KR101399636B1 - Organic light compound and organic light device using the same - Google Patents

Abstract

TECHNICAL FIELD The present invention relates to an organic light emitting compound, particularly a thiophene derivative, and an organic photonic device using the organic light emitting compound. More particularly, the present invention relates to a thiophene derivative having good charge transport properties as a phosphorescent host material and having good overlap with absorption spectrum of dopant To provide improved luminous efficiency, low voltage driving, and excellent color development rate.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic light emitting diode (OLED)

TECHNICAL FIELD The present invention relates to an organic light emitting compound, particularly a thiophene derivative, and an organic photonic device using the organic light emitting compound. More particularly, the present invention relates to a thiophene derivative having good charge transport properties as a phosphorescent host material and having good overlap with absorption spectrum of dopant To provide improved luminous efficiency, low voltage driving and excellent color development.

In 1987, Tang et al. Developed a low-molecular-weight OLED display with rapid efficiency and stability since it discovered a green luminescent phenomenon with improved efficiency and stability by forming a bilayer low-molecular organic thin film of Alq ₃ and TPD as a light emitting layer and a charge transport layer, respectively lost. In the late 1980s, the structure of a low-molecular OLED device started from a simple structure of an anode (ITO), a hole transport layer (HTL), an emission layer (EML), and a cathode (Mg: Ag). In the case of fluorescent devices, Hole Injection Layer (HIL) such as CuPc was introduced, Al: Li was developed as cathode and electron injection layer material, and materials such as LiF were developed and the structure became complicated. As a result, the efficiency and the driving voltage of the electro-optical characteristic have been improved.

The phosphorescent structure is generally composed of an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transfer layer (ETL), an electron injection layer (EIL), and a cathode Hole blocking layer (HBL) layer has been introduced as a layer but it is not necessarily a necessary layer.

The light emitting layer material is largely divided into a light emitting material for a fluorescent element and a light emitting material for a phosphorescent element, and is classified again according to a luminescent color. The light emitting layer material is divided into a host material and a dopant material. Host or Dopant materials can emit light, but their efficiency and brightness are very low due to their own quenching phenomenon. Due to self-aggregation phenomenon between molecules, Dopant is doped into the host to form a light emitting layer.

CBP, which is a bipolar material with hole mobility and electron mobility, has been widely used for phosphorescent host materials for Red and Green. Recently, however, it has been known that Balq, an electron transporting material, or a similar kind of Al complex material is useful as a phosphorescent red host. It is also known that CBP derivative and Artsi family substances have excellent properties as a material for blue phosphorescent host.

The characteristics required for the host material must first be excellent in charge transport properties. It is necessary to move the holes and electrons in the light emitting layer, so that the mobility is appropriately required. In addition, the host material must transfer the energy to the dopant, so that the emission spectrum of the host should be well overlapped with the absorption spectrum of the dopant so that the energy transfer occurs well. In terms of energy, the band gap of the host should be wider than the gap of the dopant, and the LUMO level of the host should be higher than the Dopant LUMO.

A first object of the present invention is to provide a novel organic photo-compound which can be applied to an organic photonic device, particularly an organic electroluminescent device.

A second object of the present invention is to provide an organic electroluminescent device including the novel compound and having a low driving voltage and improved luminous efficiency, brightness, color purity, thermal stability and lifetime, and an organic photonic device for solar power generation .

In particular, the present invention aims to develop a thiophene derivative having a good charge transporting property as a phosphorescent host material and having a good overlap with the absorption spectrum of the dopant to obtain improved luminous efficiency, low voltage driving, and excellent color development rate.

The organic electroluminescent compound according to the present invention and the organic photoconductor using the same are based on the organic electroluminescent compound represented by the following formula (F)

<Formula F>

In the above formula (F)

X is N, O, S, Si or Se,

a1 and a2 are dependent on X,
Each independently 0 (zero) (when X is O, S or Se, a1 and a2 are all 0) (when X is N, a1 is 0)
A2 when X is N or a1 and a2 when X is Si are each a C1-C50 alkyl group; C6-C50 aryl group, or a substituted or unsubstituted C2-C50 hetero aryl group,

A is selected from H, D, F, a C1-C50 alkyl group, a C1-C50 alkoxy group, a C1-C50 ketone group, a silyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group , A substituted or unsubstituted C2-C50 cycloalkyl group, or a substituted or unsubstituted C2-C50 heterocycloalkyl group,

R is an aromatic ring or an aliphatic ring,

B1 and B2 are each independently selected from the group consisting of H, D, F, a C1-C50 alkyl group, a C1-C50 alkoxy group, a C1-C50 ketone group, a silyl group, a substituted or unsubstituted C6- C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, or a substituted or unsubstituted C2-C50 heterocycloalkyl group,

b1 and b2 are zero when R is an aromatic ring, C1-C50 alkyl group when R is an aliphatic ring,

R1 and R2 are each independently

A substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C1-C50 alkyl group, a C1-C50 alkoxy group, a C1-C50 ketone group, Or an unsubstituted C2-C50 cycloalkyl group, or a substituted or unsubstituted C2-C50 heterocycloalkyl group

R1 and R2 together form a fused aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring together with the adjacent ring.

