Novel heterocyclic compound and organic light-emitting diode comprising same

Abstract

The present invention relates to a novel aromatic heterocyclic compound usable in an organic light-emitting diode and an organic light-emitting diode comprising same and, more specifically, to a novel aromatic heterocyclic compound and an organic light-emitting diode comprising same, wherein the novel aromatic heterocyclic compound, when used as a phosphorescent host material in a light-emitting layer of an organic light-emitting diode, enables the organic light-emitting diode to achieve lower voltage, higher efficiency, and longer lifespan characteristics compared with organic light-emitting diodes according to the prior art.

Description

Novel heterocyclic compound and organic light-emitting device comprising the same

[0001] The present invention relates to a novel compound that can be used in an organic light-emitting device, and more specifically, to a novel heterocyclic compound that can be used as a host material of a light-emitting layer in an organic light-emitting device, thereby realizing device characteristics of low voltage, high efficiency, and long lifespan, and an organic light-emitting device comprising the same.

[0002] Organic light emitting diodes (OLEDs) are displays that utilize the self-luminous phenomenon. They have advantages such as a large viewing angle, being thinner and simpler than liquid crystal displays, and having a fast response speed, and are expected to be applied to full-color displays or lighting.

[0003] In general, organic light emitting diodes (OLEDs) use organic materials to convert electrical energy into light energy. They typically have a structure comprised of an anode, a cathode, and an organic layer between them. The organic layer often comprises a multilayer structure composed of different materials to enhance the efficiency and stability of the OLED, including, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in this OLED, holes are injected into the organic layer from the anode and electrons from the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons drop back to their ground state, light is emitted. These OLEDs are known to exhibit characteristics such as self-luminescence, high brightness, high efficiency, low operating voltage, wide viewing angle, high contrast, and high-speed response.

[0004] Materials used as organic layers in organic light-emitting devices can be classified into luminescent materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. The luminescent materials can be classified into high molecular weight and low molecular weight types depending on their molecular weight, and can be classified into fluorescent materials derived from singlet excited states of electrons and phosphorescent materials derived from triplet excited states of electrons depending on their luminescence mechanism.

[0005] Meanwhile, when only one material is used as a light-emitting material, the maximum light-emitting wavelength shifts to a longer wavelength due to intermolecular interaction, resulting in a decrease in color purity or a decrease in device efficiency due to a light-emitting attenuation effect. Therefore, a host-dopant system can be used as a light-emitting material to increase color purity and light-emitting efficiency through energy transfer.

[0006] The principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, resulting in high-efficiency light emission. At this time, the wavelength of the host shifts to the wavelength of the dopant, so light of a desired wavelength can be obtained depending on the type of dopant used.

[0007] Among these light-emitting layers, heterocyclic compounds containing heteroatoms such as nitrogen and oxygen have been recently studied as host compounds for organic light-emitting devices utilizing phosphorescence. As a related prior art, Patent Publication No. 10-2020-0139834 (December 14, 2020) describes an organic light-emitting device that includes an aromatic heterocyclic compound with a polycyclic ring structure as a phosphorescent host.

[0008] However, despite the fact that various types of compounds have been manufactured for use in the light-emitting layer of organic light-emitting devices, including the above-mentioned conventional technology, there is still a continuous need for the development of novel compounds that can be applied to organic light-emitting devices and have device characteristics such as low-voltage operation, high efficiency, and long lifespan, and organic light-emitting devices including the same.

[0009] Therefore, the first technical task to be achieved by the present invention is to provide a novel organic compound that can be used as a phosphorescent host material in a light-emitting layer in an organic light-emitting device.

[0010] In addition, the second technical task to be achieved by the present invention is to provide an organic light emitting diode (OLED) having low voltage, high efficiency, and long lifespan, which includes the organic compound as a host material in the organic light emitting diode.

[0011] The present invention provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises a light-emitting layer including a host and a dopant; and wherein the host includes at least one heterocyclic compound of the following [chemical formula 1].

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] The above R1 to R 17are the same or different from each other, and each independently represents hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 7 to 30 carbon atoms A cycloalkyl group having a condensed ring, a cycloalkyl group having a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms, Any one selected from among an arylthio group of 30, a substituted or unsubstituted cycloalkylthio group of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group of 2 to 30 carbon atoms, a substituted or unsubstituted amine group of 0 to 40 carbon atoms, a substituted or unsubstituted silyl group of 0 to 40 carbon atoms, a substituted or unsubstituted germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0016] The above substituents R2 to R 17 At least one of them is a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms or a substituted or unsubstituted trypticenyl group,

[0017] One of the above substituents R2 to R5 is a single bond bonding to a nitrogen atom in the lower carbazole structure of the above chemical formula 1,

[0018] The above L is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, condensed with an aliphatic hydrocarbon ring.

[0019] The above m is 1 or 2, and in this case, when m is 2, each L is the same or different from each other,

[0020] In the above chemical formula 1, 'substitution' in 'substituted or unsubstituted' means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

[0021]

[0022] When the heterocyclic compound represented by the above chemical formula 1 according to the present invention is used as a phosphorescent host material in the light-emitting layer of an organic light-emitting device, it can provide an organic light-emitting device that can implement the characteristics of lower voltage, higher efficiency, and longer lifespan compared to an organic light-emitting device according to the prior art.

[0023] Figure 1 is a schematic diagram of an organic light-emitting device according to one specific example of the present invention.

[0024] Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the sizes and dimensions of structures are illustrated enlarged or reduced from the actual size to ensure clarity of the present invention, and well-known components are omitted to highlight characteristic components, so the present invention is not limited to the drawings.

[0025] In addition, since the size and thickness of each component shown in the drawings are arbitrarily shown for the convenience of explanation, the present invention is not necessarily limited to what is shown, and in order to clearly express various layers and regions in the drawings, the thicknesses are shown in an enlarged manner. And in the drawings, for the convenience of explanation, the thicknesses of some layers and regions are shown exaggeratedly. When it is said that a part such as a layer, film, region, or plate is "on" another part, this includes not only the case where it is "directly on" the other part, but also the case where there is another part in between.

[0026] Additionally, throughout the specification, when a part is said to "include" a component, this does not exclude other components, but rather implies the inclusion of other components, unless otherwise specifically stated. Furthermore, throughout the specification, "on" means located above or below the target part, and does not necessarily mean located above in the direction of gravity.

[0027]

[0028] The present invention provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises a light-emitting layer including a host and a dopant; and wherein the host includes at least one heterocyclic compound of the following [chemical formula 1].

[0029] [Chemical Formula 1]

[0030]

[0031] In the above chemical formula 1,

[0032] The above R1 to R 17are the same or different from each other, and each independently represents hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 7 to 30 carbon atoms A cycloalkyl group having a condensed ring, a cycloalkyl group having a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms, Any one selected from among an arylthio group of 30, a substituted or unsubstituted cycloalkylthio group of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group of 2 to 30 carbon atoms, a substituted or unsubstituted amine group of 0 to 40 carbon atoms, a substituted or unsubstituted silyl group of 0 to 40 carbon atoms, a substituted or unsubstituted germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0033] The above substituents R2 to R 17 At least one of them is a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms or a substituted or unsubstituted trypticenyl group,

[0034] One of the above substituents R2 to R5 is a single bond bonding to a nitrogen atom in the lower carbazole structure of the above chemical formula 1,

[0035] The above L is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, condensed with an aliphatic hydrocarbon ring.

[0036] The above m is 1 or 2, and in this case, when m is 2, each L is the same or different from each other,

[0037] In the above chemical formula 1, 'substitution' in 'substituted or unsubstituted' means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

[0038] In addition, the present invention provides a heterocyclic compound represented by the above chemical formula 1.

[0039]

[0040] Meanwhile, considering the range of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 5 to 50 carbon atoms', etc. in the present invention, the range of carbon atoms of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms respectively refers to the total number of carbon atoms constituting the alkyl moiety or aryl moiety when viewed as unsubstituted without considering the substituted portion of the substituent. For example, a phenyl group substituted with a butyl group at the para-position should be viewed as corresponding to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0041] The aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and when the aryl group has a substituent, it can be fused with an adjacent substituent to form an additional ring, and further, the aryl group can include an organic radical obtained by the removal of one hydrogen from an arene ring formed by the condensation of two arene rings.

[0042] Specific examples of the above aryl group include, but are not limited to, aromatic radical groups such as a phenyl group, an o-biphenyl group, an m-biphenyl group, a p-biphenyl group, an o-terphenyl group, an m-terphenyl group, a p-terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyl group, a chrysenyl group, a naphthacenyl group, a fluoranthenyl group, a triphenylenyl group, a trypticenylene group, and the like, and may also include an organic radical formed by the removal of one hydrogen from an arene ring formed by the condensation of two arene rings, such as an arene ring formed by the condensation of a fluorene ring and a phenylene ring, or an arene ring formed by the condensation of a fluorene ring and a phenanthrene ring.

[0043] In addition, at least one hydrogen atom of the aryl group is selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH2, -NH(R), -N(R')(R''), R' and R" are each independently an alkyl group having 1 to 10 carbon atoms, in which case it is referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 7 to 24 carbon atoms, an alkylaryl group having 7 to 24 carbon atoms, It may be substituted with a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 3 to 24 carbon atoms, or an alkylheteroaryl group having 3 to 24 carbon atoms.

