WO2021143246A1 - Organic electroluminescent device and fused ring-based aromatic amine compounds - Google Patents

Abstract

An organic electroluminescent device and fused ring-based aromatic amine compounds. The organic electroluminescent device comprises 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, wherein the material of the light extraction layer comprises a compound having the structure of general formula (1). The material of the light extraction layer has a higher extinction coefficient in an ultraviolet region, and has a higher refractive index in a visible light region, so that the material can reduce the damage of external high-energy light to the internal material of the organic electroluminescent display device, and is applied to the organic electroluminescent device to improve the light extraction efficiency and the light emission efficiency of the device.

Description

Organic electroluminescence device and aromatic amine compound containing fused ring Technical field

The invention relates to the technical field of organic electroluminescence, in particular to an organic electroluminescence device and an aromatic amine compound containing a condensed ring, in particular to an organic electroluminescence device, an aromatic amine compound containing a condensed ring, and a composition , Light extraction layer material.

Background technique

Organic electroluminescence display equipment is a type of self-luminous display device, which generates excitons through the transfer and recombination of carriers between various functional layers, and emits light by relying on 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 electroluminescent diodes (OLED) has been greatly improved, but its internal quantum efficiency has approached the theoretical limit. Therefore, improving the light extraction efficiency becomes an effective means to further improve the stability and current efficiency of the device (such as the accumulation of metal complexes in the emitting layer, the matching of refractive indexes between functional layers, etc.).

In recent years, in order to improve the light extraction efficiency, it has been proposed to provide a light extraction layer outside the translucent electrode with a low refractive index. For example, in 2001, Hung et al. covered the surface of a metal cathode with a layer of about 50nm of organic or inorganic compounds to improve 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, using the difference in refractive index between functional layers to improve light extraction efficiency, but was limited by the evaporation of inorganic materials. For reasons such as high temperature and slow evaporation rate, these compounds have not been used more in organic electroluminescent devices.

Therefore, a new class of materials that can 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 purpose 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 organic electroluminescence devices.

The present invention attempts to use organic compounds with higher refractive index in electroluminescent devices to improve light extraction efficiency. Such compounds need to meet the following types of conditions: high extinction coefficient in the ultraviolet band (<400nm) to avoid adverse effects of harmful light on the device materials; in the visible light range (>430nm), the extinction coefficient is close to 0, which has a higher effect on visible light. Transmittance reduces the impact on the light output efficiency of the device; it has a higher refractive index in the visible light range and has a small difference, which has the characteristics of improving light output and optimizing the structure of the device; it has a higher glass transition temperature and thermal decomposition temperature.

The technical scheme of the present invention is as follows:

An organic electroluminescence device comprising 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, It is characterized in that: the material of the light extraction layer contains a compound having a structure as shown in the general formula (1):

in:

Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from single bonds, substituted or unsubstituted aromatic groups with 5 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms. Group, or substituted or unsubstituted non-aromatic ring system group with 3 to 30 ring atoms;

Ar _{1 is} selected from electron withdrawing groups;

Ar _{2 is} selected from any group in (A-1)-(A-4):

Each time X appears, it is independently selected from CR ₁ or N;

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

The present invention further relates to a condensed ring-containing aromatic amine compound, which is characterized in that it has a structure as shown in the general formula (5):

in:

Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from single bonds, substituted or unsubstituted aromatic groups with 5 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms Group, or substituted or unsubstituted non-aromatic ring system group with 3 to 30 ring atoms;

Each time X appears, it is independently selected from CR ₁ or N;

Each time X ₁ appears, it is independently selected from CR ₂ or N, and at least one X _{1 is} selected from N;

Each time Y appears, it is independently selected from NR ₃ , CR ₃ R ₄ , O, S, SiR ₃ R ₄ , S=O, SO ₂ or P(R ₃ );

Each occurrence of R ₁ -R ₄ is independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 A ring atom aryloxy group, 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 of the above-mentioned condensed ring-containing aromatic amine compounds and at least one organic solvent.

The present invention relates to a light extraction layer material comprising the above-mentioned fused ring-containing aromatic amine compound.

Beneficial effects:

The material of the light extraction layer of the present invention has a higher glass transition temperature, a higher thermal stability of the compound, and a high extinction coefficient in the ultraviolet band (<400nm), which can avoid the adverse effect of harmful light on the device material; The range (>430nm) has a small extinction coefficient, which has a high transmittance to visible light, which reduces the impact on the light output efficiency of the device; and has a higher refractive index in the visible light range with small differences, and a higher glass transition temperature And thermal decomposition temperature. When used in an organic electroluminescent device, it can avoid harmful light's adverse effects on the internal materials of the device, improve the visible light extraction efficiency of the device, and optimize the device structure.

Description of the drawings

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), and 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;

Detailed ways

The invention provides an organic electroluminescence device and an aromatic amine compound containing a condensed ring. In order to make the objectives, technical solutions, and effects of the present invention clearer and clearer, the present invention will be described in further detail below. It should be understood that the specific embodiments described here are only used to explain the present invention, but not used to limit the present invention.

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

In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be understood to be optionally substituted by a group acceptable in the art, including but not limited to: C _1-30 alkyl, cycloalkyl containing 3-20 ring atoms, Heterocyclic groups with 3-20 ring atoms, aryl groups with 5-20 ring atoms, heteroaryl groups with 5-20 ring atoms, silyl groups, carbonyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, amino groups Formyl, haloformyl, formyl, -NRR', cyano, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, nitro or halogen, and The above-mentioned groups can also be further substituted with substituents acceptable in the art; it is understandable 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 group, cycloalkyl group containing 3-8 ring atoms, heterocyclic group containing 3-8 ring atoms, aryl group containing 5-20 ring atoms or heteroaromatic group containing 5-10 ring atoms Group; the C _1-6 alkyl group, cycloalkyl group containing 3-8 ring atoms, heterocyclic group containing 3-8 ring atoms, aryl group containing 5-20 ring atoms or 5-10 The heteroaryl group of one ring atom is optionally further substituted by one or more of the following groups: C _1-6 alkyl group, cycloalkyl group containing 3-8 ring atoms, heterocyclic group containing 3-8 ring atoms , Halogen, hydroxyl, nitro or amino.

