KR20190028878A - Arylamine derivative and organic electro luminescent device including the same - Google Patents

Abstract

Provided is an arylamine derivative represented by chemical formula 1. In the chemical formula 1, a definition of each substituent is as defined in a description of the invention. The present invention provides an organic electroluminescent device having a low driving voltage and improved light emitting efficiency by incorporating the arylamine derivative into an organic material layer constituting the organic electroluminescent device.

Description

[0001] The present invention relates to an arylamine derivative including a carbazole and a carbene, and an organic electroluminescent device including the arylamine derivative and an organic electroluminescent device including the same.

The present invention relates to an arylamine derivative and an organic electroluminescent device including the same. More particularly, the present invention relates to an organic electroluminescent device having high luminous efficiency and a novel arylamine derivative for the same.

In 1987, Tang and Van Slyke reported the characteristics of high efficiency using a multilayer thin film structure of an organic light emitting diode (OLED) [Tang, C. W., Van Slyke, S. A. Appl. Phys. Lett. 51, 91 (1987)], OLEDs have a great potential to be used for LCD backlighting and illumination as well as excellent characteristics as a next generation display [Kido, J., Kimura, M., and Nagai, K. , Science 267,1332 (1995)].

Especially, in order to increase the luminous efficiency, various approaches such as structural change and material development have been performed [Sun, S., Forrest, S. R., Appl. Phys. Lett. 91, 263503 (2007) / Ken-Tsung Wong, Org. Lett., 7, 2005, 5361-5364].

By optimizing the hole transport layer, proper exciton distribution and energy transfer in the light emitting layer are controlled, so that it is important to study a device that emits light with a balanced color.

The optimization of the hole transport layer is to stably supply the holes introduced through the hole injection layer to the light emitting layer.

This is because if the HOMO level of the hole transport layer is higher than the HOMO level of the light emitting layer, the hole transport becomes smooth. In this case, the hole mobility of the hole transporting layer is influenced by the charge balancing effect (the effect of achieving high efficiency light efficiency only when the number of holes and electrons is similar to that of the light emitting layer) It is an important factor of performance improvement.

The hole transport materials of the hole transport layer generally include an electron donor component, which can be considered as a p-type semiconductor, and is mainly composed of an aromatic amine.

As a typical example of the material of the hole transport layer, there are arylamine type NPB and fluorene type TPD, and carbazole type derivatives have also been studied variously as a hole transport layer material .

The hole transport material not only transports holes easily but also binds electrons to the light emitting region, thereby increasing the probability of forming an exciton. For this, a property of high hole mobility and a glass transition temperature (Tg) of 120 ° C or more is required.

This is because, in the organic light emitting device, joule heating occurs due to the movement of charges. Therefore, the material used in the organic light emitting device is preferably excellent in thermal stability.

NPB, which is mainly used as a hole transporting material in a hole transporting layer, has a glass transition temperature of 100 ° C or less, which is difficult to use in an organic light emitting device requiring a high current. TPD was initially used as a hole transport material, but the glass transition temperature (Tg) was unstable at about 60 ° C. and the spiro-TAD, which is a NPD or TPD fluorene dimer, (HTL).

 In addition, it is preferable that the material used in the organic light emitting device is less deformed by moisture or oxygen. In addition, it is preferable that the density of holes and electrons is balanced in the light emitting layer of the organic light emitting device by having a suitable hole or electron mobility to maximize the formation of excitons. In addition, for the stability of the device, it is necessary to improve the interface with the electrode containing metal or metal oxide.

Therefore, research on such organic EL materials is continuously required.

Korean Patent Publication No. 10-1292554 (title of the invention: compound, organic electric device using the same and electronic device thereof) Korean Patent Registration No. 10-1653539 (entitled "Organic Electroluminescent Device")

The object of the present invention is to provide a novel arylamine derivative which is superior in luminous efficiency and durability to a conventional material for an organic electroluminescent device and is characterized in that the arylamine derivative is added to an organic material layer constituting an organic electroluminescent device And to provide an organic electroluminescent device having a low driving voltage and improved luminous efficiency.

According to an aspect of the present invention, there is provided an arylamine derivative represented by the following general formula (1).

