KR102215780B1 - Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same - Google Patents

Abstract

[화학식 B]

The present invention relates to an organic light-emitting compound and an organic light-emitting device including the same, represented by the following [Formula A] or [Formula B], substituents A1 to A4, R ₁ to R ₁₆ , L1, L2, X, m, n, n'and p are the same as defined in the detailed description of the invention.
[Formula A]

[Formula B]

Description

Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same}

The present invention relates to a novel organic compound and an organic light-emitting device including the same, and in more detail, a novel organic compound capable of lowering a driving voltage and showing device characteristics excellent in luminous efficiency, and an organic light-emitting device including the same It relates to the device.

Recently, as display devices have become larger, there is an increasing demand for display devices that occupy less space or bendable display devices due to a flat panel structure, and liquid crystal displays, which are representative flat display devices, are lighter than conventional CRT (cathode ray tubes). Although there is an advantage that it is possible, it has disadvantages such as a limited viewing angle and a need for back light. On the other hand, organic light emitting diodes (OLEDs), which are new flat display devices, are displays using a self-luminous phenomenon, and have advantages such as a large viewing angle, lightness and compactness compared to liquid crystal displays, and fast response speed. And, in recent years, applications to full-color displays or lighting are expected.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.

An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground. These organic light-emitting devices are known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

Materials used as the organic material layer in the organic light-emitting device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. The light-emitting material may be classified into a high-molecular-type and a low-molecular-type according to its molecular weight, and may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emitting mechanism . In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum light-emitting wavelength shifts to a long wavelength due to the interaction between molecules, and the color purity decreases, or the efficiency of the device decreases due to the light-emitting attenuation effect. In order to increase the luminous efficiency through transition, a host-dopant system may be used as a light emitting material.

The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, 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 moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

In order for the organic light-emitting device to fully exhibit the above-described excellent features, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc., are supported by stable and efficient materials. Things must precede.

When an electric current is applied to the organic light emitting device, holes and electrons are injected from the anode and the cathode, respectively, and the injected holes and electrons are recombined in the emission layer through the respective hole transport layer and electron transport layer to form emission excitons. The light-emitting excitons thus formed emit light while transitioning to the ground state. The light may be divided into fluorescence using singlet excitons and phosphorescence using triplet excitons according to an emission mechanism, and the fluorescence and phosphorescence may be used as a light emitting source of an organic light emitting device.

On the other hand, fluorescence using only singlet excitons has a 25% probability of occurrence of singlet excitons, so there is a limit to the luminous efficiency, whereas phosphorescence that can use triplet excitons has superior luminous efficiency compared to fluorescence. Is going on.

CBP is the most widely known host material of the phosphorescent emitter so far, and an organic light emitting device to which a hole blocking layer such as BCP and BAlq is applied is known.

However, a device using a conventional phosphorescent material is more efficient than a device using a fluorescent material, but in the case of a conventional material such as BAlq or CBP used as a host of a phosphorescent material, the driving voltage is higher than that of a device using a fluorescent material. As it is high, there is no big advantage in terms of power efficiency (lm/w), and there are disadvantages that are not satisfactory in terms of lifespan. In addition, in order to use such a phosphorescent material as a light-emitting device, Korean Patent Publication No. 10-2011-0013220 (2011.02.09) discloses an aromatic heterocycle in the skeleton of a 6-membered aromatic ring or a 6-membered heteroaromatic ring. Introduced organic compounds are described, and Japanese Laid-Open Patent Publication No. 2010-166070 (2010.7.29) describes organic compounds in which an aryl or heteroaryl ring is bonded to a substituted or unsubstituted pyrimidine or quinazoline skeleton. Has been.

However, despite the efforts to manufacture the material for an organic light-emitting device as described above, it is not yet sufficient to develop materials for low driving voltage and high luminous efficiency, so that it is possible to drive at low voltage and has excellent luminous efficiency. The necessity of developing a light emitting material is a situation that is continuously required.

Patent Publication No. 10-2011-0013220 (2011.02.09)

Japanese Unexamined Patent Application Publication No. 2010-166070 (2010.7.29)

Accordingly, the first technical problem to be achieved by the present invention is to provide a novel organic compound that can be used in an emission layer of an organic light emitting device, has a long lifespan, low voltage driving characteristics, and excellent luminous efficiency.

A second technical problem to be achieved by the present invention is to provide an organic light-emitting device including the organic compound.

The present invention provides a compound represented by the following [Chemical Formula A] or [Chemical Formula B] in order to achieve the first technical problem.

[Formula A]

[Formula B]

In the [Formula A] or [Formula B],

The A ₁ to A ₄ and R ₁ to R ₁₆ are each the same or different, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms , A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon number of 5 to 30 Cycloalkenyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted An arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted arylamine group having O, N or S as a hetero atom It is any one selected from a C2-C50 heteroaryl group, a cyano group, a nitro group, and a halogen group, and the A ₁ to A ₄ and R ₁ to R ₈ are each connected with a substituent adjacent to each other to be an alicyclic, aromatic Can form a monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, and O ;

The L ₁ and L ₂ is a linking group, a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted C 2 to C 60 Alkenylene group, substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, substituted or unsubstituted C3 to C60 A cycloalkylene group, 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;

X is a linking group, or a single bond or -C(R ₃₁ R ₃₂ )-, NR ₃₃ , O, S, SiR ₃₄ R ₃₅ , GeR ₃₆ R ₃₇ , PR ₃₈ , PR ₃₉ (=O), C=O, BR ₄₀ Is,

R ₃₁ to R ₄₀ are the same as defined in R ₁ to R ₁₆ ;

The m, n, n'and p are each independently an integer of 1 to 3,

When m, n, n'and p are each 2 or more, each linking group and indole group are the same or different from each other;

In formula A, p of R ₅ to R ₈ and R ₁₀ to R _{13 ,} R ₁₅ and R ₁₆ One of each is a single bond connected to the L ₂ ,

In Formula B, p of R ₅ to R ₈ is a single bond connected to L ₂ .

In addition, the present invention includes a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, and the organic layer is It provides an organic light-emitting device comprising at least one organic light-emitting compound of the invention.

According to the present invention, the organic light emitting compound for a phosphorescent host represented by [Chemical Formula A] to [Chemical Formula B] has characteristics of long life and low voltage driving compared to conventional materials, and has excellent luminous efficiency, so it is a stable and excellent device It can be used in the manufacture of.

1 is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention.
2 is a graph showing life evaluation of devices of Comparative Examples 2, 1 and 8 of the present invention.

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

The present invention is an organic light emitting compound that can be used in the light emitting layer of an organic light emitting device, and the organic light emitting compound represented by the following [Chemical Formula A] to [Chemical Formula B] has a longer life and lower voltage of the organic light emitting device than the organic light emitting material according to the prior art. It was found that a stable and excellent device can be manufactured by being shown to be capable of showing driving characteristics and good luminous efficiency.

More specifically, the present invention provides a compound represented by any one selected from the following [Formula A] to [Formula B].

[Formula A]

[Formula B]

In the [Formula A] or [Formula B],

The A ₁ to A ₄ and R ₁ to R ₁₆ are each the same or different, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms , A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon number of 5 to 30 Cycloalkenyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted An arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted arylamine group having O, N or S as a hetero atom It is any one selected from a C2-C50 heteroaryl group, a cyano group, a nitro group, and a halogen group, and the A ₁ to A ₄ and R ₁ to R ₈ are each connected with a substituent adjacent to each other to be an alicyclic, aromatic Can form a monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, and O ;

The L ₁ and L ₂ is a linking group, a single bond, a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted C 2 to C 60 Alkenylene group, substituted or unsubstituted alkynylene group having 2 to 60 carbon atoms, substituted or unsubstituted C3 to C60 A cycloalkylene group, 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;

X is a linking group, or a single bond or -C(R ₃₁ R ₃₂ )-, NR ₃₃ , O, S, SiR ₃₄ R ₃₅ , GeR ₃₆ R ₃₇ , PR ₃₈ , PR ₃₉ (=O), C=O, BR ₄₀ Is,

R ₃₁ to R ₄₀ are the same as defined in R ₁ to R ₁₆ ;

The m, n, n'and p are each independently an integer of 1 to 3,

When m, n, n'and p are each 2 or more, each linking group and indole group are the same or different from each other;

In Formula A, p of R ₅ to R ₈ and R ₁₀ to R _{13 ,} R ₁₅ and R ₁₆ One of each is a single bond connected to the L ₂ ,

In Formula B, p of R ₅ to R ₈ is a single bond connected to L ₂ ;

'Substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms , C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, C2-C24 heteroarylalkyl group , C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 hetero arylamino group, C1-C24 alkylsilyl group, C1-C24 arylsilyl It means substituted with one or more substituents selected from the group consisting of a group and an aryloxy group having 1 to 24 carbon atoms.

In addition, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" and "substituted or unsubstituted aryl group having 5 to 50 carbon atoms", the carbon number is 1 to 30 The range of the number of carbon atoms of the alkyl group and the aryl group having 5 to 50 carbon atoms of each means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when the substituent is considered to be unsubstituted 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 4 carbon atoms.

On the other hand, the aryl group used in the compound of the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members, In addition, when the aryl group has a substituent, it may be fused with neighboring substituents to further form a ring.

Specific examples of the aryl include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluorane. Including tenil, etc., but is not limited thereto.

At least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R''), R'and R" are each independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), an amidino group, 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 alkenyl 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, It may be substituted with a C2-C24 heteroaryl group or a C2-C24 heteroarylalkyl group.

The heteroaryl group, which is a substituent used in the compound of the present invention, is a heteroaromatic organic radical having 2 to 24 carbon atoms which may contain 1 to 4 heteroatoms selected from N, O, P or S in each ring in the aryl group. It means, and the rings may be fused to form a ring. And at least one hydrogen atom in the heteroaryl group may be substituted with the same substituent as in the case of 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, and at least one hydrogen atom in the alkyl group is The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group that is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, 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 as a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclo Butylsilyl, dimethylfurylsilyl, and the like. At least one hydrogen atom in the silyl group may be substituted with the same substituent as in the case of the aryl group.

[Chemical Formula A] may be one compound selected from the following [Chemical Formula 101] to [Chemical Formula 103] depending on the case where p is 1 to 3.

[Formula 101]

[Formula 102]

[Chemical Formula 103]

Substituents A ₁ to A ₄ and R ₁ to R ₁₆ , X, in the [Formula 101] to [Formula 103] L ₁ , L ₂ , m, n, n'and p are each the same as defined above, and when the indole group to be substituted is 2 or more, each indole group may be the same or different from each other.