[0044] In the present invention, the aromatic hydrocarbon ring means an aromatic ring composed of carbon and hydrogen, and further, the aliphatic hydrocarbon ring means a hydrocarbon ring composed of carbon and hydrogen but not belonging to an aromatic hydrocarbon ring, and at this time, the aliphatic hydrocarbon ring preferably has at least 30% or more of the carbon atoms forming the ring as sp 3 It may be a hydrocarbon ring that forms a bond through an orbital structure and contains 0 to 3 double bonds and / or triple bonds within the ring, and more preferably, at least 50% or more of the carbon atoms forming the ring are sp 3 It may be a hydrocarbon ring that is bonded by orbitals and contains 0 to 2 double bonds and / or triple bonds within the ring.

[0045] In addition, the aryl group in which the aliphatic hydrocarbon ring is condensed in the present invention means a cyclic substituent in which two adjacent carbon atoms in the aliphatic hydrocarbon ring and two adjacent carbon atoms excluding the carbon atom that becomes an organic radical by hydrogen removal from one of the carbon atoms forming the ring in the aryl group are condensed with each other to share one double bond and have overall non-aromaticity, and specific examples include, but are not limited to, a tetrahydronaphthyl group, a tetrahydrobenzocycloheptene, a tetrahydrophenanthrene group, a tetrahydroanthracenyl group, and an octahydrotriphenylene group.

[0046] The heteroaryl group, which is a substituent used in the compound of the present invention, refers to an aryl group of a ring aromatic system having 2 to 24 carbon atoms, which contains 1, 2 or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in an aromatic ring, and the remaining ring atoms are carbon, and the rings can be fused to form a ring. In addition, one or more hydrogen atoms in the heteroaryl group can be substituted with a substituent similar to that in the case of the aryl group.

[0047] Specific examples of the above heteroaryl group include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a pyrimidinyl group, a triazinyl group, a triazolyl group, an acridinyl group, a carbolinyl group, an acenaphthoquinoxalinyl group, an indenoquinazolinyl group, an indenoisoquinolinyl group, an indenoquinolinyl group, a pyridoindolyl group, a pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, Examples thereof include, but are not limited to, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoselenophene group, a dibenzothiophenyl group, a dibenzofuranyl group, a dibenzoselenophene group, a phenanthrolinyl group, a thiazolinyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenoxazinyl group, a phenothiazinyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzoselenophene group, and an indolocarbazole group.

[0048] In addition, in the present invention, the aromatic heterocycle means an aromatic hydrocarbon ring in which at least one aromatic carbon is substituted with a heteroatom, and the aromatic heterocycle may preferably be one in which 1 to 3 aromatic carbons in the aromatic hydrocarbon are substituted with at least one heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te.

[0049] In addition, the heteroaryl group having a condensed aliphatic hydrocarbon ring is a substituent having a structure in which a heteroaryl group is substituted instead of an aryl group in the condensed aliphatic hydrocarbon ring aryl group, and specific examples thereof include, but are not limited to, a tetrahydroindole group, a tetrahydrobenzofuranyl group, a tetrahydrobenzothiophene group, a tetrahydrocarbazole group, a tetrahydrodibenzofuranyl group, a tetrahydrobenzothiophene group, a tetrahydroquinoline group, and a tetrahydroquinoxaline group.

[0050] In addition, in the present invention, the aromatic heterocycle means an aromatic hydrocarbon ring in which at least one aromatic carbon is substituted with a heteroatom, and the aromatic heterocycle may preferably be one in which 1 to 3 aromatic carbons in the aromatic hydrocarbon are substituted with at least one heteroatom selected from among N, O, P, Si, S, Ge, Se, and Te.

[0051] In the present invention, the 'condensed ring in which an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring are condensed' means a condensed ring in which two adjacent carbon atoms in an aromatic hydrocarbon ring and two adjacent carbon atoms in an aliphatic hydrocarbon ring are condensed so that they are shared with each other, and examples thereof include tetrahydronaphthalene and dihydroindene rings in which two adjacent carbon atoms in a benzene ring and a cyclohexane ring are condensed so that they are shared with each other.

[0052] In addition, the 'condensed ring in which an aromatic heterocycle and an aliphatic hydrocarbon ring are condensed' in the present invention means a condensed ring in which two adjacent carbon atoms in an aromatic heterocycle and two adjacent carbon atoms in an aliphatic hydrocarbon ring are condensed so that they are shared with each other, and as an example, a hexahydrodibenzofuran ring in which two adjacent carbon atoms in each ring of a benzofuran ring and a cyclohexane ring are condensed so that they are shared with each other can be mentioned.

[0053] The alkyl group, which is a substituent used in the present invention, is a substituent in which one hydrogen is removed from an alkane, and has a structure including a straight chain or a branched chain. Specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and at least one hydrogen atom in the alkyl group can be replaced with a substituent similar to the case of the aryl group.

[0054] The halogenated alkyl group used as a substituent in the present invention means a substituent in which at least one hydrogen atom in the alkyl group as a substituent is replaced with a halogen group, and preferably, the halogen group may be a fluorine atom.

[0055] In the compound of the present invention, the 'cyclo' in the cycloalkyl group, cycloalkoxy group, etc., which are substituents, means a substituent having a structure capable of forming a single ring or multiple rings of a saturated hydrocarbon in the alkyl group or the alkoxy group, and for example, specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, bicycloheptanyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, isobornyl, etc., but are not limited thereto, and one or more hydrogen atoms in the cycloalkyl group can be substituted with a substituent similar to the case of the aryl group, and this can also be applied to cycloalkoxy.

[0056] Also, in the present invention, the heterocycloalkyl group means that at least one of the carbon atoms in the ring of a substituent forming a cycloalkyl structure is substituted with a heteroatom, and preferably, 1 to 3 carbon atoms may be substituted with at least one heteroatom selected from N, O, P, S, Si, Ge, Se, and Te.

[0057] In addition, the cycloalkyl group in which the aromatic hydrocarbon ring or aromatic heterocycle is condensed means a cyclic substituent in which two adjacent carbon atoms within the aromatic hydrocarbon ring or aromatic heterocycle and two adjacent carbon atoms, excluding a carbon atom that becomes an organic radical by the removal of hydrogen from one of the carbon atoms forming the ring within the cycloalkyl group, are condensed with each other to share one double bond and exhibit overall non-aromaticity, and specific examples include, but are not limited to, tetrahydronaphthyl, tetrahydrophenanthrene, tetrahydroquinoline, tetrahydroquinoxaline, and cyclopentabenzofuran.

[0058] In addition, the heterocycloalkyl group in which the aromatic hydrocarbon ring is condensed means a cycloalkyl group in which at least one of the carbon atoms in the cycloalkyl ring is substituted with a heteroatom in the cycloalkyl group in which the aromatic hydrocarbon ring is condensed, and preferably, it is a substituent having a structure in which 1 to 3 carbons in the cycloalkyl ring are substituted with at least one heteroatom selected from N, O, P, S, Si, Ge, Se, and Te, and specific examples include, but are not limited to, a hexahydrodibenzofuranyl group, a hexahydrocarbazole group, a hexahydrodibenzothiophene group, and a dihydrobenzodioxine group, and overall, it exhibits non-aromaticity.

[0059] In addition, the aryl group or heteroaryl group to which an aliphatic heterocycle is condensed is a substituent having a structure in which an aliphatic heterocycle is condensed instead of an aliphatic hydrocarbon ring in the aryl group or heteroaryl group to which an aliphatic hydrocarbon ring is condensed, and specific examples thereof include, but are not limited to, a chroman group, a dihydropyranopyridine group, a thiochroman group, a dihydrobenzodioxine group, a dihydrothiopyranopyridine group, and a dihydropyranopyrimidine group, and the like, and overall, exhibits non-aromaticity.

[0060] In addition, the above aliphatic heterocycle means that at least one of the carbons in the aliphatic hydrocarbon ring is replaced with a heteroatom, and the above aliphatic heterocycle may preferably be such that 1 to 3 carbons in the aliphatic hydrocarbon ring are replaced with at least one heteroatom selected from N, O, S, etc.

[0061] The alkoxy group, which is a substituent used in the compound of the present invention, is a substituent in which an oxygen atom is bonded to the terminal of an alkyl group or a cycloalkyl group, and specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantaneoxy, dicyclopentaneoxy, bornyloxy, isobornyloxy, etc., but are not limited thereto, and one or more hydrogen atoms of the alkoxy group may be substituted with a substituent similar to the case of the aryl group.

[0062] Specific examples of the arylalkyl group, which is a substituent used in the compound of the present invention, include, but are not limited to, phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl, naphthylethyl, etc., and at least one hydrogen atom of the arylalkyl group may be substituted with a substituent similar to that of the aryl group.

[0063] Specific examples of the alkylaryl group, which is a substituent used in the compound of the present invention, include, but are not limited to, tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, t-butylphenanthryl, etc., and at least one hydrogen atom of the alkylaryl group may be substituted with a substituent similar to that of the aryl group.

[0064] Additionally, in the present invention, an alkenyl group means an alkyl substituent including one carbon-carbon double bond formed by two carbon atoms, and an alkynyl group means an alkyl substituent including one carbon-carbon triple bond formed by two carbon atoms.

[0065] In addition, the alkylene group used in the present invention is an organic radical derived by the removal of two hydrogens in an alkane molecule, which is a saturated hydrocarbon in a straight or branched form. Specific examples of the alkylene group include, but are not limited to, a methylene group, an ethylene group, a propylene group, an isopropylene group, an isobutylene group, a sec-butylene group, a tert-butylene group, a pentylene group, an iso-amylene group, a hexylene group, and the like. One or more hydrogen atoms in the alkylene group may be replaced with a substituent similar to the case of the aryl group.

