KR102559589B1 - Organic compound and organic electroluminescent device including the same - Google Patents

Abstract

The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, to a novel compound having excellent light emitting ability and characteristics such as high luminous efficiency, low driving voltage, and long lifespan by including the same in one or more organic material layers. It relates to an improved organic electroluminescent device.

Description

Organic compound and organic electroluminescent device containing the same {ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE INCLUDING THE SAME}

The present invention relates to a novel organic compound that can be used as a material for an organic electroluminescent device and an organic electroluminescent device including the same.

With the observation of organic thin film emission by Bernanose in the 1950s as a starting point, research on organic electroluminescent (EL) devices, which led to blue electroluminescence using anthracene single crystal in 1965, has been continued. In 1987, Tang presented an organic electroluminescent device with a laminated structure divided into a hole layer and a functional layer of a light emitting layer. Since then, in order to make a high-efficiency, long-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.

In the organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. At this time, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function.

Light-emitting materials may be classified into blue, green, and red light-emitting materials, and yellow and orange light-emitting materials required to realize better natural colors according to the light-emitting color. In addition, in order to increase color purity and increase light emitting efficiency through energy transfer, a host/dopant system may be used as a light emitting material.

The dopant material may be divided into a phosphorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the phosphorescent material can theoretically improve the luminous efficiency four times that of the fluorescent material, research on phosphorescent host materials as well as the phosphorescent dopant is being conducted.

Until now, NPB, BCP, Alq ₃ and the like have been widely known as materials for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as materials for the light emitting layer. In particular, phosphorescent materials having an advantage in terms of efficiency improvement among light emitting materials are blue, green, and red dopant materials such as Firpic, Ir(ppy) ₃ , (acac)Ir(btp) ₂ A metal complex compound containing Ir is used. Until now, 4,4-dicarbazolylbiphenyl (4,4-dicarbazolylbiphenyl, CBP) has shown excellent properties as a phosphorescent host material.

However, conventional materials are advantageous in terms of light emitting properties, but have poor thermal stability due to their low glass transition temperature, so they are not at a satisfactory level in terms of lifespan of organic light emitting devices. Therefore, the development of materials with higher performance is required.

An object of the present invention is to provide a novel organic compound capable of improving the bonding force between holes and electrons while having excellent thermal stability due to a high glass transition temperature.

In addition, an object of the present invention is to provide an organic electroluminescent device exhibiting a low driving voltage and high luminous efficiency and having an improved lifetime, including the novel organic compound.

In order to achieve the above object, an example of the present invention provides a compound represented by Formula 1 below.

In Formula 1,

X ₁ to X ₅ are the same as or different from each other, and each independently represents N or CR, provided that one of X ₁ to X ₅ is N;

A plurality of R's are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, C_One~C₄₀Alkyl group of, C₂~C₄₀of the alkenyl group, C₂~C₄₀of the alkynyl group, C₃~C₄₀A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C₆~C₆₀An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C_One~C₄₀Alkyloxy group of, C₆~C₆₀aryloxy group, C_One~C₄₀of the alkylsilyl group, C₆~C₆₀Of the arylsilyl group, C_One~C₄₀Alkyl boron group of, C₆~C₆₀aryl boron group, C₆~C₆₀Arylphosphine group of, C₆~C₆₀Of the arylphosphine oxide group and C₆~C₆₀It is selected from the group consisting of an arylamine group of,

Ar_One to Ar₂are the same as or different from each other, and each independently hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, C_One~C₄₀Alkyl group of, C₂~C₄₀of the alkenyl group, C₂~C₄₀of the alkynyl group, C₃~C₄₀A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C₆~C₆₀An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C_One~C₄₀Alkyloxy group of, C₆~C₆₀aryloxy group, C_One~C₄₀of the alkylsilyl group, C₆~C₆₀Of the arylsilyl group, C_One~C₄₀Alkyl boron group of, C₆~C₆₀aryl boron group, C₆~C₆₀Arylphosphine group of, C₆~C₆₀Of the aryl phosphine oxide group and C₆~C₆₀is selected from the group consisting of arylamine groups of, or they may form condensed rings with adjacent groups;

A is a substituent represented by Formula 2 below,

In Formula 2,

Y is O, S or CR ₃ R ₄ ;

n and m are each an integer from 0 to 4;

R_One to R₄are the same as or different from each other, and each independently hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, C_One~C₄₀Alkyl group of, C₂~C₄₀of the alkenyl group, C₂~C₄₀of the alkynyl group, C₃~C₄₀A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C₆~C₆₀An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C_One~C₄₀Alkyloxy group of, C₆~C₆₀aryloxy group, C_One~C₄₀of the alkylsilyl group, C₆~C₆₀Of the arylsilyl group, C_One~C₄₀Alkyl boron group of, C₆~C₆₀aryl boron group, C₆~C₆₀Arylphosphine group of, C₆~C₆₀Of the aryl phosphine oxide group and C₆~C₆₀is selected from the group consisting of arylamine groups of, or they may form condensed rings with adjacent groups;

However, any one of R ₁ to R ₄ is a single bond, which is bonded to Formula 1,

above Ar_One, Ar₂ and R_One to R₄Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group and arylamine group each independently deuterium, halogen, cyano group, nitro group, amino group, C₂~C₄₀of the alkenyl group, C₂~C₄₀of the alkynyl group, C₃~C₄₀A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C_One~C₄₀Alkyl group of, C₆~C₆₀An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C_One~C₄₀Alkyloxy group of, C₆~C₆₀aryloxy group, C_One~C₄₀of the alkylsilyl group, C₆~C₆₀Of the arylsilyl group, C_One~C₄₀Alkyl boron group of, C₆~C₆₀aryl boron group, C₆~C₆₀Arylphosphine group of, C₆~C₆₀Of the aryl phosphine oxide group and C₆~C₆₀substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and when the substituents are plural, they are the same as or different from each other.

