KR20220036329A - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic light-emitting device containing the same, and more specifically, to an organic electroluminescent device with low driving voltage and significantly improved luminous efficiency and lifespan.

Description

Organic compounds and organic electroluminescent devices containing the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to organic compounds and organic electroluminescent devices containing the same.

Organic electroluminescent devices (OLEDs) have a simpler structure and various advantages in the manufacturing process compared to other flat panel display devices such as existing liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs). It has excellent high brightness and viewing angle characteristics, fast response speed, and low driving voltage, and is being actively developed and commercialized to be used as a light source for flat displays such as wall-mounted TVs, backlight of displays, lighting, and billboards.

The first organic EL device was reported by C. W. Tang of Eastman Kodak and others (C. W. Tang, S. A. Vanslyke, Applied Physics Letters, Volume 51, Page 913, 1987), and its light-emitting principle is generally: When a voltage is applied, the holes injected from the anode and the electrons injected from the cathode recombine to form an exciton, an electron-hole pair, and the energy of this exciton is converted into light by transferring it to the light-emitting material.

More specifically, the organic electroluminescent device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and one or more organic layers between the two electrodes. At this time, the organic electroluminescent device consists of a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), or an electron transport layer (ETL) from the anode. It is laminated in the order of the injection layer (EIL), and to increase the efficiency of the light emitting layer, a hole transport auxiliary layer or a hole blocking layer (HBL) may be additionally included on the front and back of the light emitting layer, respectively.

Materials used as organic layers in organic electric 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 most problematic issues with organic electroluminescent devices are lifespan and efficiency, and as displays become larger in area, these efficiency and lifespan issues must be resolved. Efficiency, lifespan, and driving voltage are related to each other. As efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. Life expectancy tends to increase.

However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.

In addition, in order to solve the problem of light emission from the hole transport layer in recent organic electroluminescent devices, a light emission auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliaries are required for each light emitting layer (R, G, B). It is time for layered development.

In general, electrons are transferred from the electron transport layer to the light-emitting layer, and holes are transferred from the hole transport layer to the light-emitting layer, and excitons are generated through recombination.

However, the material used in the hole transport layer must have a low HOMO value, so most of them have a low T1 value. This causes excitons generated in the light-emitting layer to pass over to the hole transport layer, resulting in a charge imbalance in the light-emitting layer. This causes light to be emitted at the hole transport layer interface.

When light is emitted from the hole transport layer interface, the color purity and efficiency of the organic electric device are reduced and the lifespan is shortened. Therefore, there is an urgent need to develop a light-emitting auxiliary layer that has a high T1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

(Non-patent Document 1) Krebs, Frederik C., et al. “Synthesis, Structure, and Properties of 4, 8, 12-Trioxa-12c-phospha-4, 8, 12, 12c-tetrahydrodibenzo [cd, mn] pyrene, a Molecular Pyroelectric.” Journal of the American Chemical Society 119.6 (1997): 1208-1216.

The object of the present invention is to provide a novel organic compound and an organic electroluminescent device containing the same.

Another object of the present invention is to provide a novel organic compound that can exhibit a relatively high glass transition temperature and thermal stability.

Another object of the present invention is to exhibit excellent hole transport characteristics, reduce the HOMO energy level difference between the hole transport layer and the light-emitting layer, adjust the hole injection characteristics, reduce hole accumulation at the interface of the light-emitting layer, and reduce the accumulation of holes at the interface of the light-emitting layer, resulting in low driving voltage and light emission. An organic electroluminescent device with significantly improved efficiency and lifespan characteristics can be provided.

In order to achieve the other objects of the present invention, the present invention provides a compound represented by the following formula (1):

[Formula 1]

here,

n, m and p are the same or different from each other and are each independently an integer from 0 to 5,

Ring A, ring B, and ring C are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 5 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms,

X ₁ and X ₂ are the same or different from each other and are each independently selected from the group consisting of N, O and S,

R ₁ to R ₅ are the same or different from each other, and each independently represents hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms. 30 alkyl group, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted alkyl group with 7 to 30 carbon atoms Alkyl group, substituted or unsubstituted aryl group with 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 5 to 60 nuclear atoms, substituted or unsubstituted heteroarylalkyl group with 6 to 30 carbon atoms, substituted or unsubstituted carbon number of 1 to 30 an alkoxy group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkylamino group having 2 to 24 carbon atoms. selected from the group consisting of a heteroarylamino group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and adjacent Groups can be combined with each other to form a substituted or unsubstituted ring,

At least one of R ₁ to R ₅ is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 30 carbon atoms.

In addition, the present invention includes a first electrode; a second electrode opposite the first electrode; It relates to an organic electroluminescent device comprising at least one organic material layer interposed between the first electrode and the second electrode, wherein the at least one organic material layer includes the compound represented by Formula 1.

In the present invention, “hydrogen” refers to hydrogen, light hydrogen, deuterium, or tritium, unless otherwise specified.

In the present invention, the “halogen group” is fluorine, chlorine, bromine, or iodine.

In the present invention, “alkyl” refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc., but are not limited thereto.

In the present invention, “alkenyl” refers to a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

In the present invention, “alkynyl” refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2-propynyl, etc., but are not limited thereto.

In the present invention, “alkylthio” refers to the alkyl group described above bonded through a sulfur linkage (-S-).

In the present invention, “aryl” refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, either a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply attached to each other (pendant) or condensed may also be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, anthryl, fluonyl, dimethylfluorenyl, etc., but are not limited thereto.

In the present invention, “heteroaryl” refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, at least one carbon, preferably 1 to 3 carbons, of the ring is replaced with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply pendant or condensed with each other may be included, and a condensed form with an aryl group may also be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, and indolyl ( Polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, etc., but are not limited thereto.

In the present invention, “aryloxy” is a monovalent substituent represented by RO-, where R refers to aryl having 6 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy, etc., but are not limited thereto.

In the present invention, “alkyloxy” is a monovalent substituent represented by R'O-, where R' refers to alkyl having 1 to 40 carbon atoms and has a linear, branched, or cyclic structure. may include. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

In the present invention, “alkoxy” may be a straight chain, branched chain, or ring chain. The number of carbon atoms of alkoxy is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. It may be possible, but it is not limited to this.

As used herein, “aralkyl” refers to an aryl-alkyl group where aryl and alkyl are defined above. Preferred aralkyl contains lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl, and naphthalenylmethyl. Bonding to the parent moiety is via the alkyl.

In the present invention, “arylamino group” refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.

In the present invention, “alkylamino group” means an amine substituted with an alkyl group having 1 to 30 carbon atoms.

In the present invention, “aralkyl amino group” refers to an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

In the present invention, “heteroarylamino group” refers to an amine group substituted with an aryl group or heterocyclic group having 6 to 30 carbon atoms.

