KR102307238B1 - Organic compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent device having a low driving voltage, high luminous performance and efficiency, and improved lifespan characteristics by including a novel compound excellent in heat resistance, hole transport ability and electron blocking ability, etc. in one or more organic material layers.

Description

Organic compound and organic electroluminescent device comprising the same

The present invention relates to a novel organic compound and an organic electroluminescent device comprising the same, and more particularly, an arylamine-based compound having excellent heat resistance, electron blocking ability and hole transport ability, and the compound as a material of an organic material layer, thereby providing a low driving voltage And, it relates to an organic electroluminescent device having excellent luminous efficiency and improved lifespan characteristics.

Starting from the observation of organic thin film emission by Bernanose in the 1950s, the organic electroluminescent (EL) device (hereinafter simply referred to as “organic EL device”), which led to blue electroluminescence using anthracene single crystals, was introduced in 1965. In 1987, Tang proposed an organic EL device having a stacked structure divided into a functional layer of a hole layer and a light emitting layer. Since then, in order to improve the efficiency and lifespan of the organic EL device, it has been developed in the form of introducing a characteristic organic material layer in the device, and also led to the development of a specialized material used therefor.

In the organic El device, when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are respectively injected. When the injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. 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, etc. according to their function.

The material for forming the light emitting layer of the organic EL device may be classified into blue, green, and red light emitting materials according to the emission color. In addition, it may be divided into yellow and orange light emitting materials necessary for realizing better natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material.

The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescence, attention is focused on phosphorescent host materials as well as phosphorescent dopants.

To date, the hole injection layer, the hole transport layer. As a material used as a hole blocking layer and an electron transport layer, NPB, BCP, Alq _3, etc. represented by the following chemical formulas are widely known, and anthracene derivatives have been reported as a fluorescent dopant/host material as a light emitting material. In particular, among the light emitting materials, phosphorescent materials having a great advantage in terms of efficiency improvement include metal complex compounds containing Ir such as _{Firpic, Ir(ppy) 3} , (acac)Ir(btp) _{2 , and these are blue and green.} , is used as a red dopant material. So far, CBP has shown excellent properties as a phosphorescent host material.

However, conventional light emitting materials are good in terms of luminescent properties, but have poor thermal stability due to a low glass transition temperature (Tg), so they are not satisfactory in terms of lifespan in organic EL devices. Accordingly, there is a demand for the development of an organic EL device including a light emitting material having excellent performance.

On the other hand, for practical use and improvement of characteristics of the organic EL device, the device should be configured with an organic material layer having the above-described multi-layer structure, and the material of the device, particularly a hole transport material, should have thermal and electrically stable properties. Because molecules with low thermal stability due to heat generated from the device when voltage is applied, a rearrangement phenomenon occurs due to low crystal stability. This is because concentration leads to deterioration and destruction of the device. Therefore, in consideration of the above points, conventionally used hole transport materials include m-MTDATA [4, 4',4"-tris(N-3-methylphenyl-N-phenylamino)-triphenylamine, 2-TNATA [4, 4′,4″-tris(N-(naphthylene-2-yl)-N-phenylamino)-triphenylamine], TPD [N,N′-diphenyl-N,N′-di( 3-methylphenyl)-4,4'-diaminobiphenyl] and NPB [N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine].

However, m-MTDATA and 2-TNATA have low glass transition temperatures (Tg) of 78°C and 108°C, respectively, and many problems occur in the process of mass production, so there is a problem in realizing full color. In addition, since TPD and NPB also have low glass transition temperatures (Tg) of 60°C and 96°C, respectively, there is a fatal disadvantage of shortening the lifetime of the device for the same reason as above. Accordingly, there is a demand for the development of an organic EL device capable of increasing thermal stability and having excellent hole transport ability to increase the luminous efficiency and power efficiency of the organic EL device.

An object of the present invention is to provide a novel organic compound that is excellent in heat resistance, electron blocking ability, and hole transport ability, and can be used as a light emitting auxiliary layer material, a hole transport layer material, a hole injection layer material, and the like.

In addition, it is another object of the present invention to provide an organic electroluminescent device having a low driving voltage, high luminous efficiency, and improved lifespan characteristics, including the novel organic compound described above.

In order to achieve the above object, the present invention provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

Ar ₁ and Ar ₂ are each independently a substituent represented by the following formula (2);

Ar ₃ is a substituent represented by the following formula (3);

[Formula 2]

[Formula 3]

In Formulas 1 to 3,

* is the part where the bond is made;

X ₁ is selected from the group consisting of O, S, N(R ₆ ) and C(R ₇ )(R _{8 );}

at least one of R ₄ to R ₈ forms a bond with _{L 1} or L _{2 ;}

R ₁ to R ₃ and L ₁ or L _{2 and R 4} to R ₈ that do not form a bond are the same as or different from each other, and each independently each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ Aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ aryl silyl group, C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl the Phosphinicosuccinic group and a C ₆ ~ C ₆₀ selected from the group consisting of an arylamine group, or each adjacent R ₄ and R ₅ may be bonded to each other to form a condensed ring;

Ar ₄ and Ar ₅ 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, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group, Ar ₄ and Ar ₅ may form a bond with each other;

L _{1 To} L ₃ are each independently selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;

a and b are each independently an integer from 0 to 4;

The R _{1 To} R ₈ And Ar _{4 To} Ar ₅ Aryl group, heteroaryl group and arylamine group, R _{1 To} R ₈ Alkyl group, cycloalkyl group, heterocycloalkyl group, alkyloxy group, aryloxy group, alkylsilyl group , arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group and mono or diaryl phosphinyl group, L ₁ to L ₃ arylene group, heteroarylene group is each independently, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ Aryl group, the number of nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl Phosphinicosuccinic aryl group and a C ₆ ~ C ₆₀ amine When substituted with one or more selected from the group consisting of a group or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.

According to a preferred embodiment of the present invention,

In Formula 1, L ₁ to L ₃ are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a fluorenyl group, and a pyridinyl group.

According to a preferred embodiment of the present invention,

In Formula 3, Ar ₄ and Ar ₅ are the same as or different from each other, and each independently represents a C ₆ ~ C ₁₈ aryl group or a heteroaryl group having 5 to 18 nuclear atoms.

According to a preferred embodiment of the present invention,

In Formula 3, _{at least one of Ar 4} and Ar ₅ is a substituent represented by Formula 2 above.

According to a preferred embodiment of the present invention,

In Formula 1, X ₁ is O or S,

At least one of R ₄ to R ₅ is characterized in that it forms a bond with _{L 1} or L _{2 .}

According to a preferred embodiment of the present invention,

In Formula 1, X ₁ is N(R ₆ ),

At least one of R ₄ to R ₆ is characterized in that it forms a bond with _{L 1} or L _{2 .}

According to a preferred embodiment of the present invention,

In Formula 1, X ₁ is C(R ₇ )(R ₈ ),

At least one of R ₄ to R ₅ and R ₇ to R ₈ forms a bond with _{L 1} or L _{2 .}

According to a preferred embodiment of the present invention,

In Formula 1, X ₁ is C(R ₇ )(R ₈ ),

R ₇ and R ₈ are each independently a methyl group or a phenyl group, or R ₇ and R ₈ are combined to form a substituent represented by Formula 7 below.

[Formula 7]

In Formula 7,

* means the part where the bond is made.

According to a preferred embodiment of the present invention,

The compound represented by Formula 1 is characterized in that it is represented by any one of Formulas 4 to 6 below.

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 4 to 6,

X ₁ , L ₁ to L _{3 ,} R ₁ to R ₅ , Ar ₄ to Ar ₅ , a and b are the same as defined in Formulas 1 to 3 above.

In addition, the present invention is (i) an anode; (ii) a cathode; and (iii) at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer comprises a compound represented by Formula 1 above. provides

Here, the at least one organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a hole transport layer, an electron blocking layer, and a light emitting auxiliary layer.

In the present invention, "alkyl" refers to a monovalent substituent derived from a saturated hydrocarbon having 1 to 40 carbon atoms in a straight or branched chain. 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 (alkenyl)" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl) and the like.

In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, two or more rings may be simply attached to each other (pendant) or condensed form 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" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. In this case, one or more carbons, preferably 1 to 3 carbons in the ring are 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 further, 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, and carbazolyl, and 2-furanyl, N-imidazolyl, and 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but is not limited thereto.

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

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

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 at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S or a hetero atom such as Se. 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 “aryloxy” 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.

The compound provided in the present invention has excellent heat resistance, electron blocking ability and hole transport ability, and thus can be usefully applied as a material for an organic material layer of an organic electroluminescent device.

In addition, the organic electroluminescent device comprising the compound of the present invention in one or more organic material layers has a low driving voltage, has excellent light emitting performance and efficiency, and has improved lifespan characteristics, and can be effectively applied to full color display panels and the like.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated.

1. Novel Organic Compounds

The present invention is an arylamine-based compound having excellent heat resistance, electron blocking ability, and hole transport ability, and has one arylamine group and two dibenzo moieties (dibenzofuran, dibenzo An object of the present invention is to provide a novel organic compound characterized in that it has a basic core in which thiophene), carbazole, and fluorene are combined.

Specifically, the compound of the present invention may be represented by the following formula (1).

[Formula 1]

In Formula 1,

Ar ₁ and Ar ₂ are each independently a substituent represented by the following formula (2);

Ar ₃ is a substituent represented by the following formula (3);

[Formula 2]

[Formula 3]

In Formulas 1 to 3,

* is the part where the bond is made;

X ₁ is selected from the group consisting of O, S, N(R ₆ ) and C(R ₇ )(R _{8 );}

at least one of R ₄ to R ₈ forms a bond with _{L 1} or L _{2 ;}

R ₁ to R ₃ and L ₁ or L _{2 and R 4} to R ₈ that do not form a bond are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ of alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, Heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group , C ₁ ~ C ₄₀ group of an alkyl boron, C ₆ ~ C group ₆₀ arylboronic of, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C ₆₀ of is selected from the group consisting of an arylamine group, or each adjacent R ₄ and R ₅ may be bonded to each other to form a condensed ring;

Ar ₄ and Ar ₅ 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, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ ~ C ₆₀ arylamine group, By forming a bond with each other, for example, a 5-ring heterocycle, for example, a carbazole structure may be formed, and preferably, Ar ₄ and Ar ₅ are each independently a C ₆ ~ C ₆₀ aryl group or nucleus a heteroaryl group having 5 to 60 atoms, and more preferably, _{each of Ar 4} and Ar ₅ is a substituent represented by Formula 2;

L ₁ to L ₃ are each independently selected from the group consisting of a single bond, a C ₆ to C ₁₈ arylene group and a heteroarylene group having 5 to 18 nuclear atoms, preferably a single bond, phenylene, biphenylene , is selected from the group consisting of fluorenyl and pyridinyl groups;

a and b are each independently an integer from 0 to 4;

The R ₁ to R ₃ and L ₁ or L _{2 and R 4} to R ₈ and Ar ₄ to Ar _{5 that} do not form a bond with an aryl group, a heteroaryl group, and an arylamine group, the R ₁ to R ₃ and of _{R 4} to R _{8 that} do not form a bond with _{L 1} or L ₂ An alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, and a mono or diarylphosphinyl group, L ₁ to L ₃ of arylene group, heteroarylene group are each independently, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, number of nuclear atoms 3 to 40 heterocycloalkyl group, C ₆ ~ C ₆₀ aryl group, 5 to 60 nuclear atoms heteroaryl group, C ₁ ~ C ₄₀ alkyloxy group, C ₆ ~ C ₆₀ aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ Aryl phosphine group, C ₆ ~ C ₆₀ Mono or diarylphosphinyl group and C ₆ ~ C _{60 When} unsubstituted or substituted with one or more selected from the group consisting of an arylamine group, and substituted with a plurality of substituents, they are the same or different from each other.

In the present invention, the organic light emitting compound of Chemical Formula 1 has excellent stability compared to conventional hole transport materials and excellent material lifespan characteristics. There is an advantage that an OLED device can be manufactured.

In addition, since the arylamine group, the dibenzo moiety (dibenzofuran, dibenzothiophene), carbazole, and fluorene each have electron donor (EDG) characteristics, they are stable and have good hole mobility. Therefore, the compound represented by Formula 1 of the present invention, in which the moiety is bonded in an asymmetric structure, is thermally stable and has an advantage as a hole transporting material capable of maximizing efficiency characteristics by improving hole mobility.

Specifically, the compound of Formula 1 of the present invention is used to increase the efficiency of the fluorescent blue device, and its role is to have a hole mobility higher than a certain level (higher than Hole Mobility of NPB), and the T1 value is As it is higher than the blue fluorescent light emitting layer, the main role is to prevent triplet excitons from flowing into the BIL and to increase efficiency by limiting the triplet excitons to singlet excitons through TTA (TTF) by limiting them in the light emitting layer. In this case, preferably, the effect of improving the interface properties between the hole-related layer and the light emitting layer (EML) may also be accompanied, and more preferably, it exhibits a high LUMO value and thus also includes an electron blocking function. can

On the other hand, the light emitting auxiliary layer restricts injection of triplet excitons into the hole-related layer, and at the same time has a delta Est (<0.5 eV) characteristic below a certain level, so that a small amount is introduced into the light emission auxiliary layer. It can serve to move the triplet excitons to the singlet level. This is again transferred to the singlet level of the EML to participate in exciton generation, and as a result, it is transferred to the triplet level of the EML to eliminate the loss of efficiency that may occur when the light emitting auxiliary layer is not provided, or the efficiency of the phosphorescent light emitting layer (EML) serves to increase

However, the compound represented by Formula 1 according to the present invention has an electron-rich basic structure, excellent hole mobility, and a carbazole moiety, dibenzofuran, and dibenzothiophene having high triplet energy. , there is an advantage as a light emitting auxiliary layer material that can maximize efficiency characteristics because it contains a fluorene moiety.

According to a preferred embodiment of the present invention, as described above in Formula 1, X ₁ may be selected from the group consisting of O, S, N(R ₆ ) and C(R ₇ )(R _{8 ), but in one example} When X ₁ is O or S, at least one of _{R 4} to R _{5 may form a bond with L 1} or L _{2 ,} and in another example, when X ₁ is N(R ₆ ), R ₄ to R ₆ at least one may _{form a bond with L 1} or L ₂ , and in another example, when X ₁ is C(R ₇ )(R ₈ ), at least one of _{R 4} to R ₅ and R ₇ to R _{8 .} may _{form a bond with L 1} or L ₂ , and in another example, when X ₁ is C(R ₇ )(R ₈ ), R ₇ and R ₈ are each independently a methyl group or a phenyl group, or the R ₇ and R ₈ may be combined with each other to form a substituent represented by the following Chemical Formula 7, but is not limited thereto.