In the present invention, "the number of ring atoms" means the number of structural compounds (for example, monocyclic compounds, condensed ring compounds, cross-linked compounds, carbocyclic compounds, heterocyclic compounds) obtained by synthesizing a cyclic atom bond to form the ring itself The number of atoms among atoms. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.

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

The aromatic group refers to a hydrocarbon group containing at least one aromatic ring. A heteroaromatic group refers to an aromatic hydrocarbon group 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. A fused-ring aromatic group means that the ring of an aromatic group can have two or more rings, in which two carbon atoms are shared by two adjacent rings, that is, a fused ring. The fused heterocyclic aromatic group refers to a fused ring aromatic hydrocarbon group containing at least one heteroatom. For the purpose 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 purpose of the present invention , Is also considered to be an aromatic group or a heterocyclic aromatic group. For the purpose of the present invention, the fused-ring aromatic or fused heterocyclic aromatic ring system not only includes the system of aromatic groups or heteroaromatic groups, but also multiple aromatic groups or heterocyclic aromatic groups can be shortened Non-aromatic units are discontinuous (<10% of non-H atoms, and 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, diaryl ether, etc., are also considered to be fused-ring aromatic ring systems for the purpose of the present invention.

In a preferred embodiment, the aromatic group is selected from: benzene, naphthalene, anthracene, fluoranthene, phenanthrene, triphenylene, perylene, naphthacene, pyrene, benzopyrene, acenaphthene, Fluorene, and its derivatives; heteroaromatic groups selected from triazine, pyridine, pyrimidine, imidazole, furan, thiophene, benzofuran, benzothiophene, indole, carbazole, pyrroloimidazole, pyrrolopyrrole, thieno Pyrrole, thienothiophene, furopyrrole, furofuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole, quinoline, isoquinoline, o-naphthalene, quinoxaline, phenanthrene Pyridines, primidines, quinazolines, quinazolinones, and their derivatives.

In the present invention, the single bond connecting the substituent runs through the corresponding ring, which means that the substituent can be connected to an optional position of the ring, for example

Where R is connected to any substitutable position of the benzene ring.

In the present invention, the "light extraction layer" is located on the surface of the electrode of the organic electroluminescent device and away from the organic functional layer, preferably on the surface of the cathode.

An organic electroluminescence device comprising 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, It is characterized in that: the material of the light extraction layer contains a compound having a structure as shown in the general formula (1):

in:

Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from single bonds, substituted or unsubstituted aromatic groups with 5 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms Group, or substituted or unsubstituted non-aromatic ring system group with 3 to 30 ring atoms;

Ar _{1 is} selected from electron withdrawing groups;

Ar _{2 is} selected from any group in (A-1)-(A-4):

Each time X appears, it is independently selected from CR ₁ or N;

Each time R ₁ appears, it is independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and those having 1 to 20 C atoms. Linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 C atoms Branched or cyclic thioalkoxy groups, silyl groups, ketone groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aromatic groups having 7 to 20 C atoms Oxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, and those with 5 to 60 ring atoms An aryloxy group, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

In one embodiment, X are all independently selected from CR ₁ ;

In one embodiment, Ar _{2 is} selected from (A-1) or (A-4); preferably, Ar _{2 is} selected from (A-1).

In an embodiment, (A-1)-(A-4) is selected from one of the following groups:

Further, the general formula (1) is selected from one of the general formulas (2-1)-(2-3):

Further, the general formula (1) is selected from one of the following general formulas:

In one embodiment, Ar _{1 is} selected from electron withdrawing groups; the reason is that the electron withdrawing group can increase the electronic push and pull of the entire molecule, regulate the energy level and dipole moment of the molecule, and increase the ultraviolet absorption of the molecule below 400nm and 400nm. -800nm refractive index.

In an embodiment, the electron withdrawing group is selected from any group of (B-1)-(B-8):

in:

Each time X ₁ appears, it is independently selected from CR ₂ or N, and at least one X _{1 is} selected from N;

Each time Y appears, it is independently selected from NR ₃ , CR ₃ R ₄ , O, S, SiR ₃ R ₄ , S=O, SO ₂ or P(R ₃ );

Each occurrence of R ₂ -R ₄ is independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 The aryloxy group of ring atoms, the heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, adjacent R ₂ on the six-membered ring may further form a ring with each other.

Preferably, the electron withdrawing group is selected from (B-5) or (B-6); more preferably, the electron withdrawing group is selected from (B-5); more preferably, the electron withdrawing group is selected from:

Further, the electron withdrawing group is selected from:

Preferably, Y is selected from O, S or NR ₃ .

In a preferred embodiment, the electron withdrawing group is selected from one of the following groups:

The dotted line indicates the connection site.

In a preferred embodiment, the R _{3 is} selected from methyl, phenyl or naphthyl.

In a preferred embodiment, the electron withdrawing group is selected from the following groups:

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

More preferably, the electron withdrawing group is selected from one of the following groups, and the H atom on the ring may be further substituted:

In an embodiment, the general formula (1) is selected from the general formula (3-1):

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

Further, the general formula (3-1) is selected from the following general formulas:

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

In an embodiment, the general formula X is selected from C at the same time; more preferably, X ₁ is selected from CR ₂ ; more preferably, Y is selected from O, S or NR ₃ .

In an embodiment, the general formula X is selected from N at the same time; more preferably, X ₁ is selected from CR ₂ ; more preferably, Y is selected from O, S or NR ₃ .

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

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

In one embodiment, L ₁ , L ₂ and L ₃ as described above are independently selected from single bonds or the following groups:

in:

Each time X ₂ appears, it is independently selected from CR ₅ or N;

Each time Y ₁ appears, it is independently selected from NR ₅ , CR ₅ R ₆ , O, S, SiR ₅ R ₆ , S=O, SO ₂ or P(R ₅ );

Each time R ₅ and R ₆ appear, they are independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 A ring atom aryloxy group, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

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

In an 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

In an 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

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

More preferably, at least one is selected from single bonds and at least one is selected from

More preferably, one is selected from single bonds, and two are selected from

More preferably, two are selected from single bonds and one is selected from

In an embodiment, L ₁ , L ₂ and L _{3 are} independently selected from the following groups or combinations thereof:

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

Specifically, L ₁ , L ₂ and L _{3 are} independently selected from a single bond or one of the following groups:

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

Further, the general formula (1) is selected from the general formula (4-1):

Wherein: n1, n2, n3 are independently selected from any integer of 0-2 each time they appear. In one embodiment, at least one of n1, n2, and n3 is selected from 1 or 2. In one embodiment, at least two of n1, n2, and n3 are selected from 1 or 2. In one embodiment, n1, n2 , N3 are all selected from 1 or 2.

In one embodiment, n1 and n3 are selected from 1 or 2.

In one embodiment, X in the general formula (4-1) is independently selected from CR ₁ .

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

Furthermore, the general formula (4-1) is selected from the following general formulas:

Specifically, the material of the light extraction layer of the present invention includes a compound having the following structure, but is not limited to this:

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

According to the organic electroluminescent device of the present invention, the material of the light extraction layer requires a higher glass transition temperature, which improves the thermal stability of the material of the light extraction layer. In some preferred embodiments, the glass transition temperature T _g of the material of the light extraction layer is ≥100°C. In a preferred embodiment, T _g ≥120°C, and in a more preferred embodiment, T _g ≥ 140°C, in a more preferred embodiment, T _g ≥ 160°C, and in a most preferred embodiment, T _g ≥ 180°C.

In some embodiments, according to the organic electroluminescent device of the present invention, the refractive index of the material of the light extraction layer 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 material of the light extraction layer 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 2.85eV.

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

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

In one embodiment, according to the organic electroluminescent device of the present invention, the light extraction layer is located on the surface of the cathode.

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 the group consisting of electron injection layers, electron transport layers, and hole injection layers. One or more layers of the hole transport layer and the light-emitting layer, including at least one light-emitting layer.

In some preferred embodiments, the organic electroluminescent device according to the present invention, wherein the luminescent material in the luminescent layer is selected from singlet luminophores, triplet luminophores or TADF materials.

In some more preferred 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.

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

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

1. Singlet luminous body

Singlet emitters often have longer conjugated π-electron systems. So far, 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 disclosed in US7233019 and KR2006-0006760 The triarylamine derivative of pyrene.

In a preferred embodiment, the singlet luminophore can be selected from monostyrylamine, distyrylamine, ternary styrylamine, quaternary styrylamine, styrene phosphine, styrene ether and aromatic amine.

A monostyrylamine refers to a compound that contains an unsubstituted or substituted styryl group and at least one amine, preferably an aromatic amine. A dibasic styrylamine refers to a compound that contains two unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A ternary styrylamine refers to a compound that contains three unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A quaternary styrylamine refers to a compound that contains four unsubstituted or substituted styryl groups and at least one amine, preferably an aromatic amine. A preferred styrene is stilbene, which may be further substituted. The corresponding definitions of phosphines and ethers are similar to those of amines. An arylamine or aromatic amine refers to a compound containing three unsubstituted or substituted aromatic rings or heterocyclic ring systems directly linked to nitrogen. At least one of these aromatic or heterocyclic ring systems is preferred to the fused ring system, and preferably has at least 14 aromatic ring atoms. Among the preferred examples are aromatic anthracene amine, aromatic anthracene diamine, aromatic pyrene amine, aromatic pyrene diamine, aromatic pyrene diamine, and aromatic pyrene diamine. An aromatic anthracene amine refers to a compound in which a dibasic aryl amine group is directly linked to the anthracene, preferably at the 9 position. An aromatic anthracene diamine refers to a compound in which two divalent aryl amine groups are directly linked to the anthracene, preferably at positions 9,10. Aromatic pyrene amine, aromatic pyrene diamine, aromatic pyrene diamine and aromatic pyrene diamine have similar definitions, and the divalent aryl amine group is preferably linked to the 1, or 1, 6 position of pyrene.

Examples of singlet emitters based on vinylamine and aromatic amine are also preferred examples, and 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 patent documents listed above are hereby combined Included in this article as a reference.

An example of a singlet light emitter based on stilbene and its derivatives is US 5121029.

Further preferred singlet luminophores can be selected from indenofluorene-amine and indenofluorene-diamine, as disclosed in WO 2006/122630, benzindenofluorene-amine and benzindenofluorene-diamine , As disclosed in WO2008/006449, dibenzoindenofluorene-amine and dibenzoindenofluorene-diamine, as disclosed in WO2007/140847.

