WO2015068987A1 - Novel organic compound, and organic electroluminescent element and electronic device comprising same - Google Patents

Abstract

Provided are an organic compound represented by chemical formula 1 in the specification (see image in the specification) and an organic electroluminescent element comprising the same.

Description

Novel organic compounds, organic electroluminescent devices and electronic devices comprising the same

The present invention relates to a novel organic compound, an organic light emitting display device, and an electronic device including the same.

In general, an organic electric device refers to a device that requires charge exchange between an electrode and an organic material using holes and electrons. Examples of organic electric devices include organic transistors, organic solar cells, organic photoconductors (OPCs), and organic light emitting devices, all of which require light emitting materials, electron injection or transport materials, hole injection or transport materials to drive the devices. Do.

In the organic electric device, the light emitting material is the most important material that determines the performance of the light emission efficiency and life. There are several characteristics required for such light emitting materials, such as high quantum fluorescence yield in solid state, high mobility of electrons and holes, not easy decomposition during vacuum deposition, uniform film formation, It should be stable.

Materials used as the organic material layer in the organic electric element may be divided into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function. In the case of using only one material as a light emitting material, the maximum light emission wavelength may be shifted to a long wavelength due to the interaction of molecules, and thus color purity may be reduced or efficiency may be reduced due to the light emission attenuation effect. As the light emitting material, a host / dopant system may be used. When a small amount of dopant having a smaller energy band gap than the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transferred to the dopant to emit high efficiency light, and at this time, the wavelength of the host is in accordance with the wavelength of the dopant. Will move. That is, light emission of a desired wavelength can be obtained according to the type of dopant to be used.

U.S. Patent No. US5153073 discloses an electroluminescent device using a pyrene-based compound substituted with a diphenyl amine derivative, but the blue color purity is often lowered to give a bluish green light, but the efficiency when blue light emission occurs. There is a disadvantage that the brightness is lower.

In US Patent No. 7,053,255 as a blue light emitting material, the center has a diphenylanthracene structure, and a blue light emitting compound in which an aryl group is substituted at the end and an organic light emitting device using the same are disclosed, but the light emitting efficiency and luminance are not sufficient. There was this.

In addition, WO 2005/108348 A1 discloses aromatic amine derivatives in which a substituted or unsubstituted diphenylamine group is directly substituted with a pyrene-based compound, but a light emission wavelength other than pure blue because the aryl or alkyl group is directly substituted in the pyrene ring. There is a problem of bluish green light moved to this long wavelength.

Meanwhile, US Patent Publication No. 7,233,019, Korean Patent Publication No. 2006-0006760, Korean Patent Registration No. 10-0852328, Korean Patent Registration No. 10-0874472, and Korean Patent Publication No. 2011-0121147 An organic light emitting display device using anthracene and pyrene-based compounds has been disclosed, but it is difficult to realize deep blue due to the low color purity of blue, and the emission wavelength is shifted toward the long wavelength due to the decrease in color purity depending on the driving time. Is increased, but does not satisfy the pure blue color, there is a problem that it is not easy to apply to a full-color display of natural colors.

As mentioned above, the development of the organic electroluminescent element material which is stable, high in efficiency, and good in color purity is not made enough. Therefore, the development of new materials in the art continues to be required.

One embodiment of the present invention provides a novel tetrahydrophenalenoacridine-based organic compound that can be applied to an organic electroluminescent device, particularly an organic electroluminescent device.

Another embodiment of the present invention includes the tetrahydrophenalenoacridine-based organic compound to provide an organic light emitting device having improved long life, high brightness, efficiency and color purity.

Another embodiment of the present invention provides an electronic device to which the organic light emitting device is applied.

In one embodiment of the present invention, an organic compound represented by Chemical Formula 1 is provided.

<Formula 1>

Where

Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group and a substituted or unsubstituted naphthyl group. In the case where Ar1 and Ar2 are substituted, the substituent is hydrogen, deuterium (D), halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted It may include at least one selected from the group consisting of a ring C3 ~ C10 cycloalkyl group, substituted or unsubstituted C1 ~ C10 alkoxy group, phenyl group, pyridyl group and pyrimidyl group;

Ar 1 and Ar 2 may be bonded to each other to form C 3 to C 5 cycloalkyl to form a spiro structure in which a carbon atom bonded to Ar 1 and Ar 2 is a spiro atom;

R1, R2, R3 and R4 are each independently hydrogen; heavy hydrogen; halogen; CN; Si (CH ₃ ) ₃ ; CF ₃ ; Nitro; A substituted or unsubstituted C1-C40 alkyl group, a C5-C40 aryl group, a C4-C40 heteroaryl group, a C3-C40 cycloalkyl group, or a C3-C40 heterocycloalkyl group, wherein R1, R2, R3, and R4 are substituted The substituents are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group and substituted or unsubstituted C1-C10 alkoxy At least one selected from the group consisting of groups;

L is a single bond, a substituted or unsubstituted C5 to C40 arylene group, or a C4 to C40 heteroarylene group, and when L is substituted, the substituent is deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , At least one selected from the group consisting of a nitro, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted C1-C10 alkoxy group;

Z is absent, single bond, Si (CH ₃ ) ₂ , divalent amine group, substituted or unsubstituted C1 to C5 alkylene group, or substituted or unsubstituted C2 to C5 alkenylene group, and Z is substituted The substituent in the case where it is selected includes at least one selected from the group consisting of a C1 to C40 alkyl group, a C5 to C40 aryl group, a C4 to C40 heteroaryl group and a C3 to C40 cycloalkyl group;

When Z is absent, R5 and R6 are each independently a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C5-C40 aryl group, a substituted or Unsubstituted C6 to C40 arylalkyl group, substituted or unsubstituted C5 to C40 heteroaryl group, substituted or unsubstituted C3 to C40 cycloalkyl group or substituted or unsubstituted C3 to C40 heterocycloalkyl group, the R5 and Substituents when R6 is substituted are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted A substituted C1-C10 alkoxy group, a phenyl group unsubstituted or substituted with a C1-C10 alkyl group, a pyridyl group unsubstituted or substituted with a C1-C10 alkyl group, a pyridinyl group unsubstituted or substituted with a C1-C10 alkyl group, Naphthyl group unsubstituted or substituted with C1-C10 alkyl group, C1-C10 alkyl At least one selected from the group consisting of a substituted or unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group substituted or unsubstituted with a C1-C10 alkyl group, and an anthracenyl group unsubstituted or substituted with a C1-C10 alkyl group, and ;

