KR101356654B1 - Organic light emitting compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by Formula 1 and an organic light emitting device having the same:

≪ Formula 1 >

In Formula 1, Ar, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ refer to the detailed description of the invention. By using the compound, an organic light emitting device having low driving voltage, excellent efficiency, and color purity can be obtained.

Organic light emitting compound, organic light emitting device, light emitting layer

Description

Organic light emitting compound and organic light emitting device comprising the same

1A to 1C are cross-sectional views each schematically showing the structure of one embodiment of an organic light emitting device according to the present invention;

2A to 2C are views showing absorption and photoluminescence (PL) spectra in films of one embodiment of the compound according to the present invention, respectively.

3 is a view showing an emission spectrum of an organic light emitting device including one embodiment of a compound according to the present invention.

The present invention relates to an organic light emitting compound and an organic light emitting device having the same, and more particularly has excellent electrical characteristics, thermal stability and photochemical stability, and when applied to the organic light emitting device, excellent driving voltage and color purity characteristics The present invention relates to an organic light emitting device that can be represented and an organic light emitting device including the compound.

A light emitting device is a self-luminous device having a wide viewing angle, excellent contrast, and fast response time. The light emitting device includes an inorganic light emitting device using an inorganic compound for an emitting layer and an organic light emitting device (OLED) using an organic compound. The organic light emitting device has luminance, Voltage and response speed characteristics, and it is possible to make multiple colors.

The organic light emitting device generally has a stack structure of an anode / an organic light emitting layer / a cathode and includes an anode / a hole injecting layer / a hole transporting layer / a light emitting layer / an electron transporting layer / an electron injecting layer / a cathode or an anode / a hole injecting layer / a hole transporting layer / Blocking layer / electron transporting layer / electron injecting layer / cathode, and the like.

A material used for the organic light emitting device can be divided into a vacuum deposition material and a solution coating material according to a manufacturing method of an organic film. The vacuum evaporable material should have a vapor pressure of 10 ⁻⁶ torr or more under 500 ° C., and a low molecular weight material having a molecular weight of 1200 or less is preferred. The solution coatable material is highly soluble in a solvent and must be able to be prepared as a solution, and mainly includes an aromatic or heterocyclic ring.

The use of an organic electroluminescent device using a vacuum deposition method increases the manufacturing cost due to the use of a vacuum system, and it is difficult to manufacture high resolution pixels when using a shadow mask to produce pixels for color display. On the other hand, solution coating methods such as inkjet printing, screen printing, and spin coating are easy to manufacture, inexpensive to manufacture, and have a relatively higher resolution than shadow masks.

However, in the case of materials that can be used for the solution coating method, the performance of the blue light emitting molecules was inferior to the materials that can be used in the vacuum deposition method in terms of thermal stability, color purity and the like. In addition, even when the performance is excellent, after the organic film is manufactured and gradually crystallized, the crystal size may be visible light scattering by scattering the visible light corresponding to the range of the visible light wavelength, pin holes (pin hole) is formed to form There was a problem that it is easy to cause deterioration.

Japanese Patent Laid-Open No. 1999-003782 discloses anthracene substituted with two naphthyl groups as a compound that can be used in the light emitting layer or the hole injection layer. However, the compound was not satisfactory in solvent solubility and the characteristics of the organic light emitting device using the same did not reach a satisfactory level.

Therefore, there is still a need for the development of an organic electroluminescent device having improved driving voltage, brightness, efficiency, and color purity characteristics by using a blue light emitting compound which is excellent in thermal stability and capable of producing an excellent organic film.

In order to solve the problems of the prior art, the first technical problem to be achieved by the present invention is to provide an organic light emitting compound excellent in solubility and thermal stability.

The second technical problem to be achieved by the present invention is to provide an organic light emitting device having improved driving voltage, efficiency and color purity characteristics.

In order to achieve the above object of the present invention, a first aspect of the present invention provides an organic light emitting compound represented by the following formula (1):

≪ Formula 1 >

Ar in Formula 1 is a substituted or unsubstituted C ₆ -C ₅₀ aryl group;

R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are independently of each other hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C ₁ -C ₅₀ alkyl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group, substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or An unsubstituted C ₂ -C ₅₀ heteroaryl group or -N (Z ₁ ) (Z ₂ ) or -Si (Z ₃ ) (Z ₄ ) (Z ₅ ), wherein Z ₁ , Z ₂ , Z ₃ , Z ₄ and Z ₅ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, A substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group or a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group;

X is C (Z ₆ ) (Z ₇ ), N (Z ₈ ), O, S, SO ₂ , Se, or SeO ₂ , wherein Z ₆ , Z ₇ and Z ₈ are independently of each other, hydrogen, substituted or Unsubstituted C ₁ -C ₅₀ alkyl group or substituted or unsubstituted C ₆ -C ₅₀ aryl group;

However, in the above, the case where R ₂ is an anthracene group is excluded.

In order to achieve another object of the present invention, a second aspect of the present invention, the first electrode; A second electrode; And an organic light emitting device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film includes an organic light emitting compound as described above.

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

An organic light emitting compound according to the present invention is represented by the following general formula (1):

≪ Formula 1 >

In Formula 1, Ar is a substituted or unsubstituted C ₆ -C ₅₀ aryl group;

R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are independently of each other hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C ₁ -C ₅₀ alkyl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group, substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or An unsubstituted C ₂ -C ₅₀ heteroaryl group or -N (Z ₁ ) (Z ₂ ) or -Si (Z ₃ ) (Z ₄ ) (Z ₅ ), wherein Z ₁ , Z ₂ , Z ₃ , Z ₄ and Z ₅ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, A substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group or a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group;

X is C (Z ₆ ) (Z ₇ ), N (Z ₈ ), O, S, SO ₂ , Se, or SeO ₂ , wherein Z ₆ , Z ₇ and Z ₈ are independently of each other, hydrogen, substituted or Unsubstituted C ₁ -C ₅₀ alkyl group or substituted or unsubstituted C ₆ -C ₅₀ aryl group;

However, in the above, the case where R ₂ is an anthracene group is excluded.