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; others Triarylamine derivatives of pyrene with specific structures are disclosed in CN105085334A and CN105037173A. Other materials that can be used as singlet light emitters are polycyclic aromatic hydrocarbon compounds, especially derivatives of the following compounds: anthracene such as 9,10-bis(2-naphthanthracene), 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, decacycloene, hexabenzocene, fluorene, spirobifluorene, arylpyrene (such as US20060222886), arylene ethylene (such as US5121029, US5130603), cyclopentadiene Alkenes such as tetraphenylcyclopentadiene, rubrene, coumarin, rhodamine, quinacridone, pyrans such as 4(dicyanomethylene)-6-(4-p-dimethylaminobenzene) Vinyl-2-methyl)-4H-pyran (DCM), thiopyran, bis(azinyl) imine boron compound (US 2007/0092753 A1), bis(azinyl) methylene compound, carbostyryl Compounds, oxazinones, benzoxazoles, benzothiazoles, benzimidazoles and pyrrolopyrrole dione. Some singlet light emitter materials can be found in the following patent documents: US 20070252517 A1, US 4769292, US 6020078, US 2007/0252517 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 luminous body

Triplet emitters are also called phosphorescent emitters. In a preferred embodiment, the triplet emitter 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 , It is connected to the metal atom M through one or more position bonding or coordination, n is an integer between 1 and 6. Preferably, the triplet luminophore contains a chelating ligand, that is, a ligand, which is coordinated to the metal through at least two binding points. It is particularly preferred 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 a preferred embodiment, the metal complexes that can be used as triplet emitters have the following forms:

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

Ar ⁴ , Ar ⁵ can be the same or different each time they appear. They are a cyclic group, where Ar ⁴ contains at least one donor atom, that is, an atom with a lone pair of electrons, such as nitrogen, through which the cyclic group interacts with Metal coordination connection; where 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, each of which can carry one or more substituent groups, they It can also be linked together by substituent groups; L'can be the same or different each time it appears, and is a bidentate chelating auxiliary ligand, preferably a monoanionic bidentate chelating ligand; q1 can be 0 , 1, 2 or 3, preferably 2 or 3; q2 can be 0, 1, 2 or 3, preferably 1 or 0. Examples of organic ligands can 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 preferably be selected from acetone acetate or picric acid.

Some examples of the materials and applications of triplet emitters can be found in the following patent documents and documents: WO200070655, WO200141512, WO200202714, WO200215645, WO2005033244, WO2005019373, US20050258742, US20070087219, US20070252517, US2008027220, WO2009146770, US20090061681, WO20090061681, WO20090061681, WO20090061681, WO20090151180 , WO2010054731, WO2011157339, WO2012007087, WO201200708, WO2013107487, WO2013094620, WO2013174471, WO2014031977, WO2014112450, WO2014007565, WO2014024131, 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. J. Am. Chem. Soc. (1974), 998, Ma et al. Synth. Metals (1998), 245. 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 material (TADF)

Traditional organic fluorescent materials can only emit light with 25% singlet excitons formed by electrical excitation, 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 of the heavy atom center, it can effectively use the singlet excitons and triplet excitons formed by electric excitation to emit light, so that the internal quantum efficiency of the device reaches 100%. However, phosphorescent materials are expensive, poor material stability, serious device efficiency roll-off and other issues limit their application in OLEDs. Thermally activated delayed fluorescent light-emitting materials are the third generation of organic light-emitting materials developed after organic fluorescent materials and organic phosphorescent materials. Such materials generally have a small singlet-triplet energy level difference (ΔE _st ), and the triplet excitons can be converted into singlet excitons to emit light through the inter-system crossing. This can make full use of the singlet and triplet excitons formed under electrical excitation. The quantum efficiency in 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 OLED field is broad.

The TADF material needs to have a small singlet-triplet energy level difference, preferably ΔEst<0.3eV, next best ΔEst<0.2eV, and most preferably ΔEst<0.1eV. In a preferred embodiment, the TADF material has a relatively small ΔEst, and in another preferred embodiment, TADF has a better fluorescence quantum efficiency. Some TADF light-emitting 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, 11311, 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 patents or articles listed above are hereby incorporated by reference.

Some examples of suitable TADF luminescent materials are listed below:

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

The anode may include a conductive metal or metal oxide, or a conductive polymer. The anode can easily inject holes into a hole injection layer (HIL) or a hole transport layer (HTL) or a light emitting layer. In one embodiment, the absolute value of the difference between the work function of the anode and the luminous body in the light-emitting layer or the HOMO energy level or the valence band energy level of the p-type semiconductor material as HIL or HTL or electron blocking layer (EBL) is less than 0.5 eV, preferably less than 0.3 eV, most preferably less than 0.2 eV. Examples of anode materials include but are not limited to: Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum doped zinc oxide (AZO), and the like. Other suitable anode materials are known, and those of ordinary skill in the art can easily select and use them. 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), and the like. In some embodiments, the anode is patterned and structured. Patterned ITO conductive substrates are commercially available and can be used to prepare devices according to the present invention.

The cathode may include 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 work function of the cathode and the LUMO energy level or conductivity of the luminous body in the light-emitting layer or the n-type semiconductor material as the electron injection layer (EIL) or electron transport layer (ETL) or hole blocking layer (HBL) The absolute value of the difference in band level 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 the cathode of an OLED can be used as the cathode material 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), and the like.

The light extraction layer material needs to have a suitable energy level structure, which has strong absorption in the region with a wavelength less than 400nm, and visible light with a wavelength greater than 400nm absorbs weakly or close to zero, so as to prevent the internal materials of the device from being damaged by high-energy light in the subsequent process. . At the same time, the light extraction layer material has a relatively 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 reflectance 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 material constituting the light extraction layer is preferably larger than the refractive index of the adjacent electrode.

In one embodiment, in the organic electroluminescent device according to the present invention, especially the organic light emitting diode, the light extraction layer is located on the surface of the cathode.

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 10nm to 200nm, preferably 20nm to 150nm, more preferably 30nm to 100nm, most preferably 40nm To 90nm.

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 an aromatic amine compound containing a condensed ring, which is selected from the structure shown in general formula (5):

in:

Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from single bonds, substituted or unsubstituted aromatic groups with 5 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms Group, or substituted or unsubstituted non-aromatic ring system group with 3 to 30 ring atoms;

Each time X appears, it is independently selected from CR ₁ or N;

Each time X ₁ appears, it is independently selected from CR ₂ or N, and at least one X _{1 is} selected from N, adjacent R ₂ on the six-membered ring may form a ring with each other;

Each time Y appears, it is independently selected from NR ₃ , CR ₃ R ₄ , O, S, SiR ₃ R ₄ , S=O, SO ₂ or P(R ₃ ); preferably, Y is selected from O, S, NR ₃ .

Each time R ₁ -R ₄ appears, they are independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 A ring atom aryloxy group, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

In one embodiment,

Selected from

further,

Selected from

m is selected from any integer from 0-4.

In one embodiment,

Selected from any of the following groups:

Further, the general formula (5) is selected from any of the following general formulas:

Further, general formula (5) is selected from any structure of general formulas (6-1)-(6-6):

In one embodiment, X in the above general formula is selected from CR ₁ ; in one embodiment, X ₁ in the above general formula is selected from CR ₂ ; further, R _{1 is} selected from H, and R _{2 is} selected from phenyl.

In one embodiment, the organic compound according to the present invention, wherein L ₁ , L ₂ and L _{3 are} independently selected from a single bond or one of the following groups:

in:

Each time X ₂ appears, it is independently selected from CR ₅ or N;

Each time Y ₁ appears, it is independently selected from NR ₅ , CR ₅ R ₆ , O, S, SiR ₅ R ₆ , S=O, SO ₂ or P(R ₅ );

Each time R ₅ and R ₆ appear, they are independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 A ring atom aryloxy group, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.

In one embodiment, L ₁ and L ₂ and L _{3 are} independently selected from the following groups:

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

Specifically, L ₁ , L ₂ and L _{3 are} independently selected from a single bond or one of the following groups:

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

In an embodiment, _{at least one of L 1} , L ₂ and L _{3 is} selected from a single bond; in an embodiment, _{at least two of L 1} , L ₂ and L ₃ are selected from a single bond; in an embodiment, L ₁ , L ₂ and L ₃ are all selected from single bonds. 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 an embodiment, _{at least one of L 1} , L ₂ and L _{3 is} selected from benzene or naphthalene; in an embodiment, _{at least two of L 1} , L ₂ and L ₃ are selected from benzene or naphthalene; in an 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, L ₁ , L ₂ and L _{3 are} at least two benzenes; 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 single bonds or benzene; more preferably, at least one is selected from single bonds and at least one is selected from benzene; more preferably, one is selected from single bonds, two One is selected from benzene.

In one embodiment, the organic compound according to the present invention is selected from the structure shown in general formula (7):

Wherein: n1, n2, n3 are independently selected from any integer of 0-2 each time they appear. The priority scheme is as described above.

X, X ₁ , X ₂ , and Y have the meanings described above.

Specifically, the fused ring-containing aromatic amine compound according to the present invention is selected from any one of the above-mentioned structural formulas (G-106)-(G-207) and (G-210)-(G-212) Kind, but not limited to this.

The aromatic amine compound containing fused ring according to 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 material for a light extraction layer includes the aromatic amine compound containing a condensed ring as described above.

An object of the present invention is to provide a material solution for vapor-deposited OLED.

In some embodiments, the fused ring-containing aromatic amine compound according to the present invention has a molecular weight ≤1200g/mol, preferably ≤1100g/mol, very preferably ≤1000g/mol, more preferably ≤950g/mol, most preferably ≤ 900g/mol.

The present invention also relates to a composition comprising at least one fused ring-containing aromatic amine compound represented by the above general formula (4), and at least one organic solvent; the at least one organic solvent is selected from aromatic Aliphatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefin compound, or borate or phosphate compound, or two or more solvents mixture.

The present invention further relates to an organic electronic device comprising at least one aromatic amine compound containing a condensed ring as described above. The organic electronic device according to the present invention can be selected from, but not limited to, organic light-emitting diodes (OLED), organic photovoltaic cells, organic light-emitting batteries, organic field effect tubes, organic light-emitting field effect tubes, organic lasers, organic spintronics Devices, organic sensors, organic plasmon emitting diodes, etc., are particularly preferably OLEDs.

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 appended claims summarize the scope of the present invention. Under the guidance of the concept of the present invention, those skilled in the art should It is realized 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 embodiment

The synthesis method of the compound according to the present invention is exemplified, but the present invention is not limited to the following examples.

Synthesis of compound G-17:

Compound 1-1 (5.38g, 20mmol) was dissolved in anhydrous toluene, 1-2 (5.64g, 20mmol), sodium tert-butoxide (2.11g, 22mmol) and tridibenzylidene acetone dipalladium (0.9 g, 1 mmol), after replacing the nitrogen for three times, add tri-tert-butyl phosphine (1 mmol), gradually increase the temperature to 80° C., and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 6.4 g of compound 1-3 with a yield of 68%.

Dissolve compound 1-3 (5.65g, 12mmol) in anhydrous toluene, add 1-4 (2.81g, 12mmol), sodium tert-butoxide (1.25g, 13mmol) and dipalladium tridibenzylideneacetone (0.55 g, 0.6 mmol), after replacing nitrogen for three times, add tri-tert-butyl phosphine (0.6 mmol), gradually increase the temperature to 80° C., and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 3.9 g of compound G-17, MS: [M] ⁺ =625, yield 52%.

Synthesis of compound G-208:

Compound 1-1 (5.38g, 20mmol), 2-2 (7.88g, 20mmol) were dissolved in 100mL of anhydrous toluene, sodium tert-butoxide (2.11g, 22mmol) and tridibenzylidene acetone dipalladium ( 0.9g, 1mmol), after replacing nitrogen for three times, add tri-tert-butylphosphine (1mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 8.4 g of compound 2-3 with a yield of 72%.

Compounds 2-3 (7g, 12mmol), 2-4 (2.48g, 12mmol) were dissolved in 100mL of anhydrous toluene, sodium tert-butoxide (1.25g, 13mmol) and three dibenzylidene acetone dipalladium (0.55 g, 0.6 mmol), after replacing nitrogen for three times, add tri-tert-butyl phosphine (0.6 mmol), gradually increase the temperature to 80° C., and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 5.54 g of product G-208, MS: [M] ⁺ =710, yield 65%.

Synthesis of compound G-109:

Compound 3-1 (2.6g, 10mmol), 9-bromophenanthrene (5.63g, 22mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (2.02g, 21mmol) and tridibenzylidene acetone dipalladium (460mg , 0.5mmol), after replacing the nitrogen for three times, add tri-tert-butylphosphine (0.5mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 3.18 g of product G-109, MS: [M] ⁺ =612, yield 52%.

Synthesis of compound G-163:

Compound 4-1 (3.15g, 15mmol), 2-bromophenanthrene (8.19g, 32mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (3.07g, 32mmol) and three dibenzylidene acetone dipalladium (0.73 g, 0.8 mmol), after replacing the nitrogen for three times, add tri-tert-butyl phosphine (0.8 mmol), gradually increase the temperature to 80° C., and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 6.9 g of product G-163, MS: [M] ⁺ =562, yield 82%.

Synthesis of compound G-209:

Anthracenecarboxylic acid (3g, 10mmol) and o-hydroxyaniline (1.2g, 11mmol) were added to the polyphosphoric acid, the temperature was gradually raised to 140°C, and the reaction was stirred. After the TLC dot plate reactant disappears, remove the heat source. After the system is cooled, keep an ice-water bath, add NaOH aqueous solution, and filter under reduced pressure to obtain 3.2 g of Intermediate 5-1 with a yield of 86%.

Compound 1-1 (5.38g, 20mmol), 2-bromonaphthalene (4.12g, 20mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (2.02g, 21mmol) and tridibenzylidene acetone dipalladium ( 0.9g, 1mmol), after replacing nitrogen for three times, add tri-tert-butylphosphine (1mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 5.93 g of Intermediate 5-3 with a yield of 75%.

Compound 5-3 (3.16g, 8mmol), 5-1 (2.98g, 8mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (0.86g, 9mmol), and tridibenzylidene acetone dipalladium ( 0.37g, 0.4mmol), after replacing nitrogen for three times, add tri-tert-butylphosphine (0.4mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC spot plate reactants disappear, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 4.5 g of product G-209, MS: [M] ⁺ =688, with a total yield of 82%.

Synthesis of compound G-210:

Compound 1-1 (5.38g, 20mmol), 9-bromophenanthrene (5.12g, 20mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (2.01g, 21mmol) and tridibenzylidene acetone dipalladium ( 0.9g, 1mmol), after replacing nitrogen for three times, add tri-tert-butylphosphine (1mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 5.34 g of Intermediate 6-2 with a yield of 60%.

Compound 6-2 (4.45g, 10mmol), 6-3 (2.86g, 10mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.06g, 11mmol) and tridibenzylidene acetone dipalladium (0.46 g, 0.5 mmol), after replacing the nitrogen for three times, add tri-tert-butyl phosphine (0.5 mmol), gradually increase the temperature to 80° C., and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 5 g of product G-210, MS: [M] ⁺ =651, with a yield of 77%.

Synthesis of compound G-211:

Compound 7-1 (3.39g, 15mmol), 2-bromophenanthrene (3.84g, 15mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.73g, 18mmol) and tridibenzylidene acetone dipalladium ( 0.73g, 0.8mmol), after replacing the nitrogen for three times, add tri-tert-butylphosphine (0.8mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 5.18 g of product with a yield of 86%.

Compound 7-2 (4.02g, 10mmol) and 7-3 (3.34g, 10mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (1.06g, 11mmol) and tridibenzylidene acetone dipalladium (0.46 g, 0.5 mmol), after replacing the nitrogen for three times, add tri-tert-butyl phosphine (0.5 mmol), gradually increase the temperature to 80° C., and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 4.07 g of product G-211, MS: [M] ⁺ =656, yield 62%.

Synthesis of compound G-201:

Compound 7-1 (3.39g, 15mmol) and 7-3 (10.7g, 32mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (3.07g, 32mmol), and tridibenzylidene acetone dipalladium ( 0.73g, 0.8mmol), after replacing the nitrogen for three times, add tri-tert-butylphosphine (0.8mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 5.8 g of product G-201, MS: [M] ⁺ =734, yield 53%.

Synthesis of compound G-158:

The compound dibromoaniline (9.75g, 30mmol), 9-phenanthrene boronic acid (13.76g, 62mmol) were dissolved in anhydrous toluene and methanol, potassium carbonate (12.4g, 90mmol) and tetrakistriphenylphosphine palladium (1.58g) , 1.5mmol), after replacing nitrogen for three times, the temperature was gradually raised to 80°C, and the reaction was stirred. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through silica gel to obtain 13.6 g of product with a yield of 87%.

Compound 9-1 (4.17g, 8mmol), 9-2 (2.31g, 8mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (0.86g, 9mmol) and tridibenzylidene acetone dipalladium (0.37 g, 0.4mmol), after replacing nitrogen for three times, add tri-tert-butylphosphine (0.4mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC spot plate reactants disappear, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 5.26 g of product G-158, MS: [M] ⁺ =730, yield 90%.

Synthesis of compound G-155:

Compound 9-1 (4.17g, 8mmol), 10-2 (2.18g, 8mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (0.86g, 9mmol) and tridibenzylidene acetone dipalladium (0.37 g, 0.4mmol), after replacing the nitrogen for three times, add tri-tert-butylphosphine (0.4mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC dot plate reactant disappears, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 4.91 g of product G-155, MS: [M] ⁺ =714, yield 86%.

Synthesis of compound G-212:

Compound 9-1 (4.17g, 8mmol) and 11-2 (2.58g, 8mmol) were dissolved in anhydrous toluene, sodium tert-butoxide (0.86g, 9mmol) and tridibenzylidene acetone dipalladium (0.37 g, 0.4mmol), after replacing nitrogen for three times, add tri-tert-butylphosphine (0.4mmol), gradually increase the temperature to 80°C, and stir the reaction. After the TLC spot plate reactants disappear, remove the heat source. After the system was cooled, water was added, the organic layer was separated, and extracted three times with ethyl acetate, concentrated under reduced pressure, and passed through a silica gel column to obtain 4.95 g of product G-212, MS: [M] ⁺ =764, yield 81%.

Extinction coefficient and refractive index calculation

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

The results are shown in Table 1:

Table 1

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

Preparation and characterization of OLED devices

The following specific examples illustrate the preparation process of the above-mentioned OLED device in detail. As shown in Figure 1, 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 ITO conductive glass anode layer was cleaned, followed by ultrasonic cleaning with deionized water, acetone, and isopropanol for 15 minutes, and then treated in a plasma cleaner for 5 minutes to improve the work function of the electrode. On the ITO anode layer, the hole injection layer material HATCN is evaporated by vacuum evaporation method, the thickness is 5nm, and the evaporation rate is

On the hole injection layer, the hole transport material SNFFB is vapor-deposited by a vacuum vapor deposition method to a thickness of 80 nm. A light-emitting layer is vapor-deposited on the hole transport layer, m-CP is used as the host material, Ir(p-ppy) _{3 is} used as the doping material, _{and the mass ratio of Ir(p-ppy) 3} and m-CP is 1:9 , The thickness is 30nm. On the light-emitting layer, the electron transport material NaTzF _{2 was} vapor-deposited by a vacuum vapor deposition method to a thickness of 30 nm. On the electron transport layer, the electron injection layer LiF is vacuum-evaporated to a thickness of 1 nm. This layer is the electron injection layer 7. On the electron injection layer, the cathode Mg:Ag layer is vacuum-evaporated, the Mg:Ag doping ratio is 9:1, and the thickness is 15nm. On the cathode layer, the light extraction layer compound G-17 was vapor-deposited by a vacuum vapor deposition method to a thickness of 60 nm.

Device Example 1: The light extraction layer compound of the organic electroluminescence device was changed to G-17.

Device Example 2: The light extraction layer compound of the organic electroluminescence device was changed to G-208.

Device Example 3: The light extraction layer compound of the organic electroluminescence device was changed to G-109.

Device Example 4: The light extraction layer compound of the organic electroluminescence device was changed to G-163.

Device Example 5: The light extraction layer compound of the organic electroluminescence device was changed to G-209.

Device Example 6: The light extraction layer compound of the organic electroluminescence device was changed to G-210.

Device Example 7: The light extraction layer compound of the organic electroluminescence device was changed to G-211.

Device Example 8: The light extraction layer compound of the organic electroluminescence device was changed to G-201.

Device Example 9: The light extraction layer compound of the organic electroluminescence device was changed to G-158.

Device Example 10: The light extraction layer compound of the organic electroluminescence device was changed to G-155.

Device Example 11: The light extraction layer compound of the organic electroluminescence device was changed to G-212.

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

The structure of the compound involved in the device is as follows:

Table 2

serial number	Light extraction layer compound	Luminous efficiency
Device Example 1	G-17	1.05
Device Example 2	G-208	1.07
Device Example 3	G-109	1.15
Device Example 4	G-163	1.24
Device Example 5	G-209	1.1
Device Example 6	G-210	1.12
Device Example 7	G-211	1.16
Device Example 8	G-201	1.12
Device Example 9	G-158	1.11
Device Example 10	G-155	1.21
Device Example 11	G-212	1.15
Comparative example 1	CBP	1

The luminous efficiency in Table 2 is the 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 compound of the present invention can effectively improve the luminous efficiency of the organic electroluminescent device as the light extraction layer material.

The technical features of the above-mentioned embodiments can be combined arbitrarily. In order to make the description concise, all possible combinations of the various technical features in the above-mentioned embodiments are not described. However, as long as there is no contradiction in the combination of these technical features, All should be considered as the scope of this specification.

The above-mentioned embodiments only express several implementation modes of the present invention, and their description is relatively specific and detailed, but they should not be understood as a limitation on the scope of the invention patent. It should be pointed out that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can be made, and these all fall within the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention should be subject to the appended claims.

Claims (18)

1. An organic electroluminescence device comprising 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, It is characterized in that: the material of the light extraction layer contains a compound having a structure as shown in the general formula (1):

   

   in:

   Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from single bonds, substituted or unsubstituted aromatic groups with 5 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms Group, or substituted or unsubstituted non-aromatic ring system group with 3 to 30 ring atoms;

   Ar _{1 is} selected from electron withdrawing groups;

   Ar _{2 is} selected from any group in (A-1)-(A-4):

   

   Each time X appears, it is independently selected from CR ₁ or N;

   Each time R ₁ appears, it is independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and those having 1 to 20 C atoms. Linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 C atoms Branched or cyclic thioalkoxy groups, silyl groups, ketone groups having 1 to 20 C atoms, alkoxycarbonyl groups having 2 to 20 C atoms, aromatic groups having 7 to 20 C atoms Oxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl, Br, F. Crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, and those with 5 to 60 ring atoms An aryloxy group, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
2. The organic electroluminescence device according to claim 1, wherein the (A-1)-(A-4) is selected from one of the following groups:

   
3. The organic electroluminescence device according to claim 2, wherein the material of the light extraction layer comprises a compound having a structure shown in any one of the general formulas (2-1)-(2-3) :

   
4. The organic electroluminescence device according to claim 1, wherein the electron withdrawing group is selected from any group of (B-1)-(B-8):

   

   in:

   Each time X ₁ appears, it is independently selected from CR ₂ or N, and at least one X _{1 is} selected from N;

   Each time Y appears, it is independently selected from NR ₃ , CR ₃ R ₄ , O, S, SiR ₃ R ₄ , S=O, SO ₂ or P(R ₃ );

   Each occurrence of R ₂ -R ₄ is independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 The aryloxy group of ring atoms, the heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups, adjacent R ₂ on the six-membered ring may further form a ring with each other.
5. The organic electroluminescence device according to claim 4, wherein the electron withdrawing group is selected from (B-5) or (B-6).
6. The organic electroluminescence device according to claim 5, wherein the electron withdrawing group is selected from one of the following groups:

   
7. The organic electroluminescence device according to claim 5, wherein the material of the light extraction layer comprises a compound having a structure represented by the general formula (3-1):

   
8. 8. The organic electroluminescent device of claim 7, wherein:

   

   Selected from

   
9. The organic electroluminescent device according to claims 1-6, wherein said L ₁ , L ₂ and L _{3 are} independently selected from single bonds or one of the following groups:

   

   in:

   Each time X ₂ appears, it is independently selected from CR ₅ or N;

   Each time Y ₁ appears, it is independently selected from NR ₅ , CR ₅ R ₆ , O, S, SiR ₅ R ₆ , S=O, SO ₂ or P(R ₅ );

   Each time R ₅ and R ₆ appear, they are independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 A ring atom aryloxy group, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
10. The organic electroluminescence device according to claim 9, characterized in that: the material of the light extraction layer comprises a compound having a structure represented by the general formula (4-1):

    

    Wherein: n1, n2, n3 are independently selected from any integer of 0-2 each time they appear.
11. The organic electroluminescent device according to any one of claims 1-6, wherein the organic electroluminescent device is an organic light-emitting diode, wherein the light extraction layer is located on the cathode surface of the organic light-emitting diode superior.
12. A fused ring-containing aromatic amine compound, which is characterized in that it has a structure as shown in the general formula (5):

    

    in:

    Each time L ₁ , L ₂ and L ₃ appear, they are independently selected from single bonds, substituted or unsubstituted aromatic groups with 5 to 30 ring atoms, and substituted or unsubstituted heteroaromatic groups with 5 to 30 ring atoms Group, or substituted or unsubstituted non-aromatic ring system group with 3 to 30 ring atoms;

    Each time X appears, it is independently selected from CR ₁ or N;

    Each time X ₁ appears, it is independently selected from CR ₂ or N, and at least one X _{1 is} selected from N;

    Each time Y appears, it is independently selected from NR ₃ , CR ₃ R ₄ , O, S, SiR ₃ R ₄ , S=O, SO ₂ or P(R ₃ );

    Each occurrence of R ₁ -R ₄ is independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 A ring atom aryloxy group, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
13. The aromatic amine compound containing fused ring according to claim 12, wherein:

    

    Selected from

    
14. The fused ring-containing aromatic amine compound according to claim 12, wherein the general formula (5) is selected from one of the general formulas (6-1)-(6-6):

    
15. The fused ring-containing aromatic amine compound according to any one of claims 12-14, wherein said L ₁ , L ₂ and L _{3 are} independently selected from single bonds or one of the following groups:

    

    in:

    Each time X ₂ appears, it is independently selected from CR ₅ or N;

    Each time Y ₁ appears, it is independently selected from NR ₅ , CR ₅ R ₆ , O, S, SiR ₅ R ₆ , S=O, SO ₂ or P(R ₅ );

    Each time R ₅ and R ₆ appear, they are independently selected from hydrogen, D, linear alkyl groups having 1 to 20 C atoms, linear alkoxy groups having 1 to 20 C atoms, and 1 to 20 C atoms. C-atom linear thioalkoxy, branched or cyclic alkyl having 3 to 20 C atoms, branched or cyclic alkoxy having 3 to 20 C atoms, having 3 to 20 A branched or cyclic thioalkoxy group having a C atom, a silyl group, a keto group having 1 to 20 C atoms, an alkoxycarbonyl group having 2 to 20 C atoms, having 7 to 20 C atoms Atoms of aryloxycarbonyl, cyano, carbamoyl, haloformyl, formyl, isocyano, isocyanate, thiocyanate, isothiocyanate, hydroxyl, nitro, CF ₃ , Cl , Br, F, crosslinkable groups, substituted or unsubstituted aromatic groups with 5 to 60 ring atoms, substituted or unsubstituted heteroaromatic groups with 5 to 60 ring atoms, 5 to 60 A ring atom aryloxy group, a heteroaryloxy group having 5 to 60 ring atoms, or a combination of these groups.
16. The aromatic amine compound containing a condensed ring according to claim 15, wherein the aromatic amine compound containing a condensed ring has a structure as shown in the general formula (7):

    

    Wherein: n1, n2, n3 are independently selected from any integer of 0-2 each time they appear.
17. A composition, characterized in that it comprises at least one aromatic amine compound containing a condensed ring according to any one of claims 12-16, and at least one organic solvent.
18. A light extraction layer material, characterized in that it contains the fused ring-containing aromatic amine compound according to any one of claims 12-16.

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