KR20240055430A - Compound and organic light-emitting device comprising same - Google Patents

Abstract

This specification provides a compound and an organic light-emitting device containing the same.

Description

Compound and organic light-emitting device containing the same {COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME}

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

An electroluminescent device is a type of self-luminous display device and has the advantage of a wide viewing angle, excellent contrast, and fast response speed.

Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light emitting device with this structure, electrons and holes injected from two electrodes combine in the organic thin film to form a pair and then annihilate, emitting light. The organic thin film may be composed of a single layer or multiple layers, depending on need.

The material for the organic thin film may be a compound that can perform the functions of hole transport, hole transport assistance, and electron blocking.

In order to improve the performance, efficiency, and lifespan of organic light-emitting devices, the development of organic thin film materials is continuously required.

US Patent No. 4,356,429

The present invention seeks to provide a compound and an organic light-emitting device containing the same.

In an exemplary embodiment of the present application, a compound represented by the following formula (1) is provided.

[Formula 1]

In Formula 1,

L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,

One of Z1 and Z2 is -NAr1Ar2, and the other is a substituted or unsubstituted aryl group of C6 to C60; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof,

R1 to R3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; Substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; and -P(=O)RR'; or adjacent groups of R1 to R3 combine to form a ring,

R, R' and R" are the same or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A substituted or unsubstituted C2 to C60 heteroaryl group;

m1 and p1 are the same or different from each other and are each independently an integer from 0 to 4,

n1 and q1 are the same or different from each other and are each independently an integer of 1 to 4,

a is an integer from 0 to 4,

b is an integer from 0 to 3,

When each of a, b, m1, n1, p1 and q1 is 2 or more, each of R1, R2, L1, L2, Z1 and Z2 is the same or different from each other.

Additionally, in an exemplary embodiment of the present application, a first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. do.

The compounds described in this specification can be used as organic layer materials for organic light-emitting devices. In other words, it can serve as a light emitting material, hole injection material, hole transport material, hole transport auxiliary material, electron blocking material, electron transport material, electron injection material, etc. in an organic light emitting device. In particular, it can be used as a material for a hole transport layer, a hole transport auxiliary layer, and/or an electron blocking layer of an organic light emitting device.

Specifically, one or two or more types of compounds represented by Formula 1 may be used, and may be used as materials for a hole transport layer, a hole transport auxiliary layer, and an electron blocking layer. In particular, it can be used as a material for the hole transport layer, hole transport auxiliary layer, and electron blocking layer of organic light-emitting devices by introducing various substituents and changing the bonding positions of the substituents to adjust the bandgap.

The compound of the present invention is characterized by a disubstituted structure in which at least two substituents are connected to an indenofluorene core skeleton, and specific examples of substituents include (1) an amine-based substituent and (2) an aryl group or heteroaryl group introduced. It can be. In addition, the above-mentioned substituents (1) and (2) are bonded to a specific position and number of substitutions on the indenofluorene core skeleton, thereby increasing electron mobility due to the appropriate bond length and strength of the bonded substituents such as amine group and aryl group. Implemented at a speed suitable for the device, it forms a more stable compound, providing the advantage of efficiently transferring electrons without decomposition or destruction of the compound.

In particular, when the compound of the present invention is used in the hole transport layer, hole transport auxiliary layer, and electron blocking layer of an organic light emitting device, the driving voltage of the device is lowered, the efficiency of the device is increased, or the lifespan is increased. You can.

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

Hereinafter, this specification will be described in more detail.

In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components unless specifically stated to the contrary.

In this specification, the chemical formula means the position where it is combined.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.

In this specification, “substituted or unsubstituted” means deuterium; halogen group; -CN; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; Aryloxy group of C6 to C60; C1 to C60 alkylthioxy group; Arylthioxy group of C6 to C60; C1 to C60 alkyl sulfoxy group; C6 to C60 aryl sulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; Aryl group of C6 to C60; C2 to C60 heteroaryl group; means that one or more substituents selected from the group consisting of -SiRR'R"; -P(=O)RR'; and -NRR', or two or more substituents selected from the above exemplified substituents are substituted or unsubstituted with a connected substituent; , R, R' and R" are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; and a substituent consisting of at least one of a heteroaryl group.

In this specification, “if a substituent is not indicated in the chemical formula or compound structure” means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( ^2H , Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In an exemplary embodiment of the present application, “when a substituent is not indicated in the chemical formula or compound structure” may mean that all positions that can appear as substituents are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the content of deuterium may be 0% to 100%.

In an exemplary embodiment of the present application, in “cases where substituents are not indicated in the chemical formula or compound structure,” the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen, etc., explicitly excluding deuterium. Otherwise, hydrogen and deuterium can be used together in compounds.

In an exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element that has a deuteron, consisting of one proton and one neutron, as its nucleus. Hydrogen- It can be expressed as 2, and the element symbol can also be written as D or ² H.

In an exemplary embodiment of the present application, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A). Isotopes have the same number of protons but do not contain neutrons. It can also be interpreted as an element with a different number of neutrons.

In an exemplary embodiment of the present application, the meaning of the content T% of a specific substituent means that the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2. It can be defined as /T1Х100 = T%.

That is, in one example, The deuterium content of 20% in the phenyl group represented by means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuteriums among them is 1 (T2 in the formula), it will be expressed as 20%. You can. That is, the deuterium content of 20% in the phenyl group can be expressed by the following structural formula.

Additionally, in an exemplary embodiment of the present application, “a phenyl group with a deuterium content of 0%” may mean a phenyl group that does not contain deuterium atoms, that is, has 5 hydrogen atoms.

In this specification, 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 further substituted by another substituent. The carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group Tyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methyl Examples include pentyl group, 4-methylhexyl group, and 5-methylhexyl group, but it is not limited thereto.

In the present specification, the alkenyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited to these.

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

In this specification, a haloalkyl group refers to an alkyl group substituted with a halogen group, and specific examples include -CF ₃ and -CF ₂ CF ₃ , but are not limited thereto.

In this specification, the alkoxy group is represented by -O(R101), and examples of the above-described alkyl group may be applied to R101.

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

In this specification, the alkylthioxy group is represented by -S(R103), and examples of the alkyl groups described above may be applied to R103.

In the present specification, the arylthioxy group is represented by -S(R104), and examples of the above-described aryl groups may be applied to R104.

In the present specification, the alkyl sulfoxy group is represented by -S(=0) ₂ (R105), and examples of the above-described alkyl groups may be applied to R105.

In the present specification, the arylsulfoxy group is represented by -S(=0) ₂ (R106), and examples of the above-described aryl groups may be applied to R106.

In the present specification, a cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms and may be further substituted by another substituent. Here, polycyclic refers to a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2 , 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.

In the present specification, the heterocycloalkyl group contains O, S, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic refers to a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the aryl group include phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, and phenalenyl group. , pyrenyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, these Condensation ring groups, etc. may be included, but are not limited thereto.

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

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

When the fluorenyl group is substituted, it may include the following structural formula, but is not limited thereto.

In the present specification, the heteroaryl group contains S, O, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, heterocycloalkyl group, or aryl group. The carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridine group, pyrrole group, pyrimidine group, pyridazine group, furan group, thiophene group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, furazine group, oxadiazole group, thiadiazole group, dithiazole group, tetrazolyl group, pyran group, thiopyran group, diazine group, oxazine group, thiazine group, dioxine group, triazine group, tetrazine group, quinoline group, Isoquinoline group, quinazoline group, isoquinazoline group, quinozoline group, naphthyridine group, acridine group, phenanthridine group, imidazopyridine group, diazanaphthalene group, triazindene group, indole group, indolizine group, Benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzo Sylol group, spirobi (dibenzosilol), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo [2,3-a] carbazole group, indolo [2,3-b] carbazole group, Indoline group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazole group, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5, 10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1, Examples include, but are not limited to, 2-a]imidazo[1,2-e]indoline group and 5,11-dihydroindeno[1,2-b]carbazole group.

In this specification, when the substituent is a carbazole group, it means bonding with the nitrogen or carbon of carbazole.

In this specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

In this specification, an example of a benzocarbazole group may have any one of the following structures.

In the present specification, an example of a dibenzocarbazole group may have any one of the following structures.

In this specification, an example of a naphthobenzofuran group may have any one of the following structures.

In this specification, an example of a naphthobenzothiophene group may have any one of the following structures.

In the present specification, the silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specific examples of silyl groups include: (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), etc., but is 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 are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. Specifically, it may be substituted with an alkyl group or an aryl group, and the examples described above may be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, dimethylphosphine oxide, diphenylphosphine oxide, and dinaphthylphosphine oxide.

In this specification, the amine group is represented by -N(R112)(R113), and R112 and R113 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Alkyl group; alkenyl group; Alkoxy group; Cycloalkyl group; heterocycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heteroaryl group. The amine group is -NH ₂ ; Monoalkylamine group; monoarylamine group; Monoheteroarylamine group; dialkylamine group; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenyl fluores Examples include a nylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group, but are not limited to these.

In the present specification, the examples of the aryl group described above may be applied, except that the arylene group is a divalent group.

In the present specification, the examples of the heteroaryl group described above may be applied, except that the heteroarylene group is a divalent group.

As used herein, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.

Hydrocarbon rings and heterocycles that can be formed by adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and the rings are, respectively, the above-mentioned cycloalkyl group and aryl group, except that they are not monovalent. Structures exemplified by groups, heterocycloalkyl groups, and heteroaryl groups can be applied.

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

In an exemplary embodiment of the present application, a group not indicated as a substituent; Alternatively, it may mean that all groups represented by hydrogen can be replaced by deuterium. i.e. hydrogen; Alternatively, it may indicate that deuterium can be substituted for each other.

In general, compounds bonded with hydrogen and compounds substituted with deuterium show differences in thermodynamic behavior. This is because the mass of a deuterium atom is twice that of hydrogen, and due to the difference in the masses of the atoms, deuterium has the characteristic of having a lower vibration energy.

