KR101298465B1 - Phenazine-based compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a phenazine-based compound having a specific structure and an organic electroluminescent device comprising the compound, specifically, by applying the phenazine-based compound as a phosphorescent light emitting layer material, luminous efficiency, brightness, power efficiency, thermal stability and device It is possible to provide an organic light emitting device having improved overall characteristics such as lifespan.

Description

Phenazine-based compound and organic electroluminescent device including the same {PHENAZINE-BASED COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME}

The present invention relates to a phenazine compound and an organic electroluminescent device comprising the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic EL device using an organic light emitting phenomenon typically has a structure including an anode, a cathode, and an organic material layer interposed therebetween. The organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.

When the voltage is applied between the two electrodes in the structure of the organic EL device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and the injected holes and electrons are recombined in the emission layer to exciton an electron-hole pair. To form. When an exciton with a structure in which the molecule's pi-electrons are excited falls back to the ground, it shines.

The material used as the organic material layer in the organic light emitting device may be classified into a light emitting layer material, a charge transport layer material, a hole injection layer material, a hole transport layer material, an electron transport layer material, an electron injection layer material and the like according to a function.

The light emitting layer material may be classified into a blue, green, and red light emitting layer material and yellow and orange light emitting layer materials necessary to realize a better natural color according to the light emitting color. In addition, in order to increase luminous efficiency through increase in color purity and energy transfer, a host / dopant system may be used as the light emitting layer material. The principle is that when a small amount of phosphorescent or fluorescent dye (hereinafter referred to as 'dopant') in the light emitting layer is mixed with a small amount of energy band gap and excellent luminous efficiency (hereinafter, referred to as 'dopant'), the excitons generated in the host are transferred to the dopant. It is a light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

In particular, the phosphorescent emission layer material may expect a 100% higher luminous effect than the fluorescent emission layer material, and thus may have a higher luminous efficiency than the fluorescent emission layer material having a luminous efficiency of 25%. However, the phosphorescent light emitting layer material currently has a slower development speed than the fluorescent light emitting layer material and has a short lifespan for application to a prototype.

In order to fully exhibit the excellent characteristics of the above-described organic EL device, the material constituting the organic material layer in the device, that is, the hole injection layer material, the hole transport layer material, the light emitting layer material, the electron transport layer material, the electron injection layer material, etc. Although support should be preceded, development of a stable and efficient organic material layer for an organic light emitting device has not been sufficiently achieved, and therefore, development of new materials is continuously required. In particular, there is a need for the development of more stable and efficient materials that can be used as light emitting layer materials.

The present invention to solve the above problems, to provide a compound that can improve the overall characteristics such as luminous efficiency, brightness, power efficiency, thermal stability and device life, and an organic electroluminescent device using the compound.

The present invention provides a compound represented by the following formula (1), preferably a phenazine-based compound.

In Formula 1,

Ar ₁ to Ar ₄ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, and C ₆ ~ C ₄₀ aromatic ring, or fused aliphatic ring, condensed aromatic ring with adjacent groups , A group capable of forming a condensed heteroaliphatic ring or a condensed heteroaromatic ring,

At least one of Ar ₁ to Ar ₄ is a C ₆ ~ C ₄₀ aromatic ring, or a group capable of forming a fused aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with an adjacent group ego;

X and Y are the same as or different from each other, each independently selected from the group consisting of NA ¹ , S and O, or Y may be directly connected,

A ¹ is hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl, C ₂ ~ C ₄₀ alkynyl, C ₅ ~ C ₄₀ aryl , C ₅ ~ C ₄₀ aryloxy, C ₁ ~ C ₄₀ alkyloxy, C ₅ ~ C ₄₀ arylamino, C ₅ ~ C ₄₀ diarylamino, (C ₅ ~ C ₄₀ aryl) C ₁ ~ C ₄₀ alkyl, C ₃ -C ₄₀ cycloalkyl, and heterocycloalkyl having 3 to 40 nuclear atoms;

Wherein R ₁ to R ₄ are the same or different, each independently represent hydrogen, deuterium, and C ₁ ~ C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl group, alkynyl of _{C 2 ~ C 40, C 5} ~ C to each other ₄₀ aryl, the number of nuclear atoms of 5 to 40 heteroaryl group, C ₅ ~ C ₄₀ aryloxy, C ₁ ~ C ₄₀ alkyl-oxy, C ₅ ~ C ₄₀ arylamino, C ₅ ~ C ₄₀ of diarylamino , (Aryl of C ₅ -C ₄₀ ) C ₁ -C ₄₀ alkyl, C ₃ -C ₄₀ cycloalkyl, and heterocycloalkyl having 3 to 40 nuclear atoms; Or a group capable of forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group.

