KR20140029182A - Organic light compound and organic light device using the same - Google Patents

Abstract

The present invention relates to an organic light-emitting compound and an organic light-emitting device using the same, and more particularly, to: an organic light-emitting device capable of realizing excellent luminous efficiency, brightness, and light-emitting life and an organic light-emitting compound used for the same; or an optical device for solar power generation and an optical compound used for the same. In particular, by developing an indazole-based compound and an organic light-emitting device using the same, a material can be developed, which can be variously used for diverse organic films, for example, an electron transport layer (ETM), an emission layer (EML), a hole transporting layer (HTM), a hole injection layer (HIL) and the like between a first and a second electrode and can provide the performance improvement such as efficiency enhancement and operational voltage reduction as well as the maximization of ability as an OLED material.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound, and an organic electroluminescent device using the electroluminescent compound.

The present invention relates to an organic light emitting compound and an organic light emitting device using the same.

The most important factor determining the luminous efficiency in an OLED is a light emitting material. Fluorescent materials are widely used as luminescent materials to date, but the development of a phosphorescent material on the mechanism of electroluminescence is one of the best ways to improve the luminous efficiency up to 4 times theoretically. Until now, iridium (III) complexes have been widely known as phosphorescent materials. Materials such as (acac) Ir (btp) ₂ , Ir (ppy) ₃ and Firpic are known for each RGB. Recently, many phosphorescent materials have been studied in Japan and Europe.

4,4'-N, N'-dicarbazole-biphenyl (CBP) has been widely known as a host material for phosphorescent emitters, and a high-efficiency organic EL device using a hole blocking layer such as a phenanthroline derivative (BCP) Of OLEDs are known. In Japan, Pioneer and the like, a high-performance OLED using a BAlq derivative as a host is known.

In addition, although the electron transporting materials disclosed in JP-A-11-345686 contain an oxazole group and a thiazole group and can also be applied to a light emitting layer, they have come to practical use in terms of driving voltage, luminance, I can not.

However, existing materials have advantages in terms of luminescent properties, but they have disadvantages such as low glass transition temperature and very poor thermal stability, which can cause material changes when subjected to a high temperature deposition process under vacuum. Because OLEDs have power efficiency = (π / voltage) ㅧ current efficiency, the power efficiency is inversely proportional to the voltage. OLEDs using real phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials. However, when conventional materials such as BAlq and CBP are used as hosts for phosphorescent materials, OLEDs using fluorescent materials (Lm / w) because the driving voltage is higher than that of the conventional device. In addition, since the lifetime of the OLED device is never satisfactory, development of a more stable and more excellent host material is required.

The first technical problem to be solved by the present invention is to provide a novel indazole-based organic light emitting compound that can be applied to an organic optical device, in particular an organic light emitting device.

The second technical problem to be solved by the present invention is to provide an organic light emitting device, including the novel indazole-based organic light emitting compound, low driving voltage, improved luminous efficiency, brightness, thermal stability and lifespan.

The present invention is characterized by an indazole type organic light emitting compound represented by the following formula (F1) or formula (F2).

[Formula F1]

[Formula F2]

In Chemical Formula F1 or F2,

R ₁ , R ₂ , R ₃ , and R ₄ , which are the same as or different from each other, represent a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₅ -C ₄₀ aryl group, or a C ₅ -C ₄₀ heteroaryl group, or R ₁ , R ₂ , R ₃ , and R ₄ may combine two adjacent groups to form a fused C _{5 to} C ₄₀ aryl group;

A ₁ and A ₂ , which are the same or different, represent N or CR ₅ , wherein R ₅ represents a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₅ -C ₄₀ aryl group, or a C ₅ -C ₄₀ heteroaryl group ;

X ₁ and X ₂ , which are the same as or different from each other, represent a single bond, S, O, CR ^a R ^b , SiR ^a R ^b , or N- (L ₃ ) _m -L ₄ ;

L ₁ and L ₃ , which are the same as or different from each other, represent a C ₃ to C ₄₀ cycloalkyl group, or a C _{5 to} C ₄₀ aryl group;

L ₂ and L _4, the same as or different from each other, represent a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₃ -C ₄₀ heterocycloalkyl group, or a C ₅ -C ₄₀ heteroaryl group;

R ^a and R ^b are the same as or different from each other and are a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{3 to} C ₄₀ cycloalkyl group, a C _{3 to} C ₄₀ heterocycloalkyl group, or C ₅ It represents a ~C ₄₀ heteroaryl;

m is 0 or 1;

In addition, the heterocycloalkyl or heteroaryl used in the definition of the substituents A ₁ , A ₂ , L ₂ , L ₄ , R ^a , and R ^b may include 1 to 4 heteroatoms selected from O, S, N, and Si. Can,

Also used in the definitions of the substituents R ₁ , R ₂ , R ₃ , R ₄ , A ₁ , A ₂ , L ₁ , L ₂ , L ₃ , L ₄ , R ^a , and R ^b , cycloalkyl, hetero Aryl, or heterocycloalkyl, may be monocyclic or consist of 2 to 7 polycyclic, which monocyclic or polycyclic is deuterium, C ₁ -C ₄₀ alkyl, C ₃ -C ₄₀ cyclo Selected from the group consisting of alkyl, C ₅ -C ₄₀ arylamino, di (C ₅ -C ₄₀ aryl) amino, C ₅ -C ₄₀ aryl, C ₃ -C ₄₀ heterocycloalkyl, and C ₅ -C ₄₀ heteroaryl Aryl or heteroaryl, which may be substituted or unsubstituted with a substituent, and defined as a substituent of the above monocyclic or polycyclic ring, may be substituted with C ₁ -C ₄₀ alkyl, C ₅ -C ₄₀ aryl, and C ₅ -C ₄₀ heteroaryl. It may be substituted or unsubstituted again with a substituent selected from the group consisting of.

In addition, the present invention is a first electrode; A second electrode; And an organic light emitting device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film includes an indazole-based organic light emitting compound represented by Formula F1 or Formula F2. It is done.

The organic light emitting device including the indazole-based organic light emitting compound according to the present invention can realize high luminous efficiency, high luminous luminance, and significantly improved luminous lifetime.

Accordingly, the present invention provides a novel organic light emitting compound and an organic light emitting device comprising the compound.

Hereinafter, the present invention will be described in more detail.

While the present invention has been described in connection with what is presently considered to be the most practical and preferred embodiment, it is to be understood that the invention is not limited to the disclosed embodiments. It is to be understood, however, that the invention is not intended to be limited to the particular forms disclosed, but on the contrary, is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms " comprises, " or " comprising " and the like are used to specify that a feature, a number, a step, an operation, an element, a part, But do not preclude the presence or addition of one or more other features, numbers, steps, operations, components, parts, or combinations thereof.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.

Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.

The present invention is to develop an organic light emitting compound, in particular indazole-based compound, various organic membranes between the first electrode and the second electrode such as electron transport layer (ETM), light emitting layer (EML), hole transport layer (HTM), hole injection layer (HIL) We propose materials that can be used in various ways, and improve materials such as increasing efficiency and decreasing driving voltage, and develop materials that maximize their ability as OLED materials.

In the present specification, the organic luminescent compound means a compound used in an organic photonic device, and is not necessarily limited in its range of application, and its application range is not limited to the organic luminescent layer but may be an organic luminescent layer such as a charge injection layer and a charge transport layer Can be used for any layer constituting the substrate.

In this specification, the terms 'light emitting compound' and 'light emitting device' are used to cover the case where the present invention is applied to both an organic light emitting device and a device for solar power generation regardless of a dictionary or customary definition It is a selected term.

An organic photonic device according to a first aspect of the present invention includes: a first electrode; A second electrode; And an organic optical device including at least one organic film between the first electrode and the second electrode, wherein the organic film includes an organic light emitting compound represented by Formula F1 or Formula F2.