When Z is present, R5 and R6 are each independently substituted with a substituted or unsubstituted C1-C40 alkylene group, a C2-C40 alkenylene group substituted with a C1-C10 alkyl group, and a C1-C10 alkyl group. C5-C40 arylene group substituted with C5-C40 arylene group, C6-C40 arylalkylene group substituted with C1-C10 alkyl group, C3-C40 heteroarylene group substituted with C1-C10 alkyl group, C3-C40 C1-C10 substituted with alkyl group of C1-C10 Or a C3 to C40 heterocycloalkylene group substituted with a C1 to C10 alkyl group, wherein the substituents when R5 and R6 are substituted are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro, substituted or unsubstituted C 1 -C 10 alkyl group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 1 -C 10 alkoxy group, phenyl group, C 1 -C 10 alkyl group substituted by C 1 -C 10 alkyl group, C 1 Pyridyl group substituted with an alkyl group of ~ C10, pyridinyl group substituted with an alkyl group of C1-C10, naphthyl substituted with an alkyl group of C1-C10 , And includes at least one selected from the dibenzo furanoid group, a dibenzo thiophenyl group and anthracenyl group substituted with an alkyl group the group consisting of C1 ~ C10 alkyl group substituted with a C1 ~ C10 alkyl group substituted with a C1 ~ C10;

The carbon atom or heteroatom of R5 or R6 is bonded to an adjacent pyrenyl structure and a linker X, and together with the nitrogen atom to which R5 or R6 is bonded and the linker X, a C1 to C40 alkyl group and a C5 to C40 aryl group And fused or condensed, 5- or 6-membered rings substituted or unsubstituted with a C5-C40 heteroaryl group,

The linker X is selected from the group consisting of N (Y1) and C (Y2) (Y3), wherein Y1, Y2 and Y3 are each independently a group consisting of a hydrogen atom, a C1-C10 alkyl group and a C5-C10 aryl group Is selected from,

The hetero atom; Or heteroatoms included in the heteroaryl, the heteroalkyl, the heteroarylene, and the heteroalkylene include at least one selected from the group consisting of N, O, S, Se, and Si.

In another embodiment of the present invention, an organic electroluminescent device in which an organic thin film layer composed of one or more layers including at least a light emitting layer is sandwiched between a cathode and an anode,

At least one or more layers of the organic thin film layers provide an organic electroluminescent device containing the organic compound alone or in combination of two or more thereof.

In another embodiment of the present invention, an electronic device including the organic light emitting device is provided.

The organic electroluminescent device using the organic compound may realize high luminous efficiency, high luminous brightness, high color purity and significantly improved luminous lifetime.

1 is a 1 H-NMR measurement result of the compound [1] prepared in the Example.

2 is a DSC measurement result of Compound [1] prepared in the Example.

3 is a result of TGA measurement of compound [1] prepared in the Example.

4 is a UV absorption spectrum of Compound [1] prepared in the Example.

5 is a PL (PhotoLuminescence) graph of the compound [1] prepared in the Example.

Hereinafter, the present invention will be described in detail.

The present invention may be variously modified and may have various forms, and thus embodiments (or embodiments) will be described in detail in the text. However, this is not intended to limit the present invention to the specific form disclosed, it should be understood to include all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.

The terminology used herein is for the purpose of describing particular embodiments (or aspects, aspects, or 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 “consists” are intended to indicate that there is a feature, number, step, action, component, part, or combination thereof described on the specification, but one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of 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. Terms such as those defined in the commonly used dictionaries should be construed as having meanings consistent with the meanings in the context of the related art and shall not be construed in ideal or excessively formal meanings unless expressly defined in this application. Do not.

In the present specification, the organic compound is a compound used in an organic light emitting device, and is not necessarily limited to a compound capable of emitting light, and its application range is not limited to an organic light emitting layer, and an organic electric field such as a charge injection layer and a charge transport layer. All layers may be used in any layer constituting the light emitting device.

In addition, the term 'organic compound' and 'optical device' are used herein in consideration of the case where the present invention is applied to both an organic light emitting device and a device for photovoltaic power generation regardless of a dictionary or customary definition. A term chosen to be inclusive.

In the present specification, when substituted with a case represented by "substituted or unsubstituted," unless otherwise defined, D, F, CF ₃ , OCH ₃ , halogen, nitrile group, nitro group, C1 ~ C40 alkyl group , C2 ~ C40 alkenyl group, C1 ~ C40 alkoxy group, C1 ~ C40 amino group, silane group, C3 ~ C40 cycloalkyl group, C3 ~ C40 heterocycloalkyl group, C6 ~ C40 aryl group and C5 ~ C40 When substituted with at least one substituent selected from the group consisting of a heteroaryl group.

In this specification, alkyl groups include both straight and branched chains, unless defined otherwise.

In one embodiment of the present invention, an organic compound represented by Chemical Formula 1 is provided.

<Formula 1>

Where

Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group and a substituted or unsubstituted naphthyl group. In the case where Ar1 and Ar2 are substituted, the substituent is hydrogen, deuterium (D), halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted It may include at least one selected from the group consisting of a ring C3 ~ C10 cycloalkyl group, substituted or unsubstituted C1 ~ C10 alkoxy group, phenyl group, pyridyl group and pyrimidyl group;

Ar 1 and Ar 2 may be bonded to each other to form C 3 to C 5 cycloalkyl to form a spiro structure in which a carbon atom bonded to Ar 1 and Ar 2 is a spiro atom;

R1, R2, R3 and R4 are each independently hydrogen; heavy hydrogen; halogen; CN; Si (CH ₃ ) ₃ ; CF ₃ ; Nitro; A substituted or unsubstituted C1-C40 alkyl group, a C5-C40 aryl group, a C4-C40 heteroaryl group, a C3-C40 cycloalkyl group, or a C3-C40 heterocycloalkyl group, wherein R1, R2, R3, and R4 are substituted The substituents are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group and substituted or unsubstituted C1-C10 alkoxy At least one selected from the group consisting of groups;

L is a single bond, a substituted or unsubstituted C5 to C40 arylene group, or a C4 to C40 heteroarylene group, and when L is substituted, the substituent is deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , At least one selected from the group consisting of a nitro, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted C1-C10 alkoxy group;

Z is absent, a single bond, Si (CH _{3) 2,} a bivalent amine group, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted alkenylene group of the unsubstituted C2 ~ C5 of C1~C5 ring, wherein Z is a substituted The substituent in the case where it is selected includes at least one selected from the group consisting of a C1 to C40 alkyl group, a C5 to C40 aryl group, a C4 to C40 heteroaryl group and a C3 to C40 cycloalkyl group;

