KR101574710B1 - 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. More particularly, the present invention relates to an organic light emitting device capable of realizing excellent light emitting efficiency, light emission luminance, (ETM), a light-emitting layer (EML), and a light-emitting layer (EML) between the first electrode and the second electrode are developed by developing an indazole-based compound and an organic optical device using the same. , Hole transporting layer (HTM), and hole injection layer (HIL), and it is possible to improve the performance such as the efficiency increase and the driving voltage reduction, and maximize the capability as the 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 luminescence properties, but they have disadvantages such as low glass transition temperature and very poor thermal stability, such as 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 luminescent compound which can be applied to an organic photonic device, particularly an organic luminescent device.

A second object of the present invention is to provide an organic luminescent device including the novel indazole-based organic luminescent compound and having a low driving voltage and improved luminous efficiency, luminance, thermal stability and lifetime.

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

[Formula F1]

[Formula F2]

In the above formula (F1) or (F2)

R _1, R _2, R _3, and R ₄ are the same or different and represents hydrogen atom, C ₁ ~C ₄₀ alkyl, C ₅ ~C ₄₀ aryl group, or a C ₅ ~C ₄₀ hetero aryl group, or R ₁ , R ₂ , R ₃ , and R ₄ may form a fused C ₅ -C ₄₀ aryl group by bonding two groups adjacent to each other;

A ₁ and A ₂ are the same or different and 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 are the same or different and each represents 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 , equal to or different from each other, represent a C ₃ -C ₄₀ cycloalkyl group, or a C ₅ -C ₄₀ aryl group;

L ₂ and L ₄ , equal to or different from each other, represent a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{3 to} C ₄₀ heterocycloalkyl group, or a C _{5 to} C ₄₀ heteroaryl group;

R ^a, and R ^b are the same or different and represents hydrogen atom, C ₁ ~C ₄₀ alkyl, C ₅ ~C ₄₀ aryl group, C ₃ ~C ₄₀ cycloalkyl group, a C ₃ ~C ₄₀ heterocycloalkyl group, or C ₅ Lt _; RTI ID = 0.0 > of-C40heteroaryl < / RTI >

m is 0 or 1;

The heterocycloalkyl or heteroaryl used in the definitions of the substituents A ₁ , A ₂ , L ₂ , L ₄ , R ^a and R ^b includes 1 to 4 hetero atoms selected from O, S, N and Si Can,

In addition, 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 aryl, cycloalkyl, heteroaryl used in the definition of R ^b Aryl, or heterocycloalkyl may be monocyclic or may comprise from 2 to 7 polycyclic rings, wherein the single ring or multiple rings may be substituted with one or more substituents selected from the group consisting of deuterium, C ₁ -C ₄₀ alkyl, C ₃ -C ₄₀ cyclo 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 which is further defined as a substituent of said single ring or multiple rings is selected from the group consisting of C ₁ to C ₄₀ alkyl, C _{5 to} C ₄₀ aryl, and C _{5 to} C ₄₀ heteroaryl Lt; / RTI > may be substituted or unsubstituted again with a substituent selected from the group consisting of

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode, wherein the organic layer comprises an indazole-based organic light-emitting compound represented by Formula F1 or Formula F2 .

The organic light emitting device including the indazole-based organic light emitting compound according to the present invention can realize high luminescence efficiency, high luminescence brightness, and remarkably improved luminescence 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. The singular expressions include plural expressions unless the context clearly dictates 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.

(ETM), a light emitting layer (EML), a hole transporting layer (HTM), a hole injecting layer (HIL), and a hole injecting layer (HIL) between the first electrode and the second electrode by developing an organic light emitting compound, ), And to develop materials that improve performance such as efficiency and reduction of driving voltage, and maximize their ability as an OLED material.

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 at least one organic film between the first electrode and the second electrode, wherein the organic film comprises an organic light-emitting compound represented by the following formula (F1) or (F2).

