WO2023249370A1

WO2023249370A1 - Novel heterocyclic compound and organic light-emitting diode including same

Info

Publication number: WO2023249370A1
Application number: PCT/KR2023/008525
Authority: WO
Inventors: 곽상우; 김명준; 홍승오; 최호정; 정재경; 신봉기
Original assignee: 에스에프씨 주식회사
Priority date: 2022-06-23
Filing date: 2023-06-20
Publication date: 2023-12-28
Also published as: KR20240001047A

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 compounds and organic light-emitting devices containing them

The present invention relates to a novel compound that can be used in organic light-emitting devices, and more specifically, to a novel compound that can be used as a host material for the light-emitting layer in an organic light-emitting device, through which device characteristics of low voltage, high efficiency, and long lifespan can be realized. It relates to a heterocyclic compound and an organic light-emitting device containing the same.

Organic light emitting diode (OLED) is a display that uses the self-luminescence phenomenon, and has advantages such as a large viewing angle, being lightweight and compact compared to liquid crystal displays, and fast response speed, so it is full-color. ) Application to displays or lighting is expected.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows. These organic light-emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

Materials used as organic layers in organic light-emitting devices can be classified into light-emitting 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 light-emitting materials can be classified into high-molecular-type and low-molecular-type types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. .

On the other hand, when only one substance is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and problems arise such as color purity being reduced or the efficiency of the device being reduced due to the emission attenuation effect. Therefore, color purity is increased and energy is reduced. A host-dopant system can be used as a light-emitting material to increase light-emitting efficiency through transition.

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, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

Among these light-emitting layers, heterocyclic compounds containing heteroatoms such as nitrogen and oxygen have recently been studied as host compounds for organic light-emitting devices using phosphorescence, and related prior art is published in Patent Publication No. 10-2020-0139834 ( 2020.12.14), an organic light-emitting device containing an aromatic heterocyclic compound with a polycyclic ring structure as a phosphorescent host was developed. It is listed.

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-described prior art, novel compounds that are still applicable to organic light-emitting devices and have device characteristics of low voltage operation, high efficiency, and long lifespan. The need for development of a compound and an organic light-emitting device containing the same continues to be required.

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 for the light-emitting layer in an organic light-emitting device.

In addition, the second technical problem to be achieved by the present invention is to provide a low-voltage, high-efficiency, and long-life organic light emitting diode (OLED) containing the organic compound as a host material in the organic light emitting device.

In order to achieve the above technical problems, the present invention provides an aromatic heterocyclic compound represented by the following [Chemical Formula A].

[Formula A] [Structural Formula Q]

In the above formula A and structural formula Q,

Ar ₁ to Ar ₃ are the same or different from each other, and each independently represents 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, or a substituted or unsubstituted carbon number. Among the aromatic hydrocarbon rings in which 8 to 50 aliphatic hydrocarbon rings are condensed, the substituted or unsubstituted aromatic heterocycles in which 2 to 50 carbon atoms are condensed, and the aromatic heterocycles in which substituted or unsubstituted aliphatic hydrocarbon rings are condensed in 5 to 50 carbon atoms. Any one selected, wherein at least one of Ar ₁ to Ar ₃ has the structural formula Q;

When Ar ₁ or Ar ₃ has the structural formula Q, the two adjacent substituents among R ₁ to R ₄ of the structural formula Q are single bonds bonding to the nitrogen atom (N) and Ar ₂ in the formula A, respectively,

When Ar ₂ has the structural formula Q, the three adjacent substituents among R ₁ to R ₄ of the structural formula Q are single bonds bonding to the nitrogen atom (N), Ar ₁ and Ar ₃ in the formula A, respectively,

The R ₁ to R ₁₀ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group. Alkynyl group with 2 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group with 5 to 30 carbon atoms, substituted or An 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 heteroaryl group having 7 to 30 carbon atoms, A cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed, a heterocycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring is condensed in 6 to 30 carbon atoms, A substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 1 to 30 carbon atoms. alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Select from a heteroarylthio group, 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, or a halogen group. Any one that can be,

At least one of R ₁ to R ₁₀ of the structural formula Q is any one of the following structural formulas H and I,

[Structural Formula H] [Structural Formula I]

In structural formula H and structural formula I,

L ₁ and L ₂ are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and a substituted or unsubstituted group. It is any one selected from arylene groups in which an aliphatic hydrocarbon ring having 8 to 50 carbon atoms is condensed,

The m is an integer from 0 to 4, but when m is 2 or more, each linking group L1 is the same or different from each other,

The n is an integer from 0 to 4, but when n is 2 or more, each linking group L2 is the same or different from each other,

In _the structural formula _I _, _X ₁ to

When X ₁ to X ₆ includes a plurality of CR ₁₃ , each CR ₁₃ is the same or different,

R ₁₁ to R ₁₃ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group. Alkynyl group with 2 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group with 5 to 30 carbon atoms, substituted or An 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 heteroaryl group having 7 to 30 carbon atoms, A cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed, a heterocycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring is condensed in 6 to 30 carbon atoms, A substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 1 to 30 carbon atoms. alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Select from a heteroarylthio group, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, or a halogen group. It's one of those things,

In _the structural formula _I , when _X ₁ to ,

In the structural formula Q, R ₁ to R ₁₀ may each be connected to adjacent groups to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

In the formula A, structural formula Q, structural formula H and structural formula I, 'substituted' in 'substituted or unsubstituted' means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 30 carbon atoms, and 1 to 30 carbon atoms. halogenated alkyl group, alkenyl group with 2 to 30 carbon atoms, alkynyl group with 2 to 30 carbon atoms, cycloalkyl group with 3 to 30 carbon atoms, heteroalkyl group with 1 to 30 carbon atoms, aryl group with 6 to 30 carbon atoms, and 7 to 30 carbon atoms. Arylalkyl group, alkylaryl group with 7 to 30 carbon atoms, heteroaryl group with 2 to 30 carbon atoms, heteroarylalkyl group with 3 to 30 carbon atoms, alkylheteroaryl group with 3 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, 7 carbon atoms A cycloalkyl group with a condensed aromatic hydrocarbon ring having 30 to 30 carbon atoms, a cycloalkyl group with a fused aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group with a fused aromatic hydrocarbon ring having 6 to 30 carbon atoms, a heterocycloalkyl group with 7 to 30 carbon atoms, Aryl group with a condensed aliphatic hydrocarbon ring, a heteroaryl group with a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group with a condensed aliphatic heteroring having 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group with 5 to 30 carbon atoms condensed with aliphatic heteroring, amine group with 1 to 30 carbon atoms, silyl group with 1 to 30 carbon atoms, germanium group with 1 to 30 carbon atoms, aryloxy group with 6 to 30 carbon atoms and 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.

When the heterocyclic compound represented by Formula A according to the present invention is used as a phosphorescent host material for the light-emitting layer in an organic light-emitting device, the organic light-emitting device can achieve lower voltage, higher efficiency, and longer lifespan characteristics than the organic light-emitting device according to the prior art. A light emitting device can be provided.

1 is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail. In each drawing of the present invention, the size or dimensions of the structures are enlarged or reduced from the actual size for clarity of the present invention, and known structures are omitted to reveal the characteristic structure, so it is not limited to the drawing. .

In addition, the size and thickness of each component shown in the drawings are arbitrarily shown for convenience of explanation, so the present invention is not necessarily limited to what is shown, and the thickness is enlarged to clearly express various layers and regions in the drawings. indicated. And in the drawings, for convenience of explanation, the thicknesses of some layers and regions are exaggerated. When a part of a layer, membrane, region, plate, etc. is said to be “on” another part, this includes not only being “directly on” the other part, but also cases where there is another part in between.

In addition, throughout the specification, when a part is said to "include" a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary. In addition, throughout the specification, “on” means located above or below the object part, and does not necessarily mean located above the direction of gravity.

The present invention provides a heterocyclic compound represented by the following [Chemical Formula A].

[Formula A] [Structural Formula Q]

In the above formula A and structural formula Q,

When Ar ₁ or Ar ₃ has structural formula Q, R ₁ of structural formula QAmong R ₄ to R 4 , the two substituents adjacent to each other are single bonds bonding to the nitrogen atom (N) and Ar ₂ in Formula A, respectively,

[Structural Formula H] [Structural Formula I]

In structural formula H and structural formula I,

The m is an integer from 0 to 4, but when m is 2 or more, each linking group L ₁ is the same or different from each other,

The n is an integer from 0 to 4, but when n is 2 or more, each linking group L ₂ is the same or different from each other,

In _the structural formula _I _, _X ₁ to

In _the structural formula _I , when _X ₁ to ,

Meanwhile, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" in the present invention, the The range of the carbon number of the alkyl group having 1 to 30 carbon atoms and the aryl group having 5 to 50 carbon atoms means the total number of carbon atoms constituting the alkyl portion or aryl portion when the substituent is regarded as unsubstituted without considering the substituted portion, respectively. will be. For example, a phenyl group substituted with a butyl group at the para position should be viewed as corresponding to an aryl group with 6 carbon atoms substituted with a butyl group with 4 carbon atoms.