[Formula F1]

[Formula F2]

In Chemical Formula F1 or F2,

R ₁ , R ₂ , R ₃ , and R ₄ , which are the same as or different from each other, represent a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₅ -C ₄₀ aryl group, or a C ₅ -C ₄₀ heteroaryl group, or R ₁ , R ₂ , R ₃ , and R ₄ may combine two adjacent groups to form a fused C _{5 to} C ₄₀ aryl group;

A ₁ and A ₂ , which are the same or different, represent N or CR ₅ , wherein R ₅ represents a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₅ -C ₄₀ aryl group, or a C ₅ -C ₄₀ heteroaryl group ;

X ₁ and X ₂ , which are the same as or different from each other, represent a single bond, S, O, CR ^a R ^b , SiR ^a R ^b , or N- (L ₃ ) _m -L ₄ ;

L ₁ and L ₃ , which are the same as or different from each other, represent a C ₃ to C ₄₀ cycloalkyl group, or a C _{5 to} C ₄₀ aryl group;

L ₂ and L _4, the same as or different from each other, represent a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₃ -C ₄₀ heterocycloalkyl group, or a C ₅ -C ₄₀ heteroaryl group;

R ^a and R ^b are the same as or different from each other and are a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{3 to} C ₄₀ cycloalkyl group, a C _{3 to} C ₄₀ heterocycloalkyl group, or C ₅ It represents a ~C ₄₀ heteroaryl;

m is 0 or 1;

In addition, the heterocycloalkyl or heteroaryl used in the definition of the substituents A ₁ , A ₂ , L ₂ , L ₄ , R ^a , and R ^b may include 1 to 4 heteroatoms selected from O, S, N, and Si. Can,

Also used in the definitions of the substituents R ₁ , R ₂ , R ₃ , R ₄ , A ₁ , A ₂ , L ₁ , L ₂ , L ₃ , L ₄ , R ^a , and R ^b , cycloalkyl, hetero Aryl, or heterocycloalkyl, may be monocyclic or consist of 2 to 7 polycyclic, which monocyclic or polycyclic is deuterium, C ₁ -C ₄₀ alkyl, C ₃ -C ₄₀ cyclo Selected from the group consisting of alkyl, C ₅ -C ₄₀ arylamino, di (C ₅ -C ₄₀ aryl) amino, C ₅ -C ₄₀ aryl, C ₃ -C ₄₀ heterocycloalkyl, and C ₅ -C ₄₀ heteroaryl Aryl or heteroaryl, which may be substituted or unsubstituted with a substituent, and defined as a substituent of the above monocyclic or polycyclic ring, may be substituted with C ₁ -C ₄₀ alkyl, C ₅ -C ₄₀ aryl, and C ₅ -C ₄₀ heteroaryl. It may be substituted or unsubstituted again with a substituent selected from the group consisting of.

The inventors of the present invention as a substituent of the organic light emitting compound represented by Formula F1 or Formula F2 R ₁ , R ₂ , R ₃ , R ₄ , A ₁ , A ₂ , X ₁ , X ₂ , L ₁ , and L ₃ By developing various specific derivatives, an organic photochemical compound which can be used as various organic films between the first electrode and the second electrode, such as an electron transport layer (ETM), an emission layer (EML), a hole transport layer (HTM), etc. When developing an optical device and using it as an organic light emitting device, it has been found that it is possible to maximize performance as an OLED material and to improve performance, such as increased efficiency and a decrease in driving voltage, and in particular, light emission life is remarkably improved. It is expected that excellent power generation efficiency can be obtained when applied to the field of optical device and optical compound.

Hereinafter, the organic light emitting compound represented by Chemical Formula F1 or Chemical Formula F2 will be described with reference to the organic light emitting device, but the present invention should not be construed as a limitation.

The organic light emitting compound represented by Chemical Formula F1 or Chemical Formula F2 is suitable as a material forming an organic film interposed between the first electrode and the second electrode among organic optical devices. The organic light emitting compound represented by Chemical Formula F1 or Chemical Formula F2 is suitable for use in an organic film, particularly a hole transport layer, a hole injection layer, an electron transport layer, or a light emitting layer of an organic light emitting device, and is used as a dopant material as well as a host material. The organic light emitting compound represented by Chemical Formula F1 or Chemical Formula F2 provides a green color and is suitable for use in a light emitting device such as white.

Specific examples of the substituent of the organic light emitting compound represented by Formula F1 or Formula F2 are as follows.

R ₁ , R ₂ , R ₃ , and R ₄ are the same as or different from each other and are a hydrogen atom, a C ₁ -C ₁₀ alkyl group, a phenyl group, a naphthalenyl group, a pyridyl group, a pyrimidyl group, or a triazinyl group, or R ₁ , R ₂ , R ₃ , and R ₄ may combine two adjacent groups to form a fused phenyl group or a fised naphthalenyl group.

The A ₁ and A ₂ are the same as or different from each other and represent N or CR ₅ , wherein R ₅ may represent a hydrogen atom, a C _{1 to} C ₁₀ alkyl group, or a phenyl group.

X ₁ and X ₂ are the same as or different from each other, and a single bond, S, O, CH (C ₁ -C ₁₀ alkyl), C (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl), CH (C _5- C ₁₀ aryl), C (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl), SiH (C ₁ -C ₁₀ alkyl), Si (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ Alkyl), SiH (C ₅ -C ₁₀ aryl), Si (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl) or N- (L ₃ ) _m -L ₄ .

,나프탈레닐렌기, 나프탈레닐렌나프탈레닐렌기, 안트라세닐렌기, 페난트레닐렌기, 플루오레닐렌기, 또는

를 나타내고, 또한, 이들은 각각 중수소, C₁∼C₁₀알킬, 페닐, C₁∼C₁₀알킬 치환된 페닐, 바이페닐, 및 피리딜 중에서 선택된 치환체로 치환 또는 비치환될 수 있다. L ₁ and L ₃ are the same as or different from each other, a phenylene group, a biphenylene group,

Naphthalenylene group, naphthalenylene naphthalenylene group, anthracenylene group, phenanthrenylene group, fluorenylene group, or

In addition, they may be substituted or unsubstituted with a substituent selected from deuterium, C ₁ -C ₁₀ alkyl, phenyl, C ₁ -C ₁₀ alkyl substituted phenyl, biphenyl, and pyridyl, respectively.

Q ₁ is O, S, C (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl), C (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl), Si (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl) or Si (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl).

,

,

또는

를 나타내고, 또한 이들은 각각 중수소, C₁∼C₁₀알킬, 페닐, 중수소 치환된 페닐, C₁∼C₁₀알킬 치환된 페닐, 바이페닐, 나프탈레닐, 및 피리딜 중에서 선택된 치환체로 치환 또는 비치환될 수 있다.L ₂ and L ₄ represent a hydrogen atom, a C ₁ -C ₁₀ alkyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolinyl group, a quinazolinyl group, an indole group, a phenanthridine group, a benzothiazole group,

,

,

or

And are also unsubstituted or substituted with substituents selected from deuterium, C ₁ -C ₁₀ alkyl, phenyl, deuterium substituted phenyl, C ₁ -C ₁₀ alkyl substituted phenyl, biphenyl, naphthalenyl, and pyridyl, respectively. Can be.

Q ₂ , Q ₃ , and Q ₄ are the same as or different from each other and are O, S, NH, N (C ₁ -C ₁₀ alkyl), N (C ₅ -C ₁₀ aryl), C (C ₁ -C ₁₀ alkyl ) (C ₁ -C ₁₀ alkyl), C (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl), Si (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl) or Si (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl).