[Formula F1]

[Formula F2]

In the above formula (F1) or (F2)

R _1, R _2, R _3, and R ₄ are the same or different and represents hydrogen atom, C ₁ ~C ₄₀ alkyl, C ₅ ~C ₄₀ aryl group, or a C ₅ ~C ₄₀ hetero aryl group, or R ₁ , R ₂ , R ₃ , and R ₄ may form a fused C ₅ -C ₄₀ aryl group by bonding two groups adjacent to each other;

A ₁ and A ₂ are the same or different and 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 are the same or different and each represents 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 , equal to or different from each other, represent a C ₃ -C ₄₀ cycloalkyl group, or a C ₅ -C ₄₀ aryl group;

L ₂ and L ₄ , equal to or different from each other, represent a hydrogen atom, a C _{1 to} C ₄₀ alkyl group, a C _{3 to} C ₄₀ heterocycloalkyl group, or a C _{5 to} C ₄₀ heteroaryl group;

R ^a, and R ^b are the same or different and represents hydrogen atom, C ₁ ~C ₄₀ alkyl, C ₅ ~C ₄₀ aryl group, C ₃ ~C ₄₀ cycloalkyl group, a C ₃ ~C ₄₀ heterocycloalkyl group, or C ₅ Lt _; RTI ID = 0.0 > of-C40heteroaryl < / RTI >

m is 0 or 1;

The heterocycloalkyl or heteroaryl used in the definitions of the substituents A ₁ , A ₂ , L ₂ , L ₄ , R ^a and R ^b includes 1 to 4 hetero atoms selected from O, S, N and Si Can,

In addition, 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 aryl, cycloalkyl, heteroaryl used in the definition of R ^b Aryl, or heterocycloalkyl may be monocyclic or may comprise from 2 to 7 polycyclic rings, wherein the single ring or multiple rings may be substituted with one or more substituents selected from the group consisting of deuterium, C ₁ -C ₄₀ alkyl, C ₃ -C ₄₀ cyclo 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 which is further defined as a substituent of said single ring or multiple rings is selected from the group consisting of C ₁ to C ₄₀ alkyl, C _{5 to} C ₄₀ aryl, and C _{5 to} C ₄₀ heteroaryl Lt; / RTI > may be substituted or unsubstituted again with a substituent selected from the group consisting of

The inventors of the present invention have found that when R ₁ , R ₂ , R ₃ , R ₄ , A ₁ , A ₂ , X ₁ , X ₂ , L ₁ and L ₃ (ETM), a light emitting layer (EML), a hole transporting layer (HTM), and the like, which can be used as various organic layers between the first electrode and the second electrode, and an organic compound It has been found that when an organic electroluminescent device is developed and used as an organic light emitting device, it is possible to improve the performance such as an increase in efficiency and a driving voltage, and to maximize the ability as an OLED material, It is expected that excellent application efficiency will be obtained when applied to optical devices and optical compound fields.

Hereinafter, the organic luminescent compound represented by Formula F1 or Formula F2 will be described with reference to an organic luminescent device, but the present invention should not be construed as being limited thereto.

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

Substituent groups of the organic luminescent compound represented by Formula F1 or Formula F2 are specifically shown below.

Wherein R ₁ , R ₂ , R ₃ and R ₄ are the same or different and each is a hydrogen atom, a C _{1 to} C ₁₀ alkyl group, a phenyl group, a naphthalenyl group, a pyridyl group, a pyrimidyl group or a triazinyl group, ₁ , R ₂ , R ₃ , and R ₄ may form a fused phenyl group or a condensed (fised) naphthalenyl group by bonding two groups adjacent to each other.

A ₁ and A ₂ are the same or different and each represents 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 or different and are a single bond, S, O, CH (C ₁ -C ₁₀ alkyl), C (C ₁ -C ₁₀ alkyl) (C ₁ -C ₁₀ alkyl) ₅ ~C ₁₀ aryl), C (C ₅ ~C ₁₀ aryl) (C ₅ ~C ₁₀ aryl group), SiH (C ₁ ~C ₁₀ alkyl), Si (C ₁ ~C ₁₀ alkyl) (C ₁ ~C ₁₀ alkyl), SiH (C ₅ ~C ₁₀ aryl), it may represent a 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 or different from each other and represent a phenylene group, a biphenylene group,

, A naphthalenyl group, a naphthalenyl naphthalenyl group, an anthracenyl group, a phenanthrenylene group, a fluorenylene group, or

A represents, also, each of deuterium, C ₁ ~C ₁₀ alkyl, phenyl, and may be unsubstituted or substituted with C ₁ ~C ₁₀ alkyl-substituted phenyl, biphenyl, and a substituent selected from pyridyl.