In the present invention, “heteroaralkyl group” refers to an aryl-alkyl group substituted with a heterocyclic group.

In the present invention, “cycloalkyl” refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

In the present invention, “heterocycloalkyl” refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or Se. It is substituted with a hetero atom such as Examples of such heterocycloalkyl include, but are not limited to, morpholine and piperazine.

In the present invention, “alkylsilyl” refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and “arylsilyl” refers to silyl substituted with aryl having 6 to 60 carbon atoms.

In the present invention, “condensed ring” means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

In the present invention, "forming a ring by bonding with adjacent groups" means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means forming a condensation ring thereof.

In the present invention, examples of “aromatic hydrocarbon rings” include phenyl groups, naphthyl groups, and anthracenyl groups, but are not limited to these.

In the present invention, “aliphatic heterocycle” refers to an aliphatic ring containing one or more heteroatoms.

In the present invention, “aromatic heterocycle” refers to an aromatic ring containing one or more heteroatoms.

In the present invention, "substitution" means changing a hydrogen atom bonded to a carbon atom of a compound to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other. The substituents include hydrogen, cyano group, nitro group, halogen group, hydroxy group, alkyl group with 1 to 30 carbon atoms, alkenyl group with 2 to 30 carbon atoms, alkynyl group with 2 to 24 carbon atoms, heteroalkyl group with 2 to 30 carbon atoms, and 6 to 6 carbon atoms. Aralkyl group of 30, aryl group of 5 to 30 carbon atoms, heteroaryl group of 2 to 30 carbon atoms, heteroarylalkyl group of 3 to 30 carbon atoms, alkoxy group of 1 to 30 carbon atoms, alkylamino group of 1 to 30 carbon atoms, 6 to 6 carbon atoms Arylamino group of 30, aralkylamino group of 6 to 30 carbon atoms, heteroarylamino group of 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group of 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group of 6 to 30 carbon atoms and substituted Alternatively, it may be substituted with one or more substituents selected from the group consisting of unsubstituted aryloxy groups having 6 to 30 carbon atoms, but is not limited to the above examples.

The present invention relates to a novel organic compound that can exhibit a relatively high glass transition temperature and thermal stability. The novel organic compound is included as a material for an organic electroluminescent device, exhibits excellent hole transport properties, and has a hole transport layer and a light emitting layer. By reducing the HOMO energy level difference between the two, adjusting the hole injection characteristics, reducing the accumulation of holes at the interface of the light emitting layer, significantly improving low driving voltage, luminous efficiency and lifespan characteristics.

Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily implement it. However, the present invention may be implemented in many different forms and is not limited to the embodiments described herein.

The novel organic compound according to the present invention can exhibit high glass transition temperature and thermal stability, and in particular has a HOMO energy level that facilitates hole transport, making it a hole transport auxiliary layer material for organic electroluminescent devices with excellent hole transport characteristics to the light-emitting layer. can be used as

Although the compound structure of the present invention has the characteristic of reduced crystallinity, the structure forms a three-dimensionally rigid condensed ring, which can reduce molecular mobility. On the other hand, in the case of a single molecule structure rather than a cycloalkyl or aryl structure, the molecule is a non-planar structure, and a non-planar structure such as an alkyl group with a long chain is generally caused by characteristics such as rotational or vibrational movement of the molecule. Energy loss may occur due to motility. As described above, due to the characteristics of the present invention that forms three-dimensionally rigid condensed rings, it has high heat resistance and can reduce energy loss due to mobility.

Specifically, the compound represented by the following formula (1) is as follows:

[Formula 1]

here,

n, m and p are the same or different from each other and are each independently an integer from 0 to 5,

Ring A, ring B, and ring C are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 5 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms,

X ₁ and X ₂ are the same or different from each other and are each independently selected from the group consisting of N, O and S,

R ₁ to R ₅ are the same or different from each other, and each independently represents hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms. 30 alkyl group, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted alkyl group with 7 to 30 carbon atoms Alkyl group, substituted or unsubstituted aryl group with 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 5 to 60 nuclear atoms, substituted or unsubstituted heteroarylalkyl group with 6 to 30 carbon atoms, substituted or unsubstituted carbon number of 1 to 30 an alkoxy group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkylamino group having 2 to 24 carbon atoms. selected from the group consisting of a heteroarylamino group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and adjacent Groups can be combined with each other to form a substituted or unsubstituted ring,

At least one of R ₁ to R ₅ is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 30 carbon atoms.

The compound represented by Formula 1 relates to a compound represented by the following Formula 2:

[Formula 2]

here,

n, m, X ₁ , X ₂ , R ₁ , R ₂ , R ₃ and R ₅ are as defined in Formula 1 above,

q is an integer from 0 to 4,

R ₆ is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 30 carbon atoms.

R ₆ is preferably a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, more preferably a substituted or unsubstituted adamantyl group, but is not limited to the above examples.

The A ring and B ring are the same or different from each other, and are each independently selected from the group consisting of substituents represented by the following formulas (3) to (9).

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

here,

* refers to the part that is combined,

r is an integer from 0 to 5,

s is an integer from 0 to 7,

t, v and a are the same or different from each other and are each independently an integer from 0 to 3,

u is an integer from 0 to 6,

w, x, y and z are the same or different from each other and are each independently an integer from 0 to 4,

X ₃ , X ₅ and _{and ​ ​ ​}

X ₄ is selected from the group consisting of a single bond, O, S, N(R ₂₀ ) and C(R ₂₁ )(R ₂₂ ),

X ₆ is selected from the group consisting of N(R ₂₃ ), O and S,

R ₇ to R ₂₃ are the same or different from each other, and each independently represents hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms. 30 alkyl group, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted alkyl group with 7 to 30 carbon atoms Alkyl group, substituted or unsubstituted aryl group with 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 5 to 60 nuclear atoms, substituted or unsubstituted heteroarylalkyl group with 6 to 30 carbon atoms, substituted or unsubstituted carbon number of 1 to 30 an alkoxy group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkylamino group having 2 to 24 carbon atoms. selected from the group consisting of a heteroarylamino group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and adjacent Groups may be combined with each other to form a substituted or unsubstituted ring.

X ₁ and X ₂ are N.

The compound represented by Formula 1 according to the present invention is selected from the group consisting of the following compounds, but is not limited thereto:

The compound of Formula 1 of the present invention can be usefully used as a hole transport auxiliary layer material.

As the compound of the present invention is used as a hole transport auxiliary layer material in an organic electroluminescent device, the HOMO in the compound can be increased and finely adjusted to optimally control the hole mobility according to the electron mobility injected into the light emitting layer. Contains a substituent.

Due to these characteristics, when the organic compound is used as a material for an organic electroluminescent device, it can exhibit equivalent or superior properties in most device characteristics, such as luminous efficiency and lifespan.

