KR20220063428A - Heterocyclic compound, organic light emitting device comprising same and and composition for organic layer of organic light emitting device - Google Patents

Abstract

The present application provides a heterocyclic compound, an organic light emitting device in which the heterocyclic compound is contained in an organic material layer, and a composition for the organic material layer. The heterocyclic compound represented by chemical formula 1 can be used as a material of a light emitting layer of the organic light emitting device. In addition, when the heterocyclic compound represented by the chemical formula 1 is used in the organic light emitting device, it is possible to lower driving voltage, and improve light efficiency of a device, and thus improve lifespan characteristics of the device due to the thermal stability of the compound.

Description

Heterocyclic compound, organic light emitting device comprising same, and composition for organic material layer of organic light emitting device {HETEROCYCLIC COMPOUND, ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME AND AND COMPOSITION FOR ORGANIC LAYER OF ORGANIC LIGHT EMITTING DEVICE}

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

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

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair, and then disappear and emit light. The organic thin film may be composed of a single layer or multiple layers, if necessary.

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of forming the light emitting layer by itself may be used, or a compound capable of serving as a host or dopant of the host-dopant light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may be used.

In order to improve the performance, lifespan, or efficiency of an organic light emitting diode, the development of a material for an organic thin film is continuously required.

U.S. Patent No. 4,356,429

An object of the present invention is to provide a heterocyclic compound, an organic light emitting device including the same, and a composition for an organic material layer of an organic light emitting device.

An exemplary embodiment of the present application provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a is an integer from 0 to 2, and when a is 2, L1 in parentheses are the same as or different from each other,

Ar1 is a substituted or unsubstituted C6-C60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

결합을 1개 이상 포함하는 탄소수 2 내지 60의 단환 또는 다환의 헤테로고리기이고,N-Het is substituted or unsubstituted,

It is a monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more bonds,

R1 and Rp are hydrogen; heavy hydrogen; cyano group; Or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, p is an integer of 0 to 3, and when p is 2 or more, Rp in parentheses is the same as or different from each other.

In addition, another exemplary embodiment of the present application is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is described above. There is provided an organic light emitting device comprising a heterocyclic compound represented by Formula 1.

Another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device including the heterocyclic compound represented by Formula 1 above.

The heterocyclic compound according to an exemplary embodiment of the present application may be used as an organic material layer material of an organic light emitting device. The heterocyclic compound may be used as a material for a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. in an organic light emitting device. In particular, the heterocyclic compound represented by Formula 1 may be used as a material of the light emitting layer of the organic light emitting device. In addition, when the heterocyclic compound represented by Formula 1 is used in an organic light emitting device, it is possible to lower the driving voltage of the device, improve the light efficiency, and improve the lifespan characteristics of the device by the thermal stability of the compound.

1 to 3 are views schematically showing a stacked structure of an organic light emitting device according to an exemplary embodiment of the present application, respectively.

Hereinafter, the present application will be described in detail.

An exemplary embodiment of the present application provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a is an integer from 0 to 2, and when a is 2, L1 in parentheses are the same as or different from each other,

Ar1 is a substituted or unsubstituted C6-C60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

결합을 1개 이상 포함하는 탄소수 2 내지 60의 단환 또는 다환의 헤테로고리기이고,N-Het is substituted or unsubstituted,

It is a monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more bonds,

R1 and Rp are hydrogen; heavy hydrogen; cyano group; Or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, p is an integer of 0 to 3, and when p is 2 or more, Rp in parentheses is the same as or different from each other.

결합을 1개 이상 포함하는 단환 또는 다환의 헤테로고리기를 가짐으로써, 전자가 더 풍부해지고 열에 안정해지고, 디벤죠퓨란 코어 중 Ar1이 치환된 벤젠고리 쪽에 N,N을 가짐으로써, LUMO영역이 확장되어 정공과 전자의 균형 또한 알맞게 된다. 이에 따라 상기 화학식 1로 표시되는 화합물을 소자에 사용할 경우 소자의 구동전압을 낮추고, 광 효율을 향상시키며, 화합물의 열적 안정성에 의하여 소자의 수명 특성을 향상시킬 수 있다.In Formula 1, Ar1 is an aryl group or a heteroaryl group, N-Het is

By having a monocyclic or polycyclic heterocyclic group containing one or more bonds, electrons are more abundant and stable to heat. The balance of holes and electrons is also appropriate. Accordingly, when the compound represented by Formula 1 is used in a device, it is possible to lower the driving voltage of the device, improve light efficiency, and improve the lifespan characteristics of the device by thermal stability of the compound.

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

In the present specification, "substituted or unsubstituted" refers to a straight-chain or branched alkyl having 1 to 60 carbon atoms; straight-chain or branched alkenyl having 2 to 60 carbon atoms; linear or branched alkynyl having 2 to 60 carbon atoms; monocyclic or polycyclic cycloalkyl having 3 to 60 carbon atoms; monocyclic or polycyclic heterocycloalkyl having 2 to 60 carbon atoms; monocyclic or polycyclic aryl having 6 to 60 carbon atoms; monocyclic or polycyclic heteroaryl having 2 to 60 carbon atoms; -SiRR'R"; -P(=O)RR'; alkylamine having 1 to 20 carbon atoms; monocyclic or polycyclic arylamine having 6 to 60 carbon atoms; and monocyclic or polycyclic heteroarylamine having 2 to 60 carbon atoms It means that it is substituted or unsubstituted with one or more substituents selected from the group, or substituted or unsubstituted with a substituent to which two or more substituents selected from the exemplified substituents are connected, wherein R, R' and R" are the same as or different from each other, each independently hydrogen; heavy hydrogen; halogen; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C 6 to C 60 aryl; Or it means that it is a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms.

In the present 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 ( ² H, Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In the 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 may come as a substituent are hydrogen or deuterium. That is, in the case of deuterium, deuterium is an isotope of hydrogen, and some hydrogen atoms may be isotope deuterium, and the content of deuterium may be 0% to 100%.

In an exemplary embodiment of the present application, in "when a substituent is not indicated in the chemical formula or compound structure", the content of deuterium is 0%, the content of hydrogen is 100%, and all of the substituents explicitly exclude deuterium such as hydrogen If not, hydrogen and deuterium may be mixed and used in the compound.

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

In an exemplary embodiment of the present application, isotopes have the same atomic number (Z), but isotopes that have different mass numbers (A) have the same number of protons, but neutrons It can also be interpreted as an element with a different number of (neutron).

In the exemplary embodiment of the present application, the meaning of the content of specific substituents T% is T2 when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents 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 함량 20%라는 것은 하기 구조식으로 표시될 수 있다.That is, in one example,

20% of the content of deuterium 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 among them, if the number of deuterium is 1 (T2 in the formula), it will be expressed as 20% can That is, the 20% content of deuterium in the phenyl group may be represented by the following structural formula.

In addition, in the exemplary embodiment of the present application, in the case of "a phenyl group having a deuterium content of 0%", it may mean a phenyl group that does not contain a deuterium atom, that is, has 5 hydrogen atoms.

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

In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, 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, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl 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-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20. Specific examples include a 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 are not limited thereto.

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

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. may be It is not limited.

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 other substituents. Here, polycyclic means a group in which a cycloalkyl group is directly connected to another ring group or condensed. Here, the other ring group may be a cycloalkyl group, but may be a different type of ring group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like. The carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, 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, and the like, but is not limited thereto.

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

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 other substituents. Here, polycyclic means a group in which an aryl group is directly connected or condensed with another ring group. Here, the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like. The aryl group includes a spiro group. The carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrethyl group Nyl group, tetracenyl group, pentacenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof and the like, but is not limited thereto.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, and is represented by -SiR101R102R103, R101 to R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. It is not limited.

In the present specification, the phosphine oxide group is represented by -P(=O)R104R105, R104 and R105 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; an alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; And it may be a substituent consisting of at least one of a heterocyclic group. The phosphine oxide group specifically includes, but is not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide, and the like.

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

In the present specification, the spiro group is a group including a spiro structure, and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorenyl group. Specifically, the spiro group may include any one of the groups of the following structural formula.

In the present specification, the heteroaryl group includes S, O, Se, N or Si as a hetero atom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which a heteroaryl group is directly connected or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may be a different type of ring group, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a 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, quinazolylyl group, naphthyridyl group, acridinyl group, phenanthridyl group Nyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene 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, phenothiazinyl group, phthalazinyl group, naphthylidinyl group, phenanthrolinyl group, Benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl group , pyrido [1,2-b] indazolyl group, pyrido [1,2-a] imidazo [1,2-e] indolinyl group, 5,11-dihydroindeno [1,2-b ] a carbazolyl group, and the like, but is not limited thereto.

In the present specification, the amine group is a monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH ₂ ; dialkylamine group; diarylamine group; diheteroarylamine group; an alkylarylamine group; an alkyl heteroarylamine group; And it may be selected from the group consisting of an aryl heteroarylamine group, the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorene There is a nylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but is not limited thereto.

In the present specification, the arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied. In addition, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the heteroaryl group described above may be applied.

As used herein, the "adjacent" group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. can For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups.

The heterocyclic compound according to an exemplary embodiment of the present application is characterized in that it is represented by Formula 1 above. More specifically, the heterocyclic compound represented by Chemical Formula 1 may be used as an organic material layer material of an organic light emitting device due to the structural characteristics of the core structure and substituents as described above.

In an exemplary embodiment of the present application, L1 of Formula 1 is a direct bond; Or it may be a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In an exemplary embodiment of the present application, L1 is a direct bond; Or it may be a substituted or unsubstituted arylene group having 6 to 40 carbon atoms.

In an exemplary embodiment of the present application, L1 is a direct bond; Or it may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In another exemplary embodiment, L1 is a direct bond; or a phenylene group.

In another exemplary embodiment, L1 is a direct bond.

In another exemplary embodiment, L1 is a phenylene group.

In the exemplary embodiment of the present application, in Formula 1, a is an integer of 0 to 2, and when a is 2, L1 may be the same as or different from each other.

In another exemplary embodiment, a is 0.

In another exemplary embodiment, a is 1.

In another exemplary embodiment, a is 2.

In the exemplary embodiment of the present application, when a is 2 or more, L1 in parentheses may be the same as or different from each other.

In an exemplary embodiment of the present application, Ar1 of Formula 1 is a substituted or unsubstituted 6 to 60 aryl group; Or it may be a substituted or unsubstituted 2 to 60 heteroaryl group.

In an exemplary embodiment of the present application, Ar1 is a substituted or unsubstituted 6 to 40 aryl group; Or it may be a substituted or unsubstituted 2 to 40 heteroaryl group.

In an exemplary embodiment of the present application, Ar1 is a substituted or unsubstituted 6 to 20 aryl group; Or it may be a substituted or unsubstituted 2 to 20 heteroaryl group.

In an exemplary embodiment of the present application, Ar1 is a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; Or it may be a substituted or unsubstituted carbazole group.

결합을 1개 이상 포함하는 단환 또는 다환의 헤테로고리기일 수 있다.In an exemplary embodiment of the present application, N-Het of Formula 1 is substituted or unsubstituted,

It may be a monocyclic or polycyclic heterocyclic group including one or more bonds.

In an exemplary embodiment of the present application, N-Het may be a group represented by the following Chemical Formula A.

[Formula A]

In the formula A,

X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, X5 is CR15 or N, wherein X1 to X5 at least one of them is N;

은 상기 화학식 1과 연결되는 부위이다.R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C 3 to C 60 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; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiR101R102R103; -P(=O)R104R105; and -NR106R107, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or a hetero ring, wherein R101 to R107 are the same as or different from each other, and each independently Hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

is a site connected to Formula 1 above.

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

[Formula A-1]

[Formula A-2]

의 정의는 화학식 A 와 같다.In Formulas A-1 and A-2, X1, X3, X5, R12, R14 and

The definition is the same as in Formula A.

In an exemplary embodiment of the present application, Chemical Formula A may be represented by any one of the following Group A.

[Group A]

의 정의는 화학식 A와 같다.R11 to R15 of group A and

The definition is the same as in Formula A.

In another exemplary embodiment, R1 and Rp of Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; Or it may be a substituted or unsubstituted C1-C60 alkyl group.

In another exemplary embodiment, R1 and Rp are the same as or different from each other, and each independently hydrogen; or deuterium.

In another embodiment, R1 and Rp are both hydrogen.

In another embodiment, both R1 and Rp are deuterium.

In the exemplary embodiment of the present application, p in Formula 1 is an integer of 0 to 3, and when p is 2 or more, Rp may be the same as or different from each other.

In another exemplary embodiment, p is 0.

In another exemplary embodiment, p is 1.

In another exemplary embodiment, p is 2.

In another exemplary embodiment, p is 3.

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, the definitions of L1, Ar1, R1, N-Het and a are the same as in Formula 1,

R2 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; or a substituted or unsubstituted C 1 to C 60 alkyl group.

In another exemplary embodiment, R2 to R5 are the same as or different from each other, and each independently hydrogen; or deuterium.

In another exemplary embodiment, R2 to R5 are all hydrogen.

In another exemplary embodiment, R2 to R5 are all deuterium.

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

[Formula 1-1-1]

[Formula 1-2-1]

[Formula 1-3-1]

[Formula 1-4-1]

상기 화학식 1-1-1 내지 1-4-1에 있어서, L1, R1, Rp, N-Het, a 및 p의 정의는 화학식 1과 동일하고,

In Formulas 1-1-1 to 1-4-1, the definitions of L1, R1, Rp, N-Het, a and p are the same as in Formula 1,

Y1 and Y2 are each independently O; S; CRaRb or NRc, wherein Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 60 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, wherein Rc is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

R16 to R23 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; or a substituted or unsubstituted C 1 to C 60 alkyl group; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, b is an integer from 0 to 3, c to h are each independently an integer from 0 to 4, i is an integer from 0 to 6, b to i When each is 2 or more, the substituents in parentheses are the same as or different from each other.

In an exemplary embodiment of the present application, Rc may be a substituted or unsubstituted C6-C40 aryl group.

In the exemplary embodiment of the present application, Rc may be a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present application, Rc is a substituted or unsubstituted phenyl group.

은 하기 그룹 B 중 어느 하나로 표시되는 것일 수 있다.In an exemplary embodiment of the present application, the formula 1-3-1

may be represented by any one of the following group Bs.

[Group B]

는 L1과 결합하는 위치를 의미한다. Y2, R20, R21, g and f of group B have the same definitions as in Formula 1-3-1,

means a position that binds to L1.

은 하기 그룹 C 중 어느 하나로 표시되는 것일 수 있다.In an exemplary embodiment of the present application, the formula 1-4-1

may be represented by any one of the following group C.

[Group C]

는 L1과 결합하는 위치를 의미한다. The definitions of R22, R23, h and i of Group C are the same as in Formula 1-4-1,

means a position that binds to L1.

According to an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

In addition, by introducing various substituents into the structure of Formula 1, compounds having intrinsic properties of the introduced substituents can be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, an electron transport layer material, and a charge generation layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied substances can be synthesized.

In addition, by introducing various substituents into the structure of Formula 1, it is possible to finely control the energy band gap, while improving the properties at the interface between organic materials and diversifying the use of the material.

On the other hand, the heterocyclic compound has a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.

The heterocyclic compound according to an exemplary embodiment of the present application may be prepared by a multi-step chemical reaction. Some intermediate compounds are prepared first, and the compound of Formula 1 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to an exemplary embodiment of the present application may be prepared based on Preparation Examples to be described later.

Another exemplary embodiment of the present application provides an organic light emitting device including the heterocyclic compound represented by Formula 1 above. The "organic light emitting device" may be expressed in terms such as "organic light emitting diode", "OLED (Organic Light Emitting Diodes)", "OLED device", "organic electroluminescent device", and the like.

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

Specifically, the organic light emitting device according to an exemplary embodiment of the present application includes a first electrode, a second electrode, and one or more organic material layers provided between the first and second electrodes, and at least one of the organic material layers. includes a heterocyclic compound represented by Formula 1 above. When the heterocyclic compound represented by Formula 1 is included in the organic material layer, the luminous efficiency and lifespan of the organic light-emitting device are excellent.

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

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

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

In the exemplary embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound according to Formula 1 may be used as a material of the red organic light emitting device.

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

In addition, the organic material layer includes one or more emission layers, and the emission layer includes the heterocyclic compound represented by Formula 1 above. When the heterocyclic compound represented by Formula 1 is included in the light emitting layer of the organic material layer, the luminous efficiency and lifespan of the organic light emitting device are more excellent.

In an exemplary embodiment of the present application, the heterocyclic compound according to Formula 1 may be used as an N-type host.

In addition, in the organic light emitting device of the present application, the organic material layer may further include a heterocyclic compound represented by the following formula (2).

[Formula 2]

In Formula 2,

R24 and R25 are the same as or different from each other, and each independently -SiR101R102R103; a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

R26 and R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C 3 to C 60 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; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiR101R102R103; -P(=O)R104R105; and -NR106R107, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or a hetero ring, wherein R101 to R107 are the same as or different from each other, and each independently Hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

r and s are integers from 0 to 7, and when r is 2 or more, R26 is the same as or different from each other, and when s is 2 or more, R27 is the same as or different from each other.

In an exemplary embodiment of the present application, R26 and R27 of Formula 2 are the same as or different from each other, and each independently hydrogen; or deuterium.

In an exemplary embodiment of the present application, R26 and R27 are both hydrogen.

In an exemplary embodiment of the present application, R26 and R27 are both deuterium.

In another exemplary embodiment, R24 and R25 of Formula 2 are the same as or different from each other, and each independently -SiR101R102R103; a substituted or unsubstituted C 6 to C 40 aryl group; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms.

In another exemplary embodiment, R24 and R25 are the same as or different from each other, and each independently -SiR101R102R103; a substituted or unsubstituted C6-C20 aryl group; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

In another exemplary embodiment, R24 and R25 are the same as or different from each other, and each independently -SiR101R102R103; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; Or it may be a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, R24 and R25 are the same as or different from each other, and each independently -SiR101R102R103; phenyl group; biphenyl group; terphenyl group; triphenylene group; a fluorenyl group substituted with one or more selected from the group consisting of an alkyl group having 1 to 10 carbon atoms; or a naphthyl group.

wherein R101 to R103 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present application, Chemical Formula 2 may be represented by any one of the following compounds, but is not limited thereto.

In addition, the organic material layer includes one or more light emitting layers, the light emitting layer includes the heterocyclic compound represented by Formula 1 as a first compound, and one of the heterocyclic compounds represented by Formula 2 as a second compound. include When the heterocyclic compound represented by Formula 1 is included in the light emitting layer of the organic material layer, the luminous efficiency and lifespan of the organic light emitting device are more excellent.

In an exemplary embodiment of the present application, the heterocyclic compound according to Formula 2 may be used as a P-type host.

In addition, by introducing various substituents into the structure of Formula 2, a compound having intrinsic properties of the introduced substituent may be synthesized. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, an electron transport layer material, and a charge generation layer material used in manufacturing an organic light emitting device into the core structure, the conditions required for each organic material layer are satisfied substances can be synthesized.

In addition, by introducing various substituents into the structure of Formula 2, it is possible to finely control the energy band gap, while improving the properties at the interface between organic materials and diversifying the use of the material.

On the other hand, the heterocyclic compound has a high glass transition temperature (Tg) and excellent thermal stability. This increase in thermal stability is an important factor in providing driving stability to the device.

The heterocyclic compound according to an exemplary embodiment of the present application may be prepared by a multi-step chemical reaction. Some intermediate compounds are prepared first, and the compound of Formula 2 can be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to an exemplary embodiment of the present application may be prepared based on Preparation Examples to be described later.

In addition, the organic material layer includes one or more light emitting layers, and the light emitting layer further includes one of a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2 above. When one of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 is included in the light emitting layer of the organic material layer, the luminous efficiency and lifespan of the organic light emitting device are more excellent due to the exciplex phenomenon Do.

In the organic light emitting device of the present application, the organic material layer may include a light emitting layer, and the light emitting layer may include the heterocyclic compound as a host material of the light emitting material.

In the organic light emitting device of the present application, the light emitting layer may include two or more host materials, and at least one of the host materials may include the heterocyclic compound as a host material of the light emitting material.

In the organic light emitting device of the present application, the light emitting layer may be used by pre-mixing two or more host materials, and at least one of the two or more host materials uses the heterocyclic compound as a host material of the light emitting material may include

The pre-mixed means that the light emitting layer is mixed with two or more host materials before depositing them on the organic material layer and put it in one park.

In the organic light emitting device of the present application, the light emitting layer may include two or more host materials, each of the two or more host materials includes one or more p-type host materials and n-type host materials, and at least one of the host materials One may include the heterocyclic compound as a host material of the light emitting material. In this case, driving, efficiency, and lifespan of the organic light emitting diode may be improved.

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, a hole auxiliary layer, and a hole blocking layer.

The organic light emitting device according to an exemplary embodiment of the present application may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except for forming an organic material layer using the above-described heterocyclic compound.

In addition, another exemplary embodiment of the present application provides a composition for an organic material layer of an organic light emitting device that simultaneously includes one of the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 above.

In another exemplary embodiment of the present application, the weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 2 in the composition may be 1: 10 to 10: 1, and 1: 8 to 8: It may be 1, it may be 1: 5 to 5: 1, it may be 1: 2 to 2: 1, but is not limited thereto.

Specific details of the heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 included in the composition for the organic layer are the same as described above.

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

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

3 illustrates a case in which the organic material layer is multi-layered. The organic light emitting diode according to FIG. 3 includes a hole injection layer 301 , a hole transport layer 302 , a light emitting layer 303 , a hole blocking layer 304 , an electron transport layer 305 , and an electron injection layer 306 . However, the scope of the present application is not limited by such a laminated structure, and if necessary, the remaining layers except for the light emitting layer may be omitted, and other necessary functional layers may be further added.

In the organic light emitting device according to an exemplary embodiment of the present application, materials other than the heterocyclic compound of Formula 1 are exemplified below, but these are for illustration only and not for limiting the scope of the present application, may be substituted with known materials.

Materials having a relatively large work function may be used as the anode material, and transparent conductive oxides, metals, conductive polymers, or the like may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

Materials having a relatively low work function may be used as the anode material, and a metal, metal oxide, conductive polymer, or the like may be used. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

As the hole injection material, a known hole injection material may be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or Advanced Material, 6, p.677 (1994). starburst-type amine derivatives such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m- MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/Dodecylbenzenesulfonic acid or poly( 3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), polyaniline/Camphor sulfonic acid or polyaniline/ Poly(4-styrenesulfonate) (Polyaniline/Poly(4-styrene-sulfonate)) and the like may be used.

A pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used as a hole transport material, and a low molecular weight or high molecular material may be used.

Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone Derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, etc. may be used, and polymer materials as well as low molecular weight materials may be used.

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

A red, green, or blue light emitting material may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. In addition, although a fluorescent material can be used as a light emitting material, it can also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used alone, but materials in which the host material and the dopant material together participate in light emission may be used.

The organic light emitting device according to the exemplary embodiment of the present application may be a top emission type, a back emission type, or a double side emission type depending on a material used.

The heterocyclic compound according to an exemplary embodiment of the present application may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoreceptor, and an organic transistor.

Hereinafter, the present specification will be described in more detail through examples, but these are only for illustrating the present application and not for limiting the scope of the present application.

<Preparation Example 1> Preparation of compound 1-1

1) Preparation of compound 1-1-4

2,9-dichlorobenzofuro[3,2-d]pyrimidine (2,9-dichlorobenzofuro[3,2-d]pyrimidine) 20.0g (83.0mM), bis(pinacolato)diboron (bis(pinacolato) ) diboron) 42.2 g (166.0 mM), Pd(dba) ₂ 4.8 g (8.3 mM), XPhos 7.9 g (16.6 mM), and potassium acetate (KOAc) 24.4 g (249.0 mM) 1,4- It was dissolved in 700 mL of dioxane (1,4-dioxane) and refluxed for 12 hours. After the reaction was completed, distilled water and dichloromethane (hereinafter, DCM) were added and extracted at room temperature, and the organic layer was dried over MgSO ₄ , and then the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:5) to obtain 20.9 g (76%) of Compound 1-1-4.

The Hex means hexane (Hexane).

2) Preparation of compound 1-1-3

Compound 1-1-4 20.0 g (60.0 mM), 1-bromodibenzo [b, d] furan (1-bromodibenzo [b, d] furan) 14.8 g (60.0 mM), Pd (PPh) ₄ 3.5 g ( 3.0 mM), and 16.6 g (120.0 mM) of K ₂ CO ₃ were dissolved in 1,4-dioxane/water (1,4-dioxane/H ₂ O) 350/70 mL and refluxed for 10 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 16.7 g (75%) of compound 1-1-3.

3) Preparation of compound 1-1-2

Compound 1-1-3 16.0 g (43.0 mM), bis (pinacolato) diboron (bis (pinacolato) diboron) 21.8 g (86.0 mM), Pd (dba) ₂ 2.5 g (4.3 mM), XPhos 4.1 g (8.6 mM), and 12.7 g (129.0 mM) of KOAc were dissolved in 400 mL of 1,4-dioxane and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:4) to obtain 13.9 g (70%) of compound 1-1-2.

4) Preparation of target compound 1-1

Compound 1-1-2 13.0 g (28.0 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) 7.5 g (28.0 mM), Pd (PPh) ₄ 1.6 g (1.4 mM), K ₂ CO ₃ 7.7 g (56.0 mM) 1,4-dioxane / water (1,4-dioxane / H ₂ O) 200 Dissolved in /40mL and refluxed for 10 hours After completion of the reaction, distilled water and DCM were added at room temperature for extraction, the organic layer was dried over MgSO ₄ , and the solvent was removed using a rotary evaporator. 1:3) and recrystallized with methanol to obtain 11.3 g (71%) of the target compound 1-1.

Using the compound S of Table 1 below instead of 2,9-dichlorobenzofuro [3,2-d] pyrimidine in Preparation Example 1, 1-bro Intermediate A of Table 1 was used instead of modibenzo[b,d]furan (1-bromodibenzo[b,d]furan) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2 -chloro-4,6-diphenyl-1,3,5-triazine) was prepared in the same manner as in Preparation Example 1 except for using the intermediate B of Table 1 below to synthesize the target compound A.

<Preparation Example 2> Preparation of compound 1-51

1) Preparation of compound 1-51-3

2,9-dichlorobenzofuro [3,2-d] pyrimidine (2,9-dichlorobenzofuro [3,2-d] pyrimidine) 20.0 g (83.0 mM), 9H-carbazole (9H-carbazole) 13.9 g ( 83.0 mM), and K ₂ CO ₃ 22.9 g (166.0 mM) were dissolved in 350 mL of dimethylformamide (hereinafter, DMF) and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) to obtain 23.0 g (75%) of compound 1-51-3.

2) Preparation of compound 1-51-2

Compound 1-51-3 23.0 g (62.0 mM), bis (pinacolato) diboron (bis (pinacolato) diboron) 31.5 g (124.0 mM), Pd (dba) ₂ 3.6 g (6.2 mM), XPhos 5.9 g (12.4 mM), and 18.3 g (186.0 mM) of KOAc were dissolved in 550 mL of 1,4-dioxane and refluxed for 10 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:4) to obtain 20.6 g (72%) of compound 1-51-2.

3) Preparation of target compound 1-51

Compound 1-51-2 20.0 g (43.0 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) ) 11.5 g (43.0 mM), Pd(PPh) ₄ 2.5 g (2.2 mM), and K ₂ CO ₃ 11.9 g (86.0 mM) 1,4-dioxane / water (1,4-dioxane / H ₂ O ) was dissolved in 350/70 mL and refluxed for 10 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 17.3 g (71%) of the target compound 1-51.

In Preparation Example 2, 2,9-dichlorobenzofuro [3,2-d] pyrimidine (2,9-dichlorobenzofuro [3,2-d] pyrimidine) was used in place of the compound S in Table 2 below, 9H-carba Intermediate A of Table 2 was used instead of sol (9H-carbazole) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3, 5-triazine) was prepared in the same manner as in Preparation Example 2, except that Intermediate B of Table 2 was used instead of to synthesize the target compound B.

<Preparation Example 3> Synthesis of compound 2-3

1) Preparation of compound 2-3

3-bromo-1,1'-biphenyl 3.7g (15.8mM), 9-phenyl-9H,9'H-3,3'-bicarbazole 6.5g (15.8mM), CuI 3.0g (15.8mM) ), 1.9 mL (15.8 mM) of trans-1,2-diaminocyclohexane, and 3.3 g (31.6 mM) of K ₃ PO ₄ were dissolved in 100 mL of 1,4-oxane and refluxed for 24 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO ₄ , and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 7.5 g (85%) of the target compound 2-3.

In Preparation Example 3, the intermediate A of Table 3 was used instead of 3-bromo-1,1′-biphenyl, and the 9-phenyl-9H,9′H-3,3′-bicarbazole was replaced with Table 3 The target compound C was synthesized in the same manner as in Preparation Example 3, except that Intermediate B was used.

The remaining compounds other than the compounds described in Tables 1 to 3 were prepared in the same manner as in the above-described Preparation Examples.

Synthesis confirmation results of the compounds prepared above are shown in Tables 4 and 5 below. Table 4 is a measurement value of ¹ H NMR (CDCl ₃ , 200Mz), Table 5 is a measurement value of the FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).

compound
number ¹ H NMR (CDCl ₃ , 200 Mz) 1-1 δ = 8.50(1H, s), 8.28(4H, d), 7.89(1H, d), 7.75(2H, d), 7.62-7.66(3H, m), 7.32-7.51(10H, m) 1-7 δ = 8.50(1H, s), 8.28(2H, d), 8.23(1H, s), 7.71-7.81(9H, m), 7.62(1H, d), 7.41-7.52(12H, m) 1-13 δ = 8.50(1H, s), 8.28(2H, d), 8.24(1H, d), 7.95(1H, d), 7.89(1H, d), 7.32-7.75(19H, m) 1-18 δ = 8.81(2H, d), 8.50(1H, s), 8.30(2H, d), 8.20(2H, s), 7.75-7.89(6H, m), 7.32-7.66(14H, m) 1-20 δ = 8.50 (2H, s), 8.24 (1H, d), 7.32-7.81 (17H, m) 1-21 δ = 8.50(1H, s), 8.45(1H, d), 8.23(1H, s), 7.98(1H, d), 7.94(1H, d), 7.75-7.82(6H, m), 7.41-7.62( 11H, m) 1-24 δ = 8.50(1H, s), 8.28(4H, d), 8.00(3H, s), 7.75-7.86(4H, m), 8.62(1H, d), 7.41-7.52(12H, m) 1-30 δ = 8.50(1H, s), 8.45(1H, d), 8.41(1H, d), 8.24(1H, d), 7.98(1H, d), 7.70-7.85(5H, m), 7.41-7.62( 17H, m), 7.25 (2H, d) 1-31 δ = 8.50(1H, s), 8.28(4H, d), 7.87(1H, d), 7.75(1H, d), 7.28-7.63(14H, m), 1.72(6H, s) 1-38 δ = 8.50(1H, s), 8.30(4H, d), 8.20(2H, s), 7.87(1H, d), 7.83(1H, d), 7.75(1H, d), 7.38-7.62(12H, m), 7.28 (1H, t), 1.72 (6H, s) 1-41 δ = 8.55(1H, d), 8.50(1H, s), 8.23(1H, s), 7.94(1H, d), 7.79(5H, d), 7.75(1H, d), 7.25-7.62(17H, m) 1-45 δ = 8.55(1H, d), 8.50(1H, s), 7.85-7.94(6H, m), 7.25-7.75(26H, m) 1-51 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.12(1H, d), 7.94(1H, d), 7.55(1H, d), 7.63(1H, d) , 7.62 (1H, d), 7.25-7.51 (11H, m) 1-54 δ = 8.87(1H, s), 8.55(1H, d), 8.18-8.28(4H, m), 7.94(1H, d), 7.79(3H, d), 7.75(1H, d), 7.62(2H, d), 7.41-7.52 (14H, m) 1-60 δ = 8.87(1H, s), 8.55(1H, d), 8.50(1H, s), 7.94(1H, d), 7.87(1H, d), 7.62-7.77(6H, m), 7.25-7.52( 10H, m) 1-61 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 7.94(1H, d), 7.89(2H, d), 7.75(1H, d), 7.66(1H, d) , 7.62 (1H, d), 7.25-7.51 (12H, m) 1-63 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 7.94(1H, d), 7.89(1H, d), 7.75(1H, d), 7.25-7.66(15H, m) 1-65 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 7.94(1H, d), 7.89(1H, d), 7.75(1H, d), 7.66(1H, d) , 7.62 (1H, d), 7.25-7.51 (13H, m) 1-75 δ = 8.87(1H, s), 8.55(1H, d), 8.45(1H, d), 8.28(4H, d), 7.98(1H, d), 7.94(1H, d), 7.86(1H, s) , 7.78 (1H, s), 7.75 (1H, d), 7.62 (1H, d), 7.25-7.52 (11H, m) 1-77 δ = 8.87(1H, s), 8.55(1H, d), 8.45(1H, d), 8.28(4H, d), 7.98(2H, d), 7.94(1H, d), 7.75(1H, d) , 7.62 (1H, d), 7.25-7.52 (12H, m) 1-81 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.09(1H, d), 8.00(1H, d), 7.94(1H, d), 7.75(1H, d) , 7.71(1H, d), 7.62(1H, d), 7.61(1H, d), 7.24-751(11H, m), 1.72(6H, s) 1-87 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.09(1H, d), 7.94(1H, d), 7.75(1H, d), 7.62(1H, d) , 7.61 (1H, d), 7.24-7.52 (13H, m), 1.72 (6H, s) 1-90 δ = 8.87(1H, s), 8.55(1H, d), 8.28(2H, d), 8.24(1H, d), 8.09(1H, d), 7.94(1H, d), 7.70-7.79(3H, m), 7.24-7.61 (18H, m), 1.72 (6H, s) 1-91 δ = 8.87(1H, s), 8.55(2H, d), 8.28(4H, d), 8.12(1H, d), 7.94(2H, d), 7.75(1H, d), 7.25-7.62(18H, m) 1-93 δ = 8.87(1H, s), 8.55(2H, d), 8.28(4H, d), 8.12(1H, d), 7.94(2H, d), 7.75(1H, d), 7.25-7.62(18H, m) 1-101 δ = 8.50(1H, s), 8.28(4H, d), 7.89(1H, d), 7.62-7.81(6H, m), 7.32-751(9H, m) 1-102 δ = 8.50(1H, s), 8.28(4H, d), 7.71-7.81(7H, m), 7.62(1H, d), 7.41-7.52(12H, m) 1-108 δ = 8.50(1H, s), 8.23-8.30(5H, m), 7.81-7.89(5H, m), 7.66-7.72(5H, m), 7.32-7.52(10H, m) 1-114 δ = 8.50(1H, s), 8.24(1H, d), 7.25-7.85(27H, m) 1-119 δ = 8.81 (2H, d), 8.50(1H, s), 8.32(1H, d), 8.22(1H, s), 8.20(2H, s), 7.66-7.89(8H, m), 7.32-7.57( 16H, m) 1-122 δ = 8.50(1H, s), 8.45(1H, d), 8.28(2H, d), 8.23(1H, s), 7.98(1H, d), 7.94(1H, d), 7.70-7.82(6H, m), 7.41-7.57 (13H, m) 1-125 δ = 8.50(1H, s), 8.45(1H, d), 8.00(1H, s), 7.98(1H, d), 7.80-7.86(7H, m), 7.72(1H, d), 7.71(1H, s), 7.41-7.52 (12H, m), 7.25 (4H, d) 1-132 δ = 8.50(1H, s), 8.24(2H, d), 8.87(1H, d), 8.81(1H, d), 7.72(1H, d), 7.71(1H, s), 7.70(2H, s) , 7.28-7.63 (20H, m), 1.72 (6H, s) 1-133 δ = 8.50(1H, s), 8.23(1H, s), 8.06(1H, s), 7.71-7.87(8H, m), 7.51-7.61(7H, m), 7.41(2H, t), 7.38( 1H, t), 7.28 (1H, t), 1.72 (6H, s) 1-136 δ = 8.50(1H, s), 8.28(4H, d), 7.93(2H, d), 7.71-7.81(5H, m), 7.63(2H, d), 7.41-7.52(11H, m), 1.72( 6H, s) 1-143 δ = 8.55(1H, d), 8.50(1H, s), 8.28(2H, d), 8.23(1H, s), 7.94(1H, d), 7.71-7.85(8H, m), 7.25-7.59( 17H, m) 1-146 δ = 8.55(1H, d), 8.50(1H, s), 8.32(1H, d), 8.30(2H, d), 8.18-8.22(4H, m), 7.94(1H, d), 7.79(1H, d), 7.75 (1H, d), 7.25-7.62 (16H, m) 1-149 δ = 8.50(1H, s), 8.49(1H, d), 8.28(4H, d), 8.10(1H, d), 8.08(1H, d), 7.87(1H, d), 7.81(1H, d) , 7.72(1H, d), 7.71(1H, s), 7.35-7.62(18H, m) 1-152 δ = 8.87(1H, s), 8.55(1H, d), 8.12(1H, d), 7.94(1H, d), 7.85(4H, d), 7.81(1H, d), 7.72(1H, d) , 7.71 (1H, s), 7.63 (1H, d), 7.25-7.52 (18H, m) 1-155 δ = 8.87(1H, s), 8.55(1H, d), 8.18-8.28(4H, m), 7.94(1H, d), 7.70-7.81(6H, m), 7.25-7.62(18H, m) 1-162 δ = 8.87(1H, s), 8.55(1H, d), 8.30(2H, d), 8.23(1H, s), 7.71-7.94(11H, m), 7.25-7.53(13H, m) 1-164 δ = 8.87(1H, s), 8.55(1H, d), 8.28(2H, d), 8.24(1H, d), 7.94(1H, d), 7.89(1H, d), 7.81(1H, d) , 7.25-7.72 (20H, m) 1-167 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 7.94(1H, d), 7.89(1H, d), 7.81(1H, d), 7.66-7.72(3H, m), 7.25-7.52 (12H, m) 1-176 δ = 8.87(1H, s), 8.81(2H, d), 8.55(1H, d), 8.45(1H, d), 8.32(1H, d), 8.22(1H, s), 8.20(2H, s) , 7.86-7.98 (5H, m), 7.78 (1H, s), 7.75 (1H, d), 7.25-7.52 (18H, m) 1-179 δ = 8.87(1H, s), 8.55(1H, d), 8.45(1H, d), 8.28(4H, d), 8.05(1H, d), 7.98(1H, d), 7.94(1H, d) , 7.81 (1H, d), 7.72 (1H, d), 7.71 (1H, s), 7.25-7.52 (11H, m) 1-183 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.09(1H, d), 8.00(1H, d), 7.94(1H, d), 7.81(1H, d) , 7.72(1H, d), 7.71(1H, s), 7.61(1H, d), 7.25-7.51(11H, m), 1.72(6H, s) 1-188 δ = 8.87(1H, s), 8.55(1H, d), 8.28(2H, d), 8.09(1H, d), 7.94(1H, d), 7.85(2H, d), 7.81(1H, d) , 7.72(1H, d), 7.71(1H, s), 7.61(1H, d), 7.25-7.52(16H, m), 1.72(6H, s) 1-192 δ = 8.87(1H, s), 8.55(2H, d), 8.28(2H, d), 8.12(1H, d), 7.94(2H, d), 7.85(2H, d), 7.81(1H, d) , 7.72 (1H, d), 7.71 (1H, s), 7.25-7.58 (20H, m) 1-195 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.12(1H, d), 7.94(1H, d), 7.81(1H, d), 7.72(1H, d) , 7.71 (1H, s), 7.25-7.63 (18H, m) 1-200 δ = 8.87(1H, s), 8.55(2H, d), 8.28(4H, d), 8.12(1H, d), 7.94(2H, d), 7.81(1H, d), 7.72(1H, d) , 7.71 (1H, s), 7.25-7.59 (16H, m) 1-201 δ = 8.50(1H, s), 8.28(4H, d), 7.95(1H, d), 7.89(1H, d), 7.75(2H, d), 7.66(1H, d), 7.64(1H, s) , 7.62 (1H, d), 7.32-7.51 (9H, m) 1-203 δ = 8.50(1H, s), 8.28(2H, d), 8.24(1H, d), 7.95(1H, d), 7.89(1H, d), 7.32-7.75(19H, m) 1-209 δ = 8.50(1H, s), 8.30(4H, d), 8.23(1H, s), 7.64-7.95(12H, m), 7.32-7.52(12H, m) 1-215 δ = 8.50(1H, s), 8.28(4H, d), 7.85-7.95(5H, m), 7.75(2H, d), 7.66(1H, d), 7.64(2H, s), 7.25-7.512( 10H, m) 1-220 δ = 8.50 (2H, s), 8.24 (1H, d), 7.32-7.95 (17H, m) 1-223 δ = 8.50(1H, s), 8.45(1H, d), 8.28(2H, d), 8.23(1H, s), 7.98(1H, d), 7.95(1H, d), 7.94(1H, d) , 7.75-7.85(6H, m), 7.64(1H, s), 7.41-7.56(9H, m), 8.25(2H, d) 1-226 δ = 8.50(1H, s), 8.45(1H, d), 8.08-8.30(8H, m), 7.98(2H, d), 7.82(1H, d), 7.41-7.54(10H, m) 1-234 δ = 8.50(1H, s), 8.30(2H, d), 8.28(2H, d), 8.23(1H, s), 8.06(1H, s), 7.95(1H, d), 7.87(1H, d) , 7.85(2H, d), 7.75(1H, d), 7.38-7.61(13H, m), 7.28(1H, t), 1.72(6H, s) 1-237 δ = 8.50(1H, s), 8.24(1H, d), 7.85-7.95(5H, m), 7.70-7.77(3H, m), 7.38-7.63(16H, m), 7.25(2H, d), 7.28 (1H, t), 1.72 (6H, s) 1-240 δ = 8.50(2H, s), 8.24(1H, d), 7.95(1H, d), 7.87(1H, d), 7.83(1H, d), 7.28-7.70(14H, m), 1.72(6H, s) 1-244 δ = 8.50(1H, s), 8.28(4H, d), 8.18(1H, d), 8.00(1H, d), 7.95(1H, d), 7.87(1H, d), 7.41-7.77(21H, m) 1-247 δ = 8.55(1H, d), 8.50(1H, s), 8.18-8.30(7H, m), 7.95(1H, d), 7.94(1H, d), 7.79(1H, d), 7.75(1H, d), 7.25-7.64 (19H, m), 1-249 δ = 8.50(1H, s), 8.28(4H, d), 8.18(1H, d), 8.08(1H, d), 8.00(1H, d), 7.95(1H, d), 7.87(1H, d) , 7.77(1H, s), 7.75(1H, d), 7.35-7.58(18H, m) 1-251 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.12(1H, d), 7.95(1H, d), 7.94(1H, d), 7.75(1H, d) , 7.64 (1H, s), 7.63 (1H, d), 7.25-7.51 (10H, m) 1-254 δ = 8.87(1H, s), 8.55(1H, d), 8.28(2H, d), 8.23(1H, s), 8.18(1H, d), 7.95(1H, d), 7.94(1H, d) , 7.79(3H, d), 7.75(1H, d), 7.64 (1H, s), 7.62 (1H, s), 7.25-7.52(13H, m) 1-263 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 7.95(1H, d), 7.94(1H, d), 7.89(1H, d), 7.75(1H, d) , 7.25-7.66 (14H, m) 1-268 δ = 8.87(1H, s), 8.55(1H, d), 7.85-7.95(7H, m), 7.75(1H, d), 7.66(1H, d), 7.64(1H, s), 7.25-7.52( 20H, m) 1-270 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 7.95(1H, d), 7.94(1H, d), 7.89(2H, d), 7.75(1H, d) , 7.66(1H, d), 7.64(1H, s), 7.25-7.51(10H, m), 7.13(1H, d) 1-273 δ = 8.87(1H, s), 8.55(1H, d), 8.45(1H, d), 8.28(4H, d), 7.98(1H, d), 7.95(1H, d), 7.94(1H, d) , 7.86(1H, s), 7.78(1H, s), 7.75(1H, d), 7.64(1H, s), 7.25-7.52(10H, m) 1-280 δ = 8.87(1H, s), 8.55(1H, d), 8.45(1H, d), 8.24(1H, d), 8.05(1H, d), 7.98(1H, d), 7.95(1H, d) , 7.94(1H, d), 7.85(2H, d), 7.75(1H, d), 7.70(1H, s), 7.25-7.64(20H, m) 1-284 δ = 8.87(1H, s), 8.55(1H, d), 8.09-8.26(7H, m), 7.94-8.00(3H, m), 7.70(1H, s), 7.24-7.61(21H, m), 1.72 (6H, s) 1-289 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.09(1H, d), 7.95(1H, d), 7.94(1H, d), 7.79(1H, d) , 7.75(1H, d), 7.64(1H, s), 7.61(1H, d), 7.24-751(11H, m), 1.72(6H, s) 1-293 δ = 8.87(1H, s), 8.55(2H, d), 8.28(4H, d), 8.12(1H, d), 7.95(1H, d), 7.94(2H, d), 7.75(1H, d) , 7.25-7.58 (17H, m) 1-296 δ = 8.87(1H, s), 8.81(2H, d), 8.55(1H, d), 8.12-8.26(5H, m), 7.98(1H, d), 7.94(1H, d), 7.88(2H, d), 7.70 (1H, s), 7.25-7.63 (25H, m) 1-298 δ = 8.87(1H, s), 8.55(2H, d), 8.23(1H, s), 7.95(1H, d), 7.94(2H, d), 7.79(4H, d), 7.75(1H, d) , 7.25-7.63 (18H, m) 1-301 δ = 8.28(4H, d), 7.89(1H, d), 7.75(1H, d), 7.66(1H, d), 7.62(1H, d), 7.38-7.51(9H, m) 1-304 δ = 8.50(1H, s), 8.24(2H, d), 7.89(1H, d), 7.32-7.70 (25H, m) 1-310 δ = 8.50(1H, s), 8.28(2H, d), 8.24(1H, d), 8.23(1H, s), 7.89(1H, d), 7.32-7.81(20H, m) 1-316 δ = 8.50(1H, s), 8.30(2H, d), 8.20(2H, s), 8.13(1H, d), 7.89(1H, d), 7.85(1H, d), 7.81(1H, d) , 7.72 (1H, d), 7.66 (1H, d), 7.32-7.54 (12H, m) 1-320 δ = 8.50(2H, s), 8.24(1H, d), 7.81-7.89(4H, m), 7.57-7.70(6H, m), 7.32-7.48(7H, m) 1-324 δ = 8.50(1H, s), 8.28(4H, d), 8.00(3H, d), 7.86(2H, d), 7.80(1H, d), 7.81(1H, d), 7.66(1H, d) , 7.38-7.52 (12H, m) 1-327 δ = 8.50(1H, s), 8.45(1H, d), 8.30(2H, d), 8.20(2H, s), 8.13(1H, d), 8.11(1H, d), 8.08(1H, s) , 7.98(1H, d), 7.82(1H, d), 7.72(1H, d), 7.70(1H, s), 7.41-7.57(14H, m) 1-330 δ = 8.50(1H, s), 8.45(1H, d), 8.41(1H, d), 8.24(1H, d), 7.98(1H, d), 7.85(2H, d), 7.81(1H, d) , 7.80(1H, d), 7.70(1H, s), 7.66(1H, d), 7.38-7.58(16H, m), 7.25(2H, d) 1-335 δ = 8.50(1H, s), 8.28(2H, d), 8.24(1H, d), 8.23(1H, s), 8.06(1H, s), 7.87(1H, d), 7.79(2H, d) , 7.38-7.70 (16H, m), 7.28 (1H, t), 1.72 (6H, s) 1-338 δ = 8.50(1H, s), 8.30(4H, d), 8.20(2H, s), 7.87(1H, d), 7.83(1H, d), 7.81(1H, d), 7.66(1H, d) , 7.38-7.55 (11H, m), 7.28 (1H, t), 1.72 (6H, s) 1-341 δ = 8.55(1H, d), 8.50(1H, s), 8.23(1H, s), 7.94(1H, d), 7.81(1H, d), 7.79(5H, d), 7.25-7.66(17H, m) 1-348 δ = 8.55(1H, d), 8.50(2H, s), 8.18(1H, d), 7.79-7.94(5H, m), 7.25-7.66(16H, m) 1-351 δ = 8.87(1H, s), 7.81(1H, d), 7.66(1H, d), 7.38(1H, t) 1-352 δ = 8.87(1H, s), 8.55(1H, d), 8.12(1H, d), 7.94(1H, d), 7.85(4H, d), 7.81(1H, d), 7.66(1H, d) , 7.63 (1H, d), 7.25-7.52 (19H, m) 1-354 δ = 8.87(1H, s), 8.55(1H, d), 8.28(2H, d), 8.23(1H, s), 8.18(1H, d), 7.94(1H, d), 7.79(3H, d) , 7.66 (1H, d), 7.62 (2H, d), 7.25-7.52 (14H, m) 1-364 δ = 8.87(1H, s), 8.55(1H, d), 8.28(2H, d), 8.24(1H, d), 7.94(1H, d), 7.89(1H, d), 7.81(1H, d) , 7.25-7.70 (20H, m) 1-369 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 7.94(1H, d), 7.89(1H, d), 7.81(1H, d), 7.66(3H, d) , 7.19-7.51 (12H, m) 1-371 δ = 8.87(1H, s), 8.55(1H, d), 8.45(1H, d), 8.28(4H, d), 8.05(1H, d), 7.98(1H, d), 7.94(1H, d) , 7.81 (1H, d), 7.25-7.66 (13H, m) 1-374 δ = 8.87(1H, s), 8.55(1H, d), 8.45(1H, d), 8.30(2H, d), 8.24(1H, d), 8.23(1H, s), 7.98(1H, d) , 7.94(1H, d), 7.86(1H, s), 7.85(2H, d), 7.78(1H, s), 7.25-7.66(20H, m) 1-379 δ = 8.87(1H, s), 8.55(1H, d), 8.45(1H, d), 8.28(4H, d), 8.05(1H, d), 7.98(1H, d), 7.94(1H, d) , 7.81 (1H, d), 7.66 (1H, d), 7.25-7.52 (12H, m) 1-383 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.09(1H, d), 8.00(1H, d), 7.94(1H, d), 7.81(1H, d) , 7.66 (1H, d), 7.61 (1H, d), 7.24-7.51 (12H, m), 1.72 (6H, s) 1-386 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.12(1H, s), 8.09(1H, d), 7.94(1H, d), 7.81(1H, d) , 7.66(1H, d), 7.61(1H, d), 7.24-7.54(12H, m), 1.72(6H, s) 1-390 δ = 8.87(1H, s), 8.55(1H, d), 8.28(2H, d), 8.24(1H, d), 8.09(1H, d), 7.94(1H, d), 7.81(1H, d) , 7.79 (1H, d), 7.24-7.66 (19H, m), 1.72 (6H, s) 1-395 δ = 8.87(1H, s), 8.55(1H, d), 8.28(4H, d), 8.12(1H, d), 7.94(1H, d), 7.81(1H, d), 7.25-7.66(20H, m) 1-399 δ = 8.87(1H, s), 8.55(2H, d), 8.24(2H, d), 7.94(2H, d), 7.81(1H, d), 7.25-7.70(29H, m) 2-3 δ = 8.55(1H, d), 8.30(1H, d), 8.21-8.13(3H, m), 7.99-7.89(3H, m), 7.77-7.35(17H, m), 7.20-7.16(2H, m) ) 2-4 δ = 8.55(1H, d), 8.30(1H, d), 8.19-8.13(2H, m), 7.99-7.89(8H, m), 7.77-7.75(3H, m), 7.62-7.35(11H, m) ), 7.20-7.16 (2H, m) 2-7 δ = 8.55(1H, d), 8.31-8.30(3H, d), 8.19-8.13(2H, m), 7.99-7.89(5H, m), 7.77-7.75(5H, m), 7.62-7.35(14H) , m), 7.20-7.16 (2H, m) 2-31 δ = 8.55(1H, d), 8.30(1H, d), 8.21-8.13(4H, m), 7.99-7.89(4H, m), 7.77-7.35(20H, m), 7.20-7.16(2H, m) ) 2-32 δ = 8.55(1H, d), 8.30(1H, d), 8.21-8.13(3H, m), 7.99-7.89(8H, m), 7.77-7.35(17H, m), 7.20-7.16(2H, m) ) 2-42 δ = 8.55(1H, d), 8.30(1H, d), 8.19(1H, d), 8.13(1H, d), 7.99-7.89(12H, m), 7.77-7.75(5H, m), 7.58( 1H, d), 7.49-7.35 (8H, m), 7.20-7.16 (2H, m)

compound FD-MS compound FD-MS 1-1 m/z=567.17 (C ₃₇ H ₂₁ N ₅ O ₂ =567.59) 1-7 m/z= 642.21 (C ₄₄ H ₂₆ N ₄ O ₂ =642.70) 1-13 m/z= 643.20 (C ₄₃ H ₂₅ N ₅ O ₂ =643.69) 1-18 m/z= 641.21 (C ₄₃ H ₂₇ N ₃ O ₂ =641.71) 1-20 m/z= 580.15 (C ₃₈ H ₂₀ N ₄ O ₃ =580.59) 1-21 m/z= 582.15 (C ₃₈ H ₂₂ N ₄ OS=582.67) 1-24 m/z= 659.18 (C ₄₃ H ₂₅ N ₅ OS=659.76) 1-30 m/z= 735.21 (C ₄₉ H ₂₉ N ₅ OS=735.85) 1-31 m/z= 593.22 (C ₄₀ H ₂₇ N ₅ O=593.68) 1-38 m/z=591.23 (C ₄₂ H ₂₉ N ₃ O=591.70) 1-41 m/z= 641.22 (C ₄₄ H ₂₇ N ₃ O=641.72) 1-45 m/z= 794.28 (C ₅₅ H ₃₄ N ₆ O=794.90) 1-51 m/z= 566.19 (C ₃₇ H ₂₂ N ₆ O=566.61) 1-54 m/z= 641.22 (C ₄₄ H ₂₇ N ₅ O=642.72) 1-60 m/z= 579.17 (C ₃₈ H ₂₁ N ₅ O ₂ =579.61) 1-61 m/z= 656.20 (C ₄₃ H ₂₄ N ₆ O ₂ =656.69) 1-63 m/z= 656.20 (C ₄₃ H ₂₄ N ₆ O ₂ =656.69) 1-65 m/z= 656.20 (C ₄₃ H ₂₄ N ₆ O ₂ =656.69) 1-75 m/z = 672.17 (C ₄₃ H ₂₄ N ₆ OS=672.76) 1-77 m/z = 672.17 (C ₄₃ H ₂₄ N ₆ OS=672.76) 1-81 m/z= 682.25 (C ₄₆ H ₃₀ N ₆ O=682.77) 1-87 m/z= 682.25 (C ₄₆ H ₃₀ N ₆ O=682.77) 1-90 m/z= 758.28 (C ₅₂ H ₃₄ N ₆ O=758.87) 1-91 m/z= 731.24 (C ₄₉ H ₂₉ N ₇ O=731.80) 1-93 m/z= 731.24 (C ₄₉ H ₂₉ N ₇ O=731.80) 1-101 m/z=567.17 (C ₃₇ H ₂₁ N ₅ O ₂ =567.59) 1-102 m/z= 643.20 (C ₄₃ H ₂₅ N ₅ O ₂ =643.69) 1-108 m/z= 642.21 (C ₄₄ H ₂₆ N ₄ O ₂ =642.70) 1-114 m/z= 719.23 (C ₄₉ H ₂₉ N ₅ O ₂ =719.79) 1-119 m/z= 717.24 (C ₅₁ H ₃₁ N ₃ O ₂ =717.81) 1-122 m/z= 658.18 (C ₄₄ H ₂₄ N ₄ OS =658.77) 1-125 m/z= 735.21 (C ₄₉ H ₂₉ N ₅ OS=735.85) 1-132 m/z= 745.28 (C ₅₂ H ₃₅ N ₅ O=745.87) 1-133 m/z=592.23 (C ₄₁ H ₂₈ N ₄ O=592.69) 1-136 m/z= 669.25 (C ₄₆ H ₃₁ N ₅ O=669.77) 1-143 m/z= 717.25 (C ₅₁ H ₃₁ N ₅ O=717.81) 1-146 m/z= 640.23 (C ₄₅ H ₂₈ N ₄ O=640.73) 1-149 m/z= 718.25 (C ₄₉ H ₃₀ N ₆ O=718.80) 1-152 m/z= 718.25 (C ₄₉ H ₃₀ N ₆ O=718.80) 1-155 m/z= 717.25 (C ₅₁ H ₃₁ N ₅ O=717.81) 1-162 m/z= 731.23 (C ₅₀ H ₂₉ N ₅ O ₂ =731.80) 1-164 m/z= 732.23 (C ₄₉ H ₂₈ N ₆ O ₂ =732.79) 1-167 m/z= 656.20 (C ₄₃ H ₂₄ N ₆ O ₂ =656.69) 1-176 m/z= 822.25 (C ₅₇ H ₃₄ N ₄ OS=822.97) 1-179 m/z = 672.17 (C ₄₃ H ₂₄ N ₆ OS=672.76) 1-183 m/z= 682.25 (C ₄₆ H ₃₀ N ₆ O=682.77) 1-188 m/z= 758.28 (C ₅₂ H ₃₄ N ₆ O=758.87) 1-192 m/z= 807.27 (C ₅₅ H ₃₃ N ₇ O=807.90) 1-195 m/z= 731.24 (C ₄₉ H ₂₉ N ₇ O=731.80) 1-200 m/z= 731.23 (C ₄₉ H ₂₉ N ₇ O=731.80) 1-201 m/z=567.17 (C ₃₇ H ₂₁ N ₅ O ₂ =567.59) 1-203 m/z= 643.20 (C ₄₃ H ₂₅ N ₅ O ₂ =643.69) 1-209 m/z= 718.24 (C ₅₀ H ₃₀ N ₄ O ₂ =718.80) 1-215 m/z= 643.20 (C ₄₃ H ₂₅ N ₅ O ₂ =643.69) 1-220 m/z= 580.15 (C ₃₈ H ₂₀ N ₄ O ₃ =580.59) 1-223 m/z= 658.18 (C ₄₄ H ₂₄ N ₄ OS =658.77) 1-226 m/z= 581.16 (C ₃₉ H ₂₃ N ₃ OS=581.68) 1-234 m/z= 668.26 (C ₄₇ H ₃₂ N ₄ O =668.78) 1-237 m/z= 745.28 (C ₅₂ H ₃₅ N ₅ O=745.87) 1-240 m/z= 606.21 (C ₄₁ H ₂₆ N ₄ O ₂ =306.67) 1-244 m/z= 718.25 (C ₄₉ H ₃₀ N ₆ O=718.80) 1-247 m/z= 716.26 (C ₅₁ H ₃₂ N ₄ O=716.83) 1-249 m/z= 718.25 (C ₄₉ H ₃₀ N ₆ O=718.80) 1-251 m/z= 566.19 (C ₃₇ H ₂₂ N ₆ O=566.61) 1-254 m/z= 641.22 (C ₄₄ H ₂₇ N ₅ O=641.72) 1-263 m/z= 656.20 (C ₄₄ H ₂₇ N ₅ O=656.69) 1-268 m/z= 808.26 (C ₅₅ H ₃₂ N ₆ O ₂ =808.88) 1-270 m/z= 656.20 (C ₄₃ H ₂₄ N ₆ O ₂ =656.69) 1-273 m/z = 672.17 (C ₄₃ H ₂₄ N ₆ OS=672.76) 1-280 m/z= 824.24 (C ₅₅ H ₃₂ N ₆ OS=824.95) 1-284 m/z= 832.32 (C ₆₀ H ₄₀ N ₄ O=832.99) 1-289 m/z= 682.25 (C ₄₆ H ₃₀ N ₆ O=682.77) 1-293 m/z= 731.24 (C ₄₉ H ₂₉ N ₇ O=731.80) 1-296 m/z= 881.32 (C ₆₃ H ₃₉ N ₅ O=882.02) 1-298 m/z= 730.25 (C ₅₀ H ₃₀ N ₆ O=730.81) 1-301 m/z = 571.19 (C ₃₇ H ₁₇ D ₄ N ₅ O ₂ =571.62) 1-304 m/z= 719.23 (C ₄₉ H ₂₉ N ₅ O ₂ =719.79) 1-310 m/z= 642.21 (C ₄₄ H ₂₆ N ₄ O ₂ =642.70) 1-316 m/z= 565.18 (C ₃₉ H ₂₃ N ₃ O ₂ =565.62) 1-320 m/z= 580.15 (C ₃₈ H ₂₀ N ₄ O ₃ =580.59) 1-324 m/z= 659.18 (C ₄₅ H ₂₅ N ₅ OS=659.76) 1-327 m/z= 657.19 (C ₄₅ H ₂₇ N ₃ OS=657.78) 1-330 m/z= 735.21 (C ₄₉ H ₂₉ N ₅ OS=735.85) 1-335 m/z= 668.26 (C ₄₇ H ₃₂ N ₄ O =668.78) 1-338 m/z=591.23 (C ₄₂ H ₂₉ N ₃ O=591.70) 1-341 m/z= 641.22 (C ₄₄ H ₂₇ N ₃ O=641.72) 1-348 m/z= 655.20 (C ₄₄ H ₂₅ N ₅ O ₂ =655.70) 1-351 m/z= 584.30 (C ₃₇ H ₄ D ₁₈ N ₆ O=584.72) 1-352 m/z= 718.25 (C ₄₉ H ₃₀ N ₆ O=718.80) 1-354 m/z= 641.22 (C ₄₄ H ₂₇ N ₅ O=642.72) 1-364 m/z= 732.23 (C ₄₉ H ₂₈ N ₆ O ₂ =732.79) 1-369 m/z= 656.20 (C ₄₃ H ₂₄ N ₆ O ₂ =656.69) 1-371 m/z = 672.17 (C ₄₃ H ₂₄ N ₆ OS=672.76) 1-374 m/z= 823.24 (C ₅₆ H ₃₃ N ₅ OS=823.96) 1-379 m/z = 672.17 (C ₄₃ H ₂₄ N ₆ OS=672.76) 1-383 m/z= 682.25 (C ₄₆ H ₃₀ N ₆ O=682.77) 1-386 m/z= 682.25 (C ₄₆ H ₃₀ N ₆ O=682.77) 1-390 m/z= 758.28 (C ₅₂ H ₃₄ N ₆ O=758.87) 1-395 m/z= 731.24 (C ₄₉ H ₂₉ N ₇ O=731.80) 1-399 m/z = 883.31 (C ₆₁ H ₃₇ N ₇ O=883.99) 2-3 m/z= 560.23 (C ₄₂ H ₂₈ N ₂ =560.70) 2-4 m/z= 560.23 (C ₄₂ H ₂₈ N ₂ =560.70) 2-7 m/z= 636.26 (C ₄₈ H ₃₂ N ₂ =636.80) 2-31 m/z= 636.26 (C ₄₈ H ₃₂ N ₂ =636.80) 2-32 m/z= 636.26 (C ₄₈ H ₃₂ N ₂ =636.80) 2-42 m/z= 636.26 (C ₄₈ H ₃₂ N ₂ =636.78)

<Experimental Example 1>

1) Fabrication of an organic light emitting device

A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO-treated for 5 minutes using UV in a UV washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition equipment for organic deposition.

The hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and the hole transport layer NPB (N,N'-Di ( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. The emission layer was deposited by depositing 400 Å of compound 2-3 as a host, and the green phosphorescent dopant was deposited by doping Ir(ppy) ₃ 7% of the thickness of the emission layer deposition. After that, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq ₃ was deposited thereon as an electron transporting layer. Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. The organic light emitting device of Example 1 was manufactured.

The same method as in the manufacturing method of the organic light emitting device of Comparative Example 1, except for using the compounds shown in Tables 6 and 7 below instead of using Compound 2-3 as a host of the light emitting layer in the manufacturing process of the organic light emitting device of Comparative Example 1 The organic light emitting devices of Comparative Examples 2 to 13 and Examples 1 to 100 were additionally prepared.

On the other hand, all organic compounds required for manufacturing OLED devices were vacuum-sublimated and purified under 10 ^-8 to 10 ^-6 torr for each material, respectively, and used for OLED manufacturing.

2) Evaluation of organic light emitting devices

For the organic light emitting devices of Comparative Examples 1 to 13 and Examples 1 to 100 prepared as described above, electroluminescence (EL) characteristics were measured with M7000 of McScience, and the lifespan equipment manufactured by McScience based on the measurement results When the reference luminance was 6,000 cd/m ² through a measuring device (M6000), T ₉₀ was measured. Here, T ₉₀ denotes a lifetime (unit: h, time) that is 90% of the initial luminance.

The results of driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light emitting devices of Comparative Examples 1 to 13 and Examples 1 to 100 measured by the above measurement method are shown in Tables 6 and 7 below.

light emitting layer
compound drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 1 2-3 2.63 29.2 (0.233, 0.671) 45 Comparative Example 2 2-4 2.59 31.3 (0.231, 0.673) 48 Comparative Example 3 2-7 2.61 30.4 (0.237, 0.677) 44 Comparative Example 4 2-31 2.65 30.8 (0.234, 0.674) 43 Comparative Example 5 2-32 2.58 29.8 (0.231, 0.681) 44 Comparative Example 6 2-42 2.59 30.1 (0.233, 0.682) 43 Comparative Example 7 Ref. One 6.37 43.5 (0.234, 0.667) 135 Comparative Example 8 Ref. 2 6.40 43.0 (0.231, 0.683) 132 Comparative Example 9 Ref. 3 6.41 40.1 (0.230, 0.674) 125 Comparative Example 10 Ref. 4 6.44 40.9 (0.233, 0.675) 129 Comparative Example 11 Ref. 5 6.38 39.5 (0.235, 0.667) 119 Comparative Example 12 Ref. 6 6.05 45.7 (0.231, 0.682) 141 Comparative Example 13 Ref. 7 6.32 44.3 (0.234, 0.667) 137

[Comparative Example Compound]

light emitting layer
compound drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Example 1 1-1 4.44 53.0 (0.245, 0.670) 231 Example 2 1-7 4.47 52.7 (0.238, 0.670) 230 Example 3 1-13 4.45 51.9 (0.233, 0.669) 235 Example 4 1-18 4.49 52.5 (0.242, 0.673) 233 Example 5 1-20 4.46 52.5 (0.240, 0.666) 235 Example 6 1-21 4.48 52.6 (0.245, 0.662) 229 Example 7 1-24 4.53 52.5 (0.240, 0.670) 233 Example 8 1-30 4.58 52.6 (0.245, 0.662) 229 Example 9 1-31 4.47 53.5 (0.243, 0.666) 230 Example 10 1-38 4.49 52.8 (0.239, 0.679) 226 Example 11 1-41 4.53 53.5 (0.242, 0.670) 230 Example 12 1-45 4.43 53.1 (0.243, 0.666) 235 Example 13 1-51 4.45 53.5 (0.244, 0.661) 237 Example 14 1-54 4.33 54.0 (0.245, 0.670) 241 Example 15 1-60 4.44 54.7 (0.238, 0.670) 240 Example 16 1-61 4.45 54.9 (0.233, 0.669) 246 Example 17 1-63 4.39 54.5 (0.242, 0.673) 250 Example 18 1-65 4.36 54.5 (0.240, 0.666) 245 Example 19 1-75 4.38 54.6 (0.245, 0.662) 249 Example 20 1-77 4.45 54.7 (0.243, 0.671) 249 Example 21 1-81 4.39 54.5 (0.240, 0.670) 243 Example 22 1-87 4.47 54.4 (0.245, 0.675) 248 Example 23 1-90 4.49 54.2 (0.244, 0.671) 247 Example 24 1-91 4.37 54.4 (0.240, 0.671) 245 Example 25 1-93 4.48 54.9 (0.243, 0.669) 230 Example 26 1-101 4.40 56.4 (0.243, 0.671) 257 Example 27 1-102 4.38 56.8 (0.241, 0.672) 249 Example 28 1-108 4.37 56.0 (0.243, 0.672) 259 Example 29 1-114 4.27 55.8 (0.245, 0.665) 255 Example 30 1-119 4.36 56.1 (0.232, 0.672) 250 Example 31 1-122 4.30 55.3 (0.232, 0.681) 250 Example 32 1-125 4.39 56.1 (0.231, 0.684) 251 Example 33 1-132 4.40 55.6 (0.243, 0.674) 250 Example 34 1-133 4.33 54.7 (0.231, 0.681) 249 Example 35 1-136 4.31 54.9 (0.235, 0.674) 258 Example 36 1-143 4.42 55.8 (0.242, 0.675) 253 Example 37 1-146 4.39 55.1 (0.240, 0.672) 255 Example 38 1-149 4.43 55.9 (0.239, 0.678) 259 Example 39 1-152 4.33 56.2 (0.232, 0.675) 271 Example 40 1-155 4.25 57.7 (0.231, 0.680) 270 Example 41 1-162 4.26 58.5 (0.231, 0.679) 272 Example 42 1-164 4.21 58.0 (0.232, 0.678) 274 Example 43 1-167 4.27 57.9 (0.234, 0.665) 271 Example 44 1-176 4.20 56.6 (0.235, 0.668) 269 Example 45 1-179 4.31 58.2 (0.232, 0.666) 270 Example 46 1-183 4.29 57.6 (0.241, 0.671) 264 Example 47 1-188 4.30 58.0 (0.242, 0.667) 265 Example 48 1-192 4.40 56.3 (0.245, 0.661) 267 Example 49 1-195 4.29 58.1 (0.231, 0.664) 271 Example 50 1-200 4.31 57.9 (0.233, 0.671) 269 Example 51 1-201 4.30 57.5 (0.242, 0.672) 263 Example 52 1-203 4.32 56.9 (0.240, 0.676) 251 Example 53 1-209 4.37 57.4 (0.243, 0.676) 264 Example 54 1-215 4.20 56.8 (0.247, 0.685) 259 Example 55 1-220 4.31 56.0 (0.231, 0.674) 255 Example 56 1-223 4.27 56.3 (0.231, 0.684) 250 Example 57 1-226 4.35 57.1 (0.232, 0.685) 257 Example 58 1-234 4.37 55.7 (0.244, 0.673) 253 Example 59 1-237 4.30 55.3 (0.229, 0.682) 250 Example 60 1-240 4.28 55.1 (0.239, 0.673) 261 Example 61 1-244 4.39 56.5 (0.241, 0.672) 256 Example 62 1-247 4.32 56.3 (0.238, 0.675) 257 Example 63 1-249 4.38 56.0 (0.240, 0.681) 264 Example 64 1-251 4.26 58.2 (0.233, 0.678) 279 Example 65 1-254 4.16 58.5 (0.231, 0.675) 273 Example 66 1-263 4.25 59.6 (0.232, 0.678) 275 Example 67 1-268 4.19 59.1 (0.234, 0.678) 272 Example 68 1-270 4.27 58.9 (0.232, 0.668) 271 Example 69 1-273 4.15 57.8 (0.234, 0.675) 274 Example 70 1-280 4.29 59.0 (0.235, 0.667) 270 Example 71 1-284 4.25 58.7 (0.242, 0.672) 268 Example 72 1-289 4.27 58.5 (0.243, 0.666) 265 Example 73 1-293 4.36 57.9 (0.243, 0.671) 266 Example 74 1-296 4.23 59.3 (0.233, 0.665) 270 Example 75 1-298 4.29 58.0 (0.231, 0.672) 272 Example 76 1-301 4.65 61.0 (0.233, 0.678) 289 Example 77 1-304 4.51 51.6 (0.235, 0.669) 235 Example 78 1-310 4.49 51.8 (0.234, 0.669) 230 Example 79 1-316 4.51 52.0 (0.242, 0.671) 231 Example 80 1-320 4.47 51.4 (0.244, 0.661) 229 Example 81 1-324 4.50 51.7 (0.242, 0.664) 223 Example 82 1-327 4.59 51.9 (0.240, 0.672) 219 Example 83 1-330 4.58 52.5 (0.243, 0.661) 218 Example 84 1-335 4.52 52.8 (0.245, 0.665) 220 Example 85 1-338 4.52 52.9 (0.235, 0.675) 215 Example 86 1-341 4.55 52.8 (0.243, 0.671) 210 Example 87 1-348 4.49 53.0 (0.242, 0.665) 225 Example 88 1-351 4.62 62.4 (0.233, 0.678) 292 Example 89 1-352 4.39 53.8 (0.244, 0.666) 239 Example 90 1-354 4.49 54.0 (0.233, 0.669) 238 Example 91 1-364 4.50 54.2 (0.238, 0.670) 241 Example 92 1-369 4.41 53.9 (0.240, 0.665) 249 Example 93 1-371 4.38 53.8 (0.242, 0.662) 242 Example 94 1-374 4.37 53.6 (0.244, 0.670) 238 Example 95 1-379 4.46 53.7 (0.244, 0.673) 240 Example 96 1-383 4.41 53.9 (0.242, 0.666) 239 Example 97 1-386 4.52 53.8 (0.245, 0.671) 245 Example 98 1-390 4.50 54.0 (0.243, 0.670) 241 Example 99 1-395 4.43 54.1 (0.240, 0.661) 240 Example 100 1-399 4.49 53.9 (0.241, 0.664) 231

As can be seen from the results of Tables 6 and 7, the organic electroluminescent device using the light emitting layer material of the organic electroluminescent device of the present invention has a lower driving voltage and improved luminous efficiency as well as lifetime compared to Comparative Examples 1 to 13. significantly improved.

When the N-Het substituent of Formula 1 is a carbazole group as in the heterocyclic compounds of Comparative Examples 7 and 8, the T1 is 2.48, the driving voltage is high, and the LUMO is less spread, so the electron mobility is lowered, so that holes and electrons in the light emitting layer It was confirmed that the life and efficiency were lowered as the balance of

In the case of not having a substituent of N-Het of Formula 1 as in the heterocyclic compounds of Comparative Examples 9, 10 and 11, the LUMO is less spread and the electron mobility is lowered, and the balance of holes and electrons in the light emitting layer is broken, resulting in lifetime and efficiency It was confirmed that this was lowered.

When the core structure of Formula 1 is benzothienopyrimidine as in the heterocyclic compounds of Comparative Examples 12 and 13, Td is lower than that of benzofuranpyrimidine, and it is structurally destabilized, thereby reducing the lifespan.

On the other hand, when the heterocyclic compound represented by Chemical Formula 1 of the present application is used as a material of the light emitting layer, electrons become more abundant, heat stable, and the LUMO region expands so that the balance between holes and electrons is also suitable, so that the device is driven It was confirmed that the device lifespan characteristics could be improved by lowering the voltage, improving the light efficiency, and thermal stability of the compound.

<Experimental Example 2>

1) Fabrication of an organic light emitting device

A glass substrate coated with a thin film of ITO to a thickness of 1,500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic washing was performed with a solvent such as acetone, methanol, isopropyl alcohol, etc., dried, and UVO-treated for 5 minutes using UV in a UV washer. After transferring the substrate to a plasma cleaner (PT), plasma treatment was performed to remove the ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition equipment for organic deposition.

The hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) as a common layer on the ITO transparent electrode (anode) and the hole transport layer NPB (N,N'-Di ( 1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed.

A light emitting layer was deposited thereon by thermal vacuum deposition as follows. As the light emitting layer as a host, as described in Table 8 below, the compound of Ref. 1 and compound 2-32 were pre-mixed and then 400 Å deposited in one park, and the green phosphorescent dopant was Ir(ppy) ₃ as the light emitting layer Deposited by doping 7% of the deposition thickness. Thereafter, 60 Å of BCP was deposited as a hole blocking layer, and 200 Å of Alq3 was deposited thereon as an electron transporting layer. Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode. The organic light emitting device of Example 14 was manufactured.

Comparative Example 14, except that, instead of premixing and using the compound of Ref. 1 and Compound 2-32 as a host of the light emitting layer in the manufacturing process of the organic light emitting device of Comparative Example 14, the compounds shown in Table 8 were premixed and used Organic light emitting devices of Comparative Examples 15 to 19 and Examples 101 to 139 were additionally prepared in the same manner as in the method of manufacturing the organic light emitting device of

On the other hand, all organic compounds required for manufacturing OLED devices were vacuum-sublimated and purified under 10 ^-8 to 10 ^-6 torr for each material, respectively, and used for OLED manufacturing.

2) Evaluation of organic light emitting devices

For the organic light emitting devices of Comparative Examples 14 to 19 and Examples 101 to 139 prepared as described above, electroluminescence (EL) characteristics were measured with M7000 of McScience, and the lifespan equipment manufactured by McScience based on the measurement results When the reference luminance was 6,000 cd/m ² through a measuring device (M6000), T ₉₀ was measured.

The results of driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the organic light emitting diodes of Comparative Examples 1 to 13 and Example 100 measured by the above measurement method are shown in Table 8 below.

light emitting layer
compound ratio drive voltage
(V) efficiency
(cd/A) color coordinates
(x, y) life span
(T ₉₀ ) Comparative Example 14 Ref. 1: 2-32 1: 2 4.70 67.4 (0.242, 0.710) 438 Comparative Example 15 Ref. 1: 2-32 1:1 4.65 65.9 (0.242, 0.724) 427 Comparative Example 16 Ref. 1: 2-32 2:1 4.61 65.4 (0.241, 0.711) 419 Comparative Example 17 Ref. 6: 2-32 1: 2 4.64 68.8 (0.241, 0.722) 442 Comparative Example 18 Ref. 6: 2-32 1:1 4.60 66.5 (0.252, 0.714) 433 Comparative Example 19 Ref. 6: 2-32 2:1 4.53 66.3 (0.231, 0.712) 431 Example 101 1-1: 2-31 1: 2 4.21 76.8 (0.231, 0.710) 526 Example 102 1-1: 2-31 1:1 4.17 75.3 (0.233, 0.712) 491 Example 103 1-1: 2-31 2:1 4.09 70.2 (0.253, 0.711) 469 Example 104 1-51 : 2-42 1: 2 4.17 77.1 (0.242, 0.714) 531 Example 105 1-51 : 2-42 1:1 4.01 76.0 (0.231, 0.713) 497 Example 106 1-51 : 2-42 2:1 3.90 70.6 (0.251, 0.713) 471 Example 107 1-101: 2-32 1: 2 4.24 78.3 (0.212, 0.714) 552 Example 108 1-101: 2-32 1:1 4.18 77.2 (0.221, 0.721) 505 Example 109 1-101: 2-32 2:1 3.99 71.8 (0.231, 0.711) 496 Example 110 1-149: 2-31 1: 2 4.20 77.3 (0.242, 0.724) 547 Example 111 1-149: 2-31 1:1 4.11 76.4 (0.232, 0.711) 501 Example 112 1-149: 2-31 2:1 3.85 70.2 (0.233, 0.720) 482 Example 113 1-152 : 2-42 1: 2 4.23 79.3 (0.241, 0.714) 567 Example 114 1-152 : 2-42 1:1 4.20 77.9 (0.243, 0.715) 521 Example 115 1-152 : 2-42 2:1 4.11 72.8 (0.243, 0.712) 495 Example 116 1-167: 2-3 1:8 4.37 69.5 (0.243, 0.713) 481 Example 117 1-167: 2-3 1: 5 4.35 70.3 (0.233, 0.714) 499 Example 118 1-167: 2-3 1: 2 4.25 79.1 (0.252, 0.715) 555 Example 119 1-167: 2-3 1:1 4.21 77.5 (0.232, 0.711) 518 Example 120 1-167: 2-3 2:1 4.17 72.7 (0.234, 0.712) 505 Example 121 1-167: 2-3 5 : 1 4.40 70.0 (0.231, 0.715) 495 Example 122 1-167: 2-3 8:1 4.52 69.1 (0.252, 0.711) 482 Example 123 1-201 : 2-31 1: 2 4.20 79.9 (0.232, 0.710) 570 Example 124 1-201 : 2-31 1:1 4.17 78.3 (0.230, 0.711) 526 Example 125 1-201 : 2-31 2:1 3.98 73.3 (0.233, 0.713) 513 Example 126 1-226 : 2-42 1: 2 4.20 80.1 (0.244, 0.710) 574 Example 127 1-226 : 2-42 1:1 4.15 79.0 (0.231, 0.711) 531 Example 128 1-226 : 2-42 2:1 4.07 73.8 (0.233, 0.714) 520 Example 129 1-251 : 2-7 1: 2 4.12 81.5 (0.251, 0.725) 581 Example 130 1-251 : 2-7 1:1 3.95 79.4 (0.240, 0.710) 535 Example 131 1-251 : 2-7 2:1 3.81 74.1 (0.242, 0.717) 529 Example 132 1-301: 2-4 1: 3 4.41 75.5 (0.244, 0.710) 459 Example 133 1-301: 2-4 1: 2 4.20 85.2 (0.231, 0.710) 592 Example 134 1-301: 2-4 1:1 3.98 80.3 (0.233, 0.712) 482 Example 135 1-301: 2-4 2:1 3.97 78.1 (0.253, 0.711) 460 Example 136 1-301: 2-4 3 : 1 4.50 74.2 (0.244, 0.710) 455 Example 137 1-354 : 2-7 1: 2 4.23 75.7 (0.252, 0.716) 504 Example 138 1-354 : 2-7 1:1 4.00 74.9 (0.234, 0.713) 479 Example 139 1-354 : 2-7 2:1 3.92 71.8 (0.232, 0.711) 461

Looking at the results of Tables 7 and 8, when the heterocyclic compound of Formula 1 and the compound of Formula 2 are included at the same time, better efficiency and lifespan effect are exhibited. This result can be expected to occur when both compounds are included at the same time exciplex (exciplex) phenomenon

The exciplex phenomenon is a phenomenon in which energy having a size of a HOMO level of a donor (p-host) and a LUMO level of an acceptor (n-host) is emitted through electron exchange between two molecules. When an exciplex phenomenon occurs between two molecules, Reverse Intersystem Crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts of the emission layer, holes are injected into the p-host and electrons are transferred to the n- Since it is injected into the host, the driving voltage can be lowered, thereby helping to improve the lifespan.

From the above results, when the compound of Formula 2 of the present application serving as a donor and the heterocyclic compound of Chemical Formula 1 of the present application serving as an acceptor are used as a light emitting layer host, excellent device properties It could be confirmed that the

100: substrate
200: positive electrode
300: organic layer
301: hole injection layer
302: hole transport layer
303: light emitting layer
304: hole blocking layer
305: electron transport layer
306: electron injection layer
400: cathode

Claims (13)

A heterocyclic compound represented by the following formula (1):
[Formula 1]

In Formula 1,
L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a is an integer of 0 to 2, and when a is 2, L1 in parentheses are the same as or different from each other,
Ar1 is a substituted or unsubstituted C6-C60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
N-Het is substituted or unsubstituted,

It is a monocyclic or polycyclic heterocyclic group having 2 to 60 carbon atoms including one or more bonds,
R1 and Rp are hydrogen; heavy hydrogen; cyano group; or a substituted or unsubstituted C 1 to C 60 alkyl group, p is an integer from 0 to 3, and when p is 2 or more, Rp in parentheses are the same as or different from each other. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, the definitions of L1, Ar1, R1, N-Het and a are the same as in Formula 1,
R2 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; or a substituted or unsubstituted C 1 to C 60 alkyl group. The heterocyclic compound according to claim 1, wherein N-Het is a group represented by the following formula (A):
[Formula A]

In the formula A,
X1 is CR11 or N, X2 is CR12 or N, X3 is CR13 or N, X4 is CR14 or N, X5 is CR15 or N, wherein X1 to X5 at least one of them is N;
R11 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C 3 to C 60 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; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiR101R102R103; -P(=O)R104R105; and -NR106R107, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or a hetero ring, wherein R101 to R107 are the same as or different from each other, and each independently Hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,

is a site connected to Formula 1 above. The method according to claim 1, wherein Chemical Formula 1 is a heterocyclic compound represented by any one of the following Chemical Formulas 1-1-1 to 1-4-1:
[Formula 1-1-1]

[Formula 1-2-1]

[Formula 1-3-1]

[Formula 1-4-1]

In Formulas 1-1-1 to 1-4-1, the definitions of L1, R1, Rp, N-Het, a and p are the same as in Formula 1,
Y1 and Y2 are each independently O; S; CRaRb or NRc, wherein Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 60 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, wherein Rc is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,
R16 to R23 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; cyano group; or a substituted or unsubstituted C 1 to C 60 alkyl group; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, b is an integer from 0 to 3, c to h are each independently an integer from 0 to 4, i is an integer from 0 to 6, b to i When each is 2 or more, the substituents in parentheses are the same as or different from each other. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

A first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is a heterocyclic compound according to any one of claims 1 to 5. An organic light emitting device comprising a. The organic light emitting device of claim 6 , wherein the organic material layer includes one or more light emitting layers, and the light emitting layer includes the heterocyclic compound. The organic light emitting diode of claim 7 , wherein the light emitting layer may include two or more host materials, and at least one of the host materials includes the heterocyclic compound as a host material of the light emitting material. The method according to claim 6, wherein the organic light emitting device further comprises 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, a hole auxiliary layer, and a hole blocking layer phosphorus organic light emitting device. The organic light-emitting device according to claim 6, wherein the organic material layer further comprises a heterocyclic compound represented by Formula 1 as a first compound, and further comprising a heterocyclic compound represented by Formula 2 as a second compound:
[Formula 2]

In Formula 2,
R24 and R25 are the same as or different from each other, and each independently -SiR101R102R103; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
R26 and R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C 3 to C 60 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; a substituted or unsubstituted C 2 to C 60 heteroaryl group; -SiR101R102R103; -P(=O)R104R105; and -NR106R107, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or a hetero ring, wherein R101 to R107 are the same as or different from each other, and each independently Hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C 6 to C 60 aryl group; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
r and s are integers from 0 to 7, and when r is 2 or more, R26 is the same as or different from each other, and when s is 2 or more, R27 is the same as or different from each other. The organic light emitting diode of claim 10, wherein Chemical Formula 2 is represented by any one of the following compounds:

A composition for an organic material layer of an organic light emitting device comprising the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 according to claim 1 :
[Formula 2]

In Formula 2,
R24 and R25 are the same as or different from each other, and each independently -SiR101R102R103; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
R26 and R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; cyano group; a substituted or unsubstituted C 1 to C 60 alkyl group; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted C 1 to C 20 alkoxy group; a substituted or unsubstituted C 3 to C 60 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; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -SiR101R102R103; -P(=O)R104R105; and -NR106R107, or two or more groups adjacent to each other combine with each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or a hetero ring, wherein R101 to R107 are the same as or different from each other, and each independently Hydrogen; heavy hydrogen; halogen group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
r and s are integers from 0 to 7, and when r is 2 or more, R26 is the same as or different from each other, and when s is 2 or more, R27 is the same as or different from each other. 13. The method of claim 12,
In the composition, the weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 2 is 1:10 to 10:1. The composition for an organic material layer of an organic light emitting device.

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