[0066] In addition, in the present invention, the amine group includes -NH2, and at least one of the two hydrogen atoms bonded to the nitrogen atom in the -NH2 is a functional group substituted with any one selected from an alkyl group, a cycloalkyl group, an aryl group, an aryl group having a condensed aliphatic hydrocarbon ring, an arylalkyl group, an alkylaryl group, a heteroaryl group, and a heteroaryl group having a condensed aliphatic hydrocarbon ring, and when both hydrogen atoms bonded to the nitrogen atom in the -NH2 are each substituted with the aforementioned substituents, each of these substituents may be the same as or different from each other, and at least one hydrogen atom in the alkyl group, cycloalkyl group, aryl group, aryl group having a condensed aliphatic hydrocarbon ring, arylalkyl group, alkylaryl group, heteroaryl group, and heteroaryl group having a condensed aliphatic hydrocarbon ring, bonded to the nitrogen atom in the amine group, may be substituted with a substituent similar to the case of the aryl group.

[0067] Here, each aryl group in the aryl group, arylheteroaryl group, aryl group with a condensed aliphatic hydrocarbon ring, cycloalkylaryl group, etc., bonded to the nitrogen atom of the amine group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the heteroaryl group, arylheteroaryl group, etc. may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0068] Examples of the above amine group include an alkylamine group in which one or two identical or different alkyl groups are bonded to a nitrogen atom, an arylamine group in which one or two identical or different aryl groups are bonded to a nitrogen atom, an alkylarylamine group in which one alkyl group and one aryl group are bonded to a nitrogen atom, and the like. In addition, there may be mentioned a heteroarylamine group, an arylheteroarylamine group, an alkyl (aryl in which an aliphatic hydrocarbon ring is condensed) amine group, an aryl (aryl in which an aliphatic hydrocarbon ring is condensed) amine group, a cycloalkyl (aryl in which an aliphatic hydrocarbon ring is condensed) amine group, a cycloalkylarylamine group, a heteroaryl (aryl in which an aliphatic hydrocarbon ring is condensed) amine group, and the like.

[0069]

[0070] The silyl group, which is a substituent used in the compound of the present invention, includes -SiH3, and at least one of the three hydrogen atoms bonded to the silicon atom in the -SiH3 is a functional group substituted with any one selected from an alkyl group, a cycloalkyl group, an aryl group, an aryl group having a condensed aliphatic hydrocarbon ring, an arylalkyl group, an alkylaryl group, a heteroaryl group, and a heteroaryl group having a condensed aliphatic hydrocarbon ring, and when one, two, or three hydrogen atoms bonded to the silicon atom in the -SiH3 are each substituted with the above substituents, each of these substituents may be the same as or different from each other, and at least one hydrogen atom in the alkyl group, cycloalkyl group, aryl group, aryl group having a condensed aliphatic hydrocarbon ring, arylalkyl group, alkylaryl group, heteroaryl group, and heteroaryl group having a condensed aliphatic hydrocarbon ring, bonded to the silicon atom in the silyl group, may be substituted with the same substituent as in the case of the aryl group. do.

[0071] Here, each aryl group in the aryl group, arylheteroaryl group, aryl group with a condensed aliphatic hydrocarbon ring, cycloalkylaryl group, etc., bonded to the silicon atom of the silyl group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the heteroaryl group, arylheteroaryl group, etc. may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0072] Examples of the above silyl group include an alkylsilyl group in which one or two or three identical or different alkyl groups are bonded to a silicon atom, an arylsilyl group in which one or two or three identical or different aryl groups are bonded to a silicon atom, an alkylarylsilyl group in which one alkyl group and one aryl group are bonded to a silicon atom, an alkylarylheteroarylsilyl group in which one alkyl group, one aryl group, and one heteroaryl group are bonded to a silicon atom, and in addition, an alkyl (heteroaryl) silyl group, an aryl heteroarylsilyl group, an alkyl (aryl with a condensed aliphatic hydrocarbon ring) silyl group, an alkyl (aryl with a condensed aliphatic hydrocarbon ring) silyl group, an alkyl (aryl with a condensed aliphatic hydrocarbon ring) silyl group, a cycloalkyl (aryl with a condensed aliphatic hydrocarbon ring) silyl group, a cycloalkylarylheteroarylsilyl group, an alkyl (heteroaryl) (aryl with a condensed aliphatic hydrocarbon ring) silyl group. You can hear the back.

[0073] In addition, specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc.

[0074] In addition, in the present invention, the germanium group (or low-mili group, or germanium group) means a functional group in which a germanium (Ge) atom is substituted for a silicon (Si) atom in the silyl group, and the remaining part follows what was described for the silyl group.

[0075] In addition, specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, dimethylfurylgermane, etc.

[0076] In addition, in the present invention, the substituent (A) in the aromatic ring and the "mutually adjacent substituent (B)" mean the substituent (B) bonded to the aromatic ring carbon atom(s) adjacent to the aromatic ring carbon atom to which the substituent A in the aromatic ring is bonded, and further, the substituent (A) in the alicyclic ring and the "mutually adjacent substituent (B)" mean the substituent (B) bonded to the ring carbon atom(s) adjacent to the ring carbon atom to which the substituent A in the alicyclic ring is bonded, and further, the substituent (A) bonded to a specific carbon atom in the aliphatic chain structure and the "mutually adjacent substituent (B)" mean the substituent (B) bonded to the carbon atom(s) adjacent to the specific carbon atom to which the substituent A in the aliphatic chain structure is bonded.

[0077]

[0078] Meanwhile, more preferable examples of 'substitution' in the 'substituted or unsubstituted' in the above chemical formula 1 include deuterium, tritium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 12 carbon atoms, a halogenated alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heteroalkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, an alkylaryl group having 7 to 20 carbon atoms, a heteroaryl group having 2 to 18 carbon atoms, a heteroarylalkyl group having 3 to 18 carbon atoms, an alkylheteroaryl group having 3 to 18 carbon atoms, and a alkylheteroaryl group having 9 to It may be substituted with one or more substituents selected from the group consisting of a cycloalkyl group having a condensed aromatic hydrocarbon ring, a cycloalkyl group having a condensed aromatic heterocycle having 7 to 20 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 9 to 20 carbon atoms, an aryl group having a condensed aliphatic hydrocarbon ring having 9 to 20 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 7 to 20 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an amine group having 1 to 18 carbon atoms, a silyl group having 1 to 18 carbon atoms, a germanium group having 1 to 18 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylthionyl group having 6 to 18 carbon atoms, and at least one hydrogen in each of the above substituents is replaced with deuterium or tritium. It is replaceable.

[0079] In addition, in the present invention, a more preferable example of the cycloalkyl group having a condensed aromatic hydrocarbon ring having 7 to 30 carbon atoms, which is substituted or unsubstituted, may be a cycloalkyl group having a condensed aromatic hydrocarbon ring having 9 to 20 carbon atoms, which is substituted or unsubstituted.

[0080] In addition, in the present invention, a more preferable example of the cycloalkyl group having a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms may be a cycloalkyl group having a substituted or unsubstituted aromatic heterocycle having 7 to 20 carbon atoms.

[0081] In addition, in the present invention, a more preferable example of the heterocycloalkyl group having a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms is a heterocycloalkyl group having a substituted or unsubstituted aromatic hydrocarbon ring having 9 to 20 carbon atoms.

[0082] In addition, in the present invention, a more preferable example of the aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is an aryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 9 to 20 carbon atoms.

[0083] In addition, in the present invention, a more preferable example of the heteroaryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms is a heteroaryl group having a substituted or unsubstituted aliphatic hydrocarbon ring having 7 to 20 carbon atoms.

[0084] In addition, in the present invention, a more preferable example of the aryl group having a substituted or unsubstituted carbon number of 6 to 30, aliphatic heterocycle condensed therein may be an aryl group having a substituted or unsubstituted carbon number of 7 to 20, aliphatic heterocycle condensed therein.

[0085] In addition, in the present invention, a more preferable example of the heteroaryl group having a substituted or unsubstituted carbon number of 5 to 30, aliphatic heterocycle condensed therein may be a heteroaryl group having a substituted or unsubstituted carbon number of 6 to 20, aliphatic heterocycle condensed therein.

[0086] Meanwhile, within the specification of the present invention, the 'substituent R 31Inland R 37 In the case of ', it can be connected to the above A1 to A3 rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, and this is R 31 Inland R 37 This means that a ring can be additionally formed by removing one hydrogen radical from each of the substituents in and also removing the hydrogen radical bonded to the carbon atom in the A1 to A3 rings and connecting them to each other.

[0087] In addition, within the specification of the present invention, the 'R 32 Wow R 33 , R 34 Wow R 35 and R 36 and R 37 Each of them can be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring, and in the case of ', this is R 32 Wow R 33 , R 34 Wow R 35 and R 36 and R 37 Corresponding to This means that an additional ring can be formed by removing one hydrogen radical from each of the two substituents and connecting them.

[0088]

[0089] In the present invention, the heterocyclic compound represented by the above chemical formula 1 comprises two carbazole structures, wherein a nitrogen atom in the lower carbazole is connected to a carbon atom in the benzene ring of the upper carbazole, and at least one of the carbon atoms in the benzene ring of each of the two carbazoles is technically characterized by being bonded to a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms or a substituted or unsubstituted trypticenyl group.

