KR20130074803A - Novel compounds having arcridine structure and organic electroluminescence device using the same - Google Patents

Abstract

PURPOSE: A novel compound containing an acridine structure is provided to ensure excellent brightness, power efficiency, heat resistance, and hole transporting and injecting performance, to enhance color purity and light emitting efficiency, and to be applied to a hole injection layer, a hole transport layer, and a light emitting layer of an organic electroluminescent device. CONSTITUTION: A compound is denoted by chemical formula 1. An organic electroluminescent device contains an anode, a cathode, and one or more organic layers inserted between the anode and the cathode. One or more organic layers contain the compound. The organic layer is a light emitting layer.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound containing an acridine structure and an organic electroluminescent device using the same. BACKGROUND ART < RTI ID = 0.0 > [0002]

The present invention relates to a novel compound including an acridine structure, a compound for an organic electroluminescent device using the same, and an organic electroluminescent device using the same, and more particularly, to a light emitting efficiency and luminance including a novel compound including an acridine structure. The present invention relates to an organic EL device having improved thermal stability, driving voltage, and lifespan.

Recently, as the development of the information and communication industry is accelerated, higher performance is required in the field of display devices, which is one of the most important fields. Such displays can be divided into luminescent and non-luminescent. Examples of displays belonging to the light emitting type include a cathode ray tube (CRT), an electroluminescence display (ELD), a light emitting diode (LED), a plasma display panel (PDP) have. Non-light emitting displays include liquid crystal displays (LCDs).

Generally, organic electroluminescent phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electroluminescent device using organic electroluminescent phenomenon generally has a structure including an anode and a cathode and an organic layer between them. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

A study on the electro luminescent (EL) devices which led to the blue electroluminescence using the anthracene single crystal in 1965 based on the observation of the organic thin film emission of the 1950s Bernanose was carried out in 1987 by Tang in the function of the hole layer and the luminescent layer Layered organic EL device has been proposed. In order to make a high efficiency and high number of organic electroluminescent devices, each organic material layer has been developed into a form of introducing characteristic organic material layers, and the development of specialized materials used thereon has been continued .

In the structure of such an organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the anode and electrons are injected into the organic layer at the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. A material used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material according to functions.

The luminescent material can be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary for realizing better natural colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the color purity and increase the luminous efficiency through energy transfer. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

It is reported that the organometallic complexes, which have relatively high stability and electron transfer rate, are good candidates for organic monomolecular materials, and that Alq3, which has excellent stability and electron affinity, is the most excellent. . Examples of conventionally known electron transport materials include flavon derivatives disclosed in Sanyo, or germanium and silicon cyclopentadiene derivatives of Chisso. (Japanese Unexamined Patent Publication No. 1998-017860, Japanese Unexamined Patent Publication No. 1999-087067).

Much research has been conducted on quinoline complex derivatives to date and many materials have been developed and commercialized since the DPVBi (formula A) of Idemitsu-Gosan as a blue light emitting layer material, and the blue material system of Idemitsu- And dinaphthylanthracene (Formula B) are known, but many research and development efforts are still required.

(A)

[Formula B]

In addition, organic monomolecular materials having an imidazole group, an oxazole group, and a thiazole group have been reported as conventional electron injecting materials and electron transporting materials. However, it has been reported that metal complex compounds of these materials are applied to a blue light emitting layer or a cyan light emitting layer of an organic electroluminescent device before such materials are reported as materials for electron transporting.

In particular, the doping material has been difficult to develop due to the material having a great influence on the improvement of the luminous efficiency, the luminous efficiency and the mismatch with the host material. In the case of the blue dopant, the styryl structure is not thermally stable, and thus it is difficult to increase the purity. Accordingly, color purity is lowered, efficiency is lowered, or the life is shortened. In addition, in order to have a deep blue color purity, the band gap between Homo and Lumo of the dopant needs to be large. Therefore, research and development is urgent about color purity, efficiency and thermal stability.

1. Japanese Laid-Open Patent Publication No. 1998-017860 2. Japanese Laid-Open Patent Application No. 1999-087067

The present invention provides a novel organic compound having improved various characteristics such as color purity, luminous efficiency, luminance, power efficiency, thermal stability, driving voltage, heat resistance, and device lifetime.

The present invention is to provide an organic electroluminescent device including the novel organic compound exhibiting high color purity, excellent color stability, low driving voltage and high efficiency.

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

A and B are each independently selected from a single bond, a substituted or an aryl group of a beach C ₆ ~ C ₆₀ ring, and a substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group consisting of a ring;

n is 0 or 1 except when A and B are simultaneously a single bond when n is 0;

Ar ₁ and Ar ₂ are each independently selected from the group consisting of Formula 2 to Formula 4, except that Ar ₁ and Ar ₂ are simultaneously Formula 4;

[Formula 2]

(3)

[Formula 4]

Each of R ₁ to R ₁₀ independently represents a substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₂ to C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₆₀ alkynyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted C ₃ to C ₆₀ heteroaryl group, a substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₇ ~ C ₆₀ aryl group, a substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group, a substituted or unsubstituted C ₃ ~ cycloalkyl group of C ₆₀ of the , A substituted or unsubstituted C ₁ to C ₆₀ halogenalkyl group, a substituted or unsubstituted C ₁ to C ₆₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ alkylsilyl group, a substituted or unsubstituted A C ₃ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₁ to C ₆₀ heteroarylsilyl group;

R ₁ to R ₈ may each be fused or may form a ring with adjacent substituents;

X ₁ to X ₅ are each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, Substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group, substituted or unsubstituted C ₁ An alkoxy group of -C ₆₀ , a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₆₀ arylamino group, Substituted or unsubstituted C ₆ -C ₆₀ diarylamino group, substituted or unsubstituted C ₃ -C ₆₀ heteroarylamino group, substituted or unsubstituted C ₂ -C ₆₀ diheteroarylamino group, substituted or unsubstituted C ₇ -C ₆₀ arylalkyl group, substituted or unsubstituted C ₃ -C ₆₀ heteroarylalkyl group, substituted or unsubstituted C ₃ -C ₆₀ A substituted or unsubstituted C ₁ to C ₆₀ halogenoalkyl group, a substituted or unsubstituted C ₁ to C ₆₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₆₀ alkyl group, A substituted C ₃ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₁ to C ₆₀ heteroarylsilyl group;

p, q, r, s and t are each independently an integer of 0 to 4;

According to the present invention, at least one of Ar ₁ and Ar ₂ is represented by the following formula (2a).

(2a)

According to the present invention, at least one of Ar ₁ and Ar ₂ is represented by the following general formula (3a) or (3b).

[Chemical Formula 3]

(3b)

According to the present invention, the substituted or unsubstituted C ₆ to C ₆₀ aryl group and the substituted or unsubstituted C ₃ to C ₆₀ heteroaryl group selected as A and B are each independently substituted or unsubstituted phenyl , Substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, Substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted triazine, substituted or unsubstituted quinoline, substituted or unsubstituted quinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted carbazole , And a substituted or unsubstituted phenanthroline, and each substituent used in the substitution is a C ₁ -C ₅ alkyl group or a C ₁ -C ₅ alkyl group substituted with a halogen element .

According to the present invention, R ₁ , R ₄ , R ₉ And substituted is selected as R _10, or unsubstituted C ₆ ~ C ₆₀ aryl group, and a group heteroaryl substituted or unsubstituted C ₃ ~ C _60, each independently represent a substituted or unsubstituted phenyl, substituted or unsubstituted ring Biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted Substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, Substituted or unsubstituted isoquinolines, and substituted or unsubstituted carbazoles, and each of the substituents used for the substitution is selected from the group consisting of a C ₁ to C ₅ alkyl group or a C ₁ to C ₅ substituted egg Characterized in that group.

According to the present invention, there is provided 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, The organic electroluminescent device includes the compound according to any one of claims 1 to 5.

According to the invention, the organic electroluminescent device is characterized in that it comprises a compound according to the invention described above in the light emitting layer.

The compound represented by the formula (1) according to the present invention is excellent in luminance, power efficiency, heat resistance, hole transporting ability and hole injection performance, and can exhibit an increase in color purity and luminous efficiency, A light-emitting layer, a light-emitting layer, a light-emitting layer, and a light-emitting layer.

The organic electroluminescent device including the compound represented by Chemical Formula 1 according to the present invention exhibits low driving voltage and high efficiency, and thus has an excellent effect on maximizing performance and improving lifetime in the organic light emitting device panel.

