KR20230054898A - Organic compounds for organic electroluminescent devices and organic electroluminescent devices - Google Patents

Abstract

The present application provides organic compounds, applications thereof, and organic electroluminescent devices including the same. The organic compound has a structure represented by Formula (1), X ¹ and X ² are each independently selected from CR ¹ R ² , NR ³ , O, S, or SiR ⁴ R ⁵ ; any one of R ¹ to R ⁵ forms a ring together with ring A or ring D; Ring A, ring D, and ring E are each independently one selected from a C5 to C30 aromatic ring and a C3 to C30 aromatic hetero ring, and at least one has a structure represented by formula (a), represented by formula (a) structure is condensed through ring F; ring F and ring G are each independently selected from a C5 to C23 aromatic ring and a C3 to C23 aromatic heterocyclic ring; Y ¹ and Y ² are each independently selected from CR ⁶ R ⁷ , NR ⁸ , O, S, or SiR ⁹ R ¹⁰ ; R ¹ to R ¹⁰ are independently hydrogen, halogen, cyano, nitro, hydroxyl, C1 to C10 chain alkyl, C3 to C10 cycloalkyl, C1 to C10 alkoxy, amino, C1 to C10 silyl, C6 to C30 aryl, It is one selected from C3 ~ C30 heteroaryl.

Description

Organic compounds for organic electroluminescent devices and organic electroluminescent devices

The present invention relates to the field of organic light emitting materials, and specifically, to organic compounds, applications thereof, and organic electroluminescent devices including the same.

Recently, optoelectronic devices based on organic materials have become increasingly popular. Because organic materials are very suitable for manufacturing flexible substrates due to their inherent flexibility, beautiful and wonderful optoelectronic products can be designed and produced according to requirements, and advantages incomparable with inorganic materials can be obtained. Examples of organic optoelectronic devices of this type include organic light emitting diodes (OLEDs), organic field effect transistors, organic photovoltaic cells and organic sensors, and the like. Among them, OLED has developed particularly rapidly and has already achieved commercial success in the field of information display. Since OLED can provide three colors with high saturation, red, green, and blue, full-color display devices made with OLED do not require a separate backlight, have beautiful colors, and are thin and flexible.

The core of an OLED device is a thin film structure containing various organic functional materials. Common functionalized organic materials include hole injecting materials, hole transporting materials, hole blocking materials, electron injecting materials, electron transporting materials, electron blocking materials, light emitting host materials, and light emitting guests (dyes). During energization, electrons and holes are respectively injected and transported to the light emitting region and recombine in the light emitting region to generate excitons and emit light.

People have developed various organic materials that can improve the carrier mobility, control the carrier balance, break through the electroluminescence efficiency, and delay the device decay by combining with various exotic device structures. For reasons of quantum mechanics, general fluorescent emitters mainly emit light using singlet excitons generated when electrons and holes combine, and this is still widely applied to various OLED products. Some metal complexes, such as iridium complexes, can emit light by simultaneously using triplet excitons and singlet excitons, which are called phosphorescent emitters, and their energy conversion efficiency can be four times higher than conventional fluorescent emitters. Thermally activated delayed fluorescence (TADF) technology promotes the conversion of triplet excitons into singlet excitons, so even in the absence of metal complexes, triplet excitons can be effectively used to realize high luminous efficiency. Thermally activated sensitive fluorescence (TASF) technology can also realize high luminous efficiency by using materials having TADF properties to sensitize a light emitting body through an energy transfer method.

Recently, according to a certain literature, TADF (Thermally Activated Delayed Fluorescence)-based ultrapure blue fluorescent compounds C1 and C2 having a B-N resonance structure have been reported, and these types of compounds are rigid with B, N and benzene rings. make up the polycyclic aromatic backbone. The nitrogen atom has a resonance effect opposite to that of the boron atom, and the opposite resonance effect is enhanced at the para position. Therefore, this effect has a constant TADF characteristic since the HOMO and LUMO orbitals can be clearly separated.

As OLED products gradually enter the market, people's requirements for this type of product are getting higher and higher. Currently used OLED materials and device structures cannot completely solve problems such as OLED product efficiency, lifetime, and cost. This problem is particularly noticeable in deep blue light devices.

In view of the above problems of the prior art, an object of the present invention is to provide a novel compound for an organic electroluminescent device, wherein an organic electroluminescent device using this type of compound can emit deep blue light, It can meet the demand for continuous improvement of photoelectric performance and service life. In the present invention, unless otherwise specified, “deep blue light” means light having a wavelength of about 440 nm to 470 nm.

Researchers of the present invention propose clever molecular design methods through serious thinking and continuous experimentation. Surprisingly, the compound obtained through the above solution is very suitable for use in OLED, and the obtained device has excellent performance and can meet people's requirements.

Specifically, one of the objects of the present invention is to provide an organic compound having a structure represented by the following formula (1).

here,

X ¹ and X ² are each independently selected from CR ¹ R ² , NR ³ , O, S or SiR ⁴ R ⁵ ;

When any one or plural of R ¹ to R ⁵ are present, they optionally form a ring together with ring A or ring D;

Ring A, ring D and ring E are each independently one selected from a substituted or unsubstituted C5-C30 aromatic ring and a substituted or unsubstituted C3-C30 aromatic hetero ring, at least one of which is a structure represented by formula (a) And the structure represented by formula (a) is condensed through ring F (formula (1) to form a compound having the structure, i.e., any one or a plurality of rings A, rings D and rings E of the formula (a ), each independently condensed with the parent structure via ring F on formula (a) to form a compound having the structure of formula (1);

ring F and ring G are each independently selected from a substituted or unsubstituted C5 to C23 aromatic ring and a substituted or unsubstituted C3 to C23 aromatic heterocyclic ring;

Y ¹ and Y ² are each independently selected from CR ⁶ R ⁷ , NR ⁸ , O, S or SiR ⁹ R ¹⁰ ;

R ¹ to R ¹⁰ are independently hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1 to C10 chain alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C1 to one selected from C10 alkoxy, amino, substituted or unsubstituted C1 to C10 silyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl;

When a substituent exists in the above group, the substituent is halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, It is one or a combination of two or more selected from amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.