[Formula 7]

In Chemical Formula 7, * means a portion where a bond is formed.

According to a preferred embodiment of the present invention, the compound represented by Formula 1 is characterized in that it is represented by any one of Formulas 4 to 6 below.

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 4 to 6,

X ₁ , L ₁ to L _{3 ,} R ₁ to R ₅ , Ar ₄ to Ar ₅ , a and b are the same as defined in Formulas 1 to 3.

In addition, in the present invention, the compound represented by Formula 1 may be further specified as a compound represented by any one of the following exemplified Formulas. However, the compound represented by Formula 1 of the present invention is not limited by those exemplified below.

The compound of Formula 1 of the present invention can be synthesized according to a general synthesis method. The detailed synthesis process for the compound of the present invention will be described in detail in the following Synthesis Examples.

2. Organic electroluminescent device

On the other hand, another aspect of the present invention provides an organic electroluminescent device (organic EL device) comprising the compound represented by the above-described formula (1).

Specifically, the organic electroluminescent device according to the present invention includes (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, , At least one of the organic material layer includes a compound represented by the formula (1). In this case, the compound represented by Formula 1 may be used alone or in combination of two or more.

According to an example, the one or more organic material layers may include any one or more of a light emitting layer, a light emitting auxiliary layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, and an electron blocking layer, of which at least one organic material layer is It may include a compound represented by Formula 1 above.

Preferably, the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a light emitting auxiliary layer, a hole transporting layer and an electron blocking layer, and more preferably a light emitting auxiliary layer.

In particular, when the compound represented by Formula 1 is included in an organic electroluminescent device as a light emitting layer material, improvement in luminous efficiency, luminance, power efficiency, thermal stability, and device lifespan of the organic electroluminescent device can be expected.

The structure of the organic electroluminescent device according to the present invention is not particularly limited, and for example, an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. can be

In addition, the organic electroluminescent device may include a life improvement layer or an electron transport auxiliary layer between the light emitting layer and the electron transport layer. In this case, the compound represented by Formula 1 may be used as a life improvement layer or an electron transport auxiliary layer.

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

The organic material layer 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 method.

In the present invention, the substrate usable for manufacturing the organic electroluminescent device is not particularly limited, and for example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film or sheet, etc., but is not limited thereto.

In addition, examples of the anode material include metals such as vanadium, chromium, copper, zinc, 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 and polyaniline; or carbon black, and the like, but is not limited thereto.

Further, examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or an alloy thereof; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

In addition, the hole injection layer material, the hole transport layer material, the electron injection layer material and the electron transport layer material is not particularly limited, and a conventional material known in the art may be used.

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

[Preparation Example 1] Synthesis of Intermediate-1

Under a nitrogen stream, 10 g (31.77 mmol) of 1,3,5-tribromobenzene, 10.62 g (63.53 mmol) of 9H-carbazole, 0.30 g (1.59 mmol) of CuI _, 13.17 g (95.30 mmol) of K ₂ CO _3, 0.57 g (3.18 mmol) of 1,10-phenanthroline and 150 ml of DMF were mixed and stirred at 150° C. for 10 hours. After completion of the reaction, extraction was performed with dichloromethane, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 11.92 g (yield: 77%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 487.39 g/mol, measured: 487 g/mol)

¹ H-NMR: δ 7.30 (m, 7H), 7.50 (t, 2H), 7.60 (m, 4H), 7.90 (d, 2H), 8.10 (d, 2H) , 8.50 (d, 2H)

[Preparation Example 2] Synthesis of Intermediate-2

Under a nitrogen stream, 10.0 g (31.77 mmol) of 1,3,5-tribromobenzene, 18.24 g (63.53 mmol) of 4- (9H-carbazol-9-yl) phenyl boronic acid, 13.17 g (95.30 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.84 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 17.47 g (yield: 86%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 639.58 g/mol, measured: 639 g/mol)

¹ H-NMR: δ 7.30 (m, 6H), 7.40 (m, 4H), 7.60 (m, 7H), 7.80 (d, 4H), 7.92 (d, 2H) , 8.12 (d, 2H) , 8.50 ( d, 2H)

[Preparation Example 3] Synthesis of Intermediate-3

Under a nitrogen stream, 10.0 g (31.77 mmol) of 1,3,5-tribromobenzene, 18.24 g (63.53 mmol) of 9-phenyl-9H-carbazol-3-yl boronic acid, 13.17 g (95.30 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.84 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 15.24 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 639.58 g/mol, measured: 639 g/mol)

¹ H-NMR: δ 7.30 (m, 10H), 7.50 (m, 11H), 7.86 (d, 4H), 8.50 (d, 2H)

[Preparation Example 4] Synthesis of Intermediate-4

Under a nitrogen stream, 10.0 g (31.77 mmol) of 1,3,5-tribromobenzene, 18.24 g (63.53 mmol) of dibenzo [b,d] furan-4-ylboronic acid, 13.17 g (95.30 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of Toluene / H ₂ O / EtOH were added and stirred. 1.84 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 10.88 g (yield: 70%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 489.36 g/mol, measured: 489 g/mol)

¹ H-NMR: δ 7.40 (m, 8H), 7.55 (m, 3H), 7.90 (m, 6H)

[Preparation Example 5] Synthesis of Intermediate-5

Under a nitrogen stream, 10.0 g (31.77 mmol) of 1,3,5-tribromobenzene, 18.24 g (63.53 mmol) of 4-(dibenzo[b,d]furan-4-yl)phenyl boronic acid, 13.17 g (95.30 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.84 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 14.67 g (yield: 72%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 641.55 g/mol, measured: 641 g/mol)

¹ H-NMR: δ 7.25 (m, 16H), 7.70 (m, 3H), 7.85 (m, 6H)

[Preparation Example 6] Synthesis of Intermediate-6

Under a nitrogen stream, 10.0 g (31.77 mmol) of 1,3,5-tribromobenzene, 18.24 g (63.53 mmol) of dibenzo [b,d] thiophen-4-ylboronic acid, 14.49 g (95.30 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.84 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 11.26 g (yield: 68%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 521.49 g/mol, measured: 521 g/mol)

¹ H-NMR: δ 7.50 (m, 6H), 8.10 (d, 2H), 8.20 (d, 2H), 8.40 (m, 4H)

[Preparation Example 7] Synthesis of Intermediate-7

Under a nitrogen stream, 10.0 g (31.77 mmol) of 1,3,5-tribromobenzene, 18.24 g (63.53 mmol) of 4- (dibenzo [b,d] thiophen-4-yl) phenyl boronic acid, 19.32 g (95.30 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of Toluene/H ₂ O/ EtOH were added and stirred. 1.84 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 15.62 g (yield: 73%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 673.68 g/mol, measured: 673 g/mol)

¹ H-NMR: δ 7.30 (m, 16H), 7.75 (m, 3H), 7.90 (m, 6H)

[Preparation Example 8] Synthesis of Intermediate-8

Under a nitrogen stream, 10.0 g (31.77 mmol) of 1,3,5-tribromobenzene, 15.13 g (63.53 mmol) of 9,9-dimethyl-9H-fluoren-2-ylboronic acid, 13.17 g (95.30 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.84 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 13.70 g (yield: 64 %) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 673.68 g/mol, measured: 673 g/mol)

¹ H-NMR: δ 1.70 (s, 12H), 7.30 (t, 2H), 7.40 (m, 4H), 7.55 (m, 5H), 8.12 (m, 4H)

[Preparation Example 9] Synthesis of 2-(3,5-dibromophenyl)-9,9-dimethyl-9H-fluorene

Under nitrogen stream, 10.0 g (31.77 mmol) of 1,3,5-tribromobenzene, 7.56 g (31.77 mmol) of 9,9-dimethyl-9H-fluoren-2-ylboronic acid, 13.17 g (95.30 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.84 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 13.70 g (yield: 64 %) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 428.16 g/mol, measured: 428 g/mol)

¹ H-NMR: δ 1.70 (s, 6H), 7.28 (t, 1H), 7.40 (m, 3H), 7.55 (d, 1H), 7.80 (d, 1H) , 7.90 (s, 1H), 8.10 ( m, 3H)

[Preparation example 10] Synthesis of Intermediate-9

10.0 g (23.36 mmol), 4.95 g (23.36 mmol) of 2-(3,5-dibromophenyl)-9,9-dimethyl-9H-fluorene obtained in Preparation Example 9 under a nitrogen stream of dibenzo[b] ,d]furan-3-ylboronic acid, 9.68 g (70.07 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.35 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 8.55 g (yield: 71%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 515.44 g/mol, measured: 515 g/mol)

¹ H-NMR: δ 1.70 (s, 6H), 7.28 (m, 4H), 7.55 (d, 1H), 7.70 (m, 4H), 7.90 (m, 6H)

[Preparation Example 11] Synthesis of Intermediate-10

10.0 g (23.36 mmol), 5.33 g (23.36 mmol) of 2-(3,5-dibromophenyl)-9,9-dimethyl-9H-fluorene obtained in Preparation Example 9 under a nitrogen stream of dibenzo[b] ,d]thiophen-3-ylboronic acid, 9.68 g (70.07 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.35 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 9.31 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 515.44 g/mol, measured: 515 g/mol)

¹ H-NMR: δ 1.75 (s, 6H), 7.30 (m, 4H), 7.55 (d, 1H), 7.85 (m, 4H), 7.95 (m, 6H)

[Preparation Example 12] Synthesis of Intermediate-11

2-(3,5-dibromophenyl)-9,9-dimethyl-9H-fluorene 10.0 g (23.36 mmol), 6.71 g (23.36 mmol) of 9-phenyl- 9H-carbazol-3-ylboronic acid, 9.68 g (70.07 mmol) of K ₂ CO ₃ and 100 ml / 25 ml / 25 ml of toluene / H ₂ O / EtOH were added and stirred. 1.35 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 13.13 g (yield: 70%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 590.55 g/mol, measured: 590 g/mol)

¹ H-NMR: δ 1.75 (s, 6H), 7.30 (m, 15H), 7.77 (d, 2H), 7.90 (m, 4H), 8.55 (d, 1H)

[Preparation Example 13] Synthesis of Intermediate-12

2-(3,5-dibromophenyl)-9,9-dimethyl-9H-fluorene 10.0 g (23.36 mmol), 3.91 g (23.36 mmol) of 9H-carbazole obtained in Preparation Example 9 under a nitrogen stream , 0.22 g (1.17 mmol) of CuI _, 9.68 g (70.07 mmol) of K ₂ CO _{3 ,} 0.42 g (2.34 mmol) of 1,10-phenanthroline and 150 ml of DMF are mixed and stirred at 150° C. for 10 hours. did. After completion of the reaction, extraction was performed with dichloromethane, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 8.53 g (yield: 71%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 514.45 g/mol, measured: 514 g/mol)

¹ H-NMR: δ 1.75 (s, 6H), 7.40 (m, 15H), 7.80 (d, 2H), 7.90 (m, 4H), 8.55 (d, 1H)

[Synthesis Example 1] Synthesis of A-13

Intermediate-1 (5.0 g, 10.26 mmol), 4-(diphenyl-4-ylamino)phenyl boronic acid (4.53 g, 10.26 mmol), K ₂ CO ₃ ( 4.25 g, 30.78 mmol), toluene/ H ₂ O/ EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.59 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 5.94 g (yield: 72%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 803.99 g/mol, measured: 803 g/mol)

[Synthesis Example 2] Synthesis of A-14

4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl boronic acid instead of 4-(diphenyl-4-yl amino)phenyl boronic acid (4.94 g, 10.26 mmol) was used, and 6.06 g (yield: 70%) of the target compound was obtained in the same manner as in Synthesis Example 1.

GC-Mass (theoretical: 844.05 g/mol, measured: 844 g/mol)

[Synthesis Example 3] Synthesis of A-21

The same procedure as in Synthesis Example 1, except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (3.75 g, 10.26 mmol) was used instead of 4-(diphenyl-4-ylamino)phenyl boronic acid to obtain 5.82 g (yield: 78%) of the target compound.

GC-Mass (theoretical: 727.89 g/mol, measured: 727 g/mol)

[Synthesis Example 4] Synthesis of A-23

Synthesis example except that 4'-(diphenyl-4-ylamino)biphenyl-4-ylboronic acid (5.31 g, 10.26 mmol) is used instead of 4-(diphenyl-4-ylamino)phenyl boronic acid The same procedure as in 1 was followed to obtain 7.31 g (yield: 81 %) of the target compound.

GC-Mass (theoretical: 880.08 g/mol, measured: 880 g/mol)

[Synthesis Example 5] Synthesis of B-11

Intermediate-2 (5.0 g, 7.82 mmol), 4-(diphenylamino)phenylboronic acid (2.26 g, 7.82 mmol), K ₂ CO ₃ (3.24 g, 23.45 mmol), toluene/H ₂ O/ under nitrogen stream EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.45 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 4.71 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 803.09 g/mol, measured: 803 g/mol)

[Synthesis Example 6] Synthesis of B-13

In the same manner as in Synthesis Example 5, except that 4-(dibiphenyl-4-ylamino)phenylboronic acid (5.31 g, 7.82 mmol) was used instead of 4-(diphenylamino)phenylboronic acid, the target compound 5.31 g (yield: 71 %) was obtained.

GC-Mass (theoretical: 956.18 g/mol, measured: 956 g/mol)

[Synthesis Example 7] Synthesis of B-14

Use 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenylboronic acid (3.76 g, 7.82 mmol) instead of 4-(diphenylamino)phenylboronic acid 5.84 g (yield: 75%) of the target compound was obtained in the same manner as in Synthesis Example 5 except that.

GC-Mass (theoretical: 996.24 g/mol, measured: 996 g/mol)

[Synthesis Example 8] Synthesis of B-21

The same procedure as in Synthesis Example 5 was performed except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (2.86 g, 7.82 mmol) was used instead of 4-(diphenylamino)phenylboronic acid. Compound 4.95 g (yield: 72 %) was obtained.

GC-Mass (theoretical: 880.08 g/mol, measured: 880 g/mol)

[Synthesis Example 9] Synthesis of C-11

Intermediate-3 (5.0 g, 7.82 mmol), 4-(diphenylamino)phenylboronic acid (2.26 g, 7.82 mmol), K ₂ CO ₃ (3.24 g, 23.45 mmol), toluene/H ₂ O/ under a nitrogen stream EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.45 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 5.09 g (yield: 81%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 803.99 g/mol, measured: 803 g/mol)

[Synthesis Example 10] Synthesis of C-13

In the same manner as in Synthesis Example 9, except that 4-(dibiphenyl-4-ylamino)phenylboronic acid (3.45 g, 7.82 mmol) was used instead of 4-(diphenylamino)phenylboronic acid, the target compound 5.29 g (yield: 79 %) was obtained.

GC-Mass (theoretical: 856.18 g/mol, measured: 856 g/mol)

[Synthesis Example 11] Synthesis of C-14

Use 4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenylboronic acid (3.76 g, 7.82 mmol) instead of 4-(diphenylamino)phenylboronic acid The same procedure as in Synthesis Example 9 was performed except that 6.54 g (yield: 84%) of the target compound was obtained.

GC-Mass (theoretical: 996.24 g/mol, measured: 996 g/mol)

[Synthesis Example 12] Synthesis of C-21

The same procedure as in Synthesis Example 9 was followed except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (2.86 g, 7.82 mmol) was used instead of 4-(diphenylamino)phenylboronic acid. 5.23 g (yield: 76 %) of the compound was obtained.

GC-Mass (theoretical: 880.08 g/mol, measured: 880 g/mol)

[Synthesis Example 13] Synthesis of D-13

Intermediate-4 (5.0 g, 10.22 mmol), 4-(dibiphenyl-4-ylamino)phenylboronic acid (4.51 g, 10.22 mmol), K ₂ CO ₃ (4.24 g, 30.65 mmol), toluene/ H ₂ O/ EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.59 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 5.85 g (yield: 72%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 805.96 g/mol, measured: 805 g/mol)

[Synthesis Example 14] Synthesis of D-14

4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenylboronic acid instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid (4.92 g, 10.22 mmol) was used, and 6.48 g (yield: 75%) of the target compound was obtained in the same manner as in Synthesis Example 13.

GC-Mass (theoretical: 846.02 g/mol, measured: 846 g/mol)

[Synthesis Example 15] Synthesis of D-21

The same procedure as in Synthesis Example 13, except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (3.73 g, 10.22 mmol) was used instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid to obtain 5.29 g (yield: 71 %) of the target compound.

GC-Mass (theoretical: 729.86 g/mol, measured: 729 g/mol)

[Synthesis Example 16] Synthesis of D-23

Synthesis example except for using 4'-(dibiphenyl-4-ylamino)biphenyl-4-ylboronic acid (5.29 g, 10.22 mmol) instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid 13 was performed to obtain 6.31 g (yield: 70 %) of the target compound.

GC-Mass (theoretical: 882.05 g/mol, measured: 882 g/mol)

[Synthesis Example 17] Synthesis of E-11

Intermediate-5 (5.0 g, 7.79 mmol), 4-(dibiphenyl-4-ylamino)phenylboronic acid (3.44 g, 7.79 mmol), K ₂ CO ₃ (3.23 g, 23.38 mmol), toluene/ H ₂ O/ EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.45 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 5.60 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 958.15 g/mol, measured: 958 g/mol)

[Synthesis Example 18] Synthesis of E-12

4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenylboronic acid instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid (3.75 g, 7.79) mmol) was used, and 5.21 g (yield: 67 %) of the target compound was obtained in the same manner as in Synthesis Example 17.

GC-Mass (Theory: 998.21 g/mol, Measured: 998 g/mol)

[Synthesis Example 19] Synthesis of E-19

The same procedure as in Synthesis Example 17 except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (2.85 g, 7.79 mmol) was used instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid was performed to obtain 4.81 g (yield: 70%) of the target compound.

GC-Mass (theoretical: 882.05 g/mol, measured: 882 g/mol)

[Synthesis Example 20] Synthesis of F-13

Intermediate-6 (5.0 g, 9.59 mmol), 4-(dibiphenyl-4-ylamino)phenylboronic acid (4.23 g, 9.59 mmol), K ₂ CO ₃ (3.98 g, 28.76 mmol), toluene/ H ₂ O/ EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.55 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 6.67 g (yield: 83%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 838.09 g/mol, measured: 838 g/mol)

[Synthesis Example 21] Synthesis of F-14

4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenylboronic acid instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid (4.62 g, 9.59 mmol) was used, and 7.16 g (yield: 85%) of the target compound was obtained in the same manner as in Synthesis Example 20.

GC-Mass (theoretical: 878.15 g/mol, measured: 878 g/mol)

[Synthesis Example 22] Synthesis of F-21

The same procedure as in Synthesis Example 20, except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (3.50 g, 9.59 mmol) was used instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid to obtain 5.99 g (yield: 82%) of the target compound.

GC-Mass (theoretical: 761.99 g/mol, measured: 761 g/mol)

[Synthesis Example 23] Synthesis of F-22

Synthesis example except for using 4'-(dibiphenyl-4-ylamino)biphenyl-4-ylboronic acid (4.96 g, 9.59 mmol) instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid 20 was followed to obtain 6.66 g (yield: 76 %) of the target compound.

GC-Mass (theoretical: 914.18 g/mol, measured: 914 g/mol)

[Synthesis Example 24] Synthesis of G-11

Intermediate-7 (5.0 g, 7.42 mmol), 4-(dibiphenyl-4-ylamino)phenylboronic acid (3.28 g, 7.42 mmol), K ₂ CO ₃ (3.08 g, 22.27 mmol), toluene/ H ₂ O/ EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.43 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 5.51 g (yield: 75%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 990.28 g/mol, measured: 990 g/mol)

[Synthesis Example 25] Synthesis of G-12

4-(biphenyl-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenylboronic acid instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid (3.57 g, 7.42 mmol) was used, and 5.43 g (yield: 71 %) of the target compound was obtained in the same manner as in Synthesis Example 24.

GC-Mass (theoretical: 1030.34 g/mol, measured: 1030 g/mol)

[Synthesis Example 26] Synthesis of G-19

The same procedure as in Synthesis Example 24, except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (3.57 g, 7.42 mmol) was used instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid to obtain 5.22 g (yield: 77 %) of the target compound.

GC-Mass (theoretical: 914.18 g/mol, measured: 914 g/mol)

[Synthesis Example 27] Synthesis of H-9

Intermediate-8 (5.0 g, 9.23 mmol), 4-(diphenylamino)phenylboronic acid (2.67 g, 9.23 mmol), K ₂ CO ₃ (10.12 g, 27.70 mmol), toluene/H ₂ O/ under a nitrogen stream EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.53 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 4.76 g (yield: 73%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 705.93 g/mol, measured: 705 g/mol)

[Synthesis Example 28] Synthesis of H-11

The target compound was carried out in the same manner as in Synthesis Example 27, except that 4-(dibiphenyl-4-ylamino)phenylboronic acid (4.07 g, 9.23 mmol) was used instead of 4-(diphenylamino)phenylboronic acid. 5.55 g (yield: 70 %) were obtained.

GC-Mass (theoretical: 858.12 g/mol, measured: 858 g/mol)

[Synthesis Example 29] Synthesis of H-17

The same procedure as in Synthesis Example 27 was performed except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (3.37 g, 9.23 mmol) was used instead of 4-(diphenylamino)phenylboronic acid. 5.05 g (yield: 70 %) of the compound was obtained.

GC-Mass (theoretical: 782.02 g/mol, measured: 782 g/mol)

[Synthesis Example 30] Synthesis of H-19

The same procedure as in Synthesis Example 27, except that 4'-(dibiphenyl-4-ylamino)biphenyl-4-ylboronic acid (4.78 g, 9.23 mmol) was used instead of 4-(diphenylamino)phenylboronic acid was performed to obtain 6.56 g (yield: 76 %) of the target compound.

GC-Mass (theoretical: 934.21 g/mol, measured: 934 g/mol)

[Synthesis Example 31] Synthesis of I-11

Intermediate-9 (5.0 g, 9.70 mmol), 4-(dibiphenyl-4-ylamino)phenylboronic acid (4.28 g, 9.70 mmol), K ₂ CO ₃ (10.63 g, 29.10 mmol), toluene/ H ₂ O/ EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.59 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 5.65 g (yield: 70%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 832.04 g/mol, measured: 832 g/mol)

[Synthesis Example 32] Synthesis of I-12

4-(biphenyl-4-yl(dibenzo[b,d]furan-3-yl)amino)phenylboronic acid instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid (4.42 g, 9.70 mmol) 5.99 g (yield: 73%) of the target compound was obtained in the same manner as in Synthesis Example 31 except for using .

GC-Mass (theoretical: 846.02 g/mol, measured: 846 g/mol)

[Synthesis Example 33] Synthesis of I-17

The same procedure as in Synthesis Example 31, except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (3.54 g, 9.70 mmol) was used instead of 4-(dibiphenyl-4-ylamino)phenylboronic acid to obtain 6.01 g (yield: 82%) of the target compound.

GC-Mass (theoretical: 755.94 g/mol, measured: 755 g/mol)

[Synthesis Example 34] Synthesis of K-9

Intermediate-10 (5.0 g, 8.47 mmol), 4-(diphenylamino)phenylboronic acid (2.45 g, 8.47 mmol), K ₂ CO ₃ (9.28 g, 25.40 mmol), toluene/H ₂ O/ under a nitrogen stream EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.49 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 5.11 g (yield: 80%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 754.96 g/mol, measured: 754 g/mol)

[Synthesis Example 35] Synthesis of K-11

In the same manner as in Synthesis Example 34, except for using 4-(dibiphenyl-4-ylamino)phenylboronic acid (3.74 g, 8.47 mmol) instead of 4-(diphenylamino)phenylboronic acid, the target compound 5.11 g (yield: 80 %) was obtained.

GC-Mass (theoretical: 754.96 g/mol, measured: 754 g/mol)

[Synthesis Example 36] Synthesis of K-17

The same procedure as in Synthesis Example 34 was performed except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (3.09 g, 8.47 mmol) was used instead of 4-(diphenylamino)phenylboronic acid. 5.42 g (yield: 77 %) of the compound was obtained.

GC-Mass (theoretical: 831.05 g/mol, measured: 831 g/mol)

[Synthesis Example 37] Synthesis of L-9

Intermediate-11 (5.0 g, 9.72 mmol), 4-(diphenylamino)phenylboronic acid (2.81 g, 9.72 mmol), K ₂ CO ₃ ( 10.65 g, 29.16 mmol), toluene/H ₂ O/ under a nitrogen stream EtOH (100 ml / 25 ml / 25 ml) was added and stirred. 0.56 g (5 mol%) of Pd(PPh ₃ ) ₄ was added at 40° C. and stirred at 100° C. for 5 hours. After completion of the reaction, extraction was performed with methylene chloride, and MgSO ₄ was added thereto, followed by filtration. After removing the solvent of the filtered organic layer, 6.60 g (yield: 74%) of the target compound was obtained by column chromatography.

GC-Mass (theoretical: 678.86 g/mol, measured: 678 g/mol)

[Synthesis Example 38] Synthesis of L-11

In the same manner as in Synthesis Example 37, except that 4-(dibiphenyl-4-ylamino)phenylboronic acid (4.29 g, 9.72 mmol) was used instead of 4-(diphenylamino)phenylboronic acid, the target compound 5.73 g (yield: 71 %) was obtained.

GC-Mass (theoretical: 831.05 g/mol, measured: 831 g/mol)

[Synthesis Example 39] Synthesis of L-17

The same procedure as in Synthesis Example 37 was performed except that 4'-(diphenylamino)biphenyl-4-ylboronic acid (3.55 g, 9.72 mmol) was used instead of 4-(diphenylamino)phenylboronic acid. Compound 5.65 g (yield: 77 %) was obtained.

GC-Mass (theoretical: 754.96 g/mol, measured: 754 g/mol)

[Example 1] Preparation of organic EL device

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. Then, the substrate was transferred to a vacuum laminating machine.

On the ITO transparent electrode prepared as above, each compound of m-MTDATA (60 nm) / A-1 to M-24 (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq3 ( An organic EL device was manufactured in the order of 30 nm)/LiF (1 nm)/Al (200 nm).

DS-H522 and DS-501 used for device fabrication are products of Doosan Electronics BG. The structures of m-MTDATA, TCTA, CBP, Ir(ppy) ₃ , and BCP are as follows.

[Example A-2 to A-330] Preparation of organic EL device

An organic EL device was manufactured in the same manner as in Example 1, except that Compounds A-2 to L-24 were used instead of Compound A-1 used as a material for the hole transport layer when the hole transport layer was formed in Example 1.

[Comparative Example 1] Fabrication of organic EL device

An organic EL device was manufactured in the same manner as in Example 1, except that NPB was used as a hole transport layer material instead of Compound A-1 used as a hole transport layer material when the hole transport layer was formed in Example 1. The structure of the NPB used is as follows.