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

In order to accomplish the above object, the present invention is a novel compound containing an acridine structure and an organic electroluminescent device using the same. More particularly, the present invention relates to a blue organic electroluminescent device which is improved in luminous efficiency and luminance, prolongs its lifetime and is excellent in thermal stability by using it as a dopant of an organic light emitting layer (EML) of a multilayer organic electroluminescent device . Hereinafter, the configuration of the present invention will be described in more detail.

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

A and B are each independently selected from a single bond, a substituted or an aryl group of a beach C ₆ ~ C ₆₀ ring, and a substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group consisting of a ring;

n is 0 or 1 except when A and B are simultaneously a single bond when n is 0;

Ar ₁ and Ar ₂ are each independently selected from the group consisting of Formula 2 to Formula 4, except that Ar ₁ and Ar ₂ are simultaneously Formula 4;

[Formula 2]

(3)

[Formula 4]

Each of R ₁ to R ₁₀ independently represents a substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₂ to C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₆₀ alkynyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted C ₃ to C ₆₀ heteroaryl group, a substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₇ ~ C ₆₀ aryl group, a substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group, a substituted or unsubstituted C ₃ ~ cycloalkyl group of C ₆₀ of the , A substituted or unsubstituted C ₁ to C ₆₀ halogenalkyl group, a substituted or unsubstituted C ₁ to C ₆₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ alkylsilyl group, a substituted or unsubstituted A C ₃ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₁ to C ₆₀ heteroarylsilyl group;

R ₁ to R ₈ may each be fused or may form a ring with adjacent substituents;

X ₁ to X ₅ are each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, Substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group, substituted or unsubstituted C ₁ An alkoxy group of -C ₆₀ , a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₆₀ arylamino group, Substituted or unsubstituted C ₆ -C ₆₀ diarylamino group, substituted or unsubstituted C ₃ -C ₆₀ heteroarylamino group, substituted or unsubstituted C ₂ -C ₆₀ diheteroarylamino group, substituted or unsubstituted C ₇ -C ₆₀ arylalkyl group, substituted or unsubstituted C ₃ -C ₆₀ heteroarylalkyl group, substituted or unsubstituted C ₃ -C ₆₀ A substituted or unsubstituted C ₁ to C ₆₀ halogenoalkyl group, a substituted or unsubstituted C ₁ to C ₆₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₆₀ alkyl group, A substituted C ₃ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₁ to C ₆₀ heteroarylsilyl group;

p, q, r, s and t are each independently an integer of 0 to 4;

The compound represented by formula (1) of the present invention can be represented by the following formula.

In the above formulas, R ₁ to R ₁₀ are the same as defined in the above formula (1), and R ₁ 'to R ₈ ' are the same as R ₁ to R ₈ .

R ₁ to R ₈ , R ₁ 'to R ₈ ', R ₉ and R ₁₀ are the same as or different from each other, and each independently represents a substituent ≪ / RTI > However, it is not limited to the substituents exemplified below.

The following compounds are representative examples of the compound represented by the formula (1) of the present invention, but the compounds represented by the formula (1) of the present invention are not limited thereto.

The compound represented by the formula (1) of the present invention can be synthesized according to a general synthesis method, and the detailed synthesis process of the compound of the present invention will be described concretely in a synthesis example described later.

More preferably, the compound according to the present invention is a compound represented by the general formula (1), wherein at least one of Ar ₁ and Ar ₂ is represented by the following general formula (2a).

(2a)

More preferably, at least one of Ar ₁ and Ar ₂ in the compound represented by Formula 1 is represented by Formula 3a or Formula 3b.

[Chemical Formula 3]

(3b)

More preferably, the substituted or unsubstituted C ₆ to C ₆₀ aryl group and the substituted or unsubstituted C ₃ to C ₆₀ heteroaryl group selected from A and B in the compound represented by the general formula (1) Substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridine , Substituted or unsubstituted pyrimidine, substituted or unsubstituted pyridazine, substituted or unsubstituted pyrazine, substituted or unsubstituted triazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted quinox Substituted or unsubstituted carbazoles, and substituted or unsubstituted phenanthrolines, wherein each substituent used in the substitution is selected from the group consisting of an unsubstituted C ₁ -C ₅ alkyl group or a And is a C ₁ - C ₅ alkyl group substituted with a halogen atom.

More preferably, in the compound represented by Formula 1, the R_One, R₄, R₉ And R₁₀Substituted or unsubstituted C selected by₆~ C₆₀Aryl groups and substituted or unsubstituted C₃~ C₆₀Each heteroaryl group is independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or Unsubstituted fluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted triazine, substituted or unsubstituted pyridazine, substituted or unsubstituted Substituted pyrazine, substituted or unsubstituted benzimidazole, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, and substituted or unsubstituted carbazole, each of the substituents used for the above substitution Silver c_One~ C₅C substituted with an alkyl group or halogen element of_One~ C₅It is characterized by the alkyl group.

Another aspect of the present invention relates to an organic electroluminescent device including a compound represented by Formula 1, more specifically, a compound described above in Formula 1 to Formula 4 above.

Specifically, the present invention is an organic light emitting device comprising an anode (anode), a cathode (cathode), and at least one organic layer interposed between the anode and the cathode, at least one of the organic layer is It provides an organic electroluminescent device comprising a compound represented by the formula (1).

More preferably, the organic electroluminescent device is characterized in that any one or more of Ar ₁ and Ar ₂ in the formula (1) comprises a compound of the formula (2a).

More preferably, the organic electroluminescent device is characterized in that at least one of Ar ₁ and Ar ₂ in Formula 1 includes the compound of Formula 3a or Formula 3b.

More preferably, the organic electroluminescent device further comprises a substituted or unsubstituted C ₆ to C ₆₀ aryl group and a substituted or unsubstituted C ₃ to C ₆₀ heteroaryl group selected from A and B in the above formula Substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted pyrimidines, substituted or unsubstituted pyridazines, substituted or unsubstituted pyrazines, substituted or unsubstituted triazines, substituted or unsubstituted quinolines, substituted or unsubstituted isoquinolines, substituted or unsubstituted pyrazines, substituted or unsubstituted pyrazines, quinoxaline, a substituted or unsubstituted carbazole, and a substituted or unsubstituted, is selected from the group consisting of phenanthroline, an alkyl group of each substituent used in the substituted is unsubstituted C ₁ ~ C ₅ ring again It characterized in that it comprises a C alkyl group of ₁ ~ C ₅ substituted with a halogen atom.

More preferably, the organic electroluminescent device is a compound represented by formula (1) wherein R ₁ , R ₄ , R ₉ And substituted is selected as R _10, or unsubstituted C ₆ ~ C ₆₀ aryl group, and a group heteroaryl substituted or unsubstituted C ₃ ~ C _60, each independently represent a substituted or unsubstituted phenyl, substituted or unsubstituted ring Biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted Substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, Substituted or unsubstituted isoquinolines, and substituted or unsubstituted carbazoles, and each of the substituents used for the substitution is selected from the group consisting of a C ₁ to C ₅ alkyl group or a C ₁ to C ₅ substituted egg It characterized by including the resulting compound.

In this case, the organic electroluminescent device may include two or more compounds of the same or different types.

The organic material layer containing the compound represented by Formula 1 of the present invention may be any one or more of the hole injection layer 103, the hole transport layer 104, the electron injection layer 108, the electron transport layer 107, . In this case, the organic electroluminescent device can maximize the hole injecting ability, the electron transporting ability, and the electron injecting ability. Further, by using it as a light emitting layer material of an organic electroluminescent device, it is possible to provide a further improved efficiency, drive characteristics and lifetime (see FIG. 1).

More preferably, the organic compound layer containing the above-mentioned compound is an organic electroluminescent device characterized by containing the compound as a dopant as a light emitting layer.

In the present invention, the light emitting layer may comprise a fluorescent guest material. Preferably, the compound represented by Formula 1 is included in the organic light emitting device as a blue, green and / or red phosphorescent host, fluorescent host, hole transport material and / or hole transport, electron transport material and / .

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. At least one of the light emitting layer, the hole injecting layer, and the hole transporting layer may include the compound represented by Formula 1. An electron injection layer may be disposed on the electron transport layer.

In addition, the organic light emitting device according to the present invention may have an insulating layer or an adhesive layer interposed between the electrode and the organic material layer as well as the structure in which the anode, one or more organic layers and the cathode are sequentially stacked, as described above.

In the organic light emitting device of the present invention, the organic material layer containing the compound of Formula 1 may be formed by a vacuum evaporation method or a solution coating method. Examples of the application of the solution 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 can be manufactured by using a conventional material and method known in the art, except that at least one layer of the organic material layer includes the compound represented by the above formula (1) ≪ / RTI >

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

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 metal and oxides 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.

