Novel heterocyclic compound and organic light-emitting diode including same

Abstract

The present invention relates to a novel aromatic heterocyclic compound that can be used in an organic light-emitting diode and an organic light-emitting diode including same.

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]

[0010] 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.

[0011] 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.

[0012] In order to achieve the above technical tasks, the present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] [Structural Formula 1-1] [Structural Formula 1-2]

[0016]

[0017] In the above chemical formula 1, structural formula 1-1 and structural formula 1-2,

[0018] M1 and M2 are each a substituent represented by structural formula 1-1 or structural formula 1-2, except when they are simultaneously a substituent represented by structural formula 1-1, or when they are simultaneously a substituent represented by structural formula 1-2,

[0019] In the above structural formula 1-1, '*' means a binding site connected to one of the two nitrogen atoms (N) in chemical formula 1,

[0020]

[0021] *Any one of the substituents R7 in the above structural formula 1-2 is a single bond that is connected to the remaining nitrogen atom, other than the nitrogen atom to which the structural formula 1-1 is connected, among the two nitrogen atoms (N) in the chemical formula 1.

[0022] The above substituents R1 to R3, the substituent R7 excluding the single bond bonded to one of the two nitrogen atoms in the above chemical formula 1, Substituents R8 are the same or different from each other, and each independently represent 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 group having 7 to 30 carbon atoms. A cycloalkyl group having a condensed hydrocarbon 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 Any one selected from among an arylthio group having 6 to 30 carbon atoms, a substituted or 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0023] The above substituents R4 to R6 are the same or different from each other, and are each independently any one selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, but excluding those in which all of R4 to R6 are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[0024] L 11 Inland L 14 are the same or different from each other, and each independently represents 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 a substituted or unsubstituted arylene group having 8 to 20 carbon atoms, which is a condensed aliphatic hydrocarbon ring,

[0025] The above plurality of R7 and R8 may be connected to each other with adjacent substituents to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

[0026] m1 is 2, and each R1 is equal or different from each other,

[0027] m2 and m3 are each 4, and each substituent R2 and each substituent R3 in each aromatic ring are the same or different from each other,

[0028] m 11 Inland m 14 are 1 or 2 respectively, and the above m 11 In this case, each L 11 are identical or different from each other, and the above m 12 In case of 2, each L 12 are identical or different from each other, and the above m 13In this case, each L 13 are identical or different from each other, and the above m 14 In case of 2, each L 14 are identical or different from each other,

[0029] m7 and m8 are each 4, and at this time, each substituent R7 and each substituent R8 in each aromatic ring are the same or different from each other,

[0030] In the above structural formula 1-2, W is O or S,

[0031] In the above chemical formula 1, structural formula 1-1 and structural formula 1-2, '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, An alkoxy group having 1 to 24 carbon atoms, a cycloalkyl group having 7 to 30 carbon atoms and a condensed aromatic hydrocarbon ring, a cycloalkyl group having 5 to 30 carbon atoms and a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms and a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms and a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms and a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and 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, It means being substituted with one or more substituents selected from the group consisting of an aryloxy group having 6 to 24 carbon atoms and an arylthionyl group having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

[0032] 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.

[0033] Figure 1 is a schematic diagram of an organic light-emitting device according to one specific example of the present invention.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] The present invention provides a heterocyclic compound represented by the following chemical formula 1.

[0038] [Chemical Formula 1]

[0039]

[0040] [Structural Formula 1-1] [Structural Formula 1-2]

[0041]

[0042] In the above chemical formula 1, structural formula 1-1 and structural formula 1-2,

[0043] M1 and M2 are each a substituent represented by structural formula 1-1 or structural formula 1-2, except when they are simultaneously a substituent represented by structural formula 1-1, or when they are simultaneously a substituent represented by structural formula 1-2,

[0044] In the above structural formula 1-1, '*' means a binding site connected to one of the two nitrogen atoms (N) in chemical formula 1,

[0045] Among the multiple substituents R7 in the above structural formula 1-2, one of the substituents is a single bond that is connected to the remaining nitrogen atom, other than the nitrogen atom to which the structural formula 1-1 is connected, among the two nitrogen atoms (N) in the chemical formula 1.

[0046] The above substituents R1 to R3, the substituent R7 excluding the single bond bonded to one of the two nitrogen atoms in the above chemical formula 1, Substituents R8 are the same or different from each other, and each independently represent 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 group having 7 to 30 carbon atoms. A cycloalkyl group having a condensed hydrocarbon 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 Any one selected from among an arylthio group having 6 to 30 carbon atoms, a substituted or 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0047] The above substituents R4 to R6 are the same or different from each other, and are each independently any one selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, but excluding those in which all of R4 to R6 are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,

[0048] L 11 Inland L 14 are the same or different from each other, and each independently represents 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 a substituted or unsubstituted arylene group having 8 to 20 carbon atoms, which is a condensed aliphatic hydrocarbon ring,

[0049] The above plurality of R7 and R8 may be connected to each other with adjacent substituents to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

[0050] m1 is 2, and each R1 is equal or different from each other,

[0051] m2 and m3 are each 4, and each substituent R2 and each substituent R3 in each aromatic ring are the same or different from each other,

[0052] m 11 Inland m 14 are 1 or 2 respectively, and the above m 11 In this case, each L 11 are identical or different from each other, and the above m 12 In case of 2, each L 12 are identical or different from each other, and the above m 13In this case, each L 13 are identical or different from each other, and the above m 14 In case of 2, each L 14 are identical or different from each other,

[0053] m7 and m8 are each 4, and at this time, each substituent R7 and each substituent R8 in each aromatic ring are the same or different from each other,

[0054] In the above structural formula 1-2, W is O or S,

[0055] In the above chemical formula 1, structural formula 1-1 and structural formula 1-2, '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, An alkoxy group having 1 to 24 carbon atoms, a cycloalkyl group having 7 to 30 carbon atoms and a condensed aromatic hydrocarbon ring, a cycloalkyl group having 5 to 30 carbon atoms and a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms and a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms and a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms and a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and 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, It means being substituted with one or more substituents selected from the group consisting of an aryloxy group having 6 to 24 carbon atoms and an arylthionyl group having 6 to 24 carbon atoms, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

[0056] 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 the substituent is viewed as unsubstituted without considering the substituted portion. 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.

[0057] 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.

[0058] Specific examples of the above aryl group include 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, and the like, but are not limited thereto, 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.

[0059] In addition, at least one hydrogen atom of the aryl group is selected from the group consisting of a deuterium atom, a tritium 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, and an aryl group having 7 to 24 carbon atoms. It may be substituted with an alkylaryl group, 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] 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.

[0071] In the compound of the present invention, the 'cyclo' in the substituents such as cycloalkyl group, cycloalkoxy group, etc. means a substituent having a structure capable of forming a single ring or multiple rings of saturated hydrocarbon in the alkyl group or 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] The silyl group, which is a substituent used in the compound of the present invention, may include -SiH3, an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, a heteroarylsilyl group, etc., and the arylsilyl group means a silyl group in which one, two, or three hydrogens are substituted with an aryl group in -SiH3, the alkylsilyl group means a silyl group in which one, two, or three hydrogens are substituted with an alkyl group in -SiH3, and the alkylarylsilyl group means a silyl group in which at least two hydrogens are substituted with an alkyl group and an aryl group, and includes one or two alkyl groups and two or one corresponding aryl group,

[0081] An arylheteroarylsilyl group means a silyl group in which at least one hydrogen is substituted by an aryl group and a heteroaryl group in -SiH3, and which includes one or two aryl groups and two or one corresponding heteroaryl group, and a heteroarylsilyl group means a silyl group in which one or two or three hydrogens are substituted by a heteroaryl group in -SiH3, and examples of the arylsilyl group include a substituted or unsubstituted monoarylsilyl group, a substituted or unsubstituted diarylsilyl group, or a substituted or unsubstituted triarylsilyl group, and the same applies to the alkylsilyl group and the heteroarylsilyl group.

[0082] Here, each aryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylsilyl group, heteroarylsilyl group, and arylheteroarylsilyl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0083] In addition, specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, etc., and at least one hydrogen atom of the silyl group can be substituted with a substituent similar to that of the aryl group.

[0084] In addition, in the present invention, the germanium group (or germanium group, or germane group) may include -GeH3, an alkylgermanium group, an arylgermanium group, a heteroarylgermanium group, an alkylarylgermanium group, an alkylheteroarylgermanium group, an arylheteroarylgermanium group, etc., and the definitions of these are as described for the silyl group, but can be applied to each substituent as a substituent obtained by substituting a germanium atom (Ge) for a silicon atom (Si) in the silyl group.

[0085] In addition, specific examples of the germanium group include trimethylgermane, triethylgermane, triphenylgermane, trimethoxygermane, dimethoxyphenylgermane, diphenylmethylgermane, diphenylvinylgermane, methylcyclobutylgermane, dimethylfurylgermane, etc., and one or more hydrogen atoms of the germanium group can be substituted with a substituent similar to that of the aryl group.

[0086] 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.

[0087] 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.

[0088] In addition, in the present invention, the amine group may include -NH2, an alkylamine group, an arylamine group, an alkylarylamine group, an arylheteroarylamine group, a heteroarylamine group, etc., and the arylamine group means an amine in which one or two hydrogens in -NH2 are substituted with an aryl group, the alkylamine group means an amine in which one or two hydrogens in -NH2 are substituted with an alkyl group, the alkylarylamine group means an amine in which one hydrogen in -NH2 is substituted with an alkyl group and the other hydrogen in -NH2 is substituted with an aryl group, the arylheteroarylamine group means an amine in which one hydrogen in -NH2 is substituted with an aryl group and the other hydrogen in -NH2 is substituted with a heteroaryl group, and the heteroarylamine group means an amine in which one or two hydrogens in -NH2 are substituted with a heteroaryl group, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted There is a diarylamine group, and the alkylamine group and heteroarylamine group are also included.

[0089] Here, each aryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic aryl group or a polycyclic aryl group, and each heteroaryl group in the arylamine group, heteroarylamine group, and arylheteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] Meanwhile, in the present invention, the above-mentioned 'substituents R1 to R3, Excluding single bonds Among the substituents R7 and R8, the adjacent substituents can be connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, and in the case of ', this means that one hydrogen radical can be removed from each of two adjacent substituents selected from among the remaining substituents (multiple R1 substituents, multiple R2 substituents, multiple R3 substituents, multiple R4 substituents, multiple R5 substituents, multiple R6 substituents, multiple R7 substituents, multiple R8 substituents) excluding the single bond among the above R1 to R8 and connected to form an additional ring.

[0099] In the present invention, the heterocyclic compound represented by the above chemical formula 1 is characterized in that, in a condensed ring structure of '6-membered aromatic hydrocarbon ring - 5-membered ring containing a nitrogen atom - 6-membered aromatic hydrocarbon ring - 5-membered ring containing a nitrogen atom - 6-membered aromatic hydrocarbon ring', a substituent including a silicon atom, represented by structural formula 1-1, is bonded to one of the two nitrogen atoms included in the above chemical formula 1, and a carbon atom in one of the aromatic rings in the dibenzofuran (W=O) or dibenzothiophene (W=S) ring, represented by structural formula 1-2, is directly bonded to the other nitrogen atom.

[0100] As one embodiment of the present invention, the compound represented by the chemical formula 1 may contain at least one deuterium.

[0101] More specifically, at least one of the substituents R1 to R3 in the compound represented by the above chemical formula 1 may contain deuterium, or at least one of the substituents R4 to R6 may contain deuterium, or the substituent R7 (excluding the case of a single bond) or the substituent R8 may contain deuterium, and more preferably, all of the substituents R1 to R3 in the compound represented by the above chemical formula 1 may each be deuterium.

[0102] As one embodiment of the present invention, the m in structural formula 1-1 11 Inland m 14 are 1 each, and the connector L 11 Inland L 14 are identical or different from each other, and each independently may be a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0103] As one embodiment of the present invention, the connector L 11 It can be a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

[0104] As one embodiment of the present invention, the substituents R4 to R6 are the same as or different from each other, and may each independently be any one selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, and a substituted or unsubstituted aryl group having 8 to 20 carbon atoms and having an aliphatic hydrocarbon ring condensed therewith.

[0105] As one embodiment of the present invention, all of the substituents R7 to R8 in the compound represented by the above chemical formula 1 may be deuterium.

[0106] In a more preferred embodiment, the substituents R2 and R3 in the above chemical formula 1 are the same as or different from each other, and each can be independently 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.

[0107] As a more preferred embodiment, W in structural formula 1-2 of the heterocyclic compound represented by the above chemical formula 1 may be an oxygen atom (O).

[0108] 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 compound selected from 1 to 87 below, but is not limited thereto.

[0109]

[0110] 1 2 3

[0111]

[0112] 4 5 6

[0113]

[0114] 7 8 9

[0115]

[0116] 10 11 12

[0117]

[0118] 13 14 15

[0119]

[0120] 16 17 18

[0121]

[0122] 19 20 21

[0123]

[0124] 22 23 24

[0125]

[0126] 25 26 27

[0127]

[0128] 28 29 30

[0129]

[0130] 31 32 33

[0131]

[0132] 34 35 36

[0133]

[0134] 37 38 39

[0135]

[0136] 40 41 42

[0137]

[0138] 43 44 45

[0139]

[0140] 46 47 48

[0141]

[0142] 49 50 51

[0143] 52 53 54

[0144]

[0145] 55 56 57

[0146]

[0147] 58 59 60

[0148]

[0149] 61 62 63

[0150]

[0151] 64 65 66

[0152]

[0153] 67 68 69

[0154]

[0155] 70 71 72

[0156]

[0157] 73 74 75

[0158]

[0159] 76 77 78

[0160]

[0161] 79 80 81

[0162]

[0163] 82 83 84

[0164]

[0165] 85 86 87

[0166] In addition, 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.

[0167] 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.

[0168] 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 compounds.”

[0169] 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.

[0170] 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.

[0171] As an embodiment of the present invention, the host in the light-emitting layer may be used by mixing or stacking one or more different host compounds in addition to the heterocyclic compound represented by the chemical formula 1. That is, the host according to the present invention may further include one or more additional host compounds different from the one represented by the chemical formula 1, so that two or more host compounds may be mixed or stacked and used. In the case of the stacking, a host compound different from the heterocyclic compound may be stacked on or under a layer including the heterocyclic compound according to the present invention.

[0172] Here, in the case where at least one additional host compound is additionally included in addition to one compound represented by the above chemical formula 1, and two or more host compounds are mixed or laminated and used, more preferably, a compound having an electron acceptor moiety can be used as the additional host, and due to the HOMO / LUMO level of the high hole injection and electron injection barrier resulting from mixing or laminating 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, etc., it is possible to implement a high-efficiency, long-life organic light-emitting device.

[0173] 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.

[0174] More specifically, the host in the light-emitting layer of the organic light-emitting device may be used by mixing one or more organic compounds represented by the following chemical formula B in addition to the heterocyclic compound represented by the above chemical formula 1, or the organic compound represented by the following chemical formula B may be used by layering it on the upper or lower part of a layer including the heterocyclic compound represented by the above chemical formula 1.

[0175] [Chemical Formula B]

[0176]

[0177] In the above [chemical formula B],

[0178] X1 to X3 are identical or different and are each independently N or CR. 24 However, at least one of the above X1 to X3 is N, and at least two of the above X1 to X3 are CR 24 In each case, CR 24 are the same or different,

[0179] 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,

[0180] 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,

[0181] R 21 Inland R 24are 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 carbon atoms, 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 germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0182] In the above chemical formula B, '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 30 carbon atoms, alkynyl group having 2 to 30 carbon atoms, cycloalkyl group having 3 to 30 carbon atoms, heteroalkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, arylalkyl group having 7 to 30 carbon atoms, alkylaryl group having 7 to 30 carbon atoms, heteroaryl group having 2 to 30 carbon atoms, heteroarylalkyl group having 3 to 30 carbon atoms, alkylheteroaryl group having 3 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, A cycloalkyl group having a condensed aromatic hydrocarbon ring of 30, a cycloalkyl group having a condensed aromatic heterocycle of 5 to 30 carbon atoms, a heterocycloalkyl group having a condensed aromatic hydrocarbon ring of 6 to 30 carbon atoms, an aryl group having a condensed aliphatic hydrocarbon ring of 7 to 30 carbon atoms, a heteroaryl group having a condensed aliphatic hydrocarbon ring of 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic heterocycle of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic heterocycle of 5 to 30 carbon atoms, 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 30 carbon atoms, and a carbon number It means being substituted with one or more substituents selected from the group consisting of 6 to 30 arylthionyl groups, and one or more hydrogens in the substituents can be replaced with deuterium or tritium.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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. are used, but are not limited thereto, and more preferably, PtOEP, Ir(Bt)2acac, Ir(MDQ)2acac, Ir(piq)3, Ir(piq)2acac, Ir(pq)2acac, etc. used as red phosphorescent dopants can be used, but are not limited thereto.

[0187] In addition, the light-emitting layer may additionally 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 be used by mixing or laminating one or more types of dopant compounds containing boron, which are different from the organic metal compound containing the transition metal.

[0188] More specifically, the dopant in the light-emitting layer of the organic light-emitting device may be used by mixing one or more polycyclic ring compounds represented by the following [Chemical Formula 2] in addition to the organometallic compound containing the transition metal, or the polycyclic ring compound represented by the above [Chemical Formula 2] may be used by being layered on the upper or lower portion of the layer containing the organometallic compound.

[0189] [Chemical Formula 2]

[0190]

[0191] In the above [chemical formula 2],

[0192] Y1 and Y2 are the same or different and are independently O, S, NR 11 , CR 12 R 13 , SiR 14 R 15 and GeR 16 R 17 One of the following is selected:

[0193] 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.

[0194] R 11 Inland 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 carbon atoms, 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 germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group,

[0195] The above R 11 Inland R 17 can be connected to the above A1 to A3 rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

[0196] The above R 12 Wow R 13 , R 14 Wow R 15 and R 16 and R 17 Each of them can be linked to each other to form an additional alicyclic or aromatic monocyclic or polycyclic ring,

[0197]

[0198] *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 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.

[0199] Here, the polycyclic ring compound represented by the above [chemical formula 2] 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.

[0200] In a more preferred embodiment of the present invention, A1 to A3 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.

[0201] Hereinafter, an organic light-emitting device according to the present invention will be described with reference to the drawings.

[0202] FIG. 1 is a drawing illustrating the structure of an organic light-emitting device according to one embodiment of the present invention.

[0203] 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.

[0204] 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).

[0205] 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.

[0206] 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.

[0207] 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).

[0208] 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.

[0209] 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.

[0210] 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.

[0211] 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.

[0212] Here, the light-emitting layer may be composed of a host and a dopant, and the materials constituting them are as described above.

[0213] 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.

[0214] 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.

[0215] 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.

[0216] BAlq BCP Bphen

[0217]

[0218] TPBI NTAZ BeBq2

[0219]

[0220] OXD-7 Liq

[0221]

[0222] Chemical Formula 1001 Chemical Formula 1002 Chemical Formula 1003

[0223]

[0224] Chemical Formula 1004 Chemical Formula 1005 Chemical Formula 1006

[0225]

[0226] Chemical Formula 1007

[0227]

[0228] 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.

[0229] 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.

[0230]

[0231] TAZ BAlq

[0232]

[0233] Compound 201 <Compound 202> BCP

[0234]

[0235]

[0236] 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.

[0237] 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.

[0238] 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.

[0239] 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.

[0240] 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.

[0241] 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.

[0242] 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 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.

[0243] 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.