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 removal of one hydrogen. When the aryl group has a substituent, it can be fused with neighboring substituents to further form a ring. Additionally, the aryl group may include an organic radical obtained by removing one hydrogen from an arene ring formed by condensing two arene rings.

Specific examples of the aryl group include phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, Aromatic radical groups such as pyrenyl group, indenyl group, fluorenyl group, tetrahydronaphthyl group, perylenyl group, chrysenyl group, naphthacenyl group, fluoranthenyl group, triphenylenyl group, etc. are included, but are limited to these. Rather, it is an organic radical formed by the removal of one hydrogen in an arene ring formed by condensing two arene rings, such as an arene ring in which a fluorene ring and a phenylene ring are condensed, or an arene ring in which a fluorene ring and a phenanthrene ring are condensed. It can also be included.

In addition, one or more hydrogen atoms of the aryl group may be a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R'' ), R' and R" are independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, carbon number 1 to 24 alkyl group, halogenated alkyl group with 1 to 24 carbon atoms, alkenyl group with 2 to 24 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 1 to 24 carbon atoms, aryl group with 6 to 24 carbon atoms, aryl with 7 to 24 carbon atoms It may be substituted with an alkyl group, an alkylaryl group with 7 to 24 carbon atoms, a heteroaryl group with 2 to 24 carbon atoms, a heteroarylalkyl group with 3 to 24 carbon atoms, or an alkylheteroaryl group with 3 to 24 carbon atoms.

In the present invention, the aromatic hydrocarbon ring refers to an aromatic ring made up of carbon and hydrogen, and the aliphatic hydrocarbon ring refers to a hydrocarbon ring made up of carbon and hydrogen but does not belong to the aromatic hydrocarbon ring. In this case, the aliphatic ring refers to a hydrocarbon ring made up of carbon and hydrogen. The hydrocarbon ring is preferably a hydrocarbon ring in which at least 30% or more of the carbon atoms forming the ring are bonded through an sp ³ orbital structure and contain 0 to 3 double bonds and/or triple bonds in the ring. , more preferably, at least 50% or more of the carbon atoms forming the ring are bonded by sp ³ orbitals, and may be a hydrocarbon ring containing 0 to 2 double bonds and/or triple bonds in the ring.

In addition, in the present invention, the aryl group in which the aliphatic hydrocarbon ring is condensed consists of two carbon atoms adjacent to each other in the aliphatic hydrocarbon ring and two carbon atoms excluding the carbon atom that becomes an organic radical by removing the hydrogen of one of the carbon atoms forming the ring in the aryl group. It refers to a cyclic substituent in which two adjacent carbon atoms are condensed together to share one double bond and has overall non-aromaticity. Specific examples include tetrahydronaphthyl group, tetrahydrobenzocycloheptene, and tetrahydrophene. Examples include, but are not limited to, a nantrene group, a tetrahydroanthracenyl group, and an octahydrotriphenylene group.

The heteroaryl group, which is a substituent used in the compound of the present invention, contains 1, 2, or 3 heteroatoms selected from N, O, P, Si, S, Ge, Se, and Te in the aromatic ring, and the remaining ring atom is carbon. It refers to an aryl group of an aromatic system with 2 to 24 rings, and the rings can be fused to form a ring. And one or more hydrogen atoms of the heteroaryl group may be replaced with the same substituent as that of the aryl group.

Specific examples of the heteroaryl group include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, and pyrimidinyl group. , triazinyl group, triazolyl group, acridinyl group, carbolinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinolinyl group, indolyl group, carbamine Zolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzofuranyl group, benzothiophenyl group, benzoselenophene group, dibenzothiophenyl group, dibenzofuranyl group, dibenzosele Nophen group, phenanthrolinyl group, thiazolinyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenoxazinyl group, phenothiazinyl group, azadibenzofuranyl group, azadi Examples include, but are not limited to, benzothiophenyl group, azadibenzoselenophene group, and indolocarbazole group.

In addition, in the present invention, the aromatic heterocycle means that one or more aromatic carbons in the aromatic hydrocarbon ring are substituted with a hetero atom, and the aromatic hetero ring preferably has 1 to 3 aromatic carbons in the aromatic hydrocarbon ring consisting of N, O, P, It may be substituted with one or more heteroatoms selected from Si, S, Ge, Se, and Te.

In addition, heteroaryl groups in which aliphatic hydrocarbon rings are condensed A substituent having a structure in which a heteroaryl group is substituted for an aryl group in the aryl group in which the aliphatic hydrocarbon ring is condensed, specific examples include tetrahydroindole group, tetrahydrobenzofuranyl group, tetrahydrobenzothiophene group, tetrahydrocarbazole group, Examples include, but are not limited to, tetrahydrodibenzofuranyl group, tetrahydrobenzothiophene group, tetrahydroquinoline group, and tetrahydroquinoxaline group.

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 of an aromatic hydrocarbon ring and two adjacent carbon atoms of an aliphatic hydrocarbon ring are shared. , Examples include tetrahydronaphthalene and dihydroindene rings, in which two adjacent carbon atoms of a benzene ring and a cyclohexane ring are shared and condensed.

In addition, in the present invention, the 'condensed ring in which an aromatic heterocycle and an aliphatic hydrocarbon ring are condensed' is a condensed ring in which two adjacent carbon atoms of an aromatic heterocycle and two adjacent carbon atoms of an aliphatic hydrocarbon ring are shared. It means, and an example is a hexahydrodibenzofuran ring in which two adjacent carbon atoms in each ring of a benzofuran ring and a cyclohexane ring are shared and condensed.

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 straight-chain and branched structure, and specific examples thereof include methyl, ethyl, propyl, isopropyl, isobutyl, and sec. -butyl, tert-butyl, pentyl, iso-amyl, hexyl, etc., and one or more hydrogen atoms of the alkyl group may be replaced with the same substituent as that of the aryl group.

'Cyclo' in the cycloalkyl group, cycloalkoxy group, etc., which are substituents used in the compound of the present invention, refers to a substituent with a structure capable of forming a single ring or multiple rings of a saturated hydrocarbon in an alkyl or alkoxy group, for example, the specific substituent of the cycloalkyl group. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, methylcyclohexyl, ethylcyclopentyl, ethylcyclohexyl, adamantyl, dicyclopentadienyl, decahydronaphthyl, norbornyl, bornyl, Isobornyl, etc. may be included, but are not limited thereto, and one or more hydrogen atoms of the cycloalkyl group may be replaced by the same substituent as that of the aryl group, and this may also be applied to cycloalkoxy.

In addition, in the present invention, the heterocycloalkyl group means that at least one carbon in the ring of the substituent forming the cycloalkyl structure is substituted with a hetero atom, preferably, 1 to 3 carbons are N, O, P, S, It may be substituted with one or more heteroatoms selected from Si, Ge, Se, and Te.

In addition, the cycloalkyl group in which the aromatic hydrocarbon ring or aromatic hetero ring is condensed contains two carbon atoms adjacent to each other in the aromatic hydrocarbon ring or aromatic hetero ring; and an organic radical by removal of hydrogen from one of the carbon atoms forming the ring in the cycloalkyl group. means a cyclic substituent that is condensed with each other and shares one double bond, and exhibits overall non-aromaticity; a specific example is tetrahydronaphthyl. , tetrahydrophenanthrene group, tetrahydroquinoline group, tetrahydroquinoxaline group, cyclopentabenzofuran, etc., but is not limited thereto.

In addition, the heterocycloalkyl group in which the aromatic hydrocarbon ring is condensed means that one or more carbon atoms in the cycloalkyl ring in the cycloalkyl group in which the aromatic hydrocarbon ring is condensed are substituted with a hetero atom, and preferably 1 to 1 in the cycloalkyl ring. It is a substituent in which three carbons are substituted with one or more heteroatoms selected from N, O, P, S, Si, Ge, Se, and Te. Specific examples include hexahydrodibenzofuranyl group, hexahydrocarbazole group, and hexahydrodi. Benzothiophene groups, dihydrobenzodioxine groups, etc. may be mentioned, but are not limited thereto, and exhibit non-aromaticity overall.

