KR20160059413A - Multicyclic compound including nitrogen and organoluminescent device using the same - Google Patents
Multicyclic compound including nitrogen and organoluminescent device using the same Download PDFInfo
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Abstract
Description
The present application claims the benefit of Korean Patent Application No. 10-2014-0160811 filed on November 18, 2014, filed with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.
The present invention relates to an organic electroluminescent device material and an organic electroluminescent device including the same.
An electroluminescent device is one type of self-luminous display device, and has advantages of wide viewing angle, excellent contrast, and high response speed.
The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.
The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used. In addition, as the material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.
The present invention provides a nitrogen-containing polycyclic compound and an organic electroluminescent device including the same.
One embodiment of the present disclosure provides compounds represented by Formula 1:
[Chemical Formula 1]
In Formula 1,
Cy1 to Cy3 are the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group,
X is N or CR,
L1 is a direct bond; A substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 6 to 30 carbon atoms,
Z and Z 'are the same or different from each other,
At least one of Z and Z 'is represented by any one of the following formulas (2) to (6)
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
n and m are each independently 0 or 1,
at least one of n and m is 1,
p 1 and q 1 are each independently an integer of 1 to 4,
p 2 to p 4 each independently represent an integer of 1 to 3, q 2 to q 4 each independently represent an integer of 1 to 4,
p 5 and q 5 are each independently an integer of 1 to 5, p + q is 5 or less,
When p 1 to p 5 are each independently an integer of 2 or more, a plurality of Ar 1 s are the same as or different from each other,
q 1 to q 5 are each independently an integer of 2 or more, a plurality of Ar 2 s are the same as or different from each other,
R and Ar1 to Ar3 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to adjacent groups to form a ring.
Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1, to provide.
The compound according to the present invention can be used as an organic layer material of an organic electroluminescent device. The compound can act as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like in an organic electroluminescent device. A compound according to one embodiment may be used as a light emitting host material of an organic electroluminescent device, such as a phosphorescent host material, particularly, a red phosphorescent host material. The compound according to another embodiment may be used as an electron transporting layer material of an organic electroluminescence device.
FIGS. 1 to 3 illustrate a stacking order of electrodes and organic layers of an organic electroluminescent device according to embodiments of the present invention.
Hereinafter, the present invention will be described in more detail.
The present invention provides a compound represented by the above formula (1).
In the present specification,
As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An arylamine group; Or a substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
In the present specification, the carbon number of the carbonyl group is not particularly limited,
40 < / RTI > Specifically, it may be a compound having the following structure,
.
In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.
In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
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 isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.
In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. 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 cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.
In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
In the present specification, the number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.
In the present specification, the aryl group is not particularly limited, but preferably has 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 phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
When the fluorenyl group is substituted,
In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N and S as a heteroatom. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.
In the present specification, the aryl groups in the aryloxy group, arylthioxy group, arylsulfoxy group, arylphosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group and arylamine group are exemplified by the above- same.
In the present specification, the alkyl group in the alkylthio group, the alkylsulfoxy group, the aralkyl group, the aralkylamine group, the alkylaryl group and the alkylamine group is the same as the above-mentioned alkyl group.
In the present specification, the heteroaryl group in the heteroaryl group and the heteroarylamine group can be applied to the description of the above-mentioned heterocyclic group.
In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
In the present specification, the term " forming a ring by bonding to adjacent groups " means forming a ring by bonding to adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; Or a substituted or unsubstituted aromatic heterocycle.
As used herein, the term "adjacent group" means a group in which the substituent is substituted with an atom directly bonded to the atom to which the substituted atom is substituted, a substituent having the closest stereostructure to the substituent, It can mean. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent groups ".
In the present specification, an aliphatic hydrocarbon ring means a ring which is a non-aromatic ring and consists only of carbon and hydrogen atoms.
In the present specification, examples of the aromatic hydrocarbon ring include a phenyl group, a naphthyl group, and an anthracenyl group, but are not limited thereto.
As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more of the N, O, or S atoms as heteroatoms.
As used herein, an aromatic heterocycle refers to an aromatic ring containing one or more of N, O, or S atoms as heteroatoms.
In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.
In one embodiment of the present specification, Cy1 is a substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic heterocyclic group containing at least one N atom.
In one embodiment of the present specification, Cy1 is substituted or unsubstituted benzene.
In one embodiment of the present specification, Cy1 represents a halogen group; An alkyl group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heterocyclic group, or a substituted or unsubstituted benzene group selected from the group consisting of a substituted or unsubstituted C2-C30 heterocyclic group.
In one embodiment of the present specification, Cy1 represents a halogen group; An alkyl group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted pyridine group, or a substituted or unsubstituted benzene group.
In one embodiment of the present disclosure, the Cy1 is benzene.
In one embodiment of the present specification, Cy2 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
In one embodiment of the present disclosure, Cy2 is substituted or unsubstituted naphthalene; Or substituted or unsubstituted benzene.
In one embodiment of the present specification, Cy2 is substituted or unsubstituted benzene.
In one embodiment of the present disclosure, the Cy2 is benzene.
In one embodiment of the present specification, Cy2 is substituted or unsubstituted naphthalene.
In one embodiment of the present disclosure, Cy2 is naphthalene.
In one embodiment of the present specification, Cy3 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
In one embodiment of the present disclosure, Cy3 is substituted or unsubstituted naphthalene; Or substituted or unsubstituted benzene.
In one embodiment of the present specification, Cy3 is substituted or unsubstituted benzene.
In one embodiment of the present disclosure, the Cy3 is benzene.
In one embodiment of the present specification, Cy3 is substituted or unsubstituted naphthalene.
In one embodiment of the present disclosure, Cy3 is naphthalene.
In one embodiment of the present specification, Cy2 and Cy3 are substituted or unsubstituted aromatic hydrocarbon rings having 6 to 30 carbon atoms.
In another embodiment, the Cy2 and Cy3 are substituted or unsubstituted benzenes.
In one embodiment of the present disclosure, Cy2 is substituted or unsubstituted naphthalene, and Cy3 is substituted or unsubstituted benzene.
In one embodiment of the present disclosure, Cy2 is substituted or unsubstituted benzene, and Cy3 is substituted or unsubstituted naphthalene.
In one embodiment of the present disclosure, m is zero.
In one embodiment of the present disclosure, n is one.
In one embodiment of the present disclosure, m is 0 and n is 1.
In one embodiment of the present disclosure, X is CR.
In one embodiment of the present disclosure, X is CR and R is hydrogen or a substituted or unsubstituted aryl group.
In one embodiment of the present disclosure, X is CR and R is hydrogen.
In one embodiment of the present disclosure, X is CR and R is substituted or unsubstituted benzene.
In one embodiment of the present disclosure, X is N.
In one embodiment of the present disclosure, L1 is a direct bond; Or a substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms.
In one embodiment of the present disclosure, L1 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent naphthalene group.
In another embodiment, L1 is a direct bond.
In one embodiment of the present specification, L1 is a substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms.
In one embodiment of the present specification, L 1 is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted divalent naphthalene group.
In one embodiment of the present specification, at least one of Z and Z 'is represented by Formula 2 or Formula 3 above.
In another embodiment, at least one of Z and Z 'is represented by any one of formulas (4) to (6).
In one embodiment of the present specification, at least one of Z and Z 'is represented by the above formula (7).
In one embodiment of the present disclosure, at least one of Z and Z 'is a substituted or unsubstituted carbazole group; Or a substituted or unsubstituted benzocarbazole group.
In one embodiment of the present invention, at least one of Z and Z 'is a carbazolyl group substituted or unsubstituted with a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a benzocarbazole group substituted or unsubstituted with a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In the present specification, the (benzo) carbazole group means a carbazole group or a benzocarbazole group.
In one embodiment of the present invention, at least one of Z and Z 'is a substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted fluorenyl group Substituted or unsubstituted (benzo) carbazole group.
In one embodiment of the present invention, at least one of Z and Z 'is a (benzo) carbazolyl group substituted or unsubstituted with a naphthyl group or deuterium.
In another embodiment, Z and Z 'are substituted or unsubstituted carbazole groups.
In one embodiment of the present invention, Z and Z 'are carbazol groups substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, Z and Z 'are carbazol groups substituted or unsubstituted with substituted or unsubstituted phenyl groups.
In one embodiment of the present invention, the formula (6) is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted phenanthrene group.
In one embodiment of the present invention, at least one of Z and Z 'is represented by any one of formulas (2), (6) and (7) to (18).
(7)
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
(11)
[Chemical Formula 12]
[Chemical Formula 13]
[Chemical Formula 14]
[Chemical Formula 15]
[Chemical Formula 16]
[Chemical Formula 17]
[Chemical Formula 18]
In claims 7 to 19, p 2 to p 4 , q 2 to q 4, and Ar 1 to Ar 3 are the same as described above.
In one embodiment of the present specification, p 2 is 1 or 2.
In one embodiment of the present disclosure, p 2 is one.
In one embodiment of the present specification, q 2 is an integer of 1 to 3.
In one embodiment of the present disclosure, q 2 is 1 or 2.
In one embodiment of the present disclosure, q < 2 >
In another embodiment, p 3 is 1 or 2.
In one embodiment of the present disclosure, p 3 is one.
In one embodiment of the present specification, q 3 is an integer of 1 to 3.
In one embodiment of the present disclosure, q 3 is 1 or 2.
In one embodiment of the present disclosure, q < 3 >
In one embodiment of the present specification, p 4 is 1 or 2.
In another embodiment, p 4 is 1.
In one embodiment of the present specification, q 4 is an integer of 1 to 3.
In one embodiment of the present disclosure, q 4 is 1 or 2.
In one embodiment of the present disclosure, q < 4 >
In the above Chemical Formulas 7 to 18,
p, q and Ar1 to Ar3 are the same as defined in formula (1).
In one embodiment of the present specification, m is 0, and the formula (1) is represented by any one of the following formulas (1-1) to (1-7).
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
[Formula 1-4]
[Formula 1-5]
[Chemical Formula 1-6]
[Chemical Formula 1-7]
In the above formulas 1-1 to 1-7,
Cy1, X, L1, Ar1 to Ar3, p 2 and q 2 are the same as defined in formula (1),
R1 and R2 are the same as or different from each other, the same as the definition of Ar1 to Ar3,
a is an integer of 1 to 3,
When a is an integer of 2 or more, a plurality of R1's are the same as or different from each other,
b is an integer of 1 to 4,
When b is an integer of 2 or more, a plurality of R2s are the same or different from each other.
In one embodiment of the present invention, the formula (1) is represented by the following formula (1-8) or (1-9).
[Chemical Formula 1-8]
[Chemical Formula 1-9]
In the above formulas 1-8 and 1-9,
Cy1, X, L1, Ar1 to Ar3, p 2 and q 2 are the same as defined in formula (1),
R1 and R3 are the same as or different from each other and are the same as defined for Ar1 to Ar3,
a is an integer of 1 to 4,
When a is an integer of 2 or more, a plurality of R1's are the same as or different from each other,
c is an integer of 1 to 5,
When c is an integer of 2 or more, the plurality of R 3 are the same or different from each other.
In one embodiment of the present invention, the compound represented by Formula 1 may be represented by any of the following structures.
In one embodiment of the present invention, the compound represented by Formula 1 may be represented by any of the following structures.
In one embodiment of the present invention, the compound represented by Formula 1 may be represented by any of the following structures.
The compounds according to the present specification can be easily prepared by known methods. For example, when L1 in the general formula (1-1) is a substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms, [ J. Med . Chem . 1973 , 16 , 528], [Paper Archiv der Pharmazie 1936 , 274 , 8] and [Thesis Chem . Rev. 1995 , 95 , 2457], the following reaction scheme 1 can be prepared.
[Reaction Scheme 1]
Further, when L1 is a direct bond in Formula 1-1, [papers Rec. Trav . chim . 1961, 80, 149], [ J. Med . Chem . 1973 , 16 , 528] and [ Chem . Rev. 1995 , 95 , 2457], the following reaction scheme 2 can be prepared.
[Reaction Scheme 2]
In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1 do.
The organic material layer of the organic electroluminescent device may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic layers.
In one embodiment of the present invention, the organic material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, (1).
In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound of the general formula (1).
In one embodiment of the present disclosure, the compound of Formula 1 is a phosphorescent host material or a fluorescent host material.
In one embodiment of the present invention, the compound of Formula 1 is a red phosphorescent host material.
In one embodiment of the present invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound of the above formula (1).
In one embodiment of the present invention, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound of the above formula (1).
In another embodiment, the organic material layer includes a light emitting layer and an electron transporting layer, and the electron transporting layer includes the compound of the above formula (1).
In another embodiment, the organic electroluminescent device may be a normal type organic electroluminescent device in which an anode, at least one organic material layer, and a cathode are sequentially stacked on a substrate.
In another embodiment, the organic electroluminescent device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.
FIGS. 1 to 3 illustrate the stacking process of electrodes and organic layers of an organic electroluminescent device according to embodiments of the present invention. However, it is not intended that the scope of the present invention be limited by these drawings, and the structure of the organic electroluminescent device known in the art can be applied to the present invention.
1, an organic electroluminescent device in which an
FIG. 3 illustrates the case where the organic material layer is a multilayer. 3 includes a
The organic electroluminescent device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, i.e., the compound of the above formula (1).
When the organic electroluminescent device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
The organic electroluminescent device of the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer contains the compound of Formula 1, that is, the compound represented by Formula 1. [
For example, the organic electroluminescent 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, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic electroluminescent device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
In addition to such a method, an organic electroluminescent device can also be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.
In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.
In another embodiment, the first electrode is a cathode and the second electrode is a cathode.
As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro 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 is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.
The electron transporting material is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
In one embodiment of the present invention, the compound of Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic electroluminescent device.
The preparation of the compound represented by Formula 1 and the organic electroluminescent device including the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.
<Production Example>
For the synthesis of the compound represented by the above formula (1), the compounds of the following formulas (a) to (c) can be used as a starting material.
PREPARATION EXAMPLE 1 Preparation of the starting material represented by the formula a
2-oxo-1,2-dihydroquinoline-4-carboxylic acid (3.78 g, 20 mmol), thionyl chloride (1.60 mL, 22 mmol) And 20 mL of benzene were stirred in a nitrogen atmosphere. Dimethylformamide (0.6 ml) was slowly added dropwise, and the mixture was stirred at the same temperature for 2 hours. Then, the solvent was removed under reduced pressure and vacuum dried to prepare a white solid (4.11 g).
The white solid (4.11 g) was stirred in benzene and nitrogen atmosphere at 0 ° C. After adding 28% ammonia water (1.3 mL) and water (10 mL), the temperature was raised to room temperature and further stirred for 12 hours. The product was extracted with chloroform, and water was removed with anhydrous magnesium sulfate (MgSO4). The solvent was removed under reduced pressure to prepare a white solid (3.53 g) having an amide functional group.
The above white solid (3.53 g), phosphorus oxychloride (POCl 3 , 20 Ml), phosphorus pentachloride (PCl 5 , 7.81 g, 37.5 mmol) and 1,4- dioxane (10 mL) Was refluxed under a nitrogen atmosphere. After refluxing for 8 hours, the reaction mixture was cooled to 0 ° C and the reaction was terminated with aqueous sodium carbonate solution. The product was extracted with chloroform, and water was removed with anhydrous magnesium sulfate (MgSO 4 ), and the solvent was removed under reduced pressure. The resulting solid was filtered, washed with ethanol, and dried in vacuo to give 2.08 g (59% yield) of formula (a).
MS: [M + H] < + > = 189
PREPARATION EXAMPLE 2 Preparation of the starting material represented by formula (b)
2-oxo-1,2-dihydroquinazoline-4-carboxylic acid (3.80 g, 20 mmol), thionyl chloride (1.60 mL, 22 mmol ) And 20 mL of benzene were stirred in a nitrogen atmosphere. Dimethylformamide (0.6 mL) was slowly added dropwise, and the mixture was stirred at the same temperature for 2 hours. Then, the solvent was removed under reduced pressure and vacuum dried to prepare a white solid (4.11 g).
The white solid (4.11 g) was stirred in benzene and nitrogen atmosphere at 0 ° C. After adding 28% ammonia water (1.3 mL) and water (10 mL), the temperature was raised to room temperature and further stirred for 12 hours. The product was extracted with chloroform, and water was removed with anhydrous magnesium sulfate (MgSO 4 ). The solvent was removed under reduced pressure to give a white solid (3.53 g) having an amide functional group.
The above white solid (3.53 g), phosphorus oxychloride (POCl 3 , 20 Ml), phosphorus pentachloride (PCl 5 , 7.81 g, 37.5 mmol) and 1,4- dioxane (10 mL) Was refluxed under a nitrogen atmosphere. After refluxing for 8 hours, the reaction mixture was cooled to 0 ° C and the reaction was terminated with aqueous sodium carbonate solution. The product was extracted with chloroform, the water was removed with anhydrous magnesium sulfate (MgSO4), and the solvent was removed under reduced pressure. The resulting solid was filtered, washed with ethanol and dried in vacuo to give 2.19 g (58% yield) of formula b.
MS: [M + H] < + > = 190
PREPARATION EXAMPLE 3 Preparation of the starting material represented by formula (c)
4-chloro-3-phenylquinolin-2 (1H) -one (5.11 g, 20 mmol) was dissolved in dimethylformaldehyde (DMF 1 L) sodium para-toluene sulfinate was added (sodium p -toluenesulfinate, 5.34 g, 30 mmol) for 20 h followed by stirring at 120 o C. After lowering the temperature to room temperature, water was added to obtain a solid, which was filtered and dried in vacuo to give 5.25 g (70% yield) of a yellow solid.
5.25 g of the above yellow solid was dissolved in dimethylformaldehyde (
The yellow solid (2.06 g), phosphorous oxychloride (POCl 3 , 10 mL) and 1,4-dioxane (10 mL) were refluxed under nitrogen atmosphere. After refluxing for 8 hours, the reaction mixture was cooled to 0 ° C and the reaction was terminated with aqueous sodium carbonate solution. The product was extracted with chloroform, the water was removed with anhydrous magnesium sulfate (MgSO4), and the solvent was removed under reduced pressure. The resulting solid was filtered, washed with ethanol and dried in vacuo to give 2.04 g (92% yield) of the formula c.
MS: [M + H] < + > = 275
Preparation Example 4 Preparation of Compound A
Compound A-1 Compound A-2 Compound A
Preparation of Compound A-1
16.7 g (0.1 mol) of carbazole was dissolved in tetrahydrofuran (THF, 500 mL), and the mixture was stirred at 0 ° C for 10 minutes. N-Bromosuccinimide (NBS, 18.68 g, 0.105 mol) was added, stirred at room temperature for 12 hours, and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and the residue was subjected to silica gel column chromatography to obtain 22.4 g (91%) of Compound A-1.
Preparation of Compound A-2
9-phenyl-9H-carbazol-2-yl) boronic acid, 31.3 g, 109 mmol), Pd ( PPh 3 ) 4 (5.25 g, 4.5 mmol), 60 mL of 2 MK 2 CO 3 aqueous solution, 300 mL of toluene and 90 mL of ethanol were placed and stirred at reflux for 12 hours. Washed with distilled water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and the residue was subjected to silica gel column chromatography to obtain 29.7 g (72.8 mmol, 80%) of Compound A-2.
Preparation of Compound A
60% sodium hydride (1.16 g, 29 mmol) and 40 mL of dehydrated dimethylformamide were added to a nitrogen-purged flask and stirred. 100 mL of dimethylformamide was added to and dissolved in Compound A-2 (11.84 g, 29 mmol) obtained above, and then dropped into the flask for 15 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. 100 mL of dimethylformamide was added to and dissolved in the starting material represented by Formula b (5.69 g, 30 mmol), and the mixture was then added dropwise to the flask for 10 minutes. After completion of the addition, stirring was continued for 4 hours. Then, 0.6 L of water was added, and crystals precipitated were collected by filtration. The crystals collected by filtration were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 14.60 g (26 mmol, 87% yield) of Compound A.
MS: [M + H] < + > = 562 PREPARATION EXAMPLE 5 Preparation of Compound B
Formula B-1 Compound B-2 Compound B
Preparation of Formula B-1
20.4 g (0.1 mol) of 7H-benzo [c] carbazole was dissolved in tetrahydrofuran (THF, 500 mL), and the mixture was stirred at 0 ° C for 10 minutes. N-Bromosuccinimide (NBS, 18.68 g, 0.105 mol) was added, stirred at room temperature for 12 hours, and then extracted with distilled water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and the residue was subjected to silica gel column chromatography to obtain 25.4 g (86%) of compound B-1.
Preparation of Formula B-2
Phenyl-7H-benzo [c] carbazole-9-boronic acid, 32.3 g, 96 mmol (9 mmol) ), Pd (PPh 3) 4 (5.25 g, 4.5 mmol), 2 MK 2 CO 3 aqueous solution 80 mL, 400 mL toluene, 160 mL of ethanol were placed and stirred under reflux for 12 hours. Washed with distilled water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and silica gel column chromatography gave 33.4 g (65.6 mmol, 82%) of compound B-2
Preparation of Compound B
60% sodium hydride (1.20 g, 30 mmol) and 40 mL of dehydrated dimethylformamide were added to a nitrogen-purged flask and stirred. 100 mL of dimethylformamide was added to and dissolved in the starting material (5.12 g, 27 mmol) represented by the formula b, and then added dropwise in the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. Then, 100 mL of dimethylformamide was added to and dissolved in 14.24 g (28 mmol) of the compound B-2 obtained above, and then dropped into the flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Then, 0.6 L of water was added, and crystals precipitated were collected by filtration. The filtered crystals were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 14.55 g (22 mmol, 81% yield) of compound B.
MS: [M + H] < + > = 662
Preparation Example 6 Preparation of Compound C
Formula B-1 Compound C-1 Compound C
Preparation of Formula C-1
The compound B-1 17.7 synthesized in Preparation Example 5 g (60 mmol), dibenzo thiophene-2-boronic acid (Dibenzothiophene-2-boronic acid, 17.1 g, 75 mmol), Pd (PPh 3) 4 (3.46 g , 3 mmol), 60 mL of 2 MK 2 CO 3 aqueous solution, 300 mL of toluene and 120 mL of ethanol, and the mixture was refluxed and stirred for 12 hours. Washed with distilled water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and silica gel column chromatography gave Compound C-1 19.4 g (65.6 mmol, 81%) was obtained
Preparation of Compound C
60% sodium hydride (0.80 g, 20 mmol) and 30 mL of dehydrated dimethylformamide were added to a nitrogen-purged flask and stirred. 60 mL of dimethylformamide was added to the starting material represented by the formula (b) (3.22 g, 17 mmol), and the mixture was then added dropwise to the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. Then, 60 mL of dimethylformamide was added to and dissolved in the compound C-1 (7.20 g, 18 mmol) obtained above, and then dropped into the flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Thereafter, 0.4 L of water was added, and the precipitated crystals were collected by filtration. The filtered crystals were dispersed in ethanol, stirred for one day, filtered, and vacuum dried to obtain 7.54 g (12 mmol, 70% yield) of Compound C. MS: [M + H] < + > = 540
PREPARATION EXAMPLE 7 Preparation of Compound (D)
Preparation of Formula D-1
3-Chloro-9H-carbazole (20.1 g, 100 mmol) and 43.5 g (184 mmol) of 1-bromo-4-iodobenzene were dissolved in 500 mL of toluene. Then, 9.2 g (48 mmol) mL (96 mmol) and tripotassium phosphate (9.1 g, 288 mmol) were added and refluxed for 24 hours. After the mixture was cooled to room temperature, the reaction was terminated with hydrochloric acid diluted with water, extracted with chloroform, and washed with distilled water. The obtained organic layer was dried over anhydrous sodium sulfate (MgSO 4 ) and the solvent was removed. The silica gel column chromatography was conducted to obtain 19.6 g (55.0 mmol, 55%) of the compound D-1.
Preparation of Formula D-2
The compound D-1 (18.2 g, 51 mmol) was dissolved in 300 mL of THF, cooled to -78 ° C, and 25.0 mL of n-BuLi (2.5 M in hexane) was added slowly. After stirring at -78 ° C for 2 hours, 8.5 mL of B (OMe) 3 was added, and the mixture was slowly stirred and stirred. An aqueous solution of ammonium chloride was added thereto to terminate the reaction. Extracted with chloroform, and washed with distilled water. The obtained organic layer was dried over anhydrous sodium sulfate (MgSO 4 ) and the solvent was removed. The residue was subjected to silica gel column chromatography to obtain 11.1 g (55.0 mmol, 68%) of compound D-2.
Preparation of Formula D-3
Compound b 2.84 g (15 mmol), compound D-2 4.50 g (14 mmol ) of tetrahydrofuran (THF) 100 mL and then a solution in water, 40 mL, Pd (PPh 3) 4 0.86 g (0.75 mmol) and potassium carbonate (K 2 CO 3) 4.14 g was added. The mixture was stirred at reflux for 8 hours, then cooled to room temperature and the reaction was terminated with 20 mL of aqueous ammonium chloride solution. The mixture was extracted with chloroform and washed with distilled water. The obtained organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and the residue was subjected to silica gel column chromatography to obtain 5.0 g (11.7 mmol, 78%) of the compound D-3.
Preparation of Formula D-4
The compound Compound D-3 (4.30 g, 10 mmol), bis (pinacolato) diboron (3.04 g, 12 mmol) and potassium acetate (2.94 g, 30 mmol) were mixed in a nitrogen atmosphere and added to 40 mL of dioxane And heated with stirring. Bis (dibenzylidine acetone) palladium (0.457 g, 0.5 mmol) and tricyclohexylphosphine (0.28 g, 1.0 mmol) were added under reflux and heated and stirred for 10 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was extracted with distilled water and chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the residue was recrystallized from ethanol to obtain 4.12 g (7.9 mmol, 79%) of the compound D-4.
Preparation of compound D
The compound represented by the above compound D-4 (5.22 g, 10.0 mmol) and the compound represented by the formula A-1 (3.86 g, 12.0 mmol) synthesized in Preparation Example 4 were completely dissolved in 50 mL of tetrahydrofuran in a nitrogen atmosphere , 25 Ml of a 2M potassium carbonate aqueous solution was added, and tetrakistriphenylphosphinopalladium (1.10 g, 1.0 mmol) was added thereto, followed by heating and stirring for 2 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was suspended. The filtered white solid was washed once with tetrahydrofuran and ethanol, respectively, to give 5.50 g (8 mmol, 80%) of the compound D.
MS: [M + H] < + > = 688 PREPARATION EXAMPLE 8 Preparation of Compound E
E-1 Compound E
Preparation of Formula E-1
200 mL of tetrahydrofuran was added to 14.8 g (50 mmol) of the compound B-1 synthesized in Preparation Example 5 and dibenzo [b, d] furan-4-ylboronic acid (12.7 g, 60 mmol) 3 ) 4 (2.89 g, 2.5 mmol) and 2 mL of MK 2 CO 3 aqueous solution were added, and the mixture was refluxed and stirred for 12 hours. The mixture was cooled to room temperature and extracted with chloroform and distilled water. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and the residue was subjected to silica gel column chromatography to obtain 16.1 g (42 mmol, 84%) of compound E-1.
Preparation of Compound E
Compound E-1 11.5 g (30 mmol ) of the compound represented by formula c 5.3 g (20 mmol), CuI 7.6 g (40 mmol), Cs 2 CO 3 (19.5 g, 60 mmol), trans-1,2- 0.716 mL (6 mmol) of aminocyclohexane and 130 mL of 1,2-dichlorobenzene were added, and the mixture was refluxed and stirred at 180 ° C for 12 hours. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), and the solvent was removed. Silica gel column chromatography to obtain Compound 12 (12.4 g, 20.4 mmol, 68%).
MS: [M + H] < + > = 612
PREPARATION EXAMPLE 9 Preparation of Compound F
F-1 Compound F
Preparation of Formula F-1
200 mL of tetrahydrofuran was added to 14.8 g (50 mmol) of the compound B-1 synthesized in Preparation Example 5 and (9,9-dimethyl-9H-fluoren-2-yl) boronic acid (14.3 g, After the addition, Pd (PPh 3 ) 4 (2.89 g, 2.5 mmol) and 100 mL of 2 MK 2 CO 3 aqueous solution were added and stirred at reflux for 12 hours. The mixture was cooled to room temperature and extracted with chloroform and distilled water. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and the residue was subjected to silica gel column chromatography to obtain 16.0 g (39 mmol, 78%) of Compound F-1.
Preparation of Compound F
F-1 12.3 g (30 mmol ) of the compound represented by the formula b 5.3 g (20 mmol), CuI 7.6 g (40 mmol), Cs 2 CO 3 (19.5 g, 60 mmol), trans-1,2-diamino Cyclohexane (0.716 mL, 6 mmol) and 1,2-dichlorobenzene (130 mL) were added and the mixture was refluxed and stirred at 180 ° C for 12 hours. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), and the solvent was removed. The residue was purified by silica gel column chromatography to obtain Compound F (10.9 g, 19.5%) as a colorless oil. mmol, 65%).
MS: [M + H] < + > = 562.
PREPARATION EXAMPLE 10 Preparation of Compound G
G-1 Compound G
Preparation of Formula G-1
60% sodium hydride (0.80 g, 20 mmol) and 30 mL of dehydrated dimethylformamide were added to a nitrogen-purged flask and stirred. To 60 mL of 3-bromo-7H-benzo [c] carbazole (5.0 g, 17 mmol) was added dimethylformamide, and the mixture was then added dropwise to the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. 60 mL of dimethylformamide was added to and dissolved in the compound represented by formula (b) (3.41 g, 18 mmol), followed by dropwise addition in the flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Thereafter, 0.4 L of water was added, and the precipitated crystals were collected by filtration. The crystals collected by filtration were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 5.95 g (13.2 mmol, 78% yield) of Compound G-1.
Preparation of Compound G
0.21 g (0.94 mmol) of palladium (II) acetate, xylene (20 mL) and 0.76 g (3.76 mmol) of tri-tert-butylphosphine were added and the mixture was stirred at 60 ° C for 30 minutes. The G-1 heating the solution in a nitrogen stream 60 o C (8.1 g, 18 mmol), 7H- benzo [c] carbazole (3.9 g, 18 mmol) and tert- butoxy sodium 7.7 g (80 mmol) Of xylene (180 mL). Thereafter, the temperature was raised to 130 ° C and the mixture was heated and stirred for 5 hours. After cooling to room temperature, 200 mL of water was added. The organic layer was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate (MgSO 4 ). The solvent was removed, and silica gel column chromatography was conducted to obtain 8.0 g (13.7 mmol, 76%) of Compound G.
MS: [M + H] < + > = 586
PREPARATION EXAMPLE 11 Preparation of Compound H
H-1 compound H
Preparation of Formula H-1
300 mL of tetrahydrofuran was added to 16.1 g (50 mmol) of 3-bromo-6-phenyl-9H-carbazole and 9.1 g of phenyl-3-carbazoleboronic acid pinacolate (22.1 g, (PPh 3) 4 (2.89 g , 2.5 mmol), 2 MK 2 CO 3 aqueous solution into 100 mL and the mixture was stirred under reflux for 12 hours. The mixture was cooled to room temperature and extracted with chloroform and distilled water. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), the solvent was removed, and the residue was subjected to silica gel column chromatography to obtain 17.4 g (39 mmol, 72%) of compound H-1.
Preparation of Compound H
60% sodium hydride (0.80 g, 20 mmol) and 30 mL of dehydrated dimethylformamide were added to a nitrogen-purged flask and stirred. 80 mL of dimethylformamide was added to and dissolved in the H-1 (8.2 g, 17 mmol), followed by dropwise addition into the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. 60 mL of dimethylformamide was added to and dissolved in the compound represented by formula (b) (3.41 g, 18 mmol), followed by dropwise addition in the flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Thereafter, 0.4 L of water was added, and the precipitated crystals were collected by filtration. The crystals collected by filtration were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 6.72 g (10.5 mmol, 62% yield) of Compound H.
MS: [M + H] < + > = 638
PREPARATION EXAMPLE 12 Preparation of Compound (I)
Compound A-2 Compound I
Preparation of Compound (I)
Compound A-2 12.3 g (30 mmol ) of the compound represented by formula c 5.3 g (20 mmol), CuI 7.6 g (40 mmol), Cs 2 CO 3 (19.5 g, 60 mmol), trans-1,2- 0.716 mL (6 mmol) of aminocyclohexane and 130 mL of 1,2-dichlorobenzene were added, and the mixture was refluxed and stirred at 180 ° C for 12 hours. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), and the solvent was removed. The residue was purified by silica gel column chromatography to obtain Compound I (9.2 g, 14.4 mmol, 48%).
MS: [M + H] < + > = 637
PREPARATION EXAMPLE 13 Preparation of Compound J
Compound A-2 Compound J
Preparation of Compound J
Compound A-2 12.3 g (30 mmol ) of the compound represented by the formula a 3.8 g (20 mmol), CuI 7.6 g (40 mmol), Cs 2 CO 3 (19.5 g, 60 mmol), trans-1,2- 0.716 mL (6 mmol) of aminocyclohexane and 130 mL of 1,2-dichlorobenzene were added, and the mixture was refluxed and stirred at 180 ° C for 12 hours. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), and the solvent was removed. The residue was subjected to silica gel column chromatography to obtain 7.1 g of compound J (12.6 g, mmol, 42%).
MS: [M + H] < + > = 561
PREPARATION EXAMPLE 14 Preparation of Compound K
Preparation of compound K
Compound B-2 15.3 g (30 mmol ) of the compound represented by the formula a 3.8 g (20 mmol), CuI 7.6 g (40 mmol), Cs 2 CO 3 (19.5 g, 60 mmol), trans-1,2- 0.716 mL (6 mmol) of aminocyclohexane and 130 mL of 1,2-dichlorobenzene were added, and the mixture was refluxed and stirred at 180 ° C for 12 hours. The organic layer was dried over anhydrous sodium sulfate (MgSO 4 ), and the solvent was removed. Silica gel column chromatography was conducted to obtain 11.1 g (16.8 mmol, 56%).
MS: [M + H] < + > = 661
PREPARATION EXAMPLE 15 Preparation of Compound L
Compound F-1 Compound L
Preparation of Compound L
60% sodium hydride (0.80 g, 20 mmol) and 30 mL of dehydrated dimethylformamide were added to a nitrogen-purged flask and stirred. To the above F-1 (7.0 g, 17 mmol) was added 80 mL of dimethylformamide to dissolve, and then dropped into the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. 60 mL of dimethylformamide was added to and dissolved in the compound represented by formula (b) (3.41 g, 18 mmol), followed by dropwise addition in the flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Thereafter, 0.4 L of water was added, and the precipitated crystals were collected by filtration. The crystals collected by filtration were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 5.74 g (10.2 mmol, 60% yield) of Compound H.
MS: [M + H] < + > = 563
PREPARATION EXAMPLE 16 Preparation of Compound (M)
Preparation of Compound (M)
Compound D-4 Compound M
The compound represented by the above compound D-4 (5.22 g, 10.0 mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (3.27 g, 12.0 mmol) was dissolved in tetrahydrofuran And then 25 mL of 2M potassium carbonate aqueous solution was added thereto. Tetraquistriphenylphosphinopalladium (1.10 g, 1.0 mmol) was added thereto, followed by heating and stirring for 2 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was suspended. The filtered white solid was washed once with tetrahydrofuran and ethanol, respectively, to obtain 3.53 g (6 mmol, 60%) of the compound M.
MS: [M + H] < + > = 589
PREPARATION EXAMPLE 17 Preparation of Compound N
Preparation of Formula N-1
60% sodium hydride (0.80 g, 20 mmol) and 30 mL of dehydrated dimethylformamide were added to a nitrogen-purged flask and stirred. To 60 mL of 3-bromo-7H-benzo [c] carbazole (5.0 g, 17 mmol) was added dimethylformamide, and the mixture was then added dropwise to the flask for 10 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes. 60 mL of dimethylformamide was added to and dissolved in the compound represented by formula (a) (3.40 g, 18 mmol), followed by dropwise addition in a copper flask for 30 minutes. After completion of the dropwise addition, stirring was continued for 4 hours. Thereafter, 0.4 L of water was added, and the precipitated crystals were collected by filtration. The crystals collected by filtration were dispersed in ethanol, stirred for one day, filtered and vacuum dried to obtain 5.02 g (11.2 mmol, 66% yield) of the compound N-1.
Preparation of Compound N
0.21 g (0.94 mmol) of palladium (II) acetate, xylene (20 mL) and 0.76 g (3.76 mmol) of tri-tert-butylphosphine were added and the mixture was stirred at 60 ° C for 30 minutes. This solution was heated under a stream of nitrogen 60 o C N-1 (8.1 g, 18 mmol), 7H- benzo [c] carbazole (3.9 g, 18 mmol) and tert- butoxy sodium 7.7 g (80 mmol) Of xylene (180 mL). Thereafter, the temperature was raised to 130 ° C and the mixture was heated and stirred for 5 hours. After cooling to room temperature, 200 mL of water was added. The organic layer was extracted with chloroform, and the organic layer was dried over anhydrous sodium sulfate (MgSO 4 ). The solvent was removed, and silica gel column chromatography was conducted to obtain 7.4 g of compound N (12.6 mmol, 70%).
MS: [M + H] < + > = 585
≪ Experimental Examples 1 to 14 >
Compounds synthesized in the Production Examples were subjected to high purity sublimation purification by a conventionally known method, and red organic light emitting devices were prepared as follows.
A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 Å was immersed in distilled water containing a dispersing agent and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.
After the substrate was mounted in a vacuum chamber, the substrate was adjusted to have a pressure of 1 × 10 -6 torr. Then, an organic material was injected onto the ITO using DNTPD (700 Å), NPB (300 Å) (10 wt%) was co-evaporated (300 Å) as a dopant and Alq3 (350 Å), LiF (5 Å) and Al (1,000 Å) Respectively. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, the deposition rate of LiF was 0.2 Å / sec, and the deposition rate of aluminum was 3 to 7 Å / sec.
≪ Comparative Example 1 &
The organic electroluminescent device for the comparative example was the same as the organic electroluminescent device except that CBP which is widely used as a general phosphorescent host material instead of the compound prepared by the preparation example of the present specification was used as the host of the light emitting layer in the device structures of Experimental Examples 1 to 14 A light emitting device was fabricated.
≪ Comparative Example 2 &
The organic light emitting device for the comparative example was fabricated in the same manner as the organic light emitting device except that the following compound O-1 was used in place of the compound prepared by the preparation example of this specification as a host of the light emitting layer in the device structures of Experimental Examples 1 to 14 Respectively.
≪ Comparative Example 3 &
The organic light emitting device for the comparative example was fabricated in the same manner as the organic light emitting device except that the following compound O-2 was used in place of the compound prepared by the preparation example of this specification as a host of the light emitting layer in the device structures of Experimental Examples 1 to 15 Respectively.
The driving voltage, the current efficiency, the power efficiency, and the lifetime of the organic luminescent devices manufactured by Experimental Examples 1 to 14 and Comparative Examples 1 to 3 were measured and the results are shown in Table 1 below.
(V)
(cd / A)
(lm / w)
(T95 @ 10mA)
Referring to Table 1, Compounds A to N, which are experimental examples in which the compound of the present invention was used as a host material for a light emitting layer, showed a decrease in driving voltage and improved current efficiency as compared with Comparative Examples 1 to 3, .
100: substrate 200: anode
300: organic layer 301: hole injection layer
302: Hole transport layer 303: Light emitting layer
304: electron transport layer 305: electron injection layer
400: cathode
Claims (19)
[Chemical Formula 1]
In Formula 1,
Cy1 to Cy3 are the same or different and are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group,
X is N or CR,
L1 is a direct bond; A substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 30 carbon atoms; Or a substituted or unsubstituted divalent heterocyclic group having 6 to 30 carbon atoms,
Z and Z 'are the same or different from each other,
At least one of Z and Z 'is represented by any one of the following formulas (2) to (6)
(2)
(3)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
n and m are each independently 0 or 1,
at least one of n and m is 1,
p 1 and q 1 are each independently an integer of 1 to 4,
p 2 to p 4 each independently represent an integer of 1 to 3, q 2 to q 4 each independently represent an integer of 1 to 4,
p 5 and q 5 are each independently an integer of 1 to 5, p + q is 5 or less,
When p 1 to p 5 are each independently an integer of 2 or more, a plurality of Ar 1 s are the same as or different from each other,
q 1 to q 5 are each independently an integer of 2 or more, a plurality of Ar 2 s are the same as or different from each other,
R and Ar1 to Ar3 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; A substituted or unsubstituted aralkenyl group; A substituted or unsubstituted alkylaryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be bonded to adjacent groups to form a ring.
(7)
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
(11)
[Chemical Formula 12]
[Chemical Formula 13]
[Chemical Formula 14]
[Chemical Formula 15]
[Chemical Formula 16]
[Chemical Formula 17]
[Chemical Formula 18]
In the above Chemical Formulas 7 to 18,
p 2 to p 4 , q 2 to q 4 and Ar 1 to Ar 3 are the same as defined in claim 1.
A compound represented by any one of the following formulas 1-1 to 1-7:
[Formula 1-1]
[Formula 1-2]
[Formula 1-3]
[Formula 1-4]
[Formula 1-5]
[Chemical Formula 1-6]
[Chemical Formula 1-7]
In the above formulas 1-1 to 1-7,
Cy1, X, L1, Ar1 to Ar3, p 2 and q 2 are the same as defined in formula (1),
R1 and R2 are the same as or different from each other, the same as the definition of Ar1 to Ar3,
a is an integer of 1 to 3,
When a is an integer of 2 or more, a plurality of R1's are the same as or different from each other,
b is an integer of 1 to 4,
When b is an integer of 2 or more, a plurality of R2s are the same or different from each other.
[Chemical Formula 1-8]
[Chemical Formula 1-9]
In the above formulas 1-8 and 1-9,
Cy1, X, L1, Ar1 to Ar3, p 2 and q 2 are the same as defined in formula (1),
R1 and R3 are the same as or different from each other and are the same as defined for Ar1 to Ar3,
a is an integer of 1 to 4,
When a is an integer of 2 or more, a plurality of R1's are the same as or different from each other,
c is an integer of 1 to 5,
When c is an integer of 2 or more, the plurality of R 3 are the same or different from each other.
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| US14/941,194 US9698358B2 (en) | 2014-11-18 | 2015-11-13 | Nitrogen-containing polycyclic compound and organic electroluminescent device using the same |
| CN201510788877.6A CN105601621B (en) | 2014-11-18 | 2015-11-17 | Nitrogenous polycyclic compound and the organic electroluminescence device for using it |
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| KR20140160811 | 2014-11-18 | ||
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018182300A1 (en) * | 2017-03-27 | 2018-10-04 | 주식회사 엘지화학 | Heterocyclic compound and organic light-emitting device comprising same |
| WO2020004844A1 (en) * | 2018-06-28 | 2020-01-02 | 에스케이머티리얼즈 주식회사 | Compound, organic electroluminescent element, and display device |
| CN112979549A (en) * | 2021-02-22 | 2021-06-18 | 上海天马有机发光显示技术有限公司 | Organic compound, electroluminescent material, OLED device and display panel |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018182300A1 (en) * | 2017-03-27 | 2018-10-04 | 주식회사 엘지화학 | Heterocyclic compound and organic light-emitting device comprising same |
| US11192884B2 (en) | 2017-03-27 | 2021-12-07 | Lg Chem, Ltd. | Heterocyclic compound and organic light-emitting device comprising same |
| WO2020004844A1 (en) * | 2018-06-28 | 2020-01-02 | 에스케이머티리얼즈 주식회사 | Compound, organic electroluminescent element, and display device |
| KR20200015495A (en) * | 2018-06-28 | 2020-02-12 | 에스케이머티리얼즈 주식회사 | Compounds, Organic Electroluminescent Devices and Display Devices |
| CN112979549A (en) * | 2021-02-22 | 2021-06-18 | 上海天马有机发光显示技术有限公司 | Organic compound, electroluminescent material, OLED device and display panel |
| CN112979549B (en) * | 2021-02-22 | 2023-08-29 | 武汉天马微电子有限公司 | Organic compound, electroluminescent material, OLED device and display panel |
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