CN111933818A

CN111933818A - Organic light-emitting device

Info

Publication number: CN111933818A
Application number: CN202010805413.2A
Authority: CN
Inventors: 韩春雪; 周雯庭; 孙月
Original assignee: Changchun Haipurunsi Technology Co Ltd
Current assignee: Changchun Haipurunsi Technology Co Ltd
Priority date: 2020-08-12
Filing date: 2020-08-12
Publication date: 2020-11-13

Abstract

The invention provides an organic light-emitting device, and relates to the technical field of organic photoelectric materials. The triarylamine compound represented by the formula (1) and the heterocyclic compound represented by the formula (2) are selected as the first covering layer and the second covering layer, so that the total reflection loss can be better reduced compared with the combination of two materials with different refractive indexes of a traditional organic light-emitting device with a single covering layer, the luminous efficiency of the organic light-emitting device is improved, the stability and the durability of a film are excellent, and the film does not have absorption in respective wavelength regions of blue, green and red.

Description

Organic light-emitting device

Technical Field

The invention relates to the technical field of organic electroluminescence, in particular to an organic light-emitting device.

Background

Organic Light Emitting Devices (OLEDs) refer to devices in which holes injected from an anode and electrons injected from a cathode are transported and recombined in an organic functional layer to form excitons, which in turn emit photons by radiation. In terms of display, OLEDs have many advantages over the Liquid Crystal Displays (LCDs) that are now popular: (1) thickness can be less than 1mm, 1/3 for LCD screen only, and lighter weight; (2) there is little problem with the angle of visibility. Even if the picture is viewed under a large visual angle, the picture is still undistorted; (3) the structure is solid, no liquid substance exists, and therefore the earthquake-resistant performance is better; (4) the low-temperature characteristic is good, normal display can still be realized at minus 40 ℃, and the LCD cannot realize the normal display; (5) the response time is one thousandth of that of the LCD, and the motion picture is displayed without smearing; (6) the manufacturing process is simple; (7) the luminous efficiency is higher, and the energy consumption is lower than that of an LCD; (8) the method can be applied to miniature display equipment; (9) the display can be manufactured on substrates of different materials and can be made into a flexible display. In recent years, OLEDs have been increasingly used in the display market, and become the most potential panel display technology at present.

The structures of OLEDs are currently mainly divided into two-layer structures according to organic functional layers: the hole transport layer or the electron transport layer itself has a functional layer that carries carriers and emits light; three-layer structure: the hole transport layer, the luminescent layer and the electron transport layer form an organic functional layer of the device; the multilayer structure is formed by adding a hole injection layer, an electron injection layer, a covering layer and the like on the basis of the basic layer. A bottom emission device in which a light emitting area is affected by a pixel circuit due to emission from the bottom and a top emission device in which this problem does not exist are divided according to a light emitting direction. In a top-emitting device, light emitted from the light-emitting layer is reflected and refracted at the interfaces of other organic functional layers, so that a part of the light exists inside the device and only a part of the emitted light can be utilized, which is a large loss.

In order to improve the light extraction efficiency, it has been proposed to provide a cover layer having a high refractive index on the outer side of a translucent electrode having a low refractive index. However, the application of the cladding layer in OLEDs is less at present, and the total reflection loss cannot be reduced well under the condition that the existing organic light emitting device usually uses a single-layer cladding layer, so that the improvement of the light emitting efficiency is not very large.

In general, in the future, the OLED is developed to be a white light device and a full color display device with high efficiency, long lifetime and low cost, but the industrialization process of the technology still faces many key problems, and how to design an organic light emitting device with better performance for adjustment is a problem that needs to be solved urgently by those skilled in the art.

Disclosure of Invention

An object of the present invention is to provide an organic light emitting device in which a first cover layer and a second cover layer made of materials of formulae (1) and (2) are selected for improving device characteristics of the organic light emitting device, particularly for greatly improving light extraction efficiency, the refractive index of the first cover layer is 1.9 or more, the refractive index of the second cover layer is 1.0 or more, total reflection can be reduced by two materials having different refractive indices, and the organic light emitting device has excellent stability and durability of a thin film and does not have absorption in each wavelength region of blue, green, and red. The organic light-emitting device prepared by using the combination mode has good luminous efficiency.

In order to achieve the above object, the first and second capping layers composed of the materials of formulas (1) and (2) were selected and the characteristics of the organic light emitting device were deeply evaluated, solving the above problems. The present invention provides an organic light emitting device comprising an anode electrode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a cathode electrode and a cover layer in this order, wherein the cover layer comprises a first cover layer and a second cover layer, wherein the refractive index of the first cover layer is 1.9 or more and the refractive index of the second cover layer is 1.0 or more in the wavelength range of 400nm to 750nm of light transmitted through the cover layer, the first cover layer contains a triarylamine compound represented by the following formula (1),

the second cover layer contains a heterocyclic compound represented by formula (2),

wherein Ar is₁、Ar₂、Ar₃Independently selected from one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C3-C18 heteroaryl; l is₁、L₂、L₃Independently selected from one of single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C3-C18 heteroarylene;

wherein Ar is₁、Ar₂、Ar₃At least one is one of the groups shown in the following structural formula A-structural formula I:

wherein X, the same or different at each occurrence, is CR or N, wherein at least one X is N;

r is one selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, indolyl, dibenzothienyl, dibenzofuranyl, pyridyl and pyrimidyl;

R₁one selected from the group consisting of methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, dibenzothienyl, dibenzofuranyl, pyridyl, and pyrimidyl;

R₂one selected from the group consisting of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothienyl, dibenzofuranyl;

l is selected from one of a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted terphenylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted fluorenylene and substituted or unsubstituted dibenzothiophenylene;

z is selected from O or S or NR 'wherein R' is selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl;

wherein, X₁Selected from O, S, Si R 'R', Se, CR 'R' or

Y and Z are each independently hydrogen or deuterium, or Y and Z together form a bond, or-W-, wherein W is O, S, Si R "R", CR "R"; x₂The compound is selected from a single bond, O, S or CR ' R ', wherein R ' is selected from one of methyl, ethyl, isopropyl, tert-butyl, phenyl, dibenzofuranyl, dibenzothienyl, furyl, thienyl, benzofuranyl and benzothienyl; r' is selected from one of H, methyl, ethyl, isopropyl, tert-butyl, phenyl, dibenzofuranyl and dibenzothienyl; r' is selected from one of H, methyl, ethyl, isopropyl, tert-butyl, phenyl, dibenzofuranyl and dibenzothienyl;

wherein Ar is₂₁、Ar₂₂Independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C3-C18 heteroaryl or N (Q)₁)(Q₂) One of the groups represented, wherein Q₁And Q₂Independently selected from deuterium, substituted or unsubstituted C1-C8 straight chain or branched chain alkyl, substituted or unsubstituted C5-C10 cycloalkyl, substituted or unsubstituted C6-C25 aryl and substituted or unsubstituted C3-C18 heteroaryl;

m is 0,1 or 2, n is 0,1 or 2, and m + n is more than or equal to 1.