The organic optical compound according to the present invention and the organic optical device using the same

The formula (F) is preferably any one of the following organic luminescent compounds represented by the following formulas (F1) to (F11)

<Formula F1>

<Formula F2>

<Formula F3>

<Formula F4>

<Formula F5>

<Formula F6>

<Formula F7>

<Formula F8>

<Formula F9>

<Formula F10>

<Formula F11>

In each of the above formulas F1 to F11

A is selected from H, D, F, a C1-C50 alkyl group, a C1-C50 alkoxy group, a C1-C50 ketone group, a silyl group, a substituted or unsubstituted C6-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group , A substituted or unsubstituted C2-C50 cycloalkyl group, or a substituted or unsubstituted C2-C50 heterocycloalkyl group,

B1 and B2 are each independently selected from the group consisting of H, D, F, a C1-C50 alkyl group, a C1-C50 alkoxy group, a C1-C50 ketone group, a silyl group, a substituted or unsubstituted C6- C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, or a substituted or unsubstituted C2-C50 heterocycloalkyl group,

In Formula F1,

X1 and X2 are each C (carbon) or N,

D1 and D2 are any one of H, D and F,

In the above formula (F4 or F10)

D is a group forming an adjacent ring and a fused aromatic ring, a condensed hetero aromatic ring.

Further, the organic optical compound according to the present invention and the organic optical device using the organic optical compound are based on organic optical compounds corresponding to the following Chemical Formulas 1 to 204

The organic optical device according to the present invention provides high luminous efficiency, high luminance, high color purity and remarkably improved luminous lifetime,

In addition, the present invention provides organic light emitting devices and organic light emitting compounds, or organic photoconductors and optical compounds for solar power generation. Above all, the organic photonic device according to the present invention has an excellent charge transporting property as a phosphorescent host material, and develops a thiophene derivative having a good overlap with absorption spectrum of dopant to provide improved luminous efficiency, low voltage driving, and excellent color development rate.

Hereinafter, the present invention will be described in detail.

While the present invention has been described in connection with certain embodiments, it is obvious that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the invention. It is to be understood, however, that the invention is not intended to be limited to the particular forms disclosed, but on the contrary, is intended to cover all modifications, equivalents, and alternatives falling within the spirit and scope of the invention.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The singular expressions include plural expressions unless the context clearly dictates otherwise. In the present application, the term &quot; comprising &quot; or &quot; consisting of &quot;, or the like, refers to the presence of a feature, a number, a step, an operation, an element, a component, But do not preclude the presence or addition of one or more other features, integers, steps, operations, components, parts, or combinations thereof.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Terms such as those defined in commonly used dictionaries are to be interpreted as having a meaning consistent with the contextual meaning of the related art and are to be interpreted as either ideal or overly formal in the sense of the present application Do not.

The present invention has developed a thiophene derivative and can be used in various ways such as various organic films between a first electrode and a second electrode such as an electron transport layer (ETM), a light emitting layer (EML), a hole transport layer (HTM) And to develop a material that maximizes its performance as an OLED material, such as increased efficiency and reduced driving voltage. In particular, the thiophene derivative has excellent charge transport properties as a phosphorescent host material and develops a thiophene derivative having a good overlap with absorption spectrum of dopant to provide improved luminous efficiency, low voltage driving and excellent color development rate.

In the present specification, the term "organic photocompound" means a compound used in an organic photonic device. The scope of the present invention is not limited to the organic luminescent layer. The scope of the present invention is not limited to the organic luminescent layer. Can be used for any layer constituting the substrate.

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

An organic photonic device according to the present invention includes a first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode,

Wherein the organic film comprises an organic luminescent compound represented by the following formula (F): &lt; EMI ID =

<Formula F>

In the above formula (F)

X is N, O, S, Si or Se,

a1 and a2 are dependent on X,
Each independently 0 (zero) (when X is O, S or Se, a1 and a2 are all 0) (when X is N, a1 is 0)
A2 when X is N or a1 and a2 when X is Si are each a C1-C50 alkyl group; A substituted or unsubstituted C6-C50 aryl group, or a substituted or unsubstituted C2-C50 heteroaryl group,

A is a group selected from the group consisting of H, D, F, C1 to C50 alkyl groups, C2 to C50 alkenyl groups, C2 to C50 alkynyl groups, C1 to C50 alkoxy groups, C1 to C50 ketone groups, A substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, a C5-C50 aryloxy group, a C1- C50 alkyloxy group, C5-C50 arylamino group, C5-C50 diarylamino group, or C6-C50 arylalkyl group,

R is an aromatic ring or an aliphatic ring, especially an aromatic ring of C6 or an aliphatic ring of C6,

B1 and B2 are each independently selected from the group consisting of H, D, F, C1 to C50 alkyl groups, C2 to C50 alkenyl groups, C2 to C50 alkynyl groups, C1 to C50 alkoxy groups, C1 to C50 ketone groups, A substituted or unsubstituted C5-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, An alkyloxy group of C 1 to C 50, an arylamino group of C 5 to C 50, a diarylamino group of C 5 to C 50, or an arylalkyl group of C 6 to C 50,

b1 and b2 are zero when R is an aromatic ring, C1-C50 alkyl group when R is an aliphatic ring,

R1 and R2 are each independently

A substituted or unsubstituted C5-C50 alkyl group, a substituted or unsubstituted C5-C50 alkenyl group, a substituted or unsubstituted C5-C50 alkynyl group, a substituted or unsubstituted C5- A substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, a C5-C50 aryloxy group, a C1-C50 An alkyloxy group, an arylamino group of C5 to C50, a diarylamino group of C5 to C50, or an arylalkyl group of C6 to C50

R1 and R2 together form a fused aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring together with the adjacent ring.