[Chemical Formula 1]

[In the formula 1,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are each independently hydrogen, substituted or unsubstituted C ₁ -C ₃₀ alkyl, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl, Substituted or unsubstituted C ₆ -C ₃₀ aryl, substituted or unsubstituted C ₆ -C ₃₀ aralkyl, substituted or unsubstituted C ₁ -C ₃₀ heteroalkyl, substituted or unsubstituted C ₂ -C ₃₀ hetero Cycloalkyl, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl, substituted or unsubstituted C ₅ -C ₃₀ heteroaralkyl,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ adjacent to each other in one ring are each a substituted or unsubstituted C ₃ -C ₂₀ alkylene or a substituted or unsubstituted C ₃ -C ₂₀ alkenylene They may be connected to each other to form a fused ring,

p, q, r, s, t and u are integers of 1 to 4,

X ₁ , X ₂ and X ₃ are each independently selected from CH or N, and at least one of them is N.

According to another aspect of the present invention, there is provided an organic electroluminescent device comprising the arylamine derivative described above.

According to another aspect of the present invention, there is provided an organic electroluminescent device including a first electrode, a second electrode, and one or more organic layers disposed between the electrodes, Is provided.

The arylamine derivative according to an embodiment of the present invention may be included in an organic layer of an organic electroluminescent device, preferably a hole injection layer or a hole transport layer, thereby lowering the driving voltage of the device and improving the luminous efficiency. In particular, the thermal stability of the compound can improve the lifetime of the device.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.
2 shows NMR analysis results of Compound 3-1 (DC1A-md-C3) of the present invention.
3 shows NMR analysis results of Compound 3-2 (C1A-md-DC3) of the present invention.
4 shows NMR analysis results of the compound 3-3 (C3A-md-DC3) of the present invention.
5 is a photoluminescence (PL) spectrum measured at a low temperature (77 K) using a Jasco FP-8500 instrument for the OLED compound of the present invention.
6 is a graph showing PL (PL) values measured at low temperature (77K) using a Jasco FP-8500 instrument against CBP (4,4'-di (9H-carbazol- (photoluminescence) spectrum.

Hereinafter, the present invention will be described in detail.

The arylamine derivative according to an embodiment of the present invention may be represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are each independently hydrogen, substituted or unsubstituted C ₁ -C ₃₀ alkyl, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl, Substituted or unsubstituted C ₆ -C ₃₀ aryl, substituted or unsubstituted C ₆ -C ₃₀ aralkyl, substituted or unsubstituted C ₁ -C ₃₀ heteroalkyl, substituted or unsubstituted C ₂ -C ₃₀ hetero Cycloalkyl, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl, substituted or unsubstituted C ₅ -C ₃₀ heteroaralkyl

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ each independently represent an alkyl group having 1 to 4 carbon atoms in one ring Quot; means the same or different types. For example, in the case of (R ₁ ) ₄ , it can be seen that four rings of the same or different R ₁ are substituted in one ring.

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ adjacent to each other in each ring may be substituted or unsubstituted C ₃ -C ₂₀ alkylene or substituted or unsubstituted C ₃ -C ₂₀ < / RTI > alkenylene to form a fused ring.

X ₁ , X ₂ and X ₃ are each independently selected from CH or N, and at least one of them is N.

The compound represented by Formula 1 may be selected from among the structures represented by Formula 2 below.

(2)

In Formula 2, R ₁ , R ₂ , R ₄ , R ₅ and R ₆ are as defined in Formula 1.

More specifically, the carbazole and carbazole-substituted arylamine derivatives represented by Formula 1 may be selected from one of the compounds represented by Formula 3 below, but the present invention is not limited thereto.

(3)

The carbazole and carbene-substituted arylamine derivatives represented by Formula 1 can be synthesized using a known organic synthesis method. The method of synthesizing the arylamine derivative can be easily recognized by those skilled in the art with reference to the following Production Examples.

Also, according to the present invention, there is provided an organic electroluminescent device comprising carbazole and carbene-substituted arylamine derivative represented by the above formula (1).

The carbazole and carbene-substituted arylamine derivatives of Formula 1 are useful as a hole injection layer material or a hole transport layer material, and may be used as a host material for fluorescent and phosphorescent devices that emit blue, green, and red colors .