The invention has the beneficial effects that:

the invention provides an organic light-emitting device, which selects a triarylamine compound represented by a formula (1), a first covering layer and a second covering layer formed by a heterocyclic compound represented by a formula (2), wherein the first covering layer and the second covering layer are formed by the heterocyclic compound represented by the formula (1). firstly, compared with the traditional organic light-emitting device with a single covering layer, the combination of two materials with different refractive indexes can better reduce total reflection loss, thereby improving the light-emitting efficiency of the organic light-emitting device, and the film has excellent stability and durability and does not have absorption in respective wavelength regions of blue, green and red;

secondly, the coating material of the invention introduces a heteroaryl structure compound, the intermolecular interaction force is low, so that the evaporation temperature of the material in a vacuum state is generally less than 330 ℃, thereby not only ensuring that the evaporation material is not decomposed in a long time in mass production, but also reducing the deformation influence of the thermal radiation of the evaporation temperature on the evaporation mask plate, causing no loss to the organic light-emitting device, simultaneously effectively blocking water and oxygen in the external environment and protecting the OLED display panel from being corroded by the water and the oxygen.

Detailed Description

The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.

The alkyl group in the present invention refers to a hydrocarbon group formed by dropping one hydrogen atom from an alkane molecule, and may be a straight-chain alkyl group, a branched-chain alkyl group, or a cyclic alkyl group, and preferably has 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl and the like, but is not limited thereto; the branched alkyl group includes, but is not limited to, an isomeric group of isopropyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, an isomeric group of n-hexyl, an isomeric group of n-heptyl, an isomeric group of n-octyl, an isomeric group of n-nonyl, an isomeric group of n-decyl, etc.; the cycloalkyl group includes cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, and the like, but is not limited thereto. The alkyl group is preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group or a 2-adamantyl group.

The aryl group in the present invention refers to a general term of monovalent group remaining after one hydrogen atom is removed from an aromatic nucleus carbon of an aromatic compound molecule, and may be monocyclic aryl group, polycyclic aryl group or condensed ring aryl group, preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 14 carbon atoms. The monocyclic aryl group means an aryl group having only one aromatic ring in the molecule, for example, phenyl group and the like, but is not limited thereto; the polycyclic aromatic group means an aromatic group having two or more independent aromatic rings in the molecule, for example, biphenyl group, terphenyl group and the like, but is not limited thereto; the fused ring aryl group refers to an aryl group in which two or more aromatic rings are contained in a molecule and are fused together by sharing two adjacent carbon atoms, and examples thereof include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirobifluorenyl, and the like. The above aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group (preferably a 2-naphthyl group), an anthryl group (preferably a 2-anthryl group), a phenanthryl group, a pyrenyl group, a perylenyl group, a fluorenyl group, a benzofluorenyl group, a triphenylene group, or a spirobifluorenyl group.

The heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic nucleus carbon atoms in an aryl group with a heteroatom, including but not limited to oxygen, sulfur, nitrogen or phosphorus atom, preferably having 1 to 25 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 3 to 15 carbon atoms, wherein the attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a fused ring heteroaryl group. The monocyclic heteroaryl group includes pyridyl, pyrimidyl, triazinyl, furyl, thienyl, pyrrolyl, imidazolyl and the like, but is not limited thereto; the polycyclic heteroaryl group includes bipyridyl, phenylpyridyl, and the like, but is not limited thereto; the fused ring heteroaryl group includes quinolyl, isoquinolyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, acridinyl, 9, 10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl and the like, but is not limited thereto. The heteroaryl group is preferably a pyridyl group, a pyrimidyl group, a thienyl group, a furyl group, a benzothienyl group, a benzofuryl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a dibenzofuryl group, a dibenzothienyl group, a dibenzofuryl group, a carbazolyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group or a phenoxathiyl group.

The arylene group in the present invention refers to a general term of a divalent group remaining after two hydrogen atoms are removed from an aromatic core carbon of an aromatic compound molecule, and may be a monocyclic arylene group, a polycyclic arylene group or a condensed ring arylene group, and preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 14 carbon atoms. The monocyclic arylene group includes phenylene group and the like, but is not limited thereto; the polycyclic arylene group includes, but is not limited to, biphenylene, terphenylene, and the like; the condensed ring arylene group includes naphthylene, anthrylene, phenanthrylene, fluorenylene, pyrenylene, triphenylene, fluoranthenylene, phenylfluorenylene, and the like, but is not limited thereto. The arylene group is preferably a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenylene group, or a phenylfluorenylene group.

Heteroarylene as used herein refers to the generic term for groups in which one or more of the aromatic core carbons in the arylene group is replaced with a heteroatom, including, but not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably having 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 15 carbon atoms, and the linking site of the heteroarylene group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroarylene group may be a monocyclic heteroarylene group, a polycyclic heteroarylene group, or a fused ring heteroarylene group. The monocyclic heteroarylene group includes a pyridylene group, a pyrimidylene group, a triazinylene group, a furanylene group, a thiophenylene group and the like, but is not limited thereto; the polycyclic heteroarylene group includes bipyridyl idene, phenylpyridyl, etc., but is not limited thereto; the fused ring heteroarylene group includes, but is not limited to, a quinolylene group, an isoquinolylene group, an indolyl group, a benzothiophene group, a benzofuranylene group, a benzoxazolyl group, a benzimidazolylene group, a benzothiazolyl group, a dibenzofuranylene group, a dibenzothiophenylene group, a carbazolyl group, a benzocarbazolyl group, an acridinylene group, a 9, 10-dihydroacridine group, a phenoxazinyl group, a phenothiazinylene group, a phenoxathiin group and the like. The heteroaryl group is preferably a pyridylene group, pyrimidylene group, thienylene group, furylene group, benzothienylene group, benzofuranylene group, benzoxazolyl group, benzimidazolylene group, benzothiazolyl group, dibenzofuranylene group, dibenzothiophenylene group, dibenzofuranylene group, carbazolyl group, acridinylene group, phenoxazinyl group, phenothiazinylene group or phenoxathiin group.

The substituted alkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene as described herein means mono-or poly-substituted with groups independently selected from, but not limited to, deuterium, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted amine, and the like, preferably with groups selected from, but not limited to, deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, benzophenanthryl, perylenyl, pyrenyl, benzyl, fluorenyl, 9-dimethylfluorenyl, dianilino, dimethylamino, carbazolyl, 9-phenylcarbazolyl, acridinyl, furyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, perylene, pyrenyl, benzyl, fluorenyl, 9-dimethylfluorenyl, dimethylamino, carbazolyl, 9-phenylcarbazolyl, acridinyl, furyl, thienyl, benzothienyl, benzoxazolyl, benzimidazol, Mono-or polysubstitution of dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl groups.

The invention provides an organic light-emitting device, which is provided with an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a cathode electrode and a covering layer in sequence, wherein the covering layer comprises a first covering layer and a second covering layer, the refractive index of the first covering layer is 1.9 within the range of 400 nm-750 nm of the wavelength of light penetrating through the covering layerThe second cover layer has a refractive index of 1.0 or more, the first cover layer contains a triarylamine compound represented by the following formula (1),

wherein Ar is₁、Ar₂、Ar₃At least one of which is one of the groups represented by the following structural formulae A to I:

R₁selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, dibenzothiopheneOne of phenyl, dibenzofuranyl, pyridyl and pyrimidyl;

wherein, X₁Selected from O, S, Si R 'R', Se, CR 'R' or

m is 0,1 or 2, n is 0,1 or 2, and m + n is more than or equal to 1.