Further, the above formula (F) is a compound represented by the following formula (F1) (corresponding to 1 to 63 and 177 to 197 in the following compounds 1 to 204), F2 (corresponding to 64 to 82 in the following compounds 1 to 204), F3 To 101), F4 (corresponding to 102 to 139 in the following compounds 1 to 204), F5 (corresponding to 140 to 158 in the following compounds 1 to 204), F6 (corresponding to the following compounds 1 to 204 to 159 to 163) , F7 (corresponding to the following compounds 1 to 204 correspond to 164 to 168), F8 (corresponding to the following compounds 1 to 204 to 169 to 172), F9 (corresponding to the following compounds 1 to 204 to 173 to 176), F10 1 to 204 to 198 to 203), or F11 (corresponding to the following compounds 1 to 204 to 204).

<Formula F1>

<Formula F2>

<Formula F3>

<Formula F4>

<Formula F5>

<Formula F6>

<Formula F7>

<Formula F8>

<Formula F9>

<Formula F10>

<Formula F11>

In each of the above formulas F1 to F11

A is a group selected from the group consisting of H, D, F, C1 to C50 alkyl groups, C2 to C50 alkenyl groups, C2 to C50 alkynyl groups, C1 to C50 alkoxy groups, C1 to C50 ketone groups, A substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, a C5-C50 aryloxy group, a C1- C50 alkyloxy group, C5-C50 arylamino group, C5-C50 diarylamino group, or C6-C50 arylalkyl group,

B1 and B2 are each independently selected from the group consisting of H, D, F, C1 to C50 alkyl groups, C2 to C50 alkenyl groups, C2 to C50 alkynyl groups, C1 to C50 alkoxy groups, C1 to C50 ketone groups, A substituted or unsubstituted C5-C50 aryl group, a substituted or unsubstituted C2-C50 heteroaryl group, a substituted or unsubstituted C2-C50 cycloalkyl group, a substituted or unsubstituted C2-C50 heterocycloalkyl group, An alkyloxy group of C 1 to C 50, an arylamino group of C 5 to C 50, a diarylamino group of C 5 to C 50, or an arylalkyl group of C 6 to C 50,

In Formula F1,

X1 and X2 are each C (carbon) (corresponding to 1 to 63 and 177 to 1195 in the following compounds 1 to 204) or N (corresponding to the following compounds 1 to 204 to 196 and 197)

D1 and D2 are any one of H, D and F,

In the above formula (F4 or F10)

D is a group forming an adjacent ring and a fused aromatic ring, a condensed hetero aromatic ring.

In the above formulas (F) and (F1) to (F11), the respective functional groups are commonly represented by A, B1, B2, C1, C2, D, D1 or D2.

The C 1 to C 50 alkyl group, the C 2 to C 50 alkenyl group, the C 2 to C 50 alkynyl group, the C 5 to C 50 aryl group, the C 5 to C 50 heteroaryl group, the C 5 to C 50 heteroaryl group, A C5-C50 arylamino group, a C5-C50 arylamino group, a C5-C50 diarylamino group, a C6-C50 arylalkyl group, a C3-C50 cycloalkyl group, and a C3-C50 heterocyclo The alkyl group

A C1 to C50 alkyl group, a C1 to C50 alkoxy group, a C1 to C50 amino group, a C3 to C50 cycloalkyl group, a C3 to C50 alkenyl group, a C1 to C50 alkoxy group, A C5-C50 heteroaryl group, a C5-C50 heteroaryl group, a C5-C50 heteroaryl group, and the like.

The above-mentioned C1 to C50 alkyl groups, C2 to C50 alkenyl groups, C2 to C50 alkynyl groups, C5 to C50 aryl groups, C5 to C50 heteroaryl groups, C5 to C50 heteroaryl groups, C5 to C50 aryloxy groups, C5 to C50 arylamino groups, C5 to C50 diarylamino groups, C6 to C50 arylalkyl groups, C3 to C50 cycloalkyl groups, and C3 to C50 heterocycloalkyl groups Lt; RTI ID = 0.0 &gt;

A C5-C50 aryl group, a C5-C50 aryl group, a C5-C50 aryl group, a C5-C50 aryl group, a C5-C50 heteroaryl group, The heteroaryl group of C50 is

A C1 to C50 alkyl group, a C1 to C50 alkoxy group, a C1 to C50 amino group, a C3 to C50 cycloalkyl group, a C3 to C50 alkenyl group, a C1 to C50 alkoxy group, At least one second substituent selected from the group consisting of a C5 to C50 heterocycloalkyl group, a C5 to C50 aryl group, and a C5 to C50 heteroaryl group; Or to form adjacent condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings or condensed heteroaromatic rings or spiro bonds.

