KR101851703B1 - Novel compounds for organic light-emitting diode and organic light-emitting diode including the same - Google Patents

Abstract

상기 [화학식 B]에서 고리그룹 A1 내지 A3, 구조식 Q1 및 Q2, R1 및 R2, L1 내지 L4, Ar1 내지 Ar4, E 및 F는 발명의 상세한 설명에 기재된 바와 같다. The present invention relates to a compound represented by the following formula (B) and an organic light emitting device comprising the same.
[Chemical Formula B]

The ring groups A1 to A3, the structural formulas Q1 and Q2, R1 and R2, L1 to L4, Ar1 to Ar4, E and F in the above formula (B) are as described in the description of the invention.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel organic light-emitting compound and an organic light-

The present invention relates to a novel compound for an organic light emitting device and an organic light emitting device comprising the same, and more particularly to a compound for an organic light emitting device having excellent device characteristics such as low voltage driving and luminescence efficiency when used as a fluorescent host, And an organic light emitting device including the same.

The organic light emitting diode (OLED) is a display using a self-luminous phenomenon. The organic light emitting diode (OLED) has a wide viewing angle and is thinner and lighter than a liquid crystal display and has a fast response speed. ) Applications for display or illumination are expected.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism .

On the other hand, when only one material is used as the light emitting material, there arises a problem that the maximum light emitting wavelength shifts to a long wavelength due to intermolecular interaction, the color purity drops, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system can be used as a light emitting material to increase the efficiency of light emission through the transition.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

 As a prior art related to the host compound in such a light emitting layer, Japanese Patent Registration No. 10-1092006 (Dec. 12, 2011) discloses an organic light emitting device comprising an anthracene derivative in which a phenyl group having a substituent is bonded at both ends of an anthracene structure, And Patent Document 10-2006-0113954 (Nov. 3, 2006) discloses a technique relating to an organic light emitting device including an asymmetric anthracene derivative of a specific structure in a light emitting medium layer.

However, despite the fact that various kinds of compounds for use in the light emitting layer of the organic light emitting device including the above-described conventional techniques have been produced, there is a need to develop a light emitting layer material for an organic light emitting device capable of driving at low voltage, It is a constantly demanding situation.

Patent Registration No. 10-1092006 (December, 2011)

Patent Document 10-2006-0113954 (November 3, 2006)

Accordingly, the first technical object of the present invention is to provide a compound for an organic light emitting device which can be used for a light emitting layer of an organic light emitting device and which has excellent device characteristics such as low voltage driving and light emitting efficiency.

A second object of the present invention is to provide an organic light emitting device comprising the compound.

In order to achieve the first technical object, the present invention provides an organic luminescent compound represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

A1, A2, E and F are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring, An aromatic heterocycle having 2 to 40 carbon atoms;

Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a condensed ring by forming a 5-membered ring with carbon atoms connected to the substituents R1 and R2;

The linking groups L1 to L4 are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkinylene group having 2 to 60 carbon atoms, A substituted or unsubstituted alkylene group having 2 to 60 carbon atoms, an alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

M is any one selected from NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S, Se;

The substituents R ₁ to R ₉ and Ar ₁ to Ar 4 are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms , A substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 A substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms , A substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group,

The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be one of N, O, P, Si, S, Ge , Se, and Te;

Each of s1 to s4 is an integer of 1 to 3, and when each of them is 2 or more, each of the linking groups L1 to L4 is the same or different from each other,

X is an integer of 1 or 2, y and z are the same or different and independently of one another an integer of 0 to 3,

In the formula (A), two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) to form a condensed ring,

In the formula (B), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula (Q2) to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) ≪ / RTI >

The 'substituted' in the above 'substituted or unsubstituted' means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 1 to 24 carbon atoms.

According to another aspect of the present invention, there is provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one organic compound of the present invention.

According to the present invention, the organic electroluminescent compound represented by the formula [A] can be driven at a low voltage as compared with a conventional material, has excellent luminous efficiency, and can be used for the production of stable and excellent devices.

1 is a schematic view of an organic light emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail. In the drawings of the present invention, the sizes and dimensions of the structures are enlarged or reduced from the actual size in order to clarify the present invention, and the known structures are omitted so as to reveal the characteristic features, and the present invention is not limited to the drawings .

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings. In the following description, well-known functions or constructions are not described in detail to avoid obscuring the subject matter of the present invention.

It is to be understood that both the foregoing general description and the following detailed description of the present invention are exemplary and explanatory and are intended to provide further explanation of the invention as claimed. Respectively. In the drawings, for the convenience of explanation, the thicknesses of some layers and regions are exaggerated. It will be understood that when a layer, film, region, plate, or the like is referred to as being "on" another portion, it also includes the case where there is another portion in between.

Also, throughout the specification, when an element is referred to as "including" an element, it is understood that the element may include other elements as well, without departing from the other elements unless specifically stated otherwise. Also, throughout the specification, the term " on " means located above or below a target portion, and does not necessarily mean that the target portion is located on the upper side with respect to the gravitational direction.

The present invention provides a novel aromatic organic luminescent compound represented by the following formula (A) or (B).

(A)

[Chemical Formula B]

A1, A2, E and F are the same or different and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring, An aromatic heterocycle having 2 to 40 carbon atoms;

Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a condensed ring by forming a 5-membered ring with carbon atoms connected to the substituents R1 and R2;

The linking groups L1 to L4 are the same or different from each other, and each independently represents a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkinylene group having 2 to 60 carbon atoms, A substituted or unsubstituted alkylene group having 2 to 60 carbon atoms, an alkynylene group having 2 to 60 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 60 carbon atoms, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

M is any one selected from NR ₃ , CR ₄ R ₅ , SiR ₆ R ₇ , GeR ₈ R ₉ , O, S, Se;

The substituents R ₁ to R ₉ and Ar ₁ to Ar 4 are the same or different from each other and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms , A substituted or unsubstituted C 2 -C 30 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 3 -C 30 cycloalkyl group, a substituted or unsubstituted C 5 -C 30 A substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthio group, An alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms , A substituted or unsubstituted alkylgermanium group having 1 to 30 carbon atoms, a substituted or unsubstituted arylgermanium group having 1 to 30 carbon atoms, a cyano group, a nitro group, and a halogen group,

The carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be one of N, O, P, Si, S, Ge , Se, and Te;

Each of s1 to s4 is an integer of 1 to 3, and when each of them is 2 or more, each of the linking groups L1 to L4 is the same or different from each other,

X is an integer of 1 or 2, y and z are the same or different and independently of one another an integer of 0 to 3,

In the formula (A), two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) to form a condensed ring,

In the formula (B), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula (Q2) to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) ≪ / RTI >

The 'substituted' in the above 'substituted or unsubstituted' means a group selected from the group consisting of deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, , An alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms , An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, Group, and an aryloxy group having 1 to 24 carbon atoms.

In consideration of the range of the alkyl or aryl group in the above "substituted or unsubstituted alkyl group having 1 to 24 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 24 carbon atoms", it is preferable that the number of carbon atoms is 1 to 24 And the number of carbon atoms in the aryl group of 6 to 24 carbon atoms means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when it is considered that the substituent is not substituted without considering the substituted moiety. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having a carbon number of 4.

The aryl group, which is a substituent used in the compound of the present invention, is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and when the aryl group has a substituent, it is fused with neighboring substituents to further form a ring .

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m- terphenyl group, p- terphenyl group, naphthyl group, anthryl group, An aromatic group such as a phenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylenyle group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group, and at least one hydrogen atom of the aryl group may be substituted with a deuterium atom, a halogen atom (-NH ₂₎ , -NH (R), -N (R ') (R "), R' and R" are independently of each other an alkyl group having 1 to 10 carbon atoms A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms An alkenyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, An aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group, which is a substituent used in the compounds of the present invention, refers to a C 2 -C 24 ring aromatic system containing 1, 2 or 3 heteroatoms selected from N, O, P or S and the remaining ring atoms are carbon, The rings may be fused to form a ring. And at least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl and the like. The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, hexyloxy, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group used as the substituent in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, Butylsilyl, dimethylpurylsilyl and the like, and at least one hydrogen atom of the silyl group may be substituted with the same substituent as the aryl group.

The compound represented by the above formula (A) or (B) of the present invention has a structural characteristic in that when the formula (Q1) is connected to the ring (A2), the linking group (L2) comprising Ar2 is always bonded to the ring (A2) In the formula (B), when the structural formula Q2 is connected to the A1 ring and the structure Q1 is connected to the A2 ring, the A2 ring necessarily has a structural characteristic in which a linking group L2 including Ar2 is bonded.

In formula (A) or (B), A1, A2, E and F may be the same or different and independently of each other, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms.

As described above, when A1, A2, E and F in the formula (A) or the formula (B) are the same or different and independently of each other represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, The unsubstituted aromatic hydrocarbon rings having 6 to 50 carbon atoms may be the same or different and independently selected from [Structural Formula 10] to [Structural Formula 21].

[Structural formula 10] [Structural formula 11] [Structural formula 12]

[Structural Formula 13] [Structural Formula 14] [Structural Formula 15]

 [Structural formula 16] [Structural formula 17] [Structural formula 18]

[Structural formula 19] [Structural formula 20] [Structural formula 21]

In the above structural formulas 10 to 21, "- *" represents a 5-membered ring containing carbon connected to the substituents R ₁ and R ₂ , or a 5-membered ring containing M in the structural formulas Q 1 and Q 2 Means a binding site for forming a binding site,

When the aromatic hydrocarbon rings of the above-mentioned structural formulas 10 to 21 are bonded to the structural formula Q1 or the structural formula Q2 while being bonded to the A1 ring or the A2 ring, two adjacent carbon atoms are bonded to * of the above structural formula Q1 Or with a * of formula Q2 to form a condensed ring;

In the above Structural Formulas 10 to 21, R is the same as R1 and R2 defined above,

m is an integer of 1 to 8, and when m is 2 or more, or when R is 2 or more, each R may be the same or different from each other.

The linking groups L1 to L4 in the formulas (A) and (B) are each a single bond or any one selected from the following Structural Formulas 1 to 8, s1 to s4 are each 1 or 2, .

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural formula 5] [Structural formula 6] [Structural formula 7] [Structural formula 8]

The carbon position of the aromatic ring in the linking group may be bonded with hydrogen or deuterium.

Each of Ar1 to Ar4 is independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C50 aryl, substituted or unsubstituted C3 to C30 cycloalkyl, Or unsubstituted heteroaryl groups having 2 to 50 carbon atoms and substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, x and y in the above formulas (A) and (B) are each 1 and z is In this case, more specifically, Ar 2 may be a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.

In the present invention, the substituents R 1 and R 2 in the formula (A) or (B) may be the same or different and independently of each other, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms. In this case, each of the substituents R 1 and R 2 may be connected to each other to form a ring, or may not be connected to each other to form a ring.

Specific examples of the compound represented by the formula (A) or (B) in the present invention may be any one selected from the group consisting of the following formulas (1) to (138), but are not limited thereto.

&Lt; Formula 1 > < EMI ID =

&Lt; Formula 4 > < EMI ID =

&Lt; Formula 7 > < EMI ID =

&Lt; Formula 10 > < EMI ID =

&Lt; Formula 13 > < EMI ID =

&Lt; Formula 16 > < EMI ID =

&Lt; Formula 19 > < EMI ID =

&Lt; Formula 22 > < EMI ID =

&Lt; Formula 25 > < EMI ID = 26.0 >

&Lt; Formula 28 > < EMI ID = 29.0 >

&Lt; Formula 31 > < EMI ID =

&Lt; Formula 34 > < EMI ID =

&Lt; Formula 37 > < EMI ID = 38.0 >

&Lt; Formula 40 > < EMI ID =

&Lt; General Formula 43 >

&Lt; Formula 46 > < EMI ID =

&Lt; Formula 50 > < Formula 51 >

&Lt; Formula 52 >

&Lt; Formula 55 > < EMI ID = 56.0 >

<Formula 58> <Formula 59>

&Lt; Formula 61 > < EMI ID =

&Lt; Formula 64 > < EMI ID =

&Lt; Formula 67 >

<Formula 70> <Formula 71> <Formula 72>

&Lt; Formula 73 > < EMI ID =

&Lt; Formula 76 > < EMI ID =

&Lt; Formula 79 > < EMI ID =

<Formula 82> <Formula 83> <Formula 84>

&Lt; Formula 85 > < EMI ID =

&Lt; Formula 88 >

&Lt; Formula 91 > < EMI ID =

&Lt; Formula 94 > < EMI ID =

&Lt; Formula 97 >

&Lt; Formula 100 > < EMI ID =

&Lt; EMI ID = 103.1 >

(Formula 107) < EMI ID = 106.1 >

(110) < Formula (111) >

<Formula 112> <Formula 113> <Formula 114>

&Lt; Formula 115 > < EMI ID = 116.1 >

&Lt; EMI ID = 120.1 >

&Lt; Formula 121 > < EMI ID =

&Lt; Formula 124 > < EMI ID =

&Lt; Formula 127 >

[Formula 130] < EMI ID = 131.0 >

<Formula 133> <Formula 134> <Formula 135>

&Lt; EMI ID = 136.0 >

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one compound of the present invention.

In the present invention, "(organic layer) includes one or more compounds "," (organic layer) may include one kind of compound belonging to the scope of the present invention or two or more different compounds belonging to the category of the above compound Can be interpreted as "exist".

 At this time, the organic layer containing the compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.

In the present invention, the organic layer interposed between the first electrode and the second electrode may be a light emitting layer, wherein the light emitting layer is composed of a host and a dopant, and the compound represented by the formula (A) or (B) .

In this case, specific examples of the dopant substance used in the light emitting layer include a pyrene compound, a deuterium-substituted pyrene compound, an arylamine, a deuterium-substituted arylamine, a peryl compound, Substituted styryl compounds, starburst compounds, deuterium-substituted starburst compounds, deuterium-substituted styryl compounds, deuterium-substituted pyrrole-based compounds, hydrazone compounds, deuterated substituted hydrazone compounds, carbazole compounds, deuterated substituted carbazole compounds, stilbene compounds, Based compound, an oxadiazole-based compound, a deuterium-substituted oxadiazole-based compound, coumarine, deuterium-substituted coumarine, and the like, but the present invention is not limited thereto.

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

In the present invention, at least one layer selected from the functional layer having the hole injecting layer, the hole transporting layer, the hole injecting function and the hole transporting function, the light emitting layer, the electron transporting layer and the electron injecting layer may be formed by a deposition process or a solution process have.

Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each of the layers through heating or the like under vacuum or low pressure, Refers to a method of mixing a material used as a material with a solvent and forming the thin film by a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating or the like.

Further, the organic light emitting device of the present invention may be a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a single-color or white-colored flexible lighting device.

As a specific example of the present invention, a hole transport layer (HTL) is further stacked between the anode and the organic emission layer, and an electron transport layer (ETL) is added between the cathode and the organic emission layer . &Lt; / RTI &gt;

As the material of the hole transporting layer, electron-donating molecules having a small ionization potential are used, and diamine, triamine or tetraamine derivatives mainly having triphenylamine as a basic skeleton are widely used. For example, N, N'-bis (TPD) or N, N'-di (naphthalen-1-yl) -N, N (N, N'-diphenyl- '-Diphenylbenzidine (a-NPD) or the like can be used.

A hole injection layer (HIL) may be additionally formed on the lower portion of the hole transport layer. The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. For example, (4,4 ', 4 "-tri (N-carbazolyl) triphenylamine), m-MTDATA (4,4', 4" -tris- (3-methylphenylphenyl amino) triphenylamine) can be used.

As the material of the electron transporting layer, for example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

Meanwhile, an electron injection layer (EIL) may be further formed on the electron transport layer to facilitate injection of electrons from the cathode to ultimately improve power efficiency. The electron injection layer material As long as it is commonly used in the related art, it can be used without any particular limitation. For example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO can be used.

Hereinafter, the organic light emitting device of the present invention will be described with reference to FIG.

1 is a cross-sectional view showing a structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, And may further include an injection layer 70. In addition, one or two intermediate layers may be further formed.

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below. First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

In addition, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM, and the light emitting layer may be composed of a host and a dopant, and the compound of the present invention may be used as a host.

Here, the dopant may be a compound represented by the following formula (D1) or (D2). At this time, the light emitting layer may further include various dopant materials.

            [Chemical formula D1] [Chemical formula D2]

Among the above-mentioned structural formulas (D1) and (D2)

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, an optionally substituted arylene group having 6 to 60 carbon atoms , A substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having a hetero atom O, N or S, and the like.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms or a single bond, preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphthacene, Perylene, pentacene, and more particularly, the A may be a substituent represented by any one of the following formulas (A1) to (A10).

[Formula A1] [Formula A2] [Formula A3]

[Chemical Formula A4] [Chemical Formula A5] [Chemical Formula A6]

[Chemical formula A7] [Chemical formula A8] [Chemical formula A9]

(A10)

Wherein Z ₁ to Z ₂ in the formula [A3] are each independently selected from the group consisting of hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted Or an unsubstituted or substituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted aryl group having 2 to 60 carbon atoms (Substituted or unsubstituted C1-C60 alkyl) amino group, or a substituted or unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C60 alkylamino group, , (Substituted or unsubstituted aryl group having 6 to 60 carbon atoms) amino group, and Z ₁ to Z ₂ are the same or different from each other and can form a condensed ring with adjacent groups.

In the above formula (D1)

X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, X ₁ and X ₂ may be bonded to each other,

Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or a substituted or unsubstituted C1 to C24 heteroalkyl group, a substituted or unsubstituted C3 to C24 cycloalkyl group, a substituted or unsubstituted C1 to C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, and hydrogen. more selected species and, Y ₁ to Y ₂ each are the same or different each other, may form a fused ring group of the aliphatic, aromatic, aliphatic hetero, or aromatic heterocyclic group which are adjacent to each other It was.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula (D2)

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form, Each of which may be substituted with deuterium or alkyl, and may be the same as or different from each other.

In addition, Is a single bond or - [C (R ₅ ) (R ₆ )] _p -, and p is an integer of 1 to 3; when p is 2 or more, R ₅ and R ₆ are the same or different from each other;

Wherein _{R 1, R 2, R 3} , R 5 and R ₆ are, each independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Or beach (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, An aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron,

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and when R ₃ is plural, each R ₃ may be in fused form, and n is 1 to 4 It is an integer.

The amine group bonded to A in the above formulas [D1] and [D2] may be represented by any one selected from the group consisting of [substituents 1] to [52], but is not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3]

  [Substituent group 4] [Substituent group 5] [Substituent group 6]

[Substituent group 7] [Substituent group 8] [Substituent group 9]

 [Substituent group 10] [Substituent group 11] [Substituent group 12]

 [Substituent group 13] [Substituent group 14] [Substituent group 15]

 [Substituent group 16] [Substituent group 17] [Substituent group 18]

 [Substituent group 19] [Substituent group 20] [Substituent group 21]

 [Substituent group 22] [Substituent group 23] [Substituent group 24]

[Substituent group 25] [Substituent group 26] [Substituent group 27]

[Substituent group 28] [Substituent group 29] [Substituent group 30]

[Substituent group 31] [Substituent group 32] [Substituent group 33]

[Substituent group 34] [Substituent group 35] [Substituent group 36]

[Substituent group 37] [Substituent group 38] [Substituent group 39]

[Substituent group 40] [Substituent group 41] [Substituent group 42]

[Substituent group 43] [Substituent group 44] [Substituent group 45]

[Substituent group 46] [Substituent group 47] [Substituent group 48]

[Substituent group 49] [Substituent group 50] [Substituent group 51]

[Substituent 52]

In the above substituents, R may be the same or different from each other and is selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C1- A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted C1 to C60 alkoxy group, A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted aryl (having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, and each has 1 To 12 carbon atoms, and each of the substituents may form a condensed ring with adjacent groups.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

 (Example)

Synthesis Example 1: Synthesis of Formula 1

Synthesis of Synthesis Example 1- (1): [Intermediate 1-a]

[Intermediate 1-a] was synthesized according to Reaction Scheme 1 below.

<Reaction Scheme 1>

<Intermediate 1-a>

To a 500 mL round bottom flask reactor was added methyl 5-bromo-2-iodobenzoate (25.0 g, 73 mmol), 4-dibenzofuranboronic acid (18.7 g, 88 mmol), tetrakis (triphenylphosphine) palladium g, 0.15 mmol) and potassium carbonate (20.2 g, 146.7 mmol) were placed, and 125 mL of toluene, 125 mL of tetrahydrofuran, and 50 mL of water were added. The temperature of the reactor was raised to 80 ° C and stirred for 10 hours. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain Intermediate 1-a (75.0 g, 60.1%).

Synthesis Example 1- (2): Synthesis of Intermediate 1-b

Intermediate 1-b was synthesized according to Scheme 2 below:

<Reaction Scheme 2>

<Intermediate 1-a> <Intermediate 1-b>

<Intermediate 1-a> (17.0 g, 45 mmol), sodium hydroxide (2.14 g, 54 mmol) and 170 ml of ethanol were placed in a 500 mL round bottom flask reactor and refluxed for 48 hours. The reaction was terminated by thin film chromatography and then cooled to room temperature. 2-N HCl was added dropwise to the cooled solution, and the resulting solid was stirred for 30 minutes and filtered. Recrystallization from dichloromethane and n-hexane gave <Intermediate 1-b>. (14.5 g, 88.6%).

Synthesis Example 1- (3): Synthesis of Intermediate 1-c

Intermediate 1-c was synthesized according to scheme 3 below:

<Reaction Scheme 3>

<Intermediate 1-b> <Intermediate 1-c>

<Intermediate 1-b> (14.5 g, 39 mmol) and 145 ml of methanesulfonic acid were placed in a 250 ml round bottom flask reactor, and the mixture was heated to 80 ° C. and stirred for 3 hours. The reaction was terminated by thin film chromatography and then cooled to room temperature. The reaction solution was slowly added dropwise to 150 ml of ice water, followed by stirring for 30 minutes. The resulting solid was filtered and washed with water and methanol to give <Intermediate 1-c>. (11.50 g, 83.4%)

Synthesis Example 1- (4): Synthesis of Intermediate 1-d

Intermediate 1-d was synthesized according to Scheme 4 below:

<Reaction Scheme 4>

<Intermediate 1-c> <Intermediate 1-d>

<Intermediate 1-c> (11.5 g, 33 mmol) and 300 ml of dichloromethane were placed in a 1 L round bottom flask reactor, and the mixture was stirred at room temperature. Bromine (3.4 ml, 66 mmol) was added dropwise to 50 ml of dichloromethane, and the mixture was stirred at room temperature for 8 hours (11.0 g, 78%) was obtained by recrystallizing the solid from monochlorobenzene to obtain <Intermediate 1-d>. The reaction mixture was filtered and then washed with acetone.

Synthesis Example 1- (5): Synthesis of Intermediate 1-e

Intermediate 1-e was synthesized according to Scheme 5 below:

<Reaction Scheme 5>

<Intermediate 1-d> <Intermediate 1-e>

2-bromobiphenyl (8.4 g, 0.036 mol) and 110 ml of tetrahydrofuran were placed in a 250 ml round bottom flask reactor and cooled to -78 ° C in a nitrogen atmosphere. N-butyl lithium (19.3 ml, 0.031 mol) was added dropwise at the same temperature to the cooled reaction solution. The reaction solution was stirred for 2 hours, <Intermediate 1-d> (11.0 g, 0.026 mol) was added little by little and the mixture was stirred at room temperature. When the color of the reaction solution changed, the reaction was terminated by TLC. The reaction was completed by adding 50 ml of H 2 O and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and recrystallized from acetonitrile to obtain Intermediate 1-e. (12.2 g, 81.5%).

Synthesis Example 1- (6): Synthesis of Intermediate 1-f

Intermediate 1-f was synthesized according to Scheme 6 below:

<Reaction Scheme 6>

<Intermediate 1-e> <Intermediate 1-f>

<Intermediate 1-e> (12.0 g, 0.021 mol), 120 ml of acetic acid and 2 ml of sulfuric acid were placed in a 250 ml round-bottomed flask reactor and refluxed for 5 hours. When a solid was formed, the reaction was terminated by thin film chromatography and then cooled to room temperature. The resulting solid was filtered, washed with H2O and methanol, dissolved in monochlorobenzene, filtered through silica gel, concentrated and cooled to room temperature to obtain Intermediate 1-f. (10.7 g, 90% &gt;

Synthesis Example 1- (7): Synthesis of Compound (1)

Formula 1 was synthesized according to Scheme 7 below:

<Reaction Scheme 7>

&Lt; Intermediate 1-f > < EMI ID =

(10.0 g, 0.017 mol), phenylboronic acid (4.8 g, 0.039 mol), tetrakistriphenylphosphine palladium (0.8 g, 0.001 mol), potassium carbonate (9.56 g, 0.069 mol), 120 ml of toluene, 60 ml of ethanol and 45 ml of water were added and the mixture was refluxed and stirred for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature. The reaction solution was concentrated, dissolved in dichloromethane, recrystallized from methanol, and then hot-filtered with toluene. After separation and purification by column chromatography, recrystallization from dichloromethane and acetone yielded < Formula 1 &gt;. (9.9 g, 99%).

MS (MALDI-TOF): m / z 558.2 [M ^&lt; ⁺ &^gt;

Synthesis Example 2: Synthesis of Formula 21

Synthesis Example 2- (1): Synthesis of Intermediate 2-a

Intermediate 2-a was synthesized according to Scheme 8 below:

<Reaction Scheme 8>

<Intermediate 2-a>

1-Hydroxy 2-naphthalic acid (50 g, 266 mmol), methanol 1000 ml, and sulfuric acid 100 ml were placed in a 2 L round bottom flask reactor and refluxed with stirring for 100 hours. The reaction was terminated by TLC and then cooled to room temperature. The solution was concentrated under reduced pressure and then extracted with dichloromethane and water. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure, and recrystallized from heptane to obtain Intermediate 2-a. (39 g, 72.6%).

Synthesis Example 2- (2): Synthesis of Intermediate 2-b

Intermediate 2-b was synthesized according to Scheme 9 below:

<Reaction Scheme 9>

&Lt; Intermediate 2-a > < Intermediate 2-b &

<Intermediate 2-a> (39.0 g, 193 mmol) and 390 ml of acetic acid were placed in a 1 L round-bottom flask reactor and stirred at room temperature. Bromine (11.8 ml, 231 mmol) was added to 80 ml of acetic acid and added dropwise to the reaction solution. The reaction solution was stirred at room temperature for 5 hours. After completion of the reaction, the resulting solid was filtered, and <heptane slurry <Intermediate 2-b> was obtained. (50 g, 90%)

Synthesis Example 2- (3): Synthesis of Intermediate 2-c

Intermediate 2-c was synthesized according to Scheme 10 below:

<Reaction formula 10>

<Intermediate 2-b> <Intermediate 2-c>

<Intermediate 2-b> (50 g, 178 mmol) and dichloromethane were placed in a 2 L round bottom flask reactor and stirred. Pyridine (28.1 g, 356 mmol) was added to the reaction solution in a nitrogen atmosphere and stirred at room temperature for 20 minutes. The reaction solution was cooled to 0 ° C., and then trifluoromethane sulfonic anhydride (65.24 g, 231 mmol) was added dropwise in a nitrogen atmosphere. After stirring for 3 hours, the reaction was terminated by TLC, and 20 ml of water was added and stirred for 10 minutes. The reaction solution was concentrated under reduced pressure and then subjected to column separation to obtain <Intermediate 2-c>. (45 g, 61%).

Synthesis Example 2- (4): Synthesis of Intermediate 2-d

Intermediate 2-d was synthesized according to Scheme 11 below:

<Reaction Scheme 11>

<Intermediate 2-c> <Intermediate 2-d>

(45.0 g, 0.109 mol), 4-dibenzoylboronic acid (25.4 g, 0.120 mol), tetrakis (triphenylphosphine) palladium (2.5 g, 0.22 mmol) in a 1 L round bottom flask reactor, , Potassium carbonate (30.1 g, 0.218 mol), and 300 mL of toluene, 130 mL of ethanol and 90 mL of water were added. The temperature of the reactor was raised to 80 ° C and stirred for 5 hours. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <Intermediate 2-d>. (22.0 g, 46.1%).

Synthesis Example 2- (5): Synthesis of Intermediate 2-e

Intermediate 2-e was synthesized according to Scheme 12 below:

<Reaction Scheme 12>

<Intermediate 2-d> <Intermediate 2-e>

<Intermediate 2-d> (22.0, 0.051 mol) and sodium hydroxide (2.65 g, 0.066 mol) were placed in a 1 L round bottom flask reactor and refluxed for 48 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. 2-N HCl was added dropwise to the cooled solution, and the resulting solid was stirred for 30 minutes and filtered. Recrystallization from dichloromethane and n-hexane gave < intermediate 2-e >. (17.6 g, 82.7%)

Synthesis Example 2- (6): Synthesis of intermediate 2-f

Intermediate 2-f was synthesized according to Scheme 13 below:

<Reaction Scheme 13>

<Intermediate 2-e> <Intermediate 2-f>

<Intermediate 2-e> (17.6 g, 0.042 mol) and 170 ml of methanesulfonic acid were placed in a 500 ml round bottom flask reactor, and the mixture was heated to 80 ° C. and stirred for 3 hours. The reaction was terminated by thin film chromatography and then cooled to room temperature. The reaction solution was slowly added dropwise to 150 ml of ice water, followed by stirring for 30 minutes. The resulting solid was filtered and washed with water and methanol. The solid was dissolved in monochlorobenzene and filtered through a pad of silica gel. The filtrate was concentrated by heating and then recrystallized with acetone to obtain <Intermediate 2-f>. (12 g, 71%).

Synthesis Example 2- (7): Synthesis of Intermediate 2-g

Intermediate 2-g was synthesized according to Scheme 14 below:

<Reaction Scheme 14>

<Intermediate 2-f> <Intermediate 2-g>

<Intermediate 2-f> (12.0 g, 0.030 mol) and 360 ml of dichloromethane were placed in a 1 L round bottom flask reactor. Bromine (3.1 ml, 0.06 mol) was added dropwise to 40 ml of dichloromethane while stirring at room temperature. After stirring for 12 hours at room temperature, 100 ml of methanol was added, and the resulting solid was filtered and washed with methanol. Recrystallization from 1,2-dichlorobenzene and acetone gave <Intermediate 2-g>. (10.3 g, 71.7%).

Synthesis Example 2- (8): Synthesis of Intermediate 2-h

Intermediate 2-h was synthesized according to Scheme 15 below:

<Reaction Scheme 15>

<Intermediate 2-g> <Intermediate 2-h>

<Intermediate 2-h> was obtained using the same method except that <Intermediate 2-g> was used in place of <Intermediate 1-d> in Synthesis Example 1- (5). (10.0 g, 73.4%).

Synthesis Example 2- (9): Synthesis of Intermediate 2-i

Intermediate 2-i was synthesized according to Scheme 16 below:

<Reaction Scheme 16>

<Intermediate 2-h> <Intermediate 2-i>

<Intermediate 2-i> was obtained using the same method except that <Intermediate 2-h> was used in place of <Intermediate 1-e> in Synthesis Example 1- (6). (6.3 g, 64.8%).

Synthesis Example 2- (10): Synthesis of Compound (21)

(21) was synthesized according to Scheme 17 below:

<Reaction Scheme 17>

&Lt; Intermediate 2-i &

(Formula 21) was obtained by using the same method as in Synthesis Example 1- (7), except that <Intermediate 2-i> was used instead of <Intermediate 1-f>. (6.0 g, 98%).

MS (MALDI-TOF): m / z 608.21 [M ^&lt; ⁺ &^gt;].

Synthesis Example 3: Synthesis of Formula 34

Synthesis Example 3- (1): Synthesis of Intermediate 3-a

Intermediate 3-a was synthesized according to Scheme 18 below:

<Reaction Scheme 18>

<Intermediate 3-a>

A solution of 4-bromodibenzofuran (100.0 g, 0.405 mol), ethynyltrimethylsilane (47.7 g, 0.486 mol), [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (2.31 g, 0.012 mol), triphenylphosphine (10.6 g, 0.040 mol), and triethylamine (700 ml) were added and the mixture was stirred under reflux in a nitrogen atmosphere for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and 500 ml of heptane was added thereto. Celite and silica gel pad were laid and filtered. And concentrated under reduced pressure to obtain <Intermediate 3-a>. (130 g, 84%)

Synthesis Example 3- (2): Synthesis of Intermediate 3-b

Intermediate 3-b was synthesized according to Scheme 19 below:

<Reaction Scheme 19>

&Lt; Intermediate 3-a > < Intermediate 3-b &

<Intermediate 3-a> (130 g, 0.492 mol), potassium carbonate (101.9 g, 0.738 mol), 650 ml of methanol and 650 ml of tetrahydrofuran were placed in a 2 L round bottom flask reactor and stirred at room temperature for 2 hours. After completion of the reaction, 500 ml of heptane was added to complete the reaction. The reaction solution was filtered and the filtrate was extracted with ethyl acetate and water. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give oil <Intermediate 3-b>. (82 g, 84%).

Synthesis Example 3- (3): Synthesis of Intermediate 3-c

Intermediate 3-c was synthesized according to Scheme 20 below:

<Reaction Scheme 20>

<Intermediate 3-b> <Intermediate 3-c>

A solution of 2-bromobiphenyl (66.0 g, 0.283 mol), <intermediate 3-b> (65.3 g, 0.340 mol), [1,1'-bis (diphenylphosphino) ferrocene] Palladium (6.94 g, 0.008 mol), copper iodide (1.62 g, 0.008 mol), triphenylphosphine (7.4 g, 0.028 mol) and triethylamine (500 ml) were stirred under reflux in a nitrogen atmosphere for 5 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and 400 ml of heptane was added thereto. Celite and silica gel pad were laid and filtered. The filtrate was concentrated under reduced pressure and the resulting solid was filtered to obtain <Intermediate 3-c>. (80 g, 82%)

Synthesis Example 3- (4): Synthesis of Intermediate 3-d

Intermediate 3-d was synthesized according to Scheme 21 below:

<Reaction Scheme 21>

<Intermediate 3-c> <Intermediate 3-d>

<Intermediate 3-c> (80.0 g, 0.232 mol) was dissolved in 960 ml of dichloromethane in a 2 L round bottom flask reactor and cooled to -78 ° C. in a nitrogen atmosphere. To the cooled solution was added dropwise iodine monohydrate (278.4 ml, 0.279 mol) and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, a saturated sodium cyanosulfate aqueous solution was added and stirred. The mixture was extracted with dichloromethane and water, and the organic layer was separated and concentrated under reduced pressure. The crystals were collected with methanol to obtain <Intermediate 3-d>. (67 g, 61.3%).

Synthesis Example 3- (5): Synthesis of Intermediate 3-e

Intermediate 3-e was synthesized according to Scheme 22 below:

<Reaction Formula 22>

<Intermediate 3-d> <Intermediate 3-e>

   <Intermediate 3-d> (54.8 g, 0.117 mol) and 150 ml of tetrahydrofuran were placed in a 500 ml round-bottom flask reactor and cooled to -78 ° C. in a nitrogen atmosphere. To the cooled solution was added dropwise 1.6 molar n-butyllithium (62.4 ml, 0.1 mol) and the mixture was stirred at the same temperature for 1 hour. 9-Fluorenone (15.0 g, 0.083 mol) was dissolved in 50 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 8 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and water. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain oil <Intermediate 3-e>. (33.2 g, 76%).

Synthesis Example 3- (6): Synthesis of Intermediate 3-f

Intermediate 3-f was synthesized according to Scheme 23 below:

<Reaction Scheme 23>

<Intermediate 3-e> <Intermediate 3-f>

<Intermediate 3-e> (33.3 g, 0.063 mol), 330 ml of acetic acid and 3 ml of sulfuric acid were placed in a 1 L round bottom flask reactor and refluxed for 3 hours. The reaction was terminated by thin film chromatography and then cooled to room temperature. The resulting solid was filtered off and washed with H2O and methanol to give <Intermediate 3-f>. (28.6 g, 88% >

Synthesis Example 3- (7): Synthesis of Intermediate 3-g

Intermediate 3-g was synthesized according to Scheme 24 below:

<Reaction Scheme 24>

<Intermediate 3-f> <Intermediate 3-g>

<Intermediate 3-f> (20.0 g, 0.039 mol) and 200 ml of dichloromethane were dissolved in a 1 L round bottom flask reactor. While stirring at room temperature, bromine (6 ml, 0.118 mol) was diluted with 40 ml of dichloromethane and added dropwise. After stirring for 12 hours at room temperature, 100 ml of methanol was added, and the resulting solid was filtered and washed with methanol. The material was recrystallized from 1,2-dichlorobenzene and acetone to give < intermediate 3-g >. (16 g, 60%).

Synthesis Example 3- (8): Synthesis of Formula 34

According to Scheme 25, &lt; RTI ID = 0.0 &gt; 34 &lt; / RTI &

<Reaction Scheme 25>

&Lt; Intermediate 3-g > < EMI ID =

Was obtained in the same manner as in the synthesis example 1- (7) except that <intermediate 3-g> was used instead of <intermediate 1-f>. (5.2 g, 98.6%).

MS (MALDI-TOF): m / z 658.23 [M ^&lt; ⁺ &^gt;

Synthesis Example 4: Synthesis of Compound (52)

Synthesis Example 4- (1): Synthesis of Intermediate 4-a

Intermediate 4-a was synthesized according to Scheme 26 below:

<Reaction Scheme 26>

<Intermediate 4-a>

(20.0 g, 0.081 mmol), bis (pinacolato) diboron (26.7 g, 0.105 mol), [1,1'-bis (diphenylphosphino) ferrocene (1.3 g, 0.002 mol), potassium acetate (19.9 g, 0.202 mol) and 1,4-dioxane (200 ml) were added and the mixture was refluxed with stirring for 10 hours. After completion of the reaction, the celite pad was filtered. The filtrate was concentrated under reduced pressure, the column was separated, and recrystallized from dichloromethane and heptane to obtain <Intermediate 4-a>. (17.0 g, 70%)

Synthesis Example 4- (2): Synthesis of Intermediate 4-b

Intermediate 4-b was synthesized according to Scheme 27 below:

<Reaction Scheme 27>

&Lt; Intermediate 4-a > < Intermediate 4-b &

<Intermediate 4-b> was obtained using the same method except that <Intermediate 4-a> was used instead of 4-dibenzoylboronic acid in Synthesis Example 1- (1). (13.1 g, 68.9%).

Synthesis Example 4- (3): Synthesis of Intermediate 4-c

Intermediate 4-c was synthesized according to Scheme 28 below:

<Reaction Scheme 28>

<Intermediate 4-b> <Intermediate 4-c>

<Intermediate 4-c> was obtained using the same method except that Intermediate 4-b was used instead of Intermediate 1-a in Synthesis Example 1- (2). (11.0 g, 87%).

Synthesis Example 4- (4): Synthesis of Intermediate 4-d

Intermediate 4-d was synthesized according to Scheme 29 below:

<Reaction Scheme 29>

<Intermediate 4-c> <Intermediate 4-d>

<Intermediate 4-d> was obtained (11.0 g, 87%) except that <Intermediate 4-c> was used in place of <Intermediate 1-b> in Synthesis Example 1- (3)

Synthesis Example 4- (5): Synthesis of Intermediate 4-e

Intermediate 4-e was synthesized according to Scheme 30 below:

<Reaction Scheme 30>

<Intermediate 4-d> <Intermediate 4-e>

Intermediate 4-e> (6.7 g, 60.7%) was obtained using the same method except that Intermediate 4-d was used instead of Intermediate 1-c in Synthesis Example 1- (4)

Synthesis Example 4- (6): Synthesis of Intermediate 4-f

Intermediate 4-f was synthesized according to Scheme 31 below:

<Reaction Scheme 31>

<Intermediate 4-e> <Intermediate 4-f>

<Intermediate 4-f> was obtained (5.2 g, 55%) except that Intermediate 4-e was used instead of Intermediate 1-d in Synthesis Example 1- (5)

Synthesis Example 4- (7): Synthesis of Intermediate 4-g

Intermediate 4-g was synthesized according to Scheme 32 below:

<Reaction equation 32>

<Intermediate 4-f> <Intermediate 4-g>

<Intermediate 4-g> was obtained using the same method except that <Intermediate 4-f> was used in place of <Intermediate 1-e> in Synthesis Example 1- (6). (4.3 g, 85.3%).

Synthesis Example 4- (8): Synthesis of Compound (52)

(52) was synthesized according to Scheme 33 below:

<Reaction Scheme 33>

&Lt; Intermediate 4-g &

(52) was obtained in the same manner as in Synthesis Example 1- (7), except that <Intermediate 4-g> was used instead of <Intermediate 1-f>. (2.5 g, 34%).

MS (MALDI-TOF): m / z 558.2 [M ^&lt; ⁺ &^gt;

Synthesis Example 5: Synthesis of Compound (83)

Synthesis Example 5- (1): Synthesis of Intermediate 5-a

Intermediate 5-a was synthesized according to Scheme 34 below:

<Reaction formula 34>

<Intermediate 5-a>

2-Phenoxyaniline (25.0, 0.135 mol), 30 ml of hydrochloric acid and 150 ml of water were added to a 1 L round bottom flask reactor, and the mixture was cooled to 0 ° C and stirred for 1 hour. 75 ml of an aqueous solution of sodium nitrite (11.2 g, 0.162 mol) was added dropwise to the reaction solution at the same temperature, followed by stirring for 1 hour. When 75 ml of an aqueous solution of potassium iodide (44.8 g, 0.270 mol) was added dropwise, the temperature of the reaction solution was dropped so as not to exceed 5 ° C. After stirring for 5 hours at room temperature, the reaction mixture was washed with an aqueous solution of sodium cyanosulfate and extracted with ethyl acetate and water. The organic layer was separated and concentrated under reduced pressure, followed by separation and purification by column chromatography to obtain <Intermediate 5-a>. (22.6 g, 56.5%).

Synthesis Example 5- (2): Synthesis of Intermediate 5-b

Intermediate 5-b was synthesized according to Scheme 35 below:

<Reaction Scheme 35>

<Intermediate 1-d> <Intermediate 5-a> <Intermediate 5-b>

<Intermediate 5-b> was obtained using the same method except that <Intermediate 5-a> was used instead of 2-bromobiphenyl in Synthesis Example 1- (5). (19.6 g, 70.4%)

Synthesis Example 5- (3): Synthesis of Intermediate 5-c

Intermediate 5-c was synthesized according to Scheme 36 below:

<Reaction Formula 36>

<Intermediate 5-b> <Intermediate 5-c>

<Intermediate 5-c> was obtained using the same method except that Intermediate 5-b was used instead of Intermediate 1-e in Synthesis Example 1- (6). (14.2 g, 74.7%).

Synthesis Example 5- (4): Synthesis of Compound (83)

According to Scheme 37, &lt; RTI ID = 0.0 &gt; 83 &lt; / RTI &

(Reaction Scheme 37)

&Lt; Intermediate 5-c >

Was obtained in the same manner as in the synthesis example 1- (7), except that <Intermediate 5-c> was used instead of <Intermediate 1-f>. (2.4 g, 28%).

MS (MALDI-TOF): m / z 574.19 [M ^&lt; ⁺ &^gt;

Synthesis Example 6: Synthesis of Compound (104)

Synthesis Example 6- (1): Synthesis of Intermediate 6-a

Intermediate 6-a was synthesized according to Scheme 38 below:

<Reaction Formula 38>

<Intermediate 6-a>

4-dibenzoylboronic acid (85.0 g, 0.401 mol), bismuth (III) nitrate pentahydrate (99.2 g, 0.200 mol) and 400 ml of toluene were placed in a 2 L round bottom flask reactor and stirred at 70 ° C for 3 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to room temperature and the resulting solid was filtered. After washing with toluene, <Intermediate 6-a> was obtained. (61.5 g, 72%)

Synthesis Example 6- (2): Synthesis of Intermediate 6-b

Intermediate 6-b was synthesized according to Scheme 39 below:

<Reaction Scheme 39>

&Lt; Intermediate 6-a > < Intermediate 6-b &

A 2 L round bottom flask reactor was charged with ethyl cyanoacetate (202.9 g, 1.794 mol) and dimethylformamide (500 mL). Potassium hydroxide (67.10 g, 1.196 mol) and potassium cyanide (38.95 g, 0.598 mol) were added, and dimethylformamide (200 ml) was added and the mixture was stirred at room temperature. <Intermediate 6-a> (127.5 g, 0.737 mol) was gradually added to the reaction solution and stirred at 50 ° C. for 72 hours. After completion of the reaction, 200 ml of an aqueous solution of sodium hydroxide (25%) was added and the mixture was stirred under reflux. After stirring for 3 hours, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and purified by column chromatography to obtain <Intermediate 6-b>. (20.0 g, 16%).

Synthesis Example 6- (3): Synthesis of Intermediate 6-c

Intermediate 6-c was synthesized according to Scheme 40 below:

<Reaction formula 40>

<Intermediate 6-b> <Intermediate 6-c>

<Intermediate 6-b> (20.0 g, 0.096 mol), 600 ml of ethanol and 170 ml of an aqueous solution of potassium hydroxide (142.26 g, 2.53 mol) were placed in a 2 L round bottom flask reactor and refluxed and stirred for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature. To the reaction solution, 400 ml of 6N HCl was added and acidified. The resulting solid was stirred for 20 minutes and then filtered. The solid was washed with ethanol and then <Intermediate 6-c> was obtained. (17.0 g, 88.5%).

Synthesis Example 6- (4): Synthesis of Intermediate 6-d

Intermediate 6-d was synthesized according to scheme 41 below:

<Reaction Scheme 41>

<Intermediate 6-c> <Intermediate 6-d>

<Intermediate 6-c> (17.0 g, 0.075 mol) and 15 ml of sulfuric acid were placed in a 2 L round-bottom flask reactor and refluxed for 72 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated and washed with aqueous sodium hydrogencarbonate solution. The organic layer was excessively loaded with methanol under reduced pressure, and the resulting solid was filtered to obtain <Intermediate 6-d>. (14.0 g, 77.6%).

Synthesis Example 6- (5): Synthesis of Intermediate 6-e

Intermediate 6-e was synthesized according to scheme 42 below:

<Reaction Scheme 42>

<Intermediate 6-d> <Intermediate 6-e>

<Intermediate 6-e> was obtained using the same method except that <Intermediate 6-d> was used instead of 2-phenoxyaniline in the above Synthesis Example 5- (1). (9.1 g, 48%)

Synthesis Example 6- (6): Synthesis of Intermediate 6-f

Intermediate 6-f was synthesized according to scheme 43 below:

<Reaction Scheme 43>

<Intermediate 6-e> <Intermediate 4-a> <Intermediate 6-f>

<Intermediate 6-f> was obtained using the same method as in Synthesis Example 4- (2), except that <Intermediate 6-e> was used instead of methyl 5-bromo-2-iodobenzoate. (5.3 g, 52.3%).

Synthesis Example 6- (7): Synthesis of Intermediate 6-g

Intermediate 6-g was synthesized according to Scheme 44 below:

<Reaction Scheme 44>

<Intermediate 6-f> <Intermediate 6-g>

<Intermediate 6-g> was obtained using the same method except that <Intermediate 6-f> was used in place of <Intermediate 1-a> in Synthesis Example 1- (2). (4.5 g, 88.1%).

Synthesis Example 6- (8): Synthesis of Intermediate 6-h

Intermediate 6-h was synthesized according to Scheme 45 below:

<Reaction Scheme 45>

<Intermediate 6-g> <Intermediate 6-h>

<Intermediate 6-h> was obtained using the same method except that <Intermediate 6-g> was used in place of <Intermediate 1-b> in Synthesis Example 1- (3). (3.8 g, 88.8%).

Synthesis Example 6- (9): Synthesis of Intermediate 6-i

Intermediate 6-i was synthesized according to Scheme 46 below:

<Reaction Formula 46>

<Intermediate 6-h> <Intermediate 6-i>

<Intermediate 6-i> was obtained (3 g, 55%) except that Intermediate 6-h was used instead of Intermediate 1-c in Synthesis Example 1- (4)

Synthesis Example 6- (10): Synthesis of Intermediate 6-j

Intermediate 6-j was synthesized according to Scheme 47 below:

<Reaction Scheme 47>

<Intermediate 6-i> <Intermediate 6-j>

<Intermediate 6-j> was obtained using the same method except that Intermediate 6-i was used instead of Intermediate 1-d in Synthesis Example 1- (5). (2.5 g, 64%).

Synthesis Example 6- (10): Synthesis of intermediate 6-k

Intermediate 6-k was synthesized according to Scheme 48 below:

<Reaction Scheme 48>

<Intermediate 6-j> <Intermediate 6-k>

<Intermediate 6-k> was obtained using the same method except that Intermediate 6-j was used instead of Intermediate 1-e in Synthesis Example 1- (6). (2.2 g, 90.4%)

Synthesis Example 6- (11): Synthesis of Formula 104

104 was synthesized according to Scheme 49 below:

<Reaction Scheme 49>

<중간체 6-k> <화학식 104>

<Intermediate 6-k>

(10.0 g, 0.015), 2-naphthalene boronic acid (5.16 g, 0.030 mol), tetrakistriphenylphosphine palladium (0.706 g, 0.001 mol), potassium carbonate , 45 ml of toluene, 45 ml of dioxane and 18 ml of water were added, and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature. The reaction solution was concentrated, dissolved in dichloromethane, recrystallized from methanol, and then hot-filtered with toluene. The separated and purified by column chromatography, and then recrystallized from dichloromethane and acetone to obtain < Formula 104 &gt;. (8.6 g, 77%).

MS (MALDI-TOF): m / z 748.24 [M ^&lt; ⁺ &^gt;].

Synthesis Example 7: Synthesis of Formula 115

Synthesis Example 7- (1): Synthesis of Intermediate 7-a

Intermediate 7-a was synthesized according to scheme 50 below:

<Reaction Formula 50>

<Intermediate 7-a>

4-dibenzoylboronic acid (85.0 g, 0.401 mol), bismuth (III) nitrate pentahydrate (99.2 g, 0.200 mol) and 400 ml of toluene were placed in a 2 L round bottom flask reactor and stirred at 70 ° C for 3 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to room temperature and the resulting solid was filtered. After washing with toluene, <Intermediate 7-a> was obtained. (61.5 g, 72%)

Synthesis Example 7- (2): Synthesis of Intermediate 7-b

Intermediate 7-b was synthesized according to scheme 51 below:

<Reaction Scheme 51>

<Intermediate 7-a> <Intermediate 7-b>

A 2 L round bottom flask reactor was charged with ethyl cyanoacetate (202.9 g, 1.794 mol) and dimethylformamide (500 mL). Potassium hydroxide (67.10 g, 1.196 mol) and potassium cyanide (38.95 g, 0.598 mol) were added, and dimethylformamide (200 ml) was added and the mixture was stirred at room temperature. <Intermediate 7-a> (127.5 g, 0.737 mol) was gradually added to the reaction solution and stirred at 50 ° C. for 72 hours. After completion of the reaction, 200 ml of an aqueous solution of sodium hydroxide (25%) was added and the mixture was stirred under reflux. After stirring for 3 hours, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and purified by column chromatography to obtain <Intermediate 7-b>. (20.0 g, 16%).

Synthesis Example 7- (3): Synthesis of Intermediate 7-c

Intermediate 7-c was synthesized according to scheme 52 below:

<Reaction Scheme 52>

<Intermediate 7-b> <Intermediate 7-c>

<Intermediate 7-b> (20.0 g, 0.096 mol), 600 ml of ethanol and 170 ml of an aqueous solution of potassium hydroxide (142.26 g, 2.53 mol) were placed in a 2 L round bottom flask reactor and refluxed and stirred for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature. The reaction solution was acidified with 400 ml of hexane hydrochloric acid, and the resulting solid was stirred for 20 minutes and then filtered. After washing with ethanol, <Intermediate 7-c> was obtained. (17.0 g, 88.5%).

Synthesis Example 7- (4): Synthesis of Intermediate 7-d

Intermediate 7-d was synthesized according to Scheme 53 below:

<Reaction Scheme 53>

<Intermediate 7-c> <Intermediate 7-d>

<Intermediate 7-c> (17.0 g, 0.075 mol) and 15 ml of sulfuric acid were placed in a 2 L round-bottom flask reactor and refluxed for 72 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated and washed with aqueous sodium hydrogencarbonate solution. Methanol was added in excess while concentrating under reduced pressure, and the resulting solid was filtered to obtain <Intermediate 7-d>. (14.0 g, 77.6%).

Synthesis Example 7- (5): Synthesis of Intermediate 7-e

Intermediate 7-e was synthesized according to scheme 54 below:

<Reaction Scheme 54>

<Intermediate 7-d> <Intermediate 7-e>

<Intermediate 7-e> was obtained using the same method except that <Intermediate 7-d> was used instead of 2-phenoxyaniline in the above Synthesis Example 5- (1). (9.1 g, 48%)

Synthesis Example 7- (6): Synthesis of Intermediate 7-f

Intermediate 7-f was synthesized according to the following scheme 55:

<Reaction Scheme 55>

<Intermediate 7-e> <Intermediate 4-a> <Intermediate 7-f>

<Intermediate 7-e> was used in place of methyl 5-bromo-2-iodobenzoate in Synthesis Example 1- (1), and <Intermediate 4-a> was used in place of 4-dibenzofuranboronic acid. <Intermediate 7-f> was obtained using the same method. (5.3 g, 52.3%).

Synthesis Example 7- (7): Synthesis of Intermediate 7-g

Intermediate 7-g was synthesized according to scheme 56 below:

<Reaction Scheme 56>

<Intermediate 7-f> <Intermediate 7-g>

<Intermediate 7-g> was obtained using the same method except that <Intermediate 7-f> was used in place of <Intermediate 1-a> in Synthesis Example 1- (2). (4.5 g, 88.1%).

Synthesis Example 7- (8): Synthesis of Intermediate 7-h

Intermediate 7-h was synthesized according to Scheme 57 below:

<Reaction Scheme 57>

<Intermediate 7-g> <Intermediate 7-h>

<Intermediate 7-h> was obtained using the same method except that Intermediate 7-g was used instead of Intermediate 1-b in Synthesis Example 1- (3). (3.8 g, 88.8%).

Synthesis Example 7- (9): Synthesis of Intermediate 7-i

Intermediate 7-i was synthesized according to Scheme 58 below:

<Reaction Scheme 58>

<Intermediate 7-h> <Intermediate 7-i>

<Intermediate 7-i> was obtained using the same method except that Intermediate 7-h was used instead of Intermediate 1-c in Synthesis Example 1- (4). (3.0 g, 55%).

Synthesis Example 7- (10): Synthesis of Intermediate 7-j

Intermediate 7-j was synthesized according to Scheme 59 below:

<Reaction Scheme 59>

<Intermediate 7-i> <Intermediate 7-j>

<Intermediate 7-j> was obtained (2.5 g, 64%) except that <Intermediate 7-i> was used in place of <Intermediate 1-d> in Synthesis Example 1- (5)

Synthesis Example 7- (10): Synthesis of Intermediate 7-k

Intermediate 7-k was synthesized according to scheme 60 below:

<Reaction Scheme 60>

<Intermediate 7-j> <Intermediate 7-k>

<Intermediate 7-k> was obtained using the same method except that Intermediate 7-j was used instead of Intermediate 1-e in Synthesis Example 1- (6). (2.2 g, 90.4%)

Synthesis Example 7- (11): Synthesis of Compound (115)

(115) was synthesized according to Scheme 61: &lt; RTI ID = 0.0 &gt;

<Reaction Scheme 61>

&Lt; Intermediate 7-k &

(10.0 g, 0.015 mol), indole (3.9 g, 0.033 mol), tri-tertiary-butylphosphonium tetrafluoroborate (1.4 g, 0.002 mol), phosphonium (0.887 g, 0.003 mol), sodium tertiary butoxide (8.45 g, 0.061 mol) and xylene (50 ml) were added and stirred under reflux for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. Concentrated, recrystallized from methanol and hot filtered with toluene. After separation and purification by column chromatography, recrystallization from dichloromethane and acetone yielded < 115 &gt;. (8.9 g, 81.5%).

MS (MALDI-TOF): m / z 726.23 [M ^&lt; ⁺ &^gt;].

Examples 1 to 7: Preparation of organic light emitting device

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the ITO glass in the vacuum chamber, the base pressure 1 × 10 ^- to and then after that the ⁷ torr formed by DNTPD (700 Å), α- NPD (300 Å) in order on the ITO present in Table 1 (E-1) and (E-2) in an electron transporting layer at a ratio of 1: 1 as an electron transporting layer to 300 Å , And an electron injecting layer (E-1) of 5 Å and Al (1000 Å) in this order. Thus, an organic light emitting device was manufactured. The luminescent characteristics of the organic light emitting device were measured at 0.4 mA.

            [DNTPD] [[alpha] -NPD]

[BD1] [Formula E-1] [Formula E-2]

Comparative Example 1

Except for using [BH1] as a host instead of the compound used in Examples 1 to 7, organic light emitting devices were fabricated in the same manner, and the luminescent characteristics of the organic light emitting devices were measured at 0.4 mA. The structure of [BH1] is as follows.

         [BH1]

The voltage, the current density, the Q.E, and the color coordinates were measured for the organic light-emitting devices manufactured according to Examples 1 to 7 and Comparative Example 1, and the results are shown in Table 1 below.

Voltage Current density
(mA / cm ² ) Q.E (%) CIEx CIEy Comparative Example 1
[BH1] 4.1 10 5.2 0.143 0.150 Example 1
[Chemical Formula 1] 3.5 10 5.9 0.135 0.140 Example 2
[Chemical Formula 21] 3.7 10 7.7 0.137 0.146 Example 3
(34) 3.8 10 8.6 0.135 0.146 Example 4
(52) 3.3 10 7.5 0.140 0.148 Example 5
(83) 3.7 10 7.2 0.135 0.143 Example 6
&Lt; EMI ID = 3.6 10 8 0.137 0.141 Example 7
(115) 3.8 10 6.7 0.132 0.148

As shown in Table 1, the compound according to the present invention has higher efficiency (QE) than that of the compound of Comparative Example 1 according to the prior art and can exhibit excellent device characteristics for driving at a low voltage, .

Claims (10)

A compound represented by the following formula (B).
[Chemical Formula B]

Wherein A1, A2, E and F are the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms;
Two carbon atoms adjacent to each other in the aromatic ring of A1 and two carbon atoms adjacent to each other in the aromatic ring of A2 form a condensed ring by forming a 5-membered ring with carbon atoms connected to the substituents R1 and R2;
The linking groups L1 and L2 are the same or different from each other and independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;
M is any one selected from O and S;
The substituents R ₁ and R ₂ are the same or different from each other and are independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, A substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,
In the case where R ₁ or R ₂ is an aryl group having 6 to 24 carbon atoms substituted, the substituent is selected from deuterium, a halogen group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, and an alkylsilyl group having 1 to 24 carbon atoms Which is selected,
R 1 and R 2 may be connected to each other to form a monocyclic or polycyclic ring of alicyclic or aromatic,
The substituted or unsubstituted C6-C50 aryl group, the substituted or unsubstituted C3-C30 cycloalkyl group, the substituted or unsubstituted C1-C30 alkyl group, the substituted or unsubstituted C1- And a heteroaryl group having 2 to 50 carbon atoms,
Ar 2 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms,
S1 and s2 are each an integer of 1 to 3, and when each of them is 2 or more, each of the linking groups L1 and L2 is the same or different from each other,
X and y are each 1, z is 0,
In the formula (B), two carbon atoms adjacent to each other in the A1 ring are bonded to * in the formula (Q2) to form a condensed ring, and two carbon atoms adjacent to each other in the A2 ring are bonded to * in the formula (Q1) &Lt; / RTI &gt;
The 'substituted' in the 'substituted or unsubstituted' is a group selected from the group consisting of deuterium, a halogen group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, , An alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 6 to 24 carbon atoms. The method according to claim 1,
The substituted or unsubstituted aromatic hydrocarbon rings in A1, A2, E and F are the same or different and are each independently selected from the group consisting of Structural Formulas 10 to 21 .
[Structural formula 10] [Structural formula 11] [Structural formula 12]

[Structural Formula 13] [Structural Formula 14] [Structural Formula 15]

[Structural formula 16] [Structural formula 17] [Structural formula 18]

[Structural formula 19] [Structural formula 20] [Structural formula 21]

In the above structural formulas 10 to 21, "- *" represents a 5-membered ring containing carbon connected to the substituents R ₁ and R ₂ , or a 5-membered ring containing M in the structural formulas Q 1 and Q 2 Means a binding site for forming a binding site,
When the aromatic hydrocarbon rings of the above-mentioned structural formulas 10 to 21 are bonded to the structural formula Q1 or the structural formula Q2 while being bonded to the A1 ring or the A2 ring, two adjacent carbon atoms are bonded to * of the above structural formula Q1 Or with a * of formula Q2 to form a condensed ring;
In the above-mentioned structural formulas 10 to 21, R is the same as R 1 and R 2 defined in claim 1,
m is an integer of 1 to 8, and when m is 2 or more, or when R is 2 or more, each R may be the same or different from each other. The method according to claim 1,
The linking groups L1 and L2 in the above formula (B) are each a single bond or any one selected from the following [structural formula 1], [structural formula 2], [structural formula 4], [structural formula 6], [structural formula 7]
s1 and s2 are each 1 or 2.
[Structural formula 1] [Structural formula 2] [Structural formula 4]

[Structural formula 6] [Structural formula 7]

The carbon position of the aromatic ring in the linking group may be bonded with hydrogen or deuterium. The method according to claim 1,
And R &lt; 2 &gt; in the formula (B) are the same or different and independently of each other, an unsubstituted aryl group having 6 to 24 carbon atoms. The method according to claim 1,
The above compound is obtained by reacting a compound represented by the following general formula (28) to (32), (76) to (79), [Formula 81], [Formula 91], [Formula 92], [Formula 96] Is any one selected from the group consisting of the following formulas (117), (120) to (123), (127) to (129), (134)
&Lt; Formula 28 >< EMI ID = 29.0 >

&Lt; Formula 31 >< EMI ID =

&Lt; Formula 77 &gt;&lt; EMI ID =

&Lt; Formula 81 >< EMI ID =

&Lt; EMI ID =

&Lt; Formula 105 >< EMI ID =

<Formula 108><Formula109>

&Lt; Formula 111 &gt;&lt; EMI ID =

&Lt; Formula 114 >

&Lt; EMI ID = 120.1 >

&Lt; Formula 122 >< EMI ID =

&Lt; Formula 128 &gt;&lt; EMI ID =

&Lt; Formula 135 >< EMI ID = 136.0 >

&Lt; EMI ID =

A first electrode;
A second electrode facing the first electrode; And
And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises at least one compound selected from the group consisting of the compounds represented by any one of claims 1 to 5. The method according to claim 6,
Wherein the organic layer comprises at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, and an electron injecting layer. 8. The method of claim 7,
Wherein the organic layer interposed between the first electrode and the second electrode is a light emitting layer, and the light emitting layer comprises a host and a dopant, and the compound is used as a host. 8. The method of claim 7,
Wherein at least one layer selected from the respective layers is formed by a deposition process or a solution process. The method according to claim 6,
The organic light emitting device includes a flat panel display device; A flexible display device; Monochrome or white flat panel illumination devices; And a device for flexible illumination of a single color or a white color.

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