KR20120081539A - Organic light compound and organic light device using the same - Google Patents

Abstract

PURPOSE: An organic electroluminescent device is provided to provide high luminance efficiency, high luminance, high color purity, and extremely improved life time. CONSTITUTION: An organic electroluminescent comprises a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. The organic layer comprises an organic luminescent compound in chemical formula F1a, F1b, or F2. In the chemical formulas, P1 and P2 is selected from a group consisting of a C5-40 aryl group, a C5-40 heteroaryl group, a C5-40 aryloxy group, a C5-40 arylamino group, C5-40 diarylamino group, C6-40 arylalkyl group, or a group forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring together with a neighboring group.

Description

Organic light emitting compound and organic optical device using the same {ORGANIC LIGHT COMPOUND AND ORGANIC LIGHT DEVICE USING THE SAME}

The present invention relates to an organic light emitting compound, in particular a carbazole-based derivative and an organic optical device using the same, and more particularly, to an organic light emitting device capable of realizing excellent luminous efficiency, luminous brightness, color purity and luminous lifetime and its use The present invention relates to an organic light emitting compound or a photovoltaic device for photovoltaic power generation and an optical compound used therefor.

In general, organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material. That is, when the organic material layer is positioned between the anode and the cathode, a voltage is applied between the two electrodes, and holes are injected into the organic material and electrons are injected into the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground, they shine.

In the 1950s, Bernanose applied high alternating voltage to the polymer thin film containing organic pigments and observed luminescence from the organic thin film.In 1965, singlet excitons were generated by applying a current to anthracene single crystal to generate blue Fluorescence was obtained.

As one method for making an organic electroluminescent device efficiently, research has been conducted to manufacture an organic material layer in a multi-layer structure instead of a single layer. In 1987, Tang presented an organic electroluminescent device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer, and most organic electroluminescent devices currently used are hole injection that accepts holes as a substrate, an anode, and an anode. Layer, a hole transporting layer that transfers holes, a light emitting layer that emits light by recombining holes and electrons,

It consists of an electron carrying layer which transmits, an electron injection layer which receives an electron from a cathode, and a cathode. The reason why the organic EL device is manufactured in a multi-layer is that the movement speeds of the holes and the electrons are different. This is because light emission efficiency can be improved by balancing holes and electrons in the device.

The earliest reports on the material of electron transport include oxadiazole derivatives (PBDs). It has since been reported that triazole derivatives (TAZ) and phenanthroline derivatives (BCP) exhibit electron transport properties. The electron transport layer is a good candidate for the organic monomolecular materials such as organometallic complexes having excellent electron stability and electron transfer speed, and Alq3 having high stability and electron affinity is the best candidate. Is being used. Also, species

Known electron transporting materials are known as flavon derivatives published by Sanyo, germanium and silicon cyclopentadiene derivatives from Chiso. (Japanese Laid-Open Patent Publication No. 1998-017860, Japanese Laid-Open Patent Publication No. 1999-087067).

In addition, a number of organic monomolecular materials having imidazole group, oxazole group, and thiazole group have been reported as materials for conventional electron injection and transport layers. However, before these materials were reported as electron transport materials, Motorola's EU0700917 A2 has already reported application of metal complex compounds of these materials to the blue light emitting layer or the cyan light emitting layer of an organic light emitting device.

TPBI, published by Kodak in 1996 and described in US Pat. No. 5,645,948, is known as a representative electron transport layer material having an imidazole group, and its structure has three N-phenyl benzs at 1,3,5 substitution positions of benzene. It contains an imidazole group and functionally blocks electrons from the light emitting layer as well as the ability to transfer electrons, but has a problem of low thermal stability for practical application.

In addition, the electron transporting materials disclosed in Japanese Patent Application Laid-Open No. 11-345686 report that they contain oxazole group and thiazole group and can be applied to the light emitting layer, but have reached practical use in terms of driving voltage, luminance and lifetime of the device. I can't.

Therefore, in order to overcome the problems of the prior art as described above and to further improve the characteristics of the organic EL device, development of a more stable and efficient material that can be used as an electron transporting material in the organic EL device is still required.