Further, the above-mentioned C1 to C50 alkyl group, C2 to C50 alkenyl group, C2 to C50 alkynyl group, C5 to C50 aryl group, C5 to C50 heteroaryl group, and C5 to C50 heteroaryl groups of A, B1, B2, C5 to C50 aryloxy groups, C5 to C50 arylamino groups, C5 to C50 diarylamino groups, C6 to C50 arylalkyl groups, C3 to C50 cycloalkyl groups, and C3 to C50 heterocycloalkyl groups Lt; RTI ID = 0.0 &gt;

A phenanthryl group, a phenanthryl group, an anthracenyl group, a benzoanthracenyl group, an azranyl group, an acenaphthylenyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A phenanthryl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, A phenyl group, a hexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a fluorenyl group, a pyranthrenyl group, an obenyl group, a carbazolyl group, a dibenzofuranyl group, A thiophenyl group, a thiophenyl group, an indolyl group, a purinyl group, a benzimidazolyl group, a quinolizinyl group, a quinolinyl group, a benzothiophenyl group, a parathiazinyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, , Thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, A pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a thianthrenyl group, a cyclopentyl group, a cyclohexyl group, an oxiranyl group, a pyrrolidinyl group, a pyrazolidinyl group, (C6-C50 aryl) amino group, silyl group, and derivatives thereof are preferable.

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 condensed form to 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 member selected from the group consisting of N, O, S, P, Si and Se.

On the other hand, the 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 in the cycloalkyl group is substituted with at least one member selected from the group consisting of N, O, S, P, Si and Se .

When at least one hydrogen of said aryl group and heteroaryl group is substituted, said substituent is selected from the group consisting of a D, F, C1-C50 alkyl group; A C1-C50 alkoxy group; A C6-C50 aryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; A C2-C50 heteroaryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; A C5-C50 cycloalkyl group which is unsubstituted or substituted by a C1-C50 alkyl group or a C1-C50 alkoxy group and a C5-C50 heterocycloalkyl group which is unsubstituted or substituted by a C1-C20 alkyl group or a C1-C20 alkoxy group, &Lt; / RTI &gt;

An organic photonic device according to a first aspect of the present invention includes: a first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode.

The organic photo-compound used in the organic photonic device of the present invention may have, but is not limited to, the structures of the following formulas (1) to (204)

One

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The organic photo-compounds according to the present invention represented by the above Chemical Formulas 1 to 204 can be synthesized using conventional synthetic methods, and more detailed synthesis routes of the compounds will be described with reference to the reaction schemes of the following synthesis examples. The compound of the above formula is suitable for use in an organic film of an organic optical device, particularly a hole transporting layer, a hole injecting layer or a light emitting layer. The structure of the organic light emitting device according to the present invention is very diverse. The organic EL device may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron blocking layer, an electron transporting layer, and an electron injecting layer between the first electrode and the second electrode.

More specifically, an embodiment of an organic light emitting device according to the present invention

First, the organic light emitting device may have a structure including a first electrode / a hole injection layer / a light emitting layer / an electron transport layer / an electron injection layer / a second electrode,

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

Further, the organic light emitting device may have 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.

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

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

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

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

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

Alternatively, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or starburst amine derivatives such as TCTA, m-MTDATA, and m-MTDATA described in Advanced Material, 6, p.677 (1994) MTDAPB, 2-TNATA (4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenylamino) triphenylamine: 4,4,4- (Polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), which is a soluble conductive polymer, Styrene sulfonate), PANI / CSA (polyaniline / camphor sulfonic acid) or PANI / PSS (polyaniline / camphor sulfonic acid)

(Polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)) and the like can be used.

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.

Alternatively, the hole injection layer may be formed by a vacuum vapor deposition method. The specific deposition conditions vary depending on the compound used, but are selected from substantially the same range of conditions as the formation of a general hole injection layer. For example, 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 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 comprise a compound of the formula as described above. Or carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole and the like, N, N'-bis (3-methylphenyl) -N, N'- diphenyl- [ Amine having an aromatic condensed ring such as N, N'-tetramethyldisiloxane, -4,4'-diamine (TPD) and N, N'-di (naphthalen- The hole transporting layer may have a thickness of 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 comprise a compound of the formula according to the present invention as described above. At this time, the compounds of the formula can be used together with suitable known host materials or can be used together with known dopant materials.

It is also possible to use the compound of the above formula alone. In the case of the host material, for example, Alq3 (tris (8-hydroxy-quinolatealuminium) or CBP (4,4'-N, N'-dicarbazole- ) Can be used.

In the case of the dopant material, IDE102, IDE105 and IDE55 available from Idemitsu Co., Ltd. and C545T available from Hayashibara Co., Ltd. can be used. As the phosphorescent dopant, red phosphorescent dopant PtOEP, UDC RD61, green phosphorescent dopant Ir (PPy) 3 (PPy = 2-phenylpyridine), a blue phosphorescent dopant F2Irpic, and a red phosphorescent dopant RD 61 manufactured by UDC. MQD (N-methylquinacridone), coumarine derivatives and the like can also be used.