The hole injecting layer, the hole transporting layer, and the electron injecting layer are not particularly limited, and conventional materials known in the art can be used.

Hereinafter, the present invention will be described in more detail with reference to Examples. It should be understood, however, that these examples are for illustrative purposes only and are not to be construed as limiting the scope of the present invention.

One. Preparation Example  Synthesis of A Ar )

1. 1. Preparation Example  Synthesis of A1

To a 2 L round bottom flask was added 31.4 g (150 mmol) of 9,9-dimethyl-9,10-dihydroacridine and 23.5 g (1 equivalent) of bromobenzene, 42.7 g (three equivalents) of sodium tert-butoxide and 2.55 g (dibenzylideneacetone) dipalladium 2.5 mol (3 mol%) of 1,1-bis (diphenylphosphino) ferrocene was added under nitrogen atmosphere and then refluxed in 750 ml of toluene over night. After completion of the reaction, the reaction solution was filtered through Celite, and 34 g (yield 80%) of 9,9-dimethyl-10-phenyl-9,10-dihydroacridine was obtained through column chromatography.

34 g (105 mmol) of 9,9-dimethyl-10-phenyl-9,10-dihydroacridine synthesized above and 19 g (1 equivalent) of n-bromosuccinimide were stirred in a 2 L round flask with 500 ml of carbon tetrachloride for 3 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was filtered through a Celite column, and 23 g (yield: 60%) of 2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine of Preparation Example A1 was obtained through column chromatography.

1. 2. Preparation Example  Synthesis of A2

60.2 g (200 mmol) of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-ol, 30 ml of toluene, and 79.0 g of pyridine (5 equivalents) were added to a 2 L round-bottomed flask and lowered to 0? 62.0 g (1.1 equiv) of anhydride was added and left for 30 minutes. After that, the reaction mixture was stirred at room temperature for 4 hours, and water was added thereto to terminate the reaction. After the reaction solution was separated, the obtained organic layer was washed with water, 5% hydrochloric acid and dried over anhydrous magnesium sulfate. 71.8 g (180 mmol) (yield: 90%) of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl sulfochloridate was obtained from the organic layer obtained above.

71.8 g (180 mmol) of the 9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl sulfochloridate synthesized above, 55.7 g (1.2 equivalent) of 2-acetoxy-4-bromophenylboronic acid, 85.8 g (4.5 eq.) of disodium carbonate were placed in a 2 L round-bottomed flask and 2.1 g (1 equivalent) of Pd (PPh3) 4 was added under nitrogen atmosphere and the mixture was stirred under refluxing conditions for 4 hours. After cooling to room temperature, the organic layer was separated from the reaction solution, washed with water, and dried over anhydrous magnesium sulfate. The resulting residue was purified by column chromatography to obtain 70.1 g (yield 81%) of 1- (5-bromo-2- (9,9-dimethyl-10-phenyl-9,10-dihydroacridin- ≪ / RTI >

2L of nitrogen-substituted THF 500ml in 70.1g (146mmol) of 1- (5-bromo-2- (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) phenyl) ethanone synthesized above It put in the flask and heated up to 50 ?. 250 ml of a solution of toluene and THF in a ratio of 3: 1 to 24.3 g (1.4 equivalents) of methylmagnesium bromide was slowly mixed in the reactor for 1 hour in a nitrogen atmosphere, followed by stirring at 50 ° C for 3 hours. After cooling to room temperature, water was added to the reaction solution to complete the reaction, followed by washing and drying with anhydrous magnesium sulfate. 58.0 g (yield 80%) of 2- (5-bromo-2- (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) phenyl) propan-

58.0 g (117 mmol) of 2- (5-bromo-2- (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) phenyl) propan- 24.9 g (1.5 eq.) Of trifluoroborone diethylether were added to a nitrogen-substituted 2 L flask, and the mixture was stirred for 10 minutes under a nitrogen atmosphere. Thereafter, the reaction mixture was finished up to 50 ° C. and stirred for 2 hours. After cooling to room temperature, the organic layer was washed with water, and the obtained organic layer was dried over anhydrous magnesium sulfate. The residue obtained after concentration was purified by column chromatography and recrystallized to obtain the compound of Preparation A2, 9-bromo-7,7,13,13-tetramethyl-5-phenyl-7,13-dihydro- b] acridine (yield: 40%).

1.3. Preparation Example  Synthesis of A3

Preparative Example A3 The compound 9-bromo-13,13-dimethyl-5,7,7-triphenyl-7,13-dihydro was synthesized by the same method except that phenylmagnesium bromide was used instead of methylmagnesium bromide in the synthesis of A2. -5H-indeno [1,2-b] acridine.

1.4. Preparation Example  Synthesis of A4

Preparative Example Preparation Example A4 Preparation 2-bromo-9,9-dimethyl-10- (naphthalen-2-yl) -9, 2-bromo- 10-dihydroacridine.

1.5. Preparation Example  Synthesis of A5

9,9-dimethyl-10- (naphthalen-2-yl) -9,10-dihydroacridin-2 was used in place of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin- -ol was used to prepare the compound 9-bromo-7,7,13,13-tetramethyl-5- (naphthalen-2-yl) -7,13-dihydro- indeno [1,2-b] acridine.

1.6. Preparation Example  Synthesis of A6

Preparation Example A6 Synthesis was carried out in the same manner except that 1-bromo-4-tert-butylbenzene was used instead of bromobenzene in the synthesis process A1. Preparation Example A6 Synthesis of 2-bromo-10- (4-tert-butylphenyl) 9-dimethyl-9,10-dihydroacridine.

1.7. Preparation Example  Synthesis of A7

10- (4-tert-butylphenyl) -9,9-dimethyl-9,10-dihydroacridin-2 instead of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-ol in the synthesis of Preparation Example A2 Synthesis Example 5 Preparation of A7 Compound 9-bromo-5- (4-tert-butylphenyl) -7,7,13,13-tetramethyl-7,13-dihydro-5H- indeno [1,2b] acridine was obtained.

1.8. Preparation Example  Synthesis of A8

Preparative Example Preparation Example A8 Synthesis of compound 10- (biphenyl-4-yl) -2-bromo-9,9-dimethyl-9,10-dibromobenzene was carried out by the same method except that 4-bromobiphenyl was used instead of bromobenzene in the synthesis of A1. 10-dihydroacridine.

1.9. Preparation Example  Synthesis of A9

(Biphenyl-4-yl) -9,9-dimethyl-9,10-dihydroacridin-2 was used in place of 9,9-dimethyl-10-phenyl-9,10-dihydroacridin- -ol was used instead of the compound of Preparation Example A9 to prepare the compound 5- (biphenyl-4-yl) -9-bromo-7,7,13,13-tetramethyl-7,13-dihydro- indeno [1,2-b] acridine.

Preparation Example A1 In the synthesis process A1, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ were removed by using bromobenzene instead of bromobenzene, 3-bromobiphenyl, 2-bromophenanthrene, 2-bromo-9,9- R ₄ may be prepared in different preparations. However, the substituents listed above are only illustrative of the present invention, and the preparation examples of the present invention are not limited by the preparation examples (Ar).

2. Preparation of compounds

2.1. Preparation of Compound (1)

Synthesis Example 1-1) Preparation of Compound 1-1

Preparation Example 1 A compound (2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine) 10.0 g (27.6 mmol) was dissolved in 200 mL of tetrahydrofuran, and n-BuLi (1.6 M at -78 ° C) was prepared. in n-Hexane) 28.8 mL (24.0 mmol) was slowly added dropwise. After stirring for 30 minutes, 1.8 mL (1.2 eq.) Of N, N-dimethylformamide was added. The reaction was terminated by adding an aqueous solution of NH4Cl and distilled water, and the organic layer was separated and removed under reduced pressure. The residue was recrystallized from methanol: n-hexane (1: 1) 10-phenyl-9,10-dihydroacridine-2-carbaldehyde (yield: 75%).

6.48 g (20.7 mmol) of compound 9,9-dimethyl-10-phenyl-9,10-dihydroacridine-2-carbaldehyde, 0.9 g (1.5 equivalents) of NaBH4 were dissolved in 80 mL of tetrahydrofuran, and cooled to 0 40 mL of methanol was slowly added dropwise. After stirring for 30 minutes, distilled water was added to complete the reaction. The reaction mixture was extracted with ethyl acetate, dried under reduced pressure, and purified by column chromatography (dichloromethane / hexane = 1/1) to obtain 9,9- dihydroacridin-2-yl) methanol 3.24 g (10.36 mmol) (yield 50%).