The organic electroluminescent device according to the present invention includes a first electrode, a second electrode, and one or more organic layers disposed between the electrodes. The organic material layer contains at least one carbazole and an allylamine derivative substituted with carbolin represented by the general formula (1).

The organic material layer may include a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a buffer layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, And at least one layer selected from the group consisting of functional layers having at the same time.

For example, the arylamine derivative may be included in at least one selected from the group consisting of a light emitting layer, an organic material layer disposed between the anode and the light emitting layer, and an organic material layer disposed between the light emitting layer and the cathode. Preferably, the arylamine derivative may be contained in one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, and a functional layer having both a hole injection function and a hole transport function. The arylamine derivative may be included in the organic material layer as a single material or a combination of different materials. The arylamine derivative may be used in combination with a compound known in the art such as a hole transport layer and a hole injection layer.

The organic electroluminescent device according to the present invention can be applied to an organic electroluminescent device including a positive electrode / a light emitting layer / a cathode, a positive electrode / a hole injecting layer / a light emitting layer / a negative electrode, an anode / a hole injecting layer / a hole transporting layer / a light emitting layer / an electron transporting layer / / Light emitting layer / electron transporting layer / electron injecting layer / cathode structure.

Alternatively, the organic electroluminescent device may include a functional layer / a light emitting layer / an electron transporting layer / a cathode having both an anode / hole injecting function and a hole transporting function, a functional layer / a light emitting layer / an electron transporting layer / Electron injecting layer / cathode structure, but the present invention is not limited thereto.

1 is a schematic cross-sectional view of an organic electroluminescent device according to an embodiment of the present invention.

The organic electroluminescent device may be manufactured using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.

For example, an anode is formed by depositing a metal or metal oxide having conductivity or an alloy thereof on a substrate, and an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer is formed thereon And then depositing a material which can be used as a cathode thereon.

In addition to such a method, an organic electroluminescent device may be fabricated by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may be prepared by a solution process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, instead of using a vapor deposition method using various polymer materials .

The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

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

Example  1: Compound 3-1 ( DC1A -md-C3)

The synthesis route of DC1A-md-C3 is shown below.

(Synthesis of Intermediate 1)

In a two-neck 250 ml flask, 7 g (42 mmol) of 隆 -carboline, 9.3 g (46 mmol) of 1-bromo-3-nitrobenzene, 0.52 g (3 mmol) 0.94 g (5 mmol) of 1,10-phenanthroline, 22 g (104 mmol) of K ₃ PO ₄ and 120 ml of dioxane were added thereto and refluxed in a nitrogen atmosphere at 80 to 100 ° C for 24 hours. After the reaction was completed, the reaction product was dissolved in methylene chloride (MC) and filtered using Celite. The filtered solution was distilled under reduced pressure and extracted with MC and distilled water. The extracted MC layer was dehydrated with MgSO ₄ , and the solvent was removed by distillation under reduced pressure to obtain a yellow solid. The solid was separated from the white solid ( 1 ) (7.5 g, yield: 65%) by column chromatography.

(Synthesis of intermediate 2)

10 g (35 mmol) of Intermediate 1 and 100 ml of 2N acetic acid were placed in a two-necked 250 ml flask and stirred. After 30 minutes, 11.6 g (208 mmol) of Fe was added and stirred vigorously at room temperature for 5 to 6 hours. After the reaction was completed, the reaction was dissolved in MC and filtered using Celite. The filtered solution was distilled under reduced pressure and then extracted with MC and Na ₂ CO ₃ (sat) or Na ₂ CO ₃ (sat) + NaCl (sat). The extracted MC layer was dehydrated with MgSO ₄ , and the solvent was removed by distillation under reduced pressure to obtain a yellow solid. The solid was separated into a white solid (2) (6.5 g, yield: 71%) by column chromatography.