The first technical problem to be achieved by the present invention is to provide a new organic light emitting compound that can be applied to organic optical devices, in particular organic electroluminescent devices.

The second technical problem to be achieved by the present invention is to provide an organic electroluminescent device and a photovoltaic device for photovoltaic power generation, including the novel compound, low driving voltage, improved luminous efficiency, brightness, color purity, thermal stability and lifetime. .

The organic light emitting compound and the organic optical device using the same according to the present invention is based on an organic light emitting compound represented by the following formula F1a, F2, F3, F4a or F4b:

<Formula F1a>

<Formula F2>

<Formula F3>

<Formula F4a>

<Formula F4b>

In the above formula

P1, P2 and P3 are each independently

C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group or Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group,

A1 and A2 are each independently

H, D, F, C1-C40 alkyl group, C5-C40 aryl group, C5-C40 heteroaryl group, C5-C40 aryloxy group, C1-C40 alkyloxy group, C5-C40 arylamino group, An aliphatic ring, a fused aromatic ring selected from the group consisting of C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group, C3 ~ C40 cycloalkyl group, and C3 ~ C40 heterocycloalkyl group or fused with an adjacent group; Groups forming a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

In addition, the organic light emitting compound and the organic optical device using the same according to the present invention is based on the organic light emitting compound of the formula 1 to 200:

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 an organic light emitting device and an organic light emitting compound, or an organic optical device and a photo compound for solar power generation

Hereinafter, the present invention will be described in detail.

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

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. In this application, the terms “comprises” or “consists” are intended to indicate that there is a feature, number, step, action, component, part, or combination thereof described on the specification, but one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, parts, or combinations thereof.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by one of ordinary skill in the art 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 can be used in various ways such as various organic membranes between the first electrode and the second electrode by developing a carbazole derivative, such as an electron transport layer (ETM), a light emitting layer (EML), a hole transport layer (HTM) The present invention aims to develop materials that maximize performance as OLED materials and improve performance such as increasing efficiency and decreasing driving voltage.

In the present specification, the organic light emitting compound is a compound used for an organic optical device, and is not necessarily limited to a compound capable of emitting light. It can be used in any layer that constitutes the ruler.

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 optical device according to the first aspect of the present invention, the first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode, wherein the organic film comprises an organic light emitting compound of formula F1a, F2, F3, F4a or F4b:

<Formula F1a>

<Formula F2>

<Formula F3>

<Formula F4a>

<Formula F4b>

In the above formula

P1, P2 and P3 are each independently

C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group or Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group,

A1 and A2 are each independently

H, D, F, C1-C40 alkyl group, C5-C40 aryl group, C5-C40 heteroaryl group, C5-C40 aryloxy group, C1-C40 alkyloxy group, C5-C40 arylamino group, An aliphatic ring, a fused aromatic ring selected from the group consisting of C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group, C3 ~ C40 cycloalkyl group, and C3 ~ C40 heterocycloalkyl group or fused with an adjacent group; Groups forming a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

In addition, the organic optical device according to the first aspect of the present invention, the first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode, the organic film comprising an organic light emitting compound of formula F1b:

<Formula F1b>

The inventor of the present invention selects P1, P2, P3 and A1, A2 from the substituent of the organic light emitting compound of Formula F1a, F2, F3, F4a or F4b,

Organic derivatives that can be used as various organic films between the first electrode and the second electrode such as electron transport layer (ETM), light emitting layer (EML), hole transport layer (HTM), etc.

Develop an organic optical device using the same,

When used as an organic light emitting device, it has been found that performance improvement such as increased efficiency and driving voltage can be improved, and the ability as an OLED material can be maximized, and in particular, the light emission life is significantly improved.

If this is applied to photovoltaic devices and photochemical fields for photovoltaic power generation, it is expected to obtain excellent power generation efficiency.

Hereinafter, an organic light emitting compound of Formula F1a, F1b, F2, F3, F4a, or F4b or an organic light emitting compound of Formulas 1 to 200 will be described with reference to an organic light emitting device, but the present invention should not be construed as limiting thereto. .

