CN112028902B - Novel heterocyclic compound and organic light-emitting element using same - Google Patents

Novel heterocyclic compound and organic light-emitting element using same Download PDF

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CN112028902B
CN112028902B CN202010933702.0A CN202010933702A CN112028902B CN 112028902 B CN112028902 B CN 112028902B CN 202010933702 A CN202010933702 A CN 202010933702A CN 112028902 B CN112028902 B CN 112028902B
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CN112028902A (en
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赵圣美
李征夏
李东勋
文程昱
郑珉祐
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LG Chem Ltd
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Abstract

The invention provides a heterocyclic compound and an organic light-emitting device using the same. The compound of the present invention is represented by, for example, chemical formula 1. The compounds of the present invention allow for improved efficiency of organic light emitting elements as well as improved low drive voltage and/or lifetime performance. [ chemical formula 1]
Figure DDA0002671164820000011

Description

Novel heterocyclic compound and organic light-emitting device using the same
The present application is a divisional application of a chinese patent application having an application number of "201710574957.0" on the filing date of 7/14/2017, entitled "novel heterocyclic compound and organic light emitting device using the same".
Technical Field
The present invention relates to a novel heterocyclic compound and an organic light-emitting element comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting element 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 properties, and thus, a great deal of research has been conducted on the organic light emitting element.
An organic light emitting element generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. The organic material layer has a multi-layered structure composed of different materials, respectively, to improve efficiency and stability of the organic light emitting element, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting element, if a voltage is applied between two electrodes, holes are injected from an anode into an organic material layer and electrons are injected from a cathode into the organic material layer, excitons are formed when the injected holes and the electrodes meet, and light is emitted when the excitons return to the ground state again.
As for the organic materials for the organic light emitting element as described above, new materials are continuously required to be developed.
Prior art documents
Patent document 1: korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention provides a novel heterocyclic compound and an organic light-emitting device comprising the same.
Technical scheme
The present invention provides a compound represented by any one of the following chemical formulas 1 to 5:
[ chemical formula 1]
Figure BDA0002671164800000021
[ chemical formula 2]
Figure BDA0002671164800000031
[ chemical formula 3]
Figure BDA0002671164800000032
[ chemical formula 4]
Figure BDA0002671164800000041
[ chemical formula 5]
Figure BDA0002671164800000042
In the chemical formulae 1 to 5,
X 1 to X 3 Are each independently N or CR 11 And X 1 To X 3 At least one of which is N,
Y 1 is O or S, and is a compound of,
L 1 bonding to any of the 1 to 3 positions,
L 1 is a single bond; substituted or unsubstituted C 6-60 An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from O, N, si and S 1-60 A hetero-arylene group,
a1 is an integer of 0 to 3,
Ar 1 to Ar 3 Each independently is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing one to three heteroatoms selected from N, O and S 1-60 (ii) a heteroaryl group, wherein,
R 1 to R 3 And R 11 Each independently is hydrogen; deuterium; a halogen; a cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; c 1-60 A haloalkyl group; substituted or unsubstituted C 1-60 An alkoxy group; substituted or unsubstituted C 1-60 A haloalkoxy group; substituted or unsubstituted C 3-60 A cycloalkyl group; substituted or unsubstituted C 2-60 An alkenyl group; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C 6-60 An aryloxy group; or substituted or unsubstituted containing one or more heteroatoms selected from N, O and SC 1-60 A heterocyclic group,
b1 is an integer of 0 to 4,
b2 is an integer of 0 to 2,
b3 is an integer of 0 to 3.
In addition, the present invention provides an organic light emitting element including: a first electrode; a second electrode opposite the first electrode; and one or more organic material layers between the first electrode and the second electrode, one or more of the organic material layers including a compound represented by any one of chemical formulas 1 to 5.
Effects of the invention
The compound represented by any one of chemical formulas 1 to 5 may be used as a material of an organic material layer of an organic light emitting element, and efficiency, and low driving voltage and/or life span performance may be improved in the organic light emitting element. In particular, the compound represented by any one of chemical formulas 1 to 5 may be used as a host material of a light emitting layer.
Drawings
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
Detailed Description
To facilitate an understanding of the invention, it is described in more detail below.
The present invention provides a compound represented by any one of the chemical formulas 1 to 5.
In the context of the present specification,
Figure BDA0002671164800000061
meaning a bond to other substituents, and a single bond is intended to be L 1 In the absence of other atoms on the moiety.
In the present specification, the term "substituted or unsubstituted" is intended to be 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 amino group; a phosphino group; an alkoxy group; an aryloxy group; alkylsulfoxy (alkylthioaxy group); an arylsulfenoxy group; alkylsulfonyl (alkylsulfonylxy group); an arylsulfonyl group; silyl (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 one or more substituents in a heterocyclic group containing one or more N, O, and S atoms, or substituted or unsubstituted wherein two or more substituents are linked in the indicated substituents. For example, the "substituent to which two or more substituents are linked" may be a biphenyl group. In other words, it is understood that the biphenyl group may be an aryl group, or may be a substituent to which two phenyl groups are attached.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but the number of carbon atoms is preferably 1 to 40. Specifically, the compound may include the following structure, but is not limited thereto.
Figure BDA0002671164800000062
In the present specification, with respect to the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkane group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound of the following structural formula may be included, but not limited thereto.
Figure BDA0002671164800000071
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the compound may include the following structure, but is not limited thereto.
Figure BDA0002671164800000072
In the present specification, the silyl group specifically includes, but is 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, a phenylsilyl group, etc.
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, examples of the halogen group include 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 number of carbon atoms of the alkyl group is from 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is from 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is from 1 to 6. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-methylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.
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 from 2 to 20. According to another embodiment, the number of carbon atoms of said alkenyl group is from 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is from 2 to 6. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl (stilbenyl group), styryl and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms is preferably 3 to 60. According to one embodiment, the number of carbon atoms of said cycloalkyl group is between 3 and 30. According to another embodiment, the number of carbon atoms of said cycloalkyl is comprised between 3 and 20. According to yet another embodiment, the number of carbon atoms of said cycloalkyl group is from 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-methylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the aryl group is not particularly limited, but the number of carbon atoms is preferably 6 to 60, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is from 6 to 30. According to another embodiment, the number of carbon atoms of the aryl group is from 6 to 20. The monocyclic aryl group may include phenyl, biphenyl, terphenyl, and the like, but is not limited thereto. The polycyclic aromatic group may include naphthyl, anthracyl, phenanthryl, pyrenyl, perylenyl, perylene, etc,
Figure BDA0002671164800000092
A phenyl group, a fluorenyl group, and the like, but are not limited thereto.
In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure. When the fluorenyl group is substituted, it may contain
Figure BDA0002671164800000091
And the like, but are not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenonthroline), thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl and the like, but are not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the aforementioned aryl example. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, alkylamino group is the same as in the foregoing examples of the alkyl group. In this specification, the foregoing description of heterocyclic groups may apply to heteroaryl groups in heteroarylamine groups. In the present specification, the alkenyl group in the aralkenyl group is the same as the aforementioned examples of the alkenyl group. In this specification, the foregoing description of aryl groups may apply to arylene groups with the exception of divalent groups. In this specification, the foregoing description of heterocyclic groups applies to heteroarylene groups with the exception of divalent groups. In this specification, the foregoing description of aryl or cycloalkyl groups may apply to hydrocarbon rings, except where a non-monovalent group is formed and two substituents are bonded. In the present specification, the foregoing description of a heterocyclic group may be applied to a heterocyclic ring except for a monovalent group and a group formed by bonding two substituents.
In addition, in the chemical formula 1, when L 1 When bonded to the 1 position, 2 position, or 3 position, the compound may be represented by the following chemical formula 1-1, 1-2, or 1-3, respectively.
[ chemical formula 1-1]
Figure BDA0002671164800000101
[ chemical formulas 1-2]
Figure BDA0002671164800000102
[ chemical formulas 1-3]
Figure BDA0002671164800000111
In the chemical formulas 1-1 to 1-3,
X 1 to X 3 、Y 1 、L 1 、a1、Ar 1 To Ar 3 、R 1 To R 3 、R 11 And b1 to b3 are the same as defined in the chemical formula 1.
In addition, in the chemical formula 2, when L 1 When bonded to the x 1 position, the x 2 position, or the x 3 position, the compound may be represented by the following chemical formula 2-1, 2-2, or 2-3, respectively.
[ chemical formula 2-1]
Figure BDA0002671164800000112
[ chemical formula 2-2]
Figure BDA0002671164800000121
[ chemical formulas 2-3]
Figure BDA0002671164800000122
In the chemical formulas 2-1 to 2-3,
X 1 to X 3 、Y 1 、L 1 、a1、Ar 1 To Ar 3 、R 1 To R 3 、R 11 And b1 to b3 are the same as defined in the chemical formula 2.
In addition, in the chemical formula 3, when L 1 When bonded to the x 1 position, the x 2 position, or the x 3 position, the compound may be represented by the following chemical formula 3-1, 3-2, or 3-3, respectively.
[ chemical formula 3-1]
Figure BDA0002671164800000131
[ chemical formula 3-2]
Figure BDA0002671164800000132
[ chemical formulas 3-3]
Figure BDA0002671164800000133
In the chemical formulas 3-1 to 3-3,
X 1 to X 3 、Y 1 、L 1 、a1、Ar 1 To Ar 3 、R 1 To R 3 、R 11 And b1 to b3 are the same as defined in the chemical formula 3.
In addition, in the chemical formula 4, when L 1 When bonded to the 1 position, 2 position, or 3 position, the compound may be represented by the following chemical formula 4-1, 4-2, or 4-3, respectively.
[ chemical formula 4-1]
Figure BDA0002671164800000141
[ chemical formula 4-2]
Figure BDA0002671164800000142
[ chemical formulas 4-3]
Figure BDA0002671164800000151
In the chemical formulas 4-1 to 4-3,
X 1 to X 3 、Y 1 、L 1 、a1、Ar 1 To Ar 3 、R 1 To R 3 、R 11 And b1 to b3 are the same as defined in the chemical formula 4.
In addition, in the chemical formula 5, when L 1 When bonded to the 1 position, 2 position, or 3 position, the compound may be represented by the following chemical formula 5-1, 5-2, or 5-3, respectively.
[ chemical formula 5-1]
Figure BDA0002671164800000152
[ chemical formula 5-2]
Figure BDA0002671164800000161
[ chemical formulas 5-3]
Figure BDA0002671164800000162
In the chemical formulas 5-1 to 5-3,
X 1 to X 3 、Y 1 、L 1 、a1、Ar 1 To Ar 3 、R 1 To R 3 、R 11 And b1 to b3 are the same as defined in said chemical formula 5.
Thus, in the chemical formulas 1 to 5, if L 1 Bonded to the x 1 site, the x 2 site, or the x 3 site, the compound can improve the efficiency of the organic light emitting element and improve low driving voltage and/or lifetime performance when used as a host material of the organic light emitting element.
In contrast, in the chemical formulas 1 to 5, L 1 With other positions (e.g. 4-positions) than* When a compound bonded at a 1-position, a 2-position, or a 3-position is used as a host material of an organic light emitting element, there is a limitation in that the life performance of the organic light emitting element is drastically reduced.
This is because the bond between the Oxygen (Oxygen) atom of indole dibenzofuran (indole dibenzofuran) belonging to HOMO and the Oxygen (Oxygen) atom belonging to LUMO is connected to L 1 Aromatic functional group (containing Ar) 2 And Ar 3 ) In the same direction, the Dipole moment (Dipole moment) of the compound becomes large, and the transport property is relatively lowered, and further the balance (balance) of holes and electrons inside the light emitting layer is lowered. In addition, non-bonding electrons (non-bonding electrons) are bonded to L via the Oxygen (Oxygen) atom of the indole dibenzofuran 1 The stability of the compound may be reduced by the repulsion of non-bonded electrons or adjacent hydrogens of the aromatic functional groups of (a).
In the chemical formulae 1 to 5,
X 1 can be N, X 2 Can be N, X 3 Can be N; or alternatively
X 1 Can be N, X 2 Can be N, X 3 May be CR 11 (ii) a Or alternatively
X 1 Can be N, X 2 May be CR 11 ，X 3 Can be N; or
X 1 May be CR 11 ，X 2 Can be N, X 3 Can be N; or alternatively
X 1 Can be N, X 2 Can be CR 11 ，X 3 Can be CR 11 (ii) a Or
X 1 Can be CR 11 ，X 2 Can be N, X 3 May be CR 11 (ii) a Or alternatively
X 1 May be CR 11 ，X 2 Can be CR 11 ，X 3 May be N.
According to an embodiment, Y 1 May be O.
According to an embodiment, L 1 May be bonded to the x 1 position. Thus, the compound may be a compound represented by the chemical formula 1-1, 2-1, or 3-1.
According to an embodiment, L 1 Can be a single bond; substituted or unsubstituted C 6-20 An arylene group; or substituted or unsubstituted C containing one or two N 1-20 A heteroarylene group.
For example, L 1 Can be a single bond; c unsubstituted or substituted by deuterium, fluoro or cyano 6-20 An arylene group; or C unsubstituted or substituted by deuterium, fluoro or cyano 1-20 A heteroarylene group.
Specifically, for example, L 1 May be a single bond or may be any one selected from the group:
Figure BDA0002671164800000181
more specifically, for example, L 1 May be a single bond or may be any one selected from the group:
Figure BDA0002671164800000182
according to one embodiment, a1 may be 0, 1, or 2. In this case, a1 represents L 1 If a1 is 2 or more, L is 2 or more 1 May be the same or different. Further, if a1 is 0, it represents L 1 Is a single bond.
According to one embodiment, ar 1 C which may be substituted or unsubstituted 6-60 And (4) an aryl group.
For example, ar 1 Phenyl which may be substituted or unsubstituted; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl group; substituted or unsubstituted phenanthryl; substituted or unsubstituted anthracenyl; a substituted or unsubstituted fluoranthenyl group; substituted or unsubstituted triphenylene (triphenylenyl group); a substituted or unsubstituted pyrenyl group; or substituted or unsubstituted
Figure BDA0002671164800000192
A group (crycenyl).
In particular, it relates toFor example, ar 1 May be any one selected from the group:
Figure BDA0002671164800000191
in the chemical formula, the compound represented by the formula,
Z 1 to Z 4 Each independently is hydrogen; deuterium; a halogen; a cyano group; a nitro group; an amino group; c 1-20 An alkyl group; c 1-20 A haloalkyl group; or C 6-20 An aryl group which is a radical of an aromatic group,
c1 is an integer of 0 to 5,
c2 is an integer of 0 to 7,
c3 is an integer of 0 to 9,
c4 is an integer of 0 to 4,
c5 is an integer of 0 to 3.
In the above, Z 1 To Z 4 Each independently may be hydrogen or phenyl, and c1 to c5 each independently may be 0 or 1.