Wherein 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 may represent 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.Wherein L ₂ and L _{4 each} 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,

,

,

or

Each of which is optionally substituted with a substituent selected from deuterium, C ₁ -C ₁₀ alkyl, phenyl, deuterium substituted phenyl, C ₁ -C ₁₀ alkyl substituted phenyl, biphenyl, naphthalenyl, and pyridyl, .

Wherein Q ₂ , Q ₃ and Q ₄ are the same or different and are selected from 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 shows an aryl group).

Wherein R ^c and R ^d are the same or different as C ₁ ~C ₄₀ alkyl, C ₅ ~C ₄₀ aryl group, C ₃ ~C ₄₀ cycloalkyl group, a C ₃ ~C ₄₀ heterocycloalkyl group, or C ₅ ~C ₄₀ And each of which is optionally substituted with one or more substituents selected from the group consisting of deuterium, C ₁ -C ₁₀ alkyl, C ₅ -C ₁₀ aryl, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ heterocycloalkyl, C ₅ ~C ₁₀ heteroaryl group may be unsubstituted or substituted with 1 to 5 substituents selected from.

M means the number of L _{1. When} m = 0, it means that L ₁ does not exist, and when m = 0, L ₁ means that L ₁ exists.

In more detail, according to one embodiment of the present invention, the organic luminescent compound used in the organic light emitting device of the present invention has indazole as a basic skeleton, and specifically, for example, as shown in the following [first group (s) Compounds 1 through 360 may be included, but the present invention is not limited thereto:

[First group (group)]

The organic electroluminescent compound represented by Formula F1 or Formula F2 according to the present invention can be synthesized using a conventional synthetic method, and a more detailed synthesis route of the compound can be found in Synthesis Examples 1 to 4 below.

The organic luminescent compound represented by the above formula (F1) or (F2) is suitable for use in an organic film of an organic optical device, particularly a hole transporting layer, a hole injecting layer, an electron transporting 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 compound layer interposed between the first electrode and the second electrode, wherein the organic compound layer includes at least one organic electroluminescent compound selected from Formula F1 or Formula F2.

The organic electroluminescent device according to the present invention may further include at least one compound represented by Formula F1 or Formula F2, and at the same time, a conventional host material, a conventional 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 contains at least one phosphorescent dopant as an emitting host, with at least one organic light emitting compound selected from the compounds represented by the formulas F1 and F2 , And the luminescent dopant is not particularly limited.

In the organic electroluminescent device of the present invention, the organic electroluminescent device preferably includes at least one organic electroluminescent compound selected from the compounds represented by the above-mentioned formulas F1 and F2, and at the same time, one selected from the group consisting of an arylamine-based compound or a styrylarylamine- The above compound may further be included.

Further, in the organic light emitting device of the present invention, in addition to one or more organic luminescent compounds selected from the compounds represented by the above-mentioned formulas F1 or F2 in the organic material layer, Group 1, Group 2, Group 4, d-transition element, and 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 is formed on a substrate by a vapor deposition method, a sputtering method, or the like 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 Formula F1 or 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 Formula F1 or 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.

The light emitting layer may include a compound represented by Formula F1 or Formula F2 according to the present invention, as described above. At this time, the compound represented by Formula F1 or Formula F2 may be used together with a suitable known host material, or may be used together with a known dopant material. It is also possible to use the compound represented by the above formula (F1) or (F2) alone.

Examples of the host material usable in combination with the compound represented by Formula F1 or Formula F2 include tris (8-hydroxyquinolate aluminum (Alq3), 4,4'-N, N'-dicarbazole- Biphenyl (CBP), poly (n-vinylcarbazole) (PVK), etc. As the host material, an asymmetric anthracene derivative represented by the following formula (i), an asymmetric monoanthracene derivative represented by the following formula An asymmetric pyrene derivative represented by the following formula (iii), an asymmetric anthracene derivative represented by the following formula (iv), an anthracene derivative represented by the following formula (v), an anthracene derivative represented by the following formula (vi), a spirofluorene derivative represented by the following formula , A condensed ring-containing compound represented by the following formula (X), a fluorene compound represented by the following formula (X), an anthracene represented by the following formula (X) A compound having a central skeleton, or a compound having an anthracene center skeleton represented by the following formula (xi) wherein A ₁ and A ₂ in the above formula (x) are substituted with different groups.