In addition, the [Chemical Formula B] is divided into a compound according to the same structural formula as [Chemical Formula 101] to [Chemical Formula 103] except that the nitrogen portion of the indole is bonded to the linking group L2 depending on the case where p is 1 to 3 I can lose. ,

In the [Formula A] and [Formula B] of the present invention, the linking groups L ₁ and L ₂ are the same or different, and each independently, may be a single bond, or may be any one selected from Structural Formulas 1 to 8 below.

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

[Structural Formula 5] [Structural Formula 6] [Structural Formula 7] [Structural Formula 8]

Here, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring in the substituents L ₁ and L ₂ .

In addition, in the present invention, the substituents A ₁ to A ₄ and R ₁ to R ₁₆ of [Chemical Formula A] and [Chemical Formula B] are the same or different, respectively, and independently of each other, hydrogen and deuterium; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 5 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; may be one selected from, and m, n, n'and p may be 1 or 2.

In addition, in the present invention, the compound of [Chemical Formula A] and [Chemical Formula B] may be one selected from the following [Chemical Formula 1] to [Chemical Formula 10] according to the change of X, but is not limited thereto.

[Formula 1] [Formula 2]

[Formula 3] [Formula 4]

[Formula 5] [Formula 6]

[Formula 7] [Formula 8]

[Formula 9] [Formula 10]

In the [Formula 1] to [Formula 10], substituents A ₁ to A ₄ and R ₁ to R ₁₆ , R ₃₃ to R ₃₈ , L ₁ , L ₂ , n, n'and p are each the same as defined above, but one of R ₁₀ to R ₁₆ is a single bond bonded to the linking group L ₂ .

In the present invention, the substituents R ₁ to R ₈ Each may be a compound that does not form a ring by being linked with a substituent adjacent to each other. That is, in the present invention, the compound represented by any one selected from [Chemical Formula A] and [Chemical Formula B] is composed of only three rings without additional ring formation in the linking group located between the linking groups L ₁ and L ₂ It means that it is a compound.

In addition, in the present invention, the [Chemical Formula A] and [Chemical Formula B] are represented by the following [Formula 11] to [Formula 22] by fusion of each of the substituents R ₁ to R ₄ to each other to form a monocyclic or polycyclic ring It may be represented by the compound to be displayed, but is not limited thereto.

[Formula 11] [Formula 12]

[Formula 13] [Formula 14]

[Formula 15] [Formula 16]

[Formula 17] [Formula 18]

[Formula 19] [Formula 20]

[Formula 21] [Formula 22]

Substituents A ₁ to A ₄ and R ₁ to R ₁₆ , X, in the [Formula 1] to [Formula 22] L ₁ , L ₂ , m, n, n'and p are each the same as defined above, but one of the R ₁₀ to R ₁₆ is a single bond bonded to the linking group L _2, and Ra and Rb are the R ₁ to Same as defined in R _{16 ,} j is an integer from 1 to 6, and when j is 2 or more, each Ra can be the same or different and each Rb can be the same or different.

In addition, in the present invention, the substituent R ₉ of [Chemical Formula A] and [Chemical Formula B] may be a functional group including deuterium or deuterium, and the substituents A ₁ to A ₄ may include deuterium. That is, the substituent R ₉ and the substituents A ₁ to A ₄ may be functional groups such as deuterium, an alkyl group substituted with deuterium, an aryl group substituted with deuterium, and a heteroaryl group substituted with deuterium.

In addition, in the present invention, the substituents A ₁ to A ₄ of [Chemical Formula A] and [Chemical Formula B] may be hydrogen or deuterium, respectively.

The deuterium-substituted compound exhibits a lower zero point energy and lower vibration energy level as the atomic mass of deuterium is twice that of hydrogen compared to the compound bound to hydrogen. In addition, the physicochemical properties, such as the length of chemical bonds related to deuterium, appear different from those of hydrogen, and in particular, the elongation amplitude of the CD bond is smaller than that of the CH bond, so the Van der Waals radius of deuterium is smaller than that of hydrogen, and in general, CD It indicates that the bond is shorter and stronger than the CH bond.

In addition, when substituted with deuterium, the energy in the ground state is lowered, and as the bond length of deuterium and carbon is shortened, the molecular hardcore volume decreases, and accordingly, the electrical polarizability can be reduced. It is known that the volume of the thin film can be increased by weakening the intermolecular interaction. Such a characteristic may be effective in lowering the crystallinity of the thin film, that is, an amorphous state, and in general, it may be effective to increase the life and driving characteristics of the organic light emitting device, and the heat resistance may be further improved.

또는

이고, n, n'및 p 는 각각 1일 수 있다. In addition, in the present invention, the linking groups L ₁ and L ₂ are the same or different, and each independently, is a single bond,

or

And n, n'and p may each be 1.

In addition, in the present invention, the compound represented by [Chemical Formula A] or [Chemical Formula B] may be any one of the following [Compound 1] to [Compound 130].

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20] [Compound 21]

[Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41] [Compound 42]

[Compound 43] [Compound 44] [Compound 45]

[Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51]

[Compound 52] [Compound 53] [Compound 54]

[Compound 55] [Compound 56] [Compound 57]

[Compound 58] [Compound 59] [Compound 60]

[Compound 61] [Compound 62] [Compound 63]

[Compound 64] [Compound 65] [Compound 66]

[Compound 67] [Compound 68] [Compound 69]

[Compound 70] [Compound 71] [Compound 72]

[Compound 73] [Compound 74] [Compound 75]

[Compound 76] [Compound 77] [Compound 78]

[Compound 79] [Compound 80] [Compound 81]

[Compound 82] [Compound 83] [Compound 84]

[Compound 85] [Compound 86] [Compound 87]

[Compound 88] [Compound 89] [Compound 90]

[Compound 91] [Compound 92] [Compound 93]

[Compound 94] [Compound 95] [Compound 96]

[Compound 97] [Compound 98] [Compound 99]

[Compound 100] [Compound 101] [Compound 102]

[Compound 103] [Compound 104] [Compound 105]

[Compound 106] [Compound 107] [Compound 108]

[Compound 109] [Compound 110] [Compound 111]

[Compound 112] [Compound 113] [Compound 114]

[Compound 115] [Compound 116] [Compound 117]

[Compound 118] [Compound 119] [Compound 120]

[Compound 121] [Compound 122] [Compound 123]

[Compound 124] [Compound 125] [Compound 126]

[Compound 127] [Compound 128] [Compound 129]

[Compound 130]

In addition, the present invention is 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 may include one or more of the organic light emitting compounds in the present invention in the present invention.

In the present invention, "(organic layer) contains one or more organometallic compounds" means "(organic layer) one organometallic compound belonging to the scope of the present invention or two different kinds belonging to the organometallic compound It can be interpreted as "may include the above compounds.

In addition, the organic layer containing the organic light-emitting compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. have. In this case, the organic layer interposed between the first electrode and the second electrode may include an emission layer, the emission layer is formed of a host and a dopant, and the organic emission compound of the present invention may be used as a host.

Meanwhile, in the present invention, a dopant material may be used in addition to a host for the emission layer. When the emission layer includes a host and a dopant, the content of the dopant may be generally selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

Meanwhile, in the present invention, a known electron transport material may be used as the material for the electron transport layer to stably transport electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinorate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin-10-). olate: Bebq2), ADN, compound 201, compound 202, oxadiazole derivatives such as PBD, BMD, BND, etc. may be used, but the present invention is not limited thereto.

TAZ BAlq

Compound 201 Compound 202 BCP

In addition, as for the electron transport layer used in the present invention, an organometallic compound represented by Formula C may be used alone or in combination with the electron transport layer material.

[Formula C]

In [Chemical Formula C],

Y is a portion in which any one selected from C, N, O, and S is directly bonded to the M to form a single bond, and a portion in which any one selected from C, N, O, and S forms a coordination bond to the M. And is a ligand chelated by the single bond and the coordination bond

The M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom, and the OA is a monovalent ligand capable of a single bond or coordination bond with the M,

O is oxygen,

A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted C2 to C20 An alkynyl group, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, and a substituted or unsubstituted hetero atom having O, N or S as a hetero atom and having 2 to 50 carbon atoms Is any one selected from aryl groups,

When M is one metal selected from alkali metals, m = 1, n = 0,

When M is one metal selected from alkaline earth metals, m=1, n=1, or m=2, n=0,

When M is boron or aluminum, m is any one of 1 to 3, and n is any one of 0 to 2, which satisfies m + n = 3;

'Substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It means substituted with one or more substituents selected from the group consisting of aryloxy group, aryl group, heteroaryl group, germanium, phosphorus and boron.

In the present invention, Y is the same or different, and may be any one independently selected from the following [Structural Formula C1] to [Structure C39], but is not limited thereto.

[Structural Formula C1] [Structural Formula C2] [Structural Formula C3]

[Structural Formula C4] [Structural Formula C5] [Structural Formula C6]

[Structural Formula C7] [Structural Formula C8] [Structural Formula C9] [Structural Formula C10]

[Structural Formula C11] [Structural Formula C12] [Structural Formula C13]

[Structural Formula C14] [Structural Formula C15] [Structural Formula C16]

[Structural Formula C17] [Structural Formula C18] [Structural Formula C19] [Structural Formula C20]

[Structural Formula C21] [Structural Formula C22] [Structural Formula C23]

[Structural Formula C24] [Structural Formula C25] [Structural Formula C26]

[Structural Formula C27] [Structural Formula C28] [Structural Formula C29] [Structural Formula C30]

[Structural Formula C31] [Structural Formula C32] [Structural Formula C33]

[Structural Formula C34] [Structural Formula C35] [Structural Formula C36]

[Structural Formula C37] [Structural Formula C38] [Structural Formula C39]

In the [Structural Formula C1] to [Structural Formula C39],

R is the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted A heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or Unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylamino group, and substituted or unsubstituted C6-C30 arylsilyl It is selected from groups, and may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or a fused ring.

Hereinafter, the organic light-emitting device of the present invention will be described with reference to FIG. 1.

1 is a cross-sectional view showing the 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 if necessary, a hole injection layer 30 and an electron The injection layer 70 may be further included, and in addition, one or two intermediate layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, an organic light-emitting device of the present invention and a method of manufacturing the same are as follows. First, an anode 20 is formed by coating a material for an anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a typical organic EL device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness is preferable. In addition, as a material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum thermal evaporation or spin coating on the anode 20 electrode. Then, the hole transport layer material is vacuum thermally evaporated or spin coated on the hole injection layer 30 to form the hole transport layer 40.

The hole injection layer material is not particularly limited as long as it is commonly used in the art, and may be used, for example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ], etc. However, the present invention is not necessarily limited thereto.

