CN112864334B - Organic electroluminescent device containing light extraction layer material - Google Patents

Abstract

In order to improve device performance, particularly light extraction efficiency, of an organic electroluminescent device, the present invention provides an organic electroluminescent device comprising a light extraction layer, wherein the light extraction layer material is selected from triarylamine compounds containing triphenylene and an electron-withdrawing group. The light extraction material provided by the invention has a higher extinction coefficient in an ultraviolet region and a higher refractive index in a visible light region, can reduce the damage of external high-energy light to the internal material of the organic electroluminescent display device, and improves the light extraction rate and the luminous efficiency of the device.

Description

Organic electroluminescent device containing light extraction layer material

This application claims the priority of a Chinese patent application filed with the China Patent Office on November 12, 2019, with application number 201911098682.3 and invention name “An organic electroluminescent device containing light extraction layer material”, the entire contents of which are incorporated by reference in this application.

Technical Field

The present invention relates to the technical field of organic electroluminescence, and in particular to an organic electroluminescent device containing a light extraction layer material. The present invention further relates to an organic compound and its application in an organic electroluminescent device.

Background Art

Organic electroluminescent display devices are a type of self-luminous display device that generates excitons through the transfer and recombination of carriers between various functional layers, and emits light through organic compounds or metal complexes with high quantum efficiency. It has the characteristics of self-luminescence, high brightness, high efficiency, high contrast, and high responsiveness.

In recent years, the luminous efficiency of organic light-emitting diodes (OLEDs) has been greatly improved, but its internal quantum efficiency has approached the theoretical limit. Therefore, improving the light extraction efficiency has become an effective means to further improve the stability and current efficiency of the device (such as the accumulation of metal complexes in the emission layer, matching the refractive index between functional layers, etc.).

OLED generally adopts a top emission structure that emits light from the top. In such a light-emitting device, when the light emitted from the light-emitting layer is incident on other functional layers, if it is incident at an angle above a certain angle, total reflection occurs between the light-emitting layer and the other functional layers. Therefore, only a part of the emitted light can be used. In recent years, in order to improve the efficiency of light extraction, it has been proposed to set a light extraction layer on the outside of a semi-transparent electrode with a low refractive index. For example, in 2001, Hung et al. covered the surface of a metal cathode with a layer of organic or inorganic compounds of about 50nm, and improved the performance of the device by controlling the thickness and refractive index. In 2003, Riel et al. tried to evaporate ZnSe, an inorganic compound with a high refractive index (n=2.6), on the cathode, and used the difference in refractive index between the functional layers to improve the light extraction efficiency. However, due to the high evaporation temperature and slow evaporation rate of inorganic materials, this type of compound has not been widely used 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 deficiencies of the prior art, a main object of the present invention is to provide an organic electroluminescent device containing a light extraction layer to improve the light extraction efficiency of the device. The present invention further provides a new organic compound and its application in an organic electroluminescent device.

In view of the above reasons, it is possible to try to use organic compounds with a higher refractive index in electroluminescent devices to improve light extraction efficiency. Such compounds must meet the following conditions: high extinction coefficient in the ultraviolet band (<400nm) to avoid the adverse effects of harmful light on device materials; extinction coefficient close to 0 in the visible light range (>430nm), high transmittance to visible light, and reduced impact on the light extraction efficiency of the device; high refractive index in the visible light range with small difference, with the characteristics of improving light extraction and optimizing device structure; high glass transition temperature to improve the thermal stability of the compound.

The technical solution of the present invention is as follows:

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

in:

L ₁ , L ₂ and L ₃ are independently selected from a single bond, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring system having 3 to 30 ring atoms;

Ar ₁ is selected from an electron withdrawing group; Ar ₂ is selected from a substituted or unsubstituted condensed ring aromatic group or condensed ring heteroaromatic group having 10 to 30 ring atoms;

Each occurrence of V is independently selected from CR ₁ or N;

_R1 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, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, _CF3 , Cl, Br, F, a cross-linkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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 present invention further relates to an organic compound selected from the structure shown in the general formula (4):

in:

_L1 and _L3 are independently selected from a single bond, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring system having 3 to 30 ring atoms;

_L2 is selected from a single bond or any one of the following groups:

W, _W1 each occur independently selected from _CR9 or N;

Y ₂ and Y ₃ are each independently selected from NR ₁₀ , CR ₁₀ R ₁₁ , O, S, SiR ₁₀ R ₁₁ , S═O, SO ₂ or PR ₁₀ ;

_R9 , _R10 and _R11 are each 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, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl 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, a cross-linkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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 present invention relates to a composition comprising at least one organic compound as mentioned above and at least one organic solvent.

The present invention relates to a light extraction layer material, comprising the above-mentioned organic compound.

Beneficial effects:

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

BRIEF DESCRIPTION OF THE DRAWINGS

Fig. 1 is a schematic diagram of a device embodiment. Fig. 1 is a structural diagram of a light-emitting device according to an embodiment of the present invention, in which 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 an electron transport layer (ETL), 3e is an electron injection layer (EIL), 4 is a cathode, and 5 is a light extraction layer;

FIG2 is a UV-visible absorption spectrum of compound C2 in dichloromethane;

FIG3 is a mass spectrum of compound C2.

DETAILED DESCRIPTION

The present invention provides an organic electroluminescent device comprising a triphenylene triarylamine compound as a material for a light extraction layer. The present invention also relates to an organic compound containing triphenylene. In order to make the purpose, technical solution and effect of the present invention clearer and more specific, the present invention is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

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

In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined groups are substituted, it is understood that they are optionally substituted by groups acceptable in the art, including but not limited to: C _1-30 alkyl, cycloalkyl containing 3-20 ring atoms, heterocyclyl containing 3-20 ring atoms, aryl containing 5-20 ring atoms, heteroaryl containing 5-20 ring atoms, silanyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, -NRR', cyano, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, nitro or halogen, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R and R' in -NRR' are each independently substituted by groups acceptable in the art, including but not limited to _{H, C 1-6 alkyl} , cycloalkyl containing 3-8 ring atoms, heterocyclyl containing 3-8 ring atoms, aryl containing 5-20 ring atoms or heteroaryl containing 5-10 ring atoms; the C The _{C 1-6} alkyl, cycloalkyl containing 3-8 ring atoms, heterocyclyl containing 3-8 ring atoms, aryl containing 5-20 ring atoms or heteroaryl containing 5-10 ring atoms are optionally further substituted by one or more of the following groups: C _1-6 alkyl, cycloalkyl containing 3-8 ring atoms, heterocyclyl containing 3-8 ring atoms, halogen, hydroxyl, nitro or amino.

In the present invention, the "number of ring atoms" refers to the number of atoms in the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring atoms. The same is true for the "number of ring atoms" described below unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5.

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 to "adjacent substituents" accordingly.

Aromatic groups refer to hydrocarbon groups containing at least one aromatic ring. Heteroaromatic groups refer to aromatic hydrocarbon groups containing at least one heteroatom. Further, the heteroatom is selected from Si, N, P, O, S and/or Ge, and further, is selected from Si, N, P, O and/or S. Condensed ring aromatic groups refer to aromatic groups whose rings may have two or more rings, in which two carbon atoms are shared by two adjacent rings, i.e., condensed rings. Condensed heterocyclic aromatic groups refer to condensed ring aromatic hydrocarbon groups containing at least one heteroatom. For the purposes of the present invention, aromatic groups or heteroaromatic groups include not only systems of aromatic rings, 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 also considered to be aromatic groups or heterocyclic aromatic groups for the purposes of the present invention. For the purposes of the present invention, fused aromatic or fused heteroaromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also systems in which multiple aromatic or heteroaromatic groups may be interrupted by short non-aromatic units (<10% non-H atoms, further less than 5% non-H atoms, such as C, N or O atoms). Thus, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamines, diaryl ethers, etc., are also considered fused aromatic ring systems for the purposes of the present invention.

In a preferred embodiment, the condensed ring aromatic group is selected from: naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, dinaphthylene, tetracene, pyrene, benzopyrene, acenaphthene, fluorene, and derivatives thereof; the condensed ring heteroaromatic group is selected from: benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furanopyrrole, furanofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, o-naphthylidene, quinoxaline, phenanthridine, primary idine, quinazoline, quinazolinone, and derivatives thereof.

In the present invention, the “light extraction layer” refers to a layer located on the electrode surface of the organic electroluminescent device and away from the organic functional layer.

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

in:

L ₁ , L ₂ and L ₃ are independently selected from a single bond, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring system having 3 to 30 ring atoms;

Ar ₁ is selected from an electron-withdrawing group; Ar ₂ is selected from a substituted or unsubstituted condensed ring aromatic group or condensed ring heteroaromatic group having 10-30 ring atoms; the molar refractive index of the condensed ring is relatively high, which can effectively increase the refractive index of the molecule;

Each occurrence of V is independently selected from CR ₁ or N; preferably, each occurrence of V is independently selected from CR ₁ ;

_R1 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, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, _CF3 , Cl, Br, F, a cross-linkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

In one embodiment, Ar ₂ is selected from a substituted or unsubstituted condensed aromatic group or condensed heteroaromatic group having 14-30 ring atoms; In one embodiment, Ar ₂ is selected from a substituted or unsubstituted condensed aromatic group having 14-30 ring atoms;

In one embodiment, Ar ₂ is selected from any group of (A-1)-(A-5):

in:

Each occurrence of X is independently selected from CR ₂ or N; when X is linked to L ₂ , X is selected from C; preferably, each occurrence of X is selected from CR ₂ ;

_R2 is independently selected at each occurrence from the group consisting of hydrogen, D, linear alkyl having 1 to 20 C atoms, linear alkoxy having 1 to 20 C atoms, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, _CF3 , Cl, Br, F, a cross-linkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

Further, Ar ₂ is selected from (A-1), (A-2) or (A-4); further, Ar ₂ is selected from (A-1).

In one embodiment, Ar ₂ is selected from any one of the following groups, wherein the H atoms on the ring may be further substituted:

Further, Ar ₂ is selected from

更进一步，Ar₂选自

Further, Ar ₂ is selected from

Furthermore, Ar ₂ is selected from

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

Wherein: X, V, L ₁ , L ₂ , L ₃ and Ar ₁ have the same meanings as above.

In one embodiment, in the general formulae (2-1) to (2-4), V is selected from CR ₁ ; further, R ₁ is selected from H; in one embodiment, in the general formulae (2-1) to (2-4), X is selected from CR ₂ ; further, R ₂ is selected from H; in one embodiment, in the general formulae (2-1) to (2-4), V is selected from CR ₁ , and X is selected from CR ₂ .

In one embodiment, the general formula (2-1)-(2-4) is selected from the following general formula:

In one embodiment, _Ar1 is selected from an electron-withdrawing group; the reason is that it can improve the electron push-pull of the entire molecule, regulate the energy level and dipole moment of the molecule, and improve the ultraviolet absorption of the molecule at a wavelength below 400 nm and the refractive index of the molecule.

Further, Ar ₁ is selected from any one of the following groups:

in:

Each occurrence of X ₁ is independently selected from CR ₃ or N, and at least one X ₁ is selected from N; in one embodiment, at least 2 X ₁ are selected from N;

Y is independently selected at each occurrence from NR ₄ , CR ₄ R ₅ , O, S, SiR ₄ R ₅ , S═O, SO ₂ or PR ₄ ;

R ₃ , R ₄ and R ₅ are each 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, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl having 2 to 20 C atoms, aryloxycarbonyl having 7 to 20 C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl, Br, F, a cross-linkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

更进一步地，Ar₁选自

Further, Ar ₁ is selected from

Furthermore, Ar ₁ is selected from

In a preferred embodiment, Ar ₁ is selected from any one of the following groups, and the dotted line indicates the connection site:

In a preferred embodiment, Ar ₁ is selected from any one of the following groups:

Among them: The H atoms on the ring can be further substituted.

More preferably, Ar ₁ is selected from any one of the following groups, the H atoms on the ring may be further substituted, and the dotted line indicates the connection site:

In one embodiment, the general formula (1) is selected from the general formula (3-1) or (3-2):

In one embodiment, in the general formula (3-1) or (3-2), V is selected from CR ₁ ; further, R ₁ is selected from H; in one embodiment, in the general formula (3-1) or (3-2), X is selected from CR ₂ ; further, R ₂ is selected from H; in one embodiment, in the general formula (3-1) or (3-2), V is selected from CR ₁ , and X is selected from CR ₂ .

In one embodiment, the general formula (3-1) or (3-2) is selected from the following general formulas:

Among them: The H atoms on the ring can be further substituted.

In one embodiment, the general formula (3-1) is selected from the following general formulas:

Wherein: V, X, X ₁ , R ₃ , R ₄ , L ₁ , L ₂ , and L ₃ are as defined above.

In one embodiment, L ₁ , L ₂ and L ₃ are independently selected from a single bond or any one of the following groups:

in:

Each occurrence _{of X2} is independently selected from _CR6 or N;

Y ₁ is independently selected from NR ₇ , CR ₇ R ₈ , O, S, SiR ₇ R ₈ , S═O, SO ₂ or PR ₇ at each occurrence;

_R6 , _R7 and _R8 are each 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, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl 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, a cross-linkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

In one embodiment, at least one of L ₁ , L ₂ and L ₃ is selected from a single bond; in one embodiment, at least two of L ₁ , L ₂ and L ₃ are selected from a single bond; in one embodiment, L ₁ , L ₂ and L ₃ are all selected from a single bond.

在一实施例中， L₁、L₂和L₃中至少两个

在一实施例中，L₁、L₂和L₃均选自

In one embodiment, at least one of L ₁ , L ₂ and L ₃ is selected from

In one embodiment, at least two of L ₁ , L ₂ and L ₃

In one embodiment, L ₁ , L ₂ and L ₃ are all selected from

在一实施例中，L₁、L₂和L₃中至少两个选自

在一实施例中，L₁、L₂和L₃均选自

In one embodiment, at least one of L ₁ , L ₂ and L ₃ is selected from

In one embodiment, at least two of L ₁ , L ₂ and L ₃ are selected from

In one embodiment, L ₁ , L ₂ and L ₃ are all selected from

在一实施例中，L₁、L₂和L₃中至少一个选自单键且至少一个选自

在一实施例中，L₁、L₂和L₃中一个选自单键，两个选自

在一实施例中，L₁、L₂和L₃中两个选自单键，一个选自

In one embodiment, L ₁ , L ₂ and L ₃ are all selected from a single bond or

In one embodiment, at least one of L ₁ , L ₂ and L ₃ is selected from a single bond and at least one is selected from

In one embodiment, one of L ₁ , L ₂ and L ₃ is selected from a single bond, and two of them are selected from

In one embodiment, two of L ₁ , L ₂ and L ₃ are selected from single bonds, and one is selected from

In one embodiment, the aforementioned X ₂ is selected from CR ₆ ; further, R ₆ is selected from H.

In one embodiment, L ₁ , L ₂ and L ₃ are independently selected from any one of the following groups:

Among them: The H atoms on the ring can be further substituted.

Specifically, L ₁ , L ₂ and L ₃ are independently selected from a single bond or any one of the following groups, and the dotted line indicates the connection site:

Among them: The H atoms on the ring can be further substituted.

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

Wherein: H in the above structure can be further substituted arbitrarily.

According to the organic electroluminescent device of the present invention, the light extraction layer material needs a higher glass transition temperature to improve the thermal stability of the light extraction layer material. In some preferred embodiments, the glass transition temperature Tg ≥ 100 ° C, in a preferred embodiment, Tg ≥ 120 ° C, in a more preferred embodiment, Tg ≥ 140 ° C, in a more preferred embodiment, Tg ≥ 160 ° C, in a most preferred embodiment, Tg ≥ 180 ° C.

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

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

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

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

In certain preferred embodiments, the light extraction layer of the organic electroluminescent device according to the present invention has a large extinction coefficient in the wavelength range of ≤400nm; preferably, the extinction coefficient at a wavelength of 350nm is ≥0.3; preferably ≥0.5, more preferably ≥0.7, and most preferably ≥1.0.

In a preferred embodiment, the organic electroluminescent device according to the present invention includes one or more organic functional layers, and the organic functional layers are selected from one or more layers of an electron injection layer, an electron transport layer, a hole blocking layer, a hole injection layer, a hole transport layer, an electron blocking layer and a light-emitting layer, wherein at least one light-emitting layer is included.

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

In some more preferred embodiments, in the organic electroluminescent device according to the present invention, the organic functional layer is selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

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

The following is a more detailed description of singlet light emitters, triplet light emitters and TADF materials (but not limited to these).

1. Singlet luminophore

Singlet emitters often have longer conjugated π electron systems. To date, there have been many examples, such as styrylamine and its derivatives disclosed in JP2913116B and WO2001021729A1, indenofluorene and its derivatives disclosed in WO2008/006449 and WO2007/140847, and triarylamine derivatives of pyrene disclosed in US7233019 and KR2006-0006760.

In a preferred embodiment, the singlet emitter can be selected from monostyrylamines, distyrylamines, tristyrylamines, tetrastyrylamines, styrylphosphines, styrylethers and aromatic amines.

A monostyrylamine is a compound comprising an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine. A distyrylamine is a compound comprising two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tert-styrylamine is a compound comprising three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A tetrastyrylamine is a compound comprising four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A preferred styrene is diphenylethylene, which may be further substituted. The corresponding phosphines and ethers are defined similarly to the amines. An arylamine or aromatic amine is a compound comprising three unsubstituted or substituted aromatic or heterocyclic ring systems directly attached to the nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably a fused ring system and preferably has at least 14 aromatic ring atoms. Preferred examples are aromatic anthraceneamines, aromatic anthracene diamines, aromatic pyrene amines, aromatic pyrene diamines, aromatic chrysene amines and aromatic chrysene diamines. An aromatic anthraceneamine is a compound wherein one diarylamine group is directly attached to anthracene, preferably at the 9 position. An aromatic anthracenediamine is a compound wherein two diarylamine groups are directly attached to anthracene, preferably at the 9,10 positions. Aromatic pyreneamines, aromatic pyrenediamines, aromatic chryseneamines and aromatic chrysenediamines are similarly defined, wherein the diarylamine groups are preferably attached to the 1 or 1,6 positions of pyrene.

Examples, also preferred examples, of singlet emitters based on vinylamines and aromatic amines can be found in the following patent documents: WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549, WO 2007/115610, US 7250532 B2, DE 102005058557 A1, CN 1583691 A, JP 08053397 A, US 6251531 B1, US 2006/210830 A, EP 1957606 A1 and US 2008/0113101 A1. The entire contents of the above-mentioned patent documents are hereby incorporated herein by reference.

Examples of singlet emitters based on stilbene and its derivatives are disclosed in US Pat. No. 5,121,029.

Further preferred singlet emitters can be selected from indenofluorene-amines and indenofluorene-diamines, as disclosed in WO 2006/122630, benzindenofluorene-amines and benzindenofluorene-diamines, as disclosed in WO 2008/006449, and dibenzoindenofluorene-amines and dibenzoindenofluorene-diamines, as disclosed in WO 2007/140847.

Further preferred singlet emitters can be selected from fluorene-based fused ring systems, such as those disclosed in US2015333277A1, US2016099411A1, and US2016204355A1.

More preferred singlet luminophores can be selected from derivatives of pyrene, such as the structure disclosed in US2013175509A1; triarylamine derivatives of pyrene, such as triarylamine derivatives of pyrene containing dibenzofuran units disclosed in CN102232068B; other triarylamine derivatives of pyrene with specific structures, such as those disclosed in CN105085334A and CN105037173A. Other materials that can be used as singlet luminophores are polycyclic aromatic hydrocarbon compounds, especially derivatives of the following compounds: anthracene such as 9,10-di(2-naphthoanthracene), naphthalene, tetraphenyl, xanthene, phenanthrene, pyrene (such as 2,5,8,11-tetra-t-butylperylene), indenopyrene, phenylene such as (4,4'-bis(9-ethyl-3-carbazole vinyl)-1,1'-biphenyl), diindenopyrene, decacyclic olefins. , hexabenzophenone, fluorene, spirobifluorene, arylpyrene (such as US20060222886), arylene vinyl (such as US5121029, US5130603), cyclopentadiene such as tetraphenylcyclopentadiene, rubrene, coumarin, rhodamine, quinacridone, pyran such as 4 (dicyanomethylene) -6- (4-dimethylaminophenylvinyl-2-methyl) -4H-pyran (DCM), thiopyran, bis (azinyl) imine boron compounds (US 2007/0092753 A1), bis (azinyl) methylene compounds, carbostyryl compounds, oxazinones, benzoxazoles, benzothiazoles, benzimidazoles and dione pyrrolopyrroles. Some materials of singlet luminophores can be found in the following patent documents: US 20070252517 A1, US4769292, US 6020078, US 2007/0252517 A1, US 2007/0252517 A1. The entire contents of the above-listed patent documents are hereby incorporated herein by reference.

The following table lists some examples of suitable singlet emitters:

2. Triplet emitters

Triplet emitters are also called phosphorescent emitters. In a preferred embodiment, the triplet emitter is a metal complex having the general formula M(L)n, wherein M is a metal atom, L can be the same or different each time it appears, is an organic ligand, which is bonded or coordinated to the metal atom M through one or more positions, and n is an integer between 1 and 6. Preferably, the triplet emitter contains a chelating ligand, i.e., a ligand that coordinates to the metal through at least two binding points, and it is particularly preferred that the triplet emitter contains two or three identical or different bidentate or multidentate ligands. Chelating ligands are beneficial to improve the stability of the metal complex. In a preferred embodiment, the metal complex that can be used as a triplet emitter has the following form:

The metal atom M is selected from transition metal elements, lanthanides or actinides, preferably Ir, Pt, Pd, Au, Rh, Ru, Os, Re, Cu, Ag, Ni, Co, W or Eu, especially preferably Ir, Au, Pt, W or Os.

Ar ⁴ and Ar ⁵ may be the same or different each time they appear, and are a cyclic group, wherein Ar ⁴ contains at least one donor atom, i.e. an atom with a lone pair of electrons, such as nitrogen, through which the cyclic group is coordinated to the metal; wherein Ar ⁵ contains at least one carbon atom, through which the cyclic group is connected to the metal; Ar ⁴ and Ar ⁵ are linked together by covalent bonds, and may each carry one or more substituent groups, and they may also be linked together by substituent groups; L' may be the same or different each time they appear, and is a bidentate chelating auxiliary ligand, preferably a monoanionic bidentate chelating ligand; q1 may be 0, 1, 2 or 3, preferably 2 or 3; q2 may be 0, 1, 2 or 3, preferably 1 or 0. Examples of organic ligands may be selected from phenylpyridine derivatives or 7,8-benzoquinoline derivatives. All of these organic ligands may be substituted, for example, by alkyl chains or fluorine or silicon. The auxiliary ligand may be preferably selected from acetic acid acetone or picric acid.

Examples of some triplet emitter materials and their applications can be found in the following patent documents and literature: WO200070655, WO200141512, WO200202714, WO200215645, WO2005033244, WO2005019373, US20050258742, US20070087219, US20070252517, US2008027220, WO2009146770, US20090061681, US20090061681, WO2009118087, WO2010015307, WO2010054731, WO2011157339, WO2012007087, WO201200708, WO2013107487, WO2013094620, WO2013174471, WO 2014031977, WO 2014112450, WO2014007565, WO 2014024131, Baldo et al. Nature (2000), 750, Adachi et al. Appl. Phys. Lett. (2001), 1622, Kido et al. Appl. Phys. Lett. (1994), 2124, Wrighton et al. al.J.Am.Chem.Soc.(1974), 998, Ma et al.Synth.Metals(1998), 245. The entire contents of the above-listed patent documents and literature are hereby incorporated herein by reference. Some examples of suitable triplet luminophores are listed in the following table:

3. Thermally activated delayed fluorescence (TADF)

Traditional organic fluorescent materials can only utilize 25% of the singlet excitons formed by electrical excitation to emit light, and the internal quantum efficiency of the device is low (up to 25%). Although phosphorescent materials can effectively utilize the singlet and triplet excitons formed by electrical excitation to emit light due to the strong spin-orbit coupling of the heavy atom center, the internal quantum efficiency of the device can reach 100%. However, the expensive phosphorescent materials, poor material stability, and serious device efficiency roll-off limit their application in OLEDs. Thermally activated delayed fluorescence luminescent materials are the third generation of organic light-emitting materials developed after organic fluorescent materials and organic phosphorescent materials. This type of material generally has a small singlet-triplet energy level difference (ΔEst), and triplet excitons can be transformed into singlet excitons through anti-intersystem crossing. This can make full use of the singlet and triplet excitons formed under electrical excitation. The internal quantum efficiency of 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 required, and the application prospects in the field of OLED are broad.

TADF materials need to have a small singlet-triplet energy level difference, preferably ΔEst < 0.3 eV, second preferably ΔEst < 0.2 eV, and most preferably ΔEst < 0.1 eV. In a preferred embodiment, TADF materials have a relatively small ΔEst. In another preferred embodiment, TADF has a better fluorescence quantum efficiency. Some TADF luminescent materials can be found in the following patent documents: CN103483332 (A), TW201309696 (A), TW201343874 (A), TW201350558 (A), US20120217869 (A1), WO2013133359 (A1), WO2013154064 (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, Adachi, et al. Chem. Commun., 48, 2012, 11392, Adachi, et.al.Nature Photonics, 6, 2012, 253, Adachi, et.al.Nature, 492, 2012, 234, Adachi, et.al.J.Am.Chem.Soc, 134, 2012, 14706, Adachi, et.al.Angew.Chem.Int.Ed, 51, 2012, 1 1311, Adachi, et.al.Chem.Commun., 48, 2012, 9580, Adachi, et.al.Chem.Commun., 48, 2013, 10385, Adachi, et.al.Adv.Mater., 25, 2013, 3319, Adachi, et.al.Chem.Mater., 25, 2013, 3038, Adachi, et.al.Chem.Mater., 25, 2013, 3766, Adachi, et.al.J.Mater.Chem.C., 1, 2013, 4599, Adachi, et.al.J.Phys.Chem.A., 117, 2013, 5607, the entire contents of the above-listed patents or article documents are hereby incorporated herein by reference.

Some examples of suitable TADF emitters are listed below:

The device structure of the organic light emitting diode, including the cathode, the anode and the light extraction layer, is described below, but is not limited thereto.

The anode may comprise 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 light-emitting body in the light-emitting layer or the p-type semiconductor material as the HIL or HTL or the electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, and 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), etc. Other suitable anode materials are known and can be easily selected for use by ordinary technicians in this field. 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, electron beam (e-beam), etc. In some embodiments, the anode is patterned. 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 energy level or conduction band energy level of the luminophore in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or the electron transport layer (ETL) or the hole blocking layer (HBL) is less than 0.5 eV, preferably less than 0.3 eV, and most preferably less than 0.2 eV. In principle, all materials that can be used as cathodes of OLEDs may be used as cathode materials of the device of the present invention. Examples of cathode materials include but are not limited to: Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, _BaF2 /Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. 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, electron beam (e-beam), etc.

The light extraction layer material needs to have a suitable energy level structure, with strong absorption in the region with a wavelength less than 400nm, and weak or close to zero absorption of visible light with a wavelength greater than 400nm, to prevent the internal materials of the device from being damaged by high-energy light in subsequent processes. At the same time, the light extraction layer material has a high refractive index, which can be used to beneficially guide the emission of visible light and improve the luminous efficiency of organic electronic light-emitting devices. When the reflectivity of the interface between the light extraction layer material and the adjacent electrode is large, the influence of light interference is large. Therefore, the refractive index of the light extraction layer material is preferably greater than the refractive index of the adjacent electrode, and the refractive index at 630nm is 1.50 or more, more preferably 1.70 or more, and particularly preferably 1.80 or more.

In some more preferred 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, preferably 20 nm to 150 nm, more preferably 30 nm to 100 nm, and most preferably 40 nm to 90 nm.

In some embodiments, the light extraction layer is disposed on the cathode surface and away from the organic functional layer. In other embodiments, the light extraction layer is disposed on the anode surface and away from the organic functional layer.

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

The present invention further relates to an organic compound selected from the structure shown in the general formula (4):

in:

_L1 and _L3 are independently selected from a single bond, a substituted or unsubstituted aromatic group or heteroaromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring system having 3 to 30 ring atoms;

_L2 is selected from a single bond or the following groups:

W, _W1 each occur independently selected from _CR9 or N;

Y ₂ and Y ₃ are each independently selected from NR ₁₀ , CR ₁₀ R ₁₁ , O, S, SiR ₁₀ R ₁₁ , S═O, SO ₂ or PR ₁₀ ;

_R9 , _R10 and _R11 are each 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, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl 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, a cross-linkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

中至少一个W选自N。进一步地，

选自

更进一步，

选自

虚线表示连接位点。In one embodiment,

At least one W is selected from N. Further,

Selected from

Going further,

Selected from

Dashed lines indicate ligation sites.

中W每次出现分别独立选自CR₉。In one embodiment,

Each occurrence of W is independently selected from CR ₉ .

选自以下基团中的任一种，虚线表示连接位点：further,

Select any one of the following groups, the dotted line indicates the attachment site:

选自以下基团中的任一种，环上的H原子可以进一步被取代，虚线表示连接位点：In one embodiment,

Selected from any of the following groups, the H atoms on the ring can be further substituted, and the dotted line indicates the connection site:

In one embodiment, the general formula (4) is selected from any one of the general formulas (5-1) to (5-6):

More preferably, W in the general formulae (5-1) to (5-6) is selected from CR ₉ ; even more preferably, R ₉ is selected from H.

In one embodiment, _L2 is selected from a single bond or any one of the following groups:

在一实施例中，L₂选自单键或者

在一实施例中，L₂选自单键或苯；在一实施例中，L₂选自单键。In one embodiment, _L2 is selected from a single bond or

In one embodiment, _L2 is selected from a single bond or

In one embodiment, L ₂ is selected from a single bond or benzene; in one embodiment, L ₂ is selected from a single bond.

In one embodiment, _L1 and _L3 are independently selected from a single bond or any one of the following groups:

in:

Each occurrence _{of X2} is independently selected from _CR6 or N;

Y ₁ is independently selected from NR ₇ , CR ₇ R ₈ , O, S, SiR ₇ R ₈ , S═O, SO ₂ or PR ₇ at each occurrence;

_R6 , _R7 and _R8 are each 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, linear thioalkoxy having 1 to 20 C atoms, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, branched or cyclic thioalkoxy having 3 to 20 C atoms, silyl, keto having 1 to 20 C atoms, alkoxycarbonyl 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, a cross-linkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

In one embodiment, _L1 and _L3 are independently selected from any one of the following groups:

Among them: The H atoms on the ring can be further substituted.

Specifically, L ₁ , L ₂ and L ₃ are independently selected from a single bond or any one of the following groups, and the dotted line indicates the connection site:

Among them: The H atoms on the ring can be further substituted.

In one embodiment, at least one of L ₁ , L ₂ and L ₃ is selected from a single bond; in one embodiment, at least two of L ₁ , L ₂ and L ₃ are selected from a single bond; in one embodiment, L ₁ , L ₂ and L ₃ are all selected from a single bond. In one embodiment, L ₁ is a single bond; in one embodiment, L ₃ is a single bond; in one embodiment, L ₁ and L ₃ are single bonds;

In one embodiment, at least one of L ₁ , L ₂ and L ₃ is selected from benzene or naphthalene; in one embodiment, at least two of L ₁ , L ₂ and L ₃ are selected from benzene or naphthalene; in one embodiment, L ₁ , L ₂ and L ₃ are all selected from benzene or naphthalene.

In one embodiment, at least one of L ₁ , L ₂ and L ₃ is selected from benzene; in one embodiment, at least two of L ₁ , L ₂ and L ₃ are benzene; in one embodiment, L ₁ , L ₂ and L ₃ are all selected from benzene. In one embodiment, L ₃ is benzene; in one embodiment, L ₂ is benzene; in one embodiment, L ₁ and L ₃ are benzene.

In one embodiment, L ₁ , L ₂ and L ₃ are all selected from a single bond or benzene; more preferably, at least one is selected from a single bond and at least one is selected from benzene; more preferably, one is selected from a single bond and two are selected from benzene; more preferably, two are selected from a single bond and one is selected from benzene. In one embodiment, L ₁ and L ₃ are single bonds, and L ₂ is benzene.

Specifically, the organic compound according to the present invention is selected from any one of the structural formulas (G-145) to (G-211) as described above, but is not limited thereto.

The organic compound described in the present invention can be used not only in the light extraction layer of organic electronic devices, but also in other organic functional layers, such as electron injection layer, electron transport layer, hole injection layer, hole transport layer and light-emitting layer.

A light extraction layer material comprises the organic compound as described above.

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

In certain embodiments, the organic compound according to the present invention has a molecular weight of ≤1200 g/mol, preferably ≤1100 g/mol, very preferably ≤1000 g/mol, more preferably ≤950 g/mol, and most preferably ≤900 g/mol.

The present invention also relates to a composition comprising at least one organic compound as represented by the general formula (4) above, and at least one organic solvent; the at least one organic solvent is selected from aromatic hydrocarbons or heteroaromatics, esters, aromatic ketones or aromatic ethers, aliphatic ketones or aliphatic ethers, alicyclic or olefin compounds, or borate or phosphate compounds, or a mixture of two or more solvents.

The present 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 can be selected from, but not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell, an organic light emitting cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spin electronic device, an organic sensor and an organic plasmon emission diode, etc., and is particularly preferably an OLED.

The present invention will be described below in conjunction with preferred embodiments, but the present invention is not limited to the following embodiments. It should be understood that the attached claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should be aware that certain changes made to the various embodiments of the present invention will be covered by the spirit and scope of the claims of the present invention.

Specific embodiments

The synthesis methods of the compounds of the present invention are exemplified, but the present invention is not limited to the following examples.

Synthesis of compound C-1:

Compound 1-1 (4.86 g, 15 mmol), 1-2 (8.16 g, 30 mmol), potassium carbonate (6.26 g, 45 mmol), tetrakis(triphenylphosphine)palladium (0.52 g, 0.45 mmol) were placed in a three-necked flask with toluene and methanol (volume ratio 3:1), nitrogen was replaced three times, the temperature was gradually raised to 80°C, and the reaction was stirred. When the TLC spot plate reactant disappeared, the heat source was removed. After the system was cooled, water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 4.19 g of compound I-3, with a yield of 45%.

Dissolve compound 1-3 (3.73 g, 6 mmol) in anhydrous toluene, add 1-4 (0.92 g, 6 mmol), sodium tert-butoxide (1.73 g, 18 mmol) and tris dibenzylideneacetone palladium (0.16 g, 0.18 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.18 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 2.88 g of compound C-1, with a yield of 65%. m/z = 738.6

Synthesis of compound C-2:

Dissolve compound 2-1 (2.6 g, 9.7 mmol) and 2-2 (7.7 g, 25.2 mmol) in 100 mL of anhydrous toluene, add sodium tert-butoxide (4.8 g, 50 mmol) and tridibenzylideneacetone dipalladium (0.28 g, 0.3 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.3 mmol), gradually raise the temperature to 80 ° C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 5.6 g of compound C-2 with a yield of 72%. m/z = 678.5

Synthesis of compound C-3:

Dissolve compound 3-1 (3.1 g, 10.9 mmol) and 2-2 (7.3 g, 24 mmol) in anhydrous toluene, sodium tert-butoxide (4.8 g, 50 mmol) and tris dibenzylideneacetone dipalladium (0.28 g, 0.3 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.3 mmol), gradually raise the temperature to 80 ° C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 4.2 g of compound C-3, with a yield of 53%. m/z = 737.3

Synthesis of compound C-4:

4-1 (10 g, 58 mmol) and 4-2 (8.9 g, 58 mmol) were placed in polyphosphoric acid, heated to 160°C, and stirred for about 12 hours. After cooling to room temperature, sodium hydroxide aqueous solution was added at low temperature for neutralization, and the intermediate 4-3 was obtained by vacuum filtration with a total of 14.3 g, with a yield of 85%.

Dissolve the intermediate 4-3 (14.3 g, 9.7 mmol) in a 100 mL mixed solution of tetrahydrofuran and methanol, add 3 times the amount of selenium chloride dihydrate (6.75 g, 30 mmol), and heat to 70°C. Stir the reaction for 12 hours, add sodium bicarbonate aqueous solution after the system is cooled, extract with ethyl acetate, combine the organic phases, and dry over anhydrous sodium sulfate. Concentrate under reduced pressure through a silica gel column to obtain 9.5 g of intermediate 4-4, with a yield of 74%.

Dissolve intermediate 4-4 (5 g, 19.2 mmol) and 2-2 (12.8 g, 42 mmol) in 80 mL of anhydrous toluene, sodium tert-butoxide (5.8 g, 60 mmol) and tris dibenzylideneacetone dipalladium (0.55 g, 0.6 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.6 mmol), gradually raise the temperature to 80 ° C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 6.2 g of compound C-4, with a yield of 45%. m/z = 712.5

Synthesis of compound C-5:

9-Phenanthrene boronic acid (13g, 58.5mmol), p-bromoaniline (10g, 58.5mmol), potassium carbonate (73g, 175mmol), tetrakis(triphenylphosphine)palladium (2g, 1.76mmol) were placed in a three-necked flask with toluene and methanol (volume ratio 3:1), nitrogen was replaced three times, the temperature was gradually raised to 80°C, and the reaction was stirred. When the TLC spot plate reactant disappeared, the heat source was removed. After the system was cooled, water was added, the organic layer was separated, and it was extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain a total of 13.5g of intermediate 5-1 with a yield of 86%.

Dissolve compound 5-1 (10 g, 37.1 mmol) and 2-2 (11.35 g, 37.1 mmol) in anhydrous toluene, add sodium tert-butoxide (10.7 g, 111 mmol) and tris dibenzylideneacetone dipalladium (1 g, 1.11 mmol), replace nitrogen three times, add tri-tert-butylphosphine (1.11 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain a total of 10.3 g of intermediate 5-2 with a yield of 56%.

Dissolve compound 5-2 (8 g, 16.2 mmol) and 5-3 (3.8 g, 16.2 mmol) in anhydrous toluene, add sodium tert-butoxide (4.7 g, 48.6 mmol) and tris dibenzylideneacetone palladium (0.41 g, 0.5 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.5 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 8.2 g of compound C-5, with a total yield of 78%. m/z = 648.9

Synthesis of compound C-6:

Dissolve compound 6-1 (8 g, 36.4 mmol) and 6-2 (14.3 g, 36.4 mmol) in anhydrous toluene, add sodium tert-butoxide (10.5 g, 109 mmol) and tris dibenzylideneacetone dipalladium (1 g, 1.1 mmol), replace nitrogen three times, add tri-tert-butylphosphine (1.1 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 9.2 g of intermediate 6-3, with a yield of 47%.

Dissolve compound 6-3 (6 g, 11.2 mmol) and 2-2 (3.43 g, 11.2 mmol) in anhydrous toluene, add sodium tert-butoxide (3.3 g, 33.6 mmol) and tris dibenzylideneacetone dipalladium (0.31 g, 0.34 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.34 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 6.6 g of compound C-6, with a yield of 77%. m/z = 761.2

Synthesis of compound C-7:

Dissolve compound 7-1 (1.7 g, 6.1 mmol) and 5-2 (3 g, 6.1 mmol) in anhydrous toluene, add sodium tert-butoxide (1.76 g, 18.3 mmol) and tris dibenzylideneacetone dipalladium (0.17 g, 0.18 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.18 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 3.6 g of compound C-7, with a yield of 86%. m/z = 688.7

Synthesis of compound C-8:

Dissolve compound 8-1 (2.9 g, 20 mmol) and 2-2 (6.12 g, 20 mmol) in anhydrous toluene, add sodium tert-butoxide (5.76 g, 60 mmol) and tris dibenzylideneacetone dipalladium (0.55 g, 0.6 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.6 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 4.58 g of intermediate 8-2, with a yield of 62%.

Dissolve the intermediate 8-3 (3.79 g, 12 mmol) and 8-2 (4.43 g, 12 mmol) in anhydrous toluene, add sodium tert-butoxide (3.46 g, 36 mmol) and tris dibenzylideneacetone palladium (0.33 g, 0.36 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.36 mmol), gradually raise the temperature to 80 ° C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 5.37 g of compound C-8, with a yield of 69%. m/z = 649.9

Synthesis of compound C-9:

Dissolve compound 9-1 (2.89 g, 10 mmol) and 5-2 (4.95 g, 10 mmol) in anhydrous toluene, add sodium tert-butoxide (2.88 g, 30 mmol) and tris dibenzylideneacetone dipalladium (0.28 g, 0.3 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.3 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through silica gel to obtain 5.98 g of compound C-9, with a yield of 85%. m/z = 704.6

Synthesis of compound C-10:

Dissolve compound 10-1 (2.38 g, 8 mmol) and 2-2 (5.51 g, 18 mmol) in anhydrous toluene, add sodium tert-butoxide (2.3 g, 24 mmol) and tridibenzylideneacetone dipalladium (0.22 g, 0.24 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.24 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 3.30 g of compound C-10, with a yield of 55%. m/z = 749.7

Synthesis of compound C-11:

Dissolve compound 11-1 (4.79 g, 15 mmol) and 2-2 (4.59 g, 15 mmol) in anhydrous toluene, add sodium tert-butoxide (4.32 g, 45 mmol) and tris dibenzylideneacetone dipalladium (0.41 g, 0.45 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.45 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 4.74 g of intermediate 11-2, with a yield of 58%.

Dissolve the intermediate 11-2 (4.36 g, 8 mmol) and 11-3 (1.82 g, 8 mmol) in anhydrous toluene, add sodium tert-butoxide (2.30 g, 24 mmol) and tris dibenzylideneacetone dipalladium (0.22 g, 0.24 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.24 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 2.65 g of compound C-11, with a yield of 45%. m/z = 737.7

Synthesis of compound C-12:

Dissolve the intermediate 11-2 (4.36 g, 8 mmol) and 12-1 (2.32 g, 8 mmol) in anhydrous toluene, add sodium tert-butoxide (2.30 g, 24 mmol) and tris dibenzylideneacetone dipalladium (0.22 g, 0.24 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.24 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 4.58 g of compound C-12, with a yield of 76%. m/z = 754.5

Synthesis of compound C-13:

Compound 1-1 (6.5 g, 20 mmol), 13-1 (10.88 g, 40 mmol), potassium carbonate (8.34 g, 60 mmol), tetrakis(triphenylphosphine)palladium (0.69 g, 0.6 mmol) were placed in a three-necked flask with toluene and methanol (volume ratio 3:1), nitrogen was replaced three times, the temperature was gradually raised to 80°C, and the reaction was stirred. When the TLC spot plate reactant disappeared, the heat source was removed. After the system was cooled, water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 9.44 g of intermediate 13-2, with a yield of 76%.

Dissolve compound 13-2 (6.21 g, 10 mmol) in anhydrous toluene, add 7-1 (2.73 g, 10 mmol), sodium tert-butoxide (2.88 g, 30 mmol) and tris dibenzylideneacetone dipalladium (0.28 g, 0.3 mmol), replace nitrogen three times, add tri-tert-butylphosphine (0.3 mmol), gradually raise the temperature to 80°C, and stir to react. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 5.54 g of compound C-13, with a yield of 68%. m/z = 814.3

Synthesis of compound C-14:

Compound 14-1 (2.1 g, 10 mmol) and 2-bromotriphenylene (3.06 g, 10 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (2.88 g, 30 mmol) and tris dibenzylideneacetone dipalladium (92 mg, 0.1 mmol), and nitrogen was replaced three times, and tri-tert-butylphosphine (0.1 mmol) was added, and the temperature was gradually raised to 80°C, and the reaction was stirred. When the TLC spot plate reactant disappeared, the heat source was removed. After the system was cooled, water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 2.7 g of compound 14-2, with a yield of 62%.

Compound 14-2 (2.6 g, 6 mmol), 3-bromo-1,10-phenanthroline (1.55 g, 6 mmol), dissolved in anhydrous toluene, sodium tert-butoxide (1.73 g, 18 mmol) and tridibenzylideneacetone dipalladium (55 mg, 0.06 mmol), replaced nitrogen three times, added tri-tert-butylphosphine (0.06 mmol), gradually heated to 110 ° C, stirred for reaction. When the TLC spot plate reactant disappears, remove the heat source. After the system is cooled, add water, separate the organic layer, and extract it with ethyl acetate three times, concentrate under reduced pressure, and pass through a silica gel column to obtain 1.7 g of compound C-14, with a yield of 46%. m/z = 615.2

Synthesis of compound C-15:

Compound 15-1 (3.3 g, 15 mmol) and 2-bromotriphenylene (4.6 g, 15 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (4.32 g, 45 mmol) and tris dibenzylideneacetone dipalladium (0.14 g, 0.15 mmol), and nitrogen was replaced three times, and tri-tert-butylphosphine (0.15 mmol) was added, and the temperature was gradually raised to 80°C, and the reaction was stirred. When the TLC spot plate reactant disappeared, the heat source was removed. After the system was cooled, water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and passed through a silica gel column to obtain 4.74 g of compound 15-2, with a yield of 71%.

Compound 15-2 (4.45 g, 10 mmol) and 15-3 (2.75 g, 10 mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (2.88 g, 30 mmol) and tris dibenzylideneacetone dipalladium (92 mg, 0.1 mmol), and nitrogen was replaced three times, and tri-tert-butylphosphine (0.01 mmol) was added, and the temperature was gradually raised to 110°C, and the reaction was stirred. When the TLC spot plate reactant disappeared, the heat source was removed. After the system was cooled, water was added, the organic layer was separated, and extracted with ethyl acetate three times, concentrated under reduced pressure, and 2.43 g of compound C-15 was passed through a silica gel column, with a yield of 38%. m/z = 641.2

Extinction system and refractive index calculation

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

The results are shown in Table 1:

Table 1

The compound of the present invention has weak absorption in the visible light band and high absorption in the ultraviolet band, and can resist the damage of external high-energy light to the inside of the device. The higher refractive index can ensure better light extraction effect.

Preparation and characterization of OLED devices

The preparation process of the OLED device described above is described in detail below through a specific embodiment. As shown in FIG1 , 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:

在空穴注入层上，通过真空蒸镀方式蒸镀空穴传输材料SFNFB，厚度为80nm。在空穴传输层之上蒸镀发光层，m-CP作为作为主体材料，Ir(p-ppy)₃作为掺杂材料，Ir(p-ppy)₃和m-CP 的质量比为1:9，厚度为30nm。在发光层之上，通过真空蒸镀方式蒸镀电子传输材料NaTzF₂，厚度为30 nm。在电子传输层之上，真空蒸镀电子注入层LiF，厚度为1nm，该层为电子注入层7。在电子注入层之上，真空蒸镀阴极Mg:Ag层，Mg:Ag掺杂比例为9:1，厚度15nm。在阴极层之上，通过真空蒸镀方式蒸镀光取出层化合物C-2，厚度为60nm。The ITO conductive glass anode layer was cleaned, then ultrasonically cleaned with deionized water, acetone, and isopropanol 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 was evaporated by vacuum evaporation with a thickness of 5nm and an evaporation rate of

On the hole injection layer, the hole transport material SFNFB is vacuum deposited with a thickness of 80nm. On the hole transport layer, the light-emitting layer is deposited, with m-CP as the main material and Ir(p-ppy) ₃ as the doping material. The mass ratio of Ir(p-ppy) ₃ and m-CP is 1:9, and the thickness is 30nm. On the light-emitting layer, the electron transport material NaTzF ₂ is vacuum deposited with a thickness of 30nm. On the electron transport layer, the electron injection layer LiF is vacuum deposited with a thickness of 1nm. This layer is the electron injection layer 7. On the electron injection layer, the cathode Mg:Ag layer is vacuum deposited with a Mg:Ag doping ratio of 9:1 and a thickness of 15nm. On the cathode layer, the light extraction layer compound C-2 is vacuum deposited with a thickness of 60nm.

Device Example 2: The compound of the light extraction layer of the organic electroluminescent device is changed to C-3.

Device Example 3: The compound of the light extraction layer of the organic electroluminescent device is changed to C-6.

Device Example 4: The compound of the light extraction layer of the organic electroluminescent device is changed to C-7.

Device Example 5: The compound of the light extraction layer of the organic electroluminescent device is changed to C-9.

Device Example 6: The compound of the light extraction layer of the organic electroluminescent device is changed to C-10.

Device Example 7: The compound of the light extraction layer of the organic electroluminescent device is changed to C-11.

Device Example 8: The compound of the light extraction layer of the organic electroluminescent device is changed to C-12.

Device Example 9: The compound of the light extraction layer of the organic electroluminescent device is changed to C-13.

Device Example 10: The compound of the light extraction layer of the organic electroluminescent device is changed to C-1.

Device Example 11: The compound of the light extraction layer of the organic electroluminescent device is changed to C-4.

Device Example 12: The compound of the light extraction layer of the organic electroluminescent device is changed to C-5.

Device Example 13: The compound of the light extraction layer of the organic electroluminescent device is changed to C-8.

Device Example 14: The compound of the light extraction layer of the organic electroluminescent device is changed to C-14.

Device Example 15: The compound of the light extraction layer of the organic electroluminescent device is changed to C-15.

Device Comparative Example 1: The compound of the light extraction layer of the organic electroluminescent device is changed to CBP.

The structures of the compounds involved in the device are as follows:

Table 2

serial number Light extraction layer compound Luminous efficiency (cd/A) Device Example 1 C-2 1.24 Device Example 2 C-3 1.12 Device Example 3 C-6 1.09 Device Example 4 C-7 1.25 Device Example 5 C-9 1.15 Device Example 6 C-10 1.09 Device Example 7 C-11 1.05 Device Example 8 C-12 1.17 Device Example 9 C-13 1.21 Device Example 10 C-1 1.12 Device Example 11 C-4 1.13 Device Example 12 C-5 1.04 Device Example 13 C-8 1.06 Device Example 14 C-14 1.11 Device Example 15 C-15 1.12 Comparative Example 1 CBP 1

The luminous efficiency in Table 2 is a relative value obtained when the current density is 10 mA/cm ^2. It can be seen from Table 2 that compared with the comparative example, the compounds of the present invention as a light extraction layer can effectively improve the luminous efficiency of the organic electroluminescent device. Furthermore, the luminous efficiency of the organic electroluminescent device using C-2, C-7, C-12, and C-13 as the light extraction layer of the compounds of the present invention is better.

The above-mentioned embodiments only express several implementation methods of the present invention, and the description thereof is relatively specific and detailed, but it cannot be understood as limiting the scope of the invention patent. It should be pointed out that for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, which all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be based on the attached claims.

Claims (10)

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 a surface of one of the electrodes and on a side away from the organic functional layer, characterized in that: the light extraction layer material contains a compound represented by general formula (1):

wherein:

L ₁ 、L ₂ and L ₃ Each independently selected from single bond, substituted or unsubstituted ringAn aromatic or heteroaromatic group of atoms 5 to 30, or a substituted or unsubstituted non-aromatic ring system of ring atoms 3 to 30;

Ar ₁ one selected from the following electron withdrawing groups:

wherein, X ₁ Each occurrence is independently selected from CR ₃ Or N, and at least one X ₁ Is selected from N, R ₃ And R ₄ Each occurrence is independently selected from: hydrogen, D, straight-chain alkyl having 1 to 20C atoms, straight-chain alkoxy having 1 to 20C atoms, straight-chain thioalkoxy having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ Cl, br, F, a crosslinkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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;

Ar ₂ selected from substituted or unsubstituted condensed ring aromatic group or condensed ring hetero aromatic group with 10-30 ring atoms;

v is independently selected from CR at each occurrence ₁ Or N;

R ₁ each occurrence is independently selected from: hydrogen, D, a straight-chain alkyl group having 1 to 20C atoms, a straight-chain alkoxy group having 1 to 20C atoms, a straight-chain thioalkoxy group having 1 to 20C atoms, a branched or cyclic alkyl group having 3 to 20C atoms, a branched or cyclic alkoxy group having 3 to 20C atoms,branched or cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxy, nitro, CF ₃ Cl, br, F, a crosslinkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

2. The organic electroluminescent device according to claim 1, wherein: the general formula (1) is selected from general formula (3-1) or (3-2):

wherein:

x is independently selected from CR at each occurrence ₂ Or N;

R ₂ each occurrence is independently selected from: hydrogen, D, straight-chain alkyl having 1 to 20C atoms, straight-chain alkoxy having 1 to 20C atoms, straight-chain thioalkoxy having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ 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, aryloxy groups having 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups having 5 to 60 ring atomsHeteroaryloxy groups of ring atoms, or combinations of these groups.

3. The organic electroluminescent device according to claim 1, wherein L ₁ 、L ₂ And L ₃ Each independently selected from a single bond or any of the following groups:

wherein:

X ₂ each occurrence is independently selected from CR ₆ Or N;

Y ₁ each occurrence is independently selected from NR ₇ 、CR ₇ R ₈ 、O、S、SiR ₇ R ₈ 、S＝O、SO ₂ Or PR ₇ ；

R ₆ 、R ₇ And R ₈ Each occurrence is independently selected from: hydrogen, D, straight-chain alkyl having 1 to 20C atoms, straight-chain alkoxy having 1 to 20C atoms, straight-chain thioalkoxy having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ Cl, br, F, a crosslinkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

4. The organic electroluminescent device according to claim 3, wherein L ₁ 、L ₂ And L ₃ Are respectively provided withIndependently selected from single bonds or benzene.

5. The organic electroluminescent device according to any one of claims 1 to 4, wherein: the refractive index of the material of the light extraction layer at the wavelength of 630nm is greater than 1.7; and/or

The extinction coefficient of the material of the light extraction layer is less than 0.1 at a wavelength of 430 nm.

6. The organic electroluminescent device according to any one of claims 1 to 4, 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.

7. An organic compound characterized by: selected from the structures represented by the general formula (4):

wherein:

L ₁ and L ₃ Each independently selected from a single bond, a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 30 ring atoms, or a substituted or unsubstituted non-aromatic ring system having 3 to 30 ring atoms;

L ₂ selected from a single bond or any of the following groups:

W、W ₁ each occurrence is independently selected from CR ₉ Or N;

Y ₂ 、Y ₃ each occurrence is independently selected from NR ₁₀ 、CR ₁₀ R ₁₁ 、O、S、SiR ₁₀ R ₁₁ 、S＝O、SO ₂ Or PR ₁₀ ；

R ₉ 、R ₁₀ And R ₁₁ Each occurrence is independently selected from: hydrogen, D, straight-chain alkyl having 1 to 20C atoms, straight-chain alkoxy having 1 to 20C atoms, straight-chain thioalkoxy having 1 to 20C atoms, branched or cyclic alkyl having 3 to 20C atoms, branched or cyclic alkoxy having 3 to 20C atoms, branched or cyclic thioalkoxy having 3 to 20C atoms, silyl, keto having 1 to 20C atoms, alkoxycarbonyl having 2 to 20C atoms, aryloxycarbonyl having 7 to 20C atoms, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF, having 1 to 20C atoms ₃ Cl, br, F, a crosslinkable group, a substituted or unsubstituted aromatic group having 5 to 60 ring atoms, a substituted or unsubstituted heteroaromatic group 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.

8. The organic compound of claim 7, wherein: the general formula (4) is selected from any one of general formulae (5-1) to (5-6):

9. a composition comprising at least one organic compound according to any one of claims 7 to 8, and at least one organic solvent.

10. A light extraction layer material comprising the organic compound according to any one of claims 7 to 8.

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