The doping concentration is not particularly limited, but the content of the dopant is usually 0.01 to 15 parts by weight based on 100 parts by weight of the host. The thickness of the light emitting layer may be about 100 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 a luminescent compound is used together with a phosphorescent dopant in the luminescent layer, a method such as vacuum deposition, spin coating, casting, LB or the like is performed on the luminescent layer to prevent the triplet excitons or holes from diffusing into the electron transporting layer The hole blocking layer HBL can be formed. 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. If the thickness of the hole blocking layer is less than 50 angstroms, the hole blocking characteristics may be deteriorated. If the thickness of the hole blocking layer exceeds 1000 angstroms, the driving voltage may be increased. An organic light emitting element having the structure shown in FIG. 1B is obtained.

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

In the case of forming the electron transporting layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but generally, the conditions are substantially the same as those for forming the hole injection layer. The electron transport layer material serves to stably transport electrons injected from an electron injection electrode, and is a quinoline derivative, particularly a known material such as tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, Materials may 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- . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic electroluminescent compound according to another embodiment of the present invention may be represented by the above formula, and more specifically, the organic electroluminescent compound represented by the above general formulas (1) to (204). The details of the compounds are the same as those described for the organic foot and the device described above.

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

[Reaction Example 1] Synthesis of Compound [1]

Preparation of intermediate compound [1-1]

In a 3 L reaction flask, 104.8 g (0.708 mol) of phthalic anhydride was stirred in 1 L of anhydrous dichloromethane in a nitrogen atmosphere at room temperature. 236 g (1.77 mol) of aluminum chloride are slowly added in three portions. (0.745 mol) of benzo [b] thiophene were dissolved in 300 mL of anhydrous dichloromethane and slowly dropped into the reaction solution. After stirring at room temperature for 1 hour, the reaction mixture was poured into 2 L of 1N hydrochloric acid aqueous solution and layered. The organic layer is washed with saturated brine and the organic layer is separated. The organic layer is dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and recrystallized from dichloromethane and hexane to obtain 153 g (76%) of intermediate compound [1-1].

Preparation of intermediate compound [1-2]

100.0 g (0.352 mol) of the intermediate compound [1-1] was added to the flask, and the mixture was stirred at 100 캜 for 3 hours with 1.5 L of polyphosphoric acid. The reaction solution is cooled to room temperature and poured into 3 L of purified water to solidify it. The solid was recrystallized from dichloromethane and methanol to give 58 g (62%) of yellow intermediate compound [1-2].

Preparation of intermediate compound [1-3] and compound [1]

In a flask, 8.17 g (52.01 mmol) of bromobenzene is dissolved in 100 mL of anhydrous tetrahydrofuran. At 78 ° C, 20.8 mL (52.01 mmol) of a solution of normal butyl lithium (2.5 mol) is slowly added dropwise. At the same temperature, 5.3 g (20.80 mol) of the intermediate compound [1-2] are added and the temperature is raised to room temperature for 8 hours. The reaction solution was poured into 200 mL of a saturated aqueous ammonium solution. The organic layer is separated and washed with saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The intermediate compound [1-3] obtained by concentrating the filtrate under reduced pressure is stirred with 200 mL of acetic acid. 22.0 g (0.208 mol) of sodium hypophosphite monohydrate and 17.3 g (0.104 mol) of potassium iodide were added, and the mixture was refluxed and stirred for 12 hours. Cool to room temperature and filter the resulting solid. And washed with methanol to prepare 3.0 g (37%) of the target compound [1] as a white solid.

[Reaction Example 2] Synthesis of Compound [23]

Preparation of intermediate compound [23-1]

100 g (0.352 mol) of the intermediate compound [1-1], 230 g (3.52 mol) of zinc powder and 140.8 g (3.52 mol) of sodium hydroxide were put in a 3 L flask and stirred at 150 캜 for 12 hours with 1.5 L of diethylene glycol. The reaction temperature is cooled to room temperature and then filtered through diatomaceous earth. The filtrate is acidified with a 1N aqueous hydrochloric acid solution and the solid is filtered off. Separation and purification were conducted by column chromatography to obtain 69 g (73%) of intermediate compound [23-1] as a white solid.

Preparation of intermediate compound [23-2]

69 g (0.257 mol) of the intermediate compound [23-2] are stirred in 500 ml of methanesulfonic acid at about 60 ° C for 4 hours, and then cooled to room temperature. The reaction solution is poured into 1 L of water and solidified. The brown solid was recrystallized from dichloromethane and methanol and then separated and purified by column chromatography to obtain 35 g (54%) of intermediate compound [23-2] as a white solid.