In addition, the material of the hole transport layer is not particularly limited as long as it is commonly used in the art, and for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1 -Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (a-NPD) and the like can be used. However, the present invention is not necessarily limited thereto.

Subsequently, an organic light-emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light-emitting layer 50 by vacuum deposition or spin coating to form a thin film. can do. 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 because when holes pass through the organic light emitting layer and flow into the cathode, the life and efficiency of the device are reduced. . In this case, the hole blocking material to be used is not particularly limited, but must have an electron transport ability and an ionization potential higher than that of the light emitting compound, and representatively, BAlq, BCP, TPBI, etc. may be used.

As the material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, and Chemical Formulas 101 to 107 may be used, but is not limited thereto. .

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

Formula 101 Formula 102 Formula 103

화학식 104 화학식 105 화학식 106

Formula 104 Formula 105 Formula 106

Chemical Formula 107

After depositing the electron transport layer 60 on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode-forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form the cathode 80 electrode. Here, the cathode-forming metal is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-ridium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) or the like may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

In addition, the emission layer may be formed of a host and a dopant.

In addition, according to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 Å.

In this case, the dopant used in the light emitting layer may be one or more compounds selected from compounds represented by the following general formulas (A-1) to (J-1).

[General Formula A-1]

The M is selected from the group consisting of metals of groups 7, 8, 9, 10, 11, 13, 14, 15, and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. In addition, the L ₁ , L ₂ and L ₃ may be the same as or different from each other as a ligand, and may each independently include any one selected from the following structural formula D, but is not limited thereto.

Further, "*" in the following structural formula D represents a site coordinated with the metal ion M.

[Structural Formula D]

In the structural formula D, R is different from or identical to each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted Or an unsubstituted C5-C50 heteroaryl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alke Nyl group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted C 6 to C atoms It may be any one selected from 30 arylsilyl groups;

Each of R is independently selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen May be further substituted with one or more substituents;

In addition, R may be connected to each of the adjacent substituents by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

The L may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or a fused ring.

As an example, the dopant represented by [General Formula A-1] may be any one selected from the following compounds.

[General Formula B-1]

In the general formula B-1,

M ^A1 represents the same metal ion as defined in the general formula (A-1), and Y ^A11 and Y ^A14 ,Y ^A15 and Y ^A18 Each independently represents a carbon atom or a nitrogen atom, Y ^A12 , Y ^A13 ,Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, and L ^A11 ,L ^A12 ,L ^A13 ,L ^A14 represents a linking group as defined above, respectively, and Q ^A11 and Q ^A12 represent a partial structure containing an atom bonded to M ^A1 .

An exemplary structure of the compound represented by the general formula B-1 is as follows, but is not limited thereto.

[General Formula C-1]

In the general formula C-1,

M ^B1 represents the same metal ion as defined in the general formula A-1, Y ^B11 , Y ^B14 ,Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, and Y ^B12 , Y ^B13 , Y ^B16 and Y ^B17 are each independently a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, and oxygen Represents an atom or a sulfur atom, and L ^B11 ,L ^B12 ,L ^B13 ,L ^B14 represents a linking group, and Q ^B11 ,Q ^B12 represents a partial structure containing an atom bonded to M ^B1 .

An exemplary structure of the compound represented by the general formula C-1 is as follows, but is not limited thereto.

[General Formula D-1]

In the general formula D-1,

M ^C1 represents the same metal ion as the metal ion defined in the general formula A-1,

R ^C11 and R ^C12 each independently represent a hydrogen atom, a substituent that is connected to each other to form a 5-membered ring, and a substituent that is not connected to each other,

R ^C13 and R ^C14 each independently represent a hydrogen atom, a substituent that is connected to each other to form a 5-membered ring, a substituent that is not connected to each other, and G ^C11 ,G ^C12 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonded to M ^C1 .

An exemplary structure of the compound represented by the general formula D-1 is as follows, but is not limited thereto.

[General Formula E-1]

In the general formula E-1,

M ^D1 represents the same metal ion as defined in the general formula (A-1), G ^D11 , G ^D12 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, J ^D11 , J ^D12 , J ^D13 and Each of J ^D14 independently represents an atomic group necessary to form a 5-membered ring, and L ^D11 and L ^D12 represent a linking group.

An exemplary structure of the compound represented by the general formula E-1 is as follows, but is not limited thereto.

[General Formula F-1]

In the general formula F-1,

M ^E1 represents the same metal ion as defined in General Formula A-1, J ^E11 and J ^E12 each independently represent a group of atoms required to form a five-membered ring, and G ^E11 , G ^E12 , G ^E13 and G ^E14 are Each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 ,Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

An exemplary structure of the compound represented by the general formula F-1 is as follows, but is not limited thereto.

[General Formula G-1]

In the general formula G-1,

M ^F1 represents the same metal ion as defined in General Formula A-1,

L ^F11 ,L ^F12 and L ^F13 represent a linking group, R ^F11 ,R ^F12 ,R ^F13 and R ^F14 represent a substituent, and R ^F11 and R ^F12 ,R ^F12 And R ^F13 , R ^F13 and R ^F14 may be linked to each other to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. Further, Q ^F11 and Q ^F12 represent a partial structure containing an atom bonded to M ^F1 .

An exemplary structure of the compound represented by the general formula G-1 is as follows, but is not limited thereto.

[General Formula H-1] [General Formula H-2] [General Formula H-3]

In the general formula H-1,

R ¹¹ , R ¹² are substituents of alkyl, aryl or heteroaryl; In addition, a fused ring may be formed with a substituent adjacent to each other, and q11 and q12 are integers of 0 to 4, preferably 0 to 2.

In addition, when q11 and q12 are 2 to 4, a plurality of R11 and R12 are the same or different, respectively,

L ¹ is a ligand that binds to platinum, and is preferably a ligand capable of forming an ortho metalized platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, a halogen ligand, and more preferably an ortho metal. ) A ligand that forms a platinum complex, a bipyridyl ligand, or a phenanthroline ligand.

n ¹ is an integer of 0 to 3, preferably 0, and m ¹ is 1 or 2, preferably 2.

In addition, it is preferable that n ¹ and m ¹ make the metal complex represented by the general formula H-1 become a neutral complex.

In the general formula H-2, R ²¹ , R ²² , n ² , m ² , q ²² , L ² are the same as the R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² , L ¹ , respectively, and q ²¹ is an integer of 0-2, and 0 is preferable.

In the general formula H-3, R ³¹ , n ³ , m ³ , L ³ are the same as R ¹¹ , n ¹ , m ¹ , L ¹ , respectively, and q ³¹ represents an integer of 0 to 8, and 0 to 2 is preferable and 0 is more preferable.

Examples of specific compounds of the general formulas H-1 to H-3 are as follows, but are not limited thereto.

[General Formula I-1]

In the general formula I-1,

Ring A, Ring B, Ring C, and Ring D represent a nitrogen-containing heterocycle in which any two of the rings A to D may have a substituent, and the other two rings are an aryl ring or heteroaryl which may have a substituent. Represents and represents a ring, and a condensed ring can be formed by ring A and ring B, ring A and ring C, and/or ring B and ring D. X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which two of them are coordinated to a platinum atom, and the other two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (term) or a bond, but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. Z ¹ , Z ² , Z ³ and Z ⁴ are any two representing a coordination bond, and the other two represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of specific compounds of the general formula I-1 are as follows, but are not limited thereto.

[General Formula J-1]

In the general formula J-1,

M represents the same metal ion as defined in General Formula A-1, Ar1 represents a substituted or unsubstituted cyclic structure, and in the two azomethine bonds (-C=N-) bonded to the M , The nitrogen atom (N) is each bonded to the M, and as a whole, forms a tridentate ligand bonded to the M at three loci.

In addition, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same as or different from each other, and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a monodentate ligand.

In the general formula J-1, it is preferable that M is Pt. In addition, it is preferable that Ar1 is selected from a 5-membered ring, a 6-membered ring, and a condensed ring group thereof.

Examples of specific compounds of the general formula J-1 are as follows, but are not limited thereto.

In addition, the emission layer may further include various hosts and various dopant materials in addition to the dopant and host.

In addition, in the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process. Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state, and the solution process is used to form each layer. It refers to a method of forming a thin film through a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc. by mixing a material used as a material for use with a solvent.

In addition, the organic light emitting device in the present invention includes a flat panel display device; Flexible display device; Monochrome or white flat lighting devices; And a single color or white flexible lighting device; may be used in any one device selected from.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereto.

(Example)

Synthesis Example 1. Synthesis of [Compound 1]

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

[Reaction Scheme 1-1]

[Intermediate 1-a]

6-bromoindole 50.0 g (255.0 mmol), iodobenzene 10.4 g (510.0 mmol), copper powder 32.4 g (510.0 mmol), 18-crown-6 13.5 g (51.0 mmol), potassium carbonate 105.7 g (765.0 mmol) ) In order, 500 ml of 1,2-dichlorobenzene was added, and then refluxed and stirred at 180° C. for 1 day.

When the reaction was completed, the solution was concentrated under reduced pressure after high-temperature filtering, and the organic layer solution was subjected to column chromatography with hexane to obtain 57.6 g of [Intermediate 1-a]. (83% yield)

Synthesis Example 1-2) Synthesis of [Intermediate 1-b]

[Scheme 1-2]

[Intermediate 1-a] [Intermediate 1-b]

After dissolving 57.6 g (211.6 mmol) of the [Intermediate 1-a] compound obtained from [Scheme 1-1] in 600 ml of tetrahydrofuran under a stream of nitrogen, and stirring at -78 °C, 159 ml of 1.6M normal-butyllithium (253.9 mmol) was slowly added dropwise, and when the dropwise addition was completed, the mixture was stirred for 1 hour while maintaining -78°C. After that, 26.4 g (253.9 mmol) of trimethylborate was slowly added dropwise, and then raised to room temperature and stirred for 2 hours.

Upon completion of the reaction, 300 ml of a 2M aqueous hydrochloric acid solution was added dropwise at room temperature, followed by stirring for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, and the organic layer was concentrated under reduced pressure and recrystallized with dichloromethane and hexane to obtain 28.6 g of [Intermediate 1-b]. (Yield 57%)

Synthesis Example 1-3) Synthesis of [Intermediate 1-c]

[Scheme 1-3]

[Intermediate 1-c]

Carbazole 150.0 g (762.6 mmol) was dissolved in 1.0 L of dimethylformamide, and then stirred at 0°C. Thereafter, 135.7 g (762.6 mmol) of N-bromomucinimide was dissolved in 0.5 L of dimethylformamide, and then slowly added dropwise for 1 hour while maintaining 0°C. When the dropwise addition is complete, the mixture is raised to room temperature and stirred for 12 hours.