In Formula 1, Ar and the heteroaryl group connected thereto serve to increase thermal stability and photochemical stability of the compound represented by Formula 1, wherein the substituents R ₁ to R ₅ are the It increases the solubility and amorphous properties of the compound represented by the formula (1) serves to improve the film proccesibility (film proccesibility). The compound represented by Chemical Formula 1 is suitable as a material forming an organic film interposed between the first electrode and the second electrode of the organic light emitting device. The compound of Formula 1 is suitable for use in an organic film of an organic light emitting device, particularly a light emitting layer, a hole injection layer or a hole transport layer, and is used as a dopant material as well as a host material.

The organic light emitting compound preferably has a structure of Formula 2 or 3.

(2)

 <Formula 3>

In Formulas 2 and 3, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ independently of each other, hydrogen, halogen, cyano group, nitro group, hydroxyl group, substitution Or an unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, a substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group , Substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group or -N (Z ₁ ) (Z ₂ ) or -Si (Z ₃ ) (Z ₄ ) ( Z ₅ ), and Z ₁ , Z ₂ , Z ₃ , Z ₄ and Z ₅ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl A group, a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, or a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group;

X is C (Z ₆ ) (Z ₇ ), N (Z ₈ ), O, S, SO ₂ , Se, or SeO ₂ , wherein Z ₆ , Z ₇ and Z ₈ are independently of each other, hydrogen, substituted or Unsubstituted C ₁ -C ₅₀ alkyl group or substituted or unsubstituted C ₆ -C ₅₀ aryl group,

However, in the above, the case where R ₂ is an anthracene group is excluded.

R ₁ to R ₈ in the above formula are independently of each other, hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C ₁ -C ₅₀ alkyl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy Groups, substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl groups, substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl groups, substituted or unsubstituted C ₆ -C ₅₀ aryl groups, substituted or unsubstituted C _2- Or a C ₅₀ heteroaryl group or —N (Z ₁ ) (Z ₂ ) or —Si (Z ₃ ) (Z ₄ ) (Z ₅ ), except where R ₂ is an anthracene group. At this time, the Z ₁ , Z ₂ , Z ₃ , Z ₄ and Z ₅ are independently of each other, hydrogen, substituted or unsubstituted C ₁ -C ₅₀ alkyl group, substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted Or an unsubstituted C ₂ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, or a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group.

The aryl group is a monovalent group having an aromatic ring system, and may include two or more ring systems, and the two or more ring systems may exist in a bonded or fused form with each other. The heteroaryl group refers to a group in which at least one carbon of the aryl group is substituted with at least one selected from the group consisting of N, O, S, and P. Meanwhile, a cycloalkyl group refers to an alkyl group having a ring system, and the heterocycloalkyl group Refers to a group in which at least one carbon of the cycloalkyl group is substituted with at least one selected from the group consisting of N, O, S and P.

When the alkyl group, alkoxy group, aryl group, heteroaryl group, cycloalkyl group and heterocycloalkyl group are substituted, these substituents are -F; -Cl; -Br; -CN; -NO ₂ ; -OH; C ₁ -C ₅₀ alkyl group unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO ₂ or —OH; C ₁ -C ₅₀ alkoxy group unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO ₂ or —OH; C ₆ -C ₅₀ aryl groups unsubstituted or substituted with C ₁ -C ₅₀ alkyl groups, C ₁ -C ₅₀ alkoxy groups, —F, —Cl, —Br, —CN, —NO ₂ or —OH; Unsubstituted or C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy group, a C ₂ -C ₅₀ heteroaryl group substituted with -F, -Cl, -Br, -CN, -NO 2 or -OH; Unsubstituted or C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or a C ₅ -C ₅₀ cycloalkyl group substituted with -OH; Unsubstituted or substituted C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy, -F, -Cl, -Br, -CN, -NO ₂ or -OH substituted C ₅ -C ₅₀ heterocycloalkyl and -N (Z ₉ ) may be one or more selected from the group consisting of (Z ₁₀ ). In this case, Z ₉ and Z ₁₀ are each independently hydrogen; A C ₁ -C ₅₀ alkyl group; Or a C ₆ -C ₅₀ aryl group substituted with a C ₁ -C ₅₀ alkyl group.

More specifically, R ₁ to R ₈ are each independently hydrogen, C ₁ -C ₅₀ alkyl group, C ₁ -C ₅₀ alkoxy group, phenyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group, biphenylenyl group , Anthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group, fluorenyl group, methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, ethyl-Cree Cenyl group, pisenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentaxenyl group, tetraphenylenyl group, hexaphenyl group, hexasenyl group, rubisenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group , Heptasenyl group, fluorenyl group, pyrantrenyl group, obarenyl group, carbazolyl group, thiophenyl group, indolyl group, furinyl group, benzimidazolyl group, quinolinyl group, benzothiophenyl group, parathiazinyl group, pyrrole Diary, pyrazolyl, imidazolyl, imidazolinyl, oxazolyl, thia Aryl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyridinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thianthrenyl group (thianthrenyl), cyclopentyl group, cyclohexyl group, oxiranyl group , Pyrrolidinyl group, pyrazolidinyl group, imida zolidinyl group, piperidinyl group, piperazinyl group, morpholinyl group, di (C ₆ -C ₅₀ aryl) amino group, tri (C ₆ -C ₅₀ aryl) Silyl groups and derivatives thereof.

In the present specification, the term "derivative" refers to a group in which at least one hydrogen of the groups listed above is substituted with a substituent as described above.

Of these, preferred are methyl, methoxy, phenyl, tolyl, naphthyl, pyrenyl, phenanthrenyl, fluorenyl, imidazolinyl, indolyl, quinolinyl, diphenylamino, -Tolylaminophenyl group and triphenylsilyl group are preferable.

X is C (Z ₆ ) (Z ₇ ), N (Z ₈ ), O, S, SO ₂ , Se, or SeO ₂ , wherein Z ₆ , Z ₇ and Z ₈ are independently of each other, hydrogen, substituted or Unsubstituted C ₁ -C ₅₀ alkyl group, or substituted or unsubstituted C ₆ -C ₅₀ aryl group. X is preferably CH ₂ , C (CH ₃ ) ₂ , C (C ₆ H ₅ ) ₂ , N-CH ₃ , N- (C ₆ H ₅ ) ₂ , O, S or SO ₂ .