(Synthesis of Compound 3-1)

In a two-necked 250 ml flask Intermediate 2 0.6g (2.3mmol), 9- ( 3- bromo-phenyl) -9H- carbazole (9- (3-bromophenyl) -9H -carbazole) 1.7g (5mmol), NaO t Bu 0.67g (6.9mmol ) Were placed in 100 ml of toluene, stirred in a nitrogen atmosphere, and the reaction temperature was raised to 80 ° C and reacted for 1 hour. 0.07 g (0.07 mmol) of Pd ₂ (dba) _{3 and} 0.02 g (0.09 mmol) of (tert-Bu) ₃ P were added thereto and reacted at 80 ° C. for 4 to 5 hours. The reaction solution was filtered to remove the salt. The filtrate was distilled to remove toluene and the concentrate was separated into a column, and the yield of Compound 3-1 (DC1A-md-C3) obtained was 1.0 g (yield: 62%). NMR analysis results of Compound 3-1 (DC1A-md-C3) obtained are as follows (see Fig. 2 below).

NMR ^{analysis: 1 H NMR (300MHz, DMSO} ) δ 8.56 (d, 1H), 8.30 (d, 1H), 8.23 (m, 4H), 7.88 (m, 1H), 7.66 (m, 6H), 7.55 ( m, 8H), 7.45 (m, 8H), 7.37 (m,

Example  2: Compound 3-2 ( C1A -md-DC3)

The synthesis route of C1A-md-DC3 is shown below.

(Synthesis of Intermediate 3)

In a two-neck 250 ml flask, 15 g (89 mmol) of 隆 -carboline, 37.8 g (134 mmol) of 1-bromo-3-iodobenzene, 1.1 g (5.79 mmol) 2 g (11.13 mmol) of phenanthroline, 47 g (220 mmol) of K ₃ PO ₄ and 300 ml of dioxane were added thereto and refluxed in a nitrogen atmosphere at 80 to 100 ° C for 24 hours. After the reaction was completed, the reaction was dissolved in MC and filtered using Celite. The filtered solution was distilled under reduced pressure and extracted with methylene chloride and distilled water. The extracted Methylene Chloride layer was dehydrated with MgSO ₄ , and the solvent was removed by distillation under reduced pressure to obtain a yellow solid. The white solid (3) was isolated (18.0 g, yield: 62%) by Column Chromatography method.

(Synthesis of Compound 3-2)

0.6 g (2.3 mmol) of 3- (9H-carbazol-9-yl) aniline and 3 g (2.3 mmol) of Intermediate 3 1.7 g (5 mmol) of NaO ^t Bu and 0.67 g (6.9 mmol) of NaO ^t Bu were placed in 100 ml of toluene, and the mixture was stirred in a nitrogen atmosphere. The reaction temperature was raised to 80 ° C and reacted for 1 hour. 0.07 g (0.07 mmol) of Pd ₂ (dba) _{3 and} 0.02 g (0.09 mmol) of (tert-Bu) ₃ P were added thereto and reacted at 80 ° C. for 4 to 5 hours. The reaction solution was filtered to remove the salt. The filtrate was distilled to remove toluene and the concentrate was separated into a column, and the yield of Compound 3-2 (C1A-md-DC3) obtained was 1.0 g (yield: 66%). The NMR analysis results of the obtained compound 3-2 (C1A-md-DC3) are as follows (see FIG. 3).

NMR ^{analysis: 1 H NMR (300MHz, DMSO} ) δ 8.56 (m, 2H), 8.25 (m, 4H), 7.87 (m, 2H), 7.67 (m, 6H), 7.55 (m, 10H), 7.45 ( m, 6H), 7.37 (m, 2H), 7.28 (m, 2H)

Example  3: Compound 3-3 ( C3A -md-DC3)

The synthesis route of C3A-md-DC3 is shown below.

In a two-necked 250 ml flask Intermediate 2 0.6 g (2.3 mmol), intermediate 3 1.7 g (5 mmol) of NaO ^t Bu and 0.67 g (6.9 mmol) of NaO ^t Bu were placed in 100 ml of toluene, and the mixture was stirred in a nitrogen atmosphere. The reaction temperature was raised to 80 ° C and reacted for 1 hour. 0.07 g (0.07 mmol) of Pd ₂ (dba) _{3 and} 0.02 g (0.09 mmol) of (tert-Bu) ₃ P were added thereto and reacted at 80 ° C. for 4 to 5 hours. The reaction solution was filtered to remove the salt. The filtrate was distilled to remove toluene and the concentrate was separated into a column to obtain 1.1 g (yield: 68%) of the obtained compound 3-3 (C3A-md-DC3). The NMR analysis results of the obtained compound 3-3 (C3A-md-DC3) are as follows (see FIG. 4).