3.24 g (10.36 mmol) of the compound (9,9-dimethyl-10-phenyl-9,10-dihydroacridin-2-yl) methanol obtained above was dissolved in 80 mL of triethylphosphite under a nitrogen stream . 40 mL of triethylphosphite was added to another reaction vessel, the lid was opened, and 3.6 g (1 equivalent) of iodine was added thereto, followed by stirring at 0 ° for 30 minutes. Thereafter, the temperature was raised to 150 ° C, followed by stirring for 4 hours. After completion of the reaction, triethyl phosphite was removed by distillation under reduced pressure, and the residue was washed with distilled water, extracted with ethyl acetate, dried under reduced pressure, and purified by column chromatography (ethyl acetate / hexane = 1/1) mmol) (yield: 85%).

Synthesis Example 1-2) Preparation of Compound 1-2

Dissolve 5.0 g (20.35 mmol) of diphenylamine in 100 mL of N, N-dimethylformamide, cool to 0 ° C, add 16 mL (203.8 mmol) of N, N-dimethylformamide to another container, and cool to 0 ° C. Was added slowly. The mixture was stirred for 30 minutes and then slowly added dropwise at 0 ° to a container in which triphenylamine was dissolved. The mixture was further stirred for 18 hours at 45 ° C., followed by slowly pouring a saturated aqueous sodium hydroxide solution and stirring with excess water. At this time, a solid was formed, which was filtered and washed with water and methanol to obtain 4.7 g (17.5 mmol) of the compound 1-2 (yield: 86%).

Synthesis Example 1-3) Preparation of Compound 1

3.82 g (8.80 mmol) of the compound 1-1 thus obtained and 2.46 g (8.80 mmol) of the compound 1-2 were placed in a reaction vessel, followed by drying under reduced pressure. After making nitrogen atmosphere, add 200 mL of tetrahydrofuran, dissolve it, cool it to 0 ° C and dissolve 1,46 g (1.5 eq) of potassium tert-butoxide (t-BuOK) in 10 mL of tetrahydrofuran and slowly add it dropwise. I did it. After stirring at 0 ° C. for 2 hours, 150 mL of distilled water was added thereto and stirred. At this time, a solid was formed, which was filtered under reduced pressure to obtain a solid. Washed with methanol and ethyl acetate, and recrystallized to obtain 2.52 g (5.28 mmol) of Compound 1 (yield: 60%).

Elemental Analysis: C, 87.83; H, 6.32; N, 5.85 HRMS [M] < ⁺ & gt ^; : 477

(M, 4H), 6.73-6.91 (m, 6H), 7.02 (d, IH) 2H), 7.20 (t, 6H), 7.47 (d, IH)

2.2. Preparation of Compound 2

Synthesis Example 2-1) Preparation of Compound 2-1

Synthesis Example 1-1 was synthesized in the same manner except that the compound of Preparation Example A2 was used instead of the preparation Example A1.

Synthesis Example 2-2) Preparation of Compound 2-2

Synthesis was carried out in the same manner as in Synthesis Example 1-2, except that N-phenylnaphthalen-2-amine was used instead of diphenylamine.

Synthesis Example 2-3) Preparation of Compound 2

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 2-1 and 2-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 89.40; H, 6.25; N, 4.34 HRMS [M] < ⁺ & gt ^; : 643

2.3. Preparation of Compound 3

Synthesis Example 3-1) Preparation of Compound 3-1

Was synthesized in the same manner as Synthesis Example 2-1.

Synthesis Example 3-2) Preparation of Compound 3-2

Preparation Example 1 A compound (2-bromo-9,9-dimethyl-10-phenyl-9,10-dihydroacridine) 10.0 g (27.6 mmol) was dissolved in 200 mL of tetrahydrofuran, and n-BuLi (1.6 M at -78 ° C) was prepared. in n-Hexane) 28.8 mL (24.0 mmol) was slowly added dropwise. After stirring for 30 minutes, 1.8 mL (1.2 equiv) of N, N-dimethyl formamide was added thereto. The reaction was terminated by adding an aqueous solution of NH4Cl and distilled water, and the organic layer was separated and removed under reduced pressure. The residue was recrystallized from methanol: n-hexane (1: 1) 10-phenyl-9,10-dihydroacridine-2-carbaldehyde (yield: 75%).

Synthesis Example 3-3) Preparation of Compound 3

Synthesis was conducted in the same manner as in Synthesis Example 1-3 except that the above-obtained Compounds 3-1 and 3-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 89.54; H, 6.52; N, 3.94 HRMS [M] < ⁺ & gt ^; : 709

2.4. Preparation of compound 4

Synthesis Example 4-1) Preparation of Compound 4-1

Preparation Example 1-1 was prepared in the same manner as Preparation Example A1, except that the compound of Preparation Example A4 was used instead of Preparation Example A1.

Synthesis Example 4-2) Preparation of Compound 4-2

Synthesis was carried out in the same manner as in Synthesis Example 1-2.

Synthesis Example 4-3) Preparation of Compound 4

Was synthesized in the same manner as in Synthesis Example 1-3 except that the above-obtained Compounds 4-1 and 4-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 88.60; H, 6.10; N, 5.30 HRMS [M] < ⁺ >: 527

2.5. Preparation of Compound 5

Synthesis Example 5-1) Preparation of Compound 5-1

Synthesis Example 1-1 was prepared in the same manner except that the compound of Preparation Example A7 was used instead of the preparation example A1.

Synthesis Example 5-2) Preparation of Compound 5-2

Synthesis was conducted in the same manner as in Synthesis Example 2-2.

Synthesis Example 5-3) Preparation of Compound 5

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the above-obtained Compounds 5-1 and 5-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 89.10; H, 6.90; N, 4.00 HRMS [M] < ⁺ & gt ^; : 699

2.6. Preparation of Compound 6

Synthesis Example 6-1) Preparation of Compound 6-1

Preparation Example 1-1 was prepared in the same manner as Preparation Example A-1 except that the compound of Preparation Example A8 was used instead of Preparation Example A1.

Synthesis Example 6-2) Preparation of Compound 6-2

Synthesis was carried out in the same manner as in Synthesis Example 1-2.

Synthesis Example 6-3) Preparation of Compound 6

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the compounds 6-1 and 6-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 88.77; H, 6. 18; N, 5.05. HRMS [M] < ⁺ & gt ^; : 553

2. 7 Preparation of Compound 7

Synthesis Example 7-1) Preparation of Compound 7-1

Synthesis was carried out in the same manner as in Synthesis Example 1-1.

Synthesis Example 7-2) Preparation of Compound 7-2

Synthesis was carried out in the same manner as in Synthesis Example 1-1.

Synthesis Example 7-3) Preparation of Compound 7

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the compounds 7-1 and 7-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 88.85; H, 6.44; N, 4.71 HRMS [M] < ⁺ & gt ^; : 593

2. 8. Preparation of compound 8

Synthesis Example 8-1) Preparation of Compound 8-1

Synthesis was carried out in the same manner as in Synthesis Example 1-1.

Synthesis Example 8-2) Preparation of Compound 8-2

Preparation Example 3-2-2 Preparation Example A1 Instead of Compound A1 The title compound was synthesized in the same way except that Compound A4 was used.

Synthesis Example 8-3) Preparation of Compound 8

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the compounds 8-1 and 8-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 89.40; H, 6.25; N, 4.34 HRMS [M] < ⁺ & gt ^; : 643

2. Preparation of 9

Synthesis Example 9-1) Preparation of Compound 9-1

Synthesis was conducted in the same manner as in Synthesis Example 5-1.

Synthesis Example 9-2) Preparation of Compound 9-2

Synthesis was conducted in the same manner as in Synthesis Example 3-2.

Synthesis Example 9-3) Preparation of Compound 9

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the above-obtained Compounds 9-1 and 9-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 89.25; H, 7.10; N, 3.65 HRMS [M] < ⁺ & gt ^; : 765

2.10. Preparation of Compound 10

Synthesis Example 10-1) Preparation of Compound 10-1

Was synthesized in the same manner as Synthesis Example 2-1.

Synthesis Example 10-2) Preparation of Compound 10-2

Preparation Example in Synthesis Example 3-2 The procedure of Preparation Example A1 was repeated except that the compound A5 was used in place of the compound A1.

