Compound and organic light-emitting element comprising same
阅读说明：本技术 化合物和包含其的有机发光元件 (Compound and organic light-emitting element comprising same ) 是由 徐尚德 洪性佶 金性昭 于 2018-07-27 设计创作，主要内容包括：本说明书提供了化学式1的化合物和包含其的有机发光器件。(The present specification provides a compound of chemical formula 1 and an organic light emitting device including the same.)
1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein, in chemical formula 1,
ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms;
ar2 and Ar4 are identical to each other, and Ar3 and Ar5 are identical to each other;
ar2 to Ar5 are each a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;
r1 and R2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; and
n and m are each an integer of 0 to 5, and when n is 2 or more, R1 are the same as or different from each other, and when m is 2 or more, R2 are the same as or different from each other.
2. The compound of claim 1, wherein Ar1 is unsubstituted or alkyl or silyl substituted phenyl, unsubstituted or alkyl or silyl substituted biphenyl, unsubstituted or alkyl or silyl substituted naphthyl, unsubstituted or alkyl or silyl substituted phenanthryl, unsubstituted or alkyl or silyl substituted dibenzofuranyl, or unsubstituted or alkyl or silyl substituted dibenzothiophenyl.
3. The compound of claim 1, wherein each of Ar2 to Ar5 is phenyl unsubstituted or substituted with a substituent selected from the group consisting of alkyl, silyl, and aryl; biphenyl unsubstituted or substituted with a substituent selected from the group consisting of alkyl, silyl and aryl; or a dibenzofuranyl group which is unsubstituted or substituted by a substituent selected from the group consisting of an alkyl group, a silyl group and an aryl group.
4. The compound of claim 1, wherein R1 and R2 are hydrogen.
5. The compound of claim 1, wherein the compound of formula 1 is selected from the following structural formulae:
6. an organic light emitting device comprising:
a first electrode;
a second electrode disposed opposite the first electrode; and
one or more layers of organic material disposed between the first electrode and the second electrode,
wherein one or more layers of the organic material layer comprise a compound according to any one of claims 1 to 5.
7. The organic light-emitting device according to claim 6, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains the compound.
8. The organic light-emitting device according to claim 6, wherein the organic material layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer contains the compound.
9. The organic light-emitting device according to claim 6, wherein the organic material layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer contains the compound.
10. The organic light-emitting device according to claim 6, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer contains the compound as a blue dopant.
11. The organic light-emitting device according to claim 10, wherein the light-emitting layer further comprises an anthracene-containing compound as a host.
12. The organic light emitting device of claim 11, wherein the host is represented by the following chemical formula a:
[ chemical formula A ]
In the chemical formula A, the compound represented by the formula A,
ar11 and Ar12 are the same or different from each other and are each independently substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group; and
g1 to G8 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.
13. The organic light emitting device according to claim 12, wherein the chemical formula a is represented by the following chemical formula a-1:
[ chemical formula A-1]
In the chemical formula A-1, the compound,
ar11 is substituted or unsubstituted aryl;
x is O or S;
g10 is hydrogen; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or two or more adjacent G10 are bonded to each other to form a ring; and
p is an integer of 0 to 4, and when p is 2 or more, G10 are the same as or different from each other.
14. The organic light emitting device of claim 12, wherein formula a is selected from the following structural formulae:
15. the organic light emitting device of claim 13, wherein formula a-1 is selected from the following structural formulae:
Technical Field
The present specification relates to compounds and organic light emitting devices comprising the same.
The specification claims priority and benefit of korean patent application No. 10-2017-.
Background
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 are combined and paired in the organic thin film, and light is emitted when the electrons and holes disappear. The organic thin film may be formed as a single layer or a plurality of layers as necessary.
The material of the organic thin film may have a light-emitting function as needed. For example, as a material of the organic thin film, a compound which can form a light-emitting layer by itself may be used alone, or a compound which can function as a host or a dopant of the light-emitting layer based on a host-dopant may be used. In addition to these, a compound which can exert the functions of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like can be used as a material of the organic thin film.
There is a continuing need to develop organic thin film materials to improve the performance, lifetime, or efficiency of organic light emitting devices.
Disclosure of Invention
Technical problem
The present description relates to providing compounds and organic light emitting devices comprising the same.
Technical scheme
One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In chemical formula 1, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms,
ar2 and Ar4 are identical to each other, and Ar3 and Ar5 are identical to each other,
ar2 to Ar5 are each a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,
r1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and
n and m are each an integer of 0 to 5, and when n is 2 or more, R1 are the same as or different from each other, and when m is 2 or more, R2 are the same as or different from each other.
Another embodiment of the present application provides an organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the above compound.
Advantageous effects
By being used in an organic light emitting device, the compound according to one embodiment of the present application can reduce a driving voltage of the organic light emitting device through thermal stability of the compound, improve light efficiency and improve device lifetime characteristics.
Drawings
Fig. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are successively laminated.
Fig. 2 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are successively laminated.
[ reference numerals ]
1: substrate
2: anode
3: luminescent layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: electron transport layer
Detailed Description
Hereinafter, the present specification will be described in more detail.
One embodiment of the present specification provides a compound represented by chemical formula 1.
The compound of chemical formula 1 adopts a structure in which an arylamine group, a heteroarylamine group or an arylheteroarylamine group is linked to a dibenzo [ c, g ] carbazolyl group (as a basic skeleton) in the N-meta direction.
The N-meta direction is a direction in which conjugation continues, and when the amine group is attached to a portion other than the N-meta direction, the conjugation length increases, thereby emitting light having a longer wavelength than blue. In addition, the carbazolyl or benzocarbazolyl structure has a low electron density, thereby emitting light having a short wavelength, while the dibenzocarbazolyl has a higher electron density and is able to satisfy a blue emission wavelength required for an organic light emitting device.
Further, when hydrogen atoms are present on the dibenzo [ c, g ] carbazole in the numbers 4 and 10 as follows, the hydrogen atoms generate repulsive force with the aryl group or heterocyclic group attached to the amine group, thereby interfering with the rotation of the amine group. Therefore, when a compound having the following structure is used as a blue fluorescent dopant, the half width is reduced, and when used in an organic light emitting device, a device having higher color purity can be obtained.
Examples of the substituent in the present specification will be described below, however, the substituent is not limited thereto.
In the context of the present specification, and the dotted line means a site bonded to other substituent or bonding site.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound becomes an additional substituent, and the position of substitution is not limited as long as it is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with one, two or more substituents selected from: deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkenyl group; an alkoxy group; a substituted or unsubstituted phosphine oxide group; an aryl group; and heteroaryl, or substituted with a substituent linked to two or more of the above substituents, or having no substituent. For example, "a substituent to which two or more substituents are attached" may include a biphenyl group. In other words, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.
In the present specification, examples of the halogen group may include fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 50. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. Specific examples thereof may include 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, but are not limited thereto.
In the present specification, an 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. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 40. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl, styryl and the like, but are not limited thereto.
In the present specification, specific examples of the phosphine oxide group may include, but are not limited to, diphenylphosphineoxide, dinaphthylphospheoxide, and the like.
In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specific examples of the monocyclic aryl group may include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 24. Specific examples of the polycyclic aromatic group may include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, perylene, and the like,
In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
When the fluorenyl group is substituted, it may comprise
In the present specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to an atom substituted with the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or another substituent that replaces an atom substituted with the corresponding substituent. For example, two substituents that are ortho-substituted in the phenyl ring and two substituents that substitute the same carbon in the aliphatic ring can be interpreted as groups that are "adjacent" to each other.
In the present specification, a heterocyclic group is a group containing one or more atoms other than carbon (i.e., heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, Si, S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 or 2 to 30. Examples of the heterocyclic group may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
In this specification, the description of aryl provided above may apply to arylene, except that arylene is divalent.
In the present specification, in the substituent, the meaning of "adjacent two are bonded to each other to form a ring" means that a substituted or unsubstituted hydrocarbon ring is formed by bonding with an adjacent group; or a substituted or unsubstituted heterocycle.
In the present specification, a ring means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.
In this specification, a hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a fused ring of aromatic and aliphatic, and may be selected from examples of cycloalkyl or aryl groups, except that the hydrocarbon ring is not monovalent.
In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of aryl groups, except that the aromatic ring is not monovalent.
In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.
In one embodiment of the present specification, Ar1 is phenyl unsubstituted or substituted with alkyl or silyl; biphenyl, unsubstituted or substituted with alkyl or silyl groups; naphthyl unsubstituted or substituted with alkyl or silyl; phenanthryl which is unsubstituted or substituted by alkyl or silyl; dibenzofuranyl unsubstituted or substituted by alkyl or silyl; or dibenzothienyl which is unsubstituted or substituted by alkyl or silyl.
In one embodiment of the present specification, Ar1 is phenyl unsubstituted or substituted with methyl, ethyl, propyl, butyl or trimethylsilyl; biphenyl unsubstituted or substituted with methyl, ethyl, propyl, butyl or trimethylsilyl; naphthyl unsubstituted or substituted by methyl, ethyl, propyl, butyl or trimethylsilyl; phenanthryl which is unsubstituted or substituted by methyl, ethyl, propyl, butyl or trimethylsilyl; dibenzofuranyl which is unsubstituted or substituted by methyl, ethyl, propyl, butyl or trimethylsilyl; or dibenzothienyl which is unsubstituted or substituted by methyl, ethyl, propyl, butyl or trimethylsilyl.
In one embodiment of the present specification, Ar1 is phenyl unsubstituted or substituted with methyl, propyl, butyl or trimethylsilyl; biphenyl unsubstituted or substituted with methyl, propyl, butyl or trimethylsilyl; naphthyl unsubstituted or substituted by methyl, propyl, butyl or trimethylsilyl; phenanthryl which is unsubstituted or substituted by methyl, propyl, butyl or trimethylsilyl; dibenzofuranyl unsubstituted or substituted by methyl, propyl, butyl or trimethylsilyl; or dibenzothienyl which is unsubstituted or substituted by methyl, propyl, butyl or trimethylsilyl.
In one embodiment of the present specification, Ar1 is phenyl unsubstituted or substituted with methyl, propyl, butyl or trimethylsilyl; a biphenyl group; a naphthyl group; phenanthryl; a dibenzofuranyl group; or dibenzothienyl.
In one embodiment of the present description, Ar1 is phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophenyl.
In one embodiment of the present specification, Ar2 to Ar5 are each substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or a substituted or unsubstituted dibenzofuranyl group.
In one embodiment of the present specification, each of Ar2 to Ar5 is phenyl unsubstituted or substituted with a substituent selected from the group consisting of alkyl, silyl, and aryl; biphenyl unsubstituted or substituted with a substituent selected from the group consisting of alkyl, silyl and aryl; or a dibenzofuranyl group which is unsubstituted or substituted by a substituent selected from the group consisting of an alkyl group, a silyl group and an aryl group.
In one embodiment of the present specification, each of Ar2 to Ar5 is phenyl unsubstituted or substituted with a substituent selected from the group consisting of methyl, ethyl, propyl, butyl, trimethylsilyl, and phenyl; biphenyl unsubstituted or substituted with a substituent selected from the group consisting of methyl, ethyl, propyl, butyl, trimethylsilyl, and phenyl; or dibenzofuranyl which is unsubstituted or substituted by methyl, ethyl, propyl, butyl, trimethylsilyl and phenyl.
In one embodiment of the present specification, each of Ar2 to Ar5 is phenyl unsubstituted or substituted with a substituent selected from the group consisting of methyl, ethyl, propyl, butyl, and trimethylsilyl; biphenyl unsubstituted or substituted with a substituent selected from the group consisting of methyl, ethyl, propyl, butyl, and trimethylsilyl; or dibenzofuranyl which is unsubstituted or substituted by methyl, ethyl, propyl, butyl and trimethylsilyl.
In one embodiment of the present specification, R1 and R2 are hydrogen.
In one embodiment of the present specification, the compound of chemical formula 1 is selected from the following structural formulas.
The compound according to one embodiment of the present application may be prepared using a preparation method described later.
For example, the compound of chemical formula 1 may have its core structure prepared from [ intermediate a ] using Buchwald-Hartwig coupling reaction (a method well known in the art) as in the following reaction formula 1 and reaction formula 2. Substituents may be bonded using methods known in the art, and the type, position, or number of substituents may be varied according to techniques known in the art.
[ reaction formula 1]
[ reaction formula 2]
Ar1 to Ar5 of the formulae are as described above.
An embodiment of the present application provides an organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the compound.
In the present specification, the description that one member is placed "on" another member includes not only the case where one member is adjacent to another member but also the case where another member is present between two members.
In this specification, unless specifically stated to the contrary, description of a part "including" a certain constituent element means that another constituent element can also be included, and the another constituent element is not excluded.
The organic material layer of the organic light emitting device of the present application may be formed in a single layer structure, but may also be formed in a multilayer structure in which two or more organic material layers are laminated. For example, as a typical example of the organic light emitting device of the present disclosure, the organic light emitting device 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 material layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic material layers may be included.
In one embodiment of the present application, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
In one embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
In another embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
In one embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.
In one embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.
In one embodiment of the present application, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound.
In one embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
In one embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound as a blue dopant.
In one embodiment of the present application, the light-emitting layer further includes an anthracene-containing compound as a host.
In one embodiment of the present application, the host is represented by the following chemical formula a.
[ chemical formula A ]
In the chemical formula A, the compound represented by the formula A,
ar11 and Ar12 are the same or different from each other and are each independently substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, and
g1 to G8 are the same or different from each other and are each independently hydrogen; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.
In one embodiment of the present specification, G1 to G8 are hydrogen.
In one embodiment of the present specification, Ar11 and Ar12 are the same or different from each other and are each independently substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted biphenyl; substituted or unsubstituted phenanthryl; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted benzonaphthofuranyl group.
In one embodiment of the present specification, Ar11 and Ar12 are the same or different from each other and are each independently phenyl unsubstituted or substituted with phenyl or naphthyl; naphthyl unsubstituted or substituted with phenyl or naphthyl; biphenyl unsubstituted or substituted with phenyl or naphthyl; phenanthryl unsubstituted or substituted with phenyl or naphthyl; dibenzofuranyl unsubstituted or substituted by phenyl or naphthyl; or benzonaphthofuranyl which is unsubstituted or substituted by phenyl or naphthyl.
In one embodiment of the present specification, Ar11 and Ar12 are the same or different from each other and are each independently unsubstituted or naphthyl-substituted phenyl; unsubstituted or phenyl-substituted naphthyl; a biphenyl group; phenanthryl; a dibenzofuranyl group; or benzonaphthofuranyl.
In one embodiment of the present specification, formula a is represented by the following formula a-1.
[ chemical formula A-1]
In formula A-1, Ar11 is a substituted or unsubstituted aryl group,
x is O or S, and X is O or S,
g10 is hydrogen; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or two or more adjacent G10 are bonded to each other to form a substituted or unsubstituted ring, and
p is an integer of 0 to 4, and when p is 2 or more, G10 are the same as or different from each other.
In one embodiment of the present specification, formula a is selected from the following structural formulae.
In one embodiment of the present specification, in chemical formula a-1, Ar11 is a substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, or substituted or unsubstituted phenanthryl.
In one embodiment of the present specification, in chemical formula a-1, Ar11 is unsubstituted or aryl-substituted phenyl, unsubstituted or aryl-substituted naphthyl, unsubstituted or aryl-substituted biphenyl, or unsubstituted or aryl-substituted phenanthryl.
In one embodiment of the present specification, in chemical formula a-1, Ar11 is unsubstituted or naphthyl-substituted phenyl, unsubstituted or phenyl-substituted naphthyl, biphenyl, or phenanthryl.
In one embodiment of the present specification, in formula a-1, G11 is hydrogen, or two or more adjacent G11 are bonded to each other to form a substituted or unsubstituted aromatic ring.
In one embodiment of the present specification, in chemical formula a-1, G11 is hydrogen, or two or more adjacent G11 are bonded to each other to form a substituted or unsubstituted benzene ring.
In one embodiment of the present specification, in chemical formula a-1, G11 is hydrogen, or two or more adjacent G11 are bonded to each other to form an aromatic ring.
In one embodiment of the present specification, in chemical formula a-1, G11 is hydrogen, or two or more adjacent G11 are bonded to each other to form a benzene ring.
In one embodiment of the present specification, formula a-1 is selected from the following structural formulae.
In one embodiment of the present application, the weight ratio of the compound of chemical formula 1 and the host compound represented by chemical formula a is 1:2 to 1: 100.
In one embodiment of the present application, the organic material layer comprising the compound of chemical formula 1 has a thickness of
An organic light emitting device includes: a first electrode; a second electrode disposed opposite to the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic material layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers contains the compound.
In one embodiment of the present application, as the two or more organic material layers, two or more may be selected from an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.
In one embodiment of the present application, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be contained in one of two or more electron transport layers, or may be contained in each of two or more electron transport layers.
Further, in one embodiment of the present application, when the compound is included in each of two or more electron transport layers, materials other than the compound may be the same as or different from each other.
In one embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer including a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group, in addition to the organic material layer including the compound.
In another embodiment, the organic light emitting device may be an organic light emitting device (normal type) having a structure in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate.
In another embodiment, the organic light emitting device may be an organic light emitting device (inverted type) having an inverted structure in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate.
For example, fig. 1 and 2 show the structure of an organic light emitting device according to an embodiment of the present application.
Fig. 1 shows a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are successively laminated. In such a structure, the compound may be contained in the light-emitting layer 3.
Fig. 2 shows a structure of an organic light emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 are successively laminated. In such a structure, the compound may be contained in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.
In such a structure, the compound may be contained in one or more layers of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
The organic light emitting devices of the present application may be fabricated using materials and methods known in the art, except that one or more layers of the organic material layer comprise the compounds of the present application, i.e., the compounds described above.
When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same or different materials from each other.
The organic light emitting device of the present application may be manufactured using materials and methods known in the art, except that one or more layers of the organic material layer include the above-described compound, i.e., the compound represented by chemical formula 1.
For example, the organic light emitting device of the present application can be manufactured by successively laminating a first electrode, an organic material layer, and a second electrode on a substrate. Herein, the organic light emitting device may be manufactured by the following process: an anode is formed on a substrate by depositing a metal, a metal oxide having conductivity, or an alloy thereof using a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a material capable of functioning as a cathode is deposited on the organic material layer. In addition to such a method, the organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
In addition, the compound of chemical formula 1 may be formed as an organic material layer using a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, etc., but is not limited thereto.
In addition to such a method, an organic light emitting device can be manufactured by successively laminating a cathode material, an organic material layer, and an anode material on a substrate (international patent application laid-open No. 2003/012890). However, the manufacturing method is not limited thereto.
In one embodiment of the present application, 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 an anode.
As the anode material, a material having a large work function is generally preferred so that hole injection into the organic material layer is smooth. Specific examples of anode materials that can be used in the present disclosure include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, e.g. ZnO: Al or SnO 2Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred so that electron injection into the organic material layer is smooth. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multilayer construction, e.g. LiF/Al or LiO 2Al; and the like, but are not limited thereto.
The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound of: it has an ability to transport holes, thus having a hole injection effect in the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, preventing excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material, and in addition, an excellent thin film forming ability. The Highest Occupied Molecular Orbital (HOMO) of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanenitrile-based hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.
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 as a hole transport material, a material that can receive holes from the anode or the hole injection layer and move the holes to the light emitting layer, and that has high hole mobility is suitable. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated portions and non-conjugated portions, and the like, but are not limited thereto.
Luminescent materials are materials which: which is capable of emitting light in the visible region by receiving holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining the holes and electrons, and is preferably a material having favorable quantum efficiency for fluorescence and phosphorescence. Specific examples thereof include: 8-hydroxyquinoline aluminum complex (Alq) 3) (ii) a Carbazole series compounds; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is Azole series, benzothiazole series, and benzimidazole series compounds; poly (p-phenylene vinylene) (PPV) series polymers; a spiro compound; a polyfluorene; rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. Host materials include fused aromatic ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocycle-containing compound includes a compound, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like, but the material is not limited thereto.
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 as an electron transport material, a material that can favorably receive electrons from the cathode and move the electrons to the light emitting layer, and that has high electron mobility is suitable. Specific examples thereof include: al complexes of 8-hydroxyquinoline; comprising Alq 3The complex of (1); an organic radical compound; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials include the commonly used materials having a small work function and being followed by an aluminum or silver layer. Specifically, the cathode materialThe material comprises cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.
The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound of: it has an ability to transport electrons, has an effect of injecting electrons from a cathode, has an excellent electron injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to a hole injection layer, and has an excellent thin film forming ability. Specific examples thereof include fluorenones, anthraquinone dimethanes, diphenoquinones, thiopyran dioxides, and the like, Azole, Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
The metal complex compounds include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), chlorogallium bis (2-methyl-8-quinolinolato), gallium bis (2-methyl-8-quinolinato) (o-cresol), aluminum bis (2-methyl-8-quinolinato) (1-naphthol), gallium bis (2-methyl-8-quinolinato) (2-naphthol), and the like, but are not limited thereto.
The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. In particular, comprises
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type, depending on the material used.
EMBODIMENTS FOR CARRYING OUT THE INVENTION
A method for preparing the compound represented by chemical formula 1 and manufacturing an organic light emitting device including the same will be specifically described in the following examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.
[ Synthesis examples ]
< Synthesis example 1> Synthesis of intermediate A
(Synthesis example 1-1) Synthesis of intermediate A-1
In a three-necked flask, naphthalen-1-ylboronic acid (15.0g, 87.2mmol) and 1-bromo-2-nitronaphthalene (23.1g, 91.6mmol) were dissolved in Tetrahydrofuran (THF) (225ml), and the solution in H was introduced thereto 2K in O (113ml) 2CO 3(48.2g, 348.9 mmol). Into which Pd (PPh) was introduced 3) 4(3.0g, 2.6mmol), and the resultant was stirred under reflux for 8 hours under an argon atmosphere. When the reaction was terminated, the resultant was cooled to room temperature, and the reaction solution was transferred to a separatory funnel and then extracted with ethyl acetate. Extracting with MgSO 2 4Dried, then filtered and concentrated, and the sample was purified using silica gel column chromatography to obtain intermediate a-1(22.2g, 85% yield). (MS [ M + H)] +＝299)
(Synthesis example 1-2) Synthesis of intermediate A-2
A2-necked flask was charged with intermediate A-1(20.0g, 66.8mmol), triphenylphosphine (13.9g, 100.2mmol) and o-dichlorobenzene (200ml), and the resultant was stirred under reflux for 12 hours. When the reaction was terminated, the resultant was cooled to room temperature, then distilled in vacuo to remove the solvent, water and CH 2Cl 2And (4) extracting. Extracting with MgSO 2 4Dried, filtered and concentrated, and the sample was purified using silica gel column chromatography to obtain intermediate a-2(12.7g,yield 71%). (MS [ M + H)] +＝267)
(Synthesis examples 1-3) Synthesis of intermediate A
A2-necked flask was charged with intermediate A-2(12.5g, 46.8mmol), N-bromosuccinimide (NBS) (18.3g, 102.9mmol) and Dimethylformamide (DMF) (450mL), and the resultant was stirred at room temperature under argon atmosphere for 5 hours. After the reaction was terminated, the reaction solution was transferred to a separatory funnel, water (300mL) was added thereto, and the resultant was extracted with ethyl acetate. The sample was purified using silica gel column chromatography to obtain intermediate a (9.5g, 48% yield). (MS [ M + H)] +＝425)
In Synthesis example 1-1, when a substituent is bonded to naphthalene-1-ylboronic acid or 1-bromo-2-nitronaphthalene, a compound of chemical formula 1 in which R1 and R2 are bonded can be synthesized.
< Synthesis example 2> Synthesis of Compound 1
(Synthesis example 2-1) Synthesis of Compound 1-1
In a three-necked flask, intermediate a (9.0g, 21.2mmol) and iodobenzene (4.5g, 22.2mmol) were dissolved in toluene (180ml), and after introducing sodium tert-butoxide (3.1g, 31.8mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4mmol) thereto, the resultant was stirred under reflux conditions of an argon atmosphere for 6 hours. When the reaction was terminated, the resultant was cooled to room temperature, and H was introduced thereinto 2O (200ml), the reaction solution was transferred to a separatory funnel and extracted. Extracting with MgSO 2 4Dried, then filtered and concentrated, and the sample was purified using silica gel column chromatography to obtain compound 1-1(9.5g, yield 90%). (MS [ M + H)] +＝501)
In synthesis example 2-1, a compound having a different Ar1 may be synthesized using a compound such as an aryl group having 6 to 30 carbon atoms or a heterocyclic group having 2 to 30 carbon atoms (which may correspond to Ar1) in place of the phenyl group of iodobenzene.
(Synthesis example 2-2) Synthesis of Compound 1
In a three-necked flask, compound 1-1(9.5g, 19.0mmol) and bis (4- (tert-butyl) phenyl) amine (11.7g, 41.7mmol) were dissolved in xylene (190ml), and after introducing sodium tert-butoxide (2.7g, 28.4mmol) and bis (tri-tert-butylphosphine) palladium (0) (0.2g, 0.4mmol) thereto, the resultant was stirred under reflux conditions of an argon atmosphere for 6 hours. When the reaction was terminated, the resultant was cooled to room temperature, and H was introduced thereinto 2O (200ml), the reaction solution was transferred to a separatory funnel and extracted. Extracting with MgSO 2 4Dried and concentrated, and the sample was purified using silica gel column chromatography, followed by sublimation purification to obtain compound 1(5.8g, yield 34%). (MS [ M + H)] +＝902)
< Synthesis example 3> Synthesis of Compound 2
Compound 2 was synthesized using the same method as the synthesis of Compound 1, except that<Synthesis example 2>In (1), iodobenzene is changed to 1- (tert-butyl) -4-iodobenzene, and bis (4- (tert-butyl) phenyl) amine is changed to N-phenyl-4- (trimethylsilyl) aniline. (MS [ M + H)] +＝878)
< Synthesis example 4> Synthesis of Compound 3
Compound 3 was synthesized using the same method as the synthesis of Compound 1, except that<Synthesis example 2>In the process, the iodobenzene is changed into 2-iodonaphthalene. (MS [ M + H)] +＝952)
< Synthesis example 5> Synthesis of Compound 4
Compound 4 was synthesized using the same method as the synthesis of Compound 1, except that<Synthesis example 2>In (1), iodobenzene is changed into 2-bromodibenzo [ b, d ]]Furan and bis (4- (tert-butyl) phenyl) amine to N- (4- (tert-butyl) phenyl) -3-methylaniline. (MS [ M + H)] +＝908)
< Synthesis example 6> Synthesis of Compound 5
Compound 5 was synthesized using the same method as the synthesis of Compound 1, except that<Synthesis examples 2-2>In the method, bis (4- (tert-butyl) phenyl) amine is changed into N- (m-tolyl) dibenzo [ b, d]Furan-4-amine. (MS [ M + H)] +＝886)
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