In addition, the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes the compound represented by Formula 1. It provides an organic electroluminescent device.

Here, at least one of the one or more organic material layers including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron transport auxiliary layer, and an electron injection layer, and is preferably an electron transport layer, an electron transport auxiliary layer and/or a light emitting layer. In this case, the compound represented by Formula 1 is an electron transport layer material, an electron transport auxiliary layer material, and/or a light emitting layer material.

Since the compound represented by Chemical Formula 1 of the present invention has excellent thermal stability, carrier transport ability, luminescence, etc., it can be used as an organic material layer material of an organic electroluminescent device.

In addition, when the compound represented by Formula 1 according to an example of the present invention is used as a material for the organic layer, an organic electroluminescent device having greatly improved aspects such as excellent light emitting performance, driving voltage, lifetime, and efficiency can be manufactured, and furthermore, such an organic electroluminescent device can be effectively applied to a full color display panel or the like.

Hereinafter, the present invention will be described in detail.

1. Organic compounds

The novel organic compound according to the present invention is a compound having a structure in which a dibenzofuran, dibenzothiophene, or fluorene moiety and a divalent pyridine group are linked by a linker group between a fluorene moiety and an electron-withdrawing group (EWG) triazine as a basic skeleton, and is represented by Formula 1 above.

Specifically, in the compound represented by Chemical Formula 1, a dibenzofuran, dibenzothiophene, or fluorene moiety is introduced into a triazine moiety through a pyridine moiety. Here, when the dibenzofuran, dibenzothiophene, or fluorene moiety is bonded to a position immediately adjacent to the nitrogen of the pyridine moiety, that is, at an ortho position, hydrogen bonds are formed between the nitrogen of the pyridine group and the dibenzofuran, dibenzothiophene, or fluorene moiety, and between the nitrogen of the triazine and the dibenzofuran, dibenzothiophene, or fluorene moiety. These hydrogen bonds increase the thermal stability of molecules by making the intermolecular attraction stronger.

In the compound represented by Formula 1, since dibenzofuran, dibenzothiophene, or fluorene having high hole mobility is linked to a triazine having electron withdrawing characteristics through a divalent pyridine group, the intermolecular packing is better, resulting in excellent electron transport properties, as well as excellent thermal stability due to high triplet energy and high glass transition temperature. For this reason, since the compound represented by Chemical Formula 1 has excellent electron transport capability and light emitting characteristics, it can be used as a material for any one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, which are organic layers of an organic electroluminescent device. Preferably, the compound represented by Formula 1 may be used as a material for any one of the light emitting layer, the electron transport layer, and the electron transport auxiliary layer additionally stacked on the electron transport layer.

Specifically, since the compound represented by Chemical Formula 1 has high triplet energy, it can be used as a material for an electron transport auxiliary layer due to a triplet-triplet fusion (TTF) effect, thereby exhibiting an excellent increase in efficiency. In addition, diffusion of excitons generated in the light emitting layer to an electron transport layer or a hole transport layer adjacent to the light emitting layer can be prevented. The number of excitons contributing to light emission in the light emitting layer is increased so that the light emitting efficiency of the device can be improved, and the lifespan of the device can be effectively increased by improving durability and stability of the device. An organic electroluminescent device to which the compound represented by Chemical Formula 1 is applied can be driven at a low voltage, thereby exhibiting physical characteristics of improving lifespan.

Therefore, when the compound represented by Chemical Formula 1 is used in an organic electroluminescent device, excellent thermal stability, carrier transport ability (particularly, electron transport ability) and luminescent performance can be expected, as well as driving voltage, efficiency, lifespan, etc. of the device can be improved.

In addition, the compound represented by Chemical Formula 1 is very advantageous for electron transport and exhibits long lifespan characteristics. The excellent electron transport ability of these compounds can have high efficiency and fast mobility in organic electroluminescent devices, and HOMO and LUMO energy levels can be easily adjusted according to the direction or position of the substituent. Therefore, organic electroluminescent devices using these compounds can exhibit high electron transport properties.

In the compound represented by Formula 1, the X ₁ to X ₅ are CR or N. However, one of X ₁ to X ₅ is N.

A plurality of R's are the same as or different from each other, and each independently represents hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, C_One~C₄₀Alkyl group of, C₂~C₄₀of the alkenyl group, C₂~C₄₀of the alkynyl group, C₃~C₄₀A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C₆~C₆₀An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C_One~C₄₀Alkyloxy group of, C₆~C₆₀aryloxy group, C_One~C₄₀of the alkylsilyl group, C₆~C₆₀Of the arylsilyl group, C_One~C₄₀Alkyl boron group of, C₆~C₆₀aryl boron group, C₆~C₆₀Arylphosphine group of, C₆~C₆₀Of the aryl phosphine oxide group and C₆~C₆₀It is selected from the group consisting of an arylamine group.

above Ar_One and Ar₂are the same as or different from each other, and each independently hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, C_One~C₄₀Alkyl group of, C₂~C₄₀of the alkenyl group, C₂~C₄₀of the alkynyl group, C₃~C₄₀A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C₆~C₆₀An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C_One~C₄₀Alkyloxy group of, C₆~C₆₀aryloxy group, C_One~C₄₀of the alkylsilyl group, C₆~C₆₀Of the arylsilyl group, C_One~C₄₀Alkyl boron group of, C₆~C₆₀aryl boron group, C₆~C₆₀Arylphosphine group of, C₆~C₆₀Of the aryl phosphine oxide group and C₆~C₆₀is selected from the group consisting of arylamine groups, or they may form condensed rings with adjacent groups.