[0090] Here, preferably, the substituents R2 to R 17At least one of the groups may be a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms or a substituted or unsubstituted trypticenyl group, more preferably a substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms or a substituted or unsubstituted trypticenyl group, and more preferably a deuterium-substituted or unsubstituted cycloalkyl group having 5 to 20 carbon atoms or a substituted or unsubstituted trypticenyl group.

[0091]

[0092] Meanwhile, the triptycenyl group included in the chemical formula 1 of the present invention means an organic radical in which a hydrogen atom bonded to one carbon atom in a triptycene ring (see Figure A below) corresponding to an aromatic hydrocarbon ring is removed.

[0093] <Figure A: Trypticene ring>

[0094] Here, when the substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms or the substituted or unsubstituted trypticenyl group is bonded to the benzene ring in the two carbazole structures represented by the above chemical formula 1 of the present invention, the two carbazole structures of the above chemical formula 1 have a bulky substituent, so that a relatively high T g Since it has a value and has the effect of reducing intermolecular attraction, it can suppress the diffusion of triplet excitons generated in the light-emitting layer to adjacent organic layers, hole transport layers, or electron transport layers, and thus has the advantage of providing the effects of low voltage, high efficiency, and long life when used as a host material in an organic light-emitting device.

[0095]

[0096] As a more preferred embodiment of the present invention, the heterocyclic compound according to the present invention comprises R in the chemical formula 1 10 Inland R 17At least one of them may be a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms or a substituted or unsubstituted trypticenyl group, and in this case, as a more preferable example of the 'substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms and substituted or unsubstituted trypticenyl group', it may be any one selected from the following structural formulae 1 to 4.

[0097] [Structural formula 1] [Structural formula 2] [Structural formula 3] [Structural formula 4]

[0098]

[0099] Here, one carbon atom in the cycloalkane ring structure in the structural formulas 1 to 3 is a radical from which hydrogen has been removed and is bonded to a carbon atom in the benzene ring of the carbazole structure in the chemical formula 1, and one aromatic carbon atom in the trypticene ring in the structural formula 4 is a radical from which hydrogen has been removed and is bonded to a carbon atom in the benzene ring of the carbazole structure in the chemical formula 1,

[0100] The hydrogen site bonded to the carbon atom in the above structural formulas 1 to 4 may be bonded to any one selected from hydrogen and deuterium.

[0101] In addition, as an embodiment of the present invention, R in the chemical formula 1 10 Inland R 17 In the case where at least one of the above structural formulas 1 to 4 is selected, the heterocyclic compound according to the present invention may be a single bond in which the substituent R4 among the substituents R2 to R5 in the chemical formula 1 is bonded to a nitrogen atom, and in this case, more preferably, the substituent R 10 Inland R 17 Only one of them may be selected from the structural formulas 1 to 4.

[0102] In addition, as a more preferred embodiment of the present invention, R in the chemical formula 1 10 Inland R 17In the case where only one of the above structural formulas 1 to 4 is selected, and the substituent R4 among the substituents R2 to R5 is a single bond bonding to a nitrogen atom, the R2 to R 17 Among them, the substituents other than the substituents selected from structural formulas 1 to 4 are the same or different from each other, and can each be independently any one selected from hydrogen and deuterium, and in this case, more preferably, the substituent R1 can be a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, and in this case, more preferably, the substituent R1 can be a substituent represented by the following structural formula A.

[0103] [Structural formula A]

[0104]

[0105] In the above structural formula A

[0106] L1 to L3 are the same or different from each other, and each independently represents one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and an arylene group having a substituted or unsubstituted aliphatic hydrocarbon ring condensed therein, more preferably, a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 18 carbon atoms, and an arylene group having a substituted or unsubstituted aliphatic hydrocarbon ring condensed therein.

[0107] The above Ar1 to Ar3 are the same or different from each other, and each independently can be any one selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms, which is condensed with an aliphatic hydrocarbon ring, more preferably, any one selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 20 carbon atoms, which is condensed with an aliphatic hydrocarbon ring,

[0108] In the above structural formula A, '*' indicates a binding site that binds to the linker L in chemical formula 1.

[0109] As a more preferred embodiment, the substituents R2 to R in the chemical formula 1 17 are the same or different from each other, and each independently may be any one selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 8 to 20 carbon atoms, a condensed aliphatic hydrocarbon ring, and a substituted or unsubstituted amine group having 1 to 30 carbon atoms.

[0110] In addition, as a specific example of the heterocyclic compound represented by the chemical formula 1 in the present invention, it may be any one selected from compounds 1 to 60 below, but is not limited thereto.

[0111]

[0112] Compound 1 Compound 2 Compound 3

[0113]

[0114] Compound 4 Compound 5 Compound 6

[0115]

[0116] Compound 7 Compound 8 Compound 9

[0117]

[0118] Compound 10 Compound 11 Compound 12

[0119]

[0120] Compound 13 Compound 14 Compound 15

[0121]

[0122] Compound 16 Compound 17 Compound 18

[0123]

[0124] Compound 19 Compound 20 Compound 21

[0125]

[0126] Compound 22 Compound 23 Compound 24

[0127]

[0128] Compound 25 Compound 26 Compound 27

[0129]

[0130] Compound 28 Compound 29 Compound 30

[0131]

[0132] Compound 31 Compound 32 Compound 33

[0133]

[0134] Compound 34 Compound 35 Compound 36

[0135]

[0136] Compound 37 Compound 38 Compound 39

[0137]

[0138] Compound 40 Compound 41 Compound 42

[0139]

[0140] Compound 43 Compound 44 Compound 45

[0141]

[0142] Compound 46 Compound 47 Compound 48

[0143]

[0144] Compound 49 Compound 50 Compound 51

[0145]

[0146] Compound 52 Compound 53 Compound 54

[0147]

[0148] Compound 55 Compound 56 Compound 57

[0149]

[0150] Compound 58 Compound 59 Compound 60

[0151]

[0152] As described above, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises a light-emitting layer comprising a host and a dopant, and wherein the host in the light-emitting layer comprises at least one heterocyclic compound according to the present invention as described above, and the organic light-emitting device according to the present invention can exhibit low-voltage operation, high efficiency, and long-life characteristics.

[0153] Here, in addition to the light-emitting layer, the organic layer may additionally include at least one layer selected from a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, an electron transport layer, an electron injection layer, a functional layer having both an electron injection function and an electron transport function, and a hole blocking layer.

[0154] Meanwhile, in the present invention, “(the organic layer) includes at least one organic compound” can be interpreted as “(the organic layer) can include one organic compound belonging to the category of the present invention or two or more different compounds belonging to the category of the organic compound.”

[0155] As a more preferred embodiment of the present invention, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode; wherein the organic layer comprises: a light-emitting layer including a host and a dopant; and at least one layer among a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer; wherein the host comprises at least one heterocyclic compound according to the present invention, and in this case, the heterocyclic compound represented by the chemical formula 1 according to the present invention can be used as a blue phosphorescent host.

[0156] In one embodiment of the present invention, the host in the light-emitting layer may additionally include at least one host compound different from the heterocyclic compound represented by the chemical formula 1, and for example, at least one different host compound may be mixed and deposited, co-deposited, or laminated and used. That is, the host according to the present invention may additionally include at least one additional host compound different from the compound represented by the chemical formula 1, and two or more host compounds may be mixed and deposited, co-deposited, or laminated and used. In the case of the laminate, a host compound different from the heterocyclic compound may be laminated on or under a layer including the heterocyclic compound according to the present invention.

[0157] Here, in the case of mixing and depositing a host compound different from the heterocyclic compound represented by the above-mentioned chemical formula 1, it means that they are mixed in one deposition source and deposited by sublimation or vaporization, and in the case of co-deposition, it means that two or more types of hosts are deposited together by sublimation or vaporization in each of multiple deposition sources.

[0158] That is, the method for forming the light-emitting layer may be to form a thin film by depositing (co-depositing) a plurality of host materials from different plurality of deposition sources, or to mix the plurality of hosts in advance and deposit the mixed host, or to form the light-emitting layer by a lamination method when depositing the host.

[0159] Here, in addition to one compound represented by the above chemical formula 1, at least one additional host compound is additionally included, and when two or more host compounds are mixed and deposited, co-deposited, or laminated, more preferably, a compound having an electron acceptor moiety can be used as the additional host, and due to the HOMO / LUMO levels of the high hole injection and electron injection barriers that are mixed and deposited, co-deposited, or laminated with the chemical formula 1 having an amine group as an electron donor moiety, the recombination region is limited to the interface of the two hosts, thereby minimizing current loss, and thus, a high-efficiency, long-life organic light-emitting device can be implemented.

[0160] At this time, the compound having the electron acceptor moiety is a compound having a moiety that has an environment that is easy to receive electrons from the outside, such as an azine compound which is a nitrogen-containing aromatic heterocycle such as pyridine, pyrimidine, triazine, etc. in the molecule, and a compound substituted with a cyano group (-CN), and preferably, may include a compound including a heteroaryl group including 1 to 3 N (nitrogen) in the molecule; or an aryl group including 1 to 3 cyano groups (-CN) in the molecule.

[0161] More specifically, the host in the light-emitting layer of the organic light-emitting device may include at least one organic compound represented by the following chemical formula 2 in addition to the heterocyclic compound represented by the above chemical formula 1. For example, at least one organic compound represented by the above chemical formula 2 may be mixed and deposited, co-deposited, or the organic compound represented by the following chemical formula 2 may be laminated on or under a layer including the heterocyclic compound represented by the above chemical formula 1.

