KR20190033901A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound represented by chemical formula 1 and an organic light emitting device comprising the same. According to the present invention, the heterocyclic compound represented by the chemical formula 1 may be used in an organic material layer of an organic light emitting device, thereby lowering the driving voltage of the device and improving the light efficiency of the device. Furthermore, due to thermal stability of the compound, lifetime characteristics of the device may be improved.

Description

TECHNICAL FIELD [0001] The present invention relates to a heterocyclic compound and an organic light emitting device including the heterocyclic compound. [0002]

TECHNICAL FIELD The present invention relates to heterocyclic compounds and organic light emitting devices comprising the same.

An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high 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 couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.

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

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

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

The present invention provides a novel heterocyclic compound and an organic light emitting device including the same.

In one embodiment of the present application, there is provided a heterocyclic compound represented by the following general formula (1).

[Chemical Formula 1]

In Formula 1,

R ₂ to R ₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group Or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,

R _a is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Ar ₁ is represented by - (L1) p- (Z1) q,

Ar ₂ is represented by - (L2) r- (Z2) s,

L1 and L2 are the same or different from each other and each independently represents a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Z1 and Z2 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group And,

Wherein R, R 'and R "are the same or different from each other and each independently represents hydrogen, deuterium, -CN, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, Or an unsubstituted heteroaryl group,

p and r are integers of 1 to 4,

q and s are integers of 1 to 3,

n is an integer of 0 to 4;

In addition, in one embodiment of the present application, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a heterocyclic compound according to one embodiment of the present application. A light emitting device is provided.

The compound described in this specification can be used as an organic layer material of an organic light emitting device. The compound can act as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like in an organic light emitting device. In particular, the compound can be used as an electron transporting layer material, a hole blocking layer material, or a charge generating layer material of an organic light emitting device.

Specifically, when the compound represented by Formula 1 is used for an organic material layer, the driving voltage of the device can be lowered, the light efficiency can be improved, and the lifetime characteristics of the device can be improved by the thermal stability of the compound.

FIGS. 1 to 4 schematically show a laminated structure of an organic light emitting diode according to one embodiment of the present application.

The present application will be described in detail below.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

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

In the present specification, the alkyl group includes a straight chain or a branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically 1 to 20. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, An n-pentyl group, a tert-butyl group, a tert-butyl group, a 3-methylbutyl group, a 3-methylbutyl group, a 2-ethylbutyl group, a heptyl group, 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 chain or a 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, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.

In the present specification, the alkynyl group includes a straight chain or a 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 linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the cycloalkyl group includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted by other substituents. Herein, the term "polycyclic" means a group in which a cycloalkyl group is directly connected to another ring group or condensed therewith. Here, the other ring group may be a cycloalkyl group, but may be another ring group such as a heterocycloalkyl group, an aryl group, a heteroaryl group and the like. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more particularly 5 to 20. Specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, , 3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but are not limited thereto.

In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic ring means a group in which the heterocycloalkyl group is directly connected to another ring group or condensed. Here, the other ring group may be a heterocycloalkyl group, but may be another ring group such as a cycloalkyl group, an aryl group, a heteroaryl group and the like. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

In the present specification, the aryl group includes monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be further substituted by other substituents. Herein, a polycyclic ring means a group in which an aryl group is directly connected to another ring group or condensed with another ring group. Here, the other ring group may be an aryl group, but may be another kind 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 triphenyl group, a naphthyl group, an anthryl group, a klychenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, An acenaphthyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, a condensed ring group thereof, a thiophenecarbonyl group, , But are not limited thereto.

In this specification, the silyl group is a substituent including Si and a direct connection as the Si atom radical, R is represented by -SiR _{104 105} R _106, R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And 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 and a phenylsilyl group. But is not limited thereto.

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

,

,

,

,

,

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

,

,

,

,

,

And the like, but the present invention is not limited thereto.

In the present specification, the heteroaryl group includes S, O, Se, N or Si as a hetero atom and includes monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be further substituted by other substituents. Herein, the polycyclic ring means a group in which the heteroaryl group is directly connected to another ring group or condensed therewith. Here, the other ring group may be a heteroaryl group, but may be another ring group such as a cycloalkyl group, a heterocycloalkyl group, an aryl group and the like. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, 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, A thiazolyl group, a thiazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a paranyl group, a thiopyranyl group, a diazinyl group, , A thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinolizolyl group, a naphthyridyl group, An imidazopyridinyl group, a diazanaphthalenyl group, a triazinediyl group, an indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophenyl group, a benzothiophenyl group , A dibenzothiophene group, a dibenzofuran group, a carbazolyl group, a benzocarbazolyl group, (Dibenzosilyl), dihydrophenazinyl, phenoxazinyl, phenanthridyl, imidazopyridinyl, thienyl, indolo [3,3-d] pyrimidinyl, 2,3-a] carbazolyl group, indolo [2,3-b] carbazolyl group, indolinyl group, 10,11-dihydrodibenzo [b, f] azepine group, 9,10-dihydro A phenanthrolinyl group, a phenanthrazinyl group, a phenothiatriazinyl group, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo [c] [1,2,5] thiadiazolyl group, 1,5-c] quinazolinyl group, pyrido [l, 2-b] indazolyl group, pyrido [l, 2- a] imidazo [1,2-e] indolinyl group, and 5,11-dihydroindeno [1,2-b] carbazolyl group.

In the present specification, the amine group is a monoalkylamine group; Monoarylamine groups; A monoheteroarylamine group; -NH ₂ ; A dialkylamine group; A diarylamine group; A diheteroarylamine group; Alkylarylamine groups; Alkylheteroarylamine groups; And an arylheteroarylamine 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 diphenylamine group, an anthracenylamine group, A phenylphenylamine group, a diphenylamine group, a methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, Naphthylamine amine group, phenylnaphthylamine amine group, phenylnaphthylamine amine group, biphenyltriphenylenylamine group, and the like.

In the present specification, an arylene group means a group having two bonding positions in an aryl group, that is, a divalent group. The description of the aryl group described above can be applied except that each of these is 2 groups. Further, the heteroarylene group means that the heteroaryl group has two bonding positions, i.e., divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

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

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

As used herein, the term "substituted or unsubstituted" means straight or branched chain alkyl of C1 to C60; C2 to C60 straight or branched chain alkenyl; Straight or branched chain alkynyl of C2 to C60; C3 to C60 monocyclic or polycyclic cycloalkyl; A C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; Wherein R is selected from the group consisting of C1 to C20 alkylamines, C6 to C60 mono- or polycyclic arylamines, and C2 to C60 mono- or polycyclic heteroarylamines. Is substituted or unsubstituted with at least one substituent, or at least two substituents selected from the substituents exemplified above are substituted or unsubstituted with a substituted substituent.

In one embodiment of the present application, the compound represented by Formula 1 is provided.

The above formula (1) has a structure in which a quinoline group is condensed in an indole group. When the above formula (1) has an indole group, it has no sp2 unpaired electron pair in its structure and has a sp3 unshared electron pair. Therefore, the hole transporting property is particularly superior to the case of having benzothiophene or benzofuran having sp2 noncovalent bond. This may affect the formation of an exciton in the light emitting layer when used as an organic material layer of the organic light emitting device, thereby increasing the lifetime of the device.

In one embodiment of the present application, R ₂ to R ₅ in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group Or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring.

In another embodiment, R ₂ to R ₅ in Formula 1 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted C1 to C60 aryl group; And a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.

In another embodiment, R ₂ to R ₅ in Formula 1 are the same or different and each independently hydrogen or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C2 to C60 aromatic hydrocarbon A ring can be formed.

In another embodiment, R ₂ to R ₅ in Formula 1 are the same or different and each independently hydrogen or two or more adjacent groups may be bonded to each other to form a C 2 to C 40 aromatic hydrocarbon ring have.

In another embodiment, R ₂ to R ₅ in Formula 1 are the same or different and each independently hydrogen or two or more groups adjacent to each other may be bonded to each other to form a benzene ring.

In one embodiment of the present application, R ₂ and R ₃ of R ₂ to R ₅ in Formula 1 may be bonded to each other to form a benzene ring, and the remainder may be hydrogen.

In one embodiment of the present application, R ₃ and R ₄ of R ₂ to R ₅ in Formula 1 may be bonded to each other to form a benzene ring, and the remainder may be hydrogen.

In one embodiment of the present application, R ₄ and R ₅ of R ₂ to R ₅ of Formula 1 may be bonded to each other to form a benzene ring, and the remainder may be hydrogen.

In one embodiment of the present application, R _a in Formula 1 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In another embodiment, R _a in Formula 1 is hydrogen; A substituted or unsubstituted C6 to C60 aryl group; Or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another embodiment, R _a in Formula 1 is hydrogen; A C6 to C40 aryl group; Or a C2 to C40 heteroaryl group.

In another exemplary embodiment, R _a in the formula (I) may be hydrogen.

Up there to an exemplary embodiment of the present application, wherein Ar ₁ is - can be represented by (L2) r- (Z2) s - (L1) p- (Z1) it is represented by q, wherein Ar ₂ is.

Ar ₁ of formula ( ₁₎ And Ar ₂ are substituted with the respective substituents, the thermal stability is superior to that of the single substitution, and the introduction of substituents structurally controlling the hole transporting property of the indole structure can be introduced more variously than when the single substitution is performed, It may be better to control the characteristics of the structure.

In one embodiment of the present application, L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In another embodiment, L 1 and L 2 are the same or different and each independently represents a substituted or unsubstituted C 6 to C 60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In another embodiment, L 1 and L 2 are the same or different from each other, and are each independently an C6 to C40 arylene group; Or a C2 to C40 heteroarylene group.

In another embodiment, L 1 and L 2 are the same or different from each other, and are each independently an C6 to C40 arylene group; Or a C2 to C40 heteroarylene group.

In another embodiment, L 1 and L 2 are the same or different from each other, and each independently represents a phenylene group; Biphenylene group; A naphthalene group; Phenanthrenylene group; Triphenylenylene group; Fluoranthenylene group; Pyrenylene group; A divalent pyridine group; A divalent pyrimidine group; Or a bivalent triazine group.

In one embodiment of the present application, L 1 is a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In another embodiment, L < 1 > is a substituted or unsubstituted C6 to C40 arylene group; Or a substituted or unsubstituted C2 to C40 heteroarylene group.

In another embodiment, L < 1 > is a C6 to C40 arylene group; Or a C2 to C40 heteroarylene group.

In another embodiment, L < 1 > is a phenylene group; Biphenylene group; A naphthalene group; Phenanthrenylene group; A divalent pyridine group; A divalent pyrimidine group; Or a bivalent triazine group.

In one embodiment of the present application, L2 is a substituted or unsubstituted C6 to C60 arylene group; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

In another embodiment, L2 is a substituted or unsubstituted C6 to C40 arylene group; Or a substituted or unsubstituted C2 to C40 heteroarylene group.

In another embodiment, L2 is a C6 to C40 arylene group; Or a C2 to C40 heteroarylene group.

In another embodiment, L2 is a phenylene group; Biphenylene group; A naphthalene group; Phenanthrenylene group; Triphenylenylene group; Fluoranthenylene group; Pyrenylene group; A divalent pyridine group; A divalent pyrimidine group; Or a bivalent triazine group.

In one embodiment of the present application, Z1 and Z2 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R "; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group .

In another embodiment, Z1 and Z2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; Or P (= O) RR '.

In another embodiment, Z1 and Z2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted C6 to C60 aryl group; A substituted or unsubstituted C2 to C60 heteroaryl group; Or P (= O) RR '.

In another embodiment, Z1 and Z2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted C6 to C40 aryl group; A substituted or unsubstituted C2 to C40 heteroaryl group; Or P (= O) RR '.

In another embodiment, Z1 and Z2 are the same or different from each other, and each independently hydrogen; A C6 to C40 aryl group which is substituted or unsubstituted with at least one substituent selected from the group consisting of C6 to C40 aryl groups, C2 to C40 heteroaryl groups, C1 to C40 alkyl groups and -CN; A C2 to C40 heteroaryl group substituted or unsubstituted with an aryl group of C6 to C40; Or P (= O) RR ', wherein the substituent is again a C1 to C40 alkyl group; Or an aryl group of C6 to C40.

In another embodiment, Z1 and Z2 are the same or different from each other, and each independently hydrogen; P (= O) RR '; A phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a 9,9'-dimethylfluorene group, -CN, a triphenylene group, a phenanthrene group, a phenyl group, a dibenzofurane group and a dibenzothiophene group; A phenyl group substituted or unsubstituted with a carbazole group substituted or unsubstituted with a phenyl group; Biphenyl group; Triphenylene group; A fluorene group substituted or unsubstituted with a methyl group; Phenanthrene; A spirobifluorene group; A pyridine group; Carbazole group; A dibenzofurane group; A dibenzothiophene group; Or a phenanthroline group substituted or unsubstituted with a phenyl group.

In one embodiment of the present application, Z1 is hydrogen; P (= O) RR '; A phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a carbazole group substituted with a phenyl group, a dibenzofurane group and a dibenzothiophene group; Biphenyl group; A spirobifluorene group; A fluorene group substituted or unsubstituted with a methyl group; A pyridine group; A dibenzofurane group; A dibenzothiophene group; Or a phenanthroline group substituted or unsubstituted with a phenyl group.

In one embodiment of the present application, Z2 is selected from the group consisting of hydrogen; P (= O) RR '; A phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a phenyl group, a phenanthrene group, a triphenylene group, -CN, a 9,9'-dimethylfluorene group, a carbazole group and a dibenzofurane group; Biphenyl group; Triphenylene group; A fluorene group substituted or unsubstituted with a methyl group; Phenanthrene; A pyridine group; Carbazole group; Or a dibenzofurane group.

A substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkyl group, Or an unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

In another embodiment, R, R 'and R "may be the same or different and each independently a substituted or unsubstituted aryl group.

In another embodiment, R, R 'and R "may be the same or different and each independently a substituted or unsubstituted C6 to C60 aryl group.

In another embodiment, R, R 'and R "may be the same or different and each independently a substituted or unsubstituted C6 to C40 aryl group.

In another embodiment, R, R 'and R "may be the same or different from each other, and each independently may be a C6 to C40 aryl group.

In another embodiment, R, R 'and R "may be the same or different from each other, and each may be a phenyl group.

In one embodiment of the present application, the present invention provides a heterocyclic compound represented by any one of the following formulas (2) to (9).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above Chemical Formulas 2 to 9,

R _a, Ar ₁ , Ar ₂ , R ₂ to R ₅ and n are the same as defined in the above formula (1).

In one embodiment of the present application, the present invention provides a heterocyclic compound wherein the above-mentioned formula (1) is represented by any one of the following compounds.

A compound according to one embodiment of the present application may be prepared according to the following general formula (1).

In the general formula (1), R ₁₀ or R ₁₁ is the same as defined for Ar ₁ or Ar ₂ in the general formula (1).

Also, by introducing various substituents into the structures of the above formulas (1) to (9), it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used for a hole injecting layer material, a hole transporting material, a light emitting layer material, an electron transporting layer material, and a charge generating layer material used in manufacturing an organic light emitting device into the core structure, Can be synthesized.

In addition, by introducing various substituents into the structures of the formulas (1) to (9), it is possible to finely control the energy band gap and improve the characteristics at the interface between the organic materials, .

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

The heterocyclic compound according to one embodiment of the present application can be prepared by a multistage chemical reaction. Some intermediate compounds may be prepared first, and compounds of formula (1) may be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application can be prepared on the basis of the following production example.

In addition, in one embodiment of the present application, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a heterocyclic compound according to Formula 1, to provide.

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

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

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

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

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

The details of the heterocyclic compound represented by the formula (1) are the same as described above.

The organic light emitting device of the present invention can be manufactured by a conventional method and materials for manufacturing an organic light emitting device, except that the above-described heterocyclic compound is used to form one or more organic compound layers.

The heterocyclic compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of 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.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

In the organic light emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound.

In the organic light emitting device of the present invention, the organic material layer may include an electron transporting layer, and the electron transporting layer may include the heterocyclic compound.

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

In another organic light emitting device, the organic layer may include a hole blocking layer, and the hole blocking layer may include the heterocyclic compound.

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

The organic light emitting device of the present invention includes a light emitting layer, a hole injecting layer, and a hole transporting layer. An electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

FIGS. 1 to 3 illustrate the stacking process of the electrode and the organic layer of the organic light emitting diode according to one 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 the organic light emitting device known in the art can be applied to the present application.

1, an organic light emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown. However, the present invention is not limited to such a structure, and 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 as shown in FIG.

FIG. 3 illustrates the case where the organic material layer is a multilayer. 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 the light emitting layer may be omitted, and other necessary functional layers may be further added.

The organic material layer containing the above chemical formulas (1) to (9) may further contain other materials as required.

Further, the organic light emitting element according to one embodiment of the present application includes two or more stacks each provided between an anode, a cathode, and an anode and a cathode, each of the two or more stacks includes a light emitting layer, And the charge generation layer comprises a heterocyclic compound represented by the above formula (1).

The organic light emitting device according to one embodiment of the present application includes a positive electrode, a first stack provided on the positive electrode and including a first light emitting layer, a charge generation layer provided on the first stack, A second stack including a second light emitting layer, and a cathode provided on the second stack. At this time, the charge generation layer may include a heterocyclic compound represented by the general formula (1). The first and second stacks may further include at least one of the hole injection layer, the hole transport layer, the hole blocking layer, the electron transport layer, and the electron injection layer described above independently.

The charge generation layer may be an N-type charge generation layer, and the charge generation layer may further include a dopant known in the art in addition to the heterocyclic compound represented by Formula (1).

An organic light emitting device having a two-stack tandem structure as an organic light emitting device according to one embodiment of the present application is schematically shown in Fig.

At this time, the first electron blocking layer, the first hole blocking layer, the second hole blocking layer, and the like described in FIG. 4 may be omitted in some cases.

In the organic light emitting device according to one embodiment of the present application, materials other than the compounds represented by Chemical Formulas 1 to 9 are illustrated below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, , ≪ / RTI >

As the cathode material, materials having a relatively large work function can be used, and a transparent conductive oxide, a metal, or a conductive polymer can be used. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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

As the hole injecting material, a known hole injecting material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a compound described in Advanced Material, 6, p. 677 (1994) Star burst type amine derivatives such as tris (4-carbamoyl-9-phenyl) amine (TCTA), 4,4 ', 4 "-tri [phenyl (m- tolyl) amino] triphenylamine MTDAPA), polyaniline / dodecylbenzenesulfonic acid (poly (vinylidene fluoride)) or poly (vinylidene fluoride), which is a soluble conductive polymer, such as 1,3,5-tris [4- (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate), polyaniline / camphor sulfonic acid or polyaniline / Poly (4-styrene-sulfonate) and the like can be used.

As the hole transporting material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or a high molecular weight material may be used.

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

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

As the light emitting material, red, green or blue light emitting materials may be used, and if necessary, two or more light emitting materials may be mixed and used. At this time, two or more luminescent materials may be used as a separate source of vapor deposition, or may be premixed and deposited as a single source. Further, a fluorescent material may be used as a light emitting material, but it may be used as a phosphorescent material. As the light emitting material, a material which emits light by coupling holes and electrons respectively injected from the anode and the cathode may be used. However, materials in which both the host material and the dopant material participate in light emission may also be used.

When a host of a light emitting material is mixed and used, a host of the same series may be used in combination, or a host of another series may be mixed and used. For example, two or more kinds of materials of an n-type host material or a p-type host material may be selected and used as a host material of the light emitting layer.

The organic light emitting device according to one embodiment of the present application may be a top emission type, a back emission type, or a both-sided emission type, depending on the material used.

The heterocyclic compound according to one embodiment of the present application may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.

Hereinafter, the present invention will be described in more detail by way of examples, but these are for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

< Manufacturing example >

< Manufacturing example  1> Preparation of compound 1

1) Preparation of Compound 1-1

(1H-indol-2-yl) boronic acid (100 g, 0.621 mol) and 2-bromoaniline (96 g, 0.558 mol) Pd (PPh ₃ ) ₄ (35.8 g, 0.031 mol) and NaHCO ₃ (156.5 g, 1.863 mol) were added to toluene (Toluene), EtOH and H ₂ O Lt; 0 &gt; C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 1-1 (94 g, 72%) in liquid form.

2) Preparation of Compound 1-2

Compound 1-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol) are dissolved in 1200 mL of MC. 4-Bromobenzoyl chloride (108.9 g, 0.496 mol) is dissolved in 300 mL of MC, and then slowly added dropwise to the mixture at 0 ° C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a liquid type compound 1-2 (150 g, 85%).

3) Preparation of compound 1-3

Compound 1-2 (150 g, 0.383 mol) is dissolved in nitrobenzene (1500 mL), and then POCl ₃ (35 mL, 0.383 mol) is slowly added dropwise. And reacted at 140 캜 for 15 hours. After completion of reaction, add NaHCO ₃ dissolved in distilled water to the reaction solution slowly and stir. The resulting solids are filtered and collected. The collected solid was recrystallized from MC and MeOH to give solid compound 1-3 (68 g, 48%).

4) Preparation of compounds 1-4

(9.9 g, 0.039 mol), KOAc (7.6 g, 0.078 mol), PdCl ₂ (dppf) (0.07 mol), Compound (1-3) (10 g, 0.026 mol), bis (pinacolato diboron) 0.9 g, 0.0013 mol) is dissolved in 1,4-dioxane (200 mL) and reacted at 90 ° C. for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 1-4 (10 g, 91%).

5) Preparation of compound 1-5

Compound 1 (10 g, 0.023 mol), 2-bromo-4,6-diphenyl-1,3,5-triazine (PPh ₃ ) ₄ (1.3 g, 0.0011 mol) and K ₂ CO ₃ (9.5 g, 0.023 mol) were dissolved in toluene (toluene), EtOH and H ₂ O , 0.069 mol), and the mixture is stirred at 100 DEG C for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 1-5 (9 g, 74%).

6) Preparation of compound 1

Compound 1 (9 g, 0.017 mol) and bromobenzene (3.2 g, 0.021 mol) were dissolved in toluene (100 mL) and Pd ₂ (dba) ₃ (1.5 g, 0.0017 mol) Tri-tert-butylphosphine (0.6 g, 0.034 mol) and sodium tert-butoxide (4.9 g, 0.051 mol) were added and stirred at 100 ° C for 15 hours. After completion of the reaction, the solution was cooled to room temperature, and the resulting solid was filtered to obtain Compound 1 (7.5 g, 73%) after drying.

Except that 2-bromo-4,6-diphenyl-1,3,5-triazine was used in place of 2-bromo-4,6-diphenyl- A, the target compound was synthesized.

In the same manner as in Preparation Example 1, except that the intermediate B shown in the following Table 2 was used in place of 4-bromobenzoyl chloride and 2-bromo-4,6-diphenyl-1,3,5-triazine (2 -bromo-4,6-diphenyl-1,3,5-triazine) was used instead of the intermediate C in Table 2, the target compound was synthesized.

Except that Intermediate D shown in the following Table 3 was used in place of 2-bromoaniline in Preparation Example 1, and 2-bromo-4,6-diphenyl-1,3,5-triazine was used instead of 2- -4,6-diphenyl-1,3,5-triazine) was used instead of Intermediate E in Table 3, the target compound was synthesized.

< Manufacturing example  2> Preparation of Compound 135

1) Preparation of compound 135-1

(1H-indol-2-yl) boronic acid (100 g, 0.621 mol) and 2-bromoaniline (96 g, 0.558 mol) Pd (PPh ₃ ) ₄ (35.8 g, 0.031 mol) and NaHCO ₃ (156.5 g, 1.863 mol) were added to toluene (Toluene), EtOH and H ₂ O Lt; 0 &gt; C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator to obtain a liquid form compound 135-1 (94 g, 72%).

2) Preparation of compound 135-2

Compound 135-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol) are dissolved in 1200 mL of MC. Benzoyl chloride (69.7 g, 0.496 mol) is dissolved in 300 mL of MC and then slowly added dropwise to the mixture at 0 ° C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed by a rotary evaporator to obtain a liquid form compound 135-2 (112 g, 80%).

3) Preparation of compound 135-3

Compound 135-2 (112 g, 0.358 mol) is dissolved in 1000 mL of Nitrobenzene, and then POCl ₃ (33 mL, 0.358 mol) is slowly added dropwise. And reacted at 140 캜 for 15 hours. After completion of reaction, add NaHCO ₃ dissolved in distilled water to the reaction solution slowly and stir. The resulting solids are filtered and collected. The collected solid was recrystallized from MC and MeOH to obtain a solid form of compound 135-3 (54 g, 51%).

4) Preparation of compound 135

4- (4-bromophenyl) -2,6-diphenylpyrimidine (11.8 g, 0.030 mol) was added to a solution of Compound 135-3 (9 g, 0.030 mol) mol) in toluene (toluene) was dissolved in _{100 mL Pd 2 (dba) 3} (2.8 g, 0.003 mol), tri-tert-butylphosphine (Tri-tert-butylphosphine) ( 1.2 g, 0.006 mol), sodium tert Sodium tert-butoxide (5.7 g, 0.062 mol) was added thereto and stirred at 100 DEG C for 15 hours. After completion of the reaction, the solution was cooled to room temperature, and the resulting solid was filtered to obtain Compound 135 (9.4 g, 52%) after drying.

Except that Intermediate F in the following Table 4 was used instead of 4- (4-bromophenyl) -2,6-diphenylpyrimidine in Production Example 2 The target compound was synthesized in the same manner as in Preparation Example 2,

In the same manner as in Preparation Example 2, except that benzoyl chloride was used instead of intermediate G in Table 5, 4- (4-bromophenyl) -2,6-diphenylpyrimidine (4- (4-bromophenyl) , 6-diphenylpyrimidine) was used instead of Intermediate H in Table 5, the target compound was synthesized.

In the same manner as in Preparation Example 2, except that Intermediate I of the following Table 6 was used instead of 2-bromoaniline and 4- (4-bromophenyl) -2,6-diphenylpyrimidine (4- (4- bromophenyl) -2,6-diphenylpyrimidine) was used instead of Intermediate J in Table 6, the target compound was synthesized.

< Manufacturing example  3> Preparation of Compound 237

1) Preparation of compound 237-1

(100 g, 0.621 mol) and 2-bromoaniline (96 g, 0.558 mol) were added to a solution of (1 H-indol-3-yl) boronic acid Pd (PPh ₃ ) ₄ (35.8 g, 0.031 mol) and NaHCO ₃ (156.5 g, 1.863 mol) were added to toluene (Toluene), EtOH and H ₂ O Lt; 0 &gt; C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a liquid form compound 237-1 (94 g, 72%).

2) Preparation of compound 237-2

Compound 237-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol) are dissolved in 1200 mL of MC. 4-Bromobenzoyl chloride (108.9 g, 0.496 mol) is dissolved in 300 mL of MC, and then slowly added dropwise to the mixture at 0 ° C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain a liquid form compound 237-2 (150 g, 85%).

3) Preparation of compound 237-3

Compound 237-2 (150 g, 0.383 mol) is dissolved in 1500 mL of Nitrobenzene, and then POCl ₃ (35 mL, 0.383 mol) is slowly added dropwise. And reacted at 140 캜 for 15 hours. After completion of reaction, add NaHCO ₃ dissolved in distilled water to the reaction solution slowly and stir. The resulting solids are filtered and collected. The collected solid was recrystallized from MC and MeOH to obtain a solid compound 237-3 (68 g, 48%).

4) Preparation of compound 237-4

(9.9 g, 0.039 mol), KOAc (7.6 g, 0.078 mol), PdCl ₂ (dppf) (0.07 mol), Compound 237-3 (10 g, 0.026 mol), bis (pinacolato diboron) 0.9 g, 0.0013 mol) is dissolved in 1,4-dioxane (200 mL) and reacted at 90 ° C. for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. Thereafter, it was dried over anhydrous MgSO _4, and then the solvent was removed by a rotary evaporator to obtain a compound 237-4 (10 g, 91%).

5) Preparation of compound 237-5

Compound 237-4 (8 g, 0.019 mol), 2-bromo-4,6-diphenyl-1,3,5-triazine ) (5.9 g, 0.019 mol) in toluene _{(toluene), EtOH, H 2} O 80 mL: 10 mL: was dissolved in _{10 mL Pd (PPh 3) 4} (1.1 g, 0.0009 mol) and K ₂ CO ₃ (7.8 g, 0.057 mol), and the mixture is stirred at 100 ° C for 5 hours. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain Compound 237-5 (7.4 g, 75%).

6) Preparation of compound 237

Compound 237-5 (7.4 g, 0.014 mol) and bromobenzene (3.2 g, 0.021 mol) were dissolved in toluene (100 mL) and Pd ₂ (dba) ₃ (1.2 g, 0.0014 mol) Tri-tert-butylphosphine (0.5 g, 0.0028 mol) and sodium tert-butoxide (2.7 g, 0.028 mol) were added and stirred at 100 ° C for 15 hours. After completion of the reaction, the solution was cooled to room temperature, and the resulting solid was filtered to obtain Compound 237 (6.5 g, 77%) after drying.

Except that 2-bromo-4,6-diphenyl-1,3,5-triazine was used instead of 2-bromo-4,6-diphenyl- K, the target compound was synthesized.

In the same manner as in Preparation Example 3, except that 4-bromobenzoyl chloride was replaced with Intermediate L of the following Table 8 and 2-bromo-4,6-diphenyl-1,3,5-triazine (2 -bromo-4,6-diphenyl-1,3,5-triazine) was used instead of the intermediate M in the following Table 8, the target compound was synthesized.

In the same manner as in Preparation Example 3, except that 2-bromoaniline was used in place of Intermediate N in Table 9 below, 2-bromo-4,6-diphenyl-1,3,5-triazine was used instead of 2-bromoaniline, -4,6-diphenyl-1,3,5-triazine) was used instead of Intermediate O in the following Table 9, the target compound was synthesized.

< Manufacturing example  4> Preparation of Compound 345

1) Preparation of compound 345-1

(100 g, 0.621 mol) and 2-bromoaniline (96 g, 0.558 mol) were added to a solution of (1 H-indol-3-yl) boronic acid Pd (PPh ₃ ) ₄ (35.8 g, 0.031 mol) and NaHCO ₃ (156.5 g, 1.863 mol) were added to toluene (Toluene), EtOH and H ₂ O Lt; 0 &gt; C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain compound 345-1 in liquid form (94 g, 72%).

2) Preparation of compound 345-2

Compound 345-1 (94 g, 0.451 mol) and triethylamine (42 mL, 0.451 mol) are dissolved in 1200 mL of MC. Benzoyl chloride (69.7 g, 0.496 mol) is dissolved in 300 mL of MC and then slowly added dropwise to the mixture at 0 ° C. After completion of the reaction, MC and distilled water are added to the reaction solution to be extracted. After drying with anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator to obtain compound 345-2 (112 g, 80%) in liquid form.

3) Preparation of compound 345-3

Compound 345-2 (112 g, 0.358 mol) is dissolved in 1000 mL of Nitrobenzene, and POCl ₃ (33 mL, 0.358 mol) is slowly added dropwise. And reacted at 140 캜 for 15 hours. After completion of reaction, add NaHCO ₃ dissolved in distilled water to the reaction solution slowly and stir. The resulting solids are filtered and collected. The collected solid was recrystallized from MC and MeOH to obtain 345-3 (54 g, 51%) of solid form.

4) Preparation of compound 345

4-yl) -6- (4-bromophenyl) pyrimidine (2.4 g, 0.030 mol) (4.7 g, 0.030 mol) was dissolved in 100 mL of toluene and then Pd ₂ (dba) ₃ (2.8 g, 0.030 mol) was dissolved in 100 mL of toluene. g, 0.003 mol), tri-tert-butylphosphine (1.2 g, 0.006 mol) and sodium tert-butoxide (5.7 g, 0.062 mol) Gt; 100 C &lt; / RTI &gt; After completion of the reaction, the solution was cooled to room temperature, and the resulting solid was filtered to obtain Compound 345 (15 g, 60%) after drying.

Di ((1,1 ') - biphenyl) -4-yl) -6- (4-bromophenyl) pyrimidine -biphenyl] -4-yl) -6- (4-bromophenyl) pyrimidine was used instead of Intermediate P in the following Table 10 to synthesize the desired compound.

In the same manner as in the above Production Example 4, except that the intermediate Q shown in the following Table 11 was used in place of benzoyl chloride and 2,4-di ([1,1 '] -biphenyl) -4-yl) -6- Except that Intermediate R in Table 11 was used instead of 2,4-di ([1,1'-biphenyl] -4-yl) -6- (4-bromophenyl) pyrimidine. And the desired compound was synthesized.

([1,1 '] - biphenyl) -4-yl) -6- (2-bromoaniline) was prepared in the same manner as in Preparation Example 4, Except that Intermediate T in Table 12 was used instead of 2,4-di ([1,1'-biphenyl] -4-yl) -6- (4-bromophenyl) pyrimidine The target compound was synthesized by the same method as Preparation Example 4.

The remaining compounds other than the compounds shown in Tables 1 to 12 were prepared in the same manner as described in the above Production Examples.

The following Tables 13 and 14 are the 1 H NMR data and the FD-MS data of the synthesized compound. From the following data, it can be confirmed that the desired compound is synthesized.

NO ^One 1 H NMR ( CDCl ₃ , 300Mz ) One (2H, d), 8.55 (1H, d), 8.42 (1H, d), 8.36 (4H, d), 7.96-7.85 (6H, m), 7.62-7.50 1H, &lt; / RTI &gt; t), 7.16 (1H, t) 2 (1H, m), 7.35 (1H, t), 7.95 (1H, d) 7.16 (1H, t) 4 (8H, m), 7.75 (2H, d), 7.62-7.35 (12H, m), 7.60 7.25 (2H, d), 7.16 (1H, t) 6 (1H, d), 8.42 (1H, d), 8.30 (2H, d), 8.23 d), 7.62-7.49 (12 H, m), 7.16 (1 H, t) 7 (2H, d), 8.55 (1H, d), 8.42 (1H, d), 7.96 m), 7.16 (1 H, t) 8 (1H, s), 7.94-7.75 (14H, m), 7.62-7.41 (1H, d) 12H, m), 7.16 (1 H, t) 16 (1H, d), 8.24 (1H, d), 8.24 (1H, d) m), 7.62-7.49 (13H, m), 7.35 (1H, t), 7.16 21 (1H, d), 8.23 (1H, d), 8.23 (1H, d) , 7.94-7.75 (12H, m), 7.62-7.41 (14H, m), 7.16 (1H, t) 26 (1H, m), 7.62-7.49 (11H, m), 7.35 (1H, d) 1H, t), 7.25 (2H, d), 7.16 (1H, t) 28 (2H, d), 7.62 (1H, d), 8.42 (1H, d), 8.45 7.35 (12 H, m), 7.16 (1 H, t) 31 (1H, s), 7.96-7.85 (12H, m), 7.75 (4H, d), 8.30 d), 7.62-7.41 (12H, m), 7.25 (2H, d), 7.16 33 d), 7.94 (2H, d), 7.85 (4H, d), 8.42 (2H, , 7.74 (2H, t), 7.62-7.50 (5H, m), 7.35 (1H, t), 7.25-7.16 35 (1H, m), 7.35 (1H, m), 7.73 (1H, t), 7.62 7.16 (1H, t) 37 (1H, s), 7.94-7.85 (8H, m), 7.73 (1H, t), 7.62-7.49 (11H, m), 8.42-8.33 7.35 (1H, t), 7.16 (1H, t) 39 (7H, m), 7.75 (2H, d), 7.73 (1H, t), 7.62 (1H, 7.35 (12 H, m), 7.16 (1 H, t) 41 (8H, m), 7.75-7.73 (5H, m), 7.62-7.35 (12H, m), 7.25 (4H, d), 8.42-8.33 ), 7.16 (1H, t) 42 m), 7.16 (1 H, t), 7.94-7.75 (13 H, m), 7.62-7.35 (12 H, m) 45 (2H, d), 7.94 (1H, d), 8.01 (1H, d) , 7.90 (1H, d), 7.72-7.50 (13H, m), 7.35 59 (1H, s), 7.96-7.94 (7H, m), 7.79-7.41 (1H, d) 23H, m), 7.16 (1 H, t) 65 (1H, s), 8.09-7.85 (10H, m), 7.62-7.49 (2H, d), 8.35 13H, m), 7.35 (1H, t), 7.25 (2H, d), 7.16 66 d), 8.69 (2H, d), 8.55 (1H, d), 8.42-8.30 (6H, m), 8.15 7.50 (13H, m), 7.35 (1H, t), 7.16 (1H, t) 68 (1H, d), 8.23 (1H, d), 8.32 (1H, d) , 8.15 (1H, d), 7.96-7.88 (8H, m), 7.70-7.49 (13H, m), 7.35 70 (2H, d), 8.42 (1H, d), 8.38 (2H, 7.35 (14 H, m), 7.16 (1 H, t) 73 (1H, d), 7.73 (1H, d), 7.73 (1H, d) t), 7.62-7.35 (13H, m), 7.16 (1H, t) 74 (2H, d), 8.23 (1H, s), 7.94-7.87 (7H, d) m), 7.75 (2H, d), 7.73 (1H, t), 7.62-7.41 (13H, 77 d), 8.19 (1H, d), 7.96-7.85 (7H, m), 7.62-7.50 (2H, 10H, m), 7.35 (2H, t), 7.20 (1H, t), 7.16 78 d), 8.19 (1H, d), 7.94-7.85 (11H, m), 7.62-7.50 (2H, 10H, m), 7.35 (1H, t), 7.20 ~ 7.16 (3H, t) 88 d), 8.09 (1H, d), 7.94-7.78 (9H, m), 7.62-7.50 (2H, (1H, m), 7.38 (1H, t), 7.35 (1H, t), 7.28 93 d), 8.30 (2H, d), 8.23 (1H, s), 8.09 (1H, d) , 7.94-7.73 (10H, m), 7.62-7.50 (10H, m), 7.38-7.28 (3H, m), 7.16 96 (8H, m), 7.35 (2H, d), 8.42 (2H, d), 8.42 1H, &lt; / RTI &gt; t), 7.16 (1H, t) 100 m, 7.25 (2H, d), 7.16 (2H, d), 8.42 (1H, 1H, t) 101 m), 7.16 (1H, t), 8.42 (1H, d), 7.94-7.75 (14H, 104 (2H, d), 8.27 (1H, d), 8.42 (1H, d) , 8.05 (1H, s), 7.96-7.85 (9H, m), 7.70-7.50 (12H, m), 7.35 105 d), 8.15 (1H, d), 8.55 (1H, d), 8.42 (1H, d), 8.36 , 7.96-7.85 (7H, m), 7.75-7.50 (12H, m), 7.35 108 (6H, m), 7.75 (4H, d), 8.04 (2H, d) d), 7.62-7.35 (15H, m), 7.16 (1H, t) 115 (1H, d), 8.55 (1H, d), 8.45-8.42 (2H, d), 8.30-8.20 (5H, m), 7.94-7.85 (10H, m), 7.62-7.35 ), 7.25 (2H, d), 7.16 (1H, t) 117 (1H, d), 7.62 (1H, d), 8.62 (1H, d) 7.35 (14H, m), 7.25 (4H, m), 7.16 (1H, t) 120 d), 8.25 (1H, d), 8.23 (1H, d), 8.20 (1H, , 7.94-7.85 (10H, m), 7.75 (4H, d), 7.73 (2H, d), 7.62-7.35 131 d), 8.06 (1H, d), 8.42 (1H, d), 8.09 , 7.94-7.84 (5H, m), 7.62-7.46 (13H, m), 7.35 132 (2H, d), 8.23 (1H, s), 8.42 (1H, d) , 8.06 (1H, d), 7.94-7.84 (7H, m), 7.62-7.49 (13H, m), 7.35 134 (8H, m), 7.65 (2H, d), 7.50-7.49 (7H, m), 8.42-8.36 7.35 (1H, t), 7.16 (1H, t) 135 (1H, d), 8.42 (1H, d), 8.35 (2H, d), 8.23 t), 7.55-7.49 (7H, m), 7.35 (1H, t), 7.16 137 (1H, d), 7.65 (2H, t), 7.50-7.85 (2H, d), 8.42-8.36 7.35 (8H, m), 7.25 (2H, d), 7.16 (1H, t) 139 (2H, d), 7.94-7.85 (12H, m), 7.75 (2H, d) d), 7.65 (2H, t), 7.55-7.35 (8H, m), 7.16 141 (8H, m), 8.42 (1H, d), 8.30-8.19 (7H, m), 7.94-7.75 7.16 (1H, t) 143 m), 7.94-7.79 (5H, m), 7.65-7.49 (11H, m), 8.42-8.36 (5H, m), 8.24-8.12 ), 7.35 (1H, t), 7.16 (1H, t) 148 m), 7.16 (1H, t), 8.42 (1H, d), 8.30 149 (1H, d), 8.42 (1H, d), 8.24-8.19 (3H, d), 7.94-7.35 (25H, m), 7.25 1H, t) 152 d), 8.20 (1H, d), 8.20 (1H, d), 8.45 , 8.19 (2H, d), 7.94-7.85 (7H, m), 7.65-7.49 (4H, m), 7.35 155 (1H, d), 8.42 (1H, d), 8.23 (1H, s), 8.19 (2H, d), 7.94-7.85 7H, m), 7.35 (1H, t), 7.25 (2H, d), 7.16 156 d), 8.20 (1H, d), 8.19 (2H, d), 8.33 , 7.94-7.85 (7H, m), 7.65-7.49 (6H, m), 7.35 157 d), 8.19 (2H, d), 7.94-7.85 (11H, d), 8.42 m), 7.65-7.49 (6H, m), 7.35 (1H, t), 7.29 158 d), 8.19 (2H, d), 7.94-7.85 (9H, m), 7.73-7.49 (2H, 8H, m), 7.35-7.29 (3H, m), 7.16 (1H, t) 159 (1H, d), 8.42 (1H, d), 8.19 (2H, d), 7.96-7.85 (14H, m), 7.75 8H, m), 7.25-7.16 (7H, m), 161 d), 8.19 (2H, d), 7.94-7.85 (8H, m), 7.74-7.65 (2H, 4H, d), 7.49 (1H, t), 7.35 (1H, t), 7.25-7.16 (7H, 165 (2H, d), 8.19 (2H, d), 7.94-7.85 (4H, m), 7.68-7.60 (4H, m), 8.42-8.36 7.50 (7H, t), 7.35 (1H, t), 7.16 (1H, t) 168 (6H, m), 7.50-7.55 (8H, m), 8.08-8.36 (3H, d), 8.42-8.36 , &lt; / RTI &gt; m), 7.25 (2H, d), 7.16 169 (8H, m), 7.16 (1H, t), 8.42-8.30 (5H, m), 8.23-8.19 (4H, m), 7.94-7.65 ) 187 (9H, m), 7.77-7.60 (9H, m), 8.24-8.11 (6H, m) 7.50-7.35 (9H, m), 7.16 (1H, t) 192 (1H, m), 7.16 (1H, t), 8.45-7.91 (18H, m), 7.75-7.65 195 (2H, d), 8.15 (2H, d), 8.05-7.91 (10H, m), 7.65-7.49 (11H, m), 7.35 1H, &lt; / RTI &gt; t), 7.16 (1H, t) 203 (1H, m), 7.65 (2H, t), 7.54-7.49 (5H, m), 8.42-8.36 7.39 (1H, t), 7.36 (1H, t) 205 (1H, d), 8.42 (1H, d), 8.35 (2H, d) m), 7.69-7.49 (9H, m), 7.39-7.25 (5H, m), 7.16 209 (9H, m), 7.35 (1H, t), 8.45-8.36 (4H, d), 8.19 7.16 (1H, t) 212 (2H, d), 7.94-7.85 (11H, m), 7.73-7.49 (11H, m), 8.45-8.32 7.35 (1H, t), 7.16 (1H, t) 213 (1H, d), 8.42 (2H, d), 8.36 (4H, d), 8.21 d), 7.55-7.50 (7H, m), 7.35 (1H, t), 7.16 218 d, 8.84 (1H, d), 8.55 (1H, d), 8.44 (1H, s), 8.42-8.36 (1H, m), 7.75-7.62 (6H, m), 7.50-7.55 (7H, m) 219 d, 8.84 (1H, d), 8.54 (1H, d), 8.44-8.30 (6H, m), 8.23 11H, m), 7.75-7.62 (6H, m), 7.50-7.35 (7H, m), 7.16 222 (2H, d), 8.30 (4H, d), 8.23 (1H, s), 8.17 (1H, d), 7.94-7.63 (21H, m), 7.49-7.55 (7H, m), 7.16 228 d), 8.17 (1H, d), 8.44 (1H, d), 8.42 (1H, t), 7.96-7.85 (14H, m), 7.75-7.62 (6H, m), 7.50-7.55 (7H, m) 229 (1H, d), 8.84 (1H, d), 8.55 (1H, d), 8.44 7.60 (8H, m), 7.50 ~ 7.35 (8H, m), 7.16 (1H, t) 234 (2H, d), 8.16 (1H, d), 8.06 (1H, d) , 7.96-7.84 (11H, m), 7.75 (2H, d), 7.65 (2H, t), 7.50-7.55 (10H, m) 236 (2H, d), 8.16 (1H, d), 8.06 (1H, d) , 7.94-7.85 (13H, m), 7.75 (2H, d), 7.65-7.35 (12H, m) 237 (2H, d), 8.55 (1H, d), 8.36 (4H, d), 8.20 (1H, d), 7.96-7.94 12H, m), 7.35 (1H, t), 7.16 (1H, t) 238 (1H, d), 7.94 (4H, d), 8.30 (2H, d) , 7.70-7.49 (12H, m), 7.35 (1H, t), 7.16 (1H, t) 240 (1H, d), 7.60 (1H, d), 8.40 (1H, d) (15H, m), 7.25 (2H, d), 7.16 (1H, t) 242 (1H, d), 8.30 (2H, d), 8.55 (1H, d), 8.30 15H, m), 7.16 (1H, t) 248 (1H, d), 8.55 (1H, d), 8.35-8.20 (5H, m), 7.94-7.85 (5H, m), 7.62-7.50 7.35 (1H, t), 7.16 (1H, t) 250 (1H, d), 7.94 (4H, d), 7.85 (1H, d), 8.36 t), 7.70 ~ 7.35 (17H, m), 7.25 (2H, d), 7.16 251 (2H, d), 7.85 (2H, d), 7.75 (1H, d), 8.85 17H, m), 7.16 (1 H, t) 253 d), 8.20 (1H, d), 7.96-7.94 (7H, m), 7.70-7.35 (1H, 19H, m), 7.25 (4H, d), 7.16 (1H, t) 259 (2H, d), 8.55 (1H, d), 8.23 (1H, s), 8.20 (1H, d), 7.94-7.85 (11H, m), 7.70-7.49 1H, t), 7.25 (2H, d), 7.16 (1H, t) 263 (2H, d), 8.55 (1H, d), 8.20 (1H, d), 7.96-7.85 (11H, m), 7.70-7.41 1H, t) 264 (2H, d), 8.55 (1H, d), 8.30 (4H, d), 8.23 (1H, s), 8.20 d), 7.16 (1 H, t) 267 (2H, d), 7.85 (1H, d), 7.85 (1H, d), 8.38 , 7.70-7.50 (13H, m), 7.35 (1H, d), 7.16 (1H, t) 270 (2H, m), 7.25 (2H, d, J = 8.55 (1H, d), 8.38 (1H, s), 8.36 d), 7.16 (1 H, t) 273 (7H, m), 7.70-7.55 (18H, m), 7.25 (4H, d), 7.30 , &lt; / RTI &gt; d), 7.16 (1H, t) 277 d, 8.30 (2H, d), 7.96-7.85 (1H, d) 7H, m), 7.70-7.50 (15H, m), 7.35 (1H, t), 7.25 278 (2H, d), 8.55 (1H, d), 8.37-8.30 (5H, m), 8.20 (1H, d), 7.96-7.85 M), 7.70-7.50 (15H, m), 7.35 (1H, t), 7.25-7.16 (5H, m) 282 d), 8.23 (1H, s), 8.20 (1H, d), 8.37 d), 7.96-7.85 (11H, m), 7.70-7.49 (16H, m), 7.35 283 (1H, d), 8.08 (1H, d), 8.05 (1H, d) , 8.06 (1H, d), 7.98-7.84 (6H, m), 7.70-7.35 (18H, m), 7.16 284 (1H, d), 8.09 (1H, d), 7.94-7.50 (20H, m), 7.38-7.25 5H, m), 7.16 (1H, t), 1.69 (6H, s) 288 (1H, m), 7.70-7.50 (9H, m), 7.35 (2H, d) 1H, t), 7.25 (2H, d), 7.16 (1H, t) 290 (1H, d), 8.02 (1H, m), 7.70-7.49 (1H, 10H, m), 7.35 (1H, t), 7.25 (2H, d), 7.16 292 (2H, d), 8.55 (1H, d), 8.20 (1H, d), 7.96-7.35 (25H, m), 7.25 293 (2H, d), 7.16 (1H, d), 8.20 (1H, d) t) 296 (2H, d), 8.05 (1H, d), 8.08 (1H, d) t), 7.25 (2H, d), 7.16 (1H, t), 7.96-7.85 (10H, m), 7.70-7.50 (13H, 299 (2H, d), 8.23-8.15 (3H, m), 7.96-7.85 (10H, m) (1H, t), 7.25 (2H, d), 7.16 (1H, t) 300 d), 7.85 (3H, d), 8.04 (3H, s), 7.96-7.94 (4H, d) t), 7.70 ~ 7.35 (20H, m), 7.25 (2H, d), 7.16 303 d, 8.95 (1H, d), 8.69 (2H, d), 8.55 (1H, d), 8.30-8.20 (6H, m), 8.06 (1H, d), 7.95-7.35 27H, m), 7.25 (2H, d), 7.16 (1H, t) 304 (1H, d), 8.06 (1H, d), 8.05 (1H, d) ), 7.94-7.41 (29H, m), 7.25 (2H, d), 7.16 305 (1H, d), 8.57 (1H, d), 8.38-8.30 (7H, m), 8.20 d), 7.94 (3H, d), 7.85 (1H, t), 7.73-7.50 (19H, m), 7.35 306 (1H, d), 8.20 (1H, d), 8.55 (1H, d), 8.35 , 8.08 (1H, d), 8.06 (1H, d), 7.98-7.94 (3H, d), 8.85-8.84 (2H, t), 7.74-7.39 (19H, 308 (2H, d), 8.06 (1H, d), 7.96-7.94 (4H, m), 7.85 (1H, d), 7.70-7.50 (13H, m), 7.39-7.16 (9H, m) 313 d), 7.85 (3H, d), 7.60-7.35 (1H, d) 17H, m), 7.25 (2H, d), 7.16 (1H, t) 321 (1H, d), 8.23 (1H, s), 8.20 (1H, d), 7.94-7.85 (12H, m), 7.70 (1H, t), 7.55-7.49 1H, t), 7.28 (2H, t), 7.16 (1H, t) 324 (1H, d), 7.70 (1H, d), 8.30 (1H, d) t), 7.55-7.28 (10H, m), 7.16 (1H, t) 325 (1H, d), 8.20 (1H, d), 7.96-7.85 (13H, m), 7.75 1H, t) 332 (2H, d), 8.12 (1H, d), 7.96-7.70 (11H, m), 7.50 7.16 (15 H, m) 336 (1H, d), 8.55 (1H, d), 8.30-8.20 (7H, m), 8.12 (1H, d), 7.94-7.70 (15H, m), 7.59-7.28 7.16 (1H, t) 339 (7H, m), 7.35-7.28 (1H, d), 7.30 (1H, 5H, &lt; / RTI &gt; m), 7.16 (1H, t) 343 (13H, m), 7.75 (3H, t), 7.50-7.86 (1H, d), 8.35 7.28 (10 H, m), 7.16 (1 H, t) 345 m), 7.75 (4H, d), 7.70 (1H, t), 7.49-7.16 (17H, m) 352 (7H, m), 7.75 (5H, d), 7.50-7.28 (12H, m), 8.36 (2H, d), 8.24-8.20 7.16 (1H, t) 353 (13H, m), 7.50-7.28 (10H, m), 7.16 (1H, t), 8.35-8.30 (4H, d), 8.23-8.20 ) 363 (1H, d), 8.51 (1H, d), 8.23 (1H, s), 8.20 2H, t), 7.55-7.49 (7H, m), 7.35-7.28 (3H, t), 7.16 365 (1H, d), 8.03 (1H, s), 7.94-7.86 (9H, m), 7.75-7.69 (3H, 7.55-7.49 (7H, m), 7.35-7.28 (3H, m), 7.16 (1H, t) 367 (9H, m), 7.35-7.28 (3H, m), 8.06-7.86 (10H, m) 7.16 (1H, t) 370 d, 8.30 (2H, d), 7.94-7.85 (8H, d), 8.45 m), 7.70 (1, t), 7.56-7.49 (2H, t), 7.35-7.28 (4H, d), 7.16 372 (8H, m), 7.70 (1H, t), 7.55-7.85 (2H, d) 7.49 (4H, m), 7.35-7.29 (5H, m), 7.16 (1H, t) 373 (2H, d), 7.94-7.86 (12H, m), 7.70 (1H, t), 7.55 7.49 (4H, m), 7.35-7.28 (5H, m), 7.16 (1H, t) 374 (2H, t), 7.61 (1H, d), 8.02 (2H, d) 7.49 (5H, m), 7.35-7.28 (5H, m), 7.16 (1H, t) 376 (1H, d), 8.09 (1H, d), 7.94-7.70 (17H, m), 7.61-7.28 (15H, m), 7.16 379 m), 7.75-7.70 (3H, t), 7.50-7.16 (17H, m), 7.20-7.86 (1H, 380 (11H, m), 7.75-7.70 (3H, t), 7.50-7.28 (14H, d), 8.35-8.30 , &lt; / RTI &gt; m), 7.16 (1H, t) 381 (1H, d), 8.23 (1H, s), 8.20 (1H, d), 7.94-7.85 (15H, m), 7.70 (1H, t), 7.55-7.49 7.25 (9 H, m), 7.16 (1 H, t) 382 (7H, m), 7.25-7.16 (1H, m), 7.30 (1H, d) 10H, m) 384 (2H, d), 8.55 (1H, d), 8.36 (4H, d), 8.20 (1H, d), 7.96-7.85 d), 7.50-7.49 (7H, m), 7.39-7.28 (7H, m), 7.16 388 (8H, m), 7.70 (2 H, d), 8.08-8.04 (4H, m), 7.94-7.85 ), 7.50 (6H, s), 7.35 (1H, t), 7.16 (1H, t) 391 (9H, m), 7.75 (2H, d), 8.36-8.33 (4H, d) 7.64 (7H, m), 7.50-7.35 (8H, m), 7.25 (2H, d), 7.16 395 (7H, m), 8.49 (1H, s), 8.85 (1H, d), 8.55 7.16 (1H, t) 396 (1H, d), 8.06 (1H, d), 8.45 (1H, d) t), 7.52-7.46 (8H, m), 7.35-7.25 (5H, m), 7.16 (1H, t) 397 (1H, d), 8.02 (1H, d), 7.94-7.84 (13H, m), 7.70 t), 7.55-7.49 (8H, m), 7.35-7.16 (8H, m) 398 (1H, d), 8.08 (1H, d), 8.08 (1H, d) , 7.94-7.86 (13H, m), 7.74-7.64 (3H, d), 7.55-7.28 (12H, m), 7.16 399 (2H, d), 8.55 (2H, d), 8.36 (4H, d), 8.06-7.94 (6H, m), 7.85 1H, t), 7.25 (2H, d), 7.16 (1H, t) 400 (2H, d), 8.25 (1H, d), 8.23 (1H, d) (1H, d), 8.11 (1H, d), 8.03 (1H, s), 8.06 (1H, d), 7.94 ), 7.25 (2H, d), 7.16 (1H, t) 401 (1H, d), 8.11 (1H, d), 7.96-7.90 (1H, 8H, m), 7.72-7.49 (13H, m), 7.35 (1H, t), 7.16

compound FD-MS compound FD-MS One m / z = 601.71 (C42H27N5 = 601.22) 2 m / z = 600.72 (C43H28N4 = 600.23) 3 m / z = 600.72 (C43H28N4 = 600.23) 4 m / z = 677.81 (C48 H31 N5 = 677.23) 5 m / z = 676.81 (C49H32N4 = 676.26) 6 m / z = 676.82 (C49 H32 N4 = 676.26) 7 m / z = 753.90 (C54 H35 N5 = 753.28) 8 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 9 m / z = 601.71 (C42H27N5 = 601.22) 10 m / z = 599.73 (C44H29N3 = 599.23) 11 m / z = 599.73 (C44H29N3 = 599.23) 12 m / z = 675.83 (C50H33N3 = 675.26) 13 m / z = 570.63 (C39H27N2O5 = 570.18) 14 m / z = 651.77 (C46 H29 N5 = 651.24) 15 m / z = 650.78 (C 47 H 30 N 4 -650.24) 16 m / z = 650.78 (C47H30N4 = 650.24) 17 m / z = 727.87 (C52 H33 N5 = 727.27) 18 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 19 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 20 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 21 m / z = 802.98 (C59H38N4 = 802.31) 22 m / z = 651.77 (C46 H29 N5 = 651.24) 23 m / z = 620.69 (C43H29N2O6 = 620.20) 24 m / z = 677.81 (C48 H31 N5 = 677.25) 25 m / z = 676.82 (C49 H32 N4 = 676.26) 26 m / z = 676.82 (C49 H32 N4 = 676.26) 27 m / z = 753.90 (C54 H35 N5 = 753.28) 28 m / z = 752.91 (C 55 H 36 N 4 = 752.29) 29 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 30 m / z = 830.00 (C60H39N5 = 829.31) 31 m / z = 829.01 (C61 H40 N4 = 828.32) 32 m / z = 829.01 (C61 H40 N4 = 828.32) 33 m / z = 677/81 (C48 H31 N5 = 677.25) 34 m / z = 646.73 (C45H31N2OP = 646.21) 35 m / z = 601.71 (C42H27N5 = 601.22) 36 m / z = 600.72 (C43H28N4 = 600.23) 37 m / z = 600.72 (C43H28N4 = 600.23) 38 m / z = 677.81 (C48 H31 N5 = 677.25) 39 m / z = 676.82 (C49 H32 N4 = 676.26) 40 m / z = 676.82 (C49 H32 N4 = 676.26) 41 m / z = 753.90 (C54 H35 N5 = 753.28) 42 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 43 m / z = 601.71 (C42H27N5 = 601.22) 44 m / z = 570.63 (C39H27N2O5 = 570.18) 45 m / z = 651.77 (C46 H29 N5 = 651.24) 46 m / z = 650.78 (C47H30N4 = 650.24) 47 m / z = 650.78 (C47H30N4 = 650.24) 48 m / z = 727.87 (C52 H33 N5 = 727.27) 49 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 50 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 51 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 52 m / z = 802.98 (C59 H38 N4 = 802.30) 53 m / z = 651.77 (c46H29N5 = 651.24) 54 m / z = 650.78 (C47H30N4 = 650.24) 55 m / z = 650.78 (C47H30N4 = 650.24) 56 m / z = 727.87 (C52 H33 N5 = 727.27) 57 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 58 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 59 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 60 m / z = 802.91 (C59H38N4 = 802.31) 61 m / z = 651.77 (C46 H29 N5 = 651.24) 62 m / z = 650.78 (C47H30N4 = 650.24) 63 m / z = 650.78 (C47H30N4 = 650.24) 64 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 65 m / z = 802.98 (C59H38N4 = 802.31) 66 m / z = 751.89 (C54 H33 N5 = 751.27) 67 m / z = 750.90 (C 55 H 34 N 4 = 750.27) 68 m / z = 750.90 (C 55 H 34 N 4 = 750.27) 69 m / z = 750.90 (C 55 H 34 N 4 = 750.27) 70 m / z = 753.90 (C54 H35 N5 = 753.28) 71 m / z = 677.81 (C48 H31 N5 = 677.25) 72 m / z = 676.82 (C49 H32 N4 = 676.26) 73 m / z = 676.82 (C49 H32 N4 = 676.26) 74 m / z = 676.82 (C49 H32 N4 = 676.26) 75 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 76 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 77 m / z = 690.81 (C48H30N6 = 690.25) 78 m / z = 766.90 (C54 H34 N6 = 766.28) 79 m / z = 766.90 (C54 H32 N6 = 766.28) 80 m / z = 689.82 (C49 H31 N5 = 689.25) 81 m / z = 765.92 (C 55 H 35 N 5 = 765.28) 82 m / z = 765.92 (C 55 H 35 N 5 = 765.28) 83 m / z = 689.82 (C49 H31 N5 = 689.25) 84 m / z = 765.92 (C 55 H 35 N 5 = 765.28) 85 m / z = 765.92 (C 55 H 35 N 5 = 765.28) 86 m / z = 765.92 (C 55 H 35 N 5 = 765.28) 87 m / z = 765.92 (C 55 H 35 N 5 = 765.28) 88 m / z = 717.87 (C51 H35 N5 = 717.28) 89 m / z = 716.88 (C52H36N4 = 716.29) 90 m / z = 716.88 (C52H36N4 = 716.29) 91 m / z = 716.88 (C52H36N4 = 716.29) 92 m / z = 793.97 (C 57 H 39 N 5 = 793.32) 93 m / z = 792.98 (C 58 H 40 N 4 = 792.32) 94 m / z = 792.98 (C 58 H 40 N 4 = 792.32) 95 m / z = 792.98 (C 58 H 40 N 4 = 792.32) 96 m / z = 626.72 (C43H26N6 = 626.22) 97 m / z = 625.73 (C44H27N5 = 625.22) 98 m / z = 625.73 (C44H27N5 = 625.22) 99 m / z = 625.73 (C44H27N5 = 625.22) 100 m / z = 702.82 (C49H30N6 = 702.25) 101 m / z = 702.82 (C49H30N6 = 702.25) 102 m / z = 701.83 (C50 H31 N5 = 701.25) 103 m / z = 701.83 (C50 H31 N5 = 701.25) 104 m / z = 777.93 (C56.35N5 = 777.28) 105 m / z = 701.83 (C50 H31 N5 = 701.25) 106 m / z = 776.94 (C 57 H 36 N 4 = 776.29) 107 m / z = 700.84 (C51 H32 N4 = 700.26) 108 m / z = 753.90 (C54 H35 N5 = 753.28) 109 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 110 m / z = 651.77 (C46 H29 N5 = 651.24) 111 m / z = 650.78 (C47H30N4 = 650.24) 112 m / z = 650.78 (C47H30N4 = 650.24) 113 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 114 m / z = 802.98 (C59H38N4 = 802.31) 115 m / z = 802.98 (C59H38N4 = 802.31) 116 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 117 m / z = 802.98 (C59H38N4 = 802.31) 118 m / z = 802.98 (C59H38N4 = 802.31) 119 m / z = 777.93 (C56 H35 N5 = 777.28) 120 m / z = 879.07 (C65H42N4 = 878.34) 121 m / z = 651.77 (C46 H29 H5 = 651.24) 122 m / z = 650.78 (C47H30N4 = 650.24) 123 m / z = 650.78 (C47H30N4 = 650.24) 124 m / z = 727.87 (C52 H33 N5 = 727.27) 125 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 126 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 127 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 128 m / z = 802.98 (C59H38N4 = 802.31) 129 m / z = 651.77 (C46 H29 N5 = 651.24) 130 m / z = 620.69 (C43H29N2O6 = 620.20) 131 m / z = 727.87 (C52 H33 N5 = 727.27) 132 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 133 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 134 m / z = 601.71 (C42H27N5 = 601.22) 135 m / z = 600.72 (C43H28N4 = 600.23) 136 m / z = 600.72 (C43H28N4 = 600.23) 137 m / z = 677.81 (C48 H31 N5 = 677.25) 138 m / z = 676.82 (C49 H32 N4 = 676.26) 139 m / z = 676.82 (C49 H32 N4 = 676.26) 140 m / z = 753.90 (C54 H35 N5 = 753.28) 141 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 142 m / z = 601.71 (C42H27N5 = 601.22) 143 m / z = 651.77 (C46 H29 N5 = 651.24) 144 m / z = 650.78 (C47H30N4 = 650.24) 145 m / z = 650.78 (C47H30N4 = 650.24) 146 m / z = 727.87 (C52 H33 N5 = 727.27) 147 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 148 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 149 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 150 m / z = 802.98 (C59H38N4 = 802.31) 151 m / z = 651.77 (C46 H29 N5 = 651.24) 152 m / z = 548.69 (C39H24N4 = 548.20) 153 m / z = 677.81 (C48 H31 N5 = 677.25) 154 m / z = 676.82 (C49 H32 N4 = 676.26) 155 m / z = 676.82 (C49 H32 N4 = 676.26) 156 m / z = 624.74 (C45 H28 N4 = 624.23) 157 m / z = 700.84 (C51 H32 N4 = 700.26) 158 m / z = 700.84 (C51 H32 N4 = 700.26) 159 m / z = 830.00 (C60H39N5 = 829.32) 160 m / z = 829.01 (C61 H40 N4 = 828.32) 161 m / z = 677.81 (C48 H31 N5 = 677.25) 162 m / z = 675.83 (C50H33N3 = 675.26) 163 m / z = 751.93 (C56 H37 N3 = 751.29) 164 m / z = 646.73 (C45H31N2OP = 646.21) 165 m / z = 601.71 (C42H27N5 = 601.22) 166 m / z = 600.72 (C43H28N4 = 600.23) 167 m / z = 600.72 (C43H28N4 = 600.23) 168 m / z = 677.81 (C48 H31 N5 = 677.25) 169 m / z = 676.82 (C49 H32 N4 = 676.26) 170 m / z = 676.82 (C49 H32 N4 = 676.26) 171 m / z = 753.90 (C54 H35 N5 = 753.28) 172 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 173 m / z = 601.71 (C42H27N5 = 601.22) 174 m / z = 599.73 (C44H29N3 = 599.23) 175 m / z = 599.73 (C44H29N3 = 599.23) 176 m / z = 675.83 (C50H33N3 = 675.26) 177 m / z = 675.83 (C50H33N3 = 675.26) 178 m / z = 570.63 (C39H27N2O5 = 570.18) 179 m / z = 651.77 (C46 H29 N5 = 651.24) 180 m / z = 650.78 (C47H30N4 = 650.24) 181 m / z = 650.78 (C47H30N4 = 650.24) 182 m / z = 727.87 (C52 H33 N5 = 727.27) 183 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 184 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 185 m / z = 816.96 (C 58 H 36 N 6 = 816.30) 186 m / z = 816.96 (C 58 H 36 N 6 = 816.30) 187 m / z = 893.06 (C 64 H 40 N 6 = 892.33) 188 m / z = 651.77 (C46 H29 N5 = 651.24) 189 m / z = 650.78 (C47H30N4 = 650.24) 190 m / z = 650.78 (C47H30N4 = 650.24) 191 m / z = 817.95 (C 58 H 35 N 5 O = 817.28) 192 m / z = 816.96 (C59 H36 N4 O = 816.28) 193 m / z = 816.96 (C59 H36 N4 O = 816.28) 194 m / a = 651.77 (C46 H29 N5 = 651.24) 195 m / z = 650.78 (C47H30N4 = 650.24) 196 m / z = 650.78 (C47H30N4 = 650.24) 197 m / z = 727.87 (C52 H33 N5 = 727.27) 198 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 199 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 200 m / z = 834.01 (C 58 H 35 N 5 S = 833.26) 201 m / z = 833.02 (C59 H36 N4 S = 832.26) 202 m / a = 756.92 (C53 H32 N4 S = 756.23) 203 m / z = 691.79 (C48H29N5O = 691.23) 204 m / z = 691.79 (C48H29N4O = 691.23) 205 m / z = 766.90 (C 55 H 34 N 4 O = 766.27) 206 m / z = 766.90 (C 55 H 34 N 4 O = 766.27) 207 m / z = 701.83 (C50 H31 N5 = 701.25) 208 m / z = 700.84 (C51 H32 N4 = 700.26) 209 m / z = 707.85 (C48H29N5S = 707.21) 210 m / z = 706.86 (C49H30N4S = 706.21) 211 m / z = 782.96 (C 55 H 34 N 4 S = 782.25) 212 m / z = 782.96 (C 55 H 34 N 4 S = 782.25) 213 m / z = 725.85 (C52H31N5 = 725.25) 214 m / z = 724.86 (C 53 H 32 N 4 = 724.26) 215 m / z = 701.83 (C50 H31 N5 = 701.25) 216 m / z = 700.84 (C51 H32 N4 = 700.26) 217 m / z = 700.84 (C51 H32 N4 = 700.26) 218 m / z = 777.93 (C56 H35 N5 = 777.28) 219 m / z = 776.94 (C 57 H 36 N 4 = 776.29) 220 m / z = 776.94 (C 57 H 36 N 4 = 776.29) 221 m / z = 854.02 (C62H39N5 = 853.32) 222 m / z = 853.04 (C 63 H 40 N 4 = 852.32) 223 m / z = 701.83 (C50 H31 N5 = 701.25) 224 m / z = 670.75 (C47H31N2OP = 670.21) 225 m / z = 777.93 (C56 H35 N5 = 777.28) 226 m / z = 776.94 (C 57 H 36 N 4 = 776.29) 227 m / z = 827.00 (C61 H38 N4 = 826.31) 228 m / z = 854.02 (C62H39N5 = 853.32) 229 m / z = 853.04 (C 63 H 40 N 4 = 852.32) 230 m / z = 903.10 (C67H42N4 = 902.34) 231 m / z = 854.02 (C62H39N5 = 853.32) 232 m / z = 853.04 (C 63 H 40 N 4 = 852.32) 233 m / z = 777.93 (C56 H35 N5 = 777.28) 234 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 235 m / z = 802.98 (C59H38N4 = 802.31) 236 m / z = 802.98 (C59H38N4 = 802.31) 237 m / z = 601.71 (C42H27N5 = 601.22) 238 m / z = 600.72 (C43H28N4 = 600.23) 239 m / z = 600.72 (C43H28N4 = 600.23) 240 m / z = 677.81 (C48 H31 N5 = 677.25) 241 m / z = 676.82 (C49 H32 N4 = 676.26) 242 m / z = 676.82 (C49 H32 N4 = 676.26) 243 m / z = 753.90 (C54 H35 N4 = 753.28) 244 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 245 m / z = 601.71 (C42H27N4 = 601.22) 246 m / z = 570.63 (C39H27N2O5 = 570.18) 247 m / z = 651.77 (C46 H29 N5 = 651.24) 248 m / z = 650.78 (C47H30N4 = 650.24) 249 m / z = 650.78 (C47H30N4 = 650.24) 250 m / z = 727.87 (C52 H33 N5 = 727.27) 251 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 252 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 253 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 254 m / z = 802.98 (C59H38N4 = 802.31) 255 m / z = 651.77 (C46 H29 N5 = 651.24) 256 m / z = 620.69 (C43H29N2O6 = 620.20) 257 m / z = 677.81 (C48 H31 N5 = 677.25) 258 m / z = 676.82 (C49 H32 N4 = 676.26) 259 m / z = 676.82 (C49 H32 N4 = 676.26) 260 m / z = 753.90 (C54 H35 N5 = 753.28) 261 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 262 m / z = 752.29 (C 55 H 36 N 4 = 752.29) 263 m / z = 830.00 (C60H39N5 = 829.32) 264 m / z = 829.01 (C61 H40 N4 = 828.32) 265 m / z = 677.81 (C48 H31 N5 = 677.25) 266 m / z = 646.73 (C45H31N2OP = 646.21) 267 m / z = 601.71 (C42H27N5 = 601.22) 268 m / z = 600.72 (C43H28N4 = 600.23) 269 m / z = 600.72 (C43H28N4 = 600.23) 270 m / z = 677.81 (C48 H31 N5 = 677.25) 271 m / z = 676.82 (C49 H32 N4 = 676.26) 272 m / z = 676.82 (C49 H32 N4 = 676.26) 273 m / z = 753.90 (C54 H35 N5 = 753.28) 274 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 275 m / z = 601.71 (C42H27N5 = 601.22) 276 m / z = 570.63 (C39H27N2O5 = 570.18) 277 m / z = 827.99 (C60H37N5 = 827.30) 278 m / z = 904.08 (C66H41N5 = 903.33) 279 m / z = 904.08 (C66H41N5 = 903.33) 280 m / z = 827.00 (C61 H38 N4 = 826.31) 281 m / z = 903.10 (C67 H42 N4 = 902.32) 282 m / z = 903.10 (C67 H42 N4 = 902.23) 283 m / z = 817.95 (C 58 H 35 N 5 O = 817.28) 284 m / z = 793.97 (C 57 H 39 N 5 = 793.32) 285 m / z = 792.98 (C 58 H 40 N 4 = 792.32) 286 m / z = 792.98 (C 58 H 40 N 4 = 792.32) 287 m / z = 792.98 (C 58 H 40 N 4 = 792.32) 288 m / z = 702.82 (C49H30N6 = 702.25) 289 m / z = 701.83 (C50 H31 N5 = 701.25) 290 m / z = 701.83 (C50 H31 N5 = 701.25) 291 m / z = 701.83 (C50 H31 N5 = 701.25) 292 m / z = 778.91 (C 55 H 34 N 6 = 778.28) 293 m / z = 778.91 (C 55 H 34 N 6 = 778.28) 294 m / z = 777.93 (C56 H35 N5 = 777.28) 295 m / z = 777.93 (C56 H35 N5 = 777.28) 296 m / z = 854.02 (C62H39N5 = 853.32) 297 m / z = 777.93 (C56 H35 N5 = 777.28) 298 m / z = 853.04 (C 63 H 40 N 4 = 852.32) 299 m / z = 776.94 (C 57 H 36 N 4 = 776.29) 300 m / z = 830.00 (C60H39N5 = 829.32) 301 m / z = 829.01 (C61 H40 N4 = 828.32) 302 m / z = 880.06 (C64H41N5 = 879.33) 303 m / z = 879.07 (C65H42N4 = 878.34) 304 m / z = 880.06 (C64H41N5 = 879.33) 305 m / z = 878.05 (C 64 H 39 N 5 = 877.32) 306 m / z = 816.96 (C59 H36 N4 O = 816.28) 307 m / z = 893.06 (C65H40N4O = 829.32) 308 m / z = 894.05 (C 64 H 39 N 5 O = 893.31) 309 m / z = 601.71 (C42H27N5 = 601.22) 310 m / z = 600.72 (C43H28N4 = 600.23) 311 m / z = 600.72 (C43H28N4 = 600.23) 312 m / z = 677.81 (C48 H31 N5 = 677.25) 313 m / z = 752.92 (Cm55H36N4 = 752.29) 314 m / z = 752.92 (c 55 H 36 N 4 = 752.29) 315 m / z = 753.90 C (54H35N5 = 753.28) 316 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 317 m / z = 677.82 (C48 H31 N5 = 677.25) 318 m / z = 570.63 (C39H27N2O5 = 570.18) 319 m / z = 601.71 (C42H27N5 = 601.22) 320 m / z = 600.72 (C43H28N4 = 600.23) 321 m / z = 600.72 (C43H28N4 = 600.23) 322 m / z = 677.81 (C48 H31 N5 = 677.25) 323 m / z = 676.82 (C49 H32 N4 = 676.26) 324 m / z = 676.82 (C49 H32 N4 = 676.26) 325 m / z = 753.90 (C54 H35 N5 = 753.28) 326 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 327 m / z = 601.71 (C42H27N5 = 601.22) 328 m / z = 570.63 (C39H27N2O5 = 570.18) 329 m / z = 651.77 (C46 H29 N5 = 651.24) 330 m / z = 650.78 (C47H30N4 = 650.24) 331 m / z = 650.78 (C47H30N4 = 650.24). 332 m / z = 727.87 (C52 H33 N5 = 727.27) 333 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 334 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 335 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 336 m / z = 802.98 (C59H38N4 = 802.31) 337 m / z = 651.77 (C46 H29 N5 = 651.24) 338 m / z = 620.69 (C43H29N2O6 = 620.20) 339 m / z = 677.81 (C548 H31 N5 = 677.25) 340 m / z = 676.82 (C49 H32 N4 = 676.26) 341 m / z = 676.82 (C49 H32 N4 = 676.26) 342 m / z = 753.90 (C54 H35 N5 = 753.28) 343 m / z = 752.92 (C 55 H 36 N N 4 = 752.29) 344 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 345 m / z = 830.00 (C60H39N5 = 829.32) 346 m / z = 829.01 (C61 H40 N4 = 828.32) 347 m / z = 677.81 (C48 H31 N5 = 677.25) 348 m / z = 646.73 (C45H31N2OP = 646.21) 349 m / z = 601.71 (C42H27N5 = 601.22) 350 m / z = 600.72 (C43H28N4 = 600.23) 351 m / z = 600.72 (C43H28N4 = 600.23) 352 m / z = 677.81 (C48 H31 N5 = 677.25) 353 m / z = 676.82 (C49 H32 N4 = 676.26) 354 m / z = 676.82 (C49 H32 N4 = 676.26) 355 m / z = 753.90 (C54 H35 N5 = 753.28) 356 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 357 m / z = 601.71 (C42H27N5 = 601.22) 358 m / z = 599.73 (C44H29N3 = 599.23) 359 m / z = 599.73 (C44H29N3 = 599.23) 360 m / z = 570.63 (C39H27N2O5 = 570.18) 361 m / z = 651.77 (C46 H29 N5 = 651.24) 362 m / z = 650.78 (C47H30N4 = 650.24) 363 m / z = 650.78 (C47H30N4 = 650.24) 364 m / z = 651.77 (C46 H29 N5 = 651.24) 365 m / z = 650.78 (C 47 H 30 N 4 = 6050.24) 366 m / z = 650.78 (C47H30N4 = 650.24) 367 m / z = 651.77 (C46 H29 N5 = 651.24) 368 m / z = 650.78 (C47H30N4 = 650.24) 369 m / z = 650.78 (C47H30N4 = 650.24) 370 m / z = 548.64 (C39H24N4 = 548.20) 371 m / z = 624.74 (C45 H28 N4 = 624.23) 372 m / z = 624.74 (C45 H28 N4 = 624.23) 373 m / z = 700.84 (C51 H32 N4 = 700.26) 374 m / z = 700.84 (C51 H32 N4 = 700.26) 375 m / z = 760.94 (C58H36N2 = 760.28) 376 m / z = 760.94 (C58H36N2 = 760.28) 377 m / z = 811.00 (C62H38N2 = 810.30) 378 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 379 m / z = 853.90 (C54 H35 N5 = 753.28) 380 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 381 m / z = 752.92 (C 55 H 36 N 4 = 752.29) 382 m / z = 753.90 (C54 H35 N5 = 753.28) 383 m / z = 802.98 (C59H38N4 = 802.31) 384 m / z = 803.96 (C 58 H 37 N 5 = 803.30) 385 m / z = 677.81 (C48 H31 N5 = 677.25) 386 m / z = 725.89 (C54 H35 N3 = 725.28) 387 m / z = 725.89 (C54 H35 N3 = 725.28) 388 m / z = 725.85 (C52H31N5 = 725.25) 389 m / z = 726.88 (C 53 H 34 N 4 = 726.27) 390 m / z = 724.86 (C 53 H 32 N 4 = 724.26) 391 m / z = 827.99 (C60H37N5 = 827.30) 392 m / z = 827.00 (C61 H38 N4 = 826.31) 393 m / z = 827.00 (C61 H38 N4 = 826.31) 394 m / z = 854.02 (C62H39N5 = 853.32) 395 m / z = 853.04 (C 63 H 40 N 4 = 852.32) 396 m / z = 910.11 (C 64 H 39 N 5 S = 909.29) 397 m / z = 815.98 (C59 H37 N5 = 815.30) 398 m / z = 843.04 (C62H42N4 = 842.34) 399 m / z = 727.87 (C52 H33 N5 = 727.27) 400 m / z = 776.94 (C 57 H 36 N 4 = 776.29) 401 m / z = 650.78 (C47H30N4 = 650.24)

< Experimental Example  1> Fabrication of organic light emitting device

1) Fabrication of organic light emitting device

The transparent electrode ITO thin film obtained from the glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned for 5 minutes each using trichlorethylene, acetone, ethanol and distilled water sequentially, and stored in isopropanol before use.

Next, an ITO substrate was placed on a substrate folder of a vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine: 2-TNATA).

Subsequently, the chamber was evacuated until the degree of vacuum reached 10 -6 torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate.

N'-bis (? - naphthyl) -N, N'-diphenyl-4,4'-diamine (N, N'-diphenyl-4,4'-diamine: NPB) was added, and a current was applied to the cell to evaporate the hole transport layer to deposit a 300 Å thick hole transport layer.

After the hole injecting layer and the hole transporting layer were formed as described above, a blue light emitting material having the following structure was vapor-deposited as a light emitting layer thereon. Specifically, H1, a blue light emitting host material, was vacuum deposited on one cell in a vacuum vapor deposition apparatus to a thickness of 200 Å, and D1, a blue light emitting dopant material, was vacuum deposited by 5% on the host material.

Subsequently, one of the compounds shown in Table 15 below was deposited as an electron transporting layer to a thickness of 300 ANGSTROM.

Lithium fluoride (LiF) was deposited as an electron injection layer to a thickness of 10 Å, and an Al cathode was formed to a thickness of 1,000 Å to fabricate an OLED device.

On the other hand, all organic compounds required for OLED device fabrication were vacuum sublimated and refined at 10 ^-6 to 10 ^-8 torr for each material,

Table 15 shows the results of measuring the driving voltage, the luminous efficiency, the color coordinates (CIE), and the lifetime of the blue organic light emitting device manufactured according to the present invention.

compound Driving voltage
(V) Luminous efficiency
(cd / A) CIE
(x, y) life span
(T95) Comparative Example 1 E1 5.70 6.00 (0.134, 0.102) 20 Comparative Example 2 A 5.33 4.21 (0.134, 0.100) 12 Comparative Example 3 B 5.31 4.10 (0.134, 0.100) 8 Comparative Example 4 C 5.26 4.98 (0.134, 0.100) 9 Example 1 One 5.45 6.21 (0.134, 0.101) 37 Example 2 2 5.44 6.22 (0.134, 0.102) 34 Example 3 4 5.62 5.95 (0.134, 0.103) 42 Example 4 6 4.98 6.44 (0.134, 0.100) 40 Example 5 7 5.62 6.38 (0.134, 0.100) 35 Example 6 8 4.72 6.20 (0.134, 0.102) 48 Example 7 16 5.45 6.44 (0.134, 0.103) 33 Example 8 21 5.44 6.34 (0.134, 0.102) 36 Example 9 26 5.62 6.20 (0.134, 0.101) 39 Example 10 28 5.40 6.12 (0.134, 0.103) 44 Example 11 31 5.60 6.21 (0.134, 0.102) 43 Example 12 33 5.45 6.22 (0.134, 0.101) 37 Example 13 35 4.98 6.38 (0.134, 0.101) 42 Example 14 37 5.62 6.20 (0.134, 0.100) 45 Example 15 39 4.72 6.12 (0.134, 0.100) 43 Example 16 41 4.91 6.21 (0.134, 0.101) 41 Example 17 42 4.98 6.22 (0.134, 0.100) 40 Example 18 45 5.62 5.95 (0.134, 0.100) 33 Example 19 59 5.44 6.13 (0.134, 0.102) 25 Example 20 65 5.38 6.38 (0.134, 0.101) 39 Example 21 66 5.38 6.20 (0.134, 0.103) 40 Example 22 68 5.39 6.25 (0.134, 0.102) 41 Example 23 70 4.96 6.21 (0.134, 0.101) 37 Example 24 73 4.91 6.22 (0.134, 0.102) 33 Example 25 74 4.91 6.12 (0.134, 0.101) 42 Example 26 77 4.98 6.51 (0.134, 0.101) 39 Example 27 78 5.62 6.21 (0.134, 0.100) 41 Example 28 88 5.39 5.95 (0.134, 0.101) 34 Example 29 93 5.38 5.85 (0.134, 0.101) 35 Example 30 96 5.38 6.38 (0.134, 0.101) 39 Example 31 100 5.38 6.20 (0.134, 0.103) 40 Example 32 101 5.39 6.42 (0.134, 0.102) 43 Example 33 104 4.96 6.21 (0.134, 0.101) 37 Example 34 105 4.91 6.22 (0.134, 0.102) 33 Example 35 108 4.91 6.12 (0.134, 0.101) 37 Example 36 115 5.38 6.38 (0.134, 0.101) 39 Example 37 117 5.38 6.20 (0.134, 0.103) 40 Example 38 120 5.39 6.62 (0.134, 0.102) 43 Example 39 131 4.96 6.21 (0.134, 0.101) 37 Example 40 132 4.91 6.22 (0.134, 0.102) 33 Example 41 134 4.91 6.12 (0.134, 0.101) 42 Example 42 135 4.98 6.51 (0.134, 0.101) 39 Example 43 137 5.62 6.21 (0.134, 0.100) 41 Example 44 139 5.39 5.95 (0.134, 0.101) 34 Example 45 141 5.10 6.88 (0.134, 0.100) 41 Example 46 143 5.38 6.38 (0.134, 0.101) 39 Example 47 148 5.38 6.20 (0.134, 0.103) 40 Example 48 149 5.11 6.62 (0.134, 0.102) 43 Example 49 155 4.95 6.22 (0.134, 0.100) 41 Example 50 157 4.98 6.92 (0.134, 0.100) 40 Example 51 159 5.62 5.98 (0.134, 0.100) 39 Example 52 161 4.75 6.53 (0.134, 0.102) 40 Example 53 165 4.72 6.35 (0.134, 0.102) 42 Example 54 168 4.91 6.93 (0.134, 0.100) 45 Example 55 169 4.93 6.95 (0.134, 0.100) 40 Example 56 187 4.98 6.21 (0.134, 0.100) 40 Example 57 192 5.62 5.98 (0.134, 0.100) 34 Example 58 195 5.31 6.53 (0.134, 0.102) 35 Example 59 203 4.79 6.55 (0.134, 0.102) 48 Example 60 205 5.40 6.13 (0.134, 0.101) 39 Example 61 209 5.44 6.04 (0.134, 0.100) 41 Example 62 212 5.39 6.01 (0.134, 0.101) 34 Example 63 213 4.96 6.88 (0.134, 0.100) 45 Example 64 218 4.95 6.95 (0.134, 0.100) 41 Example 65 219 4.98 6.22 (0.134, 0.100) 40 Example 66 222 5.62 5.98 (0.134, 0.100) 33 Example 67 228 4.75 6.53 (0.134, 0.102) 40 Example 68 229 5.40 6.12 (0.134, 0.101) 39 Example 69 234 5.44 6.21 (0.134, 0.100) 41 Example 70 236 5.39 6.20 (0.134, 0.101) 36 Example 71 237 5.39 6.88 (0.134, 0.100) 45 Example 72 238 5.21 6.93 (0.134, 0.100) 43 Example 73 240 5.13 6.95 (0.134, 0.100) 41 Example 74 242 5.05 6.22 (0.134, 0.100) 40 Example 75 248 4.91 5.98 (0.134, 0.100) 33 Example 76 250 4.72 6.53 (0.134, 0.102) 48 Example 77 251 5.40 6.12 (0.134, 0.101) 39 Example 78 253 5.43 6.53 (0.134, 0.102) 48 Example 79 259 5.33 6.53 (0.134, 0.102) 48 Example 80 263 4.91 6.98 (0.134, 0.100) 43 Example 81 264 4.91 6.12 (0.134, 0.100) 35 Example 82 267 4.98 6.22 (0.134, 0.100) 40 Example 83 270 5.62 5.98 (0.134, 0.100) 38 Example 84 273 4.72 6.53 (0.134, 0.102) 48 Example 85 277 4.72 6.33 (0.134, 0.102) 41 Example 86 278 4.63 6.53 (0.134, 0.102) 48 Example 87 282 4.91 6.82 (0.134, 0.100) 43 Example 88 283 4.99 6.95 (0.134, 0.100) 41 Example 89 284 4.98 6.22 (0.134, 0.100) 40 Example 90 288 5.62 5.98 (0.134, 0.100) 33 Example 91 290 5.43 6.53 (0.134, 0.102) 41 Example 92 292 4.88 6.89 (0.134, 0.102) 42 Example 93 293 5.40 6.12 (0.134, 0.101) 39 Example 94 296 5.41 5.89 (0.134, 0.100) 41 Example 95 299 5.39 6.01 (0.134, 0.101) 32 Example 96 300 4.63 6.53 (0.134, 0.102) 48 Example 97 303 4.91 6.82 (0.134, 0.100) 43 Example 98 304 4.72 6.53 (0.134, 0.102) 38 Example 99 305 4.91 6.78 (0.134, 0.100) 43 Example 100 306 4.90 6.95 (0.134, 0.100) 41 Example 101 308 4.98 6.22 (0.134, 0.100) 40 Example 102 313 5.62 5.98 (0.134, 0.100) 33 Example 103 321 5.21 6.03 (0.134, 0.101) 33 Example 104 324 5.39 6.01 (0.134, 0.101) 32 Example 105 325 5.33 6.04 (0.134, 0.101) 33 Example 106 332 4.91 6.93 (0.134, 0.100) 43 Example 107 336 4.77 6.95 (0.134, 0.100) 41 Example 108 339 4.98 6.22 (0.134, 0.100) 40 Example 109 343 5.03 5.98 (0.134, 0.100) 39 Example 110 345 4.71 6.51 (0.134, 0.102) 41 Example 111 352 4.72 6.53 (0.134, 0.102) 48 Example 112 353 4.74 6.59 (0.134, 0.102) 45 Example 113 Synthesis of 363 5.42 6.13 (0.134, 0.101) 39 Example 114 365 4.72 6.53 (0.134, 0.102) 38 Example 115 367 4.91 6.78 (0.134, 0.100) 43 Example 116 370 5.44 5.89 (0.134, 0.100) 41 Example 117 372 5.36 6.01 (0.134, 0.101) 32 Example 118 373 4.96 6.82 (0.134, 0.100) 45 Example 119 374 4.91 6.93 (0.134, 0.100) 43 Example 120 376 4.95 6.95 (0.134, 0.100) 41 Example 121 379 5.34 6.11 (0.134, 0.101) 38 Example 122 380 4.86 6.76 (0.134, 0.100) 45 Example 123 381 4.94 6.73 (0.134, 0.102) 42 Example 124 382 4.91 6.55 (0.134, 0.100) 46 Example 125 384 5.31 6.29 (0.134, 0.100) 42 Example 126 388 5.22 6.11 (0.134, 0.100) 35 Example 127 391 5.33 6.24 (0.134, 0.102) 41 Example 128 395 5.31 6.57 (0.134, 0.102) 46 Example 129 396 4.72 6.53 (0.134, 0.102) 35 Example 130 397 4.79 6.55 (0.134, 0.102) 48 Example 131 398 5.40 6.13 (0.134, 0.101) 39 Example 132 399 5.12 5.89 (0.134, 0.100) 41 Example 133 400 5.31 6.01 (0.134, 0.101) 34 Example 134 401 5.11 6.88 (0.134, 0.100) 45

As can be seen from the results of Table 15, the organic light emitting device using the electron transporting layer material of the blue organic light emitting device of the present invention had a lower driving voltage, significantly improved luminous efficiency and life span as compared with Comparative Example 1.

In addition, it can be confirmed that the luminous efficiency and lifetime are superior to those of Comparative Examples 2 to 4. Particularly, the compounds B and C of Comparative Examples 3 and 4 were found to have one substituent group substituted for the core structure of the present invention. When the substituent group is substituted, the thermal stability is lower than that of the heterocyclic compound of the formula (1), and the lifetime is particularly lowered.

< Experimental Example  2> Fabrication of organic light emitting device

1) Fabrication of organic light emitting device

The transparent electrode ITO thin film obtained from the glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned for 5 minutes each using trichlorethylene, acetone, ethanol and distilled water sequentially, and stored in isopropanol before use.

Next, an ITO substrate was placed on a substrate folder of a vacuum deposition apparatus, and 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine: 2-TNATA).

Subsequently, the chamber was evacuated until the degree of vacuum reached 10 -6 torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer on the ITO substrate.

N'-bis (? - naphthyl) -N, N'-diphenyl-4,4'-diamine (N, N'-diphenyl-4,4'-diamine: NPB) was added, and a current was applied to the cell to evaporate the hole transport layer to deposit a 300 Å thick hole transport layer.

After the hole injecting layer and the hole transporting layer were formed as described above, a blue light emitting material having the following structure was vapor-deposited as a light emitting layer thereon. Specifically, H1, a blue light emitting host material, was vacuum deposited on one cell in a vacuum vapor deposition apparatus to a thickness of 200 Å, and D1, a blue light emitting dopant material, was vacuum deposited by 5% on the host material.

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

Lithium fluoride (LiF) was deposited as an electron injection layer to a thickness of 10 Å, and an Al cathode was formed to a thickness of 1,000 Å to fabricate an OLED device.

On the other hand, all organic compounds required for OLED device fabrication were vacuum sublimated and refined at 10 ^-6 to 10 ^-8 torr for each material,

In Experimental Example 2, the electron transport layer E1 was formed to a thickness of 250 ANGSTROM, and then a hole blocking layer was formed on the electron transport layer at a thickness of 50 ANGSTROM Thereby preparing an organic electroluminescent device.

Table 16 shows the results of measuring the driving voltage, the luminous efficiency, the color coordinates (CIE), and the lifetime of the blue organic light emitting device manufactured according to the present invention.

compound Driving voltage
(V) Luminous efficiency
(cd / A) CIE
(x, y) life span
(T95) Comparative Example 5 - 5.51 5.94 (0.134, 0.100) 31 Comparative Example 6 A 5.21 4.12 (0.134, 0.101) 12 Comparative Example 7 B 5.33 4.01 (0.134, 0.100) 11 Comparative Example 8 C 5.31 4.01 (0.134, 0.100) 11 Example 135 2 5.14 6.89 (0.134, 0.102) 54 Example 136 8 5.34 6.58 (0.134, 0.101) 44 Example 137 68 5.38 6.51 (0.134, 0.103) 47 Example 138 77 5.11 6.75 (0.134, 0.102) 46 Example 139 104 5.42 6.21 (0.134, 0.101) 54 Example 140 108 5.13 6.63 (0.134, 0.102) 52 Example 141 120 5.05 6.66 (0.134, 0.101) 49 Example 142 [ 205 5.42 6.13 (0.134, 0.101) 41 Example 143 212 5.14 6.89 (0.134, 0.102) 54 Example 144 213 5.34 6.58 (0.134, 0.101) 44 Example 145 273 5.38 6.51 (0.134, 0.103) 47 Example 146 277 5.11 6.75 (0.134, 0.102) 46 Example 147 288 5.32 6.25 (0.134, 0.101) 55 Example 148 388 5.14 6.46 (0.134, 0.102) 51 Example 149 391 5.04 6.62 (0.134, 0.101) 55 Example 150 395 5.32 6.25 (0.134, 0.101) 55

As can be seen from the results shown in Table 16, the organic light emitting device using the hole blocking layer material of the blue organic light emitting device of the present invention had a lower driving voltage, significantly improved luminous efficiency and lifetime, In addition, the luminous efficiency and lifetime were remarkably improved as compared with Comparative Examples 6 to 8. In particular, the compounds B and C of Comparative Examples 7 and 8 show that the core structure of the present invention is substituted with a substituent. When the substituent group is substituted, the thermal stability is lower than that of the heterocyclic compound of the formula (1), and the lifetime is particularly lowered.

The reason for this result is that the compound of Chemical Formula 1 is a bipolar type having both p-type and n-type, so that hole leakage can be prevented and excitons can be effectively confined in the light emitting layer.

< Experimental Example  3> Fabrication of organic light emitting device

1) Fabrication of organic light emitting device

The glass substrate coated with ITO thin film with a thickness of 1500Å was washed with distilled water ultrasonic waves. After the distilled water was washed, it was ultrasonically cleaned with a solvent such as acetone, methanol, isopropyl alcohol, dried, and UV-treated for 5 minutes using UV in a UV scrubber. Subsequently, the substrate was transferred to a plasma cleaner (PT), subjected to a plasma treatment for removing ITO work function and residual film in a vacuum state, and transferred to a thermal evaporation apparatus for organic vapor deposition.

An organic material was formed on the ITO transparent electrode (anode) in a two-stack WOLED (White Organic Light Device) structure. In the first stack, a hole transport layer was formed by thermally vacuum depositing TAPC to a thickness of 300 ANGSTROM. After forming a hole transporting layer, a light emitting layer was formed thereon by thermal vacuum deposition as follows. The light emitting layer was doped with TCp1 as a host with blue phosphorescent dopant FIrpic in an amount of 8% to deposit 300Å. The electron transporting layer was formed to a thickness of 400 ANGSTROM using TmPyPB, and doped with Cs ₂ CO ₃ to a compound shown in Table 17 below as a charge generation layer to form 100 Å.

In the second stack, first, MoO ₃ was thermally vacuum-deposited to a thickness of 50 Å to form a hole injection layer. A hole transport layer as a common layer was formed by doping TAPC with 20% MoO ₃ to form 100 Å, followed by deposition of TAPC to 300 Å. On the phosphorescent layer, dopant Ir (ppy) _3, which is a green phosphorescent dopant, And then 600 Å was formed using TmPyPB as an electron transport layer. Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 Å to form an electron injection layer. An aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200 Å to form a cathode Thereby preparing a light emitting device.

On the other hand, all the organic compounds required for OLED device fabrication were vacuum sublimated and refined under 10 ^-6 ~ 10 ^-8 torr for each material, and used for OLED fabrication.

The results of measuring the driving voltage, the luminous efficiency, the color coordinates (CIE), and the lifetime (T95) of the white organic light emitting device manufactured according to the present invention are shown in Table 17 below.

compound Driving voltage
(V) Luminous efficiency
(cd / A) CIE
(x, y) life span
(T95) Comparative Example 9 TmPyPB 8.57 57.61 (0.212, 0.433) 22 Comparative Example 10 BBQB 8.43 58.11 (0.220, 0.429) 22 Comparative Example 11 TBQB 8.47 58.90 (0.222, 0.430) 26 Comparative Example 12 A 7.21 41.11 (0.201, 0.398) 9 Comparative Example 13 B 7.28 41.12 (0.189, 0.388) 6 Comparative Example 14 C 7.22 41.01 (0.188, 0.388) 6 Example 1 One 7.24 61.88 (0.209, 0.415) 23 Example 2 33 6.98 60.58 (0.224, 0.429) 30 Example 3 66 6.89 72.10 (0.243, 0.442) 38 Example 4 78 6.71 69.65 (0.205, 0.411) 41 Example 5 101 6.49 71.44 (0.243, 0.442) 39 Example 6 152 7.34 58.29 (0.209, 0.419) 30 Example 7 156 7.21 59.33 (0.210, 0.420) 29 Example 8 157 7.44 69.65 (0.205, 0.411) 33 Example 9 158 7.41 71.44 (0.243, 0.442) 35 Example 10 296 6.95 58.29 (0.209, 0.419) 34 Example 11 299 7.21 59.33 (0.210, 0.420) 29 Example 12 370 6.71 69.65 (0.205, 0.411) 41 Example 13 372 6.49 71.44 (0.243, 0.442) 39 Example 14 373 6.95 58.29 (0.209, 0.419) 34

As can be seen from the results of Table 17, the organic light emitting device using the charge generating layer material of the two-stack white organic light emitting device of the present invention had a lower driving voltage and improved light emitting efficiency as compared with Comparative Examples 9 to 11 . The driving voltage was similar to that of Comparative Examples 12 to 14, but the luminous efficiency and lifetime were remarkably improved.

In particular, the compounds B and C of Comparative Examples 13 and 14 show that the core structure of the present invention is substituted with one substituent. When the substituent group is substituted, the thermal stability is lower than that of the heterocyclic compound of the formula (1), and the lifetime is particularly lowered.

100: substrate
200: anode
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 (15)

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

In Formula 1,
R ₂ to R ₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R &quot;; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group Or two or more groups adjacent to each other may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring,
R _a is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar ₁ is represented by - (L1) p- (Z1) q,
Ar ₂ is represented by - (L2) r- (Z2) s,
L1 and L2 are the same or different from each other and each independently represents a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Z1 and Z2 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted heterocycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; -SiRR'R &quot;; -P (= O) RR ', and an amine group substituted or unsubstituted with a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group And,
Wherein R, R 'and R "are the same or different from each other and each independently represents hydrogen, deuterium, -CN, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, Or an unsubstituted heteroaryl group,
p and r are integers of 1 to 4,
q and s are integers of 1 to 3,
n is an integer of 0 to 4; The term "substituted or unsubstituted" as used in claim 1 means a straight-chain or branched-chain alkyl of C1 to C60; C2 to C60 straight or branched chain alkenyl; Straight or branched chain alkynyl of C2 to C60; C3 to C60 monocyclic or polycyclic cycloalkyl; A C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; Wherein R is selected from the group consisting of C1 to C20 alkylamines, C6 to C60 mono- or polycyclic arylamines, and C2 to C60 mono- or polycyclic heteroarylamines. Means that at least two substituents selected from the above-exemplified substituents are substituted or unsubstituted with a substituent to which they are linked,
Wherein the definition of R, R 'and R "is the same as defined in the above formula (1). The method according to claim 1,
And R ₂ to R ₅ are the same or different and are each independently hydrogen or two or more groups adjacent to each other are bonded to each other to form a C 2 to C 40 aromatic hydrocarbon ring. The method according to claim 1,
L1 and L2 are the same or different from each other and are each independently C6 to C40 arylene; Or a C2 to C40 heteroarylene group,
Z1 and Z2 are the same or different from each other and each independently hydrogen; A substituted or unsubstituted C6 to C40 aryl group; A substituted or unsubstituted C2 to C40 heteroaryl group; Or P (= O) RR '
Wherein the definition of R and R 'is the same as defined in the above formula (1). The method according to claim 1,
Wherein R &lt; _{a &gt;} is hydrogen. The heterocyclic compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (2) to (9)
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above Chemical Formulas 2 to 9,
R _a, Ar ₁ , Ar ₂ , R ₂ to R ₅ and n are the same as defined in the above formula (1). The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the heterocyclic compound according to any one of claims 1 to 7 Lt; / RTI &gt; The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound. The organic light emitting device according to claim 8, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer comprises the heterocyclic compound. The organic light emitting device according to claim 8, wherein the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound. 10. The organic electroluminescent device of claim 8, wherein the organic light emitting device comprises a light emitting layer, a hole injecting layer, and a hole transporting layer. An electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. The organic electroluminescent device of claim 8, wherein the organic light emitting device comprises a first electrode, a first stack provided on the first electrode and including a first light emitting layer, a charge generating layer provided on the first stack, And a second electrode provided on the second stack, wherein the second electrode includes a second light emitting layer. 14. The organic light emitting device according to claim 13, wherein the charge generation layer comprises the heterocyclic compound. 14. The organic electroluminescent device according to claim 13, wherein the charge generation layer is an N-type charge generation layer, and the charge generation layer comprises the heterocyclic compound.

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