[Evaluation Example 1]

For the organic EL devices prepared in Examples A-1 to A-330 and Comparative Example 1, respectively, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example A-1 Compound A-1 4.1 22.2 Example A-2 compound A-2 4.3 20.1 Example A-3 compound A-3 4.4 21.3 Example A-4 Compound A-4 4 22.6 Example A-5 compound A-5 4.5 19.5 Example A-6 compound A-6 4.7 20.1 Example A-7 compound A-7 4.3 21.6 Example A-8 compound A-8 4.5 20.5 Example A-9 compound A-9 4.7 20.6 Example A-10 Compound A-10 4.4 21.6 Example A-11 Compound A-11 5 20.1 Example A-12 Compound A-12 5.1 18.6 Example A-13 compound A-13 4.3 22 Example A-14 Compound A-14 4.6 21.2 Example A-15 Compound A-15 4.5 21.2 Example A-16 Compound A-16 4.4 22.3 Example A-17 Compound A-17 5.1 18.3 Example A-18 Compound A-18 5 18.9 Example A-19 Compound A-19 4.5 21.7 Example A-20 Compound A-20 4.7 21.2 Example A-21 Compound A-21 4.8 20.8 Example A-22 Compound A-22 4.5 21.4 Example A-23 Compound A-23 5.1 18.2 Example A-24 Compound A-24 5.1 18.5 Example A-25 Compound A-25 4.3 22.3 Example A-26 Compound A-26 4.6 21.4 Example A-27 Compound A-27 4.8 21.6 Example A-28 Compound A-28 4.2 22.5 Example A-29 Compound A-29 4.7 20.6 Example A-30 compound A-30 4.6 20.2 Example A-31 compound B-1 4.2 22.1 Example A-32 compound B-2 4.6 21.2 Example A-33 compound B-3 4.8 20 Example A-34 compound B-4 4.2 22.3 Example A-35 compound B-5 4.8 21.8 Example A-36 compound B-6 5 19.2 Example A-37 compound B-7 4.5 20.3 Example A-38 compound B-8 5.1 18.5 Example A-39 compound B-9 4.9 20.3 Example A-40 compound B-10 4.8 20.8 Example A-41 compound B-11 4.2 21.4 Example A-42 compound B-12 4.7 18.2 Example A-43 compound B-13 4.6 18.5 Example A-44 compound B-14 4.2 22.3 Example A-45 compound B-15 4.6 21.4 Example A-46 Compound B-16 4.8 21.6 Example A-47 compound B-17 4.2 22.5 Example A-48 compound B-18 4.8 20.6 Example A-49 compound B-19 4.8 20 Example A-50 compound B-20 4.2 22.3 Example A-51 compound B-21 4.8 21.8 Example A-52 compound C-1 5 19.2 Example A-53 compound C-2 4.5 20.3 Example A-54 compound C-3 5.1 18.5 Example A-55 compound C-4 4.9 20.3 Example A-56 compound C-5 4.8 20.8 Example A-57 compound C-6 4.2 21.4 Example A-58 compound C-7 4.7 18.2 Example A-59 compound C-8 4.6 18.5 Example A-60 compound C-9 4.2 22.3 Example A-61 compound C-10 4.6 21.4 Example A-62 compound C-11 4.8 21.6 Example A-63 compound C-12 4.2 22.5 Example A-64 compound C-13 4.8 20.6 Example A-65 compound C-14 5 20.2 Example A-66 compound C-15 4.5 20.8 Example A-67 compound C-16 4.5 20.3 Example A-68 compound C-17 5.1 18.5 Example A-69 compound C-18 4.9 20.3 Example A-70 compound C-19 4.8 20.8 Example A-71 compound C-20 4.2 21.4 Example A-72 compound C-21 4.7 18.2 Example A-73 compound D-01 4.1 22.2 Example A-74 compound D-02 4.3 20.1 Example A-75 compound D-03 4.4 21.3 Example A-76 compound D-04 4 22.6 Example A-77 compound D-05 4.5 19.5 Example A-78 compound D-06 4.7 20.1 Example A-79 compound D-07 4.3 21.6 Example A-80 compound D-08 4.5 20.5 Example A-81 compound D-09 4.7 20.6 Example A-82 compound D-10 4.4 21.6 Example A-83 compound D-11 5 20.1 Example A-84 compound D-12 5.1 18.6 Example A-85 compound D-13 4.3 22 Example A-86 compound D-14 4.6 21.2 Example A-87 compound D-15 4.5 21.2 Example A-88 compound D-16 4.4 22.3 Example A-89 compound D-17 5.1 18.3 Example A-90 compound D-18 5 18.9 Example A-91 compound D-19 4.5 21.7 Example A-92 compound D-20 4.7 21.2 Example A-93 compound D-21 4.8 20.8 Example A-94 compound D-22 4.5 21.4 Example A-95 compound D-23 5.1 18.2 Example A-96 compound D-24 5.1 18.5 Example A-97 compound D-25 4.3 22.3 Example A-98 compound D-26 4.6 21.4 Example A-99 compound D-27 4.8 21.6 Example A-100 compound D-28 4.2 22.5 Example A-101 compound D-29 4.7 20.6 Example A-102 compound D-30 4.6 20.2 Example A-103 compound E-1 4.2 22.1 Example A-104 compound E-2 4.6 21.2 Example A-105 compound E-3 4.8 20 Example A-106 compound E-4 4.2 22.3 Example A-107 compound E-5 4.8 21.8 Example A-108 compound E-6 5 19.2 Example A-109 compound E-7 4.5 20.3 Example A-110 compound E-8 5.1 18.5 Example A-111 compound E-9 4.9 20.3 Example A-112 compound E-10 4.8 20.8 Example A-113 compound E-11 4.2 21.4 Example A-114 Compound E-12 4.7 18.2 Example A-115 compound E-13 4.6 18.5 Example A-116 compound E-14 4.2 22.3 Example A-117 Compound E-15 4.6 21.4 Example A-118 Compound E-16 4.8 21.6 Example A-119 compound E-17 4.2 22.5 Example A-120 compound E-18 4.8 20.6 Example A-121 compound E-19 4.8 20 Example A-122 compound E-20 4.2 22.3 Example A-123 Compound E-21 4.8 21.8 Example A-124 compound E-22 5 19.2 Example A-125 compound E-23 4.5 20.3 Example A-126 Compound E-24 5.1 18.5 Example A-127 compound E-25 4.9 20.3 Example A-128 compound E-26 4.8 20.8 Example A-129 Compound E-27 4.2 21.4 Example A-130 compound F-1 4.7 18.2 Example A-131 compound F-2 4.6 18.5 Example A-132 compound F-3 4.2 22.3 Example A-133 compound F-4 4.6 21.4 Example A-134 compound F-5 4.8 21.6 Example A-135 compound F-6 4.2 22.5 Example A-136 compound F-7 4.8 20.6 Example A-137 compound F-8 5 20.2 Example A-138 compound F-9 4.5 20.8 Example A-139 compound F-10 4.5 20.3 Example A-140 compound F-11 5.1 18.5 Example A-141 compound F-12 4.9 20.3 Example A-142 compound F-13 4.8 20.8 Example A-143 compound F-14 4.2 21.4 Example A-144 compound F-15 4.7 18.2 Example A-145 compound F-16 4.1 22.2 Example A-146 compound F-17 4.3 20.1 Example A-147 compound F-18 4.4 21.3 Example A-148 compound F-19 4 22.6 Example A-149 compound F-20 4.5 19.5 Example A-150 compound F-21 4.7 20.1 Example A-151 compound F-22 4.3 21.6 Example A-152 compound F-23 4.5 20.5 Example A-153 compound F-24 4.7 20.6 Example A-154 compound F-25 4.4 21.6 Example A-155 compound F-26 5 20.1 Example A-156 compound F-27 5.1 18.6 Example A-157 compound F-28 4.3 22 Example A-158 compound F-29 4.6 21.2 Example A-159 compound F-30 4.5 21.2 Example A-160 compound G-1 4.4 22.3 Example A-161 compound G-2 5.1 18.3 Example A-162 compound G-3 5 18.9 Example A-163 compound G-4 4.5 21.7 Example A-164 compound G-5 4.7 21.2 Example A-165 compound G-6 4.8 20.8 Example A-166 compound G-7 4.5 21.4 Example A-167 compound G-8 5.1 18.2 Example A-168 compound G-9 5.1 18.5 Example A-169 compound G-10 4.3 22.3 Example A-170 compound G-11 4.6 21.4 Example A-171 compound G-12 4.8 21.6 Example A-172 compound G-13 4.2 22.5 Example A-173 compound G-14 4.7 20.6 Example A-174 compound G-15 4.6 20.2 Example A-175 compound G-16 4.2 22.1 Example A-176 compound G-17 4.6 21.2 Example A-177 compound G-18 4.8 20 Example A-178 compound G-19 4.2 22.3 Example A-179 compound G-20 4.8 21.8 Example A-180 compound G-21 5 19.2 Example A-181 compound G-22 4.5 20.3 Example A-182 compound G-23 5.1 18.5 Example A-183 compound G-24 4.9 20.3 Example A-184 compound G-25 4.8 20.8 Example A-185 compound G-26 4.2 21.4 Example A-186 compound G-27 4.7 18.2 Example A-187 compound H-1 4.6 18.5 Example A-188 compound H-2 4.2 22.3 Example A-189 compound H-3 4.6 21.4 Example A-190 compound H-4 4.8 21.6 Example A-191 compound H-5 4.2 22.5 Example A-192 compound H-6 4.8 20.6 Example A-193 compound H-7 4.8 20 Example A-194 compound H-8 4.2 22.3 Example A-195 compound H-9 4.8 21.8 Example A-196 compound H-10 5 19.2 Example A-197 compound H-11 4.5 20.3 Example A-198 compound H-12 5.1 18.5 Example A-199 compound H-13 4.9 20.3 Example A-200 compound H-14 4.8 20.8 Example A-201 compound H-15 4.2 21.4 Example A-202 compound H-16 4.7 18.2 Example A-203 compound H-17 4.6 18.5 Example A-204 compound H-18 4.2 22.3 Example A-205 compound H-19 4.6 21.4 Example A-206 compound H-20 4.8 21.6 Example A-207 compound H-21 4.2 22.5 Example A-208 compound H-22 4.8 20.6 Example A-209 compound H-23 5 20.2 Example A-210 compound H-24 4.5 20.8 Example A-211 compound I-1 4.5 20.3 Example A-212 compound I-2 5.1 18.5 Example A-213 compound I-3 4.9 20.3 Example A-214 compound I-4 4.8 20.8 Example A-215 compound I-5 4.2 21.4 Example A-216 compound I-6 4.7 18.2 Example A-217 compound I-7 4.1 22.2 Example A-218 compound I-8 4.3 20.1 Example A-219 compound I-9 4.4 21.3 Example A-220 compound I-10 4 22.6 Example A-221 compound I-11 4.5 19.5 Example A-222 compound I-12 4.7 20.1 Example A-223 compound I-13 4.3 21.6 Example A-224 compound I-14 4.5 20.5 Example A-225 compound I-15 4.7 20.6 Example A-226 compound I-16 4.4 21.6 Example A-227 compound I-17 5 20.1 Example A-228 compound I-18 5.1 18.6 Example A-229 compound I-19 4.3 22 Example A-230 compound I-20 4.6 21.2 Example A-231 compound I-21 4.5 21.2 Example A-232 compound I-22 4.4 22.3 Example A-233 compound I-23 5.1 18.3 Example A-234 compound I-24 5 18.9 Example A-235 compound J-1 4.5 21.7 Example A-236 compound J-2 4.7 21.2 Example A-237 compound J-3 4.8 20.8 Example A-238 compound J-4 4.5 21.4 Example A-239 compound J-5 5.1 18.2 Example A-240 compound J-6 5.1 18.5 Example A-241 compound J-7 4.3 22.3 Example A-242 compound J-8 4.6 21.4 Example A-243 compound J-9 4.8 21.6 Example A-244 compound J-10 4.2 22.5 Example A-245 compound J-11 4.7 20.6 Example A-246 compound J-12 4.6 20.2 Example A-247 compound J-13 4.2 22.1 Example A-248 compound J-14 4.6 21.2 Example A-249 compound J-15 4.8 20 Example A-250 compound J-16 4.2 22.3 Example A-251 compound J-17 4.8 21.8 Example A-252 compound J-18 5 19.2 Example A-253 compound J-19 4.5 20.3 Example A-254 compound J-20 5.1 18.5 Example A-255 compound J-21 4.9 20.3 Example A-256 compound J-22 4.8 20.8 Example A-257 compound J-23 4.2 21.4 Example A-258 compound J-24 4.7 18.2 Example A-259 compound K-1 4.6 18.5 Example A-260 compound K-2 4.2 22.3 Example A-261 compound K-3 4.6 21.4 Example A-262 compound K-4 4.8 21.6 Example A-263 compound K-5 4.2 22.5 Example A-264 compound K-6 4.8 20.6 Example A-265 compound K-7 4.8 20 Example A-266 compound K-8 4.2 22.3 Example A-267 compound K-9 4.8 21.8 Example A-268 compound K-10 5 19.2 Example A-269 compound K-11 4.5 20.3 Example A-270 compound K-12 5.1 18.5 Example A-271 compound K-13 4.9 20.3 Example A-272 compound K-14 4.8 20.8 Example A-273 compound K-15 4.2 21.4 Example A-274 compound K-16 4.7 18.2 Example A-275 compound K-17 4.6 18.5 Example A-276 compound K-18 4.2 22.3 Example A-277 compound K-19 4.6 21.4 Example A-278 compound K-20 4.8 21.6 Example A-279 compound K-21 4.2 22.5 Example A-280 compound K-22 4.8 20.6 Example A-281 compound K-23 5 20.2 Example A-282 compound K-24 4.5 20.8 Example A-283 compound L-1 4.5 20.3 Example A-284 compound L-2 5.1 18.5 Example A-285 compound L-3 4.9 20.3 Example A-286 compound L-4 4.8 20.8 Example A-287 compound L-5 4.2 21.4 Example A-288 compound L-6 4.7 18.2 Example A-289 compound L-7 4.8 21.6 Example A-290 compound L-8 4.2 22.5 Example A-291 compound L-9 4.8 20.6 Example A-292 compound L-10 4.8 20 Example A-293 compound L-11 4.2 22.3 Example A-294 compound L-12 4.8 21.8 Example A-295 compound L-13 5 19.2 Example A-296 compound L-14 4.5 20.3 Example A-297 compound L-15 5.1 18.5 Example A-298 compound L-16 4.9 20.3 Example A-299 compound L-17 4.8 20.8 Example A-300 compound L-18 4.2 21.4 Example A-301 compound L-19 4.7 18.2 Example A-302 compound L-20 4.6 18.5 Example A-303 compound L-21 4.2 22.3 Example A-304 compound L-22 4.6 21.4 Example A-305 compound L-23 4.8 21.6 Example A-306 compound L-24 4.2 22.5 Example A-307 compound L-1 4.8 20.6 Example A-308 compound L-2 5 20.2 Example A-309 compound L-3 4.5 20.8 Example A-310 compound L-4 4.5 20.3 Example A-311 compound L-5 5.1 18.5 Example A-312 compound L-6 4.9 20.3 Example A-313 compound L-7 4.8 20.8 Example A-314 compound L-8 4.2 21.4 Example A-315 compound L-9 4.7 18.2 Example A-316 compound L-10 4.8 20.6 Example A-317 compound L-11 5 20.2 Example A-318 compound L-12 4.5 20.8 Example A-319 compound L-13 4.5 20.3 Example A-320 compound L-14 5.1 18.5 Example A-321 compound L-15 4.9 20.3 Example A-322 compound L-16 4.8 20.8 Example A-323 compound L-17 4.2 21.4 Example A-324 compound L-18 4.7 18.2 Example A-325 compound L-19 4.6 18.5 Example A-326 compound L-20 4.2 22.3 Example A-327 compound L-21 4.6 21.4 Example A-328 compound L-22 4.8 21.6 Example A-329 compound L-23 4.2 22.5 Example A-330 compound L-24 5.1 18.5 Comparative Example 1 NPB 5.2 18.1

As shown in Table 1 above, the organic EL devices (organic EL devices prepared in Examples A-1 to A-330, respectively) using the compound according to the present invention as the hole transport layer were compared to the conventional organic EL devices using NPB (comparison). It was found that compared to the organic EL device of Example 1), it showed better performance in terms of current efficiency and driving voltage.