The present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer One provides an organic electroluminescent device characterized in that it comprises a compound represented by the formula (1).

The compound represented by Chemical Formula 1 may be included in the emission layer.

In the present invention, by applying the compound represented by the formula (1) as a material for an organic light emitting device, preferably a phosphorescent light emitting layer material, energy transfer from the host to the dopant can be made smoother than when using a conventional light emitting material Therefore, various characteristics such as luminous efficiency, brightness, power efficiency, thermal stability, and device life of the organic EL device may be improved, and further, the performance and life of the full color organic EL panel may be maximized. .

Hereinafter, the present invention will be described in detail.

The compound represented by Chemical Formula 1 according to the present invention may be used as a phosphorescent light emitting layer material, specifically a phosphorescent host in an organic light emitting device, and has a functional group such as a triphenylene group having a high triplet energy in a molecule thereof. The energy band gap can be adjusted, and when the compound is used in the organic electroluminescent device, the energy can be smoothly transferred from the host to the dopant, thereby lowering the driving voltage. As a result, the organic electroluminescent device including the compound as a host capable of combining with a dopant not only improves driving voltage and lifespan, but also provides luminous efficiency, brightness, power efficiency, thermal stability, and the like. Properties can be improved.

In the compound represented by Formula 1, Ar ₁ to Ar ₄ are each independently halogen, amino, nitrile, nitro, C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C ₁ -C ₄₀ Substituted by one or more substituents selected from the group consisting of alkoxy, C ₃ to C ₄₀ cycloalkyl, heterocycloalkyl of 3 to 40 nuclear atoms, aryl of C ₆ to C ₄₀ and heteroaryl of 5 to 40 nuclear atoms Can be.

Preferably, at least one of Ar ₃ and Ar ₄ may be represented by a formula selected from the group consisting of the following Formulas 2 to 7.

(2)

;

;

(3)

;

;

[Formula 4]

;

;

[Chemical Formula 5]

;

;

[Formula 6]

; 및

; And

[Formula 7]

,

,

,

, 및

로 이루어진 군에서 선택되고,In Formulas 2 to 7, Q ₁ and Q ₂ are the same as or different from each other, and each independently hydrogen,

,

,

,

, And

, ≪ / RTI >

이며,E ₁ is hydrogen or

Is,

Z and Z ₁ are each independently C or Si.

And R ₁ to R ₄ are each independently C ₁ -C ₄₀ alkyl, C ₂ -C ₄₀ alkenyl, C ₁ -C ₄₀ alkoxy, C ₃ -C ₄₀ cycloalkyl, nuclear atom 3 It may be substituted with one or more substituents selected from the group consisting of heterocycloalkyl of 40 to 40, aryl of C ₆ ~ C ₄₀ and heteroaryl of 5 to 40 nuclear atoms.

Examples of the compound represented by Formula 1 according to the present invention include a compound represented by the following Formula 1a, but is not limited thereto.

[Formula 1a]

In Formula 1a, Ar ₃ , Ar _4, X, and Y are the same as defined in Formula 1 above.

Preferably, at least one of Ar ₃ and Ar ₄ of Formula 1a may be represented by a formula selected from the group consisting of Formulas 2 to 7.

Specific examples of the compound represented by Formula 1 include the following compounds In-1 to In-24, but are not limited thereto.

As used herein, "aromatic ring" means an aromatic moiety having 6 to 40 carbon atoms, singly or in combination of two or more rings. Two or more rings may be attached to each other in a pendant or fused form to each other. Examples thereof include aryl, heteroaryl, aryloxy, arylamino, diarylamino, arylalkyl, and the like, specifically, phenyl, biphenyl, naphthyl, anthracenyl, and dianthracenyl. Phenylaminophenyl, diphenylaminophenyl, phenanthryl, pyrenyl, or terphenyl, but are not limited thereto.

