A composite material, its preparation method and application

Abstract

The present invention provides a composite material, a preparation method and an application thereof. The composite material comprises a first layer and a second layer which are stacked in sequence; the composition of the first layer comprises H1, and the composition of the second layer comprises N1; the structures of H1 and N1 are shown in Formula I. The organic electroluminescent device prepared from the composite material provided by the present invention has high current efficiency, long lifespan and high brightness.

Description

Technical Field

[0001] The present invention belongs to the field of materials, and particularly relates to a composite material, a preparation method and an application thereof, and more particularly to a composite material with high efficiency, a preparation method and an application thereof. Background Art

[0002] Recently, with the increase in the size of displays, people have become increasingly interested in flat display elements that occupy less space. In this field, the technology of organic light-emitting displays including organic light-emitting diodes (OLEDs) as flat display elements has developed rapidly. Organic light-emitting diodes emit light by annihilating pairs of holes and electrons generated by injecting holes and electrons from a hole injection electrode (anode) and an electron injection electrode (cathode) into an emission layer between the anode and the cathode. Such organic light-emitting diodes can be formed on a flexible transparent substrate such as plastic, can be operated at a low voltage, consume relatively low power, and have good color reproduction.

[0003] CN108780853A discloses a variety of host materials and an organic electroluminescent device comprising the variety of host materials. By including a variety of host compounds in a specific combination, the organic electroluminescent device can have improved lifetime properties. The structures of the host compounds are as follows:

[0004]

[0005] CN108290875A discloses a new compound capable of improving the luminous efficiency, stability and lifetime of an element, an organic electronic element using the compound, and an electronic device thereof. By using the compound, the high luminous efficiency, low driving voltage, high heat resistance of the element can be improved, and the color purity and lifetime can be improved. The structure of the compound is as follows:

[0006]

[0007] Due to the gradually increasing requirements for organic electroluminescent devices, the demand for materials for new organic electroluminescent devices is more urgent. Therefore, how to provide a material for organic electroluminescent devices with high efficiency and long lifetime has become an urgent problem to be solved. Summary of the Invention

[0008] Aiming at the deficiencies of the prior art, the purpose of the present invention is to provide a composite material, a preparation method and an application thereof, and more particularly to provide a composite material with high efficiency, a preparation method and an application thereof. The organic electroluminescent device prepared from the composite material provided by the present invention has high current efficiency, long lifetime and high brightness.

[0009] To achieve the object of the present invention, the following technical solutions are adopted:

[0010] In a first aspect, the present invention provides a composite material, which comprises a first layer and a second layer stacked in sequence.

[0011] The composition of the first layer comprises H1, and the composition of the second layer comprises N1. The first layer and the second layer are directly stacked or indirectly stacked through other materials.

[0012] The structures of H1 and N1 are shown in Formula I:

[0013]

[0014] wherein Y is selected from O, S or CR Y1 R Y2 .

[0015] The R Y1 , R Y2 are independently selected from substituted or unsubstituted C1-C30 alkyl or substituted or unsubstituted C6-C30 aryl.

[0016] The R Y1 , R Y2 exist independently or are connected to R 14 or / and R 13 to form ring A.

[0017] The R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C30 alkynyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1-C30 alkoxy or substituted or unsubstituted C6-C30 aryloxy, and R1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 at least one is selected from wherein in the substituted or unsubstituted C1-C30 alkyl, optionally one or at least two non-adjacent methylene groups are independently replaced by -O- or -S-; in the substituted or unsubstituted C2-C30 alkenyl, optionally one or at least two non-adjacent methylene groups are independently replaced by -O- or -S-.

[0018] Preferably, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 is independently selected from any one of hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, 4-tolyl, methoxy, ethoxy, propoxy, dimethylamino, methylethylamino, diethylamino, diphenylamino or phenylmethylamino.

[0019] Preferably, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16At least one of them is selected from any one of methyl, ethyl, isopropyl, tert-butyl, phenyl, 4-tolyl, methoxy, ethoxy, propoxy, dimethylamino, methylethylamino, diethylamino, diphenylamino or phenylmethylamino.

[0020] Said R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 Exist independently or two adjacent ones are connected to form ring B.

[0021] Said ring A and ring B are selected from substituted or unsubstituted benzene rings.

[0022] Said L 1 , L 2 , L 3 Independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene or a substituted or unsubstituted C2-C30 heteroarylene.

[0023] Said Ar 1 , Ar 2 Independently selected from a substituted or unsubstituted C6-C60 aryl or a substituted or unsubstituted C2-C60 heteroaryl.

[0024] Said X 1 Is selected from N or Cl X1 R X1 , X 2 Is selected from N or Cl X2 R X2 , X 3 Is selected from N or Cl X3 R X3 , X 4 Is selected from N or Cl X4 R X4 , X 5 Is selected from N or Cl X5 R X5 , X 6 Is selected from N or Cl X6 R X6 .

[0025] Said R X1 , R X2 , RX3 , R X4 , R X5 , R X6 are independently selected from any one of P1, hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C2-C60 heteroaryl, and the structure of the P1 is shown in Formula II:

[0026]

[0027] The L X1 , L X2 , L X3 , L X4 , L X5 , L X6 are independently selected from any one of a single bond, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C2-C30 heteroarylene.

[0028] The L X1 R X1 , L X2 R X2 , L X3 R X3 , L X4 R X4 , L X5 R X5 , L X6 R X6 exist independently or two adjacent ones are connected to form a ring C.

[0029] The ring C is selected from a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.

[0030] The R a1 , R a2 , R a3 , R a4 , R a5 , R a6 , R a7 , R a8Independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1-C30 alkoxy or substituted or unsubstituted C6-C30 aryloxy, wherein one or at least two non-adjacent methylene groups in the substituted or unsubstituted C1-C30 alkyl may be independently replaced by -O- or -S-.

[0031] Said R a1 , R a2 , R a3 , R a4 , R a5 , R a6 , R a7 , R a8 Exist independently or two adjacent ones are connected to form ring D.

[0032] Said ring D is selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C2-C30 heteroaryl.

[0033] Preferably, at least one of said R 3 , R 4 , R 5 , R 6 is selected from

[0034] Preferably, at least one of said R 4 or R 6 is selected from

[0035] Preferably, said L 1 , L 2 , L 3 Independently selected from any one of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted dibenzofuranylene or substituted or unsubstituted dibenzothiophenylene.

[0036] Preferably, said Ar 1 , Ar 2 Independently selected from the following substituted or unsubstituted groups:

[0037]

[0038] Any one of the above, and the substituent of the substitution is selected from any one of deuterium, halogen, cyano, C1-C12 alkyl, or C1-C12 alkoxy.

[0039] Preferably, the N1 is selected from any one of N2, N3, N4, or N5, and the structures of N2, N3, N4, and N5 are shown in Formula III:

[0040]

[0041] Preferably, in N2, R x2 , R x4 , R x6 have the same defined range as above, and among R x2 , R x4 , R x6 there is exactly one item that is P1.

[0042] Preferably, in N3, R x2 , R x3 , R x4 , R x6 have the same defined range as above, and among R x2 , R x3 , R x4 , R x6 there is exactly one item that is P1.

[0043] Preferably, in N4, R x2 , R x6 , R x7 , R x8 , R x9 , R x10 are independently selected from any one of P1, hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C2-C60 heteroaryl, and among R x2 , R x6 there is exactly one item that is P1.

[0044] Preferably, in N5, R x1 , R x6 , R x7 , R x8 , R x9 , R x10 are independently selected from any one of P1, hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C2-C60 heteroaryl, and among R x1 , Rx6 Only one of them is P1.

[0045] Preferably, the N1 is selected from any one of the following substituted or unsubstituted groups substituted by P1:

[0046]

[0047]

[0048]

[0049]

[0050] where represents the site connected to P1, and the substituent of the substitution is selected from any one of deuterium, halogen, cyano, C1-C12 alkyl or C1-C12 alkoxy.

[0051] Preferably, the L X1 、L X2 、L X3 、L X4 、L X5 、L X6 are independently selected from any one of a single bond, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl or a substituted or unsubstituted benzocarbazolyl.

[0052] Preferably, P1 is selected from any one of the products of the condensation of any two adjacent ones of P2, P3, P4, P5, P6, P7, P8 or P1 in R a1 -R a8 with P10, and the structures of P2, P3, P4, P5, P6, P7, P8, P10 are shown in Formula IV:

[0053]

[0054] wherein, R a1 、R a2 、R a5 、R a6 、R a7 、R a8 、R a9 、R a10 、R a11 、R a12 in P2, R a1 、R a4 、R a5 、Ra6 , R a7 , R a8 , R a9 , R a10 , R a11 , R a12 , the R in P4 a3 , R a4 , R a5 , R a6 , R a7 , R a8 , R a9 , R a10 , R a11 , R a12 , the R in P5 a1 , R a2 , R a7 , R a8 , R a9 , R a10 , R a11 , R a12 , the R in P6 a1 , R a4 , R a7 , R a8 , R a9 , R a10 , R a11 , R a12 , the R in P7 a3 , R a4 , R a7 , R a8 , R a9 , R a10 , R a11 , R a12 , the R in P8 a1 , R a4 , R a5 , R a8 , R a9 , R a10 , R a11 , R a12 , the R in P10 b1 , R b2 , R b3 , R b4Independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1-C30 alkoxy or substituted or unsubstituted C6-C30 aryloxy, and independently existing or adjacent two of them connecting to form ring D, the ring D has the same defined range as above, wherein optionally one or at least two non-adjacent methylene groups in the substituted or unsubstituted C1-C30 alkyl are independently replaced by -O- or -S-, and the * in P10 refers to the fusion site; the X b Selected from O, S, CR Xb1 R Xb2 Or NR Xb3 Any one of them, wherein R Xb1 、R Xb2 Independently selected from substituted or unsubstituted C1-C4 alkyl or substituted or unsubstituted C6-C30 aryl, preferably methyl or phenyl, the R Xb1 、R Xb2 Independently exist or connect to form ring E, and the ring E is a fluorene ring; the R Xb3 Selected from substituted or unsubstituted C6-C30 aryl or C2-C30 heteroaryl, preferably phenyl, biphenyl, terphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, pyridyl-substituted phenyl or phenyl-substituted pyridyl.

[0055] Preferably, the product of any adjacent two of R a1 -R a8 in P1 fused with P10 is selected from any one of P11, P12, P13 or P14, and the structures of P11, P12, P13, P14 are shown in formula V:

[0056]

[0057] Among them, the R b1 、R b2 、R b3 、R b4 、R b5 、R b6 、R b7 、R b8 、R b9 、R b10 、R b11 、Rb12 、R in P12 b1 、R b2 、R b3 、R b4 、R b5 、R b6 、R b7 、R b8 、R b9 、R b10 、R in P13 b1 、R b2 、R b3 、R b4 、R b5 、R b6 、R b7 、R b8 、R b9 、R b10 、R in P14 b1 、R b2 、R b3 、R b4 、R b5 、R b6 、R b7 、R b8 、R b9 、R b10 is independently selected from any one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C30 heteroaralkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C1-C30 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1-C30 alkoxy or substituted or unsubstituted C6-C30 aryloxy, and exists independently or two adjacent ones are connected to form ring D, and the ring D has the same defined range as above, wherein one or at least two non-adjacent methylene groups in the substituted or unsubstituted C1-C30 alkyl are optionally independently replaced by -O- or -S-.

[0058] Preferably, P1 is selected from any one of the following substituted or unsubstituted groups:

[0059]

[0060]

[0061] Wherein the substituted substituent is selected from any one of deuterium, halogen, cyano, C1-C12 alkyl, C1-C12 alkoxy or C6-C12 aryl.

[0062] Preferably, the N1 is selected from the P1-substituted structure A, and the structure of the N1 is shown as 1-306 in the following table.

[0063]

[0064]

[0065]

[0066] Preferably, the H1 is selected from any one of the following compounds:

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076] Preferably, the triplet energy level of the H1 is higher than that of the N1.

[0077] Preferably, the thickness of the first layer is 1-200 nm.

[0078] Preferably, the thickness of the second layer is 1-100 nm.

[0079] Among them, the thickness of the first layer can be 1 nm, 20 nm, 40 nm, 60 nm, 80 nm, 100 nm, 120 nm, 140 nm, 160 nm, 180 nm or 200 nm, etc., and the thickness of the second layer can be 1 nm, 10 nm, 20 nm, 30 nm, 40 nm, 50 nm, 60 nm, 70 nm, 80 nm, 90 nm or 100 nm, etc., but is not limited to the above-listed values, and other unlisted values within the above numerical range are equally applicable.

[0080] Preferably, the H1 is prepared by a preparation method including the following steps: reacting a compound H1’ with to obtain the compound H1. The reaction formula is as follows:

[0081]

[0082] wherein R 1 -R 16 , Ar 1 , Ar 2 , L 1 , L 2 , L 3 , Y have the same defined ranges as above, and in the compound H1’, at least one of R 1 -R 16 is a halogen.

[0083] Preferably, the N1 is prepared by a preparation method including the following steps: mixing and reacting to obtain the compound N1. The reaction formula is as follows:

[0084]

[0085] wherein R a1 -R a8 , X 2 -X 6 have the same defined ranges as above, and X is selected from halogens.

[0086] The above-mentioned halogens may include fluorine, chlorine, bromine or iodine. An alkyl group refers to a monovalent substituent derived from a straight-chain or branched-chain saturated hydrocarbon having 1 to 30 carbon atoms, including but not limited to methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl or hexyl, etc.; a cycloalkyl group refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 30 carbon atoms, including but not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl or adamantyl, etc.; an alkenyl group refers to a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having at least one carbon-carbon double bond and having 2 to 30 carbon atoms, including but not limited to vinyl, allyl, isopropenyl or 2-butenyl, etc.; an alkynyl group refers to a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having at least one carbon-carbon triple bond and having 2 to 30 carbon atoms, including but not limited to ethynyl, 2-propynyl, etc.; an aryl group and an arylene group include monocyclic, polycyclic or fused-ring aryl groups, and the rings may be interrupted by non-aromatic units, including but not limited to phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthryl, indenyl, triphenylene, pyrenyl, tetracenyl, perylenyl, chrysenyl, tetrabenzo[a,c,g,i]fluorene, fluoranthenyl or spirobifluorenyl, etc., and their derivatives, etc.; a heteroaryl group and a heteroarylene group include monocyclic, polycyclic or fused-ring aryl groups, and the rings may be interrupted by non-aromatic units, including but not limited to furyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuryl, benzothienyl, isobenzofuryl, dibenzofuryl, dibenzothienyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl or dihydroacridinyl, etc., and their derivatives, etc.; an aryloxy group refers to a monovalent substituent represented by RO-, where R represents an aryl group having 6 to 30 carbon atoms, including but not limited to phenoxy, naphthoxy or diphenoxy, etc.; an arylamine refers to an amine substituted by an aryl group having 6 to 30 carbon atoms; a heteroarylamine refers to an amino group substituted by an aryl group or a heterocyclic group having 3 to 30 carbon atoms; an aromatic ring refers to an aromatic ring, which may be monocyclic, polycyclic or fused-ring; a heterocyclic ring includes an aliphatic heterocyclic ring and an aromatic heterocyclic ring, and the heterocyclic ring may be monocyclic, polycyclic or fused-ring; a hydrogen atom includes protium, deuterium or tritium; when two adjacent groups are connected to form a ring, it means that two substituents at adjacent positions in the same six-membered ring or adjacent six-membered rings can be connected to each other by a chemical bond to form a ring, and the specific ring-forming method is not limited.

[0087] Preferably, the aryl group is selected from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl or spirobifluorenyl.

[0088] Preferably, the heteroaryl group is selected from dibenzofuranyl, dibenzothiophenyl, carbazolyl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthimidazolyl, naphthoxazolyl, naphthothiazolyl, phenanthrimidazolyl, phenanthroxazolyl, phenanthrothiazolyl, quinoxalinyl, quinazolinyl, indolocarbazolyl, indolofluorene, benzothiophenopyrazinyl, benzothiophenopyrimidinyl, benzofuropyrazinyl, benzofuropyrimidinyl, indolopyrazinyl, indolopyrimidinyl, indenopyrazinyl, indenopyrimidinyl, spiro(fluorene-9,1'-indene)pyrazinyl, spiro(fluorene-9,1'-indene)pyrimidinyl, benzofurocarbazolyl or benzothiophenocarbazolyl.

[0089] In a second aspect, the present invention provides the use of the combination material as described above in the preparation of an optical device.

[0090] Preferably, the optical device is any one of an organic electroluminescent device, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quenching device, a light emitting electrochemical cell, an organic laser diode or an organic photoreceptor.

[0091] In a third aspect, the present invention provides an organic light emitting diode, comprising an anode and a cathode facing each other, and an organic layer disposed between the anode and the cathode, wherein the composition of the organic layer comprises the combination material as described above.

[0092] Preferably, the organic layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer which are sequentially stacked from the anode side to the cathode side.

[0093] Preferably, the hole transport layer includes a first hole transport layer and a second hole transport layer which are sequentially stacked.

[0094] Preferably, the material of the hole transport layer includes the H1.

[0095] Preferably, the material of the light emitting layer includes a host material and a guest material, and the host material includes the N1.

[0096] Preferably, the host material comprises at least two different types of N1, and the difference in thermal decomposition temperature between the two different types of N1 is not greater than 20 °C, such as 20 °C, 15 °C, 10 °C or 5 °C, etc., but not limited to the values listed above. Other unlisted values within the above numerical range are equally applicable. Preferably 10 °C, more preferably 5 °C.

[0097] Preferably, the guest material comprises a phosphorescent dopant, and the phosphorescent dopant comprises a complex containing Ir or Pt.

[0098] In a fourth aspect, the present invention also provides an organic electroluminescent device, which includes the organic light-emitting diode as described above.

[0099] Compared with the prior art, the present invention has the following beneficial effects:

[0100] The combination material provided by the present invention can improve the driving voltage of the organic electroluminescent device. The prepared organic electroluminescent device has high current efficiency, longer service life and high brightness. Detailed Embodiments

[0101] To further elaborate on the technical means and effects adopted by the present invention, the following further illustrates the technical solutions of the present invention in conjunction with the preferred embodiments of the present invention. However, the present invention is not limited to the scope of the embodiments.

[0102] Example 1 Synthesis of Compound 1

[0103]

[0104] Into a 100 ml three-necked flask, nitrogen was introduced, and compound 1-A (2.59 g, 0.01 mol), compound 1-B (4.6 g, 0.01 mol), sodium tert-butoxide (0.02 mol), tris(dibenzylideneacetone)dipalladium(0) (0.2 mmol), 50% tris(tert-butyl)phosphine solution (0.8 mmol) and 50 ml of toluene were added, and then refluxed and stirred. After cooling to 25 °C, the organic layer was extracted with ethyl acetate and H2O. The extracted organic layer was dried over MgSO4 and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (DCM / hexane), and then recrystallized and purified using a mixed solvent of DCM / acetone to obtain compound 1 (4.60 g, yield: 72%).

[0105] MS (MALDI-TOF) m / z: 639 [M] + 。

[0106] Example 2 Synthesis of Compound 2

[0107]

[0108] Replace Compound 1-A in Example 1 with an equal amount of 2-A and Compound 1-B with an equal amount of 2-B, and the rest is the same as in Example 1. Finally, Compound 2 (4.84 g, yield: 65%) was obtained.

[0109] MS (MALDI-TOF) m / z: 744 [M] + 。

[0110] Synthesis of Compound 3 in Example 3

[0111]

[0112] Replace Compound 1-A in Example 1 with an equal amount of 3-A and Compound 1-B with an equal amount of 3-B, and the rest is the same as in Example 1. Finally, Compound 3 (5.26 g, yield: 73%) was obtained.

[0113] MS (MALDI-TOF) m / z: 721 [M] + 。

[0114] Synthesis of Compound 4 in Example 4

[0115]

[0116] Replace Compound 1-A in Example 1 with an equal amount of 4-A and Compound 1-B with an equal amount of 4-B, and the rest is the same as in Example 1. Finally, Compound 4 (5.18 g, yield: 75%) was obtained.

[0117] MS (MALDI-TOF) m / z: 691 [M] + 。

[0118] Synthesis of Compound 5 in Example 5

[0119]

[0120] Replace Compound 1-A in Example 1 with an equal amount of 5-A and Compound 1-B with an equal amount of 5-B, and the rest is the same as in Example 1. Finally, Compound 5 (5.64 g, yield: 73%) was obtained.

[0121] MS (MALDI-TOF) m / z: 773 [M] + 。

[0122] Synthesis of Compound 6 in Example 6

[0123]

[0124] Replace Compound 1-A in Example 1 with an equal amount of 6-A, and replace Compound 1-B with an equal amount of 6-B. The rest is the same as in Example 1. Finally, Compound 6 (4.95 g, yield: 65%) was obtained.

[0125] MS (MALDI-TOF) m / z: 761 [M] + 。

[0126] Synthesis of Compound 7 in Example 7

[0127]

[0128] Replace Compound 1-A in Example 1 with an equal amount of 7-A, and replace Compound 1-B with an equal amount of 7-B. The rest is the same as in Example 1. Finally, Compound 7 (5.13 g, yield: 71%) was obtained.

[0129] MS (MALDI-TOF) m / z: 723 [M] + 。

[0130] Synthesis of Compound 8 in Example 8

[0131]

[0132] Replace Compound 1-A in Example 1 with an equal amount of 8-A, and replace Compound 1-B with an equal amount of 8-B. The rest is the same as in Example 1. Finally, Compound 8 (5.73 g, yield: 73%) was obtained.

[0133] MS (MALDI-TOF) m / z: 785 [M] + 。

[0134] Synthesis of Compound R156 in Example 9

[0135]

[0136] Add R156-1 (2.17 g, 0.01 mol), R156-2 (2.67 g, 0.01 mol), sodium tert-butoxide (0.02 mol), xphos (0.5 mmol), and 30 mL of xylene to a 100 mL three-necked flask. Protect with nitrogen, then add palladium tetrakis(triphenylphosphine) (0.5 mmol), and protect with nitrogen again. Raise the temperature to 140 °C and stir for 4 hours. Cool to 25 °C. After rotary evaporation of the organic phase, purify by column chromatography (PE:EA = 4:1 - 2:1) to obtain the crude product of Compound R156. Then, slurry it three times with 80 mL of xylene and 80 mL of tetrahydrofuran each to obtain Compound R156 (3.49 g, yield 78%).

[0137] MS (MALDI-TOF) m / z: 448 [M] + 。

[0138] Synthesis of Compound R10 in Example 10

[0139]

[0140] Take a 100 mL two-necked round-bottom flask, place a magnetic stir bar and connect a reflux condenser. After drying, fill it with nitrogen. First, add intermediate R10-1 (3.69 g, 0.01 mol), o-bromonitrobenzene (0.01 mol), potassium carbonate (0.015 mol), ethanol (5 mL), water (5 mL), toluene (30 mL), and tetrakis(triphenylphosphine)palladium (0.5 mmol) respectively. The mixture is refluxed for 12 hours; after the reaction, it is cooled to 25 °C, water is added to the reaction system, and it is extracted with dichloromethane. The obtained extract is successively dried over magnesium sulfate, filtered, and concentrated by rotary evaporation; the crude product is purified by chromatography (ethyl acetate / hexane, 1 / 10) to obtain R10-2 (2.29 g, yield 63%).

[0141] Take a 100 mL two-necked round-bottom flask, place a magnetic stir bar and connect a reflux condenser. After drying, fill it with nitrogen. First, add R10-2 (3.64 g, 0.01 mol), triethyl phosphite (0.01 mol), and 1,2-dichlorobenzene (40 mL) respectively, and then heat the reaction at 180 °C for 12 hours; after the reaction is completed, it is cooled to 25 °C, the reaction system is concentrated, and the crude product is purified by chromatography (ethyl acetate / hexane, 1 / 10) to obtain intermediate R10-3 (2.32 g, yield 70%).

[0142] Replace compound R156-1 in Example 9 with an equal amount of R10-3 and compound R156-2 with an equal amount of R10-4, and the rest is the same as in Example 9. Finally, compound R10 (4.13 g, yield 77%) is obtained

[0143] MS (MALDI-TOF) m / z: 536 [M] + 。

[0144] Synthesis of Compound R44 in Example 11

[0145]

[0146] Replace compound R10-1 in Example 10 with an equal amount of R44-1, and the rest is the same as in Example 10 to obtain compound R44-2 (2.04 g, yield 67%);

[0147] Replace the compound R10-2 in Example 10 with an equal amount of R44-2, and keep the rest the same as in Example 10 to obtain compound R44-3 (1.86 g, yield 68%);

[0148] Replace the compound R10-3 in Example 10 with an equal amount of R44-3 and the compound R10-4 with an equal amount of R44-4, and keep the rest the same as in Example 10 to obtain compound R44 (4.15 g, yield 75%).

[0149] MS (MALDI-TOF) m / z: 553 [M] + 。

[0150] Synthesis of Compound R85 in Example 12

[0151]

[0152] Replace the compound R10-1 in Example 10 with an equal amount of R85-1, and keep the rest the same as in Example 10 to obtain compound R85-2 (2.41 g, yield 66%);

[0153] Replace the compound R10-2 in Example 10 with an equal amount of R85-2, and keep the rest the same as in Example 10 to obtain compound R85-3 (2.26 g, yield 68%);

[0154] Replace the compound R10-3 in Example 10 with an equal amount of R85-3 and the compound R10-4 with an equal amount of R85-4, and keep the rest the same as in Example 10 to obtain compound R85 (4.64 g, yield 74%).

[0155] MS (MALDI-TOF) m / z: 627 [M] + 。

[0156] Synthesis of Compound R154 in Example 13

[0157]

[0158] Replace the compound R10-1 in Example 10 with an equal amount of R154-1, replace o-bromonitrobenzene with an equal amount of R154-2, and keep the rest the same as in Example 10 to obtain compound R154-3 (2.49 g, yield 61%).

[0159] Replace the compound R10-3 in Example 10 with an equal amount of R154-3 and the compound R10-4 with an equal amount of R154-4, and keep the rest the same as in Example 10 to obtain compound R154 (4.92 g, yield 77%).

[0160] MS (MALDI-TOF) m / z: 639 [M] + 。

[0161] Synthesis of Compound R220 in Example 14

[0162]

[0163] Replace the compound R10-1 in Example 10 with an equal amount of R220-1, and the rest is the same as in Example 10 to obtain compound R220-2 (2.44 g, yield 67%);

[0164] Replace the compound R10-2 in Example 10 with an equal amount of R220-2, and the rest is the same as in Example 10 to obtain compound R220-3 (2.32 g, yield 70%);

[0165] Replace the compound R10-3 in Example 10 with an equal amount of R220-3 and the compound R10-4 with an equal amount of R220-4, and the rest is the same as in Example 10 to obtain compound R220 (3.81 g, yield 71%).

[0166] MS (MALDI-TOF) m / z: 536 [M] + 。

[0167] Synthesis of Compound R5 in Example 15

[0168]

[0169] Take a 100 mL two-necked round-bottom flask, place a stir bar in it and connect a reflux tube above. After drying, fill it with nitrogen; first add o-nitrophenylboronic acid (1.67 g, 0.01 mol), o-bromoiodobenzene (2.82 g, 0.01 mol), potassium carbonate (0.015 mol), ethanol (2 mL), water (2 mL), toluene (2 mL), and tetrakis(triphenylphosphine)palladium (0.5 mmol) respectively, then heat to reflux and react for 12 hours. After the reaction is completed, cool to 25 °C; add 80 mL of water to quench the reaction, and extract with dichloromethane (3 × 80 mL); the obtained extract is sequentially dried with magnesium sulfate, filtered and rotary evaporated; the crude product is purified by chromatography (ethyl acetate / hexane, 1 / 10) to obtain R5-1 (1.75 g, yield 63%).

[0170] Take a 100 mL two-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. After drying, fill it with nitrogen. First, add R5-1 (2.77 g, 0.01 mol), bis(pinacolato)diboron (0.01 mol), potassium acetate (0.02 mol), dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) (0.25 mmol), and 1,4-dioxane (40 mL) respectively. React at 120 °C for 8 hours. After the reaction is completed, cool to 25 °C, quench with water, extract with dichloromethane (100 mL × 3). Dry the extract with anhydrous magnesium sulfate, rotary evaporate, and separate the crude product by silica gel column chromatography to obtain R5-2 (1.98 g, yield 61%).

[0171] Take a 100 mL two-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. After drying, fill it with nitrogen. First, add intermediate R5-2 (3.25 g, 0.01 mol), 1,8-dibromonaphthalene (0.01 mol), potassium carbonate (0.015 mol), ethanol (5 mL), water (5 mL), toluene (30 mL), and tetrakis(triphenylphosphine)palladium (0.5 mmol) respectively. Reflux the mixture for 12 hours. After the reaction, cool to 25 °C, add water to the reaction system, extract with dichloromethane. The obtained extract is successively dried with magnesium sulfate, filtered, and rotary evaporated. Purify the crude product by chromatography (ethyl acetate / hexane, 1 / 10) to obtain R5-3 (2.26 g, yield 56%).

[0172] Take a 100 mL two-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. After drying, fill it with nitrogen. First, add R5-3 (4.03 g, 0.01 mol), dichloro(bis(tricyclohexylphosphine))palladium (0.5 mmol), pivalic acid (0.02 mol), cesium carbonate (0.02 mol), and dimethylacetamide (40 mL) respectively. Stir at 120 °C for 10 hours. After the reaction is completed, cool to 25 °C, concentrate the reaction system, and purify the crude product by chromatography (ethyl acetate / hexane, 1 / 10) to obtain R5-4 (2.55 g, yield 79%).

[0173] Take a 100 mL two-necked round-bottom flask, place a magnetic stir bar in it and connect a reflux condenser above. After drying, fill it with nitrogen. First, add R5-4 (3.23 g, 0.01 mol), triethyl phosphite (0.01 mol), and 1,2-dichlorobenzene (30 mL) respectively. Then heat the reaction at 180 °C for 12 hours. After the reaction is completed, cool to 25 °C, concentrate the reaction system, and purify the crude product by chromatography (ethyl acetate / hexane, 1 / 10) to obtain intermediate R5-5 (2.07 g, yield 71%).

[0174] Replace the compound R156-1 in Example 9 with an equal amount of R5-5, and replace the compound R156-2 with an equal amount of R10-4. The rest is the same as in Example 9. Finally, compound R5-5 (3.86 g, yield 78%) is obtained.

[0175] MS (MALDI-TOF) m / z: 495 [M] + 。

[0176] Synthesis of Compound R142 in Example 16

[0177]

[0178] Replace the compound o-bromoiodobenzene in Example 15 with an equal amount of R142-1. The rest is the same as in Example 15 to obtain compound R142-2 (1.99 g, yield 61%);

[0179] Replace the compound R5-1 in Example 15 with an equal amount of R142-2. The rest is the same as in Example 15 to obtain compound R142-3 (2.25 g, yield 60%);

[0180] Replace the compound R5-2 in Example 15 with an equal amount of R142-3. The rest is the same as in Example 15 to obtain compound R142-4 (2.18 g, yield 54%);

[0181] Replace the compound R5-3 in Example 15 with an equal amount of R142-4. The rest is the same as in Example 15 to obtain compound R142-5 (2.49 g, yield 77%);

[0182] Replace the compound R5-4 in Example 15 with an equal amount of R142-5. The rest is the same as in Example 15 to obtain compound R142-6 (2.12 g, yield 73%);

[0183] Replace the compound R5-5 in Example 15 with an equal amount of R142-6 and replace the compound R10-4 with an equal amount of R142-7. The rest is the same as in Example 15 to obtain compound R142 (3.35 g, yield 67%).

[0184] MS (MALDI-TOF) m / z: 500 [M] + 。

[0185] Synthesis of Compound R307 in Example 17

[0186]

[0187] Replace the compound R156-1 in Example 9 with an equal amount of R307-1, and replace the compound R156-2 with an equal amount of R307-2. The rest is the same as in Example 9. Finally, compound R307 (4.39 g, yield 74%) is obtained.

[0188] MS (MALDI-TOF) m / z: 593 [M] + 。

[0189] The following Application Examples 1-16 and Comparative Application Examples 1-4 respectively provide an OLED having the following structure stacked in sequence: substrate (indium tin oxide (ITO)-coated glass substrate) / hole injection layer (HIL) / hole transport layer (HTL-1) / hole transport auxiliary layer (HTL-2) / emitting layer (EML) / electron transport layer (ETL) / optional electron injection layer (EIL), and finally a cathode.

[0190] The materials used are as follows:

[0191]

[0192] The preparation steps are as follows:

[0193] 1) Substrate cleaning:

[0194] Ultrasonically treat the glass substrate coated with the ITO transparent electrode in an aqueous cleaning agent (composition and concentration of the aqueous cleaning agent: 10 wt% ethylene glycol solvent, 1 wt% triethanolamine), rinse in deionized water, ultrasonically degrease in an acetone-ethanol mixed solvent (volume ratio 1:1), bake in a clean environment until all moisture is removed, and then clean with ultraviolet light and ozone;

[0195] 2) Evaporation:

[0196] Place the above-mentioned glass substrate with the anode in a vacuum chamber, evacuate to between 1×10 -6 to 2×10 -4 Pa, and vacuum evaporate the hole injection layer material in a co-evaporation manner on the above-mentioned anode layer film, where the rates of PD and DNTPD are adjusted by mass ratio, the total evaporation rate is 0.1 nm / s, and the evaporation thickness is 10 nm;

[0197] 3) Evaporate the first hole transport layer on top of the hole injection layer, with an evaporation rate of 0.1 nm / s and an evaporation film thickness of 60 nm;

[0198] 4) Evaporate the second hole transport layer on top of the first hole transport layer, with an evaporation rate of 0.1 nm / s and an evaporation film thickness of 20 nm;

[0199] 5) Evaporate the light-emitting layer on top of the hole transport layer, and vacuum-evaporate the host material and the guest material of the light-emitting layer in a co-evaporation manner. Adjust the evaporation rate according to the mass ratio of the host material to the guest material, with the total evaporation rate being 0.1 nm / s and the total film thickness being 30 nm;

[0200] 6) Vacuum-evaporate an electron transport layer on top of the light-emitting layer, adjust the evaporation rate according to the mass ratio of the compound BPhen to LiQ, with the total evaporation rate being 0.1 nm / s and the total film thickness being 30 nm;

[0201] 7) Vacuum-evaporate an electron injection layer on top of the electron transport layer, with the evaporation rate being 0.05 nm / s and the total film thickness being 1 nm;

[0202] 8) Evaporate the cathode on top of the electron injection layer. For metal Al, the total evaporation rate is 0.1 nm / s and the total film thickness is 100 nm.

[0203] The composition of each application example and the comparative application examples is as follows:

[0204]

[0205]

[0206]

[0207] Performance test:

[0208] Perform drive voltage, current efficiency, and lifetime tests on the OLEDs provided in the above application examples 1-16 and comparative application examples 1-4. The test method is as follows:

[0209] Instrumentation: PR 650 spectral scanning luminance meter, Keithley K 2400 digital source meter system;

[0210] Test conditions: Current density is 20 mA / cm 2 , 25 °C.

[0211] Lifetime test: Record the time (in hours) when the device brightness drops to 95% of the original brightness.

[0212] The test results are as follows:

[0213]

[0214] The above data shows that the combination materials provided by the present invention, when applied to organic electroluminescent devices, have higher current efficiency and longer service life under the same drive voltage and current density, demonstrating excellent performance. In compound H1, Y is selected from CR Y1 R Y2 and R Y1 、RY2 With R 14 and R 13 The luminescence effect connected to form a benzene ring is higher.

[0215] The applicant declares that the present invention uses the above embodiments to illustrate the composite material of the present invention, its preparation method and application. However, the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvement to the present invention, the equivalent replacement of each raw material of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc. all fall within the protection scope and the disclosure scope of the present invention.

[0216] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the specific details in the above embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solution of the present invention, and these simple modifications all belong to the protection scope of the present invention.

[0217] In addition, it should be noted that, in the case of no contradiction, the various specific technical features described in the above specific embodiments can be combined in any suitable way. In order to avoid unnecessary repetition, the present invention will not separately describe various possible combination methods.

Claims

1. A composite material, characterized in that, The composite material includes a first layer and a second layer which are stacked in sequence; The composition of the first layer includes H1, and the composition of the second layer includes N1; The structures of H1 and N1 are shown in Formula I: where Y is selected from O, S or CR Y1 R Y2 ; Said R Y1 and R Y2 are independently selected from C1-C30 alkyl; The said R Y1 , R Y2 exist independently or are connected with R 14 or / and R 13 to form ring A; The said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 are independently selected from any one of hydrogen, deuterium, halogen, C1-C30 alkyl, and C6-C30 aryl, and at least one of R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 is selected from at least Said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 exist independently or the adjacent two are connected to form ring B; Ring A and Ring B are selected from substituted or unsubstituted benzene rings; Said L 1 、L 2 、L 3 are independently selected from a single bond or a C6-C30 arylene group; The Ar 1 and Ar 2 are independently selected from substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C2-C60 heteroaryl; The said X 1 is selected from N or Cl X1 R X1 , X 2 is selected from N or Cl X2 R X2 , X 3 is selected from N or Cl X3 R X3 , X 4 is selected from N or Cl X4 R X4 , X 5 is selected from N or Cl X5 R X5 , X 6 is selected from N or Cl X6 R X6 ; The R X1 , R X2 , R X3 , R X4 , R X5 , R X6 is independently selected from any one of P1, hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C2-C60 heteroaryl, and the structure of the P1 is shown in Formula II: The said L X1 、L X2 、L X3 、L X4 、L X5 、L X6 are independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group; The said L X1 R X1 、L X2 R X2 、L X3 R X3 、L X4 R X4 、L X5 R X5 、L X6 R X6 exist independently or two adjacent ones are connected to form a ring C; Ring C is selected from substituted or unsubstituted benzene rings; The said R a1 , R a2 , R a3 , R a4 , R a5 , R a6 , R a7 , R a8 are independently selected from hydrogen, deuterium, substituted or unsubstituted C2-C30 heteroaryl; The said R a1 、R a2 、R a3 、R a4 、R a5 、R a6 、R a7 、R a8 exist independently or two adjacent ones are connected to form a ring D; Ring D is selected from substituted or unsubstituted C6-C30 aryl groups or substituted or unsubstituted C2-C30 heteroaryl groups.

2. The composite material according to claim 1, wherein Said R 3 、R 4 、R 5 、R 6 At least one of them is selected from 3. The composite material according to claim 2, wherein Said R 4 or R 6 at least one of which is selected from 4. The composite material according to claim 3, characterized in that, The said L 1 , L 2 , L 3 is independently selected from any one of a single bond, a phenylene group, a biphenylene group, and a naphthylene group.

5. The composite material according to claim 4, wherein Said Ar 1 and Ar 2 are independently selected from the following substituted or unsubstituted groups: Any one of the above, wherein the substituent of the substitution is selected from deuterium.

6. The composite material according to claim 5, wherein N1 is selected from any one of N2, N3, N4 or N5, and the structures of N2, N3, N4 and N5 are shown in Formula III: R in the N2 x2 、R x4 、R x6 have the same scope of definition as claim 1, and among R x2 、R x4 、R x6 only one is P1; R in the N3 x2 and R x3 and R x4 and R x6 have the same defined scope as claim 1, and among R x2 and R x3 and R x4 and R x6 only one is P1; R in the N4 x2 , R x6 , R x7 , R x8 , R x9 , R x10 is independently selected from any one of P1, hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl, or substituted or unsubstituted C2-C60 heteroaryl, and only one of R x2 , R x6 is P1; R in the N5 x1 and R x6 and R x7 and R x8 and R x9 and R x10 are independently selected from any one of P1, hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl or substituted or unsubstituted C2-C60 heteroaryl, and among R x1 and R x6 only one is P1.

7. The composite material according to claim 6, wherein N1 is selected from any one of the following substituted or unsubstituted groups substituted by P1: wherein represents a site connected to P1, and the substituent of the substitution is selected from deuterium.

8. The composite material according to claim 7, wherein, The said L X1 , L X2 , L X3 , L X4 , L X5 , L X6 are independently selected from single bonds.

9. The composite material according to claim 8, wherein P1 is selected from any one of the products formed by fusing any two adjacent ones of P2, P3, P4 or R in P1 with P10, and the structures of P2, P3, P4 and P10 are as shown in Formula IV: a1 -R a8 ​ Among them, R in P2 a1 and R a2 and R a5 and R a6 and R a7 and R a8 and R a9 and R a10 and R a11 and R a12 and R in P3 a1 and R a4 and R a5 and R a6 and R a7 and R a8 and R a9 and R a10 and R a11 and R a12 and R in P4 a3 and R a4 and R a5 and R a6 and R a7 and R a8 and R a9 and R a10 and R a11 and R a12 and R in P10 b1 and R b2 and R b3 and R b4 are independently selected from hydrogen or deuterium, and exist independently or the adjacent two are connected to form ring D, and ring D has the same defined scope as that in claim 1, and * in P10 refers to the fusion site; X b is selected from any one of O, S or NR Xb3 ; R Xb3 is selected from phenyl, biphenyl, naphthyl, phenyl-substituted naphthyl, naphthyl-substituted phenyl, pyridyl, pyridyl-substituted phenyl or phenyl-substituted pyridyl.

10. The composite material according to claim 9, wherein, R in P1 a1 -R a8 The product of any two adjacent ones of them and P10 is selected from any one of P12, P13 or P14. The structures of P12, P13 and P14 are shown in Formula V: Among them, R in the P12 b1 and R b2 and R b3 and R b4 and R b5 and R b6 and R b7 and R b8 and R b9 and R b10 and R in the P13 b1 and R b2 and R b3 and R b4 and R b5 and R b6 and R b7 and R b8 and R b9 and R b10 and R in the P14 b1 and R b2 and R b3 and R b4 and R b5 and R b6 and R b7 and R b8 and R b9 and R b10 are independently selected from hydrogen or deuterium.

11. The composite material according to claim 10, wherein P1 is selected from any one of the following substituted or unsubstituted groups: Wherein the substituent of the substitution is selected from deuterium.

12. The composite material according to claim 11, wherein N1 is selected from the structure A substituted by P1, and the structure of N1 is shown in the following table.

13. The composite material according to claim 12, characterized in that, H1 is selected from any one of the following compounds:

14. The composite material according to claim 13, wherein The triplet energy level of H1 is higher than the triplet energy level of N1.

15. The composite material according to claim 14, characterized in that, The thickness of the first layer is 1-200 nm.

16. The composite material according to claim 15, wherein The thickness of the second layer is 1-100 nm.

17. The application of the composite material according to any one of claims 1-16 in the preparation of an optical device.

18. Use of the composite material according to claim 17 in the preparation of an optical device, characterized in that, The optical device includes any one of an organic electroluminescent device, an organic field effect transistor, an organic thin film transistor, an organic light emitting transistor, an organic integrated circuit, an organic solar cell, an organic field quenching device, a light-emitting electrochemical cell, an organic laser diode or an organic photoreceptor.

19. An organic electroluminescent diode includes an anode and a cathode facing each other, and an organic layer disposed between the anode and the cathode, characterized in that, The composition of the organic layer contains the composite material according to any one of claims 1-16.

20. The organic electroluminescent diode according to claim 19, wherein The organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer and an electron injection layer which are stacked in sequence from the anode side to the cathode side.

21. The organic electroluminescent diode according to claim 20, characterized in that, The hole transport layer includes a first hole transport layer and a second hole transport layer which are stacked in sequence.

22. The organic electroluminescent diode according to claim 21, wherein, The material of the hole transport layer includes H1.

23. The organic electroluminescent diode according to claim 22, wherein, The material of the light-emitting layer includes a host material and a guest material, and the host material includes N1.

24. The organic electroluminescent diode according to claim 23, wherein The host material includes at least two different N1s, and the difference in thermal decomposition temperature between the two different N1s is not greater than 20 °C.

25. The organic electroluminescent diode according to claim 24, wherein, The difference in thermal decomposition temperature between the two different N1s is 10 °C.

26. The organic electroluminescent diode according to claim 24, wherein The difference in thermal decomposition temperature between the two different N1s is 5 °C.

27. The organic electroluminescent diode according to claim 24, wherein The guest material includes a phosphorescent dopant, and the phosphorescent dopant includes a complex containing Ir or Pt.

28. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes the organic electroluminescent diode according to any one of claims 19-27.

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