When Z is absent, R5 and R6 are each independently a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C5-C40 aryl group, a substituted or Unsubstituted C6 to C40 arylalkyl group, substituted or unsubstituted C5 to C40 heteroaryl group, substituted or unsubstituted C3 to C40 cycloalkyl group or substituted or unsubstituted C3 to C40 heterocycloalkyl group, the R5 and Substituents when R6 is substituted are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted A substituted C1-C10 alkoxy group, a phenyl group unsubstituted or substituted with a C1-C10 alkyl group, a pyridyl group unsubstituted or substituted with a C1-C10 alkyl group, a pyridinyl group unsubstituted or substituted with a C1-C10 alkyl group, Naphthyl group unsubstituted or substituted with C1-C10 alkyl group, C1-C10 alkyl At least one selected from the group consisting of a substituted or unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group substituted or unsubstituted with a C1-C10 alkyl group, and an anthracenyl group unsubstituted or substituted with a C1-C10 alkyl group, and ;

When Z is present, R5 and R6 are each independently substituted with a substituted or unsubstituted C1-C40 alkylene group, a C2-C40 alkenylene group substituted with a C1-C10 alkyl group, and a C1-C10 alkyl group. C5-C40 arylene group substituted with C5-C40 arylene group, C6-C40 arylalkylene group substituted with C1-C10 alkyl group, C3-C40 heteroarylene group substituted with C1-C10 alkyl group, C3-C40 C1-C10 substituted with alkyl group of C1-C10 Or a C3 to C40 heterocycloalkylene group substituted with a C1 to C10 alkyl group, wherein the substituents when R5 and R6 are substituted are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF _3, nitro, unsubstituted or substituted with C1 ~ C10 alkyl group, a substituted or unsubstituted C3 ~ substituted by C10 cycloalkyl group, an alkyl group of a substituted or unsubstituted C1 ~ C10 alkoxy group, a phenyl group, C1 ~ C10 phenyl groups, C1 Pyridyl group substituted with an alkyl group of ~ C10, pyridinyl group substituted with an alkyl group of C1-C10, naphthyl substituted with an alkyl group of C1-C10 , And includes at least one selected from the dibenzo furanoid group, a dibenzo thiophenyl group and anthracenyl group substituted with an alkyl group the group consisting of C1 ~ C10 alkyl group substituted with a C1 ~ C10 alkyl group substituted with a C1 ~ C10;

The carbon atom or heteroatom of R5 or R6 is bonded to an adjacent pyrenyl structure and a linker X, and together with the nitrogen atom to which R5 or R6 is bonded and the linker X, a C1 to C40 alkyl group and a C5 to C40 aryl group And fused or condensed, 5- or 6-membered rings substituted or unsubstituted with a C5-C40 heteroaryl group,

The linker X is selected from the group consisting of N (Y1) and C (Y2) (Y3), wherein Y1, Y2 and Y3 are each independently a group consisting of a hydrogen atom, a C1-C10 alkyl group and a C5-C10 aryl group Is selected from,

The hetero atom; Or heteroatoms included in the heteroaryl, the heteroalkyl, the heteroarylene, and the heteroalkylene include at least one selected from the group consisting of N, O, S, Se, and Si.

The organic compound represented by Chemical Formula 1 may be used in an organic electroluminescent device to implement an organic electroluminescent device having characteristics of excellent luminous efficiency, luminescence brightness, color purity, and luminescence lifetime, or used in a photovoltaic device for solar power generation. It can be used as a photo compound.

The organic compound represented by Chemical Formula 1 may be used for various organic film layers 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. of an organic light emitting diode. As a viable material, it has improved performance, such as increased efficiency and reduced driving voltage, and maximized ability as an OLED material.

According to one embodiment, in the organic compound represented by Formula 1,

R 1 represents a hydrogen atom, a C 1 to C 10 alkyl group, a C 3 to C 10 cycloalkyl group,

Selected from the group consisting of

X ¹ is selected from the group consisting of N (Y 1) and C (Y 2) (Y 3), wherein Y 1, Y 2 and Y 3 are each independently a group consisting of a hydrogen atom, a C 1 -C 10 alkyl group and a C 5 -C 10 aryl group Is selected from;

R7 and R8 are each independently hydrogen, deuterium, halogen, CN, CF ₃ , nitro, C1-C20 straight or branched chain alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-C10 alkoxy, amino , C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10 alkyl) silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl, and C3-C10 heterocycloalkyl, n and m are integers of 1-5;

R2, R3, and R4 are each independently hydrogen or a substituted or unsubstituted C1-C10 alkyl group;

Z is absent, and R5 and R6 are each independently a hydrogen atom, a C1-C10 alkyl group,

It may be selected from the group consisting of,

X ¹ is selected from the group consisting of O, S, N (Y 1) and C (Y 2) (Y 3), wherein Y 1, Y 2 and Y 3 are each independently a hydrogen atom, a C 1 -C 10 alkyl group, and C 5 -C 10 Selected from the group consisting of aryl groups,

R ^a and R ^b are each independently hydrogen, deuterium, halogen, CN, -OH, CF ₃ , nitro, C1-C20 linear or branched alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-C10 alkoxy, amino, C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10) C10 alkyl) silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl, and C3-C10 heterocycloalkyl, k and l are 1 An integer from to 4;

Or, the R5, Z, R6 and the nitrogen atom to which they are bonded

It can form a fused ring selected from the group consisting of,

X ¹ is O, S, N, Se, Si (alkyl of C1 ~ C10) ₂ , N (Y1), C (Y2) (Y3), C (Y2) (Y3) -C (Y2) (Y3) , C (Y2) = C (Y3) and Si (Y2) (Y3), wherein Y1, Y2, and Y3 are each independently a hydrogen atom, a C1-C10 alkyl group, or a C5-C10 aryl A group, a C5 to C10 heteroaryl group, a C3 to C10 cycloalkyl group, and a C3 to C10 heterocycloalkyl group, or Y2 and Y3 are bonded to a group adjacent to each other to form a C5 to C10 aryl group, C5 to C10 Heteroaryl group, C3 to C10 cycloalkyl group or C3 to C10 heterocycloalkyl group can be formed,

P is CH ₂ or a carbon atom unsubstituted or substituted with one or two C1 to C10 alkyl groups,

R ^a and R ^b are each independently hydrogen, deuterium, halogen, CN, -OH, CF ₃ , nitro, C1-C20 linear or branched alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-- C10 alkoxy, amino, C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10 alkyl ) Silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl and C3-C10 heterocycloalkyl, k and | An integer;

Alternatively, when Z is absent and a carbon atom or a heteroatom of R 5 or R 6 is bonded to an adjacent pyrenyl structure through linker X, R 5, R 6 and linker X may be fused or Organic compounds characterized by being able to form condensed rings:

<Formula 2>

Where

X and R ^a are as defined above,

R9 is a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C2 to C40 alkenyl group, a substituted or unsubstituted C5 to C40 aryl group, a substituted or unsubstituted C6 to C40 arylalkyl group, a substituted or unsubstituted A C5 to C40 heteroaryl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, or a substituted or unsubstituted C3 to C40 heterocycloalkyl group,

The two bonding positions are linked to two adjacent carbons in the pyrenyl structure of Formula 1 to form a fused or condensed six-membered ring.