In addition, an aryl group or heteroaryl group in which an aliphatic heterocycle is condensed 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 in which the aliphatic hydrocarbon ring is condensed. Specific examples include chroman group, dihydropyranopyridine group, thiochroman group, and dihydrobenzodioxin. group, dihydrothiopyranopyridine group, dihydropyranopyrimidine group, etc., but is not limited thereto, and exhibits non-aromaticity overall.

In addition, the aliphatic heterocycle means that at least one carbon in the aliphatic hydrocarbon ring is substituted with a hetero atom, and the aliphatic heterocycle preferably has 1 to 3 carbon atoms in the aliphatic hydrocarbon ring at least one hetero atom selected from N, O, or S. It can be replaced with an atom.

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 end of an alkyl group or cycloalkyl group, and specific examples thereof include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, and iso. -Amyloxy, hexyloxy, cyclobutyloxy, cyclopentyloxy, adamantaneoxy, dicyclopentaneoxy, bornyloxy, isobornyloxy, etc., but are not limited thereto, and one or more of the alkoxy groups above The hydrogen atom can be substituted with the same substituent as in the case of the aryl group above.

Specific examples of the arylalkyl group as a substituent used in the compound of the present invention include phenylmethyl (benzyl), phenylethyl, phenylpropyl, naphthylmethyl naphthylethyl, etc., but are not limited thereto, and one of the arylalkyl groups above is not limited thereto. The above hydrogen atoms can be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkylaryl group as a substituent used in the compound of the present invention include tolyl, xylenyl, dimethylnaphthyl, t-butylphenyl, t-butylnaphthyl, and t-butylphenanthryl, but are limited thereto. This does not mean that at least one hydrogen atom of the alkylaryl group can be replaced with the same substituent as that of the aryl group.

Specific examples of the silyl group as a substituent used in the compound of the present invention include trimethylsilyl group, triethylsilyl group, triphenylsilyl group, trimethoxysilyl group, dimethoxyphenylsilyl group, diphenylmethylsilyl group, and diphenylvinyl group. Silyl group, naphthalenyldiphenylsilyl group, dibenzothiophenyldiphenylsilyl group, dibenzofuranyldiphenylsilyl group, bisdibenzothiophenylphenylsilyl group, bisdibenzofuranylphenylsilyl group, methylcyclobutylsilyl group. , dimethylfurylsilyl group, fluorenyldiphenylsilyl group, etc., but are not limited thereto, and one or more hydrogen atoms of the silyl group may be replaced with the same substituent as in the case of the aryl group.

In addition, in the present invention, an alkenyl group refers to an alkyl substituent containing one carbon-carbon double bond made up of two carbon atoms, and an alkynyl group means one made up of two carbon atoms. It refers to an alkyl substituent containing a carbon-carbon triple bond.

In addition, the alkylene group used in the present invention is an organic radical derived by removing two hydrogens in an alkane molecule, which is a straight-chain or branched saturated hydrocarbon. Specific examples of the alkylene group include methylene group. , ethylene group, propylene group, isopropylene group, isobutylene group, sec-butylene group, tert-butylene group, pentylene group, iso-amylene group, hexylene group, etc., but is not limited thereto. One or more hydrogen atoms in the alkylene group may be replaced with the same substituent as in the case of the aryl group.

In addition, in the present invention, diarylamino group refers to an amine group in which two identical or different aryl groups described above are bonded to a nitrogen atom, and diheteroarylamino group in the present invention refers to an amine group in which two identical or different heteroaryl groups are bonded to a nitrogen atom. The aryl (heteroaryl) amino group refers to an amine group in which the aryl group and the heteroaryl group are each bonded to a nitrogen atom.

Meanwhile, as a more preferable example of 'substitution' in 'substituted or unsubstituted' in the formula A, it is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 12 carbon atoms, and 1 to 12 carbon atoms. halogenated alkyl group, alkenyl group with 2 to 12 carbon atoms, alkynyl group with 2 to 12 carbon atoms, cycloalkyl group with 3 to 12 carbon atoms, heteroalkyl group with 1 to 12 carbon atoms, aryl group with 6 to 18 carbon atoms, and 7 to 20 carbon atoms. Arylalkyl group, alkylaryl group with 7 to 20 carbon atoms, heteroaryl group with 2 to 18 carbon atoms, heteroarylalkyl group with 3 to 18 carbon atoms, alkylheteroaryl group with 3 to 18 carbon atoms, aromatic hydrocarbon ring with 9 to 20 carbon atoms Condensed cycloalkyl group, a cycloalkyl group in which an aromatic heteroring having 7 to 20 carbon atoms is condensed, a heterocycloalkyl group in which an aromatic hydrocarbon ring in which 9 to 20 carbon atoms is condensed, an aryl group in which an aliphatic hydrocarbon ring in which 9 to 20 carbon atoms is condensed , a heteroaryl group in which an aliphatic hydrocarbon ring having 7 to 20 carbon atoms is condensed, An alkoxy group with 1 to 12 carbon atoms, an amine group with 1 to 18 carbon atoms, a silyl group with 1 to 18 carbon atoms, a germanium group with 1 to 18 carbon atoms, an aryloxy group with 6 to 18 carbon atoms, and an arylthionyl group with 6 to 18 carbon atoms. It may be substituted with one or more substituents selected from the group consisting of, and one or more hydrogens in each substituent may be replaced with deuterium.

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

In addition, in the present invention, as a more preferred example of the cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed, it is a cycloalkyl group in which a substituted or unsubstituted aromatic heteroring having 7 to 20 carbon atoms is condensed. It may be a cycloalkyl group.

In addition, in the present invention, the substituted or unsubstituted carbon number is 6 As a more preferable example of a heterocycloalkyl group in which a 30 to 30 aromatic hydrocarbon ring is condensed, it may be a substituted or unsubstituted heterocycloalkyl group in which a 9 to 20 carbon atom aromatic hydrocarbon ring is condensed.

In addition, in the present invention, as a more preferred example of the aryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring having 8 to 30 carbon atoms is condensed, it is an aryl group in which a substituted or unsubstituted aliphatic hydrocarbon ring having 9 to 20 carbon atoms is condensed. It may be an aryl group.

In addition, in the present invention, as a more preferred example of the heteroaryl group in which the substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 30 carbon atoms is condensed, it is a substituted or unsubstituted heteroaryl group having 7 to 20 carbon atoms in which the aliphatic hydrocarbon ring is condensed. It may be a heteroaryl group.

In addition, in the present invention, as a more preferable example of an aryl group in which a substituted or unsubstituted aliphatic heterocycle having 6 to 30 carbon atoms is condensed, it is an aryl group in which a substituted or unsubstituted aliphatic heteroring having 7 to 20 carbon atoms is condensed. It may be an aryl group.

In addition, in the present invention, as a more preferred example of a heteroaryl group in which a substituted or unsubstituted aliphatic heterocycle having 5 to 30 carbon atoms is condensed, it is a group in which a substituted or unsubstituted aliphatic heteroring having 6 to 20 carbon atoms is condensed. It may be a heteroaryl group.

Meanwhile, in the present invention, 'R ₁ to R ₁₀ may be connected to adjacent groups to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,' in the case of 'R ₁ to R ₁₀ This means that a ring can be additionally formed by removing one hydrogen radical from each of the two selected substituents and connecting them.

In the present invention, the heterocyclic compound represented by the formula A has an Ar ₁ to Ar ₃ ring centered on a nitrogen atom bonded to the nitrogen atom, and the Ar ₂ ring is connected to the Ar ₁ ring and the Ar ₃ ring, and the Ar At least one of ₁ to Ar ₃ is a phenanthrene ring represented by structural formula Q, and at least one of R ₁ to R ₁₀ in the phenanthrene ring is a substituent selected from structural formula H and structural formula I. .

[Formula A] [Structural Formula Q]

As an example of the present invention, the remaining rings other than structural formula Q among Ar ₁ to Ar ₃ of Formula A may be a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 12 carbon atoms.

As an example of the present invention, the compound represented by Formula A may contain at least one deuterium.

In one embodiment of the present invention, Ar ¹ or Ar ³ may have structural formula Q.

As an example of the present invention, Ar ² may have the structural formula Q.

As an embodiment of the present invention, only one of R ₁ to R ₁₀ of the structural formula Q may be a substituent represented by the structural formula H, and preferably, only one of R ₅ to R ₈ may be a substituent represented by the structural formula H. You can.