The specific reason why the compound of the present invention has excellent performance as a light emitting material is not yet clear, but it is speculated as follows. The compound having the general formula (1) structure that meets the limitations of the present invention has a rigid conjugated structure suitable as a mother nucleus, connects a specific aromatic group to the mother nucleus through methylene, imine, O or S, etc. Since the conjugated structure between the groups is broken, high external quantum efficiency and low rising and falling voltages can be exhibited in an OLED device. When a compound obtained by linking a specific mother nucleus and a specific aromatic group in the above specific manner is used as a dye for the light emitting layer, the voltage and efficiency of the device can be improved, red shifting of the light color can be prevented, and the purity of the light color can be improved.

In the present invention, the “substituted or unsubstituted” group may be substituted by one substituent or substituted by a plurality of substituents, and in the case of a plurality of substituents, may be selected from different substituents, the same expression is mentioned in the present invention When all of them have the same meaning, the selection ranges of substituents are all as described above, and descriptions are omitted here.

In this specification, the expression of Ca to Cb means that the number of carbon atoms in the group is a to b, and unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms in the substituent.

In this specification, the way of expressing the ring structure drawn with “-” indicates that the linking site is located at any position on the ring structure capable of forming a bond.

In this specification, “each independently” means that when there are multiple subjects, they may be the same or different from each other.

In the present invention, unless otherwise specified, the expression of a chemical element generally includes the concept of isotopes having the same chemical properties, such as the expression “hydrogen (H)”, and ¹ H (protium or H) having the same chemical properties. ), also includes the concept of ² H (deuterium or D); Carbon (C) includes ¹² C, ¹³ C, etc., and the description is omitted here.

In the present invention, the hetero atom generally means an atom or group of atoms selected from N, O, S, P, Si and Se, preferably N, O, and S.

In this specification, examples of halogen include fluorine, chlorine, bromine, iodine and the like.

In the present invention, the single-ring aryl group includes one or at least two phenyl groups in a molecule, and when it includes at least two phenyl groups in a molecule, the phenyl groups are independent of each other and mean that they are connected through a single bond. Typically, phenyl, biphenyl, terphenyl and the like; A condensed ring aryl group means that the molecule contains at least two benzene rings, but the benzene rings are not independent of each other and condensed with each other by sharing a ring edge, and examples thereof include naphthyl, anthracenyl, and the like; The single-ring heteroaryl group contains at least one heteroaryl group in the molecule, and when the molecule contains one heteroaryl group and another group (eg, aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other group are independent of each other, , means connected through a single bond, exemplarily pyridine, furan, thiophene and the like; Condensed-ring heteroaryl means formed by condensation of at least one phenyl group and at least one heteroaryl group, or formed by condensation of at least two heteroaryl rings, and examples thereof include quinoline, isoquinoline, benzofuran, and dibenzofuran. , benzothiophene, and dibenzothiophene.

In the present invention, unless otherwise specified, aryl and heteroaryl include both single rings and condensed rings.

In the present invention, unless otherwise specified, substituents are not condensed with the group on which they are located.

In the organic compound of the present invention, preferably, X ¹ and X ² are each independently selected from NR ³ , O or S. In the organic compound of the present invention, more preferably, at least one of X ¹ and X ² is NR ³ , and R ³ is one of substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

By setting the organic compound of the present invention to the above structure, higher carrier transport performance can be obtained.

In the organic compound of the present invention, preferably, Y ¹ and Y ² are each independently selected from CR ⁶ R ⁷ , NR ⁸ or O; More preferably, at least one of Y ¹ and Y ² is CR ⁶ R ⁷ ; Even more preferably, both Y ¹ and Y ² are CR ⁶ R ⁷ .

In the organic compound of the present invention, preferably, R ⁶ and R ⁷ are each independently hydrogen, substituted or unsubstituted C1 ~ C10 chain alkyl, substituted or unsubstituted C3 ~ C10 cycloalkyl, substituted or unsubstituted C6 ~ C30 aryl, one selected from substituted or unsubstituted C3 ~ C30 heteroaryl;

More preferably, R ⁶ and R ⁷ are each independently hydrogen or one selected from the following groups;

Even more preferably, both R ⁶ and R ⁷ are methyl.

By setting the organic compound of the present invention to the above structure, red shifting of light color can be prevented and the purity of light color can be improved.

In the organic compound of the present invention, ring F is preferably one selected from a substituted or unsubstituted C5-C14 aromatic ring and a substituted or unsubstituted C3-C14 aromatic hetero ring; More preferably, it is one selected from a substituted or unsubstituted C5 ~ C10 aromatic ring and a substituted or unsubstituted C3 ~ C10 N-containing aromatic heterocyclic ring; More preferably, it is a structure represented by formula (b),

Here, * represents the condensed site with the ring where Y ¹ Y ² ring is located, and ring F is condensed with the parent nucleus through Z ¹ and Z ² , Z ² and Z ³ , or Z ³ and Z ⁴ , and Z ^{1 to} Z ⁴ is each independently one selected from C, CR ¹¹ , and N; R ¹¹ are each independently hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1 ~ C10 chain alkyl, substituted or unsubstituted C3 ~ C10 cycloalkyl, substituted or unsubstituted C1 ~ C10 Alkoxy, substituted or unsubstituted C1 ~ C10 silyl, amino, substituted or unsubstituted C6 ~ C30 arylamino, substituted or unsubstituted C3 ~ C30 heteroarylamino, substituted or unsubstituted C6 ~ C30 aryl, substituted or unsubstituted It is one selected from cyclic C3-C30 heteroaryl, wherein R ¹¹ is optionally linked to an adjacent aromatic ring or aromatic hetero ring to form a ring;

Even more preferably, Z ¹ to Z ⁴ are each independently CR ¹¹ , and each R ¹¹ is independently hydrogen or one selected from the following groups.