More specifically, for example, ar 1 May be any one selected from the group of:
Figure BDA0002671164800000201
according to one embodiment, ar 2 And Ar 3 Each independently may be substituted or unsubstituted C 6-20 An aryl group; or substituted or unsubstituted C containing a heteroatom selected from N, O and S 1-20 A heteroaryl group.
For example, ar 2 And Ar 3 Each independently may be a substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl group; substituted or unsubstituted phenanthryl; a substituted or unsubstituted anthracyl group; substituted or unsubstituted fluoranthenyl; substituted or unsubstituted triphenylene; substituted or unsubstituted pyrenyl; substituted or unsubstituted
Figure BDA0002671164800000212
A group; substituted or unsubstituted carbazolyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothienyl; substituted or unsubstituted pyridyl; a substituted or unsubstituted pyrazinyl group; substituted or unsubstituted pyrimidinyl; a substituted or unsubstituted pyridazinyl group; or a substituted or unsubstituted triazolyl group.
Specifically, for example, ar 2 And Ar 3 Each independently may be any one selected from the group:
Figure BDA0002671164800000211
in the chemical formula, the compound represented by the formula,
Z 11 to Z 14 Each independently is hydrogen; deuterium; halogen; a cyano group; a nitro group; an amino group; c 1-20 An alkyl group; c 6-20 An aryl group; or C containing one to three N 1-20 (ii) a heteroaryl group, wherein,
c11 is an integer of 0 to 5,
c12 is an integer of 0 to 7,
c13 is an integer of 0 to 3,
c14 is an integer of 0 to 4.
In the above, Z 11 To Z 14 Each independently can be hydrogen; a fluorine group; a cyano group; a methyl group; a phenyl group; a naphthyl group; or pyridyl, each of c11 to c14 independently can be 0, 1, or 2.
More specifically, for example, ar 2 And Ar 3 Each independently may be any one selected from the group:
Figure BDA0002671164800000221
Figure BDA0002671164800000231
according to one embodiment, R 1 To R 3 And R 11 Each independently can be hydrogen; deuterium; a halogen; a cyano group; a nitro group; an amino group; c 1-20 An alkyl group; or C 6-20 And (4) an aryl group.
For example, R 1 To R 3 And R 11 Each independently can be hydrogen; deuterium; a halogen; a cyano group; a nitro group; an amino group; a methyl group; or a phenyl group.
Specifically, for example, R 1 To R 3 May be hydrogen, and each of b1 to b3 independently may be 0 or 1.
Furthermore, R 11 Can be hydrogen; deuterium; a fluorine group; or a cyano group.
In this case, b1 represents R 1 If b1 is 2 or more, R is 2 or more 1 May be the same or different. For b2 and b3, the description of b1 and the structures of chemical formulas 1 to 5 can be referred to.
In addition, c1 represents Z 1 If c1 is 2 or more, Z is 2 or more 1 May be the same or different. For c2 to c5 and c11 to c14, reference may be made to the description of c1 and the structure of the chemical formula.
In addition, the compound may be any one compound selected from the group consisting of compounds represented by the following chemical formulas 1-1-1 to 5-1-1:
[ chemical formula 1-1-1]
Figure BDA0002671164800000241
[ chemical formula 2-1-1]
Figure BDA0002671164800000242
[ chemical formula 3-1-1]
Figure BDA0002671164800000251
[ chemical formula 4-1-1]
Figure BDA0002671164800000252
[ chemical formula 5-1-1]
Figure BDA0002671164800000261
In the chemical formulas 1-1-1 to 5-1-1,
X 1 to X 3 、R 1 、L 1 A1, b1 and Ar 1 To Ar 3 The definitions of (a) are the same as those described above.
For example, the compound may be selected from the following compounds.
Figure BDA0002671164800000262
Figure BDA0002671164800000271
Figure BDA0002671164800000281
Figure BDA0002671164800000291
Figure BDA0002671164800000301
Figure BDA0002671164800000311
Figure BDA0002671164800000321
Figure BDA0002671164800000331
Figure BDA0002671164800000341
Figure BDA0002671164800000351
Figure BDA0002671164800000361
Figure BDA0002671164800000371
Figure BDA0002671164800000381
Figure BDA0002671164800000391
Figure BDA0002671164800000401
Figure BDA0002671164800000411
Figure BDA0002671164800000421
Figure BDA0002671164800000431
Figure BDA0002671164800000441
Figure BDA0002671164800000451
Figure BDA0002671164800000461
Figure BDA0002671164800000471
Figure BDA0002671164800000481
Figure BDA0002671164800000491
Figure BDA0002671164800000501
Figure BDA0002671164800000511
Figure BDA0002671164800000521
Figure BDA0002671164800000531
Figure BDA0002671164800000541
Figure BDA0002671164800000551
Figure BDA0002671164800000561
Figure BDA0002671164800000571
Figure BDA0002671164800000581
Figure BDA0002671164800000591
Figure BDA0002671164800000601
Figure BDA0002671164800000611
Figure BDA0002671164800000621
Figure BDA0002671164800000631
Figure BDA0002671164800000641
Figure BDA0002671164800000651
Figure BDA0002671164800000661
Figure BDA0002671164800000671
Figure BDA0002671164800000681
Figure BDA0002671164800000691
Figure BDA0002671164800000701
Figure BDA0002671164800000711
Since the compound represented by any one of the chemical formulas 1 to 5 has a structure in which an N atom-containing heteroaryl substituent such as a pyridyl group, a pyrimidyl group, or a triazinyl group is bonded to a specific position of an indole dibenzofuran or indole dibenzothiophene (indole dibenzothiophene) core, an organic light-emitting element using the compound can have high efficiency, low driving voltage, high luminance, long lifetime, and the like.
For the compound represented by the chemical formula 1-1-1, it can be prepared, for example, by a preparation method such as the following reaction formula 1.
[ reaction formula 1]
Figure BDA0002671164800000721
In the reaction formula 1, X 1 To X 3 、L 1 A1, and Ar 1 To Ar 3 Is the same as the chemical formula 1, and X represents halogen.
Further, as for the compound represented by any one of the chemical formulas 1 to 5, it can be prepared by referring to the reaction formula 1 and appropriately substituting the starting materials in accordance with the structure of the compound to be prepared.
In addition, the present invention provides an organic light emitting element including the compound represented by any one of the chemical formulas 1 to 5. As one example, the present invention provides an organic light-emitting element comprising: a first electrode; a second electrode opposite the first electrode; and one or more organic material layers between the first electrode and the second electrode, one or more of the organic material layers including a compound represented by any one of chemical formulas 1 to 5.
In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by any one of the chemical formulas 1 to 5. In the light emitting layer, the compound represented by any one of the chemical formulas 1 to 5 may function as a host material.
At this time, the light emitting layer may further include a known dopant, and the dopant may be included in the light emitting layer in an amount of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the compound represented by any one of the chemical formulas 1 to 5, but is not limited thereto.
The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure or a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting element of the present invention may have the following structure: in addition to the light emitting layer, a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer between the light emitting layer and the second electrode are included as the organic material layer. However, the structure of the organic light emitting element is not limited thereto, and fewer or more organic layers may be included.
In addition, the organic light emitting element of the present invention may have a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate. Further, the organic light emitting device of the present invention may have an inverted type (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate. For example, fig. 1 and 2 show the structure of an organic light emitting device according to an embodiment of the present invention.
Fig. 1 is a schematic view of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In such a structure, a compound represented by any one of the chemical formulas 1 to 5 may be included in the light emitting layer.
Fig. 2 is a schematic view of an organic light-emitting element including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In such a structure, the compound represented by any one of the chemical formulas 1 to 5 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
The organic light emitting element of the present invention may be manufactured using materials and methods known in the art, except that one or more of the organic material layers include a compound represented by any one of the chemical formulas 1 to 5. Further, when the organic light emitting element includes a plurality of organic material layers, the organic material layers may be formed using the same material or different materials.
For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal oxide having conductivity, or an alloy thereof is deposited on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation (e-beam evaporation) method to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a material that can serve as a cathode is deposited on the organic material layer. In addition to such a method, an organic light emitting element can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, when the organic light emitting element is manufactured, the compound represented by any one of the chemical formulas 1 to 5 may form the organic material layer not only by a vacuum deposition method but also by a solution coating method. The solution coating method refers to spin coating, dip coating, knife coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited thereto.
In addition to the method described, an organic light emitting element can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing 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 generally preferably a material having a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO Al or SNO 2 Combinations of metals such as Sb and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
It is generally preferable to use a material having a small work function for the cathode material so that electrons can be easily injected into the organic material 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, or alloys thereof; liF/Al or LiO 2 A multi-layer structure material such as Al, etc., but not limited thereto.
The hole injection layer is a layer for injecting holes from an electrode, and a compound having the following ability is preferably used as a hole injection material: capable of transporting holes to have a hole injection effect from the anode and an excellent hole injection effect to the light emitting layer or the light emitting material, and preventing excitons generated in the light emitting layer from being transferred to the electron injection layer or the electron injection material, and also having an excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic materials, hexanitrile-hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-and polythiophene-based conductive polymers, and the like.
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 following materials are suitably used as the hole transport material: holes can be received from the anode or the hole injection layer and transferred to the light emitting layer, and have high mobility to the holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which both conjugated portions and non-conjugated portions exist.
The light-emitting material is a material that can emit light in the visible light region by receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and a material having a favorable quantum efficiency for fluorescence or phosphorescence is preferably used as the light-emitting material. Specific examples include 8-hydroxyquinoline aluminum complex (Alq) 3 ) (ii) a Carbazole-based compounds; dimeric styrene (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
As described above, the light emitting layer may include a host material and a dopant material. The host material may further include a fused aromatic ring derivative, a heterocyclic ring-containing compound, or the like, in addition to the compound represented by any one of the chemical formulas 1 to 5. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene (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-type furan compound, a pyrimidine derivative, and the like, but is not limited thereto.
The dopant material contains an aromatic amine derivative, a styrene amine compound, a boron complex, a fluoranthene compound, a metal complex, or the like. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group and contains pyrene, anthracene, having an arylamino group,
Figure BDA0002671164800000761
And a styrylamine compound is a compound in which at least one aryl vinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group are substituted or unsubstituted. Specifically, the styrylamine compound includes, but is not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the following materials are suitably used as the electron transport material: can receive electrons from the cathode and transfer them to the light-emitting layer, and has high mobility to electrons. Specific examples include 8-hydroxyquinoline aluminum complexes; containing Alq 3 A complex compound; an organic radical compound; hydroxyflavone-metal complexes, and the like, but are not limited thereto. For the electron transport layer, any desired cathode material may be used in combination, as used in the art. In particular, examples of suitable cathode materials are conventional materials having a small work function and accompanying an aluminum or silver layer. In particular, the cathode material comprises cesium, barium, calcium, ytterbium and samarium, in each case with an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from an electrode, and a compound having the following ability is preferably used as an electron injection material: capable of transporting electrons to have an electron injection effect from a cathode and an excellent electron injection effect to a light emitting layer or a light emitting material, and preventing excitons generated in the light emitting layer from migrating to a hole injection layer, and also having an excellent thin film forming ability. Specifically, the electron injection material includes fluorenone (fluoroenone), anthraquinodimethane (anthraquinodimethane), diphenoquinone (diphenoquinone), thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like, but is not limited thereto.
The metal complex includes lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium bis (2-methyl-8-quinoline) chloride, gallium bis (2-methyl-8-quinoline) (o-cresol), aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol), and the like, but is not limited thereto.
The organic light-emitting element of the present invention may be of a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.
In addition, the compound represented by any one of the chemical formulas 1 to 5 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting element.
The present invention is described in further detail in the following examples. However, the following embodiments are only for illustrating the present invention, and the contents of the present invention are not limited to the following embodiments.
< Synthesis example >
Synthesis example 1: preparation of Compound 1-1
Compound 1-1 was prepared by the following steps 1) to 6).
Figure BDA0002671164800000781
1) Preparation of Compound 1-1-1
9H-carbazol-4-ol (9H-carbazol-4-ol) (100g, 546 mmol) was dissolved in 1L Tetrahydrofuran (THF), and N-Bromosuccinimide (N-Bromosucinimide) (97g, 546 mmol) was slowly added after the temperature was lowered to O ℃. After about 1 hour, 500mL of a saturated aqueous solution of ammonium chloride was added and stirred, then the aqueous layer was separated and the organic layer was concentrated under reduced pressure. The concentrated compound was slurried with a small amount of ethyl acetate and excess hexane and then filtered to give the compound 1-1-1 (112 g, 78% yield) as a gray solid.
2) Preparation of Compound 1-1-2
Compound 1-1-1 (50g, 190mmol) and (2-chloro-6-fluorophenyl) boronic acid (99g, 570mmol) were dispersed in tetrahydrofuran (400 ml), followed by addition of 2M aqueous potassium carbonate solution (aq.K) 2 CO 3 ) (190ml, 380mmol) and palladium tetratriphenylphosphine [ Pd (PPh) 3 ) 4 ](2.2g, 1mol%) was refluxed with stirring for 6 hours. The temperature was reduced to normal temperature and the aqueous layer was separated, the organic layer was washed once more with water, and the organic layer was separated by layering. The collected organic layer was slurried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The oily compound was combined with hexane and ethyl acetate and separated by means of a silica gel column to prepare compound 1-1-2 (48.1g, 81%) as a white solid.
3) Preparation of Compounds 1-1-3
Compound 1-1-2 (59g, 189mmol) was diluted in 400mL of N-methyl-2-pyrrolidone and potassium carbonate (52g, 190mmol) was added, followed by heating to 140 ℃. After about 1 hour, the reaction was cooled to room temperature and slowly added to 1.6L of water. The precipitated solid was filtered, dissolved in tetrahydrofuran, treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was slurried with a small amount of tetrahydrofuran and excess hexane and filtered. For purification of the filtered compound, hexane and ethyl acetate were used and separation was performed by means of a silica gel column, thereby preparing compound 1-1-3 (38.6 g, 70%).
4) Preparation of Compounds 1-1-4
Compound 1-1-3 (32g, 111mmol), bis (pinacolato) diboron (38.2g, 133mmol), potassium acetate (potassium acetate) (21.8g, 222mmol) were added to 370mL of 1, 4-dioxane, and Palladium dibenzylidene acetone Palladium (1.9 g, 3.3 mmol) and tricyclohexylphosphine (1.8 g, 6.7 mmol) under reflux stirring, and the mixture was refluxed for 12 hours. After the reaction was complete, the mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated under reduced pressure, and then ethyl acetate was added to the residue to dissolve it, followed by washing with water to separate an organic layer, followed by drying over anhydrous Magnesium sulfate (Magnesium sulfate), followed by distillation under reduced pressure and stirring with ethyl acetate and ethanol, thereby preparing compound 1-1-4 (27.6 g, 65% yield).
5) Preparation of Compounds 1-1-5
The compounds 1-1-4 (15g, 39mmol) and 2-chloro-4, 6-diphenyl-1, 3,5-triazine (10.5g, 39mmol) were dispersed in tetrahydrofuran (150 ml), followed by addition of 2M aqueous potassium carbonate (aq.K.) 2 CO 3 ) (58mL, 117mmol) and palladium tetrakis triphenylphosphine [ Pd (PPh) 3 ) 4 ](0.45g, 1mol%) and stirred under reflux for 6 hours. The temperature was reduced to normal temperature and the resulting solid was filtered off. The filtered filtrate was concentrated and re-dissolved in ethyl acetate, and then washed twice with water for separation, and then anhydrous magnesium sulfate was added for filtration and concentration. The residue after concentration was slurried with a small amount of ethyl acetate and an excess of a mixture of hexane and ethanol to prepare compound 1-1-5 (5.2 g, 27% yield) as a dark yellow color.
6) Preparation of Compound 1-1
Compound 1-1-5 (20g, 41mmol) and iodobenzene (25g, 123mmol) were dissolved in 150mL of toluene, and sodium t-butoxide (7.9g, 82mmol) was added thereto and the mixture was heated. Bis (tri-tert-butylphosphine) palladium (0.21g, 1mol%) was added thereto and the mixture was refluxed and stirred for 12 hours. After the reaction is finished, the temperature is reduced to normal temperature, and then generated solid is filtered. The yellow solid was dissolved in 700mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirring was performed, and then filtration was performed and the filtrate was distilled under reduced pressure. Purifying the concentrated compound with ethyl acetate and hexane by silica gel column to obtain dark yellow solid compoundChemical formula 1-1 (17.8g, 77%, MS: [ M + H ]] + ＝565)。
Synthesis example 2: preparation of Compounds 1-2
The reaction was carried out in the same manner as in step 6) of said compound 1-1 except for using 2-bromo-9-phenyl-9H-carbazole (13g, 41mmol) in place of iodobenzene (25g, 123mmol) to prepare a compound 1-2 (21.8g, 73%, MS: [ M + H ] -1] + ＝730)。
Figure BDA0002671164800000801
Synthesis example 3: preparation of Compound 2-1
Compound 2-1 was prepared by the following steps 1) to 7).
Figure BDA0002671164800000811
1) Preparation of Compound 2-1-1
3-chloro-2-iodophenol (3-chloro-2-iodophenol) (100g, 393mmol) and (3-bromo-2-fluorophenyl) boronic acid ((3-bromo-2-fluorophenyl) boronic acid) (86g, 393mmol) were dispersed in tetrahydrofuran (1000 ml) and 2M aqueous potassium carbonate (aq. K.) was added 2 CO 3 ) (400mL, 786 mmol) and addition of Tetratriphenylphosphine Palladium [ Pd (PPh) 3 ) 4 ](4.5g, 1mol%) was refluxed with stirring for 6 hours. The temperature is reduced to normal temperature, the water layer is separated, anhydrous magnesium sulfate is added into the organic layer for pulping, and then the organic layer is filtered and concentrated under reduced pressure. The oily compound was combined with hexane and ethyl acetate and separated by silica gel column chromatography to prepare compound 2-1-1 (90g, 76%) as a white solid.
2) Preparation of Compound 2-1-2
Using compound 2-1-1 (90g, 298mmol) and in the same manner as in the synthesis example of compound 1-1-3, an experiment was conducted to prepare compound 2-1-2 (61 g,73% yield).
3) Preparation of Compounds 2-1-3
Compound 2-1-2 (61g, 217mmol) and 2-chloroaniline (30g, 238mmol) were dissolved in 750mL of toluene, and potassium phosphate (138g, 650 mmol) was added thereto and heated. Di (tri-tert-butylphosphine) palladium (0.6 g,0.5 mol%) was added and stirred under reflux for 3 hours. After the reaction, about 500mL of toluene was removed under reflux, the temperature was lowered to normal temperature, and then the precipitated solid was filtered off. The filtered solid was dissolved in 500mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using ethyl acetate and hexane to prepare a solid compound of chemical formula 2-1-3 (48.3 g, 68% yield).
4) Preparation of Compounds 2-1-4
Compound 2-1-3 (45g, 137mmol) was dissolved in 450mL of dimethylacetamide (DMAc), followed by addition of potassium phosphate (43.6 g, 206mmol) and heating under reflux. Palladium dibenzylideneacetone 1.58g (2.74 mmol) and tricyclohexylphosphine 3.85 (13.7 mmol) were added and stirred under reflux for 6 hours. After the reaction was completed, the reaction was cooled to room temperature, and 1.8L of water was added to the reaction mixture to stir it, and then the resulting solid was filtered off. The filtered solid was completely dissolved in ethyl acetate, and then washed with water, and the separated organic layer was treated with anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The concentrated compound was purified by silica gel column chromatography using ethyl acetate and hexane to prepare a solid compound of chemical formula 2-1-4 (32.4 g,81% yield).
5) Preparation of Compounds 2-1-5
Using the compound 2-1-4 (30g, 103mmol), and in the same manner as in the synthesis example of the compound 1-1-4, an experiment was conducted to prepare the compound 2-1-5 (32.7 g, 83% yield).
6) Preparation of Compounds 2-1-6
Using the compounds 2-1-5 (30g, 78mmol) and 2- ([ 1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1,3,5-triazine (26.9g, 78mmol) and in the same manner as in the synthetic example of the compounds 1-1-5, experiments were conducted to prepare compounds 2-1-6 (38 g, yield 86%).
7) Preparation of Compound 2-1
Using the compound 2-1-6 (15g, 27mmol) and carrying out the experiment in the same manner as in the synthetic example of the compound 1-1, the compound 2-1 (12.8 g, yield 75%, MS: [ M + H ]] + ＝641)。
Synthesis example 4: preparation of Compound 3-1
Compound 3-1 was prepared by the following steps 1) to 7).
Figure BDA0002671164800000831
1) Preparation of Compound 3-1-1
An experiment was performed using the compound 3-bromo-2-iodophenol (50g, 167mmol) and (2-chloro-6-fluorophenyl) boronic acid (44g, 251mmol) and in the same manner as in the synthetic example of the compound 2-1-1 to prepare a compound 3-1-1 (41 g, yield 82%).
2) Preparation of Compound 3-1-2
Using the compound 3-1-1 (41g, 136mmol) and in the same manner as in the synthesis example of the compound 1-1-3, an experiment was conducted to prepare the compound 3-1-2 (29 g, yield 76%).
3) Preparation of Compound 3-1-3
Compounds 3-1-3 (37 g,73% yield) were prepared by conducting experiments using the compounds 3-1-2 (25g, 89mmol) and 2-chloro-4- (9-phenyl-9H-carbazol-3-yl) aniline (2-chloro-4- (9-phenyl-9H-carbazol-3-yl) aniline) (33g, 89mmol) in the same manner as in the synthetic example of the compounds 2-1-3.
4) Preparation of Compounds 3-1-4
Using compound 3-1-3 (33g, 58mmol) and carrying out the experiment in the same manner as in the synthetic example of compound 2-1-4, compound 3-1-4 (25 g, yield 81%) was prepared.
5) Preparation of Compounds 3-1-5
Using compound 3-1-4 (25g, 47mmol) and in the same manner as in the synthesis example of compound 1-1-4, an experiment was conducted to prepare compound 3-1-5 (22 g, yield 75%).
6) Preparation of Compounds 3-1-6
Using the compounds 3-1-5 (20g, 32mmol) and 2-chloro-4, 6-diphenyl-1, 3,5-triazine (8.8g, 32mmol), and carrying out the experiment in the same manner as in the synthesis example of the compound 1-1-5, the compound 3-1-6 (18.7 g, yield 80%) was prepared.
7) Preparation of Compound 3-1
Compound 3-1-6 (15g, 21mmol) was added to iodobenzene (75mL, 5vol), followed by potassium phosphate (8.7g, 41mmol) and heating. CuI (3.9g, 21mmol) was slowly added at about 60 ℃. After the reaction was completed under reflux, the reaction was cooled to room temperature and 100mL of water was added. The precipitated solid was filtered and dissolved in 1L of chloroform, and then washed twice with 2M aqueous HCl to separate an organic layer, slurried with anhydrous magnesium sulfate and acid clay, filtered and concentrated under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare Compound 3-1 (11.6 g, yield 70%, MS: [ M + H ]] + ＝806)。
Synthesis example 5: preparation of Compound 4-1
Compound 4-1 is prepared by the following steps 1) to 8).
Figure BDA0002671164800000851
1) Preparation of Compound 4-1-1
An experiment was performed using 3-bromo-4-nitrophenol (50g, 229mmol) and ([ 1,1' -biphenyl ] -4-yl) boronic acid (54g, 275mmol) in the same manner as in the synthetic example of the compound 1-1-2, thereby preparing the compound 4-1-1 (58.8 g, yield 88%).
2) Preparation of Compound 4-1-2
Using compound 4-1-1 (55g, 189mmol) and carrying out the experiment in the same manner as in the synthetic example of compound 1-1-1, compound 4-1-2 (58 g, yield 83%) was prepared.
3) Preparation of Compound 4-1-3
Using the compound 4-1-2 (50g, 135mmol) and (2-chloro-6-fluorophenyl) boronic acid (29g, 162mmol), and carrying out an experiment in the same manner as in the synthetic example of the compound 1-1-2, the compound 4-1-3 (46.0 g, yield 81%) was prepared.
4) Preparation of Compound 4-1-4
Using the compound 4-1-3 (45g, 107mmol) and in the same manner as in the synthesis example of the compound 1-1-3, an experiment was conducted to prepare the compound 4-1-4 (32.6 g, yield 76%).
5) Preparation of Compounds 4-1-5
To compound 4-1-4 (45g, 107mmol) was added triethyl phosphite (P (OEt) 3 ) (21.3 g, 128mmol) and heated with stirring. After completion of the reaction, the residual triethyl phosphite was removed by vacuum distillation, and the mixture was cooled to room temperature and stirred. Hexane and ethyl acetate were added and the resulting solid was filtered off, and the filtered solid was washed with hexane. The solid was redissolved in chloroform and washed twice with water for separation, and the organic layer was slurried with anhydrous magnesium sulfate, then filtered and concentrated under reduced pressure. The compound was recrystallized from ethanol and ethyl acetate to obtain compound 4-1-5 (30.0 g, yield 76%).
6) Preparation of Compounds 4-1-6
Using compound 4-1-5 (30g, 82mmol) and in the same manner as in the synthesis example of compound 1-1-4, an experiment was conducted to prepare compound 4-1-6 (33.0 g, 88% yield).
7) Preparation of Compounds 4-1-7
Using the compounds 4-1-6 (30g, 65mmol) and 2-chloro-4, 6-diphenyl-1, 3,5-triazine (12.0 g,68.6 mmol) and carrying out the experiment in the same manner as in the synthesis example of the compound 1-1-5, the compound 4-1-7 (28.4 g, yield 77%) was prepared.
8) Preparation of Compound 4-1
Using the compound 4-1-7 (25g, 27mmol) and conducting the experiment in the same manner as in the synthetic example of the compound 3-1, the compound 4-1 (11.0 g, yield 65%, MS: [ M + H ]] + ＝641)。
Synthesis example 6: preparation of Compound 5-1
Compound 5-1 was prepared by the following steps 1) to 7).
Figure BDA0002671164800000871
1) Preparation of Compound 5-1-1
Compound 5-1-1 (42.9 g, yield 68%) was prepared by conducting an experiment using 2-bromobenzene-1,3-diol (2-bromobenzene-1, 3-diol) (50g, 265mmol) and (2-chloro-6-fluorophenyl) boronic acid ((2-chloro-6-fluorophenyl) boronic acid) (55.3g, 317 mmol) in the same manner as in the synthesis example of Compound 1-1-2.
2) Preparation of Compound 5-1-2
Using compound 5-1-1 (41g, 172mmol) and carrying out the experiment in the same manner as in the synthetic example of compound 1-1-3, compound 5-1-2 (32.6 g,76% yield) was prepared.
3) Preparation of Compound 5-1-3
Using compound 5-1-2 (41g, 172mmol) and (2-nitrophenyl) boronic acid (34.4 g, 206mmol), and in the same manner as in the synthesis example of compound 1-1-2, an experiment was performed to prepare compound 5-1-3 (46 g, yield 81%).
4) Preparation of Compounds 5-1-4
Using compound 5-1-3 (40g, 131mmol) and carrying out the experiment in the same manner as in the synthesis example of compound 4-1-5, compound 5-1-4 (27 g, yield 76%) was prepared.
5) Preparation of Compounds 5-1-5
Compound 5-1-4 (25g, 91.5 mmol) was diluted in 200mL of acetonitrile (acetoonitrile), and Perfluorobutanesulfonyl fluoride (Perfluorobutylsulfonyl fluoride) (30.3 g,100.6 mmol) and potassium carbonate (25g, 183mmol) were dissolved in 50mL of an aqueous solution were added together. Heated to 40 ℃ for stirring and then cooled to room temperature after the reaction is complete. The aqueous layer was separated, and the organic layer was concentrated under reduced pressure. The concentrated compound was separated from hexane and ethyl acetate by silica gel column chromatography to obtain 5-1-5 (37 g,73% yield) as a white solid.
6) Preparation of Compounds 5-1-6
Compounds 5-1-6 (28.4 g, 80% yield) were prepared using compounds 5-1-5 (35g, 63mmol) and 2,4-diphenyl-6- (3- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine (2, 4-diphenyl-6- (3- (4, 5-tetramethyl-1,3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine) (28.8g, 66mmol) and conducting experiments in the same manner as the synthesis of compounds 1-1-5.
7) Preparation of Compound 5-1
An experiment was performed in the same manner as in the synthetic example of Compound 3-1, except that Compound 5-1-6 (20g, 35mmol) and 3-iodo-1,1'-biphenyl (3-iodo-1, 1' -biphenyl) (14.9g, 53mmol) were added to 100mL of toluene, to prepare Compound 5-1 (15 g, yield 75%, MS: [ M + H ]: M + H] + ＝717)。
Synthesis example 7: preparation of Compound 2-2
Compound 2-2 was prepared by the following steps 1) to 7).
Figure BDA0002671164800000891
1) Preparation of Compound 2-2-1
Compound 2-2-1 (69 g,73% yield) was prepared by conducting an experiment using 4-chloro-2-iodophenol (4-chloro-2-iodophenol) (80g, 314 mmol) and (3-bromo-2-fluorophenyl) boronic acid ((3-bromo-2-fluorophenyl) boronic acid) (72g, 330mmol) in the same manner as in the synthetic example of Compound 2-1-1.
2) Preparation of Compound 2-2-2
Using compound 2-2-1 (65g, 215mmol) and in the same manner as in the synthesis example of compound 1-1-3, an experiment was conducted to prepare compound 2-2-2 (50 g, 82% yield).
3) Preparation of Compound 2-2-3
Using compound 2-2-2 (60g, 213mmol), an experiment was carried out in the same manner as in the synthesis example of compound 2-1-3 to produce compound 2-2-3 (53 g,76% yield).
4) Preparation of Compound 2-2-4
Using compound 2-2-3 (52g, 158mmol) and carrying out the experiment in the same manner as in the synthesis example of compound 2-1-4, compound 2-2-4 (37 g, yield 80%) was prepared.
5) Preparation of Compound 2-2-5
Using compound 2-2-4 (35g, 120mmol) and in the same manner as in the synthesis example of compound 1-1-4, an experiment was conducted to prepare compound 2-2-5 (33.5 g,73% yield).
6) Preparation of Compound 2-2-6
Compounds 2-2-6 (35 g, 80% yield) were prepared by conducting experiments using compounds 2-2-5 (30g, 78mmol) and 2- ([ 1,1'-biphenyl ] -3-yl) -4-bromo-6-phenyl-1, 3,5-triazine (2- ([ 1,1' -biphenyl ] -3-yl) -4-chloro-6-phenyl-1,3, 5-triazine) (26.9g, 78mmol) in the same manner as in the synthesis example of compounds 1-1-5.
7) Preparation of Compound 2-2
Using compound 2-2-6 (17g, 30mmol) and carrying out the experiment in the same manner as in the synthetic example of compound 3-1, compound 2-2 (14.8 g,77% yield MS: [ M + H ]] + ＝641)。
Synthesis example 8: preparation of Compound 4-2
Compound 4-2 was prepared by the following steps 1) to 8).
Figure BDA0002671164800000911
1) Preparation of Compound 4-2-1
Compound 4-2-1 (71 g,81% yield) was prepared by conducting an experiment using 3-bromo-4-nitrophenol (3-bromo-4-nitrophenol) (50g, 229mmol) and (3- (9H-carbazol-9-yl) phenyl) boronic acid ((3- (9H-carbazol-9-yl) phenyl) boronic acid) (66g, 229mmol) in the same manner as in the synthetic example of Compound 1-1-2.
2) Preparation of Compound 4-2-2
Using compound 4-2-1 (70g, 184mmol), an experiment was performed in the same manner as in the synthesis example of compound 1-1-1 to prepare compound 4-2-2 (73 g, 86% yield).
3) Preparation of Compound 4-2-3
The experiment was carried out in the same manner as in the synthetic example of the compound 1-1-2 using the compound 4-2-2 (72g, 157mmol) and (4-chloro-2-fluorophenyl) boronic acid (32.8g, 188mmol) to produce the compound 4-2-3 (58 g,73% yield).
4) Preparation of Compound 4-2-4
Using compound 4-2-3 (55g, 108mmol) and in the same manner as in the synthesis example of compound 1-1-3, compound 4-2-4 (44 g, yield 83%) was prepared.
5) Preparation of Compound 4-2-5
Using compound 4-2-4 (40g, 82mmol) and in the same manner as in the synthesis example of compound 4-1-5, an experiment was conducted to prepare compound 4-2-5 (27.7 g, 74% yield).
6) Preparation of Compound 4-2-6
Using compound 4-2-5 (25g, 54mmol) and in the same manner as in the synthesis example of compound 1-1-4, an experiment was conducted to prepare compound 4-2-6 (24.6 g, 82% yield).
7) Preparation of Compound 4-2-7
Using the compounds 4-2-6 (24g, 44mmol) and 2-chloro-4, 6-diphenyl-1, 3,5-triazine (12.3g, 46mmol) and in the same manner as in the synthesis example of the compounds 1-1-5, an experiment was conducted to prepare the compounds 4-2-7 (25 g, yield 88%).
8) Preparation of Compound 4-2
Using the compound 4-2-7 (24g, 31mmol) and conducting the experiment in the same manner as in the synthetic example of the compound 3-1, the compound 4-2 (17 g, yield 75%, MS: [ M + H ]] + ＝730)。
< example >
Example 1
Will be coated with a thickness of
Figure BDA0002671164800000921
The glass substrate of the ITO (indium tin oxide) thin film of (1) was placed in distilled water in which a cleaning agent was dissolved and subjected to ultrasonic cleaning. In this case, a product of Fischer company was used as the cleaning agent, and distilled water obtained by twice filtration through a Filter (Filter) manufactured by Millipore company was used as the distilled water. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes. After the cleaning with distilled water, the mixture is ultrasonically cleaned and dried with solvents of isopropanol, acetone and methanol, and then transferred to a plasma cleaning machine. The substrate was cleaned with oxygen plasma for 5 minutes and then transferred to a vacuum deposition apparatus.
On the ITO transparent electrode thus prepared, a HI-1 compound was formed to a thickness of
Figure BDA0002671164800000931
The hole injection layer of (1).
Forming a layer of HT-1 compound on the hole injection layer by thermal vacuum deposition to a thickness of
Figure BDA0002671164800000932
Figure BDA0002671164800000933
And vacuum depositing an HT-2 compound on the HT-1 deposited film to a thickness of
Figure BDA0002671164800000934
Figure BDA0002671164800000935
The electron blocking layer of (1).
Next, compound 1-1 prepared in Synthesis example 1 was deposited on the HT-2 deposited film to a thickness of
Figure BDA0002671164800000936
And co-depositing a phosphorescent dopant GD-1 in a weight ratio of 6% to 15% to form a light emitting layer.
In the hairVacuum depositing ET-1 material on the optical layer to a thickness of
Figure BDA0002671164800000937
Then the ET-2 material and 2 weight percent of Li are co-deposited to the thickness of
Figure BDA0002671164800000938
Thereby forming an electron transport layer and an electron injection layer. Depositing aluminum on the electron injection layer to a thickness of
Figure BDA0002671164800000939
Thereby forming a cathode.
During the process, the deposition rate of the organic material is maintained
Figure BDA00026711648000009310
Aluminum deposition rate maintenance
Figure BDA00026711648000009311
And the vacuum degree is maintained at 1X 10 during deposition -7 ～5×10 -8 torr。
Examples 2 to 8
Organic light emitting elements of examples 2 to 8 were each fabricated in the same manner as in example 1, except that the phosphorescent host material and the dopant content were changed as in table 1 below when the light emitting layer was formed.
< comparative example >
Comparative examples 1 to 5
Organic light emitting elements of comparative examples 1 to 5 were respectively fabricated by the same method as the example 1, except that the phosphorescent host material and the dopant content were changed as in table 1 below when the light emitting layer was formed. At this time, the host material compounds a to C used in the comparative examples are as follows.
Figure BDA0002671164800000941
[ Compound A ]
Figure BDA0002671164800000951
[ Compound B ]
Figure BDA0002671164800000952
[ Compound C ]
Figure BDA0002671164800000953
< Experimental example >
Current was applied to the organic light emitting elements fabricated in the examples 1 to 8 and comparative examples 1 to 5, and voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 1 below. At this time, T95 represents an assumption at 20mA/cm 2 The time taken for the luminance to decrease to 95% when the initial luminance at the optical density of (1) is 100%.
[ TABLE 1]
Figure BDA0002671164800000961
As shown in table 1 above, the organic light emitting elements of examples 1 to 8 use the compound satisfying one of the structures of chemical formulas 1 to 5 as the host material of the light emitting layer, and thus satisfy both a low driving voltage of 3.3 or less and a high efficiency of 17.9% or more, and the time consumed for luminance reduction is as long as 48.2 hours or more, and excellent life performance can be achieved.
In contrast, the organic light emitting elements of comparative examples 1 and 2 using the compound a having a structure completely different from those of chemical formulas 1 to 5 as a host material had problems of high driving voltage or reduced efficiency, and the time taken for the reduction in luminance was shorter than that of the examples.
In addition, comparative examples 3 to 5 used compounds B, C, which are different from chemical formulas 1 to 5 in which functional groups were introduced at the first to third positions of indole dibenzofuran, and a functional group was introduced at the fourth position. Comparative examples 3 to 5 also have a problem of high driving voltage or reduced efficiency relative to examples. In particular, the time consumed for the luminance reduction is drastically reduced by less than 30 hours.
The invention also comprises the following technical scheme:
1. a compound represented by any one of the following chemical formulas 1 to 5:
[ chemical formula 1]
Figure BDA0002671164800000971
[ chemical formula 2]
Figure BDA0002671164800000981
[ chemical formula 3]
Figure BDA0002671164800000982
[ chemical formula 4]
Figure BDA0002671164800000983
[ chemical formula 5]
Figure BDA0002671164800000991
In the chemical formulae 1 to 5,
X 1 to X 3 Are each independently N or CR 11 And X 1 To X 3 At least one of which is N,
Y 1 is an oxygen atom or an oxygen atom,
L 1 bonding to any of the 1 to 3 positions,
L 1 is a single bond; substituted or unsubstituted C 6-60 An arylene group; or substituted or unsubstituted C containing one or more heteroatoms selected from O, N, si and S 1-60 A hetero-arylene group,
a1 is an integer of 0 to 3,
Ar 1 to Ar 3 Each independently is substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing one to three heteroatoms selected from N, O and S 1-60 (ii) a heteroaryl group, wherein,
R 1 to R 3 And R 11 Each independently is hydrogen; deuterium; a halogen; a cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; c 1-60 A haloalkyl group; substituted or unsubstituted C 1-60 An alkoxy group; substituted or unsubstituted C 1-60 A haloalkoxy group; substituted or unsubstituted C 3-60 A cycloalkyl group; substituted or unsubstituted C 2-60 An alkenyl group; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C 6-60 An aryloxy group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 1-60 A heterocyclic group,
b1 is an integer of 0 to 4,
b2 is an integer of 0 to 2,
b3 is an integer of 0 to 3.
2. The compound according to item 1, wherein,
Ar 1 is any one selected from the group:
Figure BDA0002671164800001001
Ar 2 and Ar 3 Each independently is any one selected from the group:
Figure BDA0002671164800001011
3. the compound according to item 1, which is any one compound selected from the group consisting of compounds represented by the following chemical formulae 1-1-1 to 5-1-1:
[ chemical formula 1-1-1]
Figure BDA0002671164800001021
[ chemical formula 2-1-1]
Figure BDA0002671164800001022
[ chemical formula 3-1-1]
Figure BDA0002671164800001031
[ chemical formula 4-1-1]
Figure BDA0002671164800001032
[ chemical formula 5-1-1]
Figure BDA0002671164800001041
In the chemical formulas 1-1-1 to 5-1-1,
X 1 to X 3 、R 1 、L 1 A1, b1 and Ar 1 To Ar 3 Is the same as defined in item 1.
4. The compound according to item 1, which is any one compound selected from the following compounds:
Figure BDA0002671164800001042
Figure BDA0002671164800001051
Figure BDA0002671164800001061
Figure BDA0002671164800001071
Figure BDA0002671164800001081
Figure BDA0002671164800001091
Figure BDA0002671164800001101
Figure BDA0002671164800001111
Figure BDA0002671164800001121
Figure BDA0002671164800001131
Figure BDA0002671164800001141
Figure BDA0002671164800001151
Figure BDA0002671164800001161
Figure BDA0002671164800001171
Figure BDA0002671164800001181
Figure BDA0002671164800001191
Figure BDA0002671164800001201
Figure BDA0002671164800001211
Figure BDA0002671164800001221
Figure BDA0002671164800001231
Figure BDA0002671164800001241
Figure BDA0002671164800001251
Figure BDA0002671164800001261
Figure BDA0002671164800001271
Figure BDA0002671164800001281
Figure BDA0002671164800001291
Figure BDA0002671164800001301
Figure BDA0002671164800001311
Figure BDA0002671164800001321
Figure BDA0002671164800001331
Figure BDA0002671164800001341
Figure BDA0002671164800001351
Figure BDA0002671164800001361
Figure BDA0002671164800001371
Figure BDA0002671164800001381
Figure BDA0002671164800001391
Figure BDA0002671164800001401
Figure BDA0002671164800001411
Figure BDA0002671164800001421
Figure BDA0002671164800001431
Figure BDA0002671164800001441
Figure BDA0002671164800001451
Figure BDA0002671164800001461
Figure BDA0002671164800001471
Figure BDA0002671164800001481
Figure BDA0002671164800001491
5. an organic light-emitting element comprising: a first electrode; a second electrode opposite the first electrode; and one or more organic material layers between the first electrode and the second electrode, one or more of the organic material layers comprising the compound of any one of items 1 to 4.
6. The organic light-emitting element according to item 5, wherein,
the organic material layer containing the compound is a light-emitting layer.
Description of the symbols
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light-emitting layer 8: electron transport layer

Claims (4)

1. A compound represented by any one of the following formulae:
[ chemical formula 1]
Figure FDA0003838615860000011
[ chemical formula 2]
Figure FDA0003838615860000012
[ chemical formula 3]
Figure FDA0003838615860000021
[ chemical formula 5]
Figure FDA0003838615860000022
In the chemical formula, in the presence of a catalyst,
X 1 to X 3 The content of the N is N,
Y 1 is an oxygen atom or an oxygen atom,
L 1 bonding to the 1-position, and,
L 1 is a single bond, and is a single bond,
a1 is 0 or 1, and a is,
Ar 1 is any one selected from the group:
Figure FDA0003838615860000031
Ar 2 and Ar 3 Each independently is any one selected from the group:
Figure FDA0003838615860000041
R 1 is hydrogen; c 6-20 An aryl group; carbazolyl or phenyl-substituted carbazolyl,
R 2 and R 3 Each of which is independently a hydrogen atom,
b1 is a number of 0 or 1,
b2 is an integer of 0 to 2,
b3 is an integer of 0 to 3.
2. The compound according to claim 1, which is any one compound selected from the group consisting of compounds represented by the following chemical formulae:
[ chemical formula 1-1-1]
Figure FDA0003838615860000051
[ chemical formula 2-1-1]
Figure FDA0003838615860000052
[ chemical formula 3-1-1]
Figure FDA0003838615860000061
[ chemical formula 5-1-1]
Figure FDA0003838615860000062
In the chemical formula, in the presence of a catalyst,
X 1 to X 3 、R 1 、L 1 A1, b1 and Ar 1 To Ar 3 Is as defined in claim 1.
3. The compound according to claim 1, which is any one compound selected from the group consisting of:
Figure FDA0003838615860000071
Figure FDA0003838615860000081
Figure FDA0003838615860000091
Figure FDA0003838615860000101
Figure FDA0003838615860000111
Figure FDA0003838615860000121
Figure FDA0003838615860000131
Figure FDA0003838615860000141
4. an organic light-emitting element comprising: a first electrode; a second electrode opposite the first electrode; and one or more organic material layers between the first electrode and the second electrode, the organic material layer comprising a light-emitting layer comprising the compound according to any one of claims 1 to 3.
CN202010933702.0A 2016-07-15 2017-07-14 Novel heterocyclic compound and organic light-emitting element using same Active CN112028902B (en)

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