another embodiment, L can be a direct bond; substituted or unsubstituted C6-C40 monocyclic or polycyclic arylene; or substituted or unsubstituted C2-C40 heteroarylene.

[0142] In another embodiment, L can be a direct bond; a substituted or unsubstituted C6-C40 monocyclic arylene; or a substituted or unsubstituted C10-C40 polycyclic arylene.

[0143] In another embodiment, L can be a direct bond; a C6-C40 monocyclic arylene; or a C10-C40 polycyclic arylene.

[0144] In another embodiment, L can be a direct bond; phenylene; biphenylene; or naphthylene.

[0145] In another embodiment, L can be a direct bond.

[0146] In one embodiment of the present application, L1 can be a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene.

[0147] In another embodiment, L1 can be a direct bond; a substituted or unsubstituted C6-C40 arylene; or a substituted or unsubstituted C2-C40 heteroarylene.

[0148] In another embodiment, L1 can be a direct bond; a substituted or unsubstituted C6-C40 monocyclic or polycyclic arylene; or a substituted or unsubstituted C2-C40 heteroarylene.

[0149] In another embodiment, L1 can be a direct bond; a substituted or unsubstituted C6-C40 monocyclic arylene; or a substituted or unsubstituted C10-C40 polycyclic arylene.

[0150] In another embodiment, L1 can be a direct bond; a C6-C40 monocyclic arylene; or a C10-C40 polycyclic arylene.

[0151] In another embodiment, L1 can be a direct bond; phenylene; biphenylene; or naphthylene.

[0152] In one embodiment of the present application, R1 to R4 are the same as or different from each other, and each independently is hydrogen; a substituted or unsubstituted C1-C60 alkyl; a substituted or unsubstituted C6-C60 aryl; or a substituted or unsubstituted C2-C60 heteroaryl, or two or more adjacent groups can be bonded to each other to form a substituted or unsubstituted C6-C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2-C60 heterocycle.

[0153] In another embodiment, R1 to R4 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl, or two or more adjacent groups can bond to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring.

[0154] In another embodiment, R1 to R4 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted C1-C40 alkyl; substituted or unsubstituted C6-C40 aryl; or substituted or unsubstituted C2-C40 heteroaryl, or two or more adjacent groups can bond to each other to form a substituted or unsubstituted C6-C40 aromatic hydrocarbon ring.

[0155] In another embodiment, R1 to R4 are the same as or different from each other and are each independently hydrogen; C1-C40 alkyl; C6-C40 aryl; or C2-C40 heteroaryl, or two or more adjacent groups can bond to each other to form a C6-C40 aromatic hydrocarbon ring.

[0156] In another embodiment, R1 to R4 are the same as or different from each other and are each independently hydrogen; C6-C40 monocyclic aryl; or C10-C40 polycyclic aryl, or two or more adjacent groups can bond to each other to form a C6-C40 monocyclic aromatic hydrocarbon ring.

[0157] In another embodiment, R1 to R4 are the same as or different from each other and are each independently hydrogen; phenyl; biphenyl; or triphenylene, or two or more adjacent groups can bond to each other to form a benzene ring.

[0158] In one embodiment of the present application, X1 can be O; S; or NR22.

[0159] In one embodiment of the present application, X1 can be O.

[0160] In one embodiment of the present application, X1 can be S.

[0161] In one embodiment of the present application, X1 can be NR22.

[0162] In one embodiment of the present application, R22 can be substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

[0163] In another embodiment, R22 can be a C1 to C60 alkyl group; a C6 to C60 aryl group; or a C2 to C60 heteroaryl group.

[0164] In another embodiment, R22 can be a C6 to C60 aryl group.

[0165] In another embodiment, R22 can be a C6 to C40 monocyclic aryl group.

[0166] In another embodiment, R22 can be a phenyl group.

[0167] In one embodiment of the present application, Formula 1-A can be represented by any one of the following Formulas 1-1 to 1-6.

[0168] [Formula 1-1]

[0169]

[0170] [Formula 1-2]

[0171]

[0172] [Formula 1-3]

[0173]

[0174] [Formula 1-4]

[0175]

[0176] [Formula 1-5]

[0177]

[0178] [Formula 1-6]

[0179]

[0180] In Formulas 1-1 to 1-6,

[0181] X1, R5, and d have the same definitions as in Formula 1-A,

[0182] which means the position connected to L1 of Formula 1,

[0183] R31 to R34 are the same as or different from each other, and each independently is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0184] R35 and R36 are the same as or different from each other, and each independently is hydrogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

[0185] In one embodiment of the present application, R31 to R34 are the same as or different from each other, and each may independently be substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

[0186] In another embodiment, R31 to R34 are the same as or different from each other, and each may independently be substituted or unsubstituted C6-C60 aryl.

[0187] In another embodiment, R31 to R34 are the same as or different from each other, and each may independently be substituted or unsubstituted C6-C40 aryl.

[0188] In another embodiment, R31 to R34 are the same as or different from each other, and each may independently be substituted or unsubstituted C6-C40 monocyclic or polycyclic aryl.

[0189] In another embodiment, R31 to R34 are the same as or different from each other, and each may independently be C6-C40 monocyclic aryl; or C10-C40 polycyclic aryl.

[0190] In another embodiment, R31 to R34 are the same as or different from each other, and each may independently be phenyl; or triphenylene.

[0191] In one embodiment of the present application, R35 and R36 may be hydrogen.

[0192] In one embodiment of the present application, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2-C60 heterocyclic group containing one or more Ns.

[0193] In another embodiment, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2-C60 heterocyclic group containing one or more and three or fewer Ns.

[0194] In another embodiment, N-Het may be a substituted or unsubstituted monocyclic C2-C60 heterocyclic group containing one or more and three or fewer Ns.

[0195] In another embodiment, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2-C40 heterocyclic group containing one or more and three or fewer Ns.

[0196] In another embodiment, N-Het can be a substituted or unsubstituted monocyclic C2-C40 heterocyclic group containing one or more and three or fewer N atoms.

[0197] In another embodiment, N-Het can be a monocyclic C2-C40 heterocyclic group that is unsubstituted or substituted with one or more substituents selected from C1-C20 alkyl, C6-C40 aryl, C2-C40 heteroaryl, -P(=)ORR', and -SiRR'R", or a substituent in which two or more of the substituents are linked, and contains one or more and three or fewer N atoms.

[0198] In another embodiment, N-Het can be a pyridyl, pyrimidinyl, or triazinyl group that is unsubstituted or substituted with one or more substituents selected from C1-C20 alkyl, C6-C40 aryl, C2-C40 heteroaryl, -P(=)ORR', and -SiRR'R", or a substituent in which two or more of the substituents are linked.

[0199] In another embodiment, N-Het can be a pyridyl group that is unsubstituted or substituted with a phenyl group; a pyrimidinyl group that is unsubstituted or substituted with a phenyl group; or a triazinyl group that is unsubstituted or substituted with one or more substituents selected from the following: a phenyl group that is unsubstituted or substituted with triphenylene, diphenylfluorene, -P(=)ORR', or -SiRR'R", biphenyl, dibenzofuran, dimethylfluorene, and dibenzothiophene.

[0200] In one embodiment of the present application, N-Het can be selected from the following structural formulas.

[0201]

[0202] In the structural formula,

[0203] means the position connected to L of Chemical Formula 1, and

[0204] R41 to R45 are the same as or different from each other, and each independently is hydrogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

[0205] In another embodiment, R41 to R45 are the same as or different from each other, and can each independently be hydrogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

[0206] In another embodiment, R41 to R45 are the same as or different from each other, and each can independently be hydrogen; substituted or unsubstituted C1-C40 alkyl; substituted or unsubstituted C6-C40 aryl; or substituted or unsubstituted C2-C40 heteroaryl.

[0207] In another embodiment, R41 to R45 are the same as or different from each other, and each can independently be hydrogen; C6-C40 aryl unsubstituted or substituted with one or more substituents selected from C1-C20 alkyl, C6-C40 aryl, C2-C40 heteroaryl, -P(=)ORR', and -SiRR'R''; or C2-C40 heteroaryl.

[0208] In another embodiment, R41 to R45 are the same as or different from each other, and each can independently be hydrogen; phenyl unsubstituted or substituted with one or more substituents selected from phenyl, triphenylene, diphenylfluorenyl, -P(=)ORR', and -SiRR'R''; biphenyl; dibenzofuranyl; dibenzothiophenyl; or dimethylfluorenyl.

