KR20170002208A - Hetero-cyclic compound and organic light emitting device using the same - Google Patents

Hetero-cyclic compound and organic light emitting device using the same Download PDF

Info

Publication number
KR20170002208A
KR20170002208A KR1020150092432A KR20150092432A KR20170002208A KR 20170002208 A KR20170002208 A KR 20170002208A KR 1020150092432 A KR1020150092432 A KR 1020150092432A KR 20150092432 A KR20150092432 A KR 20150092432A KR 20170002208 A KR20170002208 A KR 20170002208A
Authority
KR
South Korea
Prior art keywords
group
substituted
unsubstituted
monocyclic
polycyclic
Prior art date
Application number
KR1020150092432A
Other languages
Korean (ko)
Inventor
노영석
김기용
홍장미
최진석
최대혁
음성진
이주동
Original Assignee
희성소재 (주)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 희성소재 (주) filed Critical 희성소재 (주)
Priority to KR1020150092432A priority Critical patent/KR20170002208A/en
Publication of KR20170002208A publication Critical patent/KR20170002208A/en

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • C07D221/12—Phenanthridines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H01L51/50—
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention provides a hetero-cyclic compound capable of greatly improving lifespan, efficiency, electrochemical stability, and thermal stability of an organic light emitting device, and an organic light emitting device where the hetero-cyclic compound is contained in the organic compound layer. The hetero-cyclic compound is represented by chemical formula 1.

Description

HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME [0002]

The present invention relates to a heterocyclic compound and an organic light emitting device using 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

A compound having a chemical structure capable of satisfying the conditions required for a material usable in an organic light emitting device, for example, an appropriate energy level, electrochemical stability and thermal stability, The organic light-emitting device is required to be studied.

An embodiment of the present application provides a heterocyclic compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

Figure pat00001

In Formula 1,

At least one of X1 and X2 is N and the remainder is N or CR1,

At least one of R1 to R15 is - (L) p- (Y) q, and the others are the same or different, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C 1 to C 60 straight or branched alkyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkenyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkynyl group; A substituted or unsubstituted C 1 to C 60 straight or branched chain alkoxy group; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heterocycloalkyl group; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; -SiRR'R "; -P (= O) RR '; and C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups, or substituted or unsubstituted C 2 Or an amine group substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having a carbon number of 1 to 60 , or two or more adjacent groups of R1 to R15 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic or aromatic hydrocarbon ring Lt; / RTI >

L is a direct bond; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic arylene group; And a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroarylene group,

Y is hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C 1 to C 60 straight or branched alkyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkenyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkynyl group; A substituted or unsubstituted C 1 to C 60 straight or branched chain alkoxy group; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heterocycloalkyl group; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; -SiRR'R "; -P (= O) RR '; and C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups, or substituted or unsubstituted C 2 And an amine group substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having a carbon number of 1 to 60 ,

A substituted or unsubstituted C 1 to C 60 linear or branched alkyl group, a substituted or unsubstituted C 3 to C 60 linear or branched alkyl group, a substituted or unsubstituted C 3 to C alkenyl group, C 60 monocyclic or polycyclic cycloalkyl group; or a substituted or unsubstituted C 2 to monocyclic or polycyclic heteroaryl group of C 60 group, a; substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups,

p is an integer of 0 to 10, q is an integer of 1 to 10,

When two or more L and Y are present, they are each independently the same or different from each other.

Another embodiment of the present application is an organic light emitting device comprising a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers is a heterocyclic compound Emitting layer.

The heterocyclic compound according to one embodiment of the present application can be used as an organic material layer material of an organic light emitting device. The heterocyclic compound can be used as a material for a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer in an organic light emitting device. In particular, the heterocyclic compound represented by Formula 1 can be used as an electron transporting layer, a hole transporting layer, or a material of a light emitting layer of an organic light emitting device. In addition, when the compound is used in an organic light emitting device represented by Formula 1, 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 thermal stability of the compound.

FIGS. 1 to 3 schematically show a stacked structure of organic light emitting devices according to one embodiment of the present application.
Fig. 4 shows a graph of PL measurement at a wavelength of 230 nm of Compound 44. Fig.
5 shows a graph of the LTPL measurement of Compound 44 at a wavelength of 356 nm.
6 shows a PL measurement graph of Compound 53 at a wavelength of 269 nm.
7 is a graph showing the LTPL measurement of Compound 53 at a wavelength of 398 nm.
Fig. 8 shows a graph of PL measurement at a wavelength of 265 nm of Compound 55. Fig.
9 is a graph showing the LTPL measurement of Compound 55 at a wavelength of 376 nm.
DESCRIPTION OF THE REFERENCE NUMERALS
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

The present application will be described in detail below.

The heterocyclic compound according to one embodiment of the present application is characterized by being represented by the above formula (1). More specifically, the heterocyclic compound represented by the formula (1) can be used as an organic material layer material of the organic light emitting device according to the structural features of the core structure and the substituent.

According to one embodiment of the present application, the formula (1) may be represented by any one of the following formulas (2) to (4).

(2)

Figure pat00002

(3)

Figure pat00003

[Chemical Formula 4]

Figure pat00004

In the above Formulas 2 to 4, the definitions of R 1 to R 15 are the same as those in Formula 1.

In one embodiment of the present application, R1 to R15 in the above formula (1) are - (L) p- (Y) q and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C 1 to C 60 straight or branched alkyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkenyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkynyl group; A substituted or unsubstituted C 1 to C 60 straight or branched chain alkoxy group; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heterocycloalkyl group; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; -SiRR'R "; -P (= O) RR '; and C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups, or substituted or unsubstituted C 2 Or an amine group substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having a carbon number of 1 to 60. In this case, two or more adjacent groups of R2 to R15 may be bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic An aliphatic or aromatic hydrocarbon ring may be formed.

In one embodiment of the present application, among R1 to R15 in the above formula (1), R1 is - (L) p- (Y) q, and all others may be hydrogen.

In one embodiment of the present application, R1 in the formula (1) is - (L) p- (Y) q, L is a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic arylene group; And a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroarylene group, Y is a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; And substituted or unsubstituted C 1 to C 20 alkyl groups, substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups, or substituted or unsubstituted C 2 to C 60 mono- or polycyclic heteroaryl groups, Lt; / RTI > amine group.

In the present application, the substituents of the formulas (1) to (4) will be described in more detail as follows.

As used herein, the term "substituted or unsubstituted" A halogen group; -CN; A C 1 to C 60 straight or branched alkyl group; A C 2 to C 60 straight or branched chain alkenyl group; A C 2 to C 60 linear or branched alkynyl group; A C 3 to C 60 monocyclic or polycyclic cycloalkyl group; A C 2 to C 60 monocyclic or polycyclic heterocycloalkyl group; A C 6 to C 60 monocyclic or polycyclic aryl group; A C 2 to C 60 monocyclic or polycyclic heteroaryl group; -SiR ' R "; -P (= O) RR '; C 1 to C 20 alkylamine groups; A C 6 to C 60 monocyclic or polycyclic arylamine group; And a monocyclic or polycyclic heteroarylamine group having a carbon number of 2 to 60 , or substituted or unsubstituted with a substituent having two or more of the substituents bonded thereto, or two Quot; means that the above-mentioned substituent is substituted or unsubstituted with a connected substituent. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected. The additional substituents may be further substituted. A substituted or unsubstituted C 1 to C 60 linear or branched alkyl group, a substituted or unsubstituted C 3 to C alkyl group, a substituted or unsubstituted C 3 to C alkenyl group, a substituted or unsubstituted C 3 to C alkenyl group, to monocyclic or polycyclic cycloalkyl group of C 60; is a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; a substituted or unsubstituted monocyclic the unsubstituted C 6 to C 60 or polycyclic aryl group.

According to an exemplary embodiment of the present application, the "substituted or unsubstituted" is heavy hydrogen, a halogen group, SiRR'R ", P (= O ) RR ', C 1 to alkyl groups of linear or branched C 20, C 6 To C 60 monocyclic or polycyclic aryl groups, and C 2 to C 60 mono- or polycyclic heteroaryl groups,

Wherein R, R 'and R "are the same or different, each independently represent hydrogen, deuterium; deuterium, halogen group, C 1 to alkyl groups of linear or branched C 20, C 6 to monocyclic or polycyclic of C 60 An aryl group and a C 1 to C 60 straight or branched alkyl group substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having from 2 to 60 carbon atoms, a halogen, a C 1 to C 20 linear or branched A C 3 to C 60 monocyclic or polycyclic cycloalkyl group substituted or unsubstituted with an alkyl group, a C 6 to C 60 monocyclic or polycyclic aryl group, and a C 2 to C 60 monocyclic or polycyclic heteroaryl group, , C 1 to C 20 straight chain or an alkyl group branched-chain, C 6 to C 60 monocyclic or polycyclic aryl groups, and C 2 to C 60 monocyclic or polycyclic heteroaryl group is substituted or unsubstituted C 6 to C of the 60 monocyclic or polycyclic aryl group; or heavy, to Hagen, C 1 to C 20 straight chain or of the alkyl group of the branched, C 6 to C 60 monocyclic or polycyclic aryl groups, and C 2 to C 60 monocyclic or polycyclic heteroaryl group substituted or unsubstituted C 2 to the C 60 is a monocyclic or polycyclic heteroaryl group.

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

Figure pat00005
Figure pat00006
Figure pat00007
Figure pat00008
Figure pat00009
Figure pat00010
Figure pat00011

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.

According to one embodiment of the present application, Y in formula (1)

Figure pat00012
X3 and X4 are substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic aromatic heterocyclic ring.

remind

Figure pat00013
May be represented by any one of the following structural formulas, but it is not limited thereto.

Figure pat00014
Figure pat00015
Figure pat00016

Figure pat00017
Figure pat00018
Figure pat00019

In the above structural formulas, Z 1 to Z 3 are the same or different from each other and are each independently S or O,

Z < 4 > to Z < 9 > are the same or different from each other and each independently CR &

R 'and R "are the same or different and each independently hydrogen, substituted or unsubstituted C 1 to C 60 linear or branched alkyl, or substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic It is the aryl of the circle.

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

Figure pat00020

Figure pat00021

Figure pat00022

Figure pat00023

Figure pat00024

Figure pat00025

Figure pat00026

Figure pat00027

Figure pat00028

Figure pat00029

Figure pat00030

Figure pat00031

Figure pat00032

Figure pat00033

Figure pat00034

Figure pat00035

Figure pat00036

Figure pat00037

Figure pat00038

Figure pat00039

Figure pat00040

Figure pat00041

Figure pat00042

Figure pat00043

Figure pat00044

Figure pat00045

Figure pat00046

Figure pat00047

Figure pat00048

Figure pat00049

Figure pat00050

Figure pat00051

Figure pat00052

Figure pat00053

Figure pat00054

Figure pat00055

Figure pat00056

Figure pat00057

Figure pat00058

Figure pat00059

Also, by introducing various substituents into the structure of Formula 1, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

In addition, by introducing various substituents into the structure of Formula 1, it is possible to finely control the energy band gap, and the characteristics at the interface between the organic materials can be improved and the use of the materials can be diversified.

On the other hand, the above-mentioned heterocyclic compound has a high glass transition temperature (Tg) and thus 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.

Another embodiment of the present application provides an organic light emitting device comprising a heterocyclic compound represented by the above formula (1).

The organic light emitting device according to an embodiment of the present application can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described heterocyclic compound.

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.

Specifically, the organic light emitting device according to one embodiment of the present application includes a cathode, a cathode, and at least one organic layer provided between the anode and the cathode, and at least one of the organic layers includes a heterocycle ≪ / RTI >

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 light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers contains the heterocyclic compound represented by the formula (1).

The heterocyclic compound represented by the formula (1) may constitute one or more layers of the organic material layer of the organic light emitting device. However, if necessary, the organic material layer may be formed by mixing with other materials.

The heterocyclic compound represented by Formula 1 may be used as an electron transport layer, a hole blocking layer, a material for a light emitting layer, and the like in an organic light emitting device. For example, the heterocyclic compound represented by Formula 1 may be used as a material for an electron transport layer, a hole transport layer, or a light emitting layer of an organic light emitting device.

The heterocyclic compound represented by Formula 1 may be used as a material of the light emitting layer in an organic light emitting device. For example, the heterocyclic compound represented by Formula 1 may be used as a material of a phosphorescent host of an emission layer in an organic light emitting device.

In the organic light emitting device according to one embodiment of the present application, materials other than the heterocyclic compound of Formula 1 are illustrated below, but these are for illustrative purposes only and are not intended to limit the scope of the present application, , ≪ / 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-methyl compounds), poly [3,4- (ethylene-1,2-dioxy) compounds] (PEDT), 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. 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.

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.

< Example >

< Manufacturing example  1> Preparation of compound 1

Figure pat00060

1) Preparation of Compound 1-1

A round neck flask was charged with 2-bromotriphenylene (80 g, 260 mmol), 4,4,5,5-tetramethyl-2- (2-nitrophenyl) -1,3,2- Boro is (4,4,5,5-tetramethyl-2- (2 -nitrophenyl) -1,3,2-dioxaborolane, 70g, 286mmol), Pd (PPh 3) 4 (30g, 26mmol), CsF (70g , 520 mmol) of 1,4-dioxane (1,4-dioxane, 1,000 ml) was refluxed at 110 ° C for 2 h. Extract the mixture with MC and the organic layer was dried with MgSO 4. After concentrating, the product was separated by column chromatography (SiO 2 , Hexane: Dichloromethane = 1: 1) and precipitated with MC / MeOH to obtain Compound 1-1 (56 g, 61%).

2) Preparation of Compound 1-2

Under nitrogen, a round bottom flask was charged with Fe (44 g, 792 mmol) in a mixture of P-4 (56 g, 158.4 mmol) and EtOH (1,600 ml) and stirred for 10 min. AcOH (168 ml) was added thereto, and the mixture was refluxed at 80 ° C for 12 hours. After neutralization with NaHCO 3 at 0 ° C, the extracted organic layer was dried over MgSO 4 . Concentrated, dried with MgSO 4 , filtered and concentrated. The concentrate was subjected to MC / MeOH precipitation to give compound 1-2 (40 g, 86%).

3) Preparation of compound 1-3

Triethylamine (27 ml, 204 mmol) was added to a mixture of compound 1-2 (40 g, 136 mmol) and THF (1,000 ml) under nitrogen and the mixture was stirred for 10 minutes. A mixture of 4-bromobenzoyl chloride (57 ml, 409 mmol) in THF (100 ml) was added and stirred for 2 h. After distilled water was added, the mixture was extracted with MC, and the organic layer was dried with MgSO 4 . The organic layer was concentrated and then precipitated with MC / MeOH to give compound 1-3 (55.5 g, 85%).

4) Preparation of compound 1-4 (A)

POCl 3 (10 ml, 113 mmol) was added to a mixture of nitrobenzene (500 ml) of Compound 1-3 (54 g, 113.3 mmol) in a round bottom flask under nitrogen charging and the mixture was stirred at 150 ° C for 4 hours. The reaction was quenched with saturated aqueous NaHCO 3 solution at 0 ° C., extracted with MC, and MeOH was added to obtain compound 1-4 (B) (13.5 g, 24%). The filtrate was concentrated, and the crystals were collected by MeOH, and 10 g of the crystals were adsorbed to 1,000 ml of toluene at 110 ° C. The solid compound 1-4 (A) was obtained (31.6 g, 57%) by column chromatography (SiO 2 , Ethylacetate: Dichloromethane = 1:40).

5) Preparation of compound 1-5

(A) (7 g, 14.4 mmol), Pinacol Diboron (7.3 g, 28.9 mmol), PdCl 2 (dppf) (526 mg, 0.72 mmol), KOAc 4.2 g, 43.35 mmol) in 1,4-dioxane (1,4-dioxane, 70 ml) was refluxed at 120 ° C for 3 h. After extracting with MC, the organic layer was dried with MgSO 4 . After concentration, the solid material was subjected to MC / MeOH precipitation to give solid compound 1-5 (6.2 g, 80%).

6) Preparation of compound 1

(6.2 g, 11.66 mmol), 2-chloro-4,6-diphenyl-1,3 , 5-triazine, 3.1g, 11,66mmol ), Pd (PPh 3) 4 (1,4- dioxane (1,4 of 1.34g, 1.16mmol), K 2 CO 3 (3.2g, 23.3mmol) Dioxane, 100 ml) / H 2 O (20 ml) was stirred at 120 ° C for 10 hours. 120 ° C. The reaction mixture was filtered, washed with 110 ° C. 1,4-dioxane, and washed with MeOH to obtain Compound 1 (6.5 g, 87%).

< Manufacturing example  2> Preparation of compound 2

(2-chloro-4,6-diphenyl-1,3,5-triazine) instead of 2-chloro-4,6-diphenyl- 1-phenyl-1-phenyl-1H-benzo [d] imidazole instead of 2- (4-bromophenyl) To give the desired compound 2 (7.1 g, 80%).

< Manufacturing example  3> Preparation of Compound 3

(2-chloro-4,6-diphenyl-1,3,5-triazine) instead of 2-chloro-4,6-diphenyl- Phenyl) -1H-benzo [d] imidazole was used instead of 2-phenyl-lH-benzo [d] imidazole The desired compound 3 was obtained (6.9 g, 77%).

< Manufacturing example  4> Preparation of Compound 4

Compound (44) was prepared in the same manner as in the preparation of Compound 44 in Production Example 12, except for using Compound (1-4) (A) instead of Compound (44-2) to obtain Compound (4) (5.7 g, 41%).

< Manufacturing example  5> Preparation of Compound 7

(2-chloro-4,6-diphenyl-1,3,5-triazine) instead of 2-chloro-4,6-diphenyl- (7-chloro-2,6-diphenylpyrimidine) was used in place of 4-chloro-2-methylpyridine (7.3 g, 87%).

< Manufacturing example  6> Preparation of Compound 8

(2-chloro-4,6-diphenyl-1,3,5-triazine) instead of 2-chloro-4,6-diphenyl- (2-chloro-4,6-diphenylpyrimidine) was used instead of 2-chloro-4-fluoropyrimidine (7.4 g, 88%).

< Manufacturing example  7> Preparation of Compound 12

4 - ([1,1 (trifluoromethyl) phenyl] propane was used instead of 2-chloro-4,6-diphenyl-1,3,5- -Biphenyl] -4-yl) -2-bromoquinazoline) was used in place of 4-bromoquinazoline (4 - To give the desired compound 12 (8.1 g, 88%).

< Manufacturing example  8> Preparation of Compound 13

4 - ([1,1 (trifluoromethyl) phenyl] propane was used instead of 2-chloro-4,6-diphenyl-1,3,5- 4-yl) -6-chloro-2-phenylpyrimidine) was used instead of 4-chloro-2-phenylpyrimidine To give the desired compound 13 (7.9 g, 84%).

< Manufacturing example  9> Preparation of Compound 30

(2-chloro-4,6-diphenyl-1,3,5-triazine) instead of 2-chloro-4,6-diphenyl- (5-chloro-2,4,6-triphenylpyrimidine) was used instead of 6-triphenylpyrimidine (7.6 g, 81%).

< Manufacturing example  10> Preparation of Compound 442

(2-chloro-4,6-diphenyl-1,3,5-triazine) instead of 2-chloro-4,6-diphenyl- (4-bromophenyl) -2-phenylquinazoline was used in place of 4-bromo-2-phenylquinazoline to obtain the desired compound 442 (7.8 g, 83%).

< Manufacturing example  11> Preparation of Compound 31

Figure pat00061

1) Preparation of Compound A-1

(9,9-dimethyl-9H-fluoren-2-yl) boronic acid (25.9 g, 0.108 mol), 1 -bromo-2-nitrobenzene (1-bromo-2-nitrobenzene , 20g, 0.099mol), Pd (PPh 3) of 4 (5.7g, 4.95mmol), K 2 CO 3 (27.3g, 0.198mol) THF a mixture of (250ml) / H 2 O ( 50ml) was stirred under reflux for 24 hours. After the water layer was removed, the organic layer was dried with MgSO 4 . Column chromatography, concentrated (SiO 2, hexane: MC = 2: 1) to give a yellow solid separated as a compound A-1 (21g, 61% ).

2) Preparation of Compound A-2

To a round bottom flask under nitrogen, a mixture of o-DCB (300 ml) of compound A-1 (20 g, 0.0634 mmol) and PPh 3 (49.8 g, 0.190 mol) was refluxed for 18 hours. o-DCB was removed by vacuum distillation and then separated by column chromatography (SiO 2 , hexane: MC = 3: 1) to obtain a white solid compound A-2 (6.6 g, 36%

3) Preparation of Compound 31

Compound A-2 (5.26 g, 18.58 mmol), Cu (1 g, 1.85 mol) 18-crown-6-ether (18- (245 mg, 0.929 mmol) and K 2 CO 3 (5.1 g, 37.16 mmol) in o-DCB (200 ml) was stirred at reflux for 24 hours. The o-DCB was removed by distillation under reduced pressure and then the product was separated by column chromatography (SiO 2 , EA: MC = 1: 20) to obtain a solid compound 31 (7.5 g, 61%).

< Manufacturing example  12> Preparation of Compound 44

Figure pat00062

1) Preparation of compound 44-1

Triethylamine (27 ml, 204 mmol) was added to a mixture of compound 1-2 (40 g, 136 mmol) and THF (1,000 ml) under nitrogen and the mixture was stirred for 10 minutes. A mixture of 3-bromobenzoyl chloride (57 ml, 409 mmol) in THF (100 ml) was added and stirred for 3 h. After distilled water was added, the mixture was extracted with MC, and the organic layer was dried with MgSO 4 . After the organic layer was concentrated, MC was added, sonication was performed, and MeOH was added to obtain Compound 44-1 (54 g, 83%).

2) Preparation of compound 44-2 (A)

POCl 3 (10 ml, 113 mmol) was added to a mixture of nitrobenzene (500 ml) of compound 44-1 (54 g, 113.3 mmol) in a round bottom flask under nitrogen charging and the mixture was stirred at 150 ° C for 2 hours. The reaction was quenched with saturated aqueous NaHCO 3 solution at 0 ° C., extracted with MC, and MeOH was added to give compound 44-2 (B) (16 g, 29%). The filtrate was concentrated, and the crystals were collected by MeOH, and 10 g of the crystals were adsorbed to 1,000 ml of toluene at 110 ° C. Column chromatography (column chromatography, SiO 2, Ethylacetate : Dichloromethane = 1: 20) to obtain a separated solid compound 44-2 (A) (28g, 53 %).

3) Preparation of compound 44

Compound 44-2 (A) (11 g, 22.7 mmol) and NiCl 2 (352 mg, 2.72 mmol) were stirred in DMA with a round-bottomed round-bottomed flask. Ph 2 POEt (17.2 ml, 79.48 mmol) was added to the reaction, followed by stirring at 120 ° C for 24 hours. After the reaction, extracted with EA and dried with MgSO 4. The concentrate was adsorbed onto MC enriched solution and then separated by column chromatography (SiO 2 , MC: MeOH = 100: 1) to obtain a solid compound 44 (5.8 g, 42%).

< Manufacturing example  13> Preparation of Compound 53

Figure pat00063

1) Preparation of compound 53-1

(A) (7 g, 14.4 mmol), Pinacol Diboron (7.3 g, 28.9 mmol), PdCl 2 (dppf) (526 mg, 0.72 mmol), KOAc 4.2 g, 43.35 mmol) in 1,4-dioxane (1,4-dioxane, 70 ml) was refluxed at 120 ° C for 5 h. After extracting with MC, the organic layer was dried with MgSO 4 . After concentration, the solid material was subjected to MC / MeOH precipitation to give solid compound 53-1 (5.1 g, 67%).

2) Preparation of compound 53

To a round bottom flask was added compound 53-1 (6.4 g, 12 mmol), 4 - ([1,1'-biphenyl] 4- yl) -6- 1'-biphenyl] -4-yl) -6-bromo-2-phenylpyrimidine, 5.1g, 13.2mmol), Pd (PPh 3) 4 (1.38g, 1.2mmol), K 2 CO 3 (3.3g, 24mmol) Of 1,4-dioxane (120 ml) / H 2 O (30 ml) was stirred at 120 ° C for 12 hours. 120 ° C. The reaction mixture was filtered, washed with 1,4-dioxane at 110 ° C. and washed with MeOH to obtain Compound 53 (8 g, 94%).

< Manufacturing example  14> Preparation of Compound 41

(4 - ([1,1'-biphenyl] -4-yl) -6-bromo-2-phenylpyrimidine except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-2-phenylpyrimidine To give the desired compound 41 (8.2 g, 86%).

< Manufacturing example  15> Preparation of Compound 42

(4 - ([1,1'-biphenyl] -4-yl) -6-bromo-2-phenylpyrimidine (4-bromophenyl) -1-phenyl-1H-benzo [d] imidazole was used instead of 2- (4-bromophenyl) ), The target compound 42 was obtained (8.7 g, 87%).

< Manufacturing example  16> Preparation of Compound 43

(4 - ([1,1'-biphenyl] -4-yl) -6-bromo-2-phenylpyrimidine (4-bromophenyl) -2-phenyl-1H-benzo [d] imidazole was used instead of 1- (4-bromophenyl) ), The target compound 43 was obtained (8.2 g, 82%).

< Manufacturing example  17> Preparation of Compound 47

(4 - ([1,1'-biphenyl] -4-yl) -6-bromo-2-phenylpyrimidine (4-chloro-2,6-diphenylpyrimidine) was used instead of 4-chloro-2,6-diphenylpyrimidine instead of 4- bromo-2- (7.8 g, 82%).

< Manufacturing example  18> Preparation of Compound 48

(4 - ([1,1'-biphenyl] -4-yl) -6-bromo-2-phenylpyrimidine 2-chloro-4,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenylpyrimidine instead of 2- bromo-2- (7.1 g, 74%).

< Manufacturing example  19> Preparation of Compound 52

(4 - ([1,1'-biphenyl] -4-yl) -6-bromo-2-phenylpyrimidine 4-yl) -2-bromoquinazoline (4 - ([1,1'-biphenyl] -4-yl) -2 -bromoquinazoline), the target compound 52 was obtained (8.6 g, 84%).

< Manufacturing example  20> Preparation of Compound 451

(4 - ([1,1'-biphenyl] -4-yl) -6-bromo-2-phenylpyrimidine (4-bromophenyl) -2-phenylquinazoline was used instead of 4- (4-bromophenyl) -2-phenylpyrimidine instead of 4- To obtain the target compound 451 (7.6 g, 84%).

< Manufacturing example  21> Preparation of Compound 55

Figure pat00064

To a round bottom round bottom flask was added compound 44-2 (A) (8.5g, 17.6mmol), 2-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane- 2-yl) benzo [d] thiazole, 5.4 g, 16 mmol (0.14 mmol) (1,4-dioxane, 150 ml) / H 2 O (30 ml) of Pd (PPh 3 ) 4 (1.8 g, 1.6 mmol) and K 2 CO 3 (4.4 g, Was stirred at 120 &lt; 0 &gt; C for 12 h. 120 ° C The reaction mixture was filtered and washed with 1,4-dioxane at 110 ° C and washed with MeOH. After concentration, it was dissolved in hot toluene at 110 ° C and adsorbed. The solid was separated by column chromatography (SiO 2 , Ethylacetate: Dichloromethane = 1: 40) to obtain solid compound 55 (8.3 g, 76%).

< Manufacturing example  22> Preparation of Compound 72

Figure pat00065

Compound A-2 (5.97 g, 18.58 mmol), Cu (1 g, 1.85 mol) 18-crown-6-ether (18- DCB (200 ml) of K 2 CO 3 (5.1 g, 37.16 mmol) was refluxed with stirring for 24 hours. The o-DCB was removed by distillation under reduced pressure and then the product was separated by column chromatography (SiO 2 , HX: MC = 1: 1) to obtain a solid compound 72 (10 g, 74%).

< Manufacturing example  23> Preparation of Compound 87

Figure pat00066

1) Preparation of compound 87-1

(7 g, 14.4 mmol), Pinacol Diboron (7.3 g, 28.9 mmol), PdCl 2 (dppf) (526 mg, 0.72 mmol), KOAc 4.2 g, 43.35 mmol) in 1,4-dioxane (1,4-dioxane, 70 ml) was refluxed at 120 ° C for 5 h. After extracting with MC, the organic layer was dried with MgSO 4 . After concentration, the solid material was subjected to MC / HX precipitation to give solid compound 87-1 (7 g, 91%).

2) Preparation of compound 87

To a round bottomed round bottom flask was added compound 87-1 (7 g, 13.17 mmol), 4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline (4- of biphenyl] -4-yl) -2- bromoquinazoline, 4.7g, 13.17mmol), Pd (PPh 3) 4 (1.51g, 1.31mmol), K 2 CO 3 (3.6g, 26.3mmol) 1,4- di (1,4-dioxane, 100 ml) / H 2 O (20 ml) was stirred at 120 ° C for 5 h. 120 ° C. The reaction product was filtered, washed with 110 ° C. 1,4-dioxane, and washed with MeOH to obtain Compound 87 (7.6 g, 84%).

< Manufacturing example  24> Preparation of Compound 76

4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline The same as the preparation of 87 except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl- To give the desired compound 76 (7.9 g, 83%).

< Manufacturing example  25> Preparation of Compound 77

4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline Except that 2- (4-bromophenyl) -1-phenyl-1H-benzo [d] imidazole was used instead of 2- (4-bromophenyl) 87, the desired compound 77 was obtained (8.2 g, 81%).

< Manufacturing example  26> Preparation of Compound 79

(4.2 g, 42%) was prepared in the same manner as in the preparation of Compound 44 in Production Example 12, except that Compound 1-4 (b) was used in place of Compound 44-2 (A).

< Manufacturing example  27> Preparation of Compound 82

4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline The objective compound 82 was obtained in the same manner as in the preparation of the compound 87 except that 4-chloro-2,6-diphenylpyrimidine was used instead of 4-chloro-2,6-diphenylpyrimidine (7.5 g, 78% ).

< Manufacturing example  28> Preparation of Compound 83

4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline (7.2 g, 75%) was obtained in the same manner as in the preparation of Compound 87 except that 2-chloro-4,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenylpyrimidine instead of 2- ).

< Manufacturing example  29> Preparation of Compound 88

4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline Instead of 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyrimidine 2-phenylpyrimidine), the target compound 88 was obtained (8.1 g, 76%).

< Manufacturing example  30> Preparation of Compound 101

Figure pat00067

1) Preparation of Compound 101-1

Triethylamine (14.3 ml, 102 mmol) was added to a mixture of compound 1-2 (10 g, 34 mmol) and THF (100 ml) under nitrogen and then stirred for 10 minutes. A mixture of 2-naphthoyl chloride (7.1 g, 37.4 mmol) in THF (10 ml) was added at 0 ° C, followed by stirring for 2 hours. After distilled water was added, the mixture was extracted with MC, and the organic layer was dried with MgSO 4 . The organic layer was concentrated and then subjected to column chromatography (SiO 2 , HX: Dichloromethane = 1: 1) to obtain solid compound 101-1 (15, 93%).

2) Preparation of compound 101

POCl 3 (2.95 ml, 31.6 mmol) was added to a mixture of nitrobenzene (150 ml) of compound 101-1 (15 g, 31.6 mmol) in a round bottom flask under nitrogen charging and the mixture was stirred at 150 ° C for 12 hours. The reaction was quenched with saturated aqueous NaHCO 3 solution at 0 ° C, extracted with MC, concentrated, and then nitrobenzene was removed. The solid compound 101 was obtained (6.2, 43%) by column chromatography (SiO 2 , HX: Dichloromethane = 1: 3) after boiling at 1,000 ° C. in 1,000 ml of toluene.

< Manufacturing example  31> Preparation of Compound 116

Figure pat00068

1) Preparation of compound 116-1

Was prepared in the same manner as in the preparation of the compound 87-1 in Production Example 23 except that the compound 44-2 was used instead of the compound 1-4 (b) to obtain the desired compound 116-1 (28 g, 85%).

2) Preparation of compound 116

The target compound 116 was obtained (7.8 g, 82%) in the same manner as in the production of the compound 76 in Production Example 24, except that the compound 116-1 was used instead of the compound 87-1.

< Manufacturing example  32> Preparation of Compound 117

The target compound 117 was obtained (7.7 g, 76%) in the same manner as in the production of the compound 77 in Production Example 25, except that the compound 116-1 was used instead of the compound 87-1.

< Manufacturing example  33> Preparation of Compound 119

The compound 119 was obtained in the same manner as in the preparation of the compound 44 in Production Example 12 except that the compound 44-2 (b) was used in place of the compound 44-2 (A) (4.3 g, 43%).

< Manufacturing example  34> Preparation of Compound 122

The target compound 122 was obtained (7.9 g, 83%) in the same manner as in the preparation of the compound 82 in Production Example 27, except that the compound 116-1 was used instead of the compound 87-1.

< Manufacturing example  Preparation of Compound 123

The target compound 123 was obtained (8.2 g, 86%) in the same manner as in the preparation of the compound 83 in Production Example 28, except that the compound 116-1 was used instead of the compound 87-1.

< Manufacturing example  Preparation of Compound 127

The objective compound 127 was obtained (8.1 g, 85%) in the same manner as in the preparation of the compound 87 in Production Example 23, except that the compound 116-1 was used instead of the compound 87-1.

< Manufacturing example  Preparation of Compound 128

The target compound 128 was obtained (8.3 g, 87%) in the same manner as in the production of the compound 88 in Production Example 29, except that the compound 116-1 was used instead of the compound 87-1.

< Manufacturing example  Preparation of Compound 138

Figure pat00069

9 mL (22.7 mmol) of 2.5 M n-BuLi was added dropwise to a mixed solution of 10 g (20.64 mmol) of Compound 44-2 (B) and 100 mL of THF at -78 ° C and stirred for 30 minutes. 7.83 g (30.96 mmol) of chlorotriphenylsilane was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was extracted with distilled water at room temperature. The organic layer was dried over MgSO 4 and concentrated. The concentrate was separated by column chromatography (SiO 2 , EA: MC = 1: 30) to obtain solid compound 138 (8.3, 60%).

< Manufacturing example  Preparation of Compound 157

Figure pat00070

1) Preparation of compound 157-1

A round neck bottom flask was charged with 4,4,5,5-tetramethyl-2- (triphenylene-1-yl) -1,3,2-dioxabororane (4,4,5,5- (2-bromoaniline, 24 g, 141 mmol), Pd (PPh 3 ) 4 (8.1 g, 7.05 mmol) was added to a solution of 2- (triphenylen-1-yl) -1,3,2- dioxaborolane ) And K 3 PO 4 (89.7 g, 424 mmol) in 1,4-dioxane (800 ml) / H 2 O (200 ml) was refluxed at 110 ° C for 12 h. Extract the mixture with MC and the organic layer was dried with MgSO 4. Filter, concentrated on silica gel (Silicagel filter) by column chromatography (column chromatography, SiO 2, Hexane : Dichloromethane = 1: 1) and separated by gave Compound 157-1 (40g, 88%).

2) Preparation of compound 157-2

Triethylamine (19 ml, 137.5 mmol) was added to a mixture of compound 157-1 (40 g, 125 mmol) and THF (500 ml) under nitrogen and the mixture was stirred for 10 minutes. A mixture of 4-bromobenzoyl chloride (32 g, 150 mmol) in THF (50 ml) was added and stirred for 3 h. After extraction with MC, the organic layer was dried with MgSO 4 . The organic layer was concentrated, adsorbed, and separated by column chromatography (SiO 2 , Hexane: Dichloromethane = 1: 3) to obtain solid compound 157-2 (55 g, 87%).

3) Preparation of compound 157-3

POCl 3 (5 ml, 54.5 mmol) was added to a mixture of nitrobenzene (700 ml) of compound 157-2 (55 g, 109 mmol) in a round bottom flask under nitrogen charging and the mixture was stirred at 150 ° C for 4 hours. The reaction was quenched with saturated aqueous NaHCO 3 solution at 0 ° C and then extracted with MC and the organic layer was dried over MgSO 4 . After concentration, the product was separated by column chromatography (SiO 2 , Hexane: Dichloromethane = 3: 1) to obtain a solid compound 157-3 (42 g, 80%).

4) Preparation of compound 157-4

(10 g, 20.6 mmol), Pinacol Diboron (10.4 g, 41.2 mmol), PdCl 2 (dppf) (753 mg, 1.03 mmol), KOAc (6 g, 61.8 mmol) of 1,4-dioxane (1,4-dioxane, 100 ml) was refluxed at 120 ° C for 5 h. After extracting with MC, the organic layer was dried with MgSO 4 . Column chromatography, concentrated (column chromatography, (SiO 2, Hexane: Dichloromethane = 5: 1, by separating them) to obtain a solid compound 157-4 (9g, 82%).

5) Preparation of compound 157

Wonnek compound to a round bottom flask 157-4 (8g, 15mmol), 4- bromo-2,6-diphenyl-pyrimidine (4-bromo-2,6-diphenylpyrimidine , 4.6g, 15.49mmol), Pd (PPh 3 ) 4 (1.7 g, 1.5 mmol) and K 2 CO 3 (4.1 g, 30 mmol) in 1,4-dioxane (150 ml) / H 2 O (30 ml) Lt; / RTI &gt; 120 ° C. The reaction product was filtered, washed with 110 ° C. 1,4-dioxane, and washed with MeOH to obtain Compound 157 (8.4 g, 88%).

< Manufacturing example  40> Preparation of Compound 185

Figure pat00071

1) Preparation of compound B-1

Ethanol (1,000 ml) of 1,2-dicyclohexanone (30.0 g, 0.374 mol) and phenylhydrazine hydrochloride (77.37 g, 0.749 mol) was added to a round bottom flask under nitrogen, Sulfuric acid (1.4 mL, 0.0374 mol) was slowly added dropwise to the mixture, followed by stirring at 60 ° C for 4 hours. The solution cooled to room temperature was filtered to give a tan solid (69 g, 93%).

Trifluoroacetic acid (46.5 mL, 0.6 mol) was added to a mixture of the above solid (68.9 g, 0.25 mol) and acetic acid (700 mL) in a round-bottomed flask with a round neck and stirred at 100 ° C for 12 hours. The solution cooled to room temperature was washed with acetic acid and hexane and filtered to obtain an ivory solid compound B-1 (27.3 g, 42%).

2) Preparation of compound B-2

(2.1 g, 0.0082 mol), iodobenzene (2.5 g, 0.013 mol), Cu (0.312 g, 0.0049 mol), 18-crown-6-ether -crown-6-ether, 0.433 g, 0.0016 mol) and K 2 CO 3 (3.397 g, 0.0246 mol) in 20 mL of dioxane was refluxed for 12 hours. The solution cooled to room temperature was extracted with MC / H 2 O, concentrated, and separated by column chromatography (SiO 2 , hexane: Ethyl acetate = 10: 1) to obtain a white solid compound B-2 (1.76 g, 64%).

3) Preparation of compound 185

(6.1 g, 18.5 mmol), Cu (1.2 g, 18.5 mol), 18-crown-6-ether (9 g, 18.5 mmol) were added to a round bottomed round bottom flask under nitrogen. 6-ether, 244 mg, 0.92 mmol) and K 2 CO 3 (5.1 g, 37 mmol) in o-DCB (150 ml) was refluxed for 24 hours. The o-DCB was removed by distillation under reduced pressure, and then separated by column chromatography (SiO 2 , EA: MC = 1: 40) to obtain a solid compound 185 (8.6 g, 63%).

< Manufacturing example  Preparation of Compound 11

(2-chloro-4,6-diphenyl-1,3,5-triazine) instead of 2-chloro-4,6-diphenyl- 9-bromophenanthrene), the desired compound 11 was obtained (7.1 g, 65%).

< Manufacturing example  42> Preparation of Compound 19

The same procedure as in Production Example 1 was repeated except that 4-bromodibenzo [b, 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6- , d] thiophene was used instead of 4-bromodibenzo [b, d] thiophene to obtain the desired compound 19 (9.1 g, 82%).

< Manufacturing example  43> Preparation of Compound 23

The target compound 23 was obtained (8.4 g, 61%) in the same manner as in the preparation of the compound 138 except that in the Production Example 38, Compound (a) was used instead of Compound 44-2 (b).

< Manufacturing example  Preparation of Compound 246

(4 - ((2-chloro-4,6-diphenyl-1,3,5-triazine) 4-yl) phenanthro [9,10-i] phenanthridine (9,9-diphenyl- (4 '- (4,6-diphenyl-1,3,5-triazin-2-yl) - [1,1'-biphenyl] -4-yl) phenanthro [9,10-i] phenanthridine , The target compound 246 was obtained (10.2 g, 76%).

< Manufacturing example  45> Preparation of Compound 97

(4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline was obtained in the same manner as in Production Example 23, The objective Compound 97 was obtained (8.9 g, 78%) in the same manner as in the preparation of Compound 87, except that 1-bromopyrene was used instead.

< Manufacturing example  46> Preparation of Compound 534

(4 - ([1,1'-biphenyl] -4-yl) -2-bromoquinazoline was obtained in the same manner as in Production Example 23, Instead of 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine, 2- (4-bromophenyl) The target compound 534 was obtained (10.4 g, 77%) in the same manner as in the preparation of the compound 87 except that the compound 87 was used.

< Manufacturing example  Preparation of Compound 169

4-bromodibenzo [b, d] thiophene was used instead of 4-bromo-2,6-diphenylpyrimidine in Production Example 39. [ thiophene) was used instead of (4-fluorophenyl) thiophene, the target compound 169 was obtained (9.6 g, 87%).

< Manufacturing example  Preparation of Compound 172

The title compound was prepared analogously to Preparation 39 except that 1-bromopyrene was used instead of 4-bromo-2,6-diphenylpyrimidine in Production Example 39 and The target compound 172 was obtained (7.5 g, 66%).

< Manufacturing example  Preparation of Compound 173

In the same manner as in the preparation of Compound 138 except that 157-3 was used instead of 44-2 (B) in Production Example 38, desired Compound 173 was obtained (7.4 g, 54%).

< Manufacturing example  50> Preparation of Compound 188

In the same manner as in Production Example 22, except that 44-2 (A) and 157-3 (biphenyl) -4-yl) amine were used in place of di [(1,1'- , N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- -9,9-dimethyl-9H-fluoren-2-amine), the desired compound 188 was obtained (12.1 g, 77%).

< Manufacturing example  Preparation of Compound 18

4-bromodibenzo [b, d] furan instead of 4-bromodibenzo [b, d] thiophene in Production Example 42, , The target compound 18 was obtained (8.2 g, 76%).

< Manufacturing example  52> Preparation of Compound 20

Bromo-9-phenyl-9H-carbazole instead of 4-bromodibenzo [b, d] thiophene in Production Example 42. [ 9H-carbazole), the desired compound 20 was obtained (9.6 g, 78%).

< Manufacturing example  Preparation of Compound 153

The compound 153 was obtained in the same manner as in the preparation of the compound 3, except that 157-4 was used instead of 1-5 in Production Example 3 to obtain the objective compound 153 (8.8 g, 69%).

The compounds were prepared in the same manner as in the above Preparation Examples, and the results of the confirmation of the synthesis were shown in Tables 1 and 2. Table 1 shows the measured values of 1 H NMR (CDCl 3 , 200 Mz) and Table 2 shows the measured values of FD-MS (field desorption mass spectrometry).

compound 1 H NMR (CDCl 3, 200Mz ) One d), 8.08 (2H, d), 8.28 (4H, d), 8.12 (3H, d), 8.06 m), 7.60-7.41 (7H, m) 2 d), 7.98 (1H, d), 7.88-7.78 (10H, d), 8.08 m), 7.60-7.45 (7H, m), 7.25-7.22 (4H, m) 3 (1H, d), 8.08 (2H, d), 8.08 (2H, d) , 7.88-7.78 (10H, m), 7.68-7.41 (7H, m), 7.22 (2H, m) 4 (1H, m), 7.60 (1H, d), 8.09 (2H, d) t), 7.45 (6 H, m) 7 (8H, m), 7.60-7.41 (7H, m), 8.12-7.98 (2H, ) 8 d), 7.98 (1H, d), 7.88-7.79 (12H, d), 8.04 m), 7.60-7.41 (7H, m) 12 (1H, d), 8.81 (2H, d), 8.30 (2H, d), 8.16-8.06 (5H, m), 7.98 7.41 (7 H, m) 13 (2H, d), 8.81 (2H, d), 8.33-8.28 (7H, m), 8.12-8.6 (4H, m), 7.98 m), 7.60-7.41 (9H, m) 30 d), 7.98 (1H, d), 7.88-7.79 (10H, d), 8.08 (2H, d) m), 7.60-7.41 (10H, m), 7.28 (2H, d) 31 (1H, d), 8.85 (1H, s), 8.30 (2H, d), 8.12 to 8.06 (6H, m), 7.98 7.44 (6H, m), 7.29 ~ 7.24 (2H, m), 1.72 (6H, m) 41 (8H, m), 7.98 (1H, d), 7.88-7.78 (6H, m), 7.60-7.41 (8H, m) ) 42 d), 7.98 (1H, d), 8.21 (1H, s), 8.12 (3H, d), 8.06 , 7.88-7.78 (8H, m), 7.60-7.45 (9H, m), 7.25-7.22 (4H, m) 43 (1H, d), 7.98 (1H, d), 7.88 (1H, 8H, m), 7.68-7.41 (9H, m), 7.22 (2H, m) 44 (2H, d), 7.82 (1H, m), 7.61-7.45 (8H, m) 47 d), 7.98 (1H, d), 7.88-7. 78 (9H, m), 7.60 (1H, 7.41 (8 H, m) 48 d), 7.98 (1H, d), 7.88-7.78 (10H, m), 7.60 (1H, d) 7.41 (8 H, m) 52 m), 7.60-7.41 (8H, m), 7.98 (1H, d) 53 (9H, m), 7.60-7.41 (10H, m), 7.98 (2H, d), 8.30 ) 55 (8H, m), 7.60-7.41 (6H, m), 8.12-7.98 (2H, ) 72 d), 7.98 (1H, d), 7.88-7.78 (6H, m), 7.60-7.41 (18H, m), 6.69 6.65 (5H, m) 76 (1H, d), 7.88 (1H, m), 7.81 (2H, d) 7.41 (7 H, m) 77 (9H, m), 7.60 (1H, m), 8.48 (3H, m) 7.45 (7 H, m), 7.25-7.22 (4 H, m) 79 (1H, m), 7.60 (1H, t), 7.45 (1H, 6H, m) 82 (7H, m), 7.60-7.41 (7H, m), 8.12-7.98 (5H, m) ) 83 (1H, d), 7.60 (1H, m), 7.81 (1H, d) 7.41 (7 H, m) 87 (1H, d), 7.80 (1H, d), 7.90 (1H, m) 7.41 (7 H, m) 88 (1H, d), 7.60 (1H, m), 7.81 (1H, d) 7.41 (7 H, m) 101 m, 8.38 (1H, d), 8.12-7.78 (13H, m), 7.60-7.59 (3H, m) 116 (8H, m), 7.98 (1H, d), 7.88-7.82 (5H, m), 7.60-7.41 (8H, m) ) 117 (2H, m), 8.12 to 8.06 (4H, m), 7.98 (1H, d), 7.88 to 7.78 (7H, m) 7.60-7.45 (9H, m), 7.25-7.22 (4H, m) 119 (8H, m), 7.60 (1H, d), 7.98 (1H, 122 (8H, m), 7.60-7.41 (8H, m), 8.08-8.81 (5H, m) ) 123 (9H, m), 7.60-7.41 (8H, m), 7.98 (1H, ) 127 (9H, m), 7.60-7.41 (9H, m), 7.98 (1H, 128 (2H, d), 8.81 (2H, d), 8.30-8.28 (4H, m), 8.16-8.06 (5H, m), 7.98 7.60 ~ 7.51 (4H, m) 138 (1H, d), 7.98 (1H, d), 7.98 (1H, 7.37 (18 H, m) 157 (2H, d), 8.81 (2H, d), 8.33-8.28 (4H, m), 8.12-7.98 (5H, m), 7.88-7.78 (8H, m), 7.60-7.41 ) 185 (2H, d), 8.30 (2H, d), 8.12-7.71 (16H, m), 7.60-7.45 (7H, m), 7.33-7.25 442 (2H, d), 8.81 (2H, d), 8.30-8.28 (4H, m), 8.16-8.06 (5H, m), 7.98 7.60 ~ 7.51 (4H, m) 451 (2H, d), 8.28 (2H, d), 8.16-8.06 (5H, m), 7.98 (1H, d), 7.88-7.70 7.41 (7 H, m) 11 m), 7.60 (1H, t), 7.28 (2H, d), 8.81 (2H, d) 19 m), 7.28 (2H, d), 8.80 (2H, d), 8.80 23 m), 7.60-7.37 (18H, m), 7.98 (1H, d), 8.46 246 (1H, d), 8.81 (2H, d), 8.28 (4H, d), 8.12 to 8.06 (4H, m), 7.98 7.41 (7 H, m), 7.25 (2 H, d) 97 (7H, m), 8.12 to 8.06 (4H, m), 7.98 (1H, d), 7.88 to 7.78 7.60-7.41 (9H, m) 534 (9H, m), 7.60 (1H, d), 8.08 (2H, d) 7.41 (7 H, m), 7.25 (2 H, d) 169 m), 7.28 (2H, m), 8.30 (2H, d), 8.81 (2H, d), 8.45-8.41 172 (2H, d), 8.81 (2H, d), 8.18-7.98 (8H, m), 7.88-7.71 (12H, m), 7.60 173 m), 7.60-7.37 (18H, m), 7.98 (2H, d), 8.40 188 m), 7.60-7.38 (11H, m), 7.28 (1H, t), 6.72-6.69 (5H, m) ), 6.58 (1H, d), 1.72 (6H, s) 18 (2H, m), 7.38-7.28 (5H, m), 8.89 (2H, ) 20 (2H, m), 7.25-7.33 (2H, m), 8.12-7.88 (16H, m) 153 (2H, d), 8.81 (2H, d), 8.56 (1H, m), 8.28 (2H, m), 8.12 to 8.06 (4H, m), 7.98 10H, m), 7.68-7.41 (7H, m), 7.22 (2H, m)

compound FD-Mass compound FD-Mass One m / z = 636.74 (C46H28N4 = 63623) 2 m / z = 673.80 (C50 H31 N3 = 673.25) 3 m / z = 673.80 (C50 H31 N3 = 673.25) 4 m / z = 605.66 (C43H28NOP = 605.19) 5 m / z = 532.63 (C40H24N2 = 532.19) 6 m / z = 532.63 (C40H24N2 = 532.19) 7 m / z = 635.75 (C 47 H 29 N 3 = 635.75) 8 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 9 m / z = 811.97 (C61 H37 N3 = 811.30) 10 m / z = 682.81 (C52H30N2 = 682.24) 11 m / z = 581.70 (C45 H27 N = 581.21) 12 m / z = 685.81 (C51 H31 N3 = 685.25) 13 m / z = 711.85 (C53H33N3 = 711.27) 14 m / z = 657.80 (51C31HN = 657.25) 15 m / z = 614.76 (C44H26N2S = 614.18) 16 m / z = 614.76 (C44H26N2 = 614.18) 17 m / z = 625.72 (C45H27N3O = 625.72) 18 m / z = 571.66 (C43H25NO = 571.19) 19 m / z = 587.73 (C43H25NS = 587.17) 20 m / z = 646.78 (C49H30N2 = 646.24) 21 m / z = 631.76 (C49H29N = 631.23) 22 m / z = 605.72 (C 47 H 27 N = 605.21) 23 m / z = 663.88 (C49H33NSi = 663.24) 24 m / z = 737.96 (C 55 H 35 NSi = 737.25) 25 m / z = 597.75 (C46 H31 N = 597.25) 26 m / z = 455.55 (C35H21N = 455.17) 27 m / z = 405.49 (C31 H19 N = 405.15) 28 m / z = 455.55 (C35H21N = 455.17) 29 m / z = 721.88 (C56 H35 N = 721.28) 30 m / z = 711.85 (C53H33N3 = 711.27) 31 m / z = 686.84 (C52H34N2 = 686.27) 32 m / z = 676.83 (C49H28N2S = 676.20) 33 m / z = 660.76 (C49H28N2O = 660.22) 34 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 35 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 36 m / z = 570.68 (C43H26N2 = 570.21) 37 m / z = 724.89 (C 55 H 36 N 2 = 724.29) 38 m / z = 764.95 (C 58 H 40 N 2 = 764.32) 39 m / z = 646.789 (C49H30N2 = 646.24) 40 m / z = 800.98 (C61 H40 N2 = 800.32) 41 m / z = 636.74 (C46H28N4 = 636.23) 42 m / z = 673.80 (C50 H31 N3 = 673.25) 43 m / z = 673.80 (C40H31N3 = 673.25) 44 m / z = 605.66 (C43H28NOP = 605.19) 45 m / z = 532.63 (C40H24N2 = 532.19) 46 m / z = 532.63 (C40H24N2 = 532.19) 47 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 48 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 49 m / z = 811.97 (C61 H37 N3 = 811.30) 50 m / z = 682.81 (C52H30N2 = 682.24) 51 m / z = 581.70 (C45 H27 N = 581.21) 52 m / z = 685.81 (C51 H31 N3 = 685.25) 53 m / z = 711.85 (C53H33N3 = 711.27) 54 m / z = 657.80 (C51 H31 N = 657.80) 55 m / z = 614.76 (C44H26N2 = 614.18) 56 m / z = 614.76 (C44H26N2S = 614.18) 57 m / z = 625.72 (C45H27N3O = 625.22) 58 m / z = 571.66 (C43H25NO = 571.19) 59 m / z = 587.73 (C43H25NS = 587.17) 60 m / z = 646.78 (C49H30N2 = 646.24) 61 m / z = 631.76 (C49H29N = 631.23) 62 m / z = 605.72 (C 47 H 27 N = 605.21) 63 m / z = 663.88 (C49H33NSi = 663.24) 64 m / z = 737.96 (C 55 H 35 NSi = 737.25) 65 m / z = 597.75 (C46 H31 N = 597.25) 66 m / z = 686.84 (C52H34N2 = 686.27) 67 m / z = 676.83 (C49H28N2S = 676.20) 68 m / z = 660.76 (C49H28N2O = 660.22) 69 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 70 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 71 m / z = 570.68 (C43H26N2 = 570.21) 72 m / z = 724.89 (C 55 H 36 N 2 = 724.29) 73 m / z = 764.95 (C 58 H 40 N 2 = 764.32) 74 m / z = 646.78 (C49H30N2 = 646.24) 75 m / z = 800.98 (C61 H40 N2 = 800.32) 76 m / z = 636.74 (C46H28N4 = 636.23) 77 m / z = 673.80 (C50 H31 N3 = 673.25) 78 m / z = 673.80 (C50 H31 N3 = 673.25) 79 m / z = 605.66 (C43H28NOP = 605.19) 90 m / z = 532.63 (C40H24N2 = 532.19) 81 m / z = 532.63 (C40H24N2 = 532.19) 82 m / z = 635.75 (C 47 H 29 N 3 = 635.75) 83 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 84 m / z = 811.97 (C61 H37 N3 = 811.30) 85 m / z = 682.81 (C52H30N2 = 682.24) 86 m / z = 581.70 (C45 H27 N = 581.21) 87 m / z = 685.81 (C51 H31 N3 = 685.25) 88 m / z = 711.85 (C53H33N3 = 711.27) 89 m / z = 657.80 (51C31HN = 657.25) 90 m / z = 614.76 (C44H26N2S = 614.18) 91 m / z = 614.76 (C44H26N2 = 614.18) 92 m / z = 625.72 (C45H27N3O = 625.72) 93 m / z = 571.66 (C43H25NO = 571.19) 94 m / z = 587.73 (C43H25NS = 587.17) 95 m / z = 646.78 (C49H30N2 = 646.24) 96 m / z = 631.76 (C49H29N = 631.23) 97 m / z = 605.72 (C 47 H 27 N = 605.21) 98 m / z = 663.88 (C49H33NSi = 663.24) 99 m / z = 737.96 (C 55 H 35 NSi = 737.25) 100 m / z = 597.75 (C46 H31 N = 597.25) 101 m / z = 455.55 (C35H21N = 455.17) 102 m / z = 405.49 (C31 H19 N = 405.15) 103 m / z = 455.55 (C35H21N = 455.17) 104 m / z = 721.88 (C56 H35 N = 721.28) 105 m / z = 711.85 (C53H33N3 = 711.27) 106 m / z = 686.84 (C52H34N2 = 686.27) 107 m / z = 676.83 (C49H28N2S = 676.20) 108 m / z = 660.76 (C49H28N2O = 660.22) 109 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 110 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 111 m / z = 570.68 (C43H26N2 = 570.21) 112 m / z = 724.89 (C 55 H 36 N 2 = 724.29) 113 m / z = 764.95 (C 58 H 40 N 2 = 764.32) 114 m / z = 646.789 (C49H30N2 = 646.24) 115 m / z = 800.98 (C61 H40 N2 = 800.32) 116 m / z = 636.74 (C46H28N4 = 636.23) 117 m / z = 673.80 (C50 H31 N3 = 673.25) 118 m / z = 673.80 (C40H31N3 = 673.25) 119 m / z = 605.66 (C43H28NOP = 605.19) 120 m / z = 532.63 (C40H24N2 = 532.19) 121 m / z = 532.63 (C40H24N2 = 532.19) 122 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 123 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 124 m / z = 811.97 (C61 H37 N3 = 811.30) 125 m / z = 682.81 (C52H30N2 = 682.24) 126 m / z = 581.70 (C45 H27 N = 581.21) 127 m / z = 685.81 (C51 H31 N3 = 685.25) 128 m / z = 711.85 (C53H33N3 = 711.27) 129 m / z = 657.80 (C51 H31 N = 657.80) 130 m / z = 614.76 (C44H26N2 = 614.18) 131 m / z = 614.76 (C44H26N2S = 614.18) 132 m / z = 625.72 (C45H27N3O = 625.22) 133 m / z = 571.66 (C43H25NO = 571.19) 134 m / z = 587.73 (C43H25NS = 587.17) 135 m / z = 646.78 (C49H30N2 = 646.24) 136 m / z = 631.76 (C49H29N = 631.23) 137 m / z = 605.72 (C 47 H 27 N = 605.21) 138 m / z = 663.88 (C49H33NSi = 663.24) 139 m / z = 737.96 (C 55 H 35 NSi = 737.25) 140 m / z = 597.75 (C46 H31 N = 597.25) 141 m / z = 686.84 (C52H34N2 = 686.27) 142 m / z = 676.83 (C49H28N2S = 676.20) 143 m / z = 660.76 (C49H28N2O = 660.22) 144 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 145 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 146 m / z = 570.68 (C43H26N2 = 570.21) 147 m / z = 724.89 (C 55 H 36 N 2 = 724.29) 148 m / z = 764.95 (C 58 H 40 N 2 = 764.32) 149 m / z = 646.78 (C49H30N2 = 646.24) 150 m / z = 800.98 (C61 H40 N2 = 800.32) 151 m / z = 636.74 (C46H28N4 = 63623) 152 m / z = 673.80 (C50 H31 N3 = 673.25) 153 m / z = 673.80 (C50 H31 N3 = 673.25) 154 m / z = 605.66 (C43H28NOP = 605.19) 155 m / z = 532.63 (C40H24N2 = 532.19) 156 m / z = 532.63 (C40H24N2 = 532.19) 157 m / z = 635.75 (C 47 H 29 N 3 = 635.75) 158 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 159 m / z = 811.97 (C61 H37 N3 = 811.30) 160 m / z = 682.81 (C52H30N2 = 682.24) 161 m / z = 581.70 (C45 H27 N = 581.21) 162 m / z = 685.81 (C51 H31 N3 = 685.25) 163 m / z = 711.85 (C53H33N3 = 711.27) 164 m / z = 657.80 (51C31HN = 657.25) 165 m / z = 614.76 (C44H26N2S = 614.18) 166 m / z = 614.76 (C44H26N2 = 614.18) 167 m / z = 625.72 (C45H27N3O = 625.72) 168 m / z = 571.66 (C43H25NO = 571.19) 169 m / z = 587.73 (C43H25NS = 587.17) 170 m / z = 646.78 (C49H30N2 = 646.24) 171 m / z = 631.76 (C49H29N = 631.23) 172 m / z = 605.72 (C 47 H 27 N = 605.21) 173 m / z = 663.88 (C49H33NSi = 663.24) 174 m / z = 737.96 (C 55 H 35 NSi = 737.25) 175 m / z = 597.75 (C46 H31 N = 597.25) 176 m / z = 455.55 (C35H21N = 455.17) 177 m / z = 405.49 (C31 H19 N = 405.15) 178 m / z = 455.55 (C35H21N = 455.17) 179 m / z = 721.88 (C56 H35 N = 721.28) 180 m / z = 711.85 (C53H33N3 = 711.27) 181 m / z = 686.84 (C52H34N2 = 686.27) 182 m / z = 676.83 (C49H28N2S = 676.20) 183 m / z = 660.76 (C49H28N2O = 660.22) 184 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 185 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 186 m / z = 570.68 (C43H26N2 = 570.21) 187 m / z = 724.89 (C 55 H 36 N 2 = 724.29) 188 m / z = 764.95 (C 58 H 40 N 2 = 764.32) 189 m / z = 646.789 (C49H30N2 = 646.24) 190 m / z = 800.98 (C61 H40 N2 = 800.32) 191 m / z = 636.74 (C46H28N4 = 636.23) 192 m / z = 673.80 (C50 H31 N3 = 673.25) 193 m / z = 673.80 (C40H31N3 = 673.25) 194 m / z = 605.66 (C43H28NOP = 605.19) 195 m / z = 532.63 (C40H24N2 = 532.19) 196 m / z = 532.63 (C40H24N2 = 532.19) 197 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 198 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 199 m / z = 811.97 (C61 H37 N3 = 811.30) 200 m / z = 682.81 (C52H30N2 = 682.24) 201 m / z = 581.70 (C45 H27 N = 581.21) 202 m / z = 685.81 (C51 H31 N3 = 685.25) 203 m / z = 711.85 (C53H33N3 = 711.27) 204 m / z = 657.80 (C51 H31 N = 657.80) 205 m / z = 614.76 (C44H26N2 = 614.18) 206 m / z = 614.76 (C44H26N2S = 614.18) 207 m / z = 625.72 (C45H27N3O = 625.22) 208 m / z = 571.66 (C43H25NO = 571.19) 209 m / z = 587.73 (C43H25NS = 587.17) 210 m / z = 646.78 (C49H30N2 = 646.24) 211 m / z = 631.76 (C49H29N = 631.23) 212 m / z = 605.72 (C 47 H 27 N = 605.21) 213 m / z = 663.88 (C49H33NSi = 663.24) 214 m / z = 737.96 (C 55 H 35 NSi = 737.25) 215 m / z = 597.75 (C46 H31 N = 597.25) 216 m / z = 686.84 (C52H34N2 = 686.27) 217 m / z = 676.83 (C49H28N2S = 676.20) 218 m / z = 660.76 (C49H28N2O = 660.22) 219 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 220 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 221 m / z = 570.68 (C43H26N2 = 570.21) 222 m / z = 724.89 (C 55 H 36 N 2 = 724.29) 223 m / z = 764.95 (C 58 H 40 N 2 = 764.32) 224 m / z = 646.78 (C49H30N2 = 646.24) 225 m / z = 800.98 (C61 H40 N2 = 800.32) 226 m / z = 834.01 (C65H39N = 833.31) 227 m / z = 834.01 (C65H39N = 833.31) 228 m / z = 707.86 (C 55 H 33 N = 707.26) 229 m / z = 707.86 (C 55 H 33 N = 707.26) 230 m / z = 657.80 (C51 H31 N = 657.25) 231 m / z = 834.01 (C65H39N = 833.31) 232 m / z = 834.01 (C65H39N = 833.31) 233 m / z = 707.86 (C 55 H 33 N = 707.26) 234 m / z = 707.86 (C 55 H 33 N = 707.26) 235 m / z = 657.80 (C51 H31 N = 657.25) 236 m / z = 681.76 (C49H32NOP = 681.22) 237 m / z = 681.76 (C49H32NOP = 681.22) 238 m / z = 681.76 (C49H32NOP = 681.22) 239 m / z = 681.76 (C49H32NOP = 681.22) 240 m / z = 638.72 (C44H26N6 = 638.22) 241 m / z = 638.72 (C44H26N6 = 638.72) 242 m / z = 638.72 (C44H26N6 = 638.22) 243 m / z = 737.86 (C54 H32 N4 = 736.26) 244 m / z = 737.86 (C54 H32 N4 = 736.26) 245 m / z = 836.98 (C62H36N4 = 836.29) 246 m / z = 712.86 (C52H32N4 = 712.26) 247 m / z = 714.81 (C50H30N6 = 714.25) 248 m / z = 714.81 (C50H30N6 = 714.25) 249 m / z = 714.81 (C50H30N6 = 714.25) 250 m / z = 812.95 (C60H36N4 = 812.29) 251 m / z = 812.95 (C60H36N4 = 812.29) 252 m / z = 913.33 (C68H40N4 = 913.07) 253 m / z = 712.84 (C52H32N4 = 712.26) 254 m / z = 714.81 (C50H30N6 = 714.25) 255 m / z = 714.81 (C50H30N6 = 714.25) 256 m / z = 714.81 (C50H30N6 = 714.25) 257 m / z = 812.95 (C60H36N4 = 812.29) 258 m / z = 812.95 (C60H36N4 = 812.29) 259 m / z = 913.07 (C68H40N4 = 912.33) 260 m / z = 638.72 (C44H26N6 = 638.22) 261 m / z = 638.72 (C44H26N6 = 638.72) 262 m / z = 638.72 (C44H26N6 = 638.22) 263 m / z = 737.86 (C54 H32 N4 = 736.26) 264 m / z = 737.86 (C54 H32 N4 = 736.26) 265 m / z = 836.98 (C62H36N4 = 836.29) 266 m / z = 712.86 (C52H32N4 = 712.26) 267 m / z = 714.81 (C50H30N6 = 714.25) 268 m / z = 714.81 (C50H30N6 = 714.25) 269 m / z = 714.81 (C50H30N6 = 714.25) 270 m / z = 812.95 (C60H36N4 = 812.29) 271 m / z = 812.95 (C60H36N4 = 812.29) 272 m / z = 913.33 (C68H40N4 = 913.07) 273 m / z = 712.84 (C52H32N4 = 712.26) 274 m / z = 714.81 (C50H30N6 = 714.25) 275 m / z = 714.81 (C50H30N6 = 714.25) 276 m / z = 714.81 (C50H30N6 = 714.25) 277 m / z = 812.95 (C60H36N4 = 812.29) 278 m / z = 812.95 (C60H36N4 = 812.29) 279 m / z = 913.07 (C68H40N4 = 912.33) 280 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 281 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 282 m / z = 835.99 (C 63 H 37 N 3 = 835.30) 283 m / z = 787.95 (C59 H37 N3 = 787.30) 284 m / z = 711.85 (C53H33N3 = 711.27) 285 m / z = 787.95 (C59 H37 N3 = 787.30) 286 m / z = 711.85 (C53H33N3 = 711.27) 287 m / z = 711.85 (C53H33N3 = 711.27) 288 m / z = 811.97 (C61 H37 N3 = 811.30) 289 m / z = 811.97 (C61 H37 N3 = 811.30) 290 m / z = 912.08 (C69H41N3 = 911.33) 291 m / z = 864.04 (C65H41N3 = 863.33) 292 m / z = 787.95 (C59 H37 N3 = 787.30) 293 m / z = 864.04 (C65H41N3 = 863.33) 294 m / z = 787.95 (C59 H37 N3 = 787.30) 295 m / z = 711.85 (C53H33N3 = 711.27) 296 m / z = 811.97 (C61 H37 N3 = 811.30) 297 m / z = 811.97 (C61 H37 N3 = 811.30) 298 m / z = 912.08 (C69H41N3 = 911.33) 299 m / z = 864.04 (C65H41N3 = 863.33) 300 m / z = 787.95 (C59 H37 N3 = 787.30) 301 m / z = 864.04 (C65H41N3 = 863.33) 302 m / z = 787.95 (C59 H37 N3 = 787.30) 303 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 304 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 305 m / z = 835.99 (C 63 H 37 N 3 = 835.30) 306 m / z = 787.95 (C59 H37 N3 = 787.30) 307 m / z = 711.85 (C53H33N3 = 711.27) 308 m / z = 787.95 (C59 H37 N3 = 787.30) 309 m / z = 711.85 (C53H33N3 = 711.27) 310 m / z = 711.85 (C53H33N3 = 711.27) 311 m / z = 811.97 (C61 H37 N3 = 811.30) 312 m / z = 811.97 (C61 H37 N3 = 811.30) 313 m / z = 912.08 (C69H41N3 = 911.33) 314 m / z = 864.04 (C65H41N3 = 863.33) 315 m / z = 787.95 (C59 H37 N3 = 787.30) 316 m / z = 864.04 (C65H41N3 = 863.33) 317 m / z = 787.95 (C59 H37 N3 = 787.30) 318 m / z = 711.85 (C53H33N3 = 711.27) 319 m / z = 811.97 (C61 H37 N3 = 811.30) 320 m / z = 811.97 (C61 H37 N3 = 811.30) 321 m / z = 912.08 (C69H41N3 = 911.33) 322 m / z = 864.04 (C65H41N3 = 863.33) 323 m / z = 787.95 (C59 H37 N3 = 787.30) 324 m / z = 864.04 (C65H41N3 = 863.33) 325 m / z = 787.95 (C59 H37 N3 = 787.30) 326 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 327 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 328 m / z = 835.99 (C 63 H 37 N 3 = 835.30) 329 m / z = 787.95 (C59 H37 N3 = 787.30) 330 m / z = 711.85 (C53H33N3 = 711.27) 331 m / z = 787.95 (C59 H37 N3 = 787.30) 332 m / z = 711.85 (C53H33N3 = 711.27) 333 m / z = 711.85 (C53H33N3 = 711.27) 334 m / z = 636.74 (C46H28N4 = 636.23) 335 m / z = 712.84 (C52H32N4 = 712.26) 336 m / z = 712.84 (C52H32N4 = 712.26) 337 m / z = 711.85 (C53H33N3 = 711.27) 338 m / z = 811.97 (C61 H37 N3 = 811.30) 339 m / z = 811.97 (C61 H37 N3 = 811.30) 340 m / z = 912.08 (C69H41N3 = 911.33) 341 m / z = 864.04 (C65H41N3 = 863.33) 342 m / z = 787.95 (C59 H37 N3 = 787.30) 343 m / z = 787.95 (C59 H37 N3 = 787.30) 344 m / z = 864.04 (C65H41N3 = 863.33) 345 m / z = 787.95 (C59 H37 N3 = 787.30) 346 m / z = 787.95 (C59 H37 N3 = 787.30) 347 m / z = 712.84 (C52H32N4 = 712.26) 348 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 349 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 350 m / z = 811.97 (C61 H37 N3 = 811.30) 351 m / z = 811.97 (C61 H37 N3 = 811.30) 352 m / z = 912.08 (C69H41N3 = 911.33) 353 m / z = 864.04 (C65H41N3 = 863.33) 354 m / z = 787.95 (C59 H37 N3 = 787.30) 355 m / z = 787.95 (C59 H37 N3 = 787.30) 356 m / z = 864.04 (C65H41N3 = 863.33) 357 m / z = 787.95 (C59 H37 N3 = 787.30) 358 m / z = 787.95 (C59 H37 N3 = 787.30) 359 m / z = 712.84 (C52H32N4 = 712.26) 360 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 361 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 362 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 363 m / z = 835.99 (C 63 H 37 N 3 = 835.30) 364 m / z = 787.95 (C59 H37 N3 = 787.30) 365 m / z = 711.85 (C53H33N3 = 711.27) 366 m / z = 787.95 (C59 H37 N3 = 787.30) 367 m / z = 711.85 (C53H33N3 = 711.27) 368 m / z = 711.85 (C53H33N3 = 711.27) 369 m / z = 636.74 (C46H28N4 = 636.23) 370 m / z = 712.84 (C52H32N4 = 712.26) 371 m / z = 712.84 (C52H32N4 = 712.26) 372 m / z = 711.85 (C53H33N3 = 711.27) 373 m / z = 811.97 (C61 H37 N3 = 811.30) 374 m / z = 811.97 (C61 H37 N3 = 811.30) 375 m / z = 912.08 (C69H41N3 = 911.33) 376 m / z = 864.04 (C65H41N3 = 863.33) 377 m / z = 787.95 (C59 H37 N3 = 787.30) 378 m / z = 787.95 (C59 H37 N3 = 787.30) 379 m / z = 864.04 (C65H41N3 = 863.33) 380 m / z = 787.95 (C59 H37 N3 = 787.30) 381 m / z = 787.95 (C59 H37 N3 = 787.30) 382 m / z = 712.84 (C52H32N4 = 712.26) 383 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 384 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 385 m / z = 811.97 (C61 H37 N3 = 811.30) 386 m / z = 811.97 (C61 H37 N3 = 811.30) 387 m / z = 912.08 (C69H41N3 = 911.33) 388 m / z = 864.04 (C65H41N3 = 863.33) 389 m / z = 787.95 (C59 H37 N3 = 787.30) 390 m / z = 787.95 (C59 H37 N3 = 787.30) 391 m / z = 864.04 (C65H41N3 = 863.33) 392 m / z = 787.95 (C59 H37 N3 = 787.30) 393 m / z = 787.95 (C59 H37 N3 = 787.30) 394 m / z = 712.84 (C52H32N4 = 712.26) 395 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 396 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 397 m / z = 609.72 (C45H27N3 = 609.22) 398 m / z = 685.81 (C51 H31 N3 = 685.25) 399 m / z = 659.77 (C49 H29 N3 = 659.24) 400 m / z = 659.77 (C49 H29 N3 = 659.24) 401 m / z = 685.81 (C51 H31 N3 = 685.25) 402 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 403 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 404 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 405 m / z = 685.81 (C51 H31 N3 = 685.25) 406 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 407 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 408 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 409 m / z = 609.72 (C45H27N3 = 609.22) 410 m / z = 685.81 (C51 H31 N3 = 685.25) 411 m / z = 659.77 (C49 H29 N3 = 659.24) 412 m / z = 659.77 (C49 H29 N3 = 659.24) 413 m / z = 685.81 (C51 H31 N3 = 685.25) 414 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 415 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 416 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 417 m / z = 685.81 (C51 H31 N3 = 685.25) 418 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 419 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 420 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 421 m / z = 864.04 (C65H41N3 = 863.33) 422 m / z = 864.04 (C65H41N3 = 863.33) 423 m / z = 811.97 (C61 H37 N3 = 811.30) 424 m / z = 811.97 (C61 H37 N3 = 811.30) 425 m / z = 787.95 (C59 H37 N3 = 787.30) 426 m / z = 787.95 (C59 H37 N3 = 787.30) 427 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 428 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 429 m / z = 811.97 (C61 H37 N3 = 811.30) 430 m / z = 864.04 (C65H41N3 = 863.33) 431 m / z = 864.04 (C65H41N3 = 863.33) 432 m / z = 811.97 (C61 H37 N3 = 811.30) 433 m / z = 811.97 (C61 H37 N3 = 811.30) 434 m / z = 787.95 (C59 H37 N3 = 787.30) 435 m / z = 787.95 (C59 H37 N3 = 787.30) 436 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 437 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 438 m / z = 811.97 (C61 H37 N3 = 811.30) 439 m / z = 609.72 (C45H27N3 = 609.22) 440 m / z = 685.81 (C51 H31 N3 = 685.25) 441 m / z = 685.81 (C51 H31 N3 = 685.25) 442 m / z = 685.81 (C51 H31 N3 = 685.25) 443 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 444 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 445 m / z = 685.81 (C51 H31 N3 = 685.25) 446 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 447 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 448 m / z = 609.72 (C45H27N3 = 609.22) 449 m / z = 685.81 (C51 H31 N3 = 685.25) 450 m / z = 685.81 (C51 H31 N3 = 685.25) 451 m / z = 685.81 (C51 H31 N3 = 685.25) 452 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 453 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 454 m / z = 685.81 (C51 H31 N3 = 685.25) 455 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 456 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 457 m / z = 583.20 (C43 H25 N3 = 583.20) 458 m / z = 659.77 (C49 H29 N3 = 659.24) 459 m / z = 659.77 (C49 H29 N3 = 659.24) 460 m / z = 583.20 (C43 H25 N3 = 583.20) 461 m / z = 659.77 (C49 H29 N3 = 659.24) 462 m / z = 659.77 (C49 H29 N3 = 659.24) 463 m / z = 597.71 (C44H27N3 = 592.22) 464 m / z = 597.71 (C44H27N3 = 592.22) 465 m / z = 597.71 (C44H27N3 = 592.22) 466 m / z = 597.71 (C44H27N3 = 592.22) 467 m / z = 597.71 (C44H27N3 = 592.22) 468 m / z = 597.71 (C44H27N3 = 592.22) 469 m / z = 597.71 (C44H27N3 = 592.22) 470 m / z = 597.71 (C44H27N3 = 592.22) 471 m / z = 549.66 (C40H27N3 = 549.22) 472 m / z = 625.76 (C46 H31 N3 = 625.25) 473 m / z = 625.76 (C46 H31 N3 = 625.25) 474 m / z = 625.76 (C46 H31 N3 = 625.25) 475 m / z = 625.76 (C46 H31 N3 = 625.25) 476 m / z = 549.66 (C40H27N3 = 549.22) 477 m / z = 549.66 (C40H27N3 = 549.22) 478 m / z = 625.76 (C46 H31 N3 = 625.25) 479 m / z = 625.76 (C46 H31 N3 = 625.25) 480 m / z = 625.76 (C46 H31 N3 = 625.25) 481 m / z = 625.76 (C46 H31 N3 = 625.25) 482 m / z = 549.66 (C40H27N3 = 549.22) 483 m / z = 614.76 (C44H26N2S = 614.18) 484 m / z = 614.76 (C44H26N2S = 614.18) 485 m / z = 614.76 (C44H26N2S = 614.18) 486 m / z = 614.76 (C44H26N2S = 614.18) 487 m / z = 634.77 (C48H30N2 = 634.24) 488 m / z = 710.86 (C54 H34 N2 = 710.27) 489 m / z = 636.74 (C46H28N4 = 636.23) 490 m / z = 636.74 (C46H28N4 = 636.23) 491 m / z = 636.74 (C46H28N4 = 636.23) 492 m / z = 712.84 (C52H32N4 = 712.26) 493 m / z = 712.84 (C52H32N4 = 712.26) 494 m / z = 712.84 (C52H32N4 = 712.26) 495 m / z = 559.66 (C41 H25 N3 = 559.20) 496 m / z = 559.66 (C41 H25 N3 = 559.20) 497 m / z = 559.66 (C41 H25 N3 = 559.20) 498 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 499 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 500 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 501 m / z = 634.77 (C48H30N2 = 634.24) 502 m / z = 710.86 (C54 H34 N2 = 710.27) 503 m / z = 636.74 (C46H28N4 = 636.23) 504 m / z = 636.74 (C46H28N4 = 636.23) 505 m / z = 636.74 (C46H28N4 = 636.23) 506 m / z = 712.84 (C52H32N4 = 712.26) 507 m / z = 712.84 (C52H32N4 = 712.26) 508 m / z = 712.84 (C52H32N4 = 712.26) 509 m / z = 559.66 (C41 H25 N3 = 559.20) 510 m / z = 559.66 (C41 H25 N3 = 559.20) 511 m / z = 559.66 (C41 H25 N3 = 559.20) 512 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 513 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 514 m / z = 834.01 (C65H39N = 833.31) 515 m / z = 834.01 (C65H39N = 833.31) 516 m / z = 707.86 (C 55 H 33 N = 707.26) 517 m / z = 707.86 (C 55 H 33 N = 707.26) 518 m / z = 657.80 (C51 H31 N = 657.25) 519 m / z = 834.01 (C65H39N = 833.31) 520 m / z = 834.01 (C65H39N = 833.31) 521 m / z = 707.86 (C 55 H 33 N = 707.26) 522 m / z = 707.86 (C 55 H 33 N = 707.26) 523 m / z = 657.80 (C51 H31 N = 657.25) 524 m / z = 681.76 (C49H32NOP = 681.22) 525 m / z = 681.76 (C49H32NOP = 681.22) 526 m / z = 681.76 (C49H32NOP = 681.22) 527 m / z = 681.76 (C49H32NOP = 681.22) 528 m / z = 638.72 (C44H26N6 = 638.22) 529 m / z = 638.72 (C44H26N6 = 638.72) 530 m / z = 638.72 (C44H26N6 = 638.22) 531 m / z = 737.86 (C54 H32 N4 = 736.26) 532 m / z = 737.86 (C54 H32 N4 = 736.26) 533 m / z = 836.98 (C62H36N4 = 836.29) 534 m / z = 712.86 (C52H32N4 = 712.26) 535 m / z = 714.81 (C50H30N6 = 714.25) 536 m / z = 714.81 (C50H30N6 = 714.25) 537 m / z = 714.81 (C50H30N6 = 714.25) 538 m / z = 812.95 (C60H36N4 = 812.29) 539 m / z = 812.95 (C60H36N4 = 812.29) 540 m / z = 913.33 (C68H40N4 = 913.07) 541 m / z = 712.84 (C52H32N4 = 712.26) 542 m / z = 714.81 (C50H30N6 = 714.25) 543 m / z = 714.81 (C50H30N6 = 714.25) 544 m / z = 714.81 (C50H30N6 = 714.25) 545 m / z = 812.95 (C60H36N4 = 812.29) 546 m / z = 812.95 (C60H36N4 = 812.29) 547 m / z = 913.07 (C68H40N4 = 912.33) 548 m / z = 638.72 (C44H26N6 = 638.22) 549 m / z = 638.72 (C44H26N6 = 638.72) 550 m / z = 638.72 (C44H26N6 = 638.22) 551 m / z = 737.86 (C54 H32 N4 = 736.26) 552 m / z = 737.86 (C54 H32 N4 = 736.26) 553 m / z = 836.98 (C62H36N4 = 836.29) 554 m / z = 712.86 (C52H32N4 = 712.26) 555 m / z = 714.81 (C50H30N6 = 714.25) 556 m / z = 714.81 (C50H30N6 = 714.25) 557 m / z = 714.81 (C50H30N6 = 714.25) 558 m / z = 812.95 (C60H36N4 = 812.29) 559 m / z = 812.95 (C60H36N4 = 812.29) 560 m / z = 913.33 (C68H40N4 = 913.07) 561 m / z = 712.84 (C52H32N4 = 712.26) 562 m / z = 714.81 (C50H30N6 = 714.25) 563 m / z = 714.81 (C50H30N6 = 714.25) 564 m / z = 714.81 (C50H30N6 = 714.25) 565 m / z = 812.95 (C60H36N4 = 812.29) 566 m / z = 812.95 (C60H36N4 = 812.29) 567 m / z = 913.07 (C68H40N4 = 912.33) 568 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 569 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 570 m / z = 835.99 (C 63 H 37 N 3 = 835.30) 571 m / z = 787.95 (C59 H37 N3 = 787.30) 572 m / z = 711.85 (C53H33N3 = 711.27) 573 m / z = 787.95 (C59 H37 N3 = 787.30) 574 m / z = 711.85 (C53H33N3 = 711.27) 575 m / z = 711.85 (C53H33N3 = 711.27) 576 m / z = 811.97 (C61 H37 N3 = 811.30) 577 m / z = 811.97 (C61 H37 N3 = 811.30) 578 m / z = 912.08 (C69H41N3 = 911.33) 579 m / z = 864.04 (C65H41N3 = 863.33) 580 m / z = 787.95 (C59 H37 N3 = 787.30) 581 m / z = 864.04 (C65H41N3 = 863.33) 582 m / z = 787.95 (C59 H37 N3 = 787.30) 583 m / z = 711.85 (C53H33N3 = 711.27) 584 m / z = 811.97 (C61 H37 N3 = 811.30) 585 m / z = 811.97 (C61 H37 N3 = 811.30) 586 m / z = 912.08 (C69H41N3 = 911.33) 587 m / z = 864.04 (C65H41N3 = 863.33) 588 m / z = 787.95 (C59 H37 N3 = 787.30) 589 m / z = 864.04 (C65H41N3 = 863.33) 590 m / z = 787.95 (C59 H37 N3 = 787.30) 591 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 592 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 593 m / z = 835.99 (C 63 H 37 N 3 = 835.30) 594 m / z = 787.95 (C59 H37 N3 = 787.30) 595 m / z = 711.85 (C53H33N3 = 711.27) 596 m / z = 787.95 (C59 H37 N3 = 787.30) 597 m / z = 711.85 (C53H33N3 = 711.27) 598 m / z = 711.85 (C53H33N3 = 711.27) 599 m / z = 811.97 (C61 H37 N3 = 811.30) 600 m / z = 811.97 (C61 H37 N3 = 811.30) 601 m / z = 912.08 (C69H41N3 = 911.33) 602 m / z = 864.04 (C65H41N3 = 863.33) 603 m / z = 787.95 (C59 H37 N3 = 787.30) 604 m / z = 864.04 (C65H41N3 = 863.33) 605 m / z = 787.95 (C59 H37 N3 = 787.30) 606 m / z = 711.85 (C53H33N3 = 711.27) 607 m / z = 811.97 (C61 H37 N3 = 811.30) 608 m / z = 811.97 (C61 H37 N3 = 811.30) 609 m / z = 912.08 (C69H41N3 = 911.33) 610 m / z = 864.04 (C65H41N3 = 863.33) 611 m / z = 787.95 (C59 H37 N3 = 787.30) 612 m / z = 864.04 (C65H41N3 = 863.33) 613 m / z = 787.95 (C59 H37 N3 = 787.30) 614 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 615 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 616 m / z = 835.99 (C 63 H 37 N 3 = 835.30) 617 m / z = 787.95 (C59 H37 N3 = 787.30) 618 m / z = 711.85 (C53H33N3 = 711.27) 619 m / z = 787.95 (C59 H37 N3 = 787.30) 620 m / z = 711.85 (C53H33N3 = 711.27) 621 m / z = 711.85 (C53H33N3 = 711.27) 622 m / z = 636.74 (C46H28N4 = 636.23) 623 m / z = 712.84 (C52H32N4 = 712.26) 624 m / z = 712.84 (C52H32N4 = 712.26) 625 m / z = 711.85 (C53H33N3 = 711.27) 626 m / z = 811.97 (C61 H37 N3 = 811.30) 627 m / z = 811.97 (C61 H37 N3 = 811.30) 628 m / z = 912.08 (C69H41N3 = 911.33) 629 m / z = 864.04 (C65H41N3 = 863.33) 630 m / z = 787.95 (C59 H37 N3 = 787.30) 631 m / z = 787.95 (C59 H37 N3 = 787.30) 632 m / z = 864.04 (C65H41N3 = 863.33) 633 m / z = 787.95 (C59 H37 N3 = 787.30) 634 m / z = 787.95 (C59 H37 N3 = 787.30) 635 m / z = 712.84 (C52H32N4 = 712.26) 636 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 637 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 638 m / z = 811.97 (C61 H37 N3 = 811.30) 639 m / z = 811.97 (C61 H37 N3 = 811.30) 640 m / z = 912.08 (C69H41N3 = 911.33) 641 m / z = 864.04 (C65H41N3 = 863.33) 642 m / z = 787.95 (C59 H37 N3 = 787.30) 643 m / z = 787.95 (C59 H37 N3 = 787.30) 644 m / z = 864.04 (C65H41N3 = 863.33) 645 m / z = 787.95 (C59 H37 N3 = 787.30) 646 m / z = 787.95 (C59 H37 N3 = 787.30) 647 m / z = 712.84 (C52H32N4 = 712.26) 648 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 649 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 650 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 651 m / z = 835.99 (C 63 H 37 N 3 = 835.30) 652 m / z = 787.95 (C59 H37 N3 = 787.30) 653 m / z = 711.85 (C53H33N3 = 711.27) 654 m / z = 787.95 (C59 H37 N3 = 787.30) 655 m / z = 711.85 (C53H33N3 = 711.27) 656 m / z = 711.85 (C53H33N3 = 711.27) 657 m / z = 636.74 (C46H28N4 = 636.23) 658 m / z = 712.84 (C52H32N4 = 712.26) 659 m / z = 712.84 (C52H32N4 = 712.26) 660 m / z = 711.85 (C53H33N3 = 711.27) 661 m / z = 811.97 (C61 H37 N3 = 811.30) 662 m / z = 811.97 (C61 H37 N3 = 811.30) 663 m / z = 912.08 (C69H41N3 = 911.33) 664 m / z = 864.04 (C65H41N3 = 863.33) 665 m / z = 787.95 (C59 H37 N3 = 787.30) 666 m / z = 787.95 (C59 H37 N3 = 787.30) 667 m / z = 864.04 (C65H41N3 = 863.33) 668 m / z = 787.95 (C59 H37 N3 = 787.30) 669 m / z = 787.95 (C59 H37 N3 = 787.30) 670 m / z = 712.84 (C52H32N4 = 712.26) 671 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 672 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 673 m / z = 811.97 (C61 H37 N3 = 811.30) 674 m / z = 811.97 (C61 H37 N3 = 811.30) 675 m / z = 912.08 (C69H41N3 = 911.33) 676 m / z = 864.04 (C65H41N3 = 863.33) 677 m / z = 787.95 (C59 H37 N3 = 787.30) 678 m / z = 787.95 (C59 H37 N3 = 787.30) 679 m / z = 864.04 (C65H41N3 = 863.33) 680 m / z = 787.95 (C59 H37 N3 = 787.30) 681 m / z = 787.95 (C59 H37 N3 = 787.30) 682 m / z = 712.84 (C52H32N4 = 712.26) 683 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 684 m / z = 788.93 (C 58 H 36 N 4 = 788.29) 685 m / z = 609.72 (C45H27N3 = 609.22) 686 m / z = 685.81 (C51 H31 N3 = 685.25) 687 m / z = 659.77 (C49 H29 N3 = 659.24) 688 m / z = 659.77 (C49 H29 N3 = 659.24) 689 m / z = 685.81 (C51 H31 N3 = 685.25) 690 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 691 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 692 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 693 m / z = 685.81 (C51 H31 N3 = 685.25) 694 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 695 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 696 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 697 m / z = 609.72 (C45H27N3 = 609.22) 698 m / z = 685.81 (C51 H31 N3 = 685.25) 699 m / z = 659.77 (C49 H29 N3 = 659.24) 700 m / z = 659.77 (C49 H29 N3 = 659.24) 701 m / z = 685.81 (C51 H31 N3 = 685.25) 702 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 703 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 704 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 705 m / z = 685.81 (C51 H31 N3 = 685.25) 706 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 707 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 708 m / z = 735.87 (C 55 H 33 N 3 = 735.27) 709 m / z = 864.04 (C65H41N3 = 863.33) 710 m / z = 864.04 (C65H41N3 = 863.33) 711 m / z = 811.97 (C61 H37 N3 = 811.30) 712 m / z = 811.97 (C61 H37 N3 = 811.30) 713 m / z = 787.95 (C59 H37 N3 = 787.30) 714 m / z = 787.95 (C59 H37 N3 = 787.30) 715 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 716 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 717 m / z = 811.97 (C61 H37 N3 = 811.30) 718 m / z = 864.04 (C65H41N3 = 863.33) 719 m / z = 864.04 (C65H41N3 = 863.33) 720 m / z = 811.97 (C61 H37 N3 = 811.30) 721 m / z = 811.97 (C61 H37 N3 = 811.30) 722 m / z = 787.95 (C59 H37 N3 = 787.30) 723 m / z = 787.95 (C59 H37 N3 = 787.30) 724 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 725 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 726 m / z = 811.97 (C61 H37 N3 = 811.30) 727 m / z = 609.72 (C45H27N3 = 609.22) 728 m / z = 685.81 (C51 H31 N3 = 685.25) 729 m / z = 685.81 (C51 H31 N3 = 685.25) 730 m / z = 685.81 (C51 H31 N3 = 685.25) 731 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 732 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 733 m / z = 685.81 (C51 H31 N3 = 685.25) 734 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 735 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 736 m / z = 609.72 (C45H27N3 = 609.22) 737 m / z = 685.81 (C51 H31 N3 = 685.25) 738 m / z = 685.81 (C51 H31 N3 = 685.25) 739 m / z = 685.81 (C51 H31 N3 = 685.25) 740 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 741 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 742 m / z = 685.81 (C51 H31 N3 = 685.25) 743 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 744 m / z = 761.91 (C 57 H 35 N 3 = 761.28) 745 m / z = 583.20 (C43 H25 N3 = 583.20) 746 m / z = 659.77 (C49 H29 N3 = 659.24) 747 m / z = 659.77 (C49 H29 N3 = 659.24) 748 m / z = 583.20 (C43 H25 N3 = 583.20) 749 m / z = 659.77 (C49 H29 N3 = 659.24) 759 m / z = 659.77 (C49 H29 N3 = 659.24) 751 m / z = 597.71 (C44H27N3 = 592.22) 752 m / z = 597.71 (C44H27N3 = 592.22) 753 m / z = 597.71 (C44H27N3 = 592.22) 754 m / z = 597.71 (C44H27N3 = 592.22) 755 m / z = 597.71 (C44H27N3 = 592.22) 756 m / z = 597.71 (C44H27N3 = 592.22) 757 m / z = 597.71 (C44H27N3 = 592.22) 758 m / z = 597.71 (C44H27N3 = 592.22) 759 m / z = 549.66 (C40H27N3 = 549.22) 760 m / z = 625.76 (C46 H31 N3 = 625.25) 761 m / z = 625.76 (C46 H31 N3 = 625.25) 762 m / z = 625.76 (C46 H31 N3 = 625.25) 763 m / z = 625.76 (C46 H31 N3 = 625.25) 764 m / z = 549.66 (C40H27N3 = 549.22) 765 m / z = 549.66 (C40H27N3 = 549.22) 766 m / z = 625.76 (C46 H31 N3 = 625.25) 767 m / z = 625.76 (C46 H31 N3 = 625.25) 768 m / z = 625.76 (C46 H31 N3 = 625.25) 769 m / z = 625.76 (C46 H31 N3 = 625.25) 770 m / z = 549.66 (C40H27N3 = 549.22) 771 m / z = 614.76 (C44H26N2S = 614.18) 772 m / z = 614.76 (C44H26N2S = 614.18) 773 m / z = 614.76 (C44H26N2S = 614.18) 774 m / z = 614.76 (C44H26N2S = 614.18) 775 m / z = 634.77 (C48H30N2 = 634.24) 776 m / z = 710.86 (C54 H34 N2 = 710.27) 777 m / z = 636.74 (C46H28N4 = 636.23) 778 m / z = 636.74 (C46H28N4 = 636.23) 779 m / z = 636.74 (C46H28N4 = 636.23) 780 m / z = 712.84 (C52H32N4 = 712.26) 781 m / z = 712.84 (C52H32N4 = 712.26) 782 m / z = 712.84 (C52H32N4 = 712.26) 783 m / z = 559.66 (C41 H25 N3 = 559.20) 784 m / z = 559.66 (C41 H25 N3 = 559.20) 785 m / z = 559.66 (C41 H25 N3 = 559.20) 786 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 787 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 788 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 789 m / z = 634.77 (C48H30N2 = 634.24) 790 m / z = 710.86 (C54 H34 N2 = 710.27) 791 m / z = 636.74 (C46H28N4 = 636.23) 792 m / z = 636.74 (C46H28N4 = 636.23) 793 m / z = 636.74 (C46H28N4 = 636.23) 794 m / z = 712.84 (C52H32N4 = 712.26) 795 m / z = 712.84 (C52H32N4 = 712.26) 796 m / z = 712.84 (C52H32N4 = 712.26) 797 m / z = 559.66 (C41 H25 N3 = 559.20) 798 m / z = 559.66 (C41 H25 N3 = 559.20) 799 m / z = 559.66 (C41 H25 N3 = 559.20) 800 m / z = 635.75 (C 47 H 29 N 3 = 635.24) 801 m / z = 635.75 (C 47 H 29 N 3 = 635.24)

4 to 9 are graphs showing PL absorption spectra measured by PL (Photoluminescence) or LTPL (Low Temperature Photoluminescence) in a specific UV wavelength region of a compound.

The PL measurement was performed at room temperature using a model LS55 spectrometer manufactured by Perkin Elmer. LTPL was measured using a model F7000 spectrophotometer manufactured by HITACHI under the condition of -196 ° C (77K) using liquid nitrogen.

Fig. 4 shows a graph of PL measurement at a wavelength of 230 nm of Compound 44. Fig.

5 shows a graph of the LTPL measurement of Compound 44 at a wavelength of 356 nm.

6 shows a PL measurement graph of Compound 53 at a wavelength of 269 nm.

7 is a graph showing the LTPL measurement of Compound 53 at a wavelength of 398 nm.

Fig. 8 shows a graph of PL measurement at a wavelength of 265 nm of Compound 55. Fig.

9 is a graph showing the LTPL measurement of Compound 55 at a wavelength of 376 nm.

< Comparative Example  1>

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. 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)

And a hole transport layer having a thickness of 300 A was deposited on the hole injection layer.

Figure pat00073

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 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.

Figure pat00074
Figure pat00075

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

Figure pat00076

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 1000 Å to fabricate an OLED 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.

< Example  1 to 53>

An organic electroluminescent device was fabricated in the same manner as in Comparative Example 1 except that each of the compounds synthesized in Preparation Examples 1 to 53 was used in place of E1 used in the formation of the electron transport layer in Comparative Example 1.

< Experimental Example > Organic Field  Light emitting device evaluation

The driving voltage, efficiency, color coordinates and durability (lifetime) of the organic EL device fabricated in each of Comparative Example 1 and Examples 1 to 53 were measured and evaluated at an emission luminance of 700 cd / m 2 . Table 3 shows the results.

Experimental Example Electron transport layer
matter Driving voltage
(V) efficiency
(cd / A) Color coordinates
(x, y) life span
(T 50 ) Comparative Example 1 E1 4.7 4.5 (0.15, 0.18) 330 Example 1 Compound 1 4.5 4.7 (0.15, 0.18) 350 Example 2 Compound 2 4.7 4.5 (0.15, 0.18) 400 Example 3 Compound 3 4.7 5.0 (0.15, 0.17) 360 Example 4 Compound 4 4.6 4.9 (0.15, 0.18) 365 Example 5 Compound 7 4.0 5.5 (0.15, 0.17) 340 Example 6 Compound 8 4.3 4.6 (0.15, 0.19) 345 Example 7 Compound 12 4.5 4.6 (0.15, 0.18) 338 Example 8 Compound 13 4.3 4.9 (0.15, 0.18) 366 Example 9 Compound 30 4.7 5.0 (0.15, 0.19) 334 Example 10 Compound 442 4.2 4.8 (0.15, 0.17) 340 Example 11 Compound 31 4.7 4.6 (0.15, 0.18) 333 Example 12 Compound 44 4.7 4.6 (0.15, 0.17) 450 Example 13 Compound 53 4.3 4.8 (0.15, 0.17) 370 Example 14 Compound 41 4.2 4.7 (0.15, 0.18) 355 Example 15 Compound 42 4.6 4.9 (0.15, 0.18) 370 Example 16 Compound 43 4.6 4.8 (0.15, 0.18) 390 Example 17 Compound 47 4.7 4.6 (0.15, 0.17) 380 Example 18 Compound 48 4.7 4.8 (0.15, 0.17) 385 Example 19 Compound 52 4.5 4.8 (0.15, 0.18) 355 Example 20 Compound 451 4.2 4.6 (0.15, 0.17) 357 Example 21 Compound 55 4.7 4.6 (0.15, 0.17) 337 Example 22 Compound 72 4.7 4.7 (0.15, 0.18) 343 Example 23 Compound 87 4.3 4.9 (0.15, 0.18) 365 Example 24 Compound 76 4.5 4.8 (0.15, 0.18) 359 Example 25 Compound 77 4.2 4.9 (0.15, 0.18) 420 Example 26 Compound 79 4.6 4.6 (0.15, 0.17) 490 Example 27 Compound 82 4.5 4.6 (0.15, 0.18) 358 Example 28 Compound 83 4.4 4.7 (0.15, 0.19) 344 Example 29 Compound 88 4.2 4.8 (0.15, 0.17) 406 Example 30 Compound 101 4.7 4.6 (0.15, 0.17) 366 Example 31 Compound 116 4.4 4.9 (0.15, 0.18) 389 Example 32 Compound 117 4.7 4.7 (0.15, 0.18) 419 Example 33 Compound 119 4.7 5.1 (0.15, 0.19) 477 Example 34 Compound 122 4.3 4.8 (0.15, 0.18) 378 Example 35 Compound 123 4.4 4.7 (0.15, 0.19) 369 Example 36 Compound 127 4.3 4.6 (0.15, 0.17) 345 Example 37 Compound 128 4.3 4.7 (0.15, 0.17) 372 Example 38 Compound 138 4.6 4.6 (0.15, 0.18) 335 Example 39 Compound 157 4.5 4.7 (0.15, 0.18) 354 Example 40 Compound 185 4.7 4.6 (0.15, 0.18) 341 Example 41 Compound 11 4.6 4.6 (0.15, 0.17) 339 Example 42 Compound 19 4.5 4.8 (0.15, 0.18) 390 Example 43 Compound 23 4.6 5.0 (0.15, 0.18) 339 Example 44 Compound 246 4.1 4.8 (0.15, 0.17) 402 Example 45 Compound 97 4.7 4.6 (0.15, 0.17) 347 Example 46 Compound 534 4.2 4.9 (0.15, 0.17) 398 Example 47 Compound 169 4.5 4.7 (0.15, 0.18) 368 Example 48 Compound 172 4.7 4.6 (0.15, 0.19) 346 Example 49 Compound 173 4.6 4.6 (0.15, 0.17) 354 Example 50 Compound 188 4.6 4.5 (0.15, 0.17) 336 Example 51 Compound 18 4.6 4.8 (0.15, 0.18) 376 Example 52 Compound 20 4.7 4.9 (0.15, 0.18) 379 Example 53 Compound 153 4.5 5.0 (0.15, 0.18) 487

As shown in the results of Table 3, when the device was manufactured from the electron transport layer materials used in Examples 1 to 53 in the present invention in comparison with the electron transport layer material E1 used in Comparative Example 1, lifetime was increased and driving voltage and efficiency Is improved.

Claims (13)

A heterocyclic compound represented by the following formula (1):
[Chemical Formula 1]
Figure pat00077

In Formula 1,
At least one of X1 and X2 is N and the remainder is N or CR1,
At least one of R1 to R15 is - (L) p- (Y) q, and the others are the same or different, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C 1 to C 60 straight or branched alkyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkenyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkynyl group; A substituted or unsubstituted C 1 to C 60 straight or branched chain alkoxy group; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heterocycloalkyl group; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; -SiRR'R "; -P (= O) RR '; and C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups, or substituted or unsubstituted C 2 Or an amine group substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having a carbon number of 1 to 60 , or two or more adjacent groups of R1 to R15 are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aliphatic or aromatic hydrocarbon ring Lt; / RTI &gt;
L is a direct bond; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic arylene group; And a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroarylene group,
Y is hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C 1 to C 60 straight or branched alkyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkenyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkynyl group; A substituted or unsubstituted C 1 to C 60 straight or branched chain alkoxy group; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heterocycloalkyl group; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; -SiRR'R "; -P (= O) RR '; and C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups, or substituted or unsubstituted C 2 And an amine group substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having a carbon number of 1 to 60 ,
A substituted or unsubstituted C 1 to C 60 linear or branched alkyl group, a substituted or unsubstituted C 3 to C 60 linear or branched alkyl group, a substituted or unsubstituted C 3 to C alkenyl group, C 60 monocyclic or polycyclic cycloalkyl group; or a substituted or unsubstituted C 2 to monocyclic or polycyclic heteroaryl group of C 60 group, a; substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups,
p is an integer of 0 to 10, q is an integer of 1 to 10,
When two or more L and Y are present, they are each independently the same or different from each other. The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following formulas 2 to 4:
(2)
Figure pat00078

(3)
Figure pat00079

[Chemical Formula 4]
Figure pat00080

In the above Formulas 2 to 4, the definitions of R 1 to R 15 are the same as those in Formula 1. The compound according to claim 1, wherein R1 to R15 in the formula (1) are - (L) p- (Y) q,
And the others are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; -CN; A substituted or unsubstituted C 1 to C 60 straight or branched alkyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkenyl group; A substituted or unsubstituted C 2 to C 60 linear or branched alkynyl group; A substituted or unsubstituted C 1 to C 60 straight or branched chain alkoxy group; A substituted or unsubstituted C 3 to C 60 monocyclic or polycyclic cycloalkyl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heterocycloalkyl group; A substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; ? -SiRR R "; -P (= O) RR ?; and C 1 to C 20 alkyl group, a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups, or substituted or unsubstituted C 2 And an amine group substituted or unsubstituted with a monocyclic or polycyclic heteroaryl group having a carbon number of 1 to 60. [ [2] The heterocyclic compound of claim 1, wherein R1 to R15 in Formula 1 are - (L) p- (Y) q, and all others are hydrogen. The compound according to claim 1, wherein R1 in the formula (1) is - (L) p- (Y) q,
L is a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic arylene group; And a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroarylene group,
Y is a substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group; A substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group; And substituted or unsubstituted C 1 to C 20 alkyl groups, substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl groups, or substituted or unsubstituted C 2 to C 60 mono- or polycyclic heteroaryl groups, A heterocyclic group, and a substituted or unsubstituted amino group. [2] The compound according to claim 1, wherein the "substituted or unsubstituted" A halogen group; -CN; A C 1 to C 60 straight or branched alkyl group; A C 2 to C 60 straight or branched chain alkenyl group; A C 2 to C 60 linear or branched alkynyl group; A C 3 to C 60 monocyclic or polycyclic cycloalkyl group; A C 2 to C 60 monocyclic or polycyclic heterocycloalkyl group; A C 6 to C 60 monocyclic or polycyclic aryl group; A C 2 to C 60 monocyclic or polycyclic heteroaryl group; -SiR ' R &quot;; -P (= O) RR '; C 1 to C 20 alkylamine groups; A C 6 to C 60 monocyclic or polycyclic arylamine group; And a monocyclic or polycyclic heteroarylamine group having a carbon number of 2 to 60 , or substituted or unsubstituted with a substituent having two or more of the substituents bonded thereto, or two Wherein said substituent is substituted or unsubstituted with a substituent connected thereto. The method of claim 1,
Figure pat00081
X3 and X4 are substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic aromatic heterocyclic ring. The method of claim 7,
Figure pat00082
Is a heterocyclic compound represented by any one of the following structural formulas:
Figure pat00083
Figure pat00084
Figure pat00085

Figure pat00086
Figure pat00087
Figure pat00088

In the above structural formulas, Z 1 to Z 3 are the same or different from each other and are each independently S or O,
Z &lt; 4 &gt; to Z &lt; 9 &gt; are the same or different from each other and each independently CR &
R 'and R "are the same or different and each independently hydrogen, substituted or unsubstituted C 1 to C 60 linear or branched alkyl, or substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic It is the aryl of the circle. The heterocyclic compound according to claim 1, wherein the formula 1 is represented by any one of the following compounds:
Figure pat00089

Figure pat00090

Figure pat00091


Figure pat00093

Figure pat00094

Figure pat00095

Figure pat00096

Figure pat00097

Figure pat00098

Figure pat00099

Figure pat00100

Figure pat00101

Figure pat00102

Figure pat00103

Figure pat00104

Figure pat00105

Figure pat00106

Figure pat00107

Figure pat00108

Figure pat00109

Figure pat00110

Figure pat00111

Figure pat00112

Figure pat00113

Figure pat00114

Figure pat00115

Figure pat00116

Figure pat00117

Figure pat00118

Figure pat00119

Figure pat00120

Figure pat00121

Figure pat00122

Figure pat00123

Figure pat00124

Figure pat00125

Figure pat00126

Figure pat00127

Figure pat00128
 1. An organic light emitting device comprising an anode, a cathode, and at least one organic layer provided between the anode and the cathode, wherein at least one of the organic layers includes a heterocyclic compound according to any one of claims 1 to 9. The organic EL device according to claim 10, wherein the organic material layer includes at least one of a hole blocking layer, an electron injecting layer and an electron transporting layer, and at least one of the hole blocking layer, the electron injecting layer and the electron transporting layer includes the heterocyclic compound Wherein the organic light-emitting device comprises: [Claim 11] The organic light emitting device of claim 10, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the heterocyclic compound. [Claim 11] The organic electroluminescent device according to claim 10, wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, wherein one of the layers includes the heterocyclic compound .
KR1020150092432A 2015-06-29 2015-06-29 Hetero-cyclic compound and organic light emitting device using the same KR20170002208A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020150092432A KR20170002208A (en) 2015-06-29 2015-06-29 Hetero-cyclic compound and organic light emitting device using the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020150092432A KR20170002208A (en) 2015-06-29 2015-06-29 Hetero-cyclic compound and organic light emitting device using the same

Publications (1)

Publication Number Publication Date
KR20170002208A true KR20170002208A (en) 2017-01-06

Family

ID=57832611

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020150092432A KR20170002208A (en) 2015-06-29 2015-06-29 Hetero-cyclic compound and organic light emitting device using the same

Country Status (1)

Country Link
KR (1) KR20170002208A (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4356429A (en) 1980-07-17 1982-10-26 Eastman Kodak Company Organic electroluminescent cell

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4356429A (en) 1980-07-17 1982-10-26 Eastman Kodak Company Organic electroluminescent cell

Similar Documents

Publication Publication Date Title
US11387418B2 (en) Organic light emitting element and composition for organic material layer in organic light emitting element
KR101739024B1 (en) Organic light emitting device and composition for organic layer of organic light emitting device
JP6799174B2 (en) Organic light emitting device and composition for organic material layer of organic light emitting device
KR102266693B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR101882221B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR101952324B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR102589217B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR20170064379A (en) Hetero-cyclic compound and organic light emitting device using the same
KR101946020B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR101838693B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR20180005533A (en) Hetero-cyclic compound and organic light emitting device using the same
US20220340550A1 (en) Organic light-emitting device, method for manufacturing same, and composition for organic material layer of organic light-emitting device
JP2020535185A (en) Heterocyclic compounds and organic light emitting devices containing them
JP7421802B2 (en) Heterocyclic compounds and organic light-emitting devices containing them
KR20180060474A (en) Hetero-cyclic compound and organic light emitting device using the same
US20230292599A1 (en) Heterocyclic compound, organic light-emitting device comprising same, and composition for organic material layer of organic light-emitting device
KR20140070425A (en) New compounds and organic electronic device using the same
KR102180744B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR101947622B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR20180071609A (en) Hetero-cyclic compound and organic light emitting device using the same
KR20190064256A (en) Compound and organic light emitting device comprising the same
KR102589223B1 (en) Hetero-cyclic compound and organic light emitting device using the same
KR102626318B1 (en) Compound and organic light emitting device using the same
KR20170004432A (en) Hetero-cyclic compound and organic light emitting device using the same
KR20190064236A (en) Compound and organic light emitting device comprising the same