In more detail, according to an embodiment of the present invention, the organic light emitting compound of the present invention may have a structure of Formula 4 to 100, but is not limited thereto:

<Formula 4> <Formula 5>

<Formula 6> <Formula 7>

<Formula 8> <Formula 9>

<Formula 10> <Formula 11>

<화학식 12>

&Lt; Formula 12 >

<Formula 13> <Formula 14>

<Formula 15> <Formula 16>

<Formula 17> <Formula 18>

<Formula 19> <Formula 20>

<Formula 21> <Formula 22>

<Formula 23> <Formula 24>

<Formula 25> <Formula 26>

&Lt; Formula 27 >

(28)

<Formula 29> <Formula 30>

<Formula 31> <Formula 32>

<Formula 33> <Formula 34>

<Formula 35> <Formula 36>

<Formula 37> <Formula 38>

<화학식 39>

<Formula 39>

<Formula 40> <Formula 41>

<화학식 42>

(42)

<Formula 43> <Formula 44>

<Formula 45> <Formula 46>

<Formula 47> <Formula 48>

<Formula 49> <Formula 50>

<Formula 51> <Formula 52>

<Formula 53> <Formula 54>

<Formula 55> <Formula 56>

<Formula 57> <Formula 58>

<Formula 59> <Formula 60>

<화학식 61>

<Formula 61>

<Formula 62> <Formula 63>

<화학식 64>

<Formula 64>

<Formula 65> <Formula 66>

<Formula 67> <Formula 68>

<Formula 69> <Formula 70>

<Formula 71> <Formula 72>

<Formula 73> <Formula 74>

<Formula 75> <Formula 76>

<Formula 77> <Formula 78>

<Formula 79> <Formula 80>

<Formula 81> <Formula 82>

<Formula 83> <Formula 84>

<Formula 85> <Formula 86>

<Formula 87> <Formula 88>

<Formula 89> <Formula 90>

<화학식 91>

<Formula 91>

<Formula 92> <Formula 93>

<화학식 94>

<Formula 94>

<Formula 95> <Formula 96>

<Formula 97> <Formula 98>

<Formula 99> <Formula 100>

The compound according to the present invention represented by the above formula (1) can be synthesized using a conventional synthetic method, and a more detailed synthesis route of the compound is shown in the reaction formula of the following synthesis example.

In order to achieve the second technical problem of the present invention,

A first electrode;

A second electrode; And

An organic electroluminescent device comprising an organic film interposed between the first electrode and the second electrode, wherein the organic film comprises at least one compound represented by the following formula (1):

&Lt; Formula 1 >

Wherein Ar is a substituted or unsubstituted C ₆ -C ₅₀ aryl group;

R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are independently of each other hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C ₁ -C ₅₀ alkyl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group, substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or An unsubstituted C ₂ -C ₅₀ heteroaryl group or -N (Z ₁ ) (Z ₂ ) or -Si (Z ₃ ) (Z ₄ ) (Z ₅ ), wherein Z ₁ , Z ₂ , Z ₃ , Z ₄ and Z ₅ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, A substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, or a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group;

X is C (Z ₆ ) (Z ₇ ), N (Z ₈ ), O, S, SO ₂ , Se, or SeO ₂ , wherein Z ₆ , Z ₇ and Z ₈ are independently of each other, hydrogen, substituted or Unsubstituted C ₁ -C ₅₀ alkyl group or substituted or unsubstituted C ₁ -C ₅₀ aryl group;

However, in the above, the case where R ₂ is an anthracene group is excluded.

The compound of Formula 1 is suitable for use in an organic film, particularly a light emitting layer, a hole injection layer or a hole transport layer of the organic light emitting device.

The organic electroluminescent device according to the present invention is an organic light emitting compound capable of forming a stable organic film with excellent solubility and thermal stability, unlike the conventional organic electroluminescent device having low stability of the organic film when manufactured by a solution coating method. Including the above, it is possible to provide improved light emission characteristics such as excellent driving voltage and color purity.

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, an embodiment of an organic light emitting device according to the present invention will be described with reference to Figs. 1A, 1B and 1C. The organic light emitting device of FIG. 1A has a structure of a first electrode / a hole injection layer / a light emitting layer / an electron transport layer / an electron injection layer / a second electrode, and the organic light emitting device of FIG. 1B includes a first electrode / / Light emitting layer / electron transporting layer / electron injecting layer / second electrode. 1C has a structure of a first electrode / a hole injection layer / a hole transport layer / a light emitting layer / a hole blocking layer / an electron transport layer / an electron injection layer / a second electrode. In this case, at least one of the light emitting layer, the hole injection layer and the hole transport layer may include a 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.

Hereinafter, a method of manufacturing an organic light emitting device according to the present invention will be described with reference to the organic light emitting device shown in FIG. 1C.

First, a first electrode material having a high work function on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Here, as the substrate, a substrate used in a common organic light emitting device is used, and a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and waterproofness is preferable. 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 &lt; ^-8 &gt; to 10 &lt; ^-3 &gt; torr, a deposition rate of 0.01 to 100 ANGSTROM / sec, and a film thickness of 10 ANGSTROM to 5 mu m.

When the hole injection layer is formed by the spin coating method, 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 preferably from about 2000 rpm to 5000 rpm , And the heat treatment temperature for removing the solvent after coating is suitably selected within a temperature range of about 80 캜 to 200 캜.

The hole injection layer material may be a compound having Formula 1 as described above. Alternatively, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in US Pat. No. 4,356,429, or Advanced Material, 6, p.677 (1994). The starburst amine derivatives described in TCTA, m-MTDATA, m-MTDAPB, Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly ( 3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor sulfonicacid: polyaniline / camphorsulfonic acid) Or known hole injection materials such as PANI / PSS (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)).

Pani / DBSA PEDOT / PSS

The thickness of the hole injection layer may be about 100 Å to 10000 Å, preferably 100 Å to 1000 Å. If the thickness of the hole injection layer is less than 100 angstroms, the hole injection characteristics may be degraded. If the thickness of the hole injection layer exceeds 10000 angstroms, the driving voltage may increase.

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 be a compound having Formula 1 as described above. For example, carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl ) -N, N'-diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenyl Known hole transport materials such as conventional amine derivatives having aromatic condensed rings such as benzidine (? -NPD) and the like can be used.