As an embodiment of the present invention, only one of R ₁ to R ₁₀ of the structural formula Q may be a substituent represented by the structural formula I, and preferably, only one of R ₅ to R ₈ is a substituent represented by the structural formula I. You can.

In one embodiment of _the present invention, the ring containing X ₁ to It can be any one ring.

As an embodiment of the present invention, in the structural formula H and structural formula I, the linking groups L ₁ and L ₂ are the same as or different from each other, and each independently may be a single bond or an arylene group having 6 to 14 carbon atoms.

Additionally, as a specific example of the heterocyclic compound represented by Formula A of the present invention, it may be any one compound selected from 1 to 486 below, but is not limited thereto.

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

88 89 90

91 92 93

94 95 96

97 98 99

100 101 102

103 104 105

106 107 108

109 110 111

112 113 114

115 116 117

118 119 120

121 122 123

124 125 126

127 128 129

130 131 132

133 134 135

136 137 138

139 140 141

142 143 144

145 146 147

148 149 150

151 152 153

154 155 156

157 158 159

160 161 162

163 164 165

166 167 168

169 170 171

172 173 174

175 176 177

178 179 180

181 182 183

184 185 186

187 188 189

190 191 192

193 194 195

196 197 198

199 200 201

202 203 204

205 206 207

208 209 210

211 212 213

214 215 216

217 218 219

220 221 222

223 224 225

226 227 228

229 230 231

232 233 234

235 236 237

238 239 240

241 242 243

244 245 246

247 248 249

250 251 252

253 254 255

256 257 258

259 260 261

262 263 264

265 266 267

268 269 270

271 272 273

274 275 276

277 278 279

280 281 282

283 284 285

286 287 288

289 290 291

292 293 294

295 296 297

298 299 300

301 302 303

304 305 306

307 308 309

310 311 312

313 314 315

316 317 318

319 320 321

322 323 324

325 326 327

328 329 330

331 332 333

334 335 336

337 338 339

340 341 342

343 344 345

346 347 348

349 350 351

352 353 354

355 356 357

358 359 360

361 362 363

364 365 366

367 368 369

370 371 372

373 374 375

376 377 378

379 380 381

382 383 384

385 386 387

388 389 390

391 392 393

394 395 396

397 398 399

400 401 402

403 404 405

406 407 408

409 410 411

412 413 414

415 416 417

418 419 420

421 422 423

424 425 426

427 428 429

430 431 432

433 434 435

436 437 438

439 440 441

442 443 444

445 446 447

448 449 450

451 452 453

454 455 456

457 458 459

460 461 462

463 464 465

466 467 468

469 470 471

472 473 474

475 476 477

478 479 480

481 482 483

484 485 486

Additionally, the present invention can provide a heterocyclic compound represented by the following formula (A').

[Formula A'] [Structural Formula Q]

In the above formula A' and structural formula Q,

The R ₁ to R ₁₀ are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group. Alkynyl group with 2 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group with 5 to 30 carbon atoms, substituted or An 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 heteroaryl group having 7 to 30 carbon atoms, A cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed, a heterocycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring is condensed in 6 to 30 carbon atoms, A substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 1 to 30 carbon atoms. alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Select from a heteroarylthio group, a substituted or unsubstituted amine group having 0 to 60 carbon atoms, a substituted or unsubstituted silyl group having 0 to 60 carbon atoms, a germanium group having 0 to 60 carbon atoms, a nitro group, a cyano group, or a halogen group. Any one that can be,

At least one of R ₁ to R ₁₀ of the structural formula Q is not hydrogen or deuterium,

In the formula A' and structural formula Q, 'substituted' in 'substituted or unsubstituted' means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 30 carbon atoms, halogenated alkyl group with 1 to 30 carbon atoms, Alkenyl group with 2 to 30 carbon atoms, alkynyl group with 2 to 30 carbon atoms, cycloalkyl group with 3 to 30 carbon atoms, heteroalkyl group with 1 to 30 carbon atoms, aryl group with 6 to 30 carbon atoms, arylalkyl group with 7 to 30 carbon atoms, 7 carbon atoms Alkylaryl group with 30 to 30 carbon atoms, heteroaryl group with 2 to 30 carbon atoms, heteroarylalkyl group with 3 to 30 carbon atoms, alkylheteroaryl group with 3 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, aromatic with 7 to 30 carbon atoms Cycloalkyl group with a condensed hydrocarbon ring, a cycloalkyl group with a condensed aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group with a condensed aromatic hydrocarbon ring with 6 to 30 carbon atoms, and a condensed aliphatic hydrocarbon ring with 7 to 30 carbon atoms. aryl group, a heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having a condensed aliphatic heterocycle having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 5 to 30 carbon atoms , a heteroaryl group in which an aliphatic hetero ring is condensed, an amine group having 1 to 40 carbon atoms, a silyl group having 1 to 40 carbon atoms, a germanium group having 1 to 40 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms. It means being substituted with one or more substituents selected from the group consisting of thionyl groups, and one or more hydrogens in the substituents can be replaced with deuterium.

In the present invention, the heterocyclic compound represented by the formula A' has an Ar ₁ to Ar ₃ ring centered on a nitrogen atom bonded to the nitrogen atom, and the Ar ₂ ring is bonded to the Ar ₁ ring and the Ar ₃ ring. At least one of Ar ₁ to Ar ₃ is a phenanthrene ring represented by the structural formula Q, and at least one of R ₁ to R ₁₀ in the phenanthrene ring is a substituent other than hydrogen or deuterium.

In addition, the present invention includes a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one heterocyclic compound represented by Formula A according to the present invention. Provides that the organic light emitting device according to the present invention can exhibit low voltage driving, high efficiency, and long life characteristics.

Meanwhile, in the present invention, “(the organic layer) includes one or more organic compounds” means “(the organic layer) contains one type of organic compound within the scope of the present invention or two or more different types of organic compounds within the scope of the organic compound.” It can be interpreted as “may include compounds.”

At this time, the organic layer in the organic light-emitting device of the present invention includes, in addition to the light-emitting layer, 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, an electron injection function, and It may additionally include at least one layer selected from a functional layer having an electron transport function and a hole blocking layer, and at least one of the organic layers may include one or more heterocyclic compounds represented by Formula A. there is.

As a more preferred embodiment of the present invention, the present invention includes a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes a light emitting layer including a host and a dopant; and at least one layer selected from the group consisting of 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. It is possible to provide an organic light-emitting device containing one or more types of the heterocyclic compound according to the present invention, and in this case, the heterocyclic compound represented by Formula A according to the present invention can be used as a red phosphorescent host.

Meanwhile, in the present invention, a dopant material may be used in the light emitting layer in addition to a host. When the light-emitting layer includes a host and a dopant, the content of the dopant can 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.

As a dopant compound included in the light-emitting layer in the present invention, the dopant is not a fluorescent dopant material that only transitions to a singlet state using the Forster energy transfer method in the existing host-dopant system, but a singlet dopant material. Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Re, using the Dexter Energy transfer method that transfers without distinguishing between and triplet states. It includes a phosphorescent dopant material of a metal complex containing one or more metals selected from Pd, etc., and known dopant materials can be used without particular restrictions as long as they emit light from triplet excitons.

Preferably, an organometallic compound containing a transition metal can be used as a phosphorescent dopant, and the transition metal complex used in this case can be selected from Ir, Pt, and Pd, and specific examples include Ir(ppy) ₃ , Ir( ppy) ₂ acac, Ir(Bt) ₂ acac, Ir(MDQ) ₂ acac, Ir(mppy) ₃ , Ir(piq) _{3, Ir} (piq) ₂ acac, _Ir (pq) ₂ acac, Ir(mpp) ₂ acac, F ₂ Irpic, (F ₂ ppy) ₂ Ir(tmd), Ir(ppy) ₂ tmd, Ir(pmi) ₃ , Ir(pmb) ₃ , FCNIr, FCNIrpic, FIr6, FIrN4, FIrpic, PtOEP, Ir( chpy) ₃ , P0-01(C ₃₁ H ₂₃ IrN ₂ O ₂ S ₂ ), Ir(ppz) _3, Ir(dfppz) _3, PtNON, Pt-10, Pt-11, etc. It is not limited thereto, and more preferably PtOEP, Ir(Bt) ₂ acac, Ir(MDQ) ₂ acac, Ir(piq) ₃ , Ir(piq) ₂ acac, Ir(pq) ₂ acac used as a red phosphorescent dopant. etc. may be used, but are not limited thereto.

