JP2016505611A - Compound for organic optoelectronic device, organic light emitting device including the same, and display device including the organic light emitting device - Google Patents

Abstract

The present invention relates to a compound for an organic optoelectronic device, an organic light emitting device including the same, and a display device including the organic light emitting device, and provides a compound for an organic optoelectronic device represented by Chemical Formula 1.

Description

  The present invention relates to a compound for an organic optoelectronic device, an organic light emitting device including the compound, and a display device including the organic light emitting device.

  An organic optoelectronic device means a device that requires charge exchange between an electrode using holes or electrons and an organic substance.

  Organic optoelectronic devices are roughly classified into two types according to the principle of operation. First, excitons are formed in the organic material layer by photons flowing into the device from an external light source, and the excitons are separated into electrons and holes, which are transmitted to different electrodes, respectively. It is an electronic element of the form used as (voltage source). The second is an electronic device in which a voltage or current is applied to two or more electrodes to inject holes or electrons into an organic semiconductor that forms an interface with the electrodes, and the device operates by the injected electrons and holes.

  Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, organic photoreceptor drums, organic transistors, etc., all of which are used to inject or transport holes to drive the device. Requires an electron injection or transport material, or a luminescent material.

  In particular, organic light emitting devices (OLEDs) have recently attracted attention with increasing demand for flat panel displays. In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance.

  Such an organic light-emitting element is an element that converts electric energy into light by applying an electric current to an organic light-emitting material, and usually has a structure in which a functional organic material layer is inserted between an anode and a cathode. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer often has a multilayer structure composed of different materials, for example, a hole injection layer, a hole transport layer, a light emitting layer. , An electron transport layer, an electron injection layer, and the like.

  In such an organic light emitting device structure, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic material layer, and the injected holes and electrons meet to recombine. To form high-energy excitons. At this time, light having a specific wavelength is generated while the formed excitons move to the ground state again.

  Recently, it is known that not only fluorescent light-emitting substances but also phosphorescent light-emitting substances can be used as light-emitting substances for organic light-emitting devices. Such phosphorescence emission is caused by inter-system transition after electrons transition from the ground state to the excited state. This is performed by a mechanism in which singlet excitons undergo non-light-emission transition to triplet excitons due to crossing, and then triplet excitons emit light while transitioning to the ground state.

  As described above, in the organic light emitting device, the material used as the organic material layer is classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, and an electron injection material, depending on the function. it can.

  The light emitting materials are classified into blue, green and red light emitting materials and yellow and amber light emitting materials necessary for realizing a better natural color according to the light emission color.

  On the other hand, when only one substance is used as the light emitting material, the maximum emission wavelength shifts to a long wavelength due to intermolecular interaction, and problems such as a decrease in color purity and a decrease in device efficiency due to the light emission attenuation effect occur. A host / dopant system can be used as the luminescent material to increase the emission efficiency and stability due to energy transfer.

  In order for the organic light emitting device to fully exhibit the above-described excellent characteristics, a material forming an organic material layer in the device, for example, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, Among the light-emitting materials, it must be preceded that the host and / or dopant is assisted by a stable and efficient material, and the development of a stable and efficient organic material for organic light-emitting devices has been sufficiently developed. Therefore, the development of new materials continues to be required. The necessity for such material development is the same in the other organic optoelectronic devices described above.

  In addition, low-molecular organic light-emitting elements are manufactured in the form of a thin film by a vacuum deposition method, so that the efficiency and life performance are good. On the other hand, high-molecular organic light-emitting elements use an inkjet method or a spin coat method, so initial investment There is an advantage that the cost is small and it is advantageous for the large area.

  Both low-molecular organic light-emitting elements and high-molecular organic light-emitting elements have advantages such as self-emission, high-speed response, wide viewing angle, ultra-thinness, high image quality, durability, and wide driving temperature range. It is attracting attention as a display. In particular, it is a self-luminous type compared to existing liquid crystal displays (LCDs), has good visibility even in dark places or when external light enters, does not require a backlight, and is 1/3 level of LCD The thickness and weight can be reduced.

  In addition, since the response speed is in microsecond units, which is 1000 times faster than that of the LCD, it is possible to realize a perfect moving image with no afterimage. Therefore, recently, it is expected to attract attention as an optimal display in accordance with the full-fledged multimedia era. Based on such advantages, since it was first developed in the late 1980s, the efficiency has been increased by 80 times and the lifetime has been increased to 100. The rapid technological development has reached more than double, and recently, a 40-inch organic light-emitting element panel has been announced, and the size has been rapidly increasing.

  To increase the size, it is necessary to increase the light emission efficiency and improve the lifetime of the device. Therefore, it is necessary to develop a stable and efficient organic layer material for organic light emitting devices.

  Provided is a compound for an organic optoelectronic device capable of providing an organic optoelectronic device having characteristics such as high efficiency and long life.

  Provided are an organic light emitting device including the compound for organic optoelectronic devices and a display device including the organic light emitting device.

  In one embodiment of the present invention, a compound for an organic optoelectronic device represented by the following chemical formula 1 is provided.

In Formula 1, Ar ¹ is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a combination thereof, and L ^{1 to} L ³ are independent of each other. Substituted or unsubstituted C2-C6 alkenylene group, substituted or unsubstituted C2-C6 alkynylene group, substituted or unsubstituted C6-C30 arylene group, substituted or unsubstituted C2-C30 heteroarylene group, Or a combination thereof, n1 to n3 are each independently an integer of 0 to 3, A is the following chemical formula A-2, B is the following chemical formula A-2, A substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group:

In Formula A-2, X ¹ is —O— or —S—, and R ³ and R ⁴ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or Unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2- C30 heteroaryl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 C20 acyl group, substituted or unsubstituted C2-C20 alkoxycarbonyl group, substituted or unsubstituted C2-C2 Acyloxy group, substituted or unsubstituted C2-C20 acylamino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoylamino group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or An unsubstituted C1-C20 heterocyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

  The B may be the following A-2.

The Ar ¹ may be represented by the following chemical formula B-1.

In Formula B-1, R ^{5 to} R ⁸ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, A carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1- C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 Alkoxycarbonyl group, substituted or unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 acylamino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoylamino Group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 hetero A cyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

The Ar ¹ may be represented by the following chemical formula B-2.

In Formula B-2, R ^{5 to} R ⁸ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, A carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1- C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 Alkoxycarbonyl group, substituted or unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 acylamino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoylamino Group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 hetero A cyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

The Ar ¹ may be represented by the following chemical formula B-3.

In Formula B-3, R ^{9 to} R ¹² are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, A carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1- C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 An alkoxycarbonyl group, a substituted or unsubstituted C2-C20 acyloxy group, substituted or unsubstituted Substituted C2-C20 acylamino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoyl Amino group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkyl thiol group, substituted or unsubstituted C6-C20 aryl thiol group, substituted or unsubstituted C1-C20 A heterocyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

The Ar ¹ may be represented by the following chemical formula B-4.

The Ar ¹ may be represented by the following chemical formula B-5.

In Formula B-5, X ² is —O—, —S— or NR ′, and R ′, R ¹³ and R ¹⁴ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group. Amino group, substituted or unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted Or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted Or an unsubstituted C1-C20 acyl group, a substituted or unsubstituted C2-C20 alkoxycarbonyl group, a substituted or unsubstituted A substituted C2-C20 acyloxy group, a substituted or unsubstituted C2-C20 acylamino group, a substituted or unsubstituted C2-C20 alkoxycarbonylamino group, a substituted or unsubstituted C7-C20 aryloxycarbonylamino group, Substituted or unsubstituted C1-C20 sulfamoylamino group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 aryl A thiol group, a substituted or unsubstituted C1-C20 heterocyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

The Ar ¹ may be represented by the following chemical formula B-6.

In Formula B-6, R ¹⁵ and R ¹⁶ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, A carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1- C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 An alkoxycarbonyl group, a substituted or unsubstituted C2-C20 acyloxy group, substituted Is an unsubstituted C2-C20 acylamino group, a substituted or unsubstituted C2-C20 alkoxycarbonylamino group, a substituted or unsubstituted C7-C20 aryloxycarbonylamino group, a substituted or unsubstituted C1-C20 sulfo group. Famoylamino group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 A C20 heterocyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

Ar ¹ may be a substituted or unsubstituted biphenyl group.

  A and B may be a substituent represented by the chemical formula A-2.

In the chemical formula A-2, R ³ and R ⁴ may be hydrogen.

  The organic optoelectronic device compound may have a molecular weight of 700 or less.

  The organic optoelectronic device compound may have a molecular weight of 600 or less.

  The organic optoelectronic element may be any one selected from the group consisting of an organic photoelectric element, an organic light emitting element, an organic solar battery, an organic transistor, an organic photoreceptor drum, and an organic memory element.

  In another embodiment of the present invention, in an organic light emitting device including an anode, a cathode, and at least one organic thin film layer interposed between the anode and the cathode, at least one of the organic thin film layers. The layer provides an organic light emitting device comprising the compound for organic optoelectronic devices.

  The organic thin film layer is any one selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and combinations thereof. Also good.

  The compound for an organic optoelectronic device may be included in the light emitting layer.

  The compound for an organic optoelectronic device may be used as a phosphorescent or fluorescent host material in the light emitting layer.

  In still another embodiment of the present invention, a display device including the organic light emitting device is provided.

  The organic optoelectronic device containing the compound for organic optoelectronic device has excellent electrochemical and thermal stability, excellent life characteristics, and high luminous efficiency even at a low driving voltage.

It is sectional drawing which shows various embodiment with respect to the organic light emitting element which can be manufactured using the compound for organic optoelectronic devices concerning one Embodiment of this invention. It is sectional drawing which shows various embodiment with respect to the organic light emitting element which can be manufactured using the compound for organic optoelectronic devices concerning one Embodiment of this invention. It is sectional drawing which shows various embodiment with respect to the organic light emitting element which can be manufactured using the compound for organic optoelectronic devices concerning one Embodiment of this invention. It is sectional drawing which shows various embodiment with respect to the organic light emitting element which can be manufactured using the compound for organic optoelectronic devices concerning one Embodiment of this invention. It is sectional drawing which shows various embodiment with respect to the organic light emitting element which can be manufactured using the compound for organic optoelectronic devices concerning one Embodiment of this invention.

  Hereinafter, embodiments of the present invention will be described in detail. However, this is provided as an example, and the present invention is not limited thereby, and the present invention is defined only by the scope of the claims to be described later.

  In this specification, unless otherwise defined, “substituted” means that at least one hydrogen in the substituent or compound is deuterium, halogen group, hydroxy group, amino group, substituted or unsubstituted C1-C30. Amine group, nitro group, substituted or unsubstituted C3-C40 silyl group, C1-C30 alkyl group, C1-C10 alkylsilyl group, C3-C30 cycloalkyl group, C6-C30 aryl group, C1 It means being substituted with a C1-C10 trifluoroalkyl group such as a C20 alkoxy group, a fluoro group, a trifluoromethyl group, or a cyano group.

  The substituted halogen group, hydroxy group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, substituted or unsubstituted C3-C40 silyl group, C1-C30 alkyl group, C1 C1-C10 alkylsilyl group, C3-C30 cycloalkyl group, C6-C30 aryl group, C1-C20 alkoxy group, C1-C10 trifluoroalkyl group such as fluoro group, trifluoromethyl group, or cyano group Two adjacent substituents may be fused to form a ring.

  In the present specification, unless otherwise defined, “hetero” contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P in one functional group, and the rest Means what is carbon.

  In the present specification, “a combination thereof” means that two or more substituents are bonded to a linking group or two or more substituents are condensed and bonded unless otherwise defined. To do.

  In the present specification, the “alkyl group” means an aliphatic hydrocarbon group unless otherwise defined. The alkyl group may be a “saturated alkyl group” that does not contain any double bond or triple bond.

  The alkyl group may be a C1-C20 alkyl group. More specifically, the alkyl group may be a C1-C10 alkyl group or a C1-C6 alkyl group. For example, a C1-C4 alkyl group means one having 1-4 carbon atoms in the alkyl chain, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and t-butyl. Those selected from the group consisting of

  Specific examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, A cyclohexyl group or the like is meant.

  “Aryl group” means a substituent in which all elements of a cyclic substituent have a p orbital, and these p orbitals form a conjugation, and are monocyclic or fused ring polycyclic ( That is, it includes a ring) functional group that separates adjacent pairs of carbon atoms.

  “Heteroaryl group” means an aryl group containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, and P, with the remainder being carbon. When the heteroaryl group is a fused ring, 1 to 3 heteroatoms may be included in each ring.

  In this specification, the hole characteristic means a characteristic that has a conductive characteristic by the HOMO level and facilitates injection of holes formed at the anode into the light emitting layer and movement in the light emitting layer. More specifically, it is similar to the characteristic of pushing out electrons.

  Further, the electronic property means a property that has a conductive property according to the LUMO level and facilitates injection of electrons formed in the cathode into the light emitting layer and movement in the light emitting layer. More specifically, it is similar to the property of attracting electrons.

  According to one embodiment of the present invention, a compound for an organic optoelectronic device represented by the following chemical formula 1 can be provided.

In Formula 1, Ar ¹ is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a combination thereof, and L ^{1 to} L ³ are independent of each other. Substituted or unsubstituted C2-C6 alkenylene group, substituted or unsubstituted C2-C6 alkynylene group, substituted or unsubstituted C6-C30 arylene group, substituted or unsubstituted C2-C30 heteroarylene group, Or a combination thereof, n1 to n3 are each independently an integer of 0 to 3, A is the following chemical formula A-2, B is the following chemical formula A-2, A substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group.