Preparation of intermediate compound [23-3]

18.4 g (59.92 mmol) of 2-bromotriphenylene, 1.45 g (59.92 mmol) of magnesium and 0.1 mL of 1,2-dibromoethane were charged into a 250 mL three-neck reaction flask and refluxed under nitrogen atmosphere for 4 hours. The reaction solution was cooled to room temperature and 5.0 g (19.97 mmol) of the intermediate compound [23-2] was added. The reaction temperature is raised and refluxed for 12 hours. After cooling to room temperature, the reaction mixture was poured into 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. The organic layer was separated and recrystallized from dichloromethane and methanol to obtain 5.5 g (60%) of an intermediate compound [23-3] as a white solid.

Preparation of intermediate compound [23-4]

5.0 g (10.85 mmol) of the intermediate compound [23-3] and 2.31 g (13.03 mmol) of N-bromosuccinimide are stirred in 100 mL of dimethylformamide for 5 hours. The reaction solution is poured into purified water to solidify. The solid was filtered and recrystallized from dichloromethane and methanol to yield 4.5 g (77%) of the intermediate compound [23-4].

Preparation of compound [23]

(8.34 mmol) of intermediate compound [23-4]], 1.72 g (10.0 mmol) of 2-naphthylboronic acid, 192 mg (0.17 mmol) of tetrakis (triphenylphosphine) palladium, (12.51 mmol) of potassium carbonate (K ₂ CO ₃ ), and the mixture was stirred under reflux for 12 hours with 100 mL of 1,4-dioxane and 10 mL of purified water under a nitrogen stream. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid was washed with purified water and methanol, and recrystallized from dichloromethane and methanol to give 3.5 g (72%) of the target compound [23] as a white solid.

[Reaction Example 3] Synthesis of compounds [83] and [84]

Preparation of intermediate compound [83-2]

50.0 g (0.166 mol) of the compound [83-1] was suspended and stirred in 1 L of isopropanol in a reaction flask. Slowly add 15.7 g (0.416 mol) of sodium borohydride at room temperature. The reaction temperature is raised to reflux and stir for 6 hours. After cooling to room temperature, it is poured very slowly into 2 L of 1N hydrochloric acid aqueous solution. The orange solid is filtered off and washed with methanol. The solid was recrystallized from dichloromethane and methanol to give 39.0 g (83%) of the intermediate compound [83-1].

Preparation of compound [83]

To the reaction flask, 39 g (0.137 mol) of the intermediate compound [83-2] was stirred with 500 mL of diglyme, and 65 g (1.715 mol) of lithium aluminum hydride was slowly added several times. Heated to 160 DEG C for 12 hours and cooled to room temperature. Slowly pour the reaction solution into 2 L of 1 N aqueous hydrochloric acid solution and filter the solid. After washing with purified water, recrystallization from dichloromethane and methanol gave 25 g (53%) of the target compound [83] as a white solid.

Preparation of intermediate compound [84-1]

20.0 g (58.39 mmol) of the compound [83] are stirred in 500 ml of anhydrous tetrahydrofuran, and 28.0 ml (70.07 mmol) of 2.5 mol-butyl lithium at 0 ° C is slowly added dropwise to the flask. 7.81 mL (70.07 mmol) of trimethyl borate is slowly added dropwise at the same temperature. The reaction mixture was gradually warmed to room temperature for 10 hours, and the reaction solution was poured into 1 L of a saturated aqueous ammonium solution to separate the layers. The organic layer is separated and washed with 1 L of saturated brine. The organic layer is separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and recrystallized from dichloromethane and normal-hexane to obtain 13 g (58%) of intermediate compound [84-1] as a white solid.

Preparation of compound [84]

(11.67 mmol) of 9-bromophenanthrene, 5.4 g (14.0 mmol) of intermediate compound [84-1], 270 mg (0.233 mmol) of tetrakis (triphenylphosphine) palladium, 10 mL of an aqueous sodium carbonate solution and 100 mL of 1,4-dioxane were added, followed by reflux stirring in a nitrogen atmosphere for 10 hours. Methanol is added at room temperature to crystallize. The solid was filtered and recrystallized from dichloromethane and methanol to give 3.7 g (61%) of the desired compound as an off-white solid [84].

Compounds 1 to 204 were prepared according to the methods of Reaction Examples 1, 2 and 3, and the results are shown below in the first group (group).

[First group (group)]

Comparative Example 1

(4,4 ', 4 &quot; -tris (N-naphthalen-2-yl) - &lt; / RTI &gt; N-phenylamino) -triphenylamine was used as a hole injection layer material and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) (30 nm) / a-NPD (30 nm) / compound a + compound b (30 nm) / Alq3 (30 nm)

/ LiF (0.5 nm) / Al (60 nm).

An anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning it in acetone, isopropyl alcohol and pure water for 15 minutes each, Ozone cleaning was used. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by the formula (a) and a compound represented by the formula (b) (8% doping) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in FIG. 1B. This is referred to as Comparative Sample 1.

Comparative Example 2

2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2-yl) -N-phenylamino) -triphenylamine was used as a hole injection layer material and? -NPD (naphthalene-1-yl) -N, N'-diphenylbenzidine was used as a hole transport layer material, (30 nm) / a-NPD (30 nm) / compound a + compound c (30 nm) / Alq3 (30 nm)

/ LiF (0.5 nm) / Al (60 nm).

An anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning it in acetone, isopropyl alcohol and pure water for 15 minutes each, Ozone cleaning was used. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound (a) represented by formula (a) and compound c (10% doped) represented by formula (c) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in FIG. 1B. This is referred to as Comparative Sample 2.

Comparative Example 3

2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2-yl) thiophene) is used as a host by using a compound represented by the formula -N-phenylamino) -triphenylamine was used as a hole injection layer material and? -NPD (naphthalene-1-yl) -N, N'-diphenylbenzidine was used as a hole transport layer material, (30 nm) / a-NPD (30 nm) / compound a + compound d (30 nm) / Alq3 (30 nm)

/ LiF (0.5 nm) / Al (60 nm).

An anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning it in acetone, isopropyl alcohol and pure water for 15 minutes each, Ozone cleaning was used. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound (a) represented by Formula (a) and compound d (8% doped) represented by Formula (d) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in FIG. 1B. This is referred to as Comparative Sample 3.

In this comparative example and the following comparative examples and embodiments, devices were fabricated by using an EL evaporator manufactured by DeVoiste.

(Formula a) < Formula b >

<Formula c> <Formula d>

Examples 1 to 145

Except that one of the compounds 1 to 204 represented by the general formulas (1) to (204) shown in the above Synthesis Example was used as the light-emitting layer host compound in place of the compound (a) as the light emitting layer host compound in the above Comparative Example 1 The structure of ITO / 2-TNATA (80 nm) /? -NPD (30 nm) / [one of host compounds 1 to 204 + compound b] (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / Al Was prepared. These are referred to as Samples 1 to 145, respectively.

Evaluation Example 1: Evaluation of luminescence characteristics of Comparative Sample 1 and Samples 1 to 145

Comparative Example 1 and Sample 1 to 145 were evaluated for light emission luminance, luminous efficiency and emission peak using Keithley SMU 235 and PR650, respectively, and the results are shown in the following [second group (group)]. The samples showed green emission peak values in the range of 516 to 525 nm.

[Second group (group)]

Samples 1 to 145 exhibited improved luminescence characteristics as compared to Comparative Sample 1, as shown in the above [second group (s)].

Examples 146 to 165

In the same manner as in Comparative Example 2, except that the compound (a) as the phosphorescent host compound of the above-mentioned Comparative Example 2 was used instead of the compound (a) Organic luminescence having a structure of 2-TNATA (80 nm) /? -NPD (30 nm) / [one of host compound 10 + compound c] (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / Al Device. These are referred to as Samples 146 to 165, respectively.

Evaluation Example 2: Evaluation of luminescence characteristics of Comparative Sample 2 and Samples 146 to 165

Comparative Example 2 and Samples 146 to 165 were evaluated for light emission luminance, light emission efficiency, and light emission peak using Keithley SMU 235 and PR650, respectively, and the results are shown in the following [Table 3]. The samples showed a red emission peak value in the range of 610 to 616 nm.

[Table 3]

As shown in [Table 3] above, Samples 146 to 165 exhibited improved luminescence characteristics compared to Comparative Sample 2.

Evaluation Example 4: Evaluation of life characteristics of Comparative Sample 1 and Samples 9, 21, 48, 60, 63, and 85

For the comparative sample 1 and the samples 9, 21, 48, 60, 63, and 85 , the intensity of light emission was reduced to 70% of the initial value based on the luminance 5000nit in the DC mode using the life evaluation equipment (LTS-1004C) The lifetime was evaluated by the time, and the results are shown in the following [Table 4].

Samples 9, 21, 48, 60, 63, and 85 showed improved lifespan characteristics as compared to Comparative Sample 1, as shown in Table 4 above.

In the above description, the conventional well-known technique is omitted, but a person skilled in the art can easily guess, deduce and reproduce it.

Claims (8)

A first electrode; A second electrode; And at least one organic layer between the first electrode and the second electrode, wherein the organic layer comprises an organic light-emitting compound represented by the following Formula F:
<Formula F>

{Formula F
X is N, S, Si or Se,
a1 and a2 are dependent on X,
Independently, 0 (zero) (when X is S or Se, a1 and a2 are all 0) (when X is N, a1 is 0)
A2 when X is N or a1 and a2 when X is Si are each a C1-C50 alkyl group; C6-C50 aryl group, or a C2-C50 heteroaryl group,


A is H, D, F, a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, a silyl group, a C 6 -C 50 aryl group, a C 2 -C 50 heteroaryl group, a C 2 -C 50 cycloalkyl group or a C 2 -C 50 heterocycloalkyl group,


R is an aromatic ring or an aliphatic ring,
Wherein each of B1 and B2 is independently selected from the group consisting of H, D, F, a C1-C50 alkyl group, a C1-C50 alkoxy group, a silyl group, a C6-C50 aryl group, a C2-C50 heteroaryl group, A heterocycloalkyl group,
b1 and b2 are zero when R is an aromatic ring, C1-C50 alkyl group when R is an aliphatic ring,


R1 and R2 are each independently
Wherein R 1 and R 2 together form a fused aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring together with the adjacent ring,