(I)

(I in the formula, Ar is a substituted or unsubstituted condensed aryl group of C ₁₀ ~C ₅₀ a; Ar 'is a substituted or unsubstituted C ₆ ~C ₅₀ aryl group, and; 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 , A substituted or unsubstituted C ₆ to C ₅₀ aralkyl group, a substituted or unsubstituted aryloxy group having 6 to 50 nuclear atoms, an arylthio group having 6 to 50 substituted or unsubstituted nuclear atoms, hwandoen c ₁ ~C ₅₀ alkoxy group to a carbonyl group, a carboxyl group, a halogen atom, a cyano group, a nitro to the, or a hydroxyl group, and; a, b and c are each independently an integer of 0 to 4; n Is an integer of 1 to 3, and when n is 2 or 3, the symbols in [] may be the same or different)

(Ii)

(In the formula ⅱ, Ar ¹ and Ar ² are each independently a substituted or unsubstituted C ₆ ~C ₅₀ aryl group; and m and n is an integer from 1 to 4, respectively, provided that m = n = 1 Ar when the binding position of the ^first and the benzene ring of Ar ² is symmetrical, the Ar ¹ and Ar ² are not the same, m or n is for 2 to 4 integer, the m and n are different integers; R ^1, R 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, A substituted or unsubstituted C ₁ to C ₅₀ alkyl group, a substituted or unsubstituted C ₃ to C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₁ to C ₅₀ alkoxy 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)

Wherein Ar and Ar 'are each independently a substituted or unsubstituted, primary C _{6 to} C ₅₀ aryl group; 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 bonding positions on Ar and Ar', the substitution positions of L and L 'or Ar and Ar' in the pyrene are C1 and C6 Position, or C2 and C7 positions.]

[Chemical Formula (iv)

(In the formula ⅳ, A ¹ and A ² are each independently a substituted or unsubstituted condensed aryl group of C ₀ and ₁₀ ~C2; C ₆ Ar ¹ and Ar ² each independently represent a hydrogen atom or a substituted or unsubstituted Wherein _each of R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ is independently a hydrogen atom, a substituted or unsubstituted C 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 unsubstituted alkoxy group, a substituted or unsubstituted C ₆ ~C ₅₀ aralkyl group, a substituted or beach aryloxy be unsubstituted 6 to 50 nuclear atoms, a substituted or unsubstituted An arylthio group having 6 to 50 nuclear atoms, a substituted or unsubstituted C ₁ to C ₅₀ alkoxycarbonyl group, a substituted or unsubstituted silyl group, A halogen atom, a cyano group, a nitro group or a hydroxyl group; Ar ¹ , Ar ² , R ⁹ and R ¹⁰ are substituents on the condensed aryl group, and a plurality of two or more groups may be substituted, Groups may be bonded to form a saturated or unsaturated ring except that a group symmetrical with respect to the XY axis represented by the anthracene is bonded to the C9 and C10 positions of the anthracene nucleus.

(V)

(Wherein 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 C _{1 to} C ₅₀ alkyl group, a cycloalkyl group of C ₃ ~C _50, a substituted or unsubstituted C ₆ ~C ₅₀ aryl group, a substituted or unsubstituted alkoxy group of unsubstituted C ₁ ~C _50, a substituted or unsubstituted C ₆ ~C ₅₀ aryl oxide A substituted or unsubstituted C ₁ to C ₅₀ alkylamino group, a substituted or unsubstituted C ₂ to C ₅₀ alkenylene group, a substituted or unsubstituted C ₆ to C ₅₀ arylamino group, a substituted or unsubstituted C ₅ ~C ₅₀ hetero aryl group or a substituted or represents a heterocycle of the unsubstituted C ₅ ~C _50; a and b independently represent an integer of 1 to 5, when they are more than ^one R 2 together, or R ² respectively, R ¹ and R ² may be bonded to each other to form a ring, and R ³ and R ⁴ , R ⁵ and R ⁶ may be the same or different, , R ⁷ and R ^8, R ⁹ and R ¹⁰ may also be bonded to each other to form a ring and; L ¹ is a single bond, -O-, -S-, -N (R ) - ( wherein R is C ₁ ~ C ₅₀ alkyl group or a substituted or represents a group of the unsubstituted aryl group of C ₆ ~C _50), C ₂ ~C ₅₀ alkylene group or C ₆ ~C ₅₀ arylene)