When the reaction was completed, distilled water was added dropwise at room temperature, and when brown crystals were formed, the crystals were filtered and recrystallized with toluene and methanol to obtain 110.0 g of [Intermediate 1-c]. (Yield 58%)

Synthesis Example 1-4) Synthesis of [Intermediate 1-d]

[Scheme 1-4]

[중간체 1-d]

[Intermediate 1-d]

At room temperature, 2-aminobenzonitrile (20.0 g, 169 mmol) and 140 mL of tetrahydrofuran were added to a round bottom flask under a nitrogen stream, followed by stirring. 112.9 mL (339 mmol) of phenyl magnesium bromide (3.0 M in Et ₂ O) was added dropwise. After reflux stirring for about 1 hour, the temperature was set to 0°C. Ethyl chloroformate (22.0g, 203mmol) was added dropwise and stirred under reflux for about 1 hour. An aqueous ammonium chloride solution was added until it became slightly acidic, and the resulting solid was filtered and washed with water and heptane to obtain 30.1 g of [Intermediate 1-d]. (Yield 80%)

Synthesis Example 1-5) Synthesis of [Intermediate 1-e]

[Scheme 1-5]

[Intermediate 1-e]

At room temperature, the synthesized [intermediate 1-d] (30.0 g, 135 mmol) and about 80 mL of phosphorus oxychloride were added to a round bottom flask under a nitrogen stream, followed by stirring. After reflux stirring overnight, the temperature was cooled to -20℃ the next day, and water was slowly added dropwise about 400mL. The resulting solid was filtered and washed with water, methanol, and heptane. Recrystallization from toluene and heptane gave 14.6 g of [Intermediate 1-e] as a white solid. (Yield 44.9%)

Synthesis Example 1-6) Synthesis of [Intermediate 1-f]

[Scheme 1-6]

[Intermediate 1-f]

At room temperature, 2.1 g (53 mmol) of 60% sodium hydride and 50 mL of dimethylformamide were added to a round bottom flask under a flow of nitrogen, and the mixture was stirred for about 30 minutes. 10.0 g (41 mmol) of [Intermediate 1-c] obtained from [Scheme 1-3] and 100 mL of dimethylformamide were added dropwise, followed by stirring for about 1 hour. 12.7g (53 mmol) of the synthesized [Intermediate 1-e] and 100 mL of dimethylformamide were added, followed by stirring overnight. A solid formed by adding 600 mL of distilled water to the flask was filtered. Recrystallized from toluene to obtain 14.3 g of [Intermediate 1-f]. (Yield 78.1%)

Synthesis Example 1-7) Synthesis of [Compound 1]

[Scheme 1-7]

[Compound 1]

The synthesized [intermediate 1-f] 14.3 g (32 mmol), the synthesized [intermediate 1-b] 9.0 g (38 mmol), tetrakis (triphenylphosphine) palladium 0.7 g (0.64 mmol), potassium carbonate 8.8 g (64 mmol), 1,4-dioxane 80 ml, toluene 80 ml, and distilled water 30 ml were added and stirred under reflux overnight. When the reaction is completed, extraction is performed using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from dichloromethane and acetone to obtain 4.4 g of [Compound 1]. (Yield 24.6%)

MS (MALDI-TOF): m/z 563 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103,104.8,109.5,109.9,111.6,116.8,118.9,119.3,119.4,119.8,121.3,121.4,125.5,126.6,127.4,127.5,127.7,128.3,128.5,128.7,129.2,129.3,131.8,132.3,133,133.1,138.7, 141.6,143.7,144.4,145.9,149.3,155.8,161 [40C]

Synthesis Example 2. Synthesis of Compound 2

It was prepared in the same manner as in Synthesis Examples 1-1 to 1-2 by using 4-bromoindole instead of 6-bromoindole used in [Scheme 1-1], and [ Using 2-bromocarbazole instead of the intermediate 1-c], 4.2 g of [Compound 2] was synthesized using the same method as in Synthesis Examples 1-6 to 1-7. (Yield 27%)

MS (MALDI-TOF): m/z 562 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

104.8,107.6,108.4,109.5,109.9,118.9,119.3,119.8,121.3,121.4,125.5,125.6,125.7,126.6,127.4,127.5,127.7,128.5,128.6,128.7,129.2,129.3,129.8,131.8,132.3, 133,133.1,138.7,141.6,144.4,145.9,149.3,155.8,161 [40C]

Synthesis Example 3. Synthesis of Compound 3

Synthesis Example 3-1) Synthesis of [Intermediate 3-a]

[Reaction Scheme 3-1]

[Intermediate 3-a]

In a round bottom flask, methyl aminobenzoate (50.0g, 330mmol), iodobenzene (56.3g, 276mmol), palladium acetate (1.2g, 5.6mmol), xantfos (6.4g, 11.02mmol), cesium carbonate (126g, 386mmol), toluene (1000 mL) was added and stirred under reflux for 24 hours. After the reaction was completed the next day, the reaction was cooled to room temperature, filtered, and toluene was concentrated under reduced pressure to remove the solvent, and the concentrate was subjected to column chromatography using ethyl acetate and hexane as developing solvents. As a result, 57g (yield 91.2%) of [Intermediate 3-a] Got it.

Synthesis Example 3-2) Synthesis of [Intermediate 3-b]

[Reaction Scheme 3-2]

[Intermediate 3-b]

[Intermediate 3-a] (57g, 250mmol) obtained from [Scheme 3-1] and 800 mL of isopropyl ether were added to a round bottom flask, cooled to 10°C, and then methyl magnesium bromide (1.0M in diethyl ether 875 mL, 875 mmol) ) Was added dropwise for 1 hour, followed by reflux stirring for 2 hours. After cooling to room temperature, 400 mL of a 10% ammonium chloride aqueous solution was added and stirred for 2 hours. The layers were separated to obtain an organic layer and concentrated under reduced pressure to give 30 g (yield 53%) of [Intermediate 3-b].

Synthesis Example 3-3) Synthesis of [Intermediate 3-c]

[Reaction Scheme 3-3]

[Intermediate 3-c]

[Intermediate 3-b] (30g, 130mol) obtained from [Scheme 3-2] was dissolved in 60 mL of phosphoric acid in a round bottom flask and reacted for 6 hours. After completion of the reaction, the reaction solution was obtained in an excess of water to obtain 30 g of [Intermediate 3-c] (yield 53%).

Synthesis Example 3-4) Synthesis of [Intermediate 3-d]

[Scheme 3-4]

[Intermediate 3-d]

[Intermediate 3-c] (20g, 96mmol) obtained from [Scheme 3-3] and 100g of silica gel were dissolved in 200mL of dichloromethane in a round-bottom flask, cooled to 0℃, and then N-bromosaxinimide (17.1g, 96mmol) ) Dissolved in 200 mL of dichloromethane was added dropwise, followed by stirring at room temperature for 5 hours. After completion of the reaction, the mixture was washed 3 times with 600 mL of water, and the solvent was removed to obtain 9.7 g (yield 35.1%) of [Intermediate 3-d].

Synthesis Example 3-5) Synthesis of [Compound 3]

[Scheme 3-5]

[Compound 3]

Instead of [Intermediate 1-c] used in [Scheme 1-6], the synthesized [Intermediate 3-d] was used instead of [Intermediate 1-f] used in Synthesis Example 1-7). 3.9 g (yield 35%) of [Compound 3] was synthesized using the same method as in Synthesis Examples 1-6 to 1-7.

MS (MALDI-TOF): m/z 605 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

22.6,30.9,104.8,109.9,111.7,112.2,118.5,118.7,118.9,119.3,120.1,121.3,122.9,125,125.4,125.5,125.8,126.3,127.5,128.3,128.7,129,129.2,129.3,130.5,130.9,131.4, 131.7,131.8,136,137.1,138.7,141.6,145.9,149.2,155.6,160 [43C]

Synthesis Example 4. Synthesis of [Compound 4]

[Reaction Scheme 4-1]

[Compound 4]

Using 3-bromo-10H-phenothiazine instead of [intermediate 1-c] used in the above [Scheme 1-6] was used instead of [Intermediate 1-f] used in Synthesis Example 1-7) Using the same method as in Synthesis Examples 1-6 to 1-7, 3.4 g (yield 33%) of [Compound 4] was obtained.

MS (MALDI-TOF): m/z 595 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

104.8,109.9,112.7,118.2,118.5,118.7,118.9,119.3,120.2,121.3,122.2,122.9,125,125.5,125.8,126.6,127.2,127.3,127.5,128.1,128.3,128.7,129.2,129.3,130.8,131.4, 131.8,138.7,141.6,144.3,145.4,145.9,149.2,155.6,160 [40C]

Synthesis Example 5. Synthesis of [Compound 5]

Synthesis Example 5-1. Synthesis of [Intermediate 5-a]

[Scheme 5-1]

[Intermediate 5-a]

13.5 g (yield 72.8%) of [Intermediate 5-a] was obtained using the same method, except that 2,3-dimethylindole was used instead of [Intermediate 3-c] used in [Scheme 3-4].

Synthesis Example 5-2. Synthesis of [Compound 5]

Synthesis Example 1-1) to Synthesis Example 1-7), except that [intermediate 5-a] synthesized in [Scheme 5-1] was used instead of 6-bromoindole used in [Scheme 1-1] 5.1g (yield 28%) of [Compound 5] was obtained using the same method as described above.

MS (MALDI-TOF): m/z 591 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

9.5,10.7,103,109.5,109.9,110111.6,116.8,118.9,119.3,119.4,119.8,121.3,121.4,125.5,126.6,127.4,127.5,127.7,128.5,128.6,128.7,129.2,129.3,131.8,132.3,133,133.1, 136.3,141.6,143.7,144.4,146.6,149.3,151,155.8,161 [42C]

Synthesis Example 6. Synthesis of [Compound 6]

Synthesis Example 6-1. Synthesis of [Intermediate 6-a]

[Scheme 6-1]

[Intermediate 6-a]

In a round-bottom flask, 4-bromophenylhydrazine hydrochloride (110g, 492mmol), benzylphenylketone (64g, 328mmol), and 550mL of ethanol were all added and refluxed for 12 hours. After neutralization with a base, it was extracted with water and ethyl acetate. The organic material was concentrated under reduced pressure and recrystallized from hexane. After the filter was dried, 68.3 g of [Intermediate 6-a] (yield 39.8%) was obtained.

