CN111683956B - Compound and organic light emitting device comprising the same - Google Patents
Compound and organic light emitting device comprising the same Download PDFInfo
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Abstract
The present specification relates to compounds of chemical formulas 101 to 105 and an organic light emitting device including the same.
Description
Technical Field
The present invention claims priority from korean patent application No. 10-2018-0055103, filed to korean patent office on 5-14 th 2018, the entire contents of which are included in the present specification.
The present specification relates to a compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides compounds and organic light emitting devices comprising the same.
Solution to the problem
According to an embodiment of the present specification, a compound represented by any one of the following chemical formulas 101 to 105 is provided.
[ chemical formula 101]
[ chemical formula 102]
[ chemical formula 103]
[ chemical formula 104]
[ chemical formula 105]
In the above-mentioned chemical formulas 101 and 102,
X 3 and X 4 One of them is N, the others are CR,
in the above-mentioned chemical formulas 103 and 104,
X 1 and X 4 One of them is N, the others are CR,
in the above-mentioned chemical formula 105,
X 1 and X 2 One of them is N, the others are CR,
in the above-mentioned chemical formulas 101 to 105,
m is Ir or Pt, and the M is Ir or Pt,
a is a substituted or unsubstituted six-membered hydrocarbon ring or a substituted or unsubstituted five-or six-membered heterocyclic ring,
l1 and L2 combine with each other to form a substituted or unsubstituted ring,
r1 and R are the same or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted phosphine oxide group, or adjacent substituents are bonded to each other to form a ring,
n is an integer of 0 to 6,
l is an integer of 0 to 4,
m is 1 or 2, o is 1 or 2, m+o is not more than 3,
when n and l are plural, R1 are the same or different from each other,
when m and o are plural, the ligands in brackets may be the same or different from each other.
In addition, the present specification provides an organic light emitting device, including: a first electrode, a second electrode, and an organic layer having 1 or more layers between the first electrode and the second electrode, wherein 1 or more layers of the organic layer having 1 or more layers contain the compounds of the chemical formulas 101 to 105.
Effects of the invention
The compound according to an embodiment of the present specification can be used as a material of an organic layer of an organic light-emitting device, and by using the compound, improvement of efficiency, high color purity, and improvement of lifetime characteristics can be achieved in the organic light-emitting device.
Drawings
Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.
Fig. 2 illustrates an organic light emitting device according to an embodiment of the present specification.
[ description of the symbols ]
1: substrate board
2: first electrode
3: organic layer
4: light-emitting layer
5: second electrode
Detailed Description
The present specification will be described in more detail below.
The present specification provides compounds represented by the above chemical formulas 101 to 105.
In the structure of the above chemical formula, the bonding strength between the ligand and the metal is improved, and the vibration level is reduced, whereby the half-width is reduced while high luminous efficiency can be provided. Also, as the position of the substituent of R1 is far from the metal atom, the size of the molecule becomes large, thereby preventing aggregation between dopants, reducing the self-quenching effect, and thus increasing the lifetime. Therefore, by using the structure of the present invention as a light emitting material of an organic layer, improvement in efficiency, high color purity, and improvement in lifetime characteristics can be achieved in an organic light emitting device.
In the above chemical formula, the ligand comprising L1 and L2 and the structure in brackets represented by the above repetition number m, namely
Structurally different. The same ligand, i.e. homoligand complexes comprising 3 identical ligands, emit light in a uniform direction, in contrast to the same, comprising mutually different structuresThe heterogeneous ligand complex of the ligand of (2) has a high efficiency of light emission due to a large light emission orientation in the vertical direction. Therefore, in the above chemical formula 1, m is preferably 1 or 2.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted silyl group, substituted or unsubstituted aryl group, and substituted or unsubstituted heteroaryl group, or substituted with a substituent in which 2 or more substituents out of the above-exemplified substituents are linked, or does not have any substituent. For example, the "substituent in which 2 or more substituents are linked" may be aryl substituted with aryl, aryl substituted with heteroaryl, heteroaryl substituted with aryl, aryl substituted with alkyl, or the like.
In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be a linear or branched alkyl group, and may be a cycloalkyl group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, 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, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto. The cyclic alkyl group may contain a cycloalkyl group having 3 to 30 carbon atoms, and may be, for example, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, or the like.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be a single ring or a multiple ring.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or the like, but is 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 30. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl,
A group, a fluorenyl group, etc., but is not limited thereto.
In the present specification, the above fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In this specification, a heteroaryl group contains 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the heteroatoms may contain 1 or more atoms selected from O, N, se, S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl, (-) -and (II) radicals>
Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->
Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the hydrocarbon ring means an aromatic or aliphatic hydrocarbon ring, and may be a six-membered ring. Examples of the aryl group include the aromatic hydrocarbon ring described above, except that the aromatic hydrocarbon ring is not a 1-valent group.
In the present specification, a heterocyclic ring means an aromatic or aliphatic ring containing one or more hetero atoms, and may be a five-membered or six-membered ring. Examples of heteroaryl groups described above may be used for the heterocyclic ring described above, except that the heterocyclic ring is not a 1-valent group.
According to one embodiment of the present disclosure, M is Ir.
According to an embodiment of the present specification, R is hydrogen.
According to an embodiment of the present specification, R1 is hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
According to an embodiment of the present specification, R1 is hydrogen, deuterium, or an alkyl group substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, R1 is hydrogen or an alkyl group having 1 to 10 carbon atoms.
According to an embodiment of the present specification, R1 is hydrogen, a linear alkyl group having 1 to 10 carbon atoms, or a branched alkyl group having 1 to 10 carbon atoms.
According to one embodiment of the present specification, R1 is hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, or hexyl.
For example, according to an embodiment of the present invention, when the compounds of the present invention are chemical formulas 101-1 to 105-1 below, as the position of the substituent of R1 is away from the metal atom, the size of the molecule becomes larger, aggregation between dopants is prevented, thereby reducing self-quenching effect, and thus increasing lifetime.
[ chemical formula 101-1]
[ chemical formula 102-1]
[ chemical formula 103-1]
[ chemical formula 104-1]
[ chemical formula 105-1]
In the above chemical formulas 101-1 to 105-1, the definitions of X1 to X4, L1, L2, R1, A, M, m and o are the same as those in the above chemical formulas 101 to 105,
n is an integer of 0 to 4,
l is an integer from 0 to 2.
According to an embodiment of the present specification, the above L1 and L2 may be combined with each other to form a structure of the following chemical formula 1-1 or 1-2 including M.
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2,
m is Ir or Pt, and the M is Ir or Pt,
ra to Rk are the same or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted phosphine oxide group.
According to an embodiment of the present specification, ra to Rc are the same as or different from each other, and each is independently hydrogen, deuterium, or an alkyl group substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, ra to Rc are the same as or different from each other, and each independently is hydrogen or an alkyl group having 1 to 10 carbon atoms.
According to an embodiment of the present specification, ra to Rc are the same as or different from each other, and each independently is hydrogen, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms.
According to an embodiment of the present specification, ra and Rb are the same or different from each other, each independently is a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms, and Rc is hydrogen.
According to an embodiment of the present specification, ra and Rb are the same as each other, and are a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 1 to 10 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms, and Rc is hydrogen.
According to an embodiment of the present specification, ra to Rc are the same as each other, and are a linear alkyl group having 1 to 10 carbon atoms or a branched alkyl group having 1 to 10 carbon atoms.
According to an embodiment of the present specification, rd to Rk are the same as or different from each other, and are each independently hydrogen, deuterium, or an alkyl group substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, re and Ri are the same or different from each other, each independently is an alkyl group substituted or unsubstituted with deuterium, rf is hydrogen, deuterium, or an alkyl group substituted or unsubstituted with deuterium, rd, rg, rh, rj and Rk are hydrogen or deuterium.
According to an embodiment of the present specification, re and Ri are identical to each other, are alkyl groups substituted or unsubstituted with deuterium, rf is hydrogen, alkyl groups substituted or unsubstituted with deuterium, rd, rg, rh, rj and Rk are hydrogen.
According to one embodiment of the present specification, the above
May be represented by the following chemical formula 106 or the following chemical formula 107.
[ chemical formula 106]
[ chemical formula 107]
In the above-mentioned chemical formulas 106 and 107,
* Is a site to which M of chemical formulas 101 to 105 is bound,
ra to Rk are the same or different from each other and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted phosphine oxide group,
o is either 1 or 2 and,
when o is 2, the ligands in brackets are the same or different from each other.
According to one embodiment of the present specification, m is 1.
According to an embodiment of the present specification, m is 2.
According to one embodiment of the present disclosure, m is 1 or 2, and m+o is 3.
According to one embodiment of the present specification, m is 2 and o is 1.
According to an embodiment of the present specification, the above-mentioned a is a six-membered hydrocarbon ring or a five-or six-membered heterocyclic ring, and the above-mentioned six-membered hydrocarbon ring or five-or six-membered heterocyclic ring is substituted or unsubstituted with any one or more substituents selected from deuterium, nitrile group, halogen group, alkyl group substituted with deuterium, aryl group, heteroaryl group and arylamine group.
According to an embodiment of the present specification, a is a six-membered hydrocarbon ring or a five-or six-membered heterocyclic ring, and the six-membered hydrocarbon ring or the five-or six-membered heterocyclic ring is substituted or unsubstituted with deuterium or an alkyl group substituted or unsubstituted with deuterium.
According to one embodiment of the present specification, a is a benzene ring or a five-membered monocyclic heterocycle, and the benzene ring or the five-membered monocyclic heterocycle is substituted or unsubstituted with deuterium or an alkyl group substituted or unsubstituted with deuterium.
According to an embodiment of the present specification, a is a benzene ring substituted or unsubstituted with an alkyl group substituted with an alkyl group or deuterium, or a thiazole group substituted or unsubstituted with an alkyl group substituted with an alkyl group or deuterium.
According to an embodiment of the present specification, a is a benzene ring substituted or unsubstituted with one or more alkyl groups substituted with alkyl groups or deuterium, or a thiazole group substituted or unsubstituted with alkyl groups substituted with alkyl groups or deuterium.
According to an embodiment of the present specification, a is a benzene ring substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms or deuterium, or a thiazole group substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms or deuterium.
According to an embodiment of the present specification, a is a benzene ring substituted or unsubstituted with one or two alkyl groups having 1 to 6 carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms or deuterium, or a thiazole group substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms or deuterium.
According to one embodiment of the present specification, the above
May be represented by the following chemical formula 108 or the following chemical formula 109.
[ chemical formula 108]
[ chemical formula 109]
In the above-mentioned chemical formulas 108 and 109,
* Is a site to which the rings of formulas 101 to 105 where M and X1 to X4 are located are attached,
rm and Rn are each hydrogen, deuterium, or an alkyl group substituted or unsubstituted with deuterium, a is an integer of 0 to 4, and Rm is the same or different from each other when a is plural.
According to an embodiment of the present description, rm and Rn are each an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with deuterium, and a is 0, 1 or 2.
According to another embodiment of the present specification, the compounds of the above chemical formulas 101 to 105 may be represented by the following structural formulas.
If the production formula described in the examples of the present specification and the above intermediates are appropriately combined based on common technical knowledge, all the above-described compounds of the present invention described in the present specification can be produced.
The organic light-emitting device of the present invention can be manufactured by a usual method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention is an organic light-emitting device including a first electrode, a second electrode provided opposite to the first electrode, and 1 or 2 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers may contain the compound.
However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
For example, the structure of the organic light emitting device of the present invention may have the structure shown in fig. 1, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic layer 3, and a second electrode 5 are sequentially stacked on a substrate 1. In fig. 1 described above, the organic layer 3 may contain the compound of the present invention described above.
Fig. 2 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic layer 3, a light emitting layer 4, and a second electrode 5 are sequentially stacked on a substrate 1. The light-emitting layer 4 of fig. 2 may contain the compound of the present invention. The organic layer 3 may include a layer having an additional function, such as a hole injection layer, a hole transport layer, or an electron blocking layer, in addition to the light emitting layer.
The structure is not limited to the structure of fig. 2, and an additional organic layer, such as a hole blocking layer, an electron transport layer, or an electron injection layer, may be further included between the light emitting layer 4 and the second electrode 5.
The organic light-emitting device of the present invention includes a structure in which a first electrode, an organic layer, and a second electrode are sequentially stacked on a substrate, and the organic layer may contain the compound of the present invention.
In one embodiment of the present specification, the organic layer may include 1 or more light-emitting layers, and 1 or more of the 1 or more light-emitting layers may include the compound of the present invention.
According to a specific example, the organic light emitting device according to an embodiment of the present invention may have a structure in which an anode, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode are sequentially stacked, and may further include an electron blocking layer provided between the hole transporting layer and the light emitting layer, and a hole blocking layer provided between the light emitting layer and the electron transporting layer. Further, the anode may further include a p-type doped layer including a p-type dopant, which is provided between the anode and the hole transport layer. The electron transport layer may include an n-type dopant. The p-type dopant and the n-type dopant each comprise 1 to 40 wt% based on 100 wt% of the layer. The p-type dopant and the n-type dopant may be materials known in the art, and for example, as the n-type dopant, an alkali metal complex such as Liq may be used.
In one embodiment of the present specification, the light-emitting layer containing the above-described compound of the present invention is a red light-emitting layer.
In one embodiment of the present specification, the compound of the present invention is contained in the light-emitting layer as a dopant.
In one embodiment of the present invention, the compound of the present invention is contained in the light-emitting layer containing the compound in an amount of 1 to 20 parts by weight based on 100 parts by weight of the total light-emitting layer containing the compound.
According to an embodiment of the present specification, the light-emitting layer including the compound of the present invention may include an additional host material. As an example, the light emitting layer may include a compound of the following chemical formula B.
[ chemical formula B ]
In the above-mentioned chemical formula B, the amino acid,
ara and Arb are the same or different from each other and are each independently an aryl group substituted or unsubstituted with a heteroaryl group or an heteroaryl group substituted or unsubstituted with an aryl group,
R 101 and R is 102 Each of which is the same or different from the other, is independently hydrogen, deuterium, aryl substituted or unsubstituted by heteroaryl, or heteroaryl substituted or unsubstituted by aryl, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, b and c are each an integer of 0 to 4.
According to one example, the above formula B may be represented by the following formula B-1.
[ chemical formula B-1]
In the above chemical formula B-1, ara, arb, R, R102 and c are as defined above, and d is an integer of 0 to 6.
According to one example, ara is an N-containing heterocycle substituted with an aryl group, and Arb is an aryl group.
According to another example, ara is a quinazolinyl substituted with phenyl, and Arb is phenyl.
In one embodiment of the present invention, the compound of the present invention is contained in 1 or more layers of a hole injection layer, a hole transport layer, a layer that performs hole injection and transport simultaneously, and a hole adjustment layer.
In one embodiment of the present invention, the compound of the present invention is contained in 1 or more layers among an electron injection layer, an electron transport layer, a layer in which electron injection and transport are performed simultaneously, and an electron modulation layer.
The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
According to an embodiment of the present specification, the compound of the present invention may be manufactured according to the following reaction scheme, but is not limited thereto. In the following reaction formulae, regarding the kind and number of substituents, a person skilled in the art can synthesize various intermediates according to appropriately selecting known starting materials. The kind of reaction and the reaction conditions may be employed by techniques known in the art.
[ reaction type ]
In the above reaction formula, the definitions of X to X4, A, and Ra to Rc are the same as those described above. Ligands having pyridine structures may be used instead as desired
/>
In the following examples, the production of an organic light-emitting device using the above-described compound of the present invention is specifically described. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Modes for carrying out the invention
Production example
Production example 1: production of intermediate 1
In a three-necked flask, 10-chloro-3- (3, 5-dimethylphenyl) benzo [ f]Quinoxaline (20.0 g,62.7 mmol), isobutylboronic acid (7.0 g,69.0 mmol), pd (OAc) 2 (0.6g，2.5mmol)、PCy 3 (1.4g，5.0mmol)、K 3 PO 4 (40.0 g,188.2 mmol) and 200ml of toluene are stirred under reflux under argon for 8 hours. Cooling to normal temperature after the reaction is finished, and using a diatomite plug
) After the filtrate was concentrated, the sample was purified by silica gel column chromatography and distilled to obtain 13.2g of intermediate 1. (yield 62%, MS [ M+H ]] + ＝340)
Production example 2: production of intermediate 2
In a dry three-necked flask, 10-chloro-4- (3, 5-dimethylphenyl) benzo [ h ] was added]Quinazoline (20.0 g,62.7 mmol), iron (III) acetylacetonate (1.1 g,3.1 mmol), 400ml of tetrahydrofuran, 40ml of NMP were slowly added dropwise under nitrogen at 0℃with stirring to a 2.0M solution of magnesium chloride in tetrahydrofuran (63 ml,125.5 mmol). At the end of the dropwise addition, 0℃was maintained while stirring for a further 3 hours. At the end of the reaction, water was slowly added, transferred to a separatory funnel, and extracted with ethyl acetate. The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography and distilled to obtain 11.3g of intermediate 2. (yield 55%, MS [ M+H ]] + ＝326)
Production example 3: production of intermediate 3
In a three-necked flask, 1- (3, 5-bis (methyl-d 3) phenyl) -8-chlorobenzo [ f]Quinazoline (20.0 g,61.6 mmol), isobutyl boronic acid (6.9 g,67.7 mmol), pd (OAc) 2 (0.6g，2.5mmol)、PCy 3 (1.4g，4.9mmol)、K 3 PO 4 (39.2 g,184.7 mmol) and 200ml of toluene were stirred under reflux in an argon atmosphere for 8 hours. After cooling to room temperature at the end of the reaction, the filtrate was concentrated by a celite plug, and the sample was purified by silica gel column chromatography and distilled to obtain 14.3g of intermediate 3. (yield 67%, MS [ M+H)] + ＝347)
Production example 4: production of intermediate 4
1) Production of intermediate 4-a
In a three-necked flask, 3-bromo-10-chlorobenzo [ f]Quinoxaline (20.0 g,68.1 mmol), (3- (tert-butyl) phenyl) boronic acid (13.3 g,74.9 mmol)) Dissolved in 300ml of tetrahydrofuran, K was added 2 CO 3 (37.7 g,272.5 mmol) dissolved in 150ml H 2 O is added. Pd (PPh) was added thereto 3 ) 4 (3.1 g,2.7 mmol) was stirred under reflux for 8 hours under argon. After cooling to room temperature at the end of the reaction, the reaction solution was transferred to a separating funnel and extracted with water and ethyl acetate. The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography, whereby 17.0g of intermediate 4-a was obtained. (yield 72%, MS [ M+H ]] + ＝347)
2) Production of intermediate 4
In a three-necked flask, intermediate 4-a (17.0 g,49.0 mmol), K 3 PO 4 (31.2 g,147.0 mmol) was dissolved in 340ml toluene, 34ml H 2 O is added. The reaction was purged with nitrogen for 20 minutes, and 2,4, 6-trimethyl-1,3,5,2,4,6-trioxadiborane (7.54 ml,53.9 mmol) and Pd were added 2 (dba) 3 (0.4 g,0.5 mmol) and S-Phos (2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl) (0.8 g,2.0 mmol) were stirred under reflux in an argon atmosphere for 18 hours. After cooling to room temperature at the end of the reaction, 200ml of water was added, and the mixture was transferred to a separating funnel to extract an organic layer. The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography, whereby 10.2g of intermediate 4 was obtained. (yield 64%, MS [ M+H ]] + ＝326)
Production example 5: production of intermediate 5
In a three-necked flask, 4-chloro-6,7,10-trimethylbenzo [ h ]]Quinazoline (13.0 g,50.6 mmol), (3- (tert-butyl) phenyl) boronic acid (9.9 g,55.7 mmol) was dissolved in 195ml of tetrahydrofuran and K was taken up 2 CO 3 (28.0 g,202.5 mmol) was dissolved in 98mH of l 2 O is added. Pd (PPh) was added thereto 3 ) 4 (2.3 g,2.0 mmol) was stirred under reflux for 8 hours under argon. After cooling to room temperature at the end of the reaction, the reaction solution was transferred to a separating funnel and extracted with water and ethyl acetate. The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography to obtain 10.5g of intermediate 5. (yield 60%, MS [ M+H ]] + ＝347)
Production example 6: production of intermediate 6
1) Production of intermediate 6-a
In a three-necked flask, 2-bromo-10-chlorobenzo [ h]Quinazoline (20.0 g,68.1 mmol), (4- (tert-butyl) phenyl) boronic acid (13.3 g,74.9 mmol) was dissolved in 300ml of tetrahydrofuran and K was taken up 2 CO 3 (37.7 g,272.5 mmol) dissolved in 150ml H 2 O is added. Pd (PPh) was added thereto 3 ) 4 (3.1 g,2.7 mmol) was stirred under reflux for 8 hours under argon. After cooling to room temperature at the end of the reaction, the reaction solution was transferred to a separating funnel and extracted with water and ethyl acetate. The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography, whereby 17.7g of intermediate 6-a was obtained. (yield 75%, MS [ M+H ]] + ＝347)
2) Production of intermediate 6
In a three-necked flask, intermediate 6-a (17.0 g,49.0 mmol), K 3 PO 4 (31.2 g,147.0 mmol) dissolved in 340ml toluene, 34ml H 2 O is added. The reaction was purged with nitrogen for 20 minutes, and 2,4, 6-trimethyl-1,3,5,2,4,6-trioxadiborane (7.54 ml,53.9 mmol) and Pd were added 2 (dba) 3 (0.4 g,0.5 mmol) and S-Phos(2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl) (0.8 g,2.0 mmol) was stirred under reflux for 18 hours under argon atmosphere. After cooling to room temperature at the end of the reaction, 200ml of water was added, and the mixture was transferred to a separating funnel to extract an organic layer. The extract was treated with MgSO 4 After drying, filtration and concentration, the sample was purified by silica gel column chromatography, whereby 10.7g of intermediate 6 was obtained. (yield 67%, MS [ M+H)] + ＝326)
Production example 7: production of Compound 1-a
1) Production of Compound 1-a
In a three-necked flask, intermediate 1 (10.0 g,29.4 mmol), iridium (III) chloride hydrate (5.0 g,12.9 mmol), 135ml of 2-ethoxyethanol, 45ml of H were added 2 O, stirring for 12 hours under reflux of argon atmosphere. At the end of the reaction, the reaction mixture was cooled to room temperature, and the precipitate was filtered, washed with methanol, dried and used in the next reaction without further purification. (13.0 g, yield 98%)
2) Production of Compound 1
In a three-necked flask, compound 1-a (13.0 g,7.2 mmol), 2, 6-tetramethylheptane-3, 5-dione (13.2 g,71.7 mmol), K were added 2 CO 3 (9.9 g,71.7 mmol) and 90ml of 2-ethoxyethanol, and stirred at room temperature for 24 hours. After filtration at the end of the reaction, the mixture was washed with MeOH and dissolved in CH 2 Cl 2 Thereafter, the mixture was filtered through a celite plug. Then, using CH 2 Cl 2 And isopropanol, and finally 4.8g of compound 1 was obtained by sublimation purification. (yield 32%, MS [ M+H ]] + ＝1054)
Production example 8: production of Compound 2
In production example 7, 5.0g of compound 2 was produced by the same method as that for compound 1, except that intermediate 2 was used instead of intermediate 1 and 3, 7-diethylnonane-4, 6-dione was used instead of 2, 6-tetramethylheptane-3, 5-dione. (MS [ M+H)] + ＝1054)
Production example 9: production of Compound 3
In production example 7, 4.8g of compound 3 was produced by the same method as that for the production of compound 1, except that intermediate 3 was used in place of intermediate 1 and 2, 6-tetramethylheptane-3, 5-dione was used in place of 2, 6-dimethylnonane-4, 6-dione. (MS [ M+H)] + ＝1066)
Production example 10: production of Compound 4
In production example 7, 4.9g of compound 4 was produced by the same method as the production method of compound 1, except that intermediate 4 was used instead of intermediate 1. (MS [ M+H)] + ＝1026)
Production example 11: production of Compound 5
In production example 7, 4.9g of compound 5 was produced by the same method as the production method of compound 1, except that intermediate 5 was used instead of intermediate 1 and 3, 7-diethylnonane-4, 6-dione was used instead of 2, 6-tetramethylheptane-3, 5-dione. (MS [ M+H)] + ＝1111)
Production example 12: production of Compound 6
In production example 7, 4.9g of compound 6 was produced by the same method as the production method of compound 1, except that intermediate 6 was used instead of intermediate 1. (MS [ M+H)] + ＝1026)
Experimental example
Experimental example 1
ITO (Indium Tin Oxide) to
The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, decon (Fisher Co.) from Fei Hill was used as the detergent TM The product of CON705, distilled water, was filtered twice using a 0.22 μm sterile filter (0.22 μm sterilizing filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is finished, the plasma cleaning machine is respectively used for ultrasonic washing for 10 minutes by using solvents of isopropanol, acetone and methanol, and the plasma cleaning machine is used for drying the plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following mixture of 95% by weight of HT-A and 5% by weight of P-DOPANT was prepared
Is subjected to thermal vacuum evaporation, and then HT-A alone is used as +.>
And vapor deposition is performed to form a hole transport layer. On the hole transport layer, HT-B as described below is added +.>
And performing thermal vacuum evaporation to form an electron blocking layer. Next, 98 wt% RH as a host and 2 wt% of [ compound 1] as a dopant were applied to the electron blocking layer]Is>
And vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. Next, on the light-emitting layer, the following ET-A is added +.>
Vacuum deposition is performed to form a hole blocking layer. Next, on the hole blocking layer, the following ET-B and Liq are mixed in a weight ratio of 2:1 to +.>
To form an electron transport layer by thermal vacuum evaporation, and then mixing LiF and magnesium in a weight ratio of 1:1 to +.>
And vacuum vapor deposition is performed to form an electron injection layer. On the electron injection layer, magnesium and silver are mixed in a weight ratio of 1:4, and then +.>
And vapor deposition is performed to form a cathode, thereby manufacturing an organic light-emitting device. />
Experimental examples 2 to 6
An organic light-emitting device was fabricated by the same method as in example 1 above, except that the compound described in table 1 below was used instead of the compound 1.
Comparative examples 1 to 7
An organic light-emitting device was fabricated by the same method as in example 1 above, except that the compound described in table 1 below was used instead of the compound 1. In Table 1 below, RD-1 through RD-7 are each as follows.
The organic light emitting devices manufactured in the above experimental examples and comparative experimental examples were subjected to current application, and voltage, efficiency, emission spectrum, and lifetime (T97) were measured, respectively, and the results thereof are shown in table 1 below. Here, the voltage and the efficiency are increased by applying 10mA/cm 2 The half-peak width is measured based on the obtained luminescence spectrum. Lifetime (T97) is at 20mA/cm 2 The time required for the initial brightness to decrease to 97% at the current density of (c). The respective values are expressed in terms of relative proportions with respect to the value of comparative example 1.
TABLE 1
The compound of the present invention has a structure in which one more nitrogen element is present as an electron acceptor in the quinoline structure of comparative example 1, and one more benzene ring is fused as an electron donor. These two effects are known to have appropriate energy levels against each other, and thus have voltages similar to those of comparative example 1. When the energy level is changed, electrons or holes are trapped and the voltage is increased and the wavelength is changed, so that the performance suitable for the red light emitting device cannot be exhibited.
In the compound of the present invention, the binding strength between the ligand and the metal is improved, and the vibrational energy level is reduced, thereby bringing about high efficiency while the half-width is reduced. Also, as the position of the substituent of R1 is far from the metal atom, the size of the molecule becomes large, thereby preventing aggregation between dopants, reducing the self-quenching effect, and thus increasing the lifetime.
In contrast to the homogeneous ligand conjugate such as RD-2 of comparative example 2, which had uniform light emission, the heterogeneous ligand conjugates such as compounds 1 to 6 had greater light emission orientation in the vertical direction and thus had higher light emission efficiency.
It is understood that in the case of comparative example 3 in which the portion corresponding to a in the chemical formulas 101 to 105 of the present invention is benzofuran, a relatively high voltage, low efficiency and a low lifetime are exhibited, compared to the case of phenyl.
The number of nitrogen elements functioning as electron acceptors in comparative examples 4 and 5 is different from that of the present invention, and therefore, the voltage is high, the efficiency is low, and the lifetime is also reduced as compared with the compound of the present invention.
It is found that the lifetime of comparative examples 6 and 7 is reduced as compared with the case of using compound 2 having a different position of the alkyl substituent in the same core structure (experimental example 2).
Therefore, as can be seen from [ Table 1], when the substance of the present invention is applied as a dopant for a light-emitting layer of an organic electroluminescent device, a device having high efficiency, high color purity and long life can be obtained.
Claims (5)
1. A compound which is any one selected from the following compounds:
2. an organic light emitting device, comprising: a first electrode, a second electrode, and an organic layer having 1 or more layers between the first electrode and the second electrode, wherein the compound according to claim 1 is contained in 1 or more layers of the organic layer.
3. The organic light-emitting device according to claim 2, wherein the organic layer comprises 1 or more light-emitting layers, and 1 or more layers of the light-emitting layers contain the compound.
4. The organic light-emitting device according to claim 3, wherein the light-emitting layer containing the compound is a red light-emitting layer.
5. The organic light-emitting device according to claim 3, wherein the compound is contained in an amount of 1 part by weight or more and 20 parts by weight or less based on 100 parts by weight of a total of light-emitting layers containing the compound.
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| US11739110B2 (en) * | 2019-11-05 | 2023-08-29 | Luminescence Technology Corp. | Organic electroluminescent material and device |
| KR20210079766A (en) * | 2019-12-20 | 2021-06-30 | 삼성전자주식회사 | Organometallic compound and organic light emitting device including the same |
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| CN103665048B (en) * | 2012-09-05 | 2016-05-18 | 清华大学 | One metal complexes and the application in organic electroluminescence device |
| CN106432350A (en) * | 2016-09-02 | 2017-02-22 | 瑞声光电科技(常州)有限公司 | Iridium complex, preparation method thereof and electroluminescent device applying iridium complex |
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| WO2010031738A1 (en) * | 2008-09-22 | 2010-03-25 | Basf Se | Electroluminescent metal complexes with azapyrenes |
| CN107722065A (en) * | 2017-11-15 | 2018-02-23 | 烟台显华光电材料研究院有限公司 | One kind is used as transient metal complex, its preparation method and the application of phosphor material |
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