CN109836419B9 - 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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CN109836419B9
CN109836419B9 CN201811228645.5A CN201811228645A CN109836419B9 CN 109836419 B9 CN109836419 B9 CN 109836419B9 CN 201811228645 A CN201811228645 A CN 201811228645A CN 109836419 B9 CN109836419 B9 CN 109836419B9
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CN109836419B (en
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河宰承
金渊焕
吴重锡
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LG Chem Ltd
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Abstract

The invention provides a novel heterocyclic compound and an organic light-emitting element using the same.

Description

Novel heterocyclic compound and organic light-emitting element using same
Technical Field
Cross Reference to Related Applications
The present application claims priority based on patent application No. 10-2017-.
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including 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 element using an organic light emitting phenomenon has a wide viewing angle, an excellent contrast ratio, and a fast response time, and is excellent in luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An organic light-emitting element generally has a structure including an anode and a cathode, and an organic layer located 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 composed of a multilayer structure, and the multilayer structure is composed 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 electroluminescent element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.
As for organic materials used for the organic light emitting element as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
Patent document 1: korean patent laid-open No. 10-2013-073537
Disclosure of Invention
The present invention relates to a novel heterocyclic compound and an organic light-emitting device including the same.
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure GDA0003446785570000021
In the chemical formula 1 described above,
X 1 and X 2 Each independently of the other is O or S,
L 1 each independently within the repeating unit is a direct bond, a substituted or unsubstituted C 6-60 Arylene, or a compound containing N,C substituted or unsubstituted with one or more of O and S 5-60 A hetero-arylene group,
R 1 to R 3 Each independently hydrogen, deuterium, a halogen group, cyano, tris (C) 1-60 Alkyl) silyl, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 1-60 Alkoxy, substituted or unsubstituted C 1-60 Thioalkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing more than one of N, O and S 5-60 (ii) a heteroaryl group, wherein,
R 4 each independently is a substituted or unsubstituted C containing more than one of N, O and S 5-60 Heteroaryl, C substituted by cyano 6-60 Aryl, or tri (C) 6-60 An aryl) silyl group, a silyl group,
n 1 、n 2 and m is each independently an integer of 0 to 4,
p is an integer of 0 to 4,
q is an integer of 1 to 4 and,
wherein p + q is more than or equal to 1 and less than or equal to 4,
when p and q are each 2 or more, the structures in parentheses of 2 or more are the same or different from each other.
In addition, the present invention provides an organic light emitting element including: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound of the present invention.
The compound represented by chemical formula 1 described above may be used as a material of an organic layer of an organic light emitting element in which improvement in efficiency, low driving voltage, and/or improvement in lifetime characteristics may be achieved. In particular, the above-described compound represented by chemical formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
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 illustrates an example of an organic light-emitting element composed of 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.
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
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
Figure GDA0003446785570000031
In the chemical formula 1 described above,
X 1 and X 2 Each independently of the other is O or S,
L 1 each independently within the repeating unit is a direct bond, a substituted or unsubstituted C 6-60 Arylene, or substituted or unsubstituted C containing more than one of N, O and S 5-60 A heteroarylene group.
R 1 To R 3 Each independently hydrogen, deuterium, a halogen group, cyano, tris (C) 1-60 Alkyl) silyl, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 1-60 Alkoxy, substituted or unsubstituted C 1-60 Thioalkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing more than one of N, O and S 5-60 (ii) a heteroaryl group, wherein,
R 4 each independently being comprised in N, O and SMore than one substituted or unsubstituted C 5-60 Heteroaryl, C substituted by cyano 6-60 Aryl, or tri (C) 6-60 An aryl) silyl group, a silyl group,
n 1 、n 2 and m is each independently an integer of 0 to 4,
p is an integer of 0 to 4,
q is an integer of 1 to 4 and,
wherein p + q is more than or equal to 1 and less than or equal to 4,
when p and q are each 2 or more, the structures in parentheses of 2 or more are the same or different from each other.
In the context of the present specification,
Figure GDA0003446785570000041
refers to a bond to another substituent.
The term "substituted or unsubstituted" as used herein means substituted or unsubstituted with one or more groups selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group(s) ((ii) ((iii))
Figure GDA0003446785570000042
Alkylthioxy), arylthio (A), (B), (C), (D), (E), and (E) a compound (E) and (E) a compound (E) and a compound (E) a compound (A) a compound (E) a compound (A) a compound (E) a compound (A), a compound (E) a compound (A) a compound (E) a compound (
Figure GDA0003446785570000043
Figure GDA0003446785570000044
Aryl thio), alkyl sulfoxide(s) ((s)
Figure GDA0003446785570000045
Alkyl sulfonyl), aryl sulfoxide group(s) ((s)
Figure GDA0003446785570000046
Aryl sufoxy), silyl, boryl, alkyl, cycloalkyl, alkenyl, Aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamino, arylamino, arylphosphino, or one or more of the heterocycles comprising N, O and one or more of the S atomsThe substituent (b) is substituted or unsubstituted, or substituted by a substituent in which two or more substituents among the above-mentioned substituents are bonded. For example, the "substituent in which two 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 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.
Figure GDA0003446785570000047
In the present specification, as for 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 represented by the following structural formula, but is not limited thereto.
Figure GDA0003446785570000051
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.