The thickness of the hole transporting layer may be about 50 Å to 1000 Å, preferably 100 Å to 600 Å. When the thickness of the hole transporting layer is less than 50 Å, the hole transporting property may be degraded. When the thickness of the hole transporting layer is more than 1000 Å, 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 of Formula 1 according to the present invention as described above. At this time, it may be used with a known host material suitable for the compound of formula (1), or may be used with a known dopant material. It is also possible to use the compound of Formula 1 alone. In the case of a host material, for example, Alq3 or CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole)), or the like can be used. In the case of the dopant material, as the fluorescent dopant, IDE102, IDE105, and C545T, available from Hayashibara, can be used. Ir (PPy) 3 (PPy = 2-phenylpyridine), F 2 Irpic which is a blue phosphorescent dopant, a red phosphorescent dopant RD 61 manufactured by UDC, and the like can be used. Formula (101) shows the structure of DPAVBi that can be used as a dopant.

<Formula 101>

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 Å to 1000 Å, preferably 200 Å to 600 Å. When the thickness of the light emitting layer is less than 100 Å, the light emitting characteristics may be degraded. If the thickness of the light emitting layer is more than 1000 Å, the driving voltage may increase.

When used with a phosphorescent dopant in the light emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transport layer, holes such as vacuum deposition, spin coating, cast, LB, etc. are formed on the hole transport layer. The blocking layer HBL may be formed. In the case of forming the hole blocking layer by the vacuum deposition method and the 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 which can be used, for example, oxadiazole derivatives, triazole derivatives, 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. 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.

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 functions to stably transport electrons injected from an electron injection electrode (Cathode), and a quinoline derivative, particularly a known material such as tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, etc. Can also 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 angstroms, the electron transporting characteristics may be deteriorated. When the thickness of the electron transporting layer exceeds 1000 angstroms, 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, Li2O, 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 angstrom, the electron injection characteristics may be deteriorated. If the thickness of the electron injection layer exceeds 100 angstroms, 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- . In addition, a transmissive cathode using ITO and IZO may be used to obtain the front light emitting device.

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.

Example

Synthesis Example 1

Compound 4 represented by Formula 4 was synthesized according to the reaction routes of Schemes 1, 2 and 3:

Synthesis of intermediate A

Synthesis of 9-p-tolyl-anthracene (a)

5 g (1 eq, 15.6 mmol) of 9-bromo anthracene, 3.61 g (1.7eg, 26.5 mmol) of p-tolylboronic acid, 2.15 g (1.3eq, 20.3 mmol) of Na ₂ CO _{3 in a} 500 ml round bottom flask under argon gas ), Tetrakis (triphenylphosphine) palladium (0) 0.54g (0.03eq, 0.47mmol) and 5 ml and 2.2 ml of THF and water were added per mmol of p-tolylboronic acid, respectively. Reflux. After checking that the solution turns dark brown, add water and extract with ethyl acetate. The extracted organic layer is then dried over anhydrous magnesium sulfate, filtered and the solvent is removed. The solid obtained by dissolving in a small amount of toluene and separating by column chromatography (silica, hexane) was recrystallized with toluene and methanol to obtain 4.5g (86%) of a white solid.

Synthesis of 9-bromo-10-p-tolyl-anthracene (b)

In a 500 ml round bottom flask, 4 g (1 eq, 14.9 mmol) of 9-p-tolyl-anthracene and 5.3 g (2 eq, 29.8 mmol) of NBS were dissolved in 200 ml of THF, stirred for 1 hour, and 200 ml of water was added to give yellow crystals. Got it. The resulting crystals were filtered and dissolved in a small amount of toluene, separated by column chromatography (silica, hexane) to give 4.6 g (89%) of pale yellow crystals.

Synthesis of 4,4,5,5-tetramethyl-2- (10-p-tolyl-anthracene-9-yl)-[1,3,2] -dioxaborolane (Intermediate A)

 Dissolve 4.6 g (1eq, 13.25 mmol) of 9-bromo-10-p-tolyl-anthracene in 150 ml THF in a 500 ml round-bottom flask under argon gas, and then add 6.36 ml of n-BuLi 2.5 M (hexane) at -78 ° C. 1.2eq, 15.9 mmol) is added. Then stir for 1 hour at -78 ° C and add 3.52 ml (1.3eq, 17.23 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane And stirred at room temperature for 2 hours. Then 50 ml of water is added to terminate the reaction and extracted with brine and methylene chloride. The extracted organic layer is dried over anhydrous magnesium sulfate, filtered and the solvent is removed. After dissolving in a small amount of toluene to remove impurities by column chromatography (silica, hexane) to increase the polarity of the developing solvent to obtain 3.5g (67%) of a white solid.

Synthesis of intermediate B

Synthesis of 2,3-di-p-tolyl-benzo [b] thiophene (c)

2,3-dibromo-benzo [b] thiophene (1eq, 10.27mmol), p-tolylboronic acid 4.89g (3.5eg, 35.95mmol), Na ₂ CO ₃ 2.39 in a 500 ml round bottom flask under argon gas add g (2.2eq, 22.59mmol), tetrakis (triphenylphosphine) palladium (0) 0.36g (0.03eq, 0.31mmol), and add 5ml and 2.2ml of THF and water to 1mmol of p-tolylboronic acid, respectively. Reflux at 85 ° C. for 7 hours. After the solution turns dark brown, add water and extract with ethyl acetate. The extracted organic layer is then dried over anhydrous magnesium sulfate, filtered and the solvent is removed. It was dissolved in a small amount of toluene and separated by column chromatography (silica, hexane) to obtain 2.8 g (87%) of a white solid.

Synthesis of 6-bromo-2,3-di-p-tolyl-benzo [b] thiophene (Intermediate B)

In a 500 ml round bottom flask, 2.5 g (1 eq, 7.9 mmol) of 2,3-di-p-tolyl-benzo [b] thiophene and 14 g (10 eq, 79 mmol) of NBS were dissolved in 200 ml of THF and stirred for 6 hours. 50 ml is added to terminate the reaction and extracted with brine and methylene chloride. The extracted organic layer is dried over anhydrous magnesium sulfate, filtered and the solvent is removed. The obtained solid was recrystallized from methylene chloride and hexane, dissolved in a small amount of THF and separated by column chromatography (silica, hexane) to give 2.5g (71%) of a yellow solid.

Synthesis of Compound 4

The intermediate B (2.2 mmol, 787 mg) was dissolved in 70 ml of THF, followed by 867.5 mg (2.2 mmol) of intermediate A, 231 mg (0.2 mmol) of tetrakis (triphenylphosphine) palladium (0), K ₂ CO ₃ 8 mmol Was dissolved in 30 ml of toluene and 4 ml of water, and then stirred at reflux for 24 hours. After cooling to room temperature, 100 ml of diethyl ether was added, washed twice with 100 ml of water, the organic layer was collected, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain a crude product, which was then separated by silica gel column chromatography. After purification, recrystallization. 400 mg (yield 63%) of compound 4 were obtained.

¹ H-NMR (CDCl ₃ , 300 MHz, ppm): 7.98-7.08 (m, 15H), 2.57 (s, 3H), 2.45 (s, 3H), 2.36 (s, 3H)

Synthesis Example 2

Synthesis Example 1 Synthesis Example 1 except that 6-bromo-2-phenyl-3-p-tolyl-methylindole was used instead of 2,3-dibromo-benzo [b] thiophene in the synthesis of Intermediate B. Compound 55 represented by Chemical Formula 55 was synthesized using the same method as 1.

Synthesis Example 3

Compound 7 represented by formula 7 was synthesized according to the reaction route of Scheme 4:

787 mg (2.2 mmol) of the intermediate B was dissolved in 70 ml of THF, followed by 609 mg (2.2 mmol) of 2-anthracene-9-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. ), 231 mg (0.2 mmol) of tetrakis (triphenylphosphine) palladium (0) and 8 mmol of K ₂ CO ₃ were dissolved in 30 ml of toluene and 4 ml of water, and then stirred at reflux for 24 hours. After cooling to room temperature, 100 ml of diethyl ether was added, washed twice with 100 ml of water, the organic layer was collected, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain a crude product, which was then separated and purified by silica gel column chromatography. After recrystallization, 400 mg (yield 81.5%) of compound 7 was obtained.

¹ H-NMR (CDCl ₃ , 300 MHz, ppm): 8.52-7.09 (m, 12H), 1.52 (s, 3H), 1.53 (s, 3H)

Synthesis Example 4

Compound 5 represented by formula 5 was synthesized according to the reaction route of Scheme 5:

Compound 8 was synthesized in the same manner as in Synthesis Example 1, except that 9-naphthyl-anthracene was used instead of 9-p-tolyl-anthracene when synthesizing Intermediate A in Synthesis Example 1:

¹ H-NMR (CDCl ₃ , 300 MHz, ppm): 8.02-7.15 (m, 18H), 2.47 (s, 3H), 2.38 (s, 3H)

Synthesis Example 5

Compound 17 represented by Formula 17 was synthesized according to the reaction routes of Schemes 6, 7 and 8:

Synthesis of intermediate C

Synthesis of 2,3-di-p-tolylaminophenyl-benzo [b] thiophene (d)

Synthesis of Intermediate B in Synthesis Example 1 [4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -phenyl instead of p-tolylboroonic acid 2,3-di-p-tolylaminophenyl-benzo [b] thiophene was synthesized in the same manner as in Synthesis example 1, except that] -di-p-tolylamine was used.

Synthesis of 6-bromo-2,3-di-p-tolylamiphenyl-benzo [b] thiophene (Intermediate C)

Synthesis of Intermediate B in Synthesis Example 1, except that 2,3-di-p-tolylaminophenyl-benzo [b] thiophene was used instead of 2,3-di-p-tolyl-benzo [b] thiophene. Intermediate C was synthesized using the same method as in Synthesis Example 1.

Synthesis of intermediate D

Synthesis of Intermediate A in Synthesis Example 1 using [4- (10-bromo-anthracene-9-yl-phenyl] -di-p-tolylamine instead of 9-bromo-10-p-tolyl-anthracene Intermediate D was synthesized using the same method as in Synthesis Example 1, except.

Compound 17 Synthesis

1.6 g (2.2 mmol) of the intermediate C was dissolved in 100 ml of THF, followed by 1.2 g (2.2 mmol) of the intermediate D, 231 mg (0.2 mmol) of tetrakis (triphenylphosphine) palladium (0), and 8 mmol of K ₂ CO _3. Was dissolved in 55 ml of toluene and 4 ml of water, and then stirred at reflux for 24 hours. After cooling to room temperature, 100 ml of diethyl ether was added, washed twice with 150 ml of water, the organic layer was collected, dried over anhydrous magnesium sulfate, and the solvent was evaporated to obtain a crude product, which was then separated and purified by silica gel column chromatography. After recrystallization, 843 mg (yield 68%) of compound 17 was obtained.

Evaluation Example 1-Evaluation of Thermal Stability of Compounds

The thermal stability of the compounds was evaluated by measuring the Tg (glass transition temperature) and Tm (melting point) of each compound. Tg and Tm were measured by thermal analysis using Thermo Gravimetric Analysis (TGA) and Differential Scanning Calorimetry (DSC), and the results are shown in Table 1 below:

Compound No. Tg (占 폚) Tm (占 폚) 4 247 144 5 312 146 7 212 116 17 295 149 55 273 151

Thus, it can be seen that the compound according to the present invention has a thermal stability suitable for the organic light emitting device.

Evaluation Example 2 Evaluation of Luminescent Properties of the Compound

The luminescence properties of each compound were evaluated by evaluating the UV absorption spectrum and PL (photoluminescence) spectrum of the compounds. First, Compound 4 was diluted in toluene at a concentration of 0.2 mM, and UV absorption spectra were measured using a Shimadzu UV-350 Spectrometer. This was repeated for compounds 5, 7, 17 and 55. Meanwhile, Compound 5 was diluted in toluene at a concentration of 10 mM, and PL (Photoluminecscence) spectra were measured using an ISC PC1 Spectrofluorometer equipped with a Xenon lamp. The results are shown in Table 2 below.

Compound No. Maximum absorption wavelength (nm) Maximum PL wavelength (nm) 4 378 432 5 378 440 7 368 420 17 388 457 55 375 430

Thus, it can be confirmed that the compound according to the present invention has a light emitting property suitable for application to an organic light emitting device.

Evaluation Example 3 Evaluation of Luminescence Properties of Compounds (Film State)

A film of the compound was formed to evaluate the absorption spectrum and quantum efficiency of the film.

First, a quartz substrate was prepared and washed with acetone and pure water. Thereafter, the compound was spin-coated on the substrate, and then heat-treated at a temperature of 110 ° C. for 30 minutes to form a film having a thickness of 1000 μs. The absorption spectrum and quantum efficiency of the film were measured, and the results are shown in Table 3 below. In particular, the absorption spectra of films 4, 5 and 7 are shown in Figs. 2A, 2B and 2C, respectively.

Film No. Maximum absorption wavelength (nm) Maximum PL wavelength (nm) Quantum efficiency (%) Film 4 381 438 12 Film 5 382 448 24 Film 7 374 436 19 Film 17 402 466 26 Film 55 379 435 27

Thus, when the film is formed using the compound according to the present invention, it can be seen that it has an absorption spectrum and quantum efficiency suitable for application to the organic light emitting device.

Example 1

Using the compound of Formula 101 (DPAVBi) as a dopant for the light emitting layer and using Compound 4 as a host for the light emitting layer, an organic light emitting device having the following structure was prepared: ITO / PEDOT (500 Å) / Compound 4_Dopant DPAVBi (480 Å) / Alq3 (200 Å) / LiF (10 Å) / Al (2000 Å).

The anode was cut into 50 mm x 50 mm x 0.7 mm sized 15 Ω / cm ² (1000 Å) ITO glass substrate, sonicated for 15 minutes in acetone isopropyl alcohol and pure water, followed by UV ozone cleaning for 30 minutes. Bayer's PEDOT-PSS (AI4083) was coated on the substrate and heat-treated at 110 ° C. for 5 minutes in the air and at 200 ° C. for 5 minutes in a nitrogen atmosphere to form a hole injection layer of 500 kV. Host compound 4 on the hole injection layer A mixture of 0.1 g and 0.05 g of dopant DPAVBi (the compound of Formula 101 is 5 parts by weight based on 100 parts by weight of Compound 4) was spin coated and then heat-treated at 100 ° C. for 30 minutes to form a light emitting layer having a thickness of 480 Å. . Thereafter, the Alq3 compound was vacuum-deposited to a thickness of 200 kPa on the emission layer to form an electron transport layer. LiF 10 Å (electron injection layer) and Al 2000 Å (cathode) were sequentially vacuum deposited on the electron transport layer to prepare an organic light emitting device as shown in FIG. 1A. This is called sample 1.

Example 2

In Example 1, ITO / PEDOT (500 Å) / Compound 4 (480 Å) / Alq3 (200 Å) / in the same manner as in Example 1 except that only Compound 4 was used as a light emitting layer without using a dopant as a host. An organic light emitting device having a structure of LiF (10kV) / Al (2000kV) was manufactured. This is called sample 2.

Example 3

In the same manner as in Example 1, except that Compound 7 was used instead of Compound 4 as the host, in Example 1, ITO / PEDOT (500 Å) / Compound 7_Dopant DPAVBi (480 Å) / Alq3 (200 Å) An organic light emitting device having a structure of) / LiF (10kV) / Al (2000kV) was manufactured. This is called sample 3.

Comparative Example 1

In Example 1, ITO / PEDOT (500 Å) / Compound 26_ dopant DPAVBi (480 Å) in the same manner as in Example 1, except that Compound 102 of the following formula 102 was used instead of Compound 4 as a host An organic light emitting device having a structure of / Alq 3 (200 μs) / LiF (10 μs) / Al (2000 μs) was manufactured. This is called sample 4.

<Formula 102>

Evaluation Example 4: Evaluation of Characteristics of Samples 1, 2, 3, and 4

For Samples 1, 2, 3 and Comparative Sample 4, driving voltage, color purity, and efficiency were respectively evaluated using the PR650 (Spectroscan) Source Measurement Unit. The results are shown in Table 4 below. In particular, the emission spectra of Samples 1, 2 and Comparative Sample 4 are shown in FIG. 3.

Sample No. Turn on voltage (V) CIE color coordinates
(~ 100cd / ㎡) Efficiency (cd / A) One 3.2 (0.15,0.27) 5.02 at 6.8 V 2 3.6 (0.15, 0.11) 1.60 at 6 V 3 3.4 (0.15, 0.27) 4.56 at 6.5V 4 3.4 (0.15, 0.27) 4.16Z at 5.4V

From Table 4, it can be seen that Samples 1 to 3 according to the present invention have excellent electrical properties.

Example 4

A glass substrate having an ITO transparent electrode (anode) having a thickness of 200 nm was ultrasonically cleaned for 15 minutes in neutral detergent, distilled water, acetone, and ethanol. The substrate was dried using nitrogen gas and then UV / ozone treated. The substrate was then fixed to the substrate holder of the deposition apparatus and reduced to ³ × 10 ⁻⁶ Torr for deposition. MoO 3 was deposited on the ITO substrate at a thickness of 10 nm at a deposition rate of 0.1 nm / sec to form a hole injection layer. Next, αNPD was deposited to a thickness of 30 nm at a deposition rate of 0.1 nm / sec on the hole injection layer to form a hole transport layer.

Subsequently, the compound 4 and the dopant DPAVBi were deposited simultaneously on the hole transport layer at a thickness of 20 nm at a deposition rate of 3.0 nm / sec and 0.5 nm / sec, respectively, to form a light emitting layer.

Next, Alq3 was deposited to a thickness of 20 nm at a deposition rate of 0.1 nm / sec on the emission layer to form an electron transport layer. CsCO3: BCP was co-deposited at a thickness of 20 nm at a deposition rate of 0.1 nm / sec thereon to form an electron injection layer. Aluminum was deposited as a cathode at 200 nm thickness at a deposition rate of 0.1 nm / sec to fabricate an organic light emitting device. This is called sample 5.