In Formula 2, Y is O, S or CR₃R₄And, wherein n and m are each an integer from 0 to 4, and the R_One to R₄are the same as or different from each other, and each independently hydrogen, heavy hydrogen, a halogen group, a cyano group, a nitro group, an amino group, C_One~C₄₀Alkyl group of, C₂~C₄₀of the alkenyl group, C₂~C₄₀of the alkynyl group, C₃~C₄₀A cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, C₆~C₆₀An aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C_One~C₄₀Alkyloxy group of, C₆~C₆₀aryloxy group, C_One~C₄₀of the alkylsilyl group, C₆~C₆₀Of the arylsilyl group, C_One~C₄₀Alkyl boron group of, C₆~C₆₀aryl boron group, C₆~C₆₀Arylphosphine group of, C₆~C₆₀Of the aryl phosphine oxide group and C₆~C₆₀is selected from the group consisting of arylamine groups, or they may form condensed rings with adjacent groups.

However, any one of R ₁ to R ₄ in Formula 2 is a single bond (direct bond), which is a site bonded to Formula 1. That is, the carbon bonded to any one of R ₁ to R ₄ in Formula 2 is connected to the carbon bonded to any one of multiple Rs in Formula 1, and in this case, the carbon in Formula 2 does not have a substituent.

According to one example, when Y is O or S in Formula 2, one or more of R ₁ and one or more of R ₂ is a single bond, which is a site bonded to Formula 1. For example, A represented by Formula 2 is a substituent represented by Formula 2a below.

[Formula 2a]

In Formula 2a,

Y is O or S;

R ₁ , R ₂ and m are each as defined in Formula 2, and n is an integer from 0 to 3.

According to another example, when Y is CR ₃ R ₄ in Formula 2, one or more of R ₁ , one or more of R ₂ , R ₃ and R ₄ is a single bond, which is bonded to Formula 1. For example, A represented by Formula 2 is a substituent represented by Formula 2b or Formula 2c below.

[Formula 2b]

In Formula 2b,

R ₁ , R ₂ , R ₄ , n and m are each as defined in Formula 2.

[Formula 2c]

In Formula 2c,

R ₁ , R ₂ , R ₃ , R ₄ and m are each as defined in Formula 2, provided that n is an integer from 0 to 3.

Specifically, the compound represented by Formula 1 may be represented by Formula 3 below.

In Formula 3,

X ₁ to X ₅ , Ar ₁ , Ar ₂ , Y, R ₁ and R ₂ are each as defined in Formula 1 above;

n and m are each an integer of 0 to 4, provided that 0≤n+m≤7.

In the compound represented by Formula 3, when Y is O, the dibenzofuran moiety may have a structure bonded to the triazine moiety through a divalent pyridine group, and when Y is S, the dibenzothiophene moiety may have a structure bonded to the triazine moiety through a divalent pyridine group, and when Y is CR ₃ R ₄ , the fluorene moiety is bonded to the triazine moiety through a divalent pyridine group may have a structure coupled to

Specifically, the compound represented by Formula 1 may be embodied in any one of Formulas 4 to 6 below.

In Formulas 4 to 6,

X ₁ to X ₅ , Ar ₁ , Ar ₂ , R ₃ and R ₄ are each as defined in Formula 1 above.

Preferably, the compound represented by Formula 1 includes a divalent pyridine group in which only one of X ₁ to X ₅ is N and the other is CR as a linking group, and is directly adjacent to nitrogen (N) of the linking group, the pyridine group. It may have a structure in which A is bonded to an ortho position.

Specifically, the compound represented by Formula 1 may be represented by any one of Formulas 7 to 10 below.

In Formulas 7 to 10,

Ar ₁ , Ar ₂ and A are each as defined in Formula 1 above.

Preferably, Ar ₁ and Ar ₂ are the same as or different from each other, and may be each independently selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

More preferably, Ar ₁ and Ar ₂ may be the same as or different from each other, and each independently may be a substituent selected from the group consisting of Structural Formulas S1 to S8 below.

In the above structural formula, * means a site bonded to Formula 1.

The compound represented by Formula 1 according to an example of the present invention described above may be further embodied as a compound represented by any one of Compounds 1 to 171 exemplified below. However, the compound represented by Formula 1 of the present invention is not limited to those exemplified below.

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 of such alkyl include, but are not limited to, methyl, ethyl, propyl, butyl, isobutyl, sec-butyl, pentyl, isoamyl, hexyl, and the like.

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 at least one carbon-carbon double bond. Examples of such alkenyl 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 of such alkynyl include, but are not limited to, ethynyl and 2-propynyl.

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, 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 nuclear atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

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 attached to each other (pendant) or condensed may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear 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 heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl. and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl and the like, but are not limited thereto.

In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R' means alkyl having 1 to 40 carbon atoms. Such alkyloxy may include a linear, branched or cyclic structure. Examples of such 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, "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, "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, "alkyl boron" refers to boron substituted with alkyl having 1 to 40 carbon atoms, and "aryl boron" refers to boron substituted with aryl having 6 to 60 carbon atoms.

In the present invention, "arylphosphine" means a phosphine substituted with aryl having 6 to 60 carbon atoms, and "arylphosphine oxide group" means that phosphine substituted with aryl having 6 to 60 carbon atoms includes O.

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, "arylamine" means an amine substituted with an aryl having 6 to 60 carbon atoms.

The compound represented by Chemical Formula 1 of the present invention can be variously synthesized by referring to the synthesis process in the following examples.

2. Organic electroluminescent device

The present invention relates to an organic electroluminescent device including the compound represented by Formula 1 above.

Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers includes a compound represented by Formula 1. At this time, the above compounds may be used alone or in combination of two or more.

According to one example, the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and at least one organic material layer among them may include a compound represented by Chemical Formula 1. Preferably, the organic material layer containing the compound of Formula 1 may be a light emitting layer and/or an electron transport layer, more preferably an electron transport layer. In addition, it is also preferable to include an electron transport auxiliary layer composed of the compound represented by Formula 1 between the electron transport layer and the light emitting layer.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, and may be, for example, a structure in which one layer or two or more organic material layers are stacked between electrodes. Non-limiting examples thereof include (i) an anode, a light emitting layer, and a cathode; (ii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode; (iii) an anode, a hole injection layer, a hole transport layer, a light emitting layer, and a cathode; or (iv) structures such as an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, an electron injection layer, and a cathode.

In addition, the organic electroluminescent device according to the present invention may have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked as described above, and an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic material layer.

The organic electroluminescent device according to the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except for forming at least one layer of the organic material layer to include the compound represented by Formula 1 of the present invention.

The organic material layer containing the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution application method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

Substrates usable in the present invention are not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; and carbon black, but is not limited thereto.

In addition, examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; and multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

In addition, the hole injection layer, the hole transport layer, the light emitting layer, the electron injection layer and the electron transport layer are not particularly limited, and conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail through examples. However, the following examples are only to illustrate the present invention, and the present invention is not limited by the following examples.

[Preparation Example 1] Synthesis of Core-1

<Step 1> Synthesis of (3-chloro-2-(dibenzo[b,d]furan-1-yl)pyridine

2,3-Dichloropyridine (14.8 g, 100 mmol), dibenzo[b,d]furan-1-ylboronic acid (21 g, 100 mmol), Pd(PPh ₃ ) ₄ (4.6 g, 4 mmol), and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 °C for 8 hours. After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO ₄ . After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain (3-chloro-2-(dibenzo[b,d]furan-1-yl)pyridine (25 g, yield 89%).

^1H -NMR: δ 7.19 (t, 1H), 7.32 (t, 1H), 7.38 (t, 1H), 7.47 (t, 1H), 7.58 (d, 1H), 7.66 (d, 1H), 7.68 (d, 1H), 7.89 (d, 1H), 8.26 (d, 1H), 8.59 (t, 1H)

<Step 2> Synthesis of Core-1

(3-chloro-2-(dibenzo[b,d]furan-1-yl)pyridine (25 g, 89 mmol), Pd(dppf)Cl ₂ (2.6 g, 4 mmol), Pinacol diboron (27 g, 107 mmol), and KOAc (26 g, 267 mmol) were added to 200 ml DMF and stirred at 110 °C for 8 hours. After the reaction was completed, H ₂ O was added. , The organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO _4. After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain Core-1 (29 g, yield 88%).

^1H -NMR: δ 1.24 (s, 12H), 7.00 (t, 1H), 7.32 (t, 1H), 7.38 (d, 2H), 7.47 (t, 1H), 7.66 (d, 1H), 7.68 (d, 1H), 7.89 (d, 1H), 8.26 (d, 1H), 8.50 (d, 1H)

[Preparation Example 2] Synthesis of Core-2

<Step 1> Synthesis of (3-chloro-2-(dibenzo[b,d]furan-2-yl)pyridine

2,3-Dichloropyridine (14.8 g, 100 mmol), dibenzo[b,d]furan-1-ylboronic acid (21 g, 100 mmol), Pd(PPh ₃ ) ₄ (4.6 g, 4 mmol), and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 °C for 8 hours. After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO ₄ . After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain (3-chloro-2-(dibenzo[b,d]furan-2-yl)pyridine (24 g, yield 86%).

^1H -NMR: δ 7.19 (t, 1H), 7.32 (t, 1H), 7.38 (t, 1H), 7.58 (d, 1H), 7.66 (d, 1H), 7.68 (d, 1H), 7.75 (d, 1H), 7.89 (d, 1H), 8.22 (s, 1H), 8.59 (t, 1H)

<Step 2> Synthesis of Core-2

(3-chloro-2-(dibenzo[b,d]furan-2-yl)pyridine (24 g, 86 mmol), Pd(dppf)Cl ₂ (2.5 g, 3 mmol), Pinacol diboron (26 g, 103 mmol), and KOAc (25 g, 257 mmol) were added to 200 ml DMF and stirred at 110 °C for 8 hours. After the reaction was completed, H ₂ O was added. , The organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO _4. After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain Core-2 (24 g, yield 75%).

^1H -NMR: δ 1.24 (s, 12H), 7.00 (t, 1H), 7.32 (t, 1H), 7.38 (d, 2H), 7.66 (d, 1H), 7.75 (d, 1H), 7.89 (d, 1H), 8.22 (s, 1H), 8.32 (d, 1H), 8.50 (d, 1H)

[Preparation Example 3] Synthesis of Core-3

<Step 1> Synthesis of (3-chloro-2-(dibenzo[b,d] furan-3-yl)pyridine

2,3-Dichloropyridine (14.8 g, 100 mmol), dibenzo[b,d]furan-3-ylboronic acid (21 g, 100 mmol), Pd(PPh ₃ ) ₄ (4.6 g, 4 mmol), and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 °C for 8 hours. After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO ₄ . After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain (3-chloro-2-(dibenzo[b,d]furan-3-yl)pyridine (25 g, yield 89%).

^1H -NMR: δ 7.19 (t, 1H), 7.32 (t, 1H), 7.38 (t, 1H), 7.58 (d, 1H), 7.66 (d, 1H), 7.89 (d, 1H), 7.98 (d, 1H), 8.15 (s, 1H), 8.26 (d, 1H), 8.59 (t, 1H)

<Step 2> Synthesis of Core-3

(3-chloro-2-(dibenzo[b,d]furan-3-yl)pyridine (25 g, 89 mmol), Pd(dppf)Cl ₂ (2.6 g, 4 mmol), Pinacol diboron (27 g, 107 mmol), and KOAc (26 g, 267 mmol) were added to 200 ml DMF and stirred at 110 °C for 8 hours. After the reaction was completed, H ₂ O was added. , The organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO _4. After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain Core-3 (29 g, yield 88%).

^1H -NMR: δ 1.24 (s, 12H), 7.00 (t, 1H), 7.32 (t, 1H), 7.38 (d, 2H), 7.66 (d, 1H), 7.89 (d, 1H), 7.98 (d, 1H), 8.15 (s, 1H), 8.26 (d, 1H), 8.50 (d, 1H)

[Preparation Example 4] Synthesis of Core-4

<Step 1> Synthesis of (3-chloro-2-(dibenzo[b,d]thiophen-1-yl)pyridine

2,3-Dichloropyridine (14.8 g, 100 mmol), dibenzo[b,d]thiophen-1-ylboronic acid (24 g, 100 mmol), Pd(PPh ₃ ) ₄ (4.6 g, 4 mmol), and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75 °C for 8 hours. After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO ₄ . After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain (3-chloro-2-(dibenzo[b,d]thiophen-1-yl)pyridine (28 g, yield 93%).

^1H -NMR: δ 7.19 (t, 1H), 7.50 (t, 1H), 7.52 (t, 1H), 7.58 (d, 1H), 7.59 (t, 1H), 7.98 (d, 1H), 8.00 (d, 1H), 8.33 (d, 1H), 8.45 (d, 1H), 8.59 (d, 1H)

<Step 2> Synthesis of Core-4

(3-chloro-2-(dibenzo[b,d]thiophen-1-yl)pyridine (28 g, 95 mmol), Pd(dppf)Cl ₂ (2.8 g, 4 mmol), Pinacol diboron (29 g, 114 mmol), and KOAc (28 g, 283 mmol) were added to 200 ml DMF and stirred at 110 °C for 8 hours. After the reaction was completed, H ₂ O was added. , The organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO _4. After removing the solvent from the water-free organic layer, it was purified by column chromatography to obtain Core-4 (35 g, yield 88%).

^1H -NMR: δ 1.24 (s, 12H), 7.00 (t, 1H), 7.38 (d, 1H), 7.50 (t, 1H), 7.52 (t, 1H), 7.59 (t, 1H), 7.98 (d, 1H), 8.00 (d, 1H), 8.33 (d, 1H), 8.45 (d, 1H), 8.50 (d, 1H)

[Preparation Example 5] Synthesis of Core-5

<Step 1> Synthesis of 3-chloro-2-(9,9-dimethyl-9H-fluoren-4-yl)pyridine

2,3-Dichloropyridine (14.8 g, 100 mmol), (9,9-dimethyl-9H-fluoren-4-yl)boronic acid (24 g, 100 mmol), Pd(PPh ₃ ) ₄ (4.6 g, 4 mmol), and NaOH (12 g, 300 mmol) were added to 500 ml THF and 200 ml H ₂ O and stirred at 75℃ for 8 hours. did After completion of the reaction, the organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO ₄ . After removing the solvent from the water-free organic layer, the mixture was purified by column chromatography to obtain 3-chloro-2-(9,9-dimethyl-9H-fluoren-4-yl)pyridine (28 g, yield 90%).

^1H -NMR: δ 1.72 (s, 6H), 7.19 (t, 1H), 7.28 (t, 1H), 7.37 (t, 1H), 7.38 (t, 1H), 7.55 (d, 1H), 7.57 (d, 1H), 7.58 (d, 1H), 7.87 (d, 1H), 8.14 (d, 1H), 8.59 (d, 1H)

<Step 2> Synthesis of Core-5

3-chloro-2-(9,9-dimethyl-9H-fluoren-4-yl)pyridine (28 g, 92 mmol), Pd(dppf)Cl ₂ (2.7 g, 4 mmol), Pinacol diboron (28 g, 110 mmol), and KOAc (27 g, 274 mmol) were added to 200 ml DMF and stirred at 110 °C for 8 hours. After completion of the reaction, H ₂ O was added, the organic layer was separated by extraction with ethyl acetate, and water was removed using MgSO ₄ . After removing the solvent from the organic layer from which water was removed, Core-5 (34 g, yield 96%) was obtained by purification using column chromatography.

^1H -NMR: δ 1.24 (s, 12H), 1.72 (s, 6H), 7.00 (t, 1H), 7.28 (t, 1H), 7.37 (t, 1H), 7.38 (t, 2H), 7.55 (d, 1H), 7.57 (d, 1H), 7.87 (d, 1H), 8.14 (d, 1H), 8.50 (d, 1H)

[Synthesis Example 1] Synthesis of Compound 2

Core-1 (5.0 g, 13.5 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (4.6 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were dissolved in 50 ml THF and 20 ml H ₂ O. Put and stirred at 75 ℃ for 8 hours. After the completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. And after concentrating toluene, it was recrystallized with toluene to obtain compound 2 (5 g, yield 67%).

[LCMS]: 552

[Synthesis Example 2] Synthesis of Compound 5

Core-1 (5.0 g, 13.5 mmol), 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (5.7 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were added to 50 ml THF and 20 ml H ₂ O. Stirred at 75° C. for 8 hours. After the completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. Then, after concentrating toluene, it was recrystallized from toluene to obtain compound 5 (6 g, yield 71%).

[LCMS]: 628

[Synthesis Example 3] Synthesis of Compound 7

Core-1 (5.0 g, 13.5 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (5.9 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were added to 50 It was put into ml THF and 20 ml H ₂ O and stirred at 75°C for 8 hours. After completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. And after concentrating toluene, it was recrystallized from toluene to obtain compound 7 (6.5 g, yield 76%).

[LCMS]: 642

[Synthesis Example 4] Synthesis of Compound 8

Core-1 (5.0 g, 13.5 mmol), 2-chloro-4,6-bis(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (6 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were added to 50 ml THF and 20 ml H ₂ O, followed by 7 Stirred for 8 hours at 5°C. After the completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. And after concentrating toluene, it was recrystallized from toluene to obtain compound 8 (7 g, yield 79%).

[LCMS]: 656

[Synthesis Example 5] Synthesis of Compound 25

Core-2 (5.0 g, 13.5 mmol 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (5.9 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were added to 50 ml T It was added to HF and 20 ml H ₂ O and stirred at 75 ° C. for 8 hours. After the reaction was completed, the resulting solid was dissolved in toluene and filtered through silica, and after concentrating toluene, it was recrystallized with toluene to obtain compound 25 (6.5 g, yield 76%).

[LCMS]: 642

[Synthesis Example 6] Synthesis of Compound 41

Core-3 (5.0 g, 13.5 mmol), 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (4.8 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were dissolved in 50 ml THF and 20 ml H ₂ O. Put and stirred at 75 ℃ for 8 hours. After the completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. And after concentrating toluene, it was recrystallized with toluene to obtain compound 41 (5.8 g, yield 76%).

[LCMS]: 566

[Synthesis Example 7] Synthesis of Compound 66

Core-4 (5.2 g, 13.5 mmol), 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine (5.7 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were added to 50 ml THF and 20 ml H ₂ O. Stirred at 75° C. for 8 hours. After the completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. Then, after concentrating toluene, it was recrystallized from toluene to obtain compound 66 (7.5 g, yield 86%).

[LCMS]: 644

[Synthesis Example 8] Synthesis of Compound 68

Core-4 (5.2 g, 13.5 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (5.9 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were added to 50 It was put into ml THF and 20 ml H ₂ O and stirred at 75°C for 8 hours. After completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. Then, after concentrating toluene, it was recrystallized from toluene to obtain compound 68 (7.6 g, yield 85%).

[LCMS]: 658

[Synthesis Example 9] Synthesis of Compound 71

Core-4 (5.2 g, 13.5 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-(dibenzo[b,d]thiophen-3-yl)-1,3,5-triazine (6.1 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were added to 50 It was put into ml THF and 20 ml H ₂ O and stirred at 75°C for 8 hours. After completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. And after concentrating toluene, it was recrystallized with toluene to obtain compound 71 (8.5 g, yield 93%).

[LCMS]: 674

[Synthesis Example 10] Synthesis of Compound 136

Core-5 (5.4 g, 13.5 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (4.6 g, 13.5 mmol) and Pd(PPh ₃ ) ₄ (0.6 g, 0.5 mmol), NaOH (1.6 g, 40 mmol) were dissolved in 50 ml THF and 20 ml H ₂ O. Put and stirred at 75 ℃ for 8 hours. After completion of the reaction, the produced solid was dissolved in toluene and filtered through silica after filtering. And after concentrating toluene, it was recrystallized with toluene to obtain compound 136 (5.5 g, yield 71%).

[LCMS]: 578

[Example 1] Fabrication of blue organic electroluminescent device

Compound 2 synthesized in Synthesis Example 1 was sublimated to a high purity by a commonly known method, and then a blue organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transfer to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaning the substrate for 5 minutes using UV. The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, DS-205 (Doosan Electronics, 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics, 30 nm) / Compound 2 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in this order to manufacture an organic electroluminescent device. The structures of NPB and ADN used at this time are as follows.

[Examples 2 to 10] Fabrication of blue organic electroluminescent device

Except for using Compounds 5, 7, 8, 25, 41, 66, 68, 71, and 136 synthesized in Synthesis Examples 2 to 10 instead of Compound 2 used in Example 1, respectively, a blue organic electroluminescent device was prepared in the same manner as in Example 1.

[Comparative Example 1] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq ₃ was used instead of Compound 2 used in Example 1. The structure of Alq ₃ used at this time is as follows.

[Comparative Example 2] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound T-1 was used instead of Compound 2 used in Example 1. The structure of T-1 used at this time is as follows.

[Comparative Example 3] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound T-2 was used instead of Compound 2 used in Example 1. The structure of T-2 used at this time is as follows.

[Evaluation Example 1]

For each of the blue organic EL devices manufactured in Examples 1 to 10 and Comparative Examples 1 to 3, driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below.

Sample electron transport layer material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 1 compound 2 3.9 454 8.0 Example 2 compound 5 3.5 456 8.9 Example 3 compound 7 3.8 457 8.3 Example 4 compound 8 3.7 452 8.6 Example 5 compound 25 4.3 455 8.5 Example 6 compound 41 3.7 452 8.3 Example 7 compound 66 3.8 453 7.7 Example 8 compound 68 3.9 454 7.8 Example 9 compound 71 4.0 455 7.9 Example 10 compound 136 4.2 456 6.0 Comparative Example 1 Alq ₃ 5.4 458 4.8 Comparative Example 2 T-1 5.3 459 4.9 Comparative Example 3 T-2 5.2 458 5.1

As shown in Table 1, the blue organic electroluminescent device (Examples 1 to 10) using the compounds (Compounds 2, 5, 7, 8, 25, 41, 66, 68, 71, 136) synthesized in Synthesis Examples 1 to 10 as an electron transport layer material has a drive voltage compared to a blue organic electroluminescent device using Alq ₃ (Comparative Example 1), a conventional electron transport layer material, It was found that excellent performance was exhibited in terms of emission peak and current efficiency.

In addition, the blue organic electroluminescent device (Examples 1 to 10) using the compounds synthesized in Synthesis Examples 1 to 10 (Compounds 2, 5, 7, 8, 25, 41, 66, 68, 71, 136) as an electron transport layer material has a divalent pyridine group as a linking group, so that a compound containing p,p-biphenylene or m,p-biphenylene is used as an electron transport layer material It was found that the blue organic light emitting device (Comparative Examples 2 and 3) exhibited excellent performance in terms of driving voltage, emission peak, and current efficiency.

[Example 11] Fabrication of blue organic electroluminescent device

Compound 2 synthesized in Synthesis Example 1 was sublimated to a high purity by a commonly known method, and then a blue organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, methanol, etc., drying, transfer to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaning the substrate using UV for 5 minutes. The substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, DS-205 (Doosan Electronics Co., Ltd., 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30 nm) / Compound 2 (5 nm) / Alq ₃ (25 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to manufacture an organic electroluminescent device. The structures of NPB and ADN used at this time are as described in Example 1, and the structure of Alq ₃ is as described in Comparative Example 1.

[Examples 12 to 20] Fabrication of blue organic electroluminescent device

Except for using Compounds 5, 7, 8, 25, 41, 66, 68, 71, and 136 synthesized in Synthesis Examples 2 to 10 instead of Compound 2 used in Example 11, a blue organic electroluminescent device was manufactured in the same manner as in Example 11.

[Comparative Example 4] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 11, except that Compound 2 used in Example 11 was not used and Alq ₃ was deposited at 30 nm instead of 25 nm.

[Comparative Example 5] Fabrication of blue organic electroluminescent device

A blue organic light emitting device was manufactured in the same manner as in Example 11, except that Compound T-1 was used instead of Compound 2 used in Example 11. The structure of T-1 used at this time is as described in Comparative Example 2.

[Comparative Example 6] Fabrication of blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example 11, except that Compound T-2 was used instead of Compound 2 used in Example 11. The structure of T-2 used at this time is as described in Comparative Example 3.

[Evaluation Example 2]

For each of the blue organic EL devices manufactured in Examples 11 to 20 and Comparative Examples 4 to 6, driving voltage, emission peak, and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below.

Sample Electron Transport Auxiliary Layer Materials Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 11 compound 2 4.1 452 8.0 Example 12 compound 5 3.7 451 8.4 Example 13 compound 7 4.1 452 7.6 Example 14 compound 8 3.8 454 8.2 Example 15 compound 25 3.7 451 7.3 Example 16 compound 41 4.0 452 8.0 Example 17 compound 66 4.2 453 7.6 Example 18 compound 68 4.1 454 7.5 Example 19 compound 71 3.9 455 7.4 Example 20 compound 136 4.3 456 6.2 Comparative Example 4 - 5.3 458 5.3 Comparative Example 5 T-1 5.4 457 5.3 Comparative Example 6 T-2 5.2 456 5.3

As shown in Table 2, the blue organic electroluminescent devices (Examples 11 to 20) using the compounds (Compounds 2, 5, 7, 8, 25, 41, 66, 68, 71, 136) synthesized in Synthesis Examples 1 to 10 as an electron transport auxiliary layer material have current efficiency, emission peak, and driving voltage compared to the blue organic electroluminescent device without an electron transport auxiliary layer (Comparative Example 4). It was found that the surface showed excellent performance.

In addition, the blue organic electroluminescent device (Examples 11 to 20) using the compounds synthesized in Synthesis Examples 1 to 10 (Compounds 2, 5, 7, 8, 25, 41, 66, 68, 71, 136) as an electron transport auxiliary layer material has a divalent pyridine group as a linking group, thereby electron transporting a compound containing p,p-biphenylene or m,p-biphenylene It was found that the blue organic light emitting device (Comparative Examples 5 and 6) exhibited excellent performance in terms of driving voltage, emission peak, and current efficiency compared to the blue organic light emitting device used as the auxiliary layer material.

[Example 21] Fabrication of green organic electroluminescent device

Compound 2 synthesized in Synthesis Example 1 was sublimated to a high purity by a commonly known method, and then a green organic electroluminescent device was manufactured according to the following procedure.

First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, it was ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then cleaned for 5 minutes using UV and transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, m-MTDATA (60 nm) / TCTA (80 nm) / 90% of compound 2 + 10% of Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in this order to prepare an organic electroluminescent device. The structures of m-MTDATA, TCTA, Ir(ppy) ₃ , and BCP used at this time are as follows, and the structure of Alq ₃ is as described in Comparative Example 1.

[Examples 22 to 30] Fabrication of green organic electroluminescent device

Except for using the compounds 5, 7, 8, 25, 41, 66, 68, 71, and 136 synthesized in Synthesis Examples 2 to 10 instead of the compound used in Example 21, a blue organic electroluminescent device was manufactured in the same manner as in Example 21.

[Comparative Example 7] Fabrication of green organic electroluminescent device

An organic electroluminescent device was manufactured in the same manner as in Example 21, except that CBP was used instead of Compound 2 used in Example 21. The structure of CBP used at this time is as follows.

[Comparative Example 8] Fabrication of green organic electroluminescent device

An organic electroluminescent device was manufactured in the same manner as in Example 21, except that Compound T-1 was used instead of Compound 2 used in Example 21. The structure of T-1 used at this time is as described in Comparative Example 2.

[Comparative Example 9] Fabrication of green organic electroluminescent device

An organic electroluminescent device was manufactured in the same manner as in Example 21, except that Compound T-2 was used instead of Compound 2 used in Example 21. The structure of T-2 used at this time is as described in Comparative Example 3.

[Evaluation example 3]

For each of the green organic electroluminescent devices prepared in Examples 21 to 30 and Comparative Examples 7 to 9, driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 3 below.

Sample host material Driving voltage (V) Emission peak (nm) Current efficiency (cd/A) Example 21 compound 2 6.81 518 39.7 Example 22 compound 5 6.48 518 44.9 Example 23 compound 7 6.66 518 41.3 Example 24 compound 8 6.70 517 41.3 Example 25 compound 25 6.70 515 43.1 Example 26 compound 41 6.51 518 43.5 Example 27 compound 66 6.77 518 41.4 Example 28 compound 68 6.82 517 41.3 Example 29 compound 71 6.66 515 41.3 Example 30 compound 136 6.86 516 41.2 Comparative Example 7 CBP 7.59 516 26.8 Comparative Example 8 T-1 7.34 517 28.9 Comparative Example 9 T-2 7.53 517 31.1

As shown in Table 3, the green organic electroluminescent devices (Examples 21 to 30) using the compounds synthesized in Synthesis Examples 1 to 10 (Compounds 2, 5, 7, 8, 25, 41, 66, 68, 71, 136) as a light emitting layer material exhibited excellent performance in terms of current efficiency and driving voltage compared to the green organic electroluminescent device using CBP, a conventional light emitting layer material (Comparative Example 7). could be seen to indicate

In addition, the green organic electroluminescent device (Examples 21 to 30) using the compounds synthesized in Synthesis Examples 1 to 10 (Compounds 2, 5, 7, 8, 25, 41, 66, 68, 71, 136) as a light emitting layer material has a divalent pyridine group as a linking group, so that a compound containing p,p-biphenylene or m,p-biphenylene is used as an electron transport auxiliary layer material It was found that compared to the blue organic light emitting device used as (Comparative Examples 8 and 9), it exhibited excellent performance in terms of driving voltage, emission peak, and current efficiency.

Claims (11)

A compound represented by Formula 7 or 8:
[Formula 7]

[Formula 8]

In Formulas 7 and 8,
Ar ₁ 및 Ar ₂ 는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C ₁ ~C ₄₀ 의 알킬기, C ₂ ~C ₄₀ 의 알케닐기, C ₂ ~C ₄₀ 의 알키닐기, C ₃ ~C ₄₀ 의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C ₆ ~C ₆₀ 의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C ₁ ~C ₄₀ 의 알킬옥시기, C ₆ ~C ₆₀ 의 아릴옥시기, C ₁ ~C ₄₀ 의 알킬실릴기, C ₆ ~C ₆₀ 의 아릴실릴기, C ₁ ~C ₄₀ 의 알킬보론기, C ₆ ~C ₆₀ 의 아릴보론기, C ₆ ~C ₆₀ 의 아릴포스핀기, C ₆ ~C ₆₀ 의 아릴포스핀옥사이드기 및 C ₆ ~C ₆₀ 의 아릴아민기로 이루어진 군에서 선택되거나, 또는 이들은 인접한 기와 축합 고리를 형성할 수 있으며,
A is a substituent represented by Formula 2 below,
[Formula 2]

In Formula 2,
Y is O, S or CR ₃ R ₄ ;
n and m are each an integer from 0 to 4;
R ₁ 내지 R ₄ 는 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C ₁ ~C ₄₀ 의 알킬기, C ₂ ~C ₄₀ 의 알케닐기, C ₂ ~C ₄₀ 의 알키닐기, C ₃ ~C ₄₀ 의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C ₆ ~C ₆₀ 의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C ₁ ~C ₄₀ 의 알킬옥시기, C ₆ ~C ₆₀ 의 아릴옥시기, C ₁ ~C ₄₀ 의 알킬실릴기, C ₆ ~C ₆₀ 의 아릴실릴기, C ₁ ~C ₄₀ 의 알킬보론기, C ₆ ~C ₆₀ 의 아릴보론기, C ₆ ~C ₆₀ 의 아릴포스핀기, C ₆ ~C ₆₀ 의 아릴포스핀옥사이드기 및 C ₆ ~C ₆₀ 의 아릴아민기로 이루어진 군에서 선택되거나, 또는 이들은 인접한 기와 축합 고리를 형성할 수 있으며,
However, any one of R ₁ to R ₄ is a single bond, which is bonded to Formula 1,
상기 Ar ₁ , Ar ₂ , R ₁ 내지 R ₄ 의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C ₁ ~C ₄₀ 의 알킬기, C ₂ ~C ₄₀ 의 알케닐기, C ₂ ~C ₄₀ 의 알키닐기, C ₃ ~C ₄₀ 의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C ₆ ~C ₆₀ 의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C ₁ ~C ₄₀ 의 알킬옥시기, C ₆ ~C ₆₀ 의 아릴옥시기, C ₁ ~C ₄₀ 의 알킬실릴기, C ₆ ~C ₆₀ 의 아릴실릴기, C ₁ ~C ₄₀ 의 알킬보론기, C ₆ ~C ₆₀ 의 아릴보론기, C ₆ ~C ₆₀ 의 아릴포스핀기, C ₆ ~C ₆₀ 의 아릴포스핀옥사이드기 및 C ₆ ~C ₆₀ 의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이하다. delete delete delete According to claim 1,
Wherein Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently selected from the group consisting of a C ₆ ~ C ₆₀ aryl group and a heteroaryl group having 5 to 60 nuclear atoms. According to claim 1,
A compound wherein Ar ₁ and Ar ₂ are the same as or different from each other, and are each independently a substituent selected from the group consisting of the following Structural Formulas S1 to S8:

In the above structural formula,
* means a site bonded to Formula 1. According to claim 1,
The compound represented by Formula 7 or 8 is a compound selected from the following compounds 1 to 19, 22 to 36, 38 to 48 and 50 to 60:

. According to claim 1,
The compound represented by Formula 7 or 8 is a compound selected from the following compounds 62 to 80, 83 to 97, 99 Nyaja 109 and 111 to 122:

. A compound selected from compounds 123 to 171:

. It includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode,
At least one of the one or more organic material layers includes an organic electroluminescent device comprising the compound according to any one of claims 1 and 5 to 9. According to claim 10,
An organic electroluminescent device wherein the organic material layer containing the compound is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.