KR20220155118A - Organic electroluminescent device comprising polycyclic compounds - Google Patents

Abstract

The present invention relates to an organic electroluminescent element including a polycyclic compound and, more specifically, to an organic electroluminescent element which comprises: a first electrode; a second electrode; and a light emitting layer formed between the first electrode and the second electrode. A hole injection layer, a hole transport layer, and a light emitting auxiliary layer are sequentially stacked between the first electrode and the light emitting layer, and at least one of the hole injection layer, the hole transport layer, and the light emitting auxiliary layer includes a compound represented by chemical formula 1A. The compound represented by chemical formula 1A is as defined in claim 1.

Description

Organic electroluminescent device containing a polycyclic compound {ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING POLYCYCLIC COMPOUNDS}

The present invention relates to an organic electroluminescent device including a polycyclic compound.

An organic light emitting diode is a self-luminous display device that displays an image using an organic light emitting material. Unlike the existing liquid crystal display (LCD), it does not require a separate light source, so it can be made relatively thin, so it can be said to be a suitable technology for flexible device devices (flexible light emitting displays) in the future. Organic light emitting material is a chemical substance that converts electrical energy into light energy to help display an image on a display. In an organic light emitting device, it is placed between a first electrode or anode and a second electrode or cathode to improve the stability and efficiency of the chemical substance. to form a multi-layered organic material layer. The organic layer suitable for the above technology may have different names depending on the characteristics, and examples include a hole injection layer, a hole transport layer, a light emitting layer host, a light emitting layer dopant, an electron transport layer, and an electron injection layer. The organic layer may be classified into a polymer light emitting layer and a low molecular weight light emitting layer according to molecular weight, and may be classified into a fluorescence light emitting layer and a phosphorescent light emitting layer according to the mechanism of the light emitting layer. The light emitting phenomenon of the organic light emitting device is that holes injected from the anode move to the light emitting layer by the hole transport layer and combine with electrons injected from the cathode to emit light. Here, light emission from a singlet excited state is called fluorescence, and light emission from a triplet excited state is called phosphorescence. The ratio of fluorescence and phosphorescence can be said to be 25%:75%, and a phosphorescent material is used as a dopant to implement a display device with high efficiency and long lifespan. Recently, cases in which delayed fluorescent organic chemicals are applied as dopants in order to utilize light emitting mechanisms such as phosphorescence are often reported.

In addition, the light emitting material implements a display device with a high color gamut by utilizing three elements of blue, green, and red light. According to a recently reported technology, white light is created by mixing blue, yellow, or orange materials in a large-area display device, and blue, green, and red materials are applied to a small display device. In order to improve the efficiency of the light emitting layer material, a host and a dopant are mixed and used at a constant ratio. When only one type of material is used, the maximum emission wavelength is color shifted to a longer wavelength due to the interaction between compounds, that is, between molecules, thereby improving color purity and This is to solve a problem in which attenuation of luminous efficiency may occur. That is, when a small amount of a dopant material having a narrow band gap is added to a host material having a wide energy band gap, excitons generated in the light emitting layer are transferred to the dopant, thereby obtaining a display device with high efficiency. It is characterized by being able to produce various colors depending on the dopant material having a narrow band gap.

The light emission process in an organic light emitting device is 1) injection of charges (holes, electrons), 2) transfer of charges, 3) charge recombination, 4) generation of light (phosphorescence, fluorescence), 5) light to the outside of the device. goes through the release phase of In order to improve device efficiency, research is being conducted on internal efficiency improvement through balanced charge transfer speed, minimization of leaked charges, improvement of exciton formation rate, and external efficiency improvement through optical compensation using light travel distance. . Based on the above, the efficiency of the organic light emitting device can be expressed as (1):

(1) η _ext (external luminous efficiency) = η _int (internal luminous efficiency) X η _out (light extraction efficiency)

η _int is a process in which the injected electrons and holes recombine, and refers to the formation of a molecular exciton or molecular excited state, which is an electron-hole pair, and the charges that do not participate in recombination It does not contribute to the effect on the generation of light and appears only as a current component. Efficiency by recombination can be expressed by fluorescence and phosphorescence as described above. η _out means the rate at which photons generated inside the device escape out of the device. η _ext is the difference between η _int and η _out As a result, it means the ratio of injected electrons and holes to light coming out of the device. The internal luminous efficiency is how efficiently excitons are generated in an organic layer interposed between a first electrode (eg, anode) and a second electrode (eg, cathode) such as a hole transport layer, a light emitting layer, and an electron transport layer to convert light. It is known that the light conversion rate is theoretically 25% for fluorescence and 100% for phosphorescence. The external luminous efficiency represents the efficiency with which light generated in the organic layer is extracted to the outside of the organic light emitting device, and it is known that a level of about 20% of the internal luminous efficiency is extracted to the outside.

In order to realize high efficiency and high color gamut, 1) energy level and 2) charge mobility of the surrounding layers of the light emitting layer should be considered. It is most important to increase the exciton formation rate in the light emitting layer by controlling the mobility of holes and electrons injected from the electrode. In order to prevent not only the formation of excitons but also their transition to the surrounding layers, the energy level of the lowest unoccupied molecular orbital (LUMO) of the hole transport layer is high compared to the energy level of the light emitting layer, or the highest occupied molecular orbital of the electron transport layer ( HOMO, Highest Occupied Molecular Orbital) should be placed at the lowest energy level. In addition, it has recently been found that the triplet energy level of the surrounding layer affects the luminous efficiency. Therefore, in order to realize a device with high efficiency and long lifespan, it is required to develop a material having a high triplet energy level and a high minimum unoccupied orbital (LUMO) value, and to utilize this, the development of an organic light emitting device with high efficiency and long lifespan is required. .

The present invention is to solve the above problems, to provide an organic electroluminescent device containing a low molecular weight polycyclic compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity and lifetime of the device.

The present invention provides a method for manufacturing an organic electroluminescent device according to the present invention.

However, the problem to be solved by the present invention is not limited to those mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.

According to one embodiment of the present invention, the first electrode; a second electrode; and a light emitting layer formed between the first electrode and the second electrode, wherein a hole injection layer, a hole transport layer and a light emitting auxiliary layer are sequentially stacked between the first electrode and the light emitting layer, and the hole injection layer and the hole injection layer are sequentially stacked. At least one of the transport layer and the light emitting auxiliary layer relates to an organic electroluminescent device comprising a compound represented by Formula 1A below.

[Formula 1A]

In Formula 1A,

L is a direct bond or a substituted or unsubstituted C ₆ ~ C ₆₀ monocyclic or polycyclic cyclic compound, or a substituted or unsubstituted C ₅ ~ C ₆₀ diatomic monocyclic or polycyclic cyclic compound;

Ar ₁ , Ar ₂ Ar ₃ are each selected from substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic cyclic compounds and substituted or unsubstituted C ₅ to C ₆₀ diatomic single or polycyclic cyclic compounds; ,

R ₁₁ , R ₁₂ , R ₂₁ , and R ₂₂ are, respectively, hydrogen, heavy hydrogen, a halogen group, a nitro group, a cyano group, a C ₁ to C ₅₀ alkyl group, a C ₁ to C ₅₀ alkenyl group, a C ₁ to C ₅₀ alkynyl group, C ₁ ~C ₅₀ alkoxy group, C ₁ ~C ₅₀ silyl group, substituted or unsubstituted C ₆ ~C ₆₀ monocyclic or polycyclic ring compound, and substituted or unsubstituted C ₅ ~C It is selected from ₆₀ diatomic single or polycyclic cyclic compounds,

a is an integer from 0 to 4;

b is an integer from 0 to 2;

The substitution is heavy hydrogen, a halogen group, a hydroxyl group (-OH), a nitro group, a cyano group, a C ₁ ~ C ₅₀ alkyl group, a C ₁ ~ C ₅₀ alkenyl group, a C ₁ ~ C ₅₀ alkynyl group, C ₁ ~ C ₅₀ alkoxy group, C ₆ ~ C ₅₀ aryl group, C ₅ ~ C ₅₀ heteroaryl group, C ₁ ~ C ₅₀ is selected from an alkylsilyl group and C ₆ ~ C ₅₀ arylsilyl group. )

According to an embodiment of the present invention, Ar ₂ and Ar ₃ may be the same as or different from each other.

According to an embodiment of the present invention, at least one or more of the hole injection layer, the hole transport layer, and the light emitting auxiliary layer may include at least one or more of Chemical Formulas 1 to 582 of the present invention.

According to an embodiment of the present invention, the hole injection layer includes the compound represented by Chemical Formula 1A and a p-dopant, and the lowest unoccupied orbital function (LUMO) value of the p-dopant is -4.8 eV or less. can

According to an embodiment of the present invention, the p-dopant in the hole injection layer is 0.5% to 50% by weight, and the ratio (w/w) of the compound represented by Formula 1A to the p-dopant is, It may be 99.5: 0.5 to 50: 50.

According to one embodiment of the present invention, the substituent parent of the p-dopant is at least one selected from the group consisting of substituted or unsubstituted benzene, naphthalene, phenanthrene, anthracene, radialene, dibenzofuran, and dibenzothiophene. It may contain more than one.

According to an embodiment of the present invention, the substituent of the p-dopant may include at least one of Chemical Formulas p1 to Chemical Formula p18.

[Formula p1 to Formula p18]

According to an embodiment of the present invention, the hole injection layer, the hole transport layer, or both may include a tertiary aryl amine having a highest occupied orbital function (HOMO) value of -4.8 eV to -5.8 eV. have.

According to an embodiment of the present invention, sequentially forming a hole injection layer, a hole transport layer and an auxiliary light emitting layer on the first electrode; forming a light emitting layer on the light emitting auxiliary layer; and forming a second electrode layer on the light emitting layer. Including, wherein at least one of the hole injection layer, the hole transport layer and the light emitting auxiliary layer includes at least one of the compounds represented by Formula 1A according to the present invention, a method for manufacturing an organic electroluminescent device It is about.

In the present invention, an organic light emitting device having high efficiency, low voltage, high color purity and long lifespan can be implemented by applying a low molecular weight material having a high lowest unoccupied molecular orbital energy level and a high triplet energy level. In addition, the present invention may provide an organic light emitting device as well as an electronic device including the organic light emitting device.

1 is a cross-sectional view of an organic light emitting device structure according to an exemplary embodiment of the present invention.

Hereinafter, embodiments will be described in detail with reference to the accompanying drawings. However, since various changes can be made to the embodiments, the scope of the patent application is not limited or limited by these embodiments. It should be understood that all changes, equivalents or substitutes to the embodiments are included within the scope of rights.

Terms used in the examples are used only for descriptive purposes and should not be construed as limiting. Singular expressions include plural expressions unless the context clearly dictates otherwise. In this specification, terms such as "include" or "have" are intended to designate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, but one or more other features It should be understood that the presence or addition of numbers, steps, operations, components, parts, or combinations thereof is not precluded.

Unless defined otherwise, all terms used herein, including technical or scientific terms, have the same meaning as commonly understood by a person of ordinary skill in the art to which the embodiment belongs. Terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with the meaning in the context of the related art, and unless explicitly defined in the present application, they should not be interpreted in an ideal or excessively formal meaning. don't

In addition, in the description with reference to the accompanying drawings, the same reference numerals are given to the same components regardless of reference numerals, and overlapping descriptions thereof will be omitted. In describing the embodiment, if it is determined that a detailed description of a related known technology may unnecessarily obscure the gist of the embodiment, the detailed description will be omitted.

Also, terms such as first, second, A, B, (a), and (b) may be used in describing the components of the embodiment. These terms are only used to distinguish the component from other components, and the nature, order, or order of the corresponding component is not limited by the term.

Components included in one embodiment and components having common functions will be described using the same names in other embodiments. Unless stated to the contrary, descriptions described in one embodiment may be applied to other embodiments, and detailed descriptions will be omitted to the extent of overlap.

Hereinafter, the organic light emitting device of the present invention and its manufacturing method will be described in detail with reference to examples and drawings. However, the present invention is not limited to these examples and drawings.

The present invention relates to an organic electroluminescent device including a polycyclic compound, and according to an embodiment of the present invention, the polycyclic compound may include a compound represented by Chemical Formula 1A below. The polycyclic compound and/or its derivative represented by Chemical Formula 1A is a low molecular weight compound applied to an organic material layer of an organic light emitting device, and can provide an organic light emitting device having improved light efficiency and color purity and long lifespan.

[Formula 1A]

In Formula 1A,

As an example of the present invention, L is a direct bond, or a substituted or unsubstituted C ₆ ~ C ₆₀ monocyclic or polycyclic cyclic compound, or a substituted or unsubstituted C ₅ ~ C ₆₀ diatomic single or polycyclic cyclic compound. can

As an example of the present invention, Ar ₁ , Ar ₂ and Ar ₃ are each a substituted or unsubstituted C ₆ ~ C ₆₀ monocyclic or polycyclic cyclic compound and a substituted or unsubstituted C ₅ ~ C ₆₀ diatomic monocyclic compound. or a polycyclic compound, and Ar ₁ , Ar ₂ and Ar ₃ may be the same as or different from each other. Also, Ar ₂ and Ar ₃ may be the same as or different from each other.

As an example of the present invention, R ₁₁ , R ₁₂ , R ₂₁ , and R ₂₂ are each selected from hydrogen, deuterium, a halogen group, a nitro group, a cyano group, a C ₁ ~ C ₅₀ alkyl group, and a C ₁ ~ C ₅₀ alky group. Nyl group, C ₁ ~ C ₅₀ alkynyl group, C ₁ ~ C ₅₀ alkoxy group, C ₁ ~ C ₅₀ silyl group, substituted or unsubstituted C ₆ ~ C ₆₀ monocyclic or polycyclic ring compound and substituted or unsubstituted It may be selected from cyclic C ₅ ~ C ₆₀ diatomic monocyclic or polycyclic cyclic compounds.

As an example of the present invention, a is an integer of 0 to 4, b is an integer of 0 to 2, and a and b may be the same as or different from each other.

As an example of the present invention, the “single and polycyclic cyclic compound” may include an aromatic hydrocarbon ring, a non-aromatic hydrocarbon ring, or both. The “polycyclic cyclic compound” may be one in which a plurality of identical or different rings are condensed or directly linked by a linking group and/or a linking group. Preferably, “single and polycyclic cyclic compounds” may be selected from the following chemical formulas composed of one or more aromatic hydrocarbon rings, but are not limited thereto. At least one atom in the ring of the formula below may be substituted by a single or multiple substituents (R) that are the same or different. At least one or more atoms in the ring, other than the atoms linked and/or bonded to the parent and/or moiety of Formula 1A, are substituted by a substituent (R), and correspond to such a linkage and/or bonded site. Atoms in the ring may be directly linked and/or bonded or may utilize a linking group (R').

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(Where R is a substituent, and will be described in more detail below. c is 0, 1 or more, and less than or equal to the maximum number of atoms in which substituents can be introduced in the entire ring in the above formula. R' is a linking group, and In more detail, d is 0 or 1 to 2.

R is applied to at least one or more or all of the entire rings in the above formula, and within the c value, in whole or in part, consists of the same or different substituents,

R' applies to at least one or more or all of the entire rings in the above formula, and within the d value, all or part may consist of the same or different linking groups.

R'' and R''' are each selected from substituents and linking groups, and e and f are 0 or 1, respectively.

X is selected from C, N, S and O.)

As an example of the present invention, the diatom in the ring may include at least one or more of N, S, and O, and is selected from, for example, N1 to N4, S1 to S3, O1 to O3, or a combination thereof, The number of diatoms may be the number of diatoms included in the entire cyclic compound or at least one ring in the cyclic compound.

As an example of the present invention, the substituents (or R, R″ and R″) are deuterium, a halogen group, a hydroxyl group (-OH), a nitro group, a cyano group, a C ₁ ~ C ₅₀ alkyl group , C ₁ ~ C ₅₀ alkenyl group, C ₁ ~ C ₅₀ alkynyl group, C ₁ ~ C ₅₀ alkoxy group, C ₆ ~ C ₅₀ aryl group, C ₅ ~ C ₅₀ heteroaryl group and C ₁ ~ It may be selected from one or more selected from C ₅₀ silyl groups. Preferably, the substituent is a deuterium, a halogen group, a hydroxyl group (-OH), a nitro group, a cyano group, a C ₁ ~ C ₂₀ alkyl group, a C ₁ ~ C ₂₀ alkenyl group, a C ₁ ~ C ₂₀ alky It may be selected from a yl group, a C ₁ ~ C ₂₀ alkoxy group, a C ₆ ~ C ₃₀ aryl group, a C ₅ ~ C ₃₀ heteroaryl group, and a C ₁ ~ C ₃₀ silyl group.

For example, in the above substitution, a substituent is introduced to at least one of carbon and diatomic atoms in the ring, and all or at least one ring in the polycyclic compound may be substituted.

For example, the silyl group may be selected from a C ₁ ~C ₅₀ alkylsilyl group and a C ₆ ~C ₅₀ arylsilyl group.

For example, the “alkyl”, “alkenyl” and “alkynyl” are straight-chain or branched-chain hydrocarbons, and the alkyl is C ₁ to C ₅₀ ; C ₁ to C _30; C ₁ to C ₂₀ ; or C ₁ ~ C ₁₀ Alkyl, and the alkenyl is C ₂ ~ C ₅₀ ; C ₂ to C ₃₀ ; C ₂ to C ₂₀ ; or C ₂ ~ C ₁₀ alkenyl, and the alkynyl is C ₂ ~ C ₅₀ ; C ₂ to C ₃₀ ; C ₂ to C ₂₀ ; or C ₂ ~C ₁₀ alkynyl.

For example, the alkoxy group corresponds to -OR, and R may be selected from a C ₁ ~ C ₅₀ alkyl group, a C ₂ ~ C ₅₀ alkenyl group, and a C ₆ ~ C ₅₀ aryl group.

For example, the C ₅ ~ C ₅₀ heteroaryl group may include at least one or more of N, S, and O, and may include, for example, N1 to N4, S1 to S3, O1 to O3, or a combination thereof. selected, and a single aromatic hydrocarbon ring or a plurality of aromatic hydrocarbon rings may be connected or condensed.

As an example of the present invention, the linking group (or, R', R'' and R''') is a substituted or unsubstituted C ₆ ~ C ₅₀ single or polycyclic aromatic hydrocarbon ring, and two or more aromatic hydrocarbon rings is in a condensed or condensed form. One or more, or two or more atoms of the entire ring of the linking group corresponds to the linking portion of the parent and/or moiety in Formula 1A.

As an example of the present invention, the compound represented by Chemical Formula 1A may be selected from at least one or more compounds of Chemical Formulas 1 to 582 below. For example, at least one or more of the organic material layers included between the first electrode and the second electrode may include at least one or more compounds of Chemical Formulas 1 to 582 below.

[Formula 1 to Formula 582]

According to an embodiment of the present invention, the organic light emitting device includes a support substrate, a first electrode, a second electrode, and several organic material layers on the first electrode and the second electrode, and the first electrode and the second electrode. One or more organic material layers, ie, a capping layer, located opposite to the organic material layer of the electrode may be further included.

As an example of the present invention, an organic material layer positioned between the first electrode and the second electrode and a light emitting layer such as blue, green, red, yellow, etc. may be individually or mixed, and the organic material layer may include an electron injection layer, an electron transport layer, and a hole hole. It may include an injection layer, a hole transport layer and a light emitting auxiliary layer.

As an example of the present invention, in the organic light emitting device, a capping layer may be sequentially formed on a support substrate, a first electrode, a first organic material layer, a light emitting layer, a second organic material layer, a second electrode layer, and the second electrode layer. For example, as shown in FIG. 1, in the first organic material layer, a hole injection layer, a hole transport layer, and a light emitting auxiliary layer are sequentially stacked, and in the second organic material layer, an electron transport layer and an electron injection layer are sequentially stacked. can The first organic material layer and the second organic material layer may be composed of all organic materials or may further include a metal, a metal oxide, or a metal ion in part based on the organic material.

According to one embodiment of the present invention, the supporting substrate may use a supporting substrate used in a conventional organic light emitting device. The support substrate may be formed of a sapphire substrate, a wafer, a glass substrate, or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, while being made of an opaque material such as silicon or stainless steel. may be formed. For example, as the glass substrate, glass such as soda lime glass, alkali-free glass, high strain point glass (PD200, etc.) may be used, and as the transparent plastic, polyethersulfone (PES), polyacrylate (PAR) , polyetherimide (PEI), polyethylene naphthalate (PEN), polyethylene terephthalate (PET), polyphenylene sulfide (PPS), polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP) and the like.

According to one embodiment of the present invention, the first electrode is formed on a support substrate, and may be an anode or a cathode, preferably an anode (anode). At this time, the first electrode may be a reflective electrode, and is formed by coating a material for an anode on a support substrate in a conventional method. The first electrode is made of silver (Ag), zinc (Zn), copper (Cu), vanadium (V), magnesium (Mg), aluminum (Al), platinum (Pt), lead (Pd), gold, nickel ( A reflective film formed of Ni), molybdenum (Mo), neodymium (Nd), iridium (Ir), chromium (Cr), an alloy thereof or an oxide thereof, and a transparent or translucent film having a high work function formed on the reflective film An electrode layer may be provided, and when used as an anode, a material having a large work function may be used so that hole injection into the highest occupied orbital function of the organic material layer can be easily performed. Preferably, the transparent or translucent electrode layer is, for example, Molybdenum titanium alloy, indium oxide, ITO (indium tin oxide), IZO (indium zinc oxide), ZnO (zinc oxide), AZO (aluminum zinc oxide), IGO (indium gallium oxide), In ₂ O ₃ (indium oxide), It may include at least one selected from the group consisting of SnO ₂ (tin oxide) and arsenic oxide.

As an example of the present invention, in the case of a top emission type organic light emitting device, the first electrode may be made of a metal reflective film material and serves to apply an electric field to the organic light emitting device together with the second electrode. Here, the first electrode serves as an anode, and since the first electrode has excellent reflective properties, it can reflect the light coming from the light emitting layer to the first electrode and send it to the front surface. ) effect can be formed.

According to one embodiment of the present invention, the second electrode may be a cathode or an anode, preferably a cathode (negative electrode). In this case, the second electrode may be a transmissive or transflective electrode. For the second electrode, a metal having a low work function is used as a cathode material so that electrons can be easily injected into the lowest unoccupied orbital function of an organic material. Specific examples include magnesium, calcium, sodium, potassium, titanium, indium, Metal materials such as yttrium, lithium, aluminum, silver, tin, and lead, or multi-layered materials such as LiF/Al or LiO ₂ /Al, which are alloys thereof, are formed to form the electron injection layer, but are not limited thereto. For example, a metal thin film having a low work function including Li, Ca, LiF/Ca, LiF/Al, aluminum, silver, magnesium, or an alloy thereof may be formed. As another example, the second electrode may form a light-transmitting electrode including at least one selected from the group consisting of indium zinc oxide casting, silver, magnesium, and yttrium.

As an example of the present invention, the second electrode is selected from the group consisting of aluminum (Al), platinum (Pt), ytterbium (Yb), neodymium (Nd) and magnesium (Mg) based on 100 parts by weight of silver (Ag) One or more second metals may be further included within the range of 50 parts by weight. By being made of a mixture containing silver (Ag) and the second metal, thin film properties such as transparency of the second electrode can be improved. When the content of the second metals satisfies the above range, the driving voltage does not rise because light absorption and resistance are appropriate.

According to an embodiment of the present invention, at least one of the hole injection layer, the hole transport layer, and the light emitting auxiliary layer in the first organic material layer includes a p-type dopant, and preferably, the hole injection layer is a p-type Dopants may be included. In addition, at least one or more of the hole injection layer, the hole transport layer, and the light emitting auxiliary layer may include at least one or more polycyclic compounds represented by Chemical Formula 1 according to the present invention.

As an example of the present invention, in the first organic material layer, that is, the hole injection layer, the p-dopant may be included in an amount of 0.5% to 50% by weight. In addition, the ratio of the polycyclic compound represented by Chemical Formula 1 to the p-dopant in the first organic material layer, that is, the hole injection layer, is 99.5:0.5 to 50:50 (w/w); 99.5 : 0.5 to 80 : 20 (w/w); 99.5 : 0.5 to 90 : 10 (w/w); Or it may be 99.5: 0.5 to 95: 5 (w/w), and the above range may be expressed as “below”, “greater than”, “less than” or “exceeded” if it does not deviate from the object and scope of the present invention. have.

As an example of the present invention, the hole injection layer may include a material having a low lowest unoccupied molecular orbital value. For example, the compound represented by Chemical Formula 1A and a p-dopant may be included, and the lowest unoccupied orbital (LUMO) value of the p-dopant may be -4.8 eV or less.

As an example of the present invention, the parent of the p-dopant substituent is at least one selected from the group consisting of substituted or unsubstituted benzene, naphthalene, phenanthrene, anthracene, radialene, dibenzofuran, and dibenzothiophene. and the p-dopant substituent may include at least one or more of the compounds having the following Chemical Formula p1 to Chemical Formula p18.

[Formula p1 to Formula p18]

As an example of the present invention, the hole injection layer may apply a hole injection material known in the art of the present invention, but in order to minimize the difference in energy level with the anode, tertiary nitrogen such as an aromatic ring amine is included. organic substances are mainly used, such as m-MTDATA [4,4',4"-tris(3-methylphenylphenylamino) triphenylamine], DNTPD (N1,N1-(biphenyl-4,4-diyl)bis(N1 -phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), ΝΝΡΒ(Ν,Ν'-di(1-naphthyl)-Ν, Ν'-diphenylbenzene (N,N'-di (l-naphthyl)-N,N'-diphenylbenzidine)), TDATA, 2T-NATA, etc. In addition, a specific example of the metal complex compound is a copper phthalocyanine compound, which has the lowest unoccupied orbital function. As a material, F4TCNQ (2,3,5,6-Tetrafluoro-tetracyanoquinodimethane) is used to dope the phenylene-based HATCN (Hexaazatriphenylenehexacarbonitrile) and the organic material with the lowest unoccupied orbital in the tertiary aromatic ring compound in the host and dopant form. Derivatives and the like may be used, but are not limited thereto.

As an example of the present invention, the hole injection layer, the hole transport layer, or both may include a tertiary aryl amine having a highest occupied orbital function (HOMO) value of -4.8 eV to -5.8 eV. For example, the hole transport layer may include tertiary aryl amine in consideration of the correlation between the hole injection layer and the highest occupied orbital function of the light emitting layer. The tertiary aryl amine may be spirobifluorene, fluorene, dibenzofuran, dibenzothiophene, or a carbazole derivative, for example, spiro-BPA (spirofluorne derivative) 2,2'-Bis(N,N-di-phenyl-amino)-9,9-spirobifluorene), MeO-spiro-TPD(2,7-Bis[N,N-bis(4-methoxy-phenyl)amino ]-9,9-spirobifluorene), spiro-NPBN (7-Di-1-naphthalenyl-N 2 , N 7 -diphenyl-9,9'-spirobi [9H-fluorene] -2,7-diamine), etc. , but not limited thereto.

As an example of the present invention, the light emitting auxiliary layer may include at least one of the compounds represented by Chemical Formula 1A according to the present invention, and a light emitting layer may be formed on the light emitting auxiliary layer.

According to an embodiment of the present invention, the light emitting layer may be formed using various known light emitting materials, but may also be formed using a known host and dopant. As the dopant, a known fluorescent dopant or a known phosphorescent dopant may be used. For example, the light emitting layer may include a fluorescent dopant including an arylamine substituent; A delayed fluorescence dopant containing a boron ring compound or a nitrile group; And phosphorescent dopants containing iridium or platinum complex compounds; may include at least one or more selected from the group consisting of, but is not limited thereto. As the light emitting layer, a fluorescent light emitting material may be used for blue, and an iridium complex compound, which is a transition metal, may be used for green, red, and yellow. The emission layer may be composed of red (R), green (G), and blue (B) colors for each sub-pixel.

According to an embodiment of the present invention, the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, and the electron transport layer correspond to organic material layers, and the total thickness of the organic material layer is at a thickness of 1,000 Å to 10,000 Å can be chosen

According to one embodiment of the present invention, the second organic material layer may include an electron injection layer and an electron transport layer. For the electron transport layer and the electron injection layer, an electron transport material or an electron injection material known in the art may be applied. For example, the electron transport material may include pyridine, benzoxazole, quinoline, triazine, and the like. Cyclic compounds containing the same closed nitrogen are mainly used. Specific examples include Bphen (4,7-diphenyl-l,10-phenanthroline), TAZ (3-(biphenyl-4-yl)-5-(4-tertbutylphenyl)-4-phenyl-4H-1,2,4- triazole), 2-(4-(9,10-di(naphthalene-2-yl)anthrancene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, etc.,: Alq ₃ (tris-( 8-hydroxyquinoline) may include at least one or more selected from the group consisting of complex compounds with inorganic substances such as aluminum) and combinations thereof, but is not limited thereto.

According to one embodiment of the present invention, the first organic material layer, the light emitting layer, and the second organic material layer are composed of single or multiple layers, and when composed of multiple layers, thickness, type of component, component ratio or concentration, etc. may be the same or different.

According to an embodiment of the present invention, a capping layer contacting the first electrode, the second electrode, or both may be further included. Preferably, it may be formed on the second electrode, and it may improve viewing angle characteristics, increase external light emitting efficiency, and increase heat resistance and luminance stability. In addition, the capping layer may serve to prevent deterioration of the lower electrode and the organic layer from external moisture or oxygen.

As an example of the present invention, the capping layer may include an organic material, an inorganic material, or a mixture thereof, and the capping layer may be formed in two or more layers by alternately using a material having a high refractive index and a material having a small refractive index. By forming the capping layer in multiple layers, an effect of increasing light extraction efficiency may be obtained by constructive interference. Light passing through the capping layer is reflected at the interface between the capping layer and the external air layer, goes to the surface of the second electrode, and is reflected again to the outside through the capping layer, causing interference due to a difference in path. As a result, the amount of light lost through total reflection is reduced and the amount of transmitted light is increased, thereby increasing luminous efficiency. Since each red, green, and blue pixel has a different wavelength range of light emitted from each other, a region of the capping layer corresponding thereto may have various thicknesses, and the range may be 10 nm to 150 nm. When the thickness of the capping layer is 10 nm or more, the ability to extract light to the outside is exhibited, and when the thickness is 150 nm or less, the absorption of the capping layer itself is not too great, so the light efficiency is excellent.

As an example of the present invention, by forming the capping layer on the first electrode or the second electrode, it is possible to improve the efficiency and color purity by adjusting the optimal light efficiency distance. When located on the second electrode, through the capping layer, the second electrode of the organic light emitting device is stabilized and the electron injection characteristics are improved to increase the light transmittance and improve the driving voltage and efficiency of the organic light emitting device. effect can be obtained. In addition, preferably, a second electrode containing silver (Ag) may be formed under the capping layer, and the second electrode may transmit light while reflecting some light. The second electrode, such as Mg-Ag, may have low light absorption and high transmittance and reflectivity compared to conventional electrodes.

The present invention relates to a method for manufacturing an organic light emitting device according to the present invention, and according to one embodiment of the present invention, forming a first electrode, forming a first organic material layer; Forming a light emitting layer; forming a second organic material layer; and forming a second electrode layer, and may further include forming a capping layer on the first electrode, the second electrode, or both.

As an example of the present invention, the forming of the first electrode is a step of forming a first electrode layer on a support substrate, and the step of forming the first organic material layer is sequentially on the first electrode, a hole injection layer, Forming a hole transport layer and a light emitting auxiliary layer, and more specifically, forming a hole injection layer on the first electrode; forming a hole transport layer on the hole injection layer; Forming a light emitting auxiliary layer on the hole transport layer may be included. At least one of the hole injection layer, the hole transport layer, and the light emitting auxiliary layer may include a polycyclic compound and/or a derivative thereof according to the present invention.

As an example of the present invention, the step of forming the first organic material layer includes forming a layer including the polycyclic compound and/or a derivative thereof according to the present invention. A coating composition may be used. As an example of the present invention, the coating composition is applied to an organic layer of an organic light emitting device, for example, at least one of a hole injection layer, a hole transport layer, and a light emitting auxiliary layer, which are the first organic layer in the organic light emitting device. can be applied

As an example of the present invention, the coating composition contains the components mentioned in the organic electroluminescent device in order to apply the polycyclic compound and/or its derivative alone or to the hole injection layer, the hole transport layer and the light emitting auxiliary layer according to the present invention, respectively. can include more. The composition may further include solvents (water, organic solvents), additives, etc. applied in the technical field of the present invention to solvent and/or disperse components, but are not specifically mentioned in the present specification.

As an example of the present invention, the step of forming the light emitting layer is a step of forming a light emitting layer on the light emitting auxiliary layer, and the step of forming the second organic material layer is to sequentially form an electron transport layer and an electron injection layer on the light emitting layer. It is a step to For example, forming an electron transport layer on the light emitting layer; and forming an electron injection layer on the electron transport layer.

As an example of the present invention, the step of forming the second electrode is the step of forming the second electrode on the electron injection layer, and the step of forming a capping layer on the second electrode; may further include.

As an example of the present invention, the manufacturing method may use a solution process, deposition, or both methods. For example, the first electrode forming step may use a physical deposition method such as electron beam evaporation on a substrate A metal oxide having conductivity or an alloy thereof may be deposited to form a first electrode, for example, an anode. The forming of the second electrode may be performed as a film forming process using a metal source in a vacuum chamber. Here, by forming the capping layer disclosed in the present invention on the cathode (or anode), the efficiency and color purity are improved by controlling the optimal light efficiency distance.

For example, the formation of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, and the electron transport layer may be performed by vacuum deposition, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, or doctor blade processes. It may be formed by a solution coating method using one or more solutions (or compositions) selected from the group, but is not limited thereto.

As another example, an electron transport layer may be formed on the light emitting layer using various methods such as sputtering, thermal deposition, vacuum deposition, chemical vapor deposition (CVD), spin coating, or spin casting. In the case of forming the electron transport layer by vacuum deposition, spin coating, etc., the deposition conditions and coating conditions vary depending on the compound used, but may generally be selected from the same range of conditions as those for forming the hole injection layer. Finally, an electrode is formed after vacuum deposition of the organic material in several layers. As an example of the electrode, those described above may be used.

Hereinafter, the present invention will be described in detail with reference to the following Examples and Comparative Examples. However, the technical spirit of the present invention is not limited or limited thereby.

[Preparation Example 1] Synthesis of Chemical Formula 1

(1) Synthesis of Compound A-1

After putting 2-bromo-4-chloro-1-iodobenzene (5.00g, 15.8mmol) and phenylboronic acid (2.11g, 17.3mmol) in a two-neck round bottom flask, 120ml of anhydrous tetrahydrofuran was added. Stir after addition. Subsequently, tetrakis(triphenylphosphine)palladium (0.91g, 0.8mmol) and potassium carbonate (30.05g, 217.4mmol) and 120ml of distilled water were refluxed at room temperature for 24 hours. When the reaction is completed, tetrahydrofuran is removed by sublimation, and the resulting solid is filtered out. Thereafter, the filtered solid was dried after removing residual water using magnesium sulfate, and separated by column chromatography to obtain compound A-1 (3.79g, 14.2mmol) (yield: 90%). MS:[M+H] ⁺ =267

(2) Synthesis of Compound A-2

After putting A-1 (3.79g, 14.2mmol) and (2-(methoxycarbonyl)phenyl)boronic acid (2.81g, 15.6mmol) into a two-necked round bottom flask, add 100ml of anhydrous tetrahydrofuran. Stir. Subsequently, tetrakis(triphenylphosphine)palladium (0.82g, 0.7mmol) and potassium carbonate (27.05g, 195.7mmol) and 100ml of distilled water were refluxed at 60 degrees for 24 hours. When the reaction is completed, tetrahydrofuran is removed by sublimation, and the resulting solid is filtered out. Thereafter, the filtered solid was dried after removing residual water using magnesium sulfate, and separated by column chromatography to obtain compound A-2 (3.89g, 12.1mmol) (yield: 85%). MS:[M+H] ⁺ =323

(3) Synthesis of Compound A-4

After putting A-2 (3.89g, 12.1mmol) in a three-necked round bottom flask, 80ml of anhydrous tetrahydrofuran was added and stirred in an ice bath. After slowly injecting a 3.0M methylmagnesium bromide solution (12.05ml, 36.3mmol) over 1 hour while maintaining a low temperature, the mixture was stirred at room temperature for 24 hours. Water was added to complete the reaction, and after layer separation with ethyl acetate, residual water was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound A-3.

After putting A-3 into a two-necked round bottom flask, 30 ml of dichloromethane was added and stirred. Subsequently, boron trifluoride diethyl etherate (1.49ml, 12.1mmol) was slowly injected using a syringe, followed by stirring at room temperature for 24 hours. Thereafter, methanol was added to terminate the reaction, and residual moisture was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound A-4 (2.90 g, 9.5 mmol) (yield: 79%). . MS:[M+H] ⁺ =305

(4) Synthesis of Compound A-5

A-4 (2.90g, 9.5mmol), 4,4,4`,4`, 5,5,5`,5`-octamethyl-2,2`-bi[1,3,2-dioxabo Rolan] (2.66g, 10.5mmol) was put into a two-necked round bottom flask, and then 150ml of anhydrous tetrahydrofuran was added and stirred. Subsequently, potassium acetate (2.80g, 28.6mmol) and tetrakis(triphenylphosphine)palladium [Pd(PPh ₃ ) ₄ ] (1.10g, 1.0mmol) were added, and refluxed at 120°C for 5 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, residual water was removed using magnesium sulfate, dried, and separated by column chromatography to obtain compound A-5 (2.45g, 6.2mmol) (yield: 65%). MS:[M+H] ⁺ =397

(5) Synthesis of Compound 1

A-5 (2.45g, 6.2mmol) and N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1'-biphenyl]-4 -Amine (3.54g, 7.4mmol) was put into a two-necked round bottom flask, and then 50ml of anhydrous tetrahydrofuran was added and stirred. Subsequently, tetrakis(triphenylphosphine)palladium (0.36g, 0.3mmol) and potassium carbonate (11.80g, 85.4mmol) and 50ml of distilled water were refluxed at 90 degrees for 24 hours. When the reaction is completed, tetrahydrofuran is removed by sublimation, and the resulting solid is filtered out. Thereafter, the filtered solid was dried after removing residual moisture using magnesium sulfate, and separated by column chromatography to obtain Compound 1 (3.21g, 4.8mmol) (yield: 78%). MS:[M+H] ⁺ =666

[Preparation Example 2] Synthesis of the compound of Formula 327

In a two-necked flask, A-4 (2.00 g, 6.6 mmol), N-([1,1'-biphenyl]-4-yl)-N-[1,1':4',1''-terphenyl ]-4-amine (2.17 g, 5.5 mmol), sodium-tertiary-butoxide (1.26 g, 13.1 mmol), bis(tri-tertiary-butylphosphine) palladium(0) (0.07 g, 0.1 mmol) After adding toluene (110 mL), the mixture was refluxed at 100 ° C. for 12 hours under a nitrogen stream. After cooling to room temperature, the mixture was diluted with water (100 mL), extracted with dichloromethane, and separated by column chromatography to obtain compound 327 (2.66 g, 4.0 mmol) (yield: 73%). MS:[M+H] ⁺ =666

[Preparation Examples 3-21] Synthesis of Compounds of Chemical Formulas 3-548

Chemical Formula 548 was synthesized in Chemical Formula 3 in the same manner as in the synthesis method of Chemical Formula 1, except for starting materials or intermediate materials. Mass spectrometry of the obtained product is shown in Table 1.

manufacturing example chemical formula MS:[M+H] ⁺ manufacturing example chemical formula MS:[M+H] ⁺ Preparation Example 3 chemical formula 3 742 Production Example 20 chemical formula 245 670 Production Example 4 chemical formula 17 738 Production Example 21 chemical formula 275 831 Preparation Example 5 chemical formula 22 681 Production Example 22 chemical formula 319 729 Preparation Example 6 chemical formula 32 792 Production Example 23 chemical formula 332 666 Preparation Example 7 chemical formula 50 790 Production Example 24 chemical formula 343 595 Preparation Example 8 chemical formula 56 828 Production Example 25 chemical formula 345 671 Production Example 9 chemical formula 64 828 Production Example 26 chemical formula 373 828 Production Example 10 chemical formula 69 828 Production Example 27 chemical formula 414 706 Preparation Example 11 chemical formula 109 748 Production Example 28 chemical formula 419 782 Production Example 12 chemical formula 112 782 Production Example 29 chemical formula 458 680 Preparation Example 13 chemical formula 134 756 Preparation Example 30 chemical formula 460 770 Production Example 14 chemical formula 163 682 Production Example 31 chemical formula 496 696 Production Example 15 chemical formula 167 846 Production Example 32 chemical formula 515 746 Production Example 16 chemical formula 179 756 Production Example 33 chemical formula 539 755 Production Example 17 chemical formula 218 696 Production Example 34 chemical formula 542 679 Preparation Example 18 chemical formula 221 772 Preparation Example 35 chemical formula 548 679 Production Example 19 chemical formula 230 726

[Example 1] Preparation of an organic light emitting device containing Formula 1 as a light emitting auxiliary layer

After washing the ITO with distilled water, it is ultrasonically washed with solvents such as isopropanol, acetone, and methanol, followed by a drying process. Next, after cleaning for 5 minutes using oxygen plasma, the substrate was moved to a vacuum evaporator. HT-1 (100 Å), HT-2 (800 Å), Formula 1 (150 Å) doped with PD-1 (3% by weight) on an ITO electrode, blue host BH1 and dopant BD-1 (3% by weight) The light emitting layer (350 Å), ET1 (350 Å), LiF (10 Å), and Al (1100 Å) were sequentially formed to manufacture an organic light emitting device.

[Examples 2 to 35] Preparation of an organic light emitting device comprising the composition of Table 2 as a light emitting auxiliary layer

Except for using the chemical formula in Table 2 instead of Chemical Formula 1 in Example 1, all other conditions were the same as in Example 1, and a device was manufactured.

Example chemical formula Example chemical formula Example 2 chemical formula 3 Example 19 chemical formula 245 Example 3 chemical formula 17 Example 20 chemical formula 275 Example 4 chemical formula 22 Example 21 chemical formula 319 Example 5 chemical formula 32 Example 22 chemical formula 327 Example 6 chemical formula 50 Example 23 chemical formula 332 Example 7 chemical formula 56 Example 24 chemical formula 343 Example 8 chemical formula 64 Example 25 chemical formula 345 Example 9 chemical formula 69 Example 26 chemical formula 373 Example 10 chemical formula 109 Example 27 chemical formula 414 Example 11 chemical formula 112 Example 28 chemical formula 419 Example 12 chemical formula 134 Example 29 chemical formula 458 Example 13 chemical formula 163 Example 30 chemical formula 460 Example 14 chemical formula 167 Example 31 chemical formula 496 Example 15 chemical formula 179 Example 32 chemical formula 515 Example 16 chemical formula 218 Example 33 chemical formula 539 Example 17 chemical formula 221 Example 34 chemical formula 542 Example 18 chemical formula 230 Example 35 chemical formula 548

[Comparative Example 1]

Except for using HT-2 (150 Å) instead of Chemical Formula 1 in Example 1, all other conditions were the same as in Example 1, and the device was manufactured.

[Example 36] Preparation of an organic light emitting device containing Chemical Formula 1 as a hole injection and hole transport layer

After washing the ITO with distilled water, it is ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, followed by a drying process. Next, the substrate was moved to a vacuum evaporator after cleaning for 5 minutes using oxygen plasma. Formula 1 (100 Å) doped with PD-2 (3% by weight) on an ITO electrode, Formula 1 (700 Å), a light emitting layer of blue host BH1 and dopant BD-1 (3% by weight) (350 Å), ET1 ( 350 Å), LiF (10 Å), and Al (1100 Å) were sequentially formed to manufacture an organic light emitting device.

[Examples 37 to 44] Preparation of an organic light emitting device comprising the configuration of Table 3 as a hole injection and hole transport layer

Except for applying the chemical formula and thickness in Table 2 instead of Chemical Formula 1 in Example 36, all other conditions were the same as in Example 36, and a device was manufactured.

division Hole Injection Layer (HIL) hole transport layer (HTL) Example 37 PD-2 (3%) Formula 1 (97%) Formula 1 (900Å) Example 38 PD-2 (3%) Formula 1 (97%) Formula 1 (1100Å) Example 39 PD-2 (3%) Formula 56 (97%) Formula 56 (900Å) Example 40 PD-2 (3%) Formula 109 (97%) Formula 109 (900Å) Example 41 PD-2 (3%) Formula 163 (97%) Formula 163 (900Å) Example 42 PD-2 (3%) Formula 345 (97%) Formula 345 (900Å) Example 43 PD-2 (3%) Formula 496 (97%) Formula 496 (900Å) Example 44 PD-2 (3%) Formula 539 (97%) Formula 539 (900Å)

[Comparative Examples 2 to 7] Manufacture of an organic light emitting device comprising the configuration of Table 4 as a hole injection and hole transport layer

Except for applying the chemical formula and thickness in Table 3 instead of Chemical Formula 1 in Example 36, all other conditions were the same as in Example 36, and a device was manufactured.

division Hole Injection Layer (HIL) hole transport layer (HTL) Comparative Example 2 PD-2 (3%) HT-1 (97%) HT-1 (700Å) Comparative Example 3 PD-2 (3%) HT-1 (97%) HT-1 (900Å) Comparative Example 4 PD-2 (3%) HT-1 (97%) HT-1 (1100Å) Comparative Example 5 PD-2 (3%) HT-2 (97%) HT-2 (700Å) Comparative Example 6 PD-2 (3%) HT-2 (97%) HT-2 (900Å) Comparative Example 7 PD-2 (3%) HT-2 (97%) HT-2 (1100Å)

[Experimental Example 1]

Electroluminescence wavelength characteristics were observed by applying an electric field of 10 mA/cm ² to the organic light emitting devices of Examples 1 to 35 and Comparative Example 1. The results are shown in Table 5.

division Volt(V) cd/A lm/W CIEx CIEy Example 1 4.15 7.96 6.03 0.139 0.081 Example 2 4.13 7.85 5.97 0.139 0.080 Example 3 4.08 8.11 6.25 0.138 0.082 Example 4 4.16 7.72 5.83 0.140 0.079 Example 5 4.18 7.53 5.66 0.140 0.079 Example 6 4.17 7.67 5.77 0.139 0.080 Example 7 4.24 7.40 5.49 0.140 0.079 Example 8 4.15 7.83 5.92 0.139 0.081 Example 9 4.15 7.95 6.02 0.139 0.082 Example 10 4.12 7.75 5.90 0.139 0.080 Example 11 4.13 7.89 6.01 0.139 0.081 Example 12 4.15 7.77 5.89 0.139 0.081 Example 13 4.17 7.62 5.74 0.139 0.080 Example 14 4.19 7.83 5.87 0.139 0.081 Example 15 4.17 7.83 5.90 0.139 0.081 Example 16 4.14 7.87 5.98 0.139 0.080 Example 17 4.17 7.87 5.93 0.139 0.081 Example 18 4.15 7.87 5.96 0.139 0.081 Example 19 4.05 8.03 6.23 0.139 0.080 Example 20 4.22 8.04 5.99 0.138 0.083 Example 21 4.17 7.69 5.80 0.140 0.079 Example 22 4.16 7.47 5.65 0.140 0.079 Example 23 4.11 7.76 5.94 0.140 0.079 Example 24 4.19 7.87 5.90 0.139 0.081 Example 25 4.15 7.89 5.98 0.139 0.082 Example 26 4.20 7.48 5.60 0.140 0.079 Example 27 4.16 7.59 5.73 0.140 0.079 Example 28 4.15 7.92 6.00 0.139 0.081 Example 29 4.14 7.95 6.03 0.139 0.082 Example 30 4.17 7.82 5.90 0.139 0.081 Example 31 4.13 7.83 5.97 0.139 0.080 Example 32 4.17 7.68 5.79 0.139 0.080 Example 33 4.18 7.73 5.81 0.139 0.080 Example 34 4.20 7.99 5.98 0.138 0.083 Example 35 4.28 7.36 5.40 0.139 0.080 Comparative Example 1 4.61 6.31 4.30 0.140 0.079

[Experimental Example 2]

In Examples 36 to 44 and Comparative Examples 2 to 7, an electric field of 10 mA/cm ² was applied to the organic light emitting device, and the emission wavelength characteristics were observed. The results are shown in Table 6.

division Volt(V) cd/A lm/W CIEx CIEy Example 36 4.09 7.10 5.45 0.140 0.079 Example 37 4.16 7.64 5.78 0.140 0.079 Example 38 4.22 7.51 5.59 0.139 0.080 Example 39 4.19 7.62 5.71 0.140 0.078 Example 40 4.15 7.66 5.79 0.140 0.077 Example 41 4.20 7.62 5.71 0.140 0.078 Example 42 4.16 7.71 5.82 0.140 0.078 Example 43 4.25 7.49 5.53 0.140 0.079 Example 44 4.15 7.76 5.87 0.139 0.080 Comparative Example 2 4.69 5.40 3.62 0.138 0.083 Comparative Example 3 4.73 5.89 3.91 0.139 0.080 Comparative Example 4 4.72 5.72 3.80 0.139 0.081 Comparative Example 5 4.49 6.12 4.28 0.139 0.080 Comparative Example 6 4.48 6.29 4.41 0.139 0.080 Comparative Example 7 4.47 6.20 4.36 0.139 0.080

Referring to Tables 5 and 6, according to the experimental examples of the Comparative Examples and Examples, the compound of Formula 1A of the present invention was injected into a light emitting auxiliary layer or a small amount of p-dopant having a deep lowest unoccupied molecular orbital was added. When an organic light emitting device is manufactured with a layer or a single hole transport layer, the light emitting efficiency and driving voltage are improved due to the characteristics of having a high lowest unoccupied molecular orbital energy level and a high triplet energy level, thereby improving the performance of the organic light emitting device. It can be seen that a significant improvement can be made.

As described above, although the embodiments have been described with limited examples and drawings, those skilled in the art can make various modifications and variations from the above description. For example, even if the described techniques are performed in a different order from the described method, and/or the described components are combined or combined in a different form than the described method, or substituted or substituted by other components or equivalents. Appropriate results can be achieved. Therefore, other implementations, other embodiments, and equivalents of the claims are within the scope of the following claims.

Claims (8)

a first electrode;
a second electrode; and
A light emitting layer formed between the first electrode and the second electrode,
Between the first electrode and the light emitting layer, a hole injection layer, a hole transport layer and a light emitting auxiliary layer are sequentially stacked,
At least one of the hole injection layer, the hole transport layer, and the light emitting auxiliary layer includes a compound represented by Formula 1A below, an organic electroluminescent device:
[Formula 1A]

In Formula 1A,
L is a direct bond or a substituted or unsubstituted C ₆ ~ C ₆₀ monocyclic or polycyclic cyclic compound, or a substituted or unsubstituted C ₅ ~ C ₆₀ diatomic monocyclic or polycyclic cyclic compound;
Ar ₁ , Ar ₂ and Ar ₃ are each selected from substituted or unsubstituted C ₆ to C ₆₀ monocyclic or polycyclic cyclic compounds and substituted or unsubstituted C ₅ to C ₆₀ diatomic single or polycyclic cyclic compounds. becomes,
R ₁₁ , R ₁₂ , R ₂₁ , and R ₂₂ are, respectively, hydrogen, heavy hydrogen, a halogen group, a nitro group, a cyano group, a C ₁ to C ₅₀ alkyl group, a C ₁ to C ₅₀ alkenyl group, a C ₁ to C ₅₀ alkynyl group, C ₁ ~C ₅₀ alkoxy group, C ₁ ~C ₅₀ silyl group, substituted or unsubstituted C ₆ ~C ₆₀ monocyclic or polycyclic ring compound, and substituted or unsubstituted C ₅ ~C It is selected from ₆₀ diatomic single or polycyclic cyclic compounds,
a is an integer from 0 to 4;
b is an integer from 0 to 2;
The substitution is heavy hydrogen, a halogen group, a hydroxyl group (-OH), a nitro group, a cyano group, a C ₁ ~ C ₅₀ alkyl group, a C ₁ ~ C ₅₀ alkenyl group, a C ₁ ~ C ₅₀ alkynyl group, C ₁ ~ C ₅₀ alkoxy group, C ₆ ~ C ₅₀ aryl group, C ₅ ~ C ₅₀ heteroaryl group, C ₁ ~ C ₅₀ is selected from an alkylsilyl group and C ₆ ~ C ₅₀ arylsilyl group. )
According to claim 1,
At least one or more of the hole injection layer, the hole transport layer, and the light emitting auxiliary layer,
An organic electroluminescent device comprising at least one of the following formulas 1 to 582:
[Formula 1 to Formula 582]

According to claim 1,
The hole injection layer includes a compound represented by Chemical Formula 1A and a p-dopant,
The lowest unoccupied orbital function (LUMO) value of the p-dopant is -4.8eV or less,
organic electroluminescent device.
According to claim 3,
The p-dopant in the hole injection layer is 0.5% to 50% by weight,
The ratio (w / w) of the compound represented by Formula 1A to the p-dopant is 99.5: 0.5 to 50: 50,
organic electroluminescent device.
According to claim 3,
The parent of the substituent of the p-dopant,
containing at least one selected from the group consisting of substituted or unsubstituted benzene, naphthalene, phenanthrene, anthracene, radialene, dibenzofuran and dibenzothiophene,
organic electroluminescent device.
According to claim 3,
The substituent of the p-dopant,
An organic electroluminescent device comprising at least one of the following formulas p1 to formula p18:
[Formula p1 to Formula p18]

According to claim 1,
The hole injection layer, the hole transport layer, or both,
Which comprises a tertiary aryl amine whose highest occupied orbital function (HOMO) value is located between -4.8 eV and -5.8 eV,
organic electroluminescent device.
sequentially forming a hole injection layer, a hole transport layer, and a light emitting auxiliary layer on the first electrode;
forming a light emitting layer on the light emitting auxiliary layer; and
forming a second electrode layer on the light emitting layer;
including,
At least one of the hole injection layer, the hole transport layer, and the light emitting auxiliary layer includes at least one of the compounds represented by Formula 1A of claim 1,
Manufacturing method of organic electroluminescent device.

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