"Alkyl" is a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples of which include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

"Alkenyl" means a radical comprising one or more carbon-carbon double bonds at the center or terminus of alkyl having 2 to 40 carbon atoms. Examples of alkenyl include, but are not limited to, ethylene, propylene, butylene, hexylene, and the like.

"Alkynyl" means a radical comprising at least one carbon-carbon triple bond at the center or terminus of an alkyl having from 2 to 40 carbon atoms.

"Aryl" means an aromatic moiety having 5 to 40 carbon atoms, either singly or in combination of two or more rings, and is referred to herein as "aryloxy", "arylalkyl" and the like. Two or more rings may be attached to each other in a pendant or fused form to each other. Examples of aryl include, but are not limited to, phenyl, biphenyl, naphthyl, anthracene, anthryl, phenanthryl, and the like.

"Heteroaryl" means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 40 nuclear atoms, wherein at least one carbon, preferably 1 to 3 carbons in the ring is hetero, such as N, O or S Replaced by an atom. Two or more rings may be attached to each other in a pendant or fused form to each other. It is further construed to include condensed forms with aryl groups. Examples of heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Polycycles such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl A ring, and is interpreted to include, but is not limited to, 2-funnaryl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.

"Aryloxy" includes, but is not limited to, phenyloxy, naphthyloxy, diphenyloxy and the like having 5 to 40 carbon atoms.

"Alkoxyoxy" is oxy substituted by alkyl having 1 to 40 carbon atoms, "arylamino" is amino substituted by aryl having 5 to 40 carbon atoms, and "diarylamino" is aryl having 5 to 40 carbon atoms.

"Arylalkyl" is also called aralkyl, and examples thereof include, but are not limited to, benzyl, phenylethyl and the like.

"Cycloalkyl" includes monocyclic or polycyclic nonaromatic hydrocarbon groups having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and the like.

"Heterocycloalkyl" means a non-aromatic moiety of 3 to 40 nuclear atoms, in which one or more carbons in the ring, preferably 1 to 3 carbons, are replaced with a hetero atom such as N, O or S. Non-limiting examples thereof include morpholine, piperazine, and the like.

"Alkoxy" means alkyl with 1 to 40 carbon atoms attached to oxygen and is interpreted to include a straight, branched or cyclic structure. Examples of alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

The compound represented by Chemical Formula 1 of the present invention may be synthesized according to a general method for synthesizing a compound. Detailed synthesis of the compound of the present invention will be described in detail in Synthesis Examples to be described later.

On the other hand, the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).

Specifically, the present invention is an organic electroluminescent device comprising (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 one or more organic material layers is characterized in that it comprises a compound represented by the formula (1).

The organic material layer including the compound represented by Chemical Formula 1 is preferably an emission layer. When the compound represented by Chemical Formula 1 is used as a phosphorescent host material capable of bonding with a material of the light emitting layer, for example, a phosphorescent dopant, energy may be smoothly transferred from the host to the dopant. The EL device may improve luminous efficiency, brightness, power efficiency, thermal stability, and device life.

On the other hand, in the organic electroluminescent device according to the present invention, the organic material layer other than the organic material layer containing the compound represented by the formula (1) of the present invention may be a hole injection layer, a hole transport layer, an electron injection layer and / or an electron transport layer.

As a non-limiting example of the organic electroluminescent device structure according to the present invention, a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked. In this case, the light emitting layer includes a compound represented by Chemical Formula 1. An electron injection layer may be disposed on the electron transport layer. In addition, a hole blocking layer may be positioned between the light emitting layer and the electron hydrogen layer.

In addition, as described above, the organic electroluminescent device according to the present invention may not only have a structure in which an anode, at least one organic material layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.

In the organic electroluminescent device according to the present invention, the organic material layer including the compound represented by Chemical Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

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

For example, a silicon wafer, quartz or glass plate, a metal plate, a plastic film or a sheet can be used as the substrate.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

Further, the hole injection layer material, the hole transport layer material and the electron transport layer material, and optionally the electron injection layer material and / or the hole blocking layer material are not particularly limited, and conventional materials known in the art may be used.

Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

≪ Example 1 >

Example 1-1 Synthesis of Compound In-1

(Synthesis step 1-1) Synthesis of Intermediate 4,5-diphenylcyclohexa-3,5-diene-1,2-dione

[Reaction Scheme 1-1]

40 g (1 eq, 0.15 mol) of compound 1 (4,5-dibromocyclohexa-3,5-diene-1,2-dione) of scheme 1-1, phenylboronic acid 22.01 g (2.2 eq, 0.36 mol), and tetrakis 5.19 g (0.03 eq, 0.0045 mol) of (triphenylphosphine) palladium (0) [Pd (PPh ₃ ) _{4 was} added to 100 ml of 2M saturated aqueous K ₂ CO ₃ solution and 500 ml of toluene and dissolved, followed by heating and stirring for 12 hours. .

After the reaction was completed, the reaction solution was filtered through Celite, extracted with dichloromethane, and recrystallized with hexane to give an intermediate compound 2 (4,5-diphenylcyclohexa-3,5-diene-1,2- dione) 34.6 g (yield: 88.7%).

GC-Mass (Theoretical value: 455.30 g / mol, Measured value: 454 g / mol)

(Synthesis step 1-2) Synthesis of Intermediate triphenylene-2,3-dione

[Reaction Scheme 1-2]

24 g (1 eq, 0.13 mol) of Compound 2 (4,5-diphenylcyclohexa-3,5-diene-1,2-dione) obtained in the synthesis step 1-1 was added to 42.3 g (2 eq. 0.261 mol) of FeCl ₃ . After mixing with them, they were added to 500 ml of dichloromethane. Thereafter, the reaction solution was stirred at room temperature for 24 hours.

After the reaction was completed, the reaction product was washed with distilled water, extracted, filtered with a Silica filter to remove the solvent, and then purified by column chromatography to give the intermediate compound 2 (triphenylene-2,3-dione) 26.1 g (yield) : 78%).

¹ H-NMR: 8.29 (d, 2H), 7.37 (m, 4H), 7.17 (t, 2H), 6.45 (s, 2H),

HRMS for [M] +: 257

(Synthesis Step 1-3) Synthesis of Intermediate 12-bromo-10,15-dihydrophenanthro [9,10-b] phenazine

[Reaction 1 - 3]

25 g (1 eq, 0.096 mol) of compound 3 (triphenylene-2,3-dione) obtained in Synthesis Step 1-2 and 19.9 g (1.1 eq, 0.106 mol) of 4-bromobenzene-1,2-diamine were mixed. Thereafter, these were added to 300 ml of acetic acid to dissolve and stirred under reflux for 12 hours. Subsequently, the solid obtained by adding the reaction solution to distilled water was filtered and washed several times with distilled water, and then the filtered solid was purified by column chromatography to obtain Compound 4 (12-bromo-10,15-dihydrophenanthro [9,]) as an intermediate. 10-b] phenazine) 26.8 g (yield: 64%).

HRMS for [M] +: 410

Synthesis of Intermediate 12-bromo-10,15-diphenyl-10,15-dihydrophenanthro [9,10-b] phenazine

Scheme 1-4

25 g (1 eq, 0.06 mol) of compound 4 (12-bromo-10,15-dihydrophenanthro [9,10-b] phenazine) obtained in the synthesis steps 1-3, 27.2 g (2.2 eq, 0.133 mol) of iodobenzene and 2.07 g (0.03 eq, 1.8 mmol) of Pd (PPh ₃ ) ₄ were mixed and then dissolved in 70 ml of 2M saturated aqueous K ₂ CO ₃ solution and 300 ml of toluene, followed by heating and stirring for 12 hours.

After the reaction was completed, the reaction solution was filtered through Celite, extracted with dichloromethane and purified by column chromatography to give the intermediate compound 5 (12-bromo-10,15-diphenyl-10,15-dihydrophenanthro [ 9,10-b] phenazine) 24.3 g (yield: 72%).

HRMS for [M] +: 562

(Synthesis Step 1-5)-Synthesis of Compound In-1

Scheme 1-5

10 g (1 eq, 0.017 mol) of compound 5 (12-bromo-10,15-diphenyl-10,15-dihydrophenanthro [9,10-b] phenazine) obtained in the synthesis steps 1-4, dibenzo [b, d ] 65.4 g (1.2 eq, 0.02 mol) of] thiophen-4-ylboronic acid, and 0.65 g (0.03 eq, 5.7 mmol) of Pd (PPh ₃ ) ₄ were mixed, and then 50 ml of a saturated aqueous solution of 2M K ₂ CO ₃ and The solution was dissolved in 250 ml of toluene and heated and stirred for 12 hours.