As a more preferred embodiment of the present invention, the organic layer interposed between the first electrode and the second electrode includes a light-emitting layer, and the host in the light-emitting layer is a compound different from the above in addition to one compound represented by Formula A. One or more host compounds may be used mixed or laminated. That is, the host according to the present invention further includes one or more different additional host compounds in addition to the one compound represented by Formula A, and two or more host compounds may be mixed or stacked.

Here, in addition to the one compound represented by Formula A, one or more additional host compounds are additionally included, and when two or more host compounds are mixed or stacked and used, more preferably, the additional host is an electron acceptor. Compounds having a moiety may be used, High efficiency due to the advantage of minimizing current loss by limiting the recombination area to the interface of the two hosts due to high hole injection resulting from mixing or stacking with Chemical Formula A having an amine group, which is an electron donor moiety, and the HOMO/LUMO level of the electron injection barrier. , long-life organic light-emitting devices can be implemented.

At this time, compounds having the electron accepting moiety receive electrons from the outside, such as azine compounds, which are nitrogen-containing aromatic heterocycles such as pyridine, pyrimidine, and triazine, and compounds substituted with a cyano group (-CN) in the molecule. As a compound having a moiety that has an environment that is easy to receive, Preferably a heteroaryl group containing 1 to 3 N (nitrogen) elements in the molecule; Alternatively, it may include a compound containing an aryl group containing 1 to 3 cyano groups (-CN) in the molecule.

In addition, the light-emitting layer may further include various hosts and various dopant materials in addition to the dopant and host. Preferably, the dopant in the light-emitting layer of the organic light-emitting device is different from the organic metal compound containing the transition metal. , one or more dopant compounds containing boron may be used in a mixture or stack.

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

1 is a diagram showing the structure of an organic light-emitting device according to an embodiment of the present invention.

As shown in Figure 1, the organic light emitting device according to an embodiment of the present invention 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) in sequential order, wherein the anode is a first electrode, the cathode is a second electrode, a hole transport layer is provided between the anode and the light-emitting layer, and an electron transport layer is provided between the light-emitting layer and the cathode. Applies to organic light emitting devices.

In addition, the organic light emitting device according to an embodiment of the present invention includes a hole injection layer 30 between the anode 20 and the hole transport layer 40, and an electron transport layer 60 and the cathode 80. An injection layer 70 may be included.

The organic light-emitting device of the present invention and its manufacturing method will be described with reference to FIG. 1 as follows.

First, the positive electrode (anode) material is coated on the upper part of the substrate 10 to form the positive electrode 20. Here, as the substrate 10, a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO), which are transparent and have excellent conductivity, are used as materials for the anode electrode.

The hole injection layer 30 is formed by vacuum heat deposition or spin coating of a hole injection layer material on the upper electrode of the anode 20. Next, a hole transport layer 40 is formed on the top of the hole injection layer 30 by vacuum thermal evaporation or spin coating of a hole transport layer material.

The hole injection layer material can be used without particular restrictions as long as it is commonly used in the industry, 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 ] can be used, etc. However, the present invention is not necessarily limited to this.

Additionally, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, 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.

Meanwhile, in the present invention, an electron blocking layer may be additionally formed on the hole transport layer. The electron blocking layer is a layer to improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole transport layer, and can be formed in an appropriate portion between the light-emitting layer and the hole injection layer. and may preferably be formed between the light emitting layer and the hole transport layer.

Subsequently, the light emitting layer 50 may be laminated on the hole transport layer 40 or the electron blocking layer using a vacuum deposition method or a spin coating method.

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

Additionally, according to a specific example of the present invention, the thickness of the light-emitting layer is preferably 50 to 2,000 Å.

In the present invention, a thin film of a hole blocking layer (not shown) can be selectively formed on the organic light emitting layer 50 using a vacuum deposition method or a spin coating method.

The hole blocking layer serves to prevent this problem by using a material with a very low HOMO (Highest Occupied Molecular Orbital) level because the lifespan and efficiency of the device are reduced when holes pass through the light emitting layer and flow into the cathode. At this time, the hole blocking material used is not particularly limited, but must have electron transport ability and a higher ionization potential than the light-emitting compound. Materials used in the hole blocking layer include BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq and any one selected from Formulas 1001 to 1007 may be used, but are not limited thereto.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

Formula 1001 Formula 1002 Formula 1003

Formula 1004 Formula 1005 Formula 1006

Chemical formula 1007

Meanwhile, the electron transport layer 60 is deposited on the light emitting layer or the hole blocking layer through a vacuum deposition method or a spin coating method.

Meanwhile, in the present invention, as the material for the electron transport layer, a known electron transport material that functions to stably transport electrons injected from an electron injection electrode (cathode) can be used. Examples of known electron transport materials include quinoline derivatives, especially tris(8-quinolinolate) aluminum (Alq ₃ ), Liq, TAZ, BAlq, beryllium bis(benzoquinolin-10-noate) Materials such as -10-olate: Bebq2), Compound 201, Compound 202, BCP, and oxadiazole derivatives such as PBD, BMD, and BND may be used, but are not limited thereto.

TAZ BAlq

<Compound 201> <Compound 202> BCP

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 that has the function of facilitating injection of electrons from the cathode, can be laminated on the top of the electron transport layer. This is a special material. No restrictions.

As the electron injection layer forming material, any material known as an electron injection layer forming material such as CsF, NaF, LiF, Li ₂ O, BaO, etc. can be used. The deposition conditions for the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions that are substantially the same as those for forming the hole injection layer.

The thickness of the electron injection layer may be about 1 Å to about 100 Å or 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.

Additionally, in the present invention, the cathode may be made of a material with a low work function to facilitate electron injection. Lithium (Li), magnesium (Mg), calcium (Ca), or their alloys aluminum (Al), aluminum-lithium (Al-Li), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) etc., or a transmission type cathode using ITO or IZO can be used.

Additionally, in the present invention, one or more layers selected from among the above layers may be formed by a single molecule deposition process or a solution process.

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

Additionally, the organic light emitting device in the present invention may include a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; and devices for single-color or white flexible lighting; Vehicle display devices; and a display device for virtual or augmented reality.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for illustrating the present invention in more detail, and it will be apparent to those skilled in the art that the scope of the present invention is not limited thereto.

(Example)

합성예 1. [화합물 161]의 합성Synthesis Example 1. Synthesis of [Compound 161]

Synthesis Example 1-1. Synthesis of A-1

<A-1a> <A-1b> <A-1>

Into the reactor, add 200 g of <A-1a>, 110.5 g of <A-1b>, 12.6 g of tetrakis(triphenylphosphine)palladium(0), 150.6 g of potassium carbonate, 800 mL of toluene, 800 mL of ethanol, and 600 mL of water. It was added and the temperature was raised to 80°C. After 16 hours, it was cooled to room temperature, and the solid produced during the reaction was filtered. The solution dissolved by adding monochlorobenzene and heating was filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain <A-1>. (129 g, 62.3%)

Synthesis Example 1-2. Synthesis of A-2

<A-1> <A-2>

57.2 g of potassium tertiary butoxide and 645 mL of tetrahydrofuran were added to the nitrogen-purged reactor and stirred. It was cooled to -20°C, and 174.6 g of (methoxymethyl)triphenylphosphonium chloride was added. After 30 minutes, a solution of 129 g of <A-1> and 645 mL of tetrahydrofuran was added dropwise. After 2 hours, the temperature was raised to room temperature, and water and ethyl acetate were added to separate the layers. The organic layer was concentrated under reduced pressure and separated using silica gel chromatography to obtain <A-2>. (138 g, 99.6%)

Synthesis Example 1-3. Synthesis of A-3

<A-2> <A-3>

142 g of <A-2> and 1700 mL of methylene chloride were added to the reactor, and 14.2 mL of Eaton's reagent was added dropwise. After 2 hours, the reaction solution was concentrated under reduced pressure and recrystallized to obtain <A-3>. (100 g, 76.4%)

Synthesis Example 1-4. Synthesis of [Compound 161]

<A-3> <A-4a> [Compound 161]

Into the nitrogen-purged reactor, 5.5 g of <A-3>, 4.66 g of <A-4a>, 0.15 g of bis(tri-tertiary butylphosphine)palladium(0), 2.81 g of sodium tertiary butoxide, and 55 mL of toluene were added. And the temperature was raised to 110°C. After 4 hours, it was cooled to room temperature, and then water and ethyl acetate were added to separate the layers. The organic layer was concentrated under reduced pressure and separated using silica gel chromatography to obtain [Compound 161]. (2.5 g, 25.3%)