R ^c and R ^d are the same as or different from each other, and are C ₁ -C ₄₀ alkyl groups, C ₅ -C ₄₀ aryl groups, C ₃ -C ₄₀ cycloalkyl groups, C ₃ -C ₄₀ heterocycloalkyl groups, or C ₅ -C ₄₀ is 1 to 5 substituents selected from the heteroaryl group, and each of which is heavy hydrogen, C ₁ ~C ₁₀ alkyl, C ₅ ~C ₁₀ aryl, C ₃ ~C ₁₀ cycloalkyl, C ₃ ~C ₁₀ heterocycloalkyl, or It may be substituted or unsubstituted with 1 to 5 substituents selected from C _{5 to} C ₁₀ heteroaryl.

M denotes the number of L ₁ , and when m = 0, L ₁ does not exist, and when m = 0, L ₁ is present.

In more detail, in accordance with an embodiment of the present invention, the organic light emitting compound used in the organic light emitting device of the present invention has an indazole as a basic skeleton, specifically, as shown in the following [First Table Group] Compounds 1 to 360 may be included, but the invention is not limited thereto:

[First group (group)]

The organic light emitting compound represented by Chemical Formula F1 or Chemical Formula F2 according to the present invention may be synthesized using a conventional synthetic method, and more detailed synthetic routes of the compound may be referred to Synthesis Examples 1 to 4 below.

The organic light emitting compound represented by Chemical Formula F1 or Chemical Formula F2 is suitable for use in an organic film of an organic optical device, in particular, a hole transport layer, a hole injection layer, an electron transport layer, or a light emitting layer. The structure of the organic light emitting device according to the present invention is very diverse. The organic EL device may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron blocking layer, an electron transporting layer, and an electron injecting layer between the first electrode and the second electrode.

More specifically, the present invention provides an organic electroluminescent device, wherein the organic electroluminescent device comprises: a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes at least one organic light emitting compound selected from Formula F1 or Formula F2.

The organic electroluminescent device according to the present invention may include at least one compound represented by Formula F1 or Formula F2, and may further include a conventional host material, a common dopant material, or a mixture thereof.

The organic electroluminescent device according to the present invention includes the organic material layer as a light emitting layer, and the light emitting layer includes at least one phosphorescent dopant using at least one organic light emitting compound selected from compounds represented by Formula F1 or Formula F2 as a light emitting host. The light emitting dopant is not particularly limited.

In the organic electroluminescent device of the present invention, at least one organic light emitting compound selected from the compound represented by the formula (F1) or formula (F2), at the same time selected from the group consisting of arylamine compound or styrylarylamine compound It may further comprise a compound.

Further, in the organic light emitting device of the present invention, in addition to at least one organic light emitting compound selected from the compound represented by the formula (F1) or (F2) in the organic layer, Group 1, Group 2, 4 cycle, 5 cycle transition metal, lanthanum series metal and It may further include one or more metals or complex compounds selected from the group consisting of organic metal of the d-transition element, the organic material layer may include a light emitting layer and a charge generating layer.

In addition, an organic electroluminescent device emitting white light by simultaneously including at least one common organic light emitting layer emitting blue, red or green light in addition to the organic light emitting compound may be formed in the organic material layer.

More specifically, in an embodiment of the organic light emitting device according to the present invention, the organic light emitting device may have a structure including a first electrode / a hole injection layer / a light emitting layer / an electron transport layer / an electron injection layer / The organic light emitting device may have a structure including a first electrode / a hole injection layer / a hole transporting layer / a light emitting layer / an electron transporting layer / an electron injecting layer / a second electrode. Further, the organic light emitting device may include a first electrode / a hole injecting layer / / Light emitting layer / hole blocking layer / electron transporting layer / electron injecting layer / second electrode.

At this time, one or more of the electron transporting layer, the light emitting layer, the hole injecting layer, or the hole transporting layer may include an organic light emitting compound according to the present invention.

The light emitting layer of the organic light emitting device according to the present invention may include a phosphorescent or fluorescent dopant including red, green, blue or white. The phosphorescent dopant may be an organometallic compound containing at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb and Tm. In addition, the compound according to the present invention can also be used as a fluorescent dopant in the light emitting layer.

Hereinafter, a method of manufacturing an organic light emitting device according to the present invention will be described in detail. First, a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Here, the substrate used in a typical organic optical device is preferably a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) or the like is used which is transparent and excellent in conductivity.

Next, a hole injection layer (HIL) may be formed on the first electrode by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method.

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal characteristics of the desired hole injection layer, and the like. In general, A degree of vacuum of 10 < ^-5 > to 10 < ^-3 > torr, a deposition rate of 0.01 to 100 ANGSTROM / sec, and a film thickness of 100 ANGSTROM to 1 mu m.

When the hole injecting layer is formed by spin coating, the coating conditions vary depending on the compound used as the material of the hole injecting layer, the structure and the thermal properties of the desired hole injecting layer, and preferably from about 2000 rpm to 5000 rpm The coating speed and the heat treatment temperature for removing the solvent after coating are preferably selected in a temperature range of about 80 to 200 캜.

The hole injection layer material may be an organic light emitting compound represented by Chemical Formula F1 or Chemical Formula F2 as described above.

Alternatively, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or starburst amine derivatives such as TCTA, m-MTDATA, and m-MTDATA described in Advanced Material, 6, p.677 (1994) (2-TNATA), polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), which is a soluble conductive polymer, (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA) or polyaniline / poly (4-styrenesulfonate) (PANI / PSS ), And the like can be used.

The thickness of the hole injection layer may be about 100 A to about 10000 A, and preferably about 100 A to about 1000 A. When the thickness of the hole injection layer is less than 100 ANGSTROM, hole injection characteristics may be degraded. If the thickness of the hole injection layer is more than 10000 ANGSTROM, the driving voltage may increase.

Alternatively, the hole injection layer may be formed by a vacuum vapor deposition method. The specific deposition conditions vary depending on the compound used, but are selected from substantially the same range of conditions as the formation of a general hole injection layer. For example, N, N-bis- [4- (di-methtolylamino) phenyl] -N, N-biphenyl-4,4-diamine (DNTPD) and the like can be used.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by various methods such as a vacuum deposition method, a spin coating method, a casting method, and an LB method. In the case of forming the hole transporting layer by the vacuum deposition method and the sputtering method, the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

The hole transport layer material may include an organic light emitting compound represented by Chemical Formula F1 or Chemical Formula F2 as described above. Examples of known hole transporting materials include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'- 1-biphenyl] -4,4'-diamine (TPD), and N, N'-di A typical amine derivative, and the like. The thickness of the hole transporting layer may be about 50 A to 1000 A, preferably 100 A to 600 A. When the thickness of the hole transporting layer is less than 50 ANGSTROM, the hole transporting property may be deteriorated. When the thickness of the HTL is more than 1000 ANGSTROM, the driving voltage may increase.

Next, a light emitting layer (EML) may be formed on the hole transporting layer by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. When a light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions vary depending on the compound used, but generally, the conditions are substantially the same as those for forming the hole injection layer.

As described above, the emission layer may include a compound represented by Formula F1 or Formula F2 according to the present invention. In this case, the compound represented by Formula F1 or Formula F2 may be used with a suitable known host material or may be used with a known dopant material. It is also possible to use the compound represented by the said Formula (F1) or Formula (F2) independently.

As a host material which can be used in combination with the compound represented by the said Formula (F1) or (F2), for example, tris (8-hydroxy quinolate aluminum (Alq3), 4,4'-N, N'- dicarbazole- Biphenyl (CBP), poly (n-vinylcarbazole) (PVK), etc. In addition, as a host material, an asymmetric anthracene derivative represented by the following general formula (i), an asymmetric monoanthracene derivative represented by the following general formula (ii) , Asymmetric pyrene derivatives represented by the following formula (VII), asymmetric anthracene derivatives represented by the following formula (VII), anthracene derivatives represented by the following formula (V), anthracene derivatives represented by the following formula (VII), and spirofluorene derivatives represented by the following formula (VII) , A condensed ring-containing compound represented by the following formula (VII), a fluorene compound represented by the following formula (VII), anthracene represented by the following formula (x) It may be selected from a compound having a central skeleton, or a compound having an anthracene central skeleton represented by the following formula (xi) in which A ₁ and A ₂ are substituted with different groups in the formula (x).