The present invention provides an organic electroluminescent device containing the compound represented by Formula 1 above.

The organic compound of the present invention can be usefully used as a material for a hole transport auxiliary layer.

In addition, the present invention relates to an organic electroluminescent device in which an organic thin film layer consisting of one or multiple layers including at least a light emitting layer is stacked between a cathode and an anode, wherein the organic thin film layer is a hole transport auxiliary layer between the first electrode and the light emitting layer. am.

The hole transport auxiliary layer is a compound represented by Chemical Formula 1.

The organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked, and an electron transport auxiliary layer may be added as needed. Can be laminated.

Below, the organic electroluminescent device of the present invention will be described as an example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention has a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer, an emitting layer (EML), and a cathode (electron injection electrode) are sequentially stacked. It may have, and preferably, may further include a hole transport auxiliary layer between the anode and the light-emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the light-emitting layer. Additionally, an electron transport auxiliary layer may be further included between the cathode and the light emitting layer.

In the method of manufacturing an organic electroluminescent device according to the present invention, an anode material is first coated on the surface of a substrate using a conventional method to form an anode. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and waterproofness. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, can be used as materials for the anode.

Next, a hole injection layer (HIL) material is formed on the anode surface by vacuum thermal evaporation or spin coating using a conventional method. Such hole injection layer materials include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenyl) Amino)phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris Examples include (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu.

A hole transport layer is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating with a hole transport layer material using a conventional method.

A hole transport auxiliary layer is formed by vacuum thermal evaporation or spin coating with the compound represented by Formula 1 according to the present invention on the surface of the hole transport layer.

An emitting layer (EML) material is formed on the surface of the hole transport auxiliary layer by vacuum thermal evaporation or spin coating using a conventional method. At this time, among the light-emitting layer materials used, the sole light-emitting material or light-emitting host material may be tris(8-hydroxyquinolinolato)aluminum (Alq3) for green, and Alq3 or CBP(4,4' for blue). -N,N'-dicabazole-biphenyl, 4,4'-N,N'-dicabazole -biphenyl), PVK (poly(n-vinylcabazole), poly (n-vinylcarbazole)), ADN (9, 10-di(naphthalene-2-yl)anthracene, 9,10-di(naphthalene-2-yl)anthracene), TCTA, TPBI(1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene, 1 ,3,5-tris(N-phenylbenzimidazol-2-yl)benzene), TBADN(3-tert-butyl-9,10-di(naphth-2-yl) anthracene, 3-tert-butyl-9 , 10-di(naphth-2yl)anthracene), E3, DSA (distyrylarylene), or a mixture of two or more thereof may be used, but is not limited thereto.

Among the light-emitting layer materials, dopant that can be used with the light-emitting host is IDE102 and IDE105 available from Idemitsu, and the phosphorescent dopant is tris(2-phenylpyridine)iridium(III) ( Ir(ppy)3), iridium(III)bis[(4,6-difluorophenyl)pyridinato-N,C-2']picolinate (FIrpic) (see Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084], platinum (II) octaethylporphyrin (PtOEP), TBE002 (Covion), etc.

An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal evaporation or spin coating using a conventional method. At this time, the electron transport layer material used is not particularly limited, and tris(8-hydroxyquinolinolato)aluminum (Alq ₃ ) can be preferably used.

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer, diffusion of triplet excitons or holes into the electron transport layer can be prevented. .

The formation of the hole blocking layer can be performed by vacuum thermal evaporation and spin coating of the hole blocking layer material by conventional methods. The hole blocking layer material is not particularly limited, but is preferably (8-hydroxyquinolinola) To) Lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), and LiF can be used.

An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal evaporation or spin coating using a conventional method. At this time, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used as the electron injection layer material.

A cathode is formed by vacuum thermal deposition of a cathode material on the surface of the electron injection layer using a conventional method.

At this time, the cathode materials used include lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver. (Mg-Ag) etc. may be used. Additionally, in the case of a top-emitting organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) can be used to form a transparent cathode through which light can transmit.

A capping layer (CPL) may be formed on the surface of the cathode using a capping layer forming composition.

Hereinafter, methods for synthesizing the above compounds will be described with representative examples. However, the method of synthesizing the compounds of the present invention is not limited to the methods exemplified below, and the compounds of the present invention can be prepared by the methods exemplified below and methods known in the art.

[Synthesis example]

<Synthesis Example 1: Synthesis of Compound 1-41>

Synthesis Example 1-1: Synthesis of Intermediate 1-1

Dissolve 20 g (92 mmol) of 1-bromoadamantane in 32.9 g (139 mmol) of 1,3-dibromobenzene in a nitrogen atmosphere. 0.04 g (3 mmol) of aluminum chloride was slowly added and stirred at 60 degrees for 24 hours. The organic layer was extracted using water and dichloromethane, dried over MgSO4, and concentrated. It was purified by column chromatography with heptane. By reverse precipitation in methanol, 9.3 g (27%) of 1-(3,5-dibromophenyl)adamantane (Compound 1-1) was obtained.

Synthesis Example 1-2: Synthesis of Compound 1-41

Add 6.6 g (18 mmol) of compound 1-1, 13.7 g (43 mmol) of di([1,1'-biphenyl]-4-yl)amine, and 8.6 g (89 mmol) of sodium-tert butoxide and dissolve in 50 mL of toluene. and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.65 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.88 g (2 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated to 100-110°C. It was refluxed for 12 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain 6.8 g (45%) of compound 1-41.

<Synthesis Example 2: Synthesis of Compound 1-23>

Synthesis Example 2-1: Synthesis of Intermediate 2-1

20 g (81 mmol) of aniline, 9.1 g (97 mmol) of 3-bromobenzofuran, and 23.3 g (243 mmol) of sodium-tert-butoxide were added, dissolved in 150 mL of toluene, and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 1.5 g (2 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 1.7 g (4 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated to 100-110°C. It was refluxed for 5 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 300 mL of water and 200 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane. 18.1 g (86%) of N-phenyldibenzofuran-3-amine (Compound 2-1) was obtained.

Synthesis Example: 2-2: Synthesis of Compound 1-23

Add 6.3 g (17 mmol) of 1-(3,5-dibromophenyl)adamantane, 10.6 g (41 mmol) of N-phenyldibenzofuran-3-amine, and 8.2 g (85 mmol) of sodium-tert butoxide. It was dissolved in 50 mL of toluene and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.6 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.8 g (2 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated to 100-110°C. It was refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain 5.1 g (41%) of Compound 1-23.

<Synthesis Example 3: Synthesis of Compound 1-51>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-([1,1'-biphenyl]-4-yl)-[1, 6.4 g of compound 1-51 was obtained in 55.5% yield by preparing in the same manner as compound 1-41, except that 10.4 g (32 mmol) of 1'-biphenyl]-2-amine was used.