MS (MALDI-TOF): m/z 674.24 [M ⁺ ]

합성예 2. [화합물 80]의 합성Synthesis Example 2. Synthesis of [Compound 80]

Synthesis Example 2-1. Synthesis of B-1

<B-1a> <A-1b> <B-1>

<B-1> was obtained by synthesis in the same manner, except that <B-1a> was used instead of <A-1a> used in Synthesis Example 1-1. (yield 62.3%)

Synthesis Example 2-2. Synthesis of B-2

<B-1> <B-2>

<B-2> was obtained by synthesis in the same manner, except that <B-1> was used instead of <A-1> used in Synthesis Example 1-2. (yield 99.6%)

Synthesis Example 2-3. Synthesis of B-3

<B-2> <B-3>

<B-3> was obtained by synthesis in the same manner, except that <B-2> was used instead of <A-2> used in Synthesis Example 1-3. (yield 76.4%)

Synthesis Example 2-4. Synthesis of [Compound 80]

<B-3> <A-4a> [Compound 80]

[Compound 80] was obtained by synthesis in the same manner, except that <B-3> was used instead of <A-3> used in Synthesis Example 1-4. (yield 46.6%)

MS (MALDI-TOF): m/z 674.24 [M ⁺ ]

합성예 3. [화합물 106]의 합성Synthesis Example 3. Synthesis of [Compound 106]

Synthesis Example 3-1. Synthesis of [Compound 106]

<B-3> <C-1a> [Compound 106]

[Compound 106] was synthesized in the same manner, except that <B-3> was used instead of <A-3> and <C-1a> was used instead of <A-4a> in Synthesis Example 1-4. got it (yield 36.2%)

MS (MALDI-TOF): m/z 674.24 [M ⁺ ]

합성예 4. [화합물 32]의 합성Synthesis Example 4. Synthesis of [Compound 32]

Synthesis Example 4-1. Synthesis of [Compound 32]

<B-3> <D-1a> [Compound 32]

[Compound 32] was synthesized in the same manner, except that <B-3> was used instead of <A-3> used in Synthesis Example 1-4, and <D-1a> was used instead of <A-4a>. got it (yield 37.2%)

MS (MALDI-TOF): m/z 674.24 [M ⁺ ]

합성예 5. [화합물 7]의 합성Synthesis Example 5. Synthesis of [Compound 7]

Synthesis Example 5-1. Synthesis of E-1

<B-1a> <E-1a> <E-1>

<E-1> was synthesized in the same manner except that <B-1a> was used instead of <A-1a> and <E-1a> was used instead of <A-1b> in Synthesis Example 1-1. got it (yield 92.1%)

Synthesis Example 5-2. Synthesis of E-2

<E-1> <E-2>

<E-2> was obtained by synthesis in the same manner, except that <E-1> was used instead of <A-1> used in Synthesis Example 1-2. (yield 82.8%)

Synthesis Example 5-3. Synthesis of E-3

<E-3> was obtained by synthesis in the same manner, except that <E-2> was used instead of <A-2> used in Synthesis Example 1-3. (yield 90%)

Synthesis Example 5-4. Synthesis of [Compound 7]

<E-3> <E-4a> [Compound 7]

[Compound 7] was synthesized in the same manner, except that <E-3> was used instead of <A-3> used in Synthesis Example 1-4, and <E-4a> was used instead of <A-4a>. got it (yield 56.9%)

MS (MALDI-TOF): m/z 508.19 [M ⁺ ]

합성예 6. [화합물 113]의 합성Synthesis Example 6. Synthesis of [Compound 113]

Synthesis Example 6-1. Synthesis of [Compound 113]

<A-3> <D-1a> [Compound 113]

[Compound 113] was obtained by synthesis in the same manner except that <D-1a> was used instead of <A-4a> used in Synthesis Example 1-4. (yield 60.8%)

MS (MALDI-TOF): m/z 674.24 [M ⁺ ]

합성예 7. [화합물 141]의 합성Synthesis Example 7. Synthesis of [Compound 141]

Synthesis Example 7-1. Synthesis of [Compound 141]

<A-3> <G-1a> [Compound 141]

[Compound 141] was obtained by synthesis in the same manner except that <G-1a> was used instead of <A-4a> used in Synthesis Example 1-4. (yield 52.2%)

MS (MALDI-TOF): m/z 674.24 [M ⁺ ]

합성예 8. [화합물 477]의 합성Synthesis Example 8. Synthesis of [Compound 477]

Synthesis Example 8-1. Synthesis of H-1

<B-1a> <H-1a> <H-1>

50 g of <B-1a>, 62.5 g of aluminum chloride, and 1000 mL of methylene chloride were added to the nitrogen-purged reactor, cooled to 0°C, and then 85.8 g of <H-1a> was added. After 5 minutes, the temperature was raised to room temperature, and then a saturated aqueous solution of sodium bicarbonate was added to separate the layers. After concentrating the organic layer under reduced pressure, toluene was added and heated to dissolve the solution, which was filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain <H-1>. (28.9 g, 34.2%)

Synthesis Example 8-2. Synthesis of H-2

<H-1> <A-1b> <H-2>

<H-2> was obtained by synthesis in the same manner, except that <H-1> was used instead of <A-1a> used in Synthesis Example 1-1. (yield 61%)

Synthesis Example 8-3. Synthesis of H-3

<H-2> <H-3>

<H-3> was obtained by synthesis in the same manner, except that <H-2> was used instead of <A-1> used in Synthesis Example 1-2. (yield 97.7%)

Synthesis Example 8-4. Synthesis of H-4

<H-3> <H-4>

<H-4> was obtained by synthesis in the same manner, except that <H-3> was used instead of <A-2> used in Synthesis Example 1-3. (yield 80.9%)

Synthesis Example 8-5. Synthesis of [Compound 477]

<H-4> <A-4a> [Compound 477]

[Compound 477] was obtained by synthesis in the same manner, except that <H-4> was used instead of <A-3> used in Synthesis Example 1-4. (yield 35.8%)

MS (MALDI-TOF): m/z 895.45 [M ⁺ ]

합성예 9. [화합물 49]의 합성Synthesis Example 9. Synthesis of [Compound 49]

Synthesis Example 9-1. Synthesis of [Compound 49]

<B-3> <I-1a> [Compound 49]

[Compound 49] was synthesized in the same manner except that <B-3> was used instead of <A-3> and <I-1a> was used instead of <A-4a> in Synthesis Example 1-4. got it (yield 60.3%)

MS (MALDI-TOF): m/z 714.27 [M ⁺ ]

합성예 10. [화합물 111]의 합성Synthesis Example 10. Synthesis of [Compound 111]

Synthesis Example 10-1. Synthesis of [Compound 111]

<A-3> <J-1a> [Compound 111]

[Compound 111] was obtained by synthesis in the same manner except that <J-1a> was used instead of <A-4a> used in Synthesis Example 1-4. (yield 56.7%)

MS (MALDI-TOF): m/z 674.24 [M ⁺ ]

합성예 11. [화합물 81]의 합성Synthesis Example 11. Synthesis of [Compound 81]

Synthesis Example 11-1. Synthesis of [Compound 81]

<B-3> <K-1a> [Compound 81]

[Compound 81] was synthesized in the same manner, except that <B-3> was used instead of <A-3> used in Synthesis Example 1-4, and <K-1a> was used instead of <A-4a>. got it (yield 56.3%)

MS (MALDI-TOF): m/z 700.29 [M ⁺ ]

합성예 12. [화합물 47]의 합성Synthesis Example 12. Synthesis of [Compound 47]

Synthesis Example 12-1. Synthesis of [Compound 47]

<B-3> <L-1a> [Compound 47]

[Compound 47] was synthesized in the same manner, except that <B-3> was used instead of <A-3> used in Synthesis Example 1-4, and <L-1a> was used instead of <A-4a>. got it (yield 55.8%)

MS (MALDI-TOF): m/z 714.27 [M ⁺ ]

합성예 13. [화합물 243]의 합성Synthesis Example 13. Synthesis of [Compound 243]

Synthesis Example 13-1. Synthesis of [Compound 243]

<A-3> <M-1a> [Compound 243]

[Compound 243] was obtained by synthesis in the same manner except that <M-1a> was used instead of <A-4a> used in Synthesis Example 1-4. (yield 54.5%)

MS (MALDI-TOF): m/z 740.32 [M ⁺ ]

합성예 14. [화합물 21]의 합성Synthesis Example 14. Synthesis of [Compound 21]

Synthesis Example 14-1. Synthesis of [Compound 21]

<B-3> <N-1a> [Compound 21]

[Compound 21] was synthesized in the same manner, except that <B-3> was used instead of <A-3> used in Synthesis Example 1-4, and <N-1a> was used instead of <A-4a>. got it (yield 60%)

MS (MALDI-TOF): m/z 674.24 [M ⁺ ]

합성예 15. [화합물 420]의 합성Synthesis Example 15. Synthesis of [Compound 420]

Synthesis Example 15-1. Synthesis of O-1

<E-3> <O-1a> <O-1>

Into the nitrogen-purged reactor, add 7 g of <E-3>, 6.62 g of <O-1a>, 0.21 g of palladium acetate (II), 9.88 g of potassium phosphate, 0.99 g of S-phos, and 70 mL of 1,4-dioxane and add 100 mL. The temperature was raised to °C. After 4 hours, it was cooled to room temperature, and the solid obtained by filtration was dissolved by adding toluene and heating. The solution was filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain <O-1>. (6 g, 68.9%)

Synthesis Example 15-2. Synthesis of [Compound 420]

<O-1> <O-2a> [Compound 420]

In a nitrogen-purged reactor, 6.14 g of <O-1>, 4.84 g of <O-2a>, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 3.63 g of potassium carbonate, 25 mL of toluene, 18 mL of ethanol, and water. 18 mL was added and the temperature was raised to 80°C. After 4 hours, it was cooled to room temperature, and dichlorobenzene was added to the solid obtained by filtration. The solution was heated and dissolved, filtered using silica gel, concentrated under reduced pressure, and recrystallized to obtain [Compound 420]. (3 g, 34.5%)

MS (MALDI-TOF): m/z 662.21 [M ⁺ ]

합성예 16. [화합물 416]의 합성Synthesis Example 16. Synthesis of [Compound 416]

Synthesis Example 16-1. Synthesis of P-1

<B-3> <O-1a> <P-1>

<P-1> was obtained by synthesis in the same manner, except that <B-3> was used instead of <E-3> used in Synthesis Example 15-1. (yield 65.1%)

Synthesis Example 16-2. Synthesis of [Compound 416]

<P-1> <P-2a> [Compound 416]

[Compound 416] was synthesized in the same manner except that <P-1> was used instead of <O-1> and <P-2a> was used instead of <O-2a> in Synthesis Example 15-2. got it (yield 64.7%)

MS (MALDI-TOF): m/z 572.20 [M ⁺ ]

실시예 1 내지 23 : 유기발광소자의 제조Examples 1 to 23: Production of organic light-emitting devices

The ITO glass was patterned so that the light emitting area was 2 mm x 2 mm in size and then cleaned. After mounting the ITO glass in a vacuum chamber and setting the base pressure to ¹ NPD] (1500 Å) was deposited. The light-emitting layer is formed by mixing the host compound prepared according to the present invention and either [ET-RH] or [HT-RH] at a weight ratio of 5:5 and forming a film (400 Å) with dopant [RD] (5 wt%). Then, [ET]: Liq = 1: 1 (300 Å) was formed as an electron transport layer, Liq (10 Å) was sequentially deposited as an electron injection layer, and Al (1000 Å) was formed as a cathode to produce an organic light-emitting device. Produced. The emission characteristics of the organic light emitting device were measured at 0.4 mA, and the measurement results are shown in Table 1 below.

[HATCN] [NPD] [RD]

[ET] [Liq] [ET-RH]

[HT-RH]

비교예 1 내지 5Comparative Examples 1 to 5

The organic light emitting device for the comparative example was manufactured and tested in the same manner, except that [RH-1] to [RH-3] below were used instead of the compound according to the present invention used as the host in the device structure of the above example. The emission characteristics of the organic light emitting device were measured at 0.4 mA, and the measurement results are shown in Table 1 below. Here, the structures of [RH-1] to [RH-3] are as follows.

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

구 분division	호스트 (1:1)host (1:1)		구동 전압 (V)Driving Voltage (V)	전류 효율 (cd/A)electric current efficiency (cd/A)	수명 (T95,hr)life span (T95,hr)	발광색 (color)Luminous color (color)
실시예 1Example 1	화합물 7Compound 7	ET-RHET-RH	3.883.88	25.725.7	250250	적색Red
실시예 2Example 2	화합물 21Compound 21	ET-RHET-RH	3.533.53	28.928.9	300300	적색Red
실시예 3Example 3	화합물 32Compound 32	ET-RHET-RH	3.663.66	28.128.1	450450	적색Red
실시예 4Example 4	화합물 47Compound 47	ET-RHET-RH	3.593.59	28.828.8	310310	적색Red
실시예 5Example 5	화합물 49Compound 49	ET-RHET-RH	3.663.66	28.428.4	400400	적색Red
실시예 6Example 6	화합물 80Compound 80	ET-RHET-RH	3.663.66	27.227.2	400400	적색Red
실시예 7Example 7	화합물 81Compound 81	ET-RHET-RH	3.623.62	28.728.7	356356	적색Red
실시예 8Example 8	화합물 106Compound 106	ET-RHET-RH	3.873.87	24.824.8	250250	적색Red
실시예 9Example 9	화합물 111Compound 111	ET-RHET-RH	3.673.67	28.328.3	286286	적색Red
실시예 10Example 10	화합물 113Compound 113	ET-RHET-RH	3.663.66	27.927.9	320320	적색Red
실시예 11Example 11	화합물 141Compound 141	ET-RHET-RH	3.823.82	27.227.2	308308	적색Red
실시예 12Example 12	화합물 161Compound 161	ET-RHET-RH	3.713.71	27.627.6	380380	적색Red
실시예 13Example 13	화합물 193Compound 193	ET-RHET-RH	3.593.59	28.428.4	333333	적색Red
실시예 14Example 14	화합물 218Compound 218	ET-RHET-RH	3.633.63	28.528.5	325325	적색Red
실시예 15Example 15	화합물 243Compound 243	ET-RHET-RH	3.563.56	28.828.8	320320	적색Red
실시예 16Example 16	화합물 266Compound 266	ET-RHET-RH	3.623.62	27.927.9	352352	적색Red
실시예 17Example 17	화합물 301Compound 301	ET-RHET-RH	3.623.62	27.727.7	351351	적색Red
실시예 18Example 18	화합물 355Compound 355	ET-RHET-RH	3.583.58	27.827.8	343343	적색Red
실시예 19Example 19	화합물 416Compound 416	HT-RHHT-RH	3.703.70	26.926.9	210210	적색Red
실시예 20Example 20	화합물 420Compound 420	HT-RHHT-RH	3.623.62	27.827.8	287287	적색Red
실시예 21Example 21	화합물 467Compound 467	HT-RHHT-RH	3.613.61	27.527.5	240240	적색Red
실시예 22Example 22	화합물 468Compound 468	HT-RHHT-RH	3.633.63	27.727.7	290290	적색Red
실시예 23Example 23	화합물 477Compound 477	ET-RHET-RH	3.613.61	26.626.6	250250	적색Red
비교예 1Comparative Example 1	RH-1RH-1	ET-RHET-RH	5.105.10	13.113.1	8484	적색Red
비교예 2Comparative Example 2	RH-2RH-2	ET-RHET-RH	4.324.32	19.019.0	110110	적색Red
비교예 3Comparative Example 3	RH-3RH-3	ET-RHET-RH	5.035.03	15.215.2	7575	적색Red
비교예 4Comparative Example 4	RH-1RH-1	HT-RHHT-RH	5.215.21	12.712.7	1313	적색Red
비교예 5Comparative Example 5	RH-3RH-3	HT-RHHT-RH	5.315.31	11.711.7	99	적색Red

As shown in [Table 1], the heterocyclic compound according to the present invention appears to have better low-voltage driving, high efficiency, and long life characteristics compared to Comparative Examples 1 to 5 according to the prior art, so that the organic It shows high applicability as a light-emitting device.

Claims

A heterocyclic compound represented by the following formula (A).

