WO2020119503A1 - Organic electroluminescent device comprising light extraction layer, heteroatom polyaromatic ring compound, and composition - Google Patents

Abstract

The present invention relates to an organic electroluminescent device, comprising two electrodes, one or more organic functional layers provided between the two electrodes, and a light extraction layer provided on the side of an electrode surface away from the organic functional layer. A heteroatom polyaromatic ring compound used as a material of the light extraction layer possesses a suitable energy level, has a high extinction coefficient in the ultraviolet region, and has a high refractive index in the visible region, so that said compound can be used as the material of the light extraction layer in the device. The heteroatom polyaromatic ring compound of the present invention can reduce the damage of external high energy light to the internal material of the organic electroluminescent display device, improve light extraction, and improve the light emission efficiency of the device.

Description

Organic electroluminescent device including light extraction layer, heteroatom polyaromatic ring compound and composition Technical field

The invention relates to the technical field of organic electroluminescence, in particular to a class of organic electroluminescent devices having organic compounds with a relatively high refractive index as a light extraction layer material, and also relates to a heteroatom polyaromatic ring compound and its application in organic electroluminescence Applications in the field of luminescence.

Background technique

Organic electroluminescent display devices are a type of self-luminous display device, which generate excitons through the transfer and recombination of carriers between various functional layers, and rely on high quantum efficiency organic compounds or metal complexes to emit light. It has the characteristics of self-illumination, high brightness, high efficiency, high contrast and high responsiveness.

In recent years, the luminous efficiency of organic electroluminescent diodes (OLED) has been greatly improved, but its internal quantum efficiency has approached the theoretical limit. Therefore, improving light extraction efficiency has become an effective means to further improve device stability and current efficiency (such as the accumulation of metal complexes in the emitting layer, matching of refractive indexes between functional layers, etc.). In 2001, Hung et al. covered the surface of the metal cathode with a layer of organic and inorganic compounds of about 50 nm. By controlling the thickness and refractive index, the performance of the device was improved. In 2003, Riel et al. attempted to vapor-deposit the inorganic compound ZnSe with a high refractive index (n=2.6) on the cathode, using the difference in refractive index between the functional layers to improve the light extraction efficiency, but it was limited by the evaporation of inorganic materials Due to high temperature and slow evaporation rate, these compounds have not been used more in organic electroluminescent devices.

Therefore, a new class of materials that improve the light extraction efficiency of organic electroluminescent devices needs to be further developed.

Summary of the invention

In view of the above-mentioned shortcomings of the prior art, a main object of the present invention is to provide an organic electroluminescent device having an organic compound with a higher refractive index as a light extraction layer to improve the light extraction efficiency of the device.

Such compounds need to meet the following conditions: in the ultraviolet band (<400nm), the extinction coefficient is high to avoid the harmful effects of harmful light on the device materials; in the visible range (>430nm), the extinction coefficient is close to 0, which has a higher visible light Transmittance reduces the impact on the light output efficiency of the device; it has a higher refractive index and a smaller difference in the visible light range, has the characteristics of improving light output and optimizing the device structure, etc.; it has a higher glass transition temperature and improves the thermal stability of the compound.

The technical solution of the present invention is as follows:

The invention relates to an organic electroluminescent device comprising two electrodes, one or more organic functional layers arranged between the two electrodes, and an organic functional layer arranged on the surface of an electrode and away from the organic functional layer A light extraction layer on one side, the material of the light extraction layer contains a compound represented by the general formula (1):

among them:

Each time X ₁ , X ₂ and X ₃ appear, they are independently selected from NR ₁ , O, S and Se;

Each time Q ₁ , Q ₂ and Q ₃ appear, they are independently selected from N and CR _{2 respectively} ;

Ar ₁ , Ar ₂ and Ar _{3 are} each independently selected from hydrogen, cyano, substituted or unsubstituted aromatic or heteroaromatic groups with 5 to 60 ring atoms, substituted or unsubstituted Non-aromatic ring systems with 3 to 25 ring atoms, or substituted or unsubstituted arylamine groups;

Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from: single bond, alkenyl, alkynyl, acyl, amide, carbonyl, sulfone, substituted or unsubstituted carbon atoms of 1 to 60 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aromatic groups or heteroaromatic groups having 5 to 60 ring atoms;

Each occurrence of R ₁ and R ₂ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 C-atom straight-chain thioalkoxy group, branched or cyclic alkyl group having 3 to 20 C atoms, branched or cyclic alkoxy group having 3 to 20 C atoms, having 3 to 20 20 C atom branched or cyclic thioalkoxy group, silyl group, keto group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano (-CN), carbamoyl (-C(=O)NH2), haloformyl, formyl (-C(=O)-H), isocyano, isocyanate , Thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups or heterocycles with 5 to 60 ring atoms An aromatic group, an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

The present invention further relates to a heteroatom polyaromatic ring compound selected from the structures described in general formula (3):

among them:

Each time X ₁ , X ₂ and X ₃ appear, they are independently selected from NR ₁ , O, S and Se;

Ar ₂ and Ar _{3 are} each independently selected from the group consisting of hydrogen, cyano, substituted or unsubstituted aromatic or heteroaromatic groups with 5 to 60 ring atoms, and substituted or unsubstituted ring atoms A non-aromatic ring system of 3 to 25, or a substituted or unsubstituted arylamine group;

Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from: single bond, alkenyl, alkynyl, acyl, amide, carbonyl, sulfone, substituted or unsubstituted carbon atoms of 1 to 60 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted ring atoms having 5 to 60 ring atoms Heteroaromatic groups;

Ar _{1 is} selected from one or a combination of the following groups:

among them:

Each time X ₄ appears, it is independently selected from NR ₅ , CR ₅ R ₆ , O, S, Se;

Each time Y ₁ ～Y ₁₃ appears, it is independently selected from N or CR ₇ , at least one of Y ₉ ～Y ₁₃ is N;

Each time Z ₁ appears, it is independently selected from NR ₈ , O, and S;

Each occurrence of R ₁ to R ₈ and R ₁₃ to R ₁₅ is independently selected from the group consisting of hydrogen, D, a linear alkyl group having 1 to 20 C atoms, and a linear alkoxy group having 1 to 20 C atoms Group, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms Oxygen groups, branched or cyclic thioalkoxy groups having 3 to 20 C atoms, silyl groups, keto groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms , Aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, An aryloxy group having 5 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

The invention also relates to a composition comprising at least one heteroatom polyaromatic compound as described above and at least one organic solvent.

The present invention also relates to a light extraction layer material, characterized in that it contains a heteroatom polyaromatic compound as described above.

Beneficial effect:

The heteroatom polyaromatic ring compound according to the present invention has a higher glass transition temperature and a higher thermal stability of the compound as a material for the light extraction layer of the organic electroluminescent device. The heteroatom polyaromatic compound of the present invention has a high extinction coefficient in the ultraviolet band, a small extinction coefficient in the visible light range, and a high refractive index. When used as a light extraction layer of an electronic device, the heteroatom polyaromatic compound of the present invention can avoid the harmful effects of harmful light on the internal materials of the device and improve the efficiency of visible light extraction.

BRIEF DESCRIPTION

Figure 1 is a schematic diagram of an embodiment of a device. 1 is a structural view of a light emitting device according to an embodiment of the present invention, in the figure 1 is a substrate, 2 is an anode, 3a is a hole injection layer (HIL), 3b is a hole transport layer (HTL), 3c is a light emitting layer , 3d is the electron transport layer (ETL), 3e is the electron injection layer (EIL), 4 is the cathode, and 5 is the light extraction layer;

2 is the ultraviolet-visible absorption spectrum of Synthesis Example C7 in a dichloromethane solution;

FIG. 3 is the ultraviolet-visible absorption spectrum of Synthesis Example C8 in a methylene chloride solution.

detailed description

The present invention provides an organic electroluminescence device containing a heteroatom polyaromatic ring compound as a material for a light extraction layer. The invention also relates to a heteroatom polyaromatic ring compound. To make the objectives, technical solutions, and effects of the present invention clearer and more specific, the present invention will be described in further detail below. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not intended to limit the present invention.

In the present invention, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.

In the present invention, the "number of ring atoms" means that the structural compound obtained by atom bonding to form a ring (for example, a monocyclic compound, a fused ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) constitutes the ring itself. The number of atoms in the atom. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the benzene ring has 6 ring atoms, the naphthalene ring has 10 ring atoms, and the thienyl ring has 5 ring atoms.

In the present invention, "adjacent groups" means that these groups are bonded to the same carbon atom or to adjacent carbon atoms. These definitions apply correspondingly to "adjacent substituents".

Aromatic group refers to a hydrocarbon group containing at least one aromatic ring. Heteroaromatic group refers to an aromatic hydrocarbon group containing at least one heteroatom. Further, the hetero atom is selected from Si, N, P, O, S, and/or Ge, and further, selected from Si, N, P, O, and/or S. A fused ring aromatic group means that the ring of the aromatic group may have two or more rings, in which two carbon atoms are shared by two adjacent rings, that is, a fused ring. A fused heterocyclic aromatic group refers to a fused ring aromatic hydrocarbon group containing at least one heteroatom. For the purposes of the present invention, aromatic groups or heteroaromatic groups include not only aromatic ring systems but also non-aromatic ring systems. Therefore, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, etc. are for the purposes of the present invention , Also considered to be aromatic groups or heterocyclic aromatic groups. For the purposes of the present invention, a fused ring aromatic or fused heterocyclic aromatic ring system includes not only a system of aromatic groups or heteroaromatic groups, but also, where multiple aromatic groups or heterocyclic aromatic groups can also be short Non-aromatic unit discontinuities (<10% of non-H atoms, further less than 5% of non-H atoms, such as C, N or O atoms). Therefore, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diarylether, etc., are also considered to be fused ring aromatic ring systems for the purposes of the present invention.

In the present invention, the "light extraction layer" refers to a layer located on the surface of the electrode of the organic electroluminescence device opposite to the surface facing the organic functional layer.

The invention provides an organic electroluminescent device, which comprises: two electrodes, one or more organic functional layers disposed between the two electrodes, and light disposed on the surface of an electrode and away from the organic functional layer An extraction layer, the material of the light extraction layer contains a compound represented by the general formula (1):

Wherein: X ₁ , X ₂ , and X ₃ are independently selected from NR ₁ , O, S, and Se each time they appear; further, each time X ₁ , X ₂ , and X ₃ are independently selected from O, S; In one embodiment, X ₁ , X ₂ , and X _{3 are} selected from the same group. Further, X ₁ , X ₂ , and X _{3 are} both selected from O or S.

Each time Q ₁ , Q ₂ , and Q ₃ appear, they are independently selected from N and CR ₂ ; further, each time Q ₁ , Q ₂ , and Q ₃ appear, they independently select CR ₂ ;

Ar ₁ , Ar ₂ and Ar _{3 are} each independently selected from hydrogen, cyano, substituted or unsubstituted aromatic or heteroaromatic groups with 5 to 60 ring atoms, substituted or unsubstituted Non-aromatic ring systems with 3 to 25 ring atoms, or substituted or unsubstituted arylamine groups;

Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from: single bond, alkenyl, alkynyl, acyl, amide, carbonyl, sulfone, substituted or unsubstituted carbon atoms of 1 to 60 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, or substituted or unsubstituted ring atoms having 5 to 60 ring atoms Of heteroaromatic groups;

Each occurrence of R ₁ and R ₂ is independently selected from the group consisting of hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, and having 1 to 20 C-chain straight-chain thioalkoxy groups, branched or cyclic alkyl groups with 3 to 20 C atoms, alkoxy groups with 3 to 20 C atoms or sulfur with 3 to 20 C atoms Substituted alkoxy, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano (- CN), carbamoyl (-C(=O)NH2), haloformyl, formyl (-C(=O)-H), isocyano, isocyanate, thiocyanate, isothiocyanate, Hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted with 5 to 60 ring atoms Heteroaromatic groups, aryloxy groups having 5 to 60 ring atoms, heteroaryloxy groups having 5 to 60 ring atoms, or a combination of these groups.

An organic electroluminescent device refers to a device that emits light when a certain voltage is applied, and generally includes two electrodes and a light emitting layer, and some organic electroluminescent devices further include a light extraction layer. The organic electroluminescent device of the present invention may be selected from organic light emitting diodes (OLED), organic light emitting cells (OLEEC), organic field effect tubes (OFET), and organic light emitting field effect tubes.

In one embodiment, the organic electroluminescent device of the present invention is an organic light emitting diode (OLED), including an anode, a cathode, a light emitting layer, and a light extraction layer. In one embodiment, the organic electroluminescent device of the present invention, wherein the light extraction layer is located on the surface of the cathode.

In one embodiment, according to the organic electroluminescent device of the present invention, Ar ₁ in the general formula (1) may be selected from one or a combination of the following groups:

Among them: each time X ₄ appears, it is independently selected from NR ₅ , CR ₅ R ₆ , O, S, Se; each time Y ₁ ～Y ₁₃ appears, it is independently selected from N or CR ₇ , Y ₉ ～Y _At least one of ₁₃ is N; each time Z ₁ appears, it is independently selected from NR ₈ , O, and S;

Each occurrence of R ₃ to R ₈ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 C-atom straight-chain thioalkoxy group, branched or cyclic alkyl group having 3 to 20 C atoms, branched or cyclic alkoxy group having 3 to 20 C atoms, having 3 to 20 Branched or cyclic thioalkoxy group of 20 C atoms, silyl group, ketone group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, having 5 to 60 rings An aryloxy group of atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

In one embodiment, Ar ₁ in the general formula (1) may be selected from one or a combination of the following groups:

In one embodiment, at least one of Y ₁ to Y _{5 is} selected from N; preferably, Y _{5 is} selected from N; in one embodiment, at least two of Y ₁ to Y ₅ are selected from N; preferably, Y ₁ and Y _{5 is} selected from N; in one embodiment, at least three of Y ₁ to Y ₅ are selected from N; preferably, Y ₁ , Y ₄ and Y _{5 are} selected from N.

In one embodiment, Y ₉ ~ Y ₁₃ is at least two N; In one embodiment, Y ₉ ~ Y ₁₃ are N.

Further, Ar ₁ in the general formula (1) may be selected from one of the following groups or a combination thereof:

Wherein: n1 represents an integer of 0 to 5; an integer of 0 to 4, n2 represents; N3 represents an integer of 0 to 2; N4 represents an integer of 0 to 3; N5 represents an integer of 0 to 6; R ₃ ~ R ₅ and R ₇ , R ₈ has the same meaning as above.

In one embodiment, according to the organic electroluminescent device of the present invention, Ar ₂ and Ar ₃ may be selected from one or a combination of the following groups:

Where: X is CR ₉ or N; W is selected from CR ₉ R ₁₀ , NR ₉ , C (=O), O, S, Se;

Each occurrence of R ₉ to R ₁₀ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 C-atom straight-chain thioalkoxy group, branched or cyclic alkyl group having 3 to 20 C atoms, branched or cyclic alkoxy group having 3 to 20 C atoms, having 3 to 20 Branched or cyclic thioalkoxy group of 20 C atoms, silyl group, ketone group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, having 5 to 60 rings An aryloxy group of atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

Ar ₄ and Ar _{5 are} selected from: substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, heteroaromatic groups, or substituted or A non-aromatic ring system with 3 to 25 unsubstituted ring atoms.

In an embodiment, Ar ₂ and Ar ₃ may be selected from one or a combination of the following groups:

In one embodiment, Ar ₂ and Ar ₃ are selected from one or a combination of the following groups:

Further, Ar ₂ and Ar ₃ may be selected from one or a combination of the following groups:

Among them: the H atom on the ring may be further substituted.

In certain preferred embodiments, Ar ₂ and Ar _{3 are} selected from the same structure; in certain preferred embodiments, Ar ₂ and Ar _{1 are} selected from the same structure; in certain more preferred embodiments, Ar ₂ and Ar _{3 are} selected from the same structure as Ar ₁ . Preferably, Ar ₂ , Ar ₃ and Ar _{1 are} simultaneously selected from the following groups:

In one embodiment, according to the organic electroluminescent device of the present invention, L ₁ , L ₂ , and L _{3 are} selected from single bonds or one or a combination of the following groups:

Wherein, X and W have the meanings described above.

Further, L ₁ , L ₂ and L _{3 are} selected from single bonds or substituted or

In one embodiment, the material of the light extraction layer is selected from any compound of the general formula (2-1) to (2-15):

Among them, the meanings of L ₁ to L ₃ , X ₁ to X ₃ , R ₂ , Y ₁ to Y ₁₃ , Z ₁ , X ₄ , X, W, Ar ₄ to Ar _{5 are} as described above.

Specifically, according to the organic electroluminescent device of the present invention, the material of the light extraction layer is selected from the following structures but not limited to:

Among them: H in the above structure may be further substituted arbitrarily.

According to the organic electroluminescent device of the present invention, the material of the light extraction layer needs a higher glass transition temperature to improve the thermal stability of the material of the light extraction layer. In some embodiments, the glass transition temperature T _g ≥100°C, in one embodiment, T _g ≥120°C, in yet another embodiment, T _g ≥140°C, in yet another embodiment, T _g ≥160°C, in another embodiment, _Tg ≥180°C.

In some embodiments, according to the organic electroluminescent device of the present invention, the material of the light extraction layer has a refractive index greater than 1.7 at a wavelength of 630 nm; further, the material of the light extraction layer has a refractive index greater than 1.78 at a wavelength of 630 nm; Furthermore, the material of the light extraction layer has a refractive index greater than 1.83 at a wavelength of 630 nm.

In other embodiments, according to the organic electroluminescent device of the present invention, the material singlet energy (S1) of the light extraction layer is greater than or equal to 2.7 eV; further, the material singlet energy (S1) of the light extraction layer Greater than or equal to 2.8 eV; further, the material singlet energy (S1) of the light extraction layer is greater than or equal to 2.85 eV.

In other embodiments, according to the organic electroluminescent device of the present invention, the material singlet energy (S1) of the light extraction layer is less than or equal to 3.1 eV; further, the material singlet energy (S1) of the light extraction layer Less than or equal to 3.0eV.

According to the organic electroluminescent device of the present invention, the material of the light extraction layer needs a smaller extinction coefficient, and the extinction coefficient at a wavelength of 430 nm is less than 0.1; further, the extinction coefficient at a wavelength of 430 nm is less than 0.003; more Further, the extinction coefficient at a wavelength of 430 nm is less than 0.001. It has a higher transmittance for visible light and reduces the impact on the light output efficiency of the device.

In some embodiments, according to the organic electroluminescent device of the present invention, the light extraction layer has a larger extinction coefficient in the wavelength range of ≤400 nm; further, the extinction coefficient ≥0.3 at the wavelength of 350 nm; further Ground, the extinction coefficient at a wavelength of 350 nm is ≥0.5; still further, the extinction coefficient at a wavelength of 350 nm is ≥0.7, and in particular, the extinction coefficient at a wavelength of 350 nm is ≥1.0.

In some embodiments, the organic electroluminescent device according to the present invention is an organic light emitting diode, in which the light extraction layer is located on the surface of the cathode.

In one embodiment, the organic electroluminescent device according to the present invention includes one or more organic functional layers selected from the group consisting of an electron injection layer, an electron transport layer, and a hole injection layer. One or more layers of a hole transport layer and a light-emitting layer, at least one of which includes a light-emitting layer.

In some embodiments, the organic electroluminescent device according to the present invention, wherein the light-emitting material in the light-emitting layer is selected from a singlet emitter, a triplet emitter, or a TADF material.

In certain embodiments, the organic electroluminescent device according to the present invention, wherein the organic functional layer is selected from a hole transport layer, a light emitting layer, and an electron transport layer.

The singlet emitter, triplet emitter and TADF materials are described in more detail below (but not limited to this).

1. Singlet luminous body

Singlet luminophores often have longer conjugated π electron systems. So far, there have been many examples, such as styrene amine and its derivatives disclosed in WO2001021729A1, indenofluorene and its derivatives disclosed in WO2008/006449 and triarylamine derivatives of pyrene disclosed in US7233019.

In one embodiment, the singlet luminophore can be selected from monostyrene amine, distyrene amine, tristyrene amine, quaternary styrene amine, styrene phosphine, styrene ether and aromatic amine.

Monostyrene amine refers to a compound that contains an unsubstituted or substituted styryl group and at least one amine, especially aromatic amines. Binary styrylamine refers to a compound that contains two unsubstituted or substituted styryl groups and at least one amine, especially aromatic amines. Ternary styrene amine refers to a compound that contains three unsubstituted or substituted styryl groups and at least one amine, especially aromatic amines. Quaternary styrene amine refers to a compound that contains four unsubstituted or substituted styryl groups and at least one amine, especially aromatic amines. In one embodiment, styrene is stilbene, which may be further substituted. The corresponding definitions of phosphines and ethers are similar to amines. Arylamine or aromatic amine refers to a compound that contains three unsubstituted or substituted aromatic ring or heterocyclic ring systems directly linked to nitrogen. At least one of these aromatic or heterocyclic ring systems is a condensed ring system, especially at least 14 aromatic ring atoms. Examples include aromatic anthracene amine, aromatic anthracene diamine, aromatic pyrene amine, aromatic pyrene diamine, aromatic ketamine and aromatic chloramine. Aromatic anthracene refers to a compound in which a binary arylamine group is directly attached to anthracene, especially at the 9 position. An aromatic anthracene diamine refers to a compound in which two binary aryl amine groups are directly linked to anthracene, especially at the 9,10 position. The definitions of aromatic pyrene amine, aromatic pyrene diamine, aromatic pyridylamine and aromatic pyrendylamine are similar, in particular, in which the binary arylamine group is linked to the 1 or 1, 6 position of pyrene.

Examples of singlet emitters based on vinylamine and aromatic amines can be found in the following patent documents: WO2006/000388, and US2008/0113101A1 The entire contents of the patent documents listed above are hereby incorporated by reference .

Examples of singlet luminophores based on stilbene and its derivatives are US5121029.

Further singlet emitters can be selected from indenofluorene-amine and indenofluorene-diamine, as disclosed in WO2006/122630, benzoindenofluorene-amine and benzoindenofluorene-diamine, such as As disclosed in WO2008/006449, dibenzoindenofluorene-amine and dibenzoindenofluorene-diamine are disclosed in WO2007/140847.

Further singlet emitters can be selected from fluorene-based fused ring systems, as disclosed in US2015333277A1, US2016204355A1.

Further singlet emitters can be selected from pyrene derivatives, such as the structure disclosed in US2013175509A1; pyrene triarylamine derivatives, such as pyrene triarylamine derivatives containing dibenzofuran units disclosed in CN102232068B; others The triarylamine derivative of pyrene with a specific structure is disclosed as CN105085334A. Other materials that can be used as singlet emitters are polycyclic aromatic hydrocarbon compounds, especially derivatives of the following compounds: anthracene such as 9,10-bis(2-naphthoanthracene), naphthalene, tetrabenzene, xanthene, phenanthrene , Pyrene (such as 2,5,8,11-tetra-t-butylperylene), indenopyrene, phenylene such as (4,4'-bis(9-ethyl-3-carbazolyl vinyl)-1 ,1'-biphenyl), diindenopyrene, decacycloene, hexabenzobenzene, fluorene, spirobifluorene, arylpyrene, arylene vinyl, cyclopentadiene such as tetraphenylcyclopentadiene, Rubrene, coumarin, rhodamine, quinacridone, pyran such as 4(dicyanomethylene)-6-(4-p-dimethylaminostyryl-2-methyl)-4H -Pyran (DCM), thiopyran, bis(azinyl)imine boron compound, bis(azinyl)methylene compound, carbostyryl compound, oxazinone, benzoxazole, benzothiazole, benzo Imidazole and pyrrolopyrrole dione. Some singlet emitter materials can be found in the following patent documents: US 20070252517 A1, US 2007/0252517 A1. The entire contents of the patent documents listed above are hereby incorporated by reference.

The following table lists some examples of suitable singlet emitters:

2. Triplet luminophore

Triplet emitters are also called phosphorescent emitters. In one embodiment, the triplet luminophore is a metal complex with the general formula M(L)n, where M is a metal atom, and L can be the same or different each time it appears, and is an organic ligand, which Bonded or coordinated to the metal atom M through one or more positions, n is an integer between 1 and 6. Further, the triplet luminophore contains a chelating ligand, that is, a ligand, which is coordinated to the metal through at least two binding points, and it is further considered that the triplet luminophore contains two or three identical or different doublets Tooth or multidentate ligands. Chelating ligands help to improve the stability of metal complexes. In one embodiment, the metal complex that can be used as a triplet emitter has the following form:

The metal atom M is selected from: a transition metal element, a lanthanide element, or an actinide element. Further, the metal atom M is selected from Ir, Pt, Pd, Au, Rh, Ru, Os, Re, Cu, Ag, Ni, Co, W or Eu. Furthermore, the metal atom M is selected from Ir, Au, Pt, W or Os.

Ar ⁴ and Ar ⁵ may be the same or different each time they appear. It is a cyclic group. Ar ₁ contains at least one donor atom, that is, an atom with a lone pair of electrons, such as nitrogen. Through the donor atom, the cyclic group The group is coordinately connected to the metal; where Ar ₂ contains at least one carbon atom, the cyclic group is connected to the metal through the carbon atom; Ar ₁ and Ar ₂ are linked together by a covalent bond, which can each carry one or more substitutions Groups, they can also be linked together by substitution groups; L'can be the same or different each time it appears, it is a bidentate chelating auxiliary ligand, especially a monoanionic bidentate chelating ligand; q1 It can be 0, 1, 2 or 3, further, q1 is 2 or 3; q2 can be 0, 1, 2 or 3, further, q2 is 1 or 0. Examples of organic ligands may be selected from phenylpyridine derivatives or 7,8-benzoquinoline derivatives. All these organic ligands may be substituted, for example by alkyl chains or fluorine or silicon. In one embodiment, the auxiliary ligand may be selected from acetone acetate or picric acid.

Some examples of triplet emitter materials and their applications can be found in the following patent documents and documents: WO2005033244, WO2005019373, US20050258742, WO2014007565, Baldoal. Nature (2000), 750. The entire contents of the patent documents and documents listed above are hereby incorporated by reference. Some examples of suitable triplet emitters are listed in the table below:

3. Thermally activated delayed fluorescent luminescent material (TADF)

Traditional organic fluorescent materials can only use 25% singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). Although the phosphorescent material enhances the intersystem crossing due to the strong spin-orbit coupling at the center of the heavy atom, the singlet excitons and triplet excitons formed by electrical excitation can be effectively used to emit light, so that the internal quantum efficiency of the device reaches 100%. However, the phosphorescent materials are expensive, the material stability is poor, and the device efficiency roll-off is severe, which limits its application in OLEDs. Thermally activated delayed fluorescent luminescent materials are the third generation of organic luminescent materials developed after organic fluorescent materials and organic phosphorescent materials. Such materials generally have a small singlet-triplet energy level difference (ΔE _st ), and triplet excitons can be converted into singlet excitons to emit light by crossing between anti-systems. This can make full use of the singlet excitons and triplet excitons formed under electrical excitation. The quantum efficiency within the device can reach 100%. At the same time, the material structure is controllable, the properties are stable, the price is cheap and no precious metals are needed, and the application prospect in the field of OLED is broad.

The TADF material needs to have a small singlet-triplet energy level difference, further ΔEst<0.3eV, further ΔEst<0.2eV, and further ΔEst<0.1eV. In one embodiment, the TADF material has a relatively small ΔEst. In another embodiment, TADF has a better fluorescence quantum efficiency. Some TADF luminescent materials can be found in the following patent documents: CN103483332(A), TW201309696(A), US20120217869(A1), WO2013133359(A1), Adachi, et.al.Adv.Mater., 21, 2009, 4802, Adachi, et.al.Appl.Phys.Lett., 98, 2011, 083302, Adachi, et.al.Appl.Phys.Lett., 101, 2012, 093306, hereby list the patents or article files listed above The entire contents are incorporated into this article for reference.

Some examples of suitable TADF luminescent materials are listed in the table below:

The organic electroluminescent device according to the present invention may be selected from, but not limited to: organic light emitting diode (OLED), organic light emitting battery, organic light emitting field effect tube, organic laser, etc., especially OLED.

The cathode, anode and light extraction layer of the device structure of the organic electroluminescent device will be described below, but not limited to this.

The anode may contain a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into the hole injection layer (HIL) or the hole transport layer (HTL) or the light emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the HOMO energy level or valence band energy level of the luminous body in the light emitting layer or the p-type semiconductor material as HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, further, the absolute value is less than 0.3 eV, and further, the absolute value is 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 easily selected and used by those of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, etc. In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare organic electroluminescent devices according to the present invention.

The cathode may contain a conductive metal or metal oxide. The cathode can easily inject electrons into EIL or ETL or directly into the light emitting layer. In one embodiment, the work function of the cathode and the LUMO level or conductivity of the n-type semiconductor material in the light-emitting body in the light-emitting layer or as an electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) The absolute value of the difference in band levels is less than 0.5 eV. Further, the absolute value is less than 0.3 eV, and further, the absolute value is less than 0.2 eV. In principle, all materials that can be used as cathodes for OLEDs are possible as cathode materials for the devices of the invention. Examples of cathode materials include, but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF ₂ /Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, etc.

The light extraction layer needs to have a suitable energy level structure, and has strong absorption in the region with a wavelength of less than 400nm, and visible light with a wavelength of more than 400nm absorbs weakly or close to zero, so as to avoid damage to the internal material of the device by high-energy light in the subsequent process. At the same time, the light extraction layer has a high refractive index, which can beneficially derive the emission of visible light and improve the luminous efficiency of the organic electronic light-emitting device. When the reflectivity of the interface between the light extraction layer and the adjacent electrode is large, the influence of light interference is large. Therefore, the refractive index of the material constituting the light extraction layer is greater than that of the adjacent electrode, and the refractive index is at 630 nm It may be 1.50 or more, and furthermore, the refractive index is 1.70 or more at 630 nm, and furthermore, the refractive index is 1.80 or more at 630 nm.

In some embodiments, according to the organic electroluminescent device of the present invention, the thickness of the organic compound of the light extraction layer is generally 10 nm to 200 nm; further, the thickness of the organic compound of the light extraction layer is 20 nm to 150 nm; The compound thickness is 30 nm to 100 nm; in particular, the light extraction layer organic compound thickness is 40 nm to 90 nm.

The present invention also relates to the application of the electroluminescent device according to the present invention in various electronic equipment, including, but not limited to, display equipment, lighting equipment, light sources, sensors, and the like.

The present invention further relates to a heteroatom polyaromatic ring compound having the structural formula represented by the general formula (3):

among them:

Each time X ₁ , X ₂ and X ₃ appear, they are independently selected from NR ₁ , O, S and Se;

Ar ₂ and Ar _{3 are} each independently selected from the group consisting of hydrogen, cyano, substituted or unsubstituted aromatic or heteroaromatic groups with 5 to 60 ring atoms, and substituted or unsubstituted ring atoms A non-aromatic ring system of 3 to 25, or a substituted or unsubstituted arylamine group;

Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from: single bond, alkenyl, alkynyl, acyl, amide, carbonyl, sulfone, substituted or unsubstituted carbon atoms of 1 to 60 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted ring atoms having 5 to 60 ring atoms Heteroaromatic groups;

Ar _{1 is} selected from one or a combination of the following groups:

among them:

Each time Y ₁ ～Y ₅ appears, it is independently selected from N or CR ₇ ;

Each time Z ₁ appears, it is independently selected from NR ₈ , O, and S;

Each occurrence of R ₁ , R ₇ to R ₈ , R ₃ to R ₄ , and R ₁₃ to R ₁₅ is independently selected from the group consisting of: hydrogen, D, linear alkyl having 1 to 20 C atoms, and having 1 to Linear alkoxy with 20 C atoms, linear thioalkoxy with 1 to 20 C atoms, branched or cyclic alkyl with 3 to 20 C atoms, with 3 to 20 C Atom branched or cyclic alkoxy group, branched or cyclic thioalkoxy group having 3 to 20 C atoms, silyl group, keto group having 1 to 20 C atoms, having 2 to Alkoxycarbonyl group of 20 C atoms, aryloxycarbonyl group having 7 to 20 C atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate, thiocyanate, isothio Cyanate, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, substituted or unsubstituted aromatic group with 5 to 60 ring atoms, substitution with 5 to 60 ring atoms Or an unsubstituted heteroaromatic group, an aryloxy group having 5 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

Further, Ar ₂ and Ar ₃ may be selected from one or a combination of the following groups:

among them:

X is CR ₉ or N; W is selected from CR ₉ R ₁₀ , NR ₉ , C (=O), O, S, Se;

Each occurrence of R ₉ to R ₁₀ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 C-atom straight-chain thioalkoxy group, branched or cyclic alkyl group having 3 to 20 C atoms, branched or cyclic alkoxy group having 3 to 20 C atoms, having 3 to 20 Branched or cyclic thioalkoxy group of 20 C atoms, silyl group, ketone group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, having 5 to 60 rings An aryloxy group of atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

Ar ₄ and Ar _{5 are} selected from: substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, heteroaromatic groups, or substituted or A non-aromatic ring system with 3 to 25 unsubstituted ring atoms.

In an embodiment, Ar ₂ and Ar ₃ may be selected from one or a combination of the following groups:

In one embodiment, Ar ₂ and Ar ₃ are selected from one or a combination of the following groups:

In certain preferred embodiments, Ar ₂ and Ar _{3 are} selected from the same structure;

In certain preferred embodiments, Ar ₂ and Ar ₃ may be selected from the following structures;

In certain preferred embodiments, Ar ₂ and Ar ₃ is selected from at least one structure; preferably, Ar ₂ and Ar ₃ are selected from the following structures;

In certain more preferred embodiments, Ar ₂ and Ar _{3 are} selected from the same structure as Ar ₁ . Preferably, Ar ₂ , Ar ₃ and Ar _{1 are} simultaneously selected from the following groups:

Further, the structure described in the general formula (3) may be any compound selected from the general formulas (4-1) to (4-9):

Furthermore, the structure described in the general formula (3) can be selected from any compound of the general formulas (5-1) to (5-9):

Wherein: X ₁ to X ₃ , L ₁ to L ₃ , R ₁₃ to R ₁₅ , and Ar ₄ to Ar ₅ have the same meanings as above; R ₇ and R ₉ have the same meanings; n1 is selected from integers of 0 to 4; n2 is selected from An integer from 0 to 3; n3 is selected from an integer from 0 to 5.

In an embodiment, n1, n2, and n3 are all selected from 0.

In one embodiment, each occurrence of X ₁ , X ₂ , and X ₃ is independently selected from O and S; in one embodiment, X ₁ , X ₂ , and X _{3 are} selected from the same group, further , X ₁ , X ₂ and X _{3 are} both selected from O or S.

In one embodiment, according to the compound of the present invention, L ₁ to L ₃ are all selected from single bonds or phenyl groups.

Specifically, the compound according to the present invention is selected from any one of the structural formulas (G-41)-(G-120) described above, but is not limited thereto.

The heteroatom polyaromatic compound according to the present invention can be applied not only to the light extraction layer of organic electroluminescent devices, but also to other organic functional layers, such as: electron injection layer, electron transport layer, hole injection layer, Hole transport layer and light emitting layer.

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

In some embodiments, the molecular weight of the heteroatom polyaromatic ring compound of the present invention is ≤1200 g/mol, further, the molecular weight of the heteroatom polyaromatic ring compound of the present invention is ≤1100 g/mol, and further, the heteroatom of the present invention The molecular weight of the atomic polyaromatic ring compound ≤ 1000 g/mol, and furthermore, the molecular weight of the heteroatom polyaromatic ring compound of the present invention ≤ 950 g/mol, in particular, the molecular weight of the heteroatom polyaromatic ring compound of the present invention ≤ 900 g/mol .

Another object of the invention is to provide a material solution for printed OLEDs.

In certain embodiments, the molecular weight of the heteroatom polyaromatic ring compound of the present invention is ≥800 g/mol. Further, the molecular weight of the heteroatom polyaromatic ring compound of the present invention is ≥900 g/mol. The molecular weight of the atomic polyaromatic ring compound is ≥1000g/mol, and furthermore, the molecular weight of the heteroatom polyaromatic ring compound of the present invention is ≥1100g/mol, in particular, the molecular weight of the heteroatom polyaromatic ring compound of the present invention is ≥1200g/mol .

In other embodiments, the heteroatom polyaromatic compound of the present invention has a solubility in toluene of ≥ 2 mg/ml at 25°C, further, a solubility in toluene of ≥ 3 mg/ml, and further, in toluene The solubility in ≥ 4mg/ml, in particular, the solubility in toluene ≥ 5mg/ml.

The invention also relates to a composition comprising at least one compound as described above and at least one organic solvent; said at least one organic solvent is selected from: aromatic, heteroaromatic, ester, aromatic ketone , Aromatic ethers, aliphatic ketones, aliphatic ethers, alicyclics, olefin compounds, borate esters, phosphate ester compounds, or a mixture of two or more solvents.

The invention further relates to an organic electronic device comprising at least one compound as described above. The organic electronic device according to the present invention may be selected from, but not limited to, organic light emitting diodes (OLED), organic photovoltaic cells, organic light emitting cells, organic field effect tubes, organic light emitting field effect tubes, organic lasers, organic spin electrons Devices, organic sensors and organic plasmon emitting diodes, especially OLED.

The present invention will be described below in conjunction with embodiments, but the present invention is not limited to the following embodiments. It should be understood that the appended claims summarize the scope of the present invention. Guided by the concept of the present invention, those skilled in the art should realize that certain changes to the embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

Specific examples

The present invention will be described below with specific examples, but the present invention is not limited to the following examples. It should be understood that the appended claims summarize the scope of the invention. Under the guidance of the inventive concept, those skilled in the art should realize that certain changes made to the embodiments of the present invention will be covered by the scope of the claims of the present invention.

The structure of the synthesis example is as follows:

Compound C-1 synthesis:

Weigh I-1 (2g, 4.64mmol), I-2 (4.8g, 15mmol), potassium carbonate (4.14g, 30mmol), tetrakis(triphenylphosphine) palladium (268mg, 0.23mmol) into 250mL double mouth In the flask, 150 mL of a mixed solvent of toluene and methanol was added, nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave 1.62 g of the target product with a yield of 45%.

Compound C-2 synthesis:

Weigh I-1 (1.26g, 2.92mmol), I-3 (3.84g, 12mmol), potassium carbonate (3.73g, 27mmol), tetrakis (triphenylphosphine) palladium (173mg, 0.15mmol) was added 100mL of bis In a neck flask, 60 mL of a mixed solvent of toluene and methanol was added. Nitrogen was purged and replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave the target product 1.4g, yield 62%.

Synthesis of compound C-3:

Weigh I-1 (1.27g, 2.94mmol), I-4 (3.85g, 12mmol), potassium carbonate (3.73g, 27mmol), tetrakis (triphenylphosphine) palladium (173mg, 0.15mmol) was added 100mL of bis In a neck flask, 60 mL of a mixed solvent of toluene and methanol was added, the nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, the organic solvent was distilled off under reduced pressure, and the silica gel sample column chromatography was used to obtain the target product 1.6g, yield 70%.

Synthesis of compound C-4:

Weigh I-5 (1.15g, 2.4mmol), I-2 (3.08g, 9.6mmol), potassium carbonate (3.04g, 22mmol), tetrakis (triphenylphosphine) palladium (138mg, 0.12mmol) was added to 250mL of In a double-necked flask, 150 mL of a mixed solvent of toluene and methanol was added, nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added and extracted with ethyl acetate. The organic phase was washed with brine and dried over sodium sulfate. The organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave 1.27 g of the target product with a yield of 64%.

Synthesis of compound C-5:

Weigh I-5 (1.43g, 2.97mmol), I-3 (3.84g, 12mmol), potassium carbonate (3.73g, 27mmol), tetrakis (triphenylphosphine) palladium (273mg, 0.15mmol) was added 100mL of bis In a neck flask, 60 mL of a mixed solvent of toluene and methanol was added, the nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave 1.1 g of the target product in 45% yield.

Synthesis of compound C-6:

Weigh out I-5 (2g, 4.2mmol), 9,9-dimethylfluorene-2-boronic acid (0.95g, 4.2mmol), potassium carbonate (2g, 15mmol), tetrakis(triphenylphosphine)palladium (145mg , 0.13 mmol) was added to a 250 mL double-necked flask, 100 mL of a mixed solvent of toluene and methanol was added, nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave the target product 1.46g, yield 64%.

Weigh I-6 (1.4g, 2.56mmol), I-7 (1.8g, 5.6mmol), potassium carbonate (1.8g, 13mmol), tetrakis (triphenylphosphine) palladium (92mg, 0.08mmol) was added to 250mL of In a double-necked flask, add 100 mL of a mixed solvent of toluene and methanol, replace with nitrogen three times, raise the temperature to 90°C, and stir overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave 1.43 g of the target product, with a yield of 72%.

Compound C-7 synthesis:

Weigh 1,3,5-trifluoro-2,4,6-triiodobenzene (3g, 3.92mmol), I-8 (2.72g, 12.5mmol), bis (triphenylphosphine) palladium chloride (0.21 g, 0.3 mmol), cuprous iodide (57 mg, 0.3 mmol) was added to a 250 mL double-necked flask, 80 mL of tetrahydrofuran and 20 mL of triethylamine were added, the nitrogen was replaced three times, the temperature was raised to 45°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, the organic phase was separated, extracted with ethyl acetate, the organic phases were combined, the organic solvent was distilled off under reduced pressure, and the silica gel sample column chromatography was used to obtain the target product 2g, yield 45%.

Weigh I-9 (2g, 2.55mmol), cesium hydroxide (3.75g, 25mmol), add a 100mL double-necked flask, add about 60mL of N,N-dimethylacetamide, replace nitrogen three times, and warm to reflux, Stir overnight. After the reaction liquid was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave the target product 1.2g, yield 60%.

Compound C-8 synthesis:

Weigh out I-5 (1.85g, 3.86mmol), 9,9-dimethylfluorene-2-boronic acid (3.69g, 15.5mmol), potassium carbonate (4.97g, 36mmol), tetrakis(triphenylphosphine)palladium (219 mg, 0.19 mmol) was added to a 100 mL double-necked flask, 60 mL of a mixed solvent of toluene and methanol was added, nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave the target product 1.3g, yield 41%.

Compound C-9 synthesis:

Weigh I-5 (2.03g, 4.24mmol), 9,9-dimethylfluorene-2-boronic acid (4.05g, 17mmol), potassium carbonate (4.97g, 36mmol), tetrakis(triphenylphosphine) palladium ( 243 mg, 0.21 mmol) was added to a 100 mL double-necked flask, 60 mL of a mixed solvent of toluene and methanol was added, nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, the organic solvent was distilled off under reduced pressure, and the silica gel sample column chromatography was used to obtain the target product 1.5g, yield 50%.

Weigh out I-10 (1.5g, 2.1mmol), diphenylamine (0.42g, 2.5mmol), tris(dibenzylideneacetone) dipalladium (55mg, 0.06mmol), sodium tert-butoxide (0.24g, 2.5mmol) ), add a 250mL double-necked flask, add 70mL of toluene, replace the nitrogen three times, increase the temperature to 100 ℃, and stir overnight. After the reaction solution was cooled to room temperature, water was added, the organic phase was separated, extracted with ethyl acetate, the organic phases were combined, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave 1.38 g of the target product with a yield of 82%.

Compound C-10 synthesis:

Weigh I-6 (2.03g, 5.43mmol), boric acid (5.02g, 16mmol), potassium carbonate (4.14g, 30mmol), tetrakis(triphenylphosphine) palladium (312mg, 0.27mmol) into a 100mL double-necked flask Then, 70 mL of a mixed solvent of toluene and methanol was added, nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave 1.8 g of the target product with a yield of 45%.

Weigh out I-11 (1.58g, 2.14mmol), diphenylamine (0.42g, 2.5mmol), tris(dibenzylideneacetone) dipalladium (55mg, 0.06mmol), sodium tert-butoxide (0.24g, 2.5mmol) ), add a 100mL double-necked flask, add 60mL of toluene, replace nitrogen three times, warm up to 100 °C, and stir overnight. After the reaction solution was cooled to room temperature, water was added, the organic phase was separated, extracted with ethyl acetate, the organic phases were combined, the organic solvent was distilled off under reduced pressure, and silica gel sample column chromatography was used to obtain the target product 1.2g, yield 68%.

Compound C-11 synthesis:

Weigh I-6 (2.03g, 5.78mmol), borate (5.46g, 17mmol), potassium carbonate (4.97g, 36mmol), tetrakis(triphenylphosphine) palladium (334mg, 0.29mmol) and add 100mL of bis In a neck flask, 60 mL of a mixed solvent of toluene and methanol was added, the nitrogen was replaced three times, the temperature was raised to 90°C, and the mixture was stirred overnight. After the reaction solution was cooled to room temperature, water was added, extracted with ethyl acetate, the organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave the target product 2.1g, yield 55%.

Weigh 1-12 (1.71g, 2.58mmol), borate (0.96g, 3mmol), potassium carbonate (1.24g, 9mmol), tetrakis(triphenylphosphine) palladium (150mg, 0.13mmol) and add 100mL of bis In a neck flask, add 40 mL of a mixed solvent of toluene and methanol, replace with nitrogen three times, raise the temperature to 90°C, and stir overnight. After the reaction solution was cooled to room temperature, water was added and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, and the organic solvent was distilled off under reduced pressure. The silica gel sample column chromatography gave 1.4 g of the target product with a yield of 70%.

Compound C-12 synthesis:

Place Intermediate I-11 (4g, 14.3mmol) in a reaction vessel filled with nitrogen, add ethanol and pyridine (50mmol), then add Intermediate 2 (1.5g, 50mmol), heat to reflux, after the reaction is complete, heat Filtration gave a yellow solid. The solid was washed with ethanol, dried under reduced pressure without further treatment, put into dry methylene chloride, added DDQ (11.35g, 50mmol), and stirred at room temperature, after the reaction was complete, the system was washed with water, the solvent was concentrated and used Dichloromethane recrystallized to obtain compound 4.24g, total yield 38%

Energy structure of organic compounds

The energy levels of organic materials can be obtained through quantum calculations, such as the use of TD-DFT (time-dependent density functional theory) through Gaussian09W (Gaussian Inc.). The specific simulation method can be found in WO2011141110. First use the semi-empirical method "Ground State/DFT/Default Spin/B3LYP/6-31G(d)" (Charge 0/Spin) Singlet to optimize the molecular geometry, then the energy structure of the organic molecule is determined by TD-DFT (time-dependent density) (Functional theory) method calculated "TD-SCF/DFT/Default Spin/B3PW91" and the base group "6-31G(d)" (Charge0/SpinSinglet).

The compound was deposited on single crystal silicon by vacuum evaporation to form a 50nm thin film. The single crystal silicon was placed on an ellipsometer (ES-01) sample stage at an incident angle of 70°. The test was atmospheric environment and the extinction coefficient of the compound ( k) and refractive index (n) test results are obtained by ellipsometer.

Among them, CBP is 4,4'-bis(9-carbazole) biphenyl

The results are shown in Table 1:

Table 1

Chemical compound	S1(eV)	Extinction Department @430nm	Refractive index@630nm
C-1	2.87	0.05	1.82
C-2	2.83	0.02	1.80
C-3	3.03	0.01	1.81
C-4	2.89	0.02	1.80
C-5	2.83	0.03	1.79
C-6	3.08	0.01	1.80
C-7	3.17	0	1.77
C-8	3.13	0	1.76
C-9	2.94	0.03	1.78
C-10	3.07	0.01	1.79
C-11	2.87	0.04	1.80
C-12	3.01	0	1.82
CBP	3.44	0	1.74

It can be seen from Table 1 that the above compounds C-1 to C-12 all have a large refractive index (greater than 1.7), and a higher refractive index can ensure a better light extraction effect; the singlet energy of the above compounds is higher , So that the absorption can be concentrated in the ultraviolet band; Figure 2 is the ultraviolet-visible absorption spectrum of compound C-7 in dichloromethane solution concentration of 10mg/L, and Figure 3 is the concentration of compound C-8 in dichloromethane solution 10mg/L It can be seen that the above compounds have higher absorption in the ultraviolet band and weak absorption in the visible band, which can resist the damage of external high-energy light to the inside of the device.

Preparation and characterization of OLED devices

The following describes the preparation process of the OLED device by using specific embodiments in detail. The structure of the OLED device is: ITO/Ag/ITO (anode)/HATCN/SFNFB/m-CP:Ir(p-ppy) ₃ /NaTzF ₂ /LiF/Mg:Ag/light extraction layer, the preparation steps are as follows:

The anode layer of ITO conductive glass was cleaned, followed by ultrasonic cleaning with deionized water, acetone, and isopropyl alcohol for 15 minutes, and then treated in a plasma cleaner for 5 minutes to improve the electrode work function. On the ITO anode layer, the hole injection layer material HATCN is evaporated by vacuum evaporation, the thickness is 5 nm, and the evaporation rate

On the hole injection layer, the hole transport material SNFFB was evaporated by vacuum evaporation with a thickness of 80 nm. A light-emitting layer is vapor-deposited on the hole transport layer, m-CP is used as a host material, Ir(p-ppy) _{3 is} used as a doping material, and the mass ratio of Ir(p-ppy) ₃ and m-CP is 1:9. The thickness is 30 nm. On the light-emitting layer, the electron transport material NaTzF _{2 was} evaporated by vacuum evaporation, with a thickness of 30 nm. On the electron transport layer, an electron injection layer LiF was vacuum-evaporated with a thickness of 1 nm, and this layer was the electron injection layer 7. Above the electron injection layer, a cathode Mg:Ag layer was vacuum-evaporated with a Mg:Ag doping ratio of 9:1 and a thickness of 15 nm. On the cathode layer, the light extraction layer compound C-1 was vapor-deposited by a vacuum vapor deposition method, and the thickness was 60 nm.

Organic electroluminescent device Example 2: The light extraction layer compound of the organic electroluminescent device becomes C-3.

Organic electroluminescent device Example 3: The light extraction layer compound of the organic electroluminescent device becomes C-6.

Organic electroluminescent device Example 4: The light extraction layer compound of the organic electroluminescent device becomes C-7.

Organic electroluminescent device Example 5: The light extraction layer compound of the organic electroluminescent device becomes C-9.

Organic electroluminescent device Example 6: The light extraction layer compound of the organic electroluminescent device becomes C-10.

Organic electroluminescent device Example 7: The light extraction layer compound of the organic electroluminescent device becomes C-12.

Organic electroluminescent device Comparative Example 1: The light extraction layer compound of the organic electroluminescent device becomes CBP.

The structures of compounds involved in organic electroluminescent devices are as follows:

Table 2

Numbering	Light extraction layer compound	Luminous efficiency (cd/A)
1	C-1	110
2	C-3	118
3	C-6	113
4	C-7	102
5	C-9	102
6	C-10	104
7	C-12	112
8	CBP	87

The luminous efficiency in Table 2 is the data obtained when the current density is 10 mA/cm ² . It can be seen from Table 2 that the compound of the present invention can effectively improve the luminous efficiency of an organic electroluminescent device as a light extraction layer compared to a comparative example.

The above-mentioned embodiments only express several embodiments of the present invention, and their descriptions are more specific and detailed, but they should not be construed as limiting the scope of the invention patent. It should be noted that, for a person of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can also be made, which all fall within the protection scope of the present invention. Therefore, the protection scope of the invention patent shall be subject to the appended claims.

Claims (19)

1. An organic electroluminescent device comprising two electrodes, one or more organic functional layers disposed between the two electrodes, and a light extraction layer disposed on the surface of an electrode and away from the organic functional layer, characterized by The reason is that the material of the light extraction layer contains the compound represented by the general formula (1):

   

   among them:

   Each time X ₁ , X ₂ and X ₃ appear, they are independently selected from NR ₁ , O, S and Se;

   Each time Q ₁ , Q ₂ and Q ₃ appear, they are independently selected from N and CR _{2 respectively} ;

   Ar ₁ , Ar ₂ and Ar _{3 are} each independently selected from hydrogen, cyano, substituted or unsubstituted aromatic or heteroaromatic groups with 5 to 60 ring atoms, substituted or unsubstituted Non-aromatic ring systems with 3 to 25 ring atoms, or substituted or unsubstituted arylamine groups;

   Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from: single bond, alkenyl, alkynyl, acyl, amide, carbonyl, sulfone, substituted or unsubstituted carbon atoms of 1 to 60 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted ring atoms having 5 to 60 ring atoms Heteroaromatic groups;

   Each occurrence of R ₁ and R ₂ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 C-atom straight-chain thioalkoxy group, branched or cyclic alkyl group having 3 to 20 C atoms, branched or cyclic alkoxy group having 3 to 20 C atoms, having 3 to 20 Branched or cyclic thioalkoxy group of 20 C atoms, silyl group, ketone group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, having 5 to 60 rings An aryloxy group of atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
2. The organic electroluminescent device according to claim 1, wherein Ar _{1 is} selected from one or a combination of the following groups:

   

   among them:

   Each time X ₄ appears, it is independently selected from NR ₅ , CR ₅ R ₆ , O, S, Se;

   Each time Y ₁ ～Y ₁₃ appears, it is independently selected from N or CR ₇ , at least one of Y ₉ ～Y ₁₃ is N;

   Each time Z ₁ appears, it is independently selected from NR ₈ , O, and S;

   Each occurrence of R ₃ to R ₈ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 Straight-chain thioalkoxy groups with 3 C atoms, branched or cyclic alkyl groups with 3 to 20 C atoms, branched or cyclic alkoxy groups with 3 to 20 C atoms, with 3 to 20 C atom branched or cyclic thioalkoxy, silyl, ketone group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, having 5 to 60 rings An aryloxy group of atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
3. The organic electroluminescent device according to claim 2, characterized in that Ar _{1 is} selected from one or a combination of the following groups:

   
4. The organic electroluminescent device according to claim 2, characterized in that Ar _{1 is} selected from one or a combination of the following groups:

   

   Among them: n1 represents an integer of 0-5; n2 represents an integer of 0-4; n3 represents an integer of 0-2; n4 represents an integer of 0-3; n5 represents an integer of 0-6.
5. The organic electroluminescent device according to any one of claims 1 to 4, characterized in that Ar ₂ and Ar _{3 can be} selected from one or a combination of the following groups:

   

   among them:

   X is CR ₉ or N;

   W is selected from CR ₉ R ₁₀ , NR ₉ , C (=O), O, S, Se;

   Each occurrence of R ₉ to R ₁₀ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 C-atom straight-chain thioalkoxy group, branched or cyclic alkyl group having 3 to 20 C atoms, branched or cyclic alkoxy group having 3 to 20 C atoms, having 3 to 20 Branched or cyclic thioalkoxy group of 20 C atoms, silyl group, ketone group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, having 5 to 60 rings An aryloxy group of atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

   Ar ₄ and Ar _{5 are} selected from: substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, heteroaromatic groups, or substituted or A non-aromatic ring system with 3 to 25 unsubstituted ring atoms.
6. The organic electroluminescent device according to claim 5, wherein: Ar ₂ and Ar _{3 can be} selected from one or a combination of the following groups:

   
7. The organic electroluminescent device according to any one of claims 1 to 6, characterized in that: L ₁ , L ₂ and L _{3 are} independently selected from single bonds or one or a combination of the following groups:

   

   among them:

   X is CR ₉ or N;

   W is selected from CR ₉ R ₁₀ , NR ₉ , C (=O), O, S, Se;

   Each occurrence of R ₉ to R ₁₀ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 C-atom straight-chain thioalkoxy group, branched or cyclic alkyl group having 3 to 20 C atoms, branched or cyclic alkoxy group having 3 to 20 C atoms, having 3 to 20 Branched or cyclic thioalkoxy group of 20 C atoms, silyl group, ketone group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, having 5 to 60 rings An aryloxy group of atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
8. The organic electroluminescent device according to claim 7, wherein L ₁ , L ₂ and L _{3 are} independently selected from single bonds or

   
9. The organic electroluminescent device according to any one of claims 1-8, wherein the material of the light extraction layer is selected from any compound of the general formula (2-1) to (2-15):

   

   
10. The organic electroluminescent device according to any one of claims 1-9, wherein the material of the light extraction layer has a refractive index greater than 1.7 at a wavelength of 630 nm.
11. The organic electroluminescent device according to any one of claims 1-10, wherein the material singlet energy (S1) of the light extraction layer is greater than 2.7 eV.
12. The organic electroluminescent device according to any one of claims 1 to 11, wherein the material of the light extraction layer has an extinction coefficient of less than 0.1 at a wavelength of 430 nm.
13. The organic electroluminescent device according to any one of claims 1-12, wherein the organic electroluminescent device is an organic light emitting diode, wherein the light extraction layer is located on a cathode surface of the organic light emitting diode on.
14. A heteroatom polyaromatic ring compound selected from the structure described in the general formula (3):

    

    among them:

    Each time X ₁ , X ₂ and X ₃ appear, they are independently selected from NR ₁ , O, S and Se;

    Ar ₂ and Ar _{3 are} each independently selected from the group consisting of hydrogen, cyano, substituted or unsubstituted aromatic or heteroaromatic groups with 5 to 60 ring atoms, and substituted or unsubstituted ring atoms A non-aromatic ring system of 3 to 25, or a substituted or unsubstituted arylamine group;

    Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from: single bond, alkenyl, alkynyl, acyl, amide, carbonyl, sulfone, substituted or unsubstituted carbon atoms of 1 to 60 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 60 carbon atoms, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted ring atoms having 5 to 60 ring atoms Heteroaromatic groups;

    Ar _{1 is} selected from one or a combination of the following groups:

    

    among them:

    Each time Y ₁ ～Y ₅ appears, it is independently selected from N or CR ₇ ;

    Each time Z ₁ appears, it is independently selected from NR ₈ , O, and S;

    Each occurrence of R ₁ , R ₇ to R ₈ , R ₃ to R ₄ , and R ₁₃ to R ₁₅ is independently selected from the group consisting of: hydrogen, D, linear alkyl having 1 to 20 C atoms, and having 1 to Linear alkoxy with 20 C atoms, linear thioalkoxy with 1 to 20 C atoms, branched or cyclic alkyl with 3 to 20 C atoms, with 3 to 20 C Atom branched or cyclic alkoxy group, branched or cyclic thioalkoxy group having 3 to 20 C atoms, silyl group, keto group having 1 to 20 C atoms, having 2 to Alkoxycarbonyl group of 20 C atoms, aryloxycarbonyl group having 7 to 20 C atoms, cyano group, carbamoyl group, haloformyl group, formyl group, isocyano group, isocyanate, thiocyanate, isothio Cyanate, hydroxyl, nitro, CF3, Cl, Br, F, crosslinkable group, substituted or unsubstituted aromatic group with 5 to 60 ring atoms, substitution with 5 to 60 ring atoms Or an unsubstituted heteroaromatic group, an aryloxy group having 5 to 60 ring atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
15. The heteroatom polyaromatic ring compound according to claim 14, wherein Ar ₂ and Ar _{3 are} selected from one or a combination of the following groups:

    

    among them:

    X is CR ₉ or N;

    W is selected from CR ₉ R ₁₀ , NR ₉ , C (=O), O, S, Se;

    Each occurrence of R ₉ to R ₁₀ is independently selected from: hydrogen, D, a linear alkyl group having 1 to 20 C atoms, a linear alkoxy group having 1 to 20 C atoms, and having 1 to 20 C-atom straight-chain thioalkoxy group, branched or cyclic alkyl group having 3 to 20 C atoms, branched or cyclic alkoxy group having 3 to 20 C atoms, having 3 to 20 Branched or cyclic thioalkoxy group of 20 C atoms, silyl group, ketone group having 1 to 20 C atoms, alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atom aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF3, Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atoms, having 5 to 60 rings An aryloxy group of atoms, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

    Ar ₄ and Ar _{5 are} selected from: substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, heteroaromatic groups, or substituted or A non-aromatic ring system with 3 to 25 unsubstituted ring atoms.
16. The heteroatom polyaromatic ring compound according to claim 15, wherein the structure of the general formula (3) can be selected from any compound of the general formula (4-1) to (4-9):

    
17. The heteroatom polyaromatic ring compound according to any one of claims 14 to 16, wherein L ₁ to L ₃ are all selected from a single bond or a phenyl group.
18. A composition characterized by comprising at least one heteroatom polyaromatic compound as claimed in any one of claims 14-17, and at least one organic solvent.
19. A light extraction layer material characterized by comprising the heteroatom polyaromatic ring compound according to any one of claims 14-17.

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