The organic light emitting compound of Formula F1a, F1b, F2, F3, F4a or F4b or the organic light emitting compound of Formulas 1 to 200 is suitable as a material forming an organic film interposed between the first electrode and the second electrode of the organic optical device. The organic light emitting compound of Formula F1a, F1b, F2, F3, F4a or F4b or the organic light emitting compound of Formulas 1 to 200 is suitable for use in organic films of organic light emitting devices, in particular, hole transport layers, hole injection layers or light emitting layers, and a host material It is also used as a dopant material. The organic light emitting compound of Formula F1a, F2, F3, F4a or F4b provides a color of blue to green and is suitable for use in a white light emitting device.

More specifically, in Formula F1a (compounds 1 to 200 correspond to 1 to 47, Formula F1b corresponds to compound 48) or F2 (compounds 50 to 53 and 56 in compounds 1 to 200 correspond to)

P1 and P2 are each independently

C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group or Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group.

In Formula F3 (corresponding to 54, 55 and 57 to 60 in the following Compounds 1 to 200)

P1 and P2 are each independently

H, D, F, C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group A group selected from the group consisting of or adjacent groups to form a fused aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

In Formulas F4a (corresponding to 84 to 88 and 92 and 96 in the following Compounds 1 to 200) and F4b (corresponding to 89 to 91 and 93, 94 and 95 in the following Compounds 1 to 200)

P1, P2 and P3 are each independently

C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group or Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group,

A1 and A2 are each independently

H, D, F, C1-C40 alkyl group, C5-C40 aryl group, C5-C40 heteroaryl group, C5-C40 aryloxy group, C1-C40 alkyloxy group, C5-C40 arylamino group, An aliphatic ring, a fused aromatic ring selected from the group consisting of C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group, C3 ~ C40 cycloalkyl group, and C3 ~ C40 heterocycloalkyl group or fused with an adjacent group; Groups forming a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

In the above formulas F1a, F2, F3, F4a or F4b, each formula is commonly represented by P1, P2, P3, A1, A2, but in each formula they are irrelevant.

Meanwhile, the C1 to C40 alkyl group, the C2 to C40 alkenyl group, the C2 to C40 alkynyl group, the C5 to C40 aryl group, the C5 to C40 heteroaryl group, C5 C40-C40 aryloxy group, C1-C40 alkyloxy group, C5-C40 arylamino group, C5-C40 diarylamino group, C6-C40 arylalkyl group, C3-C40 cycloalkyl group, and C3-C40 heterocyclo Alkyl groups

Each independently D, F, halogen, nitrile group, nitro group, C1 ~ C40 alkyl group, C2 ~ C40 alkenyl group, C1 ~ C40 alkoxy group, C1 ~ C40 amino group, C3 ~ C40 cycloalkyl group, C3 ~ It is preferably substituted or unsubstituted with one or more selected from the group consisting of C40 heterocycloalkyl group, C5 ~ C40 aryl group and C5 ~ C40 heteroaryl group.

Moreover, said C1-C40 alkyl group of said P1, P2, P3, A1, A2, C2-C40 alkenyl group, C2-C40 alkynyl group, C5-C40 aryl group, C5-C40 heteroaryl group, C5- ~ C40 aryloxy group, C1-C40 alkyloxy group, C5-C40 arylamino group, C5-C40 diarylamino group, C6-C40 arylalkyl group, C3-C40 cycloalkyl group, and C3-C40 heterocycloalkyl group Of the substituents introduced in

C1 ~ C40 alkyl group, C2 ~ C40 alkenyl group, C1 ~ C40 alkoxy group, C1 ~ C40 amino group, C3 ~ C40 cycloalkyl group, C3 ~ C40 heterocycloalkyl group, C5 ~ C40 aryl group and C5 ~~ C40 heteroaryl group

Each independently D, F, halogen, nitrile group, nitro group, C1 ~ C40 alkyl group, C2 ~ C40 alkenyl group, C1 ~ C40 alkoxy group, C1 ~ C40 amino group, C3 ~ C40 cycloalkyl group, C3 ~ Further substituted with at least one second substituent selected from the group consisting of C40 heterocycloalkyl group, C5 ~ C40 aryl group and C5 ~ C40 heteroaryl group; Or it is preferable to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with an adjacent group or to form a spiro bond.