NMR ^{analysis: 1 H NMR (300MHz, DMSO} ) δ 8.54 (m, 3H), 8.28 (d, 3H), 7.75 (m, 3H), 7.65 (m, 12H), 7.54 (m, 3H), 7.44 ( m, 6 H), 7.36 (m, 3 H)

Test Example

The UV / VIS spectrum of the compound of the present invention was measured using a Jasco V-630 instrument and the PL (photoluminescence) spectrum of the compound was measured using a Jasco FP-8500 instrument.

On the other hand, with respect to the OLED compound of the present invention and CBP (4,4'-di (9H-carbazol-9-yl) -1,1'- biphenyl) (Photoluminescence) spectrum at 77 K was measured and shown in FIG. 5 and FIG.

division UV ^{* 1)}
(nm) PL ^{* 2)}
(nm, room temperature) Triplet energy ^{* 3)}
(eV, 77K) Compound 3-1
(DC1A-md-C3) 240, 293, 340 375 3.0 Compound 3-2
(C1A-md-DC3) 228, 239, 294 377 3.0 Compound 3-3
(C3A-md-DC3) 226, 238, 261, 300, 333 373 3.0 * 1) 1.0 x 10 ^-5 M in Methylene Chloride
2) 5.0 × 10 ^-5 M in Methylene Chloride
3) 1.0 x ^10-6 M in 2-Methyltetrahydrofuran

The OLED compound of the present invention has a triplet energy of 3.0 eV or more. Therefore, it has higher triplet energy than CBP used as the host material of the conventional light emitting layer, which can prevent the energy reversal phenomenon from the host material to the dopant.

Device fabrication test example

2-TNATA as a hole injection layer, NPB as a hole transport layer, CBP as a host of a light emitting layer, (PPy) ₃ Ir as a green phosphorescent dopant, Alq ₃ as an electron transport layer , Liq as an electron injection layer, and Al as a cathode. The structures of these compounds are shown below.

Comparative test example  : ITO (180 nm) / 2- TNATA ( 80 nm ) / NPB ( 10 nm ) / CBP: 15%  (PPy) ₃ Ir (40 nm) / Alq ₃ ( 35 nm ) / Liq ( 2 nm ) / Al ( 100 nm )

A blue fluorescent organic light-emitting device was prepared in the same manner as ITO (180 nm) / 2-TNATA (80 nm) / NPB (10 nm) / CBP: (PPy) ₃ Ir 15% (40 nm) / Alq ₃ nm) / Al (100 nm) in this order.

Before deposition of the organic material, the ITO electrode was subjected to oxygen plasma treatment for 2 minutes at 125 W at 2 ^-2 Torr. Organic materials were deposited at a vacuum of 9 ^-7 Torr. Co-deposition was performed at 0.1 Å / sec for Liq and 0.18 Å / sec for host (CBP) and 0.02 Å / sec for (PPy) ₃ Ir. sec. < / RTI > CBP was selected as the host material used in the experiment.

After fabricating the device, it was encapsulated in a glove box filled with nitrogen gas to prevent contact between air and moisture in the layer constituting the device. After forming barrier ribs with 3M's adhesive tape, Barium Oxide, a hygroscopic agent capable of removing moisture, was placed in a glass plate.

Test Example 1 ITO (180 nm) / 2-TNATA (60 nm) / NPB (10 nm) / (DC1A-md-C3): 15% (PPy) ₃ Ir (40 nm) / Alq ₃ (35 nm) / Liq (2 nm) / Al (100 nm)

In the above comparative test example, a device was fabricated in the same manner as in the above Comparative Test Example except that CBP was used instead of Compound 3-1 (DC1A-md-C3) prepared in Example 1 above as an electron transport layer.

Test Example 2 ITO (180 nm) / 2-TNATA (80 nm) / NPB (10 nm) / (C1A-md-DC3): 15% ₃ Ir (40 nm) / Alq ₃ (35 nm) / Liq (2 nm) / Al (100 nm)

In the comparative test example, a device was fabricated in the same manner as in the comparative test except that CBP was used instead of Compound 3-2 (C1A-md-DC3) prepared in Example 1 above as an electron transport layer.