[0162] [Chemical Formula 2]

[0163]

[0164] In the above [chemical formula 2],

[0165] X1 to X3 are identical or different and are each independently N or CR. 20 However, at least one of the above X1 to X3 is N, and at least two of the above X1 to X3 are CR 20 In each case, CR 20 are the same or different,

[0166] L 21 Inland L 23 are the same or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 20 carbon atoms, which is a condensed aliphatic hydrocarbon ring,

[0167] The above m 21 Inland m 23 are identical or different, and are each independently an integer from 1 to 2, provided that when they are 2, each L 21 Inland L 23 are each other Same or different,

[0168] R 21 Inland R 24are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, a substituted or An unsubstituted cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted Any one selected from an unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0169] In the above chemical formula 2, 'substitution' in 'substituted or unsubstituted' means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

[0170] As a more preferred embodiment of the present invention, in the chemical formula B, each of X1 to X3 is N, and R 21 Inland R 23 At least one of the groups may be a substituted or unsubstituted carbazole group.

[0171]

[0172] Meanwhile, in the present invention, the light-emitting layer may use a dopant material in addition to a host. When the light-emitting layer includes a host and a dopant, the content of the dopant may typically be selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0173] More specifically, the dopant in the light-emitting layer of the organic light-emitting device according to the present invention may be an organometallic compound containing a transition metal. In this case, the dopant is not a fluorescent dopant material that only transfers to a singlet state using the Förster energy transfer method in the existing Host-Dopant system, but includes a phosphorescent dopant material of a metal complex including at least one metal selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re, Pd, etc. that transfers without distinguishing between singlet and triplet states using the Dexter energy transfer method, and any known dopant material can be used without special limitation as long as it emits light from a triplet exciton.

[0174] The above dopant material is preferably a transition metal complex, and may be selected from Ir, Pt, Pd, etc., and specific examples include Ir(ppy)3, Ir(ppy)2acac, Ir(Bt)2acac, Ir(MDQ)2acac, Ir(mppy)3, Ir(piq). 3, Ir (piq)2acac, Ir (pq)2acac, Ir(mpp)2acac, F2Irpic, (F2ppy)2Ir(tmd), Ir(ppy)2tmd, Ir(pmi)3, Ir(pmb)3, FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP, Ir(chpy)3,P0-01(C 31 H 23 IrN2O2S2), Ir(ppz) 3,Ir(dfppz) 3, PtNON, Pt-10, Pt-11, etc. can be used, but are not limited thereto.

[0175]

[0176] In addition, the light-emitting layer may further include various hosts and various dopant materials in addition to the dopant and host, and preferably, the dopant in the light-emitting layer of the organic light-emitting device may include at least one dopant compound containing boron that is different from the organometallic compound containing the transition metal.

[0177] More specifically, the dopant in the light-emitting layer of the organic light-emitting device may additionally include a polycyclic ring compound represented by the following chemical formula 3 in addition to the organometallic compound containing the transition metal.

[0178] [Chemical Formula 3]

[0179]

[0180] In the above [chemical formula 3],

[0181] Y1 and Y2 are the same or different and are independently O, S, NR 31 , CR 32 R 33 , SiR 34 R 35 and GeR 36 R 37 One of the following is selected:

[0182] A1 to A3 are the same or different from each other, and are each independently selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, an aromatic hydrocarbon ring formed by condensing substituted or unsubstituted aliphatic hydrocarbon rings having 8 to 50 carbon atoms, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocycle formed by condensing substituted or unsubstituted aliphatic hydrocarbon rings having 5 to 50 carbon atoms.

[0183] The above R 31 Inland R 37are the same or different from each other, and each independently represents hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 7 to 30 carbon atoms A cycloalkyl group having a condensed ring, a cycloalkyl group having a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms, Any one selected from among an arylthio group of 30, a substituted or unsubstituted cycloalkylthio group of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group of 2 to 30 carbon atoms, a substituted or unsubstituted amine group of 0 to 40 carbon atoms, a substituted or unsubstituted silyl group of 0 to 40 carbon atoms, a substituted or unsubstituted germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0184] The above R 31 Inland R 37 can be connected to the above A1 to A3 rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

[0185] The above R 32 Wow R 33 , R 34 Wow R 35 and R 36 and R 37 Each of them can be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring,

[0186] In the above chemical formula 3, 'substitution' in 'substituted or unsubstituted' means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocyclic group, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocyclic ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic heterocyclic ring, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

[0187]

[0188] Here, the polycyclic ring compound represented by the above [chemical formula 3] is a boron thermally activated delayed fluorescence emitter, which enables Förster energy transfer from a triplet of a phosphorescence sensitizer to a singlet of a boron thermally activated delayed fluorescence emitter, thereby reducing the number of long-lived triplet excitons involved in device deterioration and improving the lifespan. In addition, since it has a high molar absorption coefficient, it has the advantage of improving efficiency and lifespan due to effects such as an increase in the speed of fluorescence resonance energy transfer from a phosphorescence sensitizer to a emitter and a narrowing of the emission spectrum due to a multiple resonance effect, thereby increasing color purity.

[0189] As a more preferred embodiment of the present invention, A1 to A3 in the chemical formula 3 may be the same as or different from each other, and may each independently be any one selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring.

[0190]

[0191] Hereinafter, an organic light-emitting device according to the present invention will be described with reference to the drawings.

[0192] FIG. 1 is a drawing illustrating the structure of an organic light-emitting device according to one embodiment of the present invention.

[0193] As illustrated in FIG. 1, an organic light-emitting device according to an embodiment of the present invention is an organic light-emitting device that sequentially includes an anode (20), a hole transport layer (40), a light-emitting layer (50) including a host and a dopant, an electron transport layer (60), and a cathode (80), wherein the anode is a first electrode, the cathode is a second electrode, and a hole transport layer is included between the anode and the light-emitting layer, and an electron transport layer is included between the light-emitting layer and the cathode.

[0194] In addition, the organic light-emitting device according to an embodiment of the present invention may include a hole injection layer (30) between the anode (20) and the hole transport layer (40), and an electron injection layer (70) between the electron transport layer (60) and the cathode (80).

[0195] Referring to the above drawing 1, the organic light-emitting device of the present invention and the manufacturing method thereof will be described as follows.

[0196] First, a material for an anode electrode is coated on the upper portion of a substrate (10) to form an anode (20). Here, a substrate used in a typical organic EL device is used as the substrate (10), and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofing is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used as the material for the anode electrode.

[0197] A hole injection layer (30) is formed by vacuum thermal deposition or spin coating of a hole injection layer material on top of the above anode (20) electrode. Next, a hole transport layer (40) is formed by vacuum thermal deposition or spin coating of a hole transport layer material on top of the hole injection layer (30).

[0198] The above hole injection layer material can be used without particular limitation as long as it is commonly used in the art, and for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine], NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine], HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile], etc. can be used, but the present invention is not necessarily limited thereto.

[0199] In addition, as a material of the hole transport layer, it is not particularly limited as long as it is commonly used in the art, and for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD) can be used. However, the present invention is not necessarily limited thereto.

[0200] Meanwhile, the present invention can additionally form an electron blocking layer on top of the hole transport layer. The electron blocking layer is a layer that prevents electrons injected from the electron injection layer from entering the hole transport layer through the light emitting layer, thereby improving the lifespan and efficiency of the device. The electron blocking layer can be formed at an appropriate location between the light emitting layer and the hole injection layer, and preferably, can be formed between the light emitting layer and the hole transport layer.

[0201] Next, a light-emitting layer (50) can be laminated on top of the hole transport layer (40) or electron blocking layer using a vacuum deposition method or a spin coating method.

[0202] Here, the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above.

[0203] In addition, according to a specific example of the present invention, the thickness of the light-emitting layer is preferably 50 to 2,000 Å.

[0204] The present invention can optionally form a hole blocking layer (not shown) as a thin film on top of the organic light-emitting layer (50) using a vacuum deposition method or a spin coating method.

[0205] The above hole-blocking layer prevents the lifespan and efficiency of the device from decreasing when holes pass through the light-emitting layer and flow into the cathode by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level. At this time, the hole-blocking material used is not particularly limited, but must have an electron transport ability and a higher ionization potential than the light-emitting compound, and any one selected from among BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq, and chemical formulas 1001 to 1007 may be used as the material used in the hole-blocking layer, but is not limited thereto.

[0206] BAlq BCP Bphen

[0207]

[0208] TPBI NTAZ BeBq2

[0209]

[0210] OXD-7 Liq

[0211]

[0212] Chemical Formula 1001 Chemical Formula 1002 Chemical Formula 1003

[0213]

[0214] Chemical Formula 1004 Chemical Formula 1005 Chemical Formula 1006

[0215]

[0216] Chemical Formula 1007

[0217]

[0218] Meanwhile, an electron transport layer (60) is deposited on the light-emitting layer or hole-blocking layer using a vacuum deposition method or a spin coating method.

[0219] Meanwhile, in the present invention, the electron transport layer material may be a known electron transport material that has the function of stably transporting electrons injected from an electron injection electrode (cathode). Examples of known electron transport materials include, but are not limited to, quinoline derivatives, particularly tris(8-quinolinolate)aluminum (Alq3), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq2), Compound 201, Compound 202, BCP, and oxadiazole derivatives such as PBD, BMD, and BND.

[0220]

[0221] TAZ BAlq

[0222]

[0223] Compound 201 <Compound 202> BCP

[0224]

[0225]

[0226] In addition, in the organic light-emitting device of the present invention, after forming the electron transport layer, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from a cathode, may be laminated on top of the electron transport layer, and this does not particularly limit the material.

[0227] Any material known as an electron injection layer forming material, such as CsF, NaF, LiF, Li2O, BaO, etc., can be used as the electron injection layer forming material. The deposition conditions of the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions almost identical to those for forming the hole injection layer.

[0228] The thickness of the electron injection layer may be from about 1 Å to about 100 Å, preferably from about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0229] In addition, in the present invention, the cathode may use a material having a low work function to facilitate electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or an alloy thereof, aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. may be used, or a transparent cathode using ITO or IZO may be used.

[0230] In addition, in the present invention, one or more layers selected from each of the layers may be formed by a single molecule deposition process or a solution process.

[0231] Here, the deposition process means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process means a method of forming a thin film by mixing a material used as a material for forming each layer with a solvent and using a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, or spin coating.

[0232] In addition, the organic light-emitting device of the present invention can be used in any one device selected from a flat panel display device; a flexible display device; a stretchable display device; a flat panel lighting device of a single color or white color; and a flexible lighting device of a single color or white color; a display device for a vehicle or an aircraft; and a display device for virtual or augmented reality.

[0233]

[0234] Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these embodiments are intended to illustrate the present invention more specifically, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereby.

[0235]

[0236] (Example)

[0237] Synthesis Example 1. Synthesis of [Compound 18]

[0238] Synthesis Example 1-1. Synthesis of A-1

[0239]

[0240] <a-1a> <a-1b> <a-1>

[0241] In a nitrogen-purged reactor <a-1a> 50 g, <a-1b>36.7 g, 7.9 g of tetrakis(triphenylphosphine)palladium(0), 70.7 g of potassium carbonate, 250 mL of toluene, 32 mL of water, and 150 mL of ethanol were added. After 16 hours, it was cooled to room temperature, and then ethyl acetate and water were added to separate the layers. The organic layer was concentrated under reduced pressure and recrystallized from heptane. <a-1>was obtained. (40 g, 77.8%)

[0242]

[0243] Synthesis Example 1-2. Synthesis of A-2

[0244]

[0245] <a-2a> <a-2>

[0246] In a nitrogen-purged reactor <a-2a>100 g of tosyl chloride, 90.4 g of KOH, and 1000 mL of THF were added. After stirring at room temperature for 4 hours, ethyl acetate and water were added to separate the layers. The organic layer was concentrated under reduced pressure and recrystallized from methanol. <a-2>(130.2 g, 87%) was obtained.

[0247]

[0248] Synthesis Example 1-3. Synthesis of A-3

[0249]

[0250] <a-2> <a-1> <a-3>

[0251]

[0252] In the reactor <a-2> 24 g, <a-1>Add 15.4 g of CuI, 3.36 g of K3PO4, 37.5 g of 1,2-cyclohexyldiamine, and 240 mL of toluene, stir, and reflux under nitrogen atmosphere. After the reaction is completed, the reactants are separated into layers, and the organic layer is concentrated under reduced pressure, separated and purified by column chromatography to obtain the compound. <a-3>(21.7 g, 58.3%)

[0253]

[0254] Synthesis Example 1-4. Synthesis of A-4

[0255]

[0256] <a-3> <a-4>

[0257] In a nitrogen-purged reactor <a-4>40 g of KOH, 10.8 g of EtOH, and 400 mL of ethanol were added. After stirring under reflux for 4 hours, ethyl acetate and water were added to separate the layers. The organic layer was concentrated under reduced pressure, separated and purified by column chromatography. <a-4>(25.7 g, 85.5%) was obtained.

[0258]

[0259] Synthesis Example 1-5. Synthesis of [Compound 18]

[0260]

[0261] <a-4> <a-5a>[Compound 18]

[0262] Used in the above synthesis example 1-3 <a-2>instead <a-5a>Use , <a-1>instead <a-4>[Compound 18] was obtained by the same method except that [compound 18] was used. (Yield 70.5%)

[0263] MS (MALDI-TOF): m / z 658.33 [M+]

[0264]

[0265] Synthesis Example 2. Synthesis of [Compound 26]

[0266] Synthesis Example 2-1. Synthesis of B-1

[0267]

[0268] <a-1a> <b-1a> <b-1>

[0269] Used in the above synthesis example 1-1 <a-1b>instead <b-1a>Synthesized in the same way except that <b-1>was obtained. (Yield 75.7%)

[0270]

[0271] Synthesis Example 2-2. Synthesis of B-2

[0272]

[0273] <a-2> <b-1> <b-2>

[0274] Used in the above synthesis example 1-3 <a-1>instead <b-1>Synthesized in the same way except that <b-2>was obtained. (Yield 50.3%)

[0275]

[0276] Synthesis Example 2-3. Synthesis of B-3

[0277]

[0278] <b-2> <b-3>

[0279] Used in the above synthesis example 1-4 <a-3>instead <b-2>Synthesized in the same way except that <b-3>was obtained. (Yield 75.8%)

[0280]

[0281] Synthesis Example 2-4. Synthesis of [Compound 26]

[0282]

[0283] <b-3> <b-4a>[Compound 26]

[0284] Used in the above synthesis example 1-3 <a-2>instead <b-4a>Use , <a-1>instead <b-3>Compound 26 was obtained by the same method except that it was synthesized using (yield 65.2%).

[0285] MS (MALDI-TOF): m / z 740.32 [M+]

[0286]

[0287] Synthesis Example 3. Synthesis of [Compound 31]

[0288] Synthesis Example 3-1. Synthesis of [Compound 31]

[0289]

[0290] <c-1a> <a-4>[Compound 31]

[0291] Used in the above synthesis example 1-3 <a-2>instead <c-1a>Use , <a-1>instead <a-4>[Compound 31] was obtained by the same method except that [compound 31] was used. (Yield 50.7%)

[0292] MS (MALDI-TOF): m / z 800.36 [M+]

[0293]

[0294] Synthesis Example 4. Synthesis of [Compound 46]

[0295] Synthesis Example 4-1. Synthesis of D-1

[0296]

[0297] <a-4> <d-1a> <d-1>

[0298] Used in the above synthesis example 1-3 <a-2>instead <d-1a>Use , <a-1>instead <a-4>Synthesized in the same way except that <d-1>was obtained. (Yield 70.5%)

[0299]

[0300] Synthesis Example 4-2. Synthesis of [Compound 46]

[0301]

[0302] <d-1> <d-2a>[Compound 46]

[0303] In the reactor <d-1> 23.3 g, <d-2a>Add 7.6 g, Pd2(dba)3 3.99 g, Sphos 7.16 g, STB 12.6 g, and toluene 240 mL, stir, and reflux under nitrogen. After the reaction is completed, the reactants are separated into layers, and the organic layer is concentrated under reduced pressure, separated and purified by column chromatography to obtain [Compound 46]. (13.6 g, 48.6%)

[0304] MS (MALDI-TOF): m / z 783.36 [M+]

[0305]

[0306] Synthesis Example 5. Synthesis of [Compound 47]

[0307] Synthesis Example 5-1. Synthesis of E-1

[0308]

[0309] <b-3> <d-1a> <e-1>

[0310] Used in the above synthesis example 1-3 <a-2>instead <d-1a>Use , <a-1>instead <b-3>Synthesized in the same way except that <e-1>was obtained. (Yield 65.7%)

[0311]

[0312] Synthesis Example 5-2. Synthesis of [Compound 47]

[0313]

[0314] <e-1> <d-2a>[Compound 47]

[0315] Used in the above synthesis example 4-2 <d-1>instead <e-1>Compound 47 was obtained by the same method except that it was synthesized using . (Yield 45.6%)

[0316] MS (MALDI-TOF): m / z 743.33 [M+]

[0317]

[0318] Synthesis Example 6. Synthesis of [Compound 51]

[0319] Synthesis Example 6-1. Synthesis of [Compound 51]

[0320]

[0321] <f-1a> <a-4>[Compound 51]

[0322] Used in the above synthesis example 1-3 <a-2>instead <f-1a>Use , <a-1>instead <a-4>Compound 51 was obtained by the same method except that it was synthesized using (yield 56.8%).

[0323] MS (MALDI-TOF): m / z 876.39 [M+]

[0324]

[0325] Synthesis Example 7. Synthesis of [Compound 53]

[0326] Synthesis Example 7-1. Synthesis of G-1

[0327]

[0328] <a-1a> <g-1a> <g-1>

[0329] Used in the above synthesis example 1-1 <a-1b>instead <g-1a>Synthesized in the same way except that <g-1>was obtained. (Yield 77.7%)

[0330]

[0331] Synthesis Example 7-2. Synthesis of G-2

[0332]

[0333] <g-1> <a-2> <g-2>

[0334] Used in the above synthesis example 2-2 <b-1>instead <g-1>Synthesized in the same way except that <g-2>was obtained. (Yield 63.3%)

[0335]

[0336] Synthesis Example 7-3. Synthesis of G-3

[0337]

[0338] <g-2> <g-3>

[0339] Used in the above synthesis example 1-4 <a-3>instead <g-2>Synthesized in the same way except that <g-3>was obtained. (Yield 90%)

[0340]

[0341] Synthesis Example 7-4. Synthesis of G-4

[0342]

[0343] <g-3> <d-1a> <g-4>

[0344] Used in the above synthesis example 1-3 <a-2>instead <d-1a>Use , <a-1>instead <g-3>Synthesized in the same way except that <g-4>was obtained. (Yield 63.7%)

[0345]

[0346] Synthesis Example 7-5. Synthesis of [Compound 53]

[0347]

[0348] <g-4> <d-2a>[Compound 53]

[0349] Used in the above synthesis example 4-2 <d-1>instead <g-4>[Compound 53] was obtained by the same method except that [compound 53] was used. (Yield 45.6%)

[0350] MS (MALDI-TOF): m / z 901.35 [M+]

[0351]

[0352] Synthesis Example 8. Synthesis of [Compound 54]

[0353] Synthesis Example 8-1. Synthesis of H-1

[0354]

[0355] <h-1a> <h-1b> <h-1>

[0356] Used in the above synthesis example 1-1 <a-1a>instead <h-1a>Use , <a-1b>instead <h-1b>Synthesized in the same way except that <h-1>was obtained. (Yield 40.5%)

[0357]

[0358] Synthesis Example 8-2. Synthesis of H-2

[0359]

[0360] <h-1> <a-2> <h-2>

[0361] Used in the above synthesis example 1-3 <a-1>instead <h-1>Synthesized in the same way except that <h-2>was obtained. (Yield 60.3%)

[0362]

[0363] Synthesis Example 8-3. Synthesis of H-3

[0364]

[0365] <h-2> <h-3>

[0366] Used in the above synthesis example 1-4 <a-3>instead <h-2>Synthesized in the same way except that <h-3>was obtained. (Yield 95.2%)

[0367]

[0368] Synthesis Example 8-4. Synthesis of [Compound 54]

[0369]

[0370] <h-3> <h-4a>[Compound 54]

[0371] Used in the above synthesis example 1-3 <a-2>instead <h-4a>Use , <a-1>instead <h-3>Compound 54 was obtained by the same method except that it was synthesized using . (Yield 66.7%)

[0372] MS (MALDI-TOF): m / z 770.37 [M+]

[0373]

[0374] Synthesis Example 9. Synthesis of [Compound 58]

[0375] Synthesis Example 9-1. Synthesis of I-1

[0376]

[0377] <i-1a> <a-1b> <i-1>

[0378] Used in the above synthesis example 1-1 <a-1a>instead <i-1a>Synthesized in the same way except that <i-1>was obtained. (Yield 77%)

[0379]

[0380] Synthesis Example 9-2. Synthesis of I-2

[0381]

[0382] <i-2a> <i-2>

[0383] Used in the above synthesis example 1-2 <a-2a>instead <i-2a>Synthesized in the same way except that <i-2>was obtained. (Yield 88.2%)

[0384]

[0385] Synthesis Example 9-3. Synthesis of I-3

[0386]

[0387] <i-2> <i-1> <i-3>

[0388] Used in the above synthesis example 1-3 <a-2>instead <i-2>Use , <a-1>instead <i-1>Synthesized in the same way except that <i-3>was obtained. (Yield 57.4%)

[0389]

[0390] Synthesis Example 9-4. Synthesis of I-4

[0391]

[0392] <i-3> <i-4>

[0393] Used in the above synthesis example 1-4 <a-3>instead <i-3>Synthesized in the same way except that <i-4>was obtained. (Yield 84.7%)

[0394]

[0395] Synthesis Example 9-5. Synthesis of [Compound 58]

[0396]

[0397] <i-5a> <i-4>[Compound 58]

[0398] Used in the above synthesis example 1-3 <a-2>instead <i-5a>Use , <a-1>instead <i-4>Compound 58 was obtained by the same method except that it was synthesized using . (Yield 71.2%)

[0399] MS (MALDI-TOF): m / z 833.57 [M+]

[0400]

[0401] Examples 1 to 9: Manufacturing of organic light-emitting devices

[0402] After patterning the ITO glass to have a light-emitting area of ​​2 mm × 2 mm, it was cleaned. After mounting the ITO glass in a vacuum chamber, the base pressure was 1 × 10 -6 After making it torr, HAT-CN (50 Å) is deposited as a hole injection layer on the ITO, BCFN (600 Å) is deposited as a hole transport layer, and then PBCz (50 Å) is deposited as an electron blocking layer. As a light-emitting layer, a host compound according to the present invention and the PBD below as a dopant compound are mixed at 12 wt% of the total amount of the light-emitting layer and deposited (350 Å), then mSiTrz (50 Å) is deposited as a hole-blocking layer, mSiTrz: Liq (300 Å) is deposited as an electron injection and transport layer at a ratio of 1:1, then Liq (10 Å) is deposited sequentially as an electron injection layer, and Al (1000 Å) is deposited as a cathode to manufacture an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0403] [HAT-CN] [BCFN] [PBCz]

[0404]

[0405] [PBD] [mSiTrz] [Liq]

[0406]

[0407] Comparative Examples 1 to 5

[0408] Organic light-emitting devices for comparative examples were manufactured and tested in the same manner as in the above-described examples, except that [RH-1] to [RH-5] were used instead of the compounds according to the present invention used as hosts in the device structure of the above-described examples. The luminescence characteristics of the above-described organic light-emitting devices were measured at 0.4 mA, and the measurement results are shown in Table 1 below. Here, the structures of [RH-1] to [RH-5] are as follows.

[0409] [RH-1] [RH-2] [RH-3]

[0410]

[0411] [RH-4] [RH-5]

[0412]

[0413]

[0414] As can be seen in the above [Table 1], it can be seen that a device employing a compound according to the present invention as a host compound of a light-emitting layer in an organic light-emitting device can realize a high-efficiency, long-life organic light-emitting device with excellent external quantum efficiency and lifespan characteristics at a low driving voltage compared to devices (Comparative Examples 1 to 5) employing a compound widely used in the past, which is in contrast to the characteristic structure of the compound according to the present invention.

[0415] Examples 10 to 18: Manufacturing of organic light-emitting devices

[0416] The organic light-emitting device used in Examples 1 to 9 above was manufactured and tested in the same manner, except that the heterocyclic compound according to the present invention and the compound of [ET-1] below were mixed in a weight ratio of 1:1 as a host in the light-emitting layer. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA, and the measurement results are shown in Table 3 below.

[0417] [ET-1]

[0418]

[0419] Comparative examples 6 to 10

[0420] Organic light-emitting devices for comparative examples were manufactured and tested in the same manner as in the above-described examples, except that [RH-1] to [RH-5] were used instead of the heterocyclic compound according to the present invention used as a host in the device structure of the above-described examples. The luminescence characteristics of the organic light-emitting devices were measured at 0.4 mA, and the measurement results are shown in Table 2 below.

[0421]

[0422] As shown in Table 2 above, it can be seen that the device employing the host compound of the light-emitting layer in the organic light-emitting device of the present invention can realize a high-efficiency, long-life organic light-emitting device with excellent external quantum efficiency and lifespan characteristics at a low driving voltage compared to the device (Comparative Examples 6 to 10) employing a conventionally widely used compound that has a characteristic structure of the compound according to the present invention.

[0423] Examples 19 to 22: Manufacturing of organic light-emitting devices

[0424] The organic light-emitting devices used in Examples 10 to 18 were manufactured and tested in the same manner, except that the TBD compound below was additionally mixed as a dopant compound according to the present invention at 0.5 wt% of the total amount of the light-emitting layer. The light-emitting characteristics of the organic light-emitting devices were measured at 0.4 mA, and the measurement results are shown in Table 3 below.

[0425] [TBD]

[0426]

[0427] Comparative Example 11

[0428] An organic light-emitting device for comparative example was manufactured in the same manner as the above-described example, except that [RH-1] was used instead of the compound according to the present invention as a host compound in the device structure, and the luminescence characteristics of the organic light-emitting device were measured at 0.4 mA.

[0429]

[0430] As shown in Table 3 above, it can be seen that a device employing a compound according to the present invention as a host compound of a light-emitting layer in an organic light-emitting device can realize a high-efficiency, long-life organic light-emitting device with excellent external quantum efficiency and lifespan characteristics at a low driving voltage compared to a device (Comparative Example 11) employing a conventionally widely used compound that has a characteristic structure of the compound according to the present invention.

[0431]

[0432] The novel heterocyclic compound according to the present invention, when used as a phosphorescent host material in the light-emitting layer of an organic light-emitting device, has the characteristics of lower voltage, higher efficiency, and longer lifespan compared to an organic light-emitting device according to the prior art, and thus exhibits improved characteristics when applied to an organic light-emitting device, and thus has high industrial applicability in organic light-emitting devices and related industrial fields. < / i-5a> < / i-3> < / i-1> < / i-2> < / i-2a> < / a-1b> < / i-1a> < / h-3> < / h-2> < / a-2> < / h-1> < / h-1b> < / h-1a> < / g-4> < / d-1a> < / g-3> < / g-2> < / a-2> < / g-1> < / g-1a> < / a-1a> < / f-1a> < / e-1> < / d-1a> < / b-3> < / d-1> < / d-1> < / d-1a> < / a-4> < / c-1a> < / b-3> < / b-2> < / b-1> < / a-2> < / b-1a> < / a-1a> < / a-4> < / a-3> < / a-2> < / a-1> < / a-2> < / a-2a> < / a-1a> < / a-1b> < / a-1a>

Claims

1. First electrode; a second electrode opposite to the first electrode; and An organic layer interposed between the first electrode and the second electrode; The organic layer includes a light-emitting layer including a host and a dopant; An organic light-emitting device characterized in that the host comprises at least one heterocyclic compound of the following [chemical formula 1]: [Chemical Formula 1] In the above chemical formula 1, The above R1 to R 17 are the same or different from each other, and each independently represents hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 7 to 30 carbon atoms A cycloalkyl group having a condensed ring, a cycloalkyl group having a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms, Any one selected from among an arylthio group of 30, a substituted or unsubstituted cycloalkylthio group of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group of 2 to 30 carbon atoms, a substituted or unsubstituted amine group of 0 to 40 carbon atoms, a substituted or unsubstituted silyl group of 0 to 40 carbon atoms, a substituted or unsubstituted germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, The above substituents R2 to R 17 At least one of them is a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms or a substituted or unsubstituted trypticenyl group, One of the above substituents R2 to R5 is a single bond bonding to a nitrogen atom in the lower carbazole structure of the above chemical formula 1, The above L is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, condensed with an aliphatic hydrocarbon ring. The above m is 1 or 2, and in this case, when m is 2, each L is the same or different from each other, In the above chemical formula 1, 'substitution' in 'substituted or unsubstituted' means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

2. In paragraph 1, R in the above chemical formula 1 10 Inland R 17 An organic light-emitting device characterized in that at least one of the groups is a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms or a substituted or unsubstituted trypticenyl group.

3. In paragraph 2, R in the above chemical formula 1 10 Inland R 17 An organic light-emitting device characterized in that at least one of the following structural formulae 1 to 4 is selected: [Structural formula 1] [Structural formula 2] [Structural formula 3] [Structural formula 4] Here, one carbon atom in the cycloalkane ring structure in the structural formulas 1 to 3 is a radical from which hydrogen has been removed and is bonded to a carbon atom in the benzene ring of the carbazole structure in the chemical formula 1, and one aromatic carbon atom in the trypticene ring in the structural formula 4 is a radical from which hydrogen has been removed and is bonded to a carbon atom in the benzene ring of the carbazole structure in the chemical formula 1, The hydrogen site bonded to the carbon atom in the above structural formulas 1 to 4 may be bonded to any one selected from hydrogen and deuterium.

4. In paragraph 3, The above heterocyclic compound is an organic light-emitting device characterized in that among the substituents R2 to R5 in the chemical formula 1, the substituent R4 is a single bond bonded to a nitrogen atom.

5. In paragraph 4, The above heterocyclic compound is R 10 Inland R 17 An organic light-emitting device characterized in that only one of the above structural formulae 1 to 4 is selected.

6. In paragraph 5, Above R2 to R 17 An organic light-emitting device characterized in that the substituents other than a substituted or unsubstituted cycloalkyl group or a substituted or unsubstituted trypticenyl group are the same or different from each other, and each is independently selected from hydrogen and deuterium.

7. In paragraph 6, An organic light-emitting device, characterized in that the above substituent R1 is a substituted or unsubstituted silyl group having 1 to 30 carbon atoms.

8. In paragraph 7, An organic light-emitting device characterized in that the above substituent R1 is a substituent represented by the following structural formula A: [Structural formula A] In the above structural formula A L1 to L3 are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, which is a condensed aliphatic hydrocarbon ring. The above Ar1 to Ar3 are the same or different from each other, and are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 30 carbon atoms condensed with an aliphatic hydrocarbon ring. In the above structural formula A, '*' indicates a binding site that binds to the linker L in chemical formula 1.

9. In paragraph 1, An organic light-emitting device characterized in that the compound represented by the above chemical formula 1 is one selected from the group represented by compound 1 to compound 60 below. Compound 1 Compound 2 Compound 3 Compound 4 Compound 5 Compound 6 Compound 7 Compound 8 Compound 9 Compound 10 Compound 11 Compound 12 Compound 13 Compound 14 Compound 15 Compound 16 Compound 17 Compound 18 Compound 19 Compound 20 Compound 21 Compound 22 Compound 23 Compound 24 Compound 25 Compound 26 Compound 27 Compound 28 Compound 29 Compound 30 Compound 31 Compound 32 Compound 33 Compound 34 Compound 35 Compound 36 Compound 37 Compound 38 Compound 39 Compound 40 Compound 41 Compound 42 Compound 43 Compound 44 Compound 45 Compound 46 Compound 47 Compound 48 Compound 49 Compound 50 Compound 51 Compound 52 Compound 53 Compound 54 Compound 55 Compound 56 Compound 57 Compound 58 Compound 59 Compound 60 10. In paragraph 1, An organic light-emitting device characterized in that the host in the light-emitting layer of the organic light-emitting device additionally includes at least one host compound different from the heterocyclic compound in addition to the heterocyclic compound.

11. In paragraph 10, An organic light-emitting device characterized in that, in addition to the above heterocyclic compound, a host compound different from the above heterocyclic compound is a heterocyclic compound represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, The above X1 to X3 are identical or different and are each independently CR 20 Or N, However, at least one of X1 to X3 is N, and at least two of X1 to X3 are CR. 20 In each case, CR 20 are the same or different, L 21 Inland L 23 are the same or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, and a substituted or unsubstituted arylene group having 8 to 20 carbon atoms, which is a condensed aliphatic hydrocarbon ring, The above m 21 Inland m 23 are identical or different, and are each independently an integer from 1 to 2, provided that when they are 2, each L 21 Inland L 23 are each other Same or different, The above R 20 Inland R 23 are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 7 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, a substituted or An unsubstituted cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a substituted or unsubstituted heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted Any one selected from an unsubstituted cycloalkylthio group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group having 2 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 40 carbon atoms, a substituted or unsubstituted silyl group having 0 to 40 carbon atoms, a substituted or unsubstituted germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, In the above chemical formula 2, 'substitution' in 'substituted or unsubstituted' means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

12. In paragraph 1, An organic light-emitting device characterized in that the dopant in the light-emitting layer of the organic light-emitting device uses an organometallic compound containing a transition metal.

13. In paragraph 12, An organic light-emitting device characterized in that the dopant in the light-emitting layer of the organic light-emitting device additionally includes a polycyclic compound represented by the following chemical formula 3 in addition to the organometallic compound containing the transition metal: [Chemical Formula 3] In the above [chemical formula 3], The above Y1 and Y2 are the same or different from each other, and are each independently O, S, NR 31 , CR 32 R 33 , SiR 34 R 35 and GeR 36 R 37 One of the following is selected: The above A1 to A3 are the same or different from each other, and are each independently selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 50 carbon atoms, an aromatic hydrocarbon ring having 8 to 50 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring condensed therewith, a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms, and a substituted or unsubstituted aromatic heterocycle having 5 to 50 carbon atoms, The above R 31 Inland R 37 are the same or different from each other, and each independently represents hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 7 to 30 carbon atoms A cycloalkyl group having a condensed ring, a cycloalkyl group having a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms, Any one selected from among an arylthio group of 30, a substituted or unsubstituted cycloalkylthio group of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group of 2 to 30 carbon atoms, a substituted or unsubstituted amine group of 0 to 40 carbon atoms, a substituted or unsubstituted silyl group of 0 to 40 carbon atoms, a substituted or unsubstituted germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, The above R 31 Inland R 37 can be connected to the above A1 to A3 rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, The above R 32 Wow R 33 , R 34 Wow R 35 and R 36 and R 37 Each of them can be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring, In the above chemical formula 3, 'substitution' in 'substituted or unsubstituted' means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

14. In paragraph 1, The organic light-emitting device is an organic light-emitting device used in any one of a flat panel display device; a flexible display device; a stretchable display device; a flat panel lighting device of a single color or white color; a flexible lighting device of a single color or white color; a display device for a vehicle or an aircraft; and a display device for virtual or augmented reality.

15. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, The above R1 to R 17 are the same or different from each other, and each independently represents hydrogen, deuterium, tritium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 7 to 30 carbon atoms A cycloalkyl group having a condensed ring, a cycloalkyl group having a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring having 6 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms, Any one selected from among an arylthio group of 30, a substituted or unsubstituted cycloalkylthio group of 3 to 30 carbon atoms, a substituted or unsubstituted heteroarylthio group of 2 to 30 carbon atoms, a substituted or unsubstituted amine group of 0 to 40 carbon atoms, a substituted or unsubstituted silyl group of 0 to 40 carbon atoms, a substituted or unsubstituted germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, The above substituents R2 to R 17 At least one of them is a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms or a substituted or unsubstituted trypticenyl group, One of the above substituents R2 to R5 is a single bond bonding to a nitrogen atom in the lower carbazole structure of the above chemical formula 1, The above L is any one selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and a substituted or unsubstituted arylene group having 5 to 30 carbon atoms, condensed with an aliphatic hydrocarbon ring. The above m is 1 or 2, and in this case, when m is 2, each L is the same or different from each other, In the above chemical formula 1, 'substitution' in 'substituted or unsubstituted' means deuterium, tritium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 30 carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, cycloalkyl group having 3 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 7 to 24 carbon atoms, alkylaryl group having 7 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, heteroarylalkyl group having 3 to 24 carbon atoms, alkylheteroaryl group having 3 to 24 carbon atoms, alkoxy group having 1 to 24 carbon atoms, A cycloalkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 5 to 30 carbon atoms, a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms, a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, a condensed aliphatic heterocycle, an amine group having 1 to 30 carbon atoms, a silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, an aryloxy group having 6 to 24 carbon atoms, and It means being substituted with one or more substituents selected from the group consisting of arylthionyl groups having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

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