Synthesis Example 10-3) Preparation of Compound 10

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the compounds 10-1 and 10-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.37; H, 6.43; N, 3.19 HRMS [M] < ⁺ & gt ^; : 875

3. Preparation Example  Synthesis of B Ar -A- Br  rescue)

3.1. Preparation Example  Synthesis of B1

To a 250 ml round-bottomed flask was added 6 g (16.5 mmol) of 9,9-dimethyl-10-phenyl-9,10-dihydroacridine, 5.1 g (1.2 equivalent) of bis (pinacolato) diboron, and 1,1 bis (diphenylphosphino) ferrocene dichloropalladium ) And potassium acetate (4.8 g, 3 equivalents) were added to 90 ml of 1,4-dioxane, and the mixture was stirred under reflux in an atmosphere of nitrogen over night. H ₂ O was added to terminate the reaction. Then, methylene chloride was added to separate the H ₂ O layer and the organic layer. After the solvent was removed under reduced pressure, the residue was purified by column chromatography to obtain 9,9-dimethyl-10-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- (13.2 mmol) of 9,10-dihydroacridine (yield 80%).

5.4 g (13.2 mmol) of 9,9-dimethyl-10-phenyl-2- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- , 2.1 g (5 mol%) of tetrakis (triphenylphosphine) palladium (0 mol) and 15 g (3 eq.) Of potassium carbonate were mixed with 61 ml of 1,4-dioxane and 18 ml of H2O in a 250 ml round- And the mixture was refluxed under nitrogen for 3 hours. After completion of the reaction, the reaction solution was subjected to column chromatography to obtain 4.63 g (10.56 mmol) (yield 80%) of 2- (4-bromophenyl) -9,9-dimethyl-10-phenyl-9,10- .

3.2. Preparation Example  Synthesis of B2

Preparation Example B1 Synthesis was carried out in the same manner except that 2,6-dibromonaphthalene was used instead of 1,4-dibromobenzene in the synthesis process.

3.3. Preparation Example  Synthesis of B3

Preparation Example B1 Synthesis was carried out in the same manner except that 4,4'-dibromobiphenyl was used instead of 1,4-dibromobenzene in the synthesis process.

3.4. Preparation Example  Synthesis of B4

Preparation Example B1 Using 2-bromo-9,9-dimethyl-10- (naphthalen-2-yl) -9,10-dihydroacridine instead of 9,9-dimethyl-10-phenyl-9,10-dihydroacridine , And 2,7-dibromo-9,9-dimethyl-9H-fluorene was used instead of 1,4-dibromobenzene.

3.5. Preparation Example  Synthesis of B5

Preparation Example B1 was repeated except that 9-dimethyl-10-phenyl-9,10-dihydroacridine was used instead of 10-bromo-7,7,13,13-tetramethyl-5-phenyl-7,13-dihydro- [L, 2-b] acridine. ≪ / RTI >

3.6. Preparation Example  Synthesis of B6

10-bromo-7,7,13,13-tetramethyl-5- (naphthalen-2-yl) -7,13-dihydroacridine was used in place of 9,9-dimethyl- -dihydro-5H-indeno [1,2-b] acridine and 2,7-dibromo-9,9-dimethyl-9H-fluorene instead of 1,4-dibromobenzene.

3.7. Preparation Example  Synthesis of B7

In the synthesis of Preparation B1, 10-bromo-5- (4-tert-butylphenyl) -7,7,13,13-tetramethyl-7,13 -dihydro-5H-indeno [1,2-b] acridine and using 2,6-dibromonaphthalene instead of 1,4-dibromobenzene.

4. Preparation of compounds

4.1. Preparation of Compound 11

Synthesis Example 11-1) Preparation of Compound 11-1

Preparation Example 1-1 was prepared in the same manner as Preparation Example A1, except that Preparation Example B1 was used instead of Preparation Example A1.

Synthesis Example 11-2) Preparation of Compound 11-2

1,4-dibromobenzene (5.13 g, 22.0 mmol) and diphenylamine (3.8 g, 22.6 mmol) were dissolved in 70 mL of toluene under a nitrogen atmosphere and then trisubenzylidine acetone dipalladium (0.4 g, 0.5 mmol) was added under nitrogen. Then, P (t-Bu) 3 (0.2 g, 0.9 mmol) was added to the reaction mixture, and NaOBut (2.6 g, 27.1 mmol) was added thereto and the reaction solution was refluxed for 24 hours. After the reaction was completed, the palladium was removed by hot filtration through a thin pad of silica gel and passed through a silica gel column at a ratio of hexane to dichloromethane 7: 3. The solvent was removed and vacuum drying was conducted to obtain 4-bromo-N, N-diphenylaniline (4.5 g, 19.3 mmol) (yield: 88%).

Preparative Example 3-2-2 4- (diphenylamino) benzaldehyde was obtained in the same manner as the compound 4-bromo-N, N-diphenylaniline obtained above instead of the compound A1.

Synthesis Example 11-3) Preparation of Compound 11

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 11-1 and 11-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 89.49; H, 6.07; N, 4.44 HRMS [M] < ⁺ & gt ^; : 629

4.2. Preparation of Compound 12

Synthesis Example 12-1) Preparation of Compound 12-1

Synthesis was carried out in the same manner as in Synthesis Example 1-1.

Synthesis Example 12-2) Preparation of Compound 12-2

Synthesis Example 11-2 was synthesized in the same manner except that 2,7-dibromo-9,9-dimethyl-9H-fluorene was used instead of 1,4-dibromobenzene.

Synthesis Example 12-3) Preparation of Compound 12

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 12-1 and 12-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 89.51; H, 6.31; N, 4.18 HRMS [M] < ⁺ & gt ^; : 669

4. Preparation of Compound 13

Synthesis Example 13-1) Preparation of Compound 13-1

Synthesis was conducted in the same manner as in Synthesis Example 4-1.

Synthesis Example 13-2) Preparation of Compound 13-2

Synthesis was conducted in the same manner as in Synthesis Example 12-2.

Synthesis Example 13-3) Preparation of Compound 13

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 13-1 and 13-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 89.96; H, 6. 15; N, 3.89 HRMS [M] < ⁺ & gt ^; : 719

4.4. Preparation of Compound 14

Synthesis Example 14-1) Preparation of Compound 14-1

Synthesis Example 1-1 was synthesized in the same manner except that 2-bromo-10- (4-tert-butylphenyl) -9,9-dimethyl-9,10-dihydroacridine was used instead of Preparation A1 compound.

Synthesis Example 14-2) Preparation of Compound 14-2

Synthesis was conducted in the same manner as in Synthesis Example 12-2.

Synthesis Example 14-3) Preparation of Compound 14

Was synthesized in the same manner as in Synthesis Example 1-3 except that the above-obtained Compounds 14-1 and 14-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 89.21; H, 6.93; N, 3.85 HRMS [M] < ⁺ & gt ^; : 725

4.5. Preparation of compound 15

Synthesis Example 15-1) Preparation of Compound 15-1

Was synthesized in the same manner as Synthesis Example 2-1.

Synthesis Example 15-2) Preparation of Compound 15-2

Synthesis was conducted in the same manner as in Synthesis Example 12-2.

Synthesis Example 15-3) Preparation of Compound 15

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 15-1 and 15-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.04; H, 6.40; N, 3.56 HRMS [M] < ⁺ & gt ^; : 785

4.6. Preparation of Compound 16

Synthesis Example 16-1) Preparation of Compound 16-1

Synthesis was conducted in the same manner as in Synthesis Example 5-1.

Synthesis Example 16-2) Preparation of Compound 16-2

Synthesis Example 11-2 was synthesized in the same manner except that 4,4'-dibromobiphenyl was used instead of 1,4-dibromobenzene.

Synthesis Example 16-3) Preparation of Compound 16

Synthesis was conducted in the same manner as in Synthesis Example 1-3 except that the above-obtained Compounds 16-1 and 16-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 89.73; H, 6. 78; N, 3.49 HRMS [M] < ⁺ & gt ^; : 801

4.7. Preparation of Compound 17

Synthesis Example 17-1) Preparation of Compound 17-1

Synthesis was conducted in the same manner as Synthesis Example 11-1.

Synthesis Example 17-2) Preparation of Compound 17-2

Synthesis was carried out in the same manner as in Synthesis Example 1-2.

Synthesis Example 17-3) Preparation of Compound 17

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 17-1 and 17-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 88.77; H, 6. 18; N, 5.05. HRMS [M] < ⁺ & gt ^; : 553

4.8. Preparation of Compound 18

Synthesis Example 18-1) Preparation of Compound 18-1

Preparation Example 1-1 was prepared in the same manner as Preparation Example B-1 except that the compound of Preparation Example B4 was used instead of Preparation Example A1.

Synthesis Example 18-2) Preparation of Compound 18-2

Synthesis was conducted in the same manner as in Synthesis Example 2-2.

Synthesis Example 18-3) Preparation of Compound 18

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 18-1 and 18-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 89.96; H, 6. 15; N, 3.89 HRMS [M] < ⁺ & gt ^; : 719

4.9. Preparation of Compound 19

Synthesis Example 19-1) Preparation of Compound 19-1

Synthesis Example 1-1 was prepared in the same manner except that Preparation Example B5 was used instead of Preparation Example A1.

Synthesis Example 19-2) Preparation of Compound 19-2

Synthesis was conducted in the same manner as in Synthesis Example 2-2.

Synthesis Example 19-3) Preparation of Compound 19

Was synthesized in the same manner as in Synthesis Example 1-3, except that the above-obtained Compounds 19-1 and 19-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 89.96; H, 6. 15; N, 3.89 HRMS [M] < ⁺ & gt ^; : 719

4.10. Preparation of Compound 20

Synthesis Example 20-1) Preparation of Compound 20-1

Synthesis was conducted in the same manner as in Synthesis Example 19-1.

Synthesis Example 20-2) Preparation of Compound 20-2

Synthesis was conducted in the same manner as in Synthesis Example 3-2.

Synthesis Example 20-3) Preparation of Compound 20

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 20-1 and 20-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.04; H, 6.40; N, 3.56 HRMS [M] < ⁺ & gt ^; : 785

4.11. Preparation of Compound 21

Synthesis Example 21-1) Preparation of Compound 21-1

Synthesis was conducted in the same manner as in Synthesis Example 19-1.

Synthesis Example 21-2) Preparation of Compound 21-2

Synthesis was conducted in the same manner as in Synthesis Example 8-2.

Synthesis Example 21-3) Preparation of Compound 21

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 21-1 and 21-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.39; H, 6.26; N, 3.35 HRMS [M] < ⁺ & gt ^; : 835

4.12. Preparation of Compound 22

Synthesis Example 22-1) Preparation of Compound 22-1

Synthesis was conducted in the same manner as in Synthesis Example 18-1.

Synthesis Example 22-2) Preparation of Compound 22-2

Synthesis was conducted in the same manner as in Synthesis Example 8-2.

Synthesis Example 22-3) Preparation of Compound 22

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the compounds 22-1 and 22-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.39; H, 6.26; N, 3.35 HRMS [M] < ⁺ & gt ^; : 835

4. 13. Example  23 manufacture

Synthesis Example 23-1) Preparation of Compound 23-1

Synthesis was conducted in the same manner as in Synthesis Example 19-1.

Synthesis Example 23-2) Preparation of Compound 23-2

Preparation Example in Synthesis Example 3-2 Preparation Example A7 instead of Compound A1 A compound 9-bromo-5- (4-tert-butylphenyl) -7,7,13,13-tetramethyl-7,13-dihydro- , 2-b] acridine was used as the starting material.

Synthesis Example 23-3) Preparation of Compound 23

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 23-1 and 23-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.15; H, 6.93; N, 2.92 HRMS [M] < ⁺ & gt ^; : 957

4.14. Preparation of Compound 24

Synthesis Example 24-1) Preparation of Compound 24-1

Synthesis was conducted in the same manner as Synthesis Example 11-1.

Synthesis Example 24-2) Preparation of Compound 24-2

Synthesis was conducted in the same manner as in Synthesis Example 12-2.

Synthesis Example 24-3) Preparation of Compound 24

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 24-1 and 24-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.04; H, 6.21; N, 3.75 HRMS [M] < ⁺ & gt ^; : 745

4.15. Preparation of Compound 25

Synthesis Example 25-1) Preparation of Compound 25-1

Synthesis was conducted in the same manner as in Synthesis Example 19-1.

Synthesis Example 25-2) Preparation of Compound 25-2

Synthesis was conducted in the same manner as in Synthesis Example 12-2.

Synthesis Example 25-3) Preparation of Compound 25

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the above-obtained Compounds 25-1 and 25-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 90.45; H, 6.31; N, 3.25 HRMS [M] < ⁺ & gt ^; : 861

4.16. Preparation of Compound 26

Synthesis Example 26-1) Preparation of Compound 26-1

Synthesis was conducted in the same manner as in Synthesis Example 19-1.

Synthesis Example 26-2) Preparation of Compound 26-2

Preparation Example 3-2-2 Preparation B2 Compound 9-bromo-5- (4-tert-butylphenyl) -7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno [1 , 2-b] acridine was used as the starting material.

Synthesis Example 26-3) Preparation of Compound 26

Synthesis was conducted in the same manner as in Synthesis Example 1-3, except that the compounds 26-1 and 26-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.75; H, 6. 18; N, 3.07 HRMS [M] < ⁺ & gt ^; : 911

4.17. Example  27 manufacture

Synthesis Example 27-1) Preparation of Compound 27-1

Synthesis was conducted in the same manner as Synthesis Example 11-1.

Synthesis Example 27-2) Preparation of Compound 27-2

Preparation Example 3-2 In the same manner as in Preparation Example 3-2 except using 2- (7-bromo-9,9-dimethyl-9H-fluoren-2-yl) -9,9-dimethyl-10-phenyl-9,10-dihydroacridine Were synthesized in the same manner.

Synthesis Example 27-3) Preparation of Compound 27

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 27-1 and 27-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.45; H, 6.31; N, 3.25 HRMS [M] < ⁺ & gt ^; : 861

4.18. Preparation of Compound 28

Synthesis Example 28-1) Preparation of Compound 28-1

Synthesis was conducted in the same manner as in Synthesis Example 19-1.

Synthesis Example 28-2) Preparation of Compound 28-2

9-dimethyl-9H-fluoren-2-yl) -10- (4-tert-butylphenyl) -9,9-dimethyl-9 , 10-dihydroacridine were used as the starting materials.

Synthesis Example 28-3) Preparation of Compound 28

Was synthesized in the same manner as in Synthesis Example 1-3, except that the compounds 28-1 and 28-2 obtained above were used instead of the compounds 1-1 and 1-2.

Elemental Analysis: C, 90.73; H, 6.69; N, 2.58 HRMS [M] < ⁺ & gt ^; : 1083

4.19. Preparation of Compound 29

Synthesis Example 29-1) Preparation of Compound 29-1

(16.5 mmol) of 9-bromo-7,7,13,13-tetramethyl-5-phenyl-7,13-dihydro-5H- indeno [1,2- b] acridine and 5.1 g of bis (pinacolato) diboron 0.36 g (3 mol%) of [1,1 bis (diphenylphosphino) ferrocene] dichloropalladium (II) and 4.8 g (3 eq.) Of potassium acetate were placed in a 250 ml round- over-night. H ₂ O was added to terminate the reaction. Then, methylene chloride was added to separate the H ₂ O layer and the organic layer. After the solvent was removed under reduced pressure, the solvent was removed by column chromatography to obtain 7,7,13,13-tetramethyl-5-phenyl-9- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- -yl) -7,13-dihydro-5H-indeno [1,2-b] acridine (yield: 76%).

Synthesis Example 29-2) Preparation of Compound 29-2

2,7-dibromo-9,9-dimethyl-9H-fluorene (7.74 g, 22.0 mmol) and diphenylamine (3.8 g, 22.6 mmol) were dissolved in 70 mL of toluene under a nitrogen atmosphere and then 0.4 g of tribenzylideneacetone dipalladium , 0.5 mmol) were placed under nitrogen. Then, P (t-Bu) 3 (0.2 g, 0.9 mmol) was added to the reaction mixture, and NaOBut (2.6 g, 27.1 mmol) was added thereto and the reaction solution was refluxed for 24 hours. After the reaction was completed, the palladium was removed by hot filtration through a thin pad of silica gel and passed through a silica gel column at a ratio of hexane to dichloromethane 7: 3. The solvent was removed and vacuum drying was conducted to obtain 8.05 g (18.5 mmol) of 7-bromo-9,9-dimethyl-N, N-diphenyl-9H-fluoren-2-amine (yield: 84%).

Synthesis Example 29-3) Preparation of Compound 29

The compound 7,7,13,13-tetramethyl-5-phenyl-9- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- (12.5 mmol) of 13-dihydro-5H-indeno [1,2-b] acridine and the compound 7,7,13,13-tetramethyl-5-phenyl- 9- , 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -7,13-dihydro-5H-indeno [1,2- b] acridine (1 equiv), tetrakis (triphenylphosphine) palladium (5 mol%) and 13 g (3 equivalents) of potassium carbonate were placed in a 250 ml round-bottom flask together with 61 ml of 1,4-dioxane and 18 ml of H ₂ O and refluxed under nitrogen for 3 hours. After completion of the reaction, the reaction mixture was subjected to column chromatography to obtain 9,9-dimethyl-N, N-diphenyl-7- (7,7,13,13-tetramethyl-5-phenyl-7,13-dihydro- (4.7 g, 5.9 mmol) (47% yield) of [1,2-b] acridin-9-yl) -9H-fluoren-

Elemental Analysis: C, 89.96; H, 6. 36; N, 3.68 HRMS [M] < ⁺ & gt ^; : 759

4.20. Preparation of Compound 30

Synthesis Example 30-1) Preparation of Compound 30-1

Bromo-7,7,13,13-tetramethyl-5-phenyl-7,13-dihydro-5H-indeno [1,2- b] acridine in Synthesis Example 29-1 instead of 9- Synthesis was carried out in the same way except that 13,13-tetramethyl-5- (naphthalen-2-yl) -7,13-dihydro-5H-indeno [1,2- b] acridine was used.

Synthesis Example 30-2) Preparation of Compound 30-2

7,7,13,13-tetramethyl-5- (naphthalen-2-yl) -9- (4,4,5,5-tetramethyl- 1,3,2-dioxaborolan- (13.2 mmol), 2,7-dibromo-9,9-dimethyl-9H-fluorene (1 eq.), and tetrakis (triphenylphosphine) palladium (5 mol%) and 15 g (3 equivalents) of potassium carbonate were placed in a 250 ml round-bottomed flask together with 61 ml of 1,4-dioxane and 18 ml of H2O, and the mixture was refluxed under nitrogen for 3 hours. After completion of the reaction, the reaction mixture was subjected to column chromatography to obtain 9- (7-bromo-9,9-dimethyl-9H-fluoren-2-yl) -7,7,13,13-tetramethyl- 5- (naphthalen- -yl) -7,13-dihydro-5H-indeno [l, 2-b] acridine as a white solid (9.7 mmol, yield 73%).

Synthesis Example 30-3) Preparation of Compound 30

Synthesis of Compound 9- (7-bromo-9,9-dimethyl-9H-fluoren-2-yl) -7,7,13,13-tetramethyl- 5- (naphthalen- (9.7 mmol) of the compound 7,7,13,13-tetramethyl-5- (naphthalen-2-yl) -7,13-dihydro-5H- -yl) -9- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -7,13-dihydro-5H- indeno [1,2- b] acridine 1.5 g (5 mol%) of tetrakis (triphenylphosphine) palladium (0) and 10 g (3 equivalents) of potassium carbonate were placed in a 250 ml round-bottomed flask with 61 ml of 1,4-dioxane and 18 ml of H ₂ O, And the mixture was refluxed and stirred. After completion of the reaction, the reaction solution was subjected to column chromatography to obtain 9- (9,9-dimethyl-7- (11,11,13,13-tetramethyl-5- (naphthalen- 5H-indeno [2,1-b] acridin-9-yl) -9H-fluoren-2-yl) -7,7,13,13-tetramethyl- 5- (naphthalen- dihydro-5H-indeno [1,2-b] acridine (yield: 68%).

Elemental Analysis: C, 91.17; H, 6. 27; N, 2.56 HRMS [M] < ⁺ & gt ^; : 1091

4.21. Preparation of Compound 31

Synthesis Example 31-1) Preparation of Compound 31-1

Preparation Example B4 was synthesized in the same manner as in the synthesis.

Synthesis Example 31-2) Preparation of Compound 31-2

Bromo-9,9-dihydro-5H-indeno [1,2-b] acridine instead of 9-bromo-7,7,13,13-tetramethyl- dimethyl-10-phenyl-9,10-dihydroacridine.

Synthesis Example 31-3) Preparation of Compound 31

9-dimethyl-9H-fluoren-2-yl) -9,9-dimethyl-10-quinolinone was obtained in the same manner as in Synthesis Example 30-3, - (naphthalen-2-yl) -9,10-dihydroacridine, the compound of Synthesis Example 31-2 was used instead of the compound of Synthesis Example 30-1, 9,9-dimethyl- -tetramethyl-1,3,2-dioxaborolan-2-yl) -9,10-dihydroacridine.

Elemental Analysis: C, 90.33; H, 6.21; N, 3.45 HRMS [M] < ⁺ & gt ^; : 809

4.22. Preparation of Compound 32

Synthesis Example 32-1) Preparation of Compound 32-1

Preparation Example B1 Synthesis was carried out in the same manner except that 2,7-dibromo-9,9-dimethyl-9H-fluorene was used instead of 1,4-dibromobenzene in the synthesis process.

Synthesis Example 32-2) Preparation of Compound 32-2

The same procedures as described in Synthesis Example 29-1 were repeated except that 9-bromo-7,7,13,13-tetramethyl-5-phenyl-7,13-dihydro-5H-indeno [ 4-bromophenyl) -7,7,13,13-tetramethyl-5-phenyl-7,13-dihydro-5H-indeno [1,2-b] acridine.

Synthesis Example 32-3) Preparation of Compound 32

9-dimethyl-9H-fluoren-2-yl) -9,9-dimethyl-10-quinolinecarboxylate instead of the compound of Synthesis Example 30-2 in Synthesis Example 30-3 phenyl-9,10-dihydroacridine was obtained in the same manner as in Synthesis Example 30-1 except that 7,7,13,13-tetramethyl-5-phenyl-9- (4- (4,4,5,5- 5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -7,13-dihydro-5H-indeno [1,2- b] acridine.

Elemental Analysis: C, 90.72; H, 6.34; N, 2.94 HRMS [M] < ⁺ & gt ^; : 951

4.23. Preparation of Compound 33

Synthesis Example 33-1) Production of Compound 33-1

Synthesis was conducted in the same manner as in Synthesis Example 32-2.

Synthesis Example 33-2) Preparation of Compound 33

Synthesis Example 30-3 Instead of the compound of Synthesis Example 30-2, 10- (4-bromophenyl) -12,12,13,13-tetramethyl-5-phenyl-12,13-dihydro-5H-indeno [2,1- a] acridine, instead of the compound of Synthesis Example 30-1, 7,7,13,13-tetramethyl-5-phenyl-9- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Synthesis was carried out in the same manner, except that 2-yl) phenyl) -7,13-dihydro-5H-indeno [1,2-b] acridine was used.

Elemental Analysis: C, 90.72; H, 6.34; N, 2.94 HRMS [M] < ⁺ & gt ^; : 951

4.24. Preparation of Compound 34

Synthesis Example 34-1) Preparation of Compound 34-1

Synthesis was carried out in the same manner as in Synthesis Example 1-1.

Synthesis Example 34-2) Preparation of Compound 34-2

Synthesis Example 11-2 was synthesized in the same manner except that 3,6-dibromo-9H-carbazole was used instead of 1,4-dibromobenzene.

Synthesis Example 34-3) Preparation of Compound 34

Except for using the compounds 34-1 and 34-2 obtained above in place of the compounds 1-1 and 1-2 in Synthesis Example 1-3.

Elemental Analysis: C, 87.82; H, 5.64; N, 6.54 HRMS [M] < ⁺ & gt ^; : 641

4.25. Preparation of Compound 35

Synthesis Example 35-1) Production of Compound 35-1

Synthesis was conducted in the same manner as in Synthesis Example 5-1.

Synthesis Example 35-2) Preparation of Compound 35-2

Synthesis Example 11-2 was synthesized in the same manner except that 5,5'-dibromo-2,2'-bipyridine was used instead of 1,4-dibromobenzene.

Synthesis Example 35-3) Preparation of Compound 35

Was synthesized in the same manner as in Synthesis Example 1-3, except that the above-obtained Compounds 35-1 and 35-2 were used instead of Compounds 1-1 and 1-2.

Elemental Analysis: C, 86.53; H, 6.51; N, 6.96 HRMS [M] < ⁺ & gt ^; : 803

Preparation of [Examples 1] to [Example 35]

Preparation and evaluation of organic EL device

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was cleaned with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum evaporator.

A blue organic electroluminescent device including the compound of the present invention as a dopant was prepared on the ITO (anode) prepared as described above. The structure of the device is shown in Table 1 below.

HL HTL EML ETL EIL Cathode Materials DS-205 NPB Host-Dopant Alq3 LiF Al Thickness / Å 600 150 285 + 15 250 10 2,000 Evapo.temp / ℃ 360 to 370 230-240 Host: 240 ~ 250
Dopant: 170-180 240-250 - -

The hole injection layer (HIL) used was DS-205 (arylamine derivative) of Doosan Corp. to a thickness of 600 Å and NPL (see Formula 5 below) to a thickness of 150 Å for a hole transport layer (HTL). AND (see Chemical Formula 6 below) was used as a host, and the compounds of the above synthesis examples were used as dopants, respectively. The doping amount of the dopant was 5%, the electron transport layer (ETL) Alq3 (see Chemical Formula 7) was formed to a thickness of 250 Å, and the electron injection layer (EIL) .

[Chemical Formula 5]

[Formula 6]

[Formula 7]

[Formula 8]

Comparative Example 1

And the organic foot was evaluated in the same manner as in Example 34, except that the following BD-1 (see Chemical Formula 9) was used as a dopant of the light emitting layer.

[ Chemical Formula 9]

[Experimental Example]

Luminous Characteristic Evaluation

The luminescent characteristics of the organic luminescent compound according to the present invention prepared in Examples 1 to 35 and the OLED device containing the conventional luminescent compound (Comparative Example) were evaluated at a current density of 10 mA / cm 2. The results are shown in Table 2.

division compound Voltage (V) Pl peak
(nm) Efficiency (cd / A) Example 1 One 3.9 451 6.6 Example 2 2 4.1 451 6.3 Example 3 3 4.0 453 6.2 Example 4 4 4.2 454 6.4 Example 5 5 4.2 439 6.8 Example 6 6 4.0 440 6.8 Example 7 7 3.7 453 6.4 Example 8 8 4.0 453 6.5 Example 9 9 4.0 452 6.9 Example 10 10 3.9 458 6.8 Example 11 11 3.8 459 6.4 Example 12 12 3.7 450 6.8 Example 13 13 3.7 440 6.3 Example 14 14 3.7 448 6.7 Example 15 15 3.9 463 6.4 Example 16 16 3.5 452 6.7 Example 17 17 3.8 451 6.6 Example 18 18 3.8 457 6.7 Example 19 19 3.8 462 6.5 Example 20 20 3.7 451 6.9 Example 21 21 3.5 449 6.8 Example 22 22 3.5 441 6.2 Example 23 23 3.8 443 6.4 Example 24 24 3.8 461 5.9 Example 25 25 3.7 453 5.8 Example 26 26 3.9 452 6.4 Example 27 27 3.9 452 6.5 Example 28 28 4.0 453 6.7 Example 29 29 4.0 458 6.4 Example 30 30 4.2 457 6.3 Example 31 31 4.1 461 6.5 Example 32 32 4.1 451 6.5 Example 33 33 4.2 449 6.3 Example 34 34 4.6 459 5.9 Example 35 35 4.6 455 5.8 Comparative example BD-1 4.7 458 5.6

As described above, the novel compound containing an acridine structure of the present invention and the organic electroluminescent device using the same can synthesize a thermally stable novel styryl compound represented by the general formula (1) The use of the organic electroluminescent layer as a dopant of the organic light emitting layer (EML) of the light emitting device can provide a blue organic electroluminescent device having a low driving voltage, improved luminous efficiency, prolonged service life, and excellent thermal stability.

While the present invention has been particularly shown and described with reference to specific embodiments thereof, those skilled in the art will appreciate that such specific embodiments are merely preferred embodiments and that the scope of the present invention is not limited thereby. something to do. It is therefore intended that the scope of the invention be defined by the claims appended hereto and their equivalents.

100: organic electroluminescent device 101: substrate
102: Positive electrode 103: Hole injection layer
104: Hole transport layer 105: Light emitting layer
106: hole blocking layer 107: electron transporting layer
108: electron injection layer 109: cathode

Claims (7)

A compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
A and B are each independently selected from a single bond, a substituted or an aryl group of a beach C ₆ ~ C ₆₀ ring, and a substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group consisting of a ring;
n is 0 or 1, except when A and B are single bonds when n is 0;
Ar ₁ and Ar ₂ are each independently selected from the group consisting of Formula 2 to Formula 4, except that Ar ₁ and Ar ₂ are simultaneously Formula 4;
(2)

(3)

[Chemical Formula 4]

Each of R ₁ to R ₁₀ independently represents a substituted or unsubstituted C ₁ to C ₆₀ alkyl group, a substituted or unsubstituted C ₂ to C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ to C ₆₀ alkynyl group, A substituted or unsubstituted C ₆ to C ₆₀ aryl group, a substituted or unsubstituted C ₃ to C ₆₀ heteroaryl group, a substituted or unsubstituted C ₁ to C ₆₀ alkoxy group, a substituted or unsubstituted C ₆ to C ₆₀ aryl group, ~ C ₆₀ of the aryloxy group, a substituted or unsubstituted C ₇ ~ C ₆₀ aryl group, a substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group, a substituted or unsubstituted C ₃ ~ cycloalkyl group of C ₆₀ of the , A substituted or unsubstituted C ₁ to C ₆₀ halogenalkyl group, a substituted or unsubstituted C ₁ to C ₆₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ alkylsilyl group, a substituted or unsubstituted A C ₃ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₁ to C ₆₀ heteroarylsilyl group;
R ₁ to R ₈ may each be fused or may form a ring with adjacent substituents;
X ₁ to X ₅ are each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, substituted or unsubstituted C ₁ ~ C ₆₀ alkyl group, substituted or unsubstituted C ₂ ~ C ₆₀ alkenyl group, Substituted or unsubstituted C ₂ ~ C ₆₀ alkynyl group, substituted or unsubstituted C ₆ ~ C ₆₀ aryl group, substituted or unsubstituted C ₃ ~ C ₆₀ heteroaryl group, substituted or unsubstituted C ₁ An alkoxy group of -C ₆₀ , a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ alkylamino group, a substituted or unsubstituted C ₆ -C ₆₀ arylamino group, Substituted or unsubstituted C ₆ -C ₆₀ diarylamino group, substituted or unsubstituted C ₃ -C ₆₀ heteroarylamino group, substituted or unsubstituted C ₂ -C ₆₀ diheteroarylamino group, substituted or unsubstituted C ₇ -C ₆₀ arylalkyl group, substituted or unsubstituted C ₃ -C ₆₀ heteroarylalkyl group, substituted or unsubstituted C ₃ -C ₆₀ A substituted or unsubstituted C ₁ to C ₆₀ halogenoalkyl group, a substituted or unsubstituted C ₁ to C ₆₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ to C ₆₀ alkylsilyl group, a substituted or unsubstituted C ₁ to C ₆₀ alkyl group, A substituted C ₃ to C ₆₀ arylsilyl group, and a substituted or unsubstituted C ₁ to C ₆₀ heteroarylsilyl group;
p, q, r, s and t are each independently an integer of 0 to 4;
The method of claim 1,
At least one of Ar ₁ and Ar ₂ is a compound characterized in that the formula (2a).
(2a)

The method of claim 1,
At least one of Ar ₁ and Ar ₂ is a compound characterized in that the formula (3a) or formula (3b).
[Chemical Formula 3]

(3b)

The method of claim 1,
The substituted or unsubstituted C ₆ to C ₆₀ aryl group and the substituted or unsubstituted C ₃ to C ₆₀ heteroaryl group selected from A and B are each independently substituted or unsubstituted phenyl, substituted or unsubstituted. Substituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyri Chopped, substituted or unsubstituted pyrazine, substituted or unsubstituted triazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted carbazole, and substituted or unsubstituted ring is selected from the group consisting of a trawl phenanthryl Lin, each substituent used in the substituted screen, characterized in that the alkyl group of C ₁ ~ C ₅ alkyl group substituted with a halogen atom or an unsubstituted C ₁ ~ C ₅ Water.
The method of claim 1,
The R ₁ , R ₄ , R ₉ And substituted is selected as R _10, or unsubstituted C ₆ ~ C ₆₀ aryl group, and a group heteroaryl substituted or unsubstituted C ₃ ~ C _60, each independently represent a substituted or unsubstituted phenyl, substituted or unsubstituted ring Biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted Substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrazine, Substituted or unsubstituted isoquinolines, and substituted or unsubstituted carbazoles, and each of the substituents used for the substitution is selected from the group consisting of a C ₁ to C ₅ alkyl group or a C ₁ to C ₅ substituted egg Compound, characterized in that group.
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 organic layers is at least one of claims 1 to 5 An organic electroluminescent device comprising the compound according to any one of claims.
The method according to claim 6,
Wherein the organic material layer is a light emitting layer.

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