Additionally, the single bond dissociation energy of carbon and deuterium is higher than that of carbon and hydrogen. Therefore, the structure substituted with deuterium increases the thermal stability of the molecule, which has the effect of improving the lifespan of the device using it.

When a compound is deposited on a silicon wafer, materials containing deuterium tend to be packed with narrower intermolecular distances. In addition, when looking at the surface of the thin film using an atomic force microscope (AFM), it can be seen that the thin film made from a compound containing deuterium is deposited on a more uniform surface without any aggregates.

The compound of Formula 1 of the present application has a deuterium substitution rate of more than 0% and less than 100%. When deuterium is substituted, the ground state energy is lower than that of a hydrogen-substituted compound, and as the bond length between carbon and deuterium becomes shorter, the molecular core volume decreases. This can reduce electrical polarizability and make intermolecular interactions weaker, resulting in a more stable stacking structure when manufacturing devices.

These characteristics create an amorphous state in the thin film, leading to the effect of lowering the degree of crystallinity. In other words, the compound of Formula 1 can be effective in improving the heat resistance of OLED devices, which can improve lifespan and driving characteristics.

In an exemplary embodiment of the present application, a compound represented by the following formula (1) is provided.

[Formula 1]

In Formula 1,

L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,

One of Z1 and Z2 is -NAr1Ar2, and the other is a substituted or unsubstituted aryl group of C6 to C60; Or a substituted or unsubstituted C2 to C60 heteroaryl group,

Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof,

R1 to R3 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; Substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; and -P(=O)RR'; or adjacent groups of R1 to R3 combine to form a ring,

R, R' and R" are the same or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A substituted or unsubstituted C2 to C60 heteroaryl group;

m1 and p1 are the same or different from each other and are each independently an integer from 0 to 4,

n1 and q1 are the same or different from each other and are each independently an integer of 1 to 4,

a is an integer from 0 to 4,

b is an integer from 0 to 3,

When each of a, b, m1, n1, p1 and q1 is 2 or more, each of R1, R2, L1, L2, Z1 and Z2 is the same or different from each other.

In another embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Or it may be a substituted or unsubstituted C6 to C30 arylene group.

In another embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C20 arylene group.

In another exemplary embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C10 arylene group.

In another embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Alternatively, it may be a C6 to C10 arylene group substituted or unsubstituted with deuterium.

In another exemplary embodiment, L1 and L2 are the same or different from each other and are each independently directly bonded; Alternatively, it may be a phenylene group substituted or unsubstituted with deuterium.

In another embodiment, one of Z1 and Z2 is -NAr1Ar2, and the other is a substituted or unsubstituted aryl group of C6 to C40; Or it may be a substituted or unsubstituted C2 to C40 heteroaryl group.

In another embodiment, one of Z1 and Z2 is -NAr1Ar2, and the other is a substituted or unsubstituted aryl group of C6 to C30; Or it may be a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment, one of Z1 and Z2 is -NAr1Ar2, and the other is an aryl group of C6 to C30 unsubstituted or substituted with deuterium; Alternatively, it may be a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium.

In another embodiment, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group; Substituted or unsubstituted C2 to C40 heteroaryl group; Or it may be a combination thereof.

In another embodiment, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; Substituted or unsubstituted C2 to C30 heteroaryl group; Or it may be a combination thereof.

In another embodiment, Ar1 and Ar2 are the same or different from each other, and are each independently a C6 to C30 aryl group substituted or unsubstituted with deuterium; C2 to C30 heteroaryl group substituted or unsubstituted with deuterium; Or it may be a combination thereof.

In another exemplary embodiment, Ar1 and Ar2 are a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dimethyl fluorenyl group; Substituted or unsubstituted diphenyl fluorenyl group; A substituted or unsubstituted spirobifluorenyl group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Or it may be a combination thereof.

In another embodiment, Ar1 and Ar2 are phenyl groups unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Dimethyl fluorenyl group substituted or unsubstituted with deuterium; Diphetyl fluorenyl group substituted or unsubstituted with deuterium; Spirobifluorenyl group substituted or unsubstituted with deuterium; A furan group substituted or unsubstituted with deuterium; Thiophene substituted or unsubstituted with deuterium; A benzofuran group substituted or unsubstituted with deuterium; A benzothiophene group substituted or unsubstituted with deuterium; Dibenzofuran group substituted or unsubstituted with deuterium; Dibenzothiophene group substituted or unsubstituted with deuterium; Carbazole group substituted or unsubstituted with deuterium; Or it may be a combination thereof.

In another embodiment, one of Z1 and Z2, excluding -NAr1Ar2, is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dimethyl fluorenyl group; Substituted or unsubstituted diphenylfluorenyl group; A substituted or unsubstituted spirobifluorenyl group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Or it may be a combination thereof.

In another embodiment, one of Z1 and Z2, excluding -NAr1Ar2, is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Dimethyl fluorenyl group substituted or unsubstituted with deuterium; Diphetylfluorenyl group substituted or unsubstituted with deuterium; Spirobifluorenyl group substituted or unsubstituted with deuterium; A furan group substituted or unsubstituted with deuterium; Thiophene substituted or unsubstituted with deuterium; A benzofuran group substituted or unsubstituted with deuterium; A benzothiophene group substituted or unsubstituted with deuterium; Dibenzofuran group substituted or unsubstituted with deuterium; Dibenzothiophene group substituted or unsubstituted with deuterium; Carbazole group substituted or unsubstituted with deuterium; Or it may be a combination thereof.

In another exemplary embodiment, R1 to R3 are the same as or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C30 alkyl group; Substituted or unsubstituted C2 to C30 alkenyl group; Substituted or unsubstituted C2 to C30 alkynyl group; Substituted or unsubstituted C1 to C30 alkoxy group; Substituted or unsubstituted C3 to C30 cycloalkyl group; Substituted or unsubstituted C2 to C30 heterocycloalkyl group; Substituted or unsubstituted C6 to C30 aryl group; Substituted or unsubstituted C2 to C30 heteroaryl group; -SiRR'R"; and -P(=O)RR', or adjacent groups of R1 to R3 may be combined to form a C3 to C30 hydrocarbon ring or a C2 to C30 heterocycle. .

In another exemplary embodiment, R1 to R3 are the same as or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C2 to C20 alkenyl group; Substituted or unsubstituted C2 to C20 alkynyl group; A substituted or unsubstituted C1 to C20 alkoxy group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; Substituted or unsubstituted C2 to C20 heteroaryl group; -SiRR'R"; and -P(=O)RR', or adjacent groups of R1 to R3 may be combined to form a C3 to C20 hydrocarbon ring or a C3 to C20 heterocycle. .

In another exemplary embodiment, R1 to R3 are the same as or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C1 to C20 alkyl group; Substituted or unsubstituted C3 to C20 cycloalkyl group; Substituted or unsubstituted C2 to C20 heterocycloalkyl group; Substituted or unsubstituted C6 to C20 aryl group; and a substituted or unsubstituted C2 to C20 heteroaryl group.

In another exemplary embodiment, R1 to R3 are the same as or different from each other and are each independently hydrogen; Or it may be deuterium.

In another embodiment, R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C30 alkyl group; substituted or unsubstituted C3 to It may be a C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

In another embodiment, R, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C3 to It may be a C20 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C20 heteroaryl group.

In an exemplary embodiment of the present application, a is an integer from 0 to 4, and when a is 2 or more, R1 are the same or different from each other.

In another exemplary embodiment, a may be 0.

In another exemplary embodiment, a may be 1.

In another exemplary embodiment, a may be 2.

In another exemplary embodiment, a may be 3.

In another exemplary embodiment, a may be 4.

In an exemplary embodiment of the present application, b is an integer from 0 to 3, and when b is 2 or more, R2 are the same or different from each other.

In another exemplary embodiment, b may be 0.

In another exemplary embodiment, b may be 1.

In another exemplary embodiment, b may be 2.

In another exemplary embodiment, b may be 3.

In an exemplary embodiment of the present application, m1 and p1 are the same or different from each other and are integers from 0 to 4, and when m1 is 2 or more, L1 is the same or different from each other, and when p1 is 2 or more, L2 is the same or different from each other. do.

In another exemplary embodiment, m1 may be 0.

In another exemplary embodiment, m1 may be 1.

In another exemplary embodiment, m1 may be 2.

In another exemplary embodiment, m1 may be 3.

In another exemplary embodiment, m1 may be 4.

In another exemplary embodiment, p1 may be 0.

In another exemplary embodiment, p1 may be 1.

In another exemplary embodiment, p1 may be 2.

In another exemplary embodiment, p1 may be 3.

In another exemplary embodiment, p1 may be 4.

In an exemplary embodiment of the present application, n1 and q1 are the same or different from each other and are integers of 1 to 4, and when n1 is 2 or more, Z1 is the same or different from each other, and when q1 is 2 or more, Z2 is the same or different from each other. do.

In another exemplary embodiment, n1 may be 1.

In another exemplary embodiment, n1 may be 2.

In another exemplary embodiment, n1 may be 3.

In another exemplary embodiment, n1 may be 4.

In another exemplary embodiment, q1 may be 1.

In another exemplary embodiment, q1 may be 2.

In another exemplary embodiment, q1 may be 3.

In another exemplary embodiment, q1 may be 4.

In an exemplary embodiment of the present application, Formula 1 may be represented by any one of the following Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, L1, L2, Z1, Z2, R1 to R3, a, b, m1, n1, p1, and q1 are the same as defined in Formula 1, and details are described above. It is the same as what was said.

In an exemplary embodiment of the present application, the compound represented by Formula 1 may be represented by Formula 2 or 3 below.

[Formula 2]

[Formula 3]

In Formulas 2 and 3, each of R1 to R3, L1, Z1, L2, Z2, Ar1, Ar2, a, b, m1, n1, p1, and q1 is the same as the definition in Formula 1.

In an exemplary embodiment of the present application, the compound represented by Formula 2 may be represented by any one of the following Formulas 2-1 to 2-4.

[Formula 2-1]

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4, each of R1 to R3, L1, L2, Z2, Ar1, Ar2, a, b, m1, p1, and q1 is the same as the definition in Formula 1.

In an exemplary embodiment of the present application, Formula 3 may be represented by any one of the following Formulas 3-1 to 3-4.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Formulas 3-1 to 3-4, each of R1 to R3, L1, Z1, L2, Ar1, Ar2, a, b, m1, n1, and p1 is the same as the definition in Formula 1.

In an exemplary embodiment of the present application, -NAr1Ar2 of Formula 1 may be represented by any of the following structural formulas A, B, and C.

[Structural Formula A]

[Structural Formula B]

[Structural Formula C]

In the structural formulas A, B and C,

X1 is O, S, or NRa;

Ra is a substituted or unsubstituted C1 to C30 alkyl group; Or a substituted or unsubstituted aryl group of C6 to C30,

L33 and L44 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C30 arylene group; Or a substituted or unsubstituted C2 to C30 heteroarylene group,

Ar33 and Ar44 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C30,

R4 and R5 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C30 aryl group; is selected from the group consisting of a substituted or unsubstituted C2 to C30 heteroaryl group, or the adjacent groups of R4 and R5 combine to form a ring,

d is an integer from 0 to 8,

e is an integer from 0 to 7,

When each d and e is 2 or more, each R4 and R5 are the same or different from each other.

In another embodiment, X1 may be O.

In another embodiment, X1 may be S.

In another embodiment, X1 may be NRa.

In another embodiment, Ra is a substituted or unsubstituted C1 to C20 alkyl group; Or it may be a substituted or unsubstituted C6 to C20 aryl group.

In another embodiment, Ra is a substituted or unsubstituted C1 to C10 alkyl group; Or, it may be a substituted or unsubstituted C6 to C10 aryl group.

In another embodiment, Ra is a methyl group; ethyl group; profiler; butyl group; pentyl group; hexyl group; heptyl group; octyl group; phenyl group; or nathyl groups, which may further contain deuterium; Substituted or unsubstituted C1 to C10 alkyl group; Alternatively, it may be substituted or unsubstituted with a substituted or unsubstituted C6 to C10 aryl group.

In another embodiment, L33 and L44 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C30 arylene group; Or a substituted or unsubstituted C2 to C30 heteroarylene group,

In another embodiment, L33 and L44 are the same or different from each other and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C20 arylene group.

In another embodiment, L33 and L44 are the same or different from each other and are each independently directly bonded; Or, it may be a substituted or unsubstituted C6 to C10 arylene group.

In another embodiment, L33 and L44 are the same or different from each other and are each independently directly bonded; Alternatively, it may be a C6 to C10 arylene group substituted or unsubstituted with deuterium.

In another embodiment, L33 and L44 are the same or different from each other and are each independently directly bonded; Alternatively, it may be a phenylene group substituted or unsubstituted with deuterium.

In another embodiment, Ar33 and Ar44 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dimethyl fluorenyl group; Substituted or unsubstituted diphenylfluorenyl group; Or it may be a substituted or unsubstituted spirobifluorenyl group.

In another embodiment, Ar33 and Ar44 are the same or different from each other, and are each independently a phenyl group unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Dimethyl fluorenyl group substituted or unsubstituted with deuterium; Diphetylfluorenyl group substituted or unsubstituted with deuterium; Alternatively, it may be a spirobifluorenyl group substituted or unsubstituted with deuterium.

In another embodiment, R4 and R5 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C20 aryl group; It may be selected from the group consisting of a substituted or unsubstituted C2 to C20 heteroaryl group, or adjacent groups of R4 and R5 may be combined to form a substituted or unsubstituted C3 to C20 hydrocarbon ring or C2 to C20 heterocycle. there is.

In another embodiment, R4 and R5 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C10 aryl group; It may be selected from the group consisting of a substituted or unsubstituted C2 to C10 heteroaryl group, or adjacent groups of R4 and R5 may be combined to form a substituted or unsubstituted C3 to C10 hydrocarbon ring or C2 to C10 heterocycle. there is.

In another embodiment, R4 and R5 are the same or different from each other and are each independently hydrogen; Or it may be deuterium.

In another embodiment, d may be 0.

In another embodiment, d may be 1.

In another embodiment, d may be 2.

In another embodiment, d may be 3.

In another embodiment, d may be 4.

In another embodiment, d may be 5.

In another embodiment, d may be 6.

In another embodiment, d may be 7.

In another embodiment, d may be 8.

In another embodiment, e may be 0.

In another embodiment, e may be 1.

In another embodiment, e may be 2.

In another embodiment, e may be 3.

In another embodiment, e may be 4.

In another embodiment, e may be 5.

In another embodiment, e may be 6.

In another embodiment, e may be 7.

In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0%, or 1% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 5% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 10% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 15% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 20% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 25% to 100%.

In an exemplary embodiment of the present application, the deuterium content of the compound of Formula 1 may be 0%, or 30% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 50% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 70% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 0%, or 90% to 100%.

In another exemplary embodiment, the deuterium content of the compound of Formula 1 may be 0%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 30% to 100%.

In another embodiment, the deuterium content of the compound of Formula 1 may be 50% to 100%.

In another exemplary embodiment, the deuterium content of the compound of Formula 1 may be 70% to 100%.

In another exemplary embodiment, the deuterium content of the compound of Formula 1 may be 90% to 100%.

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

In an exemplary embodiment of the present application, the compound is an example, and is not limited thereto, and may include other compounds included in Formula 1 containing additional substituents. In addition, specific positions of deuterium substitution in the above compounds are excluded during the deuterium substitution and synthesis process, and hydrogen and deuterium may coexist.

Additionally, by introducing various substituents into the structure of Formula 1, a compound having the unique properties of the introduced substituent can be synthesized. For example, by introducing substituents mainly used in hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials used in the manufacture of organic light-emitting devices into the core structure, a material that satisfies the conditions required for each organic layer can be created. It can be synthesized.

In addition, the band gap can be finely adjusted by introducing various substituents into the structure of Formula 1 or changing the bonding position, and on the other hand, the characteristics at the interface between organic layers can be improved.

In addition, the compound of Formula 1 has excellent thermal stability, and this thermal stability provides driving stability to the organic light-emitting device and improves lifespan characteristics.

In an exemplary embodiment of the present application, a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. do.

In another exemplary embodiment, a first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes one type of compound represented by Formula 1. provides.

In another exemplary embodiment, a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes two or more types of compounds represented by Formula 1. Devices are provided.

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

In another exemplary embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

In an exemplary embodiment of the present application, the organic light emitting device may be a blue organic light emitting device.

In an exemplary embodiment of the present application, the organic light emitting device may be a green organic light emitting device.

In an exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device.

In an exemplary embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the compound represented by Formula 1 may be used as a material for the blue organic light-emitting device.

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

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

In this specification, specific details about the compound represented by Formula 1 are the same as those described above.

The organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include fewer organic material layers.

In one embodiment of the present invention, the organic material layer includes a hole transport layer (Host transfer layer: HTL), a hole transport auxiliary layer (Prime HTL), and an electron blocking layer (EBL), and the hole transport layer and the hole transport layer (EBL). At least one of the transport auxiliary layer and the electron blocking layer may include the compound represented by Formula 1 above.

In another organic light emitting device, the organic material layer includes a hole transport layer, a light emitting layer, or an electron blocking layer, and the hole transport layer, a light emitting layer, or an electron blocking layer may include the compound.

In another organic light emitting device, the organic material layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may include the compound.

In the present invention, Ir(ppy) ₃ , a green phosphorescent dopant, may be used as the iridium-based dopant.

In the present invention, (piq) ₂ (Ir)(acac), a red phosphorescent dopant, may be used as the iridium-based dopant.

In the present invention, the organic material layer of the organic light emitting device may include a light emitting layer.

In the present invention, the organic material layer of the organic light-emitting device includes a light-emitting layer, and the light-emitting layer may include a host material and/or a dopant material.

In another organic light-emitting device, the organic material layer may further include a light-emitting auxiliary layer or an N-type charge generation layer (N-CGL).

In the organic light emitting device of the present application, materials with a relatively high work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode 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); Combination of metal and oxide 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 are included, but are not limited to these.

As the cathode material, materials with a relatively low work function can be used, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

As the hole injection material, known hole injection materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994). Starburst type amine derivatives 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, a soluble conductive polymer, or poly( 3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate), Polyaniline/Camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) can be used.

As hole transport materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular or high molecular materials may also be used.

Electron transport materials include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, and fluorenone. Derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low molecular substances but also high molecular substances may be used.

For example, LiF is typically used as an electron injection material in the industry, but the present application is not limited thereto.

Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed. At this time, two or more light emitting materials can be deposited and used from individual sources, or they can be premixed and deposited from a single source. Additionally, a fluorescent material can be used as a light-emitting material, but it can also be used as a phosphorescent material. As a light-emitting material, a material that emits light by combining holes and electrons injected from an anode and a cathode, respectively, may be used, but materials that participate in light emission together with a host material and a dopant material may also be used.

When using a mixture of hosts of a light emitting material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more types of materials among an n-type host material or a p-type host material can be selected and used as a host material for the light emitting layer.

The organic light emitting device according to an exemplary embodiment of the present application may be a front emitting type, a rear emitting type, or a double-sided emitting type depending on the material used.

The compound according to an exemplary embodiment of the present application may function in organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors, on a principle similar to that applied to organic light-emitting devices.

The organic light-emitting device of the present invention may further include one 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 injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

The organic light emitting device of the present invention may further include one or two 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, a charge generation layer, an electron transport layer, and an electron injection layer. You can.

1 to 4 illustrate the stacking order of electrodes and organic material layers of an organic light-emitting device according to an exemplary embodiment of the present application. However, it is not intended that the scope of the present application be limited by these drawings, and structures of organic light-emitting devices known in the art may also be applied to the present application.

According to Figure 1, an organic light emitting device is shown in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, it is not limited to this structure, and an organic light-emitting device may be implemented in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG. 2.

Figures 3 and 4 illustrate the case where the organic material layer is multi-layered.

The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, an electron transport layer 304, and an electron injection layer 305. However, the scope of the present application is not limited by this laminated structure, and if necessary, the remaining layers except the light-emitting layer may be omitted, and other necessary functional layers may be added.

The organic material layer containing Formula 1 may additionally include other materials as needed.

In addition, the organic light emitting device according to an exemplary embodiment of the present application includes a first electrode, a second electrode, and two or more stacks provided between the first electrode and the second electrode, and the two or more stacks each independently include a light emitting layer. It includes a charge generation layer between the two or more stacks, and the charge generation layer includes the compound represented by Formula 1.

An organic light emitting device according to an exemplary embodiment of the present application includes a first electrode, a first stack provided on the first electrode and including a first stack light emitting layer, a charge generation layer provided on the first stack, and the charge It includes a second stack provided on the production layer and including a second stack light emitting layer, and a second electrode provided on the second stack. At this time, at least one of the first stack and the second stack may include the compound represented by Formula 1. In addition, the first stack and the second stack may each independently additionally include one or more of the above-described hole injection layer, hole transport layer, hole blocking layer, electron transport layer, and electron injection layer.

In an exemplary embodiment of the present application, the first stack may include a compound represented by Formula 1.

In an exemplary embodiment of the present application, the second stack may include a compound represented by Formula 1.

In an exemplary embodiment of the present application, the first hole transport layer of the first stack may include a compound represented by Formula 1.

In an exemplary embodiment of the present application, the second hole transport layer of the second stack may include a compound represented by Formula 1.

In this specification, the charge generation layer may be an N-type charge generation layer and may further include a dopant known in the art.

As an organic light emitting device according to an exemplary embodiment of the present application, an organic light emitting device with a 2-stack tandem structure is schematically shown in FIG. 4 below.

In one embodiment of the present application, preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; And forming a second electrode on the organic layer, wherein the forming the organic layer includes forming one or more organic layers using a composition for an organic layer according to an exemplary embodiment of the present application. A method for manufacturing an organic light emitting device is provided.

Below, the present specification is described in more detail through examples, but these are only for illustrating the present application and are not intended to limit the scope of the present application.

<Synthesis example>

[Preparation Example 1] Preparation of Compound 001

1) Preparation of compound 001-P4

2-bromo-1-iodo-9,9-dimethyl-9H-fluorene (20 g, 0.05012 mol, 1 eq), phenyl boronic acid (A) (6.55 g, 0.05262 mol, 1.05 eq), Pd(PPh ₃ ) ₄ (2.9g 0.00251 mol, 0.05 eq), K ₂ CO ₃ (17.32 g, 0.12529 mol, 2.5 eq), 1,4-dioxane (200 mL), and Water (60 mL) were added and stirred at 100°C for 6 h. . After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . By separation using a silica gel column, 18.1 g of compound 001-P4 was obtained with a yield of 98%.

2) Preparation of compound 001-P3

Compound 001-P4 (18.1 g, 0.0517 mol, 1 eq), (2-bromo-6-(methoxycarbonyl)phenyl)boronic acid (B) (14.08 g, 0.054 mol, 1.05 eq), Pd(PPh ₃ ) ₄ ( 2.98 g, 0.0026 mol, 0.05 eq), K2CO3 (17.8 g, 0.128 mol, 2.5 eq), 1,4-dioxane (180 mL), and Water (54 mL) were added and stirred at 100°C for 6 h. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . By separation using a silica gel column, 21.3 g of compound 001-P3 was obtained with a yield of 86.1%.

3) Preparation of Compound 001-P2

Compound 001-P3 (21.3 g, 0.045 mol, 1 eq) was added to ThF (210 mL) and stirred. Afterwards, MeMgBr (37.8 mL, 0.114 mol, 2.5 eq) was added and stirred at 70°C for 3 h. After completion of the reaction, the mixture was added dropwise to HCl (6 mL) and extracted using MC and water. Afterwards, moisture was removed with MgSO ₄ . By separation using a silica gel column, 20 g of compound 001-P2 was obtained with a yield of 86.5%.

4) Preparation of Compound 001-P1

Compound 001-P2 (20 g, 0.0438 mol, 1 eq) was added to DCM (200 mL) and stirred. Afterwards, BF ₃ O(C ₂ H ₅ ) ₂ (5.38 mL, 0.0436 mol, 1 eq) was added and stirred at room temperature for 1 h. After completion of the reaction, NaHCO3 aqueous solution (1M, 500 mL) was slowly added. Afterwards, the organic layer was extracted using MC and water, and moisture was removed with MgSO ₄ . Afterwards, it was separated using a silica gel column to obtain 18.8 g of compound 001-P1 with a yield of 86.8%.

5) Preparation of Compound 001

Compound 001-P1 (10 g, 0.0214, 1 eq), N-phenylaniline (C) (3.82 g, 0.0225 mol, 1.05 eq), Pd ₂ (dba) ₃ (0.98 g 0.001 mol, 0.05 eq), Xphos (1.02 g, 0.002 mol, 0.1 eq), NaOtBu (6.19 g, 0.0644 mol, 3 eq), and Toluene (100 mL) were added and stirred at 100°C for 6 h. After completion of the reaction, it was concentrated and separated using a silica gel column to obtain 11 g of Compound 001 with a yield of 93%.

In Preparation Example 1, intermediate A of Table 1 below was used instead of phenyl boronic acid (A), intermediate B was used instead of (2-bromo-6-(methoxycarbonyl)phenyl)boronic acid (B), and intermediate C was used instead of N-phenylaniline (C). The compound was synthesized using the same method.

compound
number intermediate
A intermediate
B intermediate
C transference number 001 93% 007 91% 024 83% 031 89% 043 91% 050 88% 067 93% 074 87% 082 81% 083 85% 084 87% 086 88% 098 72% 100 83% 104 81% 111 92%

[Preparation Example 2] Preparation of Compound 123

It was synthesized in the same manner as Preparation Example 1, except for the synthesis of compound 123 in Preparation Example 2.

1) Preparation of compound 123

Compound 123-P1 (10 g, 0.0214 mol, 1 eq), N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (C) (8.38 g, 0.0225 mol, 1.05 eq), Pd(PPh ₃ ) ₄ (1.24g 0.001 mol, 0.05 eq), K ₂ CO ₃ (7.42 g, 0.054 mol, 2.5 eq), 1,4-dioxane (100 mL ), Water (30 mL) was added and stirred at 100°C for 6 h. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . By separation using a silica gel column, 10.1 g of compound 123 was obtained with a yield of 74%.

In Preparation Example 2, intermediate A of Table 2 below was used instead of phenyl boronic acid (A), and intermediate B, N, N-diphenyl-4-(4) was used instead of (2-bromo-6-(methoxycarbonyl)phenyl)boronic acid (B). The compound was synthesized in the same manner using intermediate C instead of ,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (C).

compound number intermediate
A intermediate
B intermediate
C transference number 123 74% 135 88% 147 72% 154 76% 162 91% 171 89% 191 76% 200 77% 204 92% 214 90% 227 84% 239 88%

[Preparation Example 3] Preparation of compound 241

1) Preparation of compound 241-P4

2-bromo-1-iodo-9,9-dimethyl-9H-fluorene (20 g, 0.0501, 1 eq), N-phenylaniline (A) (8.9 g, 0.0526 mol, 1.05 eq), Pd ₂ (dba) ₃ (2.29g 0.0025 mol, 0.05 eq), After completion of the reaction, it was concentrated and separated using a silica gel column to obtain 21.6 g of compound 241-P4 with a yield of 99%.

2) Preparation of compound 241-P3

Compound 241-P4 (21.6 g, 0.049 mol, 1 eq), (2-bromo-6-(methoxycarbonyl)phenyl)boronic acid (B) (13.3 g, 0.051 mol, 1.05 eq), Pd(PPh3)4 (2.79) g 0.0024 mol, 0.05 eq), K ₂ CO ₃ (16.9 g, 0.121 mol, 2.5 eq), 1,4-dioxane (220 mL), and Water (66 mL) were added and stirred at 100°C for 6 h. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . By separation using a silica gel column, 20 g of compound 241-P3 was obtained with a yield of 66%.

3) Preparation of compound 241-P2

Compound 241-P3 (20 g, 0.035 mol, 1 eq) was added to ThF (200 mL) and stirred. Afterwards, MeMgBr (29 mL, 0.087 mol, 2.5 eq) was added and stirred at 70°C for 3 h. After completion of the reaction, the mixture was added dropwise to HCl (5 mL) and extracted using MC and water. Afterwards, moisture was removed with MgSO ₄ . By separation using a silica gel column, 18.3 g of compound 241-P2 was obtained with a yield of 83%.

4) Preparation of compound 241-P1

Compound 241-P2 (18.3 g, 0.032 mol, 1 eq) was added to DCM (180 mL) and stirred. Afterwards, BF3O(C2H5)2 (3.93 mL, 0.032 mol, 1 eq) was added dropwise and stirred at room temperature for 1 h. After completion of the reaction, NaHCO ₃ aqueous solution (1M, 500 mL) was slowly added. Afterwards, the organic layer was extracted using MC and water, and moisture was removed with MgSO ₄ . Afterwards, it was separated using a silica gel column to obtain 17.5 g of compound 241-P1 with a yield of 90%.

5) Preparation of Compound 241

Compound 241-P1 (10 g, 0.017 mol, 1 eq), phenyl boronic acid (C) (2.34 g, 0.018 mol, 1.05 eq), Pd(PPh ₃ ) ₄ (1.03 g, 0.0009 mol, 0.05 eq), K ₂ CO ₃ (6.19 g, 0.044 mol, 2.5 eq), 1,4-dioxane (100 mL), and Water (30 mL) were added and stirred at 100°C for 6 h. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 9 g of compound 241 was obtained with a yield of 90%.

In Preparation Example 3, intermediate A of Table 3 below was used instead of N-phenylaniline (A), intermediate B was used instead of (2-bromo-6-(methoxycarbonyl)phenyl)boronic acid (B), and intermediate C was used instead of phenyl boronic acid (C). The compound was synthesized using the same method.

compound
number intermediate
A intermediate
B intermediate
C transference number 241 90% 258 72% 275 81% 277 76% 283 86% 290 85% 307 91% 309 88% 326 72% 327 81% 345 77%

[Preparation Example 4] Preparation of compound 356

1) Preparation of compound 356-P4

2-bromo-1-iodo-9,9-dimethyl-9H-fluorene (20 g, 0.05012 mol, 1 eq), N-phenyl-N-(4-phenylphenyl)-4-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A) (23.54 g, 0.05262 mol, 1.05 eq), Pd(PPh ₃ ) ₄ (2.9g 0.00251 mol, 0.05 eq), K ₂ CO ₃ (17.32 g, 0.12529 mol, 2.5 eq), 1,4-dioxane (200 mL), and Water (60 mL) were added and stirred at 100°C for 6 h. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . By separation using a silica gel column, 22 g of compound 356-P4 was obtained with a yield of 74.2%.

2) Preparation of compound 356-P3

Compound 356-P4 (22 g, 0.037 mol, 1 eq), (2-bromo-6-(methoxycarbonyl)phenyl)boronic acid (B) (10.08 g, 0.039 mol, 1.05 eq), Pd(PPh3)4 (2.14) g, 0.0019 mol, 0.05 eq), K ₂ CO ₃ (12.83 g, 0.0927 mol, 2.5 eq), 1,4-dioxane (220 mL), and Water (66 mL) were added and stirred at 100°C for 6 h. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 19.5 g of compound 356-P3 was obtained with a yield of 68.4%.

3) Preparation of compound 356-P2

Compound 356-P3 (19.5 g, 0.0267 mol, 1 eq) was added to ThF (200 mL) and stirred. Afterwards, MeMgBr (22.36 mL, 0.067 mol, 2.5 eq) was added and stirred at 70°C for 3 h. After completion of the reaction, the mixture was added dropwise to HCl (7 mL) and extracted using MC and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 18 g of compound 356-P2 was obtained with a yield of 69%.

4) Preparation of compound 356-P1

Compound 356-P2 (18 g, 0.0247 mol, 1 eq) was added to DCM (240 mL) and stirred. Afterwards, BF ₃ O(C ₂ H5) ₂ (3.52 mL, 0.0247 mol, 1 eq) was added dropwise and stirred at room temperature for 1 h. After completion of the reaction, slowly add NaHCO ₃ aqueous solution (1M, 500 mL). Afterwards, the organic layer was extracted using MC and water, and moisture was removed with MgSO ₄ . Afterwards, it was separated using a silica gel column to obtain 18.9 g of compound 356-P1 with a yield of 80%.

5) Preparation of compound 356

Compound 356-P1 (10 g, 0.0141, 1 eq), dibenzo[b,d]thiophen-4-ylboronic acid (C) (3.38 g, 0.0148 mol, 1.05 eq), K2CO3 (4.87 g 0.035 mol, 2.5 eq) , Pd(PPh ₃ ) ₄ (0.82 g, 0.0007 mol, 0.05 eq), 1,4-dioxane (100 mL), and Water (30 mL) were added and stirred at 100°C for 6 h. After adding water to terminate the reaction, extraction was performed using MC and water. Afterwards, moisture was removed with MgSO ₄ . After separation using a silica gel column, 9 g of compound 356 was obtained with a yield of 78%.

In Preparation Example 4, N-phenyl-N-(4-phenylphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (A) was replaced with Table 4 below. Compounds in the same manner using intermediate A instead of (2-bromo-6-(methoxycarbonyl)phenyl)boronic acid (B), intermediate B, and intermediate C instead of dibenzo[b,d]thiophen-4-ylboronic acid (C). was synthesized.

compound number intermediate
A intermediate
B intermediate
C transference number 356 78% 363 81% 370 79% 389 88% 392 82% 401 75% 407 91% 426 77% 443 86% 450 91% 472 78% 474 82%

[Preparation Example 5] Preparation of compound 483

Compound 022 (5 g, 6.7 mmol) was added to 50 mL of C ₆ D ₆ and purged with nitrogen for 2 hours. 1.5 mL of ethyl aluminum dichloride solution (1.0M in Hexane) was added dropwise through a syringe, and the reaction mixture was heated to reflux for 1 hour. After cooling to room temperature, 50 mL of heavy water was added for extraction, and the organic layer was dried over anhydrous MgSO4 and concentrated using a rotary evaporator. Afterwards, compound 483 (3.8 g, 73%) was obtained through ethylene acetate (EA) slurry.

The target compounds shown in Table 5 below were synthesized in the same manner as in Preparation Example 5, except for the reaction temperature and time described in Preparation Example 5.

compound number reaction temperature reaction time target compound transference number 483 Reflux 1 HR 73% 484 RT 1 HR 80% 505 Reflux 2HR 79% 506 RT 2HR 81% 527 Reflux 4HR 75% 528 RT 4HR 70% 529 Reflux 1 HR 72% 532 RT 2HR 68%

Compounds were prepared in the same manner as in the above preparation examples, and the synthesis confirmation results are shown in Tables 6 and 7 below. Table 6 shows the measured values of ¹ H NMR (DMSO, 300 MHz), and Table 7 shows the measured values of FD-MS (Field desorption mass spectrometry).

compound ¹ H NMR (DMSO, 300 MHz) 001 8.24(1H, d), 7.98(1H, s), 7.74(1H,d), 7.57~7.38(7H, m), 7.24~7.16(7H, m), 7.08~7.00(6H, m), 1.69( 12H, s) 007 8.24(1H, d), 8.09~8.06(2H, d), 7.99~7.98(2H, m), 7.75~7.74(5H, d), 7.63~7.37(22H, m), 7.06(1H, d), 1.69(12H, s) 024 8.24(1H, d), 8.08~7.98(4H, m), 7.90~7.86(5H, d), 7.74(1H, d), 7.57~7.51(5H, m), 7.39~7.28(10H, m), 7.16(3H, d), 1.69(24H, s) 031 8.45(1H, d), 8.24~8.17(4H, m), 7.98~7.86(4H, m), 7.75~7.74(3H, d), 7.57~7.27(15H, m), 7.18~7.16(3H, d) ), 7.06(1H, d), 1.69(18H, s) 043 8.24(1H, d), 7.98(2H, m), 7.75~7.74(3H, d), 7.57~7.16(22H, m), 6.97(1H, d), 1.69(12H, s) 050 8.45(1H, d), 8.24(1H, d), 8.11~8.06(4H, d), 7.99~7.93(3H, m), 7.74(1H, d), 7.63~7.38(17H, m), 7.14~ 7.06(4H, m), 1.69(12H, s) 067 8.24(1H, d), 8.08~7.98(6H, m), 7.90~7.82(4H, d), 7.76(2H, s), 7.57~7.51(7H, m), 7.39~7.28(11H, m), 7.16(2H, d), 1.69(18H, s) 074 8.45(2H, d), 8.24(1H, d), 8.12~8.11(3H, d), 7.99~7.86(6H, m), 7.74(1H, d), 7.57~7.28(14H, m), 7.16( 1H, d), 7.06(1H, d), 1.69(18H, s) 082 8.24(1H, d), 8.09~8.06(2H, d), 7.99~7.98(2H, m), 7.78~7.71(5H, d), 7.62~7.37(19H, m), 7.11~7.06(2H, d) ), 1.69(12H, s) 083 8.24~8.22(2H, d), 8.15(2H, d), 8.03~7.98(3H, m), 7.90~7.74(7H, d), 7.63~7.49(7H, m), 7.39~7.28(7H, m) ), 7.16(2H, d), 1.69(18H, s) 084 8.55(1H, d), 8.45(1H, d), 8.32(1H, d), 8.24(1H, d), 7.98~7.86(4H, m), 7.78~7.70(4H, m), 7.57~7.28( 14H, m), 7.16~7.06(3H, d), 1.69(18H, s) 086 8.24(1H, d), 7.98(1H, s), 7.78~7.71(5H, d), 7.57~7.37(17H, m), 7.24~7.11(4H, m), 1.69(12H, s) 098 8.24(1H, d), 8.10~8.06(3H, d), 7.99~7.98(2H, m), 7.90~7.86(2H, m), 7.74(1H, d), 7.63~7.51(7H, m), 7.43~7.06(25H, m), 1.69(12H, s) 100 8.55(1H, d), 8.45(1H, d), 8.32(1H, d), 8.24(1H, d), 7.98~7.85(6H, m), 7.75~7.70(4H, m), 7.57~7.28( 23H, m), 7.06(2H, d), 1.69(12H, s) 104 8.24(1H, d), 8.08~7.98(4H, m), 7.90~7.85(5H, d), 7.75~7.74(3H, d), 7.57~7.23(24H, m), 7.16(1H, d), 7.06(1H, d), 1.69(12H, s) 111 8.45(1H, d), 8.24~8.17(4H, d), 7.98~7.86(4H, m), 7.75~7.74(3H, d), 7.57~7.06(29H, m), 1.69(12H, s) 123 8.24(1H, d), 7.98(1H, s), 7.78~7.74(2H, d), 7.65(1H, d),7.57~7.37(12H, m), 7.24(4H, t), 7.08~7.00( 6H, m), 1.69(12H, s) 135 8.95(1H, d), 8.50(1H, d), 8.24~8.18(3H, m), 8.10~8.09(2H, d), 7.98(1H, s), 7.90~7.86(2H, d), 7.77~ 7.68(4H, m), 7.57~7.52(5H, m), 7.43~7.28(12H, m), 7.16~7.08(4H, m), 1.69(18H, s) 147 8.24(1H, d), 8.09~7.98(5H, m), 7.89(1H, s), 7.82~7.74(6H, d), 7.57~7.28(21H, m), 6.97(1H, d), 1.69( 12H, s) 154 8.45(1H, d), 8.24(1H, d), 8.12(2H, m), 8.00~7.86(8H, m), 7.74(1H, d), 7.68(1H, d), 7.57~7.49(8H, m), 7.38~7.28(9H, m), 7.16(2H, d) 1.69(24H, s) 162 8.24(1H, d), 8.18(1H, d), 8.09~7.98(7H, m), 7.75~7.31(30H, m), 1.69(12H, s) 171 8.45(1H, d), 8.24(1H, d), 8.11(1H, d), 7.98~7.93(2H, m), 7.78~7.74(4H, d), 7.65(1H, d), 7.57~7.37( 23H, m), 1.69(12H, s) 191 8.45(1H, d), 8.24~8.17(4H, m), 8.00~7.86(6H, m), 7.74~7.49(11H, m), 7.39~7.28(9H, m), 7.16(1H, d), 6.97(1H, d), 1.69(18H, s) 200 8.24(1H, d), 8.09~7.98(5H, m), 7.89(1H, s), 7.78~7.71(6H, d), 7.57~7.31(21H, m), 7.11(1H, s), 1.69( 12H, s) 204 8.24(1H, d), 8.09~8.06(2H, d), 7.99~7.98(2H, m), 7.78~7.37(29H, m), 7.11(1H, s), 1.69(12H, s) 214 8.24(1H, d), 7.98(1H, s), 7.90~7.86(2H, d), 7.78~7.65(5H, d), 7.57~7.33(20H, m), 7.16~7.11(2H, d), 1.69(18H, s) 227 8.24(1H, d), 8.10~7.98(5H, m), 7.90~7.74(9H, m), 7.57~7.54(6H, m), 7.43~7.23(18H, m), 7.14~7.06(4H, m) ), 1.69(12H, s) 239 8.45(1H, d), 8.24~8.17(4H, m), 8.10(1H, d), 8.00~7.85(7H,m), 7.74~7.68(2H, d), 7.57~7.37(19H, m), 7.28~7.23(5H, m), 7.14~7.06(4H, m), 1.69(12H, s) 241 8.24(1H, d), 7.79~7.74(4H, d), 7.65(1H, d), 7.57~7.54(2H, m), 7.47~7.38(5H, m), 7.24(4H, t), 7.08~ 7.00(6H, m), 1.69(12H, s) 258 8.24(1H, t), 8.10~8.06(3H, d), 7.96~7.90(2H, d), 7.78~7.74(2H, d), 7.65~7.55(7H, m), 7.47~7.28(11H, m) ), 7.16~7.08(4H, m), 1.69(18H, s) 275 8.24(1H, d), 8.03~7.98(3H, d), 7.82~7.74(5H, d), 7.65~7.27(18H, m), 7.18~7.17(2H, d), 6.97(1H, d), 1.69(12H, s) 277 8.45(1H, d), 8.24(1H, d), 8.18(1H, d), 8.03~7.93(4H, d), 7.75~7.31(23H, m), 6.97(1H, d), 1.69(12H, s) 283 8.24(1H, d), 8.09(1H, d), 7.98(1H, d), 7.89(1H, s), 7.78~7.74(6H, d), 7.64~7.27(16H, m), 7.18~7.17( 2H, d), 6.97(1H, d), 1.69(12H, s) 290 8.45(1H, d), 8.24(1H, d), 8.11~8.06(4H, m), 7.99~7.93(2H, d), 7.78~7.74(2H, d), 7.65~7.37(18H, m), 7.14~7.08(3H, m), 1.69(12H, s) 307 8.24(1H, d), 8.08~7.98(5H, d), 7.90~7.74(6H, m), 7.65(1H, d), 7.57~7.47(9H, m), 7.39~7.28(10H, m), 7.16(1H, d) 1.69(18H.s) 309 8.45(1H, d), 8.24(1H, d), 8.18(1H, s), 7.98~7.86(6H,m), 7.74~7.49(11H, m), 7.39~7.28(7H, m), 7.16( 1H, d), 6.97(1H, d), 1.69(18H, s) 326 8.24(1H, d), 8.18(1H, s), 7.78~7.68(9H, m), 7.57~7.37(17H, m), 7.11(1H, s), 1.69(12H, s) 327 8.95(1H, d), 8.50(1H, d), 8.24~8.09(6H, m), 7.90~7.49(15H, m), 7.39~7.28(5H, m), 7.16(1H, d), 1.69( 18H, s) 345 8.24(1H, d), 8.09(1H, d), 7.98(1H, d), 7.90~7.69(9H, m), 7.57~7.10(29H, m), 1.69(12H, s) 356 8.55(1H, d), 8.45(1H, d), 8.32(1H, d), 8.24(1H, d), 7.98~7.93(2H, m), 7.78~7.65(6H, m), 7.57~7.37( 16H, m), 7.24(2H, t), 7.08~7.00(3H, m), 1.69(12H, s) 363 8.24(1H, d), 8.09(1H, d), 7.98(1H, s), 7.89(1H, s), 7.78~7.74(4H, d), 7.55~7.37(9H, m), 7.24(4H, t), 7.08~7.00(6H, m), 1.69(12H, s) 370 8.24(1H, d), 8.10~8.06(3H, d), 7.99~7.98(2H, m), 7.78~7.74(4H, d), 7.65~7.37(22H, m), 7.14~7.08(3H, m) ), 1.69(12H, s) 389 8.45(1H, d), 8.24(1H, d), 8.18(1H, s), 8.03~7.86(6H, m), 7.75~7.68(6H, m), 7.57~7.27(17H, m), 7.18~ 7.16(3H, d), 1.69(18H, s) 392 8.24(1H, d), 8.18(1H, s), 8.10~7.98(6H, m), 7.74~7.28(22H, m), 7.14~7.08(3H, m), 6.97(1H, d), 1.69( 12H, s) 401 8.24(1H, d), 7.98(2H, m), 7.79~7.74(6H, m), 7.57~7.28(21H, m), 7.18~7.17(2H, d), 6.97(1H, d), 1.69( 12H, s) 407 8.95(1H, d), 8.50~8.45(2H, d), 8.24~8.18(3H, m), 8.11~8.09(2H, d), 7.98~7.93(2H, m), 7.77~7.68(6H, m) ), 7.57~7.37(19H, m), 1.69(12H, s) 426 8.55(1H, d), 8.45(2H, d), 8.32(1H, d), 8.24(1H, d),8.12~8.09(3H, d), 7.99~7.89(5H, m), 7.78~7.70( 5H, m), 7.57~7.37(21H, m), 1.69(12H, s) 443 8.24~8.22(2H, d), 8.15~8.09(2H, d), 7.98(1H, s), 7.89(1H, s), 7.81~7.74(7H, m), 7.63~7.37(20H, m), 1.69(12H, s) 450 8.24(1H, d), 8.09~8.06(2H, d), 7.99~7.98(2H, m), 7.90~7.86(2H, d), 7.78~7.28(24H, m), 7.16~7.11(2H, m) ), 1.69(18H, s) 472 8.24(1H, d), 8.18(1H, s), 8.08~7.98(4H, m), 7.90~7.85(4H, d), 7.75~7.68(5H, d), 7.57~7.27(25H, m), 7.06(1H, d), 1.69(12H, s) 474 8.45(1H, d), 8.24(1H, d), 8.12~8.09(3H, d), 7.98~7.85(8H, m), 7.78~7.74(4H, d), 7.57~7.37(20H, m), 7.28~7.23(5H, m), 7.06(1H, d), 1.69(6H, s) 483 All D substituents 484 8.10(1H, d), 7.90~7.86(2H, d), 7.55(1H, d), 7.43~7.28(8H, m), 7.15~7.08(4H, m), 1.69(6H, s) 505 All D substituents 506 8.95(1H, d), 8.50(1H, d), 8.24~8.20(2H, d), 8.09(1H, d), 8.00(1H, d), 7.77~7.68(3H, m), 7.57~7.52( 4H, m), 7.39~7.38(2H, t), 1.69(12H, s) 527 All D substituents 528 8.22~8.15(2H, d), 7.81~7.75(3H, d), 7.63~7.37(11H, m) 529 7.90~7.86(4H, d), 7.75(2H, d), 7.55~7.16(23H,m) 532 8.24(1H, d), 8.09(1H, d), 7.98(1H, s), 7.90~7.86(3H, m), 7.78~7.74(4H, d), 7.57~7.10(28H, m), 1.69( 12H, s)

compound FD-MS compound FD-MS 001 m/z=553.28
(C42H35N =553.75) 007 m/z=755.36
(C58H45N =756.00) 024 m/z=875.41
(C66H53NO =876.16) 031 m/z=851.36
(C63H49NS =852.15) 043 m/z=719.32 (C54H41NO=719.93) 050 m/z=785.31 (C58H43NS = 786.05) 067 m/z=925.39 (C69H51NO2 =926.17) 074 m/z=881.31 (C63H47NS2 =882.20) 082 m/z= 729.34 (C56H43N =729.97) 083 m/z=809.37 (C61H47NO
= 810.05) 084 m/z=825.34 (C61H47NS = 826.11) 086 m/z=679.32 (C52H41N =679.91) 098 m/z=919.42 (C71H53N =920.21) 100 m/z=973.37 (C73H51NS = 974.28) 104 m/z=957.40 (C73H51NO=958.22) 111 m/z = 975.39 (C73H53NS = 976.29) 123 m/z=629.31 (C48H39N = 629.85) 135 m/z=871.42 (C67H53N =872.17) 147 m/z=885.36 (C66H47NO2 =886.11) 154 m/z=967.42(C72H57NS=968.31) 162 m/z=921.40 (C70H51NO=922.18) 171 m/z=811.33(C63H49NO=812.09) 191 m/z=941.37(C69H51NOS=942.23) 200 m/z=845.37(C64H47NO=846.09) 204 m/z=805.37 (C62H47N=806.06) 214 m/z=795.39(C61H49N=796.07) 227 m/z=1033.43(C79H55NO=1034.31) 239 m/z=1049.41(C79H55NS=1050.38) 241 m/z=553.28(C42H35N=553.75) 258 m/z=795.39(C61H49N=796.07) 275 m/z=809.33 (C60H43NO2=810.01) 277 m/z=825.31(C60H43NOS=826.07) 283 m/z=719.32(C54H41NO=719.93) 290 m/z=785.31 (C58H43NS = 786.05) 307 m/z=925.39(C69H51NO2=926.17) 309 m/z=865.34(C63H47NOS=866.13) 326 m/z=679.32(C52H41N=679.91) 327 m/z=769.37(C59H47N=770.03) 345 m/z=959.41(C73H53NO=960.23) 356 m/z = 811.33 (C60H45NS = 812.09) 363 m/z=629.31 (C48H39N = 629.85) 370 m/z=831.39(C64H49N=832.10) 389 m/z = 927.39 (C69H53NS = 928.25) 392 m/z=885.36(C66H47NO2=886.11) 401 m/z=795.35(C60H45NO=796.03) 407 m/z=861.34(C64H47NS=862.15) 426 m/z=993.35(C72H51NS2=994.33) 443 m/z=755.36(C58H45N=756.00) 450 m/z=845.40(C65H51N=846.13) 472 m/z=1033.43(C79H55NO=1034.31) 474 m/z=1049.41(C79H55NS=1050.38) 483 m/z=792.67(C57D47N=793.30) 484 m/z=770.53(C57H22D25N=771.16) 505 m/z=640.52(C46D37N=641.03) 506 m/z=613.36 (C46H27D10N = 613.87) 527 m/z=800.64(C58D45N=801.28) 528 m/z=784.54 (C58H16D29N = 785.18) 529 m/z=887.51
(C67H29D20N = 888.26) 532 m/z=1042.49
(C79H50D7NO = 1043.37)

[Experimental example]

<Experimental Example 1>

1) Fabrication of organic light emitting device

The transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung-Corning) was ultrasonically cleaned for 5 minutes each using trichlorethylene, acetone, ethanol, and distilled water sequentially, and then stored in isopropanol before use. Next, the ITO substrate was installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.

Subsequently, the vacuum in the chamber was evacuated until it reached 10 ^-6 torr, and then a current was applied to the cell to evaporate 2-TNATA and deposit a hole injection layer with a thickness of 600 Å on the ITO substrate. In another cell in the vacuum deposition equipment, the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (N,N'-bis(α-naphthyl)-N, N'-diphenyl-4,4'-diamine: NPB) was added and evaporated by applying a current to the cell to deposit a 300 Å thick hole transport layer on the hole injection layer.

After forming the hole injection layer and the hole transport layer in this way, a blue light-emitting material with the following structure was deposited on it as a light-emitting layer. Specifically, H1, a blue light-emitting host material, was vacuum-deposited to a thickness of 200 Å in one cell of the vacuum deposition equipment, and D1, a blue light-emitting dopant material, was vacuum-deposited 5% of the host material on top of it.

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

Lithium fluoride (LiF) was deposited to a thickness of 10 Å as an electron injection layer, and an OLED device was manufactured with an Al cathode to a thickness of 1,000 Å. Meanwhile, all organic compounds required for OLED device production were purified by vacuum sublimation under 10 ^-6 to 10 ^-8 torr for each material and used for OLED production. An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that the compounds shown in Table 8 below were used instead of NPB used in forming the hole transport layer in Experiment 1. The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured using M7000 from McScience, and the standard luminance was measured at 700 cd/ through a lifespan measuring device (M6000) manufactured by McScience based on the measurement results. When m ² , T ₉₅ was measured. Table 8 shows the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the blue organic light-emitting device manufactured according to the present invention.

compound driving voltage
(V) Luminous efficiency
(cd/A) CIE
(x, y) life span
(T ₉₅ ) Example 1 001 4.90 6.86 (0.134, 0.100) 90 Example 2 024 4.81 6.85 (0.133, 0.101) 92 Example 3 031 4.83 6.81 (0.133, 0.100) 91 Example 4 050 4.83 6.81 (0.134, 0.101) 89 Example 5 074 4.86 6.79 (0.133, 0.101) 81 Example 6 082 4.80 6.82 (0.133, 0.101) 83 Example 7 084 4.86 6.84 (0.133, 0.100) 84 Example 8 086 4.90 6.86 (0.133, 0.100) 86 Example 9 100 4.88 6.79 (0.133, 0.101) 88 Example 10 111 4.90 6.91 (0.133, 0.100) 84 Example 11 135 4.84 6.90 (0.133, 0.100) 89 Example 12 147 4.82 6.90 (0.134, 0.101) 83 Example 13 171 4.81 6.88 (0.133, 0.101) 85 Example 14 191 4.91 6.79 (0.134, 0.100) 86 Example 15 214 4.86 6.86 (0.133, 0.101) 87 Example 16 239 4.83 6.81 (0.134, 0.100) 89 Example 17 241 4.83 6.86 (0.134, 0.100) 90 Example 18 258 4.84 6.84 (0.133, 0.100) 88 Example 19 275 4.81 6.86 (0.133, 0.101) 90 Example 20 283 4.89 6.89 (0.133, 0.101) 86 Example 21 290 4.81 6.90 (0.133, 0.100) 88 Example 22 307 4.85 6.90 (0.133, 0.100) 81 Example 23 327 4.90 6.89 (0.133, 0.101) 89 Example 24 345 4.85 6.79 (0.134, 0.101) 84 Example 25 363 4.81 6.86 (0.134, 0.100) 83 Example 26 392 4.83 6.86 (0.134, 0.101) 87 Example 27 407 4.83 6.91 (0.134, 0.100) 81 Example 28 426 4.84 6.90 (0.134, 0.101) 86 Example 29 450 4.86 6.89 (0.134, 0.100) 90 Example 30 472 4.81 6.89 (0.134, 0.100) 91 Example 31 483 4.88 6.84 (0.133, 0.100) 93 Example 32 484 4.90 6.88 (0.134, 0.100) 87 Example 33 505 4.88 6.81 (0.133, 0.100) 91 Example 34 506 4.89 6.89 (0.134, 0.101) 95 Example 35 529 4.87 6.82 (0.134, 0.101) 93 Comparative Example 1 NPB 5.54 6.05 (0.134, 0.100) 52 Comparative Example 2 Comparative compound A 5.33 6.31 (0.133, 0.100) 53 Comparative Example 3 Comparative compound B 5.30 6.36 (0.133, 0.100) 52 Comparative Example 4 Comparative compound C 5.22 6.40 (0.134, 0.101) 51 Comparative Example 5 Comparative compound D 5.36 6.39 (0.134, 0.100) 49 Comparative Example 6 Comparative compound E 5.35 6.36 (0.133, 0.100) 53 Comparative Example 7 Comparative compound F 5.29 6.35 (0.134, 0.101) 54

As can be seen from the results in Table 8, the organic light emitting device using the hole transport layer material of the blue organic light emitting device of the present invention had a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 1 to 7. In the case of Comparative Examples 2 and 4, although they have an asymmetric two-substituent structure, the substituents are located in the ring at both ends or the middle ring, so electron and hole mobility suitable for the device used in the present invention cannot be realized, and Comparative Examples 3 and 5 In this case, it is difficult to form structures of various shapes with a single-substituent structure, so it is difficult to control appropriate physical and chemical properties depending on the device. Comparative Examples 1 and 6 to 7 have a symmetric structure, so it is difficult to form a uniform film when manufacturing a hole transport layer. There is a disadvantage that it is not easy to use and the device characteristics may be significantly deteriorated.

Therefore, in the case of the compound presented in the present invention, when forming a hole transport layer with an asymmetrical two-substituent structure in which substituents such as amine groups and aryl groups are used simultaneously, crystallinity is appropriate and a film can be effectively formed, and the bonded substituents are combined properly. It is believed that this is because electron and hole mobility is realized at a speed appropriate for the device due to length and strength, forming a more stable compound, and electrons can be transferred efficiently without decomposition or destruction of the compound. thus. It is believed that the compound of the present invention has improved electron-transport properties or improved stability, resulting in excellence in all aspects of operation, efficiency, and lifespan.

<Experimental Example 2>

1) Fabrication of organic light emitting device

The transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung-Corning) was ultrasonically cleaned for 5 minutes each using trichlorethylene, acetone, ethanol, and distilled water sequentially, and then stored in isopropanol before use. Next, the ITO substrate was installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine ( 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2-TNATA) was added.

Subsequently, the vacuum in the chamber was evacuated until it reached 10 ^-6 torr, and then a current was applied to the cell to evaporate 2-TNATA and deposit a hole injection layer with a thickness of 600 Å on the ITO substrate. In another cell in the vacuum deposition equipment, the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (N,N'-bis(α-naphthyl)-N, N'-diphenyl-4,4'-diamine: NPB) was added and evaporated by applying a current to the cell to deposit a 300 Å thick hole transport layer on the hole injection layer.

After forming the hole injection layer and the hole transport layer in this way, a blue light-emitting material with the following structure was deposited as a light-emitting layer thereon. Specifically, H1, a blue light-emitting host material, was vacuum-deposited to a thickness of 200 Å in one cell of the vacuum deposition equipment, and D1, a blue light-emitting dopant material, was vacuum-deposited 5% of the host material on top of it.

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

Lithium fluoride (LiF) was deposited to a thickness of 10 Å as an electron injection layer, and an OLED device was manufactured with an Al cathode to a thickness of 1,000 Å. Meanwhile, all organic compounds required for OLED device production were purified by vacuum sublimation under 10 ^-6 to 10 ^-8 torr for each material and used for OLED production. In Experimental Example 2, the hole transport layer NPB was formed at a thickness of 250 Å, and then an electron blocking layer of the compound shown in Table 9 below was formed at a thickness of 50 Å on top of the hole transport layer. It was the same as Experiment 2. An organic electroluminescent device was manufactured by performing this procedure. Table 9 shows the results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the blue organic light-emitting device manufactured according to the present invention.

compound driving voltage
(V) Luminous efficiency
(cd/A) CIE
(x, y) life span
(T ₉₅ ) Example 36 001 4.88 6.89 (0.133,0.100) 91 Example 37 024 4.90 6.86 (0.134,0.101) 93 Example 38 031 4.81 6.90 (0.133,0.100) 90 Example 39 050 4.86 6.90 (0.133,0.101) 88 Example 40 074 4.89 6.89 (0.133,0.101) 88 Example 41 083 4.87 6.82 (0.133,0.100) 85 Example 42 086 4.91 6.81 (0.134,0.100) 81 Example 43 098 4.88 6.84 (0.133,0.100) 83 Example 44 104 4.85 6.82 (0.133,0.100) 83 Example 45 111 4.81 6.86 (0.133,0.100) 91 Example 46 135 4.79 6.88 (0.134,0.100) 83 Example 47 147 4.91 6.91 (0.133,0.100) 92 Example 48 171 4.90 6.83 (0.133,0.100) 88 Example 49 191 4.83 6.86 (0.133,0.101) 87 Example 50 214 4.81 6.88 (0.133,0.101) 83 Example 51 239 4.86 6.90 (0.134,0.100) 82 Example 52 241 4.89 6.85 (0.133,0.101) 81 Example 53 258 4.84 6.87 (0.133,0.100) 83 Example 54 275 4.85 6.88 (0.134,0.100) 88 Example 55 283 4.90 6.83 (0.134,0.101) 91 Example 56 290 4.86 6.85 (0.133,0.101) 83 Example 57 307 4.81 6.84 (0.134,0.100) 80 Example 58 327 4.81 6.90 (0.133,0.100) 88 Example 59 345 4.91 6.91 (0.133,0.101) 87 Example 60 363 4.86 6.79 (0.134,0.100) 84 Example 61 392 4.93 6.88 (0.134,0.100) 83 Example 62 407 4.79 6.87 (0.133,0.101) 90 Example 63 450 4.81 6.90 (0.134,0.100) 81 Example 64 472 4.83 6.89 (0.133,0.100) 90 Example 65 483 4.87 6.87 (0.133,0.101) 93 Example 66 484 4.81 6.83 (0.133,0.100) 88 Example 67 505 4.90 6.82 (0.133,0.100) 91 Example 68 506 4.91 6.85 (0.133,0.100) 93 Example 69 532 4.88 6.81 (0.133,0.100) 92 Comparative Example 8 NPB 5.55 6.07 (0.134,0.100) 53 Comparative Example 9 Comparative compound A 5.34 6.19 (0.134,0.100) 51 Comparative Example 10 Comparative compound B 5.36 6.20 (0.133,0.101) 53 Comparative Example 11 Comparative compound C 5.34 6.16 (0.134,0.101) 57 Comparative Example 12 Comparative compound D 5.37 6.19 (0.134,0.101) 54 Comparative Example 13 Comparative compound E 5.31 6.11 (0.133,0.101) 60 Comparative Example 14 Comparative compound F 5.33 6.09 (0.133,0.101) 56

As can be seen from the results in Table 9, the organic light emitting device using the electron blocking layer material of the blue organic light emitting device of the present invention had a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Examples 8 to 14. In Comparative Examples 9 and 12, it is difficult to form various types of structures with a single-substituent structure, making it difficult to implement appropriate characteristics depending on the device, and in Comparative Examples 10 to 11, although it is an asymmetrical two-substituent structure, rings at both ends or the center In the form of a substituent located on the ring, electron and hole mobility suitable for the device used in the present invention cannot be realized, and in Comparative Examples 13 to 14, when the electron blocking layer is manufactured with a symmetric structure, the crystallinity is too high to form a uniform film. It has the disadvantage that it is not easy to form and the device characteristics may be significantly deteriorated.

Therefore, in the case of the compound presented in the present invention, when forming an electron blocking layer with an asymmetrical two-substituent structure in which substituents such as an amine group and an aryl group are used simultaneously, crystallinity is appropriate and an effective film can be formed. Additionally, in the case of electrons, if they are not combined in the light emitting layer and pass through the hole transport layer to the anode, there is a problem of reducing the efficiency and lifespan of the OLED device. To prevent this phenomenon, if a compound with a high LUMO level and T1 level is used as an electron blocking layer, the probability that electrons trying to pass through the light-emitting layer to the anode will form an exciton in the light-emitting layer increases. As a result, it is judged that the compound of the present invention is superior in all aspects of operation, efficiency, and lifespan.

100: substrate
200: anode
300: Organic layer
301: Hole injection layer
302: Hole transport layer
303: light emitting layer
304: Electron transport layer
305: Electron injection layer
400: cathode

Claims (15)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group,
One of Z1 and Z2 is -NAr1Ar2, and the other is a substituted or unsubstituted aryl group of C6 to C60; Or a substituted or unsubstituted C2 to C60 heteroaryl group,
Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C60; Substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof,
R1 to R3 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen; Substituted or unsubstituted C1 to C60 alkyl group; Substituted or unsubstituted C2 to C60 alkenyl group; Substituted or unsubstituted C2 to C60 alkynyl group; Substituted or unsubstituted C1 to C60 alkoxy group; Substituted or unsubstituted C3 to C60 cycloalkyl group; Substituted or unsubstituted C2 to C60 heterocycloalkyl group; Substituted or unsubstituted C6 to C60 aryl group; Substituted or unsubstituted C2 to C60 heteroaryl group; -SiRR'R"; and -P(=O)RR'; or adjacent groups of R1 to R3 combine to form a ring,
R, R' and R" are the same or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted A substituted or unsubstituted C2 to C60 heteroaryl group;
m1 and p1 are the same or different from each other and are each independently an integer from 0 to 4,
n1 and q1 are the same or different from each other and are each independently an integer of 1 to 4,
a is an integer from 0 to 4,
b is an integer from 0 to 3,
When each of a, b, m1, n1, p1 and q1 is 2 or more, each of R1, R2, L1, L2, Z1 and Z2 are the same or different from each other. In claim 1,
Formula 1 is a compound represented by any one of the following formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
L1, L2, Z1, Z2, R1 to R3, a, b, m1, n1, p1 and q1 are the same as defined in Formula 1 above. In claim 1,
wherein L1 and L2 are the same or different from each other and are each independently directly bonded; Or a compound that is a substituted or unsubstituted C6 to C30 arylene group. In claim 1,
Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C30 aryl group; Substituted or unsubstituted C2 to C30 heteroaryl group; Or a compound that is a combination thereof. In claim 1,
The compound represented by Formula 1 is a compound represented by Formula 2 or 3 below:
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
Each of R1 to R3, L1, Z1, L2, Z2, Ar1, Ar2, a, b, m1, n1, p1 and q1 is the same as defined in Formula 1 above. In claim 5,
The compound represented by Formula 2 is a compound represented by any one of the following Formulas 2-1 to 2-4:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,
Each of R1 to R3, L1, L2, Z2, Ar1, Ar2, a, b, m1, p1 and q1 is the same as defined in Formula 1 above. In claim 5,
The compound represented by Formula 3 is a compound represented by any one of the following Formulas 3-1 to 3-4:
[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

In Formulas 3-1 to 3-4,
Each of R1 to R3, L1, Z1, L2, Ar1, Ar2, a, b, m1, n1 and p1 is the same as defined in Formula 1 above. In claim 1,
-NAr1Ar2 of Formula 1 is a compound represented by any one of the following structural formulas A, B, and C:
[Structural Formula A]

[Structural Formula B]

[Structural Formula C]

In the structural formulas A, B and C,
X1 is O, S, or NRa;
Ra is a substituted or unsubstituted C1 to C30 alkyl group; Or a substituted or unsubstituted aryl group of C6 to C30,
L33 and L44 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6 to C30 arylene group; Or a substituted or unsubstituted C2 to C30 heteroarylene group,
Ar33 and Ar44 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group of C6 to C30,
R4 and R5 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C6 to C30 aryl group; is selected from the group consisting of a substituted or unsubstituted C2 to C30 heteroaryl group, or the adjacent groups of R4 and R5 combine to form a ring,
d is an integer from 0 to 8,
e is an integer from 0 to 7,
When each d and e is 2 or more, each R4 and R5 are the same or different from each other. In claim 1,
R1 to R3 are the same as or different from each other, and are each independently hydrogen; Or a compound that is deuterium. In claim 1,
The deuterium content of the compound of Formula 1 is 0%, or 1% to 100%. In claim 1,
Formula 1 is a compound represented by any one of the following compounds:















































































. first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 11. Light-emitting device. In claim 12,
The organic material layer includes a hole transport layer (Host transfer layer: HTL), a hole transport auxiliary layer (Prime HTL), and an electron blocking layer (EBL), and at least one of the hole transport layer, the hole transport auxiliary layer, and the electron blocking layer One is an organic light-emitting device comprising a compound represented by Formula 1 above. In claim 12,
The organic light emitting device further includes one or two layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. In claim 12,
The organic light-emitting device includes a first electrode, a first stack provided on the first electrode and including a first stack light-emitting layer, a charge generation layer provided on the first stack, and a first stack provided on the charge generation layer. An organic light emitting device comprising a second stack including a two-stack light emitting layer, and a second electrode provided on the second stack.