[Example B-1] Preparation of green organic electroluminescent device

After high-purity sublimation purification of Compound 1 synthesized in Synthesis Example 1 by a commonly known method, a green organic electroluminescent device was prepared as follows.

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1500 Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. After cleaning, the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, each compound of m-MTDATA (60 nm)/TCTA (80 nm)/A-1 to M-24 (40 nm)/CBP + 10% Ir(ppy)3 (30 nm) /BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device.

The structures of m-MTDATA, TCTA, Ir(ppy)3, CBP and BCP used are as follows.

[Example B-2 ~ B-330] Preparation of green organic electroluminescent device

An organic EL device was manufactured in the same manner as in Example B-1, except that Compounds A-2 to M-24 were used instead of Compound A-1 in Example B-1.

[Comparative Example 2] Preparation of green organic electroluminescent device

A green organic electroluminescent device was prepared in the same manner as in Example B-1, except that Compound A-1 was not used in Example B-1.

[Evaluation Example 2]

For the organic electroluminescent devices prepared in Examples B-1 to B-330, and Comparative Example 2, respectively, the driving voltage, current efficiency, and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in the table below 2 is shown.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example B-1 Compound A-1 6.7 41.9 Example B-2 compound A-2 6.85 42.1 Example B-3 compound A-3 6.8 44.8 Example B-4 Compound A-4 6.8 47.5 Example B-5 compound A-5 6.85 41.5 Example B-6 compound A-6 6.9 41.9 Example B-7 compound A-7 6.95 42.4 Example B-8 compound A-8 6.8 42.3 Example B-9 compound A-9 6.9 45.2 Example B-10 Compound A-10 6.8 44.6 Example B-11 Compound A-11 6.7 44.1 Example B-12 Compound A-12 6.65 43.6 Example B-13 compound A-13 6.7 42.6 Example B-14 Compound A-14 6.9 44.1 Example B-15 Compound A-15 6.8 42.8 Example B-16 Compound A-16 6.7 41.4 Example B-17 Compound A-17 6.7 41.8 Example B-18 Compound A-18 6.65 45.3 Example B-19 Compound A-19 6.7 45.1 Example B-20 Compound A-20 6.65 42.6 Example B-21 Compound A-21 6.6 41.3 Example B-22 Compound A-22 6.6 42.1 Example B-23 Compound A-23 6.7 41.9 Example B-24 Compound A-24 6.9 42.1 Example B-25 Compound A-25 6.8 44.8 Example B-26 Compound A-26 6.8 47.5 Example B-27 Compound A-27 6.85 41.5 Example B-28 Compound A-28 6.85 41.9 Example B-29 Compound A-29 6.65 42.4 Example B-30 compound A-30 6.6 42.3 Example B-31 compound B-1 6.7 45.2 Example B-32 compound B-2 6.85 44.6 Example B-33 compound B-3 6.7 44.1 Example B-34 compound B-4 6.8 43.6 Example B-35 compound B-5 6.75 42.6 Example B-36 compound B-6 6.8 44.1 Example B-37 compound B-7 6.8 42.8 Example B-38 compound B-8 6.85 41.4 Example B-39 compound B-9 6.9 41.8 Example B-40 compound B-10 6.7 45.3 Example B-41 compound B-11 6.7 45.1 Example B-42 compound B-12 6.65 42.6 Example B-43 compound B-13 6.7 41.3 Example B-44 compound B-14 6.65 42.1 Example B-45 compound B-15 6.6 41.9 Example B-46 Compound B-16 6.6 42.1 Example B-47 compound B-17 6.7 44.8 Example B-48 compound B-18 6.9 47.5 Example B-49 compound B-19 6.8 41.5 Example B-50 compound B-20 6.8 41.9 Example B-51 compound B-21 6.7 42.4 Example B-52 compound C-1 6.85 42.3 Example B-53 compound C-2 6.8 45.2 Example B-54 compound C-3 6.8 44.6 Example B-55 compound C-4 6.85 44.1 Example B-56 compound C-5 6.9 43.6 Example B-57 compound C-6 6.95 42.6 Example B-58 compound C-7 6.8 44.1 Example B-59 compound C-8 6.9 42.8 Example B-60 compound C-9 6.8 41.4 Example B-61 compound C-10 6.7 41.8 Example B-62 compound C-11 6.65 45.3 Example B-63 compound C-12 6.7 45.1 Example B-64 compound C-13 6.9 42.6 Example B-65 compound C-14 6.8 41.3 Example B-66 compound C-15 6.7 42.1 Example B-67 compound C-16 6.7 44.6 Example B-68 compound C-17 6.65 42.6 Example B-69 compound C-18 6.7 41.8 Example B-70 compound C-19 6.65 45.3 Example B-71 compound C-20 6.6 45.2 Example B-72 compound C-21 6.6 42.7 Example B-73 compound D-01 6.7 41.9 Example B-74 compound D-02 6.85 42.1 Example B-75 compound D-03 6.8 44.8 Example B-76 compound D-04 6.8 47.5 Example B-77 compound D-05 6.85 41.5 Example B-78 compound D-06 6.9 41.9 Example B-79 compound D-07 6.95 42.4 Example B-80 compound D-08 6.8 42.3 Example B-81 compound D-09 6.9 45.2 Example B-82 compound D-10 6.8 44.6 Example B-83 compound D-11 6.7 44.1 Example B-84 compound D-12 6.65 43.6 Example B-85 compound D-13 6.7 42.6 Example B-86 compound D-14 6.9 44.1 Example B-87 compound D-15 6.8 42.8 Example B-88 compound D-16 6.7 41.4 Example B-89 compound D-17 6.7 41.8 Example B-90 compound D-18 6.65 45.3 Example B-91 compound D-19 6.7 45.1 Example B-92 compound D-20 6.65 42.6 Example B-93 compound D-21 6.6 41.3 Example B-94 compound D-22 6.6 42.1 Example B-95 compound D-23 6.7 41.9 Example B-96 compound D-24 6.9 42.1 Example B-97 compound D-25 6.8 44.8 Example B-98 compound D-26 6.8 47.5 Example B-99 compound D-27 6.85 41.5 Example B-100 compound D-28 6.85 41.9 Example B-101 compound D-29 6.65 42.4 Example B-102 compound D-30 6.6 42.3 Example B-103 compound E-1 6.7 45.2 Example B-104 compound E-2 6.85 44.6 Example B-105 compound E-3 6.7 44.1 Example B-106 compound E-4 6.8 43.6 Example B-107 compound E-5 6.75 42.6 Example B-108 compound E-6 6.8 44.1 Example B-109 compound E-7 6.8 42.8 Example B-110 compound E-8 6.85 41.4 Example B-111 compound E-9 6.9 41.8 Example B-112 compound E-10 6.7 45.3 Example B-113 compound E-11 6.7 45.1 Example B-114 Compound E-12 6.65 42.6 Example B-115 compound E-13 6.7 41.3 Example B-116 compound E-14 6.65 42.1 Example B-117 Compound E-15 6.6 41.9 Example B-118 Compound E-16 6.6 42.1 Example B-119 compound E-17 6.7 44.8 Example B-120 compound E-18 6.9 47.5 Example B-121 compound E-19 6.8 41.5 Example B-122 compound E-20 6.8 41.9 Example B-123 Compound E-21 6.7 42.4 Example B-124 compound E-22 6.85 42.3 Example B-125 compound E-23 6.8 45.2 Example B-126 Compound E-24 6.8 44.6 Example B-127 compound E-25 6.85 44.1 Example B-128 compound E-26 6.9 43.6 Example B-129 Compound E-27 6.95 42.6 Example B-130 compound F-1 6.8 44.1 Example B-131 compound F-2 6.9 42.8 Example B-132 compound F-3 6.8 41.4 Example B-133 compound F-4 6.7 41.8 Example B-134 compound F-5 6.65 45.3 Example B-135 compound F-6 6.7 45.1 Example B-136 compound F-7 6.9 42.6 Example B-137 compound F-8 6.8 41.3 Example B-138 compound F-9 6.7 42.1 Example B-139 compound F-10 6.7 44.6 Example B-140 compound F-11 6.65 42.6 Example B-141 compound F-12 6.7 41.8 Example B-142 compound F-13 6.65 45.3 Example B-143 compound F-14 6.6 45.2 Example B-144 compound F-15 6.6 42.7 Example B-145 compound F-16 6.7 41.9 Example B-146 compound F-17 6.85 42.1 Example B-147 compound F-18 6.8 44.8 Example B-148 compound F-19 6.8 47.5 Example B-149 compound F-20 6.85 41.5 Example B-150 compound F-21 6.9 41.9 Example B-151 compound F-22 6.95 42.4 Example B-152 compound F-23 6.8 42.3 Example B-153 compound F-24 6.9 45.2 Example B-154 compound F-25 6.8 44.6 Example B-155 compound F-26 6.7 44.1 Example B-156 compound F-27 6.65 43.6 Example B-157 compound F-28 6.7 42.6 Example B-158 compound F-29 6.9 44.1 Example B-159 compound F-30 6.8 42.8 Example B-160 compound G-1 6.7 41.4 Example B-161 compound G-2 6.7 41.8 Example B-162 compound G-3 6.65 45.3 Example B-163 compound G-4 6.7 45.1 Example B-164 compound G-5 6.65 42.6 Example B-165 compound G-6 6.6 41.3 Example B-166 compound G-7 6.6 42.1 Example B-167 compound G-8 6.7 41.9 Example B-168 compound G-9 6.9 42.1 Example B-169 compound G-10 6.8 44.8 Example B-170 compound G-11 6.8 47.5 Example B-171 compound G-12 6.85 41.5 Example B-172 compound G-13 6.85 41.9 Example B-173 compound G-14 6.65 42.4 Example B-174 compound G-15 6.6 42.3 Example B-175 compound G-16 6.7 45.2 Example B-176 compound G-17 6.85 44.6 Example B-177 compound G-18 6.7 44.1 Example B-178 compound G-19 6.8 43.6 Example B-179 compound G-20 6.75 42.6 Example B-180 compound G-21 6.8 44.1 Example B-181 compound G-22 6.8 42.8 Example B-182 compound G-23 6.85 41.4 Example B-183 compound G-24 6.9 41.8 Example B-184 compound G-25 6.7 45.3 Example B-185 compound G-26 6.7 45.1 Example B-186 compound G-27 6.65 42.6 Example B-187 compound H-1 6.7 41.3 Example B-188 compound H-2 6.65 42.1 Example B-189 compound H-3 6.6 41.9 Example B-190 compound H-4 6.6 42.1 Example B-191 compound H-5 6.7 44.8 Example B-192 compound H-6 6.9 47.5 Example B-193 compound H-7 6.8 41.5 Example B-194 compound H-8 6.8 41.9 Example B-195 compound H-9 6.7 42.4 Example B-196 compound H-10 6.85 42.3 Example B-197 compound H-11 6.8 45.2 Example B-198 compound H-12 6.8 44.6 Example B-199 compound H-13 6.85 44.1 Example B-200 compound H-14 6.9 43.6 Example B-201 compound H-15 6.95 42.6 Example B-202 compound H-16 6.8 44.1 Example B-203 compound H-17 6.9 42.8 Example B-204 compound H-18 6.8 41.4 Example B-205 compound H-19 6.7 41.8 Example B-206 compound H-20 6.65 45.3 Example B-207 compound H-21 6.7 45.1 Example B-208 compound H-22 6.9 42.6 Example B-209 compound H-23 6.8 41.3 Example B-210 compound H-24 6.7 42.1 Example B-211 compound I-1 6.7 44.6 Example B-212 compound I-2 6.65 42.6 Example B-213 compound I-3 6.7 41.8 Example B-214 compound I-4 6.65 45.3 Example B-215 compound I-5 6.6 45.2 Example B-216 compound I-6 6.6 42.7 Example B-217 compound I-7 6.7 41.9 Example B-218 compound I-8 6.85 42.1 Example B-219 compound I-9 6.8 44.8 Example B-220 compound I-10 6.8 47.5 Example B-221 compound I-11 6.85 41.5 Example B-222 compound I-12 6.9 41.9 Example B-223 compound I-13 6.95 42.4 Example B-224 compound I-14 6.8 42.3 Example B-225 compound I-15 6.9 45.2 Example B-226 compound I-16 6.8 44.6 Example B-227 compound I-17 6.7 44.1 Example B-228 compound I-18 6.65 43.6 Example B-229 compound I-19 6.7 42.6 Example B-230 compound I-20 6.9 44.1 Example B-231 compound I-21 6.8 42.8 Example B-232 compound I-22 6.7 41.4 Example B-233 compound I-23 6.7 41.8 Example B-234 compound I-24 6.65 45.3 Example B-235 compound J-1 6.7 45.1 Example B-236 compound J-2 6.65 42.6 Example B-237 compound J-3 6.6 41.3 Example B-238 compound J-4 6.6 42.1 Example B-239 compound J-5 6.7 41.9 Example B-240 compound J-6 6.9 42.1 Example B-241 compound J-7 6.8 44.8 Example B-242 compound J-8 6.8 47.5 Example B-243 compound J-9 6.85 41.5 Example B-244 compound J-10 6.85 41.9 Example B-245 compound J-11 6.65 42.4 Example B-246 compound J-12 6.6 42.3 Example B-247 compound J-13 6.7 45.2 Example B-248 compound J-14 6.85 44.6 Example B-249 compound J-15 6.7 44.1 Example B-250 compound J-16 6.8 43.6 Example B-251 compound J-17 6.75 42.6 Example B-252 compound J-18 6.8 44.1 Example B-253 compound J-19 6.8 42.8 Example B-254 compound J-20 6.85 41.4 Example B-255 compound J-21 6.9 41.8 Example B-256 compound J-22 6.7 45.3 Example B-257 compound J-23 6.7 45.1 Example B-258 compound J-24 6.65 42.6 Example B-259 compound K-1 6.7 41.3 Example B-260 compound K-2 6.65 42.1 Example B-261 compound K-3 6.6 41.9 Example B-262 compound K-4 6.6 42.1 Example B-263 compound K-5 6.7 44.8 Example B-264 compound K-6 6.9 47.5 Example B-265 compound K-7 6.8 41.5 Example B-266 compound K-8 6.8 41.9 Example B-267 compound K-9 6.7 42.4 Example B-268 compound K-10 6.85 42.3 Example B-269 compound K-11 6.8 45.2 Example B-270 compound K-12 6.8 44.6 Example B-271 compound K-13 6.85 44.1 Example B-272 compound K-14 6.9 43.6 Example B-273 compound K-15 6.95 42.6 Example B-274 compound K-16 6.8 44.1 Example B-275 compound K-17 6.9 42.8 Example B-276 compound K-18 6.8 41.4 Example B-277 compound K-19 6.7 41.8 Example B-278 compound K-20 6.65 45.3 Example B-279 compound K-21 6.7 45.1 Example B-280 compound K-22 6.9 42.6 Example B-281 compound K-23 6.8 41.3 Example B-282 compound K-24 6.7 42.1 Example B-283 compound L-1 6.7 44.6 Example B-284 compound L-2 6.65 42.6 Example B-285 compound L-3 6.7 41.8 Example B-286 compound L-4 6.65 45.3 Example B-287 compound L-5 6.6 45.2 Example B-288 compound L-6 6.6 42.7 Example B-289 compound L-7 6.6 42.1 Example B-290 compound L-8 6.7 44.8 Example B-291 compound L-9 6.9 47.5 Example B-292 compound L-10 6.8 41.5 Example B-293 compound L-11 6.8 41.9 Example B-294 compound L-12 6.7 42.4 Example B-295 compound L-13 6.85 42.3 Example B-296 compound L-14 6.8 45.2 Example B-297 compound L-15 6.8 44.6 Example B-298 compound L-16 6.85 44.1 Example B-299 compound L-17 6.9 43.6 Example B-300 compound L-18 6.95 42.6 Example B-301 compound L-19 6.8 44.1 Example B-302 compound L-20 6.9 42.8 Example B-303 compound L-21 6.8 41.4 Example B-304 compound L-22 6.7 41.8 Example B-305 compound L-23 6.65 45.3 Example B-306 compound L-24 6.7 45.1 Example B-307 compound L-1 6.9 42.6 Example B-308 compound L-2 6.8 41.3 Example B-309 compound L-3 6.7 42.1 Example B-310 compound L-4 6.7 44.6 Example B-311 compound L-5 6.65 42.6 Example B-312 compound L-6 6.7 41.8 Example B-313 compound L-7 6.65 45.3 Example B-314 compound L-8 6.6 45.2 Example B-315 compound L-9 6.6 42.7 Example B-316 compound L-10 6.65 42.6 Example B-317 compound L-11 6.7 41.3 Example B-318 compound L-12 6.65 42.1 Example B-319 compound L-13 6.6 41.9 Example B-320 compound L-14 6.6 42.1 Example B-321 compound L-15 6.7 44.8 Example B-322 compound L-16 6.9 47.5 Example B-323 compound L-17 6.8 41.5 Example B-324 compound L-18 6.8 41.9 Example B-325 compound L-19 6.7 42.4 Example B-326 compound L-20 6.85 42.3 Example B-327 compound L-21 6.8 45.2 Example B-328 compound L-22 6.8 44.6 Example B-329 compound L-23 6.85 44.1 Example B-330 compound L-24 6.95 42.6 Comparative Example 2 - 6.93 38.2

As shown in Table 2, the green organic electroluminescent device (the green organic electroluminescent device prepared in Examples B-1 to B-330, respectively) using the compound represented by Formula 1 according to the present invention as a light emitting material, It was found that the conventional green organic electroluminescent device (the organic electroluminescent device of Comparative Example 2) using only CBP as a material for the light emitting layer exhibited better performance in terms of current efficiency and driving voltage.

[Examples C-1 to C-330] Preparation of red organic electroluminescent device

After high-purity sublimation purification of the compound synthesized in Synthesis Example by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.

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

On the ITO transparent electrode prepared as above, each compound of m-MTDATA (60 nm)/TCTA (80 nm)/A-1 to M-24 (40 nm)/CBP + 10% (piq)2Ir(acac) ( 30 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device.

The structures of m-MTDATA, TCTA, (piq)2Ir(acac) and CBP used are as follows.

[Comparative Example 3] Preparation of a red organic electroluminescent device

A red organic electroluminescent device was prepared in the same manner as in Example C-1, except that Compound A-1 was not used in Example C-1.

[Evaluation Example 3]

For the organic electroluminescent devices prepared in Examples C-1 to C-330, and Comparative Example 3, respectively, the driving voltage, current efficiency and emission peak at a current density of 10 mA/cm 2 were measured, and the results are shown in the table below 3 is shown.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example C-1 Compound A-1 4.9 11.9 Example C-2 compound A-2 5.1 12.1 Example C-3 compound A-3 5.0 14.8 Example C-4 Compound A-4 5.0 17.5 Example C-5 compound A-5 5.1 11.5 Example C-6 compound A-6 5.1 11.9 Example C-7 compound A-7 5.2 12.4 Example C-8 compound A-8 5.0 12.3 Example C-9 compound A-9 5.1 15.2 Example C-10 Compound A-10 5.0 14.6 Example C-11 Compound A-11 4.9 14.1 Example C-12 Compound A-12 4.9 13.6 Example C-13 compound A-13 4.9 12.6 Example C-14 Compound A-14 5.1 14.1 Example C-15 Compound A-15 5.0 12.8 Example C-16 Compound A-16 4.9 11.4 Example C-17 Compound A-17 4.9 11.8 Example C-18 Compound A-18 4.9 15.3 Example C-19 Compound A-19 4.9 15.1 Example C-20 Compound A-20 4.9 12.6 Example C-21 Compound A-21 4.8 11.3 Example C-22 Compound A-22 4.8 12.1 Example C-23 Compound A-23 4.9 11.9 Example C-24 Compound A-24 5.1 12.1 Example C-25 Compound A-25 5.0 14.8 Example C-26 Compound A-26 5.0 17.5 Example C-27 Compound A-27 5.1 11.5 Example C-28 Compound A-28 5.1 11.9 Example C-29 Compound A-29 4.9 12.4 Example C-30 compound A-30 4.8 12.3 Example C-31 compound B-1 4.9 15.2 Example C-32 compound B-2 5.1 14.6 Example C-33 compound B-3 4.9 14.1 Example C-34 compound B-4 5.0 13.6 Example C-35 compound B-5 5.0 12.6 Example C-36 compound B-6 5.0 14.1 Example C-37 compound B-7 5.0 12.8 Example C-38 compound B-8 5.1 11.4 Example C-39 compound B-9 5.1 11.8 Example C-40 compound B-10 4.3 15.3 Example C-41 compound B-11 4.9 15.1 Example C-42 compound B-12 4.7 12.6 Example C-43 compound B-13 4.5 11.3 Example C-44 compound B-14 4.9 12.1 Example C-45 compound B-15 4.8 11.9 Example C-46 Compound B-16 4.8 12.1 Example C-47 compound B-17 4.9 14.8 Example C-48 compound B-18 5.1 17.5 Example C-49 compound B-19 5.0 11.5 Example C-50 compound B-20 5.0 11.9 Example C-51 compound B-21 4.9 12.4 Example C-52 compound C-1 5.1 12.3 Example C-53 compound C-2 5.0 15.2 Example C-54 compound C-3 5.0 14.6 Example C-55 compound C-4 5.1 14.1 Example C-56 compound C-5 5.1 13.6 Example C-57 compound C-6 5.2 12.6 Example C-58 compound C-7 5.0 14.1 Example C-59 compound C-8 5.1 12.8 Example C-60 compound C-9 5.0 11.4 Example C-61 compound C-10 4.9 11.8 Example C-62 compound C-11 4.9 15.3 Example C-63 compound C-12 4.9 15.1 Example C-64 compound C-13 5.1 12.6 Example C-65 compound C-14 5.0 11.3 Example C-66 compound C-15 4.9 12.1 Example C-67 compound C-16 4.9 14.6 Example C-68 compound C-17 4.9 12.6 Example C-69 compound C-18 4.9 11.8 Example C-70 compound C-19 4.9 15.3 Example C-71 compound C-20 4.8 15.2 Example C-72 compound C-21 4.8 12.7 Example C-73 compound D-01 4.9 11.9 Example C-74 compound D-02 5.1 12.1 Example C-75 compound D-03 5.0 14.8 Example C-76 compound D-04 5.0 17.5 Example C-77 compound D-05 5.1 11.5 Example C-78 compound D-06 5.1 11.9 Example C-79 compound D-07 5.2 12.4 Example C-80 compound D-08 5.0 12.3 Example C-81 compound D-09 5.1 15.2 Example C-82 compound D-10 5.0 14.6 Example C-83 compound D-11 4.9 14.1 Example C-84 compound D-12 4.9 13.6 Example C-85 compound D-13 4.9 12.6 Example C-86 compound D-14 5.1 14.1 Example C-87 compound D-15 5.0 12.8 Example C-88 compound D-16 4.9 11.4 Example C-89 compound D-17 4.9 11.8 Example C-90 compound D-18 4.9 15.3 Example C-91 compound D-19 4.9 15.1 Example C-92 compound D-20 4.9 12.6 Example C-93 compound D-21 4.8 11.3 Example C-94 compound D-22 4.8 12.1 Example C-95 compound D-23 4.9 11.9 Example C-96 compound D-24 5.1 12.1 Example C-97 compound D-25 5.0 14.8 Example C-98 compound D-26 5.0 17.5 Example C-99 compound D-27 5.1 11.5 Example C-100 compound D-28 5.1 11.9 Example C-101 compound D-29 4.9 12.4 Example C-102 compound D-30 4.8 12.3 Example C-103 compound E-1 4.9 15.2 Example C-104 compound E-2 5.1 14.6 Example C-105 compound E-3 4.9 14.1 Example C-106 compound E-4 5.0 13.6 Example C-107 compound E-5 5.0 12.6 Example C-108 compound E-6 5.0 14.1 Example C-109 compound E-7 5.0 12.8 Example C-110 compound E-8 5.1 11.4 Example C-111 compound E-9 5.1 11.8 Example C-112 compound E-10 4.3 15.3 Example C-113 compound E-11 4.9 15.1 Example C-114 Compound E-12 4.7 12.6 Example C-115 compound E-13 4.5 11.3 Example C-116 compound E-14 4.9 12.1 Example C-117 Compound E-15 4.8 11.9 Example C-118 Compound E-16 4.8 12.1 Example C-119 compound E-17 4.9 14.8 Example C-120 compound E-18 5.1 17.5 Example C-121 compound E-19 5.0 11.5 Example C-122 compound E-20 5.0 11.9 Example C-123 Compound E-21 4.9 12.4 Example C-124 compound E-22 5.1 12.3 Example C-125 compound E-23 5.0 15.2 Example C-126 Compound E-24 5.0 14.6 Example C-127 compound E-25 5.1 14.1 Example C-128 compound E-26 5.1 13.6 Example C-129 Compound E-27 5.2 12.6 Example C-130 compound F-1 5.0 14.1 Example C-131 compound F-2 5.1 12.8 Example C-132 compound F-3 5.0 11.4 Example C-133 compound F-4 4.9 11.8 Example C-134 compound F-5 4.9 15.3 Example C-135 compound F-6 4.9 15.1 Example C-136 compound F-7 5.1 12.6 Example C-137 compound F-8 5.0 11.3 Example C-138 compound F-9 4.9 12.1 Example C-139 compound F-10 4.9 14.6 Example C-140 compound F-11 4.9 12.6 Example C-141 compound F-12 4.9 11.8 Example C-142 compound F-13 4.9 15.3 Example C-143 compound F-14 4.8 15.2 Example C-144 compound F-15 4.8 12.7 Example C-145 compound F-16 4.9 11.9 Example C-146 compound F-17 5.1 12.1 Example C-147 compound F-18 5.0 14.8 Example C-148 compound F-19 5.0 17.5 Example C-149 compound F-20 5.1 11.5 Example C-150 compound F-21 5.1 11.9 Example C-151 compound F-22 5.2 12.4 Example C-152 compound F-23 5.0 12.3 Example C-153 compound F-24 5.1 15.2 Example C-154 compound F-25 5.0 14.6 Example C-155 compound F-26 4.9 14.1 Example C-156 compound F-27 4.9 13.6 Example C-157 compound F-28 4.9 12.6 Example C-158 compound F-29 5.1 14.1 Example C-159 compound F-30 5.0 12.8 Example C-160 compound G-1 4.9 11.4 Example C-161 compound G-2 4.9 11.8 Example C-162 compound G-3 4.9 15.3 Example C-163 compound G-4 4.9 15.1 Example C-164 compound G-5 4.9 12.6 Example C-165 compound G-6 4.8 11.3 Example C-166 compound G-7 4.8 12.1 Example C-167 compound G-8 4.9 11.9 Example C-168 compound G-9 5.1 12.1 Example C-169 compound G-10 5.0 14.8 Example C-170 compound G-11 5.0 17.5 Example C-171 compound G-12 5.1 11.5 Example C-172 compound G-13 5.1 11.9 Example C-173 compound G-14 4.9 12.4 Example C-174 compound G-15 4.8 12.3 Example C-175 compound G-16 4.9 15.2 Example C-176 compound G-17 5.1 14.6 Example C-177 compound G-18 4.9 14.1 Example C-178 compound G-19 5.0 13.6 Example C-179 compound G-20 5.0 12.6 Example C-180 compound G-21 5.0 14.1 Example C-181 compound G-22 5.0 12.8 Example C-182 compound G-23 5.1 11.4 Example C-183 compound G-24 5.1 11.8 Example C-184 compound G-25 4.3 15.3 Example C-185 compound G-26 4.9 15.1 Example C-186 compound G-27 4.7 12.6 Example C-187 compound H-1 4.5 11.3 Example C-188 compound H-2 4.9 12.1 Example C-189 compound H-3 4.8 11.9 Example C-190 compound H-4 4.8 12.1 Example C-191 compound H-5 4.9 14.8 Example C-192 compound H-6 5.1 17.5 Example C-193 compound H-7 5.0 11.5 Example C-194 compound H-8 5.0 11.9 Example C-195 compound H-9 4.9 12.4 Example C-196 compound H-10 5.1 12.3 Example C-197 compound H-11 5.0 15.2 Example C-198 compound H-12 5.0 14.6 Example C-199 compound H-13 5.1 14.1 Example C-200 compound H-14 5.1 13.6 Example C-201 compound H-15 5.2 12.6 Example C-202 compound H-16 5.0 14.1 Example C-203 compound H-17 5.1 12.8 Example C-204 compound H-18 5.0 11.4 Example C-205 compound H-19 4.9 11.8 Example C-206 compound H-20 4.9 15.3 Example C-207 compound H-21 4.9 15.1 Example C-208 compound H-22 5.1 12.6 Example C-209 compound H-23 5.0 11.3 Example C-210 compound H-24 4.9 12.1 Example C-211 compound I-1 4.9 14.6 Example C-212 compound I-2 4.9 12.6 Example C-213 compound I-3 4.9 11.8 Example C-214 compound I-4 4.9 15.3 Example C-215 compound I-5 4.8 15.2 Example C-216 compound I-6 4.8 12.7 Example C-217 compound I-7 4.9 11.9 Example C-218 compound I-8 5.1 12.1 Example C-219 compound I-9 5.0 14.8 Example C-220 compound I-10 5.0 17.5 Example C-221 compound I-11 5.1 11.5 Example C-222 compound I-12 5.1 11.9 Example C-223 compound I-13 5.2 12.4 Example C-224 compound I-14 5.0 12.3 Example C-225 compound I-15 5.1 15.2 Example C-226 compound I-16 5.0 14.6 Example C-227 compound I-17 4.9 14.1 Example C-228 compound I-18 4.9 13.6 Example C-229 compound I-19 4.9 12.6 Example C-230 compound I-20 5.1 14.1 Example C-231 compound I-21 5.0 12.8 Example C-232 compound I-22 4.9 11.4 Example C-233 compound I-23 4.9 11.8 Example C-234 compound I-24 4.9 15.3 Example C-235 compound J-1 4.9 15.1 Example C-236 compound J-2 4.9 12.6 Example C-237 compound J-3 4.8 11.3 Example C-238 compound J-4 4.8 12.1 Example C-239 compound J-5 4.9 11.9 Example C-240 compound J-6 5.1 12.1 Example C-241 compound J-7 5.0 14.8 Example C-242 compound J-8 5.0 17.5 Example C-243 compound J-9 5.1 11.5 Example C-244 compound J-10 5.1 11.9 Example C-245 compound J-11 4.9 12.4 Example C-246 compound J-12 4.8 12.3 Example C-247 compound J-13 4.9 15.2 Example C-248 compound J-14 5.1 14.6 Example C-249 compound J-15 4.9 14.1 Example C-250 compound J-16 5.0 13.6 Example C-251 compound J-17 5.0 12.6 Example C-252 compound J-18 5.0 14.1 Example C-253 compound J-19 5.0 12.8 Example C-254 compound J-20 5.1 11.4 Example C-255 compound J-21 5.1 11.8 Example C-256 compound J-22 4.3 15.3 Example C-257 compound J-23 4.9 15.1 Example C-258 compound J-24 4.7 12.6 Example C-259 compound K-1 4.5 11.3 Example C-260 compound K-2 4.9 12.1 Example C-261 compound K-3 4.8 11.9 Example C-262 compound K-4 4.8 12.1 Example C-263 compound K-5 4.9 14.8 Example C-264 compound K-6 5.1 17.5 Example C-265 compound K-7 5.0 11.5 Example C-266 compound K-8 5.0 11.9 Example C-267 compound K-9 4.9 12.4 Example C-268 compound K-10 5.1 12.3 Example C-269 compound K-11 5.0 15.2 Example C-270 compound K-12 5.0 14.6 Example C-271 compound K-13 5.1 14.1 Example C-272 compound K-14 5.1 13.6 Example C-273 compound K-15 5.2 12.6 Example C-274 compound K-16 5.0 14.1 Example C-275 compound K-17 5.1 12.8 Example C-276 compound K-18 5.0 11.4 Example C-277 compound K-19 4.9 11.8 Example C-278 compound K-20 4.9 15.3 Example C-279 compound K-21 4.9 15.1 Example C-280 compound K-22 5.1 12.6 Example C-281 compound K-23 5.0 11.3 Example C-282 compound K-24 4.9 12.1 Example C-283 compound L-1 4.9 14.6 Example C-284 compound L-2 4.9 12.6 Example C-285 compound L-3 4.9 11.8 Example C-286 compound L-4 4.9 15.3 Example C-287 compound L-5 4.8 15.2 Example C-288 compound L-6 4.8 12.7 Example C-289 compound L-7 5.0 11.3 Example C-290 compound L-8 5.1 11.8 Example C-291 compound L-9 4.3 15.3 Example C-292 compound L-10 4.9 15.1 Example C-293 compound L-11 4.7 12.6 Example C-294 compound L-12 4.5 11.3 Example C-295 compound L-13 4.9 12.1 Example C-296 compound L-14 4.8 11.9 Example C-297 compound L-15 4.8 12.1 Example C-298 compound L-16 4.9 14.8 Example C-299 compound L-17 5.1 17.5 Example C-300 compound L-18 5.0 11.5 Example C-301 compound L-19 5.0 11.9 Example C-302 compound L-20 4.9 12.4 Example C-303 compound L-21 5.1 12.3 Example C-304 compound L-22 5.0 15.2 Example C-305 compound L-23 5.0 14.6 Example C-306 compound L-24 5.1 14.1 Example C-307 compound L-1 5.1 13.6 Example C-308 compound L-2 5.2 12.6 Example C-309 compound L-3 5.0 14.1 Example C-310 compound L-4 5.1 12.8 Example C-311 compound L-5 5.0 11.4 Example C-312 compound L-6 4.9 11.8 Example C-313 compound L-7 4.9 15.3 Example C-314 compound L-8 4.9 15.1 Example C-315 compound L-9 5.1 12.6 Example C-316 compound L-10 5.0 11.3 Example C-317 compound L-11 4.9 12.1 Example C-318 compound L-12 4.9 14.6 Example C-319 compound L-13 4.9 12.6 Example C-320 compound L-14 4.9 11.8 Example C-321 compound L-15 4.9 15.3 Example C-322 compound L-16 4.8 15.2 Example C-323 compound L-17 4.8 12.7 Example C-324 compound L-18 5.0 11.5 Example C-325 compound L-19 5.0 11.9 Example C-326 compound L-20 4.9 12.4 Example C-327 compound L-21 5.1 12.3 Example C-328 compound L-22 5.0 15.2 Example C-329 compound L-23 5.0 14.6 Example C-330 compound L-24 5.1 14.1 Comparative Example 3 - 5.2 8.2

As shown in Table 3, the red organic electroluminescent device (the red organic electroluminescent device prepared in Examples C-1 to C-330, respectively) using the compound represented by Formula 1 according to the present invention as a light emitting material, It was found that compared to the conventional red organic electroluminescent device (the organic electroluminescent device of Comparative Example 3) using only CBP as a material for the light emitting layer, it showed better performance in terms of current efficiency and driving voltage.

[Example D-1 to D-330] Preparation of blue organic electroluminescent device

After high-purity sublimation purification of the compound synthesized in Synthesis Example by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.

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

On the ITO transparent electrode prepared as above, DS-205 (Doosan) (80 nm) / NPB (15 nm) / each compound of A-1 to M-24 (15 nm) / ADN + 5% DS-405 ( Doosan Co.) (30 nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) were stacked in the order to prepare an organic electroluminescent device.

The structure of the ADN used is as follows.

[Comparative Example 4] Fabrication of a blue organic electroluminescent device

A blue organic electroluminescent device was manufactured in the same manner as in Example D-1, except that A-1 was not used in Example D-1.

[Evaluation Example 4]

For each of the blue organic electroluminescent devices manufactured in Examples C-1 to C-330 and Comparative Example 4, the driving voltage and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 4 below. It was.

Sample hole transport layer Driving voltage (V) Current efficiency (cd/A) Example D-1 Compound A-1 4.3 9.2 Example D-2 compound A-2 4.5 7.1 Example D-3 compound A-3 4.6 8.3 Example D-4 Compound A-4 4.2 9.6 Example D-5 compound A-5 4.7 6.5 Example D-6 compound A-6 4.9 7.1 Example D-7 compound A-7 4.5 8.6 Example D-8 compound A-8 4.7 7.5 Example D-9 compound A-9 4.9 7.6 Example D-10 Compound A-10 4.6 8.6 Example D-11 Compound A-11 5.2 7.1 Example D-12 Compound A-12 5.3 5.6 Example D-13 compound A-13 4.5 9 Example D-14 Compound A-14 4.8 8.2 Example D-15 Compound A-15 4.7 8.2 Example D-16 Compound A-16 4.6 9.3 Example D-17 Compound A-17 5.3 5.3 Example D-18 Compound A-18 5.2 5.9 Example D-19 Compound A-19 4.7 8.7 Example D-20 Compound A-20 4.9 8.2 Example D-21 Compound A-21 5.0 7.8 Example D-22 Compound A-22 4.7 8.4 Example D-23 Compound A-23 5.3 5.2 Example D-24 Compound A-24 5.3 5.5 Example D-25 Compound A-25 4.5 9.3 Example D-26 Compound A-26 4.8 8.4 Example D-27 Compound A-27 5.0 8.6 Example D-28 Compound A-28 4.4 9.5 Example D-29 Compound A-29 4.9 7.6 Example D-30 compound A-30 4.8 7.2 Example D-31 compound B-1 4.4 9.1 Example D-32 compound B-2 4.8 8.2 Example D-33 compound B-3 5.0 7 Example D-34 compound B-4 4.4 9.3 Example D-35 compound B-5 5.0 8.8 Example D-36 compound B-6 5.2 6.2 Example D-37 compound B-7 4.7 7.3 Example D-38 compound B-8 5.3 5.5 Example D-39 compound B-9 5.1 7.3 Example D-40 compound B-10 5.0 7.8 Example D-41 compound B-11 4.4 8.4 Example D-42 compound B-12 4.9 5.2 Example D-43 compound B-13 4.8 5.5 Example D-44 compound B-14 4.4 9.3 Example D-45 compound B-15 4.8 8.4 Example D-46 Compound B-16 5.0 8.6 Example D-47 compound B-17 4.4 9.5 Example D-48 compound B-18 5.0 7.6 Example D-49 compound B-19 5.0 7 Example D-50 compound B-20 4.4 9.3 Example D-51 compound B-21 5.0 8.8 Example D-52 compound C-1 5.2 6.2 Example D-53 compound C-2 4.7 7.3 Example D-54 compound C-3 5.3 5.5 Example D-55 compound C-4 5.1 7.3 Example D-56 compound C-5 5.0 7.8 Example D-57 compound C-6 4.4 8.4 Example D-58 compound C-7 4.9 5.2 Example D-59 compound C-8 4.8 5.5 Example D-60 compound C-9 4.4 9.3 Example D-61 compound C-10 4.8 8.4 Example D-62 compound C-11 5.0 8.6 Example D-63 compound C-12 4.4 9.5 Example D-64 compound C-13 5.0 7.6 Example D-65 compound C-14 5.2 7.2 Example D-66 compound C-15 4.7 7.8 Example D-67 compound C-16 4.7 7.3 Example D-68 compound C-17 5.3 5.5 Example D-69 compound C-18 5.1 7.3 Example D-70 compound C-19 5.0 7.8 Example D-71 compound C-20 4.4 8.4 Example D-72 compound C-21 4.9 5.2 Example D-73 compound D-01 4.3 9.2 Example D-74 compound D-02 4.5 7.1 Example D-75 compound D-03 4.6 8.3 Example D-76 compound D-04 4.2 9.6 Example D-77 compound D-05 4.7 6.5 Example D-78 compound D-06 4.9 7.1 Example D-79 compound D-07 4.5 8.6 Example D-80 compound D-08 4.7 7.5 Example D-81 compound D-09 4.9 7.6 Example D-82 compound D-10 4.6 8.6 Example D-83 compound D-11 5.2 7.1 Example D-84 compound D-12 5.3 5.6 Example D-85 compound D-13 4.5 9 Example D-86 compound D-14 4.8 8.2 Example D-87 compound D-15 4.7 8.2 Example D-88 compound D-16 4.6 9.3 Example D-89 compound D-17 5.3 5.3 Example D-90 compound D-18 5.2 5.9 Example D-91 compound D-19 4.7 8.7 Example D-92 compound D-20 4.9 8.2 Example D-93 compound D-21 5.0 7.8 Example D-94 compound D-22 4.7 8.4 Example D-95 compound D-23 5.3 5.2 Example D-96 compound D-24 5.3 5.5 Example D-97 compound D-25 4.5 9.3 Example D-98 compound D-26 4.8 8.4 Example D-99 compound D-27 5.0 8.6 Example D-100 compound D-28 4.4 9.5 Example D-101 compound D-29 4.9 7.6 Example D-102 compound D-30 4.8 7.2 Example D-103 compound E-1 4.4 9.1 Example D-104 compound E-2 4.8 8.2 Example D-105 compound E-3 5.0 7 Example D-106 compound E-4 4.4 9.3 Example D-107 compound E-5 5.0 8.8 Example D-108 compound E-6 5.2 6.2 Example D-109 compound E-7 4.7 7.3 Example D-110 compound E-8 5.3 5.5 Example D-111 compound E-9 5.1 7.3 Example D-112 compound E-10 5.0 7.8 Example D-113 compound E-11 4.4 8.4 Example D-114 Compound E-12 4.9 5.2 Example D-115 compound E-13 4.8 5.5 Example D-116 compound E-14 4.4 9.3 Example D-117 Compound E-15 4.8 8.4 Example D-118 Compound E-16 5.0 8.6 Example D-119 compound E-17 4.4 9.5 Example D-120 compound E-18 5.0 7.6 Example D-121 compound E-19 5.0 7 Example D-122 compound E-20 4.4 9.3 Example D-123 Compound E-21 5.0 8.8 Example D-124 compound E-22 5.2 6.2 Example D-125 compound E-23 4.7 7.3 Example D-126 Compound E-24 5.3 5.5 Example D-127 compound E-25 5.1 7.3 Example D-128 compound E-26 5.0 7.8 Example D-129 Compound E-27 4.4 8.4 Example D-130 compound F-1 4.9 5.2 Example D-131 compound F-2 4.8 5.5 Example D-132 compound F-3 4.4 9.3 Example D-133 compound F-4 4.8 8.4 Example D-134 compound F-5 5.0 8.6 Example D-135 compound F-6 4.4 9.5 Example D-136 compound F-7 5.0 7.6 Example D-137 compound F-8 5.2 7.2 Example D-138 compound F-9 4.7 7.8 Example D-139 compound F-10 4.7 7.3 Example D-140 compound F-11 5.3 5.5 Example D-141 compound F-12 5.1 7.3 Example D-142 compound F-13 5.0 7.8 Example D-143 compound F-14 4.4 8.4 Example D-144 compound F-15 4.9 5.2 Example D-145 compound F-16 4.3 9.2 Example D-146 compound F-17 4.5 7.1 Example D-147 compound F-18 4.6 8.3 Example D-148 compound F-19 4.2 9.6 Example D-149 compound F-20 4.7 6.5 Example D-150 compound F-21 4.9 7.1 Example D-151 compound F-22 4.5 8.6 Example D-152 compound F-23 4.7 7.5 Example D-153 compound F-24 4.9 7.6 Example D-154 compound F-25 4.6 8.6 Example D-155 compound F-26 5.2 7.1 Example D-156 compound F-27 5.3 5.6 Example D-157 compound F-28 4.5 9 Example D-158 compound F-29 4.8 8.2 Example D-159 compound F-30 4.7 8.2 Example D-160 compound G-1 4.6 9.3 Example D-161 compound G-2 5.3 5.3 Example D-162 compound G-3 5.2 5.9 Example D-163 compound G-4 4.7 8.7 Example D-164 compound G-5 4.9 8.2 Example D-165 compound G-6 5.0 7.8 Example D-166 compound G-7 4.7 8.4 Example D-167 compound G-8 5.3 5.2 Example D-168 compound G-9 5.3 5.5 Example D-169 compound G-10 4.5 9.3 Example D-170 compound G-11 4.8 8.4 Example D-171 compound G-12 5.0 8.6 Example D-172 compound G-13 4.4 9.5 Example D-173 compound G-14 4.9 7.6 Example D-174 compound G-15 4.8 7.2 Example D-175 compound G-16 4.4 9.1 Example D-176 compound G-17 4.8 8.2 Example D-177 compound G-18 5.0 7 Example D-178 compound G-19 4.4 9.3 Example D-179 compound G-20 5.0 8.8 Example D-180 compound G-21 5.2 6.2 Example D-181 compound G-22 4.7 7.3 Example D-182 compound G-23 5.3 5.5 Example D-183 compound G-24 5.1 7.3 Example D-184 compound G-25 5.0 7.8 Example D-185 compound G-26 4.4 8.4 Example D-186 compound G-27 4.9 5.2 Example D-187 compound H-1 4.8 5.5 Example D-188 compound H-2 4.4 9.3 Example D-189 compound H-3 4.8 8.4 Example D-190 compound H-4 5.0 8.6 Example D-191 compound H-5 4.4 9.5 Example D-192 compound H-6 5.0 7.6 Example D-193 compound H-7 5.0 7 Example D-194 compound H-8 4.4 9.3 Example D-195 compound H-9 5.0 8.8 Example D-196 compound H-10 5.2 6.2 Example D-197 compound H-11 4.7 7.3 Example D-198 compound H-12 5.3 5.5 Example D-199 compound H-13 5.1 7.3 Example D-200 compound H-14 5.0 7.8 Example D-201 compound H-15 4.4 8.4 Example D-202 compound H-16 4.9 5.2 Example D-203 compound H-17 4.8 5.5 Example D-204 compound H-18 4.4 9.3 Example D-205 compound H-19 4.8 8.4 Example D-206 compound H-20 5.0 8.6 Example D-207 compound H-21 4.4 9.5 Example D-208 compound H-22 5.0 7.6 Example D-209 compound H-23 5.2 7.2 Example D-210 compound H-24 4.7 7.8 Example D-211 compound I-1 4.7 7.3 Example D-212 compound I-2 5.3 5.5 Example D-213 compound I-3 5.1 7.3 Example D-214 compound I-4 5.0 7.8 Example D-215 compound I-5 4.4 8.4 Example D-216 compound I-6 4.9 5.2 Example D-217 compound I-7 4.3 9.2 Example D-218 compound I-8 4.5 7.1 Example D-219 compound I-9 4.6 8.3 Example D-220 compound I-10 4.2 9.6 Example D-221 compound I-11 4.7 6.5 Example D-222 compound I-12 4.9 7.1 Example D-223 compound I-13 4.5 8.6 Example D-224 compound I-14 4.7 7.5 Example D-225 compound I-15 4.9 7.6 Example D-226 compound I-16 4.6 8.6 Example D-227 compound I-17 5.2 7.1 Example D-228 compound I-18 5.3 5.6 Example D-229 compound I-19 4.5 9 Example D-230 compound I-20 4.8 8.2 Example D-231 compound I-21 4.7 8.2 Example D-232 compound I-22 4.6 9.3 Example D-233 compound I-23 5.3 5.3 Example D-234 compound I-24 5.2 5.9 Example D-235 compound J-1 4.7 8.7 Example D-236 compound J-2 4.9 8.2 Example D-237 compound J-3 5.0 7.8 Example D-238 compound J-4 4.7 8.4 Example D-239 compound J-5 5.3 5.2 Example D-240 compound J-6 5.3 5.5 Example D-241 compound J-7 4.5 9.3 Example D-242 compound J-8 4.8 8.4 Example D-243 compound J-9 5.0 8.6 Example D-244 compound J-10 4.4 9.5 Example D-245 compound J-11 4.9 7.6 Example D-246 compound J-12 4.8 7.2 Example D-247 compound J-13 4.4 9.1 Example D-248 compound J-14 4.8 8.2 Example D-249 compound J-15 5.0 7 Example D-250 compound J-16 4.4 9.3 Example D-251 compound J-17 5.0 8.8 Example D-252 compound J-18 5.2 6.2 Example D-253 compound J-19 4.7 7.3 Example D-254 compound J-20 5.3 5.5 Example D-255 compound J-21 5.1 7.3 Example D-256 compound J-22 5.0 7.8 Example D-257 compound J-23 4.4 8.4 Example D-258 compound J-24 4.9 5.2 Example D-259 compound K-1 4.8 5.5 Example D-260 compound K-2 4.4 9.3 Example D-261 compound K-3 4.8 8.4 Example D-262 compound K-4 5.0 8.6 Example D-263 compound K-5 4.4 9.5 Example D-264 compound K-6 5.0 7.6 Example D-265 compound K-7 5.0 7 Example D-266 compound K-8 4.4 9.3 Example D-267 compound K-9 5.0 8.8 Example D-268 compound K-10 5.2 6.2 Example D-269 compound K-11 4.7 7.3 Example D-270 compound K-12 5.3 5.5 Example D-271 compound K-13 5.1 7.3 Example D-272 compound K-14 5.0 7.8 Example D-273 compound K-15 4.4 8.4 Example D-274 compound K-16 4.9 5.2 Example D-275 compound K-17 4.8 5.5 Example D-276 compound K-18 4.4 9.3 Example D-277 compound K-19 4.8 8.4 Example D-278 compound K-20 5.0 8.6 Example D-279 compound K-21 4.4 9.5 Example D-280 compound K-22 5.0 7.6 Example D-281 compound K-23 5.2 7.2 Example D-282 compound K-24 4.7 7.8 Example D-283 compound L-1 4.7 7.3 Example D-284 compound L-2 5.3 5.5 Example D-285 compound L-3 5.1 7.3 Example D-286 compound L-4 5.0 7.8 Example D-287 compound L-5 4.4 8.4 Example D-288 compound L-6 4.9 5.2 Example D-289 compound L-7 5.2 6.2 Example D-290 compound L-8 4.7 7.3 Example D-291 compound L-9 5.3 5.5 Example D-292 compound L-10 5.1 7.3 Example D-293 compound L-11 5.0 7.8 Example D-294 compound L-12 4.4 8.4 Example D-295 compound L-13 4.9 5.2 Example D-296 compound L-14 4.8 5.5 Example D-297 compound L-15 4.4 9.3 Example D-298 compound L-16 4.8 8.4 Example D-299 compound L-17 5.0 8.6 Example D-300 compound L-18 4.4 9.5 Example D-301 compound L-19 5.0 7.6 Example D-302 compound L-20 5.0 7 Example D-303 compound L-21 4.4 9.3 Example D-304 compound L-22 5.0 8.8 Example D-305 compound L-23 5.2 6.2 Example D-306 compound L-24 4.7 7.3 Example D-307 compound L-1 5.3 5.5 Example D-308 compound L-2 5.1 7.3 Example D-309 compound L-3 5.0 7.8 Example D-310 compound L-4 4.4 8.4 Example D-311 compound L-5 4.9 5.2 Example D-312 compound L-6 4.8 5.5 Example D-313 compound L-7 4.4 9.3 Example D-314 compound L-8 4.8 8.4 Example D-315 compound L-9 5.0 8.6 Example D-316 compound L-10 4.4 9.5 Example D-317 compound L-11 5.0 7.6 Example D-318 compound L-12 5.2 7.2 Example D-319 compound L-13 4.7 7.8 Example D-320 compound L-14 5.2 6.2 Example D-321 compound L-15 4.7 7.3 Example D-322 compound L-16 5.3 5.5 Example D-323 compound L-17 5.1 7.3 Example D-324 compound L-18 5.0 7.8 Example D-325 compound L-19 4.4 8.4 Example D-326 compound L-20 4.9 5.2 Example D-327 compound L-21 4.8 5.5 Example D-328 compound L-22 4.4 9.3 Example D-329 compound L-23 4.8 8.4 Example D-330 compound L-24 5.0 8.6 Comparative Example 4 - 5.6 4.8

As shown in Table 4, the blue organic electroluminescent device (the blue organic electroluminescent device manufactured in Examples D-1 to D-330, respectively) using the compound represented by Formula 1 according to the present invention as a light emitting material, It was found that compared to the conventional blue organic electroluminescent device (the organic electroluminescent device of Comparative Example 4), it showed better performance in terms of current efficiency and driving voltage.

Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and detailed description of the invention, and this also falls within the scope of the invention. it is natural

Claims (12)

A compound represented by Formula 4 or Formula 5 below:
[Formula 4]

[Formula 5]

In Formula 4 or Formula 5,
A plurality of X ₁ are each independently selected from the group consisting of O, S, N(R ₆ ) and C(R ₇ )(R ₈ ), wherein the plurality of X ₁ are all N(R ₆ ) or all C( not R ₇ )(R ₈ );
R _{1 To} R ₈ are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₃ ~ C ₄₀ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C ₆ ~ C ₆₀ aryl group, heteroaryl group having 5 to 60 nuclear atoms, C ₁ ~ C ₄₀ alkyl Oxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ Alkyl boron group, C ₆ ~ C ₆₀ Aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl phosphine blood group and a C ₆ ~ C selected from the ₆₀ group consisting of an aryl amine of the or each of R ₄ and R adjacent ₅ combine with each other to form a condensed ring;
Ar ₄ and Ar ₅ 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, a heteroaryl group having 5 to 60 nuclear atoms, and a C ₆ ~ C _{60 arylamine group,} wherein Ar ₄ and Ar ₅ form a bond with each other;
L _{1 To} L ₃ are each independently selected from the group consisting of a single bond, a C ₆ ~ C ₁₈ arylene group, and a heteroarylene group having 5 to 18 nuclear atoms;
a and b are each independently an integer of 0 to 4,
The R _{1 To} R ₈ , Ar _{4 To} Ar ₅ Aryl group, heteroaryl group, and arylamine group, R _{1 To} R ₈ Alkyl group, cycloalkyl group, heterocycloalkyl group, alkyloxy group, aryloxy group, alkylsilyl group , arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group and mono or diaryl phosphinyl group, L ₁ to L ₃ arylene group, heteroarylene group is each independently, C ₁ ~ C ₄₀ Alkyl group, C ₂ ~ C ₄₀ Alkenyl group, C ₂ ~ C ₄₀ Alkynyl group, C ₃ ~ C ₄₀ Cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C ₆ ~ C ₆₀ Aryl group, the number of nuclear atoms 5 to 60 heteroaryl group, C ₁ ~ C ₄₀ Alkyloxy group, C ₆ ~ C ₆₀ Aryloxy group, C ₃ ~ C ₄₀ Alkylsilyl group, C ₆ ~ C ₆₀ Arylsilyl group, C ₁ ~ C ₄₀ alkyl boron group, C ₆ ~ C ₆₀ aryl boron group, C ₆ ~ C ₆₀ aryl phosphine group, C ₆ ~ C ₆₀ mono or diaryl Phosphinicosuccinic aryl group and a C ₆ ~ C ₆₀ amine When substituted with one or more selected from the group consisting of a group or unsubstituted, and substituted with a plurality of substituents, they are the same or different from each other.
(However, in Formulas 4 and 5, R ₄ and R ₅ are not heteroaryl) According to claim 1,
The L ₁ to L ₃ are each independently selected from the group consisting of a single bond, a phenylene group, a biphenylene group, a fluorenyl group, and a pyridinyl group. According to claim 1,
Ar ₄ and Ar ₅ are the same as or different from each other, and each independently represents a C ₆ ~ C ₁₈ aryl group or a heteroaryl group having 5 to 18 nuclear atoms. According to claim 1,
at least one of R ₄ and R ₅ forms a bond with _{L 1} or L _{2 .} delete delete According to claim 1,
R ₇ and R ₈ are each independently a methyl group or a phenyl group, or R ₇ and R ₈ are combined with each other to form a substituent represented by the following formula (7):
[Formula 7]

In Chemical Formula 7, * is a portion where a bond is formed. According to claim 1,
At least one of Ar ₄ and Ar ₅ is a compound characterized in that a substituent represented by the following formula (2):
[Formula 2]

In Formula 2, X ₁ , R ₄ to R ₅ and a to b are as defined in claim 1. delete According to claim 1,
The compound is a compound characterized in that it is selected from the group consisting of:

(i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode, wherein at least one of the at least one organic material layer is An organic electroluminescent device comprising the compound according to any one of claims 7 to 8 and 10. 12. The method of claim 11,
The organic material layer containing the compound is an organic electroluminescent device, characterized in that selected from the group consisting of a hole transport layer, an electron blocking layer and a light emitting auxiliary layer.