(Vi)

(Wherein R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ and R ²⁰ each independently represent a hydrogen atom, a C _{1 to} C ₅₀ alkyl group, 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 ~ c ₅₀ aryl group, a substituted or unsubstituted nuclear atoms of 5 to 50 heteroaryl group or a substituted or represents a group of unsubstituted nuclear atoms of 5 to 50 heterocycle; c, d, e and f are each independently R ¹¹ , R ¹² , R ¹⁶ , or R ¹⁷ may be the same or different from each other and R ¹¹ , R ¹² , R ¹⁶ or R ¹⁷ may be the same or different from each other. R ¹³ and R ¹⁴ , and R ¹⁸ and R ¹⁹ may be bonded to each other to form a ring; L ² represents 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 < / RTI > arylene group)

[Chemical Formula I]

(Wherein 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]

(Wherein 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, 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 aryloxy ~C _18, C ₇ ~C ₁₈ aralkyl oxy group, C ₅ ~C ₁₆ aryl group, a represents an ester group or a halogen atom of a group, a cyano group, C ₁ ~C _6-nitro of the )

[Chemical Formula I]

(Wherein 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 A C ₆ -C ₅₀ aryl group, a substituted or unsubstituted heterocyclic group having 5 to 50 nuclear atoms, a substituted or unsubstituted amino group, a cyano group or a halogen atom, and R ₁ It may be the same as each other or different from each other and each other, and R _2, the same fluorene R ₁ and R ₂ that is bonded to fluorene may be the same or different from each other; R ₃ and R ₄ are each independently a hydrogen atom, substituted or unsubstituted C ₁ alkyl ~C _50, a substituted or unsubstituted aralkyl group unsubstituted C ₆ ~C _50, substituted or unsubstituted C ₆ ~C ₅₀ aryl group or a substituted or represents a group of unsubstituted 5 to 50 nuclear atoms heterocycle , R < RTI ID = 0.0 > ₃ and R ₄ may be the same or different and R ₃ and R ₄ bonded to the same fluorene group may be the same or different; Ar ₁ and Ar ₂ each independently represent a substituted or unsubstituted benzene ring having a total of 3 or more benzene rings, A condensed polycyclic aromatic group or a condensed polycyclic heterocyclic group which is a substituted or unsubstituted carbon having a total of three or more benzene rings and a heterocyclic ring bonded to a fluorene group and Ar ₁ and Ar ₂ may be the same or different from each other; Represents an integer of 1 to 10)

[Formula x]

Wherein A ₁ and A ₂ are each independently a substituted or unsubstituted C ₆ -C ₂₀ aryl group or a group derived therefrom and the aryl group is a substituted or unsubstituted C ₆ -C ₅₀ A substituted or unsubstituted C ₁ to C ₅₀ alkyl group, a substituted or unsubstituted C ₃ to C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₁ to C ₅₀ alkoxy group, a substituted or unsubstituted C ₆ ~C ₅₀ aralkyl group, a substituted or unsubstituted 5 to 50 nuclear atoms aryloxy, substituted or unsubstituted coming nuclear atoms of 5 to 50 Im aryl, substituted or unsubstituted C ₁ ~C ₅₀ An alkoxycarbonyl group of 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group and a hydroxyl group, Lt; RTI ID = 0.0 > 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 to C ₅₀ aryl group, a substituted or unsubstituted heteroaryl group having 5 to 50 nucleus atoms, a substituted or unsubstituted C ₁ to C ₅₀ alkyl group, a substituted or unsubstituted cycloalkyl group of unsubstituted C ₃ ~C _50, a substituted or unsubstituted C ₁ ~C ₅₀ alkoxy group, a substituted or unsubstituted C ₆ ~C ₅₀ aralkyl group, a substituted or unsubstituted An arylthio group having 5 to 50 nuclear atoms, a substituted or unsubstituted arylthio group having 5 to 50 ring atoms, a substituted or unsubstituted C ₁ to C ₅₀ alkoxycarbonyl group, a substituted or unsubstituted silyl group , A carboxyl group, a halogen atom, a cyano group, a nitro group and a hydroxyl group / RTI >

(Xi)

(Was in the formula _{xi, A 1, A 2,} R 1, R 2, R 3, R 4, R 5, R 6, R 7 and R ₈ are as defined in the general formula x are each independently, just the central The C9 and C10 positions of the anthracene are not bonded to groups symmetrical with respect to the XY axis shown in the anthracene phase)

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 usable in combination with the compound represented by the formula (F1) or (F2), IDE102, IDE105 available from Idemitsu Co., Ltd. and C545T available from Hayashibara Co., Ltd., which are available as a fluorescent dopant, A red phosphorescent dopant PtOEP, UDC RD61, a green phosphorescent dopant Ir (PPy) 3 (PPy is 2-phenylpyridine), a blue phosphorescent dopant F2Irpic, and a UDC reddish optical dopant RD61. 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 above formula a, M ¹ is selected from the group consisting of a metal element 7 Group 8 Group 9 Group, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 the Periodic Table; L ^101, L ¹⁰² and 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 luminescent compound is used together with a phosphorescent dopant in the luminescent layer, a method such as vacuum deposition, spin coating, casting, LB or the like is performed on the luminescent layer to prevent the triplet excitons or holes from diffusing into the electron transporting 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 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-based compound represented by Formula F1 or Formula F2, more specifically, Compound 1 to 360 specifically exemplified in [First Group (s) . The details of the compounds are the same as those described for the organic foot and the device described above.

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

[Example]

Representative Synthesis Example 1. Synthesis of Compound 1

Preparation of intermediate compound [1-1]

100 g (655.39 mmol) of 7-chloro-1H-indazole, 200.5 g (983.09 mmol) of iodobenzene, 55.1 g (983.09 mmol) of potassium hydroxide and 37.4 g (196.61 mmol) of copper iodide were placed in a reaction flask in a nitrogen atmosphere, 95.1 g (655.39 mmol) of hydroxyquinoline and 1.5 L of dimethylsulfoxide were added, and the mixture was stirred at 140 占 폚 for 6 hours. After completion of the reaction, the reaction mixture is cooled to room temperature. 1 L of purified water is poured into the reaction solution to solidify. The resulting solid is filtered and washed with purified water and methanol. Dissolve the filtered solid with dichloromethane, and filter through silica. The filtrate was distilled under reduced pressure, and dichloromethane and hexane were used to prepare 122 g (65%) of an intermediate compound [1-1] as a off-white solid.

Preparation of intermediate compound [1-2]

In a nitrogen flask, 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, 110.6 g (800.2 mmol) of potassium, 120 mL of distilled water and 1.2 L of tetrahydrofuran were added, and the mixture was stirred at 50 DEG C for 24 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and 87.4 g (52%) of intermediate compound [1-2] as a yellow solid was produced using dichloromethane and methanol Respectively.

Preparation of intermediate compound [1-3]

87 g (275.9 mmol) of the compound [1-2], 145 mL (827.7 mmol) of triethylphosphite and 200 m of isopropylbenzene were placed in a reaction flask and 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 by column chromatography to obtain 54.7 g (70%) of intermediate compound [1-3] as a yellow solid.

Preparation of compound [1]

In a nitrogen atmosphere, 6 g (21.1 mmol) of the compound [1-3] and 120 mL of dimethylformamide are added to the reaction flask and the suspension is stirred. After stirring for 20 minutes, 6 g (533.49 mmol) of 2-chloro-4,6-diphenyltriazine was added and stirred for 4 hours. After completion of the reaction, 100 mL of distilled water was added, and 30 Min. The resulting solid is filtered and washed with purified water and methanol. The filtered solid was recrystallized from toluene to obtain 7.8 g (72%) of the target compound [1] as a white solid.

Representative Synthesis Example 2. Synthesis of Compound 4

To the reaction flask were added 6 g (21.1 mmol) of the compound [1-3], 7.9 g (23.2 mmol) of 2- (3-chlorophenyl) (0.842 mmol) of 50% tri-t-butylphosphine in 100 mL of dichloromethane under reflux for 12 hours. After completion of the reaction, saturated aqueous ammonium solution is poured into the reaction solution and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure. The concentrate was recrystallized from toluene to obtain 8.5 g (68%) of the target compound [4] as a white solid.

Representative synthetic example  3. Synthesis of Compound 98

1) Preparation of intermediate compound [98-1]

50 g (327.69 mmol) of 6-chloro-1H-indazole, 100.2 g (491.54 mmol) of iodobenzene, 27.1 g (491.54 mmol) of potassium hydroxide and 18.7 g 62% yield (66% yield) of an intermediate compound [98-1] as a off-white solid was prepared using 47.5 g (327.68 mmol) of 8-hydroxyquinoline and 750 mL of dimethylsulfoxide.

2) Preparation of intermediate compound [98-2]

To the reaction flask were added 62 g (271.12 mmol) of 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 (406.6 mmol), 10.2 mL (10.8 mmol) of 50% tri-t-butylphosphine and 1 L of toluene was refluxed 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 then purified by column chromatography to obtain 60 g (yield 68%) of 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 intermediate compound [98-2] 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, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 49.1 g (yield 78%) of yellow intermediate compound [98-3].

4) Preparation of intermediate compounds [98-4], [98-5]

In a nitrogen atmosphere, 49 g (142.68 mmol) of intermediate compound [98-3] and 500 mL of dichloromethane were added to a reaction flask and stirred. Sulfonic acid (46.3 mL, 713.41 mmol) was added to the reactor and stirred at room temperature for 12 hours. After completion of the reaction, the saturated aqueous ammonium solution was poured out 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 then purified by column chromatography to obtain 18.5 g (yield: 40%) of intermediate compound [98-4] as a white solid and 19.5 g (yield: 42%) of intermediate compound [98-5].

5) Preparation of compound [98]

6 g (18.43 mmol) of the compound [98-4], 7.5 g (22.11 mmol) of 2- (3-chlorophenyl) -4,6-diphenylpyrimidine, Ⅱ) To a solution of the title compound as a white solid (82 mg, 0.36 mmol), potassium t-butoxide (2.6 g, 27.6 mmol), 50 mL of tri- [98] 7.8 g (yield 67%) was obtained.

Representative synthetic example  4. Synthesis of Compound 113

1) Preparation of intermediate compound [113-1]

50 g (318.12 mmol) of 1,6-dihydropellolo [2,3-e] indazole, 71.3 g (349.99 mmol) of iodobenzene and 26.7 g The intermediate compound [113-1] was obtained as a off-white solid by a column chromatography using 18.1 g (95.43 mmol) of copper iodide, 46.1 g (318.12 mmol) of 8-hydroxyquinoline and 750 mL of dimethylsulfoxide, 38.5 g (yield 52%) was prepared.

2) Preparation of compound [113]

6 g (25.72 mmol) of the compound [113-1] and 10.6 g of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine were obtained in the same manner as in the above- (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- To obtain 8.3 g (yield 60%) of the target compound [113] as a white solid.

The compounds 1 to 360 were synthesized according to the methods of Representative Synthesis Examples 1 to 4, and the results of nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS) 2 group (group)].

[Second group (group)]

Comparative Example 1. Preparation of Comparative Sample 1

Wherein the compound represented by the following formula (a) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) / LiF (30 nm) / compound (30 nm) / compound a + compound 30 nm / ITO / 2-TNATA 0.5 nm) / Al (60 nm).

The 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 and ultrasonically cleaning the acetone for 15 minutes each in small propyl alcohol and pure water, Washed and used. 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, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Formula (a) and a compound represented by Formula (c) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq ₃ 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 injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to produce an organic light emitting device as shown in [second group (group)]. This is referred to as Comparative Sample 1.

Comparative Example 2. Production of Comparative Sample 2

Wherein the compound represented by the following formula (b) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) / LiF (30 nm) / compound (30 nm) / compound (30 nm) / ITO / 2-TNATA 0.5 nm) / Al (60 nm).