Furthermore, said C1-C40 alkyl group, C2-C40 alkenyl group, C2-C40 alkynyl group, C5-C40 aryl group, C5-C40 heteroaryl group, C5 of said P1, P2, P3, A1, A2 C40-C40 aryloxy group, C1-C40 alkyloxy group, C5-C40 arylamino group, C5-C40 diarylamino group, C6-C40 arylalkyl group, C3-C40 cycloalkyl group, and C3-C40 heterocyclo Substituents introduced into the alkyl group

D, F, phenyl group, tolyl group, biphenyl group, pentalenyl group, indenyl group, naphthyl group, biphenylenyl group, anthracenyl group, benzoanthracenyl group, azurenyl group, heptarenyl group, acenaphthylyl group, phenna Renyl group, methyl anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pisenyl group, perrylenyl group, chloroperylenyl group, pentaphenyl group, pentaxenyl group, tetraphenylenyl group, hexa Phenyl group, hexasenyl group, rubisenyl group, coronyl group, trinaphthylenyl group, heptaphenyl group, heptasenyl group, fluorenyl group, pyrantrenyl group, obarenyl group, carbazolyl group, dibenzofuranyl group, dibenzo Thiophenyl 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, pyridazinyl, pyrimidinyl, pyrazinyl, thianthrenyl, cyclopentyl, cyclohexyl, oxiranyl, pyrrolidinyl, pyrazolidinyl, imidazolidi It is preferable to select from the group consisting of a silyl group, a piperidinyl group, a piperazinyl group, a morpholinyl group, a di (C6-C50 aryl) amino group, a silane group and derivatives thereof.

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 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, P, Si, and Se.

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, P, Si, and Se. .

When one or more hydrogen of the aryl group and heteroaryl group is substituted, their substituents are C1-C50 alkyl group; C1-C50 alkoxy group; A C6-C50 aryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; 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 optical device according to the first aspect of the present invention, the first electrode; A second electrode; And at least one organic film between the first electrode and the second electrode.

The organic light emitting compound used in the organic optical device of the present invention may have a structure of Chemical Formulas 1 to 200 (hereinafter, the chemical formulas are omitted, and only the numbers are described), but are not limited thereto.

One

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The organic light emitting compound according to the present invention represented by the compound of Formula F1a, F2, F3, F4a or F4b or the organic light emitting compound of Formula 1 to 200 can be synthesized using a conventional synthesis method, The detailed synthetic route refers to the schemes of the following synthesis examples. The organic light emitting compound of Formula F1a, F1b, F2, F3, F4a or F4b or the organic light emitting compound of Formulas 1 to 200 is suitable for use in an organic film, particularly a hole transport layer, a hole injection layer or a light emitting layer of an organic optical device. 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.

In this case, at least one of the hole transport layer, the hole injection 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. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm. In addition, the compound 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 on the substrate is formed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Herein, a substrate used in a conventional organic optical 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. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, are used as the material for the first electrode.

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

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 Formula a as described above.

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

(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. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.

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

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

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

The luminescent layer may comprise a compound of formula (a) according to the invention as described above. At this time, the compound of formula a may be used with a suitable known host material or may be used with a known dopant material.

It is also possible to use the compound of formula (A) 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 generally 0.01 to 15 parts by weight based on 100 parts by weight of the host. The thickness of the light emitting layer may be about 100 kPa to 1000 kPa, preferably 200 kPa to 600 kPa.

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 that can be used include, for example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and BCP.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. 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.

When the electron transport layer is formed by the vacuum deposition method or the spin coating method, the conditions vary depending on the compound used, but are generally selected from the ranges of conditions almost the same as that of the formation of the hole injection layer. The electron transport layer material 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 electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. 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, Li 2 O, BaO or the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

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

Finally, the second electrode 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, and 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 Chemical Formula a, and more specifically, may be represented by Chemical Formulas 1 to 200. Details of the compounds are the same as those described for the above-mentioned organic feet and devices.

Hereinafter, the reaction examples and comparative examples of the present invention will be specifically illustrated, but the present invention is not limited to the following synthesis examples and examples. In the following 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 the formula (1) is represented by compound 1.

[Reaction Example 1] Synthesis of Compound [1]

Preparation of Intermediate Compound [1-1]

50g (247.5mmol) of 1-bromo-2-nitrobenzene, 51g (297.0mmol) of naphthalene-2-boronic acid, 5.72g (4.95mmol) of tetrakis (triphenylphosphine) palladium and 51.3g of sodium carbonate (371.27 mmol) was added and 1.2 L of 1,4-dioxane and 200 ml of distilled water were stirred under reflux for 24 hours in a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and purified by silica gel chromatography to obtain 45.6 g (74%) of an intermediate compound [1-1] as an off-white solid.

Preparation of Intermediate Compounds [1-2] and [1-3]

47.6 g (182.9 mmol) of the intermediate compound [1-1] and 152.0 ml (914.7 mmol) of triethyl phosphite were added to a 2 L reaction flask, and 900 ml of cumene was added and stirred under reflux for 24 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was concentrated under reduced pressure using high vacuum, and purified by silica gel chromatography to obtain 19g (46%) of the intermediate compound [1-2] and 17.4 (42%) of the white solid.

Preparation of Compound [1]

Intermediate Compound [1-2] 10 g (46.0 mmol), bromobenzene 8.7 ml (55.2 mmol), palladium (II) acetate 0.21 g (0.92 mmol), potassium t-butoxide 6.6 g (69.0 mmol), tri-t -1.1 ml (4.6 mmol) of butylphosphine was added and 250 ml of xylene was added and stirred under reflux for 24 hours while flowing nitrogen. After completion of the reaction, 200 ml of methanol was added to crystallize, and the resultant was filtered and purified under reduced pressure with silica gel chromatography to obtain 9.8 g (73%) of the target compound [1] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.55 to 8.51 (m, 2H), 8.16 to 8.12 (m, 2H), 7.94 (d, 1H), 7.67 to 7.45 (m, 8H), 7.33 to 7.25 ( m, 2H)

MS / FAB: 293 (M ⁺ )

1 to 46, 48 to 52, 54 to 58, 60, 61, 63, 65 to 88, 92, 97 to 99, 104, 105, 107 to 155, 157 to 167, 170, 172, the compounds of 198 to 200 were prepared, and the results are shown in the following [Table 1].

[First vote group]

[Reaction Example 2] Synthesis of Compound [47]

Preparation of Intermediate Compound [47-1]

Dissolve 10 g (34.1 mmol) of compound [1] with dichloromethane. 6.7 g (37.5 mmol) of enbromosuccinimide was slowly added dropwise to the reaction solution at 0 ° C. After stirring for 12 hours at room temperature, dichloromethane is further extracted, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography to obtain 10.4 g (82%) of an intermediate compound [47-1] as an off-white solid.

Preparation of Compound [47]

Synthesis of Intermediate Compound [47-1], diphenylamine, palladium (II) acetate, potassium t-butoxide and tri-t-butylphosphine in the same manner as in Synthesis Example 1 11.3 g (88%) of the title compound [47] was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.41 (d, 1H), 8.08 ~ 8.02 (m, 3H), 7.57 ~ 7.35 (m, 8H), 7.10 (t, 4H), 6.71 (t, 2H) , 6.53 to 6.50 (m, 5H), 5.75 (d, 1H)

MS / FAB: 460 (M ⁺ )

Compounds of 47, 53, 59, 62, 64, 89-91, 93-96, 100-103, 106, 156, 168, 169, 171, and 173 were prepared according to the method of Reaction Example 2 below. 2 votes group] shows the result.

[2nd vote group]

[Reaction Example 3] Synthesis of Compound [174]

Preparation of Intermediate Compound [174-1]

10 g (27.9 mmol) of the intermediate compound [47-1] were dissolved in 150 mL of tetrahydrofuran under a nitrogen stream in a 1 L reaction flask, and 13.4 mL (33.5 mmol) of 2.5M butyllithium was added dropwise at -78 ° C. After stirring for 30 minutes at the same temperature, 3.7 mL (33.5 mmol) of trimethylborate was added. After completion of the reaction, the reaction mixture was poured into 1N aqueous hydrochloric acid solution and extracted with ethyl acetate. Recrystallization with dichloromethane and normal hexane after separation of the organic layer gave 5.8 g (62%) of an intermediate compound [174-1] as a white solid.

Preparation of Intermediate Compound [174-2]

Synthesis of Yellow solid using intermediate compound [174-1], intermediate compound [47-1], tetrakis (triphenylphosphine) palladium, potassium carbonate, 1,4-dioxane, in the same manner as in Synthesis Example 1. 5.6 g (71%) of compound [174-2] was obtained.

Preparation of Compound [174-3]

In the same manner as in Synthesis Example 2, 6.2 g (87%) of the target compound [174-3] was obtained using the intermediate compound [174-2], enbromosuccinimide, and dichloromethane.

Preparation of Compound [174]

In the same manner as in Synthesis Example 1, an intermediate compound [174-3], diphenylamine, palladium (II) acetate, potassium t-butoxide, tri-t-butylphosphine, and light yellow solid were obtained using xylene. the target compound [174] 5.1g (67%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.19-8.02 (m, 8H), 7.77 (s, 2H), 7.59-7.72 (m, 22H), 6.83-6.65 (m, 14H)

MS / FAB: 919 (M ⁺ )

174 to 177 compounds were prepared according to the method of Reaction Example 3, and the results are shown in the following [Table 3].

[Table 3]

Reaction Example 4 Synthesis of Compound

Preparation of Intermediate Compound [178-1]

30 g (184.0 mmol) of 2-bromothiophene was dissolved in 1 L of tetrahydrofuran under a stream of nitrogen in a 2 L reaction flask, and 88.3 mL (220.8 mmol) of 2.5M butyllithium was added dropwise at -78 ° C. After stirring for 10 minutes at the same temperature, 59.9 mL (220.8 mmol) of tributyltin chloride was added. After completion of the reaction, the organic layer obtained by layer separation with ethyl acetate / distilled water is removed with anhydrous magnesium sulfate and distilled under reduced pressure. The concentrate was separated and purified through column chromatography to obtain 35.7 g (52%) of an intermediate compound [178-1] as a pale yellow oil.

Preparation of Intermediate Compound [178-2]

Synthesis method as in Synthesis Example 1, a yellow solid using an intermediate compound [178-1], 1-bromo-2-nitrobenzene, tetrakis (triphenylphosphine) palladium, potassium carbonate, and 1,4-dioxane 11.0 g (72%) of the title compound [178-2] was obtained.

Preparation of Intermediate Compound [178-3]

In the same manner as in Synthesis Example 1, 8.1 g (87%) of an intermediate compound [178-3] was obtained using an intermediate compound [178-3], triethyl phosphite, and cumene.

Preparation of Compound [178]

In the same manner as in Synthesis Example 1, an intermediate compound [178-3], bromobenzene, palladium (II) acetate, potassium t-butoxide, tri-t-butylphosphine were added, and xylene was used to form a light yellow solid. the target compound [178] 8.7g (75%) of the title compound.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.43 (d, 1H), 7.95 (d, 1H), 7.51 ~ 7.22 (m, 8H), 6.97 (d, 1H)

MS / FAB: 249 (M ⁺ )

Compounds 178 to 197 were prepared according to the method of Reaction Example 4, and the results are shown in the following [Table 4].

[Table 4]

Comparative Example 1

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

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On 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 b represented by Formula b (3% doping) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum deposited on the electron transport layer to prepare an organic light emitting device as shown in Table 6. This is referred to as Comparative Sample 1.

<Formula a> <Formula b>

                <Formula c>

Examples 62, 64, 87, 92, 96, 99, 105, 106, 156, 163-165, 168, 169, 171-177

In Comparative Example 1, instead of compound C (2-TNATA) as the hole transport layer compound, Chemical Formulas 62, 64, 87, 92, 96, 99, 105, 106, 156, 163 to 165, 168, 169, Comparative Examples except that compounds 62, 64, 87, 92, 96, 99, 105, 106, 156, 163-165, 168, 169, and 171-177 represented by 171 to 177 were used as the hole transport layer compounds, respectively. ITO / Compound 62, 64, 87, 92, 96, 99, 105, 106, 156, 163-165, 168, 169, 171-177 (80nm) / α-NPD (30nm) / Compound a + An organic light emitting diode having a structure of Compound b (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm) was prepared. These are called samples 62, 64, 87, 92, 96, 99, 105, 106, 156, 163-165, 168, 169, 171-177, respectively.

Evaluation Example 1: Evaluation of emission characteristics of Comparative Sample 1 and Samples 62, 64, 87, 92, 96, 99, 105, 106, 156, 163-165, 168, 169, 171-177

For Comparative Sample 1 and Samples 62, 64, 87, 92, 96, 99, 105, 106, 156, 163 ~ 165, 168, 169, 171 ~ 177, Luminous Intensity, Luminous Efficiency using Keithley SMU 235, PR650 , The emission peaks were respectively evaluated, and the results are shown in the following [Table 5]. The samples showed green emission peaks in the range of 512-526 nm.

[Table 5]

As shown in [Table 5], the samples 62, 64, 87, 92, 96, 99, 105, 106, 156, 163-165, 168, 169, 171-177 have improved light emission characteristics compared to Comparative Sample 1. Indicated.

Examples 1 to 142

In Comparative Example 1, as the light emitting layer fluorescent dopant compound, Chemical Formulas 1 to 61, 63, 66 to 86, 88 to 91, 93, 94, 95, 97, 98, 100 to 104, 107 disclosed in Synthesis Example instead of compound b were used. Compounds 1-61, 63, 66-86, 88-91, 93, 94, 95, 97, 98, 100-104, 107- represented by 155, 157-162, 166, 167, 170, 178-201 155, 157-162, 166, 167, 170, 178-201 were used as ITO / 2-TNATA (80 nm) / α-NPD ( 30 nm) / (Compound A + fluorescent green host compound 1-61, 63, 66-86, 88-91, 93, 94, 95, 97, 98, 100-104, 107-155, 157-162, 166, 167 (3%)] (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm) of 170, 178 to 201 were manufactured. These are called samples 1-61, 63, 66-86, 88-91, 93, 94, 95, 97, 98, 100-104, 107-155, 157-162, 166, 167, 170, 178-201, respectively. .

Evaluation Example 2: Comparative Sample 1 and Samples 1 to 61, 63, 66 to 86, 88 to 91, 93, 94, 95, 97, 98, 100 to 104, 107 to 155, 157 to 162, 166, 167 and 170 Evaluation of Luminescence Characteristics of 178 ~ 201

Comparative Sample 1 and Sample 1 ~ 61, 63, 66 ~ 86, 88 ~ 91, 93, 94, 95, 97, 98, 100 ~ 104, 107 ~ 155, 157 ~ 162, 166, 167, 170, 178 ~ 201 The light emission luminance, the light emission efficiency, and the light emission peak were evaluated using Keithley SMU 235 and PR650, respectively, and the results are shown in the following [Table 6]. The samples showed green emission peaks in the range of 512-526 nm.

[Table 6]

Samples 1-61, 63, 66-86, 88-91, 93, 94, 95, 97, 98, 100-104, 107-155, 157-162, as shown in the above [Table 6] , 166, 167, 170, and 178 to 201 showed improved luminescence properties compared to Comparative Sample 1.

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

Claims (10)

A first electrode; A second electrode; And an organic optical device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film comprises an organic light emitting compound represented by Formula F1a, F1b, or F2:
<Formula F1a>

<Formula F1b>

<Formula F2>

In Formula F1a or F2
P1 and P2 are each independently
C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group or ; Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group. A first electrode; A second electrode; And an organic optical device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film comprises an organic light emitting compound represented by Formula F3:
<Formula F3>

In Formula F3
P1 and P2 are each independently
H, D, F, C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group Selected from the group consisting of; Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group. 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 of Formula F4a or F4b:
<Formula F4a>

<Formula F4b>

In Formula F4a or F4b
P1, P2 and P3 are each independently
C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group or ; Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group,


In Formula F4a
A1 and A2 are each independently
H, D,
C1-C40 alkyl group, C5-C40 aryl group, C5-C40 heteroaryl group, C5-C40 aryloxy group, C1-C40 alkyloxy group, C5-C40 arylamino group, C5-C40 diaryl Amino group, C6 ~ C40 arylalkyl group, C3 ~ C40 cycloalkyl group and C3 ~ C40 heterocycloalkyl group; Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group. The method according to any one of claims 1 to 3,
An organic optical device characterized in that the organic light emitting compound is represented by the formula 1 to 60 or 84 to 96:

A first electrode; A second electrode; And an organic optical 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 represented by Chemical Formula 61 to 83 or 97 to 200. device:

The method according to any one of claims 1 to 3,
C1 ~ C40 alkyl group, C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C1 ~ C40 alkyloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group, C3 ~ C40 cycloalkyl group and C3 ~ C40 heterocycloalkyl group
Each independently D, F, halogen, nitrile group, nitro group, C1 ~ C40 alkyl group, C2 ~ C40 alkenyl group, C1 ~ C40 alkoxy group, C1 ~ C40 amino group, C3 ~ C40 cycloalkyl group, C3 ~ An organic photo device, which is unsubstituted or substituted with one or more selected from the group consisting of a C40 heterocycloalkyl group, a C5 to C40 aryl group, and a C5 to C40 heteroaryl group. The method according to any one of claims 1 to 3,
Substituents of the aryl group, heteroaryl group, cycloalkyl group and heterocycloalkyl group,
A C1-C50 alkyl group; C1-C50 alkoxy group; A C6-C50 aryl group unsubstituted or substituted with a C1-C50 alkyl group or a C1-C50 alkoxy group; 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; C5-C50 heterocycloalkyl group which is unsubstituted or substituted with a C1-C20 alkyl group or a C1-C20 alkoxy group; Or one or more substituents selected from the group consisting of a silane group. The method according to any one of claims 1 to 3,
P1, P2 and P3 and A1 and A2 are each independently
Phenyl group, tolyl group, biphenyl group, pentarenyl group, indenyl group, naphthyl group, biphenylenyl group, anthracenyl group, benzoanthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group, methyl Anthryl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pisenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl 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, dibenzofuranyl group, dibenzothiophenyl group, thio Phenyl group, indolyl group, furinyl group, benzimidazolyl group, quinolinyl group, benzothiophenyl group, parathiazinyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, imidazolinyl group, oxazolyl group, thiazolyl group , Triazolyl group, tetrazolyl group, oxadiazolyl group, pyri Dinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, thianthrenyl group, thianthrenyl group, cyclopentyl group, cyclohexyl group, oxiranyl group, pyrrolidinyl group, pyrazolidinyl group, imidazolidinyl group An organic optical device selected from the group consisting of a piperidinyl group, a piperazinyl group, a morpholinyl group, a di (C6-C50 aryl) amino group and derivatives thereof. An organic light emitting compound represented by the following formula F1a, F2, F3, F4a or F4b:
<Formula F1a>

<Formula F2>

<Formula F3>

<Formula F4a>

<Formula F4b>

In the above formula
P1, P2 and P3 are each independently
C5 ~ C40 aryl group, C5 ~ C40 heteroaryl group, C5 ~ C40 aryloxy group, C5 ~ C40 arylamino group, C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group or Or a group which forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group,


A1 and A2 are each independently
H, D, F, C1-C40 alkyl group, C5-C40 aryl group, C5-C40 heteroaryl group, C5-C40 aryloxy group, C1-C40 alkyloxy group, C5-C40 arylamino group, An aliphatic ring, a fused aromatic ring selected from the group consisting of C5 ~ C40 diarylamino group, C6 ~ C40 arylalkyl group, C3 ~ C40 cycloalkyl group, and C3 ~ C40 heterocycloalkyl group or fused with an adjacent group; Groups forming a condensed heteroaliphatic ring or a condensed heteroaromatic ring. An organic light emitting compound represented by Formula 1 to 200: