KR20230013624A - Organic compound and organoelectroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic light emitting device including the same, and more particularly, provides an organic light emitting device having significantly improved low driving voltage, device efficiency characteristics and lifespan. An object of the present invention is to provide the organic electroluminescent device having a low driving voltage, excellent device efficiency and lifespan characteristics by including the novel organic compound.

Description

Organic compound and organic electroluminescent device containing the same {Organic compound and organoelectroluminescent device using the same}

The present invention relates to an organic compound and an organic light emitting device including the organic compound.

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

In an organic light emitting device, when a voltage is applied, holes injected from an anode and electrons injected from a cathode recombine to form excitons, which are electron-hole pairs.

In order to improve the efficiency and stability of the organic electroluminescent device, a low-voltage organic electroluminescent device comprising a layered organic thin film between two opposite electrodes was reported by C. W. Tang of Eastman Kodak Co., Ltd. (C. W. Tang, S. A. Vanslyke, Applied Physics Letters , Vol. 51, page 913, 1987), research on organic materials for multi-layer thin-film organic light emitting devices has been actively conducted.

In general, an organic light emitting 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 is 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. In order to increase the efficiency of the light emitting layer, an electron blocking layer (EBL) or a hole blocking layer (HBL) is added in front and behind the light emitting layer, respectively. can include

The reason why the organic light emitting device is manufactured in a multi-layered thin film structure is to stabilize the interface between the electrode and the organic material and to increase the luminous efficiency.

In particular, in the case of organic compounds used as materials for multilayer thin films, since the difference in the movement speed of holes and electrons is large depending on their characteristics, holes and electrons can be effectively transferred to the light emitting layer only when hole transport layers and electron transport layers containing appropriate compounds are used. And, the density of holes and electrons can be balanced to increase the luminous efficiency excellently.

For this reason, the characteristics of the organic compound components included in each layer of the organic thin film layer not only greatly affect the driving voltage, luminous efficiency, luminance, and lifespan of the device, but also affect the efficiency or lifespan of the finally produced display. Therefore, it is considered important to use a specific organic material suitable for a multilayer structure in an organic light emitting device. Therefore, research on components included in each layer of the organic thin film layer is being actively conducted.

(Patent Document 1) KR 10-2014-0133572 A1 (Patent Document 2) KR 10-1663355 B1

An object of the present invention is to provide an organic light emitting device including a novel organic compound having a low driving voltage and excellent device efficiency and lifespan characteristics.

In order to achieve the above object, the present invention may relate to a compound represented by Formula 1 or Formula 2 below:

[Formula 1]

[Formula 2]

here,

at least one of m or o is an integer from 2 to 4;

at least one of s or t is an integer from 2 to 4;

m, o, s, and t, which are not integers of 2 to 4, are the same as or different from each other, and are each independently an integer of 0 to 4,

n, p, r and u are the same as or different from each other, and each independently represents an integer from 0 to 4;

q and v are the same as or different from each other, and each independently represents an integer from 0 to 2;

R ₁ to R ₁₀ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or a substituted or unsubstituted carbon number. Alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted Aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl group having 2 to 30 carbon atoms, substituted Or an unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms Amino group, substituted or unsubstituted heteroarylamino group having 1 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted carbon atoms It is selected from the group consisting of 6 to 30 aryloxy groups, and may combine with adjacent groups to form a substituted or unsubstituted ring.

In addition, the present invention is a first electrode; a second electrode facing the first electrode; An organic electroluminescent device including one or more organic material layers interposed between the first electrode and the second electrode, wherein the one or more organic material layers include the compound represented by Chemical Formula 1.

In the present invention, "hydrogen" is hydrogen, light hydrogen, deuterium or tritium unless otherwise specified.

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

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

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

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

In the present invention, "alkylthio" means the above-described alkyl group bonded through a sulfur linkage (-S-).

In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in a single ring or a combination of two or more rings. In addition, a form in which two or more rings are simply pendant or condensed may be included, and specifically, a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, phenalenyl group, perylenyl group, cryenyl group It may be a cenyl group, a fluorenyl group, etc., but is not limited thereto. The fluorenyl group may be substituted, and adjacent groups may bond to each other to form a ring.

In the present invention, “heteroaryl” means 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 in the ring is substituted with a heteroatom such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and furthermore, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl and the like, but are not limited thereto.

In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means an aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

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

In the present invention, “alkoxy” may be straight chain, branched chain or cyclic chain. The number of carbon atoms in 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, but is not limited thereto.

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

In the present invention, "arylamino group" means 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, “aralkylamino group” means an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

In the present invention, "heteroarylamino group" means an amine group substituted with an aryl group having 6 to 30 carbon atoms and a heterocyclic group.

In the present invention, "heteroaralkyl group" means an aryl-alkyl group substituted with a heterocyclic group.

In the present invention, “cycloalkyl” means 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, adamantine, and the like.

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

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, "to form a ring by bonding with adjacent groups" means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; or to form a condensed ring thereof.

Examples of the “aromatic hydrocarbon ring” in the present invention include, but are not limited to, a phenyl group, a naphthyl group, an anthracenyl group, and the like.

In the present invention, "aliphatic heterocycle" means an aliphatic ring containing one or more of heteroatoms.