[0244] (Example)

[0245] Synthesis Example 1. Synthesis of [Compound 2]

[0246] Synthesis Example 1-1. Synthesis of A-1

[0247]

[0248] <a-1a> <a-1b> <a-1>

[0249] In a round bottom flask <a-1a> 30 g, <a-1b>76.4 g of copper iodide, 1.7 g of potassium phosphate, 76.2 g of potassium phosphate, 41.1 g of 1,2-cyclohexanediamine (cis:trans = 50:50) and 750 mL of 1,4-dioxane were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, filtered through Celite, and the filtrate was concentrated under reduced pressure. After concentration, it was recrystallized using tetrahydrofuran and heptane. <a-1>(67.5 g, 62%)

[0250] Synthesis Example 1-2. Synthesis of [Compound 2]

[0251]

[0252] <a-1> <a-2a>[Compound 2]

[0253] In a round bottom flask <a-1> 10 g, <a-2a>5.4 g of trisdibenzylideneacetone dipalladium, 0.5 g of sodium tert-butoxide, 4.9 g of tri-tert-butylphosphine, and 100 mL of toluene were added and refluxed for 3 hours. After the reaction was completed, the reaction solution was cooled to room temperature, methanol was added dropwise, and the mixture was stirred. The reaction solution was filtered and washed with water and methanol. The obtained solid was recrystallized using tetrahydrofuran and acetone to obtain [Compound 2]. (5.6 g, 41.4%)

[0254] MS (MALDI-TOF): m / z 756.26 [M + ]

[0255] Synthesis Example 2. Synthesis of [Compound 11]

[0256] Synthesis Example 2-1. Synthesis of B-1

[0257]

[0258] <a-1a> <b-1a> <b-1>

[0259] Used in the above synthesis example 1-2 <a-1b>instead <b-1a>Synthesized in the same way except that <b-1>was obtained. (Yield 63.7%)

[0260] Synthesis Example 2-2. Synthesis of [Compound 11]

[0261]

[0262] <b-1> <b-2a>[Compound 11]

[0263] Used in the above synthesis example 1-2 <a-1>instead <b-1>Use , <a-2a>instead <b-2a>[Compound 11] was obtained by the same method except that [compound 11] was used. (Yield 32.7%)

[0264] MS (MALDI-TOF): m / z 756.26 [M + ]

[0265] Synthesis Example 3. Synthesis of [Compound 15]

[0266] Synthesis Example 3-1. Synthesis of C-1

[0267]

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

[0269] In a round bottom flask <c-1a> 150 g, <c-1b>60.8 g of triphenylphosphine tetrakispalladium, 17.3 g of triphenylphosphine tetrakispalladium, 137.9 g of potassium carbonate, 1050 mL of toluene, 260 mL of ethanol and 500 mL of water were added and refluxed for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the layers were separated with ethyl acetate and water, and the organic layer was concentrated under reduced pressure and purified using column chromatography. <c-1>(79.8 g, 63.7%)

[0270] Synthesis Example 3-2. Synthesis of C-2

[0271]

[0272] <c-1> <c-2a> <c-2>

[0273] In a round bottom flask <c-1> 79.8 g, <c-2a>64.5 g of triphenylphosphine tetrakispalladium, 11 g of triphenylphosphine tetrakispalladium, 87.5 g of potassium carbonate, 560 mL of toluene, 450 mL of dioxane, and 315 mL of water were added and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the layers were separated with ethyl acetate and water, and the organic layer was treated as anhydrous and concentrated under reduced pressure. After that, the residue was purified by column chromatography. <c-2>(64 g, 68.4%) was obtained.

[0274] Synthesis Example 3-3. Synthesis of C-3

[0275]

[0276] <c-2> <c-3>

[0277] In a round bottom flask under nitrogen atmosphere <c-2>Add 64 g of dichloromethane and 640 mL of dichloromethane and cool to below 0°C. Then, slowly add 162.4 g of boron tribromide dropwise, and when the addition is complete, raise the reaction solution to room temperature and stir for 8 hours. When the reaction is complete, pour the reaction solution into water and stir for 30 minutes, then separate the layers into dichloromethane and water, and then anhydrous the organic layer, concentrate under reduced pressure, and dry in vacuum. <c-3>(56.5 g, 92.5%) was obtained.

[0278] Synthesis Example 3-4. Synthesis of C-4

[0279]

[0280] <c-3> <c-4>

[0281] In a round bottom flask <c-3>56.5 g of sodium hydroxide, 82.9 g of potassium carbonate, and 570 mL of N,N-dimethylacetamide were added and refluxed for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature and poured into water to precipitate crystals. After stirring for 1 hour, it was filtered. The filtered solid was washed with methanol and the obtained solid was recrystallized with dichloromethane and methanol. <c-4>(40 g, 76.3%) was obtained.

[0282] Synthesis Example 3-5. Synthesis of [Compound 15]

[0283]

[0284] <a-1> <c-4>[Compound 15]

[0285] In a round bottom flask <a-1> 12 g, <c-4>6.4 g, 19.9 g of cesium carbonate, and 100 mL of N,N-dimethylacetamide were added and refluxed for 24 hours. After the reaction was completed, the reaction solution was cooled to room temperature, poured into water, stirred for 1 hour, filtered, and washed with methanol. The obtained solid was purified by column chromatography to obtain [Compound 15]. (7.5 g, 44.3%)

[0286] MS (MALDI-TOF): m / z 832.29 [M + ]

[0287] Synthesis Example 4. Synthesis of [Compound 20]

[0288] Synthesis Example 4-1. Synthesis of D-1

[0289]

[0290] <d-1a> <c-1b> <d-1>

[0291] Used in the above synthesis example 3-1 <c-1a>Instead <d-1a>Synthesized in the same way except that <d-1>was obtained. (Yield 62.5%)

[0292] Synthesis Example 4-2. Synthesis of D-2

[0293]

[0294] <d-1> <d-2a> <d-2>

[0295] Used in the above synthesis example 3-2 <c-1>instead <d-1>Use , <c-2a>instead <d-2a>Synthesized in the same way except that <d-2>was obtained. (Yield 68.1%)

[0296] Synthesis Example 4-3. Synthesis of D-3

[0297]

[0298] <d-2> <d-3>

[0299] Used in the above synthesis example 3-3 <c-2>instead <d-2>Synthesized in the same way except that <d-3>was obtained. (Yield 90.2%)

[0300] Synthesis Example 4-4. Synthesis of D-4

[0301]

[0302] <d-3> <d-4>

[0303] Used in the above synthesis example 3-4 <c-3>instead <d-3>Synthesized in the same way except that <d-4>was obtained. (Yield 75.7%)

[0304] Synthesis Example 4-5. Synthesis of D-5

[0305]

[0306] <a-1a> <d-4> <d-5>

[0307] Used in the above synthesis example 3-5 <a-1>instead <a-1a>Use , <c-4>instead <d-4>Synthesized in the same way except that <d-5>was obtained. (Yield 72.3%)

[0308] Synthesis Example 4-6. Synthesis of [Compound 20]

[0309]

[0310] <d-5> <a-1b>[Compound 20]

[0311] Used in the above synthesis example 1-2 <a-1>instead <d-5>Use , <a-2a>instead <a-1b>[Compound 20] was obtained by the same method except that [compound 20] was used. (Yield 43.3%)

[0312] MS (MALDI-TOF): m / z 832.29 [M + ]

[0313] Synthesis Example 5. Synthesis of [Compound 28]

[0314] Synthesis Example 5-1. Synthesis of E-1

[0315]

[0316] <e-1a> <e-1>

[0317] In a round bottom flask <e-1a>40 g and 600 mL of N,N-dimethylformamide were added and cooled to 0°C. 35.1 g of N-bromosuccinimide was dissolved in 175 mL of N,N-dimethylformamide and slowly added dropwise. After stirring at room temperature for 6 hours, when the reaction was complete, the reaction solution was poured into heptane, stirred for 1 hour, and filtered. <e-1>(47.8 g, 90.2%) was obtained.

[0318] Synthesis Example 5-2. <e-2>Synthesis of

[0319]

[0320] <e-1> <e-2>

[0321] In a round bottom flask <e-1>47.8 g of bispinacolatodiboron, 49 g of diphenylphosphinopalladium dichloride, 14.1 g of potassium acetate, and 480 mL of 1,4-dioxane were added and refluxed for 7 hours. After the reaction was completed, the reaction solution was cooled to room temperature and filtered through Celite, the filtrate was concentrated, crystallized with heptane, and filtered. The obtained solid was dissolved in toluene, filtered through silica gel, the filtrate was concentrated, crystallized with heptane, and filtered. <e-2>(47.7 g, 87.2%) was obtained.

[0322] Synthesis Example 5-3. <e-3>Synthesis of

[0323]

[0324] <e-2> <e-3a> <e-3>

[0325] Used in the above synthesis example 3-2 <c-1>instead <e-3a>Use , <c-2a>instead <e-2>Synthesized in the same way except that <e-3>was obtained. (Yield 58.8%)

[0326] Synthesis Example 5-4. <e-4>Synthesis of

[0327]

[0328] <e-3> <e-4>

[0329] In a round bottom flask <e-3>27.6 g of triphenylphosphine, 59.6 g of triphenylphosphine, and 280 mL of 1,2-dichlorobenzene were added and refluxed for 15 hours. After the reaction was completed, the reaction solution was cooled to room temperature, concentrated under reduced pressure, and purified by column chromatography. <e-4>was obtained. (16.2 g, yield 64.5%)

[0330] Synthesis Example 5-5. <e-5>Synthesis of

[0331]

[0332] <e-4> <a-1b> <e-5>

[0333] Used in the above synthesis example 1-1 <a-1a>instead <e-4>Synthesized in the same way except that <e-5>was obtained. (Yield 64.1%)

[0334] Synthesis Example 5-6. Synthesis of [Compound 28]

[0335]

[0336] <e-5> <e-6a>[Compound 28]

[0337] Used in the above synthesis example 1-2 <a-1>instead <e-5>Use , <a-2a>instead <e-6a>Compound 28 was obtained by the same method except that it was synthesized using (yield 38.6%).

[0338] MS (MALDI-TOF): m / z 832.29 [M + ]

[0339] Synthesis Example 6. Synthesis of [Compound 37]

[0340] Synthesis Example 6-1. Synthesis of F-1

[0341]

[0342] <f-1a> <f-1>

[0343] In a round bottom flask <f-1a>60 g of ethyl acetate and 480 mL of tetrahydrofuran were added and cooled to -78°C. 185.8 mL of N-butyllithium (1.6 M) was slowly added dropwise and stirred for 2 hours while maintaining the temperature. 54.3 g of trimethyl borate was slowly added dropwise and stirred at room temperature for 12 hours. When the reaction was complete, the reaction solution was poured into water and stirred for 30 minutes. After separating the layers with ethyl acetate and water, the organic layer was anhydrous, concentrated under reduced pressure, and dried in vacuo. <f-1>was obtained. (43.2 g, yield 84.2%)

[0344] Synthesis Example 6-2. <f-2>Synthesis of

[0345]

[0346] <a-1a> <a-2a> <f-2>

[0347] Used in the above synthesis example 1-1 <a-1b>instead <a-2a>Synthesized in the same way except that <f-2>was obtained. (Yield 68.2%)

[0348] Synthesis Example 6-3. <f-3>Synthesis of

[0349]

[0350] <f-2> <a-1b> <f-3>

[0351] Used in the above synthesis example 1-2 <a-1>instead <f-2>Use , <a-2a>instead <a-1b>Synthesized in the same way except that <f-3>was obtained. (Yield 77.2%)

[0352] Synthesis Example 6-4. <f-4>Synthesis of

[0353]

[0354] <f-3> <f-4>

[0355] In a round bottom flask <f-3>18.6 g, 190 mL of dichloromethane was added and cooled to 0°C. 5.9 g of N-bromosuccinimide was dissolved in 60 mL of N,N-dimethylformamide and slowly added dropwise, stirring for 8 hours. When the reaction was complete, the reaction solution was warmed to room temperature, concentrated under reduced pressure, and purified by column chromatography. <f-4>was obtained. (15 g, yield 73.2%)

[0356] Synthesis Example 6-5. Synthesis of [Compound 37]

[0357]

[0358] <f-4> <f-1>[Compound 37]

[0359] Used in the above synthesis example 3-2 <c-1>instead <f-4>Use , <c-2a>instead <f-1>Compound 37 was obtained by the same method except that it was synthesized using . (Yield 46.2%)

[0360] MS (MALDI-TOF): m / z 917.38 [M + ]

[0361] Synthesis Example 7. Synthesis of [Compound 45]

[0362] Synthesis Example 7-1. Synthesis of G-1

[0363]

[0364] <g-1a> <c-1b> <g-1>

[0365] Used in the above synthesis example 3-1 <c-1a>instead <g-1a>Synthesized in the same way except that <g-1>was obtained. (Yield 44.9%)

[0366] Synthesis Example 7-2. Synthesis of [Compound 45]

[0367]

[0368] <a-1> <g-1>[Compound 45]

[0369] Used in the above synthesis example 1-2 <a-2a>instead <g-1>Compound 45 was obtained by the same method except that it was synthesized using . (Yield 44.3%)

[0370] MS (MALDI-TOF): m / z 848.27 [M + ]

[0371] Synthesis Example 8. Synthesis of [Compound 58]

[0372] Synthesis Example 8-1. Synthesis of H-1

[0373]

[0374] <h-1a> <h-2a> <h-1>

[0375] Used in the above synthesis example 3-1 <c-1a>instead <h-2a>Use , <c-1b>instead <h-1a>Synthesized in the same way except that <h-1>was obtained. (Yield 61.1%)

[0376] Synthesis Example 8-2. Synthesis of H-2

[0377]

[0378] <h-1> <h-2>

[0379] Used in the above synthesis example 5-1 <e-1a>instead <h-1>Synthesized in the same way except that <h-2>was obtained. (Yield 83.2%)

[0380] Synthesis Example 8-3. Synthesis of H-3

[0381]

[0382] <h-2> <h-3>

[0383] Used in the above synthesis example 5-2 <e-1>instead <h-2>Synthesized in the same way except that <h-3>was obtained. (Yield 79.6%)

[0384] Synthesis Example 8-4. Synthesis of H-4

[0385]

[0386] <h-3> <e-3a> <h-4>

[0387] Used in the above synthesis example 3-2 <c-1>instead <h-3>Use , <c-2a>instead <e-3a>Synthesized in the same way except that <h-4>was obtained. (Yield 51.3%)

[0388] Synthesis Example 8-5. <h-5>Synthesis of

[0389]

[0390] <h-4> <h-5>

[0391] Used in the above synthesis example 5-4 <e-3>instead <h-4>Synthesized in the same way except that <h-5>was obtained. (Yield 63.7%)

[0392] Synthesis Example 8-6. <h-6>Synthesis of

[0393]

[0394] <h-5> <a-1b> <h-6>

[0395] Used in the above synthesis example 1-1 <a-1a>instead <h-5>Synthesized in the same way except that <h-6>was obtained. (Yield 61%)

[0396] Synthesis Example 8-7. Synthesis of [Compound 58]

[0397]

[0398] <h-6> <a-2a>[Compound 58]

[0399] Used in the above synthesis example 1-2 <a-1>instead <h-6>Compound 58 was obtained by the same method except that it was synthesized using . (Yield 39.2%)

[0400] MS (MALDI-TOF): m / z 938.28 [M + ]

[0401] Synthesis Example 9. Synthesis of [Compound 64]

[0402] Synthesis Example 9-1. Synthesis of I-1

[0403]

[0404] <i-1a> <i-1>

[0405] Used in the above synthesis example 5-2 <e-1>instead <i-1a>Synthesized in the same way except that <i-1>was obtained. (Yield 83.2%)

[0406] Synthesis Example 9-2. Synthesis of I-2

[0407]

[0408] <i-1> <i-2a> <i-2>

[0409] Used in the above synthesis example 5-3 <e-2>instead <i-1>Use , <e-3a>instead <i-2a>Synthesized in the same way except that <i-2>was obtained. (Yield 60.8%)

[0410] Synthesis Example 9-3. Synthesis of I-3

[0411]

[0412] <i-2> <i-3>

[0413] Used in the above synthesis example 5-4 <e-3>instead <i-2>Synthesized in the same way except that <i-3>was obtained. (Yield 68.3%)

[0414] Synthesis Example 9-4. Synthesis of I-4

[0415]

[0416] <i-3> <a-1b> <i-4>

[0417] Used in the above synthesis example 1-1 <a-1a>instead <i-3>Synthesized in the same way except that <i-4>was obtained. (Yield 65.3%)

[0418] Synthesis Example 9-5. Synthesis of [Compound 64]

[0419]

[0420] <i-4> <i-5a>[Compound 64]

[0421] Used in the above synthesis example 1-2 <a-1>instead <i-4>Use , <a-2a>instead <i-5a>Compound 64 was obtained by the same method except that it was synthesized using . (Yield 42.3%)

[0422] MS (MALDI-TOF): m / z 766.32 [M + ]

[0423] Synthesis Example 10. Synthesis of [Compound 70]

[0424] Synthesis Example 10-1. Synthesis of J-1

[0425]

[0426] <j-1a> <j-1b> <j-1>

[0427] In a round bottom flask <j-1b>50 g, 500 mL of THF was added under nitrogen atmosphere and cooled to -78°C, then 121.51 mL of 1.6 M n-butyllithium was slowly added dropwise. After stirring for 1 hour, <j-1b>Diluted in 308 mL of THF, slowly added and stirred at -78°C for 1 hour and at room temperature for 12 hours. After completion of the reaction, extracted with water, and the organic layer was concentrated under reduced pressure and separated by column chromatography. <j-1>(43.7 g, 70%) was obtained.

[0428] Synthesis Example 10-2. Synthesis of J-2

[0429]

[0430] <i-3> <j-1> <j-2>

[0431] Used in the above synthesis example 1-1 <a-1a>instead <i-3>Use , <a-1b>instead <j-1>Synthesized in the same way except that <j-2>(Yield 65%)

[0432] Synthesis Example 10-3. Synthesis of [Compound 70]

[0433]

[0434] <j-2> <i-5a>[Compound 70]

[0435] Used in the above synthesis example 1-2 <a-1>instead <j-2>Use , <a-2a>instead <i-5a>[Compound 70] was obtained by the same method except that [compound 70] was used. (Yield 68.3%)

[0436] MS (MALDI-TOF): m / z 704.31 [M + ]

[0437] Synthesis Example 11. Synthesis of [Compound 71]

[0438] Synthesis Example 11-1. Synthesis of K-1

[0439]

[0440] <i-3> <a-2a> <k-1>

[0441] Used in the above synthesis example 1-1 <a-1a>instead <i-3>Use , <a-1b>instead <a-2a>Synthesized in the same way except that <k-1>was obtained. (Yield 65.2%)

[0442] Synthesis Example 11-2. Synthesis of K-2

[0443]

[0444] <k-2a> <j-1b> <k-2>

[0445] Used in the above synthesis example 10-1 <j-1a>instead <k-2a>Synthesized in the same way except that <k-2>was obtained. (Yield 67%)

[0446] Synthesis Example 11-3. Synthesis of [Compound 71]

[0447]

[0448] <k-1> <k-2>[Compound 71]

[0449] Used in the above synthesis example 1-2 <a-1>instead <k-1>Use , <a-2a>instead <k-2>Compound 71 was obtained by the same method except that [compound 71] was used. (Yield 67.4%)

[0450] MS (MALDI-TOF): m / z 642.29 [M + ]

[0451] Synthesis Example 12. Synthesis of [Compound 72]

[0452] Synthesis Example 12-1. Synthesis of L-1

[0453]

[0454] <l-1a> <l-1b> <l-1>

[0455] Used in the above synthesis example 10-1 <j-1a>instead <l-1a>Use , <j-1b>instead <l-1b>Synthesized in the same way except that <l-1>(Yield 60%)

[0456] Synthesis Example 12-2. Synthesis of L-2

[0457]

[0458] <l-1> <j-1b> <l-2>

[0459] Used in the above synthesis example 10-1 <j-1a>instead <l-1>Synthesized in the same way except that <l-2>was obtained. (Yield 65%)

[0460] Synthesis Example 12-3. Synthesis of L-3

[0461]

[0462] <a-1a> <l-2> <l-3>

[0463] Used in the above synthesis example 1-1 <a-1b>instead <l-2>Synthesized in the same way except that <l-3>was obtained. (Yield 66%)

[0464] Synthesis Example 12-4. Synthesis of [Compound 72]

[0465]

[0466] <l-3> <e-6a>[Compound 72]

[0467] Used in the above synthesis example 1-2 <a-1>instead <l-3>Use , <a-2a>instead <e-6a>[Compound 72] was synthesized using the same method except that [compound 72] was used. (Yield 71%)

[0468] MS (MALDI-TOF): m / z 866.37 [M + ]

[0469]

[0470] Examples 1 to 12: Manufacturing of organic light-emitting devices

[0471] 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, the first host compound and the second 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 at a 1:1 ratio as an electron injection and transport layer, and then Liq (10 Å) is deposited sequentially as an electron injection layer, and Al (1000 Å) is deposited as a cathode, thereby manufacturing an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0472] [HAT-CN] [BCFN] [PBCz]

[0473]

[0474] [PBD] [mSiTrz] [Liq]

[0475]

[0476] [ET-1]

[0477]

[0478]

[0479] Comparative Examples 1 to 6

[0480] 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-6] 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-6] are as follows.

[0481] [RH-1] [RH-2] [RH-3]

[0482]

[0483] [RH-4] [RH-5] [RH-6]

[0484]

[0485] Classification Host (1:1) Driving voltage (V) External quantum efficiency (EQE, %) Lifespan (T95, hr) Emission color (color) Example 1 Compound 2 ET-13.9 16.7 182 Blue Example 2 Compound 11 ET-13.9 17.0 140 Blue Example 3 Compound 15 ET-14.2 16.5 144 Blue Example 4 Compound 20 ET-14.0 17.2 168 Blue Example 5 Compound 28 ET-14.1 17.0 187 Blue Example 6 Compound 37 ET-14.0 16.4 169 Blue Example 7 Compound 45 ET-14.1 16.1 158 Blue Example 8 Compound 58ET-14.216.5131 Blue Example 9 Compound 64ET-14.016.9205 Blue Example 10 Compound 70ET-13.916.6173 Blue Example 11 Compound 71ET-14.016.8180 Blue Example 12 Compound 72ET-14.117.0186 Blue Comparative Example 1RH-1ET-15.111.765 Blue Comparative Example 2RH-2ET-14.58.184 Blue Comparative Example 3RH-3ET-14.67.773 Blue Comparative Example 4RH-4ET-14.57.570 Blue Comparative Example 5RH-5ET-14.77.672 Blue Comparative Example 6RH-6ET-15.18.174 Blue

[0486] As shown in the above [Table 1], 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 6) employing a compound widely used in the past, which is in contrast to the characteristic structure of the compound according to the present invention.

[0487]

[0488] Examples 13 to 24: Manufacturing of organic light-emitting devices

[0489] The organic light-emitting devices used in Examples 1 to 12 above 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 2 below. Here, the structure of [TBD] is as follows.

[0490] [TBD]

[0491]

[0492]

[0493] Comparative examples 7 to 12

[0494] An organic light-emitting device for comparative example was manufactured in the same manner as the above-described example, except that [RH-1] to [RH-6] were used instead of the compound according to the present invention as a host compound in the device structure of the above-described example, and the luminescence characteristics of the organic light-emitting device were measured at 0.4 mA.

[0495] Classification Host (1:1) Driving voltage (V) External quantum efficiency (EQE, %) Lifespan (T95, hr) Emission color (color) Example 13 Compound 2 ET-14.117.1201 Blue Example 14 Compound 11 ET-14.117.2159 Blue Example 15 Compound 15 ET-14.516.8171 Blue Example 16 Compound 20 ET-14.317.6188 Blue Example 17 Compound 28 ET-14.417.2208 Blue Example 18 Compound 37 ET-14.216.8184 Blue Example 19 Compound 45 ET-14.516.6173 Blue Example 20 Compound 58ET-14.617.0163 Blue Example 21 Compound 64ET-14.417.0224 Blue Example 22 Compound 70ET-14.117.0192 Blue Example 23 Compound 71ET-14.217.2199 Blue Example 24 Compound 72ET-14.317.4205 Blue Comparative Example 7RH-1ET-15.312.184 Blue Comparative Example 8RH-2ET-14.78.5103 Blue Comparative Example 9RH-3ET-14.88.192 Blue Comparative Example 10RH-4ET-14.77.989 Blue Comparative Example 11RH-5ET-14.98.091 Blue Comparative Example 12RH-6ET-15.38.593 Blue

[0496] As shown in the above [Table 2], 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 7 to 12) employing a compound widely used in the past, which is in contrast to the characteristic structure of the compound according to the present invention.

[0497]

[0498] Examples 25 to 28: Manufacturing of organic light-emitting devices

[0499] The organic light-emitting devices used in Examples 1 to 12 above were manufactured and tested in the same manner, except that the heterocyclic compound according to the present invention was used alone as a host in 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.

[0500]

[0501] Comparative Example 13

[0502] An organic light-emitting device for comparative example was manufactured and tested in the same manner as in the above-described embodiment, except that RH-2 was used instead of the heterocyclic compound according to the present invention used as a host in the device structure, and the luminescence characteristics of the organic light-emitting device were measured at 0.4 mA, and the measurement results are shown in Table 3 below.

[0503] Classification Host driving voltage (V) External quantum efficiency (EQE) Lifespan (T95, hr) Emission color (color) Example 25 Compound 25.6 7.8 9 1 Blue Example 26 Compound 205.8 9.1 8 5 Blue Example 27 Compound 285.8 8.3 8 2 Blue Example 28 Compound 645.9 8.2 10 1 Blue Comparative Example 13RH-26.5 5.6 4 8 Blue

[0504] As shown in the above [Table 3], 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 (device according to Comparative Example 13) employing a conventionally widely used compound that has a characteristic structure of the compound according to the present invention.

[0505] When the heterocyclic compound according to the present invention is used as a phosphorescent host material in the light-emitting layer of an organic light-emitting device, it exhibits characteristics of lower voltage, higher efficiency, and longer lifespan compared to organic light-emitting devices according to the prior art, and therefore has high industrial applicability in industrial fields such as the organic light-emitting device and display fields. < / l-3> < / l-2> < / a-1a> < / j-1b> < / l-1> < / l-1b> < / l-1a> < / k-1> < / j-1b> < / k-2a> < / a-2a> < / i-3> < / j-2> < / j-1> < / i-3> < / j-1b> < / j-1a> < / i-4> < / a-1b> < / i-3> < / i-2> < / i-2a> < / i-1> < / i-1a> < / h-6> < / a-1b> < / h-5> < / h-4> < / e-3a> < / h-3> < / h-2> < / h-1> < / h-2a> < / h-1a> < / a-1> < / c-1b> < / g-1a> < / f-4> < / f-3> < / a-1b> < / f-2> < / a-2a> < / a-1a> < / f-1a> < / e-5> < / a-1b> < / e-4> < / e-3> < / e-3a> < / e-2> < / e-1> < / e-1a> < / d-5> < / d-4> < / a-1a> < / d-3> < / d-2> < / d-2a> < / d-1> < / c-1b> < / d-1a> < / a-1> < / a-1> < / c-3> < / c-2> < / c-1> < / c-2a> < / c-1> < / c-1a> < / c-1b> < / c-1a> < / b-1> < / b-1a> < / a-1a> < / a-1> < / a-1> < / a-1a> < / a-1b> < / a-1a>

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical Formula 1] [Structural Formula 1-1] [Structural Formula 1-2] In the above chemical formula 1, structural formula 1-1 and structural formula 1-2, M1 and M2 are each a substituent represented by structural formula 1-1 or structural formula 1-2, except when they are both substituents represented by structural formula 1-1, or when they are both substituents represented by structural formula 1-2, In the above structural formula 1-1, '*' means a binding site connected to one of the two nitrogen atoms (N) in chemical formula 1, Among the multiple substituents R7 in the above structural formula 1-2, one of the substituents is a single bond that is connected to the remaining nitrogen atom, other than the nitrogen atom to which the above structural formula 1-1 is connected, among the two nitrogen atoms (N) in the chemical formula 1. The above substituents R1 to R3, the substituent R7 excluding the single bond bonded to one of the two nitrogen atoms in the above chemical formula 1, Substituents R8 are the same or different from each other, and each independently represent 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 group having 7 to 30 carbon atoms. A cycloalkyl group having a condensed hydrocarbon 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 Any one selected from among an arylthio group having 6 to 30 carbon atoms, a substituted or 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 germanium group having 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, The above substituents R4 to R6 are the same or different from each other, and are each independently any one selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted aryl group having 8 to 30 carbon atoms, a condensed aliphatic hydrocarbon ring, and a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, but excluding those in which all of R4 to R6 are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, L 11 Inland L 14 are the same or different from each other, and each independently represents 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 a substituted or unsubstituted arylene group having 8 to 20 carbon atoms, which is a condensed aliphatic hydrocarbon ring, The above plurality of R7 and R8 may be connected to each other with adjacent substituents to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, m1 is 2, and each R1 is equal or different from each other, m2 and m3 are each 4, and each substituent R2 and each substituent R3 in each aromatic ring are the same or different from each other, m 11 Inland m 14 are 1 or 2 respectively, and the above m 11 In this case, each L 11 are identical or different from each other, and the above m 12 In case of 2, each L 12 are identical or different from each other, and the above m 13 In this case, each L 13 are identical or different from each other, and the above m 14 In case of 2, each L 14 are identical or different from each other, m7 and m8 are each 4, and at this time, each substituent R7 and each substituent R8 in each aromatic ring are the same or different from each other, In the above structural formula 1-2, W is O or S, In the above chemical formula 1, structural formula 1-1 and structural formula 1-2, '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, An alkoxy group having 1 to 24 carbon atoms, a cycloalkyl group having 7 to 30 carbon atoms and a condensed aromatic hydrocarbon ring, a cycloalkyl group having 5 to 30 carbon atoms and a condensed aromatic heterocycle, a heterocycloalkyl group having 6 to 30 carbon atoms and a condensed aromatic hydrocarbon ring, an aryl group having 7 to 30 carbon atoms and a condensed aliphatic hydrocarbon ring, a heteroaryl group having 5 to 30 carbon atoms and a condensed aliphatic hydrocarbon ring, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a condensed aliphatic heterocycle, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms and 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, It means being substituted with one or more substituents selected from the group consisting of an aryloxy group having 6 to 24 carbon atoms and an arylthionyl group 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, A heterocyclic compound characterized in that the compound represented by the above chemical formula 1 contains at least one deuterium.

3. In paragraph 2, A heterocyclic compound characterized in that at least one substituent among the above R1 to R3 contains deuterium.

4. In paragraph 3, A heterocyclic compound characterized in that each of the above R1 to R3 is deuterium.

5. In paragraph 1, The above m 11 Inland m 14 are 1 each, Above L 11 Inland L 14 A heterocyclic compound characterized in that each of the following groups is the same or different and each group independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.

6. In paragraph 1, A heterocyclic compound characterized in that the above R4 to R6 are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms, and an aryl group having 8 to 20 carbon atoms, a substituted or unsubstituted aliphatic hydrocarbon ring condensed therewith.

7. In paragraph 1, A heterocyclic compound characterized in that both of the above substituents R7 and R8 are each deuterium.

8. In paragraph 1, A heterocyclic compound characterized in that W in the above structural formula 1-2 is O.

9. In paragraph 1, The compound represented by the above chemical formula 1 is a heterocyclic compound characterized in that it is one selected from the group represented by 1 to 87 below: 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 10. 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 described in any one of claims 1 to 9.

11. In paragraph 10, An organic light-emitting device characterized in that the host in the light-emitting layer of the organic light-emitting device is used by mixing or layering at least one host compound different from the heterocyclic compound.

12. In paragraph 10, 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 is used by mixing at least one polycyclic ring compound represented by the following [Chemical Formula 2] in addition to the organometallic compound containing the transition metal, or the polycyclic ring compound represented by the above [Chemical Formula 2] is used by being laminated on the upper or lower part of the layer containing the organometallic compound: [Chemical Formula 2] In the above [chemical formula 2], Y1 and Y2 are the same or different and are independently O, S, NR 11 , CR 12 R 13 , SiR 14 R 15 and GeR 16 R 17 One of the following is selected: 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. R 11 Inland 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 carbon atoms, 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 germanium group of 0 to 40 carbon atoms, a nitro group, a cyano group, and a halogen group, The above R 11 Inland R 17 can be connected to the above A1 to A3 rings to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, The above R 12 Wow R 13 , R 14 Wow R 15 and R 16 and R 17 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 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 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.

14. In paragraph 13, An organic light-emitting device characterized in that the above A1 to A3 are the same or different from each other, and are each independently selected from among a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon ring having 8 to 50 carbon atoms, which is a condensed aliphatic hydrocarbon ring.

15. In paragraph 10, 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 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.

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