(I)

(In Formula (I), Ar is a substituted or unsubstituted C _10- C ₅₀ condensed aryl group; Ar 'is a substituted or unsubstituted C ₆ -C ₅₀ aryl group; X is a substituted or unsubstituted C of ₆ ~C ₅₀ aryl group, a substituted or beach heteroaryl group can unsubstituted 5 to 50 nuclear atoms, a substituted or unsubstituted alkyl group of unsubstituted C ₁ ~C _50, substituted or unsubstituted C ₁ ~C ₅₀ alkoxy group , Substituted or unsubstituted C ₆ -C ₅₀ aralkyl group, substituted or unsubstituted aryloxy group having 6 to 50 nuclear atoms, substituted or unsubstituted arylthio group having 6 to 50 nuclear atoms, substituted or unsubstituted Ring C ₁ -C ₅₀ alkoxycarbonyl group, carboxyl group, halogen atom, cyano group, nitro group, or hydroxyl group, a, b and c are each independently an integer of 0 to 4; n Is an integer from 1 to 3, and in n may be the same or different when n is 2 or 3)

(Ii)

(In Formula (ii), Ar ¹ and Ar ² are each independently a substituted or unsubstituted C ₆ -C ₅₀ aryl group; m and n are each an integer of 1 to 4, provided that m = n = 1 and Ar Ar ¹ and Ar ² are not the same when the bond position of ¹ and Ar ^{2 to} the benzene ring is symmetric, and m and n are different integers when m or n is an integer of 2 to 4; R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or unsubstituted A substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkoxy group group, a substituted or unsubstituted substituted C ₆ ~C ₅₀ aralkyl group, the ring or unsubstituted 5 to 50 nuclear atoms aryloxy, substituted or unsubstituted nuclear atoms of 6 to 50 Im coming aryl, a substituted or unsubstituted C ₁ ~C ₅₀ alkoxy carbonyl group, a substituted or unsubstituted group in between a silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro, or hydroxyl group.)

(Iii)

[In Formula (VII), Ar and Ar 'are each independently a substituted or unsubstituted aryl group of nuclear C ₆ -C ₅₀ ; L and L 'are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalenylene group, a substituted or unsubstituted fluorenylene group or a substituted or unsubstituted dibenzylphenylene group; m is an integer from 0 to 2; n is an integer from 1 to 4; s is an integer from 0 to 2; t is an integer from 0 to 4; And L or Ar is bonded to any one of the C1 to C5 positions of the pyrene and L 'or Ar' is bonded to any one of the C6 to C10 positions of the pyrene,

Provided that Ar, Ar ', L and L' satisfy the following (1) or (2) when n + t is an even number:

(1) Ar ≠ Ar 'and / or L ≠ L' (wherein ≠ represents a group of different structure)

(2) when Ar = Ar 'and L = L'

(2-1) m? S and / or n? T, or

(2-2) When m = s and n = t,

(2-2-1) L and L ', or pyrene is bonded to other bonding sites on Ar and Ar'

(2-2-2) When L and L 'or pyrene are bonded at the same binding position on Ar and Ar', respectively, the substitution position in the pyrene of L and L 'or Ar and Ar' is C1 and C6. Position or C2 and C7 position.]

[Chemical Formula (iv)

(In Formula (X), A ¹ and A ² are each independently a substituted or unsubstituted C ₁₀ to C _{2 0} condensed aryl group; Ar ¹ and Ar ² are each independently a hydrogen atom or a substituted or unsubstituted C _6.) aryl groups and ~C ^{_50; R 1, R 2, R} 3, R 4, R 5, R 6, R 7, R 8, R 9 and R ¹⁰ is a ring C each independently represent a hydrogen atom, a substituted or unsubstituted of ₆ ~C ₅₀ aryl group, a substituted or unsubstituted heteroaryl groups in the number of nuclear atoms of 5 to 50 ring, an alkyl group a substituted or unsubstituted C ₁ ~C _50, a substituted or unsubstituted C ₃ ~C ₅₀ cycloalkyl group , Substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C ₆ -C ₅₀ aralkyl group, substituted or unsubstituted aryloxy group having 6 to 50 nuclear atoms, substituted or unsubstituted Arylthio groups having 6 to 50 nuclear atoms, substituted or unsubstituted C ₁ to C ₅₀ alkoxycarbonyl groups, substituted or unsubstituted silyl groups, carboxy Real groups, halogen atoms, cyano groups, nitro groups, or hydroxyl groups; Ar ¹ , Ar ² , R ⁹ and R ¹⁰ may be substituted with two or more groups as substituents to condensed aryl groups, which are adjacent to each other. The groups may be bonded to form a saturated or unsaturated ring, except that the groups symmetric with respect to the XY axis shown on the anthracene are bonded to the C9 and C10 positions of the anthracene nucleus.)

(V)

(In Formula v, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an alkyl group of C _{1 to} C ₅₀ , C ₃ -C ₅₀ cycloalkyl group, substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C ₆ -C ₅₀ aryl jade Time period, substituted or unsubstituted C ₁ -C ₅₀ alkylamino group, substituted or unsubstituted C ₂ -C ₅₀ alkenyl group, substituted or unsubstituted C ₆ -C ₅₀ arylamino group, substituted or unsubstituted C ₅ to C ₅₀ heteroaryl group or substituted or unsubstituted C ₅ to C ₅₀ heterocycle group; a and b each independently represent an integer of 1 to 5, and when they are 2 or more, R ¹ or R ² They may be the same as or different from each other, and R ¹ or R ² may be bonded to each other to form a ring, and also R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁹ and R ¹⁰ may combine with each other to form a ring; L ¹ is a single bond, -O-, -S-, -N (R)-(where R is C _1- A C ₅₀ alkyl group or a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a C ₂ -C ₅₀ alkylene group, or a C ₆ -C ₅₀ arylene group)

(Vi)

(In the formula (VII), R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ are each independently a hydrogen atom, an alkyl group of C _{1 to} C ₅₀ , C for ₃ ~C ₅₀ cycloalkyl group, C ₆ ~C ₅₀ aryl group, C ₁ ~C ₅₀ alkoxy group, the number of nuclear atoms of 6 to 50 aryloxy group, C ₁ ~C ₅₀ alkylamino group, C ₆ ~ An arylamino group of C ₅₀ , a substituted or unsubstituted heteroaryl group having 5 to 50 nuclear atoms, or a substituted or unsubstituted nuclear atom having 5 to 50 heterocycle groups; c, d, e and f each independently Represent an integer of 1 to 5, and when they are 2 or more, R ¹¹ , R ¹² , R ¹⁶ or R ¹⁷ may be the same or different, and also R ¹¹ , R ¹² , R ¹⁶ or R ¹⁷ May be bonded to each other to form a ring, and R ¹³ and R ¹⁴ , R ¹⁸ and R ¹⁹ may be bonded to each other to form a ring; L ² may be a single bond, —O—, -S-, -N (R) - (wherein R is C ₁ ~C ₅₀ alkyl group or a substituted or unsubstituted C ₆ ~C ₅₀ aryl group a), of C ₂ ~C ₅₀ alkylene group or a C ₆ ~C ₅₀ arylene groups)

[Chemical Formula I]

(In Formula (VIII), A ⁵ , A ⁶ , A ⁷ and A ⁸ are each independently a substituted or unsubstituted biphenyl group or a substituted or unsubstituted naphthyl group.)