According to another embodiment, in the organic compound represented by Formula 1,

Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group and a substituted or unsubstituted naphthyl group, and when Ar1 and Ar2 are substituted Substituent of is at least one selected from the group consisting of deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group and a phenyl group May comprise;

R 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted C 3 A cycloalkyl group of -C10, wherein the substituent when R1 is substituted is deuterium or Si (CH ₃ ) ₃ ;

R <2>, R <3>, R <4> is respectively independently hydrogen or a C1-C10 alkyl group;

L is a single bond or a phenylene group;

Or, the R5, Z, R6 and the nitrogen atom to which they are bonded

It can form a fused ring selected from the group consisting of,

X ¹ is O, S, N, Se, Si (alkyl of C1 ~ C10) ₂ , N (Y1), C (Y2) (Y3), C (Y2) (Y3) -C (Y2) (Y3) , And Si (Y2) (Y3), wherein Y1, Y2, and Y3 are each independently selected from the group consisting of a hydrogen atom, a C1-C10 alkyl group, and a phenyl group,

P is CH ₂ or a carbon atom unsubstituted or substituted with one or two C1 to C10 alkyl groups,

Ra and Rb are each independently hydrogen or phenyl;

Alternatively, when Z is absent, and when a carbon atom or a hetero atom in R 5 or R 6 is bonded to an adjacent pyrenyl structure through a linker X, the R 5, R 6 and the linker X may be fused or Organic compounds characterized by being able to form condensed rings:

 <Formula 3>

Where

X is a carbon atom substituted or unsubstituted with one or two phenyl groups;

R10 is a phenyl group unsubstituted or substituted with a C1 to C10 alkyl group;

R ^a is hydrogen or a C1-C20 straight or branched alkyl group,

The two bonding positions are linked to two adjacent carbons in the pyrene structure of Formula 1 to form a fused or condensed six-membered ring.

The organic compound may have a chemical structure of any one of Compounds 1 to 185 shown in the following First Table.

[First vote group]

The organic compound represented by Chemical Formula 1 including Compound 1 to Compound 185 may be synthesized by using a synthesis method that is obviously predicted from or by referring to Schemes of the following Synthesis Example. For examples of more detailed synthetic routes of these compounds, see the schemes of the following synthesis examples. Compounds 1 to 185 are suitable for use in organic membranes of organic electroluminescent devices, particularly hole transport layers, hole injection layers or light emitting layers.

The organic layer may be formed by a soluble process using the organic compound represented by Chemical Formula 1.

In one embodiment, the organic compound represented by Formula 1 may be used as the emission layer material, specifically, may be used as a fluorescent blue dopant material.

The structure of the organic light emitting device is very diverse. One or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron blocking layer, an electron transport layer and an electron injection layer may be further included between the first electrode and the second electrode.

More specifically, in one embodiment of the organic light emitting device,

The organic light emitting device may have a structure consisting of a first electrode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode,

Alternatively, the organic light emitting device may have a structure consisting of a first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / second electrode,

Alternatively, the organic light emitting diode may have a structure of a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode.

In this case, at least one of the hole transport layer, the hole injection layer and the light emitting layer may include an organic compound represented by the formula (1).

The emission layer of the organic light emitting diode may include a phosphorescent or fluorescent dopant including red, green, blue or white. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm. In addition, the compound represented by Formula 1 may also be used as a fluorescent dopant in the light emitting layer.

Hereinafter, a method of manufacturing the organic light emitting display device will be described.

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. Herein, a substrate used in a conventional organic electroluminescent device is used, but a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used as the material for the first electrode.

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

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 ^-5 to 10 ^-3 torr, a deposition rate of 0.01 to 100 Pa / sec, and a film thickness are appropriately selected in the range of usually 100 Pa to 1 µm.

In the case of forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is about 2000 rpm to 5000 rpm. After the coating, the heat treatment temperature for removing the solvent is preferably selected from a temperature range of about 80 ° C to 200 ° C.

The hole injection layer material may be a compound represented by Chemical Formula 1.

Or phthalocyanine compounds such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or the starburst type amine derivatives described in Advanced Material, 6, p.677 (1994), for example, TCTA, m-MTDATA, m-. MTDAPB, 2-TNATA (4,4 ', 4 "-tris (N- (2-naphtyl) -N-phenylamino) triphenylamine: 4,4,4-tris (N- (naphthyl) -N-phenylamino) Triphenylamine), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): Poly (Soluble conductive polymer) 3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphor sulfonicacid: polyaniline / camphorsulfonic acid) or PANI / PSS

Known hole injection materials such as (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)) and the like can be used.

The hole injection layer may have a thickness of about 100 kPa to 10000 kPa, preferably 100 kPa to 1000 kPa. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.

Alternatively, the hole injection layer may be formed by vacuum vapor deposition. Although specific deposition conditions depend on the compound used, they are selected from the range of conditions substantially the same as the formation of a general hole injection layer. For example, DNTPD (N, N-bis- [4- (di-m-tolylamino) phenyl] -N, N-diphenylbiphenyl-4,4-diamine) may be used.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. When the hole transport layer is formed by the vacuum deposition method or the spinning method, the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from a range of conditions almost the same as that of the formation of the hole injection layer.

The hole transport layer material may include a compound represented by Formula 1 as described above. Or, for example, carbazole derivatives, such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'- diphenyl- [1,1-biphenyl] Conventional amine derivatives having aromatic condensed rings such as -4,4'-diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (? -NPD), and the like The same well-known hole transport material may be used. The hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. This is because when the thickness of the hole transport layer is less than 50 kV, hole transport characteristics may be degraded, and when the thickness of the hole transport layer exceeds 1000 kW, the driving voltage may increase.

Next, the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like. When the light emitting layer is formed by the vacuum deposition method or the spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The light emitting layer may include the compound represented by Chemical Formula 1 as described above. In this case, the compound represented by Formula 1 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 (1) independently. For host materials, for example, Alq3 (tris (8-hydroxy-quinolatealuminium) or CBP (4,4'-N, N'-dicarbazole-biphenyl), or PVK (poly (n-vinylcarbazole) ) Can be used.