Test Example 3 ITO (180 nm) / 2-TNATA (80 nm) / NPB (10 nm) / (C3A-md-DC3): 15% ₃ Ir (40 nm) / Alq ₃ (35 nm) / Liq (2 nm) / Al (100 nm)

In the comparative test example, a device was fabricated in the same manner as in the comparative test except that CBP was used instead of Compound 3-3 (C3A-md-DC3) prepared in Example 1 as an electron transport layer.

division compound The driving voltage (V) Efficiency (cd / A) Life (hr) Comparative Example CBP 3.5 35.17 3.8 Test Example 1 DC1A-md-C3 3.0 63.64 8.0 Test Example 2 C1a-md-DC3 2.9 57.15 14.5 Test Example 3 C3A-md-DC3 3.0 50.26 6.1

From the results shown in Table 2, the carbazole and carbene-substituted arylamine derivative compounds according to the present invention can be used as a material for an organic material layer of an organic electronic device including an organic electroluminescent device, The organic electroluminescent devices including the organic electroluminescent devices exhibit excellent characteristics in terms of efficiency, driving voltage, and stability.

In particular, the compounds according to the present invention exhibited high efficiency and characteristics due to excellent energy transfer from the host to the dopant.

Claims (10)

An arylamine derivative including a carbazole and a carbene represented by the following formula (1).
[Chemical Formula 1]

[In the formula 1,
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are each independently hydrogen, substituted or unsubstituted C ₁ -C ₃₀ alkyl, substituted or unsubstituted C ₃ -C ₃₀ cycloalkyl, Substituted or unsubstituted C ₆ -C ₃₀ aryl, substituted or unsubstituted C ₆ -C ₃₀ aralkyl, substituted or unsubstituted C ₁ -C ₃₀ heteroalkyl, substituted or unsubstituted C ₂ -C ₃₀ hetero Cycloalkyl, substituted or unsubstituted C ₅ -C ₃₀ heteroaryl, substituted or unsubstituted C ₅ -C ₃₀ heteroaralkyl,
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ adjacent to each other in one ring are each a substituted or unsubstituted C ₃ -C ₂₀ alkylene or a substituted or unsubstituted C ₃ -C ₂₀ alkenylene They may be connected to each other to form a fused ring,
p, q, r, s, t and u are integers of 1 to 4,
X ₁ , X ₂ and X ₃ are each independently selected from CH or N, and at least one of them is N.] The method according to claim 1,
The compound represented by Formula 1 is an arylamine derivative including a carbazole and a carbene selected from the structures of Formula 2 below.
(2)

Wherein R ₁ , R ₂ , R ₄ , R ₅ and R ₆ are the same as defined in the above formula (1). The method according to claim 1,
Wherein the carbazole and the carbene-substituted arylamine derivative of Formula 1 are selected from the group consisting of Formula 3 below.
(3)

An organic electroluminescent device comprising a carbazole and an arylamine derivative substituted with a carbene according to any one of claims 1 to 3. 5. The method of claim 4,
Wherein the carbazole and an arylamine derivative substituted with a carbene are used as a hole injection layer material or a hole transport layer material. 5. The method of claim 4,
Wherein said carbazole and carbene substituted arylamine derivatives are used as host materials for fluorescent and phosphorescent devices that emit blue, green, and red, respectively. A first electrode, a second electrode, and at least one organic layer disposed between the electrodes,
Wherein the organic material layer comprises the arylamine derivative of any one of claims 1 to 3. 8. The method of claim 7,
The organic material layer may include a hole injecting layer, a hole transporting layer, a functional layer having a hole injecting function and a hole transporting function simultaneously, a buffer layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, And at least one layer selected from the group consisting of a functional layer having a function at the same time. 8. The method of claim 7,
Wherein the arylamine derivative is contained in at least one selected from the group consisting of a light emitting layer, an organic material layer disposed between the anode and the light emitting layer, and an organic material layer disposed between the light emitting layer and the cathode. 8. The method of claim 7,
Wherein the arylamine derivative is contained in at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, and a functional layer having both a hole injecting function and a hole transporting function.

Images