After the reaction was completed, the reaction solution was filtered through Celite, extracted with dichloromethane, and the resulting compound 1-1 g (yield: 88.7%) by column chromatography.

Elemental Analysis for: C, 86.20; H, 4. 82; N, 4.19; S, 4.79

HRMS for [M] ⁺ : 667

Example 1-2 Fabrication of Organic Electroluminescent Device

An organic electroluminescent device was fabricated in the following manner.

A glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1500 kPa was washed by distilled water ultrasonically. After the washing of distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried and transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using oxygen plasma, and then the substrate was transferred to a vacuum depositor.

After the vacuum injection of DS-205 (Doosan Co., Ltd.) to a thickness of 800 kPa on the prepared ITO transparent electrode (anode) as described above to form a hole injection layer, a-NPB ( N , N- di on the hole injection layer (naphthalene-1-yl) -N , N- diphenylbenzidine) was vacuum deposited to a thickness of 150 kPa to form a hole transport layer, and the compounds In-1 and Ir (ppy) ₃ synthesized in Example 1-1 were added thereto. Was vacuum deposited to a thickness of 300 kPa to form a light emitting layer.

Subsequently, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) was formed on the emission layer to form a hole blocking layer having a thickness of 200 kPa, and Alq3 was then vacuum deposited to a thickness of 250 kPa. A transport layer was formed.

Subsequently, an electron injection layer is formed by depositing LiF to a thickness of 10 kW on the electron hydrogen layer, and then an aluminum (Al) is vacuum deposited to a thickness of 2000 kW on the electron injection layer to form a cathode. Was prepared.

<Example 2>

Example 2-1 Synthesis of Compound In-3

Use of 2- (dibenzo [b, d] thiophen-4-yl) phenylboronic acid instead of dibenzo [b, d] thiophen-4-ylboronic acid used in Synthesis Step 1-5 of Example 1-1 Except, in the same manner as in Synthesis Step 1-5 of Example 1-1, to obtain 17.4 g (yield: 89.9%) of the compound In-3 as a white solid.

Elemental Analysis for: C, 87.06; H, 4.87; N, 3.76; S, 4.30

HRMS for [M] ⁺ : 743

Example 2-2 Fabrication of Organic Electroluminescent Device

In the same manner as in Example 1-2 except for using the compound In-3 synthesized in Example 2-1 instead of the compound In-1 used as the emission layer material in Example 1-2, An electroluminescent device was manufactured.

<Example 3>

Example 3-1 Synthesis of Compound In-6

9H-carbazole was substituted for dibenzo [b, d] thiophen-4-ylboronic acid used in Synthesis Step 1-5 of Example 1-1. Aside from using, the same procedure as in Synthesis Step 1-5 of Example 1-1 to give 11.9 g (yield: 82.1%) of a compound In-6 as a white solid.

Elemental Analysis for: C, 88.45; H, 5. 10; N, 6.45

HRMS for [M] ⁺ : 650

Example 2-2 Fabrication of Organic Electroluminescent Device

Except for using the compound In-6 synthesized in Example 3-1 instead of the compound In-1 used as a light emitting layer material in Example 1-2, it was carried out in the same manner as in Example 1-2 An electroluminescent device was manufactured.

<Example 4>

Example 4-1 Synthesis of Compound In-7

Using 3- (dibenzo [b, d] thiophen-2-yl) phenylboronic acid instead of dibenzo [b, d] thiophen-4-ylboronic acid used in Synthesis Step 1-5 of Example 1-1 Except that in the same manner as in Synthesis Step 1-5 of Example 1-1, 13.1 g (yield: 79%) of a compound In-7 was obtained as a white solid.

Elemental Analysis for: C, 87.06; H, 4.87; N, 3.76; S, 4.30

HRMS for [M] ⁺ : 743

Example 4-2 Fabrication of Organic Electroluminescent Device

Except for using the compound In-7 synthesized in Example 4-1 instead of the compound In-1 used as the emission layer material in Example 1-2, it was carried out in the same manner as in Example 1-2 An electroluminescent device was manufactured.

<Example 5>

Example 5-1 Synthesis of Compound In-8

Except for using 6,9-diphenyl-9H-carbazol-3-ylboronic acid in place of dibenzo [b, d] thiophen-4-ylboronic acid used in Synthesis Step 1-5 of Example 1-1 In the same manner as in Synthesis Step 1-5 of Example 1-1, 10.3 g of a compound In-8 (a yield: 83.4%) was obtained.

Elemental Analysis for: C, 89.63; H, 5. 14; N, 5.23

HRMS for [M] ⁺ : 802

Example 5-2 Fabrication of Organic Electroluminescent Device

In the same manner as in Example 1-2 except for using the compound In-8 synthesized in Example 5-1 instead of the compound In-1 used as the emission layer material in Example 1-2, An electroluminescent device was manufactured.

<Example 6>

Example 6-1 Synthesis of Compound In-9

Example 1-1 except that 3,6-diphenyl-9H-carbazole was used instead of the dibenzo [b, d] thiophen-4-ylboronic acid used in Synthesis Step 1-5 of Example 1-1. Synthesis of -1 was carried out in the same manner as in Step 1-5, to obtain 14.2 g (yield: 86.4%) of the compound In-9 as a white solid.

Elemental Analysis for: C, 89.63; H, 5. 14; N, 5.23

HRMS for [M] ⁺ : 802

Example 6-2 Fabrication of Organic Electroluminescent Device

In the same manner as in Example 1-2 except for using the compound In-9 synthesized in Example 6-1 instead of the compound In-1 used as the emission layer material in Example 1-2, An electroluminescent device was manufactured.

&Lt; Example 7 >

Example 7-1 Synthesis of Compound In-11

Except for using 2- (9H-carbazol-9-yl) phenylboronic acid instead of dibenzo [b, d] thiophen-4-ylboronic acid used in Synthesis Step 1-5 of Example 1-1, 13.2 g (yield: 85.9%) of the compound In-11 as a white solid was obtained in the same manner as in Synthesis Step 1-5 of Example 1-1.

Elemental Analysis for C: 89.10; H, 5. 12; N, 5.77

HRMS for [M] ⁺ : 726

Example 7-2 Fabrication of Organic Electroluminescent Device

In the same manner as in Example 1-2 except for using the compound In-11 synthesized in Example 7-1 instead of the compound In-1 used as the emission layer material in Example 1-2, An electroluminescent device was manufactured.

&Lt; Example 8 >

Example 8-1 Synthesis of Compound In-13

Synthesis step of Example 1-1 except for using (chloromethanetriyl) tribenzene instead of dibenzo [b, d] thiophen-4-ylboronic acid used in Synthesis Step 1-5 of Example 1-1 9.6 g (yield: 76.7%) of the compound In-13 was obtained as a white solid.

Elemental Analysis for C: 90.63; H, 5.53; N, 3.84

HRMS for [M] ⁺ : 727.

Example 8-2 Fabrication of Organic Electroluminescent Device

Except for using the compound In-13 synthesized in Example 8-1 instead of the compound In-1 used as a light emitting layer material in Example 1-2, it was carried out in the same manner as in Example 1-2 An electroluminescent device was manufactured.

&Lt; Example 9 >

Example 9-1 Synthesis of Compound In-16

3 '-(9-phenyl-9H-carbazol-3-yl) biphenyl-3-ylboronic instead of dibenzo [b, d] thiophen-4-ylboronic acid used in Synthesis Step 1-5 of Example 1-1 Except for using acid, in the same manner as in Synthesis Step 1-5 of Example 1-1 to obtain 13.8 g of a white solid compound In-16 (yield: 72.6%).

Elemental Analysis for C: 90.07; H, 5.15; N, 4.77

HRMS for [M] ⁺ : 879

Example 9-2 Fabrication of Organic Electroluminescent Device

In the same manner as in Example 1-2 except for using the compound In-16 synthesized in Example 9-1 instead of the compound In-1 used as the emission layer material in Example 1-2, An electroluminescent device was manufactured.

< Comparative Example  1> organic Field  Manufacturing of light emitting device

CBP (4,4-dicarbazolybiphenyl, or 4,4'-di (9H-carbazol-9), which is a host material that is frequently used in green phosphorescent devices, instead of the compound In-1 used to form the light emitting layer in Example 1-2 An organic electroluminescent device was manufactured in the same manner as in Example 1, except that -yl) biphenyl) was used.

< Experimental Example  1> organic Field  Driving voltage and luminous efficiency of light emitting device

For the organic electroluminescent devices manufactured in Examples 1 to 9 and Comparative Example 1, the luminous efficiency was measured at a current density of 10 mA / cm 2, and the results are shown in Table 1 below.

Host material The driving voltage (V) Luminous Efficiency (cd / A) Example 1 Compound In-1 6.01 60.2 Example 2 Compound In-3 5.99 59.8 Example 3 Compound In-6 6.2 66.9 Example 4 Compound In-7 5.7 72.9 Example 5 Compound In-8 5.73 54.2 Example 6 Compound In-9 5.61 55.4 Example 7 Compound In-11 5.9 63.7 Example 8 Compound In-13 5.95 73.2 Example 9 Compound In-16 6.04 60.1 Comparative Example 1 CBP 6.22 44.79

As a result of the experiment, the organic electroluminescent devices of Examples 1 to 9 using the compound according to the present invention showed lower driving voltage and higher luminous efficiency than the organic electroluminescent device of Comparative Example 1 using the conventional CBP. From this, it was confirmed that the compound according to the present invention can be used as a material of the organic electroluminescent device, thereby improving driving voltage and luminous efficiency of the device.

< Experimental Example  2> organic Field  Life characteristics of light emitting device

For the organic electroluminescent devices manufactured in Examples 1 to 9 and Comparative Example 1, respectively, the time taken to decrease to the luminance corresponding to 97% of the luminance at the start of driving was set to 9000 nit as the driving time of the element elapsed. The average values are shown in Table 2 below.

Host material T = 97% / hr Example 1 Compound In-1 104 Example 2 Compound In-3 99 Example 3 Compound In-6 107 Example 4 Compound In-7 150 Example 5 Compound In-8 96 Example 6 Compound In-9 89 Example 7 Compound In-11 109 Example 8 Compound In-13 120 Example 9 Compound In-16 115 Comparative Example 1 CBP 78

As a result of the test, the organic electroluminescent devices of Examples 1 to 9 using the compound according to the present invention showed better life characteristics than the organic electroluminescent device of Comparative Example 1 using the conventional CBP.

Although preferred embodiments 1 to 9 of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention. Naturally, it belongs to the range of.

Claims (7)

Compound represented by the following formula (1a):
[Formula 1a]

(In the formula (1a)
Ar ₃ and Ar ₄ are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, and C ₆ -C ₄₀ aromatic rings, or are bonded to adjacent groups to form a fused aliphatic ring, condensation Can form an aromatic ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring,
At this time, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently halogen, amino, nitrile, nitro, C ₁ ~ C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl, C ₁ ~ C ₄₀ alkoxy , C ₃ -C ₄₀ cycloalkyl, and heterocycloalkyl of 3 to 40 nuclear atoms, aryl of C ₆ ~ C ₄₀ and heteroaryl of 5 to 40 nuclear atoms to be substituted with one or more substituents Can,
X and Y are each independently selected from the group consisting of NA ¹ , S and O,
A ¹ is hydrogen, deuterium, C ₁ ~ C ₄₀ alkyl, C ₂ ~ C ₄₀ alkenyl, C ₂ ~ C ₄₀ alkynyl, C ₅ ~ C ₄₀ aryl, nuclear 5 to 40 hetero Aryl, C ₅ -C ₄₀ aryloxy, C ₁ -C ₄₀ alkyloxy, C ₅ -C ₄₀ arylamino, C ₅ -C ₄₀ diarylamino, (C ₅ -C ₄₀ aryl) C ₁ -C ₄₀ alkyl, C ₃ -C ₄₀ cycloalkyl and heterocycloalkyl having 3 to 40 nuclear atoms. delete delete delete The method of claim 1,
At least one of Ar ₃ and Ar ₄ is a compound characterized in that represented by the formula selected from the group consisting of Formulas 2 to 5, and 7.
(2)

;
(3)

;
[Chemical Formula 4]

;
[Chemical Formula 5]

; And
(7)

(In the formulas 2 to 5, 7, Q ₁ and Q ₂ are the same as or different from each other, and each independently hydrogen,

,

,

,

, And

, &Lt; / RTI &gt;

E ₁ is hydrogen or

Is,
Z ₁ is C or Si). 1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched between the anode and the cathode,
At least one of the at least one organic layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1a) according to claim 1 or 5. The organic electroluminescent device according to claim 6, wherein the organic material layer including the compound represented by Chemical Formula 1a is a light emitting layer.