Figure GDA0003446785570000052
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, examples of the halogen group include fluorine, chlorine, bromine, and 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, a1, 1-dimethyl-propyl group, a, 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-butadiene, 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 cycloalkyl group has 3 to 30 carbon atoms. 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,
Figure GDA0003446785570000062
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the case where the above-mentioned fluorenyl group is substituted, it may be
Figure GDA0003446785570000061
Figure GDA0003446785570000071
And the like, but is not limited thereto.
In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent sterically closest to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Figure GDA0003446785570000072
Azolyl group,
Figure GDA0003446785570000073
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl, and benzoxazolyl
Figure GDA0003446785570000074
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Figure GDA0003446785570000075
Azolyl group,
Figure GDA0003446785570000076
Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is 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 above-mentioned aryl group. 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 examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above-mentioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, the heteroarylene group is a 2-valent group, and in addition to this, the above description about the heterocyclic group can be applied. In this 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 on the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
Preferably, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 1-1 and 1-2.
[ chemical formula 1-1]
Figure GDA0003446785570000081
[ chemical formulas 1-2]
Figure GDA0003446785570000082
In the above chemical formulas 1-1 and 1-2,
X 1 、X 2 、L 1 、R 1 、R 2 、R 3 、R 4 、n 1 、n 2 and m is as defined above.
Preferably, X 1 And X 2 May be O.
Preferably, L 1 And L 2 Each may be independently a direct bond or any one selected from the following groups.
Figure GDA0003446785570000083
More preferably, L 1 And L 2 May each independently be a direct bond,
Figure GDA0003446785570000084
Figure GDA0003446785570000085
Preferably, R 1 、R 2 And R 3 May each independently be hydrogen.
Preferably, R 4 May be represented by any one of the following chemical formulas 2 to 10.
[ chemical formula 2]
Figure GDA0003446785570000091
[ chemical formula 3]
Figure GDA0003446785570000092
[ chemical formula 4]
Figure GDA0003446785570000093
[ chemical formula 5]
Figure GDA0003446785570000094
[ chemical formula 6]
Figure GDA0003446785570000101
[ chemical formula 7]
Figure GDA0003446785570000102
[ chemical formula 8]
Figure GDA0003446785570000103
[ chemical formula 9]
Figure GDA0003446785570000104
[ chemical formula 10]
Figure GDA0003446785570000105
In the above-mentioned chemical formulas 2 to 6,
G 1 to G 30 Wherein any one of the groups contained in the respective chemical formulae is represented by the formula 1 1 The position of the bonding is the position of the bonding,
except for L of chemical formula 1 1 G remaining other than the site of bonding 1 To G 30 Each independently hydrogen, deuterium, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amide group, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 1-60 Alkoxy, substituted or unsubstituted C 6-60 Aryloxy, substituted or unsubstituted C 1-60 Alkylthio, substituted or unsubstituted C 6-60 Arylthio, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 1-60 Alkylsilyl, substituted or unsubstituted C 1-60 Alkyl boron radical, substituted or unsubstituted C 1-60 Alkylamino radical, substituted or unsubstituted C 6-60 Aryl, substituted or unsubstituted C containing more than one of N, O and S 5-60 (ii) a heteroaryl group, wherein,
in the chemical formula 7 described above,
X 1 ' to X 3 ' each independently is N or CR 1 ’，
G 31 To G 33 And R 1 ' either of which is L of chemical formula 1 1 The position of the bonding is provided with a bonding part,
in addition to L of chemical formula 1 1 G remaining outside the bonded site 31 To G 33 And R 1 ' are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstitutedC of (A) 1-60 Alkoxy, substituted or unsubstituted C 6-60 Aryloxy, substituted or unsubstituted C 1-60 Alkylthio, substituted or unsubstituted C 6-60 Arylthio, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 1-60 Alkylsilyl, substituted or unsubstituted C 1-60 Alkyl boron radical, substituted or unsubstituted C 1-60 Alkylamino radical, substituted or unsubstituted C 6-60 Aryl, substituted or unsubstituted C containing more than one of N, O and S 5-60 Heteroaryl group, wherein X 1 ' to X 3 ' are all CR 1 When R is 1 ' either of which is a nitrile group,
in the chemical formula 8 as described above,
X 4 ' to X 7 ' each independently is N or CR 2 ', wherein, X 4 ' to X 7 At least one of them is N, G 34 To G 39 And R 2 ' either of which is L of the formula 1 1 The position of the bonding is the position of the bonding,
except for L of chemical formula 1 1 G other than the site of bonding 34 To G 39 And R 2 ' are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 1-60 Alkoxy, substituted or unsubstituted C 6-60 Aryloxy, substituted or unsubstituted C 1-60 Alkylthio, substituted or unsubstituted C 6-60 Arylthio, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 1-60 Alkylsilyl, substituted or unsubstituted C 1-60 Alkyl boron radical, substituted or unsubstituted C 1-60 Alkylamino radical, substituted or unsubstituted C 6-60 Aryl, substituted or unsubstituted C containing more than one of N, O and S 5-60 (ii) a heteroaryl group, wherein,
in the chemical formula 9 above, the first and second,
Y 1 ' is O, S, NR 3 ' or CR 4 ’R 5 ’，
G 40 To G 44 And R 3 ' to R 5 ' either of which is L of the formula 1 1 The position of the bonding is provided with a bonding part,
except for L of chemical formula 1 1 G other than the site of bonding 40 To G 44 And R 3 ' to R 5 ' are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 1-60 Alkoxy, substituted or unsubstituted C 6-60 Aryloxy, substituted or unsubstituted C 1-60 Alkylthio, substituted or unsubstituted C 6-60 Arylthio, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 1-60 Alkylsilyl, substituted or unsubstituted C 1-60 Alkyl boron radical, substituted or unsubstituted C 1-60 Alkylamino radical, substituted or unsubstituted C 6-60 Aryl, substituted or unsubstituted C containing more than one of N, O and S 5-60 Heteroaryl groups, adjacent groups may be joined to each other to form a substituted or unsubstituted ring,
in the chemical formula 10 as described above,
Y 2 ' is O, S, NR 6 ' or CR 7 ’R 8 ’，
X 8 ' and X 9 ' each independently is N or CR 9 ’，
G 45 、G 46 And R 6 ' to R 9 ' either of which is L of the formula 1 1 The position of the bonding is the position of the bonding,
except for L of chemical formula 1 1 G other than the site of bonding 45 、G 46 And R 6 ' to R 9 ' are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 1-60 Alkoxy, substituted or unsubstituted C 6-60 Aryloxy radicalSubstituted or unsubstituted C 1-60 Alkylthio, substituted or unsubstituted C 6-60 Arylthio, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 1-60 Alkylsilyl, substituted or unsubstituted C 1-60 Alkyl boron radical, substituted or unsubstituted C 1-60 Alkylamino radical, substituted or unsubstituted C 6-60 Aryl, substituted or unsubstituted C containing more than one of N, O and S 5-60 A heteroaryl group.
Preferably, in the compounds represented by the above chemical formulas 2 to 6, G 1 To G 30 Wherein any one of the groups contained in the respective chemical formulae is represented by the formula 1 1 The site of bonding other than L of chemical formula 1 1 G other than the site of bonding 1 To G 30 Each independently hydrogen, substituted or unsubstituted C 6-60 Aryl group, or substituted or unsubstituted C containing 1 or more of N, O and S 5-60 A heteroaryl group.
Preferably, the compound represented by the above chemical formula 7 may be any one selected from the following chemical formulas 7-1 to 7-4.
Figure GDA0003446785570000131
In the formula, G 31 To G 33 And R 1 ' As defined above, more preferably, G 31 To G 33 And R 1 ' either of which is L of the formula 1 1 The site of bonding other than L of chemical formula 1 1 G remaining other than the site of bonding 31 To G 33 And R 1 Each independently hydrogen, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing more than one of N, O and S 5-60 A heteroaryl group.
Preferably, the compound represented by the above chemical formula 8 is any one selected from the following chemical formulas 8-1 to 8-8.
Figure GDA0003446785570000132
Figure GDA0003446785570000141
In the formula, G 34 To G 39 And R 2 ' As defined above, more preferably, G 34 To G 39 And R 2 ' either of which is L of the formula 1 1 The site of bonding other than L of chemical formula 1 1 G remaining other than the site of bonding 34 To G 39 And R 2 ' each independently is hydrogen, substituted or unsubstituted C 6-60 Aryl group, or substituted or unsubstituted C containing 1 or more of N, O and S 5-60 A heteroaryl group.
Preferably, the compound represented by the above chemical formula 9 may be any one selected from the following chemical formulas 9-1 to 9-5.
Figure GDA0003446785570000142
In the above chemical formulae 9-1 to 9-4, G 40 To G 43 And R 3 ' to R 5 ' As defined above, more preferably, G 40 To G 43 And R 3 ' to R 5 ' either of which is L of the formula 1 1 The site of bonding other than L of chemical formula 1 1 G remaining other than the site of bonding 40 To G 43 And R 3 ' to R 5 ' are each independently hydrogen, or a substituted or unsubstituted aryl group.
In the above chemical formula 9-5, G 40 To G 43 And G 1 ' to G 8 ' either of which is L of the formula 1 1 The site of bonding other than L of chemical formula 1 1 G remaining other than the site of bonding 40 To G 43 And G 1 ' to G 8 ' are each independently hydrogen, deuterium, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 1-60 Alkoxy, substituted or unsubstituted C 6-60 Aryloxy, substituted or unsubstituted C 1-60 Alkylthio, substituted or unsubstituted C 6-60 Arylthio, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 1-60 Alkylsilyl, substituted or unsubstituted C 1-60 Alkyl boron radical, substituted or unsubstituted C 1-60 Alkylamino radical, substituted or unsubstituted C 6-60 Aryl, substituted or unsubstituted C containing more than one of N, O and S 5-60 A heteroaryl group.
More preferably, G 40 To G 43 And G 1 ' to G 8 ' either of which is L of the formula 1 1 The site of bonding other than L of chemical formula 1 1 G remaining other than the site of bonding 40 To G 43 And G 1 ' to G 8 ' each independently is hydrogen, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing more than one of N, O and S 5-60 A heteroaryl group.
Preferably, the compound represented by the above chemical formula 10 may be any one selected from the following chemical formulas 10-1 to 10-9.
Figure GDA0003446785570000151
In the formula, G 45 、G 46 And R 6 ' and R 9 ' As defined above, more preferably, G 45 、G 46 And R 6 ' and R 9 ' either of which is L of the formula 1 1 The site of bonding other than L of chemical formula 1 1 G remaining other than the site of bonding 45 、G 46 And R 6 ' and R 9 ' each independently is hydrogen, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing more than one of N, O and S 5-60 A heteroaryl group.
Preferably, R 4 May be any one selected from the following groups.
Figure GDA0003446785570000161
In the above-mentioned groups, the compounds of formula,
R 5 each independently hydrogen, substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing more than one of N, O and S 5-60 A heteroaryl group.
Preferably, m may be 0 or 1.
Preferably, the compound represented by the above chemical formula 1 may be any one selected from the following groups.
Figure GDA0003446785570000171
Figure GDA0003446785570000181
Figure GDA0003446785570000191
Figure GDA0003446785570000201
Figure GDA0003446785570000211
Figure GDA0003446785570000221
Figure GDA0003446785570000231
Figure GDA0003446785570000241
Figure GDA0003446785570000251
Figure GDA0003446785570000261
Figure GDA0003446785570000271
Figure GDA0003446785570000281
Figure GDA0003446785570000291
Figure GDA0003446785570000301
Figure GDA0003446785570000311
Figure GDA0003446785570000321
Figure GDA0003446785570000331
Figure GDA0003446785570000341
Figure GDA0003446785570000351
The compound represented by the above chemical formula 1 can be produced by the following production method such as the reaction formula 1-a or the reaction formula 1-B. The above-described manufacturing method can be further embodied in the manufacturing examples described below.
[ reaction formula 1-A ]
Figure GDA0003446785570000361
[ reaction formula 1-B ]
Figure GDA0003446785570000362
In the above reaction formula 1-A or reaction formula 1-B,
X 1 、X 2 、R 4 etc. are the same as defined in chemical formula 1.
The reactants, catalysts, solvents, and the like used in the above reaction formula, and reaction conditions and the like may be appropriately changed and used according to the kind and position of the substituent of chemical formula 1 of the present invention, and specifically, may be embodied in production examples 1 to 4 described later.
In addition, the present invention provides an organic light emitting element comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include an electron transport layer or an electron injection layer including the compound represented by the chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron injection and electron transport includes the compound represented by the above chemical formula 1. In particular, the compound represented by chemical formula 1 according to the present invention is excellent in thermal stability, has a deep HOMO level of 6.0eV or more, a high triplet Energy (ET), and hole stability. In addition, when the compound represented by the above chemical formula 1 is used for an organic layer that can simultaneously perform electron injection and electron transport, an n-type dopant used in the art may be mixed and used.
In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting element according to the present invention may be an organic light emitting element having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate (normal type). In addition, the organic light emitting element according to the present invention may be an inverted type organic light emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting element according to an embodiment of the present invention is illustrated in fig. 1 and 2.
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. In this structure, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting element composed of 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 this structure, the compound represented by the above chemical formula 1 may be included in one or more layers among the above hole injection layer, hole transport layer, light emitting layer, and electron transport layer.
The organic light emitting element according to the present invention may be manufactured using materials and methods known in the art, except that one or more of the organic layers include the compound represented by the above chemical formula 1. In addition, when the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting element according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode 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 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 this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element.
In addition, the compound represented by chemical formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to this method, an organic light-emitting element may 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 SnO 2 : a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers 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 LiO 2 And a multi-layer 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: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film formation 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 polymers.
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 material is a material 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 material having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and a substance having a high quantum efficiency with respect to fluorescence or phosphorescence is preferable. As an example, there is 8-hydroxy-quinoline aluminum complex (Alq) 3 ) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Figure GDA0003446785570000392
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Figure GDA0003446785570000391
Pyrimidine derivatives, etc., but are not limited thereto.
The dopant material includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic compound having a substituted or unsubstituted arylamino groupGroup condensed ring derivatives of pyrene, anthracene, having arylamino,
Figure GDA0003446785570000393
Diindenoperene (Periflanthene) and the like, as the styrylamine compound, a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group. 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.
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 electron transport layer is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light-emitting layer. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq 3 The complex of (3), the organic radical compound, the hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, which are accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,
Figure GDA0003446785570000402
Azole,
Figure GDA0003446785570000403
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
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 element according to the present invention may be a top emission type, a bottom emission type, or a bidirectional emission type depending on the material used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting element.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same is specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
Production example 1 (Synthesis of B1 to B4)
[ reaction formula 1-1]
Figure GDA0003446785570000401
Synthesis of B1
According to the above reaction scheme 1-1, A1(30g,64.8mmol), 4-bromo-1, 2-difluorobenzene (18.76g,97.20mmol), potassium carbonate (37.61,272.2mmol) were added to DMF (300ml), and stirred under reflux. After the reaction is finished, cooling to normal temperature and filtering. After extraction with water and chloroform (chloroform) at normal temperature, the white solid was subjected to column chromatography using ethyl acetate and hexane to give the above B1(18.82g, yield 80%).
MS[M+H] + ＝364.21
Synthesis of B2
B2 was synthesized in the same manner as in the synthesis of B1, except that 1-bromo-2, 3-difluorobenzene was used instead of 4-bromo-1, 2-difluorobenzene.
MS[M+H] + ＝364.21
Synthesis of B3
B3 was synthesized in the same manner as in the synthesis of B1, except that 1, 2-dichloro-4, 5-difluorobenzene was used instead of 4-bromo-1, 2-difluorobenzene.
MS[M+H] + ＝354.20
Synthesis of B4
B4 was synthesized in the same manner as in the synthesis of B1, except that 1, 4-dichloro-2, 3-difluorobenzene was used instead of 4-bromo-1, 2-difluorobenzene.
MS[M+H] + ＝354.20
Production example 2 (Synthesis of C1 to C8)
Synthesis of C1 to C2
[ reaction formula 2-1]
Figure GDA0003446785570000421
Synthesis of C1
Compound B1(25g,68.83mmol), bis (pinacolato) diboron (20.97g,82.59mmol) and potassium acetate (23.65g,240.9mmol) were mixed under nitrogen and bis (pinacolato) was added
Figure GDA0003446785570000422
An alkane (300ml) was heated with stirring. Under reflux, bis (dibenzylideneacetone) palladium (1.19g,3 mol%) and tricyclohexylphosphine (1.13g,6 mol%) were added, heated, and stirred for 3 hours. After the reaction is finished, the temperature is reduced to normal temperature, and then filtration is carried out. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, with tetrahydrofuran and ethyl acetateRecrystallization gave the above-mentioned C1(28.23g, 83%).
MS[M+H] + ＝411.28
Synthesis of C2
C2 was produced by the same method except that B2 was used in place of B1 in the synthesis of C1.
MS[M+H] + ＝411.28
Synthesis of C3 to C5
[ reaction formula 2-2]
Figure GDA0003446785570000431
Synthesis of B1-1
According to the above reaction scheme 2-2, B1(25g,68.83mmol) and 4-chlorobenzeneboronic acid (11.30g,72.27mmol) were added to tetrahydrofuran (300ml), a 2M aqueous potassium carbonate solution (150ml) was added, tetrakis (triphenylphosphine) palladium (1.59g,2 mol%) was added, and the mixture was stirred under heating for 10 hours. The temperature was lowered to room temperature, and after the reaction was completed, the aqueous potassium carbonate solution was removed to conduct layer separation. After removal of the solvent, the white solid was recrystallized from ethyl acetate to give the above B1-1(23.1g, yield 85%).
MS[M+H] + ＝395.85
Synthesis of B1-2
B1-2 was produced by the same method except that 3-chlorobenzeneboronic acid was used instead of 4-chlorobenzeneboronic acid in the synthesis of B1-1.
MS[M+H] + ＝395.85
Synthesis of B1-3
B1-3 was produced by the same method except that 2-chlorobenzeneboronic acid was used instead of 4-chlorobenzeneboronic acid in the synthesis of B1-1.
MS[M+H] + ＝395.85
Synthesis of C3
C3 was produced by the same method except that B1-1 was used instead of B1 in the above synthesis of C1.
MS[M+H] + ＝487.37
Synthesis of C4
C4 was produced by the same method except that B1-2 was used in place of B1-1 in the above-mentioned synthesis of C3.
MS[M+H] + ＝487.37
Synthesis of C5
C5 was produced by the same method except that B1-3 was used in place of B1-1 in the above-mentioned synthesis of C3.
MS[M+H] + ＝487.37
Synthesis of C6 to C8
[ reaction formulae 2 to 3]
Figure GDA0003446785570000441
Synthesis of B2-1
B2-1 was produced by the same method except that B2 was used in place of B1 in the synthesis of B1-1 according to the reaction formula 2-3.
MS[M+H] + ＝395.85
Synthesis of B2-2
B2-2 was produced by the same method except that 3-chlorobenzeneboronic acid was used instead of 4-chlorobenzeneboronic acid in the synthesis of B2-1.
MS[M+H] + ＝395.85
Synthesis of B2-3
B2-3 was produced by the same method except that 2-chlorobenzeneboronic acid was used instead of 4-chlorobenzeneboronic acid in the synthesis of B2-1.
MS[M+H] + ＝395.85
Synthesis of C6
C6 was produced by the same method except that B2-1 was used in place of B1-1 in the above-mentioned synthesis of C3.
MS[M+H] + ＝487.37
Synthesis of C7
C7 was produced by the same method except that B2-2 was used in place of B2-1 in the above-mentioned synthesis of C6.
MS[M+H] + ＝487.37
Synthesis of C8
C8 was produced by the same method except that B2-3 was used in place of B2-1 in the above-mentioned synthesis of C6.
MS[M+H] + ＝487.37
Production example 3 (Synthesis of D1 to D2)
[ reaction formula 3-1]
Figure GDA0003446785570000461
Synthesis of D1-1
D1-1 was synthesized in the same manner as in the reaction formula 3-1 except that 2-chloro-4-phenyl-6- (3- (pyridin-2-yl) phenyl-1, 3, 5-triazine was used in place of B1 and (6-hydroxynaphthalen-2-yl) boronic acid was used in place of 4-chlorobenzeneboronic acid in the synthesis of B1-1.
MS[M+H] + ＝453.52
Synthesis of D1
Chloroform (400ml) was added to D1-1(30g,110.9mmol) and dissolved, and then perfluorobutanesulfonyl fluoride (36.85g,121.9mmol) was slowly added dropwise at room temperature, followed by stirring at room temperature for 3 hours. After extraction with water and chloroform (chloroform) at room temperature, the white solid was recrystallized from hexane to give the above-mentioned compound B2-2(56.97g, yield 93%).
MS[M+H] + ＝735-60
[ reaction formula 3-2]
Figure GDA0003446785570000462
Synthesis of D2-1
D2-1 was synthesized in the same manner as in the reaction formula 3-2, except that 2-chloro-4, 6-diphenyl-1, 3, 5-triazine was used instead of B1 and (7-hydroxy-9, 9-dimethyl-9H-fluoren-2-yl) boronic acid was used instead of 4-chlorobenzeneboronic acid in the synthesis of B1-1.
MS[M+H] + ＝442.53
Synthesis of D2
D2 was produced by the same method except that D2-1 was used in place of D1-1 in the synthesis of D1.
MS[M+H] + ＝724.61
Production example 4 (Synthesis of Compounds 1 to 21)
Synthesis of Compound 1
[ reaction formula 4-1]
Figure GDA0003446785570000471
C1(25g,68.83mmol) and 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine (11.30g,72.27mmol) were added to tetrahydrofuran (300ml), a 2M aqueous potassium carbonate solution (150ml) was added, tetrakis (triphenylphosphine) palladium (1.59g,2 mol%) was added, and the mixture was stirred under heating for 10 hours. The temperature was lowered to room temperature, and after the reaction was completed, the aqueous potassium carbonate solution was removed to conduct layer separation. After removal of the solvent, the white solid was recrystallized from ethyl acetate, thereby producing the above compound 1(23.1g, yield 85%).
MS[M+H] + ＝592.67
Synthesis of Compound 2
[ reaction formula 4-2]
Figure GDA0003446785570000481
Compound 2 was synthesized in the same manner as described above except that 2, 4-bis (1,1 '-biphenyl) 4-yl) -6-chloropyrimidine was used in place of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝667.78
Synthesis of Compound 3
[ reaction formula 4-3]
Figure GDA0003446785570000482
Compound 3 was synthesized in the same manner as in the synthesis of compound 1 above, except that C2 was used instead of C1 and 2-chloro-4-phenyl-6- (triphenylen-2-yl) -1,3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝666.75
Synthesis of Compound 4
[ reaction formula 4-4]
Figure GDA0003446785570000491
Compound 4 was synthesized by the same method except that C3 was used instead of C1 and 2- ([1,1 '-biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝668.77
Synthesis of Compound 5
[ reaction formulae 4 to 5]
Figure GDA0003446785570000492
Compound 5 was synthesized in the same manner as in the synthesis of compound 1 above, except that C3 was used instead of C1 and 2-chloro-4, 6-diphenylpyrimidine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝591.68
Synthesis of Compound 6
[ reaction formulae 4 to 6]
Figure GDA0003446785570000501
Int.1 was produced by the same synthesis method except that in the synthesis of the above compound 1, C4 was used instead of C1 and 2-chloro-4- (4-chlorophenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝627.11
Next, compound 6 was synthesized in the same manner as in the synthesis of compound 1 except that int.1 produced above was used instead of C1 and dibenzofuran-4-boronic acid was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝758.85
Synthesis of Compound 7
[ reaction formulae 4 to 7]
Figure GDA0003446785570000502
Compound 7 was synthesized in the same manner as described above except that C4 was used instead of C1 and 4-chloro-2- (naphthalen-1-yl) -6-phenylpyrimidine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝641.74
Synthesis of Compound 8
[ reaction formulae 4 to 8]
Figure GDA0003446785570000511
Int.2 was produced by the same synthesis method except that C5 was used instead of C1 and 2-chloro-4- (4-chlorophenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of the above compound 1.
MS[M+H] + ＝627.11
Int.2(15g,26.4mmol) prepared above, 9H-carbazole (15g,27.3mmol) and sodium tert-butoxide (4.56g,59.2mol) were added to xylene, and after heating and stirring, reflux was performed, and [ bis (tri-tert-butylphosphine) ] palladium (269 mg.2mmol%) was added. After the reaction was terminated by cooling to room temperature, compound 8(15.08g, 82%) was produced by recrystallization from tetrahydrofuran and ethyl acetate.
MS[M+H] + ＝757.87
Synthesis of Compound 9
[ reaction formulae 4 to 9]
Figure GDA0003446785570000512
Compound 9 was produced by the same method except that 4-chloro-6-phenyl-2- (pyridin-2-yl) pyrimidine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝592.67
Synthesis of Compound 10
[ reaction formulae 4 to 10]
Figure GDA0003446785570000521
Compound 10 was prepared by the same method except that C6 was used instead of C1 and 4- ([1,1 '-biphenyl ] -3-yl) -2-chloro-6-phenylpyrimidine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝667.78
Synthesis of Compound 11
[ reaction formulae 4 to 11]
Figure GDA0003446785570000522
Compound 11 was synthesized in the same manner as in the synthesis of compound 1 above, except that C6 was used instead of C1 and 2-chloro-4- (9, 9-dimethyl-9H-fluoren-2-yl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝708.83
Synthesis of Compound 12
[ reaction formulae 4 to 12]
Figure GDA0003446785570000531
Compound 12 was synthesized in the same manner as described above except that C7 was used instead of C1 and 2-chloro-4- (phenanthren-2-yl) -6-phenylpyrimidine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝691.81
Synthesis of Compound 13
[ reaction formulae 4 to 13]
Figure GDA0003446785570000532
Compound 13 was synthesized by the same method as the above-described synthesis of compound 1, except that C7 was used instead of C1 and 2- ([1,1 '-biphenyl ] -3-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝668.77
Synthesis of Compound 14
[ reaction formulae 4 to 14]
Figure GDA0003446785570000541
Compound 14 was synthesized in the same manner as in the synthesis of compound 1 above, except that C8 was used instead of C1 and 2- ([1,1 '-biphenyl ] -2-yl) -4-chloro-6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝667.78
Synthesis of Compound 15
[ reaction formulae 4 to 15]
Figure GDA0003446785570000542
Int.3 was produced by the same synthesis method except that in the synthesis of the above compound 1, C8 was used instead of C1 and 2-chloro-4- (3-chlorophenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝627.11
Compound 15 was synthesized by the same method except that int.3 produced above was used instead of C1 and (3-cyanophenyl) boronic acid was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝693.78
Synthesis of Compound 16
[ reaction formulae 4 to 16]
Figure GDA0003446785570000551
Compound 16 was synthesized by the same method except that D1 was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1 above.
MS[M+H] + ＝719.82
Synthesis of Compound 17
[ reaction formulae 4 to 17]
Figure GDA0003446785570000552
Compound 17 was synthesized by the same method as the above synthesis of compound 1, except that C7 was used instead of C1 and 2- ([1,1 '-biphenyl ] -4-yl) -4- (3-chlorophenyl) -6-phenyl-1, 3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝744.87
Synthesis of Compound 18
[ reaction formulae 4 to 18]
Figure GDA0003446785570000561
Compound 18 was synthesized by the same method as the above-described synthesis of compound 1, except that B4 was used instead of C1 and 2, 4-diphenyl-6- (3- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝900.03
Synthesis of Compound 19
[ reaction formulae 4 to 19]
Figure GDA0003446785570000562
Compound 19 was synthesized by the same method as the above-described compound 1, except that B3 was used instead of C1 and 2, 4-diphenyl-6- (4- (4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) phenyl) -1,3, 5-triazine was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝900.03
Synthesis of Compound 20
[ reaction formulae 4 to 20]
Figure GDA0003446785570000571
Compound 20 was synthesized by the same method except that C2 was used instead of C1 and D2 was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine in the synthesis of compound 1.
MS[M+H] + ＝708.83
Synthesis of Compound 21
[ reaction formulae 4 to 21]
Figure GDA0003446785570000572
Compound 21 was synthesized by the same method as the above synthesis of compound 1, except that C2 was used instead of C1 and 4- ([1,1 '-biphenyl ] -4-yl) -2-chloroquinazoline was used instead of 2- ([1,1' -biphenyl ] -4-yl) -4-chloro-6-phenyl-1, 3, 5-triazine.
MS[M+H] + ＝565.64
Example 1
Will be provided with
Figure GDA0003446785570000581
The glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. As the detergent, a product of fisher corporation (Fischer Co.) was used, and as the distilled water, distilled water obtained by filtering 2 times with a Filter (Filter) manufactured by Millipore Co was used. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating 2 times with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.
On the ITO transparent electrode thus prepared
Figure GDA0003446785570000582
The thickness of (1) was measured by thermal vacuum evaporation of hexanitrile hexaazatriphenylene (HI-1) to form a hole injection layer. HT1 as a hole transporting substance was vacuum-evaporated on the hole injection layer
Figure GDA0003446785570000583
Then, the above-mentioned hole transport layer is covered with
Figure GDA0003446785570000584
The film thickness of (1) was vacuum-evaporated with HT2 to form a hole-regulating layer. As a compound light-emitting layer, a host material BH1 and a dopant material BD1 compound (25:1) are mixed
Figure GDA0003446785570000585
Vacuum evaporation to the thickness of (1). Then, ETM1 compound is formed
Figure GDA0003446785570000586
As the electron adjusting layer, the compound 1 synthesized in production example 4 and LiQ (1:1,
Figure GDA0003446785570000587
) The electron transport layer is formed in sequence by co-evaporation. Sequentially depositing an electron transport layer on the substrate
Figure GDA0003446785570000588
Lithium fluoride (LiF), Mg and Ag (10:1,
Figure GDA0003446785570000589
) Performing evaporation
Figure GDA00034467855700005810
The cathode was formed of aluminum in a thickness to manufacture an organic light emitting element.
In the above process, the evaporation speed of the organic material is maintained
Figure GDA00034467855700005811
Maintenance of lithium fluoride
Figure GDA00034467855700005812
The deposition rate of aluminum is maintained at 3 to 3
Figure GDA00034467855700005813
The deposition rate of (3).
Figure GDA0003446785570000591
Examples 2 to 11 and comparative examples 1 to 4
In example 1, an organic light-emitting element was produced by the same method as in example 1 except that the compound shown in table 1 was used instead of the compound 1 as the electron transport layer and the ratio of the electron transport layer to LiQ was the ratio shown in table 1.
Test example 1: evaluation of organic light-emitting element Performance
Current (20 mA/cm) was applied to the organic light-emitting elements fabricated in examples 2 to 11 and comparative examples 1 to 4 described above 2 ) In the above case, the voltage, efficiency, luminance, color coordinates and lifetime were measured, and the results are shown in table 2 below.
[ TABLE 1]
Figure GDA0003446785570000601
Example 12
Will be provided with
Figure GDA0003446785570000602
The glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. As the detergent, a product of fisher corporation (Fischer Co.) was used, and as the distilled water, distilled water obtained by filtering 2 times with a Filter (Filter) manufactured by Millipore Co was used. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating 2 times with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.
On the ITO transparent electrode thus prepared
Figure GDA0003446785570000603
The thickness of (1) was measured by thermal vacuum evaporation of hexanitrile hexaazatriphenylene (HI-1) to form a hole injection layer. HT1 as a hole transporting substance was vacuum-evaporated on the hole injection layer
Figure GDA0003446785570000611
Then, the above-mentioned hole transport layer is covered with
Figure GDA0003446785570000612
The film thickness of (1) was vacuum-evaporated with HT2 to form a hole-regulating layer. As a compound light-emitting layer, a host material BH1 and a dopant material BD1 compound (25:1) are mixed
Figure GDA0003446785570000613
Vacuum evaporation to the thickness of (1). Then, compound 1 synthesized in production example 4 was added
Figure GDA0003446785570000614
Formed as an electronically regulated layer, was electrically modulated with ETM2 and LiQ (1:1,
Figure GDA0003446785570000615
) The electron transport layer is formed in sequence by co-evaporation. Sequentially depositing an electron transport layer on the substrate
Figure GDA0003446785570000616
Lithium fluoride (LiF), Mg and Ag (10:1,
Figure GDA0003446785570000617
) Performing evaporation
Figure GDA0003446785570000618
The cathode was formed of aluminum in a thickness to manufacture an organic light emitting element.
In the above process, the evaporation speed of the organic material is maintained
Figure GDA0003446785570000619
Maintenance of lithium fluoride
Figure GDA00034467855700006110
The deposition rate of aluminum is maintained at 3 to 3
Figure GDA00034467855700006111
The deposition rate of (3).
Examples 13 to 29 and comparative examples 5 to 8
In example 12, an organic light-emitting element was produced by the same method except that the compound shown in table 2 was used instead of ETM1 as the electron control layer and the ratio of the electron transport layer to LiQ was the ratio shown in table 2.
Test example 2: evaluation of organic light-emitting element Performance
Current (20 mA/cm) was applied to the organic light-emitting elements fabricated in examples 13 to 29 and comparative examples 5 to 8 described above 2 ) In the above case, the voltage, efficiency, luminance, color coordinates and lifetime were measured, and the results are shown in table 2 below.
[ TABLE 2]
Figure GDA0003446785570000621
As shown in the above tables 1 and 2, the compound derivatives of the chemical formula according to the present invention may play electron transporting and electron modulating roles in organic electronic devices represented by organic light emitting devices, and the devices according to the present invention show excellent characteristics in terms of efficiency, driving voltage, stability, lifetime characteristics.
In the case of the compound used as a comparative example, it was confirmed that the life characteristics were significantly reduced as compared with the compound of the present invention.

Claims (6)

1. A compound represented by the following chemical formula 1:
chemical formula 1
Figure FDA0003584337490000011
In the chemical formula 1, the metal oxide is represented by,
X 1 and X 2 Is a compound of the formula (I) O,
L 1 each independently within the repeating unit is a direct bond or is selected from any one of the following groups:
Figure FDA0003584337490000012
R 1 to R 3 Each of which is independently hydrogen, is,
R 4 each independently is any one selected from the group represented by the following chemical formulae 2 to 7:
chemical formula 2
Figure FDA0003584337490000021
Chemical formula 3
Figure FDA0003584337490000022
Chemical formula 4
Figure FDA0003584337490000023
Chemical formula 5
Figure FDA0003584337490000024
Chemical formula 6
Figure FDA0003584337490000031
Chemical formula 7
Figure FDA0003584337490000032
In the chemical formulae 2 to 6,
G 1 to G 30 Wherein any one of the groups contained in the respective chemical formulae is represented by the formula 1 1 The position of the bonding is the position of the bonding,
except for L of chemical formula 1 1 G remaining other than the site of bonding 1 To G 30 Each independently hydrogen, unsubstituted C 6-60 Aryl radicals containing either N, O and SMore than one unsubstituted C 5-60 (ii) a heteroaryl group, wherein,
in the chemical formula 7, the first and second organic solvents,
X 1 ' to X 3 ' each independently is N or CR 1 ’，
G 31 To G 33 And R 1 ' either of which is L of chemical formula 1 1 The position of the bonding is the position of the bonding,
except for L of chemical formula 1 1 G remaining other than the bonding site 31 To G 33 And R 1 ' independently of one another are hydrogen, unsubstituted or via a nitrile group or C 2-60 Heterocyclyl-substituted C 6-60 Aryl, or unsubstituted C containing more than one of N, O and S 5-60 (ii) a heteroaryl group, wherein,
n 1 and n 2 Each of which is independently a number 4,
m is 0 or 1, and m is,
p is an integer of 0 to 4,
q is an integer of 1 to 4,
wherein p + q is more than or equal to 1 and less than or equal to 4,
when p and q are each 2 or more, the structures in parentheses of 2 or more are the same or different from each other.
2. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of compounds represented by the following chemical formulae 1-1 and 1-2:
chemical formula 1-1
Figure FDA0003584337490000041
Chemical formula 1-2
Figure FDA0003584337490000042
In the chemical formulas 1-1 and 1-2,
X 1 、X 2 、L 1 、R 1 、R 2 、R 3 、R 4 、n 1 、n 2 and m is as defined in claim 1.
3. The compound of claim 1, wherein R 4 Is any one selected from the following groups:
Figure FDA0003584337490000043
in the above-mentioned groups, the compounds of formula,
R 5 each independently hydrogen, unsubstituted C 6-60 Aryl, or unsubstituted C containing more than one of N, O and S 5-60 A heteroaryl group.
4. A compound selected from any one of the following compounds:
Figure FDA0003584337490000051
Figure FDA0003584337490000061
Figure FDA0003584337490000071
Figure FDA0003584337490000081
Figure FDA0003584337490000091
Figure FDA0003584337490000101
Figure FDA0003584337490000111
Figure FDA0003584337490000121
Figure FDA0003584337490000131
Figure FDA0003584337490000141
Figure FDA0003584337490000151
Figure FDA0003584337490000161
Figure FDA0003584337490000171
Figure FDA0003584337490000181
Figure FDA0003584337490000191
Figure FDA0003584337490000201
Figure FDA0003584337490000211
Figure FDA0003584337490000221
Figure FDA0003584337490000231
5. an organic light-emitting element comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 4.
6. The organic light-emitting element according to claim 5, wherein the organic layer containing the compound is an electron injection layer, an electron transport layer, or a layer in which electron injection and electron transport are performed simultaneously.
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