The 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 and ultrasonically cleaning the acetone for 15 minutes each in small propyl alcohol and pure water, Washed and used. 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 the formula (a) and a compound represented by the formula (c) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq ₃ 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 injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in [second group (group)]. This is referred to as Comparative Sample 2.

Comparative Example 3. Production of Comparative Sample 3

C 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2-yl) is used as a host, using a compound represented by the following formula a as a host and a compound d represented by the following formula ) -N-phenylamino) -triphenylamine was used as a hole injection layer material and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / Al (30 nm) / compound a + compound d (30 nm) / ITO / 2-TNATA (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 30 nm thick light emitting layer. 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 injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in [second group (group)]. This is referred to as Comparative Sample 3.

Examples 1 to 326. Sample preparation

In Comparative Example 1, the phosphorescent host compound a was used instead of the phosphorescent host compound a in the synthesis examples. (30 nm) / [phosphorescent green host compound 1 to 360 + compound c (10%)] (30 nm) /? -NPD An organic light emitting device having a structure of Alq ₃ (30 nm) / LiF (0.5 nm) / Al (60 nm) was fabricated. These are referred to as Samples 1 to 326, respectively.

Examples 327 to 360. Sample preparation

In Comparative Example 3, instead of Compound a as the phosphorescent host compound, the compounds of Formulas 327 to 360 described in the above Synthesis Examples were used as the host compound in the light emitting layer, respectively. (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / [ITN / 2-TNATA (80 nm) /? -NPD (30 nm) / [one of the host compounds 327 to 360 + compound] / Al (60 nm) was fabricated. These are referred to as Samples 327 to 360, respectively.

[Experimental Example] Characteristic evaluation

Experimental Example 1: Evaluation of luminescence characteristics

1) Evaluation of luminescence characteristics of Samples 1 to 326

The luminescence brightness, luminescence efficiency and luminescence peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 1 and 2 and Samples 1 to 326 prepared in the above Comparative Examples and Examples, respectively , And the results are shown in the following [third group (group)]. The samples showed green emission peak values in the 511-517 nm range.

[Group 3]

Samples 1 to 326 exhibited improved luminescence properties as compared to Comparative Samples 1 and 2, as can be seen from the [third set of group (s)].

2) Evaluation of luminescence characteristics of Samples 327 to 360

The emission luminance, the luminous efficiency, and the emission peak were evaluated using Keithley SMU 235 and PR650, respectively, for Comparative Sample 3 and Samples 327 to 360 prepared in the above Comparative Examples and Examples, respectively. Group)]. The samples showed red emission peak values in the 610-616 nm range.

[Group 4]

Samples 327 to 360 exhibited improved luminescence properties as compared to Comparative Sample 3, as confirmed from [fourth set of group (s)] above.

Experimental Example 2: Evaluation of Life Characteristic

1) Evaluation of life characteristics of Samples 1 to 326

For Comparative Samples 1 and 2 and Samples 1 to 326 produced in the above Comparative Examples and Examples, the time at which the life span reached 97% based on 3000 nits was measured using an LTS-1004AC life measuring device manufactured by ENC Technologies, Inc. Respectively. The results are shown below in the fifth group (group).

[Fifth group (group)]

Samples 1 to 326 exhibited improved lifespan characteristics as compared to Comparative Samples 1 and 2, as confirmed from [fifth set of group (s)] above.

2) Evaluation of lifetime characteristics of samples 327 to 360

For the comparative sample 3 and the samples 327, 329, 348, 350, 353, and 360 manufactured in the comparative example and the example, the intensity of light emission in the DC mode using the LTS-1004C life- The lifetime was evaluated by a time which decreased to 70% of the initial value. The results are shown below in the sixth group (group).

[Group 6]

Samples 327, 329, 348, 350, 353, and 360 showed improved lifetime characteristics as compared to Comparative Sample 3, as confirmed from [sixth set of group (s)

Claims (10)

Wherein the organic compound is selected from the group consisting of compounds 1-84, 90-92, 98-106, 109-112, 159-168, and 186-197.

delete delete delete delete delete delete A first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode,
Wherein the organic layer comprises the organic light-emitting compound of claim 1. 9. The method of claim 8,
Wherein the organic film further comprises a known host material, a known dopant material, or a mixture thereof. 9. 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.