Organic electroluminescent device

Abstract

The present disclosure relates to an organic electroluminescent device including a compound represented by Formula 1, and an organic electroluminescent device having a plurality of light-emitting layers can be provided, which is superior in driving voltage, luminous efficiency, external quantum efficiency, and / or color coordinate characteristics as compared with a conventional organic electroluminescent device.

Description

Technical Field

[0001] The present disclosure relates to an organic electroluminescent device including an organic electroluminescent compound. Background Art

[0002] An electroluminescent (EL) device is a self-luminous device, and its advantages are that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. The organic EL device was first developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and an aluminum complex as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].[[]]END]]

[0003] A white organic electroluminescent device uses a technique of achieving white light by mixing light-emitting materials of various wavelengths. To achieve white, a light-emitting layer containing materials having blue (B) and yellow-green (YG) wavelengths or materials having blue (B), red (R), and green (G) wavelengths is used. The light-emitting characteristics can be adjusted according to the light-emitting layer structure. According to the structure of the light-emitting layer, the organic electroluminescent device can be classified into a single light-emitting layer (single EML), multiple light-emitting layers (multiple EMLs), and a tandem structure in which devices are stacked, etc.

[0004] A tandem organic electroluminescent device (corresponding to currently commercialized technologies) is a structure in which two or more independent OLED devices are connected in series. This has the following advantages: Each OLED device is combined with a charge generation layer to individually optimize the unit OLED device, so that the control of luminous efficiency and color is easy. In addition, in a tandem organic electroluminescent device, the individual OLED devices are driven with the same amount of current, and the luminance and current efficiency at the same current can be multiplied by the number of connected OLED devices. Therefore, tandem organic electroluminescent devices are currently mainly used as technologies for mass-producing OLED TVs.

[0005] Korean Patent Application Publication No. 2010-0072644 discloses an embodiment of an organic electroluminescent device for improving the color stability of a blue light-emitting layer. However, there is still a need to improve the following characteristics of the OLED device: luminous efficiency, quantum efficiency, and / or color coordinates. Summary of the Invention

[0006] Technical Problem

[0007] An object of the present disclosure is to provide an organic electroluminescent device having multiple light-emitting layers, which is superior in terms of driving voltage, luminous efficiency, external quantum efficiency, and / or color coordinate characteristics compared to conventional organic electroluminescent devices.

[0008] Solution to the Problem

[0009] The inventors of the present invention have found that an organic electroluminescent device comprising a compound of the present disclosure can improve charge recombination efficiency and increase red light emission, thereby improving external quantum efficiency. Specifically, the above object can be achieved by an organic electroluminescent device comprising an anode, a cathode, and a plurality of light-emitting layers between the anode and the cathode, wherein at least one of the plurality of light-emitting layers comprises a compound represented by Formula 1:

[0010]

[0011] wherein

[0012] M represents O or S;

[0013] X1 to X 12 each independently represents N or CR1;

[0014] La represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group;

[0015] Ar and R1 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino group; or two or more adjacent Ars may be connected to each other to form one or more rings, and two or more adjacent R1s may be connected to each other to form one or more rings; wherein if there are multiple R1s, each R1 may be the same or different; and

[0016] a represents an integer of 1 or 2, wherein if a is the integer 2, each Ar may be the same or different.

[0017] Advantages of the present invention

[0018] According to the present disclosure, an organic electroluminescent device is provided that has a plurality of light-emitting layers and is superior in terms of driving voltage, luminous efficiency, external quantum efficiency, and / or color coordinate characteristics compared to conventional organic electroluminescent devices, and a display system or a lighting system can be manufactured using the organic electroluminescent device. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] Figure 1 Schematically shows the structure of an organic electroluminescent device according to an embodiment of the present disclosure.

[0020] Figure 2 Shows a representative formula of the compound represented by Formula 1 according to the present disclosure.

[0021] Figure 3 Shows the intensity according to wavelength of the organic electroluminescent devices produced in Comparative Example 1 and Device Examples 2 to 4.

[0022] Figure 4 Shows the intensity according to wavelength of the organic electroluminescent devices produced in Comparative Example 1 and Device Examples 5 to 7. DETAILED DESCRIPTION

[0023] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and does not mean to limit the scope of the present disclosure in any way.

[0024] The compound represented by Formula 1 will be described in more detail as follows.

[0025] In Formula 1, M represents O or S.

[0026] In Formula 1, X1 to X 12 each independently represents N or CR1. According to an embodiment of the present disclosure, X1 to X 12 may all represent CR1. According to another embodiment of the present disclosure, any one of X1 to X 12 may represent N. According to another embodiment of the present disclosure, any two of X1 to X 12 may represent N.

[0027] In Formula 1, a represents an integer of 1 or 2, where if a is the integer 2, each Ar may be the same or different.

[0028] In Formula 1, La represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group; preferably a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (5- to 25-membered) heteroarylene group; and more preferably a single bond, an unsubstituted (C6-C18) arylene group, or an unsubstituted (5- to 18-membered) heteroarylene group. The heteroarylene group may include at least one of nitrogen, oxygen, and sulfur; and preferably may include at least one of nitrogen and sulfur. For example, La may represent a single bond, a phenylene group, a naphthylene group, a biphenylene group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an isoquinolyl group, a quinazolinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoxazolinyl group, an indoloquinoxalinyl group, a benzothienopyrimidinyl group, a pyridopyrazinyl group, or a benzquinazolinyl group.

[0029] In Formula 1, Ar and R1 each independently represent hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino group; or two or more adjacent Ar may be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C30) alicyclic ring or aromatic ring, or a combination thereof, and two or more adjacent R1 may be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C30) alicyclic ring or aromatic ring, or a combination thereof, and one or more carbon atoms in the alicyclic ring or aromatic ring, or a combination thereof, may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur.

[0030] Preferably, Ar can represent a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (5- to 25-membered) heteroaryl group, a substituted or unsubstituted bis(C6-C25)arylamino group, or a substituted or unsubstituted (C6-C25)aryl(5- to 25-membered)heteroarylamino group. More preferably, Ar can represent an unsubstituted or (C6-C18)aryl group substituted with at least one of deuterium, (C1-C10)alkyl, and (C6-C18)aryl; a (5- to 25-membered) heteroaryl group that is unsubstituted or substituted with at least one of (C1-C10)alkyl and (C6-C12)aryl; a bis(C6-C25)arylamino group that is unsubstituted or substituted with one or more (C1-C6)alkyl groups; or an unsubstituted (C6-C18)aryl(5- to 25-membered)heteroarylamino group. According to one embodiment of the present disclosure, Ar can represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted triazolopyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted benzothienopyrimidinyl group, a substituted or unsubstituted acenaphthopyrimidinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted dibenzoquinoxalinyl group, a substituted or unsubstituted indoloquinoxalinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted benzothienopyridyl group, a substituted or unsubstituted benzofuropyridyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzothiazolinyl group, a substituted or unsubstituted phenanthrimidazolyl group, a substituted or unsubstituted diphenylamino group, a substituted or unsubstituted phenylbiphenylamino group, a substituted or unsubstituted fluorenylphenylamino group, a substituted or unsubstituted dibenzothienylphenylamino group, or a substituted or unsubstituted dibenzofuranylphenylamino group.According to another embodiment of the present disclosure, Ar may represent an aryl group that is unsubstituted or substituted by at least one of deuterium and naphthyl; an unsubstituted naphthyl group; an unsubstituted biphenyl group; an unsubstituted terphenyl group; a fluorene group substituted by one or more methyl groups; an unsubstituted fluoranthenyl group; a triazine group that is unsubstituted or substituted by at least one of phenyl and naphthyl; a pyridyl group that is unsubstituted or substituted by one or more phenyl groups; a triazolopyridyl group substituted by one or more phenyl groups; a pyrimidine group that is unsubstituted or substituted by one or more phenyl groups; a quinazoline group substituted by one or more phenyl groups; an isoquinoline group substituted by one or more phenyl groups; a carbazole group that is unsubstituted or substituted by one or more phenyl groups; an unsubstituted dibenzothiophene group; a dibenzofuran group that is unsubstituted or substituted by one or more phenyl groups; a naphthyridine group substituted by one or more phenyl groups; an unsubstituted diphenylamino group; an unsubstituted phenylbiphenylamino group; a dimethylfluorenylphenylamino group; a benzothienopyrimidine group substituted by one or more phenyl groups; an unsubstituted benzothienoquinoline group; an unsubstituted benzofuroquinoline group; a benzquinazoline group substituted by one or more phenyl groups; a benzothiazoline group substituted by one or more phenyl groups; a quinoxaline group substituted by one or more phenyl groups; a benzquinoxaline group substituted by one or more phenyl groups; an unsubstituted dibenzoquinoxaline group; an indoloquinoxaline group substituted by one or more phenyl groups; a phenanthrimidazole group substituted by one or more phenyl groups; an unsubstituted dibenzothiophenyphenylamino group; an unsubstituted dibenzofuranphenylamino group; a nitrogen-containing (17-membered) heteroaryl group substituted by one or more methyl groups; a (25-membered) heteroaryl group containing nitrogen and oxygen; or an acenapthyrimidine group substituted by one or more phenyl groups.

[0031] Preferably, R1 may represent hydrogen, a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (3- to 25-membered) heteroaryl; or two or more adjacent R1s may be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C25) alicyclic ring or aromatic ring, or a combination thereof, and one or more carbon atoms of the alicyclic ring or aromatic ring, or the combination thereof, may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur. More preferably, R1 may represent hydrogen, a substituted or unsubstituted (C6-C18) aryl, or a substituted or unsubstituted (5- to 18-membered) heteroaryl; or two or more adjacent R1s may be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C18) aromatic ring, and one or more carbon atoms of the aromatic ring may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur. Even more preferably, R1 may represent hydrogen; a (C6-C12) aryl that is unsubstituted or substituted by one or more (5- to 18-membered) heteroaryls; or a (5- to 13-membered) heteroaryl that is unsubstituted or substituted by one or more (C6-C18) aryls; or two or more adjacent R1s may be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C10) aromatic ring, and one or more carbon atoms of the aromatic ring may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur. For example, R1 may represent hydrogen; a phenyl that is unsubstituted or substituted by one or more diphenyltriazinyl groups; diphenyltriazinyl; a quinazolinyl substituted by one or more phenyl groups; or an unsubstituted pyridyl; or two adjacent R1s may be connected to each other to form an unsubstituted benzene ring, an indene ring substituted by at least one of methyl and phenyl, an unsubstituted pyridine ring, an unsubstituted benzothiophene ring, an unsubstituted benzofuran ring, or an indole ring substituted by one or more phenyl groups or one or more phenylquinoxalinyl groups. If there are multiple R1s, each R1 may be the same or different.

[0032] According to one embodiment of the present disclosure, in Formula 1, at least two adjacent ones of X1 to X 12 are CR1, and two adjacent R1s may be fused into any one of Formulas 2 to 6 to form one or more rings. One or more rings may be formed in a compound represented by Formula 1. For example, the ring may be fused with the benzene ring of the skeleton to form a dibenzothiophene ring, a dibenzofuran ring, a naphthalene ring, a fluorene ring, or a substituted or unsubstituted carbazole ring.

[0033]

[0034]

[0035] In Formulas 2 to 6, represents the connection site of C and R1 in CR1.

[0036] In Formula 4, X represents N or CH. According to one embodiment of the present disclosure, X can all represent CH. According to another embodiment of the present disclosure, any one of X can represent N.

[0037] In Formula 5, R2 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino. Preferably, R2 represents substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-membered to 25-membered) heteroaryl. More preferably, R2 represents unsubstituted (C6-C18) aryl, or unsubstituted or substituted by one or more (C6-C18) aryl groups (5-membered to 18-membered) heteroaryl. For example, R2 can represent unsubstituted phenyl, or quinoxalinyl substituted by one or more phenyl groups.

[0038] In Formula 6, R 11 and R 12 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-membered to 30-membered) heteroaryl, or substituted or unsubstituted (C3-C30) cycloalkyl; or R 11 and R 12 can be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (C3-C30) alicyclic ring or aromatic ring, or a combination thereof, and one or more carbon atoms of the alicyclic ring or aromatic ring, or a combination thereof, can be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur. Preferably, R 11 and R 12 each independently represent hydrogen, substituted or unsubstituted (C1-C6) alkyl, or substituted or unsubstituted (C6-C12) aryl; or R 11 and R 12 can be connected to each other to form a substituted or unsubstituted, monocyclic or polycyclic (C5-C10) alicyclic ring or aromatic ring, or a combination thereof. More preferably, R 11 and R 12each independently represents hydrogen, unsubstituted (C1-C6) alkyl, or unsubstituted (C6-C12) aryl; or R 11 and R 12 may be connected to each other to form a spiro ring. For example, R 11 and R 12 each independently represents hydrogen, methyl, or phenyl. R 11 and R 12 may be the same or different. According to one embodiment of the present disclosure, R 11 and R 12 may be the same.

[0039] In the present disclosure, (hetero)aryl or heterocycloalkyl may each independently contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably at least one heteroatom selected from N, O, and S. In addition, the heteroatom may be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.

[0040] The compound represented by Formula 1 may be represented by any one of Formulas 7 to 10 below.

[0041]

[0042] In Formulas 7 to 10, X1 to X 12 and M are as defined in Formula 1 above.

[0043] As used herein, the term “(C1-C30) (sub)alkyl” means a straight-chain or branched-chain (sub)alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above-mentioned alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. The term “(C2-C30) alkenyl” means a straight-chain or branched-chain alkenyl having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above-mentioned alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term “(C2-C30) alkynyl” means a straight-chain or branched-chain alkynyl having 2 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above-mentioned alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term “(C3-C30) (sub)cycloalkyl” means a monocyclic hydrocarbon or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above-mentioned cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term “(3- to 7-membered) heterocycloalkyl” means a cycloalkyl having 3 to 7, preferably 5 to 7, ring skeleton atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably consisting of the group of O, S, and N. The above-mentioned heterocycloalkyl may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran, etc. The term “(C6-C30) (sub)aryl” means a monocyclic or fused-ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, wherein the number of ring skeleton carbon atoms is preferably 6 to 25, more preferably 6 to 18. The above-mentioned aryl may be partially saturated and may contain a spiro structure. The above-mentioned aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, yl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. More specifically, the aryl may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, benzoanthracenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, 1- yl, 2- yl, 3- yl, 4- yl, 5- yl, 6- base, benzo[c]phenanthryl, benzo[g] base, 1-benzo[c]phenanthryl, 2-benzo[c]phenanthryl, 3-benzo[c]phenanthryl, 4-benzo[c]phenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, o-terphenyl-4-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-quaterphenyl-4-yl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl-4-yl, 4''-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, etc.

[0044] The term “(3- to 30-membered)(hetero)aryl” is an aryl or heteroaryl having 3 to 30 ring backbone atoms and containing at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above (hetero)aryl can be monocyclic or a fused ring condensed with at least one benzene ring; it can be partially saturated; it can be a (hetero)aryl formed by connecting at least one heteroaryl or aryl to a heteroaryl via one or more single bonds; and it can contain a spiro structure. The above heteroaryl can include monocyclic heteroaryls such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc.; and fused ring heteroaryls such as benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, etc. More specifically, the heteroaryl can include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl, 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl, 7-imidazopyridyl, 8-imidazopyridyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuryl, 4-isobenzofuryl, 5-isobenzofuryl, 6-isobenzofuryl, 7-isobenzofuryl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl,8 - isoquinolinyl, 2 - quinoxalinyl, 5 - quinoxalinyl, 6 - quinoxalinyl, 1 - carbazolyl, 2 - carbazolyl, 3 - carbazolyl, 4 - carbazolyl, 9 - carbazolyl, azacarbazol - 1 - yl, azacarbazol - 2 - yl, azacarbazol - 3 - yl, azacarbazol - 4 - yl, azacarbazol - 5 - yl, azacarbazol - 6 - yl, azacarbazol - 7 - yl, azacarbazol - 8 - yl, azacarbazol - 9 - yl, 1 - phenanthridinyl, 2 - phenanthridinyl, 3 - phenanthridinyl, 4 - phenanthridinyl, 6 - phenanthridinyl, 7 - phenanthridinyl, 8 - phenanthridinyl, 9 - phenanthridinyl, 10 - phenanthridinyl, 1 - acridinyl, 2 - acridinyl, 3 - acridinyl, 4 - acridinyl, 9 - acridinyl, 2 - oxazolyl, 4 - oxazolyl, 5 - oxazolyl, 2 - oxadiazolyl, 5 - oxadiazolyl, 3 - furazanyl, 2 - thienyl, 3 - thienyl, 2 - methylpyrrol - 1 - yl, 2 - methylpyrrol - 3 - yl, 2 - methylpyrrol - 4 - yl, 2 - methylpyrrol - 5 - yl, 3 - methylpyrrol - 1 - yl, 3 - methylpyrrol - 2 - yl, 3 - methylpyrrol - 4 - yl, 3 - methylpyrrol - 5 - yl, 2 - tert - butylpyrrol - 4 - yl, 3-(2 - phenylpropyl)pyrrol - 1 - yl, 2 - methyl - 1 - indolyl, 4 - methyl - 1 - indolyl, 2 - methyl - 3 - indolyl, 4 - methyl - 3 - indolyl, 2 - tert - butyl - 1 - indolyl, 4 - tert - butyl - 1 - indolyl, 2 - tert - butyl - 3 - indolyl, 4 - tert - butyl - 3 - indolyl, 1 - dibenzofuranyl, 2 - dibenzofuranyl, 3 - dibenzofuranyl, 4 - dibenzofuranyl, 1 - dibenzothiophenyl, 2 - dibenzothiophenyl, 3 - dibenzothiophenyl, 4 - dibenzothiophenyl, 1 - silylfluorenyl, 2 - silylfluorenyl, 3 - silylfluorenyl, 4 - silylfluorenyl, 1 - germylfluorenyl, 2 - germylfluorenyl, 3 - germylfluorenyl, 4 - germylfluorenyl, etc. "Halogen" includes F, Cl, Br, and I.

[0045] In addition, "ortho (o -)", "meta (m -)", and "para (p -)" are prefixes that indicate the relative positions of substituents, respectively. Ortho indicates that two substituents are adjacent to each other, and for example, when two substituents in a benzene derivative occupy positions 1 and 2, it is called ortho. Meta indicates that two substituents are at positions 1 and 3, and for example, when two substituents in a benzene derivative occupy positions 1 and 3, it is called meta. Para indicates that two substituents are at positions 1 and 4, and for example, when two substituents in a benzene derivative occupy positions 1 and 4, it is called para.

[0046] As used herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or another functional group (i.e., a substituent). In the present disclosure, the substituents of the substituted (C1-C30) (sub)alkyl, substituted (C6-C30) (sub)aryl, substituted (3- to 30-membered) (sub)heteroaryl, substituted (C3-C30) (sub)cycloalkyl, substituted (C1-C30) alkoxy, substituted tris(C1-C30) alkylsilyl, substituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted (C1-C30) alkyldi(C6-C30) arylsilyl, substituted tris(C6-C30) arylsilyl, substituted mono- or di-(C1-C30) alkylamino, substituted mono- or di-(C6-C30) arylamino, substituted (C1-C30) alkyl(C6-C30) arylamino, and the substituted (C6-C30) aryl(3- to 30-membered) heteroarylamino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30) alkyl; halo(C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; unsubstituted or (3- to 30-membered) heteroaryl substituted with one or more (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with one or more (3- to 30-membered) heteroaryl; tris(C1-C30) alkylsilyl; tris(C6-C30) arylsilyl; di(C1-C30) alkyl(C6-C30) arylsilyl; (C1-C30) alkyldi(C6-C30) arylsilyl; amino; mono- or di-(C1-C30) alkylamino; mono- or di-(C6-C30) arylamino unsubstituted or substituted with one or more (C1-C30) alkyl; (C1-C30) alkyl(C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di(C6-C30) arylboronyl; di(C1-C30) alkylboronyl; (C1-C30) alkyl(C6-C30) arylboronyl; (C6-C30) aryl(C1-C30) alkyl; and (C1-C30) alkyl(C6-C30) aryl. According to one embodiment of the present disclosure, the substituents are each independently at least one selected from the group consisting of: deuterium; (C1-C20) alkyl; unsubstituted (C6-C25) aryl; and unsubstituted or (5- to 25-membered) heteroaryl substituted with one or more (C6-C25) aryl.According to another embodiment of the present disclosure, each substituent is independently at least one selected from the group consisting of: deuterium; (C1-C10) alkyl; unsubstituted (C6-C18) aryl; and (5- to 18-membered) heteroaryl substituted with one or more (C6-C18) aryl groups. For example, each substituent may independently be at least one selected from the group consisting of: deuterium, methyl, phenyl, naphthyl, diphenyltriazinyl, and phenylquinoxalinyl.

[0047] The compound represented by Formula 1 may be specifically exemplified by the following compounds, but is not limited thereto.

[0048]

[0049]

[0050]

[0051] s

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] The compound represented by Formula 1 according to the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by Formula 1 can be prepared by referring to the following Reaction Schemes 1 to 9, but is not limited thereto.

[0062] [Reaction Scheme 1]

[0063]

[0064] [Reaction Scheme 2]

[0065]

[0066] [Reaction Scheme 3]

[0067]

[0068] [Reaction Scheme 4]

[0069]

[0070] [Reaction Scheme 5]

[0071]

[0072] [Reaction Scheme 6]

[0073]

[0074] [Reaction Scheme 7]

[0075]

[0076] [Reaction Scheme 8]

[0077]

[0078]

[0079] [Reaction Scheme 9] ))

[0080]

[0081] In Reaction Schemes 1 to 9, X1 to X 12 , R1, La, Ar, and a are each as defined in Formula 1; R2, R 11 and R 12 are each as defined in Formulas 5 and 6; Z is as defined in R1; and OTf is trifluoromethanesulfonate.

[0082] Although the illustrative synthetic examples of the compounds represented by Formula 1 are described above, those skilled in the art will be able to readily understand that all illustrative synthetic examples are based on Buchwald-Hartwig cross-coupling reactions, N-arylation reactions, acidified montmorillonite (H-mont)-mediated etherification reactions, Miyaura borylation reactions, Suzuki cross-coupling reactions, intramolecular acid-induced cyclization reactions, Pd(II)-catalyzed oxidative cyclization reactions, Grignard reactions, Heck reactions, cyclic dehydration reactions, SN1 substitution reactions, SN2 substitution reactions, phosphine-mediated reductive cyclization reactions, etc., and that even when substituents defined in Formula 1 above but not specified in the specific synthetic examples are bonded, the above reactions proceed.

[0083] Hereinafter, the preparation methods and characteristics of the compounds according to the present disclosure will be explained in detail. However, the present disclosure is not limited to the following examples.

[0084] Example 1: Preparation of Compound C-8

[0085]

[0086] Synthesis of Compound 1

[0087] In a flask, 70 g of 2-nitro-1-naphthol (370 mmol) and 4.5 g of 4-dimethylaminopyridine (DMAP) (37 mmol) were dissolved in 1800 mL of dichloromethane (MC). 62 mL of triethylamine (TEA) (444 mmol) was added dropwise to the mixture at 0 °C and stirred for 20 minutes. 125.3 g of trifluoromethanesulfonic anhydride (Tf2O) (444 mmol) was slowly added dropwise to the reaction mixture at the same temperature and stirred for 1 hour. After completion of the reaction, the organic layer was extracted with MC and the residual moisture was removed using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 96.2 g of Compound 1 (yield: 81%).

[0088] Synthesis of Compound 2

[0089] In a flask, 96.2 g of Compound 1 (299 mmol), 72.1 g of 2-bromophenylboronic acid (359 mmol), 17.3 g of tetrakis(triphenylphosphine)palladium(0) (15 mmol), and 79.3 g of sodium carbonate (749 mmol) were dissolved in 1400 mL of toluene, 350 mL of ethanol, and 350 mL of water, and the mixture was refluxed for 1 hour. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 98 g of Compound 2 (yield: 99%).

[0090] Synthesis of Compound 3

[0091] In a flask, 98 g of Compound 2 (299 mmol), 78.5 g of 2-aminophenylboronic acid pinacol ester (358 mmol), 17.2 g of tetrakis(triphenylphosphine)palladium(0) (15 mmol), and 103 g of potassium carbonate (747 mmol) were dissolved in 1300 mL of toluene, 350 mL of ethanol, and 350 mL of water, and the mixture was refluxed for 20 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 54 g of Compound 3 (yield: 53%).

[0092] Synthesis of Compound 4

[0093] In a flask, 25 g of Compound 3 (73 mmol) was dissolved in 250 mL of acetic acid and 25 mL of sulfuric acid. 6.5 g of sodium nitrite (95 mmol) was slowly added dropwise to the mixture at 0 °C and stirred for 40 minutes. After the reaction was completed, the reaction mixture was added dropwise to water and filtered to remove the moisture. Thereafter, the residue was dried and separated by column chromatography to obtain 2 g of Compound 4 (yield: 8.4%).

[0094] Synthesis of Compound 5

[0095] In a flask, 4.7 g of Compound 4 (15 mmol) was dissolved in 48 mL of triethyl phosphite and 48 mL of 1,2-dichlorobenzene, and the mixture was refluxed for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 2.7 g of Compound 5 (yield: 63%).

[0096] Synthesis of Compound C-8

[0097] In a flask, 2.1 g of Compound 5 (7 mmol), 3.1 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (8 mmol), 0.81 g of palladium(II) acetate (0.36 mmol), 0.3 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (0.7 mmol), and 1.7 g of sodium tert-butoxide (NaOtBu) (18 mmol) were dissolved in 72 mL of 1,2-xylene, and the mixture was refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 2.5 g of Compound C-8 (yield: 58%).

[0098] Compound MW UV PL M.P. Tg C-8 598.71 308nm 495nm 285℃ 132.37℃

[0099] Example 2: Preparation of Compound C-301

[0100]

[0101] In a flask, 5.0 g of Compound 5 (17 mmol), 7.08 g of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (21 mmol), 105 mg of DMAP (0.858 mmol), and 7.1 g of potassium carbonate (51 mmol) were dissolved in 85 mL of dimethylformamide (DMF), and the mixture was refluxed for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 4.8 g of Compound C-301 (yield: 47%).

[0102] 1 H NMR (600 MHz, CDCl3) 9.09 - 9.07 (d, J = 12 Hz, 1H), 8.93 - 8.91 (d, J = 12 Hz, 1H), 8.74 - 8.73 (d, J = 6 Hz, 2H), 8.71 - 8.69 (d, J = 12 Hz, 2H), 7.80 - 7.75 (m, 6H), 7.73 - 7.69 (m, 3H), 7.64 - 7.57 (m, 3H), 7.52 - 7.38 (m, 8H)

[0103] Compound MW Tg M.P. C-301 598.71 124.4℃ 236℃

[0104] Example 3: Preparation of Compound C-10

[0105]

[0106] In a flask, 5.0 g of compound 5 (17 mmol), 11.28 g of 2-(4-bromonaphthalen-1-yl)-4,6-diphenyl-1,3,5-triazine (21 mmol), 625 mg of tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (0.686 mmol), 565 mg of SPhos (1 mmol), and 4.9 g of sodium tert-butoxide (51 mmol) were dissolved in 100 mL of o-xylene, and the mixture was refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 3.6 g of compound C-10 (yield: 32%).

[0107] 1 H NMR (600 MHz, CDCl3) 9.25 - 9.24 (d, J = 6 Hz, 1H), 8.85 - 8.83 (sd, J = 12 Hz, 4H), 8.68 - 8.67 (d, J = 6 Hz, 1H), 7.94 - 7.92 (m, 1H), 7.82 - 7.79 (m, 3H), 7.74 - 7.61 (m, 10H), 7.49 - 7.42 (m, 5H), 7.31 - 7.29 (t, J = 6 Hz, 1H), 7.16 - 7.15 (d, J = 6 Hz, 1H), 6.96 - 6.94 (d, J = 12 Hz, 1H)

[0108] Compound MW Tg M.P. C-10 648.7 159.5℃ 176℃

[0109] Example 4: Preparation of Compound C-7

[0110]

[0111] In a flask, 5 g of compound 5 (17.1 mmol), 5.5 g of 2-chloro-4,6-diphenyl-1,3,5-triazine (20.5 mmol), 0.1 g of DMAP (0.85 mmol), and 7.1 g of potassium carbonate (51.4 mmol) were dissolved in 85 mL of DMF, and the mixture was refluxed for 3 hours. After completion of the reaction, the reaction mixture was cooled, and methanol and water were added thereto and it was filtered. Thereafter, the residue was dried and separated by column chromatography to obtain 4.4 g of compound C-7 (yield: 49%).

[0112] 11H NMR (600 MHz, CDCl3) δ 9.13 - 9.11 (d, J = 12 Hz, 1H), 8.97 - 8.95 (d, J = 12 Hz, 1H), 8.75 - 8.73 (d, J = 12 Hz, 4H), 7.83 - 7.75 (m, 5H), 7.64 - 7.59 (m, 6H), 7.54 - 7.51 (m, 3H), 7.48 - 7.45 (t, J = 12 Hz, 3H), 7.40 - 7.39 (m, 2H)

[0113] Compound MW Tg M.P. C-7 522.6 105℃ 209℃

[0114] Example 5: Preparation of Compound C-302

[0115]

[0116] In a flask, 4.5 g of compound 5 (15.4 mmol), 5.4 g of 2-chloro-4-(naphthalen-2-yl)quinazoline (18.5 mmol), 0.09 g of DMAP (0.7 mmol), and 6.4 g of potassium carbonate (46.3 mmol) were dissolved in 77 mL of DMF, and the mixture was refluxed for 1.5 h. After completion of the reaction, the residue was filtered, dried, and separated by column chromatography to obtain 7.5 g of compound C-302 (yield: 80%).

[0117] 1 1H NMR (600 MHz, CDCl3) δ 9.03 - 9.02 (d, J = 6 Hz, 1H), 8.88 - 8.86 (d, J = 12 Hz, 1H), 8.39 (s, 1H), 8.22 - 8.21 (d, J = 6 Hz, 1H), 8.20 - 8.17 (d, J = 18 Hz, 1H), 8.15 - 8.05 (m, 2H), 8.00 - 7.98 (t, J = 6 Hz, 2H), 7.91 - 7.89 (m, 1H), 7.76 - 7.72 (m, 5H), 7.63 - 7.61 (m, 2H), 7.54 - 7.52 (m, 2H), 7.43 - 7.36 (m, 4H)

[0118] Compound MW Tg M.P. C-302 545.65 120.6℃ 257℃

[0119] Example 6: Preparation of Compound C-9

[0120]

[0121] In a flask, 5.0 g of compound 5 (17.16 mmol), 6.6 g of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (17.16 mmol), 0.6 g of tris(dibenzylideneacetone)dipalladium(0) (0.686 mmol), 0.7 g of SPhos (1.176 mmol) and 4.0 g of sodium tert-butoxide (42.9 mmol) were dissolved in 90 mL of o-xylene, and the mixture was refluxed for 4 h. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 6.2 g of compound C-9 (yield: 62%).

[0122] 1 H NMR (600 MHz, CDCl3, δ) 9.06 - 9.05 (d, J = 6.0 Hz, 2H), 8.85 - 8.83 (d, J = 12 Hz, 4H), 7.90 - 7.89 (m, 1H), 7.82 - 7.78 (m, 4H), 7.74 - 7.72 (m, 2H), 7.66 - 7.58 (m, 8H), 7.45 - 7.43 (m, 3H), 7.42 - 7.39 (m, 2H)

[0123] Compound MW Tg M.P. C-9 598.71 140.59℃ 260℃

[0124] Example 7: Preparation of Compound C-303

[0125]

[0126] In a flask, 4.3 g of compound 5 (14.83 mmol), 4.7 g of 6-chloro-2,4-diphenylquinazoline (14.83 mmol), 0.5 g of Pd2(dba)3 (0.593 mmol), 0.6 g of SPhos (1.483 mmol) and 3.6 g of sodium tert-butoxide (37.07 mmol) were dissolved in 80 mL of o-xylene, and the mixture was refluxed for 4 h. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 1.8 g of compound C-303 (yield: 21%).

[0127] 11H NMR (600 MHz, CDCl3, δ) 8.74 - 8.73 (d, J = 6.0 Hz, 2H), 8.37 - 8.36 (d, J = 6.0 Hz, 1H), 8.28 - 8.27 (d, J = 6.0 Hz, 1H), 8.05 - 8.04 (d, J = 6.0 Hz, 1H), 7.89 - 7.88 (d, J = 6.0 Hz, 2H), 7.85 - 7.83 (m, 1H), 7.75 - 7.73 (d, J = 12 Hz, 2H), 7.69 - 7.67 (m, 2H), 7.57 - 7.50 (m, 7H), 7.42 - 7.37 (m, 4H), 7.34 - 7.31 (m, 1H), 7.22 - 7.21 (m, 1H)

[0128] Compound MW Tg M.P. C-303 571.67 140.16℃ 189.3℃

[0129] Example 8: Preparation of Compound C-307

[0130]

[0131] In a flask, 5.4 g of compound 5 (18.53 mmol), 4.5 g of 2-chloro-3-naphthylquinoxaline (15.44 mmol), 2.1 g of potassium carbonate (15.44 mmol), and 0.9 g of DMAP (7.72 mmol) were dissolved in 80 mL of DMF, and the mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with MC, and the extracted organic layer was dried over magnesium sulfate. Thereafter, the residue was distilled under reduced pressure and separated by column chromatography to obtain 2.3 g of compound C-307 (yield: 47%).

[0132] 1 1H NMR (600 MHz, CDCl3, δ) 8.36 - 8.34 (d, J = 6.0 Hz, 1H), 8.23 (s, 1H), 8.17 - 8.16 (d, J = 6.0 HZ, 1H), 7.90 - 7.86 (m, 3H), 7.73 - 7.71 (d, J = 12 Hz, 1H), 7.68 - 7.63 (m, 4H), 7.50 - 7.48 (m, 2H), 7.40 - 7.35 (m, 6H), 7.32 - 7.24 (m, 2H)

[0133] Compound MW Tg M.P. C-307 545.65 133℃ 152℃

[0134] Example 9: Preparation of Compound C-13

[0135]

[0136] In a flask, 4.0 g of compound 5 (13.73 mmol), 4.0 g of 2-chloro-3-phenylquinoxaline (16.47 mmol), 3.8 g of potassium carbonate (27.46 mmol), and 0.84 g of DMAP (6.87 mmol) were dissolved in 68 mL of DMF, and the mixture was refluxed for 18 h. After the reaction was completed, the reaction mixture was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with MC, and the extracted organic layer was dried over magnesium sulfate. Thereafter, the residue was distilled under reduced pressure and separated by column chromatography to obtain 2.3 g of compound C-13 (yield: 33.8%).

[0137] 1 H NMR (600 MHz, CDCl3, δ) 8.32 - 8.30 (m, 1H), 8.16 - 8.15 (m, 1H), 7.89 - 7.83 (m, 3H), 7.73 (d, J = 7.38 Hz, 1H), 7.69 - 7.68 (m, 2H), 7.60 - 7.54 (m, 2H), 7.50 (d, J = 9.00 Hz, 1H), 7.42 - 7.37 (m, 3H), 7.29 - 7.27 (m, 3H), 7.21 - 7.15 (m, 4H)

[0138] Compound MW Tg M.P. C-13 495.59 124.88℃ 154℃-164℃

[0139] Example 10: Preparation of Compound C-304

[0140]

[0141] Synthesis of Compound 10-1

[0142] 9 g of compound 5 (30.89 mmol), 10.6 g of 1-bromo-3-iodobenzene (61.78 mmol), 3 g of CuI (15.44 mmol), 1.8 g of EDA (30.89 mmol), and 16.4 g of K3PO4 (77.22 mmol) were added to 155 mL of toluene, and the mixture was stirred under reflux for 1 day. After the reaction was completed, the reaction mixture was cooled to room temperature, and then the resulting solid was filtered under reduced pressure. The solid was dissolved in CHCl3, and the mixture was separated by column chromatography with MC / Hex to obtain 10 g of compound 10-1 (yield: 75%).

[0143] Synthesis of Compound C-304

[0144] 5.7 g of Compound 10-1 (12.77 mmol), 2.98 g of 4-dibenzofuranboronic acid (14.05 mmol), 0.73 g of Pd(PPh3)4 (0.638 mmol), and 3.5 g of K2CO3 (25.54 mmol) were added to 50 mL of toluene, 13 mL of EtOH, and 13 mL of purified water, and the mixture was stirred under reflux for 2 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then the resulting solid was filtered under reduced pressure. The solid was dissolved in CHCl3, and the mixture was separated by column chromatography using MC / Hex to obtain 2.9 g of Compound C-304 (yield: 43%).

[0145] 1 H NMR (600 MHz, DMSO-d6, δ) 8.232 - 8.206 (m, 3H), 8.111 - 8.098 (d, 1H), 7.962 - 7.946 (m, 1H), 7.929 - 7.903 (m, 3H), 7.896 - 7.882 (d, 1H), 7.806 - 7.802 (d, 2H), 7.783 - 7.759 (t, 2H), 7.738 - 7.723 (d, 1H), 7.635 - 7.620 (m, 1H), 7.581 - 7.548 (m, 2H), 7.513 - 7.440 (m, 6H)

[0146] Compound MW Tg M.P. C-304 533.6 119℃ 208℃

[0147] Example 11: Preparation of Compound C-306

[0148]

[0149] In a flask, 5.0 g of Compound 10-1 (11.2 mmol), 3.0 g of N-phenyl-[1,1'-biphenyl]-4-amine (12.3 mmol), 0.51 g of Pd2(dba)3 (0.56 mmol), 0.46 g of SPhos (1.12 mmol), and 2.7 g of sodium tert-butoxide (28 mmol) were added to 60 mL of toluene, and the mixture was refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 2.3 g of Compound C-306 (yield: 34%).

[0150] 11H NMR (600 MHz, DMSO-d6, δ) 7.896 - 7.880 (m, 1H), 7.863 - 7.850 (d, 1H), 7.805 - 7.790 (d, 1H), 7.758 - 7.745 (d, 1H), 7.733 - 7.720 (d, 1H), 7.669 - 7.650 (m, 2H), 7.640 - 7.627 (d, 1H), 7.604 - 7.566 (m, 2H), 7.522 - 7.507 (d, 1H), 7.447 - 7.384 (m, 7H), 7.373 - 7.347 (t, 1H), 7.335 - 7.311 (t, 1H), 7.269 - 7.237 (m, 6H), 7.175 - 7.156 (d, 1H), 7.147 - 7.122 (t, 1H), 7.069 - 7.062 (t, 1H)

[0151] Compound MW Tg M.P. C-306 610.8 114℃ 132℃

[0152] Example 12: Preparation of Compound C-333

[0153]

[0154] In a flask, 2.6 g of compound 12 (7.6 mmol), 2.95 g of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (7.6 mmol), 0.27 g of tris(dibenzylideneacetone)dipalladium(0) (0.3 mmol), 0.3 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.7 mmol) and 1.8 g of sodium tert-butoxide (19 mmol) were dissolved in 50 mL of o-xylene, and the mixture was refluxed for 12 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 1.9 g of compound C-333 (yield: 38%).

[0155] 11H NMR (600 MHz, DMSO-d6, δ) 9.086 - 9.072 (d, 1H), 8.887 - 8.882 (t, 1H), 8.821 - 8.807 (d, 1H), 8.714 - 8.699 (d, 4H), 8.676 - 8.663 (d, 1H), 8.014 - 7.988 (t, 1H), 7.883 - 7.833 (m, 3H), 7.781 - 7.768 (d, 1H), 7.691 - 7.665 (t, 2H), 7.640 - 7.575 (m, 6H), 7.540 - 7.485 (m, 3H), 7.399 - 7.343 (m, 3H), 6.982 - 6.968 (d, 1H)

[0156] Compound MW M.P. Tg C-333 648.77 195℃ 165℃

[0157] Example 13: Preparation of Compound C-372

[0158]

[0159] Synthesis of Compound 13-1

[0160] In a flask, 70 g of Compound 5 (240 mmol) and 40.6 g of N-bromosuccinimide (NBS) (255 mmol) were dissolved in 1200 mL of dimethylformamide, and the mixture was stirred at 0 °C for 3 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 68 g of Compound 13-1 (yield: 76%).

[0161] Synthesis of Compound 13-2

[0162] In a flask, 47.3 g of Compound 13-1 (127 mmol), 42 g of bis(pinacolato)diboron (166 mmol), 4.5 g of dichlorobis(triphenylphosphine)palladium(II) (PdCl2(PPh3)2) (6.4 mmol), and 25 g of potassium acetate (255 mmol) were dissolved in 635 mL of 1,4-dioxane, and the mixture was refluxed for 4 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 31.5 g of Compound 13-2 (yield: 59%).

[0163] Synthesis of Compound 13-3

[0164] In a flask, 4.5 g of Compound 13-2 (10.7 mmol), 1.9 g of 1-bromobenzene (11.85 mmol), 0.63 g of tetrakis(triphenylphosphine)palladium(0) (0.54 mmol), and 3.7 g of potassium carbonate (26.95 mmol) were dissolved in 54 mL of toluene, 13 mL of ethanol, and 13 mL of water, and the mixture was refluxed for 12 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual water was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 2.2 g of Compound 13-3 (yield: 56%).

[0165] Synthesis of Compound C-372

[0166] In a flask, 2.2 g of Compound 13-3 (5.9 mmol), 1.58 g of 2-chloro-3-phenylquinoxaline (6.57 mmol), 3.89 g of cesium carbonate (11.96 mmol), and 0.36 g of 4-dimethylaminopyridine (2.99 mmol) were dissolved in 30 mL of dimethyl sulfoxide (DMSO), and the mixture was stirred at 100 °C for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with ethyl acetate, and the residual water was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 2.9 g of Compound C-372 (yield: 85%).

[0167] Compound MW M.P. Tg C-372 571.68 210℃ 167℃

[0168] Example 14: Preparation of Compound C-334

[0169]

[0170] Synthesis of Compound 14-1

[0171] In a flask, 27 g of Compound 13-2 (64.7 mmol), 14.4 g of 1-bromo-2-nitrobenzene (71.2 mmol), 3.7 g of tetrakis(triphenylphosphine)palladium(0) (3.2 mmol), and 22.4 g of potassium carbonate (162 mmol) were dissolved in 320 mL of toluene, 80 mL of ethanol, and 80 mL of water, and the mixture was refluxed for 12 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate, and the residual water was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 26.7 g of Compound 14-1 (yield: 100%).

[0172] Synthesis of Compound 14-2

[0173] In a flask, 26.7 g of Compound 14-1 (64.7 mmol), 18.5 g of copper(I) iodide (97 mmol), and 27.4 g of tripotassium phosphate (129 mmol) were dissolved in 18 mL of 1-iodobenzene (162 mmol), 13 mL of ethylenediamine (EDA) (194 mmol), and 325 mL of toluene, and the mixture was refluxed for 2 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 15.7 g of Compound 14-2 (yield: 49%).

[0174] Synthesis of Compound 14-3

[0175] In a flask, 13.1 g of Compound 14-2 (26.8 mmol) was added to 180 mL of triethyl phosphite and 180 mL of 1,2-dichlorobenzene, and the mixture was stirred at 200 °C for 2 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the reaction mixture was cooled to room temperature and then hexane was added to obtain a solid. After the solvent was removed from the resulting solid by filtration, the residue was separated by column chromatography to obtain 0.71 g of Compound 14-3 (yield: 5.8%).

[0176] Synthesis of Compound C-334

[0177] In a flask, 0.71 g of Compound 14-3 (1.56 mmol), 0.45 g of 2-chloro-3-phenylquinoxaline (1.87 mmol), 1.01 g of cesium carbonate (3.12 mmol), and 0.095 g of 4-dimethylaminopyridine (0.78 mmol) were dissolved in 30 mL of dimethyl sulfoxide, and the mixture was stirred at 100 °C for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and distilled water and methanol were added thereto. After the solvent was removed from the resulting solid by filtration, the residue was separated by column chromatography to obtain 0.50 g of Compound C-334 (yield: 49%).

[0178] 11H NMR (600 MHz, CDCl3, δ) 8.333 - 8.248 (m, 3H), 8.192 - 8.099 (m, 1H), 7.911 - 7.820 (m, 3H), 7.767 - 7.754 (d, 1H), 7.613 - 7.526 (m, 5H), 7.488 - 7.410 (m, 4H), 7.395 - 7.347 (m, 3H), 7.329 - 7.296 (m, 2H), 7.230 - 7.205 (m, 2H), 7.179 - 7.153 (m, 1H), 7.130 - 7.075 (m, 1H), 7.056 - 7.030 (m, 1H), 6.874 - 6.688 (m, 1H)

[0179] Compound MW M.P. C-334 660.78 290℃

[0180] Example 15: Preparation of Compound C-197

[0181]

[0182] Synthesis of Compound 15-1

[0183] In a flask, 40 g of compound 13 - 1 (108 mmol), 25.4 g of (2 - methylthio)phenylboronic acid (153.5 mmol), 6.26 g of tetrakis(triphenylphosphine)palladium(0) (5.40 mmol), and 26.3 g of potassium carbonate (272.0 mmol) were dissolved in 536 mL of tetrahydrofuran and 134 mL of distilled water, and the mixture was refluxed at 100 °C for 18 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 40 g of compound 15 - 1 (89%).

[0184] Synthesis of Compound 15-2

[0185] In a flask, 40 g of compound 15 - 1 (96.8 mmol) was dissolved in 400 mL of tetrahydrofuran, 200 mL of acetic acid, and 12.6 mL of 34.5% hydrogen peroxide (145.2 mmol), and the mixture was stirred at room temperature for 20 hours. After completion of the reaction, the mixture was concentrated, and the organic layer was extracted with dichloromethane and aqueous sodium bicarbonate, and then the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried to obtain 42 g of compound 15 - 2 (yield: 100%).

[0186] Synthesis of Compound 15-3

[0187] In a flask, 42 g of Compound 15-2 (96.4 mmol) was dissolved in 190 mL of trifluoromethanesulfonic acid, and the mixture was stirred at room temperature for 3 days. After the reaction was completed, 50 mL of pyridine and 1 M aqueous NaOH were added to the mixture at 0 °C to adjust the pH to 7 to 8, and the mixture was refluxed at 100 °C for 1 hour. After removing the solvent by filtration, the resulting solid was separated by column chromatography to obtain 9.1 g of Compound 15-3 (yield: 24%).

[0188] Synthesis of Compound C-197

[0189] In a flask, 4 g of Compound 15-3 (10.1 mmol), 3 g of 2-chloro-3-phenylquinoxaline (12.1 mmol), 6.6 g of cesium carbonate (20.2 mmol), and 0.62 g of 4-dimethylaminopyridine (5.1 mmol) were dissolved in 50 mL of dimethyl sulfoxide, and the mixture was stirred at 100 °C for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and distilled water and methanol were added thereto. After removing the solvent from the resulting solid by filtration, the residue was separated by column chromatography to obtain 4.8 g of Compound C-197 (yield: 79%).

[0190] 1 H NMR (600 MHz, CDCl3, δ) 8.337 - 8.310 (m, 1H), 8.247 - 8.202 (m, 1H), 8.196 - 8.151 (m, 1H), 7.957 - 7.945 (m, 1H), 7.928 (s, 1H), 7.912 - 7.837 (m, 3H), 7.794 - 7.728 (m, 3H), 7.685 - 7.672 (d, 1H), 7.531 - 7.498 (m, 1H), 7.469 - 7.414 (m, 2H), 7.348 - 7.300 (m, 2H), 7.262 - 7.173 (m, 4H), 7.102 - 7.087 (d, 1H), 7.036 - 6.955 (m, 1H)

[0191] Compound MW M.P. Tg C-197 601.73 317℃ 194℃

[0192] Example 16: Preparation of Compound C-339

[0193]

[0194] Synthesis of Compound 16-1

[0195] 15.6 g of Compound 5 (53.5 mmol), 20 g of 2,3-dichlorobenzo[f]quinoxaline (80.3 mmol), 15 g of potassium carbonate (107.0 mmol) and 3.3 g of DMAP (26.7 mmol) were added to 270 mL of N,N-dimethylformamide, and the mixture was stirred at 150 °C for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 2.2 g of Compound 16-1 (yield: 8%).

[0196] Synthesis of Compound C-339

[0197] In a reaction vessel, 2.2 g of Compound 16-1 (4.4 mmol), 800 mg of phenylboronic acid (6.6 mmol), 250 mg of tetrakis(triphenylphosphine)palladium(0) (0.2 mmol) and 1.2 g of sodium carbonate (10.9 mmol) were added to 20 mL of toluene, 5.5 mL of distilled water and 5 mL of ethanol, and the mixture was refluxed at 130 °C for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 1.8 g of Compound C-339 (yield: 76%).

[0198] 1 H NMR (600 MHz, CDCl3, δ) 9.403 - 9.390 (d, 1H), 8.119 - 8.105 (d, 1H), 8.012 - 7.997 (d, 1H), 7.994 - 7.979 (d, 1H), 7.867 - 7.851 (m, 1H), 7.847 - 7.822 (td, 1H), 7.815 - 7.788 (td, 1H), 7.734 - 7.722 (d, 1H), 7.686 - 7.656 (m, 4H), 7.600 - 7.585 (m, 1H), 7.509 - 7.494 (d, 1H), 7.404 - 7.389 (m, 2H), 7.385 - 7.359 (t, 1H), 7.295 - 7.264 (m, 2H), 7.250 - 7.219 (t, 1H), 7.208 - 7.182 (m, 3H).

[0199] Compound MW M.P. Tg C-339 545.65 247℃ 148℃

[0200] Example 17: Preparation of Compound C-338

[0201]

[0202] Synthesis of Compound 17-1

[0203] 15.6g of compound 5 (53.5mmol), 20g of 2,3-dichlorobenzo [f] quinoxaline (80.3mmol), 15g of potassium carbonate (107.0mmol) and 3.3g of DMAP (26.7mmol) were added to 270mL of N, N-dimethylformamide, and the mixture was stirred at 150 ° C for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and the solvent was removed by rotary evaporation. The residue was separated by column chromatography to obtain 2.8g of compound 17-1 (yield: 10%).

[0204] Synthesis of Compound C-338

[0205] In a reaction vessel, 2.7 g of compound 17-1 (5.4 mmol), 1 g of phenylboronic acid (8.0 mmol), 310 mg of tetrakis(triphenylphosphine)palladium (0) (0.3 mmol) and 1.4 g of sodium carbonate (13.4 mmol) were added to 28 mL of toluene, 6.7 mL of distilled water and 7 mL of ethanol, and the mixture was stirred at 130 ° C for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and the solvent was removed by a rotary evaporator. The residue was separated by column chromatography to obtain 2.5 g of compound C-338 (yield: 86%).

[0206] 1 H NMR(600MHz, CDCl3, δ)9.119-9.106(d,1H),8.160-8.125(dd,2H),8.001-7.988(d,1H),7.878-7.862(m,1H),7.782-7.755(td,1H),7.748-7 .726(m,2H),7.709-7.685(t,2H),7.623-7.594(m,3H),7.518-7.503( d,1H),7.418-7.371(m,4H),7.305-7.271(m,2H),7.200-7.182(m,3H).

[0207] Compound MW M.P. Tg C-338 545.65 299℃ 149℃

[0208] Example 18: Preparation of Compound C-379

[0209]

[0210] In a flask, 4.0 g of compound 5 (13.73 mmol), 5.2 g of 5-chloro-2,3-diphenylquinoxaline (16.47 mmol), 0.629 g of tris(dibenzylideneacetone)dipalladium(0) (0.686 mmol), 0.564 mg of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.0 mmol) and 3.9 g of sodium tert-butoxide (41 mmol) were dissolved in 80 mL of 1,2-dimethylbenzene, and the mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with MC, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was distilled under reduced pressure and separated by column chromatography to obtain 2.8 g of compound C-379 (yield: 35.67%).

[0211] 1 H NMR (600 MHz, CDCl3, δ) 8.323 - 8.307 (d, J = 7.2 Hz, 1H), 7.947 - 7.935 (m, 2H), 7.883 - 7.867 (m, 1H), 7.762 - 7.749 (d, J = 7.2 Hz, 2H), 7.686 - 7.673 (d, J = 7.8 Hz, 1H), 7.633 - 7.603 (m, 2H), 7.568 - 7.556 (d, J = 7.2 Hz, 2H), 7.404 - 7.337 (m, 6H), 7.307 - 7.281 (t, J = 7.8 Hz, 1H), 7.195 - 7.281 (m, 3H), 7.144 - 7.110 (t, J = 7.2 HZ, 1H), 7.087 - 7.074 (d, J = 7.8 HZ, 1H), 7.010 - 6.990 (m, 2H)

[0212] Compound MW Tg M.P. C-379 571.67 135.60℃ 142℃

[0213] Example 19: Preparation of Compound C-389

[0214]

[0215] In a flask, 6.0 g of compound 5 (21 mmol), 7.8 g of 2-([1,1'-biphenyl]-3-yl)-3-chloroquinoxaline (25 mmol), 8.5 g of potassium carbonate (62 mmol) and 0.126 g of 4-dimethylaminopyridine (1 mmol) were dissolved in 100 mL of dimethylformamide, and the mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with MC and dried with magnesium sulfate. Thereafter, the residue was distilled under reduced pressure and separated by column chromatography to obtain 8.8 g of compound C-389 (yield: 74%).

[0216] 1 1H NMR (600 MHz, CDCl3, δ) 8.338 - 8.325 (d, J = 7.8 Hz, 1H), 8.228 - 8.212 (d, J = 8.7 Hz, 1H), 7.907 - 7.877 (m, 3H), 7.783 - 7.758 (m, 2H), 7.686 - 7.683 (d, J = 7.8 Hz, 2H), 7.630 - 7.590 (m, 1H), 7.523 - 7.508 (d, J = 9 Hz, 2H), 7.447 - 7.390 (m, 3H), 7.341 - 7.332 (m, 2H), 7.284 - 7.236 (m, 3H), 7.205 (s, 1H), 7.088 - 7.066 (m, 1H), 7.016 - 7.002 (d, J = 7.8 Hz, 2H), 6.903 - 6.877 (m, 2H)

[0217] Compound MW Tg M.P. C-389 571.67 120.06℃ 202℃

[0218] Example 20: Preparation of Compound C-395

[0219]

[0220] In a flask, 7.9 g of compound 5 (27 mmol), 7.9 g of 2-chloro-3-(phenyl-D5) quinoxaline (33 mmol), 11.24 g of potassium carbonate (81 mmol) and 0.166 g of 4-dimethylaminopyridine (1 mmol) were dissolved in 135 mL of dimethylformamide, and the mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and distilled water was added thereto. The organic layer was extracted with MC and dried over magnesium sulfate. Thereafter, the residue was distilled under reduced pressure and separated by column chromatography to obtain 3.2 g of compound C-395 (yield: 23.7%).

[0221] 1 1H NMR (600 MHz, CDCl3, δ) 8.318 - 8.305 (d, J = 7.8 Hz, 1H), 8.164 - 8.151 (d, J = 7.8 Hz, 1H), 7.892 - 7.834 (m, 3H), 7.740 - 7.728 (d, J = 7.2 Hz, 1H), 7.691 - 7.679 (d, J = 7.2 Hz, 2H), 7.603 - 7.587 (m, 1H), 7.508 - 7.493 (d, J = 9 Hz, 1H), 7.413 - 7.370 (m, 3H), 7.291 - 7.250 (m, 2H), 7.212 - 7.197 (d, J = 9 Hz, 1H)

[0222] Compound MW Tg M.P. C-395 500.62 127℃ 158℃

[0223] Example 21: Preparation of Compound C-380

[0224]

[0225] In a flask, 10 g of compound 5 (28.82 mmol), 7.0 g of 2-chloro-3-(4-(naphthalen-2-yl)phenyl)quinoxaline (24.02 mmol), 1.5 g of 4-dimethylaminopyridine (12.01 mmol) and 3.3 g of potassium carbonate (24.02 mmol) were dissolved in 130 mL of dimethylformamide, and the mixture was refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 8.8 g of compound C-380 (yield: 59%).

[0226] 1 H NMR (600 MHz, CDCl3, δ) 8.33 - 8.32 (d, J = 6.0 Hz, 1H), 8.16 - 8.15 (d, J = 6.0 Hz, 1H), 7.88 - 7.84 (m, 4H), 7.80 - 7.77 (m, 3H), 7.74 - 7.73 (d, J = 6.0 Hz, 1H), 7.69 - 7.66 (m, 4H), 7.57 - 7.56 (m, 2H), 7.53 - 7.50 (m, 3H), 7.43 - 7.37 (m, 5H), 7.32 - 7.23 (m, 3H)

[0227] Compound MW Tg M.P. C-380 621.74 145.6℃ 262.7℃

[0228] Example 22: Preparation of Compound C-394

[0229]

[0230] In a flask, 6 g of compound 5 (20.59 mmol), 9.1 g of 2-(3-chloroquinoxalin-2-yl)-9-phenyl-9H-carbazole (22.65 mmol), 1.2 g of 4-dimethylaminopyridine (10.29 mmol) and 2.8 g of potassium carbonate (20.59 mmol) were dissolved in 100 mL of dimethylformamide, and the mixture was refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 9.6 g of compound C-394 (yield: 70%).

[0231] 11H NMR (600 MHz, CDCl3, δ) 8.31 - 8.30 (d, J = 6.0 Hz, 1H), 8.13 - 8.11 (d, J = 12.0 Hz, 1H), 8.04 - 8.03 (d, J = 6.0 Hz, 1H), 7.94 - 7.93 (d, J = 6.0 Hz, 1H), 7.86 - 7.81 (m, 3H), 7.74 - 7.73 (d, J = 6.0 Hz, 1H), 7.65 - 7.63 (d, J = 12.0 Hz, 2H), 7.61 - 7.60 (m, 1H), 7.44 - 7.36 (m, 4H), 7.30 - 7.28 (m, 1H), 7.23 - 7.15 (m, 6H), 6.98 - 6.93 (m, 3H), 6.88 - 6.87 (m, 2H).

[0232] Compound MW Tg M.P. C-394 660.78 154.09℃ 290.5℃

[0233] Example 23: Preparation of Compound C-346

[0234]

[0235] In a flask, 6.0 g of compound 5 (20.59 mmol), 9.1 g of 2-(2-chloroquinazolin-4-yl)-9-phenyl-9H-carbazole (22.65 mmol), 1.2 g of 4-dimethylaminopyridine (10.29 mmol), and 2.8 g of potassium carbonate (20.59 mmol) were dissolved in 100 mL of dimethylformamide, and the mixture was refluxed for 3 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 10 g of compound C-346 (yield: 77%).

[0236] 1 1H NMR (600 MHz, CDCl3, δ) 9.01 - 9.00 (d, J = 6.0 Hz, 1H), 8.85 - 8.84 (d, J = 6.0 Hz, 1H), 8.34 - 8.33 (d, J = 6.0 Hz, 1H), 8.23 - 8.22 (d, J = 6.0 Hz, 2H), 8.11 - 8.10 (d, J = 6.0 Hz, 1H), 8.05 (s, 1H), 7.86 - 7.82 (m, 2H), 7.79 - 7.77 (m, 1H), 7.75 - 7.71 (m, 3H), 7.67 - 7.64 (m.3H), 7.59 - 7.57 (m, 2H), 7.53 - 7.52 (m, 1H), 7.50 - 7.47 (m, 3H), 7.43 - 7.37 (m, 2H), 7.36 - 7.35 (m, 4H)

[0237] Compound MW Tg M.P. C-346 660.78 158℃ 189.9℃

[0238] Example 24: Preparation of Compound C-388

[0239]

[0240] In a flask, 12g of compound 5 (41.1mmol), 14.8g of 2-(4-bromophenyl)-4-phenylquinazoline (41.1mmol), 1.5g of tris(dibenzylideneacetone)dipalladium (0) (1.6mmol), 1.7g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (4.1mmol) and 9.8g of sodium tert-butoxide (102.9mmol) were dissolved in 274mL of o-xylene, and the mixture was refluxed for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and separated by column chromatography to obtain 1.1g of compound C-388 (yield: 4.7%).

[0241] 1 H NMR(600MHz, CDCl3, δ)8.927-8.912(d,J=7.8Hz,2H),8.199-8.160(m,2H),7.925-7.910(m,3H),7.865-7.855(m,1H ),7.759-7.672(m,6H),7.620-7.587(m,5H),7.540-7.525(d,J=9Hz,1H),7.401-7.375(m,3H),7.339-7.328(m,2H).

[0242] Compound MW Tg M.P. C-388 571.6 133℃ 241℃

[0243] Example 25: Preparation of Compound C-381

[0244]

[0245] In a flask, 5.7g of compound 5 (19.5mmol), 7.7g of 2-chloro-3-(dibenzo[b,d]furan-1-yl)quinoxaline (23.2mmol), 0.1g of 4-dimethylaminopyridine (0.9mmol) and 8.1g of potassium carbonate (58.5mmol) were dissolved in 99mL of dimethylformamide and the mixture was refluxed for 3.5 hours. After the reaction was complete, the reaction mixture was cooled, and methanol and water were added thereto and filtered. Thereafter, the residue was dried and separated by column chromatography to obtain 6g of compound C-381 (yield: 52%).

[0246] 11H NMR (600 MHz, CDCl3, δ) 8.324 - 8.271 (m, 2H), 7.962 - 7.942 (m, 2H), 7.867 - 7.855 (d, J = 7.2 Hz, 1H), 7.821 - 7.805 (m, 1H), 7.705 - 7.693 (d, J = 7.2 Hz, 1H), 7.655 - 7.595 (m, 3H), 7.567 - 7.537 (m, 2H), 7.394 - 7.272 (m, 8H), 7.124 - 7.155 (m, 1H), 6.984 - 6.958 (t, J = 7.2 Hz, 1H), 6.830 - 6.817 (d, J = 7.8 Hz, 1H)

[0247] Compound MW Tg M.P. C-381 585.6 154.79℃ 233℃

[0248] Example 26: Preparation of Compound C-378

[0249]

[0250] In a flask, 3.8 g of compound 5 (13 mmol), 5.0 g of 2-([1,1'-biphenyl]-4-yl)-3-chloroquinoxaline (16 mmol), 800 mg of DMAP (7 mmol) and 3.6 g of potassium carbonate (26 mmol) were dissolved in 55 mL of dimethylformamide, and the mixture was refluxed for 18 hours. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 1.4 g of compound C-378 (yield: 19%).

[0251] 1 1H NMR (600 MHz, CDCl3, δ) 8.33 - 8.32 (m, 1H), 8.17 - 8.16 (m, 1H), 7.90 - 7.84 (m, 3H), 7.74 (d, J = 7.50 Hz, 1H), 7.69 (t, J = 6.72 Hz, 2H), 7.63 (d, J = 8.4 Hz, 2H), 7.61 - 7.59 (m, 1H), 7.51 (d, J = 9.00 Hz, 1H), 7.45 - 7.37 (m, 7H), 7.35 - 7.27 (m, 5H), 7.23 (d, J = 8.79 Hz, 1H)

[0252] Compound MW Tg M.P. C-378 571.68 137.6℃ 189℃

[0253] Example 27: Preparation of Compound C-386

[0254]

[0255] In a flask, 5.1 g of compound 5 (17 mmol), 5.0 g of 6-chloro-2,3-diphenylquinoxaline (16 mmol), 578 mg of tris(dibenzylideneacetone)dipalladium(0) (0.631 mmol), 648 mg of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (2 mmol) and 3.8 g of sodium tert-butoxide (39 mmol) were dissolved in 100 mL of toluene, and the mixture was refluxed for 16 h. After the reaction was completed, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 7.6 g of compound C-386 (yield: 84%).

[0256] 1 H NMR (600 MHz, CDCl3, δ) 8.01 (s, 1H), 8.40 (d, J = 5.4 Hz, 1H), 7.99 (dd, J = 5.4 Hz; 2.22 Hz, 1H), 7.89 - 7.87 (m, 1H), 7.79 - 7.77 (m, 2H), 7.74 - 7.70 (m, 2H), 7.63 - 7.60 (m, 2H), 7.59 - 7.56 (m, 4H), 7.44 - 7.34 (m, 11H)

[0257] Compound MW Tg M.P. C-386 571.68 138.80℃ 295℃

[0258] Example 28: Preparation of Compound C-387

[0259]

[0260] 6.6 g of compound 10-1 (14.78 mmol), 3.4 g of dibenzo[b,d]furan-1-ylboronic acid (16.24 mmol), 0.85 g of tetrakis(triphenylphosphine)palladium(0) (0.739 mmol) and 4 g of potassium carbonate (29.57 mmol) were added to 60 mL of toluene, 15 mL of ethanol and 15 mL of purified water, and the mixture was stirred under reflux for 1 day. After the reaction was completed, the reaction mixture was cooled to room temperature, and then the resulting solid was filtered under reduced pressure. The solid was dissolved in CHCl3, and the mixture was separated by column chromatography with MC / Hex to obtain 3.5 g of compound C-387 (yield: 45%).

[0261] 11H NMR (600 MHz, DMSO, δ) 7.953 - 7.927 (m, 2H), 7.896 - 7.872 (t, 2H), 7.848 - 7.810 (m, 3H), 7.793 - 7.746 (m, 4H), 7.656 - 7.601 (m, 4H), 7.539 - 7.511 (t, 1H), 7.485 - 7.443 (m, 4H), 7.419 - 7.393 (t, 1H), 7.369 - 7.356 (d, 1H), 7.294 - 7.269 (t, 1H)

[0262] Compound MW M.P. Tg C-387 533.6 224℃ 117℃

[0263] Example 29: Preparation of Compound C-393

[0264]

[0265] In a flask, 4.4 g of compound 5 (15.16 mmol), 5.0 g of 9-chloro-6-phenyl-6H-indolo[2,3-b]quinoxaline (15.16 mmol), 0.5 g of tris(dibenzylideneacetone)dipalladium(0) (0.606 mmol), 0.6 g of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (1.516 mmol) and 12 g of sodium tert-butoxide (37.90 mmol) were added to 100 mL of o-xylene, and the mixture was refluxed for 4 hours. After completion of the reaction, the organic layer was extracted with ethyl acetate after distillation under reduced pressure, and the residual moisture was removed by using magnesium sulfate. Thereafter, the residue was dried and separated by column chromatography to obtain 1.9 g of compound C-393 (yield: 21%).

[0266] 1 1H NMR (600 MHz, CDCl3, δ) 8.74 (s, 1H), 8.33 - 8.32 (d, J = 6.0 Hz, 1H), 8.15 - 8.14 (d, J = 6.0 Hz, 1H), 7.91 - 7.90 (m, 1H), 7.84 - 8.73 (m, 2H), 7.80 - 7.78 (m, 5H), 7.77 - 7.69 (m, 5H), 7.64 - 7.63 (m.1H), 7.60 - 7.59 (m, 1H), 7.50 - 7.49 (d, J = 6.0 Hz, 1H), 7.43 - 7.41 (m, 3H), 7.36 - 7.34 (t, J = 6.0 Hz, 1H), 7.28 - 7.27 (m, 1H)

[0267] Compound MW Tg MP C-393 584.67 129.07℃ 294℃

[0268] Example 30: Preparation of Compound C-447

[0269]

[0270] Synthesis of compound 30-1

[0271] In a flask, add 8.0g of compound 13-1 (21.6mmol), 12.1g of 4-iodobiphenyl (43.2mmol), 1.0g of tris (dibenzylideneacetone) dipalladium (0) (1.08mmol), 0.87mL of tri-tert-butylphosphine (2.16mmol, 50% toluene solution), 5.2g of sodium tert-butoxide (54.0mmol) and 216mL of toluene, and reflux the mixture for 18 hours. After the reaction is complete, the reaction mixture is cooled to room temperature, and the solvent is removed by rotary evaporator. Residue is separated by column chromatography to obtain 7.5g of compound 30-1 (yield: 66%).

[0272] Synthesis of compound 30-2

[0273] In a flask, 7.5g of compound 30-1 (14.4mmol), 4.5g of 2-(4,4,5,5-tetramethyl-1,3,2-dioxyborene-2-yl) methyl benzoate (17.3mmol), 323mg of palladium acetate (Pd(OAc)2) (1.44mmol), 1.2g of ligand (2-dicyclohexylphosphonium-2', 6'-dimethoxybiphenyl) (2.88mmol) and 14g of cesium carbonate (43.2mmol) were added to 80mL of xylene, 40mL of ethanol and 40mL of distilled water, and the mixture was stirred under reflux for 18 hours. The reaction mixture was cooled to room temperature and distilled water was added thereto. The organic layer was extracted with MC and dried over magnesium sulfate. Thereafter, the residue was distilled under reduced pressure and separated by column chromatography to obtain 2.2g of compound 30-2 (yield: 27%).

[0274] Synthesis of compound 30-3

[0275] In a flask, 2.2 g of compound 30-2 (3.8 mmol), 2 mL of Eaton's reagent and 13 mL of benzene chloride were added, and the mixture was stirred under reflux for 18 hours. The reaction mixture was cooled to room temperature and an aqueous sodium bicarbonate solution was added thereto. The organic layer was extracted with ethyl acetate (EA) and dried over magnesium sulfate. Thereafter, the residue was distilled under reduced pressure and separated by column chromatography to obtain 1.5 g of compound 30-3 (yield: 71%).

[0276] Synthesis of compound C-447

[0277] In a flask, 244 mg of iodine (0.96 mmol), 0.48 mL of hypophosphorous acid (4.4 mmol, 50% aqueous solution), and 14 mL of acetic acid were added, and the mixture was stirred at 80 °C for 30 minutes. 1.5 g of Compound 30-3 (2.75 mmol) was slowly added dropwise to the reaction mixture and stirred under reflux for 4 hours. The reaction solution was cooled to room temperature, and the precipitated solid was filtered and washed with a large amount of water and ethanol. After removing the solvent from the obtained solid through the filter, the residue was separated by column chromatography to obtain 270 mg of Compound C-447 (yield: 18%).

[0278] 1 H NMR (600 MHz, CDCl3, δ) 8.051 - 8.036 (dd, 1H), 7.967 - 7.953 (m, 1H), 7.920 - 7.909 (d, 1H), 7.857 - 7.843 (d, 2H), 7.797 - 7.784 (d, 1H), 7.720 - 7.698 (m, 2H), 7.669 - 7.643 (m, 3H), 7.562 - 7.500 (m, 5H), 7.463 - 7.416 (m, 5H), 7.217 - 7.190 (m, 2H), 4.153 - 4.188 (d, 1H), 3.949 - 3.913 (d, 1H).

[0279] Figure 1 The structure of an organic electroluminescent device according to an embodiment of the present disclosure is schematically shown. Hereinafter, reference will be made to Figure 1 Describe an organic electroluminescent device according to an embodiment of the present disclosure.

[0280] Reference Figure 1, the organic electroluminescent device of the present disclosure includes a substrate, an anode formed on the substrate, a first unit formed on the anode, a charge generation layer formed on the first unit, a second unit formed on the charge generation layer, and a cathode formed on the second unit. The first unit may include one or more light-emitting layers and may contain the compound represented by Formula 1 of the present disclosure. The first unit may include a first hole injection layer formed on the anode, a first hole transport layer formed on the first hole injection layer, a first light-emitting layer formed on the first hole transport layer, a first electron transport layer formed on the first light-emitting layer, and a first electron injection layer formed on the first electron transport layer. The first hole injection layer, the first hole transport layer, the first light-emitting layer, the first electron transport layer, and the first electron injection layer may each be a single layer or multiple layers. Additionally, the second unit may include one or more light-emitting layers and may contain the compound represented by Formula 1 of the present disclosure. The second unit may include a second hole injection layer formed on the charge generation layer, a second hole transport layer formed on the second hole injection layer, a second light-emitting layer formed on the second hole transport layer, a second electron transport layer formed on the second light-emitting layer, and a second electron injection layer formed on the second electron transport layer. The second hole injection layer, the second hole transport layer, the second light-emitting layer, the second electron transport layer, and the second electron injection layer may each be a single layer or multiple layers. Furthermore, the organic electroluminescent device of the present disclosure may further include a third unit, and the third unit includes one or more light-emitting layers between the second unit and the cathode. One or more charge generation layers may be included between the second unit and the third unit. The third unit may include a third hole injection layer formed on the charge generation layer, a third hole transport layer formed on the third hole injection layer, a third light-emitting layer formed on the third hole transport layer, a third electron transport layer formed on the third light-emitting layer, and a third electron injection layer formed on the third electron transport layer. The third hole injection layer, the third hole transport layer, the third light-emitting layer, the third electron transport layer, and the third electron injection layer may each be a single layer or multiple layers.

[0281] According to an embodiment of the present disclosure, the organic electroluminescent device of the present disclosure includes an anode, a cathode, a plurality of light-emitting layers between the anode and the cathode, and at least one charge generation layer between the plurality of light-emitting layers. At least one of the plurality of light-emitting layers contains the compound represented by Formula 1 of the present disclosure. According to an embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may be a white organic electroluminescent device. In the case of a white organic electroluminescent device, a color filter or other known color realization means may be used to realize the color.

[0282] The charge generation layer (CGL) is generally composed of a junction structure of an electron transport layer doped with an alkali metal and a material having a very low LUMO energy level, which greatly affects the overall characteristics of the device. According to one embodiment of the present disclosure, the charge generation layer refers to pCGL (e.g., HATCN, V2O5, WO3, MoO3, etc.), which generates and transports charges, and it is used together with nCGL (e.g., Li, Mg, Ca, etc.) to effectively transport the generated electrons to the electron transport layer.

[0283] The structure of the organic electroluminescent device of the present disclosure is not limited to the above examples, and a variety of light-emitting materials emitting different colors can be arranged in the stacking direction of the layers constituting the device, or a variety of light-emitting materials can be mixed to generate white light.

[0284] To form each layer of the organic electroluminescent device of the present disclosure, dry film-forming methods such as vacuum evaporation, sputtering, plasma, and ion plating methods, or wet film-forming methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating methods can be used. The compounds of the present disclosure can be co-evaporated or mixed-evaporated.

[0285] When using the wet film-forming method, a thin film can be formed by dissolving or diffusing the material for forming each layer in any suitable solvent (such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent can be any solvent in which the material for forming each layer can be dissolved or diffused and there is no problem in film-forming ability.

[0286] In addition, a display system or a lighting system can be produced by using the organic electroluminescent device of the present disclosure. Specifically, a display system, such as a display system for a smartphone, a tablet computer, a laptop computer, a PC, a TV, or an automobile, or a lighting system, such as an outdoor or indoor lighting system, can be produced by using the organic electroluminescent device of the present disclosure.

[0287] Hereinafter, the characteristics of the OLED containing the compound according to the present disclosure will be explained in detail.

[0288] Device Example 1: Production of OLEDs by Deposition of Host Compounds According to the Disclosure

[0289] The OLED is produced as follows using the organic electroluminescent compound according to the present disclosure: The indium tin oxide (ITO) thin film (10 Ω / sq) (Samsung-Corning GEOMATEC CO., LTD.) on the glass substrate used for the OLED is subjected to ultrasonic washing successively with acetone, ethanol, and distilled water, and then stored in isopropyl alcohol. The ITO substrate is mounted on the substrate holder of a vacuum vapor deposition device. The compound HI-1 is introduced into the chamber of the vacuum vapor deposition device, and then the pressure in the chamber of the device is controlled to 10-6 Then, an electric current is applied to the chamber to evaporate the above-introduced material, thereby forming a first hole injection layer with a thickness of 5 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole injection layer with a thickness of 75 nm on the first hole injection layer. Then, compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 5 nm on the second hole injection layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is formed thereon as follows: Compound BH-1 is introduced as a host into one chamber of the vacuum vapor deposition apparatus, and compound BD-1 is introduced as a dopant into another chamber. The two materials are evaporated at different rates such that the dopant is deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form a first light-emitting layer (blue light-emitting layer) with a thickness of 10 nm on the first hole transport layer. As the second light-emitting layer, compound C-8 of the present disclosure is introduced as a host into one chamber of the vacuum vapor deposition apparatus, and compound RD-1 is introduced as a dopant into another chamber. The two materials are evaporated at different rates such that the dopant is deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a second light-emitting layer (red light-emitting layer) with a thickness of 5 nm on the first light-emitting layer. Next, as the third light-emitting layer, compound GH-1 and compound GH-2 are introduced as hosts at a ratio of 1:1 into two chambers of the vacuum vapor deposition apparatus, and compound GD-1 is introduced as a dopant into another chamber. The materials are evaporated at different rates such that the dopant is deposited at a doping amount of 12 wt% based on the total amount of the host and the dopant to form a third light-emitting layer (green light-emitting layer) with a thickness of 22.5 nm on the second light-emitting layer. Compound ET-1 is introduced into another chamber of the vapor deposition apparatus and deposited on the third light-emitting layer to have a thickness of 35 nm as an electron transport layer. After depositing compound EI-1 with a thickness of 2 nm as an electron injection layer on the electron transport layer, an Al cathode with a thickness of 100 nm is deposited on the electron injection layer through another vacuum vapor deposition apparatus. Thus, an OLED is produced.

[0290] The driving voltage, luminous efficiency, power efficiency, external quantum efficiency (EQE), and CIE color coordinates of the OLED produced in the device example are shown in Table 1 below at a current density of 10 mA / cm 2 current density.

[0291] [Table 1]

[0292]

[0293] Comparative example: OLED production by deposition of conventional compounds

[0294] The following is the production of an OLED not according to the present disclosure: The indium tin oxide (ITO) thin film (10 Ω / sq) (Samsung Corning Gioia Co., Ltd.) on the glass substrate used for the OLED is subjected to ultrasonic washing successively with acetone, ethanol, and distilled water, and then stored in isopropyl alcohol. The ITO substrate is mounted on the substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 is introduced into the chamber of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus is controlled to 10 -6Then, an electric current is applied to the chamber to evaporate the above-introduced material, thereby forming a hole injection layer 1-1 with a thickness of 5 nm on the ITO substrate. Next, compound HI-2 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a hole injection layer 1-2 with a thickness of 75 nm on the hole injection layer 1-1. Then, compound HT-1 is introduced into another chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a first hole transport layer with a thickness of 5 nm on the hole injection layer 1-2. After forming the hole injection layer and the hole transport layer, the light-emitting layer is formed thereon as follows: Compound BH-1 is introduced as a host into one chamber of the vacuum vapor deposition apparatus, and compound BD-1 is introduced as a dopant into another chamber. The two materials are evaporated at different rates such that the dopant is deposited at a doping amount of 2 wt% based on the total amount of the host and the dopant to form a first light-emitting layer (blue light-emitting layer) with a thickness of 20 nm on the first hole transport layer. Compound ET-2 is introduced into another chamber of the vapor deposition apparatus and deposited as a first electron transport layer with a thickness of 30 nm. Next, compound CGL is doped with lithium in an amount of 2 wt% as the first charge generation layer. Compound HI-1 is deposited as a second charge generation layer with a thickness of 5 nm on the first charge generation layer. Next, compound HI-2 is deposited as a second hole injection layer with a thickness of 25 nm on the second charge generation layer. Compound HT-2 is introduced into the chamber of the vacuum vapor deposition apparatus, and the compound is evaporated by applying an electric current to the chamber, thereby forming a second hole transport layer with a thickness of 5 nm on the second hole injection layer. As the second light-emitting layer, compound RH and dopant compound RD-1 are simultaneously evaporated at different rates such that the dopant is deposited at a doping amount of 3 wt% based on the total amount of the host and the dopant to form a second light-emitting layer (red light-emitting layer) with a thickness of 10 nm on the second hole transport layer. Next, as the third light-emitting layer, compound GH-1 and compound GH-2 are introduced as hosts into two chambers of the vacuum vapor deposition apparatus at a ratio of 1:1, and compound GD-1 is introduced as a dopant into another chamber. The materials are evaporated at different rates such that the dopant is deposited at a doping amount of 12 wt% based on the total amount of the host and the dopant to form a third light-emitting layer (green light-emitting layer) with a thickness of 45 nm on the second light-emitting layer, where each host is deposited at a ratio of 1:1. Compound ET-1 is deposited as a second electron transport layer with a thickness of 35 nm. After depositing compound EI-1 as a second electron injection layer with a thickness of 2 nm, an Al cathode with a thickness of 100 nm is deposited by another vacuum vapor deposition apparatus. Thus, the OLED is produced.

[0295] Device Examples 2 to 7: Production of OLEDs by Depositing Compounds According to the Disclosure as Hosts for the Second Emitting Layer

[0296] An OLED was produced in the same manner as in the comparative example, except that the host compound described as the host material in Table 2 was used instead of compound RH.

[0297] The following Table 2 shows the driving voltage, luminous efficiency, power efficiency, external quantum efficiency (EQE), and CIE color coordinates of the above-produced OLED at a current density of 10 mA / cm 2 current density.

[0298] [Table 2]

[0299]

[0300] It can be confirmed from the above Table 2 that the OLED containing the compound according to the present disclosure as the second host material is superior in terms of driving voltage, luminous efficiency, external quantum efficiency, and CIE color coordinate characteristics compared to the OLED containing a conventional compound as the second host.

[0301] In addition, Figure 3 and 4 shows the intensity according to wavelength of the OLEDs produced in the comparative example and Device Examples 2 to 7 of the present disclosure. The OLEDs produced in the comparative example and Device Examples 2 to 7 include fluorescent blue light emission and have three peaks of emission wavelengths using phosphorescent red and phosphorescent green light-emitting layers. By using the compound represented by Formula 1 of the present disclosure as the red light-emitting host, the red light-emitting host and the hole transport layer can be configured adjacent to each other. This is considered to improve the charge recombination efficiency because the holes and electrons in the red light-emitting layer can be balanced. The increase in red light emission can improve the external quantum efficiency of the OLED.

[0302] The compounds used in the device examples and the comparative example are shown below.

[0303]

Claims

1. An organic electroluminescent device, which includes an anode, a cathode, and a plurality of light-emitting layers between the anode and the cathode, wherein at least one of the plurality of light-emitting layers contains a compound represented by Formula 1: Wherein M represents O or S; X1 to X 12 each independently represents N or CR1; La represents a single bond, a substituted or unsubstituted (C1-C30) alkylene group, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (3- to 30-membered) heteroarylene group, or a substituted or unsubstituted (C3-C30) cycloalkylene group; X1 to X8, X 11 and X 12 wherein Ar and R1 each independently represent hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri(C1-C30) alkylsilyl, substituted or unsubstituted di(C1-C30) alkyl(C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi(C6-C30)arylsilyl, substituted or unsubstituted or two or more adjacent Ar may be linked to each other to form one or more rings, and two or more adjacent R1 may be linked to each other to form one or more rings; wherein if a plurality of R1 are present, each R1 may be the same or different; and X9 and X 10 Each of R1 in 10 independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, a substituted or unsubstituted (C3-C30) cycloalkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted tris(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl group, a substituted or unsubstituted tris(C6-C30)arylsilyl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino group; a represents an integer of 1 or 2, wherein if a is the integer 2, each Ar may be the same or different.

2. The organic electroluminescent device according to claim 1, wherein, The substituted (C1-C30) (ene) alkyl group, the substituted (C6-C30) (ene) aryl group, the substituted (3- to 30-membered) (ene) heteroaryl group, the substituted (C3-C30) (ene) cycloalkyl group, the substituted (C1-C30) alkoxy group, the substituted tri(C1-C30) alkylsilyl group, the substituted di(C1-C30) alkyl (C6-C30) arylsilyl group, the substituted (C1-C30) alkyldi(C6-C30) arylsilyl group, the substituted tri(C6-C30) arylsilyl group, the substituted mono- or di-(C1- The substituents of the substituted (C1-C30)alkylamino, the substituted mono- or di-(C6-C30)arylamino, the substituted (C1-C30)alkyl(C6-C30)arylamino, and the substituted (C6-C30)aryl(3- to 30-membered)heteroarylamino are each independently at least one selected from the group consisting of: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30)alkyl; halogenated (C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C1-C30)alkylthio; (C3 ... (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3- to 30-membered)heteroaryl, unsubstituted or substituted by one or more (C6-C30)aryl groups; (C6-C30)aryl, unsubstituted or substituted by one or more (3- to 30-membered)heteroaryl groups; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C (C1-C30)alkylamino; mono- or di-(C6-C30)arylamino which is unsubstituted or substituted by one or more (C1-C30)alkyl groups; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronylcarbonyl; di(C1-C30)alkylboronylcarbonyl; (C1-C30)alkyl(C6-C30)arylboronylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

3. The organic electroluminescent device according to claim 1, wherein Ar represents a substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triazinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted triazolopyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted benzothienopyrimidinyl, substituted or unsubstituted acenaphthopyrimidinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted benzoquinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted benzoquinoxalinyl, substituted or unsubstituted dibenzoquinoxalinyl, substituted or unsubstituted indoloquinoxalinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoquinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted benzoisoquinolinyl, substituted or unsubstituted benzothienopyridyl, substituted or unsubstituted benzofuropyridyl, substituted or unsubstituted triazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzothiazolinyl, substituted or unsubstituted phenanthrimidazolyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted fluorenylphenylamino, substituted or unsubstituted dibenzothienylphenylamino, or substituted or unsubstituted dibenzofuranylphenylamino.

4. The organic electroluminescent device according to claim 1, wherein X1 to X8, or X 11 and X 12 At least two adjacent ones of them are CR1, and two adjacent R1s are connected to each other to form any one of the following Formulae 2 to 6, wherein at least one ring is formed in a compound represented by the formula 1: Wherein R2 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tris(C1-C30)alkylsilyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, substituted or unsubstituted tris(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; X represents N or CH; R 11 and R 12 each independently represents hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3- to 30-membered) heteroaryl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group; or R 11 and R 12 may be connected to each other to form one or more rings; and Indicates the junction site between C and R1 in CR1.

5. The organic electroluminescent device according to claim 1, wherein The formula 1 is represented by any one of the following formulas 7 to 10: wherein, X1 to X 12 , and M are as defined in claim 1. The organic electroluminescent device according to claim 1 , wherein: The compound represented by the formula 1 is at least one selected from the following compounds:

7. The organic electroluminescent device according to claim 1, wherein: The organic electroluminescent device includes at least one charge generation layer, and the charge generation layer is located between the light emitting layers.

8. The organic electroluminescent device according to claim 1, wherein, The organic electroluminescent device emits white light.

9. The organic electroluminescent device according to claim 1, wherein: The organic electroluminescent device includes a first unit, a charge generation layer, and a second unit; The first unit is located between the anode and the cathode and includes one or more light emitting layers; The charge generation layer is located between the first unit and the cathode; The second unit is located between the charge generation layer and the cathode and includes one or more light-emitting layers; and At least one of the one or more light-emitting layers included in the first unit and the one or more light-emitting layers included in the second unit contains a compound represented by Formula 1.

10. The organic electroluminescent device according to claim 9, further comprising a third unit, wherein the third unit is located between the second unit and the cathode and includes one or more light-emitting layers.

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