阅读说明：本技术 芘醌类有机化合物及其应用 (Pyrene quinone organic compound and application thereof ) 是由 潘君友 宋鑫龙 杨曦 李燕妹 谭甲辉 李们在 李先杰 王煦 张月 于 2019-10-29 设计创作，主要内容包括：本发明涉及一种如通式(I)所示的芘醌类有机化合物及其应用。所述芘醌类有机化合物,具有优异的空穴传输性质及稳定性,可作为有机电致发光元件中的空穴注入层材料,也可以作为掺杂剂掺杂在空穴注入层或空穴传输层中,这样既可用低电压驱动,也可提高电致发光效率,延长器件寿命。<Image he="400" wi="446" file="DDA0002251527940000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>(The invention relates to a pyrene quinone organic compound shown as a general formula (I) and application thereof. The pyrenequinone organic compound has excellent hole transport property and stability, can be used as a hole injection layer material in an organic electroluminescent element, and can also be doped in a hole injection layer or a hole transport layer as a dopant, so that the pyrenequinone organic compound can be driven by low voltage, the electroluminescent efficiency can be improved, and the service life of a device can be prolonged.)

1. A pyrenequinone organic compound represented by the general formula (I):

wherein the content of the first and second substances,

x is independently selected from CR at each occurrence¹,N,CR¹R²,NR¹,C＝O,C＝NR¹,C＝CR¹R²,C＝Ar²,SiR¹R²,PR¹O, S or SO₂And at least one X is selected from the group consisting of C ═ O, C ═ NR¹,SO₂,C＝CR¹R²Or C ═ Ar²；

Y is selected from C or N or P;

R¹-R²each occurrence of the compound is independently selected from H, D, straight-chain alkyl, alkoxy or thioalkoxy with 1-20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy, silyl with 3-20 carbon atoms, or substituted ketone with 1-20 carbon atoms, or alkoxycarbonyl with 2-20 carbon atoms, or aryloxycarbonyl with 7-20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, nitroso, CF₃Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 carbon atoms, or an aryloxy or heteroaryloxy group having 5 to 40 carbon atoms, or a combination thereof, two or more adjacent R¹And/or two or more adjacent R²Can optionally form aliphatic, aromatic or heteroaromatic ring systems with one another;

Ar⁰，Ar¹，Ar²each occurrence is independently selected from a substituted or unsubstituted aromatic, heteroaromatic, aryloxy, heteroaryloxy group or a non-aromatic ring system of 4 to 40 ring atoms, or a combination of such groups, wherein one or more of the groups form a mono-or polycyclic aliphatic or aromatic ring system with each other and/or the rings to which the groups are bonded.

2. The pyrenequinone organic compound according to claim 1, wherein: at least one X is selected from one of G1-G19:

e is independently selected from CR at each occurrence³R⁴,NR³O, S or SO₂；

Each occurrence of Y is independently selected from CR³,N,SiR³Or P;

R³-R⁴each occurrence of the compound is independently selected from H, D, straight-chain alkyl, alkoxy or thioalkoxy with 1-20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy, silyl with 3-20 carbon atoms, or substituted ketone with 1-20 carbon atoms, or alkoxycarbonyl with 2-20 carbon atoms, or aryloxycarbonyl with 7-20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, nitroso, CF₃Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 carbon atoms, or an aryloxy group having 5 to 40 carbon atoms orHeteroaryloxy, or combinations of these, two or more adjacent R¹And/or two or more adjacent R²Optionally form aliphatic, aromatic or heteroaromatic ring systems with one another.

3. The pyrenequinone organic compound according to claim 1, wherein: at least two X are selected from C ═ NR¹Or C ═ CR¹R²。

4. The pyrenequinone organic compound according to claim 3, wherein: c ═ NR¹And C ═ CR¹R²Are respectively selected from one of the following groups:

5. the pyrenequinone organic compound according to claim 1, wherein: ar is⁰And Ar¹Each independently contains the following groups:

wherein:

X₁each occurrence is independently selected from N or CR⁵；

Y₁Each occurrence is independently selected from NR⁵,PR⁵,AsR⁵,CR⁵R⁶,SiR⁵R⁶O or S;

R⁵-R⁶each occurrence of the substituent is independently selected from H, D, straight-chain alkyl, alkoxy or thioalkoxy with 1-20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy, silyl with 3-20 carbon atoms, or substituted keto with 1-20 carbon atoms, or alkoxycarbonyl with 2-20 carbon atoms, or aryloxycarbonyl with 7-20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyanoIsocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, nitroso, CF₃Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aryl or heteroaryl group having 5 to 40 carbon atoms, or an aryloxy or heteroaryloxy group having 5 to 40 carbon atoms, or a combination thereof, two or more adjacent R³Optionally form aliphatic, aromatic or heteroaromatic ring systems with one another.

6. The pyrenequinone organic compound according to claim 5, wherein: ar is⁰And Ar¹Each independently contains the following groups:

7. the pyrenequinone organic compound according to claim 1, wherein: the general formula (I) is selected from any one of general formulas (2-1) to (2-4):

8. the pyrenequinone organic compound according to claim 7, wherein: the general formula (I) is selected from any one of general formulas (3-1) to (3-8):

wherein:

Ar³,Ar⁴each occurrence is independently selected from substituted or unsubstituted aromatic group, heteroaromatic group, aryloxy group, heteroaryloxy group or non-aromatic ring system with 4-40 ring atomsOr combinations of these groups, wherein one or more of the groups form a mono-or polycyclic aliphatic or aromatic ring system with each other and/or with the rings to which said groups are bonded.

9. A mixture comprising at least one acenaphthenequinone organic compound according to any one of claims 1 to 8, and at least one further organic functional material selected from a hole injection material, a hole transport material, an electron injection material, an electron blocking material, a hole blocking material, a light emitting material, a host material or an organic dye.

10. A composition comprising the pyrene quinone-based organic compound according to any one of claims 1 to 8, and at least one organic solvent.

11. An organic electronic device comprising the pyrene quinone based organic compound according to any one of claims 1 to 8 or the mixture according to claim 9.

Technical Field

The invention relates to the technical field of organic electroluminescence, in particular to a pyrene quinone organic compound and application thereof.

Background

Organic Light Emitting Diodes (OLEDs) have great potential for applications in optoelectronic devices, such as flat panel displays and lighting, due to their advantages of being versatile, low cost to manufacture, and good in optical and electrical performance.

The organic light emitting diode consists of three parts, namely an anode, a cathode and an organic layer between the anode and the cathode. In order to improve the efficiency and lifetime of the organic light emitting diode, the organic layer generally has a multi-layer structure, and each layer contains different organic substances. Specifically, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like may be included. The basic principle of the light emission of the organic light emitting diode is as follows: when a voltage is applied between the two electrodes, the positive electrode injects holes into the organic layer, the negative electrode injects electrons into the organic layer, and the injected holes and electrons meet to form excitons, which emit light when they transition back to the ground state. The organic light emitting diode has the advantages of self-luminescence, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, high responsiveness and the like. In order to improve the recombination efficiency of the injected holes and electrons, further improvement in the structure, material, and the like of the organic light emitting diode is required.

Therefore, scientists have utilized aromatic diamine derivatives (patent US4720432) or aromatic condensed ring diamine derivatives (patent US5061569) as hole transport materials of organic light emitting diodes to improve the efficiency of hole injection, but this time the use voltage needs to be increased to make the organic light emitting diodes emit light sufficiently, which leads to the problems of reduced lifetime and increased power consumption of the organic light emitting diodes.

The doping of electron acceptors in the hole transport layer of organic light emitting diodes is a new approach to solve such problems, such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4TCNQ) (appl. Phys. Lett., 73(22), 3202-4 (1998), appl. Phys. Lett., 73(6), 729-731(1998), however, these compounds have drawbacks when used in doping organic layers, such as unstable operation in the fabrication process of organic light emitting diodes, insufficient stability when driving organic light emitting diodes, reduced lifetime, or diffusion within the device and contamination of the device when manufacturing organic light emitting diodes by vacuum evaporation.

Currently, there is still a need for further improvement of electron acceptors, i.e., P-dopant dopants, doped in the hole transport layer, and particularly for a dopant that can achieve low voltage and long lifetime of the organic light emitting diode.

Disclosure of Invention

In view of the defects of the prior art, the invention aims to provide a pyrene quinone organic compound and application thereof.

The technical scheme of the invention is as follows:

a pyrenequinone organic compound represented by the general formula (I):

wherein the content of the first and second substances,

x is independently selected from CR at each occurrence¹,N,CR¹R²,NR¹,C＝O,C＝NR¹,C＝CR¹R²,C＝Ar²,SiR¹R²,PR¹O, S or SO₂And at least one X is selected from the group consisting of C ═ O, C ═ NR¹,SO₂,C＝CR¹R²Or C ═ Ar²；

Y is selected from C or N or P;

R¹-R²each occurrence ofEach independently selected from H, D, C1-20 linear alkyl, alkoxy or thioalkoxy, or C3-20 branched or cyclic alkyl, alkoxy, thioalkoxy, silyl, or substituted C1-20 keto, or C2-20 alkoxycarbonyl, or C7-20 aryloxycarbonyl, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanato, thiocyanate, isothiocyanate, hydroxyl, nitro, nitroso, CF, and isocyanato₃Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 carbon atoms, or an aryloxy or heteroaryloxy group having 5 to 40 carbon atoms, or a combination thereof, two or more adjacent R¹And/or two or more adjacent R²Can optionally form aliphatic, aromatic or heteroaromatic ring systems with one another;

Ar⁰，Ar¹，Ar²each occurrence is independently selected from a substituted or unsubstituted aromatic, heteroaromatic, aryloxy, heteroaryloxy group or a non-aromatic ring system of 4 to 40 ring atoms, or a combination of such groups, wherein one or more of the groups form a mono-or polycyclic aliphatic or aromatic ring system with each other and/or the rings to which the groups are bonded.

A mixture comprises at least one acenaphthoquinone organic compound and at least one other organic functional material, wherein the at least one other organic functional material can be selected from a hole injection material, a hole transport material, an electron injection material, an electron blocking material, a hole blocking material, a luminescent material, a main body material or an organic dye.

The composition comprises the pyrenequinone organic compound and at least one organic solvent.

An organic electronic device comprising the above pyrene quinone based organic compound, or the mixture thereof, or the composition thereof.

Compared with the prior art, the invention has the following beneficial effects:

the pyrenequinone organic compound has excellent hole transport property and stability, can be used as a hole injection layer material in an organic electroluminescent element, and can also be doped in a hole injection layer or a hole transport layer as a dopant, so that the pyrenequinone organic compound can be driven by low voltage, the electroluminescent efficiency can be improved, and the service life of a device can be prolonged.

Drawings

Fig. 1 is a structural view of a light emitting device of the present invention, in which 101 is a substrate, 102 is an anode, 103 is a Hole Injection Layer (HIL), 104 is a Hole Transport Layer (HTL), 105 is a light emitting layer, 106 is an Electron Injection Layer (EIL) or an Electron Transport Layer (ETL), and 107 is a cathode.

Detailed Description

To facilitate an understanding of the invention, the invention will now be described more fully with reference to the accompanying drawings. Preferred embodiments of the present invention are shown in the drawings. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.

Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.

In the compounds of the invention, when any variable (e.g. R)¹、R²Etc.) occur more than one time in any constituent, then the definition of each occurrence is independent of the definition of each other occurrence. Also, combinations of substituents and variables are permissible only if such combinations result in stable compounds.

In the present invention, the Host material, the Matrix material, the Host material and the Matrix material have the same meaning and may be interchanged.

In the present invention, the metal-organic complex, and the organometallic complex have the same meanings and may be interchanged.

In the present invention, the composition, printing ink, and ink have the same meaning and may be interchanged.

A pyrenequinone organic compound represented by the general formula (I):

wherein the content of the first and second substances,

x is independently selected from CR at each occurrence¹,N,CR¹R²,NR¹,C＝O,C＝NR¹,C＝CR¹R²,C＝Ar²,SiR¹R²,PR¹O, S or SO₂And at least one X is selected from the group consisting of C ═ O, C ═ NR¹,SO₂,C＝CR¹R²Or C ═ Ar²；

Y is selected from C or N or P; preferably, Y is selected from C;

R¹-R²each occurrence of the compound is independently selected from H, D, straight-chain alkyl, alkoxy or thioalkoxy with 1-20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy, silyl with 3-20 carbon atoms, or substituted ketone with 1-20 carbon atoms, or alkoxycarbonyl with 2-20 carbon atoms, or aryloxycarbonyl with 7-20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, nitroso, CF₃Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 40 carbon atoms, or an aryloxy or heteroaryloxy group having 5 to 40 carbon atoms, or a combination thereof, two or more adjacent R¹And/or two or more adjacent R²Can optionally form aliphatic, aromatic or heteroaromatic ring systems with one another;

Ar⁰，Ar¹，Ar²each occurrence of the substituent is independently selected from substituted or unsubstituted aromatic group, heteroaromatic group, aryloxy group with 4-40 ring atoms,Heteroaryloxy groups or non-aromatic ring systems, or combinations of such groups, wherein one or more of the groups form a mono-or polycyclic aliphatic or aromatic ring system with each other and/or the rings to which said groups are bonded.

Preferably, at least one X is selected from one of G1-G19:

wherein:

e is independently selected from CR at each occurrence³R⁴,NR³O, S or SO₂；

Each occurrence of Y is independently selected from CR³,N,SiR³Or P;

R³-R⁴each occurrence of the compound is independently selected from H, D, straight-chain alkyl, alkoxy or thioalkoxy with 1-20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy, silyl with 3-20 carbon atoms, or substituted ketone with 1-20 carbon atoms, or alkoxycarbonyl with 2-20 carbon atoms, or aryloxycarbonyl with 7-20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, nitroso, CF₃Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aryl or heteroaryl group having 5 to 40 carbon atoms, or an aryloxy or heteroaryloxy group having 5 to 40 carbon atoms, or a combination thereof, two or more adjacent R¹And/or two or more adjacent R²Optionally form aliphatic, aromatic or heteroaromatic ring systems with one another.

Further, R³-R⁴Each occurrence is independently selected from D, C1-10 linear alkyl, alkoxy or thioalkoxy, or C3-10 branched or cyclic alkyl, alkoxy, thioalkoxy, silyl, or substituted C1-10 keto, or C2-10 alkoxycarbonyl, or C7-10 aryloxycarbonyl, or cyano, carbamoylHaloformyl, formyl, isocyano, isocyanato, thiocyanate, isothiocyanato, hydroxy, nitro, nitroso, CF₃Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aryl or heteroaryl group having 5 to 20 carbon atoms, or an aryloxy or heteroaryloxy group having 5 to 20 carbon atoms, or a combination thereof, two or more adjacent R¹And/or two or more adjacent R²Optionally form aliphatic, aromatic or heteroaromatic ring systems with one another.

In one embodiment, at least 2X are selected from C ═ O, C ═ NR¹,SO₂,C＝CR¹R²Or C ═ Ar²(ii) a Preferably, at least 2X are selected from G1-G19.

In one embodiment, at least 1X is selected from C ═ NR¹,C＝CR¹R²Or C ═ Ar²(ii) a Preferably, at least 1X is selected from C ═ NR¹Or C ═ CR¹R²。

In one embodiment, at least 2X are selected from C ═ NR¹,C＝CR¹R²Or C ═ Ar²(ii) a Preferably, at least 2X are selected from C ═ NR¹Or C ═ CR¹R²。

In a certain preferred embodiment, R¹-R²When present multiple times, at least one is selected from nitro, nitroso, CF₃Cl, Br, F, I, cyano, or by nitro, nitroso, CF₃Cl, Br, F, I, cyano-substituted aryl or heteroaryl. In a certain preferred embodiment, R¹-R²When occurring for many times, all are selected from nitro, nitroso and CF₃Cl, Br, F, I, cyano, or by nitro, nitroso, CF₃Cl, Br, F, I, cyano-substituted aryl or heteroaryl.

In a certain preferred embodiment, R¹-R²When present, at least one is selected from linear or branched alkyl.

In a certain preferred embodiment, R¹-R²At least one, when present multiple times, is selected from aryl or heteroaryl; more preferably, it is selected from benzene,Naphthalene, phenanthrene, spiro, triazine, triphenylene, carbazole, furan, and derivatives thereof.

Specifically, C ═ NR¹And C ═ CR¹R²Are respectively selected from one of the following groups:

specifically, C ═ Ar²Selected from the following groups:

further, Ar⁰-Ar¹Each occurrence is independently selected from a substituted or unsubstituted aromatic, heteroaromatic, aryloxy or heteroaryloxy group of 5 to 30 ring atoms or a non-aromatic ring system, or a combination of such groups, wherein one or more of the groups form a mono-or polycyclic aliphatic or aromatic ring system with each other and/or the rings to which the groups are bonded.

Further, Ar⁰-Ar¹Each occurrence is independently selected from a substituted or unsubstituted aromatic, heteroaromatic, aryloxy or heteroaryloxy group of 5 to 15 ring atoms or a non-aromatic ring system, or a combination of such groups, wherein one or more of the groups form a mono-or polycyclic aliphatic or aromatic ring system with each other and/or the rings to which the groups are bonded.

In some preferred embodiments, the Ar is⁰And Ar¹Each independently contains the following groups:

wherein:

X₁each occurrence is independently selected from N or CR⁵；

Y₁Each occurrence is independently selected from NR⁵,PR⁵,AsR⁵,CR⁵R⁶,SiR⁵R⁶O or S;

R⁵-R⁶each occurrence of the compound is independently selected from H, D, straight-chain alkyl, alkoxy or thioalkoxy with 1-20 carbon atoms, or branched or cyclic alkyl, alkoxy, thioalkoxy, silyl with 3-20 carbon atoms, or substituted ketone with 1-20 carbon atoms, or alkoxycarbonyl with 2-20 carbon atoms, or aryloxycarbonyl with 7-20 carbon atoms, or cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, nitroso, CF₃Cl, Br, F, I, a crosslinkable group, or a substituted or unsubstituted aryl or heteroaryl group having 5 to 40 carbon atoms, or an aryloxy or heteroaryloxy group having 5 to 40 carbon atoms, or a combination thereof, two or more adjacent R³Optionally form aliphatic, aromatic or heteroaromatic ring systems with one another.

Further, said Ar⁰And Ar¹Each independently contains the following groups:

further, said Ar⁰-Ar¹Each occurrence is independently selected from benzene, biphenyl, naphthalene, anthracene, phenanthrene, triphenylene, pyrene, perylene, pyridine, pyrimidine, triazine, fluorene, dibenzothiophene, silafluorene, carbazole, thiophene, furan, thiazole, triphenylamine, triphenylphosphoroxide, tetraphenyl silicon, spirofluorene, spirosilafluorene, pyrazine, oxadiazole and derivatives thereof.

Further, said Ar⁰-Ar¹Each occurrence is partial or total hydrogenation, or, partial or total cyanation, or, partial or total halogenation, respectively.

Further, said Ar⁰-Ar¹Each occurrence is independently selected from dicyanopyridinyl, dicyanopyrazinyl, dicyanophenyl, dicyanopyrimidine, dicyanonaphthyl, or dicyanoanthracenyl.

In a certain preferred embodiment, R⁵-R⁶When the reaction solution is used for a plurality of times,at least one selected from nitro, nitroso, CF₃Cl, Br, F, I, cyano, or by nitro, nitroso, CF₃Cl, Br, F, I, cyano-substituted aryl or heteroaryl.

In a certain preferred embodiment, R⁵-R⁶When present, at least one is selected from linear or branched alkyl.

In a certain preferred embodiment, R⁵-R⁶At least one, when present multiple times, is selected from aryl or heteroaryl; more preferably, it is selected from benzene, naphthalene, phenanthrene, spiro, triazine, triphenylene, carbazole, furan and derivatives thereof.

In a preferred embodiment, the general formula (I) is selected from any one of general formulas (2-1) to (2-4):

further, the general formula (I) is selected from any one of general formulas (3-1) to (3-8):

wherein:

Ar³,Ar⁴each occurrence is independently selected from a substituted or unsubstituted aromatic, heteroaromatic, aryloxy, heteroaryloxy group or a non-aromatic ring system of 4 to 40 ring atoms, or a combination of such groups, wherein one or more of the groups form a mono-or polycyclic aliphatic or aromatic ring system with each other and/or the rings to which the groups are bonded.

Preferably, R in the above formula¹、R⁵-R⁶When present multiple times, at least one is selected from nitro, nitroso, CF₃Cl, Br, F, I, cyano, or by nitro, nitroso, CF₃Cl, Br, F, I, cyano-substituted aryl or heteroaryl. Preferably, R in the above formula¹、R⁵-R⁶At least 2, when present, being selected from nitro, nitroso, CF₃，Cl，Br, F, I, cyano, or by nitro, nitroso, CF₃Cl, Br, F, I, cyano-substituted aryl or heteroaryl. Preferably, R in the above formula¹、R⁵-R⁶When occurring for many times, all are selected from nitro, nitroso and CF₃Cl, Br, F, I, cyano, or by nitro, nitroso, CF₃Cl, Br, F, I, cyano-substituted aryl or heteroaryl.

Preferably, Ar in the above formula³,Ar⁴Each occurrence independently contains the following groups:

wherein: x₁，Y₁The meaning is the same as above.

As can be understood, the LUMO energy level of the pyrenequinone organic compound is lower than-5.3 eV; more preferably, the LUMO level is below-5.4 eV; more preferably, the LUMO level is below-5.5 eV.

In the present invention, "aromatic group" means a hydrocarbon group containing at least one aromatic ring, and includes monocyclic groups and polycyclic ring systems. "heteroaromatic group" refers to a hydrocarbon group (containing heteroatoms) containing at least one aromatic heterocyclic ring, including monocyclic groups and polycyclic ring systems. These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. At least one of these rings of the polycyclic ring system is aromatic or heteroaromatic. For the purposes of the present invention, aromatic or heteroaromatic ring systems include not only aromatic or heteroaromatic systems, but also systems in which a plurality of aromatic or heteroaromatic groups may also be interrupted by short nonaromatic units (e.g.C, N, O, Si, S or P atoms). Thus, for example, systems such as 9, 9' -spirobifluorene, 9, 9-diarylfluorene, triarylamines, diaryl ethers, etc., are likewise considered aromatic ring systems for the purposes of the present invention.

Specifically, examples of the aromatic group are: benzene, naphthalene, anthracene, phenanthrene, perylene, tetracene, pyrene, benzopyrene, triphenylene, acenaphthene, fluorene, and derivatives thereof.

Specifically, examples of heteroaromatic groups are: furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, phthalazine, quinoxaline, phenanthridine, primadine, quinazoline, quinazolinone, and derivatives thereof.

The structures of the organic compounds in some embodiments are shown below, but are not limited thereto:

the invention also relates to the composition as an organic ferromagnetic material, wherein the ferromagnetic organic compound is an organic material with ferromagnetism, also called an organic ferromagnetic material, the traditional ferromagnetic materials are inorganic materials such as alloys and oxides containing iron group or rare earth group metal elements, the ferromagnetism of the traditional ferromagnetic materials is derived from atomic magnetic moments and consists of two parts of electron orbit magnetic moments and electron spin magnetic moments, and the inorganic magnetic materials have the defects of large density, difficult processing and forming and the like, in the free radical anion salt or the di-anion salt of the pyrenequinone organic compound, the LUMO energy level is low, the ground state is stable, and a stable unfilled electron layer exists, so that a stable magnetic moment source can be provided, and the pyrenequinone organic compound is expressed as magnetism and can be applied to the ferromagnetic materials (particularly, refer to documents Angew.

Examples of organic ferromagnetic materials are listed below:

[M Cp₂ ^*]ⁿ⁺[DPQ-k]^m-,[M]ⁿ⁺[DPQ-k]^m-,[M TPP]ⁿ⁺[DPQ-k]^m-,[M₁M₂]ⁿ⁺[DPQ-k]^m-

m is a metal having an atomic weight greater than 40; m₁Is a metal having an atomic weight greater than 40; m₂Is a metal having an atomic weight greater than 40; cp₂ ^*Is dicyclopentadienyl; TPP is triphenylphosphine; m, n are integers having values from 1 to the maximum coordination number of the metal.

DPQ-k is the structure of the organic compound in the above examples, and k is the number.

In some preferred embodiments, the organic ferromagnetic material is selected from [ Fe ]^IIICp₂ ^*]⁺[DPQ-1]^-,[Cr^IIICp₂ ^*]⁺[DPQ-1]^-,[Mn TPP]⁺[DPQ-1]^-,[V]⁺[DPQ-1]^-,[Fe^IIICp₂ ^*]⁺[DPQ-2]^-,[Cr^IIICp₂ ^*]⁺[DPQ-2]^-,[Mn TPP]⁺[DPQ-2]^-,[V]⁺[DPQ-2]^-。

The organic compounds according to the invention can be used as functional materials in functional layers of electronic devices. The organic functional layer includes, but is not limited to, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), and an emission layer.

In a particularly preferred embodiment, the pyrene quinone based organic compound according to the invention is used in a Hole Injection Layer (HIL) or a Hole Transport Layer (HTL).

In a very preferred embodiment, the pyrene quinone based organic compound according to the present invention is used as a p-type dopant material in a Hole Injection Layer (HIL) or a Hole Transport Layer (HTL).

In certain embodiments, the organic compound according to the invention, T thereof₁More preferably, it is not less than 0.5eV, still more preferably not less than 0.65eV, particularly preferably not less than 0.7 eV.

Functional materials require good thermal stability. In general, the pyrene quinone organic compounds according to the present invention have a glass transition temperature Tg of 100 deg.C or higher, in a preferred embodiment 120 deg.C or higher, in a more preferred embodiment 140 deg.C or higher, in a more preferred embodiment 160 deg.C or higher, and in a most preferred embodiment 180 deg.C or higher.

In certain preferred embodiments, the pyrene quinone-based organic compound according to the invention ((HOMO- (HOMO-1)) is ≧ 0.2eV, preferably ≧ 0.25eV, more preferably ≧ 0.3eV, more preferably ≧ 0.35eV, still more preferably ≧ 0.4eV, and most preferably ≧ 0.45 eV.

The invention also provides a mixture, which is characterized by comprising at least one pyrene quinone organic compound and at least another organic functional material, wherein the at least another organic functional material can be selected from a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), a luminescent material (Emitter), a main body material (Host) and an organic dye. Various organic functional materials are described in detail, for example, in WO2010135519a1, US20090134784a1 and WO2011110277a1, the entire contents of this 3 patent document being hereby incorporated by reference.

In some preferred embodiments, the mixture, wherein the another organic functional material is selected from a Hole Injection Material (HIM), a Hole Transport Material (HTM), and a Host material (Host).

In certain preferred embodiments, the mixture wherein the LUMO of the organic compound is equal to or lower than the HOMO +0.2eV of another organic functional material.

In certain preferred embodiments, the mixture wherein the LUMO of the organic compound is equal to or lower than the HOMO +0.1eV of another organic functional material.

In certain particularly preferred embodiments, the mixture wherein the LUMO of the organic compound is equal to or lower than the HOMO of another organic functional material.

In one embodiment, the mixture includes at least one Hole Injection Material (HIM) or hole transport material and a dopant, the dopant being the above-mentioned pyrene quinone based organic compound, the molar ratio of the dopant to the host being 1:1 to 1: 100000.

Some more detailed descriptions (but not limited to) are given below for HIM/HTM/EBM, and Host (Host material).

1.HIM/HTM/EBM

Suitable organic HIM/HTM materials may be selected from compounds containing structural units selected from the group consisting of phthalocyanines, porphyrins, amines, aromatic amines, benzine triarylamines, thiophenes, benzothiophenes, pyrroles, anilines, carbazoles, azoindoazafluorenes, and derivatives thereof. In addition, suitable HIMs also include fluorocarbon containing polymers, conductively doped containing polymers, conductive polymers, such as PEDOT/PSS; self-assembling monomers, such as compounds containing phosphonic acids and sliane derivatives; metal oxides such as MoOx; metal complexes, crosslinking compounds, and the like.

The Electron Blocking Layer (EBL) serves to block electrons from adjacent functional layers, in particular the light-emitting layer. The presence of an EBL generally results in an increase in luminous efficiency compared to a light emitting device without a barrier layer. The Electron Blocking Material (EBM) of the Electron Blocking Layer (EBL) needs to have a higher LUMO than the adjacent functional layer, such as the light emitting layer. In a preferred embodiment, the EBM has a larger excited state energy level, such as singlet or triplet, depending on the emitter than the adjacent light-emitting layer, while the EBM has a hole transport function. HIM/HTM materials that generally have high LUMO levels can be used as EBMs.

Examples of cyclic aromatic amine derivative compounds that may be used as a HIM, HTM or EBM include, but are not limited to, the following general structures:

each Ar₁～Ar₉Can be independently selected from cyclic aromatic hydrocarbon compounds such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene; heteroaromatic compounds, such as dibenzothiophene, dibenzofuran, furan, thiophene, benzofuran, benzothiophene, carbazole, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, oxatriazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indolizine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, benzodiazepine, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, dibenzoselenophene, benzoselenophene, benzofuranpyridine, indolocarbazole, pyridine indole, pyrrole bipyridine, furanbipyridine, benzothiophene pyridine, thiophen pyridine, benzoselenophene pyridine, and selenophene bipyridine; groups containing 2 to 10 ring structures, which may be cyclic aromatic or heteroaromatic groups of the same or different type and which are straight relative to one anotherLinked together or through at least one group selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an alicyclic group. Wherein Ar is₁～Ar₉May be further substituted, and the substituents may be selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl, and heteroaryl.

In one aspect, Ar₁～Ar₉May be independently selected from the group comprising the following structural units:

Y₀at each occurrence, is independently selected from C (R)²Or NR or O or S, X₀At each occurrence, independently selected from CR or N, and at each occurrence, independently selected from the group consisting of: hydrogen, deuterium, halogen atoms (F, Cl, Br, I), cyano, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, heteroalkyl, aryl and heteroaryl groups, n being selected from an integer from 1 to 20.

Further examples of cyclic aromatic amine derivative compounds can be found in US3567450, US4720432, US5061569, US3615404, and US 5061569.

Examples of metal complexes that may be used as HTMs or HIMs include, but are not limited to, the following general structures:

m is a metal having an atomic weight greater than 40;

(Y¹-Y²) Is a bidentate ligand, Y¹And Y²Independently selected from C, N, O, P and S; l is an ancillary ligand;

m is an integer having a value from 1 up to the maximum coordination number of the metal.

In one embodiment, (Y)¹-Y²) Is a 2-phenylpyridine derivative.

In another embodiment, (Y)¹-Y²) Is a carbene ligand.

In another embodiment, M is selected from Ir, Pt, Os, and Zn.

In another embodiment, the HOMO of the metal complex is greater than-5.5 eV (relative to vacuum level).

Examples of suitable HIM/HTM/EBM compounds are listed in the following table:

2. triplet Host material (Triplet Host):

examples of the triplet host material are not particularly limited, and any metal complex or organic compound may be used as the host as long as the triplet energy level thereof is higher than that of a light emitter, particularly a triplet light emitter or a phosphorescent light emitter.

Examples of metal complexes that can be used as triplet hosts (Host) include, but are not limited to, the following general structures:

m is a metal; (Y)³-Y⁴) Is a bidentate ligand, Y³And Y⁴Independently selected from C, N, O, P, and S; l is an ancillary ligand; m is an integer having a value from 1 to the maximum coordination number of the metal; in a preferred embodiment, the metal complexes useful as triplet hosts are of the form:

(O-N) is a bidentate ligand wherein the metal coordinates to both O and N atoms.m is an integer having a value from 1 up to the maximum coordination number for the metal;

in one embodiment, M may be selected from Ir and Pt.

Examples of the organic compound which can be a triplet host are selected from compounds containing a cyclic aromatic hydrocarbon group such as benzene, biphenyl, triphenylbenzene, benzofluorene; compounds containing aromatic heterocyclic groups, such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, dibenzocarbazole, indolocarbazole, pyridine indole, pyrrole bipyridine, pyrazole, imidazole, triazoles, oxazole, thiazole, oxadiazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, oxazole, dibenzooxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, phthalazine, quinazoline, quinoxaline, naphthalene, phthalein, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuran pyridine, furopyridine, benzothiophene pyridine, thiophene pyridine, benzoselenophene pyridine, and selenophene benzodipyridine; groups having 2 to 10 ring structures, which may be the same or different types of cyclic aromatic hydrocarbon groups or aromatic heterocyclic groups, are bonded to each other directly or through at least one group selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom, a boron atom, a chain structural unit and an alicyclic group. Wherein each Ar may be further substituted, and the substituents may be selected from the group consisting of hydrogen, deuterium, cyano, halogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl.

In a preferred embodiment, the triplet host material may be selected from compounds comprising at least one of the following groups:

wherein: x₀,Y₀Has the same meaning as above, Ar¹⁰～Ar³⁰Selected from aryl or heteroaryl, R may be selected from the following groups: hydrogen, deuterium, halogen atoms (F, Cl, Br, I), cyano, alkyl, alkoxy, amino, alkenyl, alkynyl, aralkyl, heteroalkyl, aryl and heteroaryl groups, n being selected from an integer from 1 to 20.

Examples of suitable triplet host materials are listed in the following table but are not limited to:

it is an object of the present invention to provide a material solution for evaporation type OLEDs.

In certain embodiments, the metal complexes according to the invention have a molecular weight of 1200g/mol or less, preferably 1100g/mol or less, very preferably 1000g/mol or less, more preferably 950g/mol or less, and most preferably 900g/mol or less.

It is another object of the present invention to provide a material solution for printing OLEDs.

In certain embodiments, the metal complexes according to the invention have a molecular weight of 800g/mol or more, preferably 900g/mol or more, very preferably 1000g/mol or more, more preferably 1100g/mol or more, most preferably 1200g/mol or more.

In further embodiments, the metal complexes according to the invention have a solubility in toluene of 2mg/ml or more, preferably 3mg/ml or more, more preferably 4mg/ml or more, most preferably 5mg/ml or more at 25 ℃.

The invention also relates to a composition comprising at least one pyrene quinone organic compound or high polymer or mixture as described above, and at least one organic solvent; the at least one organic solvent is selected from aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound, or boric acid ester or phosphoric acid ester compound, or a mixture of two or more solvents.

In a preferred embodiment, according to a composition of the invention, said at least one organic solvent is chosen from aromatic or heteroaromatic-based solvents.

Examples of aromatic or heteroaromatic-based solvents suitable for the present invention include, but are not limited to, p-diisopropylbenzene, pentylbenzene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1, 4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentylbenzene, tripentylbenzene, pentyltoluene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3, 4-tetramethylbenzene, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, butylbenzene, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2, 4-trichlorobenzene, 4-difluorodiphenylmethane, 1, 2-dimethoxy-4- (1-propenyl) benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α -dichlorodiphenylmethane, 4- (3-phenylpropyl) pyridine, 1, 2-dimethylquinoline, 2-benzoic acid, 2-isopropylquinoline, 2-benzoic acid, 2-ethyl benzoate, and the like.

Examples of aromatic ketone-based solvents suitable for the present invention are, but not limited to: 1-tetralone, 2- (phenylepoxy) tetralone, 6- (methoxy) tetralone, acetophenone, propiophenone, benzophenone, and derivatives thereof, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylpropiophenone, 3-methylpropiophenone, 2-methylpropiophenone, and the like.

Examples of aromatic ether-based solvents suitable for the present invention are, but not limited to: 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethylacetal, tetrahydro-2-phenoxy-2H-pyran, 1, 2-dimethoxy-4- (1-propenyl) benzene, 1, 4-benzodioxan, 1, 3-dipropylbenzene, 2, 5-dimethoxytoluene, 4-ethylphenetole, 1, 3-dipropoxybenzene, 1,2, 4-trimethoxybenzene, 4- (1-propenyl) -1, 2-dimethoxybenzene, 1, 3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-t-butylanisole, trans-p-propenylanisole, 1, 2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, methyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether;

in some preferred embodiments, the at least one organic solvent may be selected from: aliphatic ketones such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2, 5-hexanedione, 2,6, 8-trimethyl-4-nonanone, fenchylone, phorone, isophorone, di-n-amyl ketone, etc.; or aliphatic ethers such as amyl ether, hexyl ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, and the like.

In other preferred embodiments, the at least one organic solvent may be selected from ester-based solvents: alkyl octanoates, alkyl sebacates, alkyl stearates, alkyl benzoates, alkyl phenylacetates, alkyl cinnamates, alkyl oxalates, alkyl maleates, alkyl lactones, alkyl oleates, and the like. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate are particularly preferred.

The solvents mentioned may be used alone or as a mixture of two or more organic solvents.

In certain preferred embodiments, a composition according to the present invention comprises at least one organometallic complex or polymer or mixture as described above and at least one organic solvent, and may further comprise another organic solvent. Examples of another organic solvent include (but are not limited to): methanol, ethanol, 2-methoxyethanol, methylene chloride, chloroform, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1, 4-dioxane, acetone, methyl ethyl ketone, 1, 2-dichloroethane, 3-phenoxytoluene, 1,1, 1-trichloroethane, 1,1,2, 2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, decalin, indene, and/or mixtures thereof.

In some preferred embodiments, particularly suitable solvents for the present invention are those having Hansen (Hansen) solubility parameters within the following ranges:

δ_d(dispersion force) of 17.0 to 23.2MPa^1/2In particular in the range of 18.5 to 21.0MPa^1/2A range of (d);

δ_p(polar force) is 0.2 to 12.5MPa^1/2In particular in the range of 2.0 to 6.0MPa^1/2A range of (d);

δ_h(hydrogen bonding force) of 0.9 to 14.2MPa^1/2In particular in the range of 2.0 to 6.0MPa^1/2The range of (1).

The compositions according to the invention, in which the organic solvent is selected taking into account its boiling point parameter. In the invention, the boiling point of the organic solvent is more than or equal to 150 ℃; preferably equal to or more than 180 ℃; more preferably more than or equal to 200 ℃; more preferably more than or equal to 250 ℃; most preferably more than or equal to 275 ℃ or more than or equal to 300 ℃. Boiling points in these ranges are beneficial for preventing nozzle clogging in inkjet print heads. The organic solvent may be evaporated from the solvent system to form a thin film comprising the functional material.

In a preferred embodiment, the composition according to the invention is a solution.

In another preferred embodiment, the composition according to the invention is a suspension.

The composition of the embodiment of the present invention may contain the pyrene quinone organic compound or the high polymer or the mixture according to the present invention in an amount of 0.01 to 10 wt%, preferably 0.1 to 15 wt%, more preferably 0.2 to 5 wt%, most preferably 0.25 to 3 wt%.

The invention also relates to the use of said composition as a coating or printing ink for the production of organic electronic devices, particularly preferably by a printing or coating production process.

Suitable printing or coating techniques include, but are not limited to, ink jet printing, spray printing (Nozleprinting), letterpress printing, screen printing, dip coating, spin coating, doctor blade coating, roll printing, twist roll printing, lithographic printing, flexographic printing, rotary printing, spray coating, brush or pad printing, slot die coating, and the like. Gravure printing, jet printing and ink jet printing are preferred. The solution or suspension may additionally include one or more components such as surface active compounds, lubricants, wetting agents, dispersants, hydrophobing agents, binders, and the like, for adjusting viscosity, film forming properties, enhancing adhesion, and the like. For details on the printing technology and its requirements concerning the solutions, such as solvent and concentration, viscosity, etc., reference is made to the Handbook of Print Media, technology and production Methods, published by Helmut Kipphan, ISBN 3-540-67326-1.

The present invention also provides a use of the pyrene quinone Organic compound, the mixture or the composition as described above in an Organic electronic device, which may be selected from, but not limited to, an Organic Light Emitting Diode (OLED), an Organic photovoltaic cell (OPV), an Organic light emitting cell (OLEEC), an Organic Field Effect Transistor (OFET), an Organic light emitting field effect transistor (fet), an Organic laser, an Organic spintronic device, an Organic sensor, an Organic Plasmon emitting diode (Organic Plasmon emitting diode), and the like, and particularly preferably an OLED. In the embodiment of the present invention, the organic compound is preferably used for a hole injection or transport layer of an OLED device.

The invention further relates to an organic electronic device comprising at least one pyrene quinone organic compound, or mixture, as described above. Generally, such organic electronic devices comprise at least a cathode, an anode and a functional layer located between the cathode and the anode, wherein the functional layer comprises at least one organic compound as described above. The Organic electronic device can be selected from, but not limited to, Organic Light Emitting Diodes (OLEDs), Organic photovoltaic cells (OPVs), Organic light Emitting cells (OLEECs), Organic Field Effect Transistors (OFETs), Organic light Emitting field effect transistors (fets), Organic lasers, Organic spintronic devices, Organic sensors, Organic Plasmon Emitting diodes (Organic Plasmon Emitting diodes), and the like, and particularly preferred are Organic electroluminescent devices such as OLEDs, OLEECs, Organic light Emitting field effect transistors.

In certain particularly preferred embodiments, the electroluminescent device comprises a hole injection or transport layer comprising an organic compound or mixture as described above.

In the above-mentioned light emitting device, especially an OLED, it comprises a substrate, an anode, at least one light emitting layer, and a cathode.

The substrate may be opaque or transparent. A transparent substrate may be used to fabricate a transparent light emitting device. See, for example, Bulovic et al Nature 1996,380, p29, and Gu et al, appl.Phys.Lett.1996,68, p 2606. The substrate may be rigid or flexible. The substrate may be plastic, metal, semiconductor wafer or glass. Preferably, the substrate has a smooth surface. A substrate free of surface defects is a particularly desirable choice. In a preferred embodiment, the substrate is flexible, and may be selected from polymeric films or plastics having a glass transition temperature Tg of 150 deg.C or greater, preferably greater than 200 deg.C, more preferably greater than 250 deg.C, and most preferably greater than 300 deg.C. Examples of suitable flexible substrates are poly (ethylene terephthalate) (PET) and polyethylene glycol (2, 6-naphthalene) (PEN).

The anode may comprise a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into a Hole Injection Layer (HIL) or a Hole Transport Layer (HTL) or an emission layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the emitter in the light emitting layer or the p-type semiconductor material acting as a HIL or HTL or Electron Blocking Layer (EBL) is less than 0.5eV, preferably less than 0.3eV, most preferably less than 0.2 eV. Examples of anode materials include, but are not limited to: al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other suitable anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like. In certain embodiments, the anode is pattern structured. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

The cathode may comprise a conductive metal or metal oxide. The cathode can easily inject electrons into the EIL or ETL or directly into the light emitting layer. In one embodiment, the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the emitter in the light-emitting layer or of the n-type semiconductor material as Electron Injection Layer (EIL) or Electron Transport Layer (ETL) or Hole Blocking Layer (HBL) is less than 0.5eV, preferably less than 0.3eV, most preferably less than 0.2 eV. In principle, all materials which can be used as cathodes in OLEDs are possible as cathode materials for the device according to the invention. Examples of cathode materials include, but are not limited to: al, Au, Ag. Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF₂Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The cathode material may be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.

The OLED may also comprise further functional layers, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), a Hole Blocking Layer (HBL). Suitable materials for use in these functional layers are described in detail above and in WO2010135519a1, US20090134784a1 and WO2011110277a1, the entire contents of these 3 patent documents being hereby incorporated by reference.

Further, the Organic electronic device is an Organic Light Emitting Diode (OLED), an Organic photovoltaic cell (OPV), an Organic light Emitting cell (OLEEC), an Organic Field Effect Transistor (OFET), an Organic light Emitting field effect transistor (effet), an Organic laser, an Organic spintronic device, an Organic sensor, and an Organic Plasmon Emitting Diode (Organic plasma Emitting Diode).

In one embodiment, the present invention is an organic magnet comprising the above pyrenequinone based organic compound or its radical anion salt or dianion salt.

In one embodiment, the present invention is an organic semiconductor comprising the above pyrenequinone based organic compound or its radical anion salt or dianion salt.

Some more detailed descriptions (but not limited thereto) will be given below of the case where the pyrene quinone-based organic compound of the present invention is used in a layer of a hole transporting band region (hole injecting layer or hole transporting layer).

Next, the organic electronic device of the present invention will be explained.

The pyrene quinone-based organic compound of the present invention has one or more organic thin film layers including a light emitting layer between an anode and a cathode. At least one layer forming the organic thin film layer contains the pyrene quinone-based organic compound of the present invention.

As shown in fig. 1, in the organic electronic device, an anode (102), a Hole Injection Layer (HIL) (103), a Hole Transport Layer (HTL) (104), a light emitting layer (105), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL) or an Electron Transport Layer (ETL) (106), and a cathode (107) are stacked on a substrate (101) at a time, and in the device, an organic thin film layer has a stacked structure of the Hole Injection Layer (HIL) (103), the Hole Transport Layer (HTL) (104), the light emitting layer (105), the Electron Blocking Layer (EBL), the Electron Injection Layer (EIL), or the Electron Transport Layer (ETL) (106), and at least one of the layers forming the organic thin film layer contains the pyrene quinone-based organic compound of the present invention, whereby a driving voltage of the organic electronic device can be reduced and a long life can be achieved.

The content of the material is preferably 1 to 100 mol% with respect to the layer forming the organic thin film layer containing the pyrene quinone-based organic compound of the present invention.

In the organic electronic device of the present invention, a layer of a region (hole transport band region) between the anode (102) and the light-emitting layer (105), specifically, a Hole Injection Layer (HIL) (103) or a Hole Transport Layer (HTL) (104), is preferably the pyrene quinone type organic compound of the present invention. In addition, as in this embodiment, in an element having both a hole injection layer (103) and a hole transport layer (104), the hole transport layer (104) preferably contains the above-mentioned material.

When the pyrene quinone-based organic compound of the present invention is used for a layer of a hole transporting region, a hole injecting layer or a hole transporting layer may be formed solely from the compound of the present invention, or may be used in combination with other materials.

The light-emitting device according to the present invention emits light at a wavelength of 300 to 1200nm, preferably 350 to 1000nm, and more preferably 400 to 900 nm.

The invention also relates to the use of the electroluminescent device according to the invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.

The present invention will be described in connection with preferred embodiments, but the present invention is not limited to the following embodiments, and it should be understood that the appended claims outline the scope of the present invention and those skilled in the art, guided by the inventive concept, will appreciate that certain changes may be made to the embodiments of the invention, which are intended to be covered by the spirit and scope of the appended claims.