In Formula A-2, X ¹ is —O— or —S—, and R ^{1 to} R ⁴ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or Unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2- C30 heteroaryl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 C20 acyl group, substituted or unsubstituted C2 to C20 alkoxycarbonyl group, substituted or unsubstituted C2 to C20 An acyloxy group, a substituted or unsubstituted C2-C20 acylamino group, a substituted or unsubstituted C2-C20 alkoxycarbonylamino group, a substituted or unsubstituted C7-C20 aryloxycarbonylamino group, a substituted or unsubstituted C1 -C20 sulfamoylamino group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or non-substituted A substituted C1-C20 heterocyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

The compound represented by Formula 1 may have an amine group including a substituent including an indeno structure as a core structure. In the case of such a core structure, a substituent capable of exhibiting hole characteristics in the structure of Ar ¹ is combined with the amine group core, whereby a structure in which electrons or holes easily flow can be provided. In addition, since the substituent having an indeno structure has a structure having an unshared electron pair, the flow of electrons or holes is improved, the molecular weight is small, and the substituent is suitable as an evaporation material. Generally, in the case of a material for vapor deposition, if the molecular weight exceeds 1000, a problem of thermal stability may be induced. The structure substituted with Ar ¹ is characterized by having abundant electrons (electron donors rich in π bonds), and the substituent of the indeno structure is an electron of Ar ¹ through an amine. The structure in which the compound is attracted can prevent the uneven distribution of electrons in the compound. As a result, high efficiency and long life of the device can be achieved.

  In addition, the compound for an organic optoelectronic device represented by the chemical formula 1 is a compound having various energy band gaps by introducing various other substituents into the core portion and the substituents substituted in the core portion. It may be.

  By using a compound having an appropriate energy level in accordance with the substituent of the compound in the organic optoelectronic device, the hole transfer capability or the electron transfer capability is enhanced, and has an excellent effect in terms of efficiency and driving voltage. In addition, it has excellent electrochemical and thermal stability, and can improve the life characteristics during driving of the organic optoelectronic device.

  More specifically, in one embodiment of the present invention, a substituted or unsubstituted C6-C30 aryl group and / or a substituted or unsubstituted C2-C30 heteroaryl group is a substituted or unsubstituted phenyl group. Substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenylyl group, substituted Or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted perylenyl group, substituted or unsubstituted Indenyl group, substituted or unsubstituted furanyl group, substituted or Unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted Thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl Group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted Isoki Linyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted It may be, but is not limited to, a substituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, or a combination thereof.

Moreover, by selectively adjusting the L ^{1 to} L ³ , the conjugate length of the entire compound can be determined, and thereby the triplet energy band gap can be adjusted. Thereby, the characteristic of the material required for an organic optoelectronic device is realizable. The triplet energy band gap can also be adjusted by changing the bonding positions of ortho, para, and meta.

Specific examples of L ^{1 to} L ³ include a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, substituted or unsubstituted Anthracenylene group, substituted or unsubstituted phenanthrylene group, substituted or unsubstituted pyrenylene group, substituted or unsubstituted fluorenylene group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted Or an unsubstituted perylenyl group.

More specifically, the L ^{1 to} L ³ may be independently a phenylene group. When L ^{1 to} L ³ are phenylene groups, the core portions on both sides based on the phenylene group may be bonded to ortho, meta, or para.

The B may be represented by the following chemical formula A-2. Since the chemical formula A-2 has an unshared electron pair, it is advantageous for improving the flow of electrons or holes and obtaining a highly efficient device. Moreover, since molecular weight is small compared with the dibenzofuran or dibenzothiophene generally used, it can be advantageous as a vapor deposition material. Then, a highly efficient / long-life device can be obtained by uniformly distributing the electrons (π bond, electron donating group) unevenly distributed in Ar ¹ throughout the compound with the substituent of Chemical Formula A-2. it can. More specifically, when the compound for an organic optoelectronic device includes two indeno structures, electrons can be uniformly distributed.

More specifically, the Ar ¹ may be represented by the following chemical formula B-1.

In Formula B-1, R ^{5 to} R ⁸ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, A carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1- C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 Alkoxycarbonyl group, substituted or unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 acylamino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoylamino Group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 hetero A cyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

  In this case, in the case of a fluorene group as represented by the chemical formula B-1, the π bond is interrupted because the central carbon (C) is formed without a double bond. For this reason, it becomes easy to form a hole, and it can make | form with the substitution body of the indeno structure centering on amine (N). In order to transmit electrons or holes satisfactorily, a substituent that easily forms holes and a substituent that easily forms electrons must be well harmonized, but the fluorene group forms holes. It is an easy substitute. In the case of a compound containing fluorene, the characteristics can be improved in terms of the high efficiency of the device and the driving voltage.

As a specific example, the Ar ¹ may be represented by the following chemical formula B-2.

In Formula B-2, R ^{5 to} R ⁸ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, A carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1- C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 Alkoxycarbonyl group, substituted or unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 acylamino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoylamino Group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 hetero A cyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

  The substituent represented by the chemical formula B-2 can be bonded to the core amine nitrogen at a position where synthesis is easy.

More specifically, the Ar ¹ may be represented by the following chemical formula B-3.

In Formula B-3, R ^{9 to} R ¹² are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, A carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1- C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 An alkoxycarbonyl group, a substituted or unsubstituted C2-C20 acyloxy group, substituted or unsubstituted Substituted C2-C20 acylamino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoyl Amino group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkyl thiol group, substituted or unsubstituted C6-C20 aryl thiol group, substituted or unsubstituted C1-C20 A heterocyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

  When a phenanthrene group as shown in Formula B-3 is present, a lower HOMO level can be achieved. The phenanthrene (B-2) group is known as a structure that easily forms holes because three phenyl groups are broken. And compared with a fluorene (B-1) group, it is excellent in thermal stability (all phenyl groups make a resonance structure).

More specifically, the Ar ¹ may be represented by the following chemical formula B-4.

  More specifically, when a HOMO level lower than that of the phenanthrene (Chemical Formula B-2) group is required, a triphenylene (Chemical Formula B-3) group can be introduced and adjusted. The triphenylene group has three phenyl groups, can provide abundant electron donating groups, and has a structure that easily forms holes when combined with an electron withdrawing group (for example, an indeno substituent). obtain. And it is excellent in thermal stability (all of the phenyl groups have a resonance structure) compared to the fluorene group.

More specifically, the Ar ¹ may be represented by the following chemical formula B-5.

In Formula B-5, X ² is —O—, —S— or NR ′, and R ′, R ¹³ and R ¹⁴ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group. Amino group, substituted or unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted Or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted Or an unsubstituted C1-C20 acyl group, a substituted or unsubstituted C2-C20 alkoxycarbonyl group, a substituted or unsubstituted A substituted C2-C20 acyloxy group, a substituted or unsubstituted C2-C20 acylamino group, a substituted or unsubstituted C2-C20 alkoxycarbonylamino group, a substituted or unsubstituted C7-C20 aryloxycarbonylamino group, Substituted or unsubstituted C1-C20 sulfamoylamino group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 aryl A thiol group, a substituted or unsubstituted C1-C20 heterocyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

  When the chemical formula B-5, which is excellent in hole or electron transport capability, is used, a highly efficient device can be obtained.

More specifically, the Ar ¹ may be represented by the following chemical formula B-6.

In Formula B-6, R ¹⁵ and R ¹⁶ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, A carboxyl group, a ferrocenyl group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1- C20 alkoxy group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 An alkoxycarbonyl group, a substituted or unsubstituted C2-C20 acyloxy group, substituted Is an unsubstituted C2-C20 acylamino group, a substituted or unsubstituted C2-C20 alkoxycarbonylamino group, a substituted or unsubstituted C7-C20 aryloxycarbonylamino group, a substituted or unsubstituted C1-C20 sulfo group. Famoylamino group, substituted or unsubstituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 A C20 heterocyclothiol group, a substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.

  In the case of the carbazole group represented by the chemical formula B-6, the π bond is interrupted around the amine (N), which is advantageous for forming holes, and since it has an unshared electron pair, Excellent transport capability. In addition, since the carbazole group as represented by the chemical formula B-6 has a hole transporting capability that is very superior to the electron transporting capability, a hole transporting layer or an auxiliary layer of the hole transporting layer can be applied to the device. Alternatively, when used as a host having hole characteristics, a high-efficiency low-voltage element can be realized.

More specifically, Ar ¹ may be a substituted or unsubstituted biphenyl group. As a more specific example, Ar ¹ may be represented by the following chemical formula B-7 or B-8.

  The substituent of B-7 and / or B-8 having a simpler structure is excellent in thermal and electrical stability and is suitable for realizing a device having a long lifetime.

  As a specific example, the A and B may be represented by the chemical formula A-2. That is, when the substituent represented by the chemical formula A-2 is simultaneously present in the amine group of the core, the presence of the chemical formula A-2 excellent in hole or electron transport reduces the driving voltage of the device, and improves the efficiency. It can be improved. Further, the chemical formula A-2 has a simple molecular structure, and thus has excellent thermal and electrical stability.

In the chemical formula A-2, R ³ and R ⁴ may be hydrogen, but are not limited thereto.

  The organic optoelectronic device compound may have a molecular weight of 700 or less. More specifically, it can have a molecular weight of 600 or less. In this case, since vapor deposition can be performed at a low temperature when the device is manufactured, vapor deposition is easy, and thermal stability can be improved. Thereby, the stability of the element can be improved.

  Specific examples of one embodiment of the present invention include the following compounds. However, it is not necessarily limited to these.

  In another embodiment of the present invention, an anode, a cathode, and one or more organic thin film layers interposed between the anode and the cathode, wherein at least one of the organic thin film layers is the organic photoelectron. An organic optoelectronic device comprising a device compound is provided.

  The compound for an organic optoelectronic device is used in an organic thin film layer, and can improve the life characteristics, efficiency characteristics, electrochemical stability and thermal stability of the organic optoelectronic device, and reduce the driving voltage.

  Specifically, the organic thin film layer may be a light emitting layer.

  The organic optoelectronic device may be an organic light emitting device, an organic photoelectric device, an organic solar cell, an organic transistor, an organic photoreceptor drum, or an organic memory device.

  More specifically, the organic optoelectronic device may be an organic light emitting device. 1-5 is sectional drawing of the organic light emitting element containing the compound for organic optoelectronic devices based on one Embodiment of this invention.

  1 to 5, an organic light emitting device 100, 200, 300, 400 and 500 according to an embodiment of the present invention includes an anode 120, a cathode 110, and at least interposed between the anode and the cathode. It has a structure including one organic thin film layer 105.

The anode 120 includes an anode material, and the anode material is preferably a material having a large work function so that hole injection into the organic thin film layer is usually smooth. Specific examples of anode materials include metals such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), Examples include metal oxides such as indium zinc oxide (IZO), and combinations of metals and oxides such as ZnO and Al, or SnO ₂ and Sb, and include poly (3-methylthiophene) and poly ( Examples include, but are not limited to, conductive polymers such as 3,4- (ethylene-1,2-dioxy) thiophene: PEDT), polypyrrole, and polyaniline. More specifically, a transparent electrode containing ITO can be used as the anode.

The cathode 110 includes a cathode material, and the cathode material is preferably a material having a small work function so that the electron injection into the organic thin film layer is facilitated. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, and alloys thereof. , LiF / Al, LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca, but not limited to these. More specifically, a metal electrode such as aluminum can be used as the cathode.

  Referring to FIG. 1, FIG. 1 shows an organic light emitting device 100 in which only the light emitting layer 130 exists as the organic thin film layer 105, and the organic thin film layer 105 exists only in the light emitting layer 130. Also good.

  Referring to FIG. 2, FIG. 2 shows a two-layer organic light emitting device 200 in which a light emitting layer 230 including an electron transport layer and a hole transport layer 140 are present as the organic thin film layer 105. As described above, the organic thin film layer 105 may be a two-layer type including the light emitting layer 230 and the hole transport layer 140. In this case, the light emitting layer 130 functions as an electron transport layer, and the hole transport layer 140 functions to improve the bonding property with a transparent electrode such as ITO and the hole transport property.

  Referring to FIG. 3, FIG. 3 illustrates a three-layer organic light emitting device 300 in which an electron transport layer 150, a light emitting layer 130, and a hole transport layer 140 are present as the organic thin film layer 105. 105, the light emitting layer 130 has an independent form, and shows a form in which films having excellent electron transportability and hole transportability (electron transport layer 150 and hole transport layer 140) are stacked as separate layers. Yes.

  Referring to FIG. 4, FIG. 4 illustrates a four-layer organic light emitting device 400 in which an electron injection layer 160, a light emitting layer 130, a hole transport layer 140, and a hole injection layer 170 are present as the organic thin film layer 105. In addition, the hole injection layer 170 can improve the bonding property with ITO used as an anode.

  Referring to FIG. 5, the organic thin film layer 105 has different functions such as an electron injection layer 160, an electron transport layer 150, a light emitting layer 130, a hole transport layer 140, and a hole injection layer 170. A five-layer organic light emitting device 500 having five layers is shown. The organic light emitting device 500 is formed with an electron injection layer 160 separately, which is effective for lowering the voltage.

  1 to 5, the group consisting of the electron transport layer 150, the electron injection layer 160, the light emitting layers 130 and 230, the hole transport layer 140, the hole injection layer 170, and combinations thereof forming the organic thin film layer 105. Any one selected from the above includes the material for an organic optoelectronic device.

  The compound for an organic optoelectronic device can be used for the light emitting layers 130 and 230. At this time, it can be used as a green phosphorescent material in the light emitting layer.

  More specifically, the compound for an organic optoelectronic device can be used for the hole transport layer. Although not shown, a plurality of hole transport layers may exist. When the hole transport layer adjacent to the light emitting layer is viewed as an auxiliary layer, the compound for an organic optoelectronic device is formed in the auxiliary layer. May be present.

  The organic light emitting device described above is formed by forming a positive electrode on a substrate, and then forming a dry film formation method such as vacuum deposition, sputtering, plasma plating and ion plating; or spin coating, dipping, fluid coating, etc. After the organic thin film layer is formed by a wet film forming method or the like, the cathode can be formed on the organic thin film layer.

  In yet another embodiment of the present invention, a display device including the organic optoelectronic device is provided.

  Hereinafter, specific examples of the present invention will be presented. However, the examples described below are only for specifically illustrating or explaining the present invention, and the present invention is not limited thereby.

(Manufacture of compounds for organic optoelectronic devices)
Synthesis Example 1 Production of Intermediate I-1

1-Bromo-4-chlorobenzene (53.7 g, 280.7 mmol) was dissolved in 0.5 L of tetrahydrofuran (THF) under a nitrogen atmosphere, and then benzofuran-2-boronic acid (50.0 g, 308.7 mmol). ) And tetrakis (triphenylphosphine) palladium (16.2 g, 14.0 mmol) were added and stirred. Saturated potassium carbonate (82.7 g, 561.4 mmol) was added to water, and the mixture was heated to reflux at 100 ° C. for 47 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound I-1 (50.8 g, 79%).

  HRMS (70 eV, EI +): m / z calcd for C14H9ClO: 228.0342, found: 228. Elemental Analysis: C, 74%; H, 4%.

Synthesis Example 2: Production of Intermediate I-2

In a nitrogen atmosphere, 1-bromo-4-chlorobenzene (48.9 g, 255.3 mmol) was dissolved in 0.5 L of tetrahydrofuran (THF), and then benzothiophene-2-boronic acid (50.0 g, 280. 9 mmol) and tetrakis (triphenylphosphine) palladium (8.85 g, 7.66 mmol) were added and stirred. Saturated potassium carbonate (75.2 g, 510.6 mmol) was added to water, and the mixture was heated to reflux at 80 ° C. for 17 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound I-2 (61.3 g, 98%).

  HRMS (70 eV, EI +): m / z calcd for C14H9ClS: 224.0113, found: 224. Elemental Analysis: C, 69%; H, 4%.

Synthesis Example 3 Production of Intermediate I-3

1-Bromo-4-nitrobenzene (50 g, 247.5 mmol) was dissolved in 0.5 L of tetrahydrofuran (THF) in a nitrogen atmosphere, and then 9,9-dimethyl-9H-fluoren-2-ylboronic acid (70 0.7 g, 297.0 mmol) and tetrakis (triphenylphosphine) palladium (8.58 g, 7.43 mmol) were added and stirred. Saturated potassium carbonate (72.9 g, 495.0 mmol) was added to water, and the mixture was heated to reflux at 80 ° C. for 21 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound I-3 (78.1 g, 82%).

  HRMS (70 eV, EI +): m / z calcd for C21H17NO2: 315.1259, found: 315. Elemental Analysis: C, 80%; H, 5%.

Synthesis Example 4: Production of Intermediate I-4

I-3 (30 g, 95.1 mmol) was dissolved in 0.3 L of dm tetrahydrofuran (THF) under a nitrogen atmosphere, 0.3 L of methanol was added, and the mixture was cooled to 0 ° C. To this was added sodium borohydride (36.0 g, 951 mmol), tin (II) chloride (90.2 g, 475.5 mmol) was added, and the mixture was reacted at room temperature for 2 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (EA). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain I-4 (14.9 g, 55%).

  HRMS (70 eV, EI +): m / z calcd for C21H19N: 285.1517, found: 285. Elemental Analysis: C, 88%; H, 7%.

Synthesis Example 5 Production of Intermediate I-5

In a nitrogen atmosphere, 1-bromo-4-nitrobenzene (50 g, 247.5 mmol) was dissolved in 0.6 L of tetrahydrofuran (THF), and then dibenzofuran-4-ylboronic acid (63.0 g, 297.0 mmol) and Tetrakis (triphenylphosphine) palladium (8.58 g, 7.43 mmol) was added and stirred. Saturated potassium carbonate (72.9 g, 495.0 mmol) was added to water, and the mixture was heated to reflux at 80 ° C. for 24 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound I-5 (53.7 g, 75%).

  HRMS (70 eV, EI +): m / z calcd for C18H11NO3: 289.0739, found: 289. Elemental Analysis: C, 75%; H, 4%.

Synthesis Example 6 Production of Intermediate I-6

Under a nitrogen atmosphere, I-5 (30 g, 103.7 mmol) was dissolved in 0.3 L of dm tetrahydrofuran (THF), 0.3 L of methanol was added, and the mixture was cooled to 0 ° C. To this was added sodium borohydride (39.2 g, 1,037 mmol), and then tin (II) chloride (98.3 g, 518.5 mmol) was added, followed by reaction at room temperature for 3 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (EA). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 1-6 (14.0 g, 52%).

  HRMS (70 eV, EI +): m / z calcd for C18H13NO: 259.0997, found: 259. Elemental Analysis: C, 83%; H, 5%.

Synthesis Example 7 Production of Intermediate I-7

Under a nitrogen atmosphere, carbazole (50 g, 299.0 mmol) was dissolved in 0.5 L of toluene, and this was added to 1-bromo-4-nitrobenzene (60.4 g, 299.0 mmol), tris (diphenylideneacetone) Palladium (0) (8.24 g, 8.97 mmol), tris-tert-butylphosphine (7.26 g, 35.9 mmol), and sodium tert-butoxide (34.5 g, 358.8 mmol) were sequentially added at 130 ° C. And heated at reflux for 46 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound I-7 (74.1 g, 86%).

  HRMS (70 eV, EI +): m / z calcd for C18H12N2O2: 288.0899, found: 288. Elemental Analysis: C, 75%; H, 4%.

Synthesis Example 8 Production of Intermediate I-8

Under a nitrogen atmosphere, I-7 (30 g, 104.1 mmol) was dissolved in 0.3 L of dm tetrahydrofuran (THF), 0.3 L of methanol was added, and the mixture was cooled to 0 ° C. To this was added sodium borohydride (39.4 g, 1,041 mmol), and then tin (II) chloride (98.7 g, 520.5 mmol) was added, followed by reaction at room temperature for 3 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (EA). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain 1-6 (11.6 g, 43%).

  HRMS (70 eV, EI +): m / z calcd for C18H14N2: 258.1157, found: 258. Elemental Analysis: C, 84%; H, 5%.

Example 1 Preparation of Compound 2

Under a nitrogen atmosphere, 9,9-dimethyl-9H-fluoren-2-amine (15.5 g, 74.1 mmol) was dissolved in 0.35 L of toluene, and then this was mixed with intermediate I-1 (50.8 g, 222 .2 mmol), tris (diphenylideneacetone) dipalladium (0) (2.0 g, 2.22 mmol), tris-tert-butylphosphine (1.80 g, 4.23 mmol), and sodium tert-butoxide (15. 7 g, 162.9 mmol) was sequentially added, and the mixture was heated to reflux at 100 ° C. for 3 days. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 1 (37.4 g, 85%).

  HRMS (70 eV, EI +): m / z calcd for C43H31NO2: 593.2355, found: 593. Elemental Analysis: C, 87%; H, 5%.

Example 2: Preparation of compound 3

Under a nitrogen atmosphere, 9,9-dimethyl-9H-fluoren-2-amine (19.4 g, 92.9 mmol) was dissolved in 0.35 L of toluene, and then intermediate I-2 (50 g, 204.3 mmol) was dissolved therein. ), Tris (diphenylideneacetone) dipalladium (0) (2.55 g, 2.79 mmol), tris-tert-butylphosphine (2.26 g, 11.1 mmol), and sodium tert-butoxide (19.6 g, 204.4 mmol) was sequentially added, and the mixture was heated to reflux at 100 ° C for 25 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound 3 (54.0 g, 93%).

  HRMS (70 eV, EI +): m / z calcd for C43H31NS2: 615.1898, found: 625. Elemental Analysis: C, 83%; H, 5%.

Example 3: Preparation of compound 4

Under a nitrogen atmosphere, intermediate I-4 (10 g, 35.0 mmol) was dissolved in 0.15 L of toluene, and this was mixed with intermediate I-2 (18.9 g, 77.1 mmol), tris (diphenylideneacetone). ) Dipalladium (0) (0.96 g, 1.05 mmol), tris-tert-butylphosphine (0.85 g, 4.2 mmol), and sodium tert-butoxide (7.41 g, 77.1 mmol) were added sequentially, The mixture was heated to reflux at 100 ° C. for 22 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound 5 (20.9 g, 85%).

  HRMS (70 eV, EI +): m / z calcd for C49H35NS2: 701.2211, found: 701. Elemental Analysis: C, 84%; H, 5%.

Example 4: Preparation of compound 110

Under a nitrogen atmosphere, N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (10 g, 27.7 mmol) was dissolved in 0.1 L of toluene, and then intermediate I -1 (13.9 g, 60.9 mmol), tris (diphenylideneacetone) dipalladium (0) (0.76 g, 0.83 mmol), tris-tert-butylphosphine (0.67 g, 3.32 mmol), And sodium tert-butoxide (5.85 g, 60.9 mmol) were sequentially added, and the mixture was heated to reflux at 100 ° C. for 13 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 110 (13.9 g, 91%).

  HRMS (70 eV, EI +): m / z calcd for C41H31NO: 5533.2406, found: 553. Elemental Analysis: C, 89%; H, 6%.

Example 5: Preparation of compound 129

4- (9-Phenyl-9H-carbazol-3-yl) aniline (10 g, 29.9 mmol) was dissolved in 0.1 L of toluene under a nitrogen atmosphere, and then intermediate I-2 (16.1 g, 65.8 mmol), tris (diphenylideneacetone) dipalladium (0) (0.82 g, 0.90 mmol), tris-tert-butylphosphine (0.73 g, 3.59 mmol), and sodium tert-butoxide (6 .32 g, 65.8 mmol) was sequentially added, and the mixture was heated to reflux at 100 ° C. for 17 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 129 (19.8 g, 88%).

  HRMS (70 eV, EI +): m / z calcd for C52H34N2S2: 750.2163, found: 750. Elemental Analysis: C, 83%; H, 5%.

Example 6: Preparation of compound 141

Under a nitrogen atmosphere, phenanthren-2-amine (10 g, 51.7 mmol) was dissolved in 0.15 L of toluene, and then this was mixed with intermediate I-2 (27.9 g, 113.8 mmol), tris (diphenylideneacetone). ) Dipalladium (0) (1.42 g, 1.55 mmol), tris-tert-butylphosphine (1.26 g, 6.2 mmol), and sodium tert-butoxide (10.9 g, 113.8 mmol) were added sequentially, The mixture was heated to reflux at 100 ° C. for 23 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 141 (30.9 g, 98%).

  HRMS (70 eV, EI +): m / z calcd for C42H27NS2: 609.1585, found: 609. Elemental Analysis: C, 83%; H, 4%.

Example 7: Preparation of compound 150

Triphenylene-2-amine (10 g, 41.1 mmol) was dissolved in 0.16 L of toluene under a nitrogen atmosphere, and then intermediate I-2 (22.1 g, 90.4 mmol), tris (diphenylideneacetone) were added thereto. ) Dipalladium (0) (1.13 g, 1.23 mmol), tris-tert-butylphosphine (1.0 g, 4.93 mmol), and sodium tert-butoxide (8.69 g, 90.4 mmol) were added sequentially, The mixture was heated to reflux at 100 ° C. for 21 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 150 (25.2 g, 93%).

  HRMS (70 eV, EI +): m / z calcd for C46H29NS2: 6599.1742, found: 659. Elemental Analysis: C, 84%; H, 4%.

Example 8: Preparation of compound 153

In a nitrogen atmosphere, biphenyl-4-amine (10 g, 59.1 mmol) was dissolved in 0.16 L of toluene, and then this was mixed with intermediate I-2 (31.8 g, 130.0 mmol), tris (diphenylideneacetone). ) Dipalladium (0) (1.62 g, 1.77 mmol), tris-tert-butylphosphine (1.43 g, 7.09 mmol), and sodium tert-butoxide (12.5 g, 130.0 mmol) were added sequentially, The mixture was heated to reflux at 100 ° C. for 14 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 153 (33.2 g, 96%).

  HRMS (70 eV, EI +): m / z calcd for C40H27NS2: 5855.1585, found: 585. Elemental Analysis: C, 82%; H, 5%.

Example 9: Preparation of compound 159

Under a nitrogen atmosphere, intermediate I-6 (10 g, 38.6 mmol) was dissolved in 0.15 L of toluene, and then intermediate I-2 (20.8 g, 84.8 mmol), tris (diphenylideneacetone) ) Dipalladium (0) (1.06 g, 1.16 mmol), tris-tert-butylphosphine (0.94 g, 4.63 mmol), and sodium tert-butoxide (8.15 g, 84.8 mmol) were added sequentially, The mixture was heated to reflux at 100 ° C. for 16 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 159 (22.2 g, 96%).

  HRMS (70 eV, EI +): m / z calcd for C46H29NOS2: 675.1691, found: 675. Elemental Analysis: C, 82%; H, 4%.

Example 10: Preparation of compound 171

Under a nitrogen atmosphere, Intermediate I-8 (10 g, 38.7 mmol) was dissolved in 0.16 L of toluene, and then this was mixed with Intermediate I-2 (20.8 g, 85.2 mmol), Tris (diphenylideneacetone). ) Dipalladium (0) (1.06 g, 1.16 mmol), tris-tert-butylphosphine (0.94 g, 4.64 mmol), and sodium tert-butoxide (8.19 g, 85.2 mmol) were added sequentially, The mixture was heated to reflux at 100 ° C. for 18 hours. After completion of the reaction, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM). Water was removed with anhydrous MgSO ₄ , filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain Compound 171 (23.5 g, 90%).

  HRMS (70 eV, EI +): m / z calcd for C46H30N2S2: 674.1850, found: 674. Elemental Analysis: C, 82%; H, 4%.

(Manufacture of organic light emitting devices)
Example 11: Production of an organic light emitting device (blue common layer)
A glass substrate coated with a thin film of indium tin oxide (ITO) with a thickness of 1500 mm was cleaned with distilled water ultrasonic waves. After cleaning, the substrate was ultrasonically cleaned with a solvent such as isopropanol, acetone, methanol, etc., dried, transferred to a plasma cleaner, the substrate was cleaned with oxygen plasma for 5 minutes, and the substrate was transferred to a vacuum deposition machine. Using the ITO transparent electrode thus prepared as an anode, 4,4′-bis (N- [4- {N, N′-bis (3-methylphenyl) amino} -phenyl is formed on the top of the ITO substrate. ] -N-phenylamino) biphenyl (DNTPD) was vacuum deposited to form a hole injection layer having a thickness of 600 mm. Next, using the compound 2 produced in Example 1, a hole transport layer having a thickness of 300 mm was formed by vacuum deposition. On the hole transport layer, 9,10-di- (2-naphthyl) anthracene (AND) is used as a host, and 2,5,8,11-tetra (tert-butyl) perylene (TBPe) is used as a dopant. A light-emitting layer having a thickness of 250 mm was formed by doping with 3% by weight and vacuum deposition. Thereafter, Alq3 was vacuum deposited on the light emitting layer to form an electron transport layer having a thickness of 250 mm. An organic light emitting device was manufactured by sequentially vacuum depositing 10% LiF and 1000% Al on the electron transport layer to form a cathode.

  The organic light emitting device has a structure having five organic thin film layers, specifically, Al (1000 Å) / LiF (10 Å) / Alq3 (250 Å) / EML [AND: TBPe = 97: 3]. It was produced with a structure of (250Å) / HTL (300Å) / DNTPD (600Å) / ITO (1500Å).

Example 12
In Example 11, an organic light emitting device was manufactured in the same manner except that Example 2 was used instead of Example 1.

Example 13
An organic light emitting device was manufactured in the same manner as in Example 11 except that Example 3 was used instead of Example 1.

Example 14
In Example 11, an organic light emitting device was manufactured in the same manner except that Example 4 was used instead of Example 1.

Example 15
In Example 11, an organic light emitting device was manufactured in the same manner except that Example 5 was used instead of Example 1.

Example 16
An organic light emitting device was manufactured in the same manner as in Example 11 except that Example 6 was used instead of Example 1.

Example 17
An organic light emitting device was manufactured in the same manner as in Example 11 except that Example 7 was used instead of Example 1.

Example 18
In Example 11, an organic light emitting device was manufactured in the same manner except that Example 8 was used instead of Example 1.

Example 19
In Example 11, an organic light emitting device was manufactured in the same manner except that Example 9 was used instead of Example 1.

Example 20
In Example 11, an organic light emitting device was manufactured in the same manner except that Example 10 was used instead of Example 1.

Comparative Example 1
In Example 11, an organic light emitting device was manufactured in the same manner except that NPB was used instead of Example 1. The structure of the NPB is described below.

Comparative Example 2
An organic light emitting device was manufactured in the same manner as in Example 11 except that HT1 was used instead of Example 1. The structure of HT1 is described below.

Comparative Example 3
An organic light emitting device was manufactured in the same manner as in Example 11 except that HT2 was used instead of Example 1. The structure of HT2 is described below.

  The structures of DNTPD, AND, TBPe, NPB, HT1, and HT2 used for manufacturing the organic light emitting device are as follows.

(Measurement of organic light emitting device performance)
For each of the organic light emitting devices manufactured in Examples 11 to 20 and Comparative Examples 1 to 3, a change in current density, a change in luminance, and luminous efficiency in accordance with voltage were measured. The specific measurement method is as follows, and the results are shown in Table 1 below.

(1) Measurement of change in current density according to change in voltage Current flowing through the unit element using a current-voltmeter (Keithley 2400) while increasing the voltage from 0 V to 10 V with respect to the manufactured organic light emitting element The value was measured and the measured current value was divided by the area to obtain the result.

(2) Measurement of luminance change according to voltage change While increasing the voltage from 0V to 10V on the manufactured organic light emitting device, the luminance at that time was measured using a luminance meter (Minolta Cs-1000A). And got the result.

(3) Measurement of luminous efficiency Using the luminance, current density and voltage measured from (1) and (2) above, the current efficiency (cd / A) of the same current density (10 mA / cm ² ) was calculated. .

  According to the result of the said Table 1, in the case of Examples 11-14 in which the fluorene substituent is contained, it turns out that efficiency improves significantly compared with Comparative Examples 1-2. In the case of the comparative example 3, it has a fluorene substituent, and since efficiency is the highest among the comparative examples, it can be seen that the fluorene substituent significantly improves the efficiency. In the case of Examples 11-20, it turns out that a drive voltage is low compared with Comparative Examples 1-3 as a whole. From this, it can be inferred that the indeno substituent reduces the drive voltage. In Example 18 in which the simplest structure is used, the half-life is the highest, so it can be seen that the basic structure contributes to the lifetime of the device to some extent. Based on this, a low voltage, high efficiency, high brightness, long life organic light emitting device having excellent hole injection and hole transfer capability could be produced.

  The present invention is not limited to the above-described embodiments, and can be manufactured in various forms different from each other. Those having ordinary knowledge in the technical field to which the present invention pertains It can be understood that the present invention can be implemented in other specific forms without changing essential characteristics. Therefore, it should be understood that the embodiments described above are illustrative in all aspects and not limiting.

DESCRIPTION OF SYMBOLS 100: Organic light emitting element 110: Cathode 120: Anode 105: Organic thin film layer 130: Light emitting layer 140: Hole transport layer 150: Electron transport layer 160: Electron injection layer 170: Hole injection layer 230: Light emitting layer + electron transport layer

Claims (19)

Compound for organic optoelectronic device represented by chemical formula 1 below:
In Formula 1,
Ar ¹ is a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, or a combination thereof;
L ^{1 to} L ³ each independently represent a substituted or unsubstituted C 2 to C 6 alkenylene group, a substituted or unsubstituted C 2 to C 6 alkynylene group, a substituted or unsubstituted C 6 to C 30 arylene group, substituted or unsubstituted A substituted C2-C30 heteroarylene group, or a combination thereof,
n1 to n3 are each independently an integer of 0 to 3,
A is the following chemical formula A-2,
B is the following Formula A-2, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heteroaryl group:
In the chemical formula A-2,
X ¹ is —O— or —S—;
R ³ and R ⁴ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted Or an unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, substituted or Unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 alkoxycarbonyl group, substituted or Unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 acyl Amino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoylamino group, substituted or non-substituted Substituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 heterocyclothiol group, substituted Alternatively, it is an unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof.   The said B is a compound for organic optoelectronic devices of Claim 1 which is following Chemical formula A-2. The compound for organic optoelectronic devices according to claim 1, wherein Ar ¹ is represented by the following chemical formula B-1.
In the chemical formula B-1,
R ^{5 to} R ⁸ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted Or an unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, substituted or Unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 alkoxycarbonyl group, substituted or Unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 acyloxy group Group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted Substituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 heterocyclothiol group, substituted Alternatively, it is an unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof. The compound for organic optoelectronic devices according to claim 1, wherein Ar ¹ is represented by the following chemical formula B-2:
In the chemical formula B-2,
R ^{5 to} R ⁸ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted Or an unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, substituted or Unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 alkoxycarbonyl group, substituted or Unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 acyloxy group Group, substituted or unsubstituted C2 to C20 alkoxycarbonylamino group, substituted or unsubstituted C7 to C20 aryloxycarbonylamino group, substituted or unsubstituted C1 to C20 sulfamoylamino group, substituted or unsubstituted Substituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 heterocyclothiol group, substituted Alternatively, it is an unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof. The compound for organic optoelectronic device according to claim 1, wherein Ar ¹ is represented by the following chemical formula B-3:
In the chemical formula B-3,
R ^{9 to} R ¹² are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted Or an unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, substituted or Unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 alkoxycarbonyl group, substituted or Unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 acyl Mino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoylamino group, substituted or non-substituted Substituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 heterocyclothiol group, substituted Alternatively, it is an unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof. The compound for organic optoelectronic devices according to claim 1, wherein Ar ¹ is represented by the following chemical formula B-4.
The compound for organic optoelectronic device according to claim 1, wherein Ar ¹ is represented by the following chemical formula B-5:
In the chemical formula B-5,
X ² is —O—, —S— or NR ′;
R ¹³ , R ¹⁴ and R ′ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, carboxyl group, Ferrocenyl group, substituted or unsubstituted C1-C20 alkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, substituted or unsubstituted C1-C20 alkoxy Group, substituted or unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 alkoxycarbonyl Group, substituted or unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2- 20 acylamino groups, substituted or unsubstituted C2-C20 alkoxycarbonylamino groups, substituted or unsubstituted C7-C20 aryloxycarbonylamino groups, substituted or unsubstituted C1-C20 sulfamoylamino groups, substituted Or an unsubstituted C1-C20 sulfonyl group, a substituted or unsubstituted C1-C20 alkylthiol group, a substituted or unsubstituted C6-C20 arylthiol group, a substituted or unsubstituted C1-C20 heterocyclothiol group A substituted or unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof. The compound for organic optoelectronic device according to claim 1, wherein Ar ¹ is represented by the following chemical formula B-6:
In the chemical formula B-6,
R ¹⁵ and R ¹⁶ are independently of each other hydrogen, deuterium, halogen group, cyano group, hydroxyl group, amino group, substituted or unsubstituted C1-C20 amine group, nitro group, carboxyl group, ferrocenyl group, substituted Or an unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C20 alkoxy group, substituted or Unsubstituted C6-C20 aryloxy group, substituted or unsubstituted C3-C40 silyloxy group, substituted or unsubstituted C1-C20 acyl group, substituted or unsubstituted C2-C20 alkoxycarbonyl group, substituted or Unsubstituted C2-C20 acyloxy group, substituted or unsubstituted C2-C20 Silamino group, substituted or unsubstituted C2-C20 alkoxycarbonylamino group, substituted or unsubstituted C7-C20 aryloxycarbonylamino group, substituted or unsubstituted C1-C20 sulfamoylamino group, substituted or non-substituted Substituted C1-C20 sulfonyl group, substituted or unsubstituted C1-C20 alkylthiol group, substituted or unsubstituted C6-C20 arylthiol group, substituted or unsubstituted C1-C20 heterocyclothiol group, substituted Alternatively, it is an unsubstituted C1-C20 ureido group, a substituted or unsubstituted C3-C40 silyl group, or a combination thereof. The compound for organic optoelectronic device according to claim 1, wherein Ar ¹ is a substituted or unsubstituted biphenyl group.   The compound for organic optoelectronic devices according to claim 1, wherein A and B are substituents represented by the chemical formula A-2. 2. The compound for an organic optoelectronic device according to claim 1, wherein in the chemical formula A-2, R ³ and R ⁴ are hydrogen.   The compound for organic optoelectronic devices according to claim 1, wherein the compound for organic optoelectronic devices has a molecular weight of 700 or less.   The said compound for organic optoelectronic devices is a compound for organic optoelectronic devices of Claim 1 which has a molecular weight of 600 or less.   2. The organic optoelectronic device according to claim 1, wherein the organic optoelectronic device is any one selected from the group consisting of an organic photoelectric device, an organic light emitting device, an organic solar cell, an organic transistor, an organic photoreceptor drum, and an organic memory device. Compounds for organic optoelectronic devices. In an organic light emitting device comprising an anode, a cathode, and at least one organic thin film layer interposed between the anode and the cathode,
At least any one layer of the said organic thin film layer is an organic light emitting element containing the compound for organic optoelectronic devices of the said Claim 1.   The organic thin film layer is any one selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and combinations thereof. The organic light emitting device according to claim 15.   The organic light emitting device according to claim 16, wherein the compound for an organic optoelectronic device is contained in a light emitting layer.   The organic light-emitting device according to claim 17, wherein the compound for an organic optoelectronic device is used as a phosphorescent or fluorescent host material in a light-emitting layer.   The display apparatus containing the organic light emitting element of Claim 15.