<Synthesis Example 4: Synthesis of Compound 1-15>

Instead of 5.0 g (14 mmol) of compound 1-1 and di([1,1'-biphenyl]-4-yl)amine, 9.7 g of 9,9-dimethyl-N-phenyl-9H-fluoren-1-amine ( It was prepared in the same manner as Compound 1-41 except that 34 mmol) was used, and 6.8 g of Compound 1-15 was obtained in 62.4% yield.

<Synthesis Example 5: Synthesis of Compound 1-112>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-([1,1'-biphenyl]-4-yl)dibenzo[b ,d]furan-3-amine was prepared in the same manner as compound 1-41 except that 11.4 g (34 mmol) was used, and 7.3 g of compound 1-112 was obtained in 59.3% yield.

<Synthesis Example 6: Synthesis of Compound 1-130>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-(9,9-dimethyl-9H-fluoren-2-yl)-9- It was prepared in the same manner as compound 1-41, except that 14.6 g (32 mmol) of phenyl-9H-carbazol-2-amine was used, and 6.7 g of compound 1-130 was obtained in 44.8% yield.

<Synthesis Example 7: Synthesis of Compound 1-131>

Instead of 5.0 g (14 mmol) of compound 1-1 and di([1,1'-biphenyl]-4-yl)amine, 14.8 g of 9,9-dimethyl-N-phenyl-9H-fluoren-3-amine ( 32 mmol) was prepared in the same manner as Compound 1-41, and 4.3 g of Compound 1-131 was obtained with a yield of 41.2%.

<Synthesis Example 8: Synthesis of Compound 1-106>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-([1,1'-biphenyl]-4-yl)-[1, Prepared in the same manner as compound 1-41, except for using 10.8 g (32 mmol) of 1':3',1"-terphenyl]-4'-amine, 6.4 g of compound 1-106 was obtained in 47.4% yield. did.

<Synthesis Example 9: Synthesis of Compound 1-122>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-([1,1'-biphenyl]-2-yl)dibenzo[b ,d] 6.4 g of compound 1-122 was obtained in 52.1% yield by preparing in the same manner as compound 1-41, except that 11.4 g (32 mmol) of thiophen-2-amine was used.

<Synthesis Example 10: Synthesis of Compound 1-56>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-([1,1':4',1"-terphenyl]-4- 1) It was prepared in the same manner as compound 1-41 except that 12.0 g (32 mmol) of naphthalen-2-amine was used, and 6.4 g of compound 1-56 was obtained in 49.7% yield.

<Synthesis Example 11: Synthesis of Compound 1-55>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, 9,9-dimethyl-N-(naphthalen-1-yl)-9H-fluorene- It was prepared in the same manner as Compound 1-41 except that 10.9 g (32 mmol) of 2-amine was used, and 4.6 g of Compound 1-55 was obtained in 38.7% yield.

<Synthesis Example 12: Synthesis of Compound 1-125>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-(4-(dibenzofuran-4-yl)phenyl)-[1,1 It was prepared in the same manner as Compound 1-41 except that 13.3 g (32 mmol) of '-diphenyl]-2-amine was used, and 6.3 g of Compound 1-125 was obtained in 45.2% yield.

<Synthesis Example 13: Synthesis of Compound 1-145>

Instead of compound 1-1 5.0 g (14 mmol) and di([1,1'-biphenyl]-4-yl)amine, N,9,9-triphenyl-9H-fluorene-2-amine 13.1 g (32 mmol) was prepared in the same manner as Compound 1-41, and 6.8 g of Compound 1-145 was obtained in 49.3% yield.

<Synthesis Example 14: Synthesis of Compound 1-136>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzothiamine It was prepared in the same manner as compound 1-41, except that 12.7 g (32 mmol) of ophen-3-amine was used, and 6.0 g of compound 1-136 was obtained in 44.8% yield.

<Synthesis Example 15: Synthesis of Compound 1-132>

Synthesis Example 15-1: Synthesis of Intermediate 15-1

Add 16.2 g (50 mmol) of 4-bromo-N,N-diphenylaniline, 13.6 g (65 mmol) of 9,9-dimethyl-9H-fluoren-3-amine, and 14.4 g (150 mmol) of sodium-tert butoxide. It was dissolved in 200 mL of toluene and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.75 g (1 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 1.7 g (4 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated to 100-110°C. It was refluxed for 5 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 300 mL of water and 200 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain N1-(9,9-dimethyl-9H-fluoren-3-yl)-N4,N4-diphenylbenzene- 18.7 g (83%) of 1,4-diamine (Compound 15-1) was obtained.

Synthesis Example: 15-2: Synthesis of compound 1-132

Same as compound 1-41 except that 15.4 g (34 mmol) of compound 15-1 was used instead of 5.0 g (14 mmol) of compound 1-1 and di([1,1'-biphenyl]-4-yl)amine. Prepared using this method, 9.8 g of compound 1-132 was obtained in 62.8% yield.

<Synthesis Example 16: Synthesis of Compound 1-154>

Synthesis Example 16-1: Synthesis of Intermediate 16-1

Add 5.0 g (14 mmol) of compound 1-1, 4.3 g (14 mmol) of di([1,1'-biphenyl]-4-yl)amine, and 3.9 g (41 mmol) of sodium-tert butoxide and dissolve in 50 mL of toluene. and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.88 g (0.8 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the concentration was 100~110. It was refluxed at ℃ for 12 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain N-([1,1'-biphenyl]-4-yl)-N-(3-((3r, 5r,7r)-adamantane-1-yl)-5-bromophenyl)-[1,1'-biphenyl]-4-amine (Compound 16-1) 9.0 g (67%) was obtained.

Synthesis Example: 16-2: Synthesis of compound 1-154

Compound 16-1 9.0 g (15 mmol) and N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine 5.6 g (15 mmol) and sodium-tert-butox 4.3 g (44 mmol) of side was added, dissolved in 50 mL of toluene, and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.9 g (0.9 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the solution reached 100~110. It was refluxed at ℃ for 12 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane. 7.9 g (58.1%) of compound 1-154 was obtained.

<Synthesis Example 17: Synthesis of Compound 1-156>

Compound 16-1 9.0 g (14 mmol) and N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine instead of N-phenyl-[1,1 ',2',1"-terphenyl]-4'-amine was prepared in the same manner as compound 1-154 except that 4.7 g (14 mmol) was used, and 5.9 g of compound 1-156 was obtained in 47.1% yield. .

<Synthesis Example 18: Synthesis of Compound 1-160>

Compound 16-1 9.0 g (14 mmol) and N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine instead of N-(4-(naphthalene- Compound 1-160 was prepared in the same manner as Compound 1-154, except that 6.5 g (14 mmol) of 2-yl)phenyl)spiro[cyclopentane-1,9'-fluorene]-2'-amine was used. 6.1 g was obtained in 42.8% yield.

