WO2023195828A1 - Organic compound and organic light-emitting device comprising same - Google Patents

Abstract

The present invention relates to: an organic compound which can improve the color reproductivity, driving voltage, efficiency, and lifetime characteristics of an organic light-emitting device and can exhibit excellent color reproductivity and color purity in a blue light-emitting layer; and an organic light-emitting device comprising same.

Description

Organic compounds and organic light-emitting devices containing them

The present invention relates to organic compounds and organic light-emitting devices containing the same.

Organic light emitting devices (OLEDs) have a simple structure compared to other flat panel display devices such as existing liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), have various advantages in the manufacturing process, and have high Due to its excellent brightness and viewing angle characteristics, fast response speed, and low driving voltage, it has been actively developed and commercialized to be used as a light source for flat displays such as wall-mounted TVs, backlight of displays, lighting, and billboards. there is.

Organic light-emitting devices were first reported by C. W. Tang of Eastman Kodak (C. W. Tang, S. A. Vanslyke, Applied Physics Letters, Volume 51, Page 913, 1987), and their light-emitting principle is generally that when a voltage is applied, Holes injected from the anode and electrons injected from the cathode recombine to form an exciton, an electron-hole pair, and the energy of this exciton is converted into light by transferring it to a light-emitting material.

An organic light emitting device has a structure including a cathode (electron injection electrode), an anode (hole injection electrode), and one or more organic layers disposed between the two electrodes. At this time, the organic light emitting device consists of a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), or an electron transport layer (ETL) from the anode. It is laminated in the order of the injection layer (EIL), and to increase the efficiency of the light-emitting layer, a hole transport auxiliary layer or a hole blocking layer (HBL) may be additionally included in contact with the light-emitting layer.

The light-emitting layer is composed of two materials, a host and a dopant. The dopant must have high quantum efficiency, and the host material has a larger energy gap than the dopant material to facilitate energy transfer to the dopant. It is advisable to choose

The light-emitting layer can be broadly classified into blue, green, and red depending on the color it emits. The materials used as existing blue dopants are mostly fluorescent molecules such as perylene, coumarine, anthracene, and pyrene, but the dopant's emission spectrum half width (full width) Because the width half the maximum is approximately 40nm, there is a limitation that it is difficult to implement deep blue. In addition, there is a problem that optical loss occurs even when a certain wavelength section is amplified through optical resonance in a front light emitting device.

To solve this problem, boron-based dopants with a narrow device emission spectrum and high device efficiency have recently emerged. However, despite high efficiency and excellent color implementation, higher lifetime performance is required due to low lifetime. Accordingly, there is still a need to develop a dopant material that can satisfy the excellent color rendering and efficiency of boron-based dopants and improve its lifespan at the same time.

The present invention provides an organic compound that can improve the driving voltage, efficiency, and lifespan characteristics of an organic light-emitting device and exhibit excellent color rendering, and an organic light-emitting device applied to the organic light-emitting layer.

The present invention is not limited to the purposes mentioned above, and other purposes and advantages of the present invention that are not mentioned can be understood by the following description and will be more clearly understood by the examples of the present invention. In addition, it will be readily apparent that the objects and advantages of the present invention can be realized by the means and combinations thereof indicated in the patent claims.

In order to solve the above problems, according to one aspect of the present invention, an organic compound having a novel structure represented by the following Chemical Formula 1 can be provided, and the definition of the following Chemical Formula 1 is the same as that described in the specification and claims.

<Formula 1>

According to another aspect of the present invention, a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer may include a light-emitting layer, and may provide an organic light-emitting device containing the organic compound represented by Formula 1 of the present invention. You can.

By applying the organic compound represented by Formula 1 of the present invention to the dopant of the light-emitting layer of the organic light-emitting device, the driving voltage, efficiency, and lifespan characteristics of the organic light-emitting device can be improved, and in particular, the blue light-emitting layer can exhibit excellent color representation and color purity. there is.

The effects of the present specification are not limited to the effects mentioned above, and other effects not mentioned will be clearly understood by those skilled in the art from the description below.

The above-described objects, features, and advantages will be described in detail below, and accordingly, those skilled in the art will be able to easily implement the technical idea of the present invention.

In describing the present specification, if it is determined that a detailed description of related known technology may unnecessarily obscure the gist of the present specification, the detailed description will be omitted.

In this specification, when “includes,” “has,” “consists of,” “arranges,” “provides,” etc. are used as constituent elements, other parts may be added unless “only” is used. When a component is expressed in the singular, the plural is included unless specifically stated otherwise.

In interpreting the components in this specification, they are interpreted to include the margin of error even if there is no separate explicit description.

In this specification, the “top (or bottom)” of a component or the arrangement of any component on the “top (or bottom)” of a component means that any component is disposed in contact with the top (or bottom) of the component. In addition, it may mean that other components may be interposed between the component and any component disposed on (or under) the component.

As used herein, the term “halo” or “halogen” includes fluorine, chlorine, bromine and iodine.

As used herein, the term “alkyl group” refers to both straight-chain alkyl radicals and branched-chain alkyl radicals. Unless otherwise specified, the alkyl group contains 1 to 30 carbon atoms and includes methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, etc., and the alkyl group may be optionally substituted.

As used herein, the term “cycloalkyl group” refers to a cyclic alkyl radical. Unless otherwise specified, the cycloalkyl group contains 3 to 20 carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, etc., and the cycloalkyl group may be optionally substituted.

As used herein, the term “alkenyl group” refers to both straight-chain alkene radicals and branched-chain alkene radicals. Unless otherwise specified, the alkenyl group contains 2 to 30 carbon atoms, and the alkenyl group may be optionally substituted.

As used herein, the term “cycloalkenyl group” refers to a cyclic alkenyl radical. Unless there is a specific limitation, the cycloalkenyl group contains 3 to 20 carbon atoms, and the cycloalkenyl group may be optionally substituted.

As used herein, the term “alkynyl group” refers to both straight-chain alkyne radicals and branched-chain alkyne radicals. Unless otherwise specified, an alkynyl group contains 2 to 30 carbon atoms. Additionally, the alkynyl group may be optionally substituted.

As used herein, the term “cycloalkynyl group” refers to a cyclic alkynyl radical. Unless there is a specific limitation, the cycloalkynyl group contains 3 to 20 carbon atoms, and in addition, the cycloalkynyl group may be optionally substituted.

The terms “aralkyl group” or “arylalkyl group” used herein are used interchangeably and mean an alkyl group having an aromatic group as a substituent. Additionally, the aralkyl group (arylalkyl group) may be optionally substituted.

As used herein, the terms “aryl group” or “aromatic group” are used with the same meaning, and the aryl group includes both single ring groups and polycyclic ring groups. Polycyclic rings may include “condensed rings,” which are two or more rings in which two carbons are common to two adjacent rings. Unless there is a specific limitation, the aryl group contains 6 to 30 carbon atoms, and in addition, the aryl group may be optionally substituted.

As used herein, the term "heterocyclic group" means that at least one of the carbon atoms constituting the aryl group, cycloalkyl group, cycloalkenyl group, cycloalkynyl group, aralkyl group (arylalkyl group), arylamino group, etc. is oxygen (O). , means substituted with a heteroatom such as nitrogen (N), sulfur (S), etc., and with reference to the above definition, heteroaryl group, heterocycloalkyl group, heterocycloalkenyl group, heterocycloalkynyl group, heteroatom It includes an alkyl group (heteroarylalkyl group), heteroarylamino group, etc. Additionally, the heterocycle may be optionally substituted.

As used herein, unless otherwise specified, the term "carbon ring" refers to an alicyclic ring group such as "cycloalkyl group", "cycloalkenyl group", "cycloalkynyl group" and an aromatic ring group "aryl group (aromatic group). )" can be used as a term that includes both.

As used herein, the terms "heteroalkyl group", "heteroalkenyl group", "heteroalkynyl group", and "heteroaralkyl group (heteroarylalkyl group)" mean that at least one of the carbon atoms constituting the group is oxygen (O) or nitrogen. It means substitution with heteroatoms such as (N) and sulfur (S). Additionally, heteroalkyl group, heteroalkenyl group, heteroalkynyl group, and heteroaralkyl group (heteroarylalkyl group) may be optionally substituted.

As used herein, the terms “alkylamino group”, “aralkyl amino group”, “arylamino group”, and “heteroarylamino group” refer to an alkyl group, aralkyl group, aryl group, or heteroaryl group, which is a hetero ring, in which an amine group is substituted. , means including both secondary and tertiary amines, and in addition, alkylamino group, aralkylamino group, arylamino group, and heteroarylamino group may be optionally substituted.

As used herein, the terms “alkylsilyl group”, “arylsilyl group”, “alkoxy group”, “aryloxy group”, “alkylthio group”, and “arylthio group” refer to the alkyl group and the aryl group, respectively. It means that the group and thio group are substituted, and in addition, the alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylthio group, and arylthio group may be arbitrarily substituted.

The term “substituted” used herein means that a substituent other than hydrogen (H) is bonded to the corresponding carbon, and when there are multiple substituents, each substituent may be the same or different from each other.

Unless specifically limited in the present specification, the position to be substituted is not limited as long as it is a position where a hydrogen atom is substituted, that is, a position where a substituent can be substituted. If two or more substituents exist, the substituents may be the same or different from each other. there is.

Each object and substituent defined in this specification may be the same or different, unless otherwise specified.

Hereinafter, the organic compound according to the present invention and the organic light-emitting device containing the same will be described in detail.

Compared to existing boron-based dopant materials, the organic compound represented by Formula 1 of the present invention contains an acridine condensed ring derivative at the central boron (corresponding to Y in Formula 1 of the present invention) and a 5-membered (5 -membered) or 6-membered ring structure (corresponding to the A member and B member in Chemical Formula 1 of the present invention) is connected.

In this way, the _acridine condensed ring structure containing the substituent of When applied, it can show the advantage of improving the characteristics of the device, such as increasing its lifespan.

Additionally, the A and B members, which are 5-membered or 6-membered ring structures of Formula 1 of the present invention, are selected as aryl groups or heteroaryl groups, thereby improving device efficiency. In particular, in the case of a heteroaryl group, an additional shoulder peak was generated in the graph analyzed according to Photoluminescence Spectroscopy (PL), which increases the overall graph area and increases the overall device efficiency. It was confirmed that was superior.

In this way, when the dopant material of the light-emitting layer of the organic light-emitting device includes an organic compound represented by the following formula (1), the luminous efficiency and lifespan of the organic light-emitting device can be increased, the driving voltage can be lowered, and excellent color reproduction and color purity can be exhibited. The possible effects were experimentally confirmed and the present invention was completed.

<Formula 1>

In Formula 1, Y may be any one of boron (B), nitrogen (N), P=O, and P=S.

X ₁ may be any one of nitrogen (N), P=O and P=S, and X ₁ is a substituent included in the acridine condensed structure derivative. X ₂ may be one selected from the group consisting of oxygen (O), sulfur (S), N (R ₇ ), C (R ₈ ) (R ₉ ), and Si (R ₈ ) (R ₉ ).

n may be an integer from 0 to 2.

m, p, and q may each independently be an integer from 0 to 4. However, as defined below, the A and B members may each be selected as a 5-membered ring or a 6-membered ring, and accordingly, the upper limits of p and q may be 3 or 4.

The A member and the B member may be the same or different from each other, and may each independently be selected from the group consisting of Formulas 2 to 6, which have a 5-membered ring or 6-membered ring structure as follows.

<Formula 2>

<Formula 3>

<Formula 4>

<Formula 5>

<Formula 6>

In Formulas ₂ to 6 _, * represents _{a position} bonded to Y, It may be one selected from the group consisting of N(R ₇ ), C(R ₈ )(R ₉ ), and Si(R ₈ )(R ₉ ).

R ₁ to R ₉ may be the same or different from each other, and each independently represents hydrogen, deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, trimethylsilylethynyl group (TMS), substituted or unsubstituted. an alkyl group with 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, a substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group with 3 to 20 carbon atoms, substituted or Unsubstituted alkynyl group with 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group with 3 to 20 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, Substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted heteroaralkyl group having 3 to 30 carbon atoms, substituted or unsubstituted amine group, substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted Or an unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 3 to 30 carbon atoms, a substituted or unsubstituted silyl group, substituted or Unsubstituted alkylsilyl group with 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl group with 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group with 1 to 30 carbon atoms, substituted or unsubstituted aryl with 6 to 30 carbon atoms It may be one selected from an oxy group, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.

Optionally, two adjacent groups among R ₁ to R ₉ may be combined (condensed) with each other to form a carbon ring structure, and the carbon ring structure may be a cycloalkyl group, an aryl group, a heteroaryl group, or a combination thereof. It could be one. In addition, two adjacent groups among R ₁ to R ₉ are combined with each other to form a carbon ring structure, which means that when a substituent is present on each of R ₁ to R ₉ , the substituents also participate in forming a carbon ring structure. It can be included.

In addition, when R ₁ , R ₄ , R ₅ and R ₆ each exist in plural, two adjacent groups may combine to form a carbon ring structure. For example, when n is 2 or more, two adjacent R _1s may be combined to form a ring structure. For example, when m is 2 or more, two adjacent R _4s may form a ring structure. For example, when p is 2 or more, two adjacent R _5s can be combined to form a carbon ring structure. For example, when q is 2 or more, two adjacent R _6s can be combined to form a carbon ring structure.

Optionally, when each of R ₁ to R ₉ is substituted, the substituents are each independently deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, trimethylsilylethynyl group (TMS), and carbon number 1. Alkyl group with 3 to 30 carbon atoms, cycloalkyl group with 3 to 20 carbon atoms, alkenyl group with 2 to 30 carbon atoms, cycloalkenyl group with 3 to 20 carbon atoms, alkynyl group with 2 to 30 carbon atoms, cycloalkenyl group with 3 to 20 carbon atoms, 6 to 6 carbon atoms Aryl group of 30, aralkyl group of 7 to 30 carbon atoms, heteroaryl group of 3 to 30 carbon atoms, heteroaralkyl group of 3 to 30 carbon atoms, amine group, alkylamino group of 1 to 30 carbon atoms, aralkylamino group of 7 to 30 carbon atoms , arylamino group with 6 to 30 carbon atoms, heteroarylamino group with 3 to 30 carbon atoms, silyl group, alkylsilyl group with 1 to 30 carbon atoms, arylsilyl group with 6 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, 6 to 6 carbon atoms. It may be one or more selected from the group consisting of an aryloxy group having 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms. When there are multiple substituents, the substituents may be the same or different from each other.

According to one embodiment of the present invention, X ₃ and X ₄ may be the same or different from each other, and are each independently selected from the group consisting of oxygen (O), sulfur (S), and N (R ₇ ). You can.

According to one embodiment of the present invention, R ₁ to R ₉ may be the same or different from each other, and each independently represents hydrogen, deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, trimethylsilyl ethyl group. Nyl group (TMS), substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 10 carbon atoms, substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, substituted or unsubstituted carbon number of 3 Cycloalkenyl group with 10 to 10 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 20 carbon atoms, substituted or unsubstituted cycloalkenyl group with 3 to 10 carbon atoms, substituted or unsubstituted aryl group with 6 to 20 carbon atoms, substituted or unsubstituted Aralkyl group having 7 to 20 carbon atoms in the ring, substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, substituted or unsubstituted heteroaralkyl group having 3 to 20 carbon atoms, substituted or unsubstituted amine group, substituted or unsubstituted Alkylamino group with 1 to 20 carbon atoms, substituted or unsubstituted aralkylamino group with 7 to 20 carbon atoms, substituted or unsubstituted arylamino group with 6 to 20 carbon atoms, substituted or unsubstituted heteroarylamino group with 3 to 20 carbon atoms, substituted Or an unsubstituted silyl group, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or It may be one selected from an unsubstituted aryloxy group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, R ₁ to R ₉ may be the same or different from each other, and each independently represents hydrogen, deuterium, a substituted or unsubstituted methyl group, or a substituted or unsubstituted ethyl group. group), substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted terbutyl group, substituted or unsubstituted isobutyl group group), substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthalenyl group, substituted or unsubstituted phenanthrenyl group group), substituted or unsubstituted fluorene group, substituted or unsubstituted spirofluorene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted Dibenzothiophene group, substituted or unsubstituted furan group, substituted or unsubstituted thiophene group, substituted or unsubstituted carbazole group, substituted or unsubstituted Substituted diphenylamine group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyrimidine group, substituted or unsubstituted piperidine group and substituted Or it may be one selected from the group consisting of an unsubstituted acridine group.

According to one embodiment of the present invention, R ₂ and R ₃ may be the same as or different from each other, and each independently. For example, it may be a substituted or unsubstituted methyl group, but is not limited thereto.

According to one embodiment of the present invention, Formula 1 is a structure in which both A and B members are selected as Formula 6, and can be represented by Formula 7 below.

<Formula 7>

According to one embodiment of the present invention, Formula 1 is a structure in which one of the A and B members is selected from Formula 2 to Formula 5, and the remaining of the A and B members are selected from Formula 6, and has the following Formula 8: It may be represented by one selected from the group consisting of Formula 11.

<Formula 8>

<Formula 9>

<Formula 10>

<Formula 11>

According to one embodiment of the present invention, Formula 1 is a structure in which both the A and B members are selected from one of Formulas 2 to 5, and may be represented by one selected from the group consisting of Formulas 12 to 15 below.

<Formula 12>

<Formula 13>

<Formula 14>

<Formula 15>

Each definition of Formula 7 to Formula 15 is the same as defined in Formula 1.

According to one embodiment of the present invention, in Formulas 12 to 15, X ₃ and X ₄ are the same as or different from each other, and may each independently be either oxygen (O) or sulfur (S).

According _{to one} embodiment of the present _invention , A group consisting of a cycloalkyl group of 3 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group of 3 to 30 carbon atoms, or a substituted or unsubstituted heteroarylalkyl group of 3 to 30 carbon atoms. It can be one selected from .

According to one embodiment of the present invention, R ₁ is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 to 20 carbon atoms. Aryl group of 30, substituted or unsubstituted heteroaryl group of 3 to 60 carbon atoms, substituted or unsubstituted alkylamino group of 1 to 30 carbon atoms, substituted or unsubstituted arylamino group of 6 to 30 carbon atoms, substituted or unsubstituted It may be one selected from the group consisting of an aralkylamino group having 7 to 30 carbon atoms and a substituted or unsubstituted heteroarylamino group having 3 to 30 carbon atoms.

According to one embodiment of the present invention, R ₂ and R ₃ are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, It may be one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 63 carbon atoms.

According to one embodiment of the present invention, the compound represented by Formula 1 is: It may be one selected from the group consisting of Compound 1 to Compound 286 below, but is not limited thereto as long as it falls within the definition of Formula 1.

.

According to one embodiment of the present invention, a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode. The organic layer may include a light-emitting layer, and the light-emitting layer may include an organic compound represented by Formula 1.

According to one embodiment of the present invention, the light-emitting layer may be a blue light-emitting layer, and the organic compound may be used as a blue dopant of the light-emitting layer.

According to one embodiment of the present invention, the PL wavelength of the blue emission layer may be, for example, 400 nm to 600 nm, for example, 430 nm to 480 nm, or for example, 445 nm to 460 nm.

According to one embodiment of the present invention, the light-emitting layer may be formed by doping the organic compound represented by Formula 1 as a dopant that emits blue light in order to improve the light-emitting efficiency of the host and the device.

According to one embodiment of the present invention, the doping concentration of the dopant can be adjusted within the range of 1 to 30% by weight based on the total weight of the host, but is not limited thereto, for example, the doping concentration is 2 to 20% by weight. % by weight, for example 3 to 15 % by weight, for example 5 to 10 % by weight, for example 3 to 8 % by weight, for example 2 to 7 % by weight. It can be.

According to one embodiment of the present invention, the CIEx and CIEy coordinate systems, which are the color coordinates of the blue light-emitting layer, are not particularly limited as long as they correspond to the blue light-emitting layer, but for example, CIEx may be 0.10 to 0.15, and CIEy may be 0.03 to 0.10. You can.

According to one embodiment of the present invention, the organic layer includes a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron suppression layer, a light emission auxiliary layer, a charge generation layer, a hole suppression layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. It may further include one or more selected from the group consisting of layers.

According to one embodiment of the present invention, the organic layer disposed between the first electrode and the second electrode sequentially includes a hole injection layer (HIL), a hole transfer layer (HTL), Hole transfer auxiliary layer, electron blocking layer, emission auxiliary layer, charge generation layer, hole blocking layer, electron transport auxiliary The structure may include an electron transfer auxiliary layer (electron transfer auxiliary layer), an emission material layer (EML), an electron transfer layer (ETL), and an electron injection layer (EIL). A second electrode may be formed on the electron injection layer, and optionally, a capping layer (CPL) and/or a protective layer (encapsulation layer) may be formed on the second electrode.

According to one embodiment of the present invention, the organic light emitting device includes a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; Devices for flexible lighting, either monochromatic or white; Vehicle display devices; and a display device for virtual or augmented reality.

Hereinafter, synthesis examples and examples of the present invention will be described. However, the following example is only an example of the present invention and is not limited thereto.

Synthesis example

<Equation 1>

According to Formula 1 above, the organic compound (“Product”) represented by Formula 1 of the present invention can be synthesized, and the specific synthesis method is as follows, but is not necessarily limited thereto.

Add 20.0 mmol (1eq) of Reactant and 10 volumes of t-butylbenzene to a 500 mL flask under nitrogen (N ₂ ) conditions, then slowly add 40.0 mmol (2eq) of t-Butyllithium at -78°C and incubate for 1 hour at room temperature and at 70°C. Stir for 2 hours. After confirming that all the reactant has disappeared using thin layer chromatography, add 40 mmol (2eq) of BBr ₃ at -78°C and stir for 1 hour at room temperature and 2 hours at 70°C. After confirming that the reaction was complete using thin layer chromatography, 40.0 mmol (2eq) of DIPEA was added and stirred at room temperature for 2 hours, then water was added, and the organic layer was extracted using dichloromethane. The extracted organic layer was filtered, concentrated, and purified using silica gel column chromatography to remove residual moisture using MgSO ₄ . Afterwards, it was recrystallized using a mixed solvent of dichloromethane and acetone to obtain the product as shown in Table 1 below.

[Table 1]

Example: Manufacturing of organic light emitting device

<Example 1>

The substrate on which ITO (100 nm), the anode of the organic light emitting device, was stacked was patterned by dividing it into a cathode, anode area, and insulating layer through an exposure (Photo-Lithograph) process, and then the work function of the anode (ITO) was calculated. For the purpose of increasing work-function and cleaning, the surface was treated with UV Ozone treatment and O ₂ :N ₂ plasma. On top of this, HAT-CN was formed to a thickness of 10 nm as a hole injection layer (HIL). Then, on top of the hole injection layer, N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4, as a hole transport layer, Vacuum deposition of 4'-diamine (N4,N4,N4',N4'-Tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) It is formed to a thickness of 90 nm, and N-phenyl-N-(4-(spiro[benzo[d,e]anthracene-7,9'-fluorene) is used as an electron blocking layer (EBL) on top of the hole transport layer (HTL). ]-2'-yl)phenyl)dibenzo[b,d]furan-4-amine (N-Phenyl-N-(4-(spiro[benzo[d, e]anthracene-7,9'-fluorene]- 2'-yl)phenyl)dibenzo[b,d]furan-4-amine) was formed to a thickness of 15 nm. 9-(1-Naphtyl)-10-(2-naphthyl)anthracene (9-(1-Naphtyl)-10-(2-Naphtyl)anthracene) was placed on the electron blocking layer (EBL) as a host for the light emitting layer. At the same time as deposition, 2 wt% of Compound 1 was doped as a dopant to form an emission layer (EML) with a thickness of 25 nm. On top of this, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (2- (4-(9,10-Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole) and LiQ were mixed at a weight ratio of 1:1 to form 25 nm An electron injection layer of 1 nm was deposited on the electron transport layer, and aluminum was deposited to a thickness of 100 nm as a cathode. Afterwards, a seal cap containing an adsorbent (getter) is bonded to the cathode using a UV curable adhesive to form a protective layer or encapsulation layer that can protect the organic light emitting device from oxygen or moisture in the atmosphere. An organic light emitting device was manufactured.

<Examples 2 to 31>

Organic light-emitting devices of Examples 2 to 31 were manufactured using the same method as Example 1, except that the compounds in Table 2 below were used as dopants instead of Compound 1.

<Comparative example>

An organic light-emitting device of Comparative Example was manufactured using the same method as Example 1, except that the following Comparative Example compound was used as a dopant instead of Compound 1.

⊙ Comparative example compound:

Experimental example: Characteristic analysis of organic light emitting devices

The organic light-emitting devices manufactured in Examples 1 to 31 and Comparative Examples were measured for electroluminescence characteristics, driving voltage and efficiency by applying a current of 10 mA/cm ² , and the T95 lifespan measured by constant current driving of 10 mA/cm ² was measured. Measurements were made and the values of the CIE coordinate system (x, y) were confirmed, and the results are compared and shown in Table 2 below.

[Table 2]

When the example compounds of the present invention were used as dopant materials for organic light-emitting devices, compared to the comparative examples, the driving voltage was low, efficiency was excellent, long lifespan was exhibited, and color was improved. It was confirmed that the recall rate was also excellent.

Although the embodiments of the present specification have been described in more detail above, the present specification is not necessarily limited to these embodiments, and various modifications may be made without departing from the technical spirit of the present specification. Accordingly, the embodiments disclosed in this specification are not intended to limit the technical idea of the present specification, but rather to explain it, and the scope of the technical idea of the present specification is not limited by these embodiments. Therefore, the embodiments described above should be understood in all respects as illustrative and not restrictive.

Claims (12)

1. Organic compound represented by the following formula (1):

   <Formula 1>

   

   In Formula 1,

   Y is any one of boron (B), nitrogen (N), P=O and P=S,

   X ₁ is any one of nitrogen (N), P=O and P=S,

   X ₂ is selected from the group consisting of oxygen (O), sulfur (S), N (R ₇ ), C (R ₈ ) (R ₉ ) and Si (R ₈ ) (R ₉ ),

   n is an integer from 0 to 2,

   m, p and q are each independently integers from 0 to 4,

   The A member and the B member are each independently selected from the group consisting of Formulas 2 to 6 below,

   <Formula 2>

   

   <Formula 3>

   

   <Formula 4>

   

   <Formula 5>

   

   <Formula 6>

   

   In Formulas 2 to 6,

   * indicates the position combined with Y, X ₁ or X ₂

   _{X 3 and _ _ _ _} One and

   R ₁ to R ₉ are each independently hydrogen, deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, trimethylsilylethynyl group (TMS), substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Alkynyl group, substituted or unsubstituted cycloalkenyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 3 to 30 carbon atoms Heteroaryl group of 30, substituted or unsubstituted amine group, substituted or unsubstituted alkylamino group of 1 to 30 carbon atoms, substituted or unsubstituted aralkylamino group of 7 to 30 carbon atoms, substituted or unsubstituted aralkylamino group of 6 to 30 carbon atoms arylamino group, substituted or unsubstituted heteroarylamino group having 3 to 30 carbon atoms, substituted or unsubstituted silyl group, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 6 to 30 carbon atoms Arylsilyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms and substituted or unsubstituted One selected from arylthio groups having 6 to 30 carbon atoms,

   Optionally, two adjacent groups among R ₁ to R ₉ may be combined with each other to form a carbon ring structure,

   Optionally, when each of R ₁ to R ₉ is substituted, the substituents are each independently deuterium, cyano group, trifluoromethyl group, nitro group, halogen group, hydroxy group, trimethylsilylethynyl group (TMS), and carbon number 1. Alkyl group with 3 to 30 carbon atoms, cycloalkyl group with 3 to 20 carbon atoms, alkenyl group with 2 to 30 carbon atoms, cycloalkenyl group with 3 to 20 carbon atoms, alkynyl group with 2 to 30 carbon atoms, cycloalkenyl group with 3 to 20 carbon atoms, 6 to 6 carbon atoms Aryl group of 30, aralkyl group of 7 to 30 carbon atoms, heteroaryl group of 3 to 30 carbon atoms, heteroaralkyl group of 3 to 30 carbon atoms, amine group, alkylamino group of 1 to 30 carbon atoms, aralkylamino group of 7 to 30 carbon atoms , arylamino group with 6 to 30 carbon atoms, heteroarylamino group with 3 to 30 carbon atoms, silyl group, alkylsilyl group with 1 to 30 carbon atoms, arylsilyl group with 6 to 30 carbon atoms, alkoxy group with 1 to 30 carbon atoms, 6 to 6 carbon atoms. It may be one or more selected from the group consisting of an aryloxy group having 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, and an arylthio group having 6 to 30 carbon atoms, and when there are multiple substituents, the substituents may be the same or different from each other. organic compounds.
2. According to paragraph 1,

   Wherein R ₁ to R ₉ are each independently hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted butyl group, or a substituted or unsubstituted group. Butyl group, substituted or unsubstituted isobutyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthalenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted fluorene group, substituted or unsubstituted spirofluorene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted furan group, substituted or unsubstituted Thiophene group, substituted or unsubstituted carbazole group, substituted or unsubstituted diphenylamine group, substituted or unsubstituted pyridine group, substituted or unsubstituted pyrimidine group, substituted or unsubstituted piperidine group and substituted or An organic compound selected from the group consisting of an unsubstituted acridine group.
3. According to paragraph 1,

   The formula 1 is an organic compound represented by the formula 7 below.

   <Formula 7>

   
4. According to paragraph 1,

   The organic compound of Formula 1 is represented by one selected from the group consisting of Formulas 8 to 11 below.

   <Formula 8>

   

   <Formula 9>

   

   <Formula 10>

   

   <Formula 11>

   
5. According to paragraph 1,

   The organic compound of Formula 1 is represented by one selected from the group consisting of Formulas 12 to 15 below.

   <Formula 12>

   

   <Formula 13>

   

   <Formula 14>

   

   <Formula 15>

   
6. According to paragraph 4,

   The organic compound wherein X ₃ and X ₄ are each independently either oxygen (O) or sulfur (S).
7. According to paragraph 1,

   The compound represented by Formula 1 is, An organic compound selected from the group consisting of Compounds 1 to 286 below:

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   

   .
8. first electrode;

   a second electrode facing the first electrode; and

   It includes an organic layer disposed between the first electrode and the second electrode,

   The organic layer includes a light-emitting layer,

   The light-emitting layer is an organic light-emitting device comprising the organic compound according to any one of claims 1 to 7.
9. According to clause 8,

   The light-emitting layer is a blue light-emitting layer,

   An organic light-emitting device wherein the organic compound is used as a dopant of the blue light-emitting layer.
10. According to clause 9,

    CIEx of the color coordinate of the blue light-emitting layer is 0.10 to 0.15, and CIEy is 0.03 to 0.10.
11. According to clause 8,

    The organic layer is at least one selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron suppression layer, a light emission auxiliary layer, a charge generation layer, a hole suppression layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer. An organic light emitting device that further includes.
12. According to clause 8,

    The organic light emitting device may include a flat panel display device; flexible display device; Devices for monochromatic or white flat panel lighting; Devices for flexible lighting in single color or white; Vehicle display devices; And an organic light emitting device used in any one device selected from the group consisting of a display device for virtual or augmented reality.