By setting the organic compound of the present invention to the above structure, higher external quantum efficiency and lower voltage can be exhibited in an OLED device.

In the organic compound of the present invention, ring A, ring D and ring E are each independently selected from a substituted or unsubstituted C5 to C14 aromatic ring and a substituted or unsubstituted C3 to C14 aromatic hetero ring, and at least one has a structure represented by formula (a);

More preferably, ring A and ring D are each independently selected from structures represented by formula (c) or formula (a), ring E is a structure represented by formula (c') or formula (a), At least one of ring A, ring D and ring E has a structure represented by formula (a),

Here, * indicates a site connected to the parent nucleus, Z ⁵ to Z ⁸ are each independently selected from C, CR ¹¹ , and N; R ¹¹ are each independently hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1 ~ C10 chain alkyl, substituted or unsubstituted C3 ~ C10 cycloalkyl, substituted or unsubstituted C1 ~ C10 Alkoxy, substituted or unsubstituted C1 ~ C10 silyl, amino, substituted or unsubstituted C6 ~ C30 arylamino, substituted or unsubstituted C3 ~ C30 heteroarylamino, substituted or unsubstituted C6 ~ C30 aryl, substituted or unsubstituted It is one selected from cyclic C3-C30 heteroaryl, and R ¹¹ is optionally linked to an adjacent aromatic ring or aromatic hetero ring to form a ring;

Even more preferably, at least one of ring A and ring D is a structure represented by formula (a).

Also preferably, Z ⁵ to Z ⁸ are each independently CR ¹¹ , and each R ¹¹ is independently hydrogen or one selected from the following groups.

By setting the organic compound of the present invention to the above structure, higher external quantum efficiency and lower voltage can be exhibited in an OLED device.

In the organic compound of the present invention, ring G is preferably one selected from a substituted or unsubstituted C5-C14 aromatic ring and a substituted or unsubstituted C3-C14 aromatic hetero ring;

More preferably, it is one selected from a substituted or unsubstituted C5 ~ C10 aromatic ring and a substituted or unsubstituted C3 ~ C10 N-containing aromatic heterocyclic ring;

More preferably, it is a structure represented by formula (b'),

Here, * indicates a condensed site with a ring where Y ¹ Y ² ring is located, and Z ^1' to Z ^4' are each independently selected from C, CR ¹² , and N; R ¹² is independently hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1 to C10 chain alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C1 to C10 alkoxy; Substituted or unsubstituted C1 ~ C10 silyl, amino, substituted or unsubstituted C6 ~ C30 arylamino, substituted or unsubstituted C3 ~ C30 heteroarylamino, substituted or unsubstituted C6 ~ C30 aryl, substituted or unsubstituted It is one selected from C3 to C30 heteroaryl, wherein R ¹² is optionally condensed with a connected aromatic ring or aromatic hetero ring to form a ring.

By setting the organic compound of the present invention to the above structure, higher external quantum efficiency and lower voltage can be exhibited in an OLED device.

Examples of C1-C10 alkyl mentioned in the present invention include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-hexyl, n-octyl, n-nonyl.

Examples of C3-C10 cycloalkyl mentioned in the present invention include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclodecyl and the like.

Examples of C1-C10 alkoxy mentioned in the present invention include methoxy, ethoxy, butoxy, hexyloxy, octyloxy and the like.

Examples of C1-C10 thioalkoxy mentioned in the present invention include methylthio, ethylthio, butylthio, hexylthio, octylthio and the like.

Examples of C1-C10 silyl mentioned in the present invention include trimethylsilyl, triethylsilyl and the like.

Examples of C6-C30 arylamino mentioned in the present invention include phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino and the like.

Examples of the C3-C30 heteroarylamino mentioned in the present invention include pyridylamino, pyrimidinylamino, dibenzofurylamino and the like.

C6-C30 aryls mentioned in the present invention include C6-30 single-ring aryls and C10-C30 condensed-ring aryls. Examples of C6-30 single ring aryl include phenyl, biphenyl, terphenyl and the like. Specifically, the biphenyl includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; The terphenyl is p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, and m-terphenyl-2-yl. Examples of C10 to C30 condensed ring aryls include naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, and A derivative group etc. are mentioned. Specifically, the naphthyl includes 1-naphthyl or 2-naphthyl; the anthracenyl is selected from 1-anthracenyl, 2-anthracenyl, and 9-anthracenyl; said fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; said pyrenyl is selected from 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; The naphthacenyl is selected from 1-naphthacenyl, 2-naphthacenyl, and 9-naphthacenyl. The derivative group of fluorene is 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-diphene tylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, spirofluorenyl, and benzofluorenyl.

The C3-C30 heteroaryl mentioned in the present invention includes C3-C30 single-ring heteroaryl and C6-C30 condensed-ring heteroaryl. Examples of C3 to C30 single ring heteroaryl include furyl, thienyl, pyrrolyl, pyridyl and the like. Examples of the C6 to C30 condensed ring heteroaryl include benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl, acridinyl, isobenzofuryl, isobenzothienyl, Acridinyl, pyridyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, etc. are mentioned.

Specific examples of arylene in the present invention include divalent groups obtained by removing one hydrogen atom from the above aryl examples. Specific examples of the heteroarylene in the present invention include a divalent group obtained by removing one hydrogen atom from the examples of the heteroaryl.

Examples of aryloxy in the present invention include monovalent groups composed of the above aryl, heteroaryl, and oxygen.

Examples of C6-C30 arylamino mentioned in the present invention include phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrenylamino, biphenylamino and the like.

Examples of the C3-C30 heteroarylamino mentioned in the present invention include pyridylamino, pyrimidinylamino, dibenzofurylamino and the like.

In the above, the preferred methods of each group have been described, and those skilled in the art can combine them without departing from the gist of the present invention. Below, partial subgeneric formulas of formula (1) are given as examples, but the structure of the compound of the present invention is not limited to these subgeneral formulas.

Even more preferably,

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ego,

Even more preferably,

이다.

am.

In each of the subgeneral formulas, Z ¹¹ to Z ¹⁸ , Z ^5' to Z ^7' have the same ranges as the aforementioned Z ¹ to Z ⁴ , and R ^8' and R ^8'' have the same ranges as the aforementioned R ⁸ . have

Furthermore, the general formula compounds of the present invention are preferably the following specific compounds, but the present invention is not limited to the following specific compounds.

As another aspect of the present invention, the application of the above compound in an organic electroluminescent device is further provided. Specifically, it is preferably used as a light emitting layer material in an organic electroluminescent device.

As another aspect of the present invention, there is further provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer has the above general formula It contains the compound of (1).

The compound of formula (1) of the present invention has a rigid conjugated structure suitable as a parent nucleus, and connects a specific aromatic group to the parent nucleus through methylene, imine, O, or S, etc. At the same time, the conjugated structure between the parent nucleus and the group is broken. , can exhibit high external quantum efficiency and low rising and falling voltages in OLED devices. When a compound obtained by linking a specific mother nucleus and a specific aromatic group in the above specific manner is used as a dye for the light emitting layer, the voltage and efficiency of the device can be improved, red shifting of the light color can be prevented, and the purity of the light color can be improved. The compound according to the scheme is very suitable for application in OLED, and the obtained device has excellent performance and can meet people's needs.

Hereinafter, the technical solutions of the present invention will be further described through specific embodiments of the present invention. Those of ordinary skill in the art will understand that the examples are only for helping understanding of the present invention and should not be regarded as specifically limiting the present invention.

Synthesis Example (1): Synthesis of P1

At room temperature, raw material 1 (20 g, 88.54 mmol), raw material 2 (58 g, 177.07 mmol), bis [di-tert-butyl- (4-dimethylaminophenyl) phosphine] palladium dichloride (II) ( 2.5g, 3.54mmol), sodium tert-butoxide (25.5g, 265.61mmol), xylene (200ml) was added as a solvent, substituted with nitrogen three times, heated to 120 ° C, reacted for 12 hours, and then heated Stopped, filtered and evaporated to dryness, and purified by column chromatography (petroleum ether: dichloromethane = 10: 1) to obtain 55.0 g of product (intermediate M1).

Intermediate M1 (55g, 72.04mmol) was dissolved in 500ml of xylene, and n-butyllithium (86.4ml, 216.12mmol) was slowly added dropwise at -40°C. After activation by heating for a period of time, the temperature was lowered to -40 ° C, BBr ₃ (45.03 g, 180.1 mmol), and DIEA (37.2 g, 288.16 mmol) were added slowly and sequentially, and after returning to room temperature, heated to 110 ° C. After reacting for 10 hours, heating was stopped, washed with water, filtered and evaporated to dryness, and purified by column chromatography (petroleum ether: dichloromethane = 10: 1) to obtain 19.8 g (P1) of a product.

Synthesis Example (2): Synthesis of P16

56.6 g of a product (intermediate M2) was obtained in the same synthesis method as in Synthesis Example (1), except that raw material 2 was replaced with an equivalent amount of raw material 3. The synthesis method of P16 was similar to that of P1, and 19.8 g (P16) of the product was finally obtained.

Synthesis Example (3): Synthesis of P29

28.2 g of a product (intermediate M3) was obtained in the same synthesis method as in Synthesis Example 1, except that raw material 1 was replaced with an equivalent amount of raw material 4. The synthesis method of P29 was similar to that of P1, and 9.87 g (P29) of the product was finally obtained.

Synthesis Example (4): Synthesis of P53

Raw material 1 (10 g, 44.27 mmol), raw material 2 (14.45 g, 44.27 mmol), (DBA) ₃ Pd ₂ (0.81 g, 0.88 mmol), tri-tert-butylphosphine tetrafluoro in a 500 ml three-necked flask at room temperature. Borate (0.51g, 1.77mmol), sodium tert-butoxide (10.62g, 110.68mmol), and toluene (100ml) as a solvent were added, substituted with nitrogen three times, heated to reflux, and reacted for 12 hours. Heating was stopped, filtered and evaporated to dryness, and purified by column chromatography (petroleum ether : dichloromethane = 10: 1) to obtain 15 g of product (intermediate M4).

Intermediate M4 (15 g, 31.75 mmol), raw material 3 (5.4 g, 31.75 mmol), Pd132 (0.45 g, 0.64 mmol), sodium tert-butoxide (7.62 g, 79.4 mmol) as solvent in a 500 ml three-necked flask at room temperature. Xylene (200ml) was added, nitrogen was substituted three times, the temperature was raised to 120 ° C, the reaction was performed for 12 hours, the heating was stopped, filtered and evaporated to dryness, and column chromatography (petroleum ether: dichloromethane = 10: 1) Purification gave 16.7 g of the product (intermediate M5).

Intermediate M5 (16.7g, 27.63mmol) was dissolved in 200ml of xylene, and n-butyllithium (33.2ml, 82.88mmol) was slowly added dropwise at -40°C. After heat activation for 1 hour, the temperature was lowered to -40 °C, BBr ₃ (17.27 g, 69.1 mmol) and DIEA (14.26 g, 110.52 mmol) were added slowly and sequentially, returned to room temperature and heated to 110 °C. After reacting for 10 hours, heating was stopped, washed with water, filtered and evaporated to dryness, and purified by column chromatography (petroleum ether: dichloromethane = 20: 1) to obtain 6.78 g (P53) of a product.

Synthesis Example (5): Synthesis of Material 54

11.3 g of a product (intermediate M6) was obtained by the same synthesis method as in Synthesis Example (4), except that raw material 5 was replaced with an equivalent amount of raw material 6. The synthesis method of P54 was similar to that of P53, and finally 4.6 g of product (P54) was obtained.

Synthesis Example (6): Synthesis of P84

Intermediate M4 (10 g, 21.17 mmol), raw material 7 (5.96 g, 21.17 mmol), Pd132 (0.3 g, 0.42 mmol), sodium tert-butoxide (5.1 g, 52.93 mmol) as solvent in a 500 ml three-necked flask at room temperature. Xylene (200ml) was added, nitrogen was substituted three times, the temperature was raised to 120 ° C, the reaction was performed for 12 hours, the heating was stopped, filtered and evaporated to dryness, and column chromatography (petroleum ether: dichloromethane = 10: 1) Purification gave 10.8 g of the product (intermediate M7).

Intermediate M7 (10.8g, 15.60mmol) was dissolved in 100ml of xylene, and n-butyllithium (18.12ml, 45.29mmol) was slowly added dropwise at -40°C. After heat activation for 10 hours, the temperature was lowered to -40 °C, BBr ₃ (9.75 g, 39 mmol) and DIEA (8.04 g, 62.4 mmol) were added slowly and sequentially, and after returning to room temperature, heated to 110 °C for 10 After reacting for an hour, heating was stopped, washed with water, filtered and evaporated to dryness, and purified by column chromatography (petroleum ether: dichloromethane = 10: 1) to obtain 4.2 g of a product (P84).

Synthesis Example (7): Synthesis of P96

Raw material 1 (10 g, 44.27 mmol), raw material 3 (16.94 g, 44.27 mmol), (DBA) ₃ Pd ₂ (0.81 g, 0.88 mmol), tri-tert-butylphosphine tetrafluoro in a 500 ml three-necked flask at room temperature. Borate (0.51g, 1.77mmol), sodium tert-butoxide (10.62g, 110.68mmol), and toluene (100ml) as a solvent were added, substituted with nitrogen three times, heated to reflux, and reacted for 12 hours. , The heating was stopped, filtered and evaporated to dryness, and purified by column chromatography (petroleum ether : dichloromethane = 10: 1) to obtain the product 18.2g (intermediate M8).

Intermediate M8 (18.2g, 34.43mmol), starting material 7 (9.62g, 34.43mmol), Pd132 (0.49g, 0.69mmol), sodium tert-butoxide (8.26g, 86.08mmol), solvent in a 500ml three-necked flask at room temperature After adding xylene (200ml) as a solution, purging with nitrogen three times, raising the temperature to 120 ° C and reacting for 12 hours, stopping the heating, filtering and evaporating to dryness, column chromatography (petroleum ether: dichloromethane = 10: 1) to obtain 19.56 g of product (intermediate M9).

Intermediate M9 (19.56 g, 37.01 mmol) was dissolved in 200 ml of xylene, and n-butyllithium (44.41 ml, 111.03 mmol) was slowly added dropwise at -40 ° C. After heat activation for 1 hour, the temperature was lowered to -40 °C, BBr ₃ (23.13 g, 92.53 mmol) and DIEA (19.10 g, 148.04 mmol) were added slowly and sequentially, returned to room temperature and heated to 110 °C. After reacting for 10 hours, heating was stopped, washed with water, filtered and evaporated to dryness, and purified by column chromatography (petroleum ether: dichloromethane = 20: 1) to obtain 8.6 g of product (P96).

Molecular Structure Theoretical Calculation

In the present invention, quantum chemical calculations are performed for compounds using Gaussian03, and theoretical calculations are performed for P1, P16, P29, P53, P54, P84, P96, and C1, C2, respectively, using the time-dependent density functional method. The calculation results are shown in Table 1.

Here, the structural formulas of compounds C1 and C2 are as follows.

material number First singlet energy level/eV First triplet energy level/eV First singlet oscillator strength C1 3.05 2.5748 0.1771 C2 2.83 2.4166 0.2096 P1 3.07 2.5758 0.2134 P16 3.04 2.5917 0.2073 P29 3.03 2.5836 0.2066 P53 2.92 2.4862 0.2035 P54 3.01 2.5935 0.2114 P84 3.02 2.5845 0.2102 P96 2.99 2.5861 0.2089

The fluorescence emission wavelength of a material is related to the first singlet energy level, and the higher the energy level, the shorter the fluorescence emission wavelength of the material, and the more bluish the emission is. The phosphorescence emission wavelength of the material is related to the first triplet energy level, and the higher the energy level, the shorter the phosphorescence emission wavelength of the material, and the more bluish the emission is. The light-emitting efficiency of a material is related to the first singlet oscillator intensity, and the higher the value of the first singlet oscillator intensity, the higher the light-emitting efficiency of the material. From the calculation results, it can be seen that the material of the present invention still maintains a high first singlet energy level and a high first triplet energy level after condensing a rigid aromatic ring outside the saturated six-membered ring, which is close to the reference material C1. there is. The material C1 has the same exciton energy level as the compound of the present invention, but the first singlet oscillator intensity is relatively low, so the luminous efficiency may be relatively low. On the other hand, material C2 forms a substantially large conjugated structure after condensing an aromatic ring outside the 5-membered ring, and has a lower first singlet energy level than the compound of the present invention, so that the emission wavelength can be longer, requiring a deep blue light device. cannot meet the

Device Example

An OLED includes a first electrode, a second electrode, and an organic material layer positioned between the electrodes. The organic material layer may also be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.

In a specific embodiment, a substrate may be used under the first electrode or over the second electrode. The substrates are all glass or polymer materials excellent in mechanical strength, thermal stability, water resistance, and transparency. In addition, a thin film transistor (TFT) may be provided on the display substrate.

The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO ₂ ), zinc oxide (ZnO), or any combination thereof may be used. can When the first electrode is used as a cathode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg -In), a metal or alloy such as magnesium-silver (Mg-Ag) or any combination thereof may be used.

The organic material layer may be formed on the electrode by a method such as a thermal vacuum deposition method, a spin coating method, or a printing method. The compound used for the organic material layer may be a small organic molecule, an organic high molecule or polymer, or a combination thereof.

The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a single-layer hole transport layer (HTL) including a single-layer hole transport layer containing only one compound and a single-layer hole transport layer containing various compounds. The hole transport region may have a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); Here, the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the light emitting layer.

The material of the hole transport region is a phthalocyanine derivative such as CuPc, a conductive polymer or polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene). sulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly(4-styrenesulfonate) (Pani/PSS), as HT-1 to HT-51 below. aromatic amine derivatives such as the compounds indicated; or any combination thereof, but is not limited thereto.

The hole injection layer is positioned between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of various compounds. For example, the hole injection layer may use one or a plurality of compounds of the above HT-1 to HT-51 or one or a plurality of compounds of the following HI-1 to HI-3; One or a plurality of compounds of HT-1 to HT-51 doped with one or a plurality of compounds of HI-1 to HI-3 may also be used.

The light emitting layer may include a light emitting dye capable of emitting a different wavelength spectrum (ie, a dopant) and may include a host material. The light emitting layer may be a single color light emitting layer that emits a single color such as red, green, and blue. Monochrome light emitting layers of various colors may be arranged in a plane according to a pixel pattern, and may be laminated together to form a colored light emitting layer. When light-emitting layers of different colors are laminated together, they may be spaced apart or connected to each other. The light emitting layer may be a monochromatic light emitting layer capable of simultaneously emitting different colors such as red, green and blue.

According to different techniques, different materials such as fluorescent electroluminescent materials, phosphorescent electroluminescent materials, thermally activated delayed fluorescent light emitting materials and the like can be used as the light emitting layer material. A single light emitting technology may be used in one OLED device, or a combination of various light emitting technologies may be used. These different luminescent materials classified by technology can emit light of the same color or different colors.

In one aspect of the present invention, the light emitting layer uses fluorescence electroluminescence technology. The fluorescent host material of the light emitting layer may be one selected from BFH-1 to BFH-17 listed below, or a combination of a plurality thereof, but is not limited thereto.

In one aspect of the present invention, the light emitting layer uses thermally activated delayed fluorescence emission technology. The host material of the light emitting layer may be one selected from PH-1 to PH-85, or a combination thereof, but is not limited thereto.

In one aspect of the present invention, the light emitting layer may use a thermally activated delayed fluorescence emission technology. The fluorescent dopant of the light emitting layer may be one selected from TDE1 to TDE37 listed below, or a combination of a plurality thereof, but is not limited thereto.

In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may use one or a plurality of compounds of HT-1 to HT-51, but is not limited thereto, or one or a plurality of compounds of PH-47 to PH-77 may be used, but is not limited thereto ; A mixture of one or a plurality of compounds of HT-1 to HT-51 and one or a plurality of compounds of PH-47 to PH-77 may be used, but is not limited thereto.

The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be a single-layer electron transport layer (ETL) including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing various compounds. The electron transport region may have a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

In one aspect of the present invention, the electron transport layer material may be one or a combination of plural selected from ET-1 to ET-65 listed below, but is not limited thereto.

In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may use one or a plurality of compounds of ET-1 to ET-65, but is not limited thereto, or one or a plurality of compounds of PH-1 to PH-46, but is not limited thereto; A mixture of one or a plurality of compounds of ET-1 to ET-65 and one or a plurality of compounds of PH-1 to PH-46 may be used, but is not limited thereto.

The device may further include an electron injection layer positioned between the electron transport layer and the cathode, and the electron injection layer material is LiQ, LiF, NaCl, CsF, Li ₂ O, Cs ₂ CO ₃ , BaO, Na, Li, Ca, one or a combination of Mg and Yb, but is not limited thereto.

The manufacturing process of the organic electroluminescent device in the following examples is as follows.

Example 1

A glass plate coated with an ITO transparent conductive layer was sonicated with a commercially available cleaner, rinsed with deionized water, ultrasonically degreased with an acetone:ethanol mixed solvent, fired in a clean environment until moisture was completely removed, UV light and ozone and bombarded the surface with a low-energy positive ion beam;

The glass substrate with an anode was placed in a vacuum chamber, vacuumed to less than 1×10 ^-5 Pa, and 10 nm of HT-4:HI-3 (97/3, w as a hole injection layer on the anode layer film). /w) mixture, compound HT-4 of 60 nm as hole transport layer, compound HT-14 of 5 nm as electron blocking layer, compound BFH-4:P1 (100:3, w/w) of 20 nm as light emitting layer binary mixture, hole blocking 5 nm of ET-23 as a layer, 25 nm of a compound ET-61:ET-57 (50/50, w/w) mixture as an electron transport layer, 1 nm of LiF as an electron injection layer, and 150 nm of metal aluminum as a cathode were sequentially heated. vacuum deposited. The total deposition rate of all organic layers and LiF was controlled to 0.1 nm/sec, and the deposition rate of the metal electrode was controlled to 1 nm/sec.

Examples 2 to 22 and Comparative Examples 1 to 2

Examples 2 to 22 and Comparative Examples 1 to 2 (replacing P1 with compounds C1 and C2, respectively) in the same manner as in Example 1, except that P1 in Example 1 was replaced with the corresponding compound in Table 2. An organic electroluminescent device was obtained.

The following performance measurements were performed on the organic electroluminescent device manufactured through the above process.

The driving voltage and external quantum efficiency (EQE) of the organic electroluminescent devices prepared in Examples 1 to 22 and Comparative Examples 1 to 2 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage when the luminance of the organic EL device reached 1000 cd/m ² by raising the voltage at a rate of 0.1 V per second, that is, the driving voltage was measured and the external quantum efficiency at this time was measured.

[Table 2] Comparison of performance of devices manufactured using the compound of the present invention and the compound of the prior art as a hole transport material

Device example number compound number Voltage (V) EQE (%) light color Comparative Example 1 C1 5.4 5.5 deep blue light Comparative Example 2 C2 5.2 6.8 pale blue light Example 1 P1 4.7 6.9 deep blue light Example 2 P16 4.5 6.7 deep blue light Example 3 P29 4.9 6.2 deep blue light Example 4 P36 4.5 6.7 deep blue light Example 5 P44 4.3 6.9 deep blue light Example 6 P53 4.4 6.5 deep blue light Example 7 P54 4.8 6.5 deep blue light Example 8 P84 4.5 6.5 deep blue light Example 9 P96 4.7 6.6 deep blue light Example 10 P155 4.5 6.8 deep blue light Example 11 P159 4.5 6.6 deep blue light Example 12 P181 4.8 6.4 deep blue light Example 13 P182 4.6 6.6 deep blue light Example 14 P183 4.2 6.7 deep blue light Example 15 P184 4.5 6.3 deep blue light Example 16 P186 4.3 6.3 deep blue light Example 17 P187 4.9 6.4 deep blue light Example 18 P188 4.8 6.0 deep blue light Example 19 P189 5.0 6.2 deep blue light Example 20 P190 4.8 5.9 deep blue light Example 21 P191 4.9 6.0 deep blue light Example 22 P192 4.9 6.1 deep blue light

The above results show that, compared with the reference material C1, the B-N organic material of the present invention is used in an organic electroluminescent device, which has a stronger rigid structure and thus has a better carrier transport performance, resulting in a higher external quantum efficiency in an OLED device. It shows that it helps to indicate a voltage lower than and. Compared with the reference material C2, the B-N organic material of the present invention exhibits a bluer light color when used in an organic electroluminescent device. This is because C2 does not have a group represented by Formula (1) in the compound of the present invention, so it is assumed that when used in an organic electroluminescent device, only light blue light (470 nm to 490 nm) is emitted, but deep blue light cannot be obtained. In addition, compared to the reference material, the larger condensed rigid ring structure of the compound of the present invention is advantageous for near-planar arrangement of molecules, which is advantageous for light extraction, thereby improving external quantum efficiency.

P183을 사용한 실시예 14 ＞ P181을 사용한 실시예 12

P184를 사용한 실시예 15임을 알 수 있다. 이는 이미노기를 통해 특정 방향족기를 모핵에 연결하는 동시에 모핵과 상기 기 사이의 공액 구조를 끊어 얻어지는 본 발명의 일반식(1)의 화합물 때문일 수 있으며, 상기 화합물은 제1 일중항 발진기 강도가 상대적으로 높으므로 높은 외부 양자 효율을 나타낸다.The performance of the organic electroluminescent devices of Examples 12 to 15 is superior to Comparative Example 1, but slightly inferior to Example 1. Specifically, the light emitting layer dye of the organic electroluminescent device of Example 1 uses the compound P1 of the present invention, X ¹ and X ² are both NR ³ , while the compounds used in the organic electroluminescent devices of Examples 12 to 15 is P181 to P184, and X ¹ and X ² are CR ¹ R ² , O, S, and SiR ⁴ R ⁵ , respectively. From the above results, in terms of the external quantum efficiency of the device, Example 1 using P1 > Example 13 using P182

Example 14 with P183 > Example 12 with P181

It can be seen that this is Example 15 using P184. This may be due to the compound of the general formula (1) of the present invention obtained by linking a specific aromatic group to the parent nucleus through an imino group and at the same time breaking the conjugated structure between the parent nucleus and the group, and the compound has a first singlet oscillator strength relatively Therefore, it shows high external quantum efficiency.

Although the present invention has been described above with examples, the present invention is not limited to the above examples, and various modifications and improvements can be made by those skilled in the art within the scope of the present invention. However, it should be understood that the scope of the present invention is outlined through the appended claims.

Claims (13)

As an organic compound,
It has a structure represented by the following formula (1),

In Formula (1), X ¹ and X ² are each independently selected from CR ¹ R ² , NR ³ , O, S, or SiR ⁴ R ⁵ ;
When any one or plural of R ¹ to R ⁵ are present, they optionally form a ring together with ring A or ring D;
Ring A, ring D, and ring E are each independently one selected from a substituted or unsubstituted C5 to C30 aromatic ring and a substituted or unsubstituted C3 to C30 aromatic heterocyclic ring, at least one of which is represented by formula (a) has the structure, and the structure represented by formula (a) is condensed through ring F;
ring F and ring G are each independently selected from a substituted or unsubstituted C5 to C23 aromatic ring and a substituted or unsubstituted C3 to C23 aromatic heterocyclic ring;
Y ¹ and Y ² are each independently selected from CR ⁶ R ⁷ , NR ⁸ , O, S, or SiR ⁹ R ¹⁰ ;
R ¹ to R ¹⁰ are independently hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1 to C10 chain alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, substituted or unsubstituted C1 to one selected from C10 alkoxy, amino, substituted or unsubstituted C1 to C10 silyl, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C3 to C30 heteroaryl;
When a substituent is present in the above group, the substituent is halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C10 silyl, An organic compound characterized in that it is one or a combination of two or more selected from amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl. According to claim 1,
An organic compound, characterized in that X ¹ and X ² are each independently one selected from NR ³ , O, or S. According to claim 1,
At least one of X ¹ and X ² is NR ³ , R ³ is an organic compound, characterized in that one of a substituted or unsubstituted C6 ~ C30 aryl, a substituted or unsubstituted C3 ~ C30 heteroaryl. According to claim 1,
Y ¹ and Y ² are each independently selected from CR ⁶ R ⁷ , NR ⁸ , or O;
Preferably, at least one of Y ¹ and Y ² is CR ⁶ R ⁷ ;
More preferably, the organic compound characterized in that both Y ¹ and Y ² are CR ⁶ R ⁷ . According to claim 1,
R ⁶ and R ⁷ are each independently hydrogen, substituted or unsubstituted C1 ~ C10 chain alkyl, substituted or unsubstituted C3 ~ C10 cycloalkyl, substituted or unsubstituted C6 ~ C30 aryl, substituted or unsubstituted C3 is one selected from ~ C30 heteroaryl;
Preferably, R ⁶ and R ⁷ are each independently hydrogen or one selected from the following groups,

More preferably, the organic compound characterized in that both R ⁶ and R ⁷ are methyl. According to claim 1,
ring F is one selected from a substituted or unsubstituted C5-C14 aromatic ring and a substituted or unsubstituted C3-C14 aromatic hetero ring;
Preferably, ring F is one selected from a substituted or unsubstituted C5-C10 aromatic ring and a substituted or unsubstituted C3-C10 N-containing aromatic heterocyclic ring;
More preferably, ring F has a structure represented by the following formula (b),

In the above formula (b), * denotes a condensed site with the ring where the Y ¹ Y ² ring is located, and ring F is condensed with the parent nucleus through Z ¹ and Z ² , Z ² and Z ³ , or Z ³ and Z ⁴ and Z ¹ to Z ⁴ are each independently selected from C, CR ¹¹ , and N; R ¹¹ are each independently hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1 ~ C10 chain alkyl, substituted or unsubstituted C3 ~ C10 cycloalkyl, substituted or unsubstituted C1 ~ C10 Alkoxy, substituted or unsubstituted C1 ~ C10 silyl, amino, substituted or unsubstituted C6 ~ C30 arylamino, substituted or unsubstituted C3 ~ C30 heteroarylamino, substituted or unsubstituted C6 ~ C30 aryl, substituted or unsubstituted It is one selected from cyclic C3-C30 heteroaryl, wherein R ¹¹ is optionally linked to an adjacent aromatic ring or aromatic hetero ring to form a ring;
Even more preferably, Z ¹ to Z ⁴ are each independently CR ¹¹ , wherein each R ¹¹ is independently hydrogen or an organic compound, characterized in that one selected from the following groups.

According to claim 1,
Ring A, ring D, and ring E are each independently one selected from a substituted or unsubstituted C5-C14 aromatic ring and a substituted or unsubstituted C3-C14 aromatic hetero ring, at least one of which is represented by the above formula (a) has a structure that is;
Preferably, ring A and ring D are each independently selected from structures represented by formula (c) or formula (a) below, and ring E is represented by formula (c') or formula (a) below. structure, and at least one of ring A, ring D, and ring E has the structure represented by the formula (a),

In the above formula, * indicates a site connected to the parent nucleus, Z ⁵ ~ Z ⁸ , Z ^5' ~ Z ^7' are each independently selected from C, CR ¹¹ , and N; R ¹¹ are each independently hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1 ~ C10 chain alkyl, substituted or unsubstituted C3 ~ C10 cycloalkyl, substituted or unsubstituted C1 ~ C10 Alkoxy, substituted or unsubstituted C1 ~ C10 silyl, amino, substituted or unsubstituted C6 ~ C30 arylamino, substituted or unsubstituted C3 ~ C30 heteroarylamino, substituted or unsubstituted C6 ~ C30 aryl, substituted or unsubstituted It is one selected from cyclic C3-C30 heteroaryl, wherein R ¹¹ is optionally linked to an adjacent aromatic ring or aromatic hetero ring to form a ring;
More preferably, an organic compound characterized in that at least one of ring A and ring D has a structure represented by the formula (a). According to claim 7,
Z ⁵ to Z ⁸ are each independently CR ¹¹ , and each R ¹¹ is independently hydrogen or an organic compound, characterized in that one selected from the following groups.

According to claim 1,
ring G is one selected from a substituted or unsubstituted C5-C14 aromatic ring and a substituted or unsubstituted C3-C14 aromatic hetero ring;
Preferably, it is one selected from a substituted or unsubstituted C5 ~ C10 aromatic ring, a substituted or unsubstituted C3 ~ C10 N-containing aromatic heterocyclic ring;
More preferably, it is a structure represented by the following formula (b'),

In the above formula, * indicates a region condensed with a ring where the Y ¹ Y ² ring is located, and Z ^1' to Z ^4' are each independently selected from C, CR ¹² , and N; Wherein R ¹² is independently hydrogen, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1 ~ C10 chain alkyl, substituted or unsubstituted C3 ~ C10 cycloalkyl, substituted or unsubstituted C1 ~ C10 alkoxy , substituted or unsubstituted C1 ~ C10 silyl, amino, substituted or unsubstituted C6 ~ C30 arylamino, substituted or unsubstituted C3 ~ C30 heteroarylamino, substituted or unsubstituted C6 ~ C30 aryl, substituted or unsubstituted is one selected from C3 to C30 heteroaryl, wherein R ¹² is optionally condensed with a connected aromatic ring or aromatic hetero ring to form a ring. According to claim 1,
The organic compound characterized in that it has a structure represented by the following P1 to P192.

Application of the organic compound according to any one of claims 1 to 10 in an organic electroluminescent device. According to claim 11,
An application characterized in that it is applied as a light emitting layer material in an organic electroluminescent device. An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode,
An organic electroluminescent device characterized in that the organic layer contains the organic compound according to any one of claims 1 to 10.