Synthesis Example 6-2. Synthesis of [Intermediate 6-b]

[Scheme 6-2]

[Intermediate 6-b]

[Intermediate 6-a] (25g, 72mmol) synthesized in [Scheme 6-1], iodobenzene 58.6g, 287mmol), copper (13.7g, 215mmol), potassium carbonate (49.6g, 359mmol) in a round bottom flask , 18-crown-6 (3.8g, 14mmol) and 125mL of 1,2-dichlorobenzene were added and refluxed for 72 hours. After the reaction was completed, cooled to room temperature, an excess of methanol was added to generate a solid, filtered, and column chromatography was performed using ethyl acetate and hexane as developing solvents. As a result of [Intermediate 6-b] 11.3g (yield 37%) Got it.

Synthesis Example 6-3. Synthesis of [Compound 6]

Synthesis Example 1-2) to Synthesis Example 1-7, except that [Intermediate 6-b] synthesized in [Scheme 6-2] was used instead of [Intermediate 1-a] used in [Scheme 1-2] ) Using the same method as [Compound 6] to obtain 4.2g (26% yield).

MS (MALDI-TOF): m/z 715 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103,109.5,109.7,111.6,116.8,118.9,119.3,119.4,119.8,121.4,125.5,126.6,127.4,127.5,127.7,128.5,128.7,129.2,129.3,131.8,132.3,133,133.1,134.7,136.1,136.8,141.6, 143.7,144.4,146.7,149.3,155.8,161 [52C]

Synthesis Example 7. Synthesis of [Compound 7]

Synthesis Example 7-1. Synthesis of [Intermediate 7-a]

[Scheme 7-1]

[Intermediate 7-a]

At room temperature, in a round-bottom flask under a stream of nitrogen, indole (16.8 g, 143 mmol), 1-bromo-4-iodobenzene 48.7 g (172 mmol), tris(dibenzylidineacetone) dipalladium (0) 2.6 g (2.87 mmol), tri-tertiary-butylphosphonium tetrafluoroborate 4.2 g (14.3 mmol), sodium tertiary butoxide 27.6 g (287 mmol), and xylene (300 mL) were added and stirred under reflux for 24 hours. Made it. After the reaction solution was filtered using Celite, the filtrate was concentrated under reduced pressure, and then purified by silica gel column chromatography to obtain [Intermediate 7-a] (29.1 g, 107 mmol). (Yield 74.9%)

Synthesis Example 7-2. Synthesis of [Intermediate 7-b]

[Reaction Scheme 7-2]

[Intermediate 7-b]

At room temperature, 3-bromocarbazole (20.0 g, 81.3 mmol), bis (pinacolato) diboron (22.7 g, 89.4 mmol), potassium acetate (17.5 g, 179 mmol), PdCl in a round bottom flask under a nitrogen stream. ₂ (dppf) [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.8 g, 2.44 mmol) and toluene (200 mL) were added, followed by reflux stirring for 12 hours. After filtering the reaction solution using Celite, the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography to obtain [Intermediate 7-b] (16.7 g, 57.0 mmol). (Yield 70.1%)

Synthesis Example 7-3. Synthesis of [Intermediate 7-c]

[Scheme 7-3]

[Intermediate 7-a] [Intermediate 7-b] [Intermediate 7-c]

At room temperature, [Intermediate 7-a] (7.5 g, 27.5 mmol) obtained from [Scheme 7-1] and [Intermediate 7-b] (8.4 g, 30.2 mmol) obtained from [Scheme 7-2] were placed in a round bottom flask at room temperature. , Potassium carbonate (11.4 g, 82.4 mmol), tetrakistriphenylphosphine palladium (1.3 g, 1.10 mmol), tetrahydrofuran (100 mL), and distilled water (20 mL) were added, followed by reflux stirring for 12 hours. After cooling the reaction solution to room temperature, ethyl acetate and distilled water were added to separate the layers. The organic layer was concentrated under reduced pressure and purified by silica gel column chromatography to obtain [Intermediate 7-c] (7.8 g, 21.8 mmol). (Yield 79.2%)

Synthesis Example 7-4. Synthesis of [Compound 7]

[Scheme 7-4]

[Compound 7]

Using the same method as in Synthesis Example 1-6, except that [Intermediate 7-c] synthesized in [Scheme 7-3] was used instead of [Intermediate 1-c] used in [Scheme 1-6] [Compound 7] 3.5 g was obtained. (Yield 34%)

MS (MALDI-TOF): m/z 563 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103,104.8,109.5,111.6,114.1,116.8,119.4,119.8,120.7,121.4,125.5,126.6,127.4,127.5,127.7,128.3,128.5,128.7,129.2,129.4,131.8,132.3,133,133.1,134.7,137.6,143.7, 144.4,149.3,155.8,161 [40C]

Synthesis Example 8. Synthesis of [Compound 8]

Synthesis Example 8-1) Synthesis of [Intermediate 8-a]

[Scheme 8-1]

[Intermediate 8-1-a] [Intermediate 8-a]

In a round bottom flask, bromobenzene-d5 (500 g, 3085 mmol), copper iodide (117.5 g, 615 mmol), trans-4-hydroxy-L-proline (162 g, 1235 mmol), potassium carbonate (1279.5 g, 9255 mmol) and dimethyl 2500 mL of sulfoxide was added and stirred. After installing the gas trap, 2900 mL of aqueous ammonia (28%) was slowly added dropwise. Stir at 80° C. overnight. After the reaction was completed, the mixture was extracted several times with ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and then subjected to column chromatography with ethyl acetate and heptane to obtain 185 g (yield 61.1%) of the liquid [Intermediate 8-1-a], and the synthesized [Intermediate 8-1-a] in a round bottom flask (185g, 1887mmol), trichloroacetonitrile (326.6g, 2257mmol) and 1850mL dichloromethane were added, and tin (IV) chloride (491.2g, 1887mmol) was added. After the flask was installed in an ice-bath, boron trichloride 1M in dichloromethane (243.3 g, 2072 mmol) was slowly added dropwise, followed by reflux stirring for 24 hours. After completion of the reaction, the flask was installed in an ice-bath, and potassium carbonate (3126.5 g, 22616 mmol) dissolved in methanol in a beaker was slowly added dropwise. After dropping all, the mixture was heated to remove dichloromethane, followed by reflux stirring for about 3 hours. After cooling to room temperature, the insoluble solid was filtered, the filtrate was concentrated under reduced pressure, dissolved in ethyl acetate, and washed with an aqueous 2-normal hydrochloric acid solution and water. The organic layer was treated with magnesium sulfate, concentrated under reduced pressure, and then subjected to column chromatography with ethyl acetate and hexane to obtain 41.6 g of [Intermediate 8-a]. (Yield 18.1%)

Synthesis Example 8-2) Synthesis of [Intermediate 8-b]

[Scheme 8-2]

[Intermediate 8-b]

At room temperature, [Intermediate 8-a] (20.0 g, 164 mmol) obtained in [Scheme 8-1] and 140 mL of tetrahydrofuran were added to a round bottom flask under a nitrogen stream, followed by stirring. Phenyl magnesium bromide (3.0 M in Et ₂ O) was added dropwise 109.1 mL (327 mmol). After stirring at reflux for about 1 hour, the temperature was set to 0°C. Ethyl chloroformate (15.5g, 143mmol) was added dropwise and stirred under reflux for about 1 hour. An aqueous ammonium chloride solution was added until it became slightly acidic, and the resulting solid was filtered and washed with water and heptane. 30.2 g of the yellow solid [Intermediate 8-b] was obtained. (Yield 81.5%)

Synthesis Example 8-3) Synthesis of [Intermediate 8-c]

[Scheme 8-3]

[Intermediate 8-c]

At room temperature, [Intermediate 8-b] (30.0 g, 133 mmol) obtained in [Scheme 8-2] and about 80 mL of phosphorus oxychloride were added to a round bottom flask under a nitrogen stream, followed by stirring. After reflux stirring overnight, the temperature was cooled to -20℃ the next day, and water was slowly added dropwise about 400mL. The resulting solid was filtered and washed with water, methanol, and heptane. Recrystallization from toluene and heptane gave 15.2 g of [Intermediate 8-c] as a white solid. (Yield 46.8%)

Synthesis Example 8-4) Synthesis of [Intermediate 8-d]

[Scheme 8-4]

[Intermediate 8-d]

At room temperature, 2.1 g (53 mmol) of 60% sodium hydride and 50 mL of dimethylformamide were added to a round bottom flask under a flow of nitrogen, and the mixture was stirred for about 30 minutes. 10.0 g (41 mmol) of [Intermediate 1-c] obtained from [Scheme 1-3] and 100 mL of dimethylformamide were added dropwise, followed by stirring for about 1 hour. 12.9g (53 mmol) of [Intermediate 8-c] obtained from [Scheme 8-3] and 100 mL of dimethylformamide were added, followed by stirring overnight. A solid formed by adding 600 mL of distilled water to the flask was filtered. Recrystallized from toluene to obtain 14.6 g of [Intermediate 8-d]. (Yield 79.1%)

Synthesis Example 8-5) Synthesis of [Compound 8]

[Scheme 8-5]

[Compound 8]

14.6 g (32 mmol) of the compound represented by [Intermediate 8-d] obtained from [Scheme 8-4], 9.1 g (39 mmol) of the compound represented by [Intermediate 1-b] obtained from [Scheme 1-2] ), tetrakis (triphenylphosphine) palladium 0.7 g (0.64 mmol), potassium carbonate 8.9 g (64 mmol), 1,4-dioxane 80 ml, toluene 80 ml, distilled water 30 ml, and stirred under reflux overnight. When the reaction is completed, extraction is performed using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and recrystallized from dichloromethane and acetone to obtain 4.6 g of [Compound 8] as a pale yellow solid. (Yield 25.3%)

MS (MALDI-TOF): m/z 567 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103,104.8,109.5,109.9,111.6,116.8,118.9,119.3,119.4,119.8,121.3,121.4,125.5,126.6,127,127.5,128,128.3,128.7,129,129.2,129.3,131.8,133,133.1,134,138.7,141.6,143.7,144.4,145.9, 150,155.8,161 [40C]

Synthesis Example 9. Synthesis of Compound 9

Synthesis Example 9-1) Synthesis of [Intermediate 9-a]

[Reaction Scheme 9-1]

[Intermediate 9-a]

Phenylmagnesium bromide (3.0M in Et ₂ O) 110 mL (331 mmol) and tetrahydrofuran 600 mL were added to a round bottom flask under a nitrogen stream, followed by stirring at 45° C. for about 30 minutes. 19.6g (165mmol) of [Intermediate 8-a] obtained in [Scheme 8-1] and 175 mL of tetrahydrofuran were added dropwise, followed by stirring for about 2 hours. After cooling to 0 °C, 43.6 g (199 mmol) of 4-bromo benzoyl chloride and 350 mL of tetrahydrofuran were added dropwise, and the temperature was raised to 45 °C, followed by stirring for about 2 hours. After cooling to 0°C, an aqueous ammonium chloride solution was added until weakly acidic, and the resulting solid was filtered and washed with methanol after stirring at room temperature to obtain 29g of [Intermediate 9-a]. (Yield 48%)

Synthesis Example 9-2) Synthesis of [Intermediate 9-b]

[Scheme 9-2]

[Intermediate 9-b]

In a round-bottom flask, 8.3 g (34 mmol) of [Intermediate 1-c] obtained from [Scheme 1-3], 11.8 g (37 mmol) of a compound represented by [Intermediate 1-b] obtained from [Scheme 1-2] ), tetrakis (triphenylphosphine) palladium 1.6 g (1 mmol), potassium carbonate 14.0 g (101 mmol), 1,4-dioxane 45 ml, toluene 45 ml, distilled water 20 ml were added and stirred under reflux overnight. When the reaction was completed, extraction was performed using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure, adsorbed on silica gel, and separated by column chromatography using dichloromethane and acetone to obtain 6.0 g of [Intermediate 9-b]. (Yield 50%)

Synthesis Example 9-3) Synthesis of [Compound 9]

[Reaction Scheme 9-3]

[Compound 9]

In a round-bottom flask, 5.4 g (15 mmol) of [Intermediate 9-b] obtained from [Scheme 9-2] and 6.6 g (18 mmol) of the compound represented by [Intermediate 9-a] obtained from [Scheme 9-1] ), tris(dibenzylidineacetone)dipalladium (0) 0.3g (1 mmol), tri-tertiary-butylphosphonium tetrafluoroborate 0.4g (1 mmol), sodium-tertiary-butoxide 0.4g ( 30mmol), ortho-xylene 30mL was added and stirred under reflux for about 5 hours. The reaction solution was concentrated under reduced pressure, methanol was added, and the resulting crystals were filtered. Separated by column chromatography and recrystallized from toluene and methanol to obtain 2.7 g of [Compound 9]. (Yield 28%)

MS (MALDI-TOF): m/z 643 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

104.8,105.4,109.5,109.9,111.6,114.1,116.8,118.9,119.3,119.4,119.8,121.3,121.4,125.5,126.6,127,127.5,128,128.1,128.3,128.7,129,129.2,129.3,131.5,131.8,134,135.5,136.8, 138.7,141.6,143.7,145.4,145.9,150,155.8,161 [46C]

Synthesis Example 10. Synthesis of Compound 10

Synthesis Example 10-1) Synthesis of [Intermediate 10-a]

[Scheme 10-1]

[Intermediate 10-a]

At room temperature, 14.3 g (589 mmol) of magnesium, 3 iodine, and 60 mL of tetrahydrofuran were added to a round-bottom flask A under a nitrogen stream, followed by stirring for about 10 minutes. In a flask immersed in water, 125.9 g (540 mmol) of 4-bromobiphenyl and 240 mL of tetrahydrofuran were added dropwise, followed by reflux stirring for about 2 hours. After 2 hours, the temperature was set to room temperature. At room temperature, 30.0 g (246 mmol) of [Intermediate 8-a] synthesized in [Scheme 8-1] and 150 mL of tetrahydrofuran were added to another round-bottom flask B under a flow of nitrogen and stirred. At room temperature, the reaction solution prepared in flask A was slowly added dropwise to flask B immersed in water. Then, it was stirred under reflux for about 1 hour. The temperature was set to 0° C., and 34.8 g (368 mmol) of methyl chloroformate was added dropwise, followed by reflux stirring for about 1 hour. The temperature was set to 0° C., an aqueous ammonium chloride solution was added until it became slightly acidic, and the resulting solid was filtered and washed with water and heptane. 51.2 g of [Intermediate 10-a] was obtained. (Yield 69%)

Synthesis Example 10-2) Synthesis of [Intermediate 10-b]

[Scheme 10-2]

[Intermediate 10-b]

Except for the use of [Intermediate 10-a] synthesized in [Scheme 10-1] instead of [Intermediate 8-b] used in [Scheme 8-3], and using the same method as Synthesis Example 8-3 [ Intermediate 10-b] was obtained 16.9g. (Yield 31.1%)

Synthesis Example 10-3) Synthesis of [Intermediate 10-c]

[Reaction Scheme 10-3]

[Intermediate 10-c]

Except for the use of [Intermediate 10-b] synthesized in [Scheme 10-2] instead of [Intermediate 8-c] used in [Scheme 8-4], and using the same method as in Synthesis Example 8-4 [ Intermediate 10-c] was obtained 17.2g. (Yield 79.8%)

Synthesis Example 10-4) Synthesis of [Compound 10]

[Scheme 10-4]

[Compound 10]

Using the same method as in Synthesis Example 8-5, except that [Intermediate 10-c] synthesized in [Scheme 10-3] was used instead of [Intermediate 8-d] used in Synthesis Example 8-5). Compound 10] was obtained 5.2g. (Yield 25%)

MS (MALDI-TOF): m/z 643 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103,104.8,109.5,109.9,111.6,116.8,118.9,119.3,119.4,119.8,121.3,121.4,125.5,126.6,127,127.2,127.6,127.9,128,128.3,129,129.2,129.3,130.7,133,133.1,134,138.7,140.8,141.6,143.7, 144.4,145.9,150,155.8,161 [46C]

Synthesis Example 11. Synthesis of Compound 11

Instead of phenyl magnesium bromide (3.0M in Et ₂ O) used in [Scheme 8-2] of Synthesis Example 8-2), (2-fluoro[1,1'-biphenyl]-4-) magnesium bromide (0.5 Except for using M in THF), 3.9 g of [Compound 11] was synthesized using the same method as in Synthesis Example 8-2) to Synthesis Example 8-5). (Yield 32%)

MS (MALDI-TOF): m/z 661 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103,104.8,109.5,109.9,111.6,116.4,116.8,118.9,119.3,119.4,119.8,121.3,121.4,123.6,125.5,126.6,127,127.6,127.9,128,128.3,129,129.2,129.3,130,133,133.1,133.5,134,136.5,138.7,141.6, 143.7,144.4,145.9,150,155.8,159.2,161 [46C]

Synthesis Example 12. Synthesis of Compound 12

Using (4-benzylphenyl) magnesium bromide (0.5M in 2-methyltetrahydrofuran) instead of phenyl magnesium bromide (3.0M in Et ₂ O) used in [Scheme 8-2] of Synthesis Example 8-2) Except for Synthesis Example 8-2) to Synthesis Example 8-5) 3.6g of [Compound 12] was synthesized using the same method. (Yield 30%)

MS (MALDI-TOF): m/z 657 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

41.3,103,104.8,109.5,109.9,111.6,116.8,118.9,119.3,119.4,119.8,121.3,121.4,125.5,126.2,126.3,126.6,127,128,128.2,128.3,128.7,129,129.2,129.3,133,133.1,134,138.7,141.5,141.6, 143.7,144.4,145.9,150,155.8,161 [47C]

Synthesis Example 13. Synthesis of Compound 13

Synthesis Example 13-1) Synthesis of [Intermediate 13-a]

[Scheme 13-1]

[Intermediate 13-a]

Synthesis Example 10-1, except that pentadeutereobromobenzene was used instead of 4-bromobiphenyl used in [Scheme 10-1] of Synthesis Example 10-1), and dimethyl carbonate was used instead of methyl chloroformate. 50 g of [Intermediate 13-a] was obtained using the same method as described above. (Yield 73%)

Synthesis Example 13-2) Synthesis of [Compound 13]

Synthesis except for those prepared using [Intermediate 13-a] synthesized in Synthesis Example 13-1 instead of [Intermediate 10-a] used in [Scheme 10-2], and used in Synthesis Example 10-3) Using the same method as in Example 10-2) to Synthesis Example 10-4), 4.1 g (yield 38%) of [Compound 13] was obtained.

MS (MALDI-TOF): m/z 572 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

103,104.8,109.5,109.9,111.6,116.8,118.9,119.3,119.4,119.8,121.3,121.4,125.5,125.6,126.6,127,127.5,128,128.3,129,129.3,133,133.1,134,134.4,138.7,141.6,143.7,144.4,145.9,150,155.8, 161 [40C]

Synthesis Example 14. Synthesis of [Compound 14]

Synthesis Example 14-1. Synthesis of [Intermediate 14-a]

[Scheme 14-1]

[Intermediate 14-a]

[Intermediate 14-a] using the same method as in Synthesis Example 3-1, except that methyl 2-amino-3,5-dibromobenzoate was used instead of methyl aminobenzoate used in [Scheme 3-1] ] 78.8g (62% yield) was obtained.

Synthesis Example 14-2. Synthesis of [Intermediate 14-b]

[Scheme 14-2]

[Intermediate 14-b]

[Intermediate 1-b] obtained from [Scheme 14-1] was used instead of [Intermediate 1-c] used in [Scheme 9-2], and [Intermediate 1-b] obtained from [Scheme 1-2] [Intermediate 14-b] 13.5 g was obtained using the same method as in Synthesis Example 9-2), except that 2 times the amount (2.2 equivalents) was used. (Yield 48%)

Synthesis Example 14-3. Synthesis of [Compound 14]

[Scheme 14-3]

[Intermediate 14-c] [Intermediate 14-d] [Compound 14]

[Intermediate 14-c] was synthesized using [Intermediate 14-b] synthesized in [Scheme 14-2] instead of [Intermediate 3-a] used in [Scheme 3-2], and the [Scheme 3- [Intermediate 14-d] was synthesized using [Intermediate 14-c] instead of [Intermediate 3-b] used in [3], and [Intermediate 14] instead of [Intermediate 1-c] used in [Scheme 8-4] Except for using -d], 5.6 g (yield 42%) of [Compound 14] was obtained using the same method as in Synthesis Example 3-2) to Synthesis Example 3-3) and Synthesis Example 8-4).

MS (MALDI-TOF): m/z 800 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

22.9,30.9,104.8,109.9,111.7,112.7,118.5,118.7,118.9,119.3,121.3,122.7,123,124.6,125,125.4,125.5,126,127,127.5,128.3,128.7,129,129.2,129.3,129.8,130.5,131.8,133,137.1,138.7, 140.9,141.6,145.9,149.9,155.6,160 [57C]

Synthesis Example 15. Synthesis of [Compound 15]

[Reaction Scheme 15-1]

[Intermediate 15-a] [Compound 15]

[Intermediate 15-a] was obtained by using 2-bromo-10,11-dihydro-5H-dibenzo[b,f]azepine instead of [Intermediate 1-c] used in [Scheme 8-4]. [Compound] using the same method as in Synthesis Example 8-4) to Synthesis Example 8-5), except that [Intermediate 15-a] was used instead of [Intermediate 8-d] used in Synthesis Example 8-5). 15] 3.6g (30% yield) was obtained.

MS (MALDI-TOF): m/z 595 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

32.3,32.6,104.8,109.9,118.5,118.9,119.3,119.5,121.3,121.7,123,125,125.5,126,127.5,128.3,128.4,128.7,128.9,129.2,129.3,130.2,130.4,131.1,131.8,133,135.5,136.6,138.7, 141.6,145.9,149.9,155.6,160 [42C]

Synthesis Example 16. Synthesis of [Compound 16]

[Scheme 16-1]

[Intermediate 16-a] [Compound 16]

Except that methyl 3-aminonaphthalene-2-carboxylate was used instead of the methyl aminobenzoate used in [Scheme 3-1], it was prepared in the same manner as in Synthesis Example 3-1) to obtain [Intermediate 16-a]. , Using this, 2.4 g (yield 24%) of [Compound 16] was obtained using the same method as in Synthesis Example 3-2) to Synthesis Example 3-5).

MS (MALDI-TOF): m/z 657 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

23,30.9,104.8,107.6,109.9,113.1,115.8,118.9,119.3,121,121.2,121.3,122.7,123.7,124.1,124.2,125,125.5,125.8,125.9,126,126.3,126.7,126.8,127.6,127.9,128.3,129.2, 129.3,130.9,131.7,134.3,134.4,136.5,136.6,138.7,141.6,142,143.1,144.6,145.9 [49C]

Synthesis Example 17. Synthesis of [Compound 17]

[Scheme 17-1]

[중간체 17-a] [화합물 17]

[Intermediate 17-a] [Compound 17]

Except for using methyl 1-aminonaphthalene-2-carboxylate instead of methyl aminobenzoate used in [Scheme 3-1], it was prepared in the same manner as in Synthesis Example 3-1) to obtain [Intermediate 17-a]. , Using this, 2.7 g (yield 26%) of [Compound 17] was obtained using the same method as in Synthesis Example 3-2) to Synthesis Example 3-5).

MS (MALDI-TOF): m/z 657 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

23,30.9,104.8,109.9,113.1,115.8,118.2,118.7,118.9,119.3,120.4,121,121.3,122.7,123.7,124.6,124.8,124.9,125,125.5,125.8,126,126.3,127.6,127.9,128.1,128.3,129.2, 129.3,130.9,132.3,134.3,134.4,136.5,136.6,138.7,140.7,141.6,142,143.1,145.9 [49C]

Synthesis Example 18. Synthesis of [Compound 18]

Synthesis Example 18-1) Synthesis of [Intermediate 18-a]

[Scheme 18-1]

[Intermediate 18-a]

5-bromoindole 50.0 g (255.0 mmol), iodobenzene 10.4 g (510.0 mmol), copper powder 32.4 g (510.0 mmol), 18-crown-6 13.5 g (51.0 mmol), potassium carbonate 105.7 g (765.0 mmol) ) Was added in order, 500 ml of 1,2-dichlorobenzene was added, and then refluxed and stirred at 180° C. for 1 day.

When the reaction was completed, the solution was concentrated under reduced pressure after high-temperature filtering, and the organic layer solution was subjected to column chromatography with hexane to obtain 56.2 g of [Intermediate 18-a]. (Yield 81%)

Synthesis Example 18-2) Synthesis of [Intermediate 18-b]

[Scheme 18-2]

[Intermediate 18-a] [Intermediate 18-b]

After dissolving 56.2 g (206.5 mmol) of the [Intermediate 18-a] compound obtained from [Scheme 18-1] in 600 ml of tetrahydrofuran under a stream of nitrogen, 1.6M normal-butyllithium 155 ml (247.8 mmol) was slowly added dropwise, and when the dropping was completed, the mixture was stirred for 1 hour while maintaining -78°C. Thereafter, 25.8 g (247.8 mmol) of trimethylborate was slowly added dropwise, and the mixture was raised to room temperature and stirred for 2 hours.

Upon completion of the reaction, 300 ml of a 2M aqueous hydrochloric acid solution was added dropwise at room temperature and stirred for 30 minutes. Thereafter, extraction was performed with ethyl acetate and water, the organic layer was concentrated under reduced pressure, and recrystallized with dichloromethane and hexane to obtain 17.9 g of [Intermediate 18-b]. (Yield 56%)

Synthesis Example 18-3) Synthesis of [Intermediate 18-d]

[Scheme 18-3-1]

[Intermediate 18-c-1]

[Scheme 18-3-2]

[Intermediate 18-c-2]

The same as in Synthesis Examples 1-4 to 1-5, except that 4-pyridinyl magnesium bromide (0.25M in THF) was used instead of phenyl magnesium bromide (3.0M in Et ₂ O) used in Synthesis Example 1-4. [Intermediate 18-c-2] was obtained using the method.

Synthesis Example 18-4) Synthesis of [Intermediate 18-d]

[Scheme 18-4]

[Intermediate 18-d]

Instead of [intermediate 1-c] used in [Scheme 1-6], 2-bromo-9H-carbazole was used, and [intermediate 18-c-2] synthesized above was used instead of [intermediate 1-e] 15.8g of [Intermediate 18-d] was obtained using the same method as in Synthesis Example 1-6, except that it was used. (79% yield)

Synthesis Example 18-5) Synthesis of [Compound 18]

[Scheme 18-5]

[Compound 18]

Except for using the synthesized [intermediate 18-d] instead of the synthesized [intermediate 18-b] and [intermediate 1-f] instead of [intermediate 1-b] used in [Scheme 1-7] 4.6 g of [Compound 18] was obtained using the same method as in Synthesis Example 1-7. (Yield 25%)

MS (MALDI-TOF): m/z 564 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

104.8,107.6,109.5,109.9,111.6,116.8,118.9,119.3,119.4,119.8,121.3,121.4,125.5,126.6,127.4,127.7,128.3,128.5,129.3,131.1,132.3,133,133.1,133.6,138.7,140.3, 141.6,143.7,144.4,149.3,149.8,155.8,161 [39C]

Synthesis Example 19. Synthesis of [Compound 19]

Synthesis Example 19-1) Synthesis of [Intermediate 19-a]

[Reaction Scheme 19-1]

[Intermediate 19-a]

57 g of [Intermediate 19-a] was obtained in the same manner as in Synthesis Example 18-1, except that 3-iodopyridine was used instead of the iodobenzene used in [Scheme 18-1]. (Yield 84%)

Synthesis Example 19-2) Synthesis of [Compound 19]

Except for using the synthesized [intermediate 19-a] instead of the [intermediate 18-a] used in [Scheme 18-2], using the same method as in Synthesis Example 18-2 to Synthesis Example 18-5 [ Compound 19] 4.2 g was obtained (yield 24%).

MS (MALDI-TOF): m/z 565 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

102.4,107.6,109.5,109.9,111.6,116.8,118.9,119.2,119.3,119.8,121.3,121.4,124.4,124.7,125.5,126.6,127.4,127.7,128.5,128.7,132.3,132.6,133,133.1,135.5,140.3, 141.5,141.6,143.7,144.4,146.4,149.3,149.8,155.8,161 [38C]

Synthesis Example 20. Synthesis of [Compound 20]

Synthesis Example 20-1) Synthesis of [Intermediate 20-a]

[Reaction Scheme 20-1]

[Intermediate 20-a]

Using 4-bromoindole instead of 6-bromoindole used in [Scheme 1-1], it was prepared in the same manner as in Synthesis Examples 1-1 to 1-2 to obtain 28g of [Intermediate 20-a] . (Yield 62%)

Synthesis Example 20-2) Synthesis of [Intermediate 20-b]

[Scheme 20-2]

[Intermediate 20-b]

Using 4-bromo-9H-carbazole instead of [Intermediate 1-c] used in [Scheme 1-6], 16 g of [Intermediate 20-b] was obtained in the same manner as in Synthesis Example 1-6. (79% yield)

Synthesis Example 20-3) Synthesis of [Compound 20]

[Scheme 20-3]

[Compound 20]

Except for using the synthesized [intermediate 20-a] instead of [intermediate 1-b] used in [Scheme 1-7], and using the synthesized [intermediate 20-b] instead of [intermediate 1-f] Then, 4.5 g of [Compound 20] was obtained using the same method as in Synthesis Example 1-7. (Yield 26%)

MS (MALDI-TOF): m/z 563 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

104.8,108.4,109.5,117.6,118.9,119.8,121.3,121.4,125.5,125.6,125.7,126.6,127.4,127.5,127.7,128.5,128.6,128.7,129.2,129.3,129.8,131.8,132.3,133,138.7,144.4, 145.9,149.3,155.8,161 [40C]

Synthesis Example 21. Synthesis of [Compound 21]

[Scheme 21-1]

[Compound 21]

[Intermediate 20-b] obtained from [Scheme 20-2] 6.8 g (15.0 mmol), indole 3.7 g (32.0 mmol), tris (dibenzylideneacetone) dipalladium 0.6 g (1.0 mmol), 1 ,1`-bis(diphenylphosphino)ferrocene 0.4 g (1.0 mmol), sodium tertiary butoxide 6.2 g (65.0 mmol) and toluene 120 mL were added, followed by refluxing and stirring for 24 hours. When the reaction is finished, the temperature is adjusted to room temperature and the crystal is filtered. The crystal was recrystallized from dichloromethane and acetone to obtain 3.8 g (yield 52%) of [Compound 21].

MS (MALDI-TOF): m/z 487 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

98.6,104.8,106.3,109.5,111.9,119.8,120.7,120.8,121.4,125.5,125.7,126.6,127.4,127.5,127.7,128.5,128.7,129.2,129.4,131.8,132.3,132.4,133,134.7,144.4,149.3, 155.8,161 [34C]

Synthesis Example 22. Synthesis of [Compound 22]

[Scheme 22-1]

[Intermediate 22-a] [Compound 22]

[Compound 22] in the same manner as in Synthesis Example 21, except that [Intermediate 22-a] prepared in Synthesis Example 3 was used instead of [Intermediate 20-b] used in [Scheme 21-1]. I got 4.3 g. (Yield 54%)

MS (MALDI-TOF): m/z 529 [M] ⁺ . ¹³ C NMR (75 MHz, CDCl ₃ ) δ:

22.3,30.9,104.8,109.5,111.7,112.3,114.4,116,118.5,118.7,119.8,120.2,120.7,122.9,125,125.4,125.8,126.6,127.5,128.3,128.7,129,129.2,129.4,130.5,131.4,131.8,131.9, 133.9,134.7,137.1,149.2,155.6,160 [37C]

Example 1 to 22

Fabrication of organic light emitting diodes

The ITO glass was patterned so that the light emitting area was 2 mm x 2 mm, and washed. After mounting the substrate in the vacuum chamber, the base pressure is 1x10 ^-6 torr, and then the organic material is placed on the ITO DNTPD (700Å), α-NPB (300Å), compounds 1 to 22 (90%) prepared by the present invention + (piq) ₂ Ir(acac) (10%) (300Å), Alq ₃ (350Å), LiF (5Å), and Al (1,000Å) were formed in the order, and the measurement was performed at 0.4 mA.

The structures of the DNTPD (700Å), α-NPB, (piq) ₂ Ir(acac), Alq ₃ and [Compound 1] to [Compound 22] are as follows.

[DNTPD] [α-NPB]

[(piq) ₂ Ir(acac)] [Alq ₃ ]

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20] [Compound 21]

[Compound 22]

Example 23

In the device structures of Examples 1 to 22, [Compound 1] was used for the light emitting layer, and [PTOEP] was used instead of [(piq) ₂ Ir(acac)], and the structure of [PTOEP] was It is as follows.

[PTOEP]

Comparative example One

The organic light emitting device for the comparative example was fabricated in the same manner, except that CBP, which is widely used as a general phosphorescent host material, was used instead of the compound prepared by the present invention in the device structure of the above example, and the structure of the CBP is as follows.

[CBP]

Comparative example 2 to 5

The organic light emitting devices for Comparative Examples 2 to 5 were fabricated in the same manner, except that the following [Compound 23] to [Compound 26] were used instead of the compound prepared by the present invention in the device structures of Examples 1 to 22. Its structure is as follows.

[Compound 23] [Compound 24] [Compound 25]

[Compound 26]

Comparative example 6

The organic light-emitting device for Comparative Example 6 was fabricated in the same manner, except that [Compound 23] was used instead of [Compound 1] prepared by the invention in the device structure of Example 23.

For the organic electroluminescent devices manufactured according to Examples 1 to 23 and Comparative Examples 1 to 6, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T90 refers to the time it takes for the luminance to decrease from the initial luminance (5000nit) to 90%.

[Table 1]

As shown in Table 1, the organic compound secured by the present invention has a much lower driving voltage, higher luminous efficiency, and a longer life than CBP among host materials commonly used as phosphorescent host materials.

In addition, Fig. 2 shows the results of life evaluation (T90 value) of Comparative Example 2, Example 1, and Example 8. As can be seen in Table 1 and Figure 2, it can be seen that the lifespan is further improved even more than the case where deuterium is not substituted when deuterium is substituted as in Example 8, indicating high applicability as an organic light emitting device with a long life. have.

Claims (16)

An organic light-emitting compound represented by the following [Chemical Formula A] or [Chemical Formula B].
[Formula A]

[Formula B]

In the above [Formula A] and [Formula B],
The A ₁ to A ₄ and R ₁ to R ₁₆ are each the same or different, and independently of each other, 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 cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted and hetero atom O, It is any one selected from a C2-C50 heteroaryl group, a cyano group, a nitro group, and a halogen group having N or S, and the A ₁ to A ₄ and R ₁ to R ₈ are each connected with a substituent adjacent to each other Can form an alicyclic, aromatic monocyclic or polycyclic ring, and the formed alicyclic, aromatic monocyclic or polycyclic carbon atoms may be substituted with any one or more heteroatoms selected from N, S, and O;
L ₁ and L ₂ are a linking group, a single bond, 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;
X is a linking group, or a single bond or -C(R ₃₁ R ₃₂ )-, NR ₃₃ , O, S, SiR ₃₄ R ₃₅ , GeR ₃₆ R ₃₇ , PR ₃₈ , PR ₃₉ (=O), C=O, BR ₄₀ ,
R ₃₁ to R ₄₀ are the same as defined in R ₁ to R ₁₆ ;
M, n, n'and p are each independently 1 to Is an integer of 2,
When m, n, n'and p are each 2, each linking group and indole group are the same or different from each other;
In Formula A, p of R ₅ to R ₈ and one of R ₁₀ to R _13, R ₁₅ and R ₁₆ are each a single bond connected to L ₂ ,
In Formula B, p of R ₅ to R ₈ is a single bond connected to L ₂ ;
The'substituted' in the'substituted or unsubstituted' is deuterium, a cyano group, a halogen group, a nitro 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, and 7 to 24 arylalkyl group, C 2 to C 24 heteroaryl group, C 2 to C 24 heteroarylalkyl group, C 1 to C 24 alkoxy group, C 1 to C 24 alkylsilyl group, C 6 It means substituted with one or more substituents selected from the group consisting of an arylsilyl group having 6 to 24 carbon atoms and an aryloxy group having 6 to 24 carbon atoms.
However, 13 compounds represented by the following structures are excluded.

The method of claim 1,
The linking groups L ₁ and L ₂ of the [Chemical Formula A] and [Chemical Formula B] are the same or different, and each independently, a single bond, or an organic light-emitting compound, characterized in that any one selected from the following Structural Formulas 1 to 8 .
[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural Formula 5] [Structural Formula 6] [Structural Formula 7] [Structural Formula 8]

In the substituents L ₁ and L ₂ , hydrogen or deuterium is bonded to the carbon site of the aromatic ring. The method of claim 1,
The substituents A ₁ to A ₄ and R ₁ to R ₁₆ of [Chemical Formula A] and [Chemical Formula B] are the same or different, and independently of each other, hydrogen and deuterium; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; one selected from among, and m, n, n'and p are 1 The method of claim 1,
The organic light-emitting compound represented by [Formula A] or [Formula B] is represented by any one selected from [Formula 1] to [Formula 10].

[Formula 1] [Formula 2]

[Formula 3] [Formula 4]

[Formula 5] [Formula 6]

[Formula 7] [Formula 8]

[Formula 9] [Formula 10]
In the [Formula 1] to [Formula 10], substituents A ₁ to A ₄ and R ₁ to R ₁₆ , R ₃₃ to R ₃₈ , L ₁ , L ₂ , n, n'and p are each the same as defined in claim 1, but one of R ₁₀ to R ₁₆ is a single bond bonded to the linking group L ₂ . The method of claim 1,
The substituents R ₁ to R ₈ An organic light-emitting compound, characterized in that each is connected with a substituent adjacent to each other to form a ring The method of claim 1,
The organic light emitting compound represented by [Formula A] or [Formula B] is represented by any one selected from [Formula 11] to [Formula 22].
[Formula 11] [Formula 12]

[Formula 13] [Formula 14]

[Formula 15] [Formula 16]

[Formula 17] [Formula 18]

[Formula 19] [Formula 20]

[Formula 21] [Formula 22]

Substituents A ₁ to A ₄ and R ₁ to R ₁₆ , X, in the [Formula 1] to [Formula 22] L ₁ , L ₂ , m, n, n'and p are each the same as defined in claim 1, but one of R ₁₀ to R ₁₆ is a single bond bonded to the linking group L _2, and Ra and Rb are the first The same as defined in R ₁ to R ₁₆ in item _{1 ,} j is an integer of 1 to 6, and when j is 2 or more, each Ra can be the same or different and each Rb can be the same or different. The method of claim 1,
The substituent R ₉ of the [Formula A] and [Formula B] is an organic light-emitting compound, characterized in that it is a functional group containing deuterium or deuterium The method of claim 1,
The organic light emitting compound, characterized in that the substituents A ₁ to A ₄ of [Chemical Formula A] and [Chemical Formula B] are each hydrogen or deuterium The method of claim 8,
The linking groups L ₁ and L ₂ are the same or different, and each independently, is a single bond,

or

And, X is a single bond, n, n'and p are each 1, characterized in that the organic light-emitting compound The method of claim 1,
The compound represented by [Formula A] or [Formula B] is any one of the following [Compound 2] to [Compound 20], [Compound 22] to [Compound 126], [Compound 128] to [Compound 130] Organic light-emitting compound as a feature

[Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20]

[Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41] [Compound 42]

[Compound 43] [Compound 44] [Compound 45]

[Compound 46] [Compound 47] [Compound 48]

[Compound 49] [Compound 50] [Compound 51]

[Compound 52] [Compound 53] [Compound 54]

[Compound 55] [Compound 56] [Compound 57]

[Compound 58] [Compound 59] [Compound 60]

[Compound 61] [Compound 62] [Compound 63]

[Compound 64] [Compound 65] [Compound 66]

[Compound 67] [Compound 68] [Compound 69]

[Compound 70] [Compound 71] [Compound 72]

[Compound 73] [Compound 74] [Compound 75]

[Compound 76] [Compound 77] [Compound 78]

[Compound 79] [Compound 80] [Compound 81]

[Compound 82] [Compound 83] [Compound 84]

[Compound 85] [Compound 86] [Compound 87]

[Compound 88] [Compound 89] [Compound 90]

[Compound 91] [Compound 92] [Compound 93]

[Compound 94] [Compound 95] [Compound 96]

[Compound 97] [Compound 98] [Compound 99]

[Compound 100] [Compound 101] [Compound 102]

[Compound 103] [Compound 104] [Compound 105]

[Compound 106] [Compound 107] [Compound 108]

[Compound 109] [Compound 110] [Compound 111]

[Compound 112] [Compound 113] [Compound 114]

[Compound 115] [Compound 116] [Compound 117]

[Compound 118] [Compound 119] [Compound 120]

[Compound 121] [Compound 122] [Compound 123]

[Compound 124] [Compound 125] [Compound 126]

[Compound 128] [Compound 129] [Compound 130] A first electrode;
A second electrode facing the first electrode; And
An organic light-emitting device comprising; an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one organic light-emitting compound of any one selected from claims 1 to 10. The method of claim 11,
The organic layer is an organic light emitting device comprising at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 12,
The organic layer interposed between the first electrode and the second electrode includes a light emitting layer,
The light-emitting layer is an organic light-emitting device comprising a host and a dopant, and the organic light-emitting compound is used as a host. The method of claim 13,
The organic layer is an organic light emitting device, characterized in that it further comprises a hole blocking layer or an electron blocking layer. The method of claim 12,
An organic light-emitting device, characterized in that at least one layer selected from each of the layers is formed by a deposition process or a solution process. The method of claim 11,
The organic light emitting device may include a flat panel display device; Flexible display device; Monochrome or white flat lighting devices; And, a single color or white flexible lighting device; organic light emitting device characterized in that used in any one device selected from

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