DC voltage was applied to the produced organic electroluminescent element, and it operated continuously at 1 mA constant current in room temperature and a drier atmosphere. Initially, blue light emission with a voltage value of 3.6 V and a luminance of 2000 cd / m 2 was confirmed. The half life of the luminance was 3500 hours.

Example 5

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound 5 instead of using the exemplary compound 4 when preparing the emission layer of Example 4. This is called Sample 6. Blue light emission was observed in the device. Furthermore, the characteristics were investigated and shown in Table 5.

Example 6

An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound 7 instead of using the exemplary compound 4 when preparing the emission layer of Example 4. Blue light emission was observed in the device. This was called sample 7. Furthermore, the characteristics were investigated and shown in Table 5.

Example 7

An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 17 was used instead of Example 4 to prepare the EML. This is called sample 8. Blue light emission was observed in the device. Furthermore, the characteristics were investigated and shown in Table 5.

Example  8

An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 55 was used instead of Example 4 to prepare the EML. This is called sample 9. Blue light emission was observed in the device. Furthermore, the characteristics were investigated and shown in Table 5.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 102 was used instead of Example 7 to prepare the EML. This is called sample 10. Blue light emission was observed in the device. Furthermore, the characteristics were investigated and shown in Table 5.

Sample No. Turn on voltage (V) CIE color coordinates
(~ 100cd / ㎡) Efficiency (cd / A @ 1000nit) 5 3.2 (0.14, 0.20) 7.58 6 3.6 (0.15, 0.22) 8.21 7 3.6 (0.14, 0.22) 7.36 8 3.4 (0.15, 0.27) 6.98 9 2.8 (0.14, 0.19) 7.15 10 4.0 (0.16, 0.29) 6.99

From Table 5, it can be seen that Samples 5 to 9 according to the present invention have excellent electrical properties.

The compound represented by Formula 1 according to the present invention not only has excellent solubility but also has excellent luminescence properties and thermal stability. Therefore, by using the compound according to the present invention, an organic light emitting device having low driving voltage and excellent color purity can be obtained.

Claims (12)

An organic light emitting compound represented by Formula 1 below: &Lt; Formula 1 >

Ar is a substituted or unsubstituted C ₆ -C ₅₀ aryl group; R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are independently of each other hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C ₁ -C ₅₀ alkyl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group, substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or An unsubstituted C ₂ -C ₅₀ heteroaryl group or -N (Z ₁ ) (Z ₂ ) or -Si (Z ₃ ) (Z ₄ ) (Z ₅ ), wherein Z ₁ , Z ₂ , Z ₃ , Z ₄ and Z ₅ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, A substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group or a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group; X is N (Z ₈ ), O, S, SO ₂ , Se, or SeO ₂ , wherein Z ₈ is hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, or a substituted or unsubstituted C ₆ -C ₅₀ Aryl group; However, except that R ₂ is an anthracene group in the above, Substituents of the said alkyl group, an alkoxy group, an aryl group, a heteroaryl group, a cycloalkyl group, and a heterocycloalkyl group are -F; -Cl; -Br; -CN; -NO ₂ ; -OH; C ₁ -C ₅₀ alkyl group unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO ₂ or —OH; C ₁ -C ₅₀ alkoxy group unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO ₂ or —OH; C ₆ -C ₅₀ aryl groups unsubstituted or substituted with C ₁ -C ₅₀ alkyl groups, C ₁ -C ₅₀ alkoxy groups, —F, —Cl, —Br, —CN, —NO ₂ or —OH; Unsubstituted or C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy group, a C ₂ -C ₅₀ heteroaryl group substituted with -F, -Cl, -Br, -CN, -NO 2 or -OH; Unsubstituted or C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or a C ₅ -C ₅₀ cycloalkyl group substituted with -OH; C ₅ -C ₅₀ heterocycloalkyl group and -N unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -F, -Cl, -Br, -CN, -NO ₂ or -OH (Z ₉ ) is one or more selected from the group consisting of (Z ₁₀ ), wherein Z ₉ and Z ₁₀ are each independently hydrogen; A C ₁ -C ₅₀ alkyl group; Or a C ₆ -C ₅₀ aryl group substituted with a C ₁ -C ₅₀ alkyl group. The organic light emitting compound of claim 1, wherein the compound is represented by the following Chemical Formula 2: (2)

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are independently of each other hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C _1- C ₅₀ alkyl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group, substituted or unsubstituted A C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, or -N (Z ₁ ) (Z ₂ ) or -Si (Z ₃ ) (Z ₄ ) (Z ₅ ), Z ₁ , Z ₂ , Z ₃ , Z ₄ and Z ₅ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, substituted or unsubstituted A substituted C ₂ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, or a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group; X is N (Z ₈ ), O, S, SO ₂ , Se, or SeO ₂ , wherein Z ₈ is hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, or a substituted or unsubstituted C ₆ -C ₅₀ Aryl group; However, except that R ₂ is an anthracene group in the above, Substituents of the said alkyl group, an alkoxy group, an aryl group, a heteroaryl group, a cycloalkyl group, and a heterocycloalkyl group are -F; -Cl; -Br; -CN; -NO ₂ ; -OH; C ₁ -C ₅₀ alkyl group unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO ₂ or —OH; C ₁ -C ₅₀ alkoxy group unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO ₂ or —OH; C ₆ -C ₅₀ aryl groups unsubstituted or substituted with C ₁ -C ₅₀ alkyl groups, C ₁ -C ₅₀ alkoxy groups, —F, —Cl, —Br, —CN, —NO ₂ or —OH; Unsubstituted or C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy group, a C ₂ -C ₅₀ heteroaryl group substituted with -F, -Cl, -Br, -CN, -NO 2 or -OH; Unsubstituted or C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or a C ₅ -C ₅₀ cycloalkyl group substituted with -OH; C ₅ -C ₅₀ heterocycloalkyl group and -N unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -F, -Cl, -Br, -CN, -NO ₂ or -OH (Z ₉ ) is one or more selected from the group consisting of (Z ₁₀ ), wherein Z ₉ and Z ₁₀ are each independently hydrogen; A C ₁ -C ₅₀ alkyl group; Or a C ₆ -C ₅₀ aryl group substituted with a C ₁ -C ₅₀ alkyl group. The organic light emitting compound of claim 1, wherein the compound is represented by the following Chemical Formula 3: <Formula 3>

Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and R ₇ are each independently hydrogen, halogen, cyano group, nitro group, hydroxyl group, substituted or unsubstituted C ₁ -C ₅₀ alkyl group, substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group, substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group, substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group or -N (Z ₁ ) (Z ₂ ) or -Si (Z ₃ ) (Z ₄ ) (Z ₅ ), Z ₁ , Z ₂ , Z ₃ , Z ₄ and Z ₅ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₆ -C ₅₀ aryl group, a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, a substituted or unsubstituted C ₅ -C ₅₀ cycloalkyl group or a substituted or unsubstituted C ₅ -C ₅₀ heterocycloalkyl group; X is N (Z ₈ ), O, S, SO ₂ , Se, or SeO ₂ , wherein Z ₈ is hydrogen, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, or a substituted or unsubstituted C ₁ -C ₅₀ Aryl group; However, except that R ₂ is an anthracene group in the above, Substituents of the said alkyl group, an alkoxy group, an aryl group, a heteroaryl group, a cycloalkyl group, and a heterocycloalkyl group are -F; -Cl; -Br; -CN; -NO ₂ ; -OH; C ₁ -C ₅₀ alkyl group unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO ₂ or —OH; C ₁ -C ₅₀ alkoxy group unsubstituted or substituted with —F, —Cl, —Br, —CN, —NO ₂ or —OH; C ₆ -C ₅₀ aryl groups unsubstituted or substituted with C ₁ -C ₅₀ alkyl groups, C ₁ -C ₅₀ alkoxy groups, —F, —Cl, —Br, —CN, —NO ₂ or —OH; Unsubstituted or C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy group, a C ₂ -C ₅₀ heteroaryl group substituted with -F, -Cl, -Br, -CN, -NO 2 or -OH; Unsubstituted or C ₁ -C ₅₀ alkyl, C ₁ -C ₅₀ alkoxy group, -F, -Cl, -Br, -CN , -NO 2 , or a C ₅ -C ₅₀ cycloalkyl group substituted with -OH; C ₅ -C ₅₀ heterocycloalkyl group and -N unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, -F, -Cl, -Br, -CN, -NO ₂ or -OH (Z ₉ ) is one or more selected from the group consisting of (Z ₁₀ ), wherein Z ₉ and Z ₁₀ are each independently hydrogen; A C ₁ -C ₅₀ alkyl group; Or a C ₆ -C ₅₀ aryl group substituted with a C ₁ -C ₅₀ alkyl group. delete The method according to any one of claims 1 to 3, wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently hydrogen, a C ₁ -C ₅₀ alkyl group. , C ₁ -C ₅₀ alkoxy group, phenyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group, biphenylenyl group, anthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group, Fluorenyl group, methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, ethyl-crisenyl group, pisenyl group, peryllenyl group, chloroperylenyl group, pentaphenyl group, pentaxenyl group , Tetraphenylenyl group, hexaphenyl group, hexasenyl group, rubisenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group, heptasenyl group, fluorenyl group, pyrantrenyl group, ovarenyl group, carbazolyl group, Thiophenyl group, indolyl group, furinyl group, benzimidazolyl group, quinolinyl group, benzothiophenyl group, parathiazinyl group, pyrroylyl group, pyrazolyl group, Imidazolyl group, imidazolinyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyridinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thianthre Thianthrenyl, cyclopentyl, cyclohexyl, oxiranyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, piperidinyl, piperazinyl, morpholinyl, di (C ₆ An organic light emitting compound, characterized in that selected from the group consisting of -C ₅₀ aryl) amino group, tri (C ₆ -C ₅₀ aryl) silyl group and derivatives thereof. The method according to any one of claims 1 to 3, wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are independently of each other methyl, methoxy, phenyl group, tol Diary, naphthyl, pyrenyl, phenanthrenyl, fluorenyl, imidazolinyl, indolyl, quinolinyl, diphenylamino, 2,3-di-p-tolylaminophenyl and triphenylsilyl and these An organic light emitting compound, characterized in that selected from the group consisting of derivatives of. The organic light emitting compound according to any one of claims 1 to 3, wherein X is N-CH ₃ , N- (C ₆ H ₅ ), O, S or SO ₂ . The organic light emitting compound according to any one of claims 1 to 3, wherein the organic light emitting compound is represented by one of the following Chemical Formulas 4 to 80:

<Formula 4> <Formula 5>

<Formula 6> <Formula 7>

<Formula 8> <Formula 9>

<Formula 10> <Formula 11>

&Lt; Formula 12 >

<Formula 13> <Formula 14>

<Formula 15> <Formula 16>

<Formula 17> <Formula 18>

<Formula 19> <Formula 20>

<Formula 21> <Formula 22>

<Formula 23> <Formula 24>

<Formula 25> <Formula 26>

<Formula 27>

<Formula 28>

<Formula 29> <Formula 30>

<Formula 31> <Formula 32>

<Formula 33> <Formula 34>

<Formula 35> <Formula 36>

<Formula 37> <Formula 38>

<Formula 39>

<Formula 40> <Formula 41>

(42)

<Formula 43> <Formula 44>

<Formula 45> <Formula 46>

<Formula 47> <Formula 48>

<Formula 49> <Formula 50>

<Formula 51> <Formula 52>

<Formula 53> <Formula 54>

<Formula 55> <Formula 56>

<Formula 57> <Formula 58>

<Formula 59> <Formula 60>

<Formula 61>

<Formula 62> <Formula 63>

<Formula 64>

<Formula 65> <Formula 66>

<Formula 67> <Formula 68>

<Formula 69> <Formula 70>

<Formula 71> <Formula 72>

<Formula 73> <Formula 74>

<Formula 75> <Formula 76>

<Formula 77> <Formula 78>

<Formula 79> <Formula 80> A first electrode; A second electrode; And an organic light emitting device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film comprises the organic light emitting compound of claim 1. The organic light emitting device of claim 9, wherein the organic layer is a light emitting layer, a hole injection layer, or a hole transport layer. The method of claim 9, further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the first electrode and the second electrode. An organic light emitting device characterized in that. The method of claim 11, wherein the device is a first electrode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode, the first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / An organic light emitting device having a structure of a second electrode or a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode.

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