Wherein the formula (F) is any one of organic luminescent compounds represented by the following formulas (F1) to (F6) and (F11):
<Formula F1>

<Formula F2>

<Formula F3>

<Formula F4>

<Formula F5>

<Formula F6>

<Formula F11>

{In each of formulas F1 to F6 and F11,
A is H, D, F, a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, a silyl group, a C 6 -C 50 aryl group, a C 2 -C 50 heteroaryl group, a C 2 -C 50 cycloalkyl group or a C 2 -C 50 heterocycloalkyl group,


Wherein each of B1 and B2 is independently selected from the group consisting of H, D, F, a C1-C50 alkyl group, a C1-C50 alkoxy group, a silyl group, a C6-C50 aryl group, a C2-C50 heteroaryl group, A heterocycloalkyl group,


In Formula F1,
X1 and X2 are N,
D1 and D2 are any one of H, D and F,


In the above formula (F4)
D is a fused aromatic ring with adjacent rings, a group which forms a fused heteroaromatic ring}. delete The method of claim 1, wherein
The aryl group, heteroaryl group, cycloalkyl group and heterocycloalkyl group each have a substituent, and the substituent
A C1-C50 alkyl group; A C1-C50 alkoxy group; A C6-C50 aryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; A C2-C50 heteroaryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; A C5-C50 cycloalkyl group unsubstituted or substituted by a C1-C50 alkyl group or a C1-C50 alkoxy group; A C5-C50 heterocycloalkyl group unsubstituted or substituted with a C1-C20 alkyl group or a C1-C20 alkoxy group; Or a silyl group. &Lt; RTI ID = 0.0 &gt; 11. &lt; / RTI &gt; The method according to claim 1,
The aryl group, heteroaryl group, cycloalkyl group and heterocycloalkyl group
A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, A phenanthryl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group A heptadecenyl group, a fluorenyl group, a pyranthrenyl group, an obenyl group, a carbazolyl group, a dibenzofuranyl group, A thiophenyl group, a dibenzothiophenyl group, a thiophenyl group, an indolyl group, a purinyl group, a benzimidazolyl group, a quinolizinyl group, a benzothiophenyl group, a parathiazinyl group, a pyrrolyl group, a pyrazolyl group, an imidazolyl group, A thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, , Pyridinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thianthrenyl group, cyclopentyl group, cyclohexyl group, oxiranyl group, pyrrolidinyl group, pyrazolidinyl group, imidazoli (C6-C50 aryl) amino group, silyl group, and derivatives thereof, wherein the substituent group has at least one substituent selected from the group consisting of a halogen atom, a cyano group, a cyano group, a cyano group, a diethyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, The method according to claim 1,
Wherein the organic light emitting compound is represented by the following Chemical Formulas 64 to 163, 196, 197, and 204:

An organic light-emitting compound represented by the following formula (F):
<Formula F>

{Formula F
X is N, S, Si or Se,
a1 and a2 are dependent on X,
Independently, 0 (zero) (when X is S or Se, a1 and a2 are all 0) (when X is N, a1 is 0)
A2 when X is N or a1 and a2 when X is Si are each a C1-C50 alkyl group; C6-C50 aryl group, or a C2-C50 heteroaryl group,


A is H, D, F, a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, a silyl group, a C 6 -C 50 aryl group, a C 2 -C 50 heteroaryl group, a C 2 -C 50 cycloalkyl group or a C 2 -C 50 heterocycloalkyl group,


R is an aromatic ring or an aliphatic ring,
Wherein each of B1 and B2 is independently selected from the group consisting of H, D, F, a C1-C50 alkyl group, a C1-C50 alkoxy group, a silyl group, a C6-C50 aryl group, a C2-C50 heteroaryl group, A heterocycloalkyl group,
b1 and b2 are zero when R is an aromatic ring, C1-C50 alkyl group when R is an aliphatic ring,


R1 and R2 are each independently
Wherein R 1 and R 2 together form a fused aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring together with the adjacent ring,


Wherein the formula (F) is any one of organic luminescent compounds represented by the following formulas (F1) to (F6) and (F11)
<Formula F1>

<Formula F2>

<Formula F3>

<Formula F4>

<Formula F5>

<Formula F6>

<Formula F11>

{In each of formulas F1 to F6 and F11,
A is H, D, F, a C 1 -C 50 alkyl group, a C 1 -C 50 alkoxy group, a silyl group, a C 6 -C 50 aryl group, a C 2 -C 50 heteroaryl group, a C 2 -C 50 cycloalkyl group or a C 2 -C 50 heterocycloalkyl group,


Wherein each of B1 and B2 is independently selected from the group consisting of H, D, F, a C1-C50 alkyl group, a C1-C50 alkoxy group, a silyl group, a C6-C50 aryl group, a C2-C50 heteroaryl group, A heterocycloalkyl group,


In Formula F1,
X1 and X2 are N,
D1 and D2 are any one of H, D and F,


In the above formula (F4)
D is a fused aromatic ring with adjacent rings, a group which forms a fused heteroaromatic ring}. delete The method according to claim 6,
Wherein the organic luminescent compound is represented by the following Chemical Formulas 64 to 163, 196, 197, 204: