CN111153811B - Organic compound and organic electroluminescent element comprising same - Google Patents

Organic compound and organic electroluminescent element comprising same Download PDF

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CN111153811B
CN111153811B CN201911079765.8A CN201911079765A CN111153811B CN 111153811 B CN111153811 B CN 111153811B CN 201911079765 A CN201911079765 A CN 201911079765A CN 111153811 B CN111153811 B CN 111153811B
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CN111153811A (en
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郑在皓
姜炫彬
都光石
兪智雄
朴富培
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Material Science Co Ltd
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Material Science Co Ltd
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  • Electroluminescent Light Sources (AREA)

Abstract

The present invention relates to a novel organic compound and an organic light-emitting element comprising the same, and more particularly, to an organic compound excellent in life, efficiency, electrochemical stability and thermal stability and an organic electroluminescent element comprising the same.

Description

Organic compound and organic electroluminescent element comprising same
Technical Field
The present invention relates to a novel organic compound and an organic electroluminescent element comprising the same.
Background
Compared with other flat panel display elements such as conventional Liquid Crystal Displays (LCDs), plasma Display Panels (PDPs), and Field Emission Displays (FEDs), the organic electroluminescent element (OLED) has a simple structure, has various advantages in the manufacturing process, has high brightness and excellent viewing angle characteristics, has a fast response speed, and is actively developed and commercialized due to a low driving voltage, so that it can be used as a light source for flat panel displays such as wall-mounted televisions or backlights, illuminations, billboards, etc. of the displays.
Organic electroluminescent devices were originally reported by Tang (C.W.Tang) et al from Yisman Kodak, (C.W.Tang S.A.Vanslyke, applied physical communication (Applied Phy sics Letters), page 51, 1987), the light emission principle of which is generally based on the recombination of holes injected from a positive electrode and electrons injected from a negative electrode when a voltage is applied, to form excitons, i.e., electron-hole pairs, by transferring the energy of the excitons to a light emitting material for conversion into light.
More specifically, the organic electroluminescent element has a structure including a negative electrode (electron injection electrode) and a positive electrode (hole injection electrode), and one or more organic layers between the two electrodes. At this time, the organic electroluminescent element is laminated in order of a hole injection layer (hole injection layer, HIL), a hole transport layer (hole transport layer, HTL), a light emitting layer (light emitting layer, EML), an electron transport layer (electron transport layer, ETL) or an electron injection layer (electron inject ion layer, EIL) from the positive electrode, and an electron blocking layer (ele ctron blocking layer, EBL) or a hole blocking layer (hole blocking layer, HBL) may be further included before and after the light emitting layer, respectively, in order to improve the efficiency of the light emitting layer.
The organic layer used in the organic electroluminescent element is mostly a pure organic substance or a complex compound of an organic substance and a metal, and may be classified into a hole injecting substance, a hole transporting substance, a light emitting substance, an electron transporting substance, an electron injecting substance, and the like according to the purpose.
Among them, as the hole injecting substance or the hole transporting substance, an organic substance which is easily oxidized and has an electrochemical stable state during oxidation is mainly used. As the electron injecting substance or the electron transporting substance, an organic substance which is easily reduced and has an electrochemical stable state during reduction is mainly used.
On the other hand, the light-emitting layer substance is preferably a substance having a stable state in both the oxidation state and the reduction state, and preferably a substance having high light emission efficiency for converting the light into light when an excitation is formed. More specifically, the light emitting layer is composed of two substances, host (host) and dopant (dopant), the dopant is required to have high quantum efficiency, and the host substance preferably has a larger energy gap than the dopant substance to promote transfer of energy to the dopant. A Display (Display) for a Television (TV), a Mobile device (Mobile), etc. implements Full colors (Full colors) in three colors of red, green, and blue, and a light emitting layer is composed of a red host/dopant, a green host/dopant, and a blue host/dopant, respectively.
Among the conventional substances used for blue dopants, the use of fluorescent molecules such as Perylene (Perylene), coumarin (Coumarine), anthracene (Anthracene), pyrene (Pyrene) and the like occupies a large proportion, but the use of pure blue light is difficult in element fabrication because of the wide emission spectrum and half-amplitude (Full width half the maximum) of the dopant. This characteristic not only reduces the efficiency of Blue in the element resonant structure, but also is a major cause of difficulty in using Deep Blue (Deep Blue) intervals.
Therefore, there is a need to develop a novel dopant capable of solving the problem of concentration extinction at the time of manufacturing an element while maintaining a narrow light emission spectrum and half-amplitude, which is a major cause of efficiency reduction according to the concentration of the dopant and long wavelength of color coordinates.
Prior art literature
Patent literature
Patent document 0001: KR10-2012-0096102A1
Disclosure of Invention
Problems to be solved by the invention
The object of the present invention is to provide a novel organic compound and an organic electroluminescent element comprising the same.
Another object of the present invention is to provide an organic electroluminescent element having a low driving voltage and excellent lifetime characteristics by using an organic compound having a pyrene structure substituted with deuterium and having excellent lifetime, efficiency and electrochemical stability.
Another object of the present invention is to provide a blue host/dopant system and an organic electroluminescent element suitable for the blue series of AM-OLEDs using the organic compound.
Solution for solving the problem
To achieve the object, the present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
Wherein,
n, m, o and p are identical or different from each other and are each independently an integer from 1 to 2,
L 1 L and L 2 Are identical or different from each other and are each independently a single bond, an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 6 to 30 carbon atomsThe base group of the modified polyester resin is a modified polyester resin,
Ar 1 to Ar 4 Each of which is the same or different from the other and is selected independently from the group consisting of a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and an adjacent group having 6 to 30 carbon atoms,
The R is 1 To R 4 At least one of them is deuterium, and at least one of them is deuterium,
r is not deuterium 1 To R 4 Each of which is the same or different from the other and is selected from the group consisting of hydrogen, cyano, nitro, halo, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 5 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl of 6 to 30 carbon atoms, substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, and substituted or unsubstituted aryl of 7 to 30 carbon atomsAn aralkylamino group, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, capable of forming a substituted or unsubstituted ring in combination with the adjacent groups,
The L is 1 、L 2 、Ar 1 To Ar 4 R is R 1 To R 4 The substituents selected from the group consisting of hydrogen, deuterium, cyano, nitro, halo, hydroxy, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms, alkynyl of 2 to 24 carbon atoms, heteroalkyl of 2 to 30 carbon atoms, aralkyl of 7 to 30 carbon atoms, cycloalkyl of 3 to 20 carbon atoms, heterocycloalkyl of 3 to 20 carbon atoms, aryl of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms, heteroarylalkyl of 3 to 30 carbon atoms, alkoxy of 1 to 30 carbon atoms, alkylsilyl of 1 to 30 carbon atoms, arylsilyl of 6 to 30 carbon atoms and aryloxy of 6 to 30 carbon atoms are the same as or different from each other when substituted with a plurality of substituents.
In addition, the present invention provides an organic light emitting element including: a first electrode; a second electrode disposed opposite to the first electrode; and more than one organic layer arranged between the first electrode and the second electrode; and at least one of the one or more organic layers includes a compound represented by the chemical formula 1.
For example, the organic electroluminescent element may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. However, the structure of the organic electroluminescent element is not limited thereto, and may include a smaller number of organic layers.
According to a preferred embodiment of the present invention, the organic layer is a light-emitting layer, and the light-emitting layer is characterized by comprising the compound represented by the chemical formula 1.
According to a preferred embodiment of the present invention, the organic layer is a hole injection layer, a hole transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, or the electron blocking layer is characterized by including the compound represented by the chemical formula 1.
In the present specification, "halo" is fluoro, chloro, bromo or iodo.
In the present invention, "alkyl" means a monovalent substituent derived from a saturated hydrocarbon having 1 to 40 carbon atoms, which is straight or branched. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like.
In the present invention, "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), and 2-butenyl (2-butenyl), but are not limited thereto.
In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl (ethyl), 2-propynyl (2-propynyl) and the like.
In the present invention, "alkylthio" refers to the alkyl group bonded through a sulfur linkage (-S-).
In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are bonded. In addition, more than two rings may be included in either a pendant (pendant) or fused form. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthryl, anthracyl, fluorenyl, dimethylfluorenyl, and the like.
In the present invention, "heteroaryl" means a monovalent substituent derived from a mono-or polyheterocyclic aromatic hydrocarbon having 6 to 30 carbon atoms. At this time, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S or Se. In addition, more than two rings may be included in either a pendant (pendant) or fused form, and may also include fused forms with aryl groups. Examples of such heteroaryl groups include 6-membered monocyclic groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl, and polycyclic and 2-purinyl groups such as phenolthienyl (phenolthienyl), indolizinyl (indoxyl), indolyl (indoxyl), purinyl (purinyl), quinolinyl (quinolyl), benzothiazole (benzothiazole) and carbazolyl (carbazolyl), N-imidazolyl, 2-isoxazolyl, 2-pyridyl and 2-pyrimidinyl, but are not limited thereto.
In the present invention, "aryloxy" is a monovalent substituent represented by RO-and R is an aryl group having 6 to 60 carbon atoms. Examples of such an aryloxy group include, but are not limited to, phenoxy, naphthoxy, diphenoxy, and the like.
In the present invention, "alkyloxy" is a monovalent substituent represented by R' O-which refers to an alkyl group having 1 to 40 carbon atoms, and may include a straight chain (linear), branched, or cyclic (cyclic) structure. Examples of the alkyl group include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
In the present invention, "alkoxy" (alkoxy) may be straight, branched or cyclic. The number of carbon atoms of the oxygen-fired group is not particularly limited, and is preferably 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.
In the present invention, "aralkyl" means aryl and alkyl are aryl-alkyl as described above. Preferred aralkyl groups include lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenethyl, and naphthylmethyl. The linkage to the parent residue is through alkyl.
In the present invention, "arylamino group" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.
In the present invention, "alkylamino" refers to an amine substituted with an alkyl group having 1 to 30 carbon atoms.
In the present invention, "aralkylamino group" means an amine substituted with an aryl-alkyl group having 7 to 30 carbon atoms.
In the present invention, "heteroarylamino" means an amino group substituted with an aryl group having 6 to 30 carbon atoms and a heterocyclic group.
In the present invention, "heteroaralkyl" refers to an aryl-alkyl group substituted with a heterocyclic group.
In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl (norbornyl), adamantane (amantadine), and the like.
In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, and one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S or Se. Examples of such heterocycloalkyl groups include, but are not limited to, morpholine, piperazine, and the like.
In the present invention, "alkylsilyl" refers to a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" refers to a silyl group substituted with an aryl group having 6 to 60 carbon atoms.
In the present invention, "fused ring" refers to a form of a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.
In the present invention, "combine with adjacent groups to form a ring" means combine with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a fused ring thereof.
In the present specification, the term "alicyclic compound" means the same as the term "aliphatic hydrocarbon ring", and the term "non-aromatic ring" means a ring composed of only carbon and hydrogen atoms.
In the present specification, the "heteroalicyclic compound" means an alicyclic compound in which one or more carbons in the "aliphatic hydrocarbon ring" are substituted with a heteroatom, thereby containing at least one or more heteroatoms.
Examples of the "aromatic hydrocarbon ring" in the present specification include, but are not limited to, phenyl, naphthyl, anthracenyl, and the like.
In the present specification, "aliphatic heterocyclic ring" means an aliphatic ring containing one or more hetero atoms.
In the present specification, the term "aromatic heterocycle" means an aromatic ring containing one or more hetero atoms. .
In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring, and aromatic heterocyclic ring may be monocyclic or polycyclic.
In the present specification, "concentration quenching (concentration quenching)" means that the luminous efficiency of the element decreases with an increase in the concentration of the dopant molecule.
In the present specification, "boron-based element", "boron-based compound", "boron-based dopant" means boron (B) element having an atomic sequence of 5, a boron-containing compound or a dopant.
In the present specification, "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is converted by another substituent, and the substituted position is not limited as long as it is a position where the hydrogen atom is substituted, that is, a position where the substituent may be substituted, and when two or more substituents are substituted, two or more substituents are the same or different from each other. The substituent may be one or more substituents selected from the group consisting of hydrogen, deuterium, cyano, nitro, halo, hydroxy, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms, alkynyl of 2 to 24 carbon atoms, heteroalkyl of 2 to 30 carbon atoms, aralkyl of 7 to 30 carbon atoms, aryl of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms, heteroarylalkyl of 3 to 30 carbon atoms, alkoxy of 1 to 30 carbon atoms, alkylamino of 1 to 30 carbon atoms, arylamino of 6 to 30 carbon atoms, aralkylamino of 6 to 30 carbon atoms, and heteroarylamino of 2 to 24 carbon atoms, but is not limited to the examples.
Effects of the invention
The present invention relates to a novel organic compound and an organic electroluminescent element comprising the same, and provides an organic electroluminescent element having a low driving voltage and excellent lifetime characteristics by using an organic compound having excellent lifetime, efficiency and electrochemical stability, which comprises a pyrene structure substituted with deuterium.
In addition, a blue host/dopant system and an organic electroluminescent element suitable for the blue series of AM-OLEDs are provided using the organic compounds.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail to facilitate the implementation of the present invention by those skilled in the art. The invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
The present invention relates to a novel organic compound including a pyrene structure substituted with deuterium, and an organic electroluminescent element including the novel organic compound.
The novel compound having a pyrene structure as a core can be driven at a low voltage and can improve color purity. In addition, when used as a dopant material, the organic electroluminescent element can be provided with high luminous efficiency, excellent heat resistance and excellent color purity.
However, in the case of using an organic electroluminescent element, the conventional pyrene-structure-based compound was confirmed to have excellent luminous efficiency, heat resistance and color purity as described above, but it did not exhibit the desired long-life effect in terms of life.
Accordingly, the present invention provides a novel organic compound having a pyrene structure substituted with deuterium, which can provide an organic electroluminescent element having improved luminous efficiency, excellent heat resistance, excellent color purity, and a longer lifetime than conventional pyrene structure compounds.
Specifically, the compound represented by the following chemical formula 1 is as follows:
[ chemical formula 1]
Wherein,
n, m, o and p are identical or different from each other and are each independently an integer from 1 to 2,
L 1 l and L 2 Are identical or different from one another and are each independently a single bond, an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 6 to 30 carbon atoms,
Ar 1 to Ar 4 Each of which is the same or different from the other and is selected independently from the group consisting of a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, a substituted or unsubstituted heteroalkyl group having 2 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and an adjacent group having 6 to 30 carbon atoms,
The R is 1 To R 4 At least one of them is deuterium, and at least one of them is deuterium,
r is not deuterium 1 To R 4 Each of which is the same or different from the other and is independently selected from the group consisting of hydrogen, cyano, nitro, halo, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, and substituted or unsubstituted arylA heteroaryl group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, capable of being bonded to each other with the adjacent groups to form a substituted or unsubstituted ring,
The L is 1 、L 2 、Ar 1 To Ar 4 R is R 1 To R 4 The substituents selected from the group consisting of hydrogen, deuterium, cyano, nitro, halo, hydroxy, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms, alkynyl of 2 to 24 carbon atoms, heteroalkyl of 2 to 30 carbon atoms, aralkyl of 7 to 30 carbon atoms, cycloalkyl of 3 to 20 carbon atoms, heterocycloalkyl of 3 to 20 carbon atoms, aryl of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms, heteroarylalkyl of 3 to 30 carbon atoms, alkoxy of 1 to 30 carbon atoms, alkylsilyl of 1 to 30 carbon atoms, arylsilyl of 6 to 30 carbon atoms and aryloxy of 6 to 30 carbon atoms are the same as or different from each other when substituted with a plurality of substituents.
The chemical formula 1 may be a compound represented by the following chemical formula 2:
[ chemical formula 2]
Wherein,
L 1 、L 2 ar and Ar 1 To Ar 4 As defined in the claim 1 of the present application,
R 5 to R 12 At least one of them is deuterium, and at least one of them is deuterium,
r is not deuterium 5 To R 12 Each of which is the same or different from the other and is selected independently from the group consisting of hydrogen, cyano, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 5 to 60 carbon atoms, substituted or unsubstituted heteroarylalkyl of 6 to 30 carbon atoms, substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted aralkylamino of 7 to 30 carbon atoms, substituted or unsubstituted arylamino of 2 to 24 carbon atoms, substituted or unsubstituted arylamino of 1 to 30 carbon atoms, substituted or unsubstituted silyl of 1 to 30 carbon atoms and substituted or unsubstituted silyl of 6 to 30 carbon atoms which are capable of bonding to each other and form an adjacent ring,
The R is 5 To R 12 The substituents selected from the group consisting of hydrogen, deuterium, cyano, nitro, halo, hydroxy, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms, alkynyl of 2 to 24 carbon atoms, heteroalkyl of 2 to 30 carbon atoms, aralkyl of 7 to 30 carbon atoms, cycloalkyl of 3 to 20 carbon atoms, heterocycloalkyl of 3 to 20 carbon atoms, aryl of 6 to 30 carbon atoms, heteroaryl of 2 to 30 carbon atoms, heteroarylalkyl of 3 to 30 carbon atoms, alkoxy of 1 to 30 carbon atoms, alkylsilyl of 1 to 30 carbon atoms, arylsilyl of 6 to 30 carbon atoms and aryloxy of 6 to 30 carbon atoms are the same as or different from each other when substituted with a plurality of substituents.
The R is 5 To R 12 At least four of them are deuterium.
The L is 1 L and L 2 Are identical or different from one another and are each independently a single bond or an arylene group having 6 to 30 carbon atoms.
The Ar is as follows 1 To Ar 4 Identical to or different from each other, may each be independently selected from the group consisting of substituents represented by chemical formulas 3 to 9:
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
[ chemical formula 8]
[ chemical formula 9]
Wherein,
q is an integer of 0 to 4,
r is an integer of 0 to 6,
s is an integer of 0 to 3,
t is an integer of 0 to 7,
u is an integer of 0 to 3,
X 1 to X 4 、X 7 、X 8 、X 11 X is X 12 Are identical or different from each other and are each independently C (R 18 ) Or N, or a combination of two,
X 5 、X 6 、X 9 x is X 10 Are identical or different from each other and are each independently selected from the group consisting of C (R 19 )(R 20 )、N(R 21 ) A group consisting of O and S,
R 13 to R 21 Each of which is the same or different from the other and is selected independently from the group consisting of hydrogen, deuterium, cyano, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio of 1 to 4 carbon atoms, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl of 3 to 20 carbon atoms, substituted or unsubstituted alkenyl of 2 to 30 carbon atoms, substituted or unsubstituted alkynyl of 2 to 24 carbon atoms, substituted or unsubstituted aralkyl of 7 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl of 5 to 60 carbon atoms, substituted or unsubstituted alkoxy of 1 to 30 carbon atoms, substituted or unsubstituted alkylamino of 1 to 30 carbon atoms, substituted or unsubstituted arylamino of 6 to 30 carbon atoms, substituted or unsubstituted arylamino of 7 to 30 carbon atoms, substituted or unsubstituted heteroarylamino of 2 to 24 carbon atoms, substituted or unsubstituted silyl of 1 to 30 carbon atoms, and substituted or unsubstituted aryl of 1 to 30 carbon atoms can form adjacent groups with each other and form an oxygen-substituted or unsubstituted silyl of 6 to 30 carbon atoms,
The R is 13 To R 21 Is selected from the group consisting of hydrogen, deuterium, cyano, nitro, halo, hydroxy, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms, and CAlkynyl group of 2 to 24, heteroalkyl group of 2 to 30 carbon atoms, aralkyl group of 7 to 30 carbon atoms, cycloalkyl group of 3 to 20 carbon atoms, heterocycloalkyl group of 3 to 20 carbon atoms, aryl group of 6 to 30 carbon atoms, heteroaryl group of 2 to 30 carbon atoms, heteroarylalkyl group of 3 to 30 carbon atoms, alkoxy group of 1 to 30 carbon atoms, alkylsilyl group of 1 to 30 carbon atoms, arylsilyl group of 6 to 30 carbon atoms and aryloxy group of 6 to 30 carbon atoms are substituted with a plurality of substituents, and they are the same or different from each other.
The Ar is as follows 1 To Ar 4 Ar in (1) 1 Ar and Ar 3 Ar is the same substituent 2 Ar and Ar 4 Are the same substituents.
The Ar is as follows 1 To Ar 4 Characterized in that the substituents based on symmetry of the core compound consist of identical substituents.
The compound represented by the chemical formula 1 may be selected from the group consisting of:
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more specifically, the preparation method of the compound represented by the chemical formula 1 includes the steps of: step 1, deuterating a substituted or unsubstituted pyrene compound under an organic solvent, a deuterium source and a metal catalyst;
A step 2 of halogenating the deuterium-substituted pyrene compound of the step 1; a kind of electronic device with high-pressure air-conditioning system
And 3. Reacting the pyrene compound substituted with a halogen group through the halogenation reaction with an aromatic amine.
More specifically, a substituted or unsubstituted pyrene compound is reacted with an organic solvent, a deuterium source and a metal catalyst, and deuteration reaction is performed to replace hydrogen in the pyrene compound with deuterium.
The metal catalyst may be selected from the group consisting of platinum, palladium, rhodium, ruthenium, nickel, cobalt, oxides thereof, complexes thereof, and combinations thereof, and is not limited as long as it can be used for deuteration reaction.
The deuterium source is selected from heavy water (D 2 O), perdeuterated benzene (benzene-D) 6 ) Perdeuterated toluene (toluene-D) 8 ) Perdeuterated xylene (xylene-D) 10 )、CDCl 3 CD (compact disc) 3 OD, preferably heavy water (D 2 O) or perdeuterated benzene (benzene-D) 6 ) But are not limited to the examples, and are used without limitation as long as they are deuterium sources that can be selected by those skilled in the art.
The organic solvent may be selected from the group consisting of ethers, alcohols, alkanes, cycloalkanes, acids, amides, or esters, and combinations thereof, but is not limited to the examples, and is not limited as long as it is a reaction solvent that can be selected by one skilled in the art.
The halogenation reaction reacts with N-Bromosuccinimide (NBS) to replace the halogen groups, followed by a carbon-carbon bond formation reaction with an organoboron compound.
The halogenation reaction can be carried out using N-Bromosuccinimide (NBS), and is not limited to N-Bromosuccinimide (NBS) as long as it can be substituted with a halogen group, and can be used as a reaction compound.
The halogenation reaction attacks the weakest C-D to disengage D and replace it with halogen radical.
Substituted with a halogen group, and then reacted with an aromatic amine compound to form a bond between N of the aromatic amine compound and a pyrene compound.
The compound of formula 1 of the present invention can be effectively used as a Dopant (Dopant) substance of a light emitting layer. In particular, the organic compound, as a Dopant (Dopant) species, is capable of providing an organic compound that is thermally stable and minimizes concentration quenching phenomena as compared to existing boron-based dopants.
The organic compound of the present invention can be effectively used as a material for forming a light-emitting layer. The material for forming a light-emitting layer may further include, for example, a host substance or the like, that is, a substance which is generally added when the organic compound is produced into a form required for forming a light-emitting layer.
The light-emitting layer-forming material may be a Dopant (Dopant) material.
The present invention provides an organic electroluminescent element comprising the compound represented by the chemical formula 1.
The organic compound of the present invention can be effectively used as a material for forming a hole injection layer, a hole transport layer or an electron blocking layer.
The present invention also relates to a material for forming a light-emitting layer, which contains the organic compound.
The material for forming a light-emitting layer may further include, for example, a dopant substance or the like, that is, a substance which is generally added when the organic compound is manufactured into a form required for forming a light-emitting layer.
In addition, the present invention relates to an organic electroluminescent element in which an organic thin film layer composed of one or more layers including at least a light-emitting layer is laminated between a negative electrode and a positive electrode,
in the organic electroluminescent element, the light emitting layer includes one kind of organic compound represented by the chemical formula 1 alone or includes two or more kinds of organic compounds in combination.
The organic electroluminescent element may have a structure in which a positive electrode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a negative electrode are laminated, and an electron blocking layer, a hole blocking layer, and the like may be further laminated as needed.
Hereinafter, the organic electroluminescent element of the present invention will be exemplified. However, the following example content does not limit the organic electroluminescent element of the present invention.
The organic electroluminescent element of the present invention may have a structure in which a positive electrode (hole injection electrode), a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), and a negative electrode (electron injection electrode) are sequentially laminated, and preferably, an Electron Blocking Layer (EBL) may be further included between the positive electrode and the emission layer, and an Electron Transport Layer (ETL), an Electron Injection Layer (EIL) may be further included between the negative electrode and the emission layer. In addition, a Hole Blocking Layer (HBL) may be further included between the anode and the light emitting layer.
As a method for manufacturing the organic electroluminescent element of the present invention, first, a substance for a positive electrode is coated on a substrate surface by a conventional method to form a positive electrode. In this case, the substrate used is preferably a glass substrate or a transparent plastic substrate excellent in transparency, surface flatness, ease of handling, and water repellency. As the material for the positive electrode, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO), or the like which is transparent and has excellent conductivity, can be used 2 ) Zinc oxide (ZnO), and the like.
Next, a Hole Injection Layer (HIL) substance is vacuum thermally evaporated or spin-coated on the positive electrode surface in a conventional manner to form a hole injection layer. Examples of such a hole injection layer material include copper phthalocyanine (CuPc), 4',4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4',4" -tris (3-methylphenylamino) phenoxybenzene (m-MTDAPB), 4',4 "-tris (N-carbazolyl) triphenylamine (TCTA) which is a star burst (starburst) amine, 4',4" -tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA), and IDE406 which can be purchased from the company of light-emitting and light producing (Idemitsu).
A Hole Transport Layer (HTL) material is vacuum thermally evaporated or spin-coated on the surface of the hole injection layer in a conventional manner to form a hole transport layer. In this case, examples of the hole transporting layer material include bis (N- (1-naphthyl-N-phenyl)) benzidine (. Alpha. -NPD), N '-bis (naphthalen-1-yl) -N, N' -biphenyl-benzidine (NPB), and N, N '-biphenyl-N, N' -bis (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine (TPD).
A light emitting layer (EML) material is vacuum thermally evaporated or spin-coated on the surface of the hole transport layer in a conventional manner to form a light emitting layer. At this time, tris (8-hydroxyquinolinyl) aluminum (Alq) can be used as the light-emitting substance alone or as the light-emitting host substance in the light-emitting layer substance to be used in green 3 ) For example, an anthracene compound is preferably used in blue.
The compound of the present invention may be used as a Dopant (Dopant) that can be used together with the light-emitting host in the light-emitting layer material.
Optionally, an Electron Blocking Layer (EBL) may be further formed between the hole transport layer and the light emitting layer.
An Electron Transport Layer (ETL) material is vacuum thermally evaporated or spin-coated on the surface of the light emitting layer in a conventional manner to form an electron transport layer. In this case, the electron transport layer material to be used is not particularly limited, and tris (8-hydroxyquinolinyl) aluminum (Alq 3 )。
Alternatively, by further forming a Hole Blocking Layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent Dopant (Dopant) in the light emitting layer, a phenomenon in which triplet excitons or holes diffuse into the electron transport layer can be prevented.
The hole blocking layer can be formed by vacuum thermal evaporation or spin coating of a hole blocking layer substance by a conventional method, and the hole blocking layer substance is not particularly limited, and (8-hydroxyquinolinyl) lithium (Liq), bis (8-hydroxy-2-methylquinolinyl) -biphenoxyaluminum (BAlq), bathocuproine (BCP), liF, and the like can be preferably used.
An Electron Injection Layer (EIL) substance is vacuum thermally evaporated or spin-coated on the surface of the electron transport layer in a conventional manner to form an electron injection layer. At this time, the electron injection layer material used was LiF, liq, li 2 O, baO, naCl, csF, etc.
And vacuum thermal evaporation of a negative electrode material on the surface of the electron injection layer by a conventional method to form a negative electrode.
In this case, lithium (Li), aluminum (Al), aluminum lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium indium (Mg-In), magnesium silver (Mg-Ag), and the like can be used as the negative electrode material. In addition, the front light emitting organic electroluminescent element may use Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO) to form a transparent negative electrode capable of transmitting light.
The surface of the negative electrode may be formed with a coating layer (CPL) from the coating layer-forming composition.
The synthetic method of the compound will be described below by way of a representative example. However, the synthesis method of the compound of the present invention is not limited to the following method, and the compound of the present invention can be produced by the following method and methods known in the art.
Synthesis example
Synthesis example 2-1 Synthesis of intermediate B-1
Starting materials B (10.00 g,43.4 mmol) and Platinum oxide (IV) (0.49 g,2.2 mmol), D 2 O (200 mL), 2-Pentanol (2-Pentanol) (20 mL), decalin (decahydroaphthaene) (200 mL) were put into a autoclave, stirred at 100℃for 12 hours, and cooled to room temperature. After methylene chloride was added, layers were separated and an organic layer was obtained. With MgSO 4 Drying and filtering. After concentrating the filtrate, B-1 (8.28 g,34.7 mmol) was obtained in 80% yield and 91% deuterium conversion by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：238[M]+
Synthesis example 2-2 Synthesis of intermediate B-2
After the starting material B-1 (8.28 g,34.7 mmol) was dissolved in 83mL of methylene chloride, NBS (18.55 g,104.2 mmol) was charged and stirred at room temperature for 12 hours. By water andafter the reaction was separated from the dichloromethane, it was separated with MgSO 4 The organic layer was dried and filtered. After concentrating the filtrate, B-2 (9.31 g,23.6 mmol) was obtained in 68% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：394[M]+
Synthesis examples 2 to 3 Synthesis of Compound 2
After dissolving starting material B-2 (9.31 g,23.6 mmol) and starting material B-3 (15.79 g,59.1 mmol) in 93mL toluene, na-O was added t Bu(11.35g，118.1mmol)、Pd 2 (dba) 3 (1.08g，1.2mmol)、 t Bu 3 P (0.96 g,2.4mmol,50% toluene solution (Solution in Toluene)) and stirring under heating/refluxing for 6 hours. After confirming completion of the reaction, 100mL of water was added to extract the toluene layer, and 100mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. Thereafter, compound 2 (7.97 g,10.4 mmol) was obtained in a yield of 44% by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：767[M]+
Synthesis example 3 Synthesis of Compound 3
After dissolving starting material A-2 (5.00 g,13.6 mmol) and starting material C-3 (7.65 g,34.0 mmol) in 50mL toluene, na-O was added t Bu(6.53g，67.9mmol)、Pd 2 (dba) 3 (0.62g，0.7mmol)、 t Bu 3 P (0.55 g,1.4mmol,50% toluene solution (Solution in Toluene)) and stirring under heating/refluxing for 6 hours. After confirming completion of the reaction, 50mL of water was added to extract the toluene layer, and 50mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. Then, the column layer is utilizedThe compound 3 (5.18 g,7.9 mmol) was obtained in 58% yield by chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：656[M]+
Synthesis example 4-1 Synthesis of intermediate D-1
Starting material D (10.0 g,38.7 mmol) and Platinum oxide (IV) (0.44 g,1.9 mmol), D 2 O (200 mL), 2-Pentanol (2-Pentanol) (20 mL) and decalin (Decahydronaphthalene) (200 mL) were put into a autoclave, stirred at 100℃for 12 hours, and cooled to room temperature. After methylene chloride was added, layers were separated and an organic layer was obtained. With MgSO 4 Drying and filtering. After concentrating the filtrate, D-1 (7.73 g,29.0 mmol) was obtained in 75% yield and 81% deuterium conversion by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：266[M]+
Synthesis example 4-2 Synthesis of intermediate D-2
After dissolving the starting material D-1 (7.73 g,29.0 mmol) in 77mL of methylene chloride, NBS (15.49 g,87.0 mmol) was added and stirred at room temperature for 12 hours. After the reaction was separated by water and dichloromethane, it was separated by MgSO 4 The organic layer was dried and filtered. After concentrating the filtrate, D-2 (7.96 g,18.9 mmol) was obtained in 65% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：422[M]+
Synthesis examples 4-3 Synthesis of Compound 5
After dissolving starting material D-2 (7.96 g,18.9 mmol) and starting material D-3 (11.94 g,47.1 mmol) in 80mL tolueneAdding Na-O t Bu(9.06g，94.3mmol)、Pd 2 (dba) 3 (0.86g，0.9mmol)、 t Bu 3 P (0.76 g,1.9mmol,50% toluene solution (Solution in Toluene)) and stirred under heating/reflux for 6 hours. After confirming completion of the reaction, 80mL of water was added to extract the toluene layer, and 80mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. Thereafter, compound 5 (6.80 g,8.9 mmol) was obtained in 47% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：767[M]+
Synthesis example 5-1 Synthesis of intermediate E-1
Starting material E (10.0 g,34.9 mmol) and Platinum oxide (IV) (0.40 g,1.7 mmol), D 2 O (200 mL), 2-Pentanol (2-Pentanol) (20 mL) and decalin (Decahydronaphthalene) (200 mL) were put into a autoclave, stirred at 100℃for 12 hours, and cooled to room temperature. After methylene chloride was added, layers were separated and an organic layer was obtained. With MgSO 4 Drying and filtering. After concentrating the filtrate, E-1 (6.99 g,23.7 mmol) was obtained in 68% yield and 72% deuterium conversion by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：294[M]+
Synthesis example 5-2 Synthesis of intermediate E-2
After the starting material E-1 (6.99 g,23.7 mmol) was dissolved in 70mL of methylene chloride, NBS (12.67 g,71.2 mmol) was charged and stirred at room temperature for 12 hours. After the reaction was separated by water and dichloromethane, it was separated by MgSO 4 The organic layer was dried and filtered. After concentrating the filtrate, E-2 (6.52 g,14.5 mmol) was obtained in 61% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：450[M]+
Synthesis examples 5 to 3 Synthesis of Compound 6
After dissolving starting material E-2 (6.52 g,14.5 mmol) and starting material E-3 (9.76 g,36.2 mmol) in 65mL toluene, na-O was added t Bu(6.96g，72.4mmol)、Pd 2 (dba) 3 (0.66g，0.7mmol)、 t Bu 3 P (0.59 g,1.4mmol,50% toluene solution (Solution in Toluene)) and stirring for 6 hours under heating/reflux. After confirming completion of the reaction, 65mL of water was added to extract the toluene layer, and 65mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. Thereafter, compound 6 (6.11 g,7.4 mmol) was obtained in a yield of 51% by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：827[M]+
Synthesis example 6-1 Synthesis of intermediate F-1
Starting material F (10.0 g,32.0 mmol) and Platinum oxide (IV) (0.36 g,1.6 mmol), D 2 O (200 mL), 2-Pentanol (2-Pentanol) (20 mL) and decalin (Decahydronaphthalene) (200 mL) were put into a autoclave, stirred at 100℃for 12 hours, and cooled to room temperature. After methylene chloride was added, layers were separated and an organic layer was obtained. With MgSO 4 Drying and filtering. After concentrating the filtrate, F-1 (5.73 g,17.9 mmol) was obtained in 56% yield and 60% deuterium conversion by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：319[M]+
Synthesis example 6-2 Synthesis of intermediate F-2
After the starting material F-1 (5.73 g,17.9 mmol) was dissolved in 57mL of methylene chloride, NBS (9.58 g,53.8 mmol) was charged and stirred at room temperature for 12 hours. After the reaction was separated by water and dichloromethane, it was separated by MgSO 4 The organic layer was dried and filtered. After concentrating the filtrate, F-2 (4.94 g,10.4 mmol) was obtained in 58% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：475[M]+
Synthesis example 6-3 Synthesis of Compound 7
After dissolving starting material F-2 (4.94 g,10.4 mmol) and starting material F-3 (6.58 g,26.0 mmol) in 50mL of toluene, na-O was added t Bu(4.99g，52.0mmol)、Pd 2 (dba) 3 (0.48g，0.5mmol)、 t Bu 3 P (0.42 g,1.0mmol,50% toluene solution (Solution in Toluene)) and stirred under heating/reflux for 6 hours. After confirming completion of the reaction, 50mL of water was added to extract the toluene layer, and 50mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. Thereafter, compound 7 (4.86 g,5.9 mmol) was obtained in 57% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：820[M]+
Synthesis example 7 Synthesis of Compound 8
After dissolving starting material A-2 (5.00G, 13.6 mmol) and starting material G-1 (8.60G, 34.0 mmol) in 50mL toluene, na-O was added t Bu(6.53g，67.9mmol)、Pd 2 (dba) 3 (0.62g，0.7mmol)、 t Bu 3 P (0.55 g,1.4mmol,50% toluene solution (Solution in Toluene)) and heating/returnThe mixture was stirred in the flow state for 6 hours. After confirming completion of the reaction, 50mL of water was added to extract the toluene layer, and 50mL of water was added to extract the toluene layer again. The extracted solution was treated with MgSO 4 Treated to remove residual moisture and dried in a vacuum oven. Thereafter, compound 8 (6.59 g,9.2 mmol) was obtained in 68% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：713[M]+
Synthesis example 8 Synthesis of Compound 10
After dissolving starting material E-2 (5.00 g,11.1 mmol) and starting material H-1 (8.37 g,27.8 mmol) in 50mL of toluene, na-O was added t Bu(5.34g，55.5mmol)、Pd 2 (dba) 3 (0.51g，0.6mmol)、 t Bu 3 P (0.45 g,1.1mmol,50% toluene solution (Solution in Toluene)) and stirred under heating/reflux for 6 hours. After confirming completion of the reaction, 50mL of water was added to extract the toluene layer, and 50mL of water was added to extract the toluene layer again. The extracted solution was treated with MgSO 4 Treated to remove residual moisture and dried in a vacuum oven. Thereafter, compound 10 (5.44 g,6.1 mmol) was obtained in 55% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：891[M]+
Synthesis example 9-1 Synthesis of intermediate I-1
Starting material I (20.00 g,118.9 mmol) and Platinum oxide (IV) (1.35 g,5.9 mmol), D 2 O (400 mL), 2-Pentanol (2-Pentanol) (40 mL) and decalin (Decahydronaphthalene) (400 mL) were put into a autoclave, stirred at 100℃for 12 hours, and cooled to room temperature. After methylene chloride was added, layers were separated and an organic layer was obtained. With MgSO 4 Drying and filtering. After concentrating the filtrate, column chromatography (dichloromethane,Heptane) to yield I-1 (15.09 g,85.6 mmol) in 72% yield and 88% deuterium conversion.
MS(MALDI-TOF)m/z：176[M]+
Synthesis example 9-2 Synthesis of intermediate I-2
After dissolving the starting material I-1 (10.00 g,58.9 mmol) in 80mL of THF, 40mL of n-butyllithium (molar concentration in hexane 1.6M) was added dropwise at-40 ℃. After that, the temperature was raised to room temperature and stirred for 2 hours. After the temperature of the reaction flask was again lowered to-78 ℃, 80mL of 1,2-Dibromoethane (16.03 g,84.5 mmol) dissolved in THF was slowly added dropwise. After stirring at low temperature for 30 minutes, the temperature was raised to normal temperature and stirred for 2 hours. Thereafter, 50mL of supersaturated solution of sodium chloride was added and the organic layer was separated. The oily mixture obtained by drying the separated organic layer by evaporation was dissolved in 100mL of methylene chloride, and after separating the organic layer by adding 50mL of 1N hydrochloric acid solution, 50mL of water was further added, and the organic layer was separated again. With MgSO 4 The separated organic layer was dried and filtered. The resulting solid was washed twice with 30mL of isopropanol and dried in vacuo to give intermediate I-2 (8.92 g,35.1 mmol) in 60% yield.
MS(MALDI-TOF)m/z：254[M]+
Synthesis example 9-3 Synthesis of intermediate I-4
After dissolving starting material I-2 (8.92 g,35.1 mmol) and starting material I-3 (5.17 g,52.7 mmol) in 90mL of toluene, na-O was added t Bu(10.12g，105.3mmol)、Pd 2 (dba) 3 (0.96g，1.1mmol)、 t Bu 3 P (0.85 g,2.1mmol,50% toluene solution (Solution in Toluene)) and stirred under heating/reflux for 6 hours. After confirming completion of the reaction, 90mL of water was added to extract the toluene layer, and 90mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. Thereafter, compound I-4 (7.05 g,26.0 mmol) was obtained in 74% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：271[M]+
Synthesis example 11 Synthesis of Compound 46
After dissolving starting material E-2 (5.00 g,11.1 mmol) and starting material J-1 (6.65 g,27.8 mmol) in 50mL of toluene, na-O was added t Bu(5.34g，55.5mmol)、Pd 2 (dba) 3 (0.51g，0.6mmol)、 t Bu 3 P (0.45 g,1.1mmol,50% toluene solution (Solution in Toluene)) and stirred under heating/reflux for 6 hours. After confirming completion of the reaction, 50mL of water was added to extract the toluene layer, and 50mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. Thereafter, compound 46 (4.09 g,5.3 mmol) was obtained in 48% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：767[M]+
Synthesis example 12 Synthesis of Compound 61
After dissolving starting material B-2 (5.00 g,12.7 mmol) and starting material K-1 (7.66 g,31.7 mmol) in 50mL toluene, na-O was added t Bu(6.10g，63.4mmol)、Pd 2 (dba) 3 (0.58g，0.6mmol)、 t Bu 3 P (0.51 g,1.3mmol,50% toluene solution (Solution in Toluene)) and stirring for 6 hours under heating/reflux. After confirming completion of the reaction, 50mL of water was added to extract the toluene layer, and 50mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. After that, the process is carried out,compound 61 (4.08 g,5.7 mmol) was obtained in 45% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：715[M]+
Synthesis example 13 Synthesis of Compound 67
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After dissolving starting material B-2 (5.00 g,12.7 mmol) and starting material L-1 (7.40 g,31.7 mmol) in 50mL of toluene, na-O was added t Bu(6.10g，63.4mmol)、Pd 2 (dba) 3 (0.58g，0.6mmol)、 t Bu 3 P (0.51 g,1.3mmol,50% toluene solution (Solution in Toluene)) and stirring for 6 hours under heating/reflux. After confirming completion of the reaction, 50mL of water was added to extract the toluene layer, and 50mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. After that, compound 67 (2.39 g,3.4 mmol) was obtained in 27% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：698[M]+
Synthesis example 14 Synthesis of Compound 101
After dissolving starting material B-2 (5.00 g,12.7 mmol) and starting material M-1 (6.99 g,31.7 mmol) in 50mL of toluene, na-O was added t Bu(6.10g，63.4mmol)、Pd 2 (dba) 3 (0.58g，0.6mmol)、 t Bu 3 P (0.51 g,1.3mmol,50% toluene solution (Solution in Toluene)) and stirring for 6 hours under heating/reflux. After confirming completion of the reaction, 50mL of water was added to extract the toluene layer, and 50mL of water was added to extract the toluene layer again. With MgSO 4 The extracted solution was treated to remove residual moisture and dried in a vacuum oven. After that, compound 101 (3.33 g,4.9 mmol) was obtained in 39% yield by column chromatography (dichloromethane, heptane).
MS(MALDI-TOF)m/z：672[M]+
Examples
< method for manufacturing organic electroluminescent element having front light-emitting Structure >
Dividing a substrate sequentially laminated with Ag as a light reflecting layer and ITO (10 nm) as a positive electrode of an organic electroluminescent element into negative and positive electrode regions and an insulating layer by photolithography (photolithography) and patterning (patterning), and then, for improving work-function and cleaning of the positive electrode (ITO), using O 2 :N 2 The plasma is surface treated. Above it to 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN) was formed as a Hole Injection Layer (HIL).
Next, N4 '-tetrakis ([ 1,1' -biphenyl) is vacuum-deposited on top of the hole injection layer]-4-yl) - [1,1' -biphenyl]-4,4' -diamine formation thickness ofIs provided. The upper part of the Hole Transport Layer (HTL) is formed as an Electron Blocking Layer (EBL)>Thickness of N-phenyl-N- (4- (spiro [ benzo [ de ])]Anthracene-7, 9' -fluorene]-2' -yl) phenyl) dibenzo [ b, d]Furan-4-amine, vapor-depositing compound alpha-beta AND as a host of the light-emitting layer on top of the Electron Blocking Layer (EBL), AND at the same time, doping compound 1 as a dopant at a concentration of 3% to form +. >A light emitting layer (EML) of thickness.
Vapor deposition of 2- (4- (9, 10-di (naphthalen-2-yl) anthracene-2-yl) phenyl) -1-phenyl-1H is carried out simultaneously at the upper part of the luminous layer in a ratio of 1:1Benzo [ d ]]Imidazole and Liq toAn Electron Transport Layer (ETL) is formed as the thickness of the electron injection layer by vapor deposition +.>Is used as a negative electrode, and the vapor deposition thickness is +.>Magnesium (Mg) and silver (Ag) in a ratio of 1:9. On the negative electrode, a coating layer is deposited to a thickness +.>N4, N4' -diphenyl-N4, N4' -bis (4- (9-phenyl-9H-carbazol-3-yl) phenyl) - [1,1' -biphenyl)]-4,4' -diamine. Protection of organic electroluminescent elements from atmospheric O by bonding a seal cap (seal cap) with a UV-curable adhesive on a cover layer (CPL) 2 Or the influence of moisture, thereby producing an organic electroluminescent element.
Examples 2 to 14: fabrication of organic electroluminescent device
An organic electroluminescent element was fabricated in the same manner as in example 1, except that compounds 1 to 3, 5 to 8, 10, 15, 16, 46, 61, 67, 101 were used instead of the compound 1 as a dopant.
Comparative examples 1 to 4: fabrication of organic electroluminescent device
An organic electroluminescent element was fabricated in the same manner as in example 1, except that compounds a to D were used instead of the compound 1 as a dopant.
Experimental example: analysis of characteristics of organic electroluminescent element
The organic electroluminescent elements produced in examples 1 to 14 and comparative examples 1 to 4 were subjected to 10mA/cm 2 Current toMeasuring electro-optical properties, applying 20mA/cm 2 The lifetime was measured by the constant current of (2), and the results are shown in table 1 below.
TABLE 1
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According to the experimental results, when the compounds of examples of the present invention are used, organic electroluminescent elements having low driving voltage, excellent lifetime and other characteristics can be provided by using organic compounds having excellent lifetime, efficiency and electrochemical stability, as compared with comparative examples 1 to 4.
While the preferred embodiments of the present invention have been described in detail, the scope of the claims of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concepts of the present invention as defined in the claims are within the scope of the claims.

Claims (7)

1. A compound represented by the following chemical formula 2:
[ chemical formula 2]
Wherein,
L 1 l and L 2 Is a single bond,
Ar 1 to Ar 4 Ar in (1) 1 Ar and Ar 3 Ar is the same substituent 2 Ar and Ar 4 Is the same substituent and Ar is 1 To Ar 4 Selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms,
R 5 To R 12 At least four of them are deuterium, and at least four of them are deuterium,
r is not deuterium 5 To R 12 Are identical to or different from each other, are each independently selected from substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms and are capable of forming a substituted or unsubstituted ring in combination with adjacent groups,
the R is 5 To R 12 Is substituted with an alkyl group having 1 to 30 carbon atoms, and when substituted with a plurality of substituents, they are the same or different from each other,
the Ar is as follows 1 To Ar 4 The substituent of (a) is selected from the group consisting of hydrogen, cyano, nitro, halogen, hydroxy, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 24 carbon atoms, heteroalkyl having 2 to 30 carbon atoms, aralkyl having 7 to 30 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heterocycloalkyl having 3 to 20 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroarylalkyl having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, alkylsilyl having 1 to 30 carbon atoms, arylsilyl having 6 to 30 carbon atoms and aryloxy having 6 to 30 carbon atoms, and when substituted with a plurality of substituents, they are the same as or different from each other.
2. The compound according to claim 1, wherein,
the Ar is as follows 1 To Ar 4 Selected from the group consisting of substituents represented by chemical formulas 3 to 9:
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
[ chemical formula 8]
[ chemical formula 9]
Wherein,
* Indicating the position of the bond(s),
q is an integer of 0 to 4,
r is an integer of 0 to 6,
s is an integer of 0 to 3,
t is an integer of 0 to 7,
u is an integer of 0 to 3,
X 1 to X 4 、X 7 、X 8 、X 11 X is X 12 Are identical or different from each other and are each independently C (R 18 ) Or N, or a combination of two,
X 5 、X 6 、X 9 x is X 10 Are identical or different from each other and are each independently selected from the group consisting of C (R 19 )(R 20 )、N(R 21 ) A group consisting of O and S,
the R is 13 To R 21 Are the same as or different from each other and are each independently selected from hydrogen, cyano, nitro, halo, hydroxyA group, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a heteroalkyl group having 2 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 3 to 20 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a heteroarylalkyl group having 3 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an alkylsilyl group having 1 to 30 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.
3. The compound according to claim 1, wherein,
The compound represented by the chemical formula 2 may be selected from the group consisting of:
4. an organic electroluminescent element, wherein,
comprising the following steps:
the first electrode is arranged to be electrically connected to the first electrode,
a second electrode disposed opposite to the first electrode, an
More than one organic layer arranged between the first electrode and the second electrode;
of the one or more organic layers, at least one includes the compound according to claim 1.
5. The organic electroluminescent element according to claim 4, wherein,
the organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
6. The organic electroluminescent element according to claim 5, wherein,
the organic layer is a light emitting layer.
7. The organic electroluminescent element according to claim 6, wherein,
the organic layer is a hole injection layer, a hole transport layer, or an electron blocking layer.
CN201911079765.8A 2018-11-07 2019-11-07 Organic compound and organic electroluminescent element comprising same Active CN111153811B (en)

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