[Chemical Formula I]

(In formula (VIII), A ⁹ , A ¹⁰ , A ¹¹ , A ¹² , A ¹³ and A ¹⁴ are each independently a substituted or unsubstituted biphenyl group or an unsubstituted naphthyl group, at least one of which is three or more rings. had have a fused aromatic ring; R ^21, R ²² and R ²³ each independently represent a hydrogen atom, an alkyl group of C ₁ ~C _6, cycloalkyl group of C ₃ ~C _6, alkoxy group of C ₁ ~C _6, C ₅ An aryloxy group of -C _18, an aralkyloxy group of C ₇ -C ₁₈ , an arylamino group of C ₅ -C ₁₆ , a nitro group, a cyano group, an ester group of C ₁ -C ₆ , or a halogen atom )

[Chemical Formula I]

(In the formula (V), R ₁ and R ₂ are each independently a hydrogen atom, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aralkyl group, a substituted or unsubstituted an aryl group of C ₆ ~C _50, a substituted or unsubstituted 5 to 50 nuclear atoms of the heterocyclic group, a substituted or represents an amino group, a cyano group or a halogen atom unsubstituted, R ₁ bonded to different fluorene Each other and R ₂ may be the same as or different from each other, R ₁ and R ₂ bonded to the same fluorene group may be the same or different from each other; R ₃ and R ₄ are each independently a hydrogen atom, a substituted or unsubstituted C ₁ An alkyl group of -C ₅₀ , a substituted or unsubstituted C ₆ -C ₅₀ aralkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, or a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms. R bound to other fluorene groups ₃ and R ₄ may be the same as or different from each other, R ₃ and R ₄ bonded to the same fluorene group may be the same or different from each other, and Ar ₁ and Ar ₂ may be substituted or unsubstituted with a total of three or more benzene rings; A condensed polycyclic aromatic group or a condensed polycyclic heterocyclic group bonded to a fluorene group with a substituted or unsubstituted carbon having a total of three or more benzene rings and heterocycles, and Ar ₁ and Ar ₂ may be the same or different from each other; n Represents an integer of 1 to 10)

[Formula x]

(In Formula x, A ₁ and A ₂ are each independently a substituted or unsubstituted C ₆ -C ₂₀ aryl group or a group derived therefrom, wherein the aryl group is a substituted or unsubstituted C ₆ -C ₅₀ of Aryl group, substituted or unsubstituted C ₁ -C ₅₀ alkyl group, substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C _{6-C 50} aralkyl group, substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms, substituted or unsubstituted arylthio group having 5 to 50 nuclear atoms, substituted or unsubstituted C ₁ to C ₅₀ An alkoxycarbonyl group, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group and a hydroxyl group may be substituted with one or two or more substituents, and two or more substituents If substituted with these substitutions Might be to each other equal to and or be different, and also form a cyclic structure among the substituents adjacent to each other be connected to each other, saturated or unsaturated, _{and; R 1, R 2, R} 3, R 4, R 5, R 6, R ₇ and R ₈ are each independently a hydrogen atom, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 50 nuclear atoms, a substituted or unsubstituted C ₁ -C ₅₀ alkyl groups, substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl groups, substituted or unsubstituted C ₁ -C ₅₀ alkoxy groups, substituted or unsubstituted C ₆ -C ₅₀ aralkyl groups, substituted or unsubstituted Substituted aryloxy group having 5 to 50 nuclear atoms, substituted or unsubstituted arylthio group having 5 to 50 nuclear atoms, substituted or unsubstituted C ₁ to C ₅₀ alkoxycarbonyl group, substituted or unsubstituted silyl group , Carboxyl group, halogen atom, cyano group, nitro group and hydroxyl group Is selected)

(Xi)

(In Formula xi, A ₁ , A ₂ , R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently as defined in Formula x, except that At the C9 and C10 positions of the anthracene, a group symmetrical with respect to the XY axis indicated on the anthracene does not bind)

Among the host materials described above, an anthracene derivative is preferable, a monoanthracene derivative is more preferable, and an asymmetric anthracene derivative is particularly preferable.

As a dopant material that can be used in combination with the compound represented by Formula F1 or Formula F2, IDE102, IDE105, and C545T, available from Hayamibara, may be used as fluorescent dopants, and phosphorescent dopants. As the red phosphorescent dopant PtOEP, RD61 manufactured by UDC, green phosphorescent dopant Ir (PPy) 3 (where PPy is 2-phenylpyridine), F2Irpic which is a blue phosphorescent dopant, and an optical dopant RD 61 which is red in UDC can be used. N-methylquinacridone (MQD), coumarine derivatives and the like can also be used. Further, a metal-ligand complex compound represented by the following formula (a) may also be used.

(A)

M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³

(In the formula a, M ¹ is selected from the group consisting of metal elements of Group 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the periodic table; L ¹⁰¹ , L ¹⁰² , L ¹⁰³ are each selected from the following structures as ligands;

,

또는

이며, R₂₃₁내지 R₂₄₂는 서로 독립적으로 수소, 중수소, 할로젠이 치환되거나 치환되지 않은 C₁∼C₃₀의 알킬기, C₁∼C₃₀의 알콕시기, 할로젠이 치환 또는 비치환된 C₆∼C₃₀의 아릴기, 시아노가 치환 또는 비치환된 C₅∼C₃₀의 시클로알킬기이거나, 인접한 치환체와 C₃∼C₁₂의 알킬렌 또는 C₃∼C₁₂의 알케닐렌으로 연결되어 스피로 고리 또는 축합고리를 형성할 수 있거나, R₂₀₇또는 R₂₀₈과 C₃∼C₁₂의 알킬렌 또는 C₃∼C₁₂의 알케닐렌으로 연결되어 포화 또는 불포화의 축합고리를 형성할 수 있다.At this time, the R _201, R _202, and R ₂₀₃ each represent a hydrogen atom, an alkyl group with or without halogen substituent _{C 1 ~C 30, C 1 ~C} 30 alkyl is optionally substituted C ₁ ~C ₅₀ of An aryl group, or a halogen atom; R ₂₀₄ to R ₂₁₉ independently represent a hydrogen atom, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, a substituted or unsubstituted C ₃ to C ₃₀ cycloalkyl group, a substituted or unsubstituted C ₂ ~C ₃₀ uial Kane group, a substituted or unsubstituted mono or a substituted or unsubstituted aryl group, a substituted or unsubstituted C ₆ ~C ₃₀ ring-di (C ₁ ~C ₃₀ alkyl) amino group, a substituted or unsubstituted mono- or di-ring - (C ₆ ~C ₃₀ aryl) amino group, a SF5, substituted or unsubstituted tree (C ₁ ~C ₃₀ of alkyl) silyl group, a substituted or unsubstituted ring Di (C _{1 to} C ₃₀ alkyl) (C _{6 to} C ₃₀ aryl) silyl, substituted or unsubstituted tri (C _{6 to} C ₃₀ aryl) silyl, cyano or halogen atom; R ₂₂₀ to R ₂₂₃ independently represent a hydrogen atom, a deuterium atom, a C _{1 to} C ₃₀ alkyl group optionally substituted by halogen, or a C _{6 to} C ₃₀ substituted or unsubstituted C _{1 to} C ₃₀ alkyl Lt; / RTI > R ₂₂₄ and R ₂₂₅ independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, or a halogen atom, or R ₂₂₄ and R ₂₂₅ is connected by including the fused ring does not contain, or C ₃ ~C ₁₂ alkylene or C ₃ ~C ₁₂ of alkenylene to form an aliphatic ring, or a monocyclic or multi-fused ring; R ₂₂₆ is a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, a substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group, or a halogen atom ; R ₂₂₇ to R ₂₂₉ independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, or a halogen atom; Q is

,

or

And R ₂₃₁ to R ₂₄₂ are independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₃₀ alkyl group, a substituted or unsubstituted C ₁ -C ₃₀ alkoxy group, a substituted or unsubstituted C ₆ aryl groups ~C _30, cyano furnace or a cycloalkyl group of the substituted or unsubstituted C ₅ ~C _30, alkenylene of an adjacent substituent via C ₃ ~C ₁₂ alkylene or C ₃ ~C ₁₂ of the spiro ring or May form a condensed ring, or may be connected to R ₂₀₇ or R ₂₀₈ by C ₃ -C ₁₂ alkylene or C ₃ -C ₁₂ alkenylene to form a saturated or unsaturated condensed ring.

The doping concentration is not particularly limited, but the content of the dopant is usually 0.01 to 15 parts by weight based on 100 parts by weight of the host. The thickness of the light emitting layer may be about 100 A to 1000 A, preferably 200 A to 600 A, When the thickness of the light emitting layer is less than 100 ANGSTROM, the light emission characteristics may be degraded. When the thickness of the light emitting layer is more than 1000 ANGSTROM, the driving voltage may increase.

When a light emitting compound is used with a phosphorescent dopant in the light emitting layer, a method such as vacuum deposition, spin coating, cast method, LB method, etc. is used on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer. The hole blocking layer HBL can be formed. When the hole blocking layer is formed by a vacuum deposition method or a spin coating method, the conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer. Known hole blocking materials that can be used include, for example, oxadiazole derivatives, triazole derivatives (TAZ), phenanthroline derivatives (BCP), and the like.

The thickness of the hole blocking layer may be about 50 Å to 1000 Å, preferably 100 Å to 300 Å. When the thickness of the hole blocking layer is less than 50 ANGSTROM, the hole blocking characteristics may be deteriorated. When the thickness of the hole blocking layer is more than 1000 ANGSTROM, the driving voltage may increase.

Next, an electron transport layer (ETL) is formed by various methods such as a vacuum evaporation method, a spin coating method, and a casting method.

In the case of forming the electron transporting layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but generally, the conditions are substantially the same as those for forming the hole injection layer. The electron transport layer material serves to stably transport electrons injected from an electron injection electrode, and quinoline derivatives, particularly known materials such as Alq3, TAZ, Balq, PBD and the like may be used.

The thickness of the electron transporting layer may be about 100 ANGSTROM to 1000 ANGSTROM, preferably 200 ANGSTROM to 500 ANGSTROM. When the thickness of the electron transporting layer is less than 100 ANGSTROM, the electron transporting property may be degraded. When the thickness of the electron transporting layer is more than 1000 ANGSTROM, the driving voltage may increase.

Further, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transporting layer, which is not particularly limited. As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li ₂ O, BaO, or the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer. The thickness of the electron injection layer may be about 1 A to 100 A, preferably 5 A to 50 A. If the thickness of the electron injection layer is less than 1 A, the electron injection characteristics may be deteriorated. If the thickness of the electron injection layer exceeds 100 A, the driving voltage may increase.

Finally, the second electrode can be formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like.

The second electrode may be used as a cathode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, or a mixture thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- .

Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic electroluminescent compound according to another embodiment of the present invention is an indazole compound represented by Formula F1 or Formula F2, and more specifically, Compounds 1 to 360 specifically illustrated in the above [First Table Group] are May be included. The details of the compounds are the same as those described for the organic foot and the device described above.

Hereinafter, the synthesis examples and examples of the present invention will be specifically illustrated, but the present invention is not limited to the following synthesis examples and examples. In the following synthesis, the intermediate compound is indicated by adding the serial number to the number of the final product. For example, compound 1 is represented by compound [1], and the intermediate compound of the said compound is described by [1-1] etc.

[Example]

Representative Synthesis Example 1 Synthesis of Compound 1

Preparation of intermediate compound [1-1]

In a nitrogen flask, 100 g (655.39 mmol) of 7-chloro-1H-indazole, 200.5 g (983.09 mmol) of iodine benzene, 55.1 g (983.09 mmol) of potassium hydroxide, 37.4 g (196.61 mmol) of copper iodide, 8- Hydroxyquinoline 95.1 g (655.39 mmol) and 1.5 L of dimethyl sulfoxide were added and stirred at 140 ° C. for 6 hours. After the reaction is completed, the mixture is cooled to room temperature. Pour 1 liter of purified water into the reaction solution to solidify. The resulting solid is filtered and washed with purified water and methanol. The filtered solid was dissolved by adding dichloromethane and filtered through silica. The filtrate was distilled under reduced pressure to prepare 122 g (65%) of an off-white solid compound [1-1] using dichloromethane and hexane.

Preparation of intermediate compound [1-2]

122 g (533.49 mmol) of compound [1-2], 133.5 g (800.2 mmol) of (2-nitrophenyl) boronic acid, 12.3 g (10.6 mmol) of tetrakis (triphenylphosphine) palladium, carbonate in a reaction flask under nitrogen atmosphere 110.6 g (800.2 mmol) of potassium, 120 mL of distilled water and 1.2 L of tetrahydrofuran were added and stirred at 50 ° C for 24 hours. After completion of the reaction, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure, and then a yellow solid intermediate compound [1-2] 87.4 g (52%) was prepared using dichloromethane and methanol. It was.

Preparation of Intermediate Compound [1-3]

87 g (275.9 mmol) of compound [1-2], 145 mL (827.7 mmol) of triethylphosphite, and 200 m of isopropyl benzene were added thereto, and the mixture was stirred at 150 ° C. for 12 hours. After completion of the reaction, the reaction solution is concentrated under reduced pressure. The concentrate was separated and purified through column chromatography to prepare 54.7 g (70%) of an intermediate compound [1-3] as a yellow solid.

Preparation of compound [1]

In a nitrogen atmosphere, 6 g (21.1 mmol) of Compound [1-3] and 120 mL of dimethylformamide are added to the flask, and the mixture is suspended and stirred. Add 1.3 g (31.7 mmol) of sodium hydride to the reaction solution, stir for 20 minutes, add 6 g (533.49 mmol) of 2-chloro-4,6-diphenyltriazine, and stir for 4 hours.After completion of the reaction, add 100 mL of distilled water and add 30 Stir for minutes. The resulting solid is filtered and washed with purified water and methanol. 7.8 g (72%) of the title compound (1) as a white solid was obtained through toluene recrystallization.

Representative Synthesis Example 2 Synthesis of Compound 4

6 g (21.1 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine 7.9 g (23.2 mmol), palladium (II) 94 mg (0.42 mmol) of acetate, 3 g (31.6 mmol) of potassium t-butoxide, and 0.8 mL (0.84 mmol) of 50% tri-t-butylphosphine were stirred under reflux with 100 mL of ethylene for 12 hours. After completion of the reaction, saturated aqueous ammonium solution was poured into the reaction solution and extracted with ethyl acetate. The organic layer is separated, dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure. The concentrated solution was recrystallized from toluene to obtain 8.5 g (68%) of the title compound [4] as a white solid.

Representative synthetic example  3. Synthesis of Compound 98

1) Preparation of Intermediate Compound [98-1]

In the same manner as in Synthesis Example 1, 50 g (327.69 mmol) of 6-chloro-1H-indazole, 100.2 g (491.54 mmol) of iodinebenzene, 27.1 g (491.54 mmol) of potassium hydroxide, and 18.7 g of copper iodide ( 98.31 mmol), 47.5 g (327.68 mmol) of 8-hydroxyquinoline, and 750 mL of dimethylsulfoxide were used to prepare 62 g (yield 66%) of an intermediate compound [98-1] as an off-white solid.

2) Preparation of Intermediate Compound [98-2]

62 g (271.12 mmol) of the intermediate compound [98-1], 43.9 g (324.34 mmol) of 1- (2-aminophenyl) ethanone, 1.2 g (5.42 mmol) of palladium (II) acetate, 56.2 g of potassium carbonate (406.6 mmol), 10.2 mL (10.8 mmol) of 50% tri-t-butylphosphine, and 1 L of toluene were stirred under reflux for 24 hours. After completion of the reaction, saturated aqueous ammonium solution was poured into the reaction solution and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and separated and purified by column chromatography to obtain 60 g (yield 68%) of the intermediate compound [98-2] as a yellow solid.

3) Preparation of Intermediate Compound [98-3]

In a nitrogen atmosphere, 60 g (183.27 mmol) of an intermediate compound and 600 mL of tetrahydrofuran were added to a reaction flask and stirred. 91.6 mL (274.9 mmol) of 3M methylmagnesium chloride was slowly added dropwise to the reactor, followed by stirring at room temperature for 24 hours. After completion of the reaction, the reaction solution was slowly poured into a saturated aqueous ammonium solution and the organic layer was separated with ethyl acetate. The organic layer was separated and dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give 49.1 g (yield 78%) of a yellow intermediate compound.

4) Preparation of Intermediate Compounds [98-4] and [98-5]

In a nitrogen atmosphere, 49 g (142.68 mmol) of an intermediate compound and 500 mL of dichloromethane were added to a reaction flask and stirred. 46.3 mL (713.41 mmol) of sulfonic acid was added to the reactor, followed by stirring at room temperature for 12 hours. After completion of the reaction, saturated aqueous ammonium solution was poured and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 18.5 g (yield 40%) of intermediate compound [98-4] and 19.5 g (yield 42%) of intermediate compound [98-5].

5) Preparation of Compound [98]

In the same manner as in Synthesis Example 2, 6 g (18.43 mmol) of compound [98-4], 7.5 g (22.11 mmol) of 2- (3-chlorophenyl) -4,6-diphenylpyrimidine, and palladium ( II) The desired compound as a white solid using 82 mg (0.36 mmol) of acetate, 2.6 g (27.6 mmol) of potassium t-butoxide, 0.7 mL (0.73 mmol) of 50% tri-t-butylphosphine, 100 mL of xylene 7.8 g (67% yield) were obtained.

Representative synthetic example  4. Synthesis of Compound 113

1) Preparation of Intermediate Compound [113-1]

In the same manner as in Synthesis Example 1, 50 g (318.12 mmol) of 1,6-dihydroferolo [2,3-e] indazole, 71.3 g (349.99 mmol) of iodinebenzene, and 26.7 g of potassium hydroxide ( 477.18 mmol), 18.1 g (95.43 mmol) of copper iodide, 46.1 g (318.12 mmol) of 8-hydroxyquinoline, and 750 mL of dimethyl sulfoxide were separated and purified through column chromatography to give an off-white solid compound [113-1] 38.5 g (52% yield) were prepared.

2) Preparation of Compound [113]

In the same manner as in Synthesis Example 2, 60.6 g (25.72 mmol) of Compound [113-1], and 10.6 g of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (30.86 mmol), 115 mg (0.51 mmol) of palladium (II) acetate, 3.7 g (38.58 mmol) of potassium t-butoxide, 0.5 mL (1.02 mmol) of 50% tri-t-butylphosphine, 100 mL of xylene To give 8.3 g (yield 60%) of the title compound (113) as a white solid.

Compounds of Compounds 1 to 360 were synthesized according to the methods of Representative Synthesis Examples 1 to 4 described above, and the results of nuclear magnetic resonance spectra (NMR) and mass spectrometry (MS) for confirming the structure of the synthesized compounds were shown below. 2 vote group].

[Second group (group)]

Comparative Example 1. Preparation of Comparative Sample 1

Using a compound represented by the formula (a) as a phosphorescent green host, using a compound represented by the formula (c) as a phosphorescent green dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2- yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Thus, an organic light emitting device having the following structure was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a + Compound c (30 nm) / Alq ₃ (30 nm) / LiF ( 0.5 nm) / Al (60 nm).

Anode cut Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm size, and acetone was ultrasonically cleaned in sopropyl alcohol and pure water for 15 minutes, and then UV ozone for 30 minutes. It was used by washing. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Chemical Formula a and a compound represented by Chemical Formula c (doping rate: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Thereafter, an Alq ₃ compound was vacuum-deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in [Table 2]. This is referred to as Comparative Sample 1.

Comparative Example 2. Production of Comparative Sample 2

Using a compound represented by the formula b as a phosphorescent green host, using a compound represented by the formula c as a phosphorescent green dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2- yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Thus, an organic light emitting device having the following structure was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound b + Compound c (30 nm) / Alq ₃ (30 nm) / LiF ( 0.5 nm) / Al (60 nm).

Anode cut Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm size, and acetone was ultrasonically cleaned in sopropyl alcohol and pure water for 15 minutes, and then UV ozone for 30 minutes. It was used by washing. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Chemical Formula a and a compound represented by Chemical Formula c (doping rate: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Thereafter, an Alq ₃ compound was vacuum-deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in [Second Table]. This is called Comparative Sample 2.

Comparative Example 3. Comparative Sample 3 Preparation

C using compound a represented by formula a as a host, compound d represented by formula d as a dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2-yl ) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. An organic light emitting diode having the following structure was fabricated: ITO / 2-TNATA (80nm) / α-NPD (30nm) / Compound a + Compound d (30nm) / Alq3 (30nm) / LiF (0.5nm) / Al (60 nm).

An anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning it in acetone, isopropyl alcohol and pure water for 15 minutes each, Ozone cleaning was used. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound a represented by Formula a and Compound d (10% doped) represented by Formula d were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum deposited on the electron transport layer to prepare an organic light emitting device as shown in [Second Table]. This is referred to as Comparative Sample 3.

Examples 1-326. Sample Preparation

In Comparative Example 1, instead of the light emitting layer phosphorescent host compound a, compounds represented by Chemical Formulas 1 to 360 disclosed in the synthesis examples were used as phosphorescent green host compounds, respectively. And ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / [one of phosphorescent green host compounds 1 to 360 + compound c (10%)] (30 nm) / An organic light emitting diode having a structure of Alq ₃ (30 nm) / LiF (0.5 nm) / Al (60 nm) was manufactured. These are referred to as samples 1 to 326, respectively.

Examples 327-360. Sample Preparation

In Comparative Example 3, compounds of Chemical Formulas 327 to 360 disclosed in Synthesis Example were used as emission layer host compounds instead of compound a as emission layer phosphorescent host compounds. And ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / [one of host compounds 327 to 360 + compound] (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) in the same manner as in Comparative Example 3. An organic light emitting device having a structure of / Al (60 nm) was manufactured. And these are called samples 327-360, respectively.

[Experimental Example] Characteristic evaluation

Experimental Example 1: Evaluation of luminescence characteristics

1) Evaluation of Luminescence Characteristics of Samples 1 to 326

For Comparative Samples 1, 2 and Samples 1 to 326 prepared in Comparative Examples and Examples, the luminous intensity, luminous efficiency, and luminous peak were evaluated using Keithley sourcemeter "2400" and KONIKA MINOLTA "CS-2000", respectively. The results are shown in the following [Table 3]. The samples showed green emission peak values in the 511-517 nm range.

[Group 3]

As confirmed from the above [Third Table], Samples 1 to 326 showed improved luminescence properties compared to Comparative Samples 1 and 2.

2) Evaluation of Luminescence Characteristics of Samples 327 to 360

For Comparative Sample 3 and Samples 327 to 360 prepared in Comparative Examples and Examples, the light emission luminance, light emission efficiency, and light emission peak were evaluated using Keithley SMU 235 and PR650, respectively. Viii). The samples showed red luminescence peak values in the range of 610-616 nm.

[Group 4]

As confirmed from the above [Table 4], samples 327 to 360 exhibited improved luminescence properties as compared to comparison sample 3.

Experimental Example 2: Evaluation of Life Characteristics

1) Evaluation of Life Characteristics of Samples 1 to 326

For Comparative Samples 1 and 2 and Samples 1 to 326 produced in Comparative Examples and Examples, the time at which the life reaches 97% based on 3000 nits was measured using the LTS-1004AC life measuring apparatus of ENC Technology. It was. The results are shown in the following [Table 5].

[Fifth group (group)]

As confirmed from the above [Table 5], Samples 1 to 326 showed improved life characteristics compared to Comparative Samples 1 and 2.

2) Evaluation of Life Characteristics of Samples 327 to 360

For Comparative Sample 3 and Samples 327, 329, 348, 350, 353, and 360 prepared in Comparative Examples and Examples, the intensity of light emission was determined based on the luminance 5000 nit in DC mode using the LTS-1004C life test equipment. Life was assessed with time decreasing to 70% of initial value. The results are shown in the following [Table 6].

[Group 6]

As confirmed from the [Table 6], samples 327, 329, 348, 350, 353, and 360 showed improved life characteristics as compared to comparison sample 3.

Claims (10)

An organic light emitting compound represented by the following Formula F1 or Formula F2:
[Formula F1]

[Formula F2]

In Chemical Formula F1 or F2,
R ₁ , R ₂ , R ₃ , and R ₄ , which are the same as or different from each other, represent a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₅ -C ₄₀ aryl group, or a C ₅ -C ₄₀ heteroaryl group, or R ₁ , R ₂ , R ₃ , and R ₄ may combine two adjacent groups to form a fused C _{5 to} C ₄₀ aryl group;
A ₁ and A ₂ , which are the same or different, represent N or CR ₅ , wherein R ₅ represents a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₅ -C ₄₀ aryl group, or a C ₅ -C ₄₀ heteroaryl group ;
X ₁ and X ₂ , which are the same as or different from each other, represent a single bond, S, O, CR ^a R ^b , SiR ^a R ^b , or N- (L ₃ ) _m -L ₄ ;
L ₁ and L ₃ , which are the same as or different from each other, represent a C ₃ to C ₄₀ cycloalkyl group, or a C _{5 to} C ₄₀ aryl group;
L ₂ and L _4, the same as or different from each other, represent a hydrogen atom, a C ₁ -C ₄₀ alkyl group, a C ₃ -C ₄₀ heterocycloalkyl group, or a C ₅ -C ₄₀ heteroaryl group;
R ^a and R ^b are the same as or different from each other and are a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{5 to} C ₄₀ aryl group, a C _{3 to} C ₄₀ cycloalkyl group, a C _{3 to} C ₄₀ heterocycloalkyl group, or C ₅ It represents a ~C ₄₀ heteroaryl;
m is 0 or 1;
In addition, the heterocycloalkyl or heteroaryl used in the definition of the substituents A ₁ , A ₂ , L ₂ , L ₄ , R ^a , and R ^b may include 1 to 4 heteroatoms selected from O, S, N, and Si. Can,
Also used in the definitions of the substituents R ₁ , R ₂ , R ₃ , R ₄ , A ₁ , A ₂ , L ₁ , L ₂ , L ₃ , L ₄ , R ^a , and R ^b , cycloalkyl, hetero Aryl, or heterocycloalkyl, may be monocyclic or consist of 2 to 7 polycyclic, which monocyclic or polycyclic is deuterium, C ₁ -C ₄₀ alkyl, C ₃ -C ₄₀ cyclo Selected from the group consisting of alkyl, C ₅ -C ₄₀ arylamino, di (C ₅ -C ₄₀ aryl) amino, C ₅ -C ₄₀ aryl, C ₃ -C ₄₀ heterocycloalkyl, and C ₅ -C ₄₀ heteroaryl Aryl or heteroaryl, which may be substituted or unsubstituted with a substituent, and defined as a substituent of the above monocyclic or polycyclic ring, may be substituted with C ₁ -C ₄₀ alkyl, C ₅ -C ₄₀ aryl, and C ₅ -C ₄₀ heteroaryl. It may be substituted or unsubstituted again with a substituent selected from the group consisting of. The method of claim 1,
R ₁ , R ₂ , R ₃ , and R ₄ are the same as or different from each other and are a hydrogen atom, a C ₁ -C ₁₀ alkyl group, a phenyl group, a naphthalenyl group, a pyridyl group, a pyrimidyl group, or a triazinyl group, or R ₁ , R ₂ , R ₃ , and R ₄ are organic light emitting compounds, characterized in that two adjacent groups are bonded to each other to form a fused phenyl group or a condensed naphthalenyl group. The method of claim 1,
A ₁ and A ₂ are the same as or different from each other and represent N or CR ₅ , wherein R ₅ represents a hydrogen atom, a C _{1 to} C ₁₀ alkyl group, or a phenyl group. The method of claim 1,
X ₁ and X ₂ are the same as or different from each other, and a single bond, S, O, CH (C ₁ -C ₁₀ alkyl), C (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl), CH (C _5- C ₁₀ aryl), C (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl), SiH (C ₁ -C ₁₀ alkyl), Si (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ Alkyl), SiH (C ₅ -C ₁₀ aryl), Si (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl) or N- (L ₃ ) _m -L ₄ . The method of claim 1,
L ₁ and L ₃ are the same as or different from each other, a phenylene group, a biphenylene group,

Naphthalenylene group, naphthalenylene naphthalenylene group, anthracenylene group, phenanthrenylene group, fluorenylene group, or

Each of which may be substituted or unsubstituted with a substituent selected from deuterium, C ₁ -C ₁₀ alkyl, phenyl, C ₁ -C ₁₀ alkyl substituted phenyl, biphenyl, and pyridyl;
Q ₁ is O, S, C (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl), C (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl), Si (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl) or Si (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl). The method of claim 1,
L ₂ and L ₄ represent a hydrogen atom, a C ₁ -C ₁₀ alkyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolinyl group, a quinazolinyl group, an indole group, a phenanthridine group, a benzothiazole group,

, ,

or

Which may be unsubstituted or substituted with substituents selected from deuterium, C ₁ -C ₁₀ alkyl, phenyl, deuterium substituted phenyl, C ₁ -C ₁₀ alkyl substituted phenyl, biphenyl, naphthalenyl, and pyridyl, respectively. Can;
Q ₂ , Q ₃ , and Q ₄ are the same as or different from each other and are O, S, NH, N (C ₁ -C ₁₀ alkyl), N (C ₅ -C ₁₀ aryl), C (C ₁ -C ₁₀ alkyl ) (C ₁ -C ₁₀ alkyl), C (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl), Si (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl) or Si (C ₅ -C ₁₀ aryl) (C ₅ -C ₁₀ aryl);
R ^c and R ^d are the same as or different from each other and are C ₁ -C ₄₀ alkyl group, C ₅ -C ₄₀ aryl group, C ₃ -C ₄₀ cycloalkyl group, C ₃ -C ₄₀ heterocycloalkyl group, or C ₅ -C ₄₀ hetero 1 to 5 substituents selected from aryl groups, each of which is deuterium, C ₁ -C ₁₀ alkyl, C ₅ -C ₁₀ aryl, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, or C ₅ Optionally substituted or substituted with 1 to 5 substituents selected from -C ₁₀ heteroaryl;
m is 0 or 1; The method of claim 1,
An organic light emitting compound selected from the group consisting of the following compounds 1 to 360:

A first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode,
The organic light-emitting device of claim 1, wherein the organic layer comprises any one of the organic light emitting compounds selected from the above claims. The method of claim 8,
Wherein the organic film further comprises a known host material, a known dopant material, or a mixture thereof. The method of claim 8,
Wherein the organic layer further comprises at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.