<Synthesis Example 19: Synthesis of Compound 1-157>

Synthesis Example 19-1: Synthesis of Intermediate 19-1

Add 20 g (81 mmol) of aniline, 31.3 g (97 mmol) of 9-(3-bromophenyl)-9H-carbazole, and 23.3 g (243 mmol) of sodium-tert-butoxide, dissolve in 150 mL of toluene, and dissolve for 60 mL in a nitrogen atmosphere. It was maintained at ℃ for 30 minutes. After adding 1.5 g (2 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 1.7 g (4 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated to 100-110°C. It was refluxed for 5 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 300 mL of water and 200 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated and purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain 3-(9H-carbazol-9-yl)-N-phenylaniline (Compound 19-1) 23 g (85) %) was obtained.

Synthesis Example: 19-2: Synthesis of compound 1-157

Instead of 9.0 g (14 mmol) of Compound 16-1 and N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine, 4.7 g (14 mmol) of Compound 19-1 mmol) was prepared in the same manner as Compound 1-154, and 6.4 g of Compound 1-157 was obtained in 53.2% yield.

<Synthesis Example 20: Synthesis of Compound 1-154>

Instead of 9.0 g (14 mmol) of compound 16-1 and N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine, 3.5 g (21 mmol) of carbazole It was prepared in the same manner as Compound 1-154 except that it was used, and 6.2 g of Compound 1-154 was obtained in 63.6% yield.

<Synthesis Example 21: Synthesis of Compound 1-7>

Instead of 5.0 g (14 mmol) of compound 1-1 and di([1,1'-biphenyl]-4-yl)amine, 9.5 g (32 mmol) of 4-(naphthalen-1-yl)-N-phenylaniline was used. Except for this, it was prepared in the same manner as Compound 1-41, and 7.1 g of Compound 1-7 was obtained in 63.2% yield.

<Synthesis Example 22: Synthesis of Compound 1-12>

Compound 1-1, except that instead of 5.0 g (14 mmol) and di([1,1'-biphenyl]-4-yl)amine, 8.0 g (32 mmol) of 4-cyclohexyl-N-phenylaniline was used. Prepared in the same manner as 1-41, 5.5 g of compound 1-12 was obtained with a yield of 55.7%.

<Synthesis Example 23: Synthesis of Compound 1-36>

Instead of 5.0 g (14 mmol) of compound 1-1 and di([1,1'-biphenyl]-4-yl)amine, 8.7 g of N-(p-tolyl)dibenzo[b,d]furan-2-amine It was prepared in the same manner as Compound 1-41 except that (32 mmol) was used, and 6.9 g of Compound 1-36 was obtained in 65.1% yield.

<Synthesis Example 24: Synthesis of Compound 1-197>

Compound 1-1, except that 6.7 g (32 mmol) of N-phenylbenzofuran-2-amine was used instead of 5.0 g (14 mmol) and di([1,1'-biphenyl]-4-yl)amine. Prepared in the same manner as 1-41, 6.3 g of compound 1-197 was obtained with a yield of 71.9%.

<Synthesis Example 25: Synthesis of Compound 1-183>

Except that instead of 5.0 g (14 mmol) of Compound 1-1 and di([1,1'-biphenyl]-4-yl)amine, 6.3 g (32 mmol) of 3,5-dimethyl-N-phenylaniline was used. Prepared in the same manner as Compound 1-41, 6.2 g of Compound 1-183 was obtained with a yield of 73.3%.

<Synthesis Example 26: Synthesis of Compound 1-547>

Compound 1-1 5.0 g (14 mmol) and instead of di([1,1'-biphenyl]-4-yl)amine, N-([1,1'-biphenyl]-4-yl)-3,5 -Dimethyl-[1,1'-biphenyl]-4-amine was prepared in the same manner as compound 1-41 except that 11.2 g (32 mmol) was used, and 7.8 g of compound 1-547 was obtained in 61.7% yield. .

<Synthesis Example 27: Synthesis of Compound 1-548>

Except that instead of 5.0 g (14 mmol) of compound 1-1 and di([1,1'-biphenyl]-4-yl)amine, 8.1 g (32 mmol) of N,5-diphenylthiophen-2-amine was used. Then, it was prepared in the same manner as compound 1-41, and 6.9 g of compound 1-548 was obtained with a yield of 68.9%.

<Synthesis Example 28: Synthesis of Compound 1-549>

Synthesis Example 28-1: Synthesis of Compound 28-1

Add 10 g (27 mmol) of compound 1-1, 7.6 g (27 mmol) of bis(4-(tert-butyl)phenyl)amine, and 7.8 g (81 mmol) of sodium-tert-butoxide, dissolve in 100 mL of toluene, and dissolve for 60 minutes in a nitrogen atmosphere. It was maintained at ℃ for 30 minutes. After adding 0.5 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.58 g (1 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene to toluene, It was refluxed at 110°C for 8 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 200 mL of dichloromethane. After drying with MgSO, the filtrate was concentrated and purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain 3-((3r,5r,7r)-adamantane-1-yl)-5-bromo-N,N -Bis(4-(tert-butyl)phenyl)anilyl (Compound 28-1) 10.5 g (68%) was obtained.

Synthesis Example: 28-2: Synthesis of compound 1-549

Add 10.0 g (17.5 mmol) of compound 28-1, 5.4 g (19.3 mmol) of bis(3-(tert-butyl)phenyl)amine, and 5.1 g (52.5 mmol) of sodium-tert-butoxide, dissolve in 100 mL of toluene, and dissolve in 100 mL of toluene. It was maintained at 60°C for 30 minutes in an atmosphere. Add 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.5 g (0.9 mmol) of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl to toluene. Afterwards, it was refluxed at 100-110°C for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and the organic layer was extracted using 200 mL of water and 200 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane. 8.6 g (65.8%) of compound 1-549 was obtained.

<Synthesis Example 29: Synthesis of Compound 1-230>

Synthesis Example 29-1: Synthesis of Intermediate 29-1

Add 10.0 g (27 mmol) of compound 1-1, 7.7 g (27 mmol) of 9,9-dimethyl-N-phenyl-9H-fluoren-1-amine, and 7.8 g (81 mmol) of sodium-tert butoxide to 100 mL of toluene. It was dissolved and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.5 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.41 g (1 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated at 100-110°C. It was refluxed for 8 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated and purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain N-(3-((3r,5r,7r)-adamantan-1-yl)-5-bromo 10.0 g (65%) of phenyl)-9,9-dimethyl-N-phenyl-9H-fluoren-1-amine (Compound 29-1) was obtained.

Synthesis Example: 29-2: Synthesis of compound 1-230

10.0 g (17.4 mmol) of compound 29-1, 3.3 g (19.3 mmol) of diphenylamine, and 5.1 g (52.5 mmol) of sodium-tert-butoxide were added, dissolved in 100 mL of toluene, and maintained at 60°C for 30 minutes in a nitrogen atmosphere. . After adding 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.4 g (0.9 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the solution reached 100~110. It was refluxed at ℃ for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and the organic layer was extracted using 200 mL of water and 200 mL of dichloromethane. After drying with MgSO4, the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane. 7.1 g (61.6%) of compound 1-230 was obtained.

<Synthesis Example 30: Synthesis of Compound 1-402>

Synthesis Example 30-1: Synthesis of Intermediate 30-1

Add 10.0 g (27 mmol) of compound 1-1, 7.7 g (27 mmol) of N-phenyldibenzo[b,d]thiophen-4-amine, and 7.4 g (81 mmol) of sodium-tert butoxide and dissolve in 100 mL of toluene. It was maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.5 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.41 g (1 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated at 100-110°C. It was refluxed for 8 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated and purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain N-(3-((3r,5r,7r)-adamantan-1-yl)-5-bromo 10.2 g (67%) of phenyl)-N-phenyldibenzo[b,d]thiophen-4-amine (Compound 30-1) was obtained.

Synthesis Example: 30-2: Synthesis of compound 1-402

Add 10.0 g (17.7 mmol) of compound 30-1, 6.1 g (21.2 mmol) of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, and 5.1 g (53.1 mmol) of sodium-tert butoxide. It was dissolved in 100 mL of toluene and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.4 g (0.9 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the solution reached 100~110. It was refluxed at ℃ for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and the organic layer was extracted using 200 mL of water and 200 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane. 8.5 g (62.2%) of compound 1-402 was obtained.

<Synthesis Example 31: Synthesis of Compound 1-552>

Synthesis Example 31-1: Synthesis of Compound 31-1

Add 10.0 g (27 mmol) of compound 1-1, 7.0 g (27 mmol) of N-phenyldibenzo[b,d]furan-3-amine, and 7.4 g (81 mmol) of sodium-tert butoxide, dissolve in 100 mL of toluene, and dissolve in 100 mL of toluene. It was maintained at 60°C for 30 minutes in an atmosphere. After adding 0.5 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.41 g (1 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated at 100-110°C. It was refluxed for 8 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated and purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain N-(3-((3r,5r,7r)-adamantan-1-yl)-5-bromo 10.0 g (68%) of phenyl)-N-phenyldibenzo[b,d]furan-3-amine (Compound 31-1) was obtained.

Synthesis Example: 31-2: Synthesis of compound 1-552

10.0 g (18.2 mmol) of compound 31-1, 3.4 g (20.0 mmol) of diphenylamine, and 5.3 g (54.6 mmol) of sodium-tert-butoxide were added, dissolved in 100 mL of toluene, and maintained at 60°C for 30 minutes in a nitrogen atmosphere. . After adding 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.4 g (0.9 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the solution reached 100~110. It was refluxed at ℃ for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and the organic layer was extracted using 200 mL of water and 200 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane. 7.1 g (61.7%) of compound 1-552 was obtained.

<Synthesis Example 32: Synthesis of Compound 1-553>

Synthesis Example 32-1: Synthesis of Compound 32-1

Add 10.0 g (27 mmol) of compound 1-1, 10.8 g (27 mmol) of bis(9,9-dimethyl-9H-fluoren-2-yl)amine, and 7.4 g (81 mmol) of sodium-tert butoxide to 100 mL of toluene. It was dissolved in and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.5 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.41 g (1 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated at 100-110°C. It was refluxed for 8 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated and purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain N-(3-((3r,5r,7r)-adamantan-1-yl)-5-bromo Phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine (Compound 32-1) 11.4 g (61%) got it

Synthesis Example: 32-2: Synthesis of compound 1-553

10.0 g (14.5 mmol) of compound 31-1, 2.7 g (16.0 mmol) of diphenylamine, and 4.2 g (43.5 mmol) of sodium-tert butoxide were added, dissolved in 100 mL of toluene, and maintained at 60°C for 30 minutes in a nitrogen atmosphere. . After adding 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.4 g (0.9 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the solution reached 100~110. It was refluxed at ℃ for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and the organic layer was extracted using 200 mL of water and 200 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane. 7.1 g (63.2%) of compound 1-553 was obtained.

<Synthesis Example 33: Synthesis of Compound 1-554>

Synthesis Example 33-1: Synthesis of Compound 33-1

Add 10.0 g (27 mmol) of compound 1-1, 7.7 g (27 mmol) of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, and 7.4 g (81 mmol) of sodium-tert butoxide to 100 mL of toluene. It was dissolved in and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.5 g (0.5 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.41 g (1 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the mixture was heated at 100-110°C. It was refluxed for 8 hours. After completion of the reaction, it was cooled to room temperature and the organic layer was extracted using 200 mL of water and 100 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated and purified by column chromatography, and recrystallized with heptane/dichloromethane to obtain N-(3-((3r,5r,7r)-adamantan-1-yl)-5-bromo 10.2 g (66%) of phenyl)-9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (Compound 33-1) was obtained.

Synthesis Example: 33-2: Synthesis of compound 1-554

10.0 g (17.4 mmol) of compound 32-1, 4.7 g (19.1 mmol) of N-phenyl-[1,1'-biphenyl]-4-amine, and 5.0 g (52.2 mmol) of sodium-tert butoxide were added to toluene. It was dissolved in 100 mL and maintained at 60°C for 30 minutes in a nitrogen atmosphere. After adding 0.3 g (0.3 mmol) of tris(dibenzylideneacetone)dipalladium (0) and 0.4 g (0.9 mmol) of 2-dichlorohexylphosphine-2',6'-dimethoxybiphenyl to toluene, the solution reached 100~110. It was refluxed at ℃ for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and the organic layer was extracted using 200 mL of water and 200 mL of dichloromethane. After drying with MgSO ₄ , the filtrate was concentrated, purified by column chromatography, and recrystallized with heptane/dichloromethane. 8.3 g (64.2%) of compound 1-554 was obtained.

[Example 1: Manufacturing organic electroluminescent device (red)]

An anode was formed with ITO on the substrate with a reflective layer, and the surface was treated with N ₂ plasma or UV-ozone. On top of this, HAT-CN was deposited to a thickness of 10 nm as a hole injection layer (HIL). Next, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine was deposited to a thickness of 100 nm to form a hole transport layer. (HTL) was formed.

Compound 1-41 of the present invention was vacuum deposited to a thickness of 85 nm on the top of the hole transport layer to form a hole transport auxiliary layer, and 4,4'-N,N'-dicarbazole was added as an emitting layer (EML) on top of the hole transport auxiliary layer. While -biphenyl (CBP) was deposited at 35 nm, about 3% of (piq)2Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] was doped as a dopant.

