阅读说明：本技术 新型化合物及利用其的有机发光器件 (Novel compound and organic light emitting device using the same ) 是由 李多情 李东勋 金旼俊 徐尚德 金永锡 吴重锡 金恩镐 李勇翰 于 2020-08-13 设计创作，主要内容包括：本发明提供新型化合物及利用其的有机发光器件。(The invention provides a novel compound and an organic light emitting device using the same.)

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

x is O or S, and X is O or S,

l is a single bond; substituted or unsubstituted C_6-60An arylene group; or substituted or unsubstituted comprisesN, O and C containing 1 or more hetero atoms in S_2-60A heteroarylene group, a heteroaryl group,

ar is substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S_2-60(ii) a heteroaryl group, wherein,

R₁and R₂Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amine group; substituted or unsubstituted C_1-60An alkyl group; substituted or unsubstituted C_3-60A cycloalkyl group; substituted or unsubstituted C_2-60An alkenyl group; substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S_2-60(ii) a heteroaryl group, wherein,

a and b are each independently an integer of 0 to 5.

2. A compound according to claim 1, which is a pharmaceutically acceptable salt thereof,

wherein L is a single bond, phenylene, biphenyldiyl or naphthylene.

3. A compound according to claim 1, which is a pharmaceutically acceptable salt thereof,

wherein Ar is any one of substituents represented by the following chemical formulae 2a to 2 d:

in the chemical formulas 2a to 2d,

y is O or S, and Y is O or S,

each Z is independently N or CH, however, at least one of Z is N,

r, R' and R "are each independently hydrogen; deuterium; c_6-20An aryl group; or C containing 1 or more heteroatoms selected from N, O and S_2-20(ii) a heteroaryl group, wherein,

wherein said R, R 'and R' are unsubstituted; or is selected from deuterium, C_6-20Aryl, or C substituted by deuterium_6-201 or more substituents in the aryl group,

m is an integer of 0 to 4.

4. A compound according to claim 3, wherein said compound is selected from the group consisting of,

wherein R and R' are each independently phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl,

wherein R and R' are unsubstituted; or substituted with 1 or more substituents selected from deuterium, phenyl, and phenyl substituted with deuterium.

5. A compound according to claim 3, wherein said compound is selected from the group consisting of,

wherein R' is hydrogen or deuterium.

6. A compound according to claim 1, which is a pharmaceutically acceptable salt thereof,

wherein Ar is a substituent represented by any one of the following chemical formulae:

among the substituents mentioned above, the group of the substituted,

y is O or S, and Y is O or S,

r and R' are each independently phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl,

wherein R and R' are unsubstituted; or substituted with 1 or more substituents selected from deuterium, phenyl, and phenyl substituted with deuterium.

7. A compound according to claim 1, which is a pharmaceutically acceptable salt thereof,

wherein R is₁And R₂Each independently hydrogen or deuterium.

8. A compound according to claim 1, which is a pharmaceutically acceptable salt thereof,

wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-4:

chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1 to 3

Chemical formulas 1 to 4

In the chemical formulas 1-1 to 1-4,

y is O or S, and Y is O or S,

each Z is independently N or CH, however, at least one of Z is N,

r and R' are each independently C_6-20An aryl group; or C containing 1 or more heteroatoms selected from N, O and S_2-20(ii) a heteroaryl group, wherein,

wherein R and R' are unsubstituted; or is selected from deuterium, C_6-20Aryl and C substituted by deuterium_6-201 or more substituents in the aryl group,

x and L are as defined in claim 1.

9. A compound according to claim 1, which is a pharmaceutically acceptable salt thereof,

wherein the compound is any one selected from the following compounds:

10. an organic light emitting device, comprising: a first electrode; a second electrode provided so as to face the first electrode; and a light-emitting layer provided between the first electrode and the second electrode, the light-emitting layer containing the compound according to any one of claims 1 to 9.

Technical Field

Cross reference to related applications

The present application claims priority based on korean patent application No. 10-2019-.

The present invention relates to a novel compound and an organic light emitting device comprising the same.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.

An organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.

For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.

Documents of the prior art

Patent document

(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826

Disclosure of Invention

Technical subject

The present invention relates to a novel compound and an organic light emitting device comprising the same.

Means for solving the problems

The present invention provides a compound represented by the following chemical formula 1:

[ chemical formula 1]

In the above-described chemical formula 1,

x is O or S, and X is O or S,

l is a single bond; substituted or unsubstituted C_6-60An arylene group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S_2-60A heteroarylene group, a heteroaryl group,

ar is substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S_2-60(ii) a heteroaryl group, wherein,

R₁and R₂Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amine group; substituted or unsubstituted C_1-60An alkyl group; substituted or unsubstituted C_3-60Cycloalkyl radicals(ii) a Substituted or unsubstituted C_2-60An alkenyl group; substituted or unsubstituted C_6-60An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom of N, O and S_2-60(ii) a heteroaryl group, wherein,

a and b are each independently an integer of 0 to 5,

when a and b are each 2 or more, the substituents in parentheses may be the same or different from each other.

In addition, the present invention provides an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and a light-emitting layer between the first electrode and the second electrode, the light-emitting layer including the compound represented by chemical formula 1.

Effects of the invention

The compound represented by the above chemical formula 1 is used as a material of an organic layer of an organic light emitting device, so that efficiency, driving voltage, and/or life span characteristics of the organic light emitting device may be improved.

Drawings

Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron blocking layer 7, a hole blocking layer 8, an electron injection and transport layer 8, and a cathode 4.

Detailed Description

Hereinafter, the present invention will be described in more detail to assist understanding thereof.

(definition of wording)

In the context of the present specification,represents a bond to other substituents, and D represents deuterium.

In the present specification, the term "substituted or unsubstituted" means substituted with a substituent selected from deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amine group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio (Alkyl thio); arylthio (Aryl thio); alkylsulfonyl (Alkyl sulfonyl); arylsulfonyl (Aryl sulfonyl); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heteroaryl groups containing N, O and S atoms, or substituted or unsubstituted by 2 or more substituents of the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.

In particular, in this specification, the term "substituted with deuterium" means that at least one of the hydrogens (H) within the structure is substituted with deuterium (D). For example, one of the hydrogens in the functional group/substituent structure may be replaced with deuterium, or all hydrogens may be replaced with deuterium, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a n-nonyl group, a 2, 2-dimethylheptyl group, a 1-ethyl-propyl group, a 1, 1-dimethyl-propyl group, a 1-propyl group, a tert-pentyl group, a 2-pentyl group, a hexyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,And a fluorenyl group, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, the compound may beAnd the like. But is not limited thereto.

In the present specification, the heteroaryl group is a heteroaryl group containing 1 or more of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of heteroaryl groups include xanthene, thioxanthene, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl group,Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinylAzolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoylExamples of the heterocyclic group include, but are not limited to, an azole group, a thiadiazole group, a phenothiazine group, and a dibenzofuran group.

In the present specification, the aromatic ring refers to a condensed monocyclic or condensed polycyclic ring containing only carbon as a ring-forming atom and having aromaticity (aromaticity) throughout the molecule. The number of carbon atoms of the aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but the aromatic ring is not limited thereto. The aromatic ring may be a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, or the like, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the aryl group described above. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heteroaryl group. In the present specification, the alkenyl group in the aralkenyl group is the same as exemplified above for the alkenyl group. In the present specification, the arylene group is a 2-valent group, and in addition thereto, the above description about the aryl group can be applied. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heteroaryl group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description on the heteroaryl group can be applied.

(Compound (I))

The present invention provides a compound represented by the above chemical formula 1.

The compound represented by the above chemical formula 1 has a heptagonal nucleus in which positions 1 and 13 of 7H-dibenzo [ c, g ] carbazole are connected by O or S, and a structure in which N atoms contained in the nucleus are substituted with a substituent group-L-Ar.

In particular, in the compound represented by the above chemical formula 1, Ar may be C containing at least 1N atom as described later_2-60Heteroaryl group, when such a compound is used as a host material of a light-emitting layer, the heteroaryl group is bonded to a compound not containing the heptagonal nucleus and a compound having a carbon atom other than one containing at least 1N atom_2-60The energy transfer to the dopant is smoothly achieved compared to the compound of the other Ar substituent of the heteroaryl group, and thus efficiency and lifetime characteristics can be significantly improved while reducing the driving voltage of the organic light emitting device.

Preferably, L may be a single bond, or C unsubstituted or substituted with deuterium_6-20An arylene group. Specifically, C substituted with deuterium as described above_6-20The arylene group may have all hydrogens replaced with deuterium.

More preferably, L may be a single bond, phenylene unsubstituted or substituted with deuterium, biphenyldiyl unsubstituted or substituted with deuterium, or naphthylene unsubstituted or substituted with deuterium.

For example, L may be a single bond or selected from any one of the following groups, but is not limited thereto:

preferably, Ar may be unsubstituted or selected from deuterium and C_6-20C substituted with 1 or more substituents in the aryl radical containing 1 or more heteroatoms in N, O or S and containing at least 1N atom_2-60A heteroaryl group.

More preferably, Ar may be unsubstituted or selected from deuterium and C_6-20A six-membered heteroaryl group containing 1 to 3N atoms substituted with 1 or more substituents in the aryl group; unsubstituted or substituted by deuterium and C_6-20C containing 1 or 2N atoms and 1O atom substituted by more than 1 substituent in aryl group_2-20A heteroaryl group; unsubstituted or substituted by deuterium and C_6-20C containing 1 or 2N atoms and 1S atom substituted by more than 1 substituent in aryl group_2-20A heteroaryl group; or unsubstituted or substituted by deuterium and C_6-20C containing 1 or 2N atoms substituted by more than 1 substituent in aryl_8-20A heteroaryl group.

Specifically, Ar may be any one of substituents represented by the following chemical formulae 2a to 2 d:

in the above chemical formulas 2a to 2d,

y is O or S, and Y is O or S,

each Z is independently N or CH, however, at least one of Z is N,

r, R' and R "are each independently hydrogen; deuterium; c_6-20An aryl group; or C containing 1 or more heteroatoms selected from N, O and S_2-20(ii) a heteroaryl group, wherein,

wherein R is as defined aboveR 'and R' are unsubstituted; or is selected from deuterium, C_6-20Aryl, or C substituted by deuterium_6-201 or more substituents in the aryl group,

m is an integer of 0 to 4.

Preferably, in the above chemical formula 2a, may be

Z are both N, or

One of Z is N and the others are CH, or

Two of Z are N, and the rest are CH.

In addition, in the above chemical formulas 2b to 2c, may be

Z are both N, or

One of Z is N, and the others are CH.

Preferably, in the above chemical formulas 2a to 2d,

r and R' are each independently C_6-20An aryl group; or C containing 1 or more heteroatoms selected from N, O and S_2-20(ii) a heteroaryl group, wherein,

wherein R and R' may be unsubstituted; or is selected from deuterium, C_6-20Aryl and C substituted by deuterium_6-20More than 1 of the aryl groups are substituted, more specifically with 1 to 5 substituents.

In addition, R' may be hydrogen, deuterium or C_6-20And (4) an aryl group.

More preferably, in the above chemical formulas 2a to 2d,

r and R' are each independently phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl,

wherein R and R' may be unsubstituted; or substituted with 1 or more, more specifically 1 to 5 substituents selected from deuterium, phenyl and phenyl substituted with deuterium.

And, R "may be hydrogen or deuterium.

More preferably, in the above chemical formulas 2a to 2d,

r and R' are each independently phenyl, phenyl substituted with 1 to 5 deuterium, biphenyl, naphthyl, 9-phenylcarbazolyl, 9- (phenyl substituted with 1 to 5 deuterium) carbazolyl, dibenzofuranyl, or dibenzothiophenyl,

r "may be hydrogen.

For example, R and R' may each independently be any one selected from the following groups, but are not limited thereto:

preferably, R₁And R₂Each independently is hydrogen or deuterium, and a and b are each independently 0 or 1.

More specifically, Ar may be any one of substituents represented by the following chemical formulae 2a-1 to 2a-4, 2b-1, 2b-2, 2c-1 to 2c-3, 2d-1 and 2 d-2:

in the above chemical formulas 2a-1 to 2a-4, 2b-1, 2b-2, 2c-1 to 2c-3, 2d-1 and 2d-2,

y is O or S, and Y is O or S,

r and R' are each independently phenyl, biphenyl, naphthyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl,

wherein R and R' are unsubstituted; or substituted with 1 or more substituents selected from deuterium, phenyl, and phenyl substituted with deuterium.

Preferably, R₁And R₂May each independently be hydrogen or deuterium.

At this time, R is represented₁A in the number of (a) may be 0, 1,2, 3,4 or 5, and represents R₂The number of (a) may be 0, 1,2, 3,4 or 5.

Specifically, the compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 1A to 1D depending on the structure of the substituent Ar:

[ chemical formula 1-1]

[ chemical formulas 1-2]

[ chemical formulas 1-3]

[ chemical formulas 1 to 4]

In the above chemical formulas 1-1 to 1-4,

y is O or S, and Y is O or S,

each Z is independently N or CH,

r and R' are each independently C_6-20An aryl group; or C containing 1 or more heteroatoms selected from N, O and S_2-20(ii) a heteroaryl group, wherein,

wherein R and R' are unsubstituted; or is selected from deuterium, C_6-20Aryl and C substituted by deuterium_6-201 to 5 substituents in the aryl group,

x and L are the same as defined in the above chemical formula 1.

For example, the compound is any one selected from the following compounds:

on the other hand, as an example, the compound represented by the above chemical formula 1 may be produced by a production method as shown in the following reaction formula 1.

[ reaction formula 1]

In the above reaction formula 1, X "is a halogen, preferably bromine or chlorine, and the definition of other substituents is the same as that described above.

Specifically, the compound represented by the above chemical formula 1 is produced by combining the starting materials SM1 and SM2 through an amine substitution reaction. Such amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base. The reactive group used in the amine substitution reaction may be appropriately changed, and the method for producing the compound represented by chemical formula 1 may be further embodied in the production examples described below.

(organic light emitting device)

In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and a light-emitting layer between the first electrode and the second electrode, the light-emitting layer including the compound represented by chemical formula 1.

In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which the first electrode is an anode and the second electrode is a cathode, and the anode, 1 or more organic layers, and the cathode are sequentially stacked on the substrate (normal type). In addition, the organic light emitting device according to the present invention may be an inverted (inverted) type organic light emitting device in which the first electrode is a cathode and the second electrode is an anode, and the cathode, 1 or more organic layers, and the anode are sequentially stacked on the substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.

Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.

Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron blocking layer 7, a hole blocking layer 8, an electron injection and transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.

In the organic light-emitting device according to the present invention, in addition to the above-mentioned light-emitting layer containing the compound according to the present invention and being manufactured by the method as described above, it can be manufactured by using materials and methods known in the art.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, the following production can be performed: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer.

In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.

In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO₂A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thia-nePhen]Conductive compounds such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, an effect of injecting holes from an anode, and an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron-injecting layer or an electron-injecting material, and having an excellent thin-film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive compounds.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive compounds, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The organic light emitting device according to an embodiment may further include an electron blocking layer on the hole transport layer. The electron blocking layer is a layer including: the layer is formed on the hole transport layer, preferably in contact with the light-emitting layer, and serves to prevent excessive electron transfer by adjusting hole mobility, thereby increasing the probability of hole-electron combination, and thus improving the efficiency of the organic light-emitting device. The electron blocking layer includes an electron blocking material, and examples of such an electron blocking material include, but are not limited to, the compound represented by chemical formula 1, and arylamine-based organic materials.

The light emitting layer may include a host material and a dopant material. As the host material, the compound represented by the above chemical formula 1 may be used. In addition, as the host material, in addition to the compound represented by the above chemical formula 1, an aromatic fused ring derivative, a heterocyclic ring-containing compound, or the like may be further used. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.

Further, as the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

More specifically, as the dopant material, the following compounds can be used, but the dopant material is not limited thereto:

in addition, the organic light emitting device according to an embodiment may further include a hole blocking layer on the light emitting layer. The hole blocking layer is a layer including: the layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and serves to prevent excessive hole migration by adjusting the electron mobility, thereby increasing the probability of hole-electron combination and improving the efficiency of the organic light-emitting device. The hole-blocking layer contains a hole-blocking substance, and examples of such hole-blocking substances include triazine derivatives, triazole derivatives, and the like,Examples of the compound to which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives.

The electron injection and transport layer is a layer that injects electrons from the electrode, transports the received electrons to the light-emitting layer, and functions as an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such an electron injecting and transporting substance is a substance that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having a high mobility to electrons. As a specific electron injectionAnd transport materials, such as Al complexes of 8-hydroxyquinoline, containing Alq₃The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, a triazine derivative, etc., but are not limited thereto. Or with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like are used together, but the present invention is not limited thereto.

The above-mentioned electron injection and transport layer may also be formed as separate layers such as an electron injection layer and an electron transport layer. In this case, an electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron injecting and transporting substance can be used as an electron transporting substance contained in the electron transport layer. Further, an electron injection layer is formed on the electron transport layer, and LiF, NaCl, CsF, Li, or the like can be used as an electron injection substance contained in the electron injection layer₂O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,Azole,Oxadiazole, triazole, imidazole, benzimidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like.

Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.

In addition, the compound according to the present invention may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.

The manufacture of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.

Synthesis example 1: production of Compound 1

Substance 1(10g, 37.4mmol), compound a (11.6g, 41.1mmol), sodium tert-butoxide (7.2g, 74.7mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.4g, 0.7mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.2g of compound 1. (yield 64%, MS: [ M + H ]]⁺＝513)。

Synthesis example 2: production of Compound 2

Under nitrogen atmosphere, material 2(10g, 36mmol), Compound a (11.1g, 39.6mmol), sodium tert-butoxide (6.9g, 72 m)mol) are added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.4g, 0.7mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.8g of compound 2. (yield 52%, MS: [ M + H ]]⁺＝523)

Synthesis example 3: production of Compound 3

Under a nitrogen atmosphere, substance 3(10g, 23.1mmol), compound a (7.1g, 25.4mmol), sodium tert-butoxide (4.4g, 46.2mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8g of compound 3. (yield 51%, MS: [ M + H ]]⁺＝678)。

Synthesis example 4: production of Compound 4

Under a nitrogen atmosphere, substance 4(10g, 17.4mmol), compound a (5.4g, 19.2mmol), sodium tert-butoxide (3.3g, 34.8mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After the reaction was completed in hours, the reaction mixture was cooled to normal temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate wasAnd (5) distilling under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.3g of compound 4. (yield 51%, MS: [ M + H ]]⁺＝819)。

Synthesis example 5: production of Compound 5

Substance 5(10g, 41.5mmol), compound a (12.9g, 45.7mmol), sodium tert-butoxide (8g, 83.1mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.4g, 0.8mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.7g of compound 5. (yield 58%, MS: [ M + H ]]⁺＝486)。

Synthesis example 6: production of Compound 6

Under a nitrogen atmosphere, substance 6(10g, 28.8mmol), compound a (8.9g, 31.7mmol), sodium tert-butoxide (5.5g, 57.7mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.6g of compound 6. (yield 68%, MS: [ M + H ]]⁺＝592)。

Synthesis example 7: production of Compound 7

Substance 7(10g, 24mmol), compound a (7.4g, 26.4mm ol), sodium tert-butoxide (4.6g, 48mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6g of compound 7. (yield 54%, MS: [ M + H ]]⁺＝662)。

Synthesis example 8: production of Compound 8

Under a nitrogen atmosphere, substance 8(10g, 21.9mmol), compound a (6.8g, 24.1mmol), sodium tert-butoxide (4.2g, 43.8mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4g of compound 8. (yield 68%, MS: [ M + H ]]⁺＝702)。

Synthesis example 9: production of Compound 9

Substance 9(10g, 31.6mmol), compound a (9.8g, 34.7mmol), sodium tert-butoxide (6.1g, 63.1mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tritertine) was chargedButylphosphine) palladium (0) (0.3g, 0.6 mmol). After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4g of compound 9. (yield 70%, MS: [ M + H ]]⁺＝562)。

Synthesis example 10: production of Compound 10

Substance 10(10g, 24.6mmol), compound a (7.6g, 27.1mmol), sodium tert-butoxide (4.7g, 49.3mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.7g of compound 10. (yield 54%, MS: [ M + H ]]⁺＝651)。

Synthesis example 11: production of Compound 11

Under a nitrogen atmosphere, substance 11(10g, 21.9mmol), compound a (6.8g, 24.1mmol), sodium tert-butoxide (4.2g, 43.8mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. Purifying the concentrated compound by silica gel column chromatographyThus, 8.6g of Compound 11 was obtained. (yield 56%, MS: [ M + H ]]⁺＝702)。

Synthesis example 12: production of Compound 12

Substance 12(10g, 27.3mmol), compound a (8.4g, 30mmol), sodium tert-butoxide (5.2g, 54.5mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.2g of compound 12. (yield 55%, MS: [ M + H ]]⁺＝612)。

Synthesis example 13: production of Compound 13

Under a nitrogen atmosphere, substance 13(10g, 26.8mmol), compound a (8.3g, 29.5mmol), sodium tert-butoxide (5.2g, 53.6mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3g of compound 13. (yield 56%, MS: [ M + H ]]⁺＝618)。

Synthesis example 14: production of Compound 14

Substance 14(10g, 25.8mmol), compound a (8g, 28.4mmol), sodium tert-butoxide (5g, 51.7mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.8g of compound 14. (yield 66%, MS: [ M + H ]]⁺＝632)。

Synthesis example 15: production of Compound 15

Substance 15(10g, 33.1mmol), compound a (10.3g, 36.4mmol), sodium tert-butoxide (6.4g, 66.3mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.7mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.2g of compound 15. (yield 62%, MS: [ M + H ]]⁺＝547)。

Synthesis example 16: production of Compound 16

Under nitrogen, 16(10g, 20mmol), compound a (6.2g, 22mmol), sodium tert-butoxide (3.9g, 40.1mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. 2 hoursAfter the end of the reaction, the reaction mixture was cooled to normal temperature and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8g of compound 16. (yield 59%, MS: [ M + H ]]⁺＝744)。

Synthesis example 17: production of Compound 17

Substance 17(10g, 17mmol), compound a (5.3g, 18.7mmol), sodium tert-butoxide (3.3g, 34mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6g of compound 17. (yield 61%, MS: [ M + H ]]⁺＝833)。

Synthesis example 18: preparation of Compound 18

Substance 18(10g, 17mmol), compound a (5.3g, 18.7mmol), sodium tert-butoxide (3.3g, 34mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6g of compound 18. (yield 6)8％，MS：[M+H]⁺＝833)。

Synthesis example 19: production of Compound 19

Substance 19(10g, 30.2mmol), compound a (9.4g, 33.3mmol), sodium tert-butoxide (5.8g, 60.5mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.8g of compound 19. (yield 62%, MS: [ M + H ] + ═ 576).

Synthesis example 20: production of Compound 20

Substance 20(10g, 22.4mmol), compound a (6.9g, 24.7mmol), sodium tert-butoxide (4.3g, 44.9mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2g of compound 20. (yield 53%, MS: [ M + H ]]⁺＝691)。

Synthesis example 21: production of Compound 21

Under a nitrogen atmosphere, substance 21(10g, 35mmol), compound a (10.8g, 38.5mmol), sodium tert-butoxide (6.7g, 70mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.4g, 0.7mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.6g of compound 21. (yield 68%, MS: [ M + H ]]⁺＝531)。

Synthesis example 22: preparation of Compound 22

Under a nitrogen atmosphere, substance 22(10g, 24.6mmol), compound a (7.6g, 27mmol), sodium tert-butoxide (4.7g, 49.2mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8g of compound 22. (yield 55%, MS: [ M + H ]]⁺＝652)。

Synthesis example 23: production of Compound 23

Under nitrogen, material 23(10g, 19.5mmol), compound a (6g, 21.4mmol), sodium tert-butoxide (3.7g, 39mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then theAfter the compound was completely dissolved in chloroform again and washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.6g of compound 23. (yield 65%, MS: [ M + H ]]⁺＝758)。

Synthesis example 24: production of Compound 24

Under a nitrogen atmosphere, substance 24(10g, 24.6mmol), compound a (7.6g, 27mmol), sodium tert-butoxide (4.7g, 49.2mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11g of compound 24. (yield 69%, MS: [ M + H ]]⁺＝652)。

Synthesis example 25: production of Compound 25

Under nitrogen, material 25(10g, 29.1mmol), compound a (9g, 32mmol), sodium tert-butoxide (5.6g, 58.2mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.8g of compound 25. (yield 57%, MS: [ M + H ]]⁺＝589)。

Synthesis example 26: preparation of Compound 26

Under nitrogen, material 26(10g, 22.5mmol), compound a (7g, 24.8mmol), sodium tert-butoxide (4.3g, 45.1mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.5mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.4g of compound 26. (yield 54%, MS: [ M + H ]]⁺＝689)。

Synthesis example 27: production of Compound 27

Substance 27(10g, 31.6mmol), compound a (9.8g, 34.7mmol), sodium tert-butoxide (6.1g, 63.1mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.6g of compound 27. (yield 60%, MS: [ M + H ]]⁺＝562)。

Synthesis example 28: preparation of Compound 28

Under nitrogen atmosphere, material 28(10 g)23.6mmol), Compound a (7.3g, 26mmol), sodium tert-butoxide (4.5g, 47.3mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.5mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.5g of compound 28. (yield 54%, MS: [ M + H ]]⁺＝668)。

Synthesis example 29: production of Compound 29

Substance 29(10g, 21.9mmol), compound a (6.8g, 24.1mmol), sodium tert-butoxide (4.2g, 43.8mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.7g of compound 29. (yield 70%, MS: [ M + H ]]⁺＝702)。

Synthesis example 30: production of Compound 30

Under a nitrogen atmosphere, substance 30(10g, 25.4mmol), compound a (7.9g, 27.9mmol), sodium tert-butoxide (4.9g, 50.8mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, and the mixture was usedAfter washing with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.4g of compound 30. (yield 58%, MS: [ M + H ]]⁺＝639)。

Synthesis example 31: production of Compound 31

Substance 31(10g, 25.1mmol), compound a (7.8g, 27.6mmol), sodium tert-butoxide (4.8g, 50.1mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11g of compound 31. (yield 68%, MS: [ M + H ]]⁺＝644)。

Synthesis example 32: production of Compound 32

Under a nitrogen atmosphere, substance 32(10g, 31.5mmol), compound b (10.3g, 34.6mmol), sodium tert-butoxide (6g, 62.9mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 9.3g of compound 32. (yield 51%, MS: [ M + H ]]⁺＝579)。

Synthesis example 33: production of Compound 33

Substance 33(10g, 22.5mmol), compound b (7.4g, 24.8mmol), sodium tert-butoxide (4.3g, 45.1mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.6g of compound 33. (yield 67%, MS: [ M + H ]]⁺＝705)。

Synthesis example 34: preparation of Compound 34

Substance 34(10g, 20mmol), compound b (6.5g, 22mmol), sodium tert-butoxide (3.8g, 40mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.6g of compound 34. (yield 50%, MS: [ M + H ]]⁺＝761)。

Synthesis example 35: production of Compound 35

Under nitrogen atmosphere, substance 35(10g, 31.6mmol), compound b (10.3g, 34.7mmol), tert-butylSodium butoxide (6.1g, 63.1mmol) was added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.5g of compound 35. (yield 63%, MS: [ M + H ]]⁺＝578)。

Synthesis example 36: preparation of Compound 36

Under nitrogen, substance 36(10g, 18.6mmol), compound b (6.1g, 20.5mmol), sodium tert-butoxide (3.6g, 37.2mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.8g of compound 36. (yield 59%, MS: [ M + H ]]⁺＝798)。

Synthesis example 37: production of Compound 37

Substance 37(10g, 34.4mmol), compound b (11.3g, 37.8mmol), sodium tert-butoxide (6.6g, 68.8mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.4g, 0.7mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, and the organic layer was separated and washed with chloroformMagnesium sulfate solution was treated and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.1g of compound 37. (yield 69%, MS: [ M + H ]]⁺＝552)。

Synthesis example 38: production of Compound 38

Under a nitrogen atmosphere, substance 38(10g, 41.5mmol), compound b (13.6g, 45.7mmol), sodium tert-butoxide (8g, 83.1mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.4g, 0.8mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13g of compound 38. (yield 50%, MS: [ M + H ]]⁺＝628)。

Synthesis example 39: preparation of Compound 39

Substance 39(10g, 33.7mmol), compound b (11g, 37.1mmol), sodium tert-butoxide (6.5g, 67.4mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.7mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.4g of compound 39. (yield 66%, MS: [ M + H ]]⁺＝558)。

Synthesis example 40: production of Compound 40

Under nitrogen, material 40(10g, 23.6mmol), compound b (7.7g, 26mmol), sodium tert-butoxide (4.5g, 47.3mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.9g of compound 40. (yield 55%, MS: [ M + H ]]⁺＝684)。

Synthesis example 41: preparation of Compound 41

Material 41(10g, 18.9mmol), compound b (6.2g, 20.8mmol), sodium tert-butoxide (3.6g, 37.8mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 7.8g of compound 41. (yield 52%, MS: [ M + H ]]⁺＝790)。

Synthesis example 42: production of Compound 42

Under nitrogen, substance 42(10g, 21.1mmol), compound b (6.9g, 23.3mmol), sodium tert-butoxide (4.1g, 42.3mmol) were added to 200mlIn xylene, stirring and refluxing. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.2g of compound 42. (yield 53%, MS: [ M + H ]]⁺＝734)。

Synthesis example 43: production of Compound 43

Substance 43(10g, 27mmol), compound b (8.8g, 29.7mmol), sodium tert-butoxide (5.2g, 53.9mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.7g of compound 43. (yield 69%, MS: [ M + H ]]⁺＝632)。

Synthesis example 44: production of Compound 44

Under a nitrogen atmosphere, substance 44(10g, 21.9mmol), compound b (7.2g, 24.1mmol), sodium tert-butoxide (4.2g, 43.8mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.4mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was subjected to reduced pressureAnd (5) distilling. The concentrated compound was purified by silica gel column chromatography to obtain 10.7g of compound 44. (yield 68%, MS: [ M + H ]]⁺＝718)。

Synthesis example 45: production of Compound 45

Substance 45(10g, 17.5mmol), compound b (5.7g, 19.2mmol), sodium tert-butoxide (3.4g, 35mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.3mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8g of compound 45. (yield 55%, MS: [ M + H ]]⁺＝833)。

Synthesis example 46: preparation of Compound 46

Substance 46(10g, 25.5mmol), compound b (8.3g, 28mmol), sodium tert-butoxide (4.9g, 50.9mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.3g of compound 46. (yield 62%, MS: [ M + H ]]⁺＝654)。

Synthesis example 47: preparation of Compound 47

Substance 47(10g, 28mmol), compound b (9.2g, 30.8mmol), sodium tert-butoxide (5.4g, 56.1mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 8.6g of compound 47. (yield 50%, MS: [ M + H ]]⁺＝618)。

Synthesis example 48: preparation of Compound 48

Substance 48(10g, 25.4mmol), compound b (8.3g, 27.9mmol), sodium tert-butoxide (4.9g, 50.8mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11g of compound 48. (yield 66%, MS: [ M + H ]]⁺＝655)。

Synthesis example 49: preparation of Compound 49

Substance 49(10g, 27.3mmol), compound b (8.9g, 30mmol), sodium tert-butoxide (5.2g, 54.5mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, the double is put into(Tri-tert-butylphosphine) palladium (0) (0.3g, 0.5 mmol). After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12g of compound 49. (yield 70%, MS: [ M + H ]]⁺＝628)。

Synthesis example 50: production of Compound 50

Substance 50(10g, 24.6mmol), compound b (8g, 27mmol), sodium tert-butoxide (4.7g, 49.2mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.5mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.2g of compound 50. (yield 62%, MS: [ M + H ]]⁺＝668)。

Synthesis example 51: production of Compound 51

Substance 51(10g, 23.2mmol), compound a (7.2g, 25.5mmol), sodium tert-butoxide (4.4g, 46.3mmol) were added to 200ml of xylene under nitrogen, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.2g, 0.5mmol) was charged. After 3 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. Subjecting the concentrated compound to silica gel column chromatographyPurification was carried out to obtain 8g of compound 51. (yield 51%, MS: [ M + H ]]⁺＝677)。

Synthesis example 52: production of Compound 52

Under a nitrogen atmosphere, substance 52(10g, 31.6mmol), compound b (10.3g, 34.7mmol), sodium tert-butoxide (6.1g, 63.1mmol) were added to 200ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0) (0.3g, 0.6mmol) was charged. After 2 hours the reaction was complete, cooled to ambient temperature and the solvent removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water 2 times, the organic layer was separated, treated with anhydrous magnesium sulfate, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.4g of compound 52. (yield 57%, MS: [ M + H ]]⁺＝578)。

Comparative example 1

Indium Tin Oxide (ITO) and method for producing the sameThe glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode thus prepared, as a hole injection layer, the following HI-1 compound was addedAnd the following a-1 compound was p-doped (p-doping) at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was vacuum-deposited to form a film having a thicknessThe hole transport layer of (1). Then, on the hole transport layer, the film thicknessThe following EB-1 compound was vacuum-evaporated to form an electron blocking layer.

Then, on the electron blocking layer, the following RH-1 compound as a host material and the following Dp-7 compound as a dopant material were vacuum-evaporated at a weight ratio of 98:2 to formA thick red light emitting layer.

On the light-emitting layer, the thickness of the filmA hole-blocking layer was formed by vacuum vapor deposition of the following HB-1 compound. Next, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-evaporated at a weight ratio of 2:1 to form a hole blocking layerThe thickness of (a) forms an electron injection and transport layer.

On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added toThickness of aluminum andis deposited to form a cathode.

In the above process, the evaporation speed of the organic material is maintainedLithium fluoride maintenance of cathodeDeposition rate of (3), aluminum maintenanceThe vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition^-7～5×10^-6And supporting to thereby fabricate an organic light emitting device.

Examples 1 to 52

An organic light-emitting device was produced in the same manner as in comparative example 1, except that the compound shown in table 1 below was used as the host material instead of RH-1 in the organic light-emitting device of comparative example 1.

Comparative examples 2 to 9

An organic light-emitting device was produced in the same manner as in comparative example 1, except that the compound shown in table 1 below was used instead of RH-1 in the organic light-emitting device of comparative example 1.

At this time, the structures of the compounds A to H are shown below.

Experimental example 1: evaluation of device characteristics

When a current was applied to the organic light emitting devices manufactured in the above-described examples 1 to 52 and comparative examples 1 to 9, (10 mA/cm) was measured²Reference) voltage, efficiency, and lifetime, and the results are shown in table 1 below. The lifetime T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

[ Table 1]

As shown in the above table, the organic light emitting device of the example using the compound represented by the above chemical formula 1 as a host material of the red light emitting layer has a low driving voltage, a high efficiency, and a remarkably long life as compared with the organic light emitting device of the comparative example. This is considered to be because the energy transfer to the red dopant was smoothly achieved by the compound represented by the above chemical formula 1, compared to the compound having a structure different from that of the present application used in the comparative example. Therefore, when the compound represented by the above chemical formula 1 is used as a host material of an organic light emitting device, it can be confirmed that the driving voltage, the light emitting efficiency, and/or the lifetime characteristics of the organic light emitting device are improved.

[ description of symbols ]

1: substrate 2: anode

3: light-emitting layer 4: cathode electrode

5: hole injection layer 6: hole transport layer

7: electron blocking layer 8: hole blocking layer

9: an electron injection and transport layer.