In the present invention, "aromatic heterocycle" means an aromatic ring containing one or more of heteroatoms.

In the present invention, "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other. The substituent is hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, and a C6 to C30 alkenyl group. 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 30 carbon atoms An arylamino group having 30 carbon atoms, an aralkylamino group having 6 to 30 carbon atoms, a hetero arylamino group having 2 to 24 carbon atoms, 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 it may be substituted with one or more substituents selected from the group consisting of an unsubstituted aryloxy group having 6 to 30 carbon atoms, but is not limited to the above examples.

The present invention is a novel organic compound, and when used as a material for an organic light emitting device, it may have excellent interfacial properties with adjacent layers and excellent chemical stability.

In addition, the present invention can provide an organic light emitting device having a low driving voltage and excellent device efficiency and lifespan characteristics, including the novel organic compound.

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

The novel organic compound according to the present invention has excellent interfacial properties with adjacent layers, can have excellent chemical stability, and has a HOMO energy level that facilitates hole transport, so that hole transport to the light emitting layer is excellent. Organic electroluminescent device It can be used as a hole transport auxiliary layer material.

Specifically, the compound represented by Formula 1 or Formula 2 is as follows:

[Formula 1]

[Formula 2]

here,

at least one of m or o is an integer from 2 to 4;

at least one of s or t is an integer from 2 to 4;

m, o, s, and t, which are not integers of 2 to 4, are the same as or different from each other, and are each independently an integer of 0 to 4,

n, p, r and u are the same as or different from each other, and each independently represents an integer from 0 to 4;

q and v are the same as or different from each other, and each independently represents an integer from 0 to 2;

R ₁ to R ₁₀ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or a substituted or unsubstituted carbon number. Alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted Aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl group having 2 to 30 carbon atoms, substituted Or an unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms Amino group, substituted or unsubstituted heteroarylamino group having 1 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted carbon atoms It is selected from the group consisting of 6 to 30 aryloxy groups, and may combine with adjacent groups to form a substituted or unsubstituted ring.

The compound represented by Formula 1 may be a compound represented by Formula 3 below:

[Formula 3]

here,

n, m, p, q, R ₁ , R ₂ , R ₄ and R ₅ are as defined in Formula 1 above;

L ₁ and L ₂ are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 1 to 30 carbon atoms. 10 alkylene group, substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms substituted or unsubstituted 1 carbon atom to 10 heteroalkylene groups, substituted or unsubstituted heterocycloalkylene groups having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkenylene groups having 2 to 10 carbon atoms, and substituted or unsubstituted heterocycloalkenylene groups having 2 to 10 carbon atoms. is selected from the group consisting of

Ar ₁ to Ar ₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. , A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms , It may be selected from the group consisting of a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 2 to 20 carbon atoms.

The compound represented by Formula 2 may be a compound represented by Formula 4 below:

[Formula 4]

here,

r, s, u, v, R ₆ , R ₇ , R ₉ and R ₁₀ are as defined in Formula 2 above;

L ₃ and L ₄ are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 1 to 30 carbon atoms. 10 alkylene group, substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms substituted or unsubstituted 1 carbon atom to 10 heteroalkylene groups, substituted or unsubstituted heterocycloalkylene groups having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkenylene groups having 2 to 10 carbon atoms, and substituted or unsubstituted heterocycloalkenylene groups having 2 to 10 carbon atoms. is selected from the group consisting of

Ar ₅ to Ar ₈ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. , A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms It is selected from the group consisting of a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 2 to 20 carbon atoms,

L ₁ to L ₄ are the same as or different from each other, and may be independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, and , preferably a single bond, and the amine group may be directly bonded to the benzene ring compound.

Ar ₁ to Ar ₈ are the same as or different from each other, and may each independently be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms.

The Ar ₁ to Ar ₈ are the same as or different from each other, and may be each independently selected from the group consisting of Chemical Formulas 5 to 9:

[Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

[Formula 9]

here,

* means a bonding part,

w is an integer from 0 to 5;

x is an integer from 0 to 7;

y is an integer from 0 to 6;

z, a and b are the same as or different from each other, and each independently represents an integer from 0 to 4;

X ₁ is selected from the group consisting of C(R ₁₇ )(R ₁₈ ), N(R ₁₉ ), O and S;

R ₁₁ to R ₁₉ are hydrogen, heavy hydrogen, cyano group, nitro group, halogen group, hydroxyl group, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted Cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted Or an unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms. Alkoxy group, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, substituted or unsubstituted 1 carbon atom to 24 heteroarylamino groups, substituted or unsubstituted alkylsilyl groups having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms, and substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms It is selected from, and may combine with adjacent groups to form a substituted or unsubstituted ring.

The compound represented by Formula 1 or Formula 2 according to the present invention is selected from the group consisting of the following compounds, but is not limited thereto:

The compound represented by Chemical Formula 1 or Chemical Formula 2 of the present invention may be usefully used as a hole transport auxiliary layer material.

When the organic compound is used as a material for an organic light emitting device, it may exhibit equal or superior properties in most device characteristics such as luminous efficiency and lifespan.

The present invention provides an organic electroluminescent device including the compound represented by Formula 1 or Formula 2 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 is an organic electroluminescent device in which an organic thin film layer comprising one or a plurality of 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 layer between the first electrode and the light emitting layer and/or or a hole transport auxiliary layer.

The hole transport layer and/or the hole transport auxiliary layer is a compound represented by Formula 1 or Formula 2 above.

The hole transport auxiliary layer reduces the accumulation of holes at the interface between the hole transport auxiliary layer and the light emitting layer by adjusting the hole injection characteristics by reducing the HOMO energy level difference between the hole transport layer and the light emitting layer, thereby reducing the polaron at the interface. quenching, in which excitons are quenched by Accordingly, deterioration of the device is reduced and the device is stabilized, thereby improving efficiency and lifetime.

The organic light emitting 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. If necessary, an electron transport auxiliary layer may be further added. can be layered.

Hereinafter, the organic electroluminescent device of the present invention will be described as an example. However, the content exemplified below does not limit the organic electroluminescent device of the present invention.

The organic light emitting 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, a light emitting layer (EML), and a cathode (electron injection electrode) are sequentially stacked. It may have, preferably, a hole transport auxiliary layer between the anode and the light emitting layer, and may further include an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the light emitting layer. In addition, an electron transport auxiliary layer may be further included between the cathode and the light emitting layer.

In the manufacturing method of the organic light emitting device according to the present invention, first, an anode is formed by coating a substrate surface with a material for an anode in a conventional manner. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and water resistance. In addition, as the material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, may be used.

Next, a hole injection layer (HIL) material is vacuum thermally deposited or spin-coated on the surface of the anode in a conventional manner to form a hole injection layer. Materials for the hole injection layer include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), and 4,4',4"-tris(3-methylphenyl). Amino) phenoxybenzene (m-MTDAPB), starburst amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris (N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu is exemplified.

A hole transport layer is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating using a conventional method. A hole transport layer material that is generally used may be used as the hole transport layer material.

A hole transport auxiliary layer may be formed by vacuum thermal evaporation or spin coating of the compound represented by Formula 1 or Formula 2 according to the present invention on the surface of the hole transport layer. As described above, the hole transport auxiliary layer may use the compound according to the present invention as a hole transport auxiliary layer material, and the hole transport auxiliary layer may be formed using a commonly used hole transport auxiliary layer material.

A light-emitting layer (EML) material is vacuum thermally deposited or spin-coated on the surface of the hole transport auxiliary layer in a conventional manner to form a light-emitting layer. At this time, as a single light emitting material or light emitting host material among the materials of the light emitting layer used, tris (8-hydroxyquinolinolato) aluminum (Alq3) may be used in the case of green, and Alq3, CBP (4,4') in the case of blue. -N,N'-dicabazole-biphenyl, 4,4'-N,N'-dicarbazole-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, distyrylarylene), or a mixture of two or more thereof may be used, but is not limited thereto.

In the case of a dopant that can be used with a light emitting host among the light emitting layer materials, IDE102 and IDE105 available from Idemitsu, and tris (2-phenylpyridine) iridium (III) as a phosphorescent dopant (Dopant) Ir(ppy)3), iridium(III)bis[(4,6-difluorophenyl)pyridinato-N,C-2']picolinate (FIrpic) (Chihaya Adachi et al., Phys.

An electron transport layer (ETL) material is vacuum thermally deposited or spin-coated on the surface of the light emitting layer in a conventional manner to form an electron transport layer. At this time, the electron transport layer material used is not particularly limited, and preferably tris(8-hydroxyquinolinolato) aluminum (Alq ₃ ) may be 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 together, diffusion of triplet excitons or holes into the electron transport layer can be prevented. .

Formation of the hole blocking layer may be carried out by vacuum thermal evaporation and spin coating of the hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, it is not particularly limited, but preferably (8-hydroxyquinolinola To) lithium (Liq), bis(8-hydroxy-2-methylquinolinato)-aluminum biphenoxide (BAlq), bathocuproine (BCP), LiF, and the like can be used.

An electron injection layer (EIL) material is vacuum thermally deposited or spin-coated on the surface of the electron transport layer in a conventional manner to form an electron injection layer. In this case, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used as the material for the electron injection layer.

An anode is formed by vacuum thermally depositing a cathode material on the surface of the electron injection layer in a conventional manner.

At this time, the negative electrode material used is lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) and the like may be used. In addition, in the case of a top emission organic light emitting device, a transparent cathode through which light can pass may be formed using indium tin oxide (ITO) or indium zinc oxide (IZO).

A capping layer CPL may be formed on a surface of the negative electrode using a composition for forming a capping layer.

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

1. Synthesis of Compound 1

1) Synthesis Example of Compound 1-1

2,4-dichloro-1-iodobenzene (50.0 g, 183.2 mmol), (2-bromophenyl)boronic acid (38.6 g, 192.4 mmol), K ₂ CO ₃ (50.8 g) were added to a 2000 mL flask under a nitrogen stream. , 367.8 mmol), Pd(PPh ₃ ) ₄ (4.25 g, 3.68 mmol), toluene (500 mL), EtOH (200 mL) and H ₂ O (200 mL) were added and the mixture was stirred and refluxed. After completion of the reaction, the organic layer was extracted using toluene and water. The extracted solution was treated with MgSO ₄ to remove residual moisture, concentrated under reduced pressure, and then purified by column chromatography to obtain 40.4 g of Compound 1-1 (yield: 73%).