An electron transport layer (ETL) was deposited to a thickness of 30 nm by mixing anthracene derivative and LiQ in a 1:1 ratio, and LiQ was deposited to a thickness of 1 nm as an electron injection layer (EIL) on top of this. Afterwards, a 1:4 mixture of magnesium and silver (Ag) was deposited to a thickness of 16 nm as a cathode, and N4,N4'-bis[4-[bis( 3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD)

It was deposited to a thickness of 60 nm. An organic electroluminescent device was manufactured by attaching a seal cap containing a moisture absorbent to the top using a UV curing adhesive to protect the organic electroluminescent device from atmospheric O2 or moisture.

[Examples 2 to 33]

Organic electroluminescent devices of Examples 2 to 33 and Comparative Examples 1 and 2 were manufactured in the same manner as Example 1, except that the hole transport auxiliary layer compound was used as shown in Table 1 below.

[Compound A]

[Compound B]

Hole transport auxiliary layer Example 1 Compound 1-41 Example 2 Compound 1-23 Example 3 Compound 1-51 Example 4 Compound 1-16 Example 5 Compound 1-112 Example 6 Compound 1-130 Example 7 Compound 1-131 Example 8 Compound 1-106 Example 9 Compound 1-122 Example 10 Compound 1-56 Example 11 Compound 1-55 Example 12 Compound 1-125 Example 13 Compound 1-145 Example 14 Compound 1-136 Example 15 Compound 1-132 Example 16 Compound 1-154 Example 17 Compound 1-156 Example 18 Compound 1-160 Example 19 Compound 1-157 Example 20 Compound 1-153 Example 21 Compound 1-7 Example 22 Compound 1-12 Example 23 Compound 1-36 Example 24 Compound 1-197 Example 25 Compound 1-183 Example 26 Compound 1-547 Example 27 Compound 1-548 Example 28 Compound 1-549 Example 29 Compound 1-261 Example 30 Compound 1-402 Example 31 Compound 1-552 Example 32 Compound 1-553 Example 33 Compound 1-554 Comparative Example 1 Compound A Comparative Example 2 Compound B

[Experimental Example 1: Device performance analysis]

For the organic electroluminescent devices manufactured in the Examples and Comparative Examples above, the electroluminescent characteristics when driven at a current of 10 mA/cm ² and the 95% reduction lifespan when driven at a constant current of 20 mA/cm ² were measured, and the results are shown in Table 2. shown in

Hole transport auxiliary layer Driving voltage (V) efficiency color life span Cd/A Im/A EQE CIEx CIey T95(hrs) Example 1 Compound 1-41 4.49 39.3 27.5 32.1 0.684 0.316 1000 Example 2 Compound 1-23 4.53 39.5 27.4 29.9 0.681 0.319 750 Example 3 Compound 1-51 4.45 39.9 28.1 30.9 0.681 0.319 900 Example 4 Compound 1-16 4.52 39.2 27.2 31.0 0.682 0.318 650 Example 5 Compound 1-112 4.54 39.5 27.3 31.3 0.682 0.318 750 Example 6 Compound 1-130 4.57 41.9 28.8 33.7 0.683 0.317 750 Example 7 Compound 1-131 4.46 41.6 29.3 36.7 0.690 0.310 660 Example 8 Compound 1-106 4.70 40.5 27.0 31.8 0.682 0.318 700 Example 9 Compound 1-122 4.68 36.9 24.7 27.6 0.679 0.321 900 Example 10 Compound 1-56 4.50 36.6 25.5 27.5 0.678 0.322 650 Example 11 Compound 1-55 4.51 40.7 28.4 30.5 0.680 0.320 700 Example 12 Compound 1-125 4.67 37.7 25.3 30.6 0.682 0.317 800 Example 13 Compound 1-145 4.88 38.6 24.8 30.3 0.682 0.318 850 Example 14 Compound 1-136 4.59 37.6 25.8 28.6 0.679 0.321 1000 Example 15 Compound 1-132 4.66 37.4 25.2 29.9 0.682 0.318 750 Example 16 Compound 1-154 4.39 36.6 26.2 29.2 0.681 0.319 750 Example 17 Compound 1-156 4.40 37.6 26.9 30.0 0.682 0.318 700 Example 18 Compound 1-160 4.30 38.6 23.1 30.3 0.682 0.318 700 Example 19 Compound 1-157 4.77 40.2 26.5 31.7 0.682 0.318 800 Example 20 Compound 1-153 4.48 40.2 28.2 31.4 0.682 0.318 800 Example 21 Compound 1-7 4.55 39.2 27.0 31.0 0.682 0.317 700 Example 22 Compound 1-12 4.67 38.9 26.2 30.6 0.682 0.318 900 Example 23 Compound 1-36 4.75 38.7 25.6 31.5 0.684 0.316 800 Example 24 Compound 1-197 4.23 39.4 29.3 31.4 0.682 0.318 900 Example 25 Compound 1-183 4.33 36.9 26.7 37.1 0.693 0.307 780 Example 26 Compound 1-547 4.44 40.9 28.9 36.8 0.688 0.312 750 Example 27 Compound 1-548 4.33 40.9 29.7 33.6 0.684 0.316 700 Example 28 Compound 1-549 4.25 37.9 28.0 32.2 0.685 0.315 870 Example 29 Compound 1-261 4.46 41.6 29.3 36.7 0.690 0.310 800 Example 30 Compound 1-402 4.51 29.8 20.7 31.9 0.688 0.312 800 Example 31 Compound 1-552 4.45 40.9 28.9 38.5 0.693 0.308 840 Example 32 Compound 1-553 4.65 34.3 23.2 32.8 0.670 0.328 750 Example 33 Example 1-554 4.49 42.1 29.4 36.7 0.688 0.312 850 Comparative Example 1 Compound A 4.50 29.9 20.9 27.2 0.677 0.321 470 Comparative Example 2 Compound B 4.66 34.6 23.3 26.9 0.673 0.327 460

According to the experimental results in Table 2, compared to the comparative example, when the compound of the present invention was used as a hole transport auxiliary layer material of an organic electroluminescent device, the driving voltage was at the same or lower level, but device efficiency and longer lifespan were lower. It was confirmed that the characteristics were exhibited.

[Example 34: Manufacturing organic electroluminescent device (green)]

An anode was formed with ITO on the substrate with a reflective layer, and the surface was treated with N2 plasma or UV-ozone. On top of this, HAT-CN was deposited to a thickness of 10 nm as a hole injection layer (HIL). Next, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine was deposited to a thickness of 110 nm to form a hole transport layer. (HTL) was formed.

Compound 1-41 of the present invention was vacuum deposited to a thickness of 40 nm on the top of the hole transport layer to form a hole transport auxiliary layer, and 4,4'-N,N'-dicarbazole was added as an emitting layer (EML) on top of the hole transport auxiliary layer. While -biphenyl (CBP) was deposited at 35 nm, approximately 5% of Ir(ppy)3[tris(2-phenylpyridine)-iridium] was doped as a dopant.

An electron transport layer (ETL) was deposited to a thickness of 30 nm by mixing anthracene derivative and LiQ in a 1:1 ratio, and LiQ was deposited to a thickness of 1 nm as an electron injection layer (EIL) on top of this. Afterwards, a 1:4 mixture of magnesium and silver (Ag) was deposited to a thickness of 16 nm as a cathode, and N4,N4'-bis[4-[bis( 3-Methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 60 nm. An organic electroluminescent device was manufactured by bonding a seal cap containing a moisture absorbent to the top using a UV curable adhesive to protect the organic electroluminescent device from atmospheric O2 or moisture.

[Examples 34 to 43]

Organic electroluminescent devices of Examples 34 to 43 and Comparative Examples 5 and 6 were manufactured in the same manner as Example 31, except that the hole transport auxiliary layer compound was used as shown in Table 3 below.

Hole transport auxiliary layer Example 34 Compound 1-41 Example 35 Compound 1-23 Example 36 Compound 1-553 Example 37 Compound 1-554 Example 38 Compound 1-112 Example 39 Compound 1-130 Example 40 Compound 1-131 Example 41 Compound 1-106 Example 42 Compound 1-122 Example 43 Compound 1-56 Comparative Example 3 Compound A Comparative Example 4 Compound B

[Experimental Example 2: Device performance analysis]

For the organic electroluminescent devices manufactured in Examples 34 to 43 and Comparative Examples 3 and 4 above, electroluminescent characteristics when driven at a current of 10 mA/cm ² and lifespan reduced by 95% when driven at a constant current of 20 mA/cm 2 was measured and shown in Table 4.

Hole transport auxiliary layer Driving voltage (V) efficiency color life span Cd/A Im/A EQE CIEx CIey T95(hrs) Example 34 Compound 1-41 3.80 126.9 105.0 30.3 0.242 0.718 296 Example 35 Compound 1-23 3.80 86.6 71.6 22.0 0.207 0.729 220 Example 36 Compound 1-553 3.97 104.8 82.9 26.2 0.216 0.730 250 Example 37 Example 1-554 3.93 104.4 83.5 26.1 0.217 0.726 246 Example 38 Compound 1-112 3.88 129.8 105.1 30.9 0.242 0.718 280 Example 39 Compound 1-130 4.12 102.0 77.8 25.4 0.220 0.725 255 Example 40 Compound 1-131 3.85 144.3 117.7 34.2 0.248 0.714 215 Example 41 Compound 1-106 3.88 141.3 114.5 33.6 0.248 0.714 190 Example 42 Compound 1-122 3.99 109.6 86.4 27.1 0.216 0.730 237 Example 43 Compound 1-56 3.89 124.1 100.1 29.6 0.242 0.718 287 Comparative Example 3 Compound A 4.10 121.3 92.9 29.0 0.239 0.720 185 Comparative Example 4 Compound B 3.98 111.0 87.7 27.0 0.233 0.721 188

According to the experimental results in Table 4 above, compared to the comparative example, when the compound of the present invention was used as a hole transport auxiliary layer material of an organic electroluminescent device, the driving voltage was at the same or lower level, but device efficiency and long life were lower. It was confirmed that the characteristics were exhibited.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims are also possible. falls within the scope of rights.

Claims (7)

Compound represented by Formula 1:
[Formula 1]

here,
n, m and p are the same or different from each other and are each independently an integer from 0 to 5,
Ring A, ring B, and ring C are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 5 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 60 nuclear atoms,
X ₁ and X ₂ are the same or different from each other and are each independently selected from the group consisting of N, O and S,
R ₁ to R ₅ are the same or different from each other, and each independently represents hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms. 30 alkyl group, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted alkyl group with 7 to 30 carbon atoms Alkyl group, substituted or unsubstituted aryl group with 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 5 to 60 nuclear atoms, substituted or unsubstituted heteroarylalkyl group with 6 to 30 carbon atoms, substituted or unsubstituted carbon number of 1 to 30 an alkoxy group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkylamino group having 2 to 24 carbon atoms. selected from the group consisting of a heteroarylamino group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and adjacent Groups can be combined with each other to form a substituted or unsubstituted ring,
At least one of R ₁ to R ₅ is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 30 carbon atoms. According to paragraph 1,
The compound represented by Formula 1 is a compound represented by Formula 2:
[Formula 2]

here,
n, m, X ₁ , X ₂ , R ₁ , R ₂ , R ₃ and R ₅ are as defined in clause 1,
q is an integer from 0 to 4,
R ₆ is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 5 to 30 carbon atoms. According to paragraph 1,
The A ring and the B ring are the same or different from each other, and are each independently selected from the group consisting of substituents having the following formulas 3 to 9:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

here,
* refers to the part that is combined,
r is an integer from 0 to 5,
s is an integer from 0 to 7,
t, v and a are the same or different from each other and are each independently an integer from 0 to 3,
u is an integer from 0 to 6,
w, x, y and z are the same or different from each other and are each independently an integer from 0 to 4,
X ₃ , X ₅ and _{and ​ ​ ​}
X ₄ is selected from the group consisting of a single bond, O, S, N(R ₂₀ ) and C(R ₂₁ )(R ₂₂ ),
X ₆ is selected from the group consisting of N(R ₂₃ ), O and S,
R ₇ to R ₂₃ are the same or different from each other, and each independently represents hydrogen, deuterium, cyano group, nitro group, halogen group, hydroxy group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms. 30 alkyl group, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted alkyl group with 7 to 30 carbon atoms Alkyl group, substituted or unsubstituted aryl group with 5 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 5 to 60 nuclear atoms, substituted or unsubstituted heteroarylalkyl group with 6 to 30 carbon atoms, substituted or unsubstituted carbon number of 1 to 30 an alkoxy group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkylamino group having 2 to 24 carbon atoms. selected from the group consisting of a heteroarylamino group, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and adjacent Groups can be combined with each other to form a substituted or unsubstituted ring. According to paragraph 1,
A compound wherein X ₁ and X ₂ are N. first electrode; a second electrode opposite the first electrode; It includes one or more organic layers interposed between the first electrode and the second electrode,
The one or more organic layers include one or more compounds according to claim 1.
Organic electroluminescent device. According to clause 5,
The organic material layer is selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a capping layer.
Organic electroluminescent device. According to clause 5,
The organic layer is a hole transport auxiliary layer.
Organic electroluminescent device.