In the case of the dopant material, as the fluorescent dopant, IDE102, IDE105, and C545T available from Hayashibara, Inc., which are available from Idemitsu, can be used, and red phosphorescent dopants PtOEP, RD61 of UDC, and green phosphorescent dopant Ir can be used. (PPy) 3 (PPy = 2-phenylpyridine), F2Irpic which is a blue phosphorescent dopant, red phosphorescent dopant RD 61 by UDC, etc. can be used. MQD (N-methylquinacridone), coumarin (Coumarine) derivative, etc. can also be used.

Doping concentration is not particularly limited, but the content of the dopant is generally 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 kPa to 1000 kPa, preferably 200 kPa to 600 kPa.

This is because, when the thickness of the light emitting layer is less than 100 kW, the light emission characteristics may be reduced, and when the thickness of the light emitting layer exceeds 1000 kW, the driving voltage may increase.

In the light emitting layer, when the light emitting compound is used together with the phosphorescent dopant, a method such as vacuum deposition, spin coating, cast method, LB method, or the like is applied on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer. The hole blocking layer HBL may be formed. In the case of forming the hole blocking layer by vacuum deposition or spin coating, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of forming the hole injection layer. Known hole blocking materials that can be used include, for example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and BCP.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated. When the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase. The hole blocking layer may be omitted.

Next, the electron transport layer (ETL) is formed using various methods such as vacuum deposition, spin coating, and casting.

When the electron transport layer is formed by the vacuum deposition method or the spin coating method, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer. The electron transport layer material functions to stably transport electrons injected from an electron injection electrode (Cathode), and a quinoline derivative, particularly tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, PBD and the like are known. Materials may also be used.

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. This is because when the thickness of the electron transport layer is less than 100 kV, the electron transport characteristic may be degraded, and when the thickness of the electron transport layer exceeds 1000 kW, the driving voltage may increase.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, which does not particularly limit the material.

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 the range of conditions almost the same as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 kPa to 100 kPa, preferably 5 kPa to 50 kPa. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.

Finally, the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method.

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, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Can be mentioned. In addition, a transmissive cathode using ITO and IZO may be used to obtain the front light emitting device.

Hereinafter, although a reaction example and a comparative example are illustrated concretely, this invention is not limited to the following synthesis example and an Example. In the following reaction, the intermediate compound is indicated by adding a 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. In the present specification, the chemical number is indicated as the chemical formula number. For example, the compound represented by the formula (1) is represented by compound 1.

[Reaction Example 1] Synthesis of Compound [1]

Preparation of Intermediate Compound [1-2]

In a 500 mL reaction flask, 30.0 g (83.3 mmol) of 1,6-dibromopyrene, 10.0 g (83.3 mmol) of compound [1-1], 15.9 g (83.3 mmol) of copper iodide (CuI), and potassium carbonate 25.3 150 mL of diphenyl ether was added to g (183.3 mmol), and the mixture was heated and stirred at 180 ° C. for 33 hours. After completion of the reaction, the temperature was lowered to room temperature, 200 mL of methanol was added thereto, followed by stirring and filtration under reduced pressure. Then, 150 mL of acetone and 500 mL of distilled water were added thereto, followed by stirring, followed by filtration under reduced pressure. The solid was separated and purified through silica gel chromatography to obtain 3.2 g (8%) of an intermediate compound [1-2] as a light yellow solid.

Preparation of Intermediate Compound [1-4]

In a 500 mL reaction flask, 3.2 g (6.7 mmol) of compound [1-2] was dissolved in 30 mL of tetrahydrofuran in a nitrogen atmosphere, and 6.7 mL (6.7 mmol) of compound [1-3] (1.0 M in THF) was slowly added dropwise at room temperature. It was. After stirring for 13 hours, 100 mL of aqueous NH ₄ Cl solution was added to terminate 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 purified by silica gel chromatography to give a light yellow solid. 1.1 g (29%) of an intermediate compound [1-4] were obtained.

Preparation of Intermediate Compound [1-5]

In a 500 mL reaction flask, 1.1 g (1.9 mmol) of Compound [1-4] was dissolved in 10 mL of toluene in a nitrogen atmosphere, 20 g of polyphosphoric acid was added and stirred, and 0.4 g (3.9 mmol) of methanesulfonic acid was added dropwise. After the completion of the reaction, tetrahydrofuran and methanol were added to 70 mL each, stirred for 1 hour, extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. 0.4g (38%) of solid intermediate compound [1-5] was obtained.

Preparation of Intermediate Compound [1-7]

In a 250 mL reaction flask, 0.4 g (0.7 mmol) of compound [1-5], 0.5 g (2.2 mmol) of compound [1-6], 0.1 g (0.4 mmol) of copper iodide (CuI), and 0.2 g of potassium carbonate ( 1.5 mmol) was added 50 mL of diphenyl ether and stirred at 180 ° C. for 18 hours. After completion of the reaction, 100 mL of methanol was added thereto, stirred, and filtered under reduced pressure. Then, 50 mL of acetone and 200 mL of distilled water were added thereto, followed by stirring. The solid was separated and purified through silica gel chromatography to obtain 0.3 g (57%) of the intermediate compound [1-7] as a light yellow solid.

Preparation of Compound [1]

In a 100 mL reaction flask, 2.6 g (4.2 mmol) of compound [1-7], 0.8 g (4.7 mmol) of compound [1-8], 0.8 g (8.5 mmol) of sodium tert-butoxide, and tris (dibenzylideneacetone) dipalladium (0) 0.2 50 mL of toluene was put into g (0.2 mmol) and 0.1 g (0.4 mmol) of tributylbutyl phosphines, and it stirred at reflux for 3 hours. After completion of the reaction extracted with dichloromethane and dried by filtration over anhydrous magnesium sulfate, the filtrate to give the compound [1] 1.3g (45%) of a yellow solid was purified by separation after concentration under reduced pressure, purified by silica gel chromatography.

¹ H NMR (300 MHz, THF-d ₈ ): δ 8.27 (d, 1H), 8.19 (d, 1H), 8.10 (d, 1H), 8.01-7.98 (q, 2H), 7.88 (s, 1H) , 7.85-7.81 (q, 2H), 7.48-7.46 (t, 1H), 7.21-7.20 (t, 5H), 7.19-7.09 (m, 6H), 7.07 (d, 4H), 6.95-6.63 (m, 6H), 6.91 ~ 6.90 (d, 1H), 6.75 ~ 6.73 (t, 2H), 6.60 ~ 6.58 (t, 3H)

MS / FAB: 701 (M ⁺ )

1 is a result of 1 H-NMR measurement of the compound [1] prepared above.

2 is a DSC measurement result of Compound [1] prepared above.

3 is a result of TGA measurement of Compound [1] prepared above.

4 is a UV absorption spectrum of the compound [1] prepared above.

5 is a PL (PhotoLuminescence) graph of the compound [1] prepared above.

[Reaction Example 2] Synthesis of Compound [158]

Preparation of Intermediate Compound [158-1]

In a 500 mL reaction flask, 30.0 g (83.3 mmol) of 2,7-dibromopyrene, 10.0 g (83.3 mmol) of compound [1-1], 15.9 g (83.3 mmol) of copper iodide (CuI), and potassium carbonate 25.3 100 mL of diphenyl ether was added to g (183.3 mmol), and the mixture was heated and stirred at 180 ° C. for 30 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, 300 mL of methanol was added thereto, stirred, and filtered under reduced pressure. Then, 250 mL of acetone and 500 mL of distilled water were added thereto, followed by stirring. The solid was separated and purified through silica gel chromatography to obtain 5.6 g (14%) of the intermediate compound [158-1] as a light yellow solid.

Preparation of Intermediate Compound [158-2]

In a 500 mL reaction flask, 5.6 g (11.7 mmol) of compound [158-1] was dissolved in 50 mL of tetrahydrofuran in a nitrogen atmosphere, and 11.7 mL (11.7 mmol) of compound [1-3] (1.0 M in THF) was slowly added dropwise at room temperature. It was. After stirring for 15 hours, 150 mL of NH ₄ Cl aqueous solution was added to terminate 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 purified by silica gel chromatography to give a light yellow solid. 2.4 g (37%) of an intermediate compound of [158-2] were obtained.

Preparation of Intermediate Compound [158-3]

In a 500 mL reaction flask, 2.4 g (4.3 mmol) of compound [158-2] was dissolved in 30 mL of toluene in a nitrogen atmosphere, 30 g of polyphosphoric acid was added and stirred, and 0.8 g (8.6 mmol) of methanesulfonic acid was added dropwise. After the completion of the reaction, tetrahydrofuran and methanol were added 100 mL each, stirred for 1 hour, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure, purified by silica gel chromatography, and purified by light yellow. 1.0 g (41%) of solid intermediate compound [158-3] was obtained.

Preparation of Intermediate Compound [158-4]

In a 250 mL reaction flask, 1.0 g (1.8 mmol) of compound [158-3], 1.1 g (5.3 mmol) of compound [1-6], 0.2 g (0.9 mmol) of copper iodide (CuI), and 0.5 g of potassium carbonate ( 3.5 mmol) was added 70 mL of diphenyl ether and stirred at 180 ° C. for 14 hours. After the reaction was completed, 110 mL of methanol was added thereto, stirred, and filtered under reduced pressure. Then, 50 mL of acetone and 200 mL of distilled water were added thereto, followed by stirring. The solid was separated and purified through silica gel chromatography to obtain 0.5 g (49%) of an intermediate compound [158-4] as a light yellow solid.

Preparation of Compound [158]

5.3 g (8.7 mmol) of compound [158-4], 1.8 g (10.4 mmol) of compound [1-8], 1.7 g (17.3 mmol) of sodium tert-butoxide, Tris (dibenzylideneacetone) dipalladium (0) 0.5 in a 250 mL reaction flask To mL of toluene was added to g (0.5 mmol) and 0.2 g (0.9 mmol) of tritert butylphosphine, and the mixture was stirred under reflux for 4 hours. After completion of the reaction extracted with dichloromethane and dried by filtration over anhydrous magnesium sulfate, the filtrate to give compound [158] 3.3g (55%) of a yellow solid was purified by separation after concentration under reduced pressure, purified by silica gel chromatography.

¹ H NMR (300 MHz, THF-d ₈ ): δ 8.22 (d, 1H), 8.18 (d, 1H), 8.08 (d, 1H), 7.99 ~ 7.96 (q, 2H), 7.84 ~ 7.78 (q, 2H), 7.76 (s, 1H), 7.45 ~ 7.43 (t, 1H), 7.41 (s, 1H), 7.19 ~ 7.15 (t, 4H), 7.13 ~ 7.02 (m, 10H), 6.91 ~ 6.86 (m, 7H), 6.70 ~ 6.66 (t, 2H), 6.58 ~ 6.56 (t, 3H)

MS / FAB: 701 (M ⁺ )

Comparative Example 1

Using compound a represented by the following formula a as a fluorescent blue host, compound b represented by the following formula b as a fluorescent blue 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 device having the following structure was prepared: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a + Compound b (30 nm) / Alq 3 (30 nm) / LiF (1 nm). / Al (100 nm).

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA 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. Compound a represented by Formula a and Compound b represented by Formula b (5% doping) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Thereafter, an Alq3 compound was vacuum-deposited to a thickness of 30 nm on the emission layer to form an electron transport layer. LiF 1 nm (electron injection layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transport layer to prepare an organic light emitting device as shown in [First Table Group (Group)]. This is called Comparative Sample 1.

<Formula a> <Formula b>

Examples 1-20

In Comparative Example 1, Compound 3, 7, 15, 22, 28, 35, 43, 56, 58, 88, 95, 101, 113, 117, 121 in the first table group instead of compound b as the light emitting layer fluorescent dopant compound. , ITO / 2-TNATA (80nm) / α-NPD (30nm) / [Compound] in the same manner as in Comparative Example 1 except that 133, 145, 153, 156, and 164 were used as the emission layer fluorescent blue dopant compounds, respectively. a + fluorescent blue dopant compound 3, 7, 15, 22, 28, 35, 43, 56, 58, 88, 95, 101, 113, 117, 121, 133, 145, 153, 156, 164 (5%)] An organic light emitting device having a structure of (30 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (100 nm) was manufactured. These are referred to as samples 1 to 20, respectively.

Evaluation Example 1 Evaluation of Luminescence Characteristics of Comparative Sample 1 and Samples 1 to 20

For Comparative Sample 1 and Samples 1 to 20, the luminous luminance, luminous efficiency, and luminous peak were evaluated using Keithley sourcemeter "2400" and KONIKA MINOLTA "CS-2000" based on 10 mA / cm2, respectively. It is shown in [the 2nd table | group]. The samples showed blue light emission peaks in the range of 448-461 nm.

[2nd vote group]

As shown in [Second Table], Samples 1 to 20 showed improved luminescence properties compared to Comparative Sample 1.

Evaluation Example 2 Evaluation of Life Characteristics of Comparative Sample 1 and Samples 1 to 20

For Comparative Sample 1 and Samples 1 to 20, the time at which the life span reached 97% based on 700 nits was measured using the LTS-1004AC Life Time Measuring Device of ENC technology, and the results are shown in the following [Table 3]. Viii).

 [Third vote group]

As shown in [Table 3], Samples 1 to 20 exhibited improved life characteristics compared to Comparative Sample 1.

Although the well-known techniques are omitted in the above description, those skilled in the art can easily infer, infer, and reproduce them.

Claims (13)

1. An organic compound represented by Formula 1 below:

   <Formula 1>

   

   Where

   Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group and a substituted or unsubstituted naphthyl group. In the case where Ar1 and Ar2 are substituted, the substituent is hydrogen, deuterium (D), halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro group, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted It may include at least one selected from the group consisting of a ring C3 ~ C10 cycloalkyl group, substituted or unsubstituted C1 ~ C10 alkoxy group, phenyl group, pyridyl group and pyrimidyl group;

   Ar 1 and Ar 2 may be bonded to each other to form C 3 to C 5 cycloalkyl to form a spiro structure in which a carbon atom bonded to Ar 1 and Ar 2 is a spiro atom;

   R1, R2, R3 and R4 are each independently hydrogen; heavy hydrogen; halogen; CN; Si (CH _{3) 3;} CF ₃ ; Nitro; A substituted or unsubstituted C1-C40 alkyl group, a C5-C40 aryl group, a C4-C40 heteroaryl group, a C3-C40 cycloalkyl group, or a C3-C40 heterocycloalkyl group, wherein R1, R2, R3, and R4 are substituted The substituents are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group and substituted or unsubstituted C1-C10 alkoxy At least one selected from the group consisting of groups;

   L is a single bond, a substituted or unsubstituted C5 to C40 arylene group, or a C4 to C40 heteroarylene group, and when L is substituted, the substituent is deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , At least one selected from the group consisting of a nitro, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C3-C10 cycloalkyl group, and a substituted or unsubstituted C1-C10 alkoxy group;

   Z is absent, single bond, Si (CH ₃ ) ₂ , divalent amine group, substituted or unsubstituted C1 to C5 alkylene group, or substituted or unsubstituted C2 to C5 alkenylene group, and Z is substituted The substituent in the case where it is selected includes at least one selected from the group consisting of a C1 to C40 alkyl group, a C5 to C40 aryl group, a C4 to C40 heteroaryl group and a C3 to C40 cycloalkyl group;

   When Z is absent, R5 and R6 are each independently a substituted or unsubstituted C1-C40 alkyl group, a substituted or unsubstituted C2-C40 alkenyl group, a substituted or unsubstituted C5-C40 aryl group, a substituted or Unsubstituted C6 to C40 arylalkyl group, substituted or unsubstituted C5 to C40 heteroaryl group, substituted or unsubstituted C3 to C40 cycloalkyl group or substituted or unsubstituted C3 to C40 heterocycloalkyl group, the R5 and Substituents when R6 is substituted are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro, substituted or unsubstituted C1-C10 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted A substituted C1-C10 alkoxy group, a phenyl group unsubstituted or substituted with a C1-C10 alkyl group, a pyridyl group unsubstituted or substituted with a C1-C10 alkyl group, a pyridinyl group unsubstituted or substituted with a C1-C10 alkyl group, Naphthyl group unsubstituted or substituted with C1-C10 alkyl group, C1-C10 alkyl At least one selected from the group consisting of a substituted or unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group substituted or unsubstituted with a C1-C10 alkyl group, and an anthracenyl group unsubstituted or substituted with a C1-C10 alkyl group, and ;

   When Z is present, R5 and R6 are each independently substituted with a substituted or unsubstituted C1-C40 alkylene group, a C2-C40 alkenylene group substituted with a C1-C10 alkyl group, and a C1-C10 alkyl group. C5-C40 arylene group substituted with C5-C40 arylene group, C6-C40 arylalkylene group substituted with C1-C10 alkyl group, C3-C40 heteroarylene group substituted with C1-C10 alkyl group, C3-C40 C1-C10 substituted with alkyl group of C1-C10 Or a C3 to C40 heterocycloalkylene group substituted with a C1 to C10 alkyl group, wherein the substituents when R5 and R6 are substituted are deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , nitro, substituted or unsubstituted C 1 -C 10 alkyl group, substituted or unsubstituted C 3 -C 10 cycloalkyl group, substituted or unsubstituted C 1 -C 10 alkoxy group, phenyl group, C 1 -C 10 alkyl group substituted by C 1 -C 10 alkyl group, C 1 Pyridyl group substituted with an alkyl group of ~ C10, pyridinyl group substituted with an alkyl group of C1-C10, naphthyl substituted with an alkyl group of C1-C10 , And includes at least one selected from the dibenzo furanoid group, a dibenzo thiophenyl group and anthracenyl group substituted with an alkyl group the group consisting of C1 ~ C10 alkyl group substituted with a C1 ~ C10 alkyl group substituted with a C1 ~ C10;

   The carbon atom or heteroatom of R5 or R6 is bonded to an adjacent pyrenyl structure and a linker X, and together with the nitrogen atom to which R5 or R6 is bonded and the linker X, a C1 to C40 alkyl group and a C5 to C40 aryl group And fused or condensed, 5- or 6-membered rings substituted or unsubstituted with a C5-C40 heteroaryl group,

   The linker X is selected from the group consisting of N (Y1) and C (Y2) (Y3), wherein Y1, Y2 and Y3 are each independently a group consisting of a hydrogen atom, a C1-C10 alkyl group and a C5-C10 aryl group Is selected from,

   The hetero atom; Or heteroatoms included in the heteroaryl, the heteroalkyl, the heteroarylene, and the heteroalkylene include at least one selected from the group consisting of N, O, S, Se, and Si.
2. The method of claim 1,

   R 1 represents a hydrogen atom, a C 1 to C 10 alkyl group, a C 3 to C 10 cycloalkyl group,

   

   Selected from the group consisting of

   X ¹ is selected from the group consisting of N (Y 1) and C (Y 2) (Y 3), wherein Y 1, Y 2 and Y 3 are each independently a group consisting of a hydrogen atom, a C 1 -C 10 alkyl group and a C 5 -C 10 aryl group Is selected from;

   R7 and R8 are each independently hydrogen, deuterium, halogen, CN, CF ₃ , nitro, C1-C20 straight or branched chain alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-C10 alkoxy, amino , C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10 alkyl) silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl, and C3-C10 heterocycloalkyl, n and m are integers of 1-5;

   R2, R3, and R4 are each independently hydrogen or a substituted or unsubstituted C1-C10 alkyl group;

   Z is absent, and R5 and R6 are each independently a hydrogen atom, a C1-C10 alkyl group,