[Formula A] [Structural Formula Q]

In the above formula A and structural formula Q,

Ar 1 to Ar 3 are the same or different from each other, and each independently represents 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, or a substituted or unsubstituted carbon number. Among the aromatic hydrocarbon rings in which 8 to 50 aliphatic hydrocarbon rings are condensed, the substituted or unsubstituted aromatic heterocycles in which 2 to 50 carbon atoms are condensed, and the aromatic heterocycles in which substituted or unsubstituted aliphatic hydrocarbon rings are condensed in 5 to 50 carbon atoms. Any one selected, wherein at least one of Ar 1 to Ar 3 has the structural formula Q;

When Ar 1 or Ar 3 has structural formula Q, R 1 of structural formula Q Among R 4 to R 4 , the two substituents adjacent to each other are single bonds bonding to the nitrogen atom (N) and Ar 2 in Formula A, respectively,

When Ar 2 has the structural formula Q, the three adjacent substituents among R 1 to R 4 of the structural formula Q are single bonds bonding to the nitrogen atom (N), Ar 1 and Ar 3 in the formula A, respectively,

The R 1 to R 10 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group. Alkynyl group with 2 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group with 5 to 30 carbon atoms, substituted or An 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 heteroaryl group having 7 to 30 carbon atoms, A cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed, a heterocycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring is condensed in 6 to 30 carbon atoms, A substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 1 to 30 carbon atoms. alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Select from a heteroarylthio group, 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, or a halogen group. Any one of them,

At least one of R 1 to R 10 of the structural formula Q is any one of the following structural formulas H and I,

[Structural Formula H] [Structural Formula I]

In structural formula H and structural formula I,

L 1 and L 2 are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, and a substituted or unsubstituted group. It is any one selected from arylene groups in which an aliphatic hydrocarbon ring having 8 to 50 carbon atoms is condensed,

The m is an integer from 0 to 4, but when m is 2 or more, each linking group L 1 is the same or different from each other,

The n is an integer from 0 to 4, but when n is 2 or more, each linking group L 2 is the same or different from each other,

In the structural formula I , X 1 to

When X 1 to X 6 includes a plurality of CR 13 , each CR 13 is the same or different,

R 11 to R 13 are the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkyl group. Alkynyl group with 2 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group with 5 to 30 carbon atoms, substituted or An 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 heteroaryl group having 7 to 30 carbon atoms, A cycloalkyl group in which an aromatic hydrocarbon ring is condensed, a cycloalkyl group in which a substituted or unsubstituted aromatic heterocycle having 5 to 30 carbon atoms is condensed, a heterocycloalkyl group in which a substituted or unsubstituted aromatic hydrocarbon ring is condensed in 6 to 30 carbon atoms, A substituted or unsubstituted aryl group having a condensed aliphatic hydrocarbon ring having 8 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having a condensed aliphatic hydrocarbon ring having 1 to 30 carbon atoms. alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted cycloalkyloxy group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaryloxy group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylthio group with 1 to 30 carbon atoms, substituted or unsubstituted arylthio group with 6 to 30 carbon atoms, substituted or unsubstituted cycloalkylthio group with 3 to 30 carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Select from a heteroarylthio group, a substituted or unsubstituted amine group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group having 1 to 30 carbon atoms, a germanium group having 1 to 30 carbon atoms, a nitro group, a cyano group, or a halogen group. It's one of those things,

In the structural formula I , when X 1 to ,

In the structural formula Q, R 1 to R 10 may each be connected to adjacent groups to additionally form an alicyclic or aromatic monocyclic or polycyclic ring,

In the formula A, structural formula Q, structural formula H and structural formula I, 'substituted' in 'substituted or unsubstituted' means deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group with 1 to 30 carbon atoms, and 1 to 30 carbon atoms. halogenated alkyl group, alkenyl group with 2 to 30 carbon atoms, alkynyl group with 2 to 30 carbon atoms, cycloalkyl group with 3 to 30 carbon atoms, heteroalkyl group with 1 to 30 carbon atoms, aryl group with 6 to 30 carbon atoms, and 7 to 30 carbon atoms. Arylalkyl group, alkylaryl group with 7 to 30 carbon atoms, heteroaryl group with 2 to 30 carbon atoms, heteroarylalkyl group with 3 to 30 carbon atoms, alkylheteroaryl group with 3 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, 7 carbon atoms A cycloalkyl group with a condensed aromatic hydrocarbon ring having 30 to 30 carbon atoms, a cycloalkyl group with a fused aromatic heterocycle having 5 to 30 carbon atoms, a heterocycloalkyl group with a fused aromatic hydrocarbon ring having 6 to 30 carbon atoms, a heterocycloalkyl group with 7 to 30 carbon atoms, Aryl group with a condensed aliphatic hydrocarbon ring, a heteroaryl group with a condensed aliphatic hydrocarbon ring having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group with a condensed aliphatic heteroring having 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group with 5 to 30 carbon atoms condensed with aliphatic heteroring, amine group with 1 to 30 carbon atoms, silyl group with 1 to 30 carbon atoms, germanium group with 1 to 30 carbon atoms, aryloxy group with 6 to 30 carbon atoms and 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.
According to clause 1,

A heterocyclic compound characterized in that the remaining ring other than structural formula Q among Ar 1 to Ar 3 of the formula A is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 12 carbon atoms.
According to clause 1,

The compound represented by Formula A is a heterocyclic compound characterized in that it contains at least one deuterium.
According to clause 1,

A heterocyclic compound wherein Ar 1 or Ar 3 has structural formula Q.
According to clause 1,

A heterocyclic compound wherein Ar 2 has structural formula Q.
According to clause 1,

A heterocyclic compound, characterized in that only one of R 5 to R 8 of the structural formula Q is a substituent represented by the structural formula H.
According to clause 1,

A heterocyclic compound characterized in that only one of R 5 to R 8 of the structural formula Q is a substituent represented by the structural formula I.
According to clause 1,

The ring containing X 1 to heterocyclic compound.
According to clause 1,

The compound represented by Formula A is a heterocyclic compound selected from the group represented by numbers 1 to 486 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

88 89 90

91 92 93

94 95 96

97 98 99

100 101 102

103 104 105

106 107 108

109 110 111

112 113 114

115 116 117

118 119 120

121 122 123

124 125 126

127 128 129

130 131 132

133 134 135

136 137 138

139 140 141

142 143 144

145 146 147

148 149 150

151 152 153

154 155 156

157 158 159

160 161 162

163 164 165

166 167 168

169 170 171

172 173 174

175 176 177

178 179 180

181 182 183

184 185 186

187 188 189

190 191 192

193 194 195

196 197 198

199 200 201

202 203 204

205 206 207

208 209 210

211 212 213

214 215 216

217 218 219

220 221 222

223 224 225

226 227 228

229 230 231

232 233 234

235 236 237

238 239 240

241 242 243

244 245 246

247 248 249

250 251 252

253 254 255

256 257 258

259 260 261

262 263 264

265 266 267

268 269 270

271 272 273

274 275 276

277 278 279

280 281 282

283 284 285

286 287 288

289 290 291

292 293 294

295 296 297

298 299 300

301 302 303

304 305 306

307 308 309

310 311 312

313 314 315

316 317 318

319 320 321

322 323 324

325 326 327

328 329 330

331 332 333

334 335 336

337 338 339

340 341 342

343 344 345

346 347 348

349 350 351

352 353 354

355 356 357

358 359 360

361 362 363

364 365 366

367 368 369

370 371 372

373 374 375

376 377 378

379 380 381

382 383 384

385 386 387

388 389 390

391 392 393

394 395 396

397 398 399

400 401 402

403 404 405

406 407 408

409 410 411

412 413 414

415 416 417

418 419 420

421 422 423

424 425 426

427 428 429

430 431 432

433 434 435

436 437 438

439 440 441

442 443 444

445 446 447

448 449 450

451 452 453

454 455 456

457 458 459

460 461 462

463 464 465

466 467 468

469 470 471

472 473 474

475 476 477

478 479 480

481 482 483

484 485 486
first electrode;

a second electrode opposite the first electrode; and

It includes 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,

The host is an organic light-emitting device characterized in that it contains at least one heterocyclic compound according to any one of claims 1 to 9.
According to clause 10,

In addition to the light emitting layer, the organic layer includes 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, An organic light emitting device, characterized in that it additionally includes at least one layer selected from hole blocking layers.
According to clause 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 stacking one or more types of host compounds different from the heterocyclic compound.
According to clause 10,

An organic light-emitting device, characterized in that an organic metal compound containing a transition metal is used as a dopant in the light-emitting layer of the organic light-emitting device.
According to clause 13,

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 or stacking one or more different boron-containing dopant compounds in addition to the organic metal compound containing the transition metal.
According to clause 10,

An organic light-emitting device, characterized in that the heterocyclic compound used in the host is used as a red phosphorescent host.
According to clause 10,

The organic light emitting device may include a flat panel display device; flexible display device; Devices for monochromatic or white flat lighting; Devices for flexible lighting in single color or white; Vehicle display devices; and a display device for virtual or augmented reality. An organic light emitting device used in any one device selected from the group consisting of: