TW202413386A - Heterocyclic compound, organic light-emitting device comprising same, composition for organic material layer of organic light-emitting device comprising same and manufacturing method for organic light-emitting device - Google Patents

Abstract

The present specification provides a heterocyclic compound, an organic light emitting device including the same, a composition for an organic material layer of an organic light emitting device and a method for manufacturing an organic light emitting device.

Description

Heterocyclic compound, organic light-emitting element including the same, organic light-emitting element organic material layer composition, and organic light-emitting element manufacturing method

This application claims priority to and benefits of Korean Patent Application No. 10-2022-0075391 filed on June 21, 2022 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The present invention relates to a heterocyclic compound, an organic light-emitting device comprising the heterocyclic compound, a composition of an organic material layer for an organic light-emitting device, and a method for manufacturing the organic light-emitting device.

Organic electroluminescence (EL) devices are a type of self-emissive display device, and have the advantages of wide viewing angle, excellent contrast and fast response speed.

The organic light-emitting element is composed of a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting element having such a structure, electrons and holes injected from the two electrodes are paired with each other in the organic thin film, and then the paired electrons and holes emit light while annihilating. The organic thin film can be composed of a single layer or multiple layers as needed.

The material used for the organic thin film may have a light-emitting function as required. For example, as the material used for the organic thin film, a compound that can constitute a light-emitting layer by itself can be used, or a compound that can be used as a host or dopant of a light-emitting layer based on a host-dopant can be used. In addition, as the material used for the organic thin film, a compound that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection can also be used.

In order to improve the performance, efficiency and service life of organic light-emitting devices, there is a continuous need to develop materials for organic thin films. [Prior Art Literature] [Patent Literature] U.S. Patent No. 4,356,429

[Technical issues]

The present invention is committed to providing a heterocyclic compound, an organic light-emitting element including the heterocyclic compound, a composition of an organic material layer for an organic light-emitting element, and a method for manufacturing an organic light-emitting element. [Technical Solution]

In an exemplary embodiment of the present application, a heterocyclic compound represented by the following Chemical Formula 1 is provided. [Chemical Formula 1] In Chemical Formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, m1 and m2 are integers from 0 to 3, and when m1 is 2 or more, L1 in the parentheses are the same or different from each other, and when m2 is 2 or more, L2 in the parentheses are the same or different from each other, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, a is an integer from 0 to 3, b and c are each an integer from 0 to 4, and when a is 2 or more, R1 in the brackets are the same or different from each other, and when b is 2 or more, R2 in the brackets are the same or different from each other, and when c is 2 or more, R3 in the brackets are the same or different from each other, and A1 and A2 are the same or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a group represented by the following chemical formula A, [Chemical formula A] In Formula A, Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, is bonded to the position of L1 or L2 of Chemical Formula 1, and at least one of A1 and A2 is a group represented by Chemical Formula A.

In addition, in an exemplary embodiment of the present application, an organic light-emitting element is provided, which includes: a first electrode; a second electrode; and an organic material layer having one or more layers, arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain a heterocyclic compound represented by Chemical Formula 1.

In addition, an exemplary embodiment of the present application provides a composition for an organic material layer of an organic light-emitting element, the composition comprising a heterocyclic compound represented by Chemical Formula 1.

Finally, the exemplary embodiment of the present application provides a method for manufacturing an organic light-emitting element, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer comprises forming the organic material layer having one or more layers by using the composition for the organic material layer according to the present application. [Advantageous Effects]

The heterocyclic compound according to the exemplary embodiment of the present application can be used as a material for an organic material layer of an organic light-emitting element. The heterocyclic compound can be used as a material for a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, and the like in an organic light-emitting element. In particular, the heterocyclic compound represented by Chemical Formula 1 can be used as a material for an electron transport layer or a charge generation layer of an organic light-emitting element.

Specifically, when the heterocyclic compound represented by Chemical Formula 1 is used in an organic light-emitting device, the driving voltage of the device can be reduced, the light efficiency of the device can be improved, and the service life characteristics of the device can be improved due to the thermal stability of the compound.

Hereinafter, this specification will be described in more detail.

In the present specification, when a component “comprises” a constituent element, unless otherwise specifically stated, this does not mean that another constituent element is excluded but means that another constituent element may be further included.

In this specification, the chemical formula Refers to the locations to which the constituent elements are bonded.

In this specification, n of Cn means the number of carbon atoms. That is, for example, C6 to C60 means 6 to 60 carbon atoms.

In the present specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

In the present specification, "substituted or unsubstituted" means unsubstituted or selected from deuterium, halogen, -CN, C1 to C60 alkyl, C2 to C60 alkenyl, C2 to C60 alkynyl, C1 to C60 halogenated alkyl, C1 to C60 alkoxy, C6 to C60 aryloxy, C1 to C60 alkylthiooxy, C6 to C60 arylthiooxy, C1 to C60 alkylsulfonyloxy, C6 to C60 arylsulfonyloxy, C3 to C60 cycloalkyl, C2 to C60 The alkylene group is substituted with one or more substituents selected from the group consisting of C60 heterocycloalkyl, C6 to C60 aryl, C2 to C60 heteroaryl, -SiRR'R", -P(=O)RR' and -NRR', or a substituent to which two or more substituents selected from the exemplified substituents are linked, and R, R' and R'' are each independently a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group and a heteroaryl group.

In this specification, "when no substituent is specified in a chemical formula or a structure of a compound" means that hydrogen atoms are bonded to carbon atoms. However, since deuterium ( ^2H ) is an isotope of hydrogen, some of the hydrogen atoms may be deuterium.

In the exemplary embodiments of the present application, "when no substituent is specified in the chemical formula or the structure of the compound" may mean that all positions accessible to the substituent are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be deuterium as an isotope, and in this case, the deuterium content may be 0% to 100%.

In the exemplary embodiments of the present application, in the case where "a substituent is not specified in the chemical formula or the structure of the compound", for example, when it is not clearly stated that deuterium is excluded and only hydrogen is present (the deuterium content is 0%, the hydrogen content is 100%), hydrogen and deuterium can be mixed and used in the compound.

In the exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen, is an element having a deuteron consisting of one proton and one neutron as a nucleus, and can be represented by hydrogen-2, and the element symbol can also be expressed as D or ^2H .

In the exemplary embodiments of the present application, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A), and isotopes can also be interpreted as elements having the same number of protons but different numbers of neutrons.

In the exemplary embodiment of the present application, when the total number of substituents of the base compound is defined as T1, and the number of specific substituents among the substituents is defined as T2, the content T% of the specific substituent can be defined as T2/T1×100=T%.

That is, in this example, when the total number of substituents that the phenyl group may have is 5 (T1 in the formula) and the number of deuterium in the substituents is 1 (T2 in the formula), The deuterium content of 20% in the phenyl group represented by can be represented by 20%. That is, the deuterium content of 20% in the phenyl group can be represented by the following structural formula.

Furthermore, in the exemplary embodiments of the present application, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not include a deuterium atom (ie, has five hydrogen atoms).

In the present specification, the halogen may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be substituted with another substituent. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, alkenyl includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be substituted with another substituent. The number of carbon atoms of the alkenyl may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples of alkenyl include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, distyryl, styryl and similar groups, but are not limited thereto.

In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be substituted with another substituent. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

In the present specification, a halogenated alkyl group means an alkyl group substituted with a halogen group, and specific examples of the halogenated alkyl group include -CF ₃ , -CF ₂ CF ₃ and the like, but are not limited thereto.

In the present specification, an alkoxy group is represented by -O(R101), and the above-mentioned examples of the alkyl group can be applied to R101.

In the present specification, the aryloxy group is represented by -O(R102), and the above-mentioned examples of the aryl group can be applied to R102.

In the present specification, an alkylthioxy group is represented by -S(R103), and the above-mentioned examples of the alkyl group can be applied to R103.

In the present specification, the arylthiooxy group is represented by -S(R104), and the above-mentioned examples of the aryl group can be applied to R104.

In the present specification, an alkylsulfonic acid oxygen group is represented by -S(=0) ₂ (R105), and the above-mentioned examples of the alkyl group can be applied to R105.

In the present specification, the arylsulfonyloxy group is represented by -S(=0) ₂ (R106), and the above-mentioned examples of the aryl group can be applied to R106.

In the present specification, cycloalkyl includes monocyclic or polycyclic groups having 3 to 60 carbon atoms, and may be substituted with another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly linked or fused to another cyclic group. Here, the other cyclic group may also be a cycloalkyl group, but may also be another cyclic group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

In the present specification, heterocycloalkyl contains O, S, Se, N or Si as a hetero atom, including monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be additionally substituted by another substituent. Here, polycyclic means a group in which the heterocycloalkyl is directly linked or fused to another cyclic group. Here, the other cyclic group may also be a heterocycloalkyl, but may also be another cyclic group, such as a cycloalkyl, an aryl, a heteroaryl and the like. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In this specification, aryl includes monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be substituted with another substituent. Here, polycyclic means a group in which aryl is directly linked or fused to another cyclic group. Here, another cyclic group may also be aryl, but may also be another cyclic group, such as cycloalkyl, heterocycloalkyl, heteroaryl and similar groups. Aryl includes spirocyclic group. The number of carbon atoms of aryl may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, chrysyl, phenanthrenyl, peryl, anthracenyl, terphenylene, phenanthrenyl, pyrenyl, fused tetraphenyl, fused pentaphenyl, fluorenyl, indenyl, acenaphthenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, fused ring groups thereof, and the like, but are not limited thereto.

In the present specification, the terphenyl group can be selected from the following structures.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may bond to each other to form a ring.

When the fluorenyl group is substituted, the substituent may be , , , , , and similar groups, but are not limited thereto.

In the present specification, heteroaryl includes S, O, Se, N or Si as heteroatoms, including monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be substituted by another substituent. Here, polycyclic means a group in which the heteroaryl is directly linked or fused to another cyclic group. Here, the other cyclic group may also be a heteroaryl, but may also be another cyclic group, such as a cycloalkyl, a heterocycloalkyl, an aryl and the like. The number of carbon atoms of the heteroaryl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl, pyrrolyl, pyrimidinyl, oxazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxin group, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazoline group, isoquinazolinyl, quinozoline group, naphthyridinyl, acridinyl, phenanthridine group, group), imidazopyridyl, naphthyl, indanyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazine, dibenzosilylcyclopentadienyl (dibenzosilole group), spirobis(dibenzosilylcyclopentadiene), dihydrophenazinyl, phenanthridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, dihydroindolyl, 10,11-dihydro-dibenzo[b,f]azepine, 9,10-dihydroacridinyl, phenazinyl, phenothiazine group), phthalazinyl, phenanthroline, naphthobenzofuranyl, naphthobenzothiophene, benzo[c][1,2,5]thiadiazolyl, 2,3-dihydrobenzo[b]thiophene, 2,3-dihydrobenzofuranyl, 5,10-dihydrodibenzo[b,e][1,4]azosilalinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindolyl, 5,11-dihydroindeno[1,2-b]carbazolyl and the like, but are not limited thereto.

In the present specification, when a substituent is a carbazolyl group, it means bonded to the nitrogen or carbon of carbazole.

In the present specification, when the carbazole group is substituted, the other substituent may be substituted on the nitrogen or carbon of the carbazole.

In the present specification, the benzocarbazolyl group may be any of the following structures.

In the present specification, the dibenzocarbazolyl group may be any of the following structures.

In the present specification, the naphthobenzofuranyl group may be any of the following structures.

In the present specification, the naphthobenzothienyl group may be any of the following structures.

In the present specification, the silyl group includes Si and is a substituent to which the Si atom is directly linked as a free radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same as or different from each other, and may each independently be a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. Specific examples of the silyl group include (Trimethylsilyl), (Triethylsilyl), (tert-butyldimethylsilyl), (vinyldimethylsilyl), (propyldimethylsilyl), (Triphenylsilyl), (diphenylsilyl), (phenylsilyl) and similar groups, but are not limited thereto.

In the present specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same or different from each other, and can each independently be a substituent consisting of at least one of hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl. Specifically, the phosphine oxide group can be substituted by an alkyl or aryl group, and the above examples can be applied to alkyl and aryl groups. Examples of the phosphine oxide group include dimethylphosphine oxide, diphenylphosphine oxide, dinaphthylphosphine oxide and similar groups, but are not limited thereto.

In the present specification, an amine group is represented by -N(R112)(R113), and R112 and R113 are the same or different and may be independently a substituent consisting of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and a heteroaryl group. The amine group may be selected from the group consisting of -NH ₂ , a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenylterphenylamino, biphenylterphenylamino and the like, but are not limited thereto.

In the present specification, the above-mentioned examples of the aryl group can be applied to arylene groups other than divalent arylene groups.

In the present specification, the above-mentioned examples of the heteroaryl group can be applied to heteroaryl groups other than the divalent heteroaryl group.

In the present specification, an "adjacent" group may mean a substituent substituted with an atom directly linked to the atom in which the corresponding substituent is substituted, a substituent that is spatially located closest to the corresponding substituent, or another substituent substituted with an atom in which the corresponding substituent is substituted. For example, two substituents substituted at adjacent positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

The hydrocarbon ring and heterocyclic ring that adjacent groups can form include an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocyclic ring, and an aromatic heterocyclic ring, and the structures exemplified by the above-mentioned cycloalkyl group, aryl group, heterocycloalkyl group, and heteroaryl group can be applied to rings other than the ring that is not a monovalent group.

In an exemplary embodiment of the present application, a heterocyclic compound represented by Chemical Formula 1 is provided.

The heterocyclic compound represented by Chemical Formula 1 is a compound including a phosphine oxide group and a phenanthroline group, and can efficiently transfer electrons due to stable bonding with a metal used for a negative electrode. Thus, when the heterocyclic compound represented by Chemical Formula 1 is used in an organic light-emitting element, an organic light-emitting element having excellent drive, efficiency, and service life can be manufactured.

In the exemplary embodiments of the present application, a group not represented by a substituent or a group represented by hydrogen may mean that all may be substituted with deuterium. That is, it may indicate that hydrogen or deuterium may be substituted with each other.

In the exemplary embodiment of the present application, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% to 100%.

In the exemplary embodiment of the present application, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 10% to 100%.

In the exemplary embodiment of the present application, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 20% to 100%.

In general, compounds bonded to hydrogen and compounds substituted with deuterium show differences in their thermodynamic behavior. The reason for this is that the mass of a deuterium atom is twice as high as that of hydrogen, but due to the difference in atomic mass, deuterium is characterized by having an even lower vibration energy. In addition, the bond length of carbon to deuterium is shorter than that to hydrogen, and the dissociation energy for breaking the bond is also stronger than that to hydrogen. This is due to the fact that the van der Waals radius of deuterium is smaller than that of hydrogen, and therefore the extension of the bond between carbon and deuterium becomes even narrower.

The deuterium-substituted compound in the heterocyclic compound represented by Chemical Formula 1 of the present invention is characterized in that the ground state energy is lower than the ground state energy of the hydrogen-substituted compound, and the shorter the bond length between carbon and deuterium, the smaller the molecular hardcore volume. Therefore, the electrical polarizability can be reduced, and the intermolecular interaction can be weakened, so that the volume of the device film can be increased. These characteristics cause the effect of reducing the crystallinity by generating an amorphous state of the film. Therefore, the deuterium-substituted compound in the heterocyclic compound represented by Chemical Formula 1 can effectively improve the heat resistance of the organic light emitting diode (OLED) device, thereby improving the service life and driving characteristics.

In this specification, "OLED device" may be expressed by terms such as "organic light emitting diode", "organic light emitting diode (OLED)", "organic light emitting element" and "organic electroluminescent element".

In the exemplary embodiments of the present application, L1 and L2 of Chemical Formula 1 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, m1 and m2 are integers from 0 to 3, and when m1 is 2 or more, the L1s in the brackets are the same as or different from each other, and when m2 is 2 or more, the L2s in the brackets are the same as or different from each other.

In the exemplary embodiments of the present application, L1 and L2 are the same as or different from each other, and can each independently be a direct bond; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In the exemplary embodiments of the present application, L1 and L2 are the same as or different from each other, and can each independently be a direct bond; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

In the exemplary embodiments of the present application, L1 and L2 are the same as or different from each other, and can each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

In the exemplary embodiments of the present application, L1 and L2 are the same as or different from each other, and can each independently be a direct bond; a phenylene group; or a biphenylene group.

In the exemplary embodiment of this application, L1 is a direct key.

In the exemplary embodiments of the present application, L1 is a phenylene group which is unsubstituted or substituted with one or more deuterium groups.

In the exemplary embodiments of the present application, L1 is a biphenylene group which is unsubstituted or substituted with one or more deuterium groups.

In the exemplary embodiment of this application, L2 is a direct key.

In the exemplary embodiments of the present application, L2 is a phenylene group which is unsubstituted or substituted with one or more deuterium groups.

In the exemplary embodiments of the present application, L2 is a biphenylene group which is unsubstituted or substituted with one or more deuterium groups.

In the exemplary embodiment of the present application, m1 is 0. In the exemplary embodiment of the present application, m1 is 1. In the exemplary embodiment of the present application, m1 is 2. In the exemplary embodiment of the present application, m1 is 3. In addition, when m1 is 2 or higher, L1 in the parentheses are the same or different from each other.

In the exemplary embodiment of the present application, m2 is 0. In the exemplary embodiment of the present application, m2 is 1. In the exemplary embodiment of the present application, m2 is 2. In the exemplary embodiment of the present application, m2 is 3. In addition, when m2 is 2 or higher, L2 in the brackets are the same or different from each other.

In the exemplary embodiments of the present application, R1 to R3 of Chemical Formula 1 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, a is an integer from 0 to 3, b and c are each an integer from 0 to 4, and when a is 2 or more, the R1 in the brackets are the same as or different from each other, and when b is 2 or more, the R2 in the brackets are the same as or different from each other, and when c is 2 or more, the R3 in the brackets may be the same as or different from each other.

In the exemplary embodiments of the present application, R1 to R3 are the same as or different from each other, and may be each independently hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In the exemplary embodiments of the present application, R1 to R3 are the same as or different from each other, and may be each independently hydrogen; deuterium; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In the exemplary embodiments of the present application, R1 to R3 are the same as or different from each other, and may be each independently hydrogen; deuterium; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

In the exemplary embodiment of the present application, R1 to R3 are the same as or different from each other, and may each independently be hydrogen or deuterium.

In the exemplary embodiment of the present application, a is 0. In the exemplary embodiment of the present application, a is 1. In the exemplary embodiment of the present application, a is 2. In the exemplary embodiment of the present application, a is 3. When a is 2 or more, R1 in the brackets are the same or different from each other.

In the exemplary embodiment of the present application, b is 0. In the exemplary embodiment of the present application, b is 1. In the exemplary embodiment of the present application, b is 2. In the exemplary embodiment of the present application, b is 3. In the exemplary embodiment of the present application, b is 4. When b is 2 or higher, R2 in the brackets are the same or different from each other.

In the exemplary embodiment of the present application, c is 0. In the exemplary embodiment of the present application, c is 1. In the exemplary embodiment of the present application, c is 2. In the exemplary embodiment of the present application, c is 3. In the exemplary embodiment of the present application, c is 4. When c is 2 or higher, R3 in the brackets are the same or different from each other.

In the exemplary embodiments of the present application, A1 and A2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a group represented by the following chemical formula A, and at least one of A1 and A2 may be a group represented by the following chemical formula A. [Chemical Formula A]

In Formula A, Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and It is the position bonded to L1 or L2 of Chemical Formula 1.

In the exemplary embodiments of the present application, A1 and A2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a group represented by chemical formula A, and at least one of A1 and A2 may be a group represented by chemical formula A.

In the exemplary embodiments of the present application, A1 and A2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or a group represented by chemical formula A, and at least one of A1 and A2 may be a group represented by chemical formula A.

In the exemplary embodiments of the present application, A1 and A2 are the same or different from each other, and can each independently be a group represented by the following chemical formula B; or a group represented by chemical formula A. [Chemical Formula B]

In Formula B, R4 and R5 are the same or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 in the parentheses are the same or different from each other, and when e is 2 or greater, R5 in the parentheses are the same or different from each other, and It is the position bonded to L1 or L2 of Chemical Formula 1.

Even in this case, at least one of A1 and A2 may be a group represented by the chemical formula A.

In the exemplary embodiments of the present application, Ar1 and Ar2 in Chemical Formula A are the same as or different from each other, and can each independently be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In the exemplary embodiments of the present application, Ar1 and Ar2 are the same as or different from each other, and can be each independently a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In the exemplary embodiments of the present application, Ar1 and Ar2 are the same as or different from each other, and can be each independently a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

In the exemplary embodiments of the present application, Ar1 and Ar2 are the same as or different from each other, and can be each independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted pyridyl group.

In the exemplary embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and can be each independently a phenyl group which is unsubstituted or substituted with one or more deuterium groups; or a pyridyl group which is unsubstituted or substituted with one or more deuterium groups.

In the exemplary embodiment of the present application, Ar1 and Ar2 are identical to each other.

In the exemplary embodiments of the present application, R4 and R5 in Chemical Formula B are the same as or different from each other, and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 in the brackets are the same as or different from each other, and when e is 2 or greater, R5 in the brackets may be the same as or different from each other.

In the exemplary embodiments of the present application, R4 and R5 are the same as or different from each other, and can be each independently hydrogen; deuterium; substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl.

In the exemplary embodiments of the present application, R4 and R5 are the same as or different from each other, and can be each independently hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In the exemplary embodiments of the present application, R4 and R5 are the same as or different from each other, and can be each independently hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted pyridyl.

In the exemplary embodiments of the present application, R4 and R5 are the same as or different from each other and can be independently hydrogen; deuterium; phenyl which is unsubstituted or substituted with one or more deuteriums; naphthyl which is unsubstituted or substituted with one or more deuteriums; or pyridyl which is unsubstituted or substituted with one or more deuteriums.

In the exemplary embodiment of the present application, d is 0. In the exemplary embodiment of the present application, d is 1. In the exemplary embodiment of the present application, d is 2. When d is 2, R4 in the brackets are the same or different from each other.

In the exemplary embodiment of the present application, e is 0. In the exemplary embodiment of the present application, e is 1. In the exemplary embodiment of the present application, e is 2. In the exemplary embodiment of the present application, e is 3. In the exemplary embodiment of the present application, e is 4. In the exemplary embodiment of the present application, e is 5. When e is 2 or higher, R5 in the brackets are the same or different from each other.

In the exemplary embodiment of the present application, Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or Chemical Formula 1-2. [Chemical Formula 1-1] [Chemical formula 1-2]

In Chemical Formula 1-1 and Chemical Formula 1-2, L1, L2, Ar1, Ar2, R1 to R3, m1, m2 and a to e are defined the same as in Chemical Formula 1, R4 and R5 are the same or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 in the brackets are the same or different from each other, and when e is 2 or greater than 2, R5 in the brackets are the same or different from each other.

In the exemplary embodiment of the present application, Chemical Formula 1-1 can be represented by the following Chemical Formulas 1-1-1 to 1-1-3. [Chemical Formula 1-1-1] [Chemical formula 1-1-2] [Chemical formula 1-1-3]

In Chemical Formula 1-1-1 to Chemical Formula 1-1-3, L1, L2, Ar1, Ar2, R1 to R5, m1, m2, and a to e have the same definitions as those in Chemical Formula 1-1.

In the exemplary embodiment of the present application, Chemical Formula 1-2 may be represented by any one of the following Chemical Formulas 1-2-1 to 1-2-3. [Chemical Formula 1-2-1] [Chemical formula 1-2-2] [Chemical formula 1-2-3]

In Chemical Formula 1-2-1 to Chemical Formula 1-2-3, L1, L2, Ar1, Ar2, R1 to R5, m1, m2, and a to e have the same definitions as those in Chemical Formula 1-2.

In the exemplary embodiments of the present application, Chemical Formula 1 may be represented by any one of the following compounds.

In addition, various substituents may be introduced into the structure of Chemical Formula 1 to synthesize a compound having the inherent characteristics of the introduced substituents. For example, substituents commonly used in hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials used when manufacturing an organic light-emitting element may be introduced into the core structure to synthesize a material that meets the required conditions for each organic material layer.

In addition, the compound of Chemical Formula 1 has excellent thermal stability, and such thermal stability provides driving stability for the organic light-emitting element and improves the service life characteristics.

In an exemplary embodiment of the present application, an organic light-emitting element is provided, comprising: a first electrode; a second electrode; and an organic material layer having one or more layers, disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain a heterocyclic compound represented by Chemical Formula 1.

In another exemplary embodiment, an organic light emitting element is provided, in which the organic material layer includes an electron transport layer, and the electron transport layer includes a heterocyclic compound represented by Chemical Formula 1.

In an exemplary embodiment of the present application, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

In another exemplary embodiment, the first electrode may be a negative electrode and the second electrode may be a positive electrode.

The organic light-emitting device of the present invention may further include one layer or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

1 to 3 illustrate the stacking sequence of the electrode and the organic material layer of the organic light emitting device according to the exemplary embodiment of the present application. However, the scope of the present application is not intended to be limited by these figures, and the structure of the organic light emitting device known in the art can also be applied to the present application.

1 , an organic light emitting device is shown in which a positive electrode 200, an organic material layer 300, and a negative electrode 400 are sequentially stacked on a substrate 100. However, the organic light emitting device is not limited to this structure, and as in FIG. 2 , an organic light emitting device in which a negative electrode, an organic material layer, and a positive electrode are sequentially stacked on a substrate may also be implemented.

FIG3 exemplifies the case where the organic material layer is multi-layered. The organic light-emitting element according to FIG3 includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to the stacking structure described above, and as needed, other layers except the light-emitting layer may be omitted, and another necessary functional layer may be further added.

In addition, the organic light-emitting element according to the exemplary embodiment of the present application includes: a first electrode; a first stack disposed on the first electrode and including a first light-emitting layer; a charge generating layer disposed on the first stack; a second stack disposed on the charge generating layer and including a second light-emitting layer; and a second electrode disposed on the second stack.

In this case, the charge generation layer may include the heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound is used in the charge generation layer, the driving, efficiency, and life of the organic light emitting device may become excellent.

In an exemplary embodiment of the present application, the charge generation layer may be an N-type charge generation layer.

When the heterocyclic compound represented by Chemical Formula 1 is used as an N-type charge generation layer, a gap state is formed in the N-type charge generation layer, and electrons generated from the P-type charge generation layer are injected into the electron transport layer through the gap state generated in the N-type charge generation layer, so that a stable gap state is formed by a stable bond between the material and the metal, and thus, the electron transfer efficiency from the P-type charge generation layer to the N-type charge generation layer is improved. Thereby, the following effects are achieved: the driving voltage of the organic light-emitting element is reduced and the efficiency and service life of the element are improved.

In addition, the first stack and the second stack may each independently further include one or more of the above-mentioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer and the like.

As an organic light emitting element according to an exemplary embodiment of the present application, an organic light emitting element having a two-stacked series structure is exemplarily shown in the following FIG. 4 .

In this case, the first electron blocking layer, the first hole blocking layer, the second hole blocking layer, and the like described below in FIG. 4 may be omitted depending on the circumstances.

In an exemplary embodiment of the present application, a composition for an organic material layer of an organic light-emitting element is provided, the composition including a heterocyclic compound represented by Chemical Formula 1.

The composition may be used when forming an organic material layer of an organic light-emitting device, and specifically, the composition may be preferably used as a material of an electron transport layer or a charge generation layer.

The composition is in the form of a simple mixture of two or more compounds, and materials in a powder state may be mixed before forming the organic material layer of the organic light-emitting element, and compounds in a liquid state may be mixed at a temperature equal to or greater than the appropriate temperature. The composition is in a solid state at a temperature equal to or less than the melting point of each material, and can be maintained in a liquid phase when the temperature is adjusted.

The composition may further include materials known in the art, such as solvents and additives.

In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting element is provided, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer comprises forming the organic material layer having one or more layers by using a composition for an organic material layer according to an exemplary embodiment of the present application.

In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, wherein an organic material layer is formed by forming a heterocyclic compound represented by Chemical Formula 1 using a thermal vacuum deposition method.

In addition to the above-mentioned compounds being used to form the organic material layer, the organic light-emitting device according to the exemplary embodiment of the present application can be manufactured by a typical manufacturing method and material of the organic light-emitting device.

The organic light-emitting device of the present invention may further include one layer or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole auxiliary layer and a hole blocking layer.

In the exemplary embodiment of the present application, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound according to Chemical Formula 1 may be used as a material for the blue organic light-emitting element.

In the exemplary embodiment of the present application, the organic light emitting element may be a green organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light emitting element.

In the exemplary embodiment of the present application, the organic light emitting element may be a red organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light emitting element.

When manufacturing an organic light-emitting element, the heterocyclic compound can be formed as an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.

The organic material layer of the organic light-emitting element of the present invention may be composed of a single-layer structure, but may also be composed of a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as the organic material layer. However, the structure of the organic light-emitting element is not limited thereto, but may include a smaller number of organic material layers.

In the exemplary embodiment of the present application, the organic material layer may contain an iridium-based dopant.

In the exemplary embodiment of the present application, as the iridium series dopant, Ir(ppy) ₃ which is a green phosphorescent dopant can be used.

In the exemplary embodiment of the present application, as the iridium-based dopant, (piq) ₂ (Ir) _(acac) which is a red phosphorescent dopant can be used.

In addition to the above-mentioned heterocyclic compound being used to form an organic material layer having one or more layers, the organic light emitting device of the present invention can be manufactured using typical manufacturing methods and materials of an organic light emitting device.

In the organic light-emitting device of the present application, as the positive electrode material, a material having a relatively high work function can be used, and a transparent conductive oxide, metal or conductive polymer and the like can be used. Specific examples of the positive electrode material include: metals, such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO ₂ :Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.

As the negative electrode material, a material having a relatively low work function may be used, and metals, metal oxides, or conductive polymers and the like may be used. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF/Al or LiO ₂ /Al; and the like, but are not limited thereto.

As the hole injection material, a known hole injection material may be used, and for example, a phthalocyanine compound, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or a phthalocyanine compound disclosed in [Advanced Materials (Advanced Materials (Advanced Materials (Advanced Materials (Advanced Materials (Advanced Materials (Advanced Materials (Advanced Materials (Advanced Materials (Advanced Materials (Advanced Materials Star-shaped burst-type amine derivatives described in [Journal of Materials], 6, p. 677 (1994), such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4''-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (which is a soluble conductive polymer), polyaniline/camphorsulfonic acid or polyaniline/poly(4-styrenesulfonate), and similar materials.

As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like can be used, and low molecular weight materials or polymer materials can also be used.

As electron transport materials, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, dibenzoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, and similar materials can be used, and low molecular weight materials and polymer materials can also be used.

As the electron injection material, for example, LiF is typically used in this technology, but the present application is not limited thereto.

As the light-emitting material, a red, green or blue light-emitting material can be used, and two or more light-emitting materials can be mixed and used as needed. In this case, two or more light-emitting materials are deposited as or used as separate supply sources, or are pre-mixed to be deposited as and used as one supply source. In addition, a fluorescent material can also be used as the light-emitting material, but a phosphorescent material can also be used. As the light-emitting material, a material that emits light by combining holes and electrons injected from the positive electrode and the negative electrode can also be used alone, but a material in which a host material and a dopant material participate in light emission together can also be used.

When the host of the light-emitting material is mixed and used, the host of the same series can be mixed and used, and the host of different series can be mixed and used. For example, two or more types of materials selected from n-type host materials or p-type host materials can be used as the host material of the light-emitting layer.

Depending on the materials to be used, the organic light emitting device according to the exemplary embodiment of the present application may be a top emission type, a bottom emission type, or a dual emission type.

The heterocyclic compound according to the exemplary embodiment of the present application may even function in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like based on principles similar to those applied to organic light-emitting devices.

Hereinafter, this specification will be explained in more detail by examples, but these examples are provided only to illustrate this application and are not intended to limit the scope of this application. <Examples> [ Preparation Example 1] Preparation of Compound 1 1 ) Preparation of Compound 1-1

Compound 3-bromo-[1,1'-biphenyl]-2-amine (A) (40 g, 0.161 mol, 1 equivalent), dichloromethane (hereinafter referred to as DCM) (510 ml) and triethylamine (Et ₃ N) (16.3 g, 0.161 mol, 1 equivalent) were placed in a reaction flask, and the resulting mixture was cooled and stirred at 0° C. Thereafter, 2-chlorobenzyl chloride (B) (31.0 g, 0.177 mol, 1.1 equivalent) was diluted in DCM (90 ml) and slowly added to DCM, and the resulting mixture was stirred at room temperature for 1 hour (h). After the reaction was terminated by adding water, extraction was performed using DCM and water. Thereafter, water was removed using MgSO ₄ . The residue was separated by silica gel column to obtain 50.6 g of compound 1-1 with a yield of 81%. 2 ) Preparation of compound 1-2

Compound 1-1 (50 g, 0.129 mol, 1 eq.), nitrobenzene (500 ml), triphenylphosphine (33.0 g, 0.126 mol, 2.0 eq.) and phosphonyl chloride (29.0 g, 0.189 mol, 1.5 eq.) were placed in a reaction flask, and the resulting mixture was stirred at 150° C. for 3 hours (h). After the reaction was completed, the mixture was cooled to room temperature, and an aqueous NaHCO ₃ solution was added to adjust the pH to 7. The formed crystals were filtered and then washed with pure water. Thereafter, the filtered crystals were slurried under DCM/acetone conditions, filtered, washed with acetone, and then dried to obtain 37.6 g of compound 1-2 with a yield of 79%. 3 ) Preparation of Compound 1-3

Compound 1-2 (35 g, 0.095 mol, 1 eq.), diphenylphosphine oxide (C) (21.2 g, 0.105 mol, 1.1 eq.), Pd(PPh ₃ ) ₄ (5.8 g, 0.005 mol, 0.05 eq.), Et ₃ N (19.2 g, 0.190 mol, 2.0 eq.) and toluene (350 ml) were placed in a reaction flask, and the resulting mixture was stirred at 110° C. for 3 hours (h). After the reaction was terminated by adding water, extraction was performed using DCM and water. Thereafter, water was removed using MgSO _4. The residue was separated by a silica gel column to obtain 25.0 g of compound 1-3 with a yield of 54%. 4 ) Preparation of compound 1-4

1,4-Dioxane (250 mL) was added to compound 1-3 (25 g, 0.051 mol, 1 eq), B ₂ pin ₂ (19.6 g, 0.077 mol, 1.5 eq), Pd(dba) ₂ (2.9 g, 0.005 mol, 0.1 eq), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) (4.8 g, 0.010 mol, 0.2 eq) and KOAc (15.0 g, 0.153 mol, 3.0 eq) in a reaction flask, and the resulting mixture was stirred under reflux for 3 hours (h). When the reaction was completed, the mixture was cooled to room temperature, the solvent was removed, and the residue was slurried under DCM/isopropyl ether conditions. Thereafter, the obtained slurry was filtered, washed with isopropyl ether and water, and then dried to obtain 27 g of compound 1-4 with a yield of 94%. 5 ) Preparation of compound 1

Compound 1-4 (10 g, 0.017 mol, 1 eq.), 2-bromo-1,10-phenanthroline (D) (4.4 g, 0.017 mol, 1.0 eq.), Pd(PPh ₃ ) ₄ (1.2 g, 0.001 mol, 0.05 eq.), K ₃ PO ₄ (7.9 g, 0.037 mol, 2.2 eq.), 1,4-dioxane (120 ml) and water (30 ml) were placed in a reaction flask, and the resulting mixture was stirred under reflux for 3 hours (h). When the reaction was completed, the mixture was cooled to room temperature, and then crystallized by adding water to the mixture. The crystals were filtered and washed with methanol and water. After that, the washed crystals were filtered using silica gel to obtain 8.2 g of compound 1 with a yield of 79%.

The compounds in Table 1 below were synthesized in the same manner as in Preparation Example 1, except that in Preparation Example 1, intermediate A in Table 1 below was used instead of 3-bromo-[1,1'-biphenyl]-2-amine (A), intermediate B in Table 1 below was used instead of 2-chlorobenzyl chloride (B), intermediate C in Table 1 below was used instead of diphenylphosphine oxide (C), and intermediate D in Table 1 below was used instead of 2-bromo-1,10-phenanthroline (D). [Table 1] Compound No. Intermediate A Intermediate B Intermediate C Intermediate D Yield 1 26% 2 28% 18 38% twenty four 26% 35 26% 50 37% 64 50% 68 52% 78 40% 100 50% 101 54% 113 52% 127 45% 133 28% 135 27% 186 36% 188 51% 189 50% 197 47% 233 50% 238 47% 265 48% 268 51% 270 49% 272 49% [ Preparation Example 2] Preparation of Compound 92 1 ) Preparation of compound 92-1

Compound 92-1 was synthesized in the same manner as in the preparation of compound 1-1 in Preparation Example 1, except that 4-chlorobenzyl chloride was used instead of 2-chlorobenzyl chloride (B). 2 ) Preparation of compound 92-2

Compound 92-2 was synthesized in the same manner as in the preparation of compound 1-2 in Preparation Example 1, except that compound 92-1 was used instead of compound 1-1. 3 ) Preparation of compound 92-3

Compound 92-2 (20 g, 0.054 mol, 1 eq), diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (C) (21.8 g, 0.054 mol, 1.0 eq), Pd(PPh ₃ ) ₄ (3.5 g, 0.003 mol, 0.05 eq), K ₃ PO ₄ (25.3 g, 0.119 mol, 2.2 eq), 1,4-dioxane (240 ml) and water (60 ml) were placed in a reaction flask, and the resulting mixture was stirred under reflux for 3 hours (h). After the reaction was terminated by adding water, extraction was performed using DCM and water. Thereafter, water was removed using MgSO ₄ . The residue was separated by silica gel column to obtain 25.5 g of compound 92-3 with a yield of 83%. 4 ) Preparation of compound 92-4

Compound 92-4 was synthesized in the same manner as in the preparation of Compound 1-4 in Preparation Example 1, except that Compound 92-3 was used instead of Compound 1-3. 5 ) Preparation of Compound 92

Compound 92 was synthesized in the same manner as in the preparation of Compound 1 in Preparation Example 1, except that Compound 92-4 was used instead of Compound 1-4.

The compounds in Table 2 below were synthesized in the same manner as in Preparation Example 2, except that in Preparation Example 2, intermediate A in Table 2 below was used instead of 3-bromo-[1,1'-biphenyl]-2-amine (A), intermediate B in Table 2 below was used instead of 2-chlorobenzyl chloride (B), intermediate C in Table 2 below was used instead of diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (C), and intermediate D in Table 2 below was used instead of 2-bromo-1,10-phenanthroline (D). [Table 2] Compound No. Intermediate A Intermediate B Intermediate C Intermediate D Yield 92 71% 93 65% 257 66% [ Preparation Example 3] Preparation of Compound 145 1 ) Preparation of compound 145-1

Compound 145-1 was synthesized in the same manner as in the preparation of compound 1-1 of Preparation Example 1, except that 4-chloro-[1,1'-biphenylyl]-2-amine was used instead of 3-bromo-[1,1'-biphenylyl]-2-amine (A) and 2-bromobenzyl chloride was used instead of 2-chlorobenzyl chloride (B). 2 ) Preparation of compound 145-2

Compound 145-2 was synthesized in the same manner as in the preparation of compound 1-2 in Preparation Example 1, except that compound 145-1 was used instead of compound 1-1. 3 ) Preparation of compound 145-3

Compound 145-3 was synthesized in the same manner as in the preparation of compound 1-3 of Preparation Example 1, except that compound 145-2 was used instead of compound 1-1. 4 ) Preparation of compound 145-4

Compound 145-4 was synthesized in the same manner as in the preparation of compound 1-4 in Preparation Example 1, except that compound 145-3 was used instead of compound 1-3. 5 ) Preparation of compound 145

Compound 145 was synthesized in the same manner as in the preparation of Compound 1 of Preparation Example 1, except that Compound 145-4 was used instead of Compound 1-4 and 2-bromo-9-phenyl-1,10-phenanthroline was used instead of 2-bromo-1,10-phenanthroline (D).

The compounds in Table 3 below were synthesized in the same manner as in Preparation Example 3, except that Intermediate A in Table 3 below was used instead of 4-chloro-[1,1'-biphenyl]-2-amine (A), Intermediate B in Table 3 below was used instead of 2-bromobenzyl chloride (B), Intermediate C in Table 3 below was used instead of diphenylphosphine oxide (C), and Intermediate D in Table 3 below was used instead of 2-bromo-9-phenyl-1,10-phenanthroline (D). [Table 3] Compound No. Intermediate A Intermediate B Intermediate C Intermediate D Yield 145 35% 160 37% 171 35% 200 42% 219 40% 227 40% 248 43%

The compound was prepared in the same manner as in the preparation example, and the synthesis confirmation results are shown in Table 4 and Table 4. Table 4 shows the measurement values of ¹ H nuclear magnetic resonance (NMR) (CDCl ₃ , 200 Mz), and Table 5 shows the measurement values of field desorption mass spectrometry (FD-MS). [Table 4] Compound ¹ H NMR (CDCl ₃ , 200Mz) 1 δ = 8.80 (1H, d), 8.71 (1H, d), 8.45-8.43 (2H, m), 8.35-8.33 (2H, m), 8.20-8.16 (2H, m), 7.99 (1H, d), 7.90-7.83 (3H, m), 7.77-7.60 (8H, m), 7.56-7.51 (7H, m), 7.29 (1H, d) 2 δ = 8.71-8.68 (2H, m), 8.45 (1H, s), 8.35-8.33 (4H, m), 8.20-8.16 (2H, m), 7.99 (1H, d), 7.90-7.83 (3H, m), 7.77-7.60 (8H, m), 7.55-7.49 (9H, m), 7.29-7.26 (2H, m) 18 δ = 9.63 (1H, s), 8.81 (1H, d), 8.71-8.65 (3H, m), 8.56 (1H, s), 8.40-8.35 (3H, m), 8.20 (1H, d), 7.99-7.97 (2H, m), 7.90-7.83 (2H, m), 7.77-7.60 (9H, m), 7.57-7.51 (7H, m), 7.29 (1H, d) twenty four δ = 8.71-8.68 (2H, m), 8.35-8.16 (8H, m), 7.99 (1H, d), 7.90-7.83 (2H, m), 7.77-7.60 (8H, m), 7.55-7.49 (9H, m), 7.29-7.26 (2H, m) 35 δ = 8.71-8.68 (2H, m), 8.35-8.30 (4H, m), 8.20-8.18 (2H, m), 8.08 (1H, t), 7.99-7.83 (4H, m), 7.77-7.60 (8H, m), 7.55-7.49 (9H, m), 7.29-7.26 (2H, m) 50 δ = 9.18 (1H, d), 8.72-8.70 (2H, m), 8.55 (1H, d), 8.45-8.33 (5H, m), 8.20-8.16 (2H, m), 7.99 (1H, d), 7.90-7.83 (3H, m), 7.77-7.61 (8H, m), 7.53-7.51 (6H, m), 7.29-7.23 (2H, m) 64 δ = 8.80 (1H, d), 8.72-8.70 (2H, m), 8.62-8.56 (5H, m), 8.45-8.33 (4H, m), 8.20 (1H, d), 7.99-7.83 (8H, m), 7.73-7.56 (4H, m), 7.29 (1H, d) 68 δ = 8.72-8.69 (3H, m), 8.33-8.16 (8H, m), 7.99 (1H, d), 7.90 (1H, d), 7.83 (1H, d), 7.77-7.61 (7H, m), 7.55-7.49 (9H, m), 7.29-7.27 (2H, m) 78 δ = 8.80 (1H, d), 8.72-8.70 (2H, m), 8.45 (1H, d), 8.33-8.31 (2H, m), 8.20-8.18 (2H, m), 8.08 (1H, t), 7.99-7.83 (4H, m), 7.77-7.68 (6H, m), 7.61-7.51 (8H, m), 7.29 (1H, d) 92 δ = 8.80 (1H, d), 8.71-8.64 (5H, m), 8.45 (1H, d), 8.20-8.14 (2H, m), 7.99-7.94 (6H, m), 7.90-7.83 (2H, m), 7.77-7.68 (5H, m), 7.65-7.51 (9H, m), 7.29 (1H, d) 93 δ = 8.80 (1H, d), 8.71-8.67 (5H, m), 8.45 (1H, d), 8.20-8.12 (3H, m), 7.99-7.97 (2H, m), 7.90-7.83 (3H, m), 7.77-7.68 (7H, m), 7.65-7.51 (9H, m), 7.29 (1H, d) 100 δ = 8.80 (1H, d), 8.71-8.66 (5H, m), 8.56 (1H, s), 8.45-8.40 (2H, m), 8.20 (1H, d), 7.99-7.97 (2H, m), 7.90-7.83 (2H, m), 7.77-7.68 (5H, m), 7.61-7.51 (8H, m), 7.29 (1H, d) 101 δ = 8.71-8.66 (6H, m), 8.56 (1H, s), 8.40-8.33 (3H, m), 8.20 (1H, d), 7.99-7.83 (4H, m), 7.77-7.61 (6H, m), 7.55-7.49 (9H, m), 7.29-7.27 (2H, m) 113 δ = 8.85 (1H, s), 8.71-8.68 (6H, m), 8.37 (1H, d), 8.27-8.16 (4H, m), 8.06-7.99 (4H, m), 7.90-7.83 (2H, m), 7.77-7.61 (7H, m), 7.59-7.51 (7H, m), 7.29-7.27 (2H, m) 127 δ = 9.18 (1H, d), 8.71-8.68 (5H, m), 8.55 (1H, d), 8.41-8.37 (2H, m), 8.20-8.18 (2H, m), 8.08 (1H, t), 7.99-7.83 (4H, m), 7.77-7.68 (6H, m), 7.61-7.51 (7H, m), 7.29-7.23 (2H, m) 133 δ = 9.04(1H, d), 8.80(1H, d), 8.71(1H, d), 8.45(1H, d), 8.36-8.30(2H, m), 8.20(1H, d), 7.99-7.95(2H, m), 7.90-7.83(3H, m), 7.77-7.75(5H, m), 7.68-7.61(3H, m), 7.56-7.51(7H, m), 7.29(1H, d) 135 δ = 9.04 (1H, d), 8.85 (1H, s), 8.71-8.68 (2H, m), 8.37-8.30 (3H, m), 8.20 (1H, d), 8.06-7.90 (6H, m), 7.88-7.83 (2H, m), 7.77-7.74 (5H, m), 7.68-7.61 (4H, m), 7.59-7.51 (7H, m), 7.29-7.27 (2H, m) 145 δ = 8.76-8.71(3H, m), 8.63(1H, d), 8.39-8.33(4H, m), 8.20(1H, d), 7.99-7.83(4H, m), 7.77-7.68(6H, m), 7.61-7.55(4H, m), 7.51-7.47(7H, m), 7.29-7.27(2H, m) 160 δ = 9.18 (1H, d), 8.82 (1H, d), 8.71 (1H, d), 8.55 (1H, d), 8.47-8.36 (4H, m), 8.25-8.20 (2H, m), 7.99-7.83 (4H, m), 7.77-7.68 (7H, m), 7.61-7.51 (8H, m), 7.29-7.23 (2H, m) 171 δ = 9.18 (1H, d), 8.71 (1H, d), 8.63 (1H, d), 8.55 (1H, d), 8.41-8.36 (3H, m), 8.20 (1H, d), 8.10-7.83 (6H, m), 7.77-7.68 (7H, m), 7.61-7.51 (8H, m), 7.29-7.23 (2H, m) 186 δ = 9.12-9.04 (3H, m), 8.80-8.71 (4H, m), 8.52-8.45 (3H, m), 8.30-8.20 (4H, m), 7.99 (1H, d), 7.90-7.83 (4H, m), 7.74 (1H, t), 7.68-7.54 (5H, m), 7.29 (1H, d) 188 δ = 8.80-8.71(3H, m), 8.63(1H, d), 8.55-8.39(4H, m), 8.20(1H, d), 7.99(1H, d), 7.90-7.83(3H, m), 7.77-7.68(6H, m), 7.61-7.51(8H, m), 7.29(1H, d) 189 δ = 8.76-8.71(3H, m), 8.63(1H, d), 8.52-8.48(2H, m), 8.39-8.33(3H, m), 8.20(1H, d), 7.99(1H, d), 7.90-7.83(3H, m), 7.77-7.68(6H, m), 7.61-7.51(10H, m), 7.29-7.27(2H, m) 197 δ = 9.12 (2H, s), 8.80-8.63 (6H, m), 8.52-8.39 (4H, m), 8.28-8.20 (3H, m), 7.99-7.90 (2H, m), 7.87-7.83 (2H, m), 7.74 (1H, t), 7.68-7.54 (5H, m), 7.29 (1H, d) 200 δ = 8.82 (1H, d), 8.71-8.69 (2H, m), 8.52-8.47 (3H, m), 8.33-8.31 (2H, m), 8.25-8.20 (2H, m), 7.99 (1H, d), 7.90-7.83 (3H, m), 7.77-7.68 (6H, m), 7.61-7.49 (10H, m), 7.29-7.27 (2H, m) 219 δ = 9.12 (2H, s), 8.80-8.71 (4H, m), 8.63 (1H, d), 8.52-8.45 (3H, m), 8.28-8.20 (3H, m), 8.10-7.99 (3H, m), 7.90-7.83 (3H, m), 7.74-7.68 (2H, m), 7.61-7.54 (4H, m), 7.29 (1H, d) 227 δ = 9.63 (1H, s), 9.04 (1H, d), 8.81 (1H, d), 8.71-8.65 (3H, m), 8.36-8.30 (3H, m), 8.20 (1H, d), 7.99-7.83 (6H, m), 7.77-7.63 (6H, m), 7.61-7.51 (8H, m), 7.29 (1H, d) 233 δ = 8.76-8.71(3H, m), 8.63(1H, d), 8.39-8.33(5H, m), 8.20(1H, d), 7.99-7.90(4H, m), 7.83(1H, d), 7.77-7.68(5H, m), 7.61-7.49(10H, m), 7.29-7.27(2H, m) 238 δ = 9.63(1H, s), 8.81(1H, d), 8.71-8.63(5H, m), 8.39-8.36(3H, m), 8.20(1H, d), 7.99-7.90(4H, m), 7.83(1H, d), 7.77-7.61(7H, m), 7.57-7.51(7H, m), 7.29(1H, d) 248 δ = 9.18 (1H, d), 8.82 (1H, d), 8.71 (1H, d), 8.55 (1H, d), 8.47-8.36 (5H, m), 8.25-8.20 (2H, m), 7.99-7.83 (5H, m), 7.77-7.68 (6H, m), 7.61-7.51 (7H, m), 7.29-7.23 (2H, m) 255 δ = 8.71-8.69 (2H, m), 8.63 (1H, d), 8.36-8.32 (4H, m), 8.20 (1H, d), 8.10-7.90 (7H, m), 7.77-7.61 (6H, m), 7.55-7.49 (9H, m), 7.29-7.27 (2H, m) 257 δ = 8.80 (1H, d), 8.71-8.63 (4H, m), 8.45 (1H, d), 8.20 (1H, d), 8.10-7.96 (7H, m), 7.90-7.85 (3H, m), 7.77-7.68 (5H, m), 7.61-7.51 (8H, m), 7.83 (1H, d), 7.29 (1H, d) 265 Total D substituents 268 Total D substituents 270 δ = 8.82 (1H, d), 8.52-8.47 (3H, m), 8.25 (1H, d), 7.99 (1H, d), 7.87-7.83 (2H, m), 7.74 (1H, t), 7.68-7.61 (2H, m) 272 Total D substituents [table 5] Compound FD-MS Compound FD-MS 1 m/z= 633.20 (C43H28N3OP=633.69) 2 m/z= 709.23 (C49H32N3OP=709.79) 18 m/z= 710.22 (C48H31N4OP=710.78) twenty four m/z= 709.23 (C49H32N3OP=709.79) 35 m/z= 709.23 (C49H32N3OP=709.79) 50 m/z= 710.22 (C48H31N4OP= 710.78) 64 m/z= 635.19 (C41H26N5OP=635.67) 68 m/z= 709.23 (C49H32N3OP=709.79) 78 m/z= 633.20 (C43H28N3OP= 633.69) 92 m/z= 709.23 (C49H32N3OP= 709.79) 93 m/z= 709.23 (C49H32N3OP=709.79) 100 m/z= 633.20 (C43H28N3OP=633.69) 101 m/z= 709.23 (C49H32N3OP=709.79) 113 m/z= 759.24 (C53H34N3OP=759.85) 127 m/z= 710.22 (C48H31N4OP= 710.78) 133 m/z= 633.20 (C43H28N3OP=633.69) 135 m/z= 759.24 (C53H34N3OP= 759.85) 145 m/z= 709.23 (C49H32N3OP= 709.79) 160 m/z= 710.22 (C48H31N4OP= 710.78) 171 m/z= 710.22 (C48H31N4OP= 710.78) 186 m/z= 635.19 (C41H26N5OP= 635.67) 188 m/z= 633.20 (C43H28N3OP=633.69) 189 m/z= 709.23 (C49H32N3OP=709.79) 197 m/z= 635.19 (C41H26N5OP=635.67) 200 m/z= 709.23 (C49H32N3OP= 709.79) 219 m/z= 635.19 (C41H26N5OP= 635.67) 227 m/z= 710.22 (C48H31N4OP= 710.78) 233 m/z= 709.23 (C49H32N3OP= 709.79) 238 m/z= 710.22 (C48H31N4OP=710.78) 248 m/z= 710.22 (C48H31N4OP= 710.78) 255 m/z= 709.23 (C49H32N3OP= 709.79) 257 m/z= 709.23 (C49H32N3OP= 709.79) 265 m/z= 661.37 (C43D28N3OP= 661.86) 268 m/z= 661.37 (C43D28N3OP= 661.86) 270 m/z= 730.36 (C49H11D21N3OP= 730.92) 272 m/z= 741.43 (C49D32N3OP= 741.98) [ Experimental Example ] < Experimental Example 1> 1 ) Production of organic light-emitting device

The transparent electrode indium tin oxide (ITO) film obtained from OLED glass (manufactured by Samsung-Corning Co., Ltd.) was ultrasonically washed for 5 minutes using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then the ITO film was placed in isopropyl alcohol, stored, and then used. Next, the ITO substrate was placed in a substrate folder of a vacuum deposition apparatus, and the following 4,4',4''-tri(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum deposition apparatus.

Subsequently, the air in the chamber was evacuated until the vacuum degree in the chamber reached 10 ^-6 Torr, and then a hole injection layer with a thickness of 600 angstroms was deposited on the ITO substrate by applying a current to the cell to evaporate 2-TNATA. A hole transport layer with a thickness of 300 angstroms was deposited on the hole injection layer by placing the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) in another cell of the vacuum deposition apparatus and applying a current to the cell to evaporate NPB.

A hole injection layer and a hole transport layer are formed as described above, and then a blue light-emitting material having the following structure is deposited on the hole injection layer and the hole transport layer as a light-emitting layer. Specifically, a blue light-emitting host material H1 is vacuum deposited to a thickness of 200 angstroms on a cell in a vacuum deposition device, and a blue light-emitting dopant material D1 is vacuum deposited on the blue light-emitting host material H1 in an amount of 5% based on the host material.

Subsequently, a compound having the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transport layer.

The OLED device was fabricated by depositing lithium fluoride (LiF) with a thickness of 10 angstroms as an electron injection layer and enabling the Al negative electrode to have a thickness of 1,000 angstroms. At the same time, all organic compounds required for fabricating OLED devices were subjected to vacuum sublimation purification at 10 ^-8 torr to 10 ^-6 torr for each material and used to fabricate OLEDs.

Organic electroluminescent elements (Examples 1 to 36 and Comparative Examples 2 to 4) were manufactured in the same manner as in Comparative Example 1, except that the compounds shown in Table 6 below were used instead of E1 used in forming the electron transport layer in Comparative Example 1. 2 ) Driving voltage and luminous efficiency of organic electroluminescent element

For the organic electroluminescent elements of Examples 1 to 36 and Comparative Examples 1 to 4 manufactured as above, electroluminescent light emission (EL) characteristics were measured using M7000 manufactured by McScience Inc., and using the measurement results, T 95 when the standard brightness was 3,500 candela/square meter (cd/m ² ) was measured using a service life measurement device (M6000) manufactured by McScience Inc. The results of measuring the driving voltage, luminous efficiency, color coordinates (International Illumination Commission (Commission Internationale de l´Eclairage, CIE)) and service life (T ₉₅ , unit: h) of the blue organic electroluminescent element manufactured according to _the present invention are shown in the following Table 6. [Table 6] Compound Driving voltage (V) Luminous efficiency (candela/area) CIE (x, y) Service life (T ₉₅ ) Example 1 1 5.13 6.83 (0.134, 0.100) 83 Example 2 2 5.20 6.83 (0.133, 0.100) 88 Example 3 18 5.21 6.80 (0.133, 0.102) 89 Example 4 twenty four 5.18 6.80 (0.133, 0.100) 85 Example 5 35 5.20 6.79 (0.133, 0.101) 88 Example 6 50 5.21 6.79 (0.133, 0.101) 87 Example 7 64 5.15 6.78 (0.134, 0.101) 84 Example 8 68 5.28 6.90 (0.133, 0.101) 86 Example 9 78 5.30 6.85 (0.133, 0.102) 86 Example 10 92 5.24 6.93 (0.132, 0.100) 88 Example 11 93 5.20 6.95 (0.133, 0.101) 89 Example 12 100 5.22 6.81 (0.134, 0.100) 90 Example 13 101 5.34 6.88 (0.133, 0.100) 88 Example 14 113 5.32 6.80 (0.134, 0.101) 87 Example 15 127 5.32 6.81 (0.133, 0.100) 85 Example 16 133 5.28 6.82 (0.132, 0.100) 83 Example 17 135 5.18 6.85 (0.133, 0.101) 88 Example 18 145 5.25 6.88 (0.133, 0.100) 84 Example 19 160 5.23 6.82 (0.134, 0.101) 84 Example 20 171 5.25 6.82 (0.132, 0.100) 85 Example 21 186 5.22 6.89 (0.133, 0.103) 87 Example 22 188 5.29 6.84 (0.133, 0.102) 85 Example 23 189 5.29 6.81 (0.134, 0.101) 84 Example 24 197 5.25 6.88 (0.134, 0.102) 88 Example 25 200 5.25 6.90 (0.133, 0.102) 83 Example 26 219 5.19 6.81 (0.133, 0.102) 87 Example 27 227 5.20 6.83 (0.133, 0.102) 85 Example 28 233 5.18 6.86 (0.133, 0.100) 87 Example 29 238 5.30 6.80 (0.133, 0.102) 88 Example 30 248 5.30 6.83 (0.133, 0.102) 85 Example 31 255 5.31 6.81 (0.133, 0.101) 88 Example 32 257 5.29 6.75 (0.134, 0.100) 83 Example 33 265 5.13 6.78 (0.134, 0.101) 91 Example 34 268 5.15 6.86 (0.133, 0.101) 90 Example 35 270 5.19 6.83 (0.133, 0.101) 99 Example 36 272 5.25 6.84 (0.134, 0.100) 98 Comparison Example 1 E1 5.88 6.15 (0.134, 0.100) 35 Comparison Example 2 Comparison with Compound A 5.75 6.23 (0.133, 0.102) 56 Comparison Example 3 Comparison with Compound B 5.78 6.28 (0.132, 0.100) 58 Comparison Example 4 Comparison with Compound C 5.68 6.327 (0.134, 0.101) 58

Comparative compounds A to C used in Table 6 are as follows.

As can be seen from the results shown in Table 6, it can be confirmed that compared with Comparative Examples 1 to Comparative Examples 4, the organic light-emitting elements in Examples 1 to 36 in which the heterocyclic compound of the present application is used as the material of the electron transport layer of the blue organic light-emitting element have low driving voltage and significantly improved luminous efficiency and service life.

These results are determined due to the following fact: when the heterocyclic compound according to the present application is used as a material for an organic material layer of an organic light-emitting element, particularly as an electron transport layer in the organic material layer, the phosphine oxide functional group and the phenanthroline functional group of the heterocyclic compound according to the present application can efficiently transfer electrons due to stable bonding with the metal used for the negative electrode.

That is, it is shown that when the heterocyclic compound according to the present application is used as a material for the electron transport layer of an organic light-emitting element, the electron transport characteristics and stability of the element are improved, and thus the element is excellent in all aspects of drive, efficiency and service life. < Experimental Example 2> Fabrication of an organic light-emitting element 1 ) Fabrication of an organic light-emitting element

The glass substrate on which ITO was thinly coated to a thickness of 1500 angstroms was ultrasonically cleaned with distilled water. When the washing with distilled water was completed, the glass substrate was ultrasonically cleaned with a solvent (such as acetone, methanol, and isopropyl alcohol), dried, and then subjected to ultraviolet ozone (UVO) treatment for 5 minutes using UV in an ultraviolet (UV) cleaning machine. Thereafter, the substrate was transferred to a plasma cleaning machine (PT), and then subjected to plasma treatment in a vacuum state to achieve an ITO work function and remove residual films, and thus the substrate was transferred to a thermal deposition device for organic deposition.

An organic material having a 2-stacked white organic light device (WOLED) structure is formed on an ITO transparent electrode (positive electrode). For the first stack, first, a hole transport layer having a thickness of 300 angstroms is formed by thermal vacuum deposition of cyclohexylidenebis [N,N-bis(4-methylphenyl)benzenamine] (TAPC). The hole transport layer is formed, and then, a light-emitting layer is thermally vacuum deposited on the hole transport layer as described below. A light-emitting layer having a thickness of 300 angstroms is deposited by doping the host TCz1 with a blue phosphorescent dopant FIrpic at a concentration of 8%. An electron transport layer was formed to a thickness of 400 angstroms by using TmPyPB, and then a charge generation layer was formed to a thickness of 100 angstroms by doping the compound described in the following Table 6 with Cs ₂ CO ₃ at a concentration of 20%.

For the second stack, first, a hole injection layer with a thickness of 50 angstroms was formed by thermal vacuum deposition of MoO _3. A hole transport layer with a thickness of 100 angstroms was formed as a common layer by doping TAPC with MoO ₃ at a concentration of 20%, and then a thickness of 300 angstroms was formed by depositing TAPC. A light-emitting layer with a thickness of 300 angstroms was deposited on the hole transport layer by doping the host TCz1 with a concentration of 8% of the green phosphorescent dopant Ir(ppy) ₃ , and then an electron transport layer with a thickness of 600 angstroms was formed using TmPyPB. Finally, an organic electroluminescent element (Examples 37 to 72 and Comparative Examples 5 to 8) was manufactured by depositing lithium fluoride (LiF) with a thickness of 10 angstroms on the electron transport layer to form an electron injection layer, and then depositing an aluminum (Al) negative electrode with a thickness of 1,200 angstroms on the electron injection layer to form a negative electrode.

At the same time, for each material, all organic compounds required for manufacturing OLED elements were subjected to vacuum sublimation purification at 10 ^-8 Torr to 10 ^-6 Torr and used to manufacture OLEDs. 2 ) Driving voltage and luminescence efficiency of organic electroluminescent elements

For the organic electroluminescent elements of Examples 37 to 72 and Comparative Examples 5 to 8 manufactured as above, electroluminescent light emission (EL) characteristics were measured by M7000 manufactured by Mike Scientific, and based on the measurement results, T ₉₅ was measured at a standard brightness of 3,500 candelas/square meter (cd/m ² ) using a life measurement device (M6000) manufactured by Mike Scientific.