[0209] In one embodiment of the present application, R, R', and R'' are the same as or different from each other, and each can independently be substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

[0210] In another embodiment, R, R', and R'' are the same as or different from each other, and each can independently be substituted or unsubstituted C6-C60 aryl.

[0211] In another embodiment, R, R', and R'' are the same as or different from each other, and each can independently be substituted or unsubstituted C6-C60 monocyclic or polycyclic aryl.

[0212] In another embodiment, R, R', and R'' are the same as or different from each other, and each can independently be substituted or unsubstituted C6-C40 monocyclic aryl.

[0213] In another embodiment, R, R', and R'' are the same as or different from each other, and each can independently be C6-C20 monocyclic aryl.

[0214] In another embodiment, R, R', and R'' can be phenyl.

[0215] In one embodiment of the present application, Chemical Formula 2 can be represented by any one of Chemical Formulas 2-1 to 2-6 below.

[0216] [Chemical Formula 2-1]

[0217]

[0218] [Chemical Formula 2-2]

[0219]

[0220] [Chemical Formula 2-3]

[0221]

[0222] [Chemical Formula 2-4]

[0223]

[0224] [Chemical Formula 2-5]

[0225]

[0226] [Chemical Formula 2-6]

[0227]

[0228] In Chemical Formulas 2-1 to 2-6,

[0229] R11 to R19, A1, A2 and d have the same definitions as in Chemical Formula 2.

[0230] In one embodiment of the present application, A1 and A2 are the same as or different from each other, and each independently is O; S; NRa; or CRbRc.

[0231] In one embodiment of the present application, A1 is O; S; NRa; or CRbRc.

[0232] In one embodiment of the present application, A2 is O; S; NRa; or CRbRc.

[0233] In one embodiment of the present application, A1 is S.

[0234] In one embodiment of the present application, A2 is S.

[0235] In one embodiment of the present application, A1 is O.

[0236] In one embodiment of the present application, A2 is O.

[0237] In one embodiment of the present application, A1 is NRa.

[0238] In one embodiment of the present application, A2 is NRa.

[0239] In one embodiment of the present application, A1 is CRbRc.

[0240] In one embodiment of the present application, A2 is CRbRc.

[0241] In one embodiment of the present application, Ra may be a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group.

[0242] In one embodiment of the present application, Ra may be a substituted or unsubstituted C6 - C40 aryl group; or a substituted or unsubstituted C2 - C40 heteroaryl group.

[0243] In another embodiment, Ra may be a C6 - C40 aryl group that is unsubstituted or substituted with one or more substituents selected from C1 - C10 alkyl groups, C6 - C20 aryl groups, and SiRR'R''; or a C2 - C40 heteroaryl group that is unsubstituted or substituted with a C6 - C10 aryl group.

[0244] In another embodiment, Ra may be a C6 - C20 aryl group that is unsubstituted or substituted with one or more substituents selected from C1 - C10 alkyl groups, C6 - C20 aryl groups, and SiRR'R''; or a C2 - C20 heteroaryl group that is unsubstituted or substituted with a C6 - C10 aryl group.

[0245] In another embodiment, Ra may be a phenyl group that is unsubstituted or substituted with one or more substituents selected from phenyl, biphenyl, and triphenylsilyl; biphenyl; naphthyl; terphenyl; triphenylene; dimethylfluorenyl; diphenylfluorenyl; dibenzofuranyl; dibenzothiophenyl; or a carbazolyl group that is unsubstituted or substituted with a phenyl group.

[0246] In one embodiment of the present application, Rb and Rc are the same as or different from each other, and may each independently be a substituted or unsubstituted C1 - C60 alkyl group.

[0247] In another embodiment, Rb and Rc are the same as or different from each other, and may each independently be a substituted or unsubstituted C1 - C40 alkyl group.

[0248] In another embodiment, Rb and Rc are the same as or different from each other, and may each independently be a substituted or unsubstituted C1 - C20 alkyl group.

[0249] In another embodiment, Rb and Rc are the same as or different from each other, and may each independently be a C1 - C20 alkyl group.

[0250] In another embodiment, Rb and Rc are the same as or different from each other, and may each independently be a C1 - C20 linear alkyl group.

[0251] In another embodiment, Rb and Rc are the same as or different from each other and can each independently be a C1 to C10 linear alkyl group.

[0252] In another embodiment, Rb and Rc are the same as or different from each other and can each independently be a C1 to C5 linear alkyl group.

[0253] In another embodiment, Rb and Rc can be methyl.

[0254] In one embodiment of the present application, R11 and R14 to R19 can be hydrogen.

[0255] In one embodiment of the present application, Chemical Formula 2 can be represented by any one of Chemical Formulas 2-7 to 2-9 below.

[0256] [Chemical Formula 2-7]

[0257]

[0258] [Chemical Formula 2-8]

[0259]

[0260] [Chemical Formula 2-9]

[0261]

[0262] In Chemical Formulas 2-7 to 2-9,

[0263] A1, A2, R11 and R14 have the same definitions as in Chemical Formula 2,

[0264] A3 is O; S; or NRg,

[0265] R50 and R51 are hydrogen; or a substituted or unsubstituted C6 to C60 aryl group, and at least one of them is a substituted or unsubstituted C6 to C60 aryl group,

[0266] Rg, R52 and R53 are the same as or different from each other and each independently is hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0267] r is an integer from 0 to 3, and

[0268] q is an integer from 0 to 4.

[0269] In one embodiment of the present application, R50 and R51 can be hydrogen; or a substituted or unsubstituted C6 to C60 aryl group.

[0270] In another embodiment, R50 and R51 can be hydrogen; or a substituted or unsubstituted C6 to C40 aryl group.

[0271] In another embodiment, R50 and R51 can be hydrogen; or a C6 to C40 aryl group.

[0272] In another embodiment, R50 and R51 can be hydrogen; phenyl; or triphenylene.

[0273] In one embodiment of the present application, at least one of R50 and R51 can be a substituted or unsubstituted C6 to C60 aryl group.

[0274] In one embodiment of the present application, R52 and R53 can be hydrogen.

[0275] In one embodiment of the present application, Rg can be a substituted or unsubstituted C6 to C60 aryl group.

[0276] In another embodiment, Rg can be a substituted or unsubstituted C6 to C40 aryl group.

[0277] In another embodiment, Rg can be a C6 to C40 aryl group.

[0278] In another embodiment, Rg can be phenyl; or biphenyl.

[0279] When having a fused-type basic ring as in Chemical Formula 2-7, when used together with the heterocyclic compound of Chemical Formula 1 in an organic light-emitting device, very fast hole transport characteristics are particularly obtained as a host material, which reduces the threshold voltage and driving voltage of the device, thereby allowing the device to be driven even at a low voltage.

[0280] When having a substituent (R50) in the fused-type ring structure as in Chemical Formula 2-8, a larger structure is obtained compared to Chemical Formula 2-7, and due to this property, as the conjugated region extending from the basic skeleton to the substituent (R50) becomes wider, the region at the HOMO energy level is more enlarged. Therefore, holes are distributed to a wide HOMO energy level region, and the hole transport ability can be maintained more stably. In other words, in the case of Chemical Formula 2-8, although the driving voltage increases to a certain extent, the overall lifetime characteristics are more excellent.

[0281] In Chemical Formula 2-9, the fused ring structure is substituted with a heteroaryl group, and in addition to the characteristic of maintaining a stable HOMO energy level through a wide conjugation region as in Chemical Formula 2-8, substitution with several heteroaryl groups allows for use as an auxiliary means for controlling the bandgap. In particular, although the driving voltage is slightly increased due to having the largest structure compared to the basic skeleton, dibenzofuranyl / dibenzothiophenyl, etc. have the highest structural stability and maintain a higher T1 level, and thus the device has particularly excellent lifetime characteristics.

[0282] When the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are simultaneously included in the organic material layer of the organic light-emitting device, the effects of more excellent efficiency and lifetime are obtained. Such a result can lead to the prediction that an exciplex phenomenon occurs when the two compounds are simultaneously included.

[0283] The exciplex phenomenon is a phenomenon in which energy of the magnitude of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is released due to electron exchange between two molecules. When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, and thus the internal quantum efficiency of fluorescence can increase up to 100%. When a donor (p-host) having good hole transport ability and an acceptor (n-host) having good electron transport ability are used as the host of the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, and thus the driving voltage can be reduced, which contributes to an improvement in lifetime.

[0284] According to one embodiment of the present application, Chemical Formula 1 can be represented by any one of the following compounds, but is not limited thereto.

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299]

[0300]

[0301]

[0302]

[0303]

[0304]

[0305] In one embodiment of the present application, Formula 2 can be represented by any one of the following compounds, but is not limited thereto.

[0306]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313]

[0314] In addition, by introducing various substituents into the structures of Formulas 1 and 2, compounds with unique properties of the introduced substituents can be synthesized. For example, by introducing substituents that are commonly used as hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials for manufacturing organic light-emitting devices into the core structure, materials that meet the requirements of each organic material layer can be synthesized.

[0315] In addition, by introducing various substituents into the structures of Chemical Formulas 1 and 2, the bandgap can be finely controlled, and at the same time, the characteristics at the interface between organic materials can be enhanced, and material applications can become diversified.

[0316] At the same time, the heterocyclic compound represented by Chemical Formula 2 has a high glass transition temperature (Tg) and excellent thermal stability. Such an improvement in thermal stability becomes an important factor in providing driving stability to the device.

[0317] The heterocyclic compound according to an embodiment of the present application can be prepared using a multi-step chemical reaction. First, some intermediate compounds are prepared, and the heterocyclic compound of Chemical Formula 1 or 2 can be prepared from these intermediate compounds. More specifically, the heterocyclic compound according to an embodiment of the present application can be prepared based on the preparation examples described later.

[0318] In addition, another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, the composition containing a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0319] The specific descriptions of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are the same as those provided above.

[0320] In the composition, the weight ratio of the heterocyclic compound represented by Chemical Formula 1: the heterocyclic compound represented by Chemical Formula 2 can be 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1. However, the weight ratio is not limited thereto.

[0321] The composition can be used when forming the organic material of the organic light-emitting device, and can be more preferably used when forming the host of the light-emitting layer.

[0322] The composition has a form in which two or more compounds are simply mixed, and the material in powder state can be mixed before forming the organic material layer of the organic light-emitting device, or the compound in liquid state can be mixed at an appropriate temperature or higher. The composition is in a solid state below the melting point of each material and can be maintained in a liquid state when adjusting the temperature.

[0323] The composition can also contain materials known in the art, such as solvents and additives.

[0324] The organic light-emitting device according to an embodiment of the present application can be manufactured using common organic light-emitting device manufacturing methods and materials, except that the above-mentioned heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are used to form one or more organic material layers.

[0325] When manufacturing an organic light-emitting device, a compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2 can be formed into an organic material layer using a solution coating method and a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0326] The organic material layer of the organic light-emitting device of the present disclosure can be formed into a single-layer structure, or can also be formed into a multi-layer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of the present disclosure can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and can include a smaller number of organic material layers.

[0327] Specifically, an organic light-emitting device according to an embodiment of the present application includes: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0328] In one embodiment of the present application, the first electrode can be an anode, and the second electrode can be a cathode.

[0329] In another embodiment, the first electrode can be a cathode, and the second electrode can be an anode.

[0330] In one embodiment of the present application, the organic light-emitting device can be a blue organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 and the heterocyclic compound according to Chemical Formula 2 can be used as materials for the blue organic light-emitting device.

[0331] In one embodiment of the present application, the organic light-emitting device can be a green organic light-emitting device, and the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 can be used as materials for the green organic light-emitting device.

[0332] In one embodiment of the present application, the organic light-emitting device can be a red organic light-emitting device, and the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 can be used as materials for the red organic light-emitting device.

[0333] The organic light-emitting device of the present disclosure can also include one, two 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.

[0334] In the organic light-emitting device provided in one embodiment of the present application, the organic material layer includes at least one of a hole-blocking layer, an electron-injection layer, and an electron-transport layer, and at least one of the hole-blocking layer, the electron-injection layer, and the electron-transport layer simultaneously contains a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0335] In one embodiment of the present application, the organic material layer includes a light-emitting layer, and the light-emitting layer contains a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0336] In one embodiment of the present application, the organic material layer includes a light-emitting layer, the light-emitting layer contains a host material, and the host material contains a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0337] Figures 1 to 3 The lamination order of the electrodes and the organic material layer of an organic light-emitting device according to one embodiment of the present application is shown. However, the scope of the present application is not limited to these figures, and the structures of organic light-emitting devices known in the art can also be used in the present application.

[0338] Figure 1 An organic light-emitting device is shown in which an anode (200), an organic material layer (300), and a cathode (400) are sequentially laminated on a substrate (100). However, the structure is not limited to such a structure, and as Figure 2 shown, an organic light-emitting device in which a cathode, an organic material layer, and an anode are sequentially laminated on a substrate can also be obtained.

[0339] Figure 3 The case where the organic material layer is multilayer is shown. According to Figure 3 the 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 such a lamination structure, and according to needs, layers other than the light-emitting layer may not be included, and other necessary functional layers may also be added.

[0340] One embodiment of the present application provides a method for manufacturing an organic light-emitting device, the method including: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein the formation of the organic material layer includes using a composition for an organic material layer according to one embodiment of the present application to form one or more organic material layers.

[0341] In a method for manufacturing an organic light emitting device provided in an embodiment of the present application, the formation of the organic material layer is performed using a thermal vacuum deposition method after premixing a heterocyclic compound of Chemical Formula 1 and a heterocyclic compound of Chemical Formula 2.

[0342] Premixing means first mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 in one supply source before depositing on the organic material layer. Premixing uses one supply source instead of two or three supply sources and has the advantage of simplifying the process.

[0343] The premixed material can be referred to as a composition for an organic material layer according to an embodiment of the present application.

[0344] When premixing is performed as described above, it is necessary to check the unique thermal properties of each material before mixing. Here, depending on the unique thermal properties of the materials, depositing the premixed host material from one supply source may greatly affect the deposition conditions (including the deposition rate). When the thermal properties between two or more types of materials to be premixed are not similar and are very different, it may not be possible to maintain repeatability and reproducibility during the deposition process, which means that it may not be possible to fabricate all uniform OLEDs in one deposition process.

[0345] To overcome this problem, the electrical properties of the materials can be adjusted by using an appropriate combination of the basic structure and substituents of each material, and in addition, the thermal properties of the materials can be controlled according to the molecular structure form. Therefore, by using various substituents other than the basic skeleton in Chemical Formula 2 and using the C-N bonding of fused carbazole as in Chemical Formula 2, it is possible to ensure diversification of various premixed deposition processes between hosts by controlling the thermal properties of each material and attempting to improve device performance. This has the advantage of ensuring diversification of premixed deposition processes using three, four or more host materials and two compounds as hosts.

[0346] In an organic light emitting device according to an embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 are shown below. However, these are for illustrative purposes only and are not intended to limit the scope of the present application, and can be replaced by materials known in the art.

[0347] As the anode material, a material having a relatively large work function can be used, and transparent conductive oxides, metals, conductive polymers, etc. can be used. Specific examples of the anode 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 SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylenedioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but not limited thereto.

[0348] As the cathode material, a material having a relatively small work function can be used, and metals, metal oxides, conductive polymers, etc. can be used. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and so on, but not limited thereto.

[0349] As the hole injection material, known hole injection materials can be used. For example, phthalocyanine compounds can be used, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or starburst amine derivatives described in the literature [Advanced Material, 6, page 677 (1994)], such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB); polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrene-sulfonate) as conductive polymers having solubility; and so on.

[0350] As the hole transport material, pyrazoline derivatives, arylamine-based derivatives, derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight materials or high molecular weight materials can also be used.

[0351] As the electron transport material, metal complexes of oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, biphenylenequinone derivatives, 8-hydroxyquinoline and its derivatives, etc. can be used, and high molecular weight materials and low molecular weight materials can also be used.

[0352] As an example of an electron injection material, LiF is commonly used in the art. However, the present application is not limited thereto.

[0353] As the light-emitting material, a red light-emitting material, a green light-emitting material, or a blue light-emitting material can be used, and if necessary, two or more light-emitting materials can be mixed and used. Herein, two or more light-emitting materials can be used by depositing them as separate supply sources or by pre-mixing and depositing them as one supply source. In addition, a fluorescent material can also be used as the light-emitting material. However, a phosphorescent material can also be used. As the light-emitting material, a material that emits light by combining electrons and holes injected from the anode and the cathode, respectively, can be used alone. However, a material having a host material and a dopant material that participate in light emission together can also be used.

[0354] When mixing the light-emitting material host, hosts of the same series can be mixed, or hosts of different series can be mixed. For example, any two or more types of materials selected from n-type host materials or p-type host materials can be used as the host material of the light-emitting layer.

[0355] Depending on the materials used, the organic light-emitting device according to an embodiment of the present application can be a top-emission type, a bottom-emission type, or a dual-emission type.

[0356] Under a similar principle for use in an organic light-emitting device, the heterocyclic compound according to an embodiment of the present application can also be used in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.

[0357] Embodiments of the Invention

[0358] Hereinafter, the present specification will be described in more detail with reference to examples. However, these examples are for illustrative purposes only, and the scope of the present application is not limited thereto.

[0359] <Preparation Example>

[0360] <Preparation Example 1> Preparation of Compound 1-1

[0361]

[0362] 1) Preparation of Compound 1-1-6

[0363] Dissolve 4-bromo-2-fluoro-1-iodobenzene (200.0 g, 664.7 mM), (2-chloro-6-methoxyphenyl)boronic acid (148.7 g, 794.6 mM), Pd(PPh)4 (38.4 g, 33.2 mM), and K2CO3 (183.7 g, 1329.4 mM) in 1,4-di In alkane / H2O (1 L / 200 mL), and reflux for 24 hours. After the reaction is completed, the product is extracted by introducing distilled water and dichloromethane (DCM) into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction material is purified by column chromatography (DCM:Hex = 1:3) to obtain the target compound 1-1-6 (178 g, 85%).

[0364] 2) Preparation of Compound 1-1-5

[0365] Dissolve Compound 1-1-6 (178 g, 564.1 mM) and BBr3 (107 mL, 1128.2 mM) in DCM (800 mL), and reflux for 1 hour. After the reaction is completed, the product is extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction material is purified by column chromatography (DCM:Hex = 1:1) to obtain the target compound 1-1-5 (153.1 g, 90%).

[0366] 3) Preparation of Compound 1-1-4

[0367] Dissolve Compound 1-1-5 (153 g, 507.4 mM) and K2CO3 (140.3 g, 1014.8 mM) in dimethylformamide (DMF) (800 mL), and reflux for 4 hours. After the reaction is completed, the product is extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction material is purified by column chromatography (DCM:Hex = 1:9) and recrystallized from methanol to obtain the target compound 1-1-4 (88.5 g, 62%).

[0368] 4) Preparation of Compound 1-1-3

[0369] Dissolve Compound 1-1-4 (88.5 g, 314.4 mM), bis(pinacolato)diboron (159.7 g, 628.8 mM), PdCl2(dppf) (23.0 g, 31.4 mM), and KOAc (92.6 g, 943.2 mM) in 1,4-di alkane (500 mL), and reflux for 24 hours. After the reaction is completed, the product is extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction material is purified by column chromatography (DCM:Hex = 1:5) to obtain the target compound 1-1-3 (85.7 g, 83%).

[0370] 5) Preparation of Compound 1-1-2

[0371] Dissolve Compound 1-1-3 (85.0 g, 258.7 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (69.3 g, 258.7 mM), Pd(PPh)4 (14.9 g, 12.9 mM) and K2CO3 (71.5 g, 517.4 mM) in 1,4-d ane / H2O (1000 mL / 200 mL), and reflux for 24 hours. After the reaction is completed, extract the resulting product by introducing distilled water and DCM to the resulting product at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the reaction material by column chromatography (DCM:Hex = 1:4), and recrystallize with methanol to obtain the target compound 1-1-2 (79.7 g, 71%).

[0372] 6) Preparation of Compound 1-1-1

[0373] Dissolve Compound 1-1-2 (79.0 g, 182.1 mM), bis(pinacolato)diboron (92.5 g, 364.2 mM), Pd(dba)2 (10.5 g, 18.2 mM), XPhos (17.4 g, 36.4 mM) and KOAc (53.6 g, 546.3 mM) in 1,4-d ane (800 mL), and reflux for 24 hours. After the reaction is completed, extract the resulting product by introducing distilled water and DCM to the resulting product at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the reaction material by column chromatography (DCM:Hex = 1:5) to obtain the target compound 1-1-1 (84.2 g, 88%).

[0374] 7) Preparation of Compound 1-1

[0375] Dissolve Compound 1-1-1 (15.0 g, 28.5 mM), 2-bromodibenzo[b,d]furan (7.8 g, 31.4 mM), Pd(PPh)4 (1.6 g, 1.4 mM) and K2CO3 (7.9 g, 57.0 mM) in 1,4-d ane / H2O (200 mL / 40 mL), and reflux for 24 hours. After the reaction is completed, extract the resulting product by introducing distilled water and DCM to the resulting product at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Purify the reaction material by column chromatography (DCM:Hex = 1:3), and recrystallize with methanol to obtain the target compound 1-1 (13.2 g, 82%).

[0376] The target compound A was synthesized in the same manner as in Preparation Example 1, except that Intermediate A in Table 1 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate B in Table 1 below was used instead of 2-bromodibenzo[b,d]furan.

[0377] [Table 1]

[0378]

[0379]

[0380] <Preparation Example 2> Preparation of Compound 2-1

[0381]

[0382] 1) Preparation of Compound 2-1-6

[0383] 4-Bromo-2-fluoro-1-iodobenzene (200.0 g, 664.7 mM), (5-chloro-2-methoxyphenyl)boronic acid (148.7 g, 794.6 mM), Pd(PPh)4 (38.4 g, 33.2 mM) and K2CO3 (183.7 g, 1329.4 mM) were dissolved in 1,4-di ane / H2O (1 L / 200 mL) and refluxed for 24 hours. After completion of the reaction, the resulting product was extracted by introducing distilled water and DCM to the resulting product at room temperature, and after drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:4) to obtain the target compound 2-1-6 (174 g, 83%).

[0384] 2) Preparation of Compound 2-1-5

[0385] Compound 2-1-6 (174 g, 551.4 mM) and BBr3 (105 mL, 1102.8 mM) were dissolved in DCM (800 mL) and refluxed for 1 hour. After completion of the reaction, the resulting product was extracted by introducing distilled water and DCM to the resulting product at room temperature, and after drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) to obtain the target compound 2-1-5 (148.0 g, 89%).

[0386] 3) Preparation of Compound 2-1-4

[0387] Compound 2-1-5 (148 g, 491.3 mM) and K2CO3 (135.8 g, 982.8 mM) were dissolved in DMF (800 mL) and refluxed for 4 hours. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM to the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction substance was purified by column chromatography (DCM:Hex = 1:8) and recrystallized from methanol to obtain the target compound 2-1-4 (78.8 g, 57%).

[0388] 4) Preparation of Compound 2-1-3

[0389] Compound 2-1-4 (78.0 g, 277.1 mM), bis(pinacolato)diboron (140.7 g, 554.2 mM), PdCl2(dppf) (20.3 g, 27.7 mM) and KOAc (81.6 g, 831.3 mM) were dissolved in 1,4-di ane (500 mL) and refluxed for 24 hours. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM to the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction substance was purified by column chromatography (DCM:Hex = 1:5) to obtain the target compound 2-1-3 (77.4 g, 85%).

[0390] 5) Preparation of Compound 2-1-2

[0391] Compound 2-1-3 (77.0 g, 234.3 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (67.7 g, 234.3 mM), Pd(PPh)4 (13.5 g, 11.7 mM) and K2CO3 (64.8 g, 468.6 mM) were dissolved in 1,4-di ane / H2O (1000 mL / 200 mL) and refluxed for 24 hours. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM to the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction substance was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain the target compound 2-1-2 (74.2 g, 73%).

[0392] 6) Preparation of Compound 2-1-1

[0393] Compound 2-1-2 (74.0 g, 170.6 mM), bis(pinacolato)diboron (86.6 g, 341.2 mM), Pd(dba)2 (9.8 g, 17.1 mM), XPhos (16.3 g, 34.1 mM) and KOAc (50.2 g, 511.8 mM) were dissolved in 1,4-dibutane (800 mL) and refluxed for 24 hours. After completion of the reaction, the resulting product was extracted by introducing distilled water and dichloromethane (DCM) to the resulting product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:4) to obtain the target compound 2-1-1 (78.0 g, 87%). After completion of the reaction, the resulting product was extracted by introducing distilled water and dichloromethane (DCM) to the resulting product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:4) to obtain the target compound 2-1-1 (78.0 g, 87%).

[0394] 7) Preparation of Compound 2-1

[0395] Compound 2-1-1 (15.0 g, 28.5 mM), 2-bromodibenzofuran (7.8 g, 31.4 mM), Pd(PPh)4 (1.6 g, 1.4 mM) and K2CO3 (7.9 g, 57.0 mM) were dissolved in 1,4-dibutane / H2O (200 mL / 40 mL) and refluxed for 24 hours. After completion of the reaction, the resulting product was extracted by introducing distilled water and dichloromethane (DCM) to the resulting product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain the target compound 2-1 (13.7 g, 85%). After completion of the reaction, the resulting product was extracted by introducing distilled water and dichloromethane (DCM) to the resulting product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain the target compound 2-1 (13.7 g, 85%).

[0396] The target compound A was synthesized in the same manner as in Preparation Example 2, except that Intermediate A in Table 2 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate B in Table 2 below was used instead of 2-bromodibenzofuran.

[0397] [Table 2]

[0398]

[0399]

[0400] [Preparation Example 3] Preparation of Compound 3-1

[0401]

[0402] 1) Preparation of Compound 3-1-6

[0403] 4-Bromo-2-fluoro-1-iodobenzene (200.0 g, 664.7 mM), (4-chloro-2-methoxyphenyl)boronic acid (148.7 g, 794.6 mM), Pd(PPh)4 (38.4 g, 33.2 mM), and K2CO3 (183.7 g, 1329.4 mM) were dissolved in 1,4-di ane / H2O (1 L / 200 mL) and refluxed for 24 h. After the reaction was complete, the resulting mixture was extracted by introducing distilled water and dichloromethane (DCM) thereto at room temperature, and after drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:3) to obtain the target compound 3-1-6 (170 g, 81%).

[0404] 2) Preparation of Compound 3-1-5

[0405] Compound 3-1-6 (170 g, 538.7 mM) and BBr3 (102 mL, 1078 mM) were dissolved in DCM (800 mL) and refluxed for 1 h. After the reaction was complete, the resulting mixture was extracted by introducing distilled water and DCM thereto at room temperature, and after drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:1) to obtain the target compound 3-1-5 (148 g, 91%).

[0406] 3) Preparation of Compound 3-1-4

[0407] Compound 3-1-5 (148 g, 490.8 mM) and K2CO3 (135.6 g, 981.6 mM) were dissolved in DMF (800 mL) and refluxed for 4 h. After the reaction was complete, the resulting mixture was extracted by introducing distilled water and DCM thereto at room temperature, and after drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:9) and recrystallized from methanol to obtain the target compound 3-1-4 (84.1 g, 61%).

[0408] 4) Preparation of Compound 3-1-3

[0409] Compound 3-1-4 (84.1 g, 298.8 mM), bis(pinacolato)diboron (151.6 g, 597.5 mM), PdCl2(dppf) (21.9 g, 29.9 mM), and KOAc (88.0 g, 896.4 mM) were dissolved in 1,4-di In alkane (500 mL), and reflux for 24 hours. After the reaction is completed, the resulting product is extracted by introducing distilled water and DCM to the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction substance is purified by column chromatography (DCM:Hex = 1:5) to obtain the target compound 3-1-3 (82.6 g, 84%).

[0410] 5) Preparation of compound 3-1-2

[0411] Dissolve compound 3-1-3 (82.6 g, 251.4 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (67.3 g, 251.4 mM), Pd(PPh)4 (14.6 g, 12.6 mM) and K2CO3 (69.49 g, 502.8 mM) in 1,4-di alkane / H2O (1000 mL / 200 mL), and reflux for 24 hours. After the reaction is completed, the resulting product is extracted by introducing distilled water and DCM to the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction substance is purified by column chromatography (DCM:Hex = 1:4) and recrystallized from methanol to obtain the target compound 3-1-2 (79.7 g, 71%).

[0412] 6) Preparation of compound 3-1-1

[0413] Dissolve compound 3-1-2 (76.3 g, 175.9 mM), bis(pinacolato)diboron (92.5 g, 351.7 mM), Pd(dba)2 (10.1 g, 17.6 mM), XPhos (16.8 g, 35.2 mM) and KOAc (51.8 g, 527.6 mM) in 1,4-di alkane (800 mL), and reflux for 24 hours. After the reaction is completed, the resulting product is extracted by introducing distilled water and DCM to the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction substance is purified by column chromatography (DCM:Hex = 1:5) to obtain the target compound 3-1-1 (79.5 g, 83%).

[0414] 7) Preparation of compound 3-1

[0415] Dissolve compound 3-1-1 (15.0 g, 28.5 mM), 2-bromodibenz[b,d]furan (7.8 g, 31.4 mM), Pd(PPh)4 (1.6 g, 1.4 mM) and K2CO3 (7.9 g, 57.0 mM) in 1,4-di In alkane / H2O (200 mL / 40 mL), and reflux for 24 hours. After the reaction is completed, the obtained product is extracted by introducing distilled water and DCM into the obtained product at room temperature, and after drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction substance is purified by column chromatography (DCM:Hex = 1:3) and recrystallized with methanol to obtain the target compound 3-1 (13.6 g, 85%).

[0416] The target compound A was synthesized in the same manner as in Preparation Example 3, except that Intermediate A in Table 3 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate B in Table 3 below was used instead of 2-bromodibenzo[b,d]furan.

[0417] [Table 3]

[0418]

[0419]

[0420] [Preparation Example 4] Preparation of Compound 4-1

[0421]

[0422] 1) Preparation of Compound 4-1-6

[0423] Dissolve 4-bromo-2-fluoro-1-iodobenzene (200.0 g, 664.7 mM), (3-chloro-2-methoxyphenyl)boronic acid (148.7 g, 794.6 mM), Pd(PPh)4 (38.4 g, 33.2 mM) and K2CO3 (183.7 g, 1329.4 mM) in 1,4-di alkane / H2O (1 L / 200 mL), and reflux for 24 hours. After the reaction is completed, the obtained product is extracted by introducing distilled water and DCM into the obtained product at room temperature, and after drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. The reaction substance is purified by column chromatography (DCM:Hex = 1:4) to obtain the target compound 4-1-6 (169 g, 81%).

[0424] 2) Preparation of Compound 4-1-5

[0425] Compound 4-1-6 (169 g, 535.5 mM) and BBr3 (103 mL, 1071.0 mM) were dissolved in dichloromethane (DCM) (800 mL) and refluxed for 1 hour. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) to obtain the target compound 4-1-5 (145.3 g, 90%).

[0426] 3) Preparation of Compound 4-1-4

[0427] Compound 4-1-5 (145.3 g, 481.9 mM) and K2CO3 (133.2 g, 963.9 mM) were dissolved in DMF (800 mL) and refluxed for 4 hours. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:8) and recrystallized from methanol to obtain the target compound 4-1-4 (74.6 g, 57%).

[0428] 4) Preparation of Compound 4-1-3

[0429] Compound 4-1-4 (74.6 g, 265.1 mM), bis(pinacolato)diboron (134.6 g, 530.2 mM), PdCl2(dppf) (19.4 g, 26.5 mM) and KOAc (78.1 g, 795.3 mM) were dissolved in 1,4-di ane (500 mL) and refluxed for 24 hours. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) to obtain the target compound 4-1-3 (76.7 g, 88%).

[0430] 5) Preparation of Compound 4-1-2

[0431] Compound 4-1-3 (76.7 g, 233.28 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (67.7 g, 233.28 mM), Pd(PPh)4 (13.5 g, 11.7 mM) and K2CO3 (64.5 g, 466.6 mM) were dissolved in 1,4-di in alkane / H2O (800 mL / 160 mL), and refluxed for 24 hours. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction substance was purified by column chromatography (DCM:Hex = 1:5), and recrystallized from methanol to obtain the target compound 4-1-2 (70.9 g, 70%).

[0432] 6) Preparation of Compound 4-1-1

[0433] Compound 4-1-2 (74.0 g, 163.3 mM), bis(pinacolato)diboron (g, 326.6 mM), Pd(dba)2 (9.4 g, 16.3 mM), XPhos (15.6 g, 32.7 mM) and KOAc (48.1 g, 489.9 mM) were dissolved in 1,4-di alkane (740 mL), and refluxed for 24 hours. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction substance was purified by column chromatography (DCM:Hex = 1:4) to obtain the target compound 4-1-1 (72.9 g, 85%).

[0434] 7) Preparation of Compound 4-1

[0435] Compound 4-1-1 (15.0 g, 28.5 mM), 2-bromodibenzofuran (7.8 g, 31.4 mM), Pd(PPh)4 (1.6 g, 1.4 mM) and K2CO3 (7.9 g, 57.0 mM) were dissolved in 1,4-di alkane / H2O (200 mL / 40 mL), and refluxed for 24 hours. After the reaction was completed, the resulting product was extracted by introducing distilled water and DCM into the obtained product at room temperature. After drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction substance was purified by column chromatography (DCM:Hex = 1:3), and recrystallized from methanol to obtain the target compound 4-1 (12.9 g, 80%).

[0436] The target compound A was synthesized in the same manner as in Preparation Example 4, except that Intermediate A in Table 4 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, and Intermediate B in Table 4 below was used instead of 2-bromodibenzofuran.

[0437] [Table 4]

[0438]

[0439]

[0440] <Preparation Example 5> Synthesis of Compound 5-6

[0441]

[0442] 1) Preparation of Compound 5-6

[0443] Dissolve 5-phenyl-5,7-dihydroindolo[2,3-b]carbazole (6.0 g, 18.05 mM), 4-bromo-1,1';4',1''-terphenyl (6.7 g, 21.66 mM), Pd2(dba)3 (0.824 g, 0.90 mM), Sphos (0.74 g, 1.80 mM) and t-BuONa (3.47 g, 36.10 mM) in 1,4- alkane (60 mL) and reflux for 24 hours. After the reaction is completed, extract the resulting product by introducing distilled water and DCM into the obtained product at room temperature, and after drying the organic layer with MgSO4, remove the solvent using a rotary evaporator. Dissolve the reaction substance in DCB (100 ml) and purify it by filtration through silica gel, and recrystallize with methanol to obtain the target compound 5-6 (8.6 g, 85%).

[0444] Synthesize the target compound A in the same manner as in Preparation Example 5, except that intermediate A in Table 5 below is used instead of 4-bromo-1,1';4',1''-terphenyl, and intermediate B in Table 5 below is used instead of 5-phenyl-5,7-dihydroindolo[2,3-b]carbazole.

[0445] [Table 5]

[0446]

[0447] <Preparation Example 6> Synthesis of Compound 5-79

[0448]

[0449] 6-1) Preparation of Compound 5-79-2

[0450] Dissolve 2-chloro-7-phenyl-5,7-dihydroindolo[2,3-b]carbazole (7.0 g, 19.08 mM), iodobenzene (4.28 g, 20.99 mM), Pd2(dba)3 (0.873 g, 0.95 mM), (t-Bu)3P (0.58 g, 2.86 mM) and t-BuONa (3.67 g, 38.16 mM) in toluene (70 mL) and reflux for 4 hours. After completion of the reaction, the resulting product is extracted by introducing distilled water and DCM to the obtained product at room temperature, and after drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator.

[0451] Purify the reaction material using an MC / HEX column and remove the solvent using a rotary evaporator to obtain the target compound 5-79-2 (6.93 g, 82%).

[0452] Synthesize the target compound C-2 in the same manner as in Preparation Example 6-1, except that the intermediate C-3 in Table 6 below is used instead of 2-chloro-7-phenyl-5,7-dihydroindolo[2,3-b]carbazole.

[0453] [Table 6]

[0454]

[0455] 6-2) Preparation of Compound 5-79-1

[0456]

[0457] Dissolve 2-chloro-5,7-diphenyl-5,7-dihydroindolo[2,3-b]carbazole (6.93 g, 15.65 mM), bis(pinacolato)diboron (5.96 g, 23.47 mM), Pd2(dba)3 (1.43 g, 1.56 mM), XPhos (1.49 g, 3.13 mM) and KOAc (4.61 g, 46.94 mM) in 1,4- alkane (70 mL) and reflux for 5 hours. After completion of the reaction, the resulting product is extracted by introducing distilled water and DCM to the obtained product at room temperature, and after drying the organic layer with MgSO4, the solvent is removed using a rotary evaporator. Purify the reaction material using an MC / HEX column and concentrate the filtrate under vacuum to obtain the target compound 5-79-1 (6.8 g, 81%).

[0458] Synthesize the target compound C-1 in the same manner as in Preparation Example 6-2, except that the intermediate C-2 in Table 7 below is used instead of 2-chloro-5,7-diphenyl-5,7-dihydroindolo[2,3-b]carbazole.

[0459] [Table 7]

[0460]

[0461] 6-3) Preparation of Compound 5-79

[0462]

[0463] 5,7-Diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,7-dihydroindolo[2,3-b]carbazole (6.8 g, 12.72 mM), 3-bromo-9-phenylcarbazole (4.51 g, 14.00 mM), Pd(PPh3)4 (0.74 g, 0.64 mM) and K2CO3 (3.52 g, 25.45 mM) were dissolved in toluene (70 mL) / ethanol (15 mL) / water (15 mL) and refluxed for 4 hours. After completion of the reaction, the resulting product was extracted by introducing distilled water and DCM into the obtained product at room temperature, and after drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction substance was purified using an MC / HEX column and the filtrate was concentrated under vacuum to obtain the target compound 5-79 (6.61 g, 80%).

[0464] The target compound C was synthesized in the same manner as in Preparation Example 6-3, except that intermediate C-1 in Table 8 below was used instead of 5,7-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,7-dihydroindolo[2,3-b]carbazole, and intermediate D-1 in Table 8 below was used instead of 3-bromo-9-phenylcarbazole.

[0465] [Table 8]

[0466]

[0467] Compounds of Formula 1 and compounds of Formula 2 other than the compounds prepared in the preparation examples were also prepared in the same manner. The synthesis confirmation data of the compounds prepared above are as described in the following [Table 9] and [Table 10].

[0468] [Table 9]

[0469]

[0470]

[0471]

[0472]

[0473] [Table 10]

[0474]

[0475]

[0476] <Experimental Example 1> Fabrication of Organic Light-Emitting Device

[0477] A glass substrate coated with indium tin oxide (ITO) with a thickness of as a thin film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, then dried, and UVO treatment was performed using UV in a UV cleaner for 5 minutes. After that, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum for ITO work function and residual film removal. Then, the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0478] On the transparent ITO electrode (anode), a hole injection layer of 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer of NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as a conventional layer.

[0479] The light-emitting layer was thermally vacuum deposited on the hole transport layer as follows. As the light-emitting layer, the heterocyclic compound described in Table 11 below was deposited to as a host, and as a green phosphorescent dopant, Ir(ppy)3 was doped and deposited at 7% relative to the deposition thickness of the light-emitting layer. After that, BCP was deposited to as a hole blocking layer, and Alq3 was deposited on the hole blocking layer to as an electron transport layer. Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) to the thickness, and then a cathode was formed on the electron injection layer by depositing aluminum (Al) cathode to the thickness, and as a result, an organic electroluminescent device was fabricated.

[0480] Meanwhile, for each material to be used in OLED fabrication, all the organic compounds required for fabricating OLED were vacuum sublimation purified under 10 -8 torr to 10 -6 torr.

[0481] For each of the organic electroluminescent devices fabricated as above, the electroluminescence (EL) characteristics were measured using M7000 manufactured by McScience Inc., and for the measurement results, T was measured by a lifetime measurement system (M6000) manufactured by McScience Inc. at a standard brightness of 6,000 cd / m 2 when90 .

[0482] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the above-manufactured organic light-emitting device are shown in Table 11 below.

[0483] [Table 11]

[0484]

[0485]

[0486]

[0487] <Experimental Example 2>-Fabrication of Organic Light-Emitting Device

[0488] A glass substrate coated with ITO having a thickness of as a thin film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, then dried, and subjected to UVO treatment for 5 minutes using UV in a UV cleaner. After that, the substrate was transferred to a plasma cleaner (PT), and plasma treatment was performed under vacuum for ITO work function and residual film removal, and then the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0489] On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as a conventional layer.

[0490] The light-emitting layer was thermally vacuum deposited on the hole transport layer as follows. As the light-emitting layer, one type of compound described in Chemical Formula 1 and one type of compound described in Chemical Formula 2 were premixed and deposited in one supply source to as the host, and as a green phosphorescent dopant, Ir(ppy)3 was doped and deposited at 7% with respect to the deposition thickness of the light-emitting layer. After that, BCP was deposited to as a hole blocking layer, and Alq3 was deposited on the hole blocking layer to as an electron transport layer.

[0491] Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) to the thickness, and then a cathode was formed on the electron injection layer by depositing aluminum (Al) cathode to the thickness, and as a result, an organic electroluminescent device was fabricated.

[0492] Meanwhile, for each material to be used in OLED manufacturing, all the organic compounds required for manufacturing OLEDs are purified by vacuum sublimation at pressures ranging from 10 -8 torr to 10 -6 torr.

[0493] For each of the organic electroluminescent devices manufactured as described above, the electroluminescence (EL) characteristics are measured using an M7000 manufactured by McScience Inc., and for the measurement results, the lifetime is measured by a lifetime measurement system (M6000) manufactured by McScience Inc. at a standard brightness of 6,000 cd / m 2 ². 90

[0494] The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light-emitting devices manufactured according to the present disclosure are shown in Table 12 below.

[0495] [Table 12]

[0496]

[0497]

[0498]

[0499]

[0500] As can be seen from the results in Table 12, compared with Comparative Examples 20 to 30, the organic electroluminescent devices using the light-emitting layer materials of the organic electroluminescent devices of the present disclosure have a lower driving voltage, improved luminous efficiency, and also have a significantly improved lifetime.

[0501] From the results in Table 11 (each separately containing the compound) and Table 12 (simultaneously containing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2), it can be seen that when the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are simultaneously contained, effects or more excellent efficiency and lifetime are obtained. Such results can lead to the prediction that an exciplex phenomenon occurs when the two compounds are simultaneously contained.

[0502] In particular, Table 11 shows the organic light-emitting devices each separately containing Chemical Formula 1 or Chemical Formula 2 of the present application, and it is determined that especially when Chemical Formula 2 is used alone, very poor performance is obtained, and it is determined that by combining Chemical Formula 1 of the present application and Chemical Formula 2 of the present application as in Table 12, higher-level performance is achieved by forming an exciplex form, enhancing hole transport ability, and reducing the resistance to receiving holes from the hole transport layer.

[0503] The exciplex phenomenon is a phenomenon in which energy of the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) is released due to electron exchange between two molecules. When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, and thus, the internal quantum efficiency of fluorescence can be increased up to 100%. When a donor (p-host) having good hole transport ability and an acceptor (n-host) having good electron transport ability are used as the host of the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, and thus the driving voltage can be reduced, which contributes to an improvement in lifetime. In the disclosure of the present application, it was determined that excellent device characteristics were obtained when a heterocyclic compound of Chemical Formula 2 acting as a donor and a heterocyclic compound of Chemical Formula 1 acting as an acceptor were used as the light-emitting layer host.

[0504] The structure of Chemical Formula 1 in the disclosure of the present application is such a structure: the structure has a high electronegativity and has a more stable structure containing dibenzofuran and dibenzothiophene and a fused arylene group. The structure also has a high electron mobility, and thus receives electrons from the electron transport layer and transports the electrons to the dopant, and forms an exciplex with the p-type host (electron donor) to have higher efficiency through reverse intersystem crossing. In particular, it was determined that even in an environment where reverse intersystem crossing occurs, high structural stability and a longer lifetime in which the fused ring group has delayed material deterioration even when many electrons are introduced into the light-emitting layer were obtained.

[0505] In addition, in the present disclosure, a light-emitting host formed of a plurality of types of compounds is deposited after being premixed and formed in one supply source (Experimental Example 2, Table 12). Here, since multiple depositions are not performed, there is an advantage of completely maintaining the uniformity of the film surface and film characteristics. In addition, by simplifying the process, a device having improved efficiency, driving voltage, and lifetime can be obtained, and the overall process cost can be reduced.

[0506] As can be seen from Table 12, the fused carbazole structure of the heterocyclic compound of Chemical Formula 2 in the present application is a structure containing two carbazoles or one carbazole and a heterocycle, and has strong electron donor characteristics due to the non-bonding electron pairs present in the nitrogen of carbazole and the heteroatom. In other words, as can be seen from Table 12, it was determined that the overall driving voltage / efficiency / lifetime is excellent compared to when using one of the heterocyclic compound corresponding to Chemical Formula 1 in the present application and the compounds corresponding to Compounds A to E (bicarbazole type; or a structure in which carbazole is bonded to a heterocycle).

[0507] In addition, compared with non-fused carbazole compounds, a wide-region HOMO energy level is obtained through π-conjugation over a wide region corresponding to the entire basic skeleton, and a wider hole distribution is obtained. Therefore, the property of fast hole transport is determined when driving the device, and thereby, the advantages of improving the current efficiency by reducing the driving voltage of the device and reducing the threshold voltage are determined.

[0508] In addition, the fused carbazole in Chemical Formula 2 has a form in which a pentagonal ring to a hexagonal ring are fused through π-π bonds. It has a structure (rigid structure) containing the smallest intramolecular distortion, thereby showing high thermal stability (T d95 : 400 °C or higher, high T g ). The high thermal stability is advantageous in overcoming the severe high-vacuum and high-temperature conditions of the deposition process of the organic light-emitting device (OLED), and is also advantageous in resisting device degradation when driving the device for a long time. Therefore, it is seen that the fused carbazole structure as the same as the structure of Chemical Formula 2 can be a basic structure of a material with a good lifetime based on low voltage, high efficiency, and high thermal stability.

[0509] In addition, when pre-mixing is performed as in Table 12, it is necessary to check the unique thermal properties of each material before mixing. Herein, according to the unique thermal properties of the materials, depositing the pre-mixed host material from one supply source can greatly affect the deposition conditions (including the deposition rate). When the thermal properties between two or more types of pre-mixed materials are not similar and are very different, repeatability and reproducibility may not be maintained during the deposition process, which means that it may not be possible to fabricate all-uniform OLEDs in one deposition process.

[0510] To overcome this problem, the electrical properties of the materials can be adjusted by using an appropriate combination of the basic structure and substituents of each material, and in addition to this, the thermal properties of the materials can be controlled according to the molecular structure form. Therefore, by using various substituents other than the basic skeleton in Chemical Formula 2 and using the C-N bonding of the fused carbazole as in Chemical Formula 2, the diversification of various pre-mixed deposition processes between hosts can be ensured by controlling the thermal properties of each material and attempting to improve the device performance. This has the advantage of ensuring the diversification of pre-mixed deposition processes using three, four, or more host materials and two compounds as hosts.

[0511] In addition, when driving an OLED, the interior of the device is exposed to various types of heat for a long time due to the heat energy generated by non-radiative emission caused by long-term driving of the device and the heat energy generated by the resistance to current. Different from metals, organic materials have very low thermal resistance, and thus precise thermal stability data is required to ensure the thermal stability of the materials. In addition, the deposition process of the OLED device is also carried out at high temperature under high vacuum, and materials with low thermal stability have deteriorated during the deposition process and may not be able to drive the OLED at all. Therefore, when constructing an OLED, it is very important preliminary work to check the thermal stability of the materials forming the device.

[0512] The fused carbazole structure described in Chemical Formula 2 has a form in which several pentagonal rings / hexagonal rings fused by bond strength are connected, and has a very rigid structure, and thus has a high Tg of 100 °C or higher and a very high Td(95%) of 400 °C or higher. It can be seen therefrom that the material can fully withstand the harsh high vacuum / high temperature state of the OLED deposition process and has sufficient stability to prevent device deterioration even after long-term driving of the device.

[0513] Figures 4 to 21 are the thermal analysis data of each material of Chemical Formula 2 measured using a TGA / DSC device of Mettler Toledo. The measured Td is measured while raising the temperature from 30 °C to 600 °C at a rate of 10 K per minute by heating. 95 Among the thermal properties corresponding to Chemical Formula 2 such as glass transition temperature (Tg), crystallization temperature (Tc), melting temperature (Tm) and decomposition temperature (Td / 95%), the stability of the long-term driving and high vacuum deposition processes of the device is first determined by checking the glass transition temperature and decomposition temperature.

[0514] Figure 4 and Figure 5 are graphs showing the thermal stability of Compound 2-19 of the present application, Figure 6 and Figure 7 are graphs showing the thermal stability of Compound 2-20 of the present application, Figure 8 and Figure 9 are graphs showing the thermal stability of Compound 2-22 of the present application, Figure 10 and Figure 11 are graphs showing the thermal stability of Compound 2-8 of the present application, Figure 12 and Figure 13 are graphs showing the thermal stability of Compound 2-18 of the present application, Figure 14 and Figure 15 are graphs showing the thermal stability of Compound 2-79 of the present application, and Figure 16 andFigure 17 This is a graph showing the thermal stability of Compound 2-123 of the present application.

[0515] In addition, Figure 18 and Figure 19 This is a graph showing the thermal stability of Compound A, and Figure 20 and Figure 21 This is a graph showing the thermal stability of Compound C.

[0516] In the graph showing thermal stability, Figures 4 to 21 Td 95 is the point at which the temperature is measured when 95% of the mass remains after applying the temperature, and when Td 95 is high, it means that it is stable even at high temperatures.

[0517] As determined by comparing Figures 4 to 17 and Figures 18 to 21 it is determined that in Compound A having a dicarbazole structure ( Figure 18 and Figure 19 ) and Compound C ( Figure 20 and Figure 21 ), Td 95 is measured to be 400 °C or lower, which shows lower thermal stability compared to the fused carbazole compound.

[0518] Therefore, it is determined that the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 simultaneously included are a basic structure that is sufficiently effective for manufacturing a device for the purpose of low voltage / high efficiency or an OLED having characteristics of high efficiency / long life or low voltage / long life.

Claims

1. An organic light-emitting device, comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain a heterocyclic compound represented by the following Chemical Formula 1 and a heterocyclic compound represented by any one of the following Chemical Formulas 2-7 to 2-9: [Chemical Formula 1] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9] In Chemical Formulas 1 and 2-7 to 2-9, N-Het is a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group containing one or more Ns; L and L1 are a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar1 is a substituted or unsubstituted C10 to C60 aryl group, or is represented by the following Chemical Formula 1-A; [Chemical Formula 1-A] X1 is O; S; or NR22; R1 to R4 are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring; A3 is O; S; or NRg; R50 and R51 are hydrogen; phenyl; or triphenylene; Rg is a substituted or unsubstituted C6 to C60 aryl group; R11, R14, R52 and R53 are hydrogen; r is an integer from 0 to 3; q is an integer from 0 to 4; R5 to R7 are the same as or different from each other, and are each independently selected from: hydrogen; deuterium; halogen; cyano; 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; and -NRR'; A1 and A2 are the same as or different from each other, and are each independently O; S; NRa; or CRbRc; R22, R, R' and R" are the same as or different from each other, and are each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Ra is phenyl unsubstituted or substituted with one or more substituents selected from phenyl, biphenyl and triphenylsilyl; biphenyl; naphthyl; terphenyl; triphenylene; dimethylfluorenyl; diphenylfluorenyl; dibenzofuranyl; dibenzothiophenyl; or carbazolyl unsubstituted or substituted with phenyl; Rb and Rc are the same as or different from each other, and each independently is a C1-C20 alkyl group; b, c, and d are integers from 0 to 3; and a and e are integers from 0 to 5, "Substituted or unsubstituted" means substituted with one or more substituents selected from: C1-C60 linear or branched alkyl groups; C6-C60 monocyclic or polycyclic aryl groups; C2-C60 monocyclic or polycyclic heteroaryl groups; -SiRR'R''; and -P(=O)RR', or substituted with substituents connected by two or more substituents selected from the substituents shown above, or is unsubstituted.

2. The organic light-emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 3 to 6: [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] In Chemical Formulas 3 to 6, N-Het, L, L1, R1 to R7, X1, and a to e have the same definitions as in Chemical Formula 1.

3. The organic light-emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 6-1: [Chemical Formula 3-1] [Chemical Formula 4-1] [Chemical Formula 5-1] [Chemical Formula 6-1] In Chemical Formulas 3-1 to 6-1, N-Het, L, L1, R6, R7, a to c, and e have the same definitions as in Chemical Formula 1; and Ar2 is a substituted or unsubstituted monocyclic or polycyclic C10-C60 aryl group.

4. The organic light-emitting device according to claim 1, wherein Chemical Formula 1-A is represented by any one of the following Chemical Formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In Chemical Formulas 1-1 to 1-6, X1, R5, and d have the same definitions as in Chemical Formula 1; Refers to the position linked to L1 of Chemical Formula 1; R31 to R34 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; and R35 and R36 are the same as or different from each other, and each independently is hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

5. The organic light-emitting device according to claim 1, wherein N-Het is any one of the following structural formulas: In the said structural formula, refers to the position linked to L of Chemical Formula 1; and R41 to R45 are the same as or different from each other, and each independently is hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

6. The organic light-emitting device according to claim 1, wherein R5 to R7 are hydrogen.

7. The organic light-emitting device according to claim 1, wherein R11 and R14 to R19 of Chemical Formula 2 are hydrogen.

8. The organic light-emitting device according to claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

9. The organic light-emitting device according to claim 1, wherein any one of Chemical Formulas 2-7 to 2-9 is represented by any one of the following compounds:

10. The organic light-emitting device according to claim 1, wherein the organic material layer includes at least one of a hole blocking layer, an electron injection layer, and an electron transport layer, and at least one of the hole blocking layer, the electron injection layer, and the electron transport layer contains a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by any one of Chemical Formulas 2-7 to 2-9.

11. The organic light-emitting device according to claim 1, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer contains a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by any one of Chemical Formulas 2-7 to 2-9.

12. The organic light-emitting device according to claim 1, wherein the organic material layer includes a light-emitting layer, the light-emitting layer contains a host material, and the host material contains a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by any one of Chemical Formulas 2-7 to 2-9.

13. The organic light-emitting device according to claim 1, further comprising one, two, 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.

14. A composition for an organic material layer of an organic light-emitting device, the composition comprising: a heterocyclic compound represented by the following Chemical Formula 1; and a compound represented by any one of the following Chemical Formulas 2-7 to 2-9: [Chemical Formula 1] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9] Among them, In Chemical Formulas 1 and 2-7 to 2-9, N-Het is a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group containing one or more Ns; L and L1 are a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar1 is a substituted or unsubstituted C10 to C60 aryl group, or is represented by the following Chemical Formula 1-A; [Chemical Formula 1-A] X1 is O; S; or NR22; R1 to R4 are the same as or different from each other, and each independently is hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups bond to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring; A3 is O; S; or NRg; R50 and R51 are hydrogen; phenyl; or triphenylene; Rg is a substituted or unsubstituted C6 to C60 aryl group; R11, R14, R52, and R53 are hydrogen; r is an integer from 0 to 3; q is an integer from 0 to 4; R5 to R7 are the same as or different from one another, and each independently selected from: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C2-C60 alkenyl; substituted or unsubstituted C2-C60 alkynyl; substituted or unsubstituted C1-C60 alkoxy; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; substituted or unsubstituted C2-C60 heteroaryl; -P(=O)RR'; -SiRR'R"; and -NRR'; A1 and A2 are the same as or different from one another, and each independently is O; S; NRa; or CRbRc; R22, R, R' and R" are the same as or different from one another, and each independently is hydrogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl; Ra is phenyl unsubstituted or substituted with one or more substituents selected from phenyl, biphenyl and triphenylsilyl; biphenyl; naphthyl; terphenyl; triphenylene; dimethylfluorenyl; diphenylfluorenyl; dibenzofuranyl; dibenzothiophenyl; or carbazolyl unsubstituted or substituted with phenyl; Rb and Rc are the same as or different from one another, and each independently is C1-C20 alkyl; b, c and d are integers from 0 to 3; and a and e are integers from 0 to 5, "Substituted or unsubstituted" means substituted with one or more substituents selected from the following: C1-C60 linear or branched alkyl; C6-C60 monocyclic or polycyclic aryl; C2-C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; and -P(=O)RR', or substituted with a substituent formed by linking two or more of the substituents shown above, or is unsubstituted.

15. The composition for an organic material layer for an organic light-emitting device according to claim 14, wherein in the composition, the weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by any one of Chemical Formulas 2-7 to 2-9 is 1:10 to 10:

1.

16. A method for manufacturing an organic light-emitting device, the method comprising: Preparing a substrate; Forming a first electrode on the substrate; Forming one or more organic material layers on the first electrode; And Forming a second electrode on the organic material layer, wherein the formation of the organic material layer includes using the composition for an organic material layer according to claim 14 to form one or more organic material layers.

17. The method for manufacturing an organic light-emitting device according to claim 16, wherein the formation of the organic material layer is performed using a thermal vacuum deposition method after premixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of any one of Chemical Formulas 2-7 to 2-9.

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