2) Synthesis Example of Compound 1-2

Compound 1-1 (20.0 g, 66.23 mmol) was dissolved in anhydrous THF (60 mL) in a dry flask and cooled to -78 °C. At this temperature, 29.1 mL of a 2.5M n-BuLi solution dissolved in hexane was slowly added dropwise, followed by stirring at -78°C for 1 hour. 10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-one (13.8 g, 66.23 mmol) was dissolved in anhydrous THF (30 mL), added dropwise at -78°C, and then reacted. The mixture was slowly warmed to room temperature. After the reaction was completed, NH ₄ Cl was quenched into a solution, and the organic layer was extracted using ethyl acetate and water. The extracted solution was treated with MgSO ₄ to remove residual moisture, concentrated under reduced pressure, and purified by column chromatography to obtain 17.7 g of Compound 1-2 (yield: 62%).

3) Synthesis of compound 1-3

After adding trifluoroacetic acid (150 mL) to compound 1-2 (17.0 g, 39.41 mmol), the mixture was refluxed at 80° C. for 4 hours. After completion of the reaction, the organic layer was extracted using dichloromethane and water. The extracted solution was treated with MgSO ₄ to remove residual moisture, concentrated under reduced pressure, and purified by column chromatography to obtain 13.5 g of Compound 1-3 (yield: 83%).

4) Synthesis of Compound 1

Compound 1-3 (10.0 g, 24.19 mmol), diphenylamine (9.01 g, 53.22 mmol), t-BuONa (9.30 g, 96.77 mmol), Pd2(dba)3 (0.89 g, 0.97 mmol), sphos (0.80 g, 1.94 mmol), and toluene (200 mL) were added, and the mixture was refluxed while stirring. After completion of the reaction, the organic layer was extracted using toluene and water. The extracted solution was treated with MgSO ₄ to remove residual moisture, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain 10.68 g of Compound 1 (yield: 65%).

MS[M+H]+ = 679.31

2. Synthesis of Compound 15

Compound 15 13.27 g (yield) was synthesized and purified according to the method for preparing Compound 1, except that N-phenyl-[1,1'-biphenyl]-4-amine (13.06 g, 53.22 mmol) was used instead of diphenylamine. : 66%) was obtained.

MS[M+H]+ = 831.39

3. Synthesis of Compound 17

11.72 g of compound 17 (yield: 52%) was synthesized and purified according to the method for preparing compound 1, except that 4-(naphthalen-2-yl)-N-phenylaniline (15.72 g, 53.22 mmol) was used instead of diphenylamine. ) was obtained.

MS[M+H]+ = 931.43

4. Synthesis Example of Compound 6

Compound 6 was synthesized and purified according to the method for preparing Compound 1, except that 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (15.19 g, 53.22 mmol) was used instead of diphenylamine to obtain 12.57 g of Compound 6 ( Yield: 57%) was obtained.

MS[M+H]+ = 911.44

5. Synthesis Example of Compound 8

10.81 g (yield: 52%) of compound 8 was obtained by synthesis and purification according to the method for preparing compound 1, except that N-phenylbenzofuran-3-amine (13.80 g, 53.22 mmol) was used instead of diphenylamine.

MS[M+H]+ = 859.35

6. Synthesis of Compound 252

Compound 252 was synthesized and purified according to the method for preparing Compound 1, except that bis(phenyl-d5)-amine (9.54 g, 53.22 mmol) was used instead of diphenylamine to obtain 8.46 g of Compound 252 (yield: 50%).

MS[M+H]+ = 699.45

7. Synthesis of Compound 256

Compound 256 was synthesized and purified according to the method for preparing Compound 1, except that N-(phenyl-d5)-[1,1'-biphenyl]-4-amine (13.33 g, 53.22 mmol) was used instead of diphenylamine. 12.21 g (yield: 60%) was obtained.

MS[M+H]+ = 841.43

8. Synthesis of Compound 53

Compound 1 was synthesized and purified by the method for preparing Compound 1, except that N-([1,1'-biphenyl]-4-yl)naphthalen-2-amine (15.72 g, 53.22 mmol) was used instead of diphenylamine. 53 12.39 g (yield: 55%) was obtained.

MS[M+H]+ = 931.42

9. Synthesis of Compound 24

Compound 24 14.75 g (yield) was synthesized and purified according to the method for preparing compound 1, except that di([1,1'-bisphenyl]-4-yl)amine (17.11 g, 53.22 mmol) was used instead of diphenylamine. : 62%) was obtained.

MS[M+H]+ = 983.44

10. Synthesis of Compound 26

Method for preparing compound 1 except using N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (19.77 g, 53.22 mmol) instead of diphenylamine 13.89 g (yield: 53%) of compound 26 was obtained through synthesis and purification.

MS[M+H]+ = 1083.46

11. Synthesis of Compound 57

Compound 57 was synthesized and purified according to the method for preparing Compound 1, except that N-(4-(dibenzofuran-2-yl)phenyl)naphthalen-2-amine (13.8 g, 53.22 mmol) was used instead of diphenylamine. 12.64 g (yield: 47%) was obtained.

MS[M+H]+ = 1111.42

12. Synthesis of Compound 44

Compound 44 was synthesized and purified according to the method for preparing Compound 1, except that bis(9,9-dimethyl-9H-fluoren-2-yl)amine (21.37 g, 53.22 mmol) was used instead of diphenylamine to obtain 13.83 g of Compound 44 ( Yield: 50%) was obtained.

MS[M+H]+ = 1143.55

13. Synthesis of Compound 48

12.07 g (yield: 48%) of Compound 48 was obtained by synthesis and purification according to the method for preparing Compound 1, except that bis(dibenzofuran-3-yl)amine (18.60 g, 53.22 mmol) was used instead of diphenylamine. .

MS[M+H]+ = 1039.35

14. Synthesis of Compound 38

Compound 38 10.79 g (yield) was synthesized and purified according to the method for preparing compound 1, except that N-(naphthalen-1-yl)dibenzothiophen-2-amine (17.32 g, 53.22 mmol) was used instead of diphenylamine. : 45%) was obtained.

MS[M+H]+ = 991.32

15. Synthesis of Compound 66

12.73 g (yield: 51%) of Compound 66 was obtained by synthesis and purification according to the method for preparing Compound 1, except that N-phenylbenzofuran-3-amine (18.39 g, 53.22 mmol) was used instead of diphenylamine.

MS[M+H]+ = 1031.44

16. Synthesis of Compound 153

1) Synthesis of Compound 153-1

5H-dibenzo[a,d][7]annulen-5-one instead of 10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-one (13.7 g, 66.23 mmol ) was synthesized and purified according to the method for preparing compound 1-2, except for using, to obtain 18.5 g of compound 153-1 (yield: 65%).

2) Synthesis of Compound 153-2

Except for using compound 153-1 (18.0 g, 43.76 mmol) instead of compound 1-2, compound 1-3 was synthesized and purified to obtain 15.3 g of compound 153-2 (yield: 85%).

3) Synthesis of Compound 153

Compound 153 11.33 g (yield: 11.33 g (yield: 60%) was obtained.

MS[M+H]+ = 777.33

17. Synthesis of Compound 166

Synthesized by the method for preparing compound 1 except using compound 153-2 (10.0 g, 24.31 mmol) and N-phenyl-[1,1'-biphenyl]-2-amine (13.12 g, 53.49 mmol), Purification gave 11.49 g of compound 166 (yield: 57%).

MS[M+H]+ = 829.36

18. Synthesis of Compound 221

Compound 1 except for using compound 153-2 (10.0 g, 24.31 mmol) and N-([1,1'-biphenyl]-4-yl)naphthalen-1-amine (15.80 g, 53.49 mmol) 12.42 g (yield: 55%) of compound 221 was obtained by synthesis and purification according to the manufacturing method.

MS[M+H]+ = 929.38

19. Synthesis of Compound 156

Synthesis of compound 1 except for using compound 153-2 (10.0 g, 24.31 mmol) and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (15.26 g, 53.49 mmol) , to obtain 14.15 g of compound 156 (yield: 64%).

MS[M+H]+ = 909.42

20. Synthesis of Compound 161

Compound 161 12.11 g ( Yield: 56%) was obtained.

MS[M+H]+ = 889.26

21. Synthesis of Compound 175

Synthesized by the method for preparing compound 1 except using compound 153-2 (10.0 g, 24.31 mmol) and di([1,1'-biphenyl]-4-yl)amine (17.19 g, 53.49 mmol), Purification gave 16.22 g of Compound 175 (yield: 68%).

MS[M+H]+ = 981.41

22. Synthesis of Compound 242

Compound except using compound 153-2 (10.0 g, 24.31 mmol) and N-([1,1'-biphenyl]-4-yl)dibenzofuran-3-amine (17.94 g, 53.49 mmol) 13.74 g (yield: 56%) of Compound 242 was obtained by synthesizing and purifying by the method of 1.

MS[M+H]+ = 1009.37

23. Synthesis of Compound 127

Except using compound 153-2 (10.0 g, 24.31 mmol) and N-(4-(naphthalen-1-yl)phenyl)-2-(naphthalen-2-yl)aniline (22.55 g, 53.49 mmol) It was synthesized and purified according to the method for preparing Compound 1 to obtain 14.94 g of Compound 127 (yield: 52%).

MS[M+H]+ = 1181.49

24. Synthesis of Compound 281

Preparation of compound 1 except using compound 153-2 (10.0 g, 24.31 mmol) and N-(phenyl-d5)-[1,1'-biphenyl]-4-amine (13.39 g, 53.49 mmol) 11.83 g (yield: 58%) of Compound 281 was obtained through synthesis and purification according to the method.

MS[M+H]+ = 839.43

25. Synthesis of Compound 187

Compound 1 was synthesized and purified except for using compound 153-2 (10.0 g, 24.31 mmol) and N-(naphthalen-2-yl)dibenzofuran-3-amine (16.55 g, 53.49 mmol). Thus, 12.10 g of Compound 187 (yield: 52%) was obtained.

MS[M+H]+ = 957.35

26. Synthesis of Compound 173

Synthesis and purification of Compound 1 except for using Compound 153-2 (10.0 g, 24.31 mmol) and 4-(dibenzofuran-4-yl)-N-phenylaniline (17.94 g, 53.49 mmol). Thus, 12.02 g (yield: 49%) of Compound 173 was obtained.

MS[M+H]+ = 1009.38

27. Synthesis of Compound 228

Compound 1 except using compound 153-2 (10.0 g, 24.31 mmol) and N-([1,1'-biphenyl]-4-yl)phenanthren-9-amine (18.48 g, 53.49 mmol) 13.51 g (yield: 54%) of compound 228 was obtained through synthesis and purification according to the method of preparation.

MS[M+H]+ = 1029.44

28. Synthesis of Compound 206

Except using compound 153-2 (10.0 g, 24.31 mmol) and N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzofuran-3-amine (20.08 g, 53.49 mmol) Compound 206 was synthesized and purified according to the method for preparing Compound 1, and 12.71 g (yield: 48%) was obtained.

MS[M+H]+ = 1089.43

29. Synthesis of Compound 212

Compound 1 was prepared by the method except for using compound 153-2 (10.0 g, 24.31 mmol) and N-(dibenzothiophen-2-yl)dibenzofuran-2-amine (19.55 g, 53.49 mmol). After synthesis and purification, 11.70 g of compound 212 (yield: 45%) was obtained.

MS[M+H]+ = 1069.29

30. Synthesis of Compound 172

Synthesis of compound 1 except for using compound 153-2 (10.0 g, 24.31 mmol) and 4-(dibenzothiophen-2-yl)-N-phenylaniline (18.80 g, 53.49 mmol), Purification gave 13.42 g of compound 172 (yield: 53%).

MS[M+H]+ = 1041.34

[Example 1-1: Manufacturing organic light emitting device]

An anode was formed with ITO on the substrate on which the reflective layer was formed, and the surface was treated with N2 plasma or UV-ozone. HAT-CN was deposited thereon to a thickness of 10 nm as a hole injection layer (HIL). Subsequently, 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 of the present invention was vacuum-deposited to a thickness of 85 nm on top of the hole transport layer to form a hole transport auxiliary layer, and 4,4'-N,N'-dicarbazole-biphenyl was formed as an emitting layer (EML) on the hole transport auxiliary layer. (CBP) was deposited at 35 nm, and (piq) ₂ Ir(acac) [bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] was doped by about 3% as a dopant.

Anthracene derivative and LiQ were mixed 1:1 thereon to deposit an electron transport layer (ETL) to a thickness of 30 nm, and LiQ was deposited thereon to a thickness of 1 nm as an electron injection layer (EIL). Thereafter, a mixture of magnesium and silver (Ag) in a ratio of 1:4 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 light emitting device was manufactured by bonding a seal cap containing a moisture absorbent with a UV curable adhesive thereon to protect the organic light emitting device from O2 or moisture in the air.

[Examples 1-2 to 1-20]

Compound 17, 6, 8, 256, 24, 26, 44, 48, 38, 153, 221, 156, 175, 242, 127, 187, 228 instead of the hole transport auxiliary layer in Example 1-1 , 206, 212 was prepared in the same manner as in Example 1 except for using an organic light emitting device.

[Comparative Examples 1-1 to 1-10]

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compounds A to J were used instead of Compound 1 as the hole transport auxiliary layer in Example 1-1.

[Compound A]

[Compound B]

[Compound C]

[Compound D]

[Compound E]

[Compound F]

[Compound G]

[Compound H]

[Compound I]

[Compound J]

[Experimental Example 1-1: Device performance analysis]

For the organic light emitting devices prepared in Examples and Comparative Examples above, the light emission characteristics when driven with a current of 10 mA/cm ² and the 95% reduced lifespan when driven with a constant current of 20 mA/cm 2 were measured and are shown in Table 1. showed up

division hole transport
auxiliary layer drive voltage efficiency color life span V Cd/A EQE CIEx CIEy T95 (hrs) Example
1-1 compound 1 4.10 40.4 27.6 0.670 0.330 800 Example 1-2 compound 17 4.39 35.0 27.2 0.677 0.323 750 Example 1-3 compound 6 4.39 34.9 28.2 0.677 0.323 850 Example 1-4 compound 8 4.44 33.0 26.8 0.678 0.322 700 Example 1-5 compound 256 4.51 40.8 29.1 0673 0.327 750 Example 1-6 compound 24 4.27 33.7 27.0 0.676 0.324 800 Example 1-7 compound 26 4.29 31.7 26.9 0.678 0.322 750 Example 1-8 compound 44 4.44 36.4 27.3 0.675 0.325 850 Example 1-9 compound 48 4.22 31.5 27.7 0.680 0.320 780 Example 1-10 compound 38 4.05 37.1 28.8 0.678 0.322 880 Example 1-11 compound 153 4.25 36.3 27.9 0.675 0.324 800 Example 1-12 compound 221 4.32 31.4 27.5 0.679 0.321 830 Example 1-13 compound 156 4.24 33.8 27.3 0.675 0.325 860 Examples 1-14 compound 175 4.09 32.1 27.4 0.677 0.322 900 Example 1-15 compound 242 4.04 33.2 25.3 0.674 0.326 850 Example 1-16 compound 127 4.34 32.2 26.5 0.675 0.325 820 Example 1-17 compound 187 3.99 34.8 25.7 0.671 0.329 770 Example 1-18 compound 228 4.33 32.5 25.5 0.678 0.322 850 Examples 1-19 compound 206 3.98 31.5 27.7 0.679 0.320 870 Example 1-20 compound 212 4.10 34.4 26.1 0.672 0.328 750 Comparative Example 1-1 compound A 4.89 24.0 24.5 0.669 0.331 480 Comparative Example 1-2 compound B 4.65 24.1 24.8 0.673 0.327 600 Comparative Example 1-3 compound C 4.85 24.8 24.7 0.673 0.327 500 Comparative Example 1-4 compound D 4.64 21.8 23.4 0.683 0.317 550 Comparative Example 1-5 compound E 4.62 21.4 22.8 0.683 0.317 530 Comparative Example 1-6 compound F 4.57 24.8 24.7 0.683 0.317 570 Comparative Example 1-7 compound G 4.69 26.1 24.2 0.679 0.321 520 Comparative Example 1-8 compound H 4.81 23.9 24.7 0.686 0.314 550 Comparative Example 1-9 compound I 4.93 26.1 23.2 0.680 0.320 480 Comparative Example 1-10 compound J 4.66 21.5 22.9 0.685 0.316 510

According to the experimental results of Table 1, compared to the comparative example, when the compound of the present invention is used as a hole transport auxiliary layer material of an organic electroluminescent device, the driving voltage is low, and exhibits excellent device efficiency characteristics and long lifespan characteristics. Confirmed.

[Example 2-1: Manufacturing organic light emitting device]

An anode was formed with ITO on the substrate on which the reflective layer was formed, and the surface was treated with N2 plasma or UV-ozone. HAT-CN was deposited thereon to a thickness of 10 nm as a hole injection layer (HIL). Subsequently, 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.

A hole transport auxiliary layer was formed by vacuum depositing the compound 15 of the present invention to a thickness of 40 nm on top of the hole transport layer, and 4,4'-N,N'-dicarbazole-biphenyl was formed as an emitting layer (EML) on the hole transport auxiliary layer. (CBP) was deposited at 35 nm, and about 5% of Ir(ppy) ₃ [tris(2-phenylpyridine)-iridium] was doped as a dopant.

Anthracene derivative and LiQ were mixed 1:1 thereon to deposit an electron transport layer (ETL) to a thickness of 30 nm, and LiQ was deposited thereon to a thickness of 1 nm as an electron injection layer (EIL). Then, a mixture of magnesium and silver (Ag) in a ratio of 1:4 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 light emitting device was manufactured by bonding a seal cap containing a moisture absorbent with a UV curable adhesive thereon to protect the organic light emitting device from O2 or moisture in the air.

[Examples 2-2 to 2-20]

Compound 6, 8, 252, 53, 24, 57, 44, 48, 66, 166, 156, 161, 175, 242, 281, 173, 206 instead of the hole transport auxiliary layer in Example 2-1 , 212, and 172 were prepared in the same manner as in Example 2-1, except that an organic light emitting device was prepared.

[Comparative Examples 2-1 to 2-10]

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compounds A to J were used instead of Compound 15 as the hole transport auxiliary layer in Example 2-1.

[Compound A]

[Compound B]

[Compound C]

[Compound D]

[Compound E]

[Compound F]

[Compound G]

[Compound H]

[Compound I]

[Compound J]

[Experimental Example 2-1: Device performance analysis]

For the organic light emitting device prepared in Examples and Comparative Examples above, the light emission characteristics when driven with a current of 10 mA/cm ² and the 95% reduced lifetime when driven with a constant current of 20 mA/cm ² were measured and Table 1 shown in

division hole transport
auxiliary layer driving voltage efficiency color life span V Cd/A EQE CIEx CIEy T95 (hrs) Example
2-1 compound 15 3.91 115.0 26.9 0.238 0.712 245 Example 2-2 compound 6 3.88 136.3 32.1 0.263 0.703 250 Example 2-3 compound 8 3.89 111.3 27.4 0.237 0.714 265 Example 2-4 compound 252 3.90 111.2 27.4 0.237 0.713 270 Example 2-5 compound 53 3.59 117.0 28.6 0.227 0.723 248 Example 2-6 compound 24 3.62 115.6 28.3 0.227 0.724 254 Example 2-7 compound 57 3.57 113.3 27.8 0.225 0.724 280 Examples 2-8 compound 44 3.56 113.6 27.8 0.226 0.724 275 Example 2-9 compound 48 3.49 130.9 30.9 0.258 0.706 265 Example 2-10 compound 66 3.56 123.3 29.3 0.251 0.710 290 Example 2-11 compound 166 3.52 118.8 28.1 0.256 0.707 250 Example 2-12 compound 156 3.55 118.0 28.4 0.239 0.718 255 Example 2-13 compound 161 3.78 128.9 31.2 0.242 0.713 240 Example 2-14 compound 175 4.00 127.6 30.9 0.243 0.713 235 Example 2-15 compound 242 3.91 135.7 32.7 0.245 0.713 225 Example 2-16 compound 281 3.98 135.5 32.3 0.259 0.703 255 Example 2-17 compound 173 4.00 137.1 32.5 0.271 0.696 267 Example 2-18 compound 206 3.93 143.3 34.1 0.249 0.712 265 Example 2-19 compound 212 3.99 115.7 28.5 0.231 0.719 280 Example 2-20 compound 172 3.92 141.9 33.5 0.253 0.711 260 Comparative Example 2-1 compound A 4.25 103.6 24.3 0.227 0.718 180 Comparative Example 2-2 compound B 4.23 98.0 23.0 0.229 0.715 185 Comparative Example 2-3 compound C 4.21 102.2 24.0 0.230 0.715 160 Comparative Example 2-4 compound D 4.25 73.7 18.4 0.222 0.721 190 Comparative Example 2-5 compound E 4.22 61.7 15.6 0.213 0.724 180 Comparative Example 2-6 compound F 4.28 83.5 20.5 0.228 0.721 175 Comparative Example 2-7 compound G 4.21 106.6 24.9 0.230 0.716 165 Comparative Example 2-8 compound H 4.25 106.1 24.7 0.239 0.711 180 Comparative Example 2-9 compound I 4.29 104.8 24.8 0.220 0.722 180 Comparative Example 2-10 compound J 4.26 105.8 25.2 0.224 0.722 170

According to the experimental results of Table 2, compared to the comparative example, when the compound of the present invention is used as a hole transport auxiliary layer material of an organic electroluminescent device, the driving voltage is low, and exhibits excellent device efficiency characteristics and long lifespan characteristics. Confirmed.

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 of those skilled in the art using the basic concept of the present invention defined in the following claims are also made according to the present invention. falls within the scope of the rights of

Claims (8)

represented by Formula 1 or Formula 2 below
compound:
[Formula 1]

[Formula 2]

here,
at least one of m or o is an integer from 2 to 4;
at least one of s or t is an integer from 2 to 4;
m, o, s, and t, which are not integers of 2 to 4, are the same as or different from each other, and are each independently an integer of 0 to 4,
n, p, r and u are the same as or different from each other, and each independently represents an integer from 0 to 4;
q and v are the same as or different from each other, and each independently represents an integer from 0 to 2;
R ₁ to R ₁₀ are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a cyano group, a nitro group, a halogen group, a hydroxy group, a substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, or a substituted or unsubstituted carbon number. Alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted Aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl group having 2 to 30 carbon atoms, substituted Or an unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms Amino group, substituted or unsubstituted heteroarylamino group having 1 to 24 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and substituted or unsubstituted carbon atoms It is selected from the group consisting of 6 to 30 aryloxy groups, and may combine with adjacent groups to form a substituted or unsubstituted ring. According to claim 1,
The compound represented by Formula 1 is represented by Formula 3 below:
compound:
[Formula 3]

here,
n, m, p, q, R ₁ , R ₂ , R ₄ and R ₅ are as defined in claim 1,
L ₁ and L ₂ are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 1 to 30 carbon atoms. 10 alkylene group, substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms substituted or unsubstituted 1 carbon atom to 10 heteroalkylene groups, substituted or unsubstituted heterocycloalkylene groups having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkenylene groups having 2 to 10 carbon atoms, and substituted or unsubstituted heterocycloalkenylene groups having 2 to 10 carbon atoms. is selected from the group consisting of
Ar ₁ to Ar ₄ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. , A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms , It may be selected from the group consisting of a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 2 to 20 carbon atoms. According to claim 1,
The compound represented by Formula 2 is represented by Formula 4 below:
compound:
[Formula 4]

here,
r, s, u, v, R ₆ , R ₇ , R ₉ and R ₁₀ are as defined in claim 1,
L ₃ and L ₄ are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 1 to 30 carbon atoms, or a substituted or unsubstituted arylene group having 1 to 30 carbon atoms. 10 alkylene group, substituted or unsubstituted cycloalkylene group having 3 to 10 carbon atoms, substituted or unsubstituted alkenylene group having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkenylene group having 3 to 10 carbon atoms substituted or unsubstituted 1 carbon atom to 10 heteroalkylene groups, substituted or unsubstituted heterocycloalkylene groups having 2 to 10 carbon atoms, substituted or unsubstituted heterocycloalkenylene groups having 2 to 10 carbon atoms, and substituted or unsubstituted heterocycloalkenylene groups having 2 to 10 carbon atoms. is selected from the group consisting of
Ar ₅ to Ar ₈ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. , A substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms , It may be selected from the group consisting of a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, and a substituted or unsubstituted heteroalkenyl group having 2 to 20 carbon atoms. According to claim 2 or 3,
Wherein L ₁ to L ₄ are the same as or different from each other, and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms. According to claim 2 or 3,
Wherein Ar ₁ to Ar ₈ are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 1 to 30 carbon atoms. a first electrode; a second electrode provided to face the first electrode; and one or more organic material layers provided between the first electrode and the second electrode,
An organic electroluminescent device in which at least one of the one or more organic material layers contains the compound according to claim 1. According to claim 6,
The organic material layer is an organic electroluminescent device selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light emitting layer, an electron transport layer, and an electron injection layer. According to claim 6,
The organic material layer is an organic electroluminescent device that is a hole transport auxiliary layer.