The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE) and service life (T ₉₅ , unit: h) of the white organic electroluminescent element manufactured according to the present invention are shown in the following Table 7. [Table 7] Compound Driving voltage (V) Luminous efficiency (candela/area) CIE (x, y) Service life (T ₉₅ ) Example 37 1 7.13 65.45 (0.210, 0.430) 87 Example 38 2 7.15 68.76 (0.211, 0.428) 82 Example 39 18 7.23 68.90 (0.213, 0.425) 88 Example 40 twenty four 7.18 69.05 (0.212, 0.425) 87 Example 41 35 7.20 70.33 (0.212, 0.425) 85 Example 42 50 7.20 70.03 (0.213, 0.425) 85 Example 43 64 7.25 69.13 (0.208, 0.430) 84 Example 44 78 7.20 69.82 (0.213, 0.425) 85 Example 45 68 7.18 68.88 (0.208, 0.430) 88 Example 46 92 7.19 69.85 (0.213, 0.430) 85 Example 47 93 7.20 70.05 (0.214, 0.430) 89 Example 48 100 7.14 69.53 (0.210, 0.430) 90 Example 49 101 7.15 69.03 (0.211, 0,429) 89 Example 50 113 7.23 69.55 (0.212, 0.429) 85 Example 51 127 7.15 69.00 (0.213, 0.425) 88 Example 52 133 7.22 68.77 (0.212, 0.430) 85 Example 53 135 7.18 66.47 (0.215, 0.425) 82 Example 54 145 7.20 67.75 (0.212, 0.423) 83 Example 55 160 7.19 67.83 (0.213, 0.425) 83 Example 56 171 7.20 67.77 (0.212, 0.425) 82 Example 57 186 7.18 67.53 (0.218, 0.428) 85 Example 58 188 7.15 67.72 (0.209, 0.429) 87 Example 59 189 7.19 69.58 (0.213, 0.428) 88 Example 60 197 7.23 69.23 (0.212, 0.430) 88 Example 61 200 7.20 70.13 (0.213, 0.425) 84 Example 62 219 7.18 68.93 (0.212, 0.425) 83 Example 63 227 7.20 69.05 (0.212, 0.425) 83 Example 64 233 7.17 68.66 (0.214, 0.425) 84 Example 65 238 7.18 69.83 (0.214, 0.428) 84 Example 66 248 7.18 69.90 (0.213, 0.425) 83 Example 67 255 7.20 68.84 (0.218, 0.427) 85 Example 68 257 7.22 67.32 (0.210, 0.425) 90 Example 69 265 7.20 70.32 (0.213, 0.429) 98 Example 70 268 7.24 70.13 (0.210, 0.429) 101 Example 71 270 7.19 69.87 (0.214, 0.430) 96 Example 72 272 7.18 69.67 (0.213, 0.425) 98 Comparison Example 5 PcqI 8.20 47.71 (0.210, 0.430) 46 Comparative Example 6 Comparison with Compound A 7.85 54.22 (0.213, 0.430) 57 Comparison Example 7 Comparison with Compound B 7.84 58.47 (0.209, 0.428) 53 Comparative Example 8 Comparison with Compound C 7.88 58.62 (0.210, 0.428) 56

Comparative compounds A to C used in Table 7 are the same as the compounds used in Experimental Example 1.

As can be seen from the results shown in Table 7, it can be confirmed that compared with Comparative Examples 5 to 8, the organic electroluminescent elements of Examples 37 to 72 in which the heterocyclic compound according to the present application is used as the charge generating layer material of the 2-stacked white organic electroluminescent element have low driving voltage and improved service life and luminous efficiency.

The reason for determining these results is due to the fact that when the heterocyclic compound according to the present application is used as a material for an organic material layer (for a charge generating layer among the organic material layers) of an organic light-emitting element, the phosphine oxide functional group and the phenanthroline functional group of the heterocyclic compound according to the present application can form a stable bond with a metal used as an electrode.

More specifically, when the heterocyclic compound according to the present application is used as an N-type charge generation layer, a stable gap state is formed in the N-type charge generation layer. This may be because electrons generated from the P-type charge generation layer are injected into the electron transport layer through the gap state generated in the N-type charge generation layer.

When a gap state is stably formed in the charge generation layer in this manner, electron transfer from the P-type charge generation layer to the N-type charge generation layer occurs efficiently.

That is, when the heterocyclic compound according to the present application is used as an N-type charge generation layer, it has the following effects: reducing the driving voltage of the organic light-emitting element and improving the efficiency and service life.

100: substrate 200: positive electrode 300: organic material layer 301: hole injection layer 302: hole transport layer 303: luminescent layer 304: hole blocking layer 305: electron transport layer 306: electron injection layer 400: negative electrode

1 to 4 are diagrams each schematically showing a stacked structure of an organic light emitting element according to an exemplary embodiment of the present application.

100: Substrate

200: Positive electrode

300: Organic material layer

400: Negative electrode

Claims (15)

A heterocyclic compound represented by the following chemical formula 1: [Chemical formula 1] Wherein, in Chemical Formula 1, L1 and L2 are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, m1 and m2 are integers from 0 to 3, and when m1 is 2 or greater than 2, L1 in the brackets are the same or different from each other, and when m2 is 2 or greater than 2, L2 in the brackets are the same or different from each other, R1 to R3 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, a is an integer from 0 to 3, b and c are each an integer from 0 to 4, and when a is 2 or more, R1 in the brackets are the same or different from each other, and when b is 2 or more, R2 in the brackets are the same or different from each other, and when c is 2 or more, R3 in the brackets are the same or different from each other, and A1 and A2 are the same or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a group represented by the following chemical formula A, [Chemical formula A] In Formula A, Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, is bonded to the position of L1 or L2 of Chemical Formula 1, and at least one of A1 and A2 is a group represented by Chemical Formula A. The heterocyclic compound as described in claim 1, wherein A1 and A2 are the same or different from each other and are each independently a group represented by the following chemical formula B or a group represented by chemical formula A, [chemical formula B] In Formula B, R4 and R5 are the same or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 in the parentheses are the same or different from each other, and when e is 2 or greater, R5 in the parentheses are the same or different from each other, and It is the position bonded to L1 or L2 of Chemical Formula 1. The heterocyclic compound as described in claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1 or Chemical Formula 1-2: [Chemical Formula 1-1] [Chemical formula 1-2] In Chemical Formulae 1-1 and 1-2, L1, L2, Ar1, Ar2, R1 to R3, m1, m2, and a to e are defined the same as in Chemical Formula 1, R4 and R5 are the same as or different from each other, and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and d is an integer from 0 to 2, e is an integer from 0 to 5, and when d is 2, R4 in the parentheses are the same as or different from each other, and when e is 2 or greater, R5 in the parentheses are the same as or different from each other. The heterocyclic compound as described in claim 3, wherein Chemical Formula 1-1 is represented by any one of the following Chemical Formulas 1-1-1 to 1-1-3: [Chemical Formula 1-1-1] [Chemical formula 1-1-2] [Chemical formula 1-1-3] In Chemical Formula 1-1-1 to Chemical Formula 1-1-3, the definitions of L1, L2, Ar1, Ar2, R1 to R5, m1, m2, and a to e are the same as those in Chemical Formula 1-1. The heterocyclic compound as described in claim 3, wherein Chemical Formula 1-2 is represented by any one of the following Chemical Formulas 1-2-1 to 1-2-3: [Chemical Formula 1-2-1] [Chemical formula 1-2-2] [Chemical formula 1-2-3] In Chemical Formula 1-2-1 to Chemical Formula 1-2-3, the definitions of L1, L2, Ar1, Ar2, R1 to R5, m1, m2, and a to e are the same as those in Chemical Formula 1-2. The heterocyclic compound as described in claim 1, wherein the deuterium content of the heterocyclic compound represented by Chemical Formula 1 is 0% to 100%. The heterocyclic compound as described in claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds: An organic light-emitting element comprises: a first electrode; a second electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain the heterocyclic compound as described in any one of claims 1 to 7. The organic light-emitting device as described in claim 8, wherein the organic material layer includes an electron transport layer, and the electron transport layer contains the heterocyclic compound. The organic light-emitting device as described in claim 8 further includes one layer or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer. An organic light-emitting element as described in claim 8, wherein the organic light-emitting element includes: a first electrode; a first stack, disposed on the first electrode and including a first light-emitting layer; a charge generating layer, disposed on the first stack; a second stack, disposed on the charge generating layer and including a second light-emitting layer; and a second electrode, disposed on the second stack. The organic light-emitting device as described in claim 11, wherein the charge generating layer comprises the heterocyclic compound. The organic light-emitting device as described in claim 12, wherein the charge generation layer is an N-type charge generation layer. A composition for an organic material layer of an organic light-emitting device, comprising the heterocyclic compound as described in any one of claims 1 to 7. A method for manufacturing an organic light-emitting element, the method comprising: Preparing a substrate; Forming a first electrode on the substrate; Forming an organic material layer having one or more layers on the first electrode; and Forming a second electrode on the organic material layer, Wherein the forming of the organic material layer comprises forming the organic material layer having one or more layers by using the composition described in claim 14.