   

   It may be selected from the group consisting of,

   X ¹ is selected from the group consisting of O, S, N (Y 1) and C (Y 2) (Y 3), wherein Y 1, Y 2 and Y 3 are each independently a hydrogen atom, a C 1 -C 10 alkyl group, and C 5 -C 10 Selected from the group consisting of aryl groups,

   R ^a and R ^b are each independently hydrogen, deuterium, halogen, CN, -OH, CF ₃ , nitro, C1-C20 straight or branched chain alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-C10 alkoxy, amino, C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10) C10 alkyl) silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl, and C3-C10 heterocycloalkyl, k and l are 1 An integer from to 4;

   Or, the R5, Z, R6 and the nitrogen atom to which they are bonded

   

   It can form a fused ring selected from the group consisting of,

   X ¹ is O, S, N, Se, Si (alkyl of C1 ~ C10) ₂ , N (Y1), C (Y2) (Y3), C (Y2) (Y3) -C (Y2) (Y3) , C (Y2) = C (Y3) and Si (Y2) (Y3), wherein Y1, Y2, and Y3 are each independently a hydrogen atom, a C1-C10 alkyl group, or a C5-C10 aryl A group, a C5 to C10 heteroaryl group, a C3 to C10 cycloalkyl group, and a C3 to C10 heterocycloalkyl group, or Y2 and Y3 are bonded to a group adjacent to each other to form a C5 to C10 aryl group, C5 to C10 Heteroaryl group, C3 to C10 cycloalkyl group or C3 to C10 heterocycloalkyl group can be formed,

   P is CH ₂ or a carbon atom unsubstituted or substituted with one or two C1 to C10 alkyl groups,

   R ^a and R ^b are each independently hydrogen, deuterium, halogen, CN, -OH, CF ₃ , nitro, C1-C20 linear or branched alkyl, C1-C10 haloalkyl, C1-C10 hydroxyalkyl, C1-- C10 alkoxy, amino, C1-C10 alkylamino, di (C1-C10 alkyl) amino, C5-C10 arylamino, di (C5-C10 aryl) amino, mono (C1-C10 alkyl) silyl, di (C1-C10 alkyl ) Silyl, tri (C1-C10 alkyl) silyl, C5-C10 aryl, C5-C10 heteroaryl, C3-C10 cycloalkyl and C3-C10 heterocycloalkyl, k and | An integer;

   Alternatively, when Z is absent and a carbon atom or a heteroatom of R 5 or R 6 is bonded to an adjacent pyrenyl structure through linker X, R 5, R 6 and linker X may be fused or Organic compounds characterized by being able to form condensed rings:

   <Formula 2>

   

   Where

   X and R ^a are as defined above,

   R9 is a substituted or unsubstituted C1 to C40 alkyl group, a substituted or unsubstituted C2 to C40 alkenyl group, a substituted or unsubstituted C5 to C40 aryl group, a substituted or unsubstituted C6 to C40 arylalkyl group, a substituted or unsubstituted A C5 to C40 heteroaryl group, a substituted or unsubstituted C3 to C40 cycloalkyl group, or a substituted or unsubstituted C3 to C40 heterocycloalkyl group,

   The two bonding positions are linked to two adjacent carbons in the pyrenyl structure of Formula 1 to form a fused or condensed six-membered ring.
3. The method of claim 2,

   Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group and a substituted or unsubstituted naphthyl group, and when Ar1 and Ar2 are substituted Substituent of is at least one selected from the group consisting of deuterium, halogen, CN, Si (CH ₃ ) ₃ , CF ₃ , a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C1-C10 alkoxy group and a phenyl group May comprise;

   R 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted C 3 a cycloalkyl group of ~ C10, in the case where the substituent R1 is substituted is deuterium or Si (CH _{3) 3,} and;

   R <2>, R <3>, R <4> is respectively independently hydrogen or a C1-C10 alkyl group;

   L is a single bond or a phenylene group;

   Or, the R5, Z, R6 and the nitrogen atom to which they are bonded

   

   It can form a fused ring selected from the group consisting of,

   X ¹ is O, S, N, Se, Si (alkyl of C1 ~ C10) ₂ , N (Y1), C (Y2) (Y3), C (Y2) (Y3) -C (Y2) (Y3) , And Si (Y2) (Y3), wherein Y1, Y2, and Y3 are each independently selected from the group consisting of a hydrogen atom, a C1-C10 alkyl group, and a phenyl group,

   P is CH ₂ or a carbon atom unsubstituted or substituted with one or two C1 to C10 alkyl groups,

   Ra and Rb are each independently hydrogen or phenyl;

   Alternatively, when Z is absent, and when a carbon atom or a hetero atom in R 5 or R 6 is bonded to an adjacent pyrenyl structure through a linker X, the R 5, R 6 and the linker X may be fused or Organic compounds characterized by being able to form condensed rings:

   <Formula 3>

   

   Where

   X is a carbon atom substituted or unsubstituted with one or two phenyl groups;

   R10 is a phenyl group unsubstituted or substituted with a C1 to C10 alkyl group;

   R ^a is hydrogen or a C1-C20 straight or branched alkyl group,

   The two bonding positions are linked to two adjacent carbons in the pyrene structure of Formula 1 to form a fused or condensed six-membered ring.
4. The method of claim 1,

   The organic compound is any one of the following Compounds 1 to 185.

   

   

   

   

   

   

   

   

   

   

   

   

   
5. The method of claim 1,

   The organic compound is an organic compound, characterized in that used for the use of the light emitting layer material of the organic light emitting device material.
6. The method of claim 1,

   The light emitting layer material is an organic compound, characterized in that the fluorescent blue dopant material.
7. It is an organic electroluminescent element in which the organic thin film layer which consists of one layer or multiple layers which include a light emitting layer at least is clamped between a cathode and an anode,

   An organic electroluminescent device comprising at least one organic thin film layer containing the organic compound according to any one of claims 1 to 6 alone or in combination of two or more thereof.
8. The method of claim 7, wherein

   The organic thin film layer is formed by a solution process using the organic compound

   Organic electroluminescent device.
9. The method of claim 7, wherein

   An organic light emitting display device, characterized in that the organic compound is contained as a light emitting layer material.
10. The method of claim 9,

    The light emitting layer material is an organic light emitting device, characterized in that the fluorescent blue dopant material.
11. The method of claim 7, wherein

    And an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode in this order.
12. An electronic device comprising the organic electroluminescent device according to claim 7.
13. The method of claim 12,

     The electronic device is an organic integrated circuit (O-IC), an organic field-effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC) , Organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) or organic electroluminescent devices (OLEDs)

    Electronics.

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