KR102655897B1 - Condensed multicyclic compound and organic light emitting device comprising same - Google Patents

Abstract

This specification relates to a condensed polycyclic compound of Formula 1 and an organic light-emitting device containing the same.

Description

Condensed polycyclic compound and organic light-emitting device containing the same {CONDENSED MULTICYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

This specification relates to condensed polycyclic compounds and organic light-emitting devices containing the same.

Electroluminescent devices are a type of self-luminous display devices and have the advantages 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 disappear, emitting light. The organic thin film may be composed of a single layer or multiple layers, depending on need.

The material of the organic thin film may have a light-emitting function as needed. For example, as an organic thin film material, a compound that can independently form a light-emitting layer may be used, or a compound that can act as a host or dopant of a host-dopant-based light-emitting layer may be used. In addition, as a material for the organic thin film, compounds that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

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

US Patent No. 4,356,429

The present specification is intended to provide a condensed polycyclic compound and an organic light-emitting device containing the same.

In one embodiment of the present specification, a condensed polycyclic compound of the following formula (1) is provided.

[Formula 1]

In Formula 1,

R1 to R12 are each independently hydrogen; heavy hydrogen; halogen group; -CN; -SiRR'R"; -NRR'; -P(=O)RR'; Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; Substituted or unsubstituted carbon number Alkynyl group of 2 to 60 carbon atoms; Substituted or unsubstituted alkoxy group of 1 to 60 carbon atoms; Substituted or unsubstituted aryloxy group of 6 to 60 carbon atoms; Substituted or unsubstituted alkylthioxy group of 1 to 60 carbon atoms; Substituted or Unsubstituted arylthioxy group having 6 to 60 carbon atoms; Substituted or unsubstituted alkylsulfoxy group having 1 to 60 carbon atoms; Substituted or unsubstituted arylsulfoxy group having 6 to 60 carbon atoms; Substituted or unsubstituted arylsulfoxy group having 3 to 60 carbon atoms A cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

R, R' and R" are each independently hydrogen; deuterium; halogen group; -CN; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

At least one of R1 to R12 is -NRR'; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In another embodiment of the present specification, a first electrode; An organic light-emitting device comprising a second electrode and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes one or more types of the condensed polycyclic compound. provides.

When used in an organic light-emitting device, the condensed polycyclic compound described herein can lower the driving voltage of the device, improve luminous efficiency, and improve the lifespan characteristics of the device. Specifically, the condensed polycyclic compound of the present invention has a core structure in which three benzene rings are condensed with cycloheptene, and is characterized in that an amine group or an azine group is bonded to the core structure through a linker.

When having an amine group as a substituent, hole mobility increases due to the high HOMO level and has an electron blocking effect, which has the effect of lowering the driving voltage when used as a material for a hole transport layer, and when used as a material for a light emitting layer, Efficiency is improved through reduction of current leakage and electron confinement effect.

The compound having an azine group as a substituent has excellent electron transport ability, and when used in combination with the compound having an amine group as a substituent of the present invention as a material for the light emitting layer, the exciplex phenomenon occurs, which lowers the driving voltage and improves the lifespan. There is.

1 to 3 are diagrams illustrating exemplary stacked structures of organic light-emitting devices according to an exemplary embodiment of the present specification.

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.

는 결합되는 위치를 의미한다.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; -SiRR'R"; -P(=O)RR'; means that one or more substituents selected from the group consisting of -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, “when 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 /T1×100 = T%.

로 표시되는 페닐기에 있어 중수소의 함량 20%라는 것은 페닐기가 가질 수 있는 치환기의 총 개수는 5(식 중 T1)개이고, 그 중 중수소의 개수가 1(식 중 T2)인 경우 20%로 표시될 수 있다. 즉, 페닐기에 있어 중수소의 함량이 20%인 것은 하기 구조식으로 표시될 수 있다.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, the 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 carbon number of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. 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.

,

,

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

It may be, but is not limited to this.

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 pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, and thiazolyl group. group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , thiazinyl group, deoxynyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyryl group, naphthyridyl group, acridinyl group, phenanthridide Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group , dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirobi (dibenzosilol), dihydrophenazinyl group, Phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10, 11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 2,3-dihydrobenzo[b]thiophene, 2,3-dihydrobenzofuran, 5,10-dihydrodibenzo[b,e ][1,4]azacylinyl, pyrazolo[1,5-c]quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1, Examples include, but are not limited to, 2-e]indolinyl group and 5,11-dihydroindeno[1,2-b]carbazolyl group.

(트리메틸실릴기),

(트리에틸실릴기),

(t-부틸디메틸실릴기),

(비닐디메틸실릴기),

(프로필디메틸실릴기),

(트리페닐실릴기),

(디페닐실릴기),

(페닐실릴기) 등이 있으나, 이에 한정되는 것은 아니다.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 fluorescein 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 at 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 each of the above-described cycloalkyl groups and aryl groups, except that they are not monovalent. Structures exemplified by groups, heterocycloalkyl groups, and heteroaryl groups can be applied.

An exemplary embodiment of the present specification provides a condensed polycyclic compound of Formula 1 above.

In an exemplary embodiment of the present specification, R1 to R12 in Formula 1 are each independently hydrogen; heavy hydrogen; halogen group; -CN; -SiRR'R"; -NRR'; -P(=O)RR'; Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; Substituted or unsubstituted carbon number Alkynyl group of 2 to 60 carbon atoms; Substituted or unsubstituted alkoxy group of 1 to 60 carbon atoms; Substituted or unsubstituted aryloxy group of 6 to 60 carbon atoms; Substituted or unsubstituted alkylthioxy group of 1 to 60 carbon atoms; Substituted or Unsubstituted arylthioxy group having 6 to 60 carbon atoms; Substituted or unsubstituted alkylsulfoxy group having 1 to 60 carbon atoms; Substituted or unsubstituted arylsulfoxy group having 6 to 60 carbon atoms; Substituted or unsubstituted arylsulfoxy group having 3 to 60 carbon atoms A cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, R, R' and R" are each independently hydrogen; heavy hydrogen; halogen group; -CN; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R12 are each independently hydrogen; heavy hydrogen; halogen group; -CN; -NRR'; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and R and R' are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R12 are each independently hydrogen; heavy hydrogen; halogen group; -CN; -NRR'; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and R and R' are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R12 are each independently hydrogen; heavy hydrogen; halogen group; -CN; -NRR'; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R and R' are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, at least one of R1 to R12 is -NRR'; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, at least one of R1 to R12 is -NRR'; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, at least one of R1 to R12 is -(L)m-(Z)n, and L is a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, and Z is -NRR'; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and R and R' are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, m is an integer of 0 to 5, if 2 or more, L is the same or different, n is an integer of 1 to 5, and if 2 or more, Z is the same or different.

In an exemplary embodiment of the present specification, at least one of R1 to R12 is -(L)m-(Z)n, and L is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and Z is -NRR'; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and R and R' are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, at least one of R1 to R12 is NRR'; or a substituted or unsubstituted heteroaryl group containing 2 to 60 carbon atoms and including N.

In an exemplary embodiment of the present specification, Formula 1 is NRR'; and at least one of a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms and containing N.

In one embodiment of the present specification, L is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.

In one embodiment of the present specification, L is a direct bond; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent fluorenyl group; A substituted or unsubstituted divalent dibenzofuran group; Or it is a substituted or unsubstituted dibenzothiophene group.

는 화학식 1 및 Z와 결합하는 위치이며, 하기 구조는 중수소로 더 치환될 수 있다.In one embodiment of the present specification, L may be a direct bond or may be represented by any of the following structures,

is the position that bonds to Formula 1 and Z, and the structure below may be further substituted with deuterium.

In one embodiment of the present specification, Z is -NRR'; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Z is -NRR'; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Z is -NRR'; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 60 carbon atoms and containing N.

In one embodiment of the present specification, Z is -NRR'; Or it is a substituted or unsubstituted heteroaryl group containing 2 to 30 carbon atoms and containing N.

In one embodiment of the present specification, Z may be -NRR'.

In one embodiment of the present specification, Z is -NRR', and R and R' are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Z is -NRR', and R and R' are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group containing 2 to 30 carbon atoms containing O or S.

In an exemplary embodiment of the present specification, Z is -NRR', and R and R' 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 fluorenyl group; Substituted or unsubstituted dibenzofuran group; Or it may be a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, Z is -NRR', and R and R' are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted by deuterium, a halogen group, -CN, an alkyl group, or a haloalkyl group. energy; Alternatively, it may be a heteroaryl group containing O or S and having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, Z is -NRR', and R and R' are each independently a phenyl group substituted or unsubstituted by deuterium, a halogen group, or an alkyl group; Biphenyl group substituted or unsubstituted by deuterium, halogen group, -CN, alkyl group, or haloalkyl group; Terphenyl group; naphthyl group; A fluorenyl group substituted or unsubstituted with an alkyl group; Dibenzofuran group; Or it may be a dibenzothiophene group.

In one embodiment of the present specification, Z may be a heteroaryl group of 2 to 30 carbon atoms that is substituted or unsubstituted and includes N.

In one embodiment of the present specification, Z may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms including a -C=N- bond.

In this specification, -C=N- bond refers to a double bond of carbon and nitrogen, and examples of heteroaryl groups containing -C=N- bond include pyridine group, pyrimidine group, triazine group, etc. Examples of heteroaryl groups that do not contain -C=N- bonds include carbazole groups.

In one embodiment of the present specification, Z is a substituted or unsubstituted pyrimidine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted quinoxaline group; Substituted or unsubstituted benzoquinazoline group; Substituted or unsubstituted acenaphthopyrimidine group; A substituted or unsubstituted benzothienopyrimidine group; A substituted or unsubstituted benzofuropyrimidine group; Substituted or unsubstituted naphthothienopyrimidine group; Or it may be a substituted or unsubstituted naphthofuropyrimidine group.

In one embodiment of the present specification, Z may be represented by the following formula N-1, N-2, or P.

[Formula N-1]

[Formula N-2]

[Formula P]

In the formulas N-1, N-2 and P,

Any one of X1 to X6 is the position that binds to L,

The remaining groups among X1 to X6 are each independently N or C(R21), and adjacent groups among X1 to

At least two of X1 to X6 are N,

X7 to X10 are each independently N or C(R22),

At least one of X7 to X10 is N,

R21 and R22 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

L31 and L32 are each independently and directly bonded; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted arylene group having 2 to 30 carbon atoms,

R31 and R32 are each independently a halogen group; Cyano group; an alkyl group having 1 to 10 carbon atoms; Haloalkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms,

l31, l32, r31 and r32 are each integers from 1 to 3, and when each is 2 or more, the substituents in parentheses are the same or different from each other,

는 L과 결합하는 위치이다.

is the position where it binds to L.

In an exemplary embodiment of the present specification, when two or more of X1 to X6 are C(R21), R21 is the same as or different from each other.

In an exemplary embodiment of the present specification, when two or more of X7 to X10 are C(R22), R22 is the same as or different from each other.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted benzocarbazole group; Substituted or unsubstituted dibenzocarbazole group; Substituted or unsubstituted azadibenzonaphtoazulene group; Or a substituted or unsubstituted indolocarbazole group.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; Aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium, halogen group, -CN, alkyl group, haloalkyl group, aryl group, or heteroaryl group; Or it is a heteroaryl group having 2 to 30 carbon atoms that is substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with deuterium, a halogen group, -CN, an alkyl group, a haloalkyl group, an aryl group, or a heteroaryl group; Biphenyl group substituted or unsubstituted with deuterium; naphthyl group; triphenylene group; Dibenzofuran group; carbazole group; Benzocarbazole group; Dibenzocarbazole group; Azadibenzonaphtoazulene group; Or it is an indolocarbazole group ringed or unsubstituted with an aryl group.

In an exemplary embodiment of the present specification, substituted or unsubstituted carbazole groups include those bonded to nitrogen or carbon of carbazole.

In one embodiment of the present specification, R22 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

In one embodiment of the present specification, R22 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R22 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R22 is hydrogen; heavy hydrogen; Or it is an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R22 is hydrogen; heavy hydrogen; Or it is a phenyl group.

In an exemplary embodiment of the present specification, L31 and L32 are each independently directly bonded; Or it is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, L31 and L32 are each independently directly bonded; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In an exemplary embodiment of the present specification, L31 and L32 are each independently directly bonded; Or, it is an arylene group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, L31 and L32 are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; Or it is a biphenylene group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R31 and R32 are each independently a halogen group; Cyano group; An alkyl group having 1 to 5 carbon atoms; Haloalkyl group having 1 to 5 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R31 and R32 are each independently a halogen group; Cyano group; methyl group; tert-butyl group; -CF ₃ ; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted fluorenyl group; Dibenzofuran group; Or it is a dibenzothiophene group.

In an exemplary embodiment of the present specification, R31 and R32 are each independently a halogen group; Cyano group; An alkyl group having 1 to 5 carbon atoms; Haloalkyl group having 1 to 5 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or it is a heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R31 and R32 are each independently a halogen group; Cyano group; methyl group; tert-butyl group; -CF ₃ ; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group; Dibenzofuran group; Or it is a dibenzothiophene group.

In one embodiment of the present specification, adjacent groups among X1 to X6 are bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms; Alternatively, it may form a substituted or unsubstituted heterocycle having 2 to 60 carbon atoms.

Specifically, the remainder that is not N among X1 to

In an exemplary embodiment of the present specification, adjacent groups among X1 to X6 are bonded to each other to form a substituted or unsubstituted benzene ring; naphthalene ring; Acenaphthalene ring; benzofuran ring; benzothiophene ring; Naphthofuran ring; Alternatively, it may form a naphthothiophene ring.

는 L과 결합하는 위치이며, 하기 구조식은 중수소; 치환 또는 비치환된 탄소수 1 내지 60의 알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로아릴기로 더 치환될 수 있다.In one embodiment of the present specification, Z may be represented by the following structural formula,

is the position that binds to L, and the structural formula below is deuterium; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Alternatively, it may be further substituted with a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, any one of R1 to R12 is -(L)m-(Z)n, and the remainder of R1 to R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, any one of R1 to R12 is -(L)m-(Z)n, and the remainder of R1 to R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, any one of R1 to R12 is -(L)m-(Z)n, and the remainder of R1 to R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, any one of R1 to R12 is -(L)m-(Z)n, and the remainder of R1 to R12 are each independently hydrogen; heavy hydrogen; tert-butyl group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted dibenzofuran group; Or it may be a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, any one of R1 to R12 is -(L)m-(Z)n, and the remainder of R1 to R12 are each independently hydrogen; heavy hydrogen; an alkyl group having 1 to 10 carbon atoms; Aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium, halogen group, -CN or alkyl group; Or it may be a heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, any one of R1 to R12 is -(L)m-(Z)n, and the remainder of R1 to R12 are each independently hydrogen; heavy hydrogen; tert-butyl group; Phenyl group substituted or unsubstituted by deuterium, halogen group, -CN or alkyl group; Biphenyl group; naphthyl group; Dibenzofuran group; Or it may be a dibenzothiophene group.

In an exemplary embodiment of the present specification, R1 to R6 and R9 to R12 are each independently hydrogen; heavy hydrogen; -NRR'; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R1 to R6 and R9 to R12 are each independently hydrogen; heavy hydrogen; -NRR'; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R7 and R8 are each independently hydrogen; heavy hydrogen; -NRR'; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, R7 and R8 are each independently hydrogen; heavy hydrogen; -NRR'; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R7 and R8 are each independently hydrogen; heavy hydrogen; -NRR'; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In an exemplary embodiment of the present specification, when any one of R1 to R6 and R9 to R12 is -(L)m-(Z)n, R7 and R8 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1 is -(L)m-(Z)n, and R2 to R6 and R9 to R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R2 is -(L)m-(Z)n, and R1, R3 to R6 and R9 to R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R3 is -(L)m-(Z)n, and R1, R2, R4 to R6, R9, R11, and R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R4 is -(L)m-(Z)n, and R1 to R3, R5, R6 and R9 to R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R5 is -(L)m-(Z)n, and R1 to R4, R6 and R9 to R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R6 is -(L)m-(Z)n, and R1 to R5 and R7 to R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R7 is -(L)m-(Z)n, and R1 to R6 and R9 to R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R8 is -(L)m-(Z)n, and R1, R2, R4 to R6 and R9 to R12 are each independently hydrogen; Or it may be deuterium.

In one embodiment of the present specification, R9 is -(L)m-(Z)n, and R1 to R6 and R10 to R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R10 is -(L)m-(Z)n, and R1, R2, R4 to R6, R9, R11, and R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R11 is -(L)m-(Z)n, and R1, R2, R4 to R6, R9, R10, and R12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, R12 is -(L)m-(Z)n, and R1 to R6 and R9 to R11 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, Formula 1 may be represented by the following Formula 1-N or 1-P.

[Formula 1-N]

[Formula 1-P]

In the above formulas 1-N and 1-P,

N1 to N12 and P1 to P12 are each independently hydrogen; heavy hydrogen; halogen group; -CN; -SiRR'R"; -NRR'; -P(=O)RR'; Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; Substituted or unsubstituted carbon number Alkynyl group of 2 to 60 carbon atoms; Substituted or unsubstituted alkoxy group of 1 to 60 carbon atoms; Substituted or unsubstituted aryloxy group of 6 to 60 carbon atoms; Substituted or unsubstituted alkylthioxy group of 1 to 60 carbon atoms; Substituted or Unsubstituted arylthioxy group having 6 to 60 carbon atoms; Substituted or unsubstituted alkylsulfoxy group having 1 to 60 carbon atoms; Substituted or unsubstituted arylsulfoxy group having 6 to 60 carbon atoms; Substituted or unsubstituted arylsulfoxy group having 3 to 60 carbon atoms A cycloalkyl group; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

R, R' and R" are each independently hydrogen; deuterium; halogen group; -CN; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

At least one of N1 to N12 is -(L1)o-(N-Het),

At least one of P1 to P12 is -(L2)p-NRR',

L1 and L2 are each independently and directly bonded; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms,

N-Het is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms containing N,

o and p are each integers from 0 to 5, and when each is 2 or more, the substituents in parentheses are the same or different.

In one embodiment of the present specification, the detailed description of N7 and P7 is the same as the description of R7 described above.

In one embodiment of the present specification, the detailed description of N8 and P8 is the same as the description of R8 described above.

In an exemplary embodiment of the present specification, the detailed description of L1 and L2 is the same as the description of L described above.

In one embodiment of the present specification, N-Het may be a substituted or unsubstituted heteroaryl group containing 2 to 30 carbon atoms and including N.

In one embodiment of the present specification, N-Het may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms including a -C=N- bond.

In one embodiment of the present specification, N-Het is a substituted or unsubstituted pyrimidine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted quinoxaline group; Substituted or unsubstituted benzoquinazoline group; Substituted or unsubstituted acenaphthopyrimidine group; A substituted or unsubstituted benzothienopyrimidine group; A substituted or unsubstituted benzofuropyrimidine group; Substituted or unsubstituted naphthothienopyrimidine group; Or it may be a substituted or unsubstituted naphthofuropyrimidine group.

In an exemplary embodiment of the present specification, N-Het may be represented by the formula N.

In an exemplary embodiment of the present specification, N1, N5, N6, N9, N11, and N12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, P1, P5, P6, P9, P11, and P12 are each independently hydrogen; Or it may be deuterium.

In an exemplary embodiment of the present specification, Formula 1-N may be used as an N-type host.

The formula 1-N has an excellent electron transport ability by having a heterocyclic group containing N.

In one embodiment of the present specification, Formula 1-P may be used as a P-type host.

The formula 1-P necessarily includes an amine group, so hole mobility increases due to the high HOMO level and has an electron blocking effect, which has the effect of lowering the driving voltage when used as a material for the hole transport layer, and has the effect of lowering the driving voltage of the light emitting layer. When used as a material, efficiency is improved through reduction of current leakage and electron confinement effects.

In one embodiment of the present specification, the deuterium content of Formula 1 may be 0% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be greater than 0% and less than or equal to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 5% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0% or 1% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0% or 5% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0% or 10% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0% or 30% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0% or 50% to 100%.

In one embodiment of the present specification, the deuterium content of Chemical Formula 1 may be 0% or 70% to 100%.

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

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

In addition, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved and the uses of the material can be diversified.

In another embodiment of the present specification, a first electrode; It provides an organic light-emitting device comprising a second electrode and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include one or more types of condensed polycyclic compounds of Formula 1. .

In an exemplary embodiment of the present specification, the organic material layer may include one or two types of the condensed polycyclic compound.

In one embodiment of the present specification, the organic layer includes a hole transport layer, and the hole transport layer may include one or more types of condensed polycyclic compounds.

In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may include one or more types of the condensed polycyclic compound.

In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may include one or two types of the condensed polycyclic compound.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include one or more types of the condensed polycyclic compound.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include one or two types of the condensed polycyclic compound.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a condensed polycyclic compound of the formula 1-N as an N-type host, and a condensed polycyclic compound of the formula 1-P as a P-type host. It may contain polycyclic compounds.

When a host is formed by combining two types of condensed polycyclic compounds of Formula 1, that is, a condensed polycyclic compound of Formula 1-N and a condensed polycyclic compound of Formula 1-P, better efficiency and lifespan are achieved than when using a single host. It looks like

Specifically, when the compound of Formula 1-N and the compound of Formula 1-P are used simultaneously as materials for the light emitting layer, an exciplex phenomenon occurs, which has the effect of lowering the driving voltage of the device and improving its lifespan. The exciplex phenomenon is a phenomenon in which energy equivalent to the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released through electron exchange between a molecule with strong donor characteristics and a molecule with strong acceptor characteristics. When a donor (p-host) with a good hole transport ability and an acceptor (n-host) with a good electron transport ability are used as hosts for the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so they are driven. The voltage can be lowered, which can help improve lifespan.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include a condensed polycyclic compound of the formula 1-N as an N-type host.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes a condensed polycyclic compound of the formula 1-N as an N-type host, and a compound of the formula A or B below as a P-type host. may include.

[Formula A]

[Formula B]

In the formulas A and B,

A1 to A5 and B1 to B3 are each independently hydrogen; heavy hydrogen; halogen group; -CN; - A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

Adjacent groups among A2 to A5 may be combined with each other to form a substituted or unsubstituted hydrocarbon ring or heterocycle,

L11 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms,

a1, b1, and b2 are each integers from 1 to 5, and when each is 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, A1 may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, A1 may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, A1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Or it may be a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, A1 may be an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an alkyl group, an aryl group, or a heteroaryl group.

In an exemplary embodiment of the present specification, A2 to A5 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and adjacent groups among A2 to A5 may be bonded to each other to form a substituted or unsubstituted heterocycle.

In an exemplary embodiment of the present specification, A2 to A5 are each independently hydrogen; heavy hydrogen; It may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and adjacent groups among A2 to A5 may be bonded to each other to form a substituted or unsubstituted heteroring.

In an exemplary embodiment of the present specification, at least one of A2 to A5 is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or adjacent groups of A2 to A5 are bonded to each other to form a substituted or unsubstituted heterocycle. can do.

In an exemplary embodiment of the present specification, at least one of A2 to A5 is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, or adjacent groups of A2 to A5 are bonded to each other to form a substituted or unsubstituted indole ring. can do.

In one embodiment of the present specification, at least one of A2 to A5 is a substituted or unsubstituted carbazole group, or adjacent groups of A2 to A5 may be bonded to each other to form a substituted or unsubstituted indole ring.

In an exemplary embodiment of the present specification, the formula A may be represented by the following formula A-1 or A-2.

[Formula A-1]

[Formula A-2]

In the above formulas A-1 and A-2,

A1 is the same as defined in Formula A above,

A11 and A12 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it is a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In one embodiment of the present specification, A11 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present specification, A11 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 quinoline group; Substituted or unsubstituted dibenzofuran group; Or it may be a substituted or unsubstituted dibenzothiophene group.

In one embodiment of the present specification, A12 may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, A12 may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, A12 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Or it may be a substituted or unsubstituted terphenyl group.

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

In an exemplary embodiment of the present specification, B1 to B3 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, B1 and B2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Alternatively, it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

In an exemplary embodiment of the present specification, B1 and B2 may each independently be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In an exemplary embodiment of the present specification, B1 and B2 may each independently be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, B1 and B2 are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Or it may be a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, B3 is hydrogen; heavy hydrogen; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, B3 is hydrogen; heavy hydrogen; Alternatively, it may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, B3 is hydrogen; heavy hydrogen; Or it may be a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, L11 is a direct bond; Alternatively, it may be a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L11 is a direct bond; Or it may be a substituted or unsubstituted phenylene group.

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

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 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 a smaller number of organic material layers.

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

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

The organic light-emitting device according to an embodiment of the present specification uses the above-described condensed polycyclic compound of Formula 1 alone, or uses two types of condensed polycyclic compounds of Formula 1 together to form one or more organic layers. , can be manufactured using conventional organic light emitting device manufacturing methods and materials.

The condensed polycyclic compound of Formula 1 may be formed into an organic 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.

In one embodiment of the present specification, the condensed polycyclic compound of Formula 1 may be used as an N-type host material or a P-type host material depending on the type of substituent.

In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the condensed polycyclic compound of Formula 1 may be used as a material for the blue organic light-emitting device. For example, the condensed polycyclic compound of Formula 1 may be included in the host material of the light-emitting layer of the blue organic light-emitting device.

In another embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the condensed polycyclic compound of Formula 1 may be used as a material for the green organic light-emitting device. For example, the condensed polycyclic compound of Formula 1 may be included in the host material of the emission layer of the green organic light-emitting device.

In another embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the condensed polycyclic compound of Formula 1 may be used as a material for the red organic light-emitting device. For example, the condensed polycyclic compound of Formula 1 may be included in the host material of the emission layer of the red organic light-emitting device.

The organic light emitting device of the present invention may further include one 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 an exciton blocking layer.

1 to 3 illustrate the stacking order of electrodes and organic material layers of an organic light-emitting device according to an exemplary embodiment of the present specification. 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.

Figure 3 illustrates 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 auxiliary layer 303, an electron blocking layer 304, a light emitting layer 305, a hole blocking layer 306, an electron transport layer ( 307) and an electron injection layer 308. 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 the condensed polycyclic compound of Formula 1 may further include other materials as needed.

In the organic light-emitting device according to an exemplary embodiment of the present specification, materials other than the condensed polycyclic compound of Formula 1 are illustrated below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, and are related to the technical field. It can be replaced with known materials.

As the anode material, materials with a relatively large work function can be used, 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); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline 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 multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

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-styrenesulfonate)) etc. 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 specification may be a front-emitting type, a rear-emitting type, or a double-sided emitting type depending on the material used.

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

In addition, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved and the uses of the material can be diversified.

In one embodiment of the present specification, 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 forming the organic layer includes forming one or more organic layers using a composition for an organic layer containing the condensed polycyclic compound of Formula 1. 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.

[Preparation Example 1] Preparation of target compound

1) Preparation of Compound A-1

1,8-dibromonaphthalene 15.0 g (52.45 mmol), (4-chlorophenyl)boronic acid (a) 9.84 g (62.95 mmol), Pd (PPh ₃ ) ₄ (Tetrakis (triphenylphosphine) palladium (0)) 3.03 g (2.62 mmol), and K ₂ CO ₃ 14.5 g (104.91 mmol) were mixed with 1,4-Dioxane. ) was dissolved in 150ml and H ₂ O 30ml and then refluxed at 120°C for 1 hour and 30 minutes. After the reaction was completed, distilled water and dichloromethane (DCM) were added at room temperature for extraction, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:5) to obtain 10.0 g of Compound A-1 (yield 60.06%).

2) Preparation of Compound A

Compound A-1 10.0 g (31.48 mmol), Diphenylacetylene 11.45 g (62.97 mmol), Pd(OAc) ₂ (palladium(II) acetate) 0.71 g (3.15 mmol), Tris (4-chlorophenyl) Phosphine) (Tris(4-chlorophenyl)phosphine) 3.46 g (9.445 mmol) and Ag ₂ CO ₃ 8.68 g (31.49 mmol) were dissolved in 100 mL of 1,2-Dichloroethane and incubated at 80°C. It was refluxed for 18 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:6) to obtain 5 g (38.27%) of Compound A.

3) Preparation of compound 164

Compound A 5 g (12.05 mmol), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (N-([1,1' -biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine) (b) 4.36 g (12.05 mmol), Pd ₂ (dba) ₃ 0.55 g (0.6 mmol), Xphos (2- Dissolve 1.15 g (2.41 mmol) of dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) and 2.32 g (24.1 mmol) of NaOtBu in 50ml of xylene and reflux for 5 hours. did. After the reaction was completed, the produced solid was filtered, washed with methanol (MeOH), and dried. The dried solid was dissolved in chloroform, purified by silica, and the solvent was removed using a rotary evaporator. Recrystallized with acetone to obtain 8 g (89.72%) of target compound 164.

4) Preparation of Compound 101

Compound A 5g (12.05 mmol), (4-(diphenylamino)phenyl)boronic acid ((4-(diphenylamino)phenyl)boronic acid) (b') 3.48g (12.05 mmol), Pd ₂ (dba) ₃ ( 0.55 g (0.6 mmol) of tris(dibenzylideneacetone)dipalladium (0)), 1.15 g (2.41 mmol) _of It was then refluxed for 4 hours. After the reaction was completed, the produced solid was filtered, washed with MeOH, and dried. The dried solid was dissolved in chloroform, purified by silica, and the solvent was removed using a rotary evaporator. Recrystallized with acetone to obtain 6g (79.78%) of target compound 101.

In Preparation Example 1, (4-chlorophenyl)boronic acid (a), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine ( b) and 4-(diphenylamino)phenyl)boronic acid ((4-(diphenylamino)phenyl)boronic acid) (b') instead of intermediate (a) and intermediate (b)/(b') in Table 1 below. The following target compounds were synthesized in the same manner as Preparation Example 1, except that they were used.

compound
number Intermediate (a) Intermediate (b)/(b') target compound transference number 107 50% 108 57% 130 70% 143 65% 162 59% 167 55% 179 66% 195 55% 250 45% 260 59% 263 66% 269 57% 271 62% 279 45% 284 51%

[Preparation Example 2] Preparation of target compound

1) Preparation of Compound B-2

1,8-dibromonaphthalene 15.0 g (52.45 mmol), (4-chlorophenyl)boronic acid (c) 9.84 g (62.95 mmol), Pd(PPh ₃ ) ₄ 3.03 g (2.62 mmol), and K ₂ CO ₃ 14.5 g ( 104.91 mmol) was dissolved in 150ml of 1,4-Dioxane and 30ml of H ₂ O and then refluxed at 120°C for 1 hour and 30 minutes. After the reaction was completed, extraction was performed with distilled water and DCM at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:5) to obtain 10.0 g (60.06%) of compound B-2.

2) Preparation of Compound B-1

Compound A-1 10.0 g (31.48 mmol), Diphenylacetylene 11.45 g (62.97 mmol), Pd(OAc) ₂ 0.71 g (3.15 mmol), Tris(4-chlorophenyl)phosphine 3.46 g (9.445 mmol), and Ag ₂ CO ₃ 8.68 g (31.49 mmol) was dissolved in 100 mL of 1,2-Dichloroethane and refluxed at 80°C for 18 hours. After the reaction was completed, extraction was performed with distilled water and DCM at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:6) to obtain 5 g (38.27%) of compound B-1.

3) Preparation of Compound B

Compound B-1 3.66 g (8.82 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabo Lorane)(4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)) 3.14 g (12.35 mmol), Pd ₂ (dba) ₃ 0.4 g (0.44 mmol), Xphos 0.42 g (0.88 mmol), and KoAc (potassium acetate) 1.73 g (17.64 mmol) were dissolved in 50 ml of 1,4-Dioxane and refluxed for 5 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:6) to obtain 3.82 g (85.51%) of Compound B.

4) Preparation of compound 381

Compound B 3.82 g (7.54 mmol), 2-chloro-4,5-diphenyl-1,3,5-triazine (d) Dissolve 2.02 g (7.54 mmol), 0.35 g (0.38 mmol) of Pd(PPh ₃ ) ₄ , and 2.08 g (15.09 mmol) of K ₂ CO ₃ in 40ml of 1,4-Dioxane and 8ml of H ₂ O and reflux for 3 hours. did. After the reaction was completed, the produced solid was filtered, washed with MeOH, and dried. The dried solid was dissolved in chloroform, purified by silica, and the solvent was removed using a rotary evaporator. Recrystallized with acetone to obtain 3.1 g (67.18%) of target compound 381.

In Preparation Example 2, intermediates (c) and (d) of Table 2 below were used instead of (4-chlorophenyl)boronic acid (c) and 2-chloro-4,5-diphenyl-1,3,5-triazine (d). ) The following target compounds were synthesized in the same manner as Preparation Example 2, except that ) was used.

compound
number intermediate (c) intermediate (d) target compound transference number 386 50% 390 57% 392 70% 414 65% 420 59% 422 55% 425 66% 438 55% 478 45% 489 58% 499 59% 513 66%

[Preparation Example 3] Preparation of target compound

1) Preparation of compound C-2

1,8-dibromonaphthalene 15.0 g (52.45 mmol), phenylboronic acid 7.67 g (62.95 mmol), Pd(PPh ₃ ) ₄ 3.03 g (2.62 mmol), and K ₂ CO ₃ 14.5 g (104.91 mmol) was dissolved in 150ml of 1,4-Dioxane and 30ml of H ₂ O and then refluxed at 120°C for 1 hour and 30 minutes. After the reaction was completed, extraction was performed with distilled water and DCM at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:5) to obtain 11.3 g (76.09%) of compound C-2.

2) Preparation of compound C-1

Compound C-2 11.3 g (39.90 mmol), Diphenylacetylene 14.22 g (79.81 mmol), Pd(OAc) ₂ 0.895 g (3.99 mmol), Tris(4-chlorophenyl)phosphine 4.37 g (11.97 mmol), and Ag ₂ CO ₃ 11 g (39.90 mmol) was dissolved in 100 mL of 1,2-Dichloroethane and refluxed at 80°C for 18 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:6) to obtain 6.5g (42.82%) of compound C-1.

3) Preparation of Compound C

After dissolving 6.5 g (17.08 mmol) of Compound C-1 in 65 ml of chloroform, 0.962 ml (18.78 mmol) of Br ₂ was added dropwise at 0°C. After the reaction was completed, the solid produced at room temperature was filtered, washed with MeOH, and dried. The dried solid was dissolved in chloroform, purified by silica, and the solvent was removed using a rotary evaporator. Recrystallized with acetone to obtain 6.78g (86.48%) of Compound C.

4) Preparation of compound 71

Compound C 5.5 g (12.05 mmol), [1,1'-biphenyl]-4-yl(naphthalen-2-yl)-l2-amine ([1,1'-biphenyl]-4-yl(naphthalen-2 -yl)-l2-amine) (e) 3.55 g (12.05 mmol), Pd ₂ (dba) ₃ 0.55 g (0.6 mmol), Xphos 1.15 g (2.41 mmol), and NaOtBu 2.32 g (24.1 mmol) were added to 50 ml of Xylene After dissolving in , it was refluxed for 5 hours. After the reaction was completed, the produced solid was filtered, washed with MeOH, and dried. The dried solid was dissolved in chloroform, purified by silica, and the solvent was removed using a rotary evaporator. Recrystallized with acetone to obtain 7.2 g (85.71%) of target compound 71.

5) Preparation of Compound 2

Compound C 5.5 g (12.05 mmol), (4-(naphthalen-2-yl(phenyl)amino)phenyl)boronic acid ((4-(naphthalen-2-yl(phenyl)amino)phenyl)boronic acid) (f) 4.08 g (12.05 mmol), 0.55 g (0.6 mmol) of Pd ₂ (dba) ₃ , 1.15 g (2.41 mmol) of Xphos, and 1.45 g (36.15 mmol) of NaOH were dissolved in 50 ml of 1,4-Dioxane and 10 ml of H ₂ O. It was then refluxed for 4 hours. After the reaction was completed, the produced solid was filtered, washed with MeOH, and dried. The dried solid was dissolved in chloroform, purified by silica, and the solvent was removed using a rotary evaporator. Recrystallized with acetone to obtain 7g (86.20%) of target compound 2.

In Preparation Example 3, [1,1'-biphenyl]-4-yl(naphthalen-2-yl)-l2-amine (e), (4-(naphthalen-2-yl(phenyl)amino)phenyl)boron The target compound below was synthesized in the same manner as Preparation Example 3, except that intermediate (e) or (f) of Table 3 below was used instead of acid (f) .

compound
number Intermediates (e)/(f) target compound transference number 2 78% 19 67% 35 72% 43 66% 57 57% 64 69% 68 71% 71 74% 79 61% 96 59%

[Preparation Example 4] Preparation of target compound

1) Preparation of compound D-3

1,8-dibromonaphthalene 15.0 g (52.45 mmol), phenylboronic acid 7.67 g (62.95 mmol), Pd(PPh ₃ ) ₄ 3.03 g (2.62 mmol), and K ₂ CO ₃ 14.5 g (104.91 mmol) were added to 1,4- It was dissolved in 150ml of dioxane and 30ml of H ₂ O and refluxed at 120°C for 1 hour and 30 minutes. After the reaction was completed, extraction was performed with distilled water and DCM at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:5) to obtain 11.3 g (76.09%) of compound D-3.

2) Preparation of compound D-2

Compound D-3 11.3 g (39.90 mmol), Diphenylacetylene 14.22 g (79.81 mmol), Pd(OAc) ₂ 0.895 g (3.99 mmol), Tris(4-chlorophenyl)phosphine 4.37 g (11.97 mmol), and Ag ₂ CO ₃ 11 g (39.90 mmol) was dissolved in 100 mL of 1,2-Dichloroethane and refluxed at 80°C for 18 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:6) to obtain 6.5g (42.82%) of compound D-2.

3) Preparation of Compound D-1

6.5 g (17.08 mmol) of Compound D-2 was dissolved in 65 ml of chloroform, and then 0.962 ml (18.78 mmol) of Br ₂ was added dropwise at 0°C. After the reaction was completed, the solid produced at room temperature was filtered, washed with MeOH, and dried. The dried solid was dissolved in chloroform, purified by silica, and the solvent was removed using a rotary evaporator. Recrystallized with acetone to obtain 6.78g (86.48%) of compound D-1.

4) Preparation of Compound D

Compound D-1 6.78 g (14.76 mmol), Pd(dppf)Cl ₂ ([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)) 0.54 g (0.74 mmol), KoAc 2.89 g ( 29.52 mmol), dissolved in 68ml of 1,4-Dioxane and refluxed at 120°C for 2 hours and 30 minutes. After the reaction was completed, extraction was performed with distilled water and DCM at room temperature, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:3) to obtain 6.2g (80%) of Compound D.

5) Preparation of Compound 310

Compound D 6.2g (12.24 mmol), 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (2-chloro-4,6-di(naphthalen-2-yl) )-1,3,5-triazine) (g) 4.5g (12.24 mmol), Pd(PPh ₃ ) ₄ 0.71g (0.612 mmol), and potassium carbonate 3.4g (24.48 mmol) as 1,4 -Dissolved in 62ml of dioxane and 13ml of H ₂ O and refluxed for 2 hours. After the reaction was completed, the produced solid was filtered, washed with MeOH, and dried. The dried solid was dissolved in chloroform, purified by silica, and the solvent was removed using a rotary evaporator. Recrystallized with acetone to obtain 7.3g (83.81%) of target compound 310.

Except that in Preparation Example 4, intermediate (g) of Table 4 below was used instead of 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine (g). The following target compounds were synthesized in the same manner as Example 4.

compound
number intermediate (g) target compound transference number 309 68% 321 62% 331 70% 337 72% 348 49% 356 52% 357 57%

[Preparation Example 5] Preparation of target compound 378

In Preparation Example 4, instead of 2-chloro-4,6-di(naphthalen-2-yl)-1,3,5-triazine, 2-([1,1'-biphenyl]-4-yl)-4 -(4-chlorophenyl)-6-phenyl-1,3,5-triazine(2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl- Compound 1-378 was synthesized in the same manner as in Preparation Example 4 except that 1,3,5-triazine) was used.

Compound 1-378 (6.545 mmol) was dissolved in 5 ml of D ₆ -benzene, 3.9 ml (44.50 mmol) of Triflic acid was added dropwise, and the mixture was refluxed at 100°C for 2 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried with MgSO ₄ and the solvent was removed using a rotary evaporator. The reaction product was silica purified, and the reaction product was purified by column chromatography (DCM:Hexane=1:4) to obtain 4.9g (93.5%) of compound 378.

The remaining compounds other than those described in Preparation Examples 1 to 5 and Tables 1 to 4 were also prepared in the same manner as described in the above Preparation Examples, and the synthesis results are shown in Tables 5 and 6 below. Table 5 below shows the measured values of ¹ H NMR (CDCl ₃ , 400Mz), and Table 6 below shows the measured values of Field desorption mass spectrometry (FD-MS).

NO ^1H NMR (CDCl ₃ , 300Mz) 2 8.95 (d, 1H), 8.45 (d, 1H), 8.42 (d, 2H), 8.10 (t, 2H), 7.65-7.37 (m, 21H), 7.27 (t, 2H), 7.24 (t, 2H) , 7.11-7.00 (m, 4H) 19 8.95 (d, 1H), 8.48 (d, 1H), 8.42 (d, 2H), 8.25 (d, 2H), 8.10 (t, 2H), 7.74-7.55 (m, 13H), 7.44-7.37 (m, 4H), 7.27-7.24 (m, 6H), 7.08-7.00 (m, 6H) 35 8.95 (d, 1H), 8.48 (d, 1H), 8.42 (d, 2H), 8.10 (dd, 2H), 7.90 (d, 1H), 7.86 (d, 1H), 7.74-7.55 (m, 12H) , 7.44-7.24 (m, 12H), 7.08-7.00 (t, 3H) 43 8.95 (d, 1H), 8.48 (d, 1H), 8.42 (d, 2H), 8.10 (t, 2H), 8.03 (s, 1H), 7.74-7.37 (m, 17H), 7.24 (t, 3H) , 7.08-7.00 (t, 7H) 57 8.95 (d, 1H), 8.48 (d, 1H), 8.42 (d, 2H), 8.10 (t, 2H), 7.74-7.41 (m, 19H), 7.27 (d, 4H), 7.24 (t, 2H) , 7.13-7.00 (m, 5H) 64 8.58 (d, 1H), 8.42 (d, 2H), 8.22 (d, 1H), 8.10 (t, 2H), 7.90-7.75 (m, 5H), 7.58-7.27 (m, 23H), 7.16 (d, 1H) 68 8.58 (d, 1H), 8.42 (d, 2H), 8.22 (d, 1H), 8.10 (t, 2H), 7.98 (d, 1H), 7.81 (t, 1H), 7.75 (d, 2H), 7.65 -7.27 (m, 23H), 6.97 (d, 1H) 71 8.58 (d, 1H), 8.42 (d, 2H), 8.22 (d, 1H), 8.10 (t, 2H), 7.81 (t, 1H), 7.75 (d, 4H), 7.65-7.41 (m, 22H) , 7.27 (d, 4H) 79 8.58 (d, 1H), 8.42 (d, 2H), 8.22 (d, 1H), 8.10 (t, 2H), 7.81 (t, 1H), 7.75 (d, 4H), 7.55-7.41 (m, 20H) , 7.27 (d, 3H), 7.18-7.17 (d, 2H) 96 8.05 (d, 1H), 8.48 (d, 1H), 8.42 (d, 2H), 8.10 (t, 2H), 7.74-7.55 (m, 8H), 7.44-7.37 (m, 4H) 101 8.19 (d, 2H), 7.91 (d, 1H), 7.84 (d, 2H), 7.65-7.41 (m, 15H), 7.27-7.24 (m, 3H), 7.08-7.00 (m, 7H) 107 8.19 (d, 2H), 7.91 (d, 1H), 7.84 (d, 2H), 7.75-7.38 (m, 28H), 7.27 (d, 4H), 7.11 (s, 1H), 7.06 (d, 1H) 108 8.19 (d, 2H), 7.91 (d, 1H), 7.84 (d, 2H), 7.75 (d, 2H), 7.65-7.41 (m, 19H), 7.27-7.17 (m, 7H), 7.08-7.00 ( m, 4H) 130 8.19 (d, 2H), 8.03 (s, 1H), 7.98 (d, 1H), 7.91 (d, 1H), 7.84 (d, 2H), 7.55-7.24 (m, 23H), 7.08 (d, 2H) , 7.00 (t, 1H), 6.91 (d, 1H) 143 8.19 (d, 2H), 8.03 (s, 1H), 7.91 (d, 1H), 7.84 (s, 2H), 7.65-7.41 (m, 17H), 7.24 (t, 4H), 7.08-7.00 (m, 7H), 6.91 (d, 1H) 162 8.19 (d, 2H), 7.90 (d, 1H), 7.84 (d, 2H), 7.65-7.38 (m, 23H), 7.28 (t, 1H), 7.11-7.05 (m, 3H), 6.93 (s, 1H) 164 8.19 (d, 2H), 7.90-7.84 (d, 4H), 7.75-7.27 (m, 26H), 7.16 (d, 1H), 7.08 (d, 1H), 6.93 (s, 1H) 167 8.19 (d, 2H), 8.03 (s, 1H), 7.98 (d, 1H), 7.84 (d, 2H), 7.75-7.27 (m, 26H), 7.08 (d, 1H), 6.93 (s, 1H) , 6.91 (s, 1H) 179 8.19 (d, 2H), 7.84 (d, 2H), 7.75-7.41 (m, 25H), 7.27 (d, 3H), 7.18 (d,1H), 7.17 (d, 1H), 7.08 (d, 1H) , 6.93 (s, 1H) 195 8.19 (d, 2H), 7.91 (d, 1H), 7.84 (d, 2H), 7.75 (d, 2H), 7.65-7.41 (m, 18H), 7.27-7.24 (d, 4H), 7.08-7.00 ( m, 4H) 250 8.19 (d, 2H), 7.91 (d, 1H), 7.84 (d, 2H), 7.65-7.41 (m, 15H), 7.27 (d, 2H), 7.15 (d, 4H), 7.03 (d, 4H) , 2.32 (s, 6H) 260 8.95 (d, 1H), 8.45 (d, 1H), 8.27 (d, 1H), 8.19 (d, 2H), 7.95 (s, 1H), 7.91 (d, 1H), 7.86 (d, 1H), 7.85 (d, 1H), 7.84 (d, 2H), 7.65-24 (m, 22H), 7.08-7.00 (m, 4H) 263 8.19 (d, 2H), 8.03 (s, 1H), 7.91 (d, 1H), 7.84 (d, 2H), 7.65-7.41 (m, 17H), 7.24 (d, 4H), 7.08-7.00 (m, 7H) 269 8.19 (d, 2H), 8.18 (s, 1H), 7.91 (d, 1H), 7.86 (d, 1H), 7.84 (d, 2H), 7.74-7.41 (m, 15H), 7.24 (t, 4H) , 7.16 (d, 1H), 7.08-7.00 (m, 7H), 1.69 (s, 6H) 271 8.19 (d, 2H), 7.91 (d, 1H), 7.86 (d, 1H), 7.84 (d, 2H), 7.78 (d, 1H), 7.65-7.41 (m, 15H), 7.24 (t, 4H) , 7.16 (d, 1H), 7.08-7.00 (m, 7H), 1.69 (s, 6H) 279 8.45 (d, 1H), 8.19 (d, 2H), 7.86 (d, 1H), 7.84 (d, 2H), 7.74-7.41 (m, 17H), 7.31 (t, 1H), 7.24 (t, 2H) , 7.08-7.00 (m, 5H) 284 8.19 (d, 2H), 7.84 (d, 2H), 7.75-7.41 (m, 26H), 7.27 (d, 2H), 7.27 (s, 1H), 7.18 (d, 1H), 7.17 (d, 1H) , 7.08 (d, 1H), 6.93 (s, 1H) 309 8.97 (d, 3H), 8.61 (d, 1H), 8.42 (d, 2H), 8.10 (t, 2H), 8.00 (t, 2H), 7.94 (d, 2H), 7.84-7.81 (m, 6H) , 7.55-7.41 (m, 15H), 310 9.09 (s, 2H), 8.97 (d, 1H), 8.61 (d, 1H), 8.49 (d, 2H), 8.42 (d, 2H), 8.16-8.00 (m, 8H), 7.81 (t, 1H) , 7.67-7.55 (m, 13H), 7.41 (t, 2H) 321 8.97 (d, 1H), 8.61 (d, 1H), 8.55 (d, 1H), 8.42 (d, 2H), 8.36 (d, 2H), 8.10 (t, 2H), 7.82 (d, 1H), 7.81 (d, 1H), 7.67-7.41 (m, 22H), 7.16 (t, 1H), 7.11 (t, 1H) 331 8.97 (d, 1H), 8.61 (d, 1H), 8.50 (d, 1H), 8.42 (d, 2H), 8.30 (d, 2H), 8.13 (d, 2H), 8.10 (t, 2H), 7.89 -7.77 (m, 7H), 7.65-7.55 (m, 10H), 7.41 (t, 3H), 7.35 (t, 1H), 7.25 (d, 2H) 337 8.97 (d, 1H), 8.61 (d, 1H), 8.42 (d, 2H), 8.10 (t, 2H), 7.84-7.81 (m, 4H), 7.70-7.36 (m, 17H), 7.22 (t, 1H) 348 8.97 (d, 1H), 8.61 (d, 1H), 8.55 (d, 2H), 8.42 (d, 2H), 8.13 (d, 1H), 8.10 (t, 2H), 7.84-7.81 (d, 4H) , 7.65-7.41 (m, 20H), 7.16-7.08 (m, 5H) 356 8.95 (d, 1H), 8.48-8.36 (d, 7H), 8.10 (t, 2H), 7.82-7.31 (m, 24H), 357 8.95 (d, 1H), 8.48 (d, 1H), 8.42 (d, 2H), 8.36 (d, 4H), 8.10 (t, 2H), 7.98 (d, 1H), 7.86-7.37 (m, 24H) 378 Not detected by 1H-NMR 381 8.36 (d, 4H), 8.19 (d, 2H), 8.06 (d, 1H), 7.91 (d, 1H), 7.65-7.41 (m, 19H) 386 8.95 (d, 1H), 8.50 (d, 1H), 8.36 (d, 2H), 8.25 (d, 2H), 8.19 (d, 2H), 8.06 (d, 1H), 7.91 (d, 1H), 7.89 (d, 1H), 7.84 (d, 2H), 7.78 (d, 1H), 7.77 (t, 1H), 7.65-7.35 (m, 18H), 7.25 (d, 2H) 390 9.09 (s, 2H), 8.49 (d, 2H), 8.19-8.00 (d, 9H), 7.91 (d, 1H), 7.84 (d, 2H), 7.65-7.41 (m, 17H) 392 8.19 (d, 2H), 8.06 (d, 1H), 8.04 (d, 4H), 7.91 (d, 1H), 7.84 (d, 2H), 7.65-7.31 (m, 17H) 414 8.86 (d, 2H), 8.07 (d, 1H), 8.19 (d, 2H), 8.16 (s, 1H), 7.84-7.41 (m, 26H) 420 8.54 (d, 1H), 8.19 (d, 2H), 7.91 (d, 1H), 7.84 (d, 4H), 7.65-7.41 (m, 19H), 7.29 (d, 1H) 422 8.19 (d, 2H), 8.06 (d, 1H), 7.94 (d, 2H), 7.84 (d, 2H), 7.94 (d, 2H), 7.91 (d, 1H), 7.84 (d, 2H), 7.75 -7.36 (m, 23H), 7.22 (t, 1H) 425 8.55 (d, 1H), 8.28 (d, 1H), 8.19 (d, 2H), 8.13 (d, 1H), 8.11 (d, 1H), 7.84 (d, 4), 7.83 (d, 1H), 7.75 (d, 1H), 7.65-7.41 (m, 19H), 7.16 (t, 1H), 7.11 (t, 1H) 438 8.36 (d, 4H), 8.19 (d, 2H), 7.91 (d, 1H), 7.84 (d, 2H), 7.78 (d, 1H), 7.76 (s, 1H), 7.65-7.41 (m, 22H) , 7.06 (d, 1H) 478 8.36 (d, 2H), 8.19 (d, 2H), 8.06 (d, 1H), 7.98 (d, 1H), 7.91 (d, 1H), 7.84 (d, 2H), 7.83 (s, 1H), 7.65 -7.41 (m, 21H) 499 8.54 (d, 1H), 8.19 (d, 2H), 8.06 (d, 1H), 7.99 (d, 1H), 7.91 (d, 1H), 7.84 (d, 4H), 7.80 (d, 1H), 7.78 (d, 1H), 7.65-7.41 (m, 18H) 513 8.38 (d, 1H), 8.36 (d, 2H), 8.25 (d, 2H), 8.19 (d, 2H), 7.94 (s, 1H), 7.91 (d, 1H), 7.84 (d, 2H), 7.75 -7.41 (m, 23H), 7.25 (d, 2H), 7.06 (d, 1H)

compound FD-MS compound FD-MS 2 m/z=693.28 (C ₅₂ H ₃₅ N=673.86) 19 m/z=699.29 (C ₅₄ H ₃₇ N=699.90) 35 m/z=739.32 (C ₅₇ H ₄₁ N=739.96) 43 m/z=713.27 (C ₅₄ H ₃₅ NO=713.88) 57 m/z=717.28 (C ₅₄ H ₃₆ FN=717.89) 64 m/z=739.32 (C ₅₇ H ₄₁ N=739.96) 68 m/z=713.27 (C ₅₄ H ₃₅ NO=713.88) 71 m/z=699.29 (C ₅₄ H ₃₇ N=699.90) 79 m/z=699.29 (C ₅₄ H ₃₇ N=699.90) 96 m/z=717.41 (C ₅₄ H ₁₉ D ₁₈ N=718.01) 101 m/z=623.26 (C ₄₈ H ₃₃ N=623.80) 107 m/z=749.31 (C ₅₈ H ₃₉ N=749.96) 108 m/z=699.29 (C ₅₄ H ₃₇ N=699.90) 130 m/z=713.27 (C ₅₄ H ₃₅ NO=713.88) 143 m/z=713.27 (C ₅₄ H ₃₅ NO=713.88) 162 m/z=713.31 (C ₅₅ H ₃₉ N=713.92) 164 m/z=739.32 (C ₅₇ H ₄₁ N=739.96) 167 m/z=713.27 (C ₅₄ H ₃₅ NO=713.88) 179 m/z=699.29 (C ₅₄ H ₃₇ N=699.90) 195 m/z=703.32 (C ₅₄ H ₃₃ D ₄ N=703.92) 250 m/z=651.29 (C ₅₀ H ₃₇ N=651.85) 260 m/z=779.26 (C ₅₈ H ₃₇ NS=780.00) 263 m/z=713.27 (C ₅₄ H ₃₅ NO=713.88) 269 m/z=739.32 (C ₅₇ H ₄₁ N=739.96) 271 m/z=739.32 (C ₅₇ H ₄₁ N=739.96) 279 m/z=653.22 (C ₄₈ H ₃₁ NS=653.84) 284 m/z=699.29 (C ₅₄ H ₃₇ N=699.90) 309 m/z= 711.27 (C ₅₃ H ₃₃ N ₃ =711.87) 310 m/z= 711.27 (C ₅₃ H ₃₃ N ₃ =711.87) 321 m/z= 776.29 (C ₅₇ H ₃₆ N ₄ =776.94) 331 m/z=710.27 (C ₅₄ H ₃₄ N ₂ =710.88) 337 m/z=624.22 (C ₄₆ H ₂₈ N ₂ O=624.74) 348 m/z=838.31 (C ₆₂ H ₃₈ N ₄ =839.01) 356 m/z=777.28 (C ₅₇ H ₃₅ N ₃ O=777.93) 357 m/z=777.28 (C ₅₇ H ₃₅ N ₃ O=777.93) 378 m/z=800.53 (C ₅₇ D ₃₇ N ₃ =801.17) 381 m/z=611.24 (C ₄₅ H ₂₉ N ₃ =611.75) 386 m/z= 737.28 (C ₅₅ H ₃₅ N ₃ =737.91) 390 m/z= 711.27 (C ₅₃ H ₃₃ N ₃ =711.87) 392 m/z=647.22 (C ₄₅ H ₂₇ F ₂ N ₃ =647.73) 414 m/z=660.26 (C ₅₀ H ₃₂ N ₂ =660.82) 420 m/z=674.24 (C ₅₀ H ₃₀ N ₂ O=674.80) 422 m/z=700.25 (C ₅₂ H ₃₂ N ₂ O=700.84) 425 m/z=723.27 (C ₅₄ H ₃₃ N ₃ =723.88) 438 m/z=777.28 (C ₅₇ H ₃₅ N ₃ O=777.93) 478 m/z=701.25 (C ₅₁ H ₃₁ N ₃ O=701.83) 499 m/z=690.21 (C ₅₀ H ₃₀ N ₂ S=690.86) 513 m/z= 763.30 (C ₅₇ H ₃₇ N ₃ =763.94)

<Experimental Example 1>

(1) Manufacturing of organic light emitting devices (Red Single Host & Mix Host)

- Comparative Examples 1 to 9 and Examples 1 to 37

A glass substrate coated with a thin film of ITO/Ag/ITO with a thickness of 115Å/100Å/15Å was washed ultrasonically with distilled water. After washing with distilled water, it was ultrasonic washed with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UV for 5 minutes using UV in a UV cleaner. Afterwards, the substrate was transferred to a plasma cleaner (PT), then plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic deposition. On the ITO electrode (anode), a common layer of hole injection layer (HAT-CN) 100Å, hole transport layer (α-NPB) 1100Å, light auxiliary layer (TPD(N-([1,1'-biphenyl]-4-yl )-N,1'-diphenyl-1'H-spiro[fluorene-9,5'-naphtho[8,1,2,3-cdef]carbazol]-7'-amine)) 800Å and electron blocking layer (TAPC) (N-([1,1'-biphenyl]-4-yl)-N,1'-diphenyl-1'H-spiro[fluorene-9,5'-naphtho[8,1,2,3-cdef] carbazol]-7'-amine)) 150Å was formed. A light emitting layer was thermally vacuum deposited thereon as follows.

The light emitting layer was deposited from a single source as a red host, a single compound listed in Table 7 below, or two types of compounds listed in Table 8 below, and (piq) ₂ (Ir)(acac) was used as a red phosphorescent dopant to the host ( piq) ₂ (Ir)(acac) was doped with 3 wt% and deposited to 400 Å. Afterwards, 30Å of Bphen was deposited as a hole blocking layer, and 250Å of TPBI was deposited on top of it as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10Å on the electron transport layer to form an electron injection layer, and then a silver (Ag) cathode was deposited to a thickness of 200Å to form the cathode on the electron injection layer, thereby reducing the organic electric field. A light emitting device was manufactured. Meanwhile, all organic compounds required for OLED device production were purified by vacuum sublimation under 10 ^-8 to 10 ^-6 torr for each material and used for OLED production.

At this time, comparative compounds A to G used in Comparative Examples 1 to 9 are as follows.

(2) Driving voltage and luminous efficiency of organic electroluminescent devices

The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using McScience's M7000, and the standard luminance was measured to be 6,000 cd using the lifespan measurement equipment (M6000) manufactured by McScience using the measurement results. When /m ² , T95 was measured. Above, T95 refers to the lifespan (unit: h, time), which is the time at which the initial luminance reaches 95%.

Table 7 below is an example of applying a single host material, and Table 8 shows the use of a compound with good hole transport ability (donor (p-Host)) or a compound of Formula A or B among the condensed polycyclic compounds of the present invention as the first host. This is an example of depositing two host compounds from one source, using a compound (acceptor (n-Host)) with good electron transport ability among the condensed polycyclic compounds of the present invention as the second host.

compound driving voltage
(V) efficiency
(cd/A) Color coordinates
(x, y) life span
(T95) Comparative Example 1 A 4.80 4.5 (0.682, 0.317) 28 Comparative Example 2 B 4.78 5.2 (0.691, 0.309) 30 Comparative Example 3 C 4.87 5.1 (0.675, 0.325) 20 Comparative Example 4 D 4.47 8.6 (0.681, 0.319) 40 Comparative Example 5 E 4.39 7.1 (0.675, 0.325) 46 Comparative Example 6 F 4.42 9.9 (0.684, 0.316) 42 Comparative Example 7 G 4.38 7.3 (0.674, 0.326) 44 Example 1 2 4.31 10.4 (0.682, 0.317) 56 Example 2 35 4.28 12.6 (0.675, 0.325) 62 Example 3 43 4.25 13.2 (0.682, 0.317) 65 Example 4 57 4.22 13.4 (0.691, 0.309) 68 Example 5 68 4.18 13.8 (0.691, 0.309) 72 Example 6 96 4.29 10.8 (0.675, 0.325) 80 Example 7 108 4.33 11.9 (0.681, 0.319) 58 Example 8 130 4.22 12.8 (0.682, 0.317) 64 Example 9 143 4.39 9.7 (0.675, 0.325) 52 Example 10 162 4.31 11.4 (0.669, 0.321) 60 Example 11 179 4.26 12.4 (0.681, 0.319) 61 Example 12 271 4.42 8.5 (0.691, 0.309) 48 Example 13 279 4.32 11.5 (0.681, 0.319) 61 Example 14 284 4.35 11.2 (0.678, 0.322) 59

first host
(P) second host
(N) weight
ratio
(P:N) driving voltage
(V) efficiency
(cd/A) Color coordinates
(x, y) life span
(T ₉₅ ) Comparative Example 8 D A 1:1 4.42 12.6 (0.669, 0.321) 55 Example 15 E 357 1:1 4.17 19.8 (0.691, 0.309) 85 Example 16 F 386 1:1 4.26 18.2 (0.681, 0.319) 75 Example 17 2 A 1:2 4.18 18.6 (0.678, 0.322) 77 Example 18 43 B 1:2 4.24 19.4 (0.685, 0.315) 82 Comparative Example 9 F C 1:2 4.48 11.5 (0.668, 0.351) 50 Example 19 64 390 1:3 3.76 30.0 (0.681, 0.319) 199 Example 20 68 392 1:3 3.70 31.5 (0.683, 0.317) 208 Example 21 68 414 1:3 3.81 28.7 (0.675, 0.325) 195 Example 22 68 420 1:3 3.66 32.5 (0.684, 0.316) 227 Example 23 179 425 1:2 3.68 32.2 (0.682, 0.317) 224 Example 24 271 309 1:2 3.82 27.8 (0.675, 0.325) 185 Example 25 279 309 1:2 3.80 28.6 (0.682, 0.317) 196 Example 26 19 438 1:1 3.71 31.1 (0.691, 0.309) 214 Example 27 35 438 1:1 3.69 32.2 (0.681, 0.319) 220 Example 28 57 478 1:1 3.83 27.1 (0.682, 0.317) 180 Example 29 71 478 1:1 3.85 26.6 (0.691, 0.309) 174 Example 30 130 337 1:1 3.80 28.8 (0.684, 0.316) 196 Example 31 130 489 1:2 3.85 26.4 (0.683, 0.317) 176 Example 32 130 513 1:3 3.88 26.0 (0.669, 0.321) 170 Example 33 A-1 420 1:2 3.68 32.8 (0.681, 0.319) 226 Example 34 A-2 425 1:1 3.70 32.2 (0.675, 0.325) 224 Example 35 A-15 438 1:3 3.66 33.0 (0.682, 0.317) 230 Example 36 B-1 392 1:2 3.67 32.4 (0.684, 0.316) 225 Example 37 B-6 438 1:1 3.74 31.5 (0.691, 0,309) 216

From Table 7, it can be seen that the organic light-emitting device containing the condensed polycyclic compound of the present invention has a lower driving voltage, higher luminous efficiency, and longer lifespan than the organic light-emitting device using comparative compounds A to G.

Table 8 above shows a case where two types of hosts are combined and included in the organic material layer of an organic light-emitting device, specifically, two types of condensed polycyclic compounds of the present invention are used, or one of the condensed polycyclic compounds of the present invention with good electron transport ability is used. Compounds and compounds of formula A or B were used. Comparing the results in Table 7 and Table 8 above, it can be seen that the driving voltage, efficiency, and lifespan can be improved when two types of hosts are combined. This result can be expected to indicate that an exciplex phenomenon occurs due to the simultaneous inclusion of two compounds. The exciplex phenomenon is a phenomenon in which energy equivalent to the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is emitted through electron exchange between a molecule with strong donor characteristics and a molecule with strong acceptor characteristics. am. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts for the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so the driving voltage can be lowered, thereby helping to improve lifespan. When the exciplex phenomenon occurs, a new S1 (singlet state) energy level and T1 (triplet state) energy level are formed, and changes in PL that are red shifted from each molecule can be confirmed.

When an exciplex phenomenon occurs between two molecules, Reverse Intersysterm Crossing (RISC) occurs, and internal quantum efficiency can increase to 100%.

In particular, in the case of the compound of the formula 1-P, a red-shifted PL change is observed upon injection of the acceptor (n-host), a compound of the formula 1-N, which has a good electron transport ability, forming an ecxiplex. This can help improve luminous properties. In addition, it was confirmed that the lifespan was significantly improved due to appropriate movement of the light-emitting zone in the light-emitting layer as the acceptor (n-Host), a compound corresponding to the formula 1-N with good electron transport ability, was injected.

The HOMO, LUMO, bandgap, and T1 values of comparative compounds A to G and the compounds of the present invention used in some examples are listed in Table 9 below.

compound HOMO
(eV) LUMO
(eV) Band Gap T1
(eV) Comparative Compound A -5.46 -2.33 3.14 2.22 Comparative compound B -5.77 -2.30 3.48 2.18 Comparative Compound C -5.65 -2.47 3.19 2.09 Comparative Compound D -5.16 -1.75 3.41 2.25 Comparative compound E -5.29 -2.02 3.27 2.21 Comparative Compound F -5.22 -1.84 3.38 2.19 Comparative compound G -5.18 -1.76 3.42 2.20 Compound 35 -5.14 -1.72 3.42 2.12 Compound 167 -5.30 -1.77 3.53 2.13 Compound 357 -5.41 -2.29 3.12 2.11 Compound 390 -5.46 -2.24 3.22 2.09

When the T1 level is low, like the compound of the present invention, the gap with the dopant is small and energy transfer from the host to the dopant is easy, resulting in high efficiency. In addition, the planar core can have fast mobility due to good π-π stacking in the deposition layer, and has a high Tg value, so it has very good structural stability.

When an amine group, which is a donor with good hole transport ability, is used as a substituent, the hole mobility increases due to the high HOMO level and has an electron blocking effect, which has the effect of lowering the driving voltage when used as a material for the hole transport layer. When used as a material for a light emitting layer, efficiency is improved through reduction of current leakage and electron confinement effects. If you mix a P-type host among the compounds of the present invention with an N-type host with a strong acceptor tendency among the compounds of the present invention, the lifespan can be increased due to the exciplex phenomenon.

100: substrate
200: anode
300: Organic layer
301: hole injection layer
302: hole transport layer
303: Light auxiliary layer
304: Electronic blocking layer
305: light emitting layer
306: hole blocking layer
307: electron transport layer
308: electron injection layer
400: cathode

Claims (13)

Condensed polycyclic compound of formula 1:
[Formula 1]

In Formula 1,
R1 to R12 are each independently hydrogen; heavy hydrogen; -NRR'; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
At least one of R1 to R12 is -(L)m-(Z)n,
L is a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,
Z is -NRR'; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
R and R' are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
m is an integer from 0 to 5, and if 2 or more, L is the same or different,
n is an integer from 1 to 5, and if 2 or more, Z is the same or different,
‘Substituted or unsubstituted’ means deuterium; halogen group; -CN; C1 to C30 alkyl group; C1 to C30 haloalkyl group; Aryl group of C6 to C30; and C2 to C30 heteroaryl groups, or substituted or unsubstituted with one or more substituents connected to two or more substituents. delete The method according to claim 1, wherein any one of R1 to R12 is -(L)m-(Z)n, and the remainder of R1 to R12 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a condensed polycyclic compound that is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms. The method of claim 1, wherein Z is -NRR'; Or a condensed polycyclic compound that is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms and containing N. The method according to claim 1, wherein the formula 1 is a condensed polycyclic compound represented by the following formula 1-N or 1-P:
[Formula 1-N]

[Formula 1-P]

In the formulas 1-N and 1-P,
N1 to N12 and P1 to P12 are each independently hydrogen; heavy hydrogen; -NRR'; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
At least one of N1 to N12 is -(L1)o-(N-Het),
At least one of P1 to P12 is -(L2)p-NRR',
R and R' are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,
L1 and L2 are each independently and directly bonded; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,
N-Het is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms containing N,
o and p are each integers from 0 to 5, and when each is 2 or more, the substituents in parentheses are the same or different. The condensed polycyclic compound according to claim 1, wherein the deuterium content of Formula 1 is 0% or 5% to 100%, and the deuterium content is a ratio of the number of deuterium to the total number of hydrogen and deuterium in Formula 1. The condensed polycyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

first electrode; An organic light-emitting device comprising a second electrode and one or more organic material layers provided between the first electrode and the second electrode,
An organic light-emitting device wherein at least one of the organic layers includes at least one condensed polycyclic compound according to any one of claims 1 and 3 to 7. The organic light-emitting device of claim 8, wherein the organic material layer includes one or two types of the condensed polycyclic compound. The organic light-emitting device of claim 8, wherein the organic material layer includes a hole transport layer, and the hole transport layer includes one or more types of the condensed polycyclic compound. The organic light-emitting device of claim 8, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes one or more types of the condensed polycyclic compound. The organic light-emitting device of claim 8, wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes one or more types of the condensed polycyclic compound. The organic light emitting device of claim 8, wherein the organic light emitting device further includes one 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. device.

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