Preferably, Ar is₁Is one of the following groups:

wherein, Ar is₄、Ar₅、Ar₆、Ar₇、Ar₈、Ar₉、Ar₁₀、Ar₁₁、Ar₁₂、Ar₁₃、Ar₁₄、Ar₁₅、Ar₁₆、Ar₁₇、Ar₁₈、Ar₁₉、Ar₂₀Each independently represents one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, benzothienyl, benzofuranyl, dibenzothienyl and dibenzofuranyl; ar (Ar)₄、Ar₅、Ar₆、Ar₇、Ar₈、Ar₉、Ar₁₀、Ar₁₁、Ar₁₂、Ar₁₃、Ar₁₄、Ar₁₅、Ar₁₆、Ar₁₇、Ar₁₈、Ar₁₉、 Ar₂₀May be the same or different;

R_arepresented by deuterium, methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl or pyridyl;

p is 0,1 or 2;

r is selected from one of methyl, ethyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothienyl and dibenzofuryl;

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

L₁、L₂、L₃independently selected from single bond or one of the following groups:

preferably, Ar is₁One selected from the group shown below:

preferably, Ar is₂、Ar₃Independently selected from one of the following groups:

wherein R is₁₂One selected from methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl and naphthyl;

R₁₃selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridine, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranylOne kind of the material is selected;

L₀one selected from the group consisting of a single bond, phenylene, tolylene, biphenylene, naphthylene, terphenylene, dibenzofuranylene, fluorenylene, dibenzothiophenylene;

e is selected from an integer of 0 to 2;

a is selected from an integer of 0 to 3;

c is an integer from 0 to 4;

b is an integer from 0 to 5;

d is an integer from 0 to 7;

f is an integer from 0 to 9.

more preferably, Ar₂、Ar₃Independently selected from one of the following groups:

preferably, the formula (1) is selected from any one of the following chemical structures:

preferably, the formula (2) is one selected from the following formulae (2) -1 to (2) -14:

preferably, Ar is₂₁、Ar₂₂Independently selected from n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted indenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted indolyl, Substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolylSubstituted or unsubstituted quinazolinyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted benzospirofluorenyl, substituted or unsubstituted phenylfluorenyl, wherein substituted phenyl, substituted naphthyl, substituted anthracenyl, substituted phenanthrenyl, substituted triphenylenyl, substituted pyrenyl, substituted perylenyl, substituted indenyl, substituted pyrrolyl, substituted imidazolyl, substituted oxazolyl, substituted thiazolyl, substituted pyridyl, Substituted pyrimidinyl, substituted triazinyl, substituted benzofuranyl, substituted benzothienyl, substituted indolyl, substituted quinolinyl, substituted isoquinolinyl, substituted quinazolinyl, substituted benzimidazolyl, substituted benzoxazolyl, substituted acridinyl, substituted phenazinyl, substituted phenothiazinyl, substituted phenoxazinyl, substituted fluorenyl, substituted carbazolyl, substituted dibenzofuranyl, substituted dibenzothienyl, substituted spirofluorenyl, substituted benzospirofluorenyl, substituted phenylfluorenyl, wherein the substituent in the substituted phenylfluorenyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, Phenyl, biphenyl, terphenyl, naphthyl, pyridyl,

or from N (Q)₁)(Q₂) One of the groups represented, wherein Q₁And Q₂Independently selected from deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluorenyl, indene, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, isoheptyl, 2-adamantyl, biphenyl, terphenyl, naphthylOne of a group selected from the group consisting of a phenyl group, a pyrenyl group, a perylene group, a fluoranthenyl group, a triphenylene group, a pyridyl group, a pyranyl group, a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, an imidazolinyl group, a pyrazolyl group, a pyrazolinyl group, a pyridazinyl group, a pyrazinyl group, a piperidyl group, a piperazinyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl.

Preferably, N (Q)₁)(Q₂) The group represented is dimethylamino, diethylamino, diadamantylamino, diphenylamino, ditolylamino, diphenylamino, dinaphthylamino, dinefluorenylamino, dipyridylamino, di (dibenzothienyl) amino, di (dibenzofuranyl) amino, di (9-phenylcarbazolyl) amino, dibenzothienyl amino, dibenzooxazolylamino, dibenzothiazolyl amino, dibenzoimidazolyl amino, or bipyrimidinylamino.

Preferably, the formula (2) is selected from any one of the following chemical structures:

preferably, the refractive index of the first cover layer is between 1.9 and 3.0, and the refractive index of the second cover layer is between 1.0 and 1.8; more preferably, the refractive index of the first cladding layer is between 2.0 and 2.9 and the refractive index of the second cladding layer is between 1.05 and 1.8.

The invention provides an organic light-emitting device, which selects a triarylamine compound represented by the following formula (1) and a heterocyclic compound represented by the following formula (2) to respectively form a first covering layer and a second covering layer, wherein the corresponding compounds can be obtained by the following method:

the triarylamine compound represented by the formula (1) can be obtained by a Buchwald reaction and a Suzuki coupling reaction, namely, in a nitrogen atmosphere, adding a raw material, a catalyst, a base, a ligand and a solution, and reacting at a corresponding temperature.

A heterocyclic compound represented by formula (2), wherein, case 1: when Ar is₂₁、Ar₂₂Independently selected from one of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C3-C18 heteroaryl: the catalyst can be obtained by Suzuki coupling reaction, namely, under the nitrogen atmosphere, adding raw materials, a catalyst, inorganic base, a ligand and a solution, and reacting at a corresponding temperature;

case 2: when Ar is₂₁、Ar₂₂Independently selected from N (Q)₁)(Q₂) When the radicals are represented: can be obtained by a Buchwald reaction, namely, under the nitrogen atmosphere, adding raw materials, a catalyst, alkali, a ligand and a solution, and reacting at a corresponding temperature.

The present invention is not particularly limited with respect to the sources of the raw materials used in the above-mentioned various reactions, and the triarylamine compound represented by formula (1) and the heterocyclic compound represented by formula (2) described in the present invention can be obtained using commercially available raw materials or by a preparation method well known to those skilled in the art.

The present invention is not particularly limited to the above-mentioned reaction, and a conventional reaction known to those skilled in the art may be used.

The organic layer of the organic light-emitting device of the invention has a film thickness selected from 0.5nm to 500nm, preferably 1nm to 300nm, and a cover layer thickness selected from 10nm to 200nm, preferably 30nm to 120 nm. The film thickness of the organic layer is appropriately changed depending on the kind of material used in the organic light-emitting device and the thickness of the other layers.

The organic light emitting device of the present invention is generally formed on a substrate. The substrate may be any substrate as long as it does not change when forming an electrode or an organic layer, for example, a substrate of glass, plastic, a polymer film, silicon, or the like. When the substrate is opaque, the electrode opposite thereto is preferably transparent or translucent.

In the organic light-emitting device of the present invention, at least one of the anode and the cathode is transparent or translucent, and preferably, the cathode is transparent or translucent.

In the organic light emitting device of the present invention, the anode material may be selected from metals, such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and the like, and alloys thereof; metal oxides such as indium oxide, zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), aluminum zinc oxide, and the like; examples of the conductive polymer include polyaniline, polypyrrole, and poly (3-methylthiophene). The anode material may include other known materials suitable for an anode in addition to the above materials and combinations thereof, and examples of the production method include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like. As the anode, an organic transparent conductive film such as polyaniline or a derivative thereof, polythiophene or a derivative thereof, or the like can be used. Preferably, the anode of the present invention is selected from ITO-Ag-ITO.

In the organic light emitting device according to the present invention, the hole injection material may be a metal oxide such as molybdenum oxide, silver oxide, vanadium oxide, tungsten oxide, ruthenium oxide, nickel oxide, copper oxide, or titanium oxide, or a low molecular weight organic compound such as a phthalocyanine-based compound or a polycyano group-containing conjugated organic material, but is not limited thereto. Preferably, the hole injection layer of the present invention is selected from 4,4 '-tris [ 2-naphthylphenylamino ] triphenylamine (abbreviated as 2T-NATA), 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylamine (abbreviated as HAT-CN), 4' -tris (N, N-diphenylamino) triphenylamine (abbreviated as TDATA), 4 '-tris [ N- (3-methylphenyl) -N-phenylamino ] triphenylamine (abbreviated as MTDATA), copper (II) phthalocyanine (abbreviated as CuPc), N' -bis [4- [ bis (3-methylphenyl) amino ] phenyl ] -N, N '-diphenyl-biphenyl-4, 4' -diamine (abbreviated as DNTPD), etc., it may be a single structure made of a single substance, or a single-layer structure or a multi-layer structure made of different substances. Preferably, the hole injection layer according to the present invention is selected from copper phthalocyanine (CuPc), 4',4 ″ -tris [ 2-naphthylphenylamino ] triphenylamine (2T-NATA), 4',4 ″ -tris (N, N-diphenylamino) triphenylamine (TDATA), and the like.

In the organic light emitting device of the present invention, the hole transport material may be selected from small molecular materials such as aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, butadiene compounds, and the like, polymer materials such as poly-p-phenylene derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, polysilane and its derivatives, and the like, and a thiophene derivative provided by the present invention, but is not limited thereto. Preferably, the hole transport layer of the present invention is selected from the group consisting of N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (abbreviated as NPB), N '-di (naphthalene-1-yl) -N, N' -di (phenyl) -2,2 '-dimethylbenzidine (abbreviated as. alpha. -NPD), N' -diphenyl-N, N '-di (3-methylphenyl) -1,1' -biphenyl-4, 4 '-diamine (abbreviated as TPD), 4' -cyclohexyldi [ N, N-di (4-methylphenyl) aniline ] (abbreviated as TAPC), 2,7, 7-tetra (diphenylamino) -9, the 9-spirobifluorene (short for: Spiro-TAD) and the thiophene derivative provided by the invention can be of a single structure formed by a single substance, or of a single-layer structure or a multi-layer structure formed by different substances. Preferably, the hole transport layer according to the present invention is selected from N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB), N '-di (naphthalene-1-yl) -N, N' -di (phenyl) -2,2 '-dimethylbenzidine (α -NPD), 4' -cyclohexyldi [ N, N-di (4-methylphenyl) aniline ] (TAPC), and the like.

In the organic light-emitting device of the present invention, the material of the light-emitting layer comprisesA light-emitting layer host material AND a light-emitting layer guest material, the light-emitting layer host material may be selected from 4,4 '-bis (9-Carbazole) Biphenyl (CBP), 9, 10-bis (2-naphthyl) Anthracene (ADN), 4-bis (9-carbazolyl) biphenyl (CPB), 9' - (1, 3-phenyl) bis-9H-carbazole (mCP), 4 '-tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (alpha-AND), N' -bis- (1-naphthyl) -N, N '-diphenyl- [1,1':4', 1':4', 1' -tetrabiphenyl]-4,4' -diamino (4PNPB), 1,3, 5-tris (9-carbazolyl) benzene (TCP), and the like. In addition to the above materials and combinations thereof, the light emitting layer host material may also include other known materials suitable for use as a light emitting layer. Preferably, the light-emitting layer host material of the present invention is selected from 9, 10-bis (2-naphthyl) Anthracene (ADN), 9'- (1, 3-phenyl) bis-9H-carbazole (mCP), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA), 9, 10-bis (1-naphthyl) anthracene (α -AND), AND the like. The guest materials of the light-emitting layer of the invention are divided into blue light-emitting materials, green light-emitting materials and red light-emitting materials. The light-emitting layer guest can be selected from (6- (4- (diphenylamino (phenyl) -N, N-diphenylpyren-1-amine) (DPAP-DPPA), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 4' -bis [4- (diphenylamino) styryl]Biphenyl (BDAVBi), 4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), bis (2-hydroxyphenylpyridine) beryllium (Bepp2), bis (4, 6-difluorophenylpyridine-C2, N) picolinyliridium (FIrpic), tris (2-phenylpyridine) iridium (Ir (ppy)₃) Bis (2-phenylpyridine) iridium acetylacetonate (Ir (ppy)₂(acac)), 9, 10-bis [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), tris [ 1-phenylisoquinoline-C2, N]Iridium (III) (Ir (piq)₃) Bis (1-phenylisoquinoline) (acetylacetonato) iridium (Ir (piq))₂(acac)) and the like. In addition to the above materials, the light-emitting layer guest material may include other known materials suitable for use as a light-emitting layer. Preferably, the light emitting layer guest of the present invention is selected from 4,4' -bis [4- (di-p-tolylamino) styryl]Biphenyl (DPAVBi), 2,5,8, 11-tetra-tert-butylperylene (TBPe), 9, 10-di [ N- (p-tolyl) anilino group]Anthracene (TPA), 4- (dicyanomethylene) -2-methyl-6- (4-dimethylaminostyryl) -4H-pyran (DCM), and the like.

The doping ratio of the host material and the guest material of the light-emitting layer is preferably varied depending on the materials used, and the doping film thickness ratio of the guest material of the light-emitting layer is usually 0.01 to 20%, preferably 0.1 to 15%, more preferably 1 to 10%.

In the organic light emitting device of the present invention, the electron transport material may be selected from 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq)₃) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq), 3- (biphenyl-4-yl) -5- (4-tert-butylphenyl) -4-phenyl-4H-1, 2, 4-Triazole (TAZ), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), and the like, and the electron transport material may include other known materials suitable for an electron transport layer in addition to the above materials and combinations thereof. Preferably, the electron transport layer of the present invention is selected from 1,3, 5-tris (N-phenyl-2-benzimidazole) benzene (TPBi), tris (8-hydroxyquinoline) aluminum (III) (Alq)₃) 8-hydroxyquinoline-lithium (Liq), bis (2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BALq), and the like.

In the organic light emitting device according to the present invention, the electron injection material may Be selected from Li, Na, K, Rb, Cs, Be, Mg, Ca, lithium fluoride (LiF), sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, magnesium fluoride, calcium fluoride, lithium oxide, cesium carbonate, potassium silicate, lithium acetate, sodium acetate, potassium acetate, lithium tetrakis (8-hydroxyquinoline) boron, 8-hydroxyquinoline-lithium (Liq), and the like, and may include other known materials suitable for the electron injection layer in addition to the above materials and combinations thereof. Preferably, the electron injection layer according to the present invention is selected from lithium fluoride (LiF), 8-hydroxyquinoline-lithium (Liq), and the like.

For example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, and the like, alloys of 2 or more of these metals, or alloys of 1 or more of these metals and 1 or more of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin, graphite, or graphite intercalation compounds, and the like can be used. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. The cathode may have a laminated structure of 2 or more layers. The cathode can be prepared by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. In addition to the above materials and combinations thereof, the cathode material may also include other known materials suitable for use as a cathode. Preferably, the cathode according to the present invention is selected from semi-transparent cathodes, such as thin Ag or Mg-Ag alloys or thin Al.

Among them, when light emission of the light-emitting layer is extracted from the cathode, the light transmittance of the cathode is preferably more than 10%. It is also preferable that the sheet resistivity of the cathode is several hundred Ω · m or less, and the film thickness is usually 10nm to 500nm, preferably 10 to 100 nm.

In the organic light-emitting device according to the present invention, the capping layer includes a first capping layer and a second capping layer, and the triarylamine compound represented by formula (1) and the heterocyclic compound represented by formula (2) are preferably used. They may be formed into films alone or mixed with other materials to form films. The thickness of the first cover layer and the second cover layer is preferably 30nm to 120 nm. The first covering layer and the second covering layer can be evaporated in sequence, the first covering layer can be evaporated first, then the second covering layer can be evaporated, and then the first covering layer can be evaporated.

The film thicknesses of the hole transporting layer and the electron transporting layer may be selected as appropriate depending on the materials used, and may be selected so as to achieve appropriate values of the driving voltage and the light emission efficiency. Therefore, the film thicknesses of the hole transporting layer and the electron transporting layer are, for example, 1nm to 1um, preferably 2nm to 500nm, and more preferably 5nm to 200 nm.

The order and number of layers of the organic light-emitting device and the thickness of each layer may be appropriately selected in consideration of the light-emitting efficiency and the lifetime of the device.

The organic light-emitting device of the present invention preferably has a structure in which: substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode/first cover layer/second cover layer. However, the structure of the organic light emitting device is not limited thereto. The organic light-emitting device can be selected and combined according to the parameter requirements of the device and the characteristics of materials, and part of organic layers can be added or omitted. For example, an electron blocking layer may be provided between the hole transport layer and the light emitting layer, a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and an organic layer having the same function may be formed in a stacked structure of two or more layers.

The method for forming each layer in the organic light-emitting device is not particularly limited, and any one of vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray, slit coating, and dip coating may be used, and in the present invention, vacuum evaporation is preferably used.

The organic light-emitting device can be widely applied to the fields of panel display, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photoreceptors or organic thin film transistors, signs, signal lamps and the like.

The invention is explained in more detail by the following examples, without wishing to restrict the invention accordingly. Based on this description, one of ordinary skill in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the full scope of the disclosure without undue inventive effort.

Description of raw materials, reagents and characterization equipment:

the raw materials used in the following examples are not particularly limited, and may be commercially available products or prepared by methods known to those skilled in the art.

The mass spectrum was analyzed by matrix-assisted laser desorption ionization (AXIMA-CFR plus) from KratosAnalytical, Inc. of Shimadzu corporation, using chloroform as the solvent;

the element analysis uses a Vario EL cube type organic element analyzer of Germany Elementar company, and the mass of a sample is 5-10 mg;

EXAMPLE 1 Synthesis of Compound 1-1

Step 1: synthesis of intermediate A-1

To a 1L reaction flask were added toluene (600mL), a-1 (benzidine) (30.46g, 0.18mol), b-1 (67.54g, 0.17mol), palladium acetate (0.63g, 0.0028mol), sodium tert-butoxide (33.7g, 0.351mol), and tri-tert-butylphosphine (11mL in toluene) in that order under nitrogen. And reacted under reflux for 2 hours. After the reaction is stopped, the mixture is cooled to room temperature, filtered by using kieselguhr, the filtrate is concentrated, recrystallized by using methanol, filtered by suction and rinsed by using methanol to obtain a recrystallized solid, and the intermediate A-1(61.92g, the yield is about 75%) is obtained, and the purity of the solid is not less than 99.4% by HPLC (high performance liquid chromatography).

Step 2: synthesis of Compound 1-1

Under nitrogen protection, a 1L reaction flask was charged with toluene solvent (600ml), c-1(29.60g, 108mmol), intermediate A-1 (53.42g, 110mmol), and Pd in that order₂(dba)₃(990mg, 1.08mmol), BINAP (2.02g, 3.25mmol) and sodium tert-butoxide (9.9g, 100.8mmol), were dissolved with stirring and reacted under reflux under nitrogen for 24 hours, after completion of the reaction, the reaction solution was washed with dichloromethane and distilled water and extracted by separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, followed by washing with cyclohexane: separating, purifying and refining ethyl acetate 10:1 by column chromatography as eluent to obtain compound 1-1(49.85g, yield 68%), and solid purity ≧ 99.1% by HPLC detection.

Mass spectrum m/z: 678.29 (theoretical value: 678.27). Theoretical element content (%) C₅₀H₃₄N₂O: c, 88.47; h, 4.13; n, 4.13; o, 2.36 measured elemental content (%): c, 88.48; h, 4.14; n, 4.12; o, 2.35.

EXAMPLE 2 Synthesis of Compounds 1 to 29

Compound 1-29(48.27g, yield about 69%) was synthesized by the method described for Compound 1-1 above, and purity ≧ 99.4% by HPLC. Mass spectrum m/z: 647.30 (theoretical value: 647.27). Theoretical element content (%) C₄₅H₂₅D₅N₄O: c, 83.44; h, 5.44; n, 8.65; o, 2.47 measured elemental content (%): c, 83.45; h, 5.44; n, 8.64; o, 2.47.

EXAMPLE 3 Synthesis of Compounds 1 to 66

Compound 1-66(42.46g, yield about 70%) was synthesized by the method described for Compound 1-1 above, and purity ≧ 99.5% by HPLC. Mass spectrum m/z: 647.30 (theoretical value: 647.27). Theoretical element content (%) C₃₆H₂₃N₃O₂S: c, 76.99; h, 4.13; n, 7.48; o, 5.70; s, 5.71 measured element content (%): c, 76.96; h, 4.13; n, 7.49; o, 5.73; and S, 5.70.

EXAMPLE 4 Synthesis of Compounds 1 to 78

Compound 1-78(43.89g, yield about 66%) was synthesized by the method described for Compound 1-1 above, and purity ≧ 99.2% by HPLC. Mass spectrum m/z: 615.20 (theoretical value: 615.19). Theoretical element content (%) C₄₃H₂₅N₃O₂: c, 83.88; h, 4.09; n, 6.83; o, 5.20 measured elemental content (%): c, 83.89; h, 4.08; n, 6.82; and O, 5.21.

EXAMPLE 5 Synthesis of Compounds 1 to 83

Compound 1-83(47.59g, yield about 65%) was synthesized by the method described for Compound 1-1 above, and purity ≧ 99.3% by HPLC. Mass spectrum m/z: 677.36 (theoretical value: 677.30). Theoretical element content (%) C₄₇H₃₉N₃O₂: c, 83.28; h, 5.80; n, 6.20; o, 5.21 measured elemental content (%): c, 83.29; h, 5.80; n, 6.20; and O, 5.20.

EXAMPLE 6 Synthesis of Compounds 1-108

Compound 1-108(51.30g, yield about 63%) was synthesized by the method described above for Compound 1-1, and purity ≧ 99.8% by HPLC. Mass spectrum m/z: 753.36 (theoretical value: 753.31). Theoretical element content (%) C₅₆H₃₉N₃: c, 89.21; h, 5.21; n, 5.57 measured elemental content (%): c, 89.22; h, 5.22; and N, 5.55.

EXAMPLE 7 Synthesis of Compounds 1 to 128

Compound 1-128(38.70g, yield about 65%) was synthesized by the method described for Compound 1-1 above, and purity ≧ 98.8% by HPLC. Mass spectrum m/z: 551.18 (theoretical value: 551.15). Theoretical element content (%) C₃₅H₂₅N₃S₂: c, 76.19; h, 4.57; n, 7.62; s, 11.62 measured element content (%): c, 76.21; h, 4.58; n, 7.60; s, 11.61.

EXAMPLE 8 Synthesis of Compounds 1 to 180

Compound 1-180(34.67g, yield about 64%) was synthesized by the method described for Compound 1-1 above, and purity ≧ 99.2% by HPLC. Mass spectrum m/z: 501.12 (theoretical value: 501.10). Theoretical element content (%) C₃₀H₁₉N₃OS₂: c, 71.83; h, 3.82; n, 8.38; o, 3.19; s, 12.78 measured element content (%): c, 71.84; h, 3.83; n, 8.38; o, 3.18; s, 12.77.

EXAMPLE 9 Synthesis of Compounds 1 to 214

Compound 1-214(46.25g, yield about 60%) was synthesized by the method described for Compound 1-1 above, and purity ≧ 99.3% by HPLC. Mass spectrum m/z: 713.32 (theoretical value: 713.28). Theoretical element content (%) C₅₃H₃₅N₃: c, 89.17; h, 4.94; n, 5.89 measured elemental content (%): c, 89.19; h, 4.92; and N, 5.89.

EXAMPLE 10 Synthesis of Compounds 1 to 227

Compound 1-227(39.90g, 61% yield) was synthesized by the method described for Compound 1-1 above, and had a solid purity of 99.0% or more by HPLC.

Mass spectrum m/z: 605.27 (theoretical value: 605.21). Theoretical element content (%) C₄₂H₂₇N₃O₂: c, 83.29; h, 4.49; n, 6.94; o, 5.28 measured elemental content (%): c, 83.30; h, 4.49; n, 6.93; and O, 5.28.

By way of example as above, the compounds thus obtained are as follows:

EXAMPLE 11 Synthesis of Compound 2-1

Synthesis of intermediate I-2-1

To a 1L reaction flask, toluene (600mL), compound 2-m (57.56g, 0.21mol), compound 2-n (19.56g, 0.21mol), palladium acetate (0.61g, 0.0027mol), sodium tert-butoxide (33.7g, 0.351mol), and tri-tert-butylphosphine (10.7mL in toluene) were added in that order under nitrogen. And reacted under reflux for 2 hours. After the reaction is stopped, the mixture is cooled to room temperature, filtered by using kieselguhr, the filtrate is concentrated, recrystallized by using methanol, filtered by suction and rinsed by using methanol to obtain a recrystallized solid, and the intermediate I-2-1(48.71g, the yield is about 81 percent) is obtained, and the purity of the solid is not less than 99.3 percent by HPLC (high performance liquid chromatography).

Synthesis of Compound 2-1

A1L reaction flask was charged with toluene solvent (450ml), compound 2-q (11.74g, 36mmol), intermediate I-2-1(22.33g, 78mmol), and Pd in that order₂(dba)₃(1.00g, 1.10mmol), BINAP (1.67g, 16.7mmol) and sodium tert-butoxide (9.9g, 100.8mmol), dissolved with stirring, and reacted under reflux under a nitrogen atmosphere for 24 hours, after completion of the reaction, the reaction solution was washed with dichloromethane and distilled water, and subjected to extraction by separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, followed by washing with cyclohexane: separating, purifying and refining ethyl acetate 10:1 by column chromatography as eluent to obtain solid compound 2-1(23.90g, yield 84%), and purity ≧ 99.4% by HPLC.

Mass spectrum m/z: 736.27 (theoretical value: 736.25). Theoretical element content (%) C₅₀H₃₂N₄O₃: c, 81.50; h, 4.38; n, 7.60; o, 6.51 measured elemental content (%): c, 81.52; h, 4.37; n, 7.60; and O, 6.50.

EXAMPLE 12 Synthesis of Compounds 2 to 12

Compound 2-12(21.01g, yield about 79%) was synthesized by the method described for Compound 2-1 above, and purity ≧ 99.3% by HPLC. Mass spectrum m/z: 752.25 (theoretical value: 752.22). Theoretical element content (%) C₅₀H₃₂N₄O₂S: c, 79.77; h, 4.28; n, 7.44; o, 4.25; s, 4.26 measured element content (%): c, 79.79; h, 4.27; n, 7.43; o, 4.25; and S, 4.26.

EXAMPLE 13 Synthesis of Compounds 2 to 36

Compound 2-36(18.04g, yield about 81%) was synthesized by the method described for Compound 2-1 above, and purity ≧ 99.5% by HPLC. Mass spectrum m/z: 618.15 (theoretical value: 618.13). Theoretical element content (%) C₃₆H₂₂N₆OS₂: c, 69.88; h, 3.58; n, 13.58; o, 2.59; s, 10.36 measured element content (%): c, 69.89; h, 3.56; n, 13.58; o, 2.59; s, 10.38.

EXAMPLE 14 Synthesis of Compounds 2 to 46

Compound 2-46(25.25g, yield about 78%) was synthesized by the method described for Compound 2-1 above, and purity ≧ 99.4% by HPLC. Mass spectrum m/z: 898.38 (theoretical value: 898.34). Theoretical element content (%) C₆₃H₄₂N₆O: c, 84.16; h, 4.71; n, 9.35; o, 1.78 measured elemental content (%): c, 84.18; h, 4.72; n, 9.34; o, 1.76.

EXAMPLE 15 Synthesis of Compounds 2 to 68

Compound 2-68(18.09g, yield about 74%) was synthesized by the method described above for Compound 2-1, and purity ≧ 99.0% by HPLC. Mass spectrum m/z: 678.29 (theoretical value: 678.25). Theoretical element content (%) C₄₄H₃₄N₄O₂Si: c, 77.85; h, 5.05; n, 8.25; o, 4.71; si, 4.14 measured elemental content (%): c, 77.86; h, 5.04; n, 8.25; o, 4.72; si, 4.13.

EXAMPLE 16 Synthesis of Compounds 2 to 89

Compound 2-89(21.09g, yield about 77%) was synthesized by the method described for Compound 2-1, and purity ≧ solid purity by HPLC99.2 percent. Mass spectrum m/z: 760.38 (theoretical value: 760.34). Theoretical element content (%) C₅₁H₄₄N₄O₃: c, 80.50; h, 5.83; n, 7.36; o, 6.31 measured elemental content (%): c, 80.50; h, 5.83; n, 7.35; o, 6.32.

EXAMPLE 17 Synthesis of Compounds 2 to 95

Step 1: synthesis of intermediate B-95

To a 1L reaction flask were added toluene (600mL), x-2-95 (benzidine) (24.15g, 0.18mol), y-2-95(69.92g, 0.17mol), palladium acetate (0.63g, 0.0028mol), sodium tert-butoxide (24.1g, 0.251mol), and tri-tert-butylphosphine (11mL in toluene) in that order under nitrogen. And reacted under reflux for 2 hours. After the reaction is stopped, the mixture is cooled to room temperature, filtered by using kieselguhr, the filtrate is concentrated, recrystallized by using methanol, filtered by suction and rinsed by using methanol to obtain a recrystallized solid, and the intermediate B-95(51.33g, the yield is about 65%) is obtained, and the purity of the solid is not less than 99.1% by HPLC (high performance liquid chromatography).

Step 2: synthesis of Compounds 2-95

Under nitrogen protection, a 1L reaction flask was charged with toluene solvent (600ml), z-2-95(11.52g, 32mmol), intermediate B-95(15.48g, 33.3mmol), and Pd in that order₂(dba)₃((439.5mg, 0.48mmol)), BINAP (0.89g, 1.04mmol) and sodium tert-butoxide (9.9g, 100.8mmol) were dissolved with stirring and reacted under reflux under a nitrogen atmosphere for 24 hours, and after completion of the reaction, the reaction solution was washed with dichloromethane and distilled water and subjected to extraction by separation. The organic layer was dried over anhydrous magnesium sulfate, filtered, and then the solvent was removed, followed by washing with cyclohexane: separating, purifying and refining ethyl acetate 10:1 by column chromatography as eluent to obtain compound 2-95(19.92g, yield about 79%), and solid purity ≧ 99.1% by HPLC. Mass spectrum m/z: 787.33 (theoretical value: 787.29). Theoretical element content (%) C₅₄H₃₇N₅O₂: c, 82.32; h, 4.73; n, 8.89; o, 4.06 measured elemental content (%): c, 82.33; h, 4.72；N，8.88；O，4.07。

EXAMPLE 18 Synthesis of Compounds 2 to 121

Compound 2-121(15.01g, yield about 86%) was synthesized by the method described above for Compound 2-95, and purity ≧ 99.4% by HPLC. Mass spectrum m/z: 581.18 (theoretical value: 581.17). Theoretical element content (%) C₃₉H₂₃N₃O₃: c, 80.54; h, 3.99; n, 7.22; o, 8.25 measured elemental content (%): c, 80.55; h, 3.99; n, 7.21; and O, 8.25.

EXAMPLE 19 Synthesis of Compounds 2 to 153

To a 1L reaction flask were added the compound h-2-153(14.70g, 35mmol), the compound p-2-153(13.17g, 35mmol), palladium tetrakistriphenylphosphine (1.15g, 1mmol) and sodium carbonate (41.0g, 300mmol) in this order under nitrogen protection, and the weighed reactants were dissolved in a solvent of toluene (1L)/EtOH (200 mL)/distilled water (200mL) and heated at 90 ℃ for 2 hours. The reaction mixture was cooled to room temperature, diluted with toluene and filtered through celite. The filtrate was diluted with water and extracted with toluene, and the organic phases were combined and evaporated under vacuum. The residue was filtered through silica gel and recrystallized. Compound 2-153(19.54g, 78% yield) was obtained with a solid purity ≧ 99.5% by HPLC. Mass spectrum m/z: 715.28 (theoretical value: 715.26). Theoretical element content (%) C₅₂H₃₃N₃O: c, 87.25; h, 4.65; n, 5.87; o, 2.23 measured element content (%): c, 87.25; h, 4.65; n, 5.85; o, 2.25.

EXAMPLE 20 Synthesis of Compounds 2-169

Compound 2-169(17.97g, yield about 80%) was synthesized by the method described for Compound 2-153 above, and purity ≧ 99.4% by HPLC. Mass spectrum m/z: 641.28 (theoretical value: 641.24). Theoretical element content (%) C₄₇H₃₁NO₂: c, 87.96; h, 4.87; n, 2.18; measured element content of O, 4.99(％)：C，87.98；H，4.89；N，2.16；O，4.97。

By way of example as above, the compounds thus obtained are as follows:

refractive index (n) was measured by j.a.woollam, usa, model: measuring by an M-2000 spectrum ellipsometer, wherein the measurement is in an atmospheric environment, and the scanning range of the ellipsometer is 245-1000 nm; the size of the glass substrate is 200 multiplied by 200mm, and the thickness of the material film is 20-60 nm. The arylamine compound and the prior material are respectively tested for thermal performance and refractive index, and the results are shown in the following table 1.

TABLE 1 photophysical characteristic test of light emitting device

Cover material	Refractive index n @450nm	Cover material	Refractive index n @450nm
				Compound 1-1	2.29	Compound 2-1	1.74
Compounds 1 to 29	2.20	Compounds 2 to 12	1.69
				Compounds 1 to 66	2.10	Compounds 2 to 36	1.75
Compounds 1 to 78	2.18	Compounds 2 to 46	1.68
				Compounds 1 to 83	2.33	Compounds 2 to 68	1.50
Compounds 1 to 108	2.27	Compounds 2 to 89	1.60
				Compounds 1 to 128	2.16	Compound 2-95	1.73
Compounds 1 to 180	2.09	Compounds 2 to 121	1.78
				Compounds 1 to 214	2.45	Compounds 2 to 153	1.79
Compounds 1 to 227	2.24	Compound 2-169	1.64

Compounds 1-1, 1-29, 1-66, 1-78, 1-83, 1-108, 1-128, 1-180, 1-214, 1-227, were used as a first capping layer for an OLED device, compounds 2-1, 2-12, 2-36, 2-46, 2-68, 2-89, 2-95, 2-121, 2-153, 2-169, were used as a second capping layer for an OLED device.

Comparative examples 1-2 device preparation examples:

the organic light-emitting device is prepared by a vacuum thermal evaporation method. The experimental steps are as follows: repeatedly washing the ITO-Ag-ITO substrate with a glass cleaning agent, then washing the ITO-Ag-ITO substrate in distilled water for 2 times, ultrasonically washing for 15 minutes, after the washing with the distilled water is finished, ultrasonically washing solvents such as isopropanol, acetone and methanol in sequence, drying at 120 ℃, and conveying to an evaporation plating machine.

Evaporating a hole injection layer HAT-CN/45nm, an hole transport layer NPB/40nm, an emitting layer (host ADN: mixed with DPAP-DPPA 8%)/30 nm, an electron transport layer TPBi/30nm, an electron injection layer LiF/1nm and a cathode Mg-Ag (Mg: Ag doping ratio of 9:1)/20 nm) on a prepared ITO-Ag-ITO electrode in a layer-by-layer vacuum evaporation manner, and then evaporating a cover material Alq on a cathode layer₃/60nm。

Comparative example 2: the cover material Alq in comparative example 1₃The same procedure was followed with the compound CP-1, to obtain a comparative organic light-emitting device 2.

[ application examples 1 to 20]

Application example 1: coating material Alq of organic light-emitting device₃In exchange for the present inventionCompound 1-1 in examples 1-10 and compound 2-1 in examples 11-20 of the present invention.

Application example 2: coating material Alq of organic light-emitting device₃The compounds 1 to 29 in examples 1 to 10 of the present invention and the compounds 2 to 12 in examples 11 to 20 of the present invention were replaced.

Application example 3: coating material Alq of organic light-emitting device₃The compounds 1 to 66 in examples 1 to 10 of the present invention and the compounds 2 to 36 in examples 11 to 20 of the present invention were replaced.

Application example 4: coating material Alq of organic light-emitting device₃The compounds 1 to 78 in examples 1 to 10 of the present invention and the compounds 2 to 46 in examples 11 to 20 of the present invention were replaced.

Application example 5: coating material Alq of organic light-emitting device₃The compounds 1 to 83 in examples 1 to 10 of the present invention and the compounds 2 to 68 in examples 11 to 20 of the present invention were replaced.

Application example 6: coating material Alq of organic light-emitting device₃The compounds 1 to 108 in examples 1 to 10 of the present invention and the compounds 2 to 89 in examples 11 to 20 of the present invention were replaced.

Application example 7: coating material Alq of organic light-emitting device₃The compounds 1 to 128 in examples 1 to 10 of the present invention and the compounds 2 to 95 in examples 11 to 20 of the present invention were replaced.

Application example 8: coating material Alq of organic light-emitting device₃The compounds 1 to 180 in examples 1 to 10 of the present invention and the compounds 2 to 121 in examples 11 to 20 of the present invention were replaced.

Application example 9: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in examples 1 to 10 of the present invention and compounds 2 to 153 in examples 11 to 20 of the present invention.

Application example 10: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 227 in examples 1 to 10 of the present invention and compounds 2 to 169 in examples 11 to 20 of the present invention.

Application example 11: coating material Alq of organic light-emitting device₃In exchange for the present inventionCompounds 1-214 in examples 1-10 and compounds 2-1 in examples 11-20 of this invention.

Application example 12: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in examples 1 to 10 of the present invention and compounds 2 to 12 in examples 11 to 20 of the present invention.

Application example 13: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in inventive examples 1 to 10 and compounds 2 to 36 in inventive examples 11 to 20.

Application example 14: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in examples 1 to 10 of the present invention and compounds 2 to 46 in examples 11 to 20 of the present invention.

Application example 15: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in inventive examples 1 to 10 and compounds 2 to 68 in inventive examples 11 to 20.

Application example 16: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in inventive examples 1 to 10 and compounds 2 to 89 in inventive examples 11 to 20.

Application example 17: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in examples 1 to 10 of the present invention and compounds 2 to 95 in examples 11 to 20 of the present invention.

Application example 18: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in inventive examples 1 to 10 and compounds 2 to 121 in inventive examples 11 to 20.

Application example 19: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in examples 1 to 10 of the present invention and compounds 2 to 153 in examples 11 to 20 of the present invention.

Application example 20: coating material Alq of organic light-emitting device₃The procedure was changed to compounds 1 to 214 in examples 1 to 10 of the present invention and compounds 2 to 169 in examples 11 to 20 of the present invention.

The test software, computer, K2400 digital source meter manufactured by Keithley corporation, usa, and PR788 spectral scanning luminance meter manufactured by Photo Research corporation, usa were combined into a combined IVL test system to test the luminous efficiency and CIE color coordinates of the organic light emitting device.

The results of the light emission characteristic test of the obtained organic light emitting device are shown in table 2. Table 2 shows the results of the test of the light emitting characteristics of the light emitting devices prepared by the compounds prepared in the examples of the present invention and the comparative materials.

Table 2 test of light emitting characteristics of light emitting device

As can be seen from the results of table 2, the organic light emitting device of the present invention, which uses the first capping layer and the second capping layer together as the capping layer material, exhibits an advantage of high light emitting efficiency as compared to comparative examples 1-2, and is an organic light emitting material having good performance.

It should be understood that the present invention has been particularly described with reference to particular embodiments thereof, but that various changes in form and details may be made therein by those skilled in the art without departing from the principles of the invention and, therefore, within the scope of the invention.

Claims

1. An organic light-emitting device comprising an anode electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a cathode electrode, and a cover layer in this order, wherein the cover layer comprises a first cover layer and a second cover layer, and wherein the refractive index of the first cover layer is 1.9 or more and the refractive index of the second cover layer is 1.0 or more in the range of 400nm to 750nm in the wavelength of light transmitted through the cover layer; the first cover layer contains a triarylamine compound represented by formula (1),

R₂selected from hydrogen, deuterium,One of methyl, ethyl, n-propyl, isopropyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, dibenzothienyl, and dibenzofuranyl;

wherein, X₁Selected from O, S, SiR 'R', Se, CR 'R' or

Y and Z are each independently hydrogen or deuterium, or Y and Z together form a bond, or-W-, wherein W is O, S, SiR "R", CR "R"; x₂The compound is selected from a single bond, O, S or CR ' R ', wherein R ' is selected from one of methyl, ethyl, isopropyl, tert-butyl, phenyl, dibenzofuranyl, dibenzothienyl, furyl, thienyl, benzofuranyl and benzothienyl; r' is selected from one of H, methyl, ethyl, isopropyl, tert-butyl, phenyl, dibenzofuranyl and dibenzothienyl; r' is selected from one of H, methyl, ethyl, isopropyl, tert-butyl, phenyl, dibenzofuranyl and dibenzothienyl;

m is 0,1 or 2, n is 0,1 or 2, and m + n is more than or equal to 1.

2. The organic light-emitting device of claim 1, wherein Ar is Ar₁Is one of the following groups:

wherein, Ar is₄、Ar₅、Ar₆、Ar₇、Ar₈、Ar₉、Ar₁₀、Ar₁₁、Ar₁₂、Ar₁₃、Ar₁₄、Ar₁₅、Ar₁₆、Ar₁₇、Ar₁₈、Ar₁₉、Ar₂₀Each independently represents one of hydrogen, deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, benzothienyl, benzofuranyl, dibenzothienyl and dibenzofuranyl; ar (Ar)₄、Ar₅、Ar₆、Ar₇、Ar₈、Ar₉、Ar₁₀、Ar₁₁、Ar₁₂、Ar₁₃、Ar₁₄、Ar₁₅、Ar₁₆、Ar₁₇、Ar₁₈、Ar₁₉、Ar₂₀May be the same or different;

p is 0,1 or 2;

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

3. the organic light-emitting device of claim 1, wherein Ar is Ar₁One selected from the group shown below:

4. the organic light-emitting device of claim 1, wherein Ar is Ar₂、Ar₃Independently selected from one of the following groups:

R₁₃selected from deuterium, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, phenyl,One of tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, acridinyl, spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, benzothienyl, benzofuranyl, dibenzothiophenyl, and dibenzofuranyl;

e is selected from an integer of 0 to 2;

a is selected from an integer of 0 to 3;

c is an integer from 0 to 4;

b is an integer from 0 to 5;

d is an integer from 0 to 7;

f is an integer from 0 to 9.

5. The organic light-emitting device of claim 1, wherein Ar is Ar₂、Ar₃Independently selected from one of the following groups:

6. the organic light-emitting device according to claim 1, wherein the formula (1) is selected from any one of the following chemical structures:

7. the organic light-emitting device according to claim 1, wherein the formula (2) is one selected from the following formulae (2) -1 to (2) -14:

8. the organic light-emitting device according to claim 1, wherein the Ar is₂₁、Ar₂₂Independently selected from n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or unsubstituted perylene, substituted or unsubstituted indenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted pyrenylA thiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted benzospirofluorenyl group, a substituted or unsubstituted phenylfluorenyl group,

wherein the substituent in the substituted phenyl, substituted naphthyl, substituted anthracenyl, substituted phenanthrenyl, substituted triphenylenyl, substituted pyrenyl, substituted perylenyl, substituted indenyl, substituted pyrrolyl, substituted imidazolyl, substituted oxazolyl, substituted thiazolyl, substituted pyridyl, substituted pyrimidinyl, substituted triazinyl, substituted benzofuranyl, substituted benzothienyl, substituted indolyl, substituted quinolinyl, substituted isoquinolinyl, substituted quinazolinyl, substituted benzimidazolyl, substituted benzoxazolyl, substituted acridinyl, substituted phenazinyl, substituted phenothiazinyl, substituted phenoxazinyl, substituted fluorenyl, substituted carbazolyl, substituted dibenzofuranyl, substituted dibenzothienyl, substituted spirofluorenyl, substituted benzospirofluorenyl, substituted phenylfluorenyl is methyl, Ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl,

or from N (Q)₁)(Q₂) One of the groups represented, wherein Q₁And Q₂Independently of each otherSelected from deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, indenyl, pyrenyl, perylenyl, one of fluoranthenyl, triphenylene, pyridyl, pyranyl, thienyl, furyl, pyrrolyl, imidazolyl, imidazolinyl, pyrazolyl, pyrazolinyl, pyridazinyl, pyrazinyl, piperidyl, piperazinyl, quinolyl, isoquinolyl, benzofuryl, benzothienyl, indolyl, carbazolyl, benzoxazolyl, benzothiazolyl, quinoxalyl, benzimidazolyl, pyrazolyl, dibenzofuryl, dibenzothienyl and carbolinyl.

9. The organic light-emitting device according to claim 1, wherein the formula (2) is selected from any one of the following chemical structures:

10. the organic light emitting device of claim 1, wherein the first cladding layer has a refractive index of between 1.9 and 3